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Details for Patent: 7,094,764

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Details for Patent: 7,094,764

Title:Substituted benzimidazole-, Benztriazole-, and benzimidazolone-O-glucosides
Abstract: This invention relates to to substituted benzimidazole-O-glucosides, benztriazole-O-glucosides, and benzimidazolone-O-glucosides, compositions containing them, and methods of using them, for example, for the treatment or prophylaxis of diabetes and Syndrome X.
Inventor(s): Urbanski; Maud (Flemington, NJ)
Assignee: Janssen Pharmaceutica N.V. (Beerse, BE)
Filing Date:Jul 30, 2004
Application Number:10/903,234
Claims:1. A compound of formula (III): ##STR00019## wherein: X is CH, N, or C.dbd.O; R.sub.1 is H or absent; R.sub.2 is H, F, Cl, OCH.sub.3, OCH.sub.2CH.sub.3, or C.sub.1-4 alkyl, CF.sub.3, SCH.sub.3, substituted or unsubstituted phenyl or NR.sub.3R.sub.4; R.sub.3 and R.sub.4 are H, C.sub.1-6 alkyl, or taken together with the nitrogen atom to which they are both attached form a 5 6 membered heterocyclyl with optionally 1 2 additional heteroatoms independently selected from O, S, or N; Q is --(CH.sub.2).sub.n-- where n is 1 or 2; P is H, C.sub.1-7 acyl, or (C.sub.1-6 alkoxy)carbonyl; and Z is substituted or unsubstituted, and is selected from C.sub.3-7 cycloalkyl, phenyl, 5- or 6-membered heteroaryl having 1 or 2 heteroatoms independently selected from N, O, and S, a biaryl, and a 9- or 10-membered fused bicyclyl or 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.sup.1 is H or absent.

3. A compound of claim 1, wherein R.sup.2 is H, methyl, or ethyl.

4. A compound of claim 1, wherein Q is --(CH.sub.2).sub.n-- and n is 1.

5. 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 alkyl)amino, phenyl, C.sub.1-4 alkylaminosulfonyl (SO.sub.2NHR), amino-(alkylsulfonyl) (--NHSO.sub.2R--), C.sub.1-4 dialkylaminosulfinyl (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 substituents 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.

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

7. A compound of claim 4, 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.

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

9. A compound of claim 1, wherein R.sub.1 is absent; X is CH and R.sub.2 is H, methyl, ethyl, or methoxy.

10. A compound of claim 1, wherein Q is --(CH.sub.2).sub.n--, n is 1 or 2; and R.sub.2 is H, methyl, or ethyl.

11. A compound of claim 10, wherein R.sub.1 is absent.

12. A compound of claim 1, wherein R.sub.1 is absent; Q is --(CH.sub.2).sub.n--; n is 1 or 2; and R.sub.2 is H, methyl, or ethyl; and Z is 4-substituted phenyl, 3,4-disubstituted phenyl, benzhydryl, substituted or unsubstituted thiophene, biaryl, benzofuranyl, hydrobenzofuranyl, dihydrobenzofuranyl, 4-substituted pyridyl, benzo[b]thienyl, chromanyl, benzothiophenyl, indenyl, indanyl, naphthyl, or 2,3-dihydro-benzo[1,4]dioxanyl.

13. A compound of claim 1, wherein Z is biphenyl, 4-(3-pyridyl) phenyl, 4-(2-thienyl)phenyl, 4-(1H-imidazole-1-yl)-phenyl, 4-(1H-pyrazol-1-yl)-phenyl, (4-ethyl)phenyl, (4-propyl)phenyl, (4-methoxyphenyl), 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.

14. A compound of claim 1, selected from 2-{3-[2-(2,3-Dihydro-benzofuran-5-yl)-ethyl]-3H-benzoimidazol-4-yloxy}-.b- eta.-D glucopyranoside; 2-[3-(4-Ethyl-benzyl)-3H-benzoimidazol-4-yloxy]-.beta.-D-glucopyranoside and 2-[3-(4-Ethyl-benzyl)-3H-benzotriazol-4-yloxy]-.beta.-D-glucopyranosi- de.

15. A compound of claim 1, selected from 2-[3-(4-Ethyl-benzyl) -6-methyl-3H-benzoimidazol-4-yloxy]-.beta.-D-glucopyranoside; 2-{3-[2-(4-Methoxyphenyl) -ethyl]-3H-benzoimidazol-4-yloxy}-.beta.-D-glucopyranoside; 2-{3-[2-(4-methoxy-phenyl) -ethyl]-3H-benzotriazol-4-yloxy}-.beta.-D-glucopyranoside; 2-[3-(2-Naphthalen-2-yl-ethyl) -3H-benzoimidazol-4-yloxy]-.beta.-D-glucopyranoside and 2-[3-(4-Ethyl-benzyl) -1,3-dihydro-benzoimidazol-2-one-4-yloxy]-.beta.-D-glucopyranoside.

16. A compound of claim 1, selected from 2-[3-(2-Naphthalen-2-yl-ethyl) -1,3-dihydro-benzoimidazol-2-one-4-yloxy]-.beta.-D-glucopyranoside and 2-[3-(2-(4-Methoxyphenyl) -ethyl)-1,3-dihydro-benzoimidazol-2-one-4-yloxy]-.beta.-D glucopyranoside.

17. A compound of claim 1, selected from 2-[3-(5-Ethyl-thiophen-2-ylmethyl) -3H-benzoimidazol-4-yloxy]-.beta.-D-glucopyranoside; 2-[3-(4-Ethoxy-benzyl)-3H -benzoimidazol-4-yloxy]-.beta.-D-glucopyranoside; 2-[3-(4-Ethoxy-benzyl)-3H-benzotriazol-4-yloxy]-.beta.-D-glucopyranoside; 2-{3-[2-(2,3-Dihydro-benzofuran-5-yl)-ethyl]-6-methyl-3H-benzoimidazol-4-- yloxy}-.beta.-D-glucopyranoside; 2-[3-(4-Thiophen-3-yl-benzyl) -3H-benzoimidazol-4-yloxy]-.beta.-D-glucopyranoside; 2-[3-(4-Pyrazol-1-yl-benzyl) -3H-benzoimidazol-4-yloxy]-.beta.-D-glucopyranoside; 2-[3-(4-Pyridin-3-yl-benzyl) -3H-benzoimidazol-4-yloxy]-.beta.-D-glucopyranoside; 2-[3-(4-Pyrrol-1-yl-benzyl) -3H-benzoimidazol-4-yloxy]-.beta.-D-glucopyranoside; 2-[3-(4-Imidazol-1-yl-benzyl)-3H-benzoimidazol -4-yloxy]-.beta.-D-glucopyranoside; 2-(3-Biphenyl-4-ylmethyl-3H-benzoimidazol -4-yloxy)-.beta.-D-glucopyranoside; 2-[3-(4-Ethyl-benzyl)-6-methoxy-3H-benzoimidazol -4-yloxy]-.beta.-D-glucopyranoside; 2-[3-(4-Ethyl-benzyl)-6-trifluoromethyl-3H -benzoimidazol-4-yloxy]-.beta.-D-glucopyranoside; 2-[3-(4-Ethyl-benzyl)-3H-benzoimidazol -4-yloxy]-6-O-ethoxycarbonyl-.beta.-D-glucopyranoside; 2-[3-(4-Ethyl-benzyl) -3H-benzotriazol-4-yloxy]-6-O-ethoxycarbonyl-.beta.-D-glucopyranoside and 2-[3-(4-Ethyl-benzyl) -6-methyl-3H-benzotriazol-4-yloxy]-.beta.-D-glucopyranoside.

18. A compound of claim 1, selected from 2-[3-(4-Ethyl-benzyl)-3H-benzoimidazol -4-yloxy]-.beta.-D-glucopyranoside; 2-{3-[2-(2,3-Dihydro-benzofuran-5-yl)-ethyl]-3H-benzoimidazol-4-yloxy}-.b- eta.-D glucopyranoside; 2-[3-(4-Ethyl-benzyl)-3H-benzotriazol -4-yloxy]-.beta.-D-glucopyranoside; 2-[3-(4-Ethyl-benzyl)-6-methyl-3H-benzoimidazol -4-yloxy]-.beta.-D-glucopyranoside; 2-{3-[2-(4-methoxy-phenyl)-ethyl]-3H-benzotriazol -4-yloxy}-.beta.-D-glucopyranoside; 2-[3-(5-Ethyl-thiophen-2-ylmethyl)-3H-benzoimidazol -4-yloxy]-.beta.-D-glucopyranoside; 2-{3-[2-(2,3-Dihydro-benzofuran-5-yl)-ethyl]-6-methyl-3H-benzoimidazol-4-- yloxy}-.beta.-D-glucopyranoside; 2-[3-(4-Thiophen-3-yl-benzyl) -3H-benzoimidazol-4-yloxy]-.beta.-D-glucopyranoside; 2-[3-(4-Pyrrol-1-yl-benzyl) -3H-benzoimidazol-4-yloxy]-.beta.-D-glucopyranoside; 2-{3-[2-(2,3-Dihydro-benzofuran -5-yl)-ethyl]-6-methyl-3H-benzoimidazol-4-yloxy}-.beta.-D-glucopyranoside- ; 2-{3-[2-(2,3-Dihydro-benzofuran-5-yl)-ethyl]-6-methyl-3H-benzotriazol-4-- yloxy}-.beta.-D-glucopyranoside; 2-{3-[2-(2,3-Dihydro-benzofuran-5-yl)-ethyl]-3H-benzotriazol-4-yloxy}-.be- ta.-D-glucopyranoside and 2-[3-(4-Ethyl-benzyl)-6-methyl-3H-benzotriazol-4-yloxy]-.beta.-D-glucopyr- anoside.

19. A pharmaceutical composition, comprising a compound of claim 1, 5, 6, 11, 12, 14, 15, 16, 17, or 18 and a pharmaceutically acceptable carrier.

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