New unsaturated fatty amino acid derivatives useful e.g. to prepare dermocosmetologic antiradical, anti-inflammatory, anti-pruritic or anticollagenase compositions and to treat skin aging, keratinization and pigmentation disorders

摘要

Unsaturated fatty amino acid derivatives (I) and their acid addition salts, as drugs, are new. Unsaturated fatty amino acid derivatives of formula (R a)(R b)N-CH 2-(CH(R n)) n-CH=C(R 1)-C(O)-OR (I) and their acid addition salts, as drugs, are new. X : O or NH; R nH or 1-6C alkyl (optionally substituted by halo), preferably H; R 1H, F, Cl or Br, CF 3, CHF 2 or 1-6C alkyl, 1-6C alkenyl or 1-6C alkynyl (optionally substituted by halo), preferably H or F; R : H, 1-6C alkyl or 3-6C cycloalkyl (optionally substituted by halo), preferably H; R a, R bH, 1-6C alkyl or 1-6C acyl, preferably H, or 4-6C hydrocarbon ring; and n : 2-14, preferably 3. Provided that as a new compound (I) is excluded from 6-amino-hex-2-enoic acid, its hydrochloride and trifluoroacetate, 8-amino-oct-2-enoic acid trifluoroacetate, 8-(dimethylamino)-oct-2-enoic acid, 12-(dimethylamino)-dodec-2-enoic acid, 6-(isopropylamino)-2-methyl-hex-2-enoate, ethyl-6-(tert-butylamino)-2-methyl-hex-2-enoate, 6-amino-2-methyl-hex-2-enoate, 7-amino-hept-2-enoate, 7-amino-2-methyl-hept-2-enoate and 7-amino-4-methyl-hept-2-enoate. Independent claims are included for: (1) the preparation of (I); and (2) an ester compound of formula PG-N(R d)-CH 2-(CHR 1)-C(O)-OR c (VIII). R cH or 1-6C alkyl; R 1H, F, Cl, Br, -CF 3 or -CHF 2, or 1-6C alkyl, alkenyl or alkynyl (optionally substituted by halo, preferably F); PG : a protecting group forming a carbamate group, preferably tert. butyl carbamate or benzyl carbamate, and R dH or PG, provided that (VIII) is excluded from tert-butyl-(E)-6-(N,N-di-tert-butoxycarbonylamino)-hex-2-tert-enoate, ethyl (E)-6-(N-tert-butoxy-carbonylamino)-hex-2-enoate, methyl-(E)-7-(E-tert-butoxy-carbonylamino)-hept-2-enoate and (E)-7-(E-tert-butoxy-carbonylamino)-hept-2-enoic acid. ACTIVITY : Dermatological; Antiinflammatory; Antipruritic; Vulnerary. MECHANISM OF ACTION : Melanogenesis modulator.