EP0318859A2
Expired / Lapsed
EP
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N-substituted mercaptopropanamide derivatives
Assignee: Sumitomo Pharma Co Ltd
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Filing: 1988-11-25
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Granted: —
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Expires: 2008-11-25
Abstract
Abstract Novel N-substituted mercaptopropanamide derivatives of the formula: wherein R₁ is mercapto or a group convertible into mercapto when cleaved within the biobody, W is hydrogen atom, an alkyl or an aralkyl, R₂ is an aryl which may optionally have substituent(s), a heterocyclic group which may optionally have substituent(s), or an alkyl which may optionally have substituent(s), X is a cycloalkylene, a cycloalkylidene, or a phenylene which may optionally have substituent(s) or may optionally be fused with other ring, and R₃ is carboxyl or a group convertible into carboxyl when cleaved within the biobody, or a pharmaceutically acceptable salt thereof, and a solid solution of said N-substituted mercaptopropanamide derivative with an amino acid, which have excellent enkephalinase inhibitory activity and are useful for the treatment of mild to moderate pain, and a pharmaceutical composition containing said compounds as an active ingredient, and processes for preparing these compounds.
Inventors
- 👤 Tetsutaro Mimura
- 👤 Yasuhisa Nakamura
- 👤 Junko Nishino
- 👤 Tadahiro Sawayama
- 👤 Takashi Sasagawa
- 👤 Takashi Deguchi
- 👤 Hideo Nakamura
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-06 02:57
CPC Classifications
C; C07; C07D; C07D265/00; C07D265/28; C07D265/30; C07C; C07C229/00; C07C229/02; C07C229/04; C07C229/06; C07C229/08; C07C229/24; C07C229/26; C07C229/34; C07C229/52; C07C229/54; C07C229/60; C07C323/00; C07C323/50; C07C323/51; C07C323/60; C07C327/00; C07C327/02; C07C327/04; C07C327/06; C07C327/12; C07C327/16; C07C327/20; C07C327/24; C07C327/32; C07C329/00; C07C329/02; C07C329/04; C07C329/06; C07C333/00; C07C333/02; C07C333/06; C07D213/00; C07D213/02; C07D213/04; C07D213/24; C07D213/44; C07D213/46; C07D213/50; C07D261/00; C07D261/20; C07D295/00; C07D295/04; C07D295/08; C07D295/084; C07D295/088; C07D295/14; C07D295/155; C07D307/00; C07D307/02; C07D307/34; C07D307/56; C07D307/68; C07D333/00; C07D333/02; C07D333/04; C07D333/06; C07D333/22; C07D333/26; C07D333/38; C07C2601/00; C07C2601/02; C07C2601/06; C07C2601/08; C07C2601/12; C07C2601/16
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
315 words
A process for preparing a N-substituted mercaptopropanamide derivative of the formula: wherein R₁ is mercapto or a group convertible into mercapto when cleaved within the biobody, W is hydrogen atom, an alkyl or an aralkyl, R₂ is an aryl which may optionally have substituent(s), a heterocyclic group which may optionally have substituent(s), or an alkyl which may optionally have substituent(s), X is a cycloalkylene, a cycloalkylidene, or a phenylene which may optionally have substituent(s) or may optionally be fused with other ring, and R₃ is carboxyl or a group convertible into carboxyl when cleaved within the biobody, or a pharmaceutically acceptable salt thereof, comprising (1) reacting a compound of the formula: H₂N-X-R₃ (II) wherein X and R₃ as defined above with a compound of the formula: wherein R₁, R₂ and W are as defined above, or a reactive derivative thereof, or (2) reacting a compound of the formula: wherein R₂, W, X and R₃ are as defined above, or a compound of the formula: wherein B is a reacative group, and R₂, W, X and R₃ as defined above, with a compound of the formula: R₁-H (VI) wherein R₁ as defined above, or (3) in case of the compound (I) wherein R₃ is a group convertible into carboxyl when cleaved in the biobody, reacting a compound of the formula: wherein R₁, R₂, W and X are as defined above, or a reactive derivative thereof with a compound of the formula: R₇-OH (VIII) wherein R₇ is a cycloalkyl, a cycloalkyl-alkyl, an alkoxycarbonylalkyl, an N-substituted or unsubstituted aminocarbonylalkyl, an acyloxyalkyl, a substituted or unsubstituted alkyl, an alkoxycarbonyl, or an aryl, aralkyl, aryloxyalkyl, heterocyclic group, heterocyclic group-substituted alkyl, heterocyclic amidoalkyl, or benzene-fused lactonyl, these ring-containing groups having optionally substituent(s), or an N-substituted or unsubstituted aminocarbonyl, or with a compound of the formula: R₈-NH₂ (IX) wherein R₈ is a residue of natural amino acids which may optionally be esterified.
Claim 2
Dependent Claim
315 words
A process for preparing a N-substituted mercaptopropanamide derivative of the formula: wherein R₁ is mercapto or a group convertible into mercapto when cleaved within the biobody, W is hydrogen atom, an alkyl or an aralkyl, R₂ is an aryl which may optionally have substituent(s), a heterocyclic group which may optionally have substituent(s), or an alkyl which may optionally have substituent(s), X is a cycloalkylene, a cycloalkylidene, or a phenylene which may optionally have substituent(s) or may optionally be fused with other ring, and R₃ is carboxyl or a group convertible into carboxyl when cleaved within the biobody, or a pharmaceutically acceptable salt thereof, comprising (1) reacting a compound of the formula: H₂N-X-R₃ (II) wherein X and R₃ as defined above with a compound of the formula: wherein R₁, R₂ and W are as defined above, or a reactive derivative thereof, or (2) reacting a compound of the formula: wherein R₂, W, X and R₃ are as defined above, or a compound of the formula: wherein B is a reacative group, and R₂, W, X and R₃ as defined above, with a compound of the formula: R₁-H (VI) wherein R₁ as defined above, or (3) in case of the compound (I) wherein R₃ is a group convertible into carboxyl when cleaved in the biobody, reacting a compound of the formula: wherein R₁, R₂, W and X are as defined above, or a reactive derivative thereof with a compound of the formula: R₇-OH (VIII) wherein R₇ is a cycloalkyl, a cycloalkyl-alkyl, an alkoxycarbonylalkyl, an N-substituted or unsubstituted aminocarbonylalkyl, an acyloxyalkyl, a substituted or unsubstituted alkyl, an alkoxycarbonyl, or an aryl, aralkyl, aryloxyalkyl, heterocyclic group, heterocyclic group-substituted alkyl, heterocyclic amidoalkyl, or benzene-fused lactonyl, these ring-containing groups having optionally substituent(s), or an N-substituted or unsubstituted aminocarbonyl, or with a compound of the formula: R₈-NH₂ (IX) wherein R₈ is a residue of natural amino acids which may optionally be esterified.
Claim 3
Dependent Claim
20 words
The process of claim 1 for the production of compounds wherein X is a (C₁-C₄) alkyl-substituted phenylene or unsubstituted phenylene.
Claim 4
Dependent Claim
29 words
The process of claim 1 for the production of compounds wherein R₁ is mercapto or acetylthio, W is hydrogen atom, R₂ is phenyl or isopropyl, and R₃ is carboxyl.
Claim 5
Dependent Claim
13 words
The process of claim 1 for the production of the compound 3-[(2-acetylthiomethyl-3-phenylpropionyl)amino]-5-methylbenzoic acid.
Claim 6
Dependent Claim
13 words
The process of claim 1 for the production of the compound 3-[(2-mercaptomethyl-3-phenylpropionyl)amino]-5-methylbenzoic acid.
Claim 7
Dependent Claim
13 words
The process of claim 1 for the production of the compound 3-[(2-acetylthiomethyl-3-phenylpropionyl)amino]-2-methylbenzoic acid.
Claim 8
Dependent Claim
13 words
The process of claim 1 for the production of the compound 3-[(2-mercaptomethyl-3-phenylpropionyl)amino]-2-methylbenzoic acid.
Claim 9
Dependent Claim
13 words
The process of claim 1 for the production of the compound 3-[(2-acetylthiomethyl-3-phenylpropionyl)amino]-5-ethylbenzoic acid.
Claim 10
Dependent Claim
13 words
The process of claim 1 for the production of the compound 3-[(2-mercaptomethyl-3-phenylpropionyl)amino]-5-ethylbenzoic acid.
Claim 11
Dependent Claim
13 words
The process of claim 1 for the production of the compound 3-[(2-acetylthiomethyl-4-methylpentanoyl)amino]-2-methylbenzoic acid.
Claim 12
Dependent Claim
13 words
The process of claim 1 for the production of the compound 3-[(2-acetylthiomethyl-4-methylpentanoyl)amino]-5-methylbenzoic acid.
Claim 13
Dependent Claim
13 words
The process of claim 1 for the production of the compound 3-[(2-mercaptomethyl-4-methylpentanoyl)amino]-benzoic acid.
Claim 14
Dependent Claim
13 words
The process of claim 1 for the production of the compound 3-[(2-mercaptomethyl-4-methylpentanoyl)amino]-2-methylbenzoic acid.
Claim 15
Dependent Claim
105 words
A process for preparing a solid solution of a N-substituted mercaptopropanamide derivative of the formula: wherein R₁ is mercapto or a group convertible into mercapto when cleaved within the biobody, W is hydrogen atom, an alkyl or an aralkyl, R₂ is an aryl which may optionally have substituent(s), a heterocyclic group which may optionally have substituent(s), or an alkyl which may optionally have substituent(s), X is a cycloalkylene, a cycloalkylidene, or a phenylene which may optionally have substituent(s) or may optionally be fused with other ring, and R₃ is carboxyl or a group convertible into carboxyl when cleaved within the biobody, with an amino acid.
Claim 16
Dependent Claim
105 words
A process for preparing a solid solution of a N-substituted mercaptopropanamide derivative of the formula: wherein R₁ is mercapto or a group convertible into mercapto when cleaved within the biobody, W is hydrogen atom, an alkyl or an aralkyl, R₂ is an aryl which may optionally have substituent(s), a heterocyclic group which may optionally have substituent(s), or an alkyl which may optionally have substituent(s), X is a cycloalkylene, a cycloalkylidene, or a phenylene which may optionally have substituent(s) or may optionally be fused with other ring, and R₃ is carboxyl or a group convertible into carboxyl when cleaved within the biobody, with an amino acid.
Claim 17
Dependent Claim
18 words
The process of claim 14 for the production of a solid solution wherein the amino acid is glycine.
Claim 18
Dependent Claim
22 words
The process of claim 14 for the production of a solid solution wherein X is a (C₁-C₄) alkyl-substituted phenylene or unsubstituted phenylene.
Claim 19
Dependent Claim
29 words
The process of claim 14 for the production of a solid solution wherein R₁ is mercapto or acetylthio, W is hydrogen atom, R₂ is phenyl, and R₃ is carboxyl.
Claim 20
Dependent Claim
18 words
The process of claim 14 for the production of the solid solution of 3-[(2-mercaptomethyl-3-phenyl propionyl)amino]benzoic acid with glycine.
Claim 21
Dependent Claim
17 words
The process of claim 14 for the production of the solid solution of 3-[(2-acetylthiomethyl-3-phenylpropionyl)amino]-5-ethylbenzoic acid with glycine.
Claim 22
Dependent Claim
17 words
The process of claim 14 for the production of the solid solution of 3-[(2-mercaptomethyl-3-phenylpropionyl)amino]-2-methylbenzoic acid with glycine.
Claim 23
Dependent Claim
17 words
The process of claim 14 for the production of the solid solution of 3-[(2-mercaptomethyl-3-phenylpropionyl)amino]-5-methylbenzoic acid with glycine.
References Cited (Backward Citations)
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