NO300175B1 - Imidazoakridiner og deres antineoplastiske sammensetninger - Google Patents
Imidazoakridiner og deres antineoplastiske sammensetninger Download PDFInfo
- Publication number
- NO300175B1 NO300175B1 NO933147A NO933147A NO300175B1 NO 300175 B1 NO300175 B1 NO 300175B1 NO 933147 A NO933147 A NO 933147A NO 933147 A NO933147 A NO 933147A NO 300175 B1 NO300175 B1 NO 300175B1
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- Norway
- Prior art keywords
- compounds
- alkyl
- compound
- formula
- procedure
- Prior art date
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- 230000000118 anti-neoplastic effect Effects 0.000 title abstract description 8
- 239000000203 mixture Substances 0.000 title description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 64
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 239000002253 acid Substances 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 239000012458 free base Substances 0.000 abstract description 14
- 208000032839 leukemia Diseases 0.000 abstract description 7
- 238000011282 treatment Methods 0.000 abstract description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- 238000011321 prophylaxis Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 description 38
- 239000000047 product Substances 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 8
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 8
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 239000002585 base Substances 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000013067 intermediate product Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 4
- 206010028980 Neoplasm Diseases 0.000 description 4
- 230000000719 anti-leukaemic effect Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 235000019253 formic acid Nutrition 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 241001529936 Murinae Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000004103 aminoalkyl group Chemical group 0.000 description 3
- 229940034982 antineoplastic agent Drugs 0.000 description 3
- 239000002246 antineoplastic agent Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 201000011510 cancer Diseases 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229960004679 doxorubicin Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
- 150000003840 hydrochlorides Chemical class 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
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- 230000002265 prevention Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 101150085390 RPM1 gene Proteins 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000001472 cytotoxic effect Effects 0.000 description 2
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 210000001853 liver microsome Anatomy 0.000 description 2
- 208000003747 lymphoid leukemia Diseases 0.000 description 2
- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 2
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
- VLXSIHLNPYRFFN-UHFFFAOYSA-N 1,4-dioxane;methanol Chemical compound OC.C1COCCO1 VLXSIHLNPYRFFN-UHFFFAOYSA-N 0.000 description 1
- WUQQKUISNKRKFK-UHFFFAOYSA-N 1-chloro-7-methoxy-4-nitro-10h-acridin-9-one Chemical compound C1=CC(Cl)=C2C(=O)C3=CC(OC)=CC=C3NC2=C1[N+]([O-])=O WUQQKUISNKRKFK-UHFFFAOYSA-N 0.000 description 1
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical group C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- 238000004435 EPR spectroscopy Methods 0.000 description 1
- 239000001692 EU approved anti-caking agent Substances 0.000 description 1
- 208000001382 Experimental Melanoma Diseases 0.000 description 1
- 101001108356 Homo sapiens Nardilysin Proteins 0.000 description 1
- 206010022998 Irritability Diseases 0.000 description 1
- 208000008839 Kidney Neoplasms Diseases 0.000 description 1
- 208000028018 Lymphocytic leukaemia Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 102100021850 Nardilysin Human genes 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 206010038389 Renal cancer Diseases 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 208000009956 adenocarcinoma Diseases 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 201000008275 breast carcinoma Diseases 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- -1 cachets Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 231100000457 cardiotoxic Toxicity 0.000 description 1
- 230000001451 cardiotoxic effect Effects 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 238000001362 electron spin resonance spectrum Methods 0.000 description 1
- 239000012894 fetal calf serum Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 229950006191 gluconic acid Drugs 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 230000033444 hydroxylation Effects 0.000 description 1
- 238000005805 hydroxylation reaction Methods 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 201000010982 kidney cancer Diseases 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229960000448 lactic acid Drugs 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229940098895 maleic acid Drugs 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 150000005217 methyl ethers Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000001613 neoplastic effect Effects 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- HVZWVEKIQMJYIK-UHFFFAOYSA-N nitryl chloride Chemical compound [O-][N+](Cl)=O HVZWVEKIQMJYIK-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 238000005556 structure-activity relationship Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB919104548A GB9104548D0 (en) | 1991-03-05 | 1991-03-05 | Antineoplastic modified imidazoacridines |
| PCT/GB1992/000360 WO1992015583A1 (fr) | 1991-03-05 | 1992-02-28 | Imidazoacridines et leur utilisation en tant qu'antineoplasique |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO933147L NO933147L (no) | 1993-09-03 |
| NO933147D0 NO933147D0 (no) | 1993-09-03 |
| NO300175B1 true NO300175B1 (no) | 1997-04-21 |
Family
ID=10690967
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO933147A NO300175B1 (no) | 1991-03-05 | 1993-09-03 | Imidazoakridiner og deres antineoplastiske sammensetninger |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US5231100A (fr) |
| EP (2) | EP0579614B1 (fr) |
| JP (1) | JP3176062B2 (fr) |
| AT (1) | ATE153664T1 (fr) |
| AU (1) | AU654700B2 (fr) |
| CA (1) | CA2051356C (fr) |
| DE (1) | DE69220048T2 (fr) |
| DK (1) | DK0579614T3 (fr) |
| ES (1) | ES2103931T3 (fr) |
| GB (2) | GB9104548D0 (fr) |
| GR (1) | GR3024485T3 (fr) |
| IE (1) | IE66260B1 (fr) |
| IL (1) | IL101139A (fr) |
| NO (1) | NO300175B1 (fr) |
| PL (1) | PL167640B1 (fr) |
| WO (1) | WO1992015583A1 (fr) |
| ZA (1) | ZA921615B (fr) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0604181A1 (fr) * | 1992-12-21 | 1994-06-29 | Eli Lilly And Company | Compositions antitumeurs et méthodes de traitement |
| US5508289A (en) * | 1994-03-14 | 1996-04-16 | The United States America As Represented By The Department Of Health And Human Services | Bis-acridone chemotherapeutic derivatives |
| US5972956A (en) * | 1995-11-02 | 1999-10-26 | Warner-Lambert Company | Inhibition of amyloidosis by 9-acridinones |
| JP4121151B2 (ja) * | 1996-04-12 | 2008-07-23 | アメリカ合衆国 | 抗新生物薬および抗レトロウイルス薬として有用なアクリドンから誘導された化合物 |
| GB2317888A (en) * | 1996-10-07 | 1998-04-08 | Marek Tadeusz Konieczny | Acridone derivatives and preparation of 8-hydroxy-imidazoacridinone derivatives |
| IT1293525B1 (it) * | 1997-08-01 | 1999-03-01 | Uni Degli Studi Camerino | Bis-acridincarbossiammidi aventi attivita' antitumorale |
| US6664263B2 (en) | 2000-03-07 | 2003-12-16 | The United States Of America As Represented By The Department Of Health And Human Services | 1,8-naphthalimide imidazo{4,5,1-de}acridones with anti-tumor activity |
| CA2596144A1 (fr) * | 2005-01-28 | 2006-08-03 | Xanthus Pharmaceuticals, Inc. | Composes utiles dans le traitement des maladies auto-immunes et des troubles de demyelinisation |
| WO2007092436A2 (fr) * | 2006-02-08 | 2007-08-16 | Xanthus Pharmaceuticals, Inc. | Composes pour le traitement de troubles inflammatoires, de troubles de demyelinisation et de cancers |
| WO2007143096A2 (fr) * | 2006-06-02 | 2007-12-13 | Xanthus Pharmaceuticals, Inc. | Composés destinés au traitement du cancer |
| WO2008016660A2 (fr) * | 2006-08-02 | 2008-02-07 | Xanthus Pharmaceuticals, Inc. | Composés de traitement de la leucémie |
| WO2008016700A2 (fr) * | 2006-08-02 | 2008-02-07 | Xanthus Pharmaceuticals, Inc. | Composés de n-oxyde et utilisations thérapeutiques |
| WO2008016665A2 (fr) * | 2006-08-02 | 2008-02-07 | Xanthus Pharmaceuticals, Inc. | Composés et méthodes de traitement de troubles médiés par flt3 |
| US20080118576A1 (en) * | 2006-08-28 | 2008-05-22 | Dan Theodorescu | Prediction of an agent's or agents' activity across different cells and tissue types |
| US8470844B2 (en) * | 2008-09-11 | 2013-06-25 | Technion Research & Development Foundation Limited | Imidazoacridinone derivative compounds and methods for their use |
| EP3070078B1 (fr) * | 2015-03-20 | 2017-10-04 | Politechnika Gdanska | Bisacridines asymmetriques at leur utilisation en tant qu`agents anti-tumorales |
| ES2951653T3 (es) * | 2015-04-27 | 2023-10-24 | Medical Res Infrastructure & Health Services Fund Tel Aviv Medical Ct | Moléculas dirigidas a EGR1 para el tratamiento de afecciones inflamatorias e hiperproliferativas |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1037377A (en) * | 1964-09-02 | 1966-07-27 | Mitsubishi Chem Ind | Naphthoylene-arylimidazole disperse dyestuffs |
| US4626540A (en) * | 1983-11-08 | 1986-12-02 | Warner-Lambert Company | Substituted 1-amino-4-nitro-acridinones and methods of treating bacterial infections and leukemia with them |
| JP2795460B2 (ja) * | 1988-06-20 | 1998-09-10 | 協和醗酵工業株式会社 | ピラゾロアクリドン誘導体 |
-
1991
- 1991-03-05 GB GB919104548A patent/GB9104548D0/en active Pending
- 1991-09-16 CA CA002051356A patent/CA2051356C/fr not_active Expired - Fee Related
- 1991-09-16 US US07/760,694 patent/US5231100A/en not_active Expired - Lifetime
-
1992
- 1992-02-28 EP EP92905201A patent/EP0579614B1/fr not_active Expired - Lifetime
- 1992-02-28 WO PCT/GB1992/000360 patent/WO1992015583A1/fr active IP Right Grant
- 1992-02-28 GB GB9204315A patent/GB2253396B/en not_active Expired - Fee Related
- 1992-02-28 EP EP92301732A patent/EP0502668A1/fr active Pending
- 1992-02-28 PL PL92300593A patent/PL167640B1/pl not_active IP Right Cessation
- 1992-02-28 DE DE69220048T patent/DE69220048T2/de not_active Expired - Fee Related
- 1992-02-28 AU AU12743/92A patent/AU654700B2/en not_active Ceased
- 1992-02-28 DK DK92905201.7T patent/DK0579614T3/da active
- 1992-02-28 JP JP50506892A patent/JP3176062B2/ja not_active Expired - Fee Related
- 1992-02-28 ES ES92905201T patent/ES2103931T3/es not_active Expired - Lifetime
- 1992-02-28 AT AT92905201T patent/ATE153664T1/de not_active IP Right Cessation
- 1992-03-03 IE IE920677A patent/IE66260B1/en not_active IP Right Cessation
- 1992-03-04 ZA ZA921615A patent/ZA921615B/xx unknown
- 1992-03-04 IL IL10113992A patent/IL101139A/en not_active IP Right Cessation
-
1993
- 1993-09-03 NO NO933147A patent/NO300175B1/no unknown
-
1997
- 1997-08-19 GR GR970402124T patent/GR3024485T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2051356A1 (fr) | 1992-09-06 |
| PL167640B1 (pl) | 1995-10-31 |
| GR3024485T3 (en) | 1997-11-28 |
| ES2103931T3 (es) | 1997-10-01 |
| IE920677A1 (en) | 1992-09-09 |
| EP0579614A1 (fr) | 1994-01-26 |
| GB2253396B (en) | 1994-08-10 |
| DE69220048T2 (de) | 1997-10-02 |
| IL101139A0 (en) | 1992-11-15 |
| IE66260B1 (en) | 1995-12-27 |
| IL101139A (en) | 1995-01-24 |
| DE69220048D1 (de) | 1997-07-03 |
| ATE153664T1 (de) | 1997-06-15 |
| NO933147L (no) | 1993-09-03 |
| WO1992015583A1 (fr) | 1992-09-17 |
| GB9104548D0 (en) | 1991-04-17 |
| US5231100A (en) | 1993-07-27 |
| GB2253396A (en) | 1992-09-09 |
| JPH06508102A (ja) | 1994-09-14 |
| AU1274392A (en) | 1992-10-06 |
| AU654700B2 (en) | 1994-11-17 |
| EP0502668A1 (fr) | 1992-09-09 |
| GB9204315D0 (en) | 1992-04-08 |
| ZA921615B (en) | 1992-11-25 |
| CA2051356C (fr) | 2002-01-08 |
| DK0579614T3 (da) | 1997-12-15 |
| JP3176062B2 (ja) | 2001-06-11 |
| NO933147D0 (no) | 1993-09-03 |
| EP0579614B1 (fr) | 1997-05-28 |
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