GB1067644A - Antibiotic cephalosporin compounds and process for preparing same - Google Patents

Antibiotic cephalosporin compounds and process for preparing same

Info

Publication number
GB1067644A
GB1067644A GB3035764A GB3035764A GB1067644A GB 1067644 A GB1067644 A GB 1067644A GB 3035764 A GB3035764 A GB 3035764A GB 3035764 A GB3035764 A GB 3035764A GB 1067644 A GB1067644 A GB 1067644A
Authority
GB
United Kingdom
Prior art keywords
compounds
formula
thienyl
cephem
carboxylic acid
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
GB3035764A
Inventor
Edwin Harold Flynn
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.)
Eli Lilly and Co
Original Assignee
Eli Lilly and Co
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 Eli Lilly and Co filed Critical Eli Lilly and Co
Priority to GB3035764A priority Critical patent/GB1067644A/en
Publication of GB1067644A publication Critical patent/GB1067644A/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

Landscapes

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

Abstract

The invention relates to antibiotic cephalosporin compounds having the following formula and salts thereof with pharmaceutically acceptable acids; <FORM:1067644/C2/1> wherein R is a - or b -thienyl, a - or b -furyl; m and n are zero or 1; R1 is cyano, carboxy, carbamyl, N-methylcarbamyl, carbo (C1-C4) alkoxy, hydroxy or C1-C4 alkanoyl and R1 is attached to the 3- or 4-position of the pyridine ring. Specified salts are the hydrochloride, hydrobromide, sulphate, nitrate, orthophosphate and naphthalene - sulphonate. Typical compounds are 7-(a -thienyl acetamido)-3-(31-carbamylpyridinomethyl) - 3 - cephem - 4 - carboxylic acid and 7-(a -thienyl acetamido)-3-(41-cyanopyridinomethyl) - 3 - cephem - 4 - carboxylic acid. The compounds are prepared by heating a compound of formula <FORM:1067644/C2/2> or a water-soluble salt thereof, wherein R and n are as defined above; with a substituted pyridine of formula <FORM:1067644/C2/3> wherein R1 and m have the above meanings; in the presence of water, a pH of 3 to 8.5, preferably 6 to 7, and a temperature of 40 DEG to 100 DEG C. may be used. The compounds are non-toxic, effective against a broad range of pathogens, resistant to penicillinase and have a prolonged action on intramuscular injection. Pharmaceutical compositions comprise an excipient and at least one of the compounds of Formula I above.
GB3035764A 1964-07-31 1964-07-31 Antibiotic cephalosporin compounds and process for preparing same Expired GB1067644A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB3035764A GB1067644A (en) 1964-07-31 1964-07-31 Antibiotic cephalosporin compounds and process for preparing same

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3035764A GB1067644A (en) 1964-07-31 1964-07-31 Antibiotic cephalosporin compounds and process for preparing same

Publications (1)

Publication Number Publication Date
GB1067644A true GB1067644A (en) 1967-05-03

Family

ID=10306373

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3035764A Expired GB1067644A (en) 1964-07-31 1964-07-31 Antibiotic cephalosporin compounds and process for preparing same

Country Status (1)

Country Link
GB (1) GB1067644A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103755726A (en) * 2013-12-12 2014-04-30 福建省福抗药业股份有限公司 Cefalonium refinement purification method
CN103772415A (en) * 2013-12-31 2014-05-07 福建省福抗药业股份有限公司 Method for preparing cephalonium from 7-aminocephalosporanic acid at one step
CN104725403A (en) * 2015-03-04 2015-06-24 齐鲁晟华制药有限公司 Preparation method of cefalonium

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103755726A (en) * 2013-12-12 2014-04-30 福建省福抗药业股份有限公司 Cefalonium refinement purification method
CN103772415A (en) * 2013-12-31 2014-05-07 福建省福抗药业股份有限公司 Method for preparing cephalonium from 7-aminocephalosporanic acid at one step
CN104725403A (en) * 2015-03-04 2015-06-24 齐鲁晟华制药有限公司 Preparation method of cefalonium

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