DE864255C - Verfahren zur Herstellung von A4,5 ungesaettigten 3-Ketoverbindungen der Androstanreihe - Google Patents
Verfahren zur Herstellung von A4,5 ungesaettigten 3-Ketoverbindungen der AndrostanreiheInfo
- Publication number
- DE864255C DE864255C DESCH3573D DESC003573D DE864255C DE 864255 C DE864255 C DE 864255C DE SCH3573 D DESCH3573 D DE SCH3573D DE SC003573 D DESC003573 D DE SC003573D DE 864255 C DE864255 C DE 864255C
- Authority
- DE
- Germany
- Prior art keywords
- unsaturated
- series
- androstane
- production
- keto compounds
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 7
- 150000001441 androstanes Chemical class 0.000 title claims description 5
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 5
- 239000012433 hydrogen halide Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- 238000003776 cleavage reaction Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 230000007017 scission Effects 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 235000005985 organic acids Nutrition 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000000126 substance Substances 0.000 description 5
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 4
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- -1 keto steroids Chemical class 0.000 description 4
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- JYYNAJVZFGKDEQ-UHFFFAOYSA-N 2,4-Dimethylpyridine Chemical compound CC1=CC=NC(C)=C1 JYYNAJVZFGKDEQ-UHFFFAOYSA-N 0.000 description 2
- VFEWURLNQZFEPK-QANZEPGUSA-N C[C@](CCC1)(CC2)[C@@H]1[C@H](CC1)[C@H]2[C@@](C)(CC(C2)Br)[C@@H]1C2(O)Br Chemical compound C[C@](CCC1)(CC2)[C@@H]1[C@H](CC1)[C@H]2[C@@](C)(CC(C2)Br)[C@@H]1C2(O)Br VFEWURLNQZFEPK-QANZEPGUSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DJPZSBANTAQNFN-UHFFFAOYSA-N Testosterone acetate Natural products C1CC2=CC(=O)CCC2(C)C2C1C1CCC(OC(=O)C)C1(C)CC2 DJPZSBANTAQNFN-UHFFFAOYSA-N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- DJPZSBANTAQNFN-PXQJOHHUSA-N testosterone acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)C)[C@@]1(C)CC2 DJPZSBANTAQNFN-PXQJOHHUSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 230000001548 androgenic effect Effects 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004227 thermal cracking Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DESCH3573D DE864255C (de) | 1942-11-14 | 1942-11-14 | Verfahren zur Herstellung von A4,5 ungesaettigten 3-Ketoverbindungen der Androstanreihe |
| DK296443A DK65338C (da) | 1942-11-14 | 1943-11-13 | Fremgangsmaade til Fremstilling af Δ<4,5>-umættede 3-Ketoforbindelser af Androstanrækken. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DESCH3573D DE864255C (de) | 1942-11-14 | 1942-11-14 | Verfahren zur Herstellung von A4,5 ungesaettigten 3-Ketoverbindungen der Androstanreihe |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE864255C true DE864255C (de) | 1953-01-22 |
Family
ID=7423818
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DESCH3573D Expired DE864255C (de) | 1942-11-14 | 1942-11-14 | Verfahren zur Herstellung von A4,5 ungesaettigten 3-Ketoverbindungen der Androstanreihe |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE864255C (da) |
| DK (1) | DK65338C (da) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE160829C (da) * |
-
1942
- 1942-11-14 DE DESCH3573D patent/DE864255C/de not_active Expired
-
1943
- 1943-11-13 DK DK296443A patent/DK65338C/da active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE160829C (da) * |
Also Published As
| Publication number | Publication date |
|---|---|
| DK65338C (da) | 1947-01-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE864255C (de) | Verfahren zur Herstellung von A4,5 ungesaettigten 3-Ketoverbindungen der Androstanreihe | |
| AT257060B (de) | Verfahren zur Herstellung von neuen 3-Enoläthern der 6-Methyl-3-oxo-Δ<4>-steroide der Androstan-, 19-Norandrostan-, Pregnan- und 19-Norpregnanreihe | |
| DE1122944B (de) | Verfahren zur Herstellung von 1ª‡-Methyl-3-ketosteroiden | |
| DE752690C (de) | Verfahren zur Herstellung von Verbindungen der Cortinreihe | |
| DE864257C (de) | Verfahren zur Herstellung hormonal wirksamer Verbindungen der Oestranreihe | |
| DE935969C (de) | Verfahren zur Herstellung von ª‡, ª‰-ungesaettigten Steroidketonen | |
| DE737419C (de) | Verfahren zur Darstellung ungesaettigter Abkoemmlinge von Verbindungen der Cyclopentanopolyhydrophenanthren-Reihe | |
| AT267079B (de) | Verfahren zur Herstellung eines neuen Östradiolesters | |
| AT162906B (de) | Verfahren zur Herstellung von Derivaten der Cyclopentano-polyhydro-phenantren- bzw. der Polyhydro-chrysen-Reihe | |
| DE763488C (de) | Verfahren zur Umwandlung von gesaettigten und ungesaettigten 3-Oxy-17-Ketonen der Cyclopentanophenanthrenreihe in die Isomeren 17-Oxy-3-Ketone | |
| AT164549B (de) | Verfahren zur Herstellung von Sterinabbauprodukten | |
| DE737539C (de) | Verfahren zur Herstellung von Pregn-4-en-3, 20-dionderivaten, die 21-Stellung mit Sauerstoff substituiert sind | |
| DE870409C (de) | Verfahren zur Herstellung von 3-Ketonen der Androstan- und der Pregnanreihe | |
| DE1043333B (de) | Verfahren zur Herstellung von Methylsteroiden | |
| DE923187C (de) | Verfahren zur Herstellung von Pregnanverbindungen | |
| AT239455B (de) | Verfahren zur Herstellung neuer 17α-Acyloxy-6-methyl-16-methylenpregna-4,6-dien-3,20-dione | |
| DE869069C (de) | Verfahren zur Darstellung von im Ring A aromatischen Verbindungen der Oestranreihe | |
| DE1040546B (de) | Verfahren zur Herstellung von ungesaettigten, gegebenenfalls Brom enthaltenden Steroidverbindungen der Androstan- und Pregnanreihe | |
| AT232203B (de) | Verfahren zur Herstellung von 3β-Hydroxy-6-methyl-Δ<5>-steroiden | |
| DE725280C (de) | Verfahren zur Herstellung von Verbindungen der Cyclopentanopolyhydrophenanthrenreihe | |
| DE928832C (de) | Verfahren zur UEberfuehrung der Ketogruppe von Monoketonen der Cyclopentanopolyhydrophenanthrenreihe in eine veresterte Hydroxylgruppe | |
| AT160824B (de) | Verfahren zur Darstellung ungesättigter Oxyketone der Cyclopentanopolyhydrophenanthrenreihe. | |
| DE737420C (de) | Verfahren zur Darstellung von Ketonen der Cyclopentanopolyhydrophenanthrenreihe | |
| DE1793676C2 (de) | Verfahren zur Herstellung von Delta 4-bzw. Delta 5-ungesättigten Steroiden der Androstan-, Pregnan- und Sapogeninreihe mit einer Carboxylgruppe in 19-Stellung | |
| DE722409C (de) | Verfahren zur Oxydation ungesaettigter Alkohole der Cyclopentanopolyhydrophenanthrenreihe |