A Wikipedia list suggests that the earliest deemed English chartered trade monopoly organization was The Company of Merchant Adventurers of London in 1407 and presumably most, if not nearly all, became defunct by the 20th century. Between that period, there were hundreds if not thousands of various monopoly charters granted by the English and Scottish crowns.
Because it's easy to profit with legal monopoly over a product with heavy demand, these companies should have financially thrived. Save for theft and other corruption, which were not uncommon, what were the primary causes of the monopoly charters to fail or otherwise lose their chartered monopolies?