IP Library Granted Patent US 9,051,280
Granted Patent B2
US 9,051,280 · App. 13/546,434 · Granted Jun 9, 2015

Tetraline and indane derivatives, pharmaceutical compositions containing them, and their use in therapy

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 9,051,280
App. No.
13/546,434
Granted
Jun 9, 2015
Kind
B2
Abstract

The present invention relates to tetraline and indane derivatives of the formula (I) or a physiologically tolerated salt thereof. The invention relates to pharmaceutical compositions comprising such tetraline and indane derivatives, and the use of such tetraline and indane derivatives for therapeutic purposes. The tetraline and indane derivatives are GlyT1 inhibitors.

Claims (298)

1. A compound of formula (I)

wherein

A is a 5- or 6-membered ring;

R is R 1 —W-A 1 -Q-Y-A 2 -X 1 —;

R 1 is hydrogen, C 1 -C 6 -alkyl, C 3 -C 12 -cycloalkyl-C 1 -C 4 -alkyl, halogenated C 1 -C 6 -alkyl, tri-(C 1 -C 4 -alkyl)-silyl-C 1 -C 4 -alkyl, hydroxy-C 1 -C 4 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, amino-C 1 -C 4 alkyl, C 1 -C 6 -alkylamino-C 1 -C 4 -alkyl, di-C 1 -C 6 -alkylamino-C 1 -C 4 -alkyl, C 1 -C 6 -alkylcarbonylamino-C 1 -C 4 -alkyl, C 1 -C 6 -alkyloxycarbonylamino-C 1 -C 4 -alkyl, C 1 -C 6 -alkylaminocarbonylamino-C 1 -C 4 -alkyl, di-C 1 -C 6 -alkylaminocarbonylamino-C 1 -C 4 -alkyl, C 1 -C 6 -alkylsulfonylamino-C 1 -C 4 -alkyl, (optionally substituted C 6 -C 12 -aryl-C 1 -C 6 -alkyl)amino-C 1 -C 4 -alkyl, optionally substituted C 6 -C 12 -aryl-C 1 -C 4 -alkyl, optionally substituted C 3 -C 12 -heterocyclyl-C 1 -C 4 -alkyl, C 3 -C 12 -cycloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, halogenated C 1 -C 6 -alkoxycarbonyl, C 6 -C 12 -aryloxycarbonyl, aminocarbonyl, C 1 -C 6 -alkylaminocarbonyl, (halogenated C 1 -C 4 -alkyl)aminocarbonyl, C 6 -C 12 -arylaminocarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, optionally substituted C 6 -C 12 -aryl, hydroxy, C 1 -C 6 -alkoxy, halogenated C 1 -C 6 -alkoxy, C 1 -C 6 -hydroxyalkoxy, C 1 -C 6 -alkoxy-C 1 -C 4 -alkoxy, amino-C 1 -C 4 -alkoxy, C 1 -C 6 -alkylamino-C 1 -C 4 -alkoxy, di-C 1 -C 6 -alkylamino-C 1 -C 4 -alkoxy, C 1 -C 6 -alkylcarbonylamino-C 1 -C 4 -alkoxy, C 6 -C 12 -arylcarbonylamino-C 1 -C 4 -alkoxy, C 1 -C 6 -alkoxycarbonylamino-C 1 -C 4 -alkoxy, C 6 -C 12 -aryl-C 1 -C 4 -alkoxy, C 1 -C 6 -alkylsulfonylamino-C 1 -C 4 -alkoxy, (halogenated C 1 -C 6 -alkyl)sulfonylamino-C 1 -C 4 -alkoxy, C 6 -C 12 -arylsulfonylamino-C 1 -C 4 -alkoxy, (C 6 -C 12 -aryl-C 1 -C 6 -alkyl)sulfonylamino-C 1 -C 4 -alkoxy, C 3 -C 12 -heterocyclylsulfonylamino-C 1 -C 4 -alkoxy, C 3 -C 12 -heterocyclyl-C 1 -C 4 -alkoxy, C 6 -C 12 -aryloxy, C 3 -C 12 -heterocyclyloxy, C 1 -C 6 -alkylthio, halogenated C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino, (halogenated C 1 -C 6 -alkyl)amino, di-C 1 -C 6 -alkylamino, di-(halogenated C 1 -C 6 -alkyl)amino, C 1 -C 6 -alkylcarbonylamino, (halogenated C 1 -C 6 -alkyl)carbonylamino, C 6 -C 12 -arylcarbonylamino, C 1 -C 6 -alkylsulfonylamino, (halogenated C 1 -C 6 -alkyl)sulfonylamino, C 6 -C 12 -arylsulfonylamino, or optionally substituted C 3 -C 12 -heterocyclyl;

W is —NR 8 — or a bond;

A 1 is optionally substituted C 1 -C 4 alkylene or a bond;

Q is —S(O) 2 — or —C(O)—;

Y is —NR 9 — or a bond;

A 2 is optionally substituted C 1 -C 4 -alkylene, C 1 -C 4 -alkylene-CO—, —CO—C 1 -C 4 -alkylene, C 1 -C 4 -alkylene-O—C 1 -C 4 -alkylene, C 1 -C 4 -alkylene-NR 10 —C 1 -C 4 -alkylene, optionally substituted C 2 -C 4 -alkenylene, optionally substituted C 2 -C 4 -alkynylene, optionally substituted C 6 -C 12 arylene, optionally substituted C 6 -C 12 -heteroarylene, or a bond;

X 1 is —O—, —NR 11 —, —S—, optionally substituted C 1 -C 4 -alkylene, optionally substituted C 2 -C 4 -alkenylene, or optionally substituted C 2 -C 4 -alkynylene;

R 2 is hydrogen, halogen, C 1 -C 6 -alkyl, halogenated C 1 -C 4 -alkyl, hydroxy-C 1 -C 4 -alkyl, —CN, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, optionally substituted C 6 -C 12 -aryl, hydroxy, C 1 -C 6 -alkoxy, halogenated C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkenyloxy, C 6 -C 12 -aryl-C 1 -C 4 -alkoxy, C 1 -C 6 -alkylcarbonyloxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, aminosulfonyl, amino, C 1 -C 6 -alkylamino, C 2 -C 6 -alkenylamino, nitro or optionally substituted C 3 -C 12 -heterocyclyl, or two radicals R 2 together with the ring atoms of A to which they are bound form a 5- or 6 membered ring;

R 3 is hydrogen, halogen, C 1 -C 6 -alkyl, or C 1 -C 6 -alkoxy, or two radicals R 3 together with the carbon atom to which they are attached form a carbonyl group;

Y 1 is optionally substituted C 1 -C 4 -alkylene;

R 4a is hydrogen, C 1 -C 6 -alkyl, C 3 -C 12 -cycloalkyl-C 1 -C 4 -alkyl, halogenated C 1 -C 4 -alkyl, hydroxy-C 1 -C 4 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, amino-C 1 -C 4 -alkyl, CH 2 CN, C 6 -C 12 -aryl-C 1 -C 4 -alkyl, C 3 -C 12 -cycloalkyl, —CHO, C 1 -C 4 -alkylcarbonyl, (halogenated C 1 -C 4 -alkyl)carbonyl, C 6 -C 12 -arylcarbonyl, C 1 -C 4 -alkoxycarbonyl, C 6 -C 12 -aryloxycarbonyl, C 1 -C 6 -alkylaminocarbonyl, C 2 -C 6 -alkenyl, —C(═NH)NH 2 , —C(═NH)NHCN, C 1 -C 6 -alkylsulfonyl, C 6 -C 12 -arylsulfonyl, amino, —NO, or C 3 -C 12 -heterocyclyl; or

R 4a is optionally substituted C 1 -C 4 -alkylene that is bound to a carbon atom in Y 1 ;

R 4b is hydrogen, C 1 -C 6 -alkyl, halogenated C 1 -C 4 -alkyl, hydroxy-C 1 -C 4 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, amino-C 1 -C 4 -alkyl, CH 2 CN, —CHO, C 1 -C 4 -alkylcarbonyl, (halogenated C 1 -C 4 -alkyl)carbonyl, C 6 -C 12 -arylcarbonyl, C 1 -C 4 -alkoxycarbonyl, C 6 -C 12 -aryloxycarbonyl, C 1 -C 6 -alkylaminocarbonyl, C 2 -C 6 -alkenyl, —C(═NH)NH 2 , —C(═NH)NHCN, C 1 -C 6 -alkylsulfonyl, C 6 -C 12 -arylsulfonyl, amino, —NO, or C 3 -C 12 -heterocyclyl; or

R 4a , R 4b

together are optionally substituted C 1 -C 6 -alkylene, wherein one —CH 2 — of C 1 -C 4 -alkylene may be replaced by an oxygen atom or —NR 16 ;

X 2 is —O—, —NR 6 —, —S—, >CR 12a R 12b , or a bond;

X 3 is —O—, —NR 7 —, —S—, >CR 13a R 13b , or a bond;

R 5 is optionally substituted C 6 -C 12 -aryl, optionally substituted C 3 -C 12 -cycloalkyl, or optionally substituted C 3 -C 12 -heterocyclyl;

n is 0, 1, or 2;

R 6 is hydrogen or C 1 -C 6 -alkyl;

R 7 is hydrogen or C 1 -C 6 -alkyl;

R 8 is hydrogen or C 1 -C 6 -alkyl;

R 9 is hydrogen, C 1 -C 6 -alkyl, C 3 -C 12 -cycloalkyl, amino-C 1 -C 6 -alkyl, optionally substituted C 6 -C 12 -aryl-C 1 -C 4 -alkyl, or C 3 -C 12 -heterocyclyl; or

R 9 , R 1

together are C 1 -C 4 -alkylene; or

R 9 is C 1 -C 4 -alkylene that is bound to a carbon atom in A 2 and A 2 is C 1 -C 4 -alkylene, or to a carbon atom in X 1 and X 1 is C 1 -C 4 -alkylene;

R 10 is hydrogen, C 1 -C 6 -alkyl, or C 1 -C 6 -alkylsulfonyl;

R 11 is hydrogen or C 1 -C 6 -alkyl; or

R 9 , R 11

together are C 1 -C 4 -alkylene;

R 12a is hydrogen, optionally substituted C 1 -C 6 -alkyl, C 1 -C 6 -alkylamino-C 1 -C 4 -alkyl, di-C 1 -C 6 -alkylamino-C 1 -C 4 -alkyl, C 3 -C 12 -heterocyclyl-C 1 -C 6 -alkyl, optionally substituted C 6 -C 12 -aryl, or hydroxy;

R 12b is hydrogen or C 1 -C 6 -alkyl; or

R 12a , R 12b

together are carbonyl or optionally substituted C 1 -C 4 -alkylene, wherein one —CH 2 — of C 1 -C 4 -alkylene may be replaced by an oxygen atom or —NR 14 —;

R 13a is hydrogen, optionally substituted C 1 -C 6 -alkyl, C 1 -C 6 -alkylamino-C 1 -C 4 -alkyl, di-C 1 -C 6 -alkylamino-C 1 -C 4 -alkyl, C 3 -C 12 -heterocyclyl-C 1 -C 6 -alkyl, optionally substituted C 6 -C 12 -aryl, or hydroxy;

R 13b is hydrogen or C 1 -C 6 -alkyl; or

R 13a , R 13b

together are carbonyl or optionally substituted C 1 -C 4 -alkylene, wherein one —CH 2 — of C 1 -C 4 -alkylene may be replaced by an oxygen atom or —NR 15 —;

R 14 is hydrogen or C 1 -C 6 -alkyl;

R 15 is hydrogen or C 1 -C 6 -alkyl; and

R 16 is hydrogen or C 1 -C 6 -alkyl;

or a physiologically tolerated salt thereof.

2. A compound of claim 1 , wherein A is a benzene ring or a ring selected from the group consisting of the following 5- or 6-membered heterocyclic rings:

3. A compound of claim 1 , wherein —Y-A 2 -X 1 — comprises at least 2, 3 or 4 atoms in the main chain.

4. A compound of claim 1 , wherein R 1 is C 1 -C 6 -alkyl, C 3 -C 12 -cycloalkyl-C 1 -C 4 -alkyl, C 3 -C 12 -cycloalkyl, or optionally substituted C 3 -C 12 -heterocyclyl.

5. A compound of claim 1 , wherein A 1 is a bond.

6. A compound of claim 1 , wherein W is a bond and Y is a bond, or W is a bond and Y is —NR 9 —.

7. A compound of claim 1 , wherein X 1 is —O— and A 2 is C 1 -C 4 -alkylene, or X 1 is C 1 -C 4 -alkylene and A 2 is a bond.

8. A compound of claim 1 , wherein R 1 —W-A 1 -Q-Y-A 2 -X 1 — is R 1 —S(O) 2 —NR 9 -A 2 -X 1 — or R 1 —S(O) 2 —X 1 —.

9. A compound of claim 1 , having the formula

wherein R 1 , W, A 1 , Q, Y, A 2 , X 1 , R 2 , R 3 , Y 1 , R 4a , R 4b , X 2 , X 3 , R 5 , n are as defined in claim 1 .

10. A compound of claim 1 , wherein Y 1 is methylene or 1,2-ethylene.

11. A compound of claim 1 , wherein R 4a is C 1 -C 6 -alkyl, C 3 -C 12 -cycloalkyl, or C 3 -C 12 -heterocyclyl, or R 4a is C 1 -C 4 -alkylene that is bound to a carbon atom in Y 1 .

12. A compound of claim 1 , wherein R 4b is hydrogen or C 1 -C 6 -alkyl.

13. A compound of claim 1 , wherein R 4a , R 4b together are optionally substituted C 1 -C 6 -alkylene, wherein one —CH 2 — of C 1 -C 4 -alkylene may be replaced by an oxygen atom.

14. A compound of claim 1 , wherein X 2 is CR 12a R 12b and X 3 is a bond.

15. A compound of claim 1 , wherein R 12a is hydrogen or C 1 -C 6 -alkyl, and R 12b is hydrogen or C 1 -C 6 -alkyl, or R 12a , R 12b together are optionally substituted C 1 -C 4 -alkylene.

16. A compound of claim 1 , having the formula

wherein A, R, R 2 , R 3 , Y 1 , R 4a , R 4b , X 2 , X 3 , n are as defined in claims 1 ; and

R 17a , R 17b , R 17c , R 17d , R 17e independently are hydrogen, halogen, or halogenated C 1 -C 6 -alkyl.

17. A compound of claim 1 , wherein

A is a benzene ring;

R is R 1 —W-A 1 -Q-Y-A 2 -X 1 —;

R 1 is C 1 -C 6 -alkyl, C 3 -C 12 -cycloalkyl-C 1 -C 4 -alkyl, C 3 -C 12 -cycloalkyl, or optionally substituted C 3 -C 12 -heterocyclyl;

W is a bond;

A 1 is a bond;

Q is —S(O) 2 —;

Y is —NR 9 — or a bond;

A 2 is C 1 -C 4 -alkylene or a bond;

X 1 is —O— or C 1 -C 4 -alkylene;

R 2 is hydrogen or halogen;

R 3 is hydrogen;

Y 1 is optionally substituted C 1 -C 4 -alkylene;

R 4a is hydrogen, C 1 -C 6 -alkyl, C 3 -C 12 -cycloalkyl, or C 3 -C 12 -heterocyclyl; or

R 4a is optionally substituted C 1 -C 4 -alkylene that is bound to a carbon atom in Y 1 ;

R 4b is hydrogen; or

R 4a , R 4b

together are C 1 -C 6 -alkylene, wherein one —CH 2 — of C 1 -C 4 -alkylene may be replaced by an oxygen atom;

X 2 is CR 12a R 12b ;

X 3 is a bond;

R 5 is optionally substituted phenyl;

n is 0 or 1;

R 9 is hydrogen; or

R 9 is C 1 -C 4 -alkylene that is bound to a carbon atom in X 1 and X 1 is C 1 -C 4 -alkylene;

R 12a is hydrogen; and

R 12b is hydrogen; or

R 12a , R 12b

together are C 1 -C 4 -alkylene.

18. A compound of claim 1 , which is selected from the group consisting of:

N-[2-[3-benzyl-2-(methylaminomethyl)indan-5-yl]oxyethyl]-1-cyclopropyl-methanesulfonamide;

N-[2-[3-benzyl-2-(methylaminomethyl)indan-5-yl]oxyethyl]cyclobutanesulfonamide;

N-[2-[3-benzyl-2-(methylaminomethyl)indan-5-yl]oxyethyl]-1-methyl-imidazole-4-sulfonamide;

N-[2-[3-benzyl-2-(methylaminomethyl)indan-5-yl]oxyethyl]-1-methyl-pyrazole-4-sulfonamide;

N-[[3-benzyl-2-(methylaminomethyl)indan-5-yl]-methyl]-1-cyclopropyl-methanesulfonamide;

N-[2-[3-benzyl-2-(methylaminomethyl)indan-5-yl]ethyl]-1-cyclopropyl-methanesulfonamide;

N-[[3-benzyl-2-(methylaminomethyl)indan-5-yl]methyl]cyclobutanesulfonamide;

N-[2-[3-benzyl-2-(methylaminomethyl)indan-5-yl]ethyl]cyclobutanesulfonamide;

N-[[3-benzyl-2-(methylaminomethyl)indan-5yl]methyl]-1-methyl-imidazole-4-sulfonamide;

N-[2-[3-benzyl-2-(methylaminomethyl)indan-5-yl]ethyl]-1-methyl-imidazole-4-sulfonamide;

N-[[3-benzyl-2-(methylaminomethyl)indan-5yl]methyl]-1-methyl-pyrazole-4-sulfonamide;

N-[2-[3-benzyl-2-(methylaminomethyl)indan-5yl]ethyl]-1-methyl-pyrazole-4-sulfonamide;

N-[2-[3-benzyl-6-fluoro-2-(methylaminomethyl)indan-5-yl]oxyethyl]-1-cyclopropyl-methanesulfonamide;

N-[2-[3-benzyl-6-fluoro-2-(methylaminomethyl)indan-5-yl]oxyethyl]-cyclobutanesulfonamide;

N-[2-[3-benzyl-6-fluoro-2-(methylaminomethyl)indan-5-yl]oxyethyl]-1-methyl-imidazole-4-sulfonamide;

N-[2-[3-benzyl-6-fluoro-2-(methylaminomethyl)indan-5-yl]oxyethyl]-1-methyl-pyrazole-4-sulfonamide;

N-[[3-benzyl-6-fluoro-2-(methylaminomethyl)indan-5-yl]methyl]-1-cyclopropyl-methanesulfonamide;

N-[2-[3-benzyl-6-fluoro-2-(methylaminomethyl)indan-5-yl]ethyl]-1-cyclopropyl-methanesulfonamide;

N-[[3-benzyl-6-fluoro-2-(methylaminomethyl)indan-5-yl]methyl]-cyclobutanesulfonamide;

N-[2-[3-benzyl-6-fluoro-2-(methylaminomethyl)indan-5-yl]ethyl]-cyclobutanesulfonamide;

N-[[3-benzyl-6-fluoro-2-(methylaminomethyl)indan-5-yl]methyl]-1-methyl-imidazole-4-sulfonamide;

N-[2-[3-benzyl-6-fluoro-2-(methylaminomethyl)indan-5-yl]ethyl]-1-methyl-imidazole-4-sulfonamide;

N-[[3-benzyl-6-fluoro-2-(methylaminomethyl)indan-5-yl]methyl]-1-methyl-pyrazole-4-sulfonamide;

N-[2-[3-benzyl-6-fluoro-2-(methylaminomethyl)indan-5-yl]ethyl]-1-methyl-pyrazole-4-sulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-3-benzyl-indan-5-yl]oxyethyl]-1-cyclopropyl-methanesulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-3-benzyl-indan-5-yl]oxyethyl]cyclobutanesulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-3-benzyl-indan-5-yl]oxyethyl]-1-methyl-imidazole-4-sulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-3-benzyl-indan-5-yl]oxyethyl]-1-methyl-pyrazole-4-sulfonamide;

N-[[2-(azetidin-1-ylmethyl)-3-benzyl-indan-5-yl]methyl]-1-cyclopropyl-methanesulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-3-benzyl-indan-5-yl]ethyl]-1-cyclopropyl-methanesulfonamide;

N-[[2-(azetidin-1-ylmethyl)-3-benzyl-indan-5-yl]methyl]cyclobutanesulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-3-benzyl-indan-5-yl]ethyl]cyclobutanesulfonamide;

N-[[2-(azetidin-1-ylmethyl)-3-benzyl-indan-5-yl]methyl]-1-methyl-imidazole-4-sulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-3-benzyl-indan-5-yl]ethyl]-1-methyl-imidazole-4-sulfonamide;

N-[[2-(azetidin-1-ylmethyl)-3-benzyl-indan-5-yl]methyl]-1-methyl-pyrazole-4-sulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-3-benzyl-indan-5-yl]ethyl]-1-methyl-pyrazole-4-sulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-3-benzyl-6-fluoro-indan-5-yl]oxyethyl]-1-cyclopropyl-methanesulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-3-benzyl-6-fluoro-indan-5-yl]oxyethyl]-cyclobutanesulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-3-benzyl-6-fluoro-indan-5-yl]oxyethyl]-1-methyl-imidazole-4-sulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-3-benzyl-6-fluoro-indan-5-yl]oxyethyl]-1-methyl-pyrazole-4-sulfonamide;

N-[[2-(azetidin-1-ylmethyl)-3-benzyl-6-fluoro-indan-5-yl]methyl]-1-cyclopropyl-methanesulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-3-benzyl-6-fluoro-indan-5-yl]ethyl]-1-cyclopropyl-methanesulfonamide;

N-[[2-(azetidin-1-ylmethyl)-3-benzyl-6-fluoro-indan-5-yl]methyl]cyclobutanesulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-3-benzyl-6-fluoro-indan-5-yl]ethyl]cyclobutanesulfonamide;

N-[[2-(azetidin-1-ylmethyl)-3-benzyl-6-fluoro-indan-5-yl]methyl]-1-methyl-imidazole-4-sulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-3-benzyl-6-fluoro-indan-5-yl]ethyl]-1-methyl-imidazole-4-sulfonamide;

N-[[2-(azetidin-1-ylmethyl)-3-benzyl-6-fluoro-indan-5-yl]methyl]-1-methyl-pyrazole-4-sulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-3-benzyl-6-fluoro-indan-5-yl]ethyl]-1-methyl-pyrazole-4-sulfonamide;

1-cyclopropyl-N-[2-[3-[(3-fluorophenyl)methyl]-2-(methylaminomethyl)indan-5-yl]oxyethyl]methanesulfonamide;

N-[2-[3-[(3-fluorophenyl)methyl]-2-(methylaminomethyl)indan-5-yl]oxyethyl]-cyclobutanesulfonamide;

N-[2-[3-[(3-fluorophenyl)methyl]-2-(methylaminomethyl)indan-5-yl]oxyethyl]-1-methyl-imidazole-4-sulfonamide;

N-[2-[3-[(3-fluorophenyl)methyl]-2-(methylaminomethyl)indan-5-yl]oxyethyl]-1-methyl-pyrazole-4-sulfonamide;

1-cyclopropyl-N-[[3-[(3-fluorophenyl)methyl]-2-(methylaminomethyl)indan-5-yl]methyl]methanesulfonamide;

1-cyclopropyl-N-[2-[3-[(3-fluorophenyl)methyl]-2-(methylaminomethyl)indan-5-yl]ethyl]methanesulfonamide;

N-[[3-[(3-fluorophenyl)methyl]-2-(methylaminomethyl)indan-5-yl]methyl]-cyclobutanesulfonamide;

N-[2-[3-[(3-fluorophenyl)methyl]-2-(methylaminomethyl)indan-5-yl]ethyl]cyclobutanesulfonamide;

N-[[3-[(3-fluorophenyl)methyl]-2-(methylaminomethyl)indan-5-yl]methyl]-1-methyl-imidazole-4-sulfonamide;

N-[2-[3-[(3-fluorophenyl)methyl]-2-(methylaminomethyl)indan-5-yl]ethyl]-1-methyl-imidazole-4-sulfonamide;

N-[[3-[(3-fluorophenyl)methyl]-2-(methylaminomethyl)indan-5-yl]methyl]-1-methyl-pyrazole-4-sulfonamide;

N-[2-[3-[(3-fluorophenyl)methyl]-2-(methylaminomethyl)indan-5-yl]ethyl]-1-methyl-pyrazole-4-sulfonamide;

1-cyclopropyl-N-[2-[6-fluoro-3-[(3-fluorophenyl)methyl]-2-(methylaminomethyl)indan-5-yl]oxyethyl]methanesulfonamide;

N-[2-[6-fluoro-3-[(3-fluorophenyl)methyl]-2-(methylaminomethyl)indan-5-yl]oxyethyl]cyclobutanesulfonamide;

N-[2-[6-fluoro-3-[(3-fluorophenyl)methyl]-2-(methylaminomethyl)indan-5-yl]oxyethyl]-1-methyl-imidazole-4-sulfonamide;

N-[2-[6-fluoro-3-[(3-fluorophenyl)methyl]-2-(methylaminomethyl)indan-5-yl]oxyethyl]-1-methyl-pyrazole-4-sulfonamide;

1-cyclopropyl-N-[[6-fluoro-3-[(3-fluorophenyl)methyl]-2-(methylaminomethyl)indan-5-yl]methyl]methanesulfonamide;

1-cyclopropyl-N-[2-[6-fluoro-3-[(3-fluorophenyl)methyl]-2-(methylaminomethyl)indan-5-yl]ethyl]methanesulfonamide;

N-[[6-fluoro-3-[(3-fluorophenyl)methyl]-2-(methylaminomethyl)indan-5-yl]methyl]cyclobutanesulfonamide;

N-[2-[6-fluoro-3-[(3-fluorophenyl)methyl]-2-(methylaminomethyl)indan-5-yl]ethyl]cyclobutanesulfonamide;

N-[[6-fluoro-3-[(3-fluorophenyl)methyl]-2-(methylaminomethyl)indan-5-yl]methyl]-1-methyl-imidazole-4-sulfonamide;

N-[2-[6-fluoro-3-[(3-fluorophenyl)methyl]-2-(methylaminomethyl)indan-5-yl]ethyl]-1-methyl-imidazole-4-sulfonamide;

N-[[6-fluoro-3-[(3-fluorophenyl)methyl]-2-(methylaminomethyl)indan-5-yl]methyl]-1-methyl-pyrazole-4-sulfonamide;

N-[2-[6-fluoro-3-[(3-fluorophenyl)methyl]-2-(methylaminomethyl)indan-5-yl]ethyl]-1-methyl-pyrazole-4-sulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-3-[(3-fluorophenyl)methyl]indan-5-yl]oxyethyl]-1-cyclopropyl-methanesulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-3-[(3-fluorophenyl)methyl]indan-5-yl]oxyethyl]cyclobutanesulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-3-[(3-fluorophenyl)methyl]indan-5-yl]oxyethyl]-1-methyl-imidazole-4-sulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-3-[(3-fluorophenyl)methyl]indan-5-yl]oxyethyl]-1-methyl-pyrazole-4-sulfonamide;

N-[[2-(azetidin-1-ylmethyl)-3-[(3-fluorophenyl)methyl]indan-5-yl]methyl]-1-cyclopropyl-methanesulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-3-[(3-fluorophenyl)methyl]indan-5-yl]ethyl]-1-cyclopropyl-methanesulfonamide;

N-[[2-(azetidin-1-ylmethyl)-3-[(3-fluorophenyl)methyl]indan-5-yl]methyl]cyclobutanesulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-3-[(3-fluorophenyl)methyl]indan-5-yl]ethyl]cyclobutanesulfonamide;

N-[[2-(azetidin-1-ylmethyl)-3-[(3-fluorophenyl)methyl]indan-5-yl]methyl]-1-methyl-imidazole-4-sulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-3-[(3-fluorophenyl)methyl]indan-5-yl]ethyl]-1-methyl-imidazole-4-sulfonamide;

N-[[2-(azetidin-1-ylmethyl)-3-[(3-fluorophenyl)methyl]indan-5-yl]methyl]-1-methyl-pyrazole-4-sulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-3-[(3-fluorophenyl)methyl]indan-5-yl]ethyl]-1-methyl-pyrazole-4-sulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-6-fluoro-3-[(3-fluorophenyl)methyl]indan-5-yl]oxyethyl]-1-cyclopropyl-methanesulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-6-fluoro-3-[(3-fluorophenyl)methyl]indan-5-yl]oxyethyl]cyclobutanesulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-6-fluoro-3-[(3-fluorophenyl)methyl]indan-5-yl]oxyethyl]-1-methyl-imidazole-4-sulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-6-fluoro-3-[(3-fluorophenyl)methyl]indan-5-yl]oxyethyl]-1-methyl-pyrazole-4-sulfonamide;

N-[[2-(azetidin-1-ylmethyl)-6-fluoro-3-[(3-fluorophenyl)methyl]indan-5-yl]methyl]-1-cyclopropyl-methanesulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-6-fluoro-3-[(3-fluorophenyl)methyl]indan-5-yl]ethyl]-1-cyclopropyl-methanesulfonamide;

N-[[2-(azetidin-1-ylmethyl)-6-fluoro-3-[(3-fluorophenyl)methyl]indan-5-yl]methyl]cyclobutanesulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-6-fluoro-3-[(3-fluorophenyl)methyl]indan-5-yl]ethyl]cyclobutanesulfonamide;

N-[[2-(azetidin-1-ylmethyl)-6-fluoro-3-[(3-fluorophenyl)methyl]indan-5-yl]methyl]-1-methyl-imidazole-4-sulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-6-fluoro-3-[(3-fluorophenyl)methyl]indan-5-yl]ethyl]-1-methyl-imidazole-4-sulfonamide;

N-[[2-(azetidin-1-ylmethyl)-6-fluoro-3-[(3-fluorophenyl)methyl]indan-5-yl]methyl]-1-methyl-pyrazole-4-sulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-6-fluoro-3-[(3-fluorophenyl)methyl]indan-5-yl]ethyl]-1-methyl-pyrazole-4-sulfonamide;

N-[2-[3-[(3-chlorophenyl)methyl]-2-(methylaminomethyl)indan-5-yl]oxyethyl]-1-cyclopropyl-methanesulfonamide;

N-[2-[3-[(3-chlorophenyl)methyl]-2-(methylaminomethyl)indan-5-yl]oxyethyl]cyclobutanesulfonamide;

N-[2-[3-[(3-chlorophenyl)methyl]-2-(methylaminomethyl)indan-5-yl]oxyethyl]-1-methyl-imidazole-4-sulfonamide;

N-[2-[3-[(3-chlorophenyl)methyl]-2-(methylaminomethyl)indan-5-yl]oxyethyl]-1-methyl-pyrazole-4-sulfonamide;

N-[2-[3-[(3-chlorophenyl)methyl]-2-(methylaminomethyl)indan-5-yl]oxyethyl]-1-methyl-pyrazole-4-sulfonamide;

N-[2-[3-[(3-chlorophenyl)methyl]-2-(methylaminomethyl)indan-5-yl]ethyl]-1-cyclopropyl-methanesulfonamide;

N-[[3-[(3-chlorophenyl)methyl]-2-(methylaminomethyl)indan-5-yl]methyl]cyclobutanesulfonamide;

N-[2-[3-[(3-chlorophenyl)methyl]-2-(methylaminomethyl)indan-5-yl]ethyl]cyclobutanesulfonamide;

N-[[3-[(3-chlorophenyl)methyl]-2-(methylaminomethyl)indan-5-yl]methyl]-1-methyl-imidazole-4-sulfonamide;

N-[2-[3-[(3-chlorophenyl)methyl]-2-(methylaminomethyl)indan-5-yl]ethyl]-1-methyl-imidazole-4-sulfonamide;

N-[[3-[(3-chlorophenyl)methyl]-2-(methylaminomethyl)indan-5-yl]methyl]-1-methyl-pyrazole-4-sulfonamide;

N-[2-[3-[(3-chlorophenyl)methyl]-2-(methylaminomethyl)indan-5-yl]ethyl]-1-methyl-pyrazole-4-sulfonamide;

N-[2-[3-[(3-chlorophenyl)methyl]-6-fluoro-2-(methylaminomethyl)indan-5-yl]oxyethyl]-1-cyclopropyl-methanesulfonamide;

N-[2-[3-[(3-chlorophenyl)methyl]-6-fluoro-2-(methylaminomethyl)indan-5-yl]oxyethyl]cyclobutanesulfonamide;

N-[2-[3-[(3-chlorophenyl)methyl]-6-fluoro-2-(methylaminomethyl)indan-5-yl]oxyethyl]-1-methyl-imidazole-4-sulfonamide;

N-[2-[3-[(3-chlorophenyl)methyl]-6-fluoro-2-(methylaminomethyl)indan-5-yl]oxyethyl]-1-methyl-pyrazole-4-sulfonamide;

N-[[3-[(3-chlorophenyl)methyl]-6-fluoro-2-(methylaminomethyl)indan-5-yl]methyl]-1-cyclopropyl-methanesulfonamide;

N-[2-[3-[(3-chlorophenyl)methyl]-6-fluoro-2-(methylaminomethyl)indan-5-yl]ethyl]-1-cyclopropyl-methanesulfonamide;

N-[[3-[(3-chlorophenyl)methyl]-6-fluoro-2-(methylaminomethyl)indan-5-yl]methyl]cyclobutanesulfonamide;

N-[2-[3-[(3-chlorophenyl)methyl]-6-fluoro-2-(methylaminomethyl)indan-5-yl]ethyl]cyclobutanesulfonamide;

N-[[3-[(3-chlorophenyl)methyl]-6-fluoro-2-(methylaminomethyl)indan-5-yl]methyl]-1-methyl-imidazole-4-sulfonamide;

N-[2-[3-[(3-chlorophenyl)methyl]-6-fluoro-2-(methylaminomethyl)indan-5-yl]ethyl]-1-methyl-imidazole-4-sulfonamide;

N-[[3-[(3-chlorophenyl)methyl]-6-fluoro-2-(methylaminomethyl)indan-5-yl]methyl]-1-methyl-pyrazole-4-sulfonamide;

N-[2-[3-[(3-chlorophenyl)methyl]-6-fluoro-2-(methylaminomethyl)indan-5-yl]ethyl]-1-methyl-pyrazole-4-sulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-3-[(3-chlorophenyl)methyl]indan-5-yl]oxyethyl]-1-cyclopropyl-methanesulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-3-[(3-chlorophenyl)methyl]indan-5-yl]oxyethyl]cyclobutanesulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-3-[(3-chlorophenyl)methyl]indan-5-yl]oxyethyl]-1-methyl-imidazole-4-sulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-3-[(3-chlorophenyl)methyl]indan-5-yl]oxyethyl]-1-methyl-pyrazole-4-sulfonamide;

N-[[2-(azetidin-1-ylmethyl)-3-[(3-chlorophenyl)methyl]indan-5-yl]methyl]-1-cyclopropyl-methanesulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-3-[(3-chlorophenyl)methyl]indan-5-yl]ethyl]-1-cyclopropyl-methanesulfonamide;

N-[[2-(azetidin-1-ylmethyl)-3-[(3-chlorophenyl)methyl]indan-5-yl]methyl]cyclobutanesulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-3-[(3-chlorophenyl)methyl]indan-5-yl]ethyl]cyclobutanesulfonamide;

N-[[2-(azetidin-1-ylmethyl)-3-[(3-chlorophenyl)methyl]indan-5-yl]methyl]-1-methyl-imidazole-4-sulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-3-[(3-chlorophenyl)methyl]indan-5-yl]ethyl]-1-methyl-imidazole-4-sulfonamide;

N-[[2-(azetidin-1-ylmethyl)-3-[(3-chlorophenyl)methyl]indan-5-yl]methyl]-1-methyl-pyrazole-4-sulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-3-[(3-chlorophenyl)methyl]indan-5-yl]ethyl]-1-methyl-pyrazole-4-sulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-3-[(3-chlorophenyl)methyl]-6-fluoro-indan-5-yl]oxyethyl]-1-cyclopropyl-methanesulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-3-[(3-chlorophenyl)methyl]-6-fluoro-indan-5-yl]oxyethyl]cyclobutanesulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-3-[(3-chlorophenyl)methyl]-6-fluoro-indan-5-yl]oxyethyl]-1-methyl-imidazole-4-sulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-3-[(3-chlorophenyl)methyl]-6-fluoro-indan-5-yl]oxyethyl]-1-methyl-pyrazole-4-sulfonamide;

N-[[2-(azetidin-1-ylmethyl)-3-[(3-chlorophenyl)methyl]-6-fluoro-indan-5-yl]methyl]-1-cyclopropyl-methanesulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-3-[(3-chlorophenyl)methyl]-6-fluoro-indan-5-yl]ethyl]-1-cyclopropyl-methanesulfonamide;

N-[[2-(azetidin-1-ylmethyl)-3-[(3-chlorophenyl)methyl]-6-fluoro-indan-5-yl]methyl]cyclobutanesulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-3-[(3-chlorophenyl)methyl]-6-fluoro-indan-5-yl]ethyl]cyclobutanesulfonamide;

N-[[2-(azetidin-1-ylmethyl)-3-[(3-chlorophenyl)methyl]-6-fluoro-indan-5-yl]methyl]-1-methyl-imidazole-4-sulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-3-[(3-chlorophenyl)methyl]-6-fluoro-indan-5-yl]ethyl]-1-methyl-imidazole-4-sulfonamide;

N-[[2-(azetidin-1-ylmethyl)-3-[(3-chlorophenyl)methyl]-6-fluoro-indan-5-yl]methyl]-1-methyl-pyrazole-4-sulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-3-[(3-chlorophenyl)methyl]-6-fluoro-indan-5-yl]ethyl]-1-methyl-pyrazole-4-sulfonamide;

1-cyclopropyl-N-[2-[2-(methylaminomethyl)-3-[[3-(trifluoromethyl)phenyl]methyl]indan-5-yl]oxyethyl]methanesulfonamide;

N-[2-[2-(methylaminomethyl)-3-[[3-(trifluoromethyl)phenyl]methyl]indan-5-yl]oxyethyl]cyclobutanesulfonamide;

1-methyl-N-[2-[2-(methylaminomethyl)-3-[[3-(trifluoromethyl)phenyl]methyl]indan-5-yl]oxyethyl]imidazole-4-sulfonamide;

1-methyl-N-[2-[2-(methylaminomethyl)-3-[[3-(trifluoromethyl)phenyl]methyl]indan-5-yl]oxyethyl]pyrazole-4-sulfonamide;

1-cyclopropyl-N-[[2-(methylaminomethyl)-3-[[3-(trifluoromethyl)phenyl]methyl]indan-5-yl]methyl]methanesulfonamide;

1-cyclopropyl-N-[2-[2-(methylaminomethyl)-3-[[3-(trifluoromethyl)phenyl]methyl]indan-5-yl]ethyl]methanesulfonamide;

N-[[2-(methylaminomethyl)-3-[[3-(trifluoromethyl)phenyl]methyl]indan-5-yl]methyl]cyclobutanesulfonamide;

N-[2-[2-(methylaminomethyl)-3-[[3-(trifluoromethyl)phenyl]methyl]indan-5-yl]ethyl]cyclobutanesulfonamide;

1-methyl-N-[[2-(methylaminomethyl)-3-[[3-(trifluoromethyl)phenyl]methyl]indan-5-yl]methyl]imidazole-4-sulfonamide;

1-methyl-N-[2-[2-(methylaminomethyl)-3-[[3-(trifluoromethyl)phenyl]methyl]indan-5-yl]ethyl]imidazole-4-sulfonamide;

1-methyl-N-[[2-(methylaminomethyl)-3-[[3-(trifluoromethyl)phenyl]methyl]indan-5-yl]methyl]pyrazole-4-sulfonamide;

1-methyl-N-[2-[2-(methylaminomethyl)-3-[[3-(trifluoromethyl)phenyl]methyl]indan-5-yl]ethyl]pyrazole-4-sulfonamide;

1-cyclopropyl-N-[2-[6-fluoro-2-(methylaminomethyl)-3-[[3-(trifluoromethyl)phenyl]methyl]indan-5-yl]oxyethyl]methanesulfonamide;

N-[2-[6-fluoro-2-(methylaminomethyl)-3-[[3-(trifluoromethyl)phenyl]methyl]indan-5-yl]oxyethyl]cyclobutanesulfonamide;

N-[2-[6-fluoro-2-(methylaminomethyl)-3-[[3-(trifluoromethyl)phenyl]methyl]indan-5-yl]oxyethyl]-1-methyl-imidazole-4-sulfonamide;

N-[2-[6-fluoro-2-(methylaminomethyl)-3-[[3-(trifluoromethyl)phenyl]methyl]indan-5-yl]oxyethyl]-1-methyl-pyrazole-4-sulfonamide;

1-cyclopropyl-N-[[6-fluoro-2-(methylaminomethyl)-3-[[3-(trifluoromethyl)phenyl]methyl]indan-5-yl]methyl]methanesulfonamide;

1-cyclopropyl-N-[2-[6-fluoro-2-(methylaminomethyl)-3-[[3-(trifluoromethyl)phenyl]methyl]indan-5-yl]ethyl]methanesulfonamide;

N-[[6-fluoro-2-(methylaminomethyl)-3-[[3-(trifluoromethyl)phenyl]methyl]indan-5-yl]methyl]cyclobutanesulfonamide;

N-[2-[6-fluoro-2-(methylaminomethyl)-3-[[3-(trifluoromethyl)phenyl]methyl]indan-5-yl]ethyl]cyclobutanesulfonamide;

N-[[6-fluoro-2-(methylaminomethyl)-3-[[3-(trifluoromethyl)phenyl]methyl]indan-5-yl]methyl]-1-methyl-imidazole-4-sulfonamide;

N-[2-[6-fluoro-2-(methylaminomethyl)-3-[[3-(trifluoromethyl)phenyl]methyl]indan-5-yl]ethyl]-1-methyl-imidazole-4-sulfonamide;

N-[[6-fluoro-2-(methylaminomethyl)-3-[[3-(trifluoromethyl)phenyl]methyl]indan-5-yl]methyl]-1-methyl-pyrazole-4-sulfonamide;

N-[2-[6-fluoro-2-(methylaminomethyl)-3-[[3-(trifluoromethyl)phenyl]methyl]indan-5-yl]ethyl]-1-methyl-pyrazole-4-sulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-3-[[3-(trifluoromethyl)phenyl]methyl]indan-5-yl]oxyethyl]-1-cyclopropyl-methanesulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-3-[[3-(trifluoromethyl)phenyl]methyl]indan-5-yl]oxyethyl]cyclobutanesulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-3-[[3-(trifluoromethyl)phenyl]methyl]indan-5-yl]oxyethyl]-1-methyl-imidazole-4-sulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-3-[[3-(trifluoromethyl)phenyl]methyl]indan-5-yl]oxyethyl]-1-methyl-pyrazole-4-sulfonamide;

N-[[2-(azetidin-1-ylmethyl)-3-[[3-(trifluoromethyl)phenyl]methyl]indan-5-yl]methyl]-1-cyclopropyl-methanesulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-3-[[3-(trifluoromethyl)phenyl]methyl]indan-5-yl]ethyl]-1-cyclopropyl-methanesulfonamide;

N-[[2-(azetidin-1-ylmethyl)-3-[[3-(trifluoromethyl)phenyl]methyl]indan-5-yl]methyl]cyclobutanesulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-3-[[3-(trifluoromethyl)phenyl]methyl]indan-5-yl]ethyl]cyclobutanesulfonamide;

N-[[2-(azetidin-1-ylmethyl)-3-[[3-(trifluoromethyl)phenyl]methyl]indan-5-yl]methyl]-1-methyl-imidazole-4-sulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-3-[[3-(trifluoromethyl)phenyl]methyl]indan-5-yl]ethyl]-1-methyl-imidazole-4-sulfonamide;

N-[[2-(azetidin-1-ylmethyl)-3-[[3-(trifluoromethyl)phenyl]methyl]indan-5-yl]methyl]-1-methyl-pyrazole-4-sulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-3-[[3-(trifluoromethyl)phenyl]methyl]indan-5-yl]ethyl]-1-methyl-pyrazole-4-sulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-6-fluoro-3-[[3-(trifluoromethyl)phenyl]methyl]indan-5-yl]oxyethyl]-1-cyclopropyl-methanesulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-6-fluoro-3-[[3-(trifluoromethyl)phenyl]methyl]indan-5-yl]oxyethyl]cyclobutanesulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-6-fluoro-3-[[3-(trifluoromethyl)phenyl]methyl]indan-5-yl]oxyethyl]-1-methyl-imidazole-4-sulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-6-fluoro-3-[[3-(trifluoromethyl)phenyl]methyl]indan-5-yl]oxyethyl]-1-methyl-pyrazole-4-sulfonamide;

N-[[2-(azetidin-1-ylmethyl)-6-fluoro-3-[[3-(trifluoromethyl)phenyl]methyl]indan-5-yl]methyl]-1-cyclopropyl-methanesulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-6-fluoro-3-[[3-(trifluoromethyl)phenyl]methyl]indan-5-yl]ethyl]-1-cyclopropyl-methanesulfonamide;

N-[[2-(azetidin-1-ylmethyl)-6-fluoro-3-[[3-(trifluoromethyl)phenyl]methyl]indan-5-yl]methyl]cyclobutanesulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-6-fluoro-3-[[3-(trifluoromethyl)phenyl]methyl]indan-5-yl]ethyl]cyclobutanesulfonamide;

N-[[2-(azetidin-1-ylmethyl)-6-fluoro-3-[[3-(trifluoromethyl)phenyl]methyl]indan-5-yl]methyl]-1-methyl-imidazole-4-sulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-6-fluoro-3-[[3-(trifluoromethyl)phenyl]methyl]indan-5-yl]ethyl]-1-methyl-imidazole-4-sulfonamide;

N-[[2-(azetidin-1-ylmethyl)-6-fluoro-3-[[3-(trifluoromethyl)phenyl]methyl]indan-5-yl]methyl]-1-methyl-pyrazole-4-sulfonamide;

N-[2-[2-(azetidin-1-ylmethyl)-6-fluoro-3-[[3-(trifluoromethyl)phenyl]methyl]indan-5-yl]ethyl]-1-methyl-pyrazole-4-sulfonamide;

3-Methyl-3H-imidazole-4-sulfonic acid [2-(7-aminomethyl-8-benzyl-5,6,7,8-tetrahydro-naphthalen-2-yloxy)-ethyl]-amide;

Ethanesulfonic acid [2-(7-aminomethyl-8-benzyl-5,6,7,8-tetrahydro-naphthalen-2-yloxy)-ethyl]-amide;

N-[2-(7-Aminomethyl-8-benzyl-5,6,7,8-tetrahydro-naphthalen-2-yloxy)-ethyl]-C-cyclopropyl-methanesulfonamide;

3-Methyl-3H-imidazole-4-sulfonic acid [2-(8-benzyl-7-methylaminomethyl-5,6,7,8-tetrahydro-naphthalen-2-yloxy)-ethyl]-amide;

Ethanesulfonic acid [2-(8-benzyl-7-methylaminomethyl-5,6,7,8-tetrahydro-naphthalen-2-yloxy)-ethyl]-amide;

N-[2-(8-Benzyl-7-methylaminomethyl-5,6,7,8-tetrahydro-naphthalen-2-yloxy)-ethyl]-C-cyclopropyl-methanesulfonamide;

Ethanesulfonic acid [2-(7-azetidin-1-ylmethyl-8-benzyl-5,6,7,8-tetrahydro-naphthalen-2-yloxy)-ethyl]-amide;

N-[2-(7-Azetidin-1-ylmethyl-8-benzyl-5,6,7,8-tetrahydro-naphthalen-2-yloxy)-ethyl]-C-cyclopropyl-methanesulfonamide;

1-Methyl-1H-imidazole-4-sulfonic acid [2-(7-azetidin-1-ylmethyl-8-benzyl-5,6,7,8-tetrahydro-naphthalen-2-yloxy)-ethyl]-amide; and

1-Methyl-1H-imidazole-4-sulfonic acid (7-azetidin-1-ylmethyl-8-benzyl-5,6,7,8-tetrahydro-naphthalen-2-ylmethyl)-amide;

or a physiologically tolerated salt thereof.

19. A pharmaceutical composition which comprises a carrier and a compound of claim 1 .

20. A method for treating a neurologic or psychiatric disorder or pain in a mammalian patient in need thereof which comprises administering to the patient a therapeutically effective amount of a compound of claim 1 , wherein the neurologic disorder is selected from the group consisting of dementia, cognitive impairment, and attention deficit disorder, and wherein the psychiatric disorder is selected from the group consisting of anxiety disorder, depression, bipolar disorder, schizophrenia, and psychosis.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 26, 2014
From: ABBOTT LABORATORIES
To: ABBVIE INC.
Reel/Frame 034268/0986 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 9, 2013
From: ABBOTT GMBH & CO KG
To: ABBVIE DEUTSCHLAND GMBH & CO KG
Reel/Frame 030763/0308 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 22, 2012
From: HUTCHINS, CHARLES W.
To: ABBOTT LABORATORIES
Reel/Frame 028830/0486 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 8, 2012
From: LANGE, UDO; AMBERG, WILHELM; OCHSE, MICHAEL; BEHL, BERTHOLD; POHLKI, FRAUKE
To: ABBOTT GMBH & CO. KG
Reel/Frame 028746/0693 →