FI71726C - Foerfarande foer framstaellning av terapeutiskt anvaendbara antracen-9,10-bis-karbonylderivat. - Google Patents
Foerfarande foer framstaellning av terapeutiskt anvaendbara antracen-9,10-bis-karbonylderivat. Download PDFInfo
- Publication number
- FI71726C FI71726C FI783621A FI783621A FI71726C FI 71726 C FI71726 C FI 71726C FI 783621 A FI783621 A FI 783621A FI 783621 A FI783621 A FI 783621A FI 71726 C FI71726 C FI 71726C
- Authority
- FI
- Finland
- Prior art keywords
- anthracenedicarboxaldehyde
- bis
- dihydro
- anthracene
- hours
- Prior art date
Links
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 59
- 239000000203 mixture Substances 0.000 claims description 59
- 150000001875 compounds Chemical class 0.000 claims description 48
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 22
- -1 anthracene-9,10-bis-carbonyl Chemical class 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 17
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 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 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- 239000000174 gluconic acid Substances 0.000 claims description 2
- 235000012208 gluconic acid Nutrition 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- 239000011976 maleic acid Substances 0.000 claims description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 2
- WPDAVTSOEQEGMS-UHFFFAOYSA-N 9,10-dihydroanthracene Chemical group C1=CC=C2CC3=CC=CC=C3CC2=C1 WPDAVTSOEQEGMS-UHFFFAOYSA-N 0.000 claims 1
- 206010008631 Cholera Diseases 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 117
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 40
- 239000000243 solution Substances 0.000 description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
- 239000000047 product Substances 0.000 description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 238000002844 melting Methods 0.000 description 30
- 230000008018 melting Effects 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- 239000013078 crystal Substances 0.000 description 27
- 229960002949 fluorouracil Drugs 0.000 description 25
- 239000007787 solid Substances 0.000 description 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 24
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 24
- 229960000583 acetic acid Drugs 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 238000001914 filtration Methods 0.000 description 17
- 239000000725 suspension Substances 0.000 description 17
- 239000004480 active ingredient Substances 0.000 description 16
- DIESEUQXOPYZEJ-UHFFFAOYSA-N 4,5-dihydro-1h-imidazol-2-ylhydrazine;dihydrochloride Chemical compound Cl.Cl.NNC1=NCCN1 DIESEUQXOPYZEJ-UHFFFAOYSA-N 0.000 description 15
- 150000005676 cyclic carbonates Chemical class 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- VAYTZRYEBVHVLE-UHFFFAOYSA-N 1,3-dioxol-2-one Chemical compound O=C1OC=CO1 VAYTZRYEBVHVLE-UHFFFAOYSA-N 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 10
- 206010028980 Neoplasm Diseases 0.000 description 10
- 239000012362 glacial acetic acid Substances 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 150000004056 anthraquinones Chemical class 0.000 description 9
- 230000004083 survival effect Effects 0.000 description 9
- SBRUFOSORMQHES-UHFFFAOYSA-N anthracene-9,10-dialdehyde Chemical class C1=CC=C2C(C=O)=C(C=CC=C3)C3=C(C=O)C2=C1 SBRUFOSORMQHES-UHFFFAOYSA-N 0.000 description 8
- 150000001454 anthracenes Chemical class 0.000 description 8
- ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- GYMFBYTZOGMSQJ-UHFFFAOYSA-N 2-methylanthracene Chemical compound C1=CC=CC2=CC3=CC(C)=CC=C3C=C21 GYMFBYTZOGMSQJ-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 208000028018 Lymphocytic leukaemia Diseases 0.000 description 6
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 230000000844 anti-bacterial effect Effects 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- 230000002401 inhibitory effect Effects 0.000 description 6
- 208000003747 lymphoid leukemia Diseases 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- IXYCAHBABUNCQU-UHFFFAOYSA-N 2,3-dimethylanthracene-9,10-dicarbaldehyde Chemical compound C1=CC=C2C(C=O)=C(C=C(C(C)=C3)C)C3=C(C=O)C2=C1 IXYCAHBABUNCQU-UHFFFAOYSA-N 0.000 description 5
- OGRVGOVHYDCOCU-UHFFFAOYSA-N 2,6-difluoroanthracene-9,10-dicarbaldehyde Chemical compound C1=C(F)C=CC2=C(C=O)C3=CC(F)=CC=C3C(C=O)=C21 OGRVGOVHYDCOCU-UHFFFAOYSA-N 0.000 description 5
- SDKQPJANFBGTSH-UHFFFAOYSA-N 2,6-dihydroxyanthracene-9,10-dicarbaldehyde Chemical compound C1=C(O)C=CC2=C(C=O)C3=CC(O)=CC=C3C(C=O)=C21 SDKQPJANFBGTSH-UHFFFAOYSA-N 0.000 description 5
- PJOGDERCGRELPY-UHFFFAOYSA-N 2-hydroxyanthracene-9,10-dicarbaldehyde Chemical compound C1=CC=CC2=C(C=O)C3=CC(O)=CC=C3C(C=O)=C21 PJOGDERCGRELPY-UHFFFAOYSA-N 0.000 description 5
- ILPDPMBPORRFKM-UHFFFAOYSA-N 2-methylanthracene-9,10-dicarbaldehyde Chemical compound C1=CC=CC2=C(C=O)C3=CC(C)=CC=C3C(C=O)=C21 ILPDPMBPORRFKM-UHFFFAOYSA-N 0.000 description 5
- 229920001817 Agar Polymers 0.000 description 5
- QXAZWDRIKVHWEM-UHFFFAOYSA-N C1CCNC(NN=CC=2C3=CC=CC=C3C(C=NNC=3NCCCN=3)=C3C=CC=CC3=2)=N1 Chemical compound C1CCNC(NN=CC=2C3=CC=CC=C3C(C=NNC=3NCCCN=3)=C3C=CC=CC3=2)=N1 QXAZWDRIKVHWEM-UHFFFAOYSA-N 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 239000008272 agar Substances 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 230000012010 growth Effects 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- LGMCPBWXMKSJSK-UHFFFAOYSA-N 1,2-dihydroxyanthracene-9,10-dicarbaldehyde Chemical compound C1=CC=CC2=C(C=O)C3=C(O)C(O)=CC=C3C(C=O)=C21 LGMCPBWXMKSJSK-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- OGVRJXPGSVLDRD-UHFFFAOYSA-N 2,3-dimethylanthracene Chemical compound C1=CC=C2C=C(C=C(C(C)=C3)C)C3=CC2=C1 OGVRJXPGSVLDRD-UHFFFAOYSA-N 0.000 description 4
- JMZIRXQPMJIQBR-UHFFFAOYSA-N 2-aminoanthracene-9,10-dicarbaldehyde Chemical compound C1=CC=CC2=C(C=O)C3=CC(N)=CC=C3C(C=O)=C21 JMZIRXQPMJIQBR-UHFFFAOYSA-N 0.000 description 4
- GCDBEYOJCZLKMC-UHFFFAOYSA-N 2-hydroxyanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(O)=CC=C3C(=O)C2=C1 GCDBEYOJCZLKMC-UHFFFAOYSA-N 0.000 description 4
- 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
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- PVCRDGNYGWVRCO-UHFFFAOYSA-N ac1l9jkn Chemical compound C12=CC=CC=C2C2C(O)C(O)C1C1=CC=CC=C12 PVCRDGNYGWVRCO-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 4
- 239000003610 charcoal Substances 0.000 description 4
- 235000019253 formic acid Nutrition 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- 208000032839 leukemia Diseases 0.000 description 4
- 201000001441 melanoma Diseases 0.000 description 4
- 230000000684 melanotic effect Effects 0.000 description 4
- 244000005700 microbiome Species 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- BICFLBCKIIIFBI-UHFFFAOYSA-N 1,4-dimethyl-9,10-dihydroanthracene-9,10-dicarbaldehyde Chemical compound O=CC1C2=CC=CC=C2C(C=O)C2=C1C(C)=CC=C2C BICFLBCKIIIFBI-UHFFFAOYSA-N 0.000 description 3
- YSWWLDRVGLUEJD-UHFFFAOYSA-N 1,4-dimethylanthracene-9,10-dicarbaldehyde Chemical compound C1=CC=C2C(C=O)=C3C(C)=CC=C(C)C3=C(C=O)C2=C1 YSWWLDRVGLUEJD-UHFFFAOYSA-N 0.000 description 3
- CREDAWPCPFIZBW-UHFFFAOYSA-N 2,3-dimethyl-9,10-dihydroanthracene-9,10-dicarbaldehyde Chemical compound O=CC1C2=CC=CC=C2C(C=O)C2=C1C=C(C)C(C)=C2 CREDAWPCPFIZBW-UHFFFAOYSA-N 0.000 description 3
- GFXNKJJWMJSPMB-UHFFFAOYSA-N 2-chloroanthracene-9,10-dicarbaldehyde Chemical compound C1=CC=CC2=C(C=O)C3=CC(Cl)=CC=C3C(C=O)=C21 GFXNKJJWMJSPMB-UHFFFAOYSA-N 0.000 description 3
- RGCKGOZRHPZPFP-UHFFFAOYSA-N Alizarin Natural products C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 241000191967 Staphylococcus aureus Species 0.000 description 3
- ZJZODPNCHRCUHS-UHFFFAOYSA-N anthracene-9,10-dicarbaldehyde;dihydrochloride Chemical compound Cl.Cl.C1=CC=C2C(C=O)=C(C=CC=C3)C3=C(C=O)C2=C1 ZJZODPNCHRCUHS-UHFFFAOYSA-N 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 201000011510 cancer Diseases 0.000 description 3
- OFZCIYFFPZCNJE-UHFFFAOYSA-N carisoprodol Chemical compound NC(=O)OCC(C)(CCC)COC(=O)NC(C)C OFZCIYFFPZCNJE-UHFFFAOYSA-N 0.000 description 3
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 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
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- 238000011081 inoculation Methods 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 231100000252 nontoxic Toxicity 0.000 description 3
- 230000003000 nontoxic effect Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- MYFIEDDVDFQDJT-UHFFFAOYSA-N (6-acetyloxy-9,10-diformylanthracen-2-yl) acetate Chemical compound C1=C(OC(C)=O)C=CC2=C(C=O)C3=CC(OC(=O)C)=CC=C3C(C=O)=C21 MYFIEDDVDFQDJT-UHFFFAOYSA-N 0.000 description 2
- FLNHUGMJJMGODI-UHFFFAOYSA-N 1,4-dimethoxyanthracene-9,10-dicarbaldehyde Chemical compound C1=CC=C2C(C=O)=C3C(OC)=CC=C(OC)C3=C(C=O)C2=C1 FLNHUGMJJMGODI-UHFFFAOYSA-N 0.000 description 2
- VQBRTNVYEIZVMP-UHFFFAOYSA-N 1,4-dimethylanthracene Chemical compound C1=CC=C2C=C3C(C)=CC=C(C)C3=CC2=C1 VQBRTNVYEIZVMP-UHFFFAOYSA-N 0.000 description 2
- HWFIOXSONIVHRD-UHFFFAOYSA-N 1-(4,5-dihydro-1h-imidazol-2-yl)-1-methylhydrazine;hydroiodide Chemical compound I.CN(N)C1=NCCN1 HWFIOXSONIVHRD-UHFFFAOYSA-N 0.000 description 2
- SQRXDDXPBMBWJJ-UHFFFAOYSA-N 1-chloro-9,10-dihydroanthracene-9,10-dicarbaldehyde Chemical compound O=CC1C2=CC=CC=C2C(C=O)C2=C1C=CC=C2Cl SQRXDDXPBMBWJJ-UHFFFAOYSA-N 0.000 description 2
- SRIHSAFSOOUEGL-UHFFFAOYSA-N 1-chloroanthracene Chemical compound C1=CC=C2C=C3C(Cl)=CC=CC3=CC2=C1 SRIHSAFSOOUEGL-UHFFFAOYSA-N 0.000 description 2
- FVIPQYRQVMAEEN-UHFFFAOYSA-N 1-chloroanthracene-9,10-dicarbaldehyde Chemical compound C1=CC=C2C(C=O)=C3C(Cl)=CC=CC3=C(C=O)C2=C1 FVIPQYRQVMAEEN-UHFFFAOYSA-N 0.000 description 2
- HYFLWBNQFMXCPA-UHFFFAOYSA-N 1-ethyl-2-methylbenzene Chemical compound CCC1=CC=CC=C1C HYFLWBNQFMXCPA-UHFFFAOYSA-N 0.000 description 2
- KEOXCDRNOOSMJU-UHFFFAOYSA-N 1-methylanthracene-9,10-dicarbaldehyde Chemical compound C1=CC=C2C(C=O)=C3C(C)=CC=CC3=C(C=O)C2=C1 KEOXCDRNOOSMJU-UHFFFAOYSA-N 0.000 description 2
- UOMRYVQGFQRNFV-UHFFFAOYSA-N 2,6-dichloroanthracene-9,10-dicarbaldehyde Chemical compound C1=C(Cl)C=CC2=C(C=O)C3=CC(Cl)=CC=C3C(C=O)=C21 UOMRYVQGFQRNFV-UHFFFAOYSA-N 0.000 description 2
- NBSHFBANNVIIGL-UHFFFAOYSA-N 2-chloro-9,10-dihydroanthracene-9,10-dicarbaldehyde Chemical compound C1=CC=C2C(C=O)C3=CC(Cl)=CC=C3C(C=O)C2=C1 NBSHFBANNVIIGL-UHFFFAOYSA-N 0.000 description 2
- OWFINXQLBMJDJQ-UHFFFAOYSA-N 2-chloroanthracene Chemical compound C1=CC=CC2=CC3=CC(Cl)=CC=C3C=C21 OWFINXQLBMJDJQ-UHFFFAOYSA-N 0.000 description 2
- NLAMRHVJAKNLTM-UHFFFAOYSA-N 2-ethylanthracene-9,10-dicarbaldehyde Chemical compound C1=CC=CC2=C(C=O)C3=CC(CC)=CC=C3C(C=O)=C21 NLAMRHVJAKNLTM-UHFFFAOYSA-N 0.000 description 2
- RQNKXAIJVOBSJY-UHFFFAOYSA-N 2-methyl-9,10-dihydroanthracene-9,10-dicarbaldehyde Chemical compound C1=CC=C2C(C=O)C3=CC(C)=CC=C3C(C=O)C2=C1 RQNKXAIJVOBSJY-UHFFFAOYSA-N 0.000 description 2
- WIPKZLIKOXLWCF-UHFFFAOYSA-N 4,5-dihydro-1h-imidazol-2-ylhydrazine Chemical compound NNC1=NCCN1 WIPKZLIKOXLWCF-UHFFFAOYSA-N 0.000 description 2
- MKTIQGSWGWAWKH-UHFFFAOYSA-N 4,5-dimethyltetracyclo[6.6.2.02,7.09,14]hexadeca-2(7),3,5,9,11,13-hexaene-15,16-diol Chemical compound C12=CC=CC=C2C2C(C=C(C(=C3)C)C)=C3C1C(O)C2O MKTIQGSWGWAWKH-UHFFFAOYSA-N 0.000 description 2
- KEPZBZAZDOOJTJ-UHFFFAOYSA-N 4-chlorotetracyclo[6.6.2.02,7.09,14]hexadeca-2(7),3,5,9,11,13-hexaene-15,16-diol Chemical compound C12=CC=C(Cl)C=C2C2C(O)C(O)C1C1=CC=CC=C12 KEPZBZAZDOOJTJ-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- AJMYINBVZILSBW-UHFFFAOYSA-N 9,10-bis(chloromethyl)-2-methylanthracene Chemical compound C1=CC=CC2=C(CCl)C3=CC(C)=CC=C3C(CCl)=C21 AJMYINBVZILSBW-UHFFFAOYSA-N 0.000 description 2
- UOSROERWQJTVNU-UHFFFAOYSA-N 9,10-bis(chloromethyl)anthracene Chemical class C1=CC=C2C(CCl)=C(C=CC=C3)C3=C(CCl)C2=C1 UOSROERWQJTVNU-UHFFFAOYSA-N 0.000 description 2
- KNHHFDCLCNKUBD-UHFFFAOYSA-N 9,10-dihydroanthracene-9,10-dicarbaldehyde Chemical compound C1=CC=C2C(C=O)C3=CC=CC=C3C(C=O)C2=C1 KNHHFDCLCNKUBD-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 241000588915 Klebsiella aerogenes Species 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 241000186359 Mycobacterium Species 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 241000588767 Proteus vulgaris Species 0.000 description 2
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 241000220317 Rosa Species 0.000 description 2
- 235000014548 Rubus moluccanus Nutrition 0.000 description 2
- 241001354013 Salmonella enterica subsp. enterica serovar Enteritidis Species 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-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
- 241000193996 Streptococcus pyogenes Species 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 125000005577 anthracene group Chemical group 0.000 description 2
- APAJFZPFBHMFQR-UHFFFAOYSA-N anthraflavic acid Chemical compound OC1=CC=C2C(=O)C3=CC(O)=CC=C3C(=O)C2=C1 APAJFZPFBHMFQR-UHFFFAOYSA-N 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 239000003429 antifungal agent Substances 0.000 description 2
- 229940121375 antifungal agent Drugs 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
- 229940117975 chromium trioxide Drugs 0.000 description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 239000002612 dispersion medium Substances 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002081 enamines Chemical class 0.000 description 2
- 229940092559 enterobacter aerogenes Drugs 0.000 description 2
- 230000009969 flowable effect Effects 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 150000007857 hydrazones Chemical class 0.000 description 2
- 238000002513 implantation Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 239000007951 isotonicity adjuster Substances 0.000 description 2
- 239000004310 lactic acid Substances 0.000 description 2
- 235000014655 lactic acid Nutrition 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- 230000000527 lymphocytic effect Effects 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 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 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000006916 nutrient agar Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 229920002866 paraformaldehyde Polymers 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000013641 positive control Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 229940007042 proteus vulgaris Drugs 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 229910052702 rhenium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 238000003892 spreading Methods 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 2
- MLIWQXBKMZNZNF-KUHOPJCQSA-N (2e)-2,6-bis[(4-azidophenyl)methylidene]-4-methylcyclohexan-1-one Chemical compound O=C1\C(=C\C=2C=CC(=CC=2)N=[N+]=[N-])CC(C)CC1=CC1=CC=C(N=[N+]=[N-])C=C1 MLIWQXBKMZNZNF-KUHOPJCQSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- RHUYHJGZWVXEHW-UHFFFAOYSA-N 1,1-Dimethyhydrazine Chemical compound CN(C)N RHUYHJGZWVXEHW-UHFFFAOYSA-N 0.000 description 1
- BKCBIZNLIMHERY-UHFFFAOYSA-N 1,2-dihydroxyanthracene-9,10-dicarbaldehyde;dihydrochloride Chemical compound Cl.Cl.C1=CC=CC2=C(C=O)C3=C(O)C(O)=CC=C3C(C=O)=C21 BKCBIZNLIMHERY-UHFFFAOYSA-N 0.000 description 1
- TZAWNLPUTOWENL-UHFFFAOYSA-N 1,4,5,6-tetrahydropyrimidin-2-ylhydrazine;hydroiodide Chemical compound I.NNC1=NCCCN1 TZAWNLPUTOWENL-UHFFFAOYSA-N 0.000 description 1
- LEHBETWUJUBURQ-UHFFFAOYSA-N 1,4-dihydroxyanthracene-9,10-dicarbaldehyde Chemical compound C1=CC=C2C(C=O)=C3C(O)=CC=C(O)C3=C(C=O)C2=C1 LEHBETWUJUBURQ-UHFFFAOYSA-N 0.000 description 1
- FIVASPGBCSGVSH-UHFFFAOYSA-N 1,4-dihydroxyanthracene-9,10-dicarbaldehyde;dihydrochloride Chemical compound Cl.Cl.C1=CC=C2C(C=O)=C3C(O)=CC=C(O)C3=C(C=O)C2=C1 FIVASPGBCSGVSH-UHFFFAOYSA-N 0.000 description 1
- FIDJTLCYAKXXFY-UHFFFAOYSA-N 1,4-dimethoxy-9,10-dihydroanthracene-9,10-dicarbaldehyde Chemical compound O=CC1C2=CC=CC=C2C(C=O)C2=C1C(OC)=CC=C2OC FIDJTLCYAKXXFY-UHFFFAOYSA-N 0.000 description 1
- SXCJVHHMOMCOFH-UHFFFAOYSA-N 1,4-dimethylanthracene-9,10-dicarbaldehyde;dihydrochloride Chemical compound Cl.Cl.C1=CC=C2C(C=O)=C3C(C)=CC=C(C)C3=C(C=O)C2=C1 SXCJVHHMOMCOFH-UHFFFAOYSA-N 0.000 description 1
- KZNJSFHJUQDYHE-UHFFFAOYSA-N 1-methylanthracene Chemical compound C1=CC=C2C=C3C(C)=CC=CC3=CC2=C1 KZNJSFHJUQDYHE-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- RNSSXMLLVVEBBV-UHFFFAOYSA-N 10-(hydroxymethyl)anthracene-9-carbaldehyde Chemical compound C1=CC=C2C(CO)=C(C=CC=C3)C3=C(C=O)C2=C1 RNSSXMLLVVEBBV-UHFFFAOYSA-N 0.000 description 1
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 1
- VCDFVPDREZWQJO-UHFFFAOYSA-N 2,6-dichloroanthracene Chemical compound C1=C(Cl)C=CC2=CC3=CC(Cl)=CC=C3C=C21 VCDFVPDREZWQJO-UHFFFAOYSA-N 0.000 description 1
- HPJGQKYDOKIOID-UHFFFAOYSA-N 2,6-dichloroanthracene-9,10-dicarbaldehyde;dihydrochloride Chemical compound Cl.Cl.C1=C(Cl)C=CC2=C(C=O)C3=CC(Cl)=CC=C3C(C=O)=C21 HPJGQKYDOKIOID-UHFFFAOYSA-N 0.000 description 1
- QMOOQYLCKPENSJ-UHFFFAOYSA-N 2,6-difluoroanthracene Chemical compound C1=C(F)C=CC2=CC3=CC(F)=CC=C3C=C21 QMOOQYLCKPENSJ-UHFFFAOYSA-N 0.000 description 1
- LIGKRPDFPAXHET-UHFFFAOYSA-N 2,6-dimethoxyanthracene-9,10-dicarbaldehyde Chemical compound C1=C(OC)C=CC2=C(C=O)C3=CC(OC)=CC=C3C(C=O)=C21 LIGKRPDFPAXHET-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- XOGPDSATLSAZEK-UHFFFAOYSA-N 2-Aminoanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(N)=CC=C3C(=O)C2=C1 XOGPDSATLSAZEK-UHFFFAOYSA-N 0.000 description 1
- XLQUERJWQIWQEG-UHFFFAOYSA-N 2-aminoanthracene-9,10-dicarbaldehyde;dihydrochloride Chemical compound Cl.Cl.C1=CC=CC2=C(C=O)C3=CC(N)=CC=C3C(C=O)=C21 XLQUERJWQIWQEG-UHFFFAOYSA-N 0.000 description 1
- MCLQQCXMIWKKDM-UHFFFAOYSA-N 2-chloroanthracene-9,10-dicarbaldehyde;dihydrochloride Chemical compound Cl.Cl.C1=CC=CC2=C(C=O)C3=CC(Cl)=CC=C3C(C=O)=C21 MCLQQCXMIWKKDM-UHFFFAOYSA-N 0.000 description 1
- MNNZINNZIQVULG-UHFFFAOYSA-N 2-chloroethylbenzene Chemical compound ClCCC1=CC=CC=C1 MNNZINNZIQVULG-UHFFFAOYSA-N 0.000 description 1
- ZXAGXLDEMUNQSH-UHFFFAOYSA-N 2-ethylanthracene Chemical compound C1=CC=CC2=CC3=CC(CC)=CC=C3C=C21 ZXAGXLDEMUNQSH-UHFFFAOYSA-N 0.000 description 1
- RANPFCAMPOUOHI-UHFFFAOYSA-N 2-hydroxyanthracene-9,10-dicarbaldehyde;dihydrochloride Chemical compound Cl.Cl.C1=CC=CC2=C(C=O)C3=CC(O)=CC=C3C(C=O)=C21 RANPFCAMPOUOHI-UHFFFAOYSA-N 0.000 description 1
- NJDYOZOOLZHHKE-UHFFFAOYSA-N 2-methylanthracene-9,10-dicarbaldehyde;hydrate;dihydrochloride Chemical compound O.Cl.Cl.C1=CC=CC2=C(C=O)C3=CC(C)=CC=C3C(C=O)=C21 NJDYOZOOLZHHKE-UHFFFAOYSA-N 0.000 description 1
- AYWTZYSQABXDEA-UHFFFAOYSA-N 2-methylsulfanyl-4,5-dihydro-1H-imidazole dihydroiodide Chemical compound I.I.CSC=1NCCN1 AYWTZYSQABXDEA-UHFFFAOYSA-N 0.000 description 1
- FGLBSLMDCBOPQK-UHFFFAOYSA-N 2-nitropropane Chemical compound CC(C)[N+]([O-])=O FGLBSLMDCBOPQK-UHFFFAOYSA-N 0.000 description 1
- ZDOYCFMMWXWMQG-UHFFFAOYSA-N 3,6-dimethoxytetracyclo[6.6.2.02,7.09,14]hexadeca-1,3,5,7,9,11,13-heptaene-15,16-diol Chemical class C12=CC=CC=C2C2=C3C(OC)=CC=C(OC)C3=C1C(O)C2O ZDOYCFMMWXWMQG-UHFFFAOYSA-N 0.000 description 1
- HEINYDLYAKOQLO-UHFFFAOYSA-N 3,6-dimethoxytetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaene-15,16-diol Chemical compound C12=CC=CC=C2C2C(C(OC)=CC=C3OC)=C3C1C(O)C2O HEINYDLYAKOQLO-UHFFFAOYSA-N 0.000 description 1
- PIGMDMCUDORLRI-UHFFFAOYSA-N 3,6-dimethyltetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaene-15,16-diol Chemical compound C12=CC=CC=C2C2C(C(C)=CC=C3C)=C3C1C(O)C2O PIGMDMCUDORLRI-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- ORDLJERQKZRBRZ-UHFFFAOYSA-N 4,5-dihydro-1h-imidazol-2-ylhydrazine;hydrochloride Chemical compound Cl.NNC1=NCCN1 ORDLJERQKZRBRZ-UHFFFAOYSA-N 0.000 description 1
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
- MBVFRSJFKMJRHA-UHFFFAOYSA-N 4-fluoro-1-benzofuran-7-carbaldehyde Chemical compound FC1=CC=C(C=O)C2=C1C=CO2 MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 description 1
- YJKPQSCFVMCKLW-UHFFFAOYSA-N 4-methyltetracyclo[6.6.2.02,7.09,14]hexadeca-1,3,5,7,9,11,13-heptaene-15,16-diol Chemical class C1=CC=CC2=C(C(O)C3O)C4=CC=C(C)C=C4C3=C21 YJKPQSCFVMCKLW-UHFFFAOYSA-N 0.000 description 1
- 206010003445 Ascites Diseases 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- HPHVOCXDWMOJQK-UHFFFAOYSA-N C12=CC=CC=C2C(C=NNC=2NCCN=2)=C2C=C(C)C(C)=CC2=C1C=NNC1=NCCN1 Chemical compound C12=CC=CC=C2C(C=NNC=2NCCN=2)=C2C=C(C)C(C)=CC2=C1C=NNC1=NCCN1 HPHVOCXDWMOJQK-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZXHCELNAGWSSDI-UHFFFAOYSA-N Cl.Cl.COC1=CC=C(C2=C(C3=CC=CC=C3C(=C12)C=O)C=O)OC Chemical compound Cl.Cl.COC1=CC=C(C2=C(C3=CC=CC=C3C(=C12)C=O)C=O)OC ZXHCELNAGWSSDI-UHFFFAOYSA-N 0.000 description 1
- ZNLSITYQMSUZCM-UHFFFAOYSA-N ClC1(C(C2=CC3=CC=C(C=C3C=C2C=C1)Cl)C=O)C=O Chemical compound ClC1(C(C2=CC3=CC=C(C=C3C=C2C=C1)Cl)C=O)C=O ZNLSITYQMSUZCM-UHFFFAOYSA-N 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 1
- 241000194033 Enterococcus Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- 241000588748 Klebsiella Species 0.000 description 1
- 241000588747 Klebsiella pneumoniae Species 0.000 description 1
- 208000007093 Leukemia L1210 Diseases 0.000 description 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- MJOQJPYNENPSSS-XQHKEYJVSA-N [(3r,4s,5r,6s)-4,5,6-triacetyloxyoxan-3-yl] acetate Chemical compound CC(=O)O[C@@H]1CO[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O MJOQJPYNENPSSS-XQHKEYJVSA-N 0.000 description 1
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
- 239000003070 absorption delaying agent Substances 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- KWPWOLSPBFBUIM-UHFFFAOYSA-N anthracene-1,2-dicarbaldehyde;dihydrochloride Chemical compound Cl.Cl.C1=CC=CC2=CC3=C(C=O)C(C=O)=CC=C3C=C21 KWPWOLSPBFBUIM-UHFFFAOYSA-N 0.000 description 1
- PLOXNKMDKXVFCO-UHFFFAOYSA-N anthracene-9,10-dicarbaldehyde;dihydroiodide Chemical compound I.I.C1=CC=C2C(C=O)=C(C=CC=C3)C3=C(C=O)C2=C1 PLOXNKMDKXVFCO-UHFFFAOYSA-N 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229960004926 chlorobutanol Drugs 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- UGMCXQCYOVCMTB-UHFFFAOYSA-K dihydroxy(stearato)aluminium Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[Al](O)O UGMCXQCYOVCMTB-UHFFFAOYSA-K 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- GZRYBYIBLHMWCD-UHFFFAOYSA-N dimethyl(methylidene)-$l^{4}-sulfane Chemical compound CS(C)=C GZRYBYIBLHMWCD-UHFFFAOYSA-N 0.000 description 1
- DKWOHBPRFZIUQL-UHFFFAOYSA-N dimethyl-methylidene-oxo-$l^{6}-sulfane Chemical compound C[S+](C)([CH2-])=O DKWOHBPRFZIUQL-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000005597 hydrazone group Chemical group 0.000 description 1
- 229960000443 hydrochloric acid Drugs 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- KQSBZNJFKWOQQK-UHFFFAOYSA-N hystazarin Natural products O=C1C2=CC=CC=C2C(=O)C2=C1C=C(O)C(O)=C2 KQSBZNJFKWOQQK-UHFFFAOYSA-N 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000007972 injectable composition Substances 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 229940087875 leukine Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- MHCFAGZWMAWTNR-UHFFFAOYSA-M lithium perchlorate Chemical compound [Li+].[O-]Cl(=O)(=O)=O MHCFAGZWMAWTNR-UHFFFAOYSA-M 0.000 description 1
- 229910001486 lithium perchlorate Inorganic materials 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 201000005296 lung carcinoma Diseases 0.000 description 1
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 1
- 229910001623 magnesium bromide Inorganic materials 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 230000036210 malignancy Effects 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- CZXGXYBOQYQXQD-UHFFFAOYSA-N methyl benzenesulfonate Chemical compound COS(=O)(=O)C1=CC=CC=C1 CZXGXYBOQYQXQD-UHFFFAOYSA-N 0.000 description 1
- 229960001156 mitoxantrone Drugs 0.000 description 1
- 230000002969 morbid Effects 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000012285 osmium tetroxide Substances 0.000 description 1
- 229910000489 osmium tetroxide Inorganic materials 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 229960003742 phenol Drugs 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- GUEIZVNYDFNHJU-UHFFFAOYSA-N quinizarin Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2O GUEIZVNYDFNHJU-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 108010038379 sargramostim Proteins 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- WFPLAJXRAXPRJY-UHFFFAOYSA-J tetralithium tetraacetate Chemical compound C(C)(=O)[O-].C(C)(=O)[O-].C(C)(=O)[O-].C(C)(=O)[O-].[Li+].[Li+].[Li+].[Li+] WFPLAJXRAXPRJY-UHFFFAOYSA-J 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- 239000001974 tryptic soy broth Substances 0.000 description 1
- 108010050327 trypticase-soy broth Proteins 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000009777 vacuum freeze-drying Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/42—Radicals substituted by singly-bound nitrogen atoms having hetero atoms attached to the substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/32—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by introduction of halogenated alkyl groups into ring compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/095—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of organic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/38—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings
- C07C47/453—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/38—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings
- C07C47/457—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/38—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings
- C07C47/47—Unsaturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/546—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/55—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/56—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing hydroxy groups
- C07C47/57—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing hydroxy groups polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/76—Nitrogen atoms to which a second hetero atom is attached
- C07D213/77—Hydrazine radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
- C07D233/52—Nitrogen atoms not forming part of a nitro radical with hetero atoms directly attached to said nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D239/08—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms directly attached in position 2
- C07D239/12—Nitrogen atoms not forming part of a nitro radical
- C07D239/18—Nitrogen atoms not forming part of a nitro radical with hetero atoms attached to said nitrogen atoms, except nitro radicals, e.g. hydrazine radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/04—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D245/00—Heterocyclic compounds containing rings of more than seven members having two nitrogen atoms as the only ring hetero atoms
- C07D245/02—Heterocyclic compounds containing rings of more than seven members having two nitrogen atoms as the only ring hetero atoms not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
- C07D317/64—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/70—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with ring systems containing two or more relevant rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/09—Geometrical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/24—Anthracenes; Hydrogenated anthracenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/86—Ring systems containing bridged rings containing four rings
- C07C2603/88—Ethanoanthracenes; Hydrogenated ethanoanthracenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/90—Ring systems containing bridged rings containing more than four rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US85514677A | 1977-11-28 | 1977-11-28 | |
US85514677 | 1977-11-28 | ||
US93959178A | 1978-09-05 | 1978-09-05 | |
US93959178 | 1978-09-05 | ||
US05/943,908 US4235996A (en) | 1978-09-19 | 1978-09-19 | Bis(2-imidazolin-2-ylhydrazone)-9,10-dihydro-9,10-anthracenedicarboxaldehydes |
US94390878 | 1978-09-19 | ||
US05/947,976 US4187373A (en) | 1978-10-02 | 1978-10-02 | Novel dihydrobenzanthracene derivatives |
US94797678 | 1978-10-02 |
Publications (3)
Publication Number | Publication Date |
---|---|
FI783621A7 FI783621A7 (fi) | 1979-05-29 |
FI71726B FI71726B (fi) | 1986-10-31 |
FI71726C true FI71726C (fi) | 1987-02-09 |
Family
ID=27505921
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FI783621A FI71726C (fi) | 1977-11-28 | 1978-11-27 | Foerfarande foer framstaellning av terapeutiskt anvaendbara antracen-9,10-bis-karbonylderivat. |
Country Status (13)
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4258181A (en) * | 1978-09-05 | 1981-03-24 | American Cyanamid Company | Substituted 9,10-anthracenebishydrazones |
US4275010A (en) * | 1979-10-24 | 1981-06-23 | American Cyanamid Company | 5,8-Dihydroxy-1,4-bis(guanidinylamino)anthraquinones |
IL84213A (en) * | 1986-10-23 | 1992-09-06 | American Cyanamid Co | N-acylated derivatives of bisanthrene,process for their preparation and pharmaceutical compositions containing them |
DE4013023A1 (de) * | 1990-04-24 | 1991-11-07 | Lohmann Rudolf Lomapharm | Verwendung von anthrachinonderivaten zur prophylaxe und therapie von viruserkrankungen |
JP6443741B2 (ja) * | 2014-12-12 | 2018-12-26 | 川崎化成工業株式会社 | 光ラジカル重合開始剤 |
WO2021016464A1 (en) * | 2019-07-23 | 2021-01-28 | City Of Hope | Methods and compositions for treating cancer |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2857434A (en) * | 1956-10-04 | 1958-10-21 | Monsanto Chemicals | Dihydroanthracenedicarboxaldehydes and process of preparing |
-
1978
- 1978-11-06 GB GB7843300A patent/GB2009171B/en not_active Expired
- 1978-11-22 NZ NZ188984A patent/NZ188984A/xx unknown
- 1978-11-23 DE DE19782850822 patent/DE2850822A1/de active Granted
- 1978-11-27 IT IT52073/78A patent/IT1157724B/it active
- 1978-11-27 NO NO783985A patent/NO152556C/no unknown
- 1978-11-27 FI FI783621A patent/FI71726C/fi not_active IP Right Cessation
- 1978-11-27 AR AR275590A patent/AR228126A1/es active
- 1978-11-27 SE SE7812198A patent/SE449610B/sv not_active IP Right Cessation
- 1978-11-27 CH CH1212678A patent/CH645094A5/de not_active IP Right Cessation
- 1978-11-27 AT AT0845978A patent/AT363928B/de not_active IP Right Cessation
- 1978-11-27 IE IE2342/78A patent/IE47633B1/en unknown
- 1978-11-28 DD DD78209365A patent/DD140250A5/de not_active IP Right Cessation
-
1984
- 1984-07-26 HK HK577/84A patent/HK57784A/xx not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
CH645094A5 (de) | 1984-09-14 |
HK57784A (en) | 1984-08-03 |
FI783621A7 (fi) | 1979-05-29 |
ATA845978A (de) | 1981-02-15 |
IT7852073A0 (it) | 1978-11-27 |
SE7812198L (sv) | 1979-05-29 |
DD140250A5 (de) | 1980-02-20 |
NZ188984A (en) | 1981-12-15 |
GB2009171A (en) | 1979-06-13 |
FI71726B (fi) | 1986-10-31 |
IE47633B1 (en) | 1984-05-16 |
AR228126A1 (es) | 1983-01-31 |
SE449610B (sv) | 1987-05-11 |
DE2850822A1 (de) | 1979-05-31 |
NO152556B (no) | 1985-07-08 |
AT363928B (de) | 1981-09-10 |
NO152556C (no) | 1985-10-16 |
NO783985L (no) | 1979-05-29 |
IE782342L (en) | 1979-05-28 |
DE2850822C2 (enrdf_load_stackoverflow) | 1991-11-28 |
IT1157724B (it) | 1987-02-18 |
GB2009171B (en) | 1982-08-18 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Murdock et al. | Antitumor agents. II. Bis (guanylhydrazones) of anthracene-9, 10-dicarboxaldehydes | |
JPS6089474A (ja) | モルフイナン誘導体,その製造方法,及び該化合物を含有する抗腫瘍剤 | |
US5834462A (en) | Tricyclic heterocyclic sulfonamide and sulfonic ester derivatives | |
JPS63104963A (ja) | 5−ニトロベンゾ〔de〕イソキノリン−1,3−ジオンの製法 | |
FI66868C (fi) | Foerfarande foer framstaellning av imidazo(1,2-a)kinoxalinmetanoler anvaendbara saosom laekemedel | |
FI70882B (fi) | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara antrakinonderivat | |
FI71726C (fi) | Foerfarande foer framstaellning av terapeutiskt anvaendbara antracen-9,10-bis-karbonylderivat. | |
US20210040121A1 (en) | Fused polycyclic dimers | |
HUT75121A (en) | Bis-imide derivatives of tri-and tetraamines and pharmaceutical compositions containing them | |
SU575031A3 (ru) | Способ получени конденсированных трициклических производных имидазола или их солей | |
US5747502A (en) | Process for preparing benzo c!phenanthridinium derivatives, novel compounds prepared by said process, and antitumor agents | |
JPS61112061A (ja) | 新規なフエナジン誘導体 | |
Sarma et al. | Synthesis of novel aminoquinonoid analogues of diospyrin and evaluation of their inhibitory activity against murine and human cancer cells | |
CN109438323A (zh) | 一类具有抗肿瘤活性的棉酚-靛红席夫碱类化合物及其合成方法 | |
IE56782B1 (en) | Substituted anthra(1,9-cd)pyrazol-6(2h)-ones | |
US3914264A (en) | 2-Lower alkoxy-3-(lower alkylthio)-1,4-naphthoquinone | |
US4100277A (en) | 4,1-Benzoxazonine derivatives and process therefor | |
US6162822A (en) | Bisimide compounds | |
US3932512A (en) | Antiviral 1,2,3,4-tetrahydro-1,-alkano naphthalenamine derivatives | |
US4187373A (en) | Novel dihydrobenzanthracene derivatives | |
DK168333B1 (da) | Analogifremgangsmåde til fremstilling af anthracen-9,10-bis-carbonylhydrazoner og derivater eller salte deraf | |
FR2572285A1 (fr) | Medicaments a base de nouveaux derives de la phenethylaminoalcoyle-6 furo-(3,4-c)-pyridine | |
CS195343B2 (en) | Method of producing derivatives of dimere indol-dihydro-indoldiones | |
AU2014207125B2 (en) | Helquat derivatives, preparation thereof, and use thereof as medicaments | |
CN108892634B (zh) | 一种吲哚甲基苯胺类化合物及其应用 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
MA | Patent expired | ||
MM | Patent lapsed | ||
FD | Application lapsed | ||
MA | Patent expired |
Owner name: AMERICAN CYANAMID COMPANY |