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MX362290B - Un proceso mejorado para la preparacion de (3r,4r)-(1-bencilo-4-me tilpiperidina-3-il)-metilamina. - Google Patents

Un proceso mejorado para la preparacion de (3r,4r)-(1-bencilo-4-me tilpiperidina-3-il)-metilamina.

Info

Publication number
MX362290B
MX362290B MX2015015432A MX2015015432A MX362290B MX 362290 B MX362290 B MX 362290B MX 2015015432 A MX2015015432 A MX 2015015432A MX 2015015432 A MX2015015432 A MX 2015015432A MX 362290 B MX362290 B MX 362290B
Authority
MX
Mexico
Prior art keywords
benzyl
methylamine
methylpiperidin
preparation
methyl pyridine
Prior art date
Application number
MX2015015432A
Other languages
English (en)
Other versions
MX2015015432A (es
Inventor
Dhananjay G Sathe
Arijit Das
Yogesh Subhash Patil
Nilesh L Bonde
Ankush Sampat Kekan
Original Assignee
Unichem Lab Ltd
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 Unichem Lab Ltd filed Critical Unichem Lab Ltd
Publication of MX2015015432A publication Critical patent/MX2015015432A/es
Publication of MX362290B publication Critical patent/MX362290B/es

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/02—Preparation by ring-closure or hydrogenation
    • 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
    • C07D211/56—Nitrogen atoms
    • 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
    • C07D211/68—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 one double bond between ring members or between a ring member and a non-ring member
    • C07D211/72—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 one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
    • C07D211/98—Nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Hydrogenated Pyridines (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

La presente invención se refiere a un proceso mejorado y eficiente para la preparación de (3R,4R)-(1-bencilo-4-metilo-piper idina-3-il)-metilamina que comprende: (a) N-acilación de 3-amino-4-metil piridina; (b) cuaternización de 3-acetilamino-4-metil piridina utilizando haluro de bencilo; (c) reducción parcial de 3-acetilamino- 4-metil piridina cuaternizada mediante borohidruro de sodio en metanol o agua; (d) hidrólisis del producto parcialmente reducido a 1-bencilo-4-metilpiperidina-3 -ona en presencia de ácido; (e) aminación reductora de 1-bencilo-4-metilpiperidina-3-ona utilizando metilamina metanólica en presencia de isopropóxido de titanio (IV) en metanol; (f) resolución de 1-bencilo-4-metilpiperidina-3-il)-metil amina utilizando ácido ditoluoil (L) tartárico para obtener (3R,4R-1-bencilo-4-metilpiperidina-3-il)-metilamina. La invención también se refiere a productos intermedios novedosos. (ver Formulas) en donde R, R' y X son como se describen en la descripción.
MX2015015432A 2013-12-09 2014-12-02 Un proceso mejorado para la preparacion de (3r,4r)-(1-bencilo-4-me tilpiperidina-3-il)-metilamina. MX362290B (es)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
PCT/IB2014/066510 WO2015087201A1 (en) 2013-12-09 2014-12-02 An improved process for the preparation of (3r,4r)-(1-benzyl-4-methylpiperidin-3-yl)-methylamine
IN3843MU2013 IN2013MU03843A (es) 2013-12-09 2014-12-02

Publications (2)

Publication Number Publication Date
MX2015015432A MX2015015432A (es) 2016-03-15
MX362290B true MX362290B (es) 2019-01-10

Family

ID=53370688

Family Applications (1)

Application Number Title Priority Date Filing Date
MX2015015432A MX362290B (es) 2013-12-09 2014-12-02 Un proceso mejorado para la preparacion de (3r,4r)-(1-bencilo-4-me tilpiperidina-3-il)-metilamina.

Country Status (14)

Country Link
US (4) US9951012B2 (es)
EP (2) EP3539965B1 (es)
JP (1) JP6368794B2 (es)
BR (1) BR112015025543B1 (es)
ES (2) ES2720066T3 (es)
HU (2) HUE042911T2 (es)
IN (1) IN2013MU03843A (es)
MX (1) MX362290B (es)
PL (2) PL2994454T3 (es)
PT (2) PT2994454T (es)
SI (2) SI2994454T1 (es)
TR (1) TR201904767T4 (es)
WO (1) WO2015087201A1 (es)
ZA (1) ZA201506551B (es)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015087201A1 (en) * 2013-12-09 2015-06-18 Unichem Laboratories Limited An improved process for the preparation of (3r,4r)-(1-benzyl-4-methylpiperidin-3-yl)-methylamine
CN108349977B (zh) 2015-01-20 2021-05-25 无锡福祈制药有限公司 Jak抑制剂
EA036058B1 (ru) 2015-04-29 2020-09-21 Уси Форчун Фармасьютикал Ко., Лтд Ингибитор jak
US10174056B2 (en) 2015-05-29 2019-01-08 Wuxi Fortune Pharmaceutical Co., Ltd Substituted pyrrolo[2,3-d]pyrimidines as janus kinase inhibitors
CN105237463B (zh) * 2015-10-09 2017-10-10 刘卫国 一种(3r,4r)‑(1‑苄基‑4‑甲基哌啶‑3‑基)甲胺‑l‑二对甲苯甲酰酒石酸盐的制备方法
CN105884781B (zh) * 2016-04-18 2018-04-20 山东罗欣药业集团股份有限公司 一种枸橼酸托法替布的制备方法
EP3301087A1 (en) * 2016-09-30 2018-04-04 DPx Fine Chemicals Austria GmbH & Co KG Process for preparing chiral amines
CN107056681B (zh) * 2017-03-30 2019-10-01 广州白云山光华制药股份有限公司 一种托法替布中间体的制备方法
CN110668995A (zh) * 2018-07-03 2020-01-10 江苏海悦康医药科技有限公司 一种枸橼酸托法替布中间体及枸橼酸托法替布的制备方法
CN112645866B (zh) * 2020-12-22 2024-03-22 浙江奥翔药业股份有限公司 1-苄基-4-甲基-5-烷氧基-1,2,3,6-四氢吡啶衍生物的合成及应用
CN114685515A (zh) * 2022-03-15 2022-07-01 上海蓝乐鸟实业有限公司 一种托法替尼的制备方法
CN115872923B (zh) * 2022-12-29 2023-04-28 成都泰和伟业生物科技有限公司 一种化合物及其制备方法

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JPH06145144A (ja) 1992-11-04 1994-05-24 Ihara Chem Ind Co Ltd 新規な３−アミノピリジン誘導体第４級アンモニウム塩及びこれを有効成分とする抗癌剤
JP4671079B2 (ja) * 1999-07-05 2011-04-13 日本農薬株式会社 フタラミド誘導体、その中間体及び農園芸用殺虫剤並びにその使用方法
KR100496940B1 (ko) * 1999-10-20 2005-06-23 다나베 세이야꾸 가부시키가이샤 αＬβ2 개재된 세포 접착 억제제
AP1905A (en) 1999-12-10 2008-10-20 Pfizer Prod Inc Pyrrolo[2,3-d] Pyrimidine Compounds.
ATE430749T1 (de) 2001-02-24 2009-05-15 Boehringer Ingelheim Pharma Xanthinderivate verwendung als arzneimittel sowie deren verfahren zur deren herstellung
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GT200200234A (es) * 2001-12-06 2003-06-27 Compuestos cristalinos novedosos
WO2006067446A1 (en) * 2004-12-22 2006-06-29 Astrazeneca Ab Pyridine carboxamide derivatives for use as anticancer agents
US8232394B2 (en) 2005-07-29 2012-07-31 Pfizer Inc. Pyrrolo[2,3-d]pyrimidine derivatives; their intermediates and synthesis
WO2008029237A2 (en) * 2006-09-05 2008-03-13 Pfizer Products Inc. Combination therapies for rheumatoid arthritis
MX2011001259A (es) * 2008-08-01 2011-03-15 Biocryst Pharm Inc Derivados de piperidina como inhibidores jak3.
US20120034250A1 (en) 2009-04-14 2012-02-09 Astellas Pharma Inc. Condensed pyrrolopyridine derivative
BRPI1007737A2 (pt) * 2009-04-20 2015-09-01 Auspex Pharmaceuticals Llc "composto da fórmula estrutural i, composição farmacêutica, método de tratamento de um distúbio mediano por janus quinase 3, método de preparação de um composto da fórmula estrutural ii, e método de preparação de um composto da fórmula estrutural xii"
US20120225862A1 (en) * 2009-07-21 2012-09-06 Auckland Univservices Limited Heteroaryl benzamides, compositions and methods of use
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WO2015087201A1 (en) * 2013-12-09 2015-06-18 Unichem Laboratories Limited An improved process for the preparation of (3r,4r)-(1-benzyl-4-methylpiperidin-3-yl)-methylamine

Also Published As

Publication number Publication date
HUE042911T2 (hu) 2019-07-29
SI3539965T1 (sl) 2021-07-30
US9951012B2 (en) 2018-04-24
BR112015025543A2 (pt) 2017-07-18
JP2017503007A (ja) 2017-01-26
MX2015015432A (es) 2016-03-15
WO2015087201A1 (en) 2015-06-18
EP3539965B1 (en) 2021-01-20
US20170240510A1 (en) 2017-08-24
PL3539965T3 (pl) 2021-07-05
HUE053975T2 (hu) 2021-08-30
ES2720066T3 (es) 2019-07-17
EP2994454B1 (en) 2019-03-06
TR201904767T4 (tr) 2019-05-21
US20180134661A1 (en) 2018-05-17
PL2994454T3 (pl) 2019-09-30
ES2865058T3 (es) 2021-10-14
EP2994454A1 (en) 2016-03-16
PT3539965T (pt) 2021-04-07
ZA201506551B (en) 2017-02-22
US20160102057A1 (en) 2016-04-14
PT2994454T (pt) 2019-04-02
EP2994454A4 (en) 2016-12-21
EP3539965A1 (en) 2019-09-18
SI2994454T1 (sl) 2019-05-31
US20180037551A1 (en) 2018-02-08
US10829450B2 (en) 2020-11-10
IN2013MU03843A (es) 2015-08-14
BR112015025543B1 (pt) 2020-11-03
JP6368794B2 (ja) 2018-08-01

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