JP2015533809A5 - - Google Patents
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- JP2015533809A5 JP2015533809A5 JP2015533122A JP2015533122A JP2015533809A5 JP 2015533809 A5 JP2015533809 A5 JP 2015533809A5 JP 2015533122 A JP2015533122 A JP 2015533122A JP 2015533122 A JP2015533122 A JP 2015533122A JP 2015533809 A5 JP2015533809 A5 JP 2015533809A5
- Authority
- JP
- Japan
- Prior art keywords
- acid
- therapeutic agent
- combination
- agent
- permeation enhancer
- 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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- 239000003814 drug Substances 0.000 claims 37
- 229940124597 therapeutic agent Drugs 0.000 claims 20
- 206010028980 Neoplasm Diseases 0.000 claims 19
- 230000003834 intracellular effect Effects 0.000 claims 19
- 239000003961 penetration enhancing agent Substances 0.000 claims 19
- -1 bevacizumab Chemical compound 0.000 claims 8
- 239000003795 chemical substances by application Substances 0.000 claims 7
- 230000001225 therapeutic effect Effects 0.000 claims 7
- 229960004316 cisplatin Drugs 0.000 claims 6
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims 6
- 201000011510 cancer Diseases 0.000 claims 5
- 238000009472 formulation Methods 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 239000000243 solution Substances 0.000 claims 4
- AIEMSTCGCMIJTI-UHFFFAOYSA-N 6-oxo-6-phenylhexanoic acid Chemical compound OC(=O)CCCCC(=O)C1=CC=CC=C1 AIEMSTCGCMIJTI-UHFFFAOYSA-N 0.000 claims 3
- 201000009030 Carcinoma Diseases 0.000 claims 3
- 206010039491 Sarcoma Diseases 0.000 claims 3
- 239000002246 antineoplastic agent Substances 0.000 claims 3
- 229940000425 combination drug Drugs 0.000 claims 3
- 150000001875 compounds Chemical group 0.000 claims 3
- 229940079593 drug Drugs 0.000 claims 3
- 230000002452 interceptive effect Effects 0.000 claims 3
- 229960005386 ipilimumab Drugs 0.000 claims 3
- WYWHKKSPHMUBEB-UHFFFAOYSA-N 6-Mercaptoguanine Natural products N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 claims 2
- RDRFZPRBCJRPCU-UHFFFAOYSA-N 8-cyclohexyl-8-oxooctanoic acid Chemical compound OC(=O)CCCCCCC(=O)C1CCCCC1 RDRFZPRBCJRPCU-UHFFFAOYSA-N 0.000 claims 2
- 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 claims 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 2
- FMRHJJZUHUTGKE-UHFFFAOYSA-N Ethylhexyl salicylate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1O FMRHJJZUHUTGKE-UHFFFAOYSA-N 0.000 claims 2
- NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 claims 2
- NAVMQTYZDKMPEU-UHFFFAOYSA-N Targretin Chemical compound CC1=CC(C(CCC2(C)C)(C)C)=C2C=C1C(=C)C1=CC=C(C(O)=O)C=C1 NAVMQTYZDKMPEU-UHFFFAOYSA-N 0.000 claims 2
- JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 claims 2
- RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 claims 2
- 229960000548 alemtuzumab Drugs 0.000 claims 2
- 229960000473 altretamine Drugs 0.000 claims 2
- 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 claims 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
- 229960000397 bevacizumab Drugs 0.000 claims 2
- 229960004562 carboplatin Drugs 0.000 claims 2
- 229960005395 cetuximab Drugs 0.000 claims 2
- 229940127089 cytotoxic agent Drugs 0.000 claims 2
- UUVWYPNAQBNQJQ-UHFFFAOYSA-N hexamethylmelamine Chemical compound CN(C)C1=NC(N(C)C)=NC(N(C)C)=N1 UUVWYPNAQBNQJQ-UHFFFAOYSA-N 0.000 claims 2
- 239000002955 immunomodulating agent Substances 0.000 claims 2
- 229960002450 ofatumumab Drugs 0.000 claims 2
- 229960001756 oxaliplatin Drugs 0.000 claims 2
- DWAFYCQODLXJNR-BNTLRKBRSA-L oxaliplatin Chemical compound O1C(=O)C(=O)O[Pt]11N[C@@H]2CCCC[C@H]2N1 DWAFYCQODLXJNR-BNTLRKBRSA-L 0.000 claims 2
- 229960001972 panitumumab Drugs 0.000 claims 2
- 229910052697 platinum Inorganic materials 0.000 claims 2
- 108090000623 proteins and genes Proteins 0.000 claims 2
- 102000004169 proteins and genes Human genes 0.000 claims 2
- 229960003087 tioguanine Drugs 0.000 claims 2
- MNRILEROXIRVNJ-UHFFFAOYSA-N tioguanine Chemical compound N1C(N)=NC(=S)C2=NC=N[C]21 MNRILEROXIRVNJ-UHFFFAOYSA-N 0.000 claims 2
- 229960005267 tositumomab Drugs 0.000 claims 2
- 229960000575 trastuzumab Drugs 0.000 claims 2
- 229960003048 vinblastine Drugs 0.000 claims 2
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 claims 2
- ZMEWRPBAQVSBBB-GOTSBHOMSA-N (2s)-2-[[(2s)-2-[(2-aminoacetyl)amino]-3-(4-hydroxyphenyl)propanoyl]amino]-6-[[2-[2-[2-[bis(carboxymethyl)amino]ethyl-(carboxymethyl)amino]ethyl-(carboxymethyl)amino]acetyl]amino]hexanoic acid Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CCN(CC(O)=O)CC(=O)NCCCC[C@@H](C(O)=O)NC(=O)[C@@H](NC(=O)CN)CC1=CC=C(O)C=C1 ZMEWRPBAQVSBBB-GOTSBHOMSA-N 0.000 claims 1
- DEQANNDTNATYII-OULOTJBUSA-N (4r,7s,10s,13r,16s,19r)-10-(4-aminobutyl)-19-[[(2r)-2-amino-3-phenylpropanoyl]amino]-16-benzyl-n-[(2r,3r)-1,3-dihydroxybutan-2-yl]-7-[(1r)-1-hydroxyethyl]-13-(1h-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carboxa Chemical compound C([C@@H](N)C(=O)N[C@H]1CSSC[C@H](NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](CC=2C3=CC=CC=C3NC=2)NC(=O)[C@H](CC=2C=CC=CC=2)NC1=O)C(=O)N[C@H](CO)[C@H](O)C)C1=CC=CC=C1 DEQANNDTNATYII-OULOTJBUSA-N 0.000 claims 1
- FPVKHBSQESCIEP-UHFFFAOYSA-N (8S)-3-(2-deoxy-beta-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol Natural products C1C(O)C(CO)OC1N1C(NC=NCC2O)=C2N=C1 FPVKHBSQESCIEP-UHFFFAOYSA-N 0.000 claims 1
- FDKXTQMXEQVLRF-ZHACJKMWSA-N (E)-dacarbazine Chemical compound CN(C)\N=N\c1[nH]cnc1C(N)=O FDKXTQMXEQVLRF-ZHACJKMWSA-N 0.000 claims 1
- HJTAZXHBEBIQQX-UHFFFAOYSA-N 1,5-bis(chloromethyl)naphthalene Chemical compound C1=CC=C2C(CCl)=CC=CC2=C1CCl HJTAZXHBEBIQQX-UHFFFAOYSA-N 0.000 claims 1
- VSNHCAURESNICA-NJFSPNSNSA-N 1-oxidanylurea Chemical compound N[14C](=O)NO VSNHCAURESNICA-NJFSPNSNSA-N 0.000 claims 1
- UEJJHQNACJXSKW-UHFFFAOYSA-N 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C1CCC(=O)NC1=O UEJJHQNACJXSKW-UHFFFAOYSA-N 0.000 claims 1
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims 1
- RTQWWZBSTRGEAV-PKHIMPSTSA-N 2-[[(2s)-2-[bis(carboxymethyl)amino]-3-[4-(methylcarbamoylamino)phenyl]propyl]-[2-[bis(carboxymethyl)amino]propyl]amino]acetic acid Chemical compound CNC(=O)NC1=CC=C(C[C@@H](CN(CC(C)N(CC(O)=O)CC(O)=O)CC(O)=O)N(CC(O)=O)CC(O)=O)C=C1 RTQWWZBSTRGEAV-PKHIMPSTSA-N 0.000 claims 1
- IIWOLBQTYSVLNZ-UHFFFAOYSA-N 3-(3-methylcyclohexyl)oxypropanoic acid Chemical compound CC1CCCC(OCCC(O)=O)C1 IIWOLBQTYSVLNZ-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- QGCYUEIWRLWOSH-UHFFFAOYSA-N 4-(3-methylcyclohexyl)oxybutanoic acid Chemical compound CC1CCCC(OCCCC(O)=O)C1 QGCYUEIWRLWOSH-UHFFFAOYSA-N 0.000 claims 1
- YFJPWCSWYQDNGQ-UHFFFAOYSA-N 4-cyclobutyl-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)C1CCC1 YFJPWCSWYQDNGQ-UHFFFAOYSA-N 0.000 claims 1
- LOVFEGLWBFHQLB-UHFFFAOYSA-N 4-cyclopentyl-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)C1CCCC1 LOVFEGLWBFHQLB-UHFFFAOYSA-N 0.000 claims 1
- ISZLFKWEBSKHTO-UHFFFAOYSA-N 4-cyclopropyl-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)C1CC1 ISZLFKWEBSKHTO-UHFFFAOYSA-N 0.000 claims 1
- AWQSAIIDOMEEOD-UHFFFAOYSA-N 5,5-Dimethyl-4-(3-oxobutyl)dihydro-2(3H)-furanone Chemical compound CC(=O)CCC1CC(=O)OC1(C)C AWQSAIIDOMEEOD-UHFFFAOYSA-N 0.000 claims 1
- YQKCZJRLIOVJPZ-UHFFFAOYSA-N 5-(3-methylcyclohexyl)oxypentanoic acid Chemical compound CC1CCCC(OCCCCC(O)=O)C1 YQKCZJRLIOVJPZ-UHFFFAOYSA-N 0.000 claims 1
- NMUSYJAQQFHJEW-KVTDHHQDSA-N 5-azacytidine Chemical compound O=C1N=C(N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 NMUSYJAQQFHJEW-KVTDHHQDSA-N 0.000 claims 1
- BRBJICIEJBXXJQ-UHFFFAOYSA-N 5-cyclobutyl-5-oxopentanoic acid Chemical compound OC(=O)CCCC(=O)C1CCC1 BRBJICIEJBXXJQ-UHFFFAOYSA-N 0.000 claims 1
- FEHBUZYBKUOFIA-UHFFFAOYSA-N 5-cyclohexyl-5-oxopentanoic acid Chemical compound OC(=O)CCCC(=O)C1CCCCC1 FEHBUZYBKUOFIA-UHFFFAOYSA-N 0.000 claims 1
- DRLJGCXABGDQMI-UHFFFAOYSA-N 5-cyclopentyl-5-oxopentanoic acid Chemical compound OC(=O)CCCC(=O)C1CCCC1 DRLJGCXABGDQMI-UHFFFAOYSA-N 0.000 claims 1
- GHDNXBQUOFVFDF-UHFFFAOYSA-N 5-cyclopropyl-5-oxopentanoic acid Chemical compound OC(=O)CCCC(=O)C1CC1 GHDNXBQUOFVFDF-UHFFFAOYSA-N 0.000 claims 1
- ZLISLBQFNDTLMV-UHFFFAOYSA-N 6-(3-methylcyclohexyl)oxyhexanoic acid Chemical compound CC1CCCC(OCCCCCC(O)=O)C1 ZLISLBQFNDTLMV-UHFFFAOYSA-N 0.000 claims 1
- NIRYFHPBAWKZBA-UHFFFAOYSA-N 6-cyclobutyl-6-oxohexanoic acid Chemical compound OC(=O)CCCCC(=O)C1CCC1 NIRYFHPBAWKZBA-UHFFFAOYSA-N 0.000 claims 1
- ITWAGYWPYYIURG-UHFFFAOYSA-N 6-cyclohexyl-6-oxohexanoic acid Chemical compound OC(=O)CCCCC(=O)C1CCCCC1 ITWAGYWPYYIURG-UHFFFAOYSA-N 0.000 claims 1
- IMEXAZLWJSUWAX-UHFFFAOYSA-N 6-cyclopentyl-6-oxohexanoic acid Chemical compound OC(=O)CCCCC(=O)C1CCCC1 IMEXAZLWJSUWAX-UHFFFAOYSA-N 0.000 claims 1
- CYYSWLBWCYNGQX-UHFFFAOYSA-N 6-cyclopropyl-6-oxohexanoic acid Chemical compound OC(=O)CCCCC(=O)C1CC1 CYYSWLBWCYNGQX-UHFFFAOYSA-N 0.000 claims 1
- 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 1
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- KPYUQMVVPZHXIK-UHFFFAOYSA-N 7-cyclohexyl-7-oxoheptanoic acid Chemical compound OC(=O)CCCCCC(=O)C1CCCCC1 KPYUQMVVPZHXIK-UHFFFAOYSA-N 0.000 claims 1
- NCMFHVOZSIOSMD-UHFFFAOYSA-N 7-cyclopentyl-7-oxoheptanoic acid Chemical compound OC(=O)CCCCCC(=O)C1CCCC1 NCMFHVOZSIOSMD-UHFFFAOYSA-N 0.000 claims 1
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- XRTHAPZDZPADIL-UHFFFAOYSA-N 8-[(5-chloro-2-hydroxybenzoyl)amino]octanoic acid Chemical compound OC(=O)CCCCCCCNC(=O)C1=CC(Cl)=CC=C1O XRTHAPZDZPADIL-UHFFFAOYSA-N 0.000 claims 1
- PFFDQUOOAOYQHO-UHFFFAOYSA-N 8-cyclobutyl-8-oxooctanoic acid Chemical compound OC(=O)CCCCCCC(=O)C1CCC1 PFFDQUOOAOYQHO-UHFFFAOYSA-N 0.000 claims 1
- QVTINBMJKAORHL-UHFFFAOYSA-N 8-cyclopentyl-8-oxooctanoic acid Chemical compound OC(=O)CCCCCCC(=O)C1CCCC1 QVTINBMJKAORHL-UHFFFAOYSA-N 0.000 claims 1
- KQOVMVZQORRTLN-UHFFFAOYSA-N 8-cyclopropyl-8-oxooctanoic acid Chemical compound OC(=O)CCCCCCC(=O)C1CC1 KQOVMVZQORRTLN-UHFFFAOYSA-N 0.000 claims 1
- UMCSRRHQLAVYRS-UHFFFAOYSA-N 8-oxo-8-phenyloctanoic acid Chemical compound OC(=O)CCCCCCC(=O)C1=CC=CC=C1 UMCSRRHQLAVYRS-UHFFFAOYSA-N 0.000 claims 1
- SHGAZHPCJJPHSC-ZVCIMWCZSA-N 9-cis-retinoic acid Chemical compound OC(=O)/C=C(\C)/C=C/C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-ZVCIMWCZSA-N 0.000 claims 1
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- 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 1
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- BLCLNMBMMGCOAS-URPVMXJPSA-N Goserelin Chemical compound C([C@@H](C(=O)N[C@H](COC(C)(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N1[C@@H](CCC1)C(=O)NNC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H]1NC(=O)CC1)C1=CC=C(O)C=C1 BLCLNMBMMGCOAS-URPVMXJPSA-N 0.000 claims 1
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