446284-32-8

Usage

Uses

Used in Pharmaceutical Drug Development:
7-Chloro-4-methoxy-1H-pyrrolo[2,3-c]pyridine is utilized as a key intermediate in the development of pharmaceutical drugs, particularly within the field of medicinal chemistry. Its unique structural features make it a valuable building block for the synthesis of diverse bioactive molecules and pharmaceuticals.
Used in Organic Synthesis:
In the realm of organic synthesis, 7-Chloro-4-methoxy-1H-pyrrolo[2,3-c]pyridine serves as a reagent or intermediate. Its presence in various synthesis processes highlights its versatility and importance in creating a wide range of chemical compounds.

Upstream product

• 124-41-4 sodium methylate 
• 425380-38-7 4-bromo-7-chloro-3a,7a-dihydro-1H-pyrrolo[2,3-c]pyridine 
• 67-56-1 methanol 
• 917918-80-0 C₈H₈N₂O₂ 
• 452296-79-6 4,7-dimethoxy-1H-pyrrolo[2,3-c]pyridine 
• 67443-38-3 5-bromo-2-chloro-3-nitropyridine 
• 917918-80-0 7-hydroxy-4-methoxy-6-azaindole 

Downstream Products

• 1426310-90-8 1-(5-benzoylhexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)-2-(4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)ethane-1,2-dione 
• 701213-36-7 1-(4-benzoylpiperazin-1-yl)-2-(4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-ethane-1,2-dione 
• 864953-39-9 1,3-dihydroxy-2-(hydroxymethyl)propan-2-aminium (3-(2-(4-benzoylpiperazin-1-yl)-2-oxoacetyl)-4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-1-yl)methyl hydrogen phosphate 
• 701213-73-2 (R)-1-(4-benzoyl-3-methylpiperazin-1-yl)-2-(7-chloro-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)ethane-1,2-dione 
• 446289-32-3 N-(5-(3-(2-(4-benzoylpiperazin-1-yl)-2-oxoacetyl)-4-methoxy-1H-pyrrolo[2,3-c]pyridin-7-yl)thiazol-2-yl)acetamide 
• 446289-94-7 1-(7-(2-aminothiazol-5-yl)-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-(4-benzoylpiperazin-1-yl)ethane-1,2-dione 
• 619330-81-3 1-(4-benzoylpiperazin-1-yl)-2-(4-methoxy-7-(1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)ethane-1,2-dione 
• 701212-80-8 (R)-1-(4-benzoyl-3-methylpiperazin-1-yl)-2-(4-methoxy-7-(1H-1,2,3-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)ethane-1,2-dione 
• 701212-64-8 (R)-1-(4-benzoyl-3-methylpiperazin-1-yl)-2-(7-(3-((dimethylamino)methyl)-1H-pyrazol-1-yl)-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)ethane-1,2-dione 
• 701213-60-7 1-(4-benzoylpiperazin-1-yl)-2-(7-(4-fluoro-1H-pyrazol-1-yl)-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)ethane-1,2-dione 
• 701213-01-6 1-(3-(2-(4-benzoylpiperazin-1-yl)-2-oxoacetyl)-4-methoxy-1H-pyrrolo[2,3-c]pyridin-7-yl)-N-methyl-1H-pyrazole-3-carboxamide 
• 701212-99-9 1-(3-(2-(4-benzoylpiperazin-1-yl)-2-oxoacetyl)-4-methoxy-1H-pyrrolo[2,3-c]pyridin-7-yl)-N-methyl-1H-1,2,4-triazole-3-carboxamide 
• 701212-98-8 1-(3-(2-(4-benzoylpiperazin-1-yl)-2-oxoacetyl)-4-methoxy-1H-pyrrolo[2,3-c]pyridin-7-yl)-N-ethyl-1H-1,2,4-triazole-3-carboxamide 
• 701213-00-5 1-(3-(2-(4-benzoylpiperazin-1-yl)-2-oxoacetyl)-4-methoxy-1H-pyrrolo[2,3-c]pyridin-7-yl)-N,N-dimethyl-1H-1,2,4-triazole-3-carboxamide 

Relevant academic research and scientific papers

Discovery of the Human Immunodeficiency Virus Type 1 (HIV-1) Attachment Inhibitor Temsavir and Its Phosphonooxymethyl Prodrug Fostemsavir

The optimization of the 4-methoxy-6-azaindole series of HIV-1 attachment inhibitors (AIs) that originated with 1 to deliver temsavir (3, BMS-626529) is described. The most beneficial increases in potency and pharmacokinetic (PK) properties were attained by incorporating N-linked, sp2-hybridized heteroaryl rings at the 7-position of the heterocyclic nucleus. Compounds that adhered to a coplanarity model afforded targeted antiviral potency, leading to the identification of 3 with characteristics that provided for targeted exposure and PK properties in three preclinical species. However, the physical properties of 3 limited plasma exposure at higher doses, both in preclinical studies and in clinical trials as the result of dissolution- and/or solubility-limited absorption, a deficiency addressed by the preparation of the phosphonooxymethyl prodrug 4 (BMS-663068, fostemsavir). An extended-release formulation of 4 is currently in phase III clinical trials where it has shown promise as part of a drug combination therapy in highly treatment-experienced HIV-1 infected patients.

Kinetic characterization of novel HIV-1 entry inhibitors: Discovery of a relationship between off-rate and potency

The entry of HIV-1 into permissible cells remains an extremely attractive and underexploited therapeutic intervention point. We have previously demonstrated the ability to extend the chemotypes available for optimization in the entry inhibitor class using computational means. Here, we continue this effort, designing and testing three novel compounds with the ability to inhibit HIV-1 entry. We demonstrate that alteration of the core moiety of these entry inhibitors directly influences the potency of the compounds, despite common proximal and distal groups. Moreover, by establishing for the first time a surface plasmon resonance (SPR)-based interaction assay with soluble recombinant SOSIP Env trimers, we demonstrate that the off-rate (kd) parameter shows the strongest correlation with potency in an antiviral assay. Finally, we establish an underappreciated relationship between the potency of a ligand and its degree of electrostatic complementarity (EC) with its target, the Env complex. These findings not only broaden the chemical space in this inhibitor class, but also establish a rapid and simple assay to evaluate future HIV-1 entry inhibitors.

Core chemotype diversification in the HIV-1 entry inhibitor class using field-based bioisosteric replacement

Demand remains for new inhibitors of HIV-1 replication and the inhibition of HIV-1 entry is an extremely attractive therapeutic approach. Using field-based bioisosteric replacements, we have further extended the chemotypes available for development in the HIV-1 entry inhibitor class. Moreover, using field-based disparity analysis of the compounds, 3D structure-activity relationships were derived that will be useful in the further development of these inhibitors towards clinical utility.

Discovery and optimization of novel small-molecule HIV-1 entry inhibitors using field-based virtual screening and bioisosteric replacement

With the emergence of drug-resistant strains and the cumulative toxicities associated with current therapies, demand remains for new inhibitors of HIV-1 replication. The inhibition of HIV-1 entry is an attractive, yet underexploited therapeutic approach with implications for salvage and preexposure prophylactic regimens, as well as topical microbicides. Using the combination of a field-derived bioactive conformation template to perform virtual screening and iterative bioisosteric replacements, coupled with in silico predictions of absorption, distribution, metabolism, and excretion, we have identified new leads for HIV-1 entry inhibitors.

DIKETO-PIPERAZINE AND PIPERIDINE DERIVATIVES AS ANTIVIRAL AGENTS

This disclosure provides compounds having drug and bio-affecting properties, their pharmaceutical compositions and method of use. In particular, the disclosure is concerned with diketo piperazine and piperadine derivatives that possess unique antiviral activity. More particularly, the present disclosure relates to compounds useful for the treatment of HIV and AIDS.

Prodrugs of piperazine and substituted piperidine antiviral agents

This invention provides for prodrug Compounds I, pharmaceutical compositions thereof, and their use in treating HIV infection. wherein: X is C or N with the proviso that when X is N, R1 does not exist; W is C or N with the proviso that when W is N, R2 does not exist; V is C; E is hydrogen or a pharmaceutically acceptable salt thereof; and Y is selected from the group consisting of Also, this invention provides for intermediate Compounds II useful in making prodrug Compounds I. wherein: L and M are independently selected from the group consisting of C1-C6 alkyl, phenyl, benzyl, trialkylsilyl, -2,2,2-trichloroethoxy and 2-trimethylsilylethoxy.

Composition and antiviral activity of substituted azaindoleoxoacetic piperazine derivatives

This invention provides compounds having drug and bio-affecting properties, their pharmaceutical compositions and method of use. In particular, the invention is concerned with azaindoleoxoacetyl piperazine derivatives. These compounds possess unique antiviral activity, whether used alone or in combination with other antivirals, antiinfectives, immunomodulators or HIV entry inhibitors. More particularly, the present invention relates to the treatment of HIV and AIDS.