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US 8,133,910 B2Granted
Thiophene derivatives as S1P1/EDGE1 receptor agonists
AssigneeActelion Pharmaceuticals Ltd.
InventorsMartin Bolli, David Lehmann, Boris Mathys, Claus Mueller, Oliver Nayler, Beat Steiner, Jörg Velker
Life of this patent
Estimating the term…
Abstract
The invention relates to novel thiophene derivatives, their preparation and their use as pharmaceutically active compounds. Said compounds particularly act as immunomodulating agents.
Claims21
A compound of the Formula (I),
- wherein
- A represents *—CO—CH2CH2—, *—CO—CH═CH—,
- wherein the asterisks indicate the bond that is linked to the thiophene group of Formula (I);
- R1 represents C2-5-alkyl;
- R2 represents hydrogen, methyl or ethyl;
- R3 represents hydrogen;
- R4 represents methyl, ethyl, or methoxy;
- R5 represents —CH2—(CH2)n—NHSO2R51, —(CH2)nCH(OH)—CH2—NHSO2R51, —CH2—(CH2)n—NHCOR52, —(CH2)nCH(OH)—CH2—NHCOR52, —CH2—(CH2)n—CONR53R54, —CO—NHR53, 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, hydroxy, hydroxy-C2-5-alkoxy, di-(hydroxy-C1-4-alkyl)-C1-4-alkoxy, 2,3-dihydroxypropoxy, 2-hydroxy-3-methoxy-propoxy, —OCH2—(CH2)m—NHSO2R51, —OCH2—CH(OH)—CH2—NHSO2R51, —OCH2—(CH2)m—NHCOR52, or —OCH2—CH(OH)—CH2—NHCOR52;
- R51 represents C1-3-alkyl, methylamino, ethylamino, or dimethylamino;
- R52 represents hydroxymethyl, 2-hydroxyethyl, 2-hydroxy-1-hydroxymethyl-ethyl, or 2,3-dihydroxypropyl;
- R53 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;
- R54 represents hydrogen, or methyl;
- m represents the integer 1 or 2;
- n represents 0, 1, or 2;
- and
- R6 represents methyl, ethyl or halogen;
- in free or salt form.
14 more elements
Dependencies are inferred from the claim text.