CA3025406C - Tetradentate chelating monoquinoline derivative, manufacturing method thereof, and application of same as metal ion regulator for neurodegenerative disease - Google Patents

Tetradentate chelating monoquinoline derivative, manufacturing method thereof, and application of same as metal ion regulator for neurodegenerative disease Download PDF

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Publication number
CA3025406C
CA3025406C CA3025406A CA3025406A CA3025406C CA 3025406 C CA3025406 C CA 3025406C CA 3025406 A CA3025406 A CA 3025406A CA 3025406 A CA3025406 A CA 3025406A CA 3025406 C CA3025406 C CA 3025406C
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Prior art keywords
disease
derivative
tetradentate chelating
composition
copper
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CA3025406A
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French (fr)
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CA3025406A1 (en
Inventor
Yan Liu
Weixin Zhang
Daya HUANG
Meijie HUANG
Dean Wang
Ju HUANG
Siwei SHU
Michel NGUYEN
Anne Robert
Bernard Meunier
Xingguo LIU
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Guangdong University of Technology
Centre National de la Recherche Scientifique CNRS
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Guangdong University of Technology
Centre National de la Recherche Scientifique CNRS
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D215/38—Nitrogen atoms
    • C07D215/40—Nitrogen atoms attached in position 8
    • 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P39/00—General protective or antinoxious agents
    • A61P39/04—Chelating agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P39/00—General protective or antinoxious agents
    • A61P39/06—Free radical scavengers or antioxidants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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
    • C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
    • C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
    • 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
    • C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
    • 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

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Epidemiology (AREA)
  • Psychology (AREA)
  • Toxicology (AREA)
  • Psychiatry (AREA)
  • Hospice & Palliative Care (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Biochemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Quinoline Compounds (AREA)

Abstract

ABSTRACT
A tetradentate chelating monoquinoline derivative with a structure as shown in formula (I) is able to specifically chelate redox active metal ions like copper ions that are dis-regulated in neurodegenerative diseases (Alzheimer's disease, Huntington's disease, Parkinson's disease, and amyotrophic lateral sclerosis), or copper accumulation disease like Wilson's disease. The binding constants of these derivatives for zinc are 6-10 orders of magnitude below that ones for copper, and these derivatives have a good capability of reducing an oxidative stress. The method for preparing the derivative is simple and the derivatives have good application prospects in manufacturing drugs for neurodegenerative diseases and diseases related to disorder of copper metabolism.

X formula (I) Date Recue/Date Received 2020-05-13

Description

TETRADENTATE CHELATING MONOQUINOLINE
DERIVATIVE, MANUFACTURING METHOD THEREOF, AND APPLICATION OF SAME AS METAL ION

Claims (8)

We claim:
1. A tetradentate chelating monoquinoline derivative, wherein a structure of the derivative is as shown in formula (I):

Ri X
formula (I);
X represents an ¨NH2;
Y represents a group with the following fommla:
¨(C112)n¨NR6¨(C112).¨NR7%; n represents 1 or 2, m represents 2 or 3;
R6 represents hydrogen atom, C1_6 alkyl, C3-6 cycloalkyl, CF3 or a halogen atom;
the definition of R7 or R8 is the same as that of R6;
Ri, R2, R3, R4 and R5 are the same or different and independently represent a group or an atom selected from the group consisting of H, a halogen atom, and -CF 3 .
2. A use of the tetradentate chelating monoquinoline derivative of claim 1 for the complexation of metal ions.
3. The use of claim 2, wherein the monoquinoline derivative is able to specifically chelate redox active metal ions, wherein the metal ions are copper ions.
4. A composition comprising the tetradentate chelating monoquinoline derivative of claim 1 and a pharmaceutically acceptable excipient for use in the manufacture of a medicament.
5. The composition of claim 4, wherein the tetradentate chelating monoquinoline derivative is a pharmaceutically acceptable salt thereof.
6. The composition of claim 4 or 5, wherein the medicament is for treating a neurodegenerative disease.
Date Recue/Date Received 2020-12-11
7. The composition of claim 6, wherein the neurodegenerative disease is Alzheimer's disease, Huntington's disease, Parkinson's disease, Down syndrome, or amyotrophic lateral sclerosis.
8. The composition of claim 4 or 5, wherein the medicament is for treating Wilson's disease.

Date Recue/Date Received 2020-12-11
CA3025406A 2016-05-27 2017-05-25 Tetradentate chelating monoquinoline derivative, manufacturing method thereof, and application of same as metal ion regulator for neurodegenerative disease Active CA3025406C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CN201610369550.XA CN105949120B (en) 2016-05-27 2016-05-27 A kind of application of four teeth chelating type list quinoline and preparation method thereof and metal ion control agent as neurodegenerative disease
CN201610369550.X 2016-05-27
PCT/CN2017/085886 WO2017202360A1 (en) 2016-05-27 2017-05-25 Tetradentate chelating monoquinoline derivative, manufacturing method thereof, and application of same as metal ion regulator for neurodegenerative disease

Publications (2)

Publication Number Publication Date
CA3025406A1 CA3025406A1 (en) 2017-11-30
CA3025406C true CA3025406C (en) 2021-06-01

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US (1) US10807957B2 (en)
EP (1) EP3466931B1 (en)
JP (1) JP6889825B2 (en)
CN (1) CN105949120B (en)
CA (1) CA3025406C (en)
ES (1) ES2974620T3 (en)
HR (1) HRP20240476T1 (en)
HU (1) HUE066677T2 (en)
WO (1) WO2017202360A1 (en)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105949120B (en) 2016-05-27 2018-07-24 广东工业大学 A kind of application of four teeth chelating type list quinoline and preparation method thereof and metal ion control agent as neurodegenerative disease
CN107987016B (en) * 2016-10-27 2022-05-27 广州威尔曼新药研发有限公司 Crystal of compound N-butyl-2, 2' -imino-bis (8-quinolinamine), pharmaceutical composition and application thereof
CN106674102A (en) * 2016-12-26 2017-05-17 广东工业大学 Halogenated quinoline compound and preparation method thereof
US12215128B2 (en) * 2018-07-20 2025-02-04 Cold Spring Harbor Laboratory (Pyridinylmethyl)butanediamine derivatives that chelate copper
CN113318116B (en) * 2021-06-17 2023-08-25 成都奥睿药业有限公司 Use of curcumin difluoro boron and its derivative
WO2025081478A1 (en) * 2023-10-20 2025-04-24 Guangdong University Of Technology Specific tetradentate copper chelators for the treatment of wilson's disease
CN117427075A (en) * 2023-12-01 2024-01-23 广东工业大学 Application of TDMQ20 in the preparation of drugs that inhibit LPS-induced neuroinflammation
CN118946358A (en) 2024-03-15 2024-11-12 广东工业大学 Specific tetradentate copper chelators as anticancer agents

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE466534B (en) * 1988-12-30 1992-03-02 Exploaterings Ab Tbf ADSORPTIONS FOR METAL IONS, PROTEINS AND OTHER INORGANIC AND ORGANIC SUBSTANCES
FR2724171B1 (en) * 1994-09-05 1997-01-03 Synthelabo DERIVATIVES OF 3.3A, 4,5-TETRAHYDRO-1H-OXAZOLO (3,4-A) QUINOLEIN-1-ONE, THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATION
US6277841B1 (en) * 2000-03-02 2001-08-21 Mallinckrodt Inc. Quinoline ligands and metal complexes for diagnosis and therapy
US7589209B2 (en) * 2004-03-23 2009-09-15 New York University 8-hydroxyquinoline tripodal metal ion probes
US20060094755A1 (en) * 2004-10-28 2006-05-04 Bioflexis, Llc Novel quinoline-based metal chelators as antiviral agents
FR2984317B1 (en) * 2011-12-20 2015-02-27 Univ Rennes METAL CHELATING COMPOUNDS HAVING AT LEAST ONE POLYAMINATED CHAIN.
RU2642466C2 (en) * 2013-04-02 2018-01-25 Аннцзи Фармасьютикал Ко., Лтд. Multifunctional quinoline derivatives as antineurodegenerative agents
GB201403595D0 (en) * 2014-02-28 2014-04-16 Isis Innovation Quinoline compounds
CN105949120B (en) * 2016-05-27 2018-07-24 广东工业大学 A kind of application of four teeth chelating type list quinoline and preparation method thereof and metal ion control agent as neurodegenerative disease

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WO2017202360A1 (en) 2017-11-30
HUE066677T2 (en) 2024-08-28
HRP20240476T1 (en) 2024-08-30
US20190092730A1 (en) 2019-03-28
EP3466931B1 (en) 2024-01-10
JP6889825B2 (en) 2021-06-18
EP3466931A1 (en) 2019-04-10
JP2019516776A (en) 2019-06-20
CA3025406A1 (en) 2017-11-30
CN105949120A (en) 2016-09-21
EP3466931A4 (en) 2019-11-27
EP3466931C0 (en) 2024-01-10
ES2974620T3 (en) 2024-06-28
CN105949120B (en) 2018-07-24
US10807957B2 (en) 2020-10-20

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