209286-73-7

Usage

Uses

Used in Pharmaceutical Industry:
1-Chloro-6-methylisoquinoline is used as a key intermediate in the synthesis of 5-membered aminoheterocyclic and 5,6or 6,6-membered bicyclic aminoheterocyclic inhibitors of ROCK (Rho-associated protein kinase). These inhibitors play a significant role in the treatment of heart failure by modulating the ROCK signaling pathway, which is involved in the regulation of cardiac function and remodeling.

InChI:InChI=1/C10H8ClN/c1-7-2-3-9-8(6-7)4-5-12-10(9)11/h2-6H,1H3

Upstream product

• 70810-28-5 6-methylisoquinoline N-oxide 
• 131002-10-3 6-methyl-2H-isoquinolin-1-one 
• 108-95-2 phenol 
• 42398-73-2 6-methylisoquinoline 
• 131002-10-3 6-methyl-isoquinolin-1-ol 

Downstream Products

• 234109-25-2 C₁₀H₇BrClN 
• 950516-24-2 C₁₀H₉ClN₂ 

Relevant academic research and scientific papers

Regioselective Chlorination of Quinoline N-Oxides and Isoquinoline N-Oxides Using PPh3/Cl3CCN

A novel method for the regioselective C2-chlorination of heterocyclic N-oxides has been developed. PPh3/Cl3CCN were used as chlorinating reagents and the desired N-heterocyclic chlorides were obtained smoothly in satisfactory yields. The reactions proceeded in a highly efficient and selective manner across a broad range of substrates demonstrating excellent functional group tolerance. In addition, this chlorination reaction can be used for the modification of N-heterocyclic scaffolds of appealing ligands and pharmaceuticals.

A practical and mild chlorination of fused heterocyclic N-oxides

Fused azine N-oxides were selectively chlorinated at C2 in moderate to excellent yields, employing Vilsmeier reagent as both the activating agent and the nucleophilic chloride source. Remarkable features of the method include simple operation, mild reaction conditions, a wide substrate scope, and the use of only stoichiometric amount of POCl3. The potential extension of this method to a one-pot oxidation/chlorination sequence that obviates the need for isolation of the N-oxide intermediates is also validated.

Design, synthesis, and biological evaluation of pyrazinones containing novel P1 needles as inhibitors of TF/VIIa

Herein is described the design, synthesis, and enzymatic activity of a series of substituted pyrazinones as inhibitors of the TF/VIIa complex. These inhibitors were designed to explore replacement and variation of the P1 amidine described previously [J. Med. Chem. 2003, 46, 4050]. The P1 needle replacements were selected based upon their reduced basicity compared to the parent phenyl amidine (pKa ～ 12). A contributing factor towards the oral bioavailability of a compound is the ionization state of the compound in the intestinal tract. The desired outcome of the study was to identify an orally bioavailable TF-VIIa inhibitor.

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.

Sulfonic acid sulfonylamino n-(heteroaralkyl)-azaheterocyclylamide compounds

The compounds of formula I herein exhibit useful pharmacological activity and accordingly are incorporated into pharmaceutical compositions and used in the treatment of patients suffering from certain medical disorders. More specifically, they are inhibitors of the activity of Factor Xa. The present invention is directed to compounds of formula I, compositions containing compounds of formula I, and their use, for treating a patient suffering from, or subject to, a physiological condition which can be ameliorated by the administration of an inhibitor of the activity of Factor Xa.

Isoquinolines as urokinase inhibitors

Compounds of formula (I): and pharmaceutically acceptable salts thereof, wherein one of R1 and R2 is H and the other is N=C(NH2)2 or NHC(=NH)NH2, and the other substituents are as defined herein, are urokinase (uPA) inhibitors.