NO129299B - - Google Patents
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- Publication number
- NO129299B NO129299B NO169877A NO16987767A NO129299B NO 129299 B NO129299 B NO 129299B NO 169877 A NO169877 A NO 169877A NO 16987767 A NO16987767 A NO 16987767A NO 129299 B NO129299 B NO 129299B
- Authority
- NO
- Norway
- Prior art keywords
- androstane
- oxo
- methyl
- general formula
- pregnane series
- Prior art date
Links
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- QZLYKIGBANMMBK-UGCZWRCOSA-N 5α-Androstane Chemical compound C([C@@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CCC[C@@]2(C)CC1 QZLYKIGBANMMBK-UGCZWRCOSA-N 0.000 claims description 7
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 150000003431 steroids Chemical class 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 150000003128 pregnanes Chemical class 0.000 claims description 5
- 238000010992 reflux Methods 0.000 claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- JWMFYGXQPXQEEM-NUNROCCHSA-N 5β-pregnane Chemical compound C([C@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](CC)[C@@]2(C)CC1 JWMFYGXQPXQEEM-NUNROCCHSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- MDDPTCUZZASZIQ-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]alumane Chemical compound [Al+3].CC(C)(C)[O-].CC(C)(C)[O-].CC(C)(C)[O-] MDDPTCUZZASZIQ-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000003263 anabolic agent Substances 0.000 description 1
- 230000001195 anabolic effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000006345 epimerization reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000583 progesterone congener Substances 0.000 description 1
Landscapes
- Steroid Compounds (AREA)
Description
Fremgangsmåte til fremstilling av terapeutisk virksomme 6a-metyl-3-oxo-A<4->steroider av androstan og pregnanrekkene. Process for the production of therapeutically effective 6a-methyl-3-oxo-A<4->steroids from the androstane and pregnane series.
Foreliggende oppfinnelse angår en fremgangsmåte til fremstilling av 6a-metyl-3-oxo-A<4->steroider av androstan- og pregnan The present invention relates to a process for the production of 6a-methyl-3-oxo-A<4->steroids from androstane and pregnane
-rekkene. - the ranks.
Ved hjelp av fremgangsmåten ifølge Using the method according to
oppfinnelsen kan der fremstilles nye for-bindelser av androstan- og pregnanrekkene som er verdifulle på grunn av deres biologiske egenskaper (f. eks. som anaboliske eller progestasjonale midler) eller som mel-lomprodukter ved fremstilling av forbin-delser med verdifulle biologiske egenskaper. the invention, new compounds of the androstane and pregnane series can be produced which are valuable because of their biological properties (e.g. as anabolic or progestational agents) or as intermediate products in the production of compounds with valuable biological properties.
Et vesentlig karakteristisk trekk ved fremgangsmåten ifølge oppfinnelsen til fremstilling av 6a-metyl-3-oxo-A<4->steroider av androstan- og pregnanrekkene med den generelle formel: A significant characteristic feature of the process according to the invention for the production of 6a-methyl-3-oxo-A<4->steroids of the androstane and pregnane series with the general formula:
i hvilken X betegner en av gruppene I eller in which X denotes one of the groups I or
er at man be- is that one beg-
i in
handler et 3(3 : 5a-dihydroxy-6(3-metylste-roider av androstan- og pregnanrekkene med den generelle formel: is a 3(3:5a-dihydroxy-6(3-methylsteroid of the androstane and pregnane series) with the general formula:
(hvor X har den ovenfor angitte betydning) (where X has the above meaning)
med et aluminiumalkoholat i en blanding av cykloheksanon og toluen under opp-varming med tilbakeløpskjøling. Når man f. eks. bruker aluminium-tertiært-butoxyd i en blanding av cykloheksanon og toluen (dvs. Oppenauers oxydasjonsmiddel), og with an aluminum alcoholate in a mixture of cyclohexanone and toluene under reflux heating. When you e.g. uses aluminum tertiary butoxide in a mixture of cyclohexanone and toluene (i.e., Oppenauer's oxidizing agent), and
oppvarmer under tilbakeløpskjøling, inn-treffer oxydasjonen i 3-stillingen sammen med avvanning av hydroxyl-gruppen i 5a-stillingen, så at man får et 6|3-metyl-3-oxo-A<4->steroid, som undergår epimeriser-ing ved kullstoffatomet i 6-stillingen, så at man får 6a-metyl-3-oxo-A<4->steroidet. heated under reflux, the oxidation occurs in the 3-position together with dehydration of the hydroxyl group in the 5a-position, so that a 6|3-methyl-3-oxo-A<4->steroid is obtained, which undergoes epimerization ing at the carbon atom in the 6-position, so that you get the 6a-methyl-3-oxo-A<4->steroid.
I det følgende beskrive^ som eksempel en utførelsesform for fremgangsmåten ifølge oppfinnelsen. In the following, an embodiment of the method according to the invention is described as an example.
Eksempel. Example.
17|3-hydroxy-6a : 17a-dimetylandrost-4-en-3-on. 17|3-hydroxy-6a : 17a-dimethylandrost-4-en-3-one.
En oppløsning av 6(3 : 17a-dimetyl-androstan-3|3 : 5a : 17|3-triol (1,2 g) i cykloheksanon (8,2 ml) ble tilsatt til en opp-løsning av aluminium-tertiært-butoxyd To a solution of aluminum tertiary- butoxide
(1,1 g) i toluen (5 ml) og blandingen ble (1.1 g) in toluene (5 ml) and the mixture was
oppvarmet under tilbakeløpskjøling i 45 heated under reflux for 45
minutter. Benzen (ca. 50 ml) ble tilsatt og minutes. Benzene (about 50 ml) was added and
oppløsningen vasket med fortynnet svovel-syre og vann. Oppløsningen ble derpå des-tillert med damp i 4 timer, hvorpå den ble the solution washed with dilute sulfuric acid and water. The solution was then distilled with steam for 4 hours, after which it became
ekstrahert med eter. Ekstraktet ble vasket extracted with ether. The extract was washed
med vann, tørket og inndampet. Man lot with water, dried and evaporated. Man pretended
residuet i benzen gå gjennom en alumini-umoxydsøyle (10 g) og det resulterende the residue in benzene pass through an aluminum oxide column (10 g) and the resulting
oljeaktige produkt ble krystallisert fra en oily product was crystallized from a
blanding av aceton og heksan. Herved skilte mixture of acetone and hexane. Hereby signed
17(3-hydroxy-6a : 17a - dimetylandrost-4-en-3-on (6a-dimetyltestosteron) seg ut 17(3-hydroxy-6a : 17a - dimethylandrost-4-en-3-one (6a-dimethyltestosterone)
i form av nåler. Sm.p. 134—135° C. in the form of needles. Sm.p. 134-135° C.
23° 23°
[a] D = + 49° (c, 0,421 i etanol), [a] D = + 49° (c, 0.421 in ethanol),
l maks. m\ i (4,19) i isopropanol. l max. m\ in (4.19) in isopropanol.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO169877A NO129299B (en) | 1961-07-21 | 1967-09-26 |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB26488/61A GB940488A (en) | 1961-07-21 | 1961-07-21 | Penicillins |
| GB26489/61A GB940489A (en) | 1961-07-21 | 1961-07-21 | Penicillins |
| NO14502962A NO124690B (en) | 1961-07-21 | 1962-07-06 | |
| NO169877A NO129299B (en) | 1961-07-21 | 1967-09-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO129299B true NO129299B (en) | 1974-03-25 |
Family
ID=27448690
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO169877A NO129299B (en) | 1961-07-21 | 1967-09-26 |
Country Status (1)
| Country | Link |
|---|---|
| NO (1) | NO129299B (en) |
-
1967
- 1967-09-26 NO NO169877A patent/NO129299B/no unknown
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