It is not possible to change the callback URL in the manner you mentioned for new package push upgrades. See this document where it states
For your convenience, you can update some fields in a connected app
and the changes apply immediately to all installed versions of the
app. For example, connected app descriptions are immediately updated
in each version of the connected app. The following
version-independent fields bypass the packaging or installation
lifecycle.
Description
Info URL
Logo Image URL
Callback URL
You can though specify multiple callback URLs for every connected app with effect as per these rules.
Here's another thread which confirms wildcards are not supported.