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US 7,410,972 B2Granted
Compounds
AssigneeAstraZeneca AB
InventorsAndrew Baxter, Timothy Johnson, Nicholas Kindon, Bryan Roberts, John Steele, Michael Stocks, Nicholas Tomkinson
Life of this patent
Estimating the term…
Abstract
The invention provides N-pyrazinyl-thienylsulphonamides of formula (I) for use in the treatment of chemokine mediated diseases. Particularly inflammatory diseases, such as asthma
Claims16
A compound of formula (I) or a pharmaceutically acceptable salt thereof:
- in which:
- R1, R2 and R3 are independently hydrogen, halogen, cyano, CF3, or C1-6 alkyl;
- R4is
- halogen, CO2R12,
- C1-6 alkoxy where the alkyl group may form a 3-6 membered saturated ring or may be substituted with 1-3 fluorine atoms or a cyano group;
- C3-6 alkenyloxy or C3-6 alkynyloxy where either may be optionally substituted with hydroxy or NR14R15;
- OC1-6 alkyl-X—C1-6 alkyl where the alkyl groups may form a 3-6 membered saturated ring;
- OC1-6 alkylR11, or OC2-6 alkyl-X—R11 where the alkyl group may form a 3-6 membered saturated ring and is optionally substituted with 1-3 groups selected from hydroxy, halogen, NR14R15, SR13, S(O)2R13, S(O)13;
- OC1-6 alkylR16;
- R5 and R6 are independently
- hydrogen, cyano, halogen, CO2R12, CONR14R15;
- C1-6 alkyl optionally substituted by hydroxy, NR14R15, or 1-3 fluorines;
- C1-6 alkylR11 or XCH(R11)C1-6 alkyl or XCH(R16)C1-6 alkyl where the alkyl group may be optionally substituted with 1-3 groups selected from hydroxy, and NR14R15;
- NR14R15;
- N(R11)R11;
- X—(CH2)qNR14R15;
- (CH2)nNR14R15;
- C3-6 alkynyl or C3-6 alkenyl optionally branched and optionally substituted with 1-3 groups selected from hydroxy, cyano, halogen and ═O;
- R11;
- X—R11;
- X—R12;
- X—C1-6alkylR16;X—R16;
- X—(CH2)nCO2R12;
- X—(CH2)nCONR14R15;
- X—(CH2)nR11;
- X—(CH2)nCN;
- X—(CH2)qOR12;
- (CH2)nOR12;
- (CH2)n-X—R11;
- X—(CH2)qNHC(O)NHR12;
- X—(CH2)qNHC(O)R12;
- X—(CH2)qNHS(O)2R12;
- X—(CH2)qNHS(O)2R11;
- X—C3-6 alkenyl;
- X—C3-6 alkynyl;
- n is 1 ,2, 3, 4 or 5;
- q is 2, 3, 4, 5 or 6;
- X is NR13, O, S, S(O), S(O)2;
- R11 is
- an aryl group or a 5-7 membered heteraromatic ring containing 1-4 heteroatoms selected from nitrogen, oxygen or sulphur each of which can be optionally substituted by 1-3 groups selected from halogen, C(O)NR14R15, C(O)OR12, hydroxy, ═O,═S, CN, NO2,
- NR14R15, X(CH2)qNR14R15, (CH2)nNR14R15, (CH2)nOH, SR13, S(O)R13, S(O)2R13 C1-6 alkyl-X—C1-6 alkyl, C1-6 alkyl or C1-6 alkoxy where the alkyl group may form a 3-6 membered ring or is optionally substituted with 1-3 groups selected from hydroxy, halogen, NR14R15, SR13, S(O)R13, S(O)2R13;
- R12 and R13 are independently hydrogen or C1-6 alkyl where the alkyl group may be substituted with 1-3 fluorine atoms or may form a saturated 3-6 membered ring;
- R14 and R15 are independently hydrogen, C1-6 alkyl, C3-6 cycloalkyl or (CH2)qOH, or R14 and R15 together with the nitrogen atom to which they are attached form a 4-8 membered saturated ring containing 1-3 heteroatoms selected from nitrogen, oxygen and sulphur and optionally substituted by C1-6 alkyl, C1-6 alkyl-OH, or hydroxy;
- and
- R16 is a 4-8 membered saturated ring containing 1-3 heteroatoms selected from nitrogen, oxygen or sulphur and optionally substituted with 1-3 groups selected from hydroxy, cyano, halogen and ═O.
42 more elements
A compound of formula (IA)
- in which:
- R1, R2 and R3 are independently hydrogen, C1-6 alkyl or halogen;
- R4 is halogen, C1-6 alkoxy or OR9;
- R5 and R6 are independently hydrogen, halogen, C1-6 alkoxy, C1-6 alkylthio, cyano,R9, OR9, NR9R10, SR9, S(CH2)nCO2H, S(CH2)nCO2R12, S(CH2)nCONR12R13, S(CH2)nR11 or a 5- to 7-membered heteroaromatic or saturated ring containing 1 to 3 heteroatoms selected from nitrogen, oxygen and sulphur;
- n is 1,2 or 3;
- R9 and R10 are independently hydrogen, C1-6 alkyl optionally substituted by hydroxy, C1-6 alkoxy or NHCOC1-6 alkyl, or R9 and R10 optionally substituted aryl, C1-6 alkyl-aryl or C1-6 alkyl-R11 or R9 and R10 together with the nitrogen atom to which they are attached form a 4- to 8-membered saturated ring containing 1 to 3 heteroatoms selected from nitrogen, oxygen and sulphur and optionally substituted by C1-6 alkyl or C1-6 alkyl-OH;
- and
- R11 is a 5- to 7-membered heteraromatic ring containing 1 to 3 heteroatoms selected from nitrogen, oxygen and sulphur and optionally substituted by C1-6 alkyl;
- and
- R12 and R13 are independently hydrogen or C1-6 alkyl.
7 more elements
Dependencies are inferred from the claim text.