MX348635B - Proceso para preparación de derivados de ácido pirazol carboxílico. - Google Patents

Proceso para preparación de derivados de ácido pirazol carboxílico.

Info

Publication number
MX348635B
MX348635B MX2015001023A MX2015001023A MX348635B MX 348635 B MX348635 B MX 348635B MX 2015001023 A MX2015001023 A MX 2015001023A MX 2015001023 A MX2015001023 A MX 2015001023A MX 348635 B MX348635 B MX 348635B
Authority
MX
Mexico
Prior art keywords
isomer
carboxylic acid
pyrazole carboxylic
undesired
preparation
Prior art date
Application number
MX2015001023A
Other languages
English (en)
Other versions
MX2015001023A (es
Inventor
Groebke Zbinden Katrin
Koerner Matthias
Bartels Bjoern
Bliss Fritz
Original Assignee
Hoffmann La Roche
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 Hoffmann La Roche filed Critical Hoffmann La Roche
Publication of MX2015001023A publication Critical patent/MX2015001023A/es
Publication of MX348635B publication Critical patent/MX348635B/es

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
    • C07C227/16—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions not involving the amino or carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C269/04—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups from amines with formation of carbamate groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/12—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
    • C07C281/02—Compounds containing any of the groups, e.g. carbazates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
    • C07C281/02—Compounds containing any of the groups, e.g. carbazates
    • C07C281/04—Compounds containing any of the groups, e.g. carbazates the other nitrogen atom being further doubly-bound to a carbon atom
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Abstract

La presente invención se refiere a un nuevo proceso para la preparación de un derivado de ácido pirazol carboxílico de la fórmula (I) en donde R1 es alquilo-C1-7 y R3 es alquilo-C1-7 que está opcionalmente sustituido con halógeno o alcoxi-C1-4. El derivado de ácido pirazol carboxílico de la fórmula I se puede utilizar como bloque de construcción en la preparación de principios farmacéuticamente activos, por ejemplo, para compuestos que actúan como inhibidores de fosfodiesterasa (PDE), particularmente inhibidores de PDE10. Los inhibidores de PDE10 tienen el potencial para tratar trastornos psicóticos como esquizofrenia (Publicación de patente Int. WC 2011/117264). Un enfoque sintético para el derivado de ácido pirazol carboxílico de la fórmula I se ha descrito en el esquema de reacción 3 de la publicación de patente Int. WC 2011/117264 aplicando un método descrito en Hanzlowsky et al, J. Heterocyclic Chem. 2003, 40 (3), 487-489. Sin embargo, bajo condiciones de ciclocondensación catalizadas por ácido descritas, además del isómero deseado, también se formó una cantidad sustancial del isómero sustituido N-1 no deseado. En muchos casos, especialmente en mayor escala, este isómero no deseado es el producto principal en la mezcla de reacción con proporciones de hasta 70:30 en favor del isómero no deseado, conduciendo a rendimientos aislados de aproximadamente 30% del isómero no deseado, junto con aproximadamente 25% del isómero deseado.
MX2015001023A 2012-08-17 2013-08-14 Proceso para preparación de derivados de ácido pirazol carboxílico. MX348635B (es)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP12180802 2012-08-17
PCT/EP2013/066953 WO2014027009A1 (en) 2012-08-17 2013-08-14 Process for the preparation of pyrazole carboxylic acid derivatives

Publications (2)

Publication Number Publication Date
MX2015001023A MX2015001023A (es) 2015-04-08
MX348635B true MX348635B (es) 2017-06-22

Family

ID=46851296

Family Applications (1)

Application Number Title Priority Date Filing Date
MX2015001023A MX348635B (es) 2012-08-17 2013-08-14 Proceso para preparación de derivados de ácido pirazol carboxílico.

Country Status (12)

Country Link
US (1) US9346763B2 (es)
EP (1) EP2885276B1 (es)
JP (1) JP6122118B2 (es)
KR (1) KR20150042847A (es)
CN (1) CN104540807B (es)
BR (1) BR112015002779A2 (es)
CA (1) CA2880846A1 (es)
ES (1) ES2588056T3 (es)
HK (1) HK1206358A1 (es)
MX (1) MX348635B (es)
RU (1) RU2638112C2 (es)
WO (1) WO2014027009A1 (es)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111617342B (zh) 2014-04-25 2022-08-16 拜耳医药保健有限公司 具有滚动膜片的注射器
ES2566228B1 (es) * 2014-09-11 2017-02-08 Consejo Superior De Investigaciones Cientificas Uso de ésteres derivados de pirazol protón-ionizables y sus correspondientes sales para el tratamiento de la enfermedad de Chagas y la leishmaniasis
CN104529899A (zh) * 2014-12-19 2015-04-22 浙江泰达作物科技有限公司 高区域选择性制备1-烷基-3-卤代烷基吡唑衍生物的方法
TWI621454B (zh) 2015-04-24 2018-04-21 拜耳保健公司 帶有滾動膜片的注射器
WO2018053074A1 (en) 2016-09-16 2018-03-22 Bayer Healthcare Llc Pressure jacket having syringe retaining element
US11207462B2 (en) 2016-10-17 2021-12-28 Bayer Healthcare Llc Fluid injector with syringe engagement mechanism
JP7023947B2 (ja) 2016-10-17 2022-02-22 バイエル・ヘルスケア・エルエルシー シリンジ係合機構を備える流体インジェクタ
DK3681561T3 (da) 2017-09-13 2022-01-24 Bayer Healthcare Llc Forskydelig sprøjtehætte til separat fyldning og fremføring
JP2022546618A (ja) 2019-09-10 2022-11-04 バイエル・ヘルスケア・エルエルシー 血管造影流体インジェクタ用の圧力ジャケット及びシリンジ保持機構
JP2023514704A (ja) 2020-02-21 2023-04-07 バイエル・ヘルスケア・エルエルシー 医療用流体のデリバリのための流体経路コネクタ
WO2021257699A1 (en) 2020-06-18 2021-12-23 Bayer Healthcare Llc In-line air bubble suspension apparatus for angiography injector fluid paths

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8344156B2 (en) * 2008-03-18 2013-01-01 Mitsui Chemicals Agro, Inc. Method for producing fluorine-containing acylacetic acid derivative, method for producing fluorine-containing pyrazolecarboxylic acid ester derivative, and method for producing fluorine-containing pyrazolecarboxylic acid derivative
US8410117B2 (en) * 2010-03-26 2013-04-02 Hoffmann-La Roche Inc. Imidazopyrimidine derivatives

Also Published As

Publication number Publication date
EP2885276A1 (en) 2015-06-24
JP6122118B2 (ja) 2017-04-26
KR20150042847A (ko) 2015-04-21
MX2015001023A (es) 2015-04-08
US9346763B2 (en) 2016-05-24
BR112015002779A2 (pt) 2019-10-15
RU2015106856A (ru) 2016-10-10
EP2885276B1 (en) 2016-06-01
JP2015530371A (ja) 2015-10-15
CN104540807A (zh) 2015-04-22
RU2638112C2 (ru) 2017-12-15
CN104540807B (zh) 2016-09-14
WO2014027009A1 (en) 2014-02-20
HK1206358A1 (en) 2016-01-08
ES2588056T3 (es) 2016-10-28
CA2880846A1 (en) 2014-02-20
US20150158818A1 (en) 2015-06-11
BR112015002779A8 (pt) 2017-12-19

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