US4428955A
Expired / Lapsed
US
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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
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 |