UA43331C2 - Спосіб асиметричного одержання флорфеніколу, спосіб регіовибіркового розкриття хірального епоксиду та спосіб одержання r, s- ізомеру флорфеніколу - Google Patents
Спосіб асиметричного одержання флорфеніколу, спосіб регіовибіркового розкриття хірального епоксиду та спосіб одержання r, s- ізомеру флорфеніколуInfo
- Publication number
- UA43331C2 UA43331C2 UA95073385A UA95073385A UA43331C2 UA 43331 C2 UA43331 C2 UA 43331C2 UA 95073385 A UA95073385 A UA 95073385A UA 95073385 A UA95073385 A UA 95073385A UA 43331 C2 UA43331 C2 UA 43331C2
- Authority
- UA
- Ukraine
- Prior art keywords
- obtaining
- florfenicol
- florfenikola
- assimetric
- isomer
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
-
- 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
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
Спосіб асиметричного отримання флорфеніколу формули (I) включає стадію регіовибіркового розкриття хірального епоксиду формули (II) шляхом послідовної обробки сильною основою, кислотою Л’юіса й діхлорацетонітрилом.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/993,932 US5352832A (en) | 1992-12-18 | 1992-12-18 | Asymmetric process for preparing florfenicol, thiamphenicol chloramphenicol and oxazoline intermediates |
PCT/US1993/012071 WO1994014764A1 (en) | 1992-12-18 | 1993-12-15 | Asymmetric process for preparing florfenicol, thiamphenicol, chloramphenicol and oxazoline intermediates |
Publications (1)
Publication Number | Publication Date |
---|---|
UA43331C2 true UA43331C2 (uk) | 2001-12-17 |
Family
ID=25540089
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
UA95073385A UA43331C2 (uk) | 1992-12-18 | 1993-12-15 | Спосіб асиметричного одержання флорфеніколу, спосіб регіовибіркового розкриття хірального епоксиду та спосіб одержання r, s- ізомеру флорфеніколу |
Country Status (20)
Country | Link |
---|---|
US (1) | US5352832A (uk) |
EP (1) | EP0674618B1 (uk) |
JP (1) | JP3428016B2 (uk) |
KR (1) | KR100284216B1 (uk) |
AT (1) | ATE170835T1 (uk) |
AU (1) | AU676003B2 (uk) |
CA (1) | CA2152089C (uk) |
CZ (1) | CZ287461B6 (uk) |
DE (1) | DE69320986T2 (uk) |
DK (1) | DK0674618T3 (uk) |
ES (1) | ES2120605T3 (uk) |
FI (1) | FI109295B (uk) |
HU (1) | HU225110B1 (uk) |
NO (1) | NO303575B1 (uk) |
NZ (1) | NZ259239A (uk) |
PL (1) | PL177891B1 (uk) |
RU (1) | RU2126383C1 (uk) |
SK (1) | SK281701B6 (uk) |
UA (1) | UA43331C2 (uk) |
WO (1) | WO1994014764A1 (uk) |
Families Citing this family (49)
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US5332835A (en) * | 1984-02-03 | 1994-07-26 | Zambon S.P.A. | Process for fluorinating 1-phenyl-2-amino-1,3-propanediol compounds and new oxazoline compounds useful in this process |
US5360811A (en) * | 1990-03-13 | 1994-11-01 | Hoechst-Roussel Pharmaceuticals Incorporated | 1-alkyl-, 1-alkenyl-, and 1-alkynylaryl-2-amino-1,3-propanediols and related compounds as anti-inflammatory agents |
DE4437932A1 (de) * | 1994-10-24 | 1996-04-25 | Bayer Ag | Verfahren zur Herstellung von in einer Seitenkette fluorierten Alkyloxazolen und neue, in einer Seitenkette fluorierte Alkyloxazole |
AU2247599A (en) * | 1997-09-24 | 1999-04-12 | Merck & Co., Inc. | Process of making 3-aryloxy, 4-aryl furan-2-ones useful as inhibitors of cox-2 |
EP1487785A2 (en) * | 2002-03-08 | 2004-12-22 | Schering-Plough Ltd. | Novel florfenicol-type antibiotics |
US7439268B2 (en) * | 2003-07-18 | 2008-10-21 | Idexx Laboratories | Compositions containing prodrugs of florfenicol and methods of use |
US20050049210A1 (en) * | 2003-08-27 | 2005-03-03 | Idexx Laboratories, Inc. | Methods for the controlled delivery of pharmacologically active compounds |
US7126005B2 (en) * | 2003-10-06 | 2006-10-24 | Aurobindo Pharma Limited | Process for preparing florfenicol |
RU2006126519A (ru) * | 2003-12-23 | 2008-01-27 | Шеринг-Плоу Лтд. (CH) | Пролекарствофлорфенилкола с улучшенной растворимостью в воде |
US7361689B2 (en) * | 2003-12-31 | 2008-04-22 | Schering-Plough Animal Health Corporation | Antibacterial 1-(4-mono- and di-halomethylsulphonylphenyl)-2-acylamino-3-fluoroproponals and preparation thereof |
PT1776109E (pt) * | 2004-08-13 | 2009-03-25 | Schering Plough Ltd | Formulação farmacêutica que compreende um antibiótico, um triazol e um corticosteróide |
BRPI0515917A (pt) | 2004-09-23 | 2008-08-12 | Schering Plough Ltd | controle de parasitas em animais pelo uso de novos derivados de éter de oxima de trifluorometanossulfonanilida |
JP4750126B2 (ja) * | 2004-11-19 | 2011-08-17 | シェーリング−プラウ・リミテッド | 殺寄生虫薬2−フェニル−3−(1h−ピロール−2−イル)アクリロニトリル誘導体の使用による動物における寄生虫の制御 |
PT1830885E (pt) * | 2004-12-21 | 2008-12-22 | Intervet Int Bv | Composição veterinária injectável |
AR054380A1 (es) * | 2005-06-09 | 2007-06-20 | Schering Plough Ltd | Control de parasitos en animales con derivados de n- ((feniloxi) fenil) -1,1,1-trifluorometansulfonamida y de n-(fenilsulfanil) fenil) -1,1,1-trifluorometansulfonamida |
US8119667B2 (en) * | 2005-12-29 | 2012-02-21 | Schering-Plough Animal Health Corporation | Carbonates of fenicol antibiotics |
US7518017B2 (en) | 2006-02-17 | 2009-04-14 | Idexx Laboratories | Fenicol compounds and methods synthesizing 2-trifluoroacetamido-3-substituted propiophenone compounds |
US20070238700A1 (en) * | 2006-04-10 | 2007-10-11 | Winzenberg Kevin N | N-phenyl-1,1,1-trifluoromethanesulfonamide hydrazone derivative compounds and their usage in controlling parasites |
MX2009006282A (es) * | 2006-12-13 | 2009-06-23 | Schering Plough Ltd | Profarmacos solubles en agua de florfenicol y sus analogos. |
US8044230B2 (en) * | 2006-12-13 | 2011-10-25 | Intervet Inc. | Water-soluble prodrugs of chloramphenicol, thiamphenicol, and analogs thereof |
US20090062397A1 (en) * | 2007-04-27 | 2009-03-05 | Schering-Plough Animal Health Corporation | Compounds and methods for enhancing solubility of florfenicol and structurally-related antibiotics using cyclodextrins |
TWI430995B (zh) | 2007-06-26 | 2014-03-21 | Du Pont | 萘異唑啉無脊椎有害動物控制劑 |
ES2666187T3 (es) | 2007-06-27 | 2018-05-03 | E. I. Du Pont De Nemours And Company | Procedimiento de control de plagas en animales |
US7550625B2 (en) * | 2007-10-19 | 2009-06-23 | Idexx Laboratories | Esters of florfenicol |
CN101909600A (zh) | 2007-11-09 | 2010-12-08 | 英特维特国际股份有限公司 | 速释固体制剂、其制备及其应用 |
TWI468407B (zh) | 2008-02-06 | 2015-01-11 | Du Pont | 中離子農藥 |
EP2321269B1 (en) | 2008-07-30 | 2018-09-19 | Intervet International B.V. | Process for preparing oxazoline-protected aminodiol compounds useful as intermediates to florfenicol |
CN101337916B (zh) * | 2008-08-12 | 2011-02-16 | 张家港市恒盛药用化学有限公司 | 氟苯尼考磺酸酯及其盐以及它们的制备方法 |
UA110924C2 (uk) | 2009-08-05 | 2016-03-10 | Е. І. Дю Пон Де Немур Енд Компані | Мезоіонні пестициди |
EP2461684A2 (en) | 2009-08-05 | 2012-06-13 | E. I. du Pont de Nemours and Company | Mesoionic pesticides |
UA107804C2 (en) | 2009-08-05 | 2015-02-25 | Du Pont | Mixtures of pesticides mezoionnyh |
AU2010279587A1 (en) | 2009-08-05 | 2012-02-09 | E. I. Du Pont De Nemours And Company | Mesoionic pesticides |
BRPI1002023A2 (pt) | 2010-03-01 | 2011-10-25 | Nanocore Biotecnologia S A | forma farmacêutica sólida de dissolução rápida para tratamento de infecções bacterianas |
MY156670A (en) | 2010-05-27 | 2016-03-15 | Du Pont | Crystalline form of 4-[5-[3-chloro-5-(trifluoromethly)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-n-[2-oxo-2-[(2,2,2-trifluoroethyl) amino]ethyl]-1-naphthalenecarboxamide |
CN101921214B (zh) * | 2010-08-03 | 2013-04-10 | 复旦大学 | 反式对甲砜基肉桂醇的合成方法 |
WO2012087630A1 (en) | 2010-12-20 | 2012-06-28 | E.I. Du Pont De Nemours And Company | Pyridine and pyrimidine compounds for controlling invertebrate |
US8969585B2 (en) * | 2011-01-31 | 2015-03-03 | Nagasaki University | Method for producing optically active compound or salt thereof |
CN102417472B (zh) * | 2011-12-12 | 2013-11-13 | 齐鲁动物保健品有限公司 | 一种氟苯尼考的制备方法 |
WO2013158422A1 (en) | 2012-04-17 | 2013-10-24 | E. I. Du Pont De Nemours And Company | Heterocyclic compounds for controlling invertebrate pests |
CN102827042B (zh) * | 2012-09-17 | 2013-11-06 | 湖北美天生物科技有限公司 | 氟苯尼考的手性合成方法 |
CN102863361B (zh) * | 2012-10-17 | 2014-03-12 | 湖北美天生物科技有限公司 | 甲砜霉素的手性催化合成方法 |
CN102911133B (zh) * | 2012-10-31 | 2014-07-02 | 绍兴民生医药有限公司 | (4r,5r)-2-二氯甲基-4,5-二氢-5-(4-甲砜基苯基)-4-恶唑甲醇的纯化方法 |
CN103336072A (zh) * | 2013-06-19 | 2013-10-02 | 湖北龙翔药业有限公司 | 一种测定氟苯尼考中手性活性成分含量的方法 |
CN103880719A (zh) * | 2014-03-27 | 2014-06-25 | 张家港威胜生物医药有限公司 | 一种制备氟苯尼考琥珀酸酯的方法 |
BR112016017141B1 (pt) * | 2014-04-16 | 2022-12-13 | Masteam Bio-Tech Co. Ltd | Método de síntese de florfenicol |
CN103980167B (zh) * | 2014-04-17 | 2016-06-08 | 天津大学 | 一种无定形氟苯尼考及其制备方法 |
CN106349130B (zh) * | 2016-08-25 | 2018-01-23 | 潍坊大有生物化工有限公司 | 一种新的氟苯尼考的合成方法 |
CN111153838B (zh) * | 2020-01-19 | 2021-08-24 | 浙江大学宁波理工学院 | 一种氟苯尼考的合成方法 |
CN113185473B (zh) * | 2021-06-30 | 2021-10-08 | 山东国邦药业有限公司 | 一种氟苯尼考中间体氟甲砜噁唑的制备方法 |
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US4235842A (en) * | 1978-10-27 | 1980-11-25 | Ryder International Corporation | Temperature cycle indicating means for a sterilizer unit |
ES8104203A1 (es) * | 1979-02-05 | 1981-04-16 | Schering Corp | Un procedimiento para la preparacion de un compuesto d-(treo-1-aril-2-acilamido-3-fluor-1-propanol |
US4235892A (en) * | 1979-02-05 | 1980-11-25 | Schering Corporation, Patent Dept. | 1-Aryl-2-acylamido-3-fluoro-1-propanols, methods for their use as antibacterial agents and compositions useful therefor |
US4361557A (en) * | 1980-01-28 | 1982-11-30 | Schering Corporation | 1-Aryl-2-acylamido-3-fluoro-1-propanol acylates, methods for their use as anti-bacterial agents and compositions useful therefor |
IT1173213B (it) * | 1984-02-03 | 1987-06-18 | Zambon Spa | Procedimento per fluorurare alcuni derivati dall'1l-fenil-2-ammino-1,3-propandiolo e loro intermedi |
US4900847A (en) * | 1985-04-04 | 1990-02-13 | Massachusetts Institute Of Technology | Catalytic asymmetric epoxidation |
US4876352A (en) * | 1988-09-14 | 1989-10-24 | Schering Corporation | Pressurized fluorination of hydroxy alkyl groups |
IT1237798B (it) * | 1989-10-20 | 1993-06-17 | Zambon Spa | Processo per l'inversione stereochimica di (2s,3s)-2-ammino-3-fenil-1 ,3-propandioli nei corrispondenti enantiomeri (2r,3r). |
CA2023600A1 (en) * | 1990-08-29 | 1992-02-23 | Wilfred P. Shum | Asymmetric epoxidation using a chiral hydroperoxide |
SK281740B6 (sk) * | 1990-10-25 | 2001-07-10 | Schering Corporation | Spôsob prípravy fluórfenikolu a jeho analógov |
WO1992007608A1 (en) * | 1990-10-31 | 1992-05-14 | Baxter International Inc. | Over-the-wire catheter |
CN1238112A (zh) * | 1996-09-16 | 1999-12-08 | 艾利森公司 | 使用号码可移动性数据库解决呼叫的来回往返 |
-
1992
- 1992-12-18 US US07/993,932 patent/US5352832A/en not_active Expired - Lifetime
-
1993
- 1993-12-15 NZ NZ259239A patent/NZ259239A/en not_active IP Right Cessation
- 1993-12-15 HU HU9501776A patent/HU225110B1/hu unknown
- 1993-12-15 CA CA002152089A patent/CA2152089C/en not_active Expired - Lifetime
- 1993-12-15 SK SK777-95A patent/SK281701B6/sk not_active IP Right Cessation
- 1993-12-15 DK DK94903599T patent/DK0674618T3/da active
- 1993-12-15 KR KR1019950702466A patent/KR100284216B1/ko active IP Right Grant
- 1993-12-15 AU AU57484/94A patent/AU676003B2/en not_active Expired
- 1993-12-15 AT AT94903599T patent/ATE170835T1/de active
- 1993-12-15 UA UA95073385A patent/UA43331C2/uk unknown
- 1993-12-15 ES ES94903599T patent/ES2120605T3/es not_active Expired - Lifetime
- 1993-12-15 DE DE69320986T patent/DE69320986T2/de not_active Expired - Lifetime
- 1993-12-15 PL PL93309393A patent/PL177891B1/pl unknown
- 1993-12-15 WO PCT/US1993/012071 patent/WO1994014764A1/en active IP Right Grant
- 1993-12-15 EP EP94903599A patent/EP0674618B1/en not_active Expired - Lifetime
- 1993-12-15 JP JP51523294A patent/JP3428016B2/ja not_active Expired - Lifetime
- 1993-12-15 CZ CZ19951598A patent/CZ287461B6/cs not_active IP Right Cessation
- 1993-12-15 RU RU95115555A patent/RU2126383C1/ru active
-
1995
- 1995-06-12 FI FI952872A patent/FI109295B/fi not_active IP Right Cessation
- 1995-06-16 NO NO19952425A patent/NO303575B1/no not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
AU676003B2 (en) | 1997-02-27 |
SK281701B6 (sk) | 2001-07-10 |
AU5748494A (en) | 1994-07-19 |
DE69320986D1 (de) | 1998-10-15 |
US5352832A (en) | 1994-10-04 |
NO952425D0 (no) | 1995-06-16 |
KR100284216B1 (ko) | 2001-04-02 |
FI109295B (fi) | 2002-06-28 |
JPH08504819A (ja) | 1996-05-28 |
CZ287461B6 (en) | 2000-11-15 |
NZ259239A (en) | 1996-04-26 |
ATE170835T1 (de) | 1998-09-15 |
RU2126383C1 (ru) | 1999-02-20 |
KR950704244A (ko) | 1995-11-17 |
ES2120605T3 (es) | 1998-11-01 |
JP3428016B2 (ja) | 2003-07-22 |
NO952425L (no) | 1995-06-16 |
PL177891B1 (pl) | 2000-01-31 |
FI952872A0 (fi) | 1995-06-12 |
CA2152089C (en) | 2006-10-24 |
DE69320986T2 (de) | 1999-03-04 |
EP0674618A1 (en) | 1995-10-04 |
EP0674618B1 (en) | 1998-09-09 |
HU9501776D0 (en) | 1995-08-28 |
CA2152089A1 (en) | 1994-07-07 |
FI952872A (fi) | 1995-06-12 |
NO303575B1 (no) | 1998-08-03 |
SK77795A3 (en) | 1995-12-06 |
WO1994014764A1 (en) | 1994-07-07 |
DK0674618T3 (da) | 1999-02-22 |
HU225110B1 (en) | 2006-06-28 |
PL309393A1 (en) | 1995-10-02 |
HUT72669A (en) | 1996-05-28 |
CZ159895A3 (en) | 1996-01-17 |
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