In 1330, the Serbs defeated the Bulgarians in the vicinity, effectively keeping the region to the Serbian Kingdom. Serbian magnate Dejan, one of the prominent figures of the Serbian Empire and its subsequent fall, had initially held a large province in the Kumanovo region under Dušan, and was later as "despot" under Uroš V assigned the Upper Struma river with Velbuzhd. Upon Dejan's death, his possessions in Žegligovo and Upper Struma were given to his two sons, Jovan Dragaš (d. 1378) and Konstantin (d. 1395). The Dejanović brothers ruled a spacious province in eastern Macedonia, in the southern lands of the Empire, and remained loyal to Uroš V, until 1373, when Orhan Gazi's Ottoman army compelled Jovan to recognize Ottoman vassalage.