Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1993-09-27
1995-08-08
Dentz, Bernard
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
546113, A61K 31435, C07D47104
Patent
active
054399173
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/SE92/00190.
FIELD OF THE INVENTION
The object of the present invention is to provide novel compounds, and therapeutically acceptable salts thereof, which inhibit exogenously or endogenously stimulated gastric acid secretion and thus can be used in the prevention and treatment of peptic ulcer.
The present invention also relates to the use of the compounds of the invention for inhibiting gastric acid secretion in mammals including man. In a more general sense, the compounds of the invention may be used for prevention and treatment of gastrointestinal inflammatory diseases, and gastric acid-related diseases in mammals including man, such as gastritis, gastric ulcer, duodenal ulcer, reflux esophagitis and Zollinger-Ellison syndrom. Furthermore, the compounds may be used for treatment of other gastrointestinal disorders where gastric antisecretory effect is desirable e.g. in patients with gastrinomas, and in patients with acute upper gastrointestinal bleeding. They may also be used in patients in intensive care situations, and pre- and postoperatively to prevent acid aspiration and stress ulceration, The invention also relates to pharmaceutical compositions containing at least one compound of the invention, or a therapeutically acceptable salt thereof, as active ingredient. In a further aspect, the invention relates to processes for preparation of such new compounds, and to the use of the active compounds for the preparation of pharmaceutical compositions for the medical use indicated above.
PRIOR ART
Certain pyrrolo[2,3-b]pyridines have been disclosed in Sally Pak.J. Pharmacol. 86 Vol 2(2) pp 43-36 (1985), Saify, J. Pharm. Univ. Kar. 2(2):99-103 (1984), TimPe et al. J. Prakt. Chem. 80 Vol 322(3) pp 517-21 (1980) Ogali et al., Indian Journal of Chemistry Vol. 27B, 656-651 (1988).
THE INVENTION
It has been found that compounds of the following formula I are effective as inhibitors of gastric acid secretion. The compounds of the formula I exert this effect by inhibiting the gastrointestinal H.sup.+ K.sup.+ -ATPase enzyme.
The compounds of the invention are of the following formula I: ##STR2## or a pharmaceutically acceptable salt thereof, wherein X represents ##STR3## or --CH.sub.2 --; R.sup.1 represents H, lower alkyl, CH.sub.2 --O--R.sup.7 halogen phenyl or phenyl substituted with (1-6c) alkyl, (1-6c) alkoxy, (1-6c) acyl, halogen, CF.sub.3, CN, NH.sub.2, NO.sub.2 or (1-6c) alkoxycarbonyl; ##STR4## halogen, O--R.sup.8, ##STR5## S--CN, CH.sub.2 OH, CH.sub.2 C.tbd.CH, CF.sub.3,CH.sub.2 NC or NH.sub.2 ; R.sup.3 represents H, lower alkyl, CF.sub.3, O--R.sup.9, NH.sub.2, lower ##STR6## S--R.sup.10 or NHCOR.sup.10 ; R.sup.4 and R.sup.5 which are the same or different represent H lower alkyl, CN, halogen, O--R.sup.11, NO.sub.2, NH.sub.2, lower alkylamino, di-lower alkylamino, S--R.sup.12, NHCOR.sup.13, ##STR7## R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.11, and R.sup.13 which are the same or different, represent H or lower alkyl; alkyl; R.sup.1 and R.sup.2 are not simultaneously H. As used herein, the term "lower" when applied to hydrocarbon groups, alkoxy-, alkylamino-, dialkylamino-, alkylthio, alkylsulfinyl-, phenylalkylthio-, phenylalkylsulfinyl, acylamino- or alkoxycarbonyl groups includes straight and branched chain hydrocarbon group having up to 6 carbon atom.
The term halogen includes fluoro, chloro bromo and iodo.
Both the pure enantiomers, racemic mixtures and unequal mixtures of two enantiomers are within the scope of the present invention. It should be understood that all the diastereomeric forms possible (pure enantiomers or racemic mixtures) are within the scope of the invention. Also included in the invention are derivatives of the compounds of the formula I which have the biological function of the compounds of the formula I.
Depending on the process conditions and the starting materials, the end products of the formula I are obtained either in neutral or salt form. Both the free base or acid and the salts of these end products are within the scope of the inventi
REFERENCES:
Saify, Pakistan J. Pharmacology, vol. 2(2), pp. 43-46 (1985).
Briving Carin
Carlsson Stig
Carter Robert
Elebring Marie
Kuhler Thomas
Aktiebolaget Astra
Dentz Bernard
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