1,2,3,4,4a,10b-Hexahydro- and 1,2,3,4,4a,5,6,10b-octahydrophenanthridines, substituted in the 9-postion with hydroxy, lower alkoxy, hydroxy-substituted lower alkoxy or lower alkoxy-substituted lower alkoxy and whose 10b-carbon atom is quaternized with lower alkyl, lower cycloalkyl-alkyl or lower alkenyl, are described. The end products are useful as analgesic agents.
This is a division, of application Ser. No. 869,936 filed Oct. 27, 1969 and now abandoned, which in turn is a continuation-in-part of application Ser. No. 559,739, filed June 23, 1966, now U.S. Pat. No. 3,499,901, issued Mar. 10, 1970.
Pharmaceutical compositions comprising the combination of a benzodiazepine and certain 1,9-dihydroxyoctahydrophenanthridine and 1-hydroxyhexahydrophenanthridine-9(8H)-one analgesic agents to enhance the binding of said benzodiazepine to central benzodiazepine receptors, and a method for the use thereof.
There is disclosed substituted alkenones of Formula I ##STR1## wherein R.sup.1 is alkyl or acylamino each having 1 to 4 carbon atoms, hydrogen, or halogen, R.sup.2 and R.sup.3 individually are hydrogen, methyl or ethyl, R.sup.4 is hydrogen or dimethoxyphenyl, and n is 1 or 2, or physiologically acceptable acid addition salts thereof. Intermediates are also disclosed, along with methods of preparation of both the intermediates and the end products. The end products are useful as .beta. adrenolytic and anti-hypertensive agents. They are useful in the treatment of angina pectoris, hypertension, and arrhythmia.
Compounds having the formula ##STR1## R.sub.1 is hydrogen, benzyl or an ester moiety; Y is --CH(R.sub.2 ")CH(R.sub.2)-- or --CH(R.sub.3)CH hd 2--; R.sub.2 " is hydrogen or methyl; R.sub.2 is OH or X-substituted (C.sub.1-6)alkyl; R.sub.3 is OH, cyano or X-substituted (C.sub.1-3)alkyl; X is --OR.sub.6, --SR.sub.6, --S(O)R.sub.6, --S(O).sub.2 R.sub.6, --NR.sub.6 R.sub.7, --COOR.sub.7, --CONR.sub.7 R.sub.8 or oxo; with the proviso that when X is --NR.sub.6 R.sub.7, --COOR.sub.7 or --CONR.sub.7 R.sub.8, said group is located on the terminal carbon atom of R.sub.2 or R.sub.3 ; R.sub.6 is hydrogen, (C.sub.1-6)alkyl or acetyl; each of R.sub.7 and R.sub.8 is hydrogen or (C.sub.1-6)alkyl; s is an integer of 1 or 2; with the proviso that when R.sub.6 is acetyl, R.sub.7 is hydrogen and X is other than S(O)R.sub.6 or S(O).sub.2 R.sub.6 ; Z-W is alkyl, phenylalkyl or pyridylalkyl which can have an oxygen atom as part of the alkyl chain, and their use as CNS agents, antidiarrheals and anti-emetics. Processes for their preparation and intermediates therefor are described.
Compounds having the formula ##STR1## R.sub.1 is hydrogen, benzyl or an ester moiety; Y is --CH(R.sub.2 ")CH(R.sub.2)-- or --CH(R.sub.3)CH.sub.2 --; R.sub.2 " is hydrogen or methyl; R.sub.2 is OH or X-substituted (C.sub.1-16) alkyl; R.sub.3 is OH, cyano or X-substituted (C.sub.1-3) alkyl; X is --OR.sub.6, --SR.sub.6, --S(O)R.sub.6, --S(O).sub.2 R.sub.6, --NR.sub.6 R.sub.7, --COOR.sub.7, --CONR.sub.7 R.sub.8 or oxo; with the proviso that when X is --NR.sub.6 R.sub.7, --COOR.sub.7 or --CONR.sub.7 R.sub.8, said group is located on the terminal carbon atom of R.sub.2 or R.sub.3 ; R.sub.6 is hydrogen, (C.sub.1-6) alkyl or acetyl; each of R.sub.7 and R.sub.8 is hydrogen or (C.sub.1-6) alkyl; s is an integer of 1 or 2; with the proviso that when R.sub.6 is acetyl, R.sub.7 is hydrogen and X is other than S(O)R.sub.6 or S(O).sub.2 R.sub.6 ; z-w is alkyl, phenylalkyl or pyridylalkyl which can have an oxygen atom as part of the alkyl chain, and their use as CNS agents, antidiarrheals and antiemetics. Processes for their preparation and intermediates therefor are described.
Cycloalkanones, cycloalkanols and unsaturated analogs thereof, each of which has at the 3-position a 2-hydroxy-4-substituted phenyl group wherein the 4-position substituent is alkyl which can have an oxygen atom as part of the chain, or aralkyl which can have an oxygen atom as part of the alkyl chain, their use for pharmacological and medicinal purposes, intermediates therefor and processes for their preparation.
