(12) United States Patent (10) Patent No.: US 8,183,251 B2 Chapman Et Al

(12) United States Patent (10) Patent No.: US 8,183,251 B2 Chapman Et Al

USOO8183251B2 (12) United States Patent (10) Patent No.: US 8,183,251 B2 Chapman et al. (45) Date of Patent: May 22, 2012 (54) HYDANTOIN COMPOUNDS AND 7,132,434 B2 11/2006 Eriksson et al. PHARMACEUTICAL COMPOSITIONS 7,354,940 B2 4/2008 Henriksson et al. 7,368,465 B2 5/2008 Eriksson et al. THEREOF 7.427,631 B2 9, 2008 Eriksson et al. 7.625,934 B2 12/2009 Eriksson et al. (75) Inventors: David Chapman, Lund (SE); Balint 7,648,992 B2 1/2010 Gabos et al. 7,655,664 B2 2/2010 Gabos et al. Gabos, Lund (SE); Magnus Munck af 7,662,845 B2 2/2010 Henriksson et al. Rosenschöld, Lund (SE) 7,666,892 B2 * 2/2010 Eriksson et al. .............. 514/389 7,700,604 B2 4/2010 Gabos et al. (73) Assignee: AstraZeneca AB, Södertälje (SE) 7,754,750 B2 7/2010 Eriksson et al. 7,772.403 B2 8, 2010 Cornwall et al. (*) Notice: Subject to any disclaimer, the term of this 2002fOOO6920 A1 1/2002 Robinson et al. 2002fOO2.8835 A1 3/2002 Hu et al. patent is extended or adjusted under 35 2002fOO65219 A1 5, 2002 Naidu et al. U.S.C. 154(b) by 1046 days. 2002/009 1107 A1 7/2002 Madar et al. 2003/O130273 A1 7/2003 Sheppecket al. (21) Appl. No.: 11/946,517 2004/0044215 A1 3/2004 Alcade et al. 2004/0106659 A1 6/2004 AfRosenschold (22) Filed: Nov. 28, 2007 2004/O110809 A1 6/2004 Lepisto et al. 2004/O116486 A1 6/2004 Lepisto et al. (65) Prior Publication Data 2004/O127528 A1 7/2004 Eriksson et al. US 2008/0221 139 A1 Sep. 11, 2008 (Continued) FOREIGN PATENT DOCUMENTS Related U.S. Application Data EP O175312 3, 1986 (60) Provisional application No. 60/867,606, filed on Nov. (Continued) 29, 2006. (51) Int. Cl. OTHER PUBLICATIONS CO7D 403/2 (2006.01) Aharony et al. “Pharmacological Characterization of a New Class of CO7D 2.39/34 (2006.01) Nonpeptide Neurokinin A Antagonists that Demonstrate Species A6 IK3I/506 (2006.01) Selectivity.” J. Pharmacol. Exp. Ther. 274:3 (1995), pp. 1216-1221. (52) U.S. Cl. ........................................ 514/269; 544/298 Aigner et al., “Growth Plate Cartilage as Developmental Model in (58) Field of Classification Search .................. 544/298; Osteoarthritis Research-Potentials and Limitations”. Current Drug 51.4/269 Targets 8(2):377-385 (2007). See application file for complete search history. Aimoto et al. “Synthesis of Carriers of Differing Strokes Radius with Activated Acyl Groups for Use as Reagents in Labeling Membrane (56) References Cited Proteins.” Journal of Biological Chemistry, vol. 256(10), pp. 5134 5143, 1981. U.S. PATENT DOCUMENTS (Continued) 2,327,890 A 8, 1943 Henze 2,745,875 A 5, 1956 Ehrhart et al. 3,452,040 A 6/1969 Langis Primary Examiner — Deepak Rao 3,529,019 A 9, 1970 Suh et al. (74) Attorney, Agent, or Firm — Fish & Richardson P.C. 3,849,574 A 11/1974 Suh et al. 4,241,073. A 12, 1980 Jamieson et al. 4,315,031 A 2f1982 Vincent et al. (57) ABSTRACT 4,983,771 A 1/1991 Bryker et al. 5,068,187 A 11, 1991 Takeichi et al. The invention provides compounds of formula (I): 5,246,943 A 9/1993 Blankley et al. 5,308,853. A 5/1994 Hodges et al. 5,521,187 A 5/1996 Freyne et al. 5,804,593. A 9/1998 Warpehoski et al. 5,919,790 A 7, 1999 Allen et al. 5,955.435 A 9, 1999 Baxter et al. 6,046,214. A 4/2000 Kristiansen et al. 6,048,841 A 4/2000 Baxter et al. 6,114.361 A 9, 2000 Robinson et al. 6,159,995 A 12/2000 Thorwart et al. 6,166,041 A 12/2000 Cavalla et al. 6,218,418 B1 4/2001 Pevarello et al. 6,268.379 B1 7/2001 Xue et al. 6,277,987 B1 8/2001 Kukkola et al. wherein R' and Rare as defined in the specification; pro 6,291,685 B1 9/2001 Junghans et al. cesses for their preparation; pharmaceutical composi 6,329,418 B1 12/2001 Cheng et al. 6,339,101 B1 1/2002 Ross et al. tions containing them; a process for preparing the phar 6,340,691 B1 1/2002 Levin et al. maceutical compositions; and their use in therapy. The 6,429,213 B1 8, 2002 Xue et al. compounds are useful as MMP inhibitors. 6,890,915 B2 5/2005 Sheppecket al. 6,906,053 B2 6/2005 Sheppecket al. 7,078.424 B2 7/2006 Hamilton et al. 11 Claims, No Drawings US 8,183,251 B2 Page 2 U.S. PATENT DOCUMENTS WO WO 2004/020415 3, 2004 2004/O138276 A1 7/2004 Eriksson et al. W. W338; 3. 2004/O147573 A1 7/2004 Eriksson et al. WO WO 2004/O24715 3, 2004 2004/O152697 A1 8, 2004 Chan et al. WO WO 2004/O24718 3, 2004 2004/0209874 A1 10/2004 Sheppecket al. WO WO 2004/O24721 3, 2004 2004/0266832 A1 12/2004 Li et al. WO WO 2004/033632 4/2004 2005, OO19994 A1 1/2005 Chang WO WO 2004/108086 12, 2004 2005/0026990 A1 2/2005 Eriksson et al. WO WO 2006/004532 1, 2006 2005/0171096 A1 8/2005 Sheppecket al. WO WO 2006/004.533 1, 2006 2005/0245586 A1 11/2005 Henriksson et al. WO WO 2006/065215 6, 2006 2005/0256176 A1 11/2005 Burrows et al. WO WO 2006/065216 6, 2006 2006, OO19994 A1 1/2006 Burrows et al. WO WO 2006/077387 T 2006 2006, OO63818 A1 3, 2006 Burrows et al. WO WO 2007/106021 9, 2007 2006/0276524 A1 12/2006 Henriksson et al. WO WO 2007/106022 9, 2007 2008.00043.17 A1 1/2008 Gabos et al. 2008.OO32997 A1 2/2008 Gabos et al. OTHER PUBLICATIONS 2008, OO6471.0 A1 3/2008 Gabos et al. 2008.0171882 A1 7/2008 Eriksson et al. Avgeropoulos et al., “New Treatment Strategies for Malignant 2008/0221139 Al 9, 2008 Chapman et al. Gliomas'. The Oncologist 4:209-224 (1999). 2008/0262045 A1 10, 2008 Eriksson et al. Banfield et al., “Heterocyclic Derivatives of Guanidine. Part V. Reac 2008/0293743 A1 11/2008 Gabos et al. tion of Some Glycidic Esters with Guanidines”.. The Journal of the 2009.00546592008/0306.065 A1 12/20082/2009 CornwallEriksson etet al.al. Chemicalemical SociefSociety 51.2747-2756511:2747-2756 (1963).(1963 2009, 0221640 A1 9/2009 Briggner et al. Belvisi et al, The role ofmatrix metalloproteinases (MMPs) in the 2010, O144771 A1 6, 2010 Gabos et al. patho-physiology of chronic obstructive pulmonary disease (COPD): 2010/0256166 A1 10, 2010 Gabos et al. a therapeutic role for inhibitors of MMPs?”. Inflammation 2010/0273849 A1 10, 2010 Eriksson et al. Research 52:95-100 (2003). 2011/0003853 A1 1/2011 Eriksson et al. Borchers et al., “Acrolein-Induced MUC5ac Expression in Rat Air ways”. The American Physiological Society 274:L573-L581 (1998). FOREIGN PATENT DOCUMENTS Borkakoti, “Matrix metalloprotease inhibitors: design from struc EP O2126.17 3, 1987 ture'. Biochemical Society Transactions 32:17-20 (2004). EP O255390 2, 1988 Bright etal. "Monoclonal Antibodies as Surrogate Receptors in High EP O442584 8, 1991 Throughput Screen for Compounds that Enhance Insulin Sensitiv EP O5802100486,280 5,1, 19941992 ity”itv. Life Sciences.Sci 61:23 (1997),(1997 pp. 2305-23152305-2315. EP O640594 3, 1995 Bruce et al., “The effect of marimastat, a metalloprotease inhibitor, EP O7.09375 5, 1996 on allergen-induced asthmatic hyper-activity. Toxicol. & Appl. EP 1397137 11, 1996 Pharmacol. 205:126-132 (2005). EP O909754 4f1999 Carmeliet, “Proteinases in Cardiovascular Aneurysms and Rupture: EP 1117616 T 2001 Targets for Therapy?', The Journal of Clinical Investigation EP 1149843 10, 2001 EP 1191024 3, 2002 105(11): 1519-1520 (2000). EP 1550725 7/2005 Catterall et al., “Drugs in development: bisphosphonates and metal WO WO92/01062 1, 1992 loproteinase inhibitors'. Arthritis Res Ther 5:12-24 (2003). WO WO95/14025 5, 1995 Chambers et al., “Changing Views of the Role of Matrix Metal WO WO96/21640 T 1996 loproteinases in Metastasis', J Natl Cancer Inst 89:1260-1270 WO WO96,27583 9, 1996 (1997). WO WO 98.50359 11, 1998 Chemical Abstracts, vol. 65, 1966, ABSTRACT No. 13684 h., M. WO WO99.24399WO99,06361 2,5, 1999 Lora-Tora-1amayo etit al.:al. "PotentialPotenual anticanceranti agents.ts. 1.I. GlutamiGlutamine WO WO99,42443 8, 1999 Sulfonate analogs'. & Anales Real Soc. Espan. Fis. Quim (Madrid), WO WO99.62880 12/1999 Ser. B. 62(2), 173-86. WO WOOOO9103 2, 2000 Chodosh et al., “Comparative trials of doxycycline versus amoxicil WO WOOOf 12477 3, 2000 lin, cephalexin and enoxacin in bacterial infections in chronic bron WO WOOOf 12478 3, 2000 chitis and asthma'. Scand. J. Infect. Dis. Suppl.53:22-8 (1988). WO WOOO,35886 6, 2000 Comber et al., “5.5-Disubstituted Hydantoins: Syntheses and Anti W W 8:37. 3. HIV Activity”, J Med. Chem. 35:3567-3572 (1992). WO WOOOf 75106 12/2000 9ptp:/www.lungsonline.com cop html downloaded Aug. WO WOO1 (05756 1, 2001 & 8 WO WOO1? 12189 2, 2001 Croce, P. et al. “Stereoselective aldol additions of a chirai glycine WO WOO1,223.63 3, 2001 enloate synthon to heteroaromatic aldehydes.” Heterocycles, 52:3 WO WOO1/34573 5, 2001 (2000) pp. 1337-1344. WO WOO2,06232 1, 2002 Dahan et al., “Expression of Matrix Metalloproteinases in Healthy WO WO O2, 14262 2, 2002 and Diseased Human Gingiva'.

View Full Text

Details

  • File Type
    pdf
  • Upload Time
    -
  • Content Languages
    English
  • Upload User
    Anonymous/Not logged-in
  • File Pages
    19 Page
  • File Size
    -

Download

Channel Download Status
Express Download Enable

Copyright

We respect the copyrights and intellectual property rights of all users. All uploaded documents are either original works of the uploader or authorized works of the rightful owners.

  • Not to be reproduced or distributed without explicit permission.
  • Not used for commercial purposes outside of approved use cases.
  • Not used to infringe on the rights of the original creators.
  • If you believe any content infringes your copyright, please contact us immediately.

Support

For help with questions, suggestions, or problems, please contact us