re = /(?:(?s:START.*?END)|\/\/.*|\.\s*\w+\b)(*SKIP)(*F)|old/
str = '__DATA__
xx START xx old xx END xx --> ignore
xx old xx --> REPLACE !
START xx old --> ignore
xx old xx END --> ignore
xx old xx --> REPLACE !
// xx old --> ignore
xx // xx old --> ignore
xx . old old xx --> ignore first one, replace second one
.
old --> ignore
(old) xx --> REPLACE !
xx old xx --> REPLACE !'
subst = 'new'
result = str.gsub(re, subst)
# Print the result of the substitution
puts result
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 Ruby, please visit: http://ruby-doc.org/core-2.2.0/Regexp.html