IP Library › Granted Patent US 8,916,599

Granted Patent B2

US 8,916,599 · App. 13/119,834 · Granted Dec 23, 2014

1H-benz imidazole-5-carboxamides as anti-inflammatory agents

Inventors: Roland Pfau (Biberach, DE); Kirsten Arndt (Ravensburg, DE); Henri Doods (Warthausen, NL); Norbert Hauel (Schemmerhofen, DE); Klaus Klinder (Oggelshausen, DE); Raimund Kuelzer (Mittelbiberach, DE); Juergen Mack (Biberach, DE); Henning Priepke (Warthausen, DE); Dirk Stenkamp (Biberach, DE)

Assignee: Orexo AB

C07D235/30 C07D417/12 C07D401/14 C07D263/58 C07D401/12 C07D405/12 C07D413/12 C07D403/12 C07D471/04 C07D277/82

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Quick Facts

Patent No.: US 8,916,599
App. No.: 13/119,834
Granted: Dec 23, 2014
Kind: B2

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Abstract

There are provided compounds of formula (I), wherein R 1 , R 6 , R 8 , Q 2 , Q 3 , Q 3a , Q 4 , L and A have meanings given in the description, and pharmaceutically-acceptable salts thereof, which compounds are useful in the treatment of diseases in which inhibition of the activity of a member of the MAPEG family is desired and/or required, and particularly in the treatment of inflammation and/or cancer.

Claims (837)

1. A compound of formula Ib,

in which

R 1 and R 2 independently represent chloro, bromo, fluoro, C 1-3 alkyl (which latter alkyl group is optionally substituted by one or more fluoro-atoms);

R 3 , R 3a and R 4 :

independently represent hydrogen, chloro, bromo, fluoro, C 1-3 -alkyl (which latter alkyl group is optionally substituted by one or more fluoro atoms);

R 6 represents hydrogen or C 1-4 alkyl optionally substituted by one or more fluoro atoms;

R 8 represent hydrogen, fluoro, chloro, —O—C 1-4 alkyl (optionally substituted by one or more fluoro atoms);

A represents phenyl, C 3-10 cycloalkyl, C 1-12 linear or branched alkyl, all of which are optionally substituted by one or more substituents selected from R 9 ;

R 9 represents, on each occasion when used herein:

halo, —OR y10 ; C 1-7 alkyl, cycloalkyl, (which latter two groups are optionally substituted by one or more substituents selected from fluoro, —OR y10 ;

R y10 represents hydrogen or C 1-4 alkyl optionally substituted by one or more halo atoms or —OC 1-2 alkyl groups;

or a pharmaceutically acceptable salt thereof.

2. A compound according to claim 1 , which is selected from the following compounds or a pharmaceutically acceptable salt thereof:

Compound

Number

Compound Name

2-(2,6-Dichloro-phenylamino)-1H-benzimidazole-5-carboxylic acid

phenyl-amide;

2-(2,6-Dichloro-phenylamino)-1H-benzimidazole-5-carboxylic acid o-

tolylamide;

2-(2,6-Dichloro-phenylamino)-1H-benzimidazole-5-carboxylic acid m-

tolylamide;

2-(2,6-Dichloro-phenylamino)-1H-benzimidazole-5-carboxylic acid p-

tolylamide;

2-(2-Trifluoromethyl-phenylamino)-1H-benzimidazole-5-carboxylic acid-

phenyl-amide;

2-(2,5-Dichloro-phenylamino)-1H-benzimidazole-5-carboxylic acid-

phenylamide;

2-(2-Chloro-phenylamino)-1H-benzimidazole-5-carboxylic acid-

phenylamide;

2-(o-Tolyl-amino)-1H-benzimidazole-5-carboxylic acid-phenylamide;

2-(2-Methoxy-phenylamino)-1H-benzimidazole-5-carboxylic acid-

phenylamide;

2-(2-Chloro-6-methyl-phenylamino)-1H-benzimidazole-5-carboxylic

acid-phenylamide;

2-(2,6-Dimethyl-phenylamino)-1H-benzimidazole-5-carboxylic acid-

phenylamide;

2-(2-Chloro-6-fluoro-phenylamino)-1H-benzimidazole-5-carboxylic acid-

phenylamide;

2-(2,6-Dichloro-phenylamino)-1-methyl-1H-benzimidazole-5-carboxylic

acid phenylamide;

2-(2,6-Dichloro-phenylamino)-1H-benzimidazole-5-carboxylic acid (3-

cyano-phenyl)-amide;

2-(2,6-Dichloro-phenylamino)-7-methyl-1H-benzimidazole-5-carboxylic

acid (4-bromo-phenyl)-amide;

2-(2,6-Dichloro-phenylamino)-7-methyl-1H-benzimidazole-5-carboxylic

acid (4-chloro-3-fluoro-phenyl)-amide;

2-(2,6-Dichloro-phenylamino)-6-chloro-1H-benzimidazole-5-carboxylic

acid (4-bromo-phenyl)-amide;

2-(2,6-Dichloro-phenylamino)-6-chloro-1H-benzimidazole-5-carboxylic

acid (4-bromo-3-fluoro-phenyl)-amide;

2-(2,6-Dichloro-phenylamino)-6-chloro-1H-benzimidazole-5-carboxylic

acid (4-chloro-3-fluoro-phenyl)-amide;

2-(2,6-Dichloro-phenylamino)-6-chloro-1H-benzimidazole-5-carboxylic

acid (3-chloro-phenyl)-amide;

2-(2,6-Dichloro-phenylamino)-6-chloro-1H-benzimidazole-5-carboxylic

acid (4-iodo-phenyl)-amide;

2-(2,6-Dichloro-phenylamino)-1H-benzimidazole-5-carboxylic acid (4,4-

dimethyl-cyclohexyl)-amide;

2-(2,6-Dichloro-phenylamino)-1H-benzimidazole-5-carboxylic acid (4-

bromo-phenyl)-amide;

2-(2,6-Dichloro-phenylamino)-1H-benzimidazole-5-carboxylic acid (4-

chloro-3-fluoro-phenyl)-amide;

2-(2,6-Dichloro-phenylamino)-1H-benzimidazole-5-carboxylic acid (4-

bromo-3-fluoro-phenyl)-amide;

2-(2,6-Dichloro-phenylamino)-1H-benzimidazole-5-carboxylic acid (3-

bromo-phenyl)-amide;

2-(2,6-Dichloro-phenylamino)-1H-benzimidazole-5-carboxylic acid (3-

bromo-4-fluoro-phenyl)-amide;

2-(2,6-Dichloro-phenylamino)-1H-benzimidazole-5-carboxylic acid (3-

chloro-4-fluoro-phenyl)-amide;

2-(2,6-Dichloro-phenylamino)-1H-benzimidazole-5-carboxylic acid (4-

iodo-phenyl)-amide;

106

2-(2-Trifluoromethoxy-phenylamino)-1H-benzimidazole-5-carboxylic

acid (4-bromo-phenyl)-amide;

107

2-(2,4,6-Trichloro-phenylamino)-1H-benzimidazole-5-carboxylic acid (4-

bromo-phenyl)-amide;

108

2-(2,3-Dichloro-phenylamino)-1H-benzimidazole-5-carboxylic acid (4-

bromo-phenyl)-amide;

109

2-(2,4-Dichloro-phenylamino)-1H-benzimidazole-5-carboxylic acid (4-

bromo-phenyl)-amide;

110

2-(2,6-Dichloro-phenylamino)-1H-benzimidazole-5-carboxylic acid (5-

chloro-2-methyl-phenyl)-amide

111

2-(2,6-Dichloro-phenylamino)-1H-benzimidazole-5-carboxylic acid (3,4-

dichloro-phenyl)-amide;

112

2-(2,6-Dichloro-phenylamino)-1H-benzimidazole-5-carboxylic acid (3,5-

dichloro-phenyl)-amide;

113

2-(2,6-Dichloro-phenylamino)-1H-benzimidazole-5-carboxylic acid (2-

trifluoromethyl-phenyl)-amide;

114

2-(2,6-Diethyl-phenylamino)-1H-benzimidazole-5-carboxylic acid (4-

bromophenyl)-amide;

121

2-(2,6-Dichloro-phenylamino)-6-fluoro-1H-benzimidazol-5-carboxylic

acid (4-bromo-3-fluoro-phenyl)-amide;

122

2-(2,6-Dichloro-phenylamino)-6-methyl-1H-benzimidazol-5-carboxylic

acid (4-tert.-butyl-phenyl)-amide;

123

2-(2,6-Dichloro-phenylamino)-6-methyl-1H-benzimidazol-5-carboxylic

acid (4,4-dimethyl-cyclohexyl)-amide;

124

2-(2,6-Dichloro-phenylamino)-6-fluoro-1H-benzimidazol-5-carboxylic

acid (4-chloro-3-fluoro-phenyl)-amide;

135

2-(2,6-Dichloro-phenylamino)-6-methoxy-1-methyl-1H-benzimidazole-

5-carboxylic acid cyclohexylamide;

137

2-(2,6-Dichloro-phenylamino)-3H-benzimidazole-5-carboxylic acid

cyclohexylamide;

140

2-(2,6-Dichloro-phenylamino)-1H-benzimidazole-5-carboxylic acid (2,2-

dimethyl-propyl)-amide;

141

2-(2,6-Dichloro-phenylamino)-3H-benzimidazole-5-carboxylic acid

propylamide;

143

2-(2,6-Dichloro-phenylamino)-6-fluoro-3H-benzimidazole-5-carboxylic

acid (3-chloro-phenyl)-amide;

144

2-(2,6-Dichloro-phenylamino)-6-fluoro-3H-benzimidazole-5-carboxylic

acid (4-bromo-phenyl)-amide;

145

2-(2,6-Dichloro-phenylamino)-6-methyl-1H-benzimidazole-5-carboxylic

acid (4-chloro-3-fluorophenyl)-amide;

147

2-(2,6-Dichloro-phenylamino)-3H-benzimidazole-5-carboxylic acid (4,4-

difluoro-cyclohexyl)-amide;

148

2-(2,6-Dichloro-phenylamino)-6-methyl-1H-benzimidazole-5-carboxylic

acid (4-tert.-butyl-cyclohexyl)-amide;

149

2-(2,6-Dichloro-phenylamino)-6-fluoro-3H-benzimidazole-5-carboxylic

acid (4,4-difluoro-cyclohexyl)-amide;

155

2-(2,6-Dichloro-phenylamino)-6-fluoro-1H-benzimidazole-5-carboxylic

acid (trans-4-trifluoromethyl-cyclohexyl)-amide;

156

2-(2,6-Dichloro-phenylamino)-6-fluoro-1-methyl-1H-benzimidazole-5-

carboxylic acid (4,4-difluoro-cyclohexyl)-amide;

157

2-(2,6-Dichloro-phenylamino)-6-fluoro-1-methyl-1H-benzimidazole-5-

carboxylic acid (4,4-dimethyl-cyclohexyl)-amide;

158

2-(2,6-Dichloro-phenylamino)-6-fluoro-1-methyl-1H-benzimidazole-5-

carboxylic acid (trans-4-trifluoromethyl-cyclohexyl)-amide;

159

2-(2,6-Dichloro-phenylamino)-6-fluoro-1-methyl-1H-benzimidazole-5-

carboxylic acid cyclohexylamide;

161

2-(2,6-Dichloro-phenylamino)-1H-benzimidazole-5-carboxylic acid

(trans-4-trifluoromethyl-cyclohexyl)-amide;

164

2-(2,6-Dichloro-phenylamino)-6-fluoro-1-methyl-1H-benzimidazole-5-

carboxylic acid (1-methyl-cyclohexyl)-amide;

166

2-(2,6-Dichloro-phenylamino)-6-fluoro-1-methyl-1H-benzimidazole-5-

carboxylic acid octylamide;

167

2-(2,6-Dichloro-phenylamino)-6-fluoro-1-methyl-1H-benzimidazole-5-

carboxylic acid (4-bromo-phenyl)-amide;

168

2-(2,6-Dichloro-phenylamino)-1H-benzimidazole-5-carboxylic acid (cis-

4-trifluoromethyl-cyclohexyl)-amide;

169

2-(2,6-Dichloro-phenylamino)-6-fluoro-1H-benzimidazole-5-carboxylic

acid (cis-4-trifluoromethyl-cyclohexyl)-amide;

170

2-(2,6-Dichloro-phenylamino)-6-fluoro-1-methyl-1H-benzimidazole-5-

carboxylic acid (cis-4-trifluoromethyl-cyclohexyl)-amide;

171

2-(2,6-Difluoro-phenylamino)-1-methyl-1H-benzimidazole-5-carboxylic

acid (trans-4-trifluoromethyl-cyclohexyl)-amide;

172

2-(2,6-Difluoro-phenylamino)-1-methyl-1H-benzimidazole-5-carboxylic

acid (4,4-dimethyl-cyclohexyl)-amide;

173

2-(2,6-Difluoro-phenylamino)-1-methyl-1H-benzimidazole-5-carboxylic

acid (4-bromo-phenyl)-amide;

175

2-(2,6-Dichloro-phenylamino)-6-fluoro-1-methyl-1H-benzimidazole-5-

carboxylic acid ((3R)-3-methyl-cyclopentyl)-amide;

180

2-(2,6-Dichloro-phenylamino)-1-(2-methoxy-ethyl)-1H-benzimidazole-5-

carboxylic acid (4,4-dimethyl-cyclohexyl)-amide;

181

2-(2,6-Dichloro-phenylamino)-1-(2-methoxy-ethyl)-1H-benzimidazole-5-

carboxylic acid (3-chloro-phenyl)-amide;

199

2-(2,6-Dichloro-phenylamino)-6-methoxy-3H-benzimidazole-5-

carboxylic acid cyclohexylamide;

200

2-(2,6-Dichloro-phenylamino)-6-methoxy-3H-benzimidazole-5-

carboxylic acid 2-trifluoromethyl-benzylamide;

213

2-(2,6-Dichloro-phenylamino)-1H-benzimidazole-5-carboxylic acid

cyclohexyl-amide;

214

2-(2,6-Dichloro-phenylamino)-1H-benzimidazole-5-carboxylic acid

cycloheptylamide;

215

2-(2,6-Dichloro-phenylamino)-1H-benzimidazole-5-carboxylic acid (4-

methyl-cyclohexyl)-amide;

216

2-(2,6-Dichloro-phenylamino)-1H-benzimidazole-5-carboxylic acid

((1R,4R)-4-methoxy-cyclohexyl)-amide;

218

2-(2,6-Dichloro-phenylamino)-1H-benzimidazole-5-carboxylic acid

(3,3,5-trimethyl-cyclohexyl)-amide;

219

2-(2,6-Dichloro-phenylamino)-1H-benzimidazole-5-carboxylic acid

cyclopentylmethyl-amide;

224

2-(2,6-Dichloro-phenylamino)-1H-benzimidazole-5-carboxylic acid (3-

methanesulfonyl-phenyl)-amide;

225

2-(2,6-Dichloro-phenylamino)-1H-benzimidazole-5-carboxylic acid (4,4-

difluoro-cyclohexyl)-amide;

226

2-(2,6-Dichloro-phenylamino)-1H-benzimidazole-5-carboxylic acid (3-

hydroxy-cyclohexyl)-amide;

228

2-(2,6-Dichloro-phenylamino)-1H-benzimidazole-5-carboxylic acid (2-

trifluoromethyl-cyclohexyl)-amide;

229

2-(2,6-Dichloro-phenylamino)-1H-benzimidazole-5-carboxylic acid (3-

trifluoromethyl-cyclohexyl)-amide;

230

2-(2,6-Dichloro-phenylamino)-1H-benzimidazole-5-carboxylic acid (4-

trifluoromethyl-cyclohexyl)-amide;

231

2-(2,6-Dichloro-phenylamino)-1H-benzimidazole-5-carboxylic acid (1-

cyano-cyclohexyl)-amide;

237

2-(2,6-Dichloro-phenylamino)-1-methyl-1H-benzimidazole-5-carboxylic

acid (2-hydroxy-cyclohexyl)-amide;

238

2-(2,6-Dichloro-phenylamino)-1-methyl-1H-benzimidazole-5-carboxylic

acid cycloheptylamide;

239

2-(2,6-Dichloro-phenylamino)-1-methyl-1H-benzimidazole-5-carboxylic

acid (4-methyl-cyclohexyl)-amide;

240

2-(2,6-Dichloro-phenylamino)-1-methyl-1H-benzimidazole-5-carboxylic

acid (trans-4-methoxy-cyclohexyl)-amide;

241

2-(2,6-Dichloro-phenylamino)-1-methyl-1H-benzimidazole-5-carboxylic

acid (3,3,5-trimethyl-cyclohexyl)-amide;

243

2-(2,6-Dichloro-phenylamino)-1-methyl-1H-benzimidazole-5-carboxylic

acid cyclopentylmethyl-amide;

249

2-(2,6-Dichloro-phenylamino)-1-methyl-1H-benzimidazole-5-carboxylic

acid (4,4-difluoro-cyclohexyl)-amide;

253

2-(2,6-Dichloro-phenylamino)-1-methyl-1H-benzimidazole-5-carboxylic

acid (1-methyl-cyclohexyl)-amide;

254

2-(2,6-Dichloro-phenylamino)-1-methyl-1H-benzimidazole-5-carboxylic

acid (2-trifluoromethyl-cyclohexyl)-amide;

255

2-(2,6-Dichloro-phenylamino)-1-methyl-1H-benzimidazole-5-carboxylic

acid (3-trifluoromethyl-cyclohexyl)-amide;

256

2-(2,6-Dichloro-phenylamino)-1-methyl-1H-benzimidazole-5-carboxylic

acid (4-trifluoromethyl-cyclohexyl)-amide;

279

2-(2-Bromo-phenylamino)-1H-benzimidazole-5-carboxylic acid (4-

bromo-phenyl)-amide;

280

N-(3-Chloro-2-methylphenyl)-2-(2,6-dichlorophenylamino)-1H-

benzimidazole-5-carboxamide;

281

2-(2,6-Dichloro-phenylamino)-1H-benzimidazole-5-carboxylic acid (2,5-

dichloro-phenyl)-amide;

282

2-(2,6-Dichloro-phenylamino)-1H-benzimidazole-5-carboxylic acid (4-

chloro-3-trifluoromethyl-phenyl)-amide;

283

2-(2,6-Dichloro-phenylamino)-1H-benzimidazole-5-carboxylic acid (3-

trifluoromethyl-phenyl)-amide;

284

2-(2,6-Dichloro-phenylamino)-1H-benzimidazole-5-carboxylic acid (2-

chloro-phenyl)-amide;

285

2-(2,6-Dichloro-phenylamino)-1H-benzimidazole-5-carboxylic acid (3-

fluoro-phenyl)-amide;

286

2-(2,6-Dichloro-phenylamino)-1H-benzimidazole-5-carboxylic acid (3-

chloro-4-methyl-phenyl)-amide;

287

2-(2,6-Dichloro-phenylamino)-1H-benzimidazole-5-carboxylic acid

(3,4,5-trichloro-phenyl)-amide;

288

2-(2,6-Dichloro-phenylamino)-1H-benzimidazole-5-carboxylic acid

cyclohexylmethyl-amide;

291

2-(5-Chloro-2-trifluoromethoxy-phenylamino)-1H-benzimidazole-5-

carboxylic acid (4-bromo-phenyl)-amide;

292

2-(2,6-Dichloro-phenylamino)-1H-benzimidazole-5-carboxylic acid (2-

chloro-5-trifluoromethyl-phenyl)-amide;

297

2-(2,6-Dichloro-phenylamino)-1-methyl-1H-benzimidazole-5-carboxylic

acid (3-chloro-phenyl)-amide;

298

2-(2,6-Dichloro-phenylamino)-1-methyl-1-H-benzimidazole-5-carboxylic

acid (4-bromo-phenyl)-amide;

308

2-(2,6-Dichloro-phenylamino)-1-methyl-1H-benzimidazole-5-carboxylic

acid (4,4-dimethyl-cyclohexyl)-amide;

312

2-(2,6-Dichloro-phenylamino)-1H-benzimidazole-5-carboxylic acid

(2,3,4-trichloro-phenyl)-amide;

313

2-(2,6-Dichloro-phenylamino)-1H-benzimidazole-5-carboxylic acid

(2,4,6-trichloro-phenyl)-amide;

316

2-(2,6-Dichloro-phenylamino)-1-methyl-1H-benzimidazole-5-carboxylic

acid (4-bromo-phenyl)-amide;

317

2-(2,6-Dichloro-phenylamino)-1-methyl-1H-benzimidazole-5-carboxylic

acid cyclohexylamide;

318

2-(2,6-Dimethyl-phenylamino)-1-methyl-1H-benzimidazole-5-carboxylic

acid (4-bromo-phenyl)-amide;

320

1-Methyl-2-(2-trifluoromethoxy-phenylamino)-1H-benzimidazole-5-

carboxylic acid (4-bromo-phenyl)-amide;

322

2-(2,6-Dichloro-3-methyl-phenylamino)-1H-benzimidazole-5-carboxylic

acid (4-bromo-phenyl)-amide;

326

7-Bromo-2-(2,6-dichloro-phenylamino)-1-methyl-1H-benzimidazole-5-

carboxylic acid cyclohexylamide;

333

2-(3-Chloro-2-trifluoromethyl-phenylamino)-1H-benzimidazole-5-

carboxylic acid (4-bromo-phenyl)-amide;

334

2-(2-Chloro-6-fluoro-phenylamino)-1H-benzimidazole-5-carboxylic acid

(4-bromo-phenyl)-amide;

350

7-Bromo-2-(2,6-dichloro-phenylamino)-1H-benzimidazole-5-carboxylic

acid 2-trifluoromethyl-benzylamide;

351

7-Bromo-2-(2,6-dichloro-phenylamino)-1H-benzimidazole-5-carboxylic

acid (3-chloro-phenyl)-amide;

352

7-Bromo-2-(2,6-dichloro-phenylamino)-1-methyl-1H-benzimidazole-5-

carboxylic acid ethylamide;

353

7-Bromo-2-(2,6-dichloro-phenylamino)-1-methyl-1H-benzimidazole-5-

carboxylic acid isopropylamide;

354

N-(4-tert.-Butylcyclohexyl)-2-(2-chloro-6-fluorophenylamino)-6-fluoro-1-

methyl-1H-benzimidazole-5-carboxamide;

355

2-(2,6-Dichlorophenylamino)-N-(3,3-dimethylcyclohexyl)-6-fluoro-1-

methyl-1H-benzimidazole-5-carboxamide;

356

N-((1r,4r)-4-tert.-Butylcyclohexyl)-2-(2,6-dichlorophenylamino)-6-fluoro-

1H-benzimidazole-5-carboxamide;

357

N-((1r,4r)-4-tert.-Butylcyclohexyl)-2-(2-chloro-6-fluorophenylamino)-6-

fluoro-1H-benzimidazole-5-carboxamide;

358

N-(4-Bromophenyl)-2-(2-fluoro-6-trifluoromethyl-phenylamino)-1-

methyl-1H-benzimidazole-5-carboxamide;

359

N-(4-Bromophenyl)-2-(2,6-dichlorophenylamino)-6-methoxy-1-methyl-

1H-benzimidazole-5-carboxamide

362

N-(4-Ethylcyclohexyl)-2-(2-chloro-6-fluorophenylamino)-6-fluoro-1-

methyl-1H-benzimidazole-5-carboxamide;

363

2-(2-Chloro-6-fluorophenylamino-N-(4-isopropylcyclohexyl)-6-fluoro-1-

methyl-1H-benzimidazole-5-carboxamide;

368

2-(2-Chloro-6-fluorophenylamino-N-(4-isopropylcyclohexyl)-6-fluoro-1-

methyl-1H-benzimidazole-5-carboxamide;

369

2-(2,6-Dichlorophenylamino)-6-methoxy-1-methyl-N-((1r,4r)-4-

trifluoromethyl-cyclohexyl)-1H-benzimidazole-5-carboxamide;

371

N-(4-Bromophenyl)-2-(2,6-dichlorophenylamino)-6-methoxy-1H-

benzimidazole-5-carboxamide;

373

2-(2,6-Dichlorophenylamino)-6-fluoro-N-hexyl-1-methyl-1H-

benzimidazole-5-carboxamide;

374

N-((1s,4s)-4-tert.-Butylcyclohexyl)-2-(2,6-dichlorophenylamino)-6-fluoro-

1H-benzimidazole-5-carboxamide;

375

2-(2,6-Dichlorophenylamino)-6-fluoro-N-(1r,4r)-4-isopropylcyclohexyl)-

1H-benzimidazole-5-carboxamide;

376

2-(2,6-Dichlorophenylamino)-6-methoxy-N-((1r,4r)-4-trifluoromethyl-

cyclohexyl)-1H-benzimidazole-5-carboxamide;

378

N-((1s,4s)-4-tert.-Butylcyclohexyl)-2-(2-chloro-6-fluorophenylamino)-6-

fluoro-1H-benzimidazole-5-carboxamide;

380

N-(4-Bromophenyl)-2-(2,5-dichlorophenylamino)-1-methyl-1H-

benzimidazole-5-carboxamide;

381

N-(4-Bromophenyl)-2-(2-chloro-6-fluorophenylamino)-1-methyl-1H-

benzimidazole-5-carboxamide;

382

N-(4-Bromophenyl)-2-(2-chloro-6-methylphenylamino)-1-methyl-1H-

benzimidazole-5-carboxamide;

383

2-(2,6-Dichlorophenylamino)-6-methoxy-N-((3-trifluoromethyl-pyridin-2-

yl)-methyl)-1H-benzimidazole-5-carboxamide;

384

2-(2-Chloro-6-fluorophenylamino)-6-fluoro-1-methyl-N-(spiro[2.5]octan-

6-yl-1H-benzimidazole-5-carboxamide;

385

N-(4-Bromophenyl)-2-(4-fluoro-2-trifluoromethyl-phenylamino)-1-

methyl-1H-benzimidazole-5-carboxamide;

390

2-(2-Chloro-6-fluorophenylamino)-N-(3-cyclopropylpropyl)-6-fluoro-1-

methyl-1H-benzimidazole-5-carboxamide;

391

2-(2,6-Dichlorophenylamino)-6-fluoro-1-methyl-N-pentyl-1H-

benzimidazole-5-carboxamide;

392

2-(2-Chloro-6-fluorophenylamino)-N-(3-ethylcyclopentyl)-6-fluoro-1-

methyl-1H-benzimidazole-5-carboxamide;

395

N-(4-Bromophenyl)-2-(2,6-dichlorophenylamino)-4,5-difluoro-1H-

benzimidazole-6-carboxamide;

397

N-(2-Cyclobutylethyl)-2-(2,6-dichlorophenylamino)-6-fluoro-1-methyl-

1H-benzimidazole-5-carboxamide;

398

N-(3-Cyclopropylpropyl)-2-(2,6-dichlorophenylamino)-6-fluoro-1-methyl-

1H-benzimidazole-5-carboxamide;

399

2-(2-Chloro-6-fluorophenylamino)-6-fluoro-N-(spiro[2.5]octan-6-yl)-1H-

benzimidazole-5-carboxamide;

402

N-(4-Bromophenyl)-2-(2,4-dichloro-6-methylphenylamino)-1-methyl-1H-

benzimidazole-5-carboxamide;

404

2-(2-Chloro-6-fluorophenylamino)-N-(3,3-dimethylcyclohexyl)-6-fluoro-

1-methyl-1H-benzimidazole-5-carboxamide;

405

7-Bromo-N-(3-chlorophenyl)-2-(2,6-dichlorophenylamino)-1-methyl-1H-

benzimidazole-5-carboxamide;

408

2-(2,6-Dichlorophenylamino)-6-fluoro-1-methyl-N-(4-methylpentyl)-1H-

benzimidazole-5-carboxamide;

412

2-(2,6-Dichlorophenylamino)-N-(3-ethylcyclopentyl)-6-fluoro-1-methyl-

1H-benzimidazole-5-carboxamide;

415

2-(2,6-Dichlorophenylamino)-6-fluoro-1-methyl-N-(spiro[2.4]heptan-5-

yl)-1H-benzimidazole-5-carboxamide;

416

(R)-2-(2,6-Dichlorophenylamino)-6-fluoro-N-(hexan-2-yl)-1-methyl-1H-

benzimidazole-5-carboxamide;

419

2-(2,6-Dichlorophenylamino)-6-fluoro-1-methyl-N-(spiro[2.5]octan-6-yl)-

1H-benzimidazole-5-carboxamide;

420

2-(2,6-Dichloro-4-fluorophenylamino)-N-(4,4-dimethylcyclohexyl)-1-

methyl-1H-benzimidazole-5-carboxamide;

423

N-(4-Bromophenyl)-2-(2-chloro-5-trifluoromethyl-phenylamino)-1-

methyl-1H-benzimidazole-5-carboxamide;

428

2-(2,6-Dichlorophenylamino)-6-fluoro-N-isopentyl-1-methyl-1H-

benzimidazole-5-carboxamide;

430

2-(2-Chloro-6-fluorophenylamino)-N-(4,4-dimethylcyclohexyl)-6-fluoro-

1-methyl-1H-benzimidazole-5-carboxamide;

432

2-(2,6-Dichloro-4-fluorophenylamino)-1-methyl-N-((1R,4R)-4-

trifluoromethyl-cyclohexyl)-1H-benzimidazole-5-carboxamide;

433

N-(4-Bromophenyl)-2-(4-chloro-2-trifluoromethyl-phenylamino)-1-

methyl-1H-benzimidazole-5-carboxamide;

436

2-(2,6-Dichlorophenylamino)-1-methyl-N-(spiro[2.4]heptan-5-yl)-1H-

benzimidazole-5-carboxamide;

437

2-(2,6-Dichlorophenylamino)-N-(4-ethylcyclohexyl)-6-fluoro-1-methyl-

1H-benzimidazole-5-carboxamide;

441

2-(2-Chloro-6-fluorophenylamino)-1-methyl-N-(spiro[2.5]octan-6-yl)-1H-

benzimidazole-5-carboxamide;

442

2-(2,6-Dichlorophenylamino)-6-fluoro-1-methyl-N-((1R,3R)-3-

methylcyclohexyl)-1H-benzimidazole-5-carboxamide;

443

(S)-2-(2,6-Dichlorophenylamino)-6-fluoro-N-(hexan-2-yl)-1H-

benzimidazole-5-carboxamide;

447

2-(2,6-Dichlorophenylamino)-N-(3,3-dimethylcyclobutyl)-6-fluoro-1-

methyl-1H-benzimidazole-5-carboxamide;

450

(S)-2-(2,6-Dichlorophenylamino)-6-fluoro-N-(hexan-2-yl)-1-methyl-1H-

benzimidazole-5-carboxamide;

456

N-(4-Bromophenyl)-2-(2-chloro-4-fluorophenylamino)-1-methyl-1H-

benzimidazole-5-carboxamide;

457

(R)-2-(2,6-Dichlorophenylamino)-6-fluoro-N-(hexan-2-yl)-1H-

benzimidazole-5-carboxamide;

458

2-(2-Chloro-6-fluorophenylamino)-6-fluoro-N-hexyl-1-methyl-1H-

benzimidazole-5-carboxamide;

475

2-(2,6-Dichlorophenylamino)-N-((1r,4r)-4-(difluoromethyl)cyclohexyl)-6-

fluoro-1-methyl-1H-benzimidazole-5-carboxamide;

476

2-(2-Chloro-6-fluorophenylamino)-N-((1r,4r)-4-

(difluoromethyl)cyclohexyl)-6-fluoro-1-methyl-1H-benzimidazole-5-

carboxamide;

483

2-(2,6-Dichlorophenylamino)-1-methyl-N-(spiro[2.5]octan-6-yl)-1H-

benzimidazole-5-carboxamide;

484

N-(2-Cyclopropylethyl)-2-(2,6-dichlorophenylamino)-6-fluoro-1-methyl-

1H-benzimidazole-5-carboxamide;

488

2-(2-Chloro-6-fluorophenylamino)-N-(spiro[2.5]octan-6-yl)-1H-

benzimidazole-5-carboxamide;

489

N-(4-Bromophenyl)-2-(2-chloro-4,6-dimethylphenylamino)-1-methyl-1H-

benzimidazole-5-carboxamide;

496

2-(2,6-Dichlorophenylamino)-N-((1r,4r)-4-(difluoromethyl)cyclohexyl)-6-

fluoro-1H-benzimidazole-5-carboxamide;

499

N-(4-Bromophenyl)-2-(2-chloro-6-(dimethylamino)phenylamino)-1-

methyl-1H-benzimidazole-5-carboxamide;

501

2-(2-Chloro-6-fluorophenylamino)-6-fluoro-1-methyl-N-((3R)-3-

methylcyclopentyl)-1H-benzimidazole-5-carboxamide;

502

2-(2-Chloro-6-fluorophenylamino)-N-(2-cyclopropylethyl)-6-fluoro-1-

methyl-1H-benzimidazole-5-carboxamide;

512

N-(4-Bromophenyl)-2-(2-chloro-4-methylphenylamino)-1-methyl-1H-

benzimidazole-5-carboxamide;

514

7-Bromo-N-cyclohexyl-2-(2,6-dichlorophenylamino)-1H-benzimidazole-

5-carboxamide;

516

N-(Cyclobutylmethyl)-2-(2,6-dichlorophenylamino)-6-fluoro-1-methyl-

1H-benzimidazole-5-carboxamide;

519

N-(4-Bromophenyl)-2-(2,4-dichlorophenylamino)-1-methyl-1H-

benzimidazole-5-carboxamide;

526

N-(4-Bromophenyl)-2-(2-chloro-5-(methylsulfonyl)phenylamino)-1-

methyl-1H-benzimidazole-5-carboxamide;

537

N-(4-Bromophenyl)-2-(5-carbamoyl-2-chlorophenylamino)-1-methyl-1H-

benzimidazole-5-carboxamide;

540

N-(4-Bromophenyl)-2-(2-chloro-4-(methylcarbamoyl)-phenylamino)-1-

methyl-1H-benzimidazole-5-carboxamide;

546

2-(2-Chloro-6-fluorophenylamino)-N-(cyclopropylmethyl)-6-fluoro-1-

methyl-1H-benzimidazole-5-carboxamide;

551

N-(4-Bromophenyl)-2-(2-dimethylamino-6-fluorophenylamino)-1-methyl-

1H-benzimidazole-5-carboxamide;

556

N-(4-Bromophenyl)-2-(2-chloro-4-trifluoromethyl-phenylamino)-1-

methyl-1H-benzimidazole-5-carboxamide;

557

N-(4-Bromophenyl)-2-(2-chloro-6-(trifluoromethoxy)phenylamino)-1H-

benzimidazole-5-carboxamide;

562

N-(4-Bromophenyl)-2-(2-chloro-4-(dimethylcarbamoyl)-phenylamino)-1-

methyl-1H-benzimidazole-5-carboxamide;

570

7-Bromo-N-isopropyl-2-(2,6-dichlorophenylamino)-1H-benzimidazole-5-

carboxamide;

572

N-(4-Bromophenyl)-2-(2-isopropylphenylamino)-1-methyl-1H-

benzimidazole-5-carboxamide;

573

3-(5-(4-Bromophenylcarbamoyl)-1-methyl-1H-benzimidazol-2-yl-

amino)-4-chlorobenzoic acid; or

574

N-(4-Bromophenyl)-2-(2-chloro-5-(methylcarbamoyl)-phenylamino)-1-

methyl-1H-benzimidazole-5-carboxamide.

3. A compound according to claim 1 , which is selected from the following compounds or a pharmaceutically acceptable salt thereof:

Compound

Number

Compound Name

578

2-(2,6-Dichloro-4-fluoro-phenylamino)-N-(4-bromo-phenyl)-1-methyl-1H-

benzimidazole-5-carboxamide

579

2-(2,6-Dichloro-4-fluoro-phenylamino)-6-methoxy-N-(trans-4-

trifluoromethyl-cyclohex-1-yl)-1H-benzimidazole-5-carboxamide

581

2-(2,6-Dichloro-4-fluoro-phenylamino)-6-methoxy-N-(4-bromo-phenyl)-

1H-benzimidazole-5-carboxamide

582

2-(2,6-Dichloro-4-fluoro-phenylamino)-N-(4-bromo-phenyl)-6-(2,2,2-

trifluorethoxy)-1H-benzimidazole-5-carboxamide

583

2-(2,6-Dichloro-4-fluoro-phenylamino)-N-(trans-4-trifluoromethyl-

cyclohex-1-yl)-6-(2,2,2-trifluoroethoxy)-1H-benzimidazole-5-carboxamide

584

2-(2,6-Dichloro-4-fluoro-phenylamino)-N-(trans-4-trifluoro-cyclohex-1-yl)-

6-(2-fluoroethoxy)-1H-benzimidazole-5-carboxamide

585

2-(2,6-Dichloro-4-fluoro-phenylamino)-N-(4-bromo-phenyl)-6-(2-

fluoroethoxy)-1H-benzimidazole-5-carboxamide

586

2-(2,6-Dichloro-4-fluoro-phenylamino)-N-(4-bromo-phenyl)-6-(2,2-

difluoroethoxy)-1H-benzimidazole-5-carboxamide

587

2-(2,6-Dichloro-4-fluoro-phenylamino)-N-(trans-4-trifluoromethyl-

cyclohex-1-yl)-6-(2,2-difluoroethoxy)-1H-benzimidazole-5-carboxamide

588

N-(4-Bromo-phenyl)-2-(2,3-dichloro-6-fluoro-phenylamino)-6-(2,2,2-

trifluoroethoxy)-1H-benzimidazole-5-carboxamide

589

2-(2,6-Dichloro-phenylamino)-6-(2,2,2-trifluoroethoxy)-N-(trans-4-

trifluoromethyl-cyclohex-1-yl)-1H-benzimidazole-5-carboxamide

590

2-(2,6-Dichloro-phenylamino)-N-(4-bromo-phenyl)-6-(2,2,2-

trifluoroethoxy)-1H-benzimidazole-5-carboxamide

591

2-(2,3-Dichloro-6-fluoro-phenylamino)-6-(2,2,2-trifluoro-ethoxy)-N-(4-trans-

trifluoromethyl-cyclohex-1-yl) 1H-benzimidazole-5-carboxamide

592

2-(3,6-Dichloro-2-fluoro-phenylamino)-N-(4-trans-trifluoromethyl-

cyclohex-1-yl)-6-(2,2,2-trifluorethoxy)-1H-benzimidazole-5-carboxamide

593

2-(3,6-Dichloro-2-fluoro-phenylamino)-N-(4-bromophenyl)-6-(2,2,2-

trifluorethoxy)-1H-benzimidazole-5-carboxamide

594

2-(2-Chloro-3,6-difluoro-phenylamino)-N-(4-trans-trifluoromethyl-

cyclohex-1-yl)-6-(2,2,2-trifluorethoxy)-1H-benzimidazole-5-carboxamide

595

2-(2-Chloro-3,6-difluoro-phenylamino)-N-(4-bromophenyl)-6-(2,2,2-

trifluorethoxy)-1H-benzimidazole-5-carboxamide

596

2-(3,6-Dichloro-2-fluoro-phenylamino)-N-(4,4-dimethyl-cyclohex-1-yl)-6-

fluoro-1H-benzimidazole-5-carboxamide

597

2-(3,6-Dichloro-2-fluoro-phenylamino)-N-(trans-4-trifluoromethyl-

cyclohex-1-yl)-6-fluoro-1H-benzimidazole-5-carboxamide

598

2-(3,6-Dichloro-2-fluoro-phenylamino)-N-(3-chlorphenyl)-6-fluoro-1H-

benzimidazole-5-carboxamide

599

2-(3,6-Dichloro-2-fluoro-phenylamino)-6-ethoxy-N-(trans-4-

trifluoromethyl-cyclohex-1-yl)-1H-benzimidazole-5-carboxamide

600

2-(3,6-Dichloro-2-fluoro-phenylamino)-N-(4,4-dimethyl-cyclohexyl)-6-

ethoxy-1H-benzimidazole-5-carboxamide

601

2-(3,6-Dichloro-2-fluoro-phenylamino)-6-fluoro-N-(trans-4-trifluoromethyl-

cyclohex-1-yl)-1 -methyl-1H-benzimidazole-5-carboxamide

602

2-(3,6-Dichloro-2-fluoro-phenylamino)-6-methoxy-N-(4-bromophenyl)-

1H-benzimidazole-5-carboxamide

603

2-(3,6-Dichloro-2-fluoro-phenylamino)-N-(3-chloro-phenyl)-6-ethoxy-1H-

benzimidazole-5-carboxamide

604

2-(3,6-Dichloro-2-fluoro-phenylamino)-N-(4-bromo-phenyl)-6-ethoxy-1H-

benzimidazole-5-carboxamide

605

2-(3,6-Dichloro-2-fluoro-phenylamino)-6-ethoxy-N-(4-trans-

trifluoromethyl-cyclohex-1-yl)-1-methyl-1H-benzimidazole-5-carboxamide

606

2-(3,6-Dichloro-2-fluoro-phenylamino)-6-fluoro-N-(spiro[2.5]oct-6-yl)-1-

methyl-1H-benzimidazole-5-carboxamide

607

2-(3,6-Dichloro-2-fluoro-phenylamino)-6-ethoxy-N-(4,4-dimethyl-

cyclohex-1-yl)-1-methyl-1H-benzimidazole-5-carboxamide

608

2-(3,6-Dichloro-2-fluoro-phenylamino)-N-(spiro[2.5]oct-6-yl)-6-fluoro-1H-

benzimidazole-5-carboxamide

609

2-(3,6-Dichloro-2-fluoro-phenylamino)-6-ethoxy-N-(spiro[2.5]oct-6-yl)-1-

methyl-1H-benzimidazole-5-carboxamide

610

2-(3,6-Dichloro-2-fluoro-phenylamino)-N-(4-bromo-phenyl)-6-

isopropoxy-1H-benzimidazole-5-carboxamide

611

2-(3,6-Dichloro-2-fluoro-phenylamino)-6-isopropoxy-N-cyclohexyl-1H-

benzimidazole-5-carboxamide

612

2-(3,6-Dichloro-2-fluoro-phenylamino)-N-cyclohexyl-6-methoxy-1H-

benzimidazole-5-carboxamide

613

2-(3,6-Dichloro-2-fluoro-phenylamino)-N-(spiro[2.5]oct-6-yl)-6-methoxy-

1H-benzimidazole-5-carboxamide

614

2-(3,6-Dichloro-2-fluoro-phenylamino)-N-(3-chloro-phenyl)-6-

isopropoxy-1H-benzimidazole-5-carboxamide

615

2-(3,6-Dichloro-2-fluoro-phenylamino)-6-isopropoxy-N-(spiro[2.5]oct-6-

yl)-1H-benzimidazole-5-carboxamide

616

2-(3,6-Dichloro-2-fluoro-phenylamino)-N-(4,4-dimethyl-cyclohex-1-yl)-6-

methoxy-1H-benzimidazole-5-carboxamide

617

2-(3,6-Dichloro-2-fluoro-phenylamino)-6-methoxy-N-(4-trans-

trifluoromethyl-cyclohex-1-yl)-1H-benzimidazole-5-carboxamide

618

2-(3,6-Dichloro-2-fluoro-phenylamino)-6-isopropoxy-N-(4,4-dimethyl-

cyclohex-1-yl)-1H-benzimidazole-5-carboxamide

619

2-(3,6-Dichloro-2-fluoro-phenylamino)-6-methoxy-N-cyclohexyl-1-

methyl-1H-benzimidazole-5-carboxamide

620

2-(3,6-Dichloro-2-fluoro-phenylamino)-6-isopropoxy-N-(4-trans-

trifluoromethyl-cyclohex-1-yl)-1H-benzimidazole-5-carboxamide

621

2-(3,6-Dichloro-2-fluoro-phenylamino)-6-methoxy-N-(4,4-dimethyl-

cyclohex-1-yl)-1-methyl-1H-benzimidazole-5-carboxamide

622

2-(6-Chloro-2-fluoro-3-methyl-phenylamino)-6-methoxy-N-(4-trans-

trifluoromethyl-cyclohex-1-yl)-1H-benzimidazole-5-carboxamide

623

2-(6-Chloro-2-fluoro-3-methyl-phenylamino)-6-fluoro-N-cyclohexyl-1-

methyl-1H-benzimidazole-5-carboxamide

624

2-(3,6-Dichloro-2-fluoro-phenylamino)-6-isopropoxy-N-cyclohexyl-1-

methyl-1H-benzimidazole-5-carboxamide

625

2-(3,6-Dichloro-2-fluoro-phenylamino)-6-isopropoxy-N-(4,4-dimethyl-

cyclohex-1-yl)-1-methyl-1 H-benzimidazole-5-carboxamide

626

2-(6-Chloro-2-fluoro-3-methyl-phenylamino)-6-methoxy-N-(4,4-dimethyl-

cyclohex-1-yl-1H-benzimidazole-5-carboxamide

627

2-(6-Chloro-2-fluoro-3-methyl-phenylamino)-6-fluoro-N-(4,4-dimethyl-

cyclohex-1-yl)-1-methyl-1H-benzimidazole-5-carboxamide

628

2-(6-Chloro-2-fluoro-3-methyl-phenylamino)-6-methoxy-N-cyclohexyl-

1H-benzimidazole-5-carboxamide

629

2-(6-Chloro-2-fluoro-3-methyl-phenylamino)-6-fluoro-N-(trans-4-

trifluoromethyl-cyclohex-1-yl)-1-methyl-1H-benzimidazole-5-carboxamide

632

N-(2,2,3,3,4,4,4-heptafluoro-butyl)-2-(2,6-dichlorophenylamino)-6-

methoxy-1H-benzimidazole-5-carboxamide

639

2-(2,6-Dichloro-3-cyanomethyl-phenylamino)-N-(4-bromphenyl)-6-

methoxy-1H-benzimidazol-5-carboxamide

640

2-(2,5-Di-(trifluoromethyl)-phenylamino)-N-(4-bromphenyl)-6-methoxy-1-

methyl-1H-benzimidazol-5-carboxamide

641

2-(5-Methyl-2-trifluoromethyl-phenylamino)-N-(4-bromphenyl)-6-

methoxy-1-methyl-1H-benzimidazol-5-carboxamide

642

2-(5-Fluoro-2-trifluoromethyl-phenylamino)-N-(4-bromphenyl)-6-

methoxy-1-methyl-1H-benzimidazol-5-carboxamide

643

2-(3,6-Dichloro-2-fluoro-phenylamino)-6-methoxy-N-(trans-4-

trifluoromethyl-cyclohex-1-yl)-1-methyl-1H-benzimidazole-5-carboxamide

644

2-(3,6-Dichloro-2-fluoro-phenylamino)-6-isopropoxy-N-(4-trans-

trifluoromethyl-cyclohex-1-yl)-1-methyl-1H-benzimidazole-5-carboxamide

645

2-(3,6-Dichloro-2-fluoro-phenylamino)-6-methoxy-N-(spiro[2.5]oct-6-yl)-

1-methyl-1H-benzimidazole-5-carboxamide

646

2-(3,6-Dichloro-2-fluoro-phenylamino)-6-ethoxy-N-(spiro[2.5]oct-6-yl)-

1H-benzimidazole-5-carboxamide

647

2-(6-Chloro-2-fluoro-3-methyl-phenylamino)-6-methoxy-N-(trans-4-

trifluoromethyl-cyclohex-1-yl)-1-methyl-1H-benzimidazole-5-carboxamide

648

2-(3,6-Dichloro-2-fluoro-phenylamino)-6-isopropoxy-N-(spiro[2.5]oct-6-

yl)-1-methyl-1H-benzimidazole-5-carboxamide

649

2-(6-Chloro-2-fluoro-3-methyl-phenylamino)-N-cyclohexyl-6-fluoro-1H-

benzimidazole-5-carboxamide

650

2-(6-Chloro-2-fluoro-3-methyl-phenylamino)-6-methoxy-N-(4,4-dimethyl-

cyclohex-1-yl)-1-methyl-1H-benzimidazole-5-carboxamide

651

2-(6-Chloro-2-fluoro-3-methyl-phenylamino)-6-methoxy-N-cyclohexyl-1-

methyl-1H-benzimidazole-5-carboxamide

652

2-(2,3,5,6-tetrafluoro-phenylamino)-6-methoxy-N-(4,4-dimethyl-

cyclohex-1-yl)-1-methyl-1H-benzimidazole-5-carboxamide

653

2-(6-Chloro-2-fluoro-3-methyl-phenylamino)-N-(trans-4-trifluoromethyl-

cyclohex-1-yl)-6-fluoro-1H-benzimidazole-5-carboxamide: or

654

2-(5-Fluoro-2-trifluoromethyl-phenylamino)-N-(4-bromphenyl)-6-

methoxy-1-methyl-1H-benzimidazol-5-carboxamide.

4. A pharmaceutical formulation comprising a compound according to claim 1 , or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable adjuvant, diluent or carrier.

Assignments (2)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 20, 2014

From: BOEHRINGER INGELHEIM INTERNATIONAL GMBH

To: OREXO AB

Reel/Frame 033986/0609 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 7, 2011

From: PFAU, ROLAND; ARNDT, KIRSTEN; DOODS, HENRI; HAUEL, NORBERT; KLINDER, KLAUS; KUELZER, RAIMUND; MACK, JUERGEN; PRIEPKE, HENNING; STENKAMP, DIRK

To: BOEHRINGER INGELHEIM INTERNATIONAL GMBH

Reel/Frame 026402/0095 →

Priority Claims (1)

EP 08165120 · Sep 25, 2008 · regional

Continuity (2)

Provisional Application 61099987 · Sep 25, 2008

Related Publication 20110312935A1 · Dec 22, 2011