CA2524478A1 - Lipid platinum complexes and methods of use thereof - Google Patents

Info

Publication number

CA2524478A1

CA2524478A1 CA002524478A CA2524478A CA2524478A1 CA 2524478 A1 CA2524478 A1 CA 2524478A1 CA 002524478 A CA002524478 A CA 002524478A CA 2524478 A CA2524478 A CA 2524478A CA 2524478 A1 CA2524478 A1 CA 2524478A1

Authority

CA

Canada

Prior art keywords

platinum complex

lipid

lipid platinum

complex

liposomal

Prior art date

2003-05-02

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• -1 Lipid platinum complexes Chemical class 0.000 title claims abstract description 109
• 238000000034 method Methods 0.000 title claims abstract description 76
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 352
• 150000002632 lipids Chemical class 0.000 claims abstract description 219
• 229910052697 platinum Inorganic materials 0.000 claims abstract description 171
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 109
• 201000011510 cancer Diseases 0.000 claims abstract description 86
• 150000001875 compounds Chemical class 0.000 claims abstract description 79
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 38
• 239000002552 dosage form Substances 0.000 claims abstract description 10
• 239000003446 ligand Substances 0.000 claims description 95
• 235000002639 sodium chloride Nutrition 0.000 claims description 59
• 239000002246 antineoplastic agent Substances 0.000 claims description 47
• 150000003839 salts Chemical class 0.000 claims description 45
• 239000002502 liposome Substances 0.000 claims description 42
• 150000003904 phospholipids Chemical group 0.000 claims description 42
• PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol Substances OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 34
• 239000000243 solution Substances 0.000 claims description 30
• 150000004985 diamines Chemical class 0.000 claims description 22
• GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims description 20
• AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 claims description 20
• 229960002949 fluorouracil Drugs 0.000 claims description 20
• HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 claims description 20
• 239000004094 surface-active agent Substances 0.000 claims description 18
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 16
• 241000282414 Homo sapiens Species 0.000 claims description 15
• 239000003937 drug carrier Substances 0.000 claims description 15
• 229960005277 gemcitabine Drugs 0.000 claims description 15
• SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 claims description 15
• CITHEXJVPOWHKC-UUWRZZSWSA-N 1,2-di-O-myristoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCC CITHEXJVPOWHKC-UUWRZZSWSA-N 0.000 claims description 13
• GAGWJHPBXLXJQN-UHFFFAOYSA-N Capecitabine Natural products C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1C1C(O)C(O)C(C)O1 GAGWJHPBXLXJQN-UHFFFAOYSA-N 0.000 claims description 13
• 229960004117 capecitabine Drugs 0.000 claims description 13
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
• 229960003724 dimyristoylphosphatidylcholine Drugs 0.000 claims description 13
• 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
• GAGWJHPBXLXJQN-UORFTKCHSA-N Capecitabine Chemical compound C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1[C@H]1[C@H](O)[C@H](O)[C@@H](C)O1 GAGWJHPBXLXJQN-UORFTKCHSA-N 0.000 claims description 12
• SSJXIUAHEKJCMH-LWOQYNTDSA-N (1r)-cyclohexane-1,2-diamine Chemical compound NC1CCCC[C@H]1N SSJXIUAHEKJCMH-LWOQYNTDSA-N 0.000 claims description 11
• 206010009944 Colon cancer Diseases 0.000 claims description 11
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 10
• PORPENFLTBBHSG-MGBGTMOVSA-N 1,2-dihexadecanoyl-sn-glycerol-3-phosphate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCC PORPENFLTBBHSG-MGBGTMOVSA-N 0.000 claims description 10
• 239000003981 vehicle Substances 0.000 claims description 10
• ATBOMIWRCZXYSZ-XZBBILGWSA-N [1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-hexadecanoyloxypropan-2-yl] (9e,12e)-octadeca-9,12-dienoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(COP(O)(=O)OCC(O)CO)OC(=O)CCCCCCC\C=C\C\C=C\CCCCC ATBOMIWRCZXYSZ-XZBBILGWSA-N 0.000 claims description 9
• 239000011780 sodium chloride Substances 0.000 claims description 9
• PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 8
• 125000004432 carbon atom Chemical group C* 0.000 claims description 8
• JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical group OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 claims description 7
• 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 7
• 125000002947 alkylene group Chemical group 0.000 claims description 7
• 239000002111 antiemetic agent Substances 0.000 claims description 7
• 229940125683 antiemetic agent Drugs 0.000 claims description 7
• 125000002993 cycloalkylene group Chemical group 0.000 claims description 7
• 125000001475 halogen functional group Chemical group 0.000 claims description 7
• SSJXIUAHEKJCMH-OLQVQODUSA-N (1s,2r)-cyclohexane-1,2-diamine Chemical compound N[C@H]1CCCC[C@H]1N SSJXIUAHEKJCMH-OLQVQODUSA-N 0.000 claims description 6
• 125000006686 (C1-C24) alkyl group Chemical group 0.000 claims description 6
• 108010071942 Colony-Stimulating Factors Proteins 0.000 claims description 6
• 229960005160 dimyristoylphosphatidylglycerol Drugs 0.000 claims description 6
• BPHQZTVXXXJVHI-AJQTZOPKSA-N ditetradecanoyl phosphatidylglycerol Chemical compound CCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@@H](O)CO)OC(=O)CCCCCCCCCCCCC BPHQZTVXXXJVHI-AJQTZOPKSA-N 0.000 claims description 6
• 230000003394 haemopoietic effect Effects 0.000 claims description 6
• 239000002736 nonionic surfactant Substances 0.000 claims description 6
• 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 5
• 239000007864 aqueous solution Substances 0.000 claims description 5
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 5
• 201000002528 pancreatic cancer Diseases 0.000 claims description 5
• 208000008443 pancreatic carcinoma Diseases 0.000 claims description 5
• 206010027406 Mesothelioma Diseases 0.000 claims description 4
• 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 4
• 210000004556 brain Anatomy 0.000 claims description 4
• LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 claims description 4
• 239000002953 phosphate buffered saline Substances 0.000 claims description 4
• 150000008104 phosphatidylethanolamines Chemical class 0.000 claims description 4
• SNKAWJBJQDLSFF-NVKMUCNASA-N 1,2-dioleoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCC SNKAWJBJQDLSFF-NVKMUCNASA-N 0.000 claims description 3
• NRJAVPSFFCBXDT-HUESYALOSA-N 1,2-distearoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC NRJAVPSFFCBXDT-HUESYALOSA-N 0.000 claims description 3
• BIABMEZBCHDPBV-MPQUPPDSSA-N 1,2-palmitoyl-sn-glycero-3-phospho-(1'-sn-glycerol) Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@@H](O)CO)OC(=O)CCCCCCCCCCCCCCC BIABMEZBCHDPBV-MPQUPPDSSA-N 0.000 claims description 3
• PZNPLUBHRSSFHT-RRHRGVEJSA-N 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[C@@H](COP([O-])(=O)OCC[N+](C)(C)C)COC(=O)CCCCCCCCCCCCCCC PZNPLUBHRSSFHT-RRHRGVEJSA-N 0.000 claims description 3
• NEZDNQCXEZDCBI-UHFFFAOYSA-N 2-azaniumylethyl 2,3-di(tetradecanoyloxy)propyl phosphate Chemical compound CCCCCCCCCCCCCC(=O)OCC(COP(O)(=O)OCCN)OC(=O)CCCCCCCCCCCCC NEZDNQCXEZDCBI-UHFFFAOYSA-N 0.000 claims description 3
• FVJZSBGHRPJMMA-IOLBBIBUSA-N PG(18:0/18:0) Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@@H](O)CO)OC(=O)CCCCCCCCCCCCCCCCC FVJZSBGHRPJMMA-IOLBBIBUSA-N 0.000 claims description 3
• DSNRWDQKZIEDDB-GCMPNPAFSA-N [(2r)-3-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-2-[(z)-octadec-9-enoyl]oxypropyl] (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](COP(O)(=O)OCC(O)CO)OC(=O)CCCCCCC\C=C/CCCCCCCC DSNRWDQKZIEDDB-GCMPNPAFSA-N 0.000 claims description 3
• 150000007942 carboxylates Chemical class 0.000 claims description 3
• KILNVBDSWZSGLL-KXQOOQHDSA-N 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC KILNVBDSWZSGLL-KXQOOQHDSA-N 0.000 claims description 2
• SLKDGVPOSSLUAI-PGUFJCEWSA-N 1,2-dihexadecanoyl-sn-glycero-3-phosphoethanolamine zwitterion Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OCCN)OC(=O)CCCCCCCCCCCCCCC SLKDGVPOSSLUAI-PGUFJCEWSA-N 0.000 claims description 2
• RFVFQQWKPSOBED-PSXMRANNSA-N 1-myristoyl-2-palmitoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)O[C@@H](COP([O-])(=O)OCC[N+](C)(C)C)COC(=O)CCCCCCCCCCCCC RFVFQQWKPSOBED-PSXMRANNSA-N 0.000 claims description 2
• 102000007644 Colony-Stimulating Factors Human genes 0.000 claims description 2
• JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 claims description 2
• 125000000129 anionic group Chemical group 0.000 claims description 2
• 125000002091 cationic group Chemical group 0.000 claims description 2
• SGLJYTWMWIAGEU-KNCHESJLSA-N (1s,2r)-cyclohexane-1,2-diamine;platinum(2+) Chemical compound [Pt+2].N[C@H]1CCCC[C@H]1N SGLJYTWMWIAGEU-KNCHESJLSA-N 0.000 claims 2
• 239000000203 mixture Chemical class 0.000 abstract description 81
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
• 229910001868 water Inorganic materials 0.000 description 27
• 210000004027 cell Anatomy 0.000 description 25
• 239000003112 inhibitor Substances 0.000 description 23
• 239000000725 suspension Substances 0.000 description 23
• 238000011282 treatment Methods 0.000 description 23
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
• 239000013543 active substance Substances 0.000 description 17
• DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 17
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
• 239000007924 injection Substances 0.000 description 15
• 238000002347 injection Methods 0.000 description 15
• 239000007788 liquid Substances 0.000 description 15
• 229960004316 cisplatin Drugs 0.000 description 14
• 238000009472 formulation Methods 0.000 description 13
• 239000003795 chemical substances by application Substances 0.000 description 12
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 12
• 150000003057 platinum Chemical class 0.000 description 12
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• 238000001959 radiotherapy Methods 0.000 description 11
• 238000002560 therapeutic procedure Methods 0.000 description 11
• 241001465754 Metazoa Species 0.000 description 10
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
• 239000000443 aerosol Substances 0.000 description 9
• VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 description 9
• 229940079593 drug Drugs 0.000 description 9
• 239000003814 drug Substances 0.000 description 9
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
• AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 8
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• 239000002775 capsule Substances 0.000 description 8
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• BPHQZTVXXXJVHI-UHFFFAOYSA-N dimyristoyl phosphatidylglycerol Chemical compound CCCCCCCCCCCCCC(=O)OCC(COP(O)(=O)OCC(O)CO)OC(=O)CCCCCCCCCCCCC BPHQZTVXXXJVHI-UHFFFAOYSA-N 0.000 description 8
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• 239000000969 carrier Substances 0.000 description 7
• SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 description 7
• 230000000694 effects Effects 0.000 description 7
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• VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 6
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
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