CH623830A5 - - Google Patents
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- Publication number
- CH623830A5 CH623830A5 CH785176A CH785176A CH623830A5 CH 623830 A5 CH623830 A5 CH 623830A5 CH 785176 A CH785176 A CH 785176A CH 785176 A CH785176 A CH 785176A CH 623830 A5 CH623830 A5 CH 623830A5
- Authority
- CH
- Switzerland
- Prior art keywords
- adriamycin
- glycolate
- general formula
- carbon atoms
- leukemia
- Prior art date
Links
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 239000002798 polar solvent Substances 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin 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(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 53
- 229940009456 adriamycin Drugs 0.000 description 24
- 208000032839 leukemia Diseases 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 208000006268 Sarcoma 180 Diseases 0.000 description 8
- 206010003445 Ascites Diseases 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 206010028980 Neoplasm Diseases 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000000259 anti-tumor effect Effects 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 231100001231 less toxic Toxicity 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 101000679555 Homo sapiens TOX high mobility group box family member 2 Proteins 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 241000713862 Moloney murine sarcoma virus Species 0.000 description 2
- 102100022611 TOX high mobility group box family member 2 Human genes 0.000 description 2
- 101150078083 TRI5 gene Proteins 0.000 description 2
- 238000011888 autopsy Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 210000002950 fibroblast Anatomy 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 210000001161 mammalian embryo Anatomy 0.000 description 2
- -1 organic acid salt Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000035755 proliferation Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000004083 survival effect Effects 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- YFUSUXATWLGGNN-UHFFFAOYSA-N (2-hydroxyacetyl) dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC(=O)CO YFUSUXATWLGGNN-UHFFFAOYSA-N 0.000 description 1
- AFGZBIIMQZGNNM-UHFFFAOYSA-N (2-hydroxyacetyl) hexanoate Chemical compound CCCCCC(=O)OC(=O)CO AFGZBIIMQZGNNM-UHFFFAOYSA-N 0.000 description 1
- QSYXYZBUUZSDBF-UHFFFAOYSA-N (2-hydroxyacetyl) octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(=O)CO QSYXYZBUUZSDBF-UHFFFAOYSA-N 0.000 description 1
- 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 1
- DVTZXLCXEVRHKD-UHFFFAOYSA-M C(CCCCC)(=O)C(C(=O)[O-])S.[K+] Chemical compound C(CCCCC)(=O)C(C(=O)[O-])S.[K+] DVTZXLCXEVRHKD-UHFFFAOYSA-M 0.000 description 1
- NFTDQBMORPSSMI-UHFFFAOYSA-M C(CCCCCCCCCCCCCCCCC)(=O)C(C(=O)[O-])O.[K+] Chemical compound C(CCCCCCCCCCCCCCCCC)(=O)C(C(=O)[O-])O.[K+] NFTDQBMORPSSMI-UHFFFAOYSA-M 0.000 description 1
- YPXACOFDROMRQA-UHFFFAOYSA-N C(CO)(=O)OC(CCCCC)=O.[K] Chemical compound C(CO)(=O)OC(CCCCC)=O.[K] YPXACOFDROMRQA-UHFFFAOYSA-N 0.000 description 1
- BZYKIUDRHPWFQZ-UHFFFAOYSA-N C(CO)(=O)OC(CCCCCCCCCCC)=O.[K] Chemical compound C(CO)(=O)OC(CCCCCCCCCCC)=O.[K] BZYKIUDRHPWFQZ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 1
- 206010039491 Sarcoma Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical class 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 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 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- TZZCUXOGTUHMPR-UHFFFAOYSA-M potassium;2-(hexanoylamino)acetate Chemical compound [K+].CCCCCC(=O)NCC([O-])=O TZZCUXOGTUHMPR-UHFFFAOYSA-M 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000004614 tumor growth Effects 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biotechnology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB26271/75A GB1499026A (en) | 1975-06-20 | 1975-06-20 | Adriamycin esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH623830A5 true CH623830A5 (da) | 1981-06-30 |
Family
ID=10241028
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH785176A CH623830A5 (da) | 1975-06-20 | 1976-06-18 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4031211A (da) |
| JP (1) | JPS525756A (da) |
| AT (1) | AT342772B (da) |
| AU (1) | AU502848B2 (da) |
| BE (1) | BE843120A (da) |
| CA (1) | CA1047032A (da) |
| CH (1) | CH623830A5 (da) |
| DE (1) | DE2627146C3 (da) |
| DK (1) | DK270876A (da) |
| FR (1) | FR2314727A1 (da) |
| GB (1) | GB1499026A (da) |
| NL (1) | NL7606455A (da) |
| SE (1) | SE7606971L (da) |
| SU (1) | SU667143A3 (da) |
| ZA (1) | ZA763548B (da) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL170737C (nl) * | 1975-11-12 | 1982-12-16 | Rhone Poulenc Ind | Werkwijze voor het bereiden van tegen tumoren werkzame esters van adriamycine, alsmede voor het bereiden van geneesmiddelen met anti-tumoractiviteit. |
| GB1511680A (en) * | 1975-11-18 | 1978-05-24 | Farmaceutici Italia | Daunosaminyl anthracyclinones |
| GB1518390A (en) * | 1976-03-30 | 1978-07-19 | Farmaceutici Italia | Doxorubicin thioesters |
| US4277466A (en) * | 1978-08-29 | 1981-07-07 | Institut International De Pathologie Cellulaire Et Moleculaire | Complexes of DNA and esters derived from daunorubicine, their preparation and use |
| US4348388A (en) * | 1980-04-02 | 1982-09-07 | G.D. Searle & Co. | 11-Amino-11-deoxydaunorubicin and analogs |
| DE3500023A1 (de) * | 1985-01-02 | 1986-07-10 | Farmitalia Carlo Erba S.p.A., Mailand/Milano | 4'-desoxyanthracyclinester |
| DE3500029A1 (de) * | 1985-01-02 | 1986-09-04 | Farmitalia Carlo Erba S.p.A., Mailand/Milano | Anthracyclinester |
| DE3500017A1 (de) * | 1985-01-02 | 1986-07-10 | Farmitalia Carlo Erba S.p.A., Mailand/Milano | 4'-haloanthracyclinester |
| GB2169286A (en) * | 1985-01-05 | 1986-07-09 | Erba Farmitalia | 4'-Deoxy-4'-halodoxorubicin-14-esters |
| GB2169284A (en) * | 1985-01-05 | 1986-07-09 | Erba Farmitalia | 4'-Epidoxorubicin-14-esters |
| GB2169285A (en) * | 1985-01-05 | 1986-07-09 | Erba Farmitalia | 4'-Deoxydoxorubicin-14-esters |
| US4863739A (en) * | 1987-05-19 | 1989-09-05 | Board Of Regents, The University Of Texas System | Liposome compositions of anthracycline derivatives |
| EP0396626A1 (en) * | 1988-01-19 | 1990-11-14 | Board Of Regents, The University Of Texas System | Glycosides, liposomal compositions thereof, and methods for their use |
| EP2423332A1 (en) | 2006-08-25 | 2012-02-29 | Oncotherapy Science, Inc. | Prognostic markers and therapeutic targets for lung cancer |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3803124A (en) * | 1968-04-12 | 1974-04-09 | Farmaceutici It Soc | Process for the preparation of adriamycin and adriamycinone and adriamycin derivatives |
-
1975
- 1975-06-20 GB GB26271/75A patent/GB1499026A/en not_active Expired
-
1976
- 1976-06-10 US US05/694,656 patent/US4031211A/en not_active Expired - Lifetime
- 1976-06-15 FR FR7618063A patent/FR2314727A1/fr active Granted
- 1976-06-15 NL NL7606455A patent/NL7606455A/xx not_active Application Discontinuation
- 1976-06-15 ZA ZA763548A patent/ZA763548B/xx unknown
- 1976-06-16 AT AT440876A patent/AT342772B/de active
- 1976-06-16 DE DE762627146A patent/DE2627146C3/de not_active Expired
- 1976-06-17 SE SE7606971A patent/SE7606971L/xx not_active Application Discontinuation
- 1976-06-17 DK DK270876A patent/DK270876A/da not_active Application Discontinuation
- 1976-06-17 JP JP51071683A patent/JPS525756A/ja active Granted
- 1976-06-17 AU AU15007/76A patent/AU502848B2/en not_active Expired
- 1976-06-18 BE BE168067A patent/BE843120A/xx not_active IP Right Cessation
- 1976-06-18 CH CH785176A patent/CH623830A5/de not_active IP Right Cessation
- 1976-06-18 CA CA255,213A patent/CA1047032A/en not_active Expired
- 1976-06-19 SU SU762374706A patent/SU667143A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| AU1500776A (en) | 1977-12-22 |
| AU502848B2 (en) | 1979-08-09 |
| DE2627146A1 (de) | 1976-12-30 |
| CA1047032A (en) | 1979-01-23 |
| JPS525756A (en) | 1977-01-17 |
| DK270876A (da) | 1976-12-21 |
| SE7606971L (sv) | 1976-12-21 |
| AT342772B (de) | 1978-04-25 |
| BE843120A (fr) | 1976-10-18 |
| ATA440876A (de) | 1977-08-15 |
| GB1499026A (en) | 1978-01-25 |
| FR2314727A1 (fr) | 1977-01-14 |
| ZA763548B (en) | 1977-07-27 |
| FR2314727B1 (da) | 1978-10-20 |
| SU667143A3 (ru) | 1979-06-05 |
| US4031211A (en) | 1977-06-21 |
| JPS5610918B2 (da) | 1981-03-11 |
| DE2627146C3 (de) | 1979-03-01 |
| DE2627146B2 (de) | 1978-06-29 |
| NL7606455A (nl) | 1976-12-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |