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17a-Ethynyl-19-nortestosterone

Reduction of 17a-Ethynyl-19-nortestosterone to 4,5a-Dihydro-17a-ethynyl-19-nortestosterone ... [Pg.52]

A solution of 17a-ethynyl-19-nortestosterone (15 g, 0.05 mole) in dioxane-ether (1 1, 250 ml) is added rapidly to a well stirred solution of lithium (2.25 g, 0.325 g-atom) in liquid ammonia (1.5 liter). Ammonium chloride... [Pg.52]

Lithium borohydride, 62 Lithium f-butoxide, 69 Lithium cyanohydridoborate, 92 Lithium diisopropylamide, 477 Lithium reductive deacetoxylation, 56 Lithium reduction of 17a-ethynyl-19-nortestosterone, 55... [Pg.262]

Metal ammonia reduction of 17a-ethynyl-19-nortestosterone, 52 Metal ammonia reductions and reductive alkylations, 43 Methanol-OD, 212... [Pg.262]

To a solution of 1 g of the mixture of 3-ketal-isomers of compound (II) in 10 cc of acetic anhydride is added a solution of 700 mg of p-toluenesulfonic acid in 7 cc of acetic anhydride. The reaction mixture is kept at room temperature and under stirring for 5 hours. After some time a crystalline product begins to precipitate and the precipitation is complete by diluting with water. The precipitate is filtered and crystallized from methanol to give 17a-ethynyl-19-nortestosterone 3,17-diacetate (III), melting point 175°C to 178°C. [Pg.2944]

A solution of 1 g of the diacetate (III) in 100 cc of n-heptane containing 2.5 cc of cyclopentanol and 50 mg of p-toluenesulfonic acid is heated under reflux for 20 hours. After cooling, a few drops of pyridine are added and the solvent is eliminated by evaporation under vacuum. The residue is taken up with methanol to give 3-cyclopentyl enolether of 17a-ethynyl-19-nortestosterone acetate which, after recrystallization from methanol, melts at 182°C to 184°C. [Pg.2944]

Norsteroids are microbially hydroxylated at the la-position, e.g., in the case of 17a-ethynyl-19-nortestosterone with Acremonium strictum71 or Mucor spinosus72-73, and of 17a-ethynyl-17/5-hydroxy-18a-homoestra-4,15-dien-3-one (gestoden, 3) with Aspergillus rfuvatus. ... [Pg.370]

B. mulorum was also the culture of choice in the case of 1 /(-hydroxylation of 17a-ethynyl-19-nortestosterone and 17oc-ethynyl-18a-homo-19-nortestosterone (5)S0 81. [Pg.371]

Norethindrone (17a-ethynyl-19-nortestosterone) (Table 1) also exhibits properties of a suicide inhibitor of human placental aromatase. It is, however, a very weak inhibitor compared to PED d37... [Pg.761]

The total synthesis of the highly progestationally active 6,6-difluoro-18-homo-17a-ethynyl-19-nortestosterone (85) has been reported. The approach of the Russian school was used/ appropriately modified in order to introduce the 18-ethyl group. The gern-difluoro-moiety was prepared from the 5a-fluoro-6-ketone (84) by a procedure described previously. [Pg.424]

The preparation of 17a-ethynyl-l 0/1,17/ -dihydroxyestr-4-en-3-one (5) was achieved by transformation of 17a-ethynylestradiol-17/f (3) with the fungus Aspergillus flavus190-191 17 a-ethynyl-19-nortestosterone (norethisterone, 4) was observed as an intermediate. [Pg.391]

XV 19-Nor-3-(3-oxo-17 -OH-4-androsten-17a-yl)-propionic 7-lactone XVI 17a-Vinyl-19-nortestosterone XVII 17a-Ethynyl-21 -methy Itestosterone XVIII 17a-Ethynyl-21-ethyltesto8terone XIX 17a-Methylestra-5(10) -eneolone... [Pg.312]

Chemical Name 13-ethyl-17-hydroxy-1B,19-dinor-17a-pregn-4-en-20-yn-3-one Common Name 17a-ethynyl-1B-homo-19-nortestosterone... [Pg.1100]

Common Name 17a-Ethynyl-18-homo-19-nortestosterone Structural Formula ... [Pg.2479]

Nitrogen retention evaluation [251] was as good with ]7a-ethylnor-testosterone as with testosterone propionate (subcutaneous administration) or 17a-methyltestosterone (oral administration) [250]. The calcium and phosphorus retention was also favorably affected but as a side effect, mild cholestatic jaundice was observed [256]. Also a marked increase in bromsulfalein retention was observed in humans by administration of 17a-ethylnortestosterone [257]. Other 17o -alkyl substitutions (propyl, allyl, methallyl, ethynyl) caused a decrease of the anabolic activity. A new type of derivatives of 19-nortestosterone was prepared by etherification of the 17/3-hydroxy group [12,143,258]. Among these compounds, 19-nortestosterone-17-(cyclopent-l -enyl) ether (N-81) possesses a favorable anabolic-androgenic ratio without the undesirable side effects. [Pg.93]

Others. The 19-nortestosterone analogs, which instead of the d -3-ketone system contain the A -3-ketone system (unconjugated ketone) showed very similar androgenic and anabolic potencies compared to the A -3-ketone compounds [68]. It is most likely that the A -3-ketone compounds, 17a-ethynyl-17)3-hydroxy-19-norandrost-5-en-3-one (N-37), 17o -ethyl-17 -hydroxy-19-norandrost-5-en-3-one (N-38), and Ha-methyl-17/3-hydroxy-19-norandrost-5-en-3-one (N-39) under the influence of the acid pH of the stomach are rearranged to the A -3-ketones. [Pg.93]

A once-a-month oral contraceptive may be well suited for underdeveloped countries where medical supervision is limited. Norgestrel (17a-ethynyl-18-methyl-19-nortestosterone), in combination with ethynyl estradiol showed good contraceptive efficacy given 21 days in a cycle. The lower dally doses of... [Pg.192]

See other pages where 17a-Ethynyl-19-nortestosterone is mentioned: [Pg.53]    [Pg.35]    [Pg.298]    [Pg.272]    [Pg.343]    [Pg.275]    [Pg.1058]    [Pg.1535]    [Pg.750]    [Pg.1535]    [Pg.53]    [Pg.35]    [Pg.298]    [Pg.272]    [Pg.343]    [Pg.275]    [Pg.1058]    [Pg.1535]    [Pg.750]    [Pg.1535]    [Pg.78]    [Pg.310]    [Pg.274]    [Pg.2480]    [Pg.71]    [Pg.94]    [Pg.355]    [Pg.748]    [Pg.1535]    [Pg.561]   
See also in sourсe #XX -- [ Pg.312 ]



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17-Ethynyl-19-nortestosterone

19- Nortestosterones

19-Nortestosterone

Ethynylation

Ethynyls

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