Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1993-03-30
1995-11-14
Trang, Cecilia
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514252, 514321, 514326, 514328, 544295, 544368, 544379, 546198, 546209, 546212, 546213, C07D40900, C07D41900, C07D41100, A61K 31495, A61K 31445
Patent
active
054666910
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
This is a 371 application of PCT/JP92/01002, filed Aug. 5, 1992.
The present invention relates to novel thiophene compounds useful as pharmaceuticals and their pharmaceutically acceptable salts.
BACKGROUND ART
Up to the present, there have been developed a large number of psychotropic agents for the therapy of anxiety neurosis, schizophrenia, depression, etc. Yet, most of these drugs accompany various side-effects upon continuous administration, or the like, such as excessive sedation, addiction, dyskinesia and Parkinson disease, and they are not entirely satisfactory.
Meanwhile, Tetrahedron 44(18), 5921-5928 (1988) teaches methods for synthesizing 5-acetyl-3-cyano-2-(2-diethylaminoethyl)thio-4-phenylthiophene and 5-benzoyl-4-chloro-3-cyano-2((2-dimethylaminoethyl)thio)thiophene. Eur. J. Med. Chem. Chim. Ther. 12(6), 557-563 (1977)teaches 2-((2-piperidinoethyl)thio)thiophene, 2-((2-morpholinoethyl)thio)thiophene, and others having an antiviral activity. Japanese Patent Unexamined Publication No. 133989/1977 discloses compounds such as 1-[2-(2thienylthio)ethyl]-4-(N-phenyl-N-propionylamino)piperidine having a hypotensive action. Japanese Patent Unexamined Publication No. 81582/1981 discloses N-[3-[[5-(dimethylamino)- methyl-4-methyl-2-thienyl]thio]propyl]-isoindole-l,3(2H)-dione as a synthetic intermediate of a compound having a histamine H.sub.2 antagonistic action. Also, Chemical Abstracts 112(9): 77137p shows N-[2-(2-thienylthio)ethyl]-2-oxo-5-hydroxypyrrolidine. However, there have not been reported action of these compounds on the central nervous system.
Japanese Patent Unexamined Publication No. 115568/1985 discloses methyl (2RS, 5R)-3-[2-(5-carbamoyl-2-thienyl)ethyl]-5-phenyl-2 oxazolidinecarboxylate having an antidiabetic effect. Japanese Patent Unexamined Publication No. 213278/1989 discloses 1-[2-(2-thienyl)ethyl]-4-(2-ethyl-1,3,4-oxadiazol-5-yl)-4-(N-phenylpropion amido)piperidine having an analgesic action. Yakugaku Zasshi 104(6), 680-690 (1984) reports 3-[2-(5-acetyl-2-thienyl)ethyl]-2,4-oxazolidincdione, etc. having an antiulcer action. Furthermore, Japanese Patent Unexamined Publication Nos. 185777/1985 and 45381/1989, US Patent No. 4032531, Japanese Patent Unexamined Publication Nos. 151183/1977, 93334/1974 and 40582/1975, US Patent No. 3919243, Japanese Patent Examined Publication No. 14557/1967, U.S. Pat. No. 3171838, UK Patent No. 1294720, and Japanese Patent Unexamined Publication Nos. 85576/1973, 85578/1973 and 206558/1983 disclose thiophene compounds. However, these compounds have not been reported as having an action on central nervous system.
As a compound having a psychotropic action, Japanese Patent Unexamined Publication No. 156879/1977 reports 4-2-(4- acetylaminomethylphenyl)ethyl-1-phenylpiperazine.
DISCLOSURE OF THE INVENTION
The present inventors have made intensive studies with the aim of developing a psychotropic agent having less side-effects and found a novel thiophenc compound exhibiting superior actions, which resulted in the completion of the invention.
That is, the present invention relates to:
1. a thiophene compound of the formula ##STR2## wherein;
R.sup.1 and R.sup.2 are the same or different, and each is a hydrogen, a halogen, a nitro, an amino, a cyano, an alkyl, a mono- or di-substituted amino, a formyl, -COOR.sup.3 (R.sup.3 is a hydrogen, an alkyl or an ester residue hydrolyzablc in the body), an alkoxy, a hydroxyalkyl, a haloalkyl, a haloalkoxy, an alkanoyl, an aroyl, an arylalkanoyl, an alkanoyloxyalkyl, an aroyloxyalkyl, a formylamino, an alkanoylamino, an arylalkanoylamino, an aroylamino, a formylaminoalkyl, an alkanoylaminoalkyl, a haloalkanoylaminoalkyl, an arylalkanoylaminoalkyl, an aroylaminoalkyl, an arylalkyl, a carbamoyl, a mono- or di-substituted carbamoyl, a carbamoylalkyl, a mono- or di-substituted carbamoylalkyl, an aminoalkyl, a mono- or di-substituted aminoalkyl, an alkylsulfonylaminoalkyl, a hydroxyiminoalkyl or an alkoxyiminoalkyl;
X is -S(O).sub.n - (n is 0, 1 or 2), -CO-, -CH(OR.sup.10)- (R.sup.10 is a hydrogen, an alk
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J. M. Luteijn et al, Tetrahedro vol. 44, No. 18, pp. 5921-5928 (1988).
Morimoto Yasuto
Nakao Tohru
Obata Minoru
Ono Yuji
Tanaka Hiroshi
Trang Cecilia
Yoshitomi Pharmaceutical Industries Ltd.
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