4-Aryloxy-1,2,3,4-tetrahydroisoquinolines
AssigneeHoechst-Roussel Pharmaceuticals Inc.
InventorsRichard C. Effland, Larry Davis, Joseph T. Klein
Life of this patent
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Abstract
This invention relates to 4-aryloxy-1,2,3,4-tetrahydroisoquinolines of the formula ##STR1## , where Y is hydrogen and alkoxy; X is hydrogen, cyano, benzoyl, trifluoromethyl, phenyl, halogen, alkyl alkoxy and nitro; R is hydrogen and alkyl; R.sub.1 is hydrogen, alkyl, aralkyl, ##STR2## and CO.sub.2 R.sub.4 where R.sub.4 is aryl and alkyl; R.sub.2 and R.sub.3 are the same or different and are hydrogen and alkyl or R.sub.2 and R.sub.3 are fused together to form a pyrrolidino or a piperidino ring substituent; and m is an integer of 1 or 2; n is an integer of 2 or 3; and a pharmaceutically acceptable acid addition salt thereof.
Claims32
A 4-aryloxy-1,2,3,4-tetrahydroisoquinoline having the formula ##STR20## where Y is hydrogen and alkoxy of 1 to 6 carbon atoms;
- X is hydrogen, cyano, benzoyl, trifluoromethyl, phenyl, halogen, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms and nitro;
- R is hydrogen and alkyl of 1 to 6 carbon atoms;
- R.sub.1 is hydrogen, alkyl and ##STR21## where R.sub.2 and R.sub.3 are the same or different and are hydrogen and alkyl of 1 to 6 carbon atoms or R.sub.2 and R.sub.3 are fused together to form a pyrrolidino or a piperidino ring substituent;
- m is an integer of 1 or 2;
- n is an integer of 2 or 3;
- and a pharmaceutically acceptable acid addition salt thereof.
An anticonvulsant composition which comprises an anticonvulsant effective amount of a compound having the formula ##STR22## where Y is hydrogen and alkoxy of 1 to 6 carbon atoms;
- X is hydrogen, cyano, benzoyl, trifluoromethyl, phenyl, halogen, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms and nitro;
- R is hydrogen and alkyl of 1 to 6 carbon atoms;
- R.sub.1 is hydrogen, alkyl and ##STR23## where R.sub.2 and R.sub.3 are the same or different and are hydrogen and alkyl or R.sub.2 and R.sub.3 are fused together to form a pyrrolidino or a piperidino ring substituent, m is an integer of 1 or 2;
- n is an integer of 2 or 3;
- and a pharmaceutically acceptable acid addition salt thereof.
An analgesic composition which comprises an effective analgesic amount of a compound having the formula ##STR24## where Y is hydrogen and alkoxy of 1 to 6 carbon atoms;
- X is hydrogen, cyano, benzoyl, trifluoromethyl, phenyl, halogen, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms and nitro;
- R is hydrogen and alkyl of 1 to 6 carbon atoms;
- R.sub.1 is hydrogen, alkyl of 1 to 6 carbon atoms and ##STR25## where R.sub.2 and R.sub.3 are the same or different and are hydrogen and alkyl of 1 to 6 carbon atoms or R.sub.2 and R.sub.3 are fused together to form a pyrrolidino or a piperidino ring substittuent;
- m is an integer of 1 or 2;
- n is an integer of 2 or 3;
- and a pharmaceutically acceptable acid addition salt thereof.
A diuretic composition which comprises a diuretically effective amount of a compound selected from the group consisting of 4-(p-cyanophenoxy)-B 2-methyl-1,2,3,4-tetrahydroisoquinoline,
- 2-(2-N,N-dimethylaminoethyl)1,2,3,4-tetrahydro-4-(p-trifluoromethylphenoxy) isoquinoline, 2-(2-N,N-diethylaminoethyl)-1,2,3,4-tetrahydro-4-(p-trifluoromethylphenoxy )isoquinoline,
- 2-(3-piperidinopropyl)-1,2,3,4-tetrahydro-4-(p-trifluoromethylphenoxy)isoqu inoline and a pharmaceutically acceptable salt of any of the foregoing.
An antidepressant composition which comprises an antidepressant effective amount of a compound selected from the group consisting of 2-methyl-1,2,3,4-tetrahydro-4-(m-trifluoromethylphenoxy)isoquinoline,
- 2-methyl-4-(p-nitrophenoxy)-1,2,3,4-tetrahydroisoquinoline and a pharmaceutically acceptable acid addition salt of any of the foregoing.
Dependencies are inferred from the claim text.