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 (enExample) | 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 (enExample) |
| EP (2) | EP2328414B1 (enExample) |
| JP (3) | JP5183808B2 (enExample) |
| KR (1) | KR20110063479A (enExample) |
| CN (2) | CN102176826B (enExample) |
| AU (1) | AU2009285533B2 (enExample) |
| BR (1) | BRPI0912928A2 (enExample) |
| CA (1) | CA2735549A1 (enExample) |
| DK (1) | DK2328414T3 (enExample) |
| EA (1) | EA020071B1 (enExample) |
| ES (1) | ES2451542T3 (enExample) |
| HR (1) | HRP20140195T1 (enExample) |
| MX (1) | MX2011002278A (enExample) |
| PL (1) | PL2328414T3 (enExample) |
| PT (1) | PT2328414E (enExample) |
| WO (1) | WO2010025407A1 (enExample) |
| ZA (1) | ZA201102123B (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2328414B1 (en) | 2008-08-29 | 2013-12-11 | Concert Pharmaceuticals Inc. | Substituted triazolo-pyridazine derivatives |
| US20110177468A1 (en) | 2008-10-03 | 2011-07-21 | Fabiola Barbosa Ormiga Galvao | Method and device for removing metallic fragments and metallic elements from dental root canals |
| EP2454259A1 (en) | 2009-06-23 | 2012-05-23 | Concert Pharmaceuticals Inc. | Deuterium-modified triazolo-pyridazine derivatives as gaba-a receptor modulators |
| EP2768509B1 (en) | 2011-10-20 | 2017-03-22 | Glaxosmithkline LLC | Substituted bicyclic aza-heterocycles and analogues as sirtuin modulators |
| WO2013059589A1 (en) * | 2011-10-20 | 2013-04-25 | Sirtris Pharmaceuticals, Inc. | Substituted bicyclic aza-heterocycles and analogues as sirtuin modulators |
| 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 |
| US20150119398A1 (en) | 2012-05-11 | 2015-04-30 | 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 |
| WO2013170241A1 (en) | 2012-05-11 | 2013-11-14 | 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]triazolol[4,3b]pyridazine |
| 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 |
| 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 |
| WO2015120110A2 (en) | 2014-02-07 | 2015-08-13 | Auspex Pharmaceuticals, Inc. | Novel pharmaceutical formulations |
| CN104353078B (zh) * | 2014-11-24 | 2017-10-24 | 王寿世 | 一种麻醉用药物组合物 |
| 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 |
| US10026332B1 (en) | 2017-04-10 | 2018-07-17 | Jasmine Gupta | Method to deliver contextual educational information utilizing smart wearables |
| US20220152037A1 (en) * | 2019-03-18 | 2022-05-19 | Neurocycle Therapeutic, Inc. | Use of gabaa receptor modulators for treatment of pain |
| CA3248309A1 (en) * | 2022-04-20 | 2023-10-26 | Engrail Therapeutics, Inc. | γ-AMINOBUTYRIC ACID 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 |
| ES2293638T3 (es) | 1994-03-25 | 2008-03-16 | Isotechnika, Inc. | Mejora de la eficacia de farmacos por deuteracion. |
| US6221335B1 (en) * | 1994-03-25 | 2001-04-24 | Isotechnika, Inc. | Method of using deuterated calcium channel blockers |
| ATE236904T1 (de) * | 1996-07-25 | 2003-04-15 | Merck Sharp & Dohme | Substituierte triazolo-pyridazin-derivate als liganden von gaba-rezeptoren |
| US6579875B1 (en) * | 1998-01-21 | 2003-06-17 | Merck Sharp & Dohme Limited | 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 |
| DE60016566T2 (de) * | 1999-01-27 | 2005-12-15 | Merck Sharp & Dohme Ltd., Hoddesdon | Triazolopyridazinderivate als liganden für gaba-rezeptoren |
| EP1104760B1 (en) * | 1999-12-03 | 2003-03-12 | Pfizer Products Inc. | Sulfamoylheteroaryl pyrazole compounds as anti-inflammatory/analgesic agents |
| 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 |
| ATE371193T1 (de) * | 2002-11-28 | 2007-09-15 | Neurosearch As | Verfahren zum screening für verbindungen mit sedativer oder anxiolytischer potenz |
| 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 |
| CA2624179A1 (en) * | 2005-10-06 | 2007-04-12 | 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 |
| EP2054063A4 (en) * | 2006-08-22 | 2010-10-27 | Concert Pharmaceuticals Inc | 4-AMINOCHINAZOLINE DERIVATIVES AND METHOD FOR THEIR USE |
| WO2008030382A1 (en) * | 2006-09-05 | 2008-03-13 | Schering Corporation | Pharmaceutical combinations for lipid management and in the treatment of atherosclerosis and hepatic steatosis |
| US20080242687A1 (en) * | 2007-04-02 | 2008-10-02 | Auspex Pharmaceuticals, Inc. | Substituted pyrimidines |
| EP2328414B1 (en) * | 2008-08-29 | 2013-12-11 | Concert Pharmaceuticals Inc. | Substituted triazolo-pyridazine derivatives |
-
2009
- 2009-08-28 EP EP20090810685 patent/EP2328414B1/en active Active
- 2009-08-28 JP JP2011525250A patent/JP5183808B2/ja not_active Expired - Fee Related
- 2009-08-28 CN CN200980140350.5A patent/CN102176826B/zh not_active Expired - Fee Related
- 2009-08-28 CA CA 2735549 patent/CA2735549A1/en not_active Abandoned
- 2009-08-28 HR HRP20140195AT patent/HRP20140195T1/hr unknown
- 2009-08-28 PL PL09810685T patent/PL2328414T3/pl unknown
- 2009-08-28 PT PT98106859T patent/PT2328414E/pt unknown
- 2009-08-28 EA EA201100409A patent/EA020071B1/ru not_active IP Right Cessation
- 2009-08-28 ES ES09810685T patent/ES2451542T3/es active Active
- 2009-08-28 AU AU2009285533A patent/AU2009285533B2/en not_active Ceased
- 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 DK DK09810685.9T patent/DK2328414T3/en active
- 2009-08-28 US US12/550,346 patent/US8003646B2/en active Active
- 2009-08-28 EP EP20130196185 patent/EP2716158A1/en not_active Withdrawn
- 2009-08-28 CN CN201410346402.7A patent/CN104098578A/zh active Pending
- 2009-08-28 MX MX2011002278A patent/MX2011002278A/es active IP Right Grant
- 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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