GB1509875A - Optically active anthracyclinones and anthracycline glycosides - Google Patents
Optically active anthracyclinones and anthracycline glycosidesInfo
- Publication number
- GB1509875A GB1509875A GB24439/76A GB2443976A GB1509875A GB 1509875 A GB1509875 A GB 1509875A GB 24439/76 A GB24439/76 A GB 24439/76A GB 2443976 A GB2443976 A GB 2443976A GB 1509875 A GB1509875 A GB 1509875A
- Authority
- GB
- United Kingdom
- Prior art keywords
- anthracycline glycosides
- methoxy
- halogen
- methyl
- general formula
- 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
- 229940045799 anthracyclines and related substance Drugs 0.000 title abstract 4
- 229930182470 glycoside Natural products 0.000 title abstract 4
- 150000002338 glycosides Chemical class 0.000 title abstract 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 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 2
- 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 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 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 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 238000005903 acid hydrolysis reaction Methods 0.000 abstract 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 239000000010 aprotic solvent Substances 0.000 abstract 1
- 238000004587 chromatography analysis Methods 0.000 abstract 1
- 238000002425 crystallisation Methods 0.000 abstract 1
- 230000008025 crystallization Effects 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- QRUBYZBWAOOHSV-UHFFFAOYSA-M silver trifluoromethanesulfonate Chemical compound [Ag+].[O-]S(=O)(=O)C(F)(F)F QRUBYZBWAOOHSV-UHFFFAOYSA-M 0.000 abstract 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7617955A FR2355028A1 (fr) | 1976-06-14 | 1976-06-14 | Procede pour la preparation de glycosides derives d'anthracyclines optiquement actives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1509875A true GB1509875A (en) | 1978-05-04 |
Family
ID=9174331
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB24439/76A Expired GB1509875A (en) | 1976-06-14 | 1976-06-12 | Optically active anthracyclinones and anthracycline glycosides |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4107423A (OSRAM) |
| JP (1) | JPS532463A (OSRAM) |
| AT (2) | AT344899B (OSRAM) |
| BE (1) | BE842930A (OSRAM) |
| CA (1) | CA1046510A (OSRAM) |
| CH (1) | CH622529A5 (OSRAM) |
| DE (1) | DE2626783C2 (OSRAM) |
| FR (1) | FR2355028A1 (OSRAM) |
| GB (1) | GB1509875A (OSRAM) |
| NL (2) | NL175300C (OSRAM) |
| SE (2) | SE421318B (OSRAM) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0128670A1 (en) * | 1983-05-13 | 1984-12-19 | Adria Laboratories, Inc. | 4-Demethoxy-3'-deamino-3'(4-morpholinyl) derivatives of anthracycline anticancer antibiotics |
| US4496485A (en) * | 1983-11-25 | 1985-01-29 | G. D. Searle & Co. | Asymmetric 7-O-(substituted acetyl)-4-demethoxydaunomycinones |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1567456A (en) * | 1976-11-16 | 1980-05-14 | Farmaceutici Italia | Daunomycin derivatives |
| IL55431A (en) * | 1978-08-24 | 1982-07-30 | Yeda Res & Dev | Anthracycline type antibiotics,their preparation and pharmaceutical compositions comprising them |
| NL8001417A (nl) * | 1979-03-17 | 1980-09-19 | Erba Farmitalia | Antitumorglycosiden. |
| GB2056443B (en) * | 1979-08-20 | 1984-01-18 | Hoffmann La Roche | Cyclic compounds |
| JPS56135021A (en) * | 1980-03-25 | 1981-10-22 | Nippon Kokan Kk <Nkk> | Lining for internal surface of welded part of steel pipe |
| CA1174669A (en) * | 1980-07-18 | 1984-09-18 | Michael J. Broadhurst | Anthracycline glycosides |
| GB8317037D0 (en) * | 1983-06-23 | 1983-07-27 | Erba Farmitalia | 6-deoxyanthracyclines |
| US4540695A (en) * | 1981-08-12 | 1985-09-10 | Sumitomo Chemical Co., Ltd. | Aminonaphthacene derivatives and their use |
| NL8300150A (nl) * | 1982-01-26 | 1983-08-16 | Erba Farmitalia | Daunorubicine en doxorubicine-analoga, hun bereiding en toepassing. |
| DE3317702A1 (de) * | 1982-05-24 | 1983-11-24 | Farmitalia Carlo Erba S.p.A., 20159 Milano | Anthracyclinglykoside, verfahren zu deren herstellung und arzneimittel, welche diese enthalten |
| US4831019A (en) * | 1983-10-31 | 1989-05-16 | Adria Laboratories, Inc. | Pharmaceutical preparations of 4-demethoxy-n-trifluoroacetyl anthracyclines |
| NZ224252A (en) * | 1987-04-21 | 1991-09-25 | Erba Carlo Spa | An anthracycline glycoside and its preparation |
| GB8803301D0 (en) * | 1988-02-12 | 1988-03-09 | Erba Carlo Spa | Process for preparation of 4-demethoxy-daunomycinone aglycone of 4-demethoxy-daunorubicin |
| GB9418260D0 (en) * | 1994-09-09 | 1994-10-26 | Erba Carlo Spa | Anthracycline derivatives |
| DE10155016A1 (de) * | 2001-11-07 | 2003-05-15 | Knoell Hans Forschung Ev | Neue Chinon-Verbindung, Verfahren zur Herstellung und deren Verwendung |
| US8173621B2 (en) | 2008-06-11 | 2012-05-08 | Gilead Pharmasset Llc | Nucleoside cyclicphosphates |
| SG172363A1 (en) | 2008-12-23 | 2011-07-28 | Pharmasset Inc | Synthesis of purine nucleosides |
| CN102753563A (zh) * | 2008-12-23 | 2012-10-24 | 吉利德制药有限责任公司 | 核苷类似物 |
| AR074897A1 (es) | 2008-12-23 | 2011-02-23 | Pharmasset Inc | Fosforamidatos de nucleosidos |
| WO2011123668A2 (en) | 2010-03-31 | 2011-10-06 | Pharmasset, Inc. | Stereoselective synthesis of phosphorus containing actives |
| US8846882B2 (en) * | 2011-04-29 | 2014-09-30 | Synbias Pharma Ag | Method of producing 4-demethoxydaunorubicin |
| CN104151376B (zh) * | 2014-06-23 | 2017-02-08 | 天津药物研究院新药评价有限公司 | 一种抗肿瘤药物及其合成方法和用途 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3427300A (en) * | 1965-11-12 | 1969-02-11 | Merck & Co Inc | Anti-inflammatory steroid 2'-acetamido-2'-deoxy-glucoside compounds |
| YU33730B (en) * | 1967-04-18 | 1978-02-28 | Farmaceutici Italia | Process for preparing a novel antibiotic substance and salts thereof |
| US3803124A (en) * | 1968-04-12 | 1974-04-09 | Farmaceutici It Soc | Process for the preparation of adriamycin and adriamycinone and adriamycin derivatives |
| US3629231A (en) * | 1968-05-23 | 1971-12-21 | Biorex Laboratories Ltd | Derivatives of glycyrrhetinic acid |
| FI51808C (fi) * | 1968-07-15 | 1977-04-12 | Rhone Poulenc Sa | Menetelmä uusien kasvainten naftaseenijohdannaisten valmistamiseksi. |
| GB1467383A (en) * | 1974-06-12 | 1977-03-16 | Farmaceutici Italia | Daunomycin analogues |
| US4039663A (en) * | 1975-03-19 | 1977-08-02 | Societa' Farmaceutici Italia S.P.A. | Daunomycins, process for their uses and intermediates |
-
1976
- 1976-06-12 GB GB24439/76A patent/GB1509875A/en not_active Expired
- 1976-06-14 FR FR7617955A patent/FR2355028A1/fr active Granted
- 1976-06-14 BE BE167900A patent/BE842930A/xx not_active IP Right Cessation
- 1976-06-15 SE SE7606808A patent/SE421318B/xx active Protection Beyond IP Right Term
- 1976-06-15 DE DE2626783A patent/DE2626783C2/de not_active Expired
- 1976-06-16 CH CH769276A patent/CH622529A5/de not_active IP Right Cessation
- 1976-06-21 AT AT450676A patent/AT344899B/de active Protection Beyond IP Right Term
- 1976-06-21 AT AT636377A patent/AT345461B/de not_active IP Right Cessation
- 1976-06-24 NL NLAANVRAGE7606897,A patent/NL175300C/xx not_active IP Right Cessation
- 1976-06-25 JP JP7454176A patent/JPS532463A/ja active Granted
- 1976-06-29 CA CA255,970A patent/CA1046510A/en not_active Expired
- 1976-08-14 US US05/695,434 patent/US4107423A/en not_active Expired - Lifetime
-
1981
- 1981-01-26 SE SE8100471A patent/SE447988B/sv unknown
-
1993
- 1993-06-24 NL NL930090C patent/NL930090I2/nl unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0128670A1 (en) * | 1983-05-13 | 1984-12-19 | Adria Laboratories, Inc. | 4-Demethoxy-3'-deamino-3'(4-morpholinyl) derivatives of anthracycline anticancer antibiotics |
| US4496485A (en) * | 1983-11-25 | 1985-01-29 | G. D. Searle & Co. | Asymmetric 7-O-(substituted acetyl)-4-demethoxydaunomycinones |
Also Published As
| Publication number | Publication date |
|---|---|
| SE421318B (sv) | 1981-12-14 |
| SE7606808L (sv) | 1977-12-16 |
| NL930090I1 (nl) | 1993-10-01 |
| NL175300B (nl) | 1984-05-16 |
| SE8100471L (sv) | 1981-01-26 |
| DE2626783C2 (de) | 1985-08-14 |
| CA1046510A (en) | 1979-01-16 |
| NL175300C (nl) | 1984-10-16 |
| BE842930A (fr) | 1976-10-01 |
| NL7606897A (nl) | 1977-12-28 |
| JPS532463A (en) | 1978-01-11 |
| US4107423A (en) | 1978-08-15 |
| FR2355028B3 (OSRAM) | 1979-03-02 |
| AT345461B (de) | 1978-09-25 |
| DE2626783A1 (de) | 1977-12-29 |
| ATA450676A (de) | 1977-12-15 |
| CH622529A5 (en) | 1981-04-15 |
| AT344899B (de) | 1978-08-10 |
| JPS6123200B2 (OSRAM) | 1986-06-04 |
| ATA636377A (de) | 1978-01-15 |
| SE447988B (sv) | 1987-01-12 |
| NL930090I2 (nl) | 1994-03-16 |
| FR2355028A1 (fr) | 1978-01-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| 732 | Registration of transactions, instruments or events in the register (sect. 32/1977) | ||
| PE20 | Patent expired after termination of 20 years |
Effective date: 19960611 |