Indole compound
AssigneeTakeda Pharmaceutical Company Limited
InventorsTsuneo Yasuma, Osamu Ujikawa, Masahiro Itoh, Kazuko Aoki
Life of this patent
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Abstract
The purpose of the present invention is to provide a glucokinase activator useful as a pharmaceutical agent such as an agent for the prophylaxis or treatment of diabetes, obesity and the like. The present invention provides a glucokinase activator containing a compound represented by the formula (I): wherein R1 is a hydrogen atom or a halogen atom; R2 is a group represented by wherein each symbol is defined in the specification, or a salt thereof or a prodrug thereof.
Claims28
A compound represented by the formula (I):
- wherein
- R1 is a hydrogen atom or a halogen atom;
- R2 is a group represented by
- wherein
- A is CH or N;
- R4 and R5 are each independently an optionally substituted C1-6 alkyl group or an optionally substituted C3-10 cycloalkyl group, or R4 and R5 in combination form an optionally substituted ring wherein the ring should not be morpholine;
- and
- R6, R7, R21 and R22 are each independently a hydrogen atom, an optionally substituted hydrocarbon group, a cyano group or an acyl group, or R6 and R7 in combination form an optionally substituted ring;
- W is O or NR8 wherein R8 is a hydrogen atom, an optionally substituted C1-6 alkyl group or an optionally substituted C3-10 cycloalkyl group;
- R3 is an optionally substituted heterocyclic group or an optionally substituted C6-14 aryl group;
- and
- R9, R10 and R11 are each independently a hydrogen atom, a halogen atom, an optionally substituted C1-6 alkyl group or an optionally substituted C1-6 alkoxy group,
- provided that
- a compound wherein R21 is a hydrogen atom or a C1-6 alkoxy-carbonyl group, R22 is a hydrogen atom, and R6 and R7 are both hydrogen atoms, and
- a compound wherein R21 is a hydrogen atom or a C1-6 alkoxy-carbonyl group, R22 is a hydrogen atom, and R6 and R7 are both methyl groups
- are excluded,
- or a salt thereof.
N,N-dimethyl-2-{4-[(2-{7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}-1,3-thiazol-5-yl)methyl]piperazin-1-yl}acetamide;
- N-methyl-N-[2-(8-oxa-1-thia-3-azaspiro[4.5]dec-2-en-2-yl)-1H-indol-7-yl]thiophene-2-sulfonamide;
- N-[2-[4-(hydroxymethyl)-4,5-dihydro-1,3-thiazol-2-yl]-5-(2-methoxyethoxy)-1H-indol-7-yl]-N-methylpyridine-2-sulfonamide;
- 2-(2-{7-[methyl(pyridin-2-ylsulfonypamino]-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)acetamide;
- N-(difluoromethyl)-N-{2-[5-(morpholinomethyl)-4,5-dihydro-1,3-thiazol-2-yl]-1H-indol-7-yl}thiophene-2-sulfonamide;
- 2-(2-{7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}-1-thia-3,8-diazaspiro[4.5]dec-2-en-8-yl)acetamide;
- or
- N-[2-{5-[(1,1-dioxidothiomorpholino)methyl]-4,5-dihydro-1,3-thiazol-2-yl}-5-(2-methoxyethoxy)-1H-indol-7-yl]-N-methylpyridine-2-sulfonamide;
- or a salt thereof.
19-20. (canceled)
N,N-Dimethyl-2-{4-[(2-{7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}-1,3-thiazol-5-yl)methyl]piperazin-1-yl}acetamide or a salt thereof.
N-Methyl-N-[2-(8-oxa-1-thia-3-azaspiro[4.5]dec-2-en-2-yl)-1H-indol-7-yl]thiophene-2-sulfonamide or a salt thereof.
N-[2-[4-(Hydroxymethyl)-4,5-dihydro-1,3-thiazol-2-yl]-5-(2-methoxyethoxy)-1H-indol-7-yl]-N-methylpyridine-2-sulfonamide or a salt thereof.
(canceled)
2-(2-{7-[Methyl(pyridin-2-ylsulfonypamino]-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)acetamide or a salt thereof.
N-(Difluoromethyl)-N-{2-[5-(morpholinomethyl)-4,5-dihydro-1,3-thiazol-2-yl]-1H-indol-7-yl}thiophene-2-sulfonamide or a salt thereof.
27-28. (canceled)
2-(2-{7-[Methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}-1-thia-3,8-diazaspiro[4.5]dec-2-en-8-yl)acetamide or a salt thereof.
N-[2-{5-[(1,1-Dioxidothiomorpholino)methyl]-4,5-dihydro-1,3-thiazol-2-yl}-5-(2-methoxyethoxy)-1H-indol-7-yl]-N-methylpyridine-2-sulfonamide or a salt thereof.
Dependencies are inferred from the claim text.