The first case was acquired in 2015! Shire acquires NPS for $5.2 billion
Just as biopharmaceutical industry analysts look back on the wave of mergers and acquisitions in the pharmaceutical industry in 2014, Shire has quietly reached an acquisition agreement with the famous rare drug developer NPS Pharmaceuticals. This is also the first pharmaceutical acquisition in the media in 2015, suggesting that the capital operation of the biopharmaceutical industry will remain a theme in 2015.
According to the news, Shire will buy NPS at a premium of 51% based on the NPS share price, and acquire NPS at a price of US$46 per share. The entire agreement is as high as $5.2 billion. Through this merger, Shire will include NPS's Rare Drugs R&D department, which is an important part of Shire's future development strategy.
Sight back to 2014, Aibowei has been close to Shire to reach a multi-billion dollar merger agreement, but with the Obama administration's tightening of bio-pharmaceutical companies' overseas merger policy, the merger case Dead belly. Prior to this, as a biopharmaceutical company in Ireland, the lower tax rate of Shire's location made Shire the scent of many biomedical giants. However, with the US government's counterattack, Shire's acquisition value has also shrunk. But this does not mean that Shire will do nothing in the new year. In fact, Shire’s new CEO, Flemming Ornskov, has long been known for promoting Shire’s mergers and acquisitions business.
On the other hand, Pfizer, which is very active in the acquisition market in 2014, also sent a signal of unwillingness. Following the failure of Pfizer's attempt to acquire AstraZeneca for $117 billion in 2014, Pfizer has been looking for other potential acquisition targets. It is reported that Pfizer has listed Aibowei, GlaxoSmithKline, Bristol-Myers Squibb and Actavis as possible merger targets. If the news is true, Pfizer will surely set off a wave of turmoil in the biomedical market in 2015.
Preparation of Fenebute
1. Prepare the first intermediate
Benzaldehyde and ethyl acetoacetate into ethanol, stir at room temperature under the catalysis of organic alkali reaction with filter cake filtration after 45 ~ 50 h, after the completion of the filter with ethanol elution filter cake, dry cake solids, then ethanol filtrate concentrated to a quarter of the original volume, to cold, concentrate filtering alcohol washing, solid, merging two solid is the first intermediate; The mole ratio of benzaldehyde, ethyl acetoacetate and ethanol is 1:2.5 -3:12-15.
2. Prepare the second intermediate
The first intermediate is added to the mass concentration of 20% sodium hydroxide solution, and the reaction is stirred at 85-90°C for 2-5 hours. After filtration, the filter cake is used for filtration. After filtration, the filter cake is washed, the filtrate is combined and cooled, and the filtrate is cooled by stirring for 3h. Solid second intermediate; The mass ratio of the first intermediate to the sodium hydroxide solution is I: 1.8-2.0;
3. Prepare the third intermediate
The second intermediate was dissolved in pure acetic anhydride solution for reflux 3 ~ 5h. After the reflux, the acetic anhydride was concentrated and dissolved with toluene. After the dissolution, ammonia water was added, and the reaction took place at 60_65°C for 1 ~ 1.5 h. Filtrate, wash and dry the precipitated solid to get the solid third intermediate; The mass ratio of the second intermediate, pure acetic anhydride solution, toluene and ammonia water is 5:1-1.2:0.5-0.8:0.5-0.8;
4. Prepare Finebute
The third intermediate was dissolved in 25% sodium hydroxide solution and cooled to _5°C ~ 10°C. After cooling, sodium hypochlorite was added slowly within 15-20min for 1h reaction, followed by ice bath reaction of 0.5 ~ 1.5 h and water bath reaction of 0.5 ~ 1.5 h. Finally, the temperature was gradually increased to 60 ~ 80°C for 1-5 h, and the reaction was cooled again after completion. After cooling, hydrochloric acid was added in the ice water bath to adjust the PH to 2, and the decolorization was stirred at room temperature. After filtration, sodium hydroxide was added in the ice water bath to adjust the PH to 6-7, and the cooling was stirred for 2 hours. The mass ratio of the third intermediate, sodium hydroxide solution and sodium hypochlorite is 1.0:0.8-1.0:1.0-1.1.
Preparation of Fenebute
1. Prepare the first intermediate
Benzaldehyde and ethyl acetoacetate into ethanol, stir at room temperature under the catalysis of organic alkali reaction with filter cake filtration after 45 ~ 50 h, after the completion of the filter with ethanol elution filter cake, dry cake solids, then ethanol filtrate concentrated to a quarter of the original volume, to cold, concentrate filtering alcohol washing, solid, merging two solid is the first intermediate; The mole ratio of benzaldehyde, ethyl acetoacetate and ethanol is 1:2.5 -3:12-15.
2. Prepare the second intermediate
The first intermediate is added to the mass concentration of 20% sodium hydroxide solution, and the reaction is stirred at 85-90°C for 2-5 hours. After filtration, the filter cake is used for filtration. After filtration, the filter cake is washed, the filtrate is combined and cooled, and the filtrate is cooled by stirring for 3h. Solid second intermediate; The mass ratio of the first intermediate to the sodium hydroxide solution is I: 1.8-2.0;
3. Prepare the third intermediate
The second intermediate was dissolved in pure acetic anhydride solution for reflux 3 ~ 5h. After the reflux, the acetic anhydride was concentrated and dissolved with toluene. After the dissolution, ammonia water was added, and the reaction took place at 60_65°C for 1 ~ 1.5 h. Filtrate, wash and dry the precipitated solid to get the solid third intermediate; The mass ratio of the second intermediate, pure acetic anhydride solution, toluene and ammonia water is 5:1-1.2:0.5-0.8:0.5-0.8;
4. Prepare Finebute
The third intermediate was dissolved in 25% sodium hydroxide solution and cooled to _5°C ~ 10°C. After cooling, sodium hypochlorite was added slowly within 15-20min for 1h reaction, followed by ice bath reaction of 0.5 ~ 1.5 h and water bath reaction of 0.5 ~ 1.5 h. Finally, the temperature was gradually increased to 60 ~ 80°C for 1-5 h, and the reaction was cooled again after completion. After cooling, hydrochloric acid was added in the ice water bath to adjust the PH to 2, and the decolorization was stirred at room temperature. After filtration, sodium hydroxide was added in the ice water bath to adjust the PH to 6-7, and the cooling was stirred for 2 hours. The mass ratio of the third intermediate, sodium hydroxide solution and sodium hypochlorite is 1.0:0.8-1.0:1.0-1.1.
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