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Antihypertensive 4-aminoquinolines
| Details |
Inventors: McCall, John M.;
Assignee: The Upjohn Company (Kalamazoo, MI)
Primary Examiner: Coughlan, Jr.; Paul M.
Assistant Examiner:
Attorney, Agent or Firm: Armitage; Robert A., Berneis; Hans L.
Antihypertensive compounds of the formula ll ##STR1## wherein X is chloro or trifluoromethyl; wherein R is an aromatic heterocyclic radical selected from the group consisting of triazinyl, pyrazinyl, pyridinyl, pyrimidinyl or the above radicals substituted by one or two trifluoromethyl, alkyl, alkoxy, dialkylamino, alkylthio, or halo, or 1 to 4 halo atoms for pyridine, or combinations of substituents, in which alkyl and alkoxy are each of 1 to 3 carbon atoms, inclusive, and halo is fluoro, bromo or chloro, or R is the group ##STR2## in which R.sub.1 is phenyl, phenyl-substituted with one or two halogens, trifluoromethylphenyl, phenyl-substituted with one or two alkoxy or alkyl groups, or alkylphenylsulfonyl, in which alkyl, alkoxy, and halo are defined as above; or R is the group SO.sub.2 R.sub.2, in which R.sub.1 is dialkylamino, phenyl, phenyl-substituted with one or two halogens, alkyl, trifluoromethyl or alkoxy groups, in which alkyl, alkoxy and halo are defined as hereinabove, are prepared from compounds of the formula ##STR3## WHEREIN X has the significance as above, by reaction with the selected cyclic amine or by reaction of ##STR4## wherein X is defined as above and a selected R.sub.2 -sulfonyl chloride or R.sub.1 -isocyanate. The compounds of formula ll and their pharmacologically acceptable acid addition salts are hypotensive agents which are useful for the treatment of hypertension in mammals, including man. |
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DETAILED DESCRIPTION I claim: 1.
A compound of the formula II ##STR15## wherein X is chloro or trifluoromethyl; wherein R is (a) triazinyl; (b) pyrazinyl; (c) pyrimidinyl; (d) triazinyl, pyrazinyl, or pyrimidinyl substituted by one or two trifluoromethyl, alkyl, alkoxy, dialkylamino, alkylthio, or halo, wherein halo is fluoro, bromo, or iodo, wherein alkyl is of one to 3 carbon atoms, and wherein alkoxy is of one to 3 carbon atoms; (e) halopyridinyl of 1 to 4 halo atoms; (f) ##STR16## wherein R.
sub.
1 is phenyl, phenyl subsituted with one or two halo or trifluoromethylphenyl, phenyl substituted with one or two alkoxy, alkylphenyl, or alkylphenylsulfonyl, wherein alkyl, alkoxy and halo are as defined above; or (g) --SO.
sub.
2 R.
sub.
2, wherein R.
sub.
2 is dialkylamino, phenyl substituted with one or two halo, alkylphenyl, phenyl, or trifluoromethylphenyl, or phenyl substituted with one or two alkoxy groups; wherein alkyl, alkoxy, and halo are as defined above; or the pharmacologically acceptable acid addition salts thereof.
2.
A compound according to claim 1 of the formula IIA ##STR17## wherein X is chloro or trifluoromethyl; wherein R.
sub.
5 is (a) pyrimidinyl or pyrazinyl or the alkylthio-, alkyl-, halo- or alkoxy-substituted derivatives thereof, wherein halo is chloro or fluoro and alkyl and alkoxy are of 1 to 3 carbon atoms, (b) halopyridinyl; (c) --SO.
sub.
2 R.
sub.
6, wherein R.
sub.
6 is phenyl, alkylphenyl, halophenyl, alkoxyphenyl, in which alkoxy, alkyl and halo are defined as above; or (d) ##STR18## wherein R.
sub.
7 is phenyl, alkylphenyl, halophenyl, trifluoromethylphenyl, or alkylphenylsulfonyl, wherein halo and alkyl are defined as above; or the pharmacologically acceptable acid addition salts thereof.
3.
A compound according to claim 1 of the formula IIB ##STR19## wherein R.
sub.
8 is (a) pyrimidinyl and pyrazinyl or these groups substituted with methyl, methylthio, methoxy or chloro; (b) halopyridinyl; (c) --SO.
sub.
2 R.
sub.
9, wherein R.
sub.
9 is ##STR20## p-tolyl, p-chlorophenyl or p-fluorophenyl; or (d) ##STR21## wherein R
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