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WO2006114676A3 - A process for the preparation of rupatadine - Google Patents

A process for the preparation of rupatadine Download PDF

Info

Publication number
WO2006114676A3
WO2006114676A3 PCT/IB2006/000964 IB2006000964W WO2006114676A3 WO 2006114676 A3 WO2006114676 A3 WO 2006114676A3 IB 2006000964 W IB2006000964 W IB 2006000964W WO 2006114676 A3 WO2006114676 A3 WO 2006114676A3
Authority
WO
WIPO (PCT)
Prior art keywords
rupatadine
solvent
desloratadine
reaction
preparation
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/IB2006/000964
Other languages
French (fr)
Other versions
WO2006114676A8 (en
WO2006114676A2 (en
Inventor
Khamar Bakulesh Mafatlal
Modi Indravadan Ambalal
Shukla Manish Chandrakant
Parikh Krunal Kashyapbhai
Dange Suryabhan Prabhakar
Ponniah Ravi
Desai Sanjay Jagdish
J Venkat Raman
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Individual
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of WO2006114676A2 publication Critical patent/WO2006114676A2/en
Publication of WO2006114676A3 publication Critical patent/WO2006114676A3/en
Anticipated expiration legal-status Critical
Publication of WO2006114676A8 publication Critical patent/WO2006114676A8/en
Ceased legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyridine Compounds (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

Rupatadine is synthesized by phase transfer catalysed N-alkylation of Desloratadine in biphasic solvent system using aqueous alkali by reaction of a compound of formula (A), X= leaving group as -OH -OTs, OMs -OAc -OAr -Br -Cl, -l with Desloratadine at temperature up to 50°C , wherein solvent selected is water immiscible organic solvent. Rupatadine is further converted to Rupatadine fumarate by reaction of Rupatadine in ketonic solvent with an alcoholic solution of fumaric acid.
PCT/IB2006/000964 2005-04-27 2006-04-22 A process for the preparation of rupatadine Ceased WO2006114676A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN516/MUM/2005 2005-04-27
IN516MU2005 2005-04-27

Publications (3)

Publication Number Publication Date
WO2006114676A2 WO2006114676A2 (en) 2006-11-02
WO2006114676A3 true WO2006114676A3 (en) 2007-01-25
WO2006114676A8 WO2006114676A8 (en) 2007-11-22

Family

ID=37215116

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2006/000964 Ceased WO2006114676A2 (en) 2005-04-27 2006-04-22 A process for the preparation of rupatadine

Country Status (2)

Country Link
ES (1) ES2311426B1 (en)
WO (1) WO2006114676A2 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10463656B2 (en) 2017-01-05 2019-11-05 Iowa State University Research Foundation, Inc. Methods and compositions for prevention of feedlot bovine respiratory disease

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101531654B (en) * 2009-04-13 2013-07-17 浙江赐富医药有限公司 Preparation method for Rupatadine
CN102043025B (en) * 2009-10-22 2014-04-16 北京万全阳光医学技术有限公司 Method for measuring materials associated with rupatadine intermediate by high performance liquid chromatography
JP5978296B2 (en) * 2011-06-28 2016-08-24 フジアン・ミンドン・レジュヴネイション・ファーマスーティカル・カンパニー・リミテッド Anti-allergic benzocycloheptathiophene derivatives
CN102680622A (en) * 2011-12-17 2012-09-19 东莞达信生物技术有限公司 A kind of liquid chromatography detection method of rupatadine fumarate content
CN103304542B (en) * 2013-06-21 2014-07-23 四川海思科制药有限公司 Rupatadine fumarate compound
EP2824103B1 (en) 2013-07-09 2016-04-27 Cadila Pharmaceuticals Limited An improved process for the preparation of Rupatadine Fumarate
CN104163786B (en) * 2014-06-10 2016-08-24 上海应用技术学院 A kind of method preparing 5-methyl-3-bromo methyl cycloheptapyridine hydrobromate
CN109456143A (en) * 2018-11-27 2019-03-12 郑州师范学院 The purification process of tetrachloro-ethylene
CN114133353B (en) * 2021-12-10 2023-12-01 重庆华邦制药有限公司 Rupatadine fumarate intermediate and preparation method of rupatadine fumarate
CN114920727B (en) * 2022-05-26 2023-07-25 重庆华邦制药有限公司 Preparation method of rupatadine

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5407941A (en) * 1992-05-22 1995-04-18 J. Uriach & Cia. S.A. 8-chloro-11-[1-[(5-methyl-3-pyridyl)methyl]-4-piperidyliden]-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,]pyridine

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2087818B1 (en) * 1993-11-24 1997-03-16 Uriach & Cia Sa J 8-CHLORINE-11- (1 - ((5-METHYL-3-PIRIDYL) METHYL) -4-PIPERIDYLIDEN) -6,11-DIHYDRO-5H-BENZO- (5,6) CYCLOHEPTAL (1,2-B) PIRIDINE, SMOKING.
WO2004080945A1 (en) * 2003-03-12 2004-09-23 Natco Pharma Limited Process for the preparation of n-methyl-1-naphthalenemethanamine

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5407941A (en) * 1992-05-22 1995-04-18 J. Uriach & Cia. S.A. 8-chloro-11-[1-[(5-methyl-3-pyridyl)methyl]-4-piperidyliden]-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,]pyridine

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CARCELLER E. ET AL.: "[(3-Pyridylalkyl)piperidylidene]benzocyclohepatypyridine derivatives as Dual Antagonists of PAF and Histamine", J. MED. CHEM., vol. 37, 1994, pages 2697 - 2703, XP003005099 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10463656B2 (en) 2017-01-05 2019-11-05 Iowa State University Research Foundation, Inc. Methods and compositions for prevention of feedlot bovine respiratory disease

Also Published As

Publication number Publication date
ES2311426B1 (en) 2009-12-22
ES2311426A1 (en) 2009-02-01
WO2006114676A8 (en) 2007-11-22
WO2006114676A2 (en) 2006-11-02

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