WO2005040124A1 - A polymorphic form of 3-phenylsulfonyl -8-piperazin-1-yl-quinoline - Google Patents
A polymorphic form of 3-phenylsulfonyl -8-piperazin-1-yl-quinoline Download PDFInfo
- Publication number
- WO2005040124A1 WO2005040124A1 PCT/EP2004/010843 EP2004010843W WO2005040124A1 WO 2005040124 A1 WO2005040124 A1 WO 2005040124A1 EP 2004010843 W EP2004010843 W EP 2004010843W WO 2005040124 A1 WO2005040124 A1 WO 2005040124A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- polymorph according
- schizophrenia
- piperazin
- quinoline
- phenylsulfonyl
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
- C07D215/40—Nitrogen atoms attached in position 8
-
- 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
- A61P25/18—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
- A61P25/28—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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
Definitions
- This invention relates to a novel compound having pharmacological activity, to processes for its preparation, to compositions containing it and to its use in the treatment of CNS and other disorders.
- WO 2003/080580 (Glaxo Group Limited) describes the preparation of 3-phenylsulfonyl- 8-piperazin-1-yl-quinoline (Example 16) in addition to two polymorphic forms of 3- phenylsulfonyl-8-piperazin-1-yl-quinoline (Form I; Example 51 and Form II; Example 52).
- 3-Phenylsulfonyl-8-piperazin-1-yl-quinoline is disclosed in WO 2003/080580 as having affinity for the 5-HT 6 receptor and is claimed to be useful in the treatment of CNS and other disorders.
- 3-pheny(sulfonyl-8-piperazin-1-yl-quinoline exists in a further polymorphic form which is primarily characterised in that it possesses a higher melting point than Forms I and II.
- This further polymorphic form of 3-phenylsulfonyl-8-piperazin- 1-yl-quinoline is referred to as Form III.
- the present invention provides 3-phenylsulfonyl-8-piperazin-1-yl-quinoline, suitably as characterised by data provided by at least one of the following: infrared, Raman, X-ray powder diffraction or nuclear magnetic resonance and melting point data as provided herein, including partial spectral data provided herein.
- one aspect of the present invention provides a polymorphic form of 3- phenylsulfonyl-8-piperazin-1-yl-quinoline, characterised in that it provides:
- the polymorph of the present invention provides an infrared spectrum substantially in accordance with Figure 1. In one preferred aspect, the polymorph of the present invention provides a Raman spectrum substantially in accordance with Figure 2.
- the polymorph of the present invention provides an X-ray powder diffraction (XRPD) pattern which gives calculated lattice spacings at 10.29, 10.76, 11.94, 14.33, 14.61 , 14.93, 16.02, 16.80, 17.47, 17.92, 19.13, 19.55, 19.84, 20.33, 21.16, 21.36, 23.33, 23.96, 24.44, 24.67, 25.51 , 26.12, 27.13, 27.77, 28.06, 28.35, 29.23, 29.46, 30.06, 30.35, 31.27, 32.35, 32.66, 33.08, 33.77, 34.49, 35.18, 36.42, 37.34, 38.39 and 39.51°.
- XRPD X-ray powder diffraction
- the polymorph of the present invention provides an X-ray powder diffraction (XRPD) pattern substantially in accordance with Figure 3.
- XRPD X-ray powder diffraction
- the present invention encompasses the polymorph isolated in pure form or when admixed with other materials, for example the known forms of 3-phenylsulfonyl- ⁇ - piperazin-1-yl-quinoline or any other material.
- the polymorph in isolated form. In a further aspect there is provided the polymorph in pure form. In yet a further aspect there is provided the polymorph in crystalline form. Most preferably, the polymorph is provided in pure form.
- 'Isolated in pure form' refers to 3-phenylsulfonyl-8-piperazin-1-yl-quinoline Form III present in an amount of preferably >75%, more preferably >90%, particularly >95%, especially >99% relative to other compounds or polymorphs of 3-phenylsulfonyl-8- piperazin-1-yl-quinoline which may be present in an isolated sample.
- the compound of the present invention has affinity for the 5-HT 6 receptor and is believed to be of potential use in the treatment of certain CNS disorders such as anxiety, depression, epilepsy, obsessive compulsive disorders, migraine, cognitive memory disorders (e.g. Alzheimers disease, age related cognitive decline and mild cognitive impairment), Parkinsons Disease, ADHD (Attention Deficit Disorder/Hyperactivity Syndrome), sleep disorders (including disturbances of Circadian rhythm), feeding disorders such as anorexia and bulimia, panic attacks, withdrawal from drug abuse such as ***e, ethanpl, nicotine and benzodiazepines, schizophrenia (in particular cognitive deficits of schizophrenia), stroke and also disorders associated with spinal trauma and/or head injury such as hydrocephalus.
- CNS disorders such as anxiety, depression, epilepsy, obsessive compulsive disorders, migraine, cognitive memory disorders (e.g. Alzheimers disease, age related cognitive decline and mild cognitive impairment), Parkinsons Disease, ADHD (Attention Deficit Disorder/Hyperactivity Syndrome), sleep disorders (including disturbances of Circa
- the compound of the invention is also expected to be of use in the treatment of certain Gl (gastrointestinal) disorders such as IBS (Irritable Bowel Syndrome).
- the compound of the invention is also expected to be of use in the treatment of obesity.
- the invention also provides 3-phenylsulfonyl-8-piperazin-1-yl-quinoline (Form III), for use as a therapeutic substance, in particular in the treatment or prophylaxis of the above disorders.
- the invention provides for 3-phenylsulfonyl-8-piperazin-1- yl-quinoline (Form III), for use in the treatment of depression, anxiety, Alzheimers disease, age related cognitive decline, ADHD, obesity, mild cognitive impairment, schizophrenia, cognitive deficits in schizophrenia and stroke.
- the invention further provides a method of treatment or prophylaxis of the above disorders, in mammals including humans, which comprises administering to the sufferer a therapeutically effective amount of 3-phenylsulfonyl-8-piperazin-1-yl-quinoline (Form III).
- the invention provides the use of 3-phenylsulfonyl-8-piperazin-1-yl- quinoline (Form III) in the manufacture of a medicament for use in the treatment or prophylaxis of the above disorders.
- 5-HT 6 antagonists have the potential to be capable of increasing basal and learning- induced polysialylated neuron cell frequency in brain regions such as the rat medial temporal lobe and associated hippocampus, as described in WO 2003/066056.
- a method of promoting neuronal growth within the central nervous system of a mammal which comprises the step of administering 3-phenylsulfonyl-8-piperazin-1-yl-quinoline (Form III).
- the present invention also provides a pharmaceutical composition, which comprises 3-phenylsulfonyl-8-piperazin-1-yl-quinoline (Form III), and a pharmaceutically acceptable carrier.
- a pharmaceutical composition which comprises 3-phenylsulfonyl-8-piperazin-1-yl-quinoline (Form III), and a pharmaceutically acceptable carrier.
- a pharmaceutical composition of the invention which may be prepared by admixture, suitably at ambient temperature and atmospheric pressure, is usually adapted for oral, parenteral or rectal administration and, as such, may be in the form of tablets, capsules, oral liquid preparations, powders, granules, lozenges, reconstitutable powders, injectable or infusable solutions or suspensions or suppositories. Orally administrable compositions are generally preferred.
- Tablets and capsules for oral administration may be in unit dose form, and may contain conventional excipients, such as binding agents, fillers, tabletting lubricants, disintegrants and acceptable wetting agents.
- the tablets may be coated according to methods well known in normal pharmaceutical practice.
- 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 colourants.
- fluid unit dosage forms are prepared utilising a compound of the invention or pharmaceutically acceptable salt thereof and a sterile vehicle.
- the compound depending on the vehicle and concentration used, can be either suspended or dissolved in the vehicle.
- the compound can be dissolved for injection and filter sterilised before filling into a suitable vial or ampoule and sealing.
- adjuvants such as a local anaesthetic, preservatives and buffering agents are dissolved in the vehicle.
- the composition can be frozen after filling into the vial and the water removed under vacuum.
- Parenteral suspensions are prepared in substantially the same manner, except that the compound is suspended in the vehicle instead of being dissolved, and sterilization cannot be accomplished by filtration.
- the compound can be sterilised by exposure to ethylene oxide before suspension in a sterile vehicle.
- a surfactant or wetting agent is included in the composition to facilitate uniform distribution of the compound.
- composition may contain from 0.1% to 99% by weight, preferably from 10 to 60% by weight, of the active material, depending on the method of administration.
- suitable unit doses may be 0.05 to 1000 mg, more suitably 0.05 to 200 mg, for example 20 to 40 mg; and such unit doses will preferably be administered once a day, although administration more than once a day may be required; and such therapy may extend for a number of weeks or months.
- 3-Phenylsulfonyl-8-piperazin-1-yl-quinoline (D5) (10g) was dissolved in ethanol (80ml) with warming to 70°C. The resultant solution was then treated with charcoal (1g), filtered, and the filter bed rinsed with ethanol (20ml). The combined filtrate was adjusted to 54°C, then cooled to 50 °C over 15 minutes. The solution was seeded with 3- phenylsulfonyl-8-piperazin-1-yl-quinoline (Form III) (10mg), cooled to 35°C over 30 minutes, held for 1 hour, then cooled to 20 °C over 30 minutes, and stirred for a further 1 hour 15 minutes. The product was collected by filtration, washed with cold ethanol, (2 x 10ml;)and dried in vacuo at 40°C to give the title compound, 6.64g, 66.4%. Melting point 188°C.
- 3-Phenylsulfonyl-8-piperazin-1-yl-quinoline (D5) (10g) was dissolved in ethanol (80ml) with warming to 72°C.
- the resultant solution was then pumped through a Cuno R55SP filter into a second vessel (pre-heated to 55°C) via a sinter funnel.
- the original flask and the Cuno filter were washed with ethanol (20ml).
- the combined filtrate was heated to 72°C to redissolve the material, then adjusted to 50°C.
- Characterising data recorded for Example 1 The infrared spectrum of the solid product was recorded using a Nicolet Avatar 360 FT- IR spectrometer fitted with a universal ATR accessory.
- the FT-IR spectrum ( Figure 1) shows bands at: 724, 758, 777, 804, 818, 838, 856, 905, 918, 948, 1023, 1055, 1081 , 1092, 1118, 1136, 1153, 1178, 1244, 1302, 1318, 1365, 1378, 1403, 1444, 1471 , 1490, 1569, 1584, 1603 and 2819 cm "1 .
- FT-Raman spectra of samples in glass tubes were acquired using a ThermNicolet 960 E.S.P. spectrometer. Excitation at 1064 nm was provided by a Nd:YVO 4 laser with a power of 400 mW at the sample position. 1200 scans were recorded at 4 cm "1 resolution.
- the FT-Raman spectrum ( Figure 2) shows bands at 159, 184, 214, 241 , 285, 304, 318, 429, 545, 558, 614, 706, 724, 803, 856, 1000, 1023, 1080, 1093, 1136, 1152, 1233, 1243, 1317, 1343, 1364, 1378, 1403, 1446, 1569, 1584, 1602, 3050 and 3073 cm “1 .
- the X-Ray Powder Diffractogram pattern of the solid product ( Figure 3) was recorded using the following acquisition conditions: Unground material was packed into top-filled Si cups. Powder patterns were obtained using a Bruker D8 Advance X-Ray powder diffractometer configured with a Cu anode (40 kV, 40 mA), variable divergence slit, primary and secondary Soller slits, and a position sensitive detector. Data were acquired over the range 2 - 40 degrees 2-theta using a step size of 0.0145 degrees 2- theta (1 s per step). Samples were rotated during data collection.
- Characteristic 2 ⁇ XRPD angles are 10.29, 10.76, 11.94, 14.33, 14.61 , 14.93, 16.02, 16.80, 17.47, 17.92, 19.13, 19.55, 19.84, 20.33, 21.16, 21.36, 23.33, 23.96, 24.44, 24.67, 25.51, 26.12, 27.13, 27.77, 28.06, 28.35, 29.23, 29.46, 30.06, 30.35, 31.27, 32.35, 32.66, 33.08, 33.77, 34.49, 35.18, 36.42, 37.34, 38.39 and 39.51°.
- Figure 1 shows the Infrared spectrum obtained for 3-phenylsulfonyl-8-piperazin-1-yl- quinoline (Form III).
- Figure 2 shows the Raman spectrum obtained for 3-phenylsulfonyl-8-piperazin-1-yl- quinoline (Form III).
- Figure 3 shows the X-Ray Powder Diffractogram obtained for 3-phenylsulfonyl-8- piperazin-1-yl-quinoline (Form III).
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Diabetes (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Child & Adolescent Psychology (AREA)
- Obesity (AREA)
- Hospice & Palliative Care (AREA)
- Hematology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
Description
Claims
Priority Applications (16)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU2004283805A AU2004283805A1 (en) | 2003-09-26 | 2004-09-23 | A polymorphic form of 3-phenylsulfonyl -8-piperazin-1-yl-quinoline |
DE602004010410T DE602004010410T2 (en) | 2003-09-26 | 2004-09-23 | POLYMORPHIC FORM OF 3-PHENYLSULFONYL-8-PIPERAZINE-1-YL-CHINOLINE |
MXPA06003375A MXPA06003375A (en) | 2003-09-26 | 2004-09-23 | A polymorphic form of 3-phenylsulfonyl -8-piperazin-1-yl-quinoline. |
DK04765655T DK1667975T3 (en) | 2003-09-26 | 2004-09-23 | A polymorphic form of 3-phenylsulfonyl-8-piperazin-1-yl-quinoline |
US10/572,670 US20070032504A1 (en) | 2003-09-26 | 2004-09-23 | Polymorphic form of 3-phenylsulfonyl -8-piperazin-1-yl-quinoline |
CA002540022A CA2540022A1 (en) | 2003-09-26 | 2004-09-23 | A polymorphic form of 3-phenylsulfonyl-8-piperazin-1-yl-quinoline |
SI200430610T SI1667975T1 (en) | 2003-09-26 | 2004-09-23 | A polymorphic form of 3-phenylsulfonyl-8-piperazin-1-yl-quinoline |
EP04765655A EP1667975B1 (en) | 2003-09-26 | 2004-09-23 | A polymorphic form of 3-phenylsulfonyl-8-piperazin-1-yl-quinoline |
PL04765655T PL1667975T3 (en) | 2003-09-26 | 2004-09-23 | A polymorphic form of 3-phenylsulfonyl-8-piperazin-1-yl-quinoline |
JP2006527373A JP2007506702A (en) | 2003-09-26 | 2004-09-23 | Polymorph of 3-phenylsulfonyl-8-piperazin-1-yl-quinoline |
BRPI0414678-6A BRPI0414678A (en) | 2003-09-26 | 2004-09-23 | polymorphic form of 3-phenyl sulfonyl-8-piperazin-1-yl quinoline |
IL174213A IL174213A0 (en) | 2003-09-26 | 2006-03-09 | A polymorphic form of 3-phenylsulfonyl-8-piperazin-1-yl-quinoline |
IS8399A IS8399A (en) | 2003-09-26 | 2006-04-05 | Form of polyphenyl 3-phenylsulfonyl-8-piperazin-1-yl-quinoline |
NO20061791A NO20061791L (en) | 2003-09-26 | 2006-04-24 | Polymorphic form of 3-phenylsulfonyl-8-piperazin-1-yl-quinoline |
HK06113097A HK1094190A1 (en) | 2003-09-26 | 2006-11-29 | a polymorphic form of 3-phenylsulfonyl-8-piperazin-1-yl-quinoline |
HR20080055T HRP20080055T3 (en) | 2003-09-26 | 2008-02-04 | A polymorphic form of 3-phenylsulfonyl-8-piperazin-1-yl-quinoline |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB0322629.7 | 2003-09-26 | ||
GBGB0322629.7A GB0322629D0 (en) | 2003-09-26 | 2003-09-26 | Novel compound |
Publications (1)
Publication Number | Publication Date |
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WO2005040124A1 true WO2005040124A1 (en) | 2005-05-06 |
Family
ID=29286934
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2004/010843 WO2005040124A1 (en) | 2003-09-26 | 2004-09-23 | A polymorphic form of 3-phenylsulfonyl -8-piperazin-1-yl-quinoline |
Country Status (24)
Country | Link |
---|---|
US (1) | US20070032504A1 (en) |
EP (1) | EP1667975B1 (en) |
JP (1) | JP2007506702A (en) |
CN (1) | CN1856471A (en) |
AU (1) | AU2004283805A1 (en) |
BR (1) | BRPI0414678A (en) |
CA (1) | CA2540022A1 (en) |
CO (1) | CO5680402A2 (en) |
DE (1) | DE602004010410T2 (en) |
DK (1) | DK1667975T3 (en) |
ES (1) | ES2297465T3 (en) |
GB (1) | GB0322629D0 (en) |
HK (1) | HK1094190A1 (en) |
HR (1) | HRP20080055T3 (en) |
IL (1) | IL174213A0 (en) |
IS (1) | IS8399A (en) |
MA (1) | MA28093A1 (en) |
MX (1) | MXPA06003375A (en) |
NO (1) | NO20061791L (en) |
PL (1) | PL1667975T3 (en) |
PT (1) | PT1667975E (en) |
RU (1) | RU2355681C2 (en) |
WO (1) | WO2005040124A1 (en) |
ZA (1) | ZA200601453B (en) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007039238A1 (en) * | 2005-09-28 | 2007-04-12 | Glaxo Group Limited | Novel chemical process for the synthesis of quinoline compounds |
US7547701B2 (en) | 2003-09-18 | 2009-06-16 | Virobay, Inc. | Haloalkyl containing compounds as cysteine protease inhibitors |
WO2009074607A1 (en) * | 2007-12-12 | 2009-06-18 | Glaxo Group Limited | Combinations comprising 3-phenylsulfonyl-8-piperazinyl-1yl-quinoline |
US7728142B2 (en) | 2005-06-02 | 2010-06-01 | Hoffmann-La Roche Inc. | 3-methanesulfonylquinolines as GABAB enhancers |
US9745270B2 (en) | 2008-10-28 | 2017-08-29 | 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 |
US9775829B2 (en) | 2003-07-22 | 2017-10-03 | Arena Pharmaceuticals, Inc. | Diaryl and arylheteroaryl urea derivatives as modulators of the 5-HT2A serotonin receptor useful for the prophylaxis and treatment of disorders related thereto |
US10022355B2 (en) | 2015-06-12 | 2018-07-17 | Axovant Sciences Gmbh | Diaryl and arylheteroaryl urea derivatives as modulators of the 5-HT2A serotonin receptor useful for the prophylaxis and treatment of REM sleep behavior disorder |
US10034859B2 (en) | 2015-07-15 | 2018-07-31 | Axovant Sciences Gmbh | Diaryl and arylheteroaryl urea derivatives as modulators of the 5-HT2A serotonin receptor useful for the prophylaxis and treatment of hallucinations associated with a neurodegenerative disease |
US10059691B2 (en) | 2008-04-02 | 2018-08-28 | Arena Pharmaceuticals, Inc. | Processes for the preparation of pyrazole derivatives useful as modulators of the 5-HT2A serotonin receptor |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2003080580A2 (en) * | 2002-03-27 | 2003-10-02 | Glaxo Group Limited | Quinoline derivatives and their use as 5-ht6 ligands |
JP2010521516A (en) * | 2007-03-21 | 2010-06-24 | グラクソ グループ リミテッド | Use of quinoline derivatives in the treatment of pain and irritable bowel syndrome |
CN108290842B (en) * | 2016-05-27 | 2021-04-06 | 深圳市塔吉瑞生物医药有限公司 | Substituted quinoline compound and pharmaceutical composition thereof |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2003080580A2 (en) * | 2002-03-27 | 2003-10-02 | Glaxo Group Limited | Quinoline derivatives and their use as 5-ht6 ligands |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
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GB9818916D0 (en) * | 1998-08-28 | 1998-10-21 | Smithkline Beecham Plc | Use |
GB0321473D0 (en) * | 2003-09-12 | 2003-10-15 | Glaxo Group Ltd | Novel compounds |
-
2003
- 2003-09-26 PT PT04765655T patent/PT1667975E/en unknown
- 2003-09-26 GB GBGB0322629.7A patent/GB0322629D0/en not_active Ceased
-
2004
- 2004-09-23 BR BRPI0414678-6A patent/BRPI0414678A/en not_active IP Right Cessation
- 2004-09-23 EP EP04765655A patent/EP1667975B1/en active Active
- 2004-09-23 DK DK04765655T patent/DK1667975T3/en active
- 2004-09-23 JP JP2006527373A patent/JP2007506702A/en not_active Withdrawn
- 2004-09-23 RU RU2006114024/04A patent/RU2355681C2/en active
- 2004-09-23 CN CNA2004800275278A patent/CN1856471A/en active Pending
- 2004-09-23 CA CA002540022A patent/CA2540022A1/en not_active Abandoned
- 2004-09-23 DE DE602004010410T patent/DE602004010410T2/en not_active Expired - Fee Related
- 2004-09-23 MX MXPA06003375A patent/MXPA06003375A/en active IP Right Grant
- 2004-09-23 WO PCT/EP2004/010843 patent/WO2005040124A1/en active IP Right Grant
- 2004-09-23 ES ES04765655T patent/ES2297465T3/en active Active
- 2004-09-23 US US10/572,670 patent/US20070032504A1/en not_active Abandoned
- 2004-09-23 PL PL04765655T patent/PL1667975T3/en unknown
- 2004-09-23 AU AU2004283805A patent/AU2004283805A1/en not_active Abandoned
-
2006
- 2006-02-20 ZA ZA200601453A patent/ZA200601453B/en unknown
- 2006-03-09 IL IL174213A patent/IL174213A0/en unknown
- 2006-03-27 CO CO06030123A patent/CO5680402A2/en not_active Application Discontinuation
- 2006-04-05 IS IS8399A patent/IS8399A/en unknown
- 2006-04-13 MA MA28933A patent/MA28093A1/en unknown
- 2006-04-24 NO NO20061791A patent/NO20061791L/en not_active Application Discontinuation
- 2006-11-29 HK HK06113097A patent/HK1094190A1/en not_active IP Right Cessation
-
2008
- 2008-02-04 HR HR20080055T patent/HRP20080055T3/en unknown
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2003080580A2 (en) * | 2002-03-27 | 2003-10-02 | Glaxo Group Limited | Quinoline derivatives and their use as 5-ht6 ligands |
Cited By (14)
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US20070032504A1 (en) | 2007-02-08 |
NO20061791L (en) | 2006-04-24 |
RU2355681C2 (en) | 2009-05-20 |
HRP20080055T3 (en) | 2008-02-29 |
IL174213A0 (en) | 2006-08-01 |
DE602004010410D1 (en) | 2008-01-10 |
JP2007506702A (en) | 2007-03-22 |
PL1667975T3 (en) | 2008-04-30 |
EP1667975B1 (en) | 2007-11-28 |
MXPA06003375A (en) | 2006-06-08 |
RU2006114024A (en) | 2007-11-10 |
CA2540022A1 (en) | 2005-05-06 |
IS8399A (en) | 2006-04-05 |
BRPI0414678A (en) | 2006-11-28 |
HK1094190A1 (en) | 2007-03-23 |
DE602004010410T2 (en) | 2008-10-16 |
AU2004283805A1 (en) | 2005-05-06 |
MA28093A1 (en) | 2006-08-01 |
CN1856471A (en) | 2006-11-01 |
CO5680402A2 (en) | 2006-09-29 |
GB0322629D0 (en) | 2003-10-29 |
PT1667975E (en) | 2008-02-29 |
ES2297465T3 (en) | 2008-05-01 |
ZA200601453B (en) | 2007-04-25 |
DK1667975T3 (en) | 2008-04-14 |
EP1667975A1 (en) | 2006-06-14 |
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