Substituted 2-carbonylamino-6-piperidinaminopyridines and substituted 1-carbonylamino-3-piperidinaminobenzenes as 5-HT1F agonists

US7291632B2 · kind B2 · utility

Assignee

• ELI LILLY AND COMPANY · US

Inventors

• Maria Jesus Blanco-Pillado · Indianapolis, US
• Michael Philip Cohen · Indianapolis, US
• Sandra Ann Filla · Ashland, US
• Kevin John Hudziak · Indianapolis, US
• Daniel Timothy Kohlman · Camby, US
• Dana Rae Benesh · Westfield, US
• Frantz Victor · Indianapolis, US
• Yao-Chang Xu · Indianapolis, US
• Bai-Ping Ying · Greenville, US
• DeAnna Piatt Zacherl · Noblesville, US
• Deyi Zhang · Carmel, US
• Brian Michael Mathes · Indianapolis, US

Key dates

• Filing date: Sep 3, 2004
• Grant date: Nov 6, 2007
• Expiry date: Sep 3, 2024

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D409/14
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

The present invention relates to compounds of formula I: (I) or a pharmaceutically acceptable acid addition salt thereof, where; X is C(R3c═ or N═; R1 is C2–C6 alkyl, substituted C2–C6 alkyl, C3–C7 cycloalkyl, substituted C3–C7 cycloalkyl, phenyl, substituted phenyl, heterocycle, or substituted heterocycle; R2 is hydrogen, C1–C3 n-alkyl, C3–C6 cycloalkyl-C1–C3 alkyl, or a group of formula II (II) provided that when R1 is C2–C6 alkyl or substituted C2–C6 alkyl, R2 is hydrogen or methyl; R3a, R3b, and, when X is C(R3c)═, R3c, are each independently hydrogen, fluoro, or methyl, provided that no more than one of R3a, R3b, and R3c may be other than hydrogen; R4 is hydrogen or C1–C3 alkyl; R5 is hydrogen, C1–C3 alkyl, or C3–C6 cycloalkylcarbonyl, provided that when R3a is other than hydrogen, R5 is hydrogen; R6 is hydrogen or C1–C6 alkyl; and n is an integer from 1 to 6 inclusively. The compounds of the present invention are useful for activating 5-HT1F receptors, inhibiting neuronal protein extravasation, and for the treatment or prevention of migraine in a mammal.