IP Library Granted Patent US 8,598,180
Granted Patent B2
US 8,598,180 · App. 12/852,251 · Granted Dec 3, 2013

Tetrahydroindolone derivatives for treatment of neurological conditions

Inventors: David Reed Helton (Newport Beach, CA); David Brian Fick (Newport Beach, CA); Jason Paul Sharp (San Clemente, CA); Ernest H. Pfadenhauer (Costa Mesa, CA)
Assignee: Abraxis Bioscience, Inc.
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Quick Facts
Patent No.
US 8,598,180
App. No.
12/852,251
Granted
Dec 3, 2013
Kind
B2
Abstract

Compositions comprising tetrahydroindolone derivatives in which the tetrahydroindolone moiety is covalently linked to a substituted arylpiperazine moiety and methods for treating neurological and psychiatric conditions using such compositions are disclosed.

Claims (28)

1. A pharmaceutical composition comprising a compound having the following formula (I):

wherein:

(a) X is CH or N;

(b) R 1 is hydrogen, alkyl, aralkyl, heteroaralkyl, alkenyl, aralkenyl, heteroaralkenyl, aryl, or heteroaryl;

(c) R 2 is hydrogen, alkyl, aralkyl, aryl, or heteroaryl;

(d) R 2 , is hydrogen unless R 2 is methyl, in which case R 2 , is also methyl;

(e) R 3 has the following formula (III):

wherein:

(i) R 4 is hydrogen, alkyl, halo, hydroxy, alkoxy, cyano, nitro, perfluoroalkyl, perfluoroalkoxy, or hydroxymethyl;

(ii) R 5 is hydrogen, alkyl, halo, alkoxy, cyano, nitro, perfluoroalkyl, perfluoroalkoxy, amino, aminocarbonyl, aminosulfonyl, or hydroxymethyl;

(iii) R 6 is alkyl, halo, alkoxy, perfluoroalkyl, perfluoroalkoxy, or nitro;

(iv) R 4 and R 5 when taken together can form a 5 or 6 membered ring and can contain one or more heteroatoms;

(v) R 5 and R 6 when taken together can form a 5 or 6 membered ring and can contain one or more heteroatoms;

(f) L is selected from the group consisting of —(CH 2 ) m —, where m is an integer from 1 to 6, and an alkyl substituted hydrocarbyl moiety of the formula (IV):

wherein:

(i) n is 0, 1 or 2;

(ii) R7 and R8 are hydrogen, methyl or ethyl;

(iii) R9 and R9′ are hydrogen, methyl or ethyl;

(iv) if n is 1 and R7 or R8 is methyl or ethyl, then R9 and R9′ are hydrogen;

(v) if n is 1 and R7 and R8 are hydrogen, then R9 and R9′ are methyl or ethyl; and

(vi) if n is 2, then R9 and R9′ are hydrogen and one or both of R7 and R8 are methyl or ethyl;

and pharmaceutically acceptable salts and esters thereof.

2. The pharmaceutical composition of claim 1 , wherein R 2 and R 2 , are both hydrogen.

3. The pharmaceutical composition of claim 1 , wherein R 4 is selected from the group consisting of hydrogen, halo, and alkoxy.

4. The pharmaceutical composition of claim 1 , wherein R 5 is selected from the group consisting of hydrogen, alkyl, halo, alkoxy, and perfluoroalkyl.

5. The pharmaceutical composition of claim 1 , wherein R 6 is selected from the group consisting of alkyl, halo, alkoxy, and perfluoroalkyl.

6. The pharmaceutical composition of claim 1 , wherein R 4 and R 5 when taken together form a naphthalene ring.

7. The pharmaceutical composition of claim 1 , comprising a pharmaceutically acceptable excipient.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 15, 2011
From: CENOMED BIOSCIENCES, LLC
To: ABRAXIS BIOSCIENCE, INC.
Reel/Frame 026459/0773 →
Continuity (3)
Continuation 10595219
Provisional Application 60505692 · Sep 25, 2003
Related Publication 20100305141A1 · Dec 2, 2010