24188-74-7

Usage

Uses

Used in Pharmaceutical Industry:
7-CHLORO-1-HYDROXYISOQUINOLINE is used as a reagent for the preparation of various compounds, including methoxyisoquinoline derivatives. It plays a crucial role in the synthesis of asunaprevir (BMS-650032), an orally efficacious NS3 protease inhibitor, which is utilized for the treatment of hepatitis C virus infection. This application highlights the compound's importance in the development of antiviral medications.
Used in Medicinal Chemistry Research:
7-CHLORO-1-HYDROXYISOQUINOLINE is employed as a key intermediate in the synthesis and pharmacological evaluation of a series of 1,2-dihydro-1-[(5-methyl-1-imidazol-4-yl)methyl]-2-oxopyridine 5-HT3 antagonists. These antagonists are significant in the field of medicinal chemistry, as they have the potential to be developed into new drugs for the treatment of various disorders related to the serotonin system, such as anxiety, depression, and gastrointestinal disorders.

InChI:InChI=1/C9H6ClNO/c10-7-2-1-6-3-4-11-9(12)8(6)5-7/h1-5H,(H,11,12)

Upstream product

• 21663-61-6 2,5-dichlorobenzonitrile 
• 1028252-12-1 C₁₁H₁₃ClN₂O 
• 50712-70-4 5-chloro-2-methylbenzonitrile 
• 83421-78-7 (E)-3-(4-Chloro-phenyl)-acryloyl azide 
• 70810-26-3 7-chloroisoquinoline 2-oxide 
• 21900-40-3 5-chloro-2-methylbenzoyl chloride 
• 7499-06-1 5-chloro-2-methylbenzoic acid 
• 1028252-11-0 5-chloro-2-methylbenzamide 
• 1615-02-7 p-chlorocinnamic acid 
• 131002-02-3 2-bromo-5-chlorobenzamide 
• 130874-98-5 5-chloro-2-<(E)-2-(dimethylamino)vinyl>benzonitrile 
• 131002-05-6 5-chloro-2-ethenylbenzamide 

Downstream Products

• 630420-16-5 tert-butyl ((S)-1-((2S,4R)-4-((7-chloro-4-methoxyisoquinolin-1-yl)oxy)-2-(((1R,2S)-1-((cyclopropylsulfonyl)carbamoyl)-2-vinylcyclopropyl)carbamoyl)pyrrolidin-1-yl)-3,3-dimethyl-1-oxobutan-2-yl)carbamate 
• 1028252-15-4 (2S,4R)-1-(tert-butoxycarbonyl)-4-((7-chloro-4-methoxyisoquinolin-1-yl)oxy)pyrrolidine-2-carboxylic acid 
• 953421-74-4 4-bromo-1,7-dichloroisoquinoline 
• 630423-36-8 1,7-dichloro-4-methoxyisoquinoline 
• 1169846-35-8 (2S,4R)-4-((7-chloro-4-methoxyisoquinolin-1-yl)oxy)-N-((1R,2S)-1-((cyclopropylsulfonyl)carbamoyl)-2-vinylcyclopropyl)pyrrolidine-2-carboxamide hydrochloride 
• 70810-24-1 1,7-dichloroisoquinoline 
• 630423-35-7 7-chloro-4-methoxy-2H-isoquinolin-1-one 

Relevant academic research and scientific papers

The discovery of asunaprevir (BMS-650032), an orally efficacious NS3 protease inhibitor for the treatment of hepatitis C virus infection

The discovery of asunaprevir (BMS-650032, 24) is described. This tripeptidic acylsulfonamide inhibitor of the NS3/4A enzyme is currently in phase III clinical trials for the treatment of hepatitis C virus infection. The discovery of 24 was enabled by employing an isolated rabbit heart model to screen for the cardiovascular (CV) liabilities (changes to HR and SNRT) that were responsible for the discontinuation of an earlier lead from this chemical series, BMS-605339 (1), from clinical trials. The structure-activity relationships (SARs) developed with respect to CV effects established that small structural changes to the P2* subsite of the molecule had a significant impact on the CV profile of a given compound. The antiviral activity, preclincial PK profile, and toxicology studies in rat and dog supported clinical development of BMS-650032 (24).

Synthesis of Isoquinolones by Sequential Suzuki Coupling of 2-Halobenzonitriles with Vinyl Boronate Followed by Cyclization

A novel, facile, and expeditious two-step synthesis of 3,4-unsubstituted isoquinolin-1(2H)-ones from a Suzuki cross-coupling between 2-halobenzonitriles and commercially available vinyl boronates followed by platinum-catalyzed nitrile hydrolysis and cyclization is described.

GLYCOLATE OXIDASE INHIBITORS FOR THE TREATMENT OF DISEASE

Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or disorders associated with a defect in glyoxylate metabolism, for example a disease or disorder associated with the enzyme glycolate oxidase (GO) or alterations in oxalate metabolism. Such diseases or disorders include, for example, disorders of glyoxylate metabolism, including primary hyperoxaluria, that are associated with production of excessive amounts of oxalate.

GLYCOLATE OXIDASE INHIBITORS FOR THE TREATMENT OF DISEASE

Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or disorders associated with the enzyme glycolate oxidase (GO). Such diseases or disorders include, for example, disorders of glyoxylate metabolism, including primary hyperoxaluria, that are associated with production of excessive amounts of oxalate.

Process for Synthesizing Substituted Isoquinolines

The present disclosure generally relates to a process for synthesizing optionally substituted 1-chloro-4-methoxyisoquinolines. The present disclosure also relates to intermediates useful in this process.

Hepatitis C Virus Inhibitors

Hepatitis C virus inhibitors having the general formula are disclosed. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.

Hepatitis C Virus Inhibitors

Hepatitis C virus inhibitors having the general formula are disclosed. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.

Hepatitis C Virus Inhibitors

Hepatitis C virus inhibitors having the general formula are disclosed. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.

HEPATITIS C VIRUS INHIBITORS

Hepatitis C virus inhibitors are disclosed having the general formula:(I) wherein R1, R2, R3, R', B, Y and X are described in the description. Compositions comprising the compounds and methods for using the compounds toinhibit HCV are also disclosed.

Synthesis of novel substituted isoquinolones

A series of novel substituted isoquinolones have been synthesised. This has been achieved by two routes, either Curtius rearrangment of cinnamic acids or via an isoquinoline N-oxide.