Police in North Macedonia said 47 officers were hurt, two of them seriously, after a group of mostly young people threw stones, metal bars, eggs and Molotov cocktails at the parliament building in the capital.
Thousands of people have protested nightly in Skopje since the weekend over a French proposal for a compromise aimed at lifting objections by neighbouring Bulgaria to North Macedonia joining the European Union (EU).
Police said 11 protesters were detained on Tuesday night, when the officers were injured.
Prime Minister Dimitar Kovacevski condemned the attacks on the police, saying violence cannot be justified.
Another protest is planned for Wednesday evening.
Bulgaria, which as an EU member has veto powers over new members, wants North Macedonia to formally recognise its language has Bulgarian roots, to recognise a Bulgarian minority in the country and to quash “hate speech” against Bulgaria.
Many in North Macedonia say acquiescing would undermine their national identity.
North Macedonia’s president, Stevo Pendarovski, and the government back the proposed French deal, which calls for the country to acknowledge in its constitution the existence of an ethnic Bulgarian minority.
It would also provide for regular reviews on how the bilateral dispute is being addressed, which could potentially hamper North Macedonia’s future course toward EU membership.
Bulgaria has already formally accepted the French proposal, which now requires the backing of North Macedonia’s parliament.
Politicians are set to convene later this week.
The centre-right main opposition party VMRO-DPMNE, many international law experts and civic organisations counter that the French proposal favours Bulgarian demands, which dispute Macedonian views of regional history, language, identity and heritage.
North Macedonia has been a candidate for EU membership for 17 years.
The country received a green light in 2020 to begin accession talks, but no date for the start of the negotiations has been set.