ES447577A1 - 4-thia-1-azabicyclo(4.2.0)oct-2-ene derivatives - Google Patents

4-thia-1-azabicyclo(4.2.0)oct-2-ene derivatives

Info

Publication number
ES447577A1
ES447577A1 ES447577A ES447577A ES447577A1 ES 447577 A1 ES447577 A1 ES 447577A1 ES 447577 A ES447577 A ES 447577A ES 447577 A ES447577 A ES 447577A ES 447577 A1 ES447577 A1 ES 447577A1
Authority
ES
Spain
Prior art keywords
formula
compounds
protective group
meaning stated
substituents
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
ES447577A
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.)
GlaxoSmithKline LLC
Original Assignee
SmithKline Corp
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 SmithKline Corp filed Critical SmithKline Corp
Publication of ES447577A1 publication Critical patent/ES447577A1/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
    • 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
    • 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
    • C07D205/085—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 nitrogen atom directly attached in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D263/36—One oxygen atom
    • C07D263/38—One oxygen atom attached in position 2
    • 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)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Cephalosporin Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Compounds of the formula I in which R and E have the meaning stated in Claim 1 are antibiotics which are effective against Gram-positive and Gram-negative bacteria. They are prepared by N-acylation of compounds of the formula II in which R<2> is hydrogen or a carboxyl protective group with compounds of the formula RX' in which X' has the meaning stated in Claim 1, and elimination of any carboxyl protective group present. During the reaction, intermediate protection of the sensitive substituents present in the radical R is also possible. The carboxylic acids of the formula II in which E is bromomethyl are prepared by bromination of compounds of the formula IV-b in which the substituents have the meaning stated in Claim 25 with a compound which provides bromine free radicals in the presence of an initiator which provides free radicals, with subsequent elimination of the amino protective group, or if E in the formula IV-b is a lower alkanoyloxymethyl group, by reaction of a compound of the formula VIII in which the substituents have the meaning stated in Claim 29 with a salt of a lower alkanecarboxylic acid and subsequent elimination of the amino protective group.
ES447577A 1975-05-05 1976-05-04 4-thia-1-azabicyclo(4.2.0)oct-2-ene derivatives Expired ES447577A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US57422575A 1975-05-05 1975-05-05
US62668675A 1975-10-29 1975-10-29

Publications (1)

Publication Number Publication Date
ES447577A1 true ES447577A1 (en) 1977-12-01

Family

ID=27076332

Family Applications (3)

Application Number Title Priority Date Filing Date
ES447577A Expired ES447577A1 (en) 1975-05-05 1976-05-04 4-thia-1-azabicyclo(4.2.0)oct-2-ene derivatives
ES460746A Expired ES460746A1 (en) 1975-05-05 1977-07-14 4-thia-1-azabicyclo(4.2.0)oct-2-ene derivatives
ES460722A Expired ES460722A1 (en) 1975-05-05 1977-07-14 4-thia-1-azabicyclo(4.2.0)oct-2-ene derivatives

Family Applications After (2)

Application Number Title Priority Date Filing Date
ES460746A Expired ES460746A1 (en) 1975-05-05 1977-07-14 4-thia-1-azabicyclo(4.2.0)oct-2-ene derivatives
ES460722A Expired ES460722A1 (en) 1975-05-05 1977-07-14 4-thia-1-azabicyclo(4.2.0)oct-2-ene derivatives

Country Status (11)

Country Link
JP (1) JPS51136694A (en)
AU (1) AU500636B2 (en)
CH (3) CH623331A5 (en)
DE (1) DE2619458A1 (en)
DK (1) DK194776A (en)
ES (3) ES447577A1 (en)
FR (2) FR2324639A1 (en)
GB (2) GB1553430A (en)
IE (1) IE43845B1 (en)
LU (1) LU74873A1 (en)
NL (1) NL7604797A (en)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4122086A (en) * 1977-07-26 1978-10-24 Smithkline Corporation Isopenicillins
FR2552089B2 (en) * 1981-05-13 1985-10-25 Roussel Uclaf NOVEL PRODUCTS DERIVED FROM 2-AMINO THIAZOLYL ACID 2-OXYIMINO ACETAMIDO BICYCLO-OCTENE CARBOXYLIC, THEIR PREPARATION PROCESS AND THEIR APPLICATION AS MEDICAMENTS
FR2505840A1 (en) * 1981-05-13 1982-11-19 Roussel Uclaf NOVEL PRODUCTS DERIVED FROM 2-AMINO THIAZOLYL 2-OXYIMINO ACETAMIDO BICYCLO-OCTENE CARBOXYLIC ACID, PROCESS FOR PREPARING THEM AND THEIR APPLICATION AS MEDICAMENTS
CA1262128A (en) * 1981-08-27 1989-10-03 Christian N. Hubschwerlen .beta.-lactams
FR2515182B1 (en) * 1981-10-23 1986-05-09 Roussel Uclaf NOVEL PRODUCTS DERIVED FROM 3-AMINO 2-OXO AZETIDINE 1-SULFAMIC ACID, THEIR PREPARATION PROCESS, THEIR APPLICATION AS MEDICAMENTS AND THE INTERMEDIATE PRODUCTS NECESSARY FOR THEIR PREPARATION
FR2538389B2 (en) * 1981-10-23 1986-05-16 Roussel Uclaf NEW PRODUCTS DERIVED FROM 3-AMINO 2-OXO AZETIDINE-1-SULFAMIC ACID, NEW PROCESS FOR THE PREPARATION OF OPTICALLY ACTIVE PRODUCTS, APPLICATION OF NEW PRODUCTS AS MEDICAMENTS AND PRODUCTS NECESSARY FOR THEIR PREPARATION
FR2558467B2 (en) * 1981-10-23 1987-03-20 Roussel Uclaf NEW PRODUCT DERIVED FROM 3-AMINO 2-OXO AZETIDINE 1-SULPHAMIC ACID, ITS PREPARATION PROCESS, ITS USE AS A MEDICAMENT AND AN INTERMEDIATE PRODUCT NECESSARY FOR ITS PREPARATION
JPS6036458A (en) * 1983-08-08 1985-02-25 Sumitomo Chem Co Ltd Preparation of beta-lactam derivative
FR2559486B1 (en) * 1984-02-13 1988-02-12 Roussel Uclaf NOVEL DERIVATIVES OF 1-DETHIA 2-THIA CEPHALOSPORANIC ACID, PROCESS FOR THEIR PREPARATION AND THEIR APPLICATION AS MEDICAMENTS
FR2586020B2 (en) * 1985-08-09 1988-10-14 Roussel Uclaf NOVEL DERIVATIVES OF 1-DETHIA 2-THIA CEPHALOSPORANIC ACID, PROCESS FOR THEIR PREPARATION, THEIR APPLICATION AS MEDICAMENTS AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
FR2588867B1 (en) * 1985-10-23 1988-12-09 Roussel Uclaf NOVEL PRODUCTS DERIVED FROM THE 3-AMINO 2-OXO AZETIDINE SERIES, THEIR PREPARATION PROCESS AND THEIR APPLICATION
FR2610630B2 (en) * 1987-02-06 1989-05-26 Roussel Uclaf NOVEL DERIVATIVES OF 1-DETHIA 2-THIA CEPHALOSPORANIC ACID, PROCESS FOR THEIR PREPARATION, THEIR USE AS MEDICAMENTS AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2046823A1 (en) * 1970-09-23 1972-03-30 Farbwerke Hoechst AG vormals Meister Lucius & Brüning, 6000 Frankfurt New azetidinones (2) and processes for their preparation

Also Published As

Publication number Publication date
GB1553429A (en) 1979-09-26
IE43845L (en) 1976-11-05
CH623331A5 (en) 1981-05-29
ES460746A1 (en) 1978-10-01
AU1366976A (en) 1977-11-10
AU500636B2 (en) 1979-05-31
IE43845B1 (en) 1981-06-17
CH627475A5 (en) 1982-01-15
FR2324639A1 (en) 1977-04-15
JPS51136694A (en) 1976-11-26
FR2313362B1 (en) 1979-03-23
DK194776A (en) 1976-11-06
FR2313362A1 (en) 1976-12-31
CH624670A5 (en) 1981-08-14
NL7604797A (en) 1976-11-09
FR2324639B1 (en) 1978-11-03
DE2619458A1 (en) 1976-11-18
LU74873A1 (en) 1977-01-12
ES460722A1 (en) 1978-05-01
GB1553430A (en) 1979-09-26

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