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Claims for Patent: 3,959,322

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Claims for Patent: 3,959,322

Title: Synthesis of 13-alkyl-gon-4-ones
Abstract:The preparation of 13-methylgon-4-enes and novel 13-polycarbonalkylgon-4-enes by a new total synthesis is described. 13-Alkylgon-4-enes having progestational, anabolic and androgenic activities are prepared by forming a tetracylic gonane structure unsaturated in the 1,3,5(10),9(11) and 14-positions, selectively reducing in the B- and C-rings, and converting the aromatic A-ring compounds so-produced to gon-4-enes by Birch reduction and hydrolysis.
Inventor(s): Hughes; Gordon Alan (Wayne, PA), Smith; Herchel (Wayne, PA)
Assignee: Smith; Herchel (Bryn Mawr, PA)
Application Number:04/388,820
Patent Claims: 1. A chemical compound having a gon-4-ene nucleus, said nucleus having attached thereto, in the 13-position, a polycarbon-alkyl radical having 2 to about 16 carbon atoms; said compound containing at least 19 and up to a maximum of 40 carbon atoms in its carbon-carbon skeleton.

2. A compound of claim 1 which is a 13-polycarbon-alkyl-17-alkyl-17.beta.-hydroxygon-4-en-3-one.

3. A compound of claim 1 which is 13.beta., 17.alpha.-diethyl-17.beta.-hydroxygon-4-en-3-one.

4. A compound of claim 1 which is a 13-polycarbon-alkyl-17-alkynyl-17.beta.-hydroxygon-4-en-3-one.

5. A compound of claim 1 which is 13.beta.-ethyl-17.alpha.-ethynyl-17.beta.-hydroxygon-4-en-3-one.

6. A compound of claim 1 which is 13.beta.-ethyl-17.alpha.-chloroethynyl-17.beta.-hydroxygon-4-en-3-one.

7. A compound of claim 1 which is a 13-polycarbon-alkyl-17.beta.-hydroxygon-4-en-3-one-17-ester.

8. A compound of claim 1 which is 13.beta.-ethyl-17.beta.-hydroxygon-4-en-3-one 17-decanoate.

9. A process for preparing a compound having a 17.alpha.-alkyl-17.beta.-hydroxygon-4-en-3-one nucleus substituted in the 13-position by a polycarbon-alkyl radical, comprising: (a) treating a compound having a gona-2,5(10)-dien-17-one nucleus substituted in the 13-position by a monovalent polycarbon-alkyl radical with an alkyl Grignard reagent to obtain as the product a compound having a 17.beta.-alkylgona-2,5(10)-diene-17.alpha.-ol nucleus, and (b) hydrolyzing said product in the presence of a mineral acid.

10. A process for preparing a compound having a 17.alpha.-alkynyl-17.beta.-hydroxygon-4-en-3-one nucleus substituted in the 13-position by a polycarbon-alkyl radical, comprising: (a) treating a compound having a gona-2,5(10)-dien-17-one nucleus substituted in the 13-position by a polycarbon-alkyl radical with an alkali metal acetylide, and (b) hydrolyzing the product with mineral acid.

11. A process for preparing a 4-dehydro-13-alkyl-17-hydroxygonane comprising: (a) converting a compound having a 5-phenylpent-1-yne nucleus, ring unsubstituted in at least one position ortho to the point of chain attachment, to its acetylene amine derivative by means of a Mannich reaction; (b) hydrating the acetylenic linkage to form a 3-keto compound; (c) condensing said 3-keto compound with a 2-alkyl-1,3-dioxocyclopentano compound under Michael reaction conditions; (d) cyclodehydrating the Michael reaction product in the presence of an acid to form a 1,3,5(10),8,14-pentadehydro-13-alkylgonane; (e) selectively saturating the 14(15) double bond of said gonane with hydrogen in the presence of a catalyst to obtain a 1,3,5(10),8-tetradehydro-13-alkylgonane, (f) partially reducing the A-ring and reducing the 17-oxo group to 17-hydroxy under Birch reduction conditions; and (h) hydrolyzing the product with mineral acid.

12. A compound of the formula ##SPC1##

where R represents a polycarbon lower alkyl group.

13. A compound of the formula ##SPC2##

wherein R is selected from the group consisting of hydrogen and lower alkanoyl.

14. A compound of the formula ##SPC3##

15. A compound of claim 1 which is 13.beta.-ethyl-17.beta.-acetylgon-4-en-3-one.

16. A compound of claim 1 which is 13.beta.-ethyl-17-ethynylgon-4-en-17.beta.-ol.

17. A compound of claim 1 which is 13.beta.-ethyl-17.alpha.-ethynyl-17.beta.-hydroxygon-4-en-3-one, 2'-tetrahydropyranyl ether.

18. A compound of claim 1 which is 13.beta.-ethyl-17.alpha.-chloroethynyl-17.beta.-hydroxygon-4-en-3-one, 2'-tetrahydropyranyl ether.

19. A compound of claim 1 which is 13.beta.-ethyl-17.alpha.-ethynyl-17.beta.-hydroxygon-4-en-3-one, acetate.

20. A compound of claim 1 which is 13.beta.-ethyl-17.alpha.-chloroethynyl-17-hydroxygon-4-en-3-one, acetate.

21. A compound of claim 1 which is 17-chloroethynyl-13.beta.-ethylgon-4-ene-3,17.beta.-diol, 3-acetate.

22. A compound of claim 1 which is 13.beta.-ethyl-17.alpha.-ethynylgon-4-en-3,17.beta.-diol, 3-acetate.

23. A compound of claim 1 which is 3(13-ethyl-17.beta.-hydroxy-3-oxogon-4-en-17.alpha.-yl)propionic acid, .gamma.-lactone.

24. A compound of claim 4 which is 17.alpha.-chloroethynyl-17-hydroxy-13.beta.-n-propylgon-4-en-3-one.

25. A compound of claim 4 which is 17.alpha.-chloroethynyl-13.beta.-ethyl-17-hydroxygon-4-en-3-one.

26. A compound of claim 4 which is 13.beta.-ethyl-17.alpha.-ethynyl-17-hydroxy-6.alpha.-methylgon-4-en-3-one.

27. A compound of claim 4 which is 13.beta.-n-propyl-17.alpha.-ethynyl-17.beta.-hydroxygon-4-en-3-one.

28. A compound of the formula ##SPC4##

wherin R represents an alkyl radical having from 2 to 16 carbon atoms, and R.sub.1 represents a member selected from the group consisting of hydrogen and the acyl radical of an organic caboxylic acid having from 1 to 18 carbon atoms selected from the group consisting of alkanoic, alkenoic, cycloalkylalkanoic and arylalkanoic acids.

29. A compound selected from the group consisting of 13-polycarbonalkyl-17.alpha.-substituted-17.beta.-hydroxygona-4-en-3-one and 17.beta.-alkanoyl esters thereof, wherein the 17.alpha.-position substituent is a halogenated unsaturated hydrocarbon radical.

30. A compound as defined in claim 29, wherein the halogenared unsaturated hydrocabon radical in the 17.alpha.-position is haloethynyl.

31. A compound as defined in claim 30, wherein the 13-polycarbonalkyl substituent is ethyl.

32. A compound of claim 1 which is a 13.beta.-ethyl-17.alpha.-ethynyl-gon-4-en-3-one-17.beta.-ol or its 17-lower-alkanoate.

33. A compound of claim 1 which is a 13.beta.-ethyl-17.alpha.-ethynyl-gon-4-en-3-one-17.beta.-ol or its 17-acetate.

34. A compound of claim 1 which is a 13.beta.-polycarbonalkyl-17-alkynyl-17.beta.-hydroxygon-4-en-3-one or its 17-lower alkanoate.

35. A compound of claim 1 which is a 13.beta.-ethyl-17-alkynyl-17.beta.-hydroxygon-4-en-3-one or its 17-lower-alkanoate.

36. A compound of claim 1 which is a 13.beta.-ethyl-17-alkynyl-17.beta.-hydroxygon-4-en-3-one or its 17-acetate.

37. A compound of claim 1 which is a 13.beta.-polycarbonalkyl-17-alkynyl-17.beta.-hydroxy steriod or its 17-lower-alkanoate having a gon-4-ene carbon-carbon skeleton.

38. A compound of claim 1 which is a 13.beta.-ethyl-17-alkynyl-17.beta.-hydroxy steroid or its 17-lower-alkanoate having a gon-4-ene carbon-carbon skeleton.

39. A compound of claim 1 which is a 13.beta.-ethyl-17-alkynyl-17.beta.-hydroxy steroid or its 17-acetate having a gon-4-ene carbon-carbon skeleton.

40. A compound of claim 1 which is a 13.beta.-ethyl-17-ethynyl-17.beta.-hydroxy steroid or its 17-acetate having a gon-4-ene carbon-carbon skeleton.

41. A compound of claim 1 which is a 13.beta.-polycarbonalkyl-17.alpha.-alkynyl-17.beta.-hydroxy steroid or its 17-lower-alkanoate, having a gon-4-ene nucleus and a 3-substituent selected from the group consisting of oxo, hydroxy, and a group convertible thereto by hydrolysis.

42. A compound of claim 1 which is a 13.beta.-ethyl-17.alpha.-ethynyl-17.beta.-hydroxy steroid or its 17-lower-alkanoate having a gon-4-ene nucleus and a 3-substituent selected from the group consisting of oxo, hydroxy, and a group convertible thereto by hydrolysis.

43. A compound of claim 1 which is a 13.beta.-ethyl-17.alpha.-ethynyl-17.beta.-hydroxy steroid or its 17-acetate having a gon-4-ene nucleus and a 3-substituent selected from the group consisting of oxo, hydroxy, and a group convertible thereto by hydrolysis.

44. A compound of claim 1 which is a compound of the formula: ##SPC5##

wherein R is selected from the group consisting of oxo, hydroxy, and a group convertible thereto by hydrolysis.

45. A compound of claim 1 wherein the polycarbon alkyl radical in the 13-position is ethyl.

46. A compound of claim 1, having a substituent in the 17-position linked to said 17-position through a carbon bond, thus being a part of said carbon-carbon skeleton, said 17-substituent containing a maximum of 4 carbon atoms.

47. A compound of claim 46 wherein an alpha-ethynyl group is present in the 17-position.

48. A compound of claim 47 wherein an acetoxy or hydroxy group is also present at the 17-position.
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