The EU has sent a tough message to President Vladimir Putin that it will keep up the pressure over Ukraine by slapping sanctions on three Russian military leaders, prominent Ukrainian separatists, and a popular singer known as Russia’s Frank Sinatra.

The sanctions, officially termed “restrictive measures in respect of actions undermining or threatening the territorial integrity, sovereignty and independence of Ukraine”, were imposed on 19 individuals and nine organisations on Monday, despite last week’s Minsk peace deal and a shaky weekend ceasefire in eastern Ukraine.

The Russian foreign ministry reacted angrily, calling it “clumsy” in the context of last week’s ceasefire deal. The ministry dismissed the new EU sanctions as “running against common sense” and harming chances “to resolve an internal Ukrainian conflict.”

Topping the names added to the list of those subject to travel bans and asset freezes are two Russian deputy defence ministers, Arkady Bakhin and Anatoly Antonov, who, according to the EU, were “involved in supporting the deployment of Russian troops in Ukraine”. Russia denies deploying troops in Ukraine.

Also sanctioned was Andrei Kartapolov, director of the main operations department and deputy chief of the general staff of the armed forces of the Russian Federation. “In both capacities he is actively involved in shaping and implementing the military campaign of the Russian forces in Ukraine” the EU said.

“According to the stated activities of the general staff, by exercising operational control over the armed forces, he [Kartapolov] is actively involved in shaping and implementing the Russian government policy threatening the … independence of Ukraine,” it said.

The EU also listed 14 Ukrainians, all military or political figures in the self-declared republics of Donetsk and Lugansk, as well as nine entities or organisations. They included Pavel Dremov, aka “Batya”, who was described as the commander of the armed separatist First Cossack Regiment and Arseny Pavlov, aka “Motorola”, commander of the Sparta regiment.

Targeted civilians included Alexandr Shubin who, in the EU’s scornful words, is the “so-called minister of justice of the illegal, so-called Luhansk People’s Republic”, and Sergey Litvin, “so-called deputy chairman of the council of ministers”.

Among organisations placed under sanctions was the “public movement” Novorossiya (New Russia), which was established in November 2014. The EU statement suggested that the group was a front for the main intelligence directorate of the Russian general staff and was led by a Russian intelligence officer, Igor Strelkov. Its purpose, it said, was to assist militia fighting in eastern Ukraine.

Two members of the Russian parliament (Duma) were included in the new sanctions list – Valery Rashkin and Joseph Kobzon. Rashkin, first deputy chairman of Duma’s committee on ethnicity issues, is described as the founder of the civil movement Krassnaya Moskva (Red Moscow – Patriotic Front Aid) which organised public demonstrations supporting separatists.

Kobzon is a more colourful figure, known in Russia for his long Soviet-era career as a singer whose repertoire brought comparisons with Sinatra. Born in Chasiv Yar, in the Donbass region of eastern Ukraine, Kobzon rose to national prominence during Leonid Brezhnev’s time at the helm of the former Soviet Union, and was a popular act at official concerts. In 1980, he was honoured as “people’s artist of the USSR”.

Kobzon was the first celebrity to visit Chernobyl after the 1986 nuclear disaster, and was famed for entertaining Russian troops stationed in conflict zones including Afghanistan and Chechnya.

It was his visit last year in support of separatist fighters in Donetsk, and his appointment as honorary consul of the self-declared Donetsk republic, that earned him the EU’s displeasure. Like Rashkin, he has also been penalised for voting for Russia’s annexation of Crimea.

The new sanctions list was agreed by EU foreign ministers last month after separatist attacks on the port city of Mariupol that killed more than 30 civilians. But implementation was delayed pending the outcome of the Minsk peace talks.

By deciding to proceed, the EU appeared to be signalling its determination to punish the separatists for the Mariupol attacks and to maintain pressure Moscow to honour the peace deal.

A total of 151 individuals and 37 organisations have been sanctioned since the EU started taking active measures after the March 2014 annexation of Crimea. Additional economic sanctions were imposed after the shooting down of Malaysia Airlines flight MH17 over Ukraine in July.

Russia’s representative to the EU, Vladimir Chizhov, said the extension of sanctions would undermine the Minsk deal. “This will not only give a signal to Russian public opinion and force Russia to return to our own sanctions list, but will dissuade both sides of the conflict from the active implementation of the provisions of the Minsk documents,” he said.