EP0185319B1
Expired / Lapsed
EP
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Fluoro coumarins as antilymphoedema agents
Assignee: Roche Diagnostics SpA
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Filing: 1985-12-12
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Granted: 1989-09-06
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Expires: 2005-12-12
Abstract
Abstract A compound of the formulawherein hydrogen, fluorine, chlorine or bromine; B is fluorine, or when A is fluorine B may be hydrogen; R is hydrogen, C,-C<sub>e</sub> branched or unbranched alkyl, CH<sub>2</sub>BR, CH<sub>2</sub>Cl or substituted or unsubstituted phenyl; X is hydrogen, chlorine or bromine; one of R<sub>1</sub> and R<sub>2</sub> is hydrogen and the other is hydroxy or C<sub>1</sub>-C<sub>7</sub> branched or unbranched alkoxy unsubstituted or substituted by a dialkyl amino group, or R, and R<sub>2</sub>, taken together with the carbon atom to which they are linked, form the groupC=O: with the proviso that, when R and X are both hydrogenis a C=O group, and B is fluorine and A is hydrogen is useful as antilimphoedema agent.
Inventors
- 👤 Carmelo A. Gandolfi
- 👤 Odoardo Tofanetti
- 👤 Silvano Spinelli
- 👤 Piervitto Cipolla
- 👤 Sergio Tognella
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-01 23:21
CPC Classifications
C; C07; C07D; C07D311/00; C07D311/02; C07D311/04; C07D311/06; C07D311/20; A; A61; A61P; A61P29/00; A61P3/00; C07D311/08; C07D311/14; C07D311/16; C07D311/18
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
130 words
A compound of the formula: wherein A is hydrogen, fluorine, chlorine or bromine; B is fluorine, or when A is fluorine B may be hydrogen; R is hydrogen, C 1 ―C 8 branched or unbranched alkyl, CH Z BR, CH 2 CI or phenyl; X is hydrogen, chlorine or bromine; one of R 1 and R 2 is hydrogen and the other is hydroxy or C,-C 7 branched or unbranched alkoxy unsubstituted or substituted by a C 1 ―C 2 dialkylamino group, or R 1 and R 2 , taken together with the carbon atom to which they are linked, form the group >C=O with the proviso that when R=X=H, is a C=O group and one of the groups A, B is fluorine, the other one is different from hydrogen.
Claim 2
Dependent Claim
130 words
A compound of the formula: wherein A is hydrogen, fluorine, chlorine or bromine; B is fluorine, or when A is fluorine B may be hydrogen; R is hydrogen, C 1 ―C 8 branched or unbranched alkyl, CH Z BR, CH 2 CI or phenyl; X is hydrogen, chlorine or bromine; one of R 1 and R 2 is hydrogen and the other is hydroxy or C,-C 7 branched or unbranched alkoxy unsubstituted or substituted by a C 1 ―C 2 dialkylamino group, or R 1 and R 2 , taken together with the carbon atom to which they are linked, form the group >C=O with the proviso that when R=X=H, is a C=O group and one of the groups A, B is fluorine, the other one is different from hydrogen.
Claim 3
Dependent Claim
22 words
A compound according to claim 1 wherein R is ―(CH 2 ) n ―CH 3 or wherein n is 1 to 5.
Claim 4
Dependent Claim
28 words
A compound according to claim 1 or claim 2 wherein one of R 1 and R is C 1-7 branched or unbranched alkyl substituted by dimthylamino or diethylamino.
Claim 5
Dependent Claim
31 words
A compound according to claim 1 selected from the group consisting of: 6-fluoro-4-methyl-2H-1-benzopyran-2-one 6-fluoro-4-ethyl-2H-1-benzopyran-2-one 6-fluoro-3-bromo-2H-1-benzopyran-2-one 6-fluoro-3-chloro-2H-1-benzopyran-2-one 6-fluoro-4-methyl-3-chloro-2H-1-benzopyran-2-one 6-fluoro-4-chloromethyl-3-chloro-2H-1-benzopyran-2-one 6,8-difluoro-2H-1-benzopyran-2-one 6-fluoro-4-phenyl-2H-1-benzopyran-2-one 6-fluoro-4-methyl-3-bromo-2H-1-benzopyran-2-one 6-fluoro-4-bromomethyl-3-bromo-2H-1-benzopyran-2-one 8-fluoro-3-bromo-2H-1-benzopyran-2-one 6-fluoro-2ζ-hydroxy-2H-1-benzopyran 6-fluoro-2ζ-hydroxy-2H-1-benzopyran 6-fluoro-2ζ,-ethoxy-2H-1-benzopyran 6-fluoro-2ζ-(2'-dimethylaminoethoxy)-2H-1-benzopyran 6-fluoro-2ζ-(2'-diethylaminoethoxy)-2H-1-benzopyran 6-fluoro-2ζ-isopropoxy-2H-1-benzopyran 6-fluoro-3-bromo-2ζ-hydroxy-2H-1-benzypyran 6-fluoro-3-bromo-2ζ-methoxy-2H-1-benzypyran
Claim 6
Dependent Claim
112 words
Pharmaceutical or veterinary composition comprising as the active principle at least one compound of the formula I wherein A is hydrogen, fluorine, chlorine or bromine; B is fluorine, or when A is fluorine B may be hydrogen; R is hydrogen, C 1 ―C 8 branched or unbranched alkyl, CH 2 BR, CH 2 CI or X is hydrogen, chlorine or bromine; one of R 1 and R 2 is hydrogen and the other is hydroxy or C l -C 7 branched or unbranched alkoxy unsubstituted or substituted by C2-C7 dialkylamino or R i and R 2 , taken together with the carbon atom to which they are linked, form the group >C=O.
Claim 7
Dependent Claim
112 words
Pharmaceutical or veterinary composition comprising as the active principle at least one compound of the formula I wherein A is hydrogen, fluorine, chlorine or bromine; B is fluorine, or when A is fluorine B may be hydrogen; R is hydrogen, C 1 ―C 8 branched or unbranched alkyl, CH 2 BR, CH 2 CI or X is hydrogen, chlorine or bromine; one of R 1 and R 2 is hydrogen and the other is hydroxy or C l -C 7 branched or unbranched alkoxy unsubstituted or substituted by C2-C7 dialkylamino or R i and R 2 , taken together with the carbon atom to which they are linked, form the group >C=O.
Claim 8
Dependent Claim
15 words
Pharmaceutical composition according to claim 5 wherein the active principle is 6-fluoro or 8-fluoro coumarin.
Claim 9
Dependent Claim
22 words
Pharmaceutical composition according to claim 5 wherein the active principle is a compound according to any one of claims 1 to 4.
Claim 10
Dependent Claim
16 words
Pharmaceutical composition according to any one of claims 5 to 7 having anti-inflammatory and antiedematious activity.
Claim 11
Dependent Claim
70 words
A process for producing a compound of formula wherein: R' is hydrogen, C 1-8 branched or unbranched alkyl, or phenyl, and A and B have the meanings given in claim 1, which process comprises reacting, in the presence of a strong acid, a compound of formula wherein A and B are as defined, with a compound of formula wherein Z is carboxyl, C 1-8 branched or unbranched alkyl or phenyl.
Claim 12
Dependent Claim
59 words
A process for producing a compound of formula wherein R, A and B are as defined in claim 1, which process comprises the steps of reacting a compound of formula 1a as defined in claim 9 with chlorine, bromine or iodine to give a compound of formula wherein X is halogen and thereafter dehydrohalogenating the compound of formula IV.
Claim 13
Dependent Claim
75 words
A process for producing a compound of formula wherein R, A, B, and X are as defined in claim 1 and Ri is hydrogen or C 1-7 branched or unbranched alkyl optionally substituted with C 1 ―C 2 dialkylamino, comprising reducing the compound Ib of claim 10 by treatment with an alcohol of formula R 3 0H, wherein R 3 is a C 1 ―C 5 alkyl, optionally substituted with C l -C 2 dialkylamino.
Claim 14
Dependent Claim
49 words
A process for producing a compound of formula 1c as defined in claim 11 comprising treating a compound of formula wherein Ri is hydrogen, with an alcohol wherein R 3 is C 1-5 alkyl optionally substituted with C 1 ―C 2 dialkylamino and dehydrohalogenating the resultant acetal ether derivate.
Claim 15
Dependent Claim
27 words
A process for producing a compound of formula 1 b as defined in claim 11 comprising oxidising a compound of formula 1c as defined in claim 11.
Claim 16
Dependent Claim
31 words
A process as claimed in any one of claims 9 to 13 wherein R is ―(CH 2 ) n ―CH 3 or wherein n is an integer from 1 to 5.
Claim 17
Dependent Claim
35 words
The use of compounds of formula I wherein R, A, B, X, R 1 and R 2 have the meanings of claim 1, for the preparation of pharmaceutical compositions for treating inflammatory and edematous conditions.
Claim 18
Dependent Claim
19 words
The use of 6-fluoro or 8-fluoro coumarin for the preparation of pharmaceutical compositions for treating inflammatory and edematous conditions.
Claim 19
Dependent Claim
19 words
The use of 6-fluoro or 8-fluoro coumarin for the preparation of pharmaceutical compositions for treating inflammatory and edematous conditions.
References Cited (Backward Citations)
No citation records indexed.
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