What are the correct sentences?

1.?He used to run his dog up to the extent that it was tired.

2.?He used to swim his dog up to the extent that it was tired. ?

3.He used to walk his dog up to the extent that it was tired.

??4.?He used to run up his dog to the extent that it was tired.

5.?He used to swim up his dog to the extent that it was tired. ?

6.He used to walk up his dog to the extent that it was tired.

What are the correct sentences?