GB1041985A - Process for the manufacture of 7-amino-cephalosporanic acids - Google Patents

Process for the manufacture of 7-amino-cephalosporanic acids

Info

Publication number
GB1041985A
GB1041985A GB679964A GB679964A GB1041985A GB 1041985 A GB1041985 A GB 1041985A GB 679964 A GB679964 A GB 679964A GB 679964 A GB679964 A GB 679964A GB 1041985 A GB1041985 A GB 1041985A
Authority
GB
United Kingdom
Prior art keywords
group
acid
amino
halide
iminoether
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
GB679964A
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.)
BASF Schweiz AG
Original Assignee
Ciba AG
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 CH199263A external-priority patent/CH433316A/en
Priority claimed from CH267563A external-priority patent/CH504471A/en
Application filed by Ciba AG filed Critical Ciba AG
Publication of GB1041985A publication Critical patent/GB1041985A/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

7-Amino-cephalosporanic acid or a derivative thereof with a free amino group of Formula I <FORM:1041985/C2/1> or an ester thereof, in which R represents an esterified OH group or in which R and the -OH group of the 4-carboxylic group are replaced by a lactone oxygen atom -O-, is prepared by treating cephalosporin C or a derivative thereof of Formula II <FORM:1041985/C2/2> whose amino and carboxylic groups are blocked and in which R has the meaning given above or in which R and the -OH group of the 4-carboxylic group are replaced by a lactone oxygen atom -O-, with an agent forming an imide halide, the imide halide is converted into the corresponding iminoether and the latter is hydrolysed with water in the presence of an acidic or basic substance at a pH value of at most 10 and, if desired, the group blocking the 4-carboxyl group is split off by hydrogenolysis or acid hydrolysis. The agent forming an imide halide is an acid halide derived from P, S or C or an oxygen acid thereof, e.g. phosphorus oxychloride. The imide halide is reacted with an alcohol in the presence of a tertiary amine, e.g. pyridine to form the iminoether. The hydrolysis of the iminoether to form a 7-aminocephalosporanic ester may be carried out by means of a mineral or organic acid, e.g. trifluoracetic acid or p-toluene sulphonic acid.
GB679964A 1963-02-18 1964-02-18 Process for the manufacture of 7-amino-cephalosporanic acids Expired GB1041985A (en)

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
CH199263A CH433316A (en) 1963-02-18 1963-02-18 New process for the production of 7-aminocephalosporan compounds
CH267563A CH504471A (en) 1963-11-25 1963-03-01 7-Amino-cephalosporanic acid derivs
CH424963 1963-04-03
CH735863 1963-06-13
CH824663 1963-07-02
CH1211263 1963-10-02
CH1360063 1963-11-06
CH73064 1964-01-22

Publications (1)

Publication Number Publication Date
GB1041985A true GB1041985A (en) 1966-09-07

Family

ID=27570319

Family Applications (1)

Application Number Title Priority Date Filing Date
GB679964A Expired GB1041985A (en) 1963-02-18 1964-02-18 Process for the manufacture of 7-amino-cephalosporanic acids

Country Status (7)

Country Link
BE (1) BE643899A (en)
BR (1) BR6456924D0 (en)
DK (1) DK118506B (en)
GB (1) GB1041985A (en)
IT (1) IT1060055B (en)
NL (1) NL142165B (en)
SE (1) SE347003B (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2436771A1 (en) * 1973-08-01 1975-02-20 Glaxo Lab Ltd CEPHALOSPORINE COMPOUNDS
EP0014567A1 (en) * 1979-02-01 1980-08-20 Eli Lilly And Company Processes for preparation of beta-lactam compounds
US4562253A (en) * 1982-08-06 1985-12-31 Biochemie Gesellschaft M.B.H. Deacylation of amides

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH517119A (en) * 1967-09-01 1971-12-31 Ciba Geigy Ag New process for the production of 7-aminocephalosporanic acid

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2436771A1 (en) * 1973-08-01 1975-02-20 Glaxo Lab Ltd CEPHALOSPORINE COMPOUNDS
EP0014567A1 (en) * 1979-02-01 1980-08-20 Eli Lilly And Company Processes for preparation of beta-lactam compounds
US4562253A (en) * 1982-08-06 1985-12-31 Biochemie Gesellschaft M.B.H. Deacylation of amides

Also Published As

Publication number Publication date
NL6401421A (en) 1964-08-19
DK118506B (en) 1970-08-31
BR6456924D0 (en) 1973-08-28
NL142165B (en) 1974-05-15
BE643899A (en) 1964-08-17
IT1060055B (en) 1982-07-10
SE347003B (en) 1972-07-24

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