Try this:

^\d{5}\s{6}[\s\*]   # Your original pattern
(?:                 # Repeat 0 or more times:
  [^.:;()]*|        # Unconstrained characters
  (?<!\s)[.:;](?=\s)|    # Punctuation after non-space, followed by space
  \((?!\s)|         # Opening parentheses not followed by space
  (?<!\s)\)         # Closing parentheses not preceeded by space
\.$                 # Period, then end of string

In the last part of the pattern, the characters with special requirements are .:;(), so use a negative character set to match anything but those characters: [^.:;()]* Then alternate with:

if there is any period, colon or semicolon before the final period, the character must not be preceded by a white space, but it must be followed by a white space.

Fulfilled by (?<!\s)[.:;](?=\s) – match one of those characters only if not preceded by a space, and if followed by a space.

opening parentheses cannot be followed by a white space.

Fulfilled by \((?!\s)

closing parentheses cannot be preceded by a white space.

Fulfilled by (?<!\s)\)

Then just alternate between those 4 possibilities at the end of the pattern.

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