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US 8,299,086 B2Granted
Pyrimidine derivatives
AssigneeActelion Pharmaceuticals Ltd.
InventorsMartin Bolli, Cyrille Lescop, Boris Mathys, Claus Mueller, Oliver Nayler, Beat Steiner
Life of this patent
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Abstract
The invention relates to novel pyrimidine derivatives, their preparation and their use as pharmaceutically active compounds. Said compounds particularly act as immunomodulating agents. Formula (I) wherein A represents Formula (II), Formula (III), Formula (IV), Formula (V), Formula (VI), Formula (VII), Formula (VIII) or Formula (IX)
Claims13
A compound of the formula (I)
- wherein
- A represents
- wherein the asterisks indicate the bond that is linked to the pyrimidine group of formula (I);
- R1 represents C1-4-alkoxy, C1-4-alkylamino, N—C1-4-alkyl-N—C1-3-alkylamino, C3-5-cycloalkylamino, C3-5-cycloalkylmethylamino, pyrrolidine, or piperidine;
- R2 represents C1-2-alkyl or C3-4-alkyl;
- R3 represents hydrogen, C1-4-alkyl, or C1-3-alkoxy;
- R4 represents hydrogen, C1-4-alkyl, or C1-3-alkoxy;
- R5 represents 2,3-dihydroxypropyl, di-(hydroxy-C1-4-alkyl)-C1-4-alkyl, —CH2—(CH2)k—NHSO2R53, —(CH2)nCH(OH)—CH2—NHSO2R53, —CH2—(CH2)k—NHCOR54, —(CH2)nCH(OH)—CH2—NHCOR54, —CH2—(CH2)n—CONR51R52, 1-(3-carboxy-azetidinyl)-2-acetyl, 1-(2-carboxy-pyrrolidinyl)-2-acetyl, 1-(3-carboxy-pyrrolidinyl)-2-acetyl, 1-(3-carboxy-azetidinyl)-3-propionyl, 1-(2-carboxy-pyrrolidinyl)-3-propionyl, 1-(3-carboxy-pyrrolidinyl)-3-propionyl, —(CH2)nCH(OH)—CH2—NR51R52, hydroxy-C2-5-alkoxy, di-(hydroxy-C1-4-alkyl)-C1-4-alkoxy, 2,3-dihydroxy-propoxy, 2-hydroxy-3-methoxy-propoxy, —OCH2—(CH2)m—NR51R52, 2-[(azetidine-3-carboxylic acid)-1-yl]-ethoxy, 2-[(azetidine-3-carboxylic acid C1-5-alkylester)-1-yl]-ethoxy, 2-[(pyrrolidine-3-carboxylic acid)-1-yl]-ethoxy, 2-[(pyrrolidine-3-carboxylic acid C1-5-alkylester)-1-yl]ethoxy, —OCH2—CH(OH)—CH2—NR51R52, 3-[(azetidine-3-carboxylic acid)-1-yl]-2-hydroxypropoxy, 3-[(azetidine-3-carboxylic acid C1-5-alkylester)-1-yl]-2-hydroxypropoxy, 2-hydroxy-3-[(pyrrolidine-3-carboxylic acid)-1-yl]-propoxy, 2-hydroxy-3-[(pyrrolidine-3-carboxylic acid C1-5-alkylester)-1-yl]-propoxy, 2-hydroxy-3-[(pyrrolidine-2-carboxylic acid)-1-yl]-propoxy, 2-hydroxy-3-[(pyrrolidine-2-carboxylic acid C1-5-alkylester)-1-yl]-propoxy, —OCH2—(CH2)m—NHSO2R53, —OCH2—CH(OH)—CH2—NHSO2R53, —OCH2—(CH2)m—NHCOR54, or —OCH2—CH(OH)—CH2—NHCOR54;
- R51 represents hydrogen, C1-3-alkyl, 2-hydroxyethyl, 2-hydroxy-1-hydroxymethyl-ethyl, 2,3-dihydroxypropyl, carboxymethyl, (C1-5-alkylcarboxy)methyl, 2-carboxyethyl, 2-(C1-5-alkylcarboxy)ethyl, or 2-aminoethyl;
- R52 represents hydrogen, methyl, or ethyl;
- R53 represents C1-3-alkyl, methylamino, ethylamino, or dimethylamino;
- R54 represents hydroxy-C1-2-alkyl or R55R56N—C1-2-alkyl;
- R55 and R56 independently represent hydrogen or methyl;
- k represents the integer 1, 2, or 3;
- m represents the integer 1 or 2;
- n represents 0, 1, or 2;
- and
- R6 represents hydrogen, C1-4-alkyl, or halogen;
- or a salt of such a compound.
16 more elements
Dependencies are inferred from the claim text.