NO125889B - - Google Patents

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Info

Publication number: NO125889B
Authority: NO; Norway
Prior art keywords: dione; cholesterol; added; flasks; mycobacterium
Prior art date: 1965-10-22

Application number

NO16521966A

Other languages

English (en)

Norwegian (no)

Inventor

Waard W Van Der

Original Assignee

Koninklijke Gist Spiritus

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.)

1965-10-22

Filing date

1966-10-19

Publication date

1972-11-20

1966-10-19 Application filed by Koninklijke Gist Spiritus filed Critical Koninklijke Gist Spiritus

1972-11-20 Publication of NO125889B publication Critical patent/NO125889B/no

Links

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 claims description 58
235000012000 cholesterol Nutrition 0.000 claims description 29
150000003431 steroids Chemical class 0.000 claims description 20
238000000034 method Methods 0.000 claims description 18
239000003112 inhibitor Substances 0.000 claims description 15
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 claims description 13
AEMFNILZOJDQLW-UHFFFAOYSA-N androstenedione Natural products O=C1CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 AEMFNILZOJDQLW-UHFFFAOYSA-N 0.000 claims description 13
241000186359 Mycobacterium Species 0.000 claims description 12
229960005471 androstenedione Drugs 0.000 claims description 12
-1 3-sitosterol Chemical compound 0.000 claims description 10
241000187481 Mycobacterium phlei Species 0.000 claims description 8
244000005700 microbiome Species 0.000 claims description 8
229940055036 mycobacterium phlei Drugs 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims 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 claims description 6
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 claims description 5
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 claims description 5
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 claims description 5
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 claims description 5
NYOXRYYXRWJDKP-GYKMGIIDSA-N cholest-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)CCCC(C)C)[C@@]1(C)CC2 NYOXRYYXRWJDKP-GYKMGIIDSA-N 0.000 claims description 5
NYOXRYYXRWJDKP-UHFFFAOYSA-N cholestenone Natural products C1CC2=CC(=O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 NYOXRYYXRWJDKP-UHFFFAOYSA-N 0.000 claims description 5
230000002906 microbiologic effect Effects 0.000 claims description 5
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 claims description 5
235000016831 stigmasterol Nutrition 0.000 claims description 5
229940032091 stigmasterol Drugs 0.000 claims description 5
BFDNMXAIBMJLBB-UHFFFAOYSA-N stigmasterol Natural products CCC(C=CC(C)C1CCCC2C3CC=C4CC(O)CCC4(C)C3CCC12C)C(C)C BFDNMXAIBMJLBB-UHFFFAOYSA-N 0.000 claims description 5
230000009466 transformation Effects 0.000 claims description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
150000001441 androstanes Chemical class 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
239000011133 lead Substances 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
229920006395 saturated elastomer Polymers 0.000 claims description 3
229950005143 sitosterol Drugs 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
125000001931 aliphatic group Chemical group 0.000 claims description 2
229910052793 cadmium Inorganic materials 0.000 claims description 2
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims description 2
239000010941 cobalt Substances 0.000 claims description 2
229910017052 cobalt Inorganic materials 0.000 claims description 2
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
229910052759 nickel Inorganic materials 0.000 claims description 2
229910052711 selenium Inorganic materials 0.000 claims description 2
239000011669 selenium Substances 0.000 claims 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 18
239000002609 medium Substances 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 11
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
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 8
241000894006 Bacteria Species 0.000 description 8
239000000047 product Substances 0.000 description 8
238000011081 inoculation Methods 0.000 description 7
239000000203 mixture Substances 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
238000004809 thin layer chromatography Methods 0.000 description 6
239000000284 extract Substances 0.000 description 5
239000007788 liquid Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
229910052784 alkaline earth metal Inorganic materials 0.000 description 4
LGQLOGILCSXPEA-UHFFFAOYSA-L nickel sulfate Chemical compound [Ni+2].[O-]S([O-])(=O)=O LGQLOGILCSXPEA-UHFFFAOYSA-L 0.000 description 4
DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 description 3
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
241000187654 Nocardia Species 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229930182558 Sterol Natural products 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
229960003237 betaine Drugs 0.000 description 3
230000015556 catabolic process Effects 0.000 description 3
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 3
150000001875 compounds Chemical class 0.000 description 3
235000005822 corn Nutrition 0.000 description 3
229960003399 estrone Drugs 0.000 description 3
238000000855 fermentation Methods 0.000 description 3
230000004151 fermentation Effects 0.000 description 3
239000013067 intermediate product Substances 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
239000000243 solution Substances 0.000 description 3
150000003432 sterols Chemical class 0.000 description 3
235000003702 sterols Nutrition 0.000 description 3
239000000758 substrate Substances 0.000 description 3
239000008399 tap water Substances 0.000 description 3
235000020679 tap water Nutrition 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
238000005273 aeration Methods 0.000 description 2
239000003513 alkali Substances 0.000 description 2
150000001342 alkaline earth metals Chemical class 0.000 description 2
230000001195 anabolic effect Effects 0.000 description 2
230000008033 biological extinction Effects 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
QCUOBSQYDGUHHT-UHFFFAOYSA-L cadmium sulfate Chemical compound [Cd+2].[O-]S([O-])(=O)=O QCUOBSQYDGUHHT-UHFFFAOYSA-L 0.000 description 2
229940041514 candida albicans extract Drugs 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 2
BVTBRVFYZUCAKH-UHFFFAOYSA-L disodium selenite Chemical compound [Na+].[Na+].[O-][Se]([O-])=O BVTBRVFYZUCAKH-UHFFFAOYSA-L 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000001963 growth medium Substances 0.000 description 2
238000002955 isolation Methods 0.000 description 2
229940046892 lead acetate Drugs 0.000 description 2
229960004719 nandrolone Drugs 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
229910000363 nickel(II) sulfate Inorganic materials 0.000 description 2
238000000746 purification Methods 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
229960001471 sodium selenite Drugs 0.000 description 2
239000011781 sodium selenite Substances 0.000 description 2
235000015921 sodium selenite Nutrition 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000012138 yeast extract Substances 0.000 description 2
GWOSBUGZGFVDDS-LKGWFGLDSA-N (8s,9s,10r,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,7,8,9,11,12,14,15,16,17-decahydro-1h-cyclopenta[a]phenanthrene-3,6-dione Chemical compound C1C(=O)C2=CC(=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 GWOSBUGZGFVDDS-LKGWFGLDSA-N 0.000 description 1
IATKKATWPOVYCC-VMXHOPILSA-N (8s,9s,10r,13s,14s)-10,13-dimethyl-2,3,6,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthrene Chemical compound C1CC2=CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 IATKKATWPOVYCC-VMXHOPILSA-N 0.000 description 1
XUGISPSHIFXEHZ-UHFFFAOYSA-N 3beta-acetoxy-cholest-5-ene Natural products C1C=C2CC(OC(C)=O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 XUGISPSHIFXEHZ-UHFFFAOYSA-N 0.000 description 1
YEYCQJVCAMFWCO-UHFFFAOYSA-N 3beta-cholesteryl formate Natural products C1C=C2CC(OC=O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 YEYCQJVCAMFWCO-UHFFFAOYSA-N 0.000 description 1
QGXBDMJGAMFCBF-HLUDHZFRSA-N 5α-Androsterone Chemical compound C1[C@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC[C@H]21 QGXBDMJGAMFCBF-HLUDHZFRSA-N 0.000 description 1
239000005725 8-Hydroxyquinoline Substances 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
241000589151 Azotobacter Species 0.000 description 1
UCTLRSWJYQTBFZ-UHFFFAOYSA-N Dehydrocholesterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)CCCC(C)C)CCC33)C)C3=CC=C21 UCTLRSWJYQTBFZ-UHFFFAOYSA-N 0.000 description 1
QGXBDMJGAMFCBF-UHFFFAOYSA-N Etiocholanolone Natural products C1C(O)CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CCC21 QGXBDMJGAMFCBF-UHFFFAOYSA-N 0.000 description 1
241000589565 Flavobacterium Species 0.000 description 1
VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical compound [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
239000001888 Peptone Substances 0.000 description 1
108010080698 Peptones Proteins 0.000 description 1
241000589516 Pseudomonas Species 0.000 description 1
235000019764 Soybean Meal Nutrition 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
241000187747 Streptomyces Species 0.000 description 1
LGDAGYXJBDILKZ-UHFFFAOYSA-N [2-methyl-1,1-dioxo-3-(pyridin-2-ylcarbamoyl)-1$l^{6},2-benzothiazin-4-yl] 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 LGDAGYXJBDILKZ-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000008272 agar Substances 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
239000003098 androgen Substances 0.000 description 1
230000001548 androgenic effect Effects 0.000 description 1
229940061641 androsterone Drugs 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
XUGISPSHIFXEHZ-VEVYEIKRSA-N cholesteryl acetate Chemical compound C1C=C2C[C@@H](OC(C)=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 XUGISPSHIFXEHZ-VEVYEIKRSA-N 0.000 description 1
WLNARFZDISHUGS-MIXBDBMTSA-N cholesteryl hemisuccinate Chemical compound C1C=C2C[C@@H](OC(=O)CCC(O)=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 WLNARFZDISHUGS-MIXBDBMTSA-N 0.000 description 1
235000012343 cottonseed oil Nutrition 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000000593 degrading effect Effects 0.000 description 1
230000001627 detrimental effect Effects 0.000 description 1
238000007865 diluting Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003480 eluent Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
229940011871 estrogen Drugs 0.000 description 1
239000000262 estrogen Substances 0.000 description 1
230000001076 estrogenic effect Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000499 gel Substances 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
235000012054 meals Nutrition 0.000 description 1
239000000401 methanolic extract Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000004570 mortar (masonry) Substances 0.000 description 1
229910001453 nickel ion Inorganic materials 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000001477 organic nitrogen group Chemical group 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
229960003540 oxyquinoline Drugs 0.000 description 1
235000019319 peptone Nutrition 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
238000010298 pulverizing process Methods 0.000 description 1
MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
238000011218 seed culture Methods 0.000 description 1
229940091258 selenium supplement Drugs 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000004455 soybean meal Substances 0.000 description 1
241000894007 species Species 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
229960003604 testosterone Drugs 0.000 description 1
239000011573 trace mineral Substances 0.000 description 1
235000013619 trace mineral Nutrition 0.000 description 1
238000009423 ventilation Methods 0.000 description 1
QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 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

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)

NO16521966A 1965-10-22 1966-10-19 NO125889B (2)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
NL6513718A NL6513718A (2)	1965-10-22	1965-10-22

Publications (1)

Publication Number	Publication Date
NO125889B true NO125889B (2)	1972-11-20

Family

ID=19794437

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO16521966A NO125889B (2)	1965-10-22	1966-10-19

Country Status (13)

Country	Link
AT (1)	AT267774B (2)
BE (1)	BE688518A (2)
BR (1)	BR6683880D0 (2)
CH (1)	CH485689A (2)
DE (1)	DE1568932A1 (2)
DK (1)	DK119405B (2)
ES (1)	ES332381A1 (2)
GB (1)	GB1113887A (2)
IL (1)	IL26679A (2)
IT (1)	IT1143556B (2)
NL (1)	NL6513718A (2)
NO (1)	NO125889B (2)
SE (1)	SE322507B (2)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL189865C (nl) *	1976-10-22	1993-08-16	Upjohn Co	Werkwijze voor het bereiden van androst-4-een-3,17-dion en de daarbij toegepaste micro-organismen.
EP0322081B1 (en) *	1987-12-23	1992-12-16	Roussel-Uclaf	Microbiological preparation of 9-alpha-hydroxy-17-keto steroids
US5298398A (en) *	1987-12-23	1994-03-29	Gist-Brocades Nv	Preparation of 9-α-hydroxy-17-keto steroids using Mycobacterium species CBS 482.86

1965
- 1965-10-22 NL NL6513718A patent/NL6513718A/xx unknown
1966
- 1966-10-12 IL IL2667966A patent/IL26679A/xx unknown
- 1966-10-12 GB GB4560466A patent/GB1113887A/en not_active Expired
- 1966-10-18 DE DE19661568932 patent/DE1568932A1/de active Pending
- 1966-10-18 ES ES0332381A patent/ES332381A1/es not_active Expired
- 1966-10-19 BE BE688518D patent/BE688518A/xx not_active IP Right Cessation
- 1966-10-19 IT IT4225566A patent/IT1143556B/it active
- 1966-10-19 NO NO16521966A patent/NO125889B/no unknown
- 1966-10-19 DK DK541866A patent/DK119405B/da unknown
- 1966-10-20 CH CH1523266A patent/CH485689A/de not_active IP Right Cessation
- 1966-10-20 SE SE1426066A patent/SE322507B/xx unknown
- 1966-10-21 BR BR18388066A patent/BR6683880D0/pt unknown
- 1966-10-21 AT AT983666A patent/AT267774B/de active

Also Published As

Publication number	Publication date
SE322507B (2)	1970-04-13
NL6513718A (2)	1967-04-24
DK119405B (da)	1970-12-28
ES332381A1 (es)	1967-08-01
AT267774B (de)	1969-01-10
BR6683880D0 (pt)	1973-12-04
IT1143556B (it)	1986-10-22
GB1113887A (en)	1968-05-15
CH485689A (de)	1970-02-15
BE688518A (2)	1967-04-19
DE1568932A1 (de)	1970-06-18
IL26679A (en)	1970-07-19

Publication	Publication Date	Title
US2756179A (en)	1956-07-24	Production of delta 1 bonds in the a ring of the cyclopentanopolyhydrophenanthrene nucleus by streptomyces lavendulae
PL109912B1 (en)	1980-06-30	Method of producing 9 alpha-hydroxyandrostendione
US3684656A (en)	1972-08-15	Process for the micro-biological preparation of steroids
Wix et al.	1968	Inhibition of steroid nucleus degradation in mycobacterial transformations
Saunders et al.	1986	Microbial transformation of crude fenugreek steroids
Turfitt	1946	The microbiological degradation of steroids: 3. Oxidation of hydroxy-steroids to keto-derivatives by Proactinomyces spp
JPH022395A (ja)	1990-01-08	９α―ヒドロキシ―１７―ケトステロイドの微生物学的製法
US4397947A (en)	1983-08-09	Microbial process for 9α-hydroxylation of steroids
US4255344A (en)	1981-03-10	9-α-Hydroxy steroids
US2960436A (en)	1960-11-15	Synthesis of steroids by diplodia natalensis
US2968595A (en)	1961-01-17	Oxygenation of steroids by rhizoctonia and sclerotium
Singh et al.	1967	Mechanism of side-chain degradation of C21 steroids by spores of Septomyxa affinis
Charney et al.	1962	Microbiological transformation of steroids—XI: the action of corynebacterium simplex on non-corticoid steroid substrates
US3080298A (en)	1963-03-05	Method of 9alpha-hydroxylating steroids
US3340278A (en)	1967-09-05	5(10), 7-estradiene-3, 17-dione and the process for the production thereof
DE2660114B1 (de)	1980-03-20	Verfahren zur Herstellung neuer 7alpha beta-Methylhexahydro-1,(5)-indan(di)on-Verbindungen unter Verwendung von Mikroorganismus-Mutanten
CH638563A5 (en)	1983-09-30	Process for the preparation of a mixture of androsta-1,4-diene-3,17-dione and androst-4-ene-3,17-dione
US3487907A (en)	1970-01-06	Process for the microbiological preparation of steroids having no carbonaceous substituent in the 17-position
Zohri et al.	1999	Progesterone transformations by three species of Humicola
US2992973A (en)	1961-07-18	Dehydrogenation of steroids by azotobacter microorganisms
EP0114984B1 (de)	1987-10-21	Verfahren zur Herstellung von 3,11-alpha-Dihydroxy-1,3,5(10)-östratrien-Derivaten
Miller	1972	The inhibition of microbial steroid D-ring lactonization by high levels of progesterone
US3297687A (en)	1967-01-10	Method of preparing 1, 2-disubstituted steroids and products resulting therefrom
US3575810A (en)	1971-04-20	Method for removal of side chain of sapogenins
US4333880A (en)	1982-06-08	3-Oxo-pregna-1,14,17-trien-20-carboxylates and process