JP5654723B2 - カンプトテシン医薬処方物およびその製法 - Google Patents
カンプトテシン医薬処方物およびその製法 Download PDFInfo
- Publication number
- JP5654723B2 JP5654723B2 JP2006545626A JP2006545626A JP5654723B2 JP 5654723 B2 JP5654723 B2 JP 5654723B2 JP 2006545626 A JP2006545626 A JP 2006545626A JP 2006545626 A JP2006545626 A JP 2006545626A JP 5654723 B2 JP5654723 B2 JP 5654723B2
- Authority
- JP
- Japan
- Prior art keywords
- container
- compounding
- contents
- desired amount
- camptothecin derivative
- 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.)
- Expired - Fee Related
Links
- 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 description 94
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 37
- KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 title claims description 33
- 229940127093 camptothecin Drugs 0.000 title claims description 33
- 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 description 33
- 238000004519 manufacturing process Methods 0.000 title description 7
- 239000000203 mixture Substances 0.000 claims description 65
- 238000013329 compounding Methods 0.000 claims description 61
- 238000009472 formulation Methods 0.000 claims description 54
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 53
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 42
- 238000002156 mixing Methods 0.000 claims description 35
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 31
- 238000010438 heat treatment Methods 0.000 claims description 27
- 239000002904 solvent Substances 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 25
- 229920001223 polyethylene glycol Polymers 0.000 claims description 19
- 239000002202 Polyethylene glycol Substances 0.000 claims description 16
- 239000002736 nonionic surfactant Substances 0.000 claims description 16
- -1 2-trimethylsilylethyl Chemical group 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- 238000005303 weighing Methods 0.000 claims description 13
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 12
- 238000001914 filtration Methods 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- 229920002556 Polyethylene Glycol 300 Polymers 0.000 claims description 10
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 claims description 9
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims description 9
- 229920000053 polysorbate 80 Polymers 0.000 claims description 9
- 229940068968 polysorbate 80 Drugs 0.000 claims description 9
- 239000003085 diluting agent Substances 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 4
- 239000006184 cosolvent Substances 0.000 claims description 4
- 238000007789 sealing Methods 0.000 claims description 4
- 229920000604 Polyethylene Glycol 200 Polymers 0.000 claims description 3
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 claims description 3
- JLFNLZLINWHATN-UHFFFAOYSA-N pentaethylene glycol Chemical compound OCCOCCOCCOCCOCCO JLFNLZLINWHATN-UHFFFAOYSA-N 0.000 claims description 3
- 229920000136 polysorbate Polymers 0.000 claims description 3
- 229950008882 polysorbate Drugs 0.000 claims description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 2
- 239000011780 sodium chloride Substances 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- FJHBVJOVLFPMQE-QFIPXVFZSA-N 7-Ethyl-10-Hydroxy-Camptothecin Chemical compound C1=C(O)C=C2C(CC)=C(CN3C(C4=C([C@@](C(=O)OC4)(O)CC)C=C33)=O)C3=NC2=C1 FJHBVJOVLFPMQE-QFIPXVFZSA-N 0.000 description 21
- 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 20
- 229960004768 irinotecan Drugs 0.000 description 20
- 235000019441 ethanol Nutrition 0.000 description 19
- 229940079593 drug Drugs 0.000 description 15
- 239000003814 drug Substances 0.000 description 15
- 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 14
- POADTFBBIXOWFJ-VWLOTQADSA-N cositecan Chemical compound C1=CC=C2C(CC[Si](C)(C)C)=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 POADTFBBIXOWFJ-VWLOTQADSA-N 0.000 description 14
- 206010028980 Neoplasm Diseases 0.000 description 12
- 238000011049 filling Methods 0.000 description 12
- 230000000259 anti-tumor effect Effects 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 201000011510 cancer Diseases 0.000 description 8
- 238000011160 research Methods 0.000 description 8
- 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 8
- 230000001954 sterilising effect Effects 0.000 description 8
- 238000004659 sterilization and disinfection Methods 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 229950009213 rubitecan Drugs 0.000 description 7
- 241000894007 species Species 0.000 description 7
- 241000282412 Homo Species 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 229960004106 citric acid Drugs 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 5
- 238000001727 in vivo Methods 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 229940002612 prodrug Drugs 0.000 description 5
- 239000000651 prodrug Substances 0.000 description 5
- 231100000419 toxicity Toxicity 0.000 description 5
- 230000001988 toxicity Effects 0.000 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 description 4
- 239000002246 antineoplastic agent Substances 0.000 description 4
- 230000023611 glucuronidation Effects 0.000 description 4
- 229930182480 glucuronide Natural products 0.000 description 4
- 150000008134 glucuronides Chemical class 0.000 description 4
- 238000011045 prefiltration Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 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 4
- 238000012546 transfer Methods 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 102000003915 DNA Topoisomerases Human genes 0.000 description 3
- 108090000323 DNA Topoisomerases Proteins 0.000 description 3
- 206010012735 Diarrhoea Diseases 0.000 description 3
- SSJQVDUAKDRWTA-CAYKMONMSA-N SN38 glucuronide Chemical compound C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1O[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O SSJQVDUAKDRWTA-CAYKMONMSA-N 0.000 description 3
- 229920006362 Teflon® Polymers 0.000 description 3
- 150000007942 carboxylates Chemical class 0.000 description 3
- LFQCJSBXBZRMTN-OAQYLSRUSA-N diflomotecan Chemical compound CC[C@@]1(O)CC(=O)OCC(C2=O)=C1C=C1N2CC2=CC3=CC(F)=C(F)C=C3N=C21 LFQCJSBXBZRMTN-OAQYLSRUSA-N 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- ZVYVPGLRVWUPMP-FYSMJZIKSA-N exatecan Chemical compound C1C[C@H](N)C2=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC3=CC(F)=C(C)C1=C32 ZVYVPGLRVWUPMP-FYSMJZIKSA-N 0.000 description 3
- 229950009429 exatecan Drugs 0.000 description 3
- 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 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 230000002503 metabolic effect Effects 0.000 description 3
- 229960000303 topotecan Drugs 0.000 description 3
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- 102000013392 Carboxylesterase Human genes 0.000 description 2
- 108010051152 Carboxylesterase Proteins 0.000 description 2
- 208000030453 Drug-Related Side Effects and Adverse reaction Diseases 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 229920002582 Polyethylene Glycol 600 Polymers 0.000 description 2
- 229920002593 Polyethylene Glycol 800 Polymers 0.000 description 2
- 206010070863 Toxicity to various agents Diseases 0.000 description 2
- 229960004543 anhydrous citric acid Drugs 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000005429 filling process Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000007689 inspection Methods 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 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 2
- 230000010534 mechanism of action Effects 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 239000002207 metabolite Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229920000847 nonoxynol Polymers 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 238000009520 phase I clinical trial Methods 0.000 description 2
- 238000009521 phase II clinical trial Methods 0.000 description 2
- 238000011146 sterile filtration Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- FBDOJYYTMIHHDH-OZBJMMHXSA-N (19S)-19-ethyl-19-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-2,4,6,8,10,14,20-heptaen-18-one Chemical compound CC[C@@]1(O)C(=O)OCC2=CN3Cc4cc5ccccc5nc4C3C=C12 FBDOJYYTMIHHDH-OZBJMMHXSA-N 0.000 description 1
- PAEZRCINULFAGO-OAQYLSRUSA-N (R)-homocamptothecin Chemical compound CC[C@@]1(O)CC(=O)OCC(C2=O)=C1C=C1N2CC2=CC3=CC=CC=C3N=C21 PAEZRCINULFAGO-OAQYLSRUSA-N 0.000 description 1
- DZNNFZGDBUXWMV-ZUWDIFAMSA-N 581079-18-7 Chemical compound C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(OC(=O)[C@H](C)NC(=O)COCCOCC(=O)N[C@@H](C)C(=O)O[C@@]3(CC)C5=C(C(N6CC7=CC8=CC=CC=C8N=C7C6=C5)=O)COC3=O)CC)C4=NC2=C1 DZNNFZGDBUXWMV-ZUWDIFAMSA-N 0.000 description 1
- 0 CCC(CC=C(c1nc(cccc2)c2cc1C1)N1C1=[U])(C(O)OCC1=*)OC(CNC(CCCCCNC(CNC(C(C)=C)=O)=O)=O)=O Chemical compound CCC(CC=C(c1nc(cccc2)c2cc1C1)N1C1=[U])(C(O)OCC1=*)OC(CNC(CCCCCNC(CNC(C(C)=C)=O)=O)=O)=O 0.000 description 1
- 241000759909 Camptotheca Species 0.000 description 1
- 230000004543 DNA replication Effects 0.000 description 1
- 230000006820 DNA synthesis Effects 0.000 description 1
- 206010059866 Drug resistance Diseases 0.000 description 1
- 241000699660 Mus musculus Species 0.000 description 1
- 229930012538 Paclitaxel Natural products 0.000 description 1
- 241001149649 Taxus wallichiana var. chinensis Species 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- SLOJCSGNHWIKIG-JNYZSSQASA-N afeletecan Chemical compound C([C@@H](C(=O)N[C@H](C(=O)O[C@@]1(CC)C2=C(C(N3CC4=CC5=CC=CC=C5N=C4C3=C2)=O)COC1=O)C(C)C)NC(=S)NC=1C=CC(O[C@@H]2[C@H]([C@H](OC)[C@H](O)[C@H](C)O2)O)=CC=1)C1=CNC=N1 SLOJCSGNHWIKIG-JNYZSSQASA-N 0.000 description 1
- 229950011393 afeletecan Drugs 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 238000002144 chemical decomposition reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000036267 drug metabolism Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 229950009073 gimatecan Drugs 0.000 description 1
- 125000003827 glycol group Chemical group 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 201000002364 leukopenia Diseases 0.000 description 1
- 231100001022 leukopenia Toxicity 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229950002654 lurtotecan Drugs 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 238000011580 nude mouse model Methods 0.000 description 1
- 230000000771 oncological effect Effects 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229960001592 paclitaxel Drugs 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 231100000004 severe toxicity Toxicity 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 231100000057 systemic toxicity Toxicity 0.000 description 1
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
Classifications
-
- 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
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
-
- 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
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/12—Carboxylic acids; Salts or anhydrides thereof
-
- 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
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
- A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
-
- 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
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
-
- 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
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
-
- 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
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- 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
- A61K9/08—Solutions
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Dermatology (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Medical Preparation Storing Or Oral Administration Devices (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US53015403P | 2003-12-17 | 2003-12-17 | |
| US60/530,154 | 2003-12-17 | ||
| PCT/US2004/036191 WO2005060871A1 (en) | 2003-12-17 | 2004-11-01 | Pharmaceutical formulations of camptothecins and process for making same |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012176425A Division JP2012214509A (ja) | 2003-12-17 | 2012-08-08 | カンプトテシン医薬処方物およびその製法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007514778A JP2007514778A (ja) | 2007-06-07 |
| JP2007514778A5 JP2007514778A5 (enExample) | 2008-12-18 |
| JP5654723B2 true JP5654723B2 (ja) | 2015-01-14 |
Family
ID=34710158
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006545626A Expired - Fee Related JP5654723B2 (ja) | 2003-12-17 | 2004-11-01 | カンプトテシン医薬処方物およびその製法 |
| JP2012176425A Pending JP2012214509A (ja) | 2003-12-17 | 2012-08-08 | カンプトテシン医薬処方物およびその製法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012176425A Pending JP2012214509A (ja) | 2003-12-17 | 2012-08-08 | カンプトテシン医薬処方物およびその製法 |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP1694242B1 (enExample) |
| JP (2) | JP5654723B2 (enExample) |
| CN (1) | CN1893892B (enExample) |
| AU (1) | AU2004305494B2 (enExample) |
| CA (1) | CA2548078C (enExample) |
| DK (1) | DK1694242T3 (enExample) |
| MX (1) | MXPA06006710A (enExample) |
| WO (1) | WO2005060871A1 (enExample) |
| ZA (1) | ZA200604757B (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GT200500310A (es) | 2004-11-19 | 2006-06-19 | Compuestos organicos | |
| SA06270147B1 (ar) | 2005-06-09 | 2009-12-22 | نوفارتيس ايه جي | عملية لتخليق 5-(مثيل–1h–إيميدازول–1-يل )–3-(ثلاثي فلـورو مثيل)–بنزامـين |
| CN100592871C (zh) * | 2008-03-14 | 2010-03-03 | 浙江林学院 | 一种杀虫剂组合物及其加工方法 |
| JP2015521190A (ja) * | 2012-05-24 | 2015-07-27 | インノファーマ，インコーポレイテッド | アプレピタント注射製剤 |
| CN102911197B (zh) * | 2012-10-19 | 2015-05-06 | 杭州海杭生物医药科技有限公司 | 喜树碱硅杂衍生物、含该衍生物的组合物及其用途 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW406020B (en) * | 1993-09-29 | 2000-09-21 | Bristol Myers Squibb Co | Stabilized pharmaceutical composition and its method for preparation and stabilizing solvent |
| US5726181A (en) * | 1995-06-05 | 1998-03-10 | Bionumerik Pharmaceuticals, Inc. | Formulations and compositions of poorly water soluble camptothecin derivatives |
| CA2262745C (en) * | 1996-08-19 | 2006-04-04 | Bionumerik Pharmaceuticals, Inc. | Highly lipophilic camptothecin derivatives |
| WO1998035940A1 (en) * | 1997-02-14 | 1998-08-20 | Bionumerik Pharmaceuticals, Inc. | Highly lipophilic camptothecin derivatives |
| US6057303A (en) * | 1998-10-20 | 2000-05-02 | Bionumerik Pharmaceuticals, Inc. | Highly lipophilic Camptothecin derivatives |
-
2004
- 2004-11-01 CN CN2004800377708A patent/CN1893892B/zh not_active Expired - Fee Related
- 2004-11-01 AU AU2004305494A patent/AU2004305494B2/en not_active Ceased
- 2004-11-01 MX MXPA06006710A patent/MXPA06006710A/es active IP Right Grant
- 2004-11-01 CA CA002548078A patent/CA2548078C/en not_active Expired - Fee Related
- 2004-11-01 EP EP04800502.9A patent/EP1694242B1/en not_active Expired - Lifetime
- 2004-11-01 WO PCT/US2004/036191 patent/WO2005060871A1/en not_active Ceased
- 2004-11-01 JP JP2006545626A patent/JP5654723B2/ja not_active Expired - Fee Related
- 2004-11-01 DK DK04800502.9T patent/DK1694242T3/da active
-
2006
- 2006-06-09 ZA ZA2006/04757A patent/ZA200604757B/en unknown
-
2012
- 2012-08-08 JP JP2012176425A patent/JP2012214509A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DK1694242T3 (da) | 2014-06-30 |
| JP2012214509A (ja) | 2012-11-08 |
| ZA200604757B (en) | 2008-04-30 |
| EP1694242A1 (en) | 2006-08-30 |
| CA2548078C (en) | 2009-05-12 |
| JP2007514778A (ja) | 2007-06-07 |
| CN1893892A (zh) | 2007-01-10 |
| AU2004305494A1 (en) | 2005-07-07 |
| CA2548078A1 (en) | 2005-07-07 |
| CN1893892B (zh) | 2012-03-28 |
| AU2004305494B2 (en) | 2009-09-10 |
| EP1694242A4 (en) | 2011-11-02 |
| EP1694242B1 (en) | 2014-04-16 |
| WO2005060871A1 (en) | 2005-07-07 |
| MXPA06006710A (es) | 2006-08-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP4009877B2 (ja) | 親脂性に富んだカンプトテシン誘導体治療薬 | |
| ES2254091T3 (es) | Composiciones farmaceuticas de ciclosporina con un acido graso hidroxilado saturado polietoxilado. | |
| JP4311369B2 (ja) | ４，５−エポキシモルヒナン誘導体を含有する安定な医薬品組成物 | |
| JP2008514706A (ja) | 安定非晶質ラパマイシン様化合物の薬学的投与形態 | |
| JP2020512328A (ja) | 新規組成物および方法 | |
| JPS6366810B2 (enExample) | ||
| HU217839B (hu) | Eljárások taxánszármazékokat tartalmazó új stabil gyógyszerkészítmények előállítására | |
| EA004307B1 (ru) | Высокоэффективные композиции, содержащие дигидроэрготамин | |
| TW450811B (en) | Lyophilizate of lipid complex of water insoluble camptothecins | |
| JP2012214509A (ja) | カンプトテシン医薬処方物およびその製法 | |
| JPH02115126A (ja) | エトポシド溶液 | |
| JPH10507177A (ja) | Ｇｆ１２０９１８ａを含む非経口医薬組成物 | |
| US20060094692A1 (en) | Pharmaceutical formulations of camptothecins and process for making same | |
| WO2020219499A1 (en) | Mini softgel naproxen composition | |
| JP7492977B2 (ja) | イリノテカン遊離塩基を含む経口投与用の医薬組成物 | |
| ES2322148T3 (es) | Medicamentos que contienen anticolinergicos para el tratamiento en las vias urinarias. | |
| CN111511349A (zh) | 包含伊立替康或其药剂学上可接受的盐的用于口服给药的药剂学组合物 | |
| CN116672330A (zh) | 一种盐酸达泊西汀复合物及其口溶膜 | |
| WO2011000811A2 (en) | Organic compounds | |
| WO2024230831A1 (zh) | 一种注射液制剂、配伍药液及其制备方法 | |
| EP4444272A1 (en) | A formulation for an effective oral administration of ciclopirox with no adversal gasterointestinal toxicity | |
| RU2279873C2 (ru) | Пероральная фармацевтическая композиция для мягких капсул, содержащая винорелбин, и способ лечения | |
| KR20040030709A (ko) | 티옥산테논을 포함하는 항종양성 제제 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20070817 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20081029 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20110105 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20110401 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20110408 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20110705 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20111220 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20120313 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20120410 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20120808 |
|
| A911 | Transfer to examiner for re-examination before appeal (zenchi) |
Free format text: JAPANESE INTERMEDIATE CODE: A911 Effective date: 20120822 |
|
| A912 | Re-examination (zenchi) completed and case transferred to appeal board |
Free format text: JAPANESE INTERMEDIATE CODE: A912 Effective date: 20120921 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20140210 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20140214 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20140310 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20140313 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140715 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140917 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20141121 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 5654723 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| S111 | Request for change of ownership or part of ownership |
Free format text: JAPANESE INTERMEDIATE CODE: R313113 |
|
| S531 | Written request for registration of change of domicile |
Free format text: JAPANESE INTERMEDIATE CODE: R313531 |
|
| R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
| LAPS | Cancellation because of no payment of annual fees |