US2003060625A1PendingUtilityA1
Para-amine substituted phenylamide glucokinase activators
Priority: May 8, 2000Filed: Sep 26, 2002Published: Mar 27, 2003
Est. expiryMay 8, 2020(expired)· nominal 20-yr term from priority
C07D 213/82C07D 417/12C07D 277/46
46
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Claims
Abstract
Para-alkyl, aryl, cycloheteroalkyl or heteroaryl [carbonyl or sulfonyl] amino substituted phenyl amides active as glucokinase activators to increase insulin secretion which makes them useful for treating type II diabetes.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1 . An amide selected from the group consisting of a compound of the formula
wherein X is
wherein R is perfluoro-lower alkyl, lower alkyl,
lower alkoxycarbonyl, a heteroaromatic ring, connected by a ring carbon atom, containing from 5 to 6 ring members with from 1 to 3 heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen, unsubstituted aryl containing 6 or 10 ring carbon atoms, a nitro or a lower alkyl substituted aryl which aryl contains 6 or 10 ring carbon atoms or a saturated 5- or 6-membered cycloheteroalkyl ring, connected by a ring carbon atom, containing from 1 to 2 heteroatoms selected from the group consisting of oxygen, nitrogen, sulfur or cycloalkyl having 5 or 6 carbon atoms; R 1 is cycloalkyl having 5 or 6 carbon atoms; R 2 is a five- or six-membered heteroaromatic ring connected by a ring carbon atom to the amide group to the remainder of the compound, which heteroaromatic ring contains from 1 to 3 heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen with a first heteroatom being nitrogen which is adjacent to the connecting ring carbon atom, said heteroaromatic ring being unsubstituted or 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, or
n and y are independently an integer from 1 to 4; R 4 , R 5 and R 7 are independently hydrogen or lower alkyl; and * denotes the asymmetric carbon atom and a pharmaceutically acceptable salt thereof.
2 . The amide of claim 1 wherein said compound is
wherein R, R 1 , R 2 and y are as above.
3 . The amide of claim 2 wherein R 1 is cyclopentyl.
4 . The amide of claim 4 wherein R 2 is a substituted or unsubstituted five-membered heteroaromatic ring.
5 . The amide of claim 4 wherein R is aryl substituted with a nitro group.
6 . The amide of claim 5 wherein said compound is N-{4-[2-cyclopentyl-1-(thiazol-2-ylcarbamoyl)-ethyl]-phenyl}-4-nitro-benzamide.
7 . The amide of claim 4 wherein R is unsubstituted aryl.
8 . The amide of claim 7 wherein said compound is N-{4-[2-cyclopentyl-1-(thiazol-2-ylcarbamoyl)-ethyl]-phenyl}-benzamide.
9 . The amide of claim 4 wherein R is said heteroaromatic ring.
10 . The amide of claim 9 wherein said compound is 3-cyclopentyl-N-thiazol-2-yl-2-[4-(2-thiophen-2-yl-acetylamino)-phenyl]-propionamide.
11 . The amide of claim 9 wherein said compound is N-{4-[2-cyclopentyl-1-(thiazol-2-ylcarbamoyl)-ethyl]-phenyl}-isonicotinamide.
12 . The amide of claim 9 wherein said compound is 2-(3-cyclopentyl-2-{4-[(pyridine-3-carbonyl)-amino]-phenyl}-propionylamino)-thiazole-4-carboxylic acid ethyl ester.
13 . The amide of claim 9 wherein said compound is N-{4-[2-cyclopentyl-1-(thiazol-2-ylcarbamoyl)-ethyl]-phenyl}-nicotinamide.
14 . The amide of claim 9 wherein said compound is [2-(3-cyclopentyl-2-{4-[(pyridine-3-carbonyl)-amino]-phenyl}-propionylamino)-thiazol-4-yl]-acetic acid ethyl ester.
15 . The amide of claim 3 wherein R 2 is a substituted or unsubstituted 6-membered heteroaromatic ring.
16 . The amide of claim 15 wherein R is unsubstituted aryl or heteroaromatic ring.
17 . The amide of claim 16 wherein said compound is N-{4-[2-cyclopentyl-1-(pyridin-2-ylcarbamoyl)-ethyl]-phenyl}-nicotinamide.
18 . The amide of claim 16 wherein said compound is 6-(3-cyclopentyl-2-{4-[(pyridine-3-carbonyl)-amino]-phenyl}-propionylamino)-nicotinic acid methyl ester.
19 . The amide of claim 16 wherein said compound is 6-(3-cyclopentyl-2-{4-[(pyridine-3-carbonyl)-amino]-phenyl}-propionylamino)-nicotinic acid.
20 . The amide of claim 4 wherein R is lower alkoxy carbonyl.
21 . The amide of claim 20 wherein said compound is N-{4-[2-cyclopentyl-1-(thiazol-2-ylcarbamoyl)-ethyl]-phenyl}-oxalamic acid methyl ester.
22 . The amide of claim 20 wherein said compound is acetic acid {4-[2-cyclopentyl-1-(thiazol-2-ylcarbamoyl)-ethyl]-phenylcarbamoyl}-methyl ester.
23 . The amide of claim 1 wherein said compound is
wherein R, R 1 , R 2 and y are as above.
24 . The compound of claim 23 wherein R 1 is cyclopentyl.
25 . The amide of claim 24 wherein R 2 is a 5-membered heterocyclic ring.
26 . The amide of claim 25 wherein R 2 is thiazolyl.
27 . The amide of claim 26 wherein R is lower alkyl or perfluorolower alkyl.
28 . The amide of claim 27 wherein said compound is 3-cyclopentyl-2-(4-methanesulfonylamino-phenyl)-N-thiazol-2-yl-propionamide.
29 . The amide of claim 27 wherein said compound is 3-cyclopentyl-N-thiazol-2-yl-2-(4-trifluoromethanesulfonylamino-phenyl)-propionamide.
30 . The amide of claim 27 wherein said amide is 3-cyclopentyl-N-thiazol-2-yl-2-[4-(2,2,2-trifluoro-ethanesulfonylamino)-phenyl]-propionamide.
31 . The amide of claim 26 wherein R is
wherein R 4 and R 5 are as above.
32 . The amide of claim 26 wherein R is aryl or nitro substituted aryl.
33 . The amide of claim 33 wherein said compound is 3-cyclopentyl-2-[4-(4-nitro-benzenesulfonylamino)-phenyl]-N-thiazol-2-yl-propionamide.Join the waitlist — get patent alerts
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