2-Hydroxy-5-phenylazobenzoic acid derivatives and method of treating ulcerative colitis therewith
First Claim
1. 2-Hydroxy-5-phenylazobenzoic acid derivatives of the general formula:
- ##STR6## wherein X is an --SO2 -- or --CO-- group and R is either a phenyl or carboxymethylphenyl radical or is a radical of the formula --(CH2)n --Y, in which Y is a hydroxyl group, an amino group, a monoalkyl- or dialkyl-amino group, the alkyl moieties of which contain up to 6 carbon atoms or a carboxylic or sulphonic acid group and n is a whole number of from 1 to 6 and in which one or more of the hydrogen atoms in the alkylene radical can be replaced by amino groups, monoalkyl- or dialkyl-amino groups, the alkyl moieties of which contain up to 6 carbon atoms or alkyl radicals and in which the --(CH2)n --Y radical is either attached directly to the nitrogen atom or via a benzene ring, with the proviso that R--NH--X-- is other than a --CO--NH--CH2 --COOH radical; and
the esters and non-toxic, pharmacologically acceptable salts thereof.
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Accused Products
Abstract
The present invention provides a pharmaceutical composition for treating ulcerative colitis containing at least one compound of the general formula: ##STR1## wherein X is an --SO2 -- or --CO-- group and R is either an unsubstituted or substituted non-heterocyclic aromatic ring system or is a radical of the general formula --(CH2)n --Y, in which Y is a hydroxyl group, an unsubstituted or substituted amino group or a carboxylic or sulphonic acid group and n is a whole number of from 1 to 6 and in which one or more hydrogen atoms in the alkylene radical can be replaced by unsubstituted or substituted amino groups or alkyl radicals and in which the --(CH2)n --Y radical is either attached directly to the nitrogen atom or via a benzene ring; and/or containing at least one ester thereof and/or at least one non-toxic, pharmaceutically acceptable salt thereof, in admixture with a solid or liquid pharmaceutical diluent or carrier. Furthermore, the present invention provides a process for preparing the compounds of the above-given general formulae and also provides a method of treating ulcerative colitis.
99 Citations
13 Claims
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1. 2-Hydroxy-5-phenylazobenzoic acid derivatives of the general formula:
- ##STR6## wherein X is an --SO2 -- or --CO-- group and R is either a phenyl or carboxymethylphenyl radical or is a radical of the formula --(CH2)n --Y, in which Y is a hydroxyl group, an amino group, a monoalkyl- or dialkyl-amino group, the alkyl moieties of which contain up to 6 carbon atoms or a carboxylic or sulphonic acid group and n is a whole number of from 1 to 6 and in which one or more of the hydrogen atoms in the alkylene radical can be replaced by amino groups, monoalkyl- or dialkyl-amino groups, the alkyl moieties of which contain up to 6 carbon atoms or alkyl radicals and in which the --(CH2)n --Y radical is either attached directly to the nitrogen atom or via a benzene ring, with the proviso that R--NH--X-- is other than a --CO--NH--CH2 --COOH radical; and
the esters and non-toxic, pharmacologically acceptable salts thereof.
- ##STR6## wherein X is an --SO2 -- or --CO-- group and R is either a phenyl or carboxymethylphenyl radical or is a radical of the formula --(CH2)n --Y, in which Y is a hydroxyl group, an amino group, a monoalkyl- or dialkyl-amino group, the alkyl moieties of which contain up to 6 carbon atoms or a carboxylic or sulphonic acid group and n is a whole number of from 1 to 6 and in which one or more of the hydrogen atoms in the alkylene radical can be replaced by amino groups, monoalkyl- or dialkyl-amino groups, the alkyl moieties of which contain up to 6 carbon atoms or alkyl radicals and in which the --(CH2)n --Y radical is either attached directly to the nitrogen atom or via a benzene ring, with the proviso that R--NH--X-- is other than a --CO--NH--CH2 --COOH radical; and
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2. 5-(4-Phenylsulphamoylphenylazo)-salicylic acid and the sodium salt thereof.
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3. Disodium salt of 5-(4-carboxymethylcarbamoylphenylazo)-salicylic acid.
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4. 5-(Carboxyethylcarbamoyl-4-phenylazo)-salicylic acid and the disodium salt thereof.
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5. 5-(Sulphoethylcarbamoyl-4-phenylazo)-salicylic acid.
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6. 5-(4-Hydroxyethylcarbamoylphenylazo)-salicylic acid and the sodium salt thereof.
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7. 5-(α
- -Methylcarboxymethylcarbamoyl-4-phenylazo)-salicylic acid.
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8. 5-[(4-Carboxymethylphenyl)-sulphamoyl-4-phenylazo]-salicylic acid.
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9. 5-(Carboxypentylcarbamoyl-4-phenylazo)-salicylic acid.
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10. 5-(α
- -Dimethylaminocarboxypentylcarbamoyl-4-phenylazo)-salicylic acid and the disodium salt thereof.
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11. 5-(Diethylaminoethylcarbamoyl-4-phenylazo)-salicylic acid.
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12. A pharmaceutical composition for the treatment of ulcerative colitis in humans, containing an effective amount to treat ulcerative colitis, of at least one compound of the formula:
- ##STR7## wherein X is an --SO2 -- or --CO-- group and R is either phenyl or carboxymethylphenyl radical or is a radical of the general formula --(CH2)n --Y, in which Y is a hydroxyl group, an amino group or a monoalkyl- or dialkyl-amino group, the alkyl moieties of which contain up to 6 carbon atoms or a carboxylic or sulphonic acid group and n is a whole number of from 1 to 6 and in which one or more hydrogen atoms in the alkylene radical can be replaced by amino groups, monoalkyl- or dialkyl-amino groups, the alkyl moieties of which contain up to 6 carbon atoms or alkyl radicals and in which the --(CH2)n --Y radical is either attached directly to the nitrogen atom or via a benzene ring; and
/or containing at least one ester thereof and/or at least one non-toxic, pharmaceutically acceptable salt thereof, in admixture with a solid or liquid pharmaceutical diluent or carrier. - View Dependent Claims (13)
- ##STR7## wherein X is an --SO2 -- or --CO-- group and R is either phenyl or carboxymethylphenyl radical or is a radical of the general formula --(CH2)n --Y, in which Y is a hydroxyl group, an amino group or a monoalkyl- or dialkyl-amino group, the alkyl moieties of which contain up to 6 carbon atoms or a carboxylic or sulphonic acid group and n is a whole number of from 1 to 6 and in which one or more hydrogen atoms in the alkylene radical can be replaced by amino groups, monoalkyl- or dialkyl-amino groups, the alkyl moieties of which contain up to 6 carbon atoms or alkyl radicals and in which the --(CH2)n --Y radical is either attached directly to the nitrogen atom or via a benzene ring; and
Specification
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- Resources
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Current AssigneeBiorex Laboratories Limited
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Original AssigneeBiorex Laboratories Limited
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InventorsChan, Rosalind P. K.
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Primary Examiner(s)Tanenholtz, Alvin E.
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Assistant Examiner(s)Pepper, Frederick W.
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Application NumberUS06/281,504Time in Patent Office846 DaysField of Search260/207, 424/226US Class Current514/150CPC Class CodesA61P 1/04 for ulcers, gastritis or re...C07C 245/08 with the two nitrogen atoms...C09B 29/14 Hydroxy carboxylic acids
