GB1536288A - Method of preparation of 3-methylene-cephams - Google Patents

Method of preparation of 3-methylene-cephams

Info

Publication number
GB1536288A
GB1536288A GB51980/75A GB5198075A GB1536288A GB 1536288 A GB1536288 A GB 1536288A GB 51980/75 A GB51980/75 A GB 51980/75A GB 5198075 A GB5198075 A GB 5198075A GB 1536288 A GB1536288 A GB 1536288A
Authority
GB
United Kingdom
Prior art keywords
friedel
bronsted
compounds
crafts catalyst
acid type
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
GB51980/75A
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 GB1536288A publication Critical patent/GB1536288A/en
Expired legal-status Critical Current

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.
GB51980/75A 1974-12-24 1975-12-18 Method of preparation of 3-methylene-cephams Expired GB1536288A (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 (1)

Publication Number Publication Date
GB1536288A true GB1536288A (en) 1978-12-20

Family

ID=27065082

Family Applications (1)

Application Number Title Priority Date Filing Date
GB51980/75A Expired GB1536288A (en) 1974-12-24 1975-12-18 Method of preparation of 3-methylene-cephams

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) BG31072A4 (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) RO74273A (en)
SE (2) SE431547B (en)
SU (1) SU799667A3 (en)
YU (2) YU324875A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0109816A1 (en) * 1982-11-16 1984-05-30 Eli Lilly And Company N-substituted-2-(R)-(sulfinic acid)-3-(S)-(acylamido)-4-oxo-azetidines and process

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4289695A (en) * 1978-11-13 1981-09-15 Eli Lilly And Company Process for preparing 2-chlorosulfinylazetidinones
US4190724A (en) * 1978-11-13 1980-02-26 Eli Lilly And Company Process for 3-exomethylenecepham sulfoxides
GB2099817B (en) * 1981-04-10 1985-05-15 Otsuka Kagaku Yakuhin Azetidinone derivatives and process for the preparation of the same
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

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0109816A1 (en) * 1982-11-16 1984-05-30 Eli Lilly And Company N-substituted-2-(R)-(sulfinic acid)-3-(S)-(acylamido)-4-oxo-azetidines and process

Also Published As

Publication number Publication date
YU324875A (en) 1982-02-28
ATA980475A (en) 1977-06-15
JPS606960B2 (en) 1985-02-21
FR2333804A1 (en) 1977-07-01
IE42190B1 (en) 1980-06-18
FR2300080A1 (en) 1976-09-03
FR2300080B1 (en) 1979-06-15
DD124985A5 (en) 1977-03-23
NL182880C (en) 1988-06-01
SE431547B (en) 1984-02-13
YU206481A (en) 1983-06-30
HU177431B (en) 1981-10-28
NL182880B (en) 1988-01-04
BE837041A (en) 1976-06-23
DK585875A (en) 1976-06-25
BG27236A3 (en) 1979-09-14
PL114521B1 (en) 1981-02-28
CA1056372A (en) 1979-06-12
NL7515069A (en) 1976-06-28
SE7514550L (en) 1976-06-25
CH626604A5 (en) 1981-11-30
RO74273A (en) 1981-08-17
BG31072A4 (en) 1981-10-15
DD130933A5 (en) 1978-05-17
SE7906899L (en) 1979-08-17
RO68478A (en) 1981-08-30
DE2556045A1 (en) 1976-07-08
AT341672B (en) 1978-02-27
CH628620A5 (en) 1982-03-15
JPS5188992A (en) 1976-08-04
PL113883B1 (en) 1981-01-31
GR59922B (en) 1978-03-20
HU175226B (en) 1980-06-28
SU799667A3 (en) 1981-01-23
IL48565A (en) 1979-09-30
AR220505A1 (en) 1980-11-14
ES443829A1 (en) 1978-03-01
SE444810B (en) 1986-05-12
AU503202B2 (en) 1979-08-30
DE2556045C2 (en) 1990-08-09
DK157137B (en) 1989-11-13
IL48565A0 (en) 1976-01-30
DK157137C (en) 1990-04-16
IE42190L (en) 1976-06-24
FR2333804B1 (en) 1979-05-18
AU8708475A (en) 1977-06-02
CS191291B2 (en) 1979-06-29
CH625528A5 (en) 1981-09-30
ES457884A1 (en) 1978-08-16

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
704A Declaration that licence is not available as of right for an excepted use (par. 4a/1977)
PE20 Patent expired after termination of 20 years

Effective date: 19951217