857070-66-7

Usage

Uses

Used in Pharmaceutical Industry:
2-Chloro-1H-benzimidazole-6-methanol is used as a key intermediate in the development of anti-cancer drugs, where its unique structure contributes to the creation of novel therapeutic agents. It is valued for its potential to be incorporated into compounds that target various types of cancer, offering new avenues for treatment.
Used in Antiviral Medications:
In the field of antiviral research, 2-CHLORO-1H-BENZIMIDAZOLE-6-METHANOL is utilized as a precursor for the synthesis of antiviral medications. Its chemical properties allow for the design of compounds that can inhibit viral replication and reduce the severity of viral infections.
Used in Agrochemical Products:
2-Chloro-1H-benzimidazole-6-methanol is also used as a building block in the development of crop protection products within the agrochemical industry. Its versatility in organic chemistry enables the synthesis of compounds that can protect crops from pests and diseases, thereby enhancing agricultural productivity.
Used in Organic Chemistry Research:
As a valuable tool in organic chemistry, 2-CHLORO-1H-BENZIMIDAZOLE-6-METHANOL is used in research to explore new chemical compounds and reactions. Its presence of functional groups makes it an ideal candidate for studying various organic transformations and the development of innovative synthetic pathways.

Upstream product

• 857035-29-1 2-chloro-3H-benzoimidazole-5-carboxylic acid ethyl ester 
• 634602-84-9 2-hydroxy-3H-benzoimidazole-5-carboxylic acid ethyl ester 
• 37466-90-3 ethyl 3,4-diaminobenzoate 

Downstream Products

• 857070-65-6 3-(3-hydroxy-6-methylpyridin-2-ylmethyl)-2-(3-morpholin-4-ylpropylamino)-3H-benzoimidazole-5-carbaldehyde 
• 857067-39-1 2-[5-hydroxymethyl-2-(3-morpholin-4-ylpropylamino)benzoimidazol-1-ylmethyl]-6-methylpyridin-3-ol 
• 857067-38-0 2-[6-hydroxymethyl-2-(3-morpholin-4-ylpropylamino)benzoimidazol-1-ylmethyl]-6-methylpyridin-3-ol 
• 857070-67-8 [2-(3-morpholin-4-ylpropylamino)-3H-benzoimidazol-5-yl]methanol 

Relevant academic research and scientific papers

Selection of a respiratory syncytial virus fusion inhibitor clinical candidate. 2. Discovery of a morpholinopropylaminobenzimidazole derivative (TMC353121)

A preceding paper (Bonfanti et al. J. Med Chem. 2007, 50, 4572-4584) reported the optimization of the pharmacokinetic profile of substituted benzimidazoles by reducing their tissue retention. However, the modifications that were necessary to achieve this goal also led to a significant drop in anti-RSV activity. This paper describes a molecular modeling study followed by a lead optimization program that led to the recovery of the initial potent antiviral activity and the selection of TMC353121 as a clinical candidate.

HETEROCYCLYLAMINOALKYL SUBSTITUTED BENZIMIDAZOLES

Heterocyclylaminoalkyl Substituted Benzimidazoles Inhibitors of RSV replication of formula (I): The salts and stereochemically isomeric forms thereof, wherein Q is hydrogen, C1-6alkyl optionally substituted with a heterocycle or Q is C1 -6alkyl substituted with both -OR4 and a heterocycle; wherein said heterocycle is oxazolidine, thiazolidine, 1-oxo-thiazolidine, 1,1-dioxothiazolidine, morpholinyl, thiomorpholinyl, 1-oxo-thiomorpholinyl, 1,1-dioxothiomorpholinyl, hexahydrooxazepine, hexahydrothiazepine, 1-oxo-hexahydrothiazepine, 1,1-dioxo-hexahydrothiazepine, pyrrolidine, piperidine, homopiperidine, piperazine; which heterocyle may be substituted with 1-2 substituents; each Alk is C1 -6alkanediyl; R1 is Ar or optionally substituted piperidinyl, piperazinyl, morpholinyl, thiomorpholinyl, pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl, furanyl, tetrahydrofuranyl, thienyl, pyrrolyl, thiazolyl, oxazolyl, imidazolyl, isothiazolyl, pyrazolyl, isoxazo lyl, oxadiazolyl, quinolinyl, quinoxalinyl, benzofuranyl, benzothienyl, benzimidazolyl, benzoxazolyl, benzthiazolyl, pyridopyridyl, naphthiridinyl, 1H-imidazo[4,5-b]pyridinyl, 3H-imidazo[4,5-b]pyridinyl, imidazo[1,2-a]pyridinyl or 2,3-dihydro-1,4-dioxino[2,3-b]pyridyl; R3 is hydroxyC1 -6alkyl, C1 -6alkoxyC1-6alkyl, cyanoC1-6alkyl, aminocarbonyl-C1 -6-alkyl, mono-or di(C1 -6alkyl)aminocarbonyl-C1 -6- alkyl, carboxyl-C1 -6-alkyl, C1-6alkoxycarbonyl-C1-6 alkyl; R2, R4 and R5 are hydrogen or C1-6alkyl; Het is pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl, furanyl, tetrahydrofuranyl, thienyl, pyrrolyl, thiazolyl, oxazolyl, imidazolyl, isothiazolyl, pyrazolyl, isoxazolyl, oxadiazolyl, quinolinyl, quinoxalinyl, benzofuranyl, benzothienyl, benzimidazolyl, benzoxazo lyl, benzthiazolyl, pyridopyridyl, naphthiridinyl, 1H-imidazo[4,5-b]- pyridinyl, 3H-imidazo[4,5-b]pyridinyl, imidazo[1,2-a]pyridinyl and 2,3-dihydro-1,4- dioxino[2,3-b]pyridyl; Ar is optionally substituted phenyl; pharmaceutical compositions containing compounds (I) and processes for preparing compounds (I).

MORPHOLINYL CONTAINING BENZIMIDAZOLES AS INHIBITORS OF RESPIRATORY SYNCYTIAL VIRUS REPLICATION

The present invention concerns morpholinyl containing benzimidazoles having inhibitory activity on the replication of the respiratory syncytial virus and having the formula (I), a prodrug, N-oxide, addition salt, quaternary amine, metal complex or stereoc