for the drill chuck I agree that it is MT. Remove the pull stud, it unscrews, and use a drift to drive the chuck out. If that doesn't work then remove the chuck from the taper at the chuck with wedges.
For the boring bar I would think it would unscrew. If there is a number on the cat 50 you could look it up.
It might be t his one, https://www.lyndexnikken.com/BT50-7-8-20-Boring-Head-Holder-1120p726.htm