Patent TW-I235150-B (TW)
Title: Thio-oxindole derivates
Inventor: FENSOME ANDREW
IPC: C07D209/40
Filed: 2000-12-15
Granted: 2005-07-01
Abstract: This invention relates to a compound of the formula 1 or 2, wherein: R1 and R2 are chosen independently from the group of H, alkyl, substituted alkyl; OH; O (alkyl); O(substituted alkyl); OAc; aryl; optionally substituted aryl; heteroaryl; optionally substituted heteroaryl; alkylaryl; alkylheteroaryl; 1-propynyl; or 3-propynyl: or R1 and R2 are joined to form a ring comprising one of the following: -CH2(CH2)nCH2-; -CH2CH2CMe2CH2CH2-; -O(CH2)mCH2-; O(CH2)pO-; -CH2CH2OCH2CH2-; or -CH2CH2N(H or alkyl)CH2CH2-; m is an integer from 1 to 4; n is an integer from 1 to 5; p is an integer from 1 to 4; or R1 and R2 together comprise a double bond to one of the following: CMe2; C(cycloalkyl), 0, C(cyloether). R3 is selected from H, OH, NH2, C1 to C6 alkyl, substituted C1 to C6 alkyl, C3 to C6 alkenyl, alkynyl or substituted alkynyl, or CORA; RA is selected from H, C1 to C3 alkyl, substituted C1 to C3 alkyl, C1 to C3 alkoxy, substituted C1 to C3 alkoxy, C1 to C3 aminoalkyl, or substituted C1 to C3 aminoalkyl; R4 is selected from H, halogen, CN, NH2, C1 to C6 alkyl, substituted C1 to C6 alkyl, C1 to C6 alkoxy, substituted C1 to C6 alkoxy, C1 to C6 aminoalkyl, or substituted C1 to C6 aminoalkyl; R5 is selected from the groups (a), (b) or (c): (a) R5 is a trisubstituted benzene ring containing the substituents X, Y and Z as shown below: X is selected from halogen, OH, CN, C1 to C3 alkyl, substituted C1 to C3 alkyl, C1 to C3 alkoxy, substituted C1 to C3 alkoxy, C1 to C3 thioalkyl, substituted C1 to C3 thioalkyl, S(O)alkyl, S(O)2alkyl, C1 to C3 aminoalkyl, substituted C1 to C3 aminoalkyl, N02, C1 to C3 perfluoroalkyl, 5 or 6 membered heterocyclic ring containing 1 to 3 heteroatoms, CONH2, CSNH2, CONHalkyl, CSNHalkyl, CON(alkyl)2, CSN(alkyl)2, CORB, OCORB, NRCCORB; RB is selected from H, C1 to C3 alkyl, substituted C1 to C3 alkyl, aryl, substituted aryl, C1 to C3 alkoxy, substituted C1 to C3 alkoxy, C1 to C3 aminoalkyl, or substituted C1 to C3 aminoalkyl; RC is H, C1 to C3 alkyl, or substituted C1 to C3 alkyl; Y and Z are independently selected from H, halogen, CN, N02, C1 to C3 alkoxy, C1 to C3 alkyl, or C1 to C3 thioalkyl; or (b) R5 is a five or six membered heterocyclic ring with 1, 2, or 3 heteroatoms selected from O, S, SO, SO2 or NR6 and containing one or two independent substituents from the group of H, halogen, CN, NO2 and C1 to C3 alkyl, C1 to C3 alkoxy, C1 to C3 aminoalky1, CORD, or NRECORD; RD is H, C1 to C3 alkyl, substituted C1 to C3 alkyl, aryl, substituted aryl, C1 to C3 alkoxy, substituted C1 to C3 alkoxy, C1 to C3 aminoalkyl, or substituted C1 to C3 aminoalkyl; RE is H, C1 to C3 alkyl, or substituted C1 to C3 alkyl; R6 is H, or C1 to C3 alkyl; or (c) R5 is an indol-4-yl, indol-7-yl or benzo-2-thiophene moiety, the moiety being optionally substituted by from 1 to 3 substituents selected from halogen, lower alkyl, CN, NO2, lower alkoxy, or CF3; Q1 is S, NR7, CR8R9; R7 is selected from the group including CN, C1 to C6 alkyl, substituted C1 to C6 alkyl, C3 to C8 cycloalkyl, substituted C3 to C8 cycloalkyl, aryl. substituted aryl, heterocyclic, substituted heterocyclic, acyl substituted acyl, aroyl, substituted aroyl, SO2CF3, OR11 or NR11R12; R8 and R9 are independent substituents selected from the group of H, C1 to C6 alkyl, substituted C1 to C6 alkyl, C3 to C8 cycloalkyl, substituted C3 to C8 cycloalkyl, aryl, substituted aryl, heterocyclic, substituted heterocyclic, NO2, CN, or CO2R10, R10 is C1 to C3 alkyl; or CR8R9 comprises a six membered ring as shown by the structure below, Q2 is selected from the moieties: R11, R12 and R13 are independently selected from H, C1 to C6 alkyl, substituted C1 to C6 alkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, acyl, substituted acyl, aroyl or substituted aroyl or sulfonyl; or a pharmaceutically acceptable salt thereof; a pharmaceutical composition of such compounds and its use.