IL173743A - Oral preparations containing itraconazole and their preparation - Google Patents

Oral preparations containing itraconazole and their preparation

Info

Publication number: IL173743A
Authority: IL; Israel
Prior art keywords: composition; itraconazole; surfactant; preparation; mixture
Prior art date: 2003-09-09

Application number

IL173743A

Other languages

English (en)

Hebrew (he)

Other versions

IL173743A0 (en

Original Assignee

Hanmi Pharm Ind Co Ltd

Priority date (The priority date 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 date listed.)

2003-09-09

Filing date

2006-02-15

Publication date

2012-08-30

2004-09-07 Priority claimed from PCT/KR2004/002264 external-priority patent/WO2005023262A1/fr

2006-02-15 Application filed by Hanmi Pharm Ind Co Ltd filed Critical Hanmi Pharm Ind Co Ltd

2006-07-05 Publication of IL173743A0 publication Critical patent/IL173743A0/en

2012-08-30 Publication of IL173743A publication Critical patent/IL173743A/en

Links

239000000203 mixture Substances 0.000 title claims description 66
VHVPQPYKVGDNFY-DFMJLFEVSA-N 2-[(2r)-butan-2-yl]-4-[4-[4-[4-[[(2r,4s)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-1,2,4-triazol-3-one Chemical compound O=C1N([C@H](C)CC)N=CN1C1=CC=C(N2CCN(CC2)C=2C=CC(OC[C@@H]3O[C@](CN4N=CN=C4)(OC3)C=3C(=CC(Cl)=CC=3)Cl)=CC=2)C=C1 VHVPQPYKVGDNFY-DFMJLFEVSA-N 0.000 title claims description 62
229960004130 itraconazole Drugs 0.000 title claims description 62
238000002360 preparation method Methods 0.000 title description 37
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 50
238000000034 method Methods 0.000 claims description 27
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 22
239000002904 solvent Substances 0.000 claims description 16
239000000654 additive Substances 0.000 claims description 15
XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 claims description 15
239000004094 surface-active agent Substances 0.000 claims description 15
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 description 14
239000003921 oil Substances 0.000 claims description 14
235000019198 oils Nutrition 0.000 claims description 14
230000000996 additive effect Effects 0.000 claims description 13
-1 polyoxyethylene Polymers 0.000 claims description 12
239000002535 acidifier Substances 0.000 claims description 11
235000013305 food Nutrition 0.000 claims description 11
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
230000037406 food intake Effects 0.000 claims description 8
239000000243 solution Substances 0.000 claims description 8
239000004530 micro-emulsion Substances 0.000 claims description 6
229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 5
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 5
239000000194 fatty acid Substances 0.000 claims description 5
MEJYDZQQVZJMPP-ULAWRXDQSA-N (3s,3ar,6r,6ar)-3,6-dimethoxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan Chemical compound CO[C@H]1CO[C@@H]2[C@H](OC)CO[C@@H]21 MEJYDZQQVZJMPP-ULAWRXDQSA-N 0.000 claims description 4
235000014113 dietary fatty acids Nutrition 0.000 claims description 3
229930195729 fatty acid Natural products 0.000 claims description 3
CTPDSKVQLSDPLC-UHFFFAOYSA-N 2-(oxolan-2-ylmethoxy)ethanol Chemical compound OCCOCC1CCCO1 CTPDSKVQLSDPLC-UHFFFAOYSA-N 0.000 claims description 2
239000007864 aqueous solution Substances 0.000 claims description 2
210000001124 body fluid Anatomy 0.000 claims description 2
239000010839 body fluid Substances 0.000 claims description 2
239000008172 hydrogenated vegetable oil Substances 0.000 claims description 2
239000002245 particle Substances 0.000 claims description 2
RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims description 2
229930003799 tocopherol Natural products 0.000 claims description 2
239000011732 tocopherol Substances 0.000 claims description 2
229960001295 tocopherol Drugs 0.000 claims 1
235000010384 tocopherol Nutrition 0.000 claims 1
GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 claims 1
239000007902 hard capsule Substances 0.000 description 26
239000002775 capsule Substances 0.000 description 16
239000004615 ingredient Substances 0.000 description 15
235000001815 DL-alpha-tocopherol Nutrition 0.000 description 13
239000011627 DL-alpha-tocopherol Substances 0.000 description 13
239000008389 polyethoxylated castor oil Substances 0.000 description 13
239000004359 castor oil Substances 0.000 description 12
235000019438 castor oil Nutrition 0.000 description 12
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 12
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
238000004090 dissolution Methods 0.000 description 7
239000007788 liquid Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
230000000052 comparative effect Effects 0.000 description 6
VHVPQPYKVGDNFY-ZPGVKDDISA-N itraconazole Chemical compound O=C1N(C(C)CC)N=CN1C1=CC=C(N2CCN(CC2)C=2C=CC(OC[C@@H]3O[C@](CN4N=CN=C4)(OC3)C=3C(=CC(Cl)=CC=3)Cl)=CC=2)C=C1 VHVPQPYKVGDNFY-ZPGVKDDISA-N 0.000 description 6
229940063138 sporanox Drugs 0.000 description 6
238000012360 testing method Methods 0.000 description 6
241000700159 Rattus Species 0.000 description 5
239000011324 bead Substances 0.000 description 5
210000004369 blood Anatomy 0.000 description 5
239000008280 blood Substances 0.000 description 5
238000004519 manufacturing process Methods 0.000 description 5
239000008194 pharmaceutical composition Substances 0.000 description 5
230000007935 neutral effect Effects 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
229920000858 Cyclodextrin Polymers 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
210000004051 gastric juice Anatomy 0.000 description 3
239000008187 granular material Substances 0.000 description 3
238000001727 in vivo Methods 0.000 description 3
229920000136 polysorbate Polymers 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000007901 soft capsule Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000007962 solid dispersion Substances 0.000 description 3
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
238000007922 dissolution test Methods 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
238000011049 filling Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
IPCSVZSSVZVIGE-UHFFFAOYSA-N n-hexadecanoic acid Natural products CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
239000008363 phosphate buffer Substances 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 2
229960002920 sorbitol Drugs 0.000 description 2
239000012085 test solution Substances 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
229920003169 water-soluble polymer Polymers 0.000 description 2
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
LEZWWPYKPKIXLL-UHFFFAOYSA-N 1-{2-(4-chlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl}imidazole Chemical compound C1=CC(Cl)=CC=C1COC(C=1C(=CC(Cl)=CC=1)Cl)CN1C=NC=C1 LEZWWPYKPKIXLL-UHFFFAOYSA-N 0.000 description 1
RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 1
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 description 1
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
IELOKBJPULMYRW-NJQVLOCASA-N D-alpha-Tocopheryl Acid Succinate Chemical compound OC(=O)CCC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C IELOKBJPULMYRW-NJQVLOCASA-N 0.000 description 1
ZAKOWWREFLAJOT-CEFNRUSXSA-N D-alpha-tocopherylacetate Chemical compound CC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-CEFNRUSXSA-N 0.000 description 1
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
229920001353 Dextrin Polymers 0.000 description 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
SHBUUTHKGIVMJT-UHFFFAOYSA-N Hydroxystearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OO SHBUUTHKGIVMJT-UHFFFAOYSA-N 0.000 description 1
208000031888 Mycoses Diseases 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
239000005642 Oleic acid Substances 0.000 description 1
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
235000021314 Palmitic acid Nutrition 0.000 description 1
229920002685 Polyoxyl 35CastorOil Polymers 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
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 description 1
AOBORMOPSGHCAX-UHFFFAOYSA-N Tocophersolan Chemical compound OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-UHFFFAOYSA-N 0.000 description 1
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 1
239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
239000002253 acid Substances 0.000 description 1
238000005054 agglomeration Methods 0.000 description 1
230000002776 aggregation Effects 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
230000000843 anti-fungal effect Effects 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
235000006708 antioxidants Nutrition 0.000 description 1
239000003443 antiviral agent Substances 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
230000037396 body weight Effects 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
230000001186 cumulative effect Effects 0.000 description 1
ZAKOWWREFLAJOT-UHFFFAOYSA-N d-alpha-Tocopheryl acetate Natural products CC(=O)OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-UHFFFAOYSA-N 0.000 description 1
FYGDTMLNYKFZSV-MRCIVHHJSA-N dextrin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)OC1O[C@@H]1[C@@H](CO)OC(O[C@@H]2[C@H](O[C@H](O)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FYGDTMLNYKFZSV-MRCIVHHJSA-N 0.000 description 1
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
229960003913 econazole Drugs 0.000 description 1
ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 description 1
210000003238 esophagus Anatomy 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001125 extrusion Methods 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
235000011389 fruit/vegetable juice Nutrition 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
FOYKKGHVWRFIBD-UHFFFAOYSA-N gamma-tocopherol acetate Natural products CC(=O)OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 FOYKKGHVWRFIBD-UHFFFAOYSA-N 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
238000012812 general test Methods 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
229920001477 hydrophilic polymer Polymers 0.000 description 1
229940072106 hydroxystearate Drugs 0.000 description 1
230000000968 intestinal effect Effects 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
229960003511 macrogol Drugs 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
POULHZVOKOAJMA-UHFFFAOYSA-N methyl undecanoic acid Natural products CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 1
239000011259 mixed solution Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
235000021313 oleic acid Nutrition 0.000 description 1
229920000620 organic polymer Polymers 0.000 description 1
239000003960 organic solvent Substances 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
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000012545 processing Methods 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
239000008213 purified water Substances 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000012086 standard solution Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
235000019149 tocopherols Nutrition 0.000 description 1
238000005303 weighing Methods 0.000 description 1
QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 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
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
- 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
- A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
- 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
- A61K9/485—Inorganic compounds

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
Epidemiology (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Inorganic Chemistry (AREA)
Biophysics (AREA)
Molecular Biology (AREA)
Dispersion Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicinal Preparation (AREA)
Plural Heterocyclic Compounds (AREA)

IL173743A 2003-09-09 2006-02-15 Oral preparations containing itraconazole and their preparation IL173743A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
KR10-2003-0063147A KR100529766B1 (ko)	2003-09-09	2003-09-09	음식물 섭취에 따른 영향이 적은, 이트라코나졸경구투여용 조성물 및 이의 제조 방법
PCT/KR2004/002264 WO2005023262A1 (fr)	2003-09-09	2004-09-07	Composition orale d'itraconazole non affectee par la nourriture ingere et son procede de preparation

Publications (2)

Publication Number	Publication Date
IL173743A0 IL173743A0 (en)	2006-07-05
IL173743A true IL173743A (en)	2012-08-30

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Application Number	Title	Priority Date	Filing Date
IL173743A IL173743A (en)	2003-09-09	2006-02-15	Oral preparations containing itraconazole and their preparation

Country Status (10)

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EP (1)	EP1663231A4 (fr)
JP (1)	JP2007505103A (fr)
KR (1)	KR100529766B1 (fr)
CN (1)	CN100475211C (fr)
AU (1)	AU2004270069B2 (fr)
BR (1)	BRPI0414192A (fr)
CA (1)	CA2538019C (fr)
IL (1)	IL173743A (fr)
MX (1)	MXPA06002239A (fr)
RU (1)	RU2006111477A (fr)

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KR20200065093A (ko)	2012-06-21	2020-06-08	메인 파마 인터내셔널 프로프라이어터리 리미티드	이트라코나졸 조성물 및 투여형, 그리고 이것들의 사용 방법
CN104688536B (zh) *	2015-02-03	2016-06-08	常州制药厂有限公司	一种伊曲康唑制剂的制备方法

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KR100336090B1 (ko) *	1998-06-27	2002-05-27	윤승원	오일, 지방산 또는 이들의 혼합물을 함유한 난용성 약물의 고형분산제제
US6383471B1 (en) *	1999-04-06	2002-05-07	Lipocine, Inc.	Compositions and methods for improved delivery of ionizable hydrophobic therapeutic agents
KR100435141B1 (ko) *	2000-12-28	2004-06-09	한미약품 주식회사	난용성 항진균제의 경구투여용 조성물 및 그의 제조 방법
KR100455216B1 (ko) *	2001-06-27	2004-11-09	한미약품 주식회사	난용성 항진균제의 경구투여용 조성물 및 이의 제조 방법

2003
- 2003-09-09 KR KR10-2003-0063147A patent/KR100529766B1/ko not_active Expired - Fee Related
2004
- 2004-09-07 RU RU2006111477/15A patent/RU2006111477A/ru not_active Application Discontinuation
- 2004-09-07 CN CNB2004800258516A patent/CN100475211C/zh not_active Expired - Fee Related
- 2004-09-07 AU AU2004270069A patent/AU2004270069B2/en not_active Ceased
- 2004-09-07 EP EP04774524A patent/EP1663231A4/fr not_active Withdrawn
- 2004-09-07 MX MXPA06002239A patent/MXPA06002239A/es not_active Application Discontinuation
- 2004-09-07 CA CA002538019A patent/CA2538019C/fr not_active Expired - Fee Related
- 2004-09-07 BR BRPI0414192-0A patent/BRPI0414192A/pt not_active IP Right Cessation
- 2004-09-07 JP JP2006526025A patent/JP2007505103A/ja active Pending
2006
- 2006-02-15 IL IL173743A patent/IL173743A/en not_active IP Right Cessation

Also Published As

Publication number	Publication date
KR20050026169A (ko)	2005-03-15
AU2004270069A1 (en)	2005-03-17
IL173743A0 (en)	2006-07-05
AU2004270069B2 (en)	2008-03-13
EP1663231A4 (fr)	2009-04-29
JP2007505103A (ja)	2007-03-08
BRPI0414192A (pt)	2006-10-31
MXPA06002239A (es)	2006-06-20
EP1663231A1 (fr)	2006-06-07
CN1849123A (zh)	2006-10-18
CA2538019C (fr)	2009-09-01
CN100475211C (zh)	2009-04-08
RU2006111477A (ru)	2006-08-27
KR100529766B1 (ko)	2005-11-17
CA2538019A1 (fr)	2005-03-17

Legal Events

Date	Code	Title	Description
2012-12-31	FF	Patent granted
2013-12-31	MM9K	Patent not in force due to non-payment of renewal fees

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