New 4-amino-3-phenylamino-6-phenylpyrazolo(3,4-d)pyrimidine derivatives useful as a medicament for prophylactic- or therapeutic treatment of viral infections, preferably picornavirus infections and rhinovirus infections

摘要

4-Amino-3-phenylamino-6-phenylpyrazolo[3,4-d]pyrimidine derivatives (I), where at least one hydrogen atom in at least one of the phenyl groups A and B1, is replaced by a substituent R11 exhibiting a Hammett constant of greater than 0.23, and each further hydrogen atom in each phenyl groups A and B1, is optionally replaced by a group R1, are new. 4-Amino-3-phenylamino-6-phenylpyrazolo[3,4-d]pyrimidine derivatives of formula (I) or their salts or prodrugs, where at least one hydrogen atom in at least one of the phenyl groups A and B1, is replaced by a substituent R11 exhibiting a Hammett constant of greater than 0.23, and each further hydrogen atom in each of the phenyl groups A and B1, is optionally replaced by a group R1, are new. R1 : aliphatic group with 1-7 atoms or alkanol group with 1-8 atoms (both optionally saturated and optionally branched), halo, NO 2, CN, CON(R2) 2, COR2, COOR2, OR2, SR2, N(R2) 2, SO 2N(R2) 2, CX3, CR2(X) 2, OC(X) 3, OCR2(X) 2or phenyl; R2 : aliphatic group with 1-7 atoms (optionally saturated, optionally halogenated and optionally branched), mono- or poly-heterocyclyl (optionally saturated and contains N, S or O), H, benzyl, phenyl or naphthyl (all optionally substituted by F, Cl, Br, CF 3, alkyl, alkoxy, CN, NO 2, NH 2, aminoalkyl, C(O)-alkyl, C(O)O-alkyl, benzyl, phenyl or naphthyl); X : F, Cl, Br or I; and R11 : NO 2, CN, CF 3, CCl 3, CBr 3, OCF 3, OCCl 3, OCBr 3, CHF 2, CHCl 2, CHBr 2, OCHCl 2, CHO, COOH, COCH 3, COC 2H 5, COOCH 3or COOC 2H 5, preferably CF 3or OCF 3. Independent claims are also included for: (1) a pharmaceutical composition comprising (I); (2) preparing the pharmaceutical composition, comprising formulating (I) with a carrier; and (3) preparing (I). [Image] ACTIVITY : Virucide. The antiviral activity of (I) was tested against 20 clinical coxsackievirus b3 patient isolates. The results showed that 4-amino-3-(4-trifluoromethylphenyl)amino-6-phenylpyrazolo[3,4-d]pyrimidine exhibited mean IC50 value of 4.97+- 4.05 mu m. MECHANISM OF ACTION : None given.