WO2003072055A3 - Propargylamino indan derivatives and propargylamino tetralin derivatives as brain-selective mao inhibitors - Google Patents

Propargylamino indan derivatives and propargylamino tetralin derivatives as brain-selective mao inhibitors Download PDF

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Publication number
WO2003072055A3
WO2003072055A3 PCT/US2003/005871 US0305871W WO03072055A3 WO 2003072055 A3 WO2003072055 A3 WO 2003072055A3 US 0305871 W US0305871 W US 0305871W WO 03072055 A3 WO03072055 A3 WO 03072055A3
Authority
WO
WIPO (PCT)
Prior art keywords
propargylamino
derivatives
brain
alkyl
tetralin
Prior art date
Application number
PCT/US2003/005871
Other languages
French (fr)
Other versions
WO2003072055A2 (en
Inventor
Eran Blaugrund
Yaacov Herzig
Jeffrey Sterling
Original Assignee
Teva Pharma
Teva Pharmaceuticals 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 Pharmaceuticals Inc filed Critical Teva Pharma
Priority to JP2003570802A priority Critical patent/JP2005523289A/en
Priority to AU2003219913A priority patent/AU2003219913A1/en
Priority to CA002477218A priority patent/CA2477218A1/en
Priority to EP03716197A priority patent/EP1490324A4/en
Publication of WO2003072055A2 publication Critical patent/WO2003072055A2/en
Publication of WO2003072055A3 publication Critical patent/WO2003072055A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C215/64—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with rings other than six-membered aromatic rings being part of the carbon skeleton
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
    • 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
    • A61P25/08—Antiepileptics; Anticonvulsants
    • 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
    • A61P25/24—Antidepressants
    • 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
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C219/26—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
    • C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane

Abstract

The subject invention provides derivatives of propargylamino indan (PAI) and propargylamino tetralin that selectively inhibit monoamine oxidase (MAO) in the brain, having the structure:, wherein R1 is OC (O) R9 and R2 is H, wherein R9 i s branched or unbranched C1 to C6 alkyl, aryl, or aralkyl, or R1 is OC (O) R4 and R2 is OC (O) R4, wherein R4 is branched or unbranched C1 to C6 alkyl, aryl, aralkyl or NR5R6, wherein R5 and R6 are each independently H, C1 to C8 alkyl, C6 to C12 aryl, C6 to C12 aralkyl or C6 to C12 cycloalkyl, each optionally substituted; wherein R3 is H or C1 to C6 alkyl; wherein n is 0 or 1; and wherein m is 1 or 2, or a pharmaceutically acceptable salt thereof. Additionally, the subject invention provides methods of treating neurological disorders using these compounds, uses of these compounds for the manufacture of medicaments for treating neurological disorders and processes for synthesis of these compounds.
PCT/US2003/005871 2002-02-27 2003-02-27 Propargylamino indan derivatives and propargylamino tetralin derivatives as brain-selective mao inhibitors WO2003072055A2 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
JP2003570802A JP2005523289A (en) 2002-02-27 2003-02-27 Propargylaminoindan derivatives and propargylaminotetralin derivatives as brain-selective MAO inhibitors
AU2003219913A AU2003219913A1 (en) 2002-02-27 2003-02-27 Propargylamino indan derivatives and propargylamino tetralin derivatives as brain-selective mao inhibitors
CA002477218A CA2477218A1 (en) 2002-02-27 2003-02-27 Propargylamino indan derivatives and propargylamino tetralin derivatives as brain-selective mao inhibitors
EP03716197A EP1490324A4 (en) 2002-02-27 2003-02-27 Propargylamino indan derivatives and propargylamino tetralin derivatives as brain-selective mao inhibitors

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US8567402A 2002-02-27 2002-02-27
US10/085,674 2002-02-27

Publications (2)

Publication Number Publication Date
WO2003072055A2 WO2003072055A2 (en) 2003-09-04
WO2003072055A3 true WO2003072055A3 (en) 2003-12-31

Family

ID=27765338

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2003/005871 WO2003072055A2 (en) 2002-02-27 2003-02-27 Propargylamino indan derivatives and propargylamino tetralin derivatives as brain-selective mao inhibitors

Country Status (5)

Country Link
EP (1) EP1490324A4 (en)
JP (1) JP2005523289A (en)
AU (1) AU2003219913A1 (en)
CA (1) CA2477218A1 (en)
WO (1) WO2003072055A2 (en)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2003290838A1 (en) 2002-11-15 2004-06-15 Teva Pharmaceutical Industries, Ltd. Use of rasagiline with or without riluzole to treat amyotrophic lateral sclerosis
MX2007010233A (en) 2005-02-23 2007-11-07 Teva Pharma Rasagiline formulations of improved content uniformity.
CA2600603A1 (en) 2005-02-24 2006-08-31 Teva Pharmaceutical Industries Ltd. Formulations of ladostigil tartrate
EP1890690A4 (en) 2005-06-02 2010-06-02 Jenrin Discovery Mao-b inhibitors useful for treating abesity
EP1906952A4 (en) 2005-07-01 2010-04-14 Jenrin Discovery Mao-b inhibitors useful for treating obesity
AU2006316585B2 (en) * 2005-11-17 2012-09-20 Teva Pharmaceutical Industries, Ltd. Methods for isolating propargylated aminoindans
US7572834B1 (en) 2005-12-06 2009-08-11 Teva Pharmaceutical Industries, Ltd. Rasagiline formulations and processes for their preparation
TW200744576A (en) 2006-02-24 2007-12-16 Teva Pharma Propargylated aminoindans, processes for preparation, and uses thereof
JP5769923B2 (en) 2006-04-03 2015-08-26 テバ ファーマシューティカル インダストリーズ リミティド Use of rasagiline for the treatment of restless legs syndrome

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3513244A (en) * 1966-07-16 1970-05-19 Aspro Nicholas Ltd Methods of lowering blood pressure in animals by administering secondary and tertiary amines
WO1994022495A1 (en) * 1993-03-31 1994-10-13 The Trustees Of The University Of Pennsylvania Dopamine d-3 and serotonin (5-ht1a) receptor ligands and imaging agents
US6303650B1 (en) * 1996-12-18 2001-10-16 Yissum Research Development Company Of The Hebrew University Of Jerusalem Aminoindan derivatives

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE9103745D0 (en) * 1991-12-18 1991-12-18 Wikstroem Haakan ARYL-TRIFLATES AND RELATED COMPOUNDS
AU1867095A (en) * 1994-01-10 1995-08-01 Technion Research & Development Foundation Ltd. 1-aminoindan derivatives and compositions thereof
WO1996036596A1 (en) * 1995-05-19 1996-11-21 Chiroscience Limited 3,4-disubstituted-phenylsulphonamides and their therapeutic use
CA2242598A1 (en) * 1996-02-21 1997-08-28 John Gary Montana Quinolones and their therapeutic use

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3513244A (en) * 1966-07-16 1970-05-19 Aspro Nicholas Ltd Methods of lowering blood pressure in animals by administering secondary and tertiary amines
WO1994022495A1 (en) * 1993-03-31 1994-10-13 The Trustees Of The University Of Pennsylvania Dopamine d-3 and serotonin (5-ht1a) receptor ligands and imaging agents
US6303650B1 (en) * 1996-12-18 2001-10-16 Yissum Research Development Company Of The Hebrew University Of Jerusalem Aminoindan derivatives

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP1490324A4 *

Also Published As

Publication number Publication date
AU2003219913A8 (en) 2003-09-09
AU2003219913A1 (en) 2003-09-09
WO2003072055A2 (en) 2003-09-04
EP1490324A4 (en) 2007-10-10
JP2005523289A (en) 2005-08-04
CA2477218A1 (en) 2003-09-04
EP1490324A2 (en) 2004-12-29

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