N-[(Piperazinyl)hetaryl]arylsulfonamide compounds
Abstract
The invention relates to N-[(piperazinyl)hetaryl]arylsulfonamide compounds of the general formula I in which Q is a bivalent, 6-membered heteroaromatic radical which possesses 1 or 2 N atoms as ring members and which optionally carries one or two substituents R a which is/are selected, independently of each other, from halogen, CN, NO 2 , CO 2 R 4 , COR 5 , C 1 -C 4 -alkyl and C 1 -C 4 -haloalkyl; Ar is phenyl or a 6-membered heteroaromatic radical which possesses 1 or 2 N atoms as ring members and which optionally carries one or two substituents R b , which is/are selected from halogen, NO 2 , CN, CO 2 R 4 , COR 5 , C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl and C 1 -C 4 -haloalkyl, with it also being possible for two radicals R b which are bonded to adjacent C atoms of Ar to be together C 3 -C 4 -alkylene; R 1 is hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -hydroxyalkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 4 -alkenyl or C 3 -C 4 -alkynyl; with the radicals n, R 1 , R 2 , R 3 , R 4 and R 5 having the meanings given in the patent claims, to the N-oxides and to the physiologically tolerated acid addition salts of these compounds and to pharmaceutical compositions which comprise at least one N-[(piperazinyl)hetaryl]arylsulfonamide compound as claimed in one of claims 1 to 10 and/or at least one physiologically tolerated acid addition salt of I and/or an N-oxide of I, where appropraite together with physiologically accpetable carriers and/or auxiliary substances for treating diseases which respond to influencing by dopamine D 3 receptor antagonists or agonists, in particular for treating diseases of the central nervous system and disturbances of kidney function.
Claims
exact text as granted — not AI-modified1 . An N-[(piperazinyl)hetaryl]arylsulfonamide compound of the general formula I
in which
Q is a bivalent, 6-membered heteroaromatic radical which possesses 1 or 2 N atoms as ring members and which optionally carries one or two substituents R a which is/are selected, independently of each other, from halogen, CN, NO 2 , CO 2 R 4 , COR 5 , C 1 -C 4 -alkyl and C 1 -C 4 -haloalkyl;
Ar is phenyl or a 6-membered heteroaromatic radical which possesses 1 or 2 N atoms as ring members and which optionally carries one or two substituents R b , which is/are selected from halogen, NO 2 , CN, CO 2 R 4 , COR 5 , C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl and C 1 -C 4 -haloalkyl, with it also being possible for two radicals R which are bonded to adjacent C atoms of Ar to be together C 3 -C 4 -alkylene;
n is 0, 1 or 2;
R 1 is hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, C 1 -C 4 -hydroxyalkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 4 -alkenyl or C 3 -C 4 -alkynyl;
R 2 is C 1 -C 4 -alkyl or, together with R 1 , is C 2 -C 5 -alkylene or, in the case of n=2, the two radicals R 2 can together be C 1 -C 4 -alkylene;
R 3 is hydrogen or C 1 -C 4 -alkyl;
R 4 is C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 2 -C 4 -alkenyl C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, phenyl or benzyl; and
R 5 is hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 2 -C 4 -alkenyl C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, phenyl or benzyl;
the N-oxides thereof and the physiologically tolerated acid addition salts of these compounds;
with the exception of the compounds: 4-methyl-N-[6-(4-methylpiperazin-1-yl)pyridin-3-yl)benzenesulfonamide and 4-chloro-N-[6-(4-methylpiperazin-1-yl)pyridin-3-yl)benzenesulfonamide.
2 . The compound as claimed in claim 1 , in which the piperazine ring is bonded to the heteroaromatic radical 0 in the para position in relation to the group N(R 3 )—SO 2 —Ar.
3 . The compound as claimed in one of the preceding claims, in which Q is a radical of the formula
in which A 1 , A 2 and A 3 are, independently of each other, N or CH, one or two of the variables A 1 , A 2 and A 3 can also be C—R a , k=0 or 1 and R a is selected from halogen, C 1 -C 4 -alkyl and C 1 -C 4 -haloalkyl, with A 1 , A 2 and A 3 not simultaneously being N or simultaneously being selected from CH and C—R a .
4 . The compound as claimed in claim 3 , in which Q is pyridin-2,5-diyl which carries the piperazine radical in the 2 position.
5 . The compound as claimed in one of the preceding claims, in which the radical Ar carries a substituent R b in the para position and, where appropriate, a further substituent R b in the meta position or in the ortho position, in each case based on the binding site of the sulfonamide group.
6 . The compound as claimed in one of the preceding claims, in which Ar is phenyl or pyridyl, which radicals possess, where appropriate, one or 2 R b substituents.
7 . The compound as claimed in one of the preceding claims, in which R 1 is different from hydrogen and methyl.
8 . The compound as claimed in claim 1 of the general formula Ia
in which n, R 1 , R 2 , R 3 , R a and R b have the meanings given in claim 1 and in which either A 1 , A 2 and A 3 are, independently of each other, N or CH and one or two of the variables A 1 , A 2 and A 3 can also be C—R a , with A 1 , A 2 and A 3 not simultaneously being N or simultaneously being selected from CH and C—R a ,
X and Y are selected from CH, C—R b′ and N, in which R b′ is halogen, methyl, CN, difluoromethyl or trifluoromethyl, with X and Y not simultaneously being N or simultaneously being C—R b′ , and
k is 0 or 1.
9 . The compound as claimed in claim 8 of the general formula Ia.1
in which n, X, Y, R 1 , R 2 , R 3 , R a and R b have the meanings given in claim 8 and q is 0, 1 or 2.
10 . The compound as claimed in claim 8 of the general formula Ia.2
in which n, X, Y, R 1 , R 2 , R 3 , R a and R b have the meanings given in claim 8 and q is 0, 1 or 2.
11 . The compound as claimed in claim 8 , in which k=0, with A 1 , A 2 and A 3 being, independently of each other, N or CH and A 1 , A 2 and A 3 not simultaneously being N or simultaneously being CH.
12 . The compound as claimed in one of claims 8 to 11 , in which n is 0 or 1 and, in the case of n=1, R 2 is bonded to the C atom of the piperazine ring which is adjacent to the group R 1 =N and is a methyl group having the S configuration.
13 . A pharmaceutical composition which comprises at least one N-[(piperazinyl)hetaryl]arylsulfonamide compound as claimed in one of claims 1 to 10 and/or at least one physiologically tolerated acid addition salt of I and/or an N-oxide of I, where appropriate together with physiologically acceptable carriers and/or auxiliary substances.
14 . The use of at least one N-[(piperazinyl)hetaryl]arylsulfonamide compound of the formula I
in which Q, Ar, n, R 1 , R 2 and R 3 have the previously mentioned meanings, of the N-oxides thereof and of the physiologically tolerated acid addition salts thereof for producing a pharmaceutical composition for treating diseases which respond to influencing by dopamine D 3 receptor antagonists or dopamine D 3 agonists.
15 . The use as claimed in claim 14 for treating diseases of the central nervous system.
16 . The use as claimed in claim 14 for treating kidney function disturbances.Join the waitlist — get patent alerts
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