CH270463A - Process for the production of a new hydrophenanthrene derivative. - Google Patents

Process for the production of a new hydrophenanthrene derivative.

Info

Publication number
CH270463A
CH270463A CH270463DA CH270463A CH 270463 A CH270463 A CH 270463A CH 270463D A CH270463D A CH 270463DA CH 270463 A CH270463 A CH 270463A
Authority
CH
Switzerland
Prior art keywords
methyl
ethyl
carboxylic acid
production
methoxy
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellschaft Ciba
Original Assignee
Ciba Geigy
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 Ciba Geigy filed Critical Ciba Geigy
Publication of CH270463A publication Critical patent/CH270463A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C35/22—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system
    • C07C35/37—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with a hydroxy group on a condensed system having three rings
    • C07C35/42—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with a hydroxy group on a condensed system having three rings derived from the phenanthrene skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
    • C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

      Verfahren    zur Herstellung eines neuen     Hydrophenanthrenderivates.       Es wurde gefunden, dass man zu einem  neuen     Hydrophenanthrenderivat    gelangen  kann, wenn man auf einen     n-7-lIethoxv        =2-me-          thyl        -1-ätliyl-1,    2,     3,

  4-tetr        ahydro-phenaiithren-2-          earbonsäure-thiolester    zwecks Überführung  des     Carbonsäurethiolester-Restes    in eine     0xy-          methy        1-(Truppe    in     Abwesenheit    von Wasser  einen mit. Wasserstoff beladenen Katalysator  einwirken lässt.  



  Das noch nicht     bekannte    Endprodukt, das       n-7-Methoxy-2-metliyl-l-ä.thyl-1,2,3,4-tetra.hy-          dro-phenanthryl-(2)-methanol    vom F. 100 bis  1030 zeigt sowohl bei     subcutaner    als auch bei  oraler Applikation eine ausserordentlich hohe       oestrogene    Wirkung. Es soll therapeutische  Verwendung finden oder als Zwischenprodukt  zur Herstellung therapeutisch verwendbarer  Verbindungen dienen.  



  Die Überführung des     Carbonsäurethiol-          ester-Restes    in eine     Oxymethylgruppe    wird  zum Beispiel mit Hilfe von     Raney-Nickel    in  Gegenwart von wasserfreiem Alkohol durch  geführt.  



  Die Ausgangsstoffe werden zum Beispiel  erhalten durch Umsetzung der     Säurehaloge-          nide    der     n-7-iiTethoxy-2-methyl-l-äthyl-1,2,3,4-          tetrahydro-phenanthren-2-earbonsäure    vom  F. 228 bis 2300 mit     Merkaptanen,    wie     Methyl-          merkaptan.     



       Beispiel:     0,3 Gewichtsteile n-7-l-lethoxy-2-niethyl       1-äthyl-1,2,3,4-tetrahydro-phenanthren-2-car-          bonsäure-thiolmethylester    wird in 12      'olum-          teilen        absolutem    Alkohol 6 Stunden in Gegen-    wart von 3,5 Gewichtsteilen     Raney-Niekel    ge  kocht.

   -Man filtriert ab, dampft das Filtrat ein,  kristallisiert den Rückstand aus verdünntem  Methanol um und erhält das     n-7-3Iethoxy        \_'-          methyl-l-äthyl-1,2,3,4-tetr        ahvdr        o-pheiianthry        1-          (2)        -methanol    der Formel  
EMI0001.0047     
    in Form glänzender Plättchen vom F. 56 bis       60     C, welche nach längerem Trocknen im       Hoclivahuum    bei 100 bis 1.030 C schmelzen.



      Process for the production of a new hydrophenanthrene derivative. It has been found that a new hydrophenanthrene derivative can be obtained if one uses an n-7-ethoxv = 2-methyl -1-ethyl-1, 2, 3,

  4-tetrahydro-phenethyl-2-carboxylic acid thiol ester for the purpose of converting the carboxylic acid thiol ester radical into an oxymethyl group in the absence of water allows a catalyst loaded with hydrogen to act.



  The as yet unknown end product, the n-7-methoxy-2-methyl-1-a-ethyl-1,2,3,4-tetra.hy- dro-phenanthryl- (2) -methanol with a melting point of 100 to 1030 shows an extraordinarily high estrogenic effect on both subcutaneous and oral administration. It should find therapeutic use or serve as an intermediate for the preparation of therapeutically useful compounds.



  The conversion of the carboxylic acid thiol ester residue into an oxymethyl group is carried out, for example, with the aid of Raney nickel in the presence of anhydrous alcohol.



  The starting materials are obtained, for example, by reacting the acid halides of n-7-ii-methoxy-2-methyl-1-ethyl-1,2,3,4-tetrahydro-phenanthrene-2-carboxylic acid with a melting point of 228 to 2300 with mercaptans such as methyl mercaptan.



       Example: 0.3 parts by weight of n-7-l-lethoxy-2-diethyl 1-ethyl-1,2,3,4-tetrahydro-phenanthrene-2-carboxylic acid thiolmethyl ester is converted into 12 ole parts of absolute alcohol 6 Cooked hours in the presence of 3.5 parts by weight of Raney-Niekel.

   - It is filtered off, the filtrate is evaporated, the residue is recrystallized from dilute methanol and the n-7-3Iethoxy \ _'-methyl-1-ethyl-1,2,3,4-tetr ahvdr o-pheiianthry 1- (2) -methanol of the formula
EMI0001.0047
    in the form of shiny platelets with a temperature of 56 to 60 ° C, which melt after prolonged drying in a Hoclive vacuum at 100 to 1030 ° C.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen Hy drophenanthrenderivates, dadurch gekenn zeichnet, dass man auf einen n-7-Methoxy- 2 - methyl -1. - äthyl -1,2,3,4-tetrahydro-phen- anthreii 2-carbonsäiire-tliiolester zwecks über- führung des Carbonsäurethiolester-Restes in eine Oxymethyl-Gruppe in Abwesenheit von Wasser einen mit. PATENT CLAIM: Process for the production of a new Hy drophenanthrenderivates, characterized in that one is on an n-7-methoxy- 2 - methyl -1. - Ethyl -1,2,3,4-tetrahydro-phenanthreii 2-carboxylic acid thiol ester for the purpose of converting the carboxylic acid thiol ester residue into an oxymethyl group in the absence of water with one. Wasserstoff beladenen Ka- ta.ltIsator einwirken lässt. Das noch nielit bekannte Endprodukt, das n - 7 -Methoxy -2 - methyl -1- äthyl-1,2,3,4-tetra- hydro-phenanthryl-(2)-methanol vom F. 100 bis 1.030, zeigt sowohl bei subcutaner als auch bei oraler Applikation eine ausserordentlich hohe oestrogene Wirkung. Es soll therapeu tische Verwendung finden oder als Zwischen- produkt zur Herstellung therapeutisch ver wendbarer Verbindungen dienen. Let the hydrogen-loaded catalytic converter act. The as yet unknown end product, the n-7-methoxy -2-methyl -1-ethyl-1,2,3,4-tetra-hydro-phenanthryl- (2) -methanol with a melting point of 100 to 1,030, shows both at Subcutaneous as well as oral administration an extraordinarily high estrogenic effect. It should find therapeutic use or serve as an intermediate product for the production of therapeutically usable compounds. UNTERANSPRÜCHE: 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man als mit Was serstoff beladenen Katalysator Raney-Nickel verwendet. 2. Verfahren nach Patentanspruch und Unteranspruch 1, dadurch gekennzeichnet, dass man n-7-Methoxy-2-methyl-l-äthyl-1,2,3,4- tetrahydro - phenanthren,- 2 -carbonsäure-thiol- methylester verwendet. SUBClaims: 1. The method according to claim, characterized in that Raney nickel is used as the catalyst loaded with hydrogen. 2. The method according to claim and dependent claim 1, characterized in that n-7-methoxy-2-methyl-1-ethyl-1,2,3,4-tetrahydro - phenanthrene, - 2-carboxylic acid-thiol-methyl ester is used.
CH270463D 1946-11-22 1946-11-22 Process for the production of a new hydrophenanthrene derivative. CH270463A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH270463T 1946-11-22
CH268161T 1946-11-22

Publications (1)

Publication Number Publication Date
CH270463A true CH270463A (en) 1950-08-31

Family

ID=25730991

Family Applications (1)

Application Number Title Priority Date Filing Date
CH270463D CH270463A (en) 1946-11-22 1946-11-22 Process for the production of a new hydrophenanthrene derivative.

Country Status (1)

Country Link
CH (1) CH270463A (en)

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