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(12) United States Patent (10) Patent No.: US 8,877,934 B2 Berger Et Al

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(12) United States Patent (10) Patent No.: US 8,877,934 B2 Berger Et Al US008877934B2 (12) United States Patent (10) Patent No.: US 8,877,934 B2 Berger et al. (45) Date of Patent: Nov. 4, 2014 (54) N-HETEROARYL COMPOUNDS (52) U.S. Cl. CPC ............ C07D 213/89 (2013.01); C07D401/04 (75) Inventors: Michael Berger, Schwabenheim (DE); (2013.01); C07D 213/74 (2013.01); C07D Christopher Kern, Schwabenheim 239/47 (2013.01); C07D 239/42 (2013.01); (DE); Marko Eck, Schwabenheim (DE): C07D 413/04 (2013.01); C07D491/048 Jörg Schröder, Schwabenheim (DE) (2013.01); C07D 471/04 (2013.01); C07D 215/46 (2013.01) (73) Assignee: Intervet Inc., Summit, NJ (US) USPC ........................................ 546/309; 514/235.8 (58) Field of Classification Search (*) Notice: Subject to any disclaimer, the term of this None patent is extended or adjusted under 35 See application file for complete search history. U.S.C. 154(b) by 0 days. (56) References Cited (21) Appl. No.: 13/876,724 FOREIGN PATENT DOCUMENTS (22) PCT Filed: Sep. 28, 2011 CN 1.01284.812 A 10, 2008 EP 1900 772 A2 3, 2008 (86). PCT No.: WO 2004/03.5591 A1 4/2004 WO 2008/028689 A1 3, 2008 S371 (c)(1), WO 2008/028691 A1 3, 2008 (2), (4) Date: Mar. 28, 2013 OTHER PUBLICATIONS (87) PCT Pub. No.: WO2012/041873 Silva, A., Mini-Reviews in Medicinal Chemistry, 2005, vol. 5, pp. 893-1014.* PCT Pub. Date: Apr. 5, 2012 Jabbar et al., “Anthelmintic resistance: the sate of play revisited'. Life Sciences, 2006, pp. 2413-2431, vol. 79. (65) Prior Publication Data McKellar et al., “Veterinary anthelmintics: old and new”, Trends in US 2013/O196993 A1 Aug. 1, 2013 Parasitology, 2004, pp. 456-461, vol. 20010). International Search Report for corresponding PCT/EP2011/066806, mailed Dec. 14, 2011. Golisade, et al., “Anti-Malarial Activity of N6- Substituted Related U.S. Application Data Adenosine Derivates. Part I, Bioorganic & Medical Chemistry, (60) Provisional application No. 61/388,466, filed on Sep. 2002, pp. 769-777, vol. 10. 30, 2010. * cited by examiner (30) Foreign Application Priority Data Primary Examiner — Heidi Reese (57) ABSTRACT Sep. 29, 2010 (EP) ..................................... 10181553 This invention relates to certain N-heteroaryl compounds that (51) Int. Cl. are generally useful as medicaments, more specifically as A 6LX3/535 (2006.01) medicaments for animals. The medicament can preferably be CO7D 23/00 (2006.01) used for the treatment of helminth infections and the treat CO7D40 L/04 (2006.01) ment of parasitosis, such as caused by helminth infections. C07D 213/89 (2006.01) This invention also relates to uses of the compounds to make C07D 213/74 (2006.01) medicaments and treatments comprising the administration C07D 239/47 (2006.01) of the compounds to animals in need of the treatments. This CO7D 239/42 (2006.01) invention also relates to novel N-heteroaryl compounds and CO7D 413/04 (2006.01) the preparation of said compounds. Moreover this invention CO7D 49/048 (2006.01) relates to pharmaceutical compositions and kits comprising CO7D 47L/04 (2006.01) the compounds. CO7D 215/46 (2006.01) 21 Claims, No Drawings US 8,877,934 B2 1. 2 N-HETEROARYL COMPOUNDS SUMMARY OF THE INVENTION CROSS-REFERENCE TO RELATED Briefly, this invention relates to compounds that can gen APPLICATIONS erally be used as a medicament for animals. The compounds 5 correspond in structure to formula (I) or its pharmaceutically This application is a national stage entry under 35 U.S.C. acceptable salts, Solvates, N-oxides or prodrugs S371 of PCT/EP2011/066806, filed on Sep. 28, 2011, which claims priority to U.S. Provisional Application No. 61/388, 466, filed on Sep. 30, 2010, and EP Application No. Formula (I) 10181553.8, filed on Sep. 29, 2010. The content of PCT/ 10 EP2011/066806 is hereby incorporated by reference in its entirety. FIELD OF THE INVENTION 15 This invention relates to novel N-heteroaryl compounds that are useful as medicaments, the preparation of Such com pounds and the use of Such compounds. The medicament can preferably be used for the treatment of parasitic infections o such as helminth infections and especially for the treatment of parasitoses, such as caused by helminth infections. This invention also relates to uses of the compounds to make medicaments and treatments comprising the administration of the compounds to animals in need of the treatments. More- 25 over this invention relates to pharmaceutical compositions and kits comprising the compounds. wherein R" is halogen, C-C-alkyl, C-C-alkyloxy, C-C-alky BACKGROUND OF THE INVENTION lthio, C-C-alkenyl, C-C-alkynyl, C-C-alkyloxy C-C- 30 alkyl, C-C-alkylthio C-C-alkyl, C-C-alkyl carbonyl, Parasitic diseases in animals cause Substantial Suffering C-C-alkenyl carbonyl, SFs, C-C-alkyl sulfonyl, wherein and economic losses throughout the world. Thus, treatment of each of the carbon-containing radicals optionally is substi parasitic infections remains an important global endeavor. tuted by one or more halogen atoms, preferably fluorine The causative organisms include helminths, such as nema atoms, todes, cestodes, and trematodes. These organisms can infect, 35 R is hydrogen, halogen, C1-Co-alkyl, C1-Co-alkyloxy, for example, the stomach, intestinal tract, lymphatic system, C-C-alkylthio. C-C-alkenyl, C-C-alkynyl, C-C-alky muscle tissues, kidney, liver, lungs, heart, and brain of ani loxy C-C-alkyl, C-C-alkylthio C-C-alkyl, C-C-alkyl mals. There are many known drugs (or “anthelmintic agents”) carbonyl, C-C-alkenyl carbonyl, wherein each of the car available to treat various helminith parasite infections, see, 40 bon-containing radicals optionally is Substituted by one or e.g., McKellar, Q. A., et al., “Veterinary anthelmintics: old more halogen atoms, preferably fluorine atoms, and new. Review: Trends in Parasitology, 20010), 456-61 R is hydrogen, C-C-alkyl or cycloalkyl, preferably (October 2004). These anthelmintic agents treat specifically hydrogen, either nematode, cestode or trematode infections or have a R" is hydrogen, C-C-alkyl or cycloalkyl preferably broader anthelmintic spectrum. An example of an anthelm- 45 hydrogen, intic agent with sole effect on cestodes (tapeworms) is prazi R is hydrogen, C-C-alkyl, cycloalkyl, acyl or C-C- quantel. Some primary nematicidal compounds like fen alkyloxycarbonyl, bendazole, mebendazole, oxfendazole, albendazole have a R is hydrogen, C1-Co-alkyl, cycloalkyl, hydroxy, C, -Co broader spectrum than nematodes and treat cestode infections alkyloxy, phenyl C-C-alkyloxy, hydroxy C-C-alkyl, as well. Closantel, rafoxanide and triclabendazole are 50 C-C-alkyloxy C-C-alkyl, phenyl C-C-alkyloxy C-C- examples of specific compounds for the treatment of trema alkyl, thiol C-C-alkyl, C-C-alkylthio C-C-alkyl, phenyl tode infections (flukes). C-C-alkylthio C-C-alkyl, hydroxycarbonyl, hydroxycar While many parasitic infections can be treated with known bonyl C-C-alkyl, C-C-alkyloxycarbonyl, C-C-alky drugs, evolutionary development of resistance by the para loxycarbonyl C-C-alkyl, aminocarbonyl, aminocarbonyl sites can render Such drugs obsolete over time, see, e.g., 55 C-C-alkyl, C-C-alkylaminocarbonyl, C-C-alkylami Jabbar, A., et al., “Anthelmintic resistance: the state of play nocarbonyl (C-C-alkyl), di(C-C-alkyl)aminocarbonyl, revisited.” Life Sciences, 79, 2413-31 (2006). In addition, di (C-C-alkyl)aminocarbonyl (C-C-alkyl), C-C-alky known drugs may have other deficiencies, such as limited lamino C-C-alkyl, di(C-C-alkyl)amino C-C-alkyl, phe spectrum of activity and the need for repeated treatments. nyl, phenyl C-C-alkyl, wherein each phenyl group is In WO 2008/028689 A1 certain N-(1-phtalazin-1-ylpiperi- 60 optionally Substituted by hydroxy, C-C-alkyloxy or din-4-yl)-amides are described as EP2 receptor modulators. cycloalkyloxy WO 2008/028691 A1 discloses as EP2 receptors certain R’ is hydrogen, C-C-alkyl or cycloalkyl or R is joined N-(1-hetaryl-piperidin-4-yl)(het)arylamides. together with R to form a C-C-alkylene group and R7 is There still exists a need for new medicaments, such as joined together with R to form a C-C-alkylene group, antiparasitic agents to ensure safe, effective, and convenient 65 wherein one or both of said C-C-alkylene groups are treatment of a wide range of parasitic helminth infections optionally Substituted by one or more C-C-alkyl or over a long period of time. cycloalkyl radicals, US 8,877,934 B2 3 4 n is an integer from 1 to 3. This invention also relates to compounds according to for X is a carbonyl, thiocarbonyl or Sulfonyl group, preferably mula (Ia) or its pharmaceutically acceptable salts, Solvates or a carbonyl group, N-oxides A is a bond or NR, wherein R is hydrogen or C-C-alkyl, preferably hydrogen, E is a bond or NR, wherein R is hydrogen or C-C-alkyl, preferably hydrogen, Formula (Ia) B is N or CR', wherein R' is hydrogen or C-C-alkyl, preferably hydrogen, D is N or CR'', wherein R'' is hydrogen or C-C-alkyl, preferably hydrogen, 10 Y' is C or N, wherein C is substituted by R' which is hydrogen, halogen, C-C-alkyl, C-C-alkenyl, Cycloalkyl, Cycloalkyloxy, C-C-haloalkyl, C-C-alkoxy, C-C-ha loalkoxy, nitrilo, nitro, amino, C-C-alkylamino, Cycloalky lamino, di(C-C-alkyl)amino, (C-C-alkyl)-(Cycloalkyl) 15 amino, N-pyrrolidinyl, N-piperidinyl, N-morpholinyl, C-C-alkylthio, Cycloalkylthio, C-C-haloalkylthio. C-C-alkyl carbonyl, C-C-haloalkyl carbonyl, C-C- alkylcarbonylamino, aminocarbonyl, C-C-alkylaminocar bonyl, di(C-C-alkyl)aminocarbonyl, C-C-alkoxycarbo nyl, phenyl, dioxolane Such as 1,3-dioxolane, dioxane Such as 1,3-dioxane, or dioxepane Such as 1,3-dioxepane, each said ring being unsubstituted or substituted by C-C-alkyl, Y’ is C or N, wherein C is substituted by R' which is wherein hydrogen, halogen, C-C-alkyl, C-C-alkenyl, Cycloalkyl, 25 R" is hydrogen, halogen, C-C-alkyl, cycloalkyl, C-C- Cycloalkyloxy, C-C-haloalkyl, C-C-alkoxy, C-C-ha alkyloxy, cycloalkyloxy, C-C-alkylthio, cycloalkylthio.
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