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US4428955A Expired / Lapsed US ⏱️ 0.0 years remaining

Benzopyran compounds, pharmaceutical compositions containing them and methods of use

Assignee: Roche Diagnostics GmbH
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Filing: 1982-04-27
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Granted: 1984-01-31
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Expires: 2002-04-27
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Abstract

Abstract The present invention provides benzopyranyl ethers of the general formula: <IMAGE> wherein A is an alkylene radical containing 2 to 4 carbon atoms and R is a hydrogen atom or an acyl radical; as well as the salts thereof with pharmacologically acceptable acids. The present invention also provides processes for the preparation of these compounds and pharmaceutical compositions containing them. Furthermore, the present invention is concerned with the use of these compounds for treating allergic diseases.

Inventors

  • 👤 Walter-Gunar Friebe
  • 👤 Wolfgang Kampe
  • 👤 Egon Roesch
  • 👤 Otto-Henning Wilhelms

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-06 17:25
CPC Classifications
C; C07; C07D; C07D405/00; C07D405/02; C07D405/12; A; A61; A61P; A61P37/00; A61P37/08; A61P43/00

Claims Analysis

Total Claims: 18
Claim 1
Independent Claim 166 words
Benzopyranyl ether compound of the formula ##STR5## wherein A is alkylene or 2 to 4 carbons; and R is hydrogen or acyl selected from the group consisting of substituted or unsubstituted alkanoyl radicals containing up to 5 carbon atoms, wherein the substituents are selected from fluorine, chlorine, bromine, phenyl or naphthyl; substituted or unsubstituted lower alkenoyl radicals containing 3 to 6 carbon atoms, wherein the substituents are selected from substituted or unsubstituted phenyl wherein the substituents are selected from hydroxyl, halogen, alkyl containing up to 6 carbon atoms and alkoxy containing up to 6 carbon atoms unsubstituted or substituted benzoyl, or naphthoyl wherein the substituents are fluorine, chlorine, bromine, hydroxyl, lower alkyl, lower alkoxy, lower alkoxycarbonyl, lower alkanoyloxy, carboxyl, nitro, amino, lower alkanoylamino, nitrile, trifluoromethyl, carbamoyl, lower alkylthio, lower alkylsulphinyl, lower alkylsulphonyl, lower alkanoyl, benzoyl, hydroxy lower alkyl or lower alkoxy lower alkyl; furancarbonyl, thiophenecarbonyl, pyridinecarbonyl, tetrahydrofuran-carbonyl, tetrahydrothiophene-carbonyl or C 3 -C 7 cycloalkylcarbonyl; or benzene-sulphonyl or methane sulphonyl, and salts thereof with pharmacologically acceptable acids.
Claim 2
Dependent Claim 166 words
Benzopyranyl ether compound of the formula ##STR5## wherein A is alkylene or 2 to 4 carbons; and R is hydrogen or acyl selected from the group consisting of substituted or unsubstituted alkanoyl radicals containing up to 5 carbon atoms, wherein the substituents are selected from fluorine, chlorine, bromine, phenyl or naphthyl; substituted or unsubstituted lower alkenoyl radicals containing 3 to 6 carbon atoms, wherein the substituents are selected from substituted or unsubstituted phenyl wherein the substituents are selected from hydroxyl, halogen, alkyl containing up to 6 carbon atoms and alkoxy containing up to 6 carbon atoms unsubstituted or substituted benzoyl, or naphthoyl wherein the substituents are fluorine, chlorine, bromine, hydroxyl, lower alkyl, lower alkoxy, lower alkoxycarbonyl, lower alkanoyloxy, carboxyl, nitro, amino, lower alkanoylamino, nitrile, trifluoromethyl, carbamoyl, lower alkylthio, lower alkylsulphinyl, lower alkylsulphonyl, lower alkanoyl, benzoyl, hydroxy lower alkyl or lower alkoxy lower alkyl; furancarbonyl, thiophenecarbonyl, pyridinecarbonyl, tetrahydrofuran-carbonyl, tetrahydrothiophene-carbonyl or C 3 -C 7 cycloalkylcarbonyl; or benzene-sulphonyl or methane sulphonyl, and salts thereof with pharmacologically acceptable acids.
Claim 3
Dependent Claim 12 words
Benzopyranyl ether compound as claimed in claim 1, wherein A is ethylene.
Claim 4
Dependent Claim 12 words
Benzopyranyl ether compound as claimed in claim 1, wherein A is propylene.
Claim 5
Dependent Claim 12 words
Benzopyranyl ether compound as claimed in claim 1, wherein A is butylene.
Claim 6
Dependent Claim 12 words
Benzopyranyl ether compound as claimed in claim 1, wherein R is hydrogen.
Claim 7
Dependent Claim 24 words
Benzopyranyl ether compound as claimed in claim 1 wherein R is benzoyl or benzoyl substituted by fluorine, chlorine, methyl, methoxy, hydroxy, amino or nitro.
Claim 8
Dependent Claim 18 words
Benzopyranyl ether compound as claimed in claim 1, wherein R is alkanoyl with up to 5 carbon atoms.
Claim 9
Dependent Claim 10 words
Benzopyranyl ether compound as claimed in claim 1, designated 7-[3-(4-Benzamidopiperidino)-propoxy]-2-methyl-4H-1-benzopyran-4-one.
Claim 10
Dependent Claim 10 words
Benzopyranyl ether compound as claimed in claim 1, designated 7-{3-[4-(4-fluorobenzamido)-piperidino]-propoxy}-2-methyl-4H-1-benzopyran-4-one.
Claim 11
Dependent Claim 10 words
Benzopyranyl ether compound as claimed in claim 1, designated 7-{3-[4-(2-methylbenzamido)-piperidino]-propoxy}-2-methyl-4H-1-benzopyran-4-one.
Claim 12
Dependent Claim 33 words
Pharmaceutical composition for the treatment of allergic diseases comprising a pharmaceutical acceptable carrier and, in an amount effective to treat allergic diseases, at least one benzopyranyl ether compound as claimed in claim 1.
Claim 13
Dependent Claim 23 words
Pharmaceutical composition as claimed in claim 11, wherein said benzopyranyl ether compound is at least one of the following: 7-[3-(4-Benzamidopiperidino)-propoxy]-2-methyl-4H-benzopyran-4-one; 7-{3-[4-(4-fluorobenzamido)-piperidino]-propoxy}-2-methyl-4H-1-benzopyran-4-one; and 7-{3-[4-(2-methylbenzamido)-piperidino]-propoxy}-2-methyl-4H-1-benzopyran-4-one.
Claim 14
Dependent Claim 26 words
Method of treatment of allergic diseases which comprises applying to an afflicted subject an effective amount of a benzopyranyl ether compound as claimed in claim 1.
Claim 15
Dependent Claim 26 words
Method of treatment of allergic diseases as claimed in claim 13, wherein said benzopyranyll ether is at least one compound selected from 7-[3-(4-Benzamidopiperidino)-propoxy]-2-methyl-4H-benzopyran-4-one; 7-{3-[4-(4-fluorobenzamido)-piperidino]-propoxy}-2-methyl-4H-1-benzopyran-4-one; and 7-{3-[4-(2-methylbenzamido)-piperidino]-propoxy}-2-methyl-4H-1-benzopyran-4-one.
Claim 16
Dependent Claim 33 words
Method of treatment of allergic diseases as claimed in claim 13, wherein said compound is applied in an amount of from 0.1 to 50 mg/kg of body weight of the subject, per day.
Claim 17
Dependent Claim 20 words
Method of treatment of allergic diseases as claimed in claim 15, wherein the applied dosage is 0.5 to 40 mg/kg.
Claim 18
Dependent Claim 20 words
Method of treatment of allergic diseases as claimed in claim 16, wherein the applied dosage is 1 to 20 mg/kg.

References Cited (Backward Citations)

US3046275A Cited
US4330549A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1987-01-30 1987-08-01 1988-01-31 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1991-01-30 1991-08-01 1992-01-31 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1995-01-30 1995-08-01 1996-01-31 $7700.00 Window Closed / Lapsed

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