CA1250833A - Process for preparing 4'-haloanthracycline glycosides - Google Patents
Process for preparing 4'-haloanthracycline glycosidesInfo
- Publication number
- CA1250833A CA1250833A CA000460796A CA460796A CA1250833A CA 1250833 A CA1250833 A CA 1250833A CA 000460796 A CA000460796 A CA 000460796A CA 460796 A CA460796 A CA 460796A CA 1250833 A CA1250833 A CA 1250833A
- Authority
- CA
- Canada
- Prior art keywords
- process according
- compound
- reaction
- group
- general formula
- 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.)
- Expired
Links
- 229930182470 glycoside Natural products 0.000 title claims abstract description 6
- 150000002338 glycosides Chemical class 0.000 title claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims abstract description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 8
- 229940045799 anthracyclines and related substance Drugs 0.000 claims abstract description 5
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 5
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 5
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 33
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 28
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical group [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 5
- 125000006242 amine protecting group Chemical group 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 239000000460 chlorine Chemical group 0.000 claims description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims description 2
- 238000005984 hydrogenation reaction Methods 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical group [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims 1
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical group [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 claims 1
- -1 trichloroethoxy-carbonyl group Chemical group 0.000 claims 1
- 230000000259 anti-tumor effect Effects 0.000 abstract description 4
- 229960000975 daunorubicin Drugs 0.000 abstract description 3
- 239000004280 Sodium formate Substances 0.000 abstract description 2
- 230000031709 bromination Effects 0.000 abstract description 2
- 238000005893 bromination reaction Methods 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 abstract description 2
- 235000019254 sodium formate Nutrition 0.000 abstract description 2
- 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 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 229960004679 doxorubicin Drugs 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 208000032839 leukemia Diseases 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 5
- 230000004083 survival effect Effects 0.000 description 5
- 206010028980 Neoplasm Diseases 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 230000003013 cytotoxicity Effects 0.000 description 3
- 231100000135 cytotoxicity Toxicity 0.000 description 3
- 230000034994 death Effects 0.000 description 3
- 231100000517 death Toxicity 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000002054 inoculum 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
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 230000001472 cytotoxic effect Effects 0.000 description 2
- 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
- 238000010511 deprotection reaction Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 2
- STQGQHZAVUOBTE-RPDDNNBZSA-N (7s,9s)-9-acetyl-7-[(2r,4s,5r,6s)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione Chemical class 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-RPDDNNBZSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 238000011735 C3H mouse Methods 0.000 description 1
- 208000000526 Experimental Leukemia Diseases 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 241001529936 Murinae Species 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000000434 field desorption mass spectrometry Methods 0.000 description 1
- 239000011737 fluorine 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
- 238000001727 in vivo Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB838321676A GB8321676D0 (en) | 1983-08-11 | 1983-08-11 | 4'-haloanthrocycline glycosides |
| GB8321676 | 1983-08-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1250833A true CA1250833A (en) | 1989-03-07 |
Family
ID=10547171
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000460796A Expired CA1250833A (en) | 1983-08-11 | 1984-08-10 | Process for preparing 4'-haloanthracycline glycosides |
Country Status (19)
| Country | Link |
|---|---|
| JP (1) | JPS6058997A (cs) |
| AT (1) | AT384226B (cs) |
| AU (1) | AU563396B2 (cs) |
| BE (1) | BE900336A (cs) |
| CA (1) | CA1250833A (cs) |
| CH (1) | CH660740A5 (cs) |
| CS (1) | CS270411B2 (cs) |
| DE (1) | DE3428945A1 (cs) |
| DK (1) | DK381884A (cs) |
| FI (1) | FI78109C (cs) |
| FR (1) | FR2554450B1 (cs) |
| GB (2) | GB8321676D0 (cs) |
| GR (1) | GR80046B (cs) |
| HU (1) | HU194266B (cs) |
| IT (1) | IT1209576B (cs) |
| NL (1) | NL8402477A (cs) |
| SE (1) | SE8404005L (cs) |
| SU (1) | SU1579465A3 (cs) |
| ZA (1) | ZA846147B (cs) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2159518A (en) * | 1984-06-08 | 1985-12-04 | Erba Farmitalia | New anthracyclines and process for manufacture |
| GB8414619D0 (en) * | 1984-06-08 | 1984-07-11 | Erba Farmitalia | Anthracyclines |
| DE3500017A1 (de) * | 1985-01-02 | 1986-07-10 | Farmitalia Carlo Erba S.p.A., Mailand/Milano | 4'-haloanthracyclinester |
| GB2218087B (en) * | 1988-04-22 | 1991-01-30 | Erba Carlo Spa | 4-demethoxy-4'-deoxy-4'iodo anthracycline glycosides |
| AU601857B2 (en) * | 1988-06-30 | 1990-09-20 | Pharmacia & Upjohn S.P.A. | A new antitumor agent obtained by microbial stereoselective reduction of 4'-deoxy-4'-iododoxorubicin |
| MA21995A1 (fr) * | 1989-11-13 | 1991-07-01 | Menarini Farma Ind | Nouvelles fluoronaphthacenediones,leurs derives glycozyles et leurs procedes de fabrication . |
| GB9418260D0 (en) * | 1994-09-09 | 1994-10-26 | Erba Carlo Spa | Anthracycline derivatives |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR892943A (fr) * | 1942-03-06 | 1944-05-24 | Ig Farbenindustrie Ag | Procédé pour épurer la dilactone gamma céto-pimélique |
| US4345070A (en) * | 1980-09-29 | 1982-08-17 | Farmitalia Carlo Erba S.P.A. | Process for the preparation of 4'-deoxy-daunorubicin and 4'-deoxy-doxorubicin |
| US4438105A (en) * | 1982-04-19 | 1984-03-20 | Farmaitalia Carlo Erba S.P.A | 4'-Iododerivatives of anthracycline glycosides |
-
1983
- 1983-08-11 GB GB838321676A patent/GB8321676D0/en active Pending
-
1984
- 1984-08-06 AT AT0253884A patent/AT384226B/de not_active IP Right Cessation
- 1984-08-06 IT IT8422232A patent/IT1209576B/it active
- 1984-08-06 DE DE3428945A patent/DE3428945A1/de not_active Withdrawn
- 1984-08-07 GR GR80046A patent/GR80046B/el unknown
- 1984-08-07 SU SU843781800A patent/SU1579465A3/ru active
- 1984-08-07 SE SE8404005A patent/SE8404005L/xx unknown
- 1984-08-07 AU AU31685/84A patent/AU563396B2/en not_active Ceased
- 1984-08-07 FR FR8412467A patent/FR2554450B1/fr not_active Expired
- 1984-08-08 FI FI843110A patent/FI78109C/fi not_active IP Right Cessation
- 1984-08-08 ZA ZA846147A patent/ZA846147B/xx unknown
- 1984-08-08 DK DK381884A patent/DK381884A/da not_active Application Discontinuation
- 1984-08-09 JP JP59165760A patent/JPS6058997A/ja active Pending
- 1984-08-09 GB GB08420237A patent/GB2144744B/en not_active Expired
- 1984-08-09 CS CS846052A patent/CS270411B2/cs unknown
- 1984-08-10 BE BE0/213475A patent/BE900336A/fr not_active IP Right Cessation
- 1984-08-10 HU HU843055A patent/HU194266B/hu not_active IP Right Cessation
- 1984-08-10 CA CA000460796A patent/CA1250833A/en not_active Expired
- 1984-08-10 CH CH3853/84A patent/CH660740A5/de not_active IP Right Cessation
- 1984-08-10 NL NL8402477A patent/NL8402477A/nl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB8420237D0 (en) | 1984-09-12 |
| GB2144744B (en) | 1986-12-03 |
| FR2554450A1 (fr) | 1985-05-10 |
| FI78109B (fi) | 1989-02-28 |
| GR80046B (en) | 1984-12-10 |
| CH660740A5 (de) | 1987-06-15 |
| FI843110A7 (fi) | 1985-02-12 |
| AU563396B2 (en) | 1987-07-09 |
| SU1579465A3 (ru) | 1990-07-15 |
| CS605284A2 (en) | 1989-11-14 |
| CS270411B2 (en) | 1990-06-13 |
| FR2554450B1 (fr) | 1987-01-30 |
| BE900336A (fr) | 1985-02-11 |
| AT384226B (de) | 1987-10-12 |
| JPS6058997A (ja) | 1985-04-05 |
| FI843110A0 (fi) | 1984-08-08 |
| NL8402477A (nl) | 1985-03-01 |
| ATA253884A (de) | 1987-03-15 |
| DK381884A (da) | 1985-02-12 |
| HU194266B (en) | 1988-01-28 |
| HUT35691A (en) | 1985-07-29 |
| SE8404005D0 (sv) | 1984-08-07 |
| FI78109C (fi) | 1989-06-12 |
| AU3168584A (en) | 1985-02-14 |
| DK381884D0 (da) | 1984-08-08 |
| GB8321676D0 (en) | 1983-09-14 |
| ZA846147B (en) | 1985-03-27 |
| GB2144744A (en) | 1985-03-13 |
| IT1209576B (it) | 1989-08-30 |
| DE3428945A1 (de) | 1985-02-28 |
| SE8404005L (sv) | 1985-02-12 |
| IT8422232A0 (it) | 1984-08-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |