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 (https=) | 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)
| Country | Link |
|---|---|
| US (2) | US8618156B2 (https=) |
| EP (2) | EP3235821B1 (https=) |
| JP (2) | JP6276689B2 (https=) |
| CN (2) | CN103649094B (https=) |
| AR (1) | AR087081A1 (https=) |
| AU (2) | AU2012283449B2 (https=) |
| BR (1) | BR112014000358A2 (https=) |
| CA (1) | CA2841032C (https=) |
| CY (1) | CY1120525T1 (https=) |
| DK (2) | DK2729470T3 (https=) |
| EA (1) | EA026750B1 (https=) |
| ES (1) | ES2641299T3 (https=) |
| HR (1) | HRP20170968T1 (https=) |
| HU (1) | HUE033043T2 (https=) |
| IL (1) | IL230331B (https=) |
| LT (1) | LT2729470T (https=) |
| MX (1) | MX2014000297A (https=) |
| PL (1) | PL2729470T3 (https=) |
| PT (1) | PT2729470T (https=) |
| RS (1) | RS56343B1 (https=) |
| SI (1) | SI2729470T1 (https=) |
| TW (1) | TWI585092B (https=) |
| WO (1) | WO2013007361A1 (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103649094B (zh) * | 2011-07-08 | 2017-05-24 | 格吕伦塔尔有限公司 | 晶态的(1r,4r)‑6’‑氟‑N,N‑二甲基‑4‑苯基‑4’,9’‑二氢‑3’H‑螺[环己烷‑1,1’‑吡喃并[3,4,b]吲哚]‑4‑胺 |
| JP6673924B2 (ja) | 2015-01-23 | 2020-03-25 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | 肝機能障害および／または腎機能障害を有する対象における疼痛を治療するためのセブラノパドール |
| EP3253374B1 (en) | 2015-02-02 | 2018-11-28 | ratiopharm GmbH | Composition comprising cebranopadol in a dissolved form |
| JP7373904B2 (ja) | 2016-02-29 | 2023-11-06 | パーク・セラピューティクス・インコーポレイテッド | セブラノパドールの滴定 |
| CN112313202A (zh) * | 2019-05-21 | 2021-02-02 | 江苏众强药业有限公司 | 曲前列尼尔钠盐新晶型及制备方法 |
| 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 |
| EP4665333A1 (en) | 2023-02-15 | 2025-12-24 | Adneuris Therapeutics, Inc. | Regimens and compositions useful for alleviating pain |
| WO2026035694A1 (en) | 2024-08-05 | 2026-02-12 | Adneuris Therapeutics, Inc. | Cebranopadol useful for preventing or reducing opioid induced respiratory depression |
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 |
| KR20130097173A (ko) * | 2010-08-04 | 2013-09-02 | 그뤼넨탈 게엠베하 | 신경병증성 통증을 치료하기 위한 ６’플루오로（Ｎ메틸 또는 Ｎ，Ｎ디메틸）４페닐４’，９’디하이드로３’Ｈ스피로[사이클로헥산１，１’피라노[３，４，ｂ]인돌]４아민을 포함하는 약제학적 투여형 |
| CN103649094B (zh) * | 2011-07-08 | 2017-05-24 | 格吕伦塔尔有限公司 | 晶态的(1r,4r)‑6’‑氟‑N,N‑二甲基‑4‑苯基‑4’,9’‑二氢‑3’H‑螺[环己烷‑1,1’‑吡喃并[3,4,b]吲哚]‑4‑胺 |
-
2012
- 2012-07-06 CN CN201280032432.XA patent/CN103649094B/zh active Active
- 2012-07-06 US US13/542,809 patent/US8618156B2/en active Active
- 2012-07-06 ES ES12748646.2T patent/ES2641299T3/es active Active
- 2012-07-06 EP EP17020200.6A patent/EP3235821B1/en active Active
- 2012-07-06 MX MX2014000297A patent/MX2014000297A/es unknown
- 2012-07-06 WO PCT/EP2012/002839 patent/WO2013007361A1/en not_active Ceased
- 2012-07-06 AR ARP120102454A patent/AR087081A1/es not_active Application Discontinuation
- 2012-07-06 RS RS20170921A patent/RS56343B1/sr unknown
- 2012-07-06 TW TW101124343A patent/TWI585092B/zh not_active IP Right Cessation
- 2012-07-06 EA EA201400120A patent/EA026750B1/ru not_active IP Right Cessation
- 2012-07-06 DK DK12748646.2T patent/DK2729470T3/en active
- 2012-07-06 PT PT127486462T patent/PT2729470T/pt unknown
- 2012-07-06 PL PL12748646T patent/PL2729470T3/pl unknown
- 2012-07-06 BR BR112014000358A patent/BR112014000358A2/pt not_active IP Right Cessation
- 2012-07-06 CN CN201710173425.6A patent/CN106939005A/zh active Pending
- 2012-07-06 JP JP2014517519A patent/JP6276689B2/ja active Active
- 2012-07-06 CA CA2841032A patent/CA2841032C/en active Active
- 2012-07-06 HR HRP20170968TT patent/HRP20170968T1/hr unknown
- 2012-07-06 AU AU2012283449A patent/AU2012283449B2/en not_active Ceased
- 2012-07-06 EP EP12748646.2A patent/EP2729470B1/en active Active
- 2012-07-06 HU HUE12748646A patent/HUE033043T2/hu unknown
- 2012-07-06 LT LTEP12748646.2T patent/LT2729470T/lt unknown
- 2012-07-06 DK DK17020200.6T patent/DK3235821T3/da active
- 2012-07-06 SI SI201231030T patent/SI2729470T1/sl unknown
-
2013
- 2013-03-15 US US13/835,298 patent/US8765800B2/en active Active
-
2014
- 2014-01-06 IL IL230331A patent/IL230331B/en unknown
-
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
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