Patent NZ-621325-A (NZ)
Title: Cyclopropaneamine compound
Inventor: KAJII SHIGEO
IPC: C07D513/04
Filed: 2012-08-08
Abstract: Disclosed are N-(4-{ trans-2-[amino]cyclopropyl} -phenyl)benzamide analogues and derivatives as represented by the general formula (I), wherein A is a cyclic ring containing moiety as defined herein; R is a hydrogen atom or an alkyl group; or A and R are optionally bonded to each other to form a dihydroisoindole ring having 1 or 2 oxo groups; Q1 is a hydrogen atom or an alkyl group; Q2, Q3 and Q4 are each a hydrogen atom; X is a hydrogen atom or an alkyl group optionally substituted by one cycloalkyl group; Z1, Z2 and Z3 are each a hydrogen atom; Y1, Y2 and Y3 are each independently: (1) a hydrogen atom, (2) an alkyl group optionally having 1 to 3 substituents, (3) a cycloalkyl group, (4) a phenyl group optionally having 1 to 3 substituents, (5) a pyridyl group optionally having 1 to 3 alkoxy groups, (6) a naphthyl group, (7) a biphenylyl group, (8) a thienyl group, (9) an imidazolyl group, (10) a thiazolyl group, (11) an imidazopyridyl group, (12) an imidazothiazolyl group, (13) a thienopyridyl group, or (14) a 1,8-naphthyridinyl group; or Y1 and Y2 are optionally bonded to each other to form, together with the adjacent carbon atom, a cycloalkane ring, a pyrrolidine ring, a piperidine ring, a tetrahydropyran ring, a 2,3-dihydroindene ring, a fluorene ring, a 8-azabicyclo[3.2.1]octane ring, or a tetrahydrothiopyran ring, each of which optionally has 1 to 3 substituents; or X and Y1 are optionally bonded to each other to form a pyrrolidine ring, together with the adjacent nitrogen atom and carbon atom; and wherein the remaining substituents are as defined herein; or a salt thereof. Also disclosed are the compounds N-(4-{ trans-2-[(cyclopropylmethyl)amino]cyclopropyl} phenyl)biphenyl-4-carboxamide, N-(4-{ trans-2-[(1-methylpiperidin-4-yl)amino]cyclopropyl} phenyl)-3-(trifluoromethyl)benzamide, N-(4-{ trans-2-[(cyclopropylmethyl)amino]cyclopropyl} phenyl)-1H-pyrazole-4-carboxamide, N-(4-{ trans-2-[(cyclopropylmethyl)amino]cyclopropyl} -2-methylphenyl)benzamide, N-(4-{ trans-2-[(cyclopropylmethyl)amino]cyclopropyl} phenyl)-3-(trifluoromethoxy)benzamide, N-(4-{ trans-2-[(cyclopropylmethyl)amino]cyclopropyl} phenyl)benzamide, N-(4-{ trans-2-[(cyclopropylmethyl)amino]cyclopropyl} phenyl)-cyclohexanecarboxamide, N-(4-{ trans-2-[(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)amino]cyclopropyl} phenyl)-3-(trifluoromethyl)benzamide, N-(4-{ trans-2-[(cyclopropylmethyl)amino]cyclopropyl} phenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamide, N-(4-{ trans-2-[(cyclopropylmethyl)amino]cyclopropyl} phenyl)-1,5-dimethyl-1H-pyrazole-3-carboxamide, N-(4-{ trans-2-[(cyclopropylmethyl)amino]cyclopropyl} phenyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide, N-(4-{ trans-2-[(cyclopropylmethyl)amino]cyclopropyl} phenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide, and N-(4-{ trans-2-[(cyclopropylmethyl)amino]cyclopropyl} phenyl)-1-methyl-1H-pyrazole-4-carboxamide. Also disclosed is a medicament comprising the compound as defined above or a salt thereof, which is a prophylactic or therapeutic agent for cancer, and/or an LSD1 inhibitor, and/or a prophylactic or therapeutic agent for schizophrenia, Alzheimer’s disease, Parkinson’s disease or Huntington’s chorea.