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MX2019013533A - Metodo para preparar (3r,4s)-3-acetamido-4-alil-n-(terc-butil)pirr olidina-3-carboxamida. - Google Patents

Metodo para preparar (3r,4s)-3-acetamido-4-alil-n-(terc-butil)pirr olidina-3-carboxamida.

Info

Publication number
MX2019013533A
MX2019013533A MX2019013533A MX2019013533A MX2019013533A MX 2019013533 A MX2019013533 A MX 2019013533A MX 2019013533 A MX2019013533 A MX 2019013533A MX 2019013533 A MX2019013533 A MX 2019013533A MX 2019013533 A MX2019013533 A MX 2019013533A
Authority
MX
Mexico
Prior art keywords
acetamido
allyl
tert
butyl
carboxamide
Prior art date
Application number
MX2019013533A
Other languages
English (en)
Inventor
Zandt Michael C Van
Jennifer L Savoy
Original Assignee
Calithera Biosciences Inc
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 Calithera Biosciences Inc filed Critical Calithera Biosciences Inc
Publication of MX2019013533A publication Critical patent/MX2019013533A/es

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B57/00—Separation of optically-active compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/22—Separation; Purification; Stabilisation; Use of additives
    • C07C231/24—Separation; Purification
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C233/04—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C233/05—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/57—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C233/65—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C235/06—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C327/00—Thiocarboxylic acids
    • C07C327/20—Esters of monothiocarboxylic acids
    • C07C327/22—Esters of monothiocarboxylic acids having carbon atoms of esterified thiocarboxyl groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
    • C07D207/06—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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 radicals, containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
    • C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/025—Boronic and borinic acid compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyrrole Compounds (AREA)

Abstract

Se proporciona un método para separar convenientemente (3R,4S)-3-acetamido-4-aliI-N-(terc-butil)pirrolidina-3-carboxamid a racémica y (3S,4R)-3-acetamido-4-alil-N-(terc-butil)pirrolidina- 3-carboxamida usando cristalización selectiva con ácidos carboxílicos quirales.
MX2019013533A 2017-05-12 2018-05-11 Metodo para preparar (3r,4s)-3-acetamido-4-alil-n-(terc-butil)pirr olidina-3-carboxamida. MX2019013533A (es)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201762505282P 2017-05-12 2017-05-12
PCT/US2018/032407 WO2018209290A1 (en) 2017-05-12 2018-05-11 Method of preparing (3r,4s)-3-acetamido-4-allyl-n-(tert-butyl)pyrrolidine-3-carboxamide

Publications (1)

Publication Number Publication Date
MX2019013533A true MX2019013533A (es) 2020-08-03

Family

ID=62387001

Family Applications (1)

Application Number Title Priority Date Filing Date
MX2019013533A MX2019013533A (es) 2017-05-12 2018-05-11 Metodo para preparar (3r,4s)-3-acetamido-4-alil-n-(terc-butil)pirr olidina-3-carboxamida.

Country Status (21)

Country Link
US (3) US10494339B2 (es)
EP (1) EP3621954B1 (es)
JP (1) JP2020519583A (es)
KR (1) KR20200008578A (es)
CN (1) CN110709383A (es)
AU (1) AU2018265873A1 (es)
BR (1) BR112019023582A2 (es)
CA (1) CA3062851A1 (es)
CL (1) CL2019003212A1 (es)
CO (1) CO2019013923A2 (es)
CR (1) CR20190562A (es)
EA (1) EA201992695A1 (es)
IL (2) IL278757B (es)
MA (1) MA48626A (es)
MX (1) MX2019013533A (es)
PE (1) PE20200339A1 (es)
PH (1) PH12019502505A1 (es)
SG (1) SG10201912946TA (es)
TW (1) TW201900609A (es)
WO (1) WO2018209290A1 (es)
ZA (1) ZA201908267B (es)

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Publication number Priority date Publication date Assignee Title
JP5909239B2 (ja) 2010-10-26 2016-04-26 マーズ インコーポレイテッド アルギナーゼ阻害剤としてのボロネート
MX378460B (es) 2016-12-22 2025-03-10 Calithera Biosciences Inc Composiciones y métodos para inhibir la actividad de la arginasa.
MX2019013533A (es) * 2017-05-12 2020-08-03 Calithera Biosciences Inc Metodo para preparar (3r,4s)-3-acetamido-4-alil-n-(terc-butil)pirr olidina-3-carboxamida.
TWI723366B (zh) 2018-03-29 2021-04-01 波蘭商昂科艾倫迪治療法股份公司 二肽哌啶衍生物
CN110734456A (zh) * 2019-11-06 2020-01-31 南京谷睿生物科技有限公司 一种化合物及其制备方法和医药上的应用
TW202216662A (zh) 2020-07-17 2022-05-01 美商英塞特公司 製備精胺酸酶抑制劑及其合成中間物之方法
CN113866289A (zh) * 2021-09-03 2021-12-31 上海凌凯医药科技有限公司 2,3-二苯甲酰氧基-4-二甲基氨基-4-氧代丁酸的手性分离检测方法

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EP1049660A1 (en) 1997-10-10 2000-11-08 The Trustees Of The University Of Pennsylvania Compositions and methods for inhibiting arginase activity
US20040063666A1 (en) 1998-10-09 2004-04-01 David Christianson Compositions for inhibiting arginase activity
WO2002004465A1 (en) 2000-07-06 2002-01-17 Fal Diagnostics Methods and kits for the detection of arginine compounds
CA2431080A1 (en) 2003-06-02 2004-12-02 Catherine Adele O'brien Enhancement of anticancer immunity through inhibition of arginase
EP1915143A4 (en) 2005-07-01 2009-11-11 Univ Johns Hopkins ARGINASE II: TARGET TREATMENT FOR THE AGING HEART AND HEART FAILURE
DK2389352T3 (da) 2009-01-26 2019-07-29 Univ Pennsylvania Arginaseinhibitorer og anvendelsesfremgangsmåder
NZ603364A (en) 2010-04-22 2015-06-26 Mars Inc Inhibitors of arginase and their therapeutic applications
JP5909239B2 (ja) * 2010-10-26 2016-04-26 マーズ インコーポレイテッド アルギナーゼ阻害剤としてのボロネート
CN104857005B (zh) 2010-12-31 2019-04-26 阿斯利康公司 精氨酸酶抑制剂及其使用方法
WO2013059437A1 (en) 2011-10-19 2013-04-25 Mars, Incorporated Inhibitors of arginase and their therapeutic applications
ES2627347T3 (es) 2011-10-20 2017-07-27 Glaxosmithkline Llc Aza-heterociclos bicíclicos sustituidos y análogos como moduladores de sirtuina
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AU2014339816B2 (en) 2013-10-25 2020-05-28 Pharmacyclics Llc Treatment using Bruton's tyrosine kinase inhibitors and immunotherapy
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KR20170129896A (ko) 2015-03-20 2017-11-27 새미 오유 오피요 악성 신생물에 대한 수라민 및 아르기나아제 억제제의 용도
MA42269A (fr) 2015-06-23 2018-05-02 Calithera Biosciences Inc Compositions et procédés d'inhibition de l'activité de l'arginase
ES2808988T3 (es) 2015-10-30 2021-03-02 Calithera Biosciences Inc Composiciones y métodos para inhibir la actividad arginasa
MX2019013533A (es) * 2017-05-12 2020-08-03 Calithera Biosciences Inc Metodo para preparar (3r,4s)-3-acetamido-4-alil-n-(terc-butil)pirr olidina-3-carboxamida.

Also Published As

Publication number Publication date
US10494339B2 (en) 2019-12-03
IL278757B (en) 2021-08-31
US20180362459A1 (en) 2018-12-20
CO2019013923A2 (es) 2020-04-01
CL2019003212A1 (es) 2020-02-21
US10906872B2 (en) 2021-02-02
US20210155589A1 (en) 2021-05-27
TW201900609A (zh) 2019-01-01
JP2020519583A (ja) 2020-07-02
IL285299A (en) 2021-09-30
EA201992695A1 (ru) 2020-05-15
MA48626A (fr) 2020-03-18
AU2018265873A1 (en) 2019-11-28
US11370754B2 (en) 2022-06-28
SG10201912946TA (en) 2020-02-27
PH12019502505A1 (en) 2020-07-13
EP3621954B1 (en) 2022-03-09
WO2018209290A1 (en) 2018-11-15
ZA201908267B (en) 2020-11-25
BR112019023582A2 (pt) 2020-06-02
PE20200339A1 (es) 2020-02-14
CA3062851A1 (en) 2018-11-15
IL278757A (en) 2021-01-31
US20200087255A1 (en) 2020-03-19
KR20200008578A (ko) 2020-01-28
CN110709383A (zh) 2020-01-17
EP3621954A1 (en) 2020-03-18
CR20190562A (es) 2020-03-04

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