AU2006278114B2 - Immediate release therapeutic systems for improved oral absorption of 7- [ (E) -tert-butyloxyiminomethyl] camptothecin - Google Patents
Immediate release therapeutic systems for improved oral absorption of 7- [ (E) -tert-butyloxyiminomethyl] camptothecin Download PDFInfo
- Publication number
- AU2006278114B2 AU2006278114B2 AU2006278114A AU2006278114A AU2006278114B2 AU 2006278114 B2 AU2006278114 B2 AU 2006278114B2 AU 2006278114 A AU2006278114 A AU 2006278114A AU 2006278114 A AU2006278114 A AU 2006278114A AU 2006278114 B2 AU2006278114 B2 AU 2006278114B2
- Authority
- AU
- Australia
- Prior art keywords
- pharmaceutical composition
- composition according
- capsule
- active principle
- amphiphilic
- 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.)
- Ceased
Links
- 229940127093 camptothecin Drugs 0.000 title claims abstract description 18
- VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical compound C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 title claims abstract description 17
- KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 title claims abstract description 11
- VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 title claims abstract description 11
- 239000012729 immediate-release (IR) formulation Substances 0.000 title claims abstract description 5
- 238000010521 absorption reaction Methods 0.000 title abstract description 7
- 230000001225 therapeutic effect Effects 0.000 title abstract description 4
- 239000000126 substance Substances 0.000 claims abstract description 25
- 239000011159 matrix material Substances 0.000 claims abstract description 20
- 238000002844 melting Methods 0.000 claims abstract description 16
- 230000008018 melting Effects 0.000 claims abstract description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 13
- 239000007788 liquid Substances 0.000 claims abstract description 12
- 239000002775 capsule Substances 0.000 claims description 62
- 239000000203 mixture Substances 0.000 claims description 34
- UIVFUQKYVFCEKJ-OPTOVBNMSA-N gimatecan Chemical compound C1=CC=C2C(\C=N\OC(C)(C)C)=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UIVFUQKYVFCEKJ-OPTOVBNMSA-N 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 23
- 229950009073 gimatecan Drugs 0.000 claims description 22
- 229920001223 polyethylene glycol Polymers 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 9
- 229920000136 polysorbate Polymers 0.000 claims description 7
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims description 6
- 238000007789 sealing Methods 0.000 claims description 6
- 235000019333 sodium laurylsulphate Nutrition 0.000 claims description 6
- 125000005456 glyceride group Chemical group 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 150000003626 triacylglycerols Chemical class 0.000 claims description 5
- 239000006185 dispersion Substances 0.000 claims description 4
- 229960003511 macrogol Drugs 0.000 claims description 4
- 229940068965 polysorbates Drugs 0.000 claims description 4
- 239000004141 Sodium laurylsulphate Substances 0.000 claims description 3
- 125000000129 anionic group Chemical group 0.000 claims description 3
- 239000004359 castor oil Substances 0.000 claims description 3
- 235000019438 castor oil Nutrition 0.000 claims description 3
- 239000003240 coconut oil Substances 0.000 claims description 3
- 235000019864 coconut oil Nutrition 0.000 claims description 3
- 150000002170 ethers Chemical class 0.000 claims description 3
- 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 claims description 3
- 239000000787 lecithin Substances 0.000 claims description 3
- 235000010445 lecithin Nutrition 0.000 claims description 3
- SHBUUTHKGIVMJT-UHFFFAOYSA-N Hydroxystearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OO SHBUUTHKGIVMJT-UHFFFAOYSA-N 0.000 claims description 2
- 229940106189 ceramide Drugs 0.000 claims description 2
- 150000001783 ceramides Chemical class 0.000 claims description 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 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 description 2
- 239000008387 emulsifying waxe Substances 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 239000000194 fatty acid Substances 0.000 claims description 2
- 229930195729 fatty acid Natural products 0.000 claims description 2
- 150000004665 fatty acids Chemical class 0.000 claims description 2
- 229940072106 hydroxystearate Drugs 0.000 claims description 2
- 150000002632 lipids Chemical class 0.000 claims description 2
- 229920001983 poloxamer Polymers 0.000 claims description 2
- 229940079862 sodium lauryl sarcosinate Drugs 0.000 claims description 2
- ADWNFGORSPBALY-UHFFFAOYSA-M sodium;2-[dodecyl(methyl)amino]acetate Chemical compound [Na+].CCCCCCCCCCCCN(C)CC([O-])=O ADWNFGORSPBALY-UHFFFAOYSA-M 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- FABAOYOFJNAVHB-KVVVOXFISA-N (z)-octadec-9-enoic acid;propane-1,2,3-triol Chemical compound OCC(O)CO.CCCCCCCC\C=C/CCCCCCCC(O)=O FABAOYOFJNAVHB-KVVVOXFISA-N 0.000 claims 1
- 108010010803 Gelatin Proteins 0.000 claims 1
- 235000019416 cholic acid Nutrition 0.000 claims 1
- 239000002812 cholic acid derivative Substances 0.000 claims 1
- 150000001842 cholic acids Chemical class 0.000 claims 1
- 229920000159 gelatin Polymers 0.000 claims 1
- 239000008273 gelatin Substances 0.000 claims 1
- 235000019322 gelatine Nutrition 0.000 claims 1
- 235000011852 gelatine desserts Nutrition 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 238000013019 agitation Methods 0.000 description 17
- 229940079593 drug Drugs 0.000 description 12
- 239000003814 drug Substances 0.000 description 12
- 239000007970 homogeneous dispersion Substances 0.000 description 12
- 239000000546 pharmaceutical excipient Substances 0.000 description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 10
- 238000009472 formulation Methods 0.000 description 10
- 239000007903 gelatin capsule Substances 0.000 description 10
- 239000003826 tablet Substances 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 8
- 239000008187 granular material Substances 0.000 description 8
- 239000012456 homogeneous solution Substances 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 238000000338 in vitro Methods 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 5
- 238000004090 dissolution Methods 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 239000004255 Butylated hydroxyanisole Substances 0.000 description 4
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 4
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 235000019282 butylated hydroxyanisole Nutrition 0.000 description 4
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 4
- 235000010980 cellulose Nutrition 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 4
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229940016286 microcrystalline cellulose Drugs 0.000 description 4
- 239000008108 microcrystalline cellulose Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 3
- FUXVKZWTXQUGMW-FQEVSTJZSA-N 9-Aminocamptothecin Chemical compound C1=CC(N)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 FUXVKZWTXQUGMW-FQEVSTJZSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- 230000003013 cytotoxicity Effects 0.000 description 3
- 231100000135 cytotoxicity Toxicity 0.000 description 3
- 210000001035 gastrointestinal tract Anatomy 0.000 description 3
- RZRNAYUHWVFMIP-HXUWFJFHSA-N glycerol monolinoleate Natural products CCCCCCCCC=CCCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-HXUWFJFHSA-N 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 description 3
- 229960000303 topotecan Drugs 0.000 description 3
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- OIQOAYVCKAHSEJ-UHFFFAOYSA-N 2-[2,3-bis(2-hydroxyethoxy)propoxy]ethanol;hexadecanoic acid;octadecanoic acid Chemical compound OCCOCC(OCCO)COCCO.CCCCCCCCCCCCCCCC(O)=O.CCCCCCCCCCCCCCCCCC(O)=O OIQOAYVCKAHSEJ-UHFFFAOYSA-N 0.000 description 2
- -1 5-tetrazolyl Chemical group 0.000 description 2
- 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 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 238000005280 amorphization Methods 0.000 description 2
- 239000012914 anti-clumping agent Substances 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 239000013060 biological fluid Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000008119 colloidal silica Substances 0.000 description 2
- 238000007922 dissolution test Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 229940074046 glyceryl laurate Drugs 0.000 description 2
- 229940075529 glyceryl stearate Drugs 0.000 description 2
- 238000009499 grossing Methods 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- UWKQSNNFCGGAFS-XIFFEERXSA-N irinotecan Chemical compound C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 UWKQSNNFCGGAFS-XIFFEERXSA-N 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
- 239000004530 micro-emulsion Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000010606 normalization Methods 0.000 description 2
- 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
- 239000008389 polyethoxylated castor oil Substances 0.000 description 2
- 229940113116 polyethylene glycol 1000 Drugs 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- ARIWANIATODDMH-UHFFFAOYSA-N rac-1-monolauroylglycerol Chemical compound CCCCCCCCCCCC(=O)OCC(O)CO ARIWANIATODDMH-UHFFFAOYSA-N 0.000 description 2
- 238000001226 reprecipitation Methods 0.000 description 2
- VHXNKPBCCMUMSW-FQEVSTJZSA-N rubitecan Chemical compound C1=CC([N+]([O-])=O)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VHXNKPBCCMUMSW-FQEVSTJZSA-N 0.000 description 2
- 239000007790 solid phase Substances 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 230000000707 stereoselective effect Effects 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 150000008163 sugars Chemical class 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 231100001274 therapeutic index Toxicity 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 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 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 1
- 229940114069 12-hydroxystearate Drugs 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 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 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 101100248253 Arabidopsis thaliana RH40 gene Proteins 0.000 description 1
- 206010065553 Bone marrow failure Diseases 0.000 description 1
- 241000759905 Camptotheca acuminata Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- 206010011793 Cystitis haemorrhagic Diseases 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
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 206010059024 Gastrointestinal toxicity Diseases 0.000 description 1
- JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 description 1
- 101000656751 Haloarcula marismortui (strain ATCC 43049 / DSM 3752 / JCM 8966 / VKM B-1809) 30S ribosomal protein S24e Proteins 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- 241000209018 Nyssaceae Species 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 206010041067 Small cell lung cancer Diseases 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 101710183280 Topoisomerase Proteins 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 1
- 229940043253 butylated hydroxyanisole Drugs 0.000 description 1
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 1
- 229940088954 camptosar Drugs 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229940097362 cyclodextrins Drugs 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 231100000414 gastrointestinal toxicity Toxicity 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229960004768 irinotecan Drugs 0.000 description 1
- 229960001375 lactose Drugs 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229960001021 lactose monohydrate Drugs 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 201000002364 leukopenia Diseases 0.000 description 1
- 231100001022 leukopenia Toxicity 0.000 description 1
- RVFGKBWWUQOIOU-NDEPHWFRSA-N lurtotecan Chemical compound O=C([C@]1(O)CC)OCC(C(N2CC3=4)=O)=C1C=C2C3=NC1=CC=2OCCOC=2C=C1C=4CN1CCN(C)CC1 RVFGKBWWUQOIOU-NDEPHWFRSA-N 0.000 description 1
- FYYHWMGAXLPEAU-OUBTZVSYSA-N magnesium-25 atom Chemical compound [25Mg] FYYHWMGAXLPEAU-OUBTZVSYSA-N 0.000 description 1
- 239000004531 microgranule Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000002018 overexpression Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 1
- 150000008105 phosphatidylcholines Chemical class 0.000 description 1
- 150000008104 phosphatidylethanolamines Chemical class 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920002523 polyethylene Glycol 1000 Polymers 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229940068968 polysorbate 80 Drugs 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229950009213 rubitecan Drugs 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- SLBXZQMMERXQAL-UHFFFAOYSA-M sodium;1-dodecoxy-4-hydroxy-1,4-dioxobutane-2-sulfonate Chemical compound [Na+].CCCCCCCCCCCCOC(=O)C(S(O)(=O)=O)CC([O-])=O SLBXZQMMERXQAL-UHFFFAOYSA-M 0.000 description 1
- 239000008347 soybean phospholipid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 206010043554 thrombocytopenia Diseases 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 238000005550 wet granulation Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4745—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
-
- 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
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
- A61K9/2018—Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
-
- 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
- A61K9/2031—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, polyethylene oxide, poloxamers
-
- 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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
-
- 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
- A61K9/4866—Organic macromolecular compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- 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
-
- 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
- A61K9/2081—Tablets comprising drug-containing microparticles in a substantial amount of supporting matrix; Multiparticulate tablets with microcapsules or coated microparticles according to A61K9/50
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Inorganic Chemistry (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITRM2005A000418 | 2005-08-04 | ||
| IT000418A ITRM20050418A1 (it) | 2005-08-04 | 2005-08-04 | Sistemi terapeutici a rilascio immediato per il migliorato assorbimento orale di 7-[(e)-t-butilossimminometil] camptotecina. |
| PCT/EP2006/064111 WO2007017331A2 (en) | 2005-08-04 | 2006-07-11 | Immediate release therapeutic systems for improved oral absorption of 7- [ (e) -tert-butyloxyiminomethyl] camptothecin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2006278114A1 AU2006278114A1 (en) | 2007-02-15 |
| AU2006278114B2 true AU2006278114B2 (en) | 2011-06-23 |
Family
ID=37727667
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2006278114A Ceased AU2006278114B2 (en) | 2005-08-04 | 2006-07-11 | Immediate release therapeutic systems for improved oral absorption of 7- [ (E) -tert-butyloxyiminomethyl] camptothecin |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US20090053307A1 (enExample) |
| EP (1) | EP1915153B1 (enExample) |
| JP (1) | JP5225084B2 (enExample) |
| KR (1) | KR101301548B1 (enExample) |
| CN (1) | CN101287466B (enExample) |
| AU (1) | AU2006278114B2 (enExample) |
| BR (1) | BRPI0614471A2 (enExample) |
| CA (1) | CA2612080C (enExample) |
| CY (1) | CY1114311T1 (enExample) |
| DK (1) | DK1915153T3 (enExample) |
| ES (1) | ES2407408T3 (enExample) |
| HR (1) | HRP20130364T1 (enExample) |
| IT (1) | ITRM20050418A1 (enExample) |
| MX (1) | MX2008001029A (enExample) |
| PL (1) | PL1915153T3 (enExample) |
| PT (1) | PT1915153E (enExample) |
| RS (1) | RS52777B (enExample) |
| SI (1) | SI1915153T1 (enExample) |
| WO (1) | WO2007017331A2 (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2519193C2 (ru) | 2008-09-12 | 2014-06-10 | Критикал Фармасьютикалс Лимитед | Усовершенствование всасывания терапевтических средств через слизистые оболочки или кожу |
| USD618617S1 (en) | 2008-12-30 | 2010-06-29 | Multiway Industries (Hk) Ltd. | Three way electrical plug |
| US7892036B2 (en) * | 2008-12-30 | 2011-02-22 | Multiway Industries (Hk) Ltd. | Electrical wall tap assembly |
| USD618175S1 (en) | 2009-10-15 | 2010-06-22 | Multiway Industries (Hk) Ltd. | Three-outlet surge-protected adaptor |
| USD616823S1 (en) | 2009-10-15 | 2010-06-01 | Multiway Industries (Hk) Ltd. | Single-outlet surge-protected adaptor |
| EP2510924B1 (en) * | 2009-12-08 | 2014-10-08 | IL Hwa Co., Ltd | SOLID DISPERSIONS CONTAINING 20-O-ß-D-GLUCOPYRANOSYL-20(S)-PROTOPANAXADIOL |
| USD651977S1 (en) | 2011-01-10 | 2012-01-10 | Multiway Industries (Hk) Ltd. | Multiple outlet electrical connector |
| CN108066311B (zh) * | 2017-12-26 | 2020-09-08 | 兆科（广州）肿瘤药物有限公司 | 一种吉马替康胶囊及其制备方法 |
| USD958079S1 (en) | 2019-08-30 | 2022-07-19 | Multiway Industries (Hk) Ltd. | 3-way electrical tap |
| USD955993S1 (en) | 2019-08-30 | 2022-06-28 | Multiway Industries (Hk) Ltd. | 3-way electrical tap |
| CN111529497A (zh) * | 2020-02-11 | 2020-08-14 | 兆科（广州）肿瘤药物有限公司 | 一种吉马替康药物固体分散组合物及其制备方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999006031A1 (en) * | 1997-08-01 | 1999-02-11 | Smithkline Beecham Corporation | Pharmaceutical formulation for camptothecin analogues in gelatin capsule |
| WO2000053607A1 (en) * | 1999-03-09 | 2000-09-14 | Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. | Camptothecin derivatives having antitumor activity |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5726181A (en) * | 1995-06-05 | 1998-03-10 | Bionumerik Pharmaceuticals, Inc. | Formulations and compositions of poorly water soluble camptothecin derivatives |
| NZ502569A (en) * | 1997-07-29 | 2002-05-31 | Upjohn Co | Self-emulsifying formulation for lipophilic compounds comprising a mixture of diglyceride and monoglyceride in a ratio of 9:1 to 6:4 |
| US7030155B2 (en) * | 1998-06-05 | 2006-04-18 | Sonus Pharmaceuticals, Inc. | Emulsion vehicle for poorly soluble drugs |
| AU5273200A (en) * | 1999-05-24 | 2000-12-12 | Sonus Pharmaceuticals, Inc. | Emulsion vehicle for poorly soluble drugs |
| CN101480395A (zh) * | 2004-03-26 | 2009-07-15 | 诺瓦提斯公司 | 喜树碱衍生物以固定给药方案治疗增生性疾病的用途 |
| GT200500310A (es) * | 2004-11-19 | 2006-06-19 | Compuestos organicos | |
| PL1828196T3 (pl) * | 2004-12-21 | 2013-02-28 | Sigma Tau Ind Farmaceuti | Stereoselektywny sposób wytwarzania i krystaliczne formy kamptotecyny |
-
2005
- 2005-08-04 IT IT000418A patent/ITRM20050418A1/it unknown
-
2006
- 2006-07-11 JP JP2008524462A patent/JP5225084B2/ja not_active Expired - Fee Related
- 2006-07-11 SI SI200631573T patent/SI1915153T1/sl unknown
- 2006-07-11 RS RS20130196A patent/RS52777B/sr unknown
- 2006-07-11 PT PT67777102T patent/PT1915153E/pt unknown
- 2006-07-11 BR BRPI0614471-3A patent/BRPI0614471A2/pt not_active Application Discontinuation
- 2006-07-11 CN CN200680027844.9A patent/CN101287466B/zh active Active
- 2006-07-11 WO PCT/EP2006/064111 patent/WO2007017331A2/en not_active Ceased
- 2006-07-11 MX MX2008001029A patent/MX2008001029A/es active IP Right Grant
- 2006-07-11 DK DK06777710.2T patent/DK1915153T3/da active
- 2006-07-11 CA CA2612080A patent/CA2612080C/en not_active Expired - Fee Related
- 2006-07-11 US US11/993,328 patent/US20090053307A1/en not_active Abandoned
- 2006-07-11 EP EP06777710.2A patent/EP1915153B1/en active Active
- 2006-07-11 AU AU2006278114A patent/AU2006278114B2/en not_active Ceased
- 2006-07-11 HR HRP20130364TT patent/HRP20130364T1/hr unknown
- 2006-07-11 PL PL06777710T patent/PL1915153T3/pl unknown
- 2006-07-11 ES ES06777710T patent/ES2407408T3/es active Active
- 2006-07-11 KR KR1020087003092A patent/KR101301548B1/ko not_active Expired - Fee Related
-
2013
- 2013-04-25 CY CY20131100341T patent/CY1114311T1/el unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999006031A1 (en) * | 1997-08-01 | 1999-02-11 | Smithkline Beecham Corporation | Pharmaceutical formulation for camptothecin analogues in gelatin capsule |
| WO2000053607A1 (en) * | 1999-03-09 | 2000-09-14 | Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. | Camptothecin derivatives having antitumor activity |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2007017331A3 (en) | 2007-09-27 |
| BRPI0614471A2 (pt) | 2011-03-29 |
| MX2008001029A (es) | 2008-03-14 |
| ES2407408T3 (es) | 2013-06-12 |
| HRP20130364T1 (hr) | 2013-05-31 |
| CA2612080A1 (en) | 2007-02-15 |
| US20090053307A1 (en) | 2009-02-26 |
| PL1915153T3 (pl) | 2013-09-30 |
| CN101287466A (zh) | 2008-10-15 |
| EP1915153A2 (en) | 2008-04-30 |
| KR20080031945A (ko) | 2008-04-11 |
| PT1915153E (pt) | 2013-06-05 |
| ITRM20050418A1 (it) | 2007-02-05 |
| JP5225084B2 (ja) | 2013-07-03 |
| WO2007017331A2 (en) | 2007-02-15 |
| KR101301548B1 (ko) | 2013-09-06 |
| CA2612080C (en) | 2013-09-03 |
| HK1125293A1 (en) | 2009-08-07 |
| CN101287466B (zh) | 2014-11-05 |
| DK1915153T3 (da) | 2013-06-24 |
| JP2009503013A (ja) | 2009-01-29 |
| AU2006278114A1 (en) | 2007-02-15 |
| CY1114311T1 (el) | 2016-08-31 |
| EP1915153B1 (en) | 2013-04-10 |
| SI1915153T1 (sl) | 2013-06-28 |
| RS52777B (sr) | 2013-10-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5266331A (en) | Controlled release oxycodone compositions | |
| KR100358676B1 (ko) | 급속-용해갈란타민하이드로브로마이드정제 | |
| AU2006278114B2 (en) | Immediate release therapeutic systems for improved oral absorption of 7- [ (E) -tert-butyloxyiminomethyl] camptothecin | |
| US20130203778A1 (en) | Pharmaceutical composition comprising a pyrimidineone derivative | |
| US11779586B2 (en) | Compounds comprising tricyclic heterocyclic compounds | |
| JP6355645B2 (ja) | 活性成分としてテトラゾール誘導体を含む、溶解性が改善された固体分散体 | |
| CN110946836A (zh) | 用于治疗癌症的伊立替康的固体口服剂型 | |
| KR100522239B1 (ko) | 아세트아미노펜을 함유하는 제어방출성의 경구용 제제 | |
| US6569452B1 (en) | Pharmaceutical formulations in hydroxypropylmethylcellulose capsules | |
| WO2015189778A1 (en) | Agomelatine in solution adsorbates and compositions | |
| JP4891912B2 (ja) | 非水性極性溶媒中の１０−ヒドロキシカンプトテシン化合物の溶解度を増加させるための薬剤製剤 | |
| HK1125293B (en) | Immediate release therapeutic systems for improved oral absorption of 7-[(e)-tertbutyloxyiminoxmethyl] camptothecin | |
| JP7688953B2 (ja) | Ｓｎ－３８溶解性及び経口吸収性を向上させた製剤 | |
| KR20200074759A (ko) | 두타스테라이드를 함유하는 고형제제 | |
| KR20250052834A (ko) | 프란루카스트의 생체이용률이 개선된 약제학적 조성물 및 그 제조방법 | |
| JP2003510269A (ja) | バソプレシン拮抗薬製剤および方法 | |
| JP2013503876A (ja) | インジブリンに関する薬学的組成物 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |