Dihydrobenzofuranyl alkanamine derivatives and methods for using same Number:7,435,837 from the United States Patent and Trademark Office (PTO) owispatent Compounds of Formula 1 or pharmaceutically acceptable salts thereof are provided: ##STR00001## which are agonists or partial agonists of the 2C subtype of brain serotonin receptors. The compounds, and compositions containing the compounds, can be used to treat a variety of central nervous system disorders such as schizophrenia.<H Dihydrobenzofuranyl, derivatives, Dihydrobenzofur, 7435837.html, Patent, pto, 7435837

Title: Dihydrobenzofuranyl alkanamine derivatives and methods for using same

Abstract: Compounds of Formula 1 or pharmaceutically acceptable salts thereof are provided: ##STR00001## which are agonists or partial agonists of the 2C subtype of brain serotonin receptors. The compounds, and compositions containing the compounds, can be used to treat a variety of central nervous system disorders such as schizophrenia.

Patent Number: 7,435,837 Issued on 10/14/2008 to Gross, et al.

Inventors: Gross; Jonathan Laird (Cranbury, NJ), Williams; Marla Jean (Whitehouse Station, NJ), Stack; Gary Paul (Ambler, PA), Gao; Hong (Belle Mead, NJ), Zhou; Dahui (East Brunswick, NJ)
Assignee: Wyeth (Madison, NJ)

Appl. No.: 10/970,714

Filed: October 21, 2004

Related U.S. Patent Documents


Application Number	Filing Date	Patent Number	Issue Date
60514454	Oct., 2003

Current U.S. Class: 549/467

Current International Class: C07D 307/81 (20060101); C07D 307/80 (20060101)

Field of Search: 549/467

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Primary Examiner: Seaman; D. Margaret
Assistant Examiner: Chandrakumar; Nizal S
Attorney, Agent or Firm: Knight; Julie Anne Robidoux; Andrea L. Choate Hall & Stewart LLP

Parent Case Text

CROSS-REFERENCE TO RELATED APPLICATIONS

The present invention claims priority benefit of U.S. Provisional Application Ser. No. 60/514,454, filed Oct. 24, 2003, which is incorporated herein by reference in its entirety for all purposes.

Claims

What is claimed:

1. A compound of Formula 1: ##STR00024## or pharmaceutically acceptable salt thereof; wherein: R and R' are, independently, hydrogen, alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, or alkylcycloalkyl of 4 to 12 carbon atoms having 3 to 6 carbons in the cycloalkyl ring; alternatively R and R' can be taken together with the nitrogen to which they are attached to form a ring containing 2-5 carbon atoms, wherein one of the ring carbon atoms is optionally replaced by nitrogen, sulfur or oxygen; R.sup.1, R.sup.2, R.sup.3a and R.sup.3b are, independently, hydrogen or lower alkyl; R.sup.4, R.sup.5, and R.sup.6 are, independently, hydrogen, halogen, cyano, hydroxyl, carboxyl, alkyl of 1 to 8 carbon atoms, perfluoroalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, perfluoroalkoxy of 1 to 6 carbon atoms, aryl of 6 and 10 carbon atoms, aryloxy of 6 and 10 carbon atoms, 5 to 10 membered heteroaryl having 1 to 3 heteroatoms each independently selected from nitrogen, oxygen or sulfur, alkenyl of 2 to 8 carbon atoms, alkanoyl of 2 to 6 carbon atoms, alkanoyloxy of 2 to 6 carbon atoms, carboalkoxy of 2 to 6 carbon atoms, carboxamido, alkanamido of 2 to 6 carbon atoms, alkanesulfonamido of 1 to 6 carbon atoms, amino, monoalkylamino of 1 to 6 carbon atoms, dialkylamino of 1 to 6 carbon atoms per alkyl moiety, cycloalkyl of 3 to 8 carbon atoms, or 3 to 8 membered heterocycloalkyl having 1 to 3 heteroatoms each independently selected from nitrogen, oxygen or sulfur, wherein the cycloalkyl and heterocycloalkyl groups are saturated or partially saturated; and n is 1 or 2; R.sup.7 is branched alkyl of 3 to 8 carbon atoms, branched alkenyl of 3 to 8 carbon atoms, or --Y--R.sup.8, wherein Y is a direct bond, and R.sup.8 is aryl of 6 and 10 carbon atoms substituted with 1 to 5 groups independently selected from halogen, hydroxyl, cyano, alkyl of 1 to 6 carbon atoms, perfluoroalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, or perfluoroalkoxy of 1 to 6 carbon atoms, 5 to 10 membered heteroaryl, cycloalkyl of 3 to 8 carbon atoms, or 3 to 8 membered heterocycloalkyl, wherein the cycloalkyl and heterocycloalkyl groups are saturated or partially saturated; and wherein, unless otherwise indicated, any aryl, heteroaryl, cycloalkyl or heterocycloalkyl may optionally be substituted with 1 to 5 substituents independently selected from halogen, hydroxyl, cyano, alkyl of 1 to 6 carbon atoms, perfluoroalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, or perfluoroalkoxy of 1 to 6 carbon atoms.

2. The compound of claim 1 wherein: R' is hydrogen; and R is hydrogen, alkyl of 1 to 6 carbon atoms, or perfluoroalkyl of 1 to 6 carbon atoms.

3. The compound of claim 1 wherein R and R' are, independently, hydrogen or alkyl of 1 to 6 carbon atoms.

4. The compound according to claim 1 wherein R.sup.7 is --Y--R.sup.8, wherein Y is a direct bond, and R.sup.8 is aryl of 6 and 10 carbon atoms substituted with 1 to 5 groups independently selected from halogen, hydroxyl, cyano, alkyl of 1 to 6 carbon atoms, perfluoroalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, or perfluoroalkoxy of 1 to 6 carbon atoms, 5 to 10 membered heteroaryl, cycloalkyl of 3 to 8 carbon atoms, or 3 to 8 membered heterocycloalkyl as defined in claim 1, and R.sup.4, R.sup.5, and R.sup.6 are, independently, hydrogen, halogen, alkyl of 1 to 8 carbon atoms, perfluoroalkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, alkenyl of 2 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, 3 to 8 membered heterocycloalkyl, aryl of 6 and 10 carbon atoms, or 5 to 10 membered heteroaryl, and wherein any aryl, heteroaryl, cycloalkyl or heterocycloalkyl may optionally be substituted with 1 to 5 substituents independently selected from halogen, hydroxyl, cyano, alkyl of 1 to 6 carbon atoms, perfluoroalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, or perfluoroalkoxy of 1 to 6 carbon atoms.

5. The compound of claim 1 wherein R.sup.4, R.sup.5, R.sup.6 are, independently, hydrogen, halogen, alkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, perfluoroalkyl of 1 to 3 carbon atoms, or perfluoroalkoxy of 1 to 3 carbon atoms.

6. The compound of claim 1 wherein at least one of R.sup.4 and R.sup.5 is halogen, alkyl of 1 to 6 carbon atoms, perfluoroalkyl of 1 to 3 carbon atoms, or alkoxy of 1 to 6 carbon atoms.

7. The compound of claim 1 wherein R.sup.7 is phenyl, substituted with 1 to 5 substituents independently selected from halogen, hydroxyl, alkyl of 1 to 6 carbon atoms, perfluoroalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, or perfluoroalkoxy of 1 to 6 carbon atoms.

8. The compound of claim 7 wherein R.sup.7 is phenyl, substituted with 1 to 3 substituents independently selected from halogen, alkyl of 1 to 3 carbon atoms, perfluoroalkyl of 1 to 3 carbon atoms, or alkoxy of 1 to 3 carbon atoms.

9. A compound of claim 8 wherein n is 1.

10. The compound of claim 9 wherein R.sup.7 is phenyl, substituted with 1 to 3 substituents selected from fluoro, chloro, methyl, methoxy or trifluoromethyl.

11. The compound of claim 10 wherein R.sup.5 is halo and each of R, R', R.sup.1, and R.sup.2 are hydrogen.

12. The compound of claim 11 wherein R.sup.3a and R.sup.3b are both hydrogen.

13. The compound of claim 1, wherein R.sup.7 is selected from the group consisting of: 4-methoxy-2-methylphenyl, 2-chloro-4-(trifluoromethyl)phenyl, 2-chloro-4-methoxyphenyl, 2-chloro-4-(trifluoromethoxy)phenyl, ({7-[4-methoxy-2-(trifluoromethyl)phenyl, 4-ethoxy-2-methylphenyl, 4-ethoxy-2-(trifluoromethyl)phenylamine, 4-chloro-2-(trifluoromethyl)phenyl, 4-fluoro-2-(trifluoromethyl)phenyl, 2-ethyl-4-methoxyphenyl, 2,4-dichlorophenyl, 2,4-dimethylphenyl, 4-isopropyl-2-methoxyphenyl, 4-isopropoxy-2-(trifluoromethyl)phenyl, 2-chloro-4-isopropoxyphenyl, 4-chloro-2-methylphenyl, 2,6-difluorophenyl, 2-chloro-6-fluorophenyl, 2-fluoro-6-(trifluoromethyl)phenyl, 2,6-bis(trifluoromethyl)phenyl, 2,3-dichlorophenyl, 3-chloro-2-fluorophenyl, 2-chloro-3-methylphenyl, 2,6-dichloro-4-methoxyphenyl, and 5-fluoro-2-methoxyphenyl.

14. The compound of claim 1 wherein R.sup.4 or R.sup.5 is aryl of 6 and 10 carbon atoms, said aryl optionally substituted with 1 to 5 substituents independently selected from halogen, hydroxyl, alkyl of 1 to 6 carbon atoms, perfluoroalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, or perfluoroalkoxy of 1 to 6 carbon atoms.

15. The compound of claim 1 which is: (.+-.)-1-[7-(2,3-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamin- e, (.+-.)-{[7-(2,3-dimethoxyphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}a- mine, (-)-{[(7-(2,3-dimethoxyphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}- amine, (+)-{[(7-(2,3-dimethoxyphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl- }amine, (+)-{[7-(4-chloro-2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]me- thyl}amine, (-)-{[7-(4-chloro-2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}am- ine, (.+-.)-{[7-(2,3-difluorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}- amine, (.+-.)-{[7-(2,5-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methy- l}amine, (.+-.)-{[7-(2,5-dimethoxyphenyl)-2,3-dihydro-1-benzofuran-2-yl]me- thyl}amine, (.+-.)-{[7-(2,5-dichlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}amin- e, (+)-{[7-(2,5-dichlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}amine- , (-)-{[7-(2,5-dichlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}amine, (.+-.)-{[7-(2,4,6-trichlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}a- mine, (.+-.)-{[7-(4-chloro-2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]m- ethyl}amine, (.+-.)-{[7-(5-chloro-2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl- }amine, (.+-.)-{[7-(5-chloro-2-methoxyphenyl)-2,3-dihydro-1-benzofuran-2-y- l]methyl}amine, (.+-.)-[(7-pyridin-3-yl-2,3-dihydro-1-benzofuran-2-yl)methyl]amine, (+)-{[7-pyridin-3-yl-2,3-dihydro-1-benzofuran-2-yl]methyl}amine, (-)-{[7-pyridin-3-yl-2,3-dihydro-1-benzofuran-2-yl]methyl}amine, (.+-.)-{[5-fluoro-7-(2-methoxyphenyl)-2,3-dihydro-1-benzofuran-2-yl]methy- l}amine, (.+-.)-{[5-fluoro-7-(3-fluorophenyl)-2,3-dihydro-1-benzofuran-2-y- l]methyl}amine, (.+-.)-{[5-fluoro-7-(3-methoxyphenyl)-2,3-dihydro-1-benzofuran-2-yl]methy- l}amine, (.+-.)-{[5-fluoro-7-(3-methylphenyl)-2,3-dihydro-1-benzofuran-2-y- l]methyl}amine, (.+-.)-{[5-fluoro-7-(4-fluorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl- }amine, (.+-.)-{[5-fluoro-7-(4-chlorophenyl)-2,3-dihydro-1-benzofuran-2-yl- ]methyl}amine, (.+-.)-{[5-fluoro-7-(4-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl- }amine, (.+-.)-{[5-fluoro-7-(4-methoxyphenyl)-2,3-dihydro-1-benzofuran-2-y- l]methyl}amine, (.+-.)-[(5-fluoro-7-thien-3-yl-2,3-dihydro-1-benzofuran-2-yl)methyl]amine- , (.+-.)-{[5-fluoro-7-(3-furyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}amine- , (.+-.)-[(5-fluoro-7-pyridin-2-yl-2,3-dihydro-1-benzofuran-2-yl)methyl]am- ine, (.+-.)-[(5-fluoro-7-pyridin-3-yl-2,3-dihydro-1-benzofuran-2-yl)methyl- ]amine, (-)-[(5-fluoro-7-pyridin-3-yl-2,3-dihydro-1-benzofuran-2-yl)methyl- ]amine, (+)-{[5-fluoro-7-pyridin-3-yl-2,3-dihydro-1-benzofuran-2-yl]methyl- }amine, (.+-.)-[(5-fluoro-7-pyridin-4-yl-2,3-dihydro-1-benzofuran-2-yl)met- hyl]amine, (.+-.)-[(5-fluoro-7-pyrimidin-5-yl-2,3-dihydro-1-benzofuran-2-y- l)methyl]amine, (.+-.)-{[7-(2,3-dichlorophenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]me- thyl}amine, (.+-.)-{[7-(2,3-dimethoxyphenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]m- ethyl}amine, (-)-{[7-(2,3-dimethoxyphenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]meth- yl}amine, (+)-{[7-(2,3-dimethoxyphenyl)-5-fluoro-2,3-dihydro-1-benzofuran-- 2-yl]methyl}amine, (.+-.)-{[7-(2,4-difluorophenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]me- thyl}amine, (.+-.)-{[7-(2,4-dichlorophenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]me- thyl}amine, (-)-{[5-fluoro-7-(2,4-dichlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methy- l}amine, (+)-{[5-fluoro-7-(2,4-dichlorophenyl)-2,3-dihydro-1-benzofuran-2-- yl]methyl}amine, (.+-.)-{[7-(2,4-dimethoxyphenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]m- ethyl}amine, (.+-.)-{[7-(2,5-difluorophenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]me- thyl}amine, (.+-.)-{[7-(2,5-dichlorophenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]me- thyl}amine, (.+-.)-{[7-(2,5-dimethylphenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]me- thyl}amine, (.+-.)-{[7-(2,5-dimethoxyphenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]m- ethyl}amine, (.+-.)-{[5-fluoro-7-(5-methoxy-2-methylphenyl)-2,3-dihydro-1-benzofuran-2- -yl]methyl}amine, (.+-.)-{[5-fluoro-7-(2-methoxy-5-methylphenyl)-2,3-dihydro-1-benzofuran-2- -yl]methyl}amine, (.+-.)-{[7-(2,6-difluorophenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]me- thyl}amine, (.+-.)-{[7-(2,6-dimethylphenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]me- thyl}amine, (+)-{[7-(2,6-dimethylphenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]methy- l}amine, (-)-{[7-(2,6-dimethylphenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-- yl]methyl}amine, (.+-.)-{[7-(2,6-dichlorophenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]me- thyl}amine, (.+-.)-N-{[7-(2,6-dichlorophenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]- methyl}cyclopropanamine, (.+-.)-1-cyclopropyl-N-{[7-(2,6-dichlorophenyl)-5-fluoro-2,3-dihydro-1-be- nzofuran-2-yl]methyl}methanamine, (.+-.)-N-{[7-(2,6-dichlorophenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]- methyl}cyclobutanamine, (.+-.)-N-{[7-(2,6-dichlorophenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]- methyl}ethanamine, (.+-.)-N-{[7-(2,6-dichlorophenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]- methyl}propan-1-amine, (.+-.)-N-{[7-(2,6-dichlorophenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]- methyl}propan-2-amine, (.+-.)-{[7-(2,6-dichlorophenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]me- thyl}dimethylamine, (.+-.)-1-{[7-(2,6-dichlorophenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]- methyl}piperidine (.+-.)-1-{[7-(2,6-dichlorophenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]- methyl}morpholine (.+-.)-1-{[7-(2,6-dichlorophenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]- methyl}pyrrolidine (.+-.)-{[5-chloro-7-(2-fluorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl- }amine, (.+-.)-{[5-chloro-7-(2-methoxyphenyl)-2,3-dihydro-1-benzofuran-2-y- l]methyl}amine, (.+-.)-{[5-chloro-7-(3-furyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}amine, (.+-.)-{[5-chloro-7-(2,3-difluorophenyl)-2,3-dihydro-1-benzofuran-2-yl]me- thyl}amine, (-)-{[5-chloro-7-(2,3-difluorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methy- l}amine, (+)-{[5-chloro-7-(2,3-difluorophenyl)-2,3-dihydro-1-benzofuran-2-- yl]methyl}amine, (.+-.)-{[5-chloro-7-(2,3-dichlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]me- thyl}amine, (.+-.)-{[5-chloro-7-(2,3-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]me- thyl}amine, (.+-.)-{[5-chloro-7-(2,3-dimethoxyphenyl)-2,3-dihydro-1-benzofuran-2-yl]m- ethyl}amine, (.+-.)-{[5-chloro-7-(2,4-difluorophenyl)-2,3-dihydro-1-benzofuran-2-yl]me- thyl}amine, (.+-.)-{[5-chloro-7-(2,4-dichlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]me- thyl}amine, (-)-{[5-chloro-7-(2,4-dichlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methy- l}amine, (+)-{[5-chloro-7-(2,4-dichlorophenyl)-2,3-dihydro-1-benzofuran-2-- yl]methyl}amine, (.+-.)-{[5-chloro-7-(2,4-dimethoxyphenyl)-2,3-dihydro-1-benzofuran-2-yl]m- ethyl}amine, (.+-.)-{[5-chloro-7-(2,5-difluorophenyl)-2,3-dihydro-1-benzofuran-2-yl]me- thyl}amine, (.+-.)-{[5-chloro-7-(2,5-dichlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]me- thyl}amine, (.+-.)-{[5-chloro-7-(5-chloro-2-methoxyphenyl)-2,3-dihydro-1-benzofuran-2- -yl]methyl}amine, (.+-.)-{[5-chloro-7-(3,4-difluorophenyl)-2,3-dihydro-1-benzofuran-2-yl]me- thyl}amine, (.+-.)-{[5-chloro-7-(3-chloro-4-fluorophenyl)-2,3-dihydro-1-benzofuran-2-- yl]methyl}amine, (.+-.)-{[5-chloro-7-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]me- thyl}amine, (-)-{[5-chloro-7-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methy- l}amine, (+)-{[5-chloro-7-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-- yl]methyl}amine, (.+-.)-{[5-chloro-7-(2,6-dichlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]me- thyl}amine, (+)-{[5-chloro-7-(2,6-dichlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methy- l}amine, (-)-{[5-chloro-7-(2,6-dichlorophenyl)-2,3-dihydro-1-benzofuran-2-- yl]methyl}amine, (.+-.)-{[(5-chloro-7-pyridin-3-yl-2,3-dihydro-1-benzofuran-2-yl)methyl]am- ine, (.+-.)-N-{[5-chloro-7-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2- -yl]methyl}cyclopropanamine, (.+-.)-N-{[5-chloro-7-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]- methyl}(cyclopropylmethyl)amine, (.+-.)-N-{[5-chloro-7-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]- methyl}cyclobutanamine, (.+-.)-N-{[5-chloro-7-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]- methyl}ethanamine, (.+-.)-N-{[5-chloro-7-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]- methyl}propan-2-amine, (.+-.)-{[5-chloro-7-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]me- thyl}dimethylamine, (.+-.)-1-{[5-chloro-7-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]- methyl}piperidine (.+-.)-4-{[5-chloro-7-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]- methyl}morpholine (.+-.)-4-{[5-chloro-7-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]- methyl}thiomorpholine (.+-.)-N-{[5-chloro-7-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]- methyl}propan-1-amine, (.+-.)-1-{[5-chloro-7-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]- methyl}piperazine (.+-.)-1-{[5-chloro-7-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]- methyl}pyrrolidine (.+-.)-{[7-(2-methylphenyl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methyl- }amine, (.+-.)-{[7-(2-fluorophenyl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl- ]methyl}amine, (.+-.)-{[7-(2-methoxyphenyl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methy- l}amine, (.+-.)-{[7-(2-chlorophenyl)-5-methyl-2,3-dihydro-1-benzofuran-2-y- l]methyl}amine, (.+-.)-({5-methyl-7-[2-(trifluoromethyl)phenyl]-2,3-dihydro-1-benzofuran-- 2-yl}methyl)amine, (.+-.)-{[7-(3-chlorophenyl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methyl- }amine, (.+-.)-{[7-(3-methylphenyl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl- ]methyl}amine, (.+-.)-{[7-(4-methylphenyl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methyl- }amine, (.+-.)-{[7-(4-fluorophenyl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl- ]methyl}amine, (.+-.)-{[7-(4-chlorophenyl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methyl- }amine, (.+-.)-{[7-(4-methoxyphenyl)-5-methyl-2,3-dihydro-1-benzofuran-2-y- l]methyl}amine, (.+-.)-{[7-(2,3-dimethoxyphenyl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]m- ethyl}amine, (-)-{[7-(2,3-dimethoxyphenyl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]meth- yl}amine, (+)-{[7-(2,3-dimethoxyphenyl)-5-methyl-2,3-dihydro-1-benzofuran-- 2-yl]methyl}amine, (.+-.)-{[7-(2,4-dichlorophenyl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]me- thyl}amine, (-)-{[7-(2,4-dichlorophenyl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]methy- l}amine, (+)-{[7-(2,4-dichlorophenyl)-5-methyl-2,3-dihydro-1-benzofuran-2-- yl]methyl}amine, (.+-.)-{[7-(2,5-dichlorophenyl)-5-methyl-2,3-dihydro-1-benzofuran-2-yl]me- thyl}amine, (.+-.)-{[7-(2,6-d