Patent GB-1172426-A (GB)
Title: Imidazo-(1,5-a)-quinoline Derivatives
Inventor: WRIGHTS WILLIAM JR
IPC: C07D471/04
Filed: 1967-02-08
Abstract: 1,172,426. Imidazo - (1,5-a) - quinoline derivatives. AMERICAN CYANAMID CO. 8 Feb., 1967 [18 Feb., 1966], No. 6130/67. Heading C2C. Novel compounds of Formula I or a pharmaceutically acceptable acid addition salt thereof; wherein R and R 1  are hydrogen, halogen, lower alkyl, lower alkoxy or trifluoromethyl; R 2  is hydrogen, lower alkyl or halogen, Y is oxygen or sulphur; n is an integer from 1 to 4; and R 3  and R 4  are hydrogen, lower alkyl, lower alkenyl, cycloalkyl, aralkyl, or lower (cycloalkyl) methyl, or -NR 3 R 4 , when taken together, is 1-pyrrolidinyl, lower alkyl-1-pyrrolidinyl, piperidino, lower alkylpiperidino, morpholino, lower alkylmorpholino, hexamethyleneimino, 1-piperazinyl, 1 -(lower alkyl) -4-piperazinyl, 1 -(hydroxy lower alkyl)-4-piperazinyl, 1 - (lower alkanoyloxyalkyl) - 4 - piperazinyl- 1 - phenyl - 4 - piperazinyl, 1 - (lower alkoxyphenyl) - 4 - piperazinyl, 1 - trifluoromethyl, phenyl - 4 - piperazinyl, 1 - (lower alkylphenyl)- 4 - piperazinyl, 1 - halophenyl - 4 - piperazinyl, 4 - phenyl - 1,2,4,5 - tetrahydro - 1 - pyridinyl, 4 - alkylphenyl - 1,2,5,6 - tetrahydro - 1- pyridinyl, 4 - halophenyl - 1,2,5,6 - tetrahydro- 1 - pyridinyl, 4 - lower alkoxyphenyl - 1,2,5,6- tetrahydro - 1 - pyridinyl, 4 - trifluoromethylphenyl - 1,2,5,6 - tetrahydro - 1 - pyridinyl or azabicyclo - [3.2.2] - nonan - 3 - yl; or -C n H 2n - NR 3 R 4 , when taken together, is (2-pyrrolidinyl)- lower alkyl, (3-pyrrolidinyl) lower alkyl, (1- lower alkylpyrrolidinyl) lower alkyl, (1-benzylpyrrolidinyl) - lower alkyl, [1 - (halobenzyl)- pyrrolidinyl - lower alkyl, (1 - lower alkylpyrrolidinyl) - lower alkyl, (1 - benzylpyrrolidinyl) - lower alkyl, [1 - (halobenzyl) - pyrrolidinyl] - lower alkyl, [1 - (lower alkoxybenzyl)- pyrrolidinyl] - lower alkyl, [1 - (lower alkylbenzyl) - pyrrolidinyl] - lower alkyl, piperidinyl lower alkyl, (1-lower alkyl piperdinyl)- lower alkyl, (1 -benzylpiperidinyl)-lower alkyl, [1 - (halobenzyl) - piperidinyl] - lower alkyl, [1 - (lower alkoxybenzyl) - piperidinyl] - lower alkyl, or [1 - (lower alkylbenzyl) - piperidinyl]- lower alkyl and radicals qualified by the term " lower " contain up to 4 carbon atoms are prepared either (a) by heating a compound of Formula II wherein Z is H or -C n H 2n X wher X is halogen, (C 1 -C 4 ) alkylsulphonyloxy or arylsulphonyloxy, (1) when Z is H, with a compound of formula X-C n H 2n NR 3 R 4  or (2) when Z is C n H 2n X 1  with a compound of formula H-NR 3 - R 4 , in both eases optionally followed by reacting the product with P 2 S 5  and/or salt formation and/or removal of a group R 3  is benzyl by hydrogenolysis or (b) reacting a compound of formula with a cyclizing agent providing a carbonyl or thioketone group such as phosgene, thiophosgene, ethyl chloroformate or N,N<SP>1</SP>-carbonyl diimidazole or (c) where n is 1 by reaction of a compound of Formula II above with formaldehyde/formic acid and a compound of formula HNR 3 R 4 . 2 - (3 - Bromopropyl) - 3,3a,4,5 - tetrahydroimidazo - [1,5-a] - quinolin - 1 - (2H) - one is prepared by reaction of 1,3-dibromopropane and the 2-unsubstituted compound. Pharmaceutical compositions in conventional forms for oral administration and having tranquilizing activity comprise an above novel compound or salt and a carrier therefor.