CS235333B2 - Method of 7 alpha-acetylthio-15,16-amethylen-3-keto-17 alpha-pregna-1,4-dien-21,17-carbolactones production - Google Patents
Method of 7 alpha-acetylthio-15,16-amethylen-3-keto-17 alpha-pregna-1,4-dien-21,17-carbolactones production Download PDFInfo
- Publication number
- CS235333B2 CS235333B2 CS835482A CS548283A CS235333B2 CS 235333 B2 CS235333 B2 CS 235333B2 CS 835482 A CS835482 A CS 835482A CS 548283 A CS548283 A CS 548283A CS 235333 B2 CS235333 B2 CS 235333B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- alpha
- carbolactones
- keto
- pregna
- acetylthio
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 2
- 230000000694 effects Effects 0.000 abstract description 14
- 239000000126 substance Substances 0.000 abstract description 11
- 238000006356 dehydrogenation reaction Methods 0.000 abstract description 3
- -1 15,16-methylene group Chemical group 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000002906 microbiologic effect Effects 0.000 abstract 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 9
- 229960002256 spironolactone Drugs 0.000 description 9
- 102000005962 receptors Human genes 0.000 description 8
- 108020003175 receptors Proteins 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000000583 progesterone congener Substances 0.000 description 4
- 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 3
- 102000001307 androgen receptors Human genes 0.000 description 3
- 108010080146 androgen receptors Proteins 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000002860 competitive effect Effects 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 230000003152 gestagenic effect Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 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-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
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 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 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229960002478 aldosterone Drugs 0.000 description 2
- 239000002170 aldosterone antagonist Substances 0.000 description 2
- 239000003098 androgen Substances 0.000 description 2
- 230000002280 anti-androgenic effect Effects 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 210000000172 cytosol Anatomy 0.000 description 2
- 230000029142 excretion Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001525 receptor binding assay Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000013558 reference substance Substances 0.000 description 2
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-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
- 241000430521 Alyssum Species 0.000 description 1
- 241000193830 Bacillus <bacterium> Species 0.000 description 1
- 241000193422 Bacillus lentus Species 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 241000193386 Lysinibacillus sphaericus Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000011719 Nomada opaca Species 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- 230000001548 androgenic effect Effects 0.000 description 1
- 229960003473 androstanolone Drugs 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000001864 anti-aldosterone effect Effects 0.000 description 1
- 238000009835 boiling Methods 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
- 229960003654 desoxycortone Drugs 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000002124 endocrine Effects 0.000 description 1
- 208000030172 endocrine system disease Diseases 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 201000000079 gynecomastia Diseases 0.000 description 1
- 201000001881 impotence Diseases 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 229940046892 lead acetate Drugs 0.000 description 1
- 210000003041 ligament Anatomy 0.000 description 1
- 238000011866 long-term treatment Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- HQOJMTATBXYHNR-UHFFFAOYSA-M thallium(I) acetate Chemical compound [Tl+].CC([O-])=O HQOJMTATBXYHNR-UHFFFAOYSA-M 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823227598 DE3227598A1 (de) | 1982-07-22 | 1982-07-22 | 7(alpha)-acylthio-15.16-methylen-3-oxo-17(alpha)-pregna-1.4-dien-21,17-carbolactone, verfahren zu ihrer herstellung und verwendung als arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS235333B2 true CS235333B2 (en) | 1985-05-15 |
Family
ID=6169184
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS835482A CS235333B2 (en) | 1982-07-22 | 1983-07-21 | Method of 7 alpha-acetylthio-15,16-amethylen-3-keto-17 alpha-pregna-1,4-dien-21,17-carbolactones production |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4500522A (en, 2012) |
| EP (1) | EP0099853B1 (en, 2012) |
| JP (1) | JPS5921699A (en, 2012) |
| AT (1) | ATE27606T1 (en, 2012) |
| AU (1) | AU557559B2 (en, 2012) |
| CA (1) | CA1202301A (en, 2012) |
| CS (1) | CS235333B2 (en, 2012) |
| DD (1) | DD210061B3 (en, 2012) |
| DE (2) | DE3227598A1 (en, 2012) |
| DK (1) | DK159457C (en, 2012) |
| ES (1) | ES8407322A1 (en, 2012) |
| FI (1) | FI78112C (en, 2012) |
| GR (1) | GR78904B (en, 2012) |
| HU (1) | HU187114B (en, 2012) |
| IE (1) | IE55667B1 (en, 2012) |
| NO (1) | NO157297C (en, 2012) |
| ZA (1) | ZA835390B (en, 2012) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE51233T1 (de) * | 1983-08-17 | 1990-04-15 | Schering Ag | 7-alpha-substituierte 3-oxo-17alpha-pregn-4-en21.17-carbolactone, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate. |
| DE3402329A1 (de) * | 1984-01-20 | 1985-08-01 | Schering AG, 1000 Berlin und 4709 Bergkamen | 6,6-ethylen-15,16-methylen-3-oxo-17(alpha)-pregn-4-en-21,17-carbolactone, verfahren zu deren herstellung und diese enthaltende pharmazeutische praeparate |
| 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 |
| 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 |
| DE3544661A1 (de) * | 1985-12-13 | 1987-06-19 | Schering Ag | Verfahren zur herstellung von 7(alpha)-acetylthiosteroiden |
| DE3718109A1 (de) * | 1987-05-27 | 1988-12-22 | Schering Ag | Verfahren zur trennung von verfahrensprodukten der mespirenonsynthese |
| JPH01165155U (en, 2012) * | 1988-05-02 | 1989-11-17 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE792624A (fr) * | 1972-05-22 | 1973-06-12 | Merck & Co Inc | Composes inhibiteurs de l'aldosterone et leur obtention |
| DE2237143A1 (de) * | 1972-07-28 | 1974-02-14 | Hoechst Ag | Verfahren zur herstellung von beta(3-keto-7alpha-acetylthio-17beta-hydroxy4-androsten-17alpha-yl)-propionsaeuregamma-lacton und dessen 1-dehydro-derivat |
| US3890304A (en) * | 1973-11-09 | 1975-06-17 | Searle & Co | 7{60 -carbam oyl-17-hydroxy-3-oxo-17{60 -pregn-4-ene-21-carboxylic acid {65 -lactone and related compounds |
| 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 |
| DE2922500A1 (de) * | 1979-05-31 | 1980-12-04 | Schering Ag | 6 beta .7 beta |
-
1982
- 1982-07-22 DE DE19823227598 patent/DE3227598A1/de not_active Withdrawn
-
1983
- 1983-07-07 JP JP58122449A patent/JPS5921699A/ja active Granted
- 1983-07-12 AU AU16756/83A patent/AU557559B2/en not_active Ceased
- 1983-07-19 FI FI832627A patent/FI78112C/fi not_active IP Right Cessation
- 1983-07-19 DD DD83253197A patent/DD210061B3/de not_active IP Right Cessation
- 1983-07-20 AT AT83730074T patent/ATE27606T1/de not_active IP Right Cessation
- 1983-07-20 GR GR71989A patent/GR78904B/el unknown
- 1983-07-20 EP EP83730074A patent/EP0099853B1/en not_active Expired
- 1983-07-20 DE DE8383730074T patent/DE3371909D1/de not_active Expired
- 1983-07-21 HU HU832580A patent/HU187114B/hu unknown
- 1983-07-21 CA CA000432905A patent/CA1202301A/en not_active Expired
- 1983-07-21 CS CS835482A patent/CS235333B2/cs unknown
- 1983-07-21 NO NO832667A patent/NO157297C/no unknown
- 1983-07-21 DK DK335583A patent/DK159457C/da not_active IP Right Cessation
- 1983-07-21 IE IE1708/83A patent/IE55667B1/en not_active IP Right Cessation
- 1983-07-22 ZA ZA835390A patent/ZA835390B/xx unknown
- 1983-07-22 US US06/516,391 patent/US4500522A/en not_active Expired - Fee Related
- 1983-07-22 ES ES524363A patent/ES8407322A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FI78112B (fi) | 1989-02-28 |
| DK159457C (da) | 1991-03-18 |
| DK159457B (da) | 1990-10-15 |
| IE831708L (en) | 1984-01-22 |
| ZA835390B (en) | 1984-03-28 |
| JPS5921699A (ja) | 1984-02-03 |
| HU187114B (en) | 1985-11-28 |
| GR78904B (en, 2012) | 1984-10-02 |
| EP0099853A3 (en) | 1984-04-18 |
| AU557559B2 (en) | 1986-12-24 |
| DE3227598A1 (de) | 1984-01-26 |
| NO157297C (no) | 1988-02-24 |
| DE3371909D1 (en) | 1987-07-09 |
| FI78112C (fi) | 1989-06-12 |
| EP0099853A2 (en) | 1984-02-01 |
| DD210061A5 (de) | 1984-05-30 |
| US4500522A (en) | 1985-02-19 |
| FI832627L (fi) | 1984-01-23 |
| ATE27606T1 (de) | 1987-06-15 |
| AU1675683A (en) | 1984-01-26 |
| DK335583D0 (da) | 1983-07-21 |
| CA1202301A (en) | 1986-03-25 |
| ES524363A0 (es) | 1984-10-01 |
| ES8407322A1 (es) | 1984-10-01 |
| NO832667L (no) | 1984-01-23 |
| NO157297B (no) | 1987-11-16 |
| JPH0372080B2 (en, 2012) | 1991-11-15 |
| FI832627A0 (fi) | 1983-07-19 |
| DK335583A (da) | 1984-01-23 |
| IE55667B1 (en) | 1990-12-19 |
| DD210061B3 (de) | 1988-11-30 |
| EP0099853B1 (en) | 1987-06-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| IE55567B1 (en) | Copper-containing thick-film conductor compositions | |
| PT2038294E (pt) | 18-metil-19-nor-androst-4-en-17,17-espiroéter (18-metil- 19-nor-20-spirox-4-en-3-ona), bem como preparados farmacêuticos contendo estes compostos | |
| EA014325B1 (ru) | 18-метил-9-нор-17-прегн-4-ен-21,17-карболактоны, а также лекарственные препараты, которые их содержат | |
| CS235333B2 (en) | Method of 7 alpha-acetylthio-15,16-amethylen-3-keto-17 alpha-pregna-1,4-dien-21,17-carbolactones production | |
| KR20100028554A (ko) | 17β-시아노-19-노르-안드로스트-4-엔 유도체, 그의 용도, 및 상기 유도체를 함유하는 의약 | |
| US8987239B2 (en) | 19-nor-steroid derivatives with a 15α,16α-methylene group and a saturated 17,17-spirolactone ring, use thereof, and medicaments containing said derivatives | |
| EP0099854B1 (en) | 17-alpha-pregn-4-ene-3-oxo-21-carboxylic acid esters, process for the preparation thereof, and use thereof as medicinal agents | |
| US8937058B2 (en) | 17-hydroxy-19-nor-21-carboxylic acid-steroid γ-lactone derivative, use thereof, and medicament containing the derivative | |
| AU2008342915A1 (en) | 15,16-methylene-17-(1'-propenyl)-17,3'-oxidoestra-4-en-3-one derivative, use thereof, and medicament containing said derivative | |
| EP0108033B1 (de) | 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 | |
| US20110015162A1 (en) | 15,16-Methylene-17-hydroxy-19-nor-21-carboxylic acid-steroid Y-lactone derivative, use thereof and medicinal products containing the derivative | |
| US9034856B2 (en) | 17-(1′propenyl)-17-3′-oxidoestra-4-en-3-one derivative, use thereof, and medicament containing said derivative | |
| EP0255464B1 (de) | 2,2;6,6-Diethylen-3-oxo-17alpha-pregn-4-en-21, 17-carbolactone, Verfahren zu deren Herstellung und diese enthaltende pharm. Präparate | |
| US3441647A (en) | 1,2alpha;16,17alpha-bismethylene-delta**4,6-pregnadienes | |
| JPS595200A (ja) | ６β，７β−メチレン−１７α−プレグネ−４−エン−２１，１７−カルボラクトン、その製造法及びこれを含有しアルドステロン拮抗作用を有する薬剤 | |
| 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 | |
| SI8611201A8 (sl) | Postopek za pridobivanje substituiranih androsta -1,4-dien-3,17-dionov | |
| DE3140823A1 (de) | 6-chlor-6.7;15ss.16ss-dimethylen-3-keto-steroid- 21.17-carbolactone, verfahren zu ihrer herstellung und verwendung als arzneimittel |