PE99798A1 - Proceso para preparar intermediarios de florfenicol - Google Patents
Proceso para preparar intermediarios de florfenicolInfo
- Publication number
- PE99798A1 PE99798A1 PE1997000728A PE00072897A PE99798A1 PE 99798 A1 PE99798 A1 PE 99798A1 PE 1997000728 A PE1997000728 A PE 1997000728A PE 00072897 A PE00072897 A PE 00072897A PE 99798 A1 PE99798 A1 PE 99798A1
- Authority
- PE
- Peru
- Prior art keywords
- compound
- formula
- alkyl
- iii
- reaction container
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 3
- AYIRNRDRBQJXIF-NXEZZACHSA-N (-)-Florfenicol Chemical compound CS(=O)(=O)C1=CC=C([C@@H](O)[C@@H](CF)NC(=O)C(Cl)Cl)C=C1 AYIRNRDRBQJXIF-NXEZZACHSA-N 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 6
- QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 abstract 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 abstract 1
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical group C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- ZJULYDCRWUEPTK-UHFFFAOYSA-N dichloromethyl Chemical compound Cl[CH]Cl ZJULYDCRWUEPTK-UHFFFAOYSA-N 0.000 abstract 1
- 229960003760 florfenicol Drugs 0.000 abstract 1
- 208000015181 infectious disease Diseases 0.000 abstract 1
- 244000005700 microbiome Species 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- 239000011591 potassium Substances 0.000 abstract 1
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
SE REFIERE AL PROCEDIMIENTO DE PREPARACION DEL COMPUESTO (I), QUE COMPRENDE: (1) CONTACTAR UN COMPUESTO DE FORMULA (II) CON UN AGENTE REDUCTOR COMO BOROHIDRURO DE POTASIO, EN UN RECIPIENTE DE REACCION ADECUADO, PARA OBTENER UN COMPUESTO (III); (2) HACER REACCIONAR EN EL MISMO RECIPIENTE DE REACCION, UN COMPUESTO DE FORMULA (III) CON R"-CN. ESTE PROCESO ELIMINA AISLAR EL COMPUESTO (III), YA QUE AMBOS PASOS (1) Y (2), SON LLEVADOS A CABO EN EL MISMO RECIPIENTE. LOS COMPUESTOS OBTENIDOS DE FORMULA (I), EN DONDE LA CONFIGURACION DEL ANILLO OXAZOLIDINA ES 4R TRANS; R ES H, NO2, CH3S, CH3SO2 o ALQUILO C4-C6; R" ES ARILO, HALOARILO, BENCILO, BENCILO SUSTITUIDO, ALQUILO C1-C6, HALOALQUILO, CICLOALQUILO C3-C7, DE PREFERENCIA R ES SO2CH3 Y R" ES FENILO o CHCl2, SON COMPUESTOS INTERMEDIOS EN EL PROCESO DE OBTENCION DEL [R-(R*,S*)]-2,2-DICLORO-N-[1-(FLUOROMETIL)-2-HIDROXI-2-[4-(METILSULFONIL)FENIL]ETIL]ACETAMIDA, CONOCIDO COMO FLORFENICOL, EL CUAL ES UN AGENTE ANTIBACTERIANO DE AMPLIO ESPECTRO EN EL TRATAMIENTO DE INFECCIONES CAUSADAS POR MICROORGANISMOS GRAM POSITIVOS, 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 |
|---|---|
| PE99798A1 true PE99798A1 (es) | 1998-12-28 |
Family
ID=24808601
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PE1997000728A PE99798A1 (es) | 1996-08-19 | 1997-08-18 | Proceso para preparar intermediarios de florfenicol |
Country Status (30)
| 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) |
| 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 |
| CN1649829A (zh) * | 2002-03-08 | 2005-08-03 | 先灵-普劳有限公司 | 新型氟苯尼考类抗生素 |
| MY146351A (en) | 2003-05-29 | 2012-08-15 | Schering Plough Ltd | Compositions 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 |
| PE20060489A1 (es) | 2004-08-13 | 2006-06-19 | Schering Plough Ltd | Formulacion farmaceutica que comprende un antibiotico, un triazol y un corticosteroide |
| ATE406348T1 (de) | 2004-09-23 | 2008-09-15 | Schering Plough Ltd | Bekämpfung von parasiten in tieren durch verwendung neuer trifluormethansulfonanilidoximetherderivate |
| MX2007006072A (es) * | 2004-11-19 | 2007-07-11 | Schering Plough Ltd | Control de parasitos en animales mediante el uso de derivados del parasiticida 2-fenil-3-(1h-pirrol-2-il)acrilonitrilo. |
| ES2315942T3 (es) * | 2004-12-21 | 2009-04-01 | Intervet International Bv | Composicion veterinaria inyectable que contiene florfenicol. |
| MX2007015729A (es) * | 2005-06-09 | 2008-02-21 | 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. |
| AU2006287696A1 (en) | 2005-09-07 | 2007-03-15 | Schering-Plough Pty. Limited | 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 |
| CN101600686A (zh) * | 2006-12-13 | 2009-12-09 | 先灵-普劳有限公司 | 氯霉素、甲砜霉素及其类似物的水溶性前药 |
| EP2091909A1 (en) * | 2006-12-13 | 2009-08-26 | Schering-Plough Ltd. | Water-soluble prodrugs of florfenicol and its analogs |
| KR20100028537A (ko) * | 2007-04-27 | 2010-03-12 | 쉐링-프라우 리미티드 | 사이클로덱스트린을 사용하여 플로르페니콜 및 구조적으로 관련된 항생제의 용해도를 증진시키기 위한 화합물 및 방법 |
| CA2688432A1 (en) * | 2007-05-30 | 2008-12-11 | Schering-Plough Ltd. | A 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 |
| DK2957284T3 (en) | 2007-06-27 | 2018-02-05 | Du Pont | PROCEDURE TO CHECK ANIMALS FOR ANIMALS |
| WO2009015111A2 (en) * | 2007-07-25 | 2009-01-29 | Intervet Intermatonal B.V. | Process for preparing oxazolidine-and oxazolidinone-aminodiols and related intermediates |
| US7550625B2 (en) * | 2007-10-19 | 2009-06-23 | Idexx Laboratories | Esters of florfenicol |
| MX2010005087A (es) * | 2007-11-09 | 2010-05-21 | Intervet Int Bv | Formulacion solida de liberacion rapida, preparacion y uso de la misma. |
| TWI401023B (zh) | 2008-02-06 | 2013-07-11 | Du Pont | 中離子農藥 |
| JP2011529895A (ja) * | 2008-07-30 | 2011-12-15 | インターベツト・インターナシヨナル・ベー・ベー | フロルフェニコール中間体として有用なオキサゾリン保護アミノジオール化合物を調製する方法 |
| MX2012001651A (es) | 2009-08-05 | 2012-03-16 | Du Pont | Pesticidas mesoionicos. |
| UA107804C2 (en) | 2009-08-05 | 2015-02-25 | Du Pont | Mixtures of pesticides mezoionnyh |
| UA110924C2 (uk) | 2009-08-05 | 2016-03-10 | Е. І. Дю Пон Де Немур Енд Компані | Мезоіонні пестициди |
| US20120122680A1 (en) | 2009-08-05 | 2012-05-17 | 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 |
| MX2012013758A (es) | 2010-05-27 | 2013-01-24 | Du Pont | Forma cristalina de 4-[5-[3-cloro-5-trifluorometil)fenil]-4,5-dihi dro-5-(trifluorometil)-3-isoxazolil]-n-[2-oxo-2-[(2,2,2-trifluoro etil)amino]etil]-1-naftalenocarboxamida. |
| 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 |
| EP0130633B1 (en) * | 1983-06-02 | 1996-10-09 | ZAMBON GROUP S.p.A. | Process for the preparation of 1-(phenyl)-1-hydroxy-2-amino-3-fluoro propane 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 |
| NZ250394A (en) * | 1990-10-25 | 1994-10-26 | Schering Corp | Fluorinated and hydroxylated oxazoline compounds |
-
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 SK SK199-99A patent/SK286124B6/sk not_active IP Right Cessation
- 1997-08-18 ID IDP972887A patent/ID18047A/id unknown
- 1997-08-18 BR BRPI9711318-2A patent/BR9711318B1/pt not_active IP Right Cessation
- 1997-08-18 WO PCT/US1997/014205 patent/WO1998007709A1/en not_active Ceased
- 1997-08-18 PT PT97938263T patent/PT922040E/pt unknown
- 1997-08-18 NZ NZ334111A patent/NZ334111A/en not_active IP Right Cessation
- 1997-08-18 ZA ZA9707406A patent/ZA977406B/xx unknown
- 1997-08-18 AU AU40638/97A patent/AU714495B2/en not_active Expired
- 1997-08-18 MY MYPI97003778A patent/MY115679A/en unknown
- 1997-08-18 CN CN97198768A patent/CN1097583C/zh not_active Expired - Lifetime
- 1997-08-18 TR TR2008/00474T patent/TR200800474T2/xx unknown
- 1997-08-18 CZ CZ0054099A patent/CZ297915B6/cs not_active IP Right Cessation
- 1997-08-18 CA CA002264116A patent/CA2264116C/en not_active Expired - Lifetime
- 1997-08-18 DE DE69731835T patent/DE69731835T3/de not_active Expired - Lifetime
- 1997-08-18 AT AT97938263T patent/ATE283847T1/de active
- 1997-08-18 PL PL331644A patent/PL196454B1/pl not_active IP Right Cessation
- 1997-08-18 PE PE1997000728A patent/PE99798A1/es not_active Application Discontinuation
- 1997-08-18 TR TR1999/00354T patent/TR199900354T2/xx unknown
- 1997-08-18 HU HU9904166A patent/HU229610B1/hu unknown
- 1997-08-18 JP JP51080598A patent/JP3274868B2/ja not_active Expired - Lifetime
- 1997-08-18 SI SI9730688T patent/SI0922040T1/xx unknown
- 1997-08-18 IL IL12857497A patent/IL128574A/en not_active IP Right Cessation
- 1997-08-18 DK DK97938263T patent/DK0922040T3/da active
- 1997-08-18 ES ES97938263T patent/ES2234026T5/es not_active Expired - Lifetime
- 1997-08-18 PL PL378741A patent/PL198553B1/pl not_active IP Right Cessation
- 1997-08-18 EP EP97938263.7A patent/EP0922040B2/en not_active Expired - Lifetime
- 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 Expired - Lifetime
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG | Grant, registration | ||
| FD | Application declared void or lapsed |