Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1990-10-26
1992-04-14
Shen, Cecilia
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514253, 514284, 514285, 514290, 514291, 544257, 544296, 544361, 546 15, 546 80, 546 89, 546 93, 546101, 546286, 546323, A61K 31495, A61K 3144, A61K 31445, C07D48700
Patent
active
051048760
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
The present invention relates to certain benzopyrido piperidine, piperazine and piperidylidene compounds, compositions and methods of use.
The following references have disclosed oxygen or sulfur in the bridgehead of the three ring portion of the molecule:
Canadian Application 780,443, published in the name of Sandoz Patents Ltd.;
Eire 17764, published Apr. 5, 1964 in the name of Sandoz Patents Ltd.;
European Patent Application 81816337.6, Sandoz A.G., published Mar. 10, 1982;
Belgian Application 638,971, Sandoz S.A., published Apr. 21, 1964;
Belgian Application 644,121, Sandoz S.A., published Aug. 20, 1964;
U.S. Pat. No. 4,609,664, issued to Hasspacher on Sept. 2, 1986;
U.S. Pat. No. 3,966,944, issued to Carter on June 29, 1976;
U.S. Pat. No. 3,803,153, issued to Villani on Apr. 9, 1974;
U.S. Pat. No. 3,803,154, issued to Drukker on Apr. 9, 1974;
U.S. Pat. No. 3,325,501, issued to Ettinsen et al. on June 13, 1967;
None of the references disclose substitution on the piperidylidene, piperidine or piperazine nitrogen similar to that set forth below.
SUMMARY OF THE INVENTION
Compounds represented by the structural formula I ##STR2## or a pharmaceutically acceptable salt or solvate thereof, wherein:
one of a, b, c and d represents nitrogen or --NR.sup.11 --, where R.sup.11 is --O.sup.-, --CH.sub.3 or --(CH.sub.2).sub.p CO.sub.2 H where p is 1 to 3, and the remaining a, b, c and d groups are CH which may be substituted with R.sup.1 or R.sup.2 ;
R.sup.1 and R.sup.2 may be the same or different and each independently represents halo, --CF.sub.3, --OR.sup.10, --C(O)R.sup.10, --S(O).sub.e R.sup.12 where e is 0, 1 or 2, --N(R.sup.10).sub.2, --NO.sub.2, SH, CN, --OC(O)R.sup.10, --CO.sub.2 R.sup.10, --OCO.sub.2 R.sup.12, --NR.sup.10 C(O)R.sup.10, alkyl, alkenyl or alkynyl, which alkyl or alkenyl groups may be substituted with halo, --OR.sup.10 or --CO.sub.2 R.sup.10, or R.sup.1 and R.sup.2 may together form a benzene ring fused to the pyridine ring;
R.sup.10 represents H, alkyl or aryl;
R.sup.12 represents alkyl or aryl;
R.sup.3 and R.sup.4 may be the same or different and each independently represents H or any of the substituents of R.sup.1 and R.sup.2, or R.sup.3 and R.sup.4 may be taken together to represent a saturated or unsaturated C.sub.5 -C.sub.7 ring fused to the benzene ring;
R.sup.5, R.sup.6, R.sup.7 and R.sup.8 each independently represents H, --CF.sub.3, --CO.sub.2 R.sup.10, --C(O)R.sup.10, alkyl or aryl, which alkyl or aryl may be substituted with --OR.sup.10, --SR.sup.10, --N(R.sup.10).sub.2, --NO.sub.2, --C(O)R.sup.10, --OC(O)R.sup.12, --OCO.sub.2 R.sup.12, --CO.sub.2 R.sup.10 and --OPO.sub.3 (R.sup.10).sub.2, or one of R.sup.5, R.sup.6, R.sup.7 and R.sup.8 may be taken in combination with R as defined below to represent --(CH.sub.2).sub.r --where r is 1 to 4, said combination being optionally substituted with lower alkyl, lower alkoxy, --CF.sub.3 or aryl, or R.sup.5 may be combined with R.sup.6 to represent .dbd.O or .dbd.S, and/or R.sup.7 may be combined with R.sup.8 to represent .dbd.O or .dbd.S;
T represents carbon or nitrogen, with the dotted line attached to T representing an optional double bond when T is carbon;
m and n are integers 0, 1, 2, or 3, such that the sum of m plus n equals 0 to 3;
when m plus n equals 1, X represents --O--, --S(O).sub.e --where e is 0, 1 or 2, --NR.sup.10 --, --C(O)NR.sup.10 --, --NR.sup.10 C(O)--, --C(S)NR.sup.10 --, --NR.sup.10 C(S)--, --CO.sub.2 --or --O.sub.2 C--, where R.sup.10 is as defined above;
when m plus n equals 2, X represents --O--, --S(O).sub.e --where e is 0, 1 or 2, or --NR.sup.10 ;
when m plus n represents 0, X can be any substituent for m plus n equalling 1 and X can also be a direct bond, cyclopropylene or propenylene;
when m plus n equals 3 then X equals a direct bond;
each R.sup.a may be the same or different, and each independently represents H, lower alkyl or phenyl;
Z represents .dbd.O, .dbd.S or .dbd.NR.sup.13 with R.sup.13 equal to R.sup.10 or --CN, wherein R.sup.10 is as defined above, such that
(a) when Z i
REFERENCES:
patent: 3325501 (1967-06-01), Ettingen et al.
patent: 3803154 (1974-04-01), Drukker
patent: 3966944 (1976-06-01), Carter
patent: 4609664 (1986-09-01), Hasspacher
Ganguly Ashit K.
Green Michael J.
Piwinski John J.
Villani Frank J.
Wong Jesse K.
Schering Corporation
Shen Cecilia
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