John Wyeth Brother, Limited

David George Hill

Roger Crossley

Adrian Charles Curran

Novel compounds of formula I ##STR1## are described wherein R is lower alkyl, phenyl or aralkyl of 7 to 12 carbon atoms, R.sup.1 is hydrogen, lower alkyl, hydroxyloweralkyl, loweralkoxyloweralkyl, lower alkoxy, halogen, formyl, phenyl, phenylalkyl or acetal [CH(OR.sup.2).sub.2 where R.sup.2 is lower alkyl, or two R.sup.4 radicals are joined to form a lower alkylene chain], m is 1 or 2, Z is an anion, A is an alkylene radical having from 1 to 3 carbon atoms, which may be substituted by lower alkyl of 1 to 6 carbon atoms, S is sulphur and X is a benzothiazole, benzimidazole, benzoxazole, or phenyl radical which may be substituted and acid addition or quaternary ammonium salts of compounds wherein X is a benzimidazole radical. The compounds are used for the treatment of ulcers or hypersecretion. Treatment methods are claimed as well as pharmaceutical compositions.

Dithiocompounds

The invention relates to new tetrahydroquinoline derivatives which are intermediates useful in the preparation of anti-ulcer agents. The new derivatives have formula (I) ##STR1## wherein M is sodium, potassium or lithium, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are the same or different and represent hydrogen, or a lower alkyl, or a phenyl radical, and any of R.sup.4, R.sup.5 and R.sup.6 may be a gem-di-lower alkyl radical.

Tetrahydroquinoline derivatives

The invention provides a compound of formula I, ##STR1## wherein R is hydrogen, alkyl of 1-6 carbon atoms, or COR.sup.3 where R.sup.3 is hydrogen, alkyl of 1-5 carbon atoms, alkenyl of 2 to 5 carbon atoms, alkynyl of 2 to 5 carbon atoms, or cycloalkyl of 3 to 5 carbon atoms, R.sup.1 is hydrogen or alkyl of 1-6 carbon atoms, R.sup.2 is alkyl of 1-6 carbon atoms and R.sup.3 is as above defined. The compounds are intended for use in the treatment of ulcers or hypersecretion in mammals.

4-Amido-2-alkoxy thiazoles and composition

The invention relates to novel cyclopentena[b,e]pyridine derivatives which have a thioamide group in the 7-position. The compounds are anti-ulcer agents.

1,2,3,5,6,7-Hexahydrodicyclopenta[b,e]pyridine derivatives

The invention relates to novel pyridine derivatives which have a fused 5,6, or 7-membered saturated hydrocarbon ring adjacent to the nitrogen of the pyridine ring, and a group X situated on said hydrocarbon ring and separated by one carbon atom from the pyridine nitrogen atom, said group X is cyano, CONHR.sup.3, CSNHR.sup.3 or CO.sub.2 R.sup.5 wherein R.sup.3 is selected from hydrogen, lower alkyl and lower aralkyl radicals and R.sup.5 is selected from hydrogen, lower alkyl and lower aralkyl radicals which may be substituted by alkyl, alkoxy, halogen, nitro or trifluoromethyl; other substituents may be present. Compounds wherein X is CSNHR.sup.3 are anti-ulcer agents and the other compounds are intermediates therefor.

Certain 5,6,7,8-tetrahydroquinoline-8-thiocarboxamides

The invention provides 5,6,7,8-tetrahydroquinoline derivatives which are substituted at the 8-position by the group NHCSNHR.sup.5 where R.sup.5 is lower alkanoyl or aroyl. These compounds are intermediates for corresponding compounds where R.sup.5 is hydrogen, such compounds being anti-ulcer agents.

The invention relates to pharmaceutical compositions containing 5,6,7,8-tetrahydroquinoline-8-thioamides and nitriles and related tricyclic compounds and methods of treating ulcers using said compounds.

Pharmaceutical compositions containing 5,6,7,8-tetrahydroquinoline

The invention relates to novel cyclopenteno[b]pyridine derivatives which have a thioamide group in the 7-position and related tricyclic compounds. The compounds are anti-ulcer agents.

Cyclopenteno[b]pyridine derivatives

The invention relates to novel cyclopenteno[b]pyridine derivatives which have a group X on the 7-position and related tricyclic compounds. X is CONHR.sup.3, or CO.sub.2 R.sup.5 wherein R.sup.3 is hydrogen or lower alkyl and R.sup.5 is hydrogen or a lower alkyl or lower aralkyl group which may be substituted by alkyl, alkoxy, halogen, nitro or trifluoromethyl; other substituents may be present. The compounds are intermediates for compounds wherein X is CSNHR.sup.3 which are anti-ulcer agents.

The invention provides 5,6,7,8-tetrahydroquinoline derivatives which are substituted at the 8-position by an amino group. The 8-amino compounds are intermediates for corresponding thiocarbamoyl derivatives which are anti-ulcer agents.

8-Amino-5,6,7,8-tetrahydroquinoline derivatives

The invention relates to novel 8-cyano-5,6,7,8-tetrahydroquinoline derivatives which are intermediates for the preparation of corresponding 8-thioamides. Some of the 8-cyano compounds are anti-ulcer agents.

8-Cyano-5,6,7,8-tetrahydroquinoline derivatives

The invention relates to novel 5,6,7,8-tetrahydroquinoline derivatives which have a group X situated at the 8-position said group X is CONHR.sup.3, or CO.sub.2 R.sup.5 wherein R.sup.3 is hydrogen lower alkyl and R.sup.5 is hydrogen, lower alkyl or a lower aralkyl radical. The compounds are intermediates for corresponding compounds where X is CSNHR.sup.3 and these are anti-ulcer agents.

8-Carboxylester, and 8-carbamyl derivitives of

The invention provides 5,6,7,8-tetrahydroquinoline derivatives which are substituted at the 8-position by an amino group or the group NHCSNHR.sup.5 where R.sup.5 is hydrogen, alkyl of 1 - 3 carbon atoms which may be substituted by dialkylamino; lower alkanoyl or aroyl. The 8-amino cmpounds and those where R.sup.5 is lower alkanoyl or aroyl are intermediates. The other compounds are anti-ulcer agents.

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Cookham, United Kingdom

David George Hill