BE408073A - - Google Patents

Info

Publication number

BE408073A

BE408073A BE408073DA BE408073A BE 408073 A BE408073 A BE 408073A BE 408073D A BE408073D A BE 408073DA BE 408073 A BE408073 A BE 408073A

Authority

BE

Belgium

Prior art keywords

general formula

subjecting

action

group

preparation

Prior art date

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• 239000000047 product Substances 0.000 claims description 26
• 238000000034 method Methods 0.000 claims description 19
• 239000002994 raw material Substances 0.000 claims description 19
• 239000003163 gonadal steroid hormone Substances 0.000 claims description 18
• 125000000468 ketone group Chemical group 0.000 claims description 15
• 150000001875 compounds Chemical class 0.000 claims description 13
• 230000001766 physiological effect Effects 0.000 claims description 12
• 238000002360 preparation method Methods 0.000 claims description 12
• 239000003795 chemical substances by application Substances 0.000 claims description 10
• 239000005556 hormone Substances 0.000 claims description 10
• 229940088597 hormone Drugs 0.000 claims description 10
• 125000003198 secondary alcohol group Chemical group 0.000 claims description 9
• 229930194542 Keto Natural products 0.000 claims description 8
• 125000005594 diketone group Chemical group 0.000 claims description 8
• 239000007800 oxidant agent Substances 0.000 claims description 6
• 238000005984 hydrogenation reaction Methods 0.000 claims description 5
• 239000000463 material Substances 0.000 claims description 5
• 239000007858 starting material Substances 0.000 claims description 5
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
• 239000003054 catalyst Substances 0.000 claims description 4
• -1 dimethyl tetradecahydro phenanthrols Chemical class 0.000 claims description 4
• 230000000694 effects Effects 0.000 claims description 4
• 230000003325 follicular Effects 0.000 claims description 4
• 150000002576 ketones Chemical class 0.000 claims description 4
• 230000003647 oxidation Effects 0.000 claims description 4
• 238000007254 oxidation reaction Methods 0.000 claims description 4
• 239000007795 chemical reaction product Substances 0.000 claims description 3
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
• 238000012986 modification Methods 0.000 claims description 3
• 230000004048 modification Effects 0.000 claims description 3
• 230000015572 biosynthetic process Effects 0.000 claims description 2
• 238000006555 catalytic reaction Methods 0.000 claims description 2
• 150000002431 hydrogen Chemical class 0.000 claims description 2
• 230000007935 neutral effect Effects 0.000 claims description 2
• YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 claims 1
• 239000003929 acidic solution Substances 0.000 claims 1
• 239000012670 alkaline solution Substances 0.000 claims 1
• CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 claims 1
• 150000003333 secondary alcohols Chemical class 0.000 claims 1
• 230000001131 transforming effect Effects 0.000 claims 1
• 239000000243 solution Substances 0.000 description 11
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
• 239000001257 hydrogen Substances 0.000 description 5
• 229910052739 hydrogen Inorganic materials 0.000 description 5
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
• 238000006243 chemical reaction Methods 0.000 description 3
• 230000008018 melting Effects 0.000 description 3
• 238000002844 melting Methods 0.000 description 3
• GTBXZWADMKOZQJ-UHFFFAOYSA-N 1-phenanthrol Chemical compound C1=CC2=CC=CC=C2C2=C1C(O)=CC=C2 GTBXZWADMKOZQJ-UHFFFAOYSA-N 0.000 description 2
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
• 239000002253 acid Substances 0.000 description 2
• 230000001476 alcoholic effect Effects 0.000 description 2
• 150000002009 diols Chemical class 0.000 description 2
• 238000001704 evaporation Methods 0.000 description 2
• 230000008020 evaporation Effects 0.000 description 2
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
• 229910052708 sodium Inorganic materials 0.000 description 2
• 239000011734 sodium Substances 0.000 description 2
• 239000002904 solvent Substances 0.000 description 2
• DYMROBVXGSLPAY-HLUDHZFRSA-N (3s,5s,8r,9s,10r,13s,14s)-3-hydroxy-10,13-dimethyl-3,4,5,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one Chemical compound C1[C@H](O)C=C[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC[C@H]21 DYMROBVXGSLPAY-HLUDHZFRSA-N 0.000 description 1
• QGXBDMJGAMFCBF-HLUDHZFRSA-N 5α-Androsterone Chemical compound C1[C@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC[C@H]21 QGXBDMJGAMFCBF-HLUDHZFRSA-N 0.000 description 1
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
• QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
• 239000005751 Copper oxide Substances 0.000 description 1
• 241000196324 Embryophyta Species 0.000 description 1
• 241001331845 Equus asinus x caballus Species 0.000 description 1
• QGXBDMJGAMFCBF-UHFFFAOYSA-N Etiocholanolone Natural products C1C(O)CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CCC21 QGXBDMJGAMFCBF-UHFFFAOYSA-N 0.000 description 1
• 241001465754 Metazoa Species 0.000 description 1
• 241000332699 Moneses Species 0.000 description 1
• PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
• 229960000583 acetic acid Drugs 0.000 description 1
• 239000003513 alkali Substances 0.000 description 1
• 229910052782 aluminium Inorganic materials 0.000 description 1
• XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
• 229940061641 androsterone Drugs 0.000 description 1
• 239000007864 aqueous solution Substances 0.000 description 1
• 239000004202 carbamide Substances 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
• 229910000431 copper oxide Inorganic materials 0.000 description 1
• 239000000287 crude extract Substances 0.000 description 1
• 239000013078 crystal Substances 0.000 description 1
• 238000002425 crystallisation Methods 0.000 description 1
• 230000008025 crystallization Effects 0.000 description 1
• HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
• 239000012530 fluid Substances 0.000 description 1
• 239000011888 foil Substances 0.000 description 1
• 239000012362 glacial acetic acid Substances 0.000 description 1
• 150000002500 ions Chemical class 0.000 description 1
• 125000005481 linolenic acid group Chemical group 0.000 description 1
• 238000004519 manufacturing process Methods 0.000 description 1
• 229910000474 mercury oxide Inorganic materials 0.000 description 1
• UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 1
• 229910052751 metal Inorganic materials 0.000 description 1
• 239000002184 metal Substances 0.000 description 1
• 125000002320 montanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([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
• 230000003287 optical effect Effects 0.000 description 1
• 210000000056 organ Anatomy 0.000 description 1
• 125000004430 oxygen atom Chemical group O* 0.000 description 1
• 229910052697 platinum Inorganic materials 0.000 description 1
• 238000000746 purification Methods 0.000 description 1
• 238000001953 recrystallisation Methods 0.000 description 1
• 239000000126 substance Substances 0.000 description 1
• 229910052720 vanadium Inorganic materials 0.000 description 1
• 238000005406 washing Methods 0.000 description 1