JPS5989700A - 新規７α−アシルチオ−１α，２α−メチレン−３−オキソ−１７α−プレグネ−４−エン−２１，１７−カルボラクトン、その製法及びこれを含有する抗アルドステロン作用剤 - Google Patents
新規７α−アシルチオ−１α，２α−メチレン−３−オキソ−１７α−プレグネ−４−エン−２１，１７−カルボラクトン、その製法及びこれを含有する抗アルドステロン作用剤Info
- Publication number
- JPS5989700A JPS5989700A JP58193590A JP19359083A JPS5989700A JP S5989700 A JPS5989700 A JP S5989700A JP 58193590 A JP58193590 A JP 58193590A JP 19359083 A JP19359083 A JP 19359083A JP S5989700 A JPS5989700 A JP S5989700A
- Authority
- JP
- Japan
- Prior art keywords
- oxo
- alpha
- ene
- methylene
- acylthio
- Prior art date
- 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
Links
- 239000002170 aldosterone antagonist Substances 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 5
- 150000001875 compounds Chemical class 0.000 claims description 14
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 150000002596 lactones Chemical class 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 239000003586 protic polar solvent Substances 0.000 claims description 2
- 230000000694 effects Effects 0.000 abstract description 13
- 230000001864 anti-aldosterone effect Effects 0.000 abstract 1
- 102000005962 receptors Human genes 0.000 description 11
- 108020003175 receptors Proteins 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 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 9
- 229960002256 spironolactone Drugs 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 239000000583 progesterone congener Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 230000002280 anti-androgenic effect Effects 0.000 description 3
- 230000002124 endocrine Effects 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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
- 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 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 229960002478 aldosterone Drugs 0.000 description 2
- 239000003098 androgen Substances 0.000 description 2
- 230000002860 competitive effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YRYSAWZMIRQUBO-UHFFFAOYSA-N trimethylsulfoxonium Chemical compound C[S+](C)(C)=O YRYSAWZMIRQUBO-UHFFFAOYSA-N 0.000 description 2
- OVBICQMTCPFEBS-SATRDZAXSA-N (2s)-1-[(2s)-2-[[(2s)-2-[[(2r)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-[[(2r)-2-[[(2r)-2-acetamido-3-naphthalen-2-ylpropanoyl]amino]-3-(4-chlorophenyl)propanoyl]amino]-3-pyridin-3-ylpropanoyl]amino]-3-hydroxypropanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-6-[bi Chemical compound CC(O)=O.CC(O)=O.C([C@@H](C(=O)N[C@H](CCCCN=C(NCC)NCC)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN=C(NCC)NCC)C(=O)N1[C@@H](CCC1)C(=O)N[C@H](C)C(N)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](CC=1C=NC=CC=1)NC(=O)[C@@H](CC=1C=CC(Cl)=CC=1)NC(=O)[C@@H](CC=1C=C2C=CC=CC2=CC=1)NC(C)=O)C1=CC=C(O)C=C1 OVBICQMTCPFEBS-SATRDZAXSA-N 0.000 description 1
- ZESRJSPZRDMNHY-YFWFAHHUSA-N 11-deoxycorticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 ZESRJSPZRDMNHY-YFWFAHHUSA-N 0.000 description 1
- 201000000736 Amenorrhea Diseases 0.000 description 1
- 206010001928 Amenorrhoea Diseases 0.000 description 1
- 208000016998 Conn syndrome Diseases 0.000 description 1
- 208000017701 Endocrine disease Diseases 0.000 description 1
- 241000195522 Fucales Species 0.000 description 1
- 206010020772 Hypertension 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
- 241001465754 Metazoa Species 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000084978 Rena Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 231100000540 amenorrhea Toxicity 0.000 description 1
- 102000001307 androgen receptors Human genes 0.000 description 1
- 108010080146 androgen receptors Proteins 0.000 description 1
- 229940030486 androgens Drugs 0.000 description 1
- 229960003473 androstanolone Drugs 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 1
- 210000000172 cytosol Anatomy 0.000 description 1
- ZESRJSPZRDMNHY-UHFFFAOYSA-N de-oxy corticosterone Natural products O=C1CCC2(C)C3CCC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 ZESRJSPZRDMNHY-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229960003654 desoxycortone Drugs 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 108700032141 ganirelix Proteins 0.000 description 1
- 230000003152 gestagenic effect Effects 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011866 long-term treatment Methods 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 208000013846 primary aldosteronism Diseases 0.000 description 1
- 201000009395 primary hyperaldosteronism Diseases 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001525 receptor binding assay Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- URGUBECARCAPRI-UHFFFAOYSA-N tirandamycin A Natural products O1C(C2(OC2C2=O)C)(C)OC2C(C)C1C(C)C=C(C)C=CC(O)=C1C(=O)CNC1=O URGUBECARCAPRI-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 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
-
- 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
-
- 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
- A61P5/38—Drugs for disorders of the endocrine system of the suprarenal hormones
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Endocrinology (AREA)
- Diabetes (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Peptides Or Proteins (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823240510 DE3240510A1 (de) | 1982-10-29 | 1982-10-29 | Neue 7(alpha)-acylthio-1(alpha),2(alpha)-methylen-3-oxo-17(alpha)-pregn-4-en-21,17-carbolactone, deren herstellung und diese enthaltende arzneimittel |
| DE3240510.3 | 1982-10-29 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5989700A true JPS5989700A (ja) | 1984-05-23 |
| JPH0436160B2 JPH0436160B2 (en, 2012) | 1992-06-15 |
Family
ID=6177150
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58193590A Granted JPS5989700A (ja) | 1982-10-29 | 1983-10-18 | 新規７α−アシルチオ−１α，２α−メチレン−３−オキソ−１７α−プレグネ−４−エン−２１，１７−カルボラクトン、その製法及びこれを含有する抗アルドステロン作用剤 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4511565A (en, 2012) |
| EP (1) | EP0108033B1 (en, 2012) |
| JP (1) | JPS5989700A (en, 2012) |
| AT (1) | ATE31192T1 (en, 2012) |
| AU (1) | AU556675B2 (en, 2012) |
| CA (1) | CA1203233A (en, 2012) |
| DE (2) | DE3240510A1 (en, 2012) |
| DK (1) | DK496283A (en, 2012) |
| ES (1) | ES8405813A1 (en, 2012) |
| IE (1) | IE56178B1 (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6248694A (ja) * | 1985-08-28 | 1987-03-03 | Shionogi & Co Ltd | 抗アルドステロン活性ステロイド誘導体 |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3427090A1 (de) * | 1984-07-19 | 1986-01-23 | Schering AG, 1000 Berlin und 4709 Bergkamen | 7(alpha)-thiosubstituierte 19-hydroxy-15(beta),16(beta)-methylen-3-oxo-17(alpha)-pregn-4-en-21,17-carbolactone, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| DE3506100A1 (de) * | 1985-02-18 | 1986-08-21 | Schering AG, 1000 Berlin und 4709 Bergkamen | 1(alpha).7(alpha)-dithiosubstituierte spirolactone, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| US20130123523A1 (en) * | 2011-11-10 | 2013-05-16 | Klaus Nickisch | Methods for the preparation of etonogestrel and desogestrel |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3013012A (en) * | 1960-12-22 | 1961-12-12 | Searle & Co | Alkanoylthio-17alpha-carboxyethyl-17beta-hydroxyandrosten-3-one lactones |
| US3753979A (en) * | 1971-12-06 | 1973-08-21 | Merck & Co Inc | Substituted 1,2alpha-methylene-6,7alpha-halomethylene-20-spirox-4-en-3-ones or 3-ols and acyl esters thereof |
| DE2652761C2 (de) * | 1976-11-16 | 1985-11-21 | Schering AG, 1000 Berlin und 4709 Bergkamen | 15,16-Methylen-Spirolactone, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel |
| JPS5842879B2 (ja) * | 1979-05-14 | 1983-09-22 | 三菱化学株式会社 | ステロイドカルボン酸塩の製造法 |
| DE2922500A1 (de) * | 1979-05-31 | 1980-12-04 | Schering Ag | 6 beta .7 beta |
-
1982
- 1982-10-29 DE DE19823240510 patent/DE3240510A1/de not_active Withdrawn
-
1983
- 1983-10-14 DE DE8383730098T patent/DE3374784D1/de not_active Expired
- 1983-10-14 AT AT83730098T patent/ATE31192T1/de not_active IP Right Cessation
- 1983-10-14 EP EP83730098A patent/EP0108033B1/de not_active Expired
- 1983-10-18 JP JP58193590A patent/JPS5989700A/ja active Granted
- 1983-10-28 AU AU20697/83A patent/AU556675B2/en not_active Ceased
- 1983-10-28 ES ES526898A patent/ES8405813A1/es not_active Expired
- 1983-10-28 IE IE2531/83A patent/IE56178B1/en not_active IP Right Cessation
- 1983-10-28 CA CA000440008A patent/CA1203233A/en not_active Expired
- 1983-10-28 DK DK496283A patent/DK496283A/da not_active Application Discontinuation
- 1983-10-28 US US06/546,352 patent/US4511565A/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6248694A (ja) * | 1985-08-28 | 1987-03-03 | Shionogi & Co Ltd | 抗アルドステロン活性ステロイド誘導体 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3374784D1 (en) | 1988-01-14 |
| EP0108033B1 (de) | 1987-12-02 |
| JPH0436160B2 (en, 2012) | 1992-06-15 |
| US4511565A (en) | 1985-04-16 |
| DK496283A (da) | 1984-04-30 |
| IE56178B1 (en) | 1991-05-08 |
| EP0108033A1 (de) | 1984-05-09 |
| CA1203233A (en) | 1986-04-15 |
| ES526898A0 (es) | 1984-07-01 |
| ES8405813A1 (es) | 1984-07-01 |
| ATE31192T1 (de) | 1987-12-15 |
| AU556675B2 (en) | 1986-11-13 |
| AU2069783A (en) | 1984-05-03 |
| DE3240510A1 (de) | 1984-05-03 |
| DK496283D0 (da) | 1983-10-28 |
| IE832531L (en) | 1984-04-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5626616B2 (ja) | ドロスピレノンの調製方法 | |
| AU2007263944B2 (en) | 18-methyl-19-nor-androst-4-en-17,17-spiroether (18-methyl-19-nor-20- spirox-4-en-3-one) and pharmaceutical preparations containing the same | |
| DE3708942A1 (de) | 19,11ss-ueberbrueckte steroide, deren herstellung und diese enthaltende pharmazeutische praeparate | |
| WO1983003099A1 (en) | 3-keto-delta 4,9-19-norsteroids | |
| JP2001507365A (ja) | ステロイドスルファメート、その製造方法、及びその使用 | |
| DE69523622T2 (de) | Diastereomerenreine 3-oxo und 3-thioxo-4-aza-androstanderivate und ihre verwendung als antiandrogene | |
| Djerassi et al. | Steroids. XLVIII. 1 19-Norprogesterone, a Potent Progestational Hormone | |
| JPS5989700A (ja) | 新規７α−アシルチオ−１α，２α−メチレン−３−オキソ−１７α−プレグネ−４−エン−２１，１７−カルボラクトン、その製法及びこれを含有する抗アルドステロン作用剤 | |
| DE3130644A1 (de) | Neue androstan-derivate, verfahren zu ihrer herstellung und pharmazeutische praeparate, die diese verbindungen enthalten | |
| JPS6176499A (ja) | 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 | |
| EP0156284A2 (de) | 17-Substituierte Estradiene | |
| NO157297B (no) | Analogifremgangsmaate ved fremstilling av terapeutisk aktive 7alfa-acylthio-15,16-methylen-3-oxo-17alfa-pregna-1,4-dien-21,17-carbolactoner. | |
| ITRM950303A1 (it) | Nuovi seco-d steroidi sul sistema cardiovascolare, processi per la loro preparazione e composizioni farmaceutiche che li contengono. | |
| JPH0411558B2 (en, 2012) | ||
| JPS581000A (ja) | ４α，５α−エポキシ−３，２０−ジオキソプレグナン−２α，１６α−ジカルボニトリル，その製造法およびそれを含む製薬学的組成物 | |
| Shapiro et al. | Synthesis and progestational activity of some 1, 2. alpha.-cyclomethylene-16-methylene progesterone derivatives | |
| Miyano | Regioselective synthesis using the deuterium isotope effect | |
| US4868166A (en) | 2,2:6,6-diethylen-3-oxo-17alpha-pregn-4-ene-21,17alpha-carbolactones, process for their production & pharmaceutical preparations containing them | |
| HU193694B (en) | Process for preparing 7 alpha-substituted-3-oxo-17 alpha-pregn-4-ene-21,17-carbolactone derivatives and pharmaceutics comprising the same as active substance | |
| OTTO et al. | Investigations on Steroids. XXXIV. 8, 19-Epoxyprogesterone and 8, 19-Epoxycortexone1, 2 | |
| JPH0378400B2 (en, 2012) | ||
| JPS5970700A (ja) | ７α−アルキル−１７α−プレグン−４−エン−２１，１７−カルボラクトン及び−２１−カルボン酸塩、その製法並びに該化合物を含有する抗アルドステロン作用を有する製薬的製剤 | |
| DE3427090A1 (de) | 7(alpha)-thiosubstituierte 19-hydroxy-15(beta),16(beta)-methylen-3-oxo-17(alpha)-pregn-4-en-21,17-carbolactone, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel | |
| TANASE et al. | Studies on Cardiac Ingredients of Plants. XI. Synthesis of New Bufotoxin Homologues Utilizing Scillarenin (the Genuine Aglycone of Proscillaridin), and Their Biological Activities | |
| Bowers et al. | Synthesis of halogenated steroid hormones—II |