GB1438872A - 7-beta-aminoacylamino-3-substituted-3-cephem-4-carboxylic acid derivatives and preparation thereof - Google Patents

7-beta-aminoacylamino-3-substituted-3-cephem-4-carboxylic acid derivatives and preparation thereof

Info

Publication number
GB1438872A
GB1438872A GB4121873A GB4121873A GB1438872A GB 1438872 A GB1438872 A GB 1438872A GB 4121873 A GB4121873 A GB 4121873A GB 4121873 A GB4121873 A GB 4121873A GB 1438872 A GB1438872 A GB 1438872A
Authority
GB
United Kingdom
Prior art keywords
hydrogen
derivatives
amino
prepared
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB4121873A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Fujisawa Pharmaceutical Co Ltd
Original Assignee
Fujisawa Pharmaceutical Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from JP11598372A external-priority patent/JPS5725557B2/ja
Priority claimed from JP1863673A external-priority patent/JPS563878B2/ja
Application filed by Fujisawa Pharmaceutical Co Ltd filed Critical Fujisawa Pharmaceutical Co Ltd
Publication of GB1438872A publication Critical patent/GB1438872A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D501/14—Compounds having a nitrogen atom directly attached in position 7
    • C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
    • C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
    • C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
    • C07D501/36—Methylene radicals, substituted by sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D501/14—Compounds having a nitrogen atom directly attached in position 7
    • C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
    • C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D501/14—Compounds having a nitrogen atom directly attached in position 7
    • C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
    • C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
    • C07D501/22—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with radicals containing only hydrogen and carbon atoms, attached in position 3
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Cephalosporin Compounds (AREA)

Abstract

1438872 7 - [# - Aminoacylamino] - 3 - substituted - 3 - cephem-4 - carboxylic acid derivatives FUJISAWA PHARMACEUTICAL CO Ltd 31 Aug 1973 [17 Nov 1972 14 Feb 1973] 41218/73 Heading C2C Novel cephalosporamic acid derivatives have the formula wherein R 1 is hydrogen lower alkyl, lower alkenyl, aryl or a heterocyclic group, R 2 is hydrogen or lower alkyl or R 1 and R 2 mean, taken together with the adjacent carbon atom, cycloalkyl or cycloalkenyl, R 3 is hydrogen, lower alkylthio or a heterocyclic thio group but excluding 5-methyl-1,3,4-thio diazol-2-ylthio when R 1 and R 2 taken together with the adjacent carbon atom are cyclohexyl and M is hydrogen, and M is hydrogen or a non-toxic, pharmaceutically acceptable cation. These derivatives may be prepared by acylating 7- amino - 3 - substituted - 3 - cephem - 4 - carboxylic acids of the formula with a #-amino aliphatic carboxylic acid derivative of the formula wherein X is protected amino, and if necessary removing the protective group of the amino radical. In the instance wherein R 3 is lower alkylthio or a heterocyclic-thio group, the derivatives may be prepared by reacting 7-acylated aminocephalosporacic acids with nucleophiles of formula R 3 -H and then if necessary, removing the protective groups of the amino radical. Further, when R 3 is hydrogen, the derivatives may be prepared by reducing 7-acylated amino cephalosporanic acids, and then, if necessary, removing a protective group on the amino radical. 1 - Aminocyclohexane - 1 - acetyl chloride is prepared by reacting the free acid with thionylchloride. The derivatives may be used in the form of a pharmaceutical preparation for therapeutic administration.
GB4121873A 1972-11-17 1973-08-31 7-beta-aminoacylamino-3-substituted-3-cephem-4-carboxylic acid derivatives and preparation thereof Expired GB1438872A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP11598372A JPS5725557B2 (en) 1972-11-17 1972-11-17
JP1863673A JPS563878B2 (en) 1973-02-14 1973-02-14

Publications (1)

Publication Number Publication Date
GB1438872A true GB1438872A (en) 1976-06-09

Family

ID=26355341

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4121873A Expired GB1438872A (en) 1972-11-17 1973-08-31 7-beta-aminoacylamino-3-substituted-3-cephem-4-carboxylic acid derivatives and preparation thereof

Country Status (7)

Country Link
CA (1) CA1032534A (en)
CH (1) CH589658A5 (en)
DE (1) DE2344451C2 (en)
FR (1) FR2206934B1 (en)
GB (1) GB1438872A (en)
NL (1) NL7312366A (en)
SE (1) SE415019B (en)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3518260A (en) * 1965-03-08 1970-06-30 Lilly Co Eli Method for preparing aminoacyl cephalosporins
US3641021A (en) * 1969-04-18 1972-02-08 Lilly Co Eli 3 7-(ring-substituted) cephalosporin compounds

Also Published As

Publication number Publication date
DE2344451C2 (en) 1983-02-03
SE415019B (en) 1980-09-01
NL7312366A (en) 1974-05-21
CA1032534A (en) 1978-06-06
FR2206934A1 (en) 1974-06-14
FR2206934B1 (en) 1977-01-28
DE2344451A1 (en) 1974-05-30
CH589658A5 (en) 1977-07-15

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee