GB1315379A - 3-halomethyl-delta3-cephalosporin ester compounds - Google Patents

3-halomethyl-delta3-cephalosporin ester compounds

Info

Publication number
GB1315379A
GB1315379A GB4957870A GB4957870A GB1315379A GB 1315379 A GB1315379 A GB 1315379A GB 4957870 A GB4957870 A GB 4957870A GB 4957870 A GB4957870 A GB 4957870A GB 1315379 A GB1315379 A GB 1315379A
Authority
GB
United Kingdom
Prior art keywords
phosphorus
halomethyl
cephalosporin
amino
formula
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
GB4957870A
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
Priority claimed from US062699A external-priority patent/US3922268A/en
Application filed by Eli Lilly and Co filed Critical Eli Lilly and Co
Publication of GB1315379A publication Critical patent/GB1315379A/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
    • C07D501/02—Preparation
    • C07D501/04—Preparation from compounds already containing the ring or condensed ring systems, e.g. by dehydrogenation of the ring, by introduction, elimination or modification of substituents
    • 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

1315379 3-Halomethyl-cephalosporin esters ELI LILLY & CO 19 Oct 1970 [10 Aug 1970] 49578/70 Addition to 1295908 Headings C2A and C2C The invention comprises 3-halomethyl-#<SP>3</SP> cephalosporin esters of Formula II wherein R 1 is C 1 to C 6 alkanoyl, C 2 -C 6 chloroalkanoyl, or an acyl group of Formula III where Ar is 2-thienyl, wherein m is an integer of from 0 to 4, n is an integer of from 1 to 4, Z is oxygen or sulphur or a chemical bond, R<SP>3</SP> and R<SP>4</SP> are, separately, hydrogen or methyl, or when R<SP>3</SP> is hydrogen, R<SP>4</SP> can also be an N-protected amino group selected from N-tert-butoxycarbonylamino, N - (benzyloxycarbonyl) - amino, N - (allyloxycarbonyl) - amino, N - (cyclopentyloxycarbonylamino, and N - (2 - methoxycarbonyl-1-methylvinyl)-amino and n is 1; or when R<SP>4</SP> is N-protected amino as defined above, Ar can also be a group of Formula IV wherein Y is hydrogen or a substituent on the phenyl ring carbon atoms, such as fluorine, chlorine, bromine, iodine, C 1 -C 2 alkyl, C 1 -C 2 alkyloxy, N - protected - alpha - amino - C 1 - C 3 alkyl, butoxycarbonyl, nitro, cyano or trifluoromethyl, and w is an integer of from 1 to 2, X is chloro, bromo or iodo; and R<SP>1</SP> is 2,2,2-trichloroethyl, C 4 -C 6 tert-alkyl, C 5 -C 7 tertalkenyl, C 5 -C 7 -tert-alkynyl, benzyl, methoxybenzyl, nitrobenzyl, phenacyl, phthalimidomethyl or succinimidomethyl. A process for preparing compounds of Formula I or Formula II comprises reacting phosphorus trichloride, phosphorus tribromide, phosphorupentachloride, phosphorus oxychloride or phosphorus oxybromide with a 3-hydroxymethyls #<SP>3</SP>-cephalosporin sulphoxide ester in the presence of a tertiary amine in a substantially anhydrous liquid diluent at a temperature of from - 75‹ to 50‹ C. to form as product the following compounds: (1) 3-halomethyl-#<SP>3</SP>-cephalosporin ester from at least an equimolar amount of phosphorus trichloride or phosphorus tribromide when temperatures above - 25‹ C. are used, or (2) 3-halomethyl-#<SP>3</SP>-cephalosporin sulphoxide ester from an approximately equimolar amount of phosphorus tribromide or phosphorus trichloride when temperatures below -25‹ C. are used, or (3) 3-halomethyl-#<SP>3</SP>- cephalosporin sulphoxide ester from phosphorus pentachloride, phosphorus pentabromide, phosphorus oxychloride or phosphorus oxybromide.
GB4957870A 1970-08-10 1970-10-19 3-halomethyl-delta3-cephalosporin ester compounds Expired GB1315379A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US062699A US3922268A (en) 1969-12-08 1970-08-10 3-Halomethyl-{66 {hu 3-Cephalosporin esters

Publications (1)

Publication Number Publication Date
GB1315379A true GB1315379A (en) 1973-05-02

Family

ID=22044223

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4957870A Expired GB1315379A (en) 1970-08-10 1970-10-19 3-halomethyl-delta3-cephalosporin ester compounds

Country Status (5)

Country Link
CH (2) CH589659A5 (en)
DE (2) DE2065718A1 (en)
GB (1) GB1315379A (en)
HK (1) HK54876A (en)
MY (1) MY7600286A (en)

Also Published As

Publication number Publication date
CH589659A5 (en) 1977-07-15
MY7600286A (en) 1976-12-31
HK54876A (en) 1976-09-17
DE2065718A1 (en) 1975-07-17
CH598264A5 (en) 1978-04-28
DE2052531A1 (en) 1972-02-17

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Legal Events

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