Open slddrw, create PDF and overwrite existing PDF

I am currently working on a workflow that collects approvals from multiple people and stamps them to the data card.  After these approvals are collected I need to automatically check out the drawing to populate the approval fields on the drawing.  I then need to create a new PDF containing the approvals and overwrite the existing PDF in the same folder. Has anyone done this?

SolidworksSolidworks Pdm enterprise Pdm