The Borderland
The Borderland was a lawless region of space between the Klingon Empire and the Orion Syndicate in the mid-22nd century.
In 2154, a Klingon Bird-of-Prey was commandeered by almost twenty Human Augments in the Borderland. The Enterprise subsequently entered the region to search for them in the hopes of bringing the Augments to justice and avoiding an interstellar war with the Klingons, who blamed Earth for the deaths of the Bird-of-Prey's crew. While searching for the Augments, Enterprise was attacked by two Orion interceptors, who abducted nine members of the Enterprise crew. The captives were subsequenly taken to Verex III, a planet in the Borderland, where they were to be auctioned off as slaves. Eventually, Captain Archer was able to recover his missing crewmembers with the assistance of Arik Soong, who had spent time in the Borderland and had experience dealing with the Orions. (ENT episode: "Borderland")
In 2159, the IKS SuHDah went missing in the Borderland. 227 years later Federation probes found the IKS SuHDah abandoned in the Borderland, over two hundred years old. Starfleet sent the USS Intrepid-A to the Borderland to find out what happened to the crew of the IKS SuHDah. It was revealed that the IKS SuHDah was attacked by a Der'kal warship. (Star Trek: Kingston episode: "The Discovery")