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FR2020209A1 - Antibiotic acylxymethyl 7-(alpha-amino-alpha-phenyl- - acetamido)-3-methyl-delta-3-cephem-4-carboxylates - Google Patents

Antibiotic acylxymethyl 7-(alpha-amino-alpha-phenyl- - acetamido)-3-methyl-delta-3-cephem-4-carboxylates

Info

Publication number
FR2020209A1
FR2020209A1 FR6934152A FR6934152A FR2020209A1 FR 2020209 A1 FR2020209 A1 FR 2020209A1 FR 6934152 A FR6934152 A FR 6934152A FR 6934152 A FR6934152 A FR 6934152A FR 2020209 A1 FR2020209 A1 FR 2020209A1
Authority
FR
France
Prior art keywords
alpha
amino
right arrow
convert
acylxymethyl
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.)
Withdrawn
Application number
FR6934152A
Other languages
French (fr)
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.)
SARATH
Original Assignee
SARATH
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 SARATH filed Critical SARATH
Publication of FR2020209A1 publication Critical patent/FR2020209A1/en
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • C07D501/22—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with radicals containing only hydrogen and carbon atoms, attached in position 3

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

Antibiotic acylxymethyl 7-(alpha-amino-alpha-phenylacetamido)-3-methyl-delta-3-cephem-4-c- arboxylates with improved absorption properties. G3A. Are new compounds of formula (I) (pref. stereoisomers being those of formula (II) and their mixtures), including their salts with non-toxic pharmaceutically acceptable acids:- (where alkyl, cycloalkyl, cycloalkylalkyl, aryl or aralkyl). Prepared by following methods:- 1) X-CH2OCOR 2) Convert R' into NH2 if necessary right arrow (I) (R' is NH2, substd. (i.e. protected) amino or a group convertible into NH2 (e.g. azido or nitro); Y is H or a cation; X is halogen, acyloxy, alkylsulphonyloxy or arylsulphonyloxy). 1) C6H5-CHR'-CO-Y' 2) convert R' into NH2 if necessary right arrow (I) (-CO-Y' is a group capable of reacting with the NH2 group to form a -CO-NH-bridge). oxidation (pref. H2O2 or metaperiodic acid) right arrow 1) Heat in inert solvent in presence of acid catalyst 2) Convert R' into NH2 if necessary right arrow (I).
FR6934152A 1968-10-09 1969-10-07 Antibiotic acylxymethyl 7-(alpha-amino-alpha-phenyl- - acetamido)-3-methyl-delta-3-cephem-4-carboxylates Withdrawn FR2020209A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB4792868 1968-10-09

Publications (1)

Publication Number Publication Date
FR2020209A1 true FR2020209A1 (en) 1970-07-10

Family

ID=10446763

Family Applications (1)

Application Number Title Priority Date Filing Date
FR6934152A Withdrawn FR2020209A1 (en) 1968-10-09 1969-10-07 Antibiotic acylxymethyl 7-(alpha-amino-alpha-phenyl- - acetamido)-3-methyl-delta-3-cephem-4-carboxylates

Country Status (3)

Country Link
CH (1) CH525241A (en)
DE (1) DE1951012A1 (en)
FR (1) FR2020209A1 (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2216288A1 (en) * 1973-02-07 1974-08-30 Politechnika Gdanska Cephalosporin acetoxymethyl esters - useful as antibacterials and cephalosporin inters
FR2459244A1 (en) * 1979-06-14 1981-01-09 Ausonia Farma Srl Prepn. of antibiotic pivcephalexine - by reaction of phenyl glycinyl chloride with a 7-isocyanato cephem carboxylic ester
FR2478103A1 (en) * 1980-03-14 1981-09-18 Dobfar Spa CEPHAPIRINE ESTERS, THEIR SALTS AND METHODS OF MAKING THE SAME

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1364672A (en) * 1971-06-09 1974-08-29 Beecham Group Ltd Penicillins
GB1406113A (en) * 1972-10-05 1975-09-17 Leo Pharm Prod Ltd Process for the preparation of cephalosporin estets
DE59200935D1 (en) * 1991-03-11 1995-01-26 Schweizerhall Saeurefab Process for the preparation of halogenated carboxylic acid esters.
ATE115114T1 (en) * 1991-03-11 1994-12-15 Schweizerhall Saeurefab PROCESS FOR THE PREPARATION OF CHLORINATED CARBONATE ESTERS.

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2216288A1 (en) * 1973-02-07 1974-08-30 Politechnika Gdanska Cephalosporin acetoxymethyl esters - useful as antibacterials and cephalosporin inters
FR2459244A1 (en) * 1979-06-14 1981-01-09 Ausonia Farma Srl Prepn. of antibiotic pivcephalexine - by reaction of phenyl glycinyl chloride with a 7-isocyanato cephem carboxylic ester
FR2478103A1 (en) * 1980-03-14 1981-09-18 Dobfar Spa CEPHAPIRINE ESTERS, THEIR SALTS AND METHODS OF MAKING THE SAME

Also Published As

Publication number Publication date
DE1951012A1 (en) 1970-04-23
CH525241A (en) 1972-07-15

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