RU2073681C1 - Антрациклиновый гликозид и способы его получения - Google Patents
Антрациклиновый гликозид и способы его получения Download PDFInfo
- Publication number
- RU2073681C1 RU2073681C1 SU905001277A SU5001277A RU2073681C1 RU 2073681 C1 RU2073681 C1 RU 2073681C1 SU 905001277 A SU905001277 A SU 905001277A SU 5001277 A SU5001277 A SU 5001277A RU 2073681 C1 RU2073681 C1 RU 2073681C1
- Authority
- RU
- Russia
- Prior art keywords
- amino
- deoxy
- group
- epi
- hydrochloride
- Prior art date
Links
- 229930182470 glycoside Natural products 0.000 title claims abstract description 46
- 150000002338 glycosides Chemical class 0.000 title claims abstract description 44
- 229940045799 anthracyclines and related substance Drugs 0.000 title claims abstract description 19
- 238000000034 method Methods 0.000 title claims description 35
- 230000015572 biosynthetic process Effects 0.000 title description 3
- 238000003786 synthesis reaction Methods 0.000 title description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 25
- 125000003277 amino group Chemical group 0.000 claims abstract description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- 239000001257 hydrogen Substances 0.000 claims abstract description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 9
- -1 HYDROXY group Chemical group 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 49
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 47
- 150000003839 salts Chemical class 0.000 claims description 25
- 229960004679 doxorubicin Drugs 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 18
- 229960000975 daunorubicin Drugs 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 125000006239 protecting group Chemical group 0.000 claims description 10
- DKVBOUDTNWVDEP-NJCHZNEYSA-N teicoplanin aglycone Chemical compound N([C@H](C(N[C@@H](C1=CC(O)=CC(O)=C1C=1C(O)=CC=C2C=1)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)OC=1C=C3C=C(C=1O)OC1=CC=C(C=C1Cl)C[C@H](C(=O)N1)NC([C@H](N)C=4C=C(O5)C(O)=CC=4)=O)C(=O)[C@@H]2NC(=O)[C@@H]3NC(=O)[C@@H]1C1=CC5=CC(O)=C1 DKVBOUDTNWVDEP-NJCHZNEYSA-N 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 230000031709 bromination Effects 0.000 claims description 2
- 238000005893 bromination reaction Methods 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 6
- 150000004820 halides Chemical class 0.000 claims 2
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract description 2
- 239000002246 antineoplastic agent Substances 0.000 abstract description 2
- 229910052731 fluorine Inorganic materials 0.000 abstract description 2
- 239000011737 fluorine Chemical group 0.000 abstract description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 144
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 99
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 65
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 36
- 239000002904 solvent Substances 0.000 description 30
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 29
- 238000002360 preparation method Methods 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 238000001819 mass spectrum Methods 0.000 description 17
- 239000000203 mixture Substances 0.000 description 17
- 238000005160 1H NMR spectroscopy Methods 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 13
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 13
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 10
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- 238000000434 field desorption mass spectrometry Methods 0.000 description 8
- 239000012458 free base Substances 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 7
- CZKMPDNXOGQMFW-UHFFFAOYSA-N chloro(triethyl)germane Chemical compound CC[Ge](Cl)(CC)CC CZKMPDNXOGQMFW-UHFFFAOYSA-N 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- 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 5
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 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
- 239000002808 molecular sieve Substances 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 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 4
- 239000011541 reaction mixture Substances 0.000 description 4
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- XYDJGVROLWFENK-YBTHPKLGSA-N (7s,9s)-9-acetyl-4,6,7,9,11-pentahydroxy-8,10-dihydro-7h-tetracene-5,12-dione Chemical compound O=C1C2=C(O)C=CC=C2C(=O)C2=C1C(O)=C1[C@@H](O)C[C@@](C(=O)C)(O)CC1=C2O XYDJGVROLWFENK-YBTHPKLGSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 229960003109 daunorubicin hydrochloride Drugs 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 150000003840 hydrochlorides Chemical class 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000004280 Sodium formate Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229940126575 aminoglycoside Drugs 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 201000010897 colon adenocarcinoma Diseases 0.000 description 2
- 208000029742 colonic neoplasm Diseases 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 229960002918 doxorubicin hydrochloride Drugs 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 150000002828 nitro derivatives Chemical class 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 235000011056 potassium acetate Nutrition 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 2
- 235000019254 sodium formate Nutrition 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 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 description 1
- 0 CC(C1)C(*)CCC1OC(CC(Cc1c2*)(C(*)=O)O)c1c(*)c(C(c1c3cccc1*)=O)c2C3=O Chemical compound CC(C1)C(*)CCC1OC(CC(Cc1c2*)(C(*)=O)O)c1c(*)c(C(c1c3cccc1*)=O)c2C3=O 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 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
- 241000124008 Mammalia Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- YLEIFZAVNWDOBM-ZTNXSLBXSA-N ac1l9hc7 Chemical compound C([C@H]12)C[C@@H](C([C@@H](O)CC3)(C)C)[C@@]43C[C@@]14CC[C@@]1(C)[C@@]2(C)C[C@@H]2O[C@]3(O)[C@H](O)C(C)(C)O[C@@H]3[C@@H](C)[C@H]12 YLEIFZAVNWDOBM-ZTNXSLBXSA-N 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- GIJQYGDVOAKOQM-UHFFFAOYSA-N diethoxymethoxyethane Chemical compound CCOC(OCC)OCC.CCOC(OCC)OCC GIJQYGDVOAKOQM-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002451 electron ionisation mass spectrometry Methods 0.000 description 1
- 125000003563 glycoside group Chemical group 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- JFLRBGOBOJWPHI-UHFFFAOYSA-N pyridin-1-ium-1-sulfonate Chemical compound [O-]S(=O)(=O)[N+]1=CC=CC=C1 JFLRBGOBOJWPHI-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
Images
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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Indicating Measured Values (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8902709.8 | 1989-02-07 | ||
| GB898902709A GB8902709D0 (en) | 1989-02-07 | 1989-02-07 | New 4'-epi-4'-amino anthracyclines |
| PCT/EP1990/000183 WO1990009392A1 (en) | 1989-02-07 | 1990-02-02 | New 4'-epi-4'-amino anthracyclines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2073681C1 true RU2073681C1 (ru) | 1997-02-20 |
Family
ID=10651266
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU905001277A RU2073681C1 (ru) | 1989-02-07 | 1990-02-02 | Антрациклиновый гликозид и способы его получения |
Country Status (21)
| Country | Link |
|---|---|
| EP (1) | EP0381989B1 (enExample) |
| JP (1) | JP3000562B2 (enExample) |
| KR (1) | KR920701227A (enExample) |
| AT (1) | ATE72445T1 (enExample) |
| AU (1) | AU628478B2 (enExample) |
| CA (1) | CA2046645A1 (enExample) |
| DE (1) | DE69000019D1 (enExample) |
| DK (1) | DK0381989T3 (enExample) |
| ES (1) | ES2041050T3 (enExample) |
| FI (1) | FI96605C (enExample) |
| GB (1) | GB8902709D0 (enExample) |
| GR (1) | GR3003873T3 (enExample) |
| HU (1) | HU206700B (enExample) |
| IE (1) | IE62307B1 (enExample) |
| IL (1) | IL93258A (enExample) |
| MY (1) | MY105541A (enExample) |
| NZ (1) | NZ232305A (enExample) |
| PT (1) | PT93071B (enExample) |
| RU (1) | RU2073681C1 (enExample) |
| WO (1) | WO1990009392A1 (enExample) |
| ZA (1) | ZA90835B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2286994C2 (ru) * | 2000-11-16 | 2006-11-10 | Менарини Ричерче С.П.А. | Способ получения оптически активного тетралина |
| RU2618523C2 (ru) * | 2012-11-05 | 2017-05-04 | Пфайзер Инк. | Аналоги сплицеостатина |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1241927B (it) * | 1990-05-14 | 1994-02-01 | Menarini Farma Ind | 3'-deamino-4'-deossi-4'-amino-8-fluoroantra- cicline processi per la loro preparazione e composizioni farmaceutiche che le contengono |
| CN1089071C (zh) * | 1999-10-11 | 2002-08-14 | 葛水生 | 铁路列车卫星电视系统 |
| JP5105403B2 (ja) | 2006-12-06 | 2012-12-26 | 日本サーモスタット株式会社 | 感温インジケータ |
| EP2991993B1 (en) * | 2013-04-29 | 2018-06-06 | Nerviano Medical Sciences S.r.l. | Morpholinyl anthracycline derivatives |
| EP3215513B1 (en) | 2014-11-05 | 2019-05-08 | Nerviano Medical Sciences S.r.l. | Functionalized morpholinyl anthracycline derivatives |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57106695A (en) * | 1980-11-01 | 1982-07-02 | Erba Carlo Spa | Anthracycline g lycoside compound |
| GB2091243B (en) * | 1981-01-21 | 1984-06-20 | Erba Farmitalia | Anthracycline glycosides |
| GB8803076D0 (en) * | 1988-02-10 | 1988-03-09 | Erba Carlo Spa | 3'-deamino-4'-deoxy-4'-amino anthracyclines |
-
1989
- 1989-02-07 GB GB898902709A patent/GB8902709D0/en active Pending
-
1990
- 1990-01-23 DE DE9090101309T patent/DE69000019D1/de not_active Expired - Lifetime
- 1990-01-23 ES ES199090101309T patent/ES2041050T3/es not_active Expired - Lifetime
- 1990-01-23 DK DK90101309.4T patent/DK0381989T3/da active
- 1990-01-23 EP EP90101309A patent/EP0381989B1/en not_active Expired - Lifetime
- 1990-01-23 AT AT90101309T patent/ATE72445T1/de not_active IP Right Cessation
- 1990-01-31 NZ NZ232305A patent/NZ232305A/xx unknown
- 1990-02-02 RU SU905001277A patent/RU2073681C1/ru active
- 1990-02-02 JP JP2502349A patent/JP3000562B2/ja not_active Expired - Fee Related
- 1990-02-02 HU HU901678A patent/HU206700B/hu not_active IP Right Cessation
- 1990-02-02 IL IL9325890A patent/IL93258A/en not_active IP Right Cessation
- 1990-02-02 AU AU49510/90A patent/AU628478B2/en not_active Ceased
- 1990-02-02 CA CA002046645A patent/CA2046645A1/en not_active Abandoned
- 1990-02-02 WO PCT/EP1990/000183 patent/WO1990009392A1/en not_active Ceased
- 1990-02-02 MY MYPI90000164A patent/MY105541A/en unknown
- 1990-02-02 KR KR1019910700835A patent/KR920701227A/ko not_active Ceased
- 1990-02-05 IE IE40390A patent/IE62307B1/en not_active IP Right Cessation
- 1990-02-05 ZA ZA90835A patent/ZA90835B/xx unknown
- 1990-02-06 PT PT93071A patent/PT93071B/pt active IP Right Grant
-
1991
- 1991-08-02 FI FI913699A patent/FI96605C/fi active
-
1992
- 1992-02-21 GR GR920400293T patent/GR3003873T3/el unknown
Non-Patent Citations (1)
| Title |
|---|
| Европейский патент N 0051280, кл. С 07 Н 15/252, 1982. Патент Великобритании N 2091243 кл. С 07 Н 15/252, 1982. * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2286994C2 (ru) * | 2000-11-16 | 2006-11-10 | Менарини Ричерче С.П.А. | Способ получения оптически активного тетралина |
| RU2618523C2 (ru) * | 2012-11-05 | 2017-05-04 | Пфайзер Инк. | Аналоги сплицеостатина |
Also Published As
| Publication number | Publication date |
|---|---|
| AU4951090A (en) | 1990-09-05 |
| PT93071B (pt) | 1996-01-31 |
| HUT58065A (en) | 1992-01-28 |
| WO1990009392A1 (en) | 1990-08-23 |
| FI96605B (fi) | 1996-04-15 |
| CA2046645A1 (en) | 1990-08-08 |
| IL93258A0 (en) | 1990-11-29 |
| HU206700B (en) | 1992-12-28 |
| ES2041050T3 (es) | 1993-11-01 |
| GR3003873T3 (enExample) | 1993-03-16 |
| NZ232305A (en) | 1991-11-26 |
| MY105541A (en) | 1994-10-31 |
| FI96605C (fi) | 1996-07-25 |
| FI913699A0 (fi) | 1991-08-02 |
| GB8902709D0 (en) | 1989-03-30 |
| IE900403L (en) | 1990-08-07 |
| EP0381989A1 (en) | 1990-08-16 |
| JP3000562B2 (ja) | 2000-01-17 |
| AU628478B2 (en) | 1992-09-17 |
| DK0381989T3 (da) | 1992-03-23 |
| EP0381989B1 (en) | 1992-02-05 |
| ATE72445T1 (de) | 1992-02-15 |
| IL93258A (en) | 1994-05-30 |
| PT93071A (pt) | 1990-08-31 |
| IE62307B1 (en) | 1995-01-25 |
| JPH04503210A (ja) | 1992-06-11 |
| ZA90835B (en) | 1990-11-28 |
| DE69000019D1 (en) | 1992-03-19 |
| KR920701227A (ko) | 1992-08-11 |
| HU901678D0 (en) | 1991-11-28 |
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