4-[2-(Carbocycloalkoxymethyl)phenylimino]-1,4-dihydroquinolines bearing a chloro or trifluoromethyl group in the 7-position of the quinoline nucleus are anti-inflammatory and anti-malarial agents and can be prepared through treatment of a cycloalkyl 2-aminophenylacetate with the appropriate 4-chloroquinoline. A typical embodiment is 7-chloro-4-[2-(carbocyclohexyloxymethyl)phenylimino]-1,4-dihydroquinol ine.

Derivatives of 4-{8 2-(carbocycloalkoxymethyl) phenylimino{9 -1,4-dihydroquinolines

Novel 4-amino-quinolines of the formula WHEREIN R is selected from the group consisting of hydrogen, halogen, -CF3, lower alkyl, lower alkoxy, lower alkylsulfonyloxy, lower alkylthio, nitro, lower alkylamino, lower acylamino and cyano, R1 is selected from the group consisting of hydrogen, chlorine and methyl, Y is selected from the group consisting of 2,3 and 3,4-disubstituted thiophenes of the formula AND 4,5 DISUBSTITUTED THIAZOLES OF THE FORMULA WHEREIN R2 and Q are selected from the group consisting of hydrogen and lower alkyl and X is selected from the group consisting of hydrogen, lower alkyl, a phenyl, diloweralkylamino lower alkylene, N-morpholino lower alkylene, Z , R3 and R4 being hydrogen and taken together form P and P1 are lower alkyl, P2 is selected from the group consisting of lower alkyl and monocyclic aryl, M and M' are lower alkyl, Z is halogen and n is an integer from 1 to 6, and their non-toxic, pharmaceutically acceptable acid addition salts having analgesic and anti-inflammatory activity and their preparation. Lower alkyl means having 1 to 6 carbon atoms.

Novel quinolines in the treatment of pain and inflammation

4-[2-(Carbocycloalkoxymethyl)phenylimino]-1,4-dihydroquinolines bearing a chloro or trifluoromethyl group in the 7-position of the quinoline nucleus are anti-inflammatory and anti-malarial agents and can be prepared through treatment of a cycloalkyl 2-aminophenylacetate with the appropriate 4-chloroquinoline. A typical embodiment is 7-chloro-4-[2-(carbocyclohexyloxymethyl)phenylimino]-1,4-dihydroquinoline.

Derivatives of 4-[2-(carbocycloalkoxymethyl) phenylimino]-1,4-dihydroquinolines

Novel compounds of formula are prepared by transesterification of compounds of formula wherein R is alkyl and one X is H and the other Cl, with glycerol acetonide in the presence of an alkaline substance. 4 - (21 - Methoxycarbonylphenylamino) - 8 - chloroquinoline is prepared by reaction of 4,8-dichloroquinoline with methylanthranilate. Pharmaceutical compositions in conventional form for oral, rectal or transcutaneous administration comprise an above novel compound and one or more carriers or excipients.

Pierre Girault

Papers

Acetonides of alpha-monoglycerides of 4 - (2'-carboxyphenylamino)-chloroquinolines