With my son when he is fighting sleep i put him in a quiet room and leave him be. He will cry for up to 15 minutes but eventually he will fall asleep even if it is for only 15-30 minutes it improves his demeanor.
As far as the waking up after being put to bed, my son did that for awhile too. I would give him some gas meds and a 2-4 ounce bottle and rock him. He would go right back to sleep within about 10 minutes.
If it is teething you could try giving motrin/ibuprophen/advil, it is a little better than tylenol bc it reduces swelling as well as pain and it lasts longer so he can sleep better. If you haven't given him motrin yet tho ask your dr. first if they think it's safe for your baby.
Unless he has any weird allergies or any health problems it should be.
Good Luck!
J.