CH242609A - Process for the preparation of a new oxyhydrophenanthrene derivative. - Google Patents
Process for the preparation of a new oxyhydrophenanthrene derivative.Info
- Publication number
- CH242609A CH242609A CH242609DA CH242609A CH 242609 A CH242609 A CH 242609A CH 242609D A CH242609D A CH 242609DA CH 242609 A CH242609 A CH 242609A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- methyl
- derivative
- new
- carboxylic acid
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C62/30—Unsaturated compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C62/30—Unsaturated compounds
- C07C62/34—Unsaturated compounds containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C69/757—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines neuen Ogyhydrophenanthren-Derlvates. Es wurde gefunden, dass man zu einem neuen Ogyhydrophenanthren-Derivat gelan gen kann, wenn man eine 1-Äthyliden-2- methyl - 7 - methogy-1,2,3,4 - tetrahydrophen- anthren-2-carbonsäure zwecks Überführung der Äthylidengruppierung in einen Äthylrest mit hydrierenden Mitteln behandelt.
Für die Überführung der Äthylidengrup- pierung in den Äthylrest kann beispielsweise die katalytische Hydrierung dienen.
Das noch nicht bekannte Endprodukt des Verfahrens, die 1-Äthyl-2-methyl-7-methogy- 1,2,3,4-tetrahydrophenanthren-2-carbonsäure vom F.228-230 , zeigt sowohl bei paren- teraler als auch bei oraler Applikation eine ausserordentlich hohe östrogene Wirkung. Es soll therapeutische Verwendung finden oder als Zwischenprodukt zur Herstellung thera peutisch verwendbarer Verbindungen dienen.
<I>Beispiel:</I> 6 Gewichtsteile 1-Äthyliden-2-methyl-7- methogy -1,2;3,4 - tetrahydrophenanthren - 2 - carbonsäure vom F. 213 bis 215 der Formel.
EMI0001.0032
(erhalten z.
B. aus 1-geto-2-methyl-7-me- thogy -1,2,3,4- tetrahydrophenanthren- 2 - car- bonsäure-methylester durch Grignardierung mit Äthyl-magnesiumbromid, Wasserabspal tung aus dem so erhaltenen 1-Äthyl-l-ogy-2- methyl - 7 - methogy-1,2,3,4-tetrahydrophen- anthren-2-carbonsäure-methylestervomF.153 und anschliessende Verseifuug mit Kalium- hydrogyd bei 160 )
schüttelt man bei 50 in. einer Lösung von 250 Volumenteilen Was ser und 8 Gewichtsteilen Natriumhydrogyd mit 5 Gewichtsteilen eines Nickelkatalysators unter Wasserstoff. Nach der Aufnahme der für 1 Moläquivalent entsprechenden Menge Wasserstoff wird vom Katalysator abfiltriert und das Filtrat mit Mineralsäure angesäuert.
Man nimmt in Äther auf, trocknet die Äther- lösung und dampft ein. Durch Umkristalli- sieren des Rückstandes aus einem Aceton-Me- thylalkohol-Gemisch erhält man die östrogen- wirksame 1-Äthyl - 2 - methyl - 7 - methogy- 1,2,3,4-tetrahydrophenanthren-2 -carbonsäure der Formel
EMI0002.0016
in Form farbloser Kristalle vom F.
228 bis 230' nebst einer geringen. Menge eines un wirksamen -Diastereoisomeren vom F, 204 bis 200'.
Process for the production of a new ogyhydrophenanthrene derivative. It has been found that a new ogyhydrophenanthrene derivative can be obtained if a 1-ethylidene-2-methyl-7-methogy-1,2,3,4-tetrahydrophen-anthrene-2-carboxylic acid is used to convert the ethylidene group treated into an ethyl residue with hydrogenating agents.
Catalytic hydrogenation, for example, can be used to convert the ethylidene group into the ethyl radical.
The as yet unknown end product of the process, the 1-ethyl-2-methyl-7-methogy-1,2,3,4-tetrahydrophenanthrene-2-carboxylic acid from F.228-230, shows both parenteral and oral application has an extraordinarily high estrogenic effect. It should find therapeutic use or serve as an intermediate for the preparation of therapeutically useful compounds.
<I> Example: </I> 6 parts by weight of 1-ethylidene-2-methyl-7-methogy -1,2; 3,4 - tetrahydrophenanthrene - 2 - carboxylic acid with a melting point of 213 to 215 of the formula.
EMI0001.0032
(received e.g.
B. from 1-geto-2-methyl-7-methogy -1,2,3,4-tetrahydrophenanthrene- 2 - carboxylic acid methyl ester by Grignardation with ethyl magnesium bromide, elimination of water from the 1-ethyl thus obtained -l-ogy-2- methyl - 7 - methogy-1,2,3,4-tetrahydrophen- anthrene-2-carboxylic acid methyl ester from F.153 and subsequent saponification with potassium hydrogyd at 160)
is shaken at 50 in. A solution of 250 parts by volume of water and 8 parts by weight of sodium hydrogen with 5 parts by weight of a nickel catalyst under hydrogen. After the amount of hydrogen corresponding to 1 molar equivalent has been taken up, the catalyst is filtered off and the filtrate is acidified with mineral acid.
One takes up in ether, the ether solution is dried and evaporated. Recrystallization of the residue from an acetone-methyl alcohol mixture gives the estrogen-active 1-ethyl-2-methyl-7-methogy-1,2,3,4-tetrahydrophenanthrene-2-carboxylic acid of the formula
EMI0002.0016
in the form of colorless crystals from F.
228 to 230 'plus a small one. Amount of an ineffective -diastereoisomer of F, 204 to 200 '.
Claims (1)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH242609T | 1944-01-10 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH242609A true CH242609A (en) | 1946-05-31 |
Family
ID=4463052
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH242609D CH242609A (en) | 1944-01-10 | 1944-01-10 | Process for the preparation of a new oxyhydrophenanthrene derivative. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH242609A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1049855B (en) * | 1959-02-05 | CIBA Aktiengesellschaft, Base' (Schweiz) | Process for the preparation of methylenehydrophenanthrenes |
-
1944
- 1944-01-10 CH CH242609D patent/CH242609A/en unknown
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1049855B (en) * | 1959-02-05 | CIBA Aktiengesellschaft, Base' (Schweiz) | Process for the preparation of methylenehydrophenanthrenes |
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