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1-Cyclohexyl-2-phenylaminobenzimidazoles as midh1 inhibitors for the treatment of tumors
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A C1-C6-, C1-C3- technology, applied in the field of 1-cyclohexyl-2-phenylaminobenzimidazole used as a MIDH1 inhibitor for the treatment of tumors, can solve the problem of no record of benzimidazole compounds
Inactive Publication Date: 2020-11-06
DEUTES KREBSFORSCHUNGSZENT STIFTUNG DES OFFENTLICHEN RECHTS
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[0025] However, the above prior art does not describe the specifically substituted benzimidazole compounds of the general formula (I) of the present invention as defined herein, or as described and defined herein and as hereinafter referred to as "compounds of the invention" Stereoisomers, tautomers, N-oxides, hydrates, solvates or salts thereof, or mixtures thereof, or their pharmacological activity
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Embodiment 2-1
[0610] Example 2-1 (±) 5-(3,5-dimethyl-1,2-oxazol-4-yl)-N-[4-(trifluoromethoxy)phenyl]-1-[ (cis)-3,3,5-trimethylcyclohexyl]-1H-benzimidazol-2-amine
[0611] with
[0612] 150 mg (0.30 mmol) (±) 5-bromo-N-[4-(trifluoromethoxy)phenyl]- 1-[(cis)-3,3,5-trimethylcyclohexyl]-1H-benzimidazol-2-amine (intermediate 1-1), 85.2mg (0.60mmol) (3,5-dimethyl 1,2-oxazol-4-yl)boronic acid (commercially available, CAS-RN: 16114-47-9), 24.7mg (0.03mmol) 1,1'-(bisdiphenylphosphino) Ferrocene dichloropalladium (II) and 96.1mg (0.91mmol) Na 2 CO 3 Heat in a microwave at 110°C for 60 minutes. The reaction mixture was placed on a flash column and washed with ethyl acetate (250 mL) to remove catalyst and salts. The filtrate was evaporated to dryness, and the residue was purified by column chromatography to obtain 103.1 mg (66.6%) of the title compound.
[0613] UPLC-MS:R t = 1.53 min; m / z = 513.2 (ES+, M+1).
[0615] Example 2-1-1 5-(3,5-dimethyl-1,2-oxazol-4-yl)-N-[4-(trifluoromethoxy)phenyl]-1-[( cis)-3,3,5-trimethylcyclohexyl]-1H-benzimidazol-2-amine, enantiomer A
[0616] or
Embodiment 2-1-2
[0619] Example 2-1-2 5-(3,5-dimethyl-1,2-oxazol-4-yl)-N-[4-(trifluoromethoxy)phenyl]-1-[( cis)-3,3,5-trimethylcyclohexyl]-1H-benzimidazol-2-amine, enantiomer B
[0620] or
[0621] Racemic compound (±) 5-(3,5-dimethyl-1,2-oxazol-4-yl)-N-[4-(trifluoromethoxy)phenyl]-1-[( Cis)-3,3,5-trimethylcyclohexyl]-1H-benzimidazol-2-amine (Example 2-1; 67 mg) was passed through chiral HPLC (system: Agilent Prep 1200, 2×Prep pump, DLA, MWD, Prep FC; Column: Chiralpak IA, 5 μM 250×20 mm; Injection volume: 67 mg in 4×0.5 mL acetone / DMSO; Solvent: hexane, 2-propanol, diethylamine (70:30: 0.1); flow rate: 25mL / min; detection: UV 254nm) was separated into its enantiomers to obtain 25 mg of the title compound (enantiomer B, retention time range: 10.5-13.8 minutes) and 20 mg of the enantiomer in Example 2 - Enantiomer A described in 1-1.
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Abstract
The present invention relates to benzimidazol-2-amines of general formula (I) in which R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11 and R12 are as defined herein, to methods of preparing said compounds, to intermediate compounds useful for preparing said compounds, to pharmaceutical compositions and combinations comprising said compounds and to the use of said compounds for manufacturing a pharmaceutical composition for the treatment or prophylaxis of a disease, in particular of neoplasms, as a sole agent or in combination with other active ingredients.
Description
technical field [0001] The present invention relates to benzimidazol-2-amine compounds of general formula (I) as described and defined herein, processes for the preparation of said compounds, intermediate compounds useful for the preparation of said compounds, medicaments comprising said compounds Compositions and combinations, and uses of said compounds as sole agents or in combination with other active ingredients for the manufacture of pharmaceutical compositions for the treatment or prevention of diseases, especially tumors. Background technique [0002] The present invention relates to compounds inhibiting mutated isocitrate dehydrogenase 1 (mIDH1 R132H), processes for the preparation of said compounds, pharmaceutical compositions and combinations comprising said compounds for the manufacture of Use of pharmaceutical compositions for diseases, and intermediate compounds useful for the preparation of said compounds. [0003] Isocitrate dehydrogenase (IDH) is a key enzym...
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