To avoid such disputes and to assure Spain of an ally in Italian affairs Charles I and Philip II bent their efforts to procure the election of popes who would be favorable to them. Charles had much to do with the choice in 1522 of Adrian VI, who as a cardinal had been one of his principal administrative officers during his own absence from the peninsula in the early years of his reign. Philip was successful in the same way when in 1559 he was able to cause the elevation of his candidate to the papal throne. This pope, Pius IV, proceeded to annul the action of his predecessor, Paul IV, against Charles and Philip, and condemned to death two members of the deceased pope’s family, one of them a cardinal. At the election of 1590 Philip was again fortunate, but the new pontiff, Urban VII, lived only thirteen days. A fresh conclave was held, at which Philip went to the extreme not only of excluding the candidates whom he opposed but also of naming seven Spanish churchmen as the only ones from among whom the cardinals were to choose. One of the seven was elected, taking the name Gregory XIV, and no pope of the century was more unconditionally favorable to the wishes of a Spanish king. This constant intrusion of Philip ended by exasperating the high authorities of the church, who a few years later under another pope condemned Philip’s practices and declared him _ipso facto_ excommunicated. This proved to be a decisive blow to the influence of the Spanish crown. [Sidenote: The _pase regio_ as an aid to the kings in the conflict with the popes.]