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) | CN104098578A (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 |
|---|---|---|---|---|
| HRP20140195T1 (hr) * | 2008-08-29 | 2014-04-11 | Concert Pharmaceuticals Inc. | Supstituirani derivati triazolopiridazina |
| 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 |
| KR20140077963A (ko) | 2011-10-20 | 2014-06-24 | 글락소스미스클라인 엘엘씨 | 시르투인 조절제로서의 치환된 비시클릭 아자-헤테로사이클 및 유사체 |
| 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 |
| BR112014016930A8 (pt) | 2012-01-11 | 2017-12-26 | Bayer Ip Gmbh | compostos tetrazol-5-il- e triazol-5-il-arila e uso destes como herbicidas |
| 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 |
| JP2015516440A (ja) * | 2012-05-11 | 2015-06-11 | 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 | ７−（ｔｅｒｔ−ブチル−ｄ９）−３−（２，５−ジフルオロフェニル）−６−（（１−メチル−１Ｈ−１，２，４−トリアゾール−５−イル）メトキシ）−［１，２，４］トリアゾロ［４，３−ｂ］ピリダジンの２型多形 |
| 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 |
| MX2016010213A (es) | 2014-02-07 | 2017-04-13 | Auspex Pharmaceuticals Inc | Formulaciones farmaceuticas novedosas. |
| 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 |
| WO2020191047A1 (en) * | 2019-03-18 | 2020-09-24 | Neurocycle Therapeutics, Inc. | Use of gabaa receptor modulators for treatment of pain |
| AU2023258030A1 (en) * | 2022-04-20 | 2024-10-17 | Engrail Therapeutics, Inc. | Gabaa receptor modulator salts, particles, and uses thereof |
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 |
| KR100477070B1 (ko) | 1994-03-25 | 2006-04-21 | 이소테크니카 인코포레이티드 | 중수소화작용에의한의약품의효능강화법 |
| EP0915875B1 (en) * | 1996-07-25 | 2003-04-09 | MERCK SHARP & DOHME LTD. | Substituted triazolo-pyridazine derivatives as ligands for gaba receptors |
| MXPA00007135A (es) * | 1998-01-21 | 2002-11-07 | Merck Sharp & Dohme | Derivados de triazolo-piridazina como ligandos para receptores gaba. |
| US6440710B1 (en) * | 1998-12-10 | 2002-08-27 | The Scripps Research Institute | Antibody-catalyzed deuteration, tritiation, dedeuteration or detritiation of carbonyl compounds |
| JP2002535407A (ja) * | 1999-01-27 | 2002-10-22 | メルク シャープ エンド ドーム リミテッド | Ｇａｂａ受容体のリガンドとしてのトリアゾロピリダジン誘導体 |
| DK1104760T3 (da) * | 1999-12-03 | 2003-06-30 | Pfizer Prod Inc | Sulfamoylheteroarylpyrazolforbindelser som anti-inflammatoriske/analgetiske midler |
| 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 |
| DE60315876T2 (de) * | 2002-11-28 | 2008-05-21 | Neurosearch A/S | 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 |
| CN101309917B (zh) * | 2005-10-06 | 2013-09-11 | 奥斯拜客斯制药有限公司 | 具有增强治疗性质的胃h+，k+-atp酶氘代抑制剂 |
| 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 |
| CA2661223A1 (en) * | 2006-08-22 | 2008-02-28 | Concert Pharmaceuticals Inc. | 4-aminoquinazoline derivatives and methods of use thereof |
| WO2008030382A1 (en) * | 2006-09-05 | 2008-03-13 | Schering Corporation | Pharmaceutical combinations for lipid management and in the treatment of atherosclerosis and hepatic steatosis |
| BRPI0809171A2 (pt) * | 2007-04-02 | 2014-09-16 | Auspex Pharmaceuticals Inc | "composto, composição farmacêutica, método para tratamento,prevençõ ou melhora de um ou mais , sintomas de uma desordem mediada pela endotelina em um sujeito, método de inibição de ligação d euma endotelina a um receptor eta ou etb e método para modular a atividade mediada pelo receptor de endotelina" |
| HRP20140195T1 (hr) * | 2008-08-29 | 2014-04-11 | Concert Pharmaceuticals Inc. | Supstituirani derivati triazolopiridazina |
-
2009
- 2009-08-28 HR HRP20140195AT patent/HRP20140195T1/hr unknown
- 2009-08-28 DK DK09810685.9T patent/DK2328414T3/en active
- 2009-08-28 BR BRPI0912928-6A patent/BRPI0912928A2/pt not_active IP Right Cessation
- 2009-08-28 AU AU2009285533A patent/AU2009285533B2/en not_active Ceased
- 2009-08-28 EP EP20090810685 patent/EP2328414B1/en active Active
- 2009-08-28 CA CA 2735549 patent/CA2735549A1/en not_active Abandoned
- 2009-08-28 ES ES09810685T patent/ES2451542T3/es active Active
- 2009-08-28 WO PCT/US2009/055427 patent/WO2010025407A1/en not_active Ceased
- 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 PL PL09810685T patent/PL2328414T3/pl unknown
- 2009-08-28 JP JP2011525250A patent/JP5183808B2/ja not_active Expired - Fee Related
- 2009-08-28 MX MX2011002278A patent/MX2011002278A/es active IP Right Grant
- 2009-08-28 CN CN201410346402.7A patent/CN104098578A/zh active Pending
- 2009-08-28 KR KR20117006632A patent/KR20110063479A/ko not_active Ceased
- 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 EA EA201100409A patent/EA020071B1/ru not_active IP Right Cessation
-
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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