The introduction and synthesis route of small molecule kinase inhibitors approved by FDA in 2017

A total of seven new small molecule kinase inhibitors have been approved by FDA in 2017. Protein kinases form a very large family of signaling proteins, with more than 500 encoded in the human genome. They have many diverse roles in cells and can be regulated in a variety of ways providing essential nodes in intracellular signaling pathways that act to define and/or integrate intracellular communication. A protein kinase is a kinase enzyme that modifies other proteins by chemically adding phosphate groups to them (phosphorylation). Phosphorylation usually results in a functional change of the target protein (substrate) by changing enzyme activity, cellular location, or association with other proteins.

Protein kinases fall into two major categories, serine/threonine-specific protein kinases and tyrosine-specific protein kinases. Many researches proved that the protein kinases are the ideal drug targets.

Below is the brief information of the small molecule kinase inhibitors approved by FDA in 2017

small molecule kinase inhibitors approved by FDA in 2017

1. Acalabrutinib

On October 31, 2017, the FDA granted accelerated approval to acalabrutinib for treatment of adult patients with mantle cell lymphoma (MCL) who have received at least one prior therapy. B-cell receptor (BCR) signalling is central to the survival and proliferation of malignant B cells, and Bruton tyrosine kinase (BTK), an integral member of the BCR pathway, is a clinically validated target in mantle cell lymphoma.

Acalabrutinib (ACP-196) is a highly selective, potent BTK inhibitor developed to minimise off-target activity. Findings from in-vitro studies showed that acalabrutinib has more selective BTK inhibition and higher in-vivo potency than ibrutinib. The phase 1/2 ACE-CL-001 trial of acalabrutinib monotherapy in patients with relapsed chronic lymphocytic leukaemia showed that acalabrutinib has rapid oral absorption and a short plasma half-life.

The synthesis route of acalabrutinib

2. Neratinib

On July 17, 2017, the FDA approved Nerlynx (neratinib) for the extended adjuvant treatment of early-stage, HER2-positive breast cancer. Neratinib is a kinase inhibitor that irreversibly binds to epidermal growth factor receptor (EGFR), human epidermal growth factor receptor 2 (HER2), and HER4. In vitro, neratinib inhibited cell proliferation, EGFR and HER2 autophosphorylation, downstream MAPK and AKT signaling pathways, and cell cycle regulatory pathway activities in HER2- and EGFR-dependent cancer cell lines. Neratinib human metabolites M3, M6, M7, and M11 inhibited the activity of EGFR, HER2, and HER4 in vitro. In vivo, oral administration of neratinib inhibited tumor growth in mouse xenograft models with tumor cell lines expressing HER2 and EGFR.

3. Brigatinib

On April 28, 2017, the FDA granted accelerated approval to brigatinib for the treatment of patients with metastatic anaplastic lymphoma kinase (ALK)-positive non-small cell lung cancer (NSCLC) who have progressed on or are intolerant to crizotinib. Brigatinib acts as both a anaplastic lymphoma kinase (ALK) and epidermal growth factor receptor (EGFR) inhibitor.

The synthesis route of brigatinib

4. Midostaurin

Midostaurin (CGP41251; PKC412) is a multikinase inhibitor recently approved for 2 indications in adult patients: (1) newly diagnosed acute myeloid leukemia (AML) with fms-like tyrosine kinase 3 (FLT3) mutations and (2) advanced systemic mastocytosis (SM).

The synthesis route of midostaurin

5. Ribociclib

On March 13, 2017, the FDA approved ribociclib, a cyclin-dependent kinase 4/6 inhibitor, in combination with an aromatase inhibitor as initial endocrine-based therapy for the treatment of postmenopausal women with hormone receptor (HR)-positive, human epidermal growth factor receptor 2 (HER2)-negative advanced or metastatic breast cancer.

The synthesis route of ribociclib

6. Abemaciclib

On September 28, 2017, the FDA approved abemaciclib in combination with fulvestrant for women with HR-positive, HER2-negative advanced or metastatic breast cancer with disease progression following endocrine therapy. In addition, abemaciclib was approved as monotherapy for women and men with HR-positive, HER2-negative advanced or metastatic breast cancer with disease progression following endocrine therapy and prior chemotherapy in the metastatic setting.

The synthesis route of abemaciclib

7. Copanlisib

On September 14, 2017, the FDA granted accelerated approval to copanlisib for the treatment of adult patients with relapsed follicular lymphoma who have received at least two prior systemic therapies.

The synthesis route of copanlisib

References:

1.Current Opinion in Chemical Biology 2017, 39:126-132

2.WO2013010868

3.CN102731395

4.JP2017186345

5.WO2016192522

6.WO2010075074

7.US2013261113