DD213242A5 - Verfahren zur umwandlung von 1,2-gesaettigten steroiden in 1,2-dehydrosteroide - Google Patents
Verfahren zur umwandlung von 1,2-gesaettigten steroiden in 1,2-dehydrosteroide Download PDFInfo
- Publication number
- DD213242A5 DD213242A5 DD25312383A DD25312383A DD213242A5 DD 213242 A5 DD213242 A5 DD 213242A5 DD 25312383 A DD25312383 A DD 25312383A DD 25312383 A DD25312383 A DD 25312383A DD 213242 A5 DD213242 A5 DD 213242A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- dione
- pregn
- steroid
- methyl
- acetoxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 34
- 150000003431 steroids Chemical class 0.000 title claims description 72
- 238000006243 chemical reaction Methods 0.000 claims abstract description 40
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 12
- 239000003960 organic solvent Substances 0.000 claims abstract description 10
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 36
- MJVAVZPDRWSRRC-UHFFFAOYSA-N Menadione Chemical compound C1=CC=C2C(=O)C(C)=CC(=O)C2=C1 MJVAVZPDRWSRRC-UHFFFAOYSA-N 0.000 claims description 30
- 239000000758 substrate Substances 0.000 claims description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- 235000012711 vitamin K3 Nutrition 0.000 claims description 13
- 239000011652 vitamin K3 Substances 0.000 claims description 13
- 229940041603 vitamin k 3 Drugs 0.000 claims description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 11
- 241000894006 Bacteria Species 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 claims description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 6
- 108091006149 Electron carriers Proteins 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 239000008096 xylene Substances 0.000 claims description 4
- 238000002485 combustion reaction Methods 0.000 claims description 3
- WIXFIQKTHUVFDI-UHFFFAOYSA-N menadione sulfonic acid Chemical compound C1=CC=C2C(=O)C(C)(S(O)(=O)=O)CC(=O)C2=C1 WIXFIQKTHUVFDI-UHFFFAOYSA-N 0.000 claims description 3
- 238000004090 dissolution Methods 0.000 claims description 2
- 229930003448 Vitamin K Natural products 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 238000007865 diluting Methods 0.000 claims 1
- SHUZOJHMOBOZST-UHFFFAOYSA-N phylloquinone Natural products CC(C)CCCCC(C)CCC(C)CCCC(=CCC1=C(C)C(=O)c2ccccc2C1=O)C SHUZOJHMOBOZST-UHFFFAOYSA-N 0.000 claims 1
- 235000019168 vitamin K Nutrition 0.000 claims 1
- 239000011712 vitamin K Substances 0.000 claims 1
- 150000003721 vitamin K derivatives Chemical class 0.000 claims 1
- 229940046010 vitamin k Drugs 0.000 claims 1
- 244000005700 microbiome Species 0.000 abstract description 16
- 230000000694 effects Effects 0.000 abstract description 8
- 108010001070 3-oxosteroid delta(1) dehydrogenase Proteins 0.000 abstract description 7
- 238000002360 preparation method Methods 0.000 abstract description 7
- 230000000813 microbial effect Effects 0.000 abstract description 4
- 230000002906 microbiologic effect Effects 0.000 abstract description 2
- 210000004027 cell Anatomy 0.000 description 51
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 241000430521 Alyssum Species 0.000 description 14
- 239000000203 mixture Substances 0.000 description 12
- 238000006356 dehydrogenation reaction Methods 0.000 description 10
- 238000011534 incubation Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000000855 fermentation Methods 0.000 description 8
- 230000004151 fermentation Effects 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 108090000790 Enzymes Proteins 0.000 description 7
- 102000004190 Enzymes Human genes 0.000 description 7
- JYGXADMDTFJGBT-VWUMJDOOSA-N Hydrocortisone Natural products 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 7
- 239000000370 acceptor Substances 0.000 description 7
- HJTUINCBGMVXOB-LNMJFAINSA-N Androsta-4,9(11)-diene-3,17-dione Chemical compound O=C1CC[C@]2(C)C3=CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 HJTUINCBGMVXOB-LNMJFAINSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- AEMFNILZOJDQLW-QAGGRKNESA-N androst-4-ene-3,17-dione Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 AEMFNILZOJDQLW-QAGGRKNESA-N 0.000 description 6
- 239000003246 corticosteroid Substances 0.000 description 6
- OSVMTWJCGUFAOD-KZQROQTASA-N formestane Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1O OSVMTWJCGUFAOD-KZQROQTASA-N 0.000 description 6
- 241000187654 Nocardia Species 0.000 description 5
- 241000203720 Pimelobacter simplex Species 0.000 description 5
- 239000000872 buffer Substances 0.000 description 5
- 229960001334 corticosteroids Drugs 0.000 description 5
- 229960000890 hydrocortisone Drugs 0.000 description 5
- -1 prednisone steroids Chemical class 0.000 description 5
- ITRJWOMZKQRYTA-RFZYENFJSA-N Cortisone acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)C)(O)[C@@]1(C)CC2=O ITRJWOMZKQRYTA-RFZYENFJSA-N 0.000 description 4
- 241000186216 Corynebacterium Species 0.000 description 4
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 4
- 235000010633 broth Nutrition 0.000 description 4
- 229960003290 cortisone acetate Drugs 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000008103 glucose Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 235000015097 nutrients Nutrition 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 230000009466 transformation Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241000186063 Arthrobacter Species 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 240000008042 Zea mays Species 0.000 description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 235000005822 corn Nutrition 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000008363 phosphate buffer Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- LUJVUUWNAPIQQI-UHFFFAOYSA-N (+)-androsta-1,4-diene-3,17-dione Natural products O=C1C=CC2(C)C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 LUJVUUWNAPIQQI-UHFFFAOYSA-N 0.000 description 2
- CGEGFONWORJNTM-LTGMLJBUSA-N (6s,8s,10r,13s,14s)-6,10,13-trimethyl-2,6,7,8,12,14,15,16-octahydro-1h-cyclopenta[a]phenanthrene-3,17-dione Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1C2=CC[C@]2(C)C(=O)CC[C@H]21 CGEGFONWORJNTM-LTGMLJBUSA-N 0.000 description 2
- KDVNGRJNGNAPSO-LTGMLJBUSA-N (6s,8s,10r,13s,14s)-6,10,13-trimethyl-7,8,12,14,15,16-hexahydro-6h-cyclopenta[a]phenanthrene-3,17-dione Chemical compound C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1C2=CC[C@]2(C)C(=O)CC[C@H]21 KDVNGRJNGNAPSO-LTGMLJBUSA-N 0.000 description 2
- LOTXLBRAMLYOOM-DTIMJLODSA-N (6s,8s,10r,13s,14s)-6-fluoro-10,13-dimethyl-2,6,7,8,12,14,15,16-octahydro-1h-cyclopenta[a]phenanthrene-3,17-dione Chemical compound O=C1CC[C@]2(C)C3=CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3C[C@H](F)C2=C1 LOTXLBRAMLYOOM-DTIMJLODSA-N 0.000 description 2
- NFDIJBXBFYAZJI-DTIMJLODSA-N (6s,8s,10r,13s,14s)-6-fluoro-10,13-dimethyl-7,8,12,14,15,16-hexahydro-6h-cyclopenta[a]phenanthrene-3,17-dione Chemical compound O=C1C=C[C@]2(C)C3=CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3C[C@H](F)C2=C1 NFDIJBXBFYAZJI-DTIMJLODSA-N 0.000 description 2
- NNPWVPDIRNJLIN-LNMJFAINSA-N (8s,10s,13s,14s)-10,13-dimethyl-7,8,12,14,15,16-hexahydro-6h-cyclopenta[a]phenanthrene-3,17-dione Chemical compound O=C1C=C[C@]2(C)C3=CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 NNPWVPDIRNJLIN-LNMJFAINSA-N 0.000 description 2
- MATJXMUQVASJHW-ONKRVSLGSA-N (8s,10s,13s,14s,17r)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-7,8,12,14,15,16-hexahydro-6h-cyclopenta[a]phenanthren-3-one Chemical compound O=C1C=C[C@]2(C)C3=CC[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MATJXMUQVASJHW-ONKRVSLGSA-N 0.000 description 2
- SXNYYEPTQTZOHG-UHFFFAOYSA-N 1,8-diazacyclotetradecane-2,7-dione Chemical compound O=C1CCCCC(=O)NCCCCCCN1 SXNYYEPTQTZOHG-UHFFFAOYSA-N 0.000 description 2
- FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Chemical group O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 description 2
- SXDJNTFEKRMWCP-PPMYUTJDSA-N 2-[(8s,9s,10r,11s,13s,14s)-11-hydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthren-17-ylidene]ethyl acetate Chemical class C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CCC(=CCOC(=O)C)[C@@]1(C)C[C@@H]2O SXDJNTFEKRMWCP-PPMYUTJDSA-N 0.000 description 2
- RXGJTUSBYWCRBK-UHFFFAOYSA-M 5-methylphenazinium methyl sulfate Chemical compound COS([O-])(=O)=O.C1=CC=C2[N+](C)=C(C=CC=C3)C3=NC2=C1 RXGJTUSBYWCRBK-UHFFFAOYSA-M 0.000 description 2
- YUWPMEXLKGOSBF-GACAOOTBSA-N Anecortave acetate Chemical compound O=C1CC[C@]2(C)C3=CC[C@]4(C)[C@](C(=O)COC(=O)C)(O)CC[C@H]4[C@@H]3CCC2=C1 YUWPMEXLKGOSBF-GACAOOTBSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical group 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 2
- MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Chemical group O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- 239000001888 Peptone Substances 0.000 description 2
- 108010080698 Peptones Proteins 0.000 description 2
- SNMKPDYDNGYYEM-NZDAKWCRSA-N [2-[(8s,10s,13s,14s,16s,17r)-17-hydroxy-10,13,16-trimethyl-3-oxo-2,6,7,8,12,14,15,16-octahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate Chemical compound C([C@H]12)CC3=CC(=O)CC[C@]3(C)C1=CC[C@@]1(C)[C@H]2C[C@H](C)[C@]1(O)C(=O)COC(C)=O SNMKPDYDNGYYEM-NZDAKWCRSA-N 0.000 description 2
- KYCCZIHTLYZNFV-SCKJBXJSSA-N [2-[(8s,10s,13s,14s,16s,17r)-17-hydroxy-10,13,16-trimethyl-3-oxo-2,6,7,8,12,14,15,16-octahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] benzoate Chemical compound O=C([C@]1(O)[C@@]2(C)CC=C3[C@@]4(C)CCC(=O)C=C4CC[C@H]3[C@@H]2C[C@@H]1C)COC(=O)C1=CC=CC=C1 KYCCZIHTLYZNFV-SCKJBXJSSA-N 0.000 description 2
- LUJVUUWNAPIQQI-QAGGRKNESA-N androsta-1,4-diene-3,17-dione Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 LUJVUUWNAPIQQI-QAGGRKNESA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 235000015241 bacon Nutrition 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000006285 cell suspension Substances 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol 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)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- ACTIUHUUMQJHFO-UPTCCGCDSA-N coenzyme Q10 Chemical compound COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UPTCCGCDSA-N 0.000 description 2
- 235000017471 coenzyme Q10 Nutrition 0.000 description 2
- 229960004544 cortisone Drugs 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000002360 explosive Substances 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000003100 immobilizing effect Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- 229960004584 methylprednisolone Drugs 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 235000019319 peptone Nutrition 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 229960005205 prednisolone Drugs 0.000 description 2
- 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 2
- 239000002002 slurry Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000000844 transformation Methods 0.000 description 2
- 229940088594 vitamin Drugs 0.000 description 2
- 235000013343 vitamin Nutrition 0.000 description 2
- 239000011782 vitamin Substances 0.000 description 2
- 229930003231 vitamin Natural products 0.000 description 2
- 150000003722 vitamin derivatives Chemical class 0.000 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 description 1
- CSVWWLUMXNHWSU-UHFFFAOYSA-N (22E)-(24xi)-24-ethyl-5alpha-cholest-22-en-3beta-ol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(CC)C(C)C)C1(C)CC2 CSVWWLUMXNHWSU-UHFFFAOYSA-N 0.000 description 1
- OILXMJHPFNGGTO-UHFFFAOYSA-N (22E)-(24xi)-24-methylcholesta-5,22-dien-3beta-ol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(C)C(C)C)C1(C)CC2 OILXMJHPFNGGTO-UHFFFAOYSA-N 0.000 description 1
- UXRVRLDXIBQCQI-CCASCXMYSA-N (6s,8s,9s,10r,11s,13s,14s)-11-hydroxy-6,10,13-trimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthrene-3,17-dione Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)C(=O)CC[C@H]21 UXRVRLDXIBQCQI-CCASCXMYSA-N 0.000 description 1
- TVJLVPVXJZGLPJ-CCASCXMYSA-N (6s,8s,9s,10r,11s,13s,14s)-11-hydroxy-6,10,13-trimethyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthrene-3,17-dione Chemical compound C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)C(=O)CC[C@H]21 TVJLVPVXJZGLPJ-CCASCXMYSA-N 0.000 description 1
- JQVUIHNKYYECGH-CEGNMAFCSA-N (8r,9s,10r,13s,14s,17r)-17-acetyl-17-hydroxy-10,13-dimethyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthren-3-one Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)C)(O)[C@@]1(C)CC2 JQVUIHNKYYECGH-CEGNMAFCSA-N 0.000 description 1
- ZHOLUHXKCIXGSR-KCZNZURUSA-N (8s,9s,10r,11s,13s,14s)-11-hydroxy-10,13-dimethyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthrene-3,17-dione Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 ZHOLUHXKCIXGSR-KCZNZURUSA-N 0.000 description 1
- RZACPWSZIQKVDY-IRIMSJTPSA-N (8s,9s,10r,13s,14s)-10,13-dimethyl-6,7,8,9,12,14,15,16-octahydrocyclopenta[a]phenanthrene-3,11,17-trione Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 RZACPWSZIQKVDY-IRIMSJTPSA-N 0.000 description 1
- ZHOLUHXKCIXGSR-GBHAUCNQSA-N 11alpha-Hydroxyandrosta-1,4-diene-3,17-dione Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@H](O)C[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 ZHOLUHXKCIXGSR-GBHAUCNQSA-N 0.000 description 1
- WSCUHXPGYUMQEX-GBHAUCNQSA-N 11b-Hydroxyandrost-4-ene-3,17-dione Chemical compound O=C1CC[C@]2(C)[C@H]3[C@H](O)C[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 WSCUHXPGYUMQEX-GBHAUCNQSA-N 0.000 description 1
- DBPWSSGDRRHUNT-UHFFFAOYSA-N 17alpha-hydroxy progesterone Natural products C1CC2=CC(=O)CCC2(C)C2C1C1CCC(C(=O)C)(O)C1(C)CC2 DBPWSSGDRRHUNT-UHFFFAOYSA-N 0.000 description 1
- DBPWSSGDRRHUNT-CEGNMAFCSA-N 17α-hydroxyprogesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)C)(O)[C@@]1(C)CC2 DBPWSSGDRRHUNT-CEGNMAFCSA-N 0.000 description 1
- SUFJHQFIKDZJAJ-PPMYUTJDSA-N 2-[(8s,9s,10r,11s,13s,14s)-11-hydroxy-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-17-ylidene]ethyl acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CCC(=CCOC(=O)C)[C@@]1(C)C[C@@H]2O SUFJHQFIKDZJAJ-PPMYUTJDSA-N 0.000 description 1
- KLEXDBGYSOIREE-UHFFFAOYSA-N 24xi-n-propylcholesterol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CCC)C(C)C)C1(C)CC2 KLEXDBGYSOIREE-UHFFFAOYSA-N 0.000 description 1
- VHRSUDSXCMQTMA-PJHHCJLFSA-N 6alpha-methylprednisolone Chemical compound C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)[C@@](O)(C(=O)CO)CC[C@H]21 VHRSUDSXCMQTMA-PJHHCJLFSA-N 0.000 description 1
- OQMZNAMGEHIHNN-UHFFFAOYSA-N 7-Dehydrostigmasterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CC(CC)C(C)C)CCC33)C)C3=CC=C21 OQMZNAMGEHIHNN-UHFFFAOYSA-N 0.000 description 1
- 241000186361 Actinobacteria <class> Species 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- LPZCCMIISIBREI-MTFRKTCUSA-N Citrostadienol Natural products CC=C(CC[C@@H](C)[C@H]1CC[C@H]2C3=CC[C@H]4[C@H](C)[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C LPZCCMIISIBREI-MTFRKTCUSA-N 0.000 description 1
- ACTIUHUUMQJHFO-UHFFFAOYSA-N Coenzym Q10 Natural products COC1=C(OC)C(=O)C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UHFFFAOYSA-N 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- ARVGMISWLZPBCH-UHFFFAOYSA-N Dehydro-beta-sitosterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)CCC(CC)C(C)C)CCC33)C)C3=CC=C21 ARVGMISWLZPBCH-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 210000000712 G cell Anatomy 0.000 description 1
- 208000029422 Hypernatremia Diseases 0.000 description 1
- 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 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 241000186359 Mycobacterium Species 0.000 description 1
- FBWADIKARMIWNM-UHFFFAOYSA-N N-3,5-dichloro-4-hydroxyphenyl-1,4-benzoquinone imine Chemical compound C1=C(Cl)C(O)=C(Cl)C=C1N=C1C=CC(=O)C=C1 FBWADIKARMIWNM-UHFFFAOYSA-N 0.000 description 1
- 101000774651 Naja atra Zinc metalloproteinase-disintegrin-like kaouthiagin-like Proteins 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241001351225 Sergey Species 0.000 description 1
- 240000006394 Sorghum bicolor Species 0.000 description 1
- 229930182558 Sterol Natural products 0.000 description 1
- 241000187747 Streptomyces Species 0.000 description 1
- HZYXFRGVBOPPNZ-UHFFFAOYSA-N UNPD88870 Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)=CCC(CC)C(C)C)C1(C)CC2 HZYXFRGVBOPPNZ-UHFFFAOYSA-N 0.000 description 1
- JXJAJSNUTGVHEG-WLDNQIQOSA-N [2-[(6s,8s,9s,10r,11s,13s,14s,16r,17s)-6-fluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate Chemical compound C1([C@@H](F)C2)=CC(=O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@@H](C)[C@H](C(=O)COC(C)=O)[C@@]2(C)C[C@@H]1O JXJAJSNUTGVHEG-WLDNQIQOSA-N 0.000 description 1
- VLHRIOASVODQEX-WLDNQIQOSA-N [2-[(6s,8s,9s,10r,11s,13s,14s,16r,17s)-6-fluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@@H](C)[C@H](C(=O)COC(C)=O)[C@@]2(C)C[C@@H]1O VLHRIOASVODQEX-WLDNQIQOSA-N 0.000 description 1
- SNMKPDYDNGYYEM-PYAFTSMNSA-N [2-[(8s,10s,13s,14s,16r,17r)-17-hydroxy-10,13,16-trimethyl-3-oxo-2,6,7,8,12,14,15,16-octahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate Chemical compound C([C@H]12)CC3=CC(=O)CC[C@]3(C)C1=CC[C@@]1(C)[C@H]2C[C@@H](C)[C@]1(O)C(=O)COC(C)=O SNMKPDYDNGYYEM-PYAFTSMNSA-N 0.000 description 1
- AAPZMQVULRVUEU-PYAFTSMNSA-N [2-[(8s,10s,13s,14s,16r,17r)-17-hydroxy-10,13,16-trimethyl-3-oxo-7,8,12,14,15,16-hexahydro-6h-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate Chemical compound C([C@H]12)CC3=CC(=O)C=C[C@]3(C)C1=CC[C@@]1(C)[C@H]2C[C@@H](C)[C@]1(O)C(=O)COC(C)=O AAPZMQVULRVUEU-PYAFTSMNSA-N 0.000 description 1
- AAPZMQVULRVUEU-NZDAKWCRSA-N [2-[(8s,10s,13s,14s,16s,17r)-17-hydroxy-10,13,16-trimethyl-3-oxo-7,8,12,14,15,16-hexahydro-6h-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate Chemical compound C([C@H]12)CC3=CC(=O)C=C[C@]3(C)C1=CC[C@@]1(C)[C@H]2C[C@H](C)[C@]1(O)C(=O)COC(C)=O AAPZMQVULRVUEU-NZDAKWCRSA-N 0.000 description 1
- IBKVCXOXJXABNY-SCKJBXJSSA-N [2-[(8s,10s,13s,14s,16s,17r)-17-hydroxy-10,13,16-trimethyl-3-oxo-7,8,12,14,15,16-hexahydro-6h-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] benzoate Chemical compound O=C([C@]1(O)[C@@]2(C)CC=C3[C@@]4(C)C=CC(=O)C=C4CC[C@H]3[C@@H]2C[C@@H]1C)COC(=O)C1=CC=CC=C1 IBKVCXOXJXABNY-SCKJBXJSSA-N 0.000 description 1
- SBUSWJGDMXBNFJ-GACAOOTBSA-N [2-[(8s,10s,13s,14s,17r)-17-hydroxy-10,13-dimethyl-3-oxo-7,8,12,14,15,16-hexahydro-6h-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate Chemical compound O=C1C=C[C@]2(C)C3=CC[C@]4(C)[C@](C(=O)COC(=O)C)(O)CC[C@H]4[C@@H]3CCC2=C1 SBUSWJGDMXBNFJ-GACAOOTBSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000002269 analeptic agent Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- NXQOQNROJJFYCJ-FZFXZXLVSA-N androst-16-ene Chemical compound C1CCC[C@]2(C)[C@H]3CC[C@](C)(C=CC4)[C@@H]4[C@@H]3CCC21 NXQOQNROJJFYCJ-FZFXZXLVSA-N 0.000 description 1
- 229960005471 androstenedione Drugs 0.000 description 1
- AEMFNILZOJDQLW-UHFFFAOYSA-N androstenedione Natural products O=C1CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 AEMFNILZOJDQLW-UHFFFAOYSA-N 0.000 description 1
- 239000012062 aqueous buffer Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- MJVXAPPOFPTTCA-UHFFFAOYSA-N beta-Sistosterol Natural products CCC(CCC(C)C1CCC2C3CC=C4C(C)C(O)CCC4(C)C3CCC12C)C(C)C MJVXAPPOFPTTCA-UHFFFAOYSA-N 0.000 description 1
- NJKOMDUNNDKEAI-UHFFFAOYSA-N beta-sitosterol Natural products CCC(CCC(C)C1CCC2(C)C3CC=C4CC(O)CCC4C3CCC12C)C(C)C NJKOMDUNNDKEAI-UHFFFAOYSA-N 0.000 description 1
- 239000011942 biocatalyst Substances 0.000 description 1
- 230000036983 biotransformation Effects 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 229940107161 cholesterol Drugs 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 239000012084 conversion product Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000000017 cortisol group Chemical group 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000002036 drum drying Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- GAKMQHDJQHZUTJ-ULHLPKEOSA-N fluocortolone Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@@H](C)[C@H](C(=O)CO)[C@@]2(C)C[C@@H]1O GAKMQHDJQHZUTJ-ULHLPKEOSA-N 0.000 description 1
- 229940014144 folate Drugs 0.000 description 1
- 235000019152 folic acid Nutrition 0.000 description 1
- 239000011724 folic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 238000000464 low-speed centrifugation Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000867 polyelectrolyte Polymers 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229960004618 prednisone Drugs 0.000 description 1
- 238000011027 product recovery Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- NPCOQXAVBJJZBQ-UHFFFAOYSA-N reduced coenzyme Q9 Natural products COC1=C(O)C(C)=C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)C(O)=C1OC NPCOQXAVBJJZBQ-UHFFFAOYSA-N 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 150000004666 short chain fatty acids Chemical class 0.000 description 1
- 235000021391 short chain fatty acids Nutrition 0.000 description 1
- KZJWDPNRJALLNS-VJSFXXLFSA-N 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 description 1
- 235000015500 sitosterol Nutrition 0.000 description 1
- 229950005143 sitosterol Drugs 0.000 description 1
- NLQLSVXGSXCXFE-UHFFFAOYSA-N sitosterol Natural products CC=C(/CCC(C)C1CC2C3=CCC4C(C)C(O)CCC4(C)C3CCC2(C)C1)C(C)C NLQLSVXGSXCXFE-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- HCXVJBMSMIARIN-PHZDYDNGSA-N stigmasterol 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)/C=C/[C@@H](CC)C(C)C)[C@@]1(C)CC2 HCXVJBMSMIARIN-PHZDYDNGSA-N 0.000 description 1
- 235000016831 stigmasterol Nutrition 0.000 description 1
- 229940032091 stigmasterol Drugs 0.000 description 1
- BFDNMXAIBMJLBB-UHFFFAOYSA-N stigmasterol Natural products CCC(C=CC(C)C1CCCC2C3CC=C4CC(O)CCC4(C)C3CCC12C)C(C)C BFDNMXAIBMJLBB-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229940035936 ubiquinone Drugs 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- ZYTXTXAMMDTYDQ-DGEXFFLYSA-N vamorolone Chemical compound C([C@H]12)CC3=CC(=O)C=C[C@]3(C)C1=CC[C@@]1(C)[C@H]2C[C@@H](C)[C@]1(O)C(=O)CO ZYTXTXAMMDTYDQ-DGEXFFLYSA-N 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P33/00—Preparation of steroids
- C12P33/02—Dehydrogenating; Dehydroxylating
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Steroid Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US40394982A | 1982-07-30 | 1982-07-30 | |
| US06/436,552 US4524134A (en) | 1982-07-30 | 1982-10-25 | Process for preparing 1,2-dehydro steroids |
| US47543783A | 1983-03-15 | 1983-03-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD213242A5 true DD213242A5 (de) | 1984-09-05 |
Family
ID=27410563
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD25312383A DD213242A5 (de) | 1982-07-30 | 1983-07-15 | Verfahren zur umwandlung von 1,2-gesaettigten steroiden in 1,2-dehydrosteroide |
Country Status (8)
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2568908B1 (fr) * | 1984-08-10 | 1986-12-26 | Doris Dev Richesse Sous Marine | Plate-forme oscillante sur pieux flexibles pour travaux en mer |
| US5380839A (en) * | 1985-09-12 | 1995-01-10 | The Upjohn Company | Phenylpiperazinyl steroids |
| USRE35053E (en) * | 1985-09-12 | 1995-10-10 | The Upjohn Company | Amines useful in producing pharmaceutically active CNS compounds |
| US5099019A (en) * | 1985-09-12 | 1992-03-24 | Upjohn Company | Amines useful in producing pharmaceutically active CNS compounds |
| HU204305B (en) * | 1987-03-12 | 1991-12-30 | Upjohn Co | Process for 1,2-dehydrogenating 3-ketopregnen-21-esters with arthrobacter symplex or bacterium cyclooxydans |
| CN101346460B (zh) * | 2005-12-28 | 2014-05-07 | 味之素株式会社 | 干燥微生物菌体的制造方法 |
| HU227367B1 (en) * | 2007-09-11 | 2011-04-28 | Richter Gedeon Nyrt | Method for producing 6-hydroxymethyl-1,4-androstadiene-3,17-dion |
| NZ603107A (en) | 2008-05-28 | 2014-03-28 | Validus Biopharma Inc | Non-hormonal steroid modulators of nf-kb for treatment of disease |
| US20120178124A1 (en) | 2009-01-07 | 2012-07-12 | Mitsubishi Chemical Corporation | Sterol side chain-cleaving enzyme protein and use thereof |
| WO2011127048A2 (en) | 2010-04-05 | 2011-10-13 | Validus Biopharma | NON-HORMONAL STEROID MODULATORS OF NF-ĸB FOR TREATMENT OF DISEASE |
| WO2017004205A1 (en) | 2015-06-29 | 2017-01-05 | Reveragen Biopharma, Inc. | NON-HORMONAL STEROID MODULATORS OF NF-κB FOR TREATMENT OF DISEASE |
| US11382922B2 (en) | 2019-03-07 | 2022-07-12 | Reveragen Biopharma, Inc. | Aqueous oral pharmaceutical suspension compositions |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB883500A (en) * | 1958-09-15 | 1961-11-29 | Wisconsin Alumni Res Found | Improvements in a microbiological process for the preparation of steroids and ketones |
| FR1262182A (fr) * | 1960-07-01 | 1961-05-26 | Olin Mathieson | Procédé de déshydrogénation sélective du noyau a des stéroïdes |
| US3087864A (en) * | 1961-04-28 | 1963-04-30 | American Cyanamid Co | Process for the 1, 2-hydrogenation of steroids by the use of dried thalli |
| CH414063A (de) * | 1962-11-23 | 1966-05-31 | Eprova Ag | Röntgenkontrastmittel |
| US3360439A (en) * | 1964-08-19 | 1967-12-26 | Squibb & Sons Inc | Process for preparing 1-dehydro steroids |
| US3549498A (en) * | 1968-04-02 | 1970-12-22 | Squibb & Sons Inc | 11alpha-substituted steroids and process |
| FR2285137A1 (fr) * | 1974-09-18 | 1976-04-16 | Roussel Uclaf | Nouveaux derives steroides 17-spirosultines, les g-hydroxyacides correspondants, leur procede de preparation et leur application comme medicament |
| US4035236A (en) * | 1975-10-24 | 1977-07-12 | The Upjohn Company | Process for preparing 9α-hydroxyandrostenedione |
| US4041055A (en) * | 1975-11-17 | 1977-08-09 | The Upjohn Company | Process for the preparation of 17α-hydroxyprogesterones and corticoids from androstenes |
-
1983
- 1983-06-20 DE DE19833322120 patent/DE3322120A1/de active Granted
- 1983-06-27 GB GB08317422A patent/GB2123833B/en not_active Expired
- 1983-07-08 CH CH378483A patent/CH657871A5/de not_active IP Right Cessation
- 1983-07-15 DD DD25312383A patent/DD213242A5/de not_active IP Right Cessation
- 1983-07-20 NL NL8302596A patent/NL8302596A/nl active Search and Examination
- 1983-07-25 JP JP13453683A patent/JPH0614874B2/ja not_active Expired - Lifetime
- 1983-07-27 IE IE176783A patent/IE55533B1/en not_active IP Right Cessation
- 1983-07-29 FR FR8312564A patent/FR2531101B1/fr not_active Expired
-
1984
- 1984-02-01 GB GB08402640A patent/GB2131811B/en not_active Expired
-
1993
- 1993-09-14 JP JP5250926A patent/JPH0824596B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| GB8402640D0 (en) | 1984-03-07 |
| FR2531101B1 (fr) | 1985-11-15 |
| DE3322120C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-10-08 |
| IE831767L (en) | 1984-01-30 |
| GB8317422D0 (en) | 1983-07-27 |
| GB2131811A (en) | 1984-06-27 |
| IE55533B1 (en) | 1990-10-24 |
| GB2131811B (en) | 1986-06-11 |
| GB2123833A (en) | 1984-02-08 |
| DE3322120A1 (de) | 1984-02-02 |
| NL8302596A (nl) | 1984-02-16 |
| JPH0824596B2 (ja) | 1996-03-13 |
| JPH06225792A (ja) | 1994-08-16 |
| CH657871A5 (de) | 1986-09-30 |
| FR2531101A1 (fr) | 1984-02-03 |
| GB2123833B (en) | 1986-06-11 |
| JPS5939299A (ja) | 1984-03-03 |
| JPH0614874B2 (ja) | 1994-03-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP2004838B1 (de) | Verfahren zur herstellung von steroidderivaten durch reduktion von oxosteroidverbindungen oder durch oxidation von hydroxysteroidverbindungen unter verwendung einer hydroxysteroiddehydrogenase | |
| DE3322120C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| US4524134A (en) | Process for preparing 1,2-dehydro steroids | |
| US4749649A (en) | Microbial Δ1-dehydrogenation process using a scavenger of toxic oxygen | |
| DE3235884C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| EP0014991B1 (de) | Mikrobiologisches Verfahren zur Herstellung 7-alpha-hydroxylierter Steroide | |
| US2863806A (en) | 17alpha hydroxylation of steroids by trichoderma viride | |
| US4704358A (en) | Δ1 -dehydrogenation with heat or air-dried B. cyclooxidans | |
| DE60306768T2 (de) | Prozess für die dehydrogenierung von azaandrostanverbindungen | |
| EP2093285B1 (en) | Method for biocatalysis using filamentous fungi | |
| DE1593327C (de) | Verfahren zur Herstellung von Delta hoch 1,4 -Androstadien-3,17-dion, Delta hoch 1,4 -Androstadien-3,11,17-trion bzw. Delta hoch 1,4 -Androstadien-1 lalpha-ol-3,17-dion | |
| DE956952C (de) | Verfahren zur Herstellung von oxydierten Steroiden | |
| DE1909152A1 (de) | Verfahren zur Herstellung von 11 alpha-Hydroxy-3-oxo-delta?-Steroiden der Pregnan- und Androstanreihe mittels Mischfermentation | |
| DE936207C (de) | Verfahren zur Herstellung von oxydierten Steroiden | |
| DE1181703B (de) | Verfahren zur mikrobiologischen Umwandlung von Steroiden und Fettsaeuren | |
| DE1205092B (de) | Verfahren zur Herstellung von im Ring A gesaettigten 3-Keto-steroiden auf mikrobiologischem Wege | |
| DE1128854B (de) | Verfahren zur Herstellung von 11-hydroxylierten Steroiden der Pregnanreihe | |
| DE1021845B (de) | Verfahren zur Dehydrierung und bzw. oder zum oxydativen Abbau der 17-staendigen Seitenkette von Steroiden | |
| DE1768978A1 (de) | Verfahren zur Entfernung von Seitenketten von Sapogeninen | |
| HU196847B (hu) | Uj eljárás 1,2-dehidro-szteroidok előállítására | |
| DE1231697B (de) | Verfahren zur Herstellung von 11alpha-Oxy-delta 4-3-ketosteroiden | |
| DEC0009818MA (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| DD152581A1 (de) | Verfahren zur herstellung von 20-carboxypregna-1,4-dien-3-on | |
| DE1005961B (de) | Verfahren zur Herstellung von Polyoxysteroiden der Pregnanreihe | |
| IE55534B1 (en) | Steroid bioconversion |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ENJ | Ceased due to non-payment of renewal fee |