DE2751395C2 - Anthracyclindisaccharide und deren Verwendung - Google Patents
Anthracyclindisaccharide und deren VerwendungInfo
- Publication number
- DE2751395C2 DE2751395C2 DE2751395A DE2751395A DE2751395C2 DE 2751395 C2 DE2751395 C2 DE 2751395C2 DE 2751395 A DE2751395 A DE 2751395A DE 2751395 A DE2751395 A DE 2751395A DE 2751395 C2 DE2751395 C2 DE 2751395C2
- Authority
- DE
- Germany
- Prior art keywords
- daunomycin
- anthracycline
- disaccharides
- trifluoroacetyldaunomycin
- merck
- 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
- 150000002016 disaccharides Chemical class 0.000 title claims description 7
- 229940045799 anthracyclines and related substance Drugs 0.000 title claims description 5
- 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 claims description 10
- 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 claims description 7
- 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 claims description 6
- 206010028980 Neoplasm Diseases 0.000 claims description 5
- 201000011510 cancer Diseases 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 230000004083 survival effect Effects 0.000 description 3
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
- 239000000203 mixture Substances 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 208000028018 Lymphocytic leukaemia Diseases 0.000 description 1
- 230000000118 anti-neoplastic effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- -1 halogen sugars Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 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 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000002054 transplantation 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)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (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 |
|---|---|
| DE2751395A1 DE2751395A1 (de) | 1978-05-18 |
| DE2751395C2 true DE2751395C2 (de) | 1982-10-28 |
Family
ID=10446415
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2751395A Expired DE2751395C2 (de) | 1976-11-17 | 1977-11-17 | Anthracyclindisaccharide und deren Verwendung |
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 DK DK503077A patent/DK503077A/da not_active Application Discontinuation
- 1977-11-14 AT AT812177A patent/AT352281B/de active
- 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 CA CA290,706A patent/CA1080702A/en not_active Expired
- 1977-11-14 YU YU02713/77A patent/YU271377A/xx unknown
- 1977-11-14 IE IE2314/77A patent/IE46166B1/en unknown
- 1977-11-15 CH CH1396277A patent/CH630929A5/de not_active IP Right Cessation
- 1977-11-15 FR FR7734247A patent/FR2371461A1/fr active Granted
- 1977-11-15 AU AU30663/77A patent/AU518396B2/en not_active Expired
- 1977-11-16 BE BE182627A patent/BE860843A/xx not_active IP Right Cessation
- 1977-11-16 JP JP13776077A patent/JPS5363367A/ja active Pending
- 1977-11-16 ZA ZA00776842A patent/ZA776842B/xx unknown
- 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 |
|---|---|
| YU271377A (en) | 1982-06-30 |
| NL7712296A (en) | 1978-05-19 |
| IE46166L (en) | 1978-05-17 |
| AU3066377A (en) | 1979-05-24 |
| FR2371461A1 (fr) | 1978-06-16 |
| IE46166B1 (en) | 1983-03-09 |
| FR2371461B1 (enExample) | 1981-11-20 |
| SE7712862L (sv) | 1978-05-18 |
| DE2751395A1 (de) | 1978-05-18 |
| DK503077A (da) | 1978-05-18 |
| CH630929A5 (de) | 1982-07-15 |
| NZ185678A (en) | 1978-12-18 |
| US4169142A (en) | 1979-09-25 |
| AU518396B2 (en) | 1981-10-01 |
| ATA812177A (de) | 1979-02-15 |
| ZA776842B (en) | 1978-11-29 |
| JPS5363367A (en) | 1978-06-06 |
| BE860843A (fr) | 1978-05-16 |
| CA1080702A (en) | 1980-07-01 |
| GB1561507A (en) | 1980-02-20 |
| AT352281B (de) | 1979-09-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8127 | New person/name/address of the applicant |
Owner name: FARMITALIA CARLO ERBA S.P.A., 20159 MILANO, IT |
|
| D2 | Grant after examination | ||
| 8339 | Ceased/non-payment of the annual fee |