2486-71-7

Usage

Uses

Used in Pharmaceutical Industry:
4-Amino-3-chlorobenzoic acid is used as a reagent for the synthesis of 1H-Pyrrolo[3,2-c]pyridine inhibitors. These inhibitors target mitotic kinase MPS1, which is overexpressed in cancer cell lines. By inhibiting MPS1, these compounds can potentially disrupt the cell division process in cancer cells, leading to their death and providing a therapeutic approach to cancer treatment.
The chemical properties of 4-Amino-3-chlorobenzoic acid, such as its reactivity and structural features, make it a valuable component in the development of new drugs and pharmaceutical compounds. Its application in the synthesis of MPS1 inhibitors highlights its potential in contributing to the fight against cancer.

InChI:InChI=1/C7H6ClNO2/c8-5-3-4(7(10)11)1-2-6(5)9/h1-3H,9H2,(H,10,11)/p-1

Upstream product

• 74114-62-8 4-acetamido-3-chlorobenzoic acid 
• 556-08-1 p-(acetylamino)benzoic acid 
• 21803-75-8 4-amino-3-chlorobenzonitrile 
• 84228-44-4 methyl 4-amino-3-chlorobenzoate 
• 82765-44-4 1-amino-2-chloro-4-carboethoxybenzene 
• 150-13-0 4-amino-benzoic acid 
• 18931-78-7 N-(2-chloro-4-methylphenyl)acetamide 

Downstream Products

• 851091-96-8 1-[2-(4-amino-3-chloro-benzoylamino)-3,3-dimethyl-butyryl]-pyrrolidine-2-carboxylic acid (2-ethoxy-5-oxo-tetrahydro-furan-3-yl)-amide 
• 74114-62-8 4-acetamido-3-chlorobenzoic acid 
• 851091-96-8 (S)-1-((S)-2-{[1-(4-amino-3-chlorophenyl)methanoyl]amino}-3,3-dimethylbutanoyl)pyrrolidine-2-carboxylic acid ((2R,3S)-2-ethoxy-5-oxo-tetrahydrofuran-3-yl)amide 
• 1145780-13-7 4-benzenesulfonylamino-3-chlorobenzoic acid 
• 374773-69-0 1-[2-(4-amino-3-chlorobenzoylamino)-3,3-dimethylbutyryl]pyrrolidine-2-carboxylic acid tert-butyl ester 
• 1343459-14-2 4-[(3-bromo-benzylidene)-amino]-3-chloro-benzoic acid methyl ester 
• 84228-44-4 methyl 4-amino-3-chlorobenzoate 
• 1019017-33-4 (4-amino-3-chlorophenyl)(pyrrolidin-1-yl)methanone 
• 1341102-55-3 2-chloro-4-(pyrrolidin-1-ylmethyl)benzenamine 
• 1390657-73-4 7-chloro-5-(2-chloro-4-(pyrrolidin-1-ylmethyl)phenylamino)pyrido[3,4-d]pyridazin-4(3H)-one 
• 1390656-13-9 5-{[2-chloro-4-(pyrrolidin-1-ylmethyl)phenyl]amino}-7-[(cyclopropylmethyl)amino]pyrido[3,4-d]pyridazin-4-ol 
• 1390656-16-2 5-{[2-chloro-4-(pyrrolidin-1-ylmethyl)phenyl]amino}-7-(4-hydroxypiperidin-1-yl)pyrido[3,4-d]pyridazin-4(3H)-one 
• 1390656-17-3 5-{[2-chloro-4-(pyrrolidin-1-ylmethyl)phenyl]amino}-7-(3-hydroxyazetidin-1-yl)pyrido[3,4-d]pyridazin-4(3H)-one 
• 1392825-60-3 C₂₁H₁₅ClN₂O₂S 

Relevant academic research and scientific papers

Highly selective oxidative monochlorination to synthesize organic intermediates: 2-Chlorotoluene, 2-chloroaniline, 2-chlorophenol, and 2-chloro-4-methylphenol

An alternative manufacturing process scheme was developed to synthesize monochloro-substituted aromatic compounds in high selectivity, involving oxidalive chlorination by using HCI-H2O2. Thus, 2-chlorotoluene, 2-chloroaniline, and 2-chlorophenol were synthesized by oxidative chlorination followed by desulphonation or decarboxylation. Oxidative chlorination of 4-methylbenzenesulphonic acid, 4-methylbenzoic acid, 4-aminobenzoic acid, and 4-hydroxybenzoic acid by using a suitable ratio of reactantr:HCI:H2O2, and their subsequent desulphonation or decarboxylation, gave 60-85% yield of the desired products. Oxidative chlorination of 4-methylphenol by using HCI-H2O2 gave as high as 98% selectivity to the desired 2-chloro-4-methylphenol.

PRO-DRUGS OF N-THIAZOL-2YL-BENZAMIDE DERIVATIVES

The invention relates to compounds of the formula I wherein the variables are as defined in the claims. The compounds are pro-drugs of A2A-receptor ligands with improved aqueous solubility, and are useful in the treatment of neurological and psychiatric disorders where an A2A-receptor is implicated.

HIV REVERSE TRANSCRIPTASE INHIBITORS

Tetrazolyl derivatives of Formula I: are HIV reverse transcriptase inhibitors, wherein U is O, S(O)n where n is an integer equal to zero, 1 or 2, or N(R4); V is optionally substituted C1-8 alkylene; W is C(O)N(R2) or a direct bond linking V to R3; and R1, R2, R3 and R4 are defined herein. The derivatives of Formula I are useful in the inhibition of HIV reverse transcriptase, the prevention and treatment of infection by HIV and in the prevention, delay in the onset, and treatment of AIDS. The derivatives are employed against HIV infection and AIDS as compounds per se or in the form of pharmaceutically acceptable salts. The derivatives and their salts can be employed as ingredients in pharmaceutical compositions, optionally in combination with other antivirals, immunomodulators, antibiotics or vaccines.

N-THIAZOL-2-YL-BENZAMIDE DERIVATIVES

The invention relates to N-thiazol-2-yl-benzamide derivatives of the formula I in the description wherein the variables are as defined in the claims. The compounds are A2A-receptor ligands, such as antagonists, agonists, reverse agonists or partial agonists, and are useful in the treatment of neurological and psychiatric disorders where an A2A-receptor is implicated.

Drug evolution concept in drug design: 1. Hybridization method

A novel concept, "drug evolution", is proposed to develop chemical libraries that have a high probability of finding drugs or drug candidates. It converts biological evolution into chemical evolution. In this paper, we present "hybridization" drug evolution, which is the equivalent of sexual recombination of parental genomes in biological evolution. The hybridization essentially shuffles the building blocks of the parent drugs and ought to drug(s); no drug evolution can otherwise occur. We hybridized two drugs, benzocaine and metoclopramide and generated 16 molecules that include the parent drugs, four known drugs, and two molecules whose therapeutic activities are reported. The unusually high number of drugs and drug candidates in the library encourages high expectations of finding new drug(s) or drug candidate(s) within the remaining eight compounds. Interestingly, the therapeutic applications of the eight drugs or drug candidates in the library are fairly diverse as 38 therapeutic applications and 25 molecular targets are counted. Therefore, the library fits as a general chemical library for unspecified therapeutic activities. The hybridization of other two drugs, aspirin and cresotamide, is also described to demonstrate the generality of the method.

Inhibitors of caspases

The present invention relates to novel classes of compounds which are caspase inhibitors, in particular interleukin-1β converting enzyme (“ICE”) inhibitors. This invention also relates to pharmaceutical compositions comprising these compounds. The compounds and pharmaceutical compositions of this invention are particularly well suited for inhibiting caspase activity and consequently, may be advantageously used as agents against interleukin-1-(“IL-1”), apoptosis-, interferon-γ inducing factor-(IGIF), or interferon-γ-(“IFN-γ”) mediated diseases, including inflammatory diseases, autoimmune diseases, destructive bone disorders, proliferative disorders, infectious diseases, and degenerative diseases. This invention also relates to methods for inhibiting caspase activity and decreasing IGIF production and IFN-γ production and methods for treating interleukin-1, apoptosis-, and interferon-γ-mediated diseases using the compounds and compositions of this invention. This invention also relates to methods of preparing the compounds of this invention.

Compositions and use of benzamides and nicotinamides as anti-inflammatory agents

The use of benzamide and nicotinamide analogs, in particular N-substituted benzamides and nicotinamides, other than benzamides with N-pyridinyl substitutions, as anti-inflammatory agents.

Synthesis and biological evaluation of novel prodrugs of anthracyclines for selective activation by the tumor-associated protease plasmin

New prodrugs of daunorubicin and doxorubicin designed for selective activation by the serine protease plasmin are described. The low toxic prodrugs 3, 4, and 5 are converted to the corresponding cytotoxic drugs upon proteolysis by the tumor-associated protease plasmin. Application of a self- eliminating spacer was essential for enzyme activation. A prodrug containing a chloro-substituted spacer was synthesized with the aim of enhancing the rate of conversion by plasmin. All prodrugs were highly stable in buffer solution and in serum and on the average 15-fold less cytotoxic than the parent drugs in seven human tumor cell lines. A marked in vitro selectivity was demonstrated by incubation of the doxorubicin prodrugs with a plasmin generating MCF-7 breast cancer cell line transfected with urokinase-type plasminogen activator (u-PA) in comparison with the nontransfected nonplasmin generating cell line. Prodrugs 4 and 5 showed the same cytotoxic effect as the free parent drug doxorubicin in the u-PA transfected cells, indicating complete conversion of the prodrug by plasmin. Addition of the plasmin inhibitor Trasylol drastically increased the ID50 values in the u-PA transfected MCF-7 cells for both prodrugs 4 and 5.

Therapeutic derivatives of diphosphonates

Novel chemotherapeutic agents having utility in treating infectious diseases such as periodontal disease, certain urinary tract infections, infectious urinary tract stones, and bone cancer, are obtained by combining chemically a diphosphonate compound with a therapeutic agent effective against the foregoing diseases.

SYNTHESIS AND STRUCTURE OF MONOCHLORO DERIVATIVES OF 2-(4-AMINOPHENYL)-5(6)-AMINOBENZIMIDAZOLE

Methods for the production of the monochloro derivatives of 2-(4-aminophenyl)-5(6)-aminobenzimidazole from chloronitrobenzanilides or by the condensation of 1,2,4-triaminobenzene with chloroaminobenzoic acid were investigated.It was established that the nitration of o-chlorobenzanilides takes place selectively in a mixture of acetic acid, acetic anhydride, and chloroform, while the nitration of 4(7)- or 5(6)-chlorobenzimidazoles takes place in sulfuric acid.The effect of the chlorine atoms and the nitro (amino) group on the IR and PMR spectra of the benzanilides and benzimidazoles is determined by their mutual position and by the position in relation of the amide bridge or the condensed imidazole ring.Analysis of the PMR spectra of the chlorodiaminophenylbenzimidazoles indicated that the amino group was localized at position 6 of the benzimidazole ring.