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US 2010/0063108 A1Published application
Pyridin-4-yl derivatives as immunomodulating agents
AssigneeActelion Pharmaceuticals Ltd.
InventorsMartin Bolli, David Lehmann, Boris Mathys, Claus Mueller, Oliver Nayler, Beat Steiner, Jorg Velker
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Abstract
The invention relates to pyridine derivatives of Formula (I) wherein A, R1, R2, R3, R4, R5, and R6 are as described in the description, their preparation and their use as pharmaceutically active compounds. Said compounds particularly act as immunomodulating agents.
Claims24
A compound of the Formula (I),
- wherein
- A represents *—CONH—CH2—, *—CO—CH═CH—, *—CO—CH2CH2—,
- wherein the asterisks indicate the bond that is linked to the pyridine group of Formula (I);
- R1 represents C1-4-alkyl, or chloro;
- R2 represents C1-5-alkyl, C1-4-alkoxy, or C3-6-cycloalkyl;
- R3 represents hydrogen, C1-4-alkyl, C1-4-alkoxy, or halogen;
- R4 represents hydrogen, C1-4-alkyl, C1-4-alkoxy, halogen, trifluoromethyl, or trifluoromethoxy;
- 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, —CO—NHR51, 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, 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, —OCH2—CH(OH)—CH2—NHCOR54;
- R51 represents hydrogen, C1-3-alkyl, 2-hydroxyethyl, 2-hydroxy-1-hydroxymethyl-ethyl, 2,3-dihydroxypropyl, carboxymethyl, 1-(C1-5-alkylcarboxy)methyl, 2-carboxyethyl, or 2-(C1-5-alkylcarboxy)ethyl;
- R52 represents hydrogen, methyl, or ethyl;
- R53 represents C1-3-alkyl, methylamino, ethylamino, or dimethylamino;
- R54 represents hydroxymethyl, hydroxyethyl, aminomethyl, methylaminomethyl, dimethylaminomethyl, aminoethyl, 2-methylamino-ethyl, or 2-dimethylamino-ethyl;
- 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;
- in free or salt form.
15 more elements
Dependencies are inferred from the claim text.