Atogepant

• CAT Number: I003177
• CAS Number: 1374248-81-3
• Molecular Formula: C29H23F6N5O3
• Molecular Weight: 603.525
• Purity: ≥95%
• Synonyms: MK-8031; MK 8031; MK8031. Atogepant.;(3/’S)-N-[(3S,5S,6R)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2/’-oxo-1/’,2/’,5,7-tetrahydrospiro[cyclopenta[b]pyridine-6,3/’-pyrrolo[2,3-b]pyridine]-3-carboxamide
• Solubility: Soluble in DMSO
• Storage: 0 - 4 °C for short term or -20 °C for long term
• IUPAC Name: (3S)-N-[(3S,5S,6R)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1H-pyrrolo[2,3-b]pyridine-3,6/'-5,7-dihydrocyclopenta[b]pyridine]-3/'-carboxamide
• InChI: InChI=1S/C29H23F6N5O3/c1-13-16(22-18(30)4-5-19(31)23(22)32)8-20(26(42)40(13)12-29(33,34)35)38-25(41)15-7-14-9-28(10-21(14)37-11-15)17-3-2-6-36-24(17)39-27(28)43/h2-7,11,13,16,20H,8-10,12H2,1H3,(H,38,41)(H,36,39,43)/t13-,16-,20+,28+/m1/s1
• InChIKey: QIVUCLWGARAQIO-OLIXTKCUSA-N
• SMILES: O=C1[C@@]2(C=3C(N1)=NC=CC3)CC=4C(C2)=NC=C(C(N[C@H]5C[C@H]([C@@H](C)N(CC(F)(F)F)C5=O)C6=C(F)C(F)=CC=C6F)=O)C4

Atogepant(CAT: I003177) is a CGRP receptor antagonist that is currently being developed as a potential treatment for migraines. Migraine headaches are believed to be triggered by the release of CGRP, a neuropeptide that plays a crucial role in their pathogenesis. Atogepant works by inhibiting the activity of the CGRP receptor, thereby reducing the frequency and severity of migraine headaches. It has been shown to be effective in several clinical trials, and further studies are ongoing. While Atogepant is generally well-tolerated, common side effects may include nausea, fatigue, and constipation. It is important to note that Atogepant is intended for research purposes only and should not be used for any other purposes.

Reference

1. Preparation of piperidinonylcarboxamideazaindane derivatives for use as CGRP receptor antagonists

By: Bell, Ian M.; Fraley, Mark E.; Gallicchio, Steven N.; Ginnetti, Anthony; Mitchell, Helen J.; Paone, Daniel V.; Staas, Donnette D.; Wang, Cheng; Zartman, C. Blair; Stevenson, Heather E.
Assignee: Merck Sharp & Dohme Corp., USA
Patent Information: May 18, 2012, WO 2012064910, A1
Application: Nov 10, 2011, WO 2011-US60081
Priority: Nov 12, 2010, US 2010-61413077, Dec 20, 2010, US 2010-61425034, Nov 10, 2011, WO 2011-US60081, Nov 10, 2011, EP 2011-787987, Nov 10, 2011, US 2011-13293177, Sep 12, 2014, US 2014-14485259
Source: PCT Int. Appl., 93pp., Patent, 2012, CODEN: PIXXD2

Language: English

Abstract
Title compds. I [X = CH, CF, CCN, or N; R1 = (un)substituted alkyl, cyclopropylmethyl, cyclobutylmethyl, or [1-(trifluoromethyl)cyclopropyl]methyl; R2 = H or Me; R3, R4, and R7 independently = H, F, Cl, etc.; R5 and R6 independently = H or F; with provisions], and their pharmaceutically acceptable salts, are prepd. and disclosed as CGRP receptor antagonists. Thus, e.g., II was prepd. by a multistep procedure (prepn. given). Select I were evaluated in recombinant receptor functional assays, e.g., II demonstrated a Ki value of 0.067 nM.