Plovdiv city was possibly at times a vassal of Bulgaria or Venice. Ivan Asen II conquered the duchy finally in 1230 but the city had possibly been conquered earlier. Afterwards, Plovdiv was conquered by Byzantium. According to some information, by 1300 Plovdiv was a possession of Theodore Svetoslav of Bulgaria. It was conquered from Byzantium by George Terter II of Bulgaria in 1322. Andronikos III Palaiologos unsuccessfully besieged the city, but a treaty restored Byzantine rule once again in 1323. In 1344 the city and eight other cities were surrendered to Bulgaria by the regency for John V Palaiologos as the
Plovdiv in Silistra Eyalet between 1593 and 1826, the sanjak centre in Eyalet of Adrianople between 1826 and1867 and the sanjak centre of Edirne Vilayet between 1867 and 1878. During that period Plovdiv was a major economic center along with Constantinople, Edirne, and Thessaloniki. The richer citizens constructed beautiful houses many of which can still be seen in the Architectural reserve Old Plovdiv. Under the rule of the Ottoman Empire, Filibe (as the city was known at that time) was a focal point for the Bulgarian national movement and survived as one of the major cultural centers for Bulgarian culture and