AR008298A1 - Proceso para preparar intermediarios de florfenicol y sus compuestos analogos - Google Patents
Proceso para preparar intermediarios de florfenicol y sus compuestos analogosInfo
- Publication number
- AR008298A1 AR008298A1 ARP970103736A ARP970103736A AR008298A1 AR 008298 A1 AR008298 A1 AR 008298A1 AR P970103736 A ARP970103736 A AR P970103736A AR P970103736 A ARP970103736 A AR P970103736A AR 008298 A1 AR008298 A1 AR 008298A1
- Authority
- AR
- Argentina
- Prior art keywords
- compound
- formula
- alkyl
- florphenicol
- intermediaries
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D263/28—Nitrogen atoms not forming part of a nitro radical
Abstract
Un proceso para preparar intermediarios de florfenicol ([R-(S*,S*)]-2, 2- dicloro-N-[1-(fluorometil)-2-hidroxi-2-[4-(metilsulfonil)fenil]etil]acetamida)de la fórmula (I) donde R es H, NO2, CH3S, CH3SO2, o C4 a C6 alquilo; y R es arilo, haloarilo, bencilo, bencilo sustituído, C1 a C6 alquilo C3 a C7cicloalquilo y haloalquilo, y la configuración del anillo oxasolidina es 4R trans: que comprende: a) conyactar un compuesto de fórmula II donde R es comose describe anteriormente, y Res H, C1 a C6 alquilo, C3 a C7 cicloalquilo, bencilo sustituído o arilo; con un agente reductor tal como borohidruro depotasio, en un recipiente de reacción adecuado, para obtener un compuesto de fórmula III dende R es como se describeanteriormente, y B9 luego reacciona enel mismo recipiente de reacción un compuesto de fórmula III, con un compuesto fórmula IV: para obtener un compuesto de fórmula I. Es un agente antibacterianode amplio espectro en el tratamiento de infeccionesde Gramm positivo , Gram negativos y ricketsia.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/699,271 US5663361A (en) | 1996-08-19 | 1996-08-19 | Process for preparing intermediates to florfenicol |
Publications (1)
Publication Number | Publication Date |
---|---|
AR008298A1 true AR008298A1 (es) | 1999-12-29 |
Family
ID=24808601
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ARP970103736A AR008298A1 (es) | 1996-08-19 | 1997-08-15 | Proceso para preparar intermediarios de florfenicol y sus compuestos analogos |
Country Status (31)
Country | Link |
---|---|
US (1) | US5663361A (es) |
EP (1) | EP0922040B2 (es) |
JP (1) | JP3274868B2 (es) |
KR (1) | KR100286851B1 (es) |
CN (1) | CN1097583C (es) |
AR (1) | AR008298A1 (es) |
AT (1) | ATE283847T1 (es) |
AU (1) | AU714495B2 (es) |
BR (1) | BR9711318B1 (es) |
CA (1) | CA2264116C (es) |
CO (1) | CO4560550A1 (es) |
CZ (1) | CZ297915B6 (es) |
DE (1) | DE69731835T3 (es) |
DK (1) | DK0922040T3 (es) |
ES (1) | ES2234026T5 (es) |
HK (1) | HK1017890A1 (es) |
HU (1) | HU229610B1 (es) |
ID (1) | ID18047A (es) |
IL (1) | IL128574A (es) |
MY (1) | MY115679A (es) |
NO (1) | NO312962B1 (es) |
NZ (1) | NZ334111A (es) |
PE (1) | PE99798A1 (es) |
PL (2) | PL196454B1 (es) |
PT (1) | PT922040E (es) |
SI (1) | SI0922040T1 (es) |
SK (1) | SK286124B6 (es) |
TR (2) | TR200800474T2 (es) |
TW (1) | TW381075B (es) |
WO (1) | WO1998007709A1 (es) |
ZA (1) | ZA977406B (es) |
Families Citing this family (40)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1173933C (zh) * | 2001-06-01 | 2004-11-03 | 中国科学院上海有机化学研究所 | 一种从l型取代苯丝氨酸酯制备d-(-)-苏式1-r-取代苯基-2-二氯乙酰氨基-3-氟-1-丙醇的方法 |
BR0308289A (pt) * | 2002-03-08 | 2005-01-11 | Schering Plough Ltd | Antibióticos do tipo florfenicol |
TW200505425A (en) * | 2003-05-29 | 2005-02-16 | Schering Plough Ltd | Compositions and method for treating infection in cattle and swine |
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 |
AU2005272925B2 (en) * | 2004-08-13 | 2011-02-10 | Intervet International B.V. | Pharmaceutical formulation comprising an antibiotic, a triazole and a corticosteroid |
EP1799636B1 (en) | 2004-09-23 | 2008-08-27 | Schering-Plough Ltd. | Control of parasites in animals by the use of novel trifluoromethanesulfonanilide oxime ether derivatives |
US7705038B2 (en) * | 2004-11-19 | 2010-04-27 | Intervet, Inc. | Control of parasites in animals by the use of parasiticidal 2-phenyl-3-(1H-pyrrol-2-yl)acrylonitrile derivatives |
PL1830885T3 (pl) * | 2004-12-21 | 2009-04-30 | Intervet Int Bv | Iniekcyjna kompozycja weterynaryjna zawierająca florfenikol |
CA2609574A1 (en) * | 2005-06-09 | 2006-12-21 | Schering-Plough Ltd. | Control of parasites in animals by n-[(phenyloxy)phenyl]-1,1,1-trifluoromethanesulfonamide and n-[(phenylsulfanyl)phenyl]-1,1,1-trifluoromethanesulfonamide derivatives |
TW200800924A (en) * | 2005-09-07 | 2008-01-01 | Schering Plough Ltd | A process for preparing oxazolidine protected aminodiol compounds useful as intermediates to florfenicol |
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 |
MX2009006467A (es) * | 2006-12-13 | 2009-08-21 | Schering Plough Ltd | Profarmacos solubles en agua de cloranfenicol, tiamfenicol y analogos de los mismos. |
WO2008076259A1 (en) * | 2006-12-13 | 2008-06-26 | Schering-Plough Ltd. | Water-soluble prodrugs of florfenicol and its analogs |
CA2685264A1 (en) * | 2007-04-27 | 2008-11-06 | Schering-Plough Ltd. | Compounds and methods for enhancing solubility of florfenicol and structurally-related antibiotics using cyclodextrins |
US20080319200A1 (en) * | 2007-05-30 | 2008-12-25 | Schering-Plough Animal Health Corp. | Process for preparing oxazoline-protected aminodiol compounds useful as intermediates to florfenicol |
TWI430995B (zh) | 2007-06-26 | 2014-03-21 | Du Pont | 萘異唑啉無脊椎有害動物控制劑 |
MX368680B (es) | 2007-06-27 | 2019-10-11 | Du Pont | Administración subcutánea de un derivado de isoxazol-benzamida para usarse en un método para proteger un mamífero de una pulga. |
JP2010534667A (ja) * | 2007-07-25 | 2010-11-11 | インターベツト・インターナシヨナル・ベー・ベー | オキサゾリジンおよびオキサゾリジノンアミノジオール類ならびに関連中間体を調製するためのプロセス |
US7550625B2 (en) * | 2007-10-19 | 2009-06-23 | Idexx Laboratories | Esters of florfenicol |
BRPI0818906A2 (pt) * | 2007-11-09 | 2015-05-12 | Intervet Int Bv | Formulação sólida de liberação rápida, preparação e uso da mesma |
TWI401023B (zh) | 2008-02-06 | 2013-07-11 | Du Pont | 中離子農藥 |
WO2010014566A2 (en) * | 2008-07-30 | 2010-02-04 | Intervet International B.V. | Process for preparing oxazoline-protected aminodiol compounds useful as intermediates to florfenicol |
JP2013501059A (ja) | 2009-08-05 | 2013-01-10 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | メソイオン性殺虫剤 |
UA110924C2 (uk) | 2009-08-05 | 2016-03-10 | Е. І. Дю Пон Де Немур Енд Компані | Мезоіонні пестициди |
UA107804C2 (en) | 2009-08-05 | 2015-02-25 | Du Pont | Mixtures of pesticides mezoionnyh |
MX2012001646A (es) | 2009-08-05 | 2012-03-21 | Du Pont | Pesticidas mesoionicos. |
BRPI1002023A2 (pt) | 2010-03-01 | 2011-10-25 | Nanocore Biotecnologia S A | forma farmacêutica sólida de dissolução rápida para tratamento de infecções bacterianas |
CA2799963C (en) | 2010-05-27 | 2018-01-23 | E. I. Du Pont De Nemours And Company | Crystalline form of 4- [5 - [3 -chloro-5 - (trifluoromethyl) phenyl] -4,5 -dihydro-5 - (trifluoromethyl) -3 - isoxazolyl] -n- [2-0x0-2- [(2,2,2-trifluoroethyl)amino]ethyl] -1-naphthalenecarboxamide |
WO2012087630A1 (en) | 2010-12-20 | 2012-06-28 | E.I. Du Pont De Nemours And Company | Pyridine and pyrimidine compounds for controlling invertebrate |
WO2013158422A1 (en) | 2012-04-17 | 2013-10-24 | E. I. Du Pont De Nemours And Company | Heterocyclic compounds for controlling invertebrate pests |
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 |
CN103254147B (zh) * | 2013-04-19 | 2016-04-06 | 浙江科技学院 | 一种d-苏式-2-(二氯甲基)-4,5-二氢-5-[对-(甲砜基)苯基]-4-噁唑甲醇的制备方法 |
CN106278964B (zh) * | 2016-07-31 | 2018-01-16 | 浙江润康药业有限公司 | 氟苯尼考的制备方法 |
CN106631872A (zh) * | 2016-12-13 | 2017-05-10 | 浙江普洛家园药业有限公司 | 一种氟苯尼考类似物中间体的合成方法 |
CN110272856B (zh) * | 2019-05-08 | 2022-05-03 | 江南大学 | 一种表达d-苏氨酸醛缩酶的重组菌及其构建方法与应用 |
CN117466787B (zh) * | 2023-12-28 | 2024-03-22 | 山东国邦药业有限公司 | 一种氟苯尼考中间体的制备方法 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2759001A (en) * | 1952-03-01 | 1956-08-14 | Parke Davis & Co | Process for the production of delta2-oxazolines |
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 |
EP0678506A3 (en) * | 1983-06-02 | 1996-07-24 | Zambon Spa | Intermediates for the preparation of 1-phenyl-1-hydroxy-2-amino-3-fluoropropane derivatives. |
US4876352A (en) * | 1988-09-14 | 1989-10-24 | Schering Corporation | Pressurized fluorination of hydroxy alkyl groups |
KR920701469A (ko) † | 1989-05-15 | 1992-08-11 | 스테이너 브이. 캔스태드 | 향균성 화합물 및 이의 중간물질의 제조방법 |
AU646910B2 (en) * | 1990-10-25 | 1994-03-10 | Schering Corporation | Process for preparing florfenicol, its analogs and oxazoline intermediates thereto |
-
1996
- 1996-08-19 US US08/699,271 patent/US5663361A/en not_active Expired - Lifetime
-
1997
- 1997-08-15 CO CO97047276A patent/CO4560550A1/es unknown
- 1997-08-15 AR ARP970103736A patent/AR008298A1/es not_active Application Discontinuation
- 1997-08-18 PL PL331644A patent/PL196454B1/pl not_active IP Right Cessation
- 1997-08-18 MY MYPI97003778A patent/MY115679A/en unknown
- 1997-08-18 PT PT97938263T patent/PT922040E/pt unknown
- 1997-08-18 HU HU9904166A patent/HU229610B1/hu unknown
- 1997-08-18 EP EP97938263.7A patent/EP0922040B2/en not_active Expired - Lifetime
- 1997-08-18 JP JP51080598A patent/JP3274868B2/ja not_active Expired - Lifetime
- 1997-08-18 BR BRPI9711318-2A patent/BR9711318B1/pt not_active IP Right Cessation
- 1997-08-18 IL IL12857497A patent/IL128574A/en not_active IP Right Cessation
- 1997-08-18 CN CN97198768A patent/CN1097583C/zh not_active Expired - Lifetime
- 1997-08-18 ZA ZA9707406A patent/ZA977406B/xx unknown
- 1997-08-18 PL PL378741A patent/PL198553B1/pl not_active IP Right Cessation
- 1997-08-18 CA CA002264116A patent/CA2264116C/en not_active Expired - Lifetime
- 1997-08-18 TR TR2008/00474T patent/TR200800474T2/xx unknown
- 1997-08-18 SK SK199-99A patent/SK286124B6/sk not_active IP Right Cessation
- 1997-08-18 PE PE1997000728A patent/PE99798A1/es not_active Application Discontinuation
- 1997-08-18 AU AU40638/97A patent/AU714495B2/en not_active Expired
- 1997-08-18 ES ES97938263T patent/ES2234026T5/es not_active Expired - Lifetime
- 1997-08-18 TR TR1999/00354T patent/TR199900354T2/xx unknown
- 1997-08-18 DK DK97938263T patent/DK0922040T3/da active
- 1997-08-18 NZ NZ334111A patent/NZ334111A/en not_active IP Right Cessation
- 1997-08-18 DE DE69731835T patent/DE69731835T3/de not_active Expired - Lifetime
- 1997-08-18 ID IDP972887A patent/ID18047A/id unknown
- 1997-08-18 CZ CZ0054099A patent/CZ297915B6/cs not_active IP Right Cessation
- 1997-08-18 AT AT97938263T patent/ATE283847T1/de active
- 1997-08-18 SI SI9730688T patent/SI0922040T1/xx unknown
- 1997-08-18 WO PCT/US1997/014205 patent/WO1998007709A1/en active Application Filing
- 1997-08-19 TW TW086111823A patent/TW381075B/zh not_active IP Right Cessation
-
1999
- 1999-02-18 NO NO19990756A patent/NO312962B1/no not_active IP Right Cessation
- 1999-02-18 KR KR1019997001290A patent/KR100286851B1/ko not_active IP Right Cessation
- 1999-07-10 HK HK99102946A patent/HK1017890A1/xx not_active IP Right Cessation
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