JP2008531721A - 複素環式アミド誘導体のナノ粒子状組成物 - Google Patents
複素環式アミド誘導体のナノ粒子状組成物 Download PDFInfo
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- JP2008531721A JP2008531721A JP2007558231A JP2007558231A JP2008531721A JP 2008531721 A JP2008531721 A JP 2008531721A JP 2007558231 A JP2007558231 A JP 2007558231A JP 2007558231 A JP2007558231 A JP 2007558231A JP 2008531721 A JP2008531721 A JP 2008531721A
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- Prior art keywords
- zafirlukast
- chloride
- composition
- bromide
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- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 409
- -1 heterocyclic amide Chemical class 0.000 title claims abstract description 309
- YEEZWCHGZNKEEK-UHFFFAOYSA-N Zafirlukast Chemical compound COC1=CC(C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C)=CC=C1CC(C1=C2)=CN(C)C1=CC=C2NC(=O)OC1CCCC1 YEEZWCHGZNKEEK-UHFFFAOYSA-N 0.000 claims abstract description 352
- 229960004764 zafirlukast Drugs 0.000 claims abstract description 339
- 239000002245 particle Substances 0.000 claims abstract description 144
- 238000013270 controlled release Methods 0.000 claims abstract description 53
- 239000002105 nanoparticle Substances 0.000 claims abstract description 45
- 239000003814 drug Substances 0.000 claims abstract description 43
- 229940079593 drug Drugs 0.000 claims abstract description 37
- 238000011282 treatment Methods 0.000 claims abstract description 35
- 208000006673 asthma Diseases 0.000 claims abstract description 34
- 239000012729 immediate-release (IR) formulation Substances 0.000 claims abstract description 29
- 239000004480 active ingredient Substances 0.000 claims abstract description 25
- 230000003204 osmotic effect Effects 0.000 claims abstract description 11
- 238000009792 diffusion process Methods 0.000 claims abstract description 10
- 238000009472 formulation Methods 0.000 claims description 105
- 239000003381 stabilizer Substances 0.000 claims description 95
- 238000000034 method Methods 0.000 claims description 91
- 239000002552 dosage form Substances 0.000 claims description 38
- 239000011248 coating agent Substances 0.000 claims description 35
- 239000006185 dispersion Substances 0.000 claims description 32
- 238000000576 coating method Methods 0.000 claims description 31
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 29
- 229920000642 polymer Polymers 0.000 claims description 27
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 24
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- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 20
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims description 19
- 239000011159 matrix material Substances 0.000 claims description 19
- 235000019333 sodium laurylsulphate Nutrition 0.000 claims description 19
- 125000002091 cationic group Chemical group 0.000 claims description 18
- 238000004090 dissolution Methods 0.000 claims description 18
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 claims description 17
- AISMNBXOJRHCIA-UHFFFAOYSA-N trimethylazanium;bromide Chemical compound Br.CN(C)C AISMNBXOJRHCIA-UHFFFAOYSA-N 0.000 claims description 17
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- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 claims description 15
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 14
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 13
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 claims description 13
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 11
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 11
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- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 10
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- 239000001913 cellulose Substances 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 10
- 150000003904 phospholipids Chemical class 0.000 claims description 10
- 108010010803 Gelatin Proteins 0.000 claims description 9
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 9
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 9
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- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 9
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 claims description 9
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- JBIROUFYLSSYDX-UHFFFAOYSA-M benzododecinium chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 JBIROUFYLSSYDX-UHFFFAOYSA-M 0.000 claims description 8
- FXJNQQZSGLEFSR-UHFFFAOYSA-M benzyl-dimethyl-tetradecylazanium;chloride;hydrate Chemical compound O.[Cl-].CCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 FXJNQQZSGLEFSR-UHFFFAOYSA-M 0.000 claims description 8
- 239000002775 capsule Substances 0.000 claims description 8
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- 229920001577 copolymer Polymers 0.000 claims description 8
- 230000003111 delayed effect Effects 0.000 claims description 8
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 8
- 229920001983 poloxamer Polymers 0.000 claims description 8
- YJHSJERLYWNLQL-UHFFFAOYSA-N 2-hydroxyethyl(dimethyl)azanium;chloride Chemical compound Cl.CN(C)CCO YJHSJERLYWNLQL-UHFFFAOYSA-N 0.000 claims description 7
- 244000215068 Acacia senegal Species 0.000 claims description 7
- 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 claims description 7
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 7
- 229920000084 Gum arabic Polymers 0.000 claims description 7
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- 235000010489 acacia gum Nutrition 0.000 claims description 7
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- 235000010948 carboxy methyl cellulose Nutrition 0.000 claims description 7
- 239000008112 carboxymethyl-cellulose Substances 0.000 claims description 7
- 229960001927 cetylpyridinium chloride Drugs 0.000 claims description 7
- YMKDRGPMQRFJGP-UHFFFAOYSA-M cetylpyridinium chloride Chemical group [Cl-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 YMKDRGPMQRFJGP-UHFFFAOYSA-M 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
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- HICYUNOFRYFIMG-UHFFFAOYSA-N n,n-dimethyl-1-naphthalen-1-ylmethanamine;hydrochloride Chemical compound [Cl-].C1=CC=C2C(C[NH+](C)C)=CC=CC2=C1 HICYUNOFRYFIMG-UHFFFAOYSA-N 0.000 claims description 7
- 239000010452 phosphate Substances 0.000 claims description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 7
- 235000021317 phosphate Nutrition 0.000 claims description 7
- 230000000699 topical effect Effects 0.000 claims description 7
- CDOUZKKFHVEKRI-UHFFFAOYSA-N 3-bromo-n-[(prop-2-enoylamino)methyl]propanamide Chemical compound BrCCC(=O)NCNC(=O)C=C CDOUZKKFHVEKRI-UHFFFAOYSA-N 0.000 claims description 6
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 claims description 6
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- 125000000129 anionic group Chemical group 0.000 claims description 6
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 claims description 6
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- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 6
- GUBGYTABKSRVRQ-UHFFFAOYSA-N 2-(hydroxymethyl)-6-[4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxane-3,4,5-triol Chemical compound OCC1OC(OC2C(O)C(O)C(O)OC2CO)C(O)C(O)C1O GUBGYTABKSRVRQ-UHFFFAOYSA-N 0.000 claims description 5
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- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 5
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- DBRHJJQHHSOXCQ-UHFFFAOYSA-N 2,2-dihydroxyethyl(methyl)azanium;chloride Chemical compound [Cl-].C[NH2+]CC(O)O DBRHJJQHHSOXCQ-UHFFFAOYSA-N 0.000 claims description 4
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- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 claims description 4
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- BCOZLGOHQFNXBI-UHFFFAOYSA-M benzyl-bis(2-chloroethyl)-ethylazanium;bromide Chemical compound [Br-].ClCC[N+](CC)(CCCl)CC1=CC=CC=C1 BCOZLGOHQFNXBI-UHFFFAOYSA-M 0.000 claims description 4
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- WOQQAWHSKSSAGF-WXFJLFHKSA-N decyl beta-D-maltopyranoside Chemical compound O[C@@H]1[C@@H](O)[C@H](OCCCCCCCCCC)O[C@H](CO)[C@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 WOQQAWHSKSSAGF-WXFJLFHKSA-N 0.000 claims description 4
- JDRSMPFHFNXQRB-IBEHDNSVSA-N decyl glucoside Chemical compound CCCCCCCCCCO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O JDRSMPFHFNXQRB-IBEHDNSVSA-N 0.000 claims description 4
- CDJGWBCMWHSUHR-UHFFFAOYSA-M decyl(triethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCC[N+](CC)(CC)CC CDJGWBCMWHSUHR-UHFFFAOYSA-M 0.000 claims description 4
- PLMFYJJFUUUCRZ-UHFFFAOYSA-M decyltrimethylammonium bromide Chemical compound [Br-].CCCCCCCCCC[N+](C)(C)C PLMFYJJFUUUCRZ-UHFFFAOYSA-M 0.000 claims description 4
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Classifications
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- 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
- A61K9/145—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 compounds
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- 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
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- A—HUMAN NECESSITIES
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- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
- A61K9/2018—Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/2027—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
-
- 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
- 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
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Pulmonology (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US65825905P | 2005-03-03 | 2005-03-03 | |
| PCT/US2006/007465 WO2006096462A1 (en) | 2005-03-03 | 2006-03-02 | Nanoparticulate compositions of heterocyclic amide derivatives |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009045169A Division JP2009149679A (ja) | 2005-03-03 | 2009-02-27 | 複素環式アミド誘導体のナノ粒子状組成物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008531721A true JP2008531721A (ja) | 2008-08-14 |
| JP2008531721A5 JP2008531721A5 (enExample) | 2009-04-16 |
Family
ID=36953698
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007558231A Pending JP2008531721A (ja) | 2005-03-03 | 2006-03-02 | 複素環式アミド誘導体のナノ粒子状組成物 |
| JP2009045169A Pending JP2009149679A (ja) | 2005-03-03 | 2009-02-27 | 複素環式アミド誘導体のナノ粒子状組成物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009045169A Pending JP2009149679A (ja) | 2005-03-03 | 2009-02-27 | 複素環式アミド誘導体のナノ粒子状組成物 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20080254114A1 (enExample) |
| EP (1) | EP1855651A4 (enExample) |
| JP (2) | JP2008531721A (enExample) |
| CA (1) | CA2598288A1 (enExample) |
| WO (1) | WO2006096462A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012523427A (ja) * | 2009-04-09 | 2012-10-04 | アルカーメス ファーマ アイルランド リミテッド | 薬物送達組成物 |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2014233560B2 (en) * | 2009-04-09 | 2016-06-16 | Alkermes Pharma Ireland Limited | Drug delivery composition |
| US9012511B2 (en) | 2010-05-19 | 2015-04-21 | Alkermes Pharma Ireland Limited | Nanoparticulate cinacalcet compositions |
| US20140005269A1 (en) * | 2010-11-26 | 2014-01-02 | University Of The Witwatersrand, Johannesburg | Polymeric matrix of polymer-lipid nanoparticles as a pharmaceutical dosage form |
| JP2016522251A (ja) * | 2013-06-20 | 2016-07-28 | グレンマーク ファーマシューティカルズ, エセ.アー. | Trpa1アンタゴニストを含むナノ粒子製剤 |
| WO2015071841A1 (en) | 2013-11-12 | 2015-05-21 | Druggability Technologies Holdings Limited | Complexes of dabigatran and its derivatives, process for the preparation thereof and pharmaceutical compositions containing them |
| PT3174535T (pt) * | 2014-08-01 | 2019-05-27 | Glenmark Pharmaceuticals Sa | Formulação nanoparticulada compreendendo um inibidor de mpges-1 |
| PT109030B (pt) | 2015-12-15 | 2019-09-25 | Hovione Farmaciência, S.A. | Preparação de partículas inaláveis de zafirlucaste |
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-
2006
- 2006-03-02 JP JP2007558231A patent/JP2008531721A/ja active Pending
- 2006-03-02 CA CA002598288A patent/CA2598288A1/en not_active Abandoned
- 2006-03-02 US US11/571,377 patent/US20080254114A1/en not_active Abandoned
- 2006-03-02 WO PCT/US2006/007465 patent/WO2006096462A1/en not_active Ceased
- 2006-03-02 EP EP06736732A patent/EP1855651A4/en not_active Withdrawn
-
2009
- 2009-02-27 JP JP2009045169A patent/JP2009149679A/ja active Pending
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| JPH04266872A (ja) * | 1990-12-12 | 1992-09-22 | Imperial Chem Ind Plc <Ici> | 複素環式化合物 |
| JPH04295420A (ja) * | 1991-01-25 | 1992-10-20 | Sterling Winthrop Inc | 表面変性薬物微小粒子 |
| 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 |
| WO2004006959A1 (en) * | 2002-07-16 | 2004-01-22 | Elan Pharma International, Ltd | Liquid dosage compositions of stable nanoparticulate active agents |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012523427A (ja) * | 2009-04-09 | 2012-10-04 | アルカーメス ファーマ アイルランド リミテッド | 薬物送達組成物 |
| JP2015007111A (ja) * | 2009-04-09 | 2015-01-15 | アルカーメス ファーマ アイルランド リミテッド | 薬物送達組成物 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1855651A4 (en) | 2011-06-15 |
| JP2009149679A (ja) | 2009-07-09 |
| US20080254114A1 (en) | 2008-10-16 |
| WO2006096462A1 (en) | 2006-09-14 |
| EP1855651A1 (en) | 2007-11-21 |
| CA2598288A1 (en) | 2006-09-14 |
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