The invention relates to a method for producing an oxysulphidic and fluorinated derivative in the form of a salt of formula (II) Ea-SO.sup.Q.sup.+ (II) comprising providing an ionic liquid compound of formula (I) in the liquid state Ea-SOO.sup.Cr (II)Ea representing the fluorine atom or a group having between 1 and 10 carbon atoms selected from fluoroalkyls, perfluoroalkyls and fluoroalkenyls; andQ.sup.+ representing an onium cation, with a sulphur oxide, said ionic liquid compound of formula (I) representing at least 50 wt. % of the initial liquid reactive medium.

The invention relates to a method for producing an oxysulphidic and fluorinated derivative in the form of a salt of formula (II) Ea-SO.sup.Q.sup.+ (II) comprising providing an ionic liquid compound of formula (I) in the liquid state Ea-SOO.sup.Cr (II)Ea representing the fluorine atom or a group having between 1 and 10 carbon atoms selected from fluoroalkyls, perfluoroalkyls and fluoroalkenyls; andQ.sup.+ representing an onium cation, with a sulphur oxide, said ionic liquid compound of formula (I) representing at least 50 wt. % of the initial liquid reactive medium.

The invention relates to a method for producing an oxysulphidic and fluorinated derivative in the form of a salt of formula (II) Ea-SO.sup.Q.sup.+ (II) comprising providing an ionic liquid compound of formula (I) in the liquid state Ea-SOO.sup.Cr (II)Ea representing the fluorine atom or a group having between 1 and 10 carbon atoms selected from fluoroalkyls, perfluoroalkyls and fluoroalkenyls; andQ.sup.+ representing an onium cation, with a sulphur oxide, said ionic liquid compound of formula (I) representing at least 50 wt. % of the initial liquid reactive medium.

The present disclosure relates to the preparation of a compound of formula (I) comprising an SO.sub.2F function, RSO.sub.2F, by reacting a compound of formula (II), RSO.sub.2X, with a fluorinating agent, the process carried out in the liquid phase in the presence of hydrofluoric acid using an antimony-based fluorination catalyst, wherein R, R, and X are described herein.

The present disclosure relates to the preparation of a compound of formula (I) comprising an SO.sub.2F function, RSO.sub.2F, by reacting a compound of formula (II), RSO.sub.2X, with a fluorinating agent, the process carried out in the liquid phase in the presence of hydrofluoric acid using an antimony-based fluorination catalyst, wherein R, R, and X are described herein.

The present disclosure relates to the preparation of a compound of formula (I) comprising an SO.sub.2F function, RSO.sub.2F, by reacting a compound of formula (II), RSO.sub.2X, with a fluorinating agent, the process carried out in the liquid phase in the presence of hydrofluoric acid using an antimony-based fluorination catalyst, wherein R, R, and X are described herein.

Described herein is a novel series of multi-fluoro-substituted pyrazolopyrimidine compounds or salts thereof. These compounds are Bruton's tyrosine kinase (BTK) inhibitors. These compounds may possess better BTK inhibition selectivity and pharmacokinetic properties. Disclosed herein are the synthesis methods of these compounds. Disclosed herein are novel synthesis methods of the multi-fluoro-substituted benzophenone and substituted phenoxy benzene. Also disclosed are pharmaceutical compositions comprising the BTK inhibitors described herein. The present invention also relates to pharmaceutical formulations comprising the compounds described herein as active ingredients. The present invention also includes the therapeutic methods by administering the BTK inhibitors and their formulations to treat and inhibit autoimmune disease, hypersensitivity disease, inflammatory diseases and cancer.

Described herein is a novel series of multi-fluoro-substituted pyrazolopyrimidine compounds or salts thereof. These compounds are Bruton's tyrosine kinase (BTK) inhibitors. These compounds may possess better BTK inhibition selectivity and pharmacokinetic properties. Disclosed herein are the synthesis methods of these compounds. Disclosed herein are novel synthesis methods of the multi-fluoro-substituted benzophenone and substituted phenoxy benzene. Also disclosed are pharmaceutical compositions comprising the BTK inhibitors described herein. The present invention also relates to pharmaceutical formulations comprising the compounds described herein as active ingredients. The present invention also includes the therapeutic methods by administering the BTK inhibitors and their formulations to treat and inhibit autoimmune disease, hypersensitivity disease, inflammatory diseases and cancer.

A multi-acid monomer disclosed herein has the formula ##STR00001##
wherein R is one or more units of a non-SO.sub.2F or non-SO.sub.2Cl portion of a polymer precursor in sulfonyl fluoride or sulfonyl chloride form, X is a non-sulfonyl halide group of a multi-sulfonyl halide compound having a minimum of two acid giving groups, and Y is remaining sulfonyl halide groups of the multi-sulfonyl halide compound.

A multi-acid monomer disclosed herein has the formula ##STR00001##
wherein R is one or more units of a non-SO.sub.2F or non-SO.sub.2Cl portion of a polymer precursor in sulfonyl fluoride or sulfonyl chloride form, X is a non-sulfonyl halide group of a multi-sulfonyl halide compound having a minimum of two acid giving groups, and Y is remaining sulfonyl halide groups of the multi-sulfonyl halide compound.