Back to results
US 2001/0020095 A1Published application
Indane or dihydroindole derivatives
AssigneeH. Lundbeck A/S
InventorsJens Kristian Perregaard, Benny Bang-Andersen, Henrik Pedersen, Ivan Mikkelsen, Robert Dancer
Life of this patent
Estimating the term…
Abstract
The present invention relates to substituted indane or dihydroindole compounds of Formula (I) 1 wherein A is an indole. These compounds have high affinity for D4 receptors.
Claims59
A substituted indane or dihydroindole compound of Formula I 14
- wherein A is a group 15
- Y is a hydrocarbon group completing an indane ring, a group NR1 completing a dihydroindole ring, or a group N completing a dihydroindole ring linked via the 1-position;
- W is a bond, and n+m is 1, 2, 3, 4, 5, or 6;
- W is CO, SO, or SO2, n is 2, 3, 4, or 5 and m is 0, 1, 2, or 3, provided that n+m is not more than 6;
- or
- W is O, S, n is 2, 3, 4, or 5, and m is 0, 1, 2, or 3, provided that n+m is not more than 6, and provided that if Y is N completing a dihydroindole ring attached via the 1-position then m is 2, or 3;
- and if Y is NR1 completing a dihydroindole ring linked via the 2-position then m is 1, 2, or 3;
- R1 is
- hydrogen, C1-6-alk(en/yn)yl, C3-8-cycloalk(en)yl, C3-8-cycloalk(en)yl-C1-6-alk(en/yn)yl, aryl, heteroaryl, aryl-C1-6-alkyl, heteroaryl-C1-6alkyl, acyl, thioacyl, C1-6alkylsulfonyl, trifluoromethylsulfonyl, arylsulfonyl, or heteroarylsulfonyl;
- R15VCO— wherein V is O or S and R15 is C1-6-alk(en/yn)yl, C3-8cycloalk(en)yl, C3-8-cycloalk(en)yl-C1-6-alk(en/yn)yl, aryl, or heteroaryl;
- or
- a group R16R17NCO— or R16R17NCS— wherein R16 and R17 are independently hydrogen, C1-6alk(en)/yn)yl, C3-8-cycloalk(en)yl, C3-8-cycloalk(en)yl-C1-6-alk(en/yn)yl, heteroaryl, or aryl, or R16 and R17 together with the N-atom to which they are linked, form a pyrrolidinyl, piperidinyl or perhydroazepin group;
- and
- R2-R5 are independently selected from hydrogen, halogen, cyano, nitro, C1-6-alk(en/yn)yl, C1-6 alkoxy, C1-6-alkylthio, hydroxy, C3-8-cycloalk(en)yl, C3-8-cycloalk(en)yl-C1-6-alk(en/yn)yl, C1-6-alkylcarbonyl, phenylcarbonyl, halogen substituted phenylcarbonyl, trifluoromethyl, trifluoromethylsulfonyloxy and C1-6alkylsulfonyl, one of R2-R5 alternatively being a group —NR13R 14 wherein R13 is as defined for R1 and R14 is hydrogen, C1-6-alk(en/yn)yl, C3-8-cycloalk(en)yl, C3-8-cycloalk(en)yl-C1-6alk(en/yn)yl, aryl, heteroaryl, aryl-C1-6 alkyl, or heteroaryl-C1-6-alkyl, or
- R13 and R14 together with the N-atom to which they are linked form a group 16
- wherein Q is C═O, C═S or CH2;
- T is NH, N-alkyl, S, O or CH2;
- and p is 1-4, inclusive;
- or two adjacent groups taken from R2-R5 may be joined and designate a —(CH2)3—, or —CH═CH—NH—, thereby forming a fused 5 membered ring;
- R6-R9 and R111-R12 are independently hydrogen, halogen, cyano, nitro, C1-6-alk(en/yn)yl, C 1-6-alkoxy, C1-6-alkylthio, hydroxy, C3-8-cycloalk(en)yl, C3-8-cycloalk(en)yl-C1-6alk(en/yn)yl, aryl, heteroaryl, phenylcarbonyl, halogen substituted phenylcarbonyl, trifluoromethyl,
- or
- C1-6 alkylsulfonyl, or two adjacent groups taken from R6-R9 may together form a methylenedioxy group;
- R10 is as defined for R1 above,
- with the proviso that the substituent R3 or R4 in position 6 may not be —NR13R14 when Y is CH2,
- W is a bond, n+m is 1 and the ring is linked via the 1-position;
- or a pharmaceutically acceptable acid addition salt thereof.
23 more elements
A compound of claim, 2, wherein A is a group c) linked to X via the 4, 5, 6, or 7 position.
Dependencies are inferred from the claim text.