BE553168A - - Google Patents
Info
- Publication number
- BE553168A BE553168A BE553168DA BE553168A BE 553168 A BE553168 A BE 553168A BE 553168D A BE553168D A BE 553168DA BE 553168 A BE553168 A BE 553168A
- Authority
- BE
- Belgium
- Prior art keywords
- testosterone
- hexahydrobenzoate
- process according
- condensing agent
- reaction
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 1
- NPAGDVCDWIYMMC-IZPLOLCNSA-N nandrolone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 NPAGDVCDWIYMMC-IZPLOLCNSA-N 0.000 description 19
- 229960004719 nandrolone Drugs 0.000 description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 4
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 4
- 238000005119 centrifugation Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- -1 hexahydrobenzoyl halide Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- JOHUAELJNSBTGS-UHFFFAOYSA-N cyclohexanecarbonyl cyclohexanecarboxylate Chemical compound C1CCCCC1C(=O)OC(=O)C1CCCCC1 JOHUAELJNSBTGS-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229960003604 testosterone Drugs 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- VOXZDWNPVJITMN-UHFFFAOYSA-N 13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol Chemical compound OC1=CC=C2C3CCC(C)(C(CC4)O)C4C3CCC2=C1 VOXZDWNPVJITMN-UHFFFAOYSA-N 0.000 description 1
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 206010047486 Virilism Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 238000005899 aromatization reaction Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229960005309 estradiol Drugs 0.000 description 1
- 229930182833 estradiol Natural products 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000003270 steroid hormone Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
Landscapes
- Steroid Compounds (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE553168A true BE553168A (d) |
Family
ID=178083
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE553168D BE553168A (d) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE553168A (d) |
-
0
- BE BE553168D patent/BE553168A/fr unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH624952A5 (d) | ||
| BE553168A (d) | ||
| EP0248736B1 (fr) | Nouveaux dérivés du benzimidazolylthiométhyl benzothiazole substituté et leurs sels, procédé de prépration, application à titre de médicaments et compositions les renfermant | |
| EP0008965B1 (fr) | Nouveaux aminoglycosides dérivés de la désoxystreptamine et leurs sels, leur procédé de préparation, leur application à titre de médicaments et les compositions pharmaceutiques les renfermant | |
| CH529736A (fr) | Nouveau procédé de préparation de dérivés 7a-méthyl stéroïdes | |
| CH442286A (fr) | Procédé de préparation de nouveaux pyrazolostéroïdes | |
| BE440459A (d) | ||
| CH268051A (fr) | Procédé de préparation de 1-méthyl-4-pipérazine-N,N-diéthyl-carboxamide. | |
| CH629223A5 (en) | Process for the preparation of a steroid which is methylated in the 16-alpha position | |
| BE531613A (d) | ||
| BE615024A (d) | ||
| BE633582A (d) | ||
| CH370093A (fr) | Procédé pour la préparation de dérivés de l'acide diamino-caproïque | |
| EP0254611A1 (fr) | Dérivés 8-phénylthiotétrahydroquinoléines substitués et leurs sels, leur préparation à titre de médicaments et les compositions les renfermant | |
| CH388975A (fr) | Procédé de préparation d'un dérivé de la réserpine | |
| CH426858A (fr) | Procédé de préparation de nouveaux dérivés colchiciques | |
| CH368504A (fr) | Procédé de préparation d'une nouvelle lactone contenant du brome | |
| FR2534583A1 (fr) | Procede pour la fabrication d'hexahydro-5-hydroxy-4-hydroxymethyl-2h-cyclopenta-(b)-furanne-2-one | |
| CH337197A (fr) | Procédé de préparation de nouveaux esters d'hormones corticosurrénales | |
| CH404649A (fr) | Procédé de préparation d'un nouveau dérivé colchicique | |
| BE469480A (d) | ||
| BE503510A (d) | ||
| CH368164A (fr) | Procédé pour la préparation de dérivés de l'étiocholane | |
| BE513337A (d) | ||
| BE571750A (d) |