JP2006511536A - 水貧溶性薬物のバイオアベイラビリティーを改善する自由流動性固形製剤およびその製造方法 - Google Patents
水貧溶性薬物のバイオアベイラビリティーを改善する自由流動性固形製剤およびその製造方法 Download PDFInfo
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- OIALAIQRYISUEV-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]e Polymers CCCCCCCCCCCCCCCCCC(=O)OCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO OIALAIQRYISUEV-UHFFFAOYSA-N 0.000 description 4
- 229920002685 Polyoxyl 35CastorOil Polymers 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
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- 239000000839 emulsion Substances 0.000 description 3
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- WPMWEFXCIYCJSA-UHFFFAOYSA-N Tetraethylene glycol monododecyl ether Chemical compound CCCCCCCCCCCCOCCOCCOCCOCCO WPMWEFXCIYCJSA-UHFFFAOYSA-N 0.000 description 2
- 239000001506 calcium phosphate Substances 0.000 description 2
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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
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- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 235000015872 dietary supplement Nutrition 0.000 description 1
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- 229960000273 oxametacin Drugs 0.000 description 1
- QUANRIQJNFHVEU-UHFFFAOYSA-N oxirane;propane-1,2,3-triol Chemical compound C1CO1.OCC(O)CO QUANRIQJNFHVEU-UHFFFAOYSA-N 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000008389 polyethoxylated castor oil Substances 0.000 description 1
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- 150000003431 steroids Chemical group 0.000 description 1
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- 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 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
- A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
- A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
-
- 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
- A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
-
- 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
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1611—Inorganic 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
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2072—Pills, tablets, discs, rods characterised by shape, structure or size; Tablets with holes, special break lines or identification marks; Partially coated tablets; Disintegrating flat shaped forms
- A61K9/2077—Tablets comprising drug-containing microparticles in a substantial amount of supporting matrix; Multiparticulate tablets
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- 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
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1617—Organic compounds, e.g. phospholipids, fats
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Inorganic Chemistry (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/317,657 US20040115226A1 (en) | 2002-12-12 | 2002-12-12 | Free-flowing solid formulations with improved bio-availability of poorly water soluble drugs and process for making the same |
| PCT/US2003/038979 WO2004054540A2 (en) | 2002-12-12 | 2003-12-09 | Solid compositions with improved bio-availability of insoluble or poorly water soluble drugs and a corresponding process for preparing such |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006511536A true JP2006511536A (ja) | 2006-04-06 |
| JP2006511536A5 JP2006511536A5 (cg-RX-API-DMAC7.html) | 2006-09-21 |
Family
ID=32506185
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004560372A Pending JP2006511536A (ja) | 2002-12-12 | 2003-12-09 | 水貧溶性薬物のバイオアベイラビリティーを改善する自由流動性固形製剤およびその製造方法 |
Country Status (4)
| Country | Link |
|---|---|
| US (3) | US20040115226A1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP2006511536A (cg-RX-API-DMAC7.html) |
| AU (1) | AU2003300833A1 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2004054540A2 (cg-RX-API-DMAC7.html) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007191396A (ja) * | 2005-01-07 | 2007-08-02 | Rohto Pharmaceut Co Ltd | 皮膚外用剤 |
| KR20210146290A (ko) * | 2019-02-12 | 2021-12-03 | 스미토모 다이니폰 파마 온콜로지, 인크. | 헤테로시클릭 단백질 키나제 억제제를 포함하는 제제 |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101152470B1 (ko) | 2003-08-13 | 2012-06-01 | 바이오콘 리미티드 | 치료제용 마이크로-입자 지방산 염 고형 투약 제형 |
| WO2005018607A1 (ja) * | 2003-08-20 | 2005-03-03 | Ajinomoto Co., Inc. | 溶解性を改善した医薬品製剤 |
| US20050220825A1 (en) * | 2004-03-10 | 2005-10-06 | Adrian Funke | Molecular dispersions of drospirenone |
| WO2005105040A2 (en) * | 2004-04-26 | 2005-11-10 | Micelle Products, Inc. | Water-soluble formulations of fat soluble vitamins and pharmaceutical agents and their applications |
| GB0612809D0 (en) * | 2006-06-28 | 2006-08-09 | Univ Sunderland | Formulation |
| US20100061969A1 (en) * | 2006-11-22 | 2010-03-11 | Asahi Kasei Pharma Corporation | Dietary supplement, anti-fatigue agent or physical endurance enhancer, functional food, or cosmetic |
| WO2009070978A1 (fr) * | 2007-11-22 | 2009-06-11 | Yu He | Libération rapide dans la cavité buccale des produits de santé et procédé de préparation associé |
| EP2111854A1 (en) | 2008-04-22 | 2009-10-28 | Lek Pharmaceuticals D.D. | Self-microemulsifying systems incorporated into liquid core microcapsules |
| WO2010098906A1 (en) * | 2009-02-24 | 2010-09-02 | Madeira Therapeutics | Liquid statin formulations |
| ES2363965B1 (es) | 2009-11-20 | 2013-01-24 | Gp Pharm S.A. | Cápsulas de principios activos betabloqueantes y ésteres de ácidos grasos poliinsaturados. |
| ES2363964B1 (es) | 2009-11-20 | 2012-08-22 | Gp Pharm, S.A. | Cápsulas de principios activos farmacéuticos y ésteres de ácidos grasos poliinsaturados. |
| US20110160168A1 (en) | 2009-12-31 | 2011-06-30 | Differential Drug Development Associates, Llc | Modulation of solubility, stability, absorption, metabolism, and pharmacokinetic profile of lipophilic drugs by sterols |
| JP2013540827A (ja) | 2010-10-29 | 2013-11-07 | ウエスタン ユニバーシティ オブ ヘルス サイエンシズ | 三種混合製剤 |
| US9757388B2 (en) | 2011-05-13 | 2017-09-12 | Acerus Pharmaceuticals Srl | Intranasal methods of treating women for anorgasmia with 0.6% and 0.72% testosterone gels |
| US20130045958A1 (en) | 2011-05-13 | 2013-02-21 | Trimel Pharmaceuticals Corporation | Intranasal 0.15% and 0.24% testosterone gel formulations and use thereof for treating anorgasmia or hypoactive sexual desire disorder |
| US20130040923A1 (en) | 2011-05-13 | 2013-02-14 | Trimel Pharmaceuticals Corporation | Intranasal lower dosage strength testosterone gel formulations and use thereof for treating anorgasmia or hypoactive sexual desire disorder |
| EP2782584B1 (en) | 2011-11-23 | 2021-06-09 | TherapeuticsMD, Inc. | Natural combination hormone replacement formulations and therapies |
| US9301920B2 (en) | 2012-06-18 | 2016-04-05 | Therapeuticsmd, Inc. | Natural combination hormone replacement formulations and therapies |
| CA2872779A1 (en) | 2012-05-09 | 2013-11-14 | Western University Of Health Sciences | Proliposomal testosterone formulations |
| US20130338122A1 (en) | 2012-06-18 | 2013-12-19 | Therapeuticsmd, Inc. | Transdermal hormone replacement therapies |
| US10806740B2 (en) | 2012-06-18 | 2020-10-20 | Therapeuticsmd, Inc. | Natural combination hormone replacement formulations and therapies |
| US10806697B2 (en) | 2012-12-21 | 2020-10-20 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| US20150196640A1 (en) | 2012-06-18 | 2015-07-16 | Therapeuticsmd, Inc. | Progesterone formulations having a desirable pk profile |
| US9180091B2 (en) | 2012-12-21 | 2015-11-10 | Therapeuticsmd, Inc. | Soluble estradiol capsule for vaginal insertion |
| US10537581B2 (en) | 2012-12-21 | 2020-01-21 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| US11266661B2 (en) | 2012-12-21 | 2022-03-08 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| US11246875B2 (en) | 2012-12-21 | 2022-02-15 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| US10568891B2 (en) | 2012-12-21 | 2020-02-25 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| US10471072B2 (en) | 2012-12-21 | 2019-11-12 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| US11744838B2 (en) | 2013-03-15 | 2023-09-05 | Acerus Biopharma Inc. | Methods of treating hypogonadism with transnasal testosterone bio-adhesive gel formulations in male with allergic rhinitis, and methods for preventing an allergic rhinitis event |
| WO2014143127A1 (en) | 2013-03-15 | 2014-09-18 | Differential Drug Development Associates Llc | Emulsion formulations |
| US20140370084A1 (en) * | 2013-06-18 | 2014-12-18 | Therapeuticsmd, Inc. | Estradiol formulations and therapies |
| AR100562A1 (es) | 2014-05-22 | 2016-10-12 | Therapeuticsmd Inc | Composición farmacéutica de estradiol y progesterona para terapia de reemplazo hormonal |
| US10328087B2 (en) | 2015-07-23 | 2019-06-25 | Therapeuticsmd, Inc. | Formulations for solubilizing hormones |
| KR20180126582A (ko) | 2016-04-01 | 2018-11-27 | 쎄러퓨틱스엠디, 인코퍼레이티드 | 스테로이드 호르몬 약제학적 조성물 |
| WO2017173044A1 (en) | 2016-04-01 | 2017-10-05 | Therapeuticsmd Inc. | Steroid hormone compositions in medium chain oils |
| US12403146B2 (en) | 2019-10-30 | 2025-09-02 | Marius Pharmaceuticals, Inc. | Preferred oral testosterone undecanoate therapy to achieve testosterone replacement treatment |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59148718A (ja) * | 1983-02-10 | 1984-08-25 | Fujisawa Pharmaceut Co Ltd | ユビデカレノン組成物 |
| JP2002522473A (ja) * | 1998-08-13 | 2002-07-23 | シーマ・ラブス・インコーポレイテッド | 経口投与の固形投与形態物としてのマイクロエマルション |
| JP2002537317A (ja) * | 1999-02-26 | 2002-11-05 | リポシン インコーポレイテッド | 疎水性治療剤の改善された送達のための組成物および方法 |
| JP2005516991A (ja) * | 2002-02-01 | 2005-06-09 | ミセル・プロダクツ・インコーポレイテッド | 白板症を処置するためのβカロチン澄明ミセル化製剤 |
Family Cites Families (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4572915A (en) * | 1984-05-01 | 1986-02-25 | Bioglan Laboratories | Clear micellized solutions of fat soluble essential nutrients |
| US4874795A (en) * | 1985-04-02 | 1989-10-17 | Yesair David W | Composition for delivery of orally administered drugs and other substances |
| US4900734A (en) * | 1987-08-27 | 1990-02-13 | Maxson Wayne S | Novel pharmaceutical composition containing estradiol and progesterone for oral administration |
| DE69229779T2 (de) * | 1991-04-19 | 1999-12-23 | Lds Technologies, Inc. | Konvertierbare mikroemulsionsverbindungen |
| US6312704B1 (en) * | 1993-09-30 | 2001-11-06 | Gattefosse, S.A. | Orally administrable composition capable of providing enhanced bioavailability when ingested |
| US6054136A (en) * | 1993-09-30 | 2000-04-25 | Gattefosse S.A. | Orally administrable composition capable of providing enhanced bioavailability when ingested |
| FR2714621B1 (fr) * | 1994-01-06 | 1996-02-23 | Centre Nat Rech Scient | Procédé de préparation de liposomes sans utilisation de solvant organique. |
| US5938990A (en) * | 1994-07-01 | 1999-08-17 | Roche Vitamins Inc. | Encapsulation of oleophilic substances and compositions produced thereby |
| US5863919A (en) * | 1994-07-25 | 1999-01-26 | University Of South Florida | Lock and key micelles and monomer building blocks therefor |
| US5908635A (en) * | 1994-08-05 | 1999-06-01 | The United States Of America As Represented By The Department Of Health And Human Services | Method for the liposomal delivery of nucleic acids |
| US6120794A (en) * | 1995-09-26 | 2000-09-19 | University Of Pittsburgh | Emulsion and micellar formulations for the delivery of biologically active substances to cells |
| IL117773A (en) * | 1996-04-02 | 2000-10-31 | Pharmos Ltd | Solid lipid compositions of coenzyme Q10 for enhanced oral bioavailability |
| US5993858A (en) * | 1996-06-14 | 1999-11-30 | Port Systems L.L.C. | Method and formulation for increasing the bioavailability of poorly water-soluble drugs |
| US5827533A (en) * | 1997-02-06 | 1998-10-27 | Duke University | Liposomes containing active agents aggregated with lipid surfactants |
| IT1289939B1 (it) * | 1997-02-20 | 1998-10-19 | Angelini Ricerche Spa | Composizione farmaceutica acquosa comprendente un principio attivo altamente insolubile in acqua |
| US6322810B1 (en) * | 1997-07-14 | 2001-11-27 | Hayat Alkan-Onyuksel | Materials and methods for making improved micelle compositions |
| IT1294205B1 (it) * | 1997-07-23 | 1999-03-24 | Farmigea Spa | Procedimento per la solubilizzazione in acqua e in veicoli acquosi di sostanze farmacologicamente attive |
| US6027747A (en) * | 1997-11-11 | 2000-02-22 | Terracol; Didier | Process for the production of dry pharmaceutical forms and the thus obtained pharmaceutical compositions |
| CN1281355A (zh) * | 1997-12-12 | 2001-01-24 | 三阳株式会社 | 用于基因递送的生物可降解性混合聚合胶束 |
| US6013665A (en) * | 1997-12-16 | 2000-01-11 | Abbott Laboratories | Method for enhancing the absorption and transport of lipid soluble compounds using structured glycerides |
| US6017545A (en) * | 1998-02-10 | 2000-01-25 | Modi; Pankaj | Mixed micellar delivery system and method of preparation |
| FR2782006B1 (fr) * | 1998-08-07 | 2002-04-19 | Gattefosse Ets Sa | Composition a liberation prolongee apte a former une micro-emulsion |
| AU3227000A (en) * | 1999-02-10 | 2000-08-29 | Ontogeny, Inc. | Methods of inducing insulin positive progenitor cells |
| US6248363B1 (en) * | 1999-11-23 | 2001-06-19 | Lipocine, Inc. | Solid carriers for improved delivery of active ingredients in pharmaceutical compositions |
| GB9908309D0 (en) * | 1999-04-12 | 1999-06-02 | Phares Pharm Res Nv | Lipid aggregate forming compositions and their use |
| US6248360B1 (en) * | 2000-06-21 | 2001-06-19 | International Health Management Associates, Inc. | Complexes to improve oral absorption of poorly absorbable antibiotics |
-
2002
- 2002-12-12 US US10/317,657 patent/US20040115226A1/en not_active Abandoned
-
2003
- 2003-12-09 JP JP2004560372A patent/JP2006511536A/ja active Pending
- 2003-12-09 WO PCT/US2003/038979 patent/WO2004054540A2/en not_active Ceased
- 2003-12-09 AU AU2003300833A patent/AU2003300833A1/en not_active Abandoned
-
2006
- 2006-07-27 US US11/494,131 patent/US20060263397A1/en not_active Abandoned
- 2006-07-27 US US11/494,129 patent/US20070009559A1/en not_active Abandoned
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59148718A (ja) * | 1983-02-10 | 1984-08-25 | Fujisawa Pharmaceut Co Ltd | ユビデカレノン組成物 |
| JP2002522473A (ja) * | 1998-08-13 | 2002-07-23 | シーマ・ラブス・インコーポレイテッド | 経口投与の固形投与形態物としてのマイクロエマルション |
| JP2002537317A (ja) * | 1999-02-26 | 2002-11-05 | リポシン インコーポレイテッド | 疎水性治療剤の改善された送達のための組成物および方法 |
| JP2005516991A (ja) * | 2002-02-01 | 2005-06-09 | ミセル・プロダクツ・インコーポレイテッド | 白板症を処置するためのβカロチン澄明ミセル化製剤 |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007191396A (ja) * | 2005-01-07 | 2007-08-02 | Rohto Pharmaceut Co Ltd | 皮膚外用剤 |
| KR20210146290A (ko) * | 2019-02-12 | 2021-12-03 | 스미토모 다이니폰 파마 온콜로지, 인크. | 헤테로시클릭 단백질 키나제 억제제를 포함하는 제제 |
| JP2022520361A (ja) * | 2019-02-12 | 2022-03-30 | スミトモ ダイニッポン ファーマ オンコロジー， インコーポレイテッド | 複素環式タンパク質キナーゼ阻害剤を含む製剤 |
| JP7662528B2 (ja) | 2019-02-12 | 2025-04-15 | スミトモ ファーマ アメリカ， インコーポレイテッド | 複素環式タンパク質キナーゼ阻害剤を含む製剤 |
| KR102904026B1 (ko) | 2019-02-12 | 2025-12-26 | 스미토모 파마 아메리카, 인크. | 헤테로시클릭 단백질 키나제 억제제를 포함하는 제제 |
Also Published As
| Publication number | Publication date |
|---|---|
| US20070009559A1 (en) | 2007-01-11 |
| US20060263397A1 (en) | 2006-11-23 |
| AU2003300833A8 (en) | 2004-07-09 |
| WO2004054540A2 (en) | 2004-07-01 |
| WO2004054540A3 (en) | 2004-09-30 |
| US20040115226A1 (en) | 2004-06-17 |
| AU2003300833A1 (en) | 2004-07-09 |
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