CA3062851A1 - Method of preparing (3r,4s)-3-acetamido-4-allyl-n-(tert-butyl)pyrrolidine-3-carboxamide - Google Patents

Method of preparing (3r,4s)-3-acetamido-4-allyl-n-(tert-butyl)pyrrolidine-3-carboxamide Download PDF

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Publication number
CA3062851A1
CA3062851A1 CA3062851A CA3062851A CA3062851A1 CA 3062851 A1 CA3062851 A1 CA 3062851A1 CA 3062851 A CA3062851 A CA 3062851A CA 3062851 A CA3062851 A CA 3062851A CA 3062851 A1 CA3062851 A1 CA 3062851A1
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Prior art keywords
compound
amine compound
salt
formula
enantiomeric excess
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CA3062851A
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English (en)
French (fr)
Inventor
Michael C. Van Zandt
Jennifer L. SAVOY
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Calithera Biosciences Inc
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Calithera Biosciences Inc
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Publication of CA3062851A1 publication Critical patent/CA3062851A1/en
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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
    • C07D207/10—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
    • 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
    • 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)
CA3062851A 2017-05-12 2018-05-11 Method of preparing (3r,4s)-3-acetamido-4-allyl-n-(tert-butyl)pyrrolidine-3-carboxamide Pending CA3062851A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201762505282P 2017-05-12 2017-05-12
US62/505,282 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
CA3062851A1 true CA3062851A1 (en) 2018-11-15

Family

ID=62387001

Family Applications (1)

Application Number Title Priority Date Filing Date
CA3062851A Pending CA3062851A1 (en) 2017-05-12 2018-05-11 Method of preparing (3r,4s)-3-acetamido-4-allyl-n-(tert-butyl)pyrrolidine-3-carboxamide

Country Status (21)

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

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DK2632927T3 (en) 2010-10-26 2016-04-11 Mars Inc Boronates AS ARGINSASEINHIBITORER
SMT202100573T1 (it) 2016-12-22 2021-11-12 Calithera Biosciences Inc Composizioni e metodi per l'inibizione dell'attivita' dell'arginasi
WO2018209290A1 (en) * 2017-05-12 2018-11-15 Calithera Biosciences, Inc. Method of preparing (3r,4s)-3-acetamido-4-allyl-n-(tert-butyl)pyrrolidine-3-carboxamide
EP3774843B1 (en) 2018-03-29 2022-05-25 Molecure SA 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
WO1999019295A1 (en) 1997-10-10 1999-04-22 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
JP2004502948A (ja) 2000-07-06 2004-01-29 ファル　ダイアグノスティクス アルギニン化合物の検出のための方法及びキット
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
SI2389352T1 (sl) 2009-01-26 2019-08-30 The Trustees Of The University Of Pennsylvania, Center For Technology Transfer Inhibitorji arginaze in postopki uporabe
CN103068830B (zh) 2010-04-22 2016-06-29 马尔斯公司 精氨酸酶抑制剂及其治疗应用
DK2632927T3 (en) 2010-10-26 2016-04-11 Mars Inc Boronates AS ARGINSASEINHIBITORER
CA2824599C (en) 2010-12-31 2020-03-10 Astrazeneca Uk Limited Arginase inhibitors and methods of use thereof
US9266908B2 (en) 2011-10-19 2016-02-23 Mars, Incorporated Inhibitors of arginase and their therapeutic applications
RU2014120166A (ru) 2011-10-20 2015-11-27 ГЛЭКСОСМИТКЛАЙН ЭлЭлСи Замещенные бициклические аза-гетероциклы и их аналоги в качестве модуляторов сиртуина
CA2870526C (en) 2012-04-18 2020-05-05 Mars, Incorporated Ring constrained analogs as arginase inhibitors
JP6508785B2 (ja) 2013-10-25 2019-05-08 ファーマサイクリックス エルエルシー ブルトンチロシンキナーゼ阻害剤および免疫療法を使用する処置
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
CN107405404A (zh) 2015-03-20 2017-11-28 塞米·欧尤·奥皮约 苏拉明和精氨酸酶抑制剂在恶性肿瘤中的用途
KR20180021117A (ko) 2015-06-23 2018-02-28 칼리테라 바이오사이언시즈, 인코포레이티드 아르기나제 활성 억제를 위한 조성물 및 방법
WO2017075363A1 (en) * 2015-10-30 2017-05-04 Calithera Biosciences, Inc. Compositions and methods for inhibiting arginase activity
WO2018209290A1 (en) * 2017-05-12 2018-11-15 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
JP2020519583A (ja) 2020-07-02
US11370754B2 (en) 2022-06-28
US20210155589A1 (en) 2021-05-27
PH12019502505A1 (en) 2020-07-13
IL278757B (en) 2021-08-31
EP3621954B1 (en) 2022-03-09
US20180362459A1 (en) 2018-12-20
ZA201908267B (en) 2020-11-25
TW201900609A (zh) 2019-01-01
WO2018209290A1 (en) 2018-11-15
EA201992695A1 (ru) 2020-05-15
EP3621954A1 (en) 2020-03-18
US20200087255A1 (en) 2020-03-19
US10906872B2 (en) 2021-02-02
CR20190562A (es) 2020-03-04
CL2019003212A1 (es) 2020-02-21
CN110709383A (zh) 2020-01-17
AU2018265873A1 (en) 2019-11-28
IL278757A (en) 2021-01-31
SG10201912946TA (en) 2020-02-27
BR112019023582A2 (pt) 2020-06-02
PE20200339A1 (es) 2020-02-14
IL285299A (en) 2021-09-30
CO2019013923A2 (es) 2020-04-01
KR20200008578A (ko) 2020-01-28
US10494339B2 (en) 2019-12-03
MX2019013533A (es) 2020-08-03
MA48626A (fr) 2020-03-18

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