JP2012501346A5 - - Google Patents
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- Publication number
- JP2012501346A5 JP2012501346A5 JP2011525250A JP2011525250A JP2012501346A5 JP 2012501346 A5 JP2012501346 A5 JP 2012501346A5 JP 2011525250 A JP2011525250 A JP 2011525250A JP 2011525250 A JP2011525250 A JP 2011525250A JP 2012501346 A5 JP2012501346 A5 JP 2012501346A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- pharmaceutically acceptable
- composition
- formula
- acceptable salt
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims 3
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 2
- 229910052805 deuterium Inorganic materials 0.000 claims 2
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 206010010904 Convulsion Diseases 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 230000036461 convulsion Effects 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000000155 isotopic effect Effects 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- QUAQZVSGXQVIEP-FIBGUPNXSA-N [2-(trideuteriomethyl)-1,2,4-triazol-3-yl]methanol Chemical compound [2H]C([2H])([2H])N1N=CN=C1CO QUAQZVSGXQVIEP-FIBGUPNXSA-N 0.000 description 5
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- BQDUNOMMYOKHEP-MGKWXGLJSA-N 3-(2,5-difluorophenyl)-7-[1,1,1,3,3,3-hexadeuterio-2-(trideuteriomethyl)propan-2-yl]-6-[[2-(trideuteriomethyl)-1,2,4-triazol-3-yl]methoxy]-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound [2H]C([2H])([2H])N1N=CN=C1COC(C(=C1)C(C([2H])([2H])[2H])(C([2H])([2H])[2H])C([2H])([2H])[2H])=NN2C1=NN=C2C1=CC(F)=CC=C1F BQDUNOMMYOKHEP-MGKWXGLJSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 210000004731 jugular vein Anatomy 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 2
- 238000013222 sprague-dawley male rat Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000005055 short column chromatography Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9329308P | 2008-08-29 | 2008-08-29 | |
| US61/093,293 | 2008-08-29 | ||
| PCT/US2009/055427 WO2010025407A1 (en) | 2008-08-29 | 2009-08-28 | Substituted triazolo-pyridazine derivatives |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013004449A Division JP5373982B2 (ja) | 2008-08-29 | 2013-01-15 | 置換トリアゾロ−ピリダジン誘導体 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012501346A JP2012501346A (ja) | 2012-01-19 |
| JP2012501346A5 true JP2012501346A5 (https=) | 2012-10-18 |
| JP5183808B2 JP5183808B2 (ja) | 2013-04-17 |
Family
ID=41721962
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011525250A Expired - Fee Related JP5183808B2 (ja) | 2008-08-29 | 2009-08-28 | 置換トリアゾロ−ピリダジン誘導体 |
| JP2013004449A Expired - Fee Related JP5373982B2 (ja) | 2008-08-29 | 2013-01-15 | 置換トリアゾロ−ピリダジン誘導体 |
| JP2013194060A Pending JP2014058518A (ja) | 2008-08-29 | 2013-09-19 | 置換トリアゾロ−ピリダジン誘導体 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013004449A Expired - Fee Related JP5373982B2 (ja) | 2008-08-29 | 2013-01-15 | 置換トリアゾロ−ピリダジン誘導体 |
| JP2013194060A Pending JP2014058518A (ja) | 2008-08-29 | 2013-09-19 | 置換トリアゾロ−ピリダジン誘導体 |
Country Status (17)
| Country | Link |
|---|---|
| US (4) | US8003646B2 (https=) |
| EP (2) | EP2328414B1 (https=) |
| JP (3) | JP5183808B2 (https=) |
| KR (1) | KR20110063479A (https=) |
| CN (2) | CN104098578A (https=) |
| AU (1) | AU2009285533B2 (https=) |
| BR (1) | BRPI0912928A2 (https=) |
| CA (1) | CA2735549A1 (https=) |
| DK (1) | DK2328414T3 (https=) |
| EA (1) | EA020071B1 (https=) |
| ES (1) | ES2451542T3 (https=) |
| HR (1) | HRP20140195T1 (https=) |
| MX (1) | MX2011002278A (https=) |
| PL (1) | PL2328414T3 (https=) |
| PT (1) | PT2328414E (https=) |
| WO (1) | WO2010025407A1 (https=) |
| ZA (1) | ZA201102123B (https=) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104098578A (zh) * | 2008-08-29 | 2014-10-15 | 康瑟特制药公司 | 取代的三唑并哒嗪衍生物 |
| WO2010037194A1 (pt) | 2008-10-03 | 2010-04-08 | Instituto Alberto Luiz De Coimbra De Pós Graduação E Pesquisa De Engenharia - Coppe/Ufrj | Dispositivo para remoção de fragmentos metálicos e elementos metálicos do interior de canáis radiculares de dentes e processo para remoção dos mesmos |
| JP2012531419A (ja) | 2009-06-23 | 2012-12-10 | コンサート ファーマシューティカルズ インコーポレイテッド | Ｇａｂａ−ａ受容体修飾物質としての重水素修飾されたトリアゾロピリダジン誘導体 |
| JP2014530870A (ja) * | 2011-10-20 | 2014-11-20 | グラクソスミスクライン・リミテッド・ライアビリティ・カンパニーＧｌａｘｏＳｍｉｔｈＫｌｉｎｅ ＬＬＣ | サーチュイン調節因子としての置換された二環式アザ複素環およびアナログ |
| JP6073343B2 (ja) | 2011-10-20 | 2017-02-01 | グラクソスミスクライン・リミテッド・ライアビリティ・カンパニーＧｌａｘｏＳｍｉｔｈＫｌｉｎｅ ＬＬＣ | サーチュイン調節因子としての置換された二環式アザ複素環およびアナログ |
| HK1201270A1 (en) | 2012-01-11 | 2015-08-28 | Bayer Intellectual Property Gmbh | Tetrazol-5-yl- and triazol-5-yl-aryl compounds and use thereof as herbicides |
| US20150099753A1 (en) * | 2012-05-11 | 2015-04-09 | Concert Pharmaceuticals Inc. | Form 5 polymorph of 7-(tert-butyl-d9)-3-(2,5-difluorophenyl)-6-((1-methyl-1h-1,2,4-triazol-5-yl)methoxy)-[1,2,4]triazolo[4,3-b]pyridazine |
| WO2013170242A1 (en) * | 2012-05-11 | 2013-11-14 | Concert Pharmaceuticals, Inc. | Form 2 polymorph of 7-(tert-butyl-d9)-3-(2,5-difluorophenyl)-6-((1-methyl-1h-1,2,4-triazol-5-yl)methoxy)-[1,2,4]triazolo[4,3-b]pyridazine |
| US20150158870A1 (en) * | 2012-05-11 | 2015-06-11 | Concert Pharmaceuticals Inc. | Polymorphs of 7-(tert-butyl-d9)-3-(2,5-difluorophenyl)-6-((1-methyl-1h-1,2,4-triazol-5-yl)methoxy)-[1,2,4]triazolo[4,3-b]pyridazine |
| WO2015052173A1 (en) | 2013-10-10 | 2015-04-16 | Basf Se | Tetrazole and triazole compounds and their use as herbicides |
| WO2015052178A1 (en) | 2013-10-10 | 2015-04-16 | Basf Se | 1,2,5-oxadiazole compounds and their use as herbicides |
| WO2015095549A1 (en) * | 2013-12-18 | 2015-06-25 | Concert Pharmaceuticals, Inc. | Dosage regimen for gabaa receptor subtype selective drug |
| KR20160117596A (ko) | 2014-02-07 | 2016-10-10 | 오스펙스 파마슈티칼스, 인코포레이티드 | 신규 제약 제제 |
| CN104474549A (zh) * | 2014-11-24 | 2015-04-01 | 王寿世 | 异丙酚和gabaa受体拮抗剂在制备麻醉药物中的用途 |
| CN104353078B (zh) * | 2014-11-24 | 2017-10-24 | 王寿世 | 一种麻醉用药物组合物 |
| US10026332B1 (en) | 2017-04-10 | 2018-07-17 | Jasmine Gupta | Method to deliver contextual educational information utilizing smart wearables |
| CA3132810A1 (en) * | 2019-03-18 | 2020-09-24 | Neurocycle Therapeutics, Inc. | Use of gabaa receptor modulators for treatment of fybromyalgia |
| EP4511025A4 (en) * | 2022-04-20 | 2026-04-15 | Engrail Therapeutics Inc | GABAa receptor modulator salts, particles, and their uses |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9321162D0 (en) | 1993-10-13 | 1993-12-01 | Boots Co Plc | Therapeutic agents |
| US6221335B1 (en) * | 1994-03-25 | 2001-04-24 | Isotechnika, Inc. | Method of using deuterated calcium channel blockers |
| ES2293638T3 (es) | 1994-03-25 | 2008-03-16 | Isotechnika, Inc. | Mejora de la eficacia de farmacos por deuteracion. |
| KR20000029548A (ko) * | 1996-07-25 | 2000-05-25 | 더블유. 지. 콜 | 가바수용체에대한리간드로서의치환된트리아졸로-피리다진유도체 |
| HUP0100575A3 (en) * | 1998-01-21 | 2003-03-28 | Merck Sharp & Dohme Ltd Hoddes | Triazolo-pyridazine derivatives as ligands for gaba receptors |
| US6440710B1 (en) * | 1998-12-10 | 2002-08-27 | The Scripps Research Institute | Antibody-catalyzed deuteration, tritiation, dedeuteration or detritiation of carbonyl compounds |
| ATE284403T1 (de) * | 1999-01-27 | 2004-12-15 | Merck Sharp & Dohme | Triazolopyridazinderivate als liganden für gaba- rezeptoren |
| PT1104760E (pt) * | 1999-12-03 | 2003-06-30 | Pfizer Prod Inc | Compostos de sulfamoil-heteroarilpirazole como agentes analgesicos e anti-inflamatorios |
| US20020165217A1 (en) * | 2001-05-01 | 2002-11-07 | Pfizer Inc. | Combination treatment for anxiety and depression |
| TW200413273A (en) * | 2002-11-15 | 2004-08-01 | Wako Pure Chem Ind Ltd | Heavy hydrogenation method of heterocyclic rings |
| WO2004048980A1 (en) * | 2002-11-28 | 2004-06-10 | Neurosearch A/S | Method for screening for compounds as potential sedatives or anxiolytics |
| WO2006061428A2 (en) | 2004-12-10 | 2006-06-15 | Universität Zürich | Gaba-a alpha 2 and alpha 3 receptor agonists for treating neuropathic, inflammatory and migraine associated pain |
| EP1934201A1 (en) * | 2005-10-06 | 2008-06-25 | Auspex Pharmaceuticals Inc. | Deuterated inhibitors of gastric h+, k+-atpase with enhanced therapeutic properties |
| US7750168B2 (en) * | 2006-02-10 | 2010-07-06 | Sigma-Aldrich Co. | Stabilized deuteroborane-tetrahydrofuran complex |
| JO2630B1 (en) | 2006-04-13 | 2012-06-17 | نوفارتيس ايه جي | Organic compounds |
| JP2010501572A (ja) * | 2006-08-22 | 2010-01-21 | コンサート ファーマシューティカルズ インコーポレイテッド | ４−アミノキナゾリン誘導体およびその使用方法 |
| US20080103122A1 (en) * | 2006-09-05 | 2008-05-01 | Schering Corporation | Pharmaceutical combinations for lipid management and in the treatment of atherosclerosis and hepatic steatosis |
| AU2008232425A1 (en) * | 2007-04-02 | 2008-10-09 | Auspex Pharmaceuticals, Inc. | Substituted pyrimidines |
| CN104098578A (zh) * | 2008-08-29 | 2014-10-15 | 康瑟特制药公司 | 取代的三唑并哒嗪衍生物 |
-
2009
- 2009-08-28 CN CN201410346402.7A patent/CN104098578A/zh active Pending
- 2009-08-28 EP EP20090810685 patent/EP2328414B1/en active Active
- 2009-08-28 HR HRP20140195AT patent/HRP20140195T1/hr unknown
- 2009-08-28 KR KR20117006632A patent/KR20110063479A/ko not_active Ceased
- 2009-08-28 BR BRPI0912928-6A patent/BRPI0912928A2/pt not_active IP Right Cessation
- 2009-08-28 MX MX2011002278A patent/MX2011002278A/es active IP Right Grant
- 2009-08-28 EA EA201100409A patent/EA020071B1/ru not_active IP Right Cessation
- 2009-08-28 EP EP20130196185 patent/EP2716158A1/en not_active Withdrawn
- 2009-08-28 JP JP2011525250A patent/JP5183808B2/ja not_active Expired - Fee Related
- 2009-08-28 ES ES09810685T patent/ES2451542T3/es active Active
- 2009-08-28 AU AU2009285533A patent/AU2009285533B2/en not_active Ceased
- 2009-08-28 PL PL09810685T patent/PL2328414T3/pl unknown
- 2009-08-28 DK DK09810685.9T patent/DK2328414T3/en active
- 2009-08-28 CA CA 2735549 patent/CA2735549A1/en not_active Abandoned
- 2009-08-28 PT PT98106859T patent/PT2328414E/pt unknown
- 2009-08-28 CN CN200980140350.5A patent/CN102176826B/zh not_active Expired - Fee Related
- 2009-08-28 US US12/550,346 patent/US8003646B2/en active Active
- 2009-08-28 WO PCT/US2009/055427 patent/WO2010025407A1/en not_active Ceased
-
2011
- 2011-03-22 ZA ZA2011/02123A patent/ZA201102123B/en unknown
- 2011-06-30 US US13/174,662 patent/US8399467B2/en active Active
-
2013
- 2013-01-15 JP JP2013004449A patent/JP5373982B2/ja not_active Expired - Fee Related
- 2013-03-18 US US13/846,119 patent/US8921366B2/en active Active
- 2013-09-19 JP JP2013194060A patent/JP2014058518A/ja active Pending
-
2014
- 2014-12-23 US US14/581,843 patent/US20150111895A1/en not_active Abandoned
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