MySQLのDELETE文ではexistsやサブクエリを使えないので複数DELETE構文を使う。
下記は重複したデータのうち古い方を消すクエリ
```
delete target from user_companies target, user_companies sub
where
target.user_id = sub.user_id
and target.company_id = sub.company_id
and target.send_permitted = sub.send_permitted
and target.created_at < sub.created_at;
```