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ES377938A1 - Procedure for preparing esters 3 - halogenometil - delta - cefalosporine or sulfoxides of them. (Machine-translation by Google Translate, not legally binding) - Google Patents

Procedure for preparing esters 3 - halogenometil - delta - cefalosporine or sulfoxides of them. (Machine-translation by Google Translate, not legally binding)

Info

Publication number
ES377938A1
ES377938A1 ES377938A ES377938A ES377938A1 ES 377938 A1 ES377938 A1 ES 377938A1 ES 377938 A ES377938 A ES 377938A ES 377938 A ES377938 A ES 377938A ES 377938 A1 ES377938 A1 ES 377938A1
Authority
ES
Spain
Prior art keywords
phosphorous
delta3
cephalosporin
halogenomethyl
ester
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
ES377938A
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.)
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
Publication of ES377938A1 publication Critical patent/ES377938A1/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

Landscapes

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

Abstract

Procedure for preparing 3-halogenomethyl-Delta3-cephalosporin or sulfoxide esters thereof, useful as intermediates in the production of antibiotics, and represented by the formulas **(See formula)** where X in each of formulas I and II is chlorine, bromine or iodine; R has the formula **(See formula)** where m is an integer from 0 to 4, n is an integer from 1 to 4, Z is oxygen or sulfur or a chemical bond, R3 and R4 are separately hydrogen or methyl, and Y is hydrogen or a substituent on carbon atoms of the phenyl ring such as fluorine, chlorine, bromine, iodine, C1 to C2 alkyl, C1 to C2 alkyloxy, N-protected alpha-aminoalkyl of C1 to C3, butoxycarbonyl, nitro, cyano, trifluoromethyl and Z is an integer from 1 to 2; and R1 is 2,2,2-trichlorethyl, C4 to C6 tertiary alkyl, C5 to C7 tertiaryalkenyl, C5 to C7 tertiaryalkynyl, benzyl, methoxybenzyl, nitrobenzyl, phenacyl, phthalimidomethyl, or succinimidomethyl; said process being characterized by reacting a phosphorous compound from groups (1) phosphorous trichloride or phosphorous tribromide, or (2) phosphorous pentachloride, phosphorous pentabromide, phosphorous oxychloride or phosphorous oxybromide with a 3-sulfoxide ester -hydroxymethyl-Delta3-cephalosporin, in the presence of a tertiary amine in a substantially anhydrous liquid diluent, at a temperature of about -75ºC to about 50ºC to form the corresponding (1) (a) ester of 3-halogenomethyl-Delta3- cephalosporin from at least an equimolar amount of phosphorous trichloride or phosphorous tribromide, when temperatures above about -25ºC or (1) (b) 3-halogenomethyl-Delta3-cephalosporin sulfoxide ester are used from a approximately equimolar amount of phosphorous tribromide or phosphorous trichloride, when temperatures below about -25ºC or (2) ester are used of 3-halogenomethyl-Delta3-cephalosporin sulfoxide from phosphorous pentachloride, phosphorous pentabromide, phosphorous oxychloride or phosphorous oxybromide. (Machine-translation by Google Translate, not legally binding)
ES377938A 1969-03-28 1971-03-25 Procedure for preparing esters 3 - halogenometil - delta - cefalosporine or sulfoxides of them. (Machine-translation by Google Translate, not legally binding) Expired ES377938A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US81164069A 1969-03-28 1969-03-28
US88323169A 1969-12-08 1969-12-08

Publications (1)

Publication Number Publication Date
ES377938A1 true ES377938A1 (en) 1973-01-01

Family

ID=27123508

Family Applications (1)

Application Number Title Priority Date Filing Date
ES377938A Expired ES377938A1 (en) 1969-03-28 1971-03-25 Procedure for preparing esters 3 - halogenometil - delta - cefalosporine or sulfoxides of them. (Machine-translation by Google Translate, not legally binding)

Country Status (14)

Country Link
JP (2) JPS5112635B1 (en)
BE (1) BE748055A (en)
CA (1) CA986094A (en)
CH (2) CH562828A5 (en)
DE (1) DE2065708C3 (en)
ES (1) ES377938A1 (en)
FR (1) FR2035977A1 (en)
GB (1) GB1295908A (en)
IE (1) IE34055B1 (en)
IL (1) IL34093A (en)
NL (1) NL7004479A (en)
PL (2) PL83186B1 (en)
RO (1) RO56339A (en)
SE (1) SE412237B (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE755256A (en) * 1969-08-26 1971-02-25 Glaxo Lab Ltd
IL59395A (en) 1979-03-06 1983-07-31 Gist Brocades Nv Bromo-substituted deacetoxycephalosporin derivatives and their preparation
JPS5832884A (en) * 1981-08-20 1983-02-25 Otsuka Chem Co Ltd Production of 3-exomethylenecepham derivative

Also Published As

Publication number Publication date
DE2065708B2 (en) 1977-10-20
PL83186B1 (en) 1975-12-31
IE34055B1 (en) 1975-01-22
GB1295908A (en) 1972-11-08
IE34055L (en) 1970-09-28
CA986094A (en) 1976-03-23
DE2065708C3 (en) 1978-06-08
IL34093A0 (en) 1970-05-21
PL92638B1 (en) 1977-04-30
BE748055A (en) 1970-09-28
JPS5112635B1 (en) 1976-04-21
NL7004479A (en) 1970-09-30
FR2035977A1 (en) 1970-12-24
IL34093A (en) 1975-10-15
CH564023A5 (en) 1975-07-15
DE2015317B2 (en) 1975-08-28
DE2065708A1 (en) 1975-04-10
JPS5136277B1 (en) 1976-10-07
CH562828A5 (en) 1975-06-13
DE2015317A1 (en) 1971-02-18
RO56339A (en) 1975-03-15
SE412237B (en) 1980-02-25

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