US4963561A
Expired / Lapsed
US
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Imidazopyridines, their preparation and use
Assignee: Sanofi SA
•
Filing: 1990-02-28
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Granted: 1990-10-16
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Expires: 2010-02-28
Abstract
Abstract Novel 1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-ones having an aryl or heteroaryl group in the 6-position, useful as phosphodiesterase inhibitors, are prepared by reacting a 2-amino-5-(aryl or heteroaryl)pyridine-3-carboxylic acid with diphenylphosphoryl azide. The compounds are of the formula <IMAGE> where R1 and R3 are hydrogen or lower-alkyl, R5 is lower-alkyl or fluorinated lower-alkyl, and Ar is 4- or 3-pyridinyl, or phenyl or substituted phenyl.
Inventors
- 👤 George Y. Lesher
- 👤 Edward R. Bacon
- 👤 Baldev Singh
- 👤 Gee-Hong Kuo
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 19:36
CPC Classifications
C; C07; C07D; C07D471/00; C07D471/02; C07D471/04
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
121 words
A compound of the formula ##STR6## wherein R 1 and R 3 are hydrogen or lower-alkyl; R 5 is lower-alkyl or fluorinated-lower-alkyl; and Ar is 4-or 3-pyridinyl, 4-or 6-quinolinyl, 4-pyrimidinyl, phenyl, or phenyl substituted in the 4-position by OH, NO 2 , NH 2 , NH(lower-alkyl), N(lower-alkyl) 2 , NHSO 2 -(alkyl of 1-8 carbons), NH-SO 2 -(phenyl or lower-alkylphenyl), NH-SO 2 -(fluorinated lower-alkyl), NH-SO 2 (CH 2 )hd 4N(loweralkyl) 2 , NH-SO 2 -(8-quinolinyl), NHCO-lower-alkyl, NHCO(fluorinated lower-alkyl) or NHCONH-lower-alkyl; or in the 4- and 3-positions by OH and NO 2 or OH and NH 2 , respectively; or a pharmaceutically acceptable acid-addition salt thereof; with the proviso that when R 5 is unsubstituted loweralkyl, Ar is other than 4-or 3-pyridinyl.
Claim 2
Dependent Claim
121 words
A compound of the formula ##STR6## wherein R 1 and R 3 are hydrogen or lower-alkyl; R 5 is lower-alkyl or fluorinated-lower-alkyl; and Ar is 4-or 3-pyridinyl, 4-or 6-quinolinyl, 4-pyrimidinyl, phenyl, or phenyl substituted in the 4-position by OH, NO 2 , NH 2 , NH(lower-alkyl), N(lower-alkyl) 2 , NHSO 2 -(alkyl of 1-8 carbons), NH-SO 2 -(phenyl or lower-alkylphenyl), NH-SO 2 -(fluorinated lower-alkyl), NH-SO 2 (CH 2 )hd 4N(loweralkyl) 2 , NH-SO 2 -(8-quinolinyl), NHCO-lower-alkyl, NHCO(fluorinated lower-alkyl) or NHCONH-lower-alkyl; or in the 4- and 3-positions by OH and NO 2 or OH and NH 2 , respectively; or a pharmaceutically acceptable acid-addition salt thereof; with the proviso that when R 5 is unsubstituted loweralkyl, Ar is other than 4-or 3-pyridinyl.
Claim 3
Dependent Claim
10 words
A compound according to claim 1 wherein Ar is 4-pyridinyl.
Claim 4
Dependent Claim
5 words
1,3-Dihydro-6-(4-pyridinyl)-5-trifluoromethyl-2H-imidazo[4,5-b]pyridin-2-one, according to claim 2.
Claim 5
Dependent Claim
5 words
1,3-Dihydro-6-(4-pyridinyl)-5-pentafluoroethyl-2H-imidazo[4,5-b]pyridin-2-one, according to claim 2.
Claim 6
Dependent Claim
5 words
1,3-Dihydro-6-(4-quinolinyl)-5-trifluoromethyl-2H-imidazo[4,5-b]pyridin-2-one, according to claim 1.
Claim 7
Dependent Claim
14 words
A compound according to claim 1 in which Ar is phenyl or substituted phenyl.
Claim 8
Dependent Claim
5 words
1,3-Dihydro-5-methyl-6-phenyl-2H-imidazo[4,5-b]pyridin-2-one, according to claim 6.
Claim 9
Dependent Claim
5 words
1,3-Dihydro-5-methyl-6-(4-nitrophenyl)-2Himidazo[4,5-b]pyridin-2-one, according to claim 6.
Claim 10
Dependent Claim
5 words
6-(4-Aminophenyl)-1,3-dihydro-5-methyl-2Himidazo[4,5-b]pyridin-2-one, according to claim 6.
Claim 11
Dependent Claim
5 words
1,3-Dihydro-5-methyl-6-[4-(trifluoroacetylamino)phenyl]-2H-imidazo[4,5-b]pyridin-2-one, according to claim 6.
Claim 12
Dependent Claim
5 words
6-[4-(Acetylamino)phenyl]-1,3-dihydro-5-methyl-2H-imidazo[4,5-b]pyridin-2-one, according to claim 6.
Claim 13
Dependent Claim
5 words
1,3-Dihydro-6-[4-(methanesulfonylamino)phenyl]-5-methyl-2H-imidazo[4,5-b]pyridin-2-one, according to claim 6.
Claim 14
Dependent Claim
5 words
6-[4-(Butanesulfonylamino)phenyl]-1,3-dihydro-5-methyl-2H-imidazo[4,5-b]pyridin-2-one, according to claim 6.
Claim 15
Dependent Claim
5 words
6-[4-(Butanecarbonylamino)phenyl]-1,3-dihydro-5-methyl-2H-imidazo[4,5-b]pyridin-2-one, according to claim 6.
Claim 16
Dependent Claim
5 words
1,3-Dihydro-5-methyl-6-[4-(p-toluenesulfonylamino)phenyl]-2H-imidazo[4,5-b]pyridin-2-one, according to claim 6.
Claim 17
Dependent Claim
5 words
1,3-Dihydro-6-[4-(hexanesulfonylamino)phenyl]-5-methyl-2H-imidazo[4,5-b]pyridin-2-one, according to claim 6.
Claim 18
Dependent Claim
5 words
1,3-Dihydro-6-[4-(8-quinolinylsulfonylamino)phenyl]-5-methyl-2H-imidazo[4,5-b]pyridin-2-one, according to claim 6.
Claim 19
Dependent Claim
5 words
1,3-Dihydro-6-[4-(N'-propylureido)phenyl]5-methyl-2H-imidazo[4,5-b]pyridin-2-one, according to claim 6.
Claim 20
Dependent Claim
30 words
A composition for effecting phosphodiesterase inhibition in a mammalian organism, which comprises an effective amount of a compound according to claim 1 in admixture with a suitable carrier or diluent.
Claim 21
Dependent Claim
22 words
A method for effecting phosphodiesterase inhibition in a mammalian organism which comprises administering to said organism a composition according to claim 19.
Claim 22
Dependent Claim
25 words
A method of treating congestive heart failure or hypertension in a mammalian organism which comprises administering to said organism a composition according to claim 19.
Claim 23
Dependent Claim
38 words
A process for preparing a compound according to claim 1 wherein R 1 and R 3 are hydrogen and Ar is 4-pyridinyl, 4-quinolinyl, 4-pyrimidinyl or phenyl, which comprises reacting a compound of the formula: ##STR7## with diphenylphosphoryl azide.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1993-10-15 | 1994-04-16 | 1994-10-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-10-15 | 1998-04-16 | 1998-10-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-10-15 | 2002-04-16 | 2002-10-16 | $7700.00 | Window Closed / Lapsed |