FI95256B - Förfarande för framställning av terapeutiskt användbara 2-substituerade-3-karboxikarbapenemer - Google Patents

Förfarande för framställning av terapeutiskt användbara 2-substituerade-3-karboxikarbapenemer Download PDF

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Publication number
FI95256B
FI95256B FI911701A FI911701A FI95256B FI 95256 B FI95256 B FI 95256B FI 911701 A FI911701 A FI 911701A FI 911701 A FI911701 A FI 911701A FI 95256 B FI95256 B FI 95256B
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FI
Finland
Prior art keywords
product
oxo
ethyl
prepared
chloro
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Application number
FI911701A
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English (en)
Finnish (fi)
Other versions
FI911701A (sv
FI95256C (sv
FI911701A0 (sv
Inventor
Jr Carl B Ziegler
William V Curran
Gregg Feigelson
Original Assignee
American Cyanamid 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.)
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Publication date
Application filed by American Cyanamid Co filed Critical American Cyanamid Co
Publication of FI911701A0 publication Critical patent/FI911701A0/sv
Publication of FI911701A publication Critical patent/FI911701A/sv
Priority to FI943056A priority Critical patent/FI100328B/sv
Priority to FI943055A priority patent/FI100327B/sv
Publication of FI95256B publication Critical patent/FI95256B/sv
Application granted granted Critical
Publication of FI95256C publication Critical patent/FI95256C/sv

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D477/00—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring
    • C07D477/10—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with 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
    • C07D477/12—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with 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 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6
    • C07D477/14—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with 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 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 3
    • 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
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Communicable Diseases (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Oncology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Claims (4)

1. Förfarande för framställning av en terapeutiskt användbar 2-substituerad alkyl-3-karboxikarbapenemförening 5 med formeln :χψ: COjR3 COjRJ 10 (II) (III) eller
15 CChR3 (IV) (VI) i vilken R1 är 1-hydroxietyl vilken kan vara substituerad med en bensyloxikarbonyl- eller t-butyldimetylsilylgrupp,
20 R3 är p-metoxibensyl, p-nitrobensyl eller 2-klor- 2-propenyl eller en natrium- eller kaliumjon, X är H, varvid Y är fenylsulfonyl i vilken fenyl-gruppen kan vara substituerad med en eller tvä halogener, förgrenade eller linjära C^-alkyl- eller C^-alkoxigrupper 25 eller med en trifluormetyl- eller acylaminogrupp, tienyl-sulfonyl eller kinolinylsulfonyl, eller X är en halogen, varvid Y är en lägre alkoxikarbo-nyl, kännetecknat av, att en tri- eller tetra-substituerad allylazetidinon med formeln 30 : 1 x R N—/X / Π TXY (XVII) o 1 Q 35 cq2r3 » < 79 9 5 2 5 6 i vilken R1, R3 och X är ovan definierade, Q är en lämplig avgäende grupp, säsom en halogen, och
5 Y är en ovan definlerad elektroner tilldragande grupp, bringas att reagera i ett inert, vattenfritt, ap-rotiskt lösningsmedel med en icke-vattenhaltig bas vid en temperatur av ca -90 °C - 20 °C.
2. Förfarande enligt patentkrav 1, k ä n n e - 10 tecknat av att [2R-[2a,3(Z),5a,6a(R*)]]-3-(1-klor- 2- metoxi-2-oxoetyliden)-7-oxo-6- [1- [ [ (fenylmetoxi )karbo-nyl]oxi]etyl-l-azabicyklo[3.2.0]heptan-2-karboxylsyra,(4-nitrofenyl)metylester framställs.
3. Förfarande enligt patentkrav 1, k ä n n e - 15 tecknat av att [2R-[2a,3(R* eller S*),5a,6a(R*)]]- a-klor-2-[[(4-nitrofenyl)metoxi]karbonyl]-7-oxo-6-[ 1-[ [ (fenylmetoxi) karbonyl ] oxi] e tyl] -l-azabicyklo[3.2.0]hept- 3- en-3-ättikasyra, metylester framställs.
4. Förfarande enligt patentkrav 1, k ä n n e - 20 tecknat av att [2R-[2a,3(R* eller S*),5a,6a(R*)]]- 3-( l-klor-2-metoxi-2-oxoetyliden)-7-oxo-6- [l-[ [ (fenylmetoxi )karbonyl]oxi]etyl] -l-azabicyklo[3.2.0]heptan-2-karbo-xylsyra, (4-nitrofenyl)metylester framställs. » « s
FI911701A 1990-04-10 1991-04-09 Förfarande för framställning av terapeutiskt användbara 2-substituerade-3-karboxikarbapenemer FI95256C (sv)

Priority Applications (2)

Application Number Priority Date Filing Date Title
FI943056A FI100328B (sv) 1990-04-10 1994-06-23 Nya 4-allyl-2-oxo-1-azetidinättiksyraderivat
FI943055A FI100327B (sv) 1990-04-10 1994-06-23 Nya 4-propargyl-2-oxo-1-azetidinättiksyraderivat

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US07/507,271 US5068232A (en) 1990-04-10 1990-04-10 Novel 2-substituted alkyl-3-carboxy carbapenems as antibiotics and a method of producing them
US50727190 1990-04-10

Publications (4)

Publication Number Publication Date
FI911701A0 FI911701A0 (sv) 1991-04-09
FI911701A FI911701A (sv) 1991-10-11
FI95256B true FI95256B (sv) 1995-09-29
FI95256C FI95256C (sv) 1996-01-10

Family

ID=24017956

Family Applications (1)

Application Number Title Priority Date Filing Date
FI911701A FI95256C (sv) 1990-04-10 1991-04-09 Förfarande för framställning av terapeutiskt användbara 2-substituerade-3-karboxikarbapenemer

Country Status (20)

Country Link
US (3) US5068232A (sv)
EP (1) EP0478874A3 (sv)
JP (1) JPH04234885A (sv)
KR (1) KR0183020B1 (sv)
CN (3) CN1034332C (sv)
AU (1) AU634876B2 (sv)
CA (1) CA2039968A1 (sv)
CZ (1) CZ280808B6 (sv)
FI (1) FI95256C (sv)
HU (1) HU215606B (sv)
IE (1) IE910676A1 (sv)
IL (1) IL97275A (sv)
NO (1) NO178624C (sv)
NZ (1) NZ237610A (sv)
PH (1) PH27462A (sv)
PL (3) PL165952B1 (sv)
PT (1) PT97301B (sv)
SK (1) SK278900B6 (sv)
TW (1) TW229209B (sv)
ZA (1) ZA912629B (sv)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9104838D0 (en) * 1991-03-07 1991-04-17 Glaxo Spa Heterocyclic compounds
US5189158A (en) * 1991-03-20 1993-02-23 American Cyanamid Company 4-substituted azetidinones as precursors to 2-substituted-3-carboxy carbapenem antibiotics and a method of producing them
US5607928A (en) * 1994-08-05 1997-03-04 Zeneca Limited Carbapenem derivatives containing a bicyclic ketone substituent and their use as anti-infectives
EP0695753A1 (en) * 1994-08-05 1996-02-07 Zeneca Limited Carbapenem derivatives containing a bicyclic substituent, process for their preparation, and their use
DK0939632T3 (da) * 1996-02-23 2006-01-30 Lilly Co Eli Non-peptidyl vasopressin V1a antagonister
JP2004537032A (ja) * 2001-02-16 2004-12-09 ペプスキャン　システムズ　ベー．フェー． ピクセルアレイ
KR101328428B1 (ko) * 2004-06-10 2013-11-14 포브 신서시스 인코포레이티드 그램-음성 활성을 갖는 카바페넴 항균제 및 그의 제조방법
US20090018111A1 (en) * 2004-10-08 2009-01-15 Makoto Sunagawa Novel Antimicrobial Medicament
CN105884663B (zh) * 2016-04-27 2017-12-15 湖南科技学院 一种(z)‑磺酰基烯酸酯的制备方法
CN105906537B (zh) * 2016-04-27 2017-12-15 湖南科技学院 （z）式磺酰基烯酸酯化合物的一锅合成方法

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS56122379A (en) * 1980-03-03 1981-09-25 Sankyo Co Ltd 1-carba-2-penem-3-carboxylic acid derivative
US4350631A (en) * 1980-12-18 1982-09-21 Merck & Co., Inc. 6- and 4-Substituted-1-azabicyclo[3.2.0]heptan-3,7-dione-2-carboxylates
CA1179675A (en) * 1981-01-30 1984-12-18 Erwin Gotschi 7-oxo-1-azabicyclo ¬3,2,0| heptene-2-derivatives
JPS58103388A (ja) * 1981-12-11 1983-06-20 Sankyo Co Ltd カルバペネム誘導体
EP0171064B1 (en) * 1984-08-06 1995-07-12 Fujisawa Pharmaceutical Co., Ltd. Azetidinone derivative and processes for production thereof
EP0184844A1 (en) * 1984-12-13 1986-06-18 Merck & Co. Inc. 1-Methylcarbapenems having a 2-position substituent joined through an alkylenethio bridge
US4882429A (en) * 1986-03-03 1989-11-21 Schering Corporation Stereospecific preparation of (3S,4R,5R)-3-(1-hydroxyethyl)-4-benzoyloxy-azeridinones from L-(-)-theonine
IT1197873B (it) * 1986-10-15 1988-12-21 Erba Farmitalia Procedimento per la preparazione di azetidinoni
US5021565A (en) * 1986-10-16 1991-06-04 Merck & Co., Inc. Novel 2-substituted alkyl carbapenem antibacterials
EP0265117B1 (en) * 1986-10-16 1992-06-17 Merck & Co. Inc. 2-substituted alkyl carbapenem antibacterials
JPS63218659A (ja) * 1987-03-06 1988-09-12 Yasumitsu Tamura β−ラクタム化合物およびその製造法
JPH0193586A (ja) * 1987-10-05 1989-04-12 Yasumitsu Tamura カルバベネム化合物およびその製造法
US4960879A (en) * 1988-03-23 1990-10-02 Shionogi & Co., Ltd. Process for carbapenem intermediates
JPH0642853Y2 (ja) * 1988-10-28 1994-11-09 新王子製紙株式会社 プリンター
JPH03120280A (ja) * 1989-10-03 1991-05-22 Shionogi & Co Ltd ハロメチルカルバペネム化合物の製法

Also Published As

Publication number Publication date
HUT57770A (en) 1991-12-30
CN1056878A (zh) 1991-12-11
PL165937B1 (pl) 1995-03-31
NO178624C (no) 1996-05-02
CN1037177C (zh) 1998-01-28
EP0478874A2 (en) 1992-04-08
PL166336B1 (pl) 1995-05-31
NO178624B (no) 1996-01-22
CN1034332C (zh) 1997-03-26
AU634876B2 (en) 1993-03-04
FI911701A (sv) 1991-10-11
US5068232A (en) 1991-11-26
CZ280808B6 (cs) 1996-04-17
PT97301B (pt) 1998-08-31
NO911368D0 (no) 1991-04-09
IL97275A0 (en) 1992-05-25
TW229209B (sv) 1994-09-01
PL294071A1 (sv) 1993-02-08
US5369102A (en) 1994-11-29
CA2039968A1 (en) 1991-10-11
IE910676A1 (en) 1991-10-23
ZA912629B (en) 1992-01-29
CN1034329C (zh) 1997-03-26
FI95256C (sv) 1996-01-10
FI911701A0 (sv) 1991-04-09
KR0183020B1 (ko) 1999-05-01
CN1108648A (zh) 1995-09-20
AU7424891A (en) 1991-10-17
NZ237610A (en) 1995-02-24
NO911368L (no) 1991-10-11
CS92991A3 (en) 1992-04-15
IL97275A (en) 1996-01-31
PH27462A (en) 1993-07-09
PT97301A (pt) 1992-01-31
SK278900B6 (sk) 1998-04-08
HU911141D0 (en) 1991-10-28
CN1108649A (zh) 1995-09-20
US5480987A (en) 1996-01-02
KR910018384A (ko) 1991-11-30
EP0478874A3 (en) 1993-03-24
PL165952B1 (pl) 1995-03-31
PL289814A1 (en) 1992-08-10
JPH04234885A (ja) 1992-08-24
HU215606B (hu) 1999-01-28

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