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US 2005/0032797 A1Published application
Fluorinated di-aryl urea compounds
AssigneeBoehringer Ingelheim Pharmaceuticals, Inc.
InventorsPier Cirillo, Abdelhakim Hammach, Victor Kamhi, Neil Moss, Paul Riska, Christopher Pargellis
Life of this patent
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Abstract
Disclosed are compounds of formula(I): wherein R1, R2, W and X of formula(I) are defined herein. The compounds inhibit production of cytokines involved in inflammatory processes and are thus useful for treating diseases and pathological conditions involving inflammation such as chronic inflammatory disease. Also disclosed are processes for preparing these compounds and pharmaceutical compositions comprising these compounds.
Claims12
A compound of the formula (I):
- wherein
- R1 is —CF3, —CH(CH3)(CF3), —CH(CF3)2, —OCF3, —CF2CF3;
- R2 is C1-5 alkyl;
- R3 is attached at the 3- or 4-position on the phenyl ring and is hydrogen, —NH2 or R4—S(O)2—NH— wherein R4 is chosen from C1-5 alkyl or carbocycle;
- W is CH or an N atom;
- X is chosen from
- C1-5 alkyl or C1-5 alkoxy each substituted by morpholinyl, piperazinyl, pyrrolidinyl, triazolyl, imidazolyl or piperadinyl each ring being further optionally substituted with C1-3 alkyl;
- or X is —NHRa wherein Ra is heterocyclyl C1-3 alkyl wherein the heterocycyl is chosen from tetrahydroftiran, pyrrolidinyl and morpholinyl, each optionally substituted by one to two C1-5 alkyl, C1-5 alkoxy, hydroxy, halogen or amino optionally mono- or di-substituted by C1-3 alkyl;
- or the pharmaceutically acceptable acids, esters, salts or isomers thereof.
6 more elements
A compound chosen from:
- 1-(2-Methoxy-5-trifluoromethyl-phenyl)-3-[4-(6-methyl-2-
- morpholin-4-ylmethyl-pyrimidin-4-yloxy)-naphthalen-1-yl]-
- urea;
- 1-(2-Methoxy-5-trifluoromethyl-phenyl)-3-(4-{6-methyl-2-
- [(tetrahydro-furan-2-ylmethyl)-amino]-pyrimidin-4-yloxy}-
- naphthalen-1-yl)-urea;
- 1-(2-Methoxy-5-trifluoromethyl-phenyl)-3-{4-[6-methyl-2-(2-
- pyrrolidin-1-yl-ethylamino)-pyrimidin-4-yloxy]-naphthalen-1-
- yl}-urea and
- 1-(2-Methoxy-5-trifluoromethyl-phenyl)-3-{4-[6-methyl-2-(2-
- morpholin-4-yl-ethylamino)-pyrimidin-4-yloxy]-naphthalen-1-
- yl}-urea
- or the pharmaceutically acceptable acids, esters, salts or isomers thereof.
10 more elements
A compound chosen from:
- 1-(2-Methoxy-5-trifluoromethoxy-phenyl)-3-{4-[6-methyl-2-
- (2-pyrrolidin-1-yl-ethylamino)-pyrimidin-4-yloxy]-naphthalen-
- 1-yl}-urea;
- 1-(2-Methoxy-5-trifluoromethoxy-phenyl)-3-[4-(6-methyl-2-
- morpholin-4-ylmethyl-pyrimidin-4-yloxy)-naphthalen-1-yl]-
- urea;
- 1-(2-Methoxy-5-trifluoromethoxy-phenyl)-3-{4-[6-methyl-2-
- (4-methyl-piperazin-1-ylmethyl)-pyrimidin-4-yloxy]-
- naphthalen-1-yl}-urea;
- 1-(2-Methoxy-5-trifluoromethoxy-phenyl)-3-[4-(6-methyl-2-
- pyrrolidin-1-ylmethyl-pyrimidin-4-yloxy)-naphthalen-1-yl]-
- urea;
- 1-{4-[2-(2-Imidazol-1-yl-ethoxy)-6-methyl-pyrimidin-4-yloxy]-
- naphthalen-1-yl}-3-(2-methoxy-5-trifluoromethoxy-phenyl)-
- urea;
- 1-[2-Methoxy-5-(2,2,2-trifluoro-ethyl)-phenyl]-3-{4-[6-methyl-
- 2-(1-methyl-piperidin-4-ylmethoxy)-pyrimidin-4-yloxy]-
- naphthalen-1-yl}-urea;
- 1-[2-Methoxy-5-(2,2,2-trifluoro-ethyl)-phenyl]-3-{4-[6-methyl-
- 2-(3-morpholin-4-yl-propylamino)-pyrimidin-4-yloxy]-
- naphthalen-1-yl}-urea;
- 1-(2-Methoxy-5-trifluoromethoxy-phenyl)-3-{4-[6-methyl-2-
- (3-morpholin-4-yl-propylamino)-pyrimidin-4-yloxy]-
- naphthalen-1-yl}-urea;
- 1-[2-Methoxy-5-(2,2,2-trifluoro-1-trifluoromethyl-ethyl)-
- phenyl]-3-[4-(6-methyl-2-morpholin-4-ylmethyl-pyrimidin-4-
- yloxy)-naphthalen-1-yl]-urea and
- 1-(2-Methoxy-5-trifluoromethyl-phenyl)-3-{4-[6-methyl-2-(4-
- methyl-piperazin-1-ylmethyl)-pyrimidin-4-yloxy]-naphthalen-
- 1-yl}-urea
- or the pharmaceutically acceptable acids, esters, salts or isomers thereof.
28 more elements
A compound chosen from
- 1-(2-Methoxy-5-trifluoromethyl-phenyl)-3-[4-(6-methyl-2-
- morpholin-4-ylmethyl-pyrimidin-4-yloxy)-naphthalen-1-yl]-
- urea;
- 1-(2-Methoxy-5-trifluoromethyl-phenyl)-3-{4-[6-methyl-2-(2-
- pyrrolidin-1-yl-ethylamino)-pyrimidin-4-yloxy]naphthalen-1-
- yl}-urea;
- and
- 1-(2-Methoxy-5-trifluoromethyl-phenyl)-3-{4-[6-methyl-2-(2-
- morpholin-4-yl-ethylamino)-pyrimidin-4-yloxy]-naphthalen-1-
- yl}-urea
- or the pharmaceutically acceptable acids, esters, salts or isomers thereof.
8 more elements
Dependencies are inferred from the claim text.