KR102719583B1 - 테리플루노미드의 신규한 제조 공정 - Google Patents

테리플루노미드의 신규한 제조 공정 Download PDF

Info

Publication number
KR102719583B1
KR102719583B1 KR1020187000970A KR20187000970A KR102719583B1 KR 102719583 B1 KR102719583 B1 KR 102719583B1 KR 1020187000970 A KR1020187000970 A KR 1020187000970A KR 20187000970 A KR20187000970 A KR 20187000970A KR 102719583 B1 KR102719583 B1 KR 102719583B1
Authority
KR
South Korea
Prior art keywords
formula
chemical formula
trifluoromethylphenyl
methylisoxazole
water
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.)
Active
Application number
KR1020187000970A
Other languages
English (en)
Korean (ko)
Other versions
KR20180018697A (ko
Inventor
벤카다 라가번드라챠리우루 팔레
라마크리쉬나 파라메쉬왈 바트
지센드라 알. 바부
라마헨드라 샨무가사미
마리아빤 카리아빤
Original Assignee
바이오콘 리미티드
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 바이오콘 리미티드 filed Critical 바이오콘 리미티드
Publication of KR20180018697A publication Critical patent/KR20180018697A/ko
Application granted granted Critical
Publication of KR102719583B1 publication Critical patent/KR102719583B1/ko
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/14—Preparation of carboxylic acid nitriles by reaction of cyanides with halogen-containing compounds with replacement of halogen atoms by cyano groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/32—Separation; Purification; Stabilisation; Use of additives
    • C07C253/34—Separation; Purification
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/23—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and carboxyl groups, other than cyano groups, bound to the same unsaturated acyclic carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/41—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by carboxyl groups, other than cyano groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/42—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being further bound to other hetero atoms
    • C07C255/43—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being further bound to other hetero atoms the carbon skeleton being further substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N23/00—Investigating or analysing materials by the use of wave or particle radiation, e.g. X-rays or neutrons, not covered by groups G01N3/00 – G01N17/00, G01N21/00 or G01N22/00
    • G01N23/20—Investigating or analysing materials by the use of wave or particle radiation, e.g. X-rays or neutrons, not covered by groups G01N3/00 – G01N17/00, G01N21/00 or G01N22/00 by using diffraction of the radiation by the materials, e.g. for investigating crystal structure; by using scattering of the radiation by the materials, e.g. for investigating non-crystalline materials; by using reflection of the radiation by the materials
    • G01N23/20075—Investigating or analysing materials by the use of wave or particle radiation, e.g. X-rays or neutrons, not covered by groups G01N3/00 – G01N17/00, G01N21/00 or G01N22/00 by using diffraction of the radiation by the materials, e.g. for investigating crystal structure; by using scattering of the radiation by the materials, e.g. for investigating non-crystalline materials; by using reflection of the radiation by the materials by measuring interferences of X-rays, e.g. Borrmann effect
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N25/00—Investigating or analyzing materials by the use of thermal means
    • G01N25/20—Investigating or analyzing materials by the use of thermal means by investigating the development of heat, i.e. calorimetry, e.g. by measuring specific heat, by measuring thermal conductivity
    • G01N25/48—Investigating or analyzing materials by the use of thermal means by investigating the development of heat, i.e. calorimetry, e.g. by measuring specific heat, by measuring thermal conductivity on solution, sorption, or a chemical reaction not involving combustion or catalytic oxidation
    • G01N25/4846—Investigating or analyzing materials by the use of thermal means by investigating the development of heat, i.e. calorimetry, e.g. by measuring specific heat, by measuring thermal conductivity on solution, sorption, or a chemical reaction not involving combustion or catalytic oxidation for a motionless, e.g. solid sample
    • G01N25/4866—Investigating or analyzing materials by the use of thermal means by investigating the development of heat, i.e. calorimetry, e.g. by measuring specific heat, by measuring thermal conductivity on solution, sorption, or a chemical reaction not involving combustion or catalytic oxidation for a motionless, e.g. solid sample by using a differential method
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01R—MEASURING ELECTRIC VARIABLES; MEASURING MAGNETIC VARIABLES
    • G01R33/00—Arrangements or instruments for measuring magnetic variables
    • G01R33/20—Arrangements or instruments for measuring magnetic variables involving magnetic resonance
    • G01R33/44—Arrangements or instruments for measuring magnetic variables involving magnetic resonance using nuclear magnetic resonance [NMR]
    • G01R33/46—NMR spectroscopy

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Toxicology (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
KR1020187000970A 2015-06-17 2016-06-16 테리플루노미드의 신규한 제조 공정 Active KR102719583B1 (ko)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
IN3028/CHE/2015 2015-06-17
IN3028CH2015 2015-06-17
PCT/IB2016/053556 WO2016203410A1 (en) 2015-06-17 2016-06-16 A novel process for the preparation of teriflunomide

Publications (2)

Publication Number Publication Date
KR20180018697A KR20180018697A (ko) 2018-02-21
KR102719583B1 true KR102719583B1 (ko) 2024-10-18

Family

ID=57545389

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1020187000970A Active KR102719583B1 (ko) 2015-06-17 2016-06-16 테리플루노미드의 신규한 제조 공정

Country Status (11)

Country Link
US (1) US10526279B2 (https=)
EP (1) EP3310755B1 (https=)
JP (1) JP6797839B2 (https=)
KR (1) KR102719583B1 (https=)
AU (1) AU2016280243B2 (https=)
BR (1) BR112017027175B1 (https=)
CA (1) CA2989394C (https=)
ES (1) ES2870205T3 (https=)
MX (1) MX2017016192A (https=)
RU (1) RU2722316C2 (https=)
WO (1) WO2016203410A1 (https=)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116924938B (zh) * 2022-04-02 2025-10-31 江苏康缘药业股份有限公司 一种特立氟胺的制备方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015029063A2 (en) * 2013-08-30 2015-03-05 Msn Laboratories Private Limited Novel polymorph of (z)-2-cyano-3-hydroxy-but-2-enoic acid-(4-trifluoromethyl phenyl)-amide and process for the preparation thereof

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE634286C (de) 1935-02-23 1936-08-26 Hoffmann La Roche & Co Akt Ges Verfahren zur Herstellung dialkylsubstituierter Amide von Isoxazolcarbonsaeuren
NL186239B (nl) * 1975-06-05 Hoechst Ag Werkwijze voor de bereiding van een geneesmiddel met antiflogistische en/of analgetische werking, alsmede werkwijze voor de bereiding van een 2-hydroxyethylideencyaanazijnzuuranilide geschikt voor toepassing bij deze werkwijze.
US5268382A (en) 1985-09-27 1993-12-07 Hoechst Aktiengesellschaft Medicaments to combat autoimmune diseases, in particular systemic lupus erythematosus
ES2102367T3 (es) * 1990-05-18 1997-08-01 Hoechst Ag Amidas de acidos isoxazol-4-carboxilicos y amidas de acidos hidroxialquiliden-cianoaceticos, medicamentos que contienen estos compuestos y su utilizacion.
ES2237553T3 (es) * 2000-02-15 2005-08-01 Teva Pharmaceutical Industries Ltd. Procedimiento para la sintesis de leflunomida.
US6727272B1 (en) * 2002-07-15 2004-04-27 Unitech Pharmaceuticals, Inc. Leflunomide analogs for treating rheumatoid arthritis
CA2724861A1 (en) * 2008-06-05 2009-12-10 Alembic Limited A process for preparing teriflunomide
CN101817798B (zh) * 2009-02-26 2014-04-16 江苏亚邦爱普森药业有限公司 制备来氟米特的绿色工艺
WO2012110911A1 (en) * 2011-02-18 2012-08-23 Alembic Pharmaceuticals Limited Novel polymorphic form of teriflunomide

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015029063A2 (en) * 2013-08-30 2015-03-05 Msn Laboratories Private Limited Novel polymorph of (z)-2-cyano-3-hydroxy-but-2-enoic acid-(4-trifluoromethyl phenyl)-amide and process for the preparation thereof

Also Published As

Publication number Publication date
EP3310755A4 (en) 2019-02-27
RU2722316C2 (ru) 2020-05-29
MX2017016192A (es) 2018-06-19
EP3310755A1 (en) 2018-04-25
BR112017027175B1 (pt) 2022-02-08
JP2018517733A (ja) 2018-07-05
CA2989394C (en) 2023-08-01
BR112017027175A2 (https=) 2017-12-15
CA2989394A1 (en) 2016-12-22
AU2016280243A1 (en) 2018-01-18
WO2016203410A1 (en) 2016-12-22
ES2870205T3 (es) 2021-10-26
JP6797839B2 (ja) 2020-12-09
RU2017145967A (ru) 2019-07-18
KR20180018697A (ko) 2018-02-21
AU2016280243B2 (en) 2020-12-03
US10526279B2 (en) 2020-01-07
RU2017145967A3 (https=) 2019-12-06
US20180170859A1 (en) 2018-06-21
EP3310755B1 (en) 2021-02-24

Similar Documents

Publication Publication Date Title
AU2014339136B2 (en) Process for the preparation of a PDE4 inhibitor
JP5161023B2 (ja) ピペラジン誘導体の製造方法
US10927095B2 (en) Processes for the preparation of Niraparib and intermediates thereof
WO2014020555A2 (en) An improved process for the preparation of dabigatran etexilate mesylate
CN107922352A (zh) 制备蛋白质脱乙酰酶抑制剂的方法
JP2021169497A (ja) 高純度２−ナフチルアセトニトリル及びその製造方法
KR102719583B1 (ko) 테리플루노미드의 신규한 제조 공정
WO2023073502A1 (en) Methods for preparation of anthranilamide and pyrazole-carboxylate intermediate compounds
WO2019208807A1 (ja) 芳香族ニトリル化合物の製造方法
CA2127945C (en) Process of producing 2-cyano-4-oxo-4h-benzopyran compounds
KR101744046B1 (ko) 실로도신 합성에 유용한 중간체의 제조방법
CN107673994A (zh) 一种芳基甲烷类化合物的制备方法
JP6763401B2 (ja) ベンズオキサゾール化合物の製造方法
JPH06199759A (ja) フェニル酢酸誘導体の製造方法
KR20190049883A (ko) 페닐알라닌 화합물의 제조 방법
JP2011042602A (ja) ２−（３−ニトロベンジリデン）アセト酢酸イソプロピルの製造方法
TWI920144B (zh) 八氫噻吩并喹啉化合物之製造方法及其製造中間體
KR20230032513A (ko) 카모스타트 메실산염의 제조방법
TW202535810A (zh) 經取代苯基乙腈及經取代苯基醋酸之製備方法
JP4228145B2 (ja) 芳香族ニトリル誘導体の製造方法
JP2025517548A (ja) ４－置換２－オキサゾリジノンの調製プロセス
JP2004075616A (ja) ４−ハロゲノ−２−（４−フルオロフェニルアミノ）−５，６−ジメチルピリミジンの製造方法
WO2008026527A1 (fr) Procédé de fabrication d'un dérivé de 3-cyanopyrrolidine ou d'un de ses sels
JP2006315972A (ja) ３−アミノイソオキサゾールの硫酸塩及びその製法

Legal Events

Date Code Title Description
PA0105 International application

Patent event date: 20180111

Patent event code: PA01051R01D

Comment text: International Patent Application

PG1501 Laying open of application
A201 Request for examination
PA0201 Request for examination

Patent event code: PA02012R01D

Patent event date: 20210608

Comment text: Request for Examination of Application

E902 Notification of reason for refusal
PE0902 Notice of grounds for rejection

Comment text: Notification of reason for refusal

Patent event date: 20240125

Patent event code: PE09021S01D

E701 Decision to grant or registration of patent right
PE0701 Decision of registration

Patent event code: PE07011S01D

Comment text: Decision to Grant Registration

Patent event date: 20241007

GRNT Written decision to grant
PR0701 Registration of establishment

Comment text: Registration of Establishment

Patent event date: 20241015

Patent event code: PR07011E01D

PR1002 Payment of registration fee

Payment date: 20241016

End annual number: 3

Start annual number: 1

PG1601 Publication of registration