Pfizer Corporation

Thomas H Althuis

Michael Ross Johnson

Lawrence S Melvin, Jr

Charles A Harbert

Hans-Jurgen E Hess

Saul B Kadin

Leonard J Czuba

Azacycloalkanes, and derivatives thereof, including unsaturated analogs, 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.

3-[2-Hydroxy-4-(substituted)phenyl]azacycloalkanols and derivatives

Compounds of the formula ##STR1## wherein R.sub.1 is hydrogen, benzyl, benzoyl, alkanoyl of 1 to 5 carbon atoms or --CO--(CH.sub.2).sub.p --NR'R' wherein p is 0 or an integer from 1 to 4; each of R' and R' when taken individually is hydrogen or alkyl of 1 to 4 carbon atoms; R' and R' when taken together with the nitrogen to which they are attached form a 5- or 6-membered heterocyclic ring selected from piperidino, pyrollo, pyrrolidino, morpholino and N-alkylpiperazino having from 1 to 4 carbon atoms in the alkyl group;

1,9-Dihydroxyoctahydrophenanthrenes

3-(2-Hydroxy-4-(substituted)phenyl)azacycloalkanes as analgesics

Compounds of the formula ##STR1## wherein R.sub.1 is hydrogen, benzyl, benzoyl, alkanoyl of 1 to 5 carbon atoms or --CO--(CH.sub.2).sub.p --NR'R' wherein p is 0 or an integer from 1 to 4; each of R' and R' when taken individually is hydrogen or alkyl of 1 to 4 carbon atoms; R' and R' when taken together with the nitrogen to which they are attached form a 5- or 6-membered heterocyclic ring selected from piperidino, pyrrolo, pyrrolidino, morpholino and N-alkylpiperazino having from 1 to 4 carbon atoms in the alkyl group;

Intermediates to 1,9-dihydroxyoctahydrophenanthrenes

Compounds useful for pharmacological and medicinal purposes having the formulae ##STR1## wherein R is H, C.sub.1 -C.sub.5 alkanoyl; R.sub.1 is H, benzyl, C.sub.1 14 C.sub.5 alkanoyl, P(O)(OH).sub.2, --CO(CH.sub.2).sub.2 COOH or a basic acyl group; each of R.sub.2 and R.sub.4 is H, C.sub.1 -C.sub.6 alkyl, phenyl, pyridyl or (CH.sub.2).sub.y C.sub.6 H.sub.5 ; y is 1-4; R.sub.3 is H or CH.sub.3 ; Z is C.sub.1 -C.sub.13 alkylene or --(alk.sub.1).sub.m --O--(alk.sub.2).sub.n --; each of (alk.sub.1) and (alk.sub.2) is C.sub.1 -C.sub.13 alkylene with the proviso that the summation of carbon atoms in (alk.sub.1) plus (alk.sub.2) is not greater than 13; each of m and n is 0 or 1; and W is H, pyridyl, phenyl, fluorophenyl or chlorophenyl; intermediates therefor and methods for their preparation and use.

Hydroxyalkyl and oxoalkyl substituted phenols as analgesics and sedatives

Compounds useful for pharmacological and medicinal purposes having the formulae ##STR1## wherein R is H, C.sub.1 -C.sub.5 alkanoyl; R.sub.1 is H, benzyl, C.sub.1 -C.sub.5 alkanoyl, P(O)(OH).sub.2, --CO(CH.sub.2).sub.2 COOH or a basic acyl group; each of R.sub.2 and R.sub.4 is H, C.sub.1 -C.sub.6 alkyl, phenyl, pyridyl or (CH.sub.2).sub.y C.sub.6 H.sub.5 ; y is 1-4; R.sub.3 is H or CH.sub.3 ; Z is C.sub.1 -C.sub.13 alkylene or --(alk.sub.1).sub.m --O--(alk.sub.2).sub.n --; each of (alk.sub.1) and (alk.sub.2) is C.sub.1 -C.sub.13 alkylene with the proviso that the summation of carbon atoms in (alk.sub.1) plus (alk.sub.2) is not greater than 13; each of m and n is 0 or 1; and W is H, pyridyl, phenyl, fluorophenyl or chlorophenyl; intermediates therefor and methods for their preparation and use.

1,9-Dihydroxyoctahydrophenanthrenes and intermediates therefor

Compounds of the formula ##STR1## wherein R.sub.1 is hydrogen, benzyl, benzoyl, alkanoyl of 1 to 5 carbon atoms or --CO--(CH.sub.2).sub.p --NR'R' wherein p is 0 or an integer from 1 to 4; each of R' and R' when taken individually is hydrogen or alkyl of 1 to 4 carbon atoms; R' and R' when taken together with the nitrogen to which they are attached form a 5- or 6-membered heterocyclic ring selected from piperidino, pyrollo, pyrrolidino, morpholino and N-alkylpiperazino having from 1 to 4 carbon atoms in the alkyl group; R.sub.2 is selected from hydrogen, alkanoyl of 1 to 6 carbon atoms and benzoyl; R.sub.3 is selected from hydrogen, methyl and ethyl; R.sub.4 is selected from hydrogen, alkyl of 1 to 6 carbon atoms and benzyl; Z is selected from: (a) alkylene having from one to nine carbon atoms; (b) -(alk.sub.1).sub.m -X-(alk.sub.2).sub.n - wherein each of (alk.sub.1) and (alk.sub.2) is alkylene having from 1 to 9 carbon atoms, with the proviso that the summation of carbon atoms in (alk.sub.1) plus (alk.sub.2) is not greater than 9; m and n are each 0 or 1; X is selected from O, S, SO and SO.sub.2 ; and W is selected from hydrogen, methyl, pyridyl, piperidyl, phenyl, monochlorophenyl, monofluorophenyl and ##STR2## wherein W.sub.1 is selected from hydrogen, phenyl, monochlorophenyl and monofluorophenyl; a is an integer from 1 to 5 and b is 0 or an integer from 1 to 4, with the proviso that the sum of a and b is not greater than 5. Compounds I and II are useful as analgesics. Compound III is useful as an intermediate for the preparation of Compounds I and II. Intermediates for the preparation of I, II and III are disclosed. A process for the use of compounds I and II to produce analgesia is also described.

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Groton, CT, United States of America

Thomas H Althuis