BE414067A - - Google Patents

Info

Publication number

BE414067A

BE414067A BE414067DA BE414067A BE 414067 A BE414067 A BE 414067A BE 414067D A BE414067D A BE 414067DA BE 414067 A BE414067 A BE 414067A

Authority

BE

Belgium

Prior art keywords

groups

oxhydryl

ketones

acid

derivatives

Prior art date

Links

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• 239000000047 product Substances 0.000 claims description 20
• 150000003997 cyclic ketones Chemical class 0.000 claims description 12
• 239000007800 oxidant agent Substances 0.000 claims description 10
• WGLPBDUCMAPZCE-UHFFFAOYSA-N trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims description 10
• 239000003795 chemical substances by application Substances 0.000 claims description 9
• 230000001590 oxidative Effects 0.000 claims description 8
• 239000002253 acid Substances 0.000 claims description 7
• 239000003613 bile acid Substances 0.000 claims description 7
• 229910052736 halogen Inorganic materials 0.000 claims description 7
• 150000002576 ketones Chemical class 0.000 claims description 7
• 238000000034 method Methods 0.000 claims description 7
• 150000002367 halogens Chemical class 0.000 claims description 6
• 230000001264 neutralization Effects 0.000 claims description 6
• 210000004940 Nucleus Anatomy 0.000 claims description 5
• 229940117975 chromium trioxide Drugs 0.000 claims description 5
• -1 hydrogen halogen Chemical class 0.000 claims description 5
• 238000006243 chemical reaction Methods 0.000 claims description 4
• 230000001172 regenerating Effects 0.000 claims description 3
• KZJWDPNRJALLNS-VJSFXXLFSA-N β-Sitosterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]1(C)CC2 KZJWDPNRJALLNS-VJSFXXLFSA-N 0.000 claims description 3
• 238000002425 crystallisation Methods 0.000 claims description 2
• 230000005712 crystallization Effects 0.000 claims description 2
• 239000007857 degradation product Substances 0.000 claims description 2
• 238000000746 purification Methods 0.000 claims description 2
• 230000001131 transforming Effects 0.000 claims description 2
• 238000005292 vacuum distillation Methods 0.000 claims description 2
• KZJWDPNRJALLNS-VPUBHVLGSA-N (-)-beta-Sitosterol Natural products O[C@@H]1CC=2[C@@](C)([C@@H]3[C@H]([C@H]4[C@@](C)([C@H]([C@H](CC[C@@H](C(C)C)CC)C)CC4)CC3)CC=2)CC1 KZJWDPNRJALLNS-VPUBHVLGSA-N 0.000 claims 1
• 150000001841 cholesterols Chemical class 0.000 claims 1
• 229910052739 hydrogen Inorganic materials 0.000 claims 1
• 239000001257 hydrogen Substances 0.000 claims 1
• 229950005143 sitosterol Drugs 0.000 claims 1
• 235000015500 sitosterol Nutrition 0.000 claims 1
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
• 229960000583 Acetic Acid Drugs 0.000 description 12
• UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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 Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
• KRVSOGSZCMJSLX-UHFFFAOYSA-L Chromic acid Chemical compound O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 10
• HVYWMOMLDIMFJA-DPAQBDIFSA-N (3β)-Cholest-5-en-3-ol Chemical class 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 9
• VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
• RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
• 239000012362 glacial acetic acid Substances 0.000 description 9
• 239000011780 sodium chloride Substances 0.000 description 9
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 8
• QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
• 230000001476 alcoholic Effects 0.000 description 6
• 238000003756 stirring Methods 0.000 description 6
• CURLTUGMZLYLDI-UHFFFAOYSA-N carbon dioxide Chemical class O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 5
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
• 239000000203 mixture Substances 0.000 description 5
• 238000007127 saponification reaction Methods 0.000 description 5
• 150000007659 semicarbazones Chemical class 0.000 description 5
• VZGDMQKNWNREIO-UHFFFAOYSA-N Carbon tetrachloride Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
• DUIOPKIIICUYRZ-UHFFFAOYSA-N Semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 4
• 150000001875 compounds Chemical class 0.000 description 4
• 239000000155 melt Substances 0.000 description 4
• FMGSKLZLMKYGDP-USOAJAOKSA-N Dehydroepiandrosterone Chemical class C1[C@@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC=C21 FMGSKLZLMKYGDP-USOAJAOKSA-N 0.000 description 3
• 235000011054 acetic acid Nutrition 0.000 description 3
• 150000007513 acids Chemical class 0.000 description 3
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
• WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
• 230000000875 corresponding Effects 0.000 description 3
• 238000001704 evaporation Methods 0.000 description 3
• 238000002844 melting Methods 0.000 description 3
• MUBZPKHOEPUJKR-UHFFFAOYSA-N oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
• XBDQKXXYIPTUBI-UHFFFAOYSA-N propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
• 239000011541 reaction mixture Substances 0.000 description 3
• 238000001953 recrystallisation Methods 0.000 description 3
• HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
• WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
• 229940107161 Cholesterol Drugs 0.000 description 2
• UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
• VZJVWSHVAAUDKD-UHFFFAOYSA-N Potassium permanganate Chemical compound [K+].[O-][Mn](=O)(=O)=O VZJVWSHVAAUDKD-UHFFFAOYSA-N 0.000 description 2
• KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
• CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
• 239000003513 alkali Substances 0.000 description 2
• WPYMKLBDIGXBTP-UHFFFAOYSA-M benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-M 0.000 description 2
• 238000009835 boiling Methods 0.000 description 2
• VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
• 235000012000 cholesterol Nutrition 0.000 description 2
• LCGLNKUTAGEVQW-UHFFFAOYSA-N dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
• 239000003163 gonadal steroid hormone Substances 0.000 description 2
• 238000010438 heat treatment Methods 0.000 description 2
• AVXURJPOCDRRFD-UHFFFAOYSA-N hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
• 150000007524 organic acids Chemical class 0.000 description 2
• 229960002847 prasterone Drugs 0.000 description 2
• 239000002244 precipitate Substances 0.000 description 2
• 238000002360 preparation method Methods 0.000 description 2
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
• 150000003839 salts Chemical class 0.000 description 2
• 239000002904 solvent Substances 0.000 description 2
• YBQZXXMEJHZYMB-UHFFFAOYSA-N 1,2-diphenylhydrazine Chemical compound C=1C=CC=CC=1NNC1=CC=CC=C1 YBQZXXMEJHZYMB-UHFFFAOYSA-N 0.000 description 1
• 239000005711 Benzoic acid Substances 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
• JLTDJTHDQAWBAV-UHFFFAOYSA-N Dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
• 229940093915 Gynecological Organic acids Drugs 0.000 description 1
• LGROKZMEHJZWDU-UHFFFAOYSA-N N-amino-N-phenylnitramide Chemical class [O-][N+](=O)N(N)C1=CC=CC=C1 LGROKZMEHJZWDU-UHFFFAOYSA-N 0.000 description 1
• HKOOXMFOFWEVGF-UHFFFAOYSA-N Phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
• XNGIFLGASWRNHJ-UHFFFAOYSA-N Phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
• WXMKPNITSTVMEF-UHFFFAOYSA-M Sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
• 150000001242 acetic acid derivatives Chemical class 0.000 description 1
• DBJUEJCZPKMDPA-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O DBJUEJCZPKMDPA-UHFFFAOYSA-N 0.000 description 1
• 230000002378 acidificating Effects 0.000 description 1
• 238000007792 addition Methods 0.000 description 1
• 229910052783 alkali metal Inorganic materials 0.000 description 1
• HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical compound NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 description 1
• BRWIZMBXBAOCCF-UHFFFAOYSA-N aminothiourea Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 1
• 239000002585 base Substances 0.000 description 1
• 235000010233 benzoic acid Nutrition 0.000 description 1
• CPELXLSAUQHCOX-UHFFFAOYSA-M bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
• 239000006227 byproduct Substances 0.000 description 1
• KXDHJXZQYSOELW-UHFFFAOYSA-N carbamate Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
• 150000001735 carboxylic acids Chemical class 0.000 description 1
• 239000003610 charcoal Substances 0.000 description 1
• 229910052801 chlorine Inorganic materials 0.000 description 1
• 239000000460 chlorine Substances 0.000 description 1
• ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
• 239000012141 concentrate Substances 0.000 description 1
• 238000000354 decomposition reaction Methods 0.000 description 1
• 150000001991 dicarboxylic acids Chemical class 0.000 description 1
• 238000004821 distillation Methods 0.000 description 1
• 238000005886 esterification reaction Methods 0.000 description 1
• 238000006266 etherification reaction Methods 0.000 description 1
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
• 239000000706 filtrate Substances 0.000 description 1
• CPELXLSAUQHCOX-UHFFFAOYSA-N hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
• 238000006460 hydrolysis reaction Methods 0.000 description 1
• 239000000543 intermediate Substances 0.000 description 1
• 150000004694 iodide salts Chemical class 0.000 description 1
• 230000001788 irregular Effects 0.000 description 1
• 125000000468 ketone group Chemical group 0.000 description 1
• 150000002763 monocarboxylic acids Chemical class 0.000 description 1
• 235000005985 organic acids Nutrition 0.000 description 1
• 235000006408 oxalic acid Nutrition 0.000 description 1
• 230000003647 oxidation Effects 0.000 description 1
• 238000007254 oxidation reaction Methods 0.000 description 1
• NPDODHDPVPPRDJ-UHFFFAOYSA-N permanganate Chemical compound [O-][Mn](=O)(=O)=O NPDODHDPVPPRDJ-UHFFFAOYSA-N 0.000 description 1
• 229940067157 phenylhydrazine Drugs 0.000 description 1
• 235000019260 propionic acid Nutrition 0.000 description 1
• 239000004299 sodium benzoate Substances 0.000 description 1
• 235000010234 sodium benzoate Nutrition 0.000 description 1
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
• 235000017557 sodium bicarbonate Nutrition 0.000 description 1
• 159000000000 sodium salts Chemical class 0.000 description 1
• 238000001256 steam distillation Methods 0.000 description 1
• 239000001384 succinic acid Substances 0.000 description 1
• 238000002560 therapeutic procedure Methods 0.000 description 1