An intermediate of a polyamine derivative, a preparation method therefor, and a use thereof. The intermediate is easy to prepare and high in purity; and when the intermediate is used for preparing the polyamine derivative, the obtained product is high in purity, the operation is simple and convenient, the purity and yield of the polyamine derivative are improved, the purification operation for the product is simplified, and the industrial production of the polyamine derivative and a medicinal salt thereof can be improved. Further provided is a preparation method for the polyamine derivative, the operation thereof is simple and convenient, and the purity of the obtained product is high. The method has a very good application prospect in the field of chemical medicines.

An intermediate of a polyamine derivative, a preparation method therefor, and a use thereof. The intermediate is easy to prepare and high in purity; and when the intermediate is used for preparing the polyamine derivative, the obtained product is high in purity, the operation is simple and convenient, the purity and yield of the polyamine derivative are improved, the purification operation for the product is simplified, and the industrial production of the polyamine derivative and a medicinal salt thereof can be improved. Further provided is a preparation method for the polyamine derivative, the operation thereof is simple and convenient, and the purity of the obtained product is high. The method has a very good application prospect in the field of chemical medicines.

The present invention provides, in part, di-thioester cationic lipid compounds or a pharmaceutically acceptable salt thereof. The compounds provided herein can be useful for delivery and expression of mRNA and encoded protein, e.g., as a component of liposomal delivery vehicle, and accordingly can be useful for treating various diseases, disorders and conditions, such as those associated with deficiency of one or more proteins.

The present invention provides a production method capable of synthesizing an aryl thiol ester compound under mild conditions rapidly at a high yield. The present invention provides a method for producing an aryl thiol ester compound including producing an aryl thiol ester compound represented by the following general formula (1) from a diazonium compound represented by the following general formula (2) and a thioate compound represented by the following general formula (3) by a Sandmeyer-type coupling reaction using a catalyst, [wherein A.sup.1 and A.sup.2 are each independently an optionally substituted aryl group or an optionally substituted heteroaryl group; X.sup.1 is a monovalent anion; and M.sup.1 is a monovalent cation].

##STR00001##

The present invention provides a production method capable of synthesizing an aryl thiol ester compound under mild conditions rapidly at a high yield. The present invention provides a method for producing an aryl thiol ester compound including producing an aryl thiol ester compound represented by the following general formula (1) from a diazonium compound represented by the following general formula (2) and a thioate compound represented by the following general formula (3) by a Sandmeyer-type coupling reaction using a catalyst, [wherein A.sup.1 and A.sup.2 are each independently an optionally substituted aryl group or an optionally substituted heteroaryl group; X.sup.1 is a monovalent anion; and M.sup.1 is a monovalent cation].

##STR00001##

The present invention provides a production method capable of efficiently synthesizing an SF.sub.5 group-containing compound, or the like. The present invention is a method for synthesizing an SF.sub.5 group-containing compound represented by the general formula (1) from a thioaryl compound represented by the general formula (2) [A.sup.1 is an aryl group or a heteroaryl group; G.sup.1 is SH, SCN, SF.sub.3, SSR.sup.1, SCOR.sup.2, SR.sup.3, SF.sub.2R.sup.4, SSi(R.sup.5).sub.3, SPO(R.sup.6).sub.2, (N-phthalimidyl)thio group, or a thianthrenium group (R.sup.1 is an aryl group or a heteroaryl group; R.sup.2 and R.sup.5 are an aryl group, a heteroaryl group, an alkyl group, or an alkenyl group; R.sup.3 and R.sup.4 are an alkyl group or an alkenyl group, R.sup.6 is an aryloxy group, a heteroaryloxy group, an alkyloxy group, or an alkenyloxy group)].

[Chemical Formula 1]

A.sup.1G.sup.1(2)

A.sup.1SF.sub.5(1)

The present invention provides a production method capable of efficiently synthesizing an SF.sub.5 group-containing compound, or the like. The present invention is a method for synthesizing an SF.sub.5 group-containing compound represented by the general formula (1) from a thioaryl compound represented by the general formula (2) [A.sup.1 is an aryl group or a heteroaryl group; G.sup.1 is SH, SCN, SF.sub.3, SSR.sup.1, SCOR.sup.2, SR.sup.3, SF.sub.2R.sup.4, SSi(R.sup.5).sub.3, SPO(R.sup.6).sub.2, (N-phthalimidyl)thio group, or a thianthrenium group (R.sup.1 is an aryl group or a heteroaryl group; R.sup.2 and R.sup.5 are an aryl group, a heteroaryl group, an alkyl group, or an alkenyl group; R.sup.3 and R.sup.4 are an alkyl group or an alkenyl group, R.sup.6 is an aryloxy group, a heteroaryloxy group, an alkyloxy group, or an alkenyloxy group)].

[Chemical Formula 1]

A.sup.1G.sup.1(2)

A.sup.1SF.sub.5(1)

The present invention provides, in part, di-thioester cationic lipid compounds or a pharmaceutically acceptable salt thereof. The compounds provided herein can be useful for delivery and expression of mRNA and encoded protein, e.g., as a component of liposomal delivery vehicle, and accordingly can be useful for treating various diseases, disorders and conditions, such as those associated with deficiency of one or more proteins.