Title of Invention

PROCESS FOR PREPARING SUBSTITUTED BENZOPYRAN COMPOUNDS

Abstract A process of preparing benzopyran compounds of formula 1, its intermediates, its salts or its solvates, wherein the compound of formula 2 is reacted with compound of formula 3, using an organic solvent in the presence of a Pd or Cu catalyst, diamines or phosphamines as ligand and a base.
Full Text Field of Invention
The present invention relates to a novel method of preparing substituted benzopyran compounds of the following formula 1, their corresponding novel intermediates and a method of their preparation thereof.
(Formula Removed)In the above formula 1, R1, R2, R3, R4, A and Yare the same as defined in the detailed description of the invention.
Background of Invention
A benzopyran compound is a leukotriene-receptor antagonist already disclosed in EP 0173516 and others, which is also known as a therapeutic agent for treating diseases induced by leukotriene and 5-a-reductase. For example, JP Hei 3-95144 discloses a method of preparing 3-amino-2-hydroxyacetophenone from the phenol compound of the following formula (A) via a four step process. However, this method is not considered efficient due to its rather long process and also it lacks industrial applicability due to the risk of explosion during a hydrogenation reaction using Pd/C in the reduction step (a) for introducing an amino group.
(Formula Removed)
In the above reaction, X indicates a halogen atom.
Meanwhile, in USP 5,675,036, and 5,597,929 and W094/124923, their methods of synthesis are not suitable in terms of safety and environmental aspects because not only they employ an acetophenone compound (D) as an intermediate which is rather difficult to be synthesized, but also they use highly explosive and corrosive reagent, SOC12, for prepariing acyl chloride (E) required for introducing an amide group from amine moiety. Further, the acyl chloride thus produced is in general not very stable and is very difficult to adjust during the commercial

(Formula Removed)



This invention relates to a method of synthesizing a few novel benzopyran compounds disclosed in EP 0173516. The method of the present invention is industrially more applicable since it provides an added safety and efficiency with a fewer number of steps in process as compared to the conventional methods. In particular, the method of this invention follows the convergent pathway, a more
efficient process than the conventional linear process. Further, the method of the present invention does not employ a risky process such as hydrogenation reaction and the intermediate materials produced during the reaction are so stable that their separation and purification are quite easy.

STATEMENT OF THE INVENTION.
A process of preparing benzopyran compounds of formula 1,
(Formula Removed)



its intermediates, its salts or its solvates, wherein the compound of formula 2 is reacted with compound of formula 3, using an organic solvent in the presence of a Pd or Cu catalyst, diamines or phosphamines as ligand and a base.
Detailed Description of Invention
This invention relates to a method of preparing substituted benzopyran compounds having the chemical structure of the following formula 1, a novel intermediate compound used for the process thereof, and a method of preparing the intermediate compound.
(Formula Removed)

In the above formula 1,
R1 is selected from the group consisting of a C1-20 alkyl group, a C2-20 alkenyl group, a C2-20 alkynyl group, a phenyl group, a naphthalenyl group and an indanyl group, wherein the groups can be independently substituted by 1 or 2 substituents selected from a C1-20 alkyl group, a C2-20 alkenyl group and a C2-20 alkynyl group, wherein up to 5 carbon atoms of the substitution groups can be selectively substituted by O, S, N, a halogen atom, a benzene ring, a thiophene ring, a naphthalene ring, a C4-7 carbocyclic ring, a carbonyl group, a carbonyloxy group, a hydroxyl group, a carboxy group, an azido group or a nitro group;

R2 and R4 are independently H, a C1-6 alkyl group, a C2-6 alkenyl group, a alkyl group substituted with from 1 to 3 aryl groups, a C1-6 alkoxycarbonyl group, a C1-6 alkoxycarbonyl group substituted with an aryl group, an aryloxycarbonyl group, a C1-6 alkoxy C1-6 alkyl group, a C3-9 trialkyltin group, a triaryltin group, or a C3-9 trialkylsylyl group, wherein the aryl group or said aryl is a phenyl group substituted with from 1 to 3 substituents which are selected from the group consisting of a phenyl group, a halogen atom, a C1-6 alkyl group and a C1-6 alkoxy group;
R3 is H, a halogen atom, a hydroxy group, a nitro group, a C1-6 alkyl group, a C1-6 alkoxy group, a C1-6 alkylthio group, or -COOR5 (wherein R5 is H or a C1-6 alkyl group);
A is a single bond; or a C1-10 alkylene group, a C2-10 alkenylene group, or a C2-10 alkynylene group either substituted or unsubstituted with from 1 to 3 substituents selected from a C1-10 alkyl group and a phenyl group;
X is a halogen atom; and
Y is O or S.
In preparing the substituted benzopyran compounds of the above formula 1, R1 is a phenyl group or a substituted phenyl group, wherein the above substituted phenyl group can be substituted with 1 or 2 substituents selected from a C1-20 alkyl group, a C2-20 alkenyl group and a C2-20 alkynyl group, wherein up to 5 carbon atoms of the substitution groups can be selectively substituted by O, S, N, a halogen atom, a benzene ring, a thiophene ring, a naphthalene ring, a C4-7 carbocyclic ring, a carbonyl group, a carbonyloxy group, a hydroxyl group, a carboxy group, an azido
group or a nitro group. Preferably, R1 is a phenyl group substituted at p-position with a substituent from those exemplified above, and more preferably
(Formula Removed)
In preparing the substituted benzopyran compounds of the above formula 1, R2 and R4 are independently H, a C1-6 alkyl group, a C1-6 alkenyl group, a C1-6 alkyl group substituted with from 1 to 3 aryl groups, or a C1-6 alkoxycarbonyl group. More preferably, R2 and R4 are independently H.
In preparing the substituted benzopyran compounds of the above formula 1, R3 is H.
In preparing the substituted benzopyran compounds of the above formula 1, A is a single bond; or a methylene, ethylene, trimethylene, tetramethylene, vinylene, propenylene, butenylene, butadienylene or ethynylene group either substituted or unsubstituted with from 1 to 3 substituents selected from a C1-10 alkyl group and a phenyl group. More preferably, A is a single bond.
The substituted benzopyran compounds of the above formula 1 according to the present invention can be prepared by reacting a compound of the following formula 2 with a compound of the following formula 3 as shown in the following reaction scheme 1.
[Reaction Scheme 1]
(Formula Removed)
In the above reaction scheme 1, R1, R2, R3, R4, A, X and Y are the same as defined in the above formula 1.
The above preparation method according to the reaction scheme 1 is performed at reflux temperature using an organic solvent in the presence of a Pd or Cu catalyst, a ligand and a base.
The solvent used in the above reaction can be selected from those having high polarity such as N,N'-dimethylformamide, N-methylpyrolidone, pyridine, 1,4-dioxane, C1-6 alkanol(methanol, ethanol, t-butanol) or a mixture thereof, and preferably N,N'-dimethylformamide.
The catalyst used in the above reaction is a Pd- or Cu-containing compound and is used in the range of about 0.1 to 100 mol% with reference to the amount of reactants. Preferably, the catalyst is selected from the group consisting of Cul, CuCl, and Qu2O, and more preferably Cul.
The ligand in the above reaction is used in the range of about 0.5 to 3
equivalents with reference to the amount of the catalyst being used. The ligand used
is diamines or phosphines, preferably the one selected from the group consisting of
N,N'-dimethylethylenediamine, trans-N,Nl-l,2-cyclohexanediamine and trans-.N,N1-
dimethyl-l,2-cyclohexanediamine, and more preferably N,N
dimethylethylenediamine.
The base in the above reaction is used in the range of about 1 to 10 equivalents with reference to the substrate material. The base can be selected from the group consisting of alkali metal alkoxide such as potassium t-butoxide, potassium methoxide, and sodium methoxide; hydrides such as sodium hydride and potassium hydride; alkali metal carbonate such as potassium carbonate, cesium carbonate, and sodium carbonate; or an alkali metal phosphate such as potassium phosphate and sodium phosphate; and preferably an alkali metal phosphate.
In a preferred embodiment of the preparation method according to the reaction scheme 1, as shown in the following reaction scheme la, the substituted benzopyran compounds of the following formula la, its salts or its solvates (e.g., hydrates) are synthesized by reacting a compound of the following formula 2a with a compound of the following formula 3a, its salts or its solvates (e.g., hydrates).
[Reaction Scheme la]
(Formula Removed)
In the above reaction scheme la, the reaction is performed while stirring at about 70 to about 100°C for more than a day using N,N'-dimethylformamide as a solvent in the presence of Cul as a catalyst, N,N'-dimethylethylenediainine as a ligand, and potassium phosphate as a base.
Meanwhile, in performing the synthesis according to the above reaction scheme 1, the reactants, i.e., the compound of the above formula 2 (especially the
compound of the above formula 2a) and the compound of the above formula 3 (especially the compound of the above formula 3a), are novel intermediate compounds used in synthesizing the compound of the above formula 1. Therefore, the compounds of the above formulas 2 and 3 also belong to the scope of the present invention.
The compound of the above, formula 2, being a novel intermediate compound according to the present invention, can be synthesized by hydrolysis of the compound of the following formula 4 as shown in the following reaction scheme 2. [Reaction Scheme 2]
(Formula Removed)
In the above reaction scheme 2, R1, R2, A and Y are the same as defined in the
above formula 1.
In the above reaction scheme 2, an amide group is introduced via hydrolysis using a base in the presence of water, an organic solvent or their mixture. The conditions for a base/solvent used in the above hydrolysis will be apparent to those skilled in the art. For example, the reaction is performed using a single C1-6alkanol solvent such as methanol, ethanol, f-butanol or their mixture as a solvent while using alkali hydroxide such as sodium hydroxide or potassium hydroxide as a base.
In a preferred embodiment of the preparation method via the hydrolysis according to the reaction scheme 2, as shown in the following reaction scheme 2a, the compounds of the following formula 2a, its salts or its solvates (e. g., hydrates)
are synthesized by reacting the compound of the following formula 4a in the presence of NaOH/f-butanol. [Reaction Scheme 2a]

(Formula Removed)
Further, the compound of the following formula 3, being a novel intermediate compound of the present invention, can be prepared by (a) synthesizing the compound of the following formula 7 by reacting the compound of the following formula 5 with the compound of the following formula 6, and then (b) performing cyclization reaction of thus obtained compound of the following formula 7, as shown in the following reaction scheme 3.
[Reaction Scheme 3]
(Formula Removed)
In the above reaction scheme 3, R3, R4 and X are the same as defined in the above formula 1 and Z indicates an activated leaving group.
Examples of the activated leaving group (Z) of the above reaction scheme 3 are, for example, a halogen atom, an activated amide group represented by -N(R6)(OR6) (wherein R6is a C1-6 alkyl group), R7O-, R7S- or R7SO2O- (wherein R7is a C1-6 alkyl group, an arbitrarily substituted phenyl group or an arbitrarily substituted phenyl C1-6 alkyl group), or
(Formula Removed)
(wherein R8 is a C1-6 alkyl group, an arbitrarily substituted phenyl group or an arbitrarily substituted phenyl C1-6 alkyl group, Y's are independently O or S). .
Preferably, the activated leaving group is R7O-,
wherein R7 is a C1-6 alkyl group, an arbitrarily substituted phenyl group or an arbitrarily substituted phenyl C1-6 alkyl group, more preferably, R7 is a C1-6 alkyl group, for example, a methyl group, an ethyl group, i—butyl group or t-butyl group, and most preferably R7is an ethyl group.
The step (a) of the synthesis according to the above reaction scheme 3 is performed in the presence of N,N'-dimethylformamide, an ether solvent such as tetrahydrofuran; an organic solvent such as toluene, benzene, hexane or a C1-6 alkanol (e.g., methanol, ethanol, f-butanol); and a base, wherein the base can be selected from the group consisting of alkali metal alkoxide such as potassium t-butoxide, potassium methoxide, and sodium methoxide; hydrides such as sodium hydride; and amides such as potassium amide and sodium amide.
The cyclization in step (b) of the synthesis according to the above reaction scheme 3 is performed in the presence of an acid. For example, the cyclization can be performed in the presence of a sulfuric acid using a solvent such as C1-6 alkanol or acetic acid. Further, the cyclization can be performed in the presence of hydrochloric acid in the mixed solvent of C1-6 alkanol/tetrahydrofuran.
Alternative acid/sol vent conditions will be apparent to those skilled in the art. The reaction can be performed in a suitable solvent such as water or C1-6 alkanol, unsaturated carbocyclic hydrocarbon such as benzene or toluene, by using an acid
such as hydrobromic acid, hydroiodic acid, perchloric acid or p-toluenesulfonic acid; and a Lewis acid such as aluminum trichloride or titanium, tetrachloride. Preferably, the above reaction is performed in methanol solvent in the presence of sulfuric acid. In a preferred embodiment of the preparation method according to the reaction scheme 3, as shown in the following reaction scheme 3a, the compounds of the following formula 3a, its salts or its solvates (e.g., hydrides) are prepared by (a) synthesizing the compound of the following formula 7a, its salts and its solvates (e.g., hydrides) by reacting the compound of the following formula 5a with the compound of the following formula 6a, its salts and its solvates (e.g., hydrides) and then (b) performing the cyclization reaction of the compound of the following formula 7a, its salts and its solvates.
[Reaction Scheme 3a]
(Formula Removed)
Meanwhile, in performing the synthesis according to the above reaction scheme 3, the compound of the above formula 7 (especially the compound of the above formula 7a) is a novel intermediate compound synthesized during the reaction. Therefore, the compound of the above formula 7 also belongs to the scope of the present invention.
The compound of the above formula 7 is indicated as di-keto type in this invention for convenience, but it can be also present in the form of keto-enol and
cyclic hydroxy chromanone. Therefore, all of the tautomeric forms of the above formula 7 belong to the scope of this invention.
Cyclic hydroxy chromanone
(Formula Removed)
Examples
A better understanding of the present invention may be obtained in light of the
following examples which are set forth to illustrate, but are not to be construed to limit the present invention.
Example 1: Preparation of 4- (4-phenylbutoxy)benzamide
To a mixture of 4-(4-phenylbutoxy)benzonitrile (1.9 g, 7.5 mmol) and t-butanol (37 mL) was added NaOH (2.1 g, 38 mmol) and refluxed for 4 hours. The mixture was cooled to room temperature and then added to a mixed solution of water and methanol (4 : 1,100 mL). The resulting precipitate was filtered, washed with water and then dried under vacuum to give the target compound as a white solid (1.9 g, 94%).
1H NMR(300MHz, DMSO-d6) 6 7.81-7.83(m, 3H), 7.15-7.30(m, 6H), 6.95(d, /=9.0Hz, 2H), 4.04(t, /=5.9Hz, 2H), 2.65(t, J=6.9Hz, 2H), 1.73(1, J=3.2Hz, 4H)
Example 2: Preparation of 2-iodo-6-[l,3-dioxo-3-(tetrazol-5-yl)propyl]phenol
Under the nitrogen atmosphere, anhydrous dimethylf ormamide (30 mL) was added to a mixture of 2-hydroxy-3-iodoacetophenone (1.5 g, 5.7 mmol), ethyl-lH-tetrazol-5-carboxylate (1.1 g, 7.5 mmol) and potassium t-butoxide (32 g, 28.7 mmol) and then stirred at 50 °C for 3 hours. The mixture was cooled to room temperature and then slowly added to cold IN HQ (120 mL). The resulting orange precipitate was filtered, washed with water and then dried under vacuum to obtain the target compound. The target compound was dissolved in ethylacetate by applying heat, added with hexane and then placed at 0 °C for 2 hours. The resulting product was filtered, washed with hexane and then dried under vacuum to give the purified product as a yellow solid (1.7 g, 83%).
1H NMR(300MHz, DMSO-de) 8 8.99(br s, 1H), 8.10(dd, J=7.7, l.SHz, 1H), 7.80(dd, 7=8.0, l.THz, 1H), 6.95(t, J=7.8Hz, 1H), 3.57(d, J=16.5Hz, 1H), 3.20(d, J=16.5Hz, 1H)
Example 3: Preparation of 8-iodo-4-oxo-2-tetrazol-5-yl-lH-l-benzopyran
The purified product obtained in Example 2(1.5 g, 4.2 mmol) was mixed in methanol(20 mL) and stirred to produce a slurry. The slurry was then added with a cone, sulfuric acid (265 µL, 5.0 mmol) and refluxed for 7 hours. The mixture was cooled to room temperature and then maintained at 0 °C for an hour. The resulting product was filtered, washed with cold methanol, water and cold methanol. The resulting product was dried under vacuum to afford the target compound as a pale yellow solid(1.3g, 93%).
1H NMR(300MHz, DMSO-&) 68.35(dd, J=7.7, l.THz, 1H), 8.07(dd 7=7.8, l.SHz, 1H), 7.33(1, J=8.0,1H), 7.11(8,1H)
Example 4: Preparation of 4-oxo-8-[4-(4-phenylbutoxy)benzoylainino]-2-tetrazoI-5-yl-4H-l-benzopyran
Under the nitrogen atmosphere, the purified product obtained in Example 1 (108 mg, 0.40 mmol), the purified product obtained in Example 3 (68 mg, 0.20 mmol), Cul (11.4 mg, 0.04 mmol), potassium phosphate (255 mg, 0.80 mmol) and N,N'-dimethylethylenediamine (13 µL, 0.08 mmol) were mixed together. The mixture was then added with anhydrous dimethylfonnamide (1 mL) and stirred at 100 °C for two days. The reaction solution was cooled to room temperature and added with water(15 mL). The resulting solution was acidified to pHl-2 by adding a saturated HC1 solution. The precipitated solid was filtered and the resulting solid was suspended in methanol(10mL) and then filtered to remove the remaining purified product obtained in Example 1. The obtained solid was dissolved in methanol(7mL) by adding sodium acetate (32 mg, 0.40 mmol) and then filtered. The filtrate was added with saturated HC1 solution. The precipitated solid was filtered, washed with cold methanol and then dried under vacuum to obtain the target compound as a pale yellow solid(77 mg, 81%).
Industrial Applicability
As stated above, the present invention relates to a manufacturing process suitable for industrial application, which provides a much improved and more efficient method with secured safety as compared to the conventional methods. In
particular, the compounds represented in the above formulas 2, 3 and 7 are novel intermediate compounds produced in the course of synthesizing substituted benzopyran compounds of the formula 1, and they will also be very useful in industrial application due to their great stability.
The invention has been described in detail with reference to preferred embodiments thereof. However, it will be appreciated that those skilled in the art, upon consideration of the disclosure, may make modifications and improvements within the scope and spirit of the invention.






We Claim:

1. A process of preparing benzopyran compounds of formula 1,
(Formula Removed)
wherein R1 is selected from the group consisting of a C1-20 alkyl group, a C2-20 alkenyl group, a C2-20 alkynyl group, a phenyl group, a naphthyl group and an indanyl group, wherein said groups can be independently substituted by 1 or 2 substituents selected from a C1-20 alkyl group, a C2-20 alkenyl group and a C2-20 alkynyl group, wherein up to 5 carbon atoms of said substitution groups can be optionally substituted by O, S, N, a halogen atom, a benzene ring, a thiophene ring, a naphthalene ring, a C4-7 carbocyclic ring, a carbonyl group, a carbonyloxy group, a hydroxy group, a carboxy group, an azido group or a nitro group; R2 and R4 are independently H, a C1-6 alkyl group, a C2-6 alkenyl group, a C1-6 alkyl group substituted with from 1 to 3 aryl groups, a C1-6 alkoxycarbonyl group, a C1-6 alkoxycarbonyl group substituted with an aryl group, an aryloxycarbonyl group, a C1-6 alkoxyC1-6 alkyl group, a C3-9 trialkyltin group, a triaryltin group, or a C3-9 trialkylsilyl group, wherein said aryl group or said aryl is a phenyl group substituted with from 1 to 3 substituents which are selected from the group consisting of a phenyl group, a halogen atom, a C1-6 alkyl group and a C1-6 alkoxy group;

R3 is H, a halogen atom, a hydroxy group, a nitro group, a C1-6 alkyl group, a C1-6
alkoxy group, a C1-6 alkylthio group, or -COOR5 (wherein R5 is H or a C1-6 alkyl
group);
A is a single bond; or a C1-10 alkylene group, a C2-10 alkenylene group, or a C2-10
alkynylene group either substituted or unsubstituted with from 1 to 3 substituents
selected from a C1-10 alkyl group and a phenyl group;
X is a halogen atom; and
Y is O or S,
its intermediates, its salts or its solvates, wherein the compound of formula 2 is
reacted with compound of formula 3, using an organic solvent in the presence of a
Pd or Cu catalyst, diamines or phosphamines as ligand and a base.
2. The compound of the process as claimed in claim 1, wherein R1 is,
(Formula Removed)

R2, R3 and R4 are independently H, A is a single bond, X is I, Br or C1; Y is O.
3. The process as claimed in claim 1, wherein the solvent is selected from the group consisting of N,N'-dimethylformamide, N-methylpyrolidone, pyridine, 1,4 dioxane, C1-6 alkanol (methanol, ethanol, t-butanol) or a mixture thereof.
4. The process as claimed in claim 3, wherein the solvent is preferably N,N'-dimethylformamide.

5. The process as claimed in claim 1, wherein the catalyst is selected from the group consisting of CuL, CuCl, and CU2O.
6. The process as claimed in claim 5, wherein the catalyst is preferably CuI
7. The process as claimed in claim 1, wherein the ligand is selected from the group consisting of N,N'-dimethylethylenediamine, trans-N,N'-l,2-cyclohexanediamine and trans-N,N' -dimethyl-1,2-cyclohexanediamine.
8. The process as claimed in claim 7, wherein the ligand is preferably N,N'-dimethylethylenediam ine.
9. The process as claimed in claim 1, wherein the base is selected from the group consisting of alkali metal alkoxide such as sodium hydride and potassium hydride; alkali metal carbonate such as potassium carbonate, cesium carbonate and sodium carbonate or an alkali metal phosphate such as potassium phosphate and sodium phosphate.
10. The process as claimed in claim 9, wherein the base is preferably potassium phosphate.
11. The process a claimed in claim 1, wherein the compound 2 is of formula 2a is reacted with the compound 3 of formula 3 a to obtain a compound of formula la,
(Formula Removed)



its salts and its solvates.
12. The process as claimed in claim 1, wherein the preparation of compound of formula 3 comprises the step of:
(a) Reacting a compound of formula 5 and a compound of formula 6 to obtain a compound of formula 7, its salts and solvates; and
(b) performing a cyclization of the compound obtained in (a),

(5)

wherein R , R and X are as defined in claim 1, and Z indicates an activated leaving
(Formula Removed)

group.
13. The process as claimed in claim 12, wherein said cyclization is performed by using methanol as a solvent in the presence of sulfuric acid.
14. The process as claimed in claim 1 and 12, wherein the preparation of compound 3 is of formula 3a comprises the step of:

(a) preparing a compound of the following formula 7a by reacting a compound of the following formula 5a and a compound of the following formula 6a, its salts or its solvates; and,
(b) performing a cyclization of the compound obtained in (a).

(Formula Removed)


15. A compound and a method of preparing a compound substantially as herein described with reference to the foregoing examples.



Documents:

4970-DELNP-2006-Abstract-(23-07-2009).pdf

4970-DELNP-2006-Abstract.pdf

4970-DELNP-2006-Claims-(23-07-2009).pdf

4970-delnp-2006-claims.pdf

4970-delnp-2006-correscpondence-others-1.pdf

4970-DELNP-2006-Correspondence-Others-(23-07-2009).pdf

4970-delnp-2006-correspondence-others.pdf

4970-DELNP-2006-Description (Complete)-(23-07-2009).pdf

4970-delnp-2006-description (complete).pdf

4970-DELNP-2006-Form-1-(23-07-2009).pdf

4970-delnp-2006-form-1.pdf

4970-delnp-2006-form-18.pdf

4970-DELNP-2006-Form-2-(23-07-2009).pdf

4970-delnp-2006-form-2.pdf

4970-delnp-2006-form-26.pdf

4970-DELNP-2006-Form-3-(23-07-2009).pdf

4970-delnp-2006-form-3.pdf

4970-delnp-2006-form-5.pdf

4970-delnp-2006-pct-237.pdf

4970-delnp-2006-pct-301.pdf

4970-delnp-2006-pct-304.pdf

4970-delnp-2006-pct-308.pdf

4970-delnp-2006-pct-409.pdf

4970-DELNP-2006-Petition-137-(23-07-2009).pdf


Patent Number 241518
Indian Patent Application Number 4970/DELNP/2006
PG Journal Number 29/2010
Publication Date 16-Jul-2010
Grant Date 09-Jul-2010
Date of Filing 29-Aug-2006
Name of Patentee SK CHEMICALS, CO., LTD.
Applicant Address 600 JUNGJA 1-DONG, JANGAN-GU, SUWON-SI, GYEONGGI-DO 440-301, REPUBLIC OF KOREA
Inventors:
# Inventor's Name Inventor's Address
1 LEE, NAM KYU 123-108 JUGONG APT., 333, CHEONCHEON-DONG, JANGAN-GU, SUWON-SI, GYEONGGI-DO 440 330, REPUBLIC OF KOREA
2 LEE, JU YOUNG 105-1502 DONGSIN APT., 401 JUNGJA-DONG, JANGAN-GU, SUWON-SI, GYEONGGI-DO 440 300, REPUBLIC OF KOREA
3 KIM, JAE-SUN 15/5 1146-3, SERYU 2-DONG, GWONSEON-GU, SUWON-SI, GYEONGGI-DO 441-112, REPUBLIC OF KOREA
4 JUNG, JAE YOON 2 CHA 402 WORLD VILLA, 232 NEGAK-LI, JINJEOP EUP, NAMYANGJU-SI, GYEONGGI-DO 472-862, REPUBLIC OF KOREA
5 UM, KEY AN 102-305 HANIL TOWN, JOWON-DONG, JANGAN-GU, SUWON-SI, GYEONGGI-DO 440 290, REPUBLIC OF KOREA
6 OH, YONG HO 103-606 SETBYEOL HANYANG APT., DALAN-DONG, DONGAN-GU, ANYANG-SI, GYEONGGI-DO 431-719, REPUBLIC OF KOREA
7 SHIN, HO CHUL 217-1302 JUGONG NEW TOWN, 861, JOWON-DONG, JANGAN-GU, SUWON-SI, GYEONGGI-DO 440-200, REPUBLIC OF KOREA
8 JANG, WOO JAE 725-28 GEUMJEONG-DONG, GUNPO-SI, GYEONGGI-DO 435-050, REPUBLIC OF KOREA
9 IM, GUANG-JIN 406-1202 HYUNDAI APT., 1343 SA-DONG, ANSAN-SI, GYEONGGI-DO 425-170, REPUBLIC OF KOREA
10 KIM, TAE KON A LABORATORY OF SK CHEMICALS CO., LTD., JUNGJA-DONG, JANGAN-GU, SUWON-SI, GYEONGGI-DO, 440-300, REPUBLIC OF KOREA.
PCT International Classification Number C07D 405/04
PCT International Application Number PCT/KR2005/000365
PCT International Filing date 2005-02-07
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 10-2004-0009280 2004-02-12 Republic of Korea