Substituted indanyl sulfonamide compounds, their preparation and use as medicaments
AssigneeLaboratorios Del Dr. Esteve, S.A.
InventorsMaria De Las Ermitas Alcalde-Pais, Maria De Les Neus Mesquida-Estevez, Sara Lopez-Perez, Jordi Frigola-Constansa, Joerg Holenz, Ramon Merce-Vidal
Life of this patent
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Abstract
The present invention refers to new indanyl sulphonamide compounds with general formula (I), as well as to their preparation procedure, their application as medicine and the pharmaceuticals composition which they are made up of. The new compounds of formula I show affinity for 5-HT6 receptors and are, therefore, effective for treating diseases mediated by these receptors.
Claims13
A substituted indanyl sulfonamide compound of general formula I,
- wherein
- R1, R2, R3, R4, independent from one another, each represent an hydrogen atom;
- or a linear or branched, saturated or unsaturated C1-5 aliphatic radical which may be substituted with 1, 2 or 3 substituent(s) independently selected from the group consisting of F, Cl, Br, —OH, —NH2, —SH, —O—CH3, —O—C2H5, —NO2, —CN, —NH—CH3 and —S—CH3;
- R5, R6, R7 and R8, independent from one another, each represent a hydrogen atom;
- —NO2;
- —NH2;
- —SH;
- —OH;
- —CN;
- —C(═O)—H;
- —C(═O)—R10;
- —OR11;
- —SR12;
- —S(═O)2—N(R14)R15, —N(R16)—S(═O)2—R17;
- —NH—R18;
- —NR19R20;
- F;
- Cl, Br;
- I;
- a linear or branched, saturated or unsaturated C1-6 aliphatic radical which may be substituted with 1, 2 or 3 substituent(s) independently selected from the group consisting of F, Cl, Br, —OH, —NH2, —SH, —O—CH3, —O—C2H5, —NO2, —CN, —NH—CH3 and —S—CH3;
- or a 5- to 14-membered aryl or heteroaryl radical, which may be substituted with 1, 2 or 3 substituent(s) independently selected from the group consisting of —CF3, C1-5-alkyl, —O—C1-5-alkyl, —S—C1-5-alkyl, —C(═O)—OH, —C(═O)—O—C1-5-alkyl, —O—C(═O)—C1-5-alkyl, F, Cl, Br, I, —CN, —OCF3, —SCF3, —OH, —SH, —NH(C1-5-alkyl), —N(C1-5-alkyl)2, —NH—C(═O)—C1-5-alkyl, —N(C1-5-alkyl)-C(═O)—C1-5-alkyl, —NO2, —CHO, —CF2H, —CFH2, —C(═O)—NH2, —C(═O)—NH(C1-5-alkyl), —C(═O)—N(C1-5-alkyl)2, —S(═O)2—C1-5-alkyl, —S(═O)2-phenyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, phenoxy and benzyl and which may be bonded via a linear or branched C1-6 alkylene group and wherein the heteroaryl radical contains 1, 2 or 3 heteroatom(s) independently selected from the group consisting of nitrogen, oxygen and sulfur as ring member(s);
- with the condition that at least one of the substituents R5, R6, R7 and R8 represents a —S(═O)2—N(R14)R15 or a —N(R16)—S(═O)2—R17 radical;
- A represents
- which means (Ib) type compounds:
- wherein
- X represents NH, O or S
- R23 represents NH2 or NH—NH2
- R10 to R12 and R14 to R20, independent from one another, each represent a hydrogen atom;
- a linear or branched, saturated or unsaturated C1-5 aliphatic radical which may be substituted with 1, 2 or 3 substituent(s) independently selected from the group consisting of F, Cl, Br, —OH, —NH2, —SH, —O—CH3, —O—C2H5, —NO2, —CN, —NH—CH3 and —S—CH3;
- a saturated or unsaturated 3 to 8-membered cycloaliphatic radical, which may be substituted with 1, 2 or 3 substituent(s) independently selected from the group consisting of C1-5-alkyl, —O—C1-5-alkyl, —S—C1-5-alkyl, oxo (═O), thioxo (═S), —C(═O)—OH, —C(═O)—O—C1-5-alkyl, —O—C(═O)—C1-5-alkyl, F, Cl, Br, I, —CN, —CF3, —OCF3, —SCF3, —OH, —SH, —NH2, —NH(C1-5-alkyl), —N(C1-5-alkyl)2, —NO2, —CHO, —CF2H, —CFH2, —C(═O)—NH2, —C(═O)—NH(C1-5-alkyl), —C(═O)—N(C1-5-alkyl)2, —S(═O)2—C1-5-alkyl, —S(═O)2-phenyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, phenoxy and benzyl and which may optionally contain 1, 2 or 3 heteroatom(s) independently selected from the group consisting of nitrogen, oxygen and sulfur as ring member(s) and which may be bonded via a linear or branched C1-6 alkylene group;
- or a 5- to 14-membered aryl or heteroaryl radical, which may be substituted with 1, 2 or 3 substituent(s) independently selected from the group consisting of —CF3, C1-5-alkyl, —S—C1-5-alkyl, —C(═O)—OH, —C(═O)—O—C1-5-alkyl, —O—C(═O)—C1-5-alkyl, F, Cl, Br, I, —CN, —OCF3, —SCF3, —OH, —SH, —NH2, —NH(C1-5-alkyl), —N(C1-5-alkyl)2, —NH—C(═O)—C1-5-alkyl, —N(C1-5-alkyl)-C(═O)—C1-5-alkyl, NO2, —CHO, —CF2H, —CFH2, —C(═O)—NH2, —C(═O)—NH(C1-5-alkyl), —C(═O)—N(C1-5-alkyl)2, —S(═O)2—C1-5-alkyl, —S(═O)2-phenyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, phenoxy and benzyl and which may be bonded via a linear or branched C1-6 alkylene, C2-6 alkenylene or C2-6 alkinylene group and wherein the heteroaryl radical contains 1, 2 or 3 heteroatom(s) independently selected from the group consisting of nitrogen, oxygen and sulfur as ring member(s);
- or a pharmaceutically acceptable salt thereof optionally in form of one of its stereoisomers, a racemate or in form of a mixture of at least two of its stereoisomers, in any mixing ratio, or a physiologically acceptable salt thereof.
A substituted indanyl sulfonamide compound of general formula I,
- wherein
- R1, R2, R3, R4, K independent from one another, each represent an hydrogen atom;
- or a linear or branched, saturated or unsaturated C1-5 aliphatic radical which may be substituted with 1, 2 or 3 substituent(s) independently selected from the group consisting of F, Cl, Br, —OH, —NH2, —SH, —O—CH3, —O—C2H5, —NO2, —CN, —NH—CH3 and —S—CH3;
- R5, R6, R7 and R8, independent from one another, each represent a hydrogen atom;
- —NO2;
- —NH2;
- —SH;
- —OH;
- —CN;
- —C(═O)—H;
- —C(═O)—R10;
- —OR11;
- —SR12;
- —S(═O)2—N(R14)R15;
- —N(R16)—S(═O)2—R17;
- —NH—R18;
- —NR19R20;
- F;
- Cl, Br;
- I;
- a linear or branched, saturated or unsaturated C1-6 aliphatic radical which may be substituted with 1, 2 or 3 substituent(s) independently selected from the group consisting of F, Cl, Br, —OH, —NH2, —SH, —O—CH3, —O—C2H5, —NO2, —CN, —NH—CH3 and —S—CH3;
- or a 5- to 14-membered aryl or heteroaryl radical, which may be substituted with 1, 2 or 3 substituent(s) independently selected from the group consisting of —CF3, C1-5-alkyl, —O—C1-5-alkyl, —S—C1-5-alkyl, —C(═O)—OH, —C(═O)—O—C1-5-alkyl, —O—C(═O)—C1-5-alkyl, F, Cl, Br, I, —CN, —OCF3, —SCF3, —OH, —SH, —NH2, —NH(C1-5-alkyl), —N(C1-5-alkyl)2, —NH—C(═O)—C1-5-alkyl, —N(C1-5-alkyl)-C(═O)—C1-5-alkyl, —NO2, —CHO, —CF2H, —CFH2, —C(═O)—NH2, —C(═O)—NH(C1-5-alkyl), —C(═O)—N(C1-5-alkyl)2, —S(═O)2—C1-5-alkyl, —S(═O)2-phenyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, phenoxy and benzyl and which may be bonded via a linear or branched C1-6 alkylene group and wherein the heteroaryl radical contains 1, 2 or 3 heteroatom(s) independently selected from the group consisting of nitrogen, oxygen and sulfur as ring member(s);
- with the condition that at least one of the substituents R5, R6, R7 and R8 represents a —S(═O)2—N(R14)R15 or a —N(R16)—S(═O)2—R17 radical;
- A represents
- which means (Ib) type compounds:
- wherein
- X represents NH, O or S
- R23 represents NH2 or NH—NH2
- R10 to R12 and R14 to R20, independent from one another, each represent a hydrogen atom;
- a linear or branched, saturated or unsaturated C1-5 aliphatic radical which may be substituted with 1, 2 or 3 substituent(s) independently selected from the group consisting of F, Cl, Br, —OH, —NH2, —SH, —O—CH3, —O—C2H5, —NO2, —CN, —NH—CH3 and —S—CH3;
- a saturated or unsaturated 3 to 8-membered cycloaliphatic radical, which may be substituted with 1, 2 or 3 substituent(s) independently selected from the group consisting of C1-5-alkyl, —O—C1-5-alkyl, oxo (═O), thioxo (═S), —C(═O)—OH, —C(═O)—O—C1-5-alkyl, —O—C(═O)—C1-5-alkyl, F, Cl, Br, I, —CN, —CF3, —OCF3, —SCF3, —OH, —SH, —NH2, —NH(C1-5-alkyl), —N(C1-5-alkyl)2, —NO2, —CHO, —CF2H, —CFH2, —C(═O)—NH2, —C(═O)—NH(C1-5-alkyl), —C(═O)—N(C1-5-alkyl)2, —S(═O)2—C1-5-alkyl, —S(═O)2-phenyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, phenoxy and benzyl and which may optionally contain 1, 2 or 3 heteroatom(s) independently selected from the group consisting of nitrogen, oxygen and sulfur as ring member(s) and which may be bonded via a linear or branched C1-6 alkylene group;
- or a 5- to 14-membered aryl or heteroaryl radical, which may be substituted with 1, 2 or 3 substituent(s) independently selected from the group consisting of —CF3, C1-5-alkyl, —O—C1-5-alkyl, —S—C1-5-alkyl, —C(═O)—OH, —C(═O)—O—C1-5-alkyl, —O—C(═O)—C1-5-alkyl, F, Cl, Br, I, —CN, —OCF3, —SCF3, —OH, —SH, —NH2, —NH(C1-5-alkyl), —N(C1-5-alkyl)2, —NH—C(═O)—C1-5-alkyl, —N(C1-5-alkyl)-C(═O)—C1-5-alkyl, —NO2, —CHO, —CF2H, —CFH2, —C(═O)—NH2, —C(═O)—NH(C1-5-alkyl), —C(═O)—N(C1-5-alkyl)2, —S(═O)2—C1-5-alkyl, —S(═O)2-phenyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, phenoxy and benzyl and which may be bonded via a linear or branched C1-6 alkylene, C2-6 alkenylene or C2-6 alkinylene group and wherein the heteroaryl radical contains 1, 2 or 3 heteroatom(s) independently selected from the group consisting of nitrogen, oxygen and sulfur as ring member(s);
- or a pharmaceutically acceptable salt thereof optionally in form of one of its stereoisomers, a racemate or in form of a mixture of at least two of its stereoisomers, in any mixing ratio, or a physiologically acceptable salt thereof.
Dependencies are inferred from the claim text.