JPS61106590A - アントラサイクリングリコシド - Google Patents

アントラサイクリングリコシド

Info

Publication number: JPS61106590A
Authority: JP; Japan
Prior art keywords: solution; hydroxy; demethoxy; compound; trifluoroacetyl
Prior art date: 1984-08-24
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Pending

Application number

JP60183147A

Other languages

English (en)

Japanese (ja)

Inventor

フランセスコ・アンゲルツシ

ギオヴアンナ・バルチエリ

マウロ・ギグリ

セルギオ・ペンコ

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Pfizer Italia SRL

Original Assignee

Farmitalia Carlo Erba SRL

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1984-08-24

Filing date

1985-08-22

Publication date

1986-05-24

1985-08-22 Application filed by Farmitalia Carlo Erba SRL filed Critical Farmitalia Carlo Erba SRL

1986-05-24 Publication of JPS61106590A publication Critical patent/JPS61106590A/ja

Status Pending legal-status Critical Current

Links

150000002338 glycosides Chemical class 0.000 title claims description 10
229930182470 glycoside Natural products 0.000 title claims description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 12
238000000034 method Methods 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 6
229940045799 anthracyclines and related substance Drugs 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
CZKMPDNXOGQMFW-UHFFFAOYSA-N chloro(triethyl)germane Chemical compound CC[Ge](Cl)(CC)CC CZKMPDNXOGQMFW-UHFFFAOYSA-N 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
238000005904 alkaline hydrolysis reaction Methods 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
238000006140 methanolysis reaction Methods 0.000 claims description 2
239000000741 silica gel Substances 0.000 claims description 2
229910002027 silica gel Inorganic materials 0.000 claims description 2
239000000126 substance Substances 0.000 claims description 2
SDWZXVTWORCAMD-MVGXARHUSA-N 2-[[3-hydroxy-2-methyl-6-[[(1s,3s)-3,5,12-trihydroxy-3-(2-hydroxyacetyl)-10-methoxy-6,11-dioxo-2,4-dihydro-1h-tetracen-1-yl]oxy]oxan-4-yl]amino]acetonitrile Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)C1CC(NCC#N)C(O)C(C)O1 SDWZXVTWORCAMD-MVGXARHUSA-N 0.000 claims 1
239000000243 solution Substances 0.000 description 56
150000001875 compounds Chemical class 0.000 description 41
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
239000000203 mixture Substances 0.000 description 17
239000002904 solvent Substances 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000000047 product Substances 0.000 description 10
229920006395 saturated elastomer Polymers 0.000 description 10
235000017557 sodium bicarbonate Nutrition 0.000 description 10
229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
150000002148 esters Chemical class 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
239000011780 sodium chloride Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
238000005481 NMR spectroscopy Methods 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
238000001704 evaporation Methods 0.000 description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
239000012044 organic layer Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
238000010586 diagram Methods 0.000 description 4
210000000936 intestine Anatomy 0.000 description 4
239000010410 layer Substances 0.000 description 4
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
238000005160 1H NMR spectroscopy Methods 0.000 description 3
BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
IXFBIAAVYHNLOO-UHFFFAOYSA-N [Li]C=1C=C(C2=CC=CC(=C2C1OC)OC)OC Chemical compound [Li]C=1C=C(C2=CC=CC(=C2C1OC)OC)OC IXFBIAAVYHNLOO-UHFFFAOYSA-N 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
238000005859 coupling reaction Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000012071 phase Substances 0.000 description 3
ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 3
239000007787 solid Substances 0.000 description 3
101100136092 Drosophila melanogaster peng gene Proteins 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 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
241000600169 Maro Species 0.000 description 2
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
150000004056 anthraquinones Chemical class 0.000 description 2
125000001743 benzylic group Chemical group 0.000 description 2
229910000085 borane Inorganic materials 0.000 description 2
230000031709 bromination Effects 0.000 description 2
238000005893 bromination reaction Methods 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
239000013058 crude material Substances 0.000 description 2
125000000422 delta-lactone group Chemical group 0.000 description 2
239000003480 eluent Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
150000002596 lactones Chemical class 0.000 description 2
229910003002 lithium salt Inorganic materials 0.000 description 2
159000000002 lithium salts Chemical class 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000002243 precursor Substances 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
239000000725 suspension Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
QOYHOHVBDOFRJP-UHFFFAOYSA-N 2,3-dichlorobenzenecarboperoxoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1Cl QOYHOHVBDOFRJP-UHFFFAOYSA-N 0.000 description 1
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical compound O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 description 1
VTEFKKQAHLQVHI-UHFFFAOYSA-N 2-bromo-1,4,8-trimethoxynaphthalene Chemical compound C1=C(Br)C(OC)=C2C(OC)=CC=CC2=C1OC VTEFKKQAHLQVHI-UHFFFAOYSA-N 0.000 description 1
OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 1
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
229940126062 Compound A Drugs 0.000 description 1
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
235000010469 Glycine max Nutrition 0.000 description 1
244000068988 Glycine max Species 0.000 description 1
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
239000004280 Sodium formate Substances 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
239000003513 alkali Substances 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
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 1
230000001093 anti-cancer Effects 0.000 description 1
239000012267 brine Substances 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
229940126214 compound 3 Drugs 0.000 description 1
239000004020 conductor Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
150000001935 cyclohexenes Chemical class 0.000 description 1
229960000975 daunorubicin Drugs 0.000 description 1
238000010828 elution Methods 0.000 description 1
238000006735 epoxidation reaction Methods 0.000 description 1
PDGUSEMLUHMLGJ-UHFFFAOYSA-N ethanamine methylsulfinylmethane Chemical compound CS(=O)C.CCN PDGUSEMLUHMLGJ-UHFFFAOYSA-N 0.000 description 1
238000001914 filtration Methods 0.000 description 1
125000000457 gamma-lactone group Chemical group 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
239000000499 gel Substances 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000017693 oxidative demethylation Effects 0.000 description 1
238000007067 oxidative demethylation reaction Methods 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
-1 p-nitrophenyl ester Chemical class 0.000 description 1
230000010412 perfusion Effects 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
150000003333 secondary alcohols Chemical class 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
CBXWGGFGZDVPNV-UHFFFAOYSA-N so4-so4 Chemical class OS(O)(=O)=O.OS(O)(=O)=O CBXWGGFGZDVPNV-UHFFFAOYSA-N 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
235000019254 sodium formate Nutrition 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
238000003797 solvolysis reaction Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1
150000008135 α-glycosides Chemical class 0.000 description 1

Classifications

- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)

JP60183147A 1984-08-24 1985-08-22 アントラサイクリングリコシド Pending JPS61106590A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB848421491A GB8421491D0 (en)	1984-08-24	1984-08-24	Anthracycline glycosides
GB8421491		1984-08-24

Publications (1)

Publication Number	Publication Date
JPS61106590A true JPS61106590A (ja)	1986-05-24

Family

ID=10565768

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP60183147A Pending JPS61106590A (ja)	1984-08-24	1985-08-22	アントラサイクリングリコシド

Country Status (8)

Country	Link
JP (1)	JPS61106590A (fr)
BE (1)	BE903095A (fr)
DE (1)	DE3529794A1 (fr)
FR (1)	FR2569405A1 (fr)
GB (2)	GB8421491D0 (fr)
IT (1)	IT1214492B (fr)
NL (1)	NL8502303A (fr)
SE (1)	SE8503877L (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9418260D0 (en) *	1994-09-09	1994-10-26	Erba Carlo Spa	Anthracycline derivatives

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5543012A (en) *	1978-09-20	1980-03-26	Sanraku Inc	Novel anthracycline derivatine and its preparation
IT1210476B (it) *	1981-05-28	1989-09-14	Erba Farmitalia	Antracicline.
FR2551057B1 (fr) *	1983-08-30	1986-07-18	Hoechst Lab	Nouveaux aglycones utiles pour la preparation des antibiotiques et des antitumoraux de la serie des anthracyclines et leurs procedes de preparation

1984
- 1984-08-24 GB GB848421491A patent/GB8421491D0/en active Pending
1985
- 1985-08-19 SE SE8503877A patent/SE8503877L/xx not_active Application Discontinuation
- 1985-08-20 DE DE19853529794 patent/DE3529794A1/de not_active Withdrawn
- 1985-08-20 GB GB08520835A patent/GB2164335A/en not_active Withdrawn
- 1985-08-20 FR FR8512520A patent/FR2569405A1/fr not_active Withdrawn
- 1985-08-21 BE BE0/215487A patent/BE903095A/fr unknown
- 1985-08-21 NL NL8502303A patent/NL8502303A/nl not_active Application Discontinuation
- 1985-08-22 JP JP60183147A patent/JPS61106590A/ja active Pending
- 1985-08-22 IT IT8521965A patent/IT1214492B/it active

Also Published As

Publication number	Publication date
SE8503877L (sv)	1986-02-25
DE3529794A1 (de)	1986-03-06
GB8520835D0 (en)	1985-09-25
GB8421491D0 (en)	1984-09-26
BE903095A (fr)	1985-12-16
FR2569405A1 (fr)	1986-02-28
IT8521965A0 (it)	1985-08-22
NL8502303A (nl)	1986-03-17
GB2164335A (en)	1986-03-19
SE8503877D0 (sv)	1985-08-19
IT1214492B (it)	1990-01-18

Publication	Publication Date	Title
US4012448A (en)	1977-03-15	Synthesis of adriamycin and 7,9-epiadriamycin
EP0288268B1 (fr)	1992-12-09	4-Déméthoxy-4-aminoanthracyclines
US4215062A (en)	1980-07-29	Anthracycline synthesis
Florent et al.	1987	Anthracyclinones. 2. Isosaccharinic acid as chiral template for the synthesis of (+)-4-demethoxy-9-deacetyl-9-hydroxymethyldaunomycinone and (-)-4-deoxy-. gamma.-rhodomycinone
US4465671A (en)	1984-08-14	Anthracycline glycosides use and compositions containing same
Suzuki et al.	1978	Total synthesis of anthracyclinones via intramolecular base-catalyzed cyclizations
TAMURA et al.	1987	An efficient, regiospecific synthesis of 4-demethoxydaunomycinone and daunomycinone
Findlay et al.	1983	On the structure, chemistry, and 13C nuclear magnetic resonance of ravidomycin
Ichihara et al.	1982	Synthesis of (±)-epoxydon and related natural compounds
JPS61106590A (ja)	1986-05-24	アントラサイクリングリコシド
Tsunakawa et al.	1980	Bu-2313, a new antibiotic complex active against anaerobes II. Structure determination of Bu-2313 A and B
US4939282A (en)	1990-07-03	The process for preparing 6-deoxynthracyclines
US4563444A (en)	1986-01-07	Anthracycline glycosides, use and compositions containing same
CA1179331A (fr)	1984-12-11	Synthese regiospecifique de composes a base d'anthracyclinone comme daunomycinone
Penco et al.	1984	Regiospecific total synthesis of 6-deoxyanthracyclines
JPH0778073B2 (ja)	1995-08-23	ニトロアントラサイクリン、その製造方法およびその使用
JPH0272186A (ja)	1990-03-12	１０―ノルアントラサイクリン
Olivier et al.	1980	Two new germacranolides from Melampodium leucanthum and their reductive and oxidative rearrangements
US5138042A (en)	1992-08-11	6-deoxyanthracyclines
JPS5939855A (ja)	1984-03-05	９−（３，４−ジメトキシ−２−ヒドロキシ−６−メチルベンゾイル）ノナノエ−トの製造法
KAMETANI et al.	1978	Studies on the Syntheses of Tetracycline Derivatives. III. Synthetic Approach to Adriamycin-Synthesis of the Linear Tetracyclic Skeleton having the Same BC Ring System with Adriamycin
KIMURA et al.	1987	Spirolactones of xanthene. IV. New method of xanthone synthesis by oxidation of novel spirolactones of dibenzo [c, h] xanthene and xanthenes
Fraga et al.	1986	The partial synthesis of 6-epi-gibberellin A 13 and 6-epi-gibberellin A 25 derivatives
GB2191479A (en)	1987-12-16	Antitumor anthracycline glycosides
JPH0351697B2 (fr)	1991-08-07