N-Substituted 2-(8-halo and trifluoromethyl 4-quinolylamino)benzamides and analgesic use thereof
AssigneeJohn Wyeth & Brother Limited
InventorsJohn L. Archibald, John T. A. Boyle
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Abstract
The disclosure describes new 4-aminoquinoline derivatives of general formula ##STR1## and their pharmaceutically acceptable acid addition salts, where X is trifluoromethyl or halogen, Z is hydrogen or a defined substituent and R is a group having one of the formulae ##STR2## where R.sup.1 is hydrogen or lower alkyl, R.sup.2 is lower alkyl, R.sup.3 is lower alkyl and A is lower alkylene. The new 4-aminoquinoline derivatives show analgesic activity and, in some cases, anti-inflammatory activity.
Claims13
A compound having the formula ##STR11## or a pharmaceutically acceptable acid addition salt thereof, wherein X is selected from trifluoromethyl and halogen, Z is selected from hydrogen, halogen, lower alkyl, lower alkoxy, nitro, di(lower alkyl) amino and trifluoromethyl and R is selected from the groups having the formulae ##STR12## wherein R.sup.1 is selected from hydrogen and lower alkyl, R.sup.2 is lower alkyl, R.sup.3 is lower alkyl and A is lower alkylene.
A pharmaceutical composition useful as an analgesic comprising a pharmaceutically acceptable carrier and an active amount of a compound having the formula:
- ##STR13## or a pharmaceutically acceptable acid addition salt thereof, wherein X is selected from trifluoromethyl and halogen, Z is selected from hydrogen, halogen, lower alkyl, lower alkoxy, nitro, di(lower alkyl) amino and trifluoromethyl and R is selected from the groups having the formulae ##STR14## where R.sup.1 is selected from hydrogen and lower alkyl, R.sup.2 is lower alkyl, R.sup.3 is lower alkyl and A is lower alkylene.
A method of providing analgesia in a mammal in need thereof, which comprises administering to said mammal an analgesic effective dose of a pharmaceutical composition comprising a pharmaceutical acceptable carrier and an active amount of a compound having the formula:
- ##STR15## or a pharmaceutically acceptable acid addition salt thereof, wherein X is selected from trifluoromethyl and halogen, Z is selected from hydrogen, halogen, lower alkyl, lower alkoxy, nitro, di(lower alkyl) amino and trifluoromethyl and R is selected from the groups having the formulae ##STR16## where R.sup.1 is selected from hydrogen and lower alkyl, R.sup.2 is lower alkyl, R.sup.3 is lower alkyl and A is lower alkylene.
A method of providing analgesia in a mammal in need thereof, which comprises administering to said mammal an analgesic effective dose of a pharmaceutical composition comprising a pharmaceutically acceptable carrier and an active amount of a compound selected from the group consisting of N-(1-ethyl-3-piperidyl-2-(8-trifluoromethyl-4-quinolylamino)benzamide, N-(2-diethylaminoethyl)-N-ethyl-2-(8-trifluoromethyl-4-quinolylamino)benza mide, N-(1-ethyl-4-piperidyl)-2-(8-trifluoromethyl-4-quinolylamino)benzamide and 2-(8-chloro-4-quinolylamino)-N-(2-diethylaminoethyl)-N-ethylbenzamide or a pharmaceutical acceptable acid addition salt thereof.
Dependencies are inferred from the claim text.