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
1994-08-30
Cintins, Marianne M.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514332, 514335, 514336, 514351, 546256, 546261, 546263, 546268, 546283, 546284, 546300, 546331, C07D21316, C07D21318, C07D40102, A61K 3144
Patent
active
053428480
DESCRIPTION:
BRIEF SUMMARY
This invention relates to new therapeutically useful thioformamide derivatives, to processes for their preparation and to pharmaceutical compositions containing them.
The new thioformamide derivatives of the present invention are those compounds of formula (I), hereinafter depicted wherein: quinolin-4-yl, optionally substituted by an alkyl or alkoxy group, or a halogen atom; optionally substituted by one or more substituents selected from halogen atoms; hydroxy, alkyl, C.sub.2-4 -alkenyl, alkoxy, phenoxy, tetrahydropyranyloxy, alkanoyl, benzoyl, cyano, nitro, trifluoromethyl, carboxy, amino, (optionally hydroxy)alkylamino, di(optionally hydroxy)alkylamino, trialkylammonio, alkoxycarbonylamino, alkanoylamino, benzoylamino, alkanoyloxy and alkoxycarbonyl groups, and carbamoyl groups (unsubstituted or substituted by one or two alkyl groups in turn optionally substituted by hydroxy groups, or by a straight- or branched-chain divalent group containing from 4 to 6 atoms in the chain and which may contain a further heteroatom so as to form, for example, piperazinocarbonyl or piperidinocarbonyl groups); or atoms), alkenyl group (containing from 2 to 6 carbon atoms) or cycloalkyl group (containing from 3 to 6 ring carbon atoms), each of which may be optionally substituted by one or more substituents selected from halogen atoms; phenyl, naphthyl, imidazolyl and pyridyl groups (each optionally substituted as defined for phenyl, pyridyl, furyl or thienyl groups in a) above); hydroxy, C.sub.2-4 -alkenyl, alkoxy, phenoxy, tetrahydropyranyloxy, alkanoyl, benzoyl, cyano, nitro, carboxy, amino, (optionally hydroxy)alkylamino, di(optionally hydroxy)alkylamino, trialkylammonio, alkoxycarbonylamino, alkanoylamino, benzoylamino, alkanoyloxy and alkoxycarbonyl groups; and carbamoyl groups (unsubstituted or substituted by one or two alkyl groups in turn optionally substituted by hydroxy groups, or by a straight- or branched-chain divalent group containing from 4 to 6 atoms in the chain and which may contain a further heteroatom so as to form, for example, piperazinocarbonyl or piperidinocarbonyl groups); and, unless otherwise specified, contain one to four carbon atoms;
Particularly important classes of compounds of formula (I) exhibit one of more of the following features: acceptable salts.
The presence of a carbonyloxy group on the ring creates an isomeric center in the molecule which in association with the adjacent asymmetric ring carbon atom leads to 4 stereoisomers which, optionally, can be separated into 2 racemic pairs. The racemic pair and enantiomers in which the --OCOX and --CSNHR groups are in the trans relationship are preferred.
In certain cases the substituents A, X, and R can also contribute to stereoisomerism. All such forms are also embraced by the present invention.
A particularly important compound of the present invention is: (.+-.)-trans-2-benzoyloxy-N-methyl-1-(pyrid-4-yl)cyclohexanecarbothioamide thereof.
The letter A is allocated to the compound 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: cardiovascular disorders such as congestive heart failure, and conditions associated with tissue ischaemia such as angina, peripheral vascular disease and cerebrovascular disease; obstruction and asthma; and uterus, including peptic ulcers, irritable bowel syndrome and diverticular disease; and premature labor.
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 Tests
The test methods used were adapted from those described by Winslow et al [Eur. J. Pharmaco
REFERENCES:
patent: 5246950 (1993-09-01), Hart
Winslow et al., European Journal of Pharmacology, 131 (1986) pp. 219-228.
Karaki, H., J. Pharmacol. Methods, 18 (1987) pp. 1-21.
Hart Terance W.
Vacher Bernard Y. J.
Cintins Marianne M.
Nicholson James A.
Parker III Raymond S.
Rhone-Poulenc Rorer Limited
Savitzky Martin F.
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