BE407200A - - Google Patents

Info

Publication number

BE407200A

BE407200A BE407200DA BE407200A BE 407200 A BE407200 A BE 407200A BE 407200D A BE407200D A BE 407200DA BE 407200 A BE407200 A BE 407200A

Authority

BE

Belgium

Prior art keywords

acid

oxidation

pregnanolones

desc

separation

Prior art date

Links

• Espacenet
• Global Dossier
• Discuss

• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
• 230000003647 oxidation Effects 0.000 claims description 10
• 238000007254 oxidation reaction Methods 0.000 claims description 10
• 239000002253 acid Substances 0.000 claims description 9
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
• 229930182558 Sterol Natural products 0.000 claims description 5
• 230000001476 alcoholic effect Effects 0.000 claims description 5
• 150000003432 sterols Chemical class 0.000 claims description 5
• 235000003702 sterols Nutrition 0.000 claims description 5
• 238000000034 method Methods 0.000 claims description 4
• 238000002360 preparation method Methods 0.000 claims description 4
• KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 claims description 3
• 238000003776 cleavage reaction Methods 0.000 claims description 3
• 238000002425 crystallisation Methods 0.000 claims description 3
• 230000008025 crystallization Effects 0.000 claims description 3
• AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 claims description 3
• 239000000203 mixture Substances 0.000 claims description 3
• 239000007800 oxidant agent Substances 0.000 claims description 3
• 239000002994 raw material Substances 0.000 claims description 3
• 230000007017 scission Effects 0.000 claims description 3
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 2
• 230000000903 blocking effect Effects 0.000 claims description 2
• 230000015556 catabolic process Effects 0.000 claims description 2
• 238000006731 degradation reaction Methods 0.000 claims description 2
• 238000000926 separation method Methods 0.000 claims 2
• 230000009089 cytolysis Effects 0.000 claims 1
• 235000019441 ethanol Nutrition 0.000 claims 1
• ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims 1
• 238000002955 isolation Methods 0.000 claims 1
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
• 239000000243 solution Substances 0.000 description 9
• QYIXCDOBOSTCEI-QCYZZNICSA-N (5alpha)-cholestan-3beta-ol Chemical compound C([C@@H]1CC2)[C@@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CCCC(C)C)[C@@]2(C)CC1 QYIXCDOBOSTCEI-QCYZZNICSA-N 0.000 description 7
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 7
• QYIXCDOBOSTCEI-UHFFFAOYSA-N alpha-cholestanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 QYIXCDOBOSTCEI-UHFFFAOYSA-N 0.000 description 7
• FGKJLKRYENPLQH-UHFFFAOYSA-N isocaproic acid Chemical compound CC(C)CCC(O)=O FGKJLKRYENPLQH-UHFFFAOYSA-N 0.000 description 7
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
• 150000002576 ketones Chemical class 0.000 description 6
• AURFZBICLPNKBZ-UHFFFAOYSA-N Pregnanolone Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(=O)C)C1(C)CC2 AURFZBICLPNKBZ-UHFFFAOYSA-N 0.000 description 5
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
• AURFZBICLPNKBZ-FZCSVUEKSA-N 3beta-hydroxy-5alpha-pregnan-20-one Chemical compound C([C@@H]1CC2)[C@@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)C)[C@@]2(C)CC1 AURFZBICLPNKBZ-FZCSVUEKSA-N 0.000 description 4
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
• WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 4
• 150000007513 acids Chemical class 0.000 description 4
• 239000007788 liquid Substances 0.000 description 4
• 230000007935 neutral effect Effects 0.000 description 4
• RHLVCLIPMVJYKS-UHFFFAOYSA-N 3-octanone Chemical compound CCCCCC(=O)CC RHLVCLIPMVJYKS-UHFFFAOYSA-N 0.000 description 3
• 229910000029 sodium carbonate Inorganic materials 0.000 description 3
• 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 2
• QGXBDMJGAMFCBF-UHFFFAOYSA-N Etiocholanolone Natural products C1C(O)CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CCC21 QGXBDMJGAMFCBF-UHFFFAOYSA-N 0.000 description 2
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
• 150000001299 aldehydes Chemical class 0.000 description 2
• 229940061641 androsterone Drugs 0.000 description 2
• 239000007864 aqueous solution Substances 0.000 description 2
• 125000004432 carbon atom Chemical group C* 0.000 description 2
• 238000000354 decomposition reaction Methods 0.000 description 2
• 238000004821 distillation Methods 0.000 description 2
• 150000002170 ethers Chemical class 0.000 description 2
• 229940088597 hormone Drugs 0.000 description 2
• 239000005556 hormone Substances 0.000 description 2
• 238000002844 melting Methods 0.000 description 2
• 230000008018 melting Effects 0.000 description 2
• 239000012452 mother liquor Substances 0.000 description 2
• 238000007127 saponification reaction Methods 0.000 description 2
• 150000007659 semicarbazones Chemical class 0.000 description 2
• 239000000126 substance Substances 0.000 description 2
• VGSSUFQMXBFFTM-UHFFFAOYSA-N (24R)-24-ethyl-5alpha-cholestane-3beta,5,6beta-triol Natural products C1C(O)C2(O)CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 VGSSUFQMXBFFTM-UHFFFAOYSA-N 0.000 description 1
• XIIAYQZJNBULGD-UHFFFAOYSA-N (5alpha)-cholestane Natural products C1CC2CCCCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 XIIAYQZJNBULGD-UHFFFAOYSA-N 0.000 description 1
• TYRGTHQUZVMKOF-UHFFFAOYSA-N 16,17-dihydro-15h-cyclopenta[a]phenanthrene Chemical compound C1=CC=C2C3=CC=C4CCCC4=C3C=CC2=C1 TYRGTHQUZVMKOF-UHFFFAOYSA-N 0.000 description 1
• YSULOORXQBDPCU-UHFFFAOYSA-N 2-(trimethylazaniumyl)ethanehydrazonate;hydrochloride Chemical compound [Cl-].C[N+](C)(C)CC(=O)NN YSULOORXQBDPCU-UHFFFAOYSA-N 0.000 description 1
• QGXBDMJGAMFCBF-BNSUEQOYSA-N 3alpha-hydroxy-5beta-androstan-17-one 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-BNSUEQOYSA-N 0.000 description 1
• AURFZBICLPNKBZ-YZRLXODZSA-N 3alpha-hydroxy-5beta-pregnan-20-one Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)C)[C@@]2(C)CC1 AURFZBICLPNKBZ-YZRLXODZSA-N 0.000 description 1
• PHLIUSDPFOUISN-UHFFFAOYSA-N 3beta-cholestanyl acetate Natural products C1CC2CC(OC(C)=O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 PHLIUSDPFOUISN-UHFFFAOYSA-N 0.000 description 1
• AURFZBICLPNKBZ-GRWISUQFSA-N 3beta-hydroxy-5beta-pregnan-20-one Chemical compound C([C@H]1CC2)[C@@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)C)[C@@]2(C)CC1 AURFZBICLPNKBZ-GRWISUQFSA-N 0.000 description 1
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
• VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
• QYIXCDOBOSTCEI-KKFSNPNRSA-N Epi-coprostanol Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CCCC(C)C)[C@@]2(C)CC1 QYIXCDOBOSTCEI-KKFSNPNRSA-N 0.000 description 1
• LGJMUZUPVCAVPU-JFBKYFIKSA-N Sitostanol Natural products O[C@@H]1C[C@H]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)CC2)CC1 LGJMUZUPVCAVPU-JFBKYFIKSA-N 0.000 description 1
• 150000001242 acetic acid derivatives Chemical class 0.000 description 1
• 239000000061 acid fraction Substances 0.000 description 1
• 238000013019 agitation Methods 0.000 description 1
• 125000003158 alcohol group Chemical group 0.000 description 1
• 125000001931 aliphatic group Chemical group 0.000 description 1
• 150000008064 anhydrides Chemical class 0.000 description 1
• LGJMUZUPVCAVPU-UHFFFAOYSA-N beta-Sitostanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 LGJMUZUPVCAVPU-UHFFFAOYSA-N 0.000 description 1
• 230000015572 biosynthetic process Effects 0.000 description 1
• 238000009835 boiling Methods 0.000 description 1
• XIIAYQZJNBULGD-LDHZKLTISA-N cholestane Chemical compound C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 XIIAYQZJNBULGD-LDHZKLTISA-N 0.000 description 1
• 229910052804 chromium Inorganic materials 0.000 description 1
• 239000011651 chromium Substances 0.000 description 1
• WYYQVWLEPYFFLP-UHFFFAOYSA-K chromium(3+);triacetate Chemical compound [Cr+3].CC([O-])=O.CC([O-])=O.CC([O-])=O WYYQVWLEPYFFLP-UHFFFAOYSA-K 0.000 description 1
• 238000001816 cooling Methods 0.000 description 1
• 239000012043 crude product Substances 0.000 description 1
• 230000000593 degrading effect Effects 0.000 description 1
• PVBMWIXRKLGXPI-UHFFFAOYSA-N dichloro-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)-methylsilane Chemical compound C[Si](Cl)(Cl)CCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F PVBMWIXRKLGXPI-UHFFFAOYSA-N 0.000 description 1
• 229950007402 eltanolone Drugs 0.000 description 1
• 239000000839 emulsion Substances 0.000 description 1
• 235000019439 ethyl acetate Nutrition 0.000 description 1
• 238000001704 evaporation Methods 0.000 description 1
• 230000008020 evaporation Effects 0.000 description 1
• 230000001747 exhibiting effect Effects 0.000 description 1
• 238000000605 extraction Methods 0.000 description 1
• 238000007429 general method Methods 0.000 description 1
• 150000007857 hydrazones Chemical class 0.000 description 1
• 229910052500 inorganic mineral Inorganic materials 0.000 description 1
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
• 239000011707 mineral Substances 0.000 description 1
• 238000006386 neutralization reaction Methods 0.000 description 1
• 230000003287 optical effect Effects 0.000 description 1
• 230000001590 oxidative effect Effects 0.000 description 1
• 150000002923 oximes Chemical class 0.000 description 1
• 239000000047 product Substances 0.000 description 1
• 239000011541 reaction mixture Substances 0.000 description 1
• 238000011084 recovery Methods 0.000 description 1
• 238000010992 reflux Methods 0.000 description 1
• 239000002904 solvent Substances 0.000 description 1
• LGJMUZUPVCAVPU-HRJGVYIJSA-N stigmastanol Chemical compound C([C@@H]1CC2)[C@@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]2(C)CC1 LGJMUZUPVCAVPU-HRJGVYIJSA-N 0.000 description 1
• 238000003756 stirring Methods 0.000 description 1
• 238000003786 synthesis reaction Methods 0.000 description 1
• 238000005303 weighing Methods 0.000 description 1