552295-08-6

Usage

Uses

Used in Pharmaceutical Research and Development:
4-Chloro-6-iodo-thieno[2,3-d]pyrimidine is used as a building block for the synthesis of various biologically active molecules, particularly in the field of medicinal chemistry. Its unique molecular structure allows for the preparation of new drugs and drug candidates.
Used in Agrochemical Development:
4-Chloro-6-iodo-thieno[2,3-d]pyrimidine has potential applications in the development of agrochemicals, where its molecular structure can contribute to the creation of new compounds for agricultural use.
Used in Materials Science:
In materials science, 4-chloro-6-iodo-thieno[2,3-d]pyrimidine can be utilized in the development of new materials, taking advantage of its unique molecular structure to create innovative products with specific properties.

Upstream product

• 4651-82-5 2-amino-3-cyanothiophene 
• 14080-50-3 thieno[2,3-d]pyrimidin-4(3H)one 
• 14080-59-2 4-chlorothieno[2,3-d]pyrimidine 

Relevant academic research and scientific papers

Discovery of S64315, a Potent and Selective Mcl-1 Inhibitor

Myeloid cell leukemia 1 (Mcl-1) has emerged as an attractive target for cancer therapy. It is an antiapoptotic member of the Bcl-2 family of proteins, whose upregulation in human cancers is associated with high tumor grade, poor survival, and resistance to chemotherapy. Here we report the discovery of our clinical candidate S64315, a selective small molecule inhibitor of Mcl-1. Starting from a fragment derived lead compound, we have conducted structure guided optimization that has led to a significant (3 log) improvement of target affinity as well as cellular potency. The presence of hindered rotation along a biaryl axis has conferred high selectivity to the compounds against other members of the Bcl-2 family. During optimization, we have also established predictive PD markers of Mcl-1 inhibition and achieved both efficient in vitro cell killing and tumor regression in Mcl-1 dependent cancer models. The preclinical candidate has drug-like properties that have enabled its development and entry into clinical trials.

MACROCYCLIC MCL-1 INHIBITORS AND METHODS OF USE

The present disclosure provides for compounds of Formula (I) wherein A2, A3, A4, A6, A7, A8, A15, RA, R5, R9, R10A, R10B, R11, R12, R13, R14, R16, W, X, and Y have any of the values defined in the specification, and pharmaceutically acceptable salts thereof, that are useful as agents in the treatment of diseases and conditions, including cancer. Also provided are pharmaceutical compositions comprising compounds of Formula (I).

Macrocyclic MCL-1 inhibitors and methods of use

The present disclosure provides for compounds of Formula (I) wherein A2, A3, A4, A6, A7, A8, A15, RA, R5, R9, R10A, R10B, R11, R12, R13, R14, R16, W, X, and Y have any of the values defined in the specification, and pharmaceutically acceptable salts thereof, that are useful as agents for the treatment of diseases and conditions, including cancer. Also provided are pharmaceutical compositions comprising compounds of Formula (I).

MACROCYCLIC MCL-1 INHIBITORS AND METHODS OF USE

The present disclosure provides for compounds of formula (I), wherein A2, A3, A4, A6, A7, A8, A15, RA, R5, R9, R10A, R10B, R11, R12, R13, R14, R16, W, X, and Y have any of the values defined in the specification, and pharmaceutically acceptable salts thereof, that are useful as agents in the treatment of diseases and conditions, including cancer. Also provided are pharmaceutical compositions comprising compounds of formula (I).

Structure-guided discovery of a selective mcl-1 inhibitor with cellular activity

Myeloid cell leukemia 1 (Mcl-1), an antiapoptotic member of the Bcl-2 family of proteins, whose upregulation when observed in human cancers is associated with high tumor grade, poor survival, and resistance to chemotherapy, has emerged as an attractive target for cancer therapy. Here, we report the discovery of selective small molecule inhibitors of Mcl-1 that inhibit cellular activity. Fragment screening identified thienopyrimidine amino acids as promising but nonselective hits that were optimized using nuclear magnetic resonance and X-ray-derived structural information. The introduction of hindered rotation along a biaryl axis has conferred high selectivity to the compounds, and cellular activity was brought on scale by offsetting the negative charge of the anchoring carboxylate group. The obtained compounds described here exhibit nanomolar binding affinity and mechanism-based cellular efficacy, caspase induction, and growth inhibition. These early research efforts illustrate drug discovery optimization from thienopyrimidine hits to a lead compound, the chemical series leading to the identification of our more advanced compounds S63845 and S64315.

Method for preparing multi-target small-molecule compounds S63845

The invention discloses a method for preparing multi-target small-molecule compounds S63845, and relates to the technical field of chemical synthesis. The method has the advantages that routes for synthesizing the multi-target small-molecule compounds S63

NEW AMMONIUM DERIVATIVES, A PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM

Compounds of formula (I): wherein R1, R2, R3, R4, R5, R6 and Y are as defined in the description. Medicaments.

NEW HYDROXYESTER DERIVATIVES, A PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM

Compounds of formula (1) wherein R1, R2, R3, R4, R5, R6, R7, R13, Ra, Rb, A and n are as defined in the description. Medicaments containing them

NEW AMINOACID DERIVATIVES, A PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM

Compounds of formula (I): wherein R1, R2, R5, R6, R7, R12, X, Y, A, E and n are as defined in the description. Medicaments.

NEW HYDROXYACID DERIVATIVES, A PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM

Compounds of formula (I): wherein R1, R2, R3, R4, R5, R6, R7, R8, R14, A and n are as defined in the description. Medicaments.