SCOPUS 정보 검색 플랫폼

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 20, 2012, Pages 6454-6459

Discovery of 1H-pyrrolo[2,3-c]pyridine-7-carboxamides as novel, allosteric mGluR5 antagonists

(8) Koller, Manuel a Carcache, David A a Orain, David a Ertl, Peter a Behnke, Dirk a Desrayaud, Sandrine a Laue, Grit a Vranesic, Ivo a

a NOVARTIS PHARMA AG (Switzerland)

Author keywords

1H pyrrolo 2,3 c pyridine 7 carboxamides; Excitatory amino acid; Glutamate; Metabotropic glutamate receptor; mGluR5; Negative allosteric modulator

Indexed keywords

1H PYRROLO[2,3 C]PYRIDINE 7 CARBOXAMIDE; METABOTROPIC GLUTAMATE RECEPTOR 5 ANTAGONIST; METABOTROPIC RECEPTOR 5; METABOTROPIC RECEPTOR ANTAGONIST; UNCLASSIFIED DRUG;

ALLOSTERISM; AQUEOUS SOLUTION; ARTICLE; DRUG CONFORMATION; DRUG POTENCY; DRUG SOLUBILITY; DRUG SYNTHESIS; HYDROGEN BOND; IC 50; IN VITRO STUDY; LIPOPHILICITY; NONHUMAN; PHYSICAL CHEMISTRY; PKA; RAT; SOLVATION;

ALLOSTERIC REGULATION; AMIDES; DRUG DISCOVERY; HUMANS; INHIBITORY CONCENTRATION 50; PYRIDONES; PYRROLES; RECEPTORS, METABOTROPIC GLUTAMATE; SOLUBILITY;

EID: 84866739273 PISSN: 0960894X EISSN: 14643405 Source Type: Journal
DOI: 10.1016/j.bmcl.2012.08.053 Document Type: Article

Times cited : (9)

References (25)

1
- 0029872230
- C. Romano, A.N. van den Pol, and K.L. OMalley J. Comp. Neurol. 367 1996 403
- (1996) J. Comp. Neurol. , vol.367 , pp. 403
- Romano, C.¹ Van Den Pol, A.N.² Omalley, K.L.³

2
- 79952021183
- M. Julio-Pieper, P.J. Flor, T.G. Dinan, and J.F. Cryan Pharmacol. Rev. 63 2011 35
- (2011) Pharmacol. Rev. , vol.63 , pp. 35
- Julio-Pieper, M.¹ Flor, P.J.² Dinan, T.G.³ Cryan, J.F.⁴

3
- 84858283586
- W.O. Rohof, E. Aronica, H. Beaumont, D. Troost, and G.E. Boeckxstaens Neurogastroenterol. Motil. 24 2012 383
- (2012) Neurogastroenterol. Motil. , vol.24 , pp. 383
- Rohof, W.O.¹ Aronica, E.² Beaumont, H.³ Troost, D.⁴ Boeckxstaens, G.E.⁵

4
- 84856078399
- C. Gross, E.M. Berry-Kravis, and G.J. Bassell Neuropsychopharmacol. Rev. 37 2012 178
- (2012) Neuropsychopharmacol. Rev. , vol.37 , pp. 178
- Gross, C.¹ Berry-Kravis, E.M.² Bassell, G.J.³

5
- 79959372108
- D. Berg, J. Godau, C. Trenkwalder, K. Eggert, I. Csoti, A. Storch, H. Huber, M. Morelli-Canelo, M. Stamelou, V. Ries, M. Wolz, C. Schneider, T. Di Paolo, F. Gasparini, S. Hariry, M. Vandemeulebroecke, W. Abi-Saab, K. Cooke, D. Johns, and B. Gomez-Mancilla Mov. Disord. 26 2011 1243
- (2011) Mov. Disord. , vol.26 , pp. 1243
- Berg, D.¹ Godau, J.² Trenkwalder, C.³ Eggert, K.⁴ Csoti, I.⁵ Storch, A.⁶ Huber, H.⁷ Morelli-Canelo, M.⁸ Stamelou, M.⁹ Ries, V.¹⁰ Wolz, M.¹¹ Schneider, C.¹² Di Paolo, T.¹³ Gasparini, F.¹⁴ Hariry, S.¹⁵ Vandemeulebroecke, M.¹⁶ Abi-Saab, W.¹⁷ Cooke, K.¹⁸ Johns, D.¹⁹ Gomez-Mancilla, B.²⁰ more..

6
- 63449091016
- C. Keywood, and M. Wakefield Neuropharmacology 55 2008 605
- (2008) Neuropharmacology , vol.55 , pp. 605
- Keywood, C.¹ Wakefield, M.²

7
- 40749139454
- G. Jaeschke, J.G. Wettstein, R.E. Nordquist, and W. Spooren Expert Opin. Ther. Patents 18 2008 123
- (2008) Expert Opin. Ther. Patents , vol.18 , pp. 123
- Jaeschke, G.¹ Wettstein, J.G.² Nordquist, R.E.³ Spooren, W.⁴

8
- 79952787066
- F. Zerbib, S. Bruley des Varannes, S. Roman, R. Tutuian, J.-P. Galmiche, F. Mion, J. Tack, P. Malfertheiner, and C. Keywood Aliment. Pharmacol. Ther. 33 2011 911
- (2011) Aliment. Pharmacol. Ther. , vol.33 , pp. 911
- Zerbib, F.¹ Bruley Des Varannes, S.² Roman, S.³ Tutuian, R.⁴ Galmiche, J.-P.⁵ Mion, F.⁶ Tack, J.⁷ Malfertheiner, P.⁸ Keywood, C.⁹

9
- 34347241277
- A. Palucha, and A. Pilc Pharmacol. Ther. 115 2007 116
- (2007) Pharmacol. Ther. , vol.115 , pp. 116
- Palucha, A.¹ Pilc, A.²

10
- 80053505880
- M.C. Montana, and R.W. Gereau Curr. Pharmaceutical Biotech. 12 2011 1681
- (2011) Curr. Pharmaceutical Biotech. , vol.12 , pp. 1681
- Montana, M.C.¹ Gereau, R.W.²

11
- 84971012261
- C.W. Lindsley, B.S. Bates, U.N. Menon, S.B. Jadhav, A.S. Kane, C.K. Jones, A.L. Rodriguez, P.J. Conn, C.M. Olson, D.G. Winder, and K.A. Emmitte ACS Chem. Neurosci. 2 2011 471
- (2011) ACS Chem. Neurosci. , vol.2 , pp. 471
- Lindsley, C.W.¹ Bates, B.S.² Menon, U.N.³ Jadhav, S.B.⁴ Kane, A.S.⁵ Jones, C.K.⁶ Rodriguez, A.L.⁷ Conn, P.J.⁸ Olson, C.M.⁹ Winder, D.G.¹⁰ Emmitte, K.A.¹¹

12
- 16244380185
- C. Bonnefous, J.-M. Vernier, J.H. Hutchinson, J. Chung, G. Reyes-Manalo, and T. Kamenecka Bioorg. Med. Chem. Lett. 15 2005 1197
- (2005) Bioorg. Med. Chem. Lett. , vol.15 , pp. 1197
- Bonnefous, C.¹ Vernier, J.-M.² Hutchinson, J.H.³ Chung, J.⁴ Reyes-Manalo, G.⁵ Kamenecka, T.⁶

13
- 33846901189
- S.M. Ceccarelli, G. Jaeschke, B. Buettelmann, J. Huwyler, S. Kolczewski, J.-U. Peters, E. Prinssen, R. Porter, W. Spooren, and E. Vieira Bioorg. Med. Chem. Lett. 17 2007 1302
- (2007) Bioorg. Med. Chem. Lett. , vol.17 , pp. 1302
- Ceccarelli, S.M.¹ Jaeschke, G.² Buettelmann, B.³ Huwyler, J.⁴ Kolczewski, S.⁵ Peters, J.-U.⁶ Prinssen, E.⁷ Porter, R.⁸ Spooren, W.⁹ Vieira, E.¹⁰

14
- 0028070806
- For other examples of phenole/pyrrole bioisosterism see e.g.
- For other examples of phenole/pyrrole bioisosterism see e.g. A. Leonardi, C. Riva, C. De Toma, C. Boi, R. Pennini, and G. Sironi Eur. J. Med. Chem. 29 1994 551
- (1994) Eur. J. Med. Chem. , vol.29 , pp. 551
- Leonardi, A.¹ Riva, C.² De Toma, C.³ Boi, C.⁴ Pennini, R.⁵ Sironi, G.⁶

15
- 33845307270
- S. Hintermann, I. Vranesic, H. Allgeier, A. Brülisauer, D. Hoyer, M. Lemaire, T. Moenius, S. Urwyler, S. Whitebread, F. Gasparini, and Y.P. Auberson Bioorg. Med. Chem. 15 2007 903
- (2007) Bioorg. Med. Chem. , vol.15 , pp. 903
- Hintermann, S.¹ Vranesic, I.² Allgeier, H.³ Brülisauer, A.⁴ Hoyer, D.⁵ Lemaire, M.⁶ Moenius, T.⁷ Urwyler, S.⁸ Whitebread, S.⁹ Gasparini, F.¹⁰ Auberson, Y.P.¹¹

16
- 0034721795
- A. Pagano, D. Rüegg, S. Litschig, N. Stoehr, C. Stierlin, M. Heinrich, P. Floersheim, L. Prezèau, F. Carroll, J.-P. Pin, A. Cambria, I. Vranesic, P.J. Flor, F. Gasparini, and R. Kuhn J. Biol. Chem. 275 2000 33750
- (2000) J. Biol. Chem. , vol.275 , pp. 33750
- Pagano, A.¹ Rüegg, D.² Litschig, S.³ Stoehr, N.⁴ Stierlin, C.⁵ Heinrich, M.⁶ Floersheim, P.⁷ Prezèau, L.⁸ Carroll, F.⁹ Pin, J.-P.¹⁰ Cambria, A.¹¹ Vranesic, I.¹² Flor, P.J.¹³ Gasparini, F.¹⁴ Kuhn, R.¹⁵

17
- 0024583123
- G. Bartoli, G. Palmieri, M. Bosco, and R. Dalpozzo Tetrahedron Lett. 30 1989 2129
- (1989) Tetrahedron Lett. , vol.30 , pp. 2129
- Bartoli, G.¹ Palmieri, G.² Bosco, M.³ Dalpozzo, R.⁴

18
- 84866741640
- U.S. Patent 185,154
- Kuehne, H.; Luebbers, T.; Mattei, P.; Maugeais, C.; Pflieger, P.; Scalone, M. U.S. Patent 185,154, 2007.
- (2007)
- Kuehne, H.¹ Luebbers, T.² Mattei, P.³ Maugeais, C.⁴ Pflieger, P.⁵ Scalone, M.⁶

19
- 84875004990
- 1H NMR and UPLC/MS data of the test compounds are reported in Supplementary data
- 1H NMR and UPLC/MS data of the test compounds are reported in Supplementary data.

20
- 0035138216
- N. Jain, and S.H. Yalkowsky J. Pharmaceutical Sci. 90 2001 234
- (2001) J. Pharmaceutical Sci. , vol.90 , pp. 234
- Jain, N.¹ Yalkowsky, S.H.²

21
- 79952804851
- M. Ishikawa, and Y. Hashimoto J. Med. Chem. 54 2011 1539
- (2011) J. Med. Chem. , vol.54 , pp. 1539
- Ishikawa, M.¹ Hashimoto, Y.²

22
- 0034461768
- C.A. Lipinsky J. Pharmacol. Toxicol. Methods 44 2000 235
- (2000) J. Pharmacol. Toxicol. Methods , vol.44 , pp. 235
- Lipinsky, C.A.¹

23
- 0029144222
- Experimental setup based on
- Experimental setup based on L.P. Daggett, A.I. Sacaan, M. Akong, S.P. Rao, S.D. Hess, C. Liaw, A. Urrutia, C. Jachec, S.B. Ellis, J. Dreessen, T. Knöpfel, G.B. Landwehrmeyer, C.M. Testa, A.B. Young, M. Varney, E.C. Johnson, and G. Veliçelebi Neuropharmacology 34 1995 871
- (1995) Neuropharmacology , vol.34 , pp. 871
- Daggett, L.P.¹ Sacaan, A.I.² Akong, M.³ Rao, S.P.⁴ Hess, S.D.⁵ Liaw, C.⁶ Urrutia, A.⁷ Jachec, C.⁸ Ellis, S.B.⁹ Dreessen, J.¹⁰ Knöpfel, T.¹¹ Landwehrmeyer, G.B.¹² Testa, C.M.¹³ Young, A.B.¹⁴ Varney, M.¹⁵ Johnson, E.C.¹⁶ Veliçelebi, G.¹⁷

24
- 0034597613
- M.H. Norman, N. Chen, Z. Chen, C. Fotsch, C. Hale, N. Han, R. Hurt, T. Jenkins, J. Kincaid, L. Liu, Y. Lu, O. Moreno, V.J. Santora, J.D. Sonnenberg, and W. Karbon J. Med. Chem. 43 2000 4288
- (2000) J. Med. Chem. , vol.43 , pp. 4288
- Norman, M.H.¹ Chen, N.² Chen, Z.³ Fotsch, C.⁴ Hale, C.⁵ Han, N.⁶ Hurt, R.⁷ Jenkins, T.⁸ Kincaid, J.⁹ Liu, L.¹⁰ Lu, Y.¹¹ Moreno, O.¹² Santora, V.J.¹³ Sonnenberg, J.D.¹⁴ Karbon, W.¹⁵

25
- 84864409984
- B. Davies, and T. Morris Pharmaceutical Res. 1093 1993 10
- (1993) Pharmaceutical Res. , vol.1093 , pp. 10
- Davies, B.¹ Morris, T.²

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.