Azabicyclic compounds are central nervous system active agents

1. A compound of formula (IV)

wherein

represents a double bond;

Y is a covalent bond;

Z is CH 2 ;

R 1 is hydrogen:

R 2 is hydrogen;

R 3 and R 5 are absent; and

R 4 is heterocycle, wherein the heterocycle is selected from the group consisting of furyl, imidazolyl, isothiazolyl, isoxazolyl, oxadiazolyl, oxazolyl, pyrazinyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrrolyl, tetrazinyl, tetrazolyl, thiadiazolyl, thiazolyl, thienyl, triazinyl, triazolyl, benzimidazolyl, benzothiazolyl, benzothienyl, benzoxazolyl, benzofuranyl, cinnolinyl, furo[2,3-c]pyridine, furo[3,2-c]pyridine, furo[3,2-b]pyridinyl, furo[2,3-b]pyridinyl, imidazo[1,2-a]pyridinyl, indazolyl, indolyl, indolizinyl, naphthyridinyl, isobenzofuranyl, isobenzothienyl, isoindolyl, isoquinolinyl, phthalazinyl, quinolinyl, quinolizinyl, quinoxalinyl, quinazolinyl, thieno[2,3-c]pyridine, thieno[3,2-c]pyridine, thieno[3,2-b]pyridinyl, and thieno[2,3-b]pyridinyl wherein the heterocycle is substituted with 0, 1, 2, or 3 substituents independently selected from the group consisting of alkenyl, alkoxy, alkoxyalkoxy, alkoxyalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkyl, alkylcarbonyl, alkylcarbonyloxy, alkylthio, alkynyl, carboxy, carboxyalkyl, cyano, cyanoalkyl, formyl, formylalkyl, haloalkoxy, haloalkyl, halogen, hydroxy, hydroxyalkyl, mercapto, mercaptoalkyl, nitro, phenyl, triphenylmethyl (trityl), —C(NH)NR 10 R 11 , —NR 10 R 11 , (NR 10 R 11 )alkyl, (NR 10 R 11 )carbonyl, (NR 10 R 11 )carbonylalkyl, (NR 10 R 11 )sulfonyl, —NR 12 S(O) 2 R 13 , —C(NR 12 )NR 13 R 14 , —CH 2 C(NR 12 )NR 13 R 14 , —C(NOR 12 )R 13 , —C(NCN)R 12 , —C(NNR 12 R 13 )R 14 , —S(O) 2 OR 12 , and —S(O) 2 R 12 ,

wherein R 10 and R 11 are independently selected from hydrogen, alkyl or alkylcarbonyl, and R 12 , R 13 , and R 14 are independently selected from hydrogen, alkyl, aryl, or arylalkyl.

2. The compound according to claim 1 wherein the heterocycle is selected from the group consisting of imidazolyl, isoxazolyl, pyridazinyl, tetrazolyl, thiadiazolyl, thiazolyl, thienyl, imidazo[1,2-a]pyridinyl, thieno[3,2-b]pyridinyl, and thieno[2,3-b]pyridinyl wherein the heterocycle is substituted with 0, 1, or 2 substituents independently selected from the group consisting of alkenyl, alkenyloxy, alkoxy, alkyl, alkynyl, cyano, halogen, nitro, phenyl, (NR 10 R 11 )sulfonyl, and —C(NH)NR 10 R 11 .

3. The compound according to claim 2 selected from the group consisting of

(cis)-5-(3-methyl-5-isoxazolyl)-1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrole;

(cis)-2-methyl-5-(3-methyl-5-isoxazolyl)-1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrole;

(cis)-5-(3-bromo-1,2,4-thiadiazol-5-yl)-1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrole;

(cis)-5-(1,3-thiazol-2-yl)-1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrole;

(cis)-5-(3,5-dimethyl-4-isoxazolyl)-1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrole;

(cis)-5-(1H-imidazol-4-yl)-1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrole;

(cis)-5-(1,3-thiazol-5-yl)-1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrole;

(cis)-5-(imidazo[1,2-a]pyridin-3-yl)-1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrole;

(cis)-5-(imidazo[1,2-a]pyridin-6-yl)-1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrole;

(cis)-5-(thieno[3,2-b]pyridin-2-yl)-1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrole;

(cis)-5-(1-trityl-1H-imidazol-4-yl)-1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrole;

(cis)-5-(5-(aminosulfonyl)-2-thienyl)-1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrole;

(cis)-5-(5-(amino(imino)methyl)-2-thienyl)-1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrole;

(cis)-5-(2-methyl-2H-tetrazol-5-yl)-1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrole;

(cis)-5-(thieno[2,3-b]pyridin-5-yl)-1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrole;

(cis)-5-(imidazo[1,2-a]pyridin-7-yl)-1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrole;

(cis)-5-(5-nitro-1,3-thiazol-2-yl)-1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrole;

(cis)-5-(1,3,4-thiadiazol-2-yl)-1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrole;

(cis)-5-(6-phenylpyridazin-3-yl)-1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrole; and

(cis)-2-methyl-5-(6-phenylpyridazin-3-yl)-1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrole.

4. The compound according to claim 1 wherein the heterocycle is pyridinyl substituted with 0, 1, or 2 substituents independently selected from the group consisting of alkenyl, alkenyloxy, alkoxy, alkyl, alkynyl, cyano, halogen, and nitro.

5. The compound according to claim 4 selected from the group consisting of

(cis)-5-(6-chloro-3-pyridinyl)-1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrole;

(cis)-5-(5-methoxy-3-pyridinyl)-1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrole;

(cis)-5-(6-chloro-5-methyl-3-pyridinyl)-1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrole;

(cis)-5-(3-pyridinyl)-1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrole;

(cis)-5-(5,6-dichloro-3-pyridinyl)-1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrole;

(cis)-5-(5-chloro-3-pyridinyl)-1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrole;

(cis)-5-(6-methyl-3-pyridinyl)-1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrole;

(cis)-5-(2-methyl-3-pyridinyl)-1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrole;

(cis)-5-(6-chloro-5-fluoro-3-pyridinyl)-1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrole;

(cis)-5-(6-chloro-3-pyridinyl)-2-cyanomethyl-1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrole;

(cis)-5-(6-fluoro-3-pyridinyl)-1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrole;

(cis)-5-(2-pyridinyl)-1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrole;

(cis)-5-(4-pyridinyl)-1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrole;

(cis)-5-(6-methyl-2-pyridinyl)-1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrole;

(cis)-5-(5-bromo-3-pyridinyl)-1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrole;

(cis)-5-(5-vinyl-3-pyridinyl)-1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrole;

(cis)-5-(1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrol-5-yl)nicotinonitrile;

(3aS,6aR)-5-(6-chloro-3-pyridinyl)-1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrole; and

(3aR,6aS)-5-(6-chloro-3-pyridinyl)-1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrole.