JP2009537544A5 - - Google Patents
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- JP2009537544A5 JP2009537544A5 JP2009511063A JP2009511063A JP2009537544A5 JP 2009537544 A5 JP2009537544 A5 JP 2009537544A5 JP 2009511063 A JP2009511063 A JP 2009511063A JP 2009511063 A JP2009511063 A JP 2009511063A JP 2009537544 A5 JP2009537544 A5 JP 2009537544A5
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- Prior art keywords
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- formula
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- 238000000034 method Methods 0.000 claims description 135
- 150000001875 compounds Chemical class 0.000 claims description 106
- 125000000217 alkyl group Chemical group 0.000 claims description 73
- 150000003839 salts Chemical group 0.000 claims description 40
- 125000001188 haloalkyl group Chemical group 0.000 claims description 38
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 32
- 208000035475 disorder Diseases 0.000 claims description 32
- 125000005843 halogen group Chemical group 0.000 claims description 30
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 28
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 28
- 125000003545 alkoxy group Chemical group 0.000 claims description 26
- 208000028017 Psychotic disease Diseases 0.000 claims description 24
- 125000003342 alkenyl group Chemical group 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 24
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 24
- 125000000304 alkynyl group Chemical group 0.000 claims description 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 201000000980 schizophrenia Diseases 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 12
- 125000001153 fluoro group Chemical group F* 0.000 claims description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
- 208000010110 spontaneous platelet aggregation Diseases 0.000 claims description 12
- 208000024891 symptom Diseases 0.000 claims description 12
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 9
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 9
- 150000003003 phosphines Chemical class 0.000 claims description 9
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 9
- 238000002560 therapeutic procedure Methods 0.000 claims description 9
- 241001465754 Metazoa Species 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical group N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 7
- 206010002383 Angina Pectoris Diseases 0.000 claims description 6
- 206010003658 Atrial Fibrillation Diseases 0.000 claims description 6
- 208000020925 Bipolar disease Diseases 0.000 claims description 6
- 201000004311 Gilles de la Tourette syndrome Diseases 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 206010061921 Psychotic disorder due to a general medical condition Diseases 0.000 claims description 6
- 208000006011 Stroke Diseases 0.000 claims description 6
- 208000011963 Substance-induced psychotic disease Diseases 0.000 claims description 6
- 231100000393 Substance-induced psychotic disorder Toxicity 0.000 claims description 6
- 208000000323 Tourette Syndrome Diseases 0.000 claims description 6
- 208000016620 Tourette disease Diseases 0.000 claims description 6
- 208000032109 Transient ischaemic attack Diseases 0.000 claims description 6
- 208000006673 asthma Diseases 0.000 claims description 6
- 230000003542 behavioural effect Effects 0.000 claims description 6
- 239000003153 chemical reaction reagent Substances 0.000 claims description 6
- 238000003776 cleavage reaction Methods 0.000 claims description 6
- 230000035602 clotting Effects 0.000 claims description 6
- 208000029078 coronary artery disease Diseases 0.000 claims description 6
- 206010012601 diabetes mellitus Diseases 0.000 claims description 6
- 201000002545 drug psychosis Diseases 0.000 claims description 6
- 230000002964 excitative effect Effects 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 208000010125 myocardial infarction Diseases 0.000 claims description 6
- 206010036807 progressive multifocal leukoencephalopathy Diseases 0.000 claims description 6
- 230000007017 scission Effects 0.000 claims description 6
- 208000019116 sleep disease Diseases 0.000 claims description 6
- 201000010875 transient cerebral ischemia Diseases 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- 150000003891 oxalate salts Chemical group 0.000 claims description 5
- -1 tri-substituted phosphine Chemical class 0.000 claims description 5
- 125000004650 C1-C8 alkynyl group Chemical group 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 239000013078 crystal Substances 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 4
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 4
- 238000001179 sorption measurement Methods 0.000 claims description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 4
- 230000003301 hydrolyzing effect Effects 0.000 claims description 3
- UFXKNUCUAXZUEB-UHFFFAOYSA-N 5-chloro-1-methylpyrazole Chemical compound CN1N=CC=C1Cl UFXKNUCUAXZUEB-UHFFFAOYSA-N 0.000 claims description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 239000012649 demethylating agent Substances 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 claims description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-O morpholinium Chemical compound [H+].C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-O 0.000 claims description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-M oxalate(1-) Chemical compound OC(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-M 0.000 claims description 2
- 235000006408 oxalic acid Nutrition 0.000 claims description 2
- 125000004497 pyrazol-5-yl group Chemical group N1N=CC=C1* 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims 2
- 0 CCC*1CC*CC1 Chemical compound CCC*1CC*CC1 0.000 description 4
- ZTYLFNWFXGDYOB-UHFFFAOYSA-N CC1[IH]C1c(cc(cc1-c2ccn[n]2C)N)c1O Chemical compound CC1[IH]C1c(cc(cc1-c2ccn[n]2C)N)c1O ZTYLFNWFXGDYOB-UHFFFAOYSA-N 0.000 description 2
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US80178906P | 2006-05-18 | 2006-05-18 | |
| US60/801,789 | 2006-05-18 | ||
| US92131807P | 2007-04-02 | 2007-04-02 | |
| 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 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009537544A JP2009537544A (ja) | 2009-10-29 |
| JP2009537544A5 true JP2009537544A5 (cg-RX-API-DMAC7.html) | 2011-06-30 |
| JP5286254B2 JP5286254B2 (ja) | 2013-09-11 |
Family
ID=38590318
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009511063A Expired - Fee Related JP5286254B2 (ja) | 2006-05-18 | 2007-05-17 | ５−ｈｔ２ａセロトニンレセプター活性のモジュレーターとして有用なフェニルピラゾールの結晶形態および調製方法 |
Country Status (16)
| Country | Link |
|---|---|
| US (4) | US8481535B2 (cg-RX-API-DMAC7.html) |
| EP (2) | EP2018372B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP5286254B2 (cg-RX-API-DMAC7.html) |
| KR (1) | KR101514846B1 (cg-RX-API-DMAC7.html) |
| CN (1) | CN102827081A (cg-RX-API-DMAC7.html) |
| AU (1) | AU2007254255B2 (cg-RX-API-DMAC7.html) |
| BR (1) | BRPI0712030A2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2646081C (cg-RX-API-DMAC7.html) |
| EA (1) | EA016675B1 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2543718T3 (cg-RX-API-DMAC7.html) |
| IL (2) | IL193822A (cg-RX-API-DMAC7.html) |
| MX (2) | MX2008014622A (cg-RX-API-DMAC7.html) |
| MY (1) | MY154962A (cg-RX-API-DMAC7.html) |
| NZ (2) | NZ594353A (cg-RX-API-DMAC7.html) |
| SG (1) | SG171681A1 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2007136689A2 (cg-RX-API-DMAC7.html) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1558582B1 (en) | 2003-07-22 | 2005-12-21 | 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 |
| PE20061130A1 (es) | 2004-11-19 | 2007-01-05 | Arena Pharm Inc | Derivados de 3-fenil-pirazol como moduladores del receptor de serotonina 5-ht2a |
| WO2007136689A2 (en) | 2006-05-18 | 2007-11-29 | Arena Pharmaceuticals, Inc. | Crystalline forms and processes for the preparation of phenyl-pyrazoles useful as modulators of the 5-ht2a serotonin receptor |
| EP2018371B1 (en) | 2006-05-18 | 2015-03-04 | Arena Pharmaceuticals, Inc. | Primary amines and derivatives thereof as modulators of the 5-ht2a serotonin receptor useful for the treatment of disorders related thereto |
| CN104761498B (zh) | 2006-05-18 | 2017-12-26 | 艾尼纳制药公司 | 5‑ht2a血清素受体的调节剂 |
| 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 |
| US9567327B2 (en) | 2007-08-15 | 2017-02-14 | Arena Pharmaceuticals, Inc. | Imidazo[1,2-a]pyridine derivatives as modulators of the 5-HT2A serotonin receptor useful for the treatment of disorders related thereto |
| 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 |
| US9126946B2 (en) | 2008-10-28 | 2015-09-08 | 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 |
| NO2364142T3 (cg-RX-API-DMAC7.html) | 2008-10-28 | 2018-06-16 | ||
| US8980891B2 (en) | 2009-12-18 | 2015-03-17 | 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 |
| WO2011139765A2 (en) * | 2010-04-27 | 2011-11-10 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| CN109562085A (zh) | 2015-06-12 | 2019-04-02 | 阿速万科学有限责任公司 | 用于预防和治疗rem睡眠行为障碍的二芳基和芳基杂芳基脲衍生物 |
| KR20180064373A (ko) | 2015-07-15 | 2018-06-14 | 엑소반트 사이언시즈 게엠베하 | 신경퇴행성 질환과 관련된 환각의 예방 및 치료에 유용한 5-ht2a 세로토닌 수용체의 조절자로서의 다이아릴 및 아릴헤테로아릴 우레아 유도체 |
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| DE2928485A1 (de) | 1979-07-14 | 1981-01-29 | Bayer Ag | Verwendung von harnstoffderivaten als arzneimittel bei der behandlung von fettstoffwechselstoerungen |
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-
2007
- 2007-05-17 WO PCT/US2007/011810 patent/WO2007136689A2/en not_active Ceased
- 2007-05-17 JP JP2009511063A patent/JP5286254B2/ja not_active Expired - Fee Related
- 2007-05-17 MY MYPI20084456A patent/MY154962A/en unknown
- 2007-05-17 MX MX2008014622A patent/MX2008014622A/es active IP Right Grant
- 2007-05-17 US US12/301,212 patent/US8481535B2/en active Active
- 2007-05-17 AU AU2007254255A patent/AU2007254255B2/en not_active Ceased
- 2007-05-17 KR KR1020087028020A patent/KR101514846B1/ko not_active Expired - Fee Related
- 2007-05-17 EP EP20070794969 patent/EP2018372B1/en active Active
- 2007-05-17 CN CN2012102989512A patent/CN102827081A/zh active Pending
- 2007-05-17 EA EA200870544A patent/EA016675B1/ru not_active IP Right Cessation
- 2007-05-17 NZ NZ594353A patent/NZ594353A/xx not_active IP Right Cessation
- 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 CA CA2646081A patent/CA2646081C/en not_active Expired - Fee Related
- 2007-05-17 EP EP12162245A patent/EP2527329A1/en not_active Withdrawn
- 2007-05-17 ES ES07794969.1T patent/ES2543718T3/es active Active
- 2007-05-17 NZ NZ571829A patent/NZ571829A/en not_active IP Right Cessation
- 2007-05-17 MX MX2013007579A patent/MX349156B/es unknown
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2008
- 2008-09-01 IL IL193822A patent/IL193822A/en active IP Right Grant
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- 2012-10-10 IL IL222340A patent/IL222340A/en active IP Right Grant
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2013
- 2013-07-03 US US13/935,329 patent/US9199940B2/en active Active
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- 2015-10-23 US US14/921,651 patent/US9783502B2/en active Active
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- 2017-09-11 US US15/700,670 patent/US20180186748A1/en not_active Abandoned
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