I don't understand which logic leads from 'Oct 10 05:59:59' to 'Oct 10 05:5[0-2]:'

but yes, you can put a datetime-string into a variable, dynamically manipulate this variable and use it as a pattern within any regex.

my $dt =  'Oct 10 05:59:59';
$dt    =~ s/9:59$/[0-2]:/;
$file  =~ m/$dt/;
[download]

HTH!