WO2006114400A1 - Novel oxadiazole derivatives and their medical use - Google Patents

Novel oxadiazole derivatives and their medical use Download PDF

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Publication number
WO2006114400A1
WO2006114400A1 PCT/EP2006/061773 EP2006061773W WO2006114400A1 WO 2006114400 A1 WO2006114400 A1 WO 2006114400A1 EP 2006061773 W EP2006061773 W EP 2006061773W WO 2006114400 A1 WO2006114400 A1 WO 2006114400A1
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Prior art keywords
nitro
oxadiazol
phenyl
pyridine
cycloalkyl
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PCT/EP2006/061773
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English (en)
French (fr)
Inventor
Bjarne H. Dahl
Dan Peters
Gunnar M. Olsen
Daniel B. Timmermann
Susanne JØRGENSEN
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NTG Nordic Transport Group AS
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Neurosearch AS
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Priority to US11/919,146 priority Critical patent/US8017631B2/en
Priority to JP2008508201A priority patent/JP2008539195A/ja
Priority to MX2007013263A priority patent/MX2007013263A/es
Priority to AT06754801T priority patent/ATE477253T1/de
Priority to DE602006016104T priority patent/DE602006016104D1/de
Priority to CA002606087A priority patent/CA2606087A1/en
Priority to AU2006239418A priority patent/AU2006239418A1/en
Priority to EP06754801A priority patent/EP1881979B1/en
Application filed by Neurosearch AS filed Critical Neurosearch AS
Publication of WO2006114400A1 publication Critical patent/WO2006114400A1/en
Priority to IL186360A priority patent/IL186360A0/en
Anticipated expiration legal-status Critical
Priority to NO20076036A priority patent/NO20076036L/no
Priority to US13/194,193 priority patent/US20110294856A1/en
Ceased legal-status Critical Current

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Definitions

  • This invention relates to novel oxadiazole derivatives, which are found to be modulators of the nicotinic acetylcholine receptors. Due to their pharmacological profile the compounds of the invention may be useful for the treatment of diseases or disorders as diverse as those related to the cholinergic system of the central nervous system (CNS), the peripheral nervous system (PNS), diseases or disorders related to smooth muscle contraction, endocrine diseases or disorders, diseases or disorders related to neuro-degeneration, diseases or disorders related to inflammation, pain, and withdrawal symptoms caused by the termination of abuse of chemical substances.
  • CNS central nervous system
  • PNS peripheral nervous system
  • acetylcholine exert its biological effect via two types of cholinergic receptors, the muscarinic Acetyl Choline Receptors (mAChR) and the nicotinic Acetyl Choline Receptors (nAChR).
  • mAChR muscarinic Acetyl Choline Receptors
  • nAChR nicotinic Acetyl Choline Receptors
  • the present invention is devoted to the provision novel modulators of the nicotinic receptors, which modulators are useful for the treatment of diseases or disorders related to the nicotinic acetylcholine receptor (nAChR). Due to their pharmacological profile the compounds of the invention may be useful for the treatment of diseases or disorders as diverse as those related to the cholinergic system of the central nervous system (CNS), the peripheral nervous system (PNS), diseases or disorders related to smooth muscle contraction, endocrine diseases or disorders, diseases or disorders related to neuro-degeneration, diseases or disorders related to inflammation, pain, and withdrawal symptoms caused by the termination of abuse of chemical substances, in particular nicotine.
  • CNS central nervous system
  • PNS peripheral nervous system
  • diseases or disorders related to smooth muscle contraction endocrine diseases or disorders
  • diseases or disorders related to neuro-degeneration diseases or disorders related to inflammation, pain, and withdrawal symptoms caused by the termination of abuse of chemical substances, in particular nicotine.
  • n O, 1 , 2 or 3;
  • Ar 1 represents an monocyclic carbocyclic or heterocyclic group selected from cycloalkyl, phenyl, thienyl, furanyl, pyridinyl, and pyrazinyl, which monocyclic carbocyclic or heterocyclic group is optionally substituted one or more times with substituents selected from the group consisting of alkyl, cycloalkyl, cycloalkyl-alkyl, halo, haloalkyl, hydroxy, alkoxy, haloalkoxy, nitro and cyano; and
  • Ar 2 represents an aromatic monocyclic heterocyclic group selected from phenyl, thienyl, furanyl, pyrrolyl, pyrazolyl, thiazolyl, 1 ,3,4-thiadiazolyl and pyridinyl which aromatic monocyclic heterocyclic group is optionally substituted one or more times with substituents selected from the group consisting of alkyl, cycloalkyl, cycloalkyl-alkyl, halo, haloalkyl, hydroxy, alkoxy, haloalkoxy, nitro, cyano and amino.
  • the invention provides pharmaceutical compositions comprising a therapeutically effective amount of the oxadiazole derivative of the invention, or a pharmaceutically-acceptable addition salt thereof, together with at least one pharmaceutically-acceptable carrier or diluent.
  • the invention relates to the use of the oxadiazole derivative of the invention, or a pharmaceutically-acceptable addition salt thereof, for the manufacture of pharmaceutical compositions/medicaments for the treatment, prevention or alleviation of a disease or a disorder or a condition of a mammal, including a human, which disease, disorder or condition is responsive to modulation of cholinergic receptors.
  • the invention provides a method for treatment, prevention or alleviation of diseases, disorders or conditions of a living animal body, including a human, which disorder, disease or condition is responsive to modulation of cholinergic receptors, and which method comprises the step of administering to such a living animal body in need thereof a therapeutically effective amount of the oxadiazole derivative of the invention.
  • the invention provides oxadiazole derivatives of Formula I
  • n O, 1 , 2 or 3;
  • Ar 1 represents an monocyclic carbocyclic or heterocyclic group selected from cycloalkyl, phenyl, thienyl, furanyl, pyridinyl, and pyrazinyl, which monocyclic carbocyclic or heterocyclic group is optionally substituted one or more times with substituents selected from the group consisting of alkyl, cycloalkyl, cycloalkyl-alkyl, halo, haloalkyl, hydroxy, alkoxy, haloalkoxy, nitro and cyano; and
  • Ar 2 represents an aromatic monocyclic heterocyclic group selected from phenyl, thienyl, furanyl, pyrrolyl, pyrazolyl, thiazolyl, 1 ,3,4-thiadiazolyl and pyridinyl which aromatic monocyclic heterocyclic group is optionally substituted one or more times with substituents selected from the group consisting of alkyl, cycloalkyl, cycloalkyl-alkyl, halo, haloalkyl, hydroxy, alkoxy, haloalkoxy, nitro, cyano and amino.
  • Ar 1 represents cycloalkyl, in particular cyclopropyl.
  • Ar 1 represents phenyl, optionally substituted with fluoro, chloro or nitro. In a further more preferred embodiment Ar 1 represents phenyl, optionally substituted with chloro.
  • Ar 1 represents an aromatic monocyclic heterocyclic group selected from thienyl, furanyl, pyridinyl, and pyrazinyl, which monocyclic carbocyclic or heterocyclic group is optionally substituted one or more times with substituents selected from the group consisting of alkyl, cycloalkyl, cycloalkyl-alkyl, halo, haloalkyl, hydroxy, alkoxy, haloalkoxy, nitro and cyano.
  • Ar 2 represents an aromatic monocyclic heterocyclic group selected from furanyl, pyrrolyl, and pyrazolyl, which aromatic monocyclic heterocyclic group is optionally substituted one or two times with substituents selected from the group consisting of alkyl, cycloalkyl, cycloalkyl-alkyl, halo, haloalkyl, hydroxy, alkoxy, haloalkoxy, nitro and cyano.
  • Ar 2 represents an aromatic monocyclic heterocyclic group selected from furanyl, pyrrolyl, and pyrazolyl, which aromatic monocyclic heterocyclic group is optionally substituted with alkyl, halo, haloalkyl, hydroxy, alkoxy, haloalkoxy, nitro or cyano.
  • Ar 2 represents an aromatic monocyclic heterocyclic group selected from furanyl, pyrrolyl, and pyrazolyl, which aromatic monocyclic heterocyclic group is optionally substituted with alkyl, in particular methyl; or nitro.
  • Ar 2 represents phenyl, optionally substituted with alkyl, in particular methyl, ethyl or propyl; halo, in particular fluoro or chloro; haloalkyl, in particular trifluoromethyl; nitro; cyano or amino.
  • Ar 2 represents thienyl or furanyl, optionally substituted with alkyl, in particular methyl, ethyl or propyl; halo, in particular fluoro or chloro; haloalkyl, in particular trifluoromethyl; nitro; cyano or amino.
  • the oxadiazole derivative of the invention is a compound of Formula I n is 0 or 1 ;
  • Ar 2 represents thienyl, furanyl, pyrrolyl, or pyrazolyl, which aromatic monocyclic heterocyclic group is optionally substituted with alkyl, in particular methyl: halo, in particular fluoro or chloro; haloalkyl, in particular trifluoromethyl; hydroxyl; alkoxy, in particular methoxy or ethoxy; haloalkoxy, in particular trifluoromethoxy; nitro or cyano.
  • the oxadiazole derivative of the invention is a compound of Formula I wherein n is O or 1 ; Ar 1 phenyl, optionally substituted one or two times with substituents selected from the group consisting of alkyl, cycloalkyl, cycloalkyl-alkyl, halo, haloalkyl, hydroxy, alkoxy, haloalkoxy, nitro or cyano; and
  • Ar 1 represents thienyl or furanyl
  • Ar 2 represents thienyl or furanyl, optionally substituted with alkyl, cycloalkyl, cycloalkyl-alkyl, halo, haloalkyl, hydroxy, alkoxy, haloalkoxy, nitro, cyano or amino.
  • Ar 2 represents phenyl, thienyl, furanyl, pyrrolyl, pyrazolyl or thiazolyl, optionally substituted with alkyl, cycloalkyl, cycloalkyl-alkyl, halo, haloalkyl, hydroxy, alkoxy, haloalkoxy, nitro, cyano and amino.
  • the oxadiazole derivative of the invention is a compound of Formula I wherein n is 0;
  • the oxadiazole derivative of the invention is a compound of Formula I wherein n is 1 ;
  • an alkyl group designates a univalent saturated, straight or branched hydrocarbon chain.
  • the hydrocarbon chain preferably contain of from one to eighteen carbon atoms (d-i ⁇ -alkyl), more preferred of from one to six carbon atoms (C- ⁇ - 6 -alkyl; lower alkyl), including pentyl, isopentyl, neopentyl, tertiary pentyl, hexyl and isohexyl.
  • alkyl represents a Ci -4 - alkyl group, including butyl, isobutyl, secondary butyl, and tertiary butyl.
  • alkyl represents a d- 3 -alkyl group, which may in particular be methyl, ethyl, propyl or isopropyl.
  • a cycloalkyl group designates a cyclic alkyl group, preferably containing of from three to seven carbon atoms (Ca-y-cycloalkyl), including cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl.
  • a cycloalkyl-alkyl group designates a cycloalkyl group as defined above, which cycloalkyl group is substituted on an alkyl group as also defined above.
  • Examples of preferred cycloalkyl-alkyl groups of the invention include cyclopropylmethyl and cyclopropylethyl.
  • an alkoxy group designates an "alkyl-O-" group, wherein alkyl is as defined above. Examples of preferred alkoxy groups of the invention include methoxy and ethoxy.
  • a cycloalkoxy group designates a "cycloalkyl-O-" group, wherein cycloalkyl is as defined above.
  • a cyano-alkyl group designates an alkyl group substituted with CN, wherein alkyl is as defined above.
  • halo represents fluoro, chloro, bromo or iodo
  • haloalkyl group designates an alkyl group as defined herein, which alkyl group is substituted one or more times with halo.
  • a trihalomethyl group represents e.g. a trifluoromethyl group, a trichloromethyl group, and similar trihalo- substituted methyl groups.
  • Preferred haloalkyl groups of the invention include trihalogenmethyl, preferably -CF 3 .
  • a haloalkoxy group designates an alkoxy group as defined herein, which alkoxy group is substituted one or more times with halo.
  • Preferred haloalkoxy groups of the invention include trihalogenmethoxy, preferably -OCF 3 .
  • heteroaryl group designates an aromatic mono- or polycyclic heterocyclic group, which holds one or more heteroatoms in its ring structure.
  • Preferred heteroatoms include nitrogen (N), oxygen (O) and sulphur (S).
  • the oxadiazole derivative of the invention may be provided in any form suitable for the intended administration. Suitable forms include pharmaceutically (i.e. physiologically) acceptable salts, and pre- or prodrug forms of the compound of the invention.
  • Examples of pharmaceutically acceptable addition salts include, without limitation, the non-toxic inorganic and organic acid addition salts such as the hydrochloride, the hydrobromide, the nitrate, the perchlorate, the phosphate, the sulphate, the formate, the acetate, the aconate, the ascorbate, the benzenesulphonate, the benzoate, the cinnamate, the citrate, the embonate, the enantate, the fumarate, the glutamate, the glycolate, the lactate, the maleate, the malonate, the mandelate, the methanesulphonate, the naphthalene-2-sulphonate derived, the phthalate, the salicylate, the sorbate, the stearate, the succinate, the tartrate, the toluene-p- sulphonate, and the like.
  • Such salts may be formed by procedures well known and described in the art.
  • the disease, disorder or condition relates to the central nervous system.
  • the disease, disorder or condition is a cognitive disorder, learning deficit, memory deficits and dysfunction, Alzheimer's disease, attention deficit, attention deficit hyperactivity disorder (ADHD), Tourette's syndrome, psychosis, depression, bipolar disorder, mania, manic depression, schizophrenia, cognitive or attention deficits related to schizophrenia, obsessive compulsive disorders (OCD), panic disorders, eating disorders such as anorexia nervosa, bulimia and obesity, narcolepsy, nociception, AIDS-dementia, senile dementia, autism, Parkinson's disease, Huntington's disease, amyotrophic lateral sclerosis (ALS), anxiety, non-OCD anxiety disorders, convulsive disorders, convulsions, epilepsy, neurodegenerative disorders, transient anoxia, induced neuro- degeneration, neuropathy, diabetic neuropathy, periferic dyslexia, tardive dyskinesia, hyperkinesia, pain, mild pain, moderate or severe pain, pain of acute, chronic or
  • the compounds of the invention are used for the treatment, prevention or alleviation of a neurodegenerative disorder, transient anoxia, or induced neuro-degeneration.
  • the compounds of the invention are used for the treatment, prevention or alleviation of diabetic neuropathy, schizophrenia, cognitive or attentional deficits related to schizophrenia, or depression.
  • the compounds of the invention are used the treatment of withdrawal symptoms caused by termination of use of addictive substances, in particular nicotine containing products such as tobacco, opioids such as heroin, cocaine and morphine, benzodiazepines, benzodiazepine-like drugs, and alcohol.
  • addictive substances in particular nicotine containing products such as tobacco, opioids such as heroin, cocaine and morphine, benzodiazepines, benzodiazepine-like drugs, and alcohol.
  • the compounds of the invention are used for the treatment of anxiety, cognitive disorders, learning deficit, memory deficits and dysfunction, Alzheimer's disease, attention deficit, attention deficit hyperactivity disorder (ADHD), Parkinson's disease, Huntington's disease, Amyotrophic Lateral Sclerosis, Gilles de Ia Tourette's syndrome, psychosis, depression, mania, manic depression, schizophrenia, obsessive compulsive disorders (OCD), panic disorders, eating disorders such as anorexia nervosa, bulimia and obesity, narcolepsy, nociception, AIDS-dementia, senile dementia, periferic neuropathy, autism, dyslexia, tardive dyskinesia, hyperkinesia, epilepsy, bulimia, post-traumatic syndrome, social phobia, sleeping disorders, pseudodementia, Ganser's syndrome, pre-menstrual syndrome, late luteal phase syndrome, chronic fatigue syndrome, mutism, trichotillomania, and jet-lag.
  • ADHD attention deficit
  • the compounds of the invention are used for the treatment of endocrine disorders, such as thyrotoxicosis, pheochromocytoma, hypertension and arrhythmias.
  • treatment covers treatment, prevention, prophylactics and alleviation of withdrawal symptoms and abstinence as well as treatment resulting in a voluntary diminished intake of the addictive substance.
  • the invention provides pharmaceutical compositions comprising the oxadiazole derivative of the invention, or a pharmaceutically acceptable salt or derivative thereof, together with one or more pharmaceutically acceptable carriers therefore, and, optionally, other therapeutic and/or prophylactic ingredients, know and used in the art.
  • the carrier(s) must be "acceptable” in the sense of being compatible with the other ingredients of the formulation and not harmful to the recipient thereof.
  • compositions containing of from about 0.1 to about 500 mg of active ingredient per individual dose, preferably of from about 1 to about 100 mg, most preferred of from about 1 to about 10 mg, are suitable for therapeutic treatments.
  • the activity is determined as a standard assay using a fluorometric method in a Fluorescent Image Plate Reader (FLIPR) as described below in more detail.
  • FLIPR Fluorescent Image Plate Reader
  • EC 50 values represent the concentration of the test substance, at which the nicotine-induced EC2 0 - 30 response is positively modulated such that the size of the response equals 50% of a maximal nicotine control response.
  • the maximal positively modulated response is determined relative to the reference (nicotine) response.

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AT06754801T ATE477253T1 (de) 2005-04-26 2006-04-24 Neuartige oxadiazol-derivate und deren medizinische verwendung
DE602006016104T DE602006016104D1 (de) 2005-04-26 2006-04-24 Neuartige oxadiazol-derivate und deren medizinische verwendung
CA002606087A CA2606087A1 (en) 2005-04-26 2006-04-24 Novel oxadiazole derivatives and their medical use
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EP06754801A EP1881979B1 (en) 2005-04-26 2006-04-24 Novel oxadiazole derivatives and their medical use
IL186360A IL186360A0 (en) 2005-04-26 2007-10-07 Novel oxadiazole derivatives and their medical use
NO20076036A NO20076036L (no) 2005-04-26 2007-11-23 Nye oksadiazolderivater og deres medisinske anvendelse
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