Prostanoid compounds and pharmaceutical compositions
AssigneeGlaxo Group Limited
InventorsEric W. Collington, Harry Finch, Roger F. Newton
Life of this patent
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Abstract
Prostanoid compounds are described having the formula: ##STR1## where A is a cyclopentane ring, which is substituted by oxo and/or hydroxy or etherified hydroxy and may be saturated or unsaturated; X is --CH.dbd.CH--or --(CH.sub.2).sub.2 --; R is alkyl having a terminal --COOH or ester group; and Y is amino or substituted amino, particularly heterocyclic amino. The compounds have bronchodilator activity and/or inhibit blood platelet aggregation. The preparation and pharmaceutical formulation of the compounds is also described.
Claims12
Prostanoids of the general formula (1) ##STR297## in which A represents ##STR298## X is cis or trans --CH.dbd.CH-- or --(CH.sub.2).sub.2 --;
- R.sup.1 is straight or branched C.sub.1-7 alkyl bearing as a terminal substituent --COOR.sup.10 where R.sup.10 is a hydrogen atom, C.sub.1-6 alkyl or C.sub.7-10 phenalkyl;
- Y represents:
- (i) --NR.sup.2 R.sup.3, where R.sup.2 and R.sup.3 are the same or different and represent hydrogen atom, phenalkyl having a C.sub.1-7 alkyl portion, or C.sub.1-10 alkyl (said C.sub.1-7 alkyl portion or said C.sub.1-10 alkyl being optionally substituted by one or more substituents --OR.sup.7 or NR.sup.8 R.sup.9 ;
- wherein R.sup.7 represents hydrogen atom, C.sub.1-7 alkyl, phenyl or phenalkyl having a C.sub.1-4 alkyl portion;
- and wherein R.sup.8 and R.sup.9 are the same or different and represent hydrogen atom or C.sub.1-4 alkyl, or where --NR.sup.8 R.sup.9 is a saturated heterocyclic amino group as defined below for Y);
- any phenyl group in R.sup.2 or R.sup.3 being optionally substituted by one or more C.sub.1-4 alkyl or trifluoromethyl groups;
- always provided that the total numbers of carbon atoms in the group --NR.sup.2 R.sup.3 does not exceed 15;
- or
- (ii) a saturated heterocyclic amino group selected from the group consisting of pyrrolidino, piperidino, morpholino, piperazino, thiamorpholino, 1-dioxothiamorpholino, homomorpholino, hexamethyleneimino, piperazino substituted at the second nitrogen atom by C.sub.1-7 alkyl or phenalkyl having a C.sub.1-4 alkyl portion, and piperidino which contains in the ring the group >C(OH)R.sup.6 (where R.sup.6 is a hydrogen atom, C.sub.1-7 alkyl, phenyl, or phenalkyl having a C.sub.1-4 alkyl portion) and any of said groups substituted on the ring by one or more C.sub.1-4 alkyl groups;
- R.sup.4 is a hydrogen atom, C.sub.1-6 alkyl (optionally interrupted by one or two oxygen atoms), C.sub.3-6 alkenyl, C.sub.2-4 alkanoyl, phenalkanoyl having a C.sub.2-4 alkanoyl portion, phenyl or aralkyl selected from the group consisting of benzyhydryl, naphthyl (C.sub.1-3) alkyl and phen (C.sub.1-3) alkyl and any one of said aryl groups substituted by one or more halogen, hydroxy C.sub.1-6 alkyl, C.sub.1-6 alkoxy, C.sub.1-4 hydroxyalkoxy, trifluoromethyl, cyano, phenyl, phenoxy, C.sub.5-7 cycloalkyl, phenalkoxy, dimethylaminomethyl, carboxamido (--CONH.sub.2), thiocarboxamido (--CSNH.sub.2), C.sub.1-4 alkanoyl or --NR.sup.8 R.sup.9 groups as defined above);
- R.sup.5 is as defined above for R.sup.4, excluding phenyl and with the proviso that R.sup.5 is not hydrogen when A is the group (h);
- and the physiologically acceptable salts thereof;
- provided that when A is the group (C), then Y is the group--NR.sup.2 R.sup.3.
Dependencies are inferred from the claim text.