DE2213178A1 - Neue Steroidderivate und Verfahren zu ihrer Herstellung - Google Patents
Neue Steroidderivate und Verfahren zu ihrer HerstellungInfo
- Publication number
- DE2213178A1 DE2213178A1 DE19722213178 DE2213178A DE2213178A1 DE 2213178 A1 DE2213178 A1 DE 2213178A1 DE 19722213178 DE19722213178 DE 19722213178 DE 2213178 A DE2213178 A DE 2213178A DE 2213178 A1 DE2213178 A1 DE 2213178A1
- Authority
- DE
- Germany
- Prior art keywords
- esp
- tert
- dien
- anabolic
- hormonal
- 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.)
- Pending
Links
- 150000003431 steroids Chemical class 0.000 title claims description 7
- 230000001195 anabolic effect Effects 0.000 title description 2
- 230000003054 hormonal effect Effects 0.000 title description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 4
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 8
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000004971 nitroalkyl group Chemical group 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 239000011591 potassium Substances 0.000 claims description 4
- 150000003509 tertiary alcohols Chemical class 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 5
- 239000002585 base Substances 0.000 abstract description 4
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 abstract description 4
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 abstract 2
- BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 abstract 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 230000000269 nucleophilic effect Effects 0.000 description 4
- -1 steroid ketones Chemical class 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000006957 Michael reaction Methods 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OKUWFSWDZQMETE-LEKSSAKUSA-N (8s,9s,10r,13s,14s,17s)-17-acetyl-10,13-dimethyl-8,9,11,12,14,15,16,17-octahydrocyclopenta[a]phenanthren-3-one Chemical compound C1=CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 OKUWFSWDZQMETE-LEKSSAKUSA-N 0.000 description 1
- JSZOAYXJRCEYSX-UHFFFAOYSA-N 1-nitropropane Chemical compound CCC[N+]([O-])=O JSZOAYXJRCEYSX-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- DKVSUQWCZQBWCP-QAGGRKNESA-N androsta-1,4,6-triene-3,17-dione Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3C=CC2=C1 DKVSUQWCZQBWCP-QAGGRKNESA-N 0.000 description 1
- 150000001441 androstanes Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 150000002085 enols Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction 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
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
- 239000012434 nucleophilic reagent Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930000044 secondary metabolite Natural products 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 150000005671 trienes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL14693771A PL76434B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-03-17 | 1971-03-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2213178A1 true DE2213178A1 (de) | 1972-09-21 |
Family
ID=19953792
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722213178 Pending DE2213178A1 (de) | 1971-03-17 | 1972-03-17 | Neue Steroidderivate und Verfahren zu ihrer Herstellung |
Country Status (3)
-
1971
- 1971-03-17 PL PL14693771A patent/PL76434B1/xx unknown
-
1972
- 1972-03-08 CH CH339872A patent/CH579593A5/xx not_active IP Right Cessation
- 1972-03-17 DE DE19722213178 patent/DE2213178A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| PL76434B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-02-28 |
| CH579593A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-09-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2213178A1 (de) | Neue Steroidderivate und Verfahren zu ihrer Herstellung | |
| DE1793704A1 (de) | Verfahren zur Herstellung von in 17-Stellung substituierten 19-Norsteroiden | |
| DE2109555A1 (de) | Neue 15 alpha, 16 alpha-Methylensteroide | |
| DE1296632B (de) | Verfahren zur Herstellung von 3-Oxo-13ª-alkyl-17ª-hydroxy-17ª-aethinylgona-5(10), 9(11)-dienen | |
| DE1643005C3 (de) | 15,16beta-Methylen-testosterone, Verfahren zu ihrer Herstellung sowie diese Steroide enthaltende Mittel | |
| DE1807585C3 (de) | 14,15beta-Epoxycardenolide, Verfahren zu deren Herstellung und diese enthaltende Mittel | |
| DE1543245B2 (de) | 16-Methylen-19-norprogesteronderivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zubereitungen | |
| DE3426771C2 (de) | 13alpha-Methylgonane, deren Herstellung und Verwendung | |
| DE965238C (de) | Verfahren zur Herstellung von in 11(12)-Stellung ungesaettigten Pregnanen | |
| DE961536C (de) | Verfahren zur Herstellung von 20-Keto-21-formylsteroiden der Pregnanreihe | |
| DE2158260C3 (de) | 11-Alkoxysteroide, Verfahren zu deren Herstellung sowie diese enthaltende pharmazeutische Zusammensetzungen | |
| DE1813728C3 (de) | 3-Oxo-A-nor-B-homo-östr-5(10)-ene und ein Verfahren zu deren Herstellung | |
| AT271759B (de) | Verfahren zur Herstellung von neuen 1,2β-Methylensteroiden | |
| DE665512C (de) | Verfahren zur Darstellung neuer, den Sterinkern enthaltender Enolderivate | |
| CH505803A (de) | Verfahren zur Herstellung von 4-3-Ketosteroiden | |
| DE1097986B (de) | Verfahren zur Herstellung von 6ª‡-Methyl-17ª‡-oxyprogesteron sowie von dessen Estern | |
| DE1117575B (de) | Verfahren zur Herstellung von gesaettigten 21-Acyloxy-17ª‡-hydroxy-3-ketosteroiden der Pregnanreihe | |
| DE1094257B (de) | Verfahren zur Herstellung von 2ª‡, 17ª‡-Dimethyl-11ª‰, 17ª‰-dioxyandrostan-3-on | |
| DE1418855A1 (de) | Verfahren zur Herstellung von Steroiden | |
| DE1025413B (de) | Verfahren zur Herstellung von 17-Alkenyl- und 17-Alkinylnortestosteronen | |
| DE1008285B (de) | Verfahren zur Herstellung von 4b-Methyl-1, 2, 3, 4, 4a, 4b, 5, 6, 7, 9, 10, 10a-dodecahydrophen-anthren-4-ol-1, 7-dion | |
| DE1087127B (de) | Verfahren zur Herstellung neuer progestativ wirksamer Ester von 2-Methyl-Steroiden | |
| DE2204366A1 (de) | Steroid-abkoemmlinge | |
| DE1157222B (de) | Verfahren zur Herstellung von 11ª‰,18-Oxido-18ªš-methyl-steroiden | |
| DE1072622B (de) | Verfahren zur Herstellung von 17tt,21-Dioxy-20-kctosteroiden der Pregnanreihe |