GB1082943A - Derivatives of 7-aminocephalosporanic acid - Google Patents

Derivatives of 7-aminocephalosporanic acid

Info

Publication number
GB1082943A
GB1082943A GB1214363A GB1214363A GB1082943A GB 1082943 A GB1082943 A GB 1082943A GB 1214363 A GB1214363 A GB 1214363A GB 1214363 A GB1214363 A GB 1214363A GB 1082943 A GB1082943 A GB 1082943A
Authority
GB
United Kingdom
Prior art keywords
hydrogen
alkyl
hydroxy
formula
ylmethyl
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
GB1214363A
Inventor
Stephen Eardley
Alan Gibson Long
Wilfred Frank Wall
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 GB1214363A priority Critical patent/GB1082943A/en
Priority to NL6403230A priority patent/NL6403230A/xx
Priority to DEG40208A priority patent/DE1228264B/en
Priority to DE19641545922 priority patent/DE1545922A1/en
Priority to BE645869D priority patent/BE645869A/xx
Priority to FR968971A priority patent/FR1524026A/en
Priority to AT271764A priority patent/AT266312B/en
Priority to FR968972A priority patent/FR4200M/fr
Priority to CH405564A priority patent/CH531004A/en
Publication of GB1082943A publication Critical patent/GB1082943A/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

Landscapes

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

Abstract

The invention relates to derivatives of 7-aminocephalosporanic acid of formula <FORM:1082943/C2/1> in which R1 is hydrogen, halogen, alkoxy, alkythio, acyloxy, acyl, carboxyalkyl, carbamoyl, alkyl, hydroxy, nitro or amino; R2 is hydrogen, halogen, alkoxy, alkythio, acyloxy, acyl, carboxyalkyl, carbamoyl, alkyl, hydroxy, amino or substituted amino; R3 is hydrogen (except when R1 is hydrogen), alkyl, hydroxyalkyl, N-hydroxyalkylcarbamoyl, alkanoyloxy wherein the alkyl moieties contain not more than 4 C atoms; X is 1 or 2. Examples are N-(7-phenylacetamidoceph - 3 - em - 3 - ylmethyl)-21,41 - dimethyl pyridinium - 4 - carboxylate, N - (7 - phenylacetamido - ceph - 3 - em - 3 - ylmethyl) - 21 - methyl pyridinium - 4 - carboxylate, N - (7 - phenylacetamidoceph - 3 - em - 3 - ylmethyl) -21 - hydroxy - methylpyridinium - 4 - carboxylate and N - [7 - p - acetoxyphenylacetamido - ceph - 3 - em - 3 - ylmethyl] - 21 - methylpyridinium - 4 - carboxylate. The compounds are prepared by reacting a compound of formula <FORM:1082943/C2/2> or a water-soluble salt thereof, in a strongly polar medium with a compound of formula <FORM:1082943/C2/3> wherein R is hydrogen or <FORM:1082943/C2/4> and R1, R2, R3 and X have the above meanings; the resulting compound where R is hydrogen being phenylacetylated with an 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. A compound of Formula II where R1 is NH2 is obtained by reducing by catalytic hydrogenation a compound of Formula II where R1 is NO2. The 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-aminocephalosporanic acid of formula <FORM:1082943/A5-A6/1> in which R1 is hydrogen, halogen, alkoxy, alkylthio, acyloxy, acyl, carboxyalkyl, carbamoyl, alkyl, hydroxy, nitro or amino; R2 hydrogen, halogen, alkoxy, alkylthio, acyloxy, acyl, carboxyalkyl, carbamoyl, alkyl, hydroxy, amino or substituted amino; R3 is hydrogen (except when R1 is hydrogen), alkyl, hydroxyalkyl, N-hydroxy alkylcarbamoyl, alkanoyloxy wherein the alkyl moieties contain not more than 4C atoms; X is 1 or 2, e.g. N-(7-phenylacetamidoceph-3-em-3-ylmethyl)-2\sv,4\sv-dimethyl pyridinium-4-carboxylate. The preparation may be an injection, tablet, capsule or oral liquid, a lotion, ointment or cream or a veterinary cerate. Other antibiotics such as penicillins and/or the tetracyclines may be present.
GB1214363A 1963-03-27 1963-03-27 Derivatives of 7-aminocephalosporanic acid Expired GB1082943A (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
GB1214363A GB1082943A (en) 1963-03-27 1963-03-27 Derivatives of 7-aminocephalosporanic acid
NL6403230A NL6403230A (en) 1963-03-27 1964-03-25
DEG40208A DE1228264B (en) 1963-03-27 1964-03-26 Process for the preparation of derivatives of 7-phenylacetamidocephalosporanic acid of the C-type
DE19641545922 DE1545922A1 (en) 1963-03-27 1964-03-26 Process for the preparation of cephalosporin derivatives
BE645869D BE645869A (en) 1963-03-27 1964-03-27
FR968971A FR1524026A (en) 1963-03-27 1964-03-27 7-Aminocephalosporanic acid derivatives and process for their preparation
AT271764A AT266312B (en) 1963-03-27 1964-03-27 Process for the preparation of new derivatives of 7-acylamidocephalosporanic acids
FR968972A FR4200M (en) 1963-03-27 1964-03-27
CH405564A CH531004A (en) 1963-03-27 1964-03-31 7-Aminocephalo-sporadic acid derivs - having antibacterial activity

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB1214363A GB1082943A (en) 1963-03-27 1963-03-27 Derivatives of 7-aminocephalosporanic acid
GB2128563 1963-05-28

Publications (1)

Publication Number Publication Date
GB1082943A true GB1082943A (en) 1967-09-13

Family

ID=26248814

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1214363A Expired GB1082943A (en) 1963-03-27 1963-03-27 Derivatives of 7-aminocephalosporanic acid

Country Status (7)

Country Link
AT (1) AT266312B (en)
BE (1) BE645869A (en)
CH (1) CH531004A (en)
DE (2) DE1545922A1 (en)
FR (1) FR4200M (en)
GB (1) GB1082943A (en)
NL (1) NL6403230A (en)

Cited By (3)

* 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
KR100891720B1 (en) * 2007-09-13 2009-04-03 전남대학교산학협력단 4-carbamoylphenylacetic acid from pseudomonas chlororaphis o6 inducing systemic resistance against plant diseases, and uses thereof
WO2020099858A1 (en) * 2018-11-12 2020-05-22 Imperial College Of Science, Technology And Medicine Cephalosporin ciprofloxacin hybrid compounds

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1298904A (en) * 1959-03-16 1962-07-20 Nat Res Dev Process for the preparation of cephalosporin compounds
AT232645B (en) * 1960-01-20 1964-03-25 Nat Res Dev Process for the preparation of derivatives of 7-aminocephalosporanic acid u. similar links
NO122749B (en) * 1961-06-08 1971-08-09 Lilly Co Eli

Cited By (3)

* 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
KR100891720B1 (en) * 2007-09-13 2009-04-03 전남대학교산학협력단 4-carbamoylphenylacetic acid from pseudomonas chlororaphis o6 inducing systemic resistance against plant diseases, and uses thereof
WO2020099858A1 (en) * 2018-11-12 2020-05-22 Imperial College Of Science, Technology And Medicine Cephalosporin ciprofloxacin hybrid compounds

Also Published As

Publication number Publication date
FR4200M (en) 1966-06-06
NL6403230A (en) 1964-09-28
AT266312B (en) 1968-11-11
DE1228264B (en) 1966-11-10
DE1545922A1 (en) 1969-12-11
BE645869A (en) 1964-09-28
CH531004A (en) 1972-11-30

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