The heirs of George Grosz — the painter best known for his affiliation with the Berlin Dadaists — have suffered a setback in their attempt to reclaim three paintings in the collection of the Museum of Modern Art that they claim were looted by Nazis in the 1930s.

Last month, New York judge John McMahon dismissed the heirs’ claims, ruling that they had exceeded the three-year statute of limitations for filing such a suit, the Art Newspaper reports. After first asking for the return of the paintings in 2003, the plaintiffs waited until 2009 before filing suit. McMahon says they should have acted more quickly.

MoMA says it has conducted exhaustive research into the provenance of the paintings — Portrait of the Poet Max Hermann-Neisse (with Cognac Glass) (1927), Self-portrait with a Model (1928), and Republican Automatons (1920) — and believes that the works were never held as Nazi plunder. The museum acquired the three works between 1946 and 1954.