John Wyeth Brother, Limited

American Home Products Corporation

John Weyth & Brother Limited

Kenneth Heatherington

Roger Crossley

John Leheup Archibald

The invention concerns a compound formula II ##STR1## or an acid addition salt thereof, wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, and R.sup.7 are the same or different and represent hydrogen, or loweralkyl, cycloalkyl or lower aralkyl, any of which radicals may be substituted by lower alkyl, lower alkoxy or CF.sub.3 or phenyl radicals which may be substituted by lower alkyl or CF.sub.3 or R.sup.2 and R.sup.3 taken together, form a 5, 6 or 7 membered saturated ring R.sup.4 and R.sup.5 may also represent lower alkoxy, or cycloalkoxy, n is 1, 2, or 3 and, if more than one R.sup.4 radical is present the R.sup.4 radicals may be the same or different with the provisos that (1) when R.sup.1, R.sup.2, R.sup.3, R.sup.4, and R.sup.5 are all hydrogen, R.sup.6 R.sup.7 are not both hydrogen, (2) when R.sup.1 and R.sup.3 are both phenyl and when R.sup.1 is methyl and R.sup.4 is methyl then R.sup.6 and R.sup.7 are not both methyl, and (3) when R.sup.1 is hydrogen or methyl, R.sup.3 is hydrogen or methyl and R.sup.2, R.sup.4, R.sup.5, and R.sup.6 are all hydrogen then R.sup.7 is other than unsubstituted phenyl. The compounds are intermediates for other compounds with anti-ulcer activity.

Quinoline derivatives

The invention provides a compound of formula III ##STR1## or an acid addition salt thereof, wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 are the same or different and represent hydrogen or lower alkyl, cycloalkyl, lower aralkyl or phenyl radicals any of which radicals may be substituted by lower alkyl, lower alkoxy or trifluoromethyl or R.sup.2 and R.sup.3 taken together, form a 5, 6 or 7 membered saturated ring, R.sup.4 and R.sup.5 may also represent lower alkoxy or cycloalkoxy, n is 1, 2 or 3 and, if more than one R.sup.4 radical is present the R.sup.4 radicals may be the same or different and esters of carboxylic acids with the hydroxy group shown, wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and n are as defined above, with the provisos that (1) R.sup.6 and R.sup.7 are other than hydrogen when R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are all hydrogen and (2) R.sup.6 and R.sup.7 are not both methyl when R.sup.4 is methyl. Compounds III are intermediates for other compounds with anti-ulcer or anti-secretory activity. Some of the compounds III are intermediates for anti-inflammatory agents.

A process for preparing dihydro compounds of formula I, by rearranging compounds of formula II, e.g. in the presence of acids or noble metal catalysts, is described. The compounds II may be prepared from intermediates of formula III. ##STR1## In these formulae R.sup.1,R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 are the same or different and represent hydrogen, or alkyl, cycloalkyl, aralkyl, or aryl radicals any of which radicals may be substituted, or R.sup.1 and R.sup.2 taken together or R.sup.2 and R.sup.3 taken together, form a 5, 6 or 7 membered ring which may be saturated or unsaturated and substituted or unsubstituted, R.sup.4 and R.sup.5 may also represent alkoxy, or cycloalkoxy, n is 1, 2 or 3 and, if more than one R.sup.4 radical is present the R.sup.4 radicals may be the same or different and R.sup.6 and R.sup.7 represent hydrogen, alkyl, cycloalkyl, or aralkyl radicals. Most of the compounds I, II and III are novel and are claimed. They are intermediates for anti-ulcer agents.

Certain novel 4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c] pyridine derivatives and their pharmacologically acceptable salts are described. These compounds provide potent and non-toxic compositions for the treatment of hypertension. Certain of the disclosed compounds also display activity as anti-tremor agents.

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Burnham, United Kingdom

Kenneth Heatherington