Patent
17.beta.-substituted 4-azaandrostane derivatives, pharmaceutical compositions containing them and process for preparing same
| العنوان: | 17.beta.-substituted 4-azaandrostane derivatives, pharmaceutical compositions containing them and process for preparing same |
|---|---|
| Patent Number: | 5,583,138 |
| تاريخ النشر: | December 10, 1996 |
| Appl. No: | 08/406,920 |
| Application Filed: | March 23, 1995 |
| مستخلص: | The invention relates to novel 17.beta.-substituted 4-azaandrostane derivatives of general formula (I), ##STR1## wherein R means hydrogen or a C.sub.1-3 alkyl group; R.sup.1 and R.sup.2 are the same or different and stand for hydrogen or a C.sub.1-4 alkyl group with the proviso that both can mean hydrogen only in the case when n is higher than 5; or R.sup.1 and R.sup.2 together means an .alpha.,.omega.-alkylene group containing 5 to 7 carbon atoms, the terminal carbon atoms of said alkylene group being bound to the same ring carbon atom; n is 4, 5, 6 or 7; and bond line represents a single or double bond. Furthermore, the invention relates to pharmaceutical composition containing these compounds as well as a process for the preparation of the compounds of general formula (I). The compounds of general formula (I) exert a 5.alpha.-reductase enzyme-inhibiting effect and therefore, they are useful for treating all diseases, where the aim is to reduce the tissue dihydrotestosterone level, such as the benign prostatic hyperplasia, acne, seborrhoea, female hirsutism or androgenic alopecia. |
| Inventors: | Tuba, Zolt an (Budapest, HUX); Horv ath, Judit (Budapest, HUX); Koll ar, L aszl o (Veszpr em, HUX); Lovas n ee Marsai, M aria (Budapest, HUX); Balogh, G abor (Budapest, HUX); Csehi, Attila (G od, HUX); J avor, Andr as (Budapest, HUX); Hajo os, Gy orgy (Budapest, HUX); Szporny, L aszl o (Budapest, HUX) |
| Assignees: | Richter Gedeon Vegyeszeti Gyar Rt. (Budapest, HUX) |
| Claim: | What is claimed is |
| Claim: | 1. A compound of the Formula (I) ##STR5## wherein R is hydrogen; |
| Claim: | R.sup.1 and R.sup.2 are each methyl or one of R.sup.1 or R.sup.2 is hydrogen and the other is methyl; and |
| Claim: | n is 4 or 5. |
| Claim: | 2. The compound of the Formula (I) defined in claim 1 selected from the group consisting of |
| Claim: | 17beta-(4-methylpiperidinocarbonyl)-3-oxo-4-aza-5alpha-androst-1-ene; |
| Claim: | 17beta-(3,3-dimethylpiperidinocarbonyl)-3-oxo-4-aza-5alpha-androst-1-ene; and |
| Claim: | 17-beta-(2,6-dimethylpiperidinocarbonyl)-3-oxo-4-aza-5alpha-androst-1-ene. |
| Claim: | 3. The compound of the Formula (I) defined in claim 1 which is 17beta-(4-methylpiperidinocarbonyl)-3-oxo-4-aza-5alpha-androst-1-ene. |
| Claim: | 4. A pharmaceutical composition with 5 alpha reductase enzyme inhibiting effect which comprises as active ingredient effective amount of a compound of the Formula (I) as defined in claim 1 in admixture with a pharmaceutically acceptable inert carrier. |
| Claim: | 5. A method for treating acne in a mammalian subject which comprises the step of administering to said subject an anti-acne effective amount of a compound of the Formula (I) as defined in claim 1. |
| Current U.S. Class: | 514/284; 514/183; 514/212; 540/597; 540/481; 546/77 |
| Current International Class: | A61K 3158 |
| Patent References Cited: | 4220775 February 1980 Rasmussen et al. 4377584 March 1983 Rasmussan et al. 4885289 December 1989 Breuer 5304562 April 1994 Biogaz 5312984 May 1994 Nicholas 5410040 April 1995 Tuba et al. 5418238 May 1995 Panzeri |
| Other References: | Stinson, Chem & Eng News 29 Jun. 1992 pp. 7-8. Hellikeer, Wall St. Jour. 7 Jun. 1991 pp. A1, A7. Diani et al. Jour. Clin. Endo. & Metab., vol. 74, pp. 345-350 (1992). Frye, et al. J. Med Chem vol. 36 pp. 4313-4315 (1993). Kuttenn et al. J. Endocr. (1977), vol. 75, 83 to 91. Sansong et al. J. Invest. Dermatol, vol. 56, 366-372, (1971). Siiteri et al. J. Clin. Invest., vol. 49, 1737-1745, (1970). Rittmaster Clin. In. Dermatol, vol. 6, 122-128, (1988). Liang et al. J. Steroid Biochem., vol. 19, 385-390 (1983). Rasmusson, Jour. Med. Chem. vol. 29 pp. 2298-2315 (1986). Back, J. Org. Chem., 1981, 46, 1442 to 1446. Rasmusson J. Med. Chem., 1984, 27, 1690 to 1701. Solomons J. Pharm. Sci., 63, 1974, 19 to 23. Battacharya Synthetic Communications, 30(17), 2683 to 2690 (1990). Brooks Steroids 47/1, Jan. 1986, 1 to 19. Winslow, Wall St. Jour., May 7, 1996 p. B4. |
| Primary Examiner: | Daus, Donald G. |
| Attorney, Agent or Firm: | Dubno, Herbert Myers, Jonathan |
| رقم الانضمام: | edspgr.05583138 |
| قاعدة البيانات: | USPTO Patent Grants |
| الوصف غير متاح. |