US 6,982,332 B2 | ||
Hybrid 2-aminotetralin and aryl-substituted piperazine compounds and their use in altering CNS activity | ||
Aloke K. Dutta, Novi, Mich. (US) | ||
Assigned to Wayne State University, Detroit, Mich. (US) | ||
Appl. No. 10/344,285 PCT Filed Jun. 07, 2002, PCT No. PCT/US02/18267 § 371(c)(1), (2), (4) Date Feb. 06, 2003, PCT Pub. No. WO02/098367, PCT Pub. Date Dec. 12, 2002. |
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Claims priority of provisional application 60/296622, filed on Jun. 07, 2001. | ||
Prior Publication US 2003/0195219 A1, Oct. 16, 2003 | ||
Int. Cl. C07D 417/12 (2006.01); C07D 403/12 (2006.01); C07D 401/12 (2006.01); C07D 295/13 (2006.01) |
U.S. Cl. 544—253 | 8 Claims |
1. A compound exhibiting CNS activity in mammalian species, having the structure ![]() wherein A is an optionally heterocyclic 5 or 6 membered aromatic ring system; ![]() is an optionally heteroevelic 5 or 6 membered aromatic ring structure wherein X and Y are moieties which complete said 5 or 6 membered aromatic ring system. R2 is selected from the group consisting of C1-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, C4-8 cycloalkyl, C4-8 cycloalkenyl; C6-10 aryl, —NR4q where R4 individually are H, C1-8 alkyl, C2-8 alkenyl, C4-8 cycloalkyl, C4-8 cycloalkenyl, C6-20 aryl and q is 3 or 4, with the proviso that when q is 4, the group bears a positive formal charge; —NR4—C(O)—R4, —NR4—C(O)—NR42 wherein the above hydrocarbon groups may optional be substituted with —CN, C1-4 lower alkyl, —OR4, and halo, or two R2 together may form a fused ring system,
o is an integer from 0 to 4, the upper limit of o bounded by the number of available substitutent sites on said optionally
heterocyclic 5 or 6 membere aromatic ring structure;
n is an integer from 0 to 2;
R1 is selected from the group consisting of C18 alkyl, C2-8 alkenyl, C2-8 alkynyl, C4-8 cycloalkyl, C4-8 cycloalkenyl, C6-10 aryl, each of the foregoing alkyl, a kenyl, alkynyl, cycloalkyl, cycloalkenyl, and aryl groups optionally halo substituted
and/or substituted by —CN, C1-4 lower alkoxy, C1-4 acyloxy, C1-4 acyl, or —C(O)—R4;— —NH—SO2—NR4 where R5 is C1-8 alkylene and r is 2 or 3, with the proviso that when r is 3, the nitrogen of the NR4r group will bear a positive formal charge; —R5—NH—C(O)—R4; —R5—NR4r, —R5—Ar where Ar is an aryl ring system, optionally including one or more heteroatoms; and
p is 1 to 4;
wherein one (CH2)n group may be replaced by O or S;
or a pharmaceutically acceptable salt thereof.
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