JP2014518226A5 - - Google Patents
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- Publication number
- JP2014518226A5 JP2014518226A5 JP2014517519A JP2014517519A JP2014518226A5 JP 2014518226 A5 JP2014518226 A5 JP 2014518226A5 JP 2014517519 A JP2014517519 A JP 2014517519A JP 2014517519 A JP2014517519 A JP 2014517519A JP 2014518226 A5 JP2014518226 A5 JP 2014518226A5
- Authority
- JP
- Japan
- Prior art keywords
- drug
- group
- crystalline form
- acetate
- hexane
- 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
- 239000003814 drug Substances 0.000 description 7
- 229940079593 drug Drugs 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000001069 Raman spectroscopy Methods 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
- PFCHFHIRKBAQGU-UHFFFAOYSA-N 3-hexanone Chemical compound CCCC(=O)CC PFCHFHIRKBAQGU-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11005587 | 2011-07-08 | ||
| EP11005587.8 | 2011-07-08 | ||
| PCT/EP2012/002839 WO2013007361A1 (en) | 2011-07-08 | 2012-07-06 | Crystalline (1r,4r)-6'-fluoro-n,n-dimethyl-4-phenyl-4',9'-dihydro-3'h-spiro[cyclohexane-1,1'-pyrano[3,4,b]indol]-4-amine |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017003194A Division JP6559165B2 (ja) | 2011-07-08 | 2017-01-12 | 結晶性（１ｒ，４ｒ）−６’−フルオロ−Ｎ，Ｎ−ジメチル−４−フェニル−４’，９’−ジヒドロ−３’Ｈ−スピロ［シクロヘキサン−１，１’−ピラノ［３，４，ｂ］インドール］−４−アミン |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014518226A JP2014518226A (ja) | 2014-07-28 |
| JP2014518226A5 true JP2014518226A5 (cg-RX-API-DMAC10.html) | 2015-11-05 |
| JP6276689B2 JP6276689B2 (ja) | 2018-02-07 |
Family
ID=46717800
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014517519A Active JP6276689B2 (ja) | 2011-07-08 | 2012-07-06 | 結晶性（１ｒ，４ｒ）−６’−フルオロ−Ｎ，Ｎ−ジメチル−４−フェニル−４’，９’−ジヒドロ−３’Ｈ−スピロ［シクロヘキサン−１，１’−ピラノ［３，４，ｂ］インドール］−４−アミン |
| JP2017003194A Active JP6559165B2 (ja) | 2011-07-08 | 2017-01-12 | 結晶性（１ｒ，４ｒ）−６’−フルオロ−Ｎ，Ｎ−ジメチル−４−フェニル−４’，９’−ジヒドロ−３’Ｈ−スピロ［シクロヘキサン−１，１’−ピラノ［３，４，ｂ］インドール］−４−アミン |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017003194A Active JP6559165B2 (ja) | 2011-07-08 | 2017-01-12 | 結晶性（１ｒ，４ｒ）−６’−フルオロ−Ｎ，Ｎ−ジメチル−４−フェニル−４’，９’−ジヒドロ−３’Ｈ−スピロ［シクロヘキサン−１，１’−ピラノ［３，４，ｂ］インドール］−４−アミン |
Country Status (23)
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8618156B2 (en) * | 2011-07-08 | 2013-12-31 | Gruenenthal Gmbh | Crystalline (1r,4r)-6'-fluoro-N,N-dimethyl-4-phenyl-4',9'-dihydro-3'H-spiro[cyclohexane-1,1'-pyrano[3,4,b]indol]-4-amine |
| CN107427493A (zh) | 2015-01-23 | 2017-12-01 | 格吕伦塔尔有限公司 | 用于治疗肝功能受损和/或肾功能受损的受试者的疼痛的Cebranopadol |
| US20180021304A1 (en) | 2015-02-02 | 2018-01-25 | Ratiopharm Gmbh | Composition comprising cebranopadol in a dissolved form |
| MX2018010367A (es) | 2016-02-29 | 2018-12-10 | Guenenthal Gmbh | Titulacion de cebranopadol. |
| JP7365073B2 (ja) * | 2019-05-21 | 2023-10-19 | ジァンスー フォアフロント ファーマシューティカル カンパニー，リミテッド | トレプロスチニルナトリウムの新規な結晶形および製造方法 |
| CN112254496A (zh) * | 2020-09-25 | 2021-01-22 | 榆林学院 | 一种煤泥收集装置 |
| WO2024129782A1 (en) | 2022-12-12 | 2024-06-20 | Park Therapeutics, Inc. | Regimens and compositions useful for alleviating pain |
| CN122458986A (zh) | 2023-02-15 | 2026-07-24 | 艾德神经立治疗公司 | 有用于缓解疼痛的方案和组合物 |
| WO2026035694A1 (en) | 2024-08-05 | 2026-02-12 | Adneuris Therapeutics, Inc. | Cebranopadol useful for preventing or reducing opioid induced respiratory depression |
| WO2026161433A1 (en) | 2025-01-21 | 2026-07-30 | Adneuris Therapeutics, Inc. | Cebranopadol useful for alleviating pain |
| WO2026161842A1 (en) | 2025-01-27 | 2026-07-30 | Adneuris Therapeutics, Inc. | Cebranopadol useful for treating pain |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10252667A1 (de) | 2002-11-11 | 2004-05-27 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
| DE102005016460A1 (de) * | 2005-04-11 | 2006-10-19 | Grünenthal GmbH | Spriocyclische Cyclohexanderivate zur Behandlung von Substanzabhängigkeit |
| DE102006033109A1 (de) * | 2006-07-18 | 2008-01-31 | Grünenthal GmbH | Substituierte Heteroaryl-Derivate |
| DE102006046745A1 (de) | 2006-09-29 | 2008-04-03 | Grünenthal GmbH | Gemischte ORL1/µ-Agonisten zur Behandlung von Schmerz |
| EP3459533A1 (en) * | 2010-08-04 | 2019-03-27 | Grünenthal GmbH | Pharmaceutical dosage form comprising 6'-fluoro-(n-methyl- or n,n-dimethyl-)-4-phenyl-4',9'-dihydro-3'h-spiro[cyclohexane-1,1'-pyrano[3,4,b]indol]-4-amine for the treatment of nociceptive pain |
| US8618156B2 (en) * | 2011-07-08 | 2013-12-31 | Gruenenthal Gmbh | Crystalline (1r,4r)-6'-fluoro-N,N-dimethyl-4-phenyl-4',9'-dihydro-3'H-spiro[cyclohexane-1,1'-pyrano[3,4,b]indol]-4-amine |
-
2012
- 2012-07-06 US US13/542,809 patent/US8618156B2/en active Active
- 2012-07-06 RS RS20170921A patent/RS56343B1/sr unknown
- 2012-07-06 AU AU2012283449A patent/AU2012283449B2/en not_active Ceased
- 2012-07-06 EA EA201400120A patent/EA026750B1/ru not_active IP Right Cessation
- 2012-07-06 PL PL12748646T patent/PL2729470T3/pl unknown
- 2012-07-06 AR ARP120102454A patent/AR087081A1/es not_active Application Discontinuation
- 2012-07-06 BR BR112014000358A patent/BR112014000358A2/pt not_active IP Right Cessation
- 2012-07-06 PT PT127486462T patent/PT2729470T/pt unknown
- 2012-07-06 MX MX2014000297A patent/MX2014000297A/es unknown
- 2012-07-06 SI SI201231030T patent/SI2729470T1/sl unknown
- 2012-07-06 DK DK12748646.2T patent/DK2729470T3/en active
- 2012-07-06 LT LTEP12748646.2T patent/LT2729470T/lt unknown
- 2012-07-06 CN CN201710173425.6A patent/CN106939005A/zh active Pending
- 2012-07-06 TW TW101124343A patent/TWI585092B/zh not_active IP Right Cessation
- 2012-07-06 ES ES12748646.2T patent/ES2641299T3/es active Active
- 2012-07-06 WO PCT/EP2012/002839 patent/WO2013007361A1/en not_active Ceased
- 2012-07-06 CN CN201280032432.XA patent/CN103649094B/zh active Active
- 2012-07-06 HR HRP20170968TT patent/HRP20170968T1/hr unknown
- 2012-07-06 DK DK17020200.6T patent/DK3235821T3/da active
- 2012-07-06 HU HUE12748646A patent/HUE033043T2/hu unknown
- 2012-07-06 CA CA2841032A patent/CA2841032C/en active Active
- 2012-07-06 EP EP12748646.2A patent/EP2729470B1/en active Active
- 2012-07-06 JP JP2014517519A patent/JP6276689B2/ja active Active
- 2012-07-06 EP EP17020200.6A patent/EP3235821B1/en active Active
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2013
- 2013-03-15 US US13/835,298 patent/US8765800B2/en active Active
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2014
- 2014-01-06 IL IL230331A patent/IL230331B/en unknown
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2017
- 2017-01-12 JP JP2017003194A patent/JP6559165B2/ja active Active
- 2017-07-04 AU AU2017204572A patent/AU2017204572B2/en not_active Ceased
- 2017-08-02 CY CY20171100830T patent/CY1120525T1/el unknown