BE554736A - - Google Patents

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Publication number: BE554736A
Authority: BE; Belgium
Prior art keywords: parts; compounds; methyl; carbon atoms; containing less
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Publication of BE554736A publication Critical patent/BE554736A/fr

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150000001875 compounds Chemical class 0.000 claims description 53
LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 49
239000000203 mixture Substances 0.000 claims description 40
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 31
-1 hydrocarbon carboxylic acid Chemical class 0.000 claims description 23
239000011541 reaction mixture Substances 0.000 claims description 21
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 20
WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 18
230000005712 crystallization Effects 0.000 claims description 14
238000000034 method Methods 0.000 claims description 13
239000004215 Carbon black (E152) Substances 0.000 claims description 12
238000002425 crystallisation Methods 0.000 claims description 12
125000004432 carbon atoms Chemical group C* 0.000 claims description 10
239000007858 starting material Substances 0.000 claims description 9
239000005457 ice water Substances 0.000 claims description 8
239000000155 melt Substances 0.000 claims description 8
150000002430 hydrocarbons Chemical class 0.000 claims description 7
150000001735 carboxylic acids Chemical class 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
150000004791 alkyl magnesium halides Chemical class 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
150000003431 steroids Chemical class 0.000 claims description 3
125000002252 acyl group Chemical group 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
150000002009 diols Chemical class 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 claims 1
XXGJRAFLOAKNCC-UHFFFAOYSA-N methane;molecular hydrogen Chemical compound C.[H][H] XXGJRAFLOAKNCC-UHFFFAOYSA-N 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 70
239000000243 solution Substances 0.000 description 68
CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 36
XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
239000000047 product Substances 0.000 description 26
AVFUHBJCUUTGCD-UHFFFAOYSA-M [Br-].[Mg+]C Chemical compound [Br-].[Mg+]C AVFUHBJCUUTGCD-UHFFFAOYSA-M 0.000 description 25
KJDGFQJCHFJTRH-YONAWACDSA-N 16-Ketoestradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](C(=O)C4)O)[C@@H]4[C@@H]3CCC2=C1 KJDGFQJCHFJTRH-YONAWACDSA-N 0.000 description 19
238000006243 chemical reaction Methods 0.000 description 19
235000019441 ethanol Nutrition 0.000 description 16
238000002844 melting Methods 0.000 description 16
238000010992 reflux Methods 0.000 description 16
HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 13
238000001953 recrystallisation Methods 0.000 description 13
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
238000007792 addition Methods 0.000 description 11
239000007795 chemical reaction product Substances 0.000 description 11
235000019270 ammonium chloride Nutrition 0.000 description 10
150000002148 esters Chemical class 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
QDHHCQZDFGDHMP-UHFFFAOYSA-N monochloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 10
230000001076 estrogenic Effects 0.000 description 9
239000002904 solvent Substances 0.000 description 9
HVYWMOMLDIMFJA-DPAQBDIFSA-N Cholesterol Natural products C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
229940088597 Hormone Drugs 0.000 description 8
239000003153 chemical reaction reagent Substances 0.000 description 8
238000001704 evaporation Methods 0.000 description 8
239000005556 hormone Substances 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 7
230000000694 effects Effects 0.000 description 7
150000002170 ethers Chemical class 0.000 description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
239000012074 organic phase Substances 0.000 description 7
125000002524 organometallic group Chemical group 0.000 description 7
238000000926 separation method Methods 0.000 description 7
239000012265 solid product Substances 0.000 description 7
MHAJPDPJQMAIIY-UHFFFAOYSA-N hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
238000006460 hydrolysis reaction Methods 0.000 description 6
FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
239000006227 byproduct Substances 0.000 description 5
239000000262 estrogen Substances 0.000 description 5
239000000463 material Substances 0.000 description 5
239000012299 nitrogen atmosphere Substances 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
239000012047 saturated solution Substances 0.000 description 5
239000000377 silicon dioxide Substances 0.000 description 5
239000007787 solid Substances 0.000 description 5
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 4
235000012000 cholesterol Nutrition 0.000 description 4
230000000875 corresponding Effects 0.000 description 4
230000001264 neutralization Effects 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 4
239000012071 phase Substances 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
DKGAVHZHDRPRBM-UHFFFAOYSA-N t-BuOH Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
229940107161 Cholesterol Drugs 0.000 description 3
229960003399 Estrone Drugs 0.000 description 3
DNXHEGUUPJUMQT-CBZIJGRNSA-N Hiestrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N Methyl iodide Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
206010067572 Oestrogenic effect Diseases 0.000 description 3
210000002966 Serum Anatomy 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
239000012445 acidic reagent Substances 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000012043 crude product Substances 0.000 description 3
238000001035 drying Methods 0.000 description 3
150000002632 lipids Chemical class 0.000 description 3
HPQVWDOOUQVBTO-UHFFFAOYSA-N lithium aluminium hydride Substances [Li+].[Al-] HPQVWDOOUQVBTO-UHFFFAOYSA-N 0.000 description 3
OCZDCIYGECBNKL-UHFFFAOYSA-N lithium;alumanuide Chemical compound [Li+].[AlH4-] OCZDCIYGECBNKL-UHFFFAOYSA-N 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
150000003904 phospholipids Chemical class 0.000 description 3
239000001184 potassium carbonate Substances 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
230000001225 therapeutic Effects 0.000 description 3
238000005406 washing Methods 0.000 description 3
CPBZARXQRZTYGI-UHFFFAOYSA-N 3-cyclopentylpropylcyclohexane Chemical compound C1CCCCC1CCCC1CCCC1 CPBZARXQRZTYGI-UHFFFAOYSA-N 0.000 description 2
GZUXJHMPEANEGY-UHFFFAOYSA-N Bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
RADJLYXZKCROSL-AHQOGOERSA-N C(C)(=O)OC1=CC=2CC[C@H]3[C@@H]4CC(C([C@@]4(C)CC[C@@H]3C2C=C1)OC(C)=O)=O Chemical compound C(C)(=O)OC1=CC=2CC[C@H]3[C@@H]4CC(C([C@@]4(C)CC[C@@H]3C2C=C1)OC(C)=O)=O RADJLYXZKCROSL-AHQOGOERSA-N 0.000 description 2
CASXWAUWPXMGCE-XSYGEPLQSA-N C1C[C@]2(C)C(=O)C(=C)C[C@H]2[C@@H]2CCC3=CC(OC)=CC=C3[C@H]21 Chemical compound C1C[C@]2(C)C(=O)C(=C)C[C@H]2[C@@H]2CCC3=CC(OC)=CC=C3[C@H]21 CASXWAUWPXMGCE-XSYGEPLQSA-N 0.000 description 2
QWOJMRHUQHTCJG-UHFFFAOYSA-N CC([CH2-])=O Chemical compound CC([CH2-])=O QWOJMRHUQHTCJG-UHFFFAOYSA-N 0.000 description 2
229960005309 Estradiol Drugs 0.000 description 2
PROQIPRRNZUXQM-ZXXIGWHRSA-N Estriol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H]([C@H](O)C4)O)[C@@H]4[C@@H]3CCC2=C1 PROQIPRRNZUXQM-ZXXIGWHRSA-N 0.000 description 2
229940011871 Estrogens Drugs 0.000 description 2
PHTQWCKDNZKARW-UHFFFAOYSA-N Isoamyl alcohol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
230000036740 Metabolism Effects 0.000 description 2
WLJVXDMOQOGPHL-UHFFFAOYSA-N Phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
229940067631 Phospholipids Drugs 0.000 description 2
229940030484 SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM ESTROGENS Drugs 0.000 description 2
YQMARKZVVTYGOK-UHFFFAOYSA-M [Br-].CCC[Mg+] Chemical compound [Br-].CCC[Mg+] YQMARKZVVTYGOK-UHFFFAOYSA-M 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000003377 acid catalyst Substances 0.000 description 2
230000000489 anti-atherogenic Effects 0.000 description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
238000010790 dilution Methods 0.000 description 2
IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 2
229940046080 endocrine therapy drugs Estrogens Drugs 0.000 description 2
150000002118 epoxides Chemical class 0.000 description 2
125000004185 ester group Chemical group 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
230000001135 feminizing Effects 0.000 description 2
238000005755 formation reaction Methods 0.000 description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
230000004060 metabolic process Effects 0.000 description 2
230000035786 metabolism Effects 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
150000002902 organometallic compounds Chemical class 0.000 description 2
230000002611 ovarian Effects 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
WCUXLLCKKVVCTQ-UHFFFAOYSA-M potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
230000003389 potentiating Effects 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000000126 substance Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
150000004072 triols Chemical class 0.000 description 2
GNLJBJNONOOOQC-UHFFFAOYSA-N $l^{3}-carbane;magnesium Chemical compound [Mg]C GNLJBJNONOOOQC-UHFFFAOYSA-N 0.000 description 1
OOVXZFCPCSVSEM-NIJQXKJSSA-N (8R,9S,13S,14S)-3-methoxy-13,16-dimethyl-7,8,9,11,12,14,15,17-octahydro-6H-cyclopenta[a]phenanthrene-16,17-diol Chemical compound C1C[C@]2(C)C(O)C(C)(O)C[C@H]2[C@@H]2CCC3=CC(OC)=CC=C3[C@H]21 OOVXZFCPCSVSEM-NIJQXKJSSA-N 0.000 description 1
PYTMPVZFYYVDQO-UIRRPCRCSA-N (9R,10S,13R)-13-methyl-1,2,3,4,5,6,9,10,11,12-decahydrocyclopenta[a]phenanthren-16-ol Chemical compound C([C@@H]12)CCCC1CC=C1[C@@H]2CC[C@@]2(C)C1=CC(O)=C2 PYTMPVZFYYVDQO-UIRRPCRCSA-N 0.000 description 1
DMHZDOTYAVHSEH-UHFFFAOYSA-N 1-(chloromethyl)-4-methylbenzene Chemical compound CC1=CC=C(CCl)C=C1 DMHZDOTYAVHSEH-UHFFFAOYSA-N 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
ZMUTWNYECYKYQF-UHFFFAOYSA-N 3-(2,3-dihydroxyphenyl)butanoic acid Chemical compound OC(=O)CC(C)C1=CC=CC(O)=C1O ZMUTWNYECYKYQF-UHFFFAOYSA-N 0.000 description 1
GAFBGRBPYCNUCH-UHFFFAOYSA-N 4-Methylbenzyl radical Chemical group [CH2]C1=CC=C(C)C=C1 GAFBGRBPYCNUCH-UHFFFAOYSA-N 0.000 description 1
210000001367 Arteries Anatomy 0.000 description 1
HNYOPLTXPVRDBG-UHFFFAOYSA-N Barbituric acid Chemical group O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N Benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N Benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
MFAJVWUMBOQFFK-SKPQLKPYSA-N CC1(C([C@]2(C)[C@@H](C1)[C@@H]1CCC=3C=C(C=CC3[C@H]1CC2)O)O)O Chemical compound CC1(C([C@]2(C)[C@@H](C1)[C@@H]1CCC=3C=C(C=CC3[C@H]1CC2)O)O)O MFAJVWUMBOQFFK-SKPQLKPYSA-N 0.000 description 1
ITKGPLQHPGHFIC-UIBKQYGTSA-N COC1=CC=2CC[C@H]3[C@@H]4CC(C([C@@]4(C)CC[C@@H]3C2C=C1)OC)=O Chemical compound COC1=CC=2CC[C@H]3[C@@H]4CC(C([C@@]4(C)CC[C@@H]3C2C=C1)OC)=O ITKGPLQHPGHFIC-UIBKQYGTSA-N 0.000 description 1
AUPXBVDHVRZMIB-UHFFFAOYSA-M C[Mg]I Chemical compound C[Mg]I AUPXBVDHVRZMIB-UHFFFAOYSA-M 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N Dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
239000004593 Epoxy Substances 0.000 description 1
229960001348 Estriol Drugs 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N Ethyl iodide Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
206010049290 Feminisation acquired Diseases 0.000 description 1
208000009576 Hypercholesterolemia Diseases 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
RQNMYNYHBQQZSP-UHFFFAOYSA-M Methylmagnesium chloride Chemical compound C[Mg]Cl RQNMYNYHBQQZSP-UHFFFAOYSA-M 0.000 description 1
206010053643 Neurodegenerative disease Diseases 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N Potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N Propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
LQHZUFWVUJVYQR-UHFFFAOYSA-M [I-].CCCC[Mg+] Chemical compound [I-].CCCC[Mg+] LQHZUFWVUJVYQR-UHFFFAOYSA-M 0.000 description 1
CDKFWIMBZAUBRS-UHFFFAOYSA-M [I-].CC[Mg+] Chemical compound [I-].CC[Mg+] CDKFWIMBZAUBRS-UHFFFAOYSA-M 0.000 description 1
230000002159 abnormal effect Effects 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
238000007171 acid catalysis Methods 0.000 description 1
230000002378 acidificating Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
230000003042 antagnostic Effects 0.000 description 1
239000012435 aralkylating agent Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
229940073608 benzyl chloride Drugs 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
230000031018 biological processes and functions Effects 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000000271 cardiovascular Effects 0.000 description 1
150000001841 cholesterols Chemical class 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
238000010908 decantation Methods 0.000 description 1
230000018109 developmental process Effects 0.000 description 1
238000007865 diluting Methods 0.000 description 1
LCGLNKUTAGEVQW-UHFFFAOYSA-N dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drugs Drugs 0.000 description 1
230000000534 elicitor Effects 0.000 description 1
238000010828 elution Methods 0.000 description 1
150000002167 estrones Chemical class 0.000 description 1
238000006266 etherification reaction Methods 0.000 description 1
239000002024 ethyl acetate extract Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
BLHLJVCOVBYQQS-UHFFFAOYSA-N ethyllithium Chemical compound [Li]CC BLHLJVCOVBYQQS-UHFFFAOYSA-N 0.000 description 1
230000001747 exhibiting Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000006260 foam Substances 0.000 description 1
WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000003163 gonadal steroid hormone Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000000268 heptanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 1
125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000001794 hormone therapy Methods 0.000 description 1
125000004435 hydrogen atoms Chemical class [H]* 0.000 description 1
230000001077 hypotensive Effects 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
230000003993 interaction Effects 0.000 description 1
238000011031 large scale production Methods 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
UGVPKMAWLOMPRS-UHFFFAOYSA-M magnesium;propane;bromide Chemical compound [Mg+2].[Br-].CC[CH2-] UGVPKMAWLOMPRS-UHFFFAOYSA-M 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
125000006178 methyl benzyl group Chemical group 0.000 description 1
229940102396 methyl bromide Drugs 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000006011 modification reaction Methods 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
229920002866 paraformaldehyde Polymers 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000002035 prolonged Effects 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000003638 reducing agent Substances 0.000 description 1
238000005057 refrigeration Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1

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Steroid Compounds (AREA)

BE554736D BE554736A (pt)

Publications (1)

Publication Number	Publication Date
BE554736A true BE554736A (pt)

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ID=179079

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
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BE (1)	BE554736A (pt)

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- BE BE554736D patent/BE554736A/fr unknown

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