WO2006006184A3 - Procede de production de loratadine et ses intermediaires - Google Patents

Procede de production de loratadine et ses intermediaires Download PDF

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Publication number
WO2006006184A3
WO2006006184A3 PCT/IN2005/000235 IN2005000235W WO2006006184A3 WO 2006006184 A3 WO2006006184 A3 WO 2006006184A3 IN 2005000235 W IN2005000235 W IN 2005000235W WO 2006006184 A3 WO2006006184 A3 WO 2006006184A3
Authority
WO
WIPO (PCT)
Prior art keywords
produce
ketone
loratadine
acid
followed
Prior art date
Application number
PCT/IN2005/000235
Other languages
English (en)
Other versions
WO2006006184A2 (fr
Inventor
Sanjay Suri
Tapan Kashyap
Krishan Singh Verma
Netar Singh
Original Assignee
Morepen Lab Ltd
Sanjay Suri
Tapan Kashyap
Krishan Singh Verma
Netar Singh
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 Morepen Lab Ltd, Sanjay Suri, Tapan Kashyap, Krishan Singh Verma, Netar Singh filed Critical Morepen Lab Ltd
Publication of WO2006006184A2 publication Critical patent/WO2006006184A2/fr
Publication of WO2006006184A3 publication Critical patent/WO2006006184A3/fr

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Classifications

    • 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
    • C07D401/02—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 two hetero rings
    • C07D401/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond

Abstract

L'invention concerne un procédé consistant: i) à soumettre un halide de benzyle substitué à une cyanuration dans un système biphase à l'aide de solvants non miscibles dans l'eau au moyen de procédés quelconques connus; ii) à condenser in situ le phényle acétonitrile ainsi obtenu à l'aide d'un ester nicotinique en présence d'un alkoxyde de métal alcalin et d'un solvant organique non miscible dans l'eau afin de produire un cétonitrile; iii) à hydrolyser puis à décarboxyler ledit cétonitrile in situ en cétone respective dans un environnement acide en-dessous de 60° C; iv) à soumettre la cétone ainsi obtenue à une réduction suivie d'une N-oxydation, d'une cyanuration et d'une hydrolyse au moyen de procédés quelconques connus afin de produire un acide picolinique; v) à cycliser l'acide picolinique en cétone tricyclique au moyen de procédés classiques; vi) à traiter la cétone tricyclique à l'aide d'un composé organométallique contenant Mg afin de produire un carbinol; viii) à purifier le carbinol à l'aide d'un agent de purification sélectionné à partir d'un solvant organique polaire miscible dans l'eau, puis à le déshydrater à l'aide d'un acide sulfurique à une température inférieure à 50° C afin d'obtenir un produit N-méthyle (oléfine) et à soumettre cette oléfine à une N-carbéthoxylation afin de produire une loratadine. Ladite loratadine peut également être préparée par traitement d'un composé cayano à l'aide du composé organométallique contenant Mg afin de produire une cétone au moyen des procédés connus de l'état de la technique suivi d'une cyclisation en présence d'un mélange d'acide sulfurique et d'une source d'acide borique afin d'obtenir un produit N-méthyle et de le convertir en loratadine par N-carbéthoxylation.
PCT/IN2005/000235 2004-07-08 2005-07-06 Procede de production de loratadine et ses intermediaires WO2006006184A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN1271DE2004 2004-07-08
IN1271/DEL/2004 2004-07-08

Publications (2)

Publication Number Publication Date
WO2006006184A2 WO2006006184A2 (fr) 2006-01-19
WO2006006184A3 true WO2006006184A3 (fr) 2006-10-26

Family

ID=35457853

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2005/000235 WO2006006184A2 (fr) 2004-07-08 2005-07-06 Procede de production de loratadine et ses intermediaires

Country Status (1)

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WO (1) WO2006006184A2 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102336739B (zh) * 2011-07-15 2012-09-26 海南灵康制药有限公司 一种氯雷他定化合物及其制法
CN112341433A (zh) * 2020-11-16 2021-02-09 成都大学 一种氯雷他定的制备方法
CN113135893B (zh) * 2021-06-21 2022-02-11 北京鑫开元医药科技有限公司 苯并环庚烷并吡啶化合物、其制备方法及其用途
CN113135899B (zh) * 2021-06-21 2021-11-23 北京鑫开元医药科技有限公司 苯并环庚烷并吡啶化合物、其制备方法及其用途
CN114085209B (zh) * 2022-01-10 2022-06-03 北京鑫开元医药科技有限公司 一种氯雷他定关键中间体的纯化方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3717647A (en) * 1971-04-09 1973-02-20 Schering Corp Alpha-nicotinoyl phenylacetonitriles
US4659716A (en) * 1984-02-15 1987-04-21 Schering Corporation Antihistaminic 8-(halo)-substituted 6,11-dihydro-11-(4-piperidylidene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridines

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3717647A (en) * 1971-04-09 1973-02-20 Schering Corp Alpha-nicotinoyl phenylacetonitriles
US4659716A (en) * 1984-02-15 1987-04-21 Schering Corporation Antihistaminic 8-(halo)-substituted 6,11-dihydro-11-(4-piperidylidene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridines

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
PIWINSKI J J ET AL: "Dual antagonists of platelet activating factor and histamine.Identification of structural requirements for dual activity of N-acyl-4-(5,6-dihydro-11H-benzo[5,6]cyclohepta-[1,2-b]pyridin-11-y lidene)piperidines", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY. WASHINGTON, US, vol. 34, no. 1, 1991, pages 457 - 461, XP002169640, ISSN: 0022-2623 *

Also Published As

Publication number Publication date
WO2006006184A2 (fr) 2006-01-19

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