ES455026A1 - Manufacture of semi-synthetic penicillin antibiotics - Google Patents

Manufacture of semi-synthetic penicillin antibiotics

Info

Publication number
ES455026A1
ES455026A1 ES455026A ES455026A ES455026A1 ES 455026 A1 ES455026 A1 ES 455026A1 ES 455026 A ES455026 A ES 455026A ES 455026 A ES455026 A ES 455026A ES 455026 A1 ES455026 A1 ES 455026A1
Authority
ES
Spain
Prior art keywords
acid chloride
semi
manufacture
penicillin antibiotics
compound
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
ES455026A
Other languages
Spanish (es)
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
Publication of ES455026A1 publication Critical patent/ES455026A1/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D499/21—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with a nitrogen atom directly attached in position 6 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
    • C07D499/44—Compounds with an amino radical acylated by carboxylic acids, attached in position 6
    • C07D499/48—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical
    • C07D499/58—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical
    • C07D499/64—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical by nitrogen atoms
    • C07D499/68—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical by nitrogen atoms with aromatic rings as additional substituents on the carbon chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D499/04—Preparation
    • C07D499/10—Modification of an amino radical directly attached in position 6
    • C07D499/12—Acylation

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Cephalosporin Compounds (AREA)

Abstract

In the synthesis of penicillin antibiotics by silylation of the carboxyl and, where appropriate, of the amino group of 6-aminopenicillanic acid, acylation with an acid chloride or protected acid chloride and subsequent elimination of the silyl groups, the silylation stage is carried out in an inert solvent using a compound of the formula: R<1>R<2>N-COR<3> (I) or R<1>N=C(OR<2>)R<3> (II> and in this way improved. A compound of the formula: < IMAGE > is formed and is, without isolation, reacted with the acid chloride or protected acid chloride. The meaning of the symbols is given in Claim 1.
ES455026A 1976-01-15 1977-01-14 Manufacture of semi-synthetic penicillin antibiotics Expired ES455026A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
IT47643/76A IT1053313B (en) 1976-01-15 1976-01-15 PROCEDURE FOR PRODUCING SEMI-SYNTHETIC ANTIBIOTICS

Publications (1)

Publication Number Publication Date
ES455026A1 true ES455026A1 (en) 1977-12-16

Family

ID=11261624

Family Applications (1)

Application Number Title Priority Date Filing Date
ES455026A Expired ES455026A1 (en) 1976-01-15 1977-01-14 Manufacture of semi-synthetic penicillin antibiotics

Country Status (14)

Country Link
JP (1) JPS5287191A (en)
AU (1) AU512150B2 (en)
BE (1) BE850382A (en)
CH (1) CH627182A5 (en)
DE (1) DE2701406A1 (en)
DK (1) DK13977A (en)
ES (1) ES455026A1 (en)
FR (1) FR2338279A1 (en)
GB (1) GB1569427A (en)
IT (1) IT1053313B (en)
NL (1) NL7700396A (en)
SE (1) SE437989B (en)
YU (1) YU9277A (en)
ZA (1) ZA77195B (en)

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB958478A (en) * 1962-03-13 1964-05-21 Beecham Res Lab Production of penicillins
FR68F (en) * 1962-10-17
US3351597A (en) * 1966-11-23 1967-11-07 Lilly Co Eli Process for acylating 7-amino cephalosporanic acid
ZA695612B (en) * 1968-08-23 1971-03-31 Lilly Co Eli Preparation of cephalosporin compounds
US3595855A (en) * 1968-12-05 1971-07-27 American Home Prod Process for producing aminopenicillins
IT1043957B (en) * 1970-12-31 1980-02-29 Lorenzini Sas Inst Biochim PROCESS FOR THE PREPARATION OF THE ANHYDROUS FORM OF ACID 6, D, LESS ALPINE AMINOPHENYLACETAMIDE PENICILLANIC
GB1494902A (en) * 1974-05-09 1977-12-14 Glaxo Lab Ltd Penicillins
IT1039495B (en) * 1975-06-26 1979-12-10 Dobfar Spa PROCEDURE FOR THE PREPARATION OF ANTIBIOTIC SUBSTANCES

Also Published As

Publication number Publication date
JPS5287191A (en) 1977-07-20
ZA77195B (en) 1977-11-30
NL7700396A (en) 1977-07-19
AU512150B2 (en) 1980-09-25
DE2701406A1 (en) 1977-07-21
IT1053313B (en) 1981-08-31
YU9277A (en) 1982-06-30
BE850382A (en) 1977-07-14
FR2338279B1 (en) 1980-09-05
SE7700393L (en) 1977-07-16
SE437989B (en) 1985-03-25
AU2134077A (en) 1978-07-20
DK13977A (en) 1977-07-16
GB1569427A (en) 1980-06-18
CH627182A5 (en) 1981-12-31
FR2338279A1 (en) 1977-08-12

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Legal Events

Date Code Title Description
FD1A Patent lapsed

Effective date: 19981103