GB1073530A - Process for the preparation of cephalosporins - Google Patents

Process for the preparation of cephalosporins

Info

Publication number
GB1073530A
GB1073530A GB4967663A GB4967663A GB1073530A GB 1073530 A GB1073530 A GB 1073530A GB 4967663 A GB4967663 A GB 4967663A GB 4967663 A GB4967663 A GB 4967663A GB 1073530 A GB1073530 A GB 1073530A
Authority
GB
United Kingdom
Prior art keywords
alkyl
group
formula
groups
product
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
GB4967663A
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.)
AstraZeneca AB
Original Assignee
Astra AB
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 Astra AB filed Critical Astra AB
Publication of GB1073530A publication Critical patent/GB1073530A/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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
    • A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/545—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, cefaclor, or cephalexine
    • 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
    • C07D501/02—Preparation
    • C07D501/04—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
    • C07D501/06—Acylation of 7-aminocephalosporanic acid
    • 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
    • C07D501/26—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group
    • C07D501/32—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group with the 7-amino radical acylated by an araliphatic carboxylic acid, which is substituted on the aliphatic radical by hetero atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Cephalosporin Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)

Abstract

The invention relates to 7-(a -azidophenyl-acetamido) cephalosporanic acid and non-toxic salts thereof. Cephalosporin compounds of formula <FORM:1073530/C2/1> and their non-toxic salts, wherein R represents an organic group, are prepared by reacting 7-aminocephalosporanic acid with a silylating agent of formula <FORM:1073530/C2/2> wherein R1, R2 and R3 are alkyl groups of 1 to 6 C atoms, X is a halogen atom or a group -NR4R5 (wherein R4 is H or C1- 6 alkyl and R5 is H or C1- 6 alkyl or a group <FORM:1073530/C2/3> reacting the silylated product of the silylation with a carboxylic acid of formula R.COOH or a reactive derivative thereof, removing by hydrolysis any silyl groups and optionally converting the resulting product into a non-toxic salt. A chlorotrialkylsilane may be used in an organic solvent in the presence of a basic tertiary amine. Alternatively, excess of a N-trialkylsilyl-dialkylamine may be used at a temperature of 30 DEG to 170 DEG C. with simultaneous removal of the dialkylamine by-product. R may be alkyl, cycloalkyl, aryl, aryloxyalkyl, *?* or heterocyclic which may be substituted by one or more halogen atoms, alkyl, aryloxy, alkoxy, hydroxy, acyloxy, carboxy, carbalkoxy, alkyl mercapto, mercapto, sulphoxy, sulphonyl, nitro or amino, aminoxy oximino or alkoxyimino groups. The amino group may be protected. Salts are formed with metals e.g. calcium and aluminium and amines e.g. procaine.
GB4967663A 1962-12-14 1963-12-16 Process for the preparation of cephalosporins Expired GB1073530A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
SE1352462A SE311519B (en) 1962-12-14 1962-12-14

Publications (1)

Publication Number Publication Date
GB1073530A true GB1073530A (en) 1967-06-28

Family

ID=20297538

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4967663A Expired GB1073530A (en) 1962-12-14 1963-12-16 Process for the preparation of cephalosporins

Country Status (6)

Country Link
DE (1) DE1445434A1 (en)
DK (1) DK121231B (en)
FI (1) FI42332C (en)
GB (1) GB1073530A (en)
NO (1) NO132692C (en)
SE (1) SE311519B (en)

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2016284A1 (en) * 1968-08-23 1970-05-08 Lilly Co Eli
FR2081379A1 (en) * 1969-12-18 1971-12-03 Koninkl Nederland Ch
FR2123545A1 (en) * 1971-01-29 1972-09-08 Glaxo Lab Ltd (2-hydroxy (or alkoxy)imino)acylamido penicillanic and - cephalosporanic acids - useful as antibiotics and intermediates
FR2123544A1 (en) * 1971-01-29 1972-09-08 Glaxo Lab Ltd
US3694437A (en) * 1970-08-19 1972-09-26 Lilly Co Eli Process for preparing cephalosporin compounds
FR2137900A1 (en) * 1971-05-14 1972-12-29 Glaxo Lab Ltd
FR2181649A1 (en) * 1972-01-03 1973-12-07 Hoffmann La Roche
FR2287231A1 (en) * 1971-05-14 1976-05-07 Glaxo Lab Ltd (OXIMINO ETHERIFIED) CARBOXYLIC ACIDS AND THEIR DERIVATIVES
US4007174A (en) * 1973-07-06 1977-02-08 Glaxo Laboratories Limited Cephalosporin compounds
US4024134A (en) * 1971-01-29 1977-05-17 Glaxo Laboratories Limited Syn isomers of cephalosporins having α-hydroximino- or α-acyloxyiminoacylamido groups at position-7
US4209616A (en) * 1971-01-29 1980-06-24 Glaxo Laboratories Limited Syn isomers of cephalosporins having α-hydroximino- or α-acyloxyiminoacylamido groups at position-7
US4223135A (en) 1979-03-19 1980-09-16 Bristol-Myers Company Production of cephalosporins
US4316017A (en) 1979-03-19 1982-02-16 Bristol-Myers Company Cephalosporin intermediates
US4316016A (en) 1979-03-19 1982-02-16 Bristol-Myers Company Cephalosporin intermediates
DK151024B (en) * 1977-09-06 1987-10-12 Gist Brocades Nv METHOD FOR PREPARING 6- (D-ALFA-AMINO- (P-HYDROXYPHENYL) ACETIMIDO) -PENICILLANIC ACID
US5831086A (en) * 1994-12-23 1998-11-03 Biochemie Gesellschaft M.B.H. Production of cefotaxime and new sodium salts
US5998610A (en) * 1994-11-21 1999-12-07 Biochemie Gesellschaft M.B.H. Silylation process

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2016284A1 (en) * 1968-08-23 1970-05-08 Lilly Co Eli
FR2081379A1 (en) * 1969-12-18 1971-12-03 Koninkl Nederland Ch
US3694437A (en) * 1970-08-19 1972-09-26 Lilly Co Eli Process for preparing cephalosporin compounds
FR2123545A1 (en) * 1971-01-29 1972-09-08 Glaxo Lab Ltd (2-hydroxy (or alkoxy)imino)acylamido penicillanic and - cephalosporanic acids - useful as antibiotics and intermediates
FR2123544A1 (en) * 1971-01-29 1972-09-08 Glaxo Lab Ltd
US4209616A (en) * 1971-01-29 1980-06-24 Glaxo Laboratories Limited Syn isomers of cephalosporins having α-hydroximino- or α-acyloxyiminoacylamido groups at position-7
US4024134A (en) * 1971-01-29 1977-05-17 Glaxo Laboratories Limited Syn isomers of cephalosporins having α-hydroximino- or α-acyloxyiminoacylamido groups at position-7
FR2287231A1 (en) * 1971-05-14 1976-05-07 Glaxo Lab Ltd (OXIMINO ETHERIFIED) CARBOXYLIC ACIDS AND THEIR DERIVATIVES
FR2137899A1 (en) * 1971-05-14 1972-12-29 Glaxo Lab Ltd
FR2137900A1 (en) * 1971-05-14 1972-12-29 Glaxo Lab Ltd
FR2181649A1 (en) * 1972-01-03 1973-12-07 Hoffmann La Roche
US4007174A (en) * 1973-07-06 1977-02-08 Glaxo Laboratories Limited Cephalosporin compounds
DK151024B (en) * 1977-09-06 1987-10-12 Gist Brocades Nv METHOD FOR PREPARING 6- (D-ALFA-AMINO- (P-HYDROXYPHENYL) ACETIMIDO) -PENICILLANIC ACID
US4223135A (en) 1979-03-19 1980-09-16 Bristol-Myers Company Production of cephalosporins
US4316017A (en) 1979-03-19 1982-02-16 Bristol-Myers Company Cephalosporin intermediates
US4316016A (en) 1979-03-19 1982-02-16 Bristol-Myers Company Cephalosporin intermediates
US5998610A (en) * 1994-11-21 1999-12-07 Biochemie Gesellschaft M.B.H. Silylation process
US5831086A (en) * 1994-12-23 1998-11-03 Biochemie Gesellschaft M.B.H. Production of cefotaxime and new sodium salts

Also Published As

Publication number Publication date
FI42332B (en) 1970-03-31
NO132692C (en) 1975-12-17
DK121231B (en) 1971-09-27
NO132692B (en) 1975-09-08
DE1445434A1 (en) 1969-01-16
SE311519B (en) 1969-06-16
FI42332C (en) 1970-07-10

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