To develop a protecting group that facilitates separation and purification, after reaction, of a compound including a protected functional group, without solidifying or insolubilizing the compound.

A xanthene compound of by General Formula (1)

##STR00001## (wherein Y is OR.sup.17 (R.sup.17 is a hydrogen atom or an active ester-protecting group), NHR.sup.18 (R.sup.18 is a hydrogen atom, or a linear or branched C.sub.1-C.sub.6 alkyl group or aralkyl group), an azide, a halogen atom, or a carbonyl group formed together with a methylene group; at least one of R.sup.1 to R.sup.8 is represented by Formula (2);

OR.sup.9X-A(2) and a residue is a hydrogen atom, a halogen atom, a C.sub.1-C.sub.4 alkyl group, or a C.sub.1-C.sub.4 alkoxy group, wherein R.sup.9 is a linear or branched C.sub.1-C.sub.16 alkylene group; X is O or CONR.sup.19 (R.sup.19 is a hydrogen atom or a C.sub.1-C.sub.4 alkyl group); and A is represented by Formula (3) or the like

##STR00002## (wherein R.sup.10, R.sup.11, and R.sup.12, the same or different, are a linear or branched C.sub.1-C.sub.6 alkyl group or an aryl group optionally including a substituent; R.sup.13 is a single bond or a linear or branched C.sub.1-C.sub.3 alkylene group; and R.sup.14, R.sup.15, and R.sup.16 are a linear or branched C.sub.1-C.sub.3 alkylene group)).

The invention relates to a new enantioselective process for producing useful intermediates for the manufacture of NEP inhibitors or prodrugs thereof, in particular NEP inhibitors comprising a -amino--biphenyl--methylalkanoic acid, or acid ester, backbone.

The present invention relates to a pseudo-ceramide compound and a preparation method therefor. According to the present invention, the pseudo-ceramide compound has a molecular structure and a function similar to those of a natural ceramide, can be readily synthesized, and has excellent solubility in an organic solvent and excellent stability, and thus the pseudo-ceramide compound can be used as an alternative to a natural ceramide. Therefore, the pseudo-ceramide compound of the present invention can be widely applied to a skin preparation for external use, a cosmetic composition, and the like for reinforcing and maintaining a skin barrier function.

The present invention relates to a pseudo-ceramide compound and a preparation method therefor. According to the present invention, the pseudo-ceramide compound has a molecular structure and a function similar to those of a natural ceramide, can be readily synthesized, and has excellent solubility in an organic solvent and excellent stability, and thus the pseudo-ceramide compound can be used as an alternative to a natural ceramide. Therefore, the pseudo-ceramide compound of the present invention can be widely applied to a skin preparation for external use, a cosmetic composition, and the like for reinforcing and maintaining a skin barrier function.

An object of the present invention is to develop a protecting group, which can prevent solidification or insolubilization of a compound by protecting a functional group to achieve easy separation and purification after a reaction.

A diphenylmethane compound represented by general formula (1):

##STR00001## wherein Y represents OR.sup.19 (wherein R.sup.19 represents a hydrogen atom or an active ester-type protecting group), NHR.sup.20 (wherein R.sup.20 represents, for example, a hydrogen atom, a C.sub.1-6 linear or branched alkyl group, or an aralkyl group, at least one of R.sup.1 to R.sup.10 represents a group represented by formula (2):

OOR.sup.11X-A(2) and the others each independently represent a hydrogen atom, a halogen atom, a C.sub.1-4 alkyl group, or a C.sub.1-4 alkoxy group; R.sup.11 represents a C.sub.1-16 linear or branched alkylene group; X represents O or CONR.sup.21 (wherein R.sup.21 represents a hydrogen atom, or a C.sub.1-4 alkyl group; and A represents, for example, a group represented by formula (3)

##STR00002##

An object of the present invention is to develop a protecting group, which can prevent solidification or insolubilization of a compound by protecting a functional group to achieve easy separation and purification after a reaction.

A diphenylmethane compound represented by general formula (1):

##STR00001## wherein Y represents OR.sup.19 (wherein R.sup.19 represents a hydrogen atom or an active ester-type protecting group), NHR.sup.20 (wherein R.sup.20 represents, for example, a hydrogen atom, a C.sub.1-6 linear or branched alkyl group, or an aralkyl group, at least one of R.sup.1 to R.sup.10 represents a group represented by formula (2):

OOR.sup.11X-A(2) and the others each independently represent a hydrogen atom, a halogen atom, a C.sub.1-4 alkyl group, or a C.sub.1-4 alkoxy group; R.sup.11 represents a C.sub.1-16 linear or branched alkylene group; X represents O or CONR.sup.21 (wherein R.sup.21 represents a hydrogen atom, or a C.sub.1-4 alkyl group; and A represents, for example, a group represented by formula (3)

##STR00002##

The invention relates to a method for preparing an N-acyl- or N-sulfonyl--aminonitrile, comprising the following steps: a) condensation of an N-acyl- or N-sulfonyl--aminoaldehyde with hydroxylamine to give an aldoxime, and b) dehydration of the aldoxime obtained in step a) to give an N-acyl- or N-sulfonyl--aminonitrile. In an advantageous manner, the absolute configuration can be retained in the conversion to the N-acyl- or N-sulfonyl--aminonitrile.

The invention relates to a method for preparing an N-acyl- or N-sulfonyl--aminonitrile, comprising the following steps: a) condensation of an N-acyl- or N-sulfonyl--aminoaldehyde with hydroxylamine to give an aldoxime, and b) dehydration of the aldoxime obtained in step a) to give an N-acyl- or N-sulfonyl--aminonitrile. In an advantageous manner, the absolute configuration can be retained in the conversion to the N-acyl- or N-sulfonyl--aminonitrile.

Methods of synthesizing compounds using CO.sub.2 as a directing group for CH functionalization, and compounds made thereby, are described.

The present invention relates to an improved method for producing a diphenylmethane derivative which is effective as a sodium-dependent glucose cotransporter (SGLT) inhibitor, the method being carried out by means of a convergent synthesis method in which each major group is separately synthesized and then coupled. As such, in comparison to a linear synthesis method disclosed in existing documents, the synthesis pathway is compact and yield can be increased, and risk factors inherent in the linear synthesis pathway can be reduced. Furthermore, the crystal form of the compound produced according to the method has superb physicochemical characteristics, and thus can be effectively utilized in fields such as pharmaceutical manufacturing.