TW200406419A - 5-Androsten-3 β- ol steroid intermediates and processes for their preparation - Google Patents
5-Androsten-3 β- ol steroid intermediates and processes for their preparation Download PDFInfo
- Publication number
- TW200406419A TW200406419A TW092106331A TW92106331A TW200406419A TW 200406419 A TW200406419 A TW 200406419A TW 092106331 A TW092106331 A TW 092106331A TW 92106331 A TW92106331 A TW 92106331A TW 200406419 A TW200406419 A TW 200406419A
- Authority
- TW
- Taiwan
- Prior art keywords
- scope
- steroid
- formula
- item
- preparing
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 124
- 238000002360 preparation method Methods 0.000 title claims abstract description 49
- -1 5-Androsten-3 β- ol steroid Chemical class 0.000 title claims abstract description 26
- 239000000543 intermediate Substances 0.000 title abstract description 12
- LYFPAZBMEUSVNA-UHFFFAOYSA-N (10R)-3c-Hydroxy-10r.13c-dimethyl-(8cH.9tH.14tH)-Delta5-tetradecahydro-1H-cyclopenta[a]phenanthren Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCCC1(C)CC2 LYFPAZBMEUSVNA-UHFFFAOYSA-N 0.000 title abstract 2
- 150000003431 steroids Chemical class 0.000 claims description 164
- 150000002596 lactones Chemical group 0.000 claims description 51
- 229910052799 carbon Inorganic materials 0.000 claims description 44
- 238000000855 fermentation Methods 0.000 claims description 36
- 230000004151 fermentation Effects 0.000 claims description 36
- 125000004432 carbon atom Chemical group C* 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 241000233866 Fungi Species 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 21
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 19
- 150000002576 ketones Chemical class 0.000 claims description 16
- 239000007787 solid Substances 0.000 claims description 16
- 239000012141 concentrate Substances 0.000 claims description 15
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- 102000004190 Enzymes Human genes 0.000 claims description 9
- 108090000790 Enzymes Proteins 0.000 claims description 9
- 229930182558 Sterol Natural products 0.000 claims description 9
- 238000005805 hydroxylation reaction Methods 0.000 claims description 9
- 150000003432 sterols Chemical class 0.000 claims description 9
- 235000003702 sterols Nutrition 0.000 claims description 9
- 150000005847 Δ5 steroids Chemical class 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 230000004044 response Effects 0.000 claims description 7
- 241000894006 Bacteria Species 0.000 claims description 6
- 241000589516 Pseudomonas Species 0.000 claims description 6
- TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical compound C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 claims description 5
- 229920000742 Cotton Polymers 0.000 claims description 5
- 241000222350 Pleurotus Species 0.000 claims description 5
- 241000894007 species Species 0.000 claims description 5
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- VWFCWHWCCOZKJZ-CAMMJAKZSA-N (8s,10s,13s,14s)-10,13-dimethyl-2,3,4,7,8,12,14,15,16,17-decahydro-1h-cyclopenta[a]phenanthrene Chemical compound C([C@H]12)C=C3CCCC[C@]3(C)C1=CC[C@@]1(C)[C@H]2CCC1 VWFCWHWCCOZKJZ-CAMMJAKZSA-N 0.000 claims description 3
- 241000186427 Cutibacterium acnes Species 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 230000008030 elimination Effects 0.000 claims description 3
- 238000003379 elimination reaction Methods 0.000 claims description 3
- HFVMLYAGWXSTQI-QYXZOKGRSA-N 5alpha-androst-16-en-3-one Chemical compound C1C(=O)CC[C@]2(C)[C@H]3CC[C@](C)(C=CC4)[C@@H]4[C@@H]3CC[C@H]21 HFVMLYAGWXSTQI-QYXZOKGRSA-N 0.000 claims description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 2
- 240000004922 Vigna radiata Species 0.000 claims description 2
- 206010052428 Wound Diseases 0.000 claims description 2
- 208000027418 Wounds and injury Diseases 0.000 claims description 2
- 230000003637 steroidlike Effects 0.000 claims description 2
- 239000013589 supplement Substances 0.000 claims description 2
- KVUXYQHEESDGIJ-UHFFFAOYSA-N 10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthrene-3,16-diol Chemical compound C1CC2CC(O)CCC2(C)C2C1C1CC(O)CC1(C)CC2 KVUXYQHEESDGIJ-UHFFFAOYSA-N 0.000 claims 51
- 241000233614 Phytophthora Species 0.000 claims 4
- 239000003098 androgen Substances 0.000 claims 3
- 229940030486 androgens Drugs 0.000 claims 2
- 230000036755 cellular response Effects 0.000 claims 2
- KVGZZAHHUNAVKZ-UHFFFAOYSA-N 1,4-Dioxin Chemical group O1C=COC=C1 KVGZZAHHUNAVKZ-UHFFFAOYSA-N 0.000 claims 1
- 241000228257 Aspergillus sp. Species 0.000 claims 1
- 241000732800 Cymbidium Species 0.000 claims 1
- 241000255967 Helicoverpa zea Species 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- 238000010586 diagram Methods 0.000 claims 1
- 150000002220 fluorenes Chemical class 0.000 claims 1
- 239000010977 jade Substances 0.000 claims 1
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 claims 1
- 229910052702 rhenium Inorganic materials 0.000 claims 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical group [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 47
- 239000002609 medium Substances 0.000 description 37
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 29
- 230000036983 biotransformation Effects 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 239000000047 product Substances 0.000 description 27
- 239000000203 mixture Substances 0.000 description 25
- 239000002002 slurry Substances 0.000 description 21
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 21
- 238000011081 inoculation Methods 0.000 description 20
- 238000011218 seed culture Methods 0.000 description 20
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 19
- 239000013078 crystal Substances 0.000 description 19
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 18
- 239000001301 oxygen Substances 0.000 description 18
- 229910052760 oxygen Inorganic materials 0.000 description 18
- 235000019439 ethyl acetate Nutrition 0.000 description 17
- 235000015097 nutrients Nutrition 0.000 description 17
- 238000004659 sterilization and disinfection Methods 0.000 description 17
- 239000000284 extract Substances 0.000 description 16
- 239000012071 phase Substances 0.000 description 16
- 235000013405 beer Nutrition 0.000 description 13
- 238000002425 crystallisation Methods 0.000 description 12
- 230000008025 crystallization Effects 0.000 description 12
- 239000011159 matrix material Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 238000001914 filtration Methods 0.000 description 11
- 239000010410 layer Substances 0.000 description 11
- 239000003921 oil Substances 0.000 description 10
- 235000019198 oils Nutrition 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000013019 agitation Methods 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 238000005119 centrifugation Methods 0.000 description 7
- 230000002538 fungal effect Effects 0.000 description 7
- 150000002431 hydrogen Chemical class 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- 230000001954 sterilising effect Effects 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000003549 soybean oil Substances 0.000 description 6
- 235000012424 soybean oil Nutrition 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- SBNLPRGISFUZQE-VMXHOPILSA-N (8s,9s,10r,13s,14s)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthrene Chemical compound C1C=C2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 SBNLPRGISFUZQE-VMXHOPILSA-N 0.000 description 5
- 235000010469 Glycine max Nutrition 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 235000013312 flour Nutrition 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical class C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 4
- 241001147381 Helicoverpa armigera Species 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- 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 4
- 239000012267 brine Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000009413 insulation Methods 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- 238000001223 reverse osmosis Methods 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 239000004575 stone Substances 0.000 description 4
- 229920001285 xanthan gum Polymers 0.000 description 4
- NYGWTZLABYSHOP-FCYODTKKSA-N (8R,9S,10S,13R)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12-decahydro-1H-cyclopenta[a]phenanthrene Chemical class C([C@H]12)CC3CCCC[C@]3(C)[C@H]1CC[C@@]1(C)C2=CC=C1 NYGWTZLABYSHOP-FCYODTKKSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- 239000004375 Dextrin Substances 0.000 description 3
- 229920001353 Dextrin Polymers 0.000 description 3
- 241000186359 Mycobacterium Species 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- NBAOBYTXAFOGGD-BCYZHJNNSA-N [(8r,9s,10r,13r,14s)-10-methyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-13-yl]methanol Chemical compound C1C[C@@H]2[C@](CCCC3)(C)C3=CC[C@H]2[C@@H]2CCC[C@]21CO NBAOBYTXAFOGGD-BCYZHJNNSA-N 0.000 description 3
- 239000004568 cement Substances 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 235000019425 dextrin Nutrition 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- JUKPWJGBANNWMW-VWBFHTRKSA-N eplerenone Chemical compound C([C@@H]1[C@]2(C)C[C@H]3O[C@]33[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)C(=O)OC)C[C@@]21CCC(=O)O1 JUKPWJGBANNWMW-VWBFHTRKSA-N 0.000 description 3
- 229960001208 eplerenone Drugs 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000001963 growth medium Substances 0.000 description 3
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 3
- 238000007654 immersion Methods 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 3
- MDHIWBNJNHUBJL-VMXHOPILSA-N (8s,9s,10r,13r,14s)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1h-cyclopenta[a]phenanthrene Chemical compound C1CCC[C@]2(C)[C@H]3CC[C@](C)(C=CC4)[C@@H]4[C@@H]3CC=C21 MDHIWBNJNHUBJL-VMXHOPILSA-N 0.000 description 2
- 241000235389 Absidia Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 240000008564 Boehmeria nivea Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 241000256257 Heliothis Species 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 229910019093 NaOCl Inorganic materials 0.000 description 2
- 235000019483 Peanut oil Nutrition 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 244000299461 Theobroma cacao Species 0.000 description 2
- 235000009470 Theobroma cacao Nutrition 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- GFHNAMRJFCEERV-UHFFFAOYSA-L cobalt chloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Co+2] GFHNAMRJFCEERV-UHFFFAOYSA-L 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 235000005687 corn oil Nutrition 0.000 description 2
- 239000002285 corn oil Substances 0.000 description 2
- 235000012343 cottonseed oil Nutrition 0.000 description 2
- 239000002385 cottonseed oil Substances 0.000 description 2
- 239000013530 defoamer Substances 0.000 description 2
- 238000005906 dihydroxylation reaction Methods 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 239000008169 grapeseed oil Substances 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 150000007857 hydrazones Chemical class 0.000 description 2
- 230000033444 hydroxylation Effects 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000000944 linseed oil Substances 0.000 description 2
- 235000021388 linseed oil Nutrition 0.000 description 2
- WRUGWIBCXHJTDG-UHFFFAOYSA-L magnesium sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Mg+2].[O-]S([O-])(=O)=O WRUGWIBCXHJTDG-UHFFFAOYSA-L 0.000 description 2
- 229940061634 magnesium sulfate heptahydrate Drugs 0.000 description 2
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 2
- 230000000813 microbial effect Effects 0.000 description 2
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 2
- 235000019796 monopotassium phosphate Nutrition 0.000 description 2
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 2
- 239000004006 olive oil Substances 0.000 description 2
- 235000008390 olive oil Nutrition 0.000 description 2
- 239000000312 peanut oil Substances 0.000 description 2
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000001965 potato dextrose agar Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 238000010025 steaming Methods 0.000 description 2
- FBWNMEQMRUMQSO-UHFFFAOYSA-N tergitol NP-9 Chemical compound CCCCCCCCCC1=CC=C(OCCOCCOCCOCCOCCOCCOCCOCCOCCO)C=C1 FBWNMEQMRUMQSO-UHFFFAOYSA-N 0.000 description 2
- 239000010497 wheat germ oil Substances 0.000 description 2
- MGAXYKDBRBNWKT-UHFFFAOYSA-N (5-oxooxolan-2-yl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1OC(=O)CC1 MGAXYKDBRBNWKT-UHFFFAOYSA-N 0.000 description 1
- AFGDPPHTYUQKOF-QAGGRKNESA-N (8r,9s,10r,13s,14s)-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one Chemical class C1CCC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC=C21 AFGDPPHTYUQKOF-QAGGRKNESA-N 0.000 description 1
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 1
- KRVXMNNRSSQZJP-PHFHYRSDSA-N 5alpha-androst-16-en-3alpha-ol Chemical compound C1[C@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C=CC4)[C@@H]4[C@@H]3CC[C@H]21 KRVXMNNRSSQZJP-PHFHYRSDSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 241000193830 Bacillus <bacterium> Species 0.000 description 1
- 241000194110 Bacillus sp. (in: Bacteria) Species 0.000 description 1
- MECSTUBFDQNJLT-UHFFFAOYSA-N C1(=CC=CC=2C3=CC=CC=C3CC12)C1(NC(CCC1)(C1=CC=CC=2C3=CC=CC=C3CC12)C1=CC=CC=2C3=CC=CC=C3CC12)C1=CC=CC=2C3=CC=CC=C3CC12 Chemical compound C1(=CC=CC=2C3=CC=CC=C3CC12)C1(NC(CCC1)(C1=CC=CC=2C3=CC=CC=C3CC12)C1=CC=CC=2C3=CC=CC=C3CC12)C1=CC=CC=2C3=CC=CC=C3CC12 MECSTUBFDQNJLT-UHFFFAOYSA-N 0.000 description 1
- 241000282465 Canis Species 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- GXGJIOMUZAGVEH-UHFFFAOYSA-N Chamazulene Chemical group CCC1=CC=C(C)C2=CC=C(C)C2=C1 GXGJIOMUZAGVEH-UHFFFAOYSA-N 0.000 description 1
- 241000588881 Chromobacterium Species 0.000 description 1
- 241000941525 Chromobacterium sp. Species 0.000 description 1
- 235000007516 Chrysanthemum Nutrition 0.000 description 1
- 244000189548 Chrysanthemum x morifolium Species 0.000 description 1
- 241000224483 Coccidia Species 0.000 description 1
- 241000223218 Fusarium Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- 241000186660 Lactobacillus Species 0.000 description 1
- 241000190144 Lasiodiplodia theobromae Species 0.000 description 1
- 102000008109 Mixed Function Oxygenases Human genes 0.000 description 1
- 108010074633 Mixed Function Oxygenases Proteins 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- 229910052778 Plutonium Inorganic materials 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 208000003251 Pruritus Diseases 0.000 description 1
- 241001361634 Rhizoctonia Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- 241000002828 Thelonectria lucida Species 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- KRVXMNNRSSQZJP-UHFFFAOYSA-N beta-androstenol Natural products C1C(O)CCC2(C)C3CCC(C)(C=CC4)C4C3CCC21 KRVXMNNRSSQZJP-UHFFFAOYSA-N 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- AHZOHFYNIDGBKN-UHFFFAOYSA-N chloro(ethoxy)phosphinic acid Chemical compound CCOP(O)(Cl)=O AHZOHFYNIDGBKN-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 210000000078 claw Anatomy 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000011549 crystallization solution Substances 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- AXDDJHKBOYNJPY-UHFFFAOYSA-L dipotassium;carboxylato carbonate Chemical compound [K+].[K+].[O-]C(=O)OC([O-])=O AXDDJHKBOYNJPY-UHFFFAOYSA-L 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- QBIRIYASLUPKQB-CBHLJOAQSA-N epierenone Chemical compound C1([C@]2(C)[C@H]3O[C@H]3C3[C@@]4(C)CCC(=O)C=C4C[C@H](C13)C(=O)OC)CC[C@@]21CCC(=O)O1 QBIRIYASLUPKQB-CBHLJOAQSA-N 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 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 1
- 239000012634 fragment Substances 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 235000020256 human milk Nutrition 0.000 description 1
- 210000004251 human milk Anatomy 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000036737 immune function Effects 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 229940039696 lactobacillus Drugs 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- UYDLBVPAAFVANX-UHFFFAOYSA-N octylphenoxy polyethoxyethanol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(OCCOCCOCCOCCO)C=C1 UYDLBVPAAFVANX-UHFFFAOYSA-N 0.000 description 1
- 235000021542 oral nutrition Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- 150000004686 pentahydrates Chemical class 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- OYEHPCDNVJXUIW-UHFFFAOYSA-N plutonium atom Chemical group [Pu] OYEHPCDNVJXUIW-UHFFFAOYSA-N 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 235000015170 shellfish Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 125000002345 steroid group Chemical group 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 235000020238 sunflower seed Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000010257 thawing Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000012991 xanthate Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0003—Androstane derivatives
- C07J1/0011—Androstane derivatives substituted in position 17 by a keto group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J21/001—Lactones
- C07J21/003—Lactones at position 17
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US40399002P | 2002-08-16 | 2002-08-16 | |
| US41529302P | 2002-10-01 | 2002-10-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW200406419A true TW200406419A (en) | 2004-05-01 |
Family
ID=31891414
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW092106331A TW200406419A (en) | 2002-08-16 | 2003-03-21 | 5-Androsten-3 β- ol steroid intermediates and processes for their preparation |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US20040034215A1 (enExample) |
| EP (1) | EP1534732B1 (enExample) |
| JP (1) | JP2006507369A (enExample) |
| AT (1) | ATE339437T1 (enExample) |
| AU (1) | AU2003285485A1 (enExample) |
| BR (1) | BR0313523A (enExample) |
| CA (1) | CA2495412A1 (enExample) |
| DE (1) | DE60308388T2 (enExample) |
| ES (1) | ES2271636T3 (enExample) |
| MX (1) | MXPA05001857A (enExample) |
| TW (1) | TW200406419A (enExample) |
| WO (1) | WO2004016640A2 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110885869A (zh) * | 2019-12-24 | 2020-03-17 | 天津科技大学 | 一种利用微生物转化生产7α-羟基-脱氢表雄酮的方法 |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ITMI20042338A1 (it) * | 2004-12-06 | 2005-03-06 | Ind Chimica Srl | Processo per la preparazione di drospirenone |
| US8084446B2 (en) * | 2005-04-26 | 2011-12-27 | Eric Marchewitz | Use of DHEA derivatives for enhancing physical performance |
| PL2527356T3 (pl) * | 2005-07-21 | 2018-06-29 | Bayer Intellectual Property Gmbh | Sposób wytwarzania 3-okso-pregn-4-eno-21,17-karbolaktonów za pomocą wolnego od metali utleniania 17-(3-hydroksypropylo)-3,17- dihydroksyandrostanów |
| ATE403668T1 (de) | 2005-07-21 | 2008-08-15 | Bayer Schering Pharma Ag | Verfahren zur herstellung von 3-oxo-pregn-4-en-21,17-carbolactonen durch die metallfreie oxidation von 17-(3-hydroxypropyl)-3,17- dihydroxyandrostanen |
| US7319154B2 (en) | 2005-07-21 | 2008-01-15 | Bayer Schering Pharma Ag | Process for the production of 3-oxo-pregn-4-ene-21, 17-carbolactones by the metal free oxidation of 17-(3-hydroxypropyl)-3, 17-dihydroxyandrostanes |
| CN110331182A (zh) * | 2019-08-06 | 2019-10-15 | 江苏远大仙乐药业有限公司 | 一种甾体中间体的生物转化制备方法 |
| CN111057734A (zh) * | 2019-12-24 | 2020-04-24 | 天津科技大学 | 一种甲基睾丸素高效转化生产11α-羟基-甲基睾丸素的方法 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3294646A (en) * | 1963-10-23 | 1966-12-27 | American Home Prod | Microbiological hydroxylation of norsteroids using aspergillus ochraceus |
| DE2349022A1 (de) * | 1973-09-26 | 1975-04-10 | Schering Ag | Neue d-homo-steroide |
| DK134348C (da) * | 1973-11-30 | 1977-03-21 | Schering Ag | Analogifremgangsmade til fremstilling af d-homo-20-ketopregnaner |
| US4031074A (en) * | 1974-09-02 | 1977-06-21 | Akzona Incorporated | Process for the preparation of 11β-hydroxy-18-alkyl-estrane compounds |
| IL48628A0 (en) * | 1974-12-23 | 1976-02-29 | Schering Ag | D-homo-20-keto-pregnanes and process for their manufactur |
| US4054563A (en) * | 1975-04-25 | 1977-10-18 | Ciba-Geigy Corporation | Process for the manufacture of spiro compounds of the steroid series |
| CH633562A5 (de) * | 1976-12-10 | 1982-12-15 | Schering Ag | Verfahren zur herstellung neuer kortikoide. |
| US4336332A (en) * | 1979-02-20 | 1982-06-22 | Hoffmann-La Roche, Inc. | Process for the manufacture of hydroxylated steroids |
| DE3042136A1 (de) * | 1980-11-03 | 1982-06-09 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Verfahren zur herstellung von 3 (beta), 7 (beta) -dihydroxy- (delta) (pfeil hoch)5(pfeil hoch) -steroiden |
| US4559332A (en) * | 1983-04-13 | 1985-12-17 | Ciba Geigy Corporation | 20-Spiroxanes and analogues having an open ring E, processes for their manufacture, and pharmaceutical preparations thereof |
| AU7978794A (en) * | 1993-10-13 | 1995-05-04 | Neurocrine Biosciences, Inc. | 3,17-dihydroxy-3,7,16 and/or 17-methyl-androst-5-ene compounds, derivatives thereof, and their use |
| PT973791E (pt) * | 1995-12-11 | 2007-09-26 | Searle Llc | Processo para a preparação de um composto epoxi |
| DE69620474T2 (de) * | 1995-12-12 | 2002-11-14 | Akzo Nobel N.V., Arnhem | Mikrobielle 11alpha-hydroxylierung von steroiden |
| FR2771105A1 (fr) | 1997-11-20 | 1999-05-21 | Vitasterol | Utilisation du fusarium monoliforme pour la preparation des derives 7alpha-hydroxyles de la dehydroepiandrosterone et de la pregnenolone |
-
2003
- 2003-03-21 DE DE60308388T patent/DE60308388T2/de not_active Expired - Fee Related
- 2003-03-21 CA CA002495412A patent/CA2495412A1/en not_active Abandoned
- 2003-03-21 TW TW092106331A patent/TW200406419A/zh unknown
- 2003-03-21 MX MXPA05001857A patent/MXPA05001857A/es unknown
- 2003-03-21 WO PCT/US2003/007791 patent/WO2004016640A2/en not_active Ceased
- 2003-03-21 AU AU2003285485A patent/AU2003285485A1/en not_active Abandoned
- 2003-03-21 US US10/392,955 patent/US20040034215A1/en not_active Abandoned
- 2003-03-21 AT AT03756776T patent/ATE339437T1/de not_active IP Right Cessation
- 2003-03-21 ES ES03756776T patent/ES2271636T3/es not_active Expired - Lifetime
- 2003-03-21 JP JP2005502036A patent/JP2006507369A/ja not_active Abandoned
- 2003-03-21 EP EP03756776A patent/EP1534732B1/en not_active Expired - Lifetime
- 2003-03-21 BR BR0313523-3A patent/BR0313523A/pt not_active IP Right Cessation
-
2004
- 2004-06-01 US US10/858,177 patent/US7002028B2/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110885869A (zh) * | 2019-12-24 | 2020-03-17 | 天津科技大学 | 一种利用微生物转化生产7α-羟基-脱氢表雄酮的方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2006507369A (ja) | 2006-03-02 |
| MXPA05001857A (es) | 2005-06-03 |
| WO2004016640A3 (en) | 2004-07-08 |
| BR0313523A (pt) | 2005-06-28 |
| CA2495412A1 (en) | 2004-02-26 |
| DE60308388T2 (de) | 2007-09-20 |
| US20040034215A1 (en) | 2004-02-19 |
| EP1534732A2 (en) | 2005-06-01 |
| US7002028B2 (en) | 2006-02-21 |
| ES2271636T3 (es) | 2007-04-16 |
| WO2004016640A2 (en) | 2004-02-26 |
| AU2003285485A1 (en) | 2004-03-03 |
| US20040220158A1 (en) | 2004-11-04 |
| ATE339437T1 (de) | 2006-10-15 |
| DE60308388D1 (de) | 2006-10-26 |
| EP1534732B1 (en) | 2006-09-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP1562974B1 (en) | Processes for preparing c-7 substituted 5-androstenes | |
| JP2004524858A (ja) | ステロールをアンドロステ−4−エン−3,17−ジオン/アンドロスタ−1,4−ジエン−3,17−ジオンに転換する能力を有する微生物及びその調製方法及び使用 | |
| CN102206696A (zh) | 11,17α-被取代的孕甾-1,4-二烯-3,20-二酮的制备方法 | |
| TW200406419A (en) | 5-Androsten-3 β- ol steroid intermediates and processes for their preparation | |
| CN102061320A (zh) | 11α,17α-二羟基-雄甾-4-烯-3,20-二酮的制备方法 | |
| EP2173761B1 (en) | Process for the synthesis of 9-alpha-hydroxy-steroids | |
| TW200525036A (en) | Microbial method for hydrolysis and oxidation of androst-5-ene and pregn-5-ene steroid esters | |
| JPS6137280B2 (enExample) | ||
| HU227367B1 (en) | Method for producing 6-hydroxymethyl-1,4-androstadiene-3,17-dion | |
| US20070066579A1 (en) | 5-androsten-3beta-ol steroid intermediates and processs for their preparation | |
| US20060100185A1 (en) | 5-Androsten-3beta-ol steroid intermediates and processes for their preparation | |
| JP2004535805A (ja) | 11β,17α,21−トリヒドロキシ−6α−メチルプレグナ−1,4−ジエン−3,20−ジオン21−アセテートの製法 | |
| CN104046675B (zh) | 利用含有羟化酶的发酵液生产11α-羟基坎利酮的方法 | |
| JPS6250118B2 (enExample) | ||
| JPS6251116B2 (enExample) | ||
| CN116034165A (zh) | 制备熊胆酸的微生物方法 | |
| EP1679317A2 (en) | 5-Androsten-3 -ol steroid intermediates and processes for fheir preparation | |
| JPS6357437B2 (enExample) | ||
| JPS59187000A (ja) | アンドロスタ−1,4,11(12)−トリエン−3,17−ジオン |