DE841145C - Process for the preparation of the dipropargyl ether of 4, 4'-dioxy-ª ‡, ª ‰ -diaethylstilbene - Google Patents

Process for the preparation of the dipropargyl ether of 4, 4'-dioxy-ª ‡, ª ‰ -diaethylstilbene

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Publication number
DE841145C
DE841145C DEF2141A DEF0002141A DE841145C DE 841145 C DE841145 C DE 841145C DE F2141 A DEF2141 A DE F2141A DE F0002141 A DEF0002141 A DE F0002141A DE 841145 C DE841145 C DE 841145C
Authority
DE
Germany
Prior art keywords
dioxy
preparation
diaethylstilbene
dipropargyl ether
diethylstilbene
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
Application number
DEF2141A
Other languages
German (de)
Inventor
Alfred Dr Distelmaier
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Bayer 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 Bayer AG filed Critical Bayer AG
Priority to DEF2141A priority Critical patent/DE841145C/en
Application granted granted Critical
Publication of DE841145C publication Critical patent/DE841145C/en
Expired legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/075—Ethers or acetals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Steroid Compounds (AREA)

Description

Verfahren zur Herstellung des Dipropargyläthers des 4, 4'-Dioxy-a,,B-diäthylstilbens Der Dimethyläther des 4, 4'-Dioxy-a, ß-diäthylstilbens hat bereits praktische Anwendung als protaliiert wirksames Hormonpräparat gefunden. Trotzdem war ein Präparat erwünscht, das bei hoher Dosierung eine noch länger andauernde Hormonwirkung entfaltet, ohne unerwünschte Nebenerscheinungen zu zeigen.Process for the preparation of the dipropargyl ether des 4,4'-dioxy-a ,, B-diethylstilbene The dimethyl ether of 4,4'-dioxy-a, ß-diethylstilbene is already in practical use found as a protaliating effective hormone preparation. Nevertheless, a preparation was desired which, at high doses, develops an even longer lasting hormonal effect, without to show undesirable side effects.

Es wurde gefunden, daß ein solcher Stoff erhalten wird, wenn man nach an sich üblichen Arbeitsweisen den Dipropargyläther des 4, 4'-Dioxy-a, ß-diäthylstilbens herstellt. Zweckmäßig werden hierbei Salze des 4, 4'-Dioxy-oc, ß-diäthylstilbens mit reaktionsfähigen Estern des Propargylalkohols umgesetzt. Als reaktionsfähige Ester kommen in erster Linie Halogenwasserstoffester oder Ester aliphatischer oder aromatischer Sulfonsäuren in Frage. Der Dipropargyläther des 4, 4'-Dioxy-x,ß-diäthylstilbens stellt ein Kristallpulver vom Schmelzpunkt io6 bis io7° dar, das sich leicht in Öl löst und in dieser Form zu Injektionen verwendet werden kann. Beispiel i 5 g des Natriumsalzes des 4, 4'-Dioxy-x, ß-diäthylstilbens werden in einem Gemisch aus Äthylalkohol und Aceton gelöst. Nach Zutropfen von 5 g Propargylbromid erhitzt man i Stunde auf dem Wasserbad, kühlt ab und destilliert die Lösungsmittel unter vermindertem Druck ab. Der Rückstand wird zuerst mit Wasser und später mit 0,5 n-Natronlauge verrührt und schließlich aus Äthylalkohol umkristallisiert. Der entstandene Dipropargyläther des 4, 4'-Dioxy-a,ßdiäthylstilbens schmilzt bei 1o6 bis 1070.It has been found that such a substance is obtained if the dipropargyl ether of 4,4'-dioxy-a, ß-diethylstilbene is prepared by conventional procedures. In this case, salts of 4,4'-dioxy-oc, ß-diethylstilbene are expediently reacted with reactive esters of propargyl alcohol. Possible reactive esters are primarily hydrogen halide esters or esters of aliphatic or aromatic sulfonic acids. The dipropargyl ether of 4,4'-dioxy-x, ß-diethylstilbene is a crystal powder with a melting point of 10 ° to 10 °, which dissolves easily in oil and can be used in this form for injections. Example i 5 g of the sodium salt of 4,4'-dioxy-x, ß-diethylstilbene are dissolved in a mixture of ethyl alcohol and acetone. After 5 g of propargyl bromide have been added dropwise, the mixture is heated on a water bath for 1 hour, cooled and the solvent is distilled off under reduced pressure. The residue is first stirred with water and later with 0.5 N sodium hydroxide solution and finally recrystallized from ethyl alcohol. The resulting dipropargyl ether of 4,4'-dioxy-a, ßdiethylstilbene melts at 106 to 1070.

Beispiel 2 5 g 4.4'-Dioxy-ac,ß-diäthylstilben werden mit 5,2 g Kaliumcarbonat in ioo ccm Aceton 2 Stunden unter Rückfluß erhitzt. Nach dem Abkühlen wird eine Mischung aus 5 g Propargylbromid und 20 ccm Aceton zugetropft und die Reaktionsmischung anschließend 6 Stunden zum Sieden erhitzt. Nach dem Absaugen des Rückstandes wird die Lösung, wie im Beispiel z beschrieben, aufgearbeitet.Example 2 5 g of 4,4'-dioxy-ac, ß-diethylstilbene are mixed with 5.2 g of potassium carbonate heated under reflux in 100 cc of acetone for 2 hours. After cooling down, a Mixture of 5 g propargyl bromide and 20 ccm acetone was added dropwise and the reaction mixture then heated to boiling for 6 hours. After the residue has been filtered off with suction the solution, as described in example z, worked up.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung des Dipropargyläthers des 4, 4'-Dioxy-a, ß-diäthylstilbens, dadurch gekennzeichnet, daß man Salze des 4,4'-Dioxy-a,ßdiäthylstilbens mit reaktionsfähigen Estern des Propargylalkohols in an sich üblicher Weise umsetzt. Claim: Process for the preparation of the dipropargyl ether of 4, 4'-dioxy-a, ß-diethylstilbene, characterized in that salts of 4,4'-dioxy-a, ßdiethylstilbene are reacted with reactive esters of propargyl alcohol in a conventional manner.
DEF2141A 1950-07-23 1950-07-23 Process for the preparation of the dipropargyl ether of 4, 4'-dioxy-ª ‡, ª ‰ -diaethylstilbene Expired DE841145C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEF2141A DE841145C (en) 1950-07-23 1950-07-23 Process for the preparation of the dipropargyl ether of 4, 4'-dioxy-ª ‡, ª ‰ -diaethylstilbene

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF2141A DE841145C (en) 1950-07-23 1950-07-23 Process for the preparation of the dipropargyl ether of 4, 4'-dioxy-ª ‡, ª ‰ -diaethylstilbene

Publications (1)

Publication Number Publication Date
DE841145C true DE841145C (en) 1952-06-13

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Family Applications (1)

Application Number Title Priority Date Filing Date
DEF2141A Expired DE841145C (en) 1950-07-23 1950-07-23 Process for the preparation of the dipropargyl ether of 4, 4'-dioxy-ª ‡, ª ‰ -diaethylstilbene

Country Status (1)

Country Link
DE (1) DE841145C (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2748169A (en) * 1950-07-22 1956-05-29 Schenley Ind Inc Novel chemotherapeutic agents comprising dialkynyl ethers of diethylstilbestrol
EP0293768A1 (en) * 1987-06-01 1988-12-07 The Dow Chemical Company Process for making propargyl ethers of hydroxyaromatic compounds

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2748169A (en) * 1950-07-22 1956-05-29 Schenley Ind Inc Novel chemotherapeutic agents comprising dialkynyl ethers of diethylstilbestrol
EP0293768A1 (en) * 1987-06-01 1988-12-07 The Dow Chemical Company Process for making propargyl ethers of hydroxyaromatic compounds

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