$re = '~(?=.*/pdf/)(?!.*help)(.+)~';
$str = 'Shouldn\'t match: "/dealer/help/us/en/pdf/simple.pdf"
Should match: "/dealer/us/en/pdf/simple.pdf"';
preg_match($re, $str, $matches, PREG_OFFSET_CAPTURE, 0);
// Print the entire match result
var_dump($matches);
Please keep in mind that these code samples are automatically generated and are not guaranteed to work. If you find any syntax errors, feel free to submit a bug report. For a full regex reference for PHP, please visit: http://php.net/manual/en/ref.pcre.php