(?:^|\s)((?:[^h ]|h(?!elp))+\/pdf\/\S*)(?:$|\s)
First thing is match either a space or the start of a line
(?:^|\s)
Then we match anything that is not a h OR any h that does not have elp behind it, one or more times +, until we find a /pdf/, then match non-space characters \S any number of times *.
((?:[^h ]|h(?!elp))+\/pdf\/\S*)
If we want to detect help after the /pdf/, we can duplicate matching from the start.
((?:[^h ]|h(?!elp))+\/pdf\/(?:[^h ]|h(?!elp))+)
Finally, we match a $)
(?:$|\s)
The full match will include leading/trailing spaces, and should be stripped. If you use capture group 1, you don't need to strip the ends.
Example on regex101