CA2646081C - Crystalline forms and processes for the preparation of phenyl-pyrazoles useful as modulators of the 5-ht2a serotonin receptor - Google Patents
Crystalline forms and processes for the preparation of phenyl-pyrazoles useful as modulators of the 5-ht2a serotonin receptor Download PDFInfo
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- CA2646081C CA2646081C CA2646081A CA2646081A CA2646081C CA 2646081 C CA2646081 C CA 2646081C CA 2646081 A CA2646081 A CA 2646081A CA 2646081 A CA2646081 A CA 2646081A CA 2646081 C CA2646081 C CA 2646081C
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- compound
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- salt
- alkyl
- crystalline form
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- 238000000034 method Methods 0.000 title claims abstract description 166
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 42
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- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
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- 230000008719 thickening Effects 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- 150000007944 thiolates Chemical class 0.000 description 1
- 125000000464 thioxo group Chemical group S=* 0.000 description 1
- RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
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Landscapes
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- Emergency Medicine (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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| US60/921,318 | 2007-04-02 | ||
| PCT/US2007/011810 WO2007136689A2 (en) | 2006-05-18 | 2007-05-17 | Crystalline forms and processes for the preparation of phenyl-pyrazoles useful as modulators of the 5-ht2a serotonin receptor |
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| CN1826322B (zh) | 2003-07-22 | 2012-04-18 | 艾尼纳制药公司 | 用于预防和治疗相关病症而作为5-ht2a血清素受体调节剂的二芳基和芳基杂芳基脲衍生物 |
| SA05260357B1 (ar) | 2004-11-19 | 2008-09-08 | ارينا فارماسيتو تيكالز ، أنك | مشتقات 3_فينيل_بيرازول كمعدلات لمستقبل سيروتينين 5_ht2a مفيدة في علاج الاضطرابات المتعلقه به |
| JP5389642B2 (ja) | 2006-05-18 | 2014-01-15 | アリーナ ファーマシューティカルズ， インコーポレイテッド | ５−ｈｔ２ａセロトニンレセプターに関連する障害の処置に有用な５−ｈｔ２ａセロトニンレセプターのモジュレーターとしての３−ピラゾリル−ベンズアミド−４−エーテル、二級アミンおよびその誘導体 |
| NZ571829A (en) | 2006-05-18 | 2011-10-28 | Arena Pharm Inc | Crystalline forms and processes for the preparation of phenyl-pyrazoles useful as modulators of the 5-HT2A serotonin receptor |
| WO2007136703A1 (en) | 2006-05-18 | 2007-11-29 | Arena Pharmaceuticals, Inc. | Primary amines and derivatives thereof as modulators of the 5-ht2a serotonin receptor useful for the treatment of disorders related thereto |
| TWI415845B (zh) | 2006-10-03 | 2013-11-21 | Arena Pharm Inc | 用於治療與５-ｈｔ2ａ血清素受體相關聯病症之作為５-ｈｔ2ａ血清素受體之調節劑的吡唑衍生物 |
| JP5393677B2 (ja) | 2007-08-15 | 2014-01-22 | アリーナ ファーマシューティカルズ， インコーポレイテッド | ５−ＨＴ２Ａセロトニン受容体に関連した障害の治療のための５−ＨＴ２Ａセロトニン受容体のモジュレーターとしてのイミダゾ［１，２−ａ］ピリジン誘導体 |
| WO2009123714A2 (en) | 2008-04-02 | 2009-10-08 | Arena Pharmaceuticals, Inc. | Processes for the preparation of pyrazole derivatives useful as modulators of the 5-ht2a serotonin receptor |
| WO2010062321A1 (en) | 2008-10-28 | 2010-06-03 | 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 |
| US9034911B2 (en) | 2008-10-28 | 2015-05-19 | Arena Pharmaceuticals, Inc. | Composition of a 5-HT2A serotonin receptor modulator useful for the treatment of disorders related thereto |
| WO2011075596A1 (en) | 2009-12-18 | 2011-06-23 | Arena Pharmaceuticals, Inc. | Crystalline forms of certain 3-phenyl-pyrazole derivatives as modulators of the 5-ht2a serotonin receptor useful for the treatment of disorders related thereto |
| EP2563759B1 (en) * | 2010-04-27 | 2022-04-06 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| EP4119141A1 (en) | 2015-06-12 | 2023-01-18 | Axovant Sciences GmbH | Nelotanserin for the prophylaxis and treatment of rem sleep behavior disorder |
| WO2017011767A2 (en) | 2015-07-15 | 2017-01-19 | Axovant Sciences Ltd. | 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 |
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- 2007-05-17 JP JP2009511063A patent/JP5286254B2/ja not_active Expired - Fee Related
- 2007-05-17 ES ES07794969.1T patent/ES2543718T3/es active Active
- 2007-05-17 EA EA200870544A patent/EA016675B1/ru not_active IP Right Cessation
- 2007-05-17 EP EP12162245A patent/EP2527329A1/en not_active Withdrawn
- 2007-05-17 CN CN2012102989512A patent/CN102827081A/zh active Pending
- 2007-05-17 WO PCT/US2007/011810 patent/WO2007136689A2/en not_active Ceased
- 2007-05-17 KR KR1020087028020A patent/KR101514846B1/ko not_active Expired - Fee Related
- 2007-05-17 US US12/301,212 patent/US8481535B2/en active Active
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- 2007-05-17 MY MYPI20084456A patent/MY154962A/en unknown
- 2007-05-17 SG SG201103381-8A patent/SG171681A1/en unknown
- 2007-05-17 BR BRPI0712030-3A patent/BRPI0712030A2/pt not_active Application Discontinuation
- 2007-05-17 MX MX2013007579A patent/MX349156B/es unknown
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| US20130296321A1 (en) | 2013-11-07 |
| EP2018372B1 (en) | 2015-05-13 |
| HK1121453A1 (en) | 2009-04-24 |
| EA200870544A1 (ru) | 2009-06-30 |
| SG171681A1 (en) | 2011-06-29 |
| IL193822A (en) | 2015-11-30 |
| NZ571829A (en) | 2011-10-28 |
| BRPI0712030A2 (pt) | 2012-01-03 |
| US9199940B2 (en) | 2015-12-01 |
| ES2543718T3 (es) | 2015-08-21 |
| AU2007254255A1 (en) | 2007-11-29 |
| KR20090009244A (ko) | 2009-01-22 |
| MX2008014622A (es) | 2008-11-28 |
| MX349156B (es) | 2017-07-14 |
| US9783502B2 (en) | 2017-10-10 |
| EP2527329A1 (en) | 2012-11-28 |
| US20160272591A1 (en) | 2016-09-22 |
| NZ594353A (en) | 2013-02-22 |
| IL222340A (en) | 2014-05-28 |
| US20100234380A1 (en) | 2010-09-16 |
| CN102827081A (zh) | 2012-12-19 |
| US20180186748A1 (en) | 2018-07-05 |
| CA2646081A1 (en) | 2007-11-29 |
| US8481535B2 (en) | 2013-07-09 |
| WO2007136689A3 (en) | 2008-01-10 |
| EA016675B1 (ru) | 2012-06-29 |
| JP5286254B2 (ja) | 2013-09-11 |
| MY154962A (en) | 2015-08-28 |
| JP2009537544A (ja) | 2009-10-29 |
| AU2007254255B2 (en) | 2013-03-07 |
| EP2018372A2 (en) | 2009-01-28 |
| WO2007136689A2 (en) | 2007-11-29 |
| KR101514846B1 (ko) | 2015-04-23 |
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