WO2007028654A1 - Pyridine derivatives and their use in the treatment of psychotic disorders - Google Patents

Pyridine derivatives and their use in the treatment of psychotic disorders Download PDF

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Publication number
WO2007028654A1
WO2007028654A1 PCT/EP2006/008845 EP2006008845W WO2007028654A1 WO 2007028654 A1 WO2007028654 A1 WO 2007028654A1 EP 2006008845 W EP2006008845 W EP 2006008845W WO 2007028654 A1 WO2007028654 A1 WO 2007028654A1
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Prior art keywords
alkyl
mmol
represent
solution
compound according
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PCT/EP2006/008845
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English (en)
French (fr)
Inventor
Giuseppe Alvaro
Daniele Andreotti
Sandro Belvedere
Romano Di Fabio
Alessandro Falchi
Riccardo Giovannini
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SmithKline Beecham Corp
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SmithKline Beecham Corp
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First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=37546936&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=WO2007028654(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority claimed from GB0518472A external-priority patent/GB0518472D0/en
Priority claimed from GB0611153A external-priority patent/GB0611153D0/en
Priority to BRPI0615787A priority Critical patent/BRPI0615787B8/pt
Priority to HR20110457T priority patent/HRP20110457T1/hr
Priority to DE602006021323T priority patent/DE602006021323D1/de
Priority to EP06777183A priority patent/EP1928886B1/en
Priority to DK06777183.2T priority patent/DK1928886T3/da
Priority to AU2006289281A priority patent/AU2006289281B2/en
Priority to AT06777183T priority patent/ATE505472T1/de
Priority to JP2008529564A priority patent/JP5121716B2/ja
Priority to EA200800784A priority patent/EA013909B1/ru
Application filed by SmithKline Beecham Corp filed Critical SmithKline Beecham Corp
Priority to SI200631047T priority patent/SI1928886T1/sl
Priority to CN2006800418603A priority patent/CN101305011B/zh
Priority to US12/065,923 priority patent/US7683056B2/en
Priority to PL06777183T priority patent/PL1928886T3/pl
Priority to CA2621564A priority patent/CA2621564C/en
Priority to KR1020087008441A priority patent/KR101292348B1/ko
Priority to NZ565983A priority patent/NZ565983A/en
Publication of WO2007028654A1 publication Critical patent/WO2007028654A1/en
Priority to IL189578A priority patent/IL189578A/en
Anticipated expiration legal-status Critical
Priority to NO20081728A priority patent/NO340921B1/no
Priority to US12/636,849 priority patent/US7919491B2/en
Priority to US13/032,740 priority patent/US8097618B2/en
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed 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
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic 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
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A61K31/5383—1,4-Oxazines, e.g. morpholine ortho- or peri-condensed with heterocyclic ring systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • 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
    • 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
    • A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
    • 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
    • A61P25/18—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
    • A61P25/20—Hypnotics; Sedatives
    • 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
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • 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
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • A61P25/32—Alcohol-abuse
    • 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
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • A61P25/34—Tobacco-abuse
    • 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
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • A61P25/36—Opioid-abuse
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems

Definitions

  • the present invention relates to novel nitrogen containing bicyclic derivatives having pharmacological activity, processes for their preparation, to compositions containing them and to their use in the treatment of psychotic disorders, in particular schizophrenia.
  • n 1
  • process (a) may be performed on the derivative wherein the hydroxyl group of R 2 is protected as an O-TBDMS derivative in a suitable solvent such as toluene, in the presence of a suitable catalyst such as bis-tri -tert- butylphosphine palladium, a suitable base such as aqueous sodium hydroxide and a suitable phase transfer catalyst such as aqueous hexadecyltrimethylammonium chloride at a temperature such as 80-95 0 C.
  • a suitable catalyst such as bis-tri -tert- butylphosphine palladium
  • a suitable base such as aqueous sodium hydroxide
  • a suitable phase transfer catalyst such as aqueous hexadecyltrimethylammonium chloride at a temperature such as 80-95 0 C.
  • This process can be followed by removal of theTBDMS protecting group using tetrabutylammonium fluoride in a suitable solvent such as THF, or hydroch
  • Step (ii) typically comprises a deprotection reaction, for example, when P 2 represents t- butoxy said deprotection reaction may typically comprise reacting a compound of formula (VIII) with a mixture of dichloromethane and trifluoroacetic acid, followed by purification on a SCX (Strong Cationic Exchange) silica cartridge and heating the basic methanolic fractions at a suitable temperature, such as 40 0 C.
  • a deprotection reaction for example, when P 2 represents t- butoxy said deprotection reaction may typically comprise reacting a compound of formula (VIII) with a mixture of dichloromethane and trifluoroacetic acid, followed by purification on a SCX (Strong Cationic Exchange) silica cartridge and heating the basic methanolic fractions at a suitable temperature, such as 40 0 C.
  • SCX Short Cationic Exchange
  • Step (iii) typically comprises reacting a compound of formula (XXVII) with borane tetrahydrofuran complex solution at a suitable temperature, such as 50°C, followed by treatment with an aqueous acid, such as hydrochloric acid, and purification on a SCX (Strong Cationic Exchange) silica cartridge.
  • a suitable temperature such as 50°C
  • an aqueous acid such as hydrochloric acid
  • the compounds of the invention may be used in combination with the following agents to treat or prevent autism: i) antipsychotics; ii) antidepressants; iii) anxiolytics; and iv) stimulants for example methylphenidate, amphetamine formulations and pemoline.
  • Antipsychotic drugs include Typical Antipsychotics (for example chlorpromazine, thioridazine, mesoridazine, fluphenazine, perphenazine, prochlorperazine, trifluoperazine, thiothixine, haloperidol, molindone and loxapine); and Atypical Antipsychotics (for example clozapine, olanzapine, risperidone, quetiapine, aripirazole, ziprasidone and amisulpride).
  • Typical Antipsychotics for example chlorpromazine, thioridazine, mesoridazine, fluphenazine, perphenazine, prochlorperazine, trifluoperazine, thiothixine, haloperidol, molindone and loxapine
  • Atypical Antipsychotics for example clozapine, olanzapine, risperidone, quetiapine,
  • Anxiolytics include benzodiazepines such as alprazolam and lorazepam.
  • Oral liquid preparations may be in the form of, for example, aqueous or oily suspension, solutions, emulsions, syrups or elixirs, or may be in the form of a dry product for reconstitution with water or other suitable vehicle before use.
  • Such liquid preparations may contain conventional additives such as suspending agents, emulsifying agents, non-aqueous vehicles (which may include edible oils), preservatives, and, if desired, conventional flavourings or colorants.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (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)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Psychiatry (AREA)
  • Addiction (AREA)
  • Epidemiology (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Gynecology & Obstetrics (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Hospice & Palliative Care (AREA)
  • Anesthesiology (AREA)
  • Psychology (AREA)
  • Nutrition Science (AREA)
  • Pulmonology (AREA)
  • Child & Adolescent Psychology (AREA)
  • Endocrinology (AREA)
  • Reproductive Health (AREA)
  • Obesity (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
PCT/EP2006/008845 2005-09-09 2006-09-07 Pyridine derivatives and their use in the treatment of psychotic disorders Ceased WO2007028654A1 (en)

Priority Applications (20)

Application Number Priority Date Filing Date Title
CA2621564A CA2621564C (en) 2005-09-09 2006-09-07 Pyridine derivatives and their use in the treatment of psychotic disorders
KR1020087008441A KR101292348B1 (ko) 2005-09-09 2006-09-07 피리딘 유도체 및 그의 정신병적 장애의 치료에 있어서의용도
NZ565983A NZ565983A (en) 2005-09-09 2006-09-07 Pyridine derivatives and their use in the treatment of psychotic disorders
CN2006800418603A CN101305011B (zh) 2005-09-09 2006-09-07 吡啶衍生物及其在治疗精神障碍中的用途
DE602006021323T DE602006021323D1 (de) 2005-09-09 2006-09-07 Pyridinderivate und ihre verwendung bei der behandlung psychotischer erkrankungen
EP06777183A EP1928886B1 (en) 2005-09-09 2006-09-07 Pyridine derivatives and their use in the treatment of psychotic disorders
DK06777183.2T DK1928886T3 (da) 2005-09-09 2006-09-07 Pyridin-derivater og deres anvendelse i behandlingen af psykotiske lidelser
AU2006289281A AU2006289281B2 (en) 2005-09-09 2006-09-07 Pyridine derivatives and their use in the treatment of psychotic disorders
AT06777183T ATE505472T1 (de) 2005-09-09 2006-09-07 Pyridinderivate und ihre verwendung bei der behandlung psychotischer erkrankungen
JP2008529564A JP5121716B2 (ja) 2005-09-09 2006-09-07 ピリジン誘導体および精神異常の処置におけるそれらの使用
EA200800784A EA013909B1 (ru) 2005-09-09 2006-09-07 Пиридиновые производные и их применение для лечения психотических расстройств
BRPI0615787A BRPI0615787B8 (pt) 2005-09-09 2006-09-07 derivados de piridina e seu uso no tratamento de distúrbios psicóticos
SI200631047T SI1928886T1 (sl) 2005-09-09 2006-09-07 Derivati piridina in njihova uporaba pri zdravljenju psihotiäśnih motenj
HR20110457T HRP20110457T1 (hr) 2005-09-09 2006-09-07 Derivati piridina i njihova upotreba u liječenju psihotičnih poremećaja
US12/065,923 US7683056B2 (en) 2005-09-09 2006-09-07 Pyridine derivatives and their use in the treatment of psychotic disorders
PL06777183T PL1928886T3 (pl) 2005-09-09 2006-09-07 Pochodne pirydyny i ich zastosowanie w leczeniu zaburzeń psychotycznych
IL189578A IL189578A (en) 2005-09-09 2008-02-18 Pyridine derivatives, pharmaceutical compounds containing them, and their use in the preparation of drugs for the treatment of cns diseases
NO20081728A NO340921B1 (no) 2005-09-09 2008-04-07 Pyridinderivater og deres anvendelse i behandlingen av psykotiske forstyrrelser
US12/636,849 US7919491B2 (en) 2005-09-09 2009-12-14 Pyridine derivatives and their use in the treatment of psychotic disorders
US13/032,740 US8097618B2 (en) 2005-09-09 2011-02-23 Pyridine derivatives and their use in the treatment of psychotic disorders

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GB0611153.8 2005-06-06
GB0518472.6 2005-09-09
GB0518472A GB0518472D0 (en) 2005-09-09 2005-09-09 Novel compounds
GB0611153A GB0611153D0 (en) 2006-06-06 2006-06-06 Novel compounds

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US12/065,923 A-371-Of-International US7683056B2 (en) 2005-09-09 2006-09-07 Pyridine derivatives and their use in the treatment of psychotic disorders
US12/636,849 Continuation US7919491B2 (en) 2005-09-09 2009-12-14 Pyridine derivatives and their use in the treatment of psychotic disorders

Publications (1)

Publication Number Publication Date
WO2007028654A1 true WO2007028654A1 (en) 2007-03-15

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PCT/EP2006/008845 Ceased WO2007028654A1 (en) 2005-09-09 2006-09-07 Pyridine derivatives and their use in the treatment of psychotic disorders

Country Status (28)

Country Link
US (3) US7683056B2 (enExample)
EP (2) EP2336136A1 (enExample)
JP (1) JP5121716B2 (enExample)
KR (1) KR101292348B1 (enExample)
CN (1) CN101305011B (enExample)
AR (1) AR058805A1 (enExample)
AT (1) ATE505472T1 (enExample)
AU (1) AU2006289281B2 (enExample)
BR (1) BRPI0615787B8 (enExample)
CA (1) CA2621564C (enExample)
CR (1) CR9847A (enExample)
CY (1) CY1111907T1 (enExample)
DE (1) DE602006021323D1 (enExample)
DK (1) DK1928886T3 (enExample)
EA (1) EA013909B1 (enExample)
HR (1) HRP20110457T1 (enExample)
IL (1) IL189578A (enExample)
JO (1) JO2722B1 (enExample)
MA (1) MA29780B1 (enExample)
MY (1) MY145713A (enExample)
NO (1) NO340921B1 (enExample)
NZ (1) NZ565983A (enExample)
PE (1) PE20070614A1 (enExample)
PL (1) PL1928886T3 (enExample)
PT (1) PT1928886E (enExample)
SI (1) SI1928886T1 (enExample)
TW (1) TWI378101B (enExample)
WO (1) WO2007028654A1 (enExample)

Cited By (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007039123A3 (en) * 2005-09-22 2007-06-21 Smithkline Beecham Corp Combination therapy comprising an nk-3 antagonist and an antipsychotic agent
WO2008090117A1 (en) 2007-01-24 2008-07-31 Glaxo Group Limited Pharmaceutical compositions comprising 3, 5-diamin0-6- (2, 3-dichl0phenyl) -l, 2, 4-triazine or r (-) -2, 4-diamino-5- (2, 3-dichlorophenyl) -6-fluoromethyl pyrimidine and an nk1
WO2009119528A1 (ja) * 2008-03-24 2009-10-01 武田薬品工業株式会社 複素環化合物
WO2009138393A1 (en) * 2008-05-14 2009-11-19 Glaxo Wellcome Manufacturing Pte Ltd 5-[5-[2-(3,5-bis(trifluoromethyl)phenyl)-2-methylpropanoylmethylamino]-4-(4-fluoro-2-methylphenyl)]-2-pyridinyl-2-alkyl-prolinamide as nk1 receptor antagonists
US7659268B2 (en) 2005-11-08 2010-02-09 Vertex Pharmaceuticals Incorporated Modulators of ATP-binding cassette transporters
WO2010015626A1 (en) * 2008-08-05 2010-02-11 Smithkline Beecham Corporation Crystalline forms of a pyridine derivative
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