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Amino-acid derivatives, their preparation and their use as pharmaceuticals

Assignee: Sankyo Co Ltd
•
Filing: 1984-04-09
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Granted: 1985-10-08
•
Expires: 2004-04-09
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Abstract

Abstract New compounds useful as immunoregulatory and antineoplastic agents are amino-acid derivatives of formula: ##STR1## wherein: n is an integer from 1 to 5; R 1 is a hydrogen atom, an alkyl group, a haloalkyl group, a halogen atom, a mercapto group, an alkylmercapto group, a hydroxy group, an alkoxy group, an acyloxy group, a carboxyl group, an alkoxycarbonyl group, an amino group, an alkyl-substituted amino group, an aryl-substituted amino group, an acylamino group, a haloalkoxycarbonylamino group, an alkanesulphonyl group, a nitro group or a cyano group (and, when n is an integer from 2 to 5, the radicals R 1 may be the same or different); R 2 and R 3 may be the same or different and each is a hydrogen atom or an alkyl group; R 4 is a hydrogen atom, an alkyl group, a cyano group, a cyanoalkyl group, a hydroxyalkyl group, an alkoxycarbonyl group, a carboxyl group, an aryl group, an aralkyl group, a mercaptoalkyl group, an alkylthioalkyl group, or a thioalkyl group (the free bond of the sulphur in said thioalkyl group being joined to the sulphur of another moiety of the same formula); and A is a hydroxy group, an alkoxy group, an amino group, an alkyl-substituted amino group (optionally halogen- or carbamoyl- substituted in the alkyl moiety), a hydrazino group, an alkyl- or aryl- substituted hydrazino group, a hydroxylamino group, an alkoxyamino group or an aralkyloxyamino group; and the pharmaceutically acceptable salts thereof.

Inventors

  • 👤 Mitsuo Nagano
  • 👤 Koichi Hirai
  • 👤 Kouichi Kitamura
  • 👤 Kenkichi Shinkai
  • 👤 Hiroshi Yasuda

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-09 23:02
CPC Classifications
C; C07; C07C; C07C255/00; A; A61; A61P; A61P35/00; A61P37/00; A61P37/02; A61P37/04

Claims Analysis

Total Claims: 17
Claim 1
Independent Claim 68 words
Compounds having the formula ##STR19## wherein R 1 is a halogen atom; R 2 and R 3 are both hydrogen atoms; R 4 is an alkyl group having from 1 to 4 carbon atoms; A is a hydroxy group or an alkoxy group having from 1 to 4 carbon atoms; and n is 1; and, when A is the hydroxy group, the pharmaceutically acceptable carboxylic acid salts thereof.
Claim 2
Dependent Claim 68 words
Compounds having the formula ##STR19## wherein R 1 is a halogen atom; R 2 and R 3 are both hydrogen atoms; R 4 is an alkyl group having from 1 to 4 carbon atoms; A is a hydroxy group or an alkoxy group having from 1 to 4 carbon atoms; and n is 1; and, when A is the hydroxy group, the pharmaceutically acceptable carboxylic acid salts thereof.
Claim 3
Dependent Claim 56 words
Compounds as claimed in claim 1, wherein: R 1 is a chlorine atom; R 2 and R 3 are both hydrogen atoms; R 4 is a methyl group; A is a hydroxy group or an alkoxy group having from 1 to 4 carbon atoms; and n is 1; and the sodium, potassium and calcium salts thereof.
Claim 4
Dependent Claim 39 words
Compounds as claimed in claim 1, selected from the group consisting of: N-(p-Chlorobenzoyl)-2-(2-cyanoethyl)alanine methyl ester; N-(p-chlorobenzoyl)-2-(2-cyanoethyl)alanine; N-(p-Chlorobenzoyl)-2-(2-cyanoethyl)leucine methyl ester; N-(m-Chlorobenzoyl)-2-(2-cyanoethyl)alanine methyl ester; N-(m-Chlorobenzoyl)-2-(2-cyanoethyl)alanine; N-(o-Chlorobenzoyl)-2-(2-cyanoethyl)alanine methyl ester; N-(o-Chlorobenzoyl)-2-(2-cyanoethyl)alanine; 2-(2-Cyanoethyl)-N-(p-fluorobenzoyl)alanine methyl ester; 2-(2-Cyanoethyl)-N-(p-fluorobenzoyl)alanine; 2-(2-Cyanoethyl)-N-(p-bromobenzoyl)alanine methyl ester; 2-(2-Cyanoethyl)-N-(p-bromobenzoyl)alanine; 2-(2-Cyanoethyl)-N-(p-iodobenzoyl)alanine methyl ester; 2-(2-Cyanoethyl)-N-(p-iodobenzoyl)alanine.
Claim 5
Dependent Claim 8 words
The compound of claim 1 which is N-(p-chlorobenzoyl)-2-(2-cyanoethyl)alanine.
Claim 6
Dependent Claim 10 words
The compound of claim 1 which is N-(p-chlorobenzoyl)-2-(2-cyanoethyl)alanine methyl ester.
Claim 7
Dependent Claim 10 words
The compound of claim 1 which is N-(o-chlorobenzoyl)-2-(2-cyanoethyl)alanine methyl ester.
Claim 8
Dependent Claim 10 words
The compound of claim 1 which is N-(p-chlorobenzoyl)-2-(2-cyanoethyl)leucine methyl ester.
Claim 9
Dependent Claim 10 words
The compound of claim 1 which is N-(m-chlorobenzoyl)-2-(2-cyanoethyl)alanine methyl ester.
Claim 10
Dependent Claim 8 words
The compound of claim 1 which is N-(m-chlorobenzoyl)-2-(2-cyanoethyl)alanine.
Claim 11
Dependent Claim 8 words
The compound of claim 1 which is N-(o-chlorobenzoyl)-2-(2-cyanoethyl)alanine.
Claim 12
Dependent Claim 10 words
The compound of claim 1 which is 2-(2-cyanoethyl)-N-(p-fluorobenzoyl)alanine methyl ester.
Claim 13
Dependent Claim 8 words
The compound of claim 1 which is 2-(2-cyanoethyl)-N-(p-fluorobenzoyl)alanine.
Claim 14
Dependent Claim 10 words
The compound of claim 1 which is 2-(2-cyanoethyl)-N-(p-bromobenzoyl)alanine methyl ester.
Claim 15
Dependent Claim 8 words
The compound of claim 1 which is 2-(2-cyanoethyl)-N-(p-bromobenzoyl)alanine.
Claim 16
Dependent Claim 10 words
The compound of claim 1 which is 2-(2-cyanoethyl)-N-(p-iodobenzoyl)alanine methyl ester.
Claim 17
Dependent Claim 8 words
The compound of claim 1 which is 2-(2-cyanoethyl)-N-(p-iodobenzoyl)alanine.

References Cited (Backward Citations)

US3125583A Cited
US2847451A Cited
US2891053A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1988-10-07 1989-04-08 1989-10-08 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1992-10-07 1993-04-08 1993-10-08 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1996-10-07 1997-04-08 1997-10-08 $7700.00 Window Closed / Lapsed

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