Hoffmann-la Roche Inc.

Otto Hromatka

Dieter Binder

Paul Zeller

Rudolf Pfister

Joseph Hellerbach

4-Hydroxy-2-methyl-3-(2-pyridylcarbamoyl)-6-trifluoromethyl-2H-thieno[2,3-e ]-1,2-thiazine 1,1-dioxide of the formula ##STR1## and its pharmaceutically acceptable salts which possess valuable pharmacodynamic properties are described. More particularly, the compound and its salts display antiinflammatory, analgesic and antirheumatic activities and they are readily accessible by reacting a corresponding alkyl ester with 2-aminopyridine and, if desired, subsequent salt formation.

Antiinflammatory, analgesic, and antirheumatic

The invention relates to sulphothiophene-carboxylic acids of the following formula ##STR1## wherein A together with the two carbon atoms to which it is attached forms the group ##STR2## and the broken line represents the double bond present in group (a), R.sub.3 and R.sub.4 each represent a hydrogen atom or a lower alkyl group; and the halides and lower alkyl esters thereof.

Thiophene derivatives

The present invention relates to compounds of the formula ##STR1## wherein A together with the two carbon atoms to which it is attached forms the group ##STR2## and the broken line represents the double bond in group (a); R.sub.1 represents a lower alkyl group; R.sub.2 represents the residue of an aromatic heterocyclic ring containing from 1 to 4 hetero atoms, which may be substituted by one or two lower alkyl groups, or a phenyl group which may be substituted by halogen, hydroxy, lower alkyl, trifluoromethyl or lower alkoxy and R.sub.3 and R.sub.4 each represent a hydrogen atom or a lower alkyl group. Also provided are methods for their preparation. The thienothiazine derivatives provided by this invention have anti-flammatory, analgesic and anti-rheumatic activity.

Thienothiazine derivatives

Thienothiazine derivatives of the formula ##STR1## wherein A, R.sub.1 and R.sub.2 are as hereinafter set forth, and their tautomers are described. The thienothiazine derivatives are useful as anti-inflammatory, analgesic, antirheumatic and antithrombotic agents.

Thiazine derivatives

Anti-inflammatory, analgesic, anti-rheumatic and anti-thrombotic thienothiazine derivatives having the formula ##STR1## wherein A together with the two carbon atoms forms the group ##STR2## and the dotted line indicates the double bond present in the first and last thieno structures above, R.sup.1 is lower alkyl, R.sup.2 is the radical of an aromatic heterocycle with 1 to 4 hetero atoms optionally substituted by one or two lower alkyl groups, or a phenyl radical optionally substituted by halogen, hydroxy, lower alkyl, trifluoromethyl or lower alkoxy, R.sup.3 is halogen and R.sup.3' is hydrogen or halogen, and pharmaceutically acceptable salts thereof are described.

Thienothiazine derivatives of the formula ##STR1## wherein R.sub.1 is lower alkyl; R.sub.2 is an unsubstituted aromatic heterocyclic radical which contains from 1 to 4 hetero atoms or one which is substituted by one or two lower alkyl groups, or is an unsubstituted phenyl radical or one substituted by halogen, hydroxy, lower alkyl, nitro, trifluoromethyl or lower alkoxy; and R.sub.3 and R.sub.4, independently, are hydrogen or lower alkyl, prepared inter alia, from novel intermediates, are described. The end products are useful as anti-inflammatory, analgesic and anti-rheumatic agents.

Novel thienotriazolodiazepine derivatives and processes for their preparation are described. These compounds are useful as anticonvulsants, muscle-relaxants and sedatives.

Thienotriazolodiazepine derivatives

The present invention relates to compounds of the formula ##STR1## wherein A together with the two carbon atoms to which it is attached forms the group ##STR2## AND THE BROKEN LINE REPRESENTS THE DOUBLE BOND IN GROUP (A); R.sub.1 represents a lower alkyl group; R.sub.2 represents the residue of an aromatic heterocyclic ring containing from 1 to 4 hetero atoms, which may be substituted by one or two lower alkyl groups, or a phenyl group which may be substituted by halogen, hydroxy, lower alkyl, trifluoromethyl or lower alkoxy and R.sub.3 and R.sub.4 each represent a hydrogen atom or a lower alkyl group.

N-Carbalkoxymethylsulfamoyl thiophene carboxylic acid alkyl esters

Thienothiazine derivatives of the formula ##STR1## wherein R.sub.1 is lower alkyl; R.sub.2 is an unsubstituted aromatic heterocyclic radical which contains from 1 to 4 hetero atoms or one which is substituted by one or two lower alkyl groups, or is an unsubstituted phenyl radical or one substituted by halogen, hydroxy, lower alkyl, nitro, trifluoromethyl or lower alkoxy; and R.sub.3 and R.sub.4, independently, are hydrogen or lower alkyl, Prepared inter alia, from novel intermediates, are described. The end products are useful as anti-inflammatory, analgesic and anti-rheumatic agents.

The present invention relates to compounds of the formula ##STR1## wherein A together with the two carbon atoms to which it is attached forms the group ##STR2## AND THE BROKEN LINE REPRESENTS THE DOUBLE BOND IN GROUP (A); R.sub.1 represents a lower alkyl group; R.sub.2 represents the residue of an aromatic heterocyclic ring containing from 1 to 4 hetero atoms, which may be substituted by one or two lower alkyl groups, or a phenyl group which may be substituted by halogen, hydroxy, lower alkyl, trifluoromethyl or lower alkoxy and R.sub.3 and R.sub.4 each represent a hydrogen atom or a lower alkyl group. Also provided are methods for their preparation. The thienothiazine derivatives provided by this invention have anti-flammatory, analgesic and antirheumatic activity.

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Vienna, Austria

Otto Hromatka