JPS6036437A - アントラサイクリン誘導体およびその製法 - Google Patents
アントラサイクリン誘導体およびその製法Info
- Publication number
- JPS6036437A JPS6036437A JP59127644A JP12764484A JPS6036437A JP S6036437 A JPS6036437 A JP S6036437A JP 59127644 A JP59127644 A JP 59127644A JP 12764484 A JP12764484 A JP 12764484A JP S6036437 A JPS6036437 A JP S6036437A
- Authority
- JP
- Japan
- Prior art keywords
- rod
- roa
- physiologically acceptable
- acid addition
- addition salts
- Prior art date
- 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
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 229940045799 anthracyclines and related substance Drugs 0.000 title description 14
- 239000000203 mixture Substances 0.000 claims description 64
- 150000001875 compounds Chemical class 0.000 claims description 53
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 51
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 45
- 239000012071 phase Substances 0.000 claims description 28
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 27
- 239000000243 solution Substances 0.000 claims description 25
- 238000002955 isolation Methods 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- 238000004587 chromatography analysis Methods 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 11
- 235000015097 nutrients Nutrition 0.000 claims description 11
- 239000000741 silica gel Substances 0.000 claims description 11
- 229910002027 silica gel Inorganic materials 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 10
- 239000008346 aqueous phase Substances 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 238000000605 extraction Methods 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 244000005700 microbiome Species 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 238000000638 solvent extraction Methods 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 238000004185 countercurrent chromatography Methods 0.000 claims description 5
- 229930182470 glycoside Natural products 0.000 claims description 4
- 238000004809 thin layer chromatography Methods 0.000 claims description 3
- 239000011573 trace mineral Substances 0.000 claims description 3
- 235000013619 trace mineral Nutrition 0.000 claims description 3
- ATPYMFXOZQEWIG-LFRDXLMFSA-N (2s,5r,6s)-5,6-dihydroxy-2-methyloxan-3-one Chemical group C[C@@H]1O[C@H](O)[C@H](O)CC1=O ATPYMFXOZQEWIG-LFRDXLMFSA-N 0.000 claims description 2
- 239000008351 acetate buffer Substances 0.000 claims description 2
- 239000003463 adsorbent Substances 0.000 claims description 2
- 239000002024 ethyl acetate extract Substances 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims 3
- 239000012059 conventional drug carrier Substances 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000004810 partition chromatography Methods 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 84
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 239000000047 product Substances 0.000 description 22
- 239000002609 medium Substances 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 238000010586 diagram Methods 0.000 description 18
- 229920001817 Agar Polymers 0.000 description 17
- 239000008272 agar Substances 0.000 description 17
- 238000012360 testing method Methods 0.000 description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 210000004027 cell Anatomy 0.000 description 15
- 241000187747 Streptomyces Species 0.000 description 12
- 239000012153 distilled water Substances 0.000 description 12
- 238000000862 absorption spectrum Methods 0.000 description 11
- 239000010410 layer Substances 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- 239000003242 anti bacterial agent Substances 0.000 description 9
- 229940088710 antibiotic agent Drugs 0.000 description 9
- 239000000284 extract Substances 0.000 description 9
- 230000012010 growth Effects 0.000 description 9
- 239000002689 soil Substances 0.000 description 9
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 8
- 239000008103 glucose Substances 0.000 description 8
- 238000000855 fermentation Methods 0.000 description 7
- 230000004151 fermentation Effects 0.000 description 7
- 239000002054 inoculum Substances 0.000 description 7
- 238000012746 preparative thin layer chromatography Methods 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 229920002472 Starch Polymers 0.000 description 6
- 229910000831 Steel Inorganic materials 0.000 description 6
- 229940041514 candida albicans extract Drugs 0.000 description 6
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 239000008107 starch Substances 0.000 description 6
- 239000010959 steel Substances 0.000 description 6
- 239000012138 yeast extract Substances 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 230000003115 biocidal effect Effects 0.000 description 5
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 5
- 238000010828 elution Methods 0.000 description 5
- 210000002196 fr. b Anatomy 0.000 description 5
- 239000001963 growth medium Substances 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 235000019698 starch Nutrition 0.000 description 5
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 4
- 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 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 description 4
- DUYAAUVXQSMXQP-UHFFFAOYSA-N ethanethioic S-acid Chemical compound CC(S)=O DUYAAUVXQSMXQP-UHFFFAOYSA-N 0.000 description 4
- 210000003918 fraction a Anatomy 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000013587 production medium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 239000005018 casein Substances 0.000 description 3
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 3
- 235000021240 caseins Nutrition 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 238000012258 culturing Methods 0.000 description 3
- 235000021186 dishes Nutrition 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 235000013312 flour Nutrition 0.000 description 3
- 150000002338 glycosides Chemical class 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- 230000006651 lactation Effects 0.000 description 3
- -1 lipose Chemical compound 0.000 description 3
- 238000004811 liquid chromatography Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000003643 water by type Substances 0.000 description 3
- STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 description 2
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 2
- PITHJRRCEANNKJ-UHFFFAOYSA-N Aclacinomycin A Natural products C12=C(O)C=3C(=O)C4=CC=CC=C4C(=O)C=3C=C2C(C(=O)OC)C(CC)(O)CC1OC(OC1C)CC(N(C)C)C1OC(OC1C)CC(O)C1OC1CCC(=O)C(C)O1 PITHJRRCEANNKJ-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
- 239000005695 Ammonium acetate Substances 0.000 description 2
- 244000144730 Amygdalus persica Species 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- DWRXFEITVBNRMK-UHFFFAOYSA-N Beta-D-1-Arabinofuranosylthymine Natural products O=C1NC(=O)C(C)=CN1C1C(O)C(O)C(CO)O1 DWRXFEITVBNRMK-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 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 2
- WEAHRLBPCANXCN-UHFFFAOYSA-N Daunomycin Natural products CCC1(O)CC(OC2CC(N)C(O)C(C)O2)c3cc4C(=O)c5c(OC)cccc5C(=O)c4c(O)c3C1 WEAHRLBPCANXCN-UHFFFAOYSA-N 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
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- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
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- 230000002378 acidificating effect Effects 0.000 description 2
- USZYSDMBJDPRIF-SVEJIMAYSA-N aclacinomycin A Chemical compound O([C@H]1[C@@H](O)C[C@@H](O[C@H]1C)O[C@H]1[C@H](C[C@@H](O[C@H]1C)O[C@H]1C[C@]([C@@H](C2=CC=3C(=O)C4=CC=CC(O)=C4C(=O)C=3C(O)=C21)C(=O)OC)(O)CC)N(C)C)[C@H]1CCC(=O)[C@H](C)O1 USZYSDMBJDPRIF-SVEJIMAYSA-N 0.000 description 2
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- STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin 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(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
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- AKRQHOWXVSDJEF-UHFFFAOYSA-N heptane-1-sulfonic acid Chemical compound CCCCCCCS(O)(=O)=O AKRQHOWXVSDJEF-UHFFFAOYSA-N 0.000 description 2
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- 229910000357 manganese(II) sulfate Inorganic materials 0.000 description 2
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- 239000000052 vinegar Substances 0.000 description 2
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- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 2
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- 239000011686 zinc sulphate Substances 0.000 description 2
- 235000009529 zinc sulphate Nutrition 0.000 description 2
- RWCVSDKDFSVZNF-KRYGIPSASA-N (1R,2R,4S)-2-ethyl-2,4,5,7,10-pentahydroxy-6,11-dioxo-3,4-dihydro-1H-tetracene-1-carboxylic acid methyl ester Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(O)=C1[C@@H](O)C[C@@](CC)(O)[C@H](C(=O)OC)C1=C2 RWCVSDKDFSVZNF-KRYGIPSASA-N 0.000 description 1
- UQZSVIGPZAULMV-DKWTVANSSA-N (2s)-2,4-diamino-4-oxobutanoic acid;propane-1,2,3-triol Chemical compound OCC(O)CO.OC(=O)[C@@H](N)CC(N)=O UQZSVIGPZAULMV-DKWTVANSSA-N 0.000 description 1
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- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P1/00—Preparation of compounds or compositions, not provided for in groups C12P3/00 - C12P39/00, by using microorganisms or enzymes
- C12P1/04—Preparation of compounds or compositions, not provided for in groups C12P3/00 - C12P39/00, by using microorganisms or enzymes by using bacteria
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- 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
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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
- A61P35/00—Antineoplastic agents
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/44—Preparation of O-glycosides, e.g. glucosides
- C12P19/56—Preparation of O-glycosides, e.g. glucosides having an oxygen atom of the saccharide radical directly bound to a condensed ring system having three or more carbocyclic rings, e.g. daunomycin, adriamycin
Landscapes
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- Molecular Biology (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Mycology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3323025A DE3323025A1 (de) | 1983-06-25 | 1983-06-25 | Anthracyclin-derivate, ein mikrobiologisches verfahren zu ihrer herstellung und ihre verwendung als cytostatika |
| DE3323025.0 | 1983-06-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6036437A true JPS6036437A (ja) | 1985-02-25 |
Family
ID=6202458
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59127644A Pending JPS6036437A (ja) | 1983-06-25 | 1984-06-22 | アントラサイクリン誘導体およびその製法 |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4713371A (enExample) |
| EP (1) | EP0131181B1 (enExample) |
| JP (1) | JPS6036437A (enExample) |
| KR (1) | KR850000529A (enExample) |
| AT (1) | ATE50776T1 (enExample) |
| AU (1) | AU578615B2 (enExample) |
| CA (1) | CA1244364A (enExample) |
| DE (2) | DE3323025A1 (enExample) |
| DK (1) | DK306584A (enExample) |
| ES (1) | ES533631A0 (enExample) |
| FI (1) | FI80071C (enExample) |
| GR (1) | GR81630B (enExample) |
| HU (1) | HU195979B (enExample) |
| IL (1) | IL72214A0 (enExample) |
| MX (1) | MX7303E (enExample) |
| NO (1) | NO160011C (enExample) |
| NZ (1) | NZ208622A (enExample) |
| PH (1) | PH22276A (enExample) |
| PT (1) | PT78784B (enExample) |
| ZA (1) | ZA844742B (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3325957A1 (de) * | 1983-07-19 | 1985-02-07 | Hoechst Ag, 6230 Frankfurt | Anthracyclin-derivate, ein verfahren zu ihrer herstellung und ihre verwendung als cytostatika |
| JPS6117597A (ja) * | 1984-07-03 | 1986-01-25 | Microbial Chem Res Found | アントラサイクリン化合物 |
| DE3524117A1 (de) * | 1985-07-05 | 1987-02-05 | Hoechst Ag | Neue anthracyclin-tetrasaccharide, ein verfahren zu ihrer herstellung und ihre verwendung als cytostatik |
| DE3706175A1 (de) * | 1987-02-26 | 1988-09-08 | Behringwerke Ag | Verwendung von lipophilen anthracyclinen zur behandlung "sekundaer" anthracyclin-resistenter tumoren, mittel enthaltend ein lipophiles anthracyclin und verfahren zu seiner herstellung |
| DE3712350A1 (de) * | 1987-04-11 | 1988-10-20 | Behringwerke Ag | Semisynthetische rhodomycine, verfahren zu ihrer herstellung und ihre verwendung als zytostatika |
| US4918172A (en) * | 1987-10-06 | 1990-04-17 | Sanraku Incorporated | Anthracycline antibiotics |
| DE3842836A1 (de) * | 1988-12-20 | 1990-06-21 | Behringwerke Ag | Rhodomycine mit einer modifizierten kohlenhydrat-einheit |
| DE3920062A1 (de) * | 1989-06-20 | 1991-01-10 | Hoechst Ag | Neue anthracyclin-derivate, ein verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| FI93860C (fi) * | 1991-03-25 | 1995-06-12 | Leiras Oy | Menetelmä antibioottien tuottamiseksi, siinä käyttökelpoisia DNA-jaksoja, yhdistelmä-DNA-konstruktioita ja näitä sisältäviä mikrobikantoja |
| DE10029433A1 (de) * | 2000-06-15 | 2001-12-20 | Bioleads Gmbh | Rhodomycinon-Derivate |
| NZ575452A (en) | 2002-05-24 | 2010-03-26 | Angiotech Int Ag | Compositions and methods for coating medical implants such as vascular grafts, catheters, pacemakers etc |
| US8313760B2 (en) | 2002-05-24 | 2012-11-20 | Angiotech International Ag | Compositions and methods for coating medical implants |
| TW200510719A (en) * | 2003-08-06 | 2005-03-16 | Pharmacia Italia Spa | Method for detecting contaminants in pharmaceutical products |
| WO2005051444A2 (en) * | 2003-11-20 | 2005-06-09 | Angiotech International Ag | Soft tissue implants and anti-scarring agents |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55120786A (en) * | 1979-03-14 | 1980-09-17 | Sanraku Inc | Variant capable of producing anthracycline glycoside |
| JPS5615299A (en) * | 1979-07-13 | 1981-02-14 | Sanraku Inc | Rhodomycin group antibiotic and its preparation |
| JPS5796000A (en) * | 1980-10-16 | 1982-06-15 | Hoffmann La Roche | Novel anthracyclines |
| JPS57114547A (en) * | 1981-01-07 | 1982-07-16 | Sanraku Inc | Anthracycline antibiotic substance and its preparation |
| JPS5826895A (ja) * | 1981-08-11 | 1983-02-17 | Sanraku Inc | ２‐ヒドロキシアクラシノマイシンｂ |
| JPS5874694A (ja) * | 1981-10-29 | 1983-05-06 | Sanraku Inc | アントラサイクリン誘導体 |
| JPS5982395A (ja) * | 1982-11-02 | 1984-05-12 | Microbial Chem Res Found | アントラサイクリン化合物、その製造法およびその用途 |
| JPS59231023A (ja) * | 1983-11-11 | 1984-12-25 | Ajinomoto Co Inc | 抗腫瘍剤 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5323961A (en) * | 1976-08-16 | 1978-03-06 | Microbial Chem Res Found | Antitumors |
| JPS57176995A (en) * | 1981-04-23 | 1982-10-30 | Sanraku Inc | Novel anthracyclinone glycoside and its preparation |
-
1983
- 1983-06-25 DE DE3323025A patent/DE3323025A1/de not_active Withdrawn
-
1984
- 1984-06-18 HU HU842338A patent/HU195979B/hu not_active IP Right Cessation
- 1984-06-19 EP EP84106995A patent/EP0131181B1/de not_active Expired - Lifetime
- 1984-06-19 DE DE8484106995T patent/DE3481515D1/de not_active Expired - Fee Related
- 1984-06-19 AT AT84106995T patent/ATE50776T1/de active
- 1984-06-21 FI FI842523A patent/FI80071C/fi not_active IP Right Cessation
- 1984-06-22 AU AU29812/84A patent/AU578615B2/en not_active Ceased
- 1984-06-22 ES ES533631A patent/ES533631A0/es active Granted
- 1984-06-22 NO NO842546A patent/NO160011C/no unknown
- 1984-06-22 JP JP59127644A patent/JPS6036437A/ja active Pending
- 1984-06-22 DK DK306584A patent/DK306584A/da not_active Application Discontinuation
- 1984-06-22 MX MX8411189U patent/MX7303E/es unknown
- 1984-06-22 ZA ZA844742A patent/ZA844742B/xx unknown
- 1984-06-22 GR GR75085A patent/GR81630B/el unknown
- 1984-06-22 CA CA000457301A patent/CA1244364A/en not_active Expired
- 1984-06-22 NZ NZ208622A patent/NZ208622A/en unknown
- 1984-06-25 PT PT78784A patent/PT78784B/pt not_active IP Right Cessation
- 1984-06-25 IL IL72214A patent/IL72214A0/xx unknown
- 1984-06-25 KR KR1019840003590A patent/KR850000529A/ko not_active Ceased
- 1984-06-25 PH PH30879A patent/PH22276A/en unknown
-
1986
- 1986-02-03 US US06/824,939 patent/US4713371A/en not_active Expired - Fee Related
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55120786A (en) * | 1979-03-14 | 1980-09-17 | Sanraku Inc | Variant capable of producing anthracycline glycoside |
| JPS5615299A (en) * | 1979-07-13 | 1981-02-14 | Sanraku Inc | Rhodomycin group antibiotic and its preparation |
| JPS5796000A (en) * | 1980-10-16 | 1982-06-15 | Hoffmann La Roche | Novel anthracyclines |
| JPS57114547A (en) * | 1981-01-07 | 1982-07-16 | Sanraku Inc | Anthracycline antibiotic substance and its preparation |
| JPS5826895A (ja) * | 1981-08-11 | 1983-02-17 | Sanraku Inc | ２‐ヒドロキシアクラシノマイシンｂ |
| JPS5874694A (ja) * | 1981-10-29 | 1983-05-06 | Sanraku Inc | アントラサイクリン誘導体 |
| JPS5982395A (ja) * | 1982-11-02 | 1984-05-12 | Microbial Chem Res Found | アントラサイクリン化合物、その製造法およびその用途 |
| JPS59231023A (ja) * | 1983-11-11 | 1984-12-25 | Ajinomoto Co Inc | 抗腫瘍剤 |
Also Published As
| Publication number | Publication date |
|---|---|
| HUT44803A (en) | 1988-04-28 |
| KR850000529A (ko) | 1985-02-27 |
| US4713371A (en) | 1987-12-15 |
| FI842523A0 (fi) | 1984-06-21 |
| DE3323025A1 (de) | 1985-01-10 |
| GR81630B (enExample) | 1984-12-11 |
| AU578615B2 (en) | 1988-11-03 |
| EP0131181A3 (en) | 1985-05-22 |
| DK306584D0 (da) | 1984-06-22 |
| ES8601230A1 (es) | 1985-10-16 |
| ES533631A0 (es) | 1985-10-16 |
| IL72214A0 (en) | 1984-10-31 |
| NZ208622A (en) | 1988-02-29 |
| ZA844742B (en) | 1985-02-27 |
| PT78784A (de) | 1984-07-01 |
| NO160011C (no) | 1989-03-01 |
| FI80071C (fi) | 1990-04-10 |
| HU195979B (en) | 1988-08-29 |
| DK306584A (da) | 1984-12-26 |
| EP0131181B1 (de) | 1990-03-07 |
| FI842523A7 (fi) | 1984-12-26 |
| ATE50776T1 (de) | 1990-03-15 |
| FI80071B (fi) | 1989-12-29 |
| AU2981284A (en) | 1985-01-03 |
| NO160011B (no) | 1988-11-21 |
| NO842546L (no) | 1984-12-27 |
| PT78784B (de) | 1986-07-22 |
| EP0131181A2 (de) | 1985-01-16 |
| CA1244364A (en) | 1988-11-08 |
| DE3481515D1 (de) | 1990-04-12 |
| MX7303E (es) | 1988-04-29 |
| PH22276A (en) | 1988-07-14 |
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