CH184532A - Process for the preparation of a mixture of isomeric acyloctahydrofollicle hormones. - Google Patents
Process for the preparation of a mixture of isomeric acyloctahydrofollicle hormones.Info
- Publication number
- CH184532A CH184532A CH184532DA CH184532A CH 184532 A CH184532 A CH 184532A CH 184532D A CH184532D A CH 184532DA CH 184532 A CH184532 A CH 184532A
- Authority
- CH
- Switzerland
- Prior art keywords
- mixture
- hormones
- isomeric
- preparation
- acyloctahydrofollicle
- Prior art date
Links
- 229940088597 hormone Drugs 0.000 title claims description 10
- 239000005556 hormone Substances 0.000 title claims description 10
- 239000000203 mixture Substances 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 125000003198 secondary alcohol group Chemical group 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
Description
Verfahren zur Darstellung eines Gemisches isomerer Aeyloctahydrofollikelhormone. Gegenstand vorliegenden Patentes ist ein Verfahren zur Darstellung eines Gemisches dei, i soni eren hon oh exahydrobenzoyl octahyd ro- follikelhormone, das dadurch gekennzeichnet ist, dass man ein Gemisch der beiden isomeren Monobenzoyldihydi,ofollikelhormone mit kata lytisch erregtem Wasserstoff unter Bedin gungen behandelt,
bei denen der Benzolkern hydriert wird.
Zweckmässig geschieht die Durchführung der Hydrierung durch Zufuhr von Wasser stoff bei Gegenwart von Katalysatoren; am besten in Anwesenheit eines Lösungsmittels. <I>Beispiel:</I> ä g der Monobenzoylderivate des Dibydro- follikelhormonisomerengemisches, so wie es bei der Reduktion der Ketogruppe des e ol- likelhormons zur sekundären Alkoholgruppe erhalten wird, werden mit der gleichen Menge eines vorreduzierten Nickelkatalysa- tors (mit Zusätzen von Kupfer und Kobalt)
bei einem Wasserstoffdruck von 100 Atmo sphären im Autoklaven auf ca.<B>180'</B> erhitzt. Nach beendeter Wasserstoffaufnahme wird die vom Katalysator befreite Reaktionslösung zur Trockne abgedampft. Das erhaltene Hy- drierungsprodukt, ein Gemisch isomerer Mo nohexahydrobenzoyloctahydrofollikelhbrmone, das als Arzneimittel Verwendung finden soll, besitzt harzige Konsistenz und kann durch Verseifung in ein Gemisch isomerer Octa- hydrofollikelhormone der Formel C18H8002 übergeführt werden.
Process for the preparation of a mixture of isomeric aeyloctahydrofollicle hormones. The subject of the present patent is a process for the preparation of a mixture of the iosonic hon oh exahydrobenzoyl octahydrofollicle hormones, which is characterized in that a mixture of the two isomeric monobenzoyldihydric, ofollicular hormones is treated with catalytically excited hydrogen under conditions
in which the benzene nucleus is hydrogenated.
The hydrogenation is expediently carried out by supplying hydrogen in the presence of catalysts; best in the presence of a solvent. <I> Example: </I> ä g of the monobenzoyl derivatives of the dibydrofollicle hormone isomer mixture, as obtained in the reduction of the keto group of the oleic hormone to the secondary alcohol group, are treated with the same amount of a pre-reduced nickel catalyst (with additives of copper and cobalt)
heated to approx. <B> 180 '</B> at a hydrogen pressure of 100 atmospheres in the autoclave. After the uptake of hydrogen has ended, the reaction solution freed from the catalyst is evaporated to dryness. The hydrogenation product obtained, a mixture of isomeric monohexahydrobenzoyloctahydrofollicle hormones, which is to be used as a pharmaceutical, has a resinous consistency and can be converted into a mixture of isomeric octahydrofollicle hormones of the formula C18H8002 by saponification.
Claims (1)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DESCH101131D DE626291C (en) | 1933-05-06 | 1933-05-06 | Method for the preparation of acyloctahydrofollicle hormone |
| CH176487T | 1934-05-02 | ||
| DESCH104319D DE645818C (en) | 1933-05-06 | 1934-05-25 | Method for the preparation of acyloctahydrofollicle hormone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH184532A true CH184532A (en) | 1936-05-31 |
Family
ID=34108250
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH184532D CH184532A (en) | 1933-05-06 | 1934-05-02 | Process for the preparation of a mixture of isomeric acyloctahydrofollicle hormones. |
| CH184531D CH184531A (en) | 1933-05-06 | 1934-05-02 | Process for the preparation of a mixture of isomeric acyloctahydrofollicle hormones. |
| CH176487D CH176487A (en) | 1933-05-06 | 1934-05-02 | Method for the preparation of an acyloctahydrofollicle hormone. |
| CH185854D CH185854A (en) | 1933-05-06 | 1934-11-08 | Process for the preparation of a mixture of isomeric octahydrofollicle hormone diacetates. |
| CH186460D CH186460A (en) | 1933-05-06 | 1934-11-08 | Process for the preparation of a mixture of isomeric octahydrofollicle hormone acetates. |
Family Applications After (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH184531D CH184531A (en) | 1933-05-06 | 1934-05-02 | Process for the preparation of a mixture of isomeric acyloctahydrofollicle hormones. |
| CH176487D CH176487A (en) | 1933-05-06 | 1934-05-02 | Method for the preparation of an acyloctahydrofollicle hormone. |
| CH185854D CH185854A (en) | 1933-05-06 | 1934-11-08 | Process for the preparation of a mixture of isomeric octahydrofollicle hormone diacetates. |
| CH186460D CH186460A (en) | 1933-05-06 | 1934-11-08 | Process for the preparation of a mixture of isomeric octahydrofollicle hormone acetates. |
Country Status (1)
| Country | Link |
|---|---|
| CH (5) | CH184532A (en) |
-
1934
- 1934-05-02 CH CH184532D patent/CH184532A/en unknown
- 1934-05-02 CH CH184531D patent/CH184531A/en unknown
- 1934-05-02 CH CH176487D patent/CH176487A/en unknown
- 1934-11-08 CH CH185854D patent/CH185854A/en unknown
- 1934-11-08 CH CH186460D patent/CH186460A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH176487A (en) | 1935-04-15 |
| CH186460A (en) | 1936-09-15 |
| CH185854A (en) | 1936-08-15 |
| CH184531A (en) | 1936-05-31 |
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