CS272234B2 - Method of 3-hydrocarbyl-3-cephaem derivative production - Google Patents

Method of 3-hydrocarbyl-3-cephaem derivative production Download PDF

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Publication number
CS272234B2
CS272234B2 CS882885A CS288588A CS272234B2 CS 272234 B2 CS272234 B2 CS 272234B2 CS 882885 A CS882885 A CS 882885A CS 288588 A CS288588 A CS 288588A CS 272234 B2 CS272234 B2 CS 272234B2
Authority
CS
Czechoslovakia
Prior art keywords
group
palladium
phosphine
ester
tri
Prior art date
Application number
CS882885A
Other languages
Czech (cs)
English (en)
Other versions
CS288588A2 (en
Inventor
Stephen R Baker
Vittorio Farina
Chester Sapino Jr
Original Assignee
Bristol Myers 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 to US07/019,395 priority Critical patent/US4847373A/en
Priority to US07/019,396 priority patent/US4870168A/en
Priority to IE117988A priority patent/IE64885B1/en
Priority to AU14758/88A priority patent/AU602395B2/en
Priority to FI881872A priority patent/FI91760C/fi
Priority to ZA882880A priority patent/ZA882880B/xx
Priority to FI881904A priority patent/FI94253C/fi
Priority to HU882083A priority patent/HU207521B/hu
Application filed by Bristol Myers Co filed Critical Bristol Myers Co
Priority to CS882885A priority patent/CS272234B2/cs
Priority to PT87367A priority patent/PT87367B/pt
Priority to EP88107887A priority patent/EP0342252A1/en
Priority to CA000564614A priority patent/CA1338644C/en
Priority to AU16515/88A priority patent/AU617669B2/en
Priority to CN88102961A priority patent/CN1035181C/zh
Priority to ES88108505T priority patent/ES2060619T3/es
Priority to DE3851749T priority patent/DE3851749T2/de
Priority to AT88108505T priority patent/ATE112571T1/de
Priority to EP88108505A priority patent/EP0343277B1/en
Priority to JP63130057A priority patent/JP2650716B2/ja
Priority to JP63134270A priority patent/JP2706090B2/ja
Priority to DD88327653A priority patent/DD280533A5/de
Priority to DD88316493A priority patent/DD270712A5/de
Publication of CS288588A2 publication Critical patent/CS288588A2/cs
Publication of CS272234B2 publication Critical patent/CS272234B2/cs

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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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • 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
    • 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
    • C07D501/22—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with radicals containing only hydrogen and carbon atoms, attached in position 3
    • 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
    • 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
    • C07D501/59—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3 with hetero atoms directly attached in position 3

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Communicable Diseases (AREA)
  • Animal Behavior & Ethology (AREA)
  • Oncology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Cephalosporin Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Medicinal Preparation (AREA)
  • Peptides Or Proteins (AREA)
CS882885A 1987-02-26 1988-04-28 Method of 3-hydrocarbyl-3-cephaem derivative production CS272234B2 (en)

Priority Applications (22)

Application Number Priority Date Filing Date Title
US07/019,395 US4847373A (en) 1987-02-26 1987-02-26 Production of 3-allyl- and 3-butenyl-3-cephems
US07/019,396 US4870168A (en) 1987-02-26 1987-02-26 3-Unsaturated alkyl cephems from 3-triflyl cephems
IE117988A IE64885B1 (en) 1987-02-26 1988-04-19 A process for the production of 3-hydrocarbyl-3-cephems
AU14758/88A AU602395B2 (en) 1987-02-26 1988-04-19 3-unsaturated alkyl cephems from 3-triflyl cephems
FI881872A FI91760C (fi) 1987-02-26 1988-04-21 Menetelmä terapeuttisesti käyttökelpoisten 7-substituoitujen asetamido-3-alkenyyli-3-kefeemijohdannaisten valmistamiseksi
ZA882880A ZA882880B (fi) 1987-02-26 1988-04-22
FI881904A FI94253C (fi) 1987-02-26 1988-04-22 Menetelmä 3-kefeemijohdannaisten valmistamiseksi
HU882083A HU207521B (en) 1987-02-26 1988-04-25 Process for producing 3-substituted 3-cepheme-derivatives
CS882885A CS272234B2 (en) 1987-02-26 1988-04-28 Method of 3-hydrocarbyl-3-cephaem derivative production
PT87367A PT87367B (pt) 1987-02-26 1988-04-29 Processo para a preparacao de derivados de alquil-cefem insaturados em posicao 3 a partir de novos compostos intermedios derivados de 3-triflil-cefem
EP88107887A EP0342252A1 (en) 1987-02-26 1988-05-17 3-allyl- and 3-butenyl-3-cephems and a process for the production thereof
CA000564614A CA1338644C (en) 1987-02-26 1988-05-18 Production of 3-allyl- and 3-butenyl-3-cephems
AU16515/88A AU617669B2 (en) 1987-02-26 1988-05-20 Production of 3-allyl- and 3-butenyl-3-cephems
CN88102961A CN1035181C (zh) 1987-02-26 1988-05-20 从3－三氟甲磺酰氧基头孢烯制备3－不饱和烃基头孢烯的方法
ES88108505T ES2060619T3 (es) 1987-02-26 1988-05-27 Un procedimiento para la produccion de 3-hidrocarbil-3-cefems.
DE3851749T DE3851749T2 (de) 1987-02-26 1988-05-27 Verfahren zur Herstellung von 3-hydrocarbyl-3-cephemverbindungen.
AT88108505T ATE112571T1 (de) 1987-02-26 1988-05-27 Verfahren zur herstellung von 3-hydrocarbyl-3- cephemverbindungen.
EP88108505A EP0343277B1 (en) 1987-02-26 1988-05-27 A process for the production of 3-hydrocarbyl-3-cephems
JP63130057A JP2650716B2 (ja) 1987-02-26 1988-05-27 ３−アリル及び３−ブテニル−３−セフェムの製造
JP63134270A JP2706090B2 (ja) 1987-02-26 1988-05-31 ３−トリフリルセフェムからの３−不飽和アルキルセフェム
DD88327653A DD280533A5 (de) 1987-02-26 1988-06-07 Verfahren zur herstellung von 3-trifluormethan-sulfonyloxy-3-cephem-zwischenverbindungen
DD88316493A DD270712A5 (de) 1987-02-26 1988-06-07 Verfahren zur herstellung von (hydrocarbyl)-3-cephem-derivaten

Applications Claiming Priority (16)

Application Number Priority Date Filing Date Title
US07/019,396 US4870168A (en) 1987-02-26 1987-02-26 3-Unsaturated alkyl cephems from 3-triflyl cephems
US07/019,395 US4847373A (en) 1987-02-26 1987-02-26 Production of 3-allyl- and 3-butenyl-3-cephems
IE117988A IE64885B1 (en) 1987-02-26 1988-04-19 A process for the production of 3-hydrocarbyl-3-cephems
AU14758/88A AU602395B2 (en) 1987-02-26 1988-04-19 3-unsaturated alkyl cephems from 3-triflyl cephems
FI881872A FI91760C (fi) 1987-02-26 1988-04-21 Menetelmä terapeuttisesti käyttökelpoisten 7-substituoitujen asetamido-3-alkenyyli-3-kefeemijohdannaisten valmistamiseksi
FI881904A FI94253C (fi) 1987-02-26 1988-04-22 Menetelmä 3-kefeemijohdannaisten valmistamiseksi
HU882083A HU207521B (en) 1987-02-26 1988-04-25 Process for producing 3-substituted 3-cepheme-derivatives
CS882885A CS272234B2 (en) 1987-02-26 1988-04-28 Method of 3-hydrocarbyl-3-cephaem derivative production
PT87367A PT87367B (pt) 1987-02-26 1988-04-29 Processo para a preparacao de derivados de alquil-cefem insaturados em posicao 3 a partir de novos compostos intermedios derivados de 3-triflil-cefem
CA000564614A CA1338644C (en) 1987-02-26 1988-05-18 Production of 3-allyl- and 3-butenyl-3-cephems
CN88102961A CN1035181C (zh) 1987-02-26 1988-05-20 从3－三氟甲磺酰氧基头孢烯制备3－不饱和烃基头孢烯的方法
EP88108505A EP0343277B1 (en) 1987-02-26 1988-05-27 A process for the production of 3-hydrocarbyl-3-cephems
JP63130057A JP2650716B2 (ja) 1987-02-26 1988-05-27 ３−アリル及び３−ブテニル−３−セフェムの製造
JP63134270A JP2706090B2 (ja) 1987-02-26 1988-05-31 ３−トリフリルセフェムからの３−不飽和アルキルセフェム
DD88327653A DD280533A5 (de) 1987-02-26 1988-06-07 Verfahren zur herstellung von 3-trifluormethan-sulfonyloxy-3-cephem-zwischenverbindungen
DD88316493A DD270712A5 (de) 1987-02-26 1988-06-07 Verfahren zur herstellung von (hydrocarbyl)-3-cephem-derivaten

Publications (2)

Publication Number Publication Date
CS288588A2 CS288588A2 (en) 1990-03-14
CS272234B2 true CS272234B2 (en) 1991-01-15

Family

ID=39688793

Family Applications (1)

Application Number Title Priority Date Filing Date
CS882885A CS272234B2 (en) 1987-02-26 1988-04-28 Method of 3-hydrocarbyl-3-cephaem derivative production

Country Status (16)

Country Link
US (2) US4870168A (fi)
EP (2) EP0342252A1 (fi)
JP (2) JP2650716B2 (fi)
CN (1) CN1035181C (fi)
AT (1) ATE112571T1 (fi)
AU (2) AU602395B2 (fi)
CA (1) CA1338644C (fi)
CS (1) CS272234B2 (fi)
DD (2) DD270712A5 (fi)
DE (1) DE3851749T2 (fi)
ES (1) ES2060619T3 (fi)
FI (2) FI91760C (fi)
HU (1) HU207521B (fi)
IE (1) IE64885B1 (fi)
PT (1) PT87367B (fi)
ZA (1) ZA882880B (fi)

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4874856A (en) * 1985-06-24 1989-10-17 Bristol-Myers Company 3-(substituted)propenyl-7-(aminothiazolylacetamido) ceph-3-em-4-carboxylic acids and esters thereof
GB8821797D0 (en) * 1988-09-16 1988-10-19 Beecham Group Plc Novel compounds
US5245027A (en) * 1989-11-21 1993-09-14 Bristol-Myers Squibb Company 3-fluorosulfonyloxyceph-3-em compounds
US5043439A (en) * 1990-03-08 1991-08-27 Bristol-Myers Squibb Company Process for production of cephalosporins
DE4030706A1 (de) * 1990-09-28 1992-04-02 Bayer Ag Neue 3-substituierte cephalosporine, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
US5106842A (en) * 1990-10-22 1992-04-21 Bristol-Myers Squibb Co. Antibiotic c-3 cyclobutenedione substituted (1-carba)cephalosporin compounds, compositions, and methods of use thereof
DE4037841A1 (de) * 1990-11-28 1992-06-04 Bayer Ag Neue 3-substituierte cephalosporine, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
AT396106B (de) * 1991-03-08 1993-06-25 Biochemie Gmbh Neues verfahren zur herstellung von 3-vinylcephalosporinverbindungen
PT630380E (pt) * 1992-02-05 2002-02-28 Biochemie Gmbh Processo para a purificacao de um derivado do acido 3-cefem-4-carboxilico
JP3224279B2 (ja) * 1992-07-27 2001-10-29 大塚化学株式会社 セフエム化合物の製造法
US5688786A (en) * 1994-04-01 1997-11-18 Microcide Pharmaceuticals, Inc. β-lactam antibiotics
US5698547A (en) * 1994-04-01 1997-12-16 Microcide Pharmaceuticals, Inc. Cephalosporin antibiotics
EP0754184A1 (en) * 1994-04-01 1997-01-22 Microcide Pharmaceuticals, Inc. Cephalosporin antibiotics
MY127641A (en) * 1995-10-12 2006-12-29 Essential Therapeutics Inc Cephalosporin antibiotics
US6025352A (en) * 1997-09-29 2000-02-15 Microcide Pharmaceuticals, Inc. Cephalosporin antibiotics
US6030965A (en) * 1997-09-30 2000-02-29 Microcide Pharmaceuticals, Inc. Cephalosporin antibiotics
JP4535530B2 (ja) * 1999-09-20 2010-09-01 大塚化学株式会社 ３−スルホニルオキシ−３−セフェム化合物の製造方法
TW500724B (en) 1999-10-05 2002-09-01 Pharmacia & Amp Upjohn Company Oxazinoquinolones useful for the treatment of viral infections
US6821969B2 (en) * 2001-02-13 2004-11-23 Pharmacia & Upjohn Company Thioxazinoquinolones as antiviral agents
WO2003050124A1 (en) * 2001-12-13 2003-06-19 Ranbaxy Laboratories Limited Crystalline cefdinir potassium dihydrate
EP1848724A2 (en) * 2005-10-31 2007-10-31 Teva Pharmaceutical Industries Ltd Process for the preparation of cefdinir
WO2007053722A2 (en) * 2005-10-31 2007-05-10 Teva Pharmaceutical Industries Ltd. Crystalline form of cefdinir cesium salt
EP2209474A4 (en) 2007-10-09 2013-07-24 Sopharmia Inc BROAD SPECTRUM BETA-LACTAMASE INHIBITORS
EP3441071A1 (en) 2013-03-12 2019-02-13 Gladius Pharmaceuticals Corporation Derivatized cephalosporins

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Publication number Priority date Publication date Assignee Title
US3769277A (en) * 1970-01-23 1973-10-30 Glaxo Lab Ltd Preparation of delta3-4 carboxy cephalosporins having a 3-vinyl or substituted 3-vinyl group
US3959324A (en) * 1972-04-26 1976-05-25 The Procter & Gamble Company Alkyltin cyclopropylcarbinylsulfonate
GB1377624A (en) * 1972-07-07 1974-12-18 Glaxo Lab Ltd Cephalosporin compounds
JPS543087A (en) * 1977-06-03 1979-01-11 Fujisawa Pharmaceut Co Ltd Preparation of cephalosporin compound
US4255423A (en) * 1977-07-27 1981-03-10 Merck & Co., Inc. Cephalosporin compounds
NZ198350A (en) * 1980-09-25 1985-02-28 Toyama Chemical Co Ltd Cephalosporins and intermediates;pharmaceutical compositions
JPS5758689A (en) * 1980-09-25 1982-04-08 Toyama Chem Co Ltd Novel preparation of 7-substituted or unsubstituted amino-3-substituted methylcephem carboxylic acids
US4537886A (en) * 1982-03-31 1985-08-27 Beecham Group P.L.C. β-lactam antibacterial agents and compositions containing them
US4609730A (en) * 1982-11-22 1986-09-02 Fujisawa Pharmaceutical Co., Ltd. 7-[substituted imino-2-(2-aminothiazol-4-yl)-acetamido]-3(2,2-dihalovinyl or ethynyl)-3-cephem-4-carboxylic acid (syn isomers), having antimicrobial activities
US4520022A (en) * 1983-01-28 1985-05-28 Bristol-Myers Company Substituted vinyl cephalosporins
FR2580652B1 (fr) * 1985-04-22 1989-01-06 Bristol Myers Co Acide 7-amino-3-propenylcephalosporanique et ses esters
US4708955A (en) * 1985-06-24 1987-11-24 Bristol-Myers Company 3-(substituted)propenyl-7-aminothiazol-ylcephalosporanic acids and esters thereof
US4619925A (en) * 1985-11-08 1986-10-28 Bristol-Myers Company 3-Propenyl cephalosporin derivatives
US4727070A (en) * 1985-11-25 1988-02-23 Bristol-Myers Company 3-Propenzl cephalosporin isomer separation process and derivative

Also Published As

Publication number Publication date
JP2706090B2 (ja) 1998-01-28
IE64885B1 (en) 1995-09-20
ZA882880B (fi) 1988-10-27
ES2060619T3 (es) 1994-12-01
ATE112571T1 (de) 1994-10-15
DE3851749D1 (de) 1994-11-10
AU1651588A (en) 1989-11-23
US4870168A (en) 1989-09-26
DD270712A5 (de) 1989-08-09
AU1475888A (en) 1989-10-26
EP0343277B1 (en) 1994-10-05
FI881904A0 (fi) 1988-04-22
FI91760B (fi) 1994-04-29
CA1338644C (en) 1996-10-15
FI881872A (fi) 1989-10-22
FI881904A (fi) 1989-10-23
HUT49885A (en) 1989-11-28
CS288588A2 (en) 1990-03-14
DE3851749T2 (de) 1995-02-09
HU207521B (en) 1993-04-28
PT87367A (pt) 1989-11-10
JP2650716B2 (ja) 1997-09-03
FI94253B (fi) 1995-04-28
JPH01313482A (ja) 1989-12-18
FI881872A0 (fi) 1988-04-21
CN1037709A (zh) 1989-12-06
EP0342252A1 (en) 1989-11-23
AU617669B2 (en) 1991-12-05
CN1035181C (zh) 1997-06-18
JPH01313483A (ja) 1989-12-18
FI94253C (fi) 1995-08-10
US4847373A (en) 1989-07-11
DD280533A5 (de) 1990-07-11
PT87367B (pt) 1994-04-29
EP0343277A1 (en) 1989-11-29
FI91760C (fi) 1994-08-10
AU602395B2 (en) 1990-10-11

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IF00 In force as of 2000-06-30 in czech republic
MK4A Patent expired

Effective date: 20080428