US4321384A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Antihypertensive agents
Assignee: Wyeth LLC
•
Filing: 1981-02-27
•
Granted: 1982-03-23
•
Expires: 2001-02-27
Abstract
Abstract 1,4,5,6,7,8-hexahydro-2-alkyl-4-aryl-5-oxo-1,7-naphthyridine-3-carboxylic acid esters and pharmaceutically acceptable salts thereof are useful antihypertensive agents.
Inventors
- 👤 Theodore S. Sulkowski
- 👤 James L. Bergey
- 👤 Albert A. Mascitti
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 09:29
CPC Classifications
C; C07; C07D; C07D471/00; C07D471/02; C07D471/04; A; A61; A61P; A61P9/00; A61P9/06; A61P9/08; A61P9/10; A61P9/12
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
222 words
A compound of the formula: ##STR6## in which R is hydrogen or alkyl of 1 to 6 carbon atoms; R 2 is alkyl of 1 to 6 carbon atoms; R 3 is alkyl of 1 to 6 carbon atoms, alkoxyalkyl in which each alkyl moiety has 1 to 6 carbon atoms, --CH 2 CF 3 , --CH 2 CH 2 CF 3 or ##STR7## where R 9 is hydrogen or alkyl of 1 to 6 carbon atoms and R 10 is alkyl of 1 to 6 carbon atoms or arylalkyl of 7 to 10 carbon atoms and R 9 and R 10 taken with the nitrogen atom to which they are attached form a pyrrolidinyl, imidazolidinyl, piperidyl, piperazinyl, 4-alkylpiperazinyl in which the alkyl group contains from 1 to 6 carbon atoms or morpholinyl heterocycle, and n is one of the integers 0, 1 or 2; R 6 and R 8 are, independently, hydrogen, alkyl of 1 to 6 carbon atoms, halo, trifluoromethyl, alkoxy of 1 to 6 carbon atoms, alkylthio of 1 to 6 carbon atoms, cyano or nitro; R 7 is hydrogen, alkyl of 1 to 6 carbon atoms, halo, trifluoromethyl, cyano or nitro; and R 6 and R 7 when in ortho position to each other and taken together are butadienylene, tetramethylene or trimethylene; or a pharmaceutically acceptable salt thereof.
Claim 2
Dependent Claim
222 words
A compound of the formula: ##STR6## in which R is hydrogen or alkyl of 1 to 6 carbon atoms; R 2 is alkyl of 1 to 6 carbon atoms; R 3 is alkyl of 1 to 6 carbon atoms, alkoxyalkyl in which each alkyl moiety has 1 to 6 carbon atoms, --CH 2 CF 3 , --CH 2 CH 2 CF 3 or ##STR7## where R 9 is hydrogen or alkyl of 1 to 6 carbon atoms and R 10 is alkyl of 1 to 6 carbon atoms or arylalkyl of 7 to 10 carbon atoms and R 9 and R 10 taken with the nitrogen atom to which they are attached form a pyrrolidinyl, imidazolidinyl, piperidyl, piperazinyl, 4-alkylpiperazinyl in which the alkyl group contains from 1 to 6 carbon atoms or morpholinyl heterocycle, and n is one of the integers 0, 1 or 2; R 6 and R 8 are, independently, hydrogen, alkyl of 1 to 6 carbon atoms, halo, trifluoromethyl, alkoxy of 1 to 6 carbon atoms, alkylthio of 1 to 6 carbon atoms, cyano or nitro; R 7 is hydrogen, alkyl of 1 to 6 carbon atoms, halo, trifluoromethyl, cyano or nitro; and R 6 and R 7 when in ortho position to each other and taken together are butadienylene, tetramethylene or trimethylene; or a pharmaceutically acceptable salt thereof.
Claim 3
Dependent Claim
11 words
The compound of claim 1 which is 1,4,5,6,7,8-hexahydro-2,7-dimethyl-4-(2-nitrophenyl)-5-oxo-1,7-naphthyridine-3-carboxylic acid methyl ester.
Claim 4
Dependent Claim
12 words
The compound of claim 1 in which is 1,4,5,6,7,8-hexahydro-2,7-dimethyl-4-(2-methylphenyl)-5-oxo-1,7-naphthyridine-3-carboxylic acid methyl ester.
Claim 5
Dependent Claim
11 words
The compound of claim 1 which is 1,4,5,6,7,8-hexahydro-2,7-dimethyl-5-oxo-4-[2-(trifluoromethyl)phenyl]-1,7-naphthyridine-3-carboxylic acid methyl ester.
Claim 6
Dependent Claim
11 words
The compound of claim 1 which is 1,4,5,6,7,8-hexahydro-2,7-dimethyl-4-(3-nitrophenyl)-5-oxo-1,7-naphthyridine-3-carboxylic acid methyl ester.
Claim 7
Dependent Claim
11 words
The compound of claim 1 which is 1,4,5,6,7,8-hexahydro-2-methyl-4-(2-methylphenyl)-5-oxo-1,7-naphthyridine-3-carboxylic acid methyl ester.
Claim 8
Dependent Claim
11 words
The compound of claim 1 which is 4-(2-chlorophenyl)-1,4,5,6,7,8-hexahydro-2,7-dimethyl-5-oxo-1,7-naphthyridine-3-carboxylic acid methyl ester.
Claim 9
Dependent Claim
11 words
The compound of claim 1 which is 4-(2,6-dichlorophenyl)-1,4,5,6,7,8-hexahydro-2,7-dimethyl-5-oxo-1,7-naphthyridine-3-carboxylic acid methyl ester.
Claim 10
Dependent Claim
11 words
The compound of claim 1 which is 4-(2,5-dimethylphenyl)-1,4,5,6,7,8-hexahydro-2,7-dimethyl-5-oxo-1,7-naphthyridine-3-carboxylic acid methyl ester.
Claim 11
Dependent Claim
11 words
The compound of claim 1 which is 1,4,5,6,7,8-hexahydro-2-methyl-5-oxo-4-[2-(trifluoromethyl)phenyl]-1,7-naphthyridine-3-carboxylic acid methyl ester.
Claim 12
Dependent Claim
11 words
The compound of claim 1 which is 1,4,5,6,7,8-hexahydro-2-methyl-4-(3-nitrophenyl)-5-oxo-1,7-naphthyridine-3-carboxylic acid methyl ester.
Claim 13
Dependent Claim
11 words
The compound of claim 1 which is 1,4,5,6,7,8-hexahydro-2-methyl-5-oxo-4-[3-(trifluoromethyl)phenyl]-1,7-naphthyridine-3-carboxylic acid methyl ester.
Claim 14
Dependent Claim
11 words
The compound of claim 1 which is 4-(2-fluorophenyl)-1,4,5,6,7,8-hexahydro-2-methyl-5-oxo-1,7-naphthyridine-3-carboxylic acid methyl ester.
Claim 15
Dependent Claim
11 words
The compound of claim 1 which is 4-(3-cyanophenyl)-1,4,5,6,7,8-hexahydro-2,7-dimethyl-5-oxo-1,7-naphthyridine-3-carboxylic acid methyl ester.
Claim 16
Dependent Claim
11 words
The compound of claim 1 which is 4-(2,3-dimethylphenyl)-1,4,5,6,7,8-hexahydro-2,7-dimethyl-5-oxo-1,7-naphthyridine-3-carboxylic acid methyl ester.
Claim 17
Dependent Claim
11 words
The compound of claim 1 which is 4-[2-(n-butyl)-phenyl]-1,4,5,6,7,8-hexahydro-2-methyl-5-oxo-1,7-naphthyridine-3-carboxylic acid methyl ester.
Claim 18
Dependent Claim
11 words
The compound of claim 1 which is 4-(2,3-dimethylphenyl)-1,4,5,6,7,8-hexahydro-2-methyl-5-oxo-1,7-naphthyridine-3-carboxylic acid methyl ester.
Claim 19
Dependent Claim
215 words
A compound of the formula: ##STR8## in which PhCH 2 is benzyl; R 2 is alkyl of 1 to 6 carbon atoms; R 3 is alkyl of 1 to 6 carbon atoms, alkoxyalkyl in which each alkyl moiety has 1 to 6 carbon atoms, --CH 2 CF 3 , --CH 2 CH 2 CF 3 or ##STR9## where R 9 is hydrogen or alkyl of 1 to 6 carbon atoms and R 10 is alkyl of 1 to 6 carbon atoms or arylalkyl of 7 to 10 carbon atoms and R 9 and R 10 taken with the nitrogen atom to which they are attached form a pyrrolidinyl, imidazolidinyl, piperidyl, piperazinyl, 4-alkylpiperazinyl in which the alkyl group contains from 1 to 6 carbon atoms or morpholinyl heterocycle, and n is one of the integers 0, 1 or 2; R 6 and R 8 are, independently, hydrogen, alkyl of 1 to 6 carbon atoms, halo, trifluoromethyl, alkoxy of 1 to 6 carbon atoms, alkylthio of 1 to 6 carbon atoms, cyano or nitro; R 7 is hydrogen, alkyl of 1 to 6 carbon atoms, halo, trifluoromethyl, cyano or nitro; and R 6 and R 7 when in ortho position to each other and taken together are butadienylene, tetramethylene or trimethylene; or a pharmaceutically acceptable salt thereof.
Claim 20
Dependent Claim
215 words
A compound of the formula: ##STR8## in which PhCH 2 is benzyl; R 2 is alkyl of 1 to 6 carbon atoms; R 3 is alkyl of 1 to 6 carbon atoms, alkoxyalkyl in which each alkyl moiety has 1 to 6 carbon atoms, --CH 2 CF 3 , --CH 2 CH 2 CF 3 or ##STR9## where R 9 is hydrogen or alkyl of 1 to 6 carbon atoms and R 10 is alkyl of 1 to 6 carbon atoms or arylalkyl of 7 to 10 carbon atoms and R 9 and R 10 taken with the nitrogen atom to which they are attached form a pyrrolidinyl, imidazolidinyl, piperidyl, piperazinyl, 4-alkylpiperazinyl in which the alkyl group contains from 1 to 6 carbon atoms or morpholinyl heterocycle, and n is one of the integers 0, 1 or 2; R 6 and R 8 are, independently, hydrogen, alkyl of 1 to 6 carbon atoms, halo, trifluoromethyl, alkoxy of 1 to 6 carbon atoms, alkylthio of 1 to 6 carbon atoms, cyano or nitro; R 7 is hydrogen, alkyl of 1 to 6 carbon atoms, halo, trifluoromethyl, cyano or nitro; and R 6 and R 7 when in ortho position to each other and taken together are butadienylene, tetramethylene or trimethylene; or a pharmaceutically acceptable salt thereof.
Claim 21
Dependent Claim
11 words
The compound of claim 18 which is 1,4,5,6,7,8-hexahydro-2-methyl-4-(2-methylphenyl)-5-oxo-7-(phenylmethyl)-1,7-naphthyridine-3-carboxylic acid methyl ester.
Claim 22
Dependent Claim
11 words
The compound of claim 18 which is 1,4,5,6,7,8-hexahydro-2-methyl-5-oxo-7-(phenylmethyl)-4-[2-(trifluoromethyl)-phenyl]-1,7-naphthyridine-3-carboxylic acid methyl ester.
Claim 23
Dependent Claim
11 words
The compound of claim 18 which is 1,4,5,6,7,8-hexahydro-2-methyl-4-(3-nitrophenyl)-5-oxo-7-(phenylmethyl)-1,7-naphthyridine-3-carboxylic acid methyl ester.
Claim 24
Dependent Claim
11 words
The compound of claim 18 which is 4-[2-(n-butyl)-phenyl]-1,4,5,6,7,8-hexahydro-2-methyl-5-oxo-7-(phenylmethyl)-1,7-naphthyridine-3-carboxylic acid methyl ester.
Claim 25
Dependent Claim
11 words
The compound of claim 18 which is 4-(2,3-dimethylphenyl)-1,4,5,6,7,8-hexahydro-2-methyl-5-oxo-7-(phenylmethyl)-1,7-naphthyridine-3-carboxylic acid methyl ester.
Claim 26
Dependent Claim
11 words
The compound of claim 18 which is 1,4,5,6,7,8-hexahydro-2-methyl-5-oxo-7-phenylmethyl-4-[2-(trifluoromethyl)phenyl]-1,7-naphthyridine-3-carboxylic acid, 2-(N-benzyl-N-methyl)aminoethyl ester.
References Cited (Backward Citations)
US3429887A
Cited
US3506668A
Cited
US3325505A
Cited
US3441648A
Cited
US3600394A
Cited
US3590036A
Cited
US3773773A
Cited
US3963736A
Cited
US3673193A
Cited
US3799934A
Cited
US4022898A
Cited
US4038399A
Cited
BE843576A
Cited
US4177278A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-03-22 | 1985-09-21 | 1986-03-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-03-22 | 1989-09-21 | 1990-03-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-03-22 | 1993-09-21 | 1994-03-23 | $7700.00 | Window Closed / Lapsed |