FI95256B - Förfarande för framställning av terapeutiskt användbara 2-substituerade-3-karboxikarbapenemer - Google Patents
Förfarande för framställning av terapeutiskt användbara 2-substituerade-3-karboxikarbapenemer Download PDFInfo
- 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
- Authority
- FI
- Finland
- Prior art keywords
- product
- oxo
- ethyl
- prepared
- chloro
- Prior art date
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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
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)
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)
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 |
-
1990
- 1990-04-10 US US07/507,271 patent/US5068232A/en not_active Expired - Fee Related
-
1991
- 1991-02-19 IL IL9727591A patent/IL97275A/en not_active IP Right Cessation
- 1991-02-21 EP EP19910102512 patent/EP0478874A3/en not_active Ceased
- 1991-02-26 TW TW080101501A patent/TW229209B/zh active
- 1991-02-28 IE IE067691A patent/IE910676A1/en unknown
- 1991-03-27 NZ NZ237610A patent/NZ237610A/en unknown
- 1991-04-04 CZ CS91929A patent/CZ280808B6/cs not_active IP Right Cessation
- 1991-04-04 SK SK929-91A patent/SK278900B6/sk unknown
- 1991-04-05 JP JP3102060A patent/JPH04234885A/ja active Pending
- 1991-04-08 PH PH42262A patent/PH27462A/en unknown
- 1991-04-08 CA CA002039968A patent/CA2039968A1/en not_active Abandoned
- 1991-04-09 NO NO911368A patent/NO178624C/no unknown
- 1991-04-09 FI FI911701A patent/FI95256C/sv active
- 1991-04-09 PT PT97301A patent/PT97301B/pt not_active IP Right Cessation
- 1991-04-09 KR KR1019910005684A patent/KR0183020B1/ko not_active IP Right Cessation
- 1991-04-09 AU AU74248/91A patent/AU634876B2/en not_active Ceased
- 1991-04-09 ZA ZA912629A patent/ZA912629B/xx unknown
- 1991-04-09 HU HU911141A patent/HU215606B/hu not_active IP Right Cessation
- 1991-04-10 CN CN91102357A patent/CN1034332C/zh not_active Expired - Fee Related
- 1991-04-10 PL PL91294072A patent/PL165952B1/pl unknown
- 1991-04-10 PL PL91289814A patent/PL166336B1/pl unknown
- 1991-04-10 PL PL91294071A patent/PL165937B1/pl unknown
-
1993
- 1993-07-06 US US08/087,944 patent/US5369102A/en not_active Expired - Lifetime
-
1994
- 1994-04-28 US US08/234,905 patent/US5480987A/en not_active Expired - Fee Related
- 1994-10-12 CN CN94116619A patent/CN1037177C/zh not_active Expired - Fee Related
- 1994-10-12 CN CN94116618A patent/CN1034329C/zh not_active Expired - Fee Related
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