SK182599A3 - Soluble prodrugs of paclitaxel - Google Patents
Soluble prodrugs of paclitaxel Download PDFInfo
- Publication number
- SK182599A3 SK182599A3 SK1825-99A SK182599A SK182599A3 SK 182599 A3 SK182599 A3 SK 182599A3 SK 182599 A SK182599 A SK 182599A SK 182599 A3 SK182599 A3 SK 182599A3
- Authority
- SK
- Slovakia
- Prior art keywords
- paclitaxel
- onium salt
- patient
- dosage form
- salt
- Prior art date
Links
- 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 title claims abstract description 62
- 229930012538 Paclitaxel Natural products 0.000 title claims abstract description 60
- 229960001592 paclitaxel Drugs 0.000 title claims abstract description 60
- 239000000651 prodrug Substances 0.000 title abstract description 12
- 229940002612 prodrug Drugs 0.000 title abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 45
- 238000000034 method Methods 0.000 claims abstract description 34
- 201000010099 disease Diseases 0.000 claims abstract description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 7
- 206010028980 Neoplasm Diseases 0.000 claims description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
- 239000000047 product Substances 0.000 claims description 17
- 239000000243 solution Substances 0.000 claims description 17
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 239000002552 dosage form Substances 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 238000001990 intravenous administration Methods 0.000 claims description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 7
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 239000003623 enhancer Substances 0.000 claims description 6
- 201000011510 cancer Diseases 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 238000000605 extraction Methods 0.000 claims description 5
- 239000000843 powder Substances 0.000 claims description 5
- TYFOVYYNQGNDKH-HHPJSCBPSA-N (3s,6s,9s,12r,15s,18s,21s,24s,30s,33s)-30-ethyl-33-[(1r,2r)-1-hydroxy-2-methylhexyl]-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18,24-tetrakis(2-methylpropyl)-3,21-di(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacontane-2,5,8,11,14,17,20,23, Chemical compound CCCC[C@@H](C)[C@@H](O)[C@@H]1N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C(=O)[C@H](CC)NC1=O TYFOVYYNQGNDKH-HHPJSCBPSA-N 0.000 claims description 4
- HQWDKLAIDBOLFE-UHFFFAOYSA-M 2-fluoro-1-methylpyridin-1-ium;4-methylbenzenesulfonate Chemical group C[N+]1=CC=CC=C1F.CC1=CC=C(S([O-])(=O)=O)C=C1 HQWDKLAIDBOLFE-UHFFFAOYSA-M 0.000 claims description 4
- 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 4
- 229910019142 PO4 Inorganic materials 0.000 claims description 4
- KUSICUWKCBCAHV-ZSINMPTNSA-N [(e,1r,2r)-1-[(2s,5s,11s,14s,17s,20s,23r,26s,29s,32s)-5-ethyl-1,7,10,16,20,23,25,28,31-nonamethyl-11,17,26,29-tetrakis(2-methylpropyl)-3,6,9,12,15,18,21,24,27,30,33-undecaoxo-14,32-di(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacont-2-y Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](OC(C)=O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O KUSICUWKCBCAHV-ZSINMPTNSA-N 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 229960001265 ciclosporin Drugs 0.000 claims description 4
- 108010040764 dihydrocyclosporin A Proteins 0.000 claims description 4
- 108010040786 dihydrocyclosporin C Proteins 0.000 claims description 4
- 239000012454 non-polar solvent Substances 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 4
- 239000010452 phosphate Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 3
- 208000007766 Kaposi sarcoma Diseases 0.000 claims description 3
- 239000006193 liquid solution Substances 0.000 claims description 3
- 210000004072 lung Anatomy 0.000 claims description 3
- 201000004792 malaria Diseases 0.000 claims description 3
- 208000030761 polycystic kidney disease Diseases 0.000 claims description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 3
- JTOKYIBTLUQVQV-QRVTZXGZSA-N (3s,6s,9s,12r,15s,18s,21s,24s,30s,33s)-30-[(1r)-1-hydroxyethyl]-33-[(e,1r,2r)-1-hydroxy-2-methylhex-4-enyl]-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18,24-tetrakis(2-methylpropyl)-3,21-di(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacontan Chemical compound C\C=C\C[C@@H](C)[C@@H](O)[C@@H]1N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C(=O)[C@H]([C@@H](C)O)NC1=O JTOKYIBTLUQVQV-QRVTZXGZSA-N 0.000 claims description 2
- GNGBSKIQPUCELM-YBAOVNABSA-N (3s,6s,9s,12r,15s,18s,21s,24s,30s,33s)-30-ethyl-1,4,7,10,12,15,19,25,28-nonamethyl-33-[(e,2r)-2-methylhex-4-enyl]-6,9,18,24-tetrakis(2-methylpropyl)-3,21-di(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29, Chemical compound CC[C@@H]1NC(=O)[C@H](C[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O GNGBSKIQPUCELM-YBAOVNABSA-N 0.000 claims description 2
- ZNVBEWJRWHNZMK-SYOLRUPNSA-N (3s,6s,9s,12r,15s,18s,21s,24s,30s,33s)-33-[(e,1r,2r)-1-hydroxy-2-methylhex-4-enyl]-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18,24-tetrakis(2-methylpropyl)-3,21,30-tri(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacontane-2,5,8,11,14,17,20,2 Chemical compound C\C=C\C[C@@H](C)[C@@H](O)[C@@H]1N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C(=O)[C@H](C(C)C)NC1=O ZNVBEWJRWHNZMK-SYOLRUPNSA-N 0.000 claims description 2
- 229930105110 Cyclosporin A Natural products 0.000 claims description 2
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 claims description 2
- JTOKYIBTLUQVQV-UHFFFAOYSA-N Cyclosporin C Natural products CC=CCC(C)C(O)C1N(C)C(=O)C(C(C)C)N(C)C(=O)C(CC(C)C)N(C)C(=O)C(CC(C)C)N(C)C(=O)C(C)NC(=O)C(C)NC(=O)C(CC(C)C)N(C)C(=O)C(C(C)C)NC(=O)C(CC(C)C)N(C)C(=O)CN(C)C(=O)C(C(C)O)NC1=O JTOKYIBTLUQVQV-UHFFFAOYSA-N 0.000 claims description 2
- GNGBSKIQPUCELM-UHFFFAOYSA-N Cyclosporin F Natural products CCC1NC(=O)C(CC(C)CC=CC)N(C)C(=O)C(C(C)C)N(C)C(=O)C(CC(C)C)N(C)C(=O)C(CC(C)C)N(C)C(=O)C(C)NC(=O)C(C)NC(=O)C(CC(C)C)N(C)C(=O)C(C(C)C)NC(=O)C(CC(C)C)N(C)C(=O)CN(C)C1=O GNGBSKIQPUCELM-UHFFFAOYSA-N 0.000 claims description 2
- 108010036949 Cyclosporine Proteins 0.000 claims description 2
- 108010036941 Cyclosporins Proteins 0.000 claims description 2
- 239000007894 caplet Substances 0.000 claims description 2
- 239000002775 capsule Substances 0.000 claims description 2
- 229930182912 cyclosporin Natural products 0.000 claims description 2
- 108010019248 cyclosporin C Proteins 0.000 claims description 2
- 108010019594 cyclosporin D Proteins 0.000 claims description 2
- 108010019252 cyclosporin F Proteins 0.000 claims description 2
- 239000012467 final product Substances 0.000 claims description 2
- 239000007897 gelcap Substances 0.000 claims description 2
- 239000006194 liquid suspension Substances 0.000 claims description 2
- 239000007937 lozenge Substances 0.000 claims description 2
- 208000020816 lung neoplasm Diseases 0.000 claims description 2
- 230000036210 malignancy Effects 0.000 claims description 2
- 230000003204 osmotic effect Effects 0.000 claims description 2
- 210000000496 pancreas Anatomy 0.000 claims description 2
- 239000002245 particle Substances 0.000 claims description 2
- 239000006187 pill Substances 0.000 claims description 2
- 239000003495 polar organic solvent Substances 0.000 claims description 2
- 210000002307 prostate Anatomy 0.000 claims description 2
- 239000003826 tablet Substances 0.000 claims description 2
- 210000001519 tissue Anatomy 0.000 claims description 2
- 208000037816 tissue injury Diseases 0.000 claims description 2
- 206010020751 Hypersensitivity Diseases 0.000 claims 2
- 239000002798 polar solvent Substances 0.000 claims 2
- 206010017993 Gastrointestinal neoplasms Diseases 0.000 claims 1
- 206010027476 Metastases Diseases 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 230000004663 cell proliferation Effects 0.000 claims 1
- 238000001704 evaporation Methods 0.000 claims 1
- 230000009610 hypersensitivity Effects 0.000 claims 1
- 210000004185 liver Anatomy 0.000 claims 1
- 230000009401 metastasis Effects 0.000 claims 1
- 238000001556 precipitation Methods 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 201000001514 prostate carcinoma Diseases 0.000 claims 1
- 238000004007 reversed phase HPLC Methods 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 4
- 238000001727 in vivo Methods 0.000 abstract description 2
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- 238000002560 therapeutic procedure Methods 0.000 abstract 1
- 239000002243 precursor Substances 0.000 description 14
- 239000003814 drug Substances 0.000 description 13
- 229940079593 drug Drugs 0.000 description 12
- 238000001802 infusion Methods 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 4
- XLMXUUQMSMKFMH-UZRURVBFSA-N 2-hydroxyethyl (z,12r)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)OCCO XLMXUUQMSMKFMH-UZRURVBFSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229940106189 ceramide Drugs 0.000 description 3
- 150000001783 ceramides Chemical class 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 239000008389 polyethoxylated castor oil Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 description 2
- -1 ammonium acetate) Chemical compound 0.000 description 2
- 239000002246 antineoplastic agent Substances 0.000 description 2
- 210000000481 breast Anatomy 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000002512 chemotherapy Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000008121 dextrose Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000005414 inactive ingredient Substances 0.000 description 2
- 201000003866 lung sarcoma Diseases 0.000 description 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical class O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 150000003431 steroids Chemical class 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- 201000011057 Breast sarcoma Diseases 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 206010007559 Cardiac failure congestive Diseases 0.000 description 1
- 206010013975 Dyspnoeas Diseases 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 102000003886 Glycoproteins Human genes 0.000 description 1
- 108090000288 Glycoproteins Proteins 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 206010024264 Lethargy Diseases 0.000 description 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 206010027457 Metastases to liver Diseases 0.000 description 1
- ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical class O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 description 1
- 206010033128 Ovarian cancer Diseases 0.000 description 1
- 206010061535 Ovarian neoplasm Diseases 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- ZVOLCUVKHLEPEV-UHFFFAOYSA-N Quercetagetin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=C(O)C(O)=C(O)C=C2O1 ZVOLCUVKHLEPEV-UHFFFAOYSA-N 0.000 description 1
- HWTZYBCRDDUBJY-UHFFFAOYSA-N Rhynchosin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=CC(O)=C(O)C=C2O1 HWTZYBCRDDUBJY-UHFFFAOYSA-N 0.000 description 1
- 208000000453 Skin Neoplasms Diseases 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 229940123237 Taxane Drugs 0.000 description 1
- 241001116500 Taxus Species 0.000 description 1
- 241000202349 Taxus brevifolia Species 0.000 description 1
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 239000008351 acetate buffer Substances 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000001919 adrenal effect Effects 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000033115 angiogenesis Effects 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000001387 anti-histamine Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000000043 antiallergic agent Substances 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229920002988 biodegradable polymer Polymers 0.000 description 1
- 239000004621 biodegradable polymer Substances 0.000 description 1
- 201000011281 bladder sarcoma Diseases 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 229930004069 diterpene Natural products 0.000 description 1
- 150000004141 diterpene derivatives Chemical class 0.000 description 1
- 229960003668 docetaxel Drugs 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 210000003238 esophagus Anatomy 0.000 description 1
- 201000005691 esophagus sarcoma Diseases 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000012520 frozen sample Substances 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 229940045109 genistein Drugs 0.000 description 1
- TZBJGXHYKVUXJN-UHFFFAOYSA-N genistein Natural products C1=CC(O)=CC=C1C1=COC2=CC(O)=CC(O)=C2C1=O TZBJGXHYKVUXJN-UHFFFAOYSA-N 0.000 description 1
- 235000006539 genistein Nutrition 0.000 description 1
- ZCOLJUOHXJRHDI-CMWLGVBASA-N genistein 7-O-beta-D-glucoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 ZCOLJUOHXJRHDI-CMWLGVBASA-N 0.000 description 1
- 201000010536 head and neck cancer Diseases 0.000 description 1
- 208000014829 head and neck neoplasm Diseases 0.000 description 1
- 230000002440 hepatic effect Effects 0.000 description 1
- 206010073071 hepatocellular carcinoma Diseases 0.000 description 1
- 231100000844 hepatocellular carcinoma Toxicity 0.000 description 1
- 230000036543 hypotension Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000007972 injectable composition Substances 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 230000037041 intracellular level Effects 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 229930013032 isoflavonoid Natural products 0.000 description 1
- 150000003817 isoflavonoid derivatives Chemical class 0.000 description 1
- 235000012891 isoflavonoids Nutrition 0.000 description 1
- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 description 1
- 208000017169 kidney disease Diseases 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 201000005202 lung cancer Diseases 0.000 description 1
- 239000008176 lyophilized powder Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 210000001589 microsome Anatomy 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 230000009826 neoplastic cell growth Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 239000008203 oral pharmaceutical composition Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 208000011932 ovarian sarcoma Diseases 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 201000008079 ovary sarcoma Diseases 0.000 description 1
- 239000003186 pharmaceutical solution Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000009101 premedication Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 235000005875 quercetin Nutrition 0.000 description 1
- 229960001285 quercetin Drugs 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- KKVTYAVXTDIPAP-UHFFFAOYSA-M sodium;methanesulfonate Chemical compound [Na+].CS([O-])(=O)=O KKVTYAVXTDIPAP-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- DKPFODGZWDEEBT-QFIAKTPHSA-N taxane Chemical class C([C@]1(C)CCC[C@@H](C)[C@H]1C1)C[C@H]2[C@H](C)CC[C@@H]1C2(C)C DKPFODGZWDEEBT-QFIAKTPHSA-N 0.000 description 1
- 150000004579 taxol derivatives Chemical class 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 238000010257 thawing Methods 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 210000003932 urinary bladder Anatomy 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000002424 x-ray crystallography Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicinal Preparation (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/US1997/010746 WO1998058927A1 (en) | 1997-06-20 | 1997-06-20 | Soluble prodrugs of paclitaxel |
Publications (1)
Publication Number | Publication Date |
---|---|
SK182599A3 true SK182599A3 (en) | 2000-07-11 |
Family
ID=22261122
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SK1825-99A SK182599A3 (en) | 1997-06-20 | 1997-06-20 | Soluble prodrugs of paclitaxel |
Country Status (10)
Country | Link |
---|---|
EP (1) | EP1001769B1 (de) |
JP (1) | JP2002505682A (de) |
AT (1) | ATE219363T1 (de) |
AU (1) | AU3574097A (de) |
CA (1) | CA2294606A1 (de) |
DE (1) | DE69713526D1 (de) |
HU (1) | HUP0002521A3 (de) |
IL (1) | IL133585A0 (de) |
SK (1) | SK182599A3 (de) |
WO (1) | WO1998058927A1 (de) |
Families Citing this family (39)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003524624A (ja) * | 1999-04-09 | 2003-08-19 | ジェシー エル エス オウ | 治療薬の組織への送達を高める方法及び組成物 |
US6541508B2 (en) | 1999-09-13 | 2003-04-01 | Nobex Corporation | Taxane prodrugs |
US6713454B1 (en) | 1999-09-13 | 2004-03-30 | Nobex Corporation | Prodrugs of etoposide and etoposide analogs |
US6380405B1 (en) | 1999-09-13 | 2002-04-30 | Nobex Corporation | Taxane prodrugs |
US6638906B1 (en) | 1999-12-13 | 2003-10-28 | Nobex Corporation | Amphiphilic polymers and polypeptide conjugates comprising same |
EP1365759A2 (de) * | 2001-01-18 | 2003-12-03 | PHARMACIA & UPJOHN COMPANY | Paclitaxel-enthaltende chemotherapeutische mikroemulsionen mit verbesserter oraler bioverfügbarkeit |
US7115565B2 (en) | 2001-01-18 | 2006-10-03 | Pharmacia & Upjohn Company | Chemotherapeutic microemulsion compositions of paclitaxel with improved oral bioavailability |
US7351542B2 (en) | 2002-05-20 | 2008-04-01 | The Regents Of The University Of California | Methods of modulating tubulin deacetylase activity |
EP2390262A1 (de) | 2003-05-16 | 2011-11-30 | Intermune, Inc. | Synthetische Chemokinrezeptorliganden und Verwendungsverfahren dafür |
US7597884B2 (en) | 2004-08-09 | 2009-10-06 | Alios Biopharma, Inc. | Hyperglycosylated polypeptide variants and methods of use |
US8691780B2 (en) | 2005-02-17 | 2014-04-08 | The Board Of Trustees Of The Leland Stanford Junior University | Txr1 and enhanced taxane sensitivity based on the modulation of a pathway mediated thereby |
JP5523313B2 (ja) | 2007-07-03 | 2014-06-18 | チルドレンズ ホスピタル アンド リサーチ センター アット オークランド | ポリシアル酸誘導体、製造方法、ならびにがん抗原産生の増強およびターゲティングにおける使用 |
ES2530462T3 (es) | 2008-05-22 | 2015-03-03 | Galera Therapeutics Llc | Combinación terapia antitumoral |
EP2310507A4 (de) | 2008-07-08 | 2013-03-20 | David Gladstone Inst | Verfahren und zusammensetzungen zur angiogenesemodulierung |
US9359376B2 (en) * | 2011-04-08 | 2016-06-07 | Sphaera Pharma Pte. Ltd | Substituted methylformyl reagents and method of using same to modify physicochemical and/or pharmacokinetic properties of compounds |
EP3539563A1 (de) | 2012-07-19 | 2019-09-18 | Redwood Bioscience, Inc. | Für cd22 spezifischer antikörper und verfahren zur verwendung davon |
EP2916835A4 (de) | 2012-11-12 | 2016-07-27 | Redwood Bioscience Inc | Verbindungen und verfahren zur herstellung eines konjugats |
PL2956175T3 (pl) | 2013-02-15 | 2018-05-30 | The Regents Of The University Of California | Chimeryczny receptor antygenowy i sposoby jego zastosowania |
EP2970124B1 (de) | 2013-03-14 | 2019-05-22 | The Board of Trustees of the Leland Stanford Junior University | Mitochondriale aldehyd-dehydrogenase-2-modulatoren und verfahren zur verwendung davon |
WO2015081282A1 (en) | 2013-11-27 | 2015-06-04 | Redwood Bioscience, Inc. | Hydrazinyl-pyrrolo compounds and methods for producing a conjugate |
EP3107899B1 (de) | 2014-02-19 | 2020-08-12 | Aviv Therapeutics, Inc. | Mitochondrial aldehyddehydrogenase 2 (aldh2)-bindende polycyclische amide und deren verwendung zur behandlung von krebs |
WO2017083637A1 (en) | 2015-11-12 | 2017-05-18 | The Board Of Trustees Of The Leland Stanford Junior University | Cell-penetrating, guanidinium-rich oligophosphotriesters for drug and probe delivery |
US20210206826A1 (en) | 2015-11-19 | 2021-07-08 | The Regents Of The University Of California | Conditionally repressible immune cell receptors and methods of use thereof |
EP3231421A1 (de) | 2016-04-11 | 2017-10-18 | Greenaltech, S.L. | Verwendungen eines carotenoids bei der behandlung oder prävention von durch stress verursachten störungen |
CN109071634A (zh) | 2016-04-26 | 2018-12-21 | R.P.谢勒技术有限责任公司 | 抗体偶联物及其制备和使用方法 |
EP3463308B1 (de) | 2016-06-01 | 2021-12-01 | Servier IP UK Limited | Formulierungen von polyalkylen-oxid-asparaginase und verfahren zur herstellung und verwendung davon |
AU2018211081A1 (en) | 2017-01-18 | 2019-07-18 | Bioatla, Inc. | Chimeric antigen receptors against Axl or Ror2 and methods of use thereof |
EP3388082A1 (de) | 2017-04-13 | 2018-10-17 | Galera Labs, LLC | Kombinationskrebsimmuntherapie mit makrocyclischem pentaaza-ringkomplex |
CA3090129A1 (en) | 2018-01-31 | 2019-08-08 | Galera Labs, Llc | Combination cancer therapy with pentaaza macrocyclic ring complex and platinum-based anticancer agent |
US11660266B2 (en) | 2018-04-11 | 2023-05-30 | Ohio State Innovation Foundation | Methods and compositions for sustained release microparticles for ocular drug delivery |
EP3823674A4 (de) | 2018-07-18 | 2022-12-28 | Manzanita Pharmaceuticals, Inc. | Konjugate zur abgabe eines krebsmittels an nervenzellen, verwendungsverfahren und verfahren zu deren herstellung |
CN113692413A (zh) | 2019-04-02 | 2021-11-23 | 肯乔克蒂生物技术股份有限公司 | 外排泵-癌症抗原多特异性抗体以及与其相关的组合物、试剂、试剂盒和方法 |
JP2023512196A (ja) | 2020-01-29 | 2023-03-24 | ケンジョッケティ バイオテクノロジー,インク. | 抗mdr1抗体およびその使用 |
WO2021247426A1 (en) | 2020-06-04 | 2021-12-09 | Kenjockety Biotechnology, Inc. | Anti-abcg2 antibodies and uses thereof |
AU2021283080A1 (en) | 2020-06-04 | 2022-12-15 | Kenjockety Biotechnology, Inc. | ABCG2 efflux pump-cancer antigen multi-specific antibodies and compositions, reagents, kits and methods related thereto |
CN116490522A (zh) | 2020-09-02 | 2023-07-25 | 肯乔克蒂生物技术股份有限公司 | 抗abcc1抗体及其应用 |
AU2021380659A1 (en) | 2020-11-13 | 2023-06-01 | Kenjockety Biotechnology, Inc. | Anti-mrp4 (encoded by abcc4 gene) antibodies and uses thereof |
WO2023114658A1 (en) | 2021-12-13 | 2023-06-22 | Kenjockety Biotechnology, Inc. | Anti-abcb1 antibodies |
WO2023159220A1 (en) | 2022-02-18 | 2023-08-24 | Kenjockety Biotechnology, Inc. | Anti-cd47 antibodies |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1997015571A1 (en) * | 1995-10-27 | 1997-05-01 | The Scripps Research Institute | Method for treating cancer using taxoid onium salt prodrugs |
JP2002500667A (ja) * | 1997-05-27 | 2002-01-08 | ベーカー ノートン ファーマシューティカルズ インコーポレイテッド | 人間の患者に対して経口的にタキサン類を投薬するための方法及び組成物 |
-
1997
- 1997-06-20 AU AU35740/97A patent/AU3574097A/en not_active Abandoned
- 1997-06-20 HU HU0002521A patent/HUP0002521A3/hu unknown
- 1997-06-20 DE DE69713526T patent/DE69713526D1/de not_active Expired - Lifetime
- 1997-06-20 CA CA002294606A patent/CA2294606A1/en not_active Abandoned
- 1997-06-20 WO PCT/US1997/010746 patent/WO1998058927A1/en not_active Application Discontinuation
- 1997-06-20 JP JP50434699A patent/JP2002505682A/ja not_active Ceased
- 1997-06-20 SK SK1825-99A patent/SK182599A3/sk unknown
- 1997-06-20 AT AT97932226T patent/ATE219363T1/de not_active IP Right Cessation
- 1997-06-20 IL IL13358597A patent/IL133585A0/xx unknown
- 1997-06-20 EP EP97932226A patent/EP1001769B1/de not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
JP2002505682A (ja) | 2002-02-19 |
EP1001769B1 (de) | 2002-06-19 |
HUP0002521A2 (hu) | 2001-06-28 |
HUP0002521A3 (en) | 2002-04-29 |
AU3574097A (en) | 1999-01-04 |
EP1001769A1 (de) | 2000-05-24 |
WO1998058927A1 (en) | 1998-12-30 |
IL133585A0 (en) | 2001-04-30 |
CA2294606A1 (en) | 1998-12-30 |
EP1001769A4 (de) | 2000-05-24 |
ATE219363T1 (de) | 2002-07-15 |
DE69713526D1 (de) | 2002-07-25 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
SK182599A3 (en) | Soluble prodrugs of paclitaxel | |
US5817840A (en) | Water soluble taxol derivatives | |
KR101154351B1 (ko) | 암 치료를 위한 벤조퀴논-함유 안사마이신의 유사체 | |
US11147793B2 (en) | Taxane analogs for the treatment of brain cancer | |
KR20020082458A (ko) | 탁산 프로드럭 | |
SK15012000A3 (sk) | Ekteinascidínová zlúčenina, farmaceutický prostriedok, ktorý ju obsahuje, a jej použitie | |
AU2012275953B2 (en) | Acid-labile lipophilic prodrugs of cancer chemotherapeutic agents | |
CN112245591A (zh) | 化疗药物-低氧激活前药一体化前药自组装纳米粒的构建 | |
JP2004529116A (ja) | タキサンプロドラッグ | |
KR20110026311A (ko) | 엔테카비어의 신규한 염 | |
US6153756A (en) | Soluble prodrugs of paclitaxel | |
KR19990008184A (ko) | 수용성 신규 플루오로에틸캠프토테신유도체 및 그의 제조 방법 | |
US20080255080A1 (en) | Hydroquinone Ansamycin Formulations | |
MXPA99011948A (es) | Profarmacos solubles de paclitaxel | |
KR20010013975A (ko) | 파클리탁셀의 가용성 약물전구체 | |
AU1543002A (en) | Soluble prodrugs of paclitaxel | |
NZ501888A (en) | Paclitaxel 2'-methyl-pyridinium mesylate, phosphate or bicarbonate salts | |
CZ465199A3 (cs) | Rozpustné prekurzory paclitaxelu a způsoby jejich přípravy | |
US20040122081A1 (en) | Pharmaceutical compositions and methods of using taxane derivatives | |
CN105732651A (zh) | 一种小分子肺靶向药物 | |
CN112138001A (zh) | 一种槲皮素-低分子肝素-紫杉醇结合物、制备方法及应用 | |
CN1262683A (zh) | 可溶性紫杉醇前药 | |
CN110227164A (zh) | 含酮羰基的疏水性抗肿瘤药物及其缀合物、含有缀合物的纳米制剂及其制备方法及应用 | |
CN111285911B (zh) | Gem-1mt两亲小分子化合物及其制剂、制备方法和应用 | |
US20050054716A1 (en) | Pharmaceutical compositions and methods of using taxane derivatives |