PE20091088A1 - PROCESS FOR THE PREPARATION OF MEDETOMIDINE - Google Patents

PROCESS FOR THE PREPARATION OF MEDETOMIDINE

Info

Publication number
PE20091088A1
PE20091088A1 PE2008001820A PE2008001820A PE20091088A1 PE 20091088 A1 PE20091088 A1 PE 20091088A1 PE 2008001820 A PE2008001820 A PE 2008001820A PE 2008001820 A PE2008001820 A PE 2008001820A PE 20091088 A1 PE20091088 A1 PE 20091088A1
Authority
PE
Peru
Prior art keywords
dimethylbenzyl
aldehyde
dimethyl
reacting
temperature equal
Prior art date
Application number
PE2008001820A
Other languages
Spanish (es)
Inventor
Rasik Somaiya
Jonathan Cranke
Kristian Bragg
Muhammad Raza
Original Assignee
Norbrook Lab 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 Norbrook Lab Ltd filed Critical Norbrook Lab Ltd
Publication of PE20091088A1 publication Critical patent/PE20091088A1/en

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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/20—Hypnotics; Sedatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives
    • 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
    • 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
    • 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
    • C07D233/64—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 substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Pain & Pain Management (AREA)
  • Anesthesiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

REFERIDA UN PROCEDIMIENTO PARA PREPARAR MEDETOMIDINA QUE COMPRENDE: A) REACCIONAR UN HALURO DE 2,3-DIMETILBENCILO CON ETOXIDO DE SODIO Y 2-NITROPROPANO A UNA TEMPERATURA IGUAL O INFERIOR A 50 °C PARA FORMAR ALDEHIDO DE 2,3-DIMETILBENCILO; B) AGREGAR ALDEHIDO DE 2,3-DIMETILBENCILO A UNA SOLUCION DE HALURO DE METILMAGNESIO PARA FORMAR ALCOHOL 2,3-DIMETIL-METILBENCILICO; Y C) REACCIONAR EL ALCOHOL 2,3-DIMETIL-METILBENCILICO CON N-TRIMETILSILILIMIDAZOL EN PRESENCIA DE CLORURO DE TITANIO (IV) EN CLORURO DE METILENO ANHIDRO A UNA TEMPERATURA IGUAL O INFERIOR A 45 °C. DICHO PROCESO ES INDUSTRIALMENTE INOCUO Y FACIL DE MANIPULAR A TEMPERATURAS RELATIVAMENTE MODERADASREFERRED TO A PROCEDURE FOR PREPARING MEDETOMIDINE, INCLUDING: A) REACTING A 2,3-DIMETHYLBENZYL HALIDE WITH SODIUM ETOXIDE AND 2-NITROPROPANE AT A TEMPERATURE EQUAL TO OR LESS THAN 50 ° C TO FORM 2,3-DIMETHYLBENZYL ALDEHYDE; B) ADDING 2,3-DIMETHYLBENZYL ALDEHYDE TO A METHYLMAGNESIUM HALIDE SOLUTION TO FORM 2,3-DIMETHYL-METHYLBENZYL ALCOHOL; AND C) REACTING 2,3-DIMETHYL-METHYLBENZYL ALCOHOL WITH N-TRIMETHYLSILILIMIDAZOLE IN THE PRESENCE OF TITANIUM (IV) CHLORIDE IN ANHYDROUS METHYLENE CHLORIDE AT A TEMPERATURE EQUAL TO OR LOWER THAN 45 ° C. SAID PROCESS IS INDUSTRIALLY SAFE AND EASY TO HANDLE AT RELATIVELY MODERATE TEMPERATURES

PE2008001820A 2007-10-24 2008-10-23 PROCESS FOR THE PREPARATION OF MEDETOMIDINE PE20091088A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB0720891A GB2453982B (en) 2007-10-24 2007-10-24 Chemical process for the preparation of Medetomidine

Publications (1)

Publication Number Publication Date
PE20091088A1 true PE20091088A1 (en) 2009-07-20

Family

ID=38829878

Family Applications (1)

Application Number Title Priority Date Filing Date
PE2008001820A PE20091088A1 (en) 2007-10-24 2008-10-23 PROCESS FOR THE PREPARATION OF MEDETOMIDINE

Country Status (6)

Country Link
AR (1) AR068952A1 (en)
CL (1) CL2008003185A1 (en)
GB (1) GB2453982B (en)
PE (1) PE20091088A1 (en)
UY (1) UY31415A1 (en)
WO (1) WO2009053709A1 (en)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101921234B (en) * 2009-06-12 2012-05-30 中国中化股份有限公司 Method for preparing dexmedetomidine
WO2011070069A1 (en) 2009-12-09 2011-06-16 I-Tech Ab Process for preparation of medetomidine
DK2734508T3 (en) 2011-07-22 2018-05-22 Cambrex Karlskoga Ab NEW PROCEDURES FOR THE PREPARATION OF 4-SUBSTITUTED IMIDAZOLS
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
WO2012172119A2 (en) * 2012-05-08 2012-12-20 Lonza Ltd Method for the preparation of medetomidine
CA2866437C (en) 2012-06-28 2018-01-02 Lonza Ltd. Method for preparation of medetomidine with chloroacetone
BR112014022268A8 (en) 2012-06-28 2019-05-28 Lonza Ag Method for preparing 2- (2,3-dimethylphenyl) -1-propanal with chloroacetone
CN106588777A (en) * 2015-10-16 2017-04-26 江苏开元医药化工有限公司 Industrial preparation method of dexmedetomidine hydrochloride
WO2023182903A1 (en) 2022-03-22 2023-09-28 Общество с ограниченной ответственностью "ВИК-здоровье животных" Method for producing medetomidine and its derivatives
CN114671811A (en) * 2022-04-14 2022-06-28 南京正科医药股份有限公司 Racemization recovery method of dexmedetomidine resolution byproduct

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2101114B (en) * 1981-07-10 1985-05-22 Farmos Group Ltd Substituted imidazole derivatives and their preparation and use

Also Published As

Publication number Publication date
UY31415A1 (en) 2009-05-29
CL2008003185A1 (en) 2009-03-06
WO2009053709A1 (en) 2009-04-30
AR068952A1 (en) 2009-12-16
GB2453982A (en) 2009-04-29
GB0720891D0 (en) 2007-12-05
GB2453982B (en) 2009-09-16

Similar Documents

Publication Publication Date Title
PE20091088A1 (en) PROCESS FOR THE PREPARATION OF MEDETOMIDINE
BR112014003198A2 (en) compounds for the treatment and prophylaxis of respiratory syncytial virus disease
AR087794A1 (en) PROCESS TO PREPARE {1- {1- [3-FLUORO-2- (TRIFLUOROMETIL) ISONICOTINOIL] -PIPERIDIN-4-IL} -3- [4- (7H-PIRROLO [2,3-D] PIRIMIDIN-4-IL ) -1H-PIRAZOL-1-IL] AZETIDIN-3-IL} ACETONITRILE, INTERMEDIARIES OF SUCH SYNTHESIS AND PROCESS TO PREPARE THEM
PE20142294A1 (en) INDOLE AND INDAZOLE COMPOUNDS THAT ACTIVATE AMPK
BR112014011055A2 (en) new [1,2,3] triazolo [4,5-d] pyrimidine derivatives
BR112015031079A2 (en) aminotriazine derivatives and pharmaceutical composition containing said aminotriazine derivatives
BR112014012479A2 (en) [1,2,3] triazole [4,5-d] pyrimidine derivatives as cannabinoid receptor 2 agonist agonists
BR112014006217A2 (en) use of acylsulfonamides to improve plant yield
BRPI0911035A2 (en) pyrrolidinone glycokase activators
BR112012013847A2 (en) new indolinone cyclopropane derivatives
ECSP109938A (en) NEW CRYSTAL FORM OF 3- (DIFLUOROMETIL) -1-METIL-N- (3 ', 4', 5'-TRIFLUORO [1,1'-BIFENIL] -2-IL) -1H-PIRAZOL-4-CARBOXAMIDA
BR112012019011A2 (en) "process for making titanium zeolite- mww".
AR081819A1 (en) DERIVATIVES OF PIRIMIDIL-PIPERIDINIL-OXIPIRIDINONA, PHARMACEUTICAL COMPOSITIONS THAT CONTAIN THEM AND USE OF THE SAME TO TREAT DIABETES, DYSLIPEMIAS, OBESITY AND OTHER DISEASES
AR082776A1 (en) STABILIZATION OF STIMULATING FOLICLE HORMONE (FSH)
AR063747A1 (en) DEFINILAZETIDINONE REPLACED WITH PIPERAZINE-1-SULPHONIC ACID AND THAT HAS IMPROVED PHARMACOLOGICAL PROPERTIES
PH12014502453B1 (en) Process for preparation of optically pure and optionally substituted 2-(1-hydroxy-alkyl)- chromen-4-one derivatives and their use in preparing pharmaceuticals
AR092960A1 (en) PROCEDURE TO PREPARE TIENOPIRIMIDINE COMPOUNDS
BR112012017994B8 (en) liquid composition, use of a liquid composition, and, methods for preparing a liquid composition and for treating a disorder
CL2009000682A1 (en) Non-hygroscopic salt, free of hydrogen chloride for food products, with the formula mgkx (nh4) yclgzh2o; particle, composition, aqueous solution, nutritive substance, flavoring and processed product comprising the salt; method of reducing the sodium content of a food; and salt preparation methods.
BR112015029714A2 (en) process for preparing 4,6-bis (aryloxy) pyrimidine derivatives
CL2011002045A1 (en) Compound derived from n - [(3e) -5- (cycloalkylamino) -5-oxo-1-phenylpent-3-en-2-yl] benzamide, useful in the treatment of pruritus of unknown cause or associated with a dermatological disease such such as atopic dermatitis, psoriasis, urticaria, among others; pharmaceutical combination.
BR112012033599A2 (en) new tetrahydroquinoline derivatives.
AR081514A1 (en) COMPOUND 4- [ETHYL (DIMETHYL) AMMONIUM] BUTANOATE, THE METHOD FOR THE PREPARATION OF THE SAME AND THE USE IN THE TREATMENT OF CARDIOVASCULAR DISEASE
BR112013009043B8 (en) compound, pharmaceutical composition, and use of a compound
CL2012000270A1 (en) Preparation procedure of ivabradine and its addition salts by formation of the benzoacepine ring; and the intermediary compounds considered in the process.

Legal Events

Date Code Title Description
FA Abandonment or withdrawal