JP2006528604A - ６−ジメチルアミノメチル−１−（３−メトキシ−フェニル）−シクロヘキサン−１，３−ジオールを含む、有効物質徐放性医薬 - Google Patents
６−ジメチルアミノメチル−１−（３−メトキシ−フェニル）−シクロヘキサン−１，３−ジオールを含む、有効物質徐放性医薬 Download PDFInfo
- Publication number
- JP2006528604A JP2006528604A JP2006520768A JP2006520768A JP2006528604A JP 2006528604 A JP2006528604 A JP 2006528604A JP 2006520768 A JP2006520768 A JP 2006520768A JP 2006520768 A JP2006520768 A JP 2006520768A JP 2006528604 A JP2006528604 A JP 2006528604A
- Authority
- JP
- Japan
- Prior art keywords
- weight
- methoxy
- diol
- cyclohexane
- dimethylaminomethyl
- 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.)
- Pending
Links
- LQJLLAOISDVBJM-UHFFFAOYSA-N 6-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexane-1,3-diol Chemical compound COC1=CC=CC(C2(O)C(CCC(O)C2)CN(C)C)=C1 LQJLLAOISDVBJM-UHFFFAOYSA-N 0.000 title claims abstract description 73
- 239000013543 active substance Substances 0.000 title claims abstract description 71
- 239000012730 sustained-release form Substances 0.000 title claims abstract description 47
- 238000013268 sustained release Methods 0.000 title claims abstract description 46
- 239000011159 matrix material Substances 0.000 claims abstract description 42
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 33
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 31
- 150000003839 salts Chemical class 0.000 claims abstract description 22
- 238000000034 method Methods 0.000 claims abstract description 15
- 229920001600 hydrophobic polymer Polymers 0.000 claims abstract description 10
- 229920001477 hydrophilic polymer Polymers 0.000 claims abstract description 9
- 238000000338 in vitro Methods 0.000 claims abstract description 7
- 239000000825 pharmaceutical preparation Substances 0.000 claims abstract description 6
- 238000001514 detection method Methods 0.000 claims abstract description 5
- 238000000870 ultraviolet spectroscopy Methods 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 44
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 15
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 15
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 11
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 claims description 11
- 239000007864 aqueous solution Substances 0.000 claims description 8
- 229920002678 cellulose Polymers 0.000 claims description 8
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- 239000001856 Ethyl cellulose Substances 0.000 claims description 3
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 claims description 3
- 229920001249 ethyl cellulose Polymers 0.000 claims description 3
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 239000000463 material Substances 0.000 description 4
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- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- 229920002988 biodegradable polymer Polymers 0.000 description 2
- 239000004621 biodegradable polymer Substances 0.000 description 2
- FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 2
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- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
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- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920000193 polymethacrylate Polymers 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
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- 238000003860 storage Methods 0.000 description 2
- 239000001797 sucrose acetate isobutyrate Substances 0.000 description 2
- 235000010983 sucrose acetate isobutyrate Nutrition 0.000 description 2
- UVGUPMLLGBCFEJ-SWTLDUCYSA-N sucrose acetate isobutyrate Chemical compound CC(C)C(=O)O[C@H]1[C@H](OC(=O)C(C)C)[C@@H](COC(=O)C(C)C)O[C@@]1(COC(C)=O)O[C@@H]1[C@H](OC(=O)C(C)C)[C@@H](OC(=O)C(C)C)[C@H](OC(=O)C(C)C)[C@@H](COC(C)=O)O1 UVGUPMLLGBCFEJ-SWTLDUCYSA-N 0.000 description 2
- 230000002459 sustained effect Effects 0.000 description 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- XBBVURRQGJPTHH-UHFFFAOYSA-N 2-hydroxyacetic acid;2-hydroxypropanoic acid Chemical compound OCC(O)=O.CC(O)C(O)=O XBBVURRQGJPTHH-UHFFFAOYSA-N 0.000 description 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- WSVLPVUVIUVCRA-KPKNDVKVSA-N Alpha-lactose monohydrate Chemical compound O.O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O WSVLPVUVIUVCRA-KPKNDVKVSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 208000000094 Chronic Pain Diseases 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 229920003134 Eudragit® polymer Polymers 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000036592 analgesia Effects 0.000 description 1
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- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
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- 150000003840 hydrochlorides Chemical class 0.000 description 1
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- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
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- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
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- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- ULIAPOFMBCCSPE-UHFFFAOYSA-N tridecan-7-one Chemical compound CCCCCCC(=O)CCCCCC ULIAPOFMBCCSPE-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
-
- 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]
Landscapes
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Pain & Pain Management (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10333835A DE10333835A1 (de) | 2003-07-24 | 2003-07-24 | 6-Dimethylaminomethyl-1-(3-methoxy-phenyl)-cyclohexane-1,3-diol enthaltendes Arzneimittel mit verzögerter Wirkstofffreisetzung |
| PCT/EP2004/008081 WO2005009329A2 (de) | 2003-07-24 | 2004-07-20 | 6-dimethylaminomethyl-1-(3-methoxy-phenyl)-cyclohexane-1,3-diol enthaltendes arzneimittel mit verzögerter wirkstofffreisetzung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006528604A true JP2006528604A (ja) | 2006-12-21 |
| JP2006528604A5 JP2006528604A5 (enExample) | 2011-11-17 |
Family
ID=34088810
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006520768A Pending JP2006528604A (ja) | 2003-07-24 | 2004-07-20 | ６−ジメチルアミノメチル−１−（３−メトキシ−フェニル）−シクロヘキサン−１，３−ジオールを含む、有効物質徐放性医薬 |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US20060121113A1 (enExample) |
| EP (1) | EP1648420A2 (enExample) |
| JP (1) | JP2006528604A (enExample) |
| CA (1) | CA2533330A1 (enExample) |
| DE (1) | DE10333835A1 (enExample) |
| WO (1) | WO2005009329A2 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX2007010192A (es) * | 2005-02-25 | 2007-09-07 | Gruenenthal Chemie | Formas cristalinas del clorhidrato de (1rs, 3rs, 6rs)-6-dimetilaminometil-1-(3-metoxi-fenil) ciclohexano-1, 3-diol. |
| DE102005009217A1 (de) * | 2005-02-25 | 2006-08-31 | Grünenthal GmbH | Phosphatsalze der 6-Dimethylaminomethyl-1-(3-methoxyphenyl)-1,3-dihydroxy-cyclohexanverbindungen |
| EP1695957A1 (en) * | 2005-02-25 | 2006-08-30 | Grünenthal GmbH | Crystalline forms of (1RS,3RS,6RS)-6-Dimethylaminomethyl-1-(3-methoxy-phenyl)cyclohexane-1,3-diol hydrochloride |
| US20090104266A1 (en) * | 2005-09-15 | 2009-04-23 | Tobias Jung | 3-(2-dimethylaminomethylcy clohexyl)phenol retard formulation |
| AU2007234612B2 (en) * | 2006-12-14 | 2013-06-27 | Johnson & Johnson Regenerative Therapeutics, Llc | Protein stabilization formulations |
| DE102007022790A1 (de) * | 2007-05-11 | 2008-11-20 | Grünenthal GmbH | Axomadol zur Schmerzbehandlung bei Arthrose |
| US7678764B2 (en) | 2007-06-29 | 2010-03-16 | Johnson & Johnson Regenerative Therapeutics, Llc | Protein formulations for use at elevated temperatures |
| JP5323832B2 (ja) | 2007-08-07 | 2013-10-23 | アドバンスト・テクノロジーズ・アンド・リジェネレイティブ・メディスン・エルエルシー | 酸性水溶液中にｇｄｆ−５を含むタンパク質製剤 |
| EP2085081A1 (de) * | 2008-02-04 | 2009-08-05 | Grünenthal GmbH | 3-(2-Dimethylaminomethyl-cyclohexyl)-phenol gegen polyneuropathischen Schmerz |
| BRPI0911048A2 (pt) * | 2008-04-14 | 2015-12-29 | Atrm Llc | formulações líquidas tamponadas de gdf-5 |
| DE102008042603A1 (de) * | 2008-10-06 | 2010-04-08 | Biotronik Vi Patent Ag | Implantat sowie Verfahren zur Herstellung einer degradationshemmenden Schicht auf einer Körperoberfläche eines Implantats |
| WO2011008298A2 (en) * | 2009-07-16 | 2011-01-20 | Nectid, Inc. | Novel axomadol dosage forms |
| US20110053914A1 (en) | 2009-08-28 | 2011-03-03 | Gruenenthal Gmbh | Pharmaceutical Combination Comprising 6-Dimethylaminomethyl-1-(3-methoxy-phenyl)-cyclohexane-1,3-diol or 6-Dimethylaminomethyl-1-(3-hydroxy-phenyl)-cyclohexane-1,3-diol and an Antiepileptic |
| EP2477960A1 (en) | 2009-09-14 | 2012-07-25 | Grünenthal GmbH | Crystalline modifications of 6-dimethylaminomethyl-1-(3-methoxy-phenyl)-cyclohexane-1,3-diol |
| US20120022294A1 (en) | 2010-06-30 | 2012-01-26 | Gruenenthal Gmbh | Axomadol or a Metabolite Thereof for Use in the Treatment of Irritable Bowel Syndrome |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002043714A2 (de) * | 2000-11-30 | 2002-06-06 | Grünenthal GmbH | Verwendung von substituierten 6-dimethylaminomethyl-1-phenyl-cyclohexanverbindungen zur therapie der harninkontinenz |
| WO2002067916A2 (de) * | 2001-02-28 | 2002-09-06 | Grünenthal GmbH | Pharmazeutische salze |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3810343A1 (de) * | 1988-03-26 | 1989-10-05 | Basf Ag | Verfahren zur herstellung von festen pharmazeutischen retardformen |
| DE4315525B4 (de) * | 1993-05-10 | 2010-04-15 | Euro-Celtique S.A. | Pharmazeutische Zusammensetzung |
| DE4329794C2 (de) * | 1993-09-03 | 1997-09-18 | Gruenenthal Gmbh | Tramadolsalz enthaltende Arzneimittel mit verzögerter Wirkstofffreisetzung |
| DE19525137C2 (de) * | 1995-07-11 | 2003-02-27 | Gruenenthal Gmbh | 6-Dimethylaminomethyl-1-phenyl-cyclohexanverbin -dungen als Zwischenprodukte zur Herstellung pharmazeutischer Wirkstoffe |
-
2003
- 2003-07-24 DE DE10333835A patent/DE10333835A1/de not_active Ceased
-
2004
- 2004-07-20 CA CA002533330A patent/CA2533330A1/en not_active Abandoned
- 2004-07-20 JP JP2006520768A patent/JP2006528604A/ja active Pending
- 2004-07-20 WO PCT/EP2004/008081 patent/WO2005009329A2/de not_active Ceased
- 2004-07-20 EP EP04741158A patent/EP1648420A2/de not_active Withdrawn
-
2006
- 2006-01-19 US US11/334,344 patent/US20060121113A1/en not_active Abandoned
-
2010
- 2010-04-09 US US12/757,455 patent/US20100196473A1/en not_active Abandoned
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002043714A2 (de) * | 2000-11-30 | 2002-06-06 | Grünenthal GmbH | Verwendung von substituierten 6-dimethylaminomethyl-1-phenyl-cyclohexanverbindungen zur therapie der harninkontinenz |
| WO2002067916A2 (de) * | 2001-02-28 | 2002-09-06 | Grünenthal GmbH | Pharmazeutische salze |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2005009329A2 (de) | 2005-02-03 |
| US20060121113A1 (en) | 2006-06-08 |
| DE10333835A1 (de) | 2005-03-10 |
| CA2533330A1 (en) | 2005-02-03 |
| US20100196473A1 (en) | 2010-08-05 |
| EP1648420A2 (de) | 2006-04-26 |
| WO2005009329A3 (de) | 2005-06-30 |
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