GB1082962A - Derivatives of 7-aminocephalosporanic acid - Google Patents

Derivatives of 7-aminocephalosporanic acid

Info

Publication number
GB1082962A
GB1082962A GB2128463A GB2128463A GB1082962A GB 1082962 A GB1082962 A GB 1082962A GB 2128463 A GB2128463 A GB 2128463A GB 2128463 A GB2128463 A GB 2128463A GB 1082962 A GB1082962 A GB 1082962A
Authority
GB
United Kingdom
Prior art keywords
formula
compound
carboxylate
hydrogen
compounds
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
GB2128463A
Inventor
Stephen Eardley
Gabrielle Griffin
Wilfred Frank Wall
Michael Fatherley
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 GB2128463A priority Critical patent/GB1082962A/en
Priority to NL646403229A priority patent/NL140243B/en
Priority to ES298060A priority patent/ES298060A1/en
Priority to DE19641445831 priority patent/DE1445831C3/en
Priority to FR968973A priority patent/FR1524027A/en
Priority to FR968974A priority patent/FR4201M/fr
Priority to BE645868D priority patent/BE645868A/xx
Priority to AT271664A priority patent/AT261110B/en
Priority to CH405664A priority patent/CH515274A/en
Publication of GB1082962A publication Critical patent/GB1082962A/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
    • 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
    • C07D501/38—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof
    • 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
    • C07D501/14—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
    • C07D501/38—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof
    • C07D501/42—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof with the 7-amino radical acylated by an araliphatic carboxylic acid

Abstract

The invention relates to 7-aminocephalosporanic acid derivatives of Formula II <FORM:1082962/C2/1> wherein R1 is aralkyl; R2 is carbamoyl, caroxyl or alkoxycarbonyl; and x is 1 or 2. R1 may be a substituted benzyl of formulae <FORM:1082962/C2/2> wherein R3 is acyl or hydrogen, X is O or imino, R4 is alkoxy, alkylthio, acyl, carboxyalkyl, alkoxycarbonyloxy, nitro, alkyl or halogen; R5 is as R4 or hydrogen. The alkyl, alkanoyl and alkoxy contain 1-6 C atoms. Typical compounds are N-(7-phenylacetamidoceph-3-em-3-ylmethyl) - 31 - carbamoylpyridinium - 4 - carboxylate, N - (7 - phenyl - acetamidoceph - 3 - em - 3 - ylmethyl) - 31 - carboxypyridinium - 4 - carboxylate and N - (7 - phenylacetamidoceph - 3 - em - 3 - ylmethyl) - 41 - methoxycarbonyl-pyridinium-4-carboxylate. The compounds are prepared by reacting a compound of formula <FORM:1082962/C2/3> where R6 is H or R1CO and R1 has the above meaning, or a water-soluble salt thereof, with a compound of formula <FORM:1082962/C2/4> where R2 and X have the above meanings, in a strongly polar medium, the resulting compound where R6 is hydrogen being phenylacetylated by reaction with the appropriate phenylacetylating agent. Water, aqueous acetone or aqueous N,N-dimethylformamide at pH 5 to 8 are the preferred media for the preparation of the compounds of the invention. Alternatively, 7-aminocephalosporanic acid may be phenylacetylated to form Compound III <FORM:1082962/C2/5> or reacted with the nucleophile of Formula IV to form Compound V <FORM:1082962/C2/6> Compounds of Formula V may be prepared from a compound of Formula VI <FORM:1082962/C2/7> by methods known for the conversion of cephalosporin C to 7-A.C.A. Where R1 of Formula II is aralkyl substituted by NO2, the corresponding NH2 compound is produced by reducing the NO2 compound by catalytic hydrogenation. The above 7-aminocephalosporanic acid derivatives are effective against penicillinase-producing staphylococci and may be formulated into pharmaceutical and veterinary preparations (see Division A5).ALSO:A pharmaceutical or veterinary preparation comprises a carrier and a derivative of 7-aminocephalosporamic acid of formula II:- <FORM:1082962/A5-A6/1> in which R1 is aralkyl e.g. benzyl or substituted benzyl; R2 is carbamoyl, carboxy or alkoxycarbonyl and x is 1 or 2. The substituted benzyl may be of formula <FORM:1082962/A5-A6/2> wherein R3 is acyl or hydrogen, X is O or imino, R4 is alkoxy, alkylthio, acyl, carboxyalkyl, alkoxycarbonyloxy, nitro, alkyl or halogen; R5 is as R4 or hydrogen. The alkyl, alkanoyl and alkoxy contain 1-6C atoms. Typical compounds are N-(7-phenylacetamidoceph-3-em- 3 -ylmethyl)- 3\sv -carbamoyl pyridinium-4-carboxylate and N-(7-phenyl-acetamidoceph-3em-3yl methyl) 31-carboxy-pyridinium-4-carboxylate. The preparation may be an injection, tablet, capsule or oral liquid, a lotion, ointment or cream or veterinary cerate. Other antibiotics such as penicillins and/or the tetracyclines may be present.
GB2128463A 1963-05-28 1963-05-28 Derivatives of 7-aminocephalosporanic acid Expired GB1082962A (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
GB2128463A GB1082962A (en) 1963-05-28 1963-05-28 Derivatives of 7-aminocephalosporanic acid
NL646403229A NL140243B (en) 1963-05-28 1964-03-25 PROCESS FOR PREPARING 7 - ((SUBSTITUATED) PHENYLACETYLAMINO) -3- (1-PYRIDYLMETHYL) -3-CEFEM-4-CARBONIC ACID DERIVATIVES.
ES298060A ES298060A1 (en) 1963-05-28 1964-03-26 A procedure for the production of antibiotic compounds (Machine-translation by Google Translate, not legally binding)
DE19641445831 DE1445831C3 (en) 1963-05-28 1964-03-26 7-Phenylacetamido-cephalosporanic acid derivatives, processes for their preparation and pharmaceutical formulations
FR968973A FR1524027A (en) 1963-05-28 1964-03-27 7-aminocephalosporanic acid derivatives and process for their preparation
FR968974A FR4201M (en) 1963-05-28 1964-03-27
BE645868D BE645868A (en) 1963-05-28 1964-03-27
AT271664A AT261110B (en) 1963-05-28 1964-03-27 Process for the preparation of new derivatives of 7 aminocephalosporanic acid
CH405664A CH515274A (en) 1963-05-28 1964-03-31 7-Amino-cephalosporanic acid derivs. - useful as anti-bacterials

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2128463A GB1082962A (en) 1963-05-28 1963-05-28 Derivatives of 7-aminocephalosporanic acid

Publications (1)

Publication Number Publication Date
GB1082962A true GB1082962A (en) 1967-09-13

Family

ID=10160300

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2128463A Expired GB1082962A (en) 1963-05-28 1963-05-28 Derivatives of 7-aminocephalosporanic acid

Country Status (7)

Country Link
AT (1) AT261110B (en)
BE (1) BE645868A (en)
CH (1) CH515274A (en)
ES (1) ES298060A1 (en)
FR (1) FR4201M (en)
GB (1) GB1082962A (en)
NL (1) NL140243B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4012382A (en) * 1974-06-05 1977-03-15 Daniel Bouzard α-Amino and α-formyl-α-(p-acyloxyphenyl)acetamidocephalosporanic acid derivatives

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3118732A1 (en) * 1981-05-12 1982-12-02 Hoechst Ag, 6000 Frankfurt CEPHALOSPORINE DERIVATIVES AND METHOD FOR THEIR PRODUCTION

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4012382A (en) * 1974-06-05 1977-03-15 Daniel Bouzard α-Amino and α-formyl-α-(p-acyloxyphenyl)acetamidocephalosporanic acid derivatives

Also Published As

Publication number Publication date
FR4201M (en) 1966-06-06
ES298060A1 (en) 1964-09-01
NL6403229A (en) 1964-11-30
CH515274A (en) 1971-11-15
NL140243B (en) 1973-11-15
AT261110B (en) 1968-04-10
DE1445831B2 (en) 1976-04-08
DE1445831A1 (en) 1969-05-22
BE645868A (en) 1964-09-28

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