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Publication Number
US-12065436-B2
Publication Date
2024-08-20
Expiration Date
Abstract
Provided are compounds of Formula (I): or a pharmaceutically acceptable salt thereof, wherein A, Z, B, R1, R2, R3, G1, G2, and G3 are as defined herein. Also provided is a pharmaceutically acceptable composition comprising a compound of Formula (I), or a pharmaceutically acceptable salt thereof.Also provided are methods of using a compound of Formula (I), or a pharmaceutically acceptable salt thereof.
Core Innovation
The disclosure describes a method of preparing a compound of formula (A) or a salt thereof by converting a compound of formula (15-3) or a salt thereof into the compound of formula (A) or a salt thereof. The method is further refined by specified reagents and upstream intermediate conversions, including compounds of formulas (15-2), (5-4), (5-3), and (5-2).
The conversion of formula (15-3) to formula (A) is carried out by reacting with 1-methyl-1H-pyrazole-4-carboxylic acid or a salt thereof, in the presence of HOAt and EDCI. Additional intermediate steps include conversion of formula (5-4) with propanoyl propanoate at a temperature of about 105°C, conversion of formula (5-2) to formula (5-3) with K4Fe(CN)6·3H2O, and conversion of (1R)-5-bromo-2,3-dihydro-1H-inden-1-amine hydrochloride to formula (5-2) with di-tert-butyl dicarbonate.
The compound examples described in the inputs include substituted indane and benzofuran scaffolds linked to 1,2,4-oxadiazole, isoxazole, pyrazole, tetrazole, and related heteroaryl carboxamide motifs. The examples include (R)- and (S)-configured compounds, isotopically labeled analogs, and substituent variation such as ethyl, methyl, cyclopropyl, cyclobutyl, difluoromethyl, methoxymethyl, hydroxyethyl, and other heteroaryl substitutions.
Claims Coverage
The provided claim coverage centers on one independent method claim. It covers preparing a compound of formula (A) or a salt thereof by converting a compound of formula (15-3) or a salt thereof into the compound of formula (A) or a salt thereof, with multiple dependent claims specifying reagents and intermediate conversion steps.
Converting formula (15-3) to formula (A)
A method of preparing a compound of formula (A) or a salt thereof by converting a compound of formula (15-3) or a salt thereof to the compound of formula (A) or a salt thereof.
Using 1-methyl-1H-pyrazole-4-carboxylic acid
The conversion of the compound of formula (15-3) or a salt thereof to the compound of formula (A) or a salt thereof is performed by reacting with 1-methyl-1H-pyrazole-4-carboxylic acid or a salt thereof.
Using HOAt and EDCI
The reaction with 1-methyl-1H-pyrazole-4-carboxylic acid or a salt thereof is performed in the presence of HOAt and EDCI.
Intermediate conversion at about 105°C
Reacting the compound of formula (5-4) or a salt thereof with propanoyl propanoate is performed at a temperature of about 105°C.
Using K4Fe(CN)6·3H2O
Converting the compound of formula (5-2) or a salt thereof to the compound of formula (5-3) or its salt comprises reacting the compound of formula (5-2) or its salt with K4Fe(CN)6·3H2O.
Using di-tert-butyl dicarbonate
Converting (1R)-5-bromo-2,3-dihydro-1H-inden-1-amine hydrochloride or a salt thereof to the compound of formula (5-2) or a salt thereof comprises reacting (1R)-5-bromo-2,3-dihydro-1H-inden-1-amine or its salt with di-tert-butyl dicarbonate.
Overall, the claims are directed to converting formula (15-3) into formula (A), with dependent claims specifying 1-methyl-1H-pyrazole-4-carboxylic acid, HOAt, EDCI, K4Fe(CN)6·3H2O, di-tert-butyl dicarbonate, and an about 105°C condition for one intermediate step.
Stated Advantages
Not explicitly described in patent.
Documented Applications
Not explicitly described in patent.
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