DK0555340T3 - Fremgangsmåde til fremstilling af florfenicol, analoger heraf og oxazolinmellemprodukter dertil - Google Patents
Fremgangsmåde til fremstilling af florfenicol, analoger heraf og oxazolinmellemprodukter dertilInfo
- Publication number
- DK0555340T3 DK0555340T3 DK91920162.4T DK91920162T DK0555340T3 DK 0555340 T3 DK0555340 T3 DK 0555340T3 DK 91920162 T DK91920162 T DK 91920162T DK 0555340 T3 DK0555340 T3 DK 0555340T3
- Authority
- DK
- Denmark
- Prior art keywords
- formula
- compound
- oxazoline
- oxazoline compound
- pct
- Prior art date
Links
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 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 1
- 229960003760 florfenicol Drugs 0.000 title 1
- 239000000543 intermediate Substances 0.000 title 1
- -1 oxazoline compound Chemical class 0.000 abstract 10
- 150000001875 compounds Chemical class 0.000 abstract 3
- 239000003153 chemical reaction reagent Substances 0.000 abstract 2
- 238000004519 manufacturing process Methods 0.000 abstract 2
- 239000012025 fluorinating agent Substances 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 238000001556 precipitation Methods 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
- 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
- C07D263/10—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Compounds Of Alkaline-Earth Elements, Aluminum Or Rare-Earth Metals (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Compounds Of Unknown Constitution (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60357590A | 1990-10-25 | 1990-10-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK0555340T3 true DK0555340T3 (da) | 1995-03-06 |
Family
ID=24416027
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK91920162.4T DK0555340T3 (da) | 1990-10-25 | 1991-10-23 | Fremgangsmåde til fremstilling af florfenicol, analoger heraf og oxazolinmellemprodukter dertil |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US5382673A (da) |
| EP (1) | EP0555340B1 (da) |
| JP (1) | JPH0645580B2 (da) |
| KR (1) | KR960008665B1 (da) |
| AT (1) | ATE115123T1 (da) |
| AU (1) | AU646910B2 (da) |
| CA (1) | CA2094810C (da) |
| CZ (1) | CZ286239B6 (da) |
| DE (1) | DE69105752T2 (da) |
| DK (1) | DK0555340T3 (da) |
| ES (1) | ES2067958T3 (da) |
| GR (1) | GR3015221T3 (da) |
| HK (1) | HK185496A (da) |
| HU (2) | HU9301182D0 (da) |
| NZ (2) | NZ250394A (da) |
| PL (1) | PL166385B1 (da) |
| RU (1) | RU2071468C1 (da) |
| SK (1) | SK281740B6 (da) |
| WO (1) | WO1992007824A1 (da) |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US5352832A (en) * | 1992-12-18 | 1994-10-04 | Schering Corporation | Asymmetric process for preparing florfenicol, thiamphenicol chloramphenicol and oxazoline intermediates |
| US5663361A (en) * | 1996-08-19 | 1997-09-02 | Schering Corporation | Process for preparing intermediates to florfenicol |
| CO5031296A1 (es) * | 1997-11-04 | 2001-04-27 | Novartis Ag | Derivados de azolina, compuestos que la contienen y metodo para la preparacion y aplicacion de dicho compuesto |
| US6348625B1 (en) * | 2000-11-10 | 2002-02-19 | Gloria Long Anderson | Method for preparing some 1-adamantancecarboxamides |
| NZ533242A (en) * | 2001-12-05 | 2007-11-30 | Duramed Pharmaceuticals Inc | Oral extended regime contraceptive package |
| 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 |
| 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. |
| CN1331849C (zh) * | 2005-08-12 | 2007-08-15 | 中国科学院上海有机化学研究所 | 甲砜霉素和氟苯尼考的新合成方法及其关键中间体 |
| 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 |
| EP2091909A1 (en) * | 2006-12-13 | 2009-08-26 | Schering-Plough Ltd. | Water-soluble prodrugs of florfenicol and its analogs |
| 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 |
| KR20100028537A (ko) * | 2007-04-27 | 2010-03-12 | 쉐링-프라우 리미티드 | 사이클로덱스트린을 사용하여 플로르페니콜 및 구조적으로 관련된 항생제의 용해도를 증진시키기 위한 화합물 및 방법 |
| 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 (da) | 2007-06-27 | 2018-02-05 | Du Pont | Fremgangsmåde til at kontrollere skadedyr hos dyr |
| 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 |
| 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 |
| CN105218474B (zh) * | 2015-10-22 | 2017-12-05 | 山东国邦药业股份有限公司 | (4r,5r)‑2‑二氯甲基‑4,5‑二氢‑5‑(4‑甲砜基苯基)‑4‑恶唑甲醇的合成方法 |
| 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 |
| CN109678811B (zh) * | 2019-01-25 | 2020-12-29 | 湖北中牧安达药业有限公司 | 一种氟苯尼考中间体环合物的不对称制备方法 |
| CN110330463B (zh) * | 2019-08-02 | 2021-05-14 | 山东国邦药业有限公司 | 一种氟苯尼考中间体的制备方法 |
| CN113264892B (zh) * | 2021-04-05 | 2022-12-20 | 复旦大学 | 一种使用微反应系统连续制备氟苯尼考关键中间体的方法 |
| 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 |
| CN113185474B (zh) * | 2021-07-02 | 2021-11-05 | 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 (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2686787A (en) * | 1954-08-17 | x xx xx - - | ||
| US2820041A (en) * | 1958-01-14 | Preparation of nitrophenyloxazolines | ||
| US2694071A (en) * | 1954-11-09 | Process for the preparation of tech | ||
| US2718520A (en) * | 1955-09-20 | Nitrophenyl-oxazolines and processes | ||
| US2402198A (en) * | 1944-09-06 | 1946-06-18 | Du Pont | Preparation of oxazolines |
| FR1071077A (fr) * | 1952-03-01 | 1954-08-24 | Parke Davis & Co | Procédé de production de delta 2-oxazolines |
| US2759001A (en) * | 1952-03-01 | 1956-08-14 | Parke Davis & Co | Process for the production of delta2-oxazolines |
| US2692897A (en) * | 1952-03-01 | 1954-10-26 | Parke Davis & Co | Process for the production of acylamido diol compounds |
| US2786870A (en) * | 1954-04-19 | 1957-03-26 | Parke Davis & Co | Synthesis of chloramphenicol and related acylamidodiols |
| DE2127776A1 (de) * | 1971-06-04 | 1972-12-14 | Chemische Werke Hüls AG, 4370 Mari | Verfahren zur Herstellung cyclischer Imidsäureester |
| HU167760B (da) * | 1972-10-20 | 1975-12-25 | ||
| DE2732213A1 (de) * | 1977-07-16 | 1979-01-25 | Bayer Ag | Derivate der cyclopropancarbonsaeurederivate, verfahren zu ihrer herstellung und ihre verwendung als zwischenprodukte zur herstellung von insektiziden |
| 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 |
| US5105009A (en) * | 1983-06-02 | 1992-04-14 | Zambon S.P.A. | Intermediates for the preparation of 1-(phenyl)-1-hydroxy-2-amino-3-fluoropropane derivatives |
| 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 |
| US5227494A (en) * | 1988-09-14 | 1993-07-13 | Schering Corporation | Process for preparing oxazoline compounds |
| JPH0670022B2 (ja) * | 1988-09-14 | 1994-09-07 | シェリング・コーポレーション | オキサゾリン化合物の製造方法 |
| 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). |
| US5243050A (en) * | 1990-12-20 | 1993-09-07 | North Carolina State University | Alkylpyridone DE ring intermediates useful for the manufacture of camptothecin and camptothecin analogs |
-
1991
- 1991-10-23 NZ NZ250394A patent/NZ250394A/en not_active IP Right Cessation
- 1991-10-23 CZ CZ1993710A patent/CZ286239B6/cs not_active IP Right Cessation
- 1991-10-23 NZ NZ240319A patent/NZ240319A/en not_active IP Right Cessation
- 1991-10-23 DE DE69105752T patent/DE69105752T2/de not_active Expired - Lifetime
- 1991-10-23 AT AT91920162T patent/ATE115123T1/de not_active IP Right Cessation
- 1991-10-23 AU AU89279/91A patent/AU646910B2/en not_active Expired
- 1991-10-23 US US08/039,450 patent/US5382673A/en not_active Expired - Lifetime
- 1991-10-23 PL PL91299059A patent/PL166385B1/pl unknown
- 1991-10-23 WO PCT/US1991/007608 patent/WO1992007824A1/en not_active Ceased
- 1991-10-23 DK DK91920162.4T patent/DK0555340T3/da active
- 1991-10-23 JP JP4500718A patent/JPH0645580B2/ja not_active Expired - Lifetime
- 1991-10-23 RU RU9193040370A patent/RU2071468C1/ru active
- 1991-10-23 HU HU931182A patent/HU9301182D0/hu unknown
- 1991-10-23 CA CA002094810A patent/CA2094810C/en not_active Expired - Lifetime
- 1991-10-23 SK SK377-93A patent/SK281740B6/sk not_active IP Right Cessation
- 1991-10-23 EP EP91920162A patent/EP0555340B1/en not_active Expired - Lifetime
- 1991-10-23 HU HU9301182A patent/HU212617B/hu unknown
- 1991-10-23 ES ES91920162T patent/ES2067958T3/es not_active Expired - Lifetime
-
1993
- 1993-04-24 KR KR93701226A patent/KR960008665B1/ko not_active Expired - Lifetime
-
1995
- 1995-02-28 GR GR950400425T patent/GR3015221T3/el unknown
-
1996
- 1996-10-03 HK HK185496A patent/HK185496A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ATE115123T1 (de) | 1994-12-15 |
| AU8927991A (en) | 1992-05-26 |
| PL166385B1 (en) | 1995-05-31 |
| HK185496A (en) | 1996-10-11 |
| DE69105752D1 (de) | 1995-01-19 |
| US5382673A (en) | 1995-01-17 |
| RU2071468C1 (ru) | 1997-01-10 |
| AU646910B2 (en) | 1994-03-10 |
| CZ286239B6 (cs) | 2000-02-16 |
| HU9301182D0 (en) | 1993-08-30 |
| NZ250394A (en) | 1994-10-26 |
| SK37793A3 (en) | 1993-10-06 |
| HU212617B (en) | 1996-09-30 |
| CA2094810A1 (en) | 1992-04-26 |
| NZ240319A (en) | 1994-10-26 |
| CA2094810C (en) | 2002-06-04 |
| EP0555340A1 (en) | 1993-08-18 |
| GR3015221T3 (en) | 1995-05-31 |
| JPH0645580B2 (ja) | 1994-06-15 |
| WO1992007824A1 (en) | 1992-05-14 |
| HUT65402A (en) | 1994-06-28 |
| SK281740B6 (sk) | 2001-07-10 |
| ES2067958T3 (es) | 1995-04-01 |
| CZ71093A3 (en) | 1994-02-16 |
| KR960008665B1 (en) | 1996-06-28 |
| DE69105752T2 (de) | 1995-05-11 |
| JPH05507289A (ja) | 1993-10-21 |
| EP0555340B1 (en) | 1994-12-07 |
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