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| 223–187 |
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| ANTIOCHUS III, THE GREAT, brother of Seleucus III, regained from Attalus most of the territory lost since 241. He recovered the Mesopotamian provinces from the revolting governor, Molon (221). | 1 |
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| 221–217 |
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| Fourth Syrian War. Antiochus III's initial successes were followed by his defeat at Raphia (217), and Antiochus retained only Seleucia, the port of Antioch on the Syrian coast. | 2 |
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| 212–205 |
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| Anabasis of Antiochus III. In a series of victorious campaigns, Antiochus compelled Arsaces III of Parthia to pay tribute, formed an alliance with Euthydemus of Bactria, and made a treaty with the Indian ruler Sophagaesenus (See 206). Thus he consolidated Seleucid power in the east for a time. | 3 |
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| 202–200 |
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| The Fifth Syrian War resulted from the treaty between Antiochus III and Philip V of Macedon. The war was decided by Antiochus's victory of Panium whereby he secured from Egypt most of Coele-Syria and southern Asia Minor (save Cyprus). | 4 |
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| 197–194 |
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| Antiochus then campaigned in Asia Minor and Thrace, causing Eumenes II Sotor of Pergamum (197–159) to complain to Rome. Diplomacy failed to resolve Rome's dispute with Antiochus (194–192). | 5 |
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| 192–189 |
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| WAR WITH ROME broke out when Antiochus crossed to Greece to aid the Aetolians and the Romans declared war. The forces of Antiochus were driven from Greece (191) and his fleet was defeated at Myonnesus (190). The Roman army entered Asia Minor and defeated Antiochus himself at Magnesia (190). In the peace of Apamea (188), Antiochus paid a large indemnity, lost his fleet, and surrendered Asia Minor, which was divided between Rhodes and Pergamum. This defeat led to the complete breaking away of Armenia (under Artaxias) and of Bactria. | 6 |
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| 187–175 |
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| Seleucus IV Philopater (“loving his father”) succeeded Antiochus III, and during his reign the empire gradually recovered strength. Meanwhile Eumenes II of Pergamum successfully fought against Prusias I of Bithynia (187–183) and Pharnaces I of Pontus (183–179). | 7 |
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| 175–163 |
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| Antiochus IV Epiphanes (“god manifest”) succeeded upon the murder of his brother Seleucus. Though friendly to Rome, he was prevented by the Romans from concluding successfully the Sixth Syrian War against Egypt (170–168). The Romans also weakened Rhodes by making Delos a free port (167). | 8 |
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| 168–163 |
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| Dissent between Hellenized and observant Jews caused violence in Jerusalem that Antiochus suppressed with force and repression. Led by Judas Maccabeus, the Jews began a successful guerrilla war (168). A large Seleucid army forced negotiations, and, as a result, the temple fortifications were dismantled and Jewish religious freedom was restored (163). | 9 |
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| 164–162 |
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| Antiochus V Eupator, with Lysias as regent, succeeded his father Antiochus IV, who died campaigning against the Parthians. | 10 |
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| 162–150 |
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| Demetrius I Soter, son of Seleucus IV, returned from Rome and executed Antiochus but was himself defeated and killed in 150 by a pretender, Alexander Balas (150–145). In 145 Alexander was defeated by the son of Demetrius I who ruled as Demetrius II Nicator. | 11 |
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| 145–139 |
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| Demetrius II Nicator. Demetrius was challenged by several usurpers. In 142 Demetrius made an alliance with Simon Maccabeus who established an independent Jewish state under the Hasmonean dynasty. His successors—John Hyrcanus (134–104), Judah-Aristobulus (104–103), and Alexander Jannaeus (102–76)—took advantage of the weakness of Seleucid rulers to extend the power of the Jewish state. Meanwhile in 139 Demetrius was captured by Mithridates I of Parthia and was succeeded by his younger brother, Antiochus VII Euergetes Eusebes Soter Sidetes. | 12 |
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