Proceed as follows if you want to remove uploaded files from study lists:
Go to your study list and to the external content. Click on the delete icon (trash can). Your file is then no longer in the study list.
Note:
Your file will then still be available in your own content. If you want to permanently delete a file not only from a learning list but also from your own content, click on "Own content" and on the right on the three dots, then on Delete.