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US 2003/0144281 A1Published application
Substituted benzimidazole compounds
AssigneeBoehringer Ingelheim Pharmaceuticals, Inc.
InventorsCharles Cywin, Jinbo Lee, Steven S. Pullen, Gregory Paul Roth, Christopher Ronald Sarko, Roger John Snow, Noel Stewart Wilson
Life of this patent
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Abstract
Disclosed are substituted benzimidazole compounds of formula(I): 1 wherein R1, R2, R3, R4 and Xa are defined herein. The compounds of the invention are useful for treating diseases and pathological conditions involving inflammation, immunological disorders and allergic disorders. Also disclosed are processes for preparing these compounds and to pharmaceutical compositions comprising these compounds.
Claims18
A compound of the formula (1):
- 35
- wherein:
- R1 is hydrogen or alkyl;
- R2 is chosen from aryl and heteroaryl each R2 is optionally substituted with one or more Ra;
- R3 is C1-10 alkyl chain branched or unbranched optionally substituted with one or more Rb,
- or R3 is the group:
- —(CH2)n-L-R6, wherein L is chosen from a bond, —NH—C(O)—, —O—C(O)—, —C(O)— and —S(O)m— wherein m is 0, 1 or 2, and wherein said group is optionally substituted by one or more Rb;
- wherein R6 is independently chosen from hydroxy, alkyl, alkoxy, alkylthio, arylC0-5 alkyl, aryloxyC0-5 alkyl, heteroarylC0-5 alkyl, cycloalkylC0-5 alkyl, heterocyclylC0-5 alkyl and amino said amino is optionally mono- or di-substituted by acyl, alkyl, alkoxycarbonyl, cycloalkylC0-5 alkyl, arylC0-5 alkyl, heteroarylC0-5 alkyl or heterocyclylC0-5 alkyl;
- n is 1-10;
- R4 is the group:
- 36
- wherein R4 is covalently attached at the indicated 5- or 6-position of the formula (I);
- R5 is chosen from arylC0-5 alkyl, alkyl, heteroarylC0-5 alkyl, cycloalkylC0-5 alkyl and heterocyclylC0-5 alkyl, each R5 optionally substituted with one or more Rc;
- R7 is hydrogen, alkenyl or alkyl;
- or R5 and R7 together with the nitrogen atom to which they are attached form:
- a 4-7-membered monocyclic ring or
- an 8-14-membered bicyclic ring,
- wherein each monocyclic or bicyclic ring optionally contains an additional 1 to 3 heteroatoms chosen from N, O and S and each ring is aromatic or nonaromatic, and wherein each monocyclic or bicyclic ring is optionally substituted by one or more Rc;
- each Ra, Rb or Rc are independently chosen from hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, arylalkyl, aryloxy, alkoxy, alkylthio, acyl, alkoxycarbonyl, acyloxy, acylamino, sulphonylamino, aminosulfonyl, alkylsulfonyl, carboxy, carboxamide, hydroxy, halogen, trifluoromethyl, nitro, nitrile and amino optionally mono- or -di-substituted by alkyl, acyl or alkoxycarbonyl, wherein any of the above Ra, Rb or Rc are optionally halogenated where possible;
- and
- Xa and Xb are oxygen or sulfur;
- or the pharmaceutically acceptable salts, esters, isomers or tautomers thereof.
19 more elements
A compound chosen from:
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- or the pharmaceutically acceptable salts, esters, isomers or tautomers thereof.
A compound chosen from:
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- or the pharmaceutically acceptable salts, esters, isomers or tautomers thereof.
Dependencies are inferred from the claim text.