| US 7,601,751 B2 | ||
| Indole acetic acid acyl guanidines as β-secretase inhibitors | ||
| Lorin A. Thompson, III, Higganum, Conn. (US); Jianliang Shi, Hamden, Conn. (US); F. Christopher Zusi, Hamden, Conn. (US); Michael F. Dee, Madison, Conn. (US); and John E. Macor, Guilford, Conn. (US) | ||
| Assigned to Bristol-Myers Squibb Company, Princeton, N.J. (US) | ||
| Filed on Aug. 23, 2006, as Appl. No. 11/508,481. | ||
| Claims priority of provisional application 60/713316, filed on Sep. 01, 2005. | ||
| Prior Publication US 2007/0049589 A1, Mar. 01, 2007 | ||
| Int. Cl. A61K 31/404 (2006.01); A61K 31/5377 (2006.01); C07D 209/04 (2006.01); C07D 413/12 (2006.01); C07D 241/04 (2006.01) | ||
| U.S. Cl. 514—419 [548/469; 548/494; 548/495; 544/111; 544/143; 544/358; 514/415; 514/235.2; 514/252.13] | 6 Claims |
1. A compound of Formula (I); or a stereoisomer thereof
 R1 is phenyl optionally substituted with one or more groups selected from halogen, CN, CF3, OH, —NH2, —CH═CH-phenyl, pyridyl, thienyl, C3-6cycloalkyl, C1-6alkoxy, C2-6alkenyl, OR21, C1-6alkyl optionally substituted with OH or —NH2, —CH═CH—C1-4alkyl optionally substituted with C1-4alkoxy or OH, phenyl optionally substituted with halogen, —(CH2)m—NHC(═O)OC1-6 alkyl optionally substituted with R17, —(CH2)m—NHC(═O)Ophenyl optionally substituted with halogen, —(CH2)m—NHC(═O)R18, —NH(C═O)R19, —CH2NH(SO2)R20, —CH2morpholino and 4-methylpiperazinyl;
R2 and R3 are each independently hydrogen, methyl or hydroxymethyl;
m is 0 or 1;
R4 and R5 are each independently hydrogen or methyl;
R6 is hydrogen, C1-6alkyl, C1-6alkyl NHC(═O) or CN;
R7 is hydrogen, C1-6 alkyl, or phenylmethyl in which said phenyl is optionally substituted with one or more groups selected from halogen, CN, CF3, and OCH3;
R8 is hydrogen, halogen, C1-6alkyl, C1-4alkoxy, CN, OH, NH2, benzyloxy or CF3;
R17 is C1-4alkoxy, halogen, C2-3alkynyl, 4-nitrophenyl, benzyloxy or benzothiophene 1,1-dioxide;
R18 is C1-6alkyl or C3-6cycloalkyl in which each are optionally substituted with a group selected from halogen, CN, CF3, —N(CH3)2, C1-4alkoxy, C3-6cycloalkyl, morpholino, thienyl, imidazolyl, pyridyl, azepinyl, benzothienyl, benzofuranyl, phenyl and methoxyphenyl;
R19 is C1-6alkyl, C1-4alkoxy, C3-6cycloalkyl optionally substituted with —N(CH3)2 or methylthio, phenyl, pyridyl optionally substituted with one or two halogen and C1-4alkyl, benzothienyl, 1-methyl-2-pyrrolyl or furanyl;
R20 is C1-6alkyl, 1,2-dimethyl-1H-imidazolyl, thienyl or phenyl in which said phenyl is optionally substituted with a group selected
from acetyl, C1-4alkoxy, benzyloxy, halogen, NH(C═O)CH3 and nitro; and
R21 is C1-6alkyl optionally substituted with a group selected from C1-4alkoxy, halogen, phenyl, furanyl and methylamino;
or a nontoxic pharmaceutically acceptable salt thereof.
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