IP Library Granted Patent US 7,691,869
Granted Patent B2
US 7,691,869 · App. 12/056,403 · Granted Apr 6, 2010

Pyrrolotriazolopyrimidine derivatives, pharmaceutical compositions containing them and methods of treating conditions and diseases mediated by the adenosine A

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Quick Facts
Patent No.
US 7,691,869
App. No.
12/056,403
Granted
Apr 6, 2010
Kind
B2
Abstract

The present invention provides compounds of the formula wherein R 1 and R 2 have meaning as defined herein in the specification. The compounds of formula (I) are adenosine A 2A receptor antagonists and, thus, may be employed for the treatment of conditions and diseases mediated by the adenosine A 2A receptor activity. Such conditions include, but are not limited to, diseases of the central nervous system such as depression, cognitive function diseases and neurodegenerative diseases such as Parkinson's disease, senile dementia as in Alzheimer's disease or psychoses and stroke. The compounds of the present invention may also be employed for the treatment of attention related disorders such as attention deficit disorder (ADD) and attention deficit hyperactivity disorder (ADHD), extra pyramidal syndrome, e.g., dystonia, akathisia, pseudoparkinsonism and tardive dyskinesia, and disorders of abnormal movement such as restless leg syndrome (RLS) and periodic limb movement in sleep (PLMS); cirrhosis, and fibrosis and fatty liver; dermal fibrosis in diseases such as scleroderma; and the mitigation of addictive behavior. In particular, the compounds of the present invention may be employed to improve motor-impairment due to neurodegenerative diseases such as Parkinson's disease.

Claims (150)

1. A compound of the formula

wherein

R 1 is optionally substituted C 3 -C 7 cycloalkyl, optionally substituted C 6 -C 10 aryl, optionally substituted heteroaryl or optionally substituted heterocyclyl;

R 2 is —(CR 3 -R 4 ) m —Y—(CR 5 —R 6 ) n —Z-Q in which

R 3 , R 4 , R 5 and R 6 are, independently from each other, hydrogen, C 1 -C 6 alkyl or C 3 -C 12 cycloalkyl;

m and n are, independently from each other, an integer from 1 to 6;

Y is absent, CH═CH, C≡C, O, S or NR 7 in which R 7 is hydrogen or C 1 -C 4 alkyl;

Z is absent;

Q is a monovalent radical selected from the group consisting of

R 9 is optionally substituted C 1 -C 6 alkyl, optionally substituted C 3 -C 12 cycloalkyl, optionally substituted C 6 -C 10 aryl, optionally substituted heteroaryl, optionally substituted aralkyl, optionally substituted heteroaralkyl, heterocyclyl or acyl;

R 10 and R 11 are, independently from each other, hydrogen, optionally substituted C 1 -C 3 alkyl; or

R 10 and R 11 , provided they are attached to the same carbon atom, combined are alkylene which together with the carbon atom to which they are attached form a 3- to 7-membered spirocyclic ring;

R 12 , R 13 , R 14 , R 15 , R 16 and R 17 are, independently from each other, hydrogen or optionally substituted C 1 -C 3 alkyl;

X is N or CH;

or a pharmaceutically acceptable salt thereof.

2. A compound according to claim 1 , wherein

R 1 is 5- or 6-membered heteroaryl;

or a pharmaceutically acceptable salt thereof.

3. A compound according to claim 2 , wherein

R 1 is 2-furyl;

or a pharmaceutically acceptable salt thereof.

4. A compound according to claim 3 of the formula

wherein

R 2 is —(CR 3 R 4 ) m —Y—(CR 5 R 6 ) n -Q in which

R 3 , R 4 , R 5 and R 6 are, independently from each other, hydrogen or C 1 -C 6 alkyl;

m is an integer of 1 or 2;

n is an integer from 1 to 4

Y is absent, CH═CH, C≡C or O;

Q is a monovalent radical selected from the group consisting of

R 9 is optionally substituted 01-06 alkyl, optionally substituted monocyclic aryl, optionally substituted heteroaryl, optionally substituted aralkyl, optionally substituted heteroaralkyl or acyl;

R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 are, independently from each other, hydrogen or optionally substituted C 1 -C 3 alkyl;

X is N or OH

or a pharmaceutically acceptable salt thereof.

5. A compound according to claim 4 , wherein

R 2 is —(CR 3 R 4 ) m —Y—(CR 5 R 6 ) n Q in which

R 3 , R 4 , R 5 and R 6 are, independently from each other, hydrogen or C 1 -C 3 alkyl;

m is an integer of 1 or 2

n is an integer from 1 to 4

Y is absent;

Q is a monovalent radical of the formula

R 9 is optionally substituted C 1 -C 6 alkyl, optionally substituted monocyclic aryl, optionally substituted heteroaryl or acyl;

R 10 , R 11 , R 12 and R 13 are hydrogen;

X is N;

or a pharmaceutically acceptable salt thereof.

6. A compound according to claim 5 of the formula

wherein

R 3 , R 4 , R 5 and R 6 are hydrogen;

m and n are 1;

R 9 is optionally substituted C 1 -C 6 alkyl, optionally substituted monocyclic aryl, optionally substituted heteroaryl or acyl;

or a pharmaceutically acceptable salt thereof.

7. A compound according to claim 6 , wherein

R 9 is monocyclic aryl optionally substituted by 1 to 3 halogens;

or a pharmaceutically acceptable salt thereof.

8. A compound according to claim 6 , wherein

R 9 is monocyclic aroyl optionally substituted by 1 to 3 halogens;

or a pharmaceutically acceptable salt thereof.

9. A compound according to claim 6 , wherein

R 9 is C 1 -C 6 alkyl substituted with acyl;

or a pharmaceutically acceptable salt thereof.

10. A compound according to claim 9 , wherein

acyl is optionally substituted monocyclic aroyl or optionally substituted monocyclic heteroaroyl;

or a pharmaceutically acceptable salt thereof.

11. A compound according to claim 10 , wherein

acyl is monocyclic aroyl optionally substituted by 1 to 3 halogens;

or a pharmaceutically acceptable salt thereof.

12. A compound according to claim 1 selected from the group consisting of:

7-(2-(4-(2,5-Difluorophenyl)piperazin-1-yl)ethyl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

7-(2-(4-(2,4-Difluorobenzyl)piperazin-1-yl)ethyl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

2-(Furan-2-yl)-7-(2-(4-((3-methylbenzo[b]thiophen-2-yl)methyl)piperazin-1-yl)ethyl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

7-(2-(4-(2,4-Difluorophenethyl)piperazin-1-yl)ethyl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

7-(2-(4-(3-(2,4-Difluorophenyl)propyl)piperazin-1-yl)ethyl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

(4-(2-(5-Amino-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-7-yl)ethyl)piperazin-1-yl)(2,4-difluorophenyl)methanone;

1-(4-(2-(5-Amino-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-7-yl)ethyl)piperazin-1-yl)-2-(2,4-difluorophenyl)ethanone;

1-(4-(2-(5-Amino-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-7-yl)ethyl)piperazin-1-yl)-3-(2,4-difluorophenyl)propan-1-one;

7-(2-(4-(2,4-Difluorophenyl)-1,4-diazepan-1-yl)ethyl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

7-(2-(4-(2,4-Difluorophenyl)piperidin-1-yl)ethyl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

7-(2-(4-(2,4-Difluorophenyl)piperazin-1-yl)propyl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

7-(3-(4-(2,4-Difluorophenyl)piperazin-1-yl)butyl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

2-(Furan-2-yl)-7-(2-(4-methylpiperazin-1-yl)ethyl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

2-(Furan-2-yl)-7-(2-(4-isopropylpiperazin-1-yl)ethyl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

7-(2-(4-Cyclopentylpiperazin-1-yl)ethyl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

7-(2-(4-Cyclohexylpiperazin-1-yl)ethyl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

7-(2-(4-Cycloheptylpiperazin-1-yl)ethyl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

7-(2-(4-Cyclooctylpiperazin-1-yl)ethyl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

2-(Furan-2-yl)-7-(2-(4-phenylpiperazin-1-yl)ethyl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

7-(2-(4-(2-Fluorophenyl)piperazin-1-yl)ethyl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

7-(2-(4-(3-Fluorophenyl)piperazin-1-yl)ethyl)-2-(furan-2-yl)-7H-pyrrolo[32-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

7-(2-(4-(4-Fluorophenyl)piperazin-1-yl)ethyl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

7-(2-(4-(2,3-Difluorophenyl)piperazin-1-yl)ethyl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

7-(2-(4-(2,6-Difluorophenyl)piperazin-1-yl)ethyl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

2-(Furan-2-yl)-7-(2-(4-(2,4,6-trifluorophenyl)piperazin-1-yl)ethyl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

7-(2-(4-(4-Chlorophenyl)piperazin-1-yl)ethyl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

7-(2-(4-(3,4-Dichlorophenyl)piperazin-1-yl)ethyl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

2-(Furan-2-yl)-7-(2-(4-p-tolylpiperazin-1-yl)ethyl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

2-(Furan-2-yl)-7-(2-(4-(4-methoxyphenyl)piperazin-1-yl)ethyl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

7-(2-(4-(4-Chloro-2-fluorophenyl)piperazin-1-yl)ethyl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

7-(2-(4-(2-Chloro-4-fluorophenyl)piperazin-1-yl)ethyl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

7-(2-(4-(4-Bromo-2-fluorophenyl)piperazin-1-yl)ethyl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

7-(2-(4-(2-Bromo-4-fluorophenyl)piperazin-1-yl)ethyl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

7-(2-(4-(2,4-Dichlorophenyl)piperazin-1-yl)ethyl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

7-(2-(4-(2,4-Dimethylphenyl)piperazin-1-yl)ethyl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

2-(Furan-2-yl)-7-(2-(4-(3-methoxy-5-(trifluoromethyl)phenyl)piperazin-1-yl)ethyl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

7-(2-(4-(3,5-Bis(trifluoromethyl)phenyl)piperazin-1-yl)ethyl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine

2-(Furan-2-yl)-7-(2-(4-(4-nitrophenyl)piperazin-1-yl)ethyl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

2-(Furan-2-yl)-7-(2-(4-(4-(trifluoromethyl)phenyl)piperazin-1-yl)ethyl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

2-(Furan-2-yl)-7-(2-(4-(2-(trifluoromethyl)phenyl)piperazin-1-yl)ethyl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

2-(Furan-2-yl)-7-(2-(4-(4-isopropylphenyl)piperazin-1-yl)ethyl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

7-(2-(4-(4-Butylphenyl)piperazin-1-yl)ethyl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

7-(2-(4-(4-t-Butylphenyl)piperazin-1-yl)ethyl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

7-(2-(4-(3,4-Dimethoxyphenyl)piperazin-1-yl)ethyl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

2-(Furan-2-yl)-7-(2-(4-(2-(methylthio)phenyl)piperazin-1-yl)ethyl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-o]pyrimidin-5-amine;

2-(Furan-2-yl)-7-(2-(4-(3-(methylthio)phenyl)piperazin-1-yl)ethyl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

2-(Furan-2-yl)-7-(2-(4-(4-(trifluoromethoxy)phenyl)piperazin-1-yl)ethyl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine

2-(Furan-2-yl)-7-(2-(4-(pyridin-2-yl)piperazin-1-yl)ethyl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

2-(furan-2-yl)-7-(2-(4-(pyridin-3-yl)piperazin-1-yl)ethyl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

2-(Furan-2-yl)-7-(2-(4-(pyridin-4-yl)piperazin-1-yl)ethyl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

7-(2-(4-(Benzo[d]isothiazol-3-yl)piperazin-1-yl)ethyl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

7-(2-(4-(3-Chloro-5-(trifluoromethyl)pyridin-2-yl)piperazin-1-yl)ethyl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

Methyl 5-(4-(2-(5-amino-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-7-yl)ethyl)piperazin-1-yl)-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxylate;

7-(2-(4-(1H-Indol-4-yl)piperazin-1-yl)ethyl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

5-(4-(2-(5-Amino-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-7-yl)ethyl)piperazin-1-yl)-4-nitrothiophene-2-sulfonamide;

7-(2-(4-(Benzo[d][1,3]dioxol-5-ylmethyl)piperazin-1-yl)ethyl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine

7-(2-(4-((3,5-Dimethyl-1-phenyl-1H-pyrazol-4-yl)methyl)piperazin-1-yl)ethyl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

5-((4-(2-(5-Amino-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-7-yl)ethyl)piperazin-1-yl)methyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione;

2-(Furan-2-yl)-7-(2-(4-(2-methoxyphenyl)piperazin-1-yl)ethyl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

7-(3-(4-(2,4-Difluorophenyl)piperazin-1-yl)propyl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

7-(1-(4-(2,4-Difluorophenyl)piperazin-1-yl)propan-2-yl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine

7-(4-(4-(2,4-Difluorophenyl)piperazin-1-yl)but-2-ynyl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

7-(4-(4-(2,4-Difluorophenyl)piperazin-1-yl)butan-2-yl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

7-(3-(4-(2,4-Difluorophenyl)piperazin-1-yl)-2-methylpropyl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine

7-(2-(4-(2,4-Difluorophenyl)piperazin-1-yl)ethyl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

7-(2-(4-(2,4-Difluorophenyl)piperazin-1-yl)ethyl)-2-phenyl-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

7-(4-(4-(2,4-Difluorophenyl)piperazin-1-yl)butyl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

7-(5-(4-(2,4-Difluorophenyl)piperazin-1-yl)pentyl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

7-(2-(2-(4-(2,4-Difluorophenyl)piperazin-1-yl)ethoxy)ethyl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine

(E)-7-(4-(4-(2,4-Difluorophenyl)piperazin-1-yl)but-2-enyl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine

(Z)-7-(4-(4-(2,4-Difluorophenyl)piperazin-1-yl)but-2-enyl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

7-(2-(4-(2,4-Difluorophenyl)piperazin-1-yl)ethyl)-2-(thiophen-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

7-(2-(4-(2,4-Difluorophenyl)piperazin-1-yl)ethyl)-2-(tetrahydrofuran-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine

2-(Benzofuran-2-yl)-7-(2-(4-(2,4-difluorophenyl)piperazin-1-yl)ethyl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

7-(2-(4-(2,4-Difluorophenyl)piperazin-1-yl)ethyl)-2-(pyridin-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

7-(2-(4-(2,4-Difluorophenyl)piperazin-1-yl)ethyl)-2-(pyridin-3-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

2-(5-Amino-7-(2-(4-(2,4-difluorophenyl)piperazin-1-yl)ethyl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-2-yl)phenol; and

7-(2-(4-(2,4-Difluorophenyl)piperazin-1-yl)ethyl)-2-(furan-3-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine;

or a pharmaceutically acceptable salt thereof.

13. A method of treating Parkinson's disease comprising administering to a mammal, in need thereof, a therapeutically effective amount of a compound according to claim 1 , or a pharmaceutically acceptable salt thereof.

14. A method of treating cirrhosis comprising administering to a mammal, in need thereof, a therapeutically effective amount of a compound according to claim 1 , or a pharmaceutically acceptable salt thereof.

15. A pharmaceutical composition comprising a therapeutically effective amount of at least one compound of claim 1 in combination with one or more pharmaceutically acceptable carriers.

16. The pharmaceutical composition according to claim 15 , for the treatment of Parkinson's disease.

17. The pharmaceutical composition according to claim 15 , wherein the medical condition is for the treatment of cirrhosis.

Assignments (5)
RELEASE OF SECURITY INTEREST Recorded Feb 3, 2011
From: CREDIT SUISSE AG
To: KING PHARMACEUTICALS RESEARCH AND DEVELOPMENT, INC.
Reel/Frame 025738/0132 →
SECURITY AGREEMENT Recorded May 13, 2010
From: KING PHARMACEUTICALS RESEARCH AND DEVELOPMENT, INC.
To: CREDIT SUISSE AG
Reel/Frame 025703/0628 →
RELEASE OF SECURITY INTEREST Recorded May 11, 2010
From: KING PHARMACEUTICALS RESEARCH AND DEVELOPMENT, INC.
To: CREDIT SUISSE AG
Reel/Frame 024369/0022 →
SECURITY AGREEMENT Recorded Dec 30, 2008
From: KING PHARMACEUTICALS RESEARCH & DEVELOPMENT, INC.
To: CREDIT SUISSE, AS AGENT
Reel/Frame 022034/0870 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 5, 2008
From: MOORMAN, ALLAN R.
To: KING PHARMACEUTICALS RESEARCH AND DEVELOPMENT, INC.
Reel/Frame 020903/0676 →