Douggg, how long was the beast and the False Prophet imprisoned in the Bottomless Pit?
When does Isaiah 24:21-22 take place? How long are the many days that the judged entities in the Isaiah 23:21-22 verse will face before they are punished?
The beast-king and the false prophet are end times persons. They have never been in the bottomless pit prison.
Isaiah 24:21-22 takes place at the time of the great white throne judgment.
The "host (group) of high ones that are on high" in verse 21 is referring to certain of the angels who rebelled with Satan, who committed sex acts with human women back around the time of the flood (Genesis 6:2-4), perverting the human race, resulting in the giants on the earth. And as a result, the earth became filled with violence and evil (Genesis 6:5, Genesis 6:11-12).
Those angels have been imprisoned, Jude 1:6, awaiting the great day of judgment.
Jude 1:6 And the angels which kept not their first estate, but left their own habitation, he hath reserved in everlasting chains under darkness unto the judgment of the great day.
....and will stand before the great white throne judgment - and on that great day will be cast into the lake of fire. As creation will be cleansed of all the evil ones. And creation start afresh in Revelation 21.