Synthesis and biological activity of a new progestogen, 16-methylene- 17α-hydroxy-18-methyl-19-norpregn-4-ene-3,20-dione acetate

Steroids

Volumn 65, Issue 5, 2000, Pages 266-274

  Tuba, Zoltán ^a   Bardin, C Wayne ^b   Dancsi, Anna ^a   Francsics Czinege, Erzsébet ^a   Molnár, Csaba ^a   Csörgei, János ^a   Falkay, George ^c   Koide, Samuel S ^d   Kumar, Narender ^d   Sundaram, Kalyan ^d   Dukát Abrók, Vilma ^a   Balogh, Gábor ^a  

^a GEDEON RICHTER LTD   (Hungary)

^b Thyreos Corporation   (United States)

^c UNIVERSITY OF SZEGED   (Hungary)

^d POPULATION COUNCIL   (United States)

Author keywords

16 methylene 17 hydroxy 18 methyl 19 norpregn 4 ene 3; 20 dione acetate; Clauberg assay; Nestorone; Progestin; Synthesis

Indexed keywords

16 METHYLENE 17ALPHA HYDROXY 18 METHYL 19 NORPREGN 4 ENE 3,20 DIONE ACETATE; CONTRACEPTIVE AGENT; CORN OIL; ELCOMETRINE; ESTRONE; GESTAGEN; LEVONORGESTREL; NANDROLONE DERIVATIVE; PROGESTERONE DERIVATIVE; PROGESTERONE RECEPTOR; PROMEGESTONE; TRITIUM; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; BINDING AFFINITY; CHEMICAL STRUCTURE; CONTRACEPTION; CONTROLLED STUDY; FEMALE; HORMONAL CONTRACEPTION; HORMONE RECEPTOR INTERACTION; NONHUMAN; RAT; SYNTHESIS;

ANIMALS; BIOLOGICAL ASSAY; CONTRACEPTIVE AGENTS, FEMALE; DOSE-RESPONSE RELATIONSHIP, DRUG; ENDOMETRIUM; FEMALE; LEVONORGESTREL; MALE; NORPROGESTERONES; PREGNANCY; PREGNANCY MAINTENANCE; PROGESTERONE; PROGESTERONE CONGENERS; RABBITS; RATS; RATS, SPRAGUE-DAWLEY;

ANIMALIA; ORYCTOLAGUS CUNICULUS; TRITIUM; ZEA MAYS;

EID: 0034037316     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0039-128X(99)00109-9     Document Type: Article

References (33)

1. McClamrock H.D., Adashi E.Y. Pharmacokinetics of desogestrel. J Am Obstet Gynecol. 168:1993;1023-1028.
2. Robinson G.E. Low-dose combined oral contraceptives. Brit J Obst Gynec. 101:1994;1036-1041.
3. Fotherby K. Desogestrel and gestodene in oral contraception a review of European experience . J Drug Dev. 4:1991;101-111.
4. Goldzieher J.W. Lack of androgenicity of 17-hydroxyprogesterone or its 17-caproate ester. J Clin Endocrinol Metab. 17:1957;323-328.
5. Bazin B., Thevenot R., Bursaux C., Paris J. Effect of Nomegestrol acetate, a new progesterone derivative, on pituitary-ovarian function in women. Brit J Obst Gynecol. 94:1987;1199-1204.
6. Lahteenmaki P.L.A. Intestinal absorption of ST-1435 in rat. Contraception. 30:1984;143-145.
7. Shapiro E.L., Legatt T., Weber L., et al. 16-alkylated progestogens. J Med Pharm Chem. 5:1962;975-979.
8. Shapiro E.L., Weber L., Harris H., Miskovitz C., Neri R., Herzog H.L. Synthesis and biological activity of 17-esters of 6-dehydro-16-methylene-17α-hydroxyprogesterones. J Med Chem. 15:1972;716-720.
9. Laurikka-Routti M., Haukkamaa M., Lahteenmaki P. Suppression of the ovarian function with the transdermally given synthetic progestin ST-1435. Fertil Steril. 58:1992;680-684.
10. Alvarez-Sanchez F., Brache V., Jankanitz T., Faunders A. Evaluation of four different contraceptive vaginal rings steroid serum levels, luteal activity, bleeding control, and lipid profiles . Contraception. 46:1992;387-398.
11. Sitruk-Ware R. Transdermal application of steroid hormones for contraception. J Steroid Biochem Molec Biol. 53:1995;247-251.
12. Brower K.R., Douglas I.B. Methylsulfur trichloride. J Am Chem Soc. 73:1951;5787-5789.
13. Mernhof W., Irmscher K., Erb R., Pohl L. Synthesewege zum 17α-hydroxy-16-methylen-19-nor-progesteron und seinem derivativen. Chem Ber. 102:1969;643-658.
14. Beal PF, Lincoln FH, Hogg JA. Abstracts, 132nd National Meeting of the American Chemical Society. New York, NY, 1957. p. 12.
15. Goldberg M.W., Aeschbacher R., Hardegger E. 17α-Oxy-20-keto-Verbindungen der Pregnen- und der Allo-pregnan Reihe. Helv Chim Acta. 26:1943;680-686.
16. Bickart P., Carson F., Jacobus J., Miller G., Mislow K. The thermal racemisation of allylic sulfoxides and the interconversion of allylic sulfoxides and sulfenates. Mechanism and stereochemistry. J Am Chem Soc. 90:1968;4869-4876.
17. Tang R., Mislow K. Rates and equilibria in the interconversion of allylic sulfoxides and sulfenates. J Am Chem Soc. 92:1970;2100-2104.
18. Evans D.A., Andrew G.C., Sims C.L. Reversible 1,3 transposition of sulfoxide and alcohol functions. Potential synthetic utility. J Am Chem Soc. 93:1971;1956-1957.
19. Evans D.A., Andrew G.C. Nucleophilic cleavage of allylic sulfenate esters. Mechanistic observations. J Am Chem Soc. 94:1972;3672-3674.
20. Miller J., Kurz W., Untch K., Stork G. Highly stereoselective total synthesis of prostaglandins via stereospecific sulfenate-sulfoxide transformation 13-cis-15β-prostaglandins E1 to prostaglandins E1. J Am Chem Soc. 96:1974;6774-6778.
21. Li F., Kumar N., Tsong Y.Y., Monder C., Bardin C.W. Synthesis and progestational activity of 16-methylene-17α-hydroxy-19-norpregn-4-ene-3,20-dione and its derivatives. Steroids. 62:1997;403-408.
22. Phillips A., Hahn D.W., Klimek S., McGuire J.L. A comparison of the potencies and activities of progestogens used in contraceptives. Contraception. 36:1987;181-192.
23. McPhail M.K. The assay of progestin. J Physiol. 83:1934;141.
24. Stucki J.C. Maintenance of pregnancy in ovariectomized rats with some newer progestins. Proc Soc Exp Biol Med. 99:1958;500-504.
25. Fujii K. Maintenance of pregnancy by progestins. J Fertil. 6:1961;15-20.
26. Coutinho E.M., da Silva A.R., Kraft H.G. Fertility control with subdermal silastic capsules containing new progestin (ST 1435). Int J Fertil. 2:1976;103-108.
27. Warren M.P., Shantha S. Uses of progesterone in clinical practice. Int J Fertil Women's Med. 44:1999;96-103.
28. Silfverstolbe G., Gustafon A., Samsoie G., Suanborg A. Lipid metabolic studies in oophorectomized women effects of three different progestagens . Acta Obstet Gynecol Scand. 88:1979;89-95.
29. Sundaram K, Kumar N, Tsong YY, Koide SS. Nestorone® a progestin with a unique pharmacological profile. Progesterone, Progestins and Antiprogestins in the Next millenium Congress, Jerusalem, Israel. August 31-September 3, 1999.
30. Collins D. Selectivity information on desogestrel. Am J Obstet Gynecol. 168:1993;1010-1016.
31. Dellettre' J. Mornon JP, Lepicard G, Ojasoo T. Raynaud JP. Steroid flexibility and receptor specificity. J Steroid Biochem. 13:1979;45-59.
32. Kloosterboer H.J., Vonk-Noordegraaf C.A., Turpiln E.W. Selectivity in progesterone and androgen receptor binding of progestagens used in oral contraceptives. Contraception. 38:1988;325-332.
33. Boltela J., Porthe-Nibelle J., Paris J., Lalhou B. Interaction of new 19-norprogesterone derivatives with progestagen, mineralocorticoid and glucocorticoid receptors. J Pharmacol (Paris). 17:1986;699-706.