Ivan Asen II of Bulgaria
In 1225, the city was captured by the ambitious Greek ruler of Epirus and Thessalonica, Theodore Komnenos Doukas, but after his defeat and capture at the Battle of Klokotnitsa in 1230 it fell to Ivan Asen II of Bulgaria. As such, "Dimotiko" is mentioned in a grant of trading privileges issued by Ivan Asen to the Republic of Ragusa.