Debugging and Deep sleep do not match.
The inverter you use does not work in Deep Sleep. Best would be to use the interrupt feature of the port for one pin which will wakeup the device.
Some ref material -
http://www.cypress.com/documentation/application-notes/an86233-psoc-4-low-power-modes-and-power-reduction-techniques AN86233 - PSoC® 4 Low-Power Modes and Power Reduction Techniques
http://www.cypress.com/documentation/application-notes/an90114-psoc-4000-family-low-power-system-design-techniques AN90114 - PSoC® 4000 Family Low-Power System Design Techniques
http://www.cypress.com/documentation/application-notes/an92584-designing-low-power-and-estimating-battery-life-ble AN92584 - Designing for Low Power and Estimating Battery Life for BLE Applications
Thanks! issue is resolved by adding falling edge interrupt to port, and connecting to ISR using 'derived' setting. I will keep adding low power wingdings, and repost as challenges develop.