US4670439A
Expired / Lapsed
US
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2H-1-benzopyran-2-one derivatives, processes for the preparation thereof and pharmaceutical compositions containing them
Assignee: Roche Diagnostics GmbH
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Filing: 1985-07-16
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Granted: 1987-06-02
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Expires: 2005-07-16
Abstract
Abstract The present invention provides 2H-1-benzopyran-2-one derivatives of the general formula: <IMAGE> (I) wherein either R1 is a lower alkyl radical, optionally substituted by phenyl, which can be substituted by lower alkyl, lower alkoxy, hydroxyl or halogen, and R2 is trifluoromethyl, cyano, hydroxymethyl, alkoxymethyl, acyloxymethyl, halogenomethyl, aminomethyl, mono- or dialkylaminomethyl, acyl, carboxyl, alkoxycarbonyl or carbamoyl, which can be mono- or disubstituted by lower alkyl; or R1 is trifluoromethyl, cyano, hydroxymethyl, alkoxymethyl, acyloxymethyl, halogenomethyl, aminomethyl, mono- or dialkylaminomethyl, acyl, carboxyl, alkoxycarbonyl or carbamoyl, which can be mono- or disubstituted by lower alkyl, and R2 is a lower alkyl radical, optionally substituted by phenyl, which can be substituted by lower alkyl, lower alkoxy, hydroxyl or halogen, and R3 is a phenyl or benzyl radical which can be substituted by lower alkyl, lower alkoxy, hydroxyl or halogen; and the pharmacologically acceptable salts thereof. The present invention also provides processes for the preparation of these 2H-1-benzopyran-2-one derivatives and pharmaceutical compositions containing them.
Inventors
- 👤 Ernst-Christian Witte
- 👤 Peter Neubert
- 👤 Androniki Roesch
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 16:28
CPC Classifications
C; C07; C07D; C07D311/00; C07D311/02; C07D311/04; C07D311/06; C07D311/08; C07D311/18; A; A61; A61P; A61P37/00; A61P37/08; C07D311/16; C07D311/42; C07D311/44; C07D311/54
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
218 words
A 2H-1-Benzopyran-2-one compound of the formula: ##STR11## wherein R 1 is C 1 -C 6 alkyl or C 1 -C 6 alkyl substituted by phenyl or phenyl substituted by C 1 -C 6 alkyl, C 1 -C 6 alkoxy, hydroxyl, fluorine, chlorine or bromine and R 2 is trifluoromethyl, cyano, hydroxymethyl, C 1 -C 6 alkoxymethyl, C 1 -C 6 acyloxymethyl, halomethyl, aminomethyl, mono- or dialkylaminomethyl wherein each alkyl has 1-6 carbon atoms, C 1 -C 6 acyl, carboxyl, C 1 -C 6 alkoxycarbonyl or carbamoyl, which can be mono- or disubstituted by C 1 -C 6 alkyl; or R 1 is trifluoromethyl, cyano, hydroxymethyl, C 1 -C 6 alkoxymethyl, acyloxymethyl, halomethyl, aminomethyl, mono- or dialkylaminomethyl wherein each alkyl has 1-6 carbon atoms, C 1 -C 6 acyl, carboxyl, C 1 -C 6 alkoxycarbonyl or carbamoyl, which can be mono- or disubstituted by C 1 -C 6 alkyl, and R 2 is a C 1 -C 6 alkyl or C 1 -C 6 alkyl substituted by phenyl or phenyl substituted by C 1 -C 6 alkyl, C 1 -C 6 alkoxy, hydroxyl, fluorine, chlorine or bromine and R 3 is phenyl, benzyl, or phenyl or benzyl substituted by C 1 -C 6 alkyl, C 1 -C 6 alkoxy, hydroxyl,fluorine, chlorine, or bromine; and the pharmacologically acceptable salts thereof.
Claim 2
Dependent Claim
218 words
A 2H-1-Benzopyran-2-one compound of the formula: ##STR11## wherein R 1 is C 1 -C 6 alkyl or C 1 -C 6 alkyl substituted by phenyl or phenyl substituted by C 1 -C 6 alkyl, C 1 -C 6 alkoxy, hydroxyl, fluorine, chlorine or bromine and R 2 is trifluoromethyl, cyano, hydroxymethyl, C 1 -C 6 alkoxymethyl, C 1 -C 6 acyloxymethyl, halomethyl, aminomethyl, mono- or dialkylaminomethyl wherein each alkyl has 1-6 carbon atoms, C 1 -C 6 acyl, carboxyl, C 1 -C 6 alkoxycarbonyl or carbamoyl, which can be mono- or disubstituted by C 1 -C 6 alkyl; or R 1 is trifluoromethyl, cyano, hydroxymethyl, C 1 -C 6 alkoxymethyl, acyloxymethyl, halomethyl, aminomethyl, mono- or dialkylaminomethyl wherein each alkyl has 1-6 carbon atoms, C 1 -C 6 acyl, carboxyl, C 1 -C 6 alkoxycarbonyl or carbamoyl, which can be mono- or disubstituted by C 1 -C 6 alkyl, and R 2 is a C 1 -C 6 alkyl or C 1 -C 6 alkyl substituted by phenyl or phenyl substituted by C 1 -C 6 alkyl, C 1 -C 6 alkoxy, hydroxyl, fluorine, chlorine or bromine and R 3 is phenyl, benzyl, or phenyl or benzyl substituted by C 1 -C 6 alkyl, C 1 -C 6 alkoxy, hydroxyl,fluorine, chlorine, or bromine; and the pharmacologically acceptable salts thereof.
Claim 3
Dependent Claim
96 words
The compound of claim 1 wherein R 1 is C 1 -C 6 alkyl or C 1 -C 6 alkyl substituted by phenyl or phenyl substituted by C 1 -C 6 alkyl, C 1 -C 6 alkoxy, hydroxyl, fluorine, chlorine or bromine and R 2 is trifluoromethyl, cyano, hydroxymethyl, C 1 -C 6 alkoxymethyl, C 1 -C 6 acyloxymethyl, halomethyl, aminomethyl, mono- or dialkylaminomethyl wherein each alkyl has 1-6 carbon atoms, C 1 -C 6 acyl, carboxyl, C 1 -C 6 alkoxycarbonyl or carbamoyl, which can be mono- or disubstituted by C 1 -C 6 alkyl.
Claim 4
Dependent Claim
92 words
The compound of claim 1 wherein R 1 is trifluoromethyl, cyano, hydroxymethyl, C 1 -C 6 alkoxymethyl, acyloxymethyl, halomethyl, aminomethyl, mono-or dialkylaminomethyl wherein each alkyl has 1-6 carbon atoms, C 1 -C 6 acyl, carboxyl, C 1 -C 6 alkoxycarbonyl or carbamoyl, which can be mono- or disubstituted by C 1 -C 6 alkyl, and R 2 is a C 1 -C 6 alkyl or C 1 -C 6 alkyl substituted by phenyl or phenyl substituted by C 1 -C 6 alkyl, C 1 -C 6 alkoxy, hydroxyl, fluorine, chlorine or bromine.
Claim 5
Dependent Claim
36 words
The compound of claim 1 wherein each said alkyl is individually selected from the group consisting of methyl or ethyl and each said alkoxy group is individually selected from the group consisting of methoxy or ethoxy.
Claim 6
Dependent Claim
41 words
The compound of claim 1 wherein R 1 is C 1 -C 6 alkyl or C 1 -C 6 alkyl substituted with phenyl, R 2 is trifluoromethyl, cyano, hydroxymethyl,C 1 -C 6 alkoxymethyl, carboxyl or N, N'-C 1 -C 6 -dialkyl-carbamoyl.
Claim 7
Dependent Claim
14 words
The compound of claim 1 wherein each said acyloxymethyl is benzoyloxymethyl, pivaloyloxymethyl or acetoxymethyl.
Claim 8
Dependent Claim
10 words
The compound of claim 1 designated 7-{3- {4-[(4-chlorophenyl)-methyl]-1-piperazinyl}- propoxy}-4-methyl-2H-1-benzopyran-2-one-3-carboxylic acid.
Claim 9
Dependent Claim
7 words
The compound of claim 1 designated 7-{3-{4-[(4-chlorophenyl)-methyl]-1-piperazinyl}-propoxy}-4-hydroxymethyl-3-methyl-2H-1-benzopyran-2-one.
Claim 10
Dependent Claim
10 words
The compound of claim 1 designated 7-{3-{4-[(4-chlorophenyl)methyl 9 -1-piperazinyl}-propoxy}-3-cyano-4-methyl -2H-1-benzopyran-2-one.
Claim 11
Dependent Claim
9 words
The compound of claim 1 designated 7-{3-{4-[(4-chlorophenyl)-methyl]-1-piperazinyl}-propoxy}-4-methyl-2H-1-benzopyran-2-one-3-carboxylic acid diethylamide.
Claim 12
Dependent Claim
8 words
The compound of claim 1 designated 7-{3- {4-[(4-chlorophenyl)-methyl]-1-piperazinyl}-propoxy}-3-hydroxymethyl-4-methyl-2H-1-benzopyran-2-one.
Claim 13
Dependent Claim
30 words
A pharmaceutical composition comprising a therapeutically effective amount, for inhibiting allergic reactions of the skin and bronchi and inflammations, of the compound of claim 1 in a pharmaceutically acceptable carrier.
Claim 14
Dependent Claim
21 words
The pharmaceutical composition of claim 12 comprising 10 to 300 mg of said compound in a carrier suitable for oral ingestion.
Claim 15
Dependent Claim
20 words
The pharmaceutical composition of claim 12 comprising 0.05 to 50 mg/ml of said compound in a carrier suitable for injection.
Claim 16
Dependent Claim
38 words
A pharmaceutical composition comprising a therapeutically effective amount, for inhibiting allergic reactions of the skin and bronchi and inflammations, of thecompound of claim 1 designated 7-{3-{4-[(4-chlorophenyl)-methyl]-1-piperazinyl}-propoxy}-4-hydroxymethyl-3-methyl-2H-1-benzopyran-2-one 7-{3-{4-[(4-chlorophenyl)-methyl]-1-piperazinyl}-propoxy}-3-cyano-4-methyl-2H-1-benzopyran-2-one 7-{3-{4-[(4-chlorophenyl)-methyl]-1-piperazinyl}-propoxy}-4-methyl-2H-1-benzopyran-2-one-3-carboxylic acid diethylamide. 7-{3-{4-[(4-chlorophenyl)-methyl]-1-piperazinyl}-propoxy}-3-hydroxymethyl-4-methyl-2H-1-benzopyran-2-one 7-{3-{4-[(4-chlorophenyl)-methyl)]-1-piperazinyl}-propoxy}-4-methyl-2H-1-benzopyran-2-one-3-carboxylic acid in a pharmaceutically effective carrier.
Claim 17
Dependent Claim
26 words
A method of inhibiting allergic reactions of the skin and bronchi comprising administering, orally or by injection, an effective amount of the compound of claim 1.
Claim 18
Dependent Claim
23 words
A method of inhibiting allergic reactions of the skin comprising applying to the skin, an effective amount of the compound of claim 1.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1990-06-01 | 1990-12-01 | 1991-06-02 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-06-01 | 1994-12-01 | 1995-06-02 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-06-01 | 1998-12-01 | 1999-06-02 | $7700.00 | Window Closed / Lapsed |