Power lost = current x voltage
You can break this down further to figure this out simply as possible I could go into the dy/dx differentiation but I wont.
Ok first for a set power line the resistance is a fixed amount. So it won't change but we can substitute it for some values in the first equation.
First substitute it for current:
Current = voltage / resistance
So:
Power lost = voltage2 / resistance
Next substitute it for voltage:
Voltage = current x resistance
So:
Power lost = current2 x resistance
You see the subtle difference there? In the first one the resistance is deviding the square of the voltage so in a large power grid with high resistance a high voltage devided by a high resistance is ok.
In the second one the square of the current is multiplied by the resistance so in a high current with a large grid with large resistance this is a worse situation.
Couple this to the need to carry a given amount of power along the grid you get a situation where having a high voltage low current reduces losses but a high current low voltage increases the losses.