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    Home > Active Ingredient News > Drugs Articles > Star drug-the tortuous road to market for ibrutinib

    Star drug-the tortuous road to market for ibrutinib

    • Last Update: 2021-03-22
    • Source: Internet
    • Author: User
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    As the first Bruton's tyrosine kinase (BTK) inhibitor, Ibrutinib became one of the fastest-growing anti-tumor drugs within one year after it was launched in the United States in 2013.
    The drug is also an irreversible inhibitor that binds to BTK in the form of a covalent bond.
    This rare combination has also become a model for drug design.
    Last week, we sorted out the basic situation of the drug, and today we take a closer look at the twists and turns of its listing.

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    As the first Bruton's tyrosine kinase (BTK) inhibitor, Ibrutinib became one of the fastest-growing anti-tumor drugs within one year after it was launched in the United States in 2013.
    The drug is also an irreversible inhibitor that binds to BTK in the form of a covalent bond.
    This rare combination has also become a model for drug design.
    Last week, we sorted out the basic situation of the drug, and today we take a closer look at the twists and turns of its listing.

    641px;height:1px;background-image:none;background-color:#374AAE;color:#FFFFFF;overflow:hidden;">
    75em;letter-spacing:1.


    5px;font-size:14px;color:#000000;">

    As the first Bruton's tyrosine kinase (BTK) inhibitor, Ibrutinib became one of the fastest-growing anti-tumor drugs within one year after it was launched in the United States in 2013.
    The drug is also an irreversible inhibitor that binds to BTK in the form of a covalent bond.
    This rare combination has also become a model for drug design.
    Last week, we sorted out the basic situation of the drug, and today we take a closer look at the twists and turns of its listing.

    75em;letter-spacing:1.
    5px;font-size:14px;color:#000000;">

        

    As the first Bruton's tyrosine kinase (BTK) inhibitor, Ibrutinib became one of the fastest-growing anti-tumor drugs within one year after it was launched in the United States in 2013.
    The drug is also an irreversible inhibitor that binds to BTK in the form of a covalent bond.
    This rare combination has also become a model for drug design.
    Last week, we sorted out the basic situation of the drug, and today we take a closer look at the twists and turns of its listing.

        

        

    As the first Bruton's tyrosine kinase (BTK) inhibitor, Ibrutinib became one of the fastest-growing anti-tumor drugs within one year after it was launched in the United States in 2013.
    The drug is also an irreversible inhibitor that binds to BTK in the form of a covalent bond.
    This rare combination has also become a model for drug design.
    Last week, we sorted out the basic situation of the drug, and today we take a closer look at the twists and turns of its listing.

    As the first Bruton's tyrosine kinase (BTK) inhibitor, Ibrutinib became one of the fastest-growing anti-tumor drugs within one year after it was launched in the United States in 2013.
    The drug is also an irreversible inhibitor that binds to BTK in the form of a covalent bond.
    This rare combination has also become a model for drug design.
    Last week, we sorted out the basic situation of the drug, and today we take a closer look at the twists and turns of its listing.
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    75em;text-align:center;box-sizing:border-box ;overflow-wrap:break-word ;'>  Figure 1.
    Schematic diagram of the role of ibrutinib in the B cell signaling pathway  Figure 1.
    Schematic diagram of the role of ibrutinib in the B cell signaling pathway544px;text-align:justify;white-space:normal;background-color:#FFFFFF;line-height:1.
    75em;box-sizing:border-box ;overflow-wrap:break-word ;'>544px;text-align:justify;white-space:normal;background-color:#FFFFFF;line-height:1.
    75em;box-sizing:border-box ;overflow-wrap:break-word ;'>544px;text-align:justify;white-space:normal;background-color:#FFFFFF;box-sizing:border-box ;overflow-wrap:break-word ;'>5px;color:#FFFFFF;background:#374AAE;">The discovery of ibrutinib5px;color:#FFFFFF;background:#374AAE;">The discovery of ibrutinib5px;color:#FFFFFF;background:#374AAE;">The discovery of ibrutinib5px;color:#FFFFFF;background:#374AAE;">The discovery of ibrutinib5px;color:#FFFFFF;background:#374AAE;">The discovery of ibrutinibThe discovery of ibrutinib544px;text-align:justify;white-space:normal;background-color:#FFFFFF;line-height:1.
    75em;box-sizing:border-box ;overflow-wrap:break-word ;'>544px;text-align:justify;white-space:normal;background-color:#FFFFFF;line-height:1.
    75em;box-sizing:border-box ;overflow-wrap:break-word ;'>Phosphorylation can only be achieved after the tyrosine residues of BTK are combined with ATP, and BTK inhibitors can competitively bind to the active site of ATP to block the B cell signaling pathway.
    However, most BTK inhibitors are not selective and have poor safety.
    How to find efficient and safe BTK inhibitors has become a research hotspot.
    Phosphorylation can only be achieved after the tyrosine residues of BTK are combined with ATP, and BTK inhibitors can competitively bind to the active site of ATP to block the B cell signaling pathway.
    However, most BTK inhibitors are not selective and have poor safety.
    How to find efficient and safe BTK inhibitors has become a research hotspot.
    544px;text-align:justify;white-space:normal;background-color:#FFFFFF;line-height:1.
    75em;box-sizing:border-box ;overflow-wrap:break-word ;'>544px;text-align:justify;white-space:normal;background-color:#FFFFFF;line-height:1.
    75em;box-sizing:border-box ;overflow-wrap:break-word ;'>At the beginning of this century, a gene sequencing company Celera creatively proposed the idea of ​​covalently irreversible BTK inhibitors and successfully synthesized a variety of active compounds, including PCI-32765 (later ibrutinib).
    The results were published in the journal ChemmedChem in 2006.
    At the beginning of this century, a gene sequencing company Celera creatively proposed the idea of ​​covalently irreversible BTK inhibitors and successfully synthesized a variety of active compounds, including PCI-32765 (later ibrutinib).
    The results were published in the journal ChemmedChem in 2006.
    544px;text-align:justify;white-space:normal;background-color:#FFFFFF;line-height:1.
    75em;box-sizing:border-box ;overflow-wrap:break-word ;'>544px;text-align:justify;white-space:normal;background-color:#FFFFFF;line-height:1.
    75em;box-sizing:border-box ;overflow-wrap:break-word ;'>The active site of ATP is highly conserved, which is one of the reasons for the poor activity of BTK inhibitors.
    After many attempts, the researchers found that the activity of electrophilic inhibitors is better.
    First, the scientists synthesized compound 1 (shown in Figure 2 below), which showed moderate activity to BTK and high selectivity to BTK and LCK.
    The active site of ATP is highly conserved, which is one of the reasons for the poor activity of BTK inhibitors.
    After many attempts, the researchers found that the activity of electrophilic inhibitors is better.
    First, the scientists synthesized compound 1 (shown in Figure 2 below), which showed moderate activity to BTK and high selectivity to BTK and LCK.
    1

    544px;white-space:normal;background-color:#FFFFFF;text-align:center;box-sizing:border-box ;'>

    544px;white-space:normal;background-color:#FFFFFF;line-height:1.


    75em;text-align:center;box-sizing:border-box ;overflow-wrap:break-word ;'>Figure 2.
    The chemical structure of compound 1Figure 2.
    Compound 1 the chemical structure of 1544px;text-align:justify;white-space:normal;background-color:#FFFFFF;line-height:1.
    75em;box-sizing:border-box ;overflow-wrap:break-word ;'>544px;text-align:justify;white-space:normal;background-color:#FFFFFF;line-height:1.
    75em;box-sizing:border-box ;overflow-wrap:break-word ;'>The researchers continued to synthesize analogs of 1 , replacing the five-membered ring of the R group with a six-membered ring, and the activity of the product was significantly increased.
    After testing, compound 4 , that is, ibrutinib (Figure 3), has the best indicators.
    The compound binds to BTK in the form of covalent bonds.
    The structure of compound 4 contains a special Michael receptor that can interact with Hemisulfa-481 (Cys481) near the ATP catalytic center of BTK is covalently bound to irreversibly inhibit the activity of BTK (Figure 4).
    The activity of the compound has been well verified on animal models of rheumatoid arthritis.
    The researchers continued to synthesize analogs of 1 , replacing the five-membered ring of the R group with a six-membered ring, and the activity of the product was significantly increased.
    After testing, compound 4 , that is, ibrutinib (Figure 3), has the best indicators.
    The compound binds to BTK in the form of covalent bonds.
    The structure of compound 4 contains a special Michael receptor that can interact with Hemisulfa-481 (Cys481) near the ATP catalytic center of BTK is covalently bound to irreversibly inhibit the activity of BTK (Figure 4).
    The activity of the compound has been well verified on animal models of rheumatoid arthritis.


    544px;white-space:normal;background-color:#FFFFFF;line-height:1.
    75em;text-align:center;box-sizing:border-box ;'> Figure 3 The chemical structure of ibrutinib

    Figure 3 The chemical structure of ibrutinib

    544px;white-space:normal;background-color:#FFFFFF;text-align:center;box-sizing:border-box ;'>

    544px;white-space:normal;background-color:#FFFFFF;line-height:1.
    75em;text-align:center;box-sizing:border-box ;overflow-wrap:break-word ;'>Figure 4 Schematic diagram of the binding of ibrutinib to the active site Cys481 of BTKFigure 4 Schematic diagram of the binding of ibrutinib to the active site Cys481 of BTK544px;text-align:justify;white-space:normal;background-color:#FFFFFF;line-height:1.
    75em;box-sizing:border-box ;overflow-wrap:break-word ;'>544px;text-align:justify;white-space:normal;background-color:#FFFFFF;line-height:1.


    75em;box-sizing:border-box ;overflow-wrap:break-word ;'>544px;text-align:justify;white-space:normal;background-color:#FFFFFF;box-sizing:border-box ;overflow-wrap:break-word ;'>5px;color:#FFFFFF;background:#374AAE;">The difficult road to market for ibrutinib5px;color:#FFFFFF;background:#374AAE;">The difficult road to market for ibrutinib5px;color:#FFFFFF;background:#374AAE;">The difficult road to market for ibrutinib5px;color:#FFFFFF;background:#374AAE;">The difficult road to market for ibrutinib5px;color:#FFFFFF;background:#374AAE;">The difficult road to market for ibrutinibThe difficult road to market for ibrutinib544px;text-align:justify;white-space:normal;background-color:#FFFFFF;line-height:1.
    75em;box-sizing:border-box ;overflow-wrap:break-word ;'>544px;text-align:justify;white-space:normal;background-color:#FFFFFF;line-height:1.
    75em;box-sizing:border-box ;overflow-wrap:break-word ;'>Celera is a gene sequencing company.
    Due to financial and corporate strategic issues, Celera transformed into diagnostic reagents and sold new drug R&D projects to the outside world.
    It was Pharmacyclics that changed the fate of Ibrutinib.
    Pharmacyclics is a new drug innovation company, but it struggles with life and death without an excellent drug pipeline.
    At that time, the company's CEO Dr.
    Richard Miller discovered Celera's new drug project, and his eyes were bright and he bought all the compounds under the project.
    Although Celera’s scientists confirmed that PCI-32765 (ibrutinib) has excellent effects on autoimmune diseases, Miller, as an entrepreneur and oncologist, has a unique vision for the development of new anti-tumor drugs.
    He is convinced that ibrutinib It has potential value in the treatment of hematological diseases and lymphoma, and insists on in-depth research on the drug.
    Celera is a gene sequencing company.
    Due to financial and corporate strategic issues, Celera transformed into diagnostic reagents and sold new drug R&D projects to the outside world.
    It was Pharmacyclics that changed the fate of Ibrutinib.
    Pharmacyclics is a new drug innovation company, but it struggles with life and death without an excellent drug pipeline.
    At that time, the company's CEO Dr.
    Richard Miller discovered Celera's new drug project, and his eyes were bright and he bought all the compounds under the project.
    Although Celera’s scientists confirmed that PCI-32765 (ibrutinib) has excellent effects on autoimmune diseases, Miller, as an entrepreneur and oncologist, has a unique vision for the development of new anti-tumor drugs.
    He is convinced that ibrutinib It has potential value in the treatment of hematological diseases and lymphoma, and insists on in-depth research on the drug.
    544px;text-align:justify;white-space:normal;background-color:#FFFFFF;line-height:1.
    75em;box-sizing:border-box ;overflow-wrap:break-word ;'>544px;text-align:justify;white-space:normal;background-color:#FFFFFF;line-height:1.
    75em;box-sizing:border-box ;overflow-wrap:break-word ;'>However, suitable animal models are not easy to obtain.
    In the end, scientists conducted drug tests on dogs with lymphoma, and obtained ideal experimental results, but the results were not impressive.
    At this time, scientists are a bit entangled.
    For drug innovation companies, it will take great risks to continue.
    If the project fails, they will be waiting for them and the company may go bankrupt.
    Miller firmly believes that the effect of drugs can only be known through clinical trials, and he has rejected all opinions and started clinical trials.
    However, suitable animal models are not easy to obtain.
    In the end, scientists conducted drug tests on dogs with lymphoma, and obtained ideal experimental results, but the results were not impressive.
    At this time, scientists are a bit entangled.
    For drug innovation companies, it will take great risks to continue.
    If the project fails, they will be waiting for them and the company may go bankrupt.
    Miller firmly believes that the effect of drugs can only be known through clinical trials, and he has rejected all opinions and started clinical trials.
    544px;text-align:justify;white-space:normal;background-color:#FFFFFF;line-height:1.
    75em;box-sizing:border-box ;overflow-wrap:break-word ;'>544px;text-align:justify;white-space:normal;background-color:#FFFFFF;line-height:1.
    75em;box-sizing:border-box ;overflow-wrap:break-word ;'>However, clinical trials are progressing slowly, and drug development needs to continue to burn money.
    The available balance on the company's accounts is no longer large, and the company is on the verge of bankruptcy.
    At this time, Robert Duggan, chairman of the board of directors, became increasingly dissatisfied with Miller.
    He joined other investors to squeeze out Miller and become the company's new CEO.
    After Miller left, in April 2009, after the company announced the Ibrutinib clinical trial data at the American Association for Cancer Research (AACR), investors began to regain confidence in the company.
    However, clinical trials are progressing slowly, and drug development needs to continue to burn money.
    The available balance on the company's accounts is no longer large, and the company is on the verge of bankruptcy.
    At this time, Robert Duggan, chairman of the board of directors, became increasingly dissatisfied with Miller.
    He joined other investors to squeeze out Miller and become the company's new CEO.
    After Miller left, in April 2009, after the company announced the Ibrutinib clinical trial data at the American Association for Cancer Research (AACR), investors began to regain confidence in the company.
    544px;text-align:justify;white-space:normal;background-color:#FFFFFF;line-height:1.
    75em;box-sizing:border-box ;overflow-wrap:break-word ;'>544px;text-align:justify;white-space:normal;background-color:#FFFFFF;line-height:1.
    75em;box-sizing:border-box ;overflow-wrap:break-word ;'>In August 2009, Pharmacyclics signed a cooperation project with the National Institutes of Health (NIH).
    Other investors continued to invest in the company.
    Pharmacyclics has sufficient funds to continue the clinical trial process.
    In the phase II clinical trial of patients with relapsed and refractory mantle cell lymphoma (MCL), the overall patient response rate (ORR) was 68% (complete response 21%, partial response 47%), and the average progression-free survival was 13.
    9 The survival rate of 18 months and 58% is 58%.
    The emergence of ibrutinib is considered to be the most important breakthrough in the treatment of MCL so far.
    In phase III clinical trials, patients with chronic lymphocytic leukemia and small lymphocytic lymphoma were selected to compare the efficacy gap between imbruvica and ofatumumab.
    The OS (overall survival rate) and ORR of the ibrutinib group were significantly higher than those of the ofatumumab group, the OS of the ibrutinib group reached 90% (ofatumumab group was 81%), and the ibrutinib group The ORR was 43% (4% in the ofatumumab group).
    Currently, Ibrutinib has been included in the CLL treatment guidelines by NCCN in the United States.
    In August 2009, Pharmacyclics signed a cooperation project with the National Institutes of Health (NIH).
    Other investors continued to invest in the company.
    Pharmacyclics has sufficient funds to continue the clinical trial process.
    In the phase II clinical trial of patients with relapsed and refractory mantle cell lymphoma (MCL), the overall patient response rate (ORR) was 68% (complete response 21%, partial response 47%), and the average progression-free survival was 13.
    9 The survival rate of 18 months and 58% is 58%.
    The emergence of ibrutinib is considered to be the most important breakthrough in the treatment of MCL so far.
    In phase III clinical trials, patients with chronic lymphocytic leukemia and small lymphocytic lymphoma were selected to compare the efficacy gap between imbruvica and ofatumumab.
    The OS (overall survival rate) and ORR of the ibrutinib group were significantly higher than those of the ofatumumab group, the OS of the ibrutinib group reached 90% (ofatumumab group was 81%), and the ibrutinib group The ORR was 43% (4% in the ofatumumab group).
    Currently, Ibrutinib has been included in the CLL treatment guidelines by NCCN in the United States.
    544px;text-align:justify;white-space:normal;background-color:#FFFFFF;line-height:1.
    75em;box-sizing:border-box ;overflow-wrap:break-word ;'>544px;text-align:justify;white-space:normal;background-color:#FFFFFF;line-height:1.
    75em;box-sizing:border-box ;overflow-wrap:break-word ;'>After phase III clinical trials, in 2013, Ibrutinib was approved by the US FDA for marketing, becoming the only drug that has been designated by the FDA for three breakthrough treatments for the treatment of mantle cell lymphoma, Waldenstrom's macroglobulinemia and chromosome 17p Absent chronic lymphocytic leukemia.
    After phase III clinical trials, in 2013, Ibrutinib was approved by the US FDA for marketing, becoming the only drug that has been designated by the FDA for three breakthrough treatments for the treatment of mantle cell lymphoma, Waldenstrom's macroglobulinemia and chromosome 17p Absent chronic lymphocytic leukemia.
    544px;text-align:justify;white-space:normal;background-color:#FFFFFF;line-height:1.
    75em;box-sizing:border-box ;overflow-wrap:break-word ;'>544px;text-align:justify;white-space:normal;background-color:#FFFFFF;line-height:1.
    75em;box-sizing:border-box ;overflow-wrap:break-word ;'>544px;text-align:justify;white-space:normal;background-color:#FFFFFF;box-sizing:border-box ;overflow-wrap:break-word ;'>5px;color:#FFFFFF;background:#374AAE;">Final winner5px;color:#FFFFFF;background:#374AAE;">Final winner5px;color:#FFFFFF;background:#374AAE;">Final winner5px;color:#FFFFFF;background:#374AAE;">Final winner5px;color:#FFFFFF;background:#374AAE;">Final winnerFinal winner544px;text-align:justify;white-space:normal;background-color:#FFFFFF;line-height:1.
    75em;box-sizing:border-box ;overflow-wrap:break-word ;'>544px;text-align:justify;white-space:normal;background-color:#FFFFFF;line-height:1.
    75em;box-sizing:border-box ;overflow-wrap:break-word ;'>Ibrutinib was synthesized by Chinese scientists from Celera, who creatively proposed an irreversible inhibitor treatment strategy.
    However, due to the change of strategic goals, it was transferred to Pharmacyclics.
    Miller chose Ibrutinib for the treatment of CLL with his unique vision.
    It is a pity that he failed to lead Pharmacyclics out of the predicament, nor did he feel the joy of the ultimate success.
    As Miller's successor, Duggan is an excellent investor with firm belief and composure.
    He has continuously absorbed shares and has invested more than 43 million U.
    S.
    dollars.
    He has become the largest shareholder holding 20% ​​of the shares.
    In 2011, Johnson & Johnson reached an agreement with Pharmacyclics.
    Johnson & Johnson supported the research and development of Pharmacyclics' new drug ibrutinib and paid a down payment of 150 million US dollars.
    In addition, there are still 60% of the research and development expenses and nearly 1 billion.
    Milestone transfers in US dollars and more than 10% sales commission.
    In return, Johnson & Johnson has the exclusive distribution rights of Ibrutinib in the global blood disease market, becoming the biggest winner.
    In 2015, AbbVie (AbbVie) acquired Pharmacyclics for US$21 billion and, together with Johnson & Johnson, continues its research on Ibrutinib.

    Ibrutinib was synthesized by Chinese scientists from Celera, who creatively proposed an irreversible inhibitor treatment strategy.
    However, due to the change of strategic goals, it was transferred to Pharmacyclics.
    Miller chose Ibrutinib for the treatment of CLL with his unique vision.
    It is a pity that he failed to lead Pharmacyclics out of the predicament, nor did he feel the joy of the ultimate success.
    As Miller's successor, Duggan is an excellent investor with firm belief and composure.
    He has continuously absorbed shares and has invested more than 43 million U.
    S.
    dollars.
    He has become the largest shareholder holding 20% ​​of the shares.
    In 2011, Johnson & Johnson reached an agreement with Pharmacyclics.
    Johnson & Johnson supported the research and development of Pharmacyclics' new drug ibrutinib and paid a down payment of 150 million US dollars.
    In addition, there are still 60% of the research and development expenses and nearly 1 billion.
    Milestone transfers in US dollars and more than 10% sales commission.
    In return, Johnson & Johnson has the exclusive distribution rights of Ibrutinib in the global blood disease market, becoming the biggest winner.
    In 2015, AbbVie (AbbVie) acquired Pharmacyclics for US$21 billion and, together with Johnson & Johnson, continues its research on Ibrutinib. 544px;text-align:justify;white-space:normal;background-color:#FFFFFF;line-height:1.
    75em;box-sizing:border-box ;overflow-wrap:break-word ;'>544px;text-align:justify;white-space:normal;background-color:#FFFFFF;line-height:1.
    75em;box-sizing:border-box ;overflow-wrap:break-word ;'>The R&D and listing of Ibrutinib has gone through many twists and turns, such as transfer, shortage of funds, and a midway change of coaching.
    But it is fortunate.
    Miller’s wise eyes and beads, first bought out the patent right of Ibrutinib and used it for The treatment of CLL is against the crowd, and it is difficult to start clinical trials; Duggan is the continuation of Ibrutinib, and he leads the team to complete the clinical trials, so that people can see the excellent efficacy of Ibrutinib; and Big Pharma The company Johnson & Johnson bought out the right to sell Ibrutinib, enabling more people to use innovative drugs.
    The R&D and listing of Ibrutinib has gone through many twists and turns, such as transfer, shortage of funds, and a midway change of coaching.
    But it is fortunate.
    Miller’s wise eyes and beads, first bought out the patent right of Ibrutinib and used it for The treatment of CLL is against the crowd, and it is difficult to start clinical trials; Duggan is the continuation of Ibrutinib, and he leads the team to complete the clinical trials, so that people can see the excellent efficacy of Ibrutinib; and Big Pharma The company Johnson & Johnson bought out the right to sell Ibrutinib, enabling more people to use innovative drugs.
    This article is an English version of an article which is originally in the Chinese language on echemi.com and is provided for information purposes only. This website makes no representation or warranty of any kind, either expressed or implied, as to the accuracy, completeness ownership or reliability of the article or any translations thereof. If you have any concerns or complaints relating to the article, please send an email, providing a detailed description of the concern or complaint, to service@echemi.com. A staff member will contact you within 5 working days. Once verified, infringing content will be removed immediately.

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