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US 2003/0153567 A1Published application
Endothelin receptor antagonists
AssigneeSmithKline Beecham Corporation
InventorsJohn Duncan Elliott, Joseph Weinstock, Jia-Ning Xiang
Life of this patent
Estimating the term…
Abstract
Novel N-phenyl imidazole derivatives, pharmaceutical compositions containing these compounds and their use as endothelin receptor antagonists are described.
Claims16
A compound of Formula (I):
- 27
- wherein:
- R1 is H, C1-6alkyl or C1-6alkoxy;
- R2 is XR5, —R8CO2R4, —(CH2)xC(O)N(R4)S(O)yR9, —(CH2)xS(O)yN(R4)C(O)R9, —(CH2)xC(O)N(R4)C(O)R9, —(CH2)nR7, —(CH2)xS(O)yN(R4)S(O)yR9 or Ar;
- X is O, S or NR4;
- R3 is C1-10alkyl, XC1-10alkyl, Ar or XAr;
- R4 is hydrogen or C1-6alkyl;
- R5 is —R8CO2R4, —(CH2)xC(O)N(R4)S(O)yR9, —(CH2)xS(O)yN(R4)C(O)R9, —C(O)N(R4)2, —(CH2)xC(O)N(R4)C(O)R9, —(CH2)nCO2R4, —(CH2)xS(O)yN(R4)S(O)yR9, —(CH2)nR7, or Ar;
- R6 is C1-8alkyl or —Ar;
- P is tetrazol-5-yl, CO2R4 or C(O)N(R4)S(O)yR9;
- R7 is C1-6 alkoxy, C1-6alkyl, hydroxy, —SC1-6alkyl, —NHSO2R9, SO2NHR9, —SO3H, —CO(NR4)2, CN, —S(O)yC1-6alkyl, —PO(OR4)2, —N(R4)2, —NR4CHO, —NR4COC1-6alkyl, —NR4CON(R4)2 or Ar, or R7 is tetrazolyl, which is substituted or unsubstituted by C1-6alkyl, CF3 or C(O)R3;
- R8 is C1-4alkylene, C1-4alkenylene or C1-4alkylidene, all of which may be linear or branched;
- R9 is C1-10alkyl, N(C1-8alkyl)2 or Ar;
- n is 1 to 4;
- m is 0 to 3;
- x is 0 to 4;
- y is 1 or 2;
- Ar is:
- 28
- naphthyl, indolyl, pyridyl, thienyl, oxazolidinyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, imidazolinyl, thiazolidinyl, isoxazolyl, oxadiazolyl, thiadiazolyl, morpholinyl, piperidinyl, piperazinyl, pyrrolyl, or pyrimidyl;
- all of which may be substituted or unsubstituted by one or more Z1 or Z2 groups;
- Z1 and Z2 are independently hydrogen, XR4, C1-8alkyl, CO2R4, C(O)N(R4)2, CN, NO2, F, Cl, Br, I, N(R4)2, NHC(O)R4 or tetrazolyl which may be substituted or unsubstituted by C1-6alkyl, CF3 or C(O)R4;
- A is C═O or [C(R4)2]q;
- B is —CH2— or —O—;
- and
- q is 1 or 2:
- and the dotted line indicates the optional presence of a double bond;
- or a pharmaceutically acceptable salt thereof;
- provided:
- R6 is not thienyl;
- and
- R2 is not (CH)nC1-6 alkyl, or —CH═CHCO2R4.
29 more elements
Dependencies are inferred from the claim text.