An Orthodox businessman has lost a High Court action involving a bitter family feud over the carve-up of assets from a multi-million pound property empire.

Joseph Ackerman sued his sister-in law Naomi Ackerman and her son Barry Ackerman in a case which has racked up estimated costs of £2 million.

Mr Ackerman and his brother Jack, who arrived as child refugees in the UK from Czechoslovakia in 1941, built up a flourishing property business. They also established a charity, Delapage, aiding Orthodox causes.

After Jack's death in 1989, Joseph Ackerman continued to run the Ackerman Group, in Hendon, north-west London. In 2001, one of Naomi's five children, Barry, came to work for it part-time but he and Joseph did not "see eye to eye," according to Chancery judge Mr Justice Vos.

"From 2004 onwards, relationships between the two branches of the family deteriorated steeply and became extremely acrimonious," the judge said.

In 2006, Naomi and Joseph Ackerman decided to go their separate ways and asked a tax QC, Andrew Thornhill, to arrange a division of the assets.

In January this year, Mr Thornhill determined that all joint companies should be transferred to Naomi, including a number originally set up to aid Joseph's four children. Joseph, he said, owed her £20 million. While, according to one estimate, the assets were worth more than £400 million on paper, Mr Thornhill concluded that the property group was insolvent and, in the judge's words, "could not survive without a major debt rescheduling".

Last year, the Charity Commission ordered an inquiry and put in managers to oversee Delapage, which is owed nearly £100 million in loans and interest from other companies.

But Joseph Ackerman disputed Mr Thornhill's decision, issuing proceedings also against the barrister on the grounds that he had acted unfairly.

Mr Ackerman was absent from the 11-day hearing - his counsel Neil Kitchener QC suggesting "that it would have made future reconciliation between these warring parties, more, not less, difficult, had Joseph given evidence or attended the trial."

Joseph Ackerman's son-in-law Danny Wulwick, described as his assistant and confidante, did give evidence. But Mr Justice Vos concluded: "I am satisfied that Joseph's and Danny's conduct towards Barry and Naomi in the de-merger process was wholly unreasonable and obstructive."

The judge said that Joseph Ackerman "came close to making Mr Thornhill's task impossible". Although the barrister had behaved unwisely in "a number of minor respects" the judge found, he had always acted fairly, faced with "the most acrimonious dispute of a life time".