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Generated: July 27, 2017

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Title:Substituted indazole-O-glucosides
Abstract: Substituted indazole-O-glucosides, compositions containing them, and methods of using them, for example for the treatment of diabetes and Syndrome X are disclosed.
Inventor(s): Patel; Mona (Belle Mead, NJ), Rybczynski; Philip J. (Branchburg, NJ), Urbanski; Maud (Flemington, NJ), Zhang; Xiaoyan (Belle Mead, NJ)
Assignee: Janssen Pharmaceutica, N.V. (Beerse, BE)
Filing Date:Jul 30, 2004
Application Number:10/903,034
Claims:1. A compound of formula(II): ##STR00032## wherein R.sup.1 is H or C.sub.1-4 alkyl; R.sup.2 is H, F, Cl, methoxy, or C.sub.1-3 alkyl; Q is --(CH.sub.2).sub.n-- where n=0, 1, or 2; or, where R.sup.2 is H, F, Cl, or methoxy, then Q can also be selected from --CH.sub.2--S--; Z is substituted or unsubstituted, and is selected from C.sub.3-7 cycloalkyl, phenyl, benzhydryl, 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 each fused heterobicyclyl has between 1 and 4 heteroatoms independently selected from. N, O, and S; P=H or acetyl; or a pharmaceutically acceptable salt thereof.

2. A compound of claim 1, wherein R.sup.1 is H.

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 or 2.

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, C.sub.1-4 alkyl, C.sub.3-6 cycloalkyl, halo, hydroxy, cyano, amino, C.sub.1-4 alkylthio, C.sub.1-4 aminoalkyl, mono- and di(C.sub.1-4 alkyl)amino, phenyl, 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, C.sub.1-4 alkylthio, phenoxy, --CONR.sup.aR.sup.b, --NHSO.sub.2R.sup.a, and --SO.sub.2NR.sup.aR.sup.b where each of R.sup.a and R.sup.b is independently selected from H and C.sub.1-4 alkyl.

6. A compound of claim 1, wherein Z is phenyl, cyclopentyl, cyclohexyl, 4-substituted cyclohexyl, 2- or 3-substituted cyclopentyl, 4-substituted phenyl, 3,4-disubstituted phenyl, substituted thiophenyl, thiophenyl, biaryl, benzofuranyl, dihydrobenzofuranyl, 4-substituted pyridyl, benzo[b]thienyl, benzothiophenyl, indanyl, naphthyl, 5,6,7,8-tetrahydronapthyl, 1,2,3,4-tetrahydronaphthyl, or benzo[1,4] dioxan.

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

8. A compound of claim 1, wherein Z is biphenyl, 4-ethylphenyl, (4-propyl)phenyl, 4-methoxyphenyl, 4-ethoxyphenyl, 4-methylthiophenyl, benzofuran-5-yl, dihydrobenzofuran-5-yl, naphthyl, or dihydrobenzofuran-6-yl, or (5-ethylthio)phenyl.

9. A compound of claim 1 wherein R.sup.1 is H; and R.sup.2 is H, methyl, ethyl, propyl, or isopropyl.

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

11. A compound of claim 10, wherein R.sup.1 is methyl.

12. A compound of claim 2, wherein R.sup.2 is H, methyl, or ethyl; wherein Q is --(CH.sub.2).sub.n-- and n is 1 or 2; Z is phenyl, cyclopentyl, cyclohexyl, 4-substituted cyclohexyl, 2- or 3-substituted cyclopentyl, 4-substituted phenyl, 3,4-disubstituted phenyl, substituted thiophene, thiophenyl, biaryl, benzofuranyl, dihydrobenzofuranyl, 4-substituted pyridyl, benzo[b]thienyl, benzothiophenyl, indanyl, naphthyl, 5,6,7,8-tetrahydronapthyl, 1,2,3,4-tetrahydronaphthyl, or benzo[1,4] dioxan; and wherein Z is unsubstituted or substituted with between 1 and 2 substituents independently selected from methoxy, ethoxy, fluoro, chloro, methyl, ethyl, propyl, isopropyl, cyclopropyl, and phenyl.

13. A compound of claim 1, wherein R.sup.2 is H, methyl, or ethyl; wherein Q is --(CH.sub.2).sub.n-- and n is 1 or 2; and Z is biphenyl, 4-ethylphenyl, (4-propyl)phenyl, 4-methoxyphenyl, 4-ethoxyphenyl, 4-methylthiophenyl, benzofuran-5-yl, dihydrobenzofuran-5-yl, naphthyl, or dihydrobenzofuran-6-yl, or (5-ethylthio)phenyl.

14. A compound of claim 1, selected from 2-{3-[2-(2,3-Dihydro-benzofuran-5-yl)-ethyl]-6-methyl-1H-indazol-4-yloxy}- -.beta.-D-glucopyranoside; 2-[3-(2-Benzofuran-5-yl-ethyl)-6-methyl-1H-indazol-4-yloxy]-.beta.-D-gluc- opyranoside; 2-{3-[2-(2,3-Dihydro-benzofuran-5-yl)-ethyl]-1,6-dimethyl-1H-indazol-4-yl- oxy}-.beta.-D-glucopyranoside; 2-{3-[2-(2,3-Dihydro-benzofuran-5-yl)-ethyl]-6-ethyl-1H-indazol-4-yloxy}-- .beta.-D-glucopyranoside and 2-[3-(4-Methoxy-benzyl)-6-methyl-1H-indazol-4-yloxy]-.beta.-D-glucopyrano- side.

15. A compound of claim 1, selected from 2-[3-(2-Benzofuran-5-yl-ethyl)-1H-indazol-4-yloxy]-.beta.-D-glucopyranosi- de; 2-{3-[2-(6-Methoxy-naphthalen-2-yl)-ethyl]-6-methyl-1H-indazol-4-yloxy- }-.beta.-D-glucopyranoside; 2-{3-[2-(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-ethyl]-6-methyl-1H-indazol4-y- loxy}-.beta.-D-glucopyranoside; 2-{3-[2-(4-Ethoxy-phenyl)-ethyl]-6-methyl-1H-indazol-4-yloxy}-.beta.-D-gl- ucopyranoside; 2-{6-Methyl-3-[2-(5,6,7,8-tetrahydro-naphthalen-2-yl)-ethyl]-1H-indazol-4- -yloxy}-.beta.-D-glucopyranoside; 2-[6-Methyl-3-(2-naphthalen-2-yl-ethyl)-1H-indazol-4-yloxy]-.beta.-D-gluc- opyranoside; 2-{3-[2-(4-Methoxy-phenyl)-ethyl]-6-methyl-1H-indazol-4-yloxy}-.beta.-D-g- lucopyranoside; 2-{3-[2-(6-Methoxy-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethyl]-6-methyl-1H- -indazol-4-yloxy}-.beta.-D-glucopyranoside and 2-[3-(2-Benzofuran-5-yl-ethyl)-6-methyl-1H-indazol-4-yloxy]-6-O-acetyl-.b- eta.-D-glucopyranoside.

16. A compound of claim 1, selected from 2-{3-[2-(6-Methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-ethyl]-6-methyl-1H- -indazol-4-yloxy}-.beta.-D-glucopyranoside; 2-{3-[2-(4-Chloro-phenyl)-ethyl]-6-methyl-1H-indazol-4-yloxy}-.beta.-D-gl- ucopyranoside: 2-[3-(4-Methoxy-phenylsulfanylmethyl)-1H-indazol-4-yloxy]-.beta.-D-glucop- yranoside; 2-[3-(2-Cyclohexyl-ethyl)-6-methyl-1H-indazol-4-yloxy]-.beta.-D- -glucopyranoside; 2-[3-(2,3-Dihydro-benzofuran-5-ylmethyl)-6-methyl-1H-indazol-4-yloxy]-.be- ta.-D-glucopyranoside; 2-{3-[2-(4-Trifluoromethyl-phenyl)-ethyl]-6-methyl-1H-indazol-4-yloxy}-.b- eta.-D-glucopyranoside; 2-{3-[2-(4-Methanesulfonylamino-phenyl)-ethyl]-6-methyl-1H-indazol-4-ylox- y}-.beta.-D-glucopyranoside and 2-{3-[2-(2,3-Dihydro-benzofuran-5-yl)-ethyl]-6-methyl-1H-indazol-4-yloxy}- -6-O-acetyl-.beta.-D-glucopyranoside.

17. A compound of claim 1, selected from 2-[3-(4-Ethyl-benzyl)-6-methyl-1H-indazol-4-yloxy]-.beta.-D-glucopyranosi- de; 2-[6-Methyl-3-(4-propyl-benzyl)-1H-indazol-4-yloxy]-.beta.-D-glucopyra- noside; 2-[3-(4-Methylsulfanyl-benzyl)-6-methyl-1H-indazol-4-yloxy]-.beta.- -D-glucopyranoside; 2-[3-(4-Biphenyl)-6-methyl-1H-indazol-4-yloxy]-.beta.-D-glucopyranoside; 2-[3-(4-Cyclopropyl-benzyl)-6-methyl-1H-indazol-4-yloxy]-.beta.-D-glucopy- ranoside and 2-[3-(5-Ethylthiophen-2-ylmethyl)-6-methyl-1H-indazol-4-yloxy]-.beta.-D-g- lucopyranoside.

18. A compound of claim 1, selected from 2-{3-[2-(2,3-Dihydro-benzofuran-5-yl)-ethyl]-6-methyl-1H-indazol-4-yloxy} .beta.-D-glucopyranoside; 2-[3-(2-Benzofuran-5-yl-ethyl)-6-methyl-1H-indazol-4-yloxy]-.beta.-D-gluc- opyranoside; 2-[3-(4-Ethyl-benzyl)-6-methyl-1H-indazol-4-yloxy]-.beta.-D-glucopyranosi- de; and 2-[3-(5-Ethylthiophen-2-ylmethyl)-6-methyl-1H-indazol-4-yloxy]-.be- ta.-D-glucopyranoside.

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.
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