CN118026866A - 4-氯代犬尿氨酸及中间体的合成 - Google Patents

4-氯代犬尿氨酸及中间体的合成 Download PDF

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Publication number
CN118026866A
CN118026866A CN202410094204.XA CN202410094204A CN118026866A CN 118026866 A CN118026866 A CN 118026866A CN 202410094204 A CN202410094204 A CN 202410094204A CN 118026866 A CN118026866 A CN 118026866A
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CN
China
Prior art keywords
reactor
minutes
chlorokynurenine
compound
free acid
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Pending
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CN202410094204.XA
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English (en)
Chinese (zh)
Inventor
D·莱温
P·利明
E·艾森莱希
X·K·刘
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Vistagen Therapeutics Inc
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Vistagen Therapeutics Inc
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Publication of CN118026866A publication Critical patent/CN118026866A/zh
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    • 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

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  • 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)
CN202410094204.XA 2018-02-09 2019-02-11 4-氯代犬尿氨酸及中间体的合成 Pending CN118026866A (zh)

Applications Claiming Priority (4)

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
CN201980021535.8A CN112236412B (zh) 2018-02-09 2019-02-11 4-氯代犬尿氨酸及中间体的合成

Related Parent Applications (1)

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CN201980021535.8A Division CN112236412B (zh) 2018-02-09 2019-02-11 4-氯代犬尿氨酸及中间体的合成

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CN118026866A true CN118026866A (zh) 2024-05-14

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CN201980021535.8A Active CN112236412B (zh) 2018-02-09 2019-02-11 4-氯代犬尿氨酸及中间体的合成

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US (1) US11427530B2 (https=)
EP (1) EP3749638B1 (https=)
JP (1) JP7431163B2 (https=)
CN (2) CN118026866A (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
CN118026866A (zh) * 2018-02-09 2024-05-14 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
CA3241944A1 (en) * 2021-12-23 2023-06-29 Syncrest Inc. Organic zinc compound and production method for organic zinc compound
US20250326774A1 (en) * 2022-05-31 2025-10-23 Syncrest Inc. Method for producing organic copper compound
EP4695233A2 (en) * 2023-04-14 2026-02-18 Revolution Medicines, Inc. Synthesis of ras inhibitors

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017044516A1 (en) * 2015-09-08 2017-03-16 Cephalon, Inc. Prodrugs of chlorokynurenines
WO2017065899A1 (en) * 2015-10-16 2017-04-20 Auspex Pharmaceuticals, Inc. Deuterated chlorokynurenines for the treatment of neuropsychiatric disorders
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

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US5484814A (en) 1991-02-28 1996-01-16 Merrell Dow Pharmaceuticals Inc. NMDA antagonists
DK0501378T3 (da) 1991-02-28 1995-03-20 Merrell Dow Pharma NMDA-antagonister
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
AU8163398A (en) * 1997-06-23 1999-01-04 Pharmacia & Upjohn Company Inhibitors of alpha4beta1mediated cell adhesion
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
PT3598971T (pt) 2013-01-22 2024-06-20 Vistagen Therapeutics Inc ¿formas de dosagem e utilizações terapêuticas de l-4 cloroquinurenina
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
WO2014152835A1 (en) * 2013-03-14 2014-09-25 Vistagen Therapeutics, Inc. Synthesis of chiral kynurenine compounds and intermediates
US9666192B2 (en) 2015-05-26 2017-05-30 Nuance Communications, Inc. Methods and apparatus for reducing latency in speech recognition applications
US10520619B2 (en) 2015-10-15 2019-12-31 Exxonmobil Upstream Research Company FWI model domain angle stacks with amplitude preservation
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

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017044516A1 (en) * 2015-09-08 2017-03-16 Cephalon, Inc. Prodrugs of chlorokynurenines
WO2017065899A1 (en) * 2015-10-16 2017-04-20 Auspex Pharmaceuticals, Inc. Deuterated chlorokynurenines for the treatment of neuropsychiatric disorders
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

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US11427530B2 (en) 2022-08-30
EP3749638B1 (en) 2023-04-05
US20210276942A1 (en) 2021-09-09
JP2021512926A (ja) 2021-05-20
EP3749638A1 (en) 2020-12-16
CA3127220A1 (en) 2019-08-15
CN112236412B (zh) 2024-01-30
EP3749638A4 (en) 2021-11-17
WO2019157426A1 (en) 2019-08-15
CN112236412A (zh) 2021-01-15
CA3127220C (en) 2024-11-19
JP7431163B2 (ja) 2024-02-14

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