BE685246A - - Google Patents
Info
- Publication number
- BE685246A BE685246A BE685246DA BE685246A BE 685246 A BE685246 A BE 685246A BE 685246D A BE685246D A BE 685246DA BE 685246 A BE685246 A BE 685246A
- Authority
- BE
- Belgium
- Prior art keywords
- acid
- milliliters
- methyl
- ethyl
- animals
- Prior art date
Links
- 239000002253 acid Substances 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 11
- 241001465754 Metazoa Species 0.000 description 8
- 241000700159 Rattus Species 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 235000013305 food Nutrition 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 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 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229930182833 estradiol Natural products 0.000 description 2
- 229960005309 estradiol Drugs 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000001850 reproductive effect Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- HCUOEKSZWPGJIM-YBRHCDHNSA-N (e,2e)-2-hydroxyimino-6-methoxy-4-methyl-5-nitrohex-3-enamide Chemical compound COCC([N+]([O-])=O)\C(C)=C\C(=N/O)\C(N)=O HCUOEKSZWPGJIM-YBRHCDHNSA-N 0.000 description 1
- BFPYWIDHMRZLRN-UHFFFAOYSA-N 17alpha-ethynyl estradiol Natural products OC1=CC=C2C3CCC(C)(C(CC4)(O)C#C)C4C3CCC2=C1 BFPYWIDHMRZLRN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- NMEZJSDUZQOPFE-UHFFFAOYSA-N Cyclohex-1-enecarboxylic acid Chemical class OC(=O)C1=CCCCC1 NMEZJSDUZQOPFE-UHFFFAOYSA-N 0.000 description 1
- BFPYWIDHMRZLRN-SLHNCBLASA-N Ethinyl estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 BFPYWIDHMRZLRN-SLHNCBLASA-N 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010067572 Oestrogenic effect Diseases 0.000 description 1
- 102100030624 Proton myo-inositol cotransporter Human genes 0.000 description 1
- 101710095091 Proton myo-inositol cotransporter Proteins 0.000 description 1
- 239000011717 all-trans-retinol Substances 0.000 description 1
- 235000019169 all-trans-retinol Nutrition 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 210000002808 connective tissue Anatomy 0.000 description 1
- 230000027326 copulation Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000005553 drilling Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229940011871 estrogen Drugs 0.000 description 1
- 239000000262 estrogen Substances 0.000 description 1
- 230000001076 estrogenic effect Effects 0.000 description 1
- 229960002568 ethinylestradiol Drugs 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 235000014571 nuts Nutrition 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000014347 soups Nutrition 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP47683066 | 1966-07-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE685246A true BE685246A (de) | 1967-02-08 |
Family
ID=18527029
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE685246D BE685246A (de) | 1966-07-08 | 1966-08-08 |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE685246A (de) |
-
1966
- 1966-08-08 BE BE685246D patent/BE685246A/fr unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS6033834B2 (ja) | ヘキサヒドロジベンゾピラノン類の製法 | |
| CH632505A5 (fr) | Nouveaux composes a noyau cyclopropanique, procede de preparation et utilisation a la preparation de derives cyclopropaniques a chaine dihalovinylique. | |
| FR2526025A1 (fr) | Analogues des prostaglandines constitues par des 7-oxabicycloheptane hydrazones a action therapeutique | |
| CA1242458A (fr) | Ethers-oxydes et ethers-oximes d'alcoylaminoalcools comme medicaments, produits nouveaux et procedes pour leur preparation | |
| CA1121339A (fr) | PROCEDE DE PREPARATION DE NOUVEAUX DERIVES STEROIDES 11.beta.-SUBSTITUES 1,3,5 (10) TRIENIQUES | |
| DE2434661A1 (de) | Alkoxydibenzo-(b,d)-pyrane, verfahren zu ihrer herstellung und ihre verwendung als arzneistoffe | |
| BE685246A (de) | ||
| FR2744445A1 (fr) | Composes biphenyles nouveaux et/ou a titre de medicament, compositions pharmaceutiques les contenant, leur procede de preparation et les intermediaires de ce procede | |
| MC1156A1 (fr) | Composes cycliques | |
| CA1080242A (fr) | Procede de preparation de la vitamine a a partir de sulfones | |
| EP0135433A1 (de) | Derivate der Benzoesäure zur Anwendung als Arzneimittel und Anwendung dieser Derivate als Konservierungs- oder Desinfektionsmittel | |
| JPS638934B2 (de) | ||
| EP0028959A1 (de) | 5,8,13,13a -Tetrahydro-6H-dibenzo(a,g)chinolizin-Derivate, Verfahren zur Herstellung und sie enthaltende pharmazeutische Zusammensetzungen | |
| CA2018959A1 (fr) | Derives de tetrahydro-5,6,7,8 naphtalenol-1, leur procede de preparation et leur utilisation en tant qu'agents antioxydants dans les compositions cosmetiques et pharmaceutiques les contenant | |
| CA1181411A (fr) | ESTERS D'ALCOOLS .alpha.-HALOGENES, LEUR PROCEDE DE PREPARATION ET LES COMPOSITIONS INSECTICIDES LES RENFERMANT | |
| EP0018245B1 (de) | 7-Alkyl-Steroidderivate, Verfahren zu ihrer Herstellung, ihre Verwendung in Arzneimitteln und pharmazeutische Zusammensetzungen, die sie enthalten | |
| CA1122971A (fr) | PROCEDE DE PREPARATION DE NOUVEAUX DERIVES STEROIDES SUBSTITUES EN 11.beta. | |
| CA2037549A1 (fr) | Utilisation de composes anti-progestomimetiques chez les animaux d'elevage | |
| US4243683A (en) | Tertiary alcohols | |
| DE2461039A1 (de) | Arzneimittel | |
| CA1253859A (fr) | Aryl-10 dihydroxy-1,8 anthrones et leurs esters, et leur procede de preparation | |
| US4103029A (en) | Amino substituted arylthio-alkanoic acids having hypolipidemic activity | |
| BE844350A (fr) | 3-oximes d'esters de d-17a-ethynyl-19-nortestosterone et procede pour les preparer | |
| FR2508907A1 (fr) | Esters d'hydroxybenzenes substitues de 2-thenoylmercaptopropionylglycine utiles notamment comme mucolytiques, procede pour leur preparation et compositions pharmaceutiques les contenant | |
| DE1951990C3 (de) | 3-Cyciopentyloxy-13-äthyl-17alphaäthinylgona-3,5-dien-17beta-ol und dessen Acylderivate |