The present invention is related to new pyrrole derivatives in the manufacture of a medicament for preventing or treating malaria. Specifically, the present invention is related to pyrrole derivatives useful for the preparation of a pharmaceutical formulation for the inhibition of malaria parasite proliferation.

Disclosed by the present application is a crystalline form of a capsid protein assembly inhibitor containing an N hetero five-membered ring; specifically disclosed is the crystalline form of the compound of formula I; also comprised is an the application of said crystalline form in the preparation of a drug for preventing or treating diseases benefiting from the inhibition of capsid protein assembly.

##STR00001##

Disclosed by the present application is a crystalline form of a capsid protein assembly inhibitor containing an N hetero five-membered ring; specifically disclosed is the crystalline form of the compound of formula I; also comprised is an the application of said crystalline form in the preparation of a drug for preventing or treating diseases benefiting from the inhibition of capsid protein assembly.

##STR00001##

A process A for the production of compounds of formula I is provided. ##STR00001## Process A includes Step A of reacting compounds of formula II ##STR00002##
with 2,3-dihalopropionitrile or 2-haloacrylonitrile in the presence of DIPEA. A process B for the production of compounds of formula III is also provided. ##STR00003## Process B includes Step B of reacting compounds of formula I with Br.sub.2 in the presence of DIPEA. A process C for the production of compounds of formula IV is further provided. ##STR00004## Process C includes Step C of reacting compounds of formula III with di(C.sub.1-C.sub.4-alkoxy)methane and either POCl.sub.3, or a mixture comprising POCl.sub.3 and DMF, in the presence of DIPEA. Additionally, the use of DIPEA as a base in the production of compounds of formula I, compounds of formula III, or compounds of formula IV is provided.

A process A for the production of compounds of formula I is provided. ##STR00001## Process A includes Step A of reacting compounds of formula II ##STR00002##
with 2,3-dihalopropionitrile or 2-haloacrylonitrile in the presence of DIPEA. A process B for the production of compounds of formula III is also provided. ##STR00003## Process B includes Step B of reacting compounds of formula I with Br.sub.2 in the presence of DIPEA. A process C for the production of compounds of formula IV is further provided. ##STR00004## Process C includes Step C of reacting compounds of formula III with di(C.sub.1-C.sub.4-alkoxy)methane and either POCl.sub.3, or a mixture comprising POCl.sub.3 and DMF, in the presence of DIPEA. Additionally, the use of DIPEA as a base in the production of compounds of formula I, compounds of formula III, or compounds of formula IV is provided.

The present invention provides a production method of a sulfonylpyrrole compound useful as a pharmaceutical product, a production method of an intermediate used for the method, and a novel intermediate. The present invention relates to a method of producing sulfonylpyrrole compound (VIII), which includes reducing compound (III) and hydrolyzing the reduced product to give compound (IV), subjecting compound (IV) to a sulfonylation reaction to give compound (VI), and subjecting compound (VI) to an amination reaction. ##STR00001##

The present invention provides a production method of a sulfonylpyrrole compound useful as a pharmaceutical product, a production method of an intermediate used for the method, and a novel intermediate. The present invention relates to a method of producing sulfonylpyrrole compound (VIII), which includes reducing compound (III) and hydrolyzing the reduced product to give compound (IV), subjecting compound (IV) to a sulfonylation reaction to give compound (VI), and subjecting compound (VI) to an amination reaction. ##STR00001##

An object is to provide a compound having β-lactamase inhibitory activity. The object is achieved by a compound represented by formula (1), typified by a compound in which specific positions of a 5-membered ring having planarity are replaced by sulfamoyl and carboxy groups.

An object is to provide a compound having β-lactamase inhibitory activity. The object is achieved by a compound represented by formula (1), typified by a compound in which specific positions of a 5-membered ring having planarity are replaced by sulfamoyl and carboxy groups.

Substituted phenylpyrrolecarboxamide compounds such as those represented by Formula A can be used in the treatment of HIV infection and related conditions.