IP Library Granted Patent US 8,846,661
Granted Patent B2
US 8,846,661 · App. 12/818,764 · Granted Sep 30, 2014

Diazahomoadamantane derivatives and methods of use thereof

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Quick Facts
Patent No.
US 8,846,661
App. No.
12/818,764
Granted
Sep 30, 2014
Kind
B2
Abstract

The invention relates to compounds that are diazahomoadamantane derivatives, compositions comprising such compounds, and methods of using such compounds and compositions.

Claims (177)

1. A compound of formula (I)

wherein

X is CH 2 or C═O;

R is hydrogen, Ar 1 , Ar 2 —Ar 3 , —(CH 2 ) q Ar 3 , —C(O)Ar 3 , —C(O)OAr 3 , —C(O)NR 1 R 2 , —C(O)—(CR x R y ) q —Ar 3 , —C(O)—(CR x R y ) q —O—Ar 3 , —C(O)—Ar 2 —Ar 3 , or (i);

Ar 1 , Ar 2 , and Ar 3 are each independently aryl or heteroaryl;

A is aryl or heteroaryl;

q is 1, 2, 3, 4, or 5;

r and s are independently 0, 1, 2, or 3, wherein the total of r and s is 2, 3 or 4;

R 1 is hydrogen or alkyl;

R 2 is aryl, arylalkyl, heteroaryl, or heteroarylalkyl;

R x and R y , at each occurrence, are each independently hydrogen, alkyl, fluorine, or haloalkyl;

wherein each aryl or heteroaryl or the aryl and heteroaryl moieties on arylalkyl and heteroarylalkyl groups are independently unsubstituted or substituted with 1, 2, 3, 4, or 5 substituents selected from the group consisting of alkyl, alkenyl, alkynyl, halogen, cyano, -G 1 , —NO 2 , —OR 1a , —O—(CR 4a R 5a ) p —O—, —OC(O)R 1a , —OC(O)N(R b )(R 3a ), —SR 1a , —S(O) 2 R 2a , —S(O) 2 N(R b )(R 3a ), —C(O)R 1a , —C(O)OR 1a , —C(O)N(R b )(R 3a ), —N(R b )(R 3a ), —N(R a )C(O)R 1a , —N(R a )C(O)O(R 1a ), —N(R a )C(O)N(R b )(R 3a ), —(CR 4a R 5a ) m —NO 2 , —(CR 4a R 5a ) m —OR 1a , —(CR 4a R 5a ) m —OC(O)R 1a , —(CR 4a R 5a ) m —OC(O)N(R b )(R 3a ), —(CR 4a R 5a ) m —SR 1a , —(CR 4a R 5a ) m —S(O) 2 R 2a , —(CR 4a R 5a )S(O) 2 N(R b )(R 3a ), —(CR 4a R 5a ) m —C(O)R 1a , —(CR 4a R 5a ) m —C(O)OR 1a , —(CR 4a R 5a ) m —C(O)N(R b )(R 3a ), —(CR 4a R 5a ) m —N(R b )(R 3a ), —(CR 4a R 5a ) m —N(R a )C(O)R 1a , —(CR 4a R 5a ) m —N(R a )C(O)O(R 1a ), —(CR 4a R 5a ) m —N(R a )C(O)N(R b )(R 3a ),—(CR 4a R 5a ) m -G 2 , cyanoalkyl, and haloalkyl; wherein

R 1a and R 3a , at each occurrence, are each independently hydrogen, alkyl, haloalkyl, G 2 , or —(CR 6a R 7a ) n -G 2 ;

R 2a , at each occurrence, is independently alkyl, haloalkyl, G 2 , or —(CR 6a R 7a ) n -G 2 ;

R 4a ,R 5a , R 6a , and R 7a , at each occurrence, are each independently hydrogen, halogen, alkyl, or haloalkyl;

R a and R b , at each occurrence, are each independently hydrogen, alkyl, or haloalkyl;

m and n, at each occurrence, are each independently 1, 2, 3, 4, or 5;

p, at each occurrence, is 1 or 2;

—O—(CR 4a R 5a ) p —O— is a divalent substituent attached to two adjacent carbon atoms of the aryl or heteroaryl;

G 1 , at each occurrence, is heterocycle or cycloalkyl, wherein each G 1 is independently unsubstituted or substituted with 1, 2, 3, 4, or 5 substituents selected from the group consisting of alkyl, alkenyl, alkynyl, halogen, cyano, oxo, —NO 2 , —OR 1b , —OC(O)R 1b , —OC(O)N(R b )(R 3b ), —SR 1b , —S(O) 2 R 2b , S(O) 2 N(R b )(R 3b ), —C(O)R 1b , —C(O)OR 1b , —C(O)N (R b )(R 3b ), —N(R b )(R 3b ), —N(R a )C(O)R 1b , —N(R a )C(O)O(R 1b ), —N(R a )C(O)N(R b )(R 3b ), —(CR 4b R 5b ) m —NO 2 , —(CR 4b R 5b ) m , —OR 1b , —(CR 4b R 5b ) m —OC(O)R 1b , —(CR 4b R 5b ) m —OC(O)N(R b )(R 3b ), —(CR 4b R 5b ) m —SR 1b , —(CR 4b R 5b ) m —S(O) 2 R 2b , —(CR 4b R 5b ) m —S(O) 2 N(R b )(R 3b ), —(CR 4b R 5b ) m —C(O)R 1b , —(CR 4b R 5b ) m —C(O)OR 1b , —(CR 4b R 5b ) m —C(O)N(R b )(R 3b ), —(CR 4b R 5b ) m —N(R b )(R 3b ), —(CR 4b R 5b ) m —N(R a )C(O)R 1b , —(CR 4b R 5b ) m —N(R a )C(O)O(R 1b ), —(CR 4b R 5b ) m —N(R a )C(O)N(R b )(R 3b ), cyanoalkyl, and haloalkyl;

R 1b and R 3b , at each occurrence, are each independently hydrogen, alkyl, or haloalkyl;

R 2b , at each occurrence, is independently alkyl or haloalkyl;

R 4b and R 5b , at each occurrence, are each independently hydrogen, halogen, alkyl, or haloalkyl; and

G 2 , at each occurrence, is aryl, heteroaryl, heterocycle, or cycloalkyl, wherein each G 2 is independently unsubstituted or substituted with 1, 2, 3, 4, or 5 substituents selected from the group consisting of alkyl, alkenyl, alkynyl, halogen, cyano, oxo, —NO 2 , —OR 1b , —OC(O)R 1b , —OC(O)N(R b )(R 3b ), —SR 1b , —S(O) 2 R 2b , —S(O) 2 N(R b )(R 3b ), —C(O)R 1b , —C(O)OR 1b , —C(O)N(R b )(R 3b ), —N(R b )(R 3b ), —N(R a )C(O)R 1b , —N(R a )C(O)O(R 1b ), —N(R a )C(O)N(R b )(R 3b ), —(CR 4b R 5b ) m —NO 2 , —(CR 4b R 5b ) m —OR 1b , —(CR 4b R 5b ) m —OC(O)R 1b , —(CR 4b R 5b ) m —OC(O)N(R b )(R 3b ), —(CR 4b R 5b ) m —SR 1b , —(CR 4b R 5b ) m —S(O) 2 R 2b , —(CR 4b R 5b ) m —S(O) 2 N(R b )(R 3b ), —(CR 4b R 5b ) m —C(O)R 1b , —(CR 4b R 5b ) m —C(O)OR 1b , —(CR 4b R 5b ) m —C(O)N(R b )(R 3b ), —(CR 4b R 5b ) m —N(R b )(R 3b ), —(CR 4b R 5b ) m —N(R a )C(O)R 1b , —(CR 4b R 5b ) m —N(R a )C(O)O(R 1b ), —(CR 4b R 5b ) m —N(R a )C(O)N(R b )(R 3b ), cyanoalkyl, and haloalkyl;

or a pharmaceutically acceptable salt, amide, or ester thereof.

2. The compound of claim 1 , wherein R is Ar 1 .

3. The compound of claim 2 , wherein X is CH 2 , and Ar 1 is a bicyclic or tricyclic heteroaryl optionally oxidized on an oxidizable nitrogen or sulfur and either unsubstituted or substituted with 1, 2, or 3 substituents selected from halogen or alkyl.

4. The compound of claim 1 , wherein R is Ar 2 —Ar 3 or —C(O)—Ar 2 —Ar 3 .

5. The compound of claim 4 , wherein

X is CH 2 ,

Ar 2 is heteroaryl selected from oxadiazolyl, pyridazinyl, pyrazolyl, pyridinyl, thiadiazolyl or 1,3-thiazolyl;

Ar 3 is phenyl or heteroaryl, wherein the phenyl or heteroaryl is unsubstituted or substituted with 1, 2, 3, or 4 substituents selected from alkyl, halogen, cyano, —OR 1a , —O—(CR 4a R 5a ) p —O—, —C(O)R 1a , —N(R b )(R 3a ), —N(R a )C(O)R 1a , or haloalkyl; wherein

R 1a and R 3a , at each occurrence, are each independently alkyl or haloalkyl;

R 4a and R 5a , at each occurrence, are each independently hydrogen or alkyl; and

R b , at each occurrence, are each independently hydrogen, alkyl, or haloalkyl.

6. The compound of claim 1 , wherein R is —C(O)Ar 3 or —C(O)OAr 3 .

7. The compound of claim 6 , wherein

X is CH 2 ;

Ar 3 is phenyl or heteroaryl, wherein heteroaryl is selected from pyridinyl, furanyl, benzofuranyl, indolyl, thienyl, benzothienyl, pyrazinyl, quinolinyl, pyrrolyl, thieno[3,2-b]pyridin-5-yl or indazolyl, and wherein the phenyl or heteroaryl is unsubstituted or substituted with 1, 2, 3, or 4 substituents selected from alkyl, halogen, cyano, —OR 1a , —N(R b )(R 3a ), —N(R a )C(O)R 1a , or haloalkyl; wherein

R 1a and R 3a , at each occurrence, are each independently alkyl or haloalkyl; and

R b is hydrogen, alkyl, or haloalkyl.

8. The compound of claim 1 , wherein R is —(CH 2 ) q Ar 3 .

9. The compound of claim 1 , wherein R is —C(O)NR 1 R 2 .

10. The compound of claim 1 , wherein R is —C(O)—(CR x R y ) q —Ar 3 or —C(O)—(CR x R y ) q —O—Ar 3 .

11. The compound of claim 10 , wherein

X is CH 2 ;

R x and R y , at each occurrence, are each independently hydrogen or alkyl;

q is 1 or 2;

Ar 3 is phenyl, naphthyl or thienyl, wherein the phenyl, naphthyl or thienyl is unsubstituted or substituted with 1, 2, 3, or 4 substituents selected from alkyl, halogen, cyano, —OR 1a , —N(R b )(R 3a ), —N(R a )C(O)R 1a , or haloalkyl; wherein

R 1a and R 3a , at each occurrence, are each independently alkyl or haloalkyl; and

R b is hydrogen, alkyl, or haloalkyl.

12. The compound of claim 1 , wherein R is (i)

13. The compound of claim 12 , wherein

X is CH 2 ;

A is phenyl;

R x and R y , at each occurrence, are each independently hydrogen or alkyl; and

r and s are independently 0, 1, or 2, wherein the total of r and s is 2 or 3.

14. The compounds of claim 1 , wherein R is hydrogen.

15. The compound of claim 14 , that is selected from the group consisting of:

1,4-diazatricyclo[4.3.1.1 3,8 ]undecan-5-one; and

1,4-diazatricyclo[4.3.1.1 3,8 ]undecane.

16. A compound or pharmaceutically salt thereof, or amide thereof, the compound is selected from the group consisting of:

4-(thieno[2,3-c]pyridin-5-ylcarbonyl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-(thieno[3,2-b]pyridin-5-ylcarbonyl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-(5,5-dioxidodibenzo[b,d]thien-3-yl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-(5-phenyl-1,3,4-oxadiazol-2-yl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-(6-phenylpyridazin-3-yl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-[6-(1-benzothien-5-yl)pyridazin-3-yl]-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-(3-methoxybenzoyl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-(1-naphthylacetyl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-(pyridin-2-ylcarbonyl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-(phenoxyacetyl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-(3-chlorobenzoyl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

N-[4-(1,4-diazatricyclo[4.3.1.1 3,8 ]undec-4-ylcarbonyl)phenyl]-N,N-dimethylamine;

4-[(2-methylphenyl)acetyl]-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

3-(1,4-diazatricyclo[4.3.1.1 3,8 ]undec-4-ylcarbonyl)benzonitrile;

4-(2-methylbenzoyl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

N-[4-(1,4-diazatricyclo[4.3.1.1 3,8 ]undec-4-ylcarbonyl)phenyl]acetamide;

4-[(3-methylphenyl)acetyl]-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-(2,5-dimethylbenzoyl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-(3-phenylpropanoyl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

N-[3-(1,4-diazatricyclo[4.3.1.1 3,8 ]undec-4-ylcarbonyl)phenyl]acetamide;

4-(4-ethylbenzoyl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4- {[2-(trifluoromethyl)phenyl]acetyl}-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-(2,4-dimethylbenzoyl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-(3-phenylbutanoyl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-(1,2,3,4-tetrahydronaphthalen-2-ylcarbonyl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-(4-ethoxybenzoyl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

N-{4-[2-(1,4-diazatricyclo[4.3.1.1 3,8 ]undec-4-yl)-2-oxoethyl]phenyl}-N,N-dimethylamine;

4-(2,3-difluorobenzoyl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-(3-methylbenzoyl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-(2,5-dimethyl-3-furoyl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-(pyridin-3-ylcarbonyl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-(5-chloro-2-fluorobenzoyl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-(3-methyl-2-furoyl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4- [(1-phenyl-1H-pyrazol-5-ybcarbonyl]-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-(1H-indol-5-ylcarbonyl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-(3,5-dimethoxybenzoyl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-[(4-methylthien-2-yl)carbonyl]-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-[(2,5-dimethoxyphenyl)acetyl]-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-[(5-methylthien-2-yl)carbonyl]-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-(2-fluorobenzoyl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-[(2-fluorophenyl)acetyl]-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-[4-(trifluoromethyl)benzoyl]-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-(3,4-difluorobenzoyl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-(thien-2-ylcarbonyl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-[(5-methylpyrazin-2-yl)carbonyl]-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-(2,3-dimethylbenzoyl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-(quinolin-2-ylcarbonyl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-(thien-2-ylacetyl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-[(3-methoxyphenyl)acetyl]-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-[(1-methyl-1H-pyrrol-2-yl) carbonyl]-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

2-(1,4-diazatricyclo[4.3.1.1 3,8 ]undec-4-ylcarbonyl)phenol;

4-[(2-methoxypyridin-3-yl) carbonyl]-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-(1H-pyrrol-2-ylcarbonyl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-(3-chloro-4-fluorobenzoyl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-(1H-indazol-3-ylcarbonyl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-(5-chloro-2-methoxybenzoyl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-(2,4-difluorobenzoyl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-(thien-3-ylacetyl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-(4-fluoro-3-methylbenzoyl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-(2-furoyl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-benzoyl-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-(2-methoxybenzoyl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-[5-(3-fluoro-4-methoxyphenyl)pyridin-3-yl]-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-[5-(2,3-dihydro-1,4-benzodioxin-6-yl)pyridin-3-yl]-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

N-{4-[5-(1,4-diazatricyclo[4.3.1.1 3,8 ]undec-4-yl)pyridin-3-yl]phenyl}-N,N-dimethylamine;

4-[5-(3,4,5-trimethoxyphenyl)pyridin-3-yl]-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-[5-(3,5-dimethylisoxazol-4-yl)pyridin-3-yl]-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-[5-(2,6-dimethoxyphenyl)pyridin-3-yl]-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-(5-phenylpyridin-3-yl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-[5-(4-methylphenyl)pyridin-3-yl]-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-[5-(4-fluorophenyl)pyridin-3-yl]-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-[5-(4-methoxyphenyl)pyridin-3-yl]-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-{5-[4-(trifluoromethyl)phenyl]pyridin-3-yl}-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-[5-(3-methylphenyl)pyridin-3-yl]-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-[5-(3-fluorophenyl)pyridin-3-yl]-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-[5-(3-methoxyphenyl)pyridin-3-yl]-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-[5-(2-furyl)pyridin-3-yl]-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-(5-thien-3-ylpyridin-3-yl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-[5-(3,4-dimethoxyphenyl)pyridin-3-yl]-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-(3,3′-bipyridin-5-yl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-(3,4′-bipyridin-5-yl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-[5-(2-methoxyphenyl)pyridin-3-yl]-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-[5-(2,5-dimethoxyphenyl)pyridin-3-yl]-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-[5-(2,4-dimethoxyphenyl)pyridin-3-yl]-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-[5-(2-fluorophenyl)pyridin-3-yl]-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-[5-(2-ethoxyphenyl)pyridin-3-yl]-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-[5-(1,4-diazatricyclo[4.3.1.1 3,8 ]undec-4-yl)pyridin-3-yl]benzonitrile;

3-[5-(1,4-diazatricyclo[4.3.1.1 3,8 ]undec-4-yl)pyridin-3-yl]benzonitrile;

4-{5-[3-(trifluoromethyl)phenyl]pyridin-3-yl}-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-[5-(1,3-benzodioxol-5-yl)pyridin-3-yl]-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-(2′-methoxy-3,3′-bipyridin-5-yl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

N-{3-[5-(1,4-diazatricyclo[4.3.1.1 3,8 ]undec-4-yl)pyridin-3-yl]phenyl}acetamide;

4-[5-(3,5-difluorophenyl)pyridin-3-yl]-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-(6′-methoxy-3,3′-bipyridin-5-yl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-[5-(2-methoxy-5-methylphenyl)pyridin-3-yl]-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-[5-(4-methoxy-3-methylphenyl)pyridin-3-yl]-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-[5-(3,4-difluorophenyl)pyridin-3-yl]-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

1-{5-[5-(1,4-diazatricyclo[4.3.1.1 3,8 ]undec-4-yl)pyridin-3-yl]thien-2-yl}ethanone;

4-(5-pyrimidin-5-ylpyridin-3-yl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

1-{2-[5-(1,4-diazatricyclo[4.3.1.1 3,8 ]undec-4-yl)pyridin-3-yl]phenyl}ethanone;

4-[5-(1H-indol-5-yl)pyridin-3-yl]-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-[5-(1H-indol-4-yl)pyridin-3-yl]-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-[5-(4-methoxyphenyl)-1,3-thiazol-2-yl]-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-[5-(4-methylphenyl)-1,3-thiazol-2-yl]-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-[5-(3-methylphenyl)-1,3-thiazol-2-yl]-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-[5-(3-fluorophenyl)-1,3-thiazol-2-yl]-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-[5-(2,5-dimethoxyphenyl)-1,3-thiazol-2-yl]-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-[5-(4-fluorophenyl)-1,3-thiazol-2-yl]-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-(6-chloro-1,3-benzothiazol-2-yl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane;

4-(6-chloro-1,3-benzoxazol-2-yl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane; and

4-(1,3-benzothiazol-2-yl)-1,4-diazatricyclo[4.3.1.1 3,8 ]undecane.

17. A method for treating a disorder selected from the group consisting of acute pain, chronic pain, neuropathic pain, nociceptive pain, allodynia, inflammatory pain, neuralgia, rheumatoid arthritic pain, osteoarthritic pain, back pain, eye pain, cancer pain, dental pain, pelvic pain, post operative pain, post stroke pain, and menstrual pain, said method comprising the step of administering to a subject in need thereof the compound of claim 16 , or a pharmaceutically acceptable salt, or amide thereof.

18. A method for treating a disorder selected from the group consisting of schizophrenia and Alzheimer's disease, comprising the step of administering to a subject in need thereof the compound of claim 16 , or a pharmaceutically acceptable salt, or amide thereof and one or more atypical antipsychotics.

19. A pharmaceutical composition comprising a therapeutically effective amount of the compound of claim 16 , or a pharmaceutically acceptable salt, or amide thereof in combination with one or more pharmaceutically acceptable carriers.

20. The pharmaceutical composition of claim 19 further comprising one or more atypical antipsychotics.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 2, 2013
From: ABBOTT LABORATORIES
To: ABBVIE INC.
Reel/Frame 030137/0198 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 18, 2010
From: SCHRIMPF, MICHAEL R.; SIPPY, KEVIN B.
To: ABBOTT LABORATORIES
Reel/Frame 024560/0400 →