| US 7,579,352 B2 | ||
| Retinoic acid mimetic anilides | ||
| Dominique Mabire, La Saussaye (France); Christophe Denis Adelinet, Iville (France); Imré Christian Csoka, Louviers (France); and Marc Gaston Venet, Le Mesnil-Esnard (France) | ||
| Assigned to Janssen Pharmaceutica N.V., (Belgium) | ||
| Filed on Oct. 29, 2007, as Appl. No. 11/926,699. | ||
| Application 11/551045 is a division of application No. 11/081393, filed on Mar. 16, 2005, granted, now 7,179,825. | ||
| Application 11/081393 is a division of application No. 09/962551, filed on Sep. 25, 2001, granted, now 6,936,626. | ||
| Application 09/962551 is a division of application No. 09/555775, filed on Jun. 01, 2000, granted, now 6,319,939. | ||
| Application 11/926699 is a continuation of application No. 11/551045, filed on Oct. 19, 2006. | ||
| Claims priority of application No. 97203886 (EP), filed on Dec. 11, 1997. | ||
| Prior Publication US 2008/0058334 A1, Mar. 06, 2008 | ||
| Int. Cl. A61K 31/496 (2006.01); A61K 31/454 (2006.01); A61K 31/4439 (2006.01); A61K 31/4196 (2006.01); C07D 403/02 (2006.01); C07D 401/06 (2006.01); C07D 401/02 (2006.01); C07D 249/08 (2006.01) | ||
| U.S. Cl. 514—254.05 [514/326; 514/340; 514/383; 544/366; 546/210; 546/272.4; 548/262.2; 548/266.4; 548/267.2] | 11 Claims |
1. A compound having the formula
 X represents —O—, —S— or —NR3—;
R1 represents hydrogen, hydroxy, C1-6alkyl or aryl;
R2 represents hydrogen; C1-12alkyl; C3-7cycloalkyl; C2-8alkenyl; aryl; Het1; or C1-12alkyl substituted with one or two substituents selected from C3-7cycloalkyl, hydroxy, C1-4alkyloxy, cyano, amino, mono- and di(C1-4alkyl)amino, mono- or di(arylC1-4alkyl)amino, di(arylC1-4alkyl)aminocarbonyloxy, (C1-4alkyl) (arylC1-4alkyl)amino, mono- and di(aryl)amino, (C1-4alkyl)(di(C1-4alkyl)-aminoC1-4alkyl)amino, pyrrolidinyl, piperidinyl, piperazinyl optionally substituted with C1-4alkyl, morpholinyl, perhydro-azepinyl, carboxyl, C1-4alkyloxycarbonyl, aminocarbonyl, mono- and di(C1-4alkyl)aminocarbonyl, aryl, aryloxy or arylthio;
R3 represents hydrogen, C1-6alkyl, aryl, Het1 or C1-6alkyl substituted with aryl or Het1;
R4 represents hydrogen; hydroxy; mercapto; C1-6alkyloxy; C1-6alkylthio; aryloxy; arylthio; Het1-oxy; Het1-thio; C1-12alkyl; C1-12alkyl substituted with halo; C2-8alkenyl substituted with aryl; or —NR3R5 wherein R5 represents hydrogen, C1-6alkyl, aryl, Het1, (aryl or Het1)C1-6alkyl, (aryl or Het1)carbonyl or (aryl or Het1)C1-6alkyloxycarbonyl;
aryl represents indanyl, indenyl, naphtyl, 5,6,7,8-tetrahydro-2-naphtalenyl, phenyl; said indanyl, indenyl, naphtyl or phenyl
may be substituted with one, two, three, four or five substituents each independently selected from hydroxy, halo, nitro,
cyano, amino, azido, mono- or di(C1-6alkyl)amino, C1-6alkylcarbonylamino, C1-6alkyl, polyhaloC1-6alkyl, hydroxyC1-6alkyl, phenyl, phenyloxy, phenylC1-6alkyloxy, pyridinylC1-6alkyloxy, C1-6alkyloxy, formyl, carboxyl and C1-6alkylcarbonyl; or two adjacent carbon atoms on said phenyl may be substituted by a single bivalent radical having the formula
C1-12alkanediyl or polyhaloC1-12alkanediyl;
Het represents triazolyl which may optionally be substituted with amino, mercapto, C1-6alkyl, C1-6alkylthio or aryl; and
Het1 represents a monocyclic heterocycle selected from pyrrolidinyl, pyrrolyl, pyrazolyl, imidazolyl, 1,3,4-triazolyl, 1,2,4-triazolyl,
tetrahydrofuranyl, furanyl, thiolanyl, thienyl, dioxolanyl, isoxazolyl, oxazolyl, isothiazolyl, thiazolyl, isoxazolidinyl,
oxazolidinyl, isothiazolidinyl, thiazolidinyl, piperidinyl, pyridinyl, piperazinyl, pyridazinyl, pyrimidinyl, pyrazinyl, 1,2,3-triazinyl,
1,2,4-triazinyl, tetrahydropyranyl, pyranyl, morpholinyl and dioxanyl; each of said monocyclic heterocycles may be optionally
substituted with one or two substituents each independently selected from C1-4alkyl, hydroxy, amino, halo, aryl, arylcarbonyl or C1-4alkyloxycarbonyl; or a bicyclic heterocycle selected from indolinyl, indolyl, indazolyl, benzimidazolyl, benzotriazolyl, benzofuranyl,
benzothienyl, 2H-1-benzopyranyl, 3,4-dihydro-2H-1-benzopyranyl, benzthiazolyl, isoquinolinyl, quinolinyl, 3,4-dihydroquinolinyl,
cinnolinyl, quinazolinyl, quinoxalinyl, chromanyl, 1,4-benzodioxinyl, 1,4-benzoxathianyl, benzodioxanyl and benzodioxolanyl;
each of said bicyclic heterocycles may be substituted with one or two substituents each independently selected from C1-4alkyl, hydroxy, amino, halo, aryl, arylcarbonyl or C1-4alkyloxycarbonyl;
with the proviso the N-[4-(2-ethyl-1-[1,2,4]triazol-1-yl-butyl)-phenyl]-acetamide is not included.
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