HETEROCYCLIC COMPOUNDS SUITABLE FOR TREATING DISORDERS THAT RESPOND TO MODULATION OF THE SEROTONIN 5HT6 RECEPTOR
First Claim
Patent Images
1. A compound of the formula (I) whereinD is a group of the formula B or C n is or 2;
- G is CH2 or CHR3;
R1 is H, C1-C6-alkyl, C1-C6-alkyl substituted by C3-C6-cycloalkyl, C1-C6-hydroxyalkyl, fluorinated C1-C6-alkyl, C3-C6-cycloalkyl, fluorinated C3-C6-cycloalkyl, C3-C6-alkenyl, fluorinated C3-C6-alkenyl, formyl, acetyl, propionyl or benzyl;
R2, R2′
, R3, R4 and R4′
are, independently of each other, H, methyl, fluoromethyl, difluoromethyl, or trifluoromethyl;
A is 2,4-pyridylene, 3,5-pyridylene or 2,6-pyridylene, which is optionally substituted by one, two or three substituents selected from halogen, C1-C4-alkyl, C1-C4-alkoxy, fluorinated C1-C4-alkyl and fluorinated C1-C4-alkoxy;
E is NR7 or CH2, wherein R7 is H or C1-C3-alkyl;
Ar is a cyclic radical selected from the group consisting of phenyl, a 5- or 6-membered heteroaromatic radical comprising as ring members 1, 2 or 3 heteroatoms selected from N, O and S and a phenyl ring fused to a saturated or unsaturated 5- or 6-membered carbocyclic or heterocyclic ring, where the heterocyclic ring comprises as ring members 1, 2 or 3 heteroatoms selected from N, O and S and/or 1, 2 or 3 heteroatom-containing groups each independently selected from NR6, where R8 is H, C1-C4-alkyl, fluorinated C1-C4-alkyl, C1-C4-alkylcarbonyl or fluorinated C1-C4-alkylcarbonyl, and where the cyclic radical Ar may carry 1, 2 or 3 substituents Ra;
each R1 is independently halogen, hydroxyl, C1-C6-alkyl, fluorinated C1-C6-alkyl, C1-C6-hydroxyalkyl, C1-C6-alkoxy-C1-C6-alkyl, C2-C6-alkenyl, fluorinated C2-C6-alkenyl, C3-C6-cycloalkyl, fluorinated C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-hydroxyalkoxy, C1-C6-alkoxy-C1-C6-alkoxy, fluorinated C1-C6-alkoxy, C1-C6-alkylthio, fluorinated C1-C6-alkylthio, C1-C6-alkylsulfinyl, fluorinated C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, fluorinated C1-C6-alkylsulfonyl, phenylsulfonyl, pyridylsulfonyl, benzyloxy, phenoxy, phenyl, where the phenyl and the pyridyl radical in the 5 last-mentioned radicals may be unsubstituted or may carry 1 to 3 substituents selected from C1-C4-alkyl, fluorinated C1-C4-alkyl and halogen, CN, nitro, C1-C6-alkylcarbonyl, fluorinated C1-C6-alkylcarbonyl, C1-C6-alkylcarbonylamino, fluorinated C1-C6-alkylcarbonylamino, carboxy, NH—
C(O)—
NR6R7, NR6R7, NR6R7—
C1-C6-alkylene, O—
NR6R7, where R6 and R7 are, independently of each other, H, C1-C4-alkyl, fluorinated C1-C4-alkyl or C1-C4-alkoxy or may form, together with N, a 4-, 5- or 6-membered saturated or unsaturated ring, R10—
CO—
NR6—
C1-C6-alkylene, where R6 is as defined above and R10 is C1-C4-alkyl or phenyl, where the phenyl radical may be unsubstituted or may carry 1 to 3 substituents selected from C1-C4-alkyl, fluorinated C1-C4-alkyl and halogen, CH2-pyridyl, where the pyridyl radical may be unsubstituted or may carry 1 to 3 substituents selected from C1-C4-alkyl, fluorinated C1-C4-alkyl and halogen, or is a saturated or unsaturated aromatic or non-aromatic 3- to 7-membered heterocyclic ring comprising as ring members 1, 2, 3 or 4 heteroatoms selected from N, O and S and/or 1, 2 or 3 heteroatom-containing groups selected from NR9, where R9 has one of the meanings given for R8, SO, SO2 and CO, and where the heterocyclic ring may carry 1, 2 or 3 substituents selected from hydroxy, halogen, C1-C6-alkyl, fluorinated C1-C6-alkyl, C1-C6-alkoxy, fluorinated C1-C6-alkoxy, C1-C6-alkylthio, fluorinated C1-C6-alkylthio, NR6R7—
C1-C6-alkylene, where R6 and R7 are as defined above, carboxyl and C1-C4-alkoxycarbonyl;
and physiologically tolerated acid addition salts thereof.
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Accused Products
Abstract
The invention relates to compounds of the formula (I)
wherein the variables have meanings given in the claims and the description.
The invention also relates to the use of a compound of the formula I or a pharmaceutically acceptable salt thereof for preparing a medicament for the treatment of a medical disorder susceptible to the treatment with a 5HT6 receptor ligand.
4 Citations
38 Claims
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1. A compound of the formula (I)
wherein D is a group of the formula B or C n is or 2; -
G is CH2 or CHR3; R1 is H, C1-C6-alkyl, C1-C6-alkyl substituted by C3-C6-cycloalkyl, C1-C6-hydroxyalkyl, fluorinated C1-C6-alkyl, C3-C6-cycloalkyl, fluorinated C3-C6-cycloalkyl, C3-C6-alkenyl, fluorinated C3-C6-alkenyl, formyl, acetyl, propionyl or benzyl; R2, R2′
, R3, R4 and R4′
are, independently of each other, H, methyl, fluoromethyl, difluoromethyl, or trifluoromethyl;A is 2,4-pyridylene, 3,5-pyridylene or 2,6-pyridylene, which is optionally substituted by one, two or three substituents selected from halogen, C1-C4-alkyl, C1-C4-alkoxy, fluorinated C1-C4-alkyl and fluorinated C1-C4-alkoxy; E is NR7 or CH2, wherein R7 is H or C1-C3-alkyl; Ar is a cyclic radical selected from the group consisting of phenyl, a 5- or 6-membered heteroaromatic radical comprising as ring members 1, 2 or 3 heteroatoms selected from N, O and S and a phenyl ring fused to a saturated or unsaturated 5- or 6-membered carbocyclic or heterocyclic ring, where the heterocyclic ring comprises as ring members 1, 2 or 3 heteroatoms selected from N, O and S and/or 1, 2 or 3 heteroatom-containing groups each independently selected from NR6, where R8 is H, C1-C4-alkyl, fluorinated C1-C4-alkyl, C1-C4-alkylcarbonyl or fluorinated C1-C4-alkylcarbonyl, and where the cyclic radical Ar may carry 1, 2 or 3 substituents Ra; each R1 is independently halogen, hydroxyl, C1-C6-alkyl, fluorinated C1-C6-alkyl, C1-C6-hydroxyalkyl, C1-C6-alkoxy-C1-C6-alkyl, C2-C6-alkenyl, fluorinated C2-C6-alkenyl, C3-C6-cycloalkyl, fluorinated C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-hydroxyalkoxy, C1-C6-alkoxy-C1-C6-alkoxy, fluorinated C1-C6-alkoxy, C1-C6-alkylthio, fluorinated C1-C6-alkylthio, C1-C6-alkylsulfinyl, fluorinated C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, fluorinated C1-C6-alkylsulfonyl, phenylsulfonyl, pyridylsulfonyl, benzyloxy, phenoxy, phenyl, where the phenyl and the pyridyl radical in the 5 last-mentioned radicals may be unsubstituted or may carry 1 to 3 substituents selected from C1-C4-alkyl, fluorinated C1-C4-alkyl and halogen, CN, nitro, C1-C6-alkylcarbonyl, fluorinated C1-C6-alkylcarbonyl, C1-C6-alkylcarbonylamino, fluorinated C1-C6-alkylcarbonylamino, carboxy, NH—
C(O)—
NR6R7, NR6R7, NR6R7—
C1-C6-alkylene, O—
NR6R7, where R6 and R7 are, independently of each other, H, C1-C4-alkyl, fluorinated C1-C4-alkyl or C1-C4-alkoxy or may form, together with N, a 4-, 5- or 6-membered saturated or unsaturated ring, R10—
CO—
NR6—
C1-C6-alkylene, where R6 is as defined above and R10 is C1-C4-alkyl or phenyl, where the phenyl radical may be unsubstituted or may carry 1 to 3 substituents selected from C1-C4-alkyl, fluorinated C1-C4-alkyl and halogen, CH2-pyridyl, where the pyridyl radical may be unsubstituted or may carry 1 to 3 substituents selected from C1-C4-alkyl, fluorinated C1-C4-alkyl and halogen, or is a saturated or unsaturated aromatic or non-aromatic 3- to 7-membered heterocyclic ring comprising as ring members 1, 2, 3 or 4 heteroatoms selected from N, O and S and/or 1, 2 or 3 heteroatom-containing groups selected from NR9, where R9 has one of the meanings given for R8, SO, SO2 and CO, and where the heterocyclic ring may carry 1, 2 or 3 substituents selected from hydroxy, halogen, C1-C6-alkyl, fluorinated C1-C6-alkyl, C1-C6-alkoxy, fluorinated C1-C6-alkoxy, C1-C6-alkylthio, fluorinated C1-C6-alkylthio, NR6R7—
C1-C6-alkylene, where R6 and R7 are as defined above, carboxyl and C1-C4-alkoxycarbonyl;and physiologically tolerated acid addition salts thereof. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38)
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Specification