John Wyeth Brother, Limited

USA As Represented by Secretary of the Navy

Adrian Charles Curran

Roger Crossley

David George Hill

Robin G Shepherd

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 relates to N-acyl thioureas which are derivatives of 1,5-Naphthyridines. The compounds are intermediates for anti-ulcer agents.

Certain 1-(N-acyl)-carbothioamides of 1,5-naphthyridine derivatives

The invention relates to thioureas which are derivatives of 1,5-Naphthyridines. The compounds are anti-ulcer agents or intermediates therefor.

Certain 1-carbothioamides of 1,5-naphthyridine derivatives

A new process for preparing 5-oxo-tetrahydroquinolines comprises condensing a compound of formula II with a ##STR1## compound of formula III to obtain a compound of formula I wherein R, R.sup.1, R.sup.2 and R.sup.3 are selected from hydrogen and lower alkyl. Compounds of formula I are intermediates for pharmaceuticals.

Preparation of quinoline derivatives

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 relates to novel silicon derivatives of tetrahydroquinolines, which are intermediates in a process for preparing 5,6,7,8-tetrahydroquinoline-8-carboxamides and thiocarboxamides.

Silicon derivatives of tetrahydroquinolines

The invention relates to magnesium halide derivatives of tetrahydroquinolines and related compounds. These are intermediates useful in the preparation of anti-ulcer agents.

Pyridine grignard derivatives

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 provides a compound of formula I ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and represent hydrogen or alkyl of 1-6 carbon atoms, R.sup.3 represents hydrogen, alkyl of 1-6 carbon atoms, or phenyl, X is Na, K, Li, or CSNHR.sup.4 wherein R.sup.4 is hydrogen or alkyl of 1-6 carbon atoms and n is 3, 4 or 5 or a pharmaceutically acceptacle acid addition salt of a compound where X is CSNHR.sup.4. The compounds of formula I wherein X is CSNHR.sup.4 are anti-ulcer agents. Those in which X is Na, K or Li are intermediates.

Phenanthridine derivatives and related compounds

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 thioureas which are derivatives of organic nitrogen compounds containing a pyridine ring to which is fused a saturated nitrogen containing ring which carries on its nitrogen atom a thioamide or substituted thioamide group. The compounds are anti-ulcer agents or intermediates therefor.

Certain 1-carbothioamides of 1,8-naphthyridines, pyrrolo(2,3-b)pyridines

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.

Growing community of inventors

South Cave, United Kingdom

Adrian Charles Curran