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Kinase Chemistry – Just a year and a half behind the times.

WO2007011065

Posted by kinasepro on January 28, 2007

Mitsubishi has an app covering the intermediates for their GSK3 Sanofi-Aventis stuff. I still think the spiro compounds are sexier, but the morpholines are further explored so here we have a pretty solid looking asymmetric method to make 2-aryl morpholines via CBS reduction:

FC1=CC=C(C(CCl)=O)C=C1 FC1=CC=C([C@H](O)CCl)C=C1
FC1=CC=C([C@H](O)CNCC2=CC=CC=C2)C=C1 FC1=CC=C([C@H](OC2)CN(CC3=CC=CC=C3)C2=O)C=C1
FC1=CC=C([C@H]2CN(CC3=CC=CC=C3)CCO2)C=C1 FC1=CC=C([C@H]2CNCCO2)C=C1
Route starts on page 79 example 1, 2 & 5 shown here.

Array might have something to say with how novel the approach is, y’know given how they sell the (rac) stuff?

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2 Responses to “WO2007011065”

  1. kinasepro said

    Its wishful thinking, but I personally hope that KSR v. Teleflex kills the need for these kinds of patent apps.

  2. milkshake said

    Process people like to patent procedures even if the patent is screemingly obvious piece of work precedented in literature. I spoke with paul Raider (when he was at Merck)and he said they would use these process patents to protect themselves against somebody elese patenting their work and then extorting hem. He said they also use this kind of patents as leverage when negotiating with other companies who hold patent on similar things, which would be good to licence. Then during license negotiations they could say: “We are not going to pay for your catalyst this ridiculous money that you are asking – look at out own patents, we have catalyst that gives 94% ee instead of your 98% ee but this would be good enough for us.”

    By the way, for these chloroacetophenones there is a much better method than CBS reduction. It is the Noyori transfer hydrogentation withe RuCl2(cymene)/TsDPEN – you can do it at room temp and it is insensitive to water. I think the actual reason they did not use it is that Noyori patented his catalysts quite thoroughly…

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