Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1995-05-10
1998-02-24
Schofer, Joseph L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
546121, 5462774, 548469, 5483701, 5483157, A61K 31415, C07D47102, C07D20902
Patent
active
057212465
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to a novel sulfonamide or sulfonic ester derivative, a process for the preparation of the derivative, and a drug composition containing the same as an active ingredient.
1. Prior Art
Chemotherapeutic agents which have been used in the treatment of cancers include cyclophosphamide as an alkylating agent; methotrexate and fluorouracil as antimetabolites; adriamycin, mitomycin and bleomycin as antibiotics; vincristine and etoposide as drugs derived from plants; and cisplatin as a metal complex. However, these agents are insufficient in antitumor activity, so that the development of a new antitumor agent is eagerly expected.
Further, 2-sulfanylamidoquinoxaline derivatives (U.S. Pat. No. 4,931,433) and N-(2-anilino-3-pyridinyl)benzenesulfonamide derivatives (EP-A472053) have been reported as aromatic sulfonamide antitumor agents. No report has been made on aromatic sulfonic ester antitumor agents.
2. Disclosure of Invention
The present invention aims at providing a novel sulfonamide or sulfonic ester derivative which exhibits an excellent antitumor activity and is different from the antitumor agents of the prior art in basic skeleton. The present invention also aims at providing a process for the preparation of the derivative and a drug composition containing the same as an active ingredient.
In order to achieve the above aims, the inventors of the present invention have intensively studied to find an excellent antitumor agent. As a result of the studies, they have found that a novel heterobicyclic sulfonamide or sulfonic ester derivative exhibits an excellent antitumor activity and is lowly toxic. The present invention has been accomplished on the basis of this finding.
Namely, the present invention relates to a sulfonamide or sulfonic ester derivative represented by the general formula (I) or a pharmacologically acceptable salt thereof: ##STR2## (wherein A represents a monocyclic or bicyclic aromatic ring which may be substituted, unsaturated heterocycle containing one nitrogen atom as the heteroatom, each of which may be substituted, atoms which may be substituted, represent hydrogen or lower alkyl; with the proviso that (1) the case wherein A is 4-methylbenzene, W is a single bond, X is a group represented by formula --NH--, B is methoxybenzene and C is unsubstituted imidazole and (2) the case wherein A is 4-(acetamido)benzene or 4-aminobenzene, W is a single bond, X is a group represented by formula --NH--, B is unsubstituted benzene and C is unsubstituted pyrazole are excepted.)
Further, the present invention provides the use of the above compound as a drug.
Namely, the present invention also relates to a drug composition comprising a pharmacologically effective amount of a sulfonamide or sulfonic ester derivative or a pharmacologically acceptable salt thereof as set forth in claim 1, and a pharmacologically acceptable carrier; a method for the treatment of a tumor which comprises administering a sulfonamide or sulfonic ester derivative or a pharmacologically acceptable salt thereof as set forth in claim 1 to a patient in a pharmacologically effective dose; and the use of a sulfonamide or sulfonic ester derivative or a pharmacologically acceptable salt thereof as set forth in claim 1 in the preparation of an antitumor agent.
In the above general formula (I), A represents "a monocyclic or bicyclic aromatic ring which may be substituted", which refers to an aromatic hydrocarbon ring or an aromatic heterocycle containing at least one of nitrogen, oxygen and sulfur atoms, each of which may have one to three substituents thereon. Such aromatic ring defined with respect to A include pyrrole, pyrazole, imidazole, thiophene, furan, thiazole, oxazole, benzene, pyridine, pyrimidine, pyrazine, pyridazine, naphthalene, quinoline, isoquinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, indole, isoindole, indolizine, indazole, benzofuran, benzothiophene, benzoxazole, benzimidazole, benzopyrazole and benzothiazole. They may have one to three substituents, and when two
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Masanobu Tani et al., Heterocycles, vol. 34, No. 12, pp. 2349-2363, 1992.
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Kito Kyosuke
Koyanagi Nozomu
Nagasu Takeshi
Okauchi Tatsuo
Owa Takashi
Cheng Wu C.
Eisai Co. Ltd.
Schofer Joseph L.
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