JP2018528257A5 - - Google Patents

Info

Publication number

JP2018528257A5

JP2018528257A5 JP2018521190A JP2018521190A JP2018528257A5 JP 2018528257 A5 JP2018528257 A5 JP 2018528257A5 JP 2018521190 A JP2018521190 A JP 2018521190A JP 2018521190 A JP2018521190 A JP 2018521190A JP 2018528257 A5 JP2018528257 A5 JP 2018528257A5

Authority

JP

Japan

Prior art keywords

seq

group

amino acid

terminus

peptide

Prior art date

2016-07-08

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.)

Pending

Links

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• 150000001413 amino acids Chemical class 0.000 claims description 110
• 108090000765 processed proteins & peptides Proteins 0.000 claims description 57
• 239000000203 mixture Substances 0.000 claims description 29
• 125000003275 alpha amino acid group Chemical group 0.000 claims description 21
• 102000004196 processed proteins & peptides Human genes 0.000 claims description 13
• 244000137850 Marrubium vulgare Species 0.000 claims description 10
• 150000003904 phospholipids Chemical class 0.000 claims description 10
• 239000003795 chemical substances by application Substances 0.000 claims description 7
• 150000002632 lipids Chemical class 0.000 claims description 7
• HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical group C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 6
• 229940079593 drug Drugs 0.000 claims description 6
• 239000003814 drug Substances 0.000 claims description 6
• 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 6
• OTXNTMVVOOBZCV-UHFFFAOYSA-N 2R-gamma-tocotrienol Chemical group OC1=C(C)C(C)=C2OC(CCC=C(C)CCC=C(C)CCC=C(C)C)(C)CCC2=C1 OTXNTMVVOOBZCV-UHFFFAOYSA-N 0.000 claims description 5
• 125000003277 amino group Chemical group 0.000 claims description 5
• 210000004899 c-terminal region Anatomy 0.000 claims description 5
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
• -1 polyethylene Polymers 0.000 claims description 5
• 229930012538 Paclitaxel Natural products 0.000 claims description 4
• RZFHLOLGZPDCHJ-DLQZEEBKSA-N alpha-Tocotrienol Chemical group Oc1c(C)c(C)c2O[C@@](CC/C=C(/CC/C=C(\CC/C=C(\C)/C)/C)\C)(C)CCc2c1C RZFHLOLGZPDCHJ-DLQZEEBKSA-N 0.000 claims description 4
• 239000002246 antineoplastic agent Substances 0.000 claims description 4
• 229940041181 antineoplastic drug Drugs 0.000 claims description 4
• 229960001592 paclitaxel Drugs 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
• ODADKLYLWWCHNB-UHFFFAOYSA-N 2R-delta-tocotrienol Chemical group OC1=CC(C)=C2OC(CCC=C(C)CCC=C(C)CCC=C(C)C)(C)CCC2=C1 ODADKLYLWWCHNB-UHFFFAOYSA-N 0.000 claims description 3
• STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 claims description 3
• 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
• 235000012000 cholesterol Nutrition 0.000 claims description 3
• 150000001875 compounds Chemical class 0.000 claims description 3
• STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin 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(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 claims description 3
• 229960000975 daunorubicin Drugs 0.000 claims description 3
• BTNBMQIHCRIGOU-UHFFFAOYSA-N delta-tocotrienol Chemical group CC(=CCCC(=CCCC(=CCCOC1(C)CCc2cc(O)cc(C)c2O1)C)C)C BTNBMQIHCRIGOU-UHFFFAOYSA-N 0.000 claims description 3
• 229960003668 docetaxel Drugs 0.000 claims description 3
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
• 239000011729 δ-tocotrienol Chemical group 0.000 claims description 3
• 235000019144 δ-tocotrienol Nutrition 0.000 claims description 3
• ODADKLYLWWCHNB-LDYBVBFYSA-N δ-tocotrienol Chemical group OC1=CC(C)=C2O[C@@](CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)(C)CCC2=C1 ODADKLYLWWCHNB-LDYBVBFYSA-N 0.000 claims description 3
• FGYKUFVNYVMTAM-UHFFFAOYSA-N (R)-2,5,8-trimethyl-2-(4,8,12-trimethyl-trideca-3t,7t,11-trienyl)-chroman-6-ol Chemical group OC1=CC(C)=C2OC(CCC=C(C)CCC=C(C)CCC=C(C)C)(C)CCC2=C1C FGYKUFVNYVMTAM-UHFFFAOYSA-N 0.000 claims description 2
• TZCPCKNHXULUIY-RGULYWFUSA-N 1,2-distearoyl-sn-glycero-3-phosphoserine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCCCCCCCCCCC TZCPCKNHXULUIY-RGULYWFUSA-N 0.000 claims description 2
• HAWSQZCWOQZXHI-FQEVSTJZSA-N 10-Hydroxycamptothecin Chemical compound C1=C(O)C=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 HAWSQZCWOQZXHI-FQEVSTJZSA-N 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
• ZWZWYGMENQVNFU-UHFFFAOYSA-N Glycerophosphorylserin Natural products OC(=O)C(N)COP(O)(=O)OCC(O)CO ZWZWYGMENQVNFU-UHFFFAOYSA-N 0.000 claims description 2
• 239000004698 Polyethylene Substances 0.000 claims description 2
• 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 2
• 229940064063 alpha tocotrienol Drugs 0.000 claims description 2
• AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 claims description 2
• FGYKUFVNYVMTAM-YMCDKREISA-N beta-Tocotrienol Chemical group Oc1c(C)c2c(c(C)c1)O[C@@](CC/C=C(\CC/C=C(\CC/C=C(\C)/C)/C)/C)(C)CC2 FGYKUFVNYVMTAM-YMCDKREISA-N 0.000 claims description 2
• ZGSPNIOCEDOHGS-UHFFFAOYSA-L disodium [3-[2,3-di(octadeca-9,12-dienoyloxy)propoxy-oxidophosphoryl]oxy-2-hydroxypropyl] 2,3-di(octadeca-9,12-dienoyloxy)propyl phosphate Chemical compound [Na+].[Na+].CCCCCC=CCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCC=CCCCCC)COP([O-])(=O)OCC(O)COP([O-])(=O)OCC(OC(=O)CCCCCCCC=CCC=CCCCCC)COC(=O)CCCCCCCC=CCC=CCCCCC ZGSPNIOCEDOHGS-UHFFFAOYSA-L 0.000 claims description 2
• FGYKUFVNYVMTAM-MUUNZHRXSA-N epsilon-Tocopherol Chemical group OC1=CC(C)=C2O[C@@](CCC=C(C)CCC=C(C)CCC=C(C)C)(C)CCC2=C1C FGYKUFVNYVMTAM-MUUNZHRXSA-N 0.000 claims description 2
• OTXNTMVVOOBZCV-YMCDKREISA-N gamma-Tocotrienol Chemical group Oc1c(C)c(C)c2O[C@@](CC/C=C(\CC/C=C(\CC/C=C(\C)/C)/C)/C)(C)CCc2c1 OTXNTMVVOOBZCV-YMCDKREISA-N 0.000 claims description 2
• 150000008104 phosphatidylethanolamines Chemical class 0.000 claims description 2
• 150000003905 phosphatidylinositols Chemical class 0.000 claims description 2
• 229920000573 polyethylene Polymers 0.000 claims description 2
• RZFHLOLGZPDCHJ-XZXLULOTSA-N α-Tocotrienol Chemical group OC1=C(C)C(C)=C2O[C@@](CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)(C)CCC2=C1C RZFHLOLGZPDCHJ-XZXLULOTSA-N 0.000 claims description 2
• 239000011730 α-tocotrienol Chemical group 0.000 claims description 2
• 235000019145 α-tocotrienol Nutrition 0.000 claims description 2
• 239000011723 β-tocotrienol Chemical group 0.000 claims description 2
• 235000019151 β-tocotrienol Nutrition 0.000 claims description 2
• FGYKUFVNYVMTAM-WAZJVIJMSA-N β-tocotrienol Chemical group OC1=CC(C)=C2O[C@@](CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)(C)CCC2=C1C FGYKUFVNYVMTAM-WAZJVIJMSA-N 0.000 claims description 2
• 239000011722 γ-tocotrienol Chemical group 0.000 claims description 2
• 235000019150 γ-tocotrienol Nutrition 0.000 claims description 2
• OTXNTMVVOOBZCV-WAZJVIJMSA-N γ-tocotrienol Chemical group OC1=C(C)C(C)=C2O[C@@](CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)(C)CCC2=C1 OTXNTMVVOOBZCV-WAZJVIJMSA-N 0.000 claims description 2
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 2
• FWMNVWWHGCHHJJ-SKKKGAJSSA-N 4-amino-1-[(2r)-6-amino-2-[[(2r)-2-[[(2r)-2-[[(2r)-2-amino-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoyl]amino]hexanoyl]piperidine-4-carboxylic acid Chemical compound C([C@H](C(=O)N[C@H](CC(C)C)C(=O)N[C@H](CCCCN)C(=O)N1CCC(N)(CC1)C(O)=O)NC(=O)[C@H](N)CC=1C=CC=CC=1)C1=CC=CC=C1 FWMNVWWHGCHHJJ-SKKKGAJSSA-N 0.000 claims 1
• 239000013543 active substance Substances 0.000 claims 1
• JWXLCQHWBFHMOI-NIQMUPOESA-N bis[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] carbonate Chemical compound C([C@@H]12)C[C@]3(C)[C@@H]([C@H](C)CCCC(C)C)CC[C@H]3[C@@H]1CC=C(C1)[C@]2(C)CC[C@@H]1OC(=O)O[C@@H]1CC2=CC[C@H]3[C@@H]4CC[C@H]([C@H](C)CCCC(C)C)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC1 JWXLCQHWBFHMOI-NIQMUPOESA-N 0.000 claims 1
• 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 1
• 229960005277 gemcitabine Drugs 0.000 claims 1
• 239000002872 contrast media Substances 0.000 description 6
• 238000000034 method Methods 0.000 description 4
• 201000010099 disease Diseases 0.000 description 3
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
• 239000011572 manganese Substances 0.000 description 2
• 229960003330 pentetic acid Drugs 0.000 description 2
• OBPOCAKICKFMGM-PGUFJCEWSA-N 2-[di(hexadecanoyl)amino]ethyl [(2R)-2,3-dihydroxypropyl] hydrogen phosphate Chemical group C(CCCCCCCCCCCCCCC)(=O)N(CCOP(OC[C@@H](CO)O)(=O)O)C(CCCCCCCCCCCCCCC)=O OBPOCAKICKFMGM-PGUFJCEWSA-N 0.000 description 1
• AKJHMTWEGVYYSE-AIRMAKDCSA-N 4-HPR Chemical compound C=1C=C(O)C=CC=1NC(=O)/C=C(\C)/C=C/C=C(C)C=CC1=C(C)CCCC1(C)C AKJHMTWEGVYYSE-AIRMAKDCSA-N 0.000 description 1
• 229910052688 Gadolinium Inorganic materials 0.000 description 1
• 206010028980 Neoplasm Diseases 0.000 description 1
• 239000002253 acid Substances 0.000 description 1
• 230000010933 acylation Effects 0.000 description 1
• 238000005917 acylation reaction Methods 0.000 description 1
• 201000011510 cancer Diseases 0.000 description 1
• LRCTTYSATZVTRI-UHFFFAOYSA-L cyclohexane-1,2-diamine;platinum(4+);tetradecanoate Chemical compound [Pt+4].NC1CCCCC1N.CCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCC([O-])=O LRCTTYSATZVTRI-UHFFFAOYSA-L 0.000 description 1
• 229950003662 fenretinide Drugs 0.000 description 1
• 229910052748 manganese Inorganic materials 0.000 description 1
• 239000000693 micelle Substances 0.000 description 1
• 229950004962 miriplatin Drugs 0.000 description 1