PE20091088A1 - PROCESS FOR THE PREPARATION OF MEDETOMIDINE - Google Patents
PROCESS FOR THE PREPARATION OF MEDETOMIDINEInfo
- 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
Links
- HRLIOXLXPOHXTA-UHFFFAOYSA-N medetomidine Chemical compound C=1C=CC(C)=C(C)C=1C(C)C1=CN=C[N]1 HRLIOXLXPOHXTA-UHFFFAOYSA-N 0.000 title abstract 2
- 229960002140 medetomidine Drugs 0.000 title abstract 2
- -1 2,3-DIMETHYLBENZYL HALIDE Chemical class 0.000 abstract 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- FGLBSLMDCBOPQK-UHFFFAOYSA-N 2-nitropropane Chemical compound CC(C)[N+]([O-])=O FGLBSLMDCBOPQK-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 abstract 1
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 Table
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (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
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)
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 |
CN102753532B (en) * | 2009-12-09 | 2015-05-13 | I-技术有限公司 | Process for preparation of medetomidine |
WO2013014428A1 (en) * | 2011-07-22 | 2013-01-31 | Cambrex Karlskoga Ab | New processes for preparing 4-substituted imidazoles |
SG11201405611SA (en) | 2012-05-08 | 2014-11-27 | Lonza Ag | Method for preparation of 2-(2,3-dimethylphenyl)-1-propanal |
EA025950B1 (en) * | 2012-05-08 | 2017-02-28 | Лонца Лтд. | Method for preparation of medetomidine |
WO2012172119A2 (en) * | 2012-05-08 | 2012-12-20 | Lonza Ltd | Method for the preparation of medetomidine |
AU2012285678B2 (en) | 2012-06-28 | 2016-02-25 | Lonza Ltd | Method for preparation of 2-(2,3-dimethylphenyl)-1-propanal with chloroacetone |
JP5777841B2 (en) * | 2012-06-28 | 2015-09-09 | ロンザ・リミテッド | Process for the preparation of medetomidine using 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 |
CN117295718A (en) | 2022-03-22 | 2023-12-26 | 维科-兹多洛夫希沃特尼赫有限责任公司 | Method for preparing medetomidine and derivative thereof |
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)
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 |
-
2007
- 2007-10-24 GB GB0720891A patent/GB2453982B/en not_active Expired - Fee Related
-
2008
- 2008-10-22 UY UY31415A patent/UY31415A1/en not_active Application Discontinuation
- 2008-10-22 AR ARP080104589A patent/AR068952A1/en unknown
- 2008-10-23 PE PE2008001820A patent/PE20091088A1/en not_active Application Discontinuation
- 2008-10-24 WO PCT/GB2008/003613 patent/WO2009053709A1/en active Application Filing
- 2008-10-24 CL CL2008003185A patent/CL2008003185A1/en unknown
Also Published As
Publication number | Publication date |
---|---|
WO2009053709A1 (en) | 2009-04-30 |
CL2008003185A1 (en) | 2009-03-06 |
AR068952A1 (en) | 2009-12-16 |
GB2453982B (en) | 2009-09-16 |
UY31415A1 (en) | 2009-05-29 |
GB2453982A (en) | 2009-04-29 |
GB0720891D0 (en) | 2007-12-05 |
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Legal Events
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FA | Abandonment or withdrawal |