ES8702887A1 - Procedimiento para la preparacion de acetidinonas (4r)-3,4- trans-disustituidas - Google Patents
Procedimiento para la preparacion de acetidinonas (4r)-3,4- trans-disustituidasInfo
- Publication number
- ES8702887A1 ES8702887A1 ES547464A ES547464A ES8702887A1 ES 8702887 A1 ES8702887 A1 ES 8702887A1 ES 547464 A ES547464 A ES 547464A ES 547464 A ES547464 A ES 547464A ES 8702887 A1 ES8702887 A1 ES 8702887A1
- Authority
- ES
- Spain
- Prior art keywords
- preparation
- optically active
- acyloxyazetidinones
- denotes hydrogen
- lower alkyl
- 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
Links
- 238000000034 method Methods 0.000 title abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- -1 (4R)-3,4-trans-disubstituted azetidinones Chemical class 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical group O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 abstract 1
- YZBQHRLRFGPBSL-RXMQYKEDSA-N carbapenem Chemical class C1C=CN2C(=O)C[C@H]21 YZBQHRLRFGPBSL-RXMQYKEDSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- HHXMXAQDOUCLDN-RXMQYKEDSA-N penem Chemical compound S1C=CN2C(=O)C[C@H]21 HHXMXAQDOUCLDN-RXMQYKEDSA-N 0.000 abstract 1
- 238000006798 ring closing metathesis reaction Methods 0.000 abstract 1
Classifications
-
- 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
- C07D303/48—Compounds containing oxirane rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. ester or nitrile radicals
-
- 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
- C07D205/09—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 sulfur atom directly attached in position 4
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Epoxy Compounds (AREA)
- Saccharide Compounds (AREA)
Abstract
PROCEDIMIENTO PARA LA OBTENCION DE AZETIDINONAS (4R)-3,4-TRANS-DISUSTITUIDAS, DE FORMULA (I). CONSISTE EN LA REACCION DE OXIDACION DE UN COMPUESTO DE FORMULA (II), POR TRATAMIENTO CON UN PERACIDO, SEGUN LA REACCION DE BAYER-WILLIGER, PARA FORMAR UN COMPUESTO DE FORMULA (I), EN LA QUE R1 REPRESENTA HIDROGENO O ALQUILO INFERIOR, R2 ES HIDROGENO O GRUPO PROTECTOR DE HIDROXI, R3 ES FENILO O ALQUILO Y R4 ES HIDROGENO O GRUPO PROTECTOR DE AMINO. LA REACCION SE LLEVA A CABO EN UN DISOLVENTE INERTE, A UNA TEMPERATURA COMPRENDIDA ENTRE 0JC Y 100JC. ESTOS COMPUESTOS TIENEN APLICACION COMO INTERMEDIOS PARA LA SINTESIS DE ANTIBIOTICOS.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH470084 | 1984-10-01 | ||
| CH51385 | 1985-02-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ES8702887A1 true ES8702887A1 (es) | 1987-01-16 |
| ES547464A0 ES547464A0 (es) | 1987-01-16 |
Family
ID=25684797
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES547464A Expired ES8702887A1 (es) | 1984-10-01 | 1985-10-01 | Procedimiento para la preparacion de acetidinonas (4r)-3,4- trans-disustituidas |
| ES557111A Expired ES8802380A1 (es) | 1984-10-01 | 1986-10-01 | Procedimiento para la preparacion de acilazetidinonas opticamente activas |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES557111A Expired ES8802380A1 (es) | 1984-10-01 | 1986-10-01 | Procedimiento para la preparacion de acilazetidinonas opticamente activas |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP0181831B1 (es) |
| JP (1) | JPH0616622A (es) |
| KR (1) | KR930005983B1 (es) |
| AT (1) | ATE93520T1 (es) |
| DE (1) | DE3587546D1 (es) |
| DK (1) | DK442285A (es) |
| ES (2) | ES8702887A1 (es) |
| FI (1) | FI84716C (es) |
| HU (2) | HU194821B (es) |
| IE (1) | IE60388B1 (es) |
| PT (1) | PT81226B (es) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62164689A (ja) * | 1986-01-14 | 1987-07-21 | Kanegafuchi Chem Ind Co Ltd | 新規β−ラクタム化合物及びその製造法 |
| US4861877A (en) * | 1984-07-05 | 1989-08-29 | Kanegafuchi Kagaku Kogyo Kabushiki Kaisha | Process for preparing 4-acetoxy-3-hydroxyethylazetidin-2-one derivatives |
| US4791198A (en) * | 1984-07-05 | 1988-12-13 | Kanegafuchi Kagaku Kogyo Kabushiki Kaisha | Beta-lactam compound and preparation thereof |
| EP0221846A1 (de) * | 1985-10-28 | 1987-05-13 | Ciba-Geigy Ag | Optisch aktive Acyloxyazetidinone |
| 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 |
| US4740595A (en) * | 1986-03-13 | 1988-04-26 | Schering Corporation | Preparation of azetidinones via N-protected oxirancecarboxamide intermediates |
| US4963670A (en) * | 1986-03-13 | 1990-10-16 | Schering Corporation | Preparation of azetidinones via novel protected intermediates |
| US4827006A (en) * | 1986-03-13 | 1989-05-02 | Schering Corporation | Preparation of azetidinones via novel protected intermediates |
| US5008404A (en) * | 1988-08-01 | 1991-04-16 | Schering Corporation | Preparation of azetidinones via novel protected intermediates |
| US5089609A (en) * | 1986-03-13 | 1992-02-18 | Schering Corporation | 4-benzoyl azetidinones |
| AU601180B2 (en) * | 1986-04-30 | 1990-09-06 | Kanegafuchi Kagaku Kogyo Kabushiki Kaisha | Process for preparing 4-acetoxy-3-hydroxyethylazetidin -2- one derivatives |
| EP0259268A1 (de) * | 1986-09-04 | 1988-03-09 | Ciba-Geigy Ag | Verfahren zur Herstellung optisch aktiver Beta-Lactame |
| IT1197873B (it) * | 1986-10-15 | 1988-12-21 | Erba Farmitalia | Procedimento per la preparazione di azetidinoni |
| GB8702139D0 (en) * | 1987-01-30 | 1987-03-04 | Ici Plc | Process |
| US5312914A (en) * | 1987-02-17 | 1994-05-17 | Ciba-Geigy Corp | Process for the manufacture of 4-acetoxy-3-hydroxyethyl-azetidinone |
| EP0279781A3 (de) * | 1987-02-17 | 1989-07-26 | Ciba-Geigy Ag | Verfahren zur Herstellung von 4-Acetoxy-3-hydroxyethyl-azetidinon |
| US5274188A (en) * | 1987-05-04 | 1993-12-28 | Ciba-Geigy Corporation | Process for the manufacture of 4-acyloxy-3-hydroxyethyl-azetidinones |
| EP0290385B1 (de) | 1987-05-04 | 1992-10-21 | Ciba-Geigy Ag | Neues Verfahren zur Herstellung von 4-Acyloxy-3-hydroxyethyl-azetidinonen |
| ATE89551T1 (de) * | 1988-11-04 | 1993-06-15 | Ciba Geigy Ag | Verfahren zur herstellung von optisch aktiven acyloxyazetidinonen. |
| US4876365A (en) * | 1988-12-05 | 1989-10-24 | Schering Corporation | Intermediate compounds for preparing penems and carbapenems |
| US4923982A (en) * | 1989-06-21 | 1990-05-08 | Merck & Co., Inc. | Oxidation and reduction method to produce 4-acyloxyazetidin-2-one |
| 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 |
| KR100205767B1 (ko) * | 1997-04-10 | 1999-07-01 | 이병언 | 아제티디논의 입체 선택적인 제조방법 |
| JP2008247889A (ja) * | 2007-03-05 | 2008-10-16 | Sumitomo Chemical Co Ltd | ε−カプロラクトン化合物の製造方法 |
| CN105001182B (zh) * | 2015-06-26 | 2017-08-25 | 上海应用技术学院 | 一种(2r,3r)‑n‑(苯甲酰基)甲基‑n‑4‑甲氧基苯基‑2,3‑环氧丁酰胺的制备方法 |
| CN114773378A (zh) * | 2022-04-28 | 2022-07-22 | 浙江工业大学 | 一种培南类药物中间体的非对映异构体的合成方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0042026B1 (de) * | 1978-02-02 | 1986-01-08 | Ciba-Geigy Ag | 3,4-Disubstituierte Azetidin-2-onverbindungen und Verfahren zu ihrer Herstellung |
| JPS55111463A (en) * | 1979-02-21 | 1980-08-28 | Sankyo Co Ltd | Beta-lactam compound and its preparation |
| JPS56142259A (en) * | 1980-03-11 | 1981-11-06 | Sankyo Co Ltd | Beta-lactam compound and its preparation |
| JPS6048964A (ja) * | 1983-08-26 | 1985-03-16 | Sankyo Co Ltd | 2−アゼチジノン誘導体及びその製造法 |
-
1985
- 1985-09-25 DE DE85810435T patent/DE3587546D1/de not_active Expired - Fee Related
- 1985-09-25 EP EP85810435A patent/EP0181831B1/de not_active Expired - Lifetime
- 1985-09-25 AT AT85810435T patent/ATE93520T1/de not_active IP Right Cessation
- 1985-09-27 FI FI853737A patent/FI84716C/fi not_active IP Right Cessation
- 1985-09-28 KR KR1019850007180A patent/KR930005983B1/ko not_active Expired - Fee Related
- 1985-09-30 IE IE240185A patent/IE60388B1/en not_active IP Right Cessation
- 1985-09-30 PT PT81226A patent/PT81226B/pt not_active IP Right Cessation
- 1985-09-30 DK DK442285A patent/DK442285A/da not_active Application Discontinuation
- 1985-10-01 HU HU853809A patent/HU194821B/hu not_active IP Right Cessation
- 1985-10-01 ES ES547464A patent/ES8702887A1/es not_active Expired
- 1985-10-01 HU HU85193A patent/HU198011B/hu not_active IP Right Cessation
-
1986
- 1986-10-01 ES ES557111A patent/ES8802380A1/es not_active Expired
-
1991
- 1991-08-08 JP JP3198195A patent/JPH0616622A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| HU198011B (en) | 1989-07-28 |
| HUT41005A (en) | 1987-03-30 |
| FI84716B (fi) | 1991-09-30 |
| KR930005983B1 (ko) | 1993-07-01 |
| ATE93520T1 (de) | 1993-09-15 |
| DK442285A (da) | 1986-04-02 |
| JPH0616622A (ja) | 1994-01-25 |
| PT81226B (pt) | 1988-01-22 |
| KR860003213A (ko) | 1986-05-21 |
| PT81226A (de) | 1985-10-01 |
| FI853737A0 (fi) | 1985-09-27 |
| DK442285D0 (da) | 1985-09-30 |
| EP0181831A2 (de) | 1986-05-21 |
| FI84716C (fi) | 1992-01-10 |
| HU194821B (en) | 1988-03-28 |
| DE3587546D1 (de) | 1993-09-30 |
| ES8802380A1 (es) | 1988-05-16 |
| IE852401L (en) | 1986-04-01 |
| EP0181831A3 (en) | 1986-08-13 |
| ES557111A0 (es) | 1988-05-16 |
| EP0181831B1 (de) | 1993-08-25 |
| HUT42437A (en) | 1987-07-28 |
| FI853737L (fi) | 1986-04-02 |
| IE60388B1 (en) | 1994-07-13 |
| ES547464A0 (es) | 1987-01-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FD1A | Patent lapsed |
Effective date: 19970519 |