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US 6,388,071 B2Granted
Alkynyl phenyl heteroaromatic glucokinase activators
AssigneeHoffmann-La Roche Inc.
InventorPaige Erin Mahaney
Life of this patent
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Abstract
Para-alkynyl phenyl heteroaromatic amides which are active as glucokinase activators to increase insulin secretion which makes them useful for treating type II diabetes.
Claims25
A compound of the formula:
- wherein R is hydrogen, lower alkyl, hydroxy lower alkyl, lower alkoxy lower alkyl,
- an unsubstituted or hydroxy substituted cycloalkyl ring containing 5 or 6 carbon atoms, a five- or six-membered saturated heterocyclic ring which contains from 1 to 3 hetero ring atoms selected from the group consisting of sulfur, oxygen or nitrogen, or an unsubstituted five- or six-membered heteroaromatic ring, connected by a ring carbon atom, which contains from 1 to 3 heteroatoms in the ring selected from the group consisting of sulfur, nitrogen and oxygen;
- R3 is cycloalkyl having 3 to 7 carbon atoms;
- R4 is an unsubstituted or mono-substituted five- or six-membered heteroaromatic ring, connected by a ring carbon atom to the amine group shown, which five- or six-membered heteroaromatic ring contains from 1 to 3 heteroatoms selected from sulfur, oxygen or nitrogen, with one heteroatom being nitrogen adjacent to the connecting ring carbon atom;
- said mono-substituted heteroaromatic ring 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,
- —(CH2)m—OR6,
- —(CH2)m—NHR6;
- n is the integer 0, 1 or 2;
- m is 0, 1, 2, 3 or 4;
- R1, R2, R6, R7 and R8 are independently hydrogen or lower alkyl and * designates
- the assymetric carbon atom center;
- or a pharmaceutically acceptable salt thereof.
9 more elements
Dependencies are inferred from the claim text.