IE37838B1 - Process for preparing a desacetoxycephalosporin compound and novel 3-nitrooxycepham compounds - Google Patents

Process for preparing a desacetoxycephalosporin compound and novel 3-nitrooxycepham compounds

Info

Publication number
IE37838B1
IE37838B1 IE1039/73A IE103973A IE37838B1 IE 37838 B1 IE37838 B1 IE 37838B1 IE 1039/73 A IE1039/73 A IE 1039/73A IE 103973 A IE103973 A IE 103973A IE 37838 B1 IE37838 B1 IE 37838B1
Authority
IE
Ireland
Prior art keywords
methyl
compound
carboxylate
cepham
phthalimido
Prior art date
Application number
IE1039/73A
Other versions
IE37838L (en
Original Assignee
Lilly Co Eli
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 Lilly Co Eli filed Critical Lilly Co Eli
Publication of IE37838L publication Critical patent/IE37838L/en
Publication of IE37838B1 publication Critical patent/IE37838B1/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
    • 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)
  • Cephalosporin Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1382947 Reacting 3-halocepham compounds ELI LILLY & CO 18 June 1973 [30 June 1972 (2)] 28800/73 Heading C2C A process for treating a cepham compound comprises reacting a cepham compound of Formula I with AgQ to obtain a mixture comprising a compound of Formula II a compound of Formula III and a compound of Formula IV wherein R is the residue of an imide derived from a dicarboxylic acid, R 1 is a carboxy protecting group, X is chlorine or bromine and Q is -ONO 2 or wherein R 2 is C 1-4 alkyl or C 5-6 cyclo-alkyl. The compound of Formula III may be converted by heating to 80 # 175‹ C. into the compound of Formula II. The following treatments are exemplified (1) the reaction between p-nitrobenzyl 7 - phthalimido - 3α - methyl - 3#- chlorocepham-4-carboxylate and silver nitrate to form a mixture of p-nitrobenzyl 7-phthalimido- 3α - methyl - 3# - nitroxycepham - 4 - carboxylate, p - nitrobenzyl 6 - phthalimido - 2amethyl - 2# - nitrooxymethyl penam - 3 - carboxylate and p-nitrobenzyl-7-phthalimido-3- methyl - 3 - cepham - 4 - carboxylate, (ii) modifications of (i) wherein the starting material is the p-methoxy- and not the p-nitro-cepham compound, (iii) p-methoxybenzyl 7-phthalimido- 3α - methyl - 3# - nitroxy cepham-4 - carboxylate prepared in (ii) is converted by heating to methoxybenzyl 7-phthalimido-3-methyl-3-cepham-4-carboxylate, (iv) modification of (i) wherein the starting material is the methyl and not the p-nitrobenzyl cepham compound, (v) methyl 7 - phthaleimido - 3α - methyl - 3#- nitro-oxycepham-4-carboxylate is converted by heating to methyl 7-phthalimido-3-methyl-3- cepham-4-carboxylate, and (vi) modification of (iv) wherein silver acetate is used instead of silver nitrate. [GB1382947A]
IE1039/73A 1972-06-30 1973-06-22 Process for preparing a desacetoxycephalosporin compound and novel 3-nitrooxycepham compounds IE37838B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US26779572A 1972-06-30 1972-06-30
US26785072A 1972-06-30 1972-06-30

Publications (2)

Publication Number Publication Date
IE37838L IE37838L (en) 1973-12-30
IE37838B1 true IE37838B1 (en) 1977-10-26

Family

ID=26952646

Family Applications (1)

Application Number Title Priority Date Filing Date
IE1039/73A IE37838B1 (en) 1972-06-30 1973-06-22 Process for preparing a desacetoxycephalosporin compound and novel 3-nitrooxycepham compounds

Country Status (8)

Country Link
JP (1) JPS4955686A (en)
CH (1) CH580634A5 (en)
DE (1) DE2333290A1 (en)
FR (1) FR2190828B1 (en)
GB (1) GB1382947A (en)
IE (1) IE37838B1 (en)
IL (1) IL42529A (en)
NL (1) NL7309169A (en)

Also Published As

Publication number Publication date
DE2333290A1 (en) 1974-01-03
FR2190828A1 (en) 1974-02-01
IE37838L (en) 1973-12-30
IL42529A (en) 1976-08-31
CH580634A5 (en) 1976-10-15
GB1382947A (en) 1975-02-05
IL42529A0 (en) 1973-08-29
NL7309169A (en) 1974-01-02
JPS4955686A (en) 1974-05-30
FR2190828B1 (en) 1978-01-06

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