Pyrrolinone derivatives as a new class of P2X3 receptor antagonists Part 2: Discovery of orally bioavailable compounds.


Journal

Bioorganic & medicinal chemistry letters
ISSN: 1464-3405
Titre abrégé: Bioorg Med Chem Lett
Pays: England
ID NLM: 9107377

Informations de publication

Date de publication:
01 03 2019
Historique:
received: 21 10 2018
revised: 28 01 2019
accepted: 30 01 2019
pubmed: 8 2 2019
medline: 15 2 2020
entrez: 8 2 2019
Statut: ppublish

Résumé

Some P2X3 receptor antagonists have been developed as new therapeutic drugs for pain. We discovered a novel chemotype of P2X3 receptor antagonists with a pyrrolinone skeleton. Because of SAR studies to improve bioavailability of lead compound 2, compound (R)-24 was identified, which showed an analgesic effect against neuropathic pain by oral administration. We constructed a human P2X3 homology model as a template for the zebrafish P2X4 receptor, which agreed with SAR studies of pyrrolinone derivatives.

Identifiants

pubmed: 30728111
pii: S0960-894X(19)30060-5
doi: 10.1016/j.bmcl.2019.01.039
pii:
doi:

Substances chimiques

Purinergic P2X Receptor Antagonists 0
Pyrroles 0
Receptors, Purinergic P2X3 0

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

688-693

Informations de copyright

Copyright © 2019 Elsevier Ltd. All rights reserved.

Auteurs

Hiroyuki Tobinaga (H)

Medicinal Chemistry Research Laboratory, Shionogi & Co., Ltd., 1-1 Futaba-cho 3-chome, Toyonaka, Osaka 561-0825, Japan. Electronic address: hiroyuki.tobinaga@shionogi.co.jp.

Takayuki Kameyama (T)

Office for Children's Bright Future, Shionogi & Co., Ltd., 2F, Nissay Yodoyabashi East, 3-13, Imabashi 3-chome, Chuo-ku, Osaka 541-0042, Japan.

Kentarou Asahi (K)

Medicinal Chemistry Research Laboratory, Shionogi & Co., Ltd., 1-1 Futaba-cho 3-chome, Toyonaka, Osaka 561-0825, Japan.

Tohru Horiguchi (T)

Medicinal Chemistry Research Laboratory, Shionogi & Co., Ltd., 1-1 Futaba-cho 3-chome, Toyonaka, Osaka 561-0825, Japan.

Miho Oohara (M)

Medicinal Chemistry Research Laboratory, Shionogi & Co., Ltd., 1-1 Futaba-cho 3-chome, Toyonaka, Osaka 561-0825, Japan.

Yukio Tada (Y)

Medicinal Chemistry Research Laboratory, Shionogi & Co., Ltd., 1-1 Futaba-cho 3-chome, Toyonaka, Osaka 561-0825, Japan.

Kouki Fuchino (K)

Medicinal Chemistry Research Laboratory, Shionogi & Co., Ltd., 1-1 Futaba-cho 3-chome, Toyonaka, Osaka 561-0825, Japan.

Sae Jikihara (S)

Digital Intelligence Department, Shionogi & Co., Ltd., 2F, Nissay Yodoyabashi East, 3-13, Imabashi 3-chome, Chuo-ku, Osaka 541-0042, Japan.

Takeshi Endoh (T)

Research Management & Planning Office, Shionogi & Co., Ltd., 1-1 Futaba-cho, 3-chome, Toyonaka, Osaka 561-0825, Japan.

Naoko Kurihara (N)

Drug Discovery & Disease Research Laboratory, Shionogi & Co., Ltd., 1-1 Futaba-cho, 3-chome, Toyonaka, Osaka 561-0825, Japan.

Yasuhiko Kanda (Y)

Medicinal Chemistry Research Laboratory, Shionogi & Co., Ltd., 1-1 Futaba-cho 3-chome, Toyonaka, Osaka 561-0825, Japan.

Masayoshi Ogawa (M)

Medicinal Chemistry Research Laboratory, Shionogi & Co., Ltd., 1-1 Futaba-cho 3-chome, Toyonaka, Osaka 561-0825, Japan.

Naomi Tamura (N)

Research Laboratory for Development, Shionogi & Co., Ltd., 1-1 Futaba-cho, 3-chome, Toyonaka, Osaka 561-0825, Japan.

Shigenori Yagi (S)

API R&D Center, Shionogi & Co., Ltd., 1-3, Kuise Terajima 2-chome, Amagasaki, Hyogo 660-0813, Japan.

Emiko Taniguchi (E)

Drug Discovery & Disease Research Laboratory, Shionogi & Co., Ltd., 1-1 Futaba-cho, 3-chome, Toyonaka, Osaka 561-0825, Japan.

Yukio Takahara (Y)

Drug Discovery & Disease Research Laboratory, Shionogi & Co., Ltd., 1-1 Futaba-cho, 3-chome, Toyonaka, Osaka 561-0825, Japan.

Shinji Shimada (S)

Shionogi Techno Advance Research Co., Ltd., 1-1 Futaba-cho, 3-chome, Toyonaka, Osaka 561-0825, Japan.

Chie Takeyama (C)

Shionogi Techno Advance Research Co., Ltd., 1-1 Futaba-cho, 3-chome, Toyonaka, Osaka 561-0825, Japan.

Shoichi Yamamoto (S)

Shionogi Marketing Solutions Co., Ltd., 8F, Nissay Yodoyabashi East, 3-13, Imabashi 3-chome, Chuo-ku, Osaka 541-0042, Japan.

Shunji Shinohara (S)

Shionogi Techno Advance Research Co., Ltd., 1-1 Futaba-cho, 3-chome, Toyonaka, Osaka 561-0825, Japan.

Hiroyuki Kai (H)

Medicinal Chemistry Research Laboratory, Shionogi & Co., Ltd., 1-1 Futaba-cho 3-chome, Toyonaka, Osaka 561-0825, Japan. Electronic address: hiroyuki.kai@shionogi.co.jp.

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Classifications MeSH