Queen Anne of England died without surviving issue despite 17 pregnancies. Did any other monarch try so hard to produce an heir without success?
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Not an exact fit, but Emperor Renzhong of Song came close with 16 children known to history. All three sons and eight of the daughters died young, so he eventually had to adopt the son of a cousin to succeed him. Though five of his princesses survived to adulthood, they were not considered heirs under Chinese succession laws. In that sense, Renzhong was unsuccessful in producing an heir.
We do know Renzhong tried pretty hard, because he had at least 18 empresses and other concubines who received formal titles on the historical record. Chances are that between them, there was at least 17 total pregnancies, but this is of course impossible to verify today.
Generally speaking, it would be incredibly difficult for one person to be pregnant as many times as Queen Anne was. Hence male monarchs with harems were more likely to have exceeded her count, but conversely, the historical record on pregnancies of consorts or concubines are rather less than meticulous.
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