BE568395A - - Google Patents
Info
- Publication number
- BE568395A BE568395A BE568395DA BE568395A BE 568395 A BE568395 A BE 568395A BE 568395D A BE568395D A BE 568395DA BE 568395 A BE568395 A BE 568395A
- Authority
- BE
- Belgium
- Prior art keywords
- podophyllic
- general formula
- stereoisomeric
- preparation
- raney nickel
- Prior art date
Links
- 239000007868 Raney catalyst Substances 0.000 claims description 7
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 7
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 150000001408 amides Chemical class 0.000 claims description 6
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 claims description 5
- HERDBNDYIUQYJF-UHFFFAOYSA-N [2-hydroxy-3-(2-methylprop-2-enoyloxy)propyl] 2-hydroxybenzoate Chemical compound CC(=C)C(=O)OCC(O)COC(=O)C1=CC=CC=C1O HERDBNDYIUQYJF-UHFFFAOYSA-N 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 2
- 238000005984 hydrogenation reaction Methods 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 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 description 7
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- 230000002927 anti-mitotic effect Effects 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- YJGVMLPVUAXIQN-XVVDYKMHSA-N podophyllotoxin Chemical class 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 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 229960001237 podophyllotoxin Drugs 0.000 description 5
- 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 description 5
- XRBSKUSTLXISAB-XVVDYKMHSA-N (5r,6r,7r,8r)-8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydrobenzo[f][1,3]benzodioxole-6-carboxylic acid Chemical class COC1=C(OC)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@H](O)[C@@H](CO)[C@@H]2C(O)=O)=C1 XRBSKUSTLXISAB-XVVDYKMHSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229930182478 glucoside Natural products 0.000 description 2
- 150000008131 glucosides Chemical class 0.000 description 2
- 231100000086 high toxicity Toxicity 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- YJGVMLPVUAXIQN-HAEOHBJNSA-N picropodophyllotoxin 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-HAEOHBJNSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XRBSKUSTLXISAB-HAEOHBJNSA-N (5r,6s,7r,8r)-8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydrobenzo[f][1,3]benzodioxole-6-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@H](O)[C@@H](CO)[C@H]2C(O)=O)=C1 XRBSKUSTLXISAB-HAEOHBJNSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000010103 Podophyllin Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229940068582 podophyllin Drugs 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE568395A true BE568395A (en, 2012) |
Family
ID=187745
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE568395D BE568395A (en, 2012) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE568395A (en, 2012) |
-
0
- BE BE568395D patent/BE568395A/fr unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1155438A (fr) | Derives d'amino-14 steroides, et procede pour leur preparation | |
| CH652726A5 (fr) | Derives steroides 17-oxazolines, leur procede de preparation et leur utilisation a la preparation de corticosteroides. | |
| FR2689889A1 (fr) | Nouveaux dérivés de perhydroisoindole, et leur préparation. | |
| EP0101383B1 (fr) | Dérivés d'amino-14 stéroides, application en thérapeutique, et procédé de préparation | |
| BE568395A (en, 2012) | ||
| CH316155A (fr) | Procédé de préparation d'un 5-prégnène-17a,21-diol-3,11,20-trione-3,20-dialcoylène-cétal | |
| WO1996038447A1 (fr) | Derives du 2-azabicyclo[2.2.1]heptane, leur preparation et leur application | |
| CH474501A (fr) | Procédé pour la préparation d'un dérivé furannique | |
| FR2792634A1 (fr) | Derives de 2-alcoxy-cyclobutene-3,4-dione leur preparation et leur application en therapeutique | |
| DE69615020T2 (de) | 2-azabicyclo[2.2.1]heptan-derivate, ihre herstellung und ihre anwendung | |
| EP0165225A1 (fr) | Procédé de préparation de l'aza-5 indole et intermédiaires | |
| FR2493850A1 (fr) | Nouveau procede de preparation de derives de triazoloquinazolinone et nouveaux intermediaires obtenus | |
| JPS6130661B2 (en, 2012) | ||
| CH593284A5 (en) | Phthalazino(2,3-b)phthalazine-5,12-dione prepn - from the 5,7,12-trione via 2-(o-carboxybenzyl)1(2H)-phthalazinone | |
| BE572382A (en, 2012) | ||
| CH276049A (fr) | Procédé de préparation d'acide ptéroylglutamique. | |
| BE565010A (en, 2012) | ||
| BE517072A (en, 2012) | ||
| CH610893A5 (en) | Process for the preparation of a 1,5-benzodiazocine derivative | |
| BE570132A (en, 2012) | ||
| BE631748A (en, 2012) | ||
| EP0397567A1 (fr) | Nouvelle substance antitumorale, un procédé de préparation et les compositions pharmaceutiques qui la contiennent | |
| JPS58121260A (ja) | １−アジドシクロプロパンカルボン酸誘導体及びその製造方法 | |
| BE712145A (en, 2012) | ||
| CH592665A5 (en) | 7H-Indolizino (5,6,7-i,j)-isoquinolines - as antibilharzial, anthelmintic and antimicrobial agents |