‘At the time appointed he will return and come into the south, but it will not be in the latter time as it was in the former. For ships of Kittim will come against him.'
We are not being given the whole history of war between Egypt and Syria and some of it is now skipped over. What mattered to the author was the parts that affected God's purposes. For what now took place was at the appointed time. Antiochus' destiny was in God's hands.
He thought once more to invade Egypt (in 168 BC), and at first met with success, reaching Alexandria, but then he met up with the power that had destroyed his father, the might of the fourth empire, represented here by the might of Rome. Before this he could do nothing.
‘Ships of Kittim.' Compare Numbers 24:24. Kittim in fact denotes Cyprus, from which possibly some of the Roman fleet sailed, although it may only be that it represented ‘the Roman world across the seas', Cyprus being the nearest point known to them. So this was in fact the Romans (LXX reads ‘and the Romans will come') under Gaeus Popilius Linus who sailed to Egypt to prevent his activities. Egypt had clearly made some kind of treaty with Rome. He met with Antiochus and demanded that he should withdraw and did so in a humiliating way. He had no doubts that Antiochus would do so.
Antiochus was furious, but he had no option except to withdraw, for he was no match for Rome, and, determined to avenge himself on the annoying people who were continually thwarting his wishes, and to seize further treasures, he turned his anger on Israel.