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US 2010/0168005 A1Published application
Pyridin-3-yl derivatives as immunomodulating agents
AssigneeActelion Pharmaceuticals Ltd.
InventorsMartin Bolli, David Lehmann, Boris Mathys, Claus Mueller, Oliver Nayler, Beat Steiner
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Abstract
The invention relates to pyridin-3-yl derivatives of Formula (I) wherein R1, R2, R3, R4, R5; R6 and A are as described in the description, their preparation and their use as pharmaceutically active compounds. Said compounds particularly act as immunomodulating agents.
Claims23
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 hydrogen, C1-4-alkyl, or chloro;
- R2 represents C1-5-alkyl or C1-4-alkoxy;
- 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)CH(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)—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.