Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1997-07-03
2000-03-28
Gerstl, Robert
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
544368, 546 64, 546271, 548149, 548151, C07D51304
Patent
active
060433736
DESCRIPTION:
BRIEF SUMMARY
FIELD OF THE INVENTION
The present invention is related to new thiazole derivatives or their pharmaceutically acceptable salts useful as anti-ulcer agents, and to a method for producing them.
BACKGROUND OF THE INVENTION
It has been reported that the gastrointestinal ulcers may be caused by a excessive secretion of acids such as hydrochloride acid or pepsin as well as by an action of anti-inflammatory agents such as indomethacin, toxic chemicals, pathogenic virus or toxic microorganisms. In particular, it had been reported that H.sup.+ /K.sup.+ ATPase, an enzyme which plays an important role during the last step of the acid secretion in stomach cell affects the gastric acidity (Am. J. Physiol., 1983, 245, G589, J. Biol. Chem., 1976, 251, 7690). Therefore, if a compound has an inhibitory activity against the enzyme so that it can be used to suppress gastric acid secretion and treat gastric ulcers.
JP 82-134417A and KR 91-7679A disclose some thiazole derivatives having anti-ulcer activity, and JP 81-5538A and U.S. Pat. No. 4,283,408 teach thiazole derivatives having an activity of suppressing the secretion of gastric juices.
However, there has been still a need to develop agents which are capable of reinforcing various defensive factors against the above described factors causing gastrointestinal ulcers.
The present inventors made extensive researches to provide novel compounds which can effectively inhibit H.sup.+ /K.sup.+ ATPase. And a result thereof, they found out that the compounds represented by the general formula (I) given below showed not only a potent inhibitory activity against H.sup.+ /K.sup.+ ATPase so that they can suppress the secretion of the gastric juices but also a significant cell protecting activity.
SUMMARY OF THE INVENTION
Therefore, an object of the present invention is to provide new thiazole derivatives represented by the following general formula (I): ##STR2## wherein, R is hydrogen atom, a hydroxy group, a straight or branched C.sub.1 -C.sub.6 lower alkyl group, a C.sub.1 -C.sub.4 lower alkoxy group, phenyl group, a phenyl group having one to three substituents selected from a group consisting of a C.sub.1 -C.sub.4 lower alkyl group, a C.sub.1 -C.sub.4 lower alkoxy group, fluorine, chlorine, bromine and an amino group, a C.sub.1 -C.sub.5 alkylphenyl group, a phenyl group having one to three substituents selected from a group consisting of a C.sub.1 -C.sub.4 lower alkyl group, a C.sub.1 -C.sub.4 lower alkoxy group, fluorine, chlorine, bromine and an amino group, a substituted or unsubstituted guanidino group, or an amino group having a general formula: NR.sub.3 R.sub.4 in which R.sub.3 and R.sub.4 identical to or different from each other, represent independently a hydrogen atom, a C.sub.1 -C.sub.6 lower alkyl group, a C.sub.3 -C.sub.6 cycloalkyl group, a substituted or unsubstituted pyridyl group, a phenyl group having one to three substituents selected from a group consisting of a C.sub.1 -C.sub.4 lower alkyl group, a C.sub.1 -C.sub.4 lower alkoxy group, a halogen atom, an amino group, a cyano group and a nitro group, a piperidine group or C.sub.1 -C.sub.4 alkylpiperidine group; independently a hydrogen atom, a hydroxy group, a C.sub.1 -C.sub.6 lower alkyl group, phenyl group, a phenyl group having one substituent selected from a group consisting of a C.sub.1 -C.sub.4 lower alkyl group, a C.sub.1 -C.sub.4 lower alkoxy group, a halogen atom, a nitro and a cyano group, a C.sub.1 -C.sub.5 alkylphenyl group, or a pyridine group; other, are independently a hydrogen atom, a hydroxy group, a C.sub.1 -C.sub.4 lower alkyl group, a C.sub.1 -C.sub.4 lower alkoxy group, phenyl group, or a phenyl group substituted with a C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.4 alkoxy group or a halogen atom, or a C.sub.1 -C.sub.3 alkylphenyl group; 12-membered unsaturated fused cyclic group, said monocyclic and fused cyclic group being comprises of one or more hetero atoms selected from oxygen, oxidative nitrogen and oxidative sulfur atom,
According to the present invention, a method for produc
REFERENCES:
patent: 4283408 (1981-08-01), Hirata et al.
Babu C.A. vol. 111(1) 7296v 1989.
Smolka et al., "Monoclonal antibodies against gastric H.sup.+ +K.sup.+ ATPase", American Physiological Society, 1983, 245, G589-G596.
Sachs et al., "A Nonelectrogenic H.sup.+ Pump in Plasma Membranes of Hog Stomach", The Journal of Biological Chemistry, 1976, 251, 7690-7698.
Fiske et al., "The Colorimetric Determination of Phosphorus", The Journal of Biological Chemistry, 1925, 66, 375-440.
Brezin et al., "Survival Following Massive Resection of Small and Large Bowel; Water, Electrolyte and Blood Volume Studies", Gastroenterology, 1954, 26, 895-905.
Saccomani et al., Biochimica et Biophysica Acta, 1977, 465, 311-330.
Remers et al., J. Heterocycl. Chem., 1975, 12(2), 421-422.
Chai Jun Pyo
Chang Man Sik
Choi Wahn Soo
Chun Jae Kwang
Chung Kae Jong
Gerstl Robert
Yungjin Pharmaceutical Co., Ltd.
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