WO2004047756A3 - Propargyl-trifluoromethoxy-amino-benzothiazole derivatives - Google Patents

Propargyl-trifluoromethoxy-amino-benzothiazole derivatives Download PDF

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Publication number
WO2004047756A3
WO2004047756A3 PCT/US2003/037592 US0337592W WO2004047756A3 WO 2004047756 A3 WO2004047756 A3 WO 2004047756A3 US 0337592 W US0337592 W US 0337592W WO 2004047756 A3 WO2004047756 A3 WO 2004047756A3
Authority
WO
WIPO (PCT)
Prior art keywords
present
integer
alkyl
propargyl
trifluoromethoxy
Prior art date
Application number
PCT/US2003/037592
Other languages
French (fr)
Other versions
WO2004047756A2 (en
Inventor
Jeffrey Sterling
Liat Hayardeny
Eliezer Flab
Yaacov Herzig
David Lerner
Original Assignee
Teva Pharma
Teva Pharmaceutical Usa 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 Teva Pharma, Teva Pharmaceutical Usa Inc filed Critical Teva Pharma
Priority to BR0315704-0A priority Critical patent/BR0315704A/en
Priority to CA002507414A priority patent/CA2507414A1/en
Priority to EP03787112A priority patent/EP1569641A2/en
Priority to JP2004555702A priority patent/JP2006507350A/en
Priority to AU2003295898A priority patent/AU2003295898A1/en
Priority to MXPA05005414A priority patent/MXPA05005414A/en
Publication of WO2004047756A2 publication Critical patent/WO2004047756A2/en
Publication of WO2004047756A3 publication Critical patent/WO2004047756A3/en
Priority to NO20052979A priority patent/NO20052979L/en
Priority to IS7906A priority patent/IS7906A/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/425—Thiazoles
    • A61K31/428—Thiazoles condensed with carbocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • 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
    • A61P25/14—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
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • 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
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/06—Antiglaucoma agents or miotics
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/68—Benzothiazoles 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 in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/68—Benzothiazoles 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 in position 2
    • C07D277/82—Nitrogen atoms

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Psychiatry (AREA)
  • Ophthalmology & Optometry (AREA)
  • Psychology (AREA)
  • Urology & Nephrology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Hospice & Palliative Care (AREA)
  • Dermatology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Vascular Medicine (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

The subject invention provides compounds having the structure (I): wherein R1 is present or absent, and when present is H, C1-C6alkyl, C1-C6 alkynyl, - (CH2)yS (CH2 )xCH3, C1-C6 aminoalkyl, C1-C6 hydroxyalkyl or -(CH2)nC(=0) (C6H4) (CH2)R2; R2 is H or C1-C4 alkyl; R3 is H or C1-C4 alkyl; R4 is present or absent, and when present is H, C1-C6 alkyl, C1-C6 alkynyl, - (CH2) yS (CH2) xCH3 , C1-C6 aminoalkyl, C1-C6 hydroxyalkyl or -(CH2) nC (=O) (C6H4) (CH2) R2; wherein n is an integer from 1-6; wherein x is 0 or an integer from 1-5 and y is an integer from 1-5, such that x+y<6; at least one of R1 or R4 is present; the dashed line represents a bond between one of the nitrogen atoms and the intervening carbon atom; and any compound is charged when both R1 and R4 are present, or any specific enantiomer thereof or any pharmaceutically acceptable salt thereof, and a method for treating a neurologic disorder or multiple sclerosis by administering a therapeutically effective amount any of the compounds..
PCT/US2003/037592 2002-11-21 2003-11-20 Propargyl-trifluoromethoxy-amino-benzothiazole derivatives WO2004047756A2 (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
BR0315704-0A BR0315704A (en) 2002-11-21 2003-11-20 Propargyl trifluoromethoxy amino amino benzothiazole derivatives
CA002507414A CA2507414A1 (en) 2002-11-21 2003-11-20 Propargyl-trifluoromethoxy-amino-benzothiazole derivatives
EP03787112A EP1569641A2 (en) 2002-11-21 2003-11-20 Propargyl-trifluoromethoxy-amino-benzothiazole derivatives
JP2004555702A JP2006507350A (en) 2002-11-21 2003-11-20 Propargyl-trifluoromethoxy-amino-benzothiazole derivative
AU2003295898A AU2003295898A1 (en) 2002-11-21 2003-11-20 Propargyl-trifluoromethoxy-amino-benzothiazole derivatives
MXPA05005414A MXPA05005414A (en) 2002-11-21 2003-11-20 Propargyl-trifluoromethoxy-amino-benzothiazole derivatives.
NO20052979A NO20052979L (en) 2002-11-21 2005-06-17 Propargyl trifluoromethoxy-amino-benzothiazole.
IS7906A IS7906A (en) 2002-11-21 2005-06-22 Propergyl-trifluoromethoxy-amino-benzothiazole derivatives

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US30154002A 2002-11-21 2002-11-21
US10/301,540 2002-11-21

Publications (2)

Publication Number Publication Date
WO2004047756A2 WO2004047756A2 (en) 2004-06-10
WO2004047756A3 true WO2004047756A3 (en) 2004-07-08

Family

ID=32392394

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2003/037592 WO2004047756A2 (en) 2002-11-21 2003-11-20 Propargyl-trifluoromethoxy-amino-benzothiazole derivatives

Country Status (13)

Country Link
EP (1) EP1569641A2 (en)
JP (1) JP2006507350A (en)
KR (1) KR20050083951A (en)
CN (1) CN1741802A (en)
AU (1) AU2003295898A1 (en)
BR (1) BR0315704A (en)
CA (1) CA2507414A1 (en)
IS (1) IS7906A (en)
MX (1) MXPA05005414A (en)
NO (1) NO20052979L (en)
RU (1) RU2005119307A (en)
WO (1) WO2004047756A2 (en)
ZA (1) ZA200504988B (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2621490A4 (en) 2010-09-29 2014-04-02 Teva Pharma Propargyl-trifluoromethoxy-aminobenzothiazole derivatives, their preparation and use
CN103340859A (en) * 2013-06-04 2013-10-09 中国科学院昆明动物研究所 Method for establishing non-human primate animal model of parkinson disease by lateral ventricle administration of MPP<+>

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4535088A (en) * 1982-12-21 1985-08-13 Shionogi & Co., Ltd. Propynylaminothiazole derivatives

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4535088A (en) * 1982-12-21 1985-08-13 Shionogi & Co., Ltd. Propynylaminothiazole derivatives

Also Published As

Publication number Publication date
IS7906A (en) 2005-06-22
ZA200504988B (en) 2006-08-30
MXPA05005414A (en) 2006-05-25
NO20052979D0 (en) 2005-06-17
NO20052979L (en) 2005-08-19
CN1741802A (en) 2006-03-01
BR0315704A (en) 2005-09-06
EP1569641A2 (en) 2005-09-07
CA2507414A1 (en) 2004-06-10
RU2005119307A (en) 2006-01-27
WO2004047756A2 (en) 2004-06-10
AU2003295898A1 (en) 2004-06-18
KR20050083951A (en) 2005-08-26
JP2006507350A (en) 2006-03-02

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