Hi
The Ability to stop the timer in Debug mode mark with circle in your screenshot refers to: If CR[FRZ] = 1, STM stops the timer. Otherwise, when the timer is enabled (CR[TEN] = 1), the timer counts up continuously.
If the timer is stopped in debug mode, then its interrupt will not happen. Is this what you want to achieve?
68.3.3 Behavior in different chip modes.jpg
Best Regards,
Robin