Title of Invention

"A PROCESS FOR THE PREPARATION OF NOVEL N1, Nn-DIGLYCOSYLATED DIAMINOALCOHOL USEFUL IN CHEMOTHERAPY OF TUBERCULAR INFECTIONS.

Abstract 1. A process for the preparation novel N1,Nn-diglycosylated diaminoalcohols of the general formula 2, wherein RI is selected from 1-4 carbon atom alkyl chain and aralkyl group, X is selected from the group consisting of 1-16 carbon, branched or unbranched alkyl, substituted or unsubstituted alkyl and aryl and substituted or unsubstituted diureidyl aryl, useful as antitubercular agent which comprises reducing glcosyl amino ester of formula 1, wherein R1 is selected from group consisting of 1-4 carbon atom alkyl chain and aralkyl group, R is 1-4 carbon atom alkyl chain , X is selected from the group consisting of 1-16 carbon, branched or unbranched alkyl, substituted or unsubstituted aryl, and substituted or unsubstituted diureidyl aryl with a reducing agent in an organic solvent at a temperature in the range of 0-25 °C in an inert atmosphere, filtering the above said reaction mixture to obtain the solid cake mass followed purification by known methods to obtain the desired product.
Full Text The present invention relates to a process for the preparation of novel N , N -diglycosylated diaminoalcohols useful as antitubercular agents. More particularly the present invention relates to the novel N', N~-diglycosylated diaminoalcohols. These compounds are useful in the chemotherapy of tuberculosis.


Despite the availability of effective and short course chemotherapy and BCG vaccine the tubercular baccilus continues to claim more lives than any other single infectious agent. A number of substances other than the antibiotics have been proposed heretofore for use in treating tubercular and fungal infections, but they have not been used extensively for a number of reasons. Among them the increased incidence of multidrug resistant tuberculosis, its deadly synergy with human immunodeficiency virus and susceptibility to fungal infections in tuberculosis and resistance to existing antifungals are the prominent ones. Many potentially effective antitubercular and antifungal agents are toxic and cannot be safely administered to patients and still some of them have undesirable side effects. As a result of the foregoing and other deficiencies, it is apparent that the development of new class of nontoxic mechanism based broad-spectrum antimicrobial agents has not been available for treating the tubercular and fungal infections.
Ethambutol an amino alcohol is clinically used antitubercular drug but it is associated with many drawbacks and resistant cases against this drug are also appearing. It has been discovered that certain glycosylated amino acids are associated with a number of biological activities as these provide important biological signals to the cells in order to combat the adverse conditions (Varki A., Glycobiology (1993), 3, 97 & Drickamen, K. In molecular glycobiology Flukada, M., Hindsgaul. 0., Eds IRL, Oxford 1994, Ch2, pp53-87). Further sugar derivatives are known to offer better pharmacokinetic parameter to the


(Formula Removed)
drugs and at the same time they are less toxic in comparison to other class of compounds [J.F.Fisher, Harrison, A.W., Bundy G.L., K.F. Willinkson, Rush B.D., Ruwart M.J., J. Med. Chem (1991, 34, 3410 & Negre E., Driaf K.P., Veraneuil B, Tetrahedron Lett ~(1~93), 34, 1027]. Thoxyl, a thiourea derivative, an antitbercular compound is associated many drawbacks. Further, glycoconjugates are known to be superior ligands with higher affinity than a natural carbohydrate ligand [P. M. St. Hilaire and M. Meldal Angew.

Chem. mt. Ed (2000, 39, 1162)].

The main objective of the present invention is to provide novel N , N -

diglycosylated diaminoalcohols useful as antitubercular agents. More particularly the present invention relates to the novel N', N~-diglycosylated diaminoalcohols. These compounds are useful in the treatment of tubercular infections.

Another objective of the present invention is to provide a process for the preparation of novel N', N~-diglycosylated diaminoalcohols of the general formula 2 (Figure- 1).

Yet another objective of the present invention is to provide compounds of formula 2, useful in the treatment of tubercular infections.
Accordingly the present invention provides a process for the preparation novel ',N~diglycosylated diaminoalcohols of the general formula 2,

wherein R, is selected from 1-4 carbon atom alkyl chain and aralkyl group, X is selected from the group consisting of 1-16 carbon, branched or unbranched alkyl, substituted or unsubstituted alkyl and aryl and substituted or unsubstituted diureidyl aryl, useful as antitubercular agent which comprises reducing glcosyl amino ester of formula 1, wherein R1 is selected from group consisting of 1-4 carbon atom alkyl chain and aralkyl group, R is 1-4 carbon atom alkyl chain , X is selected from the group consisting of 1-16

carbon, branched or unbranched alkyl, substituted or unsubstituted aryl, and substituted
or unsubstituted diureidyl aryl with a reducing agent in an organic solvent at a
temperature in the range of 0-25 0C in an inert atmosphere, filtering the above said

reaction mixture to obtain the solid cake mass followed purification by known methods to obtain the ct. In an embodiment of the present invention the sugar used is selected from the group consisting of xylofuranose, arabinose, mannose and galactose.
In an another embodiment the organic solvent used is selected from the group consisting of diethyl ether, tetrahydrofuran, dioxane and a mixture thereof.

In yet another embodiment the reducing agent used is selected from the group consisting of lithium alumunium hydride, alkylated alumunium hydrides, tricetoxy borohydride, sodium borohydride and sodium cyanoborohydride.
In yet another embodiment ',N~- diglycosylated diaminoalcohol obtained comprising a group of compounds ',N3-di-II(SS)-deoxy-5-(2'-hydroxyethyl)-3-O-methyl- 1,2-0-isopropylidene-o-D-xylofuranos-5 -yl]- 1 ,3-diaminopropane, N' ,N3-di-II(SS/SR)-deoxy-5-(2' -hydroxyethyl)-3-O-methyl- 1 ,2-O-isopropylidene-a-D-xylofuranos-5-yl] -1,3-diaminopropane, 1, N3-di-[(SS)-deoxy-5-(2'-hydroxy ethyl)- 3-O-benzyl- 1,2-0-isopropylidene-x-D-xylofuranos- 5-yl]- 1 ,3-diaminopropane, N1, N3-di-II(5S/SR) -deoxy-5-(2 '-hydroxy ethyl)- 3-O-benzyl- 1 ,2-O-isopropylidene-cx-D-xylofuranos-5-yl]- 1,3-diaminopropane, 1, N7-di-[(SS)-deoxy-5-(2'-hydroxy ethyl)- 3-0-methyl- 1,2-0-isopropylidene-a-D-xylofuranos- 5 -yl]- 1 ,7-diaminoheptane, N', N7-di- [(5S/5R) -deoxy5-(2 '-hydroxy ethyl)- 3-0-methyl- 1 ,2-0-isopropylidene-cc-D-xylofuranos-5-yl] -1,7-diaminoheptane, 1, N7-di-[(5S)-deoxy-5-(2'-hydroxy ethyl)- 3-0-benzyl- 1,2-0-isopropylidene-a-D-xylofuranos-5-yl]- 1 ,7-diaminoheptane, N' ,N7-di-II(SS/SR)-deoxy-5-(2 '-hydroxy ethyl)- 3 -0-benzyl- 1 ,2-0-isopropylidene-x-D-xylofuranos-5-yl]- 1,7-diaminoheptane, 1, N'0-di-[(5S~-deoxy-5-(2'-hydroxy ethyl)- 3-0-methyl- 1,2-0-isopropylidene-a-D-xylofuranos-5-yl]- 1,1 0-diaminodecane, N' ,N'0-di-II(SS/SR) -deoxy5-(2 '-hydroxy ethyl)- 3-0-methyl- 1 ,2-0-isopropylidene-a-D-xylofuranos-5-yl] -1,10-diaminodecane, N', N '0-di-[(SS)-deoxy-5-(2 '-hydroxy ethyl)- 3-0-benzyl- 1,2-0-isopropylidene-cz-D-xylofuranos-5 -yl] -1,1 0-diaminodecane, N' ,N' 0 -di-Ij(SS/SR)-deoxy-5 -(2' -hydroxy ethyl)- 3 -0-benzyl- 1 ,2-0-isopropylidene-a-D-xylofuranos-5-yl] -1,10-

diaminodecane, N', N' 2 -di-[(5S)-deoxy-5-(2 '-hydroxy ethyl)- 3-0-methyl-i ,2-0-isopropylidene-a-D-xylofuranos-5-yl] -1,1 2-diaminododecane, N', N12-di-[(SS/SR)-deoxy-5 -(2 '-hydroxy ethyl)- 3-0-methyl- 1 ,2-0-isopropylidene-x-D-xylofuranos-5-yl] -

1,1 2-diaminododecane, N', N'2-di-[(SS)-deoxy-5-(2 '-hydroxy ethyl)-3-0-benzyl- 1,2-0-
isopropylidene-a-D-xylofuranos-5-yl]-1,12-diaminododecane, N, N -di- [(SS/SR)deoxy-5 - (2' -hydroxyethyl)- 3-0-benzyl- 1 ,2-0-isopropylidene-a-D-xylofuranos-5 -yl] -

1,1 2-diaminododecane, N, N -di-[5-deoxy-5-(2 -hydroxyethyl)- 1 ,2-0-isopropylidene-3 -

0-methyl-a-D-xylofuranos-5-yl] -1 ,4-phenylenediureide, N, N-di-[5-deoxy-5-(2 '-hydroxyethyl)- 1 ,2-0-isopropylidene-3-0-methyl-a-D-xylofuranos-5-yl]- 1,3-phenylenediureide, N, N -di-[5-deoxy-5-(2 ' -hydroxyethyl)- 1 ,2-O-isopropylidene-3-0-benzyl-a-D-xylofuranos-5-yl]- 1 ,3-phenylenediureide and N,N-di-115-deoxy-5-(2 '-hydroxyethyl)- 1 ,2-0-isopropylidene-3 -0-benzyl-o-D-xylofuranos-5-yl] -1,4-phenylenediureide.
In yet another embodiment of the present invention, the inert atmosphere used is selected from nitrogen and argon atmosphere.

The representative compounds of the formula 2 prepared by the process of the present invention are as follows

1. N' ,N3-di- [(SS)-deoxy-5-(2 '-hydroxy ethyl)- 3-0-methyl- 1 ,2-0-isopropy1idene-ct~-D-xylofuranos-5-yl]- 1 ,3-diaminopropane.

2. N',N3-di-II(SS/5R) -deoxy-5-(2'-hydroxy ethyl)- 3-0-methyl- 1,2-0-isopropylidene-x-D-xylofuranos-5-yl]- 1 ,3-diaminopropane.

3. N' ,N3-di- [(SS)-deoxy-5-(2 '-hydroxy ethyl)- 3 -0-benzyl- 1 ,2-0-isopropylidene-cL-D-xylofuranos-5-yl]- 1 ,3-diaminopropane.

4. N' ,N3-di- [(5S/SR) -deoxy-5-(2 -hydroxy ethyl)- 3 -0-benzyl- 1 ,2-0-isopropylidene-tx-D-xylofuranos-5-yl]-1 ,3-diaminopropane.

5. N' ,N7-di-[(SS)-deoxy-5-(2 '-hydroxy ethyl)- 3-0-methyl- 1 ,2-O-isopropylidene-cx-D-xylofuranos-5-yl]- 1 ,7-diaminoheptane.

6. N',N7-di-[(5S/5R) -deoxy-5-(2'-hydroxy ethyl)- 3-0-methyl- 1,2-0-isopropylidene-o~-D-xylofuranos-5-yl]- 1 ,7-diaminoheptane.
7. N',N7-di-[(SS)-deoxy-5-(2'-hydroxy ethyl)- 3-0-benzyl- 1 ,2-0-isopropylidene-a-D-xylofuranos-5-yl]- 1 ,7-diaminoheptane.

8. N' ,N7-di-[(5S/5R)-deoxy-5-(2 '-hydroxy ethyl)- 3-0-benzyl- 1 ,2-0-isopropylidene-a-D-xylofuranos-5-yl]- 1 ,7-diaminoheptane.

9. N' ,N'0-di-[(SS)-deoxy-5-(2 '-hydroxy ethyl)- 3-0-methyl- 1 ,2-0-isopropylidene-a-D-xylofuranos-5-yl]- 1,1 0-diaminodecane.
10. N',N'0-di-[(SS/5R) -deoxy-5-(2'-hydroxy ethyl)- 3-0-methyl- 1 ,2-0-isopropylidene-a-D-xylofuranos-5-yl]- 1,1 0-diaminodecane.

11. N' ,N'0-di-[(SS)-deoxy-5-(2'-hydroxy ethyl)- 3-0-benzyl- 1,2-0-isopropylidene-cx-D-xylofuranos-5-yl]- 1, 10-diaminodecane.
12. N' ,N'0-di-[(SS/SR)-deoxy-5-(2 -hydroxy ethyl)- 3 -0-benzyl- 1 ,2-0-isopropylidene-x-D-xylofuranos-5 -yl] -1,1 0-diaminodecane.
13. N' ,N12-di-[(5S)-deoxy-5-(2 -hydroxy ethyl)- 3-0-methyl- 1 ,2-0-isopropylidene-a-D-xylofuranos-5-yl]- 1,1 2-diaminododecane.
14. N1 ,N' 2-di-II(SS/5R)-deoxy-5 -(2' -hydroxy ethyl)- 3-0-methyl- 1 ,2-0-isopropylidene-c-D-xylofuranos-5-yl]- 1, 12-diaminododecane.
15. N' ,N'2-di-[(5S)-deoxy-5-(2 ' -hydroxy ethyl)- 3-0-benzyl- 1 ,2-0-isopropylidene-a-D-xylofuranos-5-yl]-1 , 12-diaminododecane.
16. N1 ,N' 2-di-II(SS/5R)-deoxy-5-(2 -hydroxy ethyl)- 3 -0-benzyl- 1 ,2-O-isopropylidene-a-D-xylofuranos-5-yl] -1,1 2-diaminododecane.
17. N,N -di-[5-deoxy-5 -(2' -hydroxyethyl)- 1 ,2-0-isopropylidene-3-O-methyl-cx-D-xylofuranos-5-yl]- 1 ,4-phenylenediureide.
18. N,N-di-[5-deoxy-5-(2 '-hydroxyethyl)- 1 ,2-0-isopropylidene-3-O-methyl-o-D-xylofuranos-5-yl]- 1 ,3-phenylenediureide.
19. N,N-di-[5-deoxy-5-(2 '-hydroxyethyl)- 1 ,2-0-isopropylidene-3-0-benzyl-a-D-xylofuranos-5-yl]- 1 ,3-phenylenediureide.
20. N,N-di-[5-deoxy-5-(2 -hydroxyethyl)- 1 ,2-0-isopropylidene-3 -O-benzyl-cx-Dxylofuranos-5-yl]- 1 ,4-phenylenediureide.
The following examples are given by the way of illustration and should not be construed to limit the scope of the invention.

Example-1

N' ,N3-di-[(5S)-deoxy-(-(2 '-hydroxyethyl)-1,2-O-isopropylidene-3-O-methyl-a-D-xylofuranos-5-ylJ -i ,3-diaminopropane(1)
A slurry of lithium alumunium hydride (0.016 g, 0.42 immol) in anhydrous tetrahydrofuran (15 ml) was magnetically stirred at 0 0C for 15 minutes under nitrogen atmosphere. To the stirring reaction mixture a solution of N' ,N3-di-[5-carbethoxymethyl-5 S-deoxy- 1 ,2-0-isopropylidene-3 -0-methyl-a-D-xylofuranos-5-yl] -diaminopropane(1, 0.250g, 0.4045 mmol), in anhydrous tetrahydrofuran (10 ml) was added slowly during 15 mm at 0 0C. The reaction mixture stirred at the same temperature for V2 hr followed by stirring at 25 0C for 1.5 hr. The reaction mixture was quenched by adding an aqueous solution of 5% sodium hydroxide and saturated aqueous solution of sodium sulphate. After ½ hr reaction mixture filtered and the solid cake was washed with more THF. The combined organic layer evaporated under reduced pressure and the crude product was dissolved in ethyl acetate and washed with water. The organic layer dried (Na2SO4) and evaporated under reduced pressure to a get a crude mass which was purified by conventional methods to give the title compound 1 as colourless oil. FABMS:

m!z = 535(M+H)~


Example-2

N' ,N3-di-j(5RIS)-deoxy-5-(2 '-hydroxyethyl)-1 ,2-O-isopropylidene-3-O-methyl--a-D-

xylofuranos-5-ylJ -1,3-diaminoproane(2):

A slurry of lithium alumunium hydride (0.007 g, 0.0842 mmol) in anhydrous

tetrahydrofuran (10 ml) was magnetically stirred at 0 0C for 15 minutes under nitrogen atmosphere. To the stirring reaction mixture a solution of N' ,N3-di-[5-carbethoxymethyl-5-deoxy- 1 ,2-0-isopropylidene-3-0-methyl--a-D-xylofuranos-5 -yl] -1,3 -diaminopropane(0.1 10 g, 0.178 mmol), in anhydrous tetrahydrofuran (10 ml) was added slowly during 15 mm at 0 0C. The reaction mixture stirred at the same temperature for 'A hr followed by stirring at 25 0C for 1.5 hr. Excess of reducing agent was quenched by adding an aqueous solution of 5% sodium hydroxide and saturated aqueous solution of sodium sulphate. After ½ hr reaction mixture filtered and the solid cake was washed with more THF. The combined organic layer evaporated under reduced pressure and the crude product was dissolved in ethyl acetate and washed with water. The organic layer dried (Na2SO4) and evaporated under reduced pressure to a get a crude mass, which was purified by conventional methods to give the title compound 2 as colourless oil. FABMS:

m/z = 535(M+H)~

Example-3

N' ,N3-di-[3-O-benzyl-(5S)-deoxy-5-(2 '-hydroxyethyl)-1,2-O-isopropylidene-cc-D-xylofuranos-5-ylJ-1,3-diaminopropane(3):

A slurry of lithium alumunium hydride (0.007 g, 0.1842 mmol) in anhydrous tetrahydrofuran (10 ml) was magnetically stirred at 0 0C for 15 minutes under nitrogen atmosphere. To the stirring reaction mixture a solution of N',N3-di-113-0-benzyl 5-


carbethoxymethyl-5-deoxy- 1 ,2-O-isopropylidene-o~-D-xylofuranos-5-yl]-diaminopropane(1, 0.140 g, 0.182 mmol), in anhydrous tetrahydrofuran (10 ml) was added slowly during 15 mm at 0 0C. The reaction mixture stirred at the same temperature for ½ hr followed by stirring at 25 0C for 1.5 hr. Excess of reducing agent was quenched by adding an aqueous solution of 5 % sodium hydroxide and saturated aqueous solution of sodium sulphate. After '/2 hr reaction mixture filtered and the solid cake was washed with more THF. The combined organic layer evaporated under reduced pressure and the crude product was dissolved in ethyl acetate and washed with water. The organic layer dried (Na2SO4) and evaporated under reduced pressure to a get a crude mass, which was purified by conventional methods to give the title compound 3 as colourless oil. FABMS:

m/z = 687(M+H)~

Example 4

N ,N3-di-13-O-benzyl (5R/S)-deoxy-5-(2 '-hydroxyethyl)-1,2-O-isopropylidene-a-D-xylofuranos-5-yl]-1,3-diaminopropane (4):

A slurry of lithium alumunium hydride (0.006g, 0.1579 mmol) in anhydrous tetrahydrofuran (1 Oml) was magnetically stirred at 0 0C for 15 minutes under nitrogen atmosphere. To the stirring reaction mixture a solution of N1,N3-di-[5-carbethoxymethyl-5(R/S)-deoxy- 1 ,2-O-isopropylidene-3-O-benzyl-a-D-xylofuranos-5-yl] -diaminopropane(1, 0.120 g, 0.1558 mmol), in anhydrous tetrahydrofuran (10 ml) was added slowly during 15 mm at 0 0C. The reaction mixture stirred at the same temperature for ½ hr followed by stirring at 25 0C for 1.5 hr. Excess of reducing agent was quenched by adding an aqueous solution of 5% sodium hydroxide and saturated aqueous solution of sodium sulphate. After ½ hr reaction mixture filtered and the solid cake was washed with
more THF. The combined organic layer evaporated under reduced pressure and the crude product was dissolved in ethyl acetate and washed with water. The organic layer dried (Na2SO4) and evaporated under reduced pressure to a get a crude mass, which was purified by conventional methods to give the title compound 4 as colourless oil. FABMS:

m/z = 687(M+H)~

Example-5

N'-,N7-di-I(5S)-(2 '-hydroxyethyl)-5-deoxy-i ,2-O-isopropylidene-3-O-methyl-a-D-xylofuranosylj-1,7-diaminoheptane(5):

A slurry of lithium alumunium hydride (0.023 g, 0.6053 mmol) in anhydrous tetrahydrofuran (15 ml) was magnetically stirred at 0 0C for 15 minutes under nitrogen atmosphere. To the stirring reaction mixture a solution of N1 ,N7-di-115-carbethoxymethyl-5(S)-deoxy- 1 ,2-O-isopropylidene-3-O-methyl--x-D-xylofuranos-5-yl] -1,7-diaminoheptane(1, 0.40 g, 0.155 mmol), in anhydrous tetrahydrofuran (10 ml) was added slowly during 15 mm at 0 0C. The reaction mixture stirred at the same temperature for ½hr followed by stirring at 25 0C for 1.5 hr. Excess of reducing agent was quenched by adding an aqueous solution of 5% sodium hydroxide and saturated aqueous solution of sodium sulphate. After ½ hr reaction mixture filtered and the solid cake was washed with more THF. The combined organic layer evaporated under reduced pressure and the crude product was dissolved in ethyl acetate and washed with water. The organic layer dried (Na2SO4) and evaporated under reduced pressure to a get a crude mass, which was purified by conventional methods to give the title compound 5 as colourless oil. FABMS:

m/z = 591(M+H)~
Example-6

N'-,N7-di-I(5R/S)-(2 '-hydroxyethyl)-5-deoxy-1,2-O-isopropylidene-3-O-methyl-ct-D-

xylofuranosylj-1,7-diaminoheptane(6):

A slurry of lithium alumunium hydride (0.026 g, 0.6842 mmol) in anhydrous tetrahydrofuran (10 ml) was magnetically stirred at 0 0C for 15 minutes under nitrogen atmosphere. To the stirring reaction mixture a solution of N' ,N7-di-[5-carbethoxymethyl-5(R/S)-deoxy- 1 ,2-O-isopropylidene-3 -O-methyl--a-D-xylofuranos-5-yl] -1,7-diaminoheptane(i, 0.46 g, 0.6842 mmol), in anhydrous tetrahydrofuran (10 ml) was added slowly during 15 mm at 0 0C. The reaction mixture stirred at the same temperature for ½ hr followed by stirring at 25 0C for 1.5 hr. Excess of reducing agent was quenched by adding an aqueous solution of 5% sodium hydroxide and saturated aqueous solution of sodium sulphate. After ½ hr reaction mixture filtered and the solid cake was washed with more THF. The combined organic layer evaporated under reduced pressure and the crude product was dissolved in ethyl acetate and washed with water. The organic layer dried (Na2SO4) and evaporated under reduced pressure to a get a crude mass, which was purified by conventional methods to give the title compound 5 as colourless oil. FABMS:

mlz = 591 (M+H)~

Example-7

N1-,N7-di-j(5S)-(2 '-hydroxyethyl)-5-deoxy-1,2-O-isopropylidene-3-O-benzyl-a-D-xylofuranosylJ-1,7-diaminoheptane(7):

A slurry of lithium alumunium hydride (0.0 12 g, 0.3 158 mmol) in anhydrous tetrahydrofuran (10 ml) was magnetically stirred at 0 0C for 15 minutes under nitrogen atmosphere. To the stirring reaction mixture a solution of N' ,N7-di-[5-carbethoxymethyl-

5(S)-deoxy- 1 ,2-O-isopropylidene-3-O-benzyl-ct-D-xylofuranos-5-yl]- 1,7-diaminoheptane(1, 0.260 g, 0.3148 mmol), in anhydrous tetrahydrofuran (10 ml) was added slowly during 15 mm at 0 0C. The reaction mixture stirred at the same temperature for ½ hr followed by stirring at 25 0C for 1.5 hr. Excess of reducing agent was quenched by adding an aqueous solution of 5% sodium hydroxide and saturated aqueous solution of sodium sulphate. After ½ hr reaction mixture filtered and the solid cake was washed with more THF. The combined organic layer evaporated under reduced pressure and the crude product was dissolved in ethyl acetate and washed with water. The organic layer dried (Na2SO4) and evaporated under reduced pressure to a get a crude mass, which was purified by conventional methods to give the title compound 7 as colourless oil. FABMS:

m/z = 743(M+H)~

Example-8

N'-,N7-di-I(5RIS)-(2 '-hydroxyethyl)-5-deoxy-1 ,2-O-isopropylidene-3-O-benzyl-a-D-xylofuranosyll-1 ,7-diaminoheptane(8):

A slurry of lithium alumunium hydride (0.007 g, 0.1842 mmol) in anhydrous tetrahydrofuran (10 ml) was magnetically stirred at 0 0C for 15 minutes under nitrogen atmosphere. To the stirring reaction mixture a solution of N' ,N7-di-II5-carbethoxymethyl-5(S)-deoxy- 1 ,2-O-isopropylidene-3 -O-benzyl-a-D-xylofuranos-5-yl]- 1,7-diaminoheptane(1, 0.14 g, 0.1695 mmol), in anhydrous tetrahydrofuran (10 ml) was added slowly during 15 mm at 0 0C. The reaction mixture stirred at the same temperature for ½ hr followed by stirring at 25 0C for 1.5 hr. Excess of reducing agent was quenched by adding an aqueous solution of 5% sodium hydroxide and saturated aqueous solution of sodium sulphate. After ½ hr reaction mixture filtered and the solid cake was washed with
more THF. The combined organic layer evaporated under reduced pressure and the crude product was dissolved in ethyl acetate and washed with water. The organic layer dried (Na2SO4) and evaporated under reduced pressure to a get a crude mass, which was purified by conventional methods to give the title compound 8 as colourless oil. FABMS:

m/z = 743 (M+H)~

Example-9

N' -,N'0-di- I(5S)-(2 '-hydroxyethyl)-5-deoxy-1,2-O-isopropylidene-3-O-methyl-cc-D-xylofuranosylJ-1 ,1O-diaminodecane(9):

A slurry of lithium alumunium hydride (0.0 17 g, 0.4474 mmol) in anhydrous tetrahydrofuran (10 ml) was magnetically stirred at 0 0C for 15 minutes under nitrogen atmosphere. To the stirring reaction mixture a solution of N' ,N'0-di-II5-carbethoxymethyl-5(S)-deoxy- 1 ,2-O-isopropylidene-3 -O-methyl-a-D-xylofuranos-5 -yl]1,1O-diaminodecane(1, 0.3 15 g, 0.44 mmol), in anhydrous tetrahydrofuran (10 ml) was added slowly during 15 mm at 0 0C. The reaction mixture stirred at the same temperature for ½ hr followed by stirring at 25 0C for 1.5 hr. Excess of reducing agent was quenched by adding an aqueous solution of 5% sodium hydroxide and saturated aqueous solution of sodium sulphate. After ½ hr reaction mixture filtered and the solid cake was washed with more THF. The combined organic layer evaporated under reduced pressure and the crude product was dissolved in ethyl acetate and washed with water. The organic layer dried (Na2SO4) and evaporated under reduced pressure to a get a crude mass, which was purified by conventional methods to give the title compound 9 as colourless oil. FABMS:

mIz=633(M+H)~
Example-i 0

N'-,N'0-di-[(SR/S)-(2 '-hydroxyethyl)-5-deoxy-i ,2-O-isopropylidene-3-O-methyl-cc-D-

xylofuranosylj-1 ,10-diaminodecane(iO):

A slurry of lithium alumunium hydride (0.02 1 g, 0.5526 mmol) in anhydrous tetrahydrofuran (15 ml) was magnetically stirred at 0 0C for 15 minutes under nitrogen atmosphere. To the stirring reaction mixture a solution of N' ,N'0-di-[5-carbethoxymethyl-5(R/S)-deoxy- 1 ,2-O-isopropylidene-3-O-methyl-a-D-xylofuranos-5-yl]-l,l0-diaminodecane(1, 0.39 g, 0.5447 mmol), in anhydrous tetrahydrofuran (10 ml) was added slowly during 15 mm at 0 0C. The reaction mixture stirred at the same temperature for ½ hr followed by stirring at 25 0C for 1.5 hr. Excess of reducing agent was quenched by adding an aqueous solution of 5% sodium hydroxide and saturated aqueous solution of sodium sulphate. After ½ hr reaction mixture filtered and the solid cake was washed with more THF. The combined organic layer evaporated under reduced pressure and the crude product was dissolved in ethyl acetate and washed with water. The organic layer dried (Na2SO4) and evaporated under reduced pressure to a get a crude mass, which was purified by conventional methods to give the title compound 10 as colourless oil. FABMS: m/z = 633(M+H)~

Example-li

N1-,N'0-di-[(5S)-(2'-hydroxyethyl)-5-deoxy-1 ,2-O-isopropylidene-3-O-benzyl-a-D-xylofuranosylj-i,1 0-diaminodecane(1 1):

A slurry of lithium alumunium hydride (0.019 g, 0.50 mmol) in anhydrous tetrahydrofuran (10 ml) was magnetically stirred at 0 0C for 15 minutes under nitrogen atmosphere. To the stirring reaction mixture a solution of 1,N ' 0-di-115-
carbethoxymethyl-5(S)-deoxy- 1 ,2-O-isopropylidene-3 -O-benzyl-cx-D-xylofuranos-5-yl] -1,10-diaminodecane(i, 0.42 g, 0.4839 mmol), in anhydrous tetrahydrofuran (10 ml) was added slowly during 15 mm at 0 0C. The reaction mixture stirred at the same temperature for ½ hr followed by stirring at 25 0C for 1.5 hr. Excess of reducing agent was quenched by adding an aqueous solution of 5% sodium hydroxide and saturated aqueous solution of sodium sulphate. After ½ hr reaction mixture filtered and the solid cake was washed with more THF. The combined organic layer evaporated under reduced pressure and the crude product was dissolved in ethyl acetate and washed with water. The organic layer dried (Na2SO4) and evaporated under reduced pressure to a get a crude mass, which was purified by conventional methods to give the title compound ii as colourless oil. FABMS: m!z = 785(M+H)~

Example-i2

N'-,N10-di-I(5R/S)-(2 '-hydroxyethyl)-5-deoxy- i,2-O-isopropylidene-3-O-benzyl-a-D-xylofuranosylJ-i ,10-diaminodecane(i2):

A slurry of lithium alumunium hydride (0.011 g, 0.2895 mmol) in anhydrous tetrahydrofuran (10 ml) was magnetically stirred at 0 0C for 15 minutes under nitrogen atmosphere. To the stirring reaction mixture a solution of N',N10-di-[5-carbethoxymethyl-5(RIS)-deoxy- 1 ,2-O-isopropylidene-3-O-benzyl-c~-D-xylofuranos-5-

yl]-1,l0-diaminodecane(i, 0.25 g, 0.288 mmol), in anhydrous tetrahydrofuran (10 ml) was added slowly during 15 mm at 0 0C. The reaction mixture stirred at the same temperature for ½ hr followed by stirring at 25 0C for 1.5 hr. Excess of reducing agent was quenched by adding an aqueous solution of 5% sodium hydroxide and saturated aqueous solution of sodium sulphate. After ½ hr reaction mixture filtered and the solid

cake was washed with more THF. The combined organic layer evaporated under reduced pressure and the crude product was dissolved in ethyl acetate and washed with water. The organic layer dried (Na2SO4) and evaporated under reduced pressure to a get a crude mass, which was purified by conventional methods to give the title compound i2 as colourless oil. FABMS: m/z = 785(M+H)~


Example-i3


N1,N'2-di- I -(5S)-(2 '-hydroxyethyl)-5-deoxy-i ,2-O-isopropylidene-3-O-methyl -a-Dxylo furanos-5-ylI-i,i 2-diaminododecane(i3):


A slurry of lithium alumunium hydride (0.088 g, 2. 3158 mmol) in anhydrous tetrahydrofuran (15 ml) was magnetically stirred at 0 0C for 15 minutes under nitrogen atmosphere. To the stirring reaction mixture a solution of N',N'2-di-[5-carbethoxymethyl-5 (S)-deoxy- 1 ,2-O-isopropylidene-3-O-methyl-cL-D-xylofuranos-5-yl] -1,12-diaminododecane(i, l.72g, 2.3118 mmol), in anhydrous tetrahydrofuran (10 ml) was added slowly during 15 mm at 0 0C. The reaction mixture stirred at the same temperature for ½ hr followed by stirring at 25 0C for 1.5 hr. Excess of reducing agent was quenched by adding an aqueous solution of 5% sodium hydroxide and saturated aqueous solution of sodium sulphate. After ½ hr reaction mixture filtered and the solid cake was washed with more THF. The combined organic layer evaporated under reduced pressure and the crude product was dissolved in ethyl acetate and washed with water. The organic layer dried (Na2SO4) and evaporated under reduced pressure to a get a crude mass, which was purified by conventional methods to give the title compound i3 as colourless oil. FABMS: m/z = 661(M+H)~

Example-i4

',N '2-di-j (5S)-(2 '-hydroxyethyl)-5-deoxy-i,2-O-isopropylidene-3-O-methyl -cc-D

xylo furanos-5-yl]-i,i2-diaminododecane(i4):

A slurry of lithium alumunium hydride (0.035 g, 0.9240 mmol) in anhydrous

tetrahydrofuran (15 ml) was magnetically stirred at 0 0C for 15 minutes under nitrogen atmosphere. To the stirring reaction mixture a solution of N1,N'2-di-II5-carbethoxymethyl-5(R/S)-deoxy- 1 ,2-O-isopropylidene-3-O-methyl-c~-D-xylofuranos-5-yl]-l,12-diaminododecane(i, 0.68g, 0.9210 mmol), in anhydrous tetrahydrofuran (10 ml) was added slowly during 15 mm at 0 0C. The reaction mixture stirred at the same temperature for ½ hr followed by stirring at 25 0C for 1.5 hr. Excess of reducing agent was quenched by adding an aqueous solution of 5% sodium hydroxide and saturated aqueous solution of sodium sulphate. After ½ hr reaction mixture filtered and the solid cake was washed with more THF. The combined organic layer evaporated under reduced pressure and the crude product was dissolved in ethyl acetate and washed with water. The organic layer dried (Na2SO4) and evaporated under reduced pressure to a get a crude mass, which was purified by conventional methods to give the title compound 14 as colourless oil. FABMS: m/z = 661(M+H)~

Example-iS

N' ,N'2-di-13-O-benzyl-(5S)-(2'-hydroxyethyl)-5-deoxy-i,2-O-isopropylidene-a-D-xylo furanos-5-ylI-i,i2-diaminododecane(i 5):

A slurry of lithium alumunium hydride (0.026 g, 0.6842 mmol) in anhydrous tetrahydrofuran (15 ml) was magnetically stirred at 0 0C for 15 minutes under nitrogen atmosphere. To the stirring reaction mixture a solution of N',N'2-di-[5-

carbethoxymethyl-5(S)-deoxy- 1 ,2-O-isopropylidene-3-O-benzyl-a-D-xylofuranos-5 -yl]1,12-diaminododecane(i, 0.6 g, 0.6696 mmol), in anhydrous tetrahydrofuran (10 ml) was added slowly during 15 mm at 0 0C. The reaction mixture stirred at the same temperature for ½ hr followed by stirring at 25 0C for 1.5 hr. Excess of reducing agent was quenched by adding an aqueous solution of 5% sodium hydroxide and saturated aqueous solution of sodium sulphate. After ½ hr reaction mixture filtered and the solid cake was washed with more THF. The combined organic layer evaporated under reduced pressure and the crude product was dissolved in ethyl acetate and washed with water. The organic layer dried (Na2SO4) and evaporated under reduced pressure to a get a crude mass, which was purified by conventional methods to give the title compound i5 as colourless oil. FABMS: m/z = 813(M+H)~


N',N12-di- [3-O-benzyl-(5R/ST~-(2 '-hydroxyethyl)-5-deoxy-i ,2-O-isopropylidene-a-D-

xylo furanos-5-yl]-i,i2-diaminododecane(i6):

A slurry of lithium alumunium hydride (0.0 14 g, 0.357 1 mmol) in anhydrous

tetrahydrofuran (15 ml) was magnetically stirred at 0 0C for 15 minutes under nitrogen atmosphere. To the stirring reaction mixture a solution of N',N12-di-115-carbethoxymethyl-5 (RIS)-deoxy- 1 ,2-O-isopropylidene-3 -O-benzyl-a-D-xylofuranos-5-yl]-l,12-diaminododecane(i, 0.32 g, 0.3571 mmol), in anhydrous tetrahydrofuran (10 ml) was added slowly during 15 mm at 0 0C. The reaction mixture stirred at the same temperature for ½ hr followed by stirring at 25 0C for 1.5 hr. Excess of reducing agent was quenched by adding an aqueous solution of 5% sodium hydroxide and saturated aqueous solution of sodium sulphate. After ½ hr reaction mixture filtered and the solid cake was washed with more THF. The combined organic layer evaporated under reduced
pressure and the crude product was dissolved in ethyl acetate and washed with water. The organic layer dried (Na2SO4) and evaporated under reduced pressure to a get a crude mass, which was purified by conventional methods to give the title compound i6 as colourless oil. FABMS: m/z = 8l3(M+H)~


Example-i 7


N,N'-di-I(5S)-deoxy-5-(2 '-hydroxyethyl)-1,2-O-isopropylidene-3-O-methyl--cc-D-xylofuranos-5-ylJ-i,4-phenylenediureide (i7):


A slurry of lithium alumunium hydride (0.042 g, 1.12 mmol) in anhydrous tetrahydrofuran (20 ml) was magnetically stirred at 0 0C for 15 minutes under nitrogen atmosphere. To the stirring reaction mixture a solution of N, N-di-[5-carbethoxymethyl-5-deoxy- 1 ,2-O-isopropylidene-3 -O-methyl-a-D-xylofuranos-5 -yl]- 1,4-phenylenediureide(i, 0.8 g, 1 .O84mmol), in anhydrous tetrahydrofuran (10 ml) was added slowly during 15 mm at 0 0C. The reaction mixture stirred at the same temperature for ½hr followed by stirring at 25 0C for 1.5 hr. Excess of reducing agent was quenched by adding an aqueous solution of 5% sodium hydroxide and saturated aqueous solution of sodium sulphate. After ½ hr reaction mixture filtered and the solid cake was washed with more THF. The combined organic layer evaporated under reduced pressure and the crude product was dissolved in ethyl acetate and washed with water. The organic layer dried (Na2SO4) and evaporated under reduced pressure to a get a crude mass, which was purified by conventional methods to give the title compound i7 as colourless foam. FABMS: m/z = 655(M+H)~

Example-i 8

N,N'-di-I(5S)-deoxy-5-(2 '-hydroxyethyl)-1,2-O-isopropylidene-3-O-methyl--a-D-

xylofuranos-5-ylJ-i,4-phenylenediureide (18):

A slurry of lithium alumunium hydride (0.042 g, 1.12 mmol) in anhydrous tetrahydrofuran (20 ml) was magnetically stirred at 0 0C for 15 minutes under nitrogen atmosphere. To the stirring reaction mixture a solution of N, N -di- ES-carbethoxymethyl5-deoxy- 1 ,2-O-isopropylidene-3 -O-methyl-a-D-xylofuranos-5-yl] -1,4-phenylenediureide(i, 0.8 g, 1 .O84mmol), in anhydrous tetrahydrofuran (10 ml) was added slowly during 15 mm at 0 0C. The reaction mixture stirred at the same temperature for ½hr followed by stirring at 25 0C for 1.5 hr. Excess of reducing agent was quenched by adding an aqueous solution of 5% sodium hydroxide and saturated aqueous solution of sodium sulphate. After ½ hr reaction mixture filtered and the solid cake was washed with more THF. The combined organic layer evaporated under reduced pressure and the crude product was dissolved in ethyl acetate and washed with water. The organic layer dried (Na2SO4) and evaporated under reduced pressure to a get a crude mass, which was purified by conventional methods to give the title compound i8 as colourless foam. FABMS: m/z = 655(M+H)~

Example-i9

N,N'-di-[(5S)-deoxy-5-(2 '-hydroxyethyl)-i,2-O-isopropylidene-3-O-benzyl--cc-D-xylofuranos-5-ylJ-i,4-phenylenediureide (i9):

A slurry of lithium alumunium hydride (0.042 g, 1.12 mmol) in anhydrous tetrahydrofuran (20 ml) was magnetically stirred at 0 0C for 15 minutes under nitrogen atmosphere. To the stirring reaction mixture a solution of N, N-di-[5-carbethoxymethyl-

5-deoxy- 1 ,2-O-isopropylidene-3-O-benzyl-a-D-xylofuranos-5-yl]- 1,4-phenylenediureide(i, 0.996 g, 1.12 mmol), in anhydrous tetrahydrofuran (10 ml) was added slowly during 15 mm at 0 0C. The reaction mixture stirred at the same temperature for ½ hr followed by stirring at 25 0C for 1.5 hr. Excess of reducing agent was quenched by adding an aqueous solution of 5% sodium hydroxide and saturated aqueous solution of sodium sulphate. After ½ hr reaction mixture filtered and the solid cake was washed with more THF. The combined organic layer evaporated under reduced pressure and the crude product was dissolved in ethyl acetate and washed with water. The organic layer dried (Na2SO4) and evaporated under reduced pressure to a get a crude mass, which was purified by conventional methods to give the title compound i4 as colourless foam. FABMS: m/z = 807(M+H)~

Example- 20

N,N'-di-13-O-benzyl-5-deoxy-5-(2 '-hydroxyethyl)-i ,2-O-isopropylidene-xylofuranos-5-ylJ-i ,3-phenylenediureide (20):

A slurry of lithium alumunium hydride (0.042 g, 1.12 mmol) in anhydrous tetrahydrofuran (20 ml) was magnetically stirred at 0 0C for 15 minutes under nitrogen atmosphere. To the stirring reaction mixture a solution of N,N-di-II5-carbethoxymethyl-5-deoxy- 1 ,2-O-isopropylidene-3-O-benzyl--a-D-xylofuranos-5-yl] -1,3-phenylenediureide(l, 0.995 g, 1.12 mmol), in anhydrous tetrahydrofuran (10 ml) was added slowly during 15 mm at 0 0C. The reaction mixture stirred at the same temperature for ½ hr followed by stirring at 25 0C for 1.5 hr. Excess of reducing agent was quenched by adding an aqueous solution of 5% sodium hydroxide and saturated aqueous solution of sodium sulphate. After ½ hr reaction mixture filtered and the solid cake was washed with

more THF. The combined organic layer evaporated under reduced pressure and the crude product was dissolved in ethyl acetate and washed with water. The organic layer dried (Na2SO4) and evaporated under reduced pressure to a get a crude mass, which was purified by conventional methods to give the title compound 16 as colourless foam. FABMS: m!z = 807(M+H)~






The representative compounds of the formula 2 prepared by the process of the present invention are as follows
The invention is illustrated by the following examples, which in no way

represent a limitation thereof.
Example-2 i



For MABA assay M tuberculosis H37Ra was used as a suitable surrogate for the virulent 1137 Rv strain. 7-8 days old cultures were diluted in liquid medium to provide an optimal density of 0.02 at 550 nm spectrophotometrically which gave colour change of Alamar blue 'oxidation reduction' dye (blue to pink). The standard antitubercular agents Rifamycin, isoniazid, p-aminosalicylic acid, ethambutol and ethionamide were taken as positive controls. (Collins, L.A.; Franzblan, S.G.; Antimicrob. Agents Chemotlier. 1997, 41, 1004. The antitubercular activities determined by this method are given in table-i


Table-i: In vitro Antitubercular activity using MABA technique:
(Table Removed)
Example-22

In agar microdilution method serial two fold dilutions of each test compound was added into 7H10 agar and M. tuberculosis 1137 Rv was used as test organism. The test was performed as reported by Saita et.al. (Saita, H.; Tomioka, H.; Sato, K.; Yamne, T.; Yamashita, K.; Hosol, K. Antimicrob. Agents Chemother. 1991, 35, 542. The antitubercular activities are given in Table-2


Table-2: In vitro antitubercular activity

(Table Removed)
Example- 23

The activity of compounds was also tested against bioluminiscent Mycobacterium aurum expressingfirefly luciferase (D.K.Deb; K.K.Srivastava; Ranjana Srivastava; and B.S. Srivastava Biochem. Biophys. Res. Comm. 279, 457-6 1, 2000). The cells were grown to an optical density of 0.03 at 600 nm. Two fold dilutions of compounds were prepared and added to 100~tl culture (A600 = 0.03) in microtitre plate. The plate was incubated at 37 0C for 6 hr and bioluminiscence was measured for each well. Two controls (with no drug) and two standard drugs (rifampicin and sparfioxacin) were also included. For measurement of bioluminescence lOOpi of culture was mixed with 250 ~l of sodium citrate buffer (0.1M, pH 5.0) in the tube and was placed in the luminometer. (Lumat LB

9507- EG & G Berthhold) lOOpi of 1 mM luciferase substrate was infected and luminescence was measured as relative light units (RLU) for 1 Os. The antitubercular activities of the compounds are given in Table-2 and Table-3




We claim

1. A process for the preparation novel N',N~-diglycosylated diaminoalcohols of the general formula 2,
(Formula Removed)
wherein R1 is selected from 1-4 carbon atom alkyl chain and aralkyl group, X is selected from the group consisting of 1-16 carbon, branched or unbranched alkyl, substituted or unsubstituted alkyl and aryl and substituted or unsubstituted diureidyl aryl, useful as antitubercular agent which comprises reducing gicosyl amino ester of formula 1, wherein R1 is selected from group consisting of 1-4 carbon atom alkyl chain and aralkyl group, R is 1-4 carbon atom alkyl chain , X is selected from the group consisting of 1-16 carbon, branched or unbranched alkyl, substituted or unsubstituted aryl, and substituted or unsubstituted diureidyl aryl with a reducing agent in an organic solvent at a temperature in the range of 0-25 0C in an inert atmosphere, filtering the above said reaction mixture to obtain the solid cake mass followed purification by known methods to obtain the desired product.
2. A process as claimed in claim 1 where the sugar used is selected from a group consisting of xylofiiranose, arabinose, mannose and galactose.
3. A process as claimed in claims 1&2, wherein the organic solvent used is selected from the group consisting of diethyl ether, tetrahydrofuran, dioxane and a mixture

thereof.

4. A process as claimed in claims 1-3, wherein the reducing agent used is selected from the group consisting of lithium alumunium hydride, 3lkylated alumunium hydrides, tricetoxy borohydride, sodium borohydride and sodium cyanoborohydride.

5. A process as claimed in claims 1-3, wherein the inert atmosphere used is nitrogen or organ.
6. A process as claimed in claims 1-5, wherein the compound N',N~- diglycosylated diaminoalcohol obtained comprising a group of compounds N',N3-di-II(SS)-deoxy-5-(2 '-hydroxyethyl)-3-0-methyl- 1 ,2-O-isopropylidene-cL-D-xylofuranos-5-yl]- 1,3 -diaminopropane, N' ,N3 -di-[(SS/SR)-deoxy-5 -(2' -hydroxyethyl)-3 -0-methyl-i ,2-0-isopropylidene-cL-D-xylofuranos-5-yl]- 1 ,3-diaminopropane, N', N3-di-[(SS)-deoxy-5-(2 '-hydroxy ethyl)- 3-0-benzyl- 1 ,2-0-isopropylidene-a-D-xylofuranos-5-yl]- 1,3 -diaminopropane, N', N3-di-II(5S/SR) -deoxy-5-(2 '-hydroxy ethyl)- 3 -0-benzyl- 1 ,2-0-isopropylidene-a-D-xylofuranos-5-yl]- 1,3 -diaminopropane, N1, N7-di-[(SS)-deoxy-5-(2'-hydroxy ethyl)- 3-0-methyl- 1,2-0~isopropylidene-ct-D-xy1ofuranos-5-yl] -1 ,7-diaminoheptane, I, N7-di-II(SS/5R)

-deoxy-5-(2'-hydroxy ethyl)- 3-0-methyl- 1 ,2-0-isopropylidene-a-D-xylofuranos-5-yl]- 1 ,7-diaminoheptane, N', N7-di-II(5S)-deoxy-5-(2 -hydroxy ethyl)- 3 -0-benzyl- 1 ,2-0-isopropylidene-a-D-xylofuranos-5-yl]- 1,7-diaminoheptane, N' ,N7-di-I~SS/SR)-deoxy-5-(2 -hydroxy ethyl)- 3 -0-benzyl- 1,2-

0-isopropylidene-a-D-xylofuranos-5 -yl] -1 ,7-diaminoheptane, N', N'0-di-[(SS)-deoxy-5-(2 '-hydroxy ethyl)- 3-0-methyl- 1 ,2-0-isopropylidene-cc-D-xylofuranos-~-yl]- 1,1 0-diaminodecane, N' ,N' 0-di-II(5S/5R) -deoxy-5-(2 '-hydroxy ethyl)- 3-0-methyl- 1 ,2-0-isopropylidene-a-D-xylofuranos-5-yl] -1,1 0-diaminodecane, N', N' ~ -di-[(5S~-deoxy-5 -(2w -hydroxy ethyl)- 3-0-benzyl- 1 ,2-0-isopropylidene-a-D-xylofuranos-5-yl]- 1,1 0-diaminodecane, N',N' " -di-[(SS/SR)-deoxy-5-(2 '-hydroxy
ethyl)- 3-0-benzyl- 1 ,2-0-isopropylidene-a-D-xylofuranos-5 -yl]- 1,10-

diaminodecane, N', N'2-di-II(5S~-deoxy-5-(2 '-hydroxy ethyl)- 3-0-methyl-i ,2-0-isopropylidene-a-D-xylofuranos-5 -yl]- 1,1 2-diaminododecane, N', N'2-di-[(SS/SR)-deoxy-5 -(2' -hydroxy ethyl)- 3-0-methyl- 1 ,2-0-isopropylidene-a-D-xvlnfuranos-5-yJ 1-1,1 2-diaminododecane, N', N '2-di-[(SS)-deoxy-5-(2 -hydroxy ethyl)-3-0-benzyl- 1 ,2-0-isopropylidene-ct-D-xylofuranos-5 -yl]- 1,12-

diaminododecane, N', N'2-di- [(5S/5R)-deoxy-5- (2'-hydroxyethyl)- 3-0-benzyl-1 ,2-0-isopropylidene-cL-D-xylofuranos-5-yl]- 1,1 2-diaminododecane, N, N -di-ESdeoxy-5-(2 '-hydroxyethyl)- 1 ,2-0-isopropylidene-3-0-methyl-cL-D-xylofuranos-5-yl]- 1 ,4-phenylenediureide, N, N -di-[5 -deoxy-5-(2 -hydroxyethyl)- 1,2-0-isopropylidene-3-0-methyl-a-D-xylofuranos-5-yl] -1 ,3-phenylenediureide, N, N -di-[5-deoxy-5 -(2' -hydroxyethyl)- 1 ,2-0-isopropylidene-3-0-benzyl-a-D-

xylofuranos-5-yl]- 1 ,3-phenylenediureide and N,N -di-[5-deoxy-5-(2 -hydroxyethyl)- 1 ,2-0-isopropylidene-3-0-benzyl-a-D-xylofuranos-5-yl] -1,4-phenylenediureide.

7. A process for the preparation of novel N',N~ -diglycosylated diaminoalcohols of formula 2, useful as antitubercular agent, substantially as herein described with reference to tl~e examples and drawing accompanying this specification.

Documents:

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998-del-2002-correspondence-others.pdf

998-del-2002-correspondence-po.pdf

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998-del-2002-drawings.pdf

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998-del-2002-form-2.pdf

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abstract.jpg


Patent Number 199829
Indian Patent Application Number 998/DEL/2002
PG Journal Number 40/2007
Publication Date 05-Oct-2007
Grant Date 28-Sep-2007
Date of Filing 30-Sep-2002
Name of Patentee COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH
Applicant Address RAFI MARG, NEW DELHI-110001, INDIA.
Inventors:
# Inventor's Name Inventor's Address
1 RAMA PATI TRIPATHI CENTRAL DRUG RESEARCH INSTITUTE, CHATTAR MANZIL PALACE, LUCKNOW-226001, U.P., INDIA.
2 VINOD KUMAR TIWARI CENTRAL DRUG RESEARCH INSTITUTE, CHATTAR MANZIL PALACE, LUCKNOW-226001, U.P., INDIA.
3 NEETU TEWARI CENTRAL DRUG RESEARCH INSTITUTE, CHATTAR MANZIL PALACE, LUCKNOW-226001, U.P., INDIA.
4 RANJANA SRIVASTVA CENTRAL DRUG RESEARCH INSTITUTE, CHATTAR MANZIL PALACE, LUCKNOW-226001, U.P., INDIA.
5 ANIL SRIVASTVA CENTRAL DRUG RESEARCH INSTITUTE, CHATTAR MANZIL PALACE, LUCKNOW-226001, U.P., INDIA.
6 VINITA CHATURVEDI CENTRAL DRUG RESEARCH INSTITUTE, CHATTAR MANZIL PALACE, LUCKNOW-226001, U.P., INDIA.
7 KISHORE KUMAR SRIVASTAVA CENTRAL DRUG RESEARCH INSTITUTE, CHATTAR MANZIL PALACE, LUCKNOW-226001, U.P., INDIA.
8 SUDHIR SINHA CENTRAL DRUG RESEARCH INSTITUTE, CHATTAR MANZIL PALACE, LUCKNOW-226001, U.P., INDIA.
9 BRAHM SHANKER SRIVASTAVA CENTRAL DRUG RESEARCH INSTITUTE, CHATTAR MANZIL PALACE, LUCKNOW-226001, U.P., INDIA.
PCT International Classification Number C07D 241/00
PCT International Application Number N/A
PCT International Filing date
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 NA