HRP20161105T1 - KRUTI OBLICI (1R,4R)-6'-FLUORO-N,N-DIMETIL-4-FENIL-4',9'-DIHIDRO-3'H-SPIRO[CIKLOHEKSAN-1,1'-PIRANO[3,4,b]INDOL]-4-AMINA I SUMPORNE KISELINE - Google Patents
KRUTI OBLICI (1R,4R)-6'-FLUORO-N,N-DIMETIL-4-FENIL-4',9'-DIHIDRO-3'H-SPIRO[CIKLOHEKSAN-1,1'-PIRANO[3,4,b]INDOL]-4-AMINA I SUMPORNE KISELINE Download PDFInfo
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- HRP20161105T1 HRP20161105T1 HRP20161105TT HRP20161105T HRP20161105T1 HR P20161105 T1 HRP20161105 T1 HR P20161105T1 HR P20161105T T HRP20161105T T HR P20161105TT HR P20161105 T HRP20161105 T HR P20161105T HR P20161105 T1 HRP20161105 T1 HR P20161105T1
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- Prior art keywords
- fluoro
- pyrano
- spiro
- dihydro
- dimethyl
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- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title claims 25
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 title claims 18
- 239000007787 solid Substances 0.000 title claims 11
- 230000005855 radiation Effects 0.000 claims 11
- 238000001069 Raman spectroscopy Methods 0.000 claims 9
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 9
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 9
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 6
- 238000002441 X-ray diffraction Methods 0.000 claims 6
- 239000013078 crystal Substances 0.000 claims 5
- 238000000634 powder X-ray diffraction Methods 0.000 claims 5
- 239000002904 solvent Substances 0.000 claims 3
- 238000000113 differential scanning calorimetry Methods 0.000 claims 2
- 239000012458 free base Substances 0.000 claims 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- 238000000926 separation method Methods 0.000 claims 2
- 239000000725 suspension Substances 0.000 claims 2
- MXTYSYXDDDVPBQ-UHFFFAOYSA-N 2-(5-fluoro-1h-indol-3-yl)ethanol Chemical compound C1=C(F)C=C2C(CCO)=CNC2=C1 MXTYSYXDDDVPBQ-UHFFFAOYSA-N 0.000 claims 1
- DEOPEYZZVGZQFC-UHFFFAOYSA-N 4-(dimethylamino)-4-phenylcyclohexan-1-one Chemical compound C=1C=CC=CC=1C1(N(C)C)CCC(=O)CC1 DEOPEYZZVGZQFC-UHFFFAOYSA-N 0.000 claims 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 230000008021 deposition Effects 0.000 claims 1
- 238000004090 dissolution Methods 0.000 claims 1
- 238000001704 evaporation Methods 0.000 claims 1
- 230000008020 evaporation Effects 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 238000002156 mixing Methods 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 238000001556 precipitation Methods 0.000 claims 1
- 239000012429 reaction media Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
- C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Indole Compounds (AREA)
Claims (16)
1. Kruti oblik (1r,4r)-6'-fluoro-N,N-dimetil-4-fenil-4',9'-dihidro-3'H-spiro[ciklo-heksan-1,1'-pirano[3,4,b]indol]-4-amina i sumporne kiseline.
2. Kruti oblik prema zahtjevu 1, naznačen time da je kruti oblik (1r,4r)-6'-fluoro-N,N-dimetil-4-fenil-4',9'-dihidro-3'H-spiro[cikloheksan-1,1'-pirano[3,4,b]indol]-4-amin sulfat ili (1r,4r)-6'-fluoro-N,N-dimetil-4-fenil-4',9'-dihidro-3'H-spiro[ciklo-heksan-1,1'-pirano[3,4,b]indol]-4-amin hemi-sulfat.
3. Kruti oblik prema zahtjevu 1 ili 2, naznačen time da je kristalni oblik ili amorfni oblik.
4. Kristalni oblik prema bilo kojem od prethodnih zahtjeva, naznačen time da ima jedan ili više vrhova difrakcije X-zraka (CuKα zračenje) koji su odabrani iz skupine koju čine 9.7 ±1.0 (2Θ), 17.7 ±1.0 (2Θ), 18.2 ±1.0 (2Θ) i 25.7 ±1.0 (2Θ), i/ili jedna ili više Ramanovih vrpci kod 916±5 cm-1, 1002 ±5 cm-1, 1028 ±5 cm-1, 1569±5 cm-1, 1583±5 cm-1, 2980 ±5 cm-1 i/ili kod 3076 ±5 cm-1.
5. Kristalni oblik prema bilo kojem od prethodnih zahtjeva, naznačen time da je ansolvat ili solvat.
6. Kristalni oblik prema bilo kojem od prethodnih zahtjeva, naznačen time da ima
A: vrhove difrakcije X-zraka (CuKα zračenje) kod 7.3 ±0.2 (2Θ), 18.5 ±0.2 (2Θ), i 21.3 ±0.2 (2Θ); i/ili Ramanove vrpce kod 173 ±2 cm-1, 684 ±2 cm-1, 925 ±2 cm-1, 1298 ±2 cm-1, i 1464 ± 2 cm-1; ili
B: vrhove difrakcije X-zraka (CuKα zračenje) kod 17.5 ±0.2 (2Θ), 17.7 ±0.2 (2Θ) i 22.8 ±0.2 (2, i/ili Ramanove vrpce kod 175 ±2 cm-1, 686 ±2 cm-1, 928 ±2 cm-1, 1467 ±2 cm-1, i 2985 ± 2 cm-1; ili
C: Ramanove vrpce kod 156 ±2 cm-1, 1463 ±2 cm-1, 2927 ±2 cm-1, 2948 ±2 cm-1, 2951 ± 2 cm-1, 2971 ±2 cm-1, 3056 ± 2 cm-1 i 3068 ± 2 cm-1; ili
D: Ramanove vrpce kod 155 ±2 cm-1, 172 ±2 cm-1, 966 ±2 cm-1, 1310 ±2 cm-1, 2990 ± 2 cm-1, 3057 ±2 cm-1, i 3067 ± 2 cm-1; ili
E: vrhove difrakcije X-zraka (CuKα zračenje) kod 17.2 ±0.2 (2Θ), 19.5 ±0.2 (2Θ), i 20.3 ±0.2 (2Θ); ili
F: vrhove difrakcije X-zraka (CuKα zračenje) kod 10.2 ±0.2 (2Θ), 16.0 ±0.2 (2Θ), i 19.3 ±0.2 (2Θ); ili
G: vrhove difrakcije X-zraka (CuKα zračenje) kod 16.0 ±0.2 (2Θ), 17.9 ±0.2 (2Θ), i 18.8 ±0.2 (2Θ); ili
H: Ramanove vrpce kod 917 ±2 cm-1, 1003 ±2 cm-1, 1572 ±2 cm-1, 1586 ±2 cm-1, 162 ±2 cm-1, 175 ±2 cm-1, 1028 ±2 cm-1, i 1038 ±2 cm-1; ili
I: Ramanove vrpce kod 916 ±2 cm-1, 1003 ±2 cm-1, 1570 ±2 cm-1, 1582 ±2 cm-1, 169 ±2 cm-1, 368 ±2 cm-1, 397 ±2 cm-1, i 434 ±2 cm-1; ili
J: Ramanove vrpce kod 916 ±2 cm-1, 1003 ±2 cm-1, 1572 ±2 cm-1, 1585 ±2 cm-1 175 ±2 cm-1, 258 ±2 cm-1, 371 ±2 cm-1, i 441 ±2 cm-1 ili
K: Ramanove vrpce kod 918 ±2 cm-1, 1004 ±2 cm-1, 1568 ±2 cm-1, 1583 ±2 cm-1; 170 ±2 cm-1, 257 ±2 cm-1, 396 ±2 cm-1, i 489 ±2 cm-1.
7. Kristalni oblik prema zahtjevu 6, naznačen time da
A: kod DSC analize ispoljava višestruke endotermne događaje i egzotermni događaj s vrškom temperature u rasponu od 237-247 °C; ili
B: kod DSC analize ispoljava endotermni događaj s vrškom temperature u rasponu od 247-257 i egzotermni događaj s vrškom temperature u rasponu od 250-260 °C.
8. Farmaceutski pripravak naznačen time da sadrži barem jedan kruti oblik prema zahtjevu 1, 2 ili 3 ili barem jedan kristalni oblik prema bilo kojem od zahtjeva 4 do 7.
9. Farmaceutski pripravak prema zahtjevu 8 naznačen time da dodatno sadrži kruti oblik (1r,4r)-6'-fluoro-N,N-dimetil-4-fenil-4',9'-dihidro-3'H-spiro[ciklo-heksan-1,1'-pirano[3,4,b]indol]-4-amina (slobodna baza).
10. Postupak za dobivanje krutog oblika (1r,4r)-6'-fluoro-N,N-dimetil-4-fenil-4',9'-dihidro-3'H-spiro[cikloheksan-1,1'-pirano[3,4,b]indol]-4-amina i sumporne kiseline prema bilo kojem od zahtjeva 1 do 7, naznačen time da sadrži korake
(a-1) taloženje sulfata ili hemi-sulfata soli (1r,4r)-6'-fluoro-N,N-dimetil-4-fenil-4',9'-dihidro-3'H-spiro[cikloheksan-1,1'-pirano[3,4,b]indol]-4-amina iz otopine ili suspenzije slobodne baze; te
(b-1) odvajanje krutine; ili
(a-2) otapanje (1r,4r)-6'-fluoro-N,N-dimetil-4-fenil-4',9'-dihidro-3'H-spiro-[cikloheksan-1,1'-pirano[3,4,b]indol]-4-amin sulfata ili hemi-sulfata u otapalu; i
(b-2) isparavanje otapala iz otopine, ili
(b-2') taloženje (1r,4r)-6'-fluoro-N,N-dimetil-4-fenil-4',9'-dihidro-3'H-spiro-[cikloheksan-1,1'-pirano[3,4,b]indol]-4-amin sulfata ili hemi-sulfata iz otopine; ili
(a-3) suspendiranje (1r,4r)-6'-fluoro-N,N-dimetil-4-fenil-4',9'-dihidro-3'H-spiro-[cikloheksan-1,1'-pirano[3,4,b]indol]-4-amin sulfata ili hemi-sulfata u otapalu, te miješanje nastale suspenzije; i
(b-3) odvajanje krutine; ili
(a-4) reakciju 2-(5-fluoro-1H-indol-3-il)etanol i 4-(dimetilamino)-4-fenilcikloheksanona ili njegovog zaštićenog derivata, proizvoljno u obliku kisele adicijske soli, u ugljikovoj kiselini kao reakcijskom mediju u prisutnosti sumporne kiseline da nastane (1r,4r)-6'-fluoro-N,N-dimetil-4-fenil-4',9'-dihidro-3'H-spiro[cikloheksan-1,1'-pirano[3,4,b]indol]-4-amin sulfat ili hemi-sulfat; i
(b-4) odvajanje istaložene krutine;
(c-4) proizvoljno provođenje koraka (a-2) i (b-2) ili (b-2') ili provođenje koraka (a-3) i (b-3).
11. Kristalni oblik A (1r,4r)-6'-fluoro-N,N-dimetil-4-fenil-4',9'-dihidro-3'H-spiro-[cikloheksan-1,1'-pirano[3,4,b]indol]-4-amina i sumporne kiseline prema bilo kojem od zahtjeva 1-7 naznačen time da ima uzorak difrakcije X-zraka na prahu (CuKα zračenje) koji obuhvaća karakteristične vrhove kod 7.3 ±0.2 (2Θ), 9.2 ±0.2 (2Θ), 18.0 ±0.2 (2Θ), 18.5 ±0.2 (2Θ), 21.3 ±0.2 (2Θ), 25.6 ±0.2 (2Θ) i proizvoljno kod 14.6 ± 0.2 (2Θ) i 30.0 ±0.2 (2Θ).
12. Kristalni oblik B (1r,4r)-6'-fluoro-N,N-dimetil-4-fenil-4',9'-dihidro-3'H-spiro-[cikloheksan-1,1'-pirano[3,4,b]indol]-4-amina i sumporne kiseline prema bilo kojem od zahtjeva 1-7 naznačen time da ima uzorak difrakcije X-zraka na prahu (CuKα zračenje) koji obuhvaća karakteristične vrhove kod 10.2 ±0.2 (2Θ), 15.8 ±0.2 (2Θ), 17.5 ±0.2 (2Θ), 17.7 ±0.2 (2Θ), 18.4 ±0.2 (2Θ), 18.6 ±0.2 (2Θ), 22.8 ±0.2 (2Θ), 25.9 ±0.2 (2Θ), te proizvoljno kod 7.7 ± 0.2 (2Θ) i 23.1 ±0.2 (2Θ).
13. Kristalni oblik E (1r,4r)-6'-fluoro-N,N-dimetil-4-fenil-4',9'-dihidro-3'H-spiro-[cikloheksan-1,1'-pirano[3,4,b]indol]-4-amina i sumporne kiseline prema bilo kojem od zahtjeva 1-6 naznačen time da ima uzorak difrakcije X-zraka na prahu (CuKα zračenje) koji obuhvaća karakteristične vrhove kod 10.6 ±1.0 (2Θ), 15.9 ±1.0 (2Θ), 17.2 ±1.0 (2Θ), 19.5 ±1.0 (2Θ), 20.3 ±1.0 (2Θ), 22.1 ±1.0 (2Θ), i proizvoljno kod 13.7 ± 1.0 (2Θ) i 19.8 ±1.0 (2Θ).
14. Kristalni oblik F (1r,4r)-6'-fluoro-N,N-dimetil-4-fenil-4',9'-dihidro-3'H-spiro-[cikloheksan-1,1'-pirano[3,4,b]indol]-4-amina i sumporne kiseline prema bilo kojem od zahtjeva 1-6 naznačen time da ima uzorak difrakcije X-zraka na prahu (CuKα zračenje) koji obuhvaća karakteristične vrhove kod 10.2 ±1.0 (2Θ), 11.6 ±1.0 (2Θ), 16.0 ±1.0 (2Θ), 18.3 ±1.0 (2Θ), 19.3 ±1.0 (2Θ), i 24.5 ±1.0 (2Θ), te proizvoljno kod 12.4 ± 1.0 (2Θ) i 19.5 ±1.0 (2Θ).
15. Kristalni oblik G (1r,4r)-6'-fluoro-N,N-dimetil-4-fenil-4',9'-dihidro-3'H-spiro-[cikloheksan-1,1'-pirano[3,4,b]indol]-4-amina i sumporne kiseline prema bilo kojem od zahtjeva 1-6 naznačen time da ima uzorak difrakcije X-zraka na prahu (CuKα zračenje) koji obuhvaća karakteristične vrhove kod 10.3 ±1.0 (2Θ), 16.0 ±1.0 (2Θ), 17.9 ±1.0 (2Θ), 18.8 ±1.0 (2Θ), 23.0 ±1.0 (2Θ), i 26.2 ±1.0 (2Θ) i proizvoljno kod 14.6 ± 1.0 (2Θ) i 19.0 ±1.0 (2Θ).
16. Farmaceutski pripravak naznačen time da sadrži kristalni oblik prema bilo kojem od zahtjeva 11 do 15, koji poželjno sadrži između oko 0.001% težinski i oko 20% težinski kristalnog oblika.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11009774 | 2011-12-12 | ||
| PCT/EP2012/075004 WO2013087591A1 (en) | 2011-12-12 | 2012-12-11 | Solid forms of (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 and sulfuric acid |
| EP12798312.0A EP2797924B1 (en) | 2011-12-12 | 2012-12-11 | Solid forms of (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 and sulfuric acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20161105T1 true HRP20161105T1 (hr) | 2016-11-04 |
Family
ID=47324171
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20161105TT HRP20161105T1 (hr) | 2011-12-12 | 2016-08-30 | KRUTI OBLICI (1R,4R)-6'-FLUORO-N,N-DIMETIL-4-FENIL-4',9'-DIHIDRO-3'H-SPIRO[CIKLOHEKSAN-1,1'-PIRANO[3,4,b]INDOL]-4-AMINA I SUMPORNE KISELINE |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US8912343B2 (hr) |
| EP (1) | EP2797924B1 (hr) |
| JP (1) | JP6276703B2 (hr) |
| CN (1) | CN104114560B (hr) |
| AR (1) | AR089144A1 (hr) |
| AU (1) | AU2012350763B2 (hr) |
| BR (1) | BR112014014164A2 (hr) |
| CA (1) | CA2858769C (hr) |
| CY (1) | CY1117873T1 (hr) |
| DK (1) | DK2797924T3 (hr) |
| EA (1) | EA029975B1 (hr) |
| ES (1) | ES2589259T3 (hr) |
| HK (1) | HK1199256A1 (hr) |
| HR (1) | HRP20161105T1 (hr) |
| HU (1) | HUE029806T2 (hr) |
| IL (1) | IL233049A (hr) |
| MX (1) | MX354688B (hr) |
| PL (1) | PL2797924T3 (hr) |
| PT (1) | PT2797924T (hr) |
| RS (1) | RS54960B1 (hr) |
| SI (1) | SI2797924T1 (hr) |
| TW (1) | TWI567078B (hr) |
| WO (1) | WO2013087591A1 (hr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW201642853A (zh) | 2015-01-23 | 2016-12-16 | 歌林達有限公司 | 用於治療肝功能之損傷及／或腎功能之損傷個體疼痛之西博帕多（Ｃｅｂｒａｎｏｐａｄｏｌ） |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10252667A1 (de) * | 2002-11-11 | 2004-05-27 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
| DE102006046745A1 (de) | 2006-09-29 | 2008-04-03 | Grünenthal GmbH | Gemischte ORL1/µ-Agonisten zur Behandlung von Schmerz |
| BR112013002696A2 (pt) * | 2010-08-04 | 2016-05-31 | Gruenenthal Gmbh | forma de dosagem farmacêutica compreendendo 6'-fluor-(n-metil- ou n,n-dimetil-)4-fenil-4',9'-diidro-3'h-espiro[cicloexano-1,-1'-pirano[3,4-b]indol]-4 amina 13'' |
| WO2012016703A2 (en) * | 2010-08-04 | 2012-02-09 | 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 |
-
2012
- 2012-12-11 SI SI201230647A patent/SI2797924T1/sl unknown
- 2012-12-11 EP EP12798312.0A patent/EP2797924B1/en active Active
- 2012-12-11 CA CA2858769A patent/CA2858769C/en active Active
- 2012-12-11 ES ES12798312.0T patent/ES2589259T3/es active Active
- 2012-12-11 HU HUE12798312A patent/HUE029806T2/hu unknown
- 2012-12-11 EA EA201400684A patent/EA029975B1/ru not_active IP Right Cessation
- 2012-12-11 CN CN201280060988.XA patent/CN104114560B/zh not_active Expired - Fee Related
- 2012-12-11 US US13/711,375 patent/US8912343B2/en active Active
- 2012-12-11 PT PT127983120T patent/PT2797924T/pt unknown
- 2012-12-11 RS RS20160635A patent/RS54960B1/sr unknown
- 2012-12-11 JP JP2014546452A patent/JP6276703B2/ja active Active
- 2012-12-11 TW TW101146482A patent/TWI567078B/zh not_active IP Right Cessation
- 2012-12-11 BR BR112014014164A patent/BR112014014164A2/pt not_active IP Right Cessation
- 2012-12-11 DK DK12798312.0T patent/DK2797924T3/en active
- 2012-12-11 MX MX2014007012A patent/MX354688B/es active IP Right Grant
- 2012-12-11 AR ARP120104641A patent/AR089144A1/es unknown
- 2012-12-11 PL PL12798312.0T patent/PL2797924T3/pl unknown
- 2012-12-11 WO PCT/EP2012/075004 patent/WO2013087591A1/en active Application Filing
- 2012-12-11 AU AU2012350763A patent/AU2012350763B2/en not_active Ceased
-
2014
- 2014-06-10 IL IL233049A patent/IL233049A/en active IP Right Grant
- 2014-12-23 HK HK14112856.2A patent/HK1199256A1/zh not_active IP Right Cessation
-
2016
- 2016-08-03 CY CY20161100764T patent/CY1117873T1/el unknown
- 2016-08-30 HR HRP20161105TT patent/HRP20161105T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2858769C (en) | 2017-10-24 |
| IL233049A (en) | 2017-09-28 |
| MX2014007012A (es) | 2014-07-14 |
| CY1117873T1 (el) | 2017-05-17 |
| HK1199256A1 (zh) | 2015-06-26 |
| PL2797924T3 (pl) | 2016-10-31 |
| TW201329081A (zh) | 2013-07-16 |
| EP2797924A1 (en) | 2014-11-05 |
| US20130150589A1 (en) | 2013-06-13 |
| EA029975B1 (ru) | 2018-06-29 |
| CN104114560B (zh) | 2018-05-04 |
| RS54960B1 (sr) | 2016-11-30 |
| HUE029806T2 (hu) | 2017-03-28 |
| EA201400684A1 (ru) | 2014-12-30 |
| IL233049A0 (en) | 2014-07-31 |
| JP2015500311A (ja) | 2015-01-05 |
| TWI567078B (zh) | 2017-01-21 |
| BR112014014164A2 (pt) | 2017-06-13 |
| AR089144A1 (es) | 2014-07-30 |
| DK2797924T3 (en) | 2016-08-01 |
| SI2797924T1 (sl) | 2016-08-31 |
| WO2013087591A1 (en) | 2013-06-20 |
| MX354688B (es) | 2018-03-15 |
| ES2589259T3 (es) | 2016-11-11 |
| JP6276703B2 (ja) | 2018-02-07 |
| AU2012350763B2 (en) | 2017-03-30 |
| PT2797924T (pt) | 2016-09-08 |
| US8912343B2 (en) | 2014-12-16 |
| CN104114560A (zh) | 2014-10-22 |
| AU2012350763A1 (en) | 2014-07-31 |
| EP2797924B1 (en) | 2016-06-01 |
| CA2858769A1 (en) | 2013-06-20 |
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