Patent NZ-337331-A (NZ)
Title: Aryl-sulfonamides and analogues thereof and their use in the treatment of neurodegenerative diseases
Inventor: MITTENDORF JOACHIM
IPC: C07D209/44
Filed: 1998-02-10
Abstract: Compounds of the general formula:  R1 -A -D -E -G -L -R2 wherein: R1 represents naphthyl, isoquinolyl or a radical of formulae (II) in which a is 1 or 2, R3 is hydrogen, alkenyl, alkyl or acyl, and where all the abovementioned ring systems and radicals are optionally substituted, if appropriate geminally, by one or more, identical or different substituents which are selected from the group which consists of halogen, carboxyl, hydroxyl, phenyl, aIkoxy, aIkoxycarbonyl, alkyl, which, for its part, can be substituted by halogen, alkylsulphonyloxy, azide, amino, mono- or di-alkylamino or hydroxy; a group of the formula -(CO)b-NR4R5, in which b is 0 or 1, R4 and R5 are identical or different and independently of one another are hydrogen, phenyl, acyl, cycloacyl, benzoyl or alkyl which is optionally substituted by amino, mono- or di-alkylamino, or R4 and R5, together with the nitrogen atom, form a 5- or 6-membered saturated heterocycle which can optionally contain one or more further heteroatoms from the group consisting of S and 0 and/or one or more radicals of the formula -NR8, wherein R8 is hydrogen, alkyl or acyl; or a group of the formula -NR6-SO2-R7 in which R6 is hydrogen, phenyl, alkyl or acyl and R7 is phenyl or alkyl; A and E are identical or different and represent a bond or alkylene; D represents an oxygen atom or a radical of the formula -S(O)c- or -N(R9)- in which c is 0, 1 or 2 and R9 is hydrogen, alkyl or acyl; G represents doubly bonded aryl or a doubly bonded 5- to 7-membered aromatic heterocycle having up to 3 heteroatoms from the group consisting of S, N and/or O, each of which is optionally substituted by one or more, identical or different substituents which are selected from the group which consists of hydroxyl, trifluoromethyl, carboxyl, halogen, alkyl, hydroxyalkyl, alkoxy, alkoxycarbonyl, -CO-O-(CH2)d-NR10R11, -NR12-SO2R13, -(CH2)e-(CO)fNR14R15 and -OR16 in which: d is 1, 2, 3 or 4: e and f are each independently 0 or 1; R10 and R11 have the meaning of R4 and R5; R12 has the meaning of R6; R13 has the meaning of R7; R14 and R15 have the meaning of R4 and R5 or independently of one another represent a radical of the formula -(CH2)g-NR17R18 in which g is a number 1, 2, 3 or 4, and R17 and R18 have the meaning of R4 and R5; R16 is aryl; L represents a radical of formula (III) where the bonding of the radicals to G takes place at the left bond, and in which R19, R20, R21, R22, R23, R24, R25, R26 and R27 are identical or different and are hydrogen or alkyl, or R19 is a radical of the formula -SO2R2; R2 represents: a radical of formula (IV), morpholine, cycloalkyl, aryl or a 5- to 7-membered saturated or aromatic heterocycle having up to 3 heteroatoms from the group consisting of S, N and/or O, each of which is optionally substituted by one or more, identical or different substituents which are selected from the group of halogen, trifluoromethyl, nitro, amino and alkyl; alkyl, alkenyl or alkynyl, each of which is optionally substituted by one or more, identical or different substituents which are selected from the group of halogen, trifluoromethyl, hydroxyl, cyano, azido, alkoxy, perfluoroalkoxy, partially fluorinated alkoxy, a radical of formula (V), -NR28R29, in which R28 and R29 have the meaning of R4 and R5; phenyl, optionally substituted by one or more, identical or different substituents which are selected from the group of halogen, nitro, hydroxyl, alkyl, alkoxy and a group of the formula -NR30R31, in which R30 and R31 are identical or different and are hydrogen or alkyl or acyl, and a 5- to 6-membered aromatic heterocycle having up to three heteroatoms from the group consisting of S, N and/or O, optionally substituted by one or more, identical or different substituents which are selected from the group of halogen, nitro, hydroxyl, alkyl, alkoxy and a group of the formula -NR30R31, in which R30 and R31 are as defined above, or L and R2 together represent a radical of formula (VI) and their salts, with the exception of m-bis (l-naphthyloxy) benzene. The compounds are useful in the prevention and/or treatment of cerebral ischaemias and craniocerebral trauma, the treatment of states of pain, emesis, nausea, glaucoma, asthma, anorexia, convulsions, rheumatism, sedation and mobility disorders, the treatment of bacterial or viral infections, autoimmune diseases, inflammatory or auto immunologically related diseases of the joints of the bone and muscle apparatus, of the internal and external organs, of the central nervous system, of the sense organs and of the haematogenic system in humans and animals.