4,5-diaryl oxazole derivatives

Details 4,5-diaryl oxazole derivatives 4,5-diaryl oxazole derivatives

1998-01-21

1999-10-26

Ramsuer, Robert W.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

514374, 546209, 548235, A61K 3142, A61K 31445, C07D26330, C07D41304

Patent

active

059729651

DESCRIPTION:

BRIEF SUMMARY
DESCRIPTION

1. Technical Field
This invention relates to new heterocyclic compounds and pharmaceutically acceptable salts thereof which are useful as a medicament.
2. Background Art
Some heterocyclic compounds have been known as described, for example, in WO 95/17393.


DISCLOSURE OF INVENTION

This invention relates to new heterocyclic compounds. More particularly, this invention relates to new heterocyclic compounds and pharmaceutically acceptable salts thereof which have pharmacological activities such as an inhibitory activity on platelet aggregation, vasodilating activity, antihypertensive activity or the like and are prostaglandin I.sub.2 agonists, to processes for their production, to a pharmaceutical composition containing the same and to a use thereof for manufacture of medicaments.
Accordingly, one object of this invention is to provide new and useful heterocyclic compounds and pharmaceutically acceptable salts thereof.
Another object of this invention is to provide processes for production of the heterocyclic compounds and salts thereof.
A further object of this invention is to provide a pharmaceutical composition containing, as an active ingredient, said heterocyclic compounds or pharmaceutically acceptable salts thereof.
Still further object of this invention is to provide use of the heterocyclic compounds and pharmaceutically acceptable salts thereof for manufacture of medicaments for the therapeutic and/or prophylactic treatment of arterial obstruction, cerebrovascular disease, hepatic cirrhosis, arteriosclerosis, ischemic heart disease, restenosis after percutaneous transluminal coronary angioplasty, hypertension or the like.
The heterocyclic compounds of this invention can be represented by the following formula (I): ##STR1## wherein R.sup.1 is carboxy or protected carboxy,
R.sup.2 is aryl which may have suitable substituent(s),
R.sup.3 is aryl which may have suitable substituent(s),
R.sup.4 is hydrogen, lower alkyl, hydroxy or aryl,
A.sup.1 is lower alkylene, ##STR2##
--A.sup.3 -- is ##STR3## (in which --A.sup.4 -- is bond, --CH.sub.2 -- or --CO--, and ##STR4## is cyclo(C.sub.5 -C.sub.8)alkene, cyclo(C.sub.7 -C.sub.8)alkane, bicycloheptane, bicycloheptene, tetrahydrofuran, tetrahydrothiophene, azetidine, pyrrolidine or piperidine, each of which may have suitable substituent(s)) or --X--A.sup.6 -- [in which --X-- is --O--, --S-- or ##STR5## (in which R.sup.5 is hydrogen, lower alkyl or acyl) and
A.sup.6 is lower alkylene which may have suitable substituent(s)], and
n is 0 or 1.
According to the present invention, the new heterocyclic compounds (I) can be prepared by the processes which are illustrated in the following scheme. ##STR6## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, n, A.sup.1, ##STR7## --A.sup.3 -- and --A.sup.4 -- are each as defined above,
Y.sup.1 is acid residue,
R.sup.1.sub.a is protected carboxy,
R.sup.6 is imino protective group, ##STR8## is cyclo(C.sub.7 -C.sub.8)alkene, ##STR9## is cyclo(C.sub.7 -C.sub.8)alkane, and
Y.sup.2 is halogen.
The starting compounds (II), (V) and (VI) are novel and can be prepared by the following process. ##STR10## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, n, A.sup.1, ##STR11## --A.sup.3 --, --A.sup.4 -- and Y.sup.2 are each as defined above,
R.sup.7 is hydroxy protective group, and
R.sup.8 is acyl.
Suitable pharmaceutically acceptable salts of the object compound (I) are conventional non-toxic salts and include a metal salt such as an alkali metal salt (e.g. sodium salt, potassium salt, etc.) and an alkaline earth metal salt (e.g. calcium salt, magnesium salt, etc.), an ammonium salt, an organic base salt (e.g. trimethylamine salt, triethylamine salt, pyridine salt, picoline salt, dicyclohexylamine salt, N,N'-dibenzylethylenediamine salt, etc.), an organic acid salt (e.g. acetate, maleate, tartrate, methanesulfonate, benzenesulfonate, formate, toluenesulfonate, trifluoroacetate, etc.), an inorganic acid salt (e.g. hydrochloride, hydrobromide, sulfate, phosphate, etc.), a salt with an amino acid (e.g. arginine, aspartic acid, glutamic acid

REFERENCES:
patent: 5348969 (1994-09-01), Romine et al.

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