Organic compounds -- part of the class 532-570 series – Organic compounds – Unsubstituted hydrocarbyl chain between the ring and the -c-...
Patent
1994-09-21
1997-03-04
Cook, Rebecca
Organic compounds -- part of the class 532-570 series
Organic compounds
Unsubstituted hydrocarbyl chain between the ring and the -c-...
514210, C07D48704
Patent
active
056080565
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
This application is a 370 of PCT/JP93/00469 filed Apr. 9, 1993.
The present invention relates to novel azabicyclo compounds and pharmaceutically acceptable salts thereof.
More particularly, it relates to novel 3-pyrrolidinylthio-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid compounds and pharmaceutically acceptable salts thereof, which have antimicrobial activity, to processes for the preparation thereof, to a pharmaceutical composition comprising the same, and to a use of the same as a medicament and in the treatment of infectious diseases in a human being or animal.
INDUSTRIAL APPLICABILITY
Accordingly, one object of the present invention is to provide novel 3-pyrrolidinylthio-1-azabicyclo-[3.2.0]hept-2-ene-2-carboxylic acid compounds and pharmaceutically acceptable salts thereof, which are highly active against a number of pathogenic microorganisms and are useful as antimicrobial agents.
Another object of the present invention is to provide processes for the preparation of novel 3-pyrrolidinylthio-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid compounds and salts thereof.
A further object of the present invention is to provide a pharmaceutical composition comprising, as an active ingredient, said 3-pyrrolidinylthio-1-azabicyclo-[3.2.0]hept-2-ene-2-carboxylic acid compounds and pharmaceutically acceptable salts thereof.
Still further object of the present invention is to provide a use of said 3-pyrrolidinylthio-1-azabicyclo-[3.2.0]hept-2-ene-2-carboxylic acid compounds and pharmaceutically acceptable salts thereof as a medicament and in the treatment of infectious diseases by pathogenic microorganisms in a human being or animal.
DISCLOSURE OF INVENTION
The object 3-pyrrolidinylthio-1-azabicyclo[3.2.0]-hept-2-ene-2-carboxylic acid compounds are novel and can be represented by the following general formula: ##STR2## in which R.sup.1 is carboxy or protected carboxy, acceptable salts thereof.
Suitable pharmaceutically acceptable salts of the object compound (I) are conventional non-toxic salts and may include a salt with a base such as an inorganic base salt, for example, an alkali metal salt (e.g. sodium salt, potassium salt, etc.), an alkaline earth metal salt (e.g. calcium salt, magnesium salt, etc.), an ammonium salt, an organic base salt, for example, an organic amine salt (e.g. triethylamine salt, pyridine salt, picoline salt, ethanolamine salt, triethanolamine salt, dicyclohexylamine salt, N,N'-dibenzylethylenediamine salt, etc.); a salt with an acid such as inorganic acid addition salt (e.g. hydrochloride, hydrobromide, sulfate, fluorosulfate, phosphate, etc.), an organic acid addition salt (e.g. formate, acetate, trifluoroacetate, maleate, tartrate, methanesulfonate, benzenesulfonate, trifluoromethanesulfonate etc.); a salt with a basic or acidic amino acid (e.g. arginine, aspartic acid, glutamic acid, etc.); an intermolecular or intramolecular quaternary salt; and the like.
The said intermolecular quaternary salt can be formed, for example, between the tertiary nitrogen atom of the pyridyl, 2-oxopiperazin-1-yl, dihydropyrimidinyl, pyrazolyl, triazolyl, pyrimidinyl, 2,3-dihydroimidazo-[1,2-b]pyrazol-1-yl, or the imidazolyl group in R.sup.4 and lower alkyl (e.g. methyl, etc.), carbamoyl(lower)alkyl (e.g. carbamoylmethyl, etc.), N,N-di(lower)alkylcarbamoyl(lower)alkyl (e.g. dimethylcarbamoylmethyl, etc.), N-[hydroxy(lower)alkyl]carbamoyl(lower)alkyl [e.g. N-(2-hydroxyethyl)carbamoylmethyl, etc.], amino(lower)alkyl (e.g. 3-aminopropyl, etc.) or protected amino(lower)alkyl [e.g. 3-(allyloxycarbonylamino)propyl, etc.], and such a suitable intermolecular quaternary salt may include 3-(lower)alkyl-1-(or 2- or 5-)imidazolio (or trifluoromethanesulfonate), 3-carbamoyl(lower)alkyl-1-(or 2- or 5-)imidazolio (or trifluoromethanesulfonate), 3-amino(or protected amino)(lower)alkyl-1-imidazolio halide, 1-(lower)alkylpyridinio halide, 1-carbamoyl(lower)alkylpyridinio halide, 1-[N,N-di(lower)alkylcarbamoyl(lower)alkyl]pyridinio halide, 1-[N-{hydroxy(lower)alkyl}carbamoyl(lower)alkyl]pyridin
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Hattori Kohji
Matsuda Keiji
Murata Masayoshi
Nakajima Takashi
Tsutsumi Hideo
Cook Rebecca
Fujisawa Pharmaceutical Co. Ltd.
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