CN114364658A - 一种左旋吡喹酮及其手性中间体的制备方法和组合物 - Google Patents

一种左旋吡喹酮及其手性中间体的制备方法和组合物 Download PDF

Info

Publication number
CN114364658A
CN114364658A CN202080007560.3A CN202080007560A CN114364658A CN 114364658 A CN114364658 A CN 114364658A CN 202080007560 A CN202080007560 A CN 202080007560A CN 114364658 A CN114364658 A CN 114364658A
Authority
CN
China
Prior art keywords
tetrahydroisoquinoline
carboxylic acid
high performance
performance liquid
mobile phase
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.)
Pending
Application number
CN202080007560.3A
Other languages
English (en)
Inventor
钱明心
汤灵娇
居述云
吴坚平
杨立荣
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Tongli Biomedical Co ltd
Zhejiang University ZJU
Original Assignee
Tongli Biomedical Co ltd
Zhejiang University ZJU
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 Tongli Biomedical Co ltd, Zhejiang University ZJU filed Critical Tongli Biomedical Co ltd
Publication of CN114364658A publication Critical patent/CN114364658A/zh
Pending legal-status Critical Current

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
    • C07D217/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/10—Anthelmintics
    • A61P33/12—Schistosomicides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
    • C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
    • C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
    • C07D217/16—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
    • G01N30/02—Column chromatography
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Analytical Chemistry (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Pathology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Immunology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Physics & Mathematics (AREA)
  • Biochemistry (AREA)
  • Physics & Mathematics (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

一种制备和检测1,2,3,4‑四氢异喹啉‑1‑甲酸的(R)或(S)构型及其组合物的方法并用于制备左旋吡喹酮及其关键中间体。其中以1,2,3,4‑四氢异喹啉‑1‑甲酸酯的外消旋体为底物制备(R)或(S)酸，并通过高效液相色谱检测反应体系中(R)或(S)‑1,2,3,4‑四氢异喹啉‑1‑甲酸酯、(R)或(S)‑1,2,3,4‑四氢异喹啉‑1‑甲酸的含量；由上述方法制备的包括四种构型的组合物、左旋吡喹酮的关键中间体和左旋吡喹酮；上述方法能够从始至终实时监测反应体系进行的程度，以达到四种构型及含量的检测，确保目的产物手性纯度的质量控制，能够满足产品大规模产业化中手性分析的需求。

Description

PCT国内申请，说明书已公开。

Claims (21)

  1. PCT国内申请，权利要求书已公开。
CN202080007560.3A 2019-09-11 2020-09-10 一种左旋吡喹酮及其手性中间体的制备方法和组合物 Pending CN114364658A (zh)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CN201910856165.1A CN112480001A (zh) 2019-09-11 2019-09-11 一种制备左旋吡喹酮手性中间体的方法及组合物
CN2019108561651 2019-09-11
PCT/CN2020/114335 WO2021047565A1 (zh) 2019-09-11 2020-09-10 一种左旋吡喹酮及其手性中间体的制备方法和组合物

Publications (1)

Publication Number Publication Date
CN114364658A true CN114364658A (zh) 2022-04-15

Family

ID=74867247

Family Applications (2)

Application Number Title Priority Date Filing Date
CN201910856165.1A Pending CN112480001A (zh) 2019-09-11 2019-09-11 一种制备左旋吡喹酮手性中间体的方法及组合物
CN202080007560.3A Pending CN114364658A (zh) 2019-09-11 2020-09-10 一种左旋吡喹酮及其手性中间体的制备方法和组合物

Family Applications Before (1)

Application Number Title Priority Date Filing Date
CN201910856165.1A Pending CN112480001A (zh) 2019-09-11 2019-09-11 一种制备左旋吡喹酮手性中间体的方法及组合物

Country Status (2)

Country Link
CN (2) CN112480001A (zh)
WO (1) WO2021047565A1 (zh)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116183741B (zh) * 2022-12-03 2023-08-29 华夏生生药业(北京)有限公司 一种氟康唑中氯乙酰氯的检测方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103333930A (zh) * 2012-02-28 2013-10-02 苏州同力生物医药有限公司 合成左旋吡喹酮的方法
CN104557911A (zh) * 2013-10-17 2015-04-29 苏州同力生物医药有限公司 一种左旋吡喹酮的制备方法
CN108794466A (zh) * 2017-04-26 2018-11-13 苏州同力生物医药有限公司 一种无定形左旋吡喹酮固体及其制备方法和应用
CN109971802A (zh) * 2017-12-28 2019-07-05 苏州同力生物医药有限公司 一种酶法拆分制备(s)-1,2,3,4-四氢异喹啉-1-甲酸及其衍生物的方法

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103333930A (zh) * 2012-02-28 2013-10-02 苏州同力生物医药有限公司 合成左旋吡喹酮的方法
CN104557911A (zh) * 2013-10-17 2015-04-29 苏州同力生物医药有限公司 一种左旋吡喹酮的制备方法
CN108794466A (zh) * 2017-04-26 2018-11-13 苏州同力生物医药有限公司 一种无定形左旋吡喹酮固体及其制备方法和应用
CN109971802A (zh) * 2017-12-28 2019-07-05 苏州同力生物医药有限公司 一种酶法拆分制备(s)-1,2,3,4-四氢异喹啉-1-甲酸及其衍生物的方法

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
ISTVÁN ILISZ 等: "Direct high-performance liquid chromatographic antioseparation of secondary amino acids on Cinchona alkaloid-based chiral zwitterionic stationary phases. Unusual temperature behavior", 《JOURNAL OF CHROMATOGRAPHY A》 *
PAÁL TIHAMÉR A.等: "Directed (R)- or (S)-Selective Dynamic Kinetic Enzymatic Hydrolysis of 1,2,3,4-Tetrahydroisoquinoline-1-carboxylic Esters", 《EUR. J. ORG. CHEM.》 *

Also Published As

Publication number Publication date
WO2021047565A1 (zh) 2021-03-18
CN112480001A (zh) 2021-03-12

Similar Documents

Publication Publication Date Title
CN108283000A (zh) γ-羟基丁酸的前药及其组合物和用途
US20080287680A1 (en) Solifenacin Succinate-Containing Composition
AU2014336747B2 (en) Crystal form of (r)-praziquantel and preparation method and application thereof
CN108689905B (zh) 一种维格列汀杂质化合物及其制备方法、检测方法和用途
CN104557911B (zh) 一种左旋吡喹酮的制备方法
WO2013127356A1 (zh) 左旋吡喹酮的合成方法
CA2560080A1 (en) Solifenacin-containing composition
CN114364658A (zh) 一种左旋吡喹酮及其手性中间体的制备方法和组合物
WO2013174207A1 (zh) 一种蛋白质络氨酸磷酸酶抑制剂、其制备方法及其用途
JP6422871B2 (ja) ピロール誘導体の製造方法及びその中間体
CN105693605B (zh) 一种光学纯(r)/(s)‑氯喹的不对称合成方法
WO2021047566A1 (zh) 一种(r)-1,2,3,4-四氢异喹啉-1-羧酸及其衍生物和左旋吡喹酮的制备方法
EP4310080A1 (en) Polymorphic forms of compound and preparation method therefor and application thereof
CN109180606B (zh) 一类具有光学活性的β-氨基酮的合成方法
CN108912018B (zh) 一种用于合成舒必利的关键中间体中杂质化合物的制备方法及其用途
UA105424C2 (uk) Агомелатину гідроброміду гідрат і його отримання
Nodzewska et al. Solvent-free synthesis of a secondary N-benzhydrylamine as a chiral reagent for asymmetric deprotonation of bicyclic N-benzylamino ketones
KR100933172B1 (ko) 아토르바스타틴 칼슘염의 개선된 제조방법
CN110128500A (zh) 制备α-酰胺基酰胺类物质的Ugi混合溶剂法
US10221185B2 (en) Crystal form of substituted aminopyran derivativek
US20220227766A1 (en) Preparation method for (r)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid, derivatives thereof and levo-praziquantel
CN107174586B (zh) 以芦竹碱衍生物为活性成分的药物组合物及其应用
CN112250658B (zh) 一种甲酰化双环醇及其制备方法
CN109384716A (zh) 一种氘代喹啉化合物及其制备和用途
CN108732276B (zh) 马昔腾坦有关物质的高效液相色谱分析方法

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination