New C-glycoside derivatives useful to prevent and/or treat cutaneous autoimmune diseases e.g. psoriasis, vitiligo and alopecia, cutaneous atopic disorders e.g. atopic eczema, and adverse effects of UV-radiation and itching

摘要

#CMT# #/CMT# C-glycoside derivatives (I), are new. #CMT# : #/CMT# C-glycoside derivatives of formula (I), are new. X : -CO-, -CH(NR1R2)-, -CHR1- (all preferred) or -C(=CHR2)-; R : 1-14C (cyclo)alkyl, 1-14C (cyclo)perfluoroalkyl, 1-14C (cyclo)hydrofluoroalkyl (all optionally interrupted by O, S, N or Si, and substituted by OR1a, -SR1b, -NR1cR2a, -COOR2b, -CONHR2c, CN, halo, perfluoroalkyl, hydrofluoroalkyl and/or cycloalkyl, aryl or optionally substituted heterocyclyl) or phenyl, preferably 1-10C alkyl or phenyl; R1, R1, R2H or OH; R2 : R or OH; R2a, R2c : H or T; T : 1-14C alkyl, OH, 1-14C perfluoroalkyl and/or 1-14C hydrofluoroalkyl; and R1a, R1b, R2b, R1c : T, provided that: (1) R1 and R2 are not hydroxyl group simultaneously; (2) R2a and R1c are not hydroxyl group simultaneously; (3) X and R are not phenyl group simultaneously, and (4) the following compounds are excluded: 1-(C-beta -D-galactopyranosyl)-2-hydroxyl-propane, 1-(C-alpha -D-galactopyranosyl)-2-hydroxyl-propane, 1-(C-beta -D-galactopyranosyl)-propane-2-one, 1-(C-alpha -D-galactopyranosyl)-propane-2-one, 1-(C-beta -D-galactopyranosyl)-2-amino-propane, 1-(C-alpha -D-galactopyranosyl)-2-amino-propane, 1-(C-beta -D-galactopyranosyl)-2-phenylamino-propane, 1-(C-alpha -D-galactopyranosyl)-2-phenylamino-propane, 3-methyl-4-(beta -D-galactopyranosyl)-butyric acid ethyl ester, 3-methyl-4-(alpha -D-galactopyranosyl)-butyric acid ethyl ester, 1-(C-beta -D-galactopyranosyl)-hexane-2,6-diol, 1-(C-alpha -D-galactopyranosyl)-hexane-2,6-diol and 1-phenyl-2-(C-beta -D-galactopyranosyl)-ethane-1-one. An independent claim is included for a composition comprising (I). #CMT#[Image]#/CMT# #CMT#ACTIVITY : #/CMT# Dermatological; Antipsoriatic; Antiinflammatory; Immunosuppressive; Endocrine-Gen; Antiinflammatory. #CMT#MECHANISM OF ACTION : #/CMT# None given. #CMT#USE : #/CMT# (I) are useful to prepare the composition to prevent and/or treat cutaneous autoimmune diseases (e.g. delayed-hypersensitivity contact reactions, psoriasis, vitiligo, diffuse scleroderma, lupus erythematosus and alopecia) and cutaneous atopic disorders (e.g. cutaneous allergic reactions, atopic dermatitis and atopic eczema); and to treat, prevent and/or reduce the adverse effects of UV-radiation and itching (claimed). The immunostimulating activity of 1-(C-beta -D-lactopyranosyl)propane-2-one was tested in human. The result showed that 1-(C-beta -D-lactopyranosyl)propane-2-one had an activation concentration of 0.05 mM. #CMT#ADVANTAGE : #/CMT# (I) fight against weakening of natural defenses of the skin (i.e. due to chronological and photo-inducible aging) and/or strengthen natural defenses of the skin (claimed). #CMT#ORGANIC CHEMISTRY : #/CMT# Preparation (Disclosed): Preparation of (I) is carried out using the method described in . #CMT#PHARMACEUTICALS : #/CMT# Preferred Composition: The composition further comprises a capillary agent. #CMT#ADMINISTRATION : #/CMT# Administration of (I) is topical on skin, mucous membranes or scalp (claimed). #CMT#SPECIFIC COMPOUNDS : #/CMT# 6 Compounds (I) are specifically claimed e.g. 1-(C-beta -D-galactopyranosyl)-propan-2-one (Ia), phenyl-2-(C-alpha -D-galactopyranosyl)-1-hydroxy-ethane, 1-(C-beta -D-galactopyranosyl)-undecan-2-one, 1-(2-(3-hydroxypropylamino)-propyl)-C-alpha -D-galactopyranose and, 3-methyl-4-(C-beta -D-galactopyranosyl)-2-butyric acid ethyl ester. #CMT#EXAMPLE : #/CMT# No suitable example given.