IE39344L - 7ó-alkoxy cephalosporanates and corresponding¹penicillanates - Google Patents

7ó-alkoxy cephalosporanates and corresponding¹penicillanates

Info

Publication number
IE39344L
IE39344L IE740556A IE55674A IE39344L IE 39344 L IE39344 L IE 39344L IE 740556 A IE740556 A IE 740556A IE 55674 A IE55674 A IE 55674A IE 39344 L IE39344 L IE 39344L
Authority
IE
Ireland
Prior art keywords
butyl
benzyl
benzylideneamino
reacted
amino
Prior art date
Application number
IE740556A
Other versions
IE39344B1 (en
Original Assignee
Smithkline Corp
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 Smithkline Corp filed Critical Smithkline Corp
Publication of IE39344L publication Critical patent/IE39344L/en
Publication of IE39344B1 publication Critical patent/IE39344B1/en

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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Communicable Diseases (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Oncology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Cephalosporin Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1439898 Alkoxy-substituted cephalosporins and penicillins SMITHKLINE CORP 12 March 1974 [15 March 1973] 10871/74 Heading C2C A compound of the formula wherein R is hydrogen or acyl; R<SP>1</SP> is C 1-6 alkyl; Z is R<SP>2</SP> is hydrogen, or an easily removable ester protecting group; and A is a non-interfering group, is prepared (a) when R is H, by treating a compound of the formula wherein R<SP>3</SP> is C 1-6 alkyl, with a C 1-6 alkyl alcohol in the presence of a mercuric or silver ion in a compatible solvent at a temperature and for a length of time to cause substitution without decomposition, or (b) when R is acyl, treating a compound of the formula with a C 1-6 alkyl alcohol in the presence of a silver ion in a compatible solvent at a temperature and for a length of time to cause substitution without significant decomposition. Preparation of intermediates is described as follows: t-butyl 7#-benzylideneamino-desacetoxycephalosporanate is reacted with methyl methanethiosulphate and NaH to give t-butyl 7# - benzylideneamine - 7α - methylthiodesacetoxycephalosporanate which is treated with HC1 to form t-butyl 7#-amino-7α-methylthiodesacetoxycephalosporanate and its HCl salt; t-butyl 7#-aminocephalosporanate and benzaldehyde are reacted to form t-butyl 7#- benzylideneaminocephalosporanate which is reacted as above to form t-butyl 7#-benzylideneamino - 7α - methylthiocephalosporanate which is converted to t-butyl 7#-amino-7α- methylthiocephalosporanate; benzyl 6#- aminopenicillanate is similarly converted to benzyl 6# - benzylideneaminopenicillanate; benzyl 6# - benzylideneamino - 6α - methylthiopenicillanate; benzyl 6# - amino - 6α- methylthiopenicillanate and its p-toluenesulphonic acid salt. [GB1439898A]
IE556/74A 1973-03-15 1974-03-14 Method of preparing substituted cephalosporins and penicillins IE39344B1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US34142673A 1973-03-15 1973-03-15

Publications (2)

Publication Number Publication Date
IE39344L true IE39344L (en) 1974-09-15
IE39344B1 IE39344B1 (en) 1978-09-27

Family

ID=23337520

Family Applications (1)

Application Number Title Priority Date Filing Date
IE556/74A IE39344B1 (en) 1973-03-15 1974-03-14 Method of preparing substituted cephalosporins and penicillins

Country Status (8)

Country Link
JP (2) JPS6046116B2 (en)
BE (1) BE811314A (en)
CH (1) CH605976A5 (en)
DE (1) DE2412598C2 (en)
FR (1) FR2221455B1 (en)
GB (1) GB1439898A (en)
IE (1) IE39344B1 (en)
NL (1) NL7403515A (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4165429A (en) * 1976-06-28 1979-08-21 Yamanouchi Pharmaceutical Co., Ltd. 7α-METHOXY-CEPHALOSPORANIC ACID DERIVATIVES
ZA80905B (en) * 1979-03-01 1981-02-25 Beecham Group Ltd Penicillin derivatives
JO1395B1 (en) * 1981-07-10 1986-11-30 بيتشام جروب بي ال سي Process for the preparation of penam derivatives
JO1228B1 (en) * 1982-01-22 1985-04-20 بيتشام جروب بي ال سي Process for the preparation of penam derivatives
JPS6372698U (en) * 1986-10-28 1988-05-16

Also Published As

Publication number Publication date
FR2221455A1 (en) 1974-10-11
FR2221455B1 (en) 1978-07-07
CH605976A5 (en) 1978-10-13
JPS585199B2 (en) 1983-01-29
JPS6046116B2 (en) 1985-10-14
JPS49125390A (en) 1974-11-30
JPS5775985A (en) 1982-05-12
DE2412598A1 (en) 1974-09-26
DE2412598C2 (en) 1983-06-16
BE811314A (en) 1974-08-20
GB1439898A (en) 1976-06-16
IE39344B1 (en) 1978-09-27
NL7403515A (en) 1974-09-17

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