CS200517B2 - Process for preparing derivatives of androstan-17-one or androsten-17-one - Google Patents
Process for preparing derivatives of androstan-17-one or androsten-17-one Download PDFInfo
- Publication number
- CS200517B2 CS200517B2 CS774682A CS468277A CS200517B2 CS 200517 B2 CS200517 B2 CS 200517B2 CS 774682 A CS774682 A CS 774682A CS 468277 A CS468277 A CS 468277A CS 200517 B2 CS200517 B2 CS 200517B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- sterol
- derivatives
- culture
- hydrogen atom
- androsten
- Prior art date
Links
- MNOAOFLIFDRILH-QAGGRKNESA-N (8r,9s,10r,13s,14s)-10,13-dimethyl-1,2,3,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one Chemical compound C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 MNOAOFLIFDRILH-QAGGRKNESA-N 0.000 title claims description 4
- YJDYCULVYZDESB-HKQXQEGQSA-N (5r,8r,9s,10s,13s,14s)-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one Chemical class C1CCC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC[C@H]21 YJDYCULVYZDESB-HKQXQEGQSA-N 0.000 title description 6
- 238000004519 manufacturing process Methods 0.000 title description 3
- 229930182558 Sterol Natural products 0.000 claims abstract description 21
- 235000003702 sterols Nutrition 0.000 claims abstract description 21
- 150000003432 sterols Chemical class 0.000 claims abstract description 20
- 244000005700 microbiome Species 0.000 claims abstract description 13
- 238000000855 fermentation Methods 0.000 claims abstract description 9
- 230000004151 fermentation Effects 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- 125000002328 sterol group Chemical group 0.000 claims abstract description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 14
- 238000006731 degradation reaction Methods 0.000 claims description 12
- 230000015556 catabolic process Effects 0.000 claims description 11
- 241000186359 Mycobacterium Species 0.000 claims description 7
- 230000000593 degrading effect Effects 0.000 claims description 7
- 241001467578 Microbacterium Species 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- YJDYCULVYZDESB-HQEMIIEJSA-N (8r,9s,10s,13s,14s)-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one Chemical compound C1CCC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC21 YJDYCULVYZDESB-HQEMIIEJSA-N 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- 241000193830 Bacillus <bacterium> Species 0.000 claims description 3
- 241000586779 Protaminobacter Species 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 241000186063 Arthrobacter Species 0.000 claims description 2
- 241000187747 Streptomyces Species 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
- 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 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- -1 stagmasterol Chemical compound 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000000758 substrate Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 241000187488 Mycobacterium sp. Species 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 235000012000 cholesterol Nutrition 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000011534 incubation Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000012043 crude product Substances 0.000 description 5
- 150000003431 steroids Chemical class 0.000 description 5
- 239000005909 Kieselgur Substances 0.000 description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- 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 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RMTJHEFQBGZUMY-JDZMIXGTSA-N C(C)OC(C)OC1CC2=CC[C@H]3[C@@H]4CC[C@H]([C@@H](CCCC(C)C)C)[C@]4(CC[C@@H]3[C@]2(CC1)C)C Chemical compound C(C)OC(C)OC1CC2=CC[C@H]3[C@@H]4CC[C@H]([C@@H](CCCC(C)C)C)[C@]4(CC[C@@H]3[C@]2(CC1)C)C RMTJHEFQBGZUMY-JDZMIXGTSA-N 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 239000002841 Lewis acid Substances 0.000 description 3
- 241000187481 Mycobacterium phlei Species 0.000 description 3
- 238000005273 aeration Methods 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
- 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 3
- 229960005471 androstenedione Drugs 0.000 description 3
- AEMFNILZOJDQLW-UHFFFAOYSA-N androstenedione Natural products O=C1CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 AEMFNILZOJDQLW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 150000007517 lewis acids Chemical class 0.000 description 3
- 229940055036 mycobacterium phlei Drugs 0.000 description 3
- 229940068065 phytosterols Drugs 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 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
- 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 2
- 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 2
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- IOFPEFHYDZRGPP-VQVGGTNESA-N 2-[(6R)-6-[(8S,9S,10R,13R,14S,17R)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylheptoxy]ethanol Chemical compound OCCOCC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4CCCC[C@]4(C)[C@H]3CC[C@]12C IOFPEFHYDZRGPP-VQVGGTNESA-N 0.000 description 2
- 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 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- 241000186146 Brevibacterium Species 0.000 description 2
- WRJWTONJZMASNO-RVIAGLLESA-N COC(C)OC1CC2=CC[C@H]3[C@@H]4CC[C@H]([C@@H](CCCC(C)C)C)[C@]4(CC[C@@H]3[C@]2(CC1)C)C Chemical compound COC(C)OC1CC2=CC[C@H]3[C@@H]4CC[C@H]([C@@H](CCCC(C)C)C)[C@]4(CC[C@@H]3[C@]2(CC1)C)C WRJWTONJZMASNO-RVIAGLLESA-N 0.000 description 2
- 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 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 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 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000187480 Mycobacterium smegmatis Species 0.000 description 2
- 241000187654 Nocardia Species 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- LGJMUZUPVCAVPU-UHFFFAOYSA-N beta-Sitostanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 LGJMUZUPVCAVPU-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 235000000431 campesterol Nutrition 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- KLKFAASOGCDTDT-UHFFFAOYSA-N ethoxymethoxyethane Chemical compound CCOCOCC KLKFAASOGCDTDT-UHFFFAOYSA-N 0.000 description 2
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 2
- 235000019796 monopotassium phosphate Nutrition 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 238000006053 organic reaction Methods 0.000 description 2
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 235000015500 sitosterol Nutrition 0.000 description 2
- 229940083492 sitosterols Drugs 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 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 2
- 235000016831 stigmasterol Nutrition 0.000 description 2
- 229940032091 stigmasterol Drugs 0.000 description 2
- 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 2
- 239000000126 substance Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- ZGXZEJFIDOJWOU-USXKJRLASA-N (8S,9S,10R,13R,14S,17R)-3-(2-methoxyethoxymethoxy)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene Chemical compound COCCOCOC1CC[C@]2(C)[C@H]3CC[C@]4(C)[C@H](CC[C@H]4[C@@H]3CC=C2C1)[C@H](C)CCCC(C)C ZGXZEJFIDOJWOU-USXKJRLASA-N 0.000 description 1
- XOEORPJNZNTSTE-SYAJIYQZSA-N (8S,9S,10R,13S,14S)-10-methyl-13-prop-2-ynyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene Chemical compound C(#C)C[C@@]12CCC[C@H]1[C@@H]1CC=C3CCCC[C@]3(C)[C@H]1CC2 XOEORPJNZNTSTE-SYAJIYQZSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 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 1
- DBPWSSGDRRHUNT-CEGNMAFCSA-N 17α-hydroxyprogesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)C)(O)[C@@]1(C)CC2 DBPWSSGDRRHUNT-CEGNMAFCSA-N 0.000 description 1
- CYEZXDVLBGFROE-UHFFFAOYSA-N 2,4-Dihydroxy-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C(O)=C1 CYEZXDVLBGFROE-UHFFFAOYSA-N 0.000 description 1
- TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical class C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- IOJKSDQZWPLHKY-KZSQEHGRSA-N COCOC1CC2=CC[C@H]3[C@@H]4CC[C@H]([C@@H](CCCC(C)C)C)[C@]4(CC[C@@H]3[C@]2(CC1)C)C Chemical compound COCOC1CC2=CC[C@H]3[C@@H]4CC[C@H]([C@@H](CCCC(C)C)C)[C@]4(CC[C@@H]3[C@]2(CC1)C)C IOJKSDQZWPLHKY-KZSQEHGRSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-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
- 241000193386 Lysinibacillus sphaericus Species 0.000 description 1
- 241000186367 Mycobacterium avium Species 0.000 description 1
- 241000186365 Mycobacterium fortuitum Species 0.000 description 1
- 238000006036 Oppenauer oxidation reaction Methods 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 241000936695 Streptomyces gardneri Species 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- WLXDNZNRANJXCS-UHFFFAOYSA-N [B].[F].[F].[F] Chemical compound [B].[F].[F].[F] WLXDNZNRANJXCS-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction 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
- 239000012267 brine Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 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
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 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
- SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical compound [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 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
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 230000002124 endocrine Effects 0.000 description 1
- QGXBDMJGAMFCBF-LUJOEAJASA-N epiandrosterone 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-LUJOEAJASA-N 0.000 description 1
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical group CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 1
- CHNXZKVNWQUJIB-CEGNMAFCSA-N ethisterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 CHNXZKVNWQUJIB-CEGNMAFCSA-N 0.000 description 1
- 229960000445 ethisterone Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 238000001914 filtration Methods 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
- 238000010438 heat treatment Methods 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 230000003054 hormonal effect Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 229960002899 hydroxyprogesterone Drugs 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical group COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 229960003604 testosterone Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 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
- 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
- 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
-
- 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
- C07J1/0033—Androstane derivatives substituted in position 17 alfa and 17 beta
- C07J1/0037—Androstane derivatives substituted in position 17 alfa and 17 beta the substituent in position 17 alfa being a saturated hydrocarbon group
-
- 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
- C07J1/0033—Androstane derivatives substituted in position 17 alfa and 17 beta
- C07J1/004—Androstane derivatives substituted in position 17 alfa and 17 beta the substituent in position 17 alfa being an unsaturated hydrocarbon group
- C07J1/0048—Alkynyl derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Zoology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Steroid Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS785917A CS200518B2 (cs) | 1976-07-16 | 1978-09-13 | Způsob výroby androslanových derivátů |
| CS785919A CS200520B2 (cs) | 1976-07-16 | 1978-09-13 | Způsob výroby androstan-17-onových derivátů |
| CS785918A CS200519B2 (cs) | 1976-07-16 | 1978-09-13 | Způsob výroby androstanových derivátů |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762632677 DE2632677A1 (de) | 1976-07-16 | 1976-07-16 | Verfahren zur herstellung von androstan-17-on-derivaten und deren verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS200517B2 true CS200517B2 (en) | 1980-09-15 |
Family
ID=5983514
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS774682A CS200517B2 (en) | 1976-07-16 | 1977-07-13 | Process for preparing derivatives of androstan-17-one or androsten-17-one |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4179336A (https=) |
| JP (1) | JPS5315493A (https=) |
| AT (1) | AT363196B (https=) |
| BE (1) | BE856860A (https=) |
| CH (3) | CH627190A5 (https=) |
| CS (1) | CS200517B2 (https=) |
| DD (4) | DD136141A5 (https=) |
| DE (1) | DE2632677A1 (https=) |
| DK (1) | DK142372C (https=) |
| FR (4) | FR2365588A1 (https=) |
| GB (1) | GB1585786A (https=) |
| HU (4) | HU182790B (https=) |
| IE (1) | IE45304B1 (https=) |
| IT (1) | IT1077339B (https=) |
| NL (1) | NL7706638A (https=) |
| SE (1) | SE440779B (https=) |
| SU (1) | SU980628A3 (https=) |
| YU (1) | YU164277A (https=) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55148083A (en) * | 1979-05-04 | 1980-11-18 | Mitsubishi Chem Ind Ltd | Microorganism |
| JPS55150893A (en) * | 1979-05-11 | 1980-11-25 | Mitsubishi Chem Ind Ltd | Novel microorganism |
| JPS578794A (en) * | 1980-06-17 | 1982-01-18 | Mitsubishi Chem Ind Ltd | Preparation of androstane-type steroid |
| US4755463A (en) * | 1982-05-25 | 1988-07-05 | Wisconsin Alumni Research Foundation | Process for preparing steroids |
| US4444884A (en) * | 1982-05-25 | 1984-04-24 | Wisconsin Alumni Research Foundation | Process for preparing steroids |
| EP0738703B1 (en) * | 1995-02-28 | 2002-05-22 | Nippon Shokubai Co., Ltd. | Acrylic acid derivatives, method for preparing the acrylic acid derivatives, and acrylic acid polymers |
| TR201907313T4 (tr) * | 2003-05-23 | 2019-06-21 | Nektar Therapeutics | İki PEG zinciri içeren PEG türevleri. |
| CN102656153B (zh) * | 2009-10-29 | 2015-02-18 | 延世大学校产学协力团 | 新型血管渗漏阻断剂 |
| WO2012116290A2 (en) | 2011-02-25 | 2012-08-30 | Washington University | Neuroactive 17(20)-z-vinylcyano-substituted steroids, prodrugs thereof, and methods of treatment using same |
| CN119192266A (zh) | 2011-10-14 | 2024-12-27 | 萨奇治疗股份有限公司 | 3,3-二取代的19-去甲孕甾烷化合物、组合物、及其用途 |
| MX365644B (es) | 2012-12-18 | 2019-06-10 | Univ Washington | Esteroides neuroactivos sustituidos con 19-alcoxi-17, profarmacos de los mismos, y metodos de tratamiento usando los mismos. |
| EP2956466A4 (en) | 2013-02-15 | 2016-11-02 | Univ Washington | NEUROACTIVE ENANTIOMERS 15, 16 AND 17 SUBSTITUTED STEROIDS AS MODULATORS FOR GABA-A RECEPTORS |
| US9512170B2 (en) | 2013-03-01 | 2016-12-06 | Washington University | Neuroactive 13, 17-substituted steroids as modulators for GABA type-A receptors |
| US9365502B2 (en) | 2013-03-11 | 2016-06-14 | Washington University | Neuroactive substituted cyclopenta[b]phenanthrenes as modulators for GABA type-A receptors |
| US9562026B2 (en) | 2013-03-14 | 2017-02-07 | Washington University | Neuroactive substituted cyclopent[a]anthracenes as modulators for GABA type-A receptors |
| WO2014169831A1 (en) | 2013-04-17 | 2014-10-23 | Sage Therapeutics, Inc. | 19-nor c3,3-disubstituted c21-c-bound heteroaryl steroids and methods of use thereof |
| JP6470258B2 (ja) | 2013-04-17 | 2019-02-13 | セージ セラピューティクス， インコーポレイテッド | １９−ノルｃ３，３−ジ置換ｃ２１−ｎ−ピラゾリルステロイドおよびその使用方法 |
| ES2807264T3 (es) | 2013-04-17 | 2021-02-22 | Sage Therapeutics Inc | Esteroides neuroactivos 19-nor para métodos de tratamiento |
| WO2014169836A1 (en) | 2013-04-17 | 2014-10-23 | Sage Therapeutics, Inc. | 19-nor neuroactive steroids and methods of use thereof |
| WO2015010054A2 (en) | 2013-07-19 | 2015-01-22 | Sage Therapeutics, Inc. | Neuroactive steroids, compositions, and uses thereof |
| ES2848823T3 (es) | 2013-08-23 | 2021-08-12 | Sage Therapeutics Inc | Esteroides neuroactivos, composiciones y usos de los mismos |
| WO2015195962A1 (en) | 2014-06-18 | 2015-12-23 | Sage Therapeutics, Inc. | Neuroactive steroids, compositions, and uses thereof |
| ME03809B (me) | 2014-10-16 | 2021-04-20 | Sage Therapeutics Inc | KOMPOZICIJE I POSTUPCI ZA LEČENJE POREMEĆAJA CNS-a |
| US10577390B2 (en) | 2014-10-16 | 2020-03-03 | Sage Therapeutics, Inc. | Compositions and methods for treating CNS disorders |
| WO2016082789A1 (en) | 2014-11-27 | 2016-06-02 | Sage Therapeutics, Inc. | Compositions and methods for treating cns disorders |
| WO2016123056A1 (en) | 2015-01-26 | 2016-08-04 | Sage Therapeutics, Inc. | Compositions and methods for treating cns disorders |
| EP4155314A1 (en) | 2015-02-20 | 2023-03-29 | Sage Therapeutics, Inc. | Neuroactive steroids, compositions, and uses thereof |
| MA45599A (fr) | 2016-07-11 | 2019-05-15 | Sage Therapeutics Inc | Stéroïdes neuroactifs substitués en c17, c20 et c21 et leurs procédés d'utilisation |
| US20190233465A1 (en) | 2016-07-11 | 2019-08-01 | Sage Therapeutics, Inc. | C7, c12, and c16 substituted neuroactive steroids and their methods of use |
| CR20240234A (es) | 2019-05-31 | 2024-07-09 | Sage Therapeutics Inc | ESTEROIDES NEUROACTIVOS Y COMPOSICIONES DE ESTOS (Divisional 2021-629) |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3451892A (en) * | 1965-10-19 | 1969-06-24 | Schering Corp | Process for the preparation of steroidal compounds |
| NL6705450A (https=) * | 1965-10-22 | 1968-10-21 | ||
| 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 |
| US3738983A (en) * | 1971-08-06 | 1973-06-12 | Searle & Co | Process for the preparation of 3-(3beta,17beta-dihydroxyandrost-5-en-17alpha-yl) propionic acid gamma-lactone |
| DE2534911C2 (de) * | 1975-08-01 | 1985-04-18 | Schering AG, 1000 Berlin und 4709 Bergkamen | Verfahren zur Herstellung von 5-Androsten-17-on-Derivaten |
-
1976
- 1976-07-16 DE DE19762632677 patent/DE2632677A1/de active Granted
-
1977
- 1977-06-16 NL NL7706638A patent/NL7706638A/xx not_active Application Discontinuation
- 1977-07-01 YU YU01642/77A patent/YU164277A/xx unknown
- 1977-07-06 US US05/813,391 patent/US4179336A/en not_active Expired - Lifetime
- 1977-07-12 CH CH861377A patent/CH627190A5/de not_active IP Right Cessation
- 1977-07-13 AT AT0504677A patent/AT363196B/de not_active IP Right Cessation
- 1977-07-13 CS CS774682A patent/CS200517B2/cs unknown
- 1977-07-13 IE IE1456/77A patent/IE45304B1/en unknown
- 1977-07-14 DD DD77206205A patent/DD136141A5/xx unknown
- 1977-07-14 DD DD7700200065A patent/DD132439A5/xx not_active IP Right Cessation
- 1977-07-14 DD DD77206210A patent/DD137235A5/xx unknown
- 1977-07-14 SE SE7708192A patent/SE440779B/xx not_active IP Right Cessation
- 1977-07-14 DD DD77206207A patent/DD136142A5/xx unknown
- 1977-07-15 HU HU8019A patent/HU182790B/hu unknown
- 1977-07-15 HU HU8020A patent/HU182681B/hu unknown
- 1977-07-15 IT IT25807/77A patent/IT1077339B/it active
- 1977-07-15 HU HU8018A patent/HU182789B/hu unknown
- 1977-07-15 JP JP8493277A patent/JPS5315493A/ja active Granted
- 1977-07-15 SU SU772502698A patent/SU980628A3/ru active
- 1977-07-15 BE BE179384A patent/BE856860A/xx not_active IP Right Cessation
- 1977-07-15 HU HU77SCHE614A patent/HU179344B/hu not_active IP Right Cessation
- 1977-07-15 DK DK323677A patent/DK142372C/da not_active IP Right Cessation
- 1977-07-15 GB GB29800/77A patent/GB1585786A/en not_active Expired
- 1977-07-18 FR FR7721932A patent/FR2365588A1/fr active Granted
-
1978
- 1978-03-07 FR FR7806455A patent/FR2372175A1/fr active Pending
- 1978-03-07 FR FR7806457A patent/FR2372176A1/fr active Pending
- 1978-03-07 FR FR7806456A patent/FR2372174A1/fr active Pending
-
1981
- 1981-06-23 CH CH415381A patent/CH629503A5/de not_active IP Right Cessation
- 1981-06-23 CH CH415281A patent/CH629222A5/de not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CS200517B2 (en) | Process for preparing derivatives of androstan-17-one or androsten-17-one | |
| US4100027A (en) | Process for the preparation of 4-androstene-3,17-dione derivatives | |
| KR960013094B1 (ko) | 에이. 심플렉스(A. simplex)에 의한 스테로이드성 21-에스테르의 1,2-탈수소화 | |
| US4301246A (en) | Process for chenodeoxycholic acid production | |
| US20040220158A1 (en) | 5-Androsten-3beta-ol steroid intermediates and processes for their preparation | |
| CS258482B2 (en) | Method of 4-androstane-3,17-dione and 1,4-androstadiene-3,17-dione production | |
| US4170518A (en) | Microbiological conversion of sterol derivatives to 5-androsten-17-one derivatives and their use | |
| CS200519B2 (cs) | Způsob výroby androstanových derivátů | |
| US4100026A (en) | Process for the preparation of 4-androstene-3,17-dione derivatives | |
| JPS6137280B2 (https=) | ||
| US4097334A (en) | Process for the preparation of androstane-3,17-dione derivatives | |
| US3272847A (en) | Process for preparing equilin and the intermediates produced therein | |
| US3379621A (en) | Microbiological preparation of delta1, 3, 5(10)-3-hydroxy steroids | |
| US3344156A (en) | Process for the preparation of equilin and intermediate obtained therefrom | |
| RU2082762C1 (ru) | Способ получения 17-оксостероидов | |
| JPH0460480B2 (https=) | ||
| JPH02360B2 (https=) | ||
| DK146007B (da) | Analogifremgangsmaade til fremstilling af d-homosteroider | |
| 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 |