Patent DE811717C successfully refreshed from Google Patents.
US4344949A
Expired / Lapsed
US
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Substituted acyl derivatives of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acids
Assignee: Warner Lambert Co LLC
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Filing: 1981-02-20
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Granted: 1982-08-17
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Expires: 2001-02-20
Abstract
Abstract Substituted acyl derivatives of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acids and the pharmaceutically acceptable salts thereof are produced by coupling a suitably substituted 1,2,3,4-tetrahydroisoquinoline with a suitably substituted amino acid and when desired hydrolyzing or removing protecting groups of the resulting product. The compounds of the invention, their salts and pharmaceutical compositions thereof are useful as antihypertensive agents.
Inventors
- 👤 Milton L. Hoefle
- 👤 Sylvester Klutchko
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 02:43
CPC Classifications
C; C07; C07D; C07D217/00; C07K; C07K5/00; C07K5/02; C07K5/022; C07K5/0222; A; A61; A61P; A61P9/00; A61P9/12; C07D217/22; C07D217/26; A61K; A61K38/00; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
118 words
A substituted acyl compound of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid having the formula ##STR5## where R is hydrogen, lower alkyl or phenylalkyl; R 1 is hydrogen, lower alkyl, or benzyl; R 2 is hydrogen, or lower alkyl and Ar is phenyl, or substituted phenyl having 1 or 2 substituents selected from the group consisting of fluorine, chlorine, bromine, lower alkyl, lower alkoxy, hydroxy or amino; X and Y are independently hydrogen, lower alkyl, lower alkoxy, lower alkylthio, lower alkylsulfinyl, lower alkylsulfonyl, hydroxy, or X and Y together are methylenedioxy; and m is 0 to 3; wherein lower alkyl, alkyl in the group phenylalkyl; and lower alkoxy has 1 to 4 straight or branched carbon atoms and the pharmaceutically acceptable salts thereof.
Claim 2
Dependent Claim
118 words
A substituted acyl compound of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid having the formula ##STR5## where R is hydrogen, lower alkyl or phenylalkyl; R 1 is hydrogen, lower alkyl, or benzyl; R 2 is hydrogen, or lower alkyl and Ar is phenyl, or substituted phenyl having 1 or 2 substituents selected from the group consisting of fluorine, chlorine, bromine, lower alkyl, lower alkoxy, hydroxy or amino; X and Y are independently hydrogen, lower alkyl, lower alkoxy, lower alkylthio, lower alkylsulfinyl, lower alkylsulfonyl, hydroxy, or X and Y together are methylenedioxy; and m is 0 to 3; wherein lower alkyl, alkyl in the group phenylalkyl; and lower alkoxy has 1 to 4 straight or branched carbon atoms and the pharmaceutically acceptable salts thereof.
Claim 3
Dependent Claim
54 words
A substituted acyl compound of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid according to claim 1 having the formula ##STR6## where R is hydrogen, t-butyl, or benzyl; R 1 is hydrogen or lower alkyl; R 2 is hydrogen, methyl or ethyl; X and Y are independently hydrogen, lower alkyl, hydroxy or lower alkoxy; and the pharmaceutically acceptable salts thereof.
Claim 4
Dependent Claim
29 words
A substituted acyl compound of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid according to claim 2 having the formula ##STR7## where R 2 is hydrogen, methyl or ethyl and the pharmaceutically acceptable salts thereof.
Claim 5
Dependent Claim
29 words
A substituted acyl compound of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid according to claim 2 having the formula ##STR8## where R 2 is hydrogen, methyl or ethyl and the pharmaceutically acceptable salts thereof.
Claim 6
Dependent Claim
14 words
The compound according to claim 2 which is 2-[2-[[1-(ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-3-isoquinolinecarboxylic acid, phenylmethyl ester, maleate (S,S,S).
Claim 7
Dependent Claim
14 words
The compound according to claim 2 which is 2-[2-[[1-(ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]-1,2,3,4-tetrahydro-3-isoquinoline-carboxylic acid, phenylmethyl ester, maleate (S,S,S).
Claim 8
Dependent Claim
13 words
The compound according to claim 2 which is 2-[2-[[1-(ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid, 1,1-dimethylethyl ester, (S,S,S).
Claim 9
Dependent Claim
13 words
The compound according to claim 3 which is 2-[2-[[1-(ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-3-isoquinolinecarboxylic acid, hydrochloride, hydrate (S,S,S).
Claim 10
Dependent Claim
13 words
The compound according to claim 3 which is 2-[2-[(1-carboxy-3-phenylpropyl)amino]-1-oxopropyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-3-isoquinolinecarboxylic acid, hydrochloride, hydrate (S,S,S).
Claim 11
Dependent Claim
13 words
The compound according to claim 4 which is 2-[2-[[1-(ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid, hydrochloride, hydrate (S,S,S).
Claim 12
Dependent Claim
13 words
The compound according to claim 4 which is 2-[2-[(1-carboxy-3-phenylpropyl)amino]-1-oxopropyl]-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid, hydrochloride, hemihydrate (S,S,S).
Claim 13
Dependent Claim
13 words
The compound according to claim 3 which is 2-[2-[[1-(ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-3-isoquinoline carboxylic acid, hydrochloride, (S,S,S).
Claim 14
Dependent Claim
13 words
The compound according to claim 4 which is 2-[2-[[1-(ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]-1,2,3,4-tetrahydro-3-isoquinoline carboxylic acid, hydrochloride (S,S,S).
Claim 15
Dependent Claim
37 words
A pharmaceutical composition comprising 10 to 500 mg of a substituted acyl compound of a 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid or a mixture of compounds according to claim 1 or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier.
Claim 16
Dependent Claim
28 words
A method of treating hypertension by administering an effective amount of a substituted acyl compound of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid according to claim 1 or a pharmaceutically acceptable salt thereof.
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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) | 1985-08-16 | 1986-02-15 | 1986-08-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-08-16 | 1990-02-15 | 1990-08-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-08-16 | 1994-02-15 | 1994-08-17 | $7700.00 | Window Closed / Lapsed |