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US5128338A Expired / Lapsed US ⏱️ 0.0 years remaining

Imidazo [1,2-c] quinazoline compounds

Assignee: Institut Servier de Medecine Translationnelle SARL
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Filing: 1991-03-08
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Granted: 1992-07-07
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Expires: 2011-03-08
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Abstract

Abstract New imidazo [1,2-c] quinazoline compounds useful as coronary smooth muscle relaxants and corresponding to the formula: ##STR1## in which: Y is oxygen or sulfur; R 1 is (C 1 -C 6 ) alkyl optionally substituted by a phenyl itself optionally substituted, a (C 3 -C 6 ) cycloalkyl, optionally substituted phenyl, furyl, thienyl or acyl; R 2 is hydrogen, a halogen or a (C 1 -C 6 ) alkyl optionally substituted by amino or dialkylamino; R 3 is hydrogen, (C 1 -C 6 ) alkyl optionally substituted by an aryl, or R--CO--(CH 2 ) n -- [n being 1, 2 or 3, and R being (C 1 -C 6 ) alkoxy, amino, (alkyl or dialkyl)amino, morpholino or methylpiperazinyl]; and X is hydrogen or a halogen. These compounds and their physiologically tolerated salts can be used in medical treatment of coronary smooth-muscle dysfunctions.

Inventors

  • 👤 Jean-Jacques Bourguignon
  • 👤 Camille-Georges Wermuth
  • 👤 de la Faverie Renaud
  • 👤 Catherine Thollon
  • 👤 Alain Lombet

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-29 09:32
CPC Classifications
C; C07; C07D; C07D487/00; C07D487/02; C07D487/04; A; A61; A61P; A61P11/00; A61P25/00; A61P25/20; A61P25/24; A61P25/26; A61P9/00; A61P9/08; A61P9/10; A61P9/12

Claims Analysis

Total Claims: 11
Claim 1
Independent Claim 318 words
A compound selected from imidazo[1,2-c]quinazolines of the formula I: ##STR25## in which: Y represents oxygen or sulfur; R 1 represents: a) alkyl having 1 to 6 carbon atoms, optionally substituted by phenyl optionally mono- or disubstituted by halogen or alkyl or alkoxy having 1 to 6 carbon atoms; b) mono-, bi- or tricyclic cycloalkyl having 3 to 10 carbon atoms; c) an aromatic group chosen from among: phenyl and phenyl mono- or disubstituted by halogen or alkyl or alkoxy having 1 to 6 carbon atoms, and furyl and thienyl, or d) alkoxycarbonyl, aminocarbonyl or N,N-dialkylaminocarbonyl, in which alkyl has 1 to 6 carbon atoms, or benzoyl optionally mono- or disubstituted by halogen atom or alkyl or alkoxy having 1 to 6 carbon atoms; R 2 represents hydrogen or halogen or alkyl having 1 to 6 carbon atoms optionally substituted by amino, alkylamino or dialkylamino in which alkyl has 1 to 6 carbon atoms; R 3 represents: a) hydrogen, b) alkyl radical having 1 to 6 carbon atoms, optionally substituted by phenyl optionally mono- or polysubstituted by alkyl or alkoxy having 1 to 6 carbon atoms, or c) a radical of formula: R--CO--A-- in which: A is alkylene having 1 to 6 carbon atoms, and R is alkoxy having 1 to 6 carbon atoms or an amino radical of formula: ##STR26## in which R' and R", identical or different, each represent hydrogen or alkyl having 1 to 6 carbon atoms optionally substituted by hydroxyl or alkoxy having 1 to 6 carbon atoms, or R' and R" form, together with the nitrogen atom to which they are attached, a saturated 5 or 6 membered heterocyclic radical optionally containing a second hetero atom selected from oxygen and nitrogen, remaining ring atoms being carbon, d) phenyl, optionally substituted by one or more alkyl or alkoxy having 1 to 6 carbon atoms; X represents hydrogen or halogen, and pharmacologically-acceptable acid addition salts thereof.
Claim 2
Dependent Claim 318 words
A compound selected from imidazo[1,2-c]quinazolines of the formula I: ##STR25## in which: Y represents oxygen or sulfur; R 1 represents: a) alkyl having 1 to 6 carbon atoms, optionally substituted by phenyl optionally mono- or disubstituted by halogen or alkyl or alkoxy having 1 to 6 carbon atoms; b) mono-, bi- or tricyclic cycloalkyl having 3 to 10 carbon atoms; c) an aromatic group chosen from among: phenyl and phenyl mono- or disubstituted by halogen or alkyl or alkoxy having 1 to 6 carbon atoms, and furyl and thienyl, or d) alkoxycarbonyl, aminocarbonyl or N,N-dialkylaminocarbonyl, in which alkyl has 1 to 6 carbon atoms, or benzoyl optionally mono- or disubstituted by halogen atom or alkyl or alkoxy having 1 to 6 carbon atoms; R 2 represents hydrogen or halogen or alkyl having 1 to 6 carbon atoms optionally substituted by amino, alkylamino or dialkylamino in which alkyl has 1 to 6 carbon atoms; R 3 represents: a) hydrogen, b) alkyl radical having 1 to 6 carbon atoms, optionally substituted by phenyl optionally mono- or polysubstituted by alkyl or alkoxy having 1 to 6 carbon atoms, or c) a radical of formula: R--CO--A-- in which: A is alkylene having 1 to 6 carbon atoms, and R is alkoxy having 1 to 6 carbon atoms or an amino radical of formula: ##STR26## in which R' and R", identical or different, each represent hydrogen or alkyl having 1 to 6 carbon atoms optionally substituted by hydroxyl or alkoxy having 1 to 6 carbon atoms, or R' and R" form, together with the nitrogen atom to which they are attached, a saturated 5 or 6 membered heterocyclic radical optionally containing a second hetero atom selected from oxygen and nitrogen, remaining ring atoms being carbon, d) phenyl, optionally substituted by one or more alkyl or alkoxy having 1 to 6 carbon atoms; X represents hydrogen or halogen, and pharmacologically-acceptable acid addition salts thereof.
Claim 3
Dependent Claim 14 words
A physiologically tolerated salt of a compound of claim 1 with a pharmacologically-acceptable acid.
Claim 4
Dependent Claim 7 words
Compound of claim 1 being 2-Ethoxycarbonyl-6-benzyl-5-oxo-5,6-dihydroimidazo[ 1,2-c]quinazoline.
Claim 5
Dependent Claim 6 words
Compound of claim 1 being 2-Phenyl-6-N,N-diethylaminocarbonylmethyl-5-oxo-5,6-dihydroimidazo[1,2-c]quinazoline.
Claim 6
Dependent Claim 6 words
Compound of claim 1 being 2-(p-Methoxyphenyl)-6-N,N-diethylaminocarbonylmethyl-5-oxo-5,6-dihydroimidazo[1,2-c]quinazoline.
Claim 7
Dependent Claim 6 words
Compound of claim 1 being 2-Phenyl-6-(N-methyl-N-phenylacetamido)-5-oxo-5,6-dihydroimidazo[1,2-c]quinazoline.
Claim 8
Dependent Claim 6 words
Compound of claim 1 being 2-Phenyl-6-N,N-dipropylaminocarbonylmethyl-5-oxo-5,6-dihydroimidazo[1,2-c]quinazoline.
Claim 9
Dependent Claim 6 words
Compound of claim 1 being 2-(m-Chlorophenyl)-3-methyl-6-N,N-dipropylaminocarbonylmethyl-5-oxo-5,6-dihydroimidazo[1,2-c]quinazoline.
Claim 10
Dependent Claim 25 words
A pharmaceutical composition useful for treating coronary smooth-muscle dysfunction containing as active principle a compound as claimed in claim 1 together with a pharmaceutically-acceptable carrier.
Claim 11
Dependent Claim 41 words
A method for treating a living animal afflicted with a coronary smooth muscle dysfunction, comprising the step of administering to the said living animal an amount of a compound of claim 1 which is effective for alleviation of the said conditions.

References Cited (Backward Citations)

US4110452A Cited
EP0053767A1 Cited
US4585772A Cited
US4713383A Cited
US4902686A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1995-07-07 1996-01-06 1996-07-07 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1999-07-07 2000-01-06 2000-07-07 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2003-07-07 2004-01-06 2004-07-07 $7700.00 Window Closed / Lapsed

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