WO2014026657A3 - A process for the preparation of a derivative of 2-methyl-2'-phenylpropionic acid using new intermediates - Google Patents

A process for the preparation of a derivative of 2-methyl-2'-phenylpropionic acid using new intermediates Download PDF

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Publication number
WO2014026657A3
WO2014026657A3 PCT/CZ2013/000092 CZ2013000092W WO2014026657A3 WO 2014026657 A3 WO2014026657 A3 WO 2014026657A3 CZ 2013000092 W CZ2013000092 W CZ 2013000092W WO 2014026657 A3 WO2014026657 A3 WO 2014026657A3
Authority
WO
WIPO (PCT)
Prior art keywords
methyl
preparation
formula
phenylpropionic acid
derivative
Prior art date
Application number
PCT/CZ2013/000092
Other languages
French (fr)
Other versions
WO2014026657A2 (en
Inventor
Josef Zezula
Josef Hajicek
Original Assignee
Zentiva, K.S
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 Zentiva, K.S filed Critical Zentiva, K.S
Publication of WO2014026657A2 publication Critical patent/WO2014026657A2/en
Publication of WO2014026657A3 publication Critical patent/WO2014026657A3/en

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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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4

Abstract

The present invention deals with a preparation method of derivatives of methyl-2 '- phenylpropionic acid, e.g. the antihistamine bilastine of formula 9 that uses a new intermediate of formula 27 in the form of a base or salt. The intermediate reacts with a suitable alkylation reagent and with the use of auxiliary reagents, producing the ester of formula 16, wherein R stands for a C 1-C4 alkyl, which is subsequently alkali or acid hydrolyzed to bilastine. Formula 9, 27, 16
PCT/CZ2013/000092 2012-08-15 2013-08-06 A process for the preparation of a derivative of 2-methyl-2'-phenylpropionic acid using new intermediates WO2014026657A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CZ2012-551A CZ307500B6 (en) 2012-08-15 2012-08-15 A method of the preparation of a 2-methyl-2'-phenylpropionic acid derivative employing novel intermediates
CZPV2012-551 2012-08-15

Publications (2)

Publication Number Publication Date
WO2014026657A2 WO2014026657A2 (en) 2014-02-20
WO2014026657A3 true WO2014026657A3 (en) 2014-04-10

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CZ2013/000092 WO2014026657A2 (en) 2012-08-15 2013-08-06 A process for the preparation of a derivative of 2-methyl-2'-phenylpropionic acid using new intermediates

Country Status (2)

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CZ (1) CZ307500B6 (en)
WO (1) WO2014026657A2 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106349214A (en) * 2015-07-13 2017-01-25 南京长澳医药科技有限公司 Method for preparing bilastine impurity

Families Citing this family (15)

* Cited by examiner, † Cited by third party
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CN105017211A (en) * 2014-04-30 2015-11-04 重庆华邦制药有限公司 2-phenyl propionic ester derivative and preparation method and application thereof
CN104151290A (en) * 2014-06-30 2014-11-19 北京万全德众医药生物技术有限公司 Method for preparing novel crystal form of bilastine
CN104177331B (en) * 2014-09-10 2016-08-17 北京科莱博医药开发有限责任公司 The preparation method of bilastine
CN104326909A (en) * 2014-09-22 2015-02-04 暨南大学 Methods for preparation of alpha, alpha-dimethyl-4-(2-haloethyl) phenyl acetate and synthesis of bilastine
ES2600827B9 (en) * 2015-07-24 2018-03-28 Urquima, S.A CRYSTALLINE FORMS OF BILASTINE AND PROCEDURES FOR PREPARATION
CN105254579A (en) * 2015-09-19 2016-01-20 万全万特制药江苏有限公司 Method for preparing bilastine intermediate through one-kettle process
WO2017167949A1 (en) 2016-04-01 2017-10-05 Krka, D.D., Novo Mesto Crystalline forms of bilastine
WO2017191651A1 (en) * 2016-05-05 2017-11-09 Msn Laboratories Private Limited, R & D Center Solid state forms of 2-[4-(2-{4-[1-(2-ethoxyethyl)-1h-benzimidazol-2-yl]-1-piperidinyl}ethyl)phenyl]-2-methylpropanoic acid and process for preparation thereof
CN106146459B (en) * 2016-07-18 2019-12-20 山东罗欣药业集团恒欣药业有限公司 Preparation method of bilastine
CN109212116B (en) * 2017-07-04 2023-10-03 万全万特制药江苏有限公司 Method for separating and measuring chemical purity of bilastine intermediate by high performance liquid chromatography
ES2813561T3 (en) 2017-09-07 2021-03-24 Tiefenbacher Alfred E Gmbh & Co Kg Pharmaceutical composition in tablet comprising bilastine
ES2835287T3 (en) 2017-12-18 2021-06-22 Tiefenbacher Alfred E Gmbh & Co Kg Pharmaceutical tablet composition comprising polymorphic form 3 of bilastine and magnesium aluminometasilicate
ES2864176T3 (en) 2017-12-18 2021-10-13 Tiefenbacher Alfred E Gmbh & Co Kg Pharmaceutical tablet composition comprising bilastine form 3 and a water soluble filler
CN110105204A (en) * 2019-06-04 2019-08-09 荆楚理工学院 A kind of 4- (the halogenated isobutyryl of 2-) benzyl carbinol derivative and preparation method thereof
CN113292534B (en) * 2021-05-27 2022-04-26 常州大学 Preparation method of bilastine key intermediate

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EP0818454A1 (en) * 1996-06-04 1998-01-14 Fabrica Espanola De Productos Quimicos Y Farmaceuticos, S.A. (Faes) Benzimidazole derivatives with antihistaminic activity
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AP9801283A0 (en) * 1996-01-03 1998-09-30 Smithkline Beecham Plc Carbamoyloxy derivatives of mutiline and their use as antibacterials.
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EP0818454A1 (en) * 1996-06-04 1998-01-14 Fabrica Espanola De Productos Quimicos Y Farmaceuticos, S.A. (Faes) Benzimidazole derivatives with antihistaminic activity
WO2009102155A2 (en) * 2008-02-12 2009-08-20 Yuhan Corporation Process for preparation of 2-methyl-2´-phenylpropionic acid derivatives and novel intermediate compounds

Non-Patent Citations (4)

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Title
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MORTEN JØRGENSEN ET AL: "Efficient Synthesis of [alpha]-Aryl Esters by Room-Temperature Palladium-Catalyzed Coupling of Aryl Halides with Ester Enolates", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 124, no. 42, 1 October 2002 (2002-10-01), pages 12557 - 12565, XP055087738, ISSN: 0002-7863, DOI: 10.1021/ja027643u *
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106349214A (en) * 2015-07-13 2017-01-25 南京长澳医药科技有限公司 Method for preparing bilastine impurity
CN106349214B (en) * 2015-07-13 2020-11-03 南京长澳医药科技有限公司 Preparation method of bilastine impurity

Also Published As

Publication number Publication date
CZ307500B6 (en) 2018-10-24
CZ2012551A3 (en) 2014-02-26
WO2014026657A2 (en) 2014-02-20

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