Methylpyrrolopyrimidinecarboxamides
View Patent ↗The compounds of Formula (I), wherein R1, R2, R21, R22, R23, R24, Y and R3 have the meanings as given in the description, the salts thereof, the stereoisomers of the compounds and the salts thereof are effective inhibitors of the type 5 phosphodiesterase.
1. A compound of formula (I)
wherein
R1 is —CH 2 -3-4C-cycloalkyl,
R2 is hydrogen,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, —C(O)-1-4C-alkyl or 1-4C-fluoroalkyl, or R21 and R22 combine to form a group —O—CH 2 —O—,
R23 is hydrogen, halogen or 1-4C-alkoxy,
R24 is hydrogen,
Y is —(CH 2 ) n —,
n is 0,
R3 is a cyclohexyl or cyclopentyl group substituted by R6 and optionally substituted by R61,
R6 is —NH—C(O)—R7,
R61 is halogen or 1-4C-alkyl,
R7 is 1-4C-alkyl, which is optionally substituted by R71, or R7 is 1-4C-alkoxy,
R71 is 1-4C-alkoxy,
or a salt thereof, a stereoisomer of the compound or a salt of the stereoisomer.
2. A compound of formula (I)
wherein
R1 is —CH 2 -3-4C-cycloalkyl,
R2 is hydrogen,
R21 is hydrogen,
R22 is difluoromethyl or trifluoromethyl,
R23 is hydrogen,
R24 is hydrogen,
Y is —(CH 2 ) n —,
n is 0,
R3 is a cyclohexyl group substituted by R6 and optionally substituted by R61,
R6 is —NH—C(O)—R7,
R61 is fluoro or methyl,
R7 is methyl or ethyl, which are optionally substituted by R71,
R71 is methoxy or hydroxy,
or a salt thereof, a stereoisomer of the compound or a salt of the stereoisomer.
3. A compound of formula I according to claim 2 , wherein
R1 is —CH 2 -3-4C-cycloalkyl,
R2 is hydrogen,
R21 is hydrogen,
R22 is difluoromethyl,
R23 is hydrogen,
R24 is hydrogen,
Y is —(CH 2 ) n —,
n is 0,
R3 is a cyclohexyl group substituted by R6 and optionally substituted by R61,
R6 is —NH—C(O)—R7,
R61 is fluoro or methyl,
R7 is methyl or ethyl, which are optionally substituted by R71,
R71 is methoxy or hydroxy,
or a salt thereof, a stereoisomer of the compound or a salt of the stereoisomer.
4. A compound according to claim 1 selected from the group consisting of N-(trans-4-acetamidocyclohexyl)-4-[5-(cyclopropylmethoxy)-1,3-benzodioxol-4-yl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[5-(Cyclopropylmethoxy)-1,3-benzodioxol-4-yl]-6-methyl-N-[trans-4-(propionylamino)cyclohexyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[5-(Cyclopropylmethoxy)-1,3-benzodioxol-4-yl]-N-{trans-4-[(methoxyacetyl)amino]cyclohexyl}-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; Ethyl {trans-4-[({4-[5-(cyclopropylmethoxy)-1,3-benzodioxol-4-yl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidin-7-yl}carbonyl)amino]cyclohexyl}carbamate; N-(cis-4-acetamidocyclohexyl)-4-[5-(cyclopropylmethoxy)-1,3-benzodioxol-4-yl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[5-(Cyclopropylmethoxy)-1,3-benzodioxol-4-yl]-6-methyl-N-[cis-4-(propionylamino)cyclohexyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[5-(Cyclopropylmethoxy)-1,3-benzodioxol-4-yl]-N-{cis-4-[(methoxyacetyl)amino]cyclohexyl}-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; Ethyl {cis-4-[({4-[5-(cyclopropylmethoxy)-1,3-benzodioxol-4-yl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidin-7-yl}carbonyl)amino]cyclohexyl}carbamate; N-(trans-4-acetamidocyclohexyl)-4-[2-(cyclopropylmethoxy)-4-fluorophenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-4-fluorophenyl]-6-methyl-N-[trans-4-(propionylamino)cyclohexyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-4-fluorophenyl]-N-{trans-4-[(methoxyacetyl)amino]cyclohexyl}-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; N-(cis-4-acetamidocyclohexyl)-4-[2-(cyclopropylmethoxy)-4-fluorophenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-4-fluorophenyl]-6-methyl-N-[cis-4-(propionylamino)cyclohexyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-4-fluorophenyl]-N-{cis-4-[(methoxyacetyl)amino]cyclohexyl}-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; N-(trans-4-acetamidocyclohexyl)-4-[2-(cyclopropylmethoxy)-5-fluorophenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-5-fluorophenyl]-6-methyl-N-[trans-4-(propionylamino)cyclohexyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-5-fluorophenyl]-N-{trans-4-[(methoxyacetyl)amino]cyclohexyl}-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; Ethyl {trans-4-[({4-[2-(cyclopropylmethoxy)-5-fluorophenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidin-7-yl}carbonyl)amino]cyclohexyl}carbamate; N-(cis-4-acetamidocyclohexyl)-4-[2-(cyclopropylmethoxy)-5-fluorophenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; N-(trans-4-acetamidocyclohexyl)-4-[2-(cyclopropylmethoxy)-4-methoxyphenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; N-(cis-4-acetamidocyclohexyl)-4-[2-(cyclopropylmethoxy)-4-methoxyphenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; N-(trans-4-acetamidocyclohexyl)-4-[2-(cyclopropylmethoxy)-5-methoxyphenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-5-methoxyphenyl]-6-methyl-N-[trans-4-(propionylamino)cyclohexyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-5-methoxyphenyl]-N-{trans-4-[(methoxyacetyl)amino]cyclohexyl}-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; N-(cis-4-acetamidocyclohexyl)-4-[2-(cyclopropylmethoxy)-5-methoxyphenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-5-methoxyphenyl]-6-methyl-N-[cis-4-(propionylamino)cyclohexyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-5-methoxyphenyl]-N-{cis-4-[(methoxyacetyl)amino]cyclohexyl}-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; N-[trans-4-(acetylamino)cyclohexyl]-4-[2-(cyclopropylmethoxy)-5-methylphenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-5-methylphenyl]-6-methyl-N-[trans-4-(propanoylamino)cyclohexyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-5-methylphenyl]-N-{trans-4-[(methoxyacetyl)amino]cyclohexyl}-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; N-[cis-4-(acetylamino)cyclohexyl]-4-[2-(cyclopropylmethoxy)-5-methylphenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-5-methylphenyl]-6-methyl-N-[cis-4-(propanoylamino)cyclohexyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-5-methylphenyl]-N-{cis-4-[(methoxyacetyl)amino]cyclohexyl}-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; N-[trans-4-(acetylamino)cyclohexyl]-4-[2-(cyclopropylmethoxy)-5-(trifluoromethyl)phenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(cyclopropylmethoxy)-5-(trifluoromethyl)phenyl]-6-methyl-N-[trans-4-(propanoylamino)cyclohexyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-5-(trifluoromethyl)phenyl]-N-{trans-4-[(methoxyacetyl)amino]cyclohexyl}-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; N-[cis-4-(acetylamino)cyclohexyl]-4-[2-(cyclopropylmethoxy)-5-(trifluoromethyl)phenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-5-(trifluoromethyl)phenyl]-6-methyl-N-[cis-4-(propanoylamino)cyclohexyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-5-(trifluoromethyl)phenyl]-N-{cis-4-[(methoxyacetyl)amino]cyclohexyl}-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; N-(trans-4-Acetamidocyclohexyl)-4-[2-(cyclopropylmethoxy)-4-fluoro-5-methoxyphenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-4-fluoro-5-methoxyphenyl]-6-methyl-N-[trans-4-(propionylamino)cyclohexyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-4-fluoro-5-methoxyphenyl]-N-{trans-4-[(methoxyacetyl)amino]cyclohexyl}-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; Ethyl {trans-4-[({4-[2-(cyclopropylmethoxy)-4-fluoro-5-methoxyphenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidin-7-yl}carbonyl)amino]cyclohexyl}carbamate; N-(cis-4-Acetamidocyclohexyl)-4-[2-(cyclopropylmethoxy)-4-fluoro-5-methoxyphenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-4-fluoro-5-methoxyphenyl]-6-methyl-N-[cis-4-(propionylamino)cyclohexyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-4-fluoro-5-methoxyphenyl]-N-{cis-4-[(methoxyacetyl)amino]cyclohexyl}-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; N-[trans-4-(Acetylamino)cyclohexyl]-4-[2-(cyclopropylmethoxy)-4-fluoro-5-methylphenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-4-fluoro-5-methylphenyl]-6-methyl-N-[trans-4-(propanoylamino)cyclohexyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-4-fluoro-5-methylphenyl]-N-{trans-4-[(methoxyacetyl)amino]cyclohexyl}-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; N-[cis-4-(Acetylamino)cyclohexyl]-4-[2-(cyclopropylmethoxy)-4-fluoro-5-methylphenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-4-fluoro-5-methylphenyl]-6-methyl-N-[cis-4-(propanoylamino)cyclohexyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-4-fluoro-5-methylphenyl]-N-{cis-4-[(methoxyacetyl)amino]cyclohexyl}-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; N-(trans-4-Acetamidocyclohexyl)-4-[2-(cyclopropylmethoxy)-5-fluoro-4-methoxyphenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-5-fluoro-4-methoxyphenyl]-6-methyl-N-[trans-4-(propionylamino)cyclohexyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-5-fluoro-4-methoxyphenyl]-N-{trans-4-[(methoxyacetyl)amino]cyclohexyl}-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; N-(cis-4-Acetamidocyclohexyl)-4-[2-(cyclopropylmethoxy)-5-fluoro-4-methoxyphenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-5-fluoro-4-methoxyphenyl]-6-methyl-N-[cis-4-(propionylamino)cyclohexyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-5-fluoro-4-methoxyphenyl]-N-{cis-4-[(methoxyacetyl)amino]cyclohexyl}-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; Ethyl {cis-4-[({4-[2-(cyclopropylmethoxy)-5-fluoro-4-methoxyphenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidin-7-yl}carbonyl)amino]cyclohexyl}carbamate; N-[trans-4-(Acetylamino)cyclohexyl]-4-[2-(cyclopropylmethoxy)-5-ethylphenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-5-ethylphenyl]-6-methyl-N-[trans-4-(propanoylamino)cyclohexyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-5-ethylphenyl]-N-{trans-4-[(methoxyacetyl)amino]cyclohexyl}-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; N-[cis-4-(Acetylamino)cyclohexyl]-4-[2-(cyclopropylmethoxy)-5-ethylphenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-5-ethylphenyl]-6-methyl-N-[cis-4-(propanoylamino)cyclohexyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-5-ethylphenyl]-N-{cis-4-[(methoxyacetyl)amino]cyclohexyl}-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; N-[trans-4-(Acetylamino)cyclohexyl]-4-[2-(cyclopropylmethoxy)-5-(propan-2-yl)phenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-5-(propan-2-yl)phenyl]-N-{trans-4-[(methoxyacetyl)amino]cyclohexyl}-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; N-[cis-4-(Acetylamino)cyclohexyl]-4-[2-(cyclopropylmethoxy)-5-(propan-2-yl)phenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-5-(propan-2-yl)phenyl]-N-{cis-4-[(methoxyacetyl)amino]cyclohexyl}-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; N-[trans-4-(Acetylamino)cyclohexyl]-4-[5-acetyl-2-(cyclopropylmethoxy)phenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[5-Acetyl-2-(cyclopropylmethoxy)phenyl]-6-methyl-N-[trans-4-(propanoylamino)cyclohexyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[5-Acetyl-2-(cyclopropylmethoxy)phenyl]-N-{trans-4-[(methoxyacetyl)amino]cyclohexyl}-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; tert-Butyl {trans-4-[({4-[5-(cyclopropylmethoxy)-1,3-benzodioxol-4-yl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidin-7-yl}carbonyl)amino]cyclohexyl}carbamate; tert-Butyl {cis-4-[({4-[5-(cyclopropylmethoxy)-1,3-benzodioxol-4-yl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidin-7-yl}carbonyl)amino]cyclohexyl}carbamate; tert-Butyl {trans-4-[({4-[2-(cyclopropylmethoxy)-4-fluorophenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidin-7-yl}carbonyl)amino]cyclohexyl}carbamate; tert-butyl {cis-4-[({4-[2-(cyclopropylmethoxy)-4-fluorophenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidin-7-yl}carbonyl)amino]cyclohexyl}carbamate; tert-Butyl {trans-4-[({4-[2-(cyclopropylmethoxy)-5-fluorophenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidin-7-yl}carbonyl)amino]cyclohexyl}carbamate; tert-Butyl {cis-4-[({4-[2-(cyclopropylmethoxy)-5-fluorophenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidin-7-yl}carbonyl)amino]cyclohexyl}carbamate; tert-Butyl {trans-4-[({4-[2-(cyclopropylmethoxy)-4-methoxyphenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidin-7-yl}carbonyl)amino]cyclohexyl}carbamate; tert-Butyl {cis-4-[({4-[2-(cyclopropylmethoxy)-4-methoxyphenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidin-7-yl}carbonyl)amino]cyclohexyl}carbamate; tert-Butyl {trans-4-[({4-[2-(cyclopropylmethoxy)-5-methoxyphenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidin-7-yl}carbonyl)amino]cyclohexyl}carbamate; tert-Butyl {cis-4-[({4-[2-(cyclopropylmethoxy)-5-methoxyphenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidin-7-yl}carbonyl)amino]cyclohexyl}carbamate; tert-Butyl {trans-4-[({4-[2-(cyclopropylmethoxy)-5-methylphenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidin-7-yl}carbonyl)amino]cyclohexyl}carbamate; tert-Butyl {cis-4-[({4-[2-(cyclopropylmethoxy)-5-methylphenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidin-7-yl}carbonyl)amino]cyclohexyl}carbamate; tert-Butyl {trans-4-[({4-[2-(cyclopropylmethoxy)-5-(trifluoromethyl)phenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidin-7-yl}carbonyl)amino]cyclohexyl}carbamate; tert-Butyl {cis-4-[({4-[2-(cyclopropylmethoxy)-5-(trifluoromethyl)phenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidin-7-yl}carbonyl)amino]cyclohexyl}carbamate; tert-Butyl {trans-4-[({4-[2-(cyclopropylmethoxy)-4-fluoro-5-methoxyphenyl]-6-methyl-5H-pyrrolo[3,2-c]pyrimidin-7-yl}carbonyl)amino]cyclohexyl}carbamate; tert-Butyl {cis-4-[({4-[2-(cyclopropylmethoxy)-4-fluoro-5-methoxyphenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidin-7-yl}carbonyl)amino]cyclohexyl}carbamate; tert-Butyl {trans-4-[({4-[2-(cyclopropylmethoxy)-4-fluoro-5-methylphenyl]-6-methyl-5H-pyrrolo yl}carbonyl)amino]cyclohexyl}carbamate; tert-Butyl {cis-4-[({4-[2-(cyclopropylmethoxy)-4-fluoro-5-methylphenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidin-7-yl}carbonyl)amino]cyclohexyl}carbamate; tert-Butyl {trans-4-[({4-[2-(cyclopropylmethoxy)-5-fluoro-4-methoxyphenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidin-7-yl}carbonyl)amino]cyclohexyl}carbamate; tert-Butyl {cis-4-[({4-[2-(cyclopropylmethoxy)-5-fluoro-4-methoxyphenyl]-6-methyl-5H-pyrrolo[3,2-d]yl}carbonyl)amino]cyclohexyl}carbamate; tert-Butyl {trans-4-[({4-[2-(cyclopropylmethoxy)-5-ethylphenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidin-7-yl}carbonyl)amino]cyclohexyl}carbamate; tert-butyl {cis-4-[({4-[2-(cyclopropylmethoxy)-5-ethylphenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidin-7-yl}carbonyl)amino]cyclohexyl}carbamate; tert-Butyl {trans-4-[({4-[2-(cyclopropylmethoxy)-5-(propan-2-yl)phenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidin-7-yl}carbonyl)amino]cyclohexyl}carbamate; tert-Butyl {cis-4-[({4-[2-(cyclopropylmethoxy)-5-(propan-2-yl)phenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidin-7-yl}carbonyl)amino]cyclohexyl}carbamate; tert-Butyl {trans-4-[({4-[2-(cyclopropylmethoxy)-5-(2-methyl-1,3-dioxolan-2-yl)phenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidin-7-yl}carbonyl)amino]cyclohexyl}carbamate; N-[trans-4-(Acetylamino)cyclohexyl]-4-[2-(cyclopropylmethoxy)-5-(difluoromethyl)phenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-5-(difluoromethyl)phenyl]-6-methyl-N-[trans-4-(propanoylamino)cyclohexyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-5-(difluoromethyl)phenyl]-N-{trans-4-[(methoxyacetyl)amino]cyclohexyl}-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-5-(difluoromethyl)phenyl]-6-methyl-N-[(1S,3S)-3-(propanoylamino)cyclopentyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-5-(difluoromethyl)phenyl]-N-{(1S,3S)-3-[(methoxyacetyl)amino]cyclopentyl}-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; N-[(1R*,2R*,4R*)-4-(Acetylamino)-2-fluorocyclopentyl]-4-[2-(cyclopropylmethoxy)-5-(difluoromethyl)phenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-5-(difluoromethyl)phenyl]-N-[(1R*,2R*,4R*)-2-fluoro-4-(propanoylamino)cyclopentyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-5-(difluoromethyl)phenyl]-N-{(1R*,2R*,4R*)-2-fluoro-4-[(methoxyacetyl)amino]cyclopentyl}-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; N-[(1S*,2S*,4S*)-4-(Acetylamino)-2-methylcyclohexyl]-4-[2-(cyclopropylmethoxy)-5-(difluoromethyl)phenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-5-(difluoromethyl)phenyl]-6-methyl-N-[(1S*,2S*,4S*)-2-methyl-4-(propanoylamino)cyclohexyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-5-(difluoromethyl)phenyl]-N-{(1S*,2S*,4S*)-4-[(methoxyacetyl)amino]-2-methylcyclohexyl}-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; N-[(1R*,2R*,4R*)-4-(Acetylamino)-2-fluorocyclohexyl]-4-[2-(cyclopropylmethoxy)-5-(difluoromethyl)phenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-5-(difluoromethyl)phenyl]-N-[(1R*,2R*,4R*)-2-fluoro-4-(propanoylamino)cyclohexyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-5-(difluoromethyl)phenyl]-N-{(1R*,2R*,4R*)-2-fluoro-4-[(methoxyacetyl)amino]cyclohexyl}-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; N-[(1S*,3S*,4S*)-4-(Acetylamino)-3-methylcyclohexyl]-4-[2-(cyclopropylmethoxy)-5-(difluoromethyl)phenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-5-(difluoromethyl)phenyl]-6-methyl-N-[(1S*,3S*,4S*)-3-methyl-4-(propanoylamino)cyclohexyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-5-(difluoromethyl)phenyl]-N-{(1S*,3 S*,4S*)-4-[(methoxyacetyl)amino]-3-methylcyclohexyl}-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; N-[(1S*,3S*,4S*)-4-(Acetylamino)-3-fluorocyclohexyl]-4-[2-(cyclopropylmethoxy)-5-(difluoromethyl)phenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-5-(difluoromethyl)phenyl]-N-[(1S*,3S*,4S*)-3-fluoro-4-(propanoylamino)cyclohexyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-5-(difluoromethyl)phenyl]-N-{(1S*,3S*,4S*)-3-fluoro-4-[(methoxyacetyl)amino]cyclohexyl}-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; N-[(1R*,3S*,4S*)-3-(Acetylamino)-4-methylcyclopentyl]-4-[2-(cyclopropylmethoxy)-5-(difluoromethyl)phenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-5-(difluoromethyl)phenyl]-6-methyl-N-[(1R*,3S*,4S*)-3-methyl-4-(propanoylamino)cyclopentyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-5-(difluoromethyl)phenyl]-N-{(1R*,3S*,4S*)-3-[(methoxyacetyl)amino]-4-methylcyclopentyl}-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; N-[(1R*,2R*,4S*)-4-(acetylamino)-2-methylcyclopentyl]-4-[2-(cyclopropylmethoxy)-5-(difluoromethyl)phenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-5-(difluoromethyl)phenyl]-6-methyl-N-[(1R*,2R*,4S*)-2-methyl-4-(propanoylamino)cyclopentyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-5-(difluoromethyl)phenyl]-N-{(1R*,2R*,4S*)-4-[(methoxyacetyl)amino]-2-methylcyclopentyl}-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; N-[(1S*,3S*,4S*)-3-(Acetylamino)-4-fluorocyclopentyl]-4-[2-(cyclopropylmethoxy)-5-(difluoromethyl)phenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-5-(difluoromethyl)phenyl]-N-[(1S*,3S*,4S*)-3-fluoro-4-(propanoylamino)cyclopentyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(cyclopropylmethoxy)-5-(difluoromethyl)phenyl]-N-{(1S*,3S*,4S*)-3-fluoro-4-[(methoxyacetyl)amino]cyclopentyl}-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; N-[(1S*,2R*,4S*)-4-(Acetylamino)-2-fluorocyclohexyl]-4-[2-(cyclopropylmethoxy)-5-(difluoromethyl)phenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-5-(difluoromethyl)phenyl]-N-[(1S*,2R*,4S*)-2-fluoro-4-(propanoylamino)cyclohexyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-5-(difluoromethyl)phenyl]-N-{(1S*,2R*,4S*)-2-fluoro-4-[(methoxyacetyl)amino]cyclohexyl}-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; salts of these compounds, stereoisomers of these compounds, and salts of the stereoisomers of these compounds.
5. A compound according to claim 2 selected from the group consisting of 4-[2-(Cyclopropylmethoxy)-5-(trifluoromethyl)phenyl]-N-{trans-4-[(hydroxyacetyl)amino]cyclohexyl}-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-5-(trifluoromethyl)phenyl]-N-(trans-4-{[(2S)-2-hydroxypropanoyl]amino}cyclohexyl)-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-5-(trifluoromethyl)phenyl]-N-{cis-4-[(hydroxyacetyl)amino]cyclohexyl}-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; 4-[2-(Cyclopropylmethoxy)-5-(trifluoromethyl)phenyl]-N-(cis-4-{[(2S)-2-hydroxypropanoyl]amino}cyclohexyl)-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide; salts of these compounds, stereoisomers of these compounds, and salts of the stereoisomers of these compounds.
6. A compound according to claim 1 selected from the group consisting of 4-[2-(cyclopropylmethoxy)-5-(trifluoromethyl)phenyl]-6-methyl-N-[trans-4-(propanoylamino)cyclohexyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide, a salt thereof, a stereoisomer of the compound and a salt of the stereoisomer.
7. A compound according to claim 1 selected from the group consisting of 4-[2-(Cyclopropylmethoxy)-5-(difluoromethyl)phenyl]-6-methyl-N-[trans-4-(propanoylamino)cyclohexyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide, a salt thereof, a stereoisomer of the compound and a salt of the stereoisomer.
8. A compound according to claim 1 selected from the group consisting of 4-[2-(Cyclopropylmethoxy)-5-(difluoromethyl)phenyl]-N-{trans-4-[(methoxyacetyl)amino]cyclohexyl}-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide, a salt thereof, a stereoisomer of the compound and a salt of the stereoisomer.
9. A compound according to claim 1 selected from the group consisting of 4-[2-(Cyclopropylmethoxy)-5-(difluoromethyl)phenyl]-N-[(1R*,2R*,4R*)-2-fluoro-4-(propanoylamino)cyclohexyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide, a salt thereof, a stereoisomer of the compound and a salt of the stereoisomer.
10. A compound according to claim 1 selected from the group consisting of 4-[2-(Cyclopropylmethoxy)-5-(difluoromethyl)phenyl]-N-{(1R*,2R*,4R*)-2-fluoro-4-[(methoxyacetyl)amino]cyclohexyl}-6-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-carboxamide, a salt thereof, a stereoisomer of the compound and a salt of the stereoisomer.
11. A pharmaceutical composition comprising at least one of the compounds, pharmaceutically acceptable salts thereof, stereoisomers of the compounds, or the pharmaceutically acceptable salts thereof according to claim 1 , together with at least one pharmaceutically acceptable auxiliary.
12. A pharmaceutical composition comprising at least one of the compounds, pharmaceutically acceptable salts thereof, stereoisomers of the compounds or the pharmaceutically acceptable salts thereof according to claim 4 , together with at least one pharmaceutically acceptable auxiliary.
13. A pharmaceutical composition comprising at least one of the compounds, pharmaceutically acceptable salts thereof, stereoisomers of the compounds or the pharmaceutically acceptable salts thereof according to claim 5 , together with at least one pharmaceutically acceptable auxiliary.
14. A pharmaceutical composition comprising at least one of the compounds, pharmaceutically acceptable salts thereof, stereoisomers of the compounds or the pharmaceutically acceptable salts thereof according to claim 6 , together with at least one pharmaceutically acceptable auxiliary.
15. A pharmaceutical composition comprising at least one of the compounds, pharmaceutically acceptable salts thereof, stereoisomers of the compounds or the pharmaceutically acceptable salts thereof according to claim 6 , together with at least one pharmaceutically acceptable auxiliary.
16. A pharmaceutical composition comprising at least one of the compounds, pharmaceutically acceptable salts thereof, stereoisomers of the compounds or the pharmaceutically acceptable salts thereof according to claim 8 , together with at least one pharmaceutically acceptable auxiliary.
17. A pharmaceutical composition comprising at least one of the compounds, pharmaceutically acceptable salts thereof, stereoisomers of the compounds or the pharmaceutically acceptable salts thereof according to claim 9 , together with at least one pharmaceutically acceptable auxiliary.
18. A pharmaceutical composition comprising at least one of the compounds, pharmaceutically acceptable salts thereof, stereoisomers of the compounds or the pharmaceutically acceptable salts thereof according to claim 10 together with at least one pharmaceutically acceptable auxiliary.
19. A method for treating portal hypertension comprising administering to a patient in need thereof a therapeutically effective amount of a compound, a pharmaceutically acceptable salt thereof, a stereoisomer of the compound or a pharmaceutically acceptable salt thereof according to claim 1 .
20. A method for treating pulmonary hypertension comprising administering to a patient in need thereof a therapeutically effective amount of a compound, a pharmaceutically acceptable salt thereof, a stereoisomer of the compound or a pharmaceutically acceptable salt thereof according to claim 1 .
21. A method for treating pulmonary hypertension comprising administering to a patient in need thereof a therapeutically effective amount of a compound, a pharmaceutically acceptable salt thereof, a stereoisomer of the compound or a pharmaceutically acceptable salt thereof according to claim 4 .
22. A method for treating pulmonary hypertension comprising administering to a patient in need thereof a therapeutically effective amount of a compound, a pharmaceutically acceptable salt thereof, a stereoisomer of the compound or a pharmaceutically acceptable salt thereof according to claim 5 .
23. A method for treating pulmonary hypertension comprising administering to a patient in need thereof a therapeutically effective amount of a compound, a pharmaceutically acceptable salt thereof, a stereoisomer of the compound or a pharmaceutically acceptable salt thereof according to claim 6 .
24. A method for treating pulmonary hypertension comprising administering to a patient in need thereof a therapeutically effective amount of a compound, a pharmaceutically acceptable salt thereof, a stereoisomer of the compound or a pharmaceutically acceptable salt thereof according to claim 7 .
25. A method for treating pulmonary hypertension comprising administering to a patient in need thereof a therapeutically effective amount of a compound, a pharmaceutically acceptable salt thereof, a stereoisomer of the compound or a pharmaceutically acceptable salt thereof according to claim 8 .
26. A method for treating pulmonary hypertension comprising administering to a patient in need thereof a therapeutically effective amount of a compound, a pharmaceutically acceptable salt thereof, a stereoisomer of the compound or a pharmaceutically acceptable salt thereof according to claim 9 .
27. A method for treating pulmonary hypertension comprising administering to a patient in need thereof a therapeutically effective amount of a compound, a pharmaceutically acceptable salt thereof, a stereoisomer of the compound or a pharmaceutically acceptable salt thereof according to claim 10 .