Derivatives of sulphonamides, their preparation and use as medicaments
AssigneeLaboratories Del Dr. Esteve, S.A.
InventorsRamon Merce-Vidal, Blas Andaluz-Mataro, Jordi Frigola-Constansa
Life of this patent
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Abstract
The present invention relates to new derivatives of sulphonamides, with the general formula (I), as well as to their physiologically acceptable salts, the processes for their preparation, their application as medicaments in human and/or veterinary therapy and the pharmaceutical compositions that contain them.
Claims6
A process for preparing a derivative of sulphonamide with the general formula (I)
- wherein
- A represents a substituent selected from among:
- A heteroaromatic ring of 5 or 6 members containing 1 or 2 heteroatoms selected from among oxygen, nitrogen and sulphur, optionally substituted by 1 or 2 halogen atoms, by a C1-C4 alkyl radical or by a phenyl radical or a heteroaryl radical with 5 or 6 members containing 1 or 2 atoms of oxygen, nitrogen or sulphur;
- A bicyclic heteroaromatic ring containing 1 to 3 heteroatoms selected from among oxygen, nitrogen and sulphur, optionally substituted by 1 or 2 halogen atoms or by a C1-C4 alkyl radical;
- A group selected from among:
- R1 represents hydrogen, a C1-C4 alkyl radical or a benzyl radical;
- n represents 0, 1, 2, 3 or 4;
- R2 represents —NR4R5 or a group with formula:
- wherein the dotted line represents an optional chemical bond;
- and
- R3, R4, and R5 independently represent hydrogen or a C1-C4 alkyl;
- X, Y and Z independently represent hydrogen, fluorine, chlorine, bromine, a C1-C4 alkyl, a C1-C4 alkoxy, a C1-C4 alkylthio, trifluoromethyl, cyano, nitro and —NR4R5;
- W represents a bond between the two rings, CH2, O, S and NR4;
- m represents 0, 1, 2, 3 or 4;
- with the condition that when m=0, A is a substituted phenyl;
- or one of its physiologically acceptable salts;
- said process comprising the steps of:
- reacting a compound with the general formula (II), or one of its suitably protected derivatives,
- wherein A is as indicated previously in the general formula (I), and X is a suitable leaving group including an halogen atom, particularly chlorine;
- with a 5-aminoindole with the general formula (III), or one of its suitably protected derivatives;
- wherein n, R1, R2 and R3 are as indicated above in the general formula (I);
- in order to obtain the corresponding sulphonamide, and optionally it is possible to remove eventually the protective groups from it.
A method for preventing or treating anxiety, depression, cognitive memory disorders and senile dementia processes and other dementias where a cognition deficit is predominant, psychosis, infantile hyperkinesia (ADHD, attention deficit/hyperactivity disorder) and other disorders mediated by the 5-HT6 receptor of serotonin in mammals, including man, comprising administering a therapeutically effective amount of a derivative of sulphonamide with the general formula (1),
- wherein
- A represents a substituent selected from among:
- A heteroaromatic ring of 5 or 6 members containing 1 or 2 heteroatoms selected from among oxygen, nitrogen and sulphur, optionally substituted by 1 or 2 halogen atoms, by a C1-C4 alkyl radical or by a phenyl radical or a heteroaryl radical with 5 or 6 members containing 1 or 2 atoms of oxygen, nitrogen or sulphur;
- A bicyclic heteroaromatic ring containing 1 to 3 heteroatoms selected from among oxygen, nitrogen and sulphur, optionally substituted by 1 or 2 halogen atoms or by a C1-C4 alkyl radical;
- A group selected from among:
- R1 represents hydrogen, a C1-C4 alkyl radical or a benzyl radical;
- n represents 0, 1, 2, 3 or 4;
- R2 represents —NR4R5 or a group with formula:
- wherein the dotted line represents an optional chemical bond;
- R3, R4 y R5 independently represent hydrogen or a C1-C4 alkyl;
- X, Y and Z independently represent hydrogen, fluorine, chlorine, bromine, a C1-C4 alkyl, a C1-C4 alkoxy, a C1-C4 alkylthio, trifluoromethyl, cyano, nitro and —NR4R5;
- W represents a bond between the two rings, CH2, O, S and NR4;
- m represents 0, 1, 2, 3 or 4;
- or one of its physiologically acceptable salts,
- to a mammal in need thereof.
Dependencies are inferred from the claim text.