CA2087932A1 - Method of producing a solid dispersion of a sparingly water-soluble drug - Google Patents
Method of producing a solid dispersion of a sparingly water-soluble drugInfo
- Publication number
- CA2087932A1 CA2087932A1 CA002087932A CA2087932A CA2087932A1 CA 2087932 A1 CA2087932 A1 CA 2087932A1 CA 002087932 A CA002087932 A CA 002087932A CA 2087932 A CA2087932 A CA 2087932A CA 2087932 A1 CA2087932 A1 CA 2087932A1
- Authority
- CA
- Canada
- Prior art keywords
- solid dispersion
- water
- sparingly water
- soluble drug
- soluble
- 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.)
- Abandoned
Links
- 239000007962 solid dispersion Substances 0.000 title claims abstract description 44
- 229940079593 drug Drugs 0.000 title claims abstract description 43
- 239000003814 drug Substances 0.000 title claims abstract description 43
- 238000000034 method Methods 0.000 title claims description 34
- 229920003169 water-soluble polymer Polymers 0.000 claims abstract description 18
- 238000002156 mixing Methods 0.000 claims abstract description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 2
- 239000006185 dispersion Substances 0.000 abstract description 3
- 239000004480 active ingredient Substances 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 description 20
- 230000008569 process Effects 0.000 description 18
- FAIIFDPAEUKBEP-UHFFFAOYSA-N Nilvadipine Chemical compound COC(=O)C1=C(C#N)NC(C)=C(C(=O)OC(C)C)C1C1=CC=CC([N+]([O-])=O)=C1 FAIIFDPAEUKBEP-UHFFFAOYSA-N 0.000 description 14
- 229960005366 nilvadipine Drugs 0.000 description 14
- 239000002904 solvent Substances 0.000 description 10
- 238000010438 heat treatment Methods 0.000 description 9
- 229920002678 cellulose Polymers 0.000 description 8
- 239000001913 cellulose Substances 0.000 description 8
- 238000005516 engineering process Methods 0.000 description 8
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 8
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 8
- 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 8
- 238000002844 melting Methods 0.000 description 8
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 description 6
- 229960001597 nifedipine Drugs 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 238000004090 dissolution Methods 0.000 description 5
- 238000000227 grinding Methods 0.000 description 5
- 229940031703 low substituted hydroxypropyl cellulose Drugs 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 238000007922 dissolution test Methods 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 238000007499 fusion processing Methods 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000010298 pulverizing process Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 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
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- 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 2
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 2
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 2
- 229940071676 hydroxypropylcellulose Drugs 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- CPJSUEIXXCENMM-UHFFFAOYSA-N phenacetin Chemical compound CCOC1=CC=C(NC(C)=O)C=C1 CPJSUEIXXCENMM-UHFFFAOYSA-N 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- 244000215068 Acacia senegal Species 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
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- WDJUZGPOPHTGOT-OAXVISGBSA-N Digitoxin Natural products O([C@H]1[C@@H](C)O[C@@H](O[C@@H]2C[C@@H]3[C@@](C)([C@@H]4[C@H]([C@]5(O)[C@@](C)([C@H](C6=CC(=O)OC6)CC5)CC4)CC3)CC2)C[C@H]1O)[C@H]1O[C@@H](C)[C@H](O[C@H]2O[C@@H](C)[C@@H](O)[C@@H](O)C2)[C@@H](O)C1 WDJUZGPOPHTGOT-OAXVISGBSA-N 0.000 description 1
- IIUZTXTZRGLYTI-UHFFFAOYSA-N Dihydrogriseofulvin Natural products COC1CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 IIUZTXTZRGLYTI-UHFFFAOYSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- 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 description 1
- UXWOXTQWVMFRSE-UHFFFAOYSA-N Griseoviridin Natural products O=C1OC(C)CC=C(C(NCC=CC=CC(O)CC(O)C2)=O)SCC1NC(=O)C1=COC2=N1 UXWOXTQWVMFRSE-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- DDUHZTYCFQRHIY-UHFFFAOYSA-N Negwer: 6874 Natural products COC1=CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-UHFFFAOYSA-N 0.000 description 1
- CXOFVDLJLONNDW-UHFFFAOYSA-N Phenytoin Chemical compound N1C(=O)NC(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 CXOFVDLJLONNDW-UHFFFAOYSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 description 1
- 229960005091 chloramphenicol Drugs 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 1
- 229960003529 diazepam Drugs 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- WDJUZGPOPHTGOT-XUDUSOBPSA-N digitoxin Chemical compound C1[C@H](O)[C@H](O)[C@@H](C)O[C@H]1O[C@@H]1[C@@H](C)O[C@@H](O[C@@H]2[C@H](O[C@@H](O[C@@H]3C[C@@H]4[C@]([C@@H]5[C@H]([C@]6(CC[C@@H]([C@@]6(C)CC5)C=5COC(=O)C=5)O)CC4)(C)CC3)C[C@@H]2O)C)C[C@@H]1O WDJUZGPOPHTGOT-XUDUSOBPSA-N 0.000 description 1
- 229960000648 digitoxin Drugs 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- -1 etc.) Polymers 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- DDUHZTYCFQRHIY-RBHXEPJQSA-N griseofulvin Chemical compound COC1=CC(=O)C[C@@H](C)[C@@]11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-RBHXEPJQSA-N 0.000 description 1
- 229960002867 griseofulvin Drugs 0.000 description 1
- 239000001341 hydroxy propyl starch Substances 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 235000013828 hydroxypropyl starch Nutrition 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 229960003893 phenacetin Drugs 0.000 description 1
- 229960002036 phenytoin Drugs 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 238000009790 rate-determining step (RDS) Methods 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- 238000010977 unit operation Methods 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
- A61K9/10—Dispersions; Emulsions
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
-
- 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
- A61K9/146—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with organic macromolecular compounds
-
- 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
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nutrition Science (AREA)
- Physiology (AREA)
- Dispersion Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1079692 | 1992-01-24 | ||
| JP10796/1992 | 1992-01-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2087932A1 true CA2087932A1 (en) | 1993-07-25 |
Family
ID=11760311
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002087932A Abandoned CA2087932A1 (en) | 1992-01-24 | 1993-01-22 | Method of producing a solid dispersion of a sparingly water-soluble drug |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5340591A (enExample) |
| EP (1) | EP0552708A1 (enExample) |
| JP (1) | JPH05262642A (enExample) |
| KR (1) | KR930016091A (enExample) |
| CA (1) | CA2087932A1 (enExample) |
| TW (1) | TW259712B (enExample) |
Families Citing this family (151)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR960703335A (ko) * | 1993-06-30 | 1996-08-17 | 후지야마 아키라 | 캡슐화된 약제(encapsulated medicine) |
| DE4401646A1 (de) * | 1994-01-21 | 1995-07-27 | Krewel Werke Gmbh | Optimal freisetzende Kava-Extrakte |
| DE19504832A1 (de) * | 1995-02-14 | 1996-08-22 | Basf Ag | Feste Wirkstoff-Zubereitungen |
| DE19515972A1 (de) * | 1995-05-02 | 1996-11-07 | Bayer Ag | Arzneizubereitungen mit kontrollierter Freisetzung und Verfahren zu ihrer Herstellung |
| US5900425A (en) * | 1995-05-02 | 1999-05-04 | Bayer Aktiengesellschaft | Pharmaceutical preparations having controlled release of active compound and processes for their preparation |
| SE9502244D0 (sv) * | 1995-06-20 | 1995-06-20 | Bioglan Ab | A composition and a process for the preparation thereof |
| TW487582B (en) * | 1995-08-11 | 2002-05-21 | Nissan Chemical Ind Ltd | Method for converting sparingly water-soluble medical substance to amorphous state |
| EA001219B1 (ru) | 1996-05-20 | 2000-12-25 | Жансен Фармасетика Н.В. | Антигрибковые композиции с улучшенной биологической доступностью |
| AU3358397A (en) * | 1996-07-08 | 1998-02-02 | Kyowa Hakko Kogyo Co. Ltd. | Solid dispersions or solid dispersion preparations of tricyclic compounds |
| HN1998000115A (es) * | 1997-08-21 | 1999-06-02 | Warner Lambert Co | Formas de dosificación farmacéuticas sólidas |
| JPH11130698A (ja) * | 1997-10-31 | 1999-05-18 | Freunt Ind Co Ltd | アルギン酸多価金属塩球状微粒子集合体、該球状微粒子集合体に難溶性薬剤を担持した放出制御製剤及びそれらの製造方法 |
| IE980115A1 (en) * | 1998-02-16 | 2000-02-09 | Biovail Internat Ltd | Solubilizing delivery systems and method of manufacture |
| DE60039379D1 (de) * | 1999-02-10 | 2008-08-21 | Pfizer Prod Inc | Pharmazeutische feste Dispersionen |
| US6706283B1 (en) | 1999-02-10 | 2004-03-16 | Pfizer Inc | Controlled release by extrusion of solid amorphous dispersions of drugs |
| EP2415462A1 (en) * | 1999-12-23 | 2012-02-08 | Mayne Pharma International Pty Ltd. | Improved pharmaceutical compositions for poorly soluble drugs |
| US7115279B2 (en) * | 2000-08-03 | 2006-10-03 | Curatolo William J | Pharmaceutical compositions of cholesteryl ester transfer protein inhibitors |
| US20030099703A1 (en) * | 2000-08-11 | 2003-05-29 | Shigeru Aoki | Drug-containing solid dispersion having improved solubility |
| KR20020014570A (ko) * | 2000-08-18 | 2002-02-25 | 김충섭 | 고체분산화시킨 무정형 이프리플라본의 제조방법 |
| JP2004534811A (ja) * | 2001-06-22 | 2004-11-18 | ファイザー・プロダクツ・インク | ポリマーと薬剤の集合体を含む医薬組成物 |
| ES2333645T3 (es) * | 2001-06-22 | 2010-02-25 | Bend Research, Inc. | Composiciones farmaceuticas de dispersiones de medicamentos y polimeros neutros. |
| AR038375A1 (es) | 2002-02-01 | 2005-01-12 | Pfizer Prod Inc | Composiciones farmaceuticas de inhibidores de la proteina de transferencia de esteres de colesterilo |
| EP1920766B1 (en) | 2002-02-01 | 2017-08-23 | Bend Research, Inc | Pharmaceutical compositions of amorphous dispersions of drugs and lipophilic microphase-forming materials |
| JP2005522424A (ja) | 2002-02-01 | 2005-07-28 | ファイザー・プロダクツ・インク | コレステリルエステル転移タンパク質インヒビターの制御放出性薬剤投与形態 |
| KR20040011248A (ko) * | 2002-07-30 | 2004-02-05 | 환인제약 주식회사 | 암로디핀의 고체분산체와 그 제조방법 및 그를 포함하는약학적 조성물 |
| AU2003249474A1 (en) | 2002-08-12 | 2004-02-25 | Pfizer Products Inc. | Pharmaceutical compositions of semi-ordered drugs and polymers |
| JP2003146878A (ja) * | 2002-11-22 | 2003-05-21 | Sawai Pharmaceutical Co Ltd | ニルバジピン含有易溶性固形製剤およびその製造法 |
| ATE407670T1 (de) | 2002-12-20 | 2008-09-15 | Pfizer Prod Inc | Dosierungsform enthaltend einen cetp-hemmer und einen hmg-coa reduktase hemmer |
| WO2004069138A2 (en) * | 2003-02-03 | 2004-08-19 | Novartis Ag | Pharmaceutical formulation |
| WO2004110354A2 (en) * | 2003-05-15 | 2004-12-23 | Roskamp Research, Llc | Method for reducing amyloid deposition, amyloid neurotoxicity and microgliosis |
| MXPA06005489A (es) * | 2003-11-14 | 2006-08-11 | Pfizer Prod Inc | Dispersiones de solidos amorfos de un inhibidor de la mtp para el tratamiento de obesidad. |
| WO2005056542A1 (en) * | 2003-12-09 | 2005-06-23 | Pfizer Inc. | Compositions comprising an hiv protease inhibitor |
| AP2006003768A0 (en) | 2004-05-25 | 2006-10-31 | Pfizer Prod Inc | TetraazabenzoÄeÜazulene derivatives and analogs tehereof |
| KR20050119397A (ko) * | 2004-06-16 | 2005-12-21 | 보람제약주식회사 | 고상용해를 이용한 난용성 약물의 가용화 방법과 이를이용한 가용화 조성물 |
| GB0428152D0 (en) * | 2004-12-22 | 2005-01-26 | Novartis Ag | Organic compounds |
| EP2548894A1 (en) | 2005-02-03 | 2013-01-23 | Bend Research, Inc. | Pharmaceutical compositions with enhanced performance |
| JP2006347939A (ja) * | 2005-06-15 | 2006-12-28 | Tokyo Printing Ink Mfg Co Ltd | 薬物高分子複合体の製造方法及び薬物高分子複合体 |
| CN101272769B (zh) * | 2005-07-28 | 2013-04-24 | Isp投资有限公司 | 生物利用度提高的苯醌类化合物 |
| CN101583620B (zh) | 2005-11-28 | 2016-08-17 | 马里纳斯医药公司 | 加奈索酮组合物及其制备和使用方法 |
| JP2007308479A (ja) | 2006-04-20 | 2007-11-29 | Shin Etsu Chem Co Ltd | 固体分散体製剤 |
| JP2007308480A (ja) * | 2006-04-20 | 2007-11-29 | Shin Etsu Chem Co Ltd | 腸溶性固体分散体を含んでなる固形製剤 |
| US8343548B2 (en) | 2006-08-08 | 2013-01-01 | Shin-Etsu Chemical Co., Ltd. | Solid dosage form comprising solid dispersion |
| US8343547B2 (en) | 2006-08-08 | 2013-01-01 | Shin-Etsu Chemical Co., Ltd. | Solid dosage form comprising solid dispersion |
| EA018573B1 (ru) | 2006-09-22 | 2013-09-30 | Фармасайкликс, Инк. | Ингибиторы тирозинкиназы брутона |
| US20080085315A1 (en) * | 2006-10-10 | 2008-04-10 | John Alfred Doney | Amorphous ezetimibe and the production thereof |
| WO2008076780A2 (en) * | 2006-12-14 | 2008-06-26 | Isp Investments Inc. | Amorphous valsartan and the production thereof |
| US8613946B2 (en) * | 2006-12-21 | 2013-12-24 | Isp Investment Inc. | Carotenoids of enhanced bioavailability |
| US7638541B2 (en) | 2006-12-28 | 2009-12-29 | Metabolex Inc. | 5-ethyl-2-{4-[4-(4-tetrazol-1-yl-phenoxymethyl)-thiazol-2-yl]-piperidin-1-yl}-pyrimidine |
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| US2540253A (en) * | 1949-02-08 | 1951-02-06 | Merck & Co Inc | Granulation process |
| US2778768A (en) * | 1953-06-19 | 1957-01-22 | Rohm & Haas | Pesticidal ethylenebisdithiocarbamates with hydroxy ethyl cellulose compositions and methods |
| US2980589A (en) * | 1958-09-12 | 1961-04-18 | American Cyanamid Co | Process for producing anhydrous granulation of a medicinally active waterlabile powder |
| NL99185C (enExample) * | 1959-07-30 | |||
| US3692896A (en) * | 1968-06-14 | 1972-09-19 | Isumura Juntendo Co Ltd | Process for the preparation of water-soluble tablets |
| US4338322A (en) * | 1975-07-02 | 1982-07-06 | Fujisawa Pharmaceutical Co., Ltd. | 1,4-Dihydropyridine derivatives, pharmaceutical compositions containing same and methods of effecting vasodilation using same |
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1993
- 1993-01-04 US US08/000,300 patent/US5340591A/en not_active Expired - Fee Related
- 1993-01-18 JP JP5006129A patent/JPH05262642A/ja active Pending
- 1993-01-19 KR KR1019930000603A patent/KR930016091A/ko not_active Withdrawn
- 1993-01-19 EP EP93100699A patent/EP0552708A1/en not_active Withdrawn
- 1993-01-21 TW TW082100408A patent/TW259712B/zh active
- 1993-01-22 CA CA002087932A patent/CA2087932A1/en not_active Abandoned
Also Published As
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|---|---|
| KR930016091A (ko) | 1993-08-26 |
| EP0552708A1 (en) | 1993-07-28 |
| TW259712B (enExample) | 1995-10-11 |
| JPH05262642A (ja) | 1993-10-12 |
| US5340591A (en) | 1994-08-23 |
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