Alkylphenyl benzopyranopyridines

Abstract

Alkylphenyl benzopyranopyridines represented by the formula ##STR1## where R 1 is hydrogen, loweralkyl, loweralkanoyl, cycloalkylloweralkyl, cycloalkylloweralkanoyl, loweralkenyl, loweralkynyl, haloloweralkenyl, phenylloweralkyl, phenylloweralkenyl or phenylloweralkynyl; R 2 is loweralkyl; R 3 is hydrogen; Y is a straight or branched chain alkylene group having from one to ten carbon atoms; and each R 4 and R 5 and R 6 are the same or different members of the group consisting of hydrogen, halo, trifluoromethyl or loweralkyl; and the pharmaceutically acceptable salts thereof.

I claim: 
     
       1. A compound of the formula ##STR4## where R 1  is hydrogen, loweralkyl, 3-methyl-2-butenyl, .Iadd.propargyl, .Iaddend.3-chloro-2-propenyl, cyclopropylmethyl, phenylloweralkyl, or 3(3,4,5-trimethoxyphenyl)-2-propenyl; R 2  is methyl; R 3  is hydrogen; .[.Y is a radical of the formula ##STR5## where n is a linear chain of 1-9 carbon atoms and R 7  is H or CH 3  ; .Iadd.y is a straight or branched chain alkylene group having 4 to 7 carbon atoms and having no branch larger than a methyl group; .Iaddend.and each R 4  and R 5  and R 6  are the same or different members of the group consisting of hydrogen, halo, trifluoromethyl or loweralkyl; and the pharmaceutically acceptable salts thereof.   
     
     
       2. A compound in accordance with claim 1 wherein R 1  is benzyl. 
     
     
       3. A compound in accordance with claim 1 wherein R 1  is hydrogen. 
     
     
       4. A compound in accordance with claim 1 wherein R 1  is propargyl .[.and each R 2  is methyl.].. 
     
     
       5. A compound in accordance with claim 1 of the formula ##STR6## where R 1  is hydrogen, loweralkyl, 3-methyl-2-butenyl, .Iadd.2-propynyl, .Iaddend.3-chloro-2-propenyl, cyclopropylmethyl, phenylloweralkyl, or 3(3,4,5-trimethoxyphenyl)-2-propenyl; R 2  is methyl, Y is a radical of the formula .[. ##STR7##.]. .[.where n is a linear chain of 1-9 carbon atoms and R 7  is H or CH 3 . ##STR8## .Iadd.where n is an integer from 1 to 3 inclusive, R 7  is hydrogen or methyl and R 8  is hydrogen or methyl except that R 8  cannot be methyl if R 7  is hydrogen. .Iaddend. .[.   
     
     
       6.  A compound in accordance with claim 5, 2-benzyl-5,5-dimethyl-3-(4-fluorophenyl-1-methylbutyl)-10-hydroxy-1,2,3,4-tetrahydro-5H[1]benzopyrano[4,3-c]pyridin-10-ol..]. .[.7. A compound in accordance with claim 5, 5,5-dimethyl-3-(4-fluorophenyl-1-methylbutyl)-10-hydroxy-1,2,3,4-tetrahydr 
     
     
       o-5H[1]benzopyrano[4,3-c]pyridin-10-ol hydrochloride..]. .[.8.  A compound in accordance with claim 5, 5,5-dimethyl-3-(4-fluorophenyl-1-methylbutyl)-10-hydroxy-2-[2-propynyl)]-1,2,3,4-tetrahydro-5H[1]benzopyrano[4,3-c]pyridin-10-ol..]..Iadd. 9. 2-Benzyl-5,5-dimethyl-8-[4-(p-fluorophenyl)-1-methylbutyl]-10-hydroxy-1,2,3,4-tetrahydro-5H[1]benzopyrano[4,3-c]pyridine. .Iaddend..Iadd. 10. 5,5-Dimethyl-8-[4-(p-fluorophenyl)-1-methylbutyl]-10-hydroxy-1,2,3,4-tetrahydro-5H[1]benzopyrano[4,3-c]pyridine hydrochloride. .Iaddend..Iadd. 11. 5,5-Dimethyl-8-[4-(p-fluorophenyl)-1-methylbutyl]-10-hydroxy-2-(2-propynyl)-1,2,3,4-tetrahydro-5H[1]benzopyrano[4,3-c]pyridine. .Iaddend..Iadd. 12. A compound of the formula ##STR9## wherein R 1  is hydrogen, C 1  -C 6  alkyl, C 2  -C 6  alkenyl, C 2  - C 6  alkynyl, halo(C 2  -C 6 )alkenyl, halo (C 2  -C 6 ) alkynyl or phenyl (C 1  -C 6 ) alkyl; Y is a straight or branched chain alkylene group having from 4 to 7 carbon atoms and having no branch larger than a methyl group; and each R 4  and R 5  and R 6  are the same or different members of the group consisting of hydrogen, halo, trifluoromethyl or loweralkyl. 
     
     
        .Iaddend..Iadd. 13.  A compound in accordance with claim 12 of the formula ##STR10## wherein Y is a radical of the formula ##STR11## where n is an integer from 1 to 3 inclusive, R 7  is hydrogen or methyl and R 8  is hydrogen or methyl except that R 8  cannot be methyl 
     
     
        when R 7  is hydrogen. .Iaddend..Iadd. 14.  A compound in accordance with claim 13, 2-Benzyl-8[4-(p-fluorophenyl)-1-methylbutyl]-10-hydroxy-5-oxo-1,2,3,4-tetrahydro-5H[1]benzopyrano[4,3-c]pyridine. .Iaddend..Iadd. 15. A compound in accordance with claim 13, 8-[4-(p-fluorophenyl)-1-methylbutyl]-10-hydroxy-5-oxo-1,2,3,4-tetrahydro-5H[1]benzopyrano[4,3-c]pyridine. .Iadd. 16. A pharmaceutical composition in unit dosage form comprising an analgesic effective amount of a compound of claim 1 and a pharmaceutically acceptable carrier or diluent. .Iaddend..Iadd. 17. A pharmaceutical composition in accordance with claim 16 wherein said compound is 5,5-Dimethyl-8-[4-(p-fluorophenyl)-1-methylbutyl] -10-hydroxy-2-(2-propynyl)-1,2,3,4-tetrahydro-5H[1]benzopyrano[4,3-c]pyridine. .Iaddend..Iadd. 18. A method of relieving pain comprising administering a therapeutically effective amount of a compound of claim 1 to a patient in need of such treatment. .Iaddend..Iadd. 19. The method of claim 18 wherein the compound is 5,5-dimethyl-8-[4-(p-fluorophenyl)-1-methylbutyl]-10-hydroxy-2-(2-propynyl)-1,2,3,4-tetrahydro-5H[1]benzopyrano[4,3-c]pyridine. .Iaddend.