61694-98-2

Usage

Uses

Used in Organic Synthesis:
5-Chloro-2-methoxy-4-methylaminobenzoic Acid is used as a key intermediate in the synthesis of various organic compounds. Its unique functional groups allow for a wide range of chemical reactions, making it a versatile building block for the development of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 5-Chloro-2-methoxy-4-methylaminobenzoic Acid is used as a starting material for the synthesis of various drug candidates. Its structural features enable the creation of novel compounds with potential therapeutic applications, such as antimicrobial, anti-inflammatory, and analgesic properties.
Used in Agrochemical Industry:
5-Chloro-2-methoxy-4-methylaminobenzoic Acid is also utilized in the agrochemical industry for the development of new pesticides and herbicides. Its chemical properties allow for the design of compounds with improved efficacy and selectivity, contributing to more sustainable agricultural practices.
Used in Dye and Pigment Industry:
In the dye and pigment industry, 5-Chloro-2-methoxy-4-methylaminobenzoic Acid serves as a precursor for the synthesis of various dyes and pigments. Its ability to form stable chromophores makes it suitable for the production of colorants used in textiles, plastics, and other materials.
Used in Research and Development:
5-Chloro-2-methoxy-4-methylaminobenzoic Acid is also employed in research and development settings, where it is used to study the properties and reactivity of various functional groups. Its unique structure provides valuable insights into the design and synthesis of new organic compounds with potential applications in various industries.

Upstream product

• 78775-33-4 5-chloro-2-methoxy-4-(methylamino)benzoic acid methyl ester 
• 483303-93-1 5-chloro-2-methoxy-4-[N-methyl-N-(p-toluenesulfonyl)]aminobenzoic acid 
• 78775-31-2 4-(p-toluenesulfonyl)aminosalicylic acid 
• 476615-13-1 2-methoxy-4-[N-methyl-N-(p-toluenesulfonyl)]aminobenzoic acid 
• 78784-42-6 methyl 2-methoxy-4-(N-methyl-N-tosylamido)benzoate 
• 78775-32-3 methyl 5-chloro-2-methoxy-4-(N-methyl-N-tosylamido)benzoate 

Downstream Products

• 66898-86-0 N-(1-Benzyl-piperidin-4-yl)-5-chloro-2-methoxy-4-methylamino-benzamide 

Relevant academic research and scientific papers

THERAPEUTIC AGENT FOR RESPIRATORY DISEASE CONTAINING 4-HYDROXYPIPERIDINE DERIVATIVE AS ACTIVE INGREDIENT

An agent for preventing/treating respiratory diseases contains, as an active ingredient, a compound represented by following Formula (I): wherein A is a group represented by L-W [wherein L is a bond or CH2; and W is O, SOn (wherein n is 0 to 2), or -NR7-(wherein R7 is hydrogen or lower alkyl)]; each of G1 and G2 is (CH2)r (wherein r is 0 to 2), provided that when n is 1, G1 and G2 may be bridged by lower alkylene; Y is a lower alkylene or (substituted) benzylidene; Z is a bond or O, provided that when Z is a bond, Y may form a 5- or 6-membered ring with carbon on the benzene ring; R1 is, for example, NO2, a lower alkoxycarbonyl, (substituted) carbamoyl, (protected) hydroxyl group, (protected) carboxyl, or (protected) N-hydroxycarbamoyl; each of R2and R3 is hydrogen, halogen, (halogenated) lower alkyl, (halogenated) lower alkoxy or NO2; each of R4 and R5 is, for example, hydrogen, halogen, (halogenated) lower alkyl, (halogenated) lower alkoxy, CN, or lower alkylsulfonyl; and R6 is hydrogen or lower alkyl, a salt thereof or a solvate of them. It has excellent antitussive activity when used as an agent for preventing/treating respiratory diseases such as lung cancer, common cold syndrome, pulmonary tuberculosis, pneumonia, acute bronchitis or chronic bronchitis.

Synthesis and structure-activity relationships of 4-amino-5-chloro-N-(1,4- dialkylhexahydro-1,4-diazepin-6-yl)-2-methoxybenzamide derivatives, novel and potent serotonin 5-HT3 and dopamine D2 receptors dual antagonist

In search of a dopamine D2 and serotonin 5-HT3 receptors dual antagonist as a potential broad antiemetic agent, a number of benzamides were prepared from 4-amino-5-chloro-2-methoxybenzoic acid derivatives and 6-amino-1,4-dialkylhexahydro-1,4-diazepines and evaluated for their binding affinity for the dopamine D2 and the serotonin 5-HT3 receptors using rat brain synaptic and rat cortical membranes, respectively. From the results of both in vitro receptor binding and in vivo biological assays for the dopamine D2 receptor, 1-ethyl-4-methylhexahydro-1,4- diazepine ring was selected as an optimum amine moiety. Introduction of one methyl group on the nitrogen atom at the 4-position and/or modification of the substituent at the 5-position of the 4-amino-5-chloro-2-methoxybenzoyl moiety caused a marked increase in the dopamine D2 receptor binding affinity along with a potent 5-HT3 receptor binding affinity. Among the compounds, 5-chloro-N-(1-ethyl-4-methylhexahydro-1,4-diazepin-6-yl)-2-methoxy-4- methylaminobenzamide (82), 5-bromo (110), and 5-iodo (112) analogues exhibited a much higher affinity for the dopamine D2 receptor than that of metoclopramide (IC50=17.5-61.0 nM vs. 483 nM). In particular, 82 showed a potent antagonistic activity for both receptors in vivo tests. Optical resolution of the racemate 82 brought about a dramatic change in the pharmacological profile with the (R)-enantiomer exhibiting a strong affinity for both the dopamine D2 and the 5-HT3 receptors, while the corresponding (S)-enantiomer had a potent and selective serotonin 5-HT 3 receptor binding affinity.