JP2011225614A5

JP2011225614A5 -

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Publication number: JP2011225614A5
Authority: JP; Japan
Prior art keywords: hydrogen; pharmaceutical composition; cancer; composition according; alkyl
Prior art date: 2011-08-04
Legal status : Granted

Application number

JP2011170747A

Other languages

English (en)

Japanese (ja)

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JP2011225614A (ja

JP5313308B2 (ja

Filing date

2011-08-04

Publication date

2012-04-05

2011-08-04 Application filed filed Critical

2011-11-10 Publication of JP2011225614A publication Critical patent/JP2011225614A/ja

2012-04-05 Publication of JP2011225614A5 publication Critical patent/JP2011225614A5/ja

2013-10-09 Application granted granted Critical

2013-10-09 Publication of JP5313308B2 publication Critical patent/JP5313308B2/ja

2024-12-23 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

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229910052739 hydrogen Inorganic materials 0.000 claims description 336
239000001257 hydrogen Substances 0.000 claims description 326
150000001875 compounds Chemical class 0.000 claims description 253
150000002431 hydrogen Chemical class 0.000 claims description 236
125000000217 alkyl group Chemical group 0.000 claims description 219
239000000203 mixture Substances 0.000 claims description 172
125000003710 aryl alkyl group Chemical group 0.000 claims description 170
125000000753 cycloalkyl group Chemical group 0.000 claims description 157
125000004475 heteroaralkyl group Chemical group 0.000 claims description 143
125000003118 aryl group Chemical group 0.000 claims description 134
125000001072 heteroaryl group Chemical group 0.000 claims description 134
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 125
150000003839 salts Chemical class 0.000 claims description 108
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 104
125000003342 alkenyl group Chemical group 0.000 claims description 98
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 90
125000000304 alkynyl group Chemical group 0.000 claims description 88
-1 ethylenediaminetetraacetic acid disodium calcium acetate dihydrate Chemical group 0.000 claims description 72
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 64
239000008194 pharmaceutical composition Substances 0.000 claims description 59
125000003545 alkoxy group Chemical group 0.000 claims description 41
125000004442 acylamino group Chemical group 0.000 claims description 40
125000000623 heterocyclic group Chemical group 0.000 claims description 39
150000004820 halides Chemical class 0.000 claims description 37
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical group OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 36
239000002246 antineoplastic agent Substances 0.000 claims description 36
206010028980 Neoplasm Diseases 0.000 claims description 35
235000010323 ascorbic acid Nutrition 0.000 claims description 33
239000011668 ascorbic acid Substances 0.000 claims description 33
239000000872 buffer Substances 0.000 claims description 32
201000011510 cancer Diseases 0.000 claims description 32
238000011282 treatment Methods 0.000 claims description 31
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 30
239000003963 antioxidant agent Substances 0.000 claims description 27
235000006708 antioxidants Nutrition 0.000 claims description 27
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 26
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 26
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 26
125000003282 alkyl amino group Chemical group 0.000 claims description 25
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 25
125000004423 acyloxy group Chemical group 0.000 claims description 24
125000005035 acylthio group Chemical group 0.000 claims description 24
125000001691 aryl alkyl amino group Chemical group 0.000 claims description 24
125000001769 aryl amino group Chemical group 0.000 claims description 24
125000004104 aryloxy group Chemical group 0.000 claims description 24
229960005070 ascorbic acid Drugs 0.000 claims description 24
150000002825 nitriles Chemical class 0.000 claims description 24
SOWBFZRMHSNYGE-UHFFFAOYSA-N Monoamide-Oxalic acid Natural products NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 claims description 23
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 22
229910052751 metal Inorganic materials 0.000 claims description 22
239000002184 metal Substances 0.000 claims description 22
239000002738 chelating agent Substances 0.000 claims description 21
230000003078 antioxidant effect Effects 0.000 claims description 19
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 16
ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 16
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 15
150000001539 azetidines Chemical class 0.000 claims description 15
HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 claims description 15
KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 claims description 15
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 15
AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 claims description 13
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 13
ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 12
229940077388 benzenesulfonate Drugs 0.000 claims description 12
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims description 12
229940109275 cyclamate Drugs 0.000 claims description 12
229940072107 ascorbate Drugs 0.000 claims description 11
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical group [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 10
229960000846 camphor Drugs 0.000 claims description 7
MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 claims description 7
206010006187 Breast cancer Diseases 0.000 claims description 6
208000026310 Breast neoplasm Diseases 0.000 claims description 6
206010009944 Colon cancer Diseases 0.000 claims description 6
229930012538 Paclitaxel Natural products 0.000 claims description 6
206010060862 Prostate cancer Diseases 0.000 claims description 6
208000000236 Prostatic Neoplasms Diseases 0.000 claims description 6
125000003289 ascorbyl group Chemical group [H]O[C@@]([H])(C([H])([H])O*)[C@@]1([H])OC(=O)C(O*)=C1O* 0.000 claims description 6
GXJABQQUPOEUTA-RDJZCZTQSA-N bortezomib Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)B(O)O)NC(=O)C=1N=CC=NC=1)C1=CC=CC=C1 GXJABQQUPOEUTA-RDJZCZTQSA-N 0.000 claims description 6
229960001592 paclitaxel Drugs 0.000 claims description 6
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 6
208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 5
208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims description 5
208000010833 Chronic myeloid leukaemia Diseases 0.000 claims description 5
208000034578 Multiple myelomas Diseases 0.000 claims description 5
208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims description 5
208000033776 Myeloid Acute Leukemia Diseases 0.000 claims description 5
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 5
206010033128 Ovarian cancer Diseases 0.000 claims description 5
206010061535 Ovarian neoplasm Diseases 0.000 claims description 5
206010035226 Plasma cell myeloma Diseases 0.000 claims description 5
229960003668 docetaxel Drugs 0.000 claims description 5
201000001441 melanoma Diseases 0.000 claims description 5
206010058467 Lung neoplasm malignant Diseases 0.000 claims description 4
208000029742 colonic neoplasm Diseases 0.000 claims description 4
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 4
229960005277 gemcitabine Drugs 0.000 claims description 4
229960003685 imatinib mesylate Drugs 0.000 claims description 4
YLMAHDNUQAMNNX-UHFFFAOYSA-N imatinib methanesulfonate Chemical compound CS(O)(=O)=O.C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 YLMAHDNUQAMNNX-UHFFFAOYSA-N 0.000 claims description 4
201000005202 lung cancer Diseases 0.000 claims description 4
208000020816 lung neoplasm Diseases 0.000 claims description 4
238000001959 radiotherapy Methods 0.000 claims description 4
208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims description 2
208000014697 Acute lymphocytic leukaemia Diseases 0.000 claims description 2
208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims description 2
206010005003 Bladder cancer Diseases 0.000 claims description 2
208000003174 Brain Neoplasms Diseases 0.000 claims description 2
206010008342 Cervix carcinoma Diseases 0.000 claims description 2
208000001333 Colorectal Neoplasms Diseases 0.000 claims description 2
GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims description 2
208000017604 Hodgkin disease Diseases 0.000 claims description 2
208000021519 Hodgkin lymphoma Diseases 0.000 claims description 2
208000010747 Hodgkins lymphoma Diseases 0.000 claims description 2
208000008839 Kidney Neoplasms Diseases 0.000 claims description 2
239000002211 L-ascorbic acid Substances 0.000 claims description 2
235000000069 L-ascorbic acid Nutrition 0.000 claims description 2
208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims description 2
201000003793 Myelodysplastic syndrome Diseases 0.000 claims description 2
208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims description 2
206010061902 Pancreatic neoplasm Diseases 0.000 claims description 2
208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims description 2
206010038389 Renal cancer Diseases 0.000 claims description 2
208000006265 Renal cell carcinoma Diseases 0.000 claims description 2
208000024770 Thyroid neoplasm Diseases 0.000 claims description 2
208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 2
208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims description 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 description 2
229960004562 carboplatin Drugs 0.000 claims description 2
201000010881 cervical cancer Diseases 0.000 claims description 2
208000032852 chronic lymphocytic leukemia Diseases 0.000 claims description 2
DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims description 2
229960004316 cisplatin Drugs 0.000 claims description 2
208000035250 cutaneous malignant susceptibility to 1 melanoma Diseases 0.000 claims description 2
229960002949 fluorouracil Drugs 0.000 claims description 2
201000010536 head and neck cancer Diseases 0.000 claims description 2
208000014829 head and neck neoplasm Diseases 0.000 claims description 2
201000010982 kidney cancer Diseases 0.000 claims description 2
208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 2
208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 2
201000002528 pancreatic cancer Diseases 0.000 claims description 2
208000008443 pancreatic carcinoma Diseases 0.000 claims description 2
201000002510 thyroid cancer Diseases 0.000 claims description 2
208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 2
201000005112 urinary bladder cancer Diseases 0.000 claims description 2
206010041067 Small cell lung cancer Diseases 0.000 claims 2
229960001467 bortezomib Drugs 0.000 claims 2
208000000587 small cell lung carcinoma Diseases 0.000 claims 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 173
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 138
238000000034 method Methods 0.000 description 125
239000000243 solution Substances 0.000 description 119
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 113
AYUNIORJHRXIBJ-TXHRRWQRSA-N tanespimycin Chemical compound N1C(=O)\C(C)=C\C=C/[C@H](OC)[C@@H](OC(N)=O)\C(C)=C\[C@H](C)[C@@H](O)[C@@H](OC)C[C@H](C)CC2=C(NCC=C)C(=O)C=C1C2=O AYUNIORJHRXIBJ-TXHRRWQRSA-N 0.000 description 110
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 107
235000002639 sodium chloride Nutrition 0.000 description 105
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 74
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 72
239000012044 organic layer Substances 0.000 description 67
229910052757 nitrogen Inorganic materials 0.000 description 64
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 64
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 63
239000002253 acid Substances 0.000 description 56
229910052760 oxygen Inorganic materials 0.000 description 47
235000019439 ethyl acetate Nutrition 0.000 description 45
239000001301 oxygen Substances 0.000 description 45
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 44
238000002360 preparation method Methods 0.000 description 39
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JRZJKWGQFNTSRN-UHFFFAOYSA-N Geldanamycin Natural products C1C(C)CC(OC)C(O)C(C)C=C(C)C(OC(N)=O)C(OC)CCC=C(C)C(=O)NC2=CC(=O)C(OC)=C1C2=O JRZJKWGQFNTSRN-UHFFFAOYSA-N 0.000 description 38
QTQAWLPCGQOSGP-GBTDJJJQSA-N geldanamycin Chemical compound N1C(=O)\C(C)=C/C=C\[C@@H](OC)[C@H](OC(N)=O)\C(C)=C/[C@@H](C)[C@@H](O)[C@H](OC)C[C@@H](C)CC2=C(OC)C(=O)C=C1C2=O QTQAWLPCGQOSGP-GBTDJJJQSA-N 0.000 description 38
239000007864 aqueous solution Substances 0.000 description 36
JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 36
239000010410 layer Substances 0.000 description 35
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 34
238000006243 chemical reaction Methods 0.000 description 33
230000002829 reductive effect Effects 0.000 description 33
239000003814 drug Substances 0.000 description 30
150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 29
238000001819 mass spectrum Methods 0.000 description 28
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 26
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
238000009472 formulation Methods 0.000 description 25
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
229960004106 citric acid Drugs 0.000 description 24
235000015165 citric acid Nutrition 0.000 description 24
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 22
239000012267 brine Substances 0.000 description 22
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 22
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 22
101710113864 Heat shock protein 90 Proteins 0.000 description 21
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229910052717 sulfur Chemical group 0.000 description 21
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238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 19
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ATEBXHFBFRCZMA-VXTBVIBXSA-N rifabutin Chemical compound O([C@](C1=O)(C)O/C=C/[C@@H]([C@H]([C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(C)/C(=O)NC(=C2N3)C(=O)C=4C(O)=C5C)C)OC)C5=C1C=4C2=NC13CCN(CC(C)C)CC1 ATEBXHFBFRCZMA-VXTBVIBXSA-N 0.000 description 19
239000011593 sulfur Chemical group 0.000 description 19
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 18
229960000885 rifabutin Drugs 0.000 description 18
125000001424 substituent group Chemical group 0.000 description 18
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QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
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BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 14
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 14
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WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 13
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125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 12
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FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 11
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230000005855 radiation Effects 0.000 description 11
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 10
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 10
125000002252 acyl group Chemical group 0.000 description 10
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JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 9
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
239000004471 Glycine Substances 0.000 description 9
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JP2011170747A 2003-12-23 2011-08-04 癌治療に使用するベンゾキノン包含アンサマイシン類のアナログ Expired - Fee Related JP5313308B2 (ja)