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Hello Andrea, you could always set up your flow in such a way that they can only go through it once. That would avoid his e-mail from being used in that flow again, as far as I know. Hope that helps!
If Eduardo's suggestion doesn't work, you can add a filter to the campaign "Member of smartlist not in 'Possible Duplicates'". Note this will remove anyone who is a possible duplicate, even if they haven't received the email before.
If you set up a Marketo Form for your product download request, then you can't create a duplicate lead, as long as the same email address is used--the email address is the unique identifer.
Set up your form, add to a landing page, then run a triggered smart campaign, triggered off of the form fill, and set it up to run only once. Your flow should be to deliver the product and start the drip campaign.