DK170443B1 - Optisk aktive 5R,6S-6-(1R-hydroxyethyl)-2-(cis-1-oxo-3-thiolanylthio)-2-penem-3-carboxylsyreforbindelser samt mellemprodukter ved deres fremstilling - Google Patents

Optisk aktive 5R,6S-6-(1R-hydroxyethyl)-2-(cis-1-oxo-3-thiolanylthio)-2-penem-3-carboxylsyreforbindelser samt mellemprodukter ved deres fremstilling Download PDF

Info

Publication number
DK170443B1
DK170443B1 DK255888A DK255888A DK170443B1 DK 170443 B1 DK170443 B1 DK 170443B1 DK 255888 A DK255888 A DK 255888A DK 255888 A DK255888 A DK 255888A DK 170443 B1 DK170443 B1 DK 170443B1
Authority
DK
Denmark
Prior art keywords
hydrogen
formula
penem
give
reaction
Prior art date
Application number
DK255888A
Other languages
Danish (da)
English (en)
Other versions
DK255888D0 (da
DK255888A (da
Inventor
Robert Alfred Volkmann
Original Assignee
Pfizer
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 Pfizer filed Critical Pfizer
Publication of DK255888D0 publication Critical patent/DK255888D0/da
Publication of DK255888A publication Critical patent/DK255888A/da
Application granted granted Critical
Publication of DK170443B1 publication Critical patent/DK170443B1/da

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D499/86—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with only atoms other than nitrogen atoms directly attached in position 6 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/16—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by esterified hydroxyl radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
    • C07D333/28—Halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
    • C07D333/30—Hetero atoms other than halogen
    • C07D333/32—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
    • C07D333/30—Hetero atoms other than halogen
    • C07D333/34—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/46—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings substituted on the ring sulfur atom
    • C07D333/48—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings substituted on the ring sulfur atom by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D499/88—Compounds with a double bond between positions 2 and 3 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly 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)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Oncology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Communicable Diseases (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Epoxy Compounds (AREA)
  • Cephalosporin Compounds (AREA)
  • Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Steroid Compounds (AREA)
DK255888A 1987-05-11 1988-05-10 Optisk aktive 5R,6S-6-(1R-hydroxyethyl)-2-(cis-1-oxo-3-thiolanylthio)-2-penem-3-carboxylsyreforbindelser samt mellemprodukter ved deres fremstilling DK170443B1 (da)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US8701114 1987-05-11
PCT/US1987/001114 WO1988008845A1 (fr) 1987-05-11 1987-05-11 Acides diastereomeres 5r,6s-6-(1r-hydroxyethyle)-2-(cis-1-oxo-3-thiolanylthio)-2-penem-3-carboxyliques

Publications (3)

Publication Number Publication Date
DK255888D0 DK255888D0 (da) 1988-05-10
DK255888A DK255888A (da) 1989-02-07
DK170443B1 true DK170443B1 (da) 1995-09-04

Family

ID=22202388

Family Applications (1)

Application Number Title Priority Date Filing Date
DK255888A DK170443B1 (da) 1987-05-11 1988-05-10 Optisk aktive 5R,6S-6-(1R-hydroxyethyl)-2-(cis-1-oxo-3-thiolanylthio)-2-penem-3-carboxylsyreforbindelser samt mellemprodukter ved deres fremstilling

Country Status (27)

Country Link
US (2) US5013729A (fr)
EP (1) EP0294934B1 (fr)
JP (2) JPH0737463B2 (fr)
KR (1) KR900006840B1 (fr)
CN (2) CN1023016C (fr)
AT (1) ATE132869T1 (fr)
AU (1) AU603665B2 (fr)
CA (1) CA1338830C (fr)
CS (1) CS269999B2 (fr)
DD (1) DD270074A5 (fr)
DE (1) DE3854874T2 (fr)
DK (1) DK170443B1 (fr)
EG (1) EG18481A (fr)
ES (1) ES2081805T3 (fr)
FI (1) FI96423C (fr)
GR (1) GR3019094T3 (fr)
IE (1) IE70587B1 (fr)
IL (1) IL86288A0 (fr)
MA (1) MA21265A1 (fr)
MY (1) MY104306A (fr)
NZ (1) NZ224552A (fr)
PH (1) PH23931A (fr)
PL (1) PL159558B1 (fr)
PT (1) PT87443B (fr)
WO (1) WO1988008845A1 (fr)
YU (1) YU45059B (fr)
ZA (1) ZA883291B (fr)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0352977A3 (fr) * 1988-07-28 1991-08-07 Pfizer Inc. Procédé d'oxydation stéréosélectif
EP0382418A3 (fr) * 1989-02-09 1991-10-23 Pfizer Inc. Procédé de préparation d'esters thiolanyl-3 sulfonates optiquement actifs
US5321020A (en) * 1989-03-28 1994-06-14 Pfizer Inc. Antibacterial 2-carbapenem derivatives
HU209817B (en) * 1989-03-28 1994-11-28 Pfizer Process for the production of antibacterial 2-carbapenem derivatives
US5075439A (en) * 1990-08-17 1991-12-24 Pfizer Inc. Processes for (3S,4R)-3-[1(R)-t-butyl-dimethylsilyloxy)-ethyl]-4-[1-oxo-3-thiolanylthio(thiocarbonyl)thio]azetidin-2-ones and intermediates therefor
EP1712633A1 (fr) * 2003-12-02 2006-10-18 Mercian Corporation Procede de production de derives de tetrahydrothiophene optiquement actif et procede de cristallisation de tetrahydrothiopen-3-ol optiquement actif
JP2005314374A (ja) * 2004-03-31 2005-11-10 Daiso Co Ltd ３−ヒドロキシチオランの新規製法
KR100939347B1 (ko) 2005-07-20 2010-01-29 (주)카이로드 광학적으로 순수한 (ｓ)-3-히드록시 피롤리딘의 제조방법
PE20080940A1 (es) 2006-06-28 2008-07-09 Pfizer Prod Inc Profarmacos de penem
CN101479279B (zh) * 2006-06-28 2011-08-17 辉瑞产品公司 培南前药
US20080125408A1 (en) * 2006-11-14 2008-05-29 Pfizer Inc Penem prodrug
WO2008059367A1 (fr) * 2006-11-14 2008-05-22 Pfizer Products Inc. Promédicaments de sulopénème
JP2010536385A (ja) 2007-08-24 2010-12-02 コデクシス， インコーポレイテッド （ｒ）−３−ヒドロキシチオランの立体選択的生成のための改善されたケトレダクターゼポリペプチド
CN105061394A (zh) * 2015-09-11 2015-11-18 北京工商大学 一种2-丙基-4-乙酰氧基四氢噻吩的制备方法
EP4382529A1 (fr) 2022-12-07 2024-06-12 Bayer Consumer Care AG Procédé de préparation de (3s)-pyrrolidin-3-ol pur et de chlorhydrate de (3s)-pyrrolidin-3-ol pur

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4619924A (en) * 1984-05-18 1986-10-28 Pfizer Inc. 2-alkylthiopenem derivatives
EP0130025B1 (fr) * 1983-06-21 1987-07-08 Pfizer Inc. Dérivés de 2-alkylthiopénème
US4739047A (en) * 1985-10-17 1988-04-19 Pfizer Inc. Intermediates for 2-(1-oxo-3-thiolanyl)-2-penem antibiotics
ZA867809B (en) * 1985-10-17 1988-05-25 Pfizer Process for 2-(1-oxo-3-thiolanyl)-2-penem antibiotics
EP0223397B1 (fr) * 1985-10-17 1991-09-04 Pfizer Inc. Procédé pour préparer des antibiotiques dérivés du 2-(1-oxo-3-thiolanyl)-2-pénème
US4806637A (en) * 1986-03-17 1989-02-21 Schering Corporation 6-(Hydroxyethyl)-2-(heterocyclylthio)-penem-3-carboxylates
US4695626A (en) * 1986-07-29 1987-09-22 Pfizer Inc. 1-aza-4,5-dithiabicyclo [4.2.0] oct-2-en-8-one-2 carboxylate esters
PH24872A (en) * 1986-08-25 1990-12-26 Schering Corp (5r,6s,8r)-6-(-1-hydroxyethyl)-2-(3r-pyrrolidin-2-one-3-yl)thiopenem-3-carboxylic acid

Also Published As

Publication number Publication date
CS269999B2 (en) 1990-05-14
CN1073442A (zh) 1993-06-23
JP2544902B2 (ja) 1996-10-16
YU45059B (en) 1991-06-30
PL159558B1 (pl) 1992-12-31
GR3019094T3 (en) 1996-05-31
FI96423B (fi) 1996-03-15
CN1036996C (zh) 1998-01-14
EP0294934A2 (fr) 1988-12-14
EP0294934B1 (fr) 1996-01-10
FI895369A0 (fi) 1989-11-10
ES2081805T3 (es) 1996-03-16
MA21265A1 (fr) 1988-12-31
ZA883291B (en) 1989-12-27
IL86288A0 (en) 1988-11-15
PL272358A1 (en) 1989-10-30
DE3854874T2 (de) 1996-05-23
NZ224552A (en) 1989-10-27
PH23931A (en) 1990-01-23
EP0294934A3 (en) 1989-01-25
US5319103A (en) 1994-06-07
DD270074A5 (de) 1989-07-19
ATE132869T1 (de) 1996-01-15
DK255888D0 (da) 1988-05-10
WO1988008845A1 (fr) 1988-11-17
FI96423C (fi) 1996-06-25
JPH07278137A (ja) 1995-10-24
PT87443B (pt) 1992-08-31
YU90688A (en) 1989-12-31
KR880013943A (ko) 1988-12-22
AU603665B2 (en) 1990-11-22
CN88102863A (zh) 1988-12-21
AU1589688A (en) 1988-11-17
EG18481A (en) 1993-06-30
IE70587B1 (en) 1996-12-11
KR900006840B1 (ko) 1990-09-22
DE3854874D1 (de) 1996-02-22
CS311988A2 (en) 1989-08-14
JPS63287781A (ja) 1988-11-24
IE881411L (en) 1988-11-11
PT87443A (pt) 1989-05-31
DK255888A (da) 1989-02-07
JPH0737463B2 (ja) 1995-04-26
US5013729A (en) 1991-05-07
CA1338830C (fr) 1997-01-07
CN1023016C (zh) 1993-12-08
MY104306A (en) 1994-03-31

Similar Documents

Publication Publication Date Title
DK170443B1 (da) Optisk aktive 5R,6S-6-(1R-hydroxyethyl)-2-(cis-1-oxo-3-thiolanylthio)-2-penem-3-carboxylsyreforbindelser samt mellemprodukter ved deres fremstilling
Volkmann et al. 2-Thioalkyl penems: an efficient synthesis of sulopenem, a (5R, 6S)-6-(1 (R)-hydroxyethyl)-2-[(cis-1-oxo-3-thiolanyl) thio]-2-penem antibacterial
US4619924A (en) 2-alkylthiopenem derivatives
CZ58694A3 (en) Novel 2-thiosubstituted carbapenems, process of their preparation and pharmaceutical compositions based thereon
US4874877A (en) Process for optically active 3-(methane-sulfonyloxy)thiolane and analogs
JPS588084A (ja) （６ｒ）−置換−（５ｒ）−ペネム−３−カルボン酸誘導体およびその製造法
CA1246546A (fr) Derives de 2-alcoylthiopenem
FR2504533A1 (fr) Procede de preparation de composes de dioxolanylazetidinone et nouveaux produits ainsi obtenus, a activite antibacterienne
US5191077A (en) Diastereomeric 5R,6S-6-(1R-hydroxyethyl)-2-(cis-1-oxo-3-thiolanylthio)-2-penem-3-carboxylic acids
DK174484B1 (da) Fremgangsmåde til fremstilling af penemforbindelser samt azetidinon- penemforbindelser, der er anvendelige som mellemprodukter ved fremgangsmåden
PH27045A (en) Diastereomeric 5R 6S-6-(1R-hydroxyethyl)-2- (CIS-1-OXO-3- thiolanylthio)-2-penem-3-carboxylic acids
EP0223397B1 (fr) Procédé pour préparer des antibiotiques dérivés du 2-(1-oxo-3-thiolanyl)-2-pénème
IL103609A (en) Intermediates for the preparation of diastereomeric 5r ls-6-(1r-hydroxyethyl)-2-(cis-1-oxo-3-thiolanylthio)-2-penem-3-carboxylic acids
US4895940A (en) Process for the preparation of penems
US4794179A (en) 2-(1-oxo-3-thiolanyl)-2-penem antibiotics
HU204055B (en) Process for producing diastereomer 5r,6s-6-(1r-hydroxyethyl)-2-(cis-1-oxo-3-thiolanylthio)-2-penem-3-carboxylic acid derivatives
CA2224211A1 (fr) Syntheses de composes optiquement purs utiles en tant qu'inhibiteurs de garft et leurs intermediaires
HU194568B (en) Process for producing 2-/alkyl-thio/peneme derivatives
NO173654B (no) Analogifremgangsmaate for fremstilling av terapeutisk aktive diastereomere 5r,6s-6-(1r-hyrdroksyetyl)-2-(cis-1-okso-3-tiolanyltio)-2-penem-3-karboksylsyrer
JPH09136888A (ja) チオール化合物
CZ10593A3 (en) Derivatives of 2-hydroxy-3-sulfido-3-phenylpropionic acid, process for preparing such compounds and intermediates
NO175368B (no) Mellomprodukter for fremstilling av terapeutisk aktive diastereomere 5R,6S-6-(1R-hydroksyetyl)-2-(cis-1-okso-3-tiolanyltio)-2-penem-3-karboksylsyrer
NO180489B (no) Mellomprodukt som er et eventuelt beskyttet 5R, 6S-6-(1R-hydroksyetyl)-2-(1S-okso-3R tiolanyltio)-2-penem-3-karboksylsyrederivat

Legal Events

Date Code Title Description
B1 Patent granted (law 1993)
PBP Patent lapsed