JP2005526785A5 - - Google Patents
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- JP2005526785A5 JP2005526785A5 JP2003577854A JP2003577854A JP2005526785A5 JP 2005526785 A5 JP2005526785 A5 JP 2005526785A5 JP 2003577854 A JP2003577854 A JP 2003577854A JP 2003577854 A JP2003577854 A JP 2003577854A JP 2005526785 A5 JP2005526785 A5 JP 2005526785A5
- Authority
- JP
- Japan
- Prior art keywords
- less
- chloride
- map kinase
- kinase inhibitor
- bromide
- 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.)
- Granted
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- 239000000203 mixture Substances 0.000 claims description 60
- 239000002829 mitogen activated protein kinase inhibitor Substances 0.000 claims description 47
- 229940122696 MAP kinase inhibitor Drugs 0.000 claims description 37
- 239000003381 stabilizer Substances 0.000 claims description 23
- 239000002245 particle Substances 0.000 claims description 19
- 239000002105 nanoparticle Substances 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 10
- 239000003112 inhibitor Substances 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 239000000032 diagnostic agent Substances 0.000 claims description 2
- 229940039227 diagnostic agent Drugs 0.000 claims description 2
- -1 Ioto-SB 203580 Chemical compound 0.000 claims 38
- 150000003839 salts Chemical class 0.000 claims 11
- 244000060011 Cocos nucifera Species 0.000 claims 10
- 235000013162 Cocos nucifera Nutrition 0.000 claims 10
- 102000043136 MAP kinase family Human genes 0.000 claims 10
- 108091054455 MAP kinase family Proteins 0.000 claims 10
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 claims 8
- 229940079593 drug Drugs 0.000 claims 8
- AISMNBXOJRHCIA-UHFFFAOYSA-N trimethylazanium;bromide Chemical compound Br.CN(C)C AISMNBXOJRHCIA-UHFFFAOYSA-N 0.000 claims 8
- 238000009472 formulation Methods 0.000 claims 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 6
- 108091000080 Phosphotransferase Proteins 0.000 claims 6
- 102000020233 phosphotransferase Human genes 0.000 claims 6
- 230000001105 regulatory effect Effects 0.000 claims 6
- 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 claims 5
- 108010068338 p38 Mitogen-Activated Protein Kinases Proteins 0.000 claims 5
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 claims 4
- DUQADSPERJRQBW-UHFFFAOYSA-N 2-[(3-hydroxy-4-nitrophenyl)methylidene]propanedinitrile Chemical compound OC1=CC(C=C(C#N)C#N)=CC=C1[N+]([O-])=O DUQADSPERJRQBW-UHFFFAOYSA-N 0.000 claims 4
- YJHSJERLYWNLQL-UHFFFAOYSA-N 2-hydroxyethyl(dimethyl)azanium;chloride Chemical compound Cl.CN(C)CCO YJHSJERLYWNLQL-UHFFFAOYSA-N 0.000 claims 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims 4
- 101001050288 Homo sapiens Transcription factor Jun Proteins 0.000 claims 4
- 108091034117 Oligonucleotide Proteins 0.000 claims 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims 4
- 102000001253 Protein Kinase Human genes 0.000 claims 4
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims 4
- 102100023132 Transcription factor Jun Human genes 0.000 claims 4
- 239000013543 active substance Substances 0.000 claims 4
- 150000001412 amines Chemical class 0.000 claims 4
- 229960000686 benzalkonium chloride Drugs 0.000 claims 4
- JBIROUFYLSSYDX-UHFFFAOYSA-M benzododecinium chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 JBIROUFYLSSYDX-UHFFFAOYSA-M 0.000 claims 4
- 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 4
- 229960001927 cetylpyridinium chloride Drugs 0.000 claims 4
- YMKDRGPMQRFJGP-UHFFFAOYSA-M cetylpyridinium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 YMKDRGPMQRFJGP-UHFFFAOYSA-M 0.000 claims 4
- 229940107161 cholesterol Drugs 0.000 claims 4
- 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 4
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 claims 4
- 229940043355 kinase inhibitor Drugs 0.000 claims 4
- 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 4
- GTVPOLSIJWJJNY-UHFFFAOYSA-N olomoucine Chemical compound N1=C(NCCO)N=C2N(C)C=NC2=C1NCC1=CC=CC=C1 GTVPOLSIJWJJNY-UHFFFAOYSA-N 0.000 claims 4
- 239000003757 phosphotransferase inhibitor Substances 0.000 claims 4
- 108060006633 protein kinase Proteins 0.000 claims 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 4
- 235000019333 sodium laurylsulphate Nutrition 0.000 claims 4
- 238000010521 absorption reaction Methods 0.000 claims 3
- 235000014113 dietary fatty acids Nutrition 0.000 claims 3
- 239000000194 fatty acid Substances 0.000 claims 3
- 229930195729 fatty acid Natural products 0.000 claims 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims 3
- 235000018102 proteins Nutrition 0.000 claims 3
- 102000004169 proteins and genes Human genes 0.000 claims 3
- 108090000623 proteins and genes Proteins 0.000 claims 3
- YKJYKKNCCRKFSL-RDBSUJKOSA-N (-)-anisomycin Chemical compound C1=CC(OC)=CC=C1C[C@@H]1[C@H](OC(C)=O)[C@@H](O)CN1 YKJYKKNCCRKFSL-RDBSUJKOSA-N 0.000 claims 2
- JVAZJLFFSJARQM-RMPHRYRLSA-N (2r,3r,4s,5s,6r)-2-hexoxy-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound CCCCCCO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O JVAZJLFFSJARQM-RMPHRYRLSA-N 0.000 claims 2
- QAQSNXHKHKONNS-UHFFFAOYSA-N 1-ethyl-2-hydroxy-4-methyl-6-oxopyridine-3-carboxamide Chemical compound CCN1C(O)=C(C(N)=O)C(C)=CC1=O QAQSNXHKHKONNS-UHFFFAOYSA-N 0.000 claims 2
- RMAJTXKOOKJAAV-UHFFFAOYSA-N 2,2-dihydroxyethyl(methyl)azanium;bromide Chemical compound [Br-].C[NH2+]CC(O)O RMAJTXKOOKJAAV-UHFFFAOYSA-N 0.000 claims 2
- DBRHJJQHHSOXCQ-UHFFFAOYSA-N 2,2-dihydroxyethyl(methyl)azanium;chloride Chemical compound [Cl-].C[NH2+]CC(O)O DBRHJJQHHSOXCQ-UHFFFAOYSA-N 0.000 claims 2
- BSTPEQSVYGELTA-UHFFFAOYSA-N 2-(dimethylamino)ethanol;hydrobromide Chemical compound [Br-].C[NH+](C)CCO BSTPEQSVYGELTA-UHFFFAOYSA-N 0.000 claims 2
- MPNXSZJPSVBLHP-UHFFFAOYSA-N 2-chloro-n-phenylpyridine-3-carboxamide Chemical compound ClC1=NC=CC=C1C(=O)NC1=CC=CC=C1 MPNXSZJPSVBLHP-UHFFFAOYSA-N 0.000 claims 2
- BZSJQMAZLOWECR-UHFFFAOYSA-N 2-methylprop-2-enoate trimethylazanium bromide Chemical compound [Br-].C[NH+](C)C.C(C(=C)C)(=O)[O-].C[NH+](C)C BZSJQMAZLOWECR-UHFFFAOYSA-N 0.000 claims 2
- XEOVWJYINDYNSM-UHFFFAOYSA-N 4-[4-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)-1H-imidazol-5-yl]pyridine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=NC(C=2C=CC(F)=CC=2)=C(C=2C=CN=CC=2)N1 XEOVWJYINDYNSM-UHFFFAOYSA-N 0.000 claims 2
- XOQSUTIMRLPFPB-UHFFFAOYSA-N 4-[4-(4-fluorophenyl)-5-pyridin-4-yl-1H-imidazol-2-yl]phenol hydrochloride Chemical compound Cl.C1=CC(O)=CC=C1C1=NC(C=2C=CC(F)=CC=2)=C(C=2C=CN=CC=2)N1 XOQSUTIMRLPFPB-UHFFFAOYSA-N 0.000 claims 2
- YOELZIQOLWZLQC-UHFFFAOYSA-N 6-(4-fluorophenyl)-5-pyridin-4-yl-2,3-dihydroimidazo[2,1-b]thiazole Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=CN=CC=2)N2CCSC2=N1 YOELZIQOLWZLQC-UHFFFAOYSA-N 0.000 claims 2
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 claims 2
- YKJYKKNCCRKFSL-UHFFFAOYSA-N Anisomycin Natural products C1=CC(OC)=CC=C1CC1C(OC(C)=O)C(O)CN1 YKJYKKNCCRKFSL-UHFFFAOYSA-N 0.000 claims 2
- 241000416162 Astragalus gummifer Species 0.000 claims 2
- CXRFDZFCGOPDTD-UHFFFAOYSA-M Cetrimide Chemical compound [Br-].CCCCCCCCCCCCCC[N+](C)(C)C CXRFDZFCGOPDTD-UHFFFAOYSA-M 0.000 claims 2
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 claims 2
- 244000303965 Cyamopsis psoralioides Species 0.000 claims 2
- 229920002307 Dextran Polymers 0.000 claims 2
- RUPBZQFQVRMKDG-UHFFFAOYSA-M Didecyldimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCC[N+](C)(C)CCCCCCCCCC RUPBZQFQVRMKDG-UHFFFAOYSA-M 0.000 claims 2
- 108700022174 Drosophila Son of Sevenless Proteins 0.000 claims 2
- 102100023274 Dual specificity mitogen-activated protein kinase kinase 4 Human genes 0.000 claims 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims 2
- 102100029974 GTPase HRas Human genes 0.000 claims 2
- 101710091881 GTPase HRas Proteins 0.000 claims 2
- 108010010803 Gelatin Proteins 0.000 claims 2
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 claims 2
- 102100033067 Growth factor receptor-bound protein 2 Human genes 0.000 claims 2
- 229920000084 Gum arabic Polymers 0.000 claims 2
- 101000871017 Homo sapiens Growth factor receptor-bound protein 2 Proteins 0.000 claims 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 claims 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 claims 2
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims 2
- 108040006417 JUN kinase kinase activity proteins Proteins 0.000 claims 2
- 102000001291 MAP Kinase Kinase Kinase Human genes 0.000 claims 2
- 108060006687 MAP kinase kinase kinase Proteins 0.000 claims 2
- 108010041955 MAP-kinase-activated kinase 2 Proteins 0.000 claims 2
- 102000016943 Muramidase Human genes 0.000 claims 2
- 108010014251 Muramidase Proteins 0.000 claims 2
- 108010062010 N-Acetylmuramoyl-L-alanine Amidase Proteins 0.000 claims 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims 2
- JVAZJLFFSJARQM-UHFFFAOYSA-N O-n-hexyl beta-D-glucopyranoside Natural products CCCCCCOC1OC(CO)C(O)C(O)C1O JVAZJLFFSJARQM-UHFFFAOYSA-N 0.000 claims 2
- 229910019142 PO4 Inorganic materials 0.000 claims 2
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 claims 2
- 239000002202 Polyethylene glycol Substances 0.000 claims 2
- 239000004721 Polyphenylene oxide Substances 0.000 claims 2
- 229920001214 Polysorbate 60 Polymers 0.000 claims 2
- 239000004372 Polyvinyl alcohol Substances 0.000 claims 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 2
- 235000021355 Stearic acid Nutrition 0.000 claims 2
- 229920001615 Tragacanth Polymers 0.000 claims 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims 2
- 229930003427 Vitamin E Natural products 0.000 claims 2
- NJSSICCENMLTKO-HRCBOCMUSA-N [(1r,2s,4r,5r)-3-hydroxy-4-(4-methylphenyl)sulfonyloxy-6,8-dioxabicyclo[3.2.1]octan-2-yl] 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)O[C@H]1C(O)[C@@H](OS(=O)(=O)C=2C=CC(C)=CC=2)[C@@H]2OC[C@H]1O2 NJSSICCENMLTKO-HRCBOCMUSA-N 0.000 claims 2
- FOLJTMYCYXSPFQ-CJKAUBRRSA-N [(2r,3s,4s,5r,6r)-6-[(2s,3s,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)-2-(octadecanoyloxymethyl)oxolan-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl octadecanoate Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](COC(=O)CCCCCCCCCCCCCCCCC)O[C@@H]1O[C@@]1(COC(=O)CCCCCCCCCCCCCCCCC)[C@@H](O)[C@H](O)[C@@H](CO)O1 FOLJTMYCYXSPFQ-CJKAUBRRSA-N 0.000 claims 2
- SZYSLWCAWVWFLT-UTGHZIEOSA-N [(2s,3s,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)-2-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxolan-2-yl]methyl octadecanoate Chemical compound O([C@@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@]1(COC(=O)CCCCCCCCCCCCCCCCC)O[C@H](CO)[C@@H](O)[C@@H]1O SZYSLWCAWVWFLT-UTGHZIEOSA-N 0.000 claims 2
- GBSORQPIBBOORR-UHFFFAOYSA-N [Cl-].[Br-].C[NH+](C)CCO.C[NH+](C)CCO Chemical compound [Cl-].[Br-].C[NH+](C)CCO.C[NH+](C)CCO GBSORQPIBBOORR-UHFFFAOYSA-N 0.000 claims 2
- 239000000205 acacia gum Substances 0.000 claims 2
- 235000010489 acacia gum Nutrition 0.000 claims 2
- 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 2
- 150000003926 acrylamides Chemical group 0.000 claims 2
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 claims 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims 2
- 125000006177 alkyl benzyl group Chemical group 0.000 claims 2
- 150000005215 alkyl ethers Chemical class 0.000 claims 2
- 125000005211 alkyl trimethyl ammonium group Chemical group 0.000 claims 2
- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 claims 2
- 235000001014 amino acid Nutrition 0.000 claims 2
- 150000001413 amino acids Chemical class 0.000 claims 2
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 claims 2
- 235000019270 ammonium chloride Nutrition 0.000 claims 2
- 239000000730 antalgic agent Substances 0.000 claims 2
- 229940041181 antineoplastic drug Drugs 0.000 claims 2
- 239000000074 antisense oligonucleotide Substances 0.000 claims 2
- 238000012230 antisense oligonucleotides Methods 0.000 claims 2
- XADJWCRESPGUTB-UHFFFAOYSA-N apigenin Natural products C1=CC(O)=CC=C1C1=CC(=O)C2=CC(O)=C(O)C=C2O1 XADJWCRESPGUTB-UHFFFAOYSA-N 0.000 claims 2
- KZNIFHPLKGYRTM-UHFFFAOYSA-N apigenin Chemical compound C1=CC(O)=CC=C1C1=CC(=O)C2=C(O)C=C(O)C=C2O1 KZNIFHPLKGYRTM-UHFFFAOYSA-N 0.000 claims 2
- 229940117893 apigenin Drugs 0.000 claims 2
- 235000008714 apigenin Nutrition 0.000 claims 2
- KHSLHYAUZSPBIU-UHFFFAOYSA-M benzododecinium bromide Chemical compound [Br-].CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 KHSLHYAUZSPBIU-UHFFFAOYSA-M 0.000 claims 2
- UUZYBYIOAZTMGC-UHFFFAOYSA-M benzyl(trimethyl)azanium;bromide Chemical compound [Br-].C[N+](C)(C)CC1=CC=CC=C1 UUZYBYIOAZTMGC-UHFFFAOYSA-M 0.000 claims 2
- 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 2
- WMLFGKCFDKMAKB-UHFFFAOYSA-M benzyl-diethyl-tetradecylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[N+](CC)(CC)CC1=CC=CC=C1 WMLFGKCFDKMAKB-UHFFFAOYSA-M 0.000 claims 2
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 claims 2
- 239000008116 calcium stearate Substances 0.000 claims 2
- 235000013539 calcium stearate Nutrition 0.000 claims 2
- 229940078456 calcium stearate Drugs 0.000 claims 2
- 239000001768 carboxy methyl cellulose Substances 0.000 claims 2
- 229940084030 carboxymethylcellulose calcium Drugs 0.000 claims 2
- 239000005018 casein Substances 0.000 claims 2
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 claims 2
- 235000021240 caseins Nutrition 0.000 claims 2
- 239000004359 castor oil Substances 0.000 claims 2
- 235000019438 castor oil Nutrition 0.000 claims 2
- 150000001768 cations Chemical class 0.000 claims 2
- 229920002678 cellulose Polymers 0.000 claims 2
- 239000001913 cellulose Substances 0.000 claims 2
- 229940082500 cetostearyl alcohol Drugs 0.000 claims 2
- 235000012000 cholesterol Nutrition 0.000 claims 2
- 229940075614 colloidal silicon dioxide Drugs 0.000 claims 2
- 230000000052 comparative effect Effects 0.000 claims 2
- 238000013270 controlled release Methods 0.000 claims 2
- 239000003246 corticosteroid Substances 0.000 claims 2
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- 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 2
- CDJGWBCMWHSUHR-UHFFFAOYSA-M decyl(triethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCC[N+](CC)(CC)CC CDJGWBCMWHSUHR-UHFFFAOYSA-M 0.000 claims 2
- GFNWBSUGVDMEQI-UHFFFAOYSA-L decyl-(2-hydroxyethyl)-dimethylazanium;bromide;chloride Chemical compound [Cl-].[Br-].CCCCCCCCCC[N+](C)(C)CCO.CCCCCCCCCC[N+](C)(C)CCO GFNWBSUGVDMEQI-UHFFFAOYSA-L 0.000 claims 2
- RLGGVUPWOJOQHP-UHFFFAOYSA-M decyl-(2-hydroxyethyl)-dimethylazanium;chloride Chemical compound [Cl-].CCCCCCCCCC[N+](C)(C)CCO RLGGVUPWOJOQHP-UHFFFAOYSA-M 0.000 claims 2
- PLMFYJJFUUUCRZ-UHFFFAOYSA-M decyltrimethylammonium bromide Chemical compound [Br-].CCCCCCCCCC[N+](C)(C)C PLMFYJJFUUUCRZ-UHFFFAOYSA-M 0.000 claims 2
- 229960004670 didecyldimethylammonium chloride Drugs 0.000 claims 2
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical class Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 claims 2
- JMGZBMRVDHKMKB-UHFFFAOYSA-L disodium;2-sulfobutanedioate Chemical compound [Na+].[Na+].OS(=O)(=O)C(C([O-])=O)CC([O-])=O JMGZBMRVDHKMKB-UHFFFAOYSA-L 0.000 claims 2
- 229960000878 docusate sodium Drugs 0.000 claims 2
- NLEBIOOXCVAHBD-QKMCSOCLSA-N dodecyl beta-D-maltoside Chemical compound O[C@@H]1[C@@H](O)[C@H](OCCCCCCCCCCCC)O[C@H](CO)[C@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 NLEBIOOXCVAHBD-QKMCSOCLSA-N 0.000 claims 2
- VVNBOKHXEBSBQJ-UHFFFAOYSA-M dodecyl(triethyl)azanium;bromide Chemical compound [Br-].CCCCCCCCCCCC[N+](CC)(CC)CC VVNBOKHXEBSBQJ-UHFFFAOYSA-M 0.000 claims 2
- XJWSAJYUBXQQDR-UHFFFAOYSA-M dodecyltrimethylammonium bromide Chemical compound [Br-].CCCCCCCCCCCC[N+](C)(C)C XJWSAJYUBXQQDR-UHFFFAOYSA-M 0.000 claims 2
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| US36552402P | 2002-03-20 | 2002-03-20 | |
| PCT/US2003/008547 WO2003080024A2 (en) | 2002-03-20 | 2003-03-20 | Nanoparticulate compositions of map kinase inhibitors |
Related Child Applications (1)
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| JP2010168818A Division JP2010280685A (ja) | 2002-03-20 | 2010-07-28 | Ｍａｐキナーゼ阻害剤のナノ粒子組成物 |
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| DE (1) | DE60319073T2 (https=) |
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| US20020119237A1 (en) * | 2000-12-22 | 2002-08-29 | Hevey Maurice O. | Medium and method for delivery of edible materials subject to degradation by oxidation and hydrolysis |
| EP1471887B1 (en) | 2002-02-04 | 2010-04-21 | Elan Pharma International Ltd. | Nanoparticulate compositions having lysozyme as a surface stabilizer |
| AU2003300076C1 (en) | 2002-12-30 | 2010-03-04 | Angiotech International Ag | Drug delivery from rapid gelling polymer composition |
| US20080045706A1 (en) * | 2002-12-31 | 2008-02-21 | Flynn Daniel L | Anti-inflammatory medicaments |
| US7279576B2 (en) * | 2002-12-31 | 2007-10-09 | Deciphera Pharmaceuticals, Llc | Anti-cancer medicaments |
| US7144911B2 (en) | 2002-12-31 | 2006-12-05 | Deciphera Pharmaceuticals Llc | Anti-inflammatory medicaments |
| US7202257B2 (en) * | 2003-12-24 | 2007-04-10 | Deciphera Pharmaceuticals, Llc | Anti-inflammatory medicaments |
| US20040248982A1 (en) * | 2003-06-09 | 2004-12-09 | Dyer Gordon Wayne | Use of compounds for the inhibition of proteins and UV protection |
| ATE415946T1 (de) * | 2003-08-08 | 2008-12-15 | Elan Pharma Int Ltd | Neue metaxalon-zusammensetzungen |
| EP1686962B9 (en) | 2003-11-05 | 2012-10-03 | Elan Pharma International Limited | Nanoparticulate compositions having a peptide as a surface stabilizer |
| US7109163B2 (en) * | 2004-01-30 | 2006-09-19 | Ethicon, Inc. | Hemostatic compositions and devices |
| WO2006007520A1 (en) * | 2004-07-01 | 2006-01-19 | Wisconsin Alumni Research Foundation | Hydroxybenazamide compounds for treatment of cancer |
| JP2007223903A (ja) * | 2004-07-09 | 2007-09-06 | Takeda Chem Ind Ltd | 新規な固体分散体およびその製造方法 |
| AU2006235487B2 (en) | 2005-04-12 | 2011-12-22 | Elan Pharma International Limited | Nanoparticulate quinazoline derivative formulations |
| JP2008540546A (ja) * | 2005-05-10 | 2008-11-20 | エラン ファーマ インターナショナル リミテッド | ナノ粒子クロピドグレル製剤 |
| US20110064803A1 (en) * | 2005-05-10 | 2011-03-17 | Elan Pharma International Limited. | Nanoparticulate and controlled release compositions comprising vitamin k2 |
| CN101262860A (zh) * | 2005-06-03 | 2008-09-10 | 伊兰制药国际有限公司 | 纳米微粒对乙酰氨基酚制剂 |
| EA015102B1 (ru) * | 2005-06-03 | 2011-06-30 | Элан Фарма Интернэшнл Лтд. | Препараты наночастиц мезилата иматиниба |
| WO2006133045A1 (en) * | 2005-06-03 | 2006-12-14 | Elan Pharma International, Limited | Nanoparticulate benidipine compositions |
| WO2008073068A1 (en) | 2005-06-08 | 2008-06-19 | Elan Pharma International Limited | Nanoparticulate and controlled release compositions comprising cefditoren |
| ES2335608T3 (es) * | 2005-06-09 | 2010-03-30 | Elan Pharma International Limited | Formulaciones de ebistina nanoparticuladas. |
| MX2007015882A (es) * | 2005-06-13 | 2008-03-04 | Elan Pharma Int Ltd | Formulaciones en combinacion nanoparticulada de clopidogrel y aspirina. |
| CA2612384A1 (en) * | 2005-06-15 | 2006-12-28 | Elan Pharma International, Limited | Nanoparticulate azelnidipine formulations |
| JP2009500356A (ja) * | 2005-07-07 | 2009-01-08 | エラン ファーマ インターナショナル リミテッド | ナノ粒子クラリスロマイシン製剤 |
| JP2009507925A (ja) * | 2005-09-13 | 2009-02-26 | エラン ファーマ インターナショナル リミテッド | ナノ粒子タダラフィル製剤 |
| CA2622758A1 (en) | 2005-09-15 | 2007-03-29 | Elan Pharma International, Limited | Nanoparticulate aripiprazole formulations |
| SG170047A1 (en) | 2006-05-30 | 2011-04-29 | Elan Pharma Int Ltd | Nanoparticulate posaconazole formulations |
| KR20090018864A (ko) * | 2006-06-13 | 2009-02-23 | 엘란 파마 인터내셔널 리미티드 | 나노입자형 키나제 억제제 제제 |
| AU2007272501A1 (en) * | 2006-07-12 | 2008-01-17 | Elan Pharma International Limited | Nanoparticulate formulations of modafinil |
| AU2008215659B2 (en) * | 2007-02-16 | 2012-11-01 | Aska Pharmaceutical Co., Ltd. | Pharmaceutical composition comprising microparticle oily suspension |
| EP2152274A4 (en) * | 2007-05-07 | 2010-07-21 | Questor Pharmaceuticals Inc | NASAL ADMINISTRATION OF BENZODIAZEPINES |
| US8530463B2 (en) * | 2007-05-07 | 2013-09-10 | Hale Biopharma Ventures Llc | Multimodal particulate formulations |
| AU2009225719A1 (en) * | 2008-03-21 | 2009-09-24 | Elan Pharma International Limited | Compositions for site-specific delivery of imatinib and methods of use |
| US20090258865A1 (en) | 2008-03-28 | 2009-10-15 | Hale Biopharma Ventures, Llc | Administration of benzodiazepine compositions |
| US8110608B2 (en) | 2008-06-05 | 2012-02-07 | Ecolab Usa Inc. | Solid form sodium lauryl sulfate (SLS) pesticide composition |
| EP2172193A1 (en) | 2008-10-02 | 2010-04-07 | Capsulution Nanoscience AG | Improved nanoparticulate compositions of poorly soluble compounds |
| EP3167875A1 (en) | 2009-05-27 | 2017-05-17 | Alkermes Pharma Ireland Limited | Reduction of flake-like aggregation in nanoparticulate meloxicam compositions |
| TR200904500A2 (tr) | 2009-06-10 | 2009-10-21 | Öner Levent | Ezetimib nanokristallerinin hazırlanması için yöntem ve farmasötik formülasyonları. |
| US8637569B2 (en) | 2009-10-22 | 2014-01-28 | Api Genesis, Llc | Methods of increasing solubility of poorly soluble compounds and methods of making and using formulations of such compounds |
| WO2011049629A2 (en) | 2009-10-22 | 2011-04-28 | Api Genesis, Llc | Methods of making and using compositions comprising flavonoids |
| US8968757B2 (en) | 2010-10-12 | 2015-03-03 | Ecolab Usa Inc. | Highly wettable, water dispersible, granules including two pesticides |
| ES2683902T3 (es) | 2011-06-14 | 2018-09-28 | Hale Biopharma Ventures, Llc | Administración de benzodiacepina |
| KR101794032B1 (ko) * | 2011-09-21 | 2017-11-07 | (주)바이오시네틱스 | 나노입자 제조방법 |
| IL315294A (en) | 2015-03-03 | 2024-10-01 | Pharmacyclics Llc | Pharmaceutical formulations of bruton's tyrosine kinase inhibitor |
| WO2017075013A1 (en) * | 2015-10-26 | 2017-05-04 | Eip Pharma, Llc | Methods and compositions for recovery from stroke |
| US11466008B2 (en) | 2017-09-18 | 2022-10-11 | Eip Pharma, Llc | Co-crystals of neflamapimod (VX-745) |
| JP2020152673A (ja) | 2019-03-20 | 2020-09-24 | 株式会社リコー | ナノ粒子及びナノ粒子の製造方法、並びに医薬 |
| EP3991750A4 (en) * | 2019-06-26 | 2022-08-03 | Ricoh Company, Ltd. | PHARMACEUTICAL COMPOSITION |
| JP2024521399A (ja) | 2021-06-10 | 2024-05-31 | ニューレリス、インク． | 小児患者における発作性障害を治療するための組成物および方法 |
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| FR2608988B1 (fr) * | 1986-12-31 | 1991-01-11 | Centre Nat Rech Scient | Procede de preparation de systemes colloidaux dispersibles d'une substance, sous forme de nanoparticules |
| US5145684A (en) * | 1991-01-25 | 1992-09-08 | Sterling Drug Inc. | Surface modified drug nanoparticles |
| US5834025A (en) * | 1995-09-29 | 1998-11-10 | Nanosystems L.L.C. | Reduction of intravenously administered nanoparticulate-formulation-induced adverse physiological reactions |
| JP4107693B2 (ja) * | 1996-02-09 | 2008-06-25 | 保土谷化学工業株式会社 | 固体粒子水性懸濁液の製造方法 |
| US6361938B1 (en) * | 1996-11-08 | 2002-03-26 | Elan Corporation, Plc | Peptides which enhance transport across tissues and methods of identifying and using the same |
| WO2000012124A1 (en) * | 1998-09-01 | 2000-03-09 | Elan Corporation, Plc | Oral vaccine compositions |
| EP2266542A3 (en) * | 1998-10-01 | 2013-07-31 | Elan Pharma International Limited | Controlled release nanoparticulate compositions |
| EP1261334A1 (en) * | 1998-10-20 | 2002-12-04 | Omeros Corporation | Irrigation solution containing mapk inhibitors and their use for treating pain and inflammation |
| US6375986B1 (en) * | 2000-09-21 | 2002-04-23 | Elan Pharma International Ltd. | Solid dose nanoparticulate compositions comprising a synergistic combination of a polymeric surface stabilizer and dioctyl sodium sulfosuccinate |
| US6656504B1 (en) * | 1999-09-09 | 2003-12-02 | Elan Pharma International Ltd. | Nanoparticulate compositions comprising amorphous cyclosporine and methods of making and using such compositions |
| BR0014041A (pt) * | 1999-09-17 | 2003-07-15 | Smithkline Beecham Corp | Utilização de csaids em infecção por rinovìrus |
-
2003
- 2003-03-20 EP EP03723782A patent/EP1490025B1/en not_active Expired - Lifetime
- 2003-03-20 ES ES03723782T patent/ES2302925T3/es not_active Expired - Lifetime
- 2003-03-20 WO PCT/US2003/008547 patent/WO2003080024A2/en not_active Ceased
- 2003-03-20 AU AU2003230692A patent/AU2003230692A1/en not_active Abandoned
- 2003-03-20 CA CA2479737A patent/CA2479737C/en not_active Expired - Fee Related
- 2003-03-20 DE DE60319073T patent/DE60319073T2/de not_active Expired - Lifetime
- 2003-03-20 AT AT03723782T patent/ATE385777T1/de not_active IP Right Cessation
- 2003-03-20 JP JP2003577854A patent/JP4611641B2/ja not_active Expired - Fee Related
- 2003-03-20 US US10/392,303 patent/US20030181411A1/en not_active Abandoned
-
2010
- 2010-07-28 JP JP2010168818A patent/JP2010280685A/ja active Pending
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