BE540478A

BE540478A -

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Publication number: BE540478A
Authority: BE; Belgium
Prior art keywords: dione; compound; diol; acid; acetate
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English (en)

French (fr)

Publication of BE540478A publication Critical patent/BE540478A/fr

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150000001875 compounds Chemical class 0.000 description 184
238000000034 method Methods 0.000 description 116
229920001098 polystyrene-block-poly(ethylene/propylene) Polymers 0.000 description 112
239000000243 solution Substances 0.000 description 96
150000002148 esters Chemical class 0.000 description 88
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 87
CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 87
HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 70
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 70
238000006243 chemical reaction Methods 0.000 description 69
244000005700 microbiome Species 0.000 description 69
239000007858 starting material Substances 0.000 description 69
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 68
239000002253 acid Substances 0.000 description 66
YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 64
239000000203 mixture Substances 0.000 description 63
LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 60
XOFYZVNMUHMLCC-ZPOLXVRWSA-N Prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 50
239000000047 product Substances 0.000 description 50
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 48
125000002887 hydroxy group Chemical group [H]O* 0.000 description 40
239000000284 extract Substances 0.000 description 38
230000000875 corresponding Effects 0.000 description 37
230000003647 oxidation Effects 0.000 description 37
238000007254 oxidation reaction Methods 0.000 description 37
229960000583 Acetic Acid Drugs 0.000 description 34
150000003431 steroids Chemical class 0.000 description 30
KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 28
OIGNJSKKLXVSLS-VWUMJDOOSA-N Prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 27
MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical group O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 27
-1 steroid compound Chemical class 0.000 description 27
125000002252 acyl group Chemical group 0.000 description 26
235000019441 ethanol Nutrition 0.000 description 26
239000002609 media Substances 0.000 description 25
238000002360 preparation method Methods 0.000 description 25
XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 23
239000000543 intermediate Substances 0.000 description 23
RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
239000011541 reaction mixture Substances 0.000 description 22
238000009835 boiling Methods 0.000 description 21
WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 21
229960000890 hydrocortisone Drugs 0.000 description 21
JYGXADMDTFJGBT-VWUMJDOOSA-N Cortisol Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 20
WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 20
150000001993 dienes Chemical class 0.000 description 20
238000010992 reflux Methods 0.000 description 20
150000007513 acids Chemical class 0.000 description 19
125000004185 ester group Chemical group 0.000 description 19
238000006460 hydrolysis reaction Methods 0.000 description 19
239000007787 solid Substances 0.000 description 19
239000000126 substance Substances 0.000 description 19
229940088597 Hormone Drugs 0.000 description 18
QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 18
239000005556 hormone Substances 0.000 description 18
229910052760 oxygen Inorganic materials 0.000 description 18
239000007795 chemical reaction product Substances 0.000 description 17
230000000694 effects Effects 0.000 description 17
239000001301 oxygen Substances 0.000 description 17
239000002904 solvent Substances 0.000 description 17
238000007792 addition Methods 0.000 description 16
229910052799 carbon Inorganic materials 0.000 description 16
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
229910052739 hydrogen Inorganic materials 0.000 description 16
230000001131 transforming Effects 0.000 description 16
230000000640 hydroxylating Effects 0.000 description 15
QQCBOIWDENXRLP-BYZMTCBYSA-N (8S,9S,10R,13R,14S,17S)-17-ethyl-10,13-dimethyl-6,7,8,9,11,12,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthrene Chemical class C1CC2=CCC=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 QQCBOIWDENXRLP-BYZMTCBYSA-N 0.000 description 14
OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 14
229910052736 halogen Inorganic materials 0.000 description 14
238000001953 recrystallisation Methods 0.000 description 14
MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 description 13
239000003795 chemical substances by application Substances 0.000 description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 13
229960004544 cortisone Drugs 0.000 description 13
230000005712 crystallization Effects 0.000 description 13
150000002576 ketones Chemical class 0.000 description 13
235000015097 nutrients Nutrition 0.000 description 13
239000011780 sodium chloride Substances 0.000 description 13
KRVSOGSZCMJSLX-UHFFFAOYSA-L Chromic acid Chemical compound O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
GEHJYWRUCIMESM-UHFFFAOYSA-L Sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 12
238000002425 crystallisation Methods 0.000 description 12
238000006356 dehydrogenation reaction Methods 0.000 description 12
229910052731 fluorine Inorganic materials 0.000 description 12
150000002367 halogens Chemical class 0.000 description 12
239000001257 hydrogen Substances 0.000 description 12
239000002244 precipitate Substances 0.000 description 12
239000000725 suspension Substances 0.000 description 12
ZESRJSPZRDMNHY-YFWFAHHUSA-N 11-Deoxycorticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 ZESRJSPZRDMNHY-YFWFAHHUSA-N 0.000 description 11
229940041514 Candida albicans extract Drugs 0.000 description 11
UIIMBOGNXHQVGW-UHFFFAOYSA-M buffer Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 11
238000001914 filtration Methods 0.000 description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 11
238000002844 melting Methods 0.000 description 11
239000012138 yeast extract Substances 0.000 description 11
241000223211 Curvularia lunata Species 0.000 description 10
239000002585 base Substances 0.000 description 10
230000015572 biosynthetic process Effects 0.000 description 10
239000003054 catalyst Substances 0.000 description 10
239000012043 crude product Substances 0.000 description 10
235000019439 ethyl acetate Nutrition 0.000 description 10
238000000605 extraction Methods 0.000 description 10
239000008079 hexane Substances 0.000 description 10
238000005805 hydroxylation reaction Methods 0.000 description 10
239000000463 material Substances 0.000 description 10
238000003756 stirring Methods 0.000 description 10
238000000844 transformation Methods 0.000 description 10
TYJJADVDDVDEDZ-UHFFFAOYSA-M Potassium bicarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 9
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
239000001963 growth media Substances 0.000 description 9
230000002906 microbiologic Effects 0.000 description 9
230000004048 modification Effects 0.000 description 9
238000006011 modification reaction Methods 0.000 description 9
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
239000011736 potassium bicarbonate Substances 0.000 description 9
229910000028 potassium bicarbonate Inorganic materials 0.000 description 9
235000015497 potassium bicarbonate Nutrition 0.000 description 9
229940094025 potassium bicarbonate Drugs 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
229940119740 Deoxycorticosterone Drugs 0.000 description 8
108090000790 Enzymes Proteins 0.000 description 8
102000004190 Enzymes Human genes 0.000 description 8
KRHYYFGTRYWZRS-UHFFFAOYSA-N HF Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 8
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-Bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 8
SCVFZCLFOSHCOH-UHFFFAOYSA-M Potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 8
239000000460 chlorine Substances 0.000 description 8
229910052801 chlorine Inorganic materials 0.000 description 8
229960003654 desoxycortone Drugs 0.000 description 8
238000010586 diagram Methods 0.000 description 8
239000012362 glacial acetic acid Substances 0.000 description 8
MHAJPDPJQMAIIY-UHFFFAOYSA-N hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
239000007924 injection Substances 0.000 description 8
125000000468 ketone group Chemical group 0.000 description 8
CSNNHWWHGAXBCP-UHFFFAOYSA-L mgso4 Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
150000003839 salts Chemical class 0.000 description 8
239000008399 tap water Substances 0.000 description 8
235000020679 tap water Nutrition 0.000 description 8
239000004593 Epoxy Substances 0.000 description 7
241000203720 Pimelobacter simplex Species 0.000 description 7
239000003153 chemical reaction reagent Substances 0.000 description 7
VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 7
125000001424 substituent group Chemical group 0.000 description 7
238000003786 synthesis reaction Methods 0.000 description 7
150000008064 anhydrides Chemical class 0.000 description 6
VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
125000001309 chloro group Chemical group Cl* 0.000 description 6
238000007269 dehydrobromination reaction Methods 0.000 description 6
239000003937 drug carrier Substances 0.000 description 6
230000002255 enzymatic Effects 0.000 description 6
238000000855 fermentation Methods 0.000 description 6
230000004151 fermentation Effects 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
CPELXLSAUQHCOX-UHFFFAOYSA-N hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 6
238000002347 injection Methods 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
239000007800 oxidant agent Substances 0.000 description 6
ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
239000000186 progesterone Substances 0.000 description 6
239000012429 reaction media Substances 0.000 description 6
239000001632 sodium acetate Substances 0.000 description 6
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235000010265 sodium sulphite Nutrition 0.000 description 6
239000000758 substrate Substances 0.000 description 6
230000002194 synthesizing Effects 0.000 description 6
150000005671 trienes Chemical class 0.000 description 6
WGLPBDUCMAPZCE-UHFFFAOYSA-N trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 6
SUPOKHOQAKXOHJ-BYZMTCBYSA-N (8S,9S,10R,13R,14S,17S)-17-ethyl-10,13-dimethyl-2,3,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene Chemical compound C1CC2=CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 SUPOKHOQAKXOHJ-BYZMTCBYSA-N 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
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210000004940 Nucleus Anatomy 0.000 description 5
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229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
230000001225 therapeutic Effects 0.000 description 5
CPUKWYXYHPOQJH-RDQPJNLGSA-N (8R,9S,10S,13S,14S)-17-ethenyl-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15-dodecahydro-1H-cyclopenta[a]phenanthrene Chemical compound C1CCC[C@]2(C)[C@H]3CC[C@](C)(C(=CC4)C=C)[C@@H]4[C@@H]3CCC21 CPUKWYXYHPOQJH-RDQPJNLGSA-N 0.000 description 4
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YYROPELSRYBVMQ-UHFFFAOYSA-N 4-Toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
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241000190509 Ophiobolus Species 0.000 description 4
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241000601794 Trichothecium Species 0.000 description 4
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229910052794 bromium Inorganic materials 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
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239000000287 crude extract Substances 0.000 description 4
238000010828 elution Methods 0.000 description 4
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238000001704 evaporation Methods 0.000 description 4
YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
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150000003124 pregnadienes Chemical class 0.000 description 4
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238000006722 reduction reaction Methods 0.000 description 4
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YLFRRPUBVUAHSR-RRPFGEQOSA-N 16,17-didehydropregnenolone Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC=C(C(=O)C)[C@@]1(C)CC2 YLFRRPUBVUAHSR-RRPFGEQOSA-N 0.000 description 3
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AAOMMTQABPVSFY-UHFFFAOYSA-N 5-tert-butylfuran-2-carbonyl chloride Chemical compound CC(C)(C)C1=CC=C(C(Cl)=O)O1 AAOMMTQABPVSFY-UHFFFAOYSA-N 0.000 description 3
PNEYBMLMFCGWSK-UHFFFAOYSA-N AI2O3 Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
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OZWKMVRBQXNZKK-UHFFFAOYSA-N Ketorolac Chemical compound OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1 OZWKMVRBQXNZKK-UHFFFAOYSA-N 0.000 description 3
XCRBXWCUXJNEFX-UHFFFAOYSA-N Peroxybenzoic acid Chemical class OOC(=O)C1=CC=CC=C1 XCRBXWCUXJNEFX-UHFFFAOYSA-N 0.000 description 3
239000007868 Raney catalyst Substances 0.000 description 3
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