CR20190562A - Método para preparar (3r, 4s)-3-acetamido-4-alil-n-(terc-butil)pirrolidina-3-carboxamida - Google Patents

Método para preparar (3r, 4s)-3-acetamido-4-alil-n-(terc-butil)pirrolidina-3-carboxamida

Info

Publication number
CR20190562A
CR20190562A CR20190562A CR20190562A CR20190562A CR 20190562 A CR20190562 A CR 20190562A CR 20190562 A CR20190562 A CR 20190562A CR 20190562 A CR20190562 A CR 20190562A CR 20190562 A CR20190562 A CR 20190562A
Authority
CR
Costa Rica
Prior art keywords
acetamido
carboxamide
pyrrolidine
allyl
tert
Prior art date
Application number
CR20190562A
Other languages
English (en)
Inventor
Jennifer L Savoy
Zandt Michael C Van
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 CR20190562A publication Critical patent/CR20190562A/es

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    • 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
    • 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
    • C07D207/10—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

Landscapes

  • 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-alil-N-(terc-butil)pirrolidina-3-carboxamida racémica y (3S,4R)-3-acetamido-4-alil-N-(terc-butil)pirrolidina-3-carboxamida usando cristalización selectiva con ácidos carboxílicos quirales.
CR20190562A 2017-05-12 2018-05-11 Método para preparar (3r, 4s)-3-acetamido-4-alil-n-(terc-butil)pirrolidina-3-carboxamida CR20190562A (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
CR20190562A true CR20190562A (es) 2020-03-04

Family

ID=62387001

Family Applications (1)

Application Number Title Priority Date Filing Date
CR20190562A CR20190562A (es) 2017-05-12 2018-05-11 Método para preparar (3r, 4s)-3-acetamido-4-alil-n-(terc-butil)pirrolidina-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)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PL2632927T3 (pl) 2010-10-26 2016-09-30 Boroniany jako inhibitory arginazy
SG10201912946TA (en) * 2017-05-12 2020-02-27 Calithera Biosciences Inc Method of preparing (3r,4s)-3-acetamido-4-allyl-n-(tert-butyl)pyrrolidine-3-carboxamide
US10851099B2 (en) 2018-03-29 2020-12-01 Oncoarendi Therapeutics S.A. Dipeptide piperidine derivatives
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
US20220041630A1 (en) 2020-07-17 2022-02-10 Incyte Corporation Processes for the preparation of arginase inhibitors and their synthetic intermediates
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

Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
US6720188B2 (en) 2000-07-06 2004-04-13 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
WO2007005620A2 (en) 2005-07-01 2007-01-11 The Johns Hopkins University Arginase ii: a target treatment of aging heart and heart failure
TR201910726T4 (tr) 2009-01-26 2019-08-21 Astrazeneca Uk Ltd Arginaz inhibitörleri ve kullanım yöntemleri.
MX348422B (es) 2010-04-22 2017-06-12 Mars Inc Inhibidores de arginasa y sus aplicaciones terapeuticas.
PL2632927T3 (pl) * 2010-10-26 2016-09-30 Boroniany jako inhibitory arginazy
JP2014506253A (ja) 2010-12-31 2014-03-13 コリドー ファーマシューティカルズ インコーポレイテッド アルギナーゼ阻害剤およびその使用法
MX343534B (es) 2011-10-19 2016-11-09 Mars Inc Inhibidores de arginasa y sus aplicaciones terapeuticas.
ES2627347T3 (es) 2011-10-20 2017-07-27 Glaxosmithkline Llc Aza-heterociclos bicíclicos sustituidos y análogos como moduladores de sirtuina
AU2013249790B2 (en) * 2012-04-18 2018-01-25 Mars, Incorporated Ring constrained analogs as Arginase inhibitors
MX2016005283A (es) 2013-10-25 2017-02-20 Pharmacyclics Llc Tratamiento que utiliza inhibidores de tirosina quinasa de bruton e inmunoterapia.
CN105879030A (zh) 2014-09-30 2016-08-24 复旦大学 治疗肿瘤的增效药物复合物及其制备方法
KR20170129896A (ko) 2015-03-20 2017-11-27 새미 오유 오피요 악성 신생물에 대한 수라민 및 아르기나아제 억제제의 용도
AU2016281620B2 (en) * 2015-06-23 2021-07-22 Calithera Biosciences, Inc. Compositions and methods for inhibiting arginase activity
RS60695B1 (sr) 2015-10-30 2020-09-30 Calithera Biosciences Inc Supstance i postupci za inhibiranje aktivnosti arginaze
SG10201912946TA (en) * 2017-05-12 2020-02-27 Calithera Biosciences Inc Method of preparing (3r,4s)-3-acetamido-4-allyl-n-(tert-butyl)pyrrolidine-3-carboxamide

Also Published As

Publication number Publication date
US10494339B2 (en) 2019-12-03
IL278757A (en) 2021-01-31
US20200087255A1 (en) 2020-03-19
CL2019003212A1 (es) 2020-02-21
US20180362459A1 (en) 2018-12-20
SG10201912946TA (en) 2020-02-27
EP3621954B1 (en) 2022-03-09
MA48626A (fr) 2020-03-18
IL278757B (en) 2021-08-31
TW201900609A (zh) 2019-01-01
CO2019013923A2 (es) 2020-04-01
EP3621954A1 (en) 2020-03-18
EA201992695A1 (ru) 2020-05-15
PH12019502505A1 (en) 2020-07-13
JP2020519583A (ja) 2020-07-02
CA3062851A1 (en) 2018-11-15
PE20200339A1 (es) 2020-02-14
KR20200008578A (ko) 2020-01-28
AU2018265873A1 (en) 2019-11-28
WO2018209290A1 (en) 2018-11-15
BR112019023582A2 (pt) 2020-06-02
ZA201908267B (en) 2020-11-25
IL285299A (en) 2021-09-30
MX2019013533A (es) 2020-08-03
US10906872B2 (en) 2021-02-02
CN110709383A (zh) 2020-01-17
US11370754B2 (en) 2022-06-28
US20210155589A1 (en) 2021-05-27

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