GB1391271A - Preparation of antibiotic compounds - Google Patents

Preparation of antibiotic compounds

Info

Publication number
GB1391271A
GB1391271A GB1244471A GB1244471A GB1391271A GB 1391271 A GB1391271 A GB 1391271A GB 1244471 A GB1244471 A GB 1244471A GB 1244471 A GB1244471 A GB 1244471A GB 1391271 A GB1391271 A GB 1391271A
Authority
GB
United Kingdom
Prior art keywords
forming
carried out
preparation
reaction
forming compound
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
GB1244471A
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.)
Glaxo Laboratories Ltd
Original Assignee
Glaxo Laboratories 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
Application filed by Glaxo Laboratories Ltd filed Critical Glaxo Laboratories Ltd
Priority to GB1244471A priority Critical patent/GB1391271A/en
Priority to BE782807A priority patent/BE782807A/en
Priority to CH635472A priority patent/CH576981A5/xx
Priority to DE19722221070 priority patent/DE2221070C2/en
Priority to NL7205789A priority patent/NL7205789A/xx
Priority to FR7215261A priority patent/FR2136786A5/fr
Priority to AT375572A priority patent/AT326815B/en
Priority to JP4323772A priority patent/JPS558987B1/ja
Publication of GB1391271A publication Critical patent/GB1391271A/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
    • C07D501/18—7-Aminocephalosporanic or substituted 7-aminocephalosporanic acids

Landscapes

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

Abstract

1391271 Preparation of 7-amino-cephalo- Sporins GLAXO LABORATORIES Ltd 24 April 1972 [30 April 1971] 12444/71 Heading C2C A process for the preparation of a 7-aminocephalosporanic acid comprises protecting both of the carboxyl groups of a 7-(4<SP>1</SP>-carboxybutanamido)cephalosporin - 4 - carboxylic acid by forming a double mixed anhydride thereof in an inert organic solvent under substantially anhydrous conditions, contacting the resultant solution with an imide halide-forming compound, commingling the resultant reaction mixture with an imino ether-forming compound, cleaving the reaction product and recovering the 7-aminocephalosporin formed. Suitable agents with which to form mixed anhydrides include acetyl, propionyl or chloroacetyl chloride, halides of benzoic acid or a nitro- or methoxy-benzoic acid. The mixed anhydrides may be formed in the temperature range -50‹ to +40‹ C., preferably -10‹ to +20‹ C. The mixed anhydride formation may be carried out in the presence of an organic tertiary base such as N,N-dimethylaniline or quinoline. The imide halide-forming compound may be phosphorus pentachloride and the imide halide-forming reaction may be carried out at -50‹ to + 50‹ C., preferably -30‹ to + 10‹ C. This reaction may be carried out in the presence of a tertiary base such as N,N-dimethylamine dr quinoline. The imino ether-forming compound may be a C 1 -C 6 alkanol such as methanol or a C 2 -C 4 alkane diol and the imino ether-forming reaction may be carried out in the temperature range -50‹ to + 20‹ C., preferably -50‹ to -10‹ C. The preparation of (6R, 7R)-3-acetoxymethyl- 7 - aminoceph - 3 - em - 4 - carboxylic acid from (6B, 7R) - 3 - acetoxymethyl - 7 - (4<SP>1</SP>- carboxybutanamido)ceph - 3 - em - 4 - carboxylic acid is described.
GB1244471A 1971-04-30 1971-04-30 Preparation of antibiotic compounds Expired GB1391271A (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
GB1244471A GB1391271A (en) 1971-04-30 1971-04-30 Preparation of antibiotic compounds
BE782807A BE782807A (en) 1971-04-30 1972-04-28 PROCESS FOR PREPARING ANTIBIOTIC COMPOUNDS
CH635472A CH576981A5 (en) 1971-04-30 1972-04-28
DE19722221070 DE2221070C2 (en) 1971-04-30 1972-04-28 Process for the preparation of 7-amino-cheph-3-em-4-carboxylic acid
NL7205789A NL7205789A (en) 1971-04-30 1972-04-28
FR7215261A FR2136786A5 (en) 1971-04-30 1972-04-28
AT375572A AT326815B (en) 1971-04-30 1972-04-28 PROCESS FOR THE PREPARATION OF A 7-AMINOCEPHALOSPORIN-4-CARBONONIC ACID
JP4323772A JPS558987B1 (en) 1971-04-30 1972-04-28

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1244471A GB1391271A (en) 1971-04-30 1971-04-30 Preparation of antibiotic compounds

Publications (1)

Publication Number Publication Date
GB1391271A true GB1391271A (en) 1975-04-16

Family

ID=10004718

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1244471A Expired GB1391271A (en) 1971-04-30 1971-04-30 Preparation of antibiotic compounds

Country Status (8)

Country Link
JP (1) JPS558987B1 (en)
AT (1) AT326815B (en)
BE (1) BE782807A (en)
CH (1) CH576981A5 (en)
DE (1) DE2221070C2 (en)
FR (1) FR2136786A5 (en)
GB (1) GB1391271A (en)
NL (1) NL7205789A (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GR70261B (en) * 1977-12-12 1982-09-02 Takeda Chemical Industries Ltd
JPH03100840U (en) * 1990-02-02 1991-10-22
US5391226A (en) * 1992-04-23 1995-02-21 Tiremix Corporation Rubber-crumb-reinforced cement concrete
JPH06324398A (en) * 1993-05-11 1994-11-25 Ryoichi Sato Board imprinting device
JPH0684451U (en) * 1993-05-11 1994-12-02 正宣 賀川 Camera with construction blackboard

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1241655A (en) * 1967-08-21 1971-08-04 Glaxo Lab Ltd Improvements in or relating to cephalosporin compounds

Also Published As

Publication number Publication date
JPS558987B1 (en) 1980-03-07
NL7205789A (en) 1972-11-01
DE2221070C2 (en) 1982-04-15
CH576981A5 (en) 1976-06-30
ATA375572A (en) 1975-03-15
AT326815B (en) 1975-12-29
BE782807A (en) 1972-10-30
FR2136786A5 (en) 1972-12-22
DE2221070A1 (en) 1972-11-23

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Legal Events

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