Organic compounds -- part of the class 532-570 series – Organic compounds – Four or more ring nitrogens in the bicyclo ring system
Patent
1996-05-13
1997-01-14
Ramsur, Robert W.
Organic compounds -- part of the class 532-570 series
Organic compounds
Four or more ring nitrogens in the bicyclo ring system
544361, 546 84, C07D47104
Patent
active
055941400
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention is to imidazo[1,5-a]quinolines which are useful pharmaceutical agents for the treatment of anxiety, sleep disorders, panic states, convulsions and muscle disorders.
EP 283,162 discloses imidazo[1,5-a]quinolines useful as anticonvulsants and anxiolytic agents, wherein only phenyl is attached to the C.sub.5 -position of the quinoline. These compounds lack a carbonyl group at the 5-position. The closest chemically structural compound in EP 283,162 to the present invention is 3-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-5-phenylimidazo[1,5a]quinoline which completely lacks affinity for the benzodiazepine receptor.
J. Her. Chem., 28, 1715 (1991 ) discloses imidazo[1,5-a]quinolines containing esters, acids, or amides at the 3-position. The 5-position is unsubstituted (5-H).
International Publication No. WO92/22552 discloses imidazo[1,5-a]quinoxalines which require a nitrogen atom at the 5-position for the treatment of anxiety and sleep disorders. The compounds of the present invention do not have nitrogen at the 5-position.
U.S. Pat. No. 4,838,925 discloses imidazo[1,5-a]quinoxalines which require a nitrogen atom at the 5-position and which are useful as agricultural chemicals. The compounds of the present invention do not have nitrogen at the 5-position.
Also known are the imidazo[1,2-a]quinolines. However, these compounds represent a different core structure of the 5-membered imidazo ring. Further, they do have a carbonyl at the 5-position. Because of their core structural differences they cannot have an ester, aryl, or oxadiazole groups attached at the 3-position as they contain an imidazole nitrogen at this site.
SUMMARY OF INVENTION
Disclosed are imidazo[1,5-a]quinolines of formula (I) ##STR2## where (I) R.sub.3 is different and are selected from the group consisting of R.sub.3-2 and R.sub.3-3 are taken together with the attached nitrogen atom to form a heterocyclic moiety selected from the group consisting of pyrrolidinyl, morpholinyl, piperazinyl and piperidinyl, ##STR3## where w is 1 or 2 and where R.sub.3-6 is (a) --H, above, above, above, different and are defined above, defined above, different and are --H or C.sub.1 -C.sub.3 alkyl, ##STR4## where R.sub.3-6 is defined above, (3) 3-substituted-1,2,4-oxadiazol-5-yl ##STR5## where R.sub.3-6 is as defined above, (4) 4- or 5-substituted isoxazol-3-yl ##STR6## where w and R.sub.3-6 are defined above, (5) 3- or 4-substituted isoxazol-5-yl ##STR7## where w and R.sub.3-6 are defined above; (II) R.sub.4 is different and are defined above, above, above, defined above, different and are defined above, defined above, and are as defined above, different and are selected from the group consisting of R.sub.5-6 and R.sub.5-7 are taken together with the attached nitrogen atom to form a heterocyclic moiety selected from the group consisting of ##STR8## where m is 1 thru 4, p is 0 thru 4 and R.sub.5-8 is selected from the group consisting of ##STR9## where m and R.sub.5-8 are defined above, (c) ##STR10## where q is 1 or 2, where p and R.sub.5-8 are defined above and where R.sub.5-9 is ##STR11## where m, q, R.sub.5-8 and R.sub.5-9 are defined above, (e) ##STR12## where R.sub.5-8 and R.sub.5-9 are defined above, (f) ##STR13## where m, R.sub.5-8 and R.sub.5-9 are defined above, (IV) R.sub.6 is different and are selected from the group consisting of R.sub.6-2 and R.sub.6-3 are taken together with the attached nitrogen atom to form a heterocyclic moiety selected from the group consisting of pyrrolidinyl morpholinyl, piperazinyl, piperdinyl, above, above, R.sub.6-3 are defined above, defined above, different and are selected from the group consisting of R.sub.6-2 and R.sub.7-3 are taken together with the attached nitrogen atom to form a heterocyclic moiety select from the group consisting of pyrrolidinyl, morpholinyl, piperazinyl, piperdinyl, above, above, R.sub.7-3 are defined above, defined above, useful for the treatment of anxiety, sleep disorders, panic states, convulsions and muscle disorders.
DE
REFERENCES:
patent: 3668208 (1972-06-01), Baxter
Jacobsen Eric J.
TenBrink Ruth E.
Ramsur Robert W.
Stein Bruce
The Upjohn Company
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