CH625554A5 - - Google Patents

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Info

Publication number: CH625554A5
Authority: CH; Switzerland
Prior art keywords: general formula; derivatives; group; sterols; side chain
Prior art date: 1975-12-19

Application number

CH1586176A

Other languages

German (de)

English (en)

Inventor

Alfred Dr Weber

Mario Dr Kennecke

Rudolf Dr Mueller

Ulrich Dr Eder

Rudolf Prof Dr Wiechert

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.)

1975-12-19

Filing date

1976-12-16

Publication date

1981-09-30

1976-12-16 Application filed by Schering Ag filed Critical Schering Ag

1981-09-30 Publication of CH625554A5 publication Critical patent/CH625554A5/de

Links

229930182558 Sterol Natural products 0.000 claims description 19
150000003432 sterols Chemical class 0.000 claims description 19
235000003702 sterols Nutrition 0.000 claims description 19
230000015556 catabolic process Effects 0.000 claims description 11
238000006731 degradation reaction Methods 0.000 claims description 11
244000005700 microbiome Species 0.000 claims description 11
238000000034 method Methods 0.000 claims description 10
238000006243 chemical reaction Methods 0.000 claims description 7
-1 1,2-methylene group Chemical group 0.000 claims description 6
150000001875 compounds Chemical class 0.000 claims description 5
238000000855 fermentation Methods 0.000 claims description 5
230000004151 fermentation Effects 0.000 claims description 5
241000193830 Bacillus <bacterium> Species 0.000 claims description 4
241001467578 Microbacterium Species 0.000 claims description 4
241000586779 Protaminobacter Species 0.000 claims description 4
241000187747 Streptomyces Species 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
241000186146 Brevibacterium Species 0.000 claims description 3
241000186359 Mycobacterium Species 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
241000186063 Arthrobacter Species 0.000 claims description 2
239000004215 Carbon black (E152) Substances 0.000 claims description 2
MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical class 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 claims description 2
OSVMTWJCGUFAOD-KZQROQTASA-N formestane Chemical class 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 2
229930195733 hydrocarbon Natural products 0.000 claims description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
239000000758 substrate Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
241000187488 Mycobacterium sp. Species 0.000 description 5
239000007858 starting material Substances 0.000 description 5
241000187480 Mycobacterium smegmatis Species 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
150000003431 steroids Chemical class 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
241000187481 Mycobacterium phlei Species 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
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 3
238000001035 drying Methods 0.000 description 3
238000004945 emulsification Methods 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
230000002906 microbiologic effect Effects 0.000 description 3
229940055036 mycobacterium phlei Drugs 0.000 description 3
235000015097 nutrients Nutrition 0.000 description 3
239000003921 oil Substances 0.000 description 3
229920000136 polysorbate Polymers 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
239000002904 solvent Substances 0.000 description 3
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 2
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
108090000790 Enzymes Proteins 0.000 description 2
102000004190 Enzymes Human genes 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
AEMFNILZOJDQLW-UHFFFAOYSA-N androstenedione Natural products O=C1CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 AEMFNILZOJDQLW-UHFFFAOYSA-N 0.000 description 2
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 description 2
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 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
238000004587 chromatography analysis Methods 0.000 description 2
230000000593 degrading effect Effects 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
239000005457 ice water Substances 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
239000000203 mixture Substances 0.000 description 2
229940068065 phytosterols Drugs 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
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 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
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
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-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
OILXMJHPFNGGTO-MPVBJYOVSA-N Brassicasterin Natural products CC(C)[C@@H](C)C=C[C@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@@H]3CC[C@@]12C OILXMJHPFNGGTO-MPVBJYOVSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 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
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
241001491638 Corallina Species 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-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
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
241000186367 Mycobacterium avium Species 0.000 description 1
241000186365 Mycobacterium fortuitum Species 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 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
239000000654 additive Substances 0.000 description 1
238000005273 aeration Methods 0.000 description 1
SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
230000001195 anabolic effect Effects 0.000 description 1
230000001548 androgenic effect Effects 0.000 description 1
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 1
229960005471 androstenedione Drugs 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
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 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
OILXMJHPFNGGTO-ZAUYPBDWSA-N brassicasterol 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](C)C(C)C)[C@@]1(C)CC2 OILXMJHPFNGGTO-ZAUYPBDWSA-N 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 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
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
238000012993 chemical processing Methods 0.000 description 1
235000012000 cholesterol Nutrition 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 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
230000000694 effects Effects 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000002430 hydrocarbons Chemical group 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
238000005907 ketalization reaction Methods 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
229910052808 lithium carbonate Inorganic materials 0.000 description 1
VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
235000019796 monopotassium phosphate Nutrition 0.000 description 1
238000006053 organic reaction Methods 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
229920000151 polyglycol Polymers 0.000 description 1
239000010695 polyglycol Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000007017 scission Effects 0.000 description 1
KZJWDPNRJALLNS-VJSFXXLFSA-N sitosterol Chemical class 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
229940083492 sitosterols Drugs 0.000 description 1
150000003385 sodium Chemical class 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 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
238000003756 stirring Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
BPLKQGGAXWRFOE-UHFFFAOYSA-M trimethylsulfoxonium iodide Chemical compound [I-].C[S+](C)(C)=O BPLKQGGAXWRFOE-UHFFFAOYSA-M 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000012138 yeast extract 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- 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
- C07J1/0018—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa
- C07J1/0022—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa the substituent being an OH group free esterified or etherified
- C07J1/0025—Esters
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class
- C07J53/002—Carbocyclic rings fused
- C07J53/004—3 membered carbocyclic rings
- C07J53/005—3 membered carbocyclic rings in position 12
- 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
- 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
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/83—Arthrobacter
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/832—Bacillus
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/84—Brevibacterium
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/863—Mycobacterium
- Y10S435/866—Mycobacterium smegmatis
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/872—Nocardia
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/886—Streptomyces

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Microbiology (AREA)
Biochemistry (AREA)
General Engineering & Computer Science (AREA)
Biotechnology (AREA)
Genetics & Genomics (AREA)
Medicinal Chemistry (AREA)
Endocrinology (AREA)
Diabetes (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Steroid Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH1586176A 1975-12-19 1976-12-16 CH625554A5 (es)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2558090A DE2558090C2 (de)	1975-12-19	1975-12-19	Verfahren zur Herstellung von 4-Androsten-3,17-dion-Derivaten

Publications (1)

Publication Number	Publication Date
CH625554A5 true CH625554A5 (es)	1981-09-30

Family

ID=5965332

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1586176A CH625554A5 (es)	1975-12-19	1976-12-16

Country Status (14)

Country	Link
US (1)	US4100026A (es)
JP (1)	JPS5294495A (es)
AT (1)	AT367094B (es)
BE (1)	BE849559A (es)
CH (1)	CH625554A5 (es)
CS (1)	CS187347B2 (es)
DD (2)	DD134107A5 (es)
DE (1)	DE2558090C2 (es)
DK (1)	DK139269C (es)
FR (1)	FR2335524A1 (es)
GB (1)	GB1571912A (es)
HU (1)	HU183021B (es)
IE (1)	IE44516B1 (es)
NL (1)	NL7614036A (es)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4212940A (en) *	1978-12-19	1980-07-15	Schering Aktiengesellschaft	Process for the preparation of 21-hydroxy-20-methylpregnane derivatives
WO1999007381A1 (en) *	1997-08-11	1999-02-18	Weider Nutrition International, Inc.	Compositions and treatments to reduce side effects of administration of androgenic testosterone precursors

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1092145A (en) *	1964-06-02	1967-11-22	Noda Inst For Scientific Res	Microbiological conversion of steroids
NL6705450A (es) *	1965-10-22	1968-10-21
US3684657A (en) *	1970-05-11	1972-08-15	Searle & Co	Selective microbiological degradation of steroidal 17-alkyls
DE2046640C3 (de) *	1970-09-14	1973-10-18	Schering Ag	Verfahren zur Herstellung von Delta hoch 4 -3-Oxo-l alpha-methyl·Steroiden
US3759791A (en) *	1970-12-10	1973-09-18	Searle & Co	Selective microbiological preparation of androst-4-ene-3,17-dione

1975
- 1975-12-19 DE DE2558090A patent/DE2558090C2/de not_active Expired
1976
- 1976-12-16 CH CH1586176A patent/CH625554A5/de not_active IP Right Cessation
- 1976-12-16 DK DK566376A patent/DK139269C/da not_active IP Right Cessation
- 1976-12-17 DD DD76204018A patent/DD134107A5/xx unknown
- 1976-12-17 AT AT0935876A patent/AT367094B/de not_active IP Right Cessation
- 1976-12-17 BE BE173401A patent/BE849559A/xx not_active IP Right Cessation
- 1976-12-17 HU HU76SCHE587A patent/HU183021B/hu not_active IP Right Cessation
- 1976-12-17 US US05/751,677 patent/US4100026A/en not_active Expired - Lifetime
- 1976-12-17 NL NL7614036A patent/NL7614036A/xx not_active Application Discontinuation
- 1976-12-17 CS CS768343A patent/CS187347B2/cs unknown
- 1976-12-17 DD DD7600196439A patent/DD129333A5/xx unknown
- 1976-12-20 GB GB53147/76A patent/GB1571912A/en not_active Expired
- 1976-12-20 IE IE2787/76A patent/IE44516B1/en unknown
- 1976-12-20 FR FR7638310A patent/FR2335524A1/fr active Granted
- 1976-12-20 JP JP15412876A patent/JPS5294495A/ja active Granted

Also Published As

Publication number	Publication date
DE2558090A1 (de)	1977-07-07
IE44516B1 (en)	1981-12-30
BE849559A (fr)	1977-06-17
CS187347B2 (en)	1979-01-31
JPS615716B2 (es)	1986-02-20
FR2335524A1 (fr)	1977-07-15
DD134107A5 (de)	1979-02-07
IE44516L (en)	1977-06-19
FR2335524B1 (es)	1980-09-12
DE2558090C2 (de)	1985-05-30
HU183021B (en)	1984-04-28
DK566376A (da)	1977-06-20
DK139269B (da)	1979-01-22
NL7614036A (nl)	1977-06-21
DK139269C (da)	1979-07-09
ATA935876A (de)	1981-10-15
DD129333A5 (de)	1978-01-11
GB1571912A (en)	1980-07-23
JPS5294495A (en)	1977-08-09
US4100026A (en)	1978-07-11
AT367094B (de)	1982-05-25

Legal Events

Date	Code	Title	Description
1993-08-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE2632677C2 (es)	1988-06-16
CH622532A5 (es)	1981-04-15
EP0225892B1 (de)	1990-05-16	Verfahren zur herstellung von 4-androsten-3,17-dion und 1,4-androstadien-3,17-dion
CH624415A5 (es)	1981-07-31
CH625554A5 (es)	1981-09-30
EP0002535B1 (de)	1981-09-30	Verfahren zur Herstellung von 21-Hydroxy-20-methyl-pregnan-Derivaten
CH625555A5 (es)	1981-09-30
DE1904544C3 (de)	1978-05-18	Verfahren zur mikrobiologischen Umwandlung von 3 ß-Hydroxy-5,6- epoxysteroiden in 6-Hydroxy-3-KetoA<·4 -Steroide
EP0227588B1 (de)	1991-11-06	Verfahren zur Herstellung von 4-Androsten-3, 17-dion und 1,4-Androstadien-3,17-dion
EP0139907B1 (de)	1991-02-06	Verfahren zur Herstellung von Estran-Derivaten
EP0114984B1 (de)	1987-10-21	Verfahren zur Herstellung von 3,11-alpha-Dihydroxy-1,3,5(10)-östratrien-Derivaten
DE2061183A1 (de)	1971-06-24	Neue Steroide der Pregnanreihe
WO1992003572A1 (de)	1992-03-05	Verfahren zur herstellung von 17-oxosteroiden
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
DE2901563A1 (de)	1980-07-24	17 alpha -acyloxy-12 beta -hydroxy-4pregnen-3,20-dion-derivate und verfahren zu ihrer herstellung