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US 7,678,818 B2Granted
Anthranilamide and 2-amino-heteroarene-carboxamide compounds
AssigneeHoffmann-La Roche Inc.
InventorsAurelia Conte, Holger Kuehne, Thomas Luebbers, Patrizio Mattei, Cyrille Maugeais, Werner Mueller, Philippe Pflieger
Life of this patent
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Abstract
Compounds of formula I processes for their preparation, their use as pharmaceuticals and to pharmaceutical compositions comprising them.
Claims20
A compound of formula (I):
- or a pharmaceutically acceptable salt thereof, wherein:
- R1, R2, R4 and R5 are independently hydrogen, C1-C6alkyl, C1-C6alkoxy or halogen;
- R3 is selected from the group consisting of:
- (1) C3-C6alkyl,
- (2) halogen-C1-C6alkyl,
- (3) C3-C6cycloalkyl optionally substituted by halogen or alkoxy,
- (4) Si(C1-C6alkyl)3,
- (5) —OR12, wherein R12 is (a) C1-C6alkyl optionally substituted by halogen, hydroxy, COOC1-C6alkyl, C3-C6cycloalkyl or phenyl which phenyl is optionally substituted by halogen or cyano, (b) halogen-C1-C6alkyl, (c) C3-C6cycloalkyl, (d) phenyl, (e) benzyl optionally substituted by halogen or cyano, or (f) S(O)2-C1-C6alkyl, and
- (6) pentafluorosulfuranyl;
- or
- R2 and R3 taken together with the carbon atoms they are attached to form a 5- or 6-membered carbocyclic ring or a 5- or 6-membered heterocyclic ring containing one or two heteroatoms selected from N, O or S;
- R6 is hydrogen or C1-C6alkyl;
- R7 and R8 are independently hydrogen, C1-C6alkyl, hydroxy or halogen;
- R9 is selected from the group consisting of:
- (1) hydrogen,
- (2) C1-C6alkyl,
- (3) C2-C6alkenyl,
- (4) halogen-C1-C6alkyl,
- (5) heterocyclyl,
- (6) heteroaryl,
- (7) phenyl,
- (8) naphthyl, and
- (9) —NR14R15, wherein R14 and R15 independently are hydrogen, C1-C6alkyl or phenyl optionally substituted by halogen;
- wherein said heteroaryl or phenyl is optionally substituted by:
- (a) halogen, (b) C1-C6alkyl optionally substituted by halogen, (c) C1-C6alkoxy optionally substituted by halogen or (d) phenyl
- R10 and R11 are independently selected from the group consisting of:
- (1) hydrogen, (2) halogen, (3) C1-C6alkyl optionally substituted by hydroxy, (4) —COR wherein R is C1-C6alkyl optionally substituted by halogen, C1-C6alkoxy, or C3-C6cycloalkyl, (5) —CH2—COO—CH2CH3, —CH2—COOH, or —CH2—CH2—COOH, (6) S(O)2—C1-C6alkyl, (7) C3-C6cycloalkyl, (8) cyano, and (9) phenyl;
- or together R10 and R11 are C1-C6alkylene;
- A is CR17 or N, wherein R17 is hydrogen, halogen, C1-C6alkyl, C1-C6alkoxy or C2-C6alkenyl;
- B is CR18 or N, wherein R18 is hydrogen, halogen, C1-C6alkyl, C1-C6alkoxy or C2-C6alkenyl;
- D is CR19 or N, wherein R19 is hydrogen, halogen, C1-C6alkyl, C1-C6alkoxy, C2-C6alkenyl or phenyl;
- and
- E is CR20 or N, wherein R20 is hydrogen, halogen, C1-C6alkyl, C1-C6alkoxy or C2-C6alkenyl;
- or alternatively,
- E is CR20 and -A-B-D- is —N—O—, —NR21—N—, —S—N—, —S—CH— or —CH—S—, wherein R21 is hydrogen, halogen, C1-C6alkyl, C1-C6alkoxy or C2-C6alkenyl;
- or
- E is N and -A-B-D- is —N—O—, —S—N—, —S—CH—, —CH—CH— or —CH—S—;
- or
- E is S and -A-B-D- is —CH—CH—;
- and
- n is 1, 2 or 3.
38 more elements
A compound of selected from the group consisting of:
- N-(4-tert-Butyl-benzyl)-N-[2-(3,4-dichloro-phenyl)-ethyl]-2-((R)-2-hydroxymethyl-pyrrolidin-1-yl)-nicotinamide;
- N-(4-tert-Butyl-benzyl)-N-[2-(3,4-dichloro-phenyl)-ethyl]-2-pyrrolidin-1-yl-nicotinamide;
- 2-Azetidin-1-yl-N-(4-tert-butyl-benzyl)-N-[2-(3,4-dichloro-phenyl)-ethyl]-nicotinamide;
- 5-Chloro-2-methylamino-N-(4-methyl-benzyl)-N-[2-(3-trifluoromethyl-phenyl)-ethyl]-benzamide;
- 5-Chloro-N-(4-ethyl-benzyl)-2-methylamino-N-[2-(3-trifluoromethyl-phenyl)-ethyl]-benzamide;
- 5-Chloro-N-(4-ethyl-benzyl)-2-methylamino-N-[2-(3-trifluoromethyl-phenyl)-ethyl]-nicotinamide;
- N-(4-tert-Butyl-benzyl)-5-chloro-2-methylamino-N-(2-phenoxy-ethyl)-benzamide;
- 6-Chloro-3-methylamino-pyridine-2-carboxylic acid (4-tert-butyl-benzyl)-(2-phenoxy-ethyl)-amide;
- and
- a pharmaceutically acceptable salt thereof.
7 more elements
Dependencies are inferred from the claim text.