106261-48-7

Usage

Uses

Used in Pharmaceutical Industry:
4-(4-Methylpiperazin-1-ylmethyl)benzoic acid is used as a pharmaceutical intermediate for the development of Imatinib, a potent and selective inhibitor of certain tyrosine kinases. Imatinib is primarily used in the treatment of chronic myeloid leukemia (CML), gastrointestinal stromal tumors (GIST), and other malignancies. The compound's role as an intermediate allows for the creation of effective and targeted therapies for these conditions.
As an intermediate in the synthesis of Imatinib, 4-(4-Methylpiperazin-1-ylmethyl)benzoic acid plays a vital role in the pharmaceutical industry. Its incorporation into the drug development process enables the creation of therapies that can effectively target and inhibit specific tyrosine kinases, leading to improved treatment options for patients suffering from various types of cancer.

InChI:InChI=1/C13H18N2O2/c1-14-6-8-15(9-7-14)10-11-2-4-12(5-3-11)13(16)17/h2-5H,6-10H2,1H3,(H,16,17)

Upstream product

• 109-01-3 1-methyl-piperazine 
• 1642-81-5 p-(chloromethyl)benzoic acid 
• 619-66-9 4-Carboxybenzaldehyde 
• 2417-72-3 Methyl 4-(bromomethyl)benzoate 
• 1571-08-0 methyl 4-formylbenzoate 
• 728936-43-4 4-(4-methylpiperazin-1-ylmethyl)benzoic acid methyl ester hydrochloride 
• 314268-40-1 4-((4-methylpiperazin-1-yl)methyl)-benzoic acid methyl ester 

Downstream Products

• 314268-40-1 4-((4-methylpiperazin-1-yl)methyl)-benzoic acid methyl ester 
• 887399-39-5 4-(4-methyl-piperazin-1-ylmethyl)-N-[3-(2-oxo-2,3-dihydro-1H-indol-7-ylamino)-phenyl]-benzamide 
• 887399-45-3 4-(4-methyl-piperazin-1-ylmethyl)-N-[3-(2-oxo-2,3-dihydro-1H-indol-5-ylamino)-phenyl]-benzamide 
• 777054-54-3 methyl-phenyl-carbamic acid 4-{2-[4-(4-methyl-piperazin-1-ylmethyl)-benzoylamino]-ethyl}-phenyl ester 
• 152459-95-5 imatinib 
• 1221433-99-3 (Z)-N-[3-(3,5-dimethyl-1H-pyrrol-2-ylmethylene)-2-oxo-2,3-dihydro-1H-indol-5-yl]-4-(4-methyl-piperazin-1-ylmethyl)-benzamide 
• 1364710-26-8 (8S,9S,10R,13S,14S,17S)-10,13-dimethyl-17-((E)-1-(4-((4-methylpiperazin-1-yl)methyl)benzoyloxyimino)ethyl)-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one 
• 1382842-15-0 N-(3-(3-(cyclopropanecarboxamido)isoquinolin-7-yl)-4-methylphenyl)-4-((4-methylpiperazin-1-yl)methyl)benzamide 
• 1616628-84-2 N-(2-acetyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methyl-5-[4-(4-methylpiperazin-1-ylmethyl)-benzoylamino]-benzamide 
• 1240322-41-1 ND₀₁₁₈ 
• 1616628-87-5 5-{(2-methyl-5-[4-((4-methylpiperazin-1-yl)methyl)benzoylamino]benzyl)amino}-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid 
• 581076-60-0 N-(4-methyl-3-nitrophenyl)-4-[(4-methylpiprazin-1-yl)methyl]benzamide 
• 1616689-28-1 5-{(2-methyl-5-[4-((4-methylpiperazin-1-yl)methyl)benzoylamino]phenoxy)methyl}-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid methyl ester 
• 1616689-18-9 5-(2-{2-methyl-5-[4-(4-methylpiperazin-1-ylmethyl)-benzoylamino]-phenyl}-vinyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Discovery and Structural Optimization of 4-(Aminomethyl)benzamides as Potent Entry Inhibitors of Ebola and Marburg Virus Infections

The recent Ebola epidemics in West Africa underscore the great need for effective and practical therapies for future Ebola virus outbreaks. We have discovered a new series of remarkably potent small molecule inhibitors of Ebola virus entry. These 4-(aminomethyl)benzamide-based inhibitors are also effective against Marburg virus. Synthetic routes to these compounds allowed for the preparation of a wide variety of structures, including a conformationally restrained subset of indolines (compounds 41-50). Compounds 20, 23, 32, 33, and 35 are superior inhibitors of Ebola (Mayinga) and Marburg (Angola) infectious viruses. Representative compounds (20, 32, and 35) have shown good metabolic stability in plasma and liver microsomes (rat and human), and 32 did not inhibit CYP3A4 nor CYP2C9. These 4-(aminomethyl)benzamides are suitable for further optimization as inhibitors of filovirus entry, with the potential to be developed as therapeutic agents for the treatment and control of Ebola virus infections.

A practical synthesis of 4-[(4-methylpiperazin-1-yl)methyl]benzoic acid - The key precursor toward imatinib

A simple and efficient in situ synthesis of 4-[(4-methylpiperazin-1-yl) methyl]benzoic acid through direct reductive alkylation of 1-methylpiperazine in the presence of triacetoxy sodium borohydride in 95-99% yields is elaborated. The process is easy to scale-up for the large-scale synthesis of 4-[(4-methylpiperazin-1-yl)methyl]benzoic acid as the key synthetic intermediate of imatinib. This method was used for the synthesis of benzyl derivatives of heterocyclic amines in 87-90% yields.

Application of N-substituted (aminomethyl)benzoate strategy in design of scutellarein derivatives with improved Caco-2 cell permeability and in vitro antioxidative activity

A series of 4′-N-substituted (aminomethyl)benzoate derivatives of scutellarein were designed and synthesized. Evaluation of their physiochemical properties showed that the designed target compounds 5a-e exhibit higher chemical stability and aqueous solubility than scutellarin and scutellarein. The permeability (Papp AP to BL) of 5c-e in Caco-2 cells were 2.8, 8.1, and 12.6 times higher than that of scutellarin and 1.3, 4.1, and 6.0 times higher than that of scutellarein; especially, 5e had the highest Papp AP to BL value (7.19 ± 0.31 × 10-6 cm/s) and the lowest ER (Papp BL to AP/Papp AP to BL) value of 0.17. In vitro antioxidative evaluation results revealed that 5e could protect against H2O2-induced PC12 cells' oxidative damage by attenuating mitochondrial membrane potential loss and decreasing H2O2-induced reactive oxygen species (ROS) production.

C-3 NOVEL TRITERPENONE WITH C-17 REVERSE AMIDE DERIVATIVES AS HIV INHIBITORS

The present invention relates to C-3 novel triterpenone with C-17 reverse amide compounds of Formula (I); and pharmaceutically acceptable salts thereof, wherein ring Formula (II), R1, R2, R3, R4, R5, R6, R7, 'n' and 'm' are as defined in Formula (I). The invention also relates to C-3 novel triterpenone with C-17 reverse amide derivatives, related compounds, and pharmaceutical compositions useful for the therapeutic treatment of viral diseases and particularly HIV mediated diseases.

N-phenyl-2-pyrimidine-amine derivatives

The present invention relates to novel amides and a process for preparing these amides.

Combination of 4-anilinoquinazoline, arylurea and tertiary amine moiety to discover novel anticancer agents

In present study, 4-anilinoquinazolines scaffold, arylurea and tertiary amine moiety were combined to design, synthesize gefitinib analogs and discover novel anticancer agents. A series of 4-anilinoquinazoline derivatives (1, 2, 3 and 4) bearing arylurea and tertiary amine moiety at its 6-position were synthesized. Their antiproliferative activities in vitro were evaluated via MTT assay against A431 cell and A549 cell. The SAR of the title compounds was discussed. The compounds 2d, 2i and 2j with potent antiproliferative activities were evaluated their inhibitory activity against EGFR-TK. Compound 2j displayed potent inhibitory activity against EGFR-TK. In addition, compound 2j, at 50 mg/kg, can completely inhibit cancer growth in established nude mouse A549 xenograft model in vivo. These results suggest that the 4-anilinoquinazoline derivatives bearing diarylurea and tertiary amino moiety at its 6-position can serve as anticancer agents and EGFR inhibitors.

COMPOSITIONS AND METHODS FOR INHIBITING KINASES

The present invention provides compounds for the prevention or treatment of cancer or a bacterial or viral infection. Additionally, the present invention provides compositions and methods for using these compounds and compositions in the prevention or treatment of cancer or a bacterial or viral infection in a subject.

PROTEIN KINASE INHIBITORS

The present invention relates to compounds of the following formula (I) and/or the pharmaceutically acceptable addition salts, solvates, enantiomers, diastereoisomers thereof, as well as mixtures thereof. The subject matter of the present invention thus also includes the preparation of compounds of formula (I), their uses, in particular in the inhibition of protein kinases which are implicated for example in numerous diseases such as cancers or immune system disorders.

AZAINDOLE DERIVATIVES AS MULTI KINASE INHIBITORS

The present invention relates to compounds of the following formula (I) and/or the pharmaceutically acceptable addition salts, solvates, enantiomers, diastereoisomers thereof, as well as mixtures thereof. The subject matter of the present invention thus also includes the preparation of compounds of formula (I), their uses, in particular in the inhibition of protein kinases which are implicated for example in numerous diseases such as cancers or immune system disorders.

Preparative synthesis of heterocyclic and aromatic N-benzyl amines

A simple and highly efficient procedure has been proposed for the synthesis of heterocyclic and aromatic N-benzyl amines via reductive amination of substituted aromatic aldehydes in the presence of sodium tetrahydridoborate- acetic acid system generating reactive sodium triacetoxyhydridoborate.