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BERLIN — Germany says it won’t return two paintings once owned by a Jewish businessman who fled the Nazis, even as the western city of Cologne agreed to hand back almost a dozen other valuable drawings to heirs in two separate cases.

The contrasting decisions were both announced Wednesday. They illustrate the considerable legal leeway that German officials have when it comes to deciding on claims by the descendants of Jewish collectors persecuted by Adolf Hitler’s regime, as they struggle to find a solution for the vast trove of art discovered in a Munich apartment.

The Finance Ministry said its refusal to cede two works by 18th-century painter Bernardo Bellotto to the grandchildren of deceased businessman Max Emden was due to the fact that the Jewish collector had managed to take them with him when he emigrated from Germany in 1933 — the year Hitler came to power.

“Both the seller (Emden) and the paintings were in Switzerland at the time of the sale,” the ministry said in a statement sent to The Associated Press. This, it said, meant the paintings couldn’t be considered “looted art” or lost in some other way as a result of Nazi persecution.

Emden’s heirs maintain that their grandfather sold the paintings because he needed money after his businesses in Germany were seized by the Nazis.

“The Zwinger Moat in Dresden” is currently on exhibit at the city’s Museum for Military History, while a panorama that Bellotto painted of Vienna is in storage at the Kunstpalast museum in Duesseldorf.

The federal government’s decision was published within hours of an announcement by the city of Cologne, saying it would return 11 avant-garde and modernist drawings to the heirs of Jewish collectors who sold them before or shortly after fleeing Nazi Germany.

City counselors voted late Tuesday to hand six drawings by Karl Hofer, Paula Modersohn-Becker, Ernst Barlach, Aristide Maillol and Wilhelm Morgner to the heirs of Jewish collector Alfred Flechtheim, who fled to France in 1933.

It also returned five drawings by Ernst Ludwig Kirchner, Erich Heckel and Georges Kars to the heirs of Curt Glaser, another Jewish collector who emigrated in 1933.

Both sets ended up in Cologne’s Museum Ludwig, which has reached an agreement with the new owners to continue exhibiting the drawings.

A spokeswoman for the city of Cologne, Inge Schuermann, said in each case negotiations with the heirs had been marked by “respect and fairness.”

Last month’s revelation that an octogenarian recluse in Munich had for decades hoarded hundreds of valuable works by artists such as Max Liebermann, Otto Dix and Marc Chagall in his Munich apartment has once again put a spotlight on the issue of Nazi-looted art in Germany.

Authorities stumbled across the art almost by chance in 2012, but kept the find secret until it was publicized last month by the German magazine Focus.

The German government subsequently came under intense pressure from Jewish groups to expedite its probe into the case and honor legitimate claims to the works. But progress has been partly hindered by legal difficulties, including a 30-year-statute of limitations.

Officials have said they are examining all options, including appealing to the art’s current owner, Cornelius Gurlitt, to show goodwill toward the heirs.

“All possibilities are being discussed with Mr. Gurlitt,” said Hagen Philipp Wolf, a spokesman for the federal government’s culture office. “This naturally includes the option of handing the works to the state.”

If this were to occur, the heirs of former owners would have to hope the German government takes a more favorable view of their claims than it did to those of the Emden family.

“There’s been zero goodwill by the German government,” Emden’s grandson Juan-Carlos said in an interview from his home in Chile.

His lawyer, Mel Urbach, told the AP last month that he hoped the German government would agree to let the case go before a special expert commission appointed to deal with such disputes.

In its statement Wednesday, the Finance Ministry made clear this wasn’t an option.