AITOR KARANKA remains hopeful Gaston Ramirez will be confirmed as a Middlesbrough player shortly, and has outlined his intention to make further additions before the end of the transfer window.

Karanka, who has tabled formal offers for Borussia Dortmund defender Neven Subotic and Valencia striker Alvaro Negredo, watched his Middlesbrough side kick off their pre-season programme with a comprehensive 6-0 win at York City on Saturday.

Two of Boro’s summer signings – Marten de Roon and Jordan McGhee – made their maiden appearances in the game, with Victor Valdes and Viktor Fischer expected to be involved in this weekend’s friendly at Doncaster, but Karanka remains keen to recruit at least three more players.

Ideally, one of those will be Ramirez, with a deal having been agreed for the midfielder, who spent the second half of last season on loan at the Riverside.

However, Ramirez’s situation is complicated by the need for a work permit after he signed a pre-contract agreement with Uruguayan side Penarol in January that has now been scrapped.

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Had Ramirez been moving directly from Southampton, he would almost certainly have been granted a permit directly. As it is, however, Boro officials expect their initial approach to the Home Office to be rejected, and are preparing the grounds for an appeal.

“I hope it will all work out, but it is not in our hands,” said Karanka. “He wants to come here, and he knows that I want him here. He knows that the club and the crowd and everybody here wants him, so it’s just for us to wait for his work permit now.

“I can understand that he feels wanted here because he came in January when he was having a bad moment in his career and helped us a lot last season.

“We also helped him a lot, and for that reason he recovered his level. He knows that to keep improving and growing, the best place is here.”

As well as pursuing Ramirez, Karanka is also targeting the addition of a centre-half and centre-forward, with Subotic and Negredo currently topping his wanted list.

Subotic was on Teesside for talks last Wednesday, with Borussia Dortmund having accepted Boro’s offer of around €6m for the Serbian’s services. However, a number of other clubs have now also approached the 27-year-old, with Arsenal and German side Koln understood to be especially keen to sign him.

Boro had been hoping to make progress on the deal over the weekend, but Subotic has indicated that he needs further time to make a decision on his future.

Negredo was the subject of a formal approach at the end of last week, with Valencia willing to sell the 30-year-old, who returned to La Liga in a €27m deal last summer having spent the previous season on loan at the Mestalla from Manchester City.

The Northern Echo: Manchester City's Alvaro Negredo goes on the attack against Newcastle United this season. His club are using Almit Group to improve its training headquarters

Negredo scored 23 goals in 49 appearances during his time with City, but managed just five La Liga goals for Valencia last season as he spent the majority of his time on the substitutes’ bench.

There were weekend reports in Spain suggesting he had turned down the opportunity to move to Teesside, but Boro officials remain hopeful a deal can be brokered.

Karanka, who has also been linked with former Manchester United striker Robin van Persie, remains hopeful of adding to his squad before leaving for a training camp in Marbella at the start of next week.

“It has been great (making five signings) because it shows how well the club is working,” said the Spaniard. “Last summer, we had problems bringing in players at the beginning, but now we have a lot of players arriving and hopefully there will be more arriving soon. The targets are more or less clear, and for that reason I am really pleased.”

Karanka was also satisfied with his squad’s performance at Bootham Crescent as he fielded 22 different players over the course of the 90 minutes.

Boro took the lead through a Scott Flinders own goal – the York goalkeeper inadvertently deflected the ball in after Carlos de Pena’s shot rebounded off the post – and added further first-half goals through David Nugent and Albert Adomah, both of whom looked particularly sharp.

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Jordan Rhodes claimed two goals of his own after the break, with Adam Reach also getting onto the scoresheet with a deft chip, but the game was blighted by the dislocated shoulder that will keep James Husband out of the opening weeks of the season.

Twelve months on from Alex Baptiste’s broken leg at Bootham Crescent, Husband left the ground with his arm in a sling after falling awkwardly close to the corner flag.

“It’s not the same as last season, but we had another injury with Hubby,” said Karanka. “That is the worst thing when you are playing in pre-season. For me, these kind of games are really just a training session, and when you go home with an injury, it is not good.”

Daniel Ayala, who has been the subject of mounting transfer speculation, was not present at York, but Karanka insists the Spanish centre-half was nursing an ankle injury.

“Ben (Gibson, who watched the game from the stands) and Dani are injured,” he said. “Both of them were injured the same day after a training session. He (Ayala) felt his ankle again so both of them are injured.”

Connor Ripley has joined Oldham Athletic on a season-long loan, while Boro have confirmed a home friendly against Spanish side Real Sociedad on Saturday, August 6 (2pm).