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US 4,057,547 AGranted
Azabicyclic compounds, and production thereof
AssigneeOrtho Pharmaceutical Corporation
InventorsSeymour Levine, Vinayak V. Kane
Life of this patent
Estimating the term…
Abstract
Novel azabicyclic compounds useful for their central nervous system depressant and cardiovascular activity, methods for preparing same, and intermediates.
Claims28
A compound having the formula:
- ##STR15## wherein:
- A is a member selected from the group consisting of ##STR16## R.sub.1 is a member selected from the group consisting of loweralkyl, phenyl, substituted phenyl wherein the substituent is 1-3 groups selected from loweralkyl, loweralkoxy, halo and amino, phenyl loweralkyl, substituted phenyl loweralkyl wherein the substituent is 1-3 groups selected from loweralkyl, loweralkoxy, halo and amino, loweralkylaminodophenyl, and heterocyclic aryl selected from pyridyl, quinolyl, imidazolyl, pyrazinyl, pyrrolyl, thienyl, thiazolyl, thiadiazolyl, pyrazolyl, triazolyl, oxazolyl and pyrimidinyl;
- R.sub.2 -r.sub.5 are each members selected from the group consisting of hydrogen, halo, cyano, COOR', CONR'R", CH.sub.2 NR'R", OR'", loweralkyl, phenyl, substituted phenyl wherein the substituent is 1-3 groups selected from loweralkyl, loweralkoxy, halo and amino, phenyl loweralkyl, and substituted phenyl loweralkyl wherein the substituent is 1-3 groups selected from loweralkyl, loweralkoxy, halo and amino, said R' and R" each being a member selected from the group consisting of hydrogen and loweralkyl and said R'" being a member selected from the group consisting of hydrogen, loweralkyl, phenyl and substituted phenyl wherein the substituent is 1-3 groups selected from loweralkyl, loweralkoxy, halo and amino;
- R.sub.6 is a member selected from the group consisting of loweralkyl, phenyl, and substituted phenyl wherein the substituent is 1-3 groups selected from lowerakyl, loweralkoxy, halo and amino;
- and
- R.sub.7 and R.sub.8 are each members selected from the group consisting of hydrogen, halo, loweralkyl, loweralkoxy, and amino;
- and
- pharmaceutically acceptable quaternary salts thereof wherein R.sub.1 is pyridyl, quinolyl, imidazolyl, pyrazinyl, pyrrolyl, thiazolyl, thiadiazolyl, pyrazolyl, triazolyl, oxazolyl or pyrimidinyl.
5 more elements
A compound having the formula:
- ##STR17## wherein:
- R.sub.1 is a member selected from the group consisting of loweralkyl, phenyl, substituted phenyl wherein the substituent is 1-3 groups selected from loweralkyl, loweralkoxy, halo and amino, phenyl loweralkyl, substituted phenyl loweralkyl wherein the substituent is 1-3 groups selected from loweralkyl, loweralkoxy, halo and amino, loweralkylamidophenyl, and heterocyclic aryl selected from pyridyl, quinolyl, imidazolyl, pyrazinyl, pyrrolyl, thienyl, thiazolyl, thiadiazolyl, pyrazolyl, triazolyl, oxazolyl and pyrimidinyl;
- R.sub.2 -r.sub.5 are each members selected from the group consisting of hydrogen, halo, cyano, COOR', CONR'R", CH.sub.2 NR'R", OR'", loweralkyl, phenyl, substituted phenyl wherein the substituent is 1-3 groups selected from loweralkyl, loweralkoxy, halo and amino, phenyl loweralkyl, and substituted phenyl loweralkyl wherein the substituent is 1-3 groups selected from loweralkyl, loweralkoxy, halo and amino, said R' and R" each being a member selected from the group consisting of hydrogen and loweralkyl and said R'" being a member selected from the group consisting of hydrogen, loweralkyl, phenyl, and substituted phenyl wherein the substituent is 1-3 groups selected from loweralkyl, loweralkoxy, halo and amino;
- and
- R.sub.6 is a member selected from the group consisting of loweralkyl, phenyl, and substituted phenyl wherein the substituent is 1-3 groups selected from loweralkyl, loweralkoxy, halo and amino;
- and
- pharmaceutically acceptable quaternary salts thereof wherein R.sub.1 is pyridyl, quinolyl, imidazolyl, pyrazinyl, pyrrolyl, thiazolyl, thiadiazolyl, pyrazolyl, triazolyl, oxazolyl or pyrimidinyl.
4 more elements
A compound having the formula:
- ##STR18## wherein:
- R.sub.1 is a member selected from the group consisting of loweralkyl, phenyl, substituted phenyl wherein the substituent is 1-3 groups selected from loweralkyl, loweralkoxy, halo and amino, phenyl loweralkyl, substituted phenyl loweralkyl wherein the substituent is 1-3 groups selected from loweralkyl, loweralkoxy, halo and amino, loweralkylamidophenyl, and heterocyclic aryl selected from pyridyl, quinolyl, imidazolyl, pyrazinyl, pyrrolyl, thienyl, thiazolyl, thiadiazolyl, pyrazolyl, triazolyl, oxazolyl and pyrimidinyl;
- R.sub.2 -r.sub.5 are each members selected from the group consisting of hydrogen, halo, cyano, COOR', CONR'R", CH.sub.2 NR'R", OR'", loweralkyl, phenyl, substituted phenyl wherein the substituent is 1-3 groups selected from loweralkyl, loweralkoxy, halo and amino, phenyl loweralkyl, and substituted phenyl loweralkyl wherein the substituent is 1-3 groups selected from loweralkyl, loweralkoxy, halo and amino, said R' and R" each being a member selected from the group consisting of hydrogen and loweralkyl and R'" being a member selected from the group consisting of hydrogen, loweralkyl, phenyl and substituted phenyl wherein the substituent is 1-3 groups selected from loweralkyl, loweralkoxy, halo and amino;
- and
- R.sub.7 and R.sub.8 are each members selected from the group consisting of hydrogen, halo, loweralkyl, loweralkoxy, and amino;
- and
- pharmaceutically acceptable quaternary salts thereof wherein R.sub.1 is pyridyl, quinolyl, imidazolyl, pyrazinyl, pyrrolyl, thiazolyl, thiadiazolyl, pyrazolyl, triazolyl, oxazolyl or pyrimidinyl.
4 more elements
A compound having the formula:
- ##STR19## wherein:
- A' is a member selected from the group consisting of ##STR20## R'.sub.1 is a member selected from the group consisting of loweralkyl, phenyl, substituted phenyl wherein the substituent is 1-3 groups selected from loweralkyl, loweralkoxy, halo and amino, phenyl loweralkyl, substituted phenyl loweralkyl wherein the substituent is 1-3 groups selected from loweralkyl, loweralkoxy, halo and amino, nitrophenyl, and heterocyclic aryl selected from pyridyl, quinolyl, imidazolyl, pyrazinyl, pyrrolyl, thienyl, thiazolyl, thiadiazolyl, pyrazolyl, triazolyl, oxazolyl and pyrimidinyl;
- R.sub.2 -r.sub.5 are each members selected from the group consisting of hydrogen, halo, cyano, COOR', CONR'R", CH.sub.2 NR'R", OR'", loweralkyl, phenyl, substituted phenyl wherein the substituent is 1-3 groups selected from loweralkyl, loweralkoxy, halo and amino, phenyl loweralkyl, and substituted phenyl loweralkyl wherein the substituent is 1-3 groups selected from loweralkyl, loweralkoxy, halo and amino, said R' and R" each being a member selected from the group consisting of hydrogen and loweralkyl and said R'" being a member selected from the group consisting of hydrogen, loweralkyl, phenyl, and substituted phenyl wherein the substituent is 1-3 groups selected from loweralkyl, loweralkoxy, halo and amino;
- R.sub.6 is a member selected from the group consisting of loweralkyl, phenyl and substituted phenyl wherein the substituent is 1-3 groups selected from loweralkyl, loweralkoxy, halo and amino;
- and
- R'.sub.7 and R'.sub.8 are each members selected from the group consisting of hydrogen, halo, loweralkyl, loweralkoxy, amino, and nitro.
3 more elements
Dependencies are inferred from the claim text.