WO2001085727A1 - Azabicyclic carbamates and their use as alpha-7 nicotinic acetylcholine receptor agonists - Google Patents

Azabicyclic carbamates and their use as alpha-7 nicotinic acetylcholine receptor agonists Download PDF

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Publication number
WO2001085727A1
WO2001085727A1 PCT/EP2001/005008 EP0105008W WO0185727A1 WO 2001085727 A1 WO2001085727 A1 WO 2001085727A1 EP 0105008 W EP0105008 W EP 0105008W WO 0185727 A1 WO0185727 A1 WO 0185727A1
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WO
WIPO (PCT)
Prior art keywords
compound
formula
acid addition
free base
addition salt
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/EP2001/005008
Other languages
English (en)
French (fr)
Inventor
Joachim Nozulak
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.)
Novartis Pharma GmbH Austria
Novartis AG
Original Assignee
Novartis Erfindungen Verwaltungs GmbH
Novartis AG
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
Priority to DE60102581T priority Critical patent/DE60102581T2/de
Priority to HU0301866A priority patent/HUP0301866A2/hu
Priority to PL01357435A priority patent/PL357435A1/xx
Priority to MXPA02010892A priority patent/MXPA02010892A/es
Priority to HK03104830.3A priority patent/HK1054223B/en
Priority to BR0110521-3A priority patent/BR0110521A/pt
Priority to JP2001582328A priority patent/JP4898062B2/ja
Priority to IL15241701A priority patent/IL152417A0/xx
Priority to US10/258,920 priority patent/US6780861B2/en
Priority to NZ522226A priority patent/NZ522226A/en
Priority to EP01936319A priority patent/EP1282620B1/en
Priority to SI200130116T priority patent/SI1282620T1/xx
Priority to DK01936319T priority patent/DK1282620T3/da
Priority to AT01936319T priority patent/ATE263167T1/de
Priority to AU6225701A priority patent/AU6225701A/xx
Priority to KR1020027014760A priority patent/KR20020093974A/ko
Application filed by Novartis Erfindungen Verwaltungs GmbH, Novartis AG filed Critical Novartis Erfindungen Verwaltungs GmbH
Priority to CA002407972A priority patent/CA2407972C/en
Priority to AU2001262257A priority patent/AU2001262257B2/en
Priority to SK1561-2002A priority patent/SK15612002A3/sk
Publication of WO2001085727A1 publication Critical patent/WO2001085727A1/en
Priority to NO20025280A priority patent/NO20025280D0/no
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
    • C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
    • 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
    • A61K31/439—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 the ring forming part of a bridged ring system, e.g. quinuclidine
    • 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
    • A61P25/22—Anxiolytics
    • 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
    • A61P25/26—Psychostimulants, e.g. nicotine, cocaine
    • 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

Definitions

  • the present invention relates to novel azabicyclic carbamates, their preparation, their use as pharmaceuticals and pharmaceutical compositions containing them.
  • Ri, R 2 and R 3 independently, are hydrogen or (C 1-4 )alkyl and A is a group of formula
  • X is O, S, NH or CH 2 and R 4 and R 5 , independently, are hydrogen, halogen, hydroxy, (C 1 . 4 )alkyl, (C 1-4 )alkoxy, (C ! . 4 )alkylthio, (C ⁇ . 4 )alkylamino, nitro, trifluoromethyl or phenyl, in free base or acid addition salt form.
  • Halogen denotes fluorine, bromine, chlorine or iodine.
  • alkyl, alkoxy and alkylthio groups are branched or straight chain groups. They are preferably methyl, methoxy or methylthio groups.
  • the compounds may exist in optically active form or in form of mixtures of optical isomers, e.g. in form of racemic mixtures. All optical isomers and their mixtures including the racemic mixtures are part of the present invention.
  • the invention provides a process for the production of the compounds of formula I and their salts, comprising the step of reacting a compound of formula II
  • n, Ri and R 2 are as defined above, with a compound of formula HI
  • R and A are as defined above, and N, N'-carbonyldiimidazole or di(N- succinimidyl)carbonate, and recovering the resulting compound of formula I in free base or acid addition salt form.
  • the compound of formula III is reacted with N, N'-carbonyldiimidazole, and the resulting compound is reacted with the compound of formula II.
  • the reactions can be effected according to conventional methods, e.g. as described in the examples.
  • the starting materials of formula II, m and IV are known or may be obtained from known compounds, using conventional procedures.
  • agents of the invention exhibit valuable pharmacological properties when tested in vitro and in animals, and are therefore useful as pharmaceuticals.
  • the agents of the invention are ⁇ 7 nicotinic acetylcholine receptor (nAChR) agonists.
  • the agents of the invention display high affinity at the ⁇ 7 nAChR as shown in the following tests:
  • a functional assay for affinity at human ⁇ 7 nAChR is carried out with a rat pituitary cell line stably expressing the human ⁇ 7 nAChR. As a read out, the calcium influx upon stimulation of the receptor is used. In this assay, agents of the invention exhibit pECso values of about 5 to about 8.
  • agents of the invention show selectivity for the ⁇ 7 nAChR subtypes.
  • the agents of the invention induce significant sensory gating at concentrations of about 10 to about 40 ⁇ M.
  • the agents of the invention are therefore useful for the treatment of psychotic disorders such as schizophrenia, mania, depression and anxiety, and for the treatment of neurodegenerative disorders such as senile dementia, Alzheimer's disease and other intellectual impairment disorders, such as attention deficit hyperactivity disorders (ADHD); Parkinson's disease, Huntington's chorea, amyotrophic lateral sclerosis and multiple sclerosis.
  • ADHD attention deficit hyperactivity disorders
  • Parkinson's disease Huntington's chorea
  • amyotrophic lateral sclerosis and multiple sclerosis.
  • the appropriate dosage will of course vary depending upon, for example, the compound employed, the host, the mode of administration and the nature and severity of the condition being treated. However, in general, satisfactory results in animals are indicated to be obtained at a daily dosage of from about 0.01 to about 100, preferably from about 0.1 to about 50 mg/kg animal body weight. In larger mammals, for example humans, an indicated daily dosage is in the range from about 1 to about 500, preferably from about 5 to about 300 mg of an agent of the invention conveniently administered, for example, in divided doses up to four times a day or in sustained release form.
  • the agent of the invention may be administered by any conventional route, in particular enterally, preferably orally, for example in the form of tablets or capsules, or parenterally, for example in the form of injectable solutions or suspensions.
  • the present invention also provides an agent of the invention, for use as a pharmaceutical, e.g. for the treatment of any condition mentioned above.
  • the present invention furthermore provides a pharmaceutical composition
  • a pharmaceutical composition comprising an agent of the invention in association with at least one pharmaceutical carrier or diluent.
  • Such compositions may be manufactured in conventional manner.
  • Unit dosage forms contain, for example, from about 0.25 to about 150, preferably from about 1 to about 25 mg of a compound according to the invention.
  • the present invention provides the use of an agent of the invention, for the manufacture of a medicament for the treatment of any condition mentioned above.
  • the present invention provides a method for the treatment of any condition mentioned above, in a subject in need of such treatment, which comprises administering to such subject a therapeutically effective amount of an agent of the invention.
  • 3-Aminoquinuclidine dihydrochloride 996 mg (5.0 mmol) is added slowly to a stirred suspension of 676 mg (15.5 mmol) sodium hydride (dispersion 55%) in dimethylformamide (15 ml). Thereafter the suspension is stirred for another 90 minutes at room temperature and then carbobenzoxy chloride 0.72 ml (5.1 mmol) is added slowly. After another two hours at room temperature, the suspension is quenched by carefully adding water. The solvent is then evaporated at 70 °C / 16 mbar. The residue is taken up in water and ethyl acetate. The organic phase is separated and the water phase two-times re-extracted with ethyl acetate.
  • Triethylamine 1.05 ml (7.5 mmol) and 0.80 g di-(N-succinimidyl)carbonate are added to a solution of (4-butyl-phenyl)methanol 0.47 ml (2.75 mmol) in 15 ml dichloromethane. The initial suspension is stirred at room temperature for 45 minutes to become a clear solution. This mixture is added dropwise to a solution of 3- aminoquinuclidine 0.32 g (2.5 mmol) and 0.52 ml (1.5 mmol) triethylamine in 10 ml dichloromethane. The reaction mixture is subsequently stirred for another two hours at room temperature. Afterwards the mixture is washed with 20 ml water.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Neurology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biomedical Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Neurosurgery (AREA)
  • Psychiatry (AREA)
  • Psychology (AREA)
  • Hospice & Palliative Care (AREA)
  • Pain & Pain Management (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
PCT/EP2001/005008 2000-05-05 2001-05-03 Azabicyclic carbamates and their use as alpha-7 nicotinic acetylcholine receptor agonists Ceased WO2001085727A1 (en)

Priority Applications (20)

Application Number Priority Date Filing Date Title
EP01936319A EP1282620B1 (en) 2000-05-05 2001-05-03 Azabicyclic carbamates and their use as alpha-7 nicotinic acetylcholine receptor agonists
PL01357435A PL357435A1 (en) 2000-05-05 2001-05-03 Azabicyclic carbamates and their use as alpha-7 nicotinic acetylcholine receptor agonists
MXPA02010892A MXPA02010892A (es) 2000-05-05 2001-05-03 Carbamatos azabiciclicos y su uso como agonistas del receptor de acetilcolina alfa-7-nicotinico.
HK03104830.3A HK1054223B (en) 2000-05-05 2001-05-03 Azabicyclic carbamate and its use as alpha-7 nicotinic acetylcholine receptor antagonist
BR0110521-3A BR0110521A (pt) 2000-05-05 2001-05-03 Carbamatos azabicìclicos e seu uso como agonistas de receptores de alfa-7 acetilcolina nicotìnico
HU0301866A HUP0301866A2 (hu) 2000-05-05 2001-05-03 Azabiciklusos karbamátok mint alfa-7 nikotin/acetilkolin receptor agonisták, eljárás elżállításukra és ezeket tartalmazó gyógyszerkészítmények
IL15241701A IL152417A0 (en) 2000-05-05 2001-05-03 Azabicyclic carbamates and their use as alpha-7 nicotinic acetylcholine receptor agonists
US10/258,920 US6780861B2 (en) 2000-05-05 2001-05-03 Azabicyclic carbamates and their use as α-7 nicotinic acetylcholine receptor agonists
NZ522226A NZ522226A (en) 2000-05-05 2001-05-03 Azabicyclic carbamates and their use as alpha-7 nicotinic acetylcholine receptor agonists
SI200130116T SI1282620T1 (en) 2000-05-05 2001-05-03 Azabicyclic carbamates and their use as alpha-7 nicotinic acetylcholine receptor agonists
JP2001582328A JP4898062B2 (ja) 2000-05-05 2001-05-03 アザ二環式カルバメートおよびアルファ−７ニコチン性アセチルコリンレセプターアゴニストとしてのその使用
DE60102581T DE60102581T2 (de) 2000-05-05 2001-05-03 Azabizyklische carbamate und ihre anwendung als antagonisten des alpha-7 nikotinischen acetylcholin rezeptors
AT01936319T ATE263167T1 (de) 2000-05-05 2001-05-03 Azabizyklische carbamate und ihre anwendung als antagonisten des alpha-7 nikotinischen acetylcholin rezeptors
AU6225701A AU6225701A (en) 2000-05-05 2001-05-03 Azabicyclic carbamates and their use as alpha-7 nicotinic acetylcholine receptoragonists
KR1020027014760A KR20020093974A (ko) 2000-05-05 2001-05-03 아자비시클릭 카르밤산염 및 알파-７ 니코틴작용아세틸콜린 수용체 아고니스트로서의 이의 용도
DK01936319T DK1282620T3 (da) 2000-05-05 2001-05-03 Azabicycliske carbamater og deres anvendelse som antagonister af alpha-7-nikotiniske acetylcholinreceptorer
CA002407972A CA2407972C (en) 2000-05-05 2001-05-03 Azabicyclic carbamates and their use as alpha-7 nicotinic acetylcholine receptor agonists
AU2001262257A AU2001262257B2 (en) 2000-05-05 2001-05-03 Azabicyclic carbamates and their use as alpha-7 nicotinic acetylcholine receptor agonists
SK1561-2002A SK15612002A3 (sk) 2000-05-05 2001-05-03 Azabicyklické karbamáty, spôsob ich prípravy a farmaceutické prostriedky, ktoré ich obsahujú ako účinné látky
NO20025280A NO20025280D0 (no) 2000-05-05 2002-11-04 Azabicykliske karbamater og deres anvendelse som alfa-7 nikotinisk acetylkolinreseptoragonister

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB0010955.3 2000-05-05
GBGB0010955.3A GB0010955D0 (en) 2000-05-05 2000-05-05 Organic compounds

Publications (1)

Publication Number Publication Date
WO2001085727A1 true WO2001085727A1 (en) 2001-11-15

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2001/005008 Ceased WO2001085727A1 (en) 2000-05-05 2001-05-03 Azabicyclic carbamates and their use as alpha-7 nicotinic acetylcholine receptor agonists

Country Status (29)

Country Link
US (1) US6780861B2 (https=)
EP (1) EP1282620B1 (https=)
JP (1) JP4898062B2 (https=)
KR (1) KR20020093974A (https=)
CN (1) CN1167703C (https=)
AR (1) AR028073A1 (https=)
AT (1) ATE263167T1 (https=)
AU (2) AU2001262257B2 (https=)
BR (1) BR0110521A (https=)
CA (1) CA2407972C (https=)
CZ (1) CZ20023622A3 (https=)
DE (1) DE60102581T2 (https=)
DK (1) DK1282620T3 (https=)
ES (1) ES2218418T3 (https=)
GB (1) GB0010955D0 (https=)
HK (1) HK1054223B (https=)
HU (1) HUP0301866A2 (https=)
IL (1) IL152417A0 (https=)
MX (1) MXPA02010892A (https=)
NO (1) NO20025280D0 (https=)
NZ (1) NZ522226A (https=)
PE (1) PE20020221A1 (https=)
PL (1) PL357435A1 (https=)
PT (1) PT1282620E (https=)
RU (1) RU2002131886A (https=)
SK (1) SK15612002A3 (https=)
TR (1) TR200401007T4 (https=)
WO (1) WO2001085727A1 (https=)
ZA (1) ZA200208969B (https=)

Cited By (37)

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JPS6262265A (ja) * 1985-09-13 1987-03-18 Hitachi Ltd 復水器自動検査補修システム
WO2002085901A1 (en) * 2001-04-19 2002-10-31 Pharmacia & Upjohn Company Substituted azabicyclic moieties for the treatment of disease (nicotinic acethylcholine receptor agonists)
WO2003070728A3 (en) * 2002-02-15 2003-12-04 Upjohn Co Azabicyclo-substituted benzoylamides and thioamides for treatment of cns-related disorders
WO2004013136A1 (de) * 2002-07-29 2004-02-12 Bayer Healthcare Ag Benzothiophen-, benzofuran- und indolharnstoffe und deren verwendung als alpha7-achr agonisten
WO2003070731A3 (en) * 2002-02-19 2004-03-18 Upjohn Co Azabicyclic compounds for the treatment of disease
WO2004085433A3 (en) * 2003-03-28 2004-12-16 Upjohn Co Positive allosteric modulators of the nicotinic acetylcholine receptor
WO2007068475A1 (en) * 2005-12-16 2007-06-21 Novartis Ag (1-aza-bicyclo[3.3.1] n0n-4-yl)-[5-(ih-indol-5-yl)-heteroaryl]-amines as cholinergic ligands of the n-achr for the treatment of psychotic and neurodegenerative disorders
US7238715B2 (en) 2002-12-06 2007-07-03 The Feinstein Institute For Medical Research Treatment of pancreatitis using alpha 7 receptor-binding cholinergic agonists
US7273872B2 (en) 2002-12-06 2007-09-25 The Feinstein Institute For Medical Research Inhibition of inflammation using α 7 receptor-binding cholinergic agonists
US7425561B2 (en) 1998-12-11 2008-09-16 Targacept, Inc. 3-substituted-2(arylalkyl)-1-azabicycloalkanes and methods of use thereof
US7579362B2 (en) 2002-09-04 2009-08-25 Novartis Ag Aza-bicycloalkyl ethers and their use as alpha7-nAChR agonists
EP2135609A1 (en) 2004-11-05 2009-12-23 Novartis AG Combinations of nicotinic acetylcholine alpha 7 receptor agonists
US7674899B2 (en) 2004-02-04 2010-03-09 Neurosearch A/S Dimeric azacyclic compounds and their use
US7713976B2 (en) 2005-12-16 2010-05-11 Novartis Ag [(1H-indol-5-yl)-heteroaryloxy]-1-aza-bicylco[3.3.1]nonanes as cholinergic ligands of the n-AChR for the treatment of psychotic and neurodegenerative disorders
WO2011009890A2 (en) 2009-07-23 2011-01-27 Novartis Ag Use of azabicycloalkyl derivatives or pyrrolidine-2-one derivatives
WO2011036167A1 (en) 2009-09-22 2011-03-31 Novartis Ag Use of nicotinic acetylcholine receptor alpha 7 activators
US7981906B2 (en) 2007-08-02 2011-07-19 Targacept, Inc. (2S,3R)-N-(2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]oct-3-yl-benzofuran-2-carboxamide, novel salt forms, and methods of use thereof
US8173667B2 (en) 2005-10-21 2012-05-08 Novartis Ag 1-aza-bicycloalkyl derivatives
WO2012101060A1 (en) 2011-01-27 2012-08-02 Novartis Ag Use of nicotinic acetylcholine receptor alpha 7 activators
WO2012127393A1 (en) 2011-03-18 2012-09-27 Novartis Ag COMBINATIONS OF ALPHA 7 NICOTINIC ACETYLCHOLINE RECEPTOR ACTIVATORS AND mGluR5 ANTAGONISTS FOR USE IN DOPAMINE INDUCED DYSKINESIA IN PARKINSON'S DISEASE
WO2012146515A1 (en) * 2011-04-29 2012-11-01 Chiesi Farmaceutici S.P.A. Alkaloid ester and carbamate derivatives and medicinal compositions thereof
WO2013057687A2 (en) 2011-10-20 2013-04-25 Novartis Ag Biomarkers predictive of responsiveness to alpha 7 nicotinic acetylcholine receptor activator treatment
US8524866B2 (en) 2005-11-15 2013-09-03 The Feinstein Institute For Medical Research Antibodies to the alpha-7 nicotinic receptors and methods of treating inflammatory disorders with the same
US8609662B2 (en) 2004-07-14 2013-12-17 Novartis Ag 3-(heteroaryl-oxy)-2-alkyl-1-aza-bicycloalkyl derivatives as alpha. 7-nachr ligands for the treatment of CNS diseases
WO2014091388A2 (en) 2012-12-11 2014-06-19 Novartis Ag Biomarker predictive of responsiveness to alpha 7 nicotinic acetylcholine receptor activator treatment
WO2014111837A1 (en) 2013-01-15 2014-07-24 Novartis Ag Use of alpha 7 nicotinic acetylcholine receptor agonists
WO2014111838A1 (en) 2013-01-15 2014-07-24 Novartis Ag Use of alpha 7 nicotinic acetylcholine receptor agonists
WO2014111751A1 (en) 2013-01-15 2014-07-24 Novartis Ag Use of alpha 7 nicotinic receptor agonists for the treatment of narcolepsy
US8901151B2 (en) 2009-01-26 2014-12-02 Targacept, Inc. Preparation and therapeutic applications of (2S, 3R)-N-2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]OCT-3-yl)-3,5-difluorobenzamide
US8933090B2 (en) 2004-06-18 2015-01-13 Novartis Ag 1-aza-bicyclo[3.3.1]nonanes
US9724340B2 (en) 2015-07-31 2017-08-08 Attenua, Inc. Antitussive compositions and methods
AU2016244305B2 (en) * 2011-03-18 2018-05-24 Genzyme Corporation Glucosylceramide synthase inhibitors
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US11311525B2 (en) 2013-01-15 2022-04-26 Novartis Ag Use of alpha 7 nicotinic acetylcholine receptor agonists
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US12527776B2 (en) 2019-02-04 2026-01-20 Genzyme Corporation Treatment of ciliopathies using inhibitors of glucosylceramide synthase (GCS)

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