JPS5921698A - １７α−プレグネ−４−エン−３−オキソ−２１−カルボン酸エステル、その製法およびこれを含有する抗アンドロゲン作用を有する医薬 - Google Patents

１７α−プレグネ−４−エン−３−オキソ−２１−カルボン酸エステル、その製法およびこれを含有する抗アンドロゲン作用を有する医薬

Info

Publication number: JPS5921698A
Authority: JP; Japan
Prior art keywords: oxo; carboxylic acid; ester; ene; hydroxy
Prior art date: 1982-07-22
Legal status (The legal status 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 status listed.): Granted

Application number

JP58122450A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0373560B2 (2

Inventor

デイ−タ−・ビトラ−

ヘンリ−・ラウレント

クラウス・ニキシユ

ルドルフ・ヴイ−ヒエルト

ホルゲ・カザルス−ステンツエル

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer Pharma AG

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.)

1982-07-22

Filing date

1983-07-07

Publication date

1984-02-03

1983-07-07 Application filed by Schering AG filed Critical Schering AG

1984-02-03 Publication of JPS5921698A publication Critical patent/JPS5921698A/ja

1991-11-22 Publication of JPH0373560B2 publication Critical patent/JPH0373560B2/ja

Status Granted legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims description 6
239000003814 drug Substances 0.000 title claims description 5
230000002280 anti-androgenic effect Effects 0.000 title description 2
150000002148 esters Chemical class 0.000 claims description 25
150000001875 compounds Chemical class 0.000 claims description 21
239000002253 acid Substances 0.000 claims description 18
-1 monomethyl ester Chemical class 0.000 claims description 14
125000003342 alkenyl group Chemical group 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 5
230000001864 anti-aldosterone effect Effects 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
229940079593 drug Drugs 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
230000007935 neutral effect Effects 0.000 claims description 3
239000002904 solvent Substances 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
JWHOQZUREKYPBY-UHFFFAOYSA-N rubonic acid Natural products CC1(C)CCC2(CCC3(C)C(=CCC4C5(C)CCC(=O)C(C)(C)C5CC(=O)C34C)C2C1)C(=O)O JWHOQZUREKYPBY-UHFFFAOYSA-N 0.000 claims description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 90
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 39
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 36
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 20
238000002844 melting Methods 0.000 description 15
230000008018 melting Effects 0.000 description 15
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 15
235000012239 silicon dioxide Nutrition 0.000 description 15
239000000243 solution Substances 0.000 description 15
230000000694 effects Effects 0.000 description 13
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 12
239000011591 potassium Substances 0.000 description 12
229910052700 potassium Inorganic materials 0.000 description 12
238000003756 stirring Methods 0.000 description 12
238000010626 work up procedure Methods 0.000 description 12
238000000034 method Methods 0.000 description 11
239000003921 oil Substances 0.000 description 11
235000019198 oils Nutrition 0.000 description 11
239000000126 substance Substances 0.000 description 11
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 10
229960001760 dimethyl sulfoxide Drugs 0.000 description 10
239000000203 mixture Substances 0.000 description 10
238000012360 testing method Methods 0.000 description 9
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 8
238000004587 chromatography analysis Methods 0.000 description 8
102000005962 receptors Human genes 0.000 description 8
108020003175 receptors Proteins 0.000 description 8
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 7
238000011282 treatment Methods 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
239000012043 crude product Substances 0.000 description 6
239000000047 product Substances 0.000 description 6
UKUVVAMSXXBMRX-UHFFFAOYSA-N 2,4,5-trithia-1,3-diarsabicyclo[1.1.1]pentane Chemical compound S1[As]2S[As]1S2 UKUVVAMSXXBMRX-UHFFFAOYSA-N 0.000 description 5
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 5
239000003208 petroleum Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
MOQOOKGPCBQMCY-UHFFFAOYSA-N acetic acid;hexane Chemical compound CC(O)=O.CCCCCC MOQOOKGPCBQMCY-UHFFFAOYSA-N 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 3
239000010931 gold Substances 0.000 description 3
229910052737 gold Inorganic materials 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
PQSUYGKTWSAVDQ-ZVIOFETBSA-N Aldosterone Chemical compound C([C@@]1([C@@H](C(=O)CO)CC[C@H]1[C@@H]1CC2)C=O)[C@H](O)[C@@H]1[C@]1(C)C2=CC(=O)CC1 PQSUYGKTWSAVDQ-ZVIOFETBSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
238000000576 coating method Methods 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
230000029142 excretion Effects 0.000 description 2
239000003925 fat Substances 0.000 description 2
239000005457 ice water Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
239000010452 phosphate Substances 0.000 description 2
238000012805 post-processing Methods 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
150000003431 steroids Chemical class 0.000 description 2
150000003462 sulfoxides Chemical class 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
HLVFKOKELQSXIQ-UHFFFAOYSA-N 1-bromo-2-methylpropane Chemical compound CC(C)CBr HLVFKOKELQSXIQ-UHFFFAOYSA-N 0.000 description 1
MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 1
NVKAWKQGWWIWPM-ABEVXSGRSA-N 17-β-hydroxy-5-α-Androstan-3-one Chemical compound C1C(=O)CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CC[C@H]21 NVKAWKQGWWIWPM-ABEVXSGRSA-N 0.000 description 1
YZBOVSFWWNVKRJ-UHFFFAOYSA-M 2-butoxycarbonylbenzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1C([O-])=O YZBOVSFWWNVKRJ-UHFFFAOYSA-M 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
OHXAOPZTJOUYKM-UHFFFAOYSA-N 3-Chloro-2-methylpropene Chemical compound CC(=C)CCl OHXAOPZTJOUYKM-UHFFFAOYSA-N 0.000 description 1
JJPWJEGNCRGGGA-UHFFFAOYSA-N 4-[[2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]acetyl]amino]benzoic acid Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)NC1=CC=C(C(=O)O)C=C1 JJPWJEGNCRGGGA-UHFFFAOYSA-N 0.000 description 1
PQSUYGKTWSAVDQ-UHFFFAOYSA-N Aldosterone Natural products C1CC2C3CCC(C(=O)CO)C3(C=O)CC(O)C2C2(C)C1=CC(=O)CC2 PQSUYGKTWSAVDQ-UHFFFAOYSA-N 0.000 description 1
201000000736 Amenorrhea Diseases 0.000 description 1
206010001928 Amenorrhoea Diseases 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
101150110104 CORO6 gene Proteins 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
239000005973 Carvone Substances 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
206010020852 Hypertonia Diseases 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
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
206010027339 Menstruation irregular Diseases 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
241001475023 Neope Species 0.000 description 1
206010030113 Oedema Diseases 0.000 description 1
241000233855 Orchidaceae Species 0.000 description 1
206010041349 Somnolence Diseases 0.000 description 1
244000062793 Sorghum vulgare Species 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
229960002478 aldosterone Drugs 0.000 description 1
239000002170 aldosterone antagonist Substances 0.000 description 1
231100000540 amenorrhea Toxicity 0.000 description 1
229960003473 androstanolone Drugs 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
239000013040 bath agent Substances 0.000 description 1
OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
210000000481 breast Anatomy 0.000 description 1
239000000872 buffer Substances 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
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Substances OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
239000013065 commercial product Substances 0.000 description 1
230000002860 competitive effect Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
210000000172 cytosol Anatomy 0.000 description 1
238000011161 development Methods 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
TXEDBPFZRNBYGP-UHFFFAOYSA-N dimethyl hydrogen phosphate;methyl dihydrogen phosphate Chemical compound COP(O)(O)=O.COP(O)(=O)OC TXEDBPFZRNBYGP-UHFFFAOYSA-N 0.000 description 1
239000001177 diphosphate Substances 0.000 description 1
235000011180 diphosphates Nutrition 0.000 description 1
KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical compound [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 1
239000008298 dragée Substances 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
230000002124 endocrine Effects 0.000 description 1
150000002168 ethanoic acid esters Chemical class 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
238000002474 experimental method Methods 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
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
230000033444 hydroxylation Effects 0.000 description 1
238000005805 hydroxylation reaction Methods 0.000 description 1
229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
239000007943 implant Substances 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
229940102223 injectable solution Drugs 0.000 description 1
230000035987 intoxication Effects 0.000 description 1
231100000566 intoxication Toxicity 0.000 description 1
239000011630 iodine Chemical group 0.000 description 1
150000002497 iodine compounds Chemical class 0.000 description 1
238000005304 joining Methods 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229940057995 liquid paraffin Drugs 0.000 description 1
238000011068 loading method Methods 0.000 description 1
238000011866 long-term treatment Methods 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000005394 methallyl group Chemical group 0.000 description 1
PRFDQHCVOVMMJC-UHFFFAOYSA-N methyl phosphono hydrogen phosphate Chemical compound COP(O)(=O)OP(O)(O)=O PRFDQHCVOVMMJC-UHFFFAOYSA-N 0.000 description 1
235000019713 millet Nutrition 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000002304 perfume Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
229940127557 pharmaceutical product Drugs 0.000 description 1
239000000049 pigment Substances 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
239000002994 raw material Substances 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000001525 receptor binding assay Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
LXMSZDCAJNLERA-ZHYRCANASA-N spironolactone Chemical compound C([C@@H]1[C@]2(C)CC[C@@H]3[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)SC(=O)C)C[C@@]21CCC(=O)O1 LXMSZDCAJNLERA-ZHYRCANASA-N 0.000 description 1
229960002256 spironolactone Drugs 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000004575 stone Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
MYVIATVLJGTBFV-UHFFFAOYSA-M thiamine(1+) chloride Chemical compound [Cl-].CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N MYVIATVLJGTBFV-UHFFFAOYSA-M 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- 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
- C07J53/008—3 membered carbocyclic rings in position 15/16
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J51/00—Normal steroids with unmodified cyclopenta(a)hydrophenanthrene skeleton not provided for in groups C07J1/00 - C07J43/00
- 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
- C07J53/007—3 membered carbocyclic rings in position 6-7

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Steroid Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP58122450A 1982-07-22 1983-07-07 １７α−プレグネ−４−エン−３−オキソ−２１−カルボン酸エステル、その製法およびこれを含有する抗アンドロゲン作用を有する医薬 Granted JPS5921698A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE3227597		1982-07-22
DE3227597.8		1982-07-22

Publications (2)

Publication Number	Publication Date
JPS5921698A true JPS5921698A (ja)	1984-02-03
JPH0373560B2 JPH0373560B2 (2)	1991-11-22

Family

ID=6169183

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP58122450A Granted JPS5921698A (ja)	1982-07-22	1983-07-07	１７α−プレグネ−４−エン−３−オキソ−２１−カルボン酸エステル、その製法およびこれを含有する抗アンドロゲン作用を有する医薬

Country Status (6)

Country	Link
US (1)	US4542128A (2)
EP (1)	EP0099854B1 (2)
JP (1)	JPS5921698A (2)
AT (1)	ATE27459T1 (2)
DE (1)	DE3371787D1 (2)
IE (1)	IE55666B1 (2)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH0447849U (2) *	1990-08-24	1992-04-23

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3326013A1 (de) *	1983-07-15	1985-01-24	Schering AG, 1000 Berlin und 4709 Bergkamen	15,16-methylen-17(alpha)-pregna-4,6-dien-21-carbonsaeuresalze, diese enthaltende pharmazeutische praeparate sowie verfahren zu deren herstellung
EP0134529B1 (de) *	1983-08-17	1990-03-21	Schering Aktiengesellschaft	7-alpha-Substituierte 3-Oxo-17alpha-pregn-4-en-21.17-carbolactone, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate
DE3824247A1 (de) *	1988-07-13	1990-01-18	Schering Ag	Neue androstan-derivate
US8334375B2 (en) *	2009-04-10	2012-12-18	Evestra, Inc.	Methods for the preparation of drospirenone

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2705712A (en) *	1953-09-21	1955-04-05	Searle & Co	Cyclopentanophenanthrene lactones
CH606089A5 (en) *	1972-12-29	1978-10-13	Merck & Co Inc	3'-(3-oxo-17-beta-hydroxy-6,7-methylene-androst-(or
US3919199A (en) *	1974-06-13	1975-11-11	Searle & Co	6-Cyanomethylene-3{62 ,5{60 -17-trihydroxy-17{60 -pregnane-21-carboxylic acid-{65 -lactone and intermediates
US4069219A (en) *	1976-12-27	1978-01-17	G. D. Searle & Co.	7ξ-(Alkoxycarbonyl)-6ξ-alkyl/halo-17-hydroxy-3-oxo-17α-pregn-4-ene-21-carboxylic acid γ-lactones and corresponding 21-carboxylic acids, their salts, and esters
ES469510A1 (es) *	1977-05-16	1978-12-01	Schering Ag	Procedimiento para la preparacion de 17beta hidroxi-4-an- drosten-3-onas.
DE2922500A1 (de) *	1979-05-31	1980-12-04	Schering Ag	6 beta .7 beta

1983
- 1983-07-07 JP JP58122450A patent/JPS5921698A/ja active Granted
- 1983-07-20 EP EP83730075A patent/EP0099854B1/en not_active Expired
- 1983-07-20 DE DE8383730075T patent/DE3371787D1/de not_active Expired
- 1983-07-20 AT AT83730075T patent/ATE27459T1/de not_active IP Right Cessation
- 1983-07-21 IE IE1707/83A patent/IE55666B1/en not_active IP Right Cessation
- 1983-07-22 US US06/516,398 patent/US4542128A/en not_active Expired - Fee Related

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH0447849U (2) *	1990-08-24	1992-04-23

Also Published As

Publication number	Publication date
IE831707L (en)	1984-01-22
EP0099854A2 (en)	1984-02-01
US4542128A (en)	1985-09-17
DE3371787D1 (en)	1987-07-02
EP0099854B1 (en)	1987-05-27
EP0099854A3 (en)	1984-04-18
ATE27459T1 (de)	1987-06-15
IE55666B1 (en)	1990-12-19
JPH0373560B2 (2)	1991-11-22

Publication	Publication Date	Title
JP6130087B1 (ja)	2017-05-17	１７−ヒドロキシ−１７−ペンタフルオロエチル−エストラ−４，９（１０）−ジエン−１１−アリール誘導体、その製造方法、その誘導体を利用した諸疾患の治療
CN101652142B (zh)	2013-01-02	盐皮质激素受体拮抗剂
JPS59231100A (ja)	1984-12-25	２０−スピロオキサン及びｅ環の開環されている類縁体、これらの製造方法及び医薬製剤
JPH02243698A (ja)	1990-09-27	性ステロイド活性を抑制するために用いるエストロゲン核誘導体の薬学組成物
JPS62142198A (ja)	1987-06-25	新規中間体
JPS5921698A (ja)	1984-02-03	１７α−プレグネ−４−エン−３−オキソ−２１−カルボン酸エステル、その製法およびこれを含有する抗アンドロゲン作用を有する医薬
NO177961B (no)	1995-09-18	Analogifremgangsmåte for fremstilling av tetrazol-substituerte benzonitriler
JPS59139400A (ja)	1984-08-10	抗アルドステロン活性ステロイド誘導体
JPS6176499A (ja)	1986-04-18	二重結合又は三重結合を含む基で１０位置が置換された新規なステロイド、それらの製造法及び薬剤
PT1226155E (pt)	2007-07-26	18-nor-esteróides como estrogénios selectivamente activos
EP0099853B1 (en)	1987-06-03	7-alpha-acylthio-15,16-methylene-3-oxo-17-alpha-pregna-1,4-diene-21,17-carbolactones, their preparation and use as medicinal agents
JPH02188599A (ja)	1990-07-24	３―ケト―デルタ―４，９―１９―ノルステロイドから誘導される新物質及びそれらよりなる薬剤
CN112851741B (zh)	2022-10-25	一种取代的甾体类化合物及其应用
EP2999469A1 (de)	2016-03-30	Pharmazeutische zusammensetzung und deren verwendung sowie anwendungsregime dieser pharmazeutischen zusammensetzung zur bedarfsweisen ( on-demand") kontrazeption
EP1090027B1 (fr)	2003-04-16	Nouveaux 19-nor steroides 17-halogenes, procede et intermediaires de preparation, application comme medicaments et compositions pharmaceutiques les renfermant
JPH06329697A (ja)	1994-11-29	骨疾患治療剤
JPS61502186A (ja)	1986-10-02	１７αβ−ヒドロキシ−７α−メチル−Ｄ−ホモ−１９−ノルアンドロスト−４，１６−ジエン−３−オンおよびその１７−エステル、ならびにその製法および使用
JPS5862161A (ja)	1983-04-13	アミノメチル−１ｈ−インド−ル−４−メタノ−ルの新誘導体及びそれらの塩、これらの製造方法及び中間体、これらの薬剤としての使用並びにこれを含有する組成物
EP0096358B1 (en)	1986-09-17	6-beta,7-beta-methylene-17-alpha-pregn-4-ene-21,17-carbolactones, their preparation and use as medicinal agents
MC1318A1 (fr)	1981-03-10	Dea-steroides
DE102005057421A1 (de)	2007-05-31	Heteroaromatische Sulfonamid-Prodrugs
JPS63280095A (ja)	1988-11-17	１５，１９−ジ置換４−アンドロステン−３，１７−ジオン、その製造法、ならびに該化合物を含有する、エストロゲン生合成抑制作用および妊娠調整作用を有する医薬品
WO2014187793A1 (de)	2014-11-27	Verwendung einer pharmazeutischen zusammensetzung zur notfallkontrazeption

JPS5921698A - １７α−プレグネ−４−エン−３−オキソ−２１−カルボン酸エステル、その製法およびこれを含有する抗アンドロゲン作用を有する医薬 - Google Patents

Info

Links

Classifications

Landscapes

Applications Claiming Priority (2)

Publications (2)

Family

ID=6169183

Family Applications (1)

Country Status (6)

Cited By (1)

Families Citing this family (4)

Family Cites Families (6)

Cited By (1)

Also Published As

Similar Documents