Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1992-08-07
1994-01-04
Ivy, C. Warren
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
546332, 564271, 514641, C07D21353
Patent
active
052760464
DESCRIPTION:
BRIEF SUMMARY
This invention relates to new therapeutically useful hydrazine derivatives, to processes for their preparation and to pharmaceutical compositions containing them.
The new hydrazine derivatives of the present invention are those compounds of formula (I), hereinafter depicted wherein:
A represents:
(1) a phenyl or naphthyl group which is optionally substituted by one or more substituents selected from halogen atoms and alkyl, aryl, arylalkyl, cyano, nitro, trifluoromethyl, carbamoyl, carboxy, alkoxycarbonyl and alkylsulphonyl groups; or
(2) a heteroaromatic group containing 1 or 2 nitrogen atoms, selected from pyrid-3-yl, quinolin-3-yl, isoquinolin-4-yl, pyridazin-4-yl, pyrimidin-5-yl, pyrazin-3-yl, indol-3-yl and thiazol-5-yl, optionally substituted by one or more substituents selected from alkyl and alkoxy groups and halogen atoms; and
R.sup.1 represents either:
i) a hydrogen atom;
ii) an alkyl group which is unsubstituted or substituted by one or more substituents selected from C.sub.2-4 -alkenyl, carboxy, alkoxycarbonyl, hydroxy, alkoxy, amino, alkylamino and dialkylamino groups, and from carbamoyl groups which may be unsubstituted or substituted by one or two alkyl groups; or
iii) a benzyl, phenethyl, 1-naphthylmethyl, 2-naphthylmethyl or pyrid-3-ylmethyl group, each of which may be substituted on the ring by one or more substituents selected from halogen atoms and hydroxy, alkyl, cyano, nitro, trifluoromethyl, carboxy, alkylamino, alkanoylamino and alkoxycarbonyl groups and from alkoxy groups (which themselves are unsubstituted or substituted by one or more substituents selected from C.sub.2-4 -alkenyl, carboxy, alkoxycarbonyl, hydroxy, alkoxy, amino, alkylamino and dialkylamino groups, and from carbamoyl groups which may be unsubstituted or substituted by one or two alkyl groups); and pharmaceutically acceptable salts thereof.
In this specification all alkyl groups and alkyl moieties can be straight-chain or branched, and, unless otherwise specified, contain one to about four carbon atoms; and all aryl groups and aryl moieties, unless otherwise specified, are preferably phenyl or naphthyl groups which may be substituted by one or more substituents selected from alkyl and alkoxy groups and halogen atoms.
A preferably represents a heteroaromatic group as hereinbefore defined, preferably a pyrid-3-yl group, R.sup.1 preferably represents a benzyl group and the oxyimino group is preferably in the anti-configuration.
In certain cases the substituents A and R.sup.1 can contribute to stereoisomerism. All such forms are embraced by the present invention.
A particularly important compound of the present invention is: dihydrochloride
The letter A is allocated for ease of reference in other parts of the specification.
The compounds have valuable pharmacological properties, in particular properties which are indicative of utility in the treatment and/or prophylaxis of disorders associated with:
(1) vascular smooth muscle contraction including hypertension and other cardiovascular disorders such as congestive heart failure, and conditions associated with tissue ischaemia such as angina, peripheral vascular disease and cerebrovascular disease;
(2) respiratory smooth muscle contraction including reversible airways obstruction and asthma;
(3) contraction of smooth muscle of gastrointestinal tract, urinary bladder and uterus, including peptic ulcers, irritable bowel syndrome and diverticular disease; and premature labour.
The compounds also have utility in the inhibition of head hair loss associated with male pattern baldness, by topical application.
Compounds within the scope of the present invention exhibit positive pharmacological activities as demonstrated by tests which are believed to correlate to pharmacological activity in humans and other animals.
For example, compounds of general formula (I) were submitted to:
Vaso-relaxant Activity Test
The test method used was adapted from those described by Winslow et al [Eur. J. Pharmacol., 131, 219-228 (1986)] and Karaki [J. Pharmacol. Methods, 18, 1-21 (1987)] for di
Hart Terance W.
Sharp Brian W.
Walsh Roger J. A.
Davis Zinna N.
Ivy C. Warren
Nicholson James A.
Parker III Raymond S.
Rhone-Poulenc Rorer Limited
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