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 (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6193374B2 (ja) * | 2012-08-13 | 2017-09-06 | 武田薬品工業株式会社 | Ｇｐｒ６モジュレーターとしてのキノキサリン誘導体 |
| JO3466B1 (ar) | 2013-12-20 | 2020-07-05 | Takeda Pharmaceuticals Co | مواد ضابطة لتترا هيدرو بيريدوبيرازينات من gpr6 |
| WO2015123505A1 (en) * | 2014-02-14 | 2015-08-20 | Takeda Pharmaceutical Company Limited | Pyridopyrazines modulators of gpr6 |
| JP6484640B2 (ja) * | 2014-02-14 | 2019-03-13 | 武田薬品工業株式会社 | Ｇｐｒ６のピラジンモジュレーター |
| EP3600312B1 (en) * | 2017-03-26 | 2023-05-17 | Takeda Pharmaceutical Company Limited | Piperidinyl- and piperazinyl-substituted heteroaromatic carboxamides as modulators of gpr6 |
| EP4568668A2 (en) * | 2022-08-11 | 2025-06-18 | 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 |
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 |
| EA015937B1 (ru) | 2005-08-26 | 2011-12-30 | Мерк Сероно С.А. | Производные пиразина и их применение в качестве ингибиторов pi3k |
| WO2007125405A2 (en) | 2006-05-01 | 2007-11-08 | Pfizer Products Inc. | Substituted 2-amino-fused heterocyclic compounds |
| HRP20131081T1 (hr) | 2007-04-11 | 2013-12-20 | Exelixis Inc. | Kombinirane terapije koje sadrže hinoksalin inhibitor p13k-alfa za uporabu u lijeäśenju kancera |
| GB0710844D0 (en) | 2007-06-06 | 2007-07-18 | Lectus Therapeutics Ltd | Potassium ion channel modulators & uses thereof |
| EP2173354A4 (en) * | 2007-08-09 | 2011-10-05 | Glaxosmithkline Llc | CHINOXALIN DERIVATIVES AS PI3 KINASE INHIBITORS |
| KR102016889B1 (ko) | 2009-06-12 | 2019-08-30 | 아비박스 | 조기 노화, 구체적으로 조로증을 치료하는데 유용한 화합물 |
| JP2013526546A (ja) * | 2010-05-13 | 2013-06-24 | アムジエン・インコーポレーテツド | Ｐｄｅ１０阻害剤としてのヘテロアリ−ルオキシヘテロシクリル化合物 |
| EP3318561B1 (en) | 2010-05-26 | 2021-12-22 | 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 |
| JP6193374B2 (ja) * | 2012-08-13 | 2017-09-06 | 武田薬品工業株式会社 | Ｇｐｒ６モジュレーターとしてのキノキサリン誘導体 |
| JO3466B1 (ar) | 2013-12-20 | 2020-07-05 | Takeda Pharmaceuticals Co | مواد ضابطة لتترا هيدرو بيريدوبيرازينات من gpr6 |
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2013
- 2013-08-13 JP JP2015527538A patent/JP6193374B2/ja active Active
- 2013-08-13 EP EP13750488.2A patent/EP2882722B1/en active Active
- 2013-08-13 WO PCT/US2013/054715 patent/WO2014028479A1/en not_active Ceased
- 2013-08-13 US US14/421,516 patent/US9487526B2/en active Active
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2016
- 2016-10-25 US US15/334,198 patent/US9770452B2/en active Active
-
2017
- 2017-08-09 JP JP2017154601A patent/JP6389933B2/ja active Active