GB1101422A - 7-aminocephalosporanic acid derivatives - Google Patents

7-aminocephalosporanic acid derivatives

Info

Publication number
GB1101422A
GB1101422A GB2197763A GB2197763A GB1101422A GB 1101422 A GB1101422 A GB 1101422A GB 2197763 A GB2197763 A GB 2197763A GB 2197763 A GB2197763 A GB 2197763A GB 1101422 A GB1101422 A GB 1101422A
Authority
GB
United Kingdom
Prior art keywords
amino
carboxyceph
ylmethyl
formic acid
nitrosyl
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
GB2197763A
Inventor
Alan Gibson Long
Stephen Eardley
Vincent Arkley
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 GB2197763A priority Critical patent/GB1101422A/en
Priority to NL6411521A priority patent/NL6411521A/xx
Priority to DE19641445841 priority patent/DE1445841A1/en
Priority to FR990119A priority patent/FR1451983A/en
Priority to CH1288364A priority patent/CH461491A/en
Publication of GB1101422A publication Critical patent/GB1101422A/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
    • 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

Abstract

Derivatives of 7-aminocephalosporanic acid of formula <FORM:1101422/C2/1> where X is an azide group or the residue of a sulphur-containing nucleophile linked through sulphur, and salts thereof, are produced by reacting a compound of formula <FORM:1101422/C2/2> wherein X has the aforesaid meaning, or a salt thereof, with a nitrosyl halide in a liquid solvent medium comprising formic acid, and decomposing the resultant intermediate with water or a C1-C3 alkanol. Nitrosyl chloride or nitrosyl bromide are preferred and may be formed in situ from a hydrogen halide and alkyl nitrite. The solvent may be substantially anhydrous formic acid or may be formic acid and an inert solvent, e.g. a nitrohydrocarbon. Typical compounds are S-(7-amino-4-carboxyceph-3-em-3-ylmethyl) isothiourea; S-(7-amino-4-carboxyceph - 3 - em - 3 - ylmethyl) thiobenzoate; S-(7 - amino - 4 - carboxyceph - 3 - em - 3 - yl-methyl) thiopicolinate; S-(71-amino-41-carboxy-ceph -31 - em - 31 - ylmethyl) thio - 4 - methyl-pyrimidine S - (71 - amino - 41 - carboxyceph-31 - em - 31 - ylmethyl) thio - 4,6 - dimethyl-pyrimidine and 7-amino-3-azidomethylceph-3-em -4-carboxylic acid.
GB2197763A 1963-10-04 1963-10-04 7-aminocephalosporanic acid derivatives Expired GB1101422A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
GB2197763A GB1101422A (en) 1963-10-04 1963-10-04 7-aminocephalosporanic acid derivatives
NL6411521A NL6411521A (en) 1963-10-04 1964-10-02
DE19641445841 DE1445841A1 (en) 1963-10-04 1964-10-02 Process for the preparation of 7-aminocephalosporanic acid derivatives
FR990119A FR1451983A (en) 1963-10-04 1964-10-02 Process for the preparation of 7-aminocephalosporanic acid derivatives
CH1288364A CH461491A (en) 1963-10-04 1964-10-05 Process for the preparation of 7-aminocephalosporanic acid derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2197763A GB1101422A (en) 1963-10-04 1963-10-04 7-aminocephalosporanic acid derivatives

Publications (1)

Publication Number Publication Date
GB1101422A true GB1101422A (en) 1968-01-31

Family

ID=10171931

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2197763A Expired GB1101422A (en) 1963-10-04 1963-10-04 7-aminocephalosporanic acid derivatives

Country Status (4)

Country Link
CH (1) CH461491A (en)
DE (1) DE1445841A1 (en)
GB (1) GB1101422A (en)
NL (1) NL6411521A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6642020B2 (en) 2001-04-19 2003-11-04 Bioferma Murcia S.A. Process for preparing cephalosporin derivatives

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6642020B2 (en) 2001-04-19 2003-11-04 Bioferma Murcia S.A. Process for preparing cephalosporin derivatives

Also Published As

Publication number Publication date
CH461491A (en) 1968-08-31
DE1445841A1 (en) 1969-01-23
NL6411521A (en) 1965-04-05

Similar Documents

Publication Publication Date Title
SE7502286L (en)
GB1101422A (en) 7-aminocephalosporanic acid derivatives
ES470757A1 (en) 2-Lower alkyl-7-substituted-2 or 3-cephem-4-carboxylic acid compounds
GB1119696A (en) Process for the preparation of thiuram monosulphides
GB1100714A (en) 3-deoxy-ribofuranosyl derivatives
GB1071231A (en) Nucleosides
ES419749A1 (en) Process for making phosphonothioureides
GB777544A (en) Water soluble organic copper compounds and a process for their production
GB1040162A (en) Process for the production of 1-cycloalkylmethyl-substituted 1,4-benzodiazepines
US2860165A (en) Diaryl disulfonamides and processes for their production
GB961678A (en) Process for the manufacture of thiuram disulphides
GB844946A (en) New 2-(n-substituted)-acylamino-1,3,4-thiadiazole-5-sulfonamides
GB1005049A (en) Sulphur containing herbicides
GB1033260A (en) Stabilization of aqueous n,n-dialkylhydroxylamine solutions
GB1124250A (en) Hydrazinium salts and their use as plant growth inhibitors
GB1058535A (en) 7-(-a,-ß-unsaturated acylamino)cephalosporanic acid and derivatives thereof
GB1059003A (en) Substituted saccharins
IE42384L (en) Oxothiodimethylamides
JPS5699274A (en) Antistatic agent
GB1086038A (en) Unsaturated sulphonic acids
GB1416434A (en) Manufacture of pyrimidines
ES302770A1 (en) Procedure for the production of heterocyclic compounds (Machine-translation by Google Translate, not legally binding)
GB1049769A (en) Organic compounds containing an isocyclic and a heterocyclic non-aromatic ring and aprocess for the production of these compounds
ES286459A1 (en) Procedure for the obtaining of new antitusive compounds (Machine-translation by Google Translate, not legally binding)
GB675611A (en) Improvements in or relating to substituted piperazines