CS178691A3 - Heterocyclic anthracyclinone and anthracycline analogs - Google Patents
Heterocyclic anthracyclinone and anthracycline analogs Download PDFInfo
- Publication number
- CS178691A3 CS178691A3 CS911786A CS178691A CS178691A3 CS 178691 A3 CS178691 A3 CS 178691A3 CS 911786 A CS911786 A CS 911786A CS 178691 A CS178691 A CS 178691A CS 178691 A3 CS178691 A3 CS 178691A3
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- Czechoslovakia
- Prior art keywords
- compound
- formula
- group
- carbon atoms
- dioxo
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- 229940045799 anthracyclines and related substance Drugs 0.000 title claims description 16
- 125000000623 heterocyclic group Chemical group 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims description 516
- 239000000203 mixture Substances 0.000 claims description 189
- 125000004432 carbon atom Chemical group C* 0.000 claims description 149
- -1 leuoine Chemical compound 0.000 claims description 134
- 125000003118 aryl group Chemical group 0.000 claims description 97
- 238000000034 method Methods 0.000 claims description 94
- 125000000217 alkyl group Chemical group 0.000 claims description 86
- 206010028980 Neoplasm Diseases 0.000 claims description 80
- 239000002904 solvent Substances 0.000 claims description 78
- 238000006243 chemical reaction Methods 0.000 claims description 76
- 229910052739 hydrogen Inorganic materials 0.000 claims description 69
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 69
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 62
- 239000001257 hydrogen Substances 0.000 claims description 61
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 59
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 59
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 46
- 125000002252 acyl group Chemical group 0.000 claims description 44
- 125000003277 amino group Chemical group 0.000 claims description 44
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 42
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 37
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 31
- 150000002148 esters Chemical class 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 27
- 239000003795 chemical substances by application Substances 0.000 claims description 27
- 238000002360 preparation method Methods 0.000 claims description 27
- 125000006239 protecting group Chemical group 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 25
- AKHSBAVQPIRVAG-UHFFFAOYSA-N 4h-isochromene-1,3-dione Chemical compound C1=CC=C2C(=O)OC(=O)CC2=C1 AKHSBAVQPIRVAG-UHFFFAOYSA-N 0.000 claims description 24
- 201000011510 cancer Diseases 0.000 claims description 24
- 229910052799 carbon Inorganic materials 0.000 claims description 24
- 125000004494 ethyl ester group Chemical group 0.000 claims description 24
- 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 23
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 23
- 125000004429 atom Chemical group 0.000 claims description 23
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 23
- 235000019253 formic acid Nutrition 0.000 claims description 23
- 125000005843 halogen group Chemical group 0.000 claims description 21
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 21
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 20
- 239000008194 pharmaceutical composition Substances 0.000 claims description 19
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 18
- 230000000259 anti-tumor effect Effects 0.000 claims description 18
- 125000001153 fluoro group Chemical group F* 0.000 claims description 18
- 150000004702 methyl esters Chemical class 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 18
- 239000003814 drug Substances 0.000 claims description 17
- 230000008569 process Effects 0.000 claims description 17
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 238000011282 treatment Methods 0.000 claims description 15
- 239000003937 drug carrier Substances 0.000 claims description 13
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims description 13
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 12
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 12
- 235000001014 amino acid Nutrition 0.000 claims description 12
- 150000001413 amino acids Chemical class 0.000 claims description 12
- 230000001093 anti-cancer Effects 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 10
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 10
- 150000001720 carbohydrates Chemical class 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- 150000002576 ketones Chemical class 0.000 claims description 9
- 235000000346 sugar Nutrition 0.000 claims description 9
- 229940124597 therapeutic agent Drugs 0.000 claims description 9
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 241000124008 Mammalia Species 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 8
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 239000003153 chemical reaction reagent Substances 0.000 claims description 8
- 229910003002 lithium salt Inorganic materials 0.000 claims description 8
- 159000000002 lithium salts Chemical class 0.000 claims description 8
- 230000003647 oxidation Effects 0.000 claims description 8
- 238000007254 oxidation reaction Methods 0.000 claims description 8
- 230000001590 oxidative effect Effects 0.000 claims description 8
- LZNNMMKMGKFYLL-UHFFFAOYSA-N 2h-pyran-3-carboxylic acid Chemical compound OC(=O)C1=CC=COC1 LZNNMMKMGKFYLL-UHFFFAOYSA-N 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 7
- 125000003435 aroyl group Chemical group 0.000 claims description 7
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- 239000011593 sulfur Substances 0.000 claims description 7
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 7
- OTLNPYWUJOZPPA-UHFFFAOYSA-M 4-nitrobenzoate Chemical compound [O-]C(=O)C1=CC=C([N+]([O-])=O)C=C1 OTLNPYWUJOZPPA-UHFFFAOYSA-M 0.000 claims description 6
- 239000004475 Arginine Substances 0.000 claims description 6
- 239000004471 Glycine Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims description 6
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 6
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 6
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims description 6
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 6
- 239000004472 Lysine Substances 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 6
- 235000004279 alanine Nutrition 0.000 claims description 6
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 6
- 235000009697 arginine Nutrition 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims description 6
- 235000018417 cysteine Nutrition 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 229930182817 methionine Natural products 0.000 claims description 6
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 claims description 6
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- LZPBKINTWROMEA-UHFFFAOYSA-N tetracene-5,12-dione Chemical compound C1=CC=C2C=C3C(=O)C4=CC=CC=C4C(=O)C3=CC2=C1 LZPBKINTWROMEA-UHFFFAOYSA-N 0.000 claims description 6
- 125000000101 thioether group Chemical group 0.000 claims description 6
- HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical compound O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 claims description 5
- FEWRVBVKPCBBRF-UHFFFAOYSA-N 3,4-dihydro-1h-isochromen-1-ol Chemical compound C1=CC=C2C(O)OCCC2=C1 FEWRVBVKPCBBRF-UHFFFAOYSA-N 0.000 claims description 5
- 150000001241 acetals Chemical class 0.000 claims description 5
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 5
- 235000014633 carbohydrates Nutrition 0.000 claims description 5
- 239000013522 chelant Substances 0.000 claims description 5
- 238000010511 deprotection reaction Methods 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 238000005858 glycosidation reaction Methods 0.000 claims description 5
- 230000007062 hydrolysis Effects 0.000 claims description 5
- 238000006460 hydrolysis reaction Methods 0.000 claims description 5
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 230000017693 oxidative demethylation Effects 0.000 claims description 5
- 238000007067 oxidative demethylation reaction Methods 0.000 claims description 5
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 5
- 238000007363 ring formation reaction Methods 0.000 claims description 5
- 150000008163 sugars Chemical class 0.000 claims description 5
- ATPYMFXOZQEWIG-LFRDXLMFSA-N (2s,5r,6s)-5,6-dihydroxy-2-methyloxan-3-one Chemical compound C[C@@H]1O[C@H](O)[C@H](O)CC1=O ATPYMFXOZQEWIG-LFRDXLMFSA-N 0.000 claims description 4
- JWFRNGYBHLBCMB-HCWXCVPCSA-N (3s,4r,5s)-3,4,5-trihydroxyhexanal Chemical compound C[C@H](O)[C@@H](O)[C@@H](O)CC=O JWFRNGYBHLBCMB-HCWXCVPCSA-N 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- XXIHHRIZGBRENI-RITPCOANSA-N amicetose Chemical compound C[C@@H](O)[C@@H](O)CCC=O XXIHHRIZGBRENI-RITPCOANSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 108090000623 proteins and genes Proteins 0.000 claims description 4
- 150000003573 thiols Chemical group 0.000 claims description 4
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 4
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 claims description 4
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 3
- NYJBTJMNTNCTCP-UHFFFAOYSA-N 2,5-dimethoxybenzoic acid Chemical compound COC1=CC=C(OC)C(C(O)=O)=C1 NYJBTJMNTNCTCP-UHFFFAOYSA-N 0.000 claims description 3
- XXIHHRIZGBRENI-WDSKDSINSA-N L-rhodinose Chemical compound C[C@H](O)[C@@H](O)CCC=O XXIHHRIZGBRENI-WDSKDSINSA-N 0.000 claims description 3
- 239000002841 Lewis acid Substances 0.000 claims description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical group OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
- 150000007517 lewis acids Chemical class 0.000 claims description 3
- 239000002502 liposome Substances 0.000 claims description 3
- 235000018102 proteins Nutrition 0.000 claims description 3
- 102000004169 proteins and genes Human genes 0.000 claims description 3
- 230000009467 reduction Effects 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 230000008685 targeting Effects 0.000 claims description 3
- OFQZALLOGGRSBM-UHFFFAOYSA-N (4-nitrophenyl)methyl formate Chemical compound [O-][N+](=O)C1=CC=C(COC=O)C=C1 OFQZALLOGGRSBM-UHFFFAOYSA-N 0.000 claims description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
- HHZHOOXEMGLCJA-UHFFFAOYSA-N 1-(1-hydroxy-5,8-dimethoxy-3,4-dihydro-1h-isochromen-3-yl)ethanone Chemical compound OC1OC(C(C)=O)CC2=C1C(OC)=CC=C2OC HHZHOOXEMGLCJA-UHFFFAOYSA-N 0.000 claims description 2
- IRTOOLQOINXNHY-UHFFFAOYSA-N 1-(2-aminoethylamino)ethanol Chemical compound CC(O)NCCN IRTOOLQOINXNHY-UHFFFAOYSA-N 0.000 claims description 2
- NRKYWOKHZRQRJR-UHFFFAOYSA-N 2,2,2-trifluoroacetamide Chemical group NC(=O)C(F)(F)F NRKYWOKHZRQRJR-UHFFFAOYSA-N 0.000 claims description 2
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- 101100289061 Drosophila melanogaster lili gene Proteins 0.000 claims description 2
- 125000005251 aryl acyl group Chemical group 0.000 claims description 2
- 150000004678 hydrides Chemical class 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims description 2
- XURVRZSODRHRNK-UHFFFAOYSA-N o-quinodimethane Chemical compound C=C1C=CC=CC1=C XURVRZSODRHRNK-UHFFFAOYSA-N 0.000 claims description 2
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- 125000004001 thioalkyl group Chemical group 0.000 claims description 2
- 229910052727 yttrium Inorganic materials 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims 10
- 230000001580 bacterial effect Effects 0.000 claims 4
- 230000002538 fungal effect Effects 0.000 claims 4
- 230000003612 virological effect Effects 0.000 claims 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
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- 125000004965 chloroalkyl group Chemical group 0.000 claims 2
- DZNFUUFEJSIHLO-UHFFFAOYSA-N methyl 5,8-dioxo-3,4-dihydro-1h-isochromene-3-carboxylate Chemical compound O=C1C=CC(=O)C2=C1COC(C(=O)OC)C2 DZNFUUFEJSIHLO-UHFFFAOYSA-N 0.000 claims 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- HYIUCIGMIFBQDQ-UHFFFAOYSA-N 1-(1,5,8-trimethoxy-3,4-dihydro-1h-isochromen-3-yl)ethanone Chemical compound C1=CC(OC)=C2C(OC)OC(C(C)=O)CC2=C1OC HYIUCIGMIFBQDQ-UHFFFAOYSA-N 0.000 claims 1
- QSVQBBYVKDGFMS-UHFFFAOYSA-N 1-hydroxy-3-methyl-3,4-dihydro-1h-isochromene-5,8-dione Chemical compound O=C1C=CC(=O)C2=C1C(O)OC(C)C2 QSVQBBYVKDGFMS-UHFFFAOYSA-N 0.000 claims 1
- PQCPNRHRLIALAU-UHFFFAOYSA-N 2-cyano-2-methoxyacetic acid Chemical compound COC(C#N)C(O)=O PQCPNRHRLIALAU-UHFFFAOYSA-N 0.000 claims 1
- MSTDXOZUKAQDRL-UHFFFAOYSA-N 4-Chromanone Chemical compound C1=CC=C2C(=O)CCOC2=C1 MSTDXOZUKAQDRL-UHFFFAOYSA-N 0.000 claims 1
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- 101100226009 Arabidopsis thaliana ERCC1 gene Proteins 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
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- BGILBGROJLQASC-UHFFFAOYSA-N methyl 5,8-dioxo-3,4-dihydro-1h-isothiochromene-3-carboxylate Chemical compound O=C1C=CC(=O)C2=C1CSC(C(=O)OC)C2 BGILBGROJLQASC-UHFFFAOYSA-N 0.000 claims 1
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 317
- 239000000243 solution Substances 0.000 description 176
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P31/12—Antivirals
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/76—Benzo[c]pyrans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
- C07D327/06—Six-membered 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
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/72—Benzo[c]thiophenes; Hydrogenated benzo[c]thiophenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/24—Condensed ring systems having three or more rings
- C07H15/244—Anthraquinone radicals, e.g. sennosides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/24—Condensed ring systems having three or more rings
- C07H15/252—Naphthacene radicals, e.g. daunomycins, adriamycins
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
Landscapes
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- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Virology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Pyrane Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Forms Removed On Construction Sites Or Auxiliary Members Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US53610790A | 1990-06-11 | 1990-06-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS178691A3 true CS178691A3 (en) | 1992-01-15 |
Family
ID=24137175
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS911786A CS178691A3 (en) | 1990-06-11 | 1991-06-11 | Heterocyclic anthracyclinone and anthracycline analogs |
Country Status (18)
| Country | Link |
|---|---|
| EP (1) | EP0533744A1 (de) |
| JP (1) | JPH06504034A (de) |
| CN (1) | CN1058781A (de) |
| AP (1) | AP340A (de) |
| AU (1) | AU653348B2 (de) |
| CA (1) | CA2085120A1 (de) |
| CS (1) | CS178691A3 (de) |
| FI (1) | FI925611A7 (de) |
| HU (1) | HU9203720D0 (de) |
| IE (1) | IE911965A1 (de) |
| IL (1) | IL98460A0 (de) |
| MA (1) | MA22178A1 (de) |
| NZ (1) | NZ238490A (de) |
| PL (1) | PL297164A1 (de) |
| PT (1) | PT97931A (de) |
| WO (1) | WO1991019725A2 (de) |
| YU (1) | YU103391A (de) |
| ZA (1) | ZA914452B (de) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5736523A (en) * | 1992-11-09 | 1998-04-07 | Biochem Pharma Inc. | Antineoplastic heteronapthoquinones |
| EP0659190A1 (de) * | 1992-11-09 | 1995-06-28 | Biochem Pharma Inc | Antineoplastic heteronaphtochinone |
| US5606037A (en) * | 1992-11-09 | 1997-02-25 | Biochem Pharma Inc. | Processes antineoplastic heteronaphthoquinones |
| WO1995012588A1 (en) * | 1993-11-05 | 1995-05-11 | Biochem Pharma Inc. | Antineoplastic heteronaphthoquinones |
| IT1271689B (it) * | 1994-08-04 | 1997-06-04 | Menarini Farma Ind | 8-fluoro-antracicline, loro processi di preparazione e composizioni farmaceutiche che le contengono |
| JP2021534196A (ja) | 2018-08-23 | 2021-12-09 | シージェン インコーポレイテッド | 抗ｔｉｇｉｔ抗体 |
| CN111087377B (zh) * | 2020-03-19 | 2020-06-26 | 广东省微生物研究所（广东省微生物分析检测中心） | 苯并异色满醌类化合物及其制备方法和应用 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6030315B2 (ja) * | 1976-06-01 | 1985-07-16 | 三井東圧化学株式会社 | ４−ハロゲノメチルイソクマリン誘導体の製造法 |
| JPS52148088A (en) * | 1976-06-01 | 1977-12-08 | Richardson Merrell Inc | 111aminoalkylmorphansridinee 111ols |
| GB2067552B (en) * | 1980-01-16 | 1984-02-29 | Erba Farmitalia | Anthracyline derivatives |
| PH25651A (en) * | 1986-05-21 | 1991-08-21 | Duphar Int Res | New di, tetrahydroisoquinoline derivatives |
-
1991
- 1991-06-10 EP EP91910808A patent/EP0533744A1/de not_active Ceased
- 1991-06-10 PL PL29716491A patent/PL297164A1/xx unknown
- 1991-06-10 FI FI925611A patent/FI925611A7/fi unknown
- 1991-06-10 CA CA002085120A patent/CA2085120A1/en not_active Abandoned
- 1991-06-10 HU HU9203720A patent/HU9203720D0/hu unknown
- 1991-06-10 WO PCT/CA1991/000208 patent/WO1991019725A2/en not_active Ceased
- 1991-06-10 IE IE196591A patent/IE911965A1/en unknown
- 1991-06-10 AP APAP/P/1991/000278A patent/AP340A/en active
- 1991-06-10 AU AU80973/91A patent/AU653348B2/en not_active Ceased
- 1991-06-10 JP JP3510688A patent/JPH06504034A/ja active Pending
- 1991-06-11 IL IL98460A patent/IL98460A0/xx unknown
- 1991-06-11 CN CN91104005A patent/CN1058781A/zh active Pending
- 1991-06-11 MA MA22453A patent/MA22178A1/fr unknown
- 1991-06-11 PT PT97931A patent/PT97931A/pt not_active Application Discontinuation
- 1991-06-11 CS CS911786A patent/CS178691A3/cs unknown
- 1991-06-11 NZ NZ238490A patent/NZ238490A/en unknown
- 1991-06-11 ZA ZA914452A patent/ZA914452B/xx unknown
- 1991-06-11 YU YU103391A patent/YU103391A/sh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU653348B2 (en) | 1994-09-29 |
| CN1058781A (zh) | 1992-02-19 |
| WO1991019725A2 (en) | 1991-12-26 |
| HU9203720D0 (en) | 1993-03-29 |
| FI925611A0 (fi) | 1992-12-10 |
| PT97931A (pt) | 1992-03-31 |
| AP9100278A0 (en) | 1991-07-31 |
| AU8097391A (en) | 1992-01-07 |
| CA2085120A1 (en) | 1991-12-12 |
| JPH06504034A (ja) | 1994-05-12 |
| NZ238490A (en) | 1994-03-25 |
| ZA914452B (en) | 1992-06-24 |
| IL98460A0 (en) | 1992-07-15 |
| EP0533744A1 (de) | 1993-03-31 |
| FI925611L (fi) | 1992-12-10 |
| WO1991019725A3 (en) | 1992-04-30 |
| IE911965A1 (en) | 1991-12-18 |
| YU103391A (sh) | 1994-04-05 |
| MA22178A1 (fr) | 1991-12-31 |
| PL297164A1 (de) | 1992-10-05 |
| AP340A (en) | 1994-05-13 |
| FI925611A7 (fi) | 1992-12-10 |
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