SK280864B6 - Acridine derivatives, process for their preparation, and pharmaceutical compositions based thereon - Google Patents

Info

Publication number

SK280864B6

SK280864B6 SK730-93A SK73093A SK280864B6 SK 280864 B6 SK280864 B6 SK 280864B6 SK 73093 A SK73093 A SK 73093A SK 280864 B6 SK280864 B6 SK 280864B6

Authority

SK

Slovakia

Prior art keywords

dihydro

oxo

methyl

phenyl

acridinecarboxamide

Prior art date

1991-01-11

Links

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• Global Dossier
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• 238000000034 method Methods 0.000 title claims abstract description 26
• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 21
• 229940027998 antiseptic and disinfectant acridine derivative Drugs 0.000 title claims abstract description 10
• 230000008569 process Effects 0.000 title claims abstract description 8
• 125000000641 acridinyl group Chemical class C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 title claims abstract 4
• 238000002360 preparation method Methods 0.000 title abstract description 7
• 150000001875 compounds Chemical class 0.000 claims abstract description 326
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 73
• 239000002246 antineoplastic agent Substances 0.000 claims abstract description 35
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 34
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 27
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 13
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 12
• 239000001301 oxygen Substances 0.000 claims abstract description 10
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 5
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 3
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 3
• 238000002560 therapeutic procedure Methods 0.000 claims abstract 2
• 239000000203 mixture Substances 0.000 claims description 247
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 175
• -1 1,2,3,4-tetrahydro-6,7-dimethoxy-2-isoquinolinyl Chemical group 0.000 claims description 170
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 120
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 54
• 229910052739 hydrogen Inorganic materials 0.000 claims description 49
• 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 46
• 239000001257 hydrogen Substances 0.000 claims description 44
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 41
• 150000003839 salts Chemical class 0.000 claims description 40
• 239000000126 substance Substances 0.000 claims description 34
• UWRRBLDAEWEWRC-UHFFFAOYSA-N 9-oxo-10h-acridine-4-carboxamide Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C(C(=O)N)=CC=C2 UWRRBLDAEWEWRC-UHFFFAOYSA-N 0.000 claims description 30
• 239000012453 solvate Substances 0.000 claims description 28
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 27
• 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 27
• 150000002431 hydrogen Chemical class 0.000 claims description 23
• 206010028980 Neoplasm Diseases 0.000 claims description 22
• 125000000217 alkyl group Chemical group 0.000 claims description 22
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 22
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
• 201000011510 cancer Diseases 0.000 claims description 21
• 125000003545 alkoxy group Chemical group 0.000 claims description 20
• 150000001251 acridines Chemical class 0.000 claims description 16
• CCVDVQHIQPCZBN-UHFFFAOYSA-N 5-methoxy-9-oxo-10h-acridine-4-carboxamide Chemical compound N1C2=C(C(N)=O)C=CC=C2C(=O)C2=C1C(OC)=CC=C2 CCVDVQHIQPCZBN-UHFFFAOYSA-N 0.000 claims description 15
• 239000004480 active ingredient Substances 0.000 claims description 15
• 125000005843 halogen group Chemical group 0.000 claims description 15
• 239000002253 acid Substances 0.000 claims description 12
• 125000004414 alkyl thio group Chemical group 0.000 claims description 12
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 12
• 229910052717 sulfur Inorganic materials 0.000 claims description 11
• 241000124008 Mammalia Species 0.000 claims description 9
• 230000035945 sensitivity Effects 0.000 claims description 9
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 7
• 125000004434 sulfur atom Chemical group 0.000 claims description 7
• 125000001544 thienyl group Chemical group 0.000 claims description 6
• 239000013543 active substance Substances 0.000 claims description 5
• IAKHMKGGTNLKSZ-INIZCTEOSA-N (S)-colchicine Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(OC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC IAKHMKGGTNLKSZ-INIZCTEOSA-N 0.000 claims description 4
• CYMHUYGZYLXSOE-UHFFFAOYSA-N 5-fluoro-9-oxo-10h-acridine-4-carboxamide Chemical compound N1C2=C(F)C=CC=C2C(=O)C2=C1C(C(=O)N)=CC=C2 CYMHUYGZYLXSOE-UHFFFAOYSA-N 0.000 claims description 4
• XRBCKNGUORSKEL-UHFFFAOYSA-N 5-methyl-9-oxo-10h-acridine-4-carboxamide Chemical compound N1C2=C(C(N)=O)C=CC=C2C(=O)C2=C1C(C)=CC=C2 XRBCKNGUORSKEL-UHFFFAOYSA-N 0.000 claims description 4
• KCBDLLNCTLQLPL-UHFFFAOYSA-N acridine-4-carboxamide Chemical compound C1=CC=C2N=C3C(C(=O)N)=CC=CC3=CC2=C1 KCBDLLNCTLQLPL-UHFFFAOYSA-N 0.000 claims description 4
• 229910052731 fluorine Inorganic materials 0.000 claims description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 4
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 3
• 125000001153 fluoro group Chemical group F* 0.000 claims description 3
• 238000004519 manufacturing process Methods 0.000 claims description 3
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
• ZBOHWRYXWSILRQ-UHFFFAOYSA-N 5-methylsulfanyl-9-oxo-10H-acridine-4-carboxamide Chemical compound CSC1=C2NC3=C(C=CC=C3C(=O)C2=CC=C1)C(N)=O ZBOHWRYXWSILRQ-UHFFFAOYSA-N 0.000 claims description 2
• 108010092160 Dactinomycin Proteins 0.000 claims description 2
• 229930012538 Paclitaxel Natural products 0.000 claims description 2
• 229930183665 actinomycin Natural products 0.000 claims description 2
• 229930013930 alkaloid Natural products 0.000 claims description 2
• 125000003277 amino group Chemical group 0.000 claims description 2
• XCPGHVQEEXUHNC-UHFFFAOYSA-N amsacrine Chemical compound COC1=CC(NS(C)(=O)=O)=CC=C1NC1=C(C=CC=C2)C2=NC2=CC=CC=C12 XCPGHVQEEXUHNC-UHFFFAOYSA-N 0.000 claims description 2
• 229960001220 amsacrine Drugs 0.000 claims description 2
• 239000011230 binding agent Substances 0.000 claims description 2
• 150000003857 carboxamides Chemical group 0.000 claims description 2
• 229960001338 colchicine Drugs 0.000 claims description 2
• 239000002552 dosage form Substances 0.000 claims description 2
• KKZJGLLVHKMTCM-UHFFFAOYSA-N mitoxantrone Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO KKZJGLLVHKMTCM-UHFFFAOYSA-N 0.000 claims description 2
• 229960001156 mitoxantrone Drugs 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
• 229910052736 halogen Inorganic materials 0.000 claims 3
• 150000002367 halogens Chemical class 0.000 claims 3
• DZBUGLKDJFMEHC-UHFFFAOYSA-N benzoquinolinylidene Natural products C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims 2
• KHMNIDSQPUUKIE-UHFFFAOYSA-N CCN(C1=NC=CC2=CC=CC=C21)C(=O)C3=CC=C(C4=CC5=CC=CC=C5N=C34)C6=CC=CC=C6 Chemical compound CCN(C1=NC=CC2=CC=CC=C21)C(=O)C3=CC=C(C4=CC5=CC=CC=C5N=C34)C6=CC=CC=C6 KHMNIDSQPUUKIE-UHFFFAOYSA-N 0.000 claims 1
• 241001465754 Metazoa Species 0.000 claims 1
• 229940045799 anthracyclines and related substance Drugs 0.000 claims 1
• 239000007822 coupling agent Substances 0.000 claims 1
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
• 239000011593 sulfur Substances 0.000 claims 1
• 229940127089 cytotoxic agent Drugs 0.000 abstract description 2
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
• 229940041181 antineoplastic drug Drugs 0.000 abstract 1
• 208000016691 refractory malignant neoplasm Diseases 0.000 abstract 1
• 239000000543 intermediate Substances 0.000 description 423
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 317
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 266
• 239000000047 product Substances 0.000 description 216
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 201
• 239000000243 solution Substances 0.000 description 182
• 239000003921 oil Substances 0.000 description 155
• 235000019198 oils Nutrition 0.000 description 155
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 141
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 132
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 129
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 123
• 238000004458 analytical method Methods 0.000 description 119
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 93
• 235000019441 ethanol Nutrition 0.000 description 92
• 238000005481 NMR spectroscopy Methods 0.000 description 91
• 238000002425 crystallisation Methods 0.000 description 88
• 230000008025 crystallization Effects 0.000 description 88
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 84
• 239000007787 solid Substances 0.000 description 73
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
• 239000000706 filtrate Substances 0.000 description 61
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 57
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 56
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 45
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 45
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 42
• ZDSRKZQRHDTJCK-UHFFFAOYSA-N 5-methoxy-9-oxo-10h-acridine-4-carboxylic acid Chemical compound N1C2=C(C(O)=O)C=CC=C2C(=O)C2=C1C(OC)=CC=C2 ZDSRKZQRHDTJCK-UHFFFAOYSA-N 0.000 description 40
• 238000004440 column chromatography Methods 0.000 description 39
• 239000000284 extract Substances 0.000 description 35
• 238000010992 reflux Methods 0.000 description 35
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 33
• 239000003054 catalyst Substances 0.000 description 32
• BATAOFZEDHPRTM-UHFFFAOYSA-N 9-oxo-10h-acridine-4-carboxylic acid Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C(C(=O)O)=CC=C2 BATAOFZEDHPRTM-UHFFFAOYSA-N 0.000 description 31
• 230000008878 coupling Effects 0.000 description 28
• 238000010168 coupling process Methods 0.000 description 28
• 238000005859 coupling reaction Methods 0.000 description 28
• 229910000027 potassium carbonate Inorganic materials 0.000 description 28
• 235000011181 potassium carbonates Nutrition 0.000 description 28
• 239000012044 organic layer Substances 0.000 description 26
• NWUASPKZTXJPOV-UHFFFAOYSA-N 5-fluoro-9-oxo-10h-acridine-4-carboxylic acid Chemical compound N1C2=C(F)C=CC=C2C(=O)C2=C1C(C(=O)O)=CC=C2 NWUASPKZTXJPOV-UHFFFAOYSA-N 0.000 description 24
• CEIXWJHURKEBMQ-UHFFFAOYSA-N Heliamine Chemical compound C1CNCC2=C1C=C(OC)C(OC)=C2 CEIXWJHURKEBMQ-UHFFFAOYSA-N 0.000 description 24
• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 23
• ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 22
• 238000001953 recrystallisation Methods 0.000 description 22
• 239000000725 suspension Substances 0.000 description 22
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
• 238000003756 stirring Methods 0.000 description 20
• 210000004881 tumor cell Anatomy 0.000 description 19
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 17
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 16
• 210000004027 cell Anatomy 0.000 description 16
• 239000003480 eluent Substances 0.000 description 16
• 239000012280 lithium aluminium hydride Substances 0.000 description 16
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
• 239000002904 solvent Substances 0.000 description 15
• ZBJTUFBBPAZNCZ-UHFFFAOYSA-N 5-methyl-9-oxo-10h-acridine-4-carboxylic acid Chemical compound N1C2=C(C(O)=O)C=CC=C2C(=O)C2=C1C(C)=CC=C2 ZBJTUFBBPAZNCZ-UHFFFAOYSA-N 0.000 description 14
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
• 238000001816 cooling Methods 0.000 description 12
• 238000002329 infrared spectrum Methods 0.000 description 11
• 238000002844 melting Methods 0.000 description 11
• 230000008018 melting Effects 0.000 description 11
• 239000012074 organic phase Substances 0.000 description 11
• 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 10
• 238000006243 chemical reaction Methods 0.000 description 10
• 239000013078 crystal Substances 0.000 description 10
• AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 10
• 230000009467 reduction Effects 0.000 description 10
• 238000010898 silica gel chromatography Methods 0.000 description 10
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
• AVDLFIONKHGQAP-UHFFFAOYSA-N 4-nitrophenoxyacetic acid Chemical compound OC(=O)COC1=CC=C([N+]([O-])=O)C=C1 AVDLFIONKHGQAP-UHFFFAOYSA-N 0.000 description 9
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
• 238000010521 absorption reaction Methods 0.000 description 9
• 238000001914 filtration Methods 0.000 description 9
• 239000011541 reaction mixture Substances 0.000 description 9
• GDALETGZDYOOGB-UHFFFAOYSA-N Acridone Natural products C1=C(O)C=C2N(C)C3=CC=CC=C3C(=O)C2=C1O GDALETGZDYOOGB-UHFFFAOYSA-N 0.000 description 8
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
• FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical group C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 description 8
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
• 238000001665 trituration Methods 0.000 description 8
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
• 230000000259 anti-tumor effect Effects 0.000 description 7
• 229910052938 sodium sulfate Inorganic materials 0.000 description 7
• 235000011152 sodium sulphate Nutrition 0.000 description 7
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 7
• WUTIWOZYHHSBBU-UHFFFAOYSA-N 3-methoxy-4-nitrobenzaldehyde Chemical compound COC1=CC(C=O)=CC=C1[N+]([O-])=O WUTIWOZYHHSBBU-UHFFFAOYSA-N 0.000 description 6
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
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• HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
• 239000003112 inhibitor Substances 0.000 description 6
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 6
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
• 235000017557 sodium bicarbonate Nutrition 0.000 description 6
• LIBYGKUWXRBMPA-UHFFFAOYSA-N 1-(3-bromopropoxy)-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(OCCCBr)C=C1 LIBYGKUWXRBMPA-UHFFFAOYSA-N 0.000 description 5
• WQMLUHZFRFCQDB-UHFFFAOYSA-N 4-(4-nitrophenyl)butyric acid Chemical compound OC(=O)CCCC1=CC=C([N+]([O-])=O)C=C1 WQMLUHZFRFCQDB-UHFFFAOYSA-N 0.000 description 5
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
• 125000003118 aryl group Chemical group 0.000 description 5
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 5
• 229960004679 doxorubicin Drugs 0.000 description 5
• 230000007062 hydrolysis Effects 0.000 description 5
• 238000006460 hydrolysis reaction Methods 0.000 description 5
• 239000002244 precipitate Substances 0.000 description 5
• VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 description 4
• VZOPVJNBOQOLPN-UHFFFAOYSA-N 3-(p-nitrophenyl)propanoic acid Chemical compound OC(=O)CCC1=CC=C([N+]([O-])=O)C=C1 VZOPVJNBOQOLPN-UHFFFAOYSA-N 0.000 description 4
• LTPVSOCPYWDIFU-UHFFFAOYSA-N 4-methoxyphenylethylamine Chemical compound COC1=CC=C(CCN)C=C1 LTPVSOCPYWDIFU-UHFFFAOYSA-N 0.000 description 4
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
• 241000282412 Homo Species 0.000 description 4
• BZORFPDSXLZWJF-UHFFFAOYSA-N N,N-dimethyl-1,4-phenylenediamine Chemical compound CN(C)C1=CC=C(N)C=C1 BZORFPDSXLZWJF-UHFFFAOYSA-N 0.000 description 4
• 229910000288 alkali metal carbonate Inorganic materials 0.000 description 4
• 150000008041 alkali metal carbonates Chemical class 0.000 description 4
• 239000003638 chemical reducing agent Substances 0.000 description 4
• 125000001309 chloro group Chemical group Cl* 0.000 description 4
• 238000010790 dilution Methods 0.000 description 4
• 239000012895 dilution Substances 0.000 description 4
• 239000012259 ether extract Substances 0.000 description 4
• 239000010410 layer Substances 0.000 description 4
• NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 4
• 239000012265 solid product Substances 0.000 description 4
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