Hoffmann-la Roche Inc.

Ciba-geigy Corporation

Rudolf Pfister

Dieter Binder

Otto Hromatka

Paul Zeller

Emilio Kyburz

Alfred Sallmann

Albert E Fischli

Quirico Branca

Hans Bruderer

Werner Aschwanden

Peter M Muller

Rene Urban

1-[2-(4,5,10,11-Tetrahydro-1H-dibenzo[a,d]cyclohepten-5-yl)ethyl]pyrrolidin e of the formula ##STR1## and its pharmaceutically acceptable acid addition salts, prepared through various intermediates, are described. The compounds have valuable histamine-H.sub.1 antagonistic properties and are suitable for the control or prevention of allergic reactions,such as, urticaria, hay fever, anaphylaxis and over-sensitivity to medicaments.

Derivatives of 10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-ethanol

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

1-[2-(4,5,10,11-Tetrahydro-1H-dibenzo[a,d]cyclohepten-5-yl)ethyl]pyrrolidin e of the formula ##STR1## and its pharmaceutically acceptable acid addition salts, prepared through various intermediates, are described. The compounds have valuable histamine-H.sub.1 antagonistic properties and are suitable for the control or prevention of allergic reactions, such as, urticaria, hay fever, anaphylaxis and over-sensitivity to medicaments.

Cycloheptene derivatives

Cyclohexenes of the formula ##STR1## wherein R.sup.1 is hydroxy or lower alkoxy; n is 1 or 2; R.sup.2 is lower alkyl; and R.sup.3 is hydrogen, lower alkyl, lower alkenyl or lower cycloalkylmethyl, and their pharmaceutically acceptable acid addition salts are disclosed. The compounds of formula I have analgesic activity and are useful for the control of pains.

Cyclohexene derivatives

The invention relates to thiazine derivatives of the formula ##STR1## wherein R.sup.1 is lower alkyl and R.sup.2 is the residue of an aromatic heterocycle containing 1 to 4 hetero atoms optionally substituted by one or two lower alkyl groups, or a phenyl or benzyl group optionally substituted by halogen, hydroxy, lower alkyl, trifluoromethyl, nitro or lower alkoxy, and pharmaceutically acceptable salts thereof. The compounds of formula I are useful for the control or prevention of inflammation, pains, rheumatics and thromboses.

Thiazine derivatives

Cyclohexene derivative analgesics

Cyclohexadiene derivatives of the formula ##STR1## wherein R.sup.1,R.sup.2,R.sup.3 and R.sup.4 are as hereinafter set forth, are described. The compounds of formula I are useful as analgesic agents.

Phenyl-cyclohexadiene-alkylamine 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.

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.

Phenylacetohydroxamic acids having the formula I ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4, independently of each other, represent hydrogen, chlorine, fluorine or bromine atoms or an alkyl or alkoxy group having at most 6 carbon atoms, and wherein R.sub.2 may additionally represent a trifluoromethyl group with the proviso that R.sub.1, R.sub.2 and R.sub.3 may not simultaneously represent hydrogen atoms and their pharmaceutically acceptable salts with bases, which compounds inhibit plateletaggregation and exhibit valuable pharmacological, in particular, antiphlogistic, analgesic and antipyretic activity.

Phenylacetohydroxamic acids

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.

Growing community of inventors

Basel, Switzerland

Rudolf Pfister