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US 6,610,846 B1Granted
Heteroaromatic glucokinase activators
AssigneeHoffman-La Roche Inc.
InventorsFred Thomas Bizzarro, Wendy Lea Corbett, Joseph Francis Grippo, Nancy-Ellen Haynes, George William Holland, Robert Francis Kester, Paige Erin Mahaney, Ramakanth Sarabu
Life of this patent
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Abstract
2,3-Di-substituted N-heteroaromatic propionamides with said substitution at the 3-position being a substituted phenyl group and at the 2-position being a methyl cycloalkyl ring, said propionamides being glucokinase activators which increase insulin secretion in the treatment of type II diabetes.
Claims28
A compound selected from the group consisting of amides of the formula:
- wherein,
- the * indicates an asymmetric carbon atom,
- R1 and R2 are independently hydrogen, halo, amino, hydroxyamino, cyano, nitro, lower alkyl, —OR5, —C(O)OR6, perfluoro-lower alkyl, lower alkyl thio, perfluoro-lower alkyl thio, lower alkyl sulfonyl, lower alkoxy lower alkyl sulfonyl, perfluoro-lower alkyl sulfonyl, lower alkyl sulfinyl, or sulfonamido;
- R3 is cycloalkyl having from 3 to 7 carbon atoms or lower alkyl having from 2 to 4 carbon atoms;
- R4 is an unsubstituted or mono-substituted triazine, pyrazine or pyridazine connected by a ring carbon atom to the amide group shown, with one heteroatom being nitrogen which is adjacent to the connecting ring carbon atom;
- said mono-substituted triazine, pyrazine or pyridazine being monosubstituted at a position on a ring carbon atom other than adjacent to said connecting carbon atom with a substituent selected from the group consisting of lower alkyl, halo, nitro, cyano, perfluoro-lower alkyl, oxo, —(CH2)n—OR7, —(CH2)n—C(O)—OR7, —(CH2)n—C(O)—NH—R7, —C(O)C(O)—OR7, or —(CH2)n—NHR7;
- n is 0, 1, 2, 3 or 4;
- R5 is hydrogen, lower alkyl, or perfluoro-lower alkyl;
- R6 is lower alkyl;
- and
- R7 is hydrogen or lower alkyl;
- or a pharmaceutically acceptable salt thereof.
9 more elements
Dependencies are inferred from the claim text.