SE8001616L - Forfarande for framstellning av glykosidforening - Google Patents
Forfarande for framstellning av glykosidforeningInfo
- Publication number
- SE8001616L SE8001616L SE8001616A SE8001616A SE8001616L SE 8001616 L SE8001616 L SE 8001616L SE 8001616 A SE8001616 A SE 8001616A SE 8001616 A SE8001616 A SE 8001616A SE 8001616 L SE8001616 L SE 8001616L
- Authority
- SE
- Sweden
- Prior art keywords
- procedure
- glycoside compound
- deoxy
- hydrochloride
- treated
- Prior art date
Links
- 229930182470 glycoside Natural products 0.000 title claims 2
- -1 GLYCOSIDE COMPOUND Chemical class 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 239000004280 Sodium formate Substances 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 150000002338 glycosides Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 claims 1
- 235000019254 sodium formate Nutrition 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract 2
- GWFZKHINCFHION-HCPKQARPSA-N (7s,9s)-9-acetyl-7-[(2r,4s,6r)-4-amino-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione;hydrochloride Chemical compound Cl.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[C@@H](C)O1 GWFZKHINCFHION-HCPKQARPSA-N 0.000 abstract 1
- ITSGNOIFAJAQHJ-UHFFFAOYSA-N 7-(4-amino-6-methyloxan-2-yl)oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione Chemical compound C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(=O)CO)CC1OC1CC(N)CC(C)O1 ITSGNOIFAJAQHJ-UHFFFAOYSA-N 0.000 abstract 1
- TWCMVXMQHSVIOJ-UHFFFAOYSA-N Aglycone of yadanzioside D Natural products COC(=O)C12OCC34C(CC5C(=CC(O)C(O)C5(C)C3C(O)C1O)C)OC(=O)C(OC(=O)C)C24 TWCMVXMQHSVIOJ-UHFFFAOYSA-N 0.000 abstract 1
- PLMKQQMDOMTZGG-UHFFFAOYSA-N Astrantiagenin E-methylester Natural products CC12CCC(O)C(C)(CO)C1CCC1(C)C2CC=C2C3CC(C)(C)CCC3(C(=O)OC)CCC21C PLMKQQMDOMTZGG-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 230000000259 anti-tumor effect Effects 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- PFOARMALXZGCHY-UHFFFAOYSA-N homoegonol Natural products C1=C(OC)C(OC)=CC=C1C1=CC2=CC(CCCO)=CC(OC)=C2O1 PFOARMALXZGCHY-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/14—Nitrogen atoms not forming part of a nitro radical
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
Claims (1)
1. Farfarande for framst011ning av 4'-deoxiadri.amycinhydrok1orid med formeln I: lost i en blandning av metanol och dioxan behandlas med brom fbr erhallande av 14-bromderivat-me11anpr0dukten vilken behandlas med en vattenhaltig natriumformeatlosning yid rumstemperatur under omkring 100 timmar varvid 4'-deoxiadriamycin erhalles som glykosidbas vilken slutligen isoleras son hydrok1orid.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB39471/75A GB1511559A (en) | 1975-09-26 | 1975-09-26 | Anthracycline glycosides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE8001616L true SE8001616L (sv) | 1980-02-29 |
| SE435514B SE435514B (sv) | 1984-10-01 |
Family
ID=10409731
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7610564A SE429655B (sv) | 1975-09-26 | 1976-09-23 | Forfarande for framstellning av 4'-deoxidauromycin hydroklorid |
| SE8001616A SE435514B (sv) | 1975-09-26 | 1980-02-29 | Forfarande for framstellning av 4'-deoxiadriamycin hydroklorid |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7610564A SE429655B (sv) | 1975-09-26 | 1976-09-23 | Forfarande for framstellning av 4'-deoxidauromycin hydroklorid |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4067969A (sv) |
| JP (1) | JPS5242869A (sv) |
| AT (1) | AT347582B (sv) |
| AU (1) | AU504480B2 (sv) |
| BE (1) | BE846548A (sv) |
| CA (1) | CA1060002A (sv) |
| CH (1) | CH606082A5 (sv) |
| DE (1) | DE2642837C3 (sv) |
| DK (1) | DK146626C (sv) |
| FR (1) | FR2325659A1 (sv) |
| GB (1) | GB1511559A (sv) |
| HK (1) | HK1182A (sv) |
| NL (1) | NL174015C (sv) |
| SE (2) | SE429655B (sv) |
| SU (2) | SU670226A3 (sv) |
| ZA (1) | ZA765736B (sv) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1567456A (en) * | 1976-11-16 | 1980-05-14 | Farmaceutici Italia | Daunomycin derivatives |
| GB1550879A (en) * | 1976-12-22 | 1979-08-22 | Farmaceutici Italia | Antitumour glycosides |
| US4362720A (en) * | 1977-04-14 | 1982-12-07 | Chembiomed Ltd. | Synthesis of 2-amino-2-deoxyglycoses and 2-amino-2-deoxyglycosides from glycals |
| GB1573037A (en) * | 1977-05-05 | 1980-08-13 | Farmaceutici Italia | Anthracyclines |
| GB1573036A (en) * | 1977-05-05 | 1980-08-13 | Farmaceutici Italia | Anthracyclines |
| US4201773A (en) * | 1978-07-26 | 1980-05-06 | The United States Of America As Represented By The Department Of Health, Education And Welfare | 7-O-(2,6-Dideoxy-α-L-lyxo-hexopyranosyl)-daunomycinone, desmethoxy daunomycinone, adriamycinone, and carminomycinone |
| US4259476A (en) * | 1979-04-02 | 1981-03-31 | Kende Andrew S | Novel heterocyclic anthracycline compounds |
| EP0024727B1 (en) * | 1979-09-01 | 1982-05-26 | FARMITALIA CARLO ERBA S.p.A. | Anthracycline glycosides, processes for their preparation and pharmaceutical composition containing them |
| CA1174669A (en) * | 1980-07-18 | 1984-09-18 | Michael J. Broadhurst | Anthracycline glycosides |
| ZA814722B (en) * | 1980-07-18 | 1982-07-28 | Hoffmann La Roche | Novel anthracycline glycosides |
| 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 |
| JPS57106694A (en) * | 1980-11-01 | 1982-07-02 | Erba Carlo Spa | Anthracycline glycoside |
| JPS57106695A (en) * | 1980-11-01 | 1982-07-02 | Erba Carlo Spa | Anthracycline g lycoside compound |
| JPS57142981A (en) * | 1981-01-21 | 1982-09-03 | Erba Carlo Spa | Anthracycline glycoside, manufacture and tumor generation inhibiting drug containing same |
| DE3200809C2 (de) * | 1981-01-21 | 1986-08-28 | Farmitalia Carlo Erba S.p.A., Mailand/Milano | 4'-Desoxy-3'-epi-daunorubicin und -doxorubicin, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| US4325947A (en) * | 1981-05-12 | 1982-04-20 | Farmitalia Carlo Erba S.P.A. | 4-Demethoxy-4'-deoxydoxorubicin |
| AU554416B2 (en) * | 1982-05-24 | 1986-08-21 | Farmitalia Carlo Erba S.P.A. | Anthracycline glycosides |
| US4562177A (en) * | 1982-08-17 | 1985-12-31 | The Ohio State University Research Foundation | 3'-Amino-2' halo-anthracycline antibiotics |
| US4514561A (en) * | 1983-04-15 | 1985-04-30 | Research Corporation | Process for preparing α-L N-acetyl daunosaminide |
| DE3500023A1 (de) * | 1985-01-02 | 1986-07-10 | Farmitalia Carlo Erba S.p.A., Mailand/Milano | 4'-desoxyanthracyclinester |
| GB2169285A (en) * | 1985-01-05 | 1986-07-09 | Erba Farmitalia | 4'-Deoxydoxorubicin-14-esters |
| US5124317A (en) * | 1985-08-02 | 1992-06-23 | Farmitalia Carlo Erba S.P.A. | Injectable ready-to-use solutions containing an antitumor anthracycline glycoside |
| GB8519452D0 (en) * | 1985-08-02 | 1985-09-11 | Erba Farmitalia | Injectable solutions |
| GB8708927D0 (en) * | 1987-04-14 | 1987-05-20 | Erba Farmitalia | Chiral synthesis of anthracyclines |
| NZ224252A (en) | 1987-04-21 | 1991-09-25 | Erba Carlo Spa | An anthracycline glycoside and its preparation |
| GB2212154B (en) * | 1987-11-10 | 1991-03-27 | Erba Carlo Spa | New 4-demethoxy anthracycline derivatives |
| AU608415B2 (en) * | 1988-01-19 | 1991-03-28 | University Of Texas System, The | Esters of 3'-deaminodoxorubicin, liposomal compositions thereof |
| GB8803076D0 (en) * | 1988-02-10 | 1988-03-09 | Erba Carlo Spa | 3'-deamino-4'-deoxy-4'-amino anthracyclines |
| WO1990007519A1 (en) * | 1988-12-28 | 1990-07-12 | Board Of Regents, The University Of Texas System | 3'-deamino analogs of esorubicin and methods for their use |
| US5948896A (en) * | 1997-08-13 | 1999-09-07 | Gem Pharmaceuticals | Processes for preparing 13-deoxy anthracycline derivatives |
| US5942605A (en) * | 1998-03-03 | 1999-08-24 | Gem Pharmaceuticals, Inc. | 5-imino-13-deoxy anthracycline derivatives, their uses, and processes for preparing them |
Family Cites Families (4)
| 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 |
| DE1792346C3 (de) * | 1968-08-22 | 1980-10-23 | Rotta Research Laboratorium S.P.A., San Fruttuoso Di Monza, Mailand (Italien) | Pharmazeutisches Präparat für die Behandlung von degenerativen Gelenkerkrankungen |
| FR2183710A1 (en) * | 1972-05-06 | 1973-12-21 | Farmaceutici Italia | Daunomycin (hydrochloride) prepn - by reaction of daunomycinone with daunosamines, useful as antitumour agent and anti-leucemic |
| US4020270A (en) * | 1974-05-02 | 1977-04-26 | Societa' Farmaceutici Italia S.P.A. | L-lyxohex-1-enopyranose derivative |
-
1975
- 1975-09-26 GB GB39471/75A patent/GB1511559A/en not_active Expired
-
1976
- 1976-09-13 NL NLAANVRAGE7610139,A patent/NL174015C/xx not_active IP Right Cessation
- 1976-09-13 US US05/722,689 patent/US4067969A/en not_active Expired - Lifetime
- 1976-09-22 DK DK426076A patent/DK146626C/da not_active IP Right Cessation
- 1976-09-22 AU AU18025/76A patent/AU504480B2/en not_active Expired
- 1976-09-23 CA CA261,920A patent/CA1060002A/en not_active Expired
- 1976-09-23 SE SE7610564A patent/SE429655B/sv not_active IP Right Cessation
- 1976-09-23 DE DE2642837A patent/DE2642837C3/de not_active Expired
- 1976-09-23 AT AT707276A patent/AT347582B/de not_active IP Right Cessation
- 1976-09-23 FR FR7628582A patent/FR2325659A1/fr active Granted
- 1976-09-24 ZA ZA765736A patent/ZA765736B/xx unknown
- 1976-09-24 BE BE170901A patent/BE846548A/xx not_active IP Right Cessation
- 1976-09-24 JP JP51115356A patent/JPS5242869A/ja active Granted
- 1976-09-24 CH CH1215876A patent/CH606082A5/xx not_active IP Right Cessation
- 1976-09-24 SU SU762403408A patent/SU670226A3/ru active
-
1977
- 1977-09-22 SU SU772523451A patent/SU730310A3/ru active
-
1980
- 1980-02-29 SE SE8001616A patent/SE435514B/sv not_active IP Right Cessation
-
1982
- 1982-01-14 HK HK11/82A patent/HK1182A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA1060002A (en) | 1979-08-07 |
| DE2642837A1 (de) | 1977-04-07 |
| SE7610564L (sv) | 1977-03-27 |
| ZA765736B (en) | 1977-11-30 |
| DK146626C (da) | 1984-04-30 |
| DK426076A (da) | 1977-03-27 |
| SU730310A3 (ru) | 1980-04-25 |
| NL7610139A (nl) | 1977-03-29 |
| SE429655B (sv) | 1983-09-19 |
| BE846548A (fr) | 1977-03-24 |
| SE435514B (sv) | 1984-10-01 |
| FR2325659A1 (fr) | 1977-04-22 |
| JPS5242869A (en) | 1977-04-04 |
| NL174015C (nl) | 1984-04-16 |
| AU1802576A (en) | 1978-04-06 |
| DK146626B (da) | 1983-11-21 |
| NL174015B (nl) | 1983-11-16 |
| GB1511559A (en) | 1978-05-24 |
| DE2642837B2 (de) | 1982-01-07 |
| CH606082A5 (sv) | 1978-10-13 |
| DE2642837C3 (de) | 1982-08-12 |
| SU670226A3 (ru) | 1979-06-25 |
| FR2325659B1 (sv) | 1982-08-20 |
| ATA707276A (de) | 1978-05-15 |
| AT347582B (de) | 1979-01-10 |
| HK1182A (en) | 1982-01-22 |
| AU504480B2 (en) | 1979-10-18 |
| JPS6123189B2 (sv) | 1986-06-04 |
| US4067969A (en) | 1978-01-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NAL | Patent in force |
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