CH184419A - Process for the preparation of a mixture of stereoisomeric dihydrofollicle hormones of the formula C18H24O2. - Google Patents

Process for the preparation of a mixture of stereoisomeric dihydrofollicle hormones of the formula C18H24O2.

Info

Publication number
CH184419A
CH184419A CH184419DA CH184419A CH 184419 A CH184419 A CH 184419A CH 184419D A CH184419D A CH 184419DA CH 184419 A CH184419 A CH 184419A
Authority
CH
Switzerland
Prior art keywords
mixture
formula
hormones
dihydrofollicle
stereoisomeric
Prior art date
Application number
Other languages
German (de)
Inventor
Schering-Kahlbaum A G
Original Assignee
Schering Kahlbaum Ag
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Schering Kahlbaum Ag filed Critical Schering Kahlbaum Ag
Publication of CH184419A publication Critical patent/CH184419A/en

Links

Landscapes

  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

  

  Verfahren zur Herstellung eines Gemisches     stereoisornerer        Dihydrofollikelhormone     der Formel     CisH2402.            Gegenstand    vorliegenden Patentes ist ein  Verfahren zur Herstellung eines     Gemisches          stereoisomerer        Dihydrofollikelhormone    der  Formel     ClR'Ì.,402,    das .dadurch gekennzeich  net ist,

   dass man das Gemisch der     Oxime     der     isomeren        Follikelhormone    der Formel       C1811220_    mit einem reduzierenden Mittel  und das entstandene     Amingemisch    bei Ge  genwart     einer    Säure mit einem Nitrit be  handelt.  



  Das so erhältliche Produkt, das bereits  im Schweiz. Patent Nr. 177408     beschrieben     wurde, soll als     Arzneimittel        Verwendung     finden.    <I>Beispiel:</I>    0,5 g des von     Butenandt    beschriebenen  Gemisches der     Oxime    der     isomeren    Follikel  hormone der Formel     C1RH.202    werden in Al  kohol gelöst und zum Sieden erhitzt.

   Dann       wird    nach und nach 1 g fein     geschnitttenes          Natriummetall    in die .siedende Lösung ein-         getragen,    nach vollendeter Lösung .des Na  triums mit Wasser     verdünnt    und durch Ein  engen im Vakuum der Alkohol aus der Lö  sung entfernt.

   Ohne das entstandene     Amin-          g        o        emisch        zu        isolieren,        wird        nun        mit        verdünn-          ter    Salzsäure angesäuert und mit     einer    Auf  lösung von     0,25g        galiumnitrit    in Wasser  versetzt und aufgekocht.

   Aus der sauren Lö  sung wird mit Äther das Reaktionsprodukt       ausgeschüttelt,    ,das nach .dem Verdunstendes  Äthers .als ölige, .schwach braun gefärbte  Masse zurückbleibt. Durch     Umkristallisieren     kann man aus dem     Stereoisomerengemisch     das schon beschriebene     Stereoisomere    des     Di-          hydrofollikelhormons    der     Formel        C1811240::     mit dem Schmelzpunkt von 168 bis 170   und  der typischen Fluoreszenz der schwefelsauren  Lösung in     ultraviolett        isolieren.  



  Process for the preparation of a mixture of stereoisomeric dihydrofollicle hormones of the formula CisH2402. The subject of the present patent is a process for the preparation of a mixture of stereoisomeric dihydrofollicle hormones of the formula ClR'Ì., 402, which is marked thereby,

   that the mixture of the oximes of the isomeric follicle hormones of the formula C1811220_ is treated with a reducing agent and the amine mixture formed is treated with a nitrite in the presence of an acid.



  The product available in this way, which is already available in Switzerland. Patent No. 177408 is said to find use as a medicament. <I> Example: </I> 0.5 g of the mixture of oximes of the isomeric follicle hormones of the formula C1RH.202 described by Butenandt is dissolved in alcohol and heated to the boil.

   Then gradually 1 g of finely chopped sodium metal is introduced into the boiling solution, after the sodium has dissolved, it is diluted with water and the alcohol is removed from the solution by concentrating it in vacuo.

   Without isolating the amine produced, it is now acidified with dilute hydrochloric acid, a solution of 0.25 g of galium nitrite in water is added and the mixture is boiled.

   The reaction product is shaken out of the acidic solution with ether, and after the ether has evaporated it remains as an oily, pale brown colored mass. The already described stereoisomer of the dihydrofollicle hormone of the formula C1811240 :: with a melting point of 168 to 170 and the typical fluorescence of the sulfuric acid solution in ultraviolet can be isolated from the stereoisomer mixture by recrystallization.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Ge misches stereoisomerer Dihydrofollikelhor- morse der Formel C1aH2402, dadurch gekenn zeichnet, dass man das Gemisch der Ogime der isomeren Follikelhormone der Formel C"H"02 ,mit einem reduzierenden Mittel, und das entstandene Amingemisch bei Gegen wart einer Säure mit einem Nitrit behandelt. PATENT CLAIM: Process for the production of a mixture of stereoisomeric dihydrofollicle hormones of the formula C1aH2402, characterized in that the mixture of the ogime of the isomeric follicle hormones of the formula C "H" 02, with a reducing agent, and the amine mixture formed in the presence of one Acid treated with a nitrite.
CH184419D 1932-12-23 1933-10-24 Process for the preparation of a mixture of stereoisomeric dihydrofollicle hormones of the formula C18H24O2. CH184419A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE184419X 1932-12-23

Publications (1)

Publication Number Publication Date
CH184419A true CH184419A (en) 1936-05-31

Family

ID=5719004

Family Applications (1)

Application Number Title Priority Date Filing Date
CH184419D CH184419A (en) 1932-12-23 1933-10-24 Process for the preparation of a mixture of stereoisomeric dihydrofollicle hormones of the formula C18H24O2.

Country Status (1)

Country Link
CH (1) CH184419A (en)

Similar Documents

Publication Publication Date Title
CH184419A (en) Process for the preparation of a mixture of stereoisomeric dihydrofollicle hormones of the formula C18H24O2.
DE574838C (en) Process for the preparation of cyclic glycols and their derivatives or of ketones
AT160403B (en) Process for the preparation of isomer mixtures of estradiol or lower hydrogen analogues thereof or their derivatives.
AT160275B (en) Process for the preparation of esters of pregnen- (5) -ol- (3) -one- (20).
AT225176B (en) Process for the preparation of new hydrazine derivatives
AT159425B (en) Process for the preparation of alkyl ethers of resorcinol monocarbonic acid diethylamide or its homologues.
AT237596B (en) Process for the preparation of the new 1-cyclohexyl-2-aminopropanos- (1) and its salts
AT92407B (en) Process for the preparation of 1-allyl-3,7-dimethylxanthine.
DE711378C (en) Method for the preparation of the dihydrofollicle hormone
AT160612B (en) Process for the preparation of androstanol- (3) -one- (17) or of androstandiol- (3.17) or their stereoisomers.
AT217027B (en) Process for the preparation of new α-aminoisobutyrophenone compounds and their acid addition salts
AT235262B (en) Process for the preparation of trans-decen- (2) -one- (9) -acid- (1)
CH195775A (en) Process for the preparation of a new ester.
CH345885A (en) Process for the preparation of 1-ketocyclooctyl-2-acetic acid
CH242289A (en) Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid.
CH136040A (en) Process for the preparation of a new dye intermediate.
CH183330A (en) Process for the preparation of a mixture of isomeric acyloctahydrofollicle hormones.
CH179975A (en) Process for the preparation of an acylated dihydrofollicle hormone.
CH284072A (en) Process for the preparation of 3,4-dimethyl-5-phenyl-2-imino-thiazolidine.
CH269340A (en) Process for the representation of a basic ether.
CH196648A (en) Process for the preparation of 3-acetyl-17-benzoyl-trans-androstandiol-3,17.
CH233347A (en) Process for the preparation of a new quaternary pyridinium chloride.
CH235496A (en) Process for the production of a sugar derivative.
CH187935A (en) Process for the preparation of an acridinium compound.
CH137948A (en) Process for the preparation of a carboxyamidobenzene-o-thioglycolic acid.