36745-93-4

Usage

Uses

Used in Pharmaceutical Industry:
2,4-Dichloro-6-methyl-5-pyrimidinecarboxylic acid methyl ester is used as a synthetic intermediate for the preparation of 4,6,7-trisubstituted 1,2-dihydropyrrol[3,4-c]pyridin/pyrimidin-3-one derivatives. These derivatives are valuable as Btk kinase inhibitors, which play a crucial role in the treatment of various diseases, including autoimmune and inflammatory disorders, as well as certain types of cancer.
2,4-Dichloro-6-methyl-5-pyrimidinecarboxylic acid methyl ester's unique structure allows for the development of targeted therapies that can potentially minimize side effects and improve patient outcomes. By inhibiting Btk kinase, these derivatives can modulate cellular signaling pathways involved in the pathogenesis of the aforementioned conditions, offering a promising avenue for therapeutic intervention.

InChI:InChI=1S/C7H6Cl2N2O2/c1-3-4(6(12)13-2)5(8)11-7(9)10-3/h1-2H3

Upstream product

• 936020-16-5 3-amino-2-(ethoxycarbonyl-carbamoyl)-but-2-enoic acid methyl ester 
• 14205-39-1 methyl 3-aminocrotonate 
• 869891-41-8 4-methyl-2,6-dioxo-3H-pyrimidine-5-carboxylic acid methyl ester 

Downstream Products

• 1312690-45-1 methyl 2-chloro-4-methyl-6-(m-tolylamino)pyrimidine-5-carboxylate 
• 1312690-46-2 2-((1R,2S)-2-aminocyclohexylamino)-4-(m-tolylamino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-5-one 
• 1312690-47-3 methyl 2-((1R,2S)-2-(tert-butoxycarbonylamino)cyclohexylamino)-4-methyl-6-(m-tolylamino)pyrimidine-5-carboxylate 
• 1312690-48-4 tert-butyl (1S,2R)-2-(6-(2,4-dimethoxybenzyl)-5-oxo-4-(m-tolylamino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-ylamino)cyclohexylcarbamate 
• 1312691-71-6 methyl 4-methyl-2-(methylthio)-6-(m-tolylamino)pyrimidine-5-carboxylate 
• 1312691-72-7 6-(2,4-Dimethoxybenzyl)-2-(methylthio)-4-(m-tolylamino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-5-one 
• 1312691-73-8 6-(2,4-dimethoxybenzyl)-2-(methylsulfonyl)-4-(m-tolylamino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-5-one 
• 1312691-74-9 tert-Butyl 2-(6-(2,4-dimethoxybenzyl)-5-oxo-4-(m-tolylamino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-ylamino)ethylcarbamate 
• 1312690-90-6 Methyl 2-((1R,2S)-2-(tert-butoxycarbonylamino)cyclohexylamino)-4-methyl-6-(1-methyl-1H-pyrazol-4-yl)pyrimidine-5-carboxylate 
• 1312690-91-7 Methyl 2-((1R,2S)-2-(tert-butoxycarbonylamino)cyclohexylamino)-4-formyl-6-(1-methyl-1H-pyrazol-4-yl)pyrimidine-5-carboxylate 
• 1312690-92-8 tert-Butyl (1S,2R)-2-(6-(2,4-dimethoxybenzyl)-4-(1-methyl-1H-pyrazol-4-yl)-5-oxo-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-ylamino)cyclohexylcarbamate 
• 1312691-97-6 Methyl 2-(3-(tert-butoxycarbonylamino)prop-1-ynyl)-4-methyl-6-(m-tolylamino)pyrimidine-5-carboxylate 
• 1312691-98-7 methyl 2-(3-(tert-butoxycarbonylamino)propyl)-4-methyl-6-(m-tolylamino)pyrimidine-5-carboxylate 
• 1312691-99-8 tert-butyl 3-(6-(2,4-dimethoxybenzyl)-5-oxo-4-(m-tolylamino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)propylcarbamate 

Relevant academic research and scientific papers

Discovery of TAK-659 an orally available investigational inhibitor of Spleen Tyrosine Kinase (SYK)

Spleen Tyrosine Kinase (SYK) is a non-receptor cytoplasmic tyrosine kinase that is primarily expressed in hematopoietic cells. SYK is a key mediator for a variety of inflammatory cells, including B cells, mast cells, macrophages and neutrophils and therefore, an attractive approach for treatment of both inflammatory diseases and oncology indications. Using in house co-crystal structure information, and structure-based drug design, we designed and optimized a novel series of heteroaromatic pyrrolidinone SYK inhibitors resulting in the selection of the development candidate TAK-659. TAK-659 is currently undergoing Phase I clinical trials for advanced solid tumor and lymphoma malignancies, a Phase Ib study in advanced solid tumors in combination with nivolumab, and PhIb/II trials for relapsed/refractory AML.

TYK2 INHIBITORS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same for the inhibition of TYK2, and the treatment of TYK2-mediated disorders.

SUBSTITUTED AMINO-ACRYLCARBOXAMIDES AS KCNQ2/3 MODULATORS

The invention relates to amino-arylcarboxamides, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.

SUBSTITUTED AMINO-ARYLCARBOXAMIDES AS KCNQ2/3 MODULATORS

The invention relates to amino-arylcarboxamides of formula (I), to pharmaceutical compositions containing these compounds and also to these compounds for use In the treatment and/or prophylaxis of pain and further diseases and/or disorders.

FUSED HETEROAROMATIC PYRROLIDINONES

Disclosed are compounds of Formula 1, and pharmaceutically acceptable salts thereof, wherein G, L1, L2, R1, R2, R3, and R4 are defined in the specification. This disclosure also relates to materials and methods for preparing compounds of Formula 1, pharmaceutical compositions containing them, and their use for treating disorders, diseases, and conditions involving the immune system and inflammation, including rheumatoid arthritis, hematological malignancies, epithelial cancers (i.e., carcinomas), and other disorders, diseases, and conditions for which inhibition of SYK is indicated.

NITROGENATED FUSED RING DERIVATIVE, PHARMACEUTICAL COMPOSITION COMPRISING THE SAME, AND USE OF THE SAME FOR MEDICAL PURPOSES

[Purpose] The present invention provides compounds useful as agents for the prevention or treatment of a sex hormone-dependent disease or the like. [Solution] The present invention provides nitrogen-containing fused ring derivatives represented by the following general formula (I) which has a GnRH antagonistic activity, prodrugs, salts, pharmaceutical compositions containing the same, medicinal uses thereof and the like. In the formula (I), rings A and B are independently aryl or heteroaryl; RA and RB are independently halogen, cyano, alkyl, alkylsulfonyl, -OW1, -SW1, -COW2, -NW3W4, -SO2NW3W4, aryl, etc.; RC is H or alkyl; E is oxygen atom, etc.; U is single bond or alkylene; and X is Y, -CO-Y, -SO2-Y -S-(alkylene)-Y, -O-(alkylene)-Y, -SO2-(alkylene)-Y, etc.; Y is Z or amino, etc.; and Z is cycloalkyl, heterocycloalkyl, aryl, heteroaryl, etc.

4,5-DISUBSTITUTED-2-ARYL PYRIMIDINES

4,5-disubstituted-2-arylpyrimidines of Formula (I) and Formula (II) are provided: wherein R1, R2, R3, R8, R9, A and Ar are defined herein. Such compounds are ligands of C5a receptors. Preferred compounds of Formula I and II bind to C5a receptors with high affinity and exhibit neutral antagonist or inverse activity at C5a receptors. The present invention also relates to pharmaceutical compositions comprising such compounds, and to the use of such compounds in treating a variety of inflammatory, cardiovascular, and immune system disorders. In addition, the present invention provides labeled 4,5-disubstituted-2-arylpyrimidines, which are useful as probes for the localization of C5a receptors.