JP2014518240A5 - - Google Patents
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- Publication number
- JP2014518240A5 JP2014518240A5 JP2014517749A JP2014517749A JP2014518240A5 JP 2014518240 A5 JP2014518240 A5 JP 2014518240A5 JP 2014517749 A JP2014517749 A JP 2014517749A JP 2014517749 A JP2014517749 A JP 2014517749A JP 2014518240 A5 JP2014518240 A5 JP 2014518240A5
- Authority
- JP
- Japan
- Prior art keywords
- structural formula
- compound
- thiadiazole
- piperazine
- derivative
- 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 6
- 238000000034 method Methods 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000004867 thiadiazoles Chemical class 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WZXLJQFOOKUNSK-UHFFFAOYSA-N 5-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-3-(4-methylphenyl)-1,2,4-thiadiazole Chemical compound C1=CC(C)=CC=C1C1=NSC(N2CCN(CC=3C=C4OCOC4=CC=3)CC2)=N1 WZXLJQFOOKUNSK-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- BJMPGMOWXAYATG-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]piperazine;dihydrochloride Chemical compound Cl.Cl.C1=CC(F)=CC=C1CCN1CCNCC1 BJMPGMOWXAYATG-UHFFFAOYSA-N 0.000 description 1
- ZQXCQTAELHSNAT-UHFFFAOYSA-N 1-chloro-3-nitro-5-(trifluoromethyl)benzene Chemical group [O-][N+](=O)C1=CC(Cl)=CC(C(F)(F)F)=C1 ZQXCQTAELHSNAT-UHFFFAOYSA-N 0.000 description 1
- CEUHPOVLEQUFCC-UHFFFAOYSA-N 3,5-dichloro-1,2,4-thiadiazole Chemical compound ClC1=NSC(Cl)=N1 CEUHPOVLEQUFCC-UHFFFAOYSA-N 0.000 description 1
- ZCSNLYSNHLTVIG-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-[4-[2-(4-fluorophenyl)ethyl]piperazin-1-yl]-1,2,4-thiadiazole Chemical compound C1=CC(F)=CC=C1CCN1CCN(C=2SN=C(N=2)C=2C=C(Cl)C=CC=2)CC1 ZCSNLYSNHLTVIG-UHFFFAOYSA-N 0.000 description 1
- CXUWGEWQRCXJDC-UHFFFAOYSA-N 3-bromo-5-chloro-1,2,4-thiadiazole Chemical compound ClC1=NC(Br)=NS1 CXUWGEWQRCXJDC-UHFFFAOYSA-N 0.000 description 1
- MCYDZBILUHBASQ-UHFFFAOYSA-N 5-chloro-3-(3-fluorophenyl)-1,2,4-thiadiazole Chemical compound FC1=CC=CC(C=2N=C(Cl)SN=2)=C1 MCYDZBILUHBASQ-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 239000012039 electrophile Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11172324.3 | 2011-07-01 | ||
| EP11172324 | 2011-07-01 | ||
| PCT/EP2012/062778 WO2013004642A1 (en) | 2011-07-01 | 2012-06-29 | 1, 2, 4 -thiadiazol- 5 -ylpiperazine derivatives useful in the treatment neurodegenerative diseases |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014518240A JP2014518240A (ja) | 2014-07-28 |
| JP2014518240A5 true JP2014518240A5 (OSRAM) | 2015-05-28 |
| JP5972367B2 JP5972367B2 (ja) | 2016-08-17 |
Family
ID=46545347
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014517749A Active JP5972367B2 (ja) | 2011-07-01 | 2012-06-29 | 神経変性疾患の治療に有用な１，２，４−チアジアゾール−５−イルピペラジン誘導体 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US9023852B2 (OSRAM) |
| EP (1) | EP2726470B1 (OSRAM) |
| JP (1) | JP5972367B2 (OSRAM) |
| CN (1) | CN103619825B (OSRAM) |
| AU (1) | AU2012280420B2 (OSRAM) |
| CA (1) | CA2837247C (OSRAM) |
| ES (1) | ES2540956T3 (OSRAM) |
| PL (1) | PL2726470T3 (OSRAM) |
| WO (1) | WO2013004642A1 (OSRAM) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103649062B (zh) | 2011-08-17 | 2015-10-07 | 瑞敏德股份有限公司 | 用于治疗tau病变如阿尔茨海默病的哌嗪噻唑衍生物 |
| WO2015140130A1 (en) * | 2014-03-17 | 2015-09-24 | Remynd Nv | Oxadiazole compounds |
| EP3474667A4 (en) * | 2016-06-23 | 2019-11-27 | St. Jude Children's Research Hospital, Inc. | SMALL MOLECULAR MODULATORS OF PANTOTHENAT KINASES |
| US11970486B2 (en) | 2016-10-24 | 2024-04-30 | Janssen Pharmaceutica Nv | Compounds and uses thereof |
| JP2020514293A (ja) | 2017-01-06 | 2020-05-21 | ユマニティ セラピューティクス，インコーポレーテッド | 神経障害を治療する方法 |
| CA3083000A1 (en) | 2017-10-24 | 2019-05-02 | Yumanity Therapeutics, Inc. | Compounds and uses thereof |
| US11547709B2 (en) | 2017-12-27 | 2023-01-10 | St. Jude Children's Research Hospital, Inc. | Methods of treating disorders associated with castor |
| EP3731844A4 (en) | 2017-12-27 | 2021-08-18 | St. Jude Children's Research Hospital, Inc. | PANTOTHENATE KINASES SMALL MOLECULE MODULATORS |
| EP3768269B1 (en) | 2018-03-23 | 2025-08-20 | Janssen Pharmaceutica NV | Compounds and uses thereof |
| MX2021008903A (es) | 2019-01-24 | 2021-11-04 | Yumanity Therapeutics Inc | Compuestos y usos de los mismos. |
| EA202192047A1 (ru) | 2019-11-13 | 2021-12-08 | Юманити Терапьютикс, Инк. | Соединения и их применение |
| WO2025104092A1 (en) | 2023-11-13 | 2025-05-22 | Remynd N.V. | Modulators of septin 6 for use in the prevention and/or treatment of neurodegenerative disorders |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1161424B1 (en) * | 1999-03-03 | 2004-06-02 | Wyeth | New diazole derivatives as serotonergic agents |
| JP2002543070A (ja) * | 1999-04-26 | 2002-12-17 | ニューロサーチ、アクティーゼルスカブ | ヘテロアリールジアザシクロアルカン類、その製造方法及びその使用方法 |
| DE102004032567A1 (de) * | 2004-07-05 | 2006-03-02 | Grünenthal GmbH | Substituierte 1-Propiolyl-piperazine |
| WO2007005510A1 (en) * | 2005-06-30 | 2007-01-11 | Janssen Pharmaceutica N.V. | N-heteroarylpiperazinyl ureas as modulators of fatty acid amide hydrolase |
| RU2008132333A (ru) * | 2006-02-07 | 2010-03-20 | Вайет (Us) | Ингибиторы 11-бета hsd1 |
| GB0602335D0 (en) * | 2006-02-07 | 2006-03-15 | Remynd Nv | Thiadiazole Derivatives For The Treatment Of Neurodegenerative Diseases |
-
2012
- 2012-06-29 CN CN201280030881.0A patent/CN103619825B/zh active Active
- 2012-06-29 WO PCT/EP2012/062778 patent/WO2013004642A1/en not_active Ceased
- 2012-06-29 PL PL12737238T patent/PL2726470T3/pl unknown
- 2012-06-29 EP EP20120737238 patent/EP2726470B1/en active Active
- 2012-06-29 ES ES12737238.1T patent/ES2540956T3/es active Active
- 2012-06-29 JP JP2014517749A patent/JP5972367B2/ja active Active
- 2012-06-29 CA CA2837247A patent/CA2837247C/en active Active
- 2012-06-29 US US14/127,779 patent/US9023852B2/en active Active
- 2012-06-29 AU AU2012280420A patent/AU2012280420B2/en active Active
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