SCOPUS 정보 검색 플랫폼

Volumn 19, Issue 13, 2011, Pages 4028-4042

Discovery of 4-[4-({(3R)-1-butyl-3-[(R)-cyclohexyl(hydroxy)methyl]-2,5- dioxo-1,4,9-triazaspiro[5.5]undec-9-yl}methyl)phenoxy]benzoic acid hydrochloride: A highly potent orally available CCR5 selective antagonist

(13) Nishizawa, Rena a Nishiyama, Toshihiko a Hisaichi, Katsuya a Minamoto, Chiaki a Murota, Masayuki a Takaoka, Yoshikazu a Nakai, Hisao a Tada, Hideaki a Sagawa, Kenji a Shibayama, Shiro a Fukushima, Daikichi a Maeda, Kenji b,c Mitsuya, Hiroaki b,c

a ONO PHARMACEUTICAL CO (Japan)

b KUMAMOTO UNIV SCHOOL OF MEDICINE (Japan)

c NATIONAL CANCER INSTITUTE (United States)

Author keywords

Anti HIV 1; CCR5; Chemokine

Indexed keywords

4 [(4 BROMOPHENYL)(ETHOXYIMINO)METHYL] 1' [(2,4 DIMETHYL 3 PYRIDINYL)CARBONYL] 4' METHYL 1,4' BIPIPERIDINE; 4 [4 [[1 BUTYL 3 [CYCLOHEXYL(HYDROXY)METHYL] 2,5 DIOXO 1,4,9 TRIAZASPIRO[5.5]UNDEC 9 YL]METHYL]PHENOXY]BENZOIC ACID HYDROCHLORIDE; BENZOIC ACID DERIVATIVE; CHEMOKINE RECEPTOR CCR5; CHEMOKINE RECEPTOR CCR5 ANTAGONIST; CHEMOKINE RECEPTOR CXCR4; MACROPHAGE INFLAMMATORY PROTEIN 1ALPHA; N [4 [[[6,7 DIHYDRO 2 (4 METHYLPHENYL) 5H BENZOCYCLOHEPTEN 8 YL]CARBONYL]AMINO]BENZYL] N,N DIMETHYL 2H TETRAHYDROPYRAN 4 AMINIUM CHLORIDE; NELFINAVIR; PIPERAZINEDIONE; STROMAL CELL DERIVED FACTOR 1; UNCLASSIFIED DRUG; ZIDOVUDINE;

ANIMAL EXPERIMENT; ANTIVIRAL ACTIVITY; AREA UNDER THE CURVE; ARTICLE; CONTROLLED STUDY; DOG; DRUG ABSORPTION; DRUG CLEARANCE; DRUG DISTRIBUTION; DRUG EXCRETION; DRUG HALF LIFE; DRUG METABOLISM; DRUG POTENCY; DRUG SELECTIVITY; DRUG STRUCTURE; HAPLORHINI; HUMAN IMMUNODEFICIENCY VIRUS 1; HYBRIDIZATION; HYDROXYLATION; MAXIMUM PLASMA CONCENTRATION; NONHUMAN; RAT; RECEPTOR BINDING; STRUCTURE ACTIVITY RELATION;

ADMINISTRATION, ORAL; ANIMALS; ANTI-HIV AGENTS; BENZOIC ACIDS; DIKETOPIPERAZINES; DOGS; DRUG EVALUATION, PRECLINICAL; GUINEA PIGS; HAPLORHINI; HUMANS; RABBITS; RATS; RECEPTORS, CCR5; STRUCTURE-ACTIVITY RELATIONSHIP;

HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 79959496241 PISSN: 09680896 EISSN: 14643391 Source Type: Journal
DOI: 10.1016/j.bmc.2011.05.022 Document Type: Article

Times cited : (9)

References (32)

1
- 65549140728
- D.R. Kuritzkes Curr. Opin. HIV/AIDS 4 2009 82
- (2009) Curr. Opin. HIV/AIDS , vol.4 , pp. 82
- Kuritzkes, D.R.¹

2
- 0011227011
- Second ed. Williams & Wilkins
- H. Mitsuya, and J. Erickson Textbook of AIDS Medicine Second ed. 2001 Williams & Wilkins 751 780
- (2001) Textbook of AIDS Medicine , pp. 751-780
- Mitsuya, H.¹ Erickson, J.²

3
- 72249085764
- Overview of antiretroviral agents
- Hoffmann, C., Rockstroh, J. K., Kamps, B. S., Eds.; Flying Publisher (FlyingPublisher.com): Paris
- Hoffmann, C.; Mulcahy, F. Overview of Antiretroviral Agents. In HIV Medicine 2006; Hoffmann, C., Rockstroh, J. K., Kamps, B. S., Eds.; Flying Publisher (FlyingPublisher.com): Paris, 2006; pp 94.
- (2006) HIV Medicine 2006 , pp. 94
- Hoffmann, C.¹ Mulcahy, F.²

4
- 77249134151
- Y. Mehellou, and E.D. Clercq J. Med. Chem. 53 2010 521
- (2010) J. Med. Chem. , vol.53 , pp. 521
- Mehellou, Y.¹ Clercq, E.D.²

5
- 34347378496
- J.A. Este, and A. Telenti Lancet 370 2007 81
- (2007) Lancet , vol.370 , pp. 81
- Este, J.A.¹ Telenti, A.²

6
- 33645116573
- V. Briz, E. Poveda, and V. Soriano J. Antimicrob. Chemother. 57 2006 619
- (2006) J. Antimicrob. Chemother. , vol.57 , pp. 619
- Briz, V.¹ Poveda, E.² Soriano, V.³

7
- 0030002637
- Y. Feng, C.C. Broder, P.E. Kennedy, and E.A. Berger Science 272 1996 872
- (1996) Science , vol.272 , pp. 872
- Feng, Y.¹ Broder, C.C.² Kennedy, P.E.³ Berger, E.A.⁴

8
- 15844419153
- H.K. Deng, R. Liu, W. Ellmeier, S. Choe, D. Unutmaz, M. Burkhart, P.D. Marzio, S. Marmon, R.E. Sutton, C.M. Hill, C.B. Davis, S.C. Peiper, T.J. Schall, D.R. Littman, and N.R. Landau Nature 381 1996 661
- (1996) Nature , vol.381 , pp. 661
- Deng, H.K.¹ Liu, R.² Ellmeier, W.³ Choe, S.⁴ Unutmaz, D.⁵ Burkhart, M.⁶ Marzio, P.D.⁷ Marmon, S.⁸ Sutton, R.E.⁹ Hill, C.M.¹⁰ Davis, C.B.¹¹ Peiper, S.C.¹² Schall, T.J.¹³ Littman, D.R.¹⁴ Landau, N.R.¹⁵

9
- 15844389650
- T. Dragic, V. Litwin, G.P. Allaway, S.R. Martin, Y. Huang, K.A. Nagashima, C. Cayanan, P.J. Maddon, R.A. Koup, J.P. Moore, and W.A. Paxton Nature 381 1996 667
- (1996) Nature , vol.381 , pp. 667
- Dragic, T.¹ Litwin, V.² Allaway, G.P.³ Martin, S.R.⁴ Huang, Y.⁵ Nagashima, K.A.⁶ Cayanan, C.⁷ Maddon, P.J.⁸ Koup, R.A.⁹ Moore, J.P.¹⁰ Paxton, W.A.¹¹

10
- 0030018156
- G. Alkhatib, C. Combadiere, C.C. Broder, Y. Feng, P.E. Kennedy, P.M. Murphy, and E.A. Berger Science 272 1996 1955
- (1996) Science , vol.272 , pp. 1955
- Alkhatib, G.¹ Combadiere, C.² Broder, C.C.³ Feng, Y.⁴ Kennedy, P.E.⁵ Murphy, P.M.⁶ Berger, E.A.⁷

11
- 0033012398
- E.A. Berger, P.M. Murphy, and J.M. Farber Annu. Rev. Immunol. 17 1999 657
- (1999) Annu. Rev. Immunol. , vol.17 , pp. 657
- Berger, E.A.¹ Murphy, P.M.² Farber, J.M.³

12
- 59449093055
- D.J. Caldwell, and J.D. Evans Expert Opin. Pharmacother. 9 2008 3231
- (2008) Expert Opin. Pharmacother. , vol.9 , pp. 3231
- Caldwell, D.J.¹ Evans, J.D.²

13
- 16044367526
- Y. Huang, W.A. Paxton1, S.M. Wolinsky, A.U. Neumann, L. Zhang, T. He, S. Kang, D. Ceradini1, Z. Jin, K. Yazdanbakhsh, K. Kunstman, D. Erickson, E. Dragon, N.R. Landau, J. Phair, D.D. Ho, and R.A. Koup Nat. Med. 2 1996 1240
- (1996) Nat. Med. , vol.2 , pp. 1240
- Huang, Y.¹ Paxton, W.A.² Wolinsky, S.M.³ Neumann, A.U.⁴ Zhang, L.⁵ He, T.⁶ Kang, S.⁷ Ceradini, D.⁸ Jin, Z.⁹ Yazdanbakhsh, K.¹⁰ Kunstman, K.¹¹ Erickson, D.¹² Dragon, E.¹³ Landau, N.R.¹⁴ Phair, J.¹⁵ Ho, D.D.¹⁶ Koup, R.A.¹⁷

14
- 35948935297
- W.M. Kazmierski, K.S. Gudmundsson, and S.C. Piscitelli Annu. Rep. Med. Chem. 42 2007 301
- (2007) Annu. Rep. Med. Chem. , vol.42 , pp. 301
- Kazmierski, W.M.¹ Gudmundsson, K.S.² Piscitelli, S.C.³

15
- 79959514214
- R.C. Lemoine, and J. Wanner Curr. Top. Med. Chem. 10 2010 99
- (2010) Curr. Top. Med. Chem. , vol.10 , pp. 99
- Lemoine, R.C.¹ Wanner, J.²

16
- 27644510382
- P. Dorr, M. Westby, S. Dobbs, P. Griffin, B. Irvine, M. Macartney, J. Mori, G. Rickett, C. Smith-Burchnell, C. Napier, R. Webster, D. Armour, D. Price, B. Stammen, A. Wood, and M. Perros Antimicrob. Agents Chemother. 49 2005 4721
- (2005) Antimicrob. Agents Chemother. , vol.49 , pp. 4721
- Dorr, P.¹ Westby, M.² Dobbs, S.³ Griffin, P.⁴ Irvine, B.⁵ MacArtney, M.⁶ Mori, J.⁷ Rickett, G.⁸ Smith-Burchnell, C.⁹ Napier, C.¹⁰ Webster, R.¹¹ Armour, D.¹² Price, D.¹³ Stammen, B.¹⁴ Wood, A.¹⁵ Perros, M.¹⁶

17
- 27744548649
- A. Wood, and D. Armour Prog. Med. Chem. 43 2005 239
- (2005) Prog. Med. Chem. , vol.43 , pp. 239
- Wood, A.¹ Armour, D.²

18
- 0035860744
- K. Maeda, K. Yoshimura, S. Shibayama, H. Habashita, H. Tada, K. Sagawa, T. Miyakawa, M. Aoki, D. Fukushima, and H. Mitsuya J. Biol. Chem. 276 2001 35194
- (2001) J. Biol. Chem. , vol.276 , pp. 35194
- Maeda, K.¹ Yoshimura, K.² Shibayama, S.³ Habashita, H.⁴ Tada, H.⁵ Sagawa, K.⁶ Miyakawa, T.⁷ Aoki, M.⁸ Fukushima, D.⁹ Mitsuya, H.¹⁰

19
- 33745807624
- H. Habashita, M. Kokubo, S. Hamano, N. Hamanaka, M. Toda, S. Shibayama, H. Tada, K. Sagawa, D. Fukushima, K. Maeda, and H. Mitsuya J. Med. Chem. 49 2006 4140
- (2006) J. Med. Chem. , vol.49 , pp. 4140
- Habashita, H.¹ Kokubo, M.² Hamano, S.³ Hamanaka, N.⁴ Toda, M.⁵ Shibayama, S.⁶ Tada, H.⁷ Sagawa, K.⁸ Fukushima, D.⁹ Maeda, K.¹⁰ Mitsuya, H.¹¹

20
- 33846354589
- R. Nishizawa, T. Nishiyama, K. Hisaichi, N. Matsunaga, C. Minamoto, H. Habashita, Y. Takaoka, M. Toda, S. Shibayama, H. Tada, K. Sagawa, D. Fukushima, K. Maeda, and H. Mitsuya Bioorg. Med. Chem. Lett. 17 2007 727
- (2007) Bioorg. Med. Chem. Lett. , vol.17 , pp. 727
- Nishizawa, R.¹ Nishiyama, T.² Hisaichi, K.³ Matsunaga, N.⁴ Minamoto, C.⁵ Habashita, H.⁶ Takaoka, Y.⁷ Toda, M.⁸ Shibayama, S.⁹ Tada, H.¹⁰ Sagawa, K.¹¹ Fukushima, D.¹² Maeda, K.¹³ Mitsuya, H.¹⁴

21
- 72549086139
- R. Nishizawa, T. Nishiyama, K. Hisaichi, K. Hirai, H. Habashita, Y. Takaoka, H. Tada, K. Sagawa, S. Shibayama, K. Maeda, H. Mitsuya, H. Nakai, D. Fukushima, and M. Toda Bioorg. Med. Chem. Lett. 20 2010 763
- (2010) Bioorg. Med. Chem. Lett. , vol.20 , pp. 763
- Nishizawa, R.¹ Nishiyama, T.² Hisaichi, K.³ Hirai, K.⁴ Habashita, H.⁵ Takaoka, Y.⁶ Tada, H.⁷ Sagawa, K.⁸ Shibayama, S.⁹ Maeda, K.¹⁰ Mitsuya, H.¹¹ Nakai, H.¹² Fukushima, D.¹³ Toda, M.¹⁴

22
- 77955329654
- R. Nishizawa, T. Nishiyama, K. Hisaichi, K. Hirai, H. Habashita, Y. Takaoka, H. Tada, K. Sagawa, S. Shibayama, K. Maeda, H. Mitsuya, H. Nakai, D. Fukushima, and M. Toda Bioorg. Med. Chem. 18 2010 5208
- (2010) Bioorg. Med. Chem. , vol.18 , pp. 5208
- Nishizawa, R.¹ Nishiyama, T.² Hisaichi, K.³ Hirai, K.⁴ Habashita, H.⁵ Takaoka, Y.⁶ Tada, H.⁷ Sagawa, K.⁸ Shibayama, S.⁹ Maeda, K.¹⁰ Mitsuya, H.¹¹ Nakai, H.¹² Fukushima, D.¹³ Toda, M.¹⁴

23
- 68049140888
- A. Ugi Domling, and I. Ugi Angew. Chem., Int. Ed. 39 2000 3168
- (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 3168
- Ugi Domling, A.¹ Ugi, I.²

24
- 0025252275
- C.G. Caldwell, and S.S. Bondy Synthesis 1990 34
- (1990) Synthesis , pp. 34
- Caldwell, C.G.¹ Bondy, S.S.²

25
- 18844410382
- Y. Gao, R.M. Hanson, J.M. Klunder, S.Y. Ko, H. Masamune, and K.B. Sharpless J. Am. Chem. Soc. 109 1987 5765
- (1987) J. Am. Chem. Soc. , vol.109 , pp. 5765
- Gao, Y.¹ Hanson, R.M.² Klunder, J.M.³ Ko, S.Y.⁴ Masamune, H.⁵ Sharpless, K.B.⁶

26
- 0029995939
- T. Nagamitsu, T. Sunazuka, H. Tanaka, S. Omura, P.A. Sprengeler, and A.B. Smith III J. Am. Chem. Soc. 118 1996 3584
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 3584
- Nagamitsu, T.¹ Sunazuka, T.² Tanaka, H.³ Omura, S.⁴ Sprengeler, P.A.⁵ Smith III, A.B.⁶

27
- 0028364176
- A. Solladie-Cavallo, and J.L. Koessler J. Org. Chem. 59 1994 3240
- (1994) J. Org. Chem. , vol.59 , pp. 3240
- Solladie-Cavallo, A.¹ Koessler, J.L.²

28
- 2142740431
- S. Jenkinson, D.C. McCoy, S.A. Kerner, R.G. Ferris, W.K. Lawrence, W.C. Clay, J.P. Condreay, and C. Smith J. Biomol. Screening 8 2003 463
- (2003) J. Biomol. Screening , vol.8 , pp. 463
- Jenkinson, S.¹ McCoy, D.C.² Kerner, S.A.³ Ferris, R.G.⁴ Lawrence, W.K.⁵ Clay, W.C.⁶ Condreay, J.P.⁷ Smith, C.⁸

29
- 3543144738
- K. Maeda, H. Nakata, Y. Koh, T. Miyakawa, H. Ogata, Y. Takaoka, S. Shibayama, K. Sagawa, D. Fukushima, J. Moravek, Y. Koyanagi, and H. Mitsuya J. Virol. 78 2004 8654
- (2004) J. Virol. , vol.78 , pp. 8654
- Maeda, K.¹ Nakata, H.² Koh, Y.³ Miyakawa, T.⁴ Ogata, H.⁵ Takaoka, Y.⁶ Shibayama, S.⁷ Sagawa, K.⁸ Fukushima, D.⁹ Moravek, J.¹⁰ Koyanagi, Y.¹¹ Mitsuya, H.¹²

30
- 79851510993
- R. Nishizawa, T. Nishiyama, K. Hisaichi, K. Hirai, H. Habashita, Y. Takaoka, H. Tada, K. Sagawa, S. Shibayama, K. Maeda, H. Mitsuya, H. Nakai, D. Fukushima, and M. Toda Bioorg. Med. Chem. Lett. 21 2011 1141
- (2011) Bioorg. Med. Chem. Lett. , vol.21 , pp. 1141
- Nishizawa, R.¹ Nishiyama, T.² Hisaichi, K.³ Hirai, K.⁴ Habashita, H.⁵ Takaoka, Y.⁶ Tada, H.⁷ Sagawa, K.⁸ Shibayama, S.⁹ Maeda, K.¹⁰ Mitsuya, H.¹¹ Nakai, H.¹² Fukushima, D.¹³ Toda, M.¹⁴

31
- 13044256383
- M.T. Baba, O. Nishimura, N. Kanzaki, M. Okamoto, H. Sawada, Y. Iizawa, M. Shiraishi, Y. Aramaki, K. Okonogi, Y. Ogawa, K. Meguro, and M. Fujino PNAS 96 1999 5698
- (1999) PNAS , vol.96 , pp. 5698
- Baba, M.T.¹ Nishimura, O.² Kanzaki, N.³ Okamoto, M.⁴ Sawada, H.⁵ Iizawa, Y.⁶ Shiraishi, M.⁷ Aramaki, Y.⁸ Okonogi, K.⁹ Ogawa, Y.¹⁰ Meguro, K.¹¹ Fujino, M.¹²

32
- 0035940445
- J.M. Strizki, S. Xu, N.E. Wagner, L. Wojcik, J. Liu, Y. Hou, M. Endres, A. Palani, S. Shapiro, J.W. Clader, W.J. Greenlee, J.R. Tagat, S. McCombie, K. Cox, A.B. Fawzi, C.-Chu. Chou, C. Pugliese-Sivo, L. Davies, M.E. Moreno, D.D. Ho, A. Trkola, C.A. Stoddart, J.P. Moore, G.R. Reyes, and B.M. Baroudy PNAS 98 2001 12718
- (2001) PNAS , vol.98 , pp. 12718
- Strizki, J.M.¹ Xu, S.² Wagner, N.E.³ Wojcik, L.⁴ Liu, J.⁵ Hou, Y.⁶ Endres, M.⁷ Palani, A.⁸ Shapiro, S.⁹ Clader, J.W.¹⁰ Greenlee, W.J.¹¹ Tagat, J.R.¹² McCombie, S.¹³ Cox, K.¹⁴ Fawzi, A.B.¹⁵ Chou, C.-Chu.¹⁶ Pugliese-Sivo, C.¹⁷ Davies, L.¹⁸ Moreno, M.E.¹⁹ Ho, D.D.²⁰ more..

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.