JP2011502134A5 - - Google Patents
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- JP2011502134A5 JP2011502134A5 JP2010531403A JP2010531403A JP2011502134A5 JP 2011502134 A5 JP2011502134 A5 JP 2011502134A5 JP 2010531403 A JP2010531403 A JP 2010531403A JP 2010531403 A JP2010531403 A JP 2010531403A JP 2011502134 A5 JP2011502134 A5 JP 2011502134A5
- Authority
- JP
- Japan
- Prior art keywords
- liposomes
- temperature
- liposome
- item
- active agent
- 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.)
- Granted
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- 239000002502 liposome Substances 0.000 claims description 212
- 239000013543 active substance Substances 0.000 claims description 51
- 239000002246 antineoplastic agent Substances 0.000 claims description 44
- 238000000034 method Methods 0.000 claims description 43
- 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 35
- 229960003668 docetaxel Drugs 0.000 claims description 31
- KILNVBDSWZSGLL-KXQOOQHDSA-N 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine Chemical group CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC KILNVBDSWZSGLL-KXQOOQHDSA-N 0.000 claims description 28
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 28
- 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 27
- 229960004562 carboplatin Drugs 0.000 claims description 26
- 239000008194 pharmaceutical composition Substances 0.000 claims description 25
- 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 24
- AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 claims description 24
- 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 24
- 239000002245 particle Substances 0.000 claims description 23
- 150000003904 phospholipids Chemical class 0.000 claims description 21
- 150000002632 lipids Chemical class 0.000 claims description 18
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- 230000007704 transition Effects 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 16
- 206010028980 Neoplasm Diseases 0.000 claims description 15
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- 229910052697 platinum Inorganic materials 0.000 claims description 14
- 230000000259 anti-tumor effect Effects 0.000 claims description 13
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- LVNGJLRDBYCPGB-UHFFFAOYSA-N 1,2-distearoylphosphatidylethanolamine Chemical class CCCCCCCCCCCCCCCCCC(=O)OCC(COP([O-])(=O)OCC[NH3+])OC(=O)CCCCCCCCCCCCCCCCC LVNGJLRDBYCPGB-UHFFFAOYSA-N 0.000 claims description 9
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- 239000002168 alkylating agent Substances 0.000 claims description 8
- 230000000340 anti-metabolite Effects 0.000 claims description 8
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- 239000003534 dna topoisomerase inhibitor Substances 0.000 claims description 8
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- 229940044693 topoisomerase inhibitor Drugs 0.000 claims description 8
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims description 7
- 229960004316 cisplatin Drugs 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- 229940123237 Taxane Drugs 0.000 claims description 6
- 230000003388 anti-hormonal effect Effects 0.000 claims description 6
- 230000006907 apoptotic process Effects 0.000 claims description 6
- 231100000433 cytotoxic Toxicity 0.000 claims description 6
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- 239000012634 fragment Substances 0.000 claims description 6
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- 239000003112 inhibitor Substances 0.000 claims description 5
- 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 5
- 230000008512 biological response Effects 0.000 claims description 4
- 239000003607 modifier Substances 0.000 claims description 4
- 150000004492 retinoid derivatives Chemical class 0.000 claims description 4
- 229940041181 antineoplastic drug Drugs 0.000 claims description 3
- 201000011510 cancer Diseases 0.000 claims description 3
- 230000001954 sterilising effect Effects 0.000 claims description 3
- 229930012538 Paclitaxel Natural products 0.000 claims description 2
- 229960005277 gemcitabine Drugs 0.000 claims description 2
- 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 2
- 229960001592 paclitaxel Drugs 0.000 claims description 2
- 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 2
- 239000006185 dispersion Substances 0.000 claims 6
- 190000008236 carboplatin Chemical compound 0.000 claims 5
- 239000007864 aqueous solution Substances 0.000 claims 2
- 230000000887 hydrating effect Effects 0.000 claims 2
- 239000002777 nucleoside Substances 0.000 claims 2
- 230000000717 retained effect Effects 0.000 claims 2
- 150000003833 nucleoside derivatives Chemical class 0.000 claims 1
- 125000003835 nucleoside group Chemical class 0.000 claims 1
- 239000003814 drug Substances 0.000 description 42
- 229940079593 drug Drugs 0.000 description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- YAYRGNWWLMLWJE-UHFFFAOYSA-L carboplatin Chemical compound O=C1O[Pt](N)(N)OC(=O)C11CCC1 YAYRGNWWLMLWJE-UHFFFAOYSA-L 0.000 description 21
- 210000001519 tissue Anatomy 0.000 description 17
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 241000699670 Mus sp. Species 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 229940088598 enzyme Drugs 0.000 description 9
- 241000196324 Embryophyta Species 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 229920001223 polyethylene glycol Polymers 0.000 description 8
- 238000005538 encapsulation Methods 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
- 239000002202 Polyethylene glycol Substances 0.000 description 6
- 239000003817 anthracycline antibiotic agent Substances 0.000 description 6
- 238000009826 distribution Methods 0.000 description 6
- 238000001727 in vivo Methods 0.000 description 6
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 5
- 241000699666 Mus <mouse, genus> Species 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
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- 239000008103 glucose Substances 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
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- 210000003205 muscle Anatomy 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- -1 BBR3464) Chemical compound 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 238000000113 differential scanning calorimetry Methods 0.000 description 4
- 238000009513 drug distribution Methods 0.000 description 4
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- 238000004458 analytical method Methods 0.000 description 3
- 238000000502 dialysis Methods 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 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 description 3
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- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- NHBKXEKEPDILRR-UHFFFAOYSA-N 2,3-bis(butanoylsulfanyl)propyl butanoate Chemical compound CCCC(=O)OCC(SC(=O)CCC)CSC(=O)CCC NHBKXEKEPDILRR-UHFFFAOYSA-N 0.000 description 2
- AOJJSUZBOXZQNB-VTZDEGQISA-N 4'-epidoxorubicin 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-VTZDEGQISA-N 0.000 description 2
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- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
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| US10349884B2 (en) | 2011-06-03 | 2019-07-16 | Sighpath Pharma Inc. | Liposomal mitigation of drug-induced inhibition of the cardiac ikr channel |
| US10238602B2 (en) | 2011-06-03 | 2019-03-26 | Signpath Pharma, Inc. | Protective effect of DMPC, DMPG, DMPC/DMPG, LysoPG and LysoPC against drugs that cause channelopathies |
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2007
- 2007-11-05 WO PCT/CN2007/003128 patent/WO2009059449A1/en not_active Ceased
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2008
- 2008-11-05 RU RU2010123009/15A patent/RU2497499C2/ru active
- 2008-11-05 WO PCT/CN2008/001846 patent/WO2009062398A1/en not_active Ceased
- 2008-11-05 BR BRPI0820505-1A patent/BRPI0820505A2/pt not_active Application Discontinuation
- 2008-11-05 CN CN2008801147881A patent/CN101883557B/zh not_active Expired - Fee Related
- 2008-11-05 MY MYPI20102010 patent/MY151268A/en unknown
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- 2008-11-05 KR KR1020107012248A patent/KR101652126B1/ko not_active Expired - Fee Related
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