LOUISVILLE, Ky. — A man who killed three of his classmates at a Kentucky high school in 1997 has lost his bid to withdraw a guilty plea after a federal appeals court concluded that he could have acted sooner to seek a new trial.

The U.S. 6th Circuit Court of Appeals in Cincinnati ruled Thursday that Michael Carneal, 29, was competent as early as 2004 and could have challenged the plea then.

Carneal shot at a school prayer meeting in Paducah, killing Jessica James, 17, Kayce Steger, 15, and Nicole Hadley, 14. Five others were wounded.