IE46166B1 - Atnhracycline disaccharides - Google Patents
Atnhracycline disaccharidesInfo
- Publication number
- IE46166B1 IE46166B1 IE2314/77A IE231477A IE46166B1 IE 46166 B1 IE46166 B1 IE 46166B1 IE 2314/77 A IE2314/77 A IE 2314/77A IE 231477 A IE231477 A IE 231477A IE 46166 B1 IE46166 B1 IE 46166B1
- Authority
- IE
- Ireland
- Prior art keywords
- protected
- daunomycin
- process according
- general formula
- halogeno
- Prior art date
Links
- 150000002016 disaccharides Chemical class 0.000 title claims abstract description 7
- 229940045799 anthracyclines and related substance Drugs 0.000 claims abstract description 6
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000003054 catalyst Substances 0.000 claims abstract description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- 229930182470 glycoside Natural products 0.000 claims description 6
- 150000002338 glycosides Chemical class 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 2
- QRUBYZBWAOOHSV-UHFFFAOYSA-M silver trifluoromethanesulfonate Chemical group [Ag+].[O-]S(=O)(=O)C(F)(F)F QRUBYZBWAOOHSV-UHFFFAOYSA-M 0.000 claims description 2
- -1 anthracyline disaccharide Chemical class 0.000 claims 1
- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 claims 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims 1
- 230000000259 anti-tumor effect Effects 0.000 abstract description 2
- 238000005904 alkaline hydrolysis reaction Methods 0.000 abstract 1
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 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 5
- 239000000047 product Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 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 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 238000003756 stirring Methods 0.000 description 4
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000002808 molecular sieve Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
- QTGKDZKONUUXOU-RPYJURNCSA-N (7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-[(2S,4S,5S,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione Chemical compound COc1cccc2C(=O)c3c(O)c4C[C@](O)(C[C@H](O[C@H]5C[C@H](N)[C@H](O[C@H]6C[C@H](O)[C@H](O)[C@H](C)O6)[C@H](C)O5)c4c(O)c3C(=O)c12)C(C)=O QTGKDZKONUUXOU-RPYJURNCSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 208000028018 Lymphocytic leukaemia Diseases 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 230000002927 anti-mitotic effect Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- 239000006227 byproduct Substances 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- WPJRFCZKZXBUNI-HCWXCVPCSA-N daunosamine Chemical compound C[C@H](O)[C@@H](O)[C@@H](N)CC=O WPJRFCZKZXBUNI-HCWXCVPCSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 208000003747 lymphoid leukemia Diseases 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 210000004881 tumor cell Anatomy 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)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biotechnology (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB47835/76A GB1561507A (en) | 1976-11-17 | 1976-11-17 | Snthracycline disaccharides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE46166L IE46166L (en) | 1978-05-17 |
| IE46166B1 true IE46166B1 (en) | 1983-03-09 |
Family
ID=10446415
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2314/77A IE46166B1 (en) | 1976-11-17 | 1977-11-14 | Atnhracycline disaccharides |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4169142A (enExample) |
| JP (1) | JPS5363367A (enExample) |
| AT (1) | AT352281B (enExample) |
| AU (1) | AU518396B2 (enExample) |
| BE (1) | BE860843A (enExample) |
| CA (1) | CA1080702A (enExample) |
| CH (1) | CH630929A5 (enExample) |
| DE (1) | DE2751395C2 (enExample) |
| DK (1) | DK503077A (enExample) |
| FR (1) | FR2371461A1 (enExample) |
| GB (1) | GB1561507A (enExample) |
| IE (1) | IE46166B1 (enExample) |
| NL (1) | NL7712296A (enExample) |
| NZ (1) | NZ185678A (enExample) |
| SE (1) | SE7712862L (enExample) |
| YU (1) | YU271377A (enExample) |
| ZA (1) | ZA776842B (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK160616C (da) * | 1979-02-03 | 1991-09-02 | Zaidan Hojin Biseibutsu | Fremgangsmaade til fremstilling af anthracyclinderivater eller syreadditionssalte deraf |
| PL124284B1 (en) * | 1979-10-17 | 1983-01-31 | Politechnika Gdanska | Process for preparing n-glycosyl derivatives of antibiotics from anthracyclines group |
| JPS56156300A (en) * | 1980-04-26 | 1981-12-02 | Microbial Chem Res Found | Novel preparative method of anthracyclin derivative |
| JPS57176995A (en) * | 1981-04-23 | 1982-10-30 | Sanraku Inc | Novel anthracyclinone glycoside and its preparation |
| US4918172A (en) * | 1987-10-06 | 1990-04-17 | Sanraku Incorporated | Anthracycline antibiotics |
| US4864859A (en) * | 1988-07-25 | 1989-09-12 | Allied-Signal Inc. | Method for dynamically balancing a mechanism having a high speed rotating component |
| IT1262565B (it) * | 1993-09-30 | 1996-07-04 | Menarini Farma Ind | Disaccaridi di antracicline, loro processi di preparazione e composizioni farmaceutiche che li contengono. |
| US20050208037A1 (en) * | 2003-10-21 | 2005-09-22 | Board Of Regents, The University Of Texas System | Thioredoxin increases redox-cycling of anticancer agents thereby sensitizes cancer cells to apoptosis |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3686163A (en) * | 1968-05-14 | 1972-08-22 | Farmaceutici Italia | Dihydrodaunomycin antibiotic and derivatives thereof |
| GB1470860A (en) * | 1974-10-29 | 1977-04-21 | Farmaceutici Italia | Anthracycline glycosides |
-
1976
- 1976-11-17 GB GB47835/76A patent/GB1561507A/en not_active Expired
-
1977
- 1977-11-08 NL NL7712296A patent/NL7712296A/xx not_active Application Discontinuation
- 1977-11-14 AT AT812177A patent/AT352281B/de active
- 1977-11-14 CA CA290,706A patent/CA1080702A/en not_active Expired
- 1977-11-14 DK DK503077A patent/DK503077A/da not_active Application Discontinuation
- 1977-11-14 IE IE2314/77A patent/IE46166B1/en unknown
- 1977-11-14 US US05/851,165 patent/US4169142A/en not_active Expired - Lifetime
- 1977-11-14 NZ NZ185678A patent/NZ185678A/xx unknown
- 1977-11-14 YU YU02713/77A patent/YU271377A/xx unknown
- 1977-11-15 FR FR7734247A patent/FR2371461A1/fr active Granted
- 1977-11-15 CH CH1396277A patent/CH630929A5/de not_active IP Right Cessation
- 1977-11-15 AU AU30663/77A patent/AU518396B2/en not_active Expired
- 1977-11-16 JP JP13776077A patent/JPS5363367A/ja active Pending
- 1977-11-16 ZA ZA00776842A patent/ZA776842B/xx unknown
- 1977-11-16 BE BE182627A patent/BE860843A/xx not_active IP Right Cessation
- 1977-11-17 SE SE7712862A patent/SE7712862L/ not_active Application Discontinuation
- 1977-11-17 DE DE2751395A patent/DE2751395C2/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| SE7712862L (sv) | 1978-05-18 |
| NZ185678A (en) | 1978-12-18 |
| CA1080702A (en) | 1980-07-01 |
| DE2751395C2 (de) | 1982-10-28 |
| IE46166L (en) | 1978-05-17 |
| ATA812177A (de) | 1979-02-15 |
| GB1561507A (en) | 1980-02-20 |
| BE860843A (fr) | 1978-05-16 |
| DK503077A (da) | 1978-05-18 |
| ZA776842B (en) | 1978-11-29 |
| FR2371461A1 (fr) | 1978-06-16 |
| NL7712296A (en) | 1978-05-19 |
| US4169142A (en) | 1979-09-25 |
| AU3066377A (en) | 1979-05-24 |
| AU518396B2 (en) | 1981-10-01 |
| YU271377A (en) | 1982-06-30 |
| JPS5363367A (en) | 1978-06-06 |
| CH630929A5 (de) | 1982-07-15 |
| FR2371461B1 (enExample) | 1981-11-20 |
| DE2751395A1 (de) | 1978-05-18 |
| AT352281B (de) | 1979-09-10 |
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