857067-38-0

Basic information

• Product Name: 2-((6-(hydroxyMethyl)-2-((3-Morpholinopropyl)aMino)-1H-benzo[d]iMidazol-1-yl)Methyl)-6-Methylpyridin-3-ol
• Synonyms: 2-((6-(hydroxyMethyl)-2-((3-Morpholinopropyl)aMino)-1H-benzo[d]iMidazol-1-yl)Methyl)-6-Methylpyridin-3-ol;2-((6-(hydroxyMethyl)-2-((3-Morpholinopropyl)aMino)-1H-benzo[d]iMidazol-1-yl)Methyl)-6-Methylpyridin-3-ol-7;2-[[6-(hydroxymethyl)-2-(3-morpholin-4-ylpropylamino)benzimidazol-1-yl]methyl]-6-methylpyridin-3-ol
• CAS NO: 857067-38-0
• Molecular Formula: C22H29N5O3
• Molecular Weight: 411.49736
• Mol File: 857067-38-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-((6-(hydroxyMethyl)-2-((3-Morpholinopropyl)aMino)-1H-benzo[d]iMidazol-1-yl)Methyl)-6-Methylpyridin-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-((6-(hydroxyMethyl)-2-((3-Morpholinopropyl)aMino)-1H-benzo[d]iMidazol-1-yl)Methyl)-6-Methylpyridin-3-ol(857067-38-0)
• EPA Substance Registry System: 2-((6-(hydroxyMethyl)-2-((3-Morpholinopropyl)aMino)-1H-benzo[d]iMidazol-1-yl)Methyl)-6-Methylpyridin-3-ol(857067-38-0)

Safety Data

• Hazardous Substances Data: 857067-38-0(Hazardous Substances Data)

Usage

Molecular structure

Contains a benzimidazole ring, a morpholinopropylamino group, a methylpyridinol moiety, and a hydroxymethyl group.

Chemical classification

It is a derivative of the benzodiazepine class of drugs.

Potential therapeutic applications

May be used in the treatment of anxiety, insomnia, and other psychiatric disorders.

Role of structure and properties

The specific structure and properties of this compound likely play a role in its pharmacological effects.

Further research and testing

Necessary to fully understand the potential therapeutic applications of this compound.

Upstream product

• 37466-90-3 ethyl 3,4-diaminobenzoate 
• 634602-84-9 2-hydroxy-3H-benzoimidazole-5-carboxylic acid ethyl ester 
• 857070-66-7 (2-chloro-3H-benzoimidazol-5-yl)methanol 
• 317847-65-7 2-(chloromethyl)-6-methyl-3-pyridinol 
• 857070-67-8 [2-(3-morpholin-4-ylpropylamino)-3H-benzoimidazol-5-yl]methanol 
• 98280-34-3 2-chloromethyl-6-methyl-pyridin-3-ol hydrochloride 

Downstream Products

• 857070-65-6 3-(3-hydroxy-6-methylpyridin-2-ylmethyl)-2-(3-morpholin-4-ylpropylamino)-3H-benzoimidazole-5-carbaldehyde 

Relevant articles and documents

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