title: Potent antagonists of gonadotropin releasing hormone receptors derived from quinolone-6-carboxamides.
abstract: SAR studies which focused upon the C-6 position of a recently described series of quinolone gonadotropin releasing hormone antagonists are reported. Synthetic access to diverse quinolone-6-carboxamides was achieved via the palladium-catalyzed amino-carbonylation reactions of iodide 4 with various amines. Amides related to 9y were especially potent, functional antagonists of rat and human GnRH receptors.
authors.affiliation: Department of Medicinal Chemistry, Merck Research Laboratories, Rahway, NJ 07065-0900, USA.
authors.forename: T F
authors.initials: TF
authors.lastname: Walsh
authors.forename: R B
authors.initials: RB
authors.lastname: Toupence
authors.forename: J R
authors.initials: JR
authors.lastname: Young
authors.forename: S X
authors.initials: SX
authors.lastname: Huang
authors.forename: F
authors.initials: F
authors.lastname: Ujjainwalla
authors.forename: R J
authors.initials: RJ
authors.lastname: DeVita
authors.forename: M T
authors.initials: MT
authors.lastname: Goulet
authors.forename: M J
authors.initials: MJ
authors.lastname: Wyvratt
authors.forename: M H
authors.initials: MH
authors.lastname: Fisher
authors.forename: J L
authors.initials: JL
authors.lastname: Lo
authors.forename: N
authors.initials: N
authors.lastname: Ren
authors.forename: J B
authors.initials: JB
authors.lastname: Yudkovitz
authors.forename: Y T
authors.initials: YT
authors.lastname: Yang
authors.forename: K
authors.initials: K
authors.lastname: Cheng
authors.forename: R G
authors.initials: RG
authors.lastname: Smith
mesh_terms: D000577:Amides / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D016466:CHO Cells; D006224:Cricetinae; D006801:Humans; D007986:Luteinizing Hormone / Q000378:metabolism; D010716:Phosphatidylinositols / Q000378:metabolism; D015363:Quinolones / Q000138:chemical synthesis* / Q000494:pharmacology; D051381:Rats; D011966:Receptors, LHRH / Q000037:antagonists & inhibitors*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000577:Amides; D010716:Phosphatidylinositols; D015363:Quinolones; D011966:Receptors, LHRH; D007986:Luteinizing Hormone