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EP0072710B1 Expired / Lapsed EP ⏱️ 0.0 years remaining

Carbapenem derivatives, their preparation and compositions containing them

Assignee: Sankyo Co Ltd
•
Filing: 1982-08-19
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Granted: 1986-02-19
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Expires: 2002-08-19
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Abstract

Abstract Compounds of the formula: <CHEM> wherein: R<1> represents a hydrogen atom, a C2-3 alkyl group, a 1-hydroxyethyl group or a 1-hydroxy-1-methylethyl group; R<2> represents a group of formula: <CHEM> in which, X represents a hydrogen atom, an alkyl group, a cyanoalkyl group, a haloalkyl group, an alkoxyalkyl group, an alkylthioalkyl group, an alkoxycarbonylalkyl group, an alkoxy group, an alkylthio group, an alkylsulphinyl group, an alkylsulphonyl group, a hydroxy group or a halogen atom, where each alkyl or alkoxy has 1-4 carbon atoms; Y represents a hydrogen atom, a C1-4 alkyl group, a C1-4 alkyl group substituted by a hydroxy, amino, carboxy or C1-4 alkoxy group, a C1-5 aliphatic acyl group, a C1-5 aliphatic acyl group substituted by a hydroxy, amino, carboxy or C1-4 alkoxy group, a group of formula -C(R<5>)=N-R<6> (R<5> and R<6> each represents a hydrogen or C1-4 alkyl). <CHEM> represents a 2- or 3-azetidinyl, a 2- or 3-pyrrolidinyl, a 2-, 3- or 4-piperidyl or a 3,4,5,6-tetrahydropyrimidin-5-yl. R<3> represents a carboxy group or a protected carboxy group, and pharmaceutically acceptable salts thereof, provided that when the group <CHEM> is a 4-piperidyl group then Y is not a C1-4 alkyl group and when <CHEM> is a 3-pyrrolidinyl group Y is not a group then Y is not a group -C(R<5>)=n-R<6>, are useful antibiotics.

Inventors

  • 👤 Tetsuo Chemical Research Laboratories Miyadera
  • 👤 Yukio Chemical Research Laboratories Sugimura
  • 👤 Toshihiko Chemical Research Lab. Hashimoto
  • 👤 Teruo Chemical Research Laboratories Tanaka
  • 👤 Kimio Chemical Research Laboratories Iino
  • 👤 Shinichi Research Institute Sugawara
  • 👤 Tomoyuki Chemical Research Laboratories Shibata

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-11-06 14:07
CPC Classifications
C; C07; C07D; C07D487/00; C07D487/02; C07D487/04; C07D477/00; C07D477/10; C07D477/12; C07D477/16; C07D477/20; C07D207/00; C07D207/02; C07D207/04; C07D207/10; C07D207/12; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55

Claims Analysis

Total Claims: 13
Claim 1
Independent Claim 52 words
A compound of formula: wherein R 1 represents a 1-hydroxyethyl group; R 3 represents a carboxy group or a protected carboxy group; and R 5 and R 6 are the same or different and each represents hydrogen or an alkyl group having 1 to 4 carbon atoms; and pharmaceutically acceptable salts thereof.
Claim 2
Dependent Claim 52 words
A compound of formula: wherein R 1 represents a 1-hydroxyethyl group; R 3 represents a carboxy group or a protected carboxy group; and R 5 and R 6 are the same or different and each represents hydrogen or an alkyl group having 1 to 4 carbon atoms; and pharmaceutically acceptable salts thereof.
Claim 3
Dependent Claim 27 words
A compound as claimed in Claim 1, wherein R 5 represents a methyl group and R B represents a hydrogen atom, or a pharmaceutically acceptable salt thereof.
Claim 4
Dependent Claim 22 words
A compound as claimed in Claim 1 or 2 wherein R 3 represents a carboxy group, or a pharmaceutically acceptable salt thereof.
Claim 5
Dependent Claim 22 words
A compound as claimed in any one of Claim 1 to 3, in the form of a salt with sodium or potassium.
Claim 6
Dependent Claim 34 words
A compound as claimed in any one of Claims 1 to 4, having the (5R, 6S) configuration and the 1-hydroxyethyl group for R 1 in the (R) configuration, or a pharmaceutically acceptable salt thereof.
Claim 7
Dependent Claim 8 words
2-(1-Acetimidoylpyrrolidin-3-ylthio)-6-(1-hydroxyethyl)-2-carbapenem-3-carboxylic acid, or a pharmaceutically acceptable salt thereof.
Claim 8
Dependent Claim 8 words
2-(1-Acetimidoylpyrrolidin-3-ylthio)-6-(1-hydroxyethyl)-2-carbapenem-3-carboxylic acid, or a pharmaceutically acceptable salt thereof.
Claim 9
Dependent Claim 8 words
2-(1-Formimidoylpyrrolidin-3-ylthio)-6-(1-hydroxyethyl)-2-carbapenem-3-carboxylic acid, or a pharmaceutically acceptable salt thereof.
Claim 10
Dependent Claim 8 words
2-(1-Formimidoylpyrrolidin-3-ylthio)-6-(1-hydroxyethyl)-2-carbapenem-3-carboxylic acid, or a pharmaceutically acceptable salt thereof.
Claim 11
Dependent Claim 157 words
A process for preparing a compound as claimed in any one of Claims 1 to 7, which process comprises the steps: reacting a compound of formula (II): (wherein R 7 represents the group defined for R 1 in which the hydroxy group is optionally protected, R S represents a protected carboxy group, and R 10 represents an alkylsulphonyl group, an arylsulphonyl group, a dialkyphosphoryl group or a diarylphosphoryl group) with a mercaptan of formula (III): (in which R 11 represents a 3-pyrrolidinyl group whose nitrogen atom is protected) to give a compound of formula (IV): (in which R 7 and R 8 and R 11 are as defined above) and removing a protecting group or groups from the compound of formula (IV) to give a compound of formula: in which Y represents a hydrogen atom, and converting the hydrogen atom represented by Y to a group ―C(R 5 )=N―R 6 , and, if necessary, salifying the compound.
Claim 12
Dependent Claim 129 words
A process for preparing a compound as claimed in any one of Claims 1 to 7, which process comprises the steps: reacting a compound of formula (II): (wherein R 7 represents the group defined for R 1 in which the hydroxy group is optionally protected, R 8 represents a protected carboxy group, and R 10 represents an alkysulphonyl group, an arylsulphonyl group, a dialkylphosphoryl group or a diarylphosphoryl group) with a compound of formula (V): (in which Y' represents a group of formula: in which R 5 is as defined above and R 6 ' represents one of the groups defined for R 6 or a protecting group for the nitrogen atom) and, if necessary, removing any protecting groups from the resulting compound, and, if necessary, salifying the compound.
Claim 13
Dependent Claim 41 words
A pharmaceutical composition comprising an effective amount of an antibacterial agent in admixture with a pharmaceutically acceptable carrier or diluent, wherein the antibacterial agent comprises at least one compound or salt as claimed in any one of Claims 1 to 7.

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