2-sulfanyl-benzoimidazol-1-yi-acetic acid derivatives as CRTH2 antagonists

A compound of the formula I:

• wherein
• R1, R2, R3 and R4 each independently represent hydrogen;
• alkyl;
• haloalkyl;
• halogen;
• nitro;
• cyano;
• formyl;
• methylsulfonyl;
• or methylcarbonyl;
• n is 0 or an integer from 1 to 10;
• r is 0 or 1;
• R5, R6 and R7 each independently represent hydrogen;
• alkyl;
• alkenyl;
• cycloalkyl;
• aryl;
• aryloxy;
• alkylcarbonyl;
• cycloalkylcarbonyl;
• arylcarbonyl;
• arylalkylcarbonyl;
• N-alkyl-N-aryl-carbamoyl;
• N-alkyl-N-arylalkyl-carbamoyl;
• N-arylalkyl-N-aryl-carbamoyl;
• heterocyclyl;
• heterocyclyloxy;
• heterocyclylcarbonyl;
• or an amino of Formula NR8R9;
• or two of R5-R7 together with the carbon atom to which they are attached form cycloalkyl or saturated heterocyclyl;
• R8 represents hydrogen or R9;
• R9 independently from R8 represents cycloalkyl;
• cycloalkylalkyl;
• aryl;
• cycloalkylarylalkyl;
• arylalkyl;
• (diaryl)-alkyl;
• alkylcarbonyl;
• alkenylcarbonyl;
• cycloalkylcarbonyl;
• cycloalkylalkylcarbonyl;
• alkoxycarbonyl;
• alkoxydicarbonyl;
• arylcarbonyl;
• arylalkylcarbonyl;
• arylalkenylcarbonyl;
• (diaryl)-alkylcarbonyl;
• cycloalkylarylalkylcarbonyl;
• heterocyclylcarbonyl;
• alkylcarbamoyl;
• arylcarbamoyl;
• arylalkylcarbamoyl;
• alkylsulfonyl;
• arylsulfonyl;
• arylalkylsulfonyl;
• or
• R8 and R9, together with the nitrogen atom to which they are attached, form a heterocyclyl group;
• and
• R11 is hydrogen or methyl;
• wherein aryl groups present as R5-R9, alone or in combination, are unsubstituted or mono- or di-substituted with substituents independently selected from lower alkyl;
• hydroxy-lower alkyl;
• lower alkoxy;
• lower alkoxy-lower alkyl;
• halogen;
• cyano;
• lower alkylcarbonyl;
• aryl;
• aryl-lower alkyl;
• cycloalkyl;
• 2,3-dihydro-indole-1-carbonyl;
• lower alkylcarbamoyl;
• morpholine-4-carbonyl;
• aryl-lower alkylcarbamoyl;
• N,N-di-lower alkylcarbamoyl;
• N-lower alkyl-N-aryl-lower alkyl-carbamoyl;
• hydroxy-lower alkoxy;
• arylcarbonyl;
• or heterocyclyl;
• or a pharmaceutically acceptable salt of the compound;
• or an optically pure enantiomer, a mixture of enantiomers, a racemate, an optically pure diastereoisomer, a mixture of diastereoisomers, a diastereoisomeric racemate, a mixture of diastereoisomeric racemates, a meso form, a geometric isomer, or pharmaceutically acceptable salts thereof,
• wherein the following compounds are excluded:
• (2-octylsulfanyl-benzoimidazol-1-yl)-acetic acid;
• (2-butylsulfanyl-benzoimidazol-1-yl)-acetic acid;
• (2-propylsulfanyl-benzoimidazol-1-yl)-acetic acid;
• (2-ethylsulfanyl-benzoimidazol-1-yl)-acetic acid;
• (2-methylsulfanyl-benzoimidazol-1-yl)-acetic acid;
• (2-isopropylsulfanyl-benzoimidazol-1-A-acetic acid;
• (2-sec-butylsulfanyl-benzoimidazol-1-yl)-acetic acid;
• (2-isobutylsulfanyl-benzoimidazol-1-yl)-acetic acid;
• (2-allylsulfanyl-benzoimidazol-1-yl)-acetic acid;
• (2-cyclohexylsulfanyl-benzoimidazol-1-yl)-acetic acid;
• (2-benzylsulfanyl-benzoimidazol-1-yl)-acetic acid;
• (2-phenethylsulfanyl-benzoimidazol-1-yl(-acetic acid;
• [2-(naphthalen-1-ylmethylsulfanyl)-benzoimidazol-1-yl]-acetic acid;
• {2-[2-(4-tert-butyl-phenoxy)-ethylsulfanyl]-benzoimidazol-1-yl}-acetic acid;
• {2-[2-(4-propoxy-phenoxy)-ethylsulfanyl]-benzoimidazol-1-yl}-acetic acid;
• {2-[2-(4-ethoxy-phenoxy)-ethylsulfanyl]-benzoimidazol-1-yl}-acetic acid;
• {2-[2-(3,4-dimethyl-phenoxy)-ethylsulfanyl]-benzoimidazol-1-yl}-acetic acid;
• {2-[2-(3-methylphenoxy)-ethylsulfanyl]-benzoimidazol-1-yl}-acetic acid;
• {2-[2-(naphthalen-2-yloxy)-ethylsulfanyl]-benzoimidazol-1-yl}-acetic acid;
• {2-[2-(4-methoxy-phenoxy)-ethylsulfanyl]-benzoimidazol-1-yl}-acetic acid;
• {2-[2-(4-butoxy-phenoxy)-ethylsulfanyl]-benzoimidazol-1-yl}-acetic acid;
• {2-[2-(4-methylphenoxy)-ethylsulfanyl]-benzoimidazol-1-yl}-acetic acid;
• [2-(2-phenoxy-ethylsulfanyl)-benzoimidazol-1-yl]-acetic acid;
• {2-[2-(4-ethyl-phenoxy)-ethylsulfanyl]-benzoimidazol-1-yl}-acetic acid;
• {2-[2-(2-methylphenoxy)-ethylsulfanyl]-benzoimidazol-1-yl}-acetic acid;
• {2-[2-(4-chloro-phenoxy)-ethylsulfanyl]-benzoimidazol-1-yl}-acetic acid;
• {2-[2-(2-isopropyl-4-methyl-phenoxy)-ethylsulfanyl]-benzoimidazol-1-yl}-acetic acid;
• {2-[2-(naphthalen-1-yloxy)-ethylsulfanyl]-benzoimidazol-1-yl}-acetic acid;
• {2-[2-(2,6-Dimethyl-phenoxy)-ethylsulfanyl]-benzoimidazol-1-yl}-acetic acid;
• {2-[2-(4-isopropoxy-phenoxy)-ethylsulfanyl]-benzoimidazol-1-yl}-acetic acid;
• {2-[2-(2-fluoro-phenoxy)-ethylsulfanyl]-benzoimidazol-1-yl}-acetic acid;
• {2-[2-(2-methoxy-phenoxy)-ethylsulfanyl]-benzoimidazol-1-yl}-acetic acid;
• and
• {2-[3-methyl-4-(2-morpholin-4-yl-ethylsulfanyl)-pyridin-2-ylmethylsulfanyl]benzoimidazol-1-yl}-acetic acid.