JP2015524843A5 - - Google Patents
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- Publication number
- JP2015524843A5 JP2015524843A5 JP2015527538A JP2015527538A JP2015524843A5 JP 2015524843 A5 JP2015524843 A5 JP 2015524843A5 JP 2015527538 A JP2015527538 A JP 2015527538A JP 2015527538 A JP2015527538 A JP 2015527538A JP 2015524843 A5 JP2015524843 A5 JP 2015524843A5
- Authority
- JP
- Japan
- Prior art keywords
- compound according
- piperidin
- alkyl
- amine
- pharmaceutically acceptable
- 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
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- 150000001875 compounds Chemical class 0.000 claims 21
- 125000000217 alkyl group Chemical group 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 9
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 125000001475 halogen functional group Chemical group 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 4
- 150000001408 amides Chemical class 0.000 claims 4
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000004043 oxo group Chemical group O=* 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 3
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 2
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- FGSQKAOOHDQJBL-UHFFFAOYSA-N (4-chloro-2,6-difluorophenyl)-[1-[2-(cyclopropylamino)pyrido[3,4-b]pyrazin-3-yl]piperidin-4-yl]methanone Chemical compound FC1=CC(Cl)=CC(F)=C1C(=O)C1CCN(C=2C(=NC3=CC=NC=C3N=2)NC2CC2)CC1 FGSQKAOOHDQJBL-UHFFFAOYSA-N 0.000 claims 1
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- UDDLUEJQXZPSPI-UHFFFAOYSA-N 2-(cyclopropylamino)-3-[4-(2,4-difluorophenoxy)piperidin-1-yl]-n,n-dimethylpyrido[3,4-b]pyrazine-7-carboxamide Chemical compound C1CC(OC=2C(=CC(F)=CC=2)F)CCN1C=1N=C2C=NC(C(=O)N(C)C)=CC2=NC=1NC1CC1 UDDLUEJQXZPSPI-UHFFFAOYSA-N 0.000 claims 1
- RAOLSNVZAPAUKM-QFIPXVFZSA-N 2-(cyclopropylamino)-3-[4-[(s)-(2,4-difluorophenyl)-fluoromethyl]piperidin-1-yl]quinoxaline-6-carbonitrile Chemical compound C1CC([C@H](F)C=2C(=CC(F)=CC=2)F)CCN1C1=NC2=CC(C#N)=CC=C2N=C1NC1CC1 RAOLSNVZAPAUKM-QFIPXVFZSA-N 0.000 claims 1
- AUDOCEFSDPEPOQ-UHFFFAOYSA-N 2-[4-[(3-chlorophenyl)methyl]piperazin-1-yl]-n-phenylpyrido[2,3-b]pyrazin-3-amine Chemical compound ClC1=CC=CC(CN2CCN(CC2)C=2C(=NC3=NC=CC=C3N=2)NC=2C=CC=CC=2)=C1 AUDOCEFSDPEPOQ-UHFFFAOYSA-N 0.000 claims 1
- POQVINGNYFSKHL-UHFFFAOYSA-N 3-[4-(2,4-difluorophenoxy)piperidin-1-yl]-n-propan-2-ylpyrazino[2,3-d]pyridazin-2-amine Chemical compound CC(C)NC1=NC2=CN=NC=C2N=C1N(CC1)CCC1OC1=CC=C(F)C=C1F POQVINGNYFSKHL-UHFFFAOYSA-N 0.000 claims 1
- RYJKNTCXWUMJQE-UHFFFAOYSA-N 3-[4-(2-fluoro-4-methoxyphenoxy)piperidin-1-yl]-n-propan-2-ylpyrazino[2,3-d]pyridazin-2-amine Chemical compound FC1=CC(OC)=CC=C1OC1CCN(C=2C(=NC3=CN=NC=C3N=2)NC(C)C)CC1 RYJKNTCXWUMJQE-UHFFFAOYSA-N 0.000 claims 1
- CAUFFIPILPUPFY-UHFFFAOYSA-N 3-[4-(4-chloro-2-fluorophenoxy)piperidin-1-yl]-n,n-dimethyl-2-(propan-2-ylamino)pyrido[3,4-b]pyrazine-7-carboxamide Chemical compound CC(C)NC1=NC2=CC(C(=O)N(C)C)=NC=C2N=C1N(CC1)CCC1OC1=CC=C(Cl)C=C1F CAUFFIPILPUPFY-UHFFFAOYSA-N 0.000 claims 1
- RNXQWNOMRRLRKJ-UHFFFAOYSA-N 3-[4-[(4-bromophenyl)methyl]piperazin-1-yl]-n-cyclopropylquinoxalin-2-amine Chemical compound C1=CC(Br)=CC=C1CN1CCN(C=2C(=NC3=CC=CC=C3N=2)NC2CC2)CC1 RNXQWNOMRRLRKJ-UHFFFAOYSA-N 0.000 claims 1
- HLOASCLRFLCWBF-UHFFFAOYSA-N 3-[4-[2-chloro-5-(trifluoromethyl)phenyl]sulfonylpiperazin-1-yl]-2-(cyclopropylamino)quinoxaline-6-carbonitrile Chemical compound FC(F)(F)C1=CC=C(Cl)C(S(=O)(=O)N2CCN(CC2)C=2C(=NC3=CC=C(C=C3N=2)C#N)NC2CC2)=C1 HLOASCLRFLCWBF-UHFFFAOYSA-N 0.000 claims 1
- PWJURAYPJMGEQA-UHFFFAOYSA-N N-cyclopropyl-3-[4-[(2,4-difluorophenyl)methyl]piperidin-1-yl]-5-methylpyrido[3,4-b]pyrazin-2-amine Chemical compound Cc1nccc2nc(NC3CC3)c(nc12)N1CCC(Cc2ccc(F)cc2F)CC1 PWJURAYPJMGEQA-UHFFFAOYSA-N 0.000 claims 1
- FTLRJAGVMBRGOE-OAQYLSRUSA-N N-cyclopropyl-3-[4-[(R)-(2,4-difluorophenyl)-fluoromethyl]piperidin-1-yl]-7-methylpyrido[3,4-b]pyrazin-2-amine Chemical compound Cc1cc2nc(NC3CC3)c(nc2cn1)N1CCC(CC1)[C@@H](F)c1ccc(F)cc1F FTLRJAGVMBRGOE-OAQYLSRUSA-N 0.000 claims 1
- RNCMYJCSPNFZKH-UHFFFAOYSA-N [1-[2-(cyclopropylamino)pyrido[3,4-b]pyrazin-3-yl]piperidin-4-yl]-pyrrolidin-1-ylmethanone Chemical compound C1CCCN1C(=O)C(CC1)CCN1C1=NC2=CN=CC=C2N=C1NC1CC1 RNCMYJCSPNFZKH-UHFFFAOYSA-N 0.000 claims 1
- WUHOXGAMPICNGF-UHFFFAOYSA-N [4-[3-(cyclopropylamino)quinoxalin-2-yl]piperazin-1-yl]-(2,5-dichlorophenyl)methanone Chemical compound ClC1=CC=C(Cl)C(C(=O)N2CCN(CC2)C=2C(=NC3=CC=CC=C3N=2)NC2CC2)=C1 WUHOXGAMPICNGF-UHFFFAOYSA-N 0.000 claims 1
- UMGXEJAJNJNUDE-UHFFFAOYSA-N [4-[3-(cyclopropylamino)quinoxalin-2-yl]piperazin-1-yl]-(3-propan-2-ylphenyl)methanone Chemical compound CC(C)C1=CC=CC(C(=O)N2CCN(CC2)C=2C(=NC3=CC=CC=C3N=2)NC2CC2)=C1 UMGXEJAJNJNUDE-UHFFFAOYSA-N 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000004103 aminoalkyl group Chemical group 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000004476 heterocycloamino group Chemical group 0.000 claims 1
- LCJLAMYJOWBDDR-UHFFFAOYSA-N n-cyclobutyl-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]pyrido[3,4-b]pyrazin-3-amine Chemical compound FC1=CC(F)=CC=C1OC1CCN(C=2C(=NC3=CN=CC=C3N=2)NC2CCC2)CC1 LCJLAMYJOWBDDR-UHFFFAOYSA-N 0.000 claims 1
- WRBYOTSWEJDNOE-UHFFFAOYSA-N n-cyclopropyl-3-[4-[(3-methylphenyl)methyl]piperazin-1-yl]quinoxalin-2-amine Chemical compound CC1=CC=CC(CN2CCN(CC2)C=2C(=NC3=CC=CC=C3N=2)NC2CC2)=C1 WRBYOTSWEJDNOE-UHFFFAOYSA-N 0.000 claims 1
- HXYDVCIOEYYMFT-UHFFFAOYSA-N n-cyclopropyl-3-[4-[2-(2,5-dichlorophenyl)ethyl]piperazin-1-yl]quinoxalin-2-amine Chemical compound ClC1=CC=C(Cl)C(CCN2CCN(CC2)C=2C(=NC3=CC=CC=C3N=2)NC2CC2)=C1 HXYDVCIOEYYMFT-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000005309 thioalkoxy group Chemical group 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261682704P | 2012-08-13 | 2012-08-13 | |
| US61/682,704 | 2012-08-13 | ||
| US201261696748P | 2012-09-04 | 2012-09-04 | |
| US61/696,748 | 2012-09-04 | ||
| PCT/US2013/054715 WO2014028479A1 (en) | 2012-08-13 | 2013-08-13 | Quinoxaline derivatives as gpr6 modulators |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017154601A Division JP6389933B2 (ja) | 2012-08-13 | 2017-08-09 | Ｇｐｒ６モジュレーターとしてのキノキサリン誘導体 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015524843A JP2015524843A (ja) | 2015-08-27 |
| JP2015524843A5 true JP2015524843A5 (enExample) | 2016-09-29 |
| JP6193374B2 JP6193374B2 (ja) | 2017-09-06 |
Family
ID=48998764
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015527538A Active JP6193374B2 (ja) | 2012-08-13 | 2013-08-13 | Ｇｐｒ６モジュレーターとしてのキノキサリン誘導体 |
| JP2017154601A Active JP6389933B2 (ja) | 2012-08-13 | 2017-08-09 | Ｇｐｒ６モジュレーターとしてのキノキサリン誘導体 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017154601A Active JP6389933B2 (ja) | 2012-08-13 | 2017-08-09 | Ｇｐｒ６モジュレーターとしてのキノキサリン誘導体 |
Country Status (4)
| Country | Link |
|---|---|
| US (2) | US9487526B2 (enExample) |
| EP (1) | EP2882722B1 (enExample) |
| JP (2) | JP6193374B2 (enExample) |
| WO (1) | WO2014028479A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9487526B2 (en) * | 2012-08-13 | 2016-11-08 | Takeda Pharmaceutical Company Limited | Quinoxaline derivatives as GPR6 modulators |
| JO3466B1 (ar) * | 2013-12-20 | 2020-07-05 | Takeda Pharmaceuticals Co | مواد ضابطة لتترا هيدرو بيريدوبيرازينات من gpr6 |
| UA117779C2 (uk) * | 2014-02-14 | 2018-09-25 | Такеда Фармасьютікал Компані Лімітед | Піразини як модулятори gpr6 |
| JP6526034B2 (ja) * | 2014-02-14 | 2019-06-05 | 武田薬品工業株式会社 | Ｇｐｒ６のピリドピラジンモジュレーター |
| CN110520127B (zh) * | 2017-03-26 | 2023-05-16 | 武田药品工业株式会社 | 作为gpr6的调节剂的经哌啶基取代的杂芳族羧酰胺和经哌嗪基取代的杂芳族羧酰胺 |
| EP4568668A4 (en) * | 2022-08-11 | 2026-07-29 | Maplight Therapeutics Inc | GPR6 Inverse Agonists |
| CN115636797A (zh) * | 2022-10-19 | 2023-01-24 | 台州国赐医药技术有限公司 | 一种制备5,6-二氯-2,3-吡嗪二酸的方法 |
| WO2025160132A1 (en) * | 2024-01-23 | 2025-07-31 | Maplight Therapeutics, Inc. | Gpr6 inverse agonists |
| WO2026032256A1 (zh) * | 2024-08-06 | 2026-02-12 | 上海齐鲁制药研究中心有限公司 | 单环类gpr6反向激动剂及其用途 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4107288A (en) | 1974-09-18 | 1978-08-15 | Pharmaceutical Society Of Victoria | Injectable compositions, nanoparticles useful therein, and process of manufacturing same |
| US5145684A (en) | 1991-01-25 | 1992-09-08 | Sterling Drug Inc. | Surface modified drug nanoparticles |
| US20070054916A1 (en) | 2004-10-01 | 2007-03-08 | Amgen Inc. | Aryl nitrogen-containing bicyclic compounds and methods of use |
| ZA200801822B (en) | 2005-08-26 | 2009-09-30 | Serono Lab | Pyrazine derivatives and use as p13k inhibitors |
| WO2007125405A2 (en) | 2006-05-01 | 2007-11-08 | Pfizer Products Inc. | Substituted 2-amino-fused heterocyclic compounds |
| UA98141C2 (ru) | 2007-04-11 | 2012-04-25 | Экселиксис, Инк. | Способы лечения с применением хинаксолиновых ингибиторов pi3k-альфа |
| GB0710844D0 (en) | 2007-06-06 | 2007-07-18 | Lectus Therapeutics Ltd | Potassium ion channel modulators & uses thereof |
| JP2010535804A (ja) * | 2007-08-09 | 2010-11-25 | 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 | Ｐｉ３キナーゼ阻害薬としてのキノキサリン誘導体 |
| CN102625804B (zh) | 2009-06-12 | 2015-04-08 | Abivax公司 | 用于治疗aids的化合物 |
| EP2569302A1 (en) * | 2010-05-13 | 2013-03-20 | Amgen, Inc | Heteroaryloxyheterocyclyl compounds as pde10 inhibitors |
| WO2011150156A2 (en) * | 2010-05-26 | 2011-12-01 | Sunovion Pharmaceuticals Inc. | Heteroaryl compounds and methods of use thereof |
| WO2012167423A1 (en) | 2011-06-08 | 2012-12-13 | Hutchison Medipharma Limited | Substituted pyridopyrazines as novel syk inhibitors |
| EP2849849A1 (en) | 2012-05-09 | 2015-03-25 | Ion Beam Applications S.A. | Method for compensating the deviation of a hadron beam produced by a hadron-therapy installation |
| WO2013169964A1 (en) | 2012-05-09 | 2013-11-14 | Sunovion Pharmaceuticals Inc. | Heteroaryl compounds and methods of use thereof |
| US9487526B2 (en) * | 2012-08-13 | 2016-11-08 | Takeda Pharmaceutical Company Limited | Quinoxaline derivatives as GPR6 modulators |
| JO3466B1 (ar) | 2013-12-20 | 2020-07-05 | Takeda Pharmaceuticals Co | مواد ضابطة لتترا هيدرو بيريدوبيرازينات من gpr6 |
-
2013
- 2013-08-13 US US14/421,516 patent/US9487526B2/en active Active
- 2013-08-13 WO PCT/US2013/054715 patent/WO2014028479A1/en not_active Ceased
- 2013-08-13 EP EP13750488.2A patent/EP2882722B1/en active Active
- 2013-08-13 JP JP2015527538A patent/JP6193374B2/ja active Active
-
2016
- 2016-10-25 US US15/334,198 patent/US9770452B2/en active Active
-
2017
- 2017-08-09 JP JP2017154601A patent/JP6389933B2/ja active Active
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