GB1455017A - Epimerization of cephem-related compounds - Google Patents

Epimerization of cephem-related compounds

Info

Publication number
GB1455017A
GB1455017A GB5130373A GB5130373A GB1455017A GB 1455017 A GB1455017 A GB 1455017A GB 5130373 A GB5130373 A GB 5130373A GB 5130373 A GB5130373 A GB 5130373A GB 1455017 A GB1455017 A GB 1455017A
Authority
GB
United Kingdom
Prior art keywords
formula
cephem
alkoxy
compound
epimerisation
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
GB5130373A
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.)
Merck and Co Inc
Original Assignee
Merck and Co Inc
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
Application filed by Merck and Co Inc filed Critical Merck and Co Inc
Publication of GB1455017A publication Critical patent/GB1455017A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/44—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reduction and hydrolysis of nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
    • C07D205/085—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a nitrogen atom directly attached in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
    • C07D205/09—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4
    • C07D205/095—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4 and with a nitrogen atom directly attached in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
    • C07D265/06—1,3-Oxazines; Hydrogenated 1,3-oxazines not condensed with other rings
    • C07D265/08—1,3-Oxazines; Hydrogenated 1,3-oxazines not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D463/00—Heterocyclic compounds containing 1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D463/02—Preparation
    • C07D463/06—Preparation from compounds already containing the ring or condensed ring systems, e.g. by dehydrogenation of the ring, by introduction, elimination or modification of substituents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D505/00—Heterocyclic compounds containing 5-oxa-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/568—Four-membered rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Cephalosporin Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

1455017 Epimerisation of 7-α-aminocephem derivatives MERCK & CO Inc 5 Nov 1973 [6 Nov 1972] 51303/73 Heading C2C A process for epimerisation of 7α-cephem compounds of Formula Ib wherein R 1 is a blocking group, R<SP>1</SP> is H, halogen, C 1-6 alkanoyloxy, carbamoyloxy optionally N-substituted, C 1-5 alkoxy, benzyloxy, (C 1-5 )- alkoxy(C 1-5 )alkoxy or substituted benzyloxy and X is -O-, -CH 2 -, -NH- or -NY- where Y is C 1-6 alkyl comprises reacting the said compound with an aldehyde or ketone capable of forming a stable imine derivative of Formula IV which is epimerized by reaction with a strong base in the presence of an aprotic solvent and a dipolar aprotic co-solvent followed by addition of a molar excess of acid or water to give a compound of Formula V which is reacted with an acid optionally in the presence of an amine to give the 7-#-cephem compound of Formula Ia The 7-α-cephem starting compounds are prepared as in Specification 1,455,016.
GB5130373A 1972-11-06 1973-11-05 Epimerization of cephem-related compounds Expired GB1455017A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US30390672A 1972-11-06 1972-11-06

Publications (1)

Publication Number Publication Date
GB1455017A true GB1455017A (en) 1976-11-10

Family

ID=23174217

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5130373A Expired GB1455017A (en) 1972-11-06 1973-11-05 Epimerization of cephem-related compounds

Country Status (6)

Country Link
JP (1) JPS4976895A (en)
CH (1) CH587262A5 (en)
DE (1) DE2355210A1 (en)
FR (1) FR2205518B1 (en)
GB (1) GB1455017A (en)
NL (1) NL7314706A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4529722A (en) * 1982-12-06 1985-07-16 Shionogi & Co., Ltd. Oxacephalosporin derivatives

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4226866A (en) 1972-11-06 1980-10-07 Merck & Co., Inc. Novel antibiotic analogues of cephalosporins
US4108992A (en) 1975-05-10 1978-08-22 Beecham Group Limited Cephalosporin analogues and compositions
CA1085392A (en) 1976-03-25 1980-09-09 Masayuki Narisada Arylmalonamido-1-oxadethiacephalosporins
JPS607635B2 (en) * 1976-04-27 1985-02-26 塩野義製薬株式会社 Oxazolidine compounds
US4089956A (en) * 1976-09-08 1978-05-16 Smithkline Corporation 7-Acylamino-8-oxo-3-oxa-1-azabicyclo[4.2.0]octane-2-carboxylic acid derivatives and bactericidal compositions and use thereof
IT1102408B (en) * 1977-12-23 1985-10-07 Fujisawa Pharmaceutical Co ANALOGUE COMPOUNDS OF CEPHALOSPHORINE AND PROCEDURES FOR THEIR PREPARATION

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4529722A (en) * 1982-12-06 1985-07-16 Shionogi & Co., Ltd. Oxacephalosporin derivatives

Also Published As

Publication number Publication date
NL7314706A (en) 1974-05-08
FR2205518A1 (en) 1974-05-31
JPS4976895A (en) 1974-07-24
FR2205518B1 (en) 1977-05-27
DE2355210A1 (en) 1974-05-16
CH587262A5 (en) 1977-04-29

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Legal Events

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