WO2012172119A3 - Procédé de préparation de médétomidine - Google Patents

Procédé de préparation de médétomidine Download PDF

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Publication number
WO2012172119A3
WO2012172119A3 PCT/EP2012/070870 EP2012070870W WO2012172119A3 WO 2012172119 A3 WO2012172119 A3 WO 2012172119A3 EP 2012070870 W EP2012070870 W EP 2012070870W WO 2012172119 A3 WO2012172119 A3 WO 2012172119A3
Authority
WO
WIPO (PCT)
Prior art keywords
preparation
medetomidine
aceton
dimethylbenzene
bromo
Prior art date
Application number
PCT/EP2012/070870
Other languages
English (en)
Other versions
WO2012172119A2 (fr
Inventor
Florencio Zaragoza Doerwald
Anna KULESZA
Stephan Elzner
Robert BUJOK
Zbigniew WROBEL
Krzysztof Wojciechowski
Original Assignee
Lonza Ltd
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.)
Filing date
Publication date
Application filed by Lonza Ltd filed Critical Lonza Ltd
Priority to NZ700640A priority Critical patent/NZ700640B2/en
Priority to PCT/EP2012/072796 priority patent/WO2013011155A2/fr
Priority to HUE12784296A priority patent/HUE027384T2/en
Priority to US14/386,054 priority patent/US9045433B2/en
Priority to ES12784296.1T priority patent/ES2563816T3/es
Priority to AU2012285675A priority patent/AU2012285675B2/en
Priority to CA2866424A priority patent/CA2866424A1/fr
Priority to KR1020147029915A priority patent/KR101530506B1/ko
Priority to JP2015510660A priority patent/JP5779297B2/ja
Priority to IN7983DEN2014 priority patent/IN2014DN07983A/en
Priority to DK12784296.1T priority patent/DK2847173T3/en
Priority to MYPI2014002563A priority patent/MY166058A/en
Priority to PL12784296T priority patent/PL2847173T3/pl
Priority to EA201400940A priority patent/EA025950B1/ru
Priority to CN201280072266.6A priority patent/CN104245679B/zh
Priority to EP12784296.1A priority patent/EP2847173B1/fr
Priority to SG11201405606RA priority patent/SG11201405606RA/en
Publication of WO2012172119A2 publication Critical patent/WO2012172119A2/fr
Publication of WO2012172119A3 publication Critical patent/WO2012172119A3/fr
Priority to TW102116032A priority patent/TWI529164B/zh
Priority to CL2014002905A priority patent/CL2014002905A1/es
Priority to HK15102124.8A priority patent/HK1201532A1/zh
Priority to HRP20160215T priority patent/HRP20160215T1/hr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C07D233/58—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
    • C07C1/24—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by elimination of water
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
    • C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
    • C07C29/40—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing carbon-to-metal bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/18—Monohydroxylic alcohols containing only six-membered aromatic rings as cyclic part
    • C07C33/20—Monohydroxylic alcohols containing only six-membered aromatic rings as cyclic part monocyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
    • C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
    • C07C45/58—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in three-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/228—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings, e.g. phenylacetaldehyde
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • C07C2531/025—Sulfonic acids

Abstract

L'invention concerne un procédé de préparation de médétomidine à partir de 1-bromo 2,3-diméthylbenzène et d'acétone.
PCT/EP2012/070870 2012-05-08 2012-10-22 Procédé de préparation de médétomidine WO2012172119A2 (fr)

Priority Applications (21)

Application Number Priority Date Filing Date Title
MYPI2014002563A MY166058A (en) 2012-05-08 2012-11-15 Method for preparation of medetomidine
SG11201405606RA SG11201405606RA (en) 2012-05-08 2012-11-15 Method for preparation of medetomidine
DK12784296.1T DK2847173T3 (en) 2012-05-08 2012-11-15 METHOD OF PRODUCING Medetomidine
US14/386,054 US9045433B2 (en) 2012-05-08 2012-11-15 Method for preparation of medetomidine
ES12784296.1T ES2563816T3 (es) 2012-05-08 2012-11-15 Método de preparación de medetomidina
AU2012285675A AU2012285675B2 (en) 2012-05-08 2012-11-15 Method for preparation of medetomidine
CA2866424A CA2866424A1 (fr) 2012-05-08 2012-11-15 Procede de preparation de medetomidine
KR1020147029915A KR101530506B1 (ko) 2012-05-08 2012-11-15 메데토미딘 제조 방법
JP2015510660A JP5779297B2 (ja) 2012-05-08 2012-11-15 メデトミジンの調製のための方法
PL12784296T PL2847173T3 (pl) 2012-05-08 2012-11-15 Sposób wytwarzania medetomidyny
HUE12784296A HUE027384T2 (en) 2012-05-08 2012-11-15 A method for preparing medetomidine
NZ700640A NZ700640B2 (en) 2012-05-08 2012-11-15 Method for preparation of medetomidine
IN7983DEN2014 IN2014DN07983A (fr) 2012-05-08 2012-11-15
EA201400940A EA025950B1 (ru) 2012-05-08 2012-11-15 Способ получения медетомидина
CN201280072266.6A CN104245679B (zh) 2012-05-08 2012-11-15 美托咪定的制备方法
EP12784296.1A EP2847173B1 (fr) 2012-05-08 2012-11-15 Procédé de préparation de médétomidine
PCT/EP2012/072796 WO2013011155A2 (fr) 2012-05-08 2012-11-15 Procédé de préparation de médétomidine
TW102116032A TWI529164B (zh) 2012-05-08 2013-05-06 製備美托咪啶之方法
CL2014002905A CL2014002905A1 (es) 2012-05-08 2014-10-27 Un metodo para la preparacion de medetomidina a partir de 1-bromo-2,3-dimetilbenceno y acetona, util como agente sedante y analgesico veterinario.
HK15102124.8A HK1201532A1 (zh) 2012-05-08 2015-03-03 美托咪定的製備方法
HRP20160215T HRP20160215T1 (hr) 2012-05-08 2016-03-01 Postupak za pripravu medetomidina

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US201261644284P 2012-05-08 2012-05-08
EP12167134.1 2012-05-08
US61/644,284 2012-05-08
EP12167134 2012-05-08

Publications (2)

Publication Number Publication Date
WO2012172119A2 WO2012172119A2 (fr) 2012-12-20
WO2012172119A3 true WO2012172119A3 (fr) 2013-04-04

Family

ID=47357537

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2012/070870 WO2012172119A2 (fr) 2012-05-08 2012-10-22 Procédé de préparation de médétomidine

Country Status (2)

Country Link
UA (1) UA112344C2 (fr)
WO (1) WO2012172119A2 (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2012285676B2 (en) * 2012-05-08 2016-02-25 Lonza Ltd Method for preparation of 2-(2,3-dimethylphenyl)-1-propanal
US9045433B2 (en) * 2012-05-08 2015-06-02 Lonza Ltd. Method for preparation of medetomidine
CA2866437C (fr) * 2012-06-28 2018-01-02 Lonza Ltd. Procede de preparation de medetomidine a partir de chloro-acetone
BR112014022268A8 (pt) * 2012-06-28 2019-05-28 Lonza Ag método para preparação de 2-(2,3-dimetilfenil)-1-propanal com cloroacetona
JP6799603B2 (ja) 2016-09-14 2020-12-16 株式会社スクウェア・エニックス 映像表示システム及び映像表示方法、映像表示プログラム
CN111903674B (zh) * 2020-08-05 2022-07-12 马保臣 一种质量均一稳定的过硫酸氢钾复合粉及其制备工艺
CN117384006B (zh) * 2023-12-08 2024-04-19 寿光市诚信盐业有限公司 一种溴苯的制备方法

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2252080A1 (de) * 1971-10-28 1973-05-03 Sandoz Ag Verfahren zur herstellung neuer carbocyclischer verbindungen
EP0058047A1 (fr) * 1981-02-05 1982-08-18 Farmos-Yhtyma Oy Dérivés d'imidazoles substitués, leur préparation et leur utilisation
GB2101114A (en) * 1981-07-10 1983-01-12 Farmos Group Ltd Substituted imidazole derivatives and their preparation and use
GB2453982A (en) * 2007-10-24 2009-04-29 Norbrook Lab Ltd Chemical process for the preparation of Medetomidine
WO2009089132A1 (fr) * 2008-01-09 2009-07-16 Allergan, Inc. Composés substitués d'aryl-2-phényléthyl-1h-imidazole, modulateurs sélectifs du sous-type des récepteurs adrénergiques alpha 2b et/ou alpha 2c
WO2012172120A2 (fr) * 2012-05-08 2012-12-20 Lonza Ltd 2-(2,3-diméthylphényl)-1-propanal et son utilisation comme parfum

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE513474C2 (sv) 1999-01-25 2000-09-18 Hans Elwing Instutionen Foer C Metod för att förhindra kräftdjurs, särskilt havstulpaners, etablering på fasta ytor med hjälp av en substans som stör nervsignaler, varvid substansen är medetomidin, dvs (+)-4-/1- (2,3-dimetylfenyl)-etyl/-IH-imidazol
EP1918282A1 (fr) 2006-11-06 2008-05-07 "Joint Stock Company Grindeks" Procédé pour la préparation de medetomidine et ses sels

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2252080A1 (de) * 1971-10-28 1973-05-03 Sandoz Ag Verfahren zur herstellung neuer carbocyclischer verbindungen
EP0058047A1 (fr) * 1981-02-05 1982-08-18 Farmos-Yhtyma Oy Dérivés d'imidazoles substitués, leur préparation et leur utilisation
GB2101114A (en) * 1981-07-10 1983-01-12 Farmos Group Ltd Substituted imidazole derivatives and their preparation and use
GB2453982A (en) * 2007-10-24 2009-04-29 Norbrook Lab Ltd Chemical process for the preparation of Medetomidine
WO2009089132A1 (fr) * 2008-01-09 2009-07-16 Allergan, Inc. Composés substitués d'aryl-2-phényléthyl-1h-imidazole, modulateurs sélectifs du sous-type des récepteurs adrénergiques alpha 2b et/ou alpha 2c
WO2012172120A2 (fr) * 2012-05-08 2012-12-20 Lonza Ltd 2-(2,3-diméthylphényl)-1-propanal et son utilisation comme parfum

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
CHARLES F HUEBNER ET AL: "THE ACONITE ALKAtOIDS XVI. ON STAPHISINE AND THE HYDROCARBON OBTAINED FROM ITS DEHYDROGENATION", JOURNAL OF BIOLOGICAL CHEMISTRY, AMERICAN SOCIETY FOR BIOCHEMISTRY AND MOLECULAR BIOLOGY, US, vol. 169, 1947, pages 211 - 220, XP008157366, ISSN: 0021-9258 *
CORDI A A ET AL: "EFFICIENT SYNTHESIS OF (S)-4(5)-Ä1-(2,3-DIMETHYLPHENYL)ETHYLÜIMIDAZOLE TARTRATE, THE POTENT ALPHA2 ADRENOCEPTOR AGONIST DEXMEDETOMIDINE", SYNTHETIC COMMUNICATIONS: AN INTERNATIONAL JOURNAL FOR RAPID COMMUNICATION OF SYNTHETIC ORGANIC CHEMISTRY, TAYLOR & FRANCIS INC, PHILADELPHIA, PA; US, vol. 26, no. 8, 1996, pages 1585 - 1593, XP009014489, ISSN: 0039-7911, DOI: 10.1080/00397919608003527 *
MUKHERJEE-MÜLLER ET AL: "176. Säurekatalysierte Umlagerungen von 1,5.Dimethyl-6-methyliden-tricyclo[3.2.1.0 2,7]oct-3-en-8endo-olen", HELVETICA CHIMICA ACTA,, vol. 60, no. 5, 1977, pages 1758 - 1780, XP002683671 *
ZHAO-RONG ZHANG ET AL: "ULTRASOUND-PROMOTED SYNTHESIS OF SUBSTITUTED PHENANTHRENE-1,4- QUINONES; THE STRUCTURE OF PLECTRANTHON D", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM, NL, vol. 35, no. 14, 4 April 1994 (1994-04-04), pages 2153 - 2156, XP000434277, ISSN: 0040-4039, DOI: 10.1016/S0040-4039(00)76783-9 *

Also Published As

Publication number Publication date
WO2012172119A2 (fr) 2012-12-20
UA112344C2 (uk) 2016-08-25

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