GB1145909A - The production of 4'-demethyl-epipodophyllotoxin and intermediates therefor - Google Patents
The production of 4'-demethyl-epipodophyllotoxin and intermediates thereforInfo
- Publication number
- GB1145909A GB1145909A GB3289166A GB3289166A GB1145909A GB 1145909 A GB1145909 A GB 1145909A GB 3289166 A GB3289166 A GB 3289166A GB 3289166 A GB3289166 A GB 3289166A GB 1145909 A GB1145909 A GB 1145909A
- Authority
- GB
- United Kingdom
- Prior art keywords
- epipodophyllotoxin
- demethyl
- bromide
- production
- hydrogen
- 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
- FOVRGQUEGRCWPD-UHFFFAOYSA-N (5aR)-9t-beta-D-Glucopyranosyloxy-5t-(4-hydroxy-3,5-dimethoxy-phenyl)-(5ar,8at)-5,8,8a,9-tetrahydro-5aH-furo[3',4';6,7]naphtho[2,3-d][1,3]dioxol-6-on Natural products COC1=C(O)C(OC)=CC(C2C3=CC=4OCOC=4C=C3C(OC3C(C(O)C(O)C(CO)O3)O)C3C2C(OC3)=O)=C1 FOVRGQUEGRCWPD-UHFFFAOYSA-N 0.000 title 1
- YVCVYCSAAZQOJI-JHQYFNNDSA-N 4'-demethylepipodophyllotoxin Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O)[C@@H]3[C@@H]2C(OC3)=O)=C1 YVCVYCSAAZQOJI-JHQYFNNDSA-N 0.000 title 1
- 239000000543 intermediate Substances 0.000 title 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 3
- 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 3
- 229910000042 hydrogen bromide Inorganic materials 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 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 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 210000003855 cell nucleus Anatomy 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 230000002401 inhibitory effect Effects 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
- 230000001225 therapeutic effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/70—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with ring systems containing two or more relevant rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH747068A CH472403A (de) | 1965-09-21 | 1965-09-21 | Verfahren zur Herstellung eines 4'-Demethyl-epipodophyllotoxins |
| CH1301665A CH459255A (de) | 1965-09-21 | 1965-09-21 | Verfahren zur Herstellung von neuen 4'-Demethyl-epipodophyllotoxin-halogeniden |
| CH1301865A CH459257A (de) | 1965-09-21 | 1965-09-21 | Verfahren zur Herstellung von 4'-Demethyl-epipodophyllotoxin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1145909A true GB1145909A (en) | 1969-03-19 |
Family
ID=27175799
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3289166A Expired GB1145909A (en) | 1965-09-21 | 1966-07-21 | The production of 4'-demethyl-epipodophyllotoxin and intermediates therefor |
Country Status (9)
| Country | Link |
|---|---|
| AT (1) | AT281300B (enrdf_load_stackoverflow) |
| BE (1) | BE687089A (enrdf_load_stackoverflow) |
| BR (1) | BR6683006D0 (enrdf_load_stackoverflow) |
| CH (3) | CH459255A (enrdf_load_stackoverflow) |
| FI (1) | FI44411B (enrdf_load_stackoverflow) |
| FR (2) | FR1502813A (enrdf_load_stackoverflow) |
| GB (1) | GB1145909A (enrdf_load_stackoverflow) |
| IL (1) | IL26522A (enrdf_load_stackoverflow) |
| SE (1) | SE327416B (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0119852A1 (en) * | 1983-03-18 | 1984-09-26 | Pharma-medica a-s | Podophyllotoxin preparations for use in the treatment of genital warts |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3043802B2 (ja) * | 1989-02-23 | 2000-05-22 | ザ・ユニバーシティ・オブ・ノース・カロライナ・アット・チャペル・ヒル | エトポシド同族体類 |
| US5463040A (en) * | 1994-06-28 | 1995-10-31 | Teva Pharmaceutical Industries, Ltd. | Method of preparing etoposide |
-
1965
- 1965-09-21 CH CH1301665A patent/CH459255A/de unknown
- 1965-09-21 CH CH747068A patent/CH472403A/de not_active IP Right Cessation
- 1965-09-21 CH CH1301865A patent/CH459257A/de unknown
-
1966
- 1966-07-21 GB GB3289166A patent/GB1145909A/en not_active Expired
- 1966-09-19 FR FR76825A patent/FR1502813A/fr not_active Expired
- 1966-09-19 BE BE687089D patent/BE687089A/xx unknown
- 1966-09-19 IL IL2652266A patent/IL26522A/en unknown
- 1966-09-19 FI FI245566A patent/FI44411B/fi active
- 1966-09-20 SE SE1261866A patent/SE327416B/xx unknown
- 1966-09-20 BR BR18300666A patent/BR6683006D0/pt unknown
- 1966-09-20 AT AT883566A patent/AT281300B/de not_active IP Right Cessation
- 1966-12-16 FR FR87743A patent/FR6307M/fr not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0119852A1 (en) * | 1983-03-18 | 1984-09-26 | Pharma-medica a-s | Podophyllotoxin preparations for use in the treatment of genital warts |
Also Published As
| Publication number | Publication date |
|---|---|
| CH459255A (de) | 1968-07-15 |
| SE327416B (enrdf_load_stackoverflow) | 1970-08-24 |
| FR1502813A (fr) | 1967-11-24 |
| DE1543874A1 (de) | 1970-01-02 |
| CH459257A (de) | 1968-07-15 |
| CH472403A (de) | 1969-05-15 |
| FI44411B (enrdf_load_stackoverflow) | 1971-08-02 |
| BE687089A (enrdf_load_stackoverflow) | 1967-03-20 |
| IL26522A (en) | 1970-06-17 |
| BR6683006D0 (pt) | 1973-12-27 |
| FR6307M (enrdf_load_stackoverflow) | 1968-09-16 |
| AT281300B (de) | 1970-05-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1351263A (en) | Eburnane derivatives | |
| MD225C2 (ro) | Procedeu de obţinere a formei hidratate cristaline a sării de sodiu a acidului 3-acetoximetil-7-12-(2-amino-4-tiazolil)-2-metoxiiminoacetamido-cef-3-em-4-carbonic, sin-izomerului | |
| GB1297398A (enrdf_load_stackoverflow) | ||
| GB1145909A (en) | The production of 4'-demethyl-epipodophyllotoxin and intermediates therefor | |
| GB1434174A (en) | 7-trifluoromethylsulphinylacetamido cephalosporins | |
| GB1171904A (en) | Anilinobenzimidazoles having Antibacterial Properties | |
| GB1292737A (en) | Haloepoxides | |
| ES427115A1 (es) | Procedimiento de preparacion de nuevos derivados del acido acetico. | |
| SE7714304L (sv) | Nya forfaranden for framstellning av 3',4'-dideoxikanamycin b | |
| GB1380734A (en) | Polyene compounds and their manufacture | |
| GB1364392A (en) | Polyisobutylene oxide compositions | |
| ES375401A1 (es) | Procedimiento de preparacion de un nuevo derivado de eri- tromicina soluble en agua. | |
| GB1256995A (enrdf_load_stackoverflow) | ||
| GB1282822A (en) | Butanolamine derivatives | |
| GB1298619A (en) | Thieno benzopyran and thiopyrano benzopyran derivatives and method of making the same | |
| GB1027891A (en) | Esters of dianhydro-hexitols | |
| GB1219700A (en) | Pharmaceutical compositions comprising lincomycin derivatives | |
| GB1434194A (en) | Substituted furenidones and their use as flavouring agents | |
| JPS57185341A (en) | Polybutadiene resin composition | |
| GB1380682A (en) | Aminoisoquinolines | |
| GB1153666A (en) | N-Alkylazaindoles | |
| GB1304633A (enrdf_load_stackoverflow) | ||
| GB1269002A (en) | 0,2,3,4,-tetrahydroisoquinoline derivatives | |
| GB1456955A (en) | Spirotetrahydropyrans and spirothiatetrahydropyrans | |
| IL71407A (en) | 9-deoxo-23-deoxy-9-o-forosaminyl-5-o-mycaminosyltylonolide antibiotics,their preparation and pharmaceutical and veterinary compositions containing them |