Claims
- 1. A compound having the formula ##STR23## a pharmaceutically acceptable acid addition salt thereof or a stereochemically isomeric form thereof, wherein
- n is 0 or 1;
- R.sup.1 is hydrogen, nitro, amino, mono- or di(C.sub.1-6 alkyl)amino, halo, C.sub.1-6 alkyl, hydroxy or C.sub.1-6 alkyloxy;
- R.sup.2 is hydrogen; C.sub.1-10 alkyl; C.sub.3-6 alkenyl; C.sub.3-6 alkynyl; C.sub.3-7 cycloalkyl; bicyclo[2.2.1]heptan-2-yl; 2,3-dihydro-1H-indenyl; 1,2,3,4-tetrahydronaphthalenyl; phenyl; substituted phenyl; C.sub.1-10 alkyl substituted with phenyl, substituted phenyl, naphthalenyl, thienyl, furanyl, C.sub.1-4 alkylfuranyl, C.sub.3-7 cycloalkyl, hydroxy or with C.sub.1-6 alkyloxy; or a radical of formula --OR.sup.3 ;
- R.sup.3 is hydrogen; C.sub.1-10 alkyl; C.sub.3-6 alkenyl; phenylC.sub.3-6 alkenyl; C.sub.3-6 alkynyl; pyrimidinyl; diphenylmethyl; 1-C.sub.1-4 alkylpiperidin-4-yl; C.sub.1-10 alkyl substituted with halo, hydroxy, C.sub.1-6 alkyloxy, amino, mono- or di(C.sub.1-6 alkyl)amino, trifluoromethyl, cyano, aminocarbonyl, hydroxycarbonyl, C.sub.1-6 alkyloxycarbonyl, phenyl, substituted phenyl, thienyl, furanyl, C.sub.1-4 alkylfuranyl, pyridinyl, di(C.sub.1-6 alkyl)isoxazolyl, phenoxy, phenylthio, C.sub.3-7 cycloalkyl, 2,3-dihydro-1,4-benzodioxinyl, 1H-benzimidazolyl, C.sub.1-4 alkyl substituted 1H-benzimidazolyl, (1,1'-biphenyl)-4-yl or 2,3-dihydro-2-oxo-1H-benzimidazolyl; and
- each substituted phenyl independently is phenyl substituted with from 1 to 3 substituents independently selected from halo, hydroxy, hydroxymethyl, trifluoromethyl, C.sub.1-6 alkyl, C.sub.1-6 alkyloxy, C.sub.1-6 alkyloxycarbonyl, carboxyl, formyl, (hydroxyimino)methyl, cyano, amino, mono- and di(C.sub.1-6 alkyl)amino and nitro.
- 2. A compound according to claim 1 wherein the 5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl or the 6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5yl moiety is substituted on either the 5 or the 6 position of the benzotriazole moiety.
- 3. A compound according to claim 1 wherein n is 1; R.sup.1 is hydrogen; R.sup.2 is hydrogen, C.sub.1-6 alkyl, C.sub.3-6 alkenyl, C.sub.3-6 alkynyl, C.sub.3-7 cycloalkyl, phenyl, substituted phenyl, bicyclo[2.2.1]heptan-2-yl, 2,3-dihydro-1H-indenyl, 1,2,3,4-tetrahydronaphthalenyl, C.sub.1-6 alkyl substituted with phenyl, substituted phenyl, naphthalenyl, thienyl, furanyl, C.sub.1-4 alkylfuranyl, C.sub.3-7 cycloalkyl, hydroxy, C.sub.1-4 alkyloxy or a radical --OR.sup.3 ; and; R.sup.3 is hydrogen, C.sub.1-6 alkyl, C.sub.3-6 alkenyl, phenylC.sub.3-6 alkenyl; C.sub.3-6 alkynyl; pyrimidinyl; diphenylmethyl, (1-C.sub.1-4 alkyl-4piperidinyl); C.sub.1-6 alkyl substituted with halo, hydroxy, amino, mono- or di(C.sub.1-6 alkyl)amino, trifluoromethyl, cyano, aminocarbonyl, hydroxycarbonyl, C.sub.1-6 alkyloxycarbonyl, phenyl, substituted phenyl, thienyl, furanyl, C.sub.1-4 alkylfuranyl, pyridinyl, di(C.sub.1-6 alkyl)isoxazolyl, phenoxy, phenylthio, C.sub.3-7 cycloalkyl, 2,3-dihydro-1,4-benzodioxinyl, 1H-benzimidazolyl, C.sub.1-4 alkyl substituted 1H-benzimidazolyl, (1,1'-biphenyl)-4-yl or 2,3-dihydro-2-oxo-1H-benzimidazolyl.
- 4. A compound according to claim 1 wherein n is 0; R.sup.1 is hydrogen; R.sup.2 is hydrogen, C.sub.1-6 alkyl, C.sub.3-7 cycloalkyl, C.sub.1-6 alkyl substituted with C.sub.3-7 cycloalkyl or a radical --OR.sup.3 ; R.sup.3 is hydrogen or C.sub.1-6 alkyl.
- 5. A compound according to claim 3 wherein R.sup.2 is C.sub.1-6 alkyl optionally substituted with C.sub.3-7 cycloalkyl; C.sub.3-7 cycloalkyl; bicyclo[2.2.1]heptan-2-yl; 2,3-dihydro-1H-indenyl; 1,2,3,4-tetrahydronaphthalenyl; or a radical --OR.sup.3 ; and
- R.sup.3 is C.sub.1-6 alkyl optionally substituted with hydroxy, cyano, phenyl, substituted phenyl, C.sub.3-7 cycloalkyl; or C.sub.3-6 alkenyl.
- 6. A compound according to claim 5 wherein R.sup.2 is C.sub.1-4 alkyl.
- 7. A compound according to claim 6 wherein the compound is 1-ethyl-6-(5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl)-1H-benzotriazole monohydrochloride.
- 8. A pharmaceutical composition comprising an inert carrier and as active ingredient an estrogen hormone biosynthesis inhibiting amount of a compound as claimed in any one of claims 1-7.
- 9. A method of treating mammals suffering from estrogen dependent disorders, said method comprising the systemic administration to said mammals of an effective amount to treat estrogen dependent disorders of a compound as claimed in any one of claims 1-7.
CROSS-REFERENCE TO RELATED APPLICATION
This is a continuation-in-part of our copending application Ser. No. 430,030 filed Nov. 1, 1989now abandoned.
US Referenced Citations (2)
Number |
Name |
Date |
Kind |
4617307 |
Browne |
Oct 1986 |
|
4755526 |
Hirsch et al. |
Jul 1988 |
|
Foreign Referenced Citations (1)
Number |
Date |
Country |
EP-A-0 293978 |
Dec 1988 |
EPX |
Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
430030 |
Nov 1989 |
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