HRP20040613A2 - Oral solid solution formulation of a poorly water-soluble active substance - Google Patents
Oral solid solution formulation of a poorly water-soluble active substance Download PDFInfo
- Publication number
- HRP20040613A2 HRP20040613A2 HR20040613A HRP20040613A HRP20040613A2 HR P20040613 A2 HRP20040613 A2 HR P20040613A2 HR 20040613 A HR20040613 A HR 20040613A HR P20040613 A HRP20040613 A HR P20040613A HR P20040613 A2 HRP20040613 A2 HR P20040613A2
- Authority
- HR
- Croatia
- Prior art keywords
- mixture
- active substance
- formulation according
- polymer
- formulation
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 81
- 238000009472 formulation Methods 0.000 title claims description 48
- 239000013543 active substance Substances 0.000 title claims description 41
- 239000006104 solid solution Substances 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 32
- 239000004094 surface-active agent Substances 0.000 claims description 28
- 229920001223 polyethylene glycol Polymers 0.000 claims description 19
- 239000002775 capsule Substances 0.000 claims description 15
- 239000007788 liquid Substances 0.000 claims description 15
- 239000002202 Polyethylene glycol Substances 0.000 claims description 14
- 229920000620 organic polymer Polymers 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 229920002959 polymer blend Polymers 0.000 claims description 12
- -1 polyoxyethylene Polymers 0.000 claims description 11
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 10
- 239000012729 immediate-release (IR) formulation Substances 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 229920000136 polysorbate Polymers 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- 239000011575 calcium Substances 0.000 claims description 9
- 239000007903 gelatin capsule Substances 0.000 claims description 9
- 239000000243 solution Substances 0.000 claims description 9
- 229920000642 polymer Polymers 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 8
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 239000007884 disintegrant Substances 0.000 claims description 6
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 5
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 5
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 5
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 5
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 5
- VPSRQEHTHIMDQM-GZJHNZOKSA-N 2-[(3r)-3-[[(2r)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]-2-oxo-4,5-dihydro-3h-1-benzazepin-1-yl]acetic acid;hydrochloride Chemical compound Cl.C([C@H](C(=O)OCC)N[C@H]1C(N(CC(O)=O)C2=CC=CC=C2CC1)=O)CC1=CC=CC=C1 VPSRQEHTHIMDQM-GZJHNZOKSA-N 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 229910052736 halogen Chemical group 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 229910021645 metal ion Inorganic materials 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 241000499489 Castor canadensis Species 0.000 claims description 3
- 235000011779 Menyanthes trifoliata Nutrition 0.000 claims description 3
- 159000000007 calcium salts Chemical group 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229940068965 polysorbates Drugs 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229940088623 biologically active substance Drugs 0.000 claims description 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 2
- 239000000194 fatty acid Substances 0.000 claims description 2
- 229930195729 fatty acid Natural products 0.000 claims description 2
- 230000005660 hydrophilic surface Effects 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 239000004615 ingredient Substances 0.000 claims 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
- 229910052791 calcium Inorganic materials 0.000 claims 1
- 238000004090 dissolution Methods 0.000 description 12
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 9
- 229920000053 polysorbate 80 Polymers 0.000 description 9
- 239000008389 polyethoxylated castor oil Substances 0.000 description 8
- 239000008118 PEG 6000 Substances 0.000 description 7
- 229920002584 Polyethylene Glycol 6000 Polymers 0.000 description 7
- 229920001477 hydrophilic polymer Polymers 0.000 description 7
- 229920002685 Polyoxyl 35CastorOil Polymers 0.000 description 6
- QUANRIQJNFHVEU-UHFFFAOYSA-N oxirane;propane-1,2,3-triol Chemical compound C1CO1.OCC(O)CO QUANRIQJNFHVEU-UHFFFAOYSA-N 0.000 description 6
- 229920001030 Polyethylene Glycol 4000 Polymers 0.000 description 5
- 229910001424 calcium ion Inorganic materials 0.000 description 5
- 230000003111 delayed effect Effects 0.000 description 5
- 238000007922 dissolution test Methods 0.000 description 5
- 239000002552 dosage form Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229910001416 lithium ion Inorganic materials 0.000 description 4
- 229910001425 magnesium ion Inorganic materials 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 229910001415 sodium ion Inorganic materials 0.000 description 3
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000001506 calcium phosphate Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229940078499 tricalcium phosphate Drugs 0.000 description 2
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 2
- 235000019731 tricalcium phosphate Nutrition 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- LQIAZOCLNBBZQK-UHFFFAOYSA-N 1-(1,2-Diphosphanylethyl)pyrrolidin-2-one Chemical compound PCC(P)N1CCCC1=O LQIAZOCLNBBZQK-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- 229920000858 Cyclodextrin Polymers 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
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 229920003085 Kollidon® CL Polymers 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229920003110 Primojel Polymers 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical class O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007963 capsule composition Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229940097362 cyclodextrins Drugs 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- 210000002249 digestive system Anatomy 0.000 description 1
- 239000012738 dissolution medium Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000009506 drug dissolution testing Methods 0.000 description 1
- 229940088679 drug related substance Drugs 0.000 description 1
- 239000007904 elastic gelatin capsule Substances 0.000 description 1
- MVPICKVDHDWCJQ-UHFFFAOYSA-N ethyl 3-pyrrolidin-1-ylpropanoate Chemical compound CCOC(=O)CCN1CCCC1 MVPICKVDHDWCJQ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 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 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 239000007932 molded tablet Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229940093429 polyethylene glycol 6000 Drugs 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229940045902 sodium stearyl fumarate Drugs 0.000 description 1
- 239000007962 solid dispersion Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4858—Organic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
-
- 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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
-
- 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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4866—Organic macromolecular compounds
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Inorganic Chemistry (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02075623 | 2002-02-14 | ||
| PCT/EP2003/050014 WO2003068266A1 (en) | 2002-02-14 | 2003-02-11 | Oral solid solution formulation of a poorly water-soluble active substance |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20040613A2 true HRP20040613A2 (en) | 2005-04-30 |
Family
ID=27619166
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20040613A HRP20040613A2 (en) | 2002-02-14 | 2004-07-06 | Oral solid solution formulation of a poorly water-soluble active substance |
Country Status (25)
| Country | Link |
|---|---|
| US (2) | US20050008697A1 (ja) |
| EP (1) | EP1476196B1 (ja) |
| JP (1) | JP2005517041A (ja) |
| KR (1) | KR101014545B1 (ja) |
| CN (1) | CN1273194C (ja) |
| AR (1) | AR038681A1 (ja) |
| AT (1) | ATE345817T1 (ja) |
| AU (1) | AU2003208713B2 (ja) |
| BR (1) | BR0307278A (ja) |
| CA (1) | CA2472744A1 (ja) |
| DE (1) | DE60309839T2 (ja) |
| DK (1) | DK1476196T3 (ja) |
| ES (1) | ES2277635T3 (ja) |
| HK (1) | HK1077218A1 (ja) |
| HR (1) | HRP20040613A2 (ja) |
| IL (2) | IL162883A0 (ja) |
| MX (1) | MXPA04007852A (ja) |
| NO (1) | NO20043832L (ja) |
| PL (1) | PL370452A1 (ja) |
| PT (1) | PT1476196E (ja) |
| RU (1) | RU2314811C2 (ja) |
| SI (1) | SI1476196T1 (ja) |
| UA (1) | UA79267C2 (ja) |
| WO (1) | WO2003068266A1 (ja) |
| ZA (1) | ZA200405608B (ja) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004062692A1 (en) * | 2003-01-13 | 2004-07-29 | Solvay Pharmaceuticals B.V. | Formulation of poorly water-soluble active substances |
| US8025899B2 (en) | 2003-08-28 | 2011-09-27 | Abbott Laboratories | Solid pharmaceutical dosage form |
| US8377952B2 (en) * | 2003-08-28 | 2013-02-19 | Abbott Laboratories | Solid pharmaceutical dosage formulation |
| US20050267124A1 (en) * | 2004-05-14 | 2005-12-01 | Solvay Pharmaceuticals Gmbh | Pharmaceutical compositions comprising NEP-inhibitors, inhibitors of the endogenous producing system and PDEV inhibiitors |
| US20060159748A1 (en) * | 2004-12-23 | 2006-07-20 | Rajesh Jain | Oral immediate release formulation of a poorly water-soluble active substance |
| TW200633713A (en) * | 2004-12-23 | 2006-10-01 | Solvay Pharm Bv | Oral immediate release formulation of a poorly water-soluble active substance |
| WO2007054975A1 (en) * | 2005-11-08 | 2007-05-18 | Panacea Biotec Ltd | Pharmaceutical compositions for the treatment of cardiovascular and other associated disorders |
| US8497258B2 (en) | 2005-11-12 | 2013-07-30 | The Regents Of The University Of California | Viscous budesonide for the treatment of inflammatory diseases of the gastrointestinal tract |
| JP2007308479A (ja) | 2006-04-20 | 2007-11-29 | Shin Etsu Chem Co Ltd | 固体分散体製剤 |
| WO2007144418A1 (en) * | 2006-06-16 | 2007-12-21 | Solvay Pharmaceuticals B.V. | Oral pharmaceutical composition of a poorly water-soluble active substance |
| KR20090033246A (ko) * | 2006-06-22 | 2009-04-01 | 솔베이 파마슈티칼스 비. 브이 | 수용성이 불량한 활성 물질의 경구용 약제학적 조성물 |
| AU2007271088A1 (en) * | 2006-07-06 | 2008-01-10 | Ares Trading S.A. | An oral pharmaceutical composition of an anilinopyrimidine, its preparation and use thereof |
| CA2662315A1 (en) * | 2006-09-01 | 2008-03-06 | Teva Pharmaceutical Industries Ltd. | Solid composites of a calcium receptor-active compound |
| AR071375A1 (es) * | 2008-04-22 | 2010-06-16 | Solvay Pharm Gmbh | Formulaciones para ingredientes farmaceuticos activos de permeabilidad deficiente, proceso de preparacion y producto |
| CA2765033C (en) * | 2009-06-12 | 2020-07-14 | Meritage Pharma, Inc. | Methods for treating gastrointestinal disorders |
| HUE039328T2 (hu) | 2010-08-04 | 2018-12-28 | Gruenenthal Gmbh | 6'-Fluor-(N-metil- vagy N,N-dimetil-)-4-fenil-4',9'-dihidro-3'H-spiro[ciklohexán-1,1'pirano[3,4,B]indol]-4-amin összetételû gyógyszerészeti adagolási forma a neuropátiás fájdalom kezelésére |
| KR101828768B1 (ko) * | 2010-08-04 | 2018-02-13 | 그뤼넨탈 게엠베하 | ６’플루오로（Ｎ메틸 또는 Ｎ，Ｎ디메틸）４페닐４’，９’디하이드로３’Ｈ스피로［사이클로헥산１，１’피라노［３，４，ｂ］인돌］４아민을 포함하는 약제학적 투여형 |
| US20180185399A1 (en) * | 2015-07-03 | 2018-07-05 | Zhejiang Hisun Pharmaceutical Co., Ltd. | Ginsenoside c-k oral solid preparation and preparation method thereof |
| PL424452A1 (pl) | 2018-01-31 | 2019-08-12 | Forty-Four Pharmaceuticals Spółka Z Ograniczoną Odpowiedzialnością | Inhibitory obojętnej endopeptydazy (NEP) i ludzkiej rozpuszczalnej endopeptydazy (hSEP) do profilaktyki i leczenia chorób oczu |
| WO2020112961A1 (en) | 2018-11-30 | 2020-06-04 | Chemocentryx, Inc. | Capsule formulations |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3359167A (en) * | 1965-07-22 | 1967-12-19 | Pfizer & Co C | Vitamin a compositions |
| US4325970A (en) * | 1980-10-09 | 1982-04-20 | Hoffmann-La Roche Inc. | 15-Acetyl-prostaglandins |
| NZ224497A (en) * | 1987-05-18 | 1990-04-26 | Janssen Pharmaceutica Nv | Pharmaceutical composition comprising flunarizine |
| US5281420A (en) * | 1992-05-19 | 1994-01-25 | The Procter & Gamble Company | Solid dispersion compositions of tebufelone |
| DE19510566A1 (de) * | 1995-03-23 | 1996-09-26 | Kali Chemie Pharma Gmbh | Benzazepin-, Benzoxazepin- und Benzothiazepin-N-essigsäurederivate sowie Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| DE19638020A1 (de) * | 1996-09-18 | 1998-03-19 | Solvay Pharm Gmbh | Die gastrointestinale Durchblutung fördernde Arzneimittel |
| TW426516B (en) * | 1996-12-06 | 2001-03-21 | Fujisawa Pharmaceutical Co | An oral pharmaceutical composition in solid dispersion containing water-insoluble tricyclic compounds |
| ES2229473T3 (es) * | 1997-01-30 | 2005-04-16 | Novartis Ag | Composiciones farmaceuticas sin aceite que contienen ciclosporina a. |
| US6008191A (en) * | 1997-09-08 | 1999-12-28 | Panacea Biotec Limited | Pharmaceutical compositions containing cyclosporin |
| KR100336090B1 (ko) * | 1998-06-27 | 2002-05-27 | 윤승원 | 오일, 지방산 또는 이들의 혼합물을 함유한 난용성 약물의 고형분산제제 |
| DE19906310A1 (de) * | 1999-02-16 | 2000-08-17 | Solvay Pharm Gmbh | Arzneimittel zur Behandlung von Bluthochdruck |
| DE19932555A1 (de) * | 1999-07-13 | 2001-01-18 | Solvay Pharm Gmbh | Arzneimittel mit protektiver Wirkung gegen oxidativ-toxische und insbesondere gegen kardiotoxische Substanzen |
| US20010036959A1 (en) * | 2000-04-03 | 2001-11-01 | Gabel Rolf Dieter | Carvedilol-hydrophilic solutions |
-
2003
- 2003-02-04 AR ARP030100341A patent/AR038681A1/es unknown
- 2003-02-11 CA CA002472744A patent/CA2472744A1/en not_active Abandoned
- 2003-02-11 EP EP03706620A patent/EP1476196B1/en not_active Expired - Lifetime
- 2003-02-11 DE DE60309839T patent/DE60309839T2/de not_active Expired - Lifetime
- 2003-02-11 ES ES03706620T patent/ES2277635T3/es not_active Expired - Lifetime
- 2003-02-11 AT AT03706620T patent/ATE345817T1/de active
- 2003-02-11 BR BR0307278-9A patent/BR0307278A/pt not_active Application Discontinuation
- 2003-02-11 DK DK03706620T patent/DK1476196T3/da active
- 2003-02-11 PT PT03706620T patent/PT1476196E/pt unknown
- 2003-02-11 IL IL16288303A patent/IL162883A0/xx unknown
- 2003-02-11 AU AU2003208713A patent/AU2003208713B2/en not_active Ceased
- 2003-02-11 JP JP2003567446A patent/JP2005517041A/ja active Pending
- 2003-02-11 WO PCT/EP2003/050014 patent/WO2003068266A1/en active IP Right Grant
- 2003-02-11 SI SI200330630T patent/SI1476196T1/sl unknown
- 2003-02-11 MX MXPA04007852A patent/MXPA04007852A/es active IP Right Grant
- 2003-02-11 KR KR1020047012635A patent/KR101014545B1/ko not_active IP Right Cessation
- 2003-02-11 RU RU2004127457/15A patent/RU2314811C2/ru not_active IP Right Cessation
- 2003-02-11 CN CNB038038978A patent/CN1273194C/zh not_active Expired - Fee Related
- 2003-02-11 PL PL03370452A patent/PL370452A1/xx not_active IP Right Cessation
- 2003-11-02 UA UA20040907457A patent/UA79267C2/uk unknown
-
2004
- 2004-07-06 HR HR20040613A patent/HRP20040613A2/hr not_active Application Discontinuation
- 2004-07-06 IL IL162883A patent/IL162883A/en not_active IP Right Cessation
- 2004-07-14 ZA ZA200405608A patent/ZA200405608B/en unknown
- 2004-08-11 US US10/915,560 patent/US20050008697A1/en not_active Abandoned
- 2004-09-13 NO NO20043832A patent/NO20043832L/no not_active Application Discontinuation
-
2005
- 2005-10-20 HK HK05109356A patent/HK1077218A1/xx not_active IP Right Cessation
-
2010
- 2010-11-12 US US12/945,570 patent/US20110086844A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| CN1633307A (zh) | 2005-06-29 |
| PL370452A1 (en) | 2005-05-30 |
| IL162883A (en) | 2009-05-04 |
| AU2003208713A1 (en) | 2003-09-04 |
| WO2003068266A1 (en) | 2003-08-21 |
| EP1476196A1 (en) | 2004-11-17 |
| EP1476196B1 (en) | 2006-11-22 |
| CN1273194C (zh) | 2006-09-06 |
| KR20040085193A (ko) | 2004-10-07 |
| IL162883A0 (en) | 2005-11-20 |
| DE60309839D1 (de) | 2007-01-04 |
| KR101014545B1 (ko) | 2011-02-16 |
| BR0307278A (pt) | 2004-12-28 |
| CA2472744A1 (en) | 2003-08-21 |
| DK1476196T3 (da) | 2007-03-05 |
| JP2005517041A (ja) | 2005-06-09 |
| US20050008697A1 (en) | 2005-01-13 |
| NO20043832L (no) | 2004-09-13 |
| AR038681A1 (es) | 2005-01-26 |
| HK1077218A1 (en) | 2006-02-10 |
| UA79267C2 (en) | 2007-06-11 |
| ZA200405608B (en) | 2005-06-24 |
| RU2314811C2 (ru) | 2008-01-20 |
| US20110086844A1 (en) | 2011-04-14 |
| AU2003208713B2 (en) | 2007-10-18 |
| SI1476196T1 (sl) | 2007-04-30 |
| MXPA04007852A (es) | 2004-10-15 |
| DE60309839T2 (de) | 2007-03-15 |
| RU2004127457A (ru) | 2005-04-20 |
| ES2277635T3 (es) | 2007-07-16 |
| PT1476196E (pt) | 2007-02-28 |
| ATE345817T1 (de) | 2006-12-15 |
| AU2003208713B9 (en) | 2003-09-04 |
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