IE42190L - 3-methylenecephams. - Google Patents

3-methylenecephams.

Info

Publication number
IE42190L
IE42190L IE752596A IE259675A IE42190L IE 42190 L IE42190 L IE 42190L IE 752596 A IE752596 A IE 752596A IE 259675 A IE259675 A IE 259675A IE 42190 L IE42190 L IE 42190L
Authority
IE
Ireland
Prior art keywords
friedel
bronsted
compounds
crafts catalyst
acid type
Prior art date
Application number
IE752596A
Other versions
IE42190B1 (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 IE42190L publication Critical patent/IE42190L/en
Publication of IE42190B1 publication Critical patent/IE42190B1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
    • C07D205/09—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4
    • C07D205/095—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4 and with a nitrogen atom directly attached in position 3

Landscapes

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

Abstract

3-Methylenecepham 1-sulphoxides of the formula <IMAGE> in which the substituents are defined in Claim 1 are prepared. These compounds are prepared by bringing about ring closure in a corresponding sulphinylazetidinone of the formula <IMAGE> in which X is chlorine or bromine, an alcohol or thioalcohol residue, an ester or a thioester residue, or an amino radical. If X is chlorine or bromine, the compound II is reacted with a Friedel-Crafts catalyst of the Lewis acid type, with a Friedel-Crafts catalyst of the Bronsted protonic acid type or with a metathetical cation former in a dry inert organic solvent, or is dissolved in an organic Bronsted acid. If X in compounds II is an alcohol, thioalcohol, ester or thioester residue or an amino radical, reaction is carried out with a Friedel-Crafts catalyst of the Bronsted protonic acid type in a dry inert organic solvent, or the compound is dissolved in an organic Bronsted acid. The resulting compounds can be used for the preparation of cephem antibiotics. [GB1536288A]
IE2596/75A 1974-12-24 1975-11-28 Method of preparation of 3-methylenecephams IE42190B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US53628074A 1974-12-24 1974-12-24
US63273375A 1975-11-19 1975-11-19

Publications (2)

Publication Number Publication Date
IE42190L true IE42190L (en) 1976-06-24
IE42190B1 IE42190B1 (en) 1980-06-18

Family

ID=27065082

Family Applications (1)

Application Number Title Priority Date Filing Date
IE2596/75A IE42190B1 (en) 1974-12-24 1975-11-28 Method of preparation of 3-methylenecephams

Country Status (25)

Country Link
JP (1) JPS606960B2 (en)
AR (1) AR220505A1 (en)
AT (1) AT341672B (en)
AU (1) AU503202B2 (en)
BE (1) BE837041A (en)
BG (2) BG27236A3 (en)
CA (1) CA1056372A (en)
CH (3) CH625528A5 (en)
CS (1) CS191291B2 (en)
DD (2) DD124985A5 (en)
DE (1) DE2556045A1 (en)
DK (1) DK157137C (en)
ES (2) ES443829A1 (en)
FR (2) FR2333804A1 (en)
GB (1) GB1536288A (en)
GR (1) GR59922B (en)
HU (2) HU177431B (en)
IE (1) IE42190B1 (en)
IL (1) IL48565A (en)
NL (1) NL182880C (en)
PL (2) PL114521B1 (en)
RO (2) RO68478A (en)
SE (2) SE431547B (en)
SU (1) SU799667A3 (en)
YU (2) YU324875A (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4190724A (en) * 1978-11-13 1980-02-26 Eli Lilly And Company Process for 3-exomethylenecepham sulfoxides
US4289695A (en) * 1978-11-13 1981-09-15 Eli Lilly And Company Process for preparing 2-chlorosulfinylazetidinones
GB2099817B (en) * 1981-04-10 1985-05-15 Otsuka Kagaku Yakuhin Azetidinone derivatives and process for the preparation of the same
US4436596A (en) * 1982-11-16 1984-03-13 Eli Lilly And Company N-Substituted-2-(R)-(sulfinic acid)-3-(S)-(acylamido)-4-oxo-azetidines and process
DE4230053A1 (en) * 1992-09-08 1994-03-10 Pliva Handels Gmbh 4-oxo-azetidine-2-sulfonic acid amides and their salts, process for their preparation and their use

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3843682A (en) * 1972-05-15 1974-10-22 Lilly Co Eli 2-chlorosulfinyl-3-imido-azetedin-4-ones

Also Published As

Publication number Publication date
HU175226B (en) 1980-06-28
HU177431B (en) 1981-10-28
FR2300080B1 (en) 1979-06-15
PL113883B1 (en) 1981-01-31
IE42190B1 (en) 1980-06-18
FR2333804B1 (en) 1979-05-18
GB1536288A (en) 1978-12-20
RO68478A (en) 1981-08-30
SE7514550L (en) 1976-06-25
ES457884A1 (en) 1978-08-16
NL182880B (en) 1988-01-04
CS191291B2 (en) 1979-06-29
DK157137B (en) 1989-11-13
CA1056372A (en) 1979-06-12
GR59922B (en) 1978-03-20
YU206481A (en) 1983-06-30
AT341672B (en) 1978-02-27
SE444810B (en) 1986-05-12
AU8708475A (en) 1977-06-02
BG31072A4 (en) 1981-10-15
DD130933A5 (en) 1978-05-17
DD124985A5 (en) 1977-03-23
DK157137C (en) 1990-04-16
CH628620A5 (en) 1982-03-15
ES443829A1 (en) 1978-03-01
YU324875A (en) 1982-02-28
BE837041A (en) 1976-06-23
NL182880C (en) 1988-06-01
DK585875A (en) 1976-06-25
AR220505A1 (en) 1980-11-14
IL48565A (en) 1979-09-30
FR2300080A1 (en) 1976-09-03
SE7906899L (en) 1979-08-17
CH625528A5 (en) 1981-09-30
JPS606960B2 (en) 1985-02-21
JPS5188992A (en) 1976-08-04
DE2556045A1 (en) 1976-07-08
AU503202B2 (en) 1979-08-30
FR2333804A1 (en) 1977-07-01
CH626604A5 (en) 1981-11-30
RO74273A (en) 1981-08-17
PL114521B1 (en) 1981-02-28
IL48565A0 (en) 1976-01-30
SE431547B (en) 1984-02-13
BG27236A3 (en) 1979-09-14
DE2556045C2 (en) 1990-08-09
ATA980475A (en) 1977-06-15
NL7515069A (en) 1976-06-28
SU799667A3 (en) 1981-01-23

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