ZA201908267B - 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

Info

Publication number
ZA201908267B
ZA201908267B ZA201908267A ZA201908267A ZA201908267B ZA 201908267 B ZA201908267 B ZA 201908267B ZA 201908267 A ZA201908267 A ZA 201908267A ZA 201908267 A ZA201908267 A ZA 201908267A ZA 201908267 B ZA201908267 B ZA 201908267B
Authority
ZA
South Africa
Prior art keywords
acetamido
carboxamide
pyrrolidine
allyl
tert
Prior art date
Application number
ZA201908267A
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 ZA201908267B publication Critical patent/ZA201908267B/en

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Classifications

    • 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)
ZA201908267A 2017-05-12 2019-12-11 Method of preparing (3r,4s)-3-acetamido-4-allyl-n-(tert-butyl)pyrrolidine-3-carboxamide ZA201908267B (en)

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
ZA201908267B true ZA201908267B (en) 2020-11-25

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
ZA201908267A ZA201908267B (en) 2017-05-12 2019-12-11 Method of preparing (3r,4s)-3-acetamido-4-allyl-n-(tert-butyl)pyrrolidine-3-carboxamide

Country Status (21)

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

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HRP20160305T1 (hr) 2010-10-26 2016-07-01 Mars, Incorporated Borati kao inhibitori arginaze
CN114989205A (zh) 2016-12-22 2022-09-02 卡里塞拉生物科学股份公司 用于抑制精氨酸酶活性的组合物和方法
KR20200008578A (ko) * 2017-05-12 2020-01-28 칼리테라 바이오사이언시즈, 인코포레이티드 (3R,4S)-3-아세트아미도-4-알릴-N-(tert-부틸)피롤리딘-3-카복스아미드의 제조방법
WO2019186497A1 (en) 2018-03-29 2019-10-03 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
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

Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU9797998A (en) 1997-10-10 1999-05-03 Trustees Of The University Of Pennsylvania, The Compositions and methods for inhibiting arginase activity
US20040063666A1 (en) 1998-10-09 2004-04-01 David Christianson Compositions for inhibiting arginase activity
CA2415174A1 (en) 2000-07-06 2002-01-17 Thomas W. Bell 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
LT2389352T (lt) 2009-01-26 2019-06-10 The Trustees Of The University Of Pennsylvania Arginazės inhibitoriai ir naudojimo būdai
SG10201503168VA (en) 2010-04-22 2015-06-29 Mars Inc Inhibitors of arginase and their therapeutic applications
HRP20160305T1 (hr) 2010-10-26 2016-07-01 Mars, Incorporated Borati kao inhibitori arginaze
CA2824599C (en) 2010-12-31 2020-03-10 Astrazeneca Uk Limited Arginase inhibitors and methods of use thereof
WO2013059437A1 (en) 2011-10-19 2013-04-25 Mars, Incorporated Inhibitors of arginase and their therapeutic applications
JP6073343B2 (ja) 2011-10-20 2017-02-01 グラクソスミスクライン・リミテッド・ライアビリティ・カンパニーＧｌａｘｏＳｍｉｔｈＫｌｉｎｅ ＬＬＣ サーチュイン調節因子としての置換された二環式アザ複素環およびアナログ
CN104540836B (zh) * 2012-04-18 2016-11-09 马尔斯公司 作为精氨酸酶抑制剂的环约束类似物
EA201690746A1 (ru) 2013-10-25 2016-12-30 Фармасайкликс Элэлси Лечение с применением ингибиторов тирозинкиназы брутона и иммунотерапии
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
US10143699B2 (en) * 2015-06-23 2018-12-04 Calithera Biosciences, Inc. Compositions and methods for inhibiting arginase activity
SG11201802961PA (en) * 2015-10-30 2018-05-30 Calithera Biosciences Inc Compositions and methods for inhibiting arginase activity
KR20200008578A (ko) * 2017-05-12 2020-01-28 칼리테라 바이오사이언시즈, 인코포레이티드 (3R,4S)-3-아세트아미도-4-알릴-N-(tert-부틸)피롤리딘-3-카복스아미드의 제조방법

Also Published As

Publication number Publication date
MX2019013533A (es) 2020-08-03
CO2019013923A2 (es) 2020-04-01
KR20200008578A (ko) 2020-01-28
EP3621954A1 (en) 2020-03-18
EP3621954B1 (en) 2022-03-09
IL278757A (en) 2021-01-31
US20200087255A1 (en) 2020-03-19
BR112019023582A2 (pt) 2020-06-02
CL2019003212A1 (es) 2020-02-21
IL285299A (en) 2021-09-30
US20210155589A1 (en) 2021-05-27
MA48626A (fr) 2020-03-18
US20180362459A1 (en) 2018-12-20
US10906872B2 (en) 2021-02-02
CR20190562A (es) 2020-03-04
IL278757B (en) 2021-08-31
PE20200339A1 (es) 2020-02-14
AU2018265873A1 (en) 2019-11-28
WO2018209290A1 (en) 2018-11-15
JP2020519583A (ja) 2020-07-02
CA3062851A1 (en) 2018-11-15
PH12019502505A1 (en) 2020-07-13
TW201900609A (zh) 2019-01-01
US11370754B2 (en) 2022-06-28
CN110709383A (zh) 2020-01-17
SG10201912946TA (en) 2020-02-27
US10494339B2 (en) 2019-12-03
EA201992695A1 (ru) 2020-05-15

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