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A new crystal form II on Apremilast

Times:2015-06-13

 We are planning to transfer the right of patent application on the crystal form II of Apremilast (CN104761484A, PCT/CN2015/000566)to companies who are interested in it. And we would like to offer you Crystal form II as free sample if you really interested in our patent. Pls contact with us for more information.
 Apremilast (brand name Otezla), which is developed by Celgene, is an orally available small molecule inhibitor of phosphodiesterase 4 (PDE4). Apremilast specifically inhibits PDE4 and inhibits spontaneous production of TNF-alpha from human rheumatoid synovial cells. It has anti-inflammatory activity. Apremilast was approved by FDA and EMEA for the treatment of psoriatic arthritis and psoriasis in 2014. It is also being tested for its efficacy in treating other chronic inflammatory diseases such as ankylosing spondylitis, Behcet's disease, andrheumatoid arthritis,etc. Its sales revenue in the year of 2020 is expected to be 2 billion USD.In addition,  Apremilast receives the Orphan Drug Designation (ODD) from FDA as well as EMEA for the treatment of Behcet's disease.
 
The compound patent will expire on November 2019. However, Celgene applied for crystal form patent WO2009120167, involving 7 different crystal forms (A, B, C, D, E, F and G). This crystal form patent has been approved in US(US7893101), Europe(EP2276483), Japan(JP5474043 ),etc. Its priority date started from March 2008, and will expire in March 2028. According to Celgene’s report, crystal form B is the most stable crystal form among the 7 different crystal forms (A, B, C, D, E, F and G)and is used in the formulation product.
 
Now we found a totally new and more stable crystal form of Apremilast and applied patents(CN201510101009, PCT/CN2015/000566) on it, making it possible that your company could bring the related generic drug to market after Celgene's compound patent expires on November 2019. It's 9 years earlier than 2028, which means billion USD business for you.
 
Here please find more technical details on the new crystal form:
We named the new crystal form of Apremilast as crystal form II. Its X-ray powder diffraction is completely different from A, B, C, D, E, F and G reported by Celgene company and its DSC spectrum exhibits a single peak about 150℃ and its TG spectrum show a mass loss of less than about 0.5% when heated from about 25℃ to 150℃. Our study confirmed that the crystal form II is more stable than the crystal form B because B will be partially converted to II in water at 60-100℃. Moreover, we found a method to completely transfer Celgene's crystal form B and D(other crystal form should be also ok) to the crystal form II in certain solvent without dissolving, and this further proves that the crystal form II is more stable than crystal form B. There are almost no difference in solubility in all kinds of solvents between II and B.
 
Recently we performed comparison experiment on rats, and the absorption of those 2 crystal forms are very silimar, except stronger activity(about 1.5 times) of Crystal form II in female mouse. In addition, we got the similar result of the two crystal form in dogs. We will confirm this in next stage experiments.

Here please also find Celgene's crystal form patents in different countries:
WO2009120167 
SI2276483 (T1)   RU2010143907 (A)   RU2471782 (C2)   PT2276483 (E)   NZ588104 (A)   NO2015017 (I1)   MX2010010454 (A)   KR20150038547 (A)   KR20140142323 (A)   KR20100132045 (A)   JP2011515463 (A)   JP5474043 (B2)   HRP20140609 (T1)   ES2476252 (T3)   EP2695616 (A1)   EP2276483 (A1)   EP2276483 (B1)   DK2276483 (T3)   CN102046167 (A)   CA2718601 (A1)   BRPI0822398 (A2)   AU2008353468 (A1)   AU2008353468 (B2)  

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