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Is-N-C-O--N 71 (58) Field of Classification Search US008158657B2 (12) United States Patent (10) Patent No.: US 8,158,657 B2 Tanaka et al. (45) Date of Patent: Apr. 17, 2012 (54) HETEROCYCLES SUBSTITUTED PYRIDINE 6,080,767 A 6/2000 Klein et al. DERVATIVES AND ANTIFUNGALAGENT 6,140,131 A 10/2000 Sunakawa et al. 6,174.905 B1 1/2001 Suzuki et al. CONTAINING THEREOF 6,200,975 B1 3/2001 Carling et al. 6,235,728 B1 5, 2001 Golik et al. (75) Inventors: Keigo Tanaka, Tsukuba (JP); Satoshi 6.255,318 B1 7/2001 Bedard et al. 6,310,203 B1 10/2001 Carling et al. Inoue, Tsukuba (JP); Norio Murai, 6,313,127 B1 1 1/2001 Waterson et al. Tsukuba (JP); Masayuki Matsukura, 6,319,944 B1 1 1/2001 Claiborne et al. Tsukuba (JP); Kazutaka Nakamoto, 6,340,690 B1 1/2002 Bachand et al. Tsukuba (JP); Shuji Shirotori, Tsukuba 6,380,218 B1 4/2002 Marfat et al. (JP); Shinya Abe, Tsukuba (JP) 6,407,116 B1 6/2002 Kajino et al. (Continued) (73) Assignee: Eisai R&D Management Co., Ltd., Tokyo (JP) FOREIGN PATENT DOCUMENTS DE 1972.71 17 A1 1, 1999 (*) Notice: Subject to any disclaimer, the term of this (Continued) patent is extended or adjusted under 35 U.S.C. 154(b) by 0 days. OTHER PUBLICATIONS Okawa et al., Synthesis, No. 10. pp. 1467-1475 (1998). (21) Appl. No.: 12/704,637 AKos Screening Library, Feb. 7, 2006. CAS Registry No. 434304 24-2. (22) Filed: Feb. 12, 2010 Aurora Screening Library, Jan. 1, 2007, CAS Registry No. (RN): 431922-54-2. (65) Prior Publication Data US 2010/O168173 A1 Jul. 1, 2010 (Continued) Primary Examiner — Patricia Morris Related U.S. Application Data (74) Attorney, Agent, or Firm — Birch, Stewart, Kolasch & (62) Division of application No. 1 1/589,128, filed on Oct. Birch, LLP 30, 2006, now Pat. No. 7,691,882. (57) ABSTRACT (60) Provisional application No. 60/731,267, filed on Oct. 31, 2005, provisional application No. 60/753,391, An object of the present invention is to provide an antifungal filed on Dec. 27, 2005. agent which has excellent antifungal effects and is Superior in terms of its physical properties, safety and metabolic stability. (30) Foreign Application Priority Data According to the present invention, there is disclosed a com pound represented by the following formula (I), or a salt Oct. 31, 2005 (JP) ................................. 2005-31768O thereof: Dec. 27, 2005 (JP) ................................. 2005-374.395 (51) Int. Cl. (I) A6 IK3I/443 (2006.01) N CO7D 413/04 (2006.01) (52) U.S. Cl. ..................................... 514/340; 546/272.1 is-N-C-O--N 71 (58) Field of Classification Search ............... 546/272.1; 2 514/340 RI N R2 See application file for complete search history. wherein R' represents a hydrogen atom, a halogen atom, an (56) References Cited amino group, a C- alkyl group, a Coalkoxy group or a C alkoxy C, alkyl group; R represents a hydrogen atom, a U.S. PATENT DOCUMENTS C- alkyl group, an amino group or a di C-alkylamino 4,576.956 A 3, 1986 Makisumi et al. 4,720.493 A 1, 1988 Kawakita et al. group; one of X and Y is a nitrogen atom while the other is a 4,785,010 A 11, 1988 Zoller et al. nitrogen atom or an oxygen atom; ring A represents a 5- or 5,034,393 A 7, 1991 Hackler et al. 6-member heteroaryl ring or a benzene ring which may have 5,070,082 A 12/1991 Murdocket al. a halogen atom, or 1 or 2 C- alkyl groups; Z represents a 5,208,247 A 5, 1993 Trova et al. single bond, a methylene group, an ethylene group, an oxygen 5,296.484 A 3/1994 Coghlan et al. 5,328,921 A 7, 1994 Trova et al. atom, a sulfur atom, —CH2O— —OCH , —NH-. 5,350,749 A 9, 1994 Hackler et al. CH-NH , -NHCH , —CHS , or -SCH. : R 5,371,086 A 12/1994 Takemoto et al. represents a hydrogen atom, a halogen atom, a C- alkyl 5,691,136 A 1 1/1997 Lupski et al. group, a C-8 cycloalkyl group, a Co-o aryl group, a 5- or 5,691,336 A 11/1997 Dornet al. 5,710, 171 A 1/1998 Dinsmore et al. 6-member heteroaryl group, or 5- or 6-member non-aromatic 5,747,518 A 5, 1998 Yoshikawa et al. heterocyclic group which may have 1 or 2 substituents; and 5,852,042 A 12/1998 Jakobi et al. R" represents a hydrogen atom or a halogen atom. 5,945,431 A 8, 1999 Jin et al. 6,022,884 A 2/2000 Mantlo et al. 14 Claims, No Drawings US 8,158,657 B2 Page 2 U.S. PATENT DOCUMENTS JP 2001-5258O2 A 12/2001 6,414,013 B1 7/2002 Fancelli et al. E 39939, 338. 6,596,718 B1 7/2003 Flohr et al. JP 2002-284766. A 10, 2002 6,630,495 B1 10/2003 Cooke et al. JP 2002-537396 A 1 1/2002 7,179,804 B2 2/2007 Amegadzie et al. JP 2002-544162 A 12/2002 7,179,822 B2 2/2007 Bunker et al. 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