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Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 18, 2011, Pages 5310-5314

Strategies to lower the Pgp efflux liability in a series of potent indole azetidine MCHR1 antagonists

(11) Lu, Kai a Jiang, Yu a Chen, Bin a Eldemenky, Eman M a Ma, Gil a Packiarajan, Mathivanan a Chandrasena, Gamini a White, Andrew D a Jones, Kenneth A a Li, Boshan a Hong, Sang Phyo a

a LUNDBECK RESEARCH USA (United States)

Author keywords

CNS penetration; Dihydroindolyl azetidine; Indolyl azetidine; MCH; Pgp

Indexed keywords

AZETIDINE DERIVATIVE; GLYCOPROTEIN P; INDOLE DERIVATIVE; MELANIN CONCENTRATING HORMONE RECEPTOR 1 ANTAGONIST;

ARTICLE; BINDING AFFINITY; CENTRAL NERVOUS SYSTEM; DRUG CONFORMATION; DRUG PENETRATION; DRUG SYNTHESIS; HYDROGEN BOND; PROTEIN TRANSPORT;

ANIMALS; AZETIDINES; HYDROGEN BONDING; INDOLES; MICE; MICE, KNOCKOUT; MOLECULAR STRUCTURE; P-GLYCOPROTEIN; RATS; RECEPTORS, SOMATOSTATIN; STEREOISOMERISM;

EID: 80051945851 PISSN: 0960894X EISSN: 14643405 Source Type: Journal
DOI: 10.1016/j.bmcl.2011.07.020 Document Type: Article

Times cited : (13)

References (30)

1
- 0020643565
- H. Kawauchi, I. Kawazoe, M. Tsubokawa, M. Kishida, and B.I. Baker Nature 305 1983 321
- (1983) Nature , vol.305 , pp. 321
- Kawauchi, H.¹ Kawazoe, I.² Tsubokawa, M.³ Kishida, M.⁴ Baker, B.I.⁵

2
- 0026766094
- J.C. Bittencourt, F. Presse, C. Arias, C. Peto, J. Vaughan, J.L. Nahon, W. Vale, and P.E. Sawchenko J. Comp. Neurol. 319 1992 218
- (1992) J. Comp. Neurol. , vol.319 , pp. 218
- Bittencourt, J.C.¹ Presse, F.² Arias, C.³ Peto, C.⁴ Vaughan, J.⁵ Nahon, J.L.⁶ Vale, W.⁷ Sawchenko, P.E.⁸

3
- 0035912663
- S. An, G. Cutler, J.J. Zhao, S. Huang, H. Tian, W. Li, L. Liang, M. Rich, A. Bakleh, J. Du, J. Chen, and K. Dal Proc. Natl. Acad. Sci. 98 2001 7576
- (2001) Proc. Natl. Acad. Sci. , vol.98 , pp. 7576
- An, S.¹ Cutler, G.² Zhao, J.J.³ Huang, S.⁴ Tian, H.⁵ Li, W.⁶ Liang, L.⁷ Rich, M.⁸ Bakleh, A.⁹ Du, J.¹⁰ Chen, J.¹¹ Dal, K.¹²

4
- 13344279395
- D. Qu, D.S. Ludwig, S. Gammeltoft, M. Piper, M.A. Pelleymounter, M.J. Cullen, W.F. Mathes, R. Przypek, R. Kanarek, and E. Maratos-Flier Nature 380 1996 243
- (1996) Nature , vol.380 , pp. 243
- Qu, D.¹ Ludwig, D.S.² Gammeltoft, S.³ Piper, M.⁴ Pelleymounter, M.A.⁵ Cullen, M.J.⁶ Mathes, W.F.⁷ Przypek, R.⁸ Kanarek, R.⁹ Maratos-Flier, E.¹⁰

5
- 0022003012
- B.I. Baker, D.J. Bird, and J.C. Buckingham J. Endocrinol. 106 1985 R5
- (1985) J. Endocrinol. , vol.106 , pp. 5
- Baker, B.I.¹ Bird, D.J.² Buckingham, J.C.³

6
- 0041828556
- G. Hervieu Expert Opin. Ther. Targets 7 2003 495
- (2003) Expert Opin. Ther. Targets , vol.7 , pp. 495
- Hervieu, G.¹

7
- 0036797774
- O. Della-Zuana, F. Presse, C. Ortola, J. Duhault, J.L. Nahon, and N. Levens Int. J. Obes. 26 2002 1289
- (2002) Int. J. Obes. , vol.26 , pp. 1289
- Della-Zuana, O.¹ Presse, F.² Ortola, C.³ Duhault, J.⁴ Nahon, J.L.⁵ Levens, N.⁶

8
- 0037369253
- A. Gomori, A. Ishihara, M. Ito, S. Mashiko, H. Matsushita, M. Yumoto, M. Ito, T. Tanaka, S. Tokita, M. Moriya, H. Iwaasa, and A. Kanatani Am. J. Physiol. Edocrinol. Metab. 284 2003 E583
- (2003) Am. J. Physiol. Edocrinol. Metab. , vol.284 , pp. 583
- Gomori, A.¹ Ishihara, A.² Ito, M.³ Mashiko, S.⁴ Matsushita, H.⁵ Yumoto, M.⁶ Ito, M.⁷ Tanaka, T.⁸ Tokita, S.⁹ Moriya, M.¹⁰ Iwaasa, H.¹¹ Kanatani, A.¹²

9
- 0032542294
- M. Shimada, N.A. Tritos, B.B. Lowell, J.S. Flier, and E. Maratos-Flier Nature 396 1998 670
- (1998) Nature , vol.396 , pp. 670
- Shimada, M.¹ Tritos, N.A.² Lowell, B.B.³ Flier, J.S.⁴ Maratos-Flier, E.⁵

10
- 0037022667
- D.J. Marsh, D.T. Weingarth, D.E. Novi, H.Y. Chen, M.E. Trunbauer, A.S. Chen, X.M. Guan, M.M. Jiang, Y. Feng, R.E. Camacho, Z. Shen, E.G. Frazier, H. Yu, J.M. Metzger, S.J. Kuca, L.P. Shearman, S. Gopal-Truter, D.J. MacNeil, A.M. Strack, D.E. Maclyntyre, L.H. Van der Ploeg, and S. Qian Proc. Natl. Acad. Sci. 99 2002 3240
- (2002) Proc. Natl. Acad. Sci. , vol.99 , pp. 3240
- Marsh, D.J.¹ Weingarth, D.T.² Novi, D.E.³ Chen, H.Y.⁴ Trunbauer, M.E.⁵ Chen, A.S.⁶ Guan, X.M.⁷ Jiang, M.M.⁸ Feng, Y.⁹ Camacho, R.E.¹⁰ Shen, Z.¹¹ Frazier, E.G.¹² Yu, H.¹³ Metzger, J.M.¹⁴ Kuca, S.J.¹⁵ Shearman, L.P.¹⁶ Gopal-Truter, S.¹⁷ MacNeil, D.J.¹⁸ Strack, A.M.¹⁹ MacLyntyre, D.E.²⁰ Van Der Ploeg, L.H.²¹ Qian, S.²² more..

11
- 18444375866
- Y. Chen, C. Hu, C.K. Hsu, Q. Zhang, C. Bi, M. Asnicar, H.M. Hsiung, N. Fox, M.J. Slieker, D.D. Yang, M.L. Heiman, and Y. Shi Endocrinology 143 2002 2469
- (2002) Endocrinology , vol.143 , pp. 2469
- Chen, Y.¹ Hu, C.² Hsu, C.K.³ Zhang, Q.⁴ Bi, C.⁵ Asnicar, M.⁶ Hsiung, H.M.⁷ Fox, N.⁸ Slieker, M.J.⁹ Yang, D.D.¹⁰ Heiman, M.L.¹¹ Shi, Y.¹²

12
- 0036341292
- B. Borowsky, M.M. Durkin, K. Ogozalek, M.R. Marzabadi, J. DeLeon, R. Heurich, H. Lichtblau, Z. Shaposhnik, I. Daniewska, T.P. Blackburn, T.A. Branchek, C. Gerald, P.J. Vaysse, and C. Forray Nat. Med. 8 2002 825
- (2002) Nat. Med. , vol.8 , pp. 825
- Borowsky, B.¹ Durkin, M.M.² Ogozalek, K.³ Marzabadi, M.R.⁴ Deleon, J.⁵ Heurich, R.⁶ Lichtblau, H.⁷ Shaposhnik, Z.⁸ Daniewska, I.⁹ Blackburn, T.P.¹⁰ Branchek, T.A.¹¹ Gerald, C.¹² Vaysse, P.J.¹³ Forray, C.¹⁴

13
- 20944435410
- S. Chaki, T. Funakoshi, S. Hirota-Okuno, M. Nishiguchi, T. Shimazaki, M. Iijima, A.J. Grottick, K. Kanuma, K. Omodera, K. Modera, Y. Sekiguchi, S. Okuyama, T.A. Tran, G. Semple, and W. Thomsen J. Pharmacol. Exp. Ther. 313 2005 831
- (2005) J. Pharmacol. Exp. Ther. , vol.313 , pp. 831
- Chaki, S.¹ Funakoshi, T.² Hirota-Okuno, S.³ Nishiguchi, M.⁴ Shimazaki, T.⁵ Iijima, M.⁶ Grottick, A.J.⁷ Kanuma, K.⁸ Omodera, K.⁹ Modera, K.¹⁰ Sekiguchi, Y.¹¹ Okuyama, S.¹² Tran, T.A.¹³ Semple, G.¹⁴ Thomsen, W.¹⁵

14
- 34548078784
- Y. Jiang, C.A. Chen, K. Lu, I. Daniewska, J. De Leon, R. Kong, C. Forray, B. Li, L.G. Hegde, T.D. Wolinsky, D.A. Craig, J.M. Wetzel, K. Anderson, and M.R. Marzabadi J. Med. Chem. 50 2007 3870
- (2007) J. Med. Chem. , vol.50 , pp. 3870
- Jiang, Y.¹ Chen, C.A.² Lu, K.³ Daniewska, I.⁴ De Leon, J.⁵ Kong, R.⁶ Forray, C.⁷ Li, B.⁸ Hegde, L.G.⁹ Wolinsky, T.D.¹⁰ Craig, D.A.¹¹ Wetzel, J.M.¹² Anderson, K.¹³ Marzabadi, M.R.¹⁴

15
- 34548063834
- C.A. Chen, Y. Jiang, K. Lu, I. Daniewska, C.G. Mazza, L. Negron, C. Forray, T. Parola, B. Li, L.G. Hegde, T.D. Wolinsky, D.A. Craig, R. Kong, J.M. Wetzel, K. Anderson, and M.R. Marbabadi J. Med. Chem. 50 2007 3883
- (2007) J. Med. Chem. , vol.50 , pp. 3883
- Chen, C.A.¹ Jiang, Y.² Lu, K.³ Daniewska, I.⁴ Mazza, C.G.⁵ Negron, L.⁶ Forray, C.⁷ Parola, T.⁸ Li, B.⁹ Hegde, L.G.¹⁰ Wolinsky, T.D.¹¹ Craig, D.A.¹² Kong, R.¹³ Wetzel, J.M.¹⁴ Anderson, K.¹⁵ Marbabadi, M.R.¹⁶

16
- 20144379914
- A.J. Sourers, J. Gao, M. Brune, E. Bush, D. Wodka, A. Vasudevan, A.S. Judd, M. Mulhern, S. Brodjian, B. Dayton, R. Shapiro, L.E. Hernandez, K.C. Mash, H.L. Sham, C.A. Collins, and P.R. Kym J. Med. Chem. 48 2005 1318
- (2005) J. Med. Chem. , vol.48 , pp. 1318
- Sourers, A.J.¹ Gao, J.² Brune, M.³ Bush, E.⁴ Wodka, D.⁵ Vasudevan, A.⁶ Judd, A.S.⁷ Mulhern, M.⁸ Brodjian, S.⁹ Dayton, B.¹⁰ Shapiro, R.¹¹ Hernandez, L.E.¹² Mash, K.C.¹³ Sham, H.L.¹⁴ Collins, C.A.¹⁵ Kym, P.R.¹⁶

17
- 38949111737
- S.D. Erickson, B. Banner, S. Berthel, K. Conde-Knape, F. Falcioni, I. Hakimi, B. Hennessy, R.F. Kester, K. Kim, C. Ma, W. McComas, F. Mennona, S. Mischke, L. Orzechowski, Y. Qian, H. Salari, J. Tengi, K. Thakkar, R. Taub, J.W. Tilley, and H. Wang Bioorg. Med. Chem. Lett. 18 2008 1402
- (2008) Bioorg. Med. Chem. Lett. , vol.18 , pp. 1402
- Erickson, S.D.¹ Banner, B.² Berthel, S.³ Conde-Knape, K.⁴ Falcioni, F.⁵ Hakimi, I.⁶ Hennessy, B.⁷ Kester, R.F.⁸ Kim, K.⁹ Ma, C.¹⁰ McComas, W.¹¹ Mennona, F.¹² Mischke, S.¹³ Orzechowski, L.¹⁴ Qian, Y.¹⁵ Salari, H.¹⁶ Tengi, J.¹⁷ Thakkar, K.¹⁸ Taub, R.¹⁹ Tilley, J.W.²⁰ Wang, H.²¹ more..

18
- 65149100300
- T. Suzuki, M. Moriya, T. Sakamoto, T. Suga, H. Kishino, H. Takahashi, M. Ishikawa, K. Nagai, Y. Imai, E. Sekino, M. Ito, H. Iwaasa, A. Ishihara, S. Tokita, A. Kanatani, N. Sato, and T. Fukami Bioorg. Med. Chem. Lett. 19 2009 3072
- (2009) Bioorg. Med. Chem. Lett. , vol.19 , pp. 3072
- Suzuki, T.¹ Moriya, M.² Sakamoto, T.³ Suga, T.⁴ Kishino, H.⁵ Takahashi, H.⁶ Ishikawa, M.⁷ Nagai, K.⁸ Imai, Y.⁹ Sekino, E.¹⁰ Ito, M.¹¹ Iwaasa, H.¹² Ishihara, A.¹³ Tokita, S.¹⁴ Kanatani, A.¹⁵ Sato, N.¹⁶ Fukami, T.¹⁷

19
- 77956176750
- P.K. Sasmal, S. Sasmal, P.T. Rao, B. Venkatesham, M. Roshaiah, C. Abbineni, I. Khanna, V.P. Jadhav, J. Suresh, R. Talwar, S. Muzeeb, J. Receveur, T.M. Frimurer, O. Rist, L. Elster, and T. Hoegberg Bioorg. Med. Chem. Lett. 20 2010 5443
- (2010) Bioorg. Med. Chem. Lett. , vol.20 , pp. 5443
- Sasmal, P.K.¹ Sasmal, S.² Rao, P.T.³ Venkatesham, B.⁴ Roshaiah, M.⁵ Abbineni, C.⁶ Khanna, I.⁷ Jadhav, V.P.⁸ Suresh, J.⁹ Talwar, R.¹⁰ Muzeeb, S.¹¹ Receveur, J.¹² Frimurer, T.M.¹³ Rist, O.¹⁴ Elster, L.¹⁵ Hoegberg, T.¹⁶

20
- 0028292927
- J. Warmake, and B. Ganetzky Proc. Natl. Acad. Sci. 91 1994 3438
- (1994) Proc. Natl. Acad. Sci. , vol.91 , pp. 3438
- Warmake, J.¹ Ganetzky, B.²

21
- 33645317063
- M. Sanguinetti, and M. Tristani-Fioruzi Nature 440 2006 463
- (2006) Nature , vol.440 , pp. 463
- Sanguinetti, M.¹ Tristani-Fioruzi, M.²

22
- 38749087222
- Experimental details are provided in Supplementary data
- B. Feng, J.B. Mills, R.E. Davidson, R.J. Mireles, J.S. Janiszewski, M.D. Troutman, and S.M. de Morais Drug Metab. Dispos. 36 2008 268 Experimental details are provided in Supplementary data
- (2008) Drug Metab. Dispos. , vol.36 , pp. 268
- Feng, B.¹ Mills, J.B.² Davidson, R.E.³ Mireles, R.J.⁴ Janiszewski, J.S.⁵ Troutman, M.D.⁶ De Morais, S.M.⁷

23
- 84855686139
- -6 cm/s (pH 7.4-3.0)
- -6 cm/s (pH 7.4-3.0).

24
- 1842535990
- R. Didziapetris, P. Japertas, A. Avdeef, and A. Petrauskas J. Drug Target. 11 2003 391
- (2003) J. Drug Target. , vol.11 , pp. 391
- Didziapetris, R.¹ Japertas, P.² Avdeef, A.³ Petrauskas, A.⁴

25
- 37249023309
- a value calculated by the program Moka. See also
- a value calculated by the program Moka. See also: F. Milletti, L. Storchi, G. Sforna, and G. Cruciani J. Chem. Inf. Model. 47 2007 2172
- (2007) J. Chem. Inf. Model. , vol.47 , pp. 2172
- Milletti, F.¹ Storchi, L.² Sforna, G.³ Cruciani, G.⁴

26
- 0037194617
- J.S. Albert, D. Aharony, D. Andisik, H. Barthlow, P.R. Bernstein, R.A. Bialecki, R. Dedinas, B.T. Dembofsky, D. Hill, K. Kirkland, G.M. Koether, B.J. Kosmider, C. Ohnmacht, W. Palmer, W. Potts, W. Rumsey, L. Shen, A. Shenvi, S. Sherwood, P.J. Warwick, and K. Russell J. Med. Chem. 45 2002 3972
- (2002) J. Med. Chem. , vol.45 , pp. 3972
- Albert, J.S.¹ Aharony, D.² Andisik, D.³ Barthlow, H.⁴ Bernstein, P.R.⁵ Bialecki, R.A.⁶ Dedinas, R.⁷ Dembofsky, B.T.⁸ Hill, D.⁹ Kirkland, K.¹⁰ Koether, G.M.¹¹ Kosmider, B.J.¹² Ohnmacht, C.¹³ Palmer, W.¹⁴ Potts, W.¹⁵ Rumsey, W.¹⁶ Shen, L.¹⁷ Shenvi, A.¹⁸ Sherwood, S.¹⁹ Warwick, P.J.²⁰ Russell, K.²¹ more..

27
- 80051949729
- Note
- 2O (see also Supplementary data).

28
- 80051916398
- Difluorination of the phenyl group also did not improve CNS exposure relative to 5a
- Difluorination of the phenyl group also did not improve CNS exposure relative to 5a.

29
- 34247379910
- C. Cox, M. Breslin, D. Whitman, P. Coleman, R. Garbaccio, M. Fraley, M. Zrada, C. Buser, E. Walsh, K. Mamilton, R. Lobell, W. Tao, M. Abrams, V. South, H. Huber, N. Kohl, and G. Hartman Bioorg. Med. Chem. Lett. 17 2007 2697
- (2007) Bioorg. Med. Chem. Lett. , vol.17 , pp. 2697
- Cox, C.¹ Breslin, M.² Whitman, D.³ Coleman, P.⁴ Garbaccio, R.⁵ Fraley, M.⁶ Zrada, M.⁷ Buser, C.⁸ Walsh, E.⁹ Mamilton, K.¹⁰ Lobell, R.¹¹ Tao, W.¹² Abrams, M.¹³ South, V.¹⁴ Huber, H.¹⁵ Kohl, N.¹⁶ Hartman, G.¹⁷

30
- 47749112809
- C.D. Cox, P.J. Coleman, M.J. Breslin, D.B. Whitman, R.M. Garbaccio, M.E. Fraley, C.A. Buser, E.S. Walsh, K. Hamilton, M.D. Schaber, R.B. Lobell, W. Tao, J.P. Davide, R.E. Diehl, M.T. Abrams, V.J. South, H.E. Huber, M. Torrent, T. Prueksaritanont, C. Li, D.E. Slaughter, E. Mahan, C. Fernandez-Metzler, Y. Yan, L.C. Kuo, N.E. Kohl, and G.D. Hartman J. Med. Chem. 51 2008 4239
- (2008) J. Med. Chem. , vol.51 , pp. 4239
- Cox, C.D.¹ Coleman, P.J.² Breslin, M.J.³ Whitman, D.B.⁴ Garbaccio, R.M.⁵ Fraley, M.E.⁶ Buser, C.A.⁷ Walsh, E.S.⁸ Hamilton, K.⁹ Schaber, M.D.¹⁰ Lobell, R.B.¹¹ Tao, W.¹² Davide, J.P.¹³ Diehl, R.E.¹⁴ Abrams, M.T.¹⁵ South, V.J.¹⁶ Huber, H.E.¹⁷ Torrent, M.¹⁸ Prueksaritanont, T.¹⁹ Li, C.²⁰ more..

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