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US5232920A Expired / Lapsed US ⏱️ 0.0 years remaining

N-(mercaptoalkyl)amides

Assignee: Merck Sharp & Dohme LLC
•
Filing: 1990-12-21
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Granted: 1993-08-03
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Expires: 2010-12-21
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Abstract

Abstract Novel N-(mercaptoalkyl)amides of the formula <IMAGE> wherein R1 is lower alkyl, cyclolower alkyl, aryl or heteroaryl; R2 is (COR3)-aryl, heteroaryl, substituted (COR3)-aryl or substituted heteroaryl, wherein the substituents are 1-3 substituents selected from the group consisting of carboxy, alkoxycarbonyl, lower alkyl, hydroxy, halo, lower alkoxy, cyclolower alkyl, cyano, trifluoromethyl, phenyl, phenoxy and phenylthio; R3 is -OR4 or -NR4R5; R4 and R5 are independently selected from the group consisting of hydrogen, lower alkyl, hydroxy lower alkyl, lower alkoxy lower alkyl and aryl lower alkyl, or R4 and R5 together with the nitrogen to which they are attached form a 5-, 6- or 7-membered ring; Q is hydrogen or R6CO-; R6 is hydrogen, lower alkyl or aryl; and m is 1 or 2; and the pharmaceutically acceptable salts thereof useful in the treatment of cardiovascular disorders, nephrotoxicity and pain conditions and combinations of N-(mercaptoalkyl)amides and atrial natriuretic factors or angiotensin converting enzyme inhibitors useful for treating cardiovascular disorders are disclosed.

Inventors

  • 👤 Bernard R. Neustadt

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-05 19:38
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/78; C07D213/81; A; A61; A61P; A61P25/00; A61P25/04; A61P43/00; A61P7/00; A61P7/10; A61P9/00; A61P9/04; A61P9/12; C07C; C07C323/00; C07C323/23; C07C323/39; C07C323/40; C07C323/42; C07C327/00; C07C327/20; C07C327/30

Claims Analysis

Total Claims: 9
Claim 1
Independent Claim 144 words
A compound having the structural formula ##STR37## wherein R 1 is lower alkyl, cyclolower alkyl or aryl; R 2 is (COR 3 )-aryl or substituted (COR 3 )-aryl, wherein the substituents are 1-3 substituents selected from the group consisting of carboxy, alkoxycarbonyl, lower alkyl, hydroxy, nitro, halo, lower alkoxy, cyclolower alkyl, cyano, trifluoromethyl, phenyl, phenoxy and phenylthio; R 3 is --OR 4 or --NR 4 R 5 ; R 4 and R 5 are independently selected from the group consisting of hydrogen, lower alkyl, hydroxy lower alkyl, lower alkoxy lower alkyl and aryl lower alkyl, or R 4 and R 5 together with the nitrogen to which they are attached form a 5-, 6- or 7-membered ring; Q is hydrogen or R 6 CO-; R 6 is hydrogen, lower alkyl or aryl; and m is 1 or 2; and the pharmaceutically acceptable salts thereof.
Claim 2
Dependent Claim 144 words
A compound having the structural formula ##STR37## wherein R 1 is lower alkyl, cyclolower alkyl or aryl; R 2 is (COR 3 )-aryl or substituted (COR 3 )-aryl, wherein the substituents are 1-3 substituents selected from the group consisting of carboxy, alkoxycarbonyl, lower alkyl, hydroxy, nitro, halo, lower alkoxy, cyclolower alkyl, cyano, trifluoromethyl, phenyl, phenoxy and phenylthio; R 3 is --OR 4 or --NR 4 R 5 ; R 4 and R 5 are independently selected from the group consisting of hydrogen, lower alkyl, hydroxy lower alkyl, lower alkoxy lower alkyl and aryl lower alkyl, or R 4 and R 5 together with the nitrogen to which they are attached form a 5-, 6- or 7-membered ring; Q is hydrogen or R 6 CO-; R 6 is hydrogen, lower alkyl or aryl; and m is 1 or 2; and the pharmaceutically acceptable salts thereof.
Claim 3
Dependent Claim 19 words
A compound of claim 1 wherein R 1 is phenyl or lower alkyl substituted phenyl and m is 1.
Claim 4
Dependent Claim 13 words
A compound of claim 1 wherein R 3 is hydroxy or lower alkoxy.
Claim 5
Dependent Claim 18 words
A compound of claim 1 wherein R 2 is (COR 3 )-phenyl, nitro or carboxy-substituted (COR 3 )-phenyl.
Claim 6
Dependent Claim 11 words
A compound of claim 1 wherein Q is hydrogen or acyl.
Claim 7
Dependent Claim 23 words
A compound of claim 1 which is: methyl 4-[N-[1(R)-acetylthio-3-(2-methylphenyl)-2-propyl]aminocarbonyl]benzoate; 4-[N-[1(R)-mercapto-3-(2-methylphenyl)-2-propyl]aminocarbonyl]benzoic acid; methyl 3-[N-[1(R)-acetylthio-3-(2-methylphenyl)-2-propyl]aminocarbonyl]benzoate; 3-[N-[1(R)-mercapto-3-(2-methylphenyl)-2-propyl]aminocarbonyl]benzoic acid; methyl 3-[N-[1(R)-acetylthio-3-(2-methylphenyl)-2-propyl]aminocarbonyl]-5-nitrobenzoate; 3-[N-[1(R)-mercapto-3-(2-methylphenyl)-2-propyl]aminocarbonyl]-5-nitrobenzoic acid; 4-[N-[1(R)-acetylthio-3-(2-methylphenyl)-2-propyl]aminocarbonyl]phthalic acid; 4-[N-[1(R)-mercapto-3-(2-methylphenyl)-2-propyl]aminocarbonyl]phthalic acid.
Claim 8
Dependent Claim 30 words
A method for treating hypertension or congestive heart failure in mammals comprising administering to a mammal in need of such treatment an effective amount of a compound of claim 1.
Claim 9
Dependent Claim 18 words
A pharmaceutical composition comprising an effective amount of a compound of claim 1 in a pharmaceutically acceptable carrier.

References Cited (Backward Citations)

US4256761A Cited
US4256761B1 Cited
GB2095682A Cited
US4470973A Cited
FR2589468A1 Cited

USPTO Annuity & Maintenance Windows

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