JP5972367B2 - 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 - Google Patents
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 Download PDFInfo
- Publication number
- JP5972367B2 JP5972367B2 JP2014517749A JP2014517749A JP5972367B2 JP 5972367 B2 JP5972367 B2 JP 5972367B2 JP 2014517749 A JP2014517749 A JP 2014517749A JP 2014517749 A JP2014517749 A JP 2014517749A JP 5972367 B2 JP5972367 B2 JP 5972367B2
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- thiadiazol
- piperazine
- ethyl
- chloro
- 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.)
- Expired - Fee Related
Links
- 0 *N(CC1)CCN1c1nc(I*N)n[s]1 Chemical compound *N(CC1)CCN1c1nc(I*N)n[s]1 0.000 description 1
- WNSSMBQLKHGDIY-UHFFFAOYSA-N C=C(S/N=C(\N)/I)Cl Chemical compound C=C(S/N=C(\N)/I)Cl WNSSMBQLKHGDIY-UHFFFAOYSA-N 0.000 description 1
- XYOAMMWCXYDWLM-UHFFFAOYSA-N COc1cc(CCN(CC2)CCN2c2nc(-c(cc3)ccc3Cl)n[s]2)ccn1 Chemical compound COc1cc(CCN(CC2)CCN2c2nc(-c(cc3)ccc3Cl)n[s]2)ccn1 XYOAMMWCXYDWLM-UHFFFAOYSA-N 0.000 description 1
- PWBSJUJINZLOQZ-UHFFFAOYSA-N COc1cc(CCN(CC2)CCN2c2nc(-c3cc(Cl)ccc3)n[s]2)ccc1 Chemical compound COc1cc(CCN(CC2)CCN2c2nc(-c3cc(Cl)ccc3)n[s]2)ccc1 PWBSJUJINZLOQZ-UHFFFAOYSA-N 0.000 description 1
- ZYKSCGMOAHKGGS-UHFFFAOYSA-N COc1cc(CCN(CC2)CCN2c2nc(-c3cccc(OC)c3)n[s]2)ccc1 Chemical compound COc1cc(CCN(CC2)CCN2c2nc(-c3cccc(OC)c3)n[s]2)ccc1 ZYKSCGMOAHKGGS-UHFFFAOYSA-N 0.000 description 1
- JUJZOWUQNMRVPO-UHFFFAOYSA-N COc1cc(CCN(CC2)CCN2c2nc(-c3ccncc3)n[s]2)ccc1 Chemical compound COc1cc(CCN(CC2)CCN2c2nc(-c3ccncc3)n[s]2)ccc1 JUJZOWUQNMRVPO-UHFFFAOYSA-N 0.000 description 1
- HJTXVAVBBIWREO-UHFFFAOYSA-N COc1ccc(CCCN(CC2)CCN2c2nc(-c(cc3)ccc3Cl)n[s]2)cc1 Chemical compound COc1ccc(CCCN(CC2)CCN2c2nc(-c(cc3)ccc3Cl)n[s]2)cc1 HJTXVAVBBIWREO-UHFFFAOYSA-N 0.000 description 1
- GBMADOGXCFEIIV-UHFFFAOYSA-N COc1ccc(CCN(CC2)CCN2c2nc(-c(cccc3)c3Cl)n[s]2)cc1 Chemical compound COc1ccc(CCN(CC2)CCN2c2nc(-c(cccc3)c3Cl)n[s]2)cc1 GBMADOGXCFEIIV-UHFFFAOYSA-N 0.000 description 1
- MEHZXXGPHPVZOI-UHFFFAOYSA-N COc1ccc(CCN(CC2)CCN2c2nc(-c3cc(C#N)ccc3)n[s]2)cc1 Chemical compound COc1ccc(CCN(CC2)CCN2c2nc(-c3cc(C#N)ccc3)n[s]2)cc1 MEHZXXGPHPVZOI-UHFFFAOYSA-N 0.000 description 1
- JKINLTJKGHLRNQ-UHFFFAOYSA-N COc1ccc(CCN(CC2)CCN2c2nc(-c3ccncc3)n[s]2)cc1 Chemical compound COc1ccc(CCN(CC2)CCN2c2nc(-c3ccncc3)n[s]2)cc1 JKINLTJKGHLRNQ-UHFFFAOYSA-N 0.000 description 1
- GTDIKKYDJJCBOU-UHFFFAOYSA-N COc1cccc(CCN(CC2)CCN2c2nc(-c3cc(Cl)cc(Cl)c3)n[s]2)c1 Chemical compound COc1cccc(CCN(CC2)CCN2c2nc(-c3cc(Cl)cc(Cl)c3)n[s]2)c1 GTDIKKYDJJCBOU-UHFFFAOYSA-N 0.000 description 1
- WROXPPZUVFYEEK-UHFFFAOYSA-N COc1nccc(CCN(CC2)CCN2c2nc(-c(cc3)ccc3C#N)n[s]2)c1 Chemical compound COc1nccc(CCN(CC2)CCN2c2nc(-c(cc3)ccc3C#N)n[s]2)c1 WROXPPZUVFYEEK-UHFFFAOYSA-N 0.000 description 1
- CWDIRRHPNNIIPG-UHFFFAOYSA-N COc1nccc(CCN(CC2)CCN2c2nc(-c3cc(Cl)ccc3)n[s]2)c1 Chemical compound COc1nccc(CCN(CC2)CCN2c2nc(-c3cc(Cl)ccc3)n[s]2)c1 CWDIRRHPNNIIPG-UHFFFAOYSA-N 0.000 description 1
- WTGLPFLGFOXSHD-UHFFFAOYSA-N Cc1c(CN(CC2)CCN2c2nc(-c(cc3)ncc3Cl)n[s]2)cccc1 Chemical compound Cc1c(CN(CC2)CCN2c2nc(-c(cc3)ncc3Cl)n[s]2)cccc1 WTGLPFLGFOXSHD-UHFFFAOYSA-N 0.000 description 1
- VFTHPJWTZAPDRL-UHFFFAOYSA-N FC(c1cc(CCN(CC2)CCN2c2nc(-c(cc3)ccc3Cl)n[s]2)ccc1)(F)F Chemical compound FC(c1cc(CCN(CC2)CCN2c2nc(-c(cc3)ccc3Cl)n[s]2)ccc1)(F)F VFTHPJWTZAPDRL-UHFFFAOYSA-N 0.000 description 1
- AZMBIGKRFHDKPD-UHFFFAOYSA-N FC(c1cc(CCN(CC2)CCN2c2nc(-c3cc(F)ccc3)n[s]2)ccc1)(F)F Chemical compound FC(c1cc(CCN(CC2)CCN2c2nc(-c3cc(F)ccc3)n[s]2)ccc1)(F)F AZMBIGKRFHDKPD-UHFFFAOYSA-N 0.000 description 1
- JMFQJCFTOUKUFW-UHFFFAOYSA-N Fc1ccc(CCN(CC2)CCN2c2nc(-c3cncc(Cl)c3)n[s]2)cc1 Chemical compound Fc1ccc(CCN(CC2)CCN2c2nc(-c3cncc(Cl)c3)n[s]2)cc1 JMFQJCFTOUKUFW-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/135—Nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
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 JP2014518240A5 (https=) | 2015-05-28 |
| JP5972367B2 true JP5972367B2 (ja) | 2016-08-17 |
Family
ID=46545347
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014517749A Expired - Fee Related 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 (https=) |
| EP (1) | EP2726470B1 (https=) |
| JP (1) | JP5972367B2 (https=) |
| CN (1) | CN103619825B (https=) |
| AU (1) | AU2012280420B2 (https=) |
| CA (1) | CA2837247C (https=) |
| ES (1) | ES2540956T3 (https=) |
| PL (1) | PL2726470T3 (https=) |
| WO (1) | WO2013004642A1 (https=) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9187440B2 (en) * | 2011-08-17 | 2015-11-17 | Remynd Nv | Piperazine thiazole derivatives useful in the treatment of tauopathies such as alzheimer's disease |
| WO2015140130A1 (en) * | 2014-03-17 | 2015-09-24 | Remynd Nv | Oxadiazole compounds |
| SG11201811023UA (en) | 2016-06-23 | 2019-01-30 | St Jude Childrens Res Hospital | Small molecule modulators of pantothenate kinases |
| JP2019533022A (ja) * | 2016-10-24 | 2019-11-14 | ユマニティ セラピューティクス,インコーポレーテッド | 化合物及びその使用 |
| EP3566055B1 (en) | 2017-01-06 | 2025-03-12 | Janssen Pharmaceutica NV | Scd inhibitor for the treatment of neurological disorders |
| CA3083000A1 (en) | 2017-10-24 | 2019-05-02 | Yumanity Therapeutics, Inc. | Compounds and uses thereof |
| WO2019133635A1 (en) | 2017-12-27 | 2019-07-04 | St. Jude Children's Research Hospital | Small molecule modulators of pantothenate kinases |
| JP7527967B2 (ja) | 2017-12-27 | 2024-08-05 | セント ジュード チルドレンズ リサーチ ホスピタル,インコーポレイティド | Castorに関連する障害を治療する方法 |
| WO2019183587A1 (en) | 2018-03-23 | 2019-09-26 | Yumanity Therapeutics, Inc. | Compounds and uses thereof |
| WO2020154571A1 (en) | 2019-01-24 | 2020-07-30 | Yumanity Therapeutics, Inc. | Compounds and uses thereof |
| 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 |
|---|---|---|---|---|
| CA2361179A1 (en) * | 1999-03-03 | 2000-09-08 | American Home Products Corporation | New diazole derivatives as serotonergic agents |
| DE60003911T2 (de) * | 1999-04-26 | 2004-05-27 | Neurosearch A/S | Heteroaryl-diazacycloalkane, ihre herstellung und verwendung |
| DE102004032567A1 (de) * | 2004-07-05 | 2006-03-02 | Grünenthal GmbH | Substituierte 1-Propiolyl-piperazine |
| US7541359B2 (en) * | 2005-06-30 | 2009-06-02 | Janssen Pharmaceutica N.V. | N-heteroarylpiperazinyl ureas as modulators of fatty acid amide hydrolase |
| WO2007092435A2 (en) * | 2006-02-07 | 2007-08-16 | Wyeth | 11-beta hsd1 inhibitors |
| GB0602335D0 (en) * | 2006-02-07 | 2006-03-15 | Remynd Nv | Thiadiazole Derivatives For The Treatment Of Neurodegenerative Diseases |
-
2012
- 2012-06-29 AU AU2012280420A patent/AU2012280420B2/en not_active Ceased
- 2012-06-29 ES ES12737238.1T patent/ES2540956T3/es active Active
- 2012-06-29 CA CA2837247A patent/CA2837247C/en 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 JP JP2014517749A patent/JP5972367B2/ja not_active Expired - Fee Related
- 2012-06-29 CN CN201280030881.0A patent/CN103619825B/zh active Active
- 2012-06-29 EP EP20120737238 patent/EP2726470B1/en active Active
- 2012-06-29 US US14/127,779 patent/US9023852B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| EP2726470A1 (en) | 2014-05-07 |
| WO2013004642A1 (en) | 2013-01-10 |
| ES2540956T3 (es) | 2015-07-15 |
| CN103619825B (zh) | 2015-10-14 |
| AU2012280420A1 (en) | 2013-12-12 |
| JP2014518240A (ja) | 2014-07-28 |
| CA2837247C (en) | 2020-03-31 |
| AU2012280420B2 (en) | 2017-01-05 |
| US9023852B2 (en) | 2015-05-05 |
| CN103619825A (zh) | 2014-03-05 |
| CA2837247A1 (en) | 2013-01-10 |
| US20140128404A1 (en) | 2014-05-08 |
| EP2726470B1 (en) | 2015-04-29 |
| PL2726470T3 (pl) | 2015-09-30 |
| HK1192726A1 (en) | 2014-08-29 |
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