Abstract
According to the set objectives, the authors of the paper have all the known data from written sources about the medieval town Prilep, which we know for sure that it was placed in the Drina parish of Bistrica, in an appropriate historical context. In this way, a contribution was made through the valorization of the importance and role of this city in the historical development of the Upper Drina region and the wider area during the 14th and 15th centuries. In addition, considering the observed similarity in toponymy with the town of Prilep near Novo Brdo, an analysis and comparison of several toponyms in Upper Podrinje with those from the wider area of Novo Brdo was carried out. Studies have showed their connection during the middle age although it was about relatively distant regions. On the one hand, this is understandable because both belonged to the same ethnic and cultural-historical space. Especially since Upper Podrinje was an integral part of the Raška medieval state until 1373, which also included the Novo Brdo region. Also, studies have shown a possible connection through the noble family of Kosač, whose progenitor, as it seems, for a time actually resided in the Novo Brdo region serving at the court of the Serbian emperor.

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