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EP0186367B1 Expired / Lapsed EP ⏱️ 0.0 years remaining

Acidic indole compounds and their use as antiallergy agents

Assignee: Warner Lambert Co LLC
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Filing: 1985-12-10
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Granted: 1993-03-03
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Expires: 2005-12-10
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Abstract

Abstract There are disclosed compounds having the following general formula (I): <CHEM> and pharmaceutically acceptable salts thereof, wherein: R<1> and Q are each, independently, H, an alkyl having from one to twelve carbon atoms, an alkoxy having from one to twelve carbon atoms, mercapto, an alkylthio having from one to four carbon atoms, an alkylsulphinyl having from one to four carbon atoms, an alkylsulphonyl having from one to four carbon atoms, a hydroxy group, a nitro group, an amino group, substituted amino group or a halogen, R<1> being further chosen from a methylenedioxy radical attached to adjacent carbon atoms of the benzene ring; R<2> is H, an alkyl having from one to twelve carbon atoms, a phenyl radical, a substituted phenyl radical or a benzyl radical; R<3> is H, an alkyl having from one to twelve carbon atoms, an alkoxy having from one to twelve carbon atoms, mercapto, an alkylthio having from one to four carbon atoms, a phenylthio radical, a substituted phenylthio radical, an alkylsulphinyl having from one to four carbon atoms, a phenylsulphinyl radical, a substituted phenylsulphinyl radical, an alkylsulphonyl hving from one to four carbon atoms, a phenylsolphonyl radical, a substituted phenylsolphonyl radical an amino group, or a substituted amino group; and R<4> is <CHEM> <??>Methods of preparing the compounds, compositions comprising the compounds and the pharmaceutical use of the compounds are also disclosed.

Inventors

  • 👤 David T. Connor
  • 👤 Paul C. Unangst
  • 👤 S. Russell Stabler

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-11-01 21:12
CPC Classifications
C; C07; C07D; C07D403/00; C07D403/02; C07D403/04; A; A61; A61P; A61P25/00; A61P25/04; A61P29/00; A61P37/00; A61P37/08; A61P43/00; A61P9/00; C07D209/00; C07D209/02; C07D209/04; C07D209/30; C07D209/42; C07D403/12

Claims Analysis

Total Claims: 13
Claim 1
Independent Claim 277 words
A compound having the following general formula (I) : and pharmaceutically acceptable salts thereof, wherein: R¹ and Q are each, independently, H, an alkyl having from one to twelve carbon atoms, an alkoxy having from one to twelve carbon atoms, mercapto, an alkylthio having from one to four carbon atoms, an alkylsulphinyl having from one to four carbon atoms, an alkylsulphonyl having from one to four carbon atoms, a hydroxy group, a nitro group, an amino group, a substituted amino group or a halogen, R¹ being further chosen from a methylenedioxy radical attached to adjacent carbon atoms of the benzene ring; R² is H, an alkyl having from one to twelve carbon atoms, a phenyl radical, a substituted phenyl radical or a benzyl radical; R³ is H, an alkyl having from one to twelve carbon atoms, an alkoxy having from one to twelve carbon atoms, mercapto, an alkylthio having from one to four carbon atoms, a phenylthio radical, a substituted phenylthio radical, an alkylsulphinyl having from one to four carbon atoms, a phenylsulphinyl radical, a substituted phenylsulphinyl radical, an alkylsulphonyl having from one to four carbon atoms, a phenylsulphonyl radical, a substituted phenylsulphonyl radical, an amino group, or a substituted amino group; and R⁴ is or [wherein substituted phenyl is a phenyl having one or two substituents selected from alkyl of from one to four carbons inclusive, alkoxy of from one to four carbons inclusive, hydroxy, nitro, amino, mono- or di-alkyl amino wherein alkyl is from one to four carbons, mercapto, alkylthio of from one to four carbons, methylenedioxy, or halogen and substituted amino is mono- or di-alkyl amino wherein alkyl is from one to four carbons.]
Claim 2
Dependent Claim 9 words
A compound according to Claim 1, wherein R⁴ is
Claim 3
Dependent Claim 9 words
A compound according to Claim 1, wherein R⁴ is
Claim 4
Dependent Claim 10 words
A compound according to Claim 2, wherein R³ is alkoxy.
Claim 5
Dependent Claim 119 words
A compound according to Claim 4, having one of the following names: 3-methoxy-1-methyl- N -1 H -tetrazol-5-yl-1 H -indole-2-carboxamide; 1-hexyl-3-methoxy- N -1 H- tetrazol-5-yl-1 H -indole-2-carboxamide; 3-methoxy-1-nonyl- N -1 H -tetrazol-5-yl-1H-indole-carboxamide; 3-methoxy-1-(phenylmethyl)- N -1 H -tetrazol-5-yl-1 H -indole-2-carboxamide; 3-methoxy-1-phenyl- N -1 H -tetrazol-5-yl-1 H -indole-2-carboxamide; 3-(1-methylethoxy)-1-phenyl- N -1 H -tetrazol-5-yl-1 H -indole-2-carboxamide; 1-(4-methoxyphenyl)-3-(1-methylethoxy)-N-1 H -tetrazol-5-yl-1 H -indole-2-carboxamide; 5-chloro-3-(1-methylethoxy)-1phenyl- N -1 H -tetrazol-5-yl-1 H -indole-2-carboxamide; 5-methoxy-1-methyl-3(1-methylethoxy)- N -1 H -tetrazol-5-yl-1 H -indole-2-carboxamide; 3,5-dimethoxy-1-phenyl- N -1 H -tetrazol-5-yl-1 H -indole-2-carboxamide; 3-ethoxy-5-methoxy-1-phenyl- N -1 H -tetrazol-5-yl-1 H -indole-2-carboxamide; 5-methoxy-3-(1-methylethoxy)-1-phenyl- N -1 H -tetrazol-5-yl-1 H -indole-2-carboxamide; 3-methoxy- N -1 H -tetrazol-5-yl-1H-indole-2-carboxamide; 3-methoxy-1-nonyl- N -1 H -tetrazol-5-yl-1 H -indole-2-carboxamide; 5-methoxy-3-(n-nonyloxy)-1-phenyl- N -1 H -tetrazol-5-yl-1 H -indole-2-carboxamide; and 3-(n-dodecyloxy)-5-methoxy-1-phenyl- N -1 H -tetrazol-5-yl--1 H -indole-2-carboxamide.
Claim 6
Dependent Claim 49 words
A compound according to Claim 2 having one of the following names: 3-(diethylamino)-5-methoxy-1-phenyl- N -1 H -tetrazol-5-yl-1 H -indole-2-carboxamide; 5-methoxy-3-(methylthio)-1-phenyl- N -1 H -tetrazol-5-yl-1- H -indole-2-carboxamide; 5-methoxy-3-[(1-methylethyl)thio]-1phenyl- N -1 H -tetrazol-5-yl-1 H -indole-2-carboxamide; 5-methoxy-1-phenyl-3(phenylthio)- N -1 H -tetrazol-5-yl-1 H -indole-2-carboxamide; 5-methoxy-3-(methylsulphonyl)-1-phenyl- N -1 H -tetrazol-5-yl-1 H -indole-2-carboxamide; and 5-methoxy-3-[(1-methylethyl)thio]-1-phenylmethyl-N-1H-tetrazol-5-yl-1H-indole-2-carboxamide
Claim 7
Dependent Claim 24 words
A pharmaceutical composition comprising an effective amount of a compound according to any preceding claim in admixture with a pharmaceutically acceptable carrier or diluent.
Claim 8
Dependent Claim 31 words
For use in a method of treating allergies in mammals, a compound as claimed in any one of Claims 1 to 6 or a pharmaceutical composition as claimed in Claim 7.
Claim 9
Dependent Claim 53 words
A process for the preparation of a compound of formula I as defined in Claim wherein R⁴ is A, which comprises reacting a compound of the Formula (III) wherein R¹, Q, R², and R³ are as defined in Claim 1 with a compound of Formula (II) in the presence of a coupling agent.
Claim 10
Dependent Claim 49 words
A process for the preparation of a compound of formula I as defined in Claim 1 wherein R⁴ is B which comprises treating a compound of Formula (IV) wherein R¹, Q, R², and R³ are as defined in Claim 1 above by a known method or a variant thereof.
Claim 11
Dependent Claim 13 words
5-Methoxy-3-(1-methylethoxy)-1-phenyl- N -1 H -tetrazol-5-yl-1 H -indole-2-carboxamide, or its L-arginate or sodium salt.
Claim 12
Dependent Claim 7 words
5-Methoxy-1-phenyl-3-(phenylmethoxy)- N -1 H -tetrazol-5-yl-1-1 H -indole-2-carboxamide.
Claim 13
Dependent Claim 7 words
1-Phenyl-3(phenylmethoxy)- N -1 H -tetrazol-5-yl-1 H -indole-2-carboxamide.

References Cited (Backward Citations)

US4316904A Cited
US4432986A Cited
EP0146243A1 Cited
EP0187487A1 Cited

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