There have been a few, Its time consuming and expensive. The NYRPA has a list of cases they have been involved with, its quite a few. Remember every one not won is a president for the other side.

This one is at SCOTUS now.
https://www.subscriptlaw.com/blog/ny-rifle-and-pistol-v-nyc


This one went to the US district court but lost
https://www.nysrpa.org/files/SAFE/Halbrook-SAFE-Review.pdf

The collection of taxes which are not absolutely required, which do not beyond reasonable doubt contribute to public welfare, is only a species of legalized larceny. Under this Republic the rewards of industry belong to those who earn them. Coolidge