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US 8,410,151 B2Granted
Aminomethyl benzene derivatives
AssigneeActelion Pharmaceuticals Ltd.
InventorsMartin Bolli, Cyrille Lescop, Boris Mathys, Claus Mueller, Oliver Nayler, Beat Steiner
Life of this patent
Estimating the term…
Abstract
The invention relates to novel aminomethyl benzene derivatives, their preparation and their use as pharmaceutically active compounds. Said compounds particularly act as immunomodulating agents.
Claims10
A compound of formula (I)
- wherein
- A represents
- wherein the asterisks indicate the bond that is linked to the phenyl group bearing the substituents R1, R2 and R3;
- R1 represents —CH2—NR1aR1b, R2 represents hydrogen, and R3 represents hydrogen, C1-4 alkyl, or C1-3-alkoxy;
- or
- R1 represents —CH2—NR1aR1b, R2 represents C1-4-alkyl or C1-3-alkoxy, and R3 represents hydrogen or methyl;
- or
- R1 represents hydrogen, C1-4-alkyl or C1-3-alkoxy, R2 represents —CH2—NR2aR2b, and R3 represents hydrogen or methyl;
- R1a represents C1-4-alkyl,
- R1b represents hydrogen, or C1-2-alkyl, or R1a and R1b together with the nitrogen atom to which they are attached form a pyrrolidine ring;
- R2a represents C1-4-alkyl,
- R2b represents hydrogen, or C1-2-alkyl, or R2a and R2, together with the nitrogen atom to which they are attached form a pyrrolidine ring;
- R4 represents hydrogen, methyl, methoxy or chloro;
- R5 represents hydrogen, C1-3-alkyl, methoxy, fluoro or chloro;
- R6 represents 2,3-dihydroxypropyl, —CH2—(CH2)n—NR61R62, —CH2—(CH2)n—NHCOR64, —CH2—(CH2)n—NHSO2R63, —CH2—CH2—COOH, —CH2—CH2—CONR61R62, 1-(3-carboxy-azetidinyl)-3-propionyl, 1-(2-carboxy-pyrrolidinyl)-3-propionyl, 1-(3-carboxy-pyrrolidinyl)-3-propionyl, —CH2—CH(OH)—CH2—NR61R62, —CH2—CH(OH)—CH2—NHCOR64, —CH2—CH(OH)—CH2—NHSO2R63, hydroxy, hydroxy-C2-4-alkoxy, 1-hydroxymethyl-2-hydroxy-ethoxy, 2,3-dihydroxypropoxy, —OCH2—(CH2)m—NR61R62, —OCH2—(CH2)m—NHCOR64, —OCH2—(CH2)m—NHSO2R63, 2-[(azetidine-3-carboxylic acid)-1-yl]-ethoxy, 2-[(pyrrolidine-2-carboxylic acid)-1-yl]-ethoxy, 2-[(pyrrolidine-3-carboxylic acid)-1-yl]-ethoxy, —OCH2—CH(OH)—CH2—NR61R62, —OCH2—CH(OH)—CH2—NHCOR64, —OCH2—CH(OH)—CH2—NHSO2R63, 3-[(azetidine-3-carboxylic acid)-1-yl]-2-hydroxypropoxy, 2-hydroxy-3-[(pyrrolidine-2-carboxylic acid)-1-yl]-propoxy, 2-hydroxy-3-[(pyrrolidine-3-carboxylic acid)-1-yl]-propoxy, —NR61R62, —NHCO—R64;
- R61 represents hydrogen, methyl, ethyl, 2-hydroxyethyl, 3-hydroxypropyl, 2-aminoethyl, 2-(C1-4-alkylamino)ethyl, 2-(di-(C1-4-alkyl)amino)ethyl, carboxymethyl, (C1-4-alkylcarboxy)methyl, 2-carboxyethyl, or 2-(C1-4-alkylcarboxy)ethyl;
- R62 represents hydrogen or methyl;
- R63 represents methyl, ethyl, methylamino, or dimethylamino;
- R64 represents hydroxymethyl, 2-hydroxyethyl, methylaminomethyl, dimethylaminomethyl, or 2-methylamino-ethyl;
- m represents the integer 1 or 2;
- n represents 0, 1 or 2;
- and
- R7 represents hydrogen, or C1-2-alkyl;
- or a pharmaceutically acceptable salt thereof.
21 more elements
Dependencies are inferred from the claim text.