CA3127220C - SYNTHESIS OF 4-CHLOROKYNURENINS AND INTERMEDIARIES - Google Patents

SYNTHESIS OF 4-CHLOROKYNURENINS AND INTERMEDIARIES

Info

Publication number
CA3127220C
CA3127220C CA3127220A CA3127220A CA3127220C CA 3127220 C CA3127220 C CA 3127220C CA 3127220 A CA3127220 A CA 3127220A CA 3127220 A CA3127220 A CA 3127220A CA 3127220 C CA3127220 C CA 3127220C
Authority
CA
Canada
Prior art keywords
reactor
minutes
chlorokynurenine
absence
reaction conditions
Prior art date
Legal status (The legal status 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 status listed.)
Active
Application number
CA3127220A
Other languages
English (en)
French (fr)
Other versions
CA3127220A1 (en
Inventor
Daniel Levin
Peter Leeming
Emerich Eisenreich
Xuejun Karl Liu
Original Assignee
Vistagen Therapeutics 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 Vistagen Therapeutics Inc filed Critical Vistagen Therapeutics Inc
Publication of CA3127220A1 publication Critical patent/CA3127220A1/en
Application granted granted Critical
Publication of CA3127220C publication Critical patent/CA3127220C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
    • C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
    • C07C227/16—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions not involving the amino or carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
    • C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
    • C07C227/20—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters by hydrolysis of N-acylated amino-acids or derivatives thereof, e.g. hydrolysis of carbamates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/30—Preparation of optical isomers
    • C07C227/32—Preparation of optical isomers by stereospecific synthesis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/38—Separation; Purification; Stabilisation; Use of additives
    • C07C227/40—Separation; Purification
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C07C229/36—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings with at least one amino group and one carboxyl group bound to the same carbon atom of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/40—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to carbon atoms of at least one six-membered aromatic ring and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/42—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to carbon atoms of at least one six-membered aromatic ring and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton with carboxyl groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by saturated carbon chains
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C269/06—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups by reactions not involving the formation of carbamate groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/26—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
    • C07C303/28—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids by reaction of hydroxy compounds with sulfonic acids or derivatives thereof
    • 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
    • C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
    • C07F3/06—Zinc 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
CA3127220A 2018-02-09 2019-02-11 SYNTHESIS OF 4-CHLOROKYNURENINS AND INTERMEDIARIES Active CA3127220C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201862628580P 2018-02-09 2018-02-09
US62/628,580 2018-02-09
PCT/US2019/017448 WO2019157426A1 (en) 2018-02-09 2019-02-11 Synthesis of 4-chlorokynurenines and intermediates

Publications (2)

Publication Number Publication Date
CA3127220A1 CA3127220A1 (en) 2019-08-15
CA3127220C true CA3127220C (en) 2024-11-19

Family

ID=67548039

Family Applications (1)

Application Number Title Priority Date Filing Date
CA3127220A Active CA3127220C (en) 2018-02-09 2019-02-11 SYNTHESIS OF 4-CHLOROKYNURENINS AND INTERMEDIARIES

Country Status (6)

Country Link
US (1) US11427530B2 (https=)
EP (1) EP3749638B1 (https=)
JP (1) JP7431163B2 (https=)
CN (2) CN112236412B (https=)
CA (1) CA3127220C (https=)
WO (1) WO2019157426A1 (https=)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112236412B (zh) * 2018-02-09 2024-01-30 维斯塔津治疗公司 4-氯代犬尿氨酸及中间体的合成
WO2022082100A1 (en) * 2020-10-16 2022-04-21 Vistagen Therapeutics, Inc. Cocrystals of l-4-chlorokynurenine, compositions and therapeutic uses thereof
CN118434750A (zh) * 2021-12-23 2024-08-02 新魁特株式会社 有机锌化合物以及有机锌化合物的制造方法
WO2023234187A1 (ja) * 2022-05-31 2023-12-07 シンクレスト株式会社 有機銅化合物の製造方法
US20240368190A1 (en) * 2023-04-14 2024-11-07 Revolution Medicines, Inc. Synthesis of ras inhibitors

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU643365B2 (en) 1991-02-28 1993-11-11 Aventisub Ii Inc. NMDA antagonists
US5484814A (en) 1991-02-28 1996-01-16 Merrell Dow Pharmaceuticals Inc. NMDA antagonists
GB9618349D0 (en) 1996-09-03 1996-10-16 Pharmacia Spa N-substituted 2-amino-4-phenyl-4-oxo-butanoic acid derivatives with kynurenine-3-hydroxylase inhibitory activity
JP2001517246A (ja) * 1997-06-23 2001-10-02 田辺製薬株式会社 α▲下４▼β▲下１▼媒介細胞接着の阻止剤
CN1309702C (zh) * 2005-10-28 2007-04-11 中国科学院上海有机化学研究所 犬尿氨酸酶的特异性抑制剂l－邻甲氧基苯甲酰基丙氨酸的合成方法
EP4385563A3 (en) 2013-01-22 2024-08-21 Vistagen Therapeutics, Inc. Dosage forms and therapeutic uses l-4-chlorokynurenine
US20160031800A1 (en) * 2013-03-14 2016-02-04 Vistagen Therapeutics, Inc. Synthesis of chiral kynurenine compounds and intermediates
CN107417558A (zh) * 2013-03-14 2017-12-01 维斯塔津治疗公司 用于合成手性犬尿氨酸化合物的方法
US9666192B2 (en) 2015-05-26 2017-05-30 Nuance Communications, Inc. Methods and apparatus for reducing latency in speech recognition applications
WO2017044516A1 (en) * 2015-09-08 2017-03-16 Cephalon, Inc. Prodrugs of chlorokynurenines
KR102021276B1 (ko) 2015-10-15 2019-09-16 엑손모빌 업스트림 리서치 캄파니 진폭 보존을 갖는 fwi 모델 도메인 각도 스택들
US20180305298A1 (en) * 2015-10-16 2018-10-25 Auspex Pharmaceuticals, Inc. Deuterated chlorokynurenines for the treatment of neuropsychiatric disorders
CN107129444B (zh) * 2016-02-29 2018-08-31 尚科生物医药（上海）有限公司 (s)-2-叔丁氧羰基氨基-3-(4-氨甲酰基-2,6-二甲基苯基)丙酸制备方法
CN112236412B (zh) * 2018-02-09 2024-01-30 维斯塔津治疗公司 4-氯代犬尿氨酸及中间体的合成

Also Published As

Publication number Publication date
WO2019157426A1 (en) 2019-08-15
JP7431163B2 (ja) 2024-02-14
EP3749638A1 (en) 2020-12-16
US20210276942A1 (en) 2021-09-09
CN118026866A (zh) 2024-05-14
EP3749638A4 (en) 2021-11-17
CN112236412A (zh) 2021-01-15
JP2021512926A (ja) 2021-05-20
CA3127220A1 (en) 2019-08-15
CN112236412B (zh) 2024-01-30
US11427530B2 (en) 2022-08-30
EP3749638B1 (en) 2023-04-05

Similar Documents

Publication Publication Date Title
CA3127220C (en) SYNTHESIS OF 4-CHLOROKYNURENINS AND INTERMEDIARIES
EP3581573B1 (en) Synthesis of a compound that modulates kinases
CA3101824C (en) Synthesis of peptide borate ester compound and use thereof
CA2860493C (en) Process for the asymmetric oxidation of organic compounds with peroxides in the presence of a chiral acid catalyst
KR20220158761A (ko) 사이클로스포린 유도체의 제조
EP4196481A1 (en) Process for preparing enantiomerically enriched jak inhibitors
JP2016520648A (ja) ｔｅｒｔ−ブチル ４−（（１Ｒ，２Ｓ，５Ｒ）−６−（ベンジルオキシ）−７−オキソ−１，６−ジアザビシクロ［３．２．１］オクタン−２−カルボキサミド）ピペリジン−１−カルボキシレートの調製
Sheehan et al. 4, 5-Diphenyl-4-oxazolin-2-one ring system as an amine protecting group
EP0297641B1 (fr) Composés guanidiniques comprenant un ion tétraphénylborate substitué, procédé d'obtention de ces composés et utilisation des composés lors de la synthése peptidique
KR920002530A (ko) 치환된 페닐아세틸렌 및 이를 포함하는 약제학적 조성물 및 이들의 제조방법
KR20240007121A (ko) Kit- 및 pdgfra-매개 질환을 치료하기 위한 화합물을 생산하기 위한 합성 방법 및 중간체
US20150246869A1 (en) Process for Preparing Cinacalcet and Pharmaceutically Acceptable Salts Thereof
SK13442000A3 (sk) Postup na prípravu tetrapeptidu
EP1611106B1 (en) Preparation of quinapril hydrochloride
JP7667998B2 (ja) アミド及びペプチドの製造方法
CN102471186B (zh) 制备芳基、杂芳基或烯基取代的不饱和烃类的方法
WO2026022282A1 (en) Processes for manufacturing biaryl thioethers
Fernández et al. Tuning the anionic cyclization-protonation of N-benzyl (diphenyl)-phosphinamides. Highly efficient synthesis of tetrahydrobenzo-1-aza-2λ5-phospholes containing a 1, 3-cyclohexadiene system
AU2023263648A1 (en) Method for preparing 4-[5-[bis(2-chloroethyl)amino]-1-methyl-1h-benzo[d]imidazol-2-yl]butyric acid alkyl esters and formylated derivatives
HK1048119A1 (en) Process for producing quinolonecarboxylic acids and intermediates thereof
EP4110759A1 (en) Process for the preparation of panobinostat
HK40018346B (en) Synthesis of a compound that modulates kinases
HUP0000420A2 (hu) Eljárás NMDA antagonisták előállítására
Albert et al. NH2 as a directing group: from the cyclopalladation of amino esters to the preparation of benzolactams by Pd (II)-catalyzed carbonylation of N-unprotected arylethylamines
JP2001131145A (ja) 光学活性３−アミノピロリジン誘導体の製造法

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20240212

Q17 Modified document published

Free format text: ST27 STATUS EVENT CODE: A-4-4-Q10-Q17-Q103 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: DOCUMENT PUBLISHED

Effective date: 20241114

F11 Ip right granted following substantive examination

Free format text: ST27 STATUS EVENT CODE: A-4-4-F10-F11-X000 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: GRANT BY ISSUANCE

Effective date: 20241119

MPN Maintenance fee for patent paid

Free format text: FEE DESCRIPTION TEXT: MF (PATENT, 6TH ANNIV.) - STANDARD

Year of fee payment: 6

U00 Fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U00-U101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE REQUEST RECEIVED

Effective date: 20250207

U11 Full renewal or maintenance fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT DETERMINED COMPLIANT

Effective date: 20250207

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT PAID IN FULL

Effective date: 20250207

MPN Maintenance fee for patent paid

Free format text: FEE DESCRIPTION TEXT: MF (PATENT, 7TH ANNIV.) - STANDARD

Year of fee payment: 7

U00 Fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U00-U101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE REQUEST RECEIVED

Effective date: 20260213

U11 Full renewal or maintenance fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT PAID IN FULL

Effective date: 20260213

W00 Other event occurred

Free format text: ST27 STATUS EVENT CODE: A-4-4-W10-W00-W100 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: LETTER SENT

Effective date: 20260325