Discovery of novel series of benzoic acid derivatives containing biphenyl ether moiety as potent and selective human β3-adrenergic receptor agonists:: Part IV

被引：8

作者：

Nakajima, Yutaka ^{[1
]}

Imanishi, Masashi ^{[1
]}

Itou, Shinji ^{[1
]}

Hamashima, Hitoshi ^{[1
]}

Tomishima, Yasuyo ^{[1
]}

Washizuka, Kenichi ^{[1
]}

Sakurai, Minoru ^{[1
]}

Matsui, Shigeo ^{[2
]}

Imamura, Emiko ^{[2
]}

Ueshima, Koji ^{[3
]}

Yamamoto, Takao ^{[2
]}

Yamamoto, Nobuhiro ^{[2
]}

Ishikawa, Hirofumi ^{[2
]}

Nakano, Keiko ^{[2
]}

Unami, Naoko ^{[2
]}

Hamada, Kaori ^{[2
]}

Hattori, Kouji ^{[1
]}

机构：

[1] Astellas Pharma Inc, Chem Res Labs, Tsukuba, Ibaraki 3058585, Japan

[2] Astellas Pharma Inc, Pharmacol Res Labs, Tsukuba, Ibaraki 3058585, Japan

[3] Astellas Pharma Inc, Appl Pharmacol Res Labs, Tsukuba, Ibaraki 3058585, Japan

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2008年 / 18卷 / 18期

关键词：

beta(3)-adrenergic receptor agonist; overactive bladder;

D O I：

10.1016/j.bmcl.2008.08.009

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Identification and SAR study of novel series of beta(3)-AR agonists with benzoic acid are described. Conversion of ether linkage position of phenoxybenzoic acid derivative 2b led to compound 7b with moderate b(3)-AR activity. Further modi. cation in right, center and left parts of compound 7b was investigated to improve the b(3)-AR potency and selectivity. Compounds 7g and 7k, with the bulky aliphatic-substituted group at 2-position of benzoic acid moiety, were identified as potent and selective b(3)-AR agonists. In addition, in vivo efficacy of compounds 7g and 7k was exhibited on dog OAB model. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：5037 / 5040

页数：4

共 40 条

[21] 4-Piperidino-benzoic acid derivatives:: Potent and selective human β3 agonists.
Hu, BH
Malamas, M
Sum, FW
Oliphant, A
Gunawan, I
Li, ZN
Wong, V
Niu, CS
Singanallore, T
Ellingboe, J
Largis, E
Han, S
Tillett, J
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 221 : U41 - U41
[22] Tryptamine-based human β3-adrenergic receptor agonists.: Part 2:: SAR of the methylene derivatives
Sawa, M
Tateishi, H
Mizuno, K
Harada, H
Oue, M
Tsujiuchi, H
Furutani, Y
Kato, S
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (24) : 5963 - 5966
[23] Discovery of 1,7-cyclized indoles as a new class of potent and highly selective human β3-adrenergic receptor agonists with high cell permeability
Mizuno, K
Sawa, M
Harada, H
Taoka, I
Yamashita, H
Oue, M
Tsujiuchi, H
Arai, Y
Suzuki, S
Furutani, Y
Kato, S
BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (03) : 855 - 868
[24] Discovery of Highly Potent and Selective Biphenylacylsulfonamide-Based β3-Adrenergic Receptor Agonists and Evaluation of Physical Properties as Potential Overactive Bladder Therapies: Part 5
Hattori, Kouji
Toda, Susumu
Imanishi, Masashi
Itou, Shinji
Nakajima, Yutaka
Washizuka, Kenichi
Araki, Takanobu
Hamashima, Hitoshi
Tomishima, Yasuyo
Sakurai, Minoru
Matsui, Shigeo
Imamura, Emiko
Ueshima, Koji
Yamamoto, Takao
Yamamoto, Nobuhiro
Ishikawa, Hirofumi
Nakano, Keiko
Unami, Naoko
Hamada, Kaori
Matsumura, Yasuhiro
Takamura, Fujiko
JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (09) : 3063 - 3072
[25] Discovery of highly potent and selective biphenylacylsulfonamide-based β3-adrenergic receptor agonists and molecular modeling based on the solved X-ray structure of the β2-adrenergic receptor: Part 6
Hattori, Kouji
Orita, Masaya
Toda, Susumu
Imanishi, Masashi
Itou, Shinji
Nakajima, Yutaka
Tanabe, Daisuke
Washizuka, Kenichi
Araki, Takanobu
Sakurai, Minoru
Matsui, Shigeo
Imamura, Emiko
Ueshima, Koji
Yamamoto, Takao
Yamamoto, Nobuhiro
Ishikawa, Hirofumi
Nakano, Keiko
Unami, Naoko
Hamada, Kaori
Matsumura, Yasuhiro
Takamura, Fujiko
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (16) : 4679 - 4683
[26] Tryptamine-based human β3-adrenergic receptor agonists.: Part 3:: Improved oral bioavailability via modification of the sulfonamide moiety
Sawa, M
Mizuno, K
Harada, H
Tateishi, H
Arai, Y
Suzuki, S
Oue, M
Tsujiuchi, H
Furutani, Y
Kato, S
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (04) : 1061 - 1064
[27] Metabolism of a thiazole benzenesulfonamide derivative, a potent and selective agonist of the human β3-adrenergic receptor, in rats:: Identification of a novel isethionic acid conjugate
Tang, W
Stearns, RA
Miller, RR
Ngui, JS
Mathvink, RJ
Weber, AE
Kwei, GY
Strauss, JR
Keohane, CA
Doss, GA
Chiu, SHL
Baillie, TA
DRUG METABOLISM AND DISPOSITION, 2002, 30 (07) : 778 - 787
[28] Discovery of a novel, potent and highly selective β3-adrenergic receptor agonist, SM-350300, for the treatment of overactive bladder syndrome
Hashizume, Miki
Hirota, Kotaro
Umezome, Takashi
Sawada, Nobuyuki
Ueno, Yoshihide
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 237
[29] Potent, selective human β3 adrenergic receptor agonists containing a substituted indoline-5-sulfonamide pharmacophore
Mathvink, RJ
Barritta, AM
Candelore, MR
Cascieri, MA
Deng, LP
Tota, L
Strader, CD
Wyvratt, MJ
Fisher, MH
Weber, AE
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (13) : 1869 - 1874
[30] Discovery of Novel Selective Human β3 Adrenergic Receptor Agonists as Potential Overactive Bladder (OAB) Therapies
Imanishi, Masashi
Hattori, Kouji
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2011, 69 (12) : 1402 - 1410

← 1 2 3 4 →