WO2000013682A3 - 4-quinolinemethanol derivatives as purine receptor antagonists.(ii) - Google Patents

4-quinolinemethanol derivatives as purine receptor antagonists.(ii) Download PDF

Info

Publication number
WO2000013682A3
WO2000013682A3 PCT/GB1999/002924 GB9902924W WO0013682A3 WO 2000013682 A3 WO2000013682 A3 WO 2000013682A3 GB 9902924 W GB9902924 W GB 9902924W WO 0013682 A3 WO0013682 A3 WO 0013682A3
Authority
WO
WIPO (PCT)
Prior art keywords
disease
ring
alkyl
hydrogen
aryl
Prior art date
Application number
PCT/GB1999/002924
Other languages
French (fr)
Other versions
WO2000013682A2 (en
Inventor
Roger John Gillespie
Joanne Lerpiniere
Paul Richard Giles
David Reginald Adams
Lars Jacob Stray Knutsen
Ian Anthony Cliffe
Original Assignee
Cerebrus Pharm Ltd
Roger John Gillespie
Joanne Lerpiniere
Paul Richard Giles
David Reginald Adams
Lars Jacob Stray Knutsen
Ian Anthony Cliffe
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 Cerebrus Pharm Ltd, Roger John Gillespie, Joanne Lerpiniere, Paul Richard Giles, David Reginald Adams, Lars Jacob Stray Knutsen, Ian Anthony Cliffe filed Critical Cerebrus Pharm Ltd
Priority to EP99943124A priority Critical patent/EP1107761A2/en
Priority to US09/786,472 priority patent/US6608085B1/en
Priority to AU56402/99A priority patent/AU5640299A/en
Publication of WO2000013682A2 publication Critical patent/WO2000013682A2/en
Publication of WO2000013682A3 publication Critical patent/WO2000013682A3/en

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
    • A61K31/47—Quinolines; Isoquinolines
    • 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
    • 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

Abstract

Wherein: R1 is hydrogen or alkyl; R2 is selected from hydrogen, alkyl, aryl and 4,5,6,7 or 8 membered satured and partially unsaturated heterocyclic rings containing one or more heteroatoms selected from O, S and N; R3 and R4 are independently selected from hydrogen, alkyl, aryl, COR13, CO2R13, CONR13R14, CONR13NR14R15, SO2R13, SO2NR13R14, SO2NR13NR14R15 or may form a ring. Or R1 and R4 together may form a heterocyclic ring or R2 and R3 together may form a heterocyclic ring. R5 and R6 are independently selected from hydrogen, alkyl, aryl and heterocyclic with the proviso that where R3 and R5 together form a ring, then R3, and R4 do not also form a ring; or a pharmaceutically acceptable salt or prodrug thereof, in the manufacture of a medicament for the treatment or prevention of a disorder in which the blocking of purine receptors, particularly adenosine receptors and more particularly A2A receptors, may be beneficial, such as a movement disorder, for example, Parkinson's Disease or progressive supernuclear palsy, Huntingtons disease, multiple system atrophy, corticobasal degeneration, Wilsons disease, Hallerrorder-Spatz disease, progressive pallidal atrophy, Dopa-responsive dystonia-Parkinsonism, spasticity, Alzheimer's disease or other disorders of the basal ganglia which result in dyskinesias.
PCT/GB1999/002924 1998-09-04 1999-09-03 4-quinolinemethanol derivatives as purine receptor antagonists.(ii) WO2000013682A2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP99943124A EP1107761A2 (en) 1998-09-04 1999-09-03 4-quinolinemethanol derivatives as purine receptor antagonists (ii)
US09/786,472 US6608085B1 (en) 1998-09-04 1999-09-03 4-quinolinemethanol derivatives as purine receptor antagonists (II)
AU56402/99A AU5640299A (en) 1998-09-04 1999-09-03 4-quinolinemethanol derivatives as purine receptor antagonists.(ii)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9819384.0 1998-09-04
GBGB9819384.0A GB9819384D0 (en) 1998-09-04 1998-09-04 Chemical compounds II

Publications (2)

Publication Number Publication Date
WO2000013682A2 WO2000013682A2 (en) 2000-03-16
WO2000013682A3 true WO2000013682A3 (en) 2000-06-02

Family

ID=10838395

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1999/002924 WO2000013682A2 (en) 1998-09-04 1999-09-03 4-quinolinemethanol derivatives as purine receptor antagonists.(ii)

Country Status (5)

Country Link
US (1) US6608085B1 (en)
EP (1) EP1107761A2 (en)
AU (1) AU5640299A (en)
GB (1) GB9819384D0 (en)
WO (1) WO2000013682A2 (en)

Families Citing this family (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7906875B2 (en) * 1999-01-19 2011-03-15 Touchsensor Technologies, Llc Touch switches and practical applications therefor
GB9915437D0 (en) 1999-07-01 1999-09-01 Cerebrus Ltd Chemical compounds III
IT1318960B1 (en) * 2000-10-03 2003-09-19 Univ Degli Studi Milano METHOD FOR DIAGNOSIS OF HUNTINGTON KOREA AND ITS TREATMENT METHOD BASED ON THE ACTIVITY OF THE ADENYLATE CYCLASE.
GB0100624D0 (en) * 2001-01-10 2001-02-21 Vernalis Res Ltd Chemical compounds VII
GB0100623D0 (en) * 2001-01-10 2001-02-21 Vernalis Res Ltd Chemical compounds IV
GB0100620D0 (en) * 2001-01-10 2001-02-21 Vernalis Res Ltd Chemical cokpounds V
JP4376630B2 (en) 2002-01-28 2009-12-02 協和発酵キリン株式会社 Movement disorder treatment
ES2354875T3 (en) * 2002-12-19 2011-03-18 Schering Corporation USE OF ADENOSINE A2A RECEIVER ANTAGONISTS FOR THE TREATMENT OR PREVENTION OF EXTRAPIRAMIDAL SYNDROME.
US7834014B2 (en) * 2003-04-09 2010-11-16 Biogen Idec Ma Inc. A2a adenosine receptor antagonists
US7674791B2 (en) * 2003-04-09 2010-03-09 Biogen Idec Ma Inc. Triazolopyrazines and methods of making and using the same
US20070010522A1 (en) * 2003-04-09 2007-01-11 Chi Vu Triazolo[1,5-c]pyrimidines and pyrazolo[1,5-c]pyrimidines useful as a2a adenosine receptor antagonists
US20080070932A1 (en) * 2003-04-09 2008-03-20 Chi Vu Triazolo[ 1,5-A] Pyrimidines And Pyrazolo[ 1,5-A] Pyrimidines And Methods Of Making And Using The Same
US7285550B2 (en) * 2003-04-09 2007-10-23 Biogen Idec Ma Inc. Triazolotriazines and pyrazolotriazines and methods of making and using the same
BRPI0412263B1 (en) 2003-07-22 2019-10-15 Arena Pharmaceuticals, Inc. Diaryl and aryl heteroaryl urea derivatives, use and pharmaceutical composition containing them, as well as process for preparing said composition
WO2005041892A2 (en) * 2003-11-03 2005-05-12 Cornell Research Foundation, Inc Purine receptor inhibition as a therapeutic strategy in spinal cord and brain
TW200529845A (en) 2003-12-12 2005-09-16 Wyeth Corp Quinolines useful in treating cardiovascular disease
ES2273599B1 (en) 2005-10-14 2008-06-01 Universidad De Barcelona COMPOUNDS FOR THE TREATMENT OF HEADPHONE FIBRILATION.
US20110092488A1 (en) * 2005-10-28 2011-04-21 Geoffrey Dow Quninoline Methanol Compounds for the Treatment and Prevention of Parasitic Infections
KR20120011093A (en) * 2007-05-09 2012-02-06 화이자 인코포레이티드 Substituted heterocyclic derivatives and compositions and their pharmaceutical use as antibacterials
EP2254564A1 (en) 2007-12-12 2010-12-01 Glaxo Group Limited Combinations comprising 3-phenylsulfonyl-8-piperazinyl-1yl-quinoline
WO2009123714A2 (en) 2008-04-02 2009-10-08 Arena Pharmaceuticals, Inc. Processes for the preparation of pyrazole derivatives useful as modulators of the 5-ht2a serotonin receptor
GB0906579D0 (en) 2009-04-16 2009-05-20 Vernalis R&D Ltd Pharmaceuticals, compositions and methods of making and using the same
US9126946B2 (en) 2008-10-28 2015-09-08 Arena Pharmaceuticals, Inc. Processes useful for the preparation of 1-[3-(4-bromo-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenyl]-3-(2,4-difluoro-phenyl)urea and crystalline forms related thereto
CN102438624B (en) 2009-03-13 2016-03-30 阿德维纳斯治疗私人有限公司 The condensed pyramidine compounds replaced
WO2010144434A1 (en) * 2009-06-09 2010-12-16 The United States Of America, As Represented By The Secretary Of The Army, On Behalf Of U.S. Derivatives of mefloquine and associated methods for making and using
WO2011101861A1 (en) 2010-01-29 2011-08-25 Msn Laboratories Limited Process for preparation of dpp-iv inhibitors
EP2487157A1 (en) 2011-02-11 2012-08-15 Université de Picardie Jules Verne Enantioselective synthesis method of 4-aminoalcoholquinoline derivatives and the use
GB201406172D0 (en) * 2014-04-04 2014-05-21 Univ Nottingham Therapy and pharmaceutical composition
RU2017145976A (en) 2015-06-12 2019-07-15 Аксовант Сайенсиз Гмбх Diaryl- and arylheteroarylurea derivatives applicable for the prevention and treatment of behavioral disturbances during the REM phase of sleep
KR20180064373A (en) 2015-07-15 2018-06-14 엑소반트 사이언시즈 게엠베하 Diaryl and aryl heteroaryl urea derivatives as modulators of 5-HT2A serotonin receptors useful for the prevention and treatment of hallucinations associated with neurodegenerative diseases
CN111499558B (en) * 2020-05-14 2022-10-18 南开大学 Asymmetric reduction method of chiral spiro-bis-boron catalytic substituted pyridine and application thereof

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991001314A1 (en) * 1989-07-25 1991-02-07 Alkaloida Vegyészeti Gyár Process for the preparation of methyl-quinoline derivatives
EP0467710A2 (en) * 1990-07-19 1992-01-22 E.R. Squibb & Sons, Inc. Method for treating Parkinson's disease employing the ATP-sensitive potassium channel blocker quinine
EP0467709A2 (en) * 1990-07-20 1992-01-22 E.R. Squibb & Sons, Inc. Use of an ATP-sensitive potassium channel blocker to treat neuronal insult
WO1998048784A2 (en) * 1997-04-28 1998-11-05 The University Of British Columbia Method and composition for modulating amyloidosis
WO1999026627A1 (en) * 1997-11-26 1999-06-03 Cerebrus Limited (-)-mefloquine to block purinergic receptors and to treat movement or neurodegenerative disorders

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1990012797A1 (en) * 1989-04-19 1990-11-01 The United States Of America, As Represented By The Secretary, U.S. Department Of Commerce Sulfer-containing xanthine derivatives as adenosin antagonists
US5786360A (en) * 1996-11-19 1998-07-28 Link Technology Incorporated A1 adenosine receptor antagonists
SE9702001D0 (en) 1997-05-28 1997-05-28 Astra Pharma Prod Novel compounds
US6117884A (en) 1997-07-31 2000-09-12 Daeuble; John 4-substituted quinoline derivatives having fungicidal activity

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991001314A1 (en) * 1989-07-25 1991-02-07 Alkaloida Vegyészeti Gyár Process for the preparation of methyl-quinoline derivatives
EP0467710A2 (en) * 1990-07-19 1992-01-22 E.R. Squibb & Sons, Inc. Method for treating Parkinson's disease employing the ATP-sensitive potassium channel blocker quinine
EP0467709A2 (en) * 1990-07-20 1992-01-22 E.R. Squibb & Sons, Inc. Use of an ATP-sensitive potassium channel blocker to treat neuronal insult
WO1998048784A2 (en) * 1997-04-28 1998-11-05 The University Of British Columbia Method and composition for modulating amyloidosis
WO1999026627A1 (en) * 1997-11-26 1999-06-03 Cerebrus Limited (-)-mefloquine to block purinergic receptors and to treat movement or neurodegenerative disorders

Non-Patent Citations (9)

* Cited by examiner, † Cited by third party
Title
ADAM, SOLANGE: "Nor-mefloquine: Sterospecific synthesis and biological properties", BIOORG. MED. CHEM. LETT. (1992), 2(1), 53-8, XP000889818 *
BLUMBERGS ET AL: "Antimalarials. 7. 2,8-bis(trifluoromethyl)-4-quinolinemethanols", JOURNAL OF MEDICINAL CHEMISTRY,US,AMERICAN CHEMICAL SOCIETY. WASHINGTON, vol. 18, no. 11, 1975, pages 1122 - 1126-1126, XP002110895, ISSN: 0022-2623 *
CARROL ET AL: "Optical isomers of aryl-2-piperidylmethanol antimalarial agents. Preparation, optical purity, and absolute stereochemistry", JOURNAL OF MEDICINAL CHEMISTRY,US,AMERICAN CHEMICAL SOCIETY. WASHINGTON, vol. 17, no. 2, 1 January 1974 (1974-01-01), pages 210 - 219, XP002093258, ISSN: 0022-2623 *
GO, M. L. ET AL: "Effects of mefloquine on Ca2+ uptake by crude microsomes of rabbit skeletal muscle", ARCH. INT. PHARMACODYN. THER. (1995), 329(2), 255-71, XP000889822 *
GO, MEI LIN ET AL: "Pharmacological activity and structure-activity relationship of (.+-.)-erythro-mefloquine and related compounds on the isolated mouse phrenic nerve diaphragm preparation", BIOL. PHARM. BULL. (1993), 16(7), 668-74, XP000889819 *
NGIAM ET AL: "Stereospecific inhibition of cholinesterases by mefloquine", CHEMICAL AND PHARMACEUTICAL BULLETIN,JP,PHARMACEUTICAL SOCIETY OF JAPAN. TOKYO, vol. 35, no. 1, 1 January 1987 (1987-01-01), pages 409 - 412, XP002093900, ISSN: 0009-2363 *
PINDER, ROGER M. ET AL: "Antimalarials. II..alpha.-(2-Piperidyl)- and.alpha.-(2-pyridyl)- 2-trifluoromethyl-4-quinolinemethanols", J. MED. CHEM. (1968), 11(2), 267-9, XP000877337 *
RAINSFORD, K. D.: "Effects of antimalarial drugs on interleukin 1-induced cartilage proteoglycan degradation in vitro", J. PHARM. PHARMACOL. (1986), 38(11), 829-33, XP000889827 *
ROESNER, MANFRED ET AL: "Structure, chemistry, and antimalarial properties of mefloquine-aziridine", HETEROCYCLES (1981), 15(2), 925-33, XP000889902 *

Also Published As

Publication number Publication date
GB9819384D0 (en) 1998-10-28
EP1107761A2 (en) 2001-06-20
AU5640299A (en) 2000-03-27
WO2000013682A2 (en) 2000-03-16
US6608085B1 (en) 2003-08-19

Similar Documents

Publication Publication Date Title
WO2000013682A3 (en) 4-quinolinemethanol derivatives as purine receptor antagonists.(ii)
WO2000013681A3 (en) 4-quinolinemethanol derivatives as purine receptor antagonists (i)
Bertino Toward improved selectivity in cancer chemotherapy: the Richard and Hinda Rosenthal Foundation Award Lecture
CA2473864A1 (en) Composition for use in treating patients suffering from movement disorder
HK1083838A1 (en) A2a adenosine receptor antagonists
ATE297208T1 (en) EXTENDED-RELEASE TABLET FOR THE TREATMENT OF PARKINSON'S DISEASE
BG103417A (en) Condensed pyrimidine bicyclic derivatives
UA66825C2 (en) Azapolycyclic compounds condensed with aryl
GEP20043303B (en) Polycycloalkylpurines as Adenosine Receptor Antagonists
AU6770290A (en) Substituted cyclohexanols as central nervous system agents
HUP0103542A2 (en) 4,4-biarylpiperidine derivatives with opioid receptor activity and pharmaceutical compositions containing them
UA72881C2 (en) Thienopyrimidine and derivatives of thienopyrimidine as anticancer agents
HUT52769A (en) Process for producing pyrimidine derivatives and pharmaceutical compositions containing them
MXPA04000886A (en) DERIVATIVES OF TRIAZOLYL-IMIDAZOPYRIDINE AND OF THE TRIAZOLYLPURINES USEFUL AS LIGANDS OF THE ADENOSINE A2a.
AU5818994A (en) Application of carbamazepine and oxcarbazepine in the treatment of parkinson's disease and parkinsonian syndromes
TWI265928B (en) A61k 31/4025 200601 a i htw a61p 25/00 200601 a n htw
DK1212060T3 (en) Use of nicotine or its derivatives and L-DOPA in a drug for the treatment of neurological disorders, especially Parkinson's disease
CZ226195A3 (en) The use of lamotrigin for preparing medicaments intended for treating neuronal degeneration caused by aids
GEP20032868B (en) Triazolo-Pyridazine Derivatives as Ligands for Gaba Receptors, Methods for Their Production, Pharmaceutical Compositions Containing the Same for Treatment and/or Prevention of disorders of Central Nervous System
GR3019782T3 (en) Substituted tetrahydropyridines and hydroxypiperidines as central nervous system agents
Delaney et al. Levels of endogenous adenosine in rat striatum. II. Regulation of basal and N-methyl-D-aspartate-induced levels by inhibitors of adenosine transport and metabolism
BR9814080A (en) Use of compounds for anti-pruritic activity
BG103687A (en) Atropisomers of 3-heteroaryl-4(3h)-quinazolinones for the treatment of neurodegenerative processes and conditions related to the central nervous system
Lee et al. Therapeutic effects of 9-β-d-arabinofuranosyladenine and 2′-deoxycoformycin combinations on intracerebral leukemia
ES8801281A1 (en) Benzo-(pyrano and thiopyrano)pyridines.

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A2

Designated state(s): AE AL AM AT AU AZ BA BB BG BR BY CA CH CN CR CU CZ DE DK DM EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MD MG MK MN MW MX NO NZ PL PT RO RU SD SE SG SI SK SL TJ TM TR TT UA UG US UZ VN YU ZA ZW

AL Designated countries for regional patents

Kind code of ref document: A2

Designated state(s): GH GM KE LS MW SD SL SZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
AK Designated states

Kind code of ref document: A3

Designated state(s): AE AL AM AT AU AZ BA BB BG BR BY CA CH CN CR CU CZ DE DK DM EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MD MG MK MN MW MX NO NZ PL PT RO RU SD SE SG SI SK SL TJ TM TR TT UA UG US UZ VN YU ZA ZW

AL Designated countries for regional patents

Kind code of ref document: A3

Designated state(s): GH GM KE LS MW SD SL SZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN GW ML MR NE SN TD TG

WWE Wipo information: entry into national phase

Ref document number: 1999943124

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 09786472

Country of ref document: US

WWP Wipo information: published in national office

Ref document number: 1999943124

Country of ref document: EP

REG Reference to national code

Ref country code: DE

Ref legal event code: 8642

WWW Wipo information: withdrawn in national office

Ref document number: 1999943124

Country of ref document: EP