JP2016510320A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2016510320A5 JP2016510320A5 JP2015551836A JP2015551836A JP2016510320A5 JP 2016510320 A5 JP2016510320 A5 JP 2016510320A5 JP 2015551836 A JP2015551836 A JP 2015551836A JP 2015551836 A JP2015551836 A JP 2015551836A JP 2016510320 A5 JP2016510320 A5 JP 2016510320A5
- Authority
- JP
- Japan
- Prior art keywords
- optionally substituted
- compound
- formula
- alkyl
- 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.)
- Ceased
Links
- 150000001875 compounds Chemical class 0.000 claims description 102
- 150000003839 salts Chemical class 0.000 claims description 50
- 229910052739 hydrogen Inorganic materials 0.000 claims description 48
- 239000001257 hydrogen Substances 0.000 claims description 48
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 48
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- 125000001188 haloalkyl group Chemical group 0.000 claims description 28
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 22
- 125000002947 alkylene group Chemical group 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 20
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 17
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 17
- 125000000623 heterocyclic group Chemical group 0.000 claims description 17
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 17
- 125000003107 substituted aryl group Chemical group 0.000 claims description 17
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 17
- 125000001475 halogen functional group Chemical group 0.000 claims description 15
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 201000010099 disease Diseases 0.000 claims description 11
- 208000035475 disorder Diseases 0.000 claims description 11
- 208000023275 Autoimmune disease Diseases 0.000 claims description 6
- -1 3-methoxy-5-methylphenyl Chemical group 0.000 claims description 5
- 241000124008 Mammalia Species 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000004043 oxo group Chemical group O=* 0.000 claims description 5
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 5
- 101000616502 Homo sapiens Phosphatidylinositol 3,4,5-trisphosphate 5-phosphatase 1 Proteins 0.000 claims description 4
- 102100021797 Phosphatidylinositol 3,4,5-trisphosphate 5-phosphatase 1 Human genes 0.000 claims description 4
- 230000001613 neoplastic effect Effects 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 230000002062 proliferating effect Effects 0.000 claims description 3
- QLDWKJIFTFHGHX-IBRRDTTFSA-N (1r,2r,8as)-1-[(3,5-dimethoxyphenyl)sulfonylmethyl]-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1h-naphthalen-2-ol Chemical compound COC1=CC(OC)=CC(S(=O)(=O)C[C@@H]2[C@]3(CCCC(C)(C)C3CC[C@]2(O)C)C)=C1 QLDWKJIFTFHGHX-IBRRDTTFSA-N 0.000 claims description 2
- BKARYMOMZUJSFB-PABCKOPISA-N (1s,2r,4as,8as)-1-[(3,5-dimethoxyphenoxy)methyl]-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1h-naphthalen-2-ol Chemical compound COC1=CC(OC)=CC(OC[C@@H]2[C@]3(CCCC(C)(C)[C@@H]3CC[C@]2(O)C)C)=C1 BKARYMOMZUJSFB-PABCKOPISA-N 0.000 claims description 2
- FNOGLPRPGFTFMV-PABCKOPISA-N (1s,2r,4as,8as)-1-[(3-methoxy-5-methylphenoxy)methyl]-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1h-naphthalen-2-ol Chemical compound COC1=CC(C)=CC(OC[C@@H]2[C@]3(CCCC(C)(C)[C@@H]3CC[C@]2(O)C)C)=C1 FNOGLPRPGFTFMV-PABCKOPISA-N 0.000 claims description 2
- CWDHVPLOTPEQSW-AEZNDSDVSA-N (1s,2r,4as,8as)-1-[[3,5-di(propan-2-yloxy)phenoxy]methyl]-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1h-naphthalen-2-ol Chemical compound CC(C)OC1=CC(OC(C)C)=CC(OC[C@@H]2[C@]3(CCCC(C)(C)[C@@H]3CC[C@]2(O)C)C)=C1 CWDHVPLOTPEQSW-AEZNDSDVSA-N 0.000 claims description 2
- NQIZWULAGUBAPT-QNWVGRARSA-N (4as,8s,8as)-8-[(3-methoxy-5-methylphenyl)methyl]-4,4,8a-trimethyl-7-methylidene-2,3,4a,5,6,8-hexahydro-1h-naphthalene Chemical compound COC1=CC(C)=CC(C[C@@H]2[C@]3(CCCC(C)(C)[C@@H]3CCC2=C)C)=C1 NQIZWULAGUBAPT-QNWVGRARSA-N 0.000 claims description 2
- CFWXECSSWZJSRE-AWWSKVOZSA-N [(1r,3r,4as,8as)-3-hydroxy-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1h-naphthalen-1-yl]-(3,5-dimethoxyphenyl)methanone Chemical compound COC1=CC(OC)=CC(C(=O)[C@@H]2[C@]3(CCCC(C)(C)[C@@H]3C[C@@H](O)C2=C)C)=C1 CFWXECSSWZJSRE-AWWSKVOZSA-N 0.000 claims description 2
- VYYRCVDIRXFGAJ-FLDDEYDQSA-N n-[(2r,3s,4s,4as)-4-[(furan-2-carbonylamino)methyl]-3,4a,8,8-tetramethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]-4-methylpiperazine-1-carboxamide Chemical compound C([C@@H]1[C@@]2(C)CCCC(C)(C)C2C[C@H]([C@H]1C)NC(=O)N1CCN(C)CC1)NC(=O)C1=CC=CO1 VYYRCVDIRXFGAJ-FLDDEYDQSA-N 0.000 claims description 2
- QWTDZGGOZRPXJQ-WEYNBAESSA-N n-[(2r,3s,4s,4as)-4-[(furan-2-carbonylamino)methyl]-3,4a,8,8-tetramethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]pyridine-3-carboxamide Chemical compound C([C@@H]1[C@@]2(C)CCCC(C)(C)C2C[C@H]([C@H]1C)NC(=O)C=1C=NC=CC=1)NC(=O)C1=CC=CO1 QWTDZGGOZRPXJQ-WEYNBAESSA-N 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- FXKZQMYOBJXFRZ-COXDHOHBSA-N n-[(2r,3s,4s,4ar)-4-[2-(furan-2-carbonylamino)ethyl]-3,4a,8,8-tetramethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]-4-methylpiperazine-1-carboxamide Chemical compound C([C@@H]1[C@@]2(C)CCCC(C)(C)C2C[C@H]([C@H]1C)NC(=O)N1CCN(C)CC1)CNC(=O)C1=CC=CO1 FXKZQMYOBJXFRZ-COXDHOHBSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 208000027866 inflammatory disease Diseases 0.000 description 4
- WELDKLQNVRHBJE-PABCKOPISA-N (1r,2r,4as,8as)-1-[(3-methoxy-5-methylphenyl)methyl]-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1h-naphthalen-2-ol Chemical compound COC1=CC(C)=CC(C[C@@H]2[C@]3(CCCC(C)(C)[C@@H]3CC[C@]2(O)C)C)=C1 WELDKLQNVRHBJE-PABCKOPISA-N 0.000 description 1
- UBJNOBWQEIATMV-YUVXSKOASA-N (1r,2r,4as,8as)-1-[(3-methoxyphenyl)sulfanylmethyl]-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1h-naphthalen-2-ol Chemical compound COC1=CC=CC(SC[C@@H]2[C@]3(CCCC(C)(C)[C@@H]3CC[C@]2(O)C)C)=C1 UBJNOBWQEIATMV-YUVXSKOASA-N 0.000 description 1
- DAAIATWKXYUMJJ-IHFIDZABSA-N (1s,2s,4as,8ar)-1-[2-(3-methoxyphenyl)ethyl]-5,5,8a-trimethyl-1,2,3,4,4a,6,7,8-octahydronaphthalene-2-carboxylic acid Chemical compound COC1=CC=CC(CC[C@@H]2[C@]3(CCCC(C)(C)[C@@H]3CC[C@@H]2C(O)=O)C)=C1 DAAIATWKXYUMJJ-IHFIDZABSA-N 0.000 description 1
- KDBULFZZDBNXOL-UHFFFAOYSA-N 1-[(3,5-dimethoxyphenyl)-hydroxymethyl]-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1h-naphthalen-2-ol Chemical compound COC1=CC(OC)=CC(C(O)C2C3(CCCC(C)(C)C3CCC2(O)C)C)=C1 KDBULFZZDBNXOL-UHFFFAOYSA-N 0.000 description 1
- ONFMXWUOLIIOHB-LCKKVJLRSA-N [(1s,2s,4as,8ar)-1-[2-(3-methoxyphenyl)ethyl]-5,5,8a-trimethyl-1,2,3,4,4a,6,7,8-octahydronaphthalen-2-yl]methanol Chemical compound COC1=CC=CC(CC[C@@H]2[C@]3(CCCC(C)(C)[C@@H]3CC[C@@H]2CO)C)=C1 ONFMXWUOLIIOHB-LCKKVJLRSA-N 0.000 description 1
- NELLCJAWIJGSOS-LVRVKJESSA-N [(4as,8as)-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]-(3-methoxy-5-methylphenyl)methanol Chemical compound COC1=CC(C)=CC(C(O)C=2[C@]3(CCCC(C)(C)[C@@H]3CCC=2C)C)=C1 NELLCJAWIJGSOS-LVRVKJESSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361750695P | 2013-01-09 | 2013-01-09 | |
| US61/750,695 | 2013-01-09 | ||
| PCT/US2014/010501 WO2014110036A1 (en) | 2013-01-09 | 2014-01-07 | Ship1 modulators and methods related thereto |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018042934A Division JP6526275B2 (ja) | 2013-01-09 | 2018-03-09 | Ｓｈｉｐ１モジュレーターおよびそれに関連する方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2016510320A JP2016510320A (ja) | 2016-04-07 |
| JP2016510320A5 true JP2016510320A5 (https=) | 2017-01-12 |
Family
ID=50033793
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015551836A Ceased JP2016510320A (ja) | 2013-01-09 | 2014-01-07 | Ｓｈｉｐ１モジュレーターおよびそれに関連する方法 |
| JP2018042934A Expired - Fee Related JP6526275B2 (ja) | 2013-01-09 | 2018-03-09 | Ｓｈｉｐ１モジュレーターおよびそれに関連する方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018042934A Expired - Fee Related JP6526275B2 (ja) | 2013-01-09 | 2018-03-09 | Ｓｈｉｐ１モジュレーターおよびそれに関連する方法 |
Country Status (14)
| Country | Link |
|---|---|
| US (3) | US9540353B2 (https=) |
| EP (1) | EP2943470A1 (https=) |
| JP (2) | JP2016510320A (https=) |
| KR (1) | KR20150106895A (https=) |
| CN (2) | CN108752236A (https=) |
| AU (2) | AU2014205587B2 (https=) |
| BR (1) | BR112015016206A2 (https=) |
| CA (1) | CA2896559A1 (https=) |
| HK (1) | HK1216886A1 (https=) |
| IL (1) | IL239659A0 (https=) |
| MX (1) | MX2015008873A (https=) |
| RU (1) | RU2015133177A (https=) |
| WO (1) | WO2014110036A1 (https=) |
| ZA (1) | ZA201504477B (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014110036A1 (en) | 2013-01-09 | 2014-07-17 | Aquinox Pharmaceuticals Inc. | Ship1 modulators and methods related thereto |
| WO2018126040A1 (en) | 2016-12-28 | 2018-07-05 | Aquinox Pharmaceuticals (Canada) Inc. | Crystalline solid forms of (1s,3s,4r)-4-((3as,4r,5s,7as)-4- (aminomethyl)-7a-methyl-1-methyleneoctahydro-1h-inden-5-yl)-3- (hydroxymethyl)-4-methylcyclohexanol |
| CN107602496B (zh) * | 2017-09-08 | 2020-10-13 | 南京农业大学 | 手性补身烷基杂环类化合物及其作为杀菌剂的用途 |
| WO2019195777A1 (en) | 2018-04-06 | 2019-10-10 | Aquinox Pharmaceuticals (Canada) Inc. | Indene derivatives useful in treating pain and inflammation |
| WO2019195692A1 (en) | 2018-04-06 | 2019-10-10 | Aquinox Pharmaceuticals (Canada) Inc. | Hexadecahydro-1h-cyclopenta[a]phenanthrene derivatives useful in treating pain and inflammation |
| EP3774746A1 (en) | 2018-04-06 | 2021-02-17 | Aquinox Pharmaceuticals (Canada) Inc. | Indene derivatives useful in treating pain and inflammation |
| WO2024220556A2 (en) * | 2023-04-20 | 2024-10-24 | Hb Therapeutics, Inc. | Heterocyclic sumo1 small molecule degraders and use thereof |
| CN116554063B (zh) * | 2023-05-23 | 2025-03-07 | 江苏省农用激素工程技术研究中心有限公司 | 氟胺磺隆中间体的制备方法 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002179564A (ja) | 1998-04-14 | 2002-06-26 | Toagosei Co Ltd | 抗真菌剤 |
| JPH11349478A (ja) * | 1998-06-03 | 1999-12-21 | Toagosei Co Ltd | 抗癌剤 |
| JP2001031663A (ja) * | 1999-07-14 | 2001-02-06 | Toagosei Co Ltd | エポキシ化合物およびその誘導体 |
| JP2001048873A (ja) * | 1999-08-10 | 2001-02-20 | Toagosei Co Ltd | エポキシ化合物およびその誘導体 |
| WO2003033517A1 (en) | 2001-10-17 | 2003-04-24 | The University Of British Columbia | Ship 1 modulators |
| WO2004035601A1 (en) | 2002-10-17 | 2004-04-29 | The University Of British Columbia | Ship 1 modulators |
| CA2521883C (en) | 2003-04-15 | 2013-09-17 | Inflazyme Pharmaceuticals Ltd. | Indene derivatives as pharmaceutical agents |
| JP2009541224A (ja) * | 2006-06-21 | 2009-11-26 | ザ・ユニバーシティ・オブ・ブリティッシュ・コロンビア | Ｓｈｉｐ１モジュレーター化合物 |
| RU2385863C2 (ru) | 2008-04-21 | 2010-04-10 | Новосибирский институт органической химии им. Н.Н. Ворожцова Сибирского отделения Российской академии наук (НИОХ СО РАН) (статус государственного учреждения) | N-ЗАМЕЩЕННЫЕ (1S,4aR,5S)-МЕТИЛ-5-[2-(2'-ОКСО-2',5'-ДИГИДРО-1Н-ПИРРОЛ-3'-ИЛ)ЭТИЛ]-1,4a-ДИМЕТИЛ-6-МЕТИЛЕНДЕКАГИДРОНАФТАЛИН-1-КАРБОКСИЛАТЫ, ОБЛАДАЮЩИЕ ПРОТИВОСУДОРОЖНОЙ АКТИВНОСТЬЮ |
| US8101605B2 (en) * | 2009-12-04 | 2012-01-24 | Aquinox Pharmaceuticals Inc. | SHIP1 modulators and methods related thereto |
| US9000050B2 (en) | 2010-08-20 | 2015-04-07 | The University Of British Columbia | SHIP1 modulators and related methods |
| WO2014110036A1 (en) | 2013-01-09 | 2014-07-17 | Aquinox Pharmaceuticals Inc. | Ship1 modulators and methods related thereto |
| MX2015012111A (es) | 2013-03-14 | 2016-05-05 | Aquinox Pharmaceuticals Canada Inc | Moduladores de ship1 y métodos relacionados con éstos. |
| US10100056B2 (en) | 2013-03-14 | 2018-10-16 | Aquinox Pharmaceuticals (Canada) Inc. | SHIP1 modulators and methods related thereto |
| US9944590B2 (en) | 2015-06-26 | 2018-04-17 | Aquinox Pharmaceuticals (Canada) Inc. | Crystalline solid forms of the acetate salt of (1S,3S,4R)-4-((3aS,4R,5S,7aS)-4-(aminomethyl)-7a-methyl-1-methyleneoctahydro-1H-inden-5-yl)-3-(hydroxymethyl)-4-methylcyclohexanol |
| US10053415B2 (en) | 2016-01-20 | 2018-08-21 | Aquinox Pharmaceuticals (Canada) Inc. | Synthesis of a substituted indene derivative |
-
2014
- 2014-01-07 WO PCT/US2014/010501 patent/WO2014110036A1/en not_active Ceased
- 2014-01-07 BR BR112015016206A patent/BR112015016206A2/pt not_active Application Discontinuation
- 2014-01-07 HK HK16104760.2A patent/HK1216886A1/zh unknown
- 2014-01-07 US US14/759,622 patent/US9540353B2/en not_active Expired - Fee Related
- 2014-01-07 AU AU2014205587A patent/AU2014205587B2/en not_active Ceased
- 2014-01-07 CN CN201810436062.5A patent/CN108752236A/zh active Pending
- 2014-01-07 CN CN201480013140.0A patent/CN105026375B/zh not_active Expired - Fee Related
- 2014-01-07 EP EP14702673.6A patent/EP2943470A1/en not_active Withdrawn
- 2014-01-07 JP JP2015551836A patent/JP2016510320A/ja not_active Ceased
- 2014-01-07 KR KR1020157021150A patent/KR20150106895A/ko not_active Ceased
- 2014-01-07 RU RU2015133177A patent/RU2015133177A/ru not_active Application Discontinuation
- 2014-01-07 MX MX2015008873A patent/MX2015008873A/es unknown
- 2014-01-07 CA CA2896559A patent/CA2896559A1/en not_active Abandoned
-
2015
- 2015-06-22 ZA ZA2015/04477A patent/ZA201504477B/en unknown
- 2015-06-25 IL IL239659A patent/IL239659A0/en unknown
-
2016
- 2016-12-06 US US15/370,973 patent/US9937167B2/en not_active Expired - Fee Related
-
2018
- 2018-01-30 US US15/884,044 patent/US10272081B2/en not_active Expired - Fee Related
- 2018-03-09 JP JP2018042934A patent/JP6526275B2/ja not_active Expired - Fee Related
- 2018-08-23 AU AU2018220093A patent/AU2018220093A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2016510320A5 (https=) | ||
| WO2014110036A4 (en) | Ship1 modulators and methods related thereto | |
| RU2460730C2 (ru) | Новые производные n-(8-гетероарилтетрагидронафталин-2-ил)-или n-(5-гетероарилхроман-3-ил)-карбоксамида для лечения боли | |
| CY1123270T1 (el) | Υποκατεστημενες ενωσεις βενζαλδεϋδης και μεθοδοι για τη χρηση τους στην αυξηση της οξυγονωσης των ιστων | |
| JP2018135335A5 (https=) | ||
| JP2014507455A5 (https=) | ||
| RU2015123738A (ru) | Ингибиторы котранспортера натрий-глюкозы 1 | |
| JP2014051526A5 (https=) | ||
| JP2017505293A5 (https=) | ||
| JP2012522056A5 (https=) | ||
| JP2012532136A5 (https=) | ||
| JP2014511891A5 (https=) | ||
| RU2020107039A (ru) | Спироциклические соединения и способы их получения и применения | |
| RU2503663C2 (ru) | Мостиковые шестичленные циклические соединения | |
| JP2014506907A5 (https=) | ||
| JP2014534981A5 (https=) | ||
| JP2016517409A5 (https=) | ||
| RU2013140169A (ru) | Противоопухолевое терапевтическое средство | |
| RU2010154400A (ru) | Гетероциклическое соединение | |
| EP2607363A4 (en) | CONDENSED RING COMPOUND FOR USE AS MINERALOCORTICOID RECEPTOR ANTAGONISTS | |
| JP2012518634A5 (https=) | ||
| JP2016540811A5 (https=) | ||
| RU2017117566A (ru) | Активатор kcnq2-5 каналов | |
| JP2016528273A5 (https=) | ||
| RU2016104844A (ru) | Производные n-мочевино замещенных аминокислот как модуляторы формил-пептидного рецептора |