DD139859A5 - Verfahren zur herstellung von 21-hydroxy-20-methylpregnanen - Google Patents

Verfahren zur herstellung von 21-hydroxy-20-methylpregnanen Download PDF

Info

Publication number: DD139859A5
Authority: DD; German Democratic Republic
Prior art keywords: borate; fermentation; item; culture; hydroxy
Prior art date: 1977-12-19

Application number

DD78209813A

Other languages

German (de)

English (en)

Inventor

Alfred Weber

Mario Kennecke

Rudolf Mueller

Original Assignee

Schering Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1977-12-19

Filing date

1978-12-15

Publication date

1980-01-23

1978-12-15 Application filed by Schering Ag filed Critical Schering Ag

1980-01-23 Publication of DD139859A5 publication Critical patent/DD139859A5/de

Links

238000004519 manufacturing process Methods 0.000 title 1
238000000855 fermentation Methods 0.000 claims description 16
230000004151 fermentation Effects 0.000 claims description 16
241000187488 Mycobacterium sp. Species 0.000 claims description 13
238000000034 method Methods 0.000 claims description 13
-1 borate ions Chemical class 0.000 claims description 6
239000003795 chemical substances by application Substances 0.000 claims description 6
150000001639 boron compounds Chemical class 0.000 claims description 5
229940068065 phytosterols Drugs 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
MDCWDBMBZLORER-UHFFFAOYSA-N triphenyl borate Chemical compound C=1C=CC=CC=1OB(OC=1C=CC=CC=1)OC1=CC=CC=C1 MDCWDBMBZLORER-UHFFFAOYSA-N 0.000 claims description 3
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 2
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
229910052784 alkaline earth metal Inorganic materials 0.000 claims 2
239000002253 acid Substances 0.000 claims 1
239000003513 alkali Substances 0.000 claims 1
229960002645 boric acid Drugs 0.000 claims 1
235000010338 boric acid Nutrition 0.000 claims 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
125000004043 oxo group Chemical group O=* 0.000 claims 1
VGTPKLINSHNZRD-UHFFFAOYSA-N oxoborinic acid Chemical compound OB=O VGTPKLINSHNZRD-UHFFFAOYSA-N 0.000 claims 1
239000000758 substrate Substances 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
239000000243 solution Substances 0.000 description 6
239000000839 emulsion Substances 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
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 4
238000006243 chemical reaction Methods 0.000 description 4
235000015500 sitosterol Nutrition 0.000 description 4
150000003431 steroids Chemical class 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
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 3
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 3
AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 3
WTGKYGZEGOFNLC-VHVURGOWSA-N 2-[(8R,9S,10S,13S,14S,17S)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]prop-1-en-1-ol Chemical compound OC=C([C@H]1CC[C@H]2[C@@H]3CCC4CCCC[C@]4(C)[C@H]3CC[C@]12C)C WTGKYGZEGOFNLC-VHVURGOWSA-N 0.000 description 3
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 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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 3
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 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
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 3
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 3
229910021538 borax Inorganic materials 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
239000002609 medium Substances 0.000 description 3
235000015097 nutrients Nutrition 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
238000011218 seed culture Methods 0.000 description 3
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 3
229950005143 sitosterol Drugs 0.000 description 3
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 3
235000010339 sodium tetraborate Nutrition 0.000 description 3
239000002904 solvent Substances 0.000 description 3
BQTTYKVRRLHMQQ-ZBKBXNIDSA-N (8r,9s,10s,13r,14s,17r)-17-ethenyl-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one Chemical compound C1C(=O)CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)C=C)[C@@H]4[C@@H]3CCC21 BQTTYKVRRLHMQQ-ZBKBXNIDSA-N 0.000 description 2
ZNWOYQVXPIEQRC-ZRFCQXGJSA-N (8s,9s,10r,13s,14s,17r)-17-(1-hydroxypropan-2-yl)-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(CO)C)[C@@]1(C)CC2 ZNWOYQVXPIEQRC-ZRFCQXGJSA-N 0.000 description 2
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
UVSXVPOQDZNKET-QSZBOJPKSA-N 2-[(8r,9s,10s,13s,14s,17r)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]propan-1-ol Chemical class C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(CO)C)[C@@]1(C)CC2 UVSXVPOQDZNKET-QSZBOJPKSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
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 2
229930182558 Sterol Natural products 0.000 description 2
230000001580 bacterial effect Effects 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000006161 blood agar Substances 0.000 description 2
239000012267 brine Substances 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
KZJWDPNRJALLNS-FBZNIEFRSA-N clionasterol 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-FBZNIEFRSA-N 0.000 description 2
UQGFMSUEHSUPRD-UHFFFAOYSA-N disodium;3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound [Na+].[Na+].O1B([O-])OB2OB([O-])OB1O2 UQGFMSUEHSUPRD-UHFFFAOYSA-N 0.000 description 2
238000004945 emulsification Methods 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
230000001804 emulsifying effect Effects 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
229910000402 monopotassium phosphate Inorganic materials 0.000 description 2
235000019796 monopotassium phosphate Nutrition 0.000 description 2
PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000004328 sodium tetraborate Substances 0.000 description 2
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
150000003432 sterols Chemical class 0.000 description 2
235000003702 sterols Nutrition 0.000 description 2
239000000725 suspension Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
238000012360 testing method Methods 0.000 description 2
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
LGJMUZUPVCAVPU-ANOYILKDSA-N (3s,8r,9s,10s,13r,14s,17r)-17-[(2r,5s)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-ol Chemical class C1CC2C[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 LGJMUZUPVCAVPU-ANOYILKDSA-N 0.000 description 1
UDTOICJKWLQCDX-USUWBSJTSA-N (8S,9S,10R,13R,14S,17S)-10,13-dimethyl-17-propyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CCC)[C@@]1(C)CC2 UDTOICJKWLQCDX-USUWBSJTSA-N 0.000 description 1
VWYOARFPMUBYFG-ZTPZMMAUSA-N (8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylhept-6-en-2-yl]-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one Chemical compound C1CC2CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@@H](CCCC(C)=C)C)[C@@]1(C)CC2 VWYOARFPMUBYFG-ZTPZMMAUSA-N 0.000 description 1
NWNSDNWCYSYUMD-VHVURGOWSA-N (8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-propan-2-yl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthrene Chemical class C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(C)C)[C@@]1(C)CC2 NWNSDNWCYSYUMD-VHVURGOWSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
NRESKKGDHRQEMH-HPGXARPTSA-N 2-[(8r,9s,10s,13s,14s,17r)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]propanoic acid Chemical class C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(C)C(O)=O)[C@@]1(C)CC2 NRESKKGDHRQEMH-HPGXARPTSA-N 0.000 description 1
WTLKTXIHIHFSGU-UHFFFAOYSA-N 2-nitrosoguanidine Chemical compound NC(N)=NN=O WTLKTXIHIHFSGU-UHFFFAOYSA-N 0.000 description 1
GDTSJMKGXGJFGQ-UHFFFAOYSA-N 3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound O1B([O-])OB2OB([O-])OB1O2 GDTSJMKGXGJFGQ-UHFFFAOYSA-N 0.000 description 1
XMRPGKVKISIQBV-BJMCWZGWSA-N 5alpha-pregnane-3,20-dione Chemical class C([C@@H]1CC2)C(=O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)C)[C@@]2(C)CC1 XMRPGKVKISIQBV-BJMCWZGWSA-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
241000894006 Bacteria Species 0.000 description 1
SGNBVLSWZMBQTH-FGAXOLDCSA-N Campesterol 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)C)C)CC4)CC3)CC=2)CC1 SGNBVLSWZMBQTH-FGAXOLDCSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
BTEISVKTSQLKST-UHFFFAOYSA-N Haliclonasterol Natural products CC(C=CC(C)C(C)(C)C)C1CCC2C3=CC=C4CC(O)CCC4(C)C3CCC12C BTEISVKTSQLKST-UHFFFAOYSA-N 0.000 description 1
238000006036 Oppenauer oxidation reaction Methods 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
150000001242 acetic acid derivatives Chemical class 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
239000004327 boric acid Substances 0.000 description 1
238000009395 breeding Methods 0.000 description 1
230000001488 breeding effect Effects 0.000 description 1
ILOKQJWLMPPMQU-UHFFFAOYSA-N calcium;oxido(oxo)borane Chemical compound [Ca+2].[O-]B=O.[O-]B=O ILOKQJWLMPPMQU-UHFFFAOYSA-N 0.000 description 1
QQIOPZFVTIHASB-IMUDCKKOSA-N campest-4-en-3-one Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](C)C(C)C)[C@@]1(C)CC2 QQIOPZFVTIHASB-IMUDCKKOSA-N 0.000 description 1
SGNBVLSWZMBQTH-PODYLUTMSA-N campesterol 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](C)C(C)C)[C@@]1(C)CC2 SGNBVLSWZMBQTH-PODYLUTMSA-N 0.000 description 1
235000000431 campesterol Nutrition 0.000 description 1
229940041514 candida albicans extract Drugs 0.000 description 1
235000012000 cholesterol Nutrition 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
229910000388 diammonium phosphate Inorganic materials 0.000 description 1
235000019838 diammonium phosphate Nutrition 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
229910000397 disodium phosphate Inorganic materials 0.000 description 1
235000019800 disodium phosphate Nutrition 0.000 description 1
AJFXNBUVIBKWBT-UHFFFAOYSA-N disodium;boric acid;hydrogen borate Chemical compound [Na+].[Na+].OB(O)O.OB(O)O.OB(O)O.OB([O-])[O-] AJFXNBUVIBKWBT-UHFFFAOYSA-N 0.000 description 1
NBEMQPLNBYYUAZ-UHFFFAOYSA-N ethyl acetate;propan-2-one Chemical compound CC(C)=O.CCOC(C)=O NBEMQPLNBYYUAZ-UHFFFAOYSA-N 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
230000003152 gestagenic effect Effects 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
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 1
230000002906 microbiologic effect Effects 0.000 description 1
244000005700 microbiome Species 0.000 description 1
239000000203 mixture Substances 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
230000000877 morphologic effect Effects 0.000 description 1
239000003471 mutagenic agent Substances 0.000 description 1
231100000707 mutagenic chemical Toxicity 0.000 description 1
229920000151 polyglycol Polymers 0.000 description 1
239000010695 polyglycol Substances 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
239000000047 product Substances 0.000 description 1
238000010926 purge Methods 0.000 description 1
229940083492 sitosterols Drugs 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
NVIFVTYDZMXWGX-UHFFFAOYSA-N sodium metaborate Chemical compound [Na+].[O-]B=O NVIFVTYDZMXWGX-UHFFFAOYSA-N 0.000 description 1
241000894007 species Species 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
239000000080 wetting agent Substances 0.000 description 1
238000010626 work up procedure Methods 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
- C12P33/005—Degradation of the lateral chains at position 17
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Zoology (AREA)
Wood Science & Technology (AREA)
General Chemical & Material Sciences (AREA)
Microbiology (AREA)
Chemical Kinetics & Catalysis (AREA)
Biotechnology (AREA)
Biochemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
General Engineering & Computer Science (AREA)
Genetics & Genomics (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Micro-Organisms Or Cultivation Processes Thereof (AREA)

DD78209813A 1977-12-19 1978-12-15 Verfahren zur herstellung von 21-hydroxy-20-methylpregnanen DD139859A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19772757156 DE2757156A1 (de)	1977-12-19	1977-12-19	Verfahren zur herstellung von 21-hydroxy-20-methyl-pregnan-derivaten

Publications (1)

Publication Number	Publication Date
DD139859A5 true DD139859A5 (de)	1980-01-23

Family

ID=6026798

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD78209813A DD139859A5 (de)	1977-12-19	1978-12-15	Verfahren zur herstellung von 21-hydroxy-20-methylpregnanen

Country Status (12)

Country	Link
EP (1)	EP0002535B1 (fr)
JP (1)	JPS5581A (fr)
AT (1)	AT363625B (fr)
CS (1)	CS202517B2 (fr)
DD (1)	DD139859A5 (fr)
DE (2)	DE2757156A1 (fr)
DK (1)	DK144708C (fr)
GB (1)	GB2010276B (fr)
HU (1)	HU181505B (fr)
IE (1)	IE47691B1 (fr)
SU (1)	SU862830A3 (fr)
YU (1)	YU285578A (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4800072A (en) *	1988-01-14	1989-01-24	Rhone Poulenc, Inc.	Anhydrous cerous nitrate-ammonium nitrate complex and a process for its preparation from ceric ammonium nitrate
US10604544B2 (en) *	2015-08-07	2020-03-31	Intercept Pharmaceuticals, Inc.	Methods for preparation of bile acids and derivatives thereof
CN111651099A (zh)	2020-04-28	2020-09-11	北京载诚科技有限公司	一种触控装置
CN111596791A (zh)	2020-04-28	2020-08-28	北京载诚科技有限公司	一种触控面板

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3684657A (en) *	1970-05-11	1972-08-15	Searle & Co	Selective microbiological degradation of steroidal 17-alkyls
US3759791A (en) *	1970-12-10	1973-09-18	Searle & Co	Selective microbiological preparation of androst-4-ene-3,17-dione

1977
- 1977-12-19 DE DE19772757156 patent/DE2757156A1/de not_active Withdrawn
1978
- 1978-12-04 SU SU782691554A patent/SU862830A3/ru active
- 1978-12-06 YU YU02855/78A patent/YU285578A/xx unknown
- 1978-12-15 DE DE7878101711T patent/DE2861249D1/de not_active Expired
- 1978-12-15 DD DD78209813A patent/DD139859A5/de unknown
- 1978-12-15 EP EP78101711A patent/EP0002535B1/fr not_active Expired
- 1978-12-18 HU HU78SCHE665A patent/HU181505B/hu not_active IP Right Cessation
- 1978-12-18 AT AT0904778A patent/AT363625B/de not_active IP Right Cessation
- 1978-12-18 JP JP15502178A patent/JPS5581A/ja active Granted
- 1978-12-18 IE IE2486/78A patent/IE47691B1/en unknown
- 1978-12-19 CS CS788574A patent/CS202517B2/cs unknown
- 1978-12-19 DK DK570578A patent/DK144708C/da not_active IP Right Cessation
- 1978-12-19 GB GB7848989A patent/GB2010276B/en not_active Expired

Also Published As

Publication number	Publication date
HU181505B (en)	1983-10-28
IE782486L (en)	1979-06-19
EP0002535A3 (en)	1979-07-11
JPS6350000B2 (fr)	1988-10-06
YU285578A (en)	1982-10-31
DK570578A (da)	1979-06-20
JPS5581A (en)	1980-01-05
IE47691B1 (en)	1984-05-30
DE2861249D1 (en)	1981-12-10
GB2010276A (en)	1979-06-27
DK144708B (da)	1982-05-17
SU862830A3 (ru)	1981-09-07
EP0002535A2 (fr)	1979-06-27
DK144708C (da)	1982-10-11
DE2757156A1 (de)	1979-06-21
AT363625B (de)	1981-08-25
ATA904778A (de)	1981-01-15
CS202517B2 (en)	1981-01-30
GB2010276B (en)	1982-08-04
EP0002535B1 (fr)	1981-09-30

Publication	Publication Date	Title
DE2632677C2 (fr)	1988-06-16
DE3876769T2 (de)	1993-06-09	Mikrobiologische herstellung von 9-alpha-hydroxy-17-keto-steroiden.
EP0004913A1 (fr)	1979-10-31	Procédé de dégradation sélective de chaînes latérales de stéroides et de préparation des microorganismes mutants déficients bloqués appropriés et nouvelles souches de microorganismes
EP0225892B1 (fr)	1990-05-16	Procede de preparation de 4-androstene-3,17-dione et de 1,4-androstadiene-3,17-dione
EP0002535B1 (fr)	1981-09-30	Procédé de préparation de 21-hydroxy-20-méthyl-pregnanes
DE2534911C2 (de)	1985-04-18	Verfahren zur Herstellung von 5-Androsten-17-on-Derivaten
EP0014991B1 (fr)	1983-01-19	Procédé microbiologique de préparation de stéroides 7-alpha-hydroxylés
EP0027829B1 (fr)	1983-06-29	Procédé de préparation de 9-alpha-hydroxy-4-androstène-3,17-dione
US4212940A (en)	1980-07-15	Process for the preparation of 21-hydroxy-20-methylpregnane derivatives
EP0505514B1 (fr)	1996-05-22	PROCEDE DE PRODUCTION DE DERIVES DE $g(b)-CARBOLINE
EP0496845B1 (fr)	1997-01-08	Procede de production de 4-pregnen-3,20-dione et de ses derives
EP0227588B1 (fr)	1991-11-06	Procédé de préparation d'androst-4-ène-3,17-dione et d'androsta-1,4-diène-3,17-dione
EP0496846B1 (fr)	1997-05-07	Procede pour la fabrication de 17-oxosteroides
EP0496854B1 (fr)	2000-03-15	Procédé pour la preparation des DERIVES DE 20-METHYLE-5,7-PREGNADIENE-3$g(b),21-DIOL
DE2558090A1 (de)	1977-07-07	Verfahren zur herstellung von 4-androsten-3,17-dion-derivaten
WO1987005940A1 (fr)	1987-10-08	PROCEDE POUR LA PRODUCTION DE 17aalpha-HYDROXY-D-HOMO-1,4-PREGNADIENE-3,20-DIONE
CH625555A5 (fr)	1981-09-30
DE2850047A1 (de)	1980-10-09	Verfahren zur herstellung von 9 alpha -hydroxy-4-androsten-3,17-dion
DE2940285A1 (de)	1981-05-07	Verfahren zur herstellung von 11(alpha)-hydroxy-3-oxo-(delta)(pfeil hoch)1(pfeil hoch)(pfeil hoch),(pfeil hoch)(pfeil hoch)4(pfeil hoch)-steroiden
DE2715854A1 (de)	1978-10-19	Verfahren zur herstellung von 11alpha,21-dihydroxy-1,4-pregnadien- 3,20-dion-derivaten
DE2919984A1 (de)	1980-11-27	12 alpha -hydroxysteroide und deren herstellung
DE3023791A1 (de)	1982-01-21	Verfahren zur herstellung von 11 (beta) -hydroxysteroiden
DE2901563A1 (de)	1980-07-24	17 alpha -acyloxy-12 beta -hydroxy-4pregnen-3,20-dion-derivate und verfahren zu ihrer herstellung
DE2306529A1 (de)	1974-08-15	Neue 12 beta, 15 alpha-dihydroxysteroide
DE1088487B (de)	1960-09-08	Verfahren zur Herstellung neuer Halogenpregnanverbindungen