WO2000025767A3 - Use of triphenylbutene derivatives for the treatment of neurological disorders - Google Patents

Use of triphenylbutene derivatives for the treatment of neurological disorders Download PDF

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Publication number
WO2000025767A3
WO2000025767A3 PCT/GB1999/003583 GB9903583W WO0025767A3 WO 2000025767 A3 WO2000025767 A3 WO 2000025767A3 GB 9903583 W GB9903583 W GB 9903583W WO 0025767 A3 WO0025767 A3 WO 0025767A3
Authority
WO
WIPO (PCT)
Prior art keywords
formula
hydrogen
4alkoxy
4alkyl
halo
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.)
Ceased
Application number
PCT/GB1999/003583
Other languages
French (fr)
Other versions
WO2000025767A2 (en
Inventor
Richard Alan Keith
Timothy Martin Piser
Michael Thaddeus Klimas
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.)
AstraZeneca AB
Original Assignee
AstraZeneca AB
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 AstraZeneca AB filed Critical AstraZeneca AB
Priority to EP99954098A priority Critical patent/EP1127045B1/en
Priority to DE69933885T priority patent/DE69933885T2/en
Priority to JP2000579208A priority patent/JP2002528489A/en
Priority to AU10542/00A priority patent/AU1054200A/en
Priority to US09/831,211 priority patent/US6489481B1/en
Publication of WO2000025767A2 publication Critical patent/WO2000025767A2/en
Publication of WO2000025767A3 publication Critical patent/WO2000025767A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • 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
    • A61K31/13—Amines
    • A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
    • A61K31/138—Aryloxyalkylamines, e.g. propranolol, tamoxifen, phenoxybenzamine
    • 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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A61K31/222—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin with compounds having aromatic groups, e.g. dipivefrine, ibopamine
    • 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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A61K31/223—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of alpha-aminoacids
    • 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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
    • A61K31/24—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group having an amino or nitro group
    • 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
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • 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
    • A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • 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
    • A61P25/28—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

Landscapes

  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychiatry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Saccharide Compounds (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Pyridine Compounds (AREA)
  • Pyrrole Compounds (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

The use of a compound of Formula (VIII) in the manufacture of a medicament for the treatment of or the prevention of neurological disorders, in a warm-blooded mammal, wherein A and B are selected from: Formula (IX) or Formula (X) such that when A is of Formula (X) then B is of Formula (IX) and when A is of Formula (IX) then B is of Formula (X). R1 is selected from hydrogen, halo, aryl, carbamoyl, <U>N</U>-C1-4alkylcarbamoyl or <U>NN</U>-di-C1-4alkylcarbamoyl; D is selected from C1-4alkylene, C1-4alkenylene or alkynylene; R2 is selected from hydrogen, C1-4alkyl or hydroxy; R3 is selected from hydrogen, hydroxy, halo, PO4, C1-4alkoxy, or a group of the formula: -E-F-G-H wherein: E is selected from: (a), (b), (c), (d), (e), or (f); F is selected from: (a), (b), or a direct bond; G is selected from C1-6alkyl, or a direct bond; H is selected from hydrogen, C1-4alkoxy, or optionally substituted aryl; heteroaryl, or carbocyclyl; R4 and R5 are independently selected from methyl, ethyl or phenyl, or together with the nitrogen atom to which they are attached form a ring selected from pyrrolidine, piperidine or morpholine; R6 is selected from hydrogen, C1-4alkyl; C1-4alkoxy, halo, or a ring fused phenyl group fused via carbons 3 and 4 on the phenyl group of Formula (X); R7 and R8 are either both hydrogen or when A is of Formula (X) may be joined either via a sulphur atom, via -CH2- or via -C2H4; R9 is selected from hydrogen or C1-4alkyl; and n is 2 or 3; or a pharmaceutically acceptable salt, prodrug or solvate thereof. Processes for their preparation of compounds of Formula (VIII) are described, as are compositions containing them and their use.
PCT/GB1999/003583 1998-11-04 1999-10-29 Use of triphenylbutene derivatives for the treatment of neurological disorders Ceased WO2000025767A2 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
EP99954098A EP1127045B1 (en) 1998-11-04 1999-10-29 Triphenylbutene derivatives for the treatment of neurological disorders
DE69933885T DE69933885T2 (en) 1998-11-04 1999-10-29 TRIPHENYLBUTEN DERIVATIVES FOR THE TREATMENT OF NEUROLOGICAL DISORDERS
JP2000579208A JP2002528489A (en) 1998-11-04 1999-10-29 Nervous system disorders
AU10542/00A AU1054200A (en) 1998-11-04 1999-10-29 Neurological disorders
US09/831,211 US6489481B1 (en) 1998-11-04 1999-10-29 Method for treating neurological disorders

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9824207.6 1998-11-04
GBGB9824207.6A GB9824207D0 (en) 1998-11-04 1998-11-04 Neurological disorders

Publications (2)

Publication Number Publication Date
WO2000025767A2 WO2000025767A2 (en) 2000-05-11
WO2000025767A3 true WO2000025767A3 (en) 2000-09-28

Family

ID=10841850

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1999/003583 Ceased WO2000025767A2 (en) 1998-11-04 1999-10-29 Use of triphenylbutene derivatives for the treatment of neurological disorders

Country Status (9)

Country Link
US (1) US6489481B1 (en)
EP (1) EP1127045B1 (en)
JP (1) JP2002528489A (en)
AT (1) ATE344230T1 (en)
AU (1) AU1054200A (en)
DE (1) DE69933885T2 (en)
ES (1) ES2274645T3 (en)
GB (1) GB9824207D0 (en)
WO (1) WO2000025767A2 (en)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7710744B2 (en) * 2004-10-11 2010-05-04 Stmicroelectronics S.R.L. Method for controlling a full bridge converter with a current-doubler
US20100048713A1 (en) * 2006-01-06 2010-02-25 Aarhus Universitet Compounds acting on the serotonin transporter
US8062588B2 (en) * 2006-03-22 2011-11-22 Zimek Technologies Ip, Llc Ultrasonic sanitation device and associated methods
JP5382633B2 (en) * 2006-05-25 2014-01-08 学校法人順正学園 Preventive or therapeutic agent for cerebrovascular dementia
US20090291134A1 (en) * 2006-11-21 2009-11-26 Jina Pharmaceuticals, Inc. Endoxifen methods and compositions in the treatment of psychiatric and neurodegenerative diseases
JP7325104B2 (en) * 2016-07-27 2023-08-14 ケース ウェスタン リザーブ ユニバーシティ Compounds and methods for promoting myelination
US11541033B2 (en) 2017-06-02 2023-01-03 Fujifilm Toyama Chemical Co., Ltd. Agent for preventing or treating Alzheimer's disease
RU2728717C1 (en) 2017-06-02 2020-07-30 ФУДЖИФИЛМ Тояма Кемикал Ко., Лтд. Agent for preventing or treating spinal carbellar ataxia
JP7282028B2 (en) 2017-06-02 2023-05-26 富士フイルム富山化学株式会社 Cerebral atrophy preventive or therapeutic agent
KR20200003102A (en) 2017-06-02 2020-01-08 후지필름 도야마 케미컬 가부시키가이샤 Amyloid β Protein Amount Reducing Agent
CN109293519B (en) * 2017-07-25 2021-09-28 北京斯利安药业有限公司 Preparation method of tamoxifen citrate crystal form A
JP7227914B2 (en) * 2017-10-30 2023-02-22 富士フイルム富山化学株式会社 Emopamil-binding protein binding agent and its use
WO2019103989A1 (en) * 2017-11-22 2019-05-31 Temple University-Of The Commonwealth System Of Higher Education Novel functionalized n,n-dialkylamino phenyl ethers and their method of use
CN116969983A (en) * 2018-09-12 2023-10-31 路易斯安那泽维尔大学 estrogen receptor targeting antagonist

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE637389A (en) * 1962-09-13
US3288806A (en) * 1964-03-23 1966-11-29 Parke Davis & Co Alpha-(aminoethoxyphenyl)-alpha-alkylstilbenes
EP0011372A1 (en) * 1978-11-07 1980-05-28 Imperial Chemical Industries Plc 1-Acyloxyphenyl-1,2-diphenylalkene derivatives, processes for their manufacture and a pharmaceutical composition containing these derivatives
US4623660A (en) * 1977-08-22 1986-11-18 Imperial Chemical Industries Plc Triphenylalkene derivatives
DE4320896A1 (en) * 1993-06-24 1995-01-05 Denecke Rainer Dr Med Vet Product for the therapy and prophylaxis of dementias
WO1996040098A2 (en) * 1995-06-07 1996-12-19 Neorx Corporation Prevention and treatment of cardiovascular pathologies with tamoxifen analogues
EP0792638A1 (en) * 1996-02-28 1997-09-03 Pfizer Inc. Use of 1,1,2-triphenylbut-1-ene derivatives for the manufacture of a medicament for treating Alzheimer's disease
EP0797990A2 (en) * 1993-04-10 1997-10-01 Altramed Holdings Ltd. Use of steroid antagonists for the treatment and prophylaxis of dementia-related disorders
WO1998048784A2 (en) * 1997-04-28 1998-11-05 The University Of British Columbia Method and composition for modulating amyloidosis
WO1999008682A1 (en) * 1997-08-15 1999-02-25 Duke University A method of preventing or treating estrogen-dependent diseases and disorders
EP0976404A2 (en) * 1998-07-30 2000-02-02 Pfizer Products Inc. A pharmaceutical composition for the prevention and treatment of diseases of cognitive dysfunction in a mammal

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE637389A (en) * 1962-09-13
US3288806A (en) * 1964-03-23 1966-11-29 Parke Davis & Co Alpha-(aminoethoxyphenyl)-alpha-alkylstilbenes
US4623660A (en) * 1977-08-22 1986-11-18 Imperial Chemical Industries Plc Triphenylalkene derivatives
EP0011372A1 (en) * 1978-11-07 1980-05-28 Imperial Chemical Industries Plc 1-Acyloxyphenyl-1,2-diphenylalkene derivatives, processes for their manufacture and a pharmaceutical composition containing these derivatives
EP0797990A2 (en) * 1993-04-10 1997-10-01 Altramed Holdings Ltd. Use of steroid antagonists for the treatment and prophylaxis of dementia-related disorders
DE4320896A1 (en) * 1993-06-24 1995-01-05 Denecke Rainer Dr Med Vet Product for the therapy and prophylaxis of dementias
WO1996040098A2 (en) * 1995-06-07 1996-12-19 Neorx Corporation Prevention and treatment of cardiovascular pathologies with tamoxifen analogues
EP0792638A1 (en) * 1996-02-28 1997-09-03 Pfizer Inc. Use of 1,1,2-triphenylbut-1-ene derivatives for the manufacture of a medicament for treating Alzheimer's disease
WO1998048784A2 (en) * 1997-04-28 1998-11-05 The University Of British Columbia Method and composition for modulating amyloidosis
WO1999008682A1 (en) * 1997-08-15 1999-02-25 Duke University A method of preventing or treating estrogen-dependent diseases and disorders
EP0976404A2 (en) * 1998-07-30 2000-02-02 Pfizer Products Inc. A pharmaceutical composition for the prevention and treatment of diseases of cognitive dysfunction in a mammal

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
WATTS, COLIN K. W. ET AL: "Microsomal binding sites for nonsteroidal antiestrogens in MCF 7 human mammary carcinoma cells. Demonstration of high affinity and narrow specificity for basic ether derivatives of triphenylethylene", J. BIOL. CHEM. (1984), 259(7), 4223-9, XP000913401 *

Also Published As

Publication number Publication date
DE69933885D1 (en) 2006-12-14
US6489481B1 (en) 2002-12-03
EP1127045A2 (en) 2001-08-29
AU1054200A (en) 2000-05-22
ES2274645T3 (en) 2007-05-16
ATE344230T1 (en) 2006-11-15
WO2000025767A2 (en) 2000-05-11
JP2002528489A (en) 2002-09-03
GB9824207D0 (en) 1998-12-30
EP1127045B1 (en) 2006-11-02
DE69933885T2 (en) 2007-05-24

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