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Details for Patent: 7,094,763

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Details for Patent: 7,094,763

Title:Substituted fused heterocyclic C-glycosides
Abstract: This invention relates to substituted fused heterocyclic C-glycosides, compositions containing them, and methods of using them, for example, for the treatment or prophylaxis of diabetes and Syndrome X.
Inventor(s): Rybczynski; Philip (Branchburg, NJ), Urbanski; Maud (Flemington, NJ), Zhang; Xiaoyan (Belle Mead, NJ)
Assignee: Janssen Pharaceutica, N.V. (BE)
Filing Date:Jul 30, 2004
Application Number:10/903,136
Claims:1. A compound of formula IV: ##STR00017## wherein: one of the dashed lines between NR.sub.1 and X or between X and Y is present and if present such dashed lines represent a double bond, or alternatively both dashed lines are absent; two of V, M, and W are H and the third is ##STR00018## R.sub.1 is H, or C.sub.1-4 alkyl; or, where the dashed line between NR.sup.1 and X is present, R.sub.1 is absent; X is N, C.dbd.O, CH, or C--Q--Z; Y is N--Q--Z or C--Q--Z, where X is N, C.dbd.O, or CH; Y is CH, where X is C--Q--Z; Q=--(CH.sub.2).sub.n-- where n=1 or 2; P=H, C.sub.1-7 acyl, or C.sub.1-6 alkoxycarbonyl; Z is substituted or unsubstituted, and is selected from C.sub.3-7 cycloalkyl, phenyl, a 5- or 6- membered heteroaryl having 1 or 2 heteroatoms independently selected from N, O, and S, a biaryl, a 9- or 10-membered fused bicyclyl, and a fused heterobicyclyl, wherein said fused heterobicyclyl has between 1 and 4 heteroatoms independently selected from N, O, and S; or a pharmaceutically acceptable salt, thereof.

2. A compound of claim 1, wherein R.sub.1 is H or absent.

3. A compound of claim 1, wherein Z is independently substituted with between 1 and 3 substituents independently selected from C.sub.1-4 alkoxy, phenoxy, C.sub.1-4 alkyl, C.sub.3-6 cycloalkyl, halo, hydroxy, cyano, amino, C.sub.1-4 alkylthio, C.sub.1-4 alkylsulfonyl, C.sub.1-4 alkylsulfinyl, C.sub.1-4 aminoalkyl, mono and di C.sub.1-4 alkylamino, phenyl, C.sub.1-4 alkylaminosulfonyl (SO.sub.2NHR), amino(C.sub.1-4 alkylsulfonyl) (NHSO.sub.2R), di C.sub.1-4 alkylaminosulfinyl (SONHRR), C.sub.1-4 alkylamido (NHCOR), C.sub.1-4 alkylcarbamido (CONHR), 5 6 membered heterocyclyl containing between 1 and 3 heteroatoms independently selected from N, S, and O; and wherein the substituent(s) on Z can be further independently substituted with between 1 and 3 substitutents independently selected from C.sub.1-4 alkoxy, C.sub.1-4 alkyl, halo, hydroxy, cyano, amino, mono or di C.sub.1-4 alkyl amino and C.sub.1-4 alkylthio.

4. A compound of claim 1, wherein Z is 4-substituted phenyl, 3,4-disubstituted phenyl, benzhydryl, substituted or unsubstituted thiophenyl, biaryl, benzofuranyl, hydrobenzofuranyl, dihydrobenzofuranyl 4-substituted pyridyl, benzo[b]thienyl, chromanyl, benzothiophenyl, indanyl, naphthyl, and 2,3-dihydro-benzo[1,4] dioxan.

5. A Compound of claim 3, wherein Z is unsubstituted or substituted with between 1 and 2 substituents independently selected from methoxy, ethoxy, fluoro, chloro, methyl, ethyl, propyl, butyl and isopropyl.

6. A compound of claim 1, wherein Z is biphenyl, 4-(3-pyridyl)phenyl, 4-(2-thienyl)phenyl, 4-(1H-pyrazol-1-yl)-phenyl, (4ethyl)phenyl, (4-propyl)phenyl, (4-methoxy)phenyl, dihydrobenzofuran-5-yl, or dihydrobenzofuran-6-yl.

7. A compound of claim 1 wherein R.sub.1 is H.

8. A compound of claim 1, wherein n is 1.

9. A compound of claim 8, wherein R.sub.1 is H or absent.

10. A compound of claim 1, wherein Z is biphenyl, 4-(3-pyridyl)phenyl, 4-(2-thienyl)phenyl, 4-(1H-pyrazol-1-yl)-phenyl, (4-ethyl)phenyl, (4-propyl)phenyl), (4-methoxy)phenyl, dihydrobenzofuran-5-yl, or dihydrobenzofuran-6-yl; and Z is unsubstituted or substituted with between 1 and 2 substituents independently selected from methoxy, ethoxy, fluoro, chloro, methyl, ethyl, propyl, butyl and isopropyl.

11. A compound of claim 10, wherein n is 1.

12. A compound of claim 10, wherein R is H.

13. A compound of claim 1, wherein M and V are H.

14. A compound of claim 1, wherein M and W are H.

15. A compound of claim 1, wherein X is CH and Y is C--Q--Z.

16. A compound of claim 1, wherein X is C--Q--Z and Y is CH.

17. A compound of claim 15, wherein R.sub.1 is H or absent, and n=1.

18. A compound of claim 1, selected from 3-(4-Ethylbenzyl)-5(.beta.-D-glucopyranosyl)-1H-indole; 5-(.beta.-D-Glucopyranosyl)-3-(4-methoxybenzyl)-1H-indole; 5-(.beta.-D-Glucopyranosyl)-3-[2-(4-methoxyphenyl)-ethyl]-1H-indole and 3-(4-Ethylbenzyl)-4-(.beta.-D-glucopyranosyl)-1H-indole.

19. A compound of claim 1, selected from 2-(4-Ethylbenzyl)-4-(.beta.-D-glucopyranosyl)-1H-indole; 3-[2-(2,3-Dihydro-benzofuran-5-yl)ethyl]-5-(.beta.-D-glucopyranosyl)-1H-i- ndole; 5-(.beta.-D-Glucopyranosyl)-3-(5-methyl-2-thienyl)-1H-indole; 3-(4-Ethylbenzyl)-4-(.beta.-D-glucopyranosyl)-3H-benzimidazole; 3-(4-Ethylbenzyl)-4-(.beta.-D-glucopyranosyl)-1,3-dihydro-benzoimidazol-2- -one and 3-(4-Ethylbenzyl)-4-(.beta.-D-glucopyranosyl)-3H-benzotriazole.

20. A compound of claim 1, selected from 3-(4-Ethylbenzyl)-5-(.beta.-D-glucopyranosyl)-1H-indole; 2-(4-Ethylbenzyl)-4-(.beta.-D-glucopyranosyl)-1H-indole; 5-(.beta.-D-Glucopyranosyl)-3-(5-methyl-2-thienyl)-1H-indole;3-(4-Ethylbe- nzyl)-4-(.beta.-D-glucopyranosyl)-3H-benzimidazole and 3-(4-Ethylbenzyl)-4-(.beta.-D-glucopyranosyl)-3H-benzotriazole.

21. A pharmaceutical composition, comprising a compound of claim 1, 5, 6, 11, 12, 13, 15, 16, 17, 18, 19 or 20 and a pharmaceutically acceptable carrier.

22. A pharmaceutical composition, comprising a compound of claim 14 and a pharmaceutically acceptable carrier.
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