CA2693057A1

CA2693057A1 - Formulations orales pour du picoplatine

Formulations orales pour du picoplatine Download PDF

Info

Publication number: CA2693057A1
Authority: CA; Canada
Prior art keywords: picoplatin; formulation; cancer; oil; combination
Prior art date: 2007-07-16
Legal status : Abandoned

Application number

CA 2693057

Other languages

English (en)

Inventor

Andrew Xian Chen

Cheni Kwok

Christopher A. Procyshyn

Current Assignee

Poniard Pharmaceuticals Inc

Original Assignee

Individual

Priority date

2007-07-16

Filing date

2008-07-16

Publication date

2009-01-22

2008-07-16 Application filed by Individual filed Critical Individual

2009-01-22 Publication of CA2693057A1 publication Critical patent/CA2693057A1/fr

Status Abandoned legal-status Critical Current

Links

229950005566 picoplatin Drugs 0.000 title claims abstract description 399
IIMIOEBMYPRQGU-UHFFFAOYSA-L picoplatin Chemical compound N.[Cl-].[Cl-].[Pt+2].CC1=CC=CC=N1 IIMIOEBMYPRQGU-UHFFFAOYSA-L 0.000 title claims abstract description 377
239000000203 mixture Substances 0.000 title claims abstract description 200
238000009472 formulation Methods 0.000 title claims abstract description 152
238000000034 method Methods 0.000 claims abstract description 92
239000003921 oil Substances 0.000 claims abstract description 61
239000000725 suspension Substances 0.000 claims abstract description 44
239000002246 antineoplastic agent Substances 0.000 claims abstract description 37
238000002360 preparation method Methods 0.000 claims abstract description 20
239000007962 solid dispersion Substances 0.000 claims abstract description 18
239000002245 particle Substances 0.000 claims description 67
235000019198 oils Nutrition 0.000 claims description 60
239000002904 solvent Substances 0.000 claims description 56
229920001223 polyethylene glycol Polymers 0.000 claims description 51
239000002105 nanoparticle Substances 0.000 claims description 44
206010028980 Neoplasm Diseases 0.000 claims description 43
239000002202 Polyethylene glycol Substances 0.000 claims description 43
239000000787 lecithin Substances 0.000 claims description 43
235000010445 lecithin Nutrition 0.000 claims description 43
239000007787 solid Substances 0.000 claims description 43
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 claims description 42
229940067606 lecithin Drugs 0.000 claims description 42
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 39
239000002609 medium Substances 0.000 claims description 33
239000011159 matrix material Substances 0.000 claims description 30
239000006185 dispersion Substances 0.000 claims description 28
201000011510 cancer Diseases 0.000 claims description 27
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102000011632 Caseins Human genes 0.000 claims description 21
108010076119 Caseins Proteins 0.000 claims description 21
239000004094 surface-active agent Substances 0.000 claims description 21
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 21
239000003995 emulsifying agent Substances 0.000 claims description 20
238000002156 mixing Methods 0.000 claims description 19
150000002194 fatty esters Chemical class 0.000 claims description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
239000007788 liquid Substances 0.000 claims description 16
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 claims description 13
206010041067 Small cell lung cancer Diseases 0.000 claims description 12
239000000155 melt Substances 0.000 claims description 12
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 claims description 12
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims description 12
229940068968 polysorbate 80 Drugs 0.000 claims description 12
229920000053 polysorbate 80 Polymers 0.000 claims description 12
208000000587 small cell lung carcinoma Diseases 0.000 claims description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
AOBORMOPSGHCAX-UHFFFAOYSA-N Tocophersolan Chemical compound OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-UHFFFAOYSA-N 0.000 claims description 11
239000012736 aqueous medium Substances 0.000 claims description 11
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BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 claims description 11
235000021240 caseins Nutrition 0.000 claims description 11
239000012943 hotmelt Substances 0.000 claims description 11
DMBUODUULYCPAK-UHFFFAOYSA-N 1,3-bis(docosanoyloxy)propan-2-yl docosanoate Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCCCCCC DMBUODUULYCPAK-UHFFFAOYSA-N 0.000 claims description 10
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229940080237 sodium caseinate Drugs 0.000 claims description 10
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 claims description 10
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229920002565 Polyethylene Glycol 400 Polymers 0.000 claims description 8
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239000002256 antimetabolite Substances 0.000 claims description 8
239000003381 stabilizer Substances 0.000 claims description 8
239000006228 supernatant Substances 0.000 claims description 8
LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 claims description 7
HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 claims description 7
229940100198 alkylating agent Drugs 0.000 claims description 7
239000002168 alkylating agent Substances 0.000 claims description 7
239000004359 castor oil Substances 0.000 claims description 7
235000019438 castor oil Nutrition 0.000 claims description 7
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 7
230000008569 process Effects 0.000 claims description 7
229960000303 topotecan Drugs 0.000 claims description 7
JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 claims description 6
102000009465 Growth Factor Receptors Human genes 0.000 claims description 6
108010009202 Growth Factor Receptors Proteins 0.000 claims description 6
239000002147 L01XE04 - Sunitinib Substances 0.000 claims description 6
206010058467 Lung neoplasm malignant Diseases 0.000 claims description 6
206010033128 Ovarian cancer Diseases 0.000 claims description 6
206010061535 Ovarian neoplasm Diseases 0.000 claims description 6
206010060862 Prostate cancer Diseases 0.000 claims description 6
208000000236 Prostatic Neoplasms Diseases 0.000 claims description 6
229940123237 Taxane Drugs 0.000 claims description 6
239000002775 capsule Substances 0.000 claims description 6
150000001720 carbohydrates Chemical class 0.000 claims description 6
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YJGVMLPVUAXIQN-XVVDYKMHSA-N podophyllotoxin Chemical class COC1=C(OC)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@H](O)[C@@H]3[C@@H]2C(OC3)=O)=C1 YJGVMLPVUAXIQN-XVVDYKMHSA-N 0.000 claims description 6
229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 claims description 6
239000003549 soybean oil Substances 0.000 claims description 6
235000012424 soybean oil Nutrition 0.000 claims description 6
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 claims description 6
206010005003 Bladder cancer Diseases 0.000 claims description 5
206010006187 Breast cancer Diseases 0.000 claims description 5
208000026310 Breast neoplasm Diseases 0.000 claims description 5
206010008342 Cervix carcinoma Diseases 0.000 claims description 5
208000000461 Esophageal Neoplasms Diseases 0.000 claims description 5
208000007766 Kaposi sarcoma Diseases 0.000 claims description 5
206010025323 Lymphomas Diseases 0.000 claims description 5
206010027406 Mesothelioma Diseases 0.000 claims description 5
206010030155 Oesophageal carcinoma Diseases 0.000 claims description 5
206010061902 Pancreatic neoplasm Diseases 0.000 claims description 5
229920002690 Polyoxyl 40 HydrogenatedCastorOil Polymers 0.000 claims description 5
206010039491 Sarcoma Diseases 0.000 claims description 5
208000024313 Testicular Neoplasms Diseases 0.000 claims description 5
206010057644 Testis cancer Diseases 0.000 claims description 5
208000000728 Thymus Neoplasms Diseases 0.000 claims description 5
208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 5
208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims description 5
208000002495 Uterine Neoplasms Diseases 0.000 claims description 5
229940122803 Vinca alkaloid Drugs 0.000 claims description 5
210000000988 bone and bone Anatomy 0.000 claims description 5
208000002458 carcinoid tumor Diseases 0.000 claims description 5
201000010881 cervical cancer Diseases 0.000 claims description 5
GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 5
AAKJLRGGTJKAMG-UHFFFAOYSA-N erlotinib Chemical compound C=12C=C(OCCOC)C(OCCOC)=CC2=NC=NC=1NC1=CC=CC(C#C)=C1 AAKJLRGGTJKAMG-UHFFFAOYSA-N 0.000 claims description 5
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238000004108 freeze drying Methods 0.000 claims description 5
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201000010536 head and neck cancer Diseases 0.000 claims description 5
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201000001441 melanoma Diseases 0.000 claims description 5
208000014761 nasopharyngeal type undifferentiated carcinoma Diseases 0.000 claims description 5
WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 5
201000002528 pancreatic cancer Diseases 0.000 claims description 5
208000008443 pancreatic carcinoma Diseases 0.000 claims description 5
239000008389 polyethoxylated castor oil Substances 0.000 claims description 5
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210000002784 stomach Anatomy 0.000 claims description 5
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235000019483 Peanut oil Nutrition 0.000 claims description 4
229960002550 amrubicin Drugs 0.000 claims description 4
VJZITPJGSQKZMX-XDPRQOKASA-N amrubicin Chemical compound O([C@H]1C[C@](CC2=C(O)C=3C(=O)C4=CC=CC=C4C(=O)C=3C(O)=C21)(N)C(=O)C)[C@H]1C[C@H](O)[C@H](O)CO1 VJZITPJGSQKZMX-XDPRQOKASA-N 0.000 claims description 4
229960000397 bevacizumab Drugs 0.000 claims description 4
230000022131 cell cycle Effects 0.000 claims description 4
YMNCVRSYJBNGLD-KURKYZTESA-N cephalotaxine Chemical class C([C@@]12C=C([C@H]([C@H]2C2=C3)O)OC)CCN1CCC2=CC1=C3OCO1 YMNCVRSYJBNGLD-KURKYZTESA-N 0.000 claims description 4
229960005395 cetuximab Drugs 0.000 claims description 4
235000012343 cottonseed oil Nutrition 0.000 claims description 4
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229960004679 doxorubicin Drugs 0.000 claims description 4
239000008157 edible vegetable oil Substances 0.000 claims description 4
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229920001993 poloxamer 188 Polymers 0.000 claims description 4
229940044519 poloxamer 188 Drugs 0.000 claims description 4
229960001796 sunitinib Drugs 0.000 claims description 4
WINHZLLDWRZWRT-ATVHPVEESA-N sunitinib Chemical compound CCN(CC)CCNC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C WINHZLLDWRZWRT-ATVHPVEESA-N 0.000 claims description 4
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 claims description 4
229960002066 vinorelbine Drugs 0.000 claims description 4
VVIAGPKUTFNRDU-UHFFFAOYSA-N 6S-folinic acid Natural products C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 VVIAGPKUTFNRDU-UHFFFAOYSA-N 0.000 claims description 3
GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims description 3
239000005551 L01XE03 - Erlotinib Substances 0.000 claims description 3
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ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound 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 claims description 3
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VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 claims description 3
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VVIAGPKUTFNRDU-ABLWVSNPSA-N folinic acid Chemical compound C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 VVIAGPKUTFNRDU-ABLWVSNPSA-N 0.000 claims description 3
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