ES334425A1 - Procedimiento para la preparacion de epipodofilotoxina - bencilideno - b-d-glucosido. - Google Patents
Procedimiento para la preparacion de epipodofilotoxina - bencilideno - b-d-glucosido.Info
- Publication number
- ES334425A1 ES334425A1 ES334425A ES334425A ES334425A1 ES 334425 A1 ES334425 A1 ES 334425A1 ES 334425 A ES334425 A ES 334425A ES 334425 A ES334425 A ES 334425A ES 334425 A1 ES334425 A1 ES 334425A1
- Authority
- ES
- Spain
- Prior art keywords
- epipodophyllotoxin
- glucoside
- acetyl
- tetra
- compound
- 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
- YJGVMLPVUAXIQN-UHFFFAOYSA-N epipodophyllotoxin Natural products COC1=C(OC)C(OC)=CC(C2C3=CC=4OCOC=4C=C3C(O)C3C2C(OC3)=O)=C1 YJGVMLPVUAXIQN-UHFFFAOYSA-N 0.000 abstract 6
- YJGVMLPVUAXIQN-LGWHJFRWSA-N (5s,5ar,8ar,9r)-5-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5h-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one Chemical compound COC1=C(OC)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O)[C@@H]3[C@@H]2C(OC3)=O)=C1 YJGVMLPVUAXIQN-LGWHJFRWSA-N 0.000 abstract 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- 229930182478 glucoside Natural products 0.000 abstract 3
- 229910015900 BF3 Inorganic materials 0.000 abstract 2
- 239000003377 acid catalyst Substances 0.000 abstract 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Substances FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 2
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 abstract 1
- 238000006136 alcoholysis reaction Methods 0.000 abstract 1
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 abstract 1
- 230000001085 cytostatic effect Effects 0.000 abstract 1
- 229910000474 mercury oxide Inorganic materials 0.000 abstract 1
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 abstract 1
- 238000006140 methanolysis reaction Methods 0.000 abstract 1
- 230000001035 methylating effect Effects 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- YJGVMLPVUAXIQN-XVVDYKMHSA-N podophyllotoxin Chemical compound COC1=C(OC)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@H](O)[C@@H]3[C@@H]2C(OC3)=O)=C1 YJGVMLPVUAXIQN-XVVDYKMHSA-N 0.000 abstract 1
- 229960001237 podophyllotoxin Drugs 0.000 abstract 1
- YVCVYCSAAZQOJI-UHFFFAOYSA-N podophyllotoxin Natural products COC1=C(O)C(OC)=CC(C2C3=CC=4OCOC=4C=C3C(O)C3C2C(OC3)=O)=C1 YVCVYCSAAZQOJI-UHFFFAOYSA-N 0.000 abstract 1
- 239000000829 suppository Substances 0.000 abstract 1
- 150000003751 zinc Chemical class 0.000 abstract 1
- 239000011701 zinc Substances 0.000 abstract 1
- 239000004246 zinc acetate Substances 0.000 abstract 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N zinc oxide Inorganic materials [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
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)
- Medicinal Preparation (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1723165A CH464957A (de) | 1965-12-14 | 1965-12-14 | Verfahren zur Herstellung eines neuen Glucosids |
| CH1362866A CH500183A (de) | 1965-12-14 | 1966-09-21 | Verfahren zur Herstellung eines neuen Glucosides |
| CH1470266 | 1966-10-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES334425A1 true ES334425A1 (es) | 1968-03-16 |
Family
ID=27177026
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES334425A Expired ES334425A1 (es) | 1965-12-14 | 1966-12-12 | Procedimiento para la preparacion de epipodofilotoxina - bencilideno - b-d-glucosido. |
| ES346177A Expired ES346177A1 (es) | 1965-12-14 | 1967-10-18 | Procedimiento para la preparacion de epipodofilotoxina - bencilideno - d-glucosido. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES346177A Expired ES346177A1 (es) | 1965-12-14 | 1967-10-18 | Procedimiento para la preparacion de epipodofilotoxina - bencilideno - d-glucosido. |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3408441A (en, 2012) |
| CH (2) | CH464957A (en, 2012) |
| DE (1) | DE1543891A1 (en, 2012) |
| ES (2) | ES334425A1 (en, 2012) |
| FR (1) | FR6309M (en, 2012) |
| GB (1) | GB1162248A (en, 2012) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LU75760A1 (en, 2012) * | 1976-09-09 | 1978-04-27 | ||
| JPS6032799A (ja) * | 1983-07-29 | 1985-02-19 | Microbial Chem Res Found | 新規４′−デメチル−４−エピポドフィロトキシン誘導体 |
| US4708964A (en) * | 1984-02-09 | 1987-11-24 | Chemex Pharmaceuticals | Lipoxygenase inhibitors |
| US4713246A (en) * | 1984-03-19 | 1987-12-15 | Bristol-Myers Company | Etoposide oral dosage form |
| US4609644A (en) * | 1984-06-15 | 1986-09-02 | St. Jude Children's Research Hospital | Epipodophyllotoxinquinone glucoside derivatives, method of production and use |
| US4916217A (en) * | 1987-01-08 | 1990-04-10 | Bristol-Myers Company | Phosphorus containing derivatives of epipodophyllotoxin |
| US4904768A (en) * | 1987-08-04 | 1990-02-27 | Bristol-Myers Company | Epipodophyllotoxin glucoside 4'-phosphate derivatives |
| US4868291A (en) * | 1987-08-20 | 1989-09-19 | Bristol-Myers Company | 4'-deshydroxyepipodophyllotoxin glucosides: synthesis and use |
| US4888419A (en) * | 1987-08-31 | 1989-12-19 | Bristol-Myers Company | 3'-demethoxyepipodophyllotoxin glucoside derivatives |
| US4935504A (en) * | 1987-12-18 | 1990-06-19 | Bristol-Myers Company | Epipodophyllotoxin glucoside 4'-acyl derivatives |
| US4958010A (en) * | 1988-02-16 | 1990-09-18 | Bristol-Myers Company | Epipodophyllotoxin glucoside lactam derivatives |
| CN1025918C (zh) * | 1990-06-07 | 1994-09-14 | 国家医药管理局上海医药工业研究院 | 抗肿瘤药表鬼臼毒吡喃糖甙的合成新工艺 |
| US6207673B1 (en) | 1997-03-12 | 2001-03-27 | The University Of North Carolina At Chapel Hill | Covalent conjugates of topoisomerase I and topoisomerase II inhibitors |
| CA2343803A1 (en) | 1998-09-10 | 2000-03-23 | Ragina Naidu | Synthetic method for the preparation of the antineoplastic agent etoposide |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2049758A (en) * | 1933-06-03 | 1936-08-04 | Firm H Th Boehme Ag | Process for the production of glucosides of higher aliphatic alcohols |
| US2088792A (en) * | 1933-09-06 | 1937-08-03 | Boehringer & Soehne Gmbh | Sexual hormone compounds and process of producing same |
| US2275969A (en) * | 1936-12-12 | 1942-03-10 | Kongsted August Julius Helmuth | Sterol-like preparation |
| DK126687B (da) * | 1959-01-10 | 1973-08-13 | Ciba Geigy Ag | Analogifremgangsmåde til fremstilling af glucofuranosider eller 2-0-acylderivater deraf. |
| FR1358040A (fr) * | 1963-05-24 | 1964-04-10 | Sandoz Sa | Procédé d'obtention d'un produit nouveau à partir de podophyllum |
| US3296245A (en) * | 1965-03-11 | 1967-01-03 | Olin Mathieson | Process for the preparation of methylalpha-d-glucoside |
-
1965
- 1965-12-14 CH CH1723165A patent/CH464957A/de unknown
-
1966
- 1966-09-21 CH CH1362866A patent/CH500183A/de not_active IP Right Cessation
- 1966-11-25 GB GB53003/66A patent/GB1162248A/en not_active Expired
- 1966-12-10 DE DE19661543891 patent/DE1543891A1/de active Pending
- 1966-12-12 US US600718A patent/US3408441A/en not_active Expired - Lifetime
- 1966-12-12 ES ES334425A patent/ES334425A1/es not_active Expired
-
1967
- 1967-03-10 FR FR98339A patent/FR6309M/fr not_active Expired
- 1967-10-18 ES ES346177A patent/ES346177A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US3408441A (en) | 1968-10-29 |
| CH464957A (de) | 1968-11-15 |
| GB1162248A (en) | 1969-08-20 |
| ES346177A1 (es) | 1969-04-16 |
| CH500183A (de) | 1970-12-15 |
| DE1543891A1 (de) | 1970-02-12 |
| FR6309M (en, 2012) | 1968-09-16 |
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