Tachykinin neurokinin 3 receptor antagonists: A patent review (2005 2010)

Expert Opinion on Therapeutic Patents

Volumn 21, Issue 5, 2011, Pages 637-655

  Malherbe, Pari ^a   Ballard, Theresa M ^a   Ratni, Hassen ^a  

^a F HOFFMANN LA ROCHE LTD   (Switzerland)

Author keywords

NK3 receptor; NKB; osanetant; psychosis; reproduction; schizophrenia; tachykinin; talnetant; testosterone

Indexed keywords

AZD 2624; GONADORELIN AGONIST; GSK 1144814; GSK 172981; GSK 256471; IMIDAZOLE DERIVATIVE; NEUROKININ 1 RECEPTOR; NEUROKININ 1 RECEPTOR ANTAGONIST; NEUROKININ 2 RECEPTOR; NEUROKININ 2 RECEPTOR ANTAGONIST; NEUROKININ 3 RECEPTOR; NEUROKININ 3 RECEPTOR ANTAGONIST; NEUROKININ B; OSANETANT; PLACEBO; PYRAZOLE DERIVATIVE; QUINOLINE DERIVATIVE; SCH 206272; SEX HORMONE; TALNETANT; UNCLASSIFIED DRUG;

ADVANCED CANCER; AMINO ACID SEQUENCE; BREAST CANCER; DOSE RESPONSE; DRUG EFFECT; DRUG EFFICACY; DRUG INDUSTRY; DRUG SAFETY; DRUG STRUCTURE; HUMAN; NONHUMAN; PHASE 1 CLINICAL TRIAL (TOPIC); PHASE 2 CLINICAL TRIAL (TOPIC); PROSTATE CANCER; REPRODUCTION; REVIEW; SCHIZOPHRENIA; SIGNAL TRANSDUCTION;

AMINO ACID SEQUENCE; ANIMALS; CLINICAL TRIALS AS TOPIC; HUMANS; LUTEINIZING HORMONE; MOLECULAR SEQUENCE DATA; NEOPLASMS, HORMONE-DEPENDENT; PATENTS AS TOPIC; RECEPTORS, NEUROKININ-3; REPRODUCTION; SCHIZOPHRENIA; TESTOSTERONE;

EID: 79955094637     PISSN: 13543776     EISSN: None     Source Type: Journal    
DOI: 10.1517/13543776.2011.568482     Document Type: Review

References (116)

1. Alexander SP, Mathie A, Peters JA. Guide to Receptors and Channels (GRAC), 3rd edition. Br J Pharmacol 2008;153:S1-209
2. Almeida TA, Rojo J, Nieto PM, et al. Tachykinins and tachykinin receptors: structure and activity relationships. Curr Med Chem 2004;21:2045-81 (Pubitemid 38967729)
3. Beaujouan JC, Torrens Y, Saffroy M, et al. A 25 year adventure in the field of tachykinins. Peptides 2004;25:339-57 (Pubitemid 38591548)
4. Severini C, Improta G, Falconieri-Erspamer G, et al. The tachykinin peptide family. Pharmacol Rev 2002;54:285-322 (Pubitemid 34575718)
5. Sarau HM, Griswold DE, Potts W, et al. Nonpeptide tachykinin receptor antagonists: I. Pharmacological and pharmacokinetic characterization of SB 223412, a novel, potent and selective neurokinin-3 receptor antagonist. J Pharmacol Exp Ther 1997;281:1303-11 (Pubitemid 27258390)
6. Emonds-Alt X, Bichon D, Ducoux JP, et al. SR 142801, the first potent non-peptide antagonist of the tachykinin NK3 receptor. Life Sci 1995;56:PL27-32 (Pubitemid 24372617)
7. Nguyen-Le XK, Nguyen QT, Gobeil F, et al. Pharmacological characterization of SR 142801: a new non-peptide antagonist of the neurokinin NK-3 receptor. Pharmacology 1996;52:283-91 (Pubitemid 26164706)
8. Giardina GA, Raveglia LF, Grugni M, et al. Discovery of a novel class of selective non-peptide antagonists for the human neurokinin-3 receptor. 2. Identification of (S)-N-(1-phenylpropyl)- 3-hydroxy-2-phenylquinoline-4- carboxamide (SB 223412).J Med Chem 1999;42:1053-65 (Pubitemid 29153434)
9. Langlois X, Wintmolders C, te Riele P, et al. Detailed distribution of neurokinin 3 receptors in the rat, guinea pig and gerbil brain: a comparative autoradiographic study. Neuropharmacology 2001;40:242-53
10. Shughrue PJ, Lane MV, Merchenthaler I. In situ hybridization analysis of the distribution of neurokinin-3 mRNA in the rat central nervous system. J Comp Neurol 1996;372:395-414 (Pubitemid 26277010)
11. Stoessl AJ. Localization of striatal and nigral tachykinin receptors in the rat. Brain Res 1994;646:13-18 (Pubitemid 24140148)
12. Nagano M, Saitow F, Haneda E. Distribution and pharmacological characterization of primate NK-1 and NK-3 tachykinin receptors in the central nervous system of the rhesus monkey. Br J Pharmacol 2006;147:316-23 (Pubitemid 43214689)
13. Chung FZ, Wu LH, Tian Y, et al. Two classes of structurally different antagonists display similar species preference for the human tachykinin neurokinin3 receptor. Mol Pharmacol 1995;48:711-16
14. Leffler A, Ahlstedt I, Engberg S, et al. Characterization of species-related differences in the pharmacology of tachykinin NK receptors 1, 2 and 3. Biochem Pharmacol 2009;77:1522-30
15. Meltzer H, Prus A. NK3 receptor antagonists for the treatment of schizophrenia. Drug Discov Today Ther Strat 2006;3:555-60 (Pubitemid 46076182)
16. Spooren W, Riemer C, Meltzer H. Opinion: NK3 receptor antagonists: the next generation of antipsychotics? Nat Rev Drug Discov 2005;4:967-75
17. Harrison PJ. The neuropathology of schizophrenia. A critical review of the data and their interpretation. Brain 1999;122:593-624
18. Marco N, Thirion A, Mons G, et al. Activation of dopaminergic and cholinergic neurotransmission by tachykinin NK3 receptor stimulation: an in vivo microdialysis approach in guinea pig. Neuropeptides 1998;32:481-8 (Pubitemid 28509015)
19. Dawson LA, Cato KJ, Scott C, et al. In vitro and in vivo characterization of the non-peptide NK3 receptor antagonist SB-223412 (talnetant): potential therapeutic utility in the treatment of schizophrenia. Neuropsychopharmacology 2008;33:1642-52 (Pubitemid 351684711)
20. Nordquist RE, Delenclos M, Ballard TM, et al. Cognitive performance in neurokinin 3 receptor knockout mice. Psychopharmacology (Berl) 2008;198:211-20
21. Evangelista S. Talnetant GlaxoSmithKline. Curr Opin Investig Drugs 2005;6:717-21 (Pubitemid 40904043)
22. Meltzer HY, Arvanitis L, Bauer D, et al. Placebo-controlled evaluation of four novel compounds for the treatment of schizophrenia and schizoaffective disorder. Am J Psychiatry 2004;161:975-84 (Pubitemid 38735983)
23. Liem-Moolenaar M, Gray FA, de Visser SJ, et al. Psychomotor and cognitive effects of a single oral dose of talnetant (SB223412) in healthy volunteers compared with placebo or haloperidol. J Psychopharmacol 2010;24:73-82
24. Dawson LA, Smith PW. Therapeutic utility of NK3 receptor antagonists for the treatment of schizophrenia. Curr Pharm Des 2010;16:344-57
25. Simonsen KB, Juhl K, Steiniger-Brach B, et al. Novel NK(3) receptor antagonists for the treatment of schizophrenia and other CNS indications. Curr Opin Drug Discov Devel 2010;13:379-88
26. Attwood TK. A compendium of specific motifs for diagnosing GPCR subtypes. Trends Pharmacol Sci 2001;22:162-5 (Pubitemid 32244299)
27. Nygaard R, Frimurer TM, Holst B, et al. Ligand binding and micro-switches in 7TM receptor structures. Trends Pharmacol Sci 2009;30:249-59
28. Palczewski K, Kumasaka T, Hori T, et al. Crystal structure of rhodopsin: a G protein-coupled receptor. Science 2000;289:739-45 (Pubitemid 30650186)
29. Malherbe P, Bissantz C, Marcuz A, et al. Me-talnetant and osanetant interact within overlapping but not identical binding pockets in the human tachykinin neurokinin 3 receptor transmembrane domains. Mol Pharmacol 2008;73:1736-50 (Pubitemid 351724361)
30. Malherbe P, Kratzeisen C, Marcuz A, et al. Identification of a critical residue in the transmembrane domain 2 of tachykinin neurokinin 3 receptoraffecting the dissociation kinetics and antagonism mode of osanetant (SR 142801) and piperidine-based structures. J Med Chem 2009;52:7103-12
31. Astrazeneca AB. Preparation of morpholinylazetidines as neurokinin receptor antagonists for treating gastrointestinal disorders. US270399; 2007
32. Astrazeneca AB. Preparation of azetidine derivatives as neurokinin receptor antagonists for treatment of gastrointestinal diseases. WO137790; 2006
33. Astrazeneca AB. Preparation of azetidine derivatives as neurokinin receptor antagonists for treatment of gastrointestinal diseases. WO137791; 2006
34. Astrazeneca AB. Preparation of azetidinyl compounds as neurokinin antagonists for treating gastrointestinal disorder. WO136325; 2007
35. Astrazeneca AB. Preparation of azetidinyl compounds as neurokinin antagonists for treating gastrointestinal disorder. US270400; 2007
36. Astrazeneca AB. Azetidine compounds as neurokinin receptor antagonists, their preparation, pharmaceutical compositions, and use in therapy. WO037743; 2007
37. Astrazeneca AB. Preparation of azetidinylpiperidine compounds as neurokinin antagonists for treating gastrointestinal disorders. WO136324; 2007
38. Astrazeneca AB. Preparation of azetidinepiperazine derivatives as neurokinin receptor antagonists for treatment of gastrointestinal disorders. WO076042; 2008
39. Astrazeneca AB. Preparation of cyanophenylethyl quinolinecarboxamides as neurokinin-3 (NK-3) receptor ligands. WO035157; 2007
40. Astrazeneca AB. Amide substituted quinolines, processes for preparing them, pharmaceutical compositions containing them, and their use as modulators of neurokinin-3 (NK-3) receptors. WO086799; 2007
41. Astrazeneca AB. Preparation of quinolinecarboxylic acid pyridinylamides as NK3 receptor modulators. WO018465; 2007
42. Astrazeneca AB. Preparation of oxopyridyl quinoline amides as NK3 receptor modulators. WO018469; 2007
43. Astrazeneca AB. Preparation of quinoline derivatives as NK3 antagonists. WO130080; 2006
44. Astrazeneca AB. Preparation of quinolin-3-yl sulfonate esters as NK3 receptor modulators. WO137789; 2006
45. Astrazeneca AB. Preparation of alkylpyridyl quinolines as NK3 receptor modulators. WO018466; 2007
46. Astrazeneca AB. Preparation of 3-(aminomethyl)quinoline-4-carboxamide N-oxides as neurokinin-3 (NK-3) receptor ligands. WO035156; 2007
47. Astrazeneca AB. Preparation of quinolinecarboxyamide derivatives for use as CNS agents. WO115140; 2008
48. Astrazeneca AB. Preparation of alkyl sulfoxide quinolines as Nk-3 receptor ligands. WO035158; 2007
49. Astrazeneca AB. Alkylsulphonamide quinolines. WO069977; 2007
50. Simpson TR, Gadient R, Li Y, et al. Discovery of AZD2624: a potent and selective NK3 antagonist to test the NK3 hypothesis in schizophrenia. Abstracts of Papers, 239th ACS National Meeting; 21 - 25 March 2010: MEDI-35; San Francisco, CA, USA
51. SmithKline Beecham Corp. Preparation of 3-(piperazinylmethyl)-4- quinolinecarboxamides as NK2 and NK3 receptor antagonists. WO000247; 2005
52. SmithKline Beecham Corp. Quinolinecarboxamides having activity at NK3 receptor and their preparations, pharmaceutical compositions and use for treatment of disease mediated by modulation of NK3 receptors. WO050992; 2006
53. SmithKline Beecham Corp. Quinolinecarboxamides having activity at NK3 receptor and their preparations, pharmaceutical compositions and use for treatment of disease mediated by modulation of NK3 receptors. WO050991; 2006
54. SmithKline Beecham Corp. Preparation of 4-quinolinecarboxamides useful for treatment of central nervous system diseases mediated by modulation of the NK3 receptor. WO050989; 2006
55. SmithKline Beecham Corp. Preparation of quinoline-4-carboxamide derivatives as neurokinin 3 receptor antagonists. WO014575; 2005
56. Smith PW, Wyman PA, Lovell P, et al. New quinoline NK3 receptor antagonists with CNS activity. Bioorg Med Chem Lett 2009;19:837-40
57. Dawson LA, Langmead CJ, Dada A, et al. In vitro and in vivo comparison of two non-peptide tachykinin NK3 receptor antagonists: improvements in efficacy achieved through enhanced brain penetration or altered pharmacological characteristics. Eur J Pharmacol 2010;627:106-14
58. SmithKline Beecham Corp. Pyridine derivatives as NK receptor inhibitors and their preparation, pharmaceutical compositions, and use in the treatment of psychotic disorders. WO028654; 2007
59. F. Hoffmann-La Roche AG. Preparation of 2-phenyl-N-(pyridin-3-yl)- Nmethylisobutyramide derivatives as dual NK1/NK3 antagonists for treating schizophrenia. WO002577; 2005
60. Peters J-U, Hoffmann T, Schnider P, et al. Discovery of potent, balanced and orally active dual NK1/NK3 receptor ligands. Bioorg Med Chem Lett 2010;20(11):3405-8
61. SmithKline Beecham Corp. Preparation of crystalline forms of a pyridine derivative. WO015626; 2010
62. Janssen Pharmaceutica NV. (2-Benzyl-4- {4-[1-(tetrahydrofuran-3-carbonyl) - pyrrolidin-3-yl]-piperazin-1-yl}-piperidin- 1-yl)-(3,5-trifluoromethylphenyl)) methanone for the treatment of schizophrenia. WO123081; 2005
63. Janssen Pharmaceutica NV. Preparation of diaza-spiro-[5.5]-undecane derivatives as neurokinin antagonists. WO097795; 2005
64. Janssen Pharmaceutica NV. Preparation of alkyl- and alkanoyl-piperazine derivatives as neurokinin antagonists. WO097774; 2005
65. Janssen Pharmaceutica NV. Substituted oxa-diaza-spiro-[5.5]-undecanone derivatives and their preparation, pharmaceutical compositions and their use as neurokinin antagonists. WO094934; 2006
66. Janssen Pharmaceutica NV. Preparation of diaza-spiro-[4.5]-undecane derivativesas neurokinin antagonists. WO097794; 2005
67. Lundbeck H. A/S. Preparation of 1-phenylcyclopropane-1-carboxamide derivatives as tachykinin NK3 receptor antagonists. WO016884; 2005
68. Lundbeck H. A/S. Isoquinolinone derivatives as NK3 antagonists and their preparation, pharmaceutical compositions and use in the treatment of psychosis and schizophrenia. WO143402; 2009
69. Lundbeck H. A/S. Preparation of isoquinolinone derivatives for use as NK3 antagonists. WO045948; 2010
70. Lundbeck H. A/S. Isoquinolinone derivatives as NK3 antagonists for treatment of psychosis and schizophrenia. WO130240; 2009
71. Lundbeck H. A/S. Isoquinolinone derivatives as NK3 antagonists and their preparation and use in the treatment of psychosis and schizophrenia. WO156339; 2009
72. Lundbeck H. A/S. Preparation of isoquinolinone derivatives for use as NK3 antagonists. WO076016; 2010
73. Lundbeck H. A/S. Preparation of isoquinolinone derivatives for use as NK3 antagonists. WO028655; 2010
74. Merck Sharp & Dohme Ltd. Preparation of heterocyclylmethylquinolinecarboxamides as neurokinin receptor antagonists. WO012900; 2007
75. Merck Sharp & Dohme Ltd. Preparation of substituted quinoline-4-carboxylic hydrazides as NK-2/NK-3 receptor ligands. WO072045; 2004
76. Merck Sharp & Dohme Ltd. Preparation of quinoline-4-carboxylic acid hydrazides as neurokinin receptor antagonists with therapeutic uses. WO120478; 2006
77. Elliott JM, Carling RW, Chambers M, et al. N′,2-Diphenylquinoline- 4- carbohydrazide based NK3 receptor antagonists. Bioorg Med Chem Lett 2006;16:5748-51 (Pubitemid 44508823)
78. Elliott JM, Carling RW, Chicchi GG, et al. N′,2-Diphenylquinoline- 4- carbohydrazide based NK3 receptor antagonists II. Bioorg Med Chem Lett 2006;16:5752-6 (Pubitemid 44508824)
79. Merck Sharp & Dohme Ltd. Preparation of substituted cyclohexyl derivatives as Nk-3 receptor antagonists. WO003965; 2007
80. Pfizer, Inc. Phenylpiperidines as NK1 and NK3 antagonists, their preparation, pharmaceutical compositions and use in the treatment of neurokinin-mediated diseases. WO256164; 2005
81. F. Hoffmann-La Roche AG. Preparation of bistrifluoromethylphenylisobutyric acid pyridinylamides as dual tachykinin NK1/NK3 antagonists for treatment of schizophrenia. WO013050; 2006
82. Hoffmann T, Bos M, Stadler H, et al. Design and synthesis of a novel, achiral class of highly potent and selective, orally active neurokinin-1 receptor antagonists. Bioorg Med Chem Lett 2006;16:1362-5 (Pubitemid 43143023)
83. F. Hoffmann-La Roche AG. Quinazoline derivatives as NK3 receptor antagonists and their preparation and use for the treatment of diseases. WO054968; 2010
84. F. Hoffmann-La Roche AG. Piperazine and [1,4]-diazepan derivatives as neurokinin antagonists and their preparation. WO151969; 2008
85. F. Hoffmann-La Roche AG. Preparation of piperidine derivatives as NK3 receptor antagonists. WO033995; 2009
86. F. Hoffmann-La Roche AG. Preparation of spiropiperidine derivatives as antagonists of neurokinin 3 receptors. WO081012; 2008
87. F. Hoffmann-La Roche AG. Preparation of prolinamide derivatives as NK3 antagonists. WO148689; 2008
88. F. Hoffmann-La Roche AG. Preparation of prolinamide-tetrazole derivatives, particularly 1-[[(2S,4S)-4-(5-phenyl-2Htetrazol- 2-yl)pyrrolidin-2-yl]carbonyl] piperazines, as NK3 antagonists. WO148688; 2008
89. F. Hoffmann-La Roche AG. Pyrrolidine derivatives as dual NK1/NK3 receptor antagonists and their preparation, pharmaceutical compositions and use in the treatment of schizophrenia. WO128891; 2008
90. Ratni H, Ballard TM, Bissantz C, et al. Rational design of novel pyrrolidine derivatives as orally active neurokinin-3 receptor antagonists. Bioorg Med Chem Lett 2010;20:6735-8
91. F. Hoffmann-La Roche AG. N-Benzyl pyrrolidinamine derivatives as NK-3 receptor antagonists and their preparation and use in the treatment of diseases. WO040663; 2010
92. Hoffmann-La Roche AG. Preparation of N-benzyl pyrrolidinamine derivatives as neurokinin-3 receptor antagonists and their use in the treatment of diseases. WO113424; 2010
93. F. Hoffmann-La Roche AG. Pyrrolidine-(hetero)aryl ether derivatives as NK3 receptor antagonists and their preparation, pharmaceutical compositions and use in the treatment of diseases. WO019163; 2009
94. F. Hoffmann-La Roche AG. Pyrrolidine aryl-ether as NK3 receptor antagonists, their preparation, and pharmaceutical applications. WO024502; 2009
95. F. Hoffmann-La Roche AG. Preparation of pyridinyloxyethyl pyrrolidinyl piperidinyl methanones and related compounds as neurokinin NK3 receptor antagonists. WO306043; 2009
96. F. Hoffmann-La Roche AG. Preparation of phenylpiperidine derivatives for use as NK-3 receptor antagonists. WO086259; 2010
97. F. Hoffmann-La Roche AG. Piperidine derivatives as nk3 receptor antagonists. WO106081; 2010
98. Neurogen Corp. Preparation of diaryl imidazoles as neurokinin-3 receptor modulators. US148601; 2005
99. Neurogen Corp. Preparation of diaryl pyrazoles as neurokinin-3 receptor modulators. WO061462; 2005
100. Solvay Pharmaceuticals G.m.b.H. Piperidinamines as dual NK2/NK3-antagonists, pharmaceutical compositions comprising them and processes for their preparations and use in the treatment of diseases WO088181; 2007
101. Takeda Pharmaceutical Co., Ltd. Nitrogen-containing heterocyclic compounds as tachykinin receptor antagonists and their preparation and use in the treatment of diseases WO072643; 2009
102. Takeda Pharmaceutical Co., Ltd. Preparation of nitrogen-containing heterocyclic compounds as tachykinin receptor antagonistsWO032856; 2010
103. GSK. 2010; Available from: . gsk.com/investors/product-pipeline/docs/ GSK-product-pipeline-Feb-2010.pdf. [Cited]
104. Krajewski SJ, Anderson MJ, Iles-Shih L, et al. Morphologic evidence that neurokinin B modulatesgonadotropin-releasing hormone secretion via neurokinin 3 receptors in the rat median eminence. J Comp Neurol 2005;489:372-86 (Pubitemid 41026235)
105. Sandoval-Guzman T, Rance NE. Central injection of senktide, an NK3 receptor agonist, or neuropeptide Y inhibits LH secretion and induces different patterns of Fos expression in the rat hypothalamus. Brain Res 2004;1026:307-12 (Pubitemid 39361561)
106. Topaloglu AK, Reimann F, Guclu M, et al. TAC3 and TACR3 mutations in familial hypogonadotropic hypogonadism reveal a key role for Neurokinin B in the central control of reproduction. Nat Genet 2009;41:354-8
107. Ramaswamy S, Seminara SB, Ali B, et al. Neurokinin B stimulates GnRH release in the male monkey (Macaca mulatta) and is colocalized with kisspeptin in the arcuate nucleus. Endocrinology 2010;151:4494-503
108. SmithKline Beecham Corp. Anti-androgens and methods for treating disease. WO43008; 2000
109. Schering Corp. The use of neurokinin receptor antagonists to treat androgen-dependent diseases. WO089802; 2002
110. Losco PE, Leach MW, Sinha D, et al. Administration of an antagonist of neurokinin receptors 1, 2, and 3 results in reproductive tract changes in beagle dogs, but not rats. Toxicol Pathol 2007;35:310-22 (Pubitemid 46393078)
111. Houghton LA, Cremonini F, Camilleri M, et al. Effect of the NK (3) receptor antagonist, talnetant, on rectal sensory function and compliance in healthy humans. Neurogastroenterol Motil 2007;19:732-43 (Pubitemid 47312398)
112. Engel JB, Schally AV. Drug insight: clinical use of agonists and antagonists of luteinizing-hormone-releasing hormone. Nat Clin Pract Endocrinol Metab 2007;3:157-67 (Pubitemid 46146968)
113. Akaza H. Future prospects for luteinizing hormone-releasing hormone analogues in prostate cancer treatment. Pharmacology 2010;85:110-20
114. Hackshaw A. Luteinizing hormone-releasing hormone (LHRH) agonists in the treatment of breast cancer. Expert Opin Pharmacother 2009;10:2633-9
115. Rance NE, Krajewski SJ, Smith MA, et al. Neurokinin B and the hypothalamic regulation of reproduction. Brain Res 2010;2010:116-28
116. Ballesteros JA, Weinstein H. Integrated methods for construction three-dimensional models and computational probing of structure-function relations in G protein-coupled receptors. Methods Neurosci 1995;25:366-428