HRP20170481T1 - Kristalne modifikacije (1r, 2r)-3-(3-dimentil amino-1-etil-2-metil-propil) fenola - Google Patents
Kristalne modifikacije (1r, 2r)-3-(3-dimentil amino-1-etil-2-metil-propil) fenola Download PDFInfo
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- HRP20170481T1 HRP20170481T1 HRP20170481TT HRP20170481T HRP20170481T1 HR P20170481 T1 HRP20170481 T1 HR P20170481T1 HR P20170481T T HRP20170481T T HR P20170481TT HR P20170481 T HRP20170481 T HR P20170481T HR P20170481 T1 HRP20170481 T1 HR P20170481T1
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- Prior art keywords
- ethyl
- ray diffraction
- crystal modification
- phenol
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- 238000012986 modification Methods 0.000 title claims 20
- 230000004048 modification Effects 0.000 title claims 20
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title 1
- 239000013078 crystal Substances 0.000 claims 15
- 238000002441 X-ray diffraction Methods 0.000 claims 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 12
- KWTWDQCKEHXFFR-SMDDNHRTSA-N tapentadol Chemical compound CN(C)C[C@H](C)[C@@H](CC)C1=CC=CC(O)=C1 KWTWDQCKEHXFFR-SMDDNHRTSA-N 0.000 claims 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 9
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 9
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 6
- 239000000725 suspension Substances 0.000 claims 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- 239000002552 dosage form Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 230000008020 evaporation Effects 0.000 claims 1
- 238000001704 evaporation Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 238000002156 mixing Methods 0.000 claims 1
- 238000001556 precipitation Methods 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C215/48—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups
- C07C215/54—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that 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]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Rheumatology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Claims (18)
1. Kristalna modifikacija A (1R,2R)-3-(3-dimetilamino-1-etil-2-metilpropil)fenola naznačena time da sadrži odraz difrakcije X-zraka kod 15.58±0.20 (2Θ), te pored toga barem jedan odraz difrakcije X-zraka koji je odabran iz skupine koju čine 28.37±0.20 (2Θ) i 34.45±0.20 (2Θ) i dodatno barem jedan odraz difrakcije X-zraka koji je odabran iz skupine koju čine 13.71±0.20 (2Θ), 14.80±0.20 (2Θ), 16.89±0.20 (2Θ), 17.79±0.20 (2Θ), 18.45±0.20 (2Θ), 20.20±0.20 (2Θ), 20.92±0.20 (2Θ), 22.50±0.20 (2Θ), 24.37±0.20 (2Θ) i 25.33±0.20 (2Θ).
2. Kristalna modifikacija A prema zahtjevu 1, naznačena time da sadrži pored toga barem jedan odraz difrakcije X-zraka koji je odabran iz skupine koju čine 14.11+0.20 (2Θ), 19.07±0.20 (2Θ), 21.12±0.20 (2Θ), 21.90±0.20 (2Θ), 22.21±0.20 (2Θ), 24.75+0.20 (2Θ), 27.32±0.20 (2Θ), 27.55±0.20 (2Θ), 29.90±0.20 (2Θ) i 30.68±0.20 (2Θ).
3. Kristalna modifikacija A prema bilo kojem od zahtjeva 1 i 2, naznačena time da ne sadrži barem jedan odraz difrakcije X-zraka koji je odabran iz skupine koju čine 8.10±0.20 (2Θ), 10.93+0.20 (2Θ) 11.83+0.20 (2Θ), 12.41±0.20 (2Θ), 26.22±0.20 (2Θ), 26.54±0.20 (2Θ) i 26.72±0.20 (2Θ).
4. Kristalna modifikacija A prema bilo kojem od zahtjeva 1-3, naznačena time da ima endotermu u rasponu od 75 do 84°C kod DSC.
5. Postupak za pripremanje kristalne modifikacije A prema bilo kojem od zahtjeva 1-4 naznačen time da sadrži korake
(a) koncentriranje otopine (1R,2R)-3-(3-dimetilamino-1-etil-2-metilpropil)fenola, pri čemu je otapalo metanol, etanol, 1-propanol, 2-propanol, etil acetat, aceton, etil metil keton, dietil eter, tert-butil metil eter, 1,4-dioksan, tetrahidrofuran, acetonitril, diklorometan, toluen, dimetilformamid ili dimetil sulfoksid, i
(b) pohranjivanje ostatka dobivenog u koraku (a) kod temperature od > 5°C.
6. Kristalna modifikacija B (1R,2R)-3-(3-dimetilamino-1-etil-2-metilpropil)fenola naznačena time da obuhvaća odraz difrakcije X-zraka kod 29.06+0.20 (2Θ), te pored toga barem jedan odraz difrakcije X-zraka koji je odabran iz skupine koju čine 19.50±0.20 (2Θ), 35.49±0.20 (2Θ) i 40.01±0.20 (2Θ) i pored toga barem jedan odraz difrakcije X-zraka koji je odabran iz skupine koju čine 14.11±0.20 (2Θ), 14.44±0.20 (2Θ), 16.08±0.20 (2Θ), 17.17±0.20 (2Θ), 17.43±0.20 (2Θ), 18.81±0.20 (2Θ), 20.24±0.20 (2Θ), 20.80±0.20 (2Θ), 22.00±0.20 (2Θ), 22.49±0.20 (2Θ), 23.40±0.20 (2Θ), 24.15±0.20 (2Θ), 24.51±0.20 (2Θ) i 29.89±0.20 (2Θ).
7. Kristalna modifikacija B prema zahtjevu 6, naznačena time da sadrži dodatno barem jedan odraz difrakcije X-zraka koji je odabran iz skupine koju čine 18.67+0.20 (2Θ), 25.24±0.20 (2Θ), 25.36±0.20 (2Θ), 27.58+0.20 (2Θ), 27.79±0.20 (2Θ), 30.11±0.20 (2Θ) i 31.00±0.20 (2Θ).
8. Kristalna modifikacija B prema bilo kojem od zahtjeva 6 i 7, naznačena time da ne sadrži najmanje jedan odraz difrakcije X-zraka koji je odabran iz skupine koju čine 8.10+0.20 (2Θ), 10.93±0.20 (2Θ), 11.83±0.20 (2Θ), 12.41+0.20 (2Θ), 26.22±0.20 (2Θ), 26.54±0.20 (2Θ) i 26.72±0.20 (2Θ).
9. Kristalna modifikacija B prema bilo kojem od zahtjeva 6-8, naznačena time da ima endotermu u rasponu od 87 do 93°C kod DSC.
10. Postupak za pripremanje kristalne modifikacije B prema bilo kojem od zahtjeva 6-8 naznačen time da sadrži korake
(a) koncentriranje otopine (1R,2R)-3-(3-dimetilamino-1-etil-2-metilpropil)fenola, pri čemu je otapalo metanol, etanol, 1-propanol, 2-propanol, etil acetat, aceton, etil metil keton, dietil eter, tert-butil metil eter, 1,4-dioksan, tetrahidrofuran, acetonitril, diklorometan, toluen, dimetilformamid ili dimetil sulfoksid, te
(b1) pohranjivanje ostatka dobivenog u koraku (a) kod temperature od ≤ 5°C, ili
(b2) suspendiranje ostatka dobivenog u skladu s korakom (a) i miješanje ove suspenzije.
11. Postupak za pripremanje kristalne modifikacije B prema bilo kojem od zahtjeva 6-8 naznačen time da sadrži korak
(a) taloženja (1R,2R)-3-(3-dimetilamino-1-etil-2-metilpropil)fenola iz otopine, pri čemu je otapalo metanol, etanol, 1-propanol, 2-propanol, etil acetat, aceton, etil metil keton, dietil eter, tert-butil metil eter, 1,4-dioksan, tetrahidrofuran, acetonitril, diklorometan, toluen, dimetilformamid ili dimetil sulfoksid.
12. Kristalna modifikacija C (1R,2R)-3-(3-dimetilamino-1-etil-2-metilpropil)fenola naznačena time da sadrži barem jedan odraz difrakcije X-zraka koji je odabran iz skupine koju čine 10.93±0.20 (2Θ), 12.41±0.20 (2Θ) i 26.22±0.20 (2Θ), te pored toga barem jedan odraz difrakcije X-zraka koji je odabran iz skupine koju čine 8.10±0.20 (2Θ), 11.83±0.20 (2Θ), 26.54±0.20 (2Θ) i 26.72±0.20 (2Θ) i pored toga barem jedan odraz difrakcije X-zraka koji je odabran iz skupine koju čine 13.71±0.20 (2Θ), 14.13+0.20 (2Θ), 14.82±0.20 (2Θ), 15.34±0.20 (2Θ), 15.59±0.20 (2Θ), 16.10±0.20 (2Θ), 16.43±0.20 (2Θ), 16.91±0.20 (2Θ), 17.32±0.20 (2Θ), 17.58±0.20 (2Θ), 17.82±0.20 (2Θ), 18.01±0.20 (2Θ), 18.46±0.20 (2Θ), 19.05±0.20 (2Θ), 20.23+0.20 (2Θ), 20.71+0.20 (2Θ), 20.94+0.20 (2Θ), 21.17+0.20 (2Θ), 21.90±0.20 (2Θ), 22.23±0.20 (2Θ), 22.52±0.20 (2Θ), 23.32±0.20 (2Θ), 24.12±0.20 (2Θ), 24.39±0.20 (2Θ), 24.92±0.20 (2Θ), 25.35±0.20 (2Θ), 27.33±0.20 (2Θ), 27.63±0.20 (2Θ), 27.84±0.20 (2Θ), 28.48±0.20 (2Θ), 29.64±0.20 (2Θ), 29.94±0.20 (2Θ), 30.54±0.20 (2Θ), 30.68±0.20 (2Θ), 31.03±0.20 (2Θ), 31.52±0.20 (2Θ), 32.29±0.20 (2Θ), 32.93±0.20 (2Θ), 33.66±0.20 (2Θ), 35.52±0.20 (2Θ), 36.05±0.20 (2Θ), 36.64±0.20 (2Θ), 37.54±0.20 (2Θ), 38.45±0.20 (2Θ), 39.15±0.20 (2Θ) i 40.05±0.20 (2Θ).
13. Kristalna modifikacija C prema zahtjevu 12, naznačena time da ima endotermu s vrškom temperature kod 75-84°C i/ili endotermu s vrškom temperature kod 87-93°C kod DSC ispitivanja.
14. Postupak za pripremanje kristalne modifikacije C prema bilo kojem od zahtjeva 12 i 13 naznačen time da sadrži korake
(a) protresanje suspenzije koja sadrži kristalnu modifikaciju A i/ili kristalnu modifikaciju B (1R,2R)-3-(3-dimetilamino-1-etil-2-metilpropil)fenola, pri čemu je suspenzijski medij metanol ili toluen,
i
(b) isparavanje suspenzijskog medija u struji zraka.
15. Farmaceutski pripravak naznačen time da sadrži kristalnu modifikaciju (1R,2R)-3-(3-dimetilamino-1-etil-2-metilpropil)fenola prema jednom ili više od zahtjeva 1-4, 6-9 i 12-13 i farmaceutski kompatibilni nosač.
16. Farmaceutski oblik doziranja naznačen time da sadrži farmaceutski pripravak prema zahtjevu 15.
17. Kristalna modifikacija (1R,2R)-3-(3-dimetilamino-1-etil-2-metilpropil)fenola prema jednom ili više od zahtjeva 1-4, 6-9 i 12-13 naznačena time da se koristi kao lijek.
18. Kristalna modifikacija (1R,2R)-3-(3-dimetilamino-1-etil-2-metilpropil)fenola prema jednom ili više od zahtjeva 1-4, 6-9 i 12-13 naznačena time da je za uporabu za borbu protiv boli.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07023728 | 2007-12-07 | ||
| EP08857298.7A EP2240431B1 (de) | 2007-12-07 | 2008-12-05 | Kristalline modifikationen von (1r,2r)-3-(3-dimethylamino-1-ethyl-2-methyl-propyl)-phenol |
| PCT/EP2008/010330 WO2009071310A1 (de) | 2007-12-07 | 2008-12-05 | Kristalline modifikationen von (1r,2r)-3-(3-dimethylamino-1-ethyl-2-methyl-propyl)-phenol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20170481T1 true HRP20170481T1 (hr) | 2017-05-19 |
Family
ID=39272207
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20170481TT HRP20170481T1 (hr) | 2007-12-07 | 2017-03-21 | Kristalne modifikacije (1r, 2r)-3-(3-dimentil amino-1-etil-2-metil-propil) fenola |
| HRP20200067TT HRP20200067T1 (hr) | 2007-12-07 | 2020-01-16 | Medikamenti koji sadrže kristalne modifikacije (1r,2r)-3-(3-dimetilamino-1-etil-2-metilpropil)fenola |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20200067TT HRP20200067T1 (hr) | 2007-12-07 | 2020-01-16 | Medikamenti koji sadrže kristalne modifikacije (1r,2r)-3-(3-dimetilamino-1-etil-2-metilpropil)fenola |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US8134032B2 (hr) |
| EP (2) | EP2240431B1 (hr) |
| CN (3) | CN101939287B (hr) |
| CY (2) | CY1118976T1 (hr) |
| DK (2) | DK3173400T3 (hr) |
| ES (2) | ES2764451T3 (hr) |
| HR (2) | HRP20170481T1 (hr) |
| HU (2) | HUE047275T2 (hr) |
| IL (2) | IL206197A (hr) |
| LT (1) | LT2240431T (hr) |
| PL (2) | PL2240431T3 (hr) |
| PT (2) | PT3173400T (hr) |
| SI (2) | SI2240431T1 (hr) |
| WO (1) | WO2009071310A1 (hr) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100272815A1 (en) * | 2009-04-28 | 2010-10-28 | Actavis Group Ptc Ehf | Amorphous form of tapentadol hydrochloride |
| US8288592B2 (en) | 2009-09-22 | 2012-10-16 | Actavis Group Ptc Ehf | Solid state forms of tapentadol salts |
| EP2566461A2 (de) | 2010-05-05 | 2013-03-13 | Ratiopharm GmbH | Festes tapentadol in nicht-kristalliner form |
| WO2012051246A1 (en) | 2010-10-12 | 2012-04-19 | Ratiopharm Gmbh | Tapentadol hydrobromide and crystalline forms thereof |
| WO2013111161A2 (en) * | 2012-01-10 | 2013-08-01 | Msn Laboratories Limited | Process for the preparation of 3-aryl-2-methyl-propanamine derivatives and polymorphs thereof |
| WO2014023652A1 (en) * | 2012-08-06 | 2014-02-13 | Ratiopharm Gmbh | Pharmaceutical formulation comprising tapentadol and cyclodextrin |
| EP2808319A1 (en) | 2013-05-31 | 2014-12-03 | Arevipharma GmbH | 3-[3-(Dimethylamino)-1-ethyl-2-methylpropyl]phenol resin complex |
| CZ307492B6 (cs) | 2014-02-04 | 2018-10-17 | Zentiva, K.S. | Pevná forma maleátu tapentadolu a způsob její přípravy |
| GB2523089A (en) * | 2014-02-12 | 2015-08-19 | Azad Pharmaceutical Ingredients Ag | Stable polymorph form B of tapentadol hydrochloride |
| ES2966219T3 (es) | 2016-04-19 | 2024-04-19 | Ratiopharm Gmbh | Fosfato de tapentadol amorfo |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1027666C (zh) * | 1993-02-20 | 1995-02-15 | 袁晓辉 | 高分子聚合物正温度系数热敏电阻材料 |
| DE4426245A1 (de) * | 1994-07-23 | 1996-02-22 | Gruenenthal Gmbh | 1-Phenyl-3-dimethylamino-propanverbindungen mit pharmakologischer Wirkung |
| PE20030527A1 (es) * | 2001-10-24 | 2003-07-26 | Gruenenthal Chemie | Formulacion farmaceutica con liberacion retardada que contiene 3-(3-dimetilamino-1-etil-2-metil-propil) fenol o una sal farmaceuticamente aceptable del mismo y tabletas para administracion oral que la contienen |
| DE10326097A1 (de) * | 2003-06-06 | 2005-01-05 | Grünenthal GmbH | Verfahren zur Herstellung von Dimethyl-(3-aryl-butyl)-aminverbindungen |
| ATE368639T1 (de) * | 2004-06-28 | 2007-08-15 | Gruenenthal Gmbh | Kristalline formen von (-)-(1r,2r)-3-(3- dimethylamino-1-ethyl-2-methylpropyl)-phenol hydrochlorid |
| DE102005034974A1 (de) * | 2005-07-22 | 2007-04-19 | Grünenthal GmbH | Salz von Dimethylaminomethyl-phenyl-cyclohexan und dessen kristalline Formen |
| US20070254960A1 (en) * | 2006-04-28 | 2007-11-01 | Gruenenthal Gmbh | Pharmaceutical combination |
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2008
- 2008-12-05 HU HUE16203848A patent/HUE047275T2/hu unknown
- 2008-12-05 DK DK16203848T patent/DK3173400T3/da active
- 2008-12-05 US US12/329,111 patent/US8134032B2/en active Active
- 2008-12-05 ES ES16203848T patent/ES2764451T3/es active Active
- 2008-12-05 DK DK08857298.7T patent/DK2240431T3/en active
- 2008-12-05 SI SI200831791A patent/SI2240431T1/sl unknown
- 2008-12-05 LT LTEP08857298.7T patent/LT2240431T/lt unknown
- 2008-12-05 PT PT162038483T patent/PT3173400T/pt unknown
- 2008-12-05 ES ES08857298.7T patent/ES2623413T3/es active Active
- 2008-12-05 EP EP08857298.7A patent/EP2240431B1/de active Active
- 2008-12-05 PT PT88572987T patent/PT2240431T/pt unknown
- 2008-12-05 PL PL08857298T patent/PL2240431T3/pl unknown
- 2008-12-05 PL PL16203848T patent/PL3173400T3/pl unknown
- 2008-12-05 CN CN200880126383.XA patent/CN101939287B/zh active Active
- 2008-12-05 WO PCT/EP2008/010330 patent/WO2009071310A1/de active Application Filing
- 2008-12-05 HU HUE08857298A patent/HUE031126T2/en unknown
- 2008-12-05 SI SI200832101T patent/SI3173400T1/sl unknown
- 2008-12-05 EP EP16203848.3A patent/EP3173400B1/de active Active
- 2008-12-05 CN CN201410468681.4A patent/CN104447361B/zh active Active
- 2008-12-05 CN CN201410468436.3A patent/CN104447360B/zh active Active
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2010
- 2010-06-06 IL IL206197A patent/IL206197A/en active IP Right Grant
-
2015
- 2015-03-01 IL IL237478A patent/IL237478A0/en unknown
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2017
- 2017-03-21 HR HRP20170481TT patent/HRP20170481T1/hr unknown
- 2017-04-07 CY CY20171100414T patent/CY1118976T1/el unknown
-
2019
- 2019-12-04 CY CY20191101278T patent/CY1122416T1/el unknown
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Also Published As
| Publication number | Publication date |
|---|---|
| DK2240431T3 (en) | 2017-04-10 |
| EP3173400A1 (de) | 2017-05-31 |
| CN104447360B (zh) | 2017-04-12 |
| CN101939287A (zh) | 2011-01-05 |
| EP3173400B1 (de) | 2019-11-06 |
| CY1118976T1 (el) | 2018-01-10 |
| HUE031126T2 (en) | 2017-07-28 |
| PL2240431T3 (pl) | 2017-07-31 |
| CN104447360A (zh) | 2015-03-25 |
| EP2240431B1 (de) | 2017-01-25 |
| IL206197A0 (en) | 2010-12-30 |
| HUE047275T2 (hu) | 2020-04-28 |
| PL3173400T3 (pl) | 2020-05-18 |
| ES2764451T3 (es) | 2020-06-03 |
| LT2240431T (lt) | 2017-04-10 |
| SI3173400T1 (sl) | 2020-01-31 |
| EP2240431A1 (de) | 2010-10-20 |
| WO2009071310A1 (de) | 2009-06-11 |
| IL237478A0 (en) | 2015-04-30 |
| CN104447361A (zh) | 2015-03-25 |
| CY1122416T1 (el) | 2021-01-27 |
| PT3173400T (pt) | 2019-12-13 |
| CN104447361B (zh) | 2017-04-12 |
| ES2623413T3 (es) | 2017-07-11 |
| US20090149534A1 (en) | 2009-06-11 |
| CN101939287B (zh) | 2014-10-22 |
| IL206197A (en) | 2015-03-31 |
| SI2240431T1 (sl) | 2017-05-31 |
| HRP20200067T1 (hr) | 2020-04-03 |
| US8134032B2 (en) | 2012-03-13 |
| DK3173400T3 (da) | 2019-11-25 |
| PT2240431T (pt) | 2017-05-03 |
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