IL101139A - Imidazoacridines and their use against large malignancies - Google Patents
Imidazoacridines and their use against large malignanciesInfo
- Publication number
- IL101139A IL101139A IL10113992A IL10113992A IL101139A IL 101139 A IL101139 A IL 101139A IL 10113992 A IL10113992 A IL 10113992A IL 10113992 A IL10113992 A IL 10113992A IL 101139 A IL101139 A IL 101139A
- Authority
- IL
- Israel
- Prior art keywords
- alkyl
- compound
- compounds
- formula
- hydrogen
- Prior art date
Links
- 230000000118 anti-neoplastic effect Effects 0.000 title abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 70
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- 239000002253 acid Substances 0.000 claims abstract description 13
- 239000012458 free base Substances 0.000 claims abstract description 10
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
- 150000002431 hydrogen Chemical group 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims description 41
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 5
- 235000019253 formic acid Nutrition 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 208000026310 Breast neoplasm Diseases 0.000 claims description 2
- 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 claims description 2
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 208000029742 colonic neoplasm Diseases 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 abstract description 11
- 238000011282 treatment Methods 0.000 abstract description 8
- 238000011321 prophylaxis Methods 0.000 abstract description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 239000000047 product Substances 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- 210000004027 cell Anatomy 0.000 description 6
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 6
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 238000001727 in vivo Methods 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- 206010028980 Neoplasm Diseases 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 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
- 229960004679 doxorubicin Drugs 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
- 239000004615 ingredient Substances 0.000 description 3
- -1 nitro, chloro, methyl Chemical group 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VQHITFFJBFOMBG-UHFFFAOYSA-N 6-(4-methylpiperazin-1-yl)-11h-benzo[b][1,4]benzodiazepine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=CC=CC=C12 VQHITFFJBFOMBG-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241001529936 Murinae Species 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 241000699670 Mus sp. Species 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
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000004103 aminoalkyl group Chemical group 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 239000003054 catalyst Substances 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
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 210000001853 liver microsome Anatomy 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
- DMEKUKDWAIXWSL-UHFFFAOYSA-N n,n-dimethyl-7-nitro-9h-fluoren-2-amine Chemical compound [O-][N+](=O)C1=CC=C2C3=CC=C(N(C)C)C=C3CC2=C1 DMEKUKDWAIXWSL-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
- 150000003254 radicals Chemical class 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material 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
- 239000003826 tablet Substances 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
- VLXSIHLNPYRFFN-UHFFFAOYSA-N 1,4-dioxane;methanol Chemical compound OC.C1COCCO1 VLXSIHLNPYRFFN-UHFFFAOYSA-N 0.000 description 1
- HGCUZKFNPOOGSK-UHFFFAOYSA-N 1-[2-(diethylamino)ethylamino]-7-methoxy-4-nitro-10h-acridin-9-one Chemical compound N1C2=CC=C(OC)C=C2C(=O)C2=C1C([N+]([O-])=O)=CC=C2NCCN(CC)CC HGCUZKFNPOOGSK-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- JWZUXKYELFWKNJ-UHFFFAOYSA-N 4h-acridin-3-one Chemical compound C1=CC=C2C=C(C=CC(=O)C3)C3=NC2=C1 JWZUXKYELFWKNJ-UHFFFAOYSA-N 0.000 description 1
- MUHZKZDGCPQBMI-UHFFFAOYSA-N 5-amino-2-methoxy-10h-acridin-9-one Chemical class C1=CC=C2C(=O)C3=CC(OC)=CC=C3NC2=C1N MUHZKZDGCPQBMI-UHFFFAOYSA-N 0.000 description 1
- JCBYXNSOLUVGTF-UHFFFAOYSA-N 6-piperazin-1-yl-11h-benzo[b][1,4]benzodiazepine Chemical compound C1CNCCN1C1=NC2=CC=CC=C2NC2=CC=CC=C12 JCBYXNSOLUVGTF-UHFFFAOYSA-N 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- 238000004435 EPR spectroscopy Methods 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
- 101150085390 RPM1 gene Proteins 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
- 101150092978 Slc25a4 gene Proteins 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
- 125000003277 amino group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000000719 anti-leukaemic effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000003556 assay Methods 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
- 239000000872 buffer Substances 0.000 description 1
- 201000011510 cancer Diseases 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
- 239000000969 carrier Substances 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 238000002512 chemotherapy 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
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001362 electron spin resonance spectrum Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 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
- 235000013355 food flavoring agent Nutrition 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
- QYRFJLLXPINATB-UHFFFAOYSA-N hydron;2,4,5,6-tetrafluorobenzene-1,3-diamine;dichloride Chemical class Cl.Cl.NC1=C(F)C(N)=C(F)C(F)=C1F QYRFJLLXPINATB-UHFFFAOYSA-N 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
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 201000010982 kidney cancer Diseases 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 208000003747 lymphoid leukemia Diseases 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 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
- 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
- 239000002798 polar solvent Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 235000019624 protein content Nutrition 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 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
- 125000001424 substituent group Chemical group 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
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical group 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 230000008467 tissue growth Effects 0.000 description 1
- 230000000699 topical effect Effects 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)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB919104548A GB9104548D0 (en) | 1991-03-05 | 1991-03-05 | Antineoplastic modified imidazoacridines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL101139A0 IL101139A0 (en) | 1992-11-15 |
| IL101139A true IL101139A (en) | 1995-01-24 |
Family
ID=10690967
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL10113992A IL101139A (en) | 1991-03-05 | 1992-03-04 | Imidazoacridines and their use against large malignancies |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US5231100A (pl) |
| EP (2) | EP0502668A1 (pl) |
| JP (1) | JP3176062B2 (pl) |
| AT (1) | ATE153664T1 (pl) |
| AU (1) | AU654700B2 (pl) |
| CA (1) | CA2051356C (pl) |
| DE (1) | DE69220048T2 (pl) |
| DK (1) | DK0579614T3 (pl) |
| ES (1) | ES2103931T3 (pl) |
| GB (2) | GB9104548D0 (pl) |
| GR (1) | GR3024485T3 (pl) |
| IE (1) | IE66260B1 (pl) |
| IL (1) | IL101139A (pl) |
| NO (1) | NO300175B1 (pl) |
| PL (1) | PL167640B1 (pl) |
| WO (1) | WO1992015583A1 (pl) |
| ZA (1) | ZA921615B (pl) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0604181A1 (en) * | 1992-12-21 | 1994-06-29 | Eli Lilly And Company | Antitumor compositions and method of treatment |
| 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 |
| AU7456396A (en) * | 1995-11-02 | 1997-05-22 | Warner-Lambert Company | Inhibition of amyloidosis by 9-acridinones |
| ATE211471T1 (de) | 1996-04-12 | 2002-01-15 | Us Gov Health & Human Serv | Acridonderivate als antineoplastische-und antiretrovirale mittel |
| 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 |
| AU2001240054B2 (en) * | 2000-03-07 | 2005-08-11 | The Government Of The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | 1,8-Naphthalimide Imidazo[4,5,1-de]acridones with Anti-Tumor Activity |
| JP2008528616A (ja) * | 2005-01-28 | 2008-07-31 | ザンサス ファーマシューティカルズ， インコーポレイテッド | 炎症性疾患および脱髄性疾患を処置するための化合物 |
| WO2007092436A2 (en) * | 2006-02-08 | 2007-08-16 | Xanthus Pharmaceuticals, Inc. | Compounds for treating inflammatory disorders, demyelinating disorders and cancers |
| WO2007143096A2 (en) * | 2006-06-02 | 2007-12-13 | Xanthus Pharmaceuticals, Inc. | Compounds for treating cancers |
| US20100016300A1 (en) * | 2006-08-02 | 2010-01-21 | Ajami Alfred M | Imidazoacridine Compounds for Treating FLT3-Mediated Disorders |
| WO2008016700A2 (en) * | 2006-08-02 | 2008-02-07 | Xanthus Pharmaceuticals, Inc. | N-oxide compounds for therapeutics uses |
| WO2008016660A2 (en) * | 2006-08-02 | 2008-02-07 | Xanthus Pharmaceuticals, Inc. | Imidazoacridine compounds for treating leukemias |
| 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 (en) * | 2015-03-20 | 2017-10-04 | Politechnika Gdanska | Asymmetric bis-acridines with antitumor activity and use thereof |
| CN108135863B (zh) * | 2015-04-27 | 2021-07-27 | 特拉维夫医疗中心医学研究基础设施和保健服务基金会 | 用于治疗炎性和过度增殖性病况的egr1靶向分子 |
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| 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 US US07/760,694 patent/US5231100A/en not_active Expired - Lifetime
- 1991-09-16 CA CA002051356A patent/CA2051356C/en not_active Expired - Fee Related
-
1992
- 1992-02-28 WO PCT/GB1992/000360 patent/WO1992015583A1/en not_active Ceased
- 1992-02-28 EP EP92301732A patent/EP0502668A1/en active Pending
- 1992-02-28 GB GB9204315A patent/GB2253396B/en not_active Expired - Fee Related
- 1992-02-28 ES ES92905201T patent/ES2103931T3/es not_active Expired - Lifetime
- 1992-02-28 EP EP92905201A patent/EP0579614B1/en not_active Expired - Lifetime
- 1992-02-28 AU AU12743/92A patent/AU654700B2/en not_active Ceased
- 1992-02-28 JP JP50506892A patent/JP3176062B2/ja not_active Expired - Fee Related
- 1992-02-28 DK DK92905201.7T patent/DK0579614T3/da active
- 1992-02-28 AT AT92905201T patent/ATE153664T1/de not_active IP Right Cessation
- 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
- 1992-03-03 IE IE920677A patent/IE66260B1/en not_active IP Right Cessation
- 1992-03-04 IL IL10113992A patent/IL101139A/en not_active IP Right Cessation
- 1992-03-04 ZA ZA921615A patent/ZA921615B/xx unknown
-
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 |
|---|---|
| NO933147D0 (no) | 1993-09-03 |
| GB2253396B (en) | 1994-08-10 |
| AU1274392A (en) | 1992-10-06 |
| NO300175B1 (no) | 1997-04-21 |
| CA2051356A1 (en) | 1992-09-06 |
| GB9204315D0 (en) | 1992-04-08 |
| AU654700B2 (en) | 1994-11-17 |
| JP3176062B2 (ja) | 2001-06-11 |
| DE69220048T2 (de) | 1997-10-02 |
| DK0579614T3 (da) | 1997-12-15 |
| PL167640B1 (pl) | 1995-10-31 |
| WO1992015583A1 (en) | 1992-09-17 |
| JPH06508102A (ja) | 1994-09-14 |
| GR3024485T3 (en) | 1997-11-28 |
| IL101139A0 (en) | 1992-11-15 |
| DE69220048D1 (de) | 1997-07-03 |
| EP0579614A1 (en) | 1994-01-26 |
| EP0579614B1 (en) | 1997-05-28 |
| IE920677A1 (en) | 1992-09-09 |
| CA2051356C (en) | 2002-01-08 |
| NO933147L (no) | 1993-09-03 |
| ATE153664T1 (de) | 1997-06-15 |
| US5231100A (en) | 1993-07-27 |
| GB9104548D0 (en) | 1991-04-17 |
| GB2253396A (en) | 1992-09-09 |
| IE66260B1 (en) | 1995-12-27 |
| ZA921615B (en) | 1992-11-25 |
| ES2103931T3 (es) | 1997-10-01 |
| EP0502668A1 (en) | 1992-09-09 |
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