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US4701459A
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7-amino-1,3-dihydro-2H-imidazo[4,5-b]quinolin 2-ones and method for inhibiting phosphodiesterase and blood platelet aggregation
Assignee: Bristol Myers Co
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Filing: 1986-07-08
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Granted: 1987-10-20
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Expires: 2006-07-08
Abstract
Abstract Novel series of 2,3-dihydro-2-oxo-1H-imidazo[4,5-b]quinolinyl amine derivatives of Formula ##STR1## wherein R 1 is hydrogen, lower alkyl; R 2 is hydrogen, lower alkyl, lower alkoxy, halogen; R 3 is hydrogen, lower alkyl; R 4 is hydrogen, lower alkyl, alkanoyl, phenylalkanoyl wherein phenyl is optionally substituted with halogen, lower alkyl, lower alkoxy; R 3 and R 4 are joined together to form morpholinyl, piperidinyl or pyrrolidinyl optionally substituted with --CO 2 R 5 or ##STR2## wherein R 5 is hydrogen or lower alkyl, and R 6 is hydrogen, lower alkyl, cycloalkyl; 4-R 7 -piperazinyl wherein R 7 is --CO 2 R 8 wherein R 8 is lower alkyl, phenyl optionally substituted with up to 2 halogen, lower alkyl or lower alkoxy; phenylalkanoyl of 7 to 10 carbon wherein phenyl is unsubstituted or independently substituted with up to 2 halogen, lower alkyl, lower alkoxy. The compounds are cyclic AMP phosphodiesterase inhibitors and are particularly useful as inhibitors of blood platelet aggregation and/or as cardiotonic agents.
Inventors
- 👤 Nicholas A. Meanwell
- 👤 John J. Wright
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 03:03
CPC Classifications
C; C07; C07D; C07D471/00; C07D471/02; C07D471/04; A; A61; A61P; A61P43/00; A61P7/00; A61P7/02
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
168 words
A compound of the formula ##STR46## wherein R 1 is hydrogen, lower alkyl; R 2 is hydrogen, lower alkyl, lower alkoxy, halogen; R 3 is hydrogen, lower alkyl; R 4 is hydrogen, lower alkyl, alkanoyl of 1 to 6 carbon atoms, phenylalkanoyl of 7 to 10 carbon wherein phenyl is optionally substituted with halogen, lower alkyl, or lower alkoxy; R 3 and R 4 are joined together to form 1-morpholinyl, 1-piperidinyl or 1-pyrrolidinyl optionally substituted with --CO 2 R 5 or ##STR47## wherein R 5 is hydrogen or lower alkyl, and R 6 is hydrogen, lower alkyl, cycloalkyl of 5 to 7 carbon atoms; 1-(4-R 7 -piperazinyl) wherein R 7 is --CO 2 R 8 wherein R 8 is lower alkyl; phenyl optionally substituted with up to 2 halogen, lower alkyl or lower alkoxy; R 7 may also be phenylalkanoyl of 7 to 10 carbon atoms wherein phenyl is unsubstituted or independently substituted with up to 2 halogen, lower alkyl, lower alkoxy; or a pharmaceutically acceptable salt thereof.
Claim 2
Dependent Claim
168 words
A compound of the formula ##STR46## wherein R 1 is hydrogen, lower alkyl; R 2 is hydrogen, lower alkyl, lower alkoxy, halogen; R 3 is hydrogen, lower alkyl; R 4 is hydrogen, lower alkyl, alkanoyl of 1 to 6 carbon atoms, phenylalkanoyl of 7 to 10 carbon wherein phenyl is optionally substituted with halogen, lower alkyl, or lower alkoxy; R 3 and R 4 are joined together to form 1-morpholinyl, 1-piperidinyl or 1-pyrrolidinyl optionally substituted with --CO 2 R 5 or ##STR47## wherein R 5 is hydrogen or lower alkyl, and R 6 is hydrogen, lower alkyl, cycloalkyl of 5 to 7 carbon atoms; 1-(4-R 7 -piperazinyl) wherein R 7 is --CO 2 R 8 wherein R 8 is lower alkyl; phenyl optionally substituted with up to 2 halogen, lower alkyl or lower alkoxy; R 7 may also be phenylalkanoyl of 7 to 10 carbon atoms wherein phenyl is unsubstituted or independently substituted with up to 2 halogen, lower alkyl, lower alkoxy; or a pharmaceutically acceptable salt thereof.
Claim 3
Dependent Claim
14 words
The compound of claim 1 or a pharmaceutically accpetable salt thereof which is N-(2,3-dihydro-2-oxo-1H-imidazo[4,5-b]quinolin-7-yl)acetamide.
Claim 4
Dependent Claim
14 words
The compound of claim 1 or a pharmaceutically acceptable salt thereof which is 7-amino-1,3-dihydro-2H-imidazo[4,5-b]quinolin-2-one.
Claim 5
Dependent Claim
14 words
The compound of claim 1 or a pharmaceutically acceptable salt thereof which is N-(2,3-dihydro-2-oxo-1H-imidazo[4,5-b]quinolin-7-yl)benzamide.
Claim 6
Dependent Claim
14 words
The compound of claim 1 or a pharmaceutically acceptable salt thereof which is 1,3-dihydro-7-(1-piperidinyl)-2H-imidazo[4,5-b]quinolin-2-one.
Claim 7
Dependent Claim
14 words
The compound of claim 1 or a pharmaceutically acceptable salt thereof which is 1,3-dihydro-7-(1-pyrrolidinyl)-2H-imidazo[4,5-b]quinolin-2-one.
Claim 8
Dependent Claim
14 words
The compound of claim 1 or a pharmaceutically acceptable salt thereof which is 7-(diethylamino)-1,3-dihydro-2H-imidazo[4,5-b]quinolin-2-one.
Claim 9
Dependent Claim
14 words
The compound of claim 1 or a pharmaceutically acceptable salt thereof which is 1,3-dihydro-7-(4-morpholinyl)-2H-imidazo[4,5-b]quinolin-2-one.
Claim 10
Dependent Claim
15 words
The compound of claim 1 or a pharmaceutically acceptable salt thereof which is methyl 1-(2,3-dihydro-2-oxo-1H-imidazo[4,5-b]quinolin-7-yl)-4-piperidinecarboxylate.
Claim 11
Dependent Claim
15 words
The compound of claim 1 or a pharmaceutically acceptable salt thereof which is 1-(2,3-dihydro-2-oxo-1H-imidazo[4,5-b]quinolin-7-yl)-4-piperidinecarboxylic acid.
Claim 12
Dependent Claim
15 words
The compound of claim 1 or a pharmaceutically acceptable salt thereof which is ethyl 4-(2,3-dihydro-2-oxo-1H-imidazo[4,5-b]quinolin-7-yl)-1-piperazinecarboxylate.
Claim 13
Dependent Claim
14 words
The compound of claim 1 or a pharmaceutically acceptable salt thereof which is 1-benzoyl-4-(2,3-dihydro-2-oxo-1H-imidazo[4,5-b]quinolin-7-yl)piperazine.
Claim 14
Dependent Claim
14 words
The compound of claim 1 or a pharmaceutically acceptable salt thereof which is 1-(2,3-dihydro-2-oxo-1H-imidazo[4,5-b]quinolin-7-yl)-4-(3,4-dimethoxybenzoyl)piperazine.
Claim 15
Dependent Claim
14 words
The compound of claim 1 or a pharmaceutically acceptable salt thereof which is 1,3-dihydro-7-(4-phenyl-1-piperazinyl)-2H-imidazo[4,5-b]quinolin-2-one.
Claim 16
Dependent Claim
14 words
The compound of claim 1 or a pharmaceutically acceptable salt thereof which is N-cyclohexyl-1-(2,3-dihydro-2-oxo-1H-imidazo[4,5-b]quinolin-7-yl)-N-methyl-4-piperidinecarboxamide.
Claim 17
Dependent Claim
27 words
A method for inhibiting phosphodiesterase in a mammal which comprises administering a therapeutically effective amount of a compound of claim 1 or a pharmaceutically acceptable salt thereof.
Claim 18
Dependent Claim
29 words
The pharmaceutical composition for inhibiting phosphodiesterase comprising a therapeutically effective amount of a compound of claim 1 or a pharmaceutically acceptable acid addition salt thereof and a pharmaceutical carrier.
Claim 19
Dependent Claim
26 words
The pharmaceutical composition comprising a therapeutically effective amount of a compound of claim 1 or a pharmaceutically acceptable acid addition salt thereof and a pharmaceutical carrier.
Claim 20
Dependent Claim
29 words
A method for inhibiting blood platelet aggregation in a mammal which comprises administering a therapeutically effective amount of a compound of claim 1 or a pharmaceutically acceptable salt thereof.
Claim 21
Dependent Claim
31 words
The pharmaceutical composition for inhibiting blood platelet aggregation comprising a therapeutically effective amount of a compound of claim 1 or a pharmaceutically acceptable acid addition salt thereof and a pharmaceutical carrier.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1990-10-19 | 1991-04-20 | 1991-10-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-10-19 | 1995-04-20 | 1995-10-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-10-19 | 1999-04-20 | 1999-10-20 | $7700.00 | Window Closed / Lapsed |