CA2989394C - A novel process for the preparation of teriflunomide - Google Patents

A novel process for the preparation of teriflunomide Download PDF

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Publication number
CA2989394C
CA2989394C CA2989394A CA2989394A CA2989394C CA 2989394 C CA2989394 C CA 2989394C CA 2989394 A CA2989394 A CA 2989394A CA 2989394 A CA2989394 A CA 2989394A CA 2989394 C CA2989394 C CA 2989394C
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Canada
Prior art keywords
formula
compound
water
process according
cyano
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CA2989394A
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English (en)
French (fr)
Other versions
CA2989394A1 (en
Inventor
Venkata Raghavendracharyulu PALLE
Ramakrishna Parameshwar BHAT
Mariappan KALIAPPAN
Jithendra R. BABU
Rajmahendra SHANMUGHASAMY
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Biocon Ltd
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Biocon Ltd
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Publication of CA2989394A1 publication Critical patent/CA2989394A1/en
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Publication of CA2989394C publication Critical patent/CA2989394C/en
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Classifications

    • 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
    • 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
    • C07C255/32—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)
CA2989394A 2015-06-17 2016-06-16 A novel process for the preparation of teriflunomide Active CA2989394C (en)

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
CA2989394A1 CA2989394A1 (en) 2016-12-22
CA2989394C true CA2989394C (en) 2023-08-01

Family

ID=57545389

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2989394A Active CA2989394C (en) 2015-06-17 2016-06-16 A novel process for the preparation of teriflunomide

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

Family Cites Families (10)

* 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
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
KR102719583B1 (ko) 2024-10-18
EP3310755A1 (en) 2018-04-25
BR112017027175B1 (pt) 2022-02-08
JP2018517733A (ja) 2018-07-05
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

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