Indian Patents
Title of Invention

ARYL-PYRIDINE COMPOUNDS
Abstract This invention is concerned with aryl-pyridine compounds of formula (I) as well as pharmaceutically acceptable salts and esters thereof, wherein R1 to R7, A, E and G have the significance given in claim 1 can be used in the form of pharmaceutical compositions.
Full Text The present invention is concerned with aryl-pyridine compounds useful as 11ß-HSD1 inhibitors (T2D).
The invention is concerned particularly with compounds of formula (I)
(Formula Removed)
and pharmaceutically acceptable salts and esters thereof, wherein
R1 is hydrogen, alkyl, cycloalkyl, hydroxy, hydroxyalkyl, alkoxy, alkoxyalkyl, amino or aminoalkyl;
R2 is hydrogen, alkyl or halogen;
R3 is hydrogen, alkyl or halogen;
R4 is phenyl, naphtyl, thiophenyl, pyridyl, quinolyl, piperidyl, morpholyl, thiomorpholyl optionally substituted with one or more substituents independently selected from alkyl, cycloalkyl, halogen, hydroxy, hydroxyalkyl, alkoxy, alkoxyalkyl, hydroxyalkoxy, alkoxyalkoxy, cyano, trifluoromethyl, trifluoromethoxy, aryl, arylalkyl, aryloxy, heterocyclyl, alklylcarbonylamino, alkoxycarbonylalkoxy and alkyl-SO2-;
R5 is hydrogen or alkyl;
R , R7, R8, R9 and R10 are independently selected from hydrogen, alkyl, halogen, cyano, trifluoromethyr, alkoxy ana aLkyl-
A is nitrogen or C-R10;
E is nitrogen or C-R9;
G is nitrogen or C-R8; and
wherein not more than one of A, E and G is nitrogen.
Glucocorticoids (cortisol in humans, corticosterone in mice and rats) are an important class of adrenocorticosteroids that regulate many metabolic and homeostatic processes and form a key component of the response to stress. Glucocorticoids act via intracellular glucocorticoid receptors and, in some tissues, mineralocorticoid receptors; both being nuclear transcription factors. Glucocorticoid action on target tissues depends not only on circulating steroid concentrations and the cellular expression of receptors, but also on intracellular enzymes that critically determine to which extent glucocorticoids gain access to receptors in an active forms, llbeta-hydroxysteroid dehydrogenases (llbeta-HSD's) catalyze the interconversion of the principal active ll-hydroxy-glucocorticoid (Cortisol in men) and their inactive 11-keto metabolites (cortisone in men).
The enzyme 1 Ibeta-hydroxysteroid dehydrogenase type 1 (1 Ibeta-HSDl) inter-converts inactive into active glucocorticoids, thereby playing a major role in local modulation of cellular agonist concentration and thus activation of corticosteroid receptors in target tissues. In a recent study made by F. Hoffmann-La Roche 'differences in gene expression in lean and obese men were analyzed using gene array technology in order to identify specific changes in gene expression that might be associated with insulin resistance or altered metabolism. This study revealed that the rnRNA for 1 Ibeta-HSDl is approximately two-fold up regulated in adipose tissue in obese individuals. Moreover, overexpressing llbeta-HSDl in adipocytes of mice led to visceral obesity and to a syndrome-X like phenotype (Masuzaki H. et al., Science. 2001 Dec 7; 294(5549):2166-70.). Taken together, these data very strongly support an important role of 1 Ibeta-HSDl in the induction of obesity and the impairment of glucose homeostasis and lipid parameters. Thust selective inhibition of this enzyme could lower blood glucose levels in Type 2
diabetic patients, normalize elevated lipid parameters and/or reduce weight in obese subjects.
The first pharmacological indication that llbeta-H5L>i inniDinon in men might have beneficial effects were obtained by using carbenoxolone, an anti-ulcer drug which inhibits both llbeta-HSDl and the related enzyme llbeta-HSD2. Treatment with carbenoxolone led to an increase in insulin sensitivity indicating that that inhibition of 1 Ibeta-HSDl may reduce cellular cortisol levels and therefore minimizing some of its deleterious effects. (Walker et al. 1995; J. Clin. Endocrinol. Metab. 80,31155-3159).
1 Ibeta-HSDl is expressed in many tissues including liver, adipose tissue, vascular smooth muscles, pancreas and brain. Its activity is dependent on NADP(H) and it has a relatively low affinity for its substrate (compared to llbeta-HSD2). 11 beta-HSDl in tissue homogenates and when purified is bidirectional, exhibiting both llbeta-dehydrogenase and llbeta-reductase reactions, with greater stability of the dehydrogenase activity (P.M. Stewart and Z.S. Krozowski, Vitam. Horm. 57 (1999), pp. 249-324). However, when the enzyme activity is tested in intact cells, the llbeta-reductase activity predominates, which regenerates active glucocorticoids from inert 11-keto forms. Suchglucocorticoid regeneration will increase effective intracellular glucocorticoid levels and thereby amplifying glucocorticoid activity. It is this elevated cellular cortisol concentration that might lead to increased hepatic glucose production, adipocyte differentiation and insulin resistance.
Inhibition of llbeta-HSDl should not only reduce the typical Syndrome-X / Diabetes associated symptoms, but it should also be save and without major side effect Studies with the unspetific inhibitor carbenoxolone. highlight the importance of developing specific llbeta-HSDl inhibitors. The inhibition of the llbeta-HSD2 enzyme is badly tolerated and results in increased blood pressure. In contrast inhibition of llbeta-HSDl should be well tolerated since llbeta-HSDl knockout mice were found be healthy and to resist hyperglycemia provoked by obesity or stress (Kotelevtsev Y. et aL, Proc Nati Acad Sci USA. 1997 Dec 23;94(26):14924-9). Similar upon starvation these mice had attenuated activation of key hepatic enzymes that are involved in gluconeogenesis. In addition, these mice had improved lipid and lipoprotein profiles suggesting that inhibition of HSD1 might be highly efficacious and safe. Recent reports indicate that llbeta-HSDl inhibitors might also be beneficial to reduce high blood pressure (Masuzaki H. et al., J Clin Invest. 2003 July,112(l):83-90; Rauz S. et al., QJM. 2003 July;96(7):481-90) to improve
cognition (Sandeep TC. et al., Proc Natl Acad Sci U S A. 2004 Apr. 27;101(17):6734-9) or to improve Alzheimer associated deficits. Taken together llbeta-HSDl inhibition might be a save and efficacious approach to treat symptoms of diabetes, obesity and other diseases.
The compounds of formula I and their pharmaceutically acceptable salts and esters are novel and have valuable pharmacological properties. In particular they are 1 Ib-HSDl inhibitors (T2D) and they display selectivity against the related llbeta-HSD2 enzyme. Therefore the compounds which are specific llbeta-HSDl inhibitors (T2D) represent an approach to e.g. lower blood glucose levels and normalize lipid parameters in Type 2 diabetic patients by modulating the local concentration of the active glucocorticoid cortisol in target tissue (liver, adipose tissue).
The compounds of the present invention can be used in the prophylaxis and/or treatment of metabolic disorders, obesity, dyslipidemiae, hypertension and/or diabetes, particularly diabetes Type II.
The compounds of this invention can further be used in the prophylaxis and/or treatment of high ocular eye pressure, cognition, Alzheimer and/or neurodegeneration.
Objects of the present invention are the compounds of formula I and their aforementioned salts and esters per se and their use as therapeutically active substances, a process for the manufacture of the said compounds, intermediates, pharmaceutical compositions, medicaments containing the said compounds, their pharmaceutically acceptable salts and esters, the use of the said compounds, esters and salts for the prophylaxis and/or therapy of illnesses, especially in the treatment or prophylaxis of eating disorders, obesity, dyslipidemiae, hypertension and/or diabetes, particularly diabetes Type II, and the use of the said compounds, salts and esters for the production of medicaments for the treatment or prophylaxis of metabolic disorders, obesity, dyslipidemiae, hypertension and/or diabetes, particularly diabetes Type II.
The compounds of the present invention can further be combined with PPAR (alpha, gamma, delta) agonists, DHEA (dehydroepiandrosterone), DPPIV inhibitors, insulin and/or lipase inhibitors, particularly orlistat.
In the present description the term "alkyl", alone or in combination, signifies a straight-chain or branched-chain alkyl group with 1 to 8 carbon atoms, preferably a straight or branched-chain alkyl group with 1 to 6 carbon atoms and particularly preferred
a straight or branched-chain alkyl group with 1 to 4 carbon atoms Examples of straight-chain and branched Q-Cg alkyl groups are methyl, ethyl, propyl, isopropyi, butyl, isobutyl, tert.-butyl, the isomeric pentyls, the isomeric hexyls, the isomeric heptyls and the isomeric octyls, preferably methyl and ethyl and most preferred methyl.
The term "cycloalkyl", alone or in combination, signifies a cydoalkyl ring with 3 to 8 carbon atoms and preferably a cydoalkyl ring with 3 to 6 carbon atoms. Examples of Cs-Cs cydoalkyl are cydopropyl, methyl-cydopropyi, dimethylcydopropyl, cydobutyl, methyl-cydobutyl, cydopentyl, memyi-cydopentyl, cydohexyl, methyl-cydohexyl, dimethyl-cydohexyl, cydoheptyl and cydooctyl, preferably cydopropyl. • •,
The term "alkoxy", alone or in combination, signifies a group of the formula alkyl-O- in which the term "alkyl" has the previously given significance, such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec butoxy and tertbutoxy, preferably methoxy and ethoxy and most preferred methoxy.
The term "hydroxyalkyT, alone or in combination, signifies an alkyl group as defined before, wherein one or more hydrogen atoms, preferably one hydrogen atom is replaced by a hydroxy group. Examples of hydrdxyalkyl are hydroxymethyl and hydroxyethyi.
The term "aryl", alone or in combination, signifies a phenyl or naphthyl group, preferably a phenyl group which optionally carries one or more substituents, preferably one to three, each independently sdected from halogen, trifluoromethyl, trifluoromethoxy, amino, alkyl, alkoxy, alkylcarbonyl, cyano, carbamoyl, alkoxycarbamoyl, methylendioxy, carboxy, alkoxycarbonyl, aminocarbonyl, alkyaminocarbonyl, dialkylaminocarbonyl, hydroxy, nitro, alkyl-SOi-, amino-SO2-, cydoalkyl and the like. Preferred is phenyl or naphthyl, particularly phenyl optionally substituted with one to three, preferably one or two substituents independently selected from alkyl, halogen, alkoxy, trifluoromethoxy, nitro and trifluoromethyl. Particularly preferred is phenyl.
The term "aryloxy", alone or in combination, signifies a aryl-O- group in which the term "aryl" has the previously given significance.
The term "heterocydyT, alone or in combination signifies a saturated, partially unsaturated or aromatic 5- to 10-membered heterocyde which contains one or more hetero atoms selected from nitrogen, oxygen and sulphur. If desired, it can be substituted
on one or more carbon atoms e.g. by halogen, alkyi, alkoxy, oxo etc. and/or on a secondary nitrogen atom (i.e. -NH-) by alkyi, cydoalkyl, aralkoxycarbonyl, alkanoyl, phenyl or phenylalkyl or on a tertiary nitrogen atom (i.e.=N-) by oxido, with halogen, alkyi, cydoalkyl and alkoxy being preferred. Examples of such heterocydyl groups are pyrrolidinyl, piperidinyl, piperazinyl, morpholinyl, thiomorpholinyl, pyrazoyl, imidazoyl (e.g. imidazol-4-yl and 1-benzyloxycarbonyl- imidazol-4-yl), pyrazoyl, pyridyl, pyrazinyl, pyrimidinyl, hexahydro-pyrimidinyl, furyl, thienyl, thiazolyl, oxazolyl, indolyl (e.g. 2-indolyl), quinolyl (e.g. 2*quinolyi, 3-quinolyl and l-oxido-2-quinolyl), isoquinolyl (e.g. 1-isoquinolyl and 3-isoquinolyl), tetrahydroquinolyi (e.g.l,2,3,4-tetrahydro-2-quinolyi), 1,2,3,4-tetrahydroisoquinolyl (e.g. 1,2,3,4-tetrahydro-1-oxo-isoquinolyl) and quinoxalinyl. Preferred examples are thiophenyl, quinolyl, piperidyl, morpholyl, thiomorpholyi, oxazolyl, pyridinyl, pyrimidinyl, pyrazolyl, imidazolyl and thiazolyl.
The term "amino", alone or in combination, signifies a primary, secondary or tertiary amino group bonded via the nitrogen atom, with the secondary amino group carrying an alkyi or cydoalkyl substituent and the tertiary amino group carrying two similar or different alkyi or cydoalkyl substituents or the two nitrogen substitutents together forming a ring, such as, for example, -NHz, methylamino, ethylamino, dimethylamino, diethylamino, methyl-ethylamino, pyrrolidin-1-yl or piperidino etc., preferably primary amino, dimethylamino and diethylamino and particularly dimethylamino.
The term "halogen", alone or in combination, signifies fluorine, chlorine, bromine or iodine and preferably fluorine, chlorine or bromine.
The term "carbonyl", alone or in combination, signifies the -C(O)- group. The term "oxy", alone or in combination, signifies the -O- group. The term "nitro", alone or in combination signifies the -NOa group. The term "cyano", alone or in combination signifies the group -CN.
The term "pharmaceutically acceptable salts" refers to those salts which retain the biological effectiveness and properties of the free bases or free acids, which are not biologically or otherwise undesirable. The salts are formed with inorganic acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, phosphoric add and the like, preferably hydrochloric add, and organic acids such as acetic acid, propionic add, glycolic acid, pyruvic acid, oxylic acid, maleic acid, malonic acid, succinic add, fumaric
acid, tartaric acid, citric acid, benzoic acid, cinnamic acid, mandelic acid, methanesulfonic acid, ethanesulfonic acid, p-toluenesulfonic acid, salicylic acid, N-acetylcystein and the like. In addition these salts maybe prepared form addition of an inorganic base or an organic base to the free acid. Salts derived from an inorganic base include, but are not limited to, the sodium, potassium, lithium, ammonium, calcium, magnesium salts and the like. Salts derived from organic bases include, but are not limited to salts of primary, secondary, and tertiary amines, substituted amines including naturally occurring substituted amines, cyclic amines and basic ion exchange resins, such as isopropylamine, trimethylamine, diethylamine, triethylamine, tripropylamine, ethanolamine, lysine, arginine, N-ethylpiperidine, piperidine, polymine resins and the like. The compound of formula I can also be present in the form of zwitterions. Particularly preferred pharmaceutically acceptable salts of compounds of formula I are the hydrochloride salts.
The compounds of formula I can also be solvated, e.g. hydrated. The solvation can be effected in the course of the manufacturing process or can take place e.g. .as a consequence of hygroscopic properties of an initially anhydrous compound of formula I (hydration). The term pharmaceutically acceptable salts also includes physiologically acceptable solvates.
"Pharmaceutically acceptable esters" means that compounds of general formula (I) maybe derivatised at functional groups to provide derivatives which are capable of conversion back to the parent compounds in vivo. Examples of such compounds include physiologically acceptable and metabolically labile ester derivatives, such as methoxymethyl esters, methylthiomethyl esters and pivaloyioxymethyl esters. Additionally, any physiologically acceptable equivalents of the compounds of general formula (I), similar to the metabolically labile esters, which are capable of producing the parent compounds of general formula (I) in vivo, are within the scope of this invention.
The compounds of formula I can contain several asymmetric centers and can be present in the form of optically pure enantiomers, mixtures of enantiomers such as, for example, racemates, optically pure diastereioisomers, mixtures of diastereoisomers, diastereoisomeric racemates or mixtures of diastereoisomeric racemates.
Preferred are the compounds of formula I and pharmaceutically acceptable salts thereof, particularly the compounds of formula I.
Further preferred are compounds of formula I, wherein R1 is hydrogen. Also preferred are compounds of formula I, wherein R1 is alkyl, preferably methyl.
Another preferred object of the present invention are the compounds of formula I, wherein R is hydrogen. Further preferred are those compounds according to formula I, wherein R2 is alkyl. Particularly preferred are those compounds of formula I, wherein R2 is methyl.
Also preferred are the compounds of formula I, wherein R3 is hydrogen. Further preferred are those compounds according to formula I, wherein R3 is alkyl.
Another preferred aspect of the present invention are compounds of formula I, wherein R5 is hydrogen.
Particularly preferred are those compounds of formula I, wherein A is C-R10. Further preferred are those compounds of formula I, wherein A is nitrogen.
Preferred are those compounds of formula I, wherein E is C-R9. Further preferred are those compounds of formula I, wherein E is nitrogen.
Another preferred aspect of the present invention are the compounds of formula I, wherein G is C-R8. Also preferred are those compounds of formula I, wherein G is nitrogen.
Preferred are the compounds of formula I, wherein R4 is pheriyl, naphtyl, thiophenyl, pyridyl, quinolyl, piperidyl, morpholyl or thiomorpholyl optionally substituted with one to three, preferably one or two substituents independently selected from alkyl, cycloalkyl, halogen, hydroxy, hydroxyalkyl, alkoxy, alkoxyalkyl, hydroxyalkoxy, alkoxyalkoxy, cyano, trifluoromethyl, trifluoromethoxy, aryl, arylalkyl, aryloxy, heterocyclyl, alkylcarbonylamino, alkoxycarbonylalkoxy and alkyl-SO2-.
Further preferred are compounds of formula I, wherein R4 is phenyl optionally substituted with one to three substituents independently selected from alkyl, cycloalkyl, halogen, hydroxy, hydroxyalkyl, alkoxy, alkoxyalkyl, hydroxyalkoxy, alkoxyalkoxy, cyano, trifluoromethyl, trifluoromethoxy, aryl, arylalkyl, aryloxy, heterocyclyl, alkylcarbonylamino, alkoxycarbonylalkoxy and alkyl-SCV.
Particularly preferred are those compounds of formula I, wherein R4 is phenyl substituted with one to three substituents independently selected from alkyl, halogen and trifluoromethyl.
Preferred are compounds of formula I, wherein R6, R7, R8, R9 and R10 are independently selected from hydrogen, alkyl, halogen and trifluoromethyl.
Particularly preferred are those compounds of formula I, wherein R6 is halogen, alkyl or trifluoromethyl. Especially preferred are those compounds of formula I, wherein R6 is chloro, methyl or trifluoromethyl.
Examples of preferred compounds of formula (I) are:
1. N-[5-(2-Chloro-phenyl)-pyridin-2-yl]-5-fluoro-2-methyl-benzenesulfonamide;
2. 3-Chloro-N-[5-(2-chloro-phenyl)-pyridin-2-yl]-2-methyl-benzenesulfonamide;
3. N- [5-(2,4-Dichloro-phenyl)-pyridin-2-yl] -5-fluoro-2-methyl-benzenesulfonamide;
4. 4a) 3-Chloro-N-[5-(2,4-dichloro-phenyl)-pyridin-2-yl]-2-methyl-
benzenesulfonamide; 4b) 3-Chloro-N-[5-(2-chloro-phenyl)-6-methyl-pyridin-2-yl]-2-methyl-benzenesulfonamide;
5. Biphenyl-4-sulfonic acid [5-(2-chloro-phenyl)-6-methyl-pyridin-2-yl]-amide;
6. 3-Chloro-N-[5-(2-chloro-4-fluoro-phenyl)-pyridin-2-yl]-2-methyl-
benzenesulfonamide;
7. 3-Chloro-N-[5-(3-fluoro-phenyl)-pyridin-2-yl]-2-methyl-benzenesulfonamide;
8. 3-Chloro-N-[5-(2,4-difluoro-phenyl)-pyridin-2-yl]-2-niethyl-benzenesulfonamide;
9. N- [5-(2,4-Difluoro-phenyl)-pyridin-2-yl] -5-fluoro-2-methyl-benzenesulfonamide;
10. 3-Chloro-N-[5-(4-methoxy-phenyl)-pyridin-2-yl]-2-methyl-benzenesulfonamide;
11. 3-Chloro-N- [5-(4-fluoro-phenyl)-pyridin-2-yl]-2-methyl-benzenesulfonamide;
12. 5-Fluoro-N-[5-(4-fluoro-phenyl)-pyridin-2-yl]-2-methyl-benzenesulfonamide;
13. 5-Fluoro-N- [5-(2-methoxy-phenyl)-pyridin-2-yl] -2-methyl-benzenesulfonamide;
14. 3-Chloro-N-[5-(2-flooro-phenyl)-pyridin-2-yi]-2-methyi-benzenesulfonainide;
15. 5-Fluoro-N- [5-(2-fluoro-phenyi)-pyridin-2-yl] -2-methyl-benzenesulfonamide;
16. 2,4-Dichloro-N-[5-(2-chloro-phenyl)-pyridin-2-yi]-6-methyl-benzenesulfonamide;
17. N-[5-(2-Chloro-phenyi)-pyridin-2-yl]-2,5-difluoro-benzenesulfonamide;
18. 3-Chloro-N-[5-(4-methanesulfonyi-phenyl)-pyridin-2-yl]-2-methyi-benzenesulfonamide;
19. 3-Chloro-N-[5-(4-fluoro-phenyl)-6-methyl-pyridin-2-yi]-2-methyl-
benzenesulfonamide;
20. 5-Fluoro-N- [5-(4-fluoro-phenyl)-6-methyl-pyridin-2-yl] -2-methyl-
benzenesulfonamide;
21. 3-Chloro-N-[5-(3-fluoro-phenyl)-6-methyl-pyridin-2-yl]-2-methyl-
benzenesulfonamide;
22. 5-Fluoro-N- [5-(3-fluoro-phenyl)-6-methyl-pyridin-2-yl,] -2-methyl-
benzenesulfonamide;
23. N-[5-(2,4-Dichloro-phenyl)-pyridin-2-yl]-3,4-dimethoxy-benzenesulfonamide;
24. 3,4-Dichloro-N-[5-(2J4-dichloro-phenyl)-pyridin-2-yl] -benzenesulfonamide;
25. N-[5-(2,3-Dichloro-phenyl)-pyridin-2-yl]-2,5-dinuoro-benzenesulfonamide;
26. 3-Chloro-N- [5-(23-dichloro-phenyl)-pyridin-2-yl] -2-methyl-benzenesulfonamide;
27. 3,4-Dichloro-N- [5-(2-chloro-phenyl)-pyridin-2-yl] -benzenesulfonamide;
28. N-[5-(2-Chloro-phenyl)-pyridin-2-yl]-3,4-dimethoxy-benzenesulfonamide;
29. 3-Chloro-N- [5-(2-chloro-phenyl)-pyridin-2-yi] -4-methyl-benzenesulfonamide;
30. 5-Fluoro-N- [5-(4-fluoro-2-methyl-phenyl)-pyridin-2-yl] -2-methyI-
benzenesulfonamide;
31. 3-Chloro-N- [5-(4-fluoro-2-methyl-phenyi)-pyridin-2-yl]-2-methyl-
benzenesulfonamide;
32. 3-Chloro-N- [5-(2-chloro-phenyl)-pyridin-2-yl] -4-methoxy-benzenesulfonamide;
33. 4,5-DichIoro-N- [5-(2-chloro-phenyI)-pyridin-2-yl] -2-fluoro-benzenesulfonamide;
34. 3-Chloro-N- [5-(2,4-dichloro-phenyl)-pyridin-2-yl] -4-methoxy-
benzenesulfonamide;
35. 3-Chloro-N- [5-(2,4-dichloro-phenyl)-pyridin-2-yl] -4-methyl-benzenesulfonainide;
36. Piperidine-1-sulfonic acid [5-(2,4-dichloro-phenyl)-pyridin-2-yl]-aniide;
37. N- [5-(2,3-DichIoro-phenyl)-pyridin-2-yl]-2-trifluoromethyl-benzenesulfonamide;
38. N-[5-(2,3-Dichloro-phenyl)-pyridin-2-yl]-4-fluoro-benzenesulfonamide;
39. N-f5-(2)5-Dicnloro-phenyl)-pyTidin-2-yl]-2,5-difluoro-benzenesulfonamide;
40. N-[5-(2,5-Dichloro-phenyl)-pyridin-2-ylj-5-fluoro-2-methyl-benzenesulfonamide;
41. 3-Chloro-N-[5-(2,5-dichlbro-phenyl)-pyridin-2-yl]-2-methyl-benzenesulfonamide;
42. 5-Huoro-N-[5-(2-fluoro-5-trifluoromethyl-phenyi)-pyridin-2-yl]-2-methyl-
benzenesulfonamide;
43. 3-Chloro-N-[5-(2-fluoro-5-trifluoromethyl-phenyl)-pyridin-2-yl]-2-methyl-
benzenesulfonamide;
44. 3-Chloro-2-methyl-N- [5-(2-trifluoromethyl-phenyl)-pyridin-2-yl] -
benzenesulfonamide;
45. 3-Chloro-4-methyl-N-[5-(2-trifluoromethyl-phenyl)-pyridin-2-yl]-
benzenesulfonamide;
46. 5-Chloro-N-[5-(2,4-dichloro-phenyl)-pyridin-2-yl]-2-methoxy-
benzenesulfonamide;
47. N-{2-Chloro-4-[5-(2,4-dichloro-phenyl)-pyridin-2-ylsulfamoyl]-phenyl}-
acetamide;
48. N-[5-(2)4-Dichloro-phenyl)-pyridin-2-yl]-4-trifluoromethyl-benzenesulfonamide;
49. N-[5-(2,4-DichIoro-phenyl)-pyridin-2-yl]-4-inethysulfonyl-benzenesulfonamide;
50. 3-Chloro-N-[5-(2,3-difluoro-phenyl)-pyridin-2-yl]-4-methyl-benzenesulfonamide;
51. N- [5-(2,3-Difluoro-phenyl)-pyridin-2-yl] -5-fluoro-2-methyl-beiizenestdfonamide;
52. N-[5-(2,4-Bis-trifluoromethyl-phenyl)-pyridin-2-yI]-3-ch]oro-2-methyl-
benzenesulfonamide;
53. N-[5-(2,4-Bis-trifluoromethyl-phenyi)-pyridin-2-yl]-3-chloro-4-methyl-
benzenesulfonamide;
54. 3-Chloro-N-[5-(2,3-difluoro-phenyl)-pyridin-2-yl]-2-methyl-benzenesulfonamide;
55. Piperidine-1-sulfonic acid [5-(2,3-dichloro-phenyl)-pyridin-2-yl]-amide;
56. 5-Chloro-N- [5-(4-fluoro-pbenyl)-6-inethyl-pyridin-2-yi] -2-methoxy-
benzenesulfonamide;
57. N-{2-Chloro-4-[5-(4-fluoro-phenyl)-6-methyl-pyridin-2-ylsulfamoyl]-phenyl}-
acetamide;
58. N-[5-(4-Fluoro-phenyl)-6-methyl-pyridin-2-yl] -4-trifluoromethyl-
benzenesulfonamide;
59. N-[5-(4-Fluoro-phenyl)-6-methyl-pyridin-2-yl]-4-methanesiilfonyl-
benzenesulfonamide;
60. {4- [5- (2,3-Dicbloro-phenyI)-pyridin-2-ylsulfamoyl] -phenoxy} -acetic acid methyl
ester;
61. N-[5-(4-Fluoro-phenyl)-6-methyl-pyridin-2-yl]-4-trifluoromethoxy-
benzenesulfonamide;
62. 3-Chloro-N- [5-(4-fluoro-phenyi)-6-methyirpyridin-2-yi] -4-methoxy-
benzenesulfonamide;
53. 4-Chloro-N-[5-(4-fluoro-phenyl)-6-methyl-pyridin-2-yl] -2,5-dimethyl-benzenesulfonamide;
64. N-[5-(2,3-Dichloro-phenyi)-pyridui-2-)d]-4-(2-liydroxy-ethoxy)-
benzenesulfonamide;
65. N- [5-(2-Chloro-phenyi)-6-methyl-pyridin-2-yl] -4-fluoro-benzenesulfonamide;
66. 3-Chloro-N-[5-(2-chloro-phenyl)-6-methyl-pyridin-2-yl]-4-methyl-
benzenesulfonamide;
67. 4-ChIoro-N- [5-(2-chloro-phenyl)-6-methyl-pyridin-2-yl] -benzenesulfonamide;
68. 2,4-Dichloro-N- [5-(2-chloro-phenyl) -6-methyl-pyridin-2-yl] -6-methyl-
benzenesulfonamide;
69. Piperidine-1-sulfonic acid [5-(2-chloro-phenyl)-6-methyl-pyridin-2-yl]-ainide;
70. N-[5-(2,4-Dichloro-phenyl)-pyridin-2-yl]-4-fluoro-benzenesulfonamide;
71. 4-Chloro-N-[5-(2,4-dichloro-phenyl)-pyridin-2-yl] -2,5-dimethyI-
benzenesulfonamide;
72. N-[5-(2,4-Dichloro-phenyl)-pyridin-2-yI]-214-difluoro-benzenesulfonamide;
73. 2,4-Dichloro-N-[5-(2>4-dichloro-phenyl)-pyridin-2-)d] -5-methyl-
benzenesulfonamide;
74. N-[5-(2,3-Dichloro-phenyl)-pyridin-2-yl]-3-trifluoromethyi-benzenesulfonainide
75. 4-Huoro-N-[5-(4-fluoro-2-methyl-phenyl)-6-methyl-pyridin-2-yl] -
benzenesulfonamide;
76. 3-Chloro-N-[5-(4-fluoro-2-methyl-phenyl)-6-methyl-pyridin-2-yl]-2-methyl-
benzenesulfonamide;
77. 5-Huoro-N-[5-(4-fluoro-2-methyl-phenyl)-6-niethyl-pyridin-2-yl]-2-methyl-
benzenesulfonamide;
'8. 3-Chloro-N-[5-(2,3-dichloro-phenyl)-pyridin-2-yl]-4-methyl-benzenesulfonamide; 9. N-[5-(2,3-Dichloro-phenyl)-pyridin-2-yl]-4-trifluoromethyl-benzenesulfonamide;
80. 3-Chloro-N- [5-(4-fluoro-2-methyl-phenyl)-pyridin-2-ylJ -4-methyl-
benzenesulfonamide;
81. N- [5-(4-Fluoro-2-methyl-phenyl)-pyridui-2-yl] -3-trifluoromethyi-
benzenesulfonamide;
82. N- [5-(4-Fluoro-2-methyi-phenyl)-pyridin-2-yI]-4-trifluoromethyl-
benzenesulfonamide;
83. N- [5-(2-Chloro-phenyi)-pyridin-2-yI] -3-trifluoromethyl-benzenesulfonamide;
84. N-[5-(2-Chloro-phenyl)-pyridin-2-yl]-4-ethyl-benzenesulfonamide;
85. 3-Chloro-N- [5-(2-chloro-phenyl)-pyridin-2-yl] -benzenesulfonamide;
86. 3-Chloro-N-[5-(2,4-dichloro-phenyl)-pyridin-2-yl]-4-fluoro-benzenesiilfonamide;
87. N-[5-(2,4-Dichloro-phenyl)-pyridin-2-yl]-4-ethyl-benzenesulfonamide;
88. N-[5-(2,4-Dichloro-phenyl)-pyridin-2-yl]-3-trifluorometb.yl-benzenesxilfonainide;
89. N-[5-(2-Chloro-phenyl)-6-methyl-pyridin-2-yl]-3-trifluoromethyl-
benzenesulfonamide;
90. N-[5-(2-Chloro-phenyi)-6-methyl-pyridin-2-yl]-4-trifluoromethoxy-
benzenesulfonamide;
91. N-[5-(2-Chloro-phenyl)-pyridin-2-yl]-4-fluoro-benzenesulfonamide;
92. N- [5-(2-Chloro-phenyl)-pyridin-2-yl] -2,4-difluoro-benzenesulfonamide;
93. 4-Chloro-N-[5-(2-chloro-phenyl)-pyridin-2-yl]-2,5-dimethyi-benzenesulfonaniide;
94. 4-Chloro-N- [5-(2-chloro-phenyl)-6-methyl-pyridin-2-yl] -2,5-dimethyi-
benzenesulfonamide;
95. N- [5-(2-Chloro-phenyl)-6-methyl-pyridin-2-yl] -2,4-difluoro-benzenesulfonamide;
96. 3,5-Dichloro-N-[5-(2-chloro-phenyl)-6-methyl-pyridin-2-yl]-benzenesulfonamide;
97. N-[5-(2,4-Dichloro-phenyl)-6-methyl-pyridin-2-yl]-3-trifluoromethyl-
benzenesulfonamide;
98. N-[5-(2,4-Dichloro-phenyl)-6-methyl-pyTidin-2-yl]-4-fluoro-benzenesulfonamide;
99. N- [5-(2,4-Dichloro-phenyl)-6-methyl-pyridin-2-yl]-2,4-difluoro-
benzenesulfonamide;
100. 4-Chloro-N-[5-(2)4-dichloro-phenyl)-6-methyl-pyridin-2-yl]-2,5-diinethyl-
benzenesulfonamide;
101. 2,4-Dichloro-N-[5-(2,4-dichloro-phenyl)-pyridin-2-yl]-6-methyl-
benzenesulfonamide;
102. 3-Chloro-N-[5-(2,4-dichloro-phenyl)-pyridin-2-yl]-benzenesulfonamide;
103. 4-Chloro-N[5-(2,4-dichloro-phenyl)-pyridin-2-yi]-benzenesulfonamide;
104. N-[5-(2-Chloro-phenyl)-6-methyl-pyridin-2-yl]-3-fluoro-benzenesulfonamide;
105. 3-Chloro-N-[5-(2-chloro-phenyI)-6-methyl-pyridin-2-yl]-benzenesulfonamide;
106. 2,4-Dichloro-N-[5-(2-chloro-phenyI)-6-methyl-pyridin-2-yl]-benzenesulfonamide;
107. 2,4-Dichloro-N-[5-(2-chloro-phenyl)-6-methyl-pyridin-2-yl] -5-methyl-
benzenesulfonamide;
108. N-[5-(4-Fluoro-2-methyl-phenyl)-6-methyl-pyridin-2-yl]-3-trifluoromethyl-
benzenesulfonamide;
109. 2,4-Dichloro-N-[5-(4-fluoro-2-methyl-phenyl)-6-methyl-pyridin-2-yl]-6-methyl-
benzenesulfonamide;
110. 3-Chloro-N-[5-(4-fluoro-2-methyl-phenyl)-6-methyl-pyridin-2-yl]-
benzenesulfonamide;
111. 4-ChIoro-N-[5-(4-fluoro-2-methyl-phenyl)-6-methyl-pyridin-2-yl]-
benzenesulfonamide;
112. N-[5-(4-Fluoro-2-methyl-phenyl)-6-methyl-pyridin-2-yl]-4-trifluoromethoxy-
benzenesulfonamide;
113. N-[5-(4-Huoro-2-metliyl-phenyl)-6-methyl-pyridin-2-yl]-3-n?eth.yl-
benzenesulfonamide;
114. 2-ChIoro-N-[5-(4-fluoro-2-methyl-phenyi)-6-inethyl-pyridin-2-yl]-5r
trifluoromethyl-benzenesulfonamide;
115. 4-Fluoro-N-[5-(4-fluoro-2-methyl-phenyl)-6-methyl-pyridin-2-yl]-3-
trifluoromethyl-benzenesulfonamide;
116. N-[5-(2-Chloro-phenyl)-6-methyl-pyridin-2-yi]-3-methyl-benzenesulfonamide;
117. 3-Chloro-N-(2-chloro-phenyl)-6-methyl-pyridin-2-yl]-4-fluoro-
benzenesulfonamide;
118. 2-Chloro-N- [5-(2-chloro-phenyl)-6-methyi-pyridin-2-yl] -5-trifluorometiiyi-
benzenesulfonamide;
119. N- [5-(2-Chloro-phenyi)-6-methyl-pyridin-2-yl] -4-fluoro-3-trifluoromethyl-
benzenesulfonamide;
120. N- [5-(2,3-DicUoro-phenyl)-pyridin-2-yl]-3-fluoro-4-methyl-benzenesulfonamide;
121. N-[5-(2,3-Dichloro-phenyl)-pyridin-2-yl]-3>5-dimethyl-benzenesulfonaniide;
122. N-[5-(5-Fluoro-2-methyi-phenyl)-pyridin-2-yi]-3-trifluoromethyl-
benzenesulfonamide;
123. 4-Fluoro-N-[5-(5-fluoro-2-metliyl-phenyl)-pyridin-2-yl]-benzenesulfonamide;
124. 3-Chloro-N-[5-(5-fluoro-2-methyl-phenyi)-pyridin-2-yl]-2-methyl-
benzenesulfonamide;
125. N-[5-(5-Chloro-2-methyl-phenyl)-pyridin-2-yl]-3-trifluoromethyl-
benzenesulfonamide;
126. N-[5-(5-Chloro-2-methyl-phenyl)-pyridin-2-yl]-4-fluoro-benzenesulfonamide;
127. 3-Chloro-N-[5-(5-chloro-2-methyi-phenyl)-pyridin-2-yl]-2-methyl-
benzenesulfonamide;
128. 3-Chloro-N-[5-(6-chlpro-2-fluoro-3-meth^-phenyl)-pyridin-2-yl]-2-methyl-
benzenesulfonamide;
129. N-[5-(6-Chloro-2-fluoro-3-methyl-phenyl)-pyridiii-2-yi]-3-trifluoromethyl-
benzenesulfonamide;
130. N-[5-(6-Chloro-2-fluoro-3-methyl-phenyl)-pyridin-2-yl]-4-fluoro-
benzenesulfonamide;
131. N-[5-(5-Chloro-2-methyl-phenyl)-6-methyl-pyridin-2-yl]-3-trifluoromethyl-
benzenesulfonamide;
132. N-[5-(5-Chloro-2-methyl-phenyl)-6-methyi-pyridin-2-yl]-4-fluoro-
benzenesulfonamide;
133. 3-Chloro-N-[5-(5-chloro-2-methyi-phenyl)-6-methyI-pyridin-2-yl]-2-methyl-
benzenesulfonamide;
134. N-[5-(6-Chloro-2-fluoro-3-methyl-phenyl)-6-methyl-pyridin-2-yl]-3-
trifluoromethyl-benzenesulfonaniide;
135. N-[5-(6-Chloro-2-fluoro-3-methyl-phenyl)-6-methyi-pyridin-2-yl]-4-fluoro-
benzenesulfonamide;
136. 4-ChIoro-N-[5-(4-fluoro-2-methyl-phenyl)-pyridin-2-yl]-benzenesulfonamide;
137. 3-Chloro-N-[5-(4-fluoro-2-methyl-phenyi)-pyridin-2-yl]-benzenesulfonamide;
138. 2,4-Dichloro-N-[5-(4-fluoro-2-methyl-phenyl)-pyridin-2-yl]-6-methyl-
benzenesulfonamide;
139. 3-ChIoro-N-[5-(2,5-dichloro-phenyl)-6-methyl-pyridin-2-yl]-benzenesulfonamide;
140. N-[5-(2,5-Dichloro-phenyl)-6-methyl-pyridin-2-yl]-4-fluoro-benzenesulfonamide;
141. N-[5-(5-Fluoro-2-methyl-phenyl)-6-methyi-pyridin-2-yl]-3-trifluoromethyl-
benzenesulfonamide;
142. 4-Fluoro-N-[5-(5-fluoro-2-methyl-phenyl)-6-methyl-pyridin-2-yl]-
benzenesulfonamide;
143. 3-Chloro-N-[5-(5-fluoro-2-methyl-phenyi)-6-methyi-pyridin-2-yl]-
benzenesulfonamide;
144. N-[5-(2,5-Dichloro-phenyl)-6-methyl-pyridin-2-yl]-3-trifluoromethyi-
benzenesulfonamide;
145. N- [5-(2-Chloro-4-fluoro-phenyi)-6-methyl-pyridin-2-yi] -3-trifluoromethyl-
benzenesulfonamide;
• 146. N-[5-(2-Chloro-4-fluoro-phenyi)-6-methyl-pyridin-2-yl]-4-fluoro-benzenesulfonamide;
147. 3-Chloro-N-[5-(2-chloro-4-fluoro-phenyl)-6-methyl-pyridin-2-yl]-
benzenesulfonamide;
148. N- [5- (2,3-Dichloro-phenyl) -6-methyi-pyridin-2-yl] -3-trifluoromethyl-
benzenesulfonamide;
149. N- [5-(2,3-Dichloro-phenyl)-6-methyl-pyridin-2-yi] -4-fluoro-benzenesulfonamide;
150. 3-CUoro-N-[5-(2^-dichloro-phenyl)-6-methyi-pyridin-2-yl3-benzenesulfonaniide;
151. 2,4-Dichloro-N-[5-(2,3-dichloro-phenyl)-6-methyl-pyridin-2-yl]-6-methyl-
benzenesulfonamide;
152. N-[5-(2,3-Dichloro-phenyl)-6-methyl-pyridin-2-yi]-3-methyl-benzenesulfonamide;
153. 2,4-Dichloro-N-[5-(2,5-dichloro-phenyl)-6-methyl-pyridin-2-yi]-6-methyl-
benzenesulfonamide;
154. N-[5-(2-Chloro-4-fluoro-phenyl)-6-methyl-pyridin-2-yl]-3-methyl-
benzenesvdfonamide;
155. 2J4-Dicbloro-N-[5-(2-chloro-4-fluoro-phenyl)-6-methyl-pyridin-2-yl]-6-methyl-
benzenesulfonamide;
156. N-[5-(2,4-Bis-trifluoromethyl-phenyl)-pyridin-2-yl]-3-chloro-benzenesulfonainide;
157. N-[5-(2,4-Bis-trifluoromethyl-phenyl)-pyridin-2-yi]-3-methyl-benzenesulfonainide;
158. N-[5-(2,4-Bis-trifluoromethyl-phenyl)-pyridin-2-yi]-4-fluoro-benzenesulfonamide;
159. N-[5-(2,3-Dichloro-phenyl)-6-methyl-pyridin-2-yl]-4-fluoro-3-trifluoromethyi-
benzenesulfonamide;
160. 3-Chloro-N-[5-(2,3-dichloro-phenyl)-6-methyl-pyridin-2-yl]-4-fluoro-
benzenesulfonamide;
161. 3-Chloro-N-[5-(2-fluoro-phenyl)-6-methyl-pyridin-2-yl]-benzenesulfonamide;
162. 4-Fluoro-N-[5-(2-fluoro-phenyl)-6-ftiethyl-pyridin-2-yl]-benzenesulfonamide;
163. 4-Fluoro-N-[5-(2-fluorO'phenyl)-6-methyl-pyridin-2-yl]-3-trifluoromethyl-
benzenesulfonamide;
164. N-[5-(2,4-Bis-trifluoromethyl-phenyl)-pyridin-2-yi]-3-chloro-4-fluoro-
benzenesulfonamide;
165. 2,4-Dichloro-N- [5-(2-fluoro-phenyl)-6-methyi-pyridin-2-yl];-6-methyl-
benzenesulfonamide;
166. N-[5-(2-Huoro-phenyl)-6-methyl-pyridin-2-yl]-3-trifluoromethyl-
benzenesulfonamide;
167. N-[5-(2-Chloro-phenyl)-3,4-dimethyl-pyridin-2-yl]-3-trifluoromethyl-
benzenesulfonamide;
168. 3-Chloro-N-[5-(2-chloro-phenyl)-3,4-dimethyl-pyridin-2-yl]-benzenesulfonamide;
169. N- [5-(2-Chloro-phenyl)-3,4-dimethyl-pyridin-2-yi] -4-fluoro-benzenesulfonamide;
170. N-(2-Methyl-[3,3l]bipyridinyi-6-yl)-3-trifluoromethyl-benzenesulfonamide;
171. 3-Chloro-N-[5-(2-chloro-phenyl)-4-methyl-pyridin-2-yl]-benzenesulfonamide;
172. N-[5-(2-Chloro-phenyl)-4-methyl-pyridin-2-yl]-3-trifluoromethyl-
benzenesulfonamide;
173. 2,4-Dichloro-N-[5-(2-chloro-phenyl)-4-methyl-pyridin-2-yl]-6-methyl-
benzenesulfonamide;
174. 3-Chloro-N-(2-methyi-[3,3']bipyridinyi-6-yl)-benzenesulfonamide;
175. 3-Chloro-N-[5-(4-fluoro-2-methyl-phenyl)-4-methyl-pyridin-2-yl]-
benzenesulfonamide;
176. N-[5-(4-Fluoro-2-methyl-phenyl)-4-methyl-pyridin-2-yl]-3-trifluoromethyi-
benzenesulfonamide; and
177. 2,4-Dichloro-N-[5-(4-fluoro-2-methyl-phenyl)-4-methyl-pyridin-2-yl]-6-methyl-
benzenesulfonamide.
Examples of particularly preferred compounds of formula (I) are: N- [5-(2-Chloro-phenyl)-pyridin-2-yl] -5-fluoro-2-methyl-benzenesulfonamide; 3-Chloro-N- [5-(2-cMoro-phenyl)-pyridin-2-yl] -2-methyl-benzenesulfonamide; 3-Chloro-N- [5- (2,4-dichloro-phenyl) -pyridin-2-yl] -2-methyl-ben2enesulfonamide; 3-Chloro-N-[5-(2-cMoro-phenyl)-6-memyl-pyridin-2-yl]-2-rnethyl-benzenesulfonarnide; 4,5-Dichloro-N-[5-(2-chloro-phenyl)-pyridin-2-yl]-2-fluoro-benzenesulfonamide; 3-Chloro-N-[5-(2,4-dichloro-phenyl)-pyridin-2-yl]-4-rnethyl-benzenesulfonamide; Piperidine-1-sulfonic acid [5-(2,4-dichloro-phenyl)-pyridin-2-yl]-amide; N- [5-(2,3-Dichloro-phenyl)-pyridin-2-yl] -4-fluoro-benzenesulfonamide; 3-CUoro-N-[5-(2-(^oro-phenyl)-6-methyl-pyridin-2-yl]-4-rnethyl-benzenesulfonarnide; 4-Chloro-N-[5-(2-cUoro-phenyl)-6-methyl-pyridin-2-yl]-benzenesulfonamide;
214-Dichloro-N-[5-(2-chloro-phenyl)-6-methyl-pyridin-2-yl]-6-methyl-benzenesulfonamide;
N-[5-(2,4-Dichloro-phenyl)-pyridin-2-yl]-4-fluoro-benzenesulfonamide; N-[5-(2)4-Dichloro-phenyl)-pyridin-2-yl]-2,4-difliloro-benzenesulfonamide;
3 - Chloro-N- [5- (4-fluoro-2-methyl-phenyl) -6-methyl-pyridin-2-yl] -2-methyl-benzenesulfonamide;
3-CUoro-N-[5-(2,3-dichloro-phenyl)-pyridin-2-yl]-4-inethyi-benzenesulfonainide;
3-Chloro-N-[5-(4-fluoro-2-methyi-phenyl)-pyridin-2-yi]-4-methyi-benzenesulfonainide;
N-[5-(4-Fluoro-2-methyI-phenyl)-pyridin-2-yl]-3-trifluoromethyl-beiizenesulfonainide;
N- [ 5- (2,4-Dichloro-phenyl)-pyridin-2-yl] -3-trifluoromethyl-benzenesulfonamide;
N-[5-(2-Chloro-phenyi)-6-methyl-pyridin-2-yl]-3-trifluoromethyl-benzenesulfonamide;
N-[5-(2-Chloro-phenyl)-pyridin-2-yl]-4-fluoro-benzenesulfonamide;
N-[5-(2-Chloro-phenyl)-6-methyl-pyridin-2-yl]-2,4-difluoro-benzenesulfonamide;
N-[5-(2,4-Dichloro-phenyl)-6-methyl-pyridin-2-yi]-2,4-difluoro-benzenesulfonamide;
2,4-Dichloro-N-[5-(2,4-dichloro-phenyi)-pyridin-2-yl]-6-methyl-benzenesulfonainide;
2,4-Dichloro-N-[5-(2-chloro-phenyl)-6-methyl-pyridin-2-yi]-benzenesulfonamide;
N- [5-(4-Fluoro-2-methyl-phenyl)-6-methyl-pyridin-2-yl] -3-trifluoromethyl-benzenesulfonamide;
3-Chloro-N-[5-(4-fluoro-2-methyl-phenyl)-6-methyl-pyridin-2-yi]-benzenesulfonamide; N-[5-(4-Fluoro-2-methyl-phenyl)-6-methyi-pyridin-2-yl]-3-methyi-benzenesiilfonamide; N-[5-(5-Fluoro-2-methyl-phenyi)-pyridin-2-yl]-3-trifluoromethyl-benzenesulfonainide; N-[5-(5-Chloro-2-methyl-phenyl)-pyridin-2-yl]-3-trifluorometh.yi-benzeiiesulfonainide; N- [ 5 - (6-Chloro-2-fluoro-3-methyl-phenyi)-pyridin-2-yl] -4-fluoro-benzenesulfonamide; 3-Chloro-N- [5-(4-fluoro-2-methyl-phenyl)-pyridin-2-yi] -benzenesulfonamide;
2,4-DichIoro-N- [5-(4-fluoro-2-methyl-phenyl)-pyridiii-2-yl] -6-methyI-benzenesulfonamide;
4-Fluoro-N-[5-(5-fluoro-2-methyl-phenyl)-6-methyl-pyridin-2-yl]-benzenesulfonamide;
N- [5-(2-Chloro-4-fluoro-phenyl)-6-methyi-pyridin-2-yl] -3-trifluoromethyl-benzenesulfonamide;
2,4-Dichloro-N-[5-(2,3-dichloro-phenyl)-6-methyl-pyridin-2-yl]-6-methyl-benzenesulfonamide;
2,4-Dichloro-N-[5-(2-chloro-4-fluoro-phenyl)-6-methyl-pyridin-2-yl]-6-methyl-benzenesulfonamide;
N-[5-(2,4-Bis-trifluoromethvl-phenyl)-pyridin-2-yl]-3-chloro-benzenesulfonamide; 3-Chloro-N-[5-(2-chloro-phenyi)-4-methyl-pyridin-2-yl]-benzenesulfonamide; N-[5-(2-CUoro-phenyl)-4-methyi-pyridin-2-yi]-3-trifluoromethyl-benzenesulfonamide; 3-Chloro-N-[5-(4-fluoro-2-methyl-phenyl)-4-methyl-pyridin-2-yl]-benzenesulfonamide;
N-[5-(4-Fluoro-2-methyi-phenyl)-4-methyi-pyridin-2-yl]-3-trifluoromethyl-benzenesulfonamide; and
2,4-Dichloro-N-[5-(4-fluoro-2-methyl-phenyl)-4-methvl-pyridin-2-yl]-6-methyl-benzenesulfonamide.
Processes for the manufacture of compounds of formula I are an object of the invention.
The preparation of compounds of formula I of the present invention may be carried out in sequential or convergent synthetic routes. Syntheses of the invention are shown in the following Schemes. The skills required for carrying out the reaction and purification of the resulting products are known to those in the au. The substituents and indices used in the following description of the processes have the significance given above unless indicated to the contrary.
Compounds of general formula I can be obtained according to scheme 1 from compounds of formula II comprising R1 to R7 substituents and A, E, G definitions according to the above description via a condensation reaction with aryl, heteroaryl or heterocyclyl sulfonyl chlorides, in the presence of a base such as trietylamine or (4-dimetylamino)-pyridine (DMAP) in a solvent such THF, ethanol, methylene chloride DMF or DMSO, or in pyridine as a solvent, with or without the addition of a base such as trietylamine or DMAP, at room temperature or at elevated temperatures, to give compounds of general formula I. Compounds of formula I where R5 equals alkyl can also
be prepared from compounds of formula I where R5 equals H via an alkylation reaction, using, for example, NaH as a base and DMF as solvent, at room temperature or at elevated temperatures.
lternatively, compound of general formula I can be prepared according to scheme 2 from compounds of general formula III in a substitution reaction with an corresponding aryl heteroaryl or heterpcydyl sulphonamide, in the presence of a base such as sodium hydride, NaaCOs or triethyl amine and in a solvent such as THF, DMF or DMSO at room temperature or at elevated temperatures. The reaction can also be carried out under the condition of an UUman-type reaction with, for example Cu(I) chloride, or Cu(I) iodide in a solvent such as dioxane or DMF, in analogy to a method described by S.L. Buchwald (J. Am. Chem. Soc, 2001,7727).
Scheme 2







A further alternative consists of reacting compounds of general formula IV via a metal-catalysed (Pd or Ni) cross-coupling reaction with corresponding organometallic reagent such as (hetero)arylboron, (hetero)arylzink or (hetero)aryltin reagents using Suzuki-,
Stifle- or Negishi-type coupling reactions (for literature: Suzuki, Chem. Rev., 1995,95, 2475; Stille, Angew. Chem. IEE, 1986,25,508; Negishi, Ace. Chem: Res., 1982,15,340).
Intermediated II, III and IV are either commercial available, known in the literature or can be prepared by applying a sequence of standard reactions known in the art and outlined in scheme 4. Thus, starting from appropriate 2-pyridones of formula V, which are either known in the literature or can be prepared according to standard procedures, subsequent halogenation with POC13.PC13 or POBrs gives rise to the corresponding 2-chloro or 2-bromo pyridines of formula VI. The iodo derivatives can be obtained from the chloro or bromo derivatives via halogen exchange with Nal (for general reaction of this type: R.C. Corcoran, Tetrahedron Lett. 1990, p6757). Subsequent reaction with alkyl amines or ammonia, either applied in access, without solvent, or in equimolar amounts, in a suited solvent such as ethanol, water, DMF or THF, gives rise to compounds of formula VEL The reaction can also be performed in an autoclave at elevated pressure in analogy to published procedures (for an example: T. Haga, Heterocyles, 22, pl!7).

Compounds of formula II can then be be prepared from VU via a metal-catalysed (Pd or Ni) cross-coupling reaction with corresponding organometallic reagent such as (hetero)arylboron, (hetero)arylzink or (hetero)aryltin reagents using Suzuki-, Stille- or Negishi-type coupling reactions as descibed above. The amino group can optionally be protected with standard protecting groups such as BOC or pivaloyl prior to performing the cross-coupling reaction. Compounds of formula III are obtained from compounds of formula VIII (prepared from V via metal-catalysed cross-coupling as for II) by an halogenation reaction (as for the preparation of VI). Compounds of formula IV can be prepared from VI via a nudeophilic substitution reaction with a corresponding aryl, heteroayryl or heterocycylyl sulfonamide in a solvent such as DMSO or DMF in the
presence of a base such as sodium hydride, at room temperature or at elevated temperature. The sulfonamides used in this step are either commercial, known in the literature or can be obtained by standard procedures known in the art. They can also first be converted into their sodium or potassium and these salts can then be used in the reaction, a procedure which does not require the addition of further base. Alternatively, IV can be obtained from VII by reacting with the corresponding aryl, heteroaryi or heterocyclyl sulfonyl chlorides as described above.
A preferred process for the preparation of a compound of formula I, wherein R1 to R7, A, E and G are defined as before comprises the reaction of a compound according to formula
in the presence of a compound according to formula

wherein R1 to R7, A, E and G are defined as before. Particularly preferred is the above process in the presence of a base such as trietylamine or (4-dimetylamino)-pyridine (DMAP) in a solvent such THF, ethanol, methylene chloride DMF or DMSO, or in pyridine as a solvent, with or without the addition of a base such as trietylamine or DMAP, at room temperature or at elevated temperatures.
Preferred intermediates are:
5-(2-chloro-phenyl)-pyridin-2-ylamine;
5-(2,4-dichloro-phenyl)-pyridin-2-ylamine;
5-(2-chloro-phenyl)-6-methyl-pyridin-2-ylamine;
5- (2-chloro-4-fluoro-phenyl)-pyridin-2-ylamine;
5-(3-fluoro-phenyl)- pyridin-2-yiamine;
5-(2,4-difluoro-phenyl)-pyridin-2-ylamine;
5-(4-methoxy-phenyi)-pyridin-2-yiamine;
5-(4-fluoro-phenyi)-pyridin-2-ylamine;
5-(2-methoxy-phenyi)-pyridin-2-ylamine;
5-(2-fluoro-phenyl)-pyridin-2-ylamine;
5-(2-chloro-phenyl)-pyridin-2-yIaniine;
5-(4-methanesulfonyI-phenyl)-pyridin-2-ylaniine;
5-(4-fluoro-phenyi)-6-methyl-pyridin-2-ylamine;
5-(3-fluoro-phenyl)-6-methyl-pyridin-2-ylamine;
5-(2,3-dichloro-phenyl)-pyridin-2-ylamine;
5-(4-fluoro-2-methyl-phenyl)-pyridin-2-yiamine;
5-(2,5-dichloro-phenyl)-pyridin-2-yIamine;
5-(2-fluoro-5-trifluoromethyl-phenyl)-pyridin-2-ylamine;
5-(2-trifluoromethyi-phenyl)-pyridin-2-ylamine;
5-(2,3-difluoro-phenyl)-pyridin-2-ylamine;
5-(2,4-bis-trifluoromethyl-phenyl)-pyridin-2-yiamine;
5-(4-fluoro-2-methyi-phenyi)-6.-methyl-pyridin-2-ylamine;
5-(2,4-chloro-phenyi)-6-methyl-pyridin-2-ylamine;
5-(5-fluoro-2-methyl-phenyl)-pyridin-2-yiamine;
5-(5-chloro-2-methyl-phenyl)-pyridin-2-ylamine;
5-(6-Chloro-2-fluoro-3-methyl-phenyi)-pyridin-2-ylamine;
5-(5-Chloro-2-methyl-phenyI)-6-methyl-pyridin-2-ylaniine;
5-(6-Chloro-2-fluoro-3-methyl-phenyi)-6-methyl-pyridin-2-ylamine;
5-(2,5-Dichloro-phenyl)-6-inethyl-pyridin-2-ylamine;
5-(5-Fluoro-2-methyi-phenyl)-6-methyl-pyridin-2-ylamine;
5-(2-Chloro-4-fluoro-phenyl)-6-methyl-pyridin-2-yiamine;
5-(2,3-Dichloro-phenyl)-6-methyl-pyridin-2-ylaniine;
5-(2-Fluoro-phenyl)-6-metiiyl-pyridin-2-ylamine;
5- (2- Chloro-phenyi)-3,4-dimethyi-pyridin-2-ylamine;
2-Methyl-[3,3']bipyridinyl-6-ylamine;
5-(2-Chloro-phenyl)-4-methyl-pyridin-2-ylamineand
5-(4-Pluoro-2-methyl-jihenyl)-4-methyl-pyridin-2-ylamine.
The compounds of formula I described above for use as therapeutically active substance are a further object of the invention.
Also an object of the present invention are compounds as decribed above for the preparation of medicaments for the prophylaxis and therapy of illnesses which are caused by disorders associated with the enzyme llbeta-hydroxysteroid dehydrogenasel (llbHSDl).
Likewise an object of the invention are pharmaceutical compositions comprising a compound of the formula I as described above and a therapeutically inert carrier.
A further preferred embodiment of the present invention is the use of a compound of the formula I as described above for the preparation of medicaments for the treatment and prophylaxis of diabetes, obesity, eating disorders, dyslipidemiae and hypertension.
Particularly preferred is the use of a compound according to formula I as described above for the preparation of medicaments for the treatment and prophylaxis of diabetes Type II.
A further object of the present invention comprises a compound according to formula I as described above, when manufactured according to any one of the described processes.
Also an object of the invention is a method for the treatment and prophylaxis of diabetes, obesity, eating disorders, dyslipidemiae and hypertension, which method comprises administering an effective amount of a compound of formula I as described above.
Particularly preferred is a method for the treatment and prophylaxis of diabetes Type II, which method comprises administering an effective amount of a compound according to formula I as described above.
Assay Procedures Transient expression and partial Purification:
The cDNA encoding the human llbeta-HSDl protein was cloned into the expression vector pcDNA3 (Stratagene). This construct (for details see Alex Odermatt et al.; J Biol Chem.,1999, Vol. 274, Issue 40, 28762-28770) was used to transiently express the protein in HEK293 cells (ATCC number: CRL-1573, described in Graham, F.L., Smiley, J., Russell, W.C., Nairn, R.; (1977)) using lipofectamine. 48h after transfection cells were washed twice with ice-cold PBS (Phsophate buffered Saline). To 1 volume of cell suspension in PBS 2 volumes of ice-cold lysis buffer (50mM Trisj pH7.5; ImM EDTA; lOOmM NaCl) were added. The cells were lysed by Potter-homogenization (20 strokes). The resulting homogenate was sonicated wit a tip sonicator (10% output; 2 x 30 sec.) and cleared by a low speed centrifugation (lOmin x 9000g; 4°C). The microsomal fraction was collected by a high speed centrifugation (60 min x 110'OOOg). The resulting pellet was resuspended in storage buffer (20mM Tris pH 7.5; 1 mM EDTA; 10% Glycerol) and the centrifugation was repeated. The resulting pellet containing the microsomal fraction was again taken up into storage buffer and aliquots were kept frozen in liquid Nitrogen until use.
Generation of stable cell lines expressing llbeta-HSDl:
The same construct used for transient expression of human llbeta-HSDl was also used to establish cell lines stably expressing the protein. Briefly, (HEK293) cells were transfected with llbeta-HSDl construct using the lipofectamine reagent (Gibco BRL) according to the manufacturer's instruction. Two days after transfection, geneticin selection (0.8 mg/ml) was initiated and several stable clones were isolated. One clone was further used for pharmacological characterization.
Microsome Assay
Microsomes isolated from HEK293 cells transiently expressing human llbeta-HSDl (for details see above) were incubated in assay buffer (100 mM NaCl; ImM EDTA; ImM EGTA; ImM MgCl; 250 mM Sucrose; 20 mM Tris pH 7.4; Cortisone 50-200nM and NADPH ImM) together with different concentrations of test substances. After 60 min. of incubation at 37°C the assay was stopped by heating to 80°C (5 min.) and by addition of the inhibitor Carbenoxolone (1 uM). The amount of Cortisol produced in this assay was determined using a commercially available, ELISA-based Cortisol-detection kit

(Distributed by Assay Design, Inc.). Inhibitors were characterized by there IC50 values, e.g. the concentration at which the production of cortisol was 50% reduced.
In this test preferred compounds as described above have IC50 values below 1000 nM; more preferred compounds have IC50 values below 100 nM. Most preferred compounds have IC50 values below lOnM.
Cellular Assay
To measure the effect of inhibitors in intact cells HEK293 cells stably expressing human llbeta-HSDl (see above) were cultivated in 96 well plates in DMEM. First inhibitors and 60 min later Cortisone was added to the cells. After 60 min of incubation at 37°C in a 5% CO2 atmosphere part of the medium was removed and the conversion from Cortisone to Cortisol was measured using a commercially available ELISA kit (Distributed by Assay Design, Inc.).
Results obtained in the microsome assay using representative compounds of the invention as the test compounds are shown hi the following table:

Compounds as described above have ICso values below 1000 nM; preferred compounds have ICso values below 100 nM. More preferred compounds have ICso values below 10 nM. These results have been obtained by using the foregoing test.
The compounds of formula I and their pharmaceutically acceptable salts and esters can be used as medicaments (e.g. in the form of pharmaceutical preparations). The pharmaceutical preparations can be administered internally, such as orally (e.g. in the form of tablets, coated tablets, drage'es, hard and soft gelatin capsules, solutions, emulsions or suspensions), nasally (e.g. in the form of nasal sprays) or rectally (e.g. in the form of suppositories). However, the administration can also be effected parentally, such as intramuscularly or intravenously (e.g. in the form of injection solutions).
The compounds of formula I and their pharmaceutically acceptable salts and esters can be processed with pharmaceutically inert, inorganic or organic adjuvants for the production of tablets, coated tablets, drage'es and hard gelatin capsules. Lactose, corn starch or derivatives thereof, talc, stearic acid or its salts etc. can be used, for example, as such adjuvants for tablets, dragees and hard gelatin capsules.
Suitable adjuvants for soft gelatin capsules, are, for example, vegetable oils, waxes, fats, semi-solid substances and liquid polyols, etc.
Suitable adjuvants for the production of solutions and syrups are, for example, water, polyols, saccharose, invert sugar, glucose, etc.
Suitable adjuvants for injection solutions are, for example, water, alcohols, polyols, glycerol, vegetable oils, etc.
Suitable adjuvants for suppositories are, for example, natural or hardened oils, waxes, fats, semi-solid or liquid polyols, etc.
Moreover, the pharmaceutical preparations can contain preservatives, solubilizers, viscosity-increasing substances, stabilizers, wetting agents, emulsifiers, sweeteners, colorants, flavorants, salts for varying the osmotic pressure, buffers, masking agents or antioxidants. They can also contain still other therapeutically valuable substances.
In accordance with the invention the compounds of formula I and their pharmaceutically acceptable salts can be used for the prophylaxis and treatment of arthritis, cardiovascular diseases, diabetes, renal failure and particularly eating disorders and obesity. The dosage can vary in wide limits and will, of course, be fitted to the individual requirements in each particular case. In general, in the case of oral idministration a daily dosage of about 0.1 mg to 20 mg per kg body weight, preferably ibout 0.5 mg to 4 mg per kg body weight (e.g. about 300 mg per person), divided into
preferably 1-3 individual doses, which can consist, for example, of the same amounts, should be appropriate. It will, however, be clear that the upper limit given above can be exceeded when this is shown to be indicated.
The invention is illustrated hereinafter by Examples, which have no limiting character.
Examples
Example 1
a) A solution of 0.2 g (0.98 mmol) of 5-(2-chloro-phenyi)-pyridin-2-ylamine and 0.23 g of 5-fluoro-2-methyl-benzenesulfonyl chloride (1.1 mmol) in pyridine (10 ml) was stirred at RT until completion of reaction according to HPLC analysis (48 h): After concentration in vacuo the residue was taken up in EtOAc, the solution washed withl N aqueous HC1, saturated brine then dried over sqdium sulphate and concentrated in vacuo. The precipitate was collected by filtration and dried in a high vacuum to give 0.21 g (57%) of N-[5-(2-chloro-phenyl)-pyridin-2-yl]-5-fluoro-2-methyl-benzenesulfonamide as an off-white crystalline solid. ISN mass spectrum, m/e: 375.2 (M-l calculated for : 375).
Preparation of the starting material:
b) A suspension of 70 mg (0.06 mmol) of tetrakis(triphenylphosphine) palladium(O) in benzene (4 ml) was treated at RT under an argon atmosphere successively with 0.35 g (2 mmol) of 2-amino-5-bromo-pyridine, 2.2 ml (4.4 mmol) of 2 M aqueous NaaCOs solution, 0.34 g (2.2 mmol) of 2-chlorophenylboronic acid in ethanol (1 ml) and heated to reflux for 24 h. The reaction mixture was cooled and partitioned between EtOAc and water. The layers were separated, the organic layer dried over sodium sulphate and concentrated in vacuo. The residue was applied to a silica gel column with EtOAc as eluent. Combination of the purified fractions and concentration in vacuo gave 0.4 g (98%)
of the desired 5-(2-dJoro-phenyl)-pyridin-2-ylainine as white crystalline solid. ISP mass spectrum, rn/e: 205.1 (M+l calculated for CiiH9aN2:205).
Example 2
In analogy to example 1, on reaction of 5-(2-chloro-phenyl)-pyridin-2-ylamine with 3-chloro-2-methyl-benzenesulfonyl chloride there was obtained: 3-chloro-N-[5-(2-chloro-phenyl)-pyridin-2-yl]-2-inethyl-benzenesulfonamide as an off-white solid. ISN mass spectrum, m/e: 391 (M-l calculated for Ci8HuCl2N2O2S: 391).
Examples
a) In analogy to example 1, on reaction of 5-(2>4-dichloro-phenyl)*-pyridin-2-ylamine with
5-fluoro-2-methyl-benzenesulfonyi chloride there was obtained: N-[5-(2,4-dichloro-
phenyl)-pyridin-2-yl]-5-fluoro-2-methyi-benzenesulfonaniide as an off-white solid. ISN
mass spectrum, m/e: 409 (M-l calculated for Clg Hi3Cl2FN2O2 S: 409).
Preparation of the starting material:
b) In analogy to example lb), on reaction of 2-amino-5-bromo-pyridine with 2,4-
dichlorophenyiboronic acid there was obtained: 5-(2,4-dichloro-phenyl)-pyridin-2-
ylamine as a white crystalline solid which was used without further purification in the
subsequent reaction step.
Example 4a
In analogy to example 1, on reaction of 5-(2,4-dichloro-phenyl)-pyridin-2-ylamine with 3-chloro-2-methyl-benzenesulfonyl chloride there was obtained: 3-Chloro-N-[5-(2,4-dichloro-phenyl)-pyridin-2-yl]-2-methyl-benzenesulfonamide as an off-white solid. ISN mass spectrum, m/e: 425 (M-l calculated for CjgH^Cy^C^S: 425).
Example 4b
a) In analogy to example 1, on reaction of 5-(2-chloro-phenyl)-6-methyl-pyridin-2~
ylamine with 3-chloro-2-methyl-benzenesulfonyl chloride there was obtained: 3-Chloro-
N-[5-(2-crJoro-pbenyl)-6-rnethyl-pyridin-2-yl]-2-methyl-benzenesulfonamide as a white
solid. ISN mass spectrum, m/e: 405.1 (M-l calculated for Ci9 HisClj^OaS: 405).
Preparation of the starting material:
b) In analogy to example Ib), on reaction of 5-bromo-6-methyl-pyridin-2-ylamine with 2-
chlorbphenylboronic acid there was obtained: 5-(2-chloro-phenyl)-6-methyl-pyridin-2-
ylamine as a white crystalline solid, ISP mass spectrum, m/e: 219.2 (M+1 calculated for Cu
2: 219).
Example 5
In analogy to example 1, on reaction of 5-(2-chloro-phenyl)-6-methyl-pyridin-2-ylamine with biphenyi-4-sulfonyl chloride there was obtained: Biphenyl-4-sulfonic acid (5-(2-chloro-phenyl)-6-methyl-pyridin-2-yi]-amide as a white foam. ISN mass spectrum, m/e: 433.2 (M-l calculated for CiiH^ONaOzS: 433).
Example 6
a) In analogy to example 1, on reaction of 5-(2-chloro-4-fluoro-phenyl)-pyridm-2-ylamine with 3-chloio-2-methyl-benzenesulfonyl chloride there was obtained: 3-Chloro-N-[5>-(2-chloro-4-fluoro-phenyl)-pyridin-2-yl]-2-meihyl-benzenesulfonamideasan imorphous white solid. ISN mass spectrum, m/e: 409 (M-l calculated for Ci8 Hn 312FN202S: 409).
'reparation of the starting material:
0 In analogy to example Ib), on reaction of 5-bromo-pyridin-2-ylamine with 2-chloro-4-uoro-phenylboronic acid there was obtained: 5-(2-chloro-4-fluoro-phenyl)- pyridin-2-lamine as a white crystalline solid which was used without further purification in the next :action step.
Example 7
a) In analogy to example 1, on reaction of 5-(3-fluoro-phenyi)- pyridin-2-ylamine with 3-
chloro-2-methyl-benzenesulfonyl chloride there was obtained: 3-Chloro-N-[5-(3-fluoro-
phenyl)-pyridin-2-yl]-2-methyl-benzenesulfonamide as a crystalline white solid, ISN mass
spectrum, m/e: 375.2 (M-l calculated for QgHuQK^ChS: 375).
Preparation of the starting material:
b) In analogy to example Ib), on reaction of 5-bromo-pyridin-2-ylamine with 3-fluro-
phenylboronic acid there was obtained: 5-(3-fluoro-phenyl)- pyridin-2-ylamine as a white
crystalline solid which was used without further purification in the next reaction step.
Example 8
a) In analogy to example 1, on reaction of 5-(2,4-difluoro-phenyl)-pyridin-2-ylamine with
3-chloro-2-methyl-benzenesulfonyl chloride there was obtained: 3-Chloro-N- [5-(2,4-
difluoro-phenyl)-pyridin-2-yl]-2-methyl-benzenesulfonamide as a crystalline white solid.
ISN mass spectrum, m/e: 392.9 (M-1 calculated for CigHi3ClF2N2O2S: 392).
Preparation of the starting material:
b) In analogy to example Ib), on reaction of 5-bromo-pyridin-2-ylamine with 2,4-
difluoro-phenylboronic acid there was obtained: 5-(2,4-difluoro-phenyl)-pyridin-2-
ylamuie as a white crystalline which was used without further purification in the next
reaction step.
Example 9
In analogy to example 1, on reaction of 5-(2,4-oUfluoro-phenyl)-pyridin-2-ylamine with 5-fluoro-2-methyl-benzenesulfbnyl chloride there was obtained: N- [5-(2,4-Difluoro-phenyl)-pyridin-2-yl]-5-fiuoro-2-methyl-benzenesulfonamide as a crystalline white solid. ISN mass spectrum, m/e: 377.1 (M-l calculated for CuRiA^C^S: 377).
Example 10
a) In analogy to example 1, on reaction of 5-(4-methoxy-phenyl)-pyridin-2-ylaniine with
3-chloro-2-methyl-benzenesulfonyl chloride there was obtained: 3-Chloro-N-[5-(4-
methoxy-phenyl)-pyridin-2-yl]-2-methyi-benzenesulfonamide as a crystalline white solid.
ISN mass spectrum, m/e: 387.1 (M-l calculated for Ci9Hi7ClN2O2S: 387).
Preparation of the starting material:
b) In analogy to example Ib), on reaction of 5-bromo-pyridin-2-ylamine with 4-methoxy-
phenylboronic acid there was obtained: 5-(4-methoxy-phenyl)-pyridin-2-ylamine as a
beige crystalline solid which was used without further purification in the next reaction
step.
Example 11
a) In analogy to example 1, on reaction of 5-(4-fluoro-phenyl)-pyridin-2-ylamine with 3-
chloro-2-methyl-benzenesulfonyl chloride there was obtained: 3-Chloro-N-[5-(4-fluoro-
phenyl)-pyridin-2-yl]-2-methyl-benzenesulfonamide as a crystalline white solid. ISN mass
spectrum, m/e: 375.2 (M-l calculated for CigHuClF^C^S: 375).
Preparation of the starting material:
b) In analogy to example Ib), on reaction of 5-bromo-pyridin-2-ylamine with 4-fluoro-
phenylboronic acid there was obtained: 5-(4-fluoro-phenyl)-pyridin-2-ylamine as a brown
crystalline solid which was used without further purification in the next reaction step.
Example 12
In analogy to example 1, on reaction of 5-(4-fluoro-phenyl)-pyridin-2-ylamine with 5-fluoro-2-methyl-benzenesulfonyl chloride there was obtained: 3-Chloro-N-[5-(4-fluoro-phenyl)-pyridin-2-yl]-2-methyl-benzenesulfonamide as a crystalline off-white solid. ISN mass spectrum, m/e: 359 (M-l calculated for QsHniy^OjS: 359).
Example 13

a) In analogy to example 1, on reaction of 5-(2-methoxy-phenyl)-pyridin-2-ylamine with
5-fluoro-2-methyl-benzenesulfonyl chloride there was obtained: 5-Fluoro-N-[5-(2-
methoxy-phenyl)-pyridin-2-yl]-2-methyl-benzenesulfonamide as a crystalline white solid.
ISN mass spectrum, m/e: 371.1 (M-l calculated for C^H^FNaC^S: 371).
Preparation of the starting material:
b) In analogy to example Ib), on reaction of 5-bromo-pyridin-2-ylamine with 2-methoxy-
phenylboronic acid there was obtained: 5-(2-methoxy-phenyl)-pyridin-2-ylamine as
yellow oil which was used without further purification in the next reaction step.
Example 14
a) In analogy to example 1, on reaction of 5-(2-fluoro-phenyl)-pyridin-2-ylamine with 3-
chloro-2-methyl-benzenesulfonyl chloride there was obtained: 3-Chloro-N-[5-(2-fluoro-
phenyl)-pyridin-2-yl]-2-methyl-benzenesulfonamide as a crystalline white solid. ISN mass
spectrum, m/e: 3752 (M-l calculated for Ci8Hi4ClFN2O2S: 375).
Preparation of the starting material:
b) In analogy to example Ib), on reaction of 5-bromo-pyridin-2-ylamine with 2-fluoro-
phenylboronic acid there was obtained: 5-(2-fluoro-phenyl)-pyridin-2-ylamine as yellow
oil which was used without further purification in the next reaction: step.
Example 15
In analogy to example 1, on reaction of 5-(2-fluoro-phenyl)-pyridin-2-ylamine with 5-fluoro-2-methyl-benzenesulfbnyl chloride there was obtained: 5-Fluoro-N-[5-(2-fluoro-phenyl)-pyridin-2-yl]-2-rnethyl-benzenesulfonarnide as amorphous white solid. ISN mass spectrum, m/e: 359 (M-l calculated for QeHuPa^O^: 359).
Example 16
In analogy to example 1, on reaction of 5-(2-chloro-phenyl)-pyridin-2-ylaminewith 2,4-dichloro-6-methyl-benzenesulfonyl chloride there was obtained: 2,4-Dichloro-N-[5-(2-chloro-phenyl)-pyridin-2-yl]-6-methyl-benzenesulfonamide as a colourless crystalline solid. ISP mass spectrum, m/e: 425 (M-l calculated for CisHuCUNzOzS: 425).
Example 17
In analogy to example 1, on reaction of 5-(2-chloro-phenyl)-pyridin-2-ylamine with 2,5-difluoro-benzenesulfonyl chloride there was obtained: N-[5-(2-chloro-phenyl)-pyridin-2-yl]-2,5-difluoro-benzenesulfonamide as a white crystalline solid. ISN mass spectrum, m/e: 379 (M-l calculated for CiyHnClF^C^S: 379).
Example 18
a) In analogy to example 1, on reaction of 5-(4-methanesulfonyl-phenyl)-pyridin-2-ylamine with 3-chloro-2-methyl-benzenesulfonyl chloride there was obtained: 3-Chloro-N- [5-(4-methanesulfonyl-phenyl)-pyridin-2-yl] -2-methyl-benzenesulfonamide as an amorphous white solid. ISN mass spectrum, m/e: 435.1 (M-l calculated for 2: 435).
Preparation of the starting material:
b) In analogy to example Ib), on reaction of 5-bromo-pyridin-2-ylamine with 4-methanesulfonyl-phenylboronic acid there was obtained: 5-(4-methanesulfonyl-phenyl)-pyridin-2-ylamine as a white crystalline solid which was used without further purification in the next reaction step.
Example 19
a) In analogy to example 1, on reaction of 5-(4-fluoro-phenyl)-6-methyl-pyridin-2-ylamine with 3-chloro-2-methyl-benzenesulfonyi chloride there was obtained: 3-Chloro-N-[5-(4-fluoro-phenyl)-6-methyl-pyridin-2-yl]-2-methyl-benzenesulfonamide as a yellow foam. ISN mass spectrum, m/e: 389 (M-l calculated for Ci9Hi6ClFN2O2S: 389).
Preparation of the starting material:
b) In analogy to example lb), on reaction of 5-bromo-6-methyl-pyridin-2-ylamine with 4-fluoro-phenylboronic acid there was obtained: 5-(4-fluoro-phenyl)-6-methyl-pyridin-2-ylamine as a yellow crystalline solid which was used without further purification in the next reaction step.
Example 20
In analogy to example 1, on reaction of 5-(4-fluoro-phenyl)-6-methyl-pyridm-2-ylarnine with 5-fluoro-2-methyl-benzenesulfonyl chloride there was obtained: 5-Fluoro-N-[5-(4-fluoro-phenyl)-6-methyl-pyridin-2-yl]-2-meth)d-benzenesulfonamide as a light-yellow foam. ISN mass spectrum, m/e: 373.1 (M-l calculated for C^H^^C^S: 373).
Example 21
a) In analogy to example 1, on reaction of 5-(3-fluoro-phenyl)-6-rnethyl-pyridin-2-
ylamine with 3-chloro-2-methyl-benzenesulfonyl chloride there was obtained: 3-Chloro-
N-[5-(3-fluoro-phenyl)-6-methyl-pyridin-2-yl]-2-methyl-benzenesulfonamide as a yellow
foam. ISN mass spectrum, m/e: 389.1(M-1 calculated for CigHigCM^C^S: 389).
Preparation of the starting material:
b) In analogy to example lb), on reaction of 5-bromo-6-methyl-pyridin-2-ylamine with 3-
fluoro-phenylbororuc acid there was obtained: 5-(3-fluoro-phenyl)-6-rnethyl-pyridin-2-
ylamine as a white crystalline solid which was used without further purification in the next
reaction step.
Example 22
In analogy to example 1, on reaction of 5-(3-fluoro-phenyl)-6-methyl-pyridin-2-ylamine with 5-fLuoro-2-methyl-benzenesulfonyl chloride there was obtained: 5-Fluoro-N-[5-(3-fluoro-phenyl)-6-methyl-pyridin-2-yl]-2-methyl-benzenesulfonamide as a light-yellow foam. ISN mass spectrum, m/e: 373.1(M-1 calculated for C^HieFzNaC^S: 373).
Example 23
In analogy to example 1, on reaction of 5-(2,4-dichloro-phenyl)-pyridin-2-ylamine with 3,4-dimethyoxy-benzenesulfonyl chloride there was obtained: N-[5-(2,4-Dichloro-phenyl)-pyridin-2-yl]-3J4-dimethoxy-benzenesulfonamide as a light-yellow foam. ISN mass spectrum, m/e: 437.1(M-1 calculated for Ci9Hi6Cl2N2O4S: 437).
Example 24
In analogy to example 1, on reaction of 5-(2)4-dichloro-phenyl)-pyridin-2-ylamine with 3,4-dichloro-benzenesulfonyl chloride there was obtained: 3,4-Dichloro-N-[5-(2,4-dichloro-phenyl)-pyridin-2-yl]-benzenesulfonamide as an crystalline white solid. ISN mass spectrum, m/e: 446.9 (M-l calculated for QyHujCLiN^S: 447).
Example 25
a) In analogy to example 1, on reaction of 5-(2,3- Preparation of the starting material:
b) In analogy to example lb), on reaction of 5-bromo -pyridin-2-ylamine with 2,3-dichloro-phenylboronic acid there was obtained: 5-(2,3-dichloro-phenyl)-pyridin-2-ylamine as an of- white crystalline solid. El mass spectrum, m/e: 239.1 (M calculated for CnH8Cl2N2: 239).
Example 26
In analogy to example 1, on reaction of 5-(2,3-dichloro-phenyl)-pyridin-2-ylamine with 3-chloro-2-methyl-benzenesulfonyl chloride there was obtained: 3-Chloro-N-[5-(2,3-dichloro-phenyl)-pyridin-2-yl]-2-methyl-benzenesulfonamide as a white solid. ISN mass spectrum, m/e: 427 (M-l calculated for Ci8Hi3Cl3N2O2S: 427).
Example27
In analogy to example 1, on reaction of 5-(2-chloro-phenyl)-pyridin-2-ylamine with 3,4-dichloro-benzenesulfonyl chloride there was obtained: 3,4-dichloro-N-[5-(2-chloro-phenyl)-pyridin-2-yl]-benzenesulfonamide as a white crystalline solid. ISN mass spectmm, m/e: 411 (M-l calculated for C17HuCl3N2O2S: 411).
Example 28
In analogy to example 1, on reaction of 5-(2-chloro-phenyl)-pyridin-2-ylamine with 3,4dimethoxy-benzenesulfonyl chloride there was obtained: N-[5-(2-Chloro-phenyl)-pyridin-2-yl]-3,4-dimethoxy-benzenesulfonamide as a white crystalline solid. ISN mass spectrum, m/e: 403.2 (M-1 calculated for QjHiTCIN^^: 403).
Example 29
In analogy to example 1, on reaction of 5-(2-chloro-phenyl)-pyndin-2-ylamine with 3-chloro-4-methyl-benzenesulfonyl chloride there was obtained: 3-Chloro-N-[5-(2-chloro-phenyl)-pyridin-2-yl]-4-methyl-benzenesulfonamide as a white crystalline solid. ISN mass spectrum, m/e: 391 (M+l calculated for QgHuCyNiCUS: 391).
Example 30
a) In analogy to example 1, on reaction of 5-(4-fluoro-2-methyl-phenyl)-pyridin-2-ylamine with 5-fluoro-2-methyl-benzenesulfbnyl chloride there was obtained: 5-Fluoro-
§
N-[5-(4-fluoro-2-meth)d-phenyl)-pyridin-2-yl]-2-methyl-benzenesulfonamide as a light-yellow solid. ISN mass spectrum, m/e: 373 (M-l calculated for CuHieFaNjChS: 373).
Preparation of the starting material:
b) In analogy to example Ib), on reaction of 5-bromo -pyridin-2-ylamine with 4-fluoro-2-tnethyl-phenylboronic acid there was obtained: 5-(4-fluoro-2-methyl-phenyl)-pyridin-2-
ylamine as a white solid. ISP mass spectrum, m/e: 203.1 (M+l calculated for Ci2HnFN2: 203).
Example 31
In analogy to example 1, on reaction of 5-(4-fluoro-2-methyl-phenyl)-pyridin-2-yiamine with 3-chloro-2-methyl-benzenesulfonyl chloride there was obtained: 3-Chloro-N-[5-(4-fluoro-2-methyl-phenyl)-pyridin-2-yl]-2-methyl-benzenesulfonamide as a light-yellow solid. ISN mass spectrum, m/e: 389.1(M-1 calculated for CigH^ClFNaCbS: 389).
Example 32
In analogy to example 1, on reaction of 5-(2-cWoro-phenyI)-pyridin-2-ylarnine with 3-chloro-4-methoxy-benzenesulfonyl chloride there was obtained: 3-Chloro-N-[5-(2-chloro-phenyl)-pyridin-2-yl]-4-methoxy-benzenesulfonamide as a white solid. ISP mass spectrum, m/e: 409.2 (M+l calculated for CisHuCbNzOjS: 409).
Example 33
In analogy to example 1, on reaction of 5-(2-chloro-phenyl)-pyridin-2-ylamine with 4,5-dichloro-2-fluoro-benzenesulfonyl chloride there was obtained: 4,5-Dichloro-N-[5-(2-chloro-phenyl)-pyridin-2-yl]-2-fluoro-benzenesulfonamide as a white solid. ISP mass spectrum, m/e: 431.2 (M+l calculated for C^HioCUFNaOsS: 431).
Example 34
.n analogy to example 1, on reaction of 5-(2,4-dichloro-phenyl)-pyridin-2-ylamine with 3-•iloro-4-methoxy-benzenesulfonyl chloride there was obtained: 3-Chloro-N-[5-(2,4-lichloro-phenyl)-pyridin-2-yl]-4-methoxy-benzenesulfonamide as an crystalline white olid. ISP mass spectrum, m/e: 443.1(M+1 calculated for QgHisCyS^S: 443).
Example 35
In analogy to example 1, on reaction of 5-(2,4-dichloro-phenyl)-pyridin-2-ylamine with 3-cUoro-4-methyl-benzenesulfonyl chloride there was obtained: 3-Chloro-N-[5-(2,4-dichloro-phenyl)-pyridin-2-yl]-4-methyl-benzenesuuconamide as an crystalline white solid. ISP mass spectrum, m/e: 427.2 (M+l calculated for QgHuCy^C^S: 427).
Example 36
A solution of 0.23 g (1 mmol) of 5-(2,4-dichloro-phenyl)-pyridin-2-ylamine and 0.2 g (1.1 mmol) of piperidine-1-sulfonyl chloride (preparation: Bull.Soc.Chim.Fr.; 1936, p2143) in pyridine (10 ml) was heated to reflux until completion of reaction according to HPLC analysis (20 h). After concentration in vacuo the residue was taken up in EtOAc, which was then washed with IN aqueous HQ, saturated brine, dried over sodium sulphate and concentrated in vacuo. The residue was applied to a silica gel column with EtOAc/toluene (9/1 to 1/1) as duent Combination of the purified fractions and concentration in vacuo gave 0.26 g (67%) of the desired piperidine-1-sulfonic acid [5-(2,4-dichloro-phenyl)-pyridin-2-yl] -amide as a brown crystalline solid. ISN mass spectrum, m/e: 384 (M-l calculated for QeHnCUNAS: 384).
Example 37
'.n analogy to example 1, on reaction of 5-(2,3-dichloro-phenyl)-pyridin-2-ylamine with 2-rifluoromethyl-benzenesulfonyl chloride there was obtained: N-[5-(2,3-Dichloro-)henyl)-pyridin-2-yl]-2-trifluoromethyl-benzenesulfonamide as a light-red solid. ISN nass spectrum, m/e: 445 (M-l calculated for C18HiiCl?F3N2O2S: 445).
Example 38
i analogy to example 1, on reaction of 5-(2^-dichloro-phenyl)-pyridin-2-ylamine with 4-uoro-benzenesulfonyl chloride there was obtained: N-[5-(2,3-Dichloro-phenyl)-pyridin--yl]-4-fluoro-benzenesulfonamide as a white solid. ISN mass spectrum, m/e: 395 (M-l dculated for Ci7HijCl2FN2O2S: 395).
Example 39
a) In analogy to example 1, on reaction of 5-(2,5-dichloro-phenyl)-pyridin-2-ylamine with
2,5-difluoro-benzenesulfonyl chloride there was obtained: N-[5-(2,5-Dichloro-phenyl)-
pyridin-2-yl] -2,5-difluoro-benzenesulfonamide as a light yellow amorphous solid. ISN
mass spectrum, m/e: 413 (M-l calculated for CnHioC^NaChS: 413).
Preparation of the starting material:
b) In analogy to example Ib), on reaction of 5-bromo -pyridin-2-ylamine with 2,3-
dichloro-phenylboronic acid there was obtained: 5-(2,5-dichloro-phenyl)-pyridiu-2-
ylamine as an of-white crystalline solid. El mass spectrum, m/e: 239.1 (M calculated for
CUH8CL2N2: 239).
Example 40
In analogy to example 1, on reaction of 5-(2,5-dichloro-phenyl)-pyridin-2-ylamine with 5-fluoro-2-methyl-benzenesulfonyl chloride there was obtained: N-[5-(2,5-Dichloro-phenyl)-pyridin-2-yl]-5-fluoro-2-methyl-benzenesulfonamide as an off-white solid. ISN mass spectrum, m/e: 409 (M-1 calculated for QgHuClzFNzCbS: 409).
Example 41
In analogy to example 1, on reaction of 5-(2,5-dichloro-phenyl)-pyridin-2-ylainine with 3-chloro-2-methyl-benzenesulfonyl chloride there was obtained: 3-Chloro-N-[5-(2,5-dichloro-phenyl)-pyridin-2-yl]-2-methyl-benzenesulfonamide as a white solid. ISN mass spectrum, m/e: 427.1 (M-l calculated for CigH^CljNaOaS: 427).
Example 42
a) In analogy to example 1, on reaction of 5-(2-fluoro-5-trifluoromethyl -phenyl)-pyridin-2-ylamine with 5-fluoro-2-methyl-benzenesulfbnyl chloride there was obtained: 5-Fluoro-N-[5-(2-fluoro-5-trifluoromethyl-phenyl)-pyridin-2-yl]-2-methyl-benzenesulfonamideas a white solid solid. ISN mass spectrum, m/e:427.2 (M-l calculated for 427).
Preparation of the starting material:
b) In analogy to example Ib), on reaction of 5-bromo -pyridin-2-ylamine with 2-fluoro-5-trifluoromethyl-phenylboronic acid there was obtained: 5-(2-fluoro-5-trifluoromethyl -phenyl)-pyridin-2-ylamine as a white solid. ISP mass spectrum, m/e: 257 (M+H calculated for C12HgF4N2:257).
Example 43
In analog}' to example 1, on reaction of 5-(2-fluoro-5-trifluoromethyl -phenyl)-pyridu>2-ylamine with 3-chloro-2-methyl-benzenesulfonyl chloride there was obtained: 3-Chloro-N-[5-(2-fluoro-5-trifluoromethyl-phenyl)-pyridin-2-yl]-2-methyl-benzenesulfonamideas a white solid ISN mass spectrum, m/e: 442.9 (M-l calculated for Ci9Hi3ClF4N2O2S: 443).
Example 44
a) In analogy to example 1, on reaction of 5-(2-trifluoromethyl -phenyl)-pyridin-2-ylamine with 3-chloro-2-methyl-benzenesulfonyl chloride there was obtained: 3-Chloro-2-methyl-N-[5-(2-trifluoromethyl-phenyl)-pyridin-2-yl]-benzenesulfonamide as an orange solid. ISN mass spectrum, m/K 425 (M-l calculated for C^HuOFsNzOzS: 425).
Preparation of the starting material:
3) In analogy to example Ib), on reaction of 5-bromo -pyridin-2-ylamine with 2-lifluoromethyl-phenylboronic acid there was obtained: 5-(2-trifiuoromethyl-phenyl)-pyridin-2-ylamine as a white solid. ISP mass spectrum, m/e: 239.2 (M+H calculated for :12H9F3N2:239).
Example 45
n analogy to example 1, on reaction of 5-(2-trifluoromethyl -phenyl)-pyridin-2-ylamine vith 3-chloro-4-methyl-benzenesulfonyl chloride there was obtained: 3-Chloro-4-methyl-'J-[5-(2-trifluoromethyl-phenyl)-pyridin-2-yl]-benzenesulfonamide as a light-grey solid olid. ISP mass spectrum, m/e: 425 (M-l calculated for Ci9HHClF3N2O2S: 425).
Example 46
In analogy to example 1, on reaction of 5-(2,4-dicUoro-phenyl)-pyridin-2-ylamine with 5-chloro-2-methoxy-benzenesulfonyl chloride there was obtained: 5-chloro-N-[5-(2,4-dichloro-phenyl)-pyridin-2-yl]-2-methoxy-benzenesulfonainide as a crystalline white solid. ISP mass spectrum, m/e: 443.1 (M+l calculated for Ci8Hi3Cl3N2O3S: 443).
Example 47
lii analogy to example 1, on reaction of 5-(2,4-dichloro-phenyl)-pyridin-2-ylainine with 4-acetylamino-3-chloro-benzenesulfonyl chloride there was obtained: N-{2-Chloro-4-[5-(2,4-dichloro-phenyl)-pyridin-2-ylsulfamoyl]-phenyI}-acetamide as a crystalline brown solid. ISN mass spectrum, m/e: 468 (M-l calculated for C^HuCUNsC^S: 468).
Example 48
In analogy to example 1, on reaction of 5-(2,4-dichloro-phenyl)-pyridin-2-ylamine with 4-trifluoromethyl-benzenesulfonyl chloride there was obtained: N-[5-(2,4-Dichloro-phenyl)-pyridin-2-yl]-4-trifluoromethyl-benzenesulfonamide as a crystalline white solid. ISN mass spectrum, m/e: 445 (M-l calculated for QgHijCUFs^C^S: 445)
Example 49
In analogy to example 1, on reaction of 5-(2,4-dichloro-phenyl)-pyridin-2-ylamine with 4-methylsulfonyl-benzenesulfonyl chloride there was obtained: N-[5-(2,4-Dichloro-phenyl)-pyridin-2-yl]-4-methysulfonyl-benzenesulfonamide as a crystalline light-brown solid. ISN mass spectrum, m/e: 455.1 (M-l calculated for QgHuC^^QiSa: 455).
Example 50
a) In analogy to example 1, on reaction of 5-(2,3-difluoro-phenyl)-pyridin-2-ylamine with 3-chloro-4-methyl-benzenesulfonyl chloride there was obtained: 3-Chloro-N-[5-(2,3-
difiuoro-phenyl)-pyridin-2-yl]-4-methyl-benzenesulfonamide as a white solid. ISN mass spectrum, m/e: 392.9 (M-l calculated for CigHiaClF^C^S: 393).
Preparation of the starting material:
b) In analogy to example Ib), on reaction of 5-bromo -pyridin-2-ylamine with 2,3-difluoro-phenylboronic acid there was obtained: 5-(2,3-difluoromethyl-phenyl)-pyridin-2-ylamine as a white solid. ISP mass spectrum, m/e: 207.2 (M+H calculated for CnHgF^Sb 207).
Example 51
In analogy to example 1, on reaction of 5-(2,3-difluoro-phenyl)-pyridin-2-ylaminewith 3-fluoro-2-methyl-benzenesulfonyl chloride there was obtained: N-[5-(2,3-Difluoro-phenyl)-pyridin-2-yl]-5-fluoro-2-methyl-benzenesuLfonamide as a white solid. ISN mass spectrum, m/e: X377.2 (M-l calculated for QsHisFsNzC^S: 377).
Example 52
a) In analogy to example 1, on reaction of 5-(2,4-bis-trifluoromethyl-phenyi)-pyridin-2-
ylamine with 3-chloro-2-methyl-benzenesulfonyl chloride there was obtained: N-[5-(2,4-
Bis-trifluoromethyl-phenyl)-pyridin-2-yl] -3-chloro-2-methyl-benzenesulfonamide as a
white solid. ISN mass spectrum, m/e: 493 (M-l calculated for CzoHiuClFeNzChS: 493).
Preparation of the starting material:
b) In analogy to example Ib), on reaction of 5-bromo -pyridin-2-ylamine with 2,4-bis-
trifluoromethyl-phenylboronic acid there was obtained: 5-(2,4-bis-trifluoromethyl-
phenyl)-pyridin-2-ylamine as a white solid. ISP mass spectrum, m/e: 307.2 (M+l
calculated for Ci3H8F6N2:307).
Example 53
a) In analogy to example 1, on reaction of 5-(2,4-bis-trifluoromethyl-phenyl)-pyridin-2-ylamine with 3-chloro-4-methyl-benzenesulfonyl chloride there was obtained: N-[5-(2,4-Bis-trifluoromethyl-phenyl)-pyridin-2-yl] -3-cUoro-4-melLyl-benzenesulfonamide as a white solid. ISN mass spectrum, m/e: 493 (M-l calculated for C2oHi3ClF6N2O2S: 493).
Example 54
In analogy to example 1, on reaction of 5-(2,3-difluoro-phenyl)-pyridin-2-ylamine with 3-chloro-2-methyl-benzenesulfonyl chloride there was obtained: 3-Chloro-N-[5-(2,3-difluoro-phenyl)-pyridin-2-yl]-2-methyl-benzenesulfonamide as a white solid. ISN mass spectrum, m/e: 392 (M-l calculated for CisHnClFzNzOjS: 392).
Example 55
In analogy to example XX, on reaction of 5-(2,3-dichloro-phenyl)- pyridkt-2-yiamine with piperidine-1-sulfonyl chloride there was obtained: Piperidine-1-sulfonic acid [5-(2,3-dichloro-phenyl)-pyridin-2-yl]-amide as an off-white solid. ISN mass spectrum, m/e: 384(M-1 calculated for QeHnClzNaCbS: 384).
Example 56
In analogy to example 1, on reaction of 5-(4-fluoro-phenyl)-6-methyl-pyridin-2-ykmine with 5-chloro-2-methoxy-benzenesulfonyl chloride there was obtained: 5-Chloro-N-[5-(4-fluoro-phenyl)-6-methyl-pyridin-2-yl]-2-methoxy-benzenesulfonamide as a crytalline white solid. ISN mass spectrum, m/e: 405.2 (M-l calculated for Ci9Hi6ClFN2O3S: 405).
Example 57
In analogy to example 1, on reaction of 5-(4-fluoro-phenyl)-6-methyl-pyridin-2-ylamine with 4-acetylamino3-chloro-benzenesulfonyl chloride there was obtained: N-{2-Chloro-4-[5-(4-fluoro-phenyl)-6-methyl-pyridin-2-ylsulfamoyl]-phenyl}-acetamide as a light-brown solid. ISN mass spectrum, m/e: 432.2 (M-l calculated for C2oHi7ClFN3O3S: 432).
Example 58
In analogy to example 1, on reaction of 5-(4-fluoro-phenyl)-6-methyl-pyridin-2-ylamine with 4-trifluonnethyl-benzenesulfonyl chloride there was obtained: N-[5-(4-Fluoro-phenyl)-6-methyl-pyridin-2-yi]-4-trifluoromethyl-benzenesulfonamide as a brown foam. ISN mass spectrum, m/e: 409 (M-l calculated for Ci9Hi4F4N2O2S: 409).
Example 59
In analogy to example 1, on reaction of 5-(4-fluoro-phenyl)-6-methyl-pyridih-2-ylamine with 4-methanesulfonyl-benzenesulfonyi chloride there was obtained: N-[5-(4-Fluoro-phenyl)-6-methyl-pyridin-2-yl]-4-methanesulfonyl-benzenesulfonamide as a brown viscous oil. ISN mass spectrum, m/e: 419 (M-l calculated for QgH^FNaC^S^419).
Example 60
In analogy to example 1, on reaction of 5-(2)3-dichloro-phenyl)-pyridin-2-ylamine with (4-chlorosulfonyl-phenoxy)-acetic acid methyl ester there was obtained: {4-[5-(2,3-dichloro-phenyl)-pyridin-2-ylsulfamoyl]-phenoxy}-acetic acid methyl ester as a white solid. ISN mass spectrum, m/e: 465 (M-l calculated for QoHieCbN^sS: 465).
Example 61
In analogy to example 1, on reaction of 5-(4-fluoro-phenyl)-6-methyl-pyridin-2-ylamine with 4-trifluoromethoxy-benzenesulfonyl chloride there was obtained: N-[5-(4-FJuorophenyl)-6-memyl-pyridin-2-yl]-4-trifluoromethoxy-benzejiesulfonarnide as a light-brown foam. ISP mass spectrum, m/e: 427.3 (M+l calculated for C^H^N^S: 427).
Example 62
In analogy to example 1, on reaction of 5-(4-fluoro-phenyl)-6-methyl-pyridin-2-ylamine with 3-chloro-4-methoxy-benzenesulfonyl chloride there was obtained: 3-Chloro-N-[5-(4-fluoro-phenyl)-6-methyl-pyridin-2-yl]-4-methoxy-benzenesulfonamide as a light-brown foam. ISN mass spectrum, m/e: 405.1 (M-l calculated for Ci9Hi6ClFN2O3S: 405).
Example 63
In analogy to example 1, on reaction of 5-(4-fluoro-phenyl)-6-methyl-pyridin-2-ylamine with 4-chloro-2,5-dimethyl-benzenesulfonyl chloride there was obtained: 4-Chloro-N-[5-(4-fluoro-phenyl)-6-methyl-pyridin-2-yl]-2,5-dimethyl-benzenesulfonamide as a light-brownfoam. ISN mass spectrum, m/e: 403.1 (M-1 calculated for CzoHisClFNzC^S: 403).
Example 64
A solution of 120 mg (2.6 mmol) of 4-[5-(2,3-Dichloro-phenyl)-pyridin-2-ylsuhtamoyl]-phenoxyj-acetic add methyl ester, product of example 60, in THF/EtOH (each 5 ml) was treated with 57 mg (5.1 mmol) of CaCl2, cooled to 0° C and then 39 mg (1 mmol) of sodium borohydride were added portionwise. The mixture was stirred for 12 h at RT, poured into ice/water acidified with 3 M HCl to pH 1 and extracted with AcOEL.The layers were separated, the organic layer dried over sodium sulphate and concentrated in vacuo. The residue was applied to a silica gel column with EtOAc/heptan (1/1) then CHjCla/MeOH (95/5) as eluent. Combination of the purified fractions and concentration in vacuo gave 0.1 g (93%) of the desired N-[5-(2,3-Dichloro-phenyl)-pyridin-2-yl]-4-(2-hydroxy-ethoxy)-benzenesulfonamide as white foam. ISN mass spectrum, m/e: 437.2 (M-1 calculated for QsHisClzN^S: 437).
Example 65
In analogy to example 1, on reaction of 5-(2-chloro-phenyl)-6-methyl-pyridin-2-ylamine with 4-fluoro-benzenesulfonyl chloride there was obtained: N-[5-(2-Chloro-phenyl)-6-methyl-pyridin-2-yl]-4-fluoro-benzenesulfonamide as a white foam. ISN mass spectrum, m/e: 375.2 (M-1 calculated for Ci8Hi4ClFN2O2S: 375).
Example 66
In analogy to example 1, on reaction of 5-(2-chloro-phenyl)-6-methyl-pyridin-2-ylamine with 3-chloro-4-methyl-benzenesulfonyl chloride there was obtained: 3-Chloro-N-[5-(2-
chloro-phenyl)-6-methyl-pyridin-2-yl]-4-methyl-benzenesulfonainide as a white foam. ISN mass spectrum, m/e: 405.2 (M-l calculated for CisHtfCfeNzOaS: 405).
Example 67
In analogy to example 1, on reaction of 5-(2-chloro-phenyl)-6-methyl-pyridin-2-ylamine with 4-chloro-benzenesulfonyl chloride there was obtained: 4-Chloro-N-[5-(2-chloro-phenyl)-6-methyl-pyridin-2-yl]-benzenesuh Examle 68
In analogy to example 1, on reaction of 5-(2-chloro-phenyl)-6-methyl-pyridin-2-ylamine with 4,6-dichloro-2-methyl-benzenesulfonyl chloride there was obtained: 2,4-Dichloro-N-[5-(2-chloro-phenyl)-6-methyl-pyridin-2-yl]-6-methyl-benzenesulfonamide as a white foam. ISN mass spectrum, m/e: 439 (M-l calculated for C^HjsCySkOaS: 439).
Example 69
In analogy to example 36, on reaction of 5-(2-chloro-phenyl)-6-methyl-pyridin-2-ylamine with 4 piperidine-1-sulfonyl chloride there was obtained: Piperidine-1-sulfonic acid [5-(2-chloro-phenyl)-6-methyl-pyridin-2-yl]-amide as a white foam. ISN mass spectrum, m/e: 364 (M-l calculated for Ci7H2oClN3O2S: 364).
Example 70
In analogy to example 1, on reaction of 5-(2,4-dichloro-phenyl)-pyridin-2-ylamine with 4-fluoro-benzenesulfonyl chloride there was obtained: N-[5-(2,4-Dichloro-phenyl)-pyridin-2-yl]-4-fluoro-benzenesulfonamide as a crystalline white solid. ISN mass spectrum, m/e: 394.9 (M-l calculated for CnHnCUFNzC^S: 395).
Example 71
In analogy to example 1, on reaction of 5-(2,4-dichloro-phenyl)-pyndin-2-ylamine wiui 4-chloro-2,5-dimethyl-benzenesulfonyl chloride there was obtained: 4-Chloro-N-[5-(2,4-dichloro-phenyl)-pyridin-2-yl]-2,5-dimethyl-benzenesulfonamide as an amorphous white solid. ISN mass spectrum, m/e: 439 (M-l calculated for Ci9Hi5Cl3N2O2S: 439).
Example 72
In analogy to example 1, on reaction of 5-(2,4-dichloro-phenyl)-pyridin-2-ylamine with 2,4-difluoro-benzenesuifonyl chloride there was obtained: N-[5-(2,4-dichloro-phenyl)-pyrioUn-2-yl]-2,4-difluoro-benzenesulfonarnide as a crystalline white solid. ISN mass spectrum, m/e: 413.1 (M-l calculated for CnHioClaFa^C^S: 413).
Example 73
In analogy to example 1, on reaction of 5-(2,4-dichloro-phenyl)-pyridin-2-ylamine with 2,4-dichloro-5-methyl-benzenesulfonyl chloride there was obtained: 2,4-Dichloro-N-[5-(2,4-dichloro-phenyl)-pyridin-2-yl]-5-methyl-benzenesulfonamide as a amorphous white solid. ISN mass spectrum, m/e: 459 (M-l calculated for QgHnCL^NjOzS: 459).
Example 74
In analogy to example 1, on reaction of 5-(2,3-dichloro-phenyl)-pyridin-2-ylamine with 3-trifluoromethyl-benzenesulfonyl chloride there was obtained: N-[5-(2,3-Dichloro-phenyl)-pyridin-2-yl]-3-trifluoromethyl-benzenesulfonamide as an off-white solid. ISN mass spectrum, m/e: 445 (M-l calculated for QsHnCyFaNaOaS: 445).
Example 75
a) In analogy to example 1, on reaction of 5-(4-nuoro-2-methyl-phenyl)-6-methyl-pyridin-2-ylamine with 4-fluoro-benzenesulfonyl chloride there was obtained: 4-Fluoro-N-[5-(4-fluoro-2-methyl-phenyl)-6-methyl-pyridin-2-yl]-benzenesulfonamide as a white foam. ISN mass spectrum, m/e: 373.1 (M-l calculated for C^Hi^NiC^S: 373).
Preparation of the starting material:
b) In analogy to example Ib), on reaction of 5-bromo -6-methyl-pyridin-2-ylamine with 4-fluoro-2-methyl-phenylboronic acid there was obtained: 5-(4-Fluoro-2-methyl-phenyl)-6-methyl-pyridin-2-ylamine as a yellow solidwhich was used directly in the next reaction step.
Example 76
In analogy to example 1, on reaction of 5-(4-fluoro-2-methyl-phenyl)-6-methyl-pyridin-2-ylarmne with 3-chloro-2-methyl-benzenesulfonyl chloride there was obtained: 3-Chloro-N-[5-(4-fluoro-2-methyl-phenyl)-6-memyl-pyri6Un-2-yl]-2-rnethyl-benzenesulfonamide as a white foam. ISN mass spectrum, m/e: 403.2 (M-l 403).
Example 77
In analogy to example 1, on reaction of 5-(4-nuoro-2-methyl-phenyl)-6-methyl-pyridin-2-ylamine with 5-fiuoro-2-methyl-benzenesulfonyl chloride there was obtained: 5-Fluoro-N-[5-(4-fluoro-2-methyl-phenyl)-6-memyl-pyridin-2-yl]-2-methyl-benzenesulfonamide as awhite solid. ISN mass spectrum, m/e: 387.1 (M-l calculated for C^^^OzS: 387).
Example 78
In analogy to example 1, on reaction of 5-(2,3-dichloro-phenyl)-pyridin-2-ylamine with 3-chloro-4-methyl-benzenesulfonyl chloride there was obtained: 3-Chloro-N-[5-(2,3-dichloro-phenyl)-pyridin-2-yl]-4-methyl-benzenesulfonamide as awhite solid. ISN mass spectrum, m/e: 425 (M-l calculated for QgHisCySIaChS: 425).
Example 79
In analogy to example 1, on reaction of 5-(2,3-dichloro-phenyl)-pyridin-2-yiamine with 4-trifluoromethyl-benzenesulfonyl chloride there was obtained: N-[5-(2,3-Dichloro-phenyl)-pyridin-2-yl]-4-trifluoromethyl-benzenesulfonamide as a white solid. ISN mass spectrum, m/e: 444.9 (M-l calculated for QgHnCkFs^OaS: 445).
Example 80
a) In analogy to example 1, on reaction of 5-(4-fluoro-2-methyl-phenyl)-pyridin-2-ylamine with 3-chloro-4-methyl-benzenesulfonyl chloride there was obtained: 3-Chloro-N-[5-(4-fluoro-2-methyl-phenyl)-pyridin-2-yl]-4-methyl-benzenesulfonamide as a white solid. ISN mass spectrum, m/e: 389 (M-l calculated for CigHisClF^C^S: 389).
Example 81
a) In analogy to example 1, on reaction of 5-(4-fluoro-2-methyl-phenyl)-pyridin-2-ylaminewith 3-trifl.uoromethyl-benzenesulfonyl chloride there was obtained: N-[5-(4-Fluoro-2-methyl-phenyl)-pyridin-2-yl]-3-trifluoromethyl-benzenesulfonamide as a white solid. ISN mass spectrum, m/e: 409 (M-l calculated for Ci9Hi4F4N2O2S: 409).
gxample 82
a) In analogy to example 1, on reaction of 5-(4-fluoro-2-methyl-phenyl)-pyridin-2-ylamine with 4"trifluoromethyl-benzenesulfonyl chloride there was obtained: N-[5-(4-Fluoro-2-methyl-phenyl)-pyridin-2-yl]-4-trifluoromethyl-benzenesulfonamide as a white solid. ISN mass spectrum, m/e: 409 (M-l calculated for QgHiANaC^S: 409).
Example 83
In analogy to example 1, on reaction of 5-(2-chloro-phenyl)-pyridin-2-ylamine with 3-trifluromethyl-benzenesulfonyl chloride there was obtained: N-[5-(2-Chloro-phenyl)-pyridin-2-yl]-3-trifluoromethyl-benzenesulfonamide as a white solid. ISN mass spectrum, m/e: 411 (M-l calculated for CigHnClFa^OBS: 411).
Example 84
In analogy to example 1, on reaction of 5-(2-chloro-phenyl)-pyridin-2-ylamine with 4-ethyl-benzenesulfonyl chloride there was obtained: N-[5-(2-Chloro-phenyl)-pyridin-2-yl]-4-ethyl-benzenesulfonamide as a white solid. ISN mass spectrum, m/e: 371.1 (M-l calculated for C^
Example 85
In analogy to example 1, on reaction of 5-(2-chloro-phenyl)-pyridin-2-ylamine with 3-chloro-benzenesulfonyl chloride there was obtained: 3-Chloro-N-[5-(2-chloro-phenyl)-pyridin-2-yl]-benzenesulfonamide as white crystals. ISN mass spectrum, m/e: 377.1 (M-l calculated for CnHuQiNjOsS: 377).
Example 86
In analogy to example 1, on reaction of 5-(2,4-dichloro-phenyl)-pyridin-2-ylamine with 3-chloro-4-fluoro-benzenesulfonyl chloride there was obtained: 3-Chloro-N-[5-(2,4-dichloro-phenyl)-pyridin-2-yl]-4-fluoro-benzenesulfonamide as a crystalline white solid. ISN mass spectrum, m/e: 429.1 (M-l calculated for CnHioCljF^OaS: 429).
Example 87
In analogy to example 1, on reaction of 5-(2,4-dichl6ro-phenyl)-pyridin-2-ylamine with 4-ethyl-benzenesulfonyl chloride there was obtained: N-[5-(2,4-Dichloro-phenyl)-pyridin-2-yl]-4-ethyl-benzenesulfonamide as a crystalline white solid, ISN mass spectrum, m/e: 405.1 (M-l calculated for CuHigCkNzOzS: 405).
Example 88
a) In analogy to example 1, on reaction of 5-(2,4-dichloro-phenyl)-pyridin-2-ylamine with 3-trifluoromethyl-benzenesulfonyl chloride there was obtained: N-[5-(2,4-Dichloro-
phenyl)-pyridin-2-yl]-3-trifluoromethyl-benzenesulfonamide as an white foam. ISP mass spectrum, m/e: 444.9 (M-1 calculated for d8 HuCfcFstyC^ S: 445).
Example 89
In analogy to example 1, on reaction of 5-(2-chloro-phenyl)-6-methyl-pyridin-2-yianiine with 3-trifluoromethyl-benzenesulfonyl chloride there was obtained: N-[5-(2-Chloro-phenyl)-6-methyl-pyridin-2-yl]-3-trifluoromethyl-benzenesulfonamide as a white foam. ISN mass spectrum, m/e: 425 (M-1 calculated for C]9 Hi4ClF3N2O2S: 425).
Example 90
In analogy to example 1, on reaction of 5-(2-chloro-phenyi)-6-methyl-pyridin-2-ylamine with 4-trifluoromethoxy-benzenesulfonyl chloride there was obtained: N- [5-(2-Chloro-phenyl)-6-methyl-pyridin-2-yl]-4-trifluoromethoxy-benzenesulfonamide as a white foam. ISN mass spectrum, m/e: 441.1 (M-1 calculated for Q9 HuClFs^OsS: 441).
Example 91
In analogy to example 1, on reaction of 5-(2-chloro-phenyl)-pyridin-2-ylamine with 4-fluoro-benzenesulfonyl chloride there was obtained: N-[5-(2-Chloro-phenyl)-pyridin-2-yl]-4-fluoro-benzenesulfonamide as a white solid. ISN mass spectrum, m/e: 361 (M-1 calculated for Ci7Hi2ClFN2O2S: 361).
Example 92
In analogy to example 1, on reaction of 5-(2-chloro-phenyI)-pyridin-2-ylamine with 2,4-difluoro-benzenesulfonyl chloride there was obtained: N-[5-(2-Chloro-phenyl)-pyridin-2-yl]-2,4-difluoro-benzenesulfonamide as a white solid. ISN mass spectrum, m/e: 379 (M-1 calculated for Ci7HiiClF2N2O2S: 379).
Example 93
In analogy to example 1, on reaction of 5-(2-chloro-phenyl)-pyridin-2-ylamine with 4-chloro-2,5-dimethyl-benzenesulfonyl chloride there was obtained: 4-Chloro-N-[5-(2-chloro-phenyl)-pyridin-2-yl]-2,5-dimethyl-benzenesuhconamide as a white solid. ISN mass spectrum, m/e: 405.1 (M-l calculated for CigHisClztyC^S: 405).
Example 94
In analogy to example 1, on reaction of 5-(2-chloro-phenyl)-6-methyl-pyridin-2-ylamine with 4-chloro-2,5-dimethyl-benzenesulfonyl chloride there was obtained: 4-Chloro-N-[5-(2-chloro-phenyl)-6-methyl-pyridin-2-yl]-2>5-dimethyl- benzenesulfonamide as an off-white solid, ISN mass spectrum, m/e: 419 (M-l calculated for CM HigCWSTzC^S: 419).
Example 95
In analogy to example 1, on reaction of 5-(2-chloro-phenyl)-6-methyl-pyridin-2-ylaniine with 2,4-difluoro-benzenesulfonyl chloride there was obtained: N-[5-(2-Chloro-phenyl)-6-methyl-pyridm-2-yl]-2,4-difluoro-benzenesulfonamide as an off-white solid. ISN mass spectrum, m/e: 392.9 (M-f 1 calculated for Q8 HnClFa^OaS: 393).
Example 96
In analogy to example 1, on reaction of 5-(2-chloro-phenyl)-6-methyl-pyridin-2-ylamine with 3,5-dichloro-benzenesulfonyl chloride there was obtained: 3,5-Dichloro-N-[5-(2-chloro-phenyl)-6-methyl-pyridin-2-yl]-benzenesulfonamide as an off-white solid. ISN mass spectrum, m/e: 425 (M-l calculated for C18 HisCUN^S: 425).
Example 97
a) In analogy to example 1, on reaction of 5-(2,4-chloro-phenyl)-6-methyl-pyridin-2-ylamine with 3-trifluoromethyl-benzenesulfonyl chloride there was obtained: N-[5-(2,4-Dichloro-phenyl) -6-methyl-pyridin-2-yl] -3-trinuoromethyl-benzenesulfonamide as an colourless waxy solid. ISN mass spectrum, m/e: 459 (M-l calculated for Qg H13C12F3N202S: 459).
Preparation of the starting material:
b) In analogy to example Ib), on reaction of 5-bromo -6-methyl-pyridin-2-ylamine with 2,4-dichloro-phenylboronic acid there was obtained: of 5-(2,4-chloro-phenyl)-6-methyl-pyridin-2-ylamine as a brown crystalline solid. ISP mass spectrum, m/e: 253 (M+l calculated for C12Hi0C12N2: 253).
Example 98
In analogy to example 1, on reaction of 5-(2,4-chloro-phenyl)-6-methyi-pyridin-2-ylamine with 4-fluoro-benzenesulfonyl chloride there was obtained: N-[5-(2,4-Dichloro-phenyl)-6-methyl-pyridin-2-yl]-4-fluoro-benzenesulfonamide as an colorless waxy solid. ISn mass spectrum, m/e: 409 (M-l calculated for Ci8 Hi3Cl2FN2O2S: 409).
Example 99
In analogy to example 1, on reaction of 5-(2,4-chloro-phenyl)-6-methyl-pyridin-2-ylamine with 2,4-difluoro-benzenesulfonyl chloride there was obtained: N-[5-(2,4-Dichloro-phenyl)-6-methyl-pyridin-2-yl]-2,4-difluoro-benzenesulfonamide as a colorless foam. ISN mass spectrum, m/e: 427.1 (M-l calculated for Ci8Hi2CI2F2N2O2S: 427).
Example 100
In analogy to example 1, on reaction of 5-(2,4-cWoro-phenyl)-6-methyl-pyridin-2-ylamine with 4-chloro-2>5-dimethyl-benzenesulfonyl chloride there was obtained: 4-Chloro-N-[5-(2,4-dichloro-phenyl)-6-methyl-pyridin-2-yl]-2,5-dimethyl-benzenesulfonamide as a white powder. ISN mass spectrum, m/e: 453.1 (M-l calculated for C2oHi7Cl3N2O2S: 453).
Example 101
a) In analogy to example 1, on reaction of 5-(2>4-dichloro-phenyl)-pyridin-2-ylamine with 2)4-dichloro-6-methyl-benzenesulfonyl chloride there was obtained: 2,4-Dichloro-N-[5-(2>4-dichloro-phenyl)-pyridin-2-yl]-6-methyl-benzenesulfonamide as a white foam. ISN mass spectrum, m/e: 458.9 (M-l calculated for Ci8H12CUN2O2S: 458).
Example 102
a) In analogy to example 1, on reaction of 5-(2,4-dichloro-phenyl)-pyridin-2-ylamine with 3-chloro-benzenesulfonyl chloride there was obtained: 3-Chloro-N-[5-(2,4-dicbloro-phenyl)-pyridin-2-yl]-benzenesulfonamide as an off-white foam. ISN mass spectrum, m/e: 411 (M-l calculated for CnHiiCls^ChS: 411).
Example 103
a) In analogy to example 1, on reaction of 5-(2,4-dichloro-phenyl)-pyridin-2-ylamine with 4-chloro-benzenesulfonyl chloride there was obtained: 4-Chloro-N-[5-(2,4-dichloro-phenyl)-pyridin-2-yl]-benzenesulfonamide as an off-white foam. ISP mass spectrum, m/e: 411 (M-l calculated for Ci7HuCl3N2O2S: 411).
Example 104
In analogy to example 1, on reaction of 5-(2-chloro-phenyl)-6-methyi-pyridin-2-ylamine with 3-fluoro-benzenesulfonyl chloride there was obtained: N-[5-(2-Chloro-phenyl)-6-methyl-pyridin-2-yl]-3-fluoro-benzenesulfonamide as an light-yellow foam. ISN mass spectrum, m/e: 375.2 (M-l calculated for Ci8 Hi4ClFN2O2S: 375).
Example 105
In analogy to example 1, on reaction of 5-(2-chloro-phenyl)-6-methyi-pyridin-2-ylamine with 3-chloro-benzenesulfonyl chloride there was obtained: 3-Chloro-N-[5-(2-chloro-phenyl)-6-methyl-pyridin-2-yl]-benzenesulfonamide as a light-yellow foam. ISN mass spectrum, m/e: 391 (M-l calculated for Ci8 Hi4Cl2N2O2S: 391).
Example 106
In analogy to example 1, on reaction of 5-(2-chloro-phenyl)-6-methyl-pyridin-2-ylamine with 2,4-dichloro-benzenesulfonyl chloride there was obtained: 2,4-Dichloro-N-[5-(2-
chloro-phenyl)-6-methyl-pyridin-2-yI]-benzenesulfonamide as a light-yellow foam. ISN mass spectrum, m/e: 424.9 (M-l calculated for Q8 HuCljNaOiS: 425).
Example 107
In analogy to example 1, on reaction of 5-(2-chloro-phenyi)-6-methyl-pyridin-2-yiamine with 2,4-dichloro-5-methyl-benzenesulfonyl chloride there was obtained: 2,4-Dichloro-N-[5-(2-chloro-phenyl)-6-methyl-pyridin-2-yl]-5-methyl-benzenesulfonainide as a light-yellow foam. ISN mass spectrum, m/e: 439 (M-l calculated for Qg HisCls^C^S: 439).
Example 108
In analogy to example 1, on reaction of 5-(4-fiuoro-2-methyl-phenyl)-6-methyl-pyridin-2-ylamine with 3-trifluomethyl-benzenesulfonyl chloride there was obtained: N-[5-(4-Fluoro-2-me1iiyl-phenyl)-6-methyl-pyridm-2-yl]-3-trifiuoromethyl-benzenesulfonainide as a light-yellow foam. ISN mass spectrum, m/e: 423 (M-l calculated for C2o 423).
ExamplelQg
In analogy to example 1, on reaction of 5-(4-fluoro-2-methyl-phenyl)-6-methyl-pyridin-2-ylamine with 2J4-dichloro-6-methyl-benzenesulfonyl chloride there was obtained: 2,4-Dichloro-N-[5-(4-fluoro-2-methyl-phenyl)-6-methyl-pyridin-2-yl]-6-methyl-benzenesulfonamide as a light-yellow foam. ISN mass spectrum, m/e: 437.2 (M-l calculated for CaoHnCkFNzOzS: 437).
Example 110
In analogy to example 1, on reaction of 5-(4-fluoro-2-methyl-phenyl)-6-methyl-pyridin-2-ylamine with 3-chloro-benzenesulfbnyl chloride there was obtained: 3-Chloro-N-[5-(4-fluoro-2-methyl-phenyl)-6-methyl-pyridin-2-yl]-benzenesulfonarnide as a light-yellow foam. ISN mass spectrum, m/e: 389 (M-l calculated for Ci9H16aFN2O2S: 389).
Example 111
In analogy to example 1, on reaction of 5-(4-fluoro-2-methyi-phenyl)-6-methyl-pyridin-2-ylamine with 4-chloro-benzenesulfbnyl chloride there was obtained: 4-Chloro-N-[5-(4-fluoro-2-methyl-phenyl)-6-methyl-pyridin-2-yl]-benzenesulfonamide as a light-yellow foam. ISN mass spectrum, m/e: 389.1 (M-l calculated for Ci9Hi6ClFN2O2S: 389).
Example 112
In analogy to example 1, on reaction of 5-(4-fluoro-2-methyi-phenyl)-6-methyl-pyridin-2-ylarnine with 4-trifluoromethoxy-benzenesulfonyl chloride there was obtained: N-[5-(4-Fluoro-2-methyl-phenyl)-6-methyl-pyridin-2-yl]-4-trinuoromethoxy-benzenesulfonamide as a light-brown viscous oil ISN mass spectrum, m/e: 439.1 (M-l calculated for C2oHi6F4N2O3S: 439).
Example 113
In analogy to example 1, on reaction of 5-(4-fluoro-2-methyl-phenyl)-6-methyl-pyridin-2-ylamine with 3-methyl-benzenesulfonyl chloride there was obtained: N-[5-(4-Fluoro-2-methyl-phenyl)-6-methyl-pyridin-2-yl]-3-methyl-benzenesulfonamide as a light-yellow viscous oil. ISN mass spectrum, m/e: 369 (M-l calculated for C2oHi9FN2O2S: 369).
Example 114
In analogy to example 1, on reaction of 5-(4-fluoro-2-methyl-phenyl)-6-methyl-pyridin-2-ylamine with 2-chloro-5-trifluoromethyl-benzenesulfonyi chloride there was obtained: 2-Chloro-N-[5-(4-fluoro-2-methyl-phenyl)-6-methyl-pyridin-2-yl]-5-trifluoromethyl-benzenesulfonamide as a light-yellow viscous oil. ISN mass spectrum, m/e: 457.1 (M-l calculated for CMHisC^NaOjS: 457).
Example 115
In analogy to example 1, on reaction of 5-(4-fluoro-2-methyl-phenyl)-6-methyl-pyridin-2-ylamine with 4-fluoro-3-trifluoromethyl-benzenesulfonyl chloride there was obtained:
2-Chloro-N-[5-(4-fluoro-2-methyl-phenyl)-6-methyl-pvridin-2-yl)-5-trifluorometliyl-benzenesulfonamide as a light-brown viscous oil. ISN mass spectrum, m/e: 441.1 (M-l calculated for C^^N^S: 441).
Example 116
In analogy to example 1, on reaction of 5-(2-chloro-phenyl)-6-methyl-pyridin-2-ylamine with 3-methyl-benzenesulfonyl chloride there was obtained: N-[5-(2-Chloro-phenyl)-6-methyl-pyridin-2-yl]-3-methyl-benzenesulfonamide as a light-yellow viscous oil. ISN mass spectrum, m/e: 371.2 (M-l calculated for Cw Hi7ClN2O2S: 371).
Example 117
In analogy to example 1, on reaction of 5-(2-chloro-phenyl)-6-methyl-pyridin-2-ylamine with 3-chloro-4-fluoro-benzenesulfonyl chloride there was obtained: 3-Chloro-N-(2-chloro-phenyl)-6-methyl-pyridin-2-yl]-4-fluoro-benzenesulfonamide as a light-yellow viscous oil. ISN mass spectrum, m/e: 409.3 (M-l calculated for Qg Hi3Cl2FN2O2S: 409).
Example 118
In analogy to example 1, on reaction of 5-(2-chloro-phenyl)-6-methyl-pyridin-2-ylamine with 3-chloro-5-trifluoromethyl-benzenesulfonyl chloride there was obtained: 2-Chloro-N-[5-(2-chloro-phenyl)-6-methyl-pyridin-2-yl]-5-trifluoromethyl-benzenesulfonamideas a light-yellow viscous oil. ISN mass spectrum, m/e: 459.2 (M-l calculated for Ci9H13Cl2F3N2O2S: 459).
Example 119
In analogy to example 1, on reaction of 5-(2-chloro-phenyl)-6-methyl-pyridin-2-ylamine with 4-fluoro-3-trifluoromethyl-benzenesulfonyl chloride there was obtained: N-[5-(2-Chloro-phenyl)-6-methyl-pyridin-2-yl]-4-fluoro-3-trifluoromethyl-benzenesulfonamide as a light-brown viscous oil. ISN mass spectrum, m/e: 442.9 (M-l calculated for C19Hi3ClF4N2O2S: 443).
Example 120
In analogy to example 1, on reaction of 5-(2,3-dichloro-phenyl)-pyridin-2-ylamiiie with 3-fluoro-4-methyi-benzenesulfonyl chloride there was obtained: N-[5-(2,3-Dichloro-phenyl)-pyridin-2-yl]-3-fluoro-4-methyl-benzenesulfonamide as a colorless solid. ISN mass spectrum, m/e: 409.1 (M-l calculated for QgHuCy^C^S: 409).
Example 121
In analogy to example 1, on reaction of 5-(2>3-dichloro-phenyl)-pyridin-2-ylaminewith 3,5-dimethyl-benzenesulfonyl chloride there was obtained: N-[5-(2,3-Dichloro-phenyl)-pyridin-2-yl]-3>5-dimethyi-benzenesulfonamide as a white solid. ISN mass spectrum, m/e: 405.1 (M-l calculated for dsHieC^CbS: 405).
Example 122
a) In analogy to example 1, on reaction of 5-(5-fluoro-2-methyl-phenyl)-pyridin-2-
ylamine with 3-trifluoromethyl-benzenesulfonyl chloride there was obtained: N-[5-(5-
Fluoro-2-methyl-phenyl)-pyridin-2-yl]-3-trifluoromethyl-benzenesulfonamide as a white
solid. ISN mass spectrum, m/e: 409.1 (M-l calculated for QgHi^NaChS: 409). .
Preparation of the starting material:
b) In analogy to example Ib), on reaction of 5-bromo -pyridin-2-ylamine with 5-fluoro-2-
methyl-phenylboronic acid there was obtained: 5-(5-fluoro-2-methyl-phenyi)-pyridin-2-
ylamine as a light yellow oil. ISP mass spectrum, m/e: 203.1 (M+l calculated for
z: 203).
Example 123
a) In analogy to example 1, on reaction of 5-(5-fluoro-2-methyl-phenyl)-pyridin-2-ylamine with 4-fluoro-benzenesulfonyl chloride there was obtained: 4-Fluoro-N-[5-(5-fluoro-2-methyl-phenyl)-pyridin-2-yl]-benzenesulfonamide as a white solid. ISN mass spectrum, m/e: 359 (M-l calculated for QsHiANaOaS: 359).
Example 124
a) In analogy to example 1, on reaction of 5-(5-fluoro-2-methyl-phenyl)-pyridin-2-ylamine with 3-chloro-2-methyl-benzenesulfonyl chloride there was obtained: 3-Chloro-N-[5-(5-fluoro-2-methyl-phenyl)-pyridin-2-yl3-2-methyl-benzenesulfonamide as a white solid. ISN mass spectrum, m/e: 389.1 (M-l calculated for QgHisClFNaOjS: 389).
Example 125
a) In analogy to example 1, on reaction of 5-(5-chloro-2-methyl-phenyl)-pyridin-2-ylamine with 3-trifluoromethyl-benzenesulfonyl chloride there was obtained: N-[5-(5-Chloro-2-methyl-phenyl)-pyridin-2-yl]-3-trifluoromethyl-benzenesulfonamide as an off-white solid. ISN mass spectrum, m/e: 425.1 (M-l calculated for CigHudF^C^S: 425).
Preparation of the starting material:
b) In analogy to example Ib), on reaction of 5-bromo -pyridin-2-ylamine with 5-chloro-2-methyl-phenylboronic acid there was obtained: 5-(5-chloro-2-methyl-phenyl)-pyridin-2-ylamine as a white solid. El mass spectrum, m/e: 218.1 (M calculated for CnHnCINz: 218).
Example 126
In analogy to example 1, on reaction of 5-(5-chloro-2-methyl-phenyl)-pyridin-2-ylamine with 4-fluoro-benzenesulfonyl chloride there was obtained: N-[5-(5-Chloro-2-methyl-phenyl)-pyridin-2-yl]-4-fluoro-benzenesulfonamide as a light-yellow solid. ISN mass spectrum, m/e: 375.2 (M-l calculated for QsHuClFNaChS: 375).
Example 127
in analogy to example 1, on reaction of 5-(5-chloro-2-methyl-phenyl)-pyridin-2-ylamine vith 3-chloro-2-methyl-benzenesulfonyl chloride there was obtained: 3-Chloro-N-[5-(5-
chloro-2-methyl-phenyl)-pyridin-2-yl]-2-methyl-benzenesulfonamide as a white solid. ISN mass spectrum, m/e: 405.1 (M-l calculated for CigH^ClzNiOzS: 405).
Example 128
a) In analogy to example 1, on reaction of 5-(6-Chloro-2-fluoro-3-methyl-phenyl)-pyridin-2-ylamine with 3-chloro-2-methyl-benzenesulfonyl chloride there was obtained: 3-Chloro-N-[5-(6-chloro-2-fluoro-3-methyl-phenyl)-pyridin-2-yl]-2-methyl-benzenesulfonamide as a white solid. ISn mass spectrum, m/e: 422.9 (M-l calculated for NzOzS: 423).
Preparation of the starting material:
b) In analogy to example Ib), on reaction of 5-bromo -pyridin-2-ylamine with 6-Chloro-2-fluoro-3-methyl-phenylboronic acid there was obtained: 5-(5-chloro-2-methyl-phenyl)-pyridin-2-ylamine as awhite solid. El mass spectrum, m/e: 237.1 (M calculated for Ci2HioClFN2: 237).
Example 129
In analogy to example 1, on reaction of 5-(6-Chloro-2-fluoro-3-methyl-phenyl)-pyridin-2-ylamine with 3-trifluoromethyl-benzenesulfonyl chloride there was obtained: N-[5-(6-Chloro-2-fluoro-3-methyl-phenyl)-pyridhi-2-yl]-3-trifluoromethyl-benzenesulfonamide as a light-yellow solid. ISN mass spectrum, m/e: 443.2 (M-l calculated for Ci9H13ClF4N202S: 443).
Example 130
In analogy to example 1, on reaction of 5-(6-Chloro-2-fluoro-3-methyi-phenyl)-pyridin-2-ylamine with 4-fluoro-benzenesulfonyl chloride there was obtained: N- [5-(6-Chloro-2-fluoro-3-methyl-phenyl)-pyridin-2-yl]-4-fluoro-benzenesulfonarnide as a light-yellow solid. ISN mass spectrum, m/e: 393.1 (M-l calculated for QgHisC^NzCbS: 393).
Example 131
a) In analogy to example 1, on reaction of 5-(5-Chloro-2-methyl-phenyl)-6-methyl-pyridin-2-ylamine with 3-trifluoromethyl-benzenesulfonyl chloride there was obtained: N-[5-(5-Chloro-2-methyl-phenyl)-6-methyl-pyridin-2-yl] -3-trifluoromethyl-benzenesulfonamide as an orange oil. ISN mass spectrum, m/e: 439 (M-l calculated for : 439).
Preparation of the starting material:
b) In analogy to example Ib), on reaction of 5-bromo~6-rnethyl-pyridin-2-ylamine with 5-chloro-2-methyl-phenylboronic acid there was obtained: 5-(5-Chloro-2-methyl-phenyl)-6-methyl-pyridin-2-ylamine as a white solid. ISP mass spectrum, m/e: 233 (M+l calculated for C13Hi3ClN2:233).
Example 132
a) In analogy to example 1, on reaction of 5-(5-Chloro-2-methyl-phenyl)-6-methyl-pyridin-2-ylamine with 4-fluoro-benzenesulfonyl chloride there was obtained: N-[5-(5-Chloro-2-methyl-phenyl)-6-methyl-pyridin-2-yl] -4-fluoro-benzenesulfonamide as a white solid. ISN mass spectrum, m/e: 389 (M-l calculated for C19Hi6ClFN2O2S: 389).
Example 133
a) In analogy to example 1, on reaction of 5-(5-Chloro-2-methyl-phenyl)-6-methyl-pyridin-2-ylamine with 3-chloro-2-methyl-benzenesulfonyl chloride there was obtained:. 3-Chloro-N-[5-(5-chloro-2-methyl-phenyl)-6-methyl-pyridin-2-yl]-2-methyl-benzenesulfonamide as a white solid. ISN mass spectrum, m/e: 419 (M-l calculated for 2S: 419).
Example 134
a) In analogy to example 1, on reaction of 5-(6-Ghloro-2-fluoro-3-methyl-phenyl)-6-methyl-pyridin-2-ylamine with 3-trifluoromethyl-benzenesulfonyl chloride there was obtained: N-[5-(6-Chloro-2-fluoro-3-methyl-phenyl)-6-methyl-pyridin-2-yl]-3-
trifluoromethyl-benzenesulfonamide as a light-yellow solid. ISN mass spectrum, m/e: 457.2 (M-1 calculated for CjoHisCU^NjOjS: 457).
Preparation of the starting material
b) In analogy to example Ib), on reaction of 5-bromo -6-methyl-pyridin-2-ylaniine with 6-Chloro-2-fluoro-3-methyl-phenylboronic acid there was obtained: 5-(5-chloro-2-methyl-phenyl)-6-methyl-pyridin-2-ylamine as which was used without further purification in the next reaction step.
Example 135
In analogy to example 1, on reaction of 5-(6-Chloro-2-fluoro-3-methyl-phenyl)-6-methyl-pyridin-2-ylamine with 4-fluoro-benzenesulfonyl chloride there was obtained: N- [5-(6-CUoro-2-fluoro-3-methyl-phenyl)-6-methyl-pyridin-2-yl]-4-fluoro-benzenesulfonamide as an off-white solid. ISN mass spectrum, m/e 407.2 (M-1 calculated for Q 407).
Example 136
In analogy to example 1, on reaction of 5-(4-fluoro-2-methyl-phenyl)-pyridin-2-ylamine with 4-chloro-benzenesulfonyl chloride there was obtained: 4-Chloro-N-[5-(4-fluoro-2-methyl-phenyl)-pyridin-2-yl]-benzenesulfonamide as a white solid. ISN mass spectrum, m/e: 375.2 (M-1 calculated for CigHuClF^OjS: 375).
Example 137
In analogy to example 1, on reaction of 5-(4-fluoro-2-methyl-phenyl)-pyridin-2-ylamine with 3-chloro-benzenesulfonyl chloride there was obtained: 3-Chloro-N- [5-(4-fluoro-2-methyl-phenyl)-pyridin-2-yl]-benzenesulfonamide as a white solid. ISN mass spectrum, m/e: 375.2 (M-1 calculated for CiaHuClFNaOaS: 375).
Example 138
a) In analogy to example 1, on reaction of 5-(4-fluoro-2-methyl-phenyl)-pyridin-2-ylamine with 2,4-dichloro-5-methyl-benzenesulfonyl chloride there was obtained: 2,4-Dichloro-N- [5- (4-fluoro-2-methyl-phenyl) -pyridin-2-yl] -6-methyl-benzenesuIfonamide as a white solid. ISN mass spectrum, m/e: 422.9 (M-l calculated for 423).
Example 139
a) In analogy to example 1, on reaction of 5-(2,5-Dichloro-phenyl)-6-methyl-pyridin-2-ylamine with 3-chloro-benzenesulfonyl chloride there was obtained: 3-Chloro-N-[5-(2,5-dichloro-phenyl)-6-methyl-pyridin-2-yl]-benzenesulfbnamide as a light-yellow solid. ISN mass spectrum, m/e: 425 (M-l calculated for QgEbCk^C^S: 425).
Preparation of the starting material:
b) In analogy to example Ib), on reaction of 5-bromo -6-methyl-pyridin-2-ylamine with 2,5-dichloro-phenylboronic acid there was obtained: 5-(2,5-Dichloro-phenyl)-6-methyl-pyridin-2-ylamine as white solid. El mass spectrum, m/e: 252.1 (M calculated for Ci2H10Cl2N2: 252).
Example 140
a) In analogy to example 1, on reaction of 5-(2,5-Dichloro-phenyl)-6-methyl-pyridin-2-ylamine with 4-fluoro-benzenesulfonyl chloride there was obtained: N-[5-(2,5-Dichloro-phenyl)-6-methyl-pyridin-2-yl]-4-fluoro-benzenesulfonamide as a white solid. ISN mass spectrum, m/e: 409 (M-1 calculated for C^HnCUFNaOzS: 409).
Example 141
a) In analogy to example 1, on reaction of 5-(5-Fluoro-2-rnethyl-phenyl)-6-methyl-pyridin-2-ylamine with 3-trifluoro-benzenesulfonyl chloride there was obtained: N-[5-(5-
Huoro-2-mettyl-phenyl)-6-methyl-pyridm-2-yl]-3-trifluoromethyl-beri2enesiilfonamide as an off-white solid. ISN mass spectrum, m/e: 422.9 (M-l calculated for QoHieF^C^S: 423).
Preparation of the starting material:
b) In analogy to example Ib), on reaction of 5-bromo -6-methyl-pyridin-2-ylamine with 5-fluqro-2-methyl-phenylboronic acid there was obtained: 5-(5-Fluoro-2-methyl-phenyi)-6-methyl-pyridin-2-ylamine a light-yellow oil. El mass spectrum, m/e: 216.2 (M calculated forCi3H13FN2:216).
Example 142
a) In analogy to example 1, on reaction of 5-(5-Fluoro-2-methyl-phenyl)-6-methyl-pyridin-2-ylamine with 4-fluoro-benzenesulfonyl chloride there was obtained: 4-Fluoro-N-[5-(5-fluoro-2-metiiyl-phenyl)-6-niethyl-pyridin-2-yl]-benzenesulfonarnide as an off-white solid. ISN mass spectrum, m/e: 373.1 (M-l calculated for CwHieF^OjS: 373).
Example 143
a) In analogy to example 1, on reaction of 5-(5-Fluoro-2-methyl-phenyl)-6-methyl-pyridin-2-yiamine with 3-chloro-benzenesulfonyl chloride there was obtained: 3-Chloro-N-[5-(5-fluoro-2-methyl-phenyl)-6-methyl-pyridin-2-yl]-benzenesulfonamide as an off-white solid. ISN mass spectrum, m/e: 389 (M-l calculated for QgHieCUHSbOaS: 389).
Example 144
a) In analogy to example 1, on reaction of 5-(2,5-Dichloro-phenyl)-6-methyl-pyridin-2-ylamine with 3-trifluoromethyl-benzenesulfonyl chloride there was obtained: N-[5-(2,5-Dichloro-phenyl)-6-methyl-pyridin-2-yl]-3-trifl.uoromethyl-benzenesulfonamide as an orange oil. ISN mass spectrum, m/e: 459 (M-l calculated for CigHisCy^OaS: 459).
Example 145
a) In analogy to example 1, on reaction of 5-(2-Chloro-4-fluoro-phenyl)-6-methyl-pyridin-2-ylamine with 3-trifluoro-benzenesulfonyl chloride there was obtained: N-[5-(2-Chloro-4-fluoro-phenyl)-6-methyl-pyridin-2-yl]-3-trifluoromethyl-benzenesulfonamide as an light-yellow solid. ISN mass spectrum, m/e: 442.9 (M-l calculated for : 443).
Preparation of the starting material:
b) In analogy to example Ib), on reaction of 5-bromo-6-methyl-pyridin-2-ylamine with 2-chloro-4-fluoro-phenylboronic acid there was obtained; 5-(2-Chlorc-4-fluoro-phenyl)-6-methyl-pyridin-2-yiamine an off-white soli. El mass spectrum, m/e: 236.1 (M calculated for C12HioClFN2:236).
Example 146
In analogy to example 1, on reaction of 5-(2-Chloro-4-fluoro-phenyi)-6-methyl-pyridin-2-ylamine with 4-fluoro-benzenesulfonyl chloride there was obtained: N-[5-(2-Chloro-4-fluoro-phenyl)-6-methyl-pyridin-2-yl]-4-nuoro-benzenesulfonamide as a white solid. ISN mass spectrum, m/e: 392.9 (M-l calculated for Ci8Hi3ClF2N2O2S: 393).
Example 147
In analogy to example 1, on reaction of 5-(2-Chloro-4-nuoro-phenyl)-6-methyl-pyridin-2-ylamine with 3-chloro-benzenesulfonyl chloride there was obtained: 3-Chloro-N-[5-(2-chloro-4-fiuoro-phenyl)-6-methyl-pyridin-2-yl]-benzenesulfonamide as a white solid. ISN mass spectrum, m/e: 409 (M-l calculated for CigHi3Cl2FN2O2S: 409).
Example 148
a) In analogy to example 1, on reaction of 5-(2,3-Dichloro-phenyl)-6-methyl-pyridin-2-ylamine with 3-trifluoro-benzenesulfonyl chloride there was obtained: N-[5-(2,3-Dichloro-phenyl)-6-methyl-pyridin-2-yl] -3-trifluorometh.yl-benzenesulfonamide as a
light-yellow amorphous solid. ISN mass spectrum, m/e: 459.2 (M-1 calculated for : 459).
Preparation of the starting material:
b) In analogy to example Ib), on reaction of 5-bromo-6-methyl-pyridin-2-ylamine with 2,3-dichloro -phenylboronic acid there was obtained: 5-(2,3-Dichloro-phenyl)-6-methyl-pyridin-2-ylamine an off-white solid. El mass spectrum, m/e: 252.1 (M calculated for C12Hi0Cl2N2:252).
Example 149
a) In analogy to example 1, on reaction of 5-(2,3-DicMoro-phenyl)-6-methyl-pyridin-2-ylamine with 4-fluoro-benzenesulfbnyl chloride there was obtained: N-[5-(2,3-Dichloro-phenyl)-6-methyl-pyridin-2-yl]-4-fluoro-benzenesulfonamide as a white solid. ISN mass spectrum, m/e: 409.3 (M-1 calculated for CigHi3Cl2FN2O2S: 409).
Example 150
In analogy to example 1, on reaction of 5-(2,3-Dichloro-phenyl)-6-methyl-pyridin-2-ylamine with 3-chloro-benzenesulfonyl chloride there was obtained: 3-Chloro-N- [5-(2,3-dichloro-phenyl)-6-methyl-pyridin-2-yl]-benzenesulfonamide as a white foam. ISN mass spectrum, m/e: 425.1 (M-1 calculated for QsRbCU^OzS: 425).
Example 151
In analogy to example 1, on reaction of 5-(2,3-Dichloro-phenyl)-6-methyl-pyridin-2-ylamine with 2,4-dichloro-6-methyl-benzenesulfonyl chloride there was obtained: 2,4-Dichloro-N-[5-(2,3-dichloro-phenyl)-6-methyl-pyridui-2-yl]-6-methyl-benzenesulfonamide as an off-white foam. ISN mass spectrum, m/e: 473.1 (M-1 calculated
Example 152
In analogy to example 1, on reaction of 5-(2>3-Dicnloro-phenyl)-6-methyl-pyridin-2-ylamine with 3-methyl-benzenesulfonyl chloride there was obtained: N-[5-(2,3-Dichloro-phenyl)-6-methyl-pyridin-2-yi]-3-methyl-benzenesulfonamide as a white foam. ISN mass spectrum, m/e: 405.3 (M-1 calculated for QgHigCkNaC^S: 405).
Example 153
a) In analogy to example 1, on reaction of 5-(2,5-Dichloro-phenyl)-6-methyl-pyridin-2-ylamine with 2,4-dichloro-6-methyl-benzenesulfonyl chloride there was obtained: 2,4-Dichloro-N- [5-(2,5-dichloro-phenyl)-6-methyl-pyridin-2-yl] -6-methyl-benzenesulfonamide as a light-yellow foam. ISN mass spectrum, m/e: 475 (M-1 calculated for QgHuCUFsNaOjS: 475).
Example 154
In analogy to example 1, on reaction of 5-(2-Chloro-4-fluoro-phenyl)-6-methyl-pyridin-2-ylamine with 3-methyl-benzenesulfonyl chloride there was obtained: N-[5-(2-Chloro-4-fluoro-phenyl)-6-methyl-pyridin-2-yl]-3-methyl-benzenesulfonamide as a white foam. ISN mass spectrum, m/e: 389 (M-1 calculated for CigHieClF^CbS: 389).
Example 155
In analogy to example 1, on reaction of 5-(2-Chloro-4-fluoro-phenyl)-6-methyl-pyridin-2-ylamine with 2,4-dichloro-5-methyl-benzenesulfonyl chloride there was obtained: 2,4-Dichloro-N-[5-(2-chloro-4-fluoro-phenyl)-6-methyl-pyridin-2-yl]-6-methyl-benzenesulfonamide as a white foam. ISN mass spectrum, m/e: 457.1 (M-1 calculated for C19H14Cl3FN202S:457).
Example 156
In analogy to example 1, on reaction of 5-(2,4-bis-trifluoromethyl-phenyl)-pyridin-2-ylamine with 3-chloro-benzenesulfonyl chloride there was obtained: N-[5-(2,4-Bis-trifluoromethyl-phenyl)-pyridin-2-yl]-3-chloro-benzenesulfonamide as a white solid. ISN mass spectrum, m/e: 479 (M-1 calculated for Ci9HiiClF6N2O2S: 479).
Example 157
In analogy to example 1, on reaction of 5-(2,4-bis-trifluoromethyl-phenyl)-pyridin-2-ylamine with 3-methyl-benzenesulfonyl chloride there was obtained: N-[5-(2,4-Bis-trifluoromethy!-phenyl)-pyridin-2-yl]-3-methyl-benzenesulfonamide as a white solid. ISN mass spectrum, m/e: 459.1 (M-1 calculated for C2oHi4F6N2O2S: 459).
Example 158
In analogy to example 1, on reaction of 5-(2,4-bis-trifluoromethyl-phenyi)-pyridin-2-ylamine with 4-fluoro-benzenesulfonyi chloride there was obtained: N-[5-(2,4-Bis-trifluoromethyl-phenyl)-pyridin-2-yi]-4-fluoro-benzenesulfonamide as a white foam. ISN mass spectrum, m/e: 463 (M-1 calculated for C^oHnFy^C^S: 463).
Example 159
In analogy to example 1, on reaction of 5-(2^-Dichloro-phenyl)-6-methyl-pyridin-2-ylamine with 4-fluoro-3-trifluoro-benzenesulfonyl chloride there was obtained: N-[5-(2,3-Dichloro-phenyl)-6-methyl-pyridin-2-yli-4-rluoro-3-trifluoromethyl-benzenesulfonamide as an off-white foam. ISN mass spectrum, m/e: 476.9 (M-1 calculated for Ci9Hi2Cl2F4N2O2S: 477).
Example 160
In analogy to example 1, on reaction of 5-(2,3-Dichloro-phenyl)-6-methyl-pyridin-2-ylamine with 3-chIoro-4-fluoro-benzenesulfonyl chloride there was obtained: 3-Chloro-N-[5-(2,3-dichloro-phenyl)-6-methyl-pyridin-2-yl]-4-fluoro-benzenesulfonamide as an off-white foam. ISN mass spectrum, m/e: 442.9 (M-1 calculated for CigHuCHFNzC^S: 443).
Example 161
a) In analogy to example 1, on reaction of 5-(2-Huoro-phenyl)-6-methyl-pyridin-2-
ylamine with 3-chloro-benzenesulfonyl chloride there was obtained: 3-Chloro-N-[5-(2-
fluoro-phenyl)-6-methyl-pyridin-2-yl]-benzenesulfonamide as an off-white foam. ISN
mass spectrum, m/e: 375.2 (M-1 calculated for QgHuClFN^S: 375).
Preparation of the starting material:
b) In analogy to example Ib), on reaction of 5-bromo-6-methyl-pyridm-2-ylamine with 2-
fluoro-phenylboronic acid there was obtained: -(2-Flu6ro-phenyl)-6-methyl-pyridin-2-
ylamine an off-white solid. El mass spectrum, m/e: 202.2(M calculated for Ci2HnFN2:
202).
Example 162
a) In analogy to example 1, on reaction of 5-(2-Fluoro-phenyl)-6-methyl-pyridin-2-ylamine with 4-fluoro-benzenesulfonyl chloride there was obtained: 4-Fluoro-N-[5-(2-fluoro-phenyl)-6-methyl-pyridin-2-yl]-benzenesulfonamide as a white foam. ISN mass spectrum, m/e: 359 (M-1 calculated for dgHuFz^C^S: 359).
Example 163
a) In analogy to example 1, on reaction of 5-(2-Fluoro-phenyl)-6-methyl-pyridin-2-ylamine with 4-fluoro-3-trifluoromethyl-benzenesulfonyl chloride there was obtained: 4-Fluoro-N-[5-(2-fluoro-phenyl)-6-methyl-pyridin-2-yl]-3-trifluoromethyl-benzenesulfonamide as a white foam. ISN mass spectrum, m/e: 427.1 (M-1 calculated for Ci9Hi3F5N202S: 427).
Example 164
In analogy to example 1, on reaction of 5-(2,4-bis-trinuoromethyl-phenyl)-pyridin-2-ylamine with 3-chloro-4-fl.uoro-benzenesulfonyl chloride there was obtained: N-[5-(2,4-Bis-trifluoromethyl-phenyl)-pyridin-2-yl]-3-chloro-4-fIuoro-benzenesulfonamideas an off-white foam. ISN mass spectrum, m/e: 496.9 (M-1 calculated for Ci9Hi0ClF7N2O2S: 497)
Example 165
n analogy to example 1, on reaction of 5-(2-Huoro-phenyl)-6-methyl-pyridin-2-ylamine vith 2,4-dichloro-6-rnethyl-3-benzenesulfonyl chloride there was obtained: 2,4-Dichloro-4-[5-(2-fluoro-phenyl)-6-methyl-pyriclin-2-yl]-6-methyl-benzenesulfonarnide as an off-diite foam. ISN mass spectrum, m/e: 422.9 (M-l calculated for Ci9Hi5Cl2FN2O2S: 423).
Example 166
n analogy to example 1, on reaction of 5-(2-Fluoro-phenyl)-6-me'thyl-pyridin-2-ylamine rith 3-trifluoromethyl-benzenesulfonyl chloride there was obtained: N-[5-(2-Fluoro-henyl)-6-methyl-pyridin-2-yl]-3-trifluoromethyl-benzenesulfonamide as a light-yellow aam. ISN mass spectrum, m/e: 409.1 (M-l calculated for QgH^NjOaS: 409).
Example 167
) In analogy to example 1, on reaction of 5-(2-Chloro-phenyl)-3,4-dimethyl-pyridin-2-lamine with 3-trifluoro-benzenesulfonyl chloride there was obtained: N-[5-(2-Chloro-henyl)-3,4-dimethyl-pyridin-2-yl]-3-trifluoromethyl-benzenesulfonamide as a yellow norphous solid. ISN mass spectrum, m/e: 439.1 (M-l calculated for C2oH16ClF3N2O2S: J9).
reparation of the starting material:
I In analogy to example Ib), on reaction of 5-bromo-3,4-dimethyl-pyridin-2-ylamine ith 2-chloro-phenylboronic acid there was obtained: 5-(2-Chloro-phenyl)-3,4-dimetLyl-Tidin-2-ylamine a white solid. ISP mass spectrum, m/e: 233 (M+l calculated for 13H13C1N2: 233).
Example 168
In analogy to example 1, on reaction of 5-(2-Chloro-phenyl)-3,4-dimethyl-pyridin-2-imine with. 3-chloro-benzenesulfonyl chloride there was obtained: 3-Chloro-N-[5-(2-loro-phenyl)-3,4-dimethyl-pyridin-2-yl]-benzenesulfonamide as a yellow amorphous lid. ISN mass spectrum, m/e: 405.1 (M-l calculated for Ci9H16Cl2N2O2S: 405).
Example 169
In analogy to example 1, on reaction of 5-(2-Chloro-phenyl)-3,4-dimethyl-pyridin-2-ylamine with 4-fluoro-benzenesulfonyl chloride there was obtained: N-[5-(2-Chloro-phenyl)-3,4-dimethyl-pyridin-2-yl)-4-fluoro-benzenesulfonaniide as a yellow amorphous solid. ISN mass spectrum, rn/e: 389 (M-l calculated for Ci9Hi6ClFN2O2S: 389).
Example 170
a) In analogy to example 1, on reaction of 2-Methyl-[3,3']bipyridmyl-6-ylaminewith 3-trifluoro-benzenesulfonyl chloride there was obtained: N-(2-Methyl-[3,3']bipyridinyl-6-yl)-3-trifluoromethyl-benzenesulfonamide as a light-yellow amorphous solid. ISN mass spectrum, m/e: 392(M-1 calculated for CigHuFsNsOaS: 392).
Preparation of the starting material:
b) In.analogy to example Ib), on reaction of 5-bromo-6-methyl-pyridin-2-ylamine with 3-pyridylboronic acid there was obtained: 2-Methyl-[3,3']bipyridinyl-6-ylamine a yellow solid. El mass spectrum, m/e: 185.2 (M calculated for CnHnN3:185).
Example 171
a) In analogy to example 1, on reaction of 5-(2-Chloro-phenyl)-4-methyl-pyridin-2-ylamine with 3-chloro-benzenesulfonyl chloride there was obtained: 3-Chloro-N-[5-(2-chloro-phenyl)-4-methyl-pyridin-2-yl]-benzenesulfonamide as a white solid. ISN mass spectrum, m/e: 391 (M-l calculated for QgHuCy^CbS: 391).
Preparation of the starting material:
b) In analogy to example Ib), on reaction of 5-bromo-4-methyl-pyridin-2-ylamine with 2-chloro-phenylboronic acid there was obtained: 5-(2-Chloro-phenyi)-4-methyl-pyridin-2-ylamine a yellow solid. El mass spectrum, m/e: 218.1 (M calculated for CnHnClN2: 218).
xample 172
a) In analogy to example 1, on reaction of 5-(2-Chloro-phenyl)-4-methyl-pyridin-2-ylamine with 3-trifluoromethyl-benzenesulfonyl chloride there was obtained: N-[5-(2-Chloro-phenyl)-4-methyl-pyridin-2-yl]-3-trifluoromethyl-benzenesulfonamide as an off-white solid. ISN mass spectrum, m/e: 425.1 (M-1 calculated for C^HuClFs^OaS: 425).
a) In analogy to example 1, on reaction of 5-(2-Chloro-phenyl)-4-methyl-pyridin-2-ylamine wtb^>4-dichloro-6-methyl-benzenesulfonyl chloride there was obtained: 2,4--OicWoro-N-[5-(2-cUoro-phenyl)-4-mettyi-pyridin-2-yl]-6-me&yi-benzenesulfonamide as a white solid. ISN mass spectrum, m/e: 439 (M-1 calculated for Q^isCM^OzS: 439).
Example 174
In analogy to example 1, on reaction of 2-Methyl-[3,3']bipyridinyl-6-ylamine with 3-chloro-benzenesulfonyl chloride there was obtained: 3-Chloro-N-(2-methyl-[3,3']bipyridinyl-6-yl)-benzenesulfonainide as a light-brown amorphous solid. ISN mass spectrum, m/e: 358 (M-1 calculated for CnHuClNsOzS: 358).
Example 175
In analogy to example 1, on reaction of 5-(4-Fluoro-2-methyl-phenyl)-4-methyl-pvri(.l)i; 2-ylamine with 3-chloro-benzenesulfonyl chloride there was obtained: 3-Chloro-N ;' (4 fluoro-2-methyl-phenyl)-4-methyl-pyridin-2-yl]-benzenesulfonamide as a cdorless soi;. ISN mass spectrum, m/e: 389 (M-1 calculated for CigHClFOzS: 389).
Preparation of the starting material:
b) In analogy to example Ib), on reaction of 5-bromo-4-meLhy! pYndin-2-ylamim v/ith 2-chloro-phenylboronic acid there was obtained: 5-(4-Fluoro .?- ruediyi- phenyl)-4 ,rieth~ f
pyridin-2-ylamine as an amorphous light-yellow solid. ISP mass spectrum, m/e: 217.3 (M+l calculated for C13Hi3FN2:217).
Example 176
a) In analogy to example 1, on reaction of 5-(4-Fluoro-2-methyl-phenyl)-4-rnethyl-pyridin-2-ylamine with 3-trifluoromethyl-benzenesulfonyl chloride there was obtained; N-[5-(4-Fluoro-2-methyl-phenyl)-4-methyl-pyridin-2-yl]-3-triiluoromethyl-benzenesulfonamide as a white solid, ISN mass spectrum, m/e: 423 (M-l calculated for C2oH16F4N202S:423).
Example 177
a) In analogy to example 1, on reaction of 5-(4-Fluoro-2-rnethyl-phenyl)-4-methyl-pyridin-2-ylamine with 2,4-dichloro-6-methyl-trifluoromethyl-benzenesulfonyl chloride there was obtained: 2,4-Dichloro-N-[5-(4-fl.uoro-2-meth.yl-phenyl)-4-metJiyl-pyridin-2-yl]-6-methyl-benzenesulfonamide as a white solid. ISN mass spectrum, m/e: 437.2(M-1 calculated for CaoHnCkFtyOaS: 437).
Example A
A compound of formula I can be used in a manner known per se as the active ingredient for the production of tablets of the following composition:
Per tablet
Active ingredient 200 mg
Microcrystalline cellulose 155mg
Corn starch 25 mg
Talc 25 mg
Hydroxypropylmethylcellulose 20 mg
425 mg
Example B
A compound of formula I can be used in a manner known per se as the active ingredient for the production of capsules of the following composition:
Per capsule
Active ingredient 100.0 mg
Corn starch 20.0 mg
Lactose 95.0 mg
Talc 4.5 mg
Magnesium stearate 0.5 mg
220.0 mg




We claim:
1. Aryl-pyridine compounds of formula (I)
(Formula Removed)
and pharmaceutically acceptable salts and esters thereof wherein
R1 is hydrogen, alkyl, cycloalkyl, hydroxy, hydroxyalkyl, alkoxy, alkoxyalkyl, amino
or aminoalkyl;
R2 is hydrogen, alkyl or halogen;
R3 is hydrogen, alkyl or halogen;
R4 is phenyl, naphtyl, thiophenyl, pyridyl, quinolyl, piperidyl, morpholyl or
thiomorpholyl optionally substituted with one or more substituents independently
selected from alkyl, cycloalkyl, halogen, hydroxy, hydroxyalkyl, alkoxy, alkoxyalkyl,
hydroxyalkoxy, alkoxyalkoxy, cyano, trifluoromethyl, trifluoromethoxy, aryl, arylalkyl,
aryloxy, heterocyclyl, alkylcarbonylamino, alkoxycarbonylalkoxy and alkyl-SO2-;
R5 is hydrogen or alkyl;
R6,R7,R8,R9and R10 are independently selected from hydrogen, alkyl, halogen, cyano,
trifluoromethyl, alkoxy and alkyl-SO2-;
A is nitrogen or C-R10;
E is nitrogen or C-R9;
G is nitrogen or C-R8;
wherein not more than one of A, E and G is nitrogen, wherein
- the term "alkyl", alone or in combination, signifies a straight-chain or branched-chain alkyl group with 1 to 8 carbon atoms,
- the term "cycloalkyl", alone or in combination, signifies a cycloalkyl ring with 3 to 8 carbon atoms,
- the term "aryl", alone or in combination, signifies a phenyl or naphthyl group,
- the term "heterocyclyl", alone or in combination signifies a saturated, partially unsaturated or aromatic 5- to 10-membered heterocycle which contains one or more hetero atoms selected from nitrogen, oxygen and sulphur,
- the term "amino", alone or in combination, signifies a primary, secondary or tertiary amino group bonded via the nitrogen atom, with the secondary amino group carrying an alkyl or cycloalkyl substituent and the tertiary amino group carrying two similar or different alkyl or cycloalkyl substituents or the two nitrogen substituents together forming a ring.

2. The compounds as claimed in claim 1, wherein R1 is hydrogen.
3. The compounds as claimed in claim 1, wherein R1 is C1-C8 alkyl.
4. The compounds as claimed in any one of claims 1 to 3, wherein R2 is hydrogen.
5. The compounds as claimed in any one of claims 1 to 3, wherein R2 is C1-C8 alkyl.
6. The compounds as claimed in any one of claims 1 to 5, wherein R3 is hydrogen.
7. The compounds as claimed in any one of claims 1 to 6, wherein R3 is C1-C8 alkyl.
8. The compounds as claimed in any one of claims 1 to 7, wherein R5 is hydrogen.
9. The compounds as claimed in any one of claims 1 to 8, wherein A is C-R10.
10. The compounds as claimed in any one of claims 1 to 9, wherein E is C-R9.
11. The compounds as claimed in any one of claims 1 to 9, wherein E is nitrogen.
12. The compounds as claimed in any one of claims 1 to 11, wherein G is C-R8.
13. The compounds as claimed in any one of claims 1 to 12, wherein R4 is phenyl optionally substituted with one to three substituents independently selected from alkyl, cycloalkyl, halogen, hydroxy, hydroxyalkyl, alkoxy, alkoxyalkyl, hydroxyalkoxy, alkoxyalkoxy, cyano, trifluoromethyl, trifluoromethoxy, aryl, arylalkyl, aryloxy, heterocyclyl, alkylcarbonylamino, alkoxycarbonylalkoxy and alkyl-SO2- and wherein the terms alkyl, cycloalkyl, aryl, amino and heterocyclyl are defined as in claim 1.
14. The compounds as claimed in claim 13, wherein R4 is phenyl substituted with one to three substituents independently selected from C1-C8 alkyl, halogen and trifluoromethyl.
15. The compounds as claimed in any one of claims 1 to 14, wherein R6 , R7 , R8 , R9 and R10 are independently selected from hydrogen, C1-C8 alkyl, halogen and trifluoromethyl.
16. The compounds as claimed in any one of claims 1 to 15 selected from
N-[5-(2-Chloro-phenyl)-pyridin-2-yl]-5-fluoro-2-methyl-benzenesulfonamide;
3-Chloro-N-[5-(2-chloro-phenyl)-pyridin-2-yl]-2-methyl-benzenesulfonamide;
N-[5-(2,4-Dichloro-phenyl)-pyridin-2-yl]-5-fluoro-2-methyl-benzenesulfonamide;
3-Chloro-N-[5-(2,4-dichloro-phenyl)-pyridin-2-yl]-2-methyl-benzenesulfonamide;
3-Chloro-N-[5-(2-chloro-phenyl)-6-methyl-pyridin-2-yl]-2-methyl-
benzenesulfonamide;
Biphenyl-4-sulfonic acid [5-(2-chloro-phenyl)-6-methyl-pyridin-2-yl]-amide;
3-Chloro-N-[5-(2-chloro-4-fluoro-phenyl)-pyridin-2-yl]-2-methyl-benzenesulfonamide;
3-Chloro-N-[5-(3-fluoro-phenyl)-pyridin-2-yl]-2-methyl-benzenesulfonamide;
3-Chloro-N-[5-(2,4-difluoro-phenyl)-pyridin-2-yl]-2-methyl-benzenesulfonarnide;
N-[5-(2,4-Difluoro-phenyl)-pyridin-2-yl]-5-fluoro-2-methyl-benzenesulfonamide;
3-Chloro-N-[5-(4-methoxy-phenyl)-pyridin-2-yl]-2-methyl-benzenesulfonamide;
3-Chloro-N-[5-(4-fluoro-phenyl)-pyridin-2-yl]-2-methyl-benzenesulfonamide;
5-Fluoro-N-[5-(4-fluoro-phenyl)-pyridin-2-yl]-2-methyl-benzenesulfonamide;
5-Fluoro-N-[5-(2-methoxy-phenyl)-pyridin-2-yl]-2-methyl-benzenesulfonamide;
3-Chloro-N-[5-(2-fluoro-phenyl)-pyridin-2-yl]-2-methyl-benzenesulfonamide;
5-Fluoro-N-[5-(2-fluoro-phenyl)-pyridin-2-yl]-2-methyl-benzenesulfonamide;
2,4-Dichloro-N-[5-(2-chloro-phenyl)-pyridin-2-yl]-6-methyl-benzenesulfonamide;
N-[5-(2-Chloro-phenyl)-pyridin-2-yl]-2,5-difluoro-benzenesulfonamide;
3-Chloro-N-[5-(4-methanesulfonyl-phenyl)-pyridin-2-yl]-2-methyl-
benzenesulfonamide;
3-Chloro-N-[5-(4-fluoro-phenyl)-6-methyl-pyridin-2-yl]-2-methyl-
benzenesulfonamide;
5-Fluoro-N-[5-(4-fluoro-phenyl)-6-methyl-pyridin-2-yl]-2-methyl-
benzenesulfonamide;
3-Chloro-N-[5-(3-fluoro-phenyl)-6-methyl-pyridin-2-yl]-2-methyl-
benzenesulfonamide;
5-Fluoro-N-[5-(3-fluoro-phenyl)-6-methyl-pyridin-2-yl]-2-methyl-
benzenesulfonamide;
N-[5-(2,4-Dichloro-phenyl)-pyridin-2-yl]-3,4-dimethoxy-benzenesulfonamide;
3,4-Dichloro-N-[5-(2,4-dichloro-phenyl)-pyridin-2-yl]-benzenesulfonamide;
N-[5-(2,3-Dichloro-phenyl)-pyridin-2-yl]-2,5-difluoro-benzenesulfonamide;
3-Chloro-N-[5-(23-dichloro-phenyl)-pyridin-2-yl]-2-methyl-benzenesulfonamide;
3,4-Dichloro-N-[5-(2-chloro-phenyl)-pyridin-2-yl]-benzenesulfonamide;
N- [5-(2-Chloro-phenyl)-pyridin-2-yl] -3,4-dimethoxy-benzenesulfonamide;
3-Chloro-N-[5-(2-chloro-phenyl)-pyridin-2-yl]-4-methyl-benzenesulfonamide;
5-Fluoro-N-[5-(4-fluoro-2-methyl-phenyl)-pyridin-2-yl]-2-methyl-
benzenesulfonamide;
3-Chloro-N-[5-(4-fluoro-2-methyl-phenyl)-pyridin-2-yl]-2-methyl-
benzenesulfonamide;
3-Chloro-N-[5-(2-chloro-phenyl)-pyridin-2-yl]-4-methoxy-benzenesulfonamide;
4,5-Dichloro-N-[5-(2-chloro-phenyl)-pyridin-2-yl]-2-fluoro-benzenesulfonamide;
3-Chloro-N-[5-(2,4-dichloro-phenyl)-pyridin-2-yl]-4-methoxy-benzenesulfonamide;
3-Chloro-N-[5-(2,4-dichloro-phenyl)-pyridin-2-yl]-4-methyl-benzenesulfonamide;
Piperidine-1-sulfonic acid [5-(2,4-dichloro-phenyl)-pyridin-2-yl]-amide;
N-[5-(2,3-Dichloro-phenyl)-pyridin-2-yl]-2-trifiuoromethyl-benzenesulfonamide;
N-[5-(2,3-Dichloro-phenyl)-pyridin-2-yl]-4-fluoro-benzenesulfonamide;
N-[5-(2,5-Dichloro-phenyl)-pyridin-2-yl]-2,5-difluoro-benzenesiilfonamide;
N-[5-(2,5-Dichloro-phenyl)-pyridin-2-yl]-5-fluoro-2-methyl-benzenesulfonamide;
3-Chloro-N-[5-(2,5-dichloro-phenyl)-pyridin-2-yl]-2-methyl-benzenesulfonamide;
5-Fluoro-N-[5-(2-fluoro-5-trifluoromethyl-phenyl)-pyridin-2-yl]-2-methyl-
benzenesulfonamide;
3-Chloro-N-[5-(2-fluoro-5-trifluoromethyl-phenyl)-pyridin-2-yl]-2-methyl-
benzenesulfonamide;
3-Chloro-2-methyl-N-[5-(2-trifluoromethyl-phenyl)-pyridin-2-yl]-benzenesulfonamide;
3-Chloro-4-methyl-N-[5-(2-trifluoromethyl-phenyl)-pyridin-2-yl]-benzenesulfonantide;
5-Chloro-N-[5-(2,4-dichloro-phenyl)-pyridin-2-yl]-2-methoxy-benzenesulfonamide;
N-{2-Chloro-4-[5-(2,4-dichloro-phenyl)-pyridin-2-ylsulfamoyl]-phenyl}-acetamide;
N-[5-(2,4-Dichloro-phenyl)-pyridin-2-yl]-4-trifluoromethyl-benzenesulfonamide;
N-[5-(2,4-Dichloro-phenyl)-pyridin-2-yl]-4-methysulfonyl-benzenesulfonamide;
3-Chloro-N-[5-(2,3-difluoro-phenyl)-pyridin-2-yl]-4-methyl-benzenesulfonamide;
N-[5-(2,3-Difluoro-phenyl)-pyridin-2-yl]-5-fluoro-2-methyl-benzenesulfonamide;
N-[5-(2,4-Bis-trifluoromethyl-phenyl)-pyridin-2-yl]-3-chloro-2-methyl-
benzenesulfonamide;
N-[5-(2,4-Bis-trifluoromethyl-phenyl)-pyridin-2-yl]-3-chloro-4-methyl-
benzenesulfonamide;
3-Chloro-N-[5-(2,3-difluoro-phenyl)-pyridin-2-yl]-2-methyl-benzenesulfonamide;
Piperidine-1-sulfonic acid [5-(2,3-dichloro-phenyl)-pyridin-2-yl]-amide;
5-Chloro-N-[5-(4-fluoro-phenyl)-6-methyl-pyridin-2-yl]-2-methoxy-
benzenesulfonamide;
N-{2-Chloro-4-[5-(4-fluoro-phenyl)-6-methyl-pyridin-2-ylsulfamoyl]-phenyl}-
acetamide;
N-[5-(4-Fluoro-phenyl)-6-methyl-pyridin-2-yl]-4-trifluoromethyl-benzenesulfonamide;
N-[5-(4-Fluoro-phenyl)-6-methyl-pyridin-2-yl]-4-methanesulfonyl-
benzenesulfonamide;
{4-[5-(2,3-Dichloro-phenyl)-pyridin-2-ylsulfamoyl]-phenoxy}-acetic acid methyl ester;
N-[5-(4-Fluoro-phenyl)-6-methyl-pyridin-2-yl]-4-trifluoromethoxy-
benzenesulfonamide;
3-Chloro-N-[5-(4-fluoro-phenyl)-6-methyl-pyridin-2-yl]-4-methoxy-
benzenesulfonamide;
4-Chloro-N-[5-(4-fluoro-phenyl)-6-methyl-pyridin-2-yl]-2,5-dimethyl-
benzenesulfonamide;
N-[5-(2,3-Dichloro-phenyl)-pyridin-2-yl]-4-(2-hydroxy-ethoxy)-benzenesulfonamide;
N-[5-(2-Chloro-phenyl)-6-methyl-pyridin-2-yl]-4-fluoro-benzenesulfonamide;
3-Chloro-N-[5-(2-chloro-phenyl)-6-methyl-pyridin-2-yl]-4-methyl-
benzenesulfonamide;
4-Chloro-N-[5-(2-chloro-phenyl)-6-methyl-pyridin-2-yl]-benzenesulfonamide;
2,4-Dichloro-N-[5-(2-chloro-phenyl)-6-methyl-pyridin-2-yl]-6-methyl-
benzenesulfonamide;
Piperidine-1 -sulfonic acid [5-(2-chloro-phenyl)-6-methyl-pyridin-2-yl]-amide;
N-[5-(2,4-Dichloro-phenyl)-pyridin-2-yl]-4-fiuoro-benzenesulfonamide;
4-Chloro-N-[5-(2,4-dichloro-phenyl)-pyridin-2-yl]-2,5-dimethyl-benzenesulfonamide;
N-[5-(2,4-Dichloro-phenyl)-pyridin-2-yl]-2,4-difluoro-benzenesulfonamide;
2,4-Dichloro-N-[5-(2,4-dichloro-phenyl)-pyridin-2-yl] -5-methyl-benzenesulfonamide;
N- [5-(2,3 -Dichloro-phenyl)-pyridin-2-yl] -3 -trifluoromethyl-benzenesulfonamide
4-Fluoro-N-[5-(4-fiuoro-2-methyl-phenyl)-6-methyl-pyridin-2-yl]-
benzenesulfonamide;
3-Chloro-N-[5-(4-fluoro-2-methyl-phenyl)-6-methyl-pyridin-2-yl]-2-methyl-
benzenesulfonamide;
5-Fluoro-N-[5-(4-fluoro-2-methyl-phenyl)-6-methyl-pyridin-2-yl]-2-methyl-
benzenesulfonamide;
3-Chloro-N-[5-(23-dichloro-phenyl)-pyridin-2-yl]-4-methyl-benzenesulfonamide;
N- [5-(2,3 -Dichloro-phenyl)-pyridin-2-yl] -4-trifluoromethyl-benzenesulfonamide;
3-Chloro-N-[5-(4-fluoro-2-methyl-phenyl)-pyridin-2-yl]-4-methyl-
benzenesulfonamide;
N-[5-(4-Fluoro-2-methyl-phenyl)-pyridin-2-yl]-3-trifluoromethyl-benzenesulfonamide;
N-[5-(4-Fluoro-2-methyl-phenyl)-pyridin-2-yl]-4-trifluoromethyl-benzenesulfonamide;
N-[5-(2-Chloro-phenyl)-pyridin-2-yl]-3-trifluoromethyl-benzenesulfonamide;
N- [5-(2-Chloro-phenyl)-pyridin-2-yl] -4-ethyl-benzenesulfonamide;
3-Chloro-N-[5-(2-chloro-phenyl)-pyridin-2-yl]-benzenesulfonamide;
3-Chloro-N-[5-(2,4-dichloro-phenyl)-pyridin-2-yl]-4-fluoro-benzenesulfonamide;
N- [5-(2,4-Dichloro-phenyl)-pyridin-2-yl] -4-ethyl-benzenesulfonamide;
N-[5-(2,4-Dichloro-phenyl)-pyridin-2-yl]-3-trifluoromethyl-benzenesulfonamide;
N-[5-(2-Chloro-phenyl)-6-methyl-pyridin-2-yl]-3-trifluoromethyl-benzenesulfonamide;
N-[5-(2-Chloro-phenyl)-6-methyl-pyridin-2-yl]-4-trifluoromethoxy-
benzenesulfonamide;
N-[5-(2-Chloro-phenyl)-pyridin-2-yl]-4-fluoro-benzenesulfonamide;
N-[5-(2-Chloro-phenyl)-pyridin-2-yl]-2,4-difluoro-benzenesulfonamide;
4-Chloro-N-[5-(2-chloro-phenyl)-pyridin-2-yl]-2,5-dimethyl-benzenesulfonamide;
4-Chloro-N-[5-(2-chloro-phenyl)-6-methyl-pyridin-2-yl]-2,5-dimethyl-
benzenesulfonamide;
N-[5-(2-Chloro-phenyl)-6-methyl-pyridin-2-yl]-2,4-difluoro-benzenesulfonamide;
3,5-Dichloro-N-[5-(2-chloro-phenyl)-6-methyl-pyridin-2-yl]-benzenesulfonainide;
N-[5-(2,4-Dichloro-phenyl)-6-methyl-pyridin-2-yl]-3-trifluoromethyl-
benzenesulfonamide;
N-[5-(2,4-Dichloro-phenyl)-6-methyl-pyridin-2-yl]-4-fluoro-benzenesulfonamide;
N-[5-(2,4-Dichloro-phenyl)-6-methyl-pyridin-2-yl]-2,4-difluoro-benzenesulfonamide;
4-Chloro-N-[5-(2,4-dichloro-phenyl)-6-methyl-pyridin-2-yl]-2,5-dimethyl-
benzenesulfonamide;
2,4-Dichloro-N-[5-(2,4-dichloro-phenyl)-pyridin-2-yl]-6-methyl-benzenesulfonamide;
3-Chloro-N-[5-(2,4-dichloro-phenyl)-pyridin-2-yl]-benzenesulfonamide;
4-Chloro-N[5-(2,4-dichloro-phenyl)-pyridin-2-yl]-benzenesulfonamide;
N-[5-(2-Chloro-phenyl)-6-methyl-pyridin-2-yl]-3-fluoro-benzenesulfonamide;
3-Chloro-N-[5-(2-chloro-phenyl)-6-methyl-pyridin-2-yl]-benzenesulfonamide;
2,4-Dichloro-N-[5-(2-chloro-phenyl)-6-methyl-pyridin-2-yl]-benzenesulfonamide;
2,4-Dichloro-N-[5-(2-chloro-phenyl)-6-methyl-pyridin-2-yl]-5-methyl-
benzenesulfonamide;
N-[5-(4-Fluoro-2-methyl-phenyl)-6-methyl-pyridin-2-yl]-3-trifluoromethyl-
benzenesulfonamide;
2,4-Dichloro-N-[5-(4-fluoro-2-methyl-phenyl)-6-methyl-pyridin-2-yl]-6-methyl-
benzenesulfonamide;
3 -Chloro-N- [5-(4-fluoro-2-methyl-phenyl)-6-methyl-pyridin-2-yl] -
benzenesulfonamide;
4-Chloro-N-[5-(4-fluoro-2-methyl-phenyl)-6-methyl-pyridin-2-yl]-
benzenesulfonamide;
N-[5-(4-Fluoro-2-methyl-phenyl)-6-methyl-pyridin-2-yl]-4-trifluoromethoxy-
benzenesulfonamide;
N-[5-(4-Fluoro-2-methyl-phenyl)-6-methyl-pyridin-2-yl]-3-methyl-
benzenesulfonamide;
2-Chloro-N-[5-(4-fluoro-2-methyl-phenyl)-6-methyl-pyridin-2-yl]-5-trifluoromethyl-
benzenesulfonamide;
4-Fluoro-N-[5-(4-fluoro-2-methyl-phenyl)-6-methyl-pyridin-2-yl]-3-trifluoromethyl-
benzenesulfonamide;
N-[5-(2-Chloro-phenyl)-6-methyl-pyridin-2-yl]-3-methyl-benzenesulfonamide;
3-Chloro-N-(2-chloro-phenyl)-6-methyl-pyridin-2-yl]-4-fluoro-benzenesulfonamide;
2-Chloro-N-[5-(2-chloro-phenyl)-6-methyl-pyridin-2-yl]-5-trifluoromethyl-
benzenesulfonamide;
N-[5-(2-Chloro-phenyl)-6-methyl-pyridin-2-yl]-4-fluoro-3-trifluoromethyl-
benzenesulfonamide;
N-[5-(2,3-Dichloro-phenyl)-pyridin-2-yl]-3-fluoro-4-methyl-benzenesulfonamide;
N-[5-(2,3-Dichloro-phenyl)-pyridin-2-yl]-3,5-dimethyl-benzenesulfonzmide;
N-[5-(5-Fluoro-2-methyl-phenyl)-pyridin-2-yl]-3-trifluoromethyl-benzenesulfonamide;
4-Fluoro-N-[5-(5-fiuoro-2-methyl-phenyl)-pyridin-2-yl]-benzenesulfonamide;
3-Chloro-N-[5-(5-fluoro-2-methyl-phenyl)-pyridin-2-yl]-2-methyl-
benzenesulfonamide;
N-[5-(5-Chloro-2-methyl-phenyl)-pyridin-2-yl]-3-trifluoromethyl-benzenesulfonamide;
N-[5-(5-Chloro-2-methyl-phenyl)-pyridin-2-yl]-4-fluoro-benzenesulfonamide;
3-Chloro-N-[5-(5-chloro-2-methyl-phenyl)-pyridin-2-yl]-2-methyl-
benzenesulfonamide;
3-Chloro-N-[5-(6-chloro-2-fluoro-3-methyl-phenyl)-pyridin-2-yl]-2-methyl-
benzenesulfonamide;
N-[5-(6-Chloro-2-fluoro-3-methyl-phenyl)-pyridin-2-yl]-3-trifiuoromethyl-
benzenesulfonamide;
N-[5-(6-Chloro-2-fluoro-3-methyl-phenyl)-pyridin-2-yl]-4-fluoro-benzenesulfonamide;
N-[5-(5-Chloro-2-methyl-phenyl)-6-methyl-pyridin-2-yl]-3-trifluoromethyl-
benzenesulfonamide;
N-[5-(5-Chloro-2-methyl-phenyl)-6-methyl-pyridin-2-yl]-4-fluoro-
benzenesulfonamide;
3-Chloro-N-[5-(5-chloro-2-methyl-phenyl)-6-methyl-pyridin-2-yl]-2-methyl-
benzenesulfonamide;
N-[5-(6-Chloro-2-fluoro-3-methyl-phenyl)-6-methyl-pyridin-2-yl]-3-trifluoromethyl-
benzenesulfonamide;
N-[5-(6-Chloro-2-fluoro-3-methyl-phenyl)-6-methyl-pyridin-2-yl]-4-fluoro-
benzenesulfonamide;
4-Chloro-N-[5-(4-fluoro-2-methyl-phenyl)-pyridin-2-yl]-benzenesulfonamide;
3-Chloro-N-[5-(4-fluoro-2-methyl-phenyl)-pyridin-2-yl]-benzenesulfonamide;
2,4-Dichloro-N-[5-(4-fluoro-2-methyl-phenyl)-pyridin-2-yl]-6-methyl-
benzenesulfonamide;
3-Chloro-N-[5-(2,5-dichloro-phenyl)-6-methyl-pyridin-2-yl]-benzenesulfonamide;
N-[5-(2,5-Dichloro-phenyl)-6-methyl-pyridin-2-yl]-4-fluoro-benzenesulfonamide;
N-[5-(5-Fluoro-2-methyl-phenyl)-6-methyl-pyridin-2-yl]-3-trifluoromethyl-
benzenesulfonamide;
4-Fluoro-N-[5-(5-fluoro-2-methyl-phenyl)-6-methyl-pyridin-2-yl]-
benzenesulfonamide;
3-Chloro-N-[5-(5-fluoro-2-methyl-phenyl)-6-methyl-pyridin-2-yl]-
benzenesulfonamide;
N-[5-(2,5-Dichloro-phenyl)-6-methyl-pyridin-2-yl]-3-trifluoromethyl-
benzenesulfonamide;
N-[5-(2-Chloro-4-fluoro-phenyl)-6-methyl-pyridin-2-yl]-3-trifluoromethyl-
benzenesulfonamide;
N-[5-(2-Chloro-4-fluoro-phenyl)-6-methyl-pyridin-2-yl]-4-fluoro-benzenesulfonamide;
3-Chloro-N-[5-(2-chloro-4-fluoro-phenyl)-6-methyl-pyridin-2-yl]-benzenesulfonamide;
N-[5-(2,3-Dichloro-phenyl)-6-methyl-pyridin-2-yl]-3-trifluoromethyl-
benzenesulfonamide;
N-[5-(2,3-Dichloro-phenyl)-6-methyl-pyridin-2-yl]-4-fluoro-benzenesulfonamide;
3-Chloro-N-[5-(2,3-dichloro-phenyl)-6-methyl-pyridin-2-yl]-benzenesulfonamide;
2,4-Dichloro-N-[5-(2,3-dichloro-phenyl)-6-methyl-pyridin-2-yl]-6-methyl-
benzenesulfonamide;
N-[5-(2,3-Dichloro-phenyl)-6-methyl-pyridin-2-yl]-3-methyl-benzenesulfonamide;
2,4-Dichloro-N-[5-(2,5-dichloro-phenyl)-6-methyl-pyridin-2-yl]-6-methyl-
benzenesulfonamide;
N-[5-(2-Chloro-4-fluoro-phenyl)-6-methyl-pyridin-2-yl]-3-methyl-
benzenesulfonamide;
2,4-Dichloro-N-[5-(2-chloro-4-fluoro-phenyl)-6-methyl-pyridin-2-yl]-6-methyl-
benzenesulfonamide;
N-[5-(2,4-Bis-trifluoromethyl-phenyl)-pyridin-2-yl]-3-chloro-benzenesulfonamide;
N-[5-(2,4-Bis-trifluoromethyl-phenyl)-pyridin-2-yl]-3-methyl-benzenesulfonamide;
N-[5-(2,4-Bis-trifluoromethyl-phenyl)-pyridin-2-yl]-4-fluoro-benzenesulfonamide;
N-[5-(2,3-Dichloro-phenyl)-6-methyl-pyridin-2-yl]-4-fluoro-3-trifluoromethyl-
benzenesulfonamide;
3-Chloro-N-[5-(2,3-dichloro-phenyl)-6-methyl-pyridin-2-yl]-4-fluoro-
benzenesulfonamide;
3-Chloro-N-[5-(2-fluoro-phenyl)-6-methyl-pyridin-2-yl]-benzenesulfonamide;
4-Fluoro-N-[5-(2-fluoro-phenyl)-6-methyl-pyridin-2-yl]-benzenesulfonamide;
4-Fluoro-N-[5-(2-fluoro-phenyl)-6-methyl-pyridin-2-yl]-3-trifluoromethyl-
benzenesulfonamide;
N-[5-(2,4-Bis-trifluoromethyl-phenyl)-pyridin-2-yl]-3-chloro-4-fluoro-
benzenesulfonamide;
2,4-Dichloro-N-[5-(2-fluoro-phenyl)-6-methyl-pyridin-2-yl]-6-methyl-
benzenesulfonamide;
N-[5-(2-Fluoro-phenyl)-6-methyl-pyridin-2-yl]-3-trifluoromethyl-benzenesulfonamide;
N-[5-(2-Chloro-phenyl)-3,4-dimethyl-pyridin-2-yl]-3-trifluoromethyl-
benzenesulfonamide;
3-Chloro-N-[5-(2-chloro-phenyl)-3,4-dimethyl-pyridin-2-yl]-benzenesulfonamide;
N-[5-(2-Chloro-phenyl)-3,4-dimethyl-pyridin-2-yl]-4-fluoro-benzenesulfonamide;
N-(2-Methyl-[3,3']bipyridinyl-6-yl)-3-trifluoromethyl-ben2enesulfonamide;
3-Chloro-N-[5-(2-chloro-phenyl)-4-methyl-pyridin-2-yl]-benzenesulfonamide;
N-[5-(2-Chloro-phenyl)-4-methyl-pyridin-2-yl]-3-trifluoromethyl-benzenesulfonamide;
2,4-Dichloro-N-[5-(2-chloro-phenyl)-4-methyl-pyridin-2-yl]-6-methyl-
benzenesulfonamide;
3-Chloro-N-(2-methyl-[3,3']bipyridinyl-6-yl)-benzenesulfonamide;
3-Chloro-N-[5-(4-fluoro-2-methyl-phenyl)-4-methyl-pyridin-2-yl]-
benzenesulfonamide;
N-[5-(4-Fluoro-2-methyl-phenyl)-4-methyl-pyridin-2-yl]-3-trifluoromethyl-
benzenesulfonamide; and 2,4-Dichloro-N-[5-(4-fluoro-2-methyl-phenyl)-4-methyl-
pyridin-2-yl]-6-methyl-benzenesulfonamide.
17. The compounds as claimed in any one of claims 1 to 16 selected from
N-[5-(2-Chloro-phenyl)-pyridin-2-yl]-5-fiuoro-2-methyl-benzenesulfonamide;
3-Chloro-N-[5-(2-chloro-phenyl)-pyridin-2-yl]-2-methyl-benzenesulfonamide;
3-Chloro-N-[5-(2,4-dichloro-phenyl)-pyridin-2-yl]-2-methyl-benzenesulfonamide;
3-Chloro-N-[5-(2-chloro-phenyl)-6-methyl-pyridin-2-yl]-2-methyl-
benzenesulfonamide;
4,5-Dichloro-N-[5-(2-chlorophenyl)-pyridin-2-yl]-2-fluoro-benzenesulfonamide;
3-Chloro-N-[5-(2,4-dichloro-phenyl)-pyridin-2-yl]-4-methyl-benzenesulfonamide;
Piperidine-1-sulfonic acid [5-(2,4-dichloro-phenyl)-pyridin-2-yl]-amide;
N-[5-(2,3-Dichloro-phenyl)-pyridin-2-yl]-4-fiuoro-benzenesulfonamide;
3-Chloro-N-[5-(2-chloro-phenyl)-6-methyl-pyridin-2-yl]-4-methyl-
benzenesulfonamide;
4-Chloro-N-[5-(2-chloro-phenyl)-6-methyl-pyridin-2-yl]-benzenesulfonamide;
2,4-Dichloro-N-[5-(2-chloro-phenyl)-6-methyl-pyridin-2-yl]-6-methyl-
benzenesulfonamide;
N-[5-(2,4-Dichloro-phenyl)-pyridin-2-yl]-4-fluoro-benzenesulfonamide;
N-[5-(2,4-Dichloro-phenyl)-pyridin-2-yl]-2,4-difluoro-benzenesulfonamide;
3-Chloro-N-[5-(4-fluoro-2-methyl-phenyl)-6-methyl-pyridin-2-yl]-2-methyl-
benzenesulfonamide;
3-Chloro-N-[5-(2,3-dichloro-phenyl)-pyridin-2-yl]-4-methyl-benzenesulfonamide;
3-Chloro-N-[5-(4-fluoro-2-methyl-phenyl)-pyridin-2-yl]-4-methyl-
benzenesulfonamide;
N-[5-(4-Fluoro-2-methyl-phenyl)-pyridin-2-yl]-3-trifluoromethyl-benzenesulfonamide;
N-[5-(2,4-Dichloro-phenyl)-pyridin-2-yl]-3-trifluoromethyl-benzenesulfonamide;
N-[5-(2-Chloro-phenyl)-6-methyl-pyridin-2-yl]-3-trifluoromethyl-benzenesulfonamide;
N-[5-(2-Chloro-phenyl)-pyridin-2-yl]-4-fluoro-benzenesulfonamide;
N-[5-(2-Chloro-phenyl)-6-methyl-pyidin-2-yl]-2,4-difluoro-benzenesulfonamide;
N-[5-(2,4-Dichloro-phenyl)-6-methyl-pyridin-2-yl]-2,4-difluoro-benzenesulfonamide;
2,4-Dichloro-N-[5-(2,4-dichloro-phenyl)-pyridin-2-yl]-6-methyl-benzenesulfonamide;
2,4-Dichloro-N-[5-(2-chloro-phenyl)-6-methyl-pyridin-2-yl]-benzenesulfonamide;
N-[5-(4-Fluoro-2-methyl-phenyl)-6-methyl-pyridin-2-yl]-3-trifluoromethyl-
benzenesulfonamide;
3-Chloro-N-[5-(4-fluoro-2-methyl-phenyl)-6-methyl-pyridin-2-yl]-
benzenesulfonamide;
N-[5-(4-Fluoro-2-methyl-phenyl)-6-methyl-pyridin-2-yl]-3-methyl-
benzenesulfonamide;
N-[5-(5-Fluoro-2-methyl-phenyl)-pyridin-2-yl]-3-trifluoromethyl-benzenesulfonamide;
N-[5-(5-Chloro-2-methyl-phenyl)-pyridin-2-yl]-3-trifluoromethyl-benzenesulfonamide;
N-[5-(6-Chloro-2-fluoro-3-methyl-phenyl)-pyridin-2-yl]-4-fluoro-benzenesulfonamide;
3-Chloro-N-[5-(4-fluoro-2-methyl-phenyl)-pyridin-2-yl]-benzenesulfonamide;
2,4-Dichloro-N-[5-(4-fluoro-2-methyl-phenyl)-pyridin-2-yl]-6-methyl-
benzenesulfonamide;
4-Fluoro-N-[5-(5-fluoro-2-methyl-phenyl)-6-methyl-pyridin-2-yl]-
benzenesulfonamide;
N-[5-(2-Chloro-4-fluoro-phenyl)-6-methyl-pyridin-2-yl]-3-trifluoromethyl-
benzenesulfonamide;
2,4-Dichloro-N-[5-(2,3-dichloro-phenyl)-6-methyl-pyridin-2-yl]-6-methyl-
benzenesulfonamide;
2,4-Dichloro-N-[5-(2-chloro-4-fluoro-phenyl)-6-methyl-pyridin-2-yl]-6-methyl-
benzenesulfonamide;
N-[5-(2,4-Bis-trifluoromethyl-phenyl)-pyridin-2-yl]-3-chloro-benzenesulfonamide;
3-Chloro-N-[5-(2-chloro-phenyl)-4-methyl-pyridin-2-yl]-benzenesulfonamide;
N-[5-(2-Chloro-phenyl)-4-methyl-pyridin-2-yl]-3-trifluoromethyl-benzenesulfonamide;
3-Chloro-N-[5-(4-fluoro-2-methyl-phenyl)-4-methyl-pyridin-2-yl]-
benzenesulfonamide;
N-[5-(4-Fluoro-2-methyl-phenyl)-4-methyl-pyridin-2-yl]-3-trifluoromethyl-
benzenesulfonamide; and
2,4-Dichloro-N-[5-(4-fluoro-2-methyl-phenyl)-4-methyl-pyridin-2-yl]-6-methyl-
benzenesulfonamide.
18. A process for the preparation of a compound as claimed in any one of claims 1 to 17
comprising the reaction of a compound according to formula
(Formula Removed)
in the presence of a compound according to formula
(Formula Removed)
wherein R1 to R7, A, E and G are defined as in claim 1.
19. The compounds as claimed in any one of claims 1 to 17 for use as therapeutically active
substance for the preparation of medicaments for the prophylaxis and therapy of
illnesses which are caused by disorders associated with the enzyme 11beta-
hydroxysteroid dehydrogenase 1 such as diabetes including diabetes Type II, obesity,
eating disorders, dyslipidemiae and hypertension.
20. A pharmaceutical composition as and when prepared using a compound as claimed in any one of claims 1 to 17 and a therapeutically inert carrier.
21. The compounds as claimed in any one of claims 1 to 17, when manufactured according to a process of claim 18.

Documents:

778-DELNP-2007-Abstract-(17-01-2012).pdf

778-DELNP-2007-Abstract-(29-03-2012).pdf

778-delnp-2007-abstract.pdf

778-delnp-2007-assignments.pdf

778-delnp-2007-Claims-(17-01-2012).pdf

778-delnp-2007-claims-(29-03-2012).pdf

778-delnp-2007-claims.pdf

778-DELNP-2007-Correspondence Others-(17-01-2012).pdf

778-DELNP-2007-Correspondence Others-(29-03-2012).pdf

778-delnp-2007-correspondence-others-1.pdf

778-DELNP-2007-Correspondence-Others.pdf

778-DELNP-2007-Description (Complete)-(17-01-2012).pdf

778-DELNP-2007-Description (Complete)-(29-03-2012).pdf

778-delnp-2007-description (complete).pdf

778-delnp-2007-form-1.pdf

778-delnp-2007-form-18.pdf

778-DELNP-2007-Form-2-(17-01-2012).pdf

778-DELNP-2007-Form-2-(29-03-2012).pdf

778-delnp-2007-form-2.pdf

778-DELNP-2007-Form-3-(17-01-2012).pdf

778-delnp-2007-form-5.pdf

778-DELNP-2007-GPA-(17-01-2012).pdf

778-delnp-2007-gpa.pdf

778-delnp-2007-pct-210.pdf

778-delnp-2007-pct-304.pdf

778-delnp-2007-pct-409.pdf

779-DELNP-2007-Form-3.pdf

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Patent Number 252825
Indian Patent Application Number 778/DELNP/2007
PG Journal Number 23/2012
Publication Date 08-Jun-2012
Grant Date 01-Jun-2012
Date of Filing 31-Jan-2007
Name of Patentee F. HOFFMANN-LA ROCHE AG
Applicant Address GRENZACHERSTRASSE 124 CH-4070 BASEL (SWITZERLAND)
Inventors:
# Inventor's Name Inventor's Address
1 AMREIN, KURT LETTENWEG 8, CH-4452, SWITZERLAND
2 HUNZIKER, DANIEL BUERKLISTRASSE 14, CH-4313 MOEHLIN,SWITZERLAND
3 KUHN, BERND SONNMATTWEG 42, CH-4410 LIESTAL, SWITZERLAND
4 MAYWEG, ALEXANDER MARTINSASSE 8, CH-4051 BASEL, SWITZERLAND
5 NEIDHART, WERNER 9, RUE DU STEINLER, F-68220 HAGENTHAL-LE-BAS, FRANCE
PCT International Classification Number A61K 31/435
PCT International Application Number PCT/EP2005/007894
PCT International Filing date 2005-07-20
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 04103639.3 2004-07-28 EUROPEAN UNION