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US 7,067,501 B2Granted
Aryloxyphenyl and arylsulfanylphenyl derivatives
AssigneeH. Lundbeck A/S
InventorsGarrick P. Smith, Gitte Mikkelsen, Kim Andersen, Daniel Greve, Thomas Ruhland, Stephen P. Wren
Life of this patent
Estimating the term…
Abstract
The invention provides compounds of the formula wherein the substituents are as defined in the application. The compounds are valuable glycine transport inhibitors.
Claims23
A compound represented by the general formula I
- wherein
- Y is N;
- X represent O or S;
- m is 1;
- p is 0, 1, 2, 3 or 4;
- q is 0, 1 or 2;
- s is 0, 1, 2 or 3;
- r is 0, 1 or 2;
- Q represents C, P—OR5, or S═O, wherein R5 hydrogen or C1-6-alkyl;
- A is OR6, wherein R6 represent hydrogen, C1-6-alkyl, aryl or aryl-C1-6-alkyl, wherein aryl may be substituted with halogen, CF3, OCF3, CN, NO2 or C1-6 alkyl;
- AR represents phenyl;
- each R4 individually represents C1-6-alkyl, C3-8-cycloalkyl or C3-8-cycloalkyl-C1-6-alkyl;
- each R1 is independently selected from the group consisting of C1-6-alkyl, or two R1 attached to the same carbon atom may form a 3–6-membered spiro-attached cycloalkyl;
- each R2 is independently selected from the groups consisting of halogen, cyano, nitro, C1-6-alk(en/yn)yl, C1-6-alk(en/yn)yloxy, C1-6-alk(en/yn)ylsulfanyl, hydroxy, hydroxy-C1-6-alk(en/yn)yl, halo-C1-6-alk(en/yn)yl, halo-C1-6-alk(en/yn)yloxy, C3-8-cycloalk(en)yl, C3-8-cycloalk(en)yl-C1-6-alk(en/yn)yl, acyl, C1-6-alk(en/yn)yloxycarbonyl, C1-6-alk(en/yn)ylsulfonyl or —NR9R10 wherein R9 and R10 independently represent hydrogen, C1-6-alk(en/yn)yl, C3-8-cycloalk(en)yl, C3-8-cycloalk(en)yl-C1-6 alk(en/yn)yl or aryl, or R9 and R10 together with the nitrogen atom to which they are attached form a 3–7-membered ring which optionally contains one further heteroatom selected from the group consisting of nitrogen and oxygen;
- each R3 which is substituted on AR, is independently selected from the group consisting of halogen, cyano, nitro, C1-6-alk(en/yn)yl, C1-6-alk(en/yn)yloxy, C1-6-alk(en/yn)ylsulfanyl, hydroxy, hydroxy-C1-6-alk(en/yn)yl, halo-C1-6-alk(en/yn)yl, halo-C1-6-alk(en/yn)yloxy, C3-8-cycloalk(en)yl, C3-8-cycloalk(en)yl-C1-6-alk(en/yn)yl, C1-6-alk(en/yn)ylsulfonyl, aryl, aryl-C1-6-alk(en/yn)yloxy, aryl-C1-6-alk(en/yn)yl, C1-6-alk(en/yn)yloxycarbonyl, acyl, —NHCO—C1-6-alk(en/yn)yl, —CONR11R12 wherein R11 and R12 independently represent hydrogen, C1-6-alk(en/yn)yl, C3-8-cycloalk(en)yl, C3-8-cycloalk(en)yl-C1-6-alk(en/yn)yl or aryl, or R11 and R12 together with the nitrogen to which they are attached form a 3–7-membered ring which optionally contains one further heteroatom selected from the group consisting of nitrogen and oxygen;
- or NR13R14 wherein R13 and R14 independently represent hydrogen, C1-6-alk(en/yn)yl, C3-8-cycloalk(en)yl, C3-8-cycloalk(en)yl-C1-6-alk(en/yn)yl or aryl;
- or R13 and R14 together with the nitrogen to which they are attached form a 3–7-membered ring which optionally contains one further heteroatom selected from the group consisting of nitrogen and oxygen;
- or an acid addition salt thereof.
15 more elements
Dependencies are inferred from the claim text.