NO303575B1 - Asymmetrisk fremgangsmate for fremstilling av florfenikol, tiamfenikol, kloramfenikol og oksazolinmellomprodukter - Google Patents

Asymmetrisk fremgangsmate for fremstilling av florfenikol, tiamfenikol, kloramfenikol og oksazolinmellomprodukter

Info

Publication number: NO303575B1
Authority: NO; Norway
Prior art keywords: acid; oxazoline; florfenicol; chloride; epoxide
Prior art date: 1992-12-18

Application number

NO19952425A

Other languages

English (en)

Norwegian (no)

Other versions

NO952425L (no

NO952425D0 (no

Inventor

Guang-Zhong Wu

Wanda I Tormos

Original Assignee

Schering Corp

Priority date (The priority date 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 date listed.)

1992-12-18

Filing date

1995-06-16

Publication date

1998-08-03

1995-06-16 Application filed by Schering Corp filed Critical Schering Corp

1995-06-16 Publication of NO952425L publication Critical patent/NO952425L/no

1995-06-16 Publication of NO952425D0 publication Critical patent/NO952425D0/no

1998-08-03 Publication of NO303575B1 publication Critical patent/NO303575B1/no

Links

IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 title abstract 5
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 4
229960003760 florfenicol Drugs 0.000 title abstract 4
238000000034 method Methods 0.000 title abstract 4
WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 title abstract 2
229960005091 chloramphenicol Drugs 0.000 title abstract 2
OTVAEFIXJLOWRX-NXEZZACHSA-N thiamphenicol Chemical compound CS(=O)(=O)C1=CC=C([C@@H](O)[C@@H](CO)NC(=O)C(Cl)Cl)C=C1 OTVAEFIXJLOWRX-NXEZZACHSA-N 0.000 title abstract 2
229960003053 thiamphenicol Drugs 0.000 title abstract 2
239000000543 intermediate Substances 0.000 title 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 4
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 abstract 4
239000002253 acid Substances 0.000 abstract 3
150000002118 epoxides Chemical class 0.000 abstract 3
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 2
150000008044 alkali metal hydroxides Chemical class 0.000 abstract 2
-1 alkylsulfonyl chloride Chemical compound 0.000 abstract 2
239000002585 base Substances 0.000 abstract 2
150000003512 tertiary amines Chemical class 0.000 abstract 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 abstract 2
STZZWJCGRKXEFF-UHFFFAOYSA-N Dichloroacetonitrile Chemical compound ClC(Cl)C#N STZZWJCGRKXEFF-UHFFFAOYSA-N 0.000 abstract 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 1
238000011914 asymmetric synthesis Methods 0.000 abstract 1
239000003054 catalyst Substances 0.000 abstract 1
239000003638 chemical reducing agent Substances 0.000 abstract 1
239000012320 chlorinating reagent Substances 0.000 abstract 1
238000006735 epoxidation reaction Methods 0.000 abstract 1
239000012025 fluorinating agent Substances 0.000 abstract 1
230000003301 hydrolyzing effect Effects 0.000 abstract 1
238000006317 isomerization reaction Methods 0.000 abstract 1
229910000104 sodium hydride Inorganic materials 0.000 abstract 1
239000012312 sodium hydride Substances 0.000 abstract 1
230000000707 stereoselective effect Effects 0.000 abstract 1
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 abstract 1
VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 abstract 1
WBYWAXJHAXSJNI-VOTSOKGWSA-N trans-cinnamic acid Chemical class OC(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-N 0.000 abstract 1
235000005074 zinc chloride Nutrition 0.000 abstract 1
239000011592 zinc chloride Substances 0.000 abstract 1

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)
Epoxy Compounds (AREA)

NO19952425A 1992-12-18 1995-06-16 Asymmetrisk fremgangsmate for fremstilling av florfenikol, tiamfenikol, kloramfenikol og oksazolinmellomprodukter NO303575B1 (no)

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 (3)

Publication Number	Publication Date
NO952425L NO952425L (no)	1995-06-16
NO952425D0 NO952425D0 (no)	1995-06-16
NO303575B1 true NO303575B1 (no)	1998-08-03

Family

ID=25540089

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19952425A NO303575B1 (no)	1992-12-18	1995-06-16	Asymmetrisk fremgangsmate for fremstilling av florfenikol, tiamfenikol, kloramfenikol og oksazolinmellomprodukter

Country Status (20)

Country	Link
US (1)	US5352832A (de)
EP (1)	EP0674618B1 (de)
JP (1)	JP3428016B2 (de)
KR (1)	KR100284216B1 (de)
AT (1)	ATE170835T1 (de)
AU (1)	AU676003B2 (de)
CA (1)	CA2152089C (de)
CZ (1)	CZ287461B6 (de)
DE (1)	DE69320986T2 (de)
DK (1)	DK0674618T3 (de)
ES (1)	ES2120605T3 (de)
FI (1)	FI109295B (de)
HU (1)	HU225110B1 (de)
NO (1)	NO303575B1 (de)
NZ (1)	NZ259239A (de)
PL (1)	PL177891B1 (de)
RU (1)	RU2126383C1 (de)
SK (1)	SK281701B6 (de)
UA (1)	UA43331C2 (de)
WO (1)	WO1994014764A1 (de)

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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
CA2550660C (en) *	2003-12-23	2011-03-15	Schering-Plough Ltd.	Florfenicol prodrug having improved water solubility
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
KR101289115B1 (ko) *	2004-08-13	2013-07-23	엠에스디 인터내셔널 홀딩즈 게엠베하	항생제인 트리아졸 및 코르티코스테로이드를 포함하는약제학적 제형
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
EP1811841B1 (de) *	2004-11-19	2009-10-28	Schering-Plough Ltd.	Kontrolle von parasiten bei tieren mittels verwendung von parasitiziden 2-phenyl-3-(1h-pyrrol-2-yl) acrylonitril-derivaten
PL1830885T3 (pl) *	2004-12-21	2009-04-30	Intervet Int Bv	Iniekcyjna kompozycja weterynaryjna zawierająca florfenikol
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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
WO2008076259A1 (en) *	2006-12-13	2008-06-26	Schering-Plough Ltd.	Water-soluble prodrugs of florfenicol and its analogs
CA2672795A1 (en) *	2006-12-13	2008-06-26	Schering-Plough Ltd.	Water-soluble prodrugs of chloramphenicol, thiamphenicol, and analogs thereof
MX2009011642A (es) *	2007-04-27	2010-01-29	Schering Plough Ltd	Compuestos y metodos para potenciar la solubilidad de florfenicol y antibioticos estructuralmente relacionados utilizando ciclodextrinas.
TWI430995B (zh)	2007-06-26	2014-03-21	Du Pont	萘異唑啉無脊椎有害動物控制劑
KR101769728B1 (ko)	2007-06-27	2017-08-18	이 아이 듀폰 디 네모아 앤드 캄파니	동물 해충 방제 방법
US7550625B2 (en) *	2007-10-19	2009-06-23	Idexx Laboratories	Esters of florfenicol
NZ585219A (en)	2007-11-09	2012-11-30	Intervet Int Bv	Fast release solid formulation, preparation and use thereof
TWI468407B (zh)	2008-02-06	2015-01-11	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
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
US20120122680A1 (en)	2009-08-05	2012-05-17	E.I. Du Pont De Nemours And Company	Mesoionic pesticides
UA110924C2 (uk)	2009-08-05	2016-03-10	Е. І. Дю Пон Де Немур Енд Компані	Мезоіонні пестициди
UA107804C2 (xx)	2009-08-05	2015-02-25	Du Pont	Суміші мезоіонних пестицидів
KR20120050467A (ko)	2009-08-05	2012-05-18	이 아이 듀폰 디 네모아 앤드 캄파니	메소이온성 살충제
BRPI1002023A2 (pt)	2010-03-01	2011-10-25	Nanocore Biotecnologia S A	forma farmacêutica sólida de dissolução rápida para tratamento de infecções bacterianas
UA108881C2 (xx)	2010-05-27	2015-06-25		Кристалічна форма 4-$5-$3-хлор-5-(трифторметил)феніл]-4,5-дигідро-5-(трифторметил)-3-ізоксазоліл]-n-$2-оксо-2-$(2,2,2-трифторетил)аміно]етил]-1-нафталінкарбоксаміду
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
WO2012105574A1 (ja) *	2011-01-31	2012-08-09	国立大学法人長崎大学	光学活性化合物又はその塩の製造方法
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
WO2015157927A1 (zh) *	2014-04-16	2015-10-22	湖北美天生物科技有限公司	氟苯尼考的合成方法
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
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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1992
- 1992-12-18 US US07/993,932 patent/US5352832A/en not_active Expired - Lifetime
1993
- 1993-12-15 AT AT94903599T patent/ATE170835T1/de active
- 1993-12-15 ES ES94903599T patent/ES2120605T3/es not_active Expired - Lifetime
- 1993-12-15 HU HU9501776A patent/HU225110B1/hu unknown
- 1993-12-15 UA UA95073385A patent/UA43331C2/uk unknown
- 1993-12-15 EP EP94903599A patent/EP0674618B1/de not_active Expired - Lifetime
- 1993-12-15 WO PCT/US1993/012071 patent/WO1994014764A1/en not_active Ceased
- 1993-12-15 DE DE69320986T patent/DE69320986T2/de not_active Expired - Lifetime
- 1993-12-15 SK SK777-95A patent/SK281701B6/sk not_active IP Right Cessation
- 1993-12-15 CZ CZ19951598A patent/CZ287461B6/cs not_active IP Right Cessation
- 1993-12-15 KR KR1019950702466A patent/KR100284216B1/ko not_active Expired - Lifetime
- 1993-12-15 AU AU57484/94A patent/AU676003B2/en not_active Expired
- 1993-12-15 PL PL93309393A patent/PL177891B1/pl unknown
- 1993-12-15 NZ NZ259239A patent/NZ259239A/en not_active IP Right Cessation
- 1993-12-15 RU RU95115555A patent/RU2126383C1/ru active
- 1993-12-15 JP JP51523294A patent/JP3428016B2/ja not_active Expired - Lifetime
- 1993-12-15 CA CA002152089A patent/CA2152089C/en not_active Expired - Lifetime
- 1993-12-15 DK DK94903599T patent/DK0674618T3/da 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
FI109295B (fi)	2002-06-28
DK0674618T3 (da)	1999-02-22
HU225110B1 (en)	2006-06-28
JP3428016B2 (ja)	2003-07-22
JPH08504819A (ja)	1996-05-28
CA2152089C (en)	2006-10-24
ES2120605T3 (es)	1998-11-01
AU676003B2 (en)	1997-02-27
CA2152089A1 (en)	1994-07-07
HU9501776D0 (en)	1995-08-28
KR100284216B1 (ko)	2001-04-02
CZ287461B6 (en)	2000-11-15
PL177891B1 (pl)	2000-01-31
ATE170835T1 (de)	1998-09-15
EP0674618A1 (de)	1995-10-04
SK281701B6 (sk)	2001-07-10
CZ159895A3 (en)	1996-01-17
WO1994014764A1 (en)	1994-07-07
DE69320986D1 (de)	1998-10-15
US5352832A (en)	1994-10-04
DE69320986T2 (de)	1999-03-04
AU5748494A (en)	1994-07-19
FI952872L (fi)	1995-06-12
PL309393A1 (en)	1995-10-02
NO952425L (no)	1995-06-16
KR950704244A (ko)	1995-11-17
FI952872A0 (fi)	1995-06-12
UA43331C2 (uk)	2001-12-17
EP0674618B1 (de)	1998-09-09
SK77795A3 (en)	1995-12-06
HUT72669A (en)	1996-05-28
NZ259239A (en)	1996-04-26
RU2126383C1 (ru)	1999-02-20
NO952425D0 (no)	1995-06-16

Legal Events

Date

Code

Title

Description

2012-09-24

CHAD

Change of the owner's name or address (par. 44 patent law, par. patentforskriften)

Owner name: MERCK SHARP AND DOHME CORP

Free format text: NEW ADDRESS: 126 EAST LINCOLN AVENUE, US-NJ07065 RAHWAY, US

2014-01-13

MK1K

Patent expired

Publication	Publication Date	Title
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