DE3306554A1 - Verfahren zur herstellung von 3-((delta)(pfeil hoch)4(pfeil hoch)-3-ketosteroid-17(alpha)-yl)-propionsaeurelactonen - Google Patents
Verfahren zur herstellung von 3-((delta)(pfeil hoch)4(pfeil hoch)-3-ketosteroid-17(alpha)-yl)-propionsaeurelactonenInfo
- Publication number
- DE3306554A1 DE3306554A1 DE19833306554 DE3306554A DE3306554A1 DE 3306554 A1 DE3306554 A1 DE 3306554A1 DE 19833306554 DE19833306554 DE 19833306554 DE 3306554 A DE3306554 A DE 3306554A DE 3306554 A1 DE3306554 A1 DE 3306554A1
- Authority
- DE
- Germany
- Prior art keywords
- alpha
- hydroxy
- arrow
- raney nickel
- steroid
- 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.)
- Withdrawn
Links
- 238000004519 manufacturing process Methods 0.000 title abstract description 5
- -1 propionic acid lactones Chemical class 0.000 claims abstract description 13
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 claims abstract description 5
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 claims abstract description 5
- PCTMTFRHKVHKIS-BMFZQQSSSA-N (1s,3r,4e,6e,8e,10e,12e,14e,16e,18s,19r,20r,21s,25r,27r,30r,31r,33s,35r,37s,38r)-3-[(2r,3s,4s,5s,6r)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-19,25,27,30,31,33,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10 Chemical compound C1C=C2C[C@@H](OS(O)(=O)=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.O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 PCTMTFRHKVHKIS-BMFZQQSSSA-N 0.000 claims abstract 4
- 150000001441 androstanes Chemical class 0.000 claims abstract 2
- 239000007868 Raney catalyst Substances 0.000 claims description 15
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 15
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 10
- 238000005984 hydrogenation reaction Methods 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 abstract description 11
- 150000002596 lactones Chemical class 0.000 abstract description 3
- 235000019260 propionic acid Nutrition 0.000 abstract description 3
- 150000003431 steroids Chemical class 0.000 abstract description 3
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 238000006798 ring closing metathesis reaction Methods 0.000 abstract 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 229940083712 aldosterone antagonist Drugs 0.000 description 2
- 239000002170 aldosterone antagonist Substances 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical class O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 229960000380 propiolactone Drugs 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000006809 Jones oxidation reaction Methods 0.000 description 1
- 239000003810 Jones reagent Substances 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- GHVZOJONCUEWAV-UHFFFAOYSA-N [K].CCO Chemical compound [K].CCO GHVZOJONCUEWAV-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229940117975 chromium trioxide Drugs 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 125000002587 enol group Chemical group 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 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
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 238000009905 homogeneous catalytic hydrogenation reaction Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- RCBVKBFIWMOMHF-UHFFFAOYSA-L hydroxy-(hydroxy(dioxo)chromio)oxy-dioxochromium;pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1.O[Cr](=O)(=O)O[Cr](O)(=O)=O RCBVKBFIWMOMHF-UHFFFAOYSA-L 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- DOKHEARVIDLSFF-UHFFFAOYSA-N prop-1-en-1-ol Chemical compound CC=CO DOKHEARVIDLSFF-UHFFFAOYSA-N 0.000 description 1
- JNLTYWDDGFTRSX-UHFFFAOYSA-N prop-1-ene-1,1-diol Chemical compound CC=C(O)O JNLTYWDDGFTRSX-UHFFFAOYSA-N 0.000 description 1
- DGXZDQFYFRCMJB-UHFFFAOYSA-N prop-1-yne-1,3-diol Chemical compound OCC#CO DGXZDQFYFRCMJB-UHFFFAOYSA-N 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 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 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- FCQRKDSALKMOGU-UHFFFAOYSA-K rhodium(3+);triphenylphosphane;trichloride Chemical compound Cl[Rh](Cl)Cl.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 FCQRKDSALKMOGU-UHFFFAOYSA-K 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 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
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J21/001—Lactones
- C07J21/003—Lactones at position 17
-
- 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19833306554 DE3306554A1 (de) | 1983-02-22 | 1983-02-22 | Verfahren zur herstellung von 3-((delta)(pfeil hoch)4(pfeil hoch)-3-ketosteroid-17(alpha)-yl)-propionsaeurelactonen |
| AT84101780T ATE30728T1 (de) | 1983-02-22 | 1984-02-21 | Verfahren zur herstellung von 3-(delta43ketosteroid-17alpha-yl)-propion-saeurelactonen. |
| DE8484101780T DE3467351D1 (en) | 1983-02-22 | 1984-02-21 | Process for the preparation of 3-(delta-4-3-ketosteroid-17-alpha-yl)propionic acid lactones |
| EP84101780A EP0117507B1 (de) | 1983-02-22 | 1984-02-21 | Verfahren zur Herstellung von 3-(delta4-3ketosteroid-17alpha-yl)-propion-säurelactonen |
| JP59030491A JPS59205398A (ja) | 1983-02-22 | 1984-02-22 | アンドロスタン系の３−（△↑４−３−ケトステロイド−１７α−イル）プロピオン酸ラクトンの製造法 |
| US06/582,644 US4507238A (en) | 1983-02-22 | 1984-02-22 | Process for the preparation of 3-(Δ4 -3-ketosteroid-17α-yl)propionic acid lactones |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19833306554 DE3306554A1 (de) | 1983-02-22 | 1983-02-22 | Verfahren zur herstellung von 3-((delta)(pfeil hoch)4(pfeil hoch)-3-ketosteroid-17(alpha)-yl)-propionsaeurelactonen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3306554A1 true DE3306554A1 (de) | 1984-08-23 |
Family
ID=6191760
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19833306554 Withdrawn DE3306554A1 (de) | 1983-02-22 | 1983-02-22 | Verfahren zur herstellung von 3-((delta)(pfeil hoch)4(pfeil hoch)-3-ketosteroid-17(alpha)-yl)-propionsaeurelactonen |
| DE8484101780T Expired DE3467351D1 (en) | 1983-02-22 | 1984-02-21 | Process for the preparation of 3-(delta-4-3-ketosteroid-17-alpha-yl)propionic acid lactones |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8484101780T Expired DE3467351D1 (en) | 1983-02-22 | 1984-02-21 | Process for the preparation of 3-(delta-4-3-ketosteroid-17-alpha-yl)propionic acid lactones |
Country Status (5)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL115659A (en) * | 1994-10-27 | 2000-06-01 | Akzo Nobel Nv | Steroids with a 17-spiromethylene lactone or lactol group process for their preparation and pharmaceutical compositions containing them |
| ITMI20061802A1 (it) * | 2006-09-22 | 2008-03-23 | Antibioticos Spa | Epossidazione di 17-oxo-15,16-metilen steroidi con ilidi di solfossonio |
| EP2253641A2 (en) | 2007-05-01 | 2010-11-24 | Sicor, Inc. | A process for preparing drospirenone and intermediate thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3455909A (en) * | 1968-05-29 | 1969-07-15 | American Home Prod | 3-desoxy steroidal-1,4-diene lactones and spiroethers |
| US4058522A (en) * | 1973-07-09 | 1977-11-15 | Richter Gedeon Vegyeszeti Gyar Rt. | Steroids effective against heavy-metal poisoning |
| US4057543A (en) * | 1976-07-01 | 1977-11-08 | G. D. Searle & Co. | Process for the preparation of 17β-hydroxy-3-oxo-17α-pregn-4-ene-21-carboxylic acid γ-lactone |
| 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 |
-
1983
- 1983-02-22 DE DE19833306554 patent/DE3306554A1/de not_active Withdrawn
-
1984
- 1984-02-21 DE DE8484101780T patent/DE3467351D1/de not_active Expired
- 1984-02-21 AT AT84101780T patent/ATE30728T1/de not_active IP Right Cessation
- 1984-02-21 EP EP84101780A patent/EP0117507B1/de not_active Expired
- 1984-02-22 JP JP59030491A patent/JPS59205398A/ja active Granted
- 1984-02-22 US US06/582,644 patent/US4507238A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0369359B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1991-10-31 |
| US4507238A (en) | 1985-03-26 |
| EP0117507B1 (de) | 1987-11-11 |
| ATE30728T1 (de) | 1987-11-15 |
| EP0117507A1 (de) | 1984-09-05 |
| DE3467351D1 (en) | 1987-12-17 |
| JPS59205398A (ja) | 1984-11-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1468035C3 (de) | Verfahren zur Herstellung von 19äthylsteroiden und die Verbindung 19äthyl-5alpha-androstan-3beta, 17betadioL | |
| DE3306554A1 (de) | Verfahren zur herstellung von 3-((delta)(pfeil hoch)4(pfeil hoch)-3-ketosteroid-17(alpha)-yl)-propionsaeurelactonen | |
| DE2257132C3 (de) | Verfahren zur Reduktion von 3-Ketosteroiden | |
| CH550156A (de) | Verfahren zur herstellung von 3,6-dihydroxy-(delta)5(10)-steroiden. | |
| DE1183076B (de) | Verfahren zur Herstellung von Steroidlactonen der Androstan- bzw. OEstranreihe | |
| DE1240076B (de) | Verfahren zur Herstellung von 11-Keto-5alpha, 9beta, 10alpha-steroiden der 19-Norandrostan-(oestran-)-bzw. -pregnanreihe | |
| DE1568950C (de) | Verfahren zur Herstellung von Steroideckige Klammer auf 17 alpha, 16 alpha-d eckige Klammer zu -oxyzolinen | |
| DE2206130A1 (de) | Benz eckige Klammer auf e eckige Klammer zu indene und Verfahren zu de ren Herstellung | |
| DE2327448C3 (de) | Verfahren zur Herstellung von 17alpha-(3-Hydroxypropyl)-17beta-hydroxy-3-keto -4-a nd roste n | |
| DE940826C (de) | Verfahren zur Herstellung von substituierten trans-anti-trans-13-Methyl-perhydrophenanthren-1-on-verbindungen | |
| DE963241C (de) | Verfahren zur Herstellung von 5, 16-Pregnadien-3 ª‰-ol-20-on-3-acetat | |
| AT249892B (de) | Verfahren zur Herstellung von 3-Oxo-Δ<4>-6-methyl-steroiden | |
| DE758807C (de) | Verfahren zur Darstellung neuer Oxyketone bzw. deren Ester | |
| DE961536C (de) | Verfahren zur Herstellung von 20-Keto-21-formylsteroiden der Pregnanreihe | |
| DE1096358B (de) | Verfahren zur Herstellung von 3-Amino-oestra-1, 3, 5(10)-trienen | |
| DE1272289B (de) | Verfahren zur Herstellung von 19-Hydroxy-androst-4-en-3, 17-dion | |
| DE1245947B (de) | Vertahren zur Her Stellung von 18 oxygemerten Steroiden der Pregnanreihe | |
| DE2001262A1 (de) | 19-Homosteroide | |
| DD200227A1 (de) | Verfahren zur herstellung von 3 beta-hydroxy-5 beta-h-steroiden | |
| DE1031790B (de) | Verfahren zur Herstellung neuer biologisch aktiver 19-Nor-steroidverbindungen | |
| DE1203258B (de) | Verfahren zur Herstellung von 3-Oxo-A4-6-methyl-steroiden | |
| DE1226576B (de) | Verfahren zur Herstellung von in 17(20)-Stellung ungesaettigten Pregnan-21-alkoholen | |
| DE1300942B (de) | Verfahren zur Herstellung von 19-Hydroxy-ª€ 5-androsten- oder 19-Hydroxy-ª€ 5-pregnenderivaten | |
| DE1163808B (de) | Verfahren zur Herstellung von neuen 20-Hydroxy-18-aldehyden der Pregnanreihe oder funktionellen Derivaten derselben | |
| DE1914898B2 (de) | Verfahren zur herstellung von 3 beta -hydroxy - delta 5 (10) - steroiden |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |