IP Library Granted Patent US 8,853,196
Granted Patent B2
US 8,853,196 · App. 13/566,051 · Granted Oct 7, 2014

Aminochromane, aminothiochromane and amino-1,2,3,4-tetrahydroquinoline derivatives, pharmaceutical compositions containing them, and their use in therapy

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Quick Facts
Patent No.
US 8,853,196
App. No.
13/566,051
Granted
Oct 7, 2014
Kind
B2
Abstract

The present invention relates to aminochromane, aminothiochromane and amino-1,2,3,4-tetrahydroquinoline derivatives of the formula (I) or a physiologically tolerated salt thereof. The invention relates to pharmaceutical compositions comprising such aminochromane, aminothiochromane and amino-1,2,3,4-tetrahydroquinoline derivatives, and the use of such aminochromane, aminothiochromane and amino-1,2,3,4-tetrahydroquinoline derivatives for therapeutic purposes. The aminochromane, aminothiochromane and amino-1,2,3,4-tetrahydroquinoline derivatives are GlyT1 inhibitors.

Claims (147)

1. Compounds of the formula (IV)

or a physiologically tolerated salt thereof,

wherein

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 2a , R 2b

are independently 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 together with the benzene ring atoms to which they are bound form a 5- or 6 membered ring;

R 3a , R 3b

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

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 17 ;

R 5 is optionally substituted C 6 -C 12 -aryl;

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 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; or

R 9 , R 1

together are 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 17 is hydrogen or C 1 -C 6 -alkyl.

2. The compound as claimed in claim 1 , wherein —Y-A 2 -X 1 — consists of 2, 3 or 4 atoms in its longest linear chain.

3. The compound as claimed in 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.

4. The compound as claimed in claim 1 , wherein A 1 is a bond, W is a bond and Y is —NR 9 —.

5. The compound as claimed in 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.

6. The compound as claimed in 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 —.

7. The compound as claimed in claim 1 , wherein R 2a , R 2b are hydrogen or halogen.

8. The compound as claimed in of claim 1 , wherein R 3a , R 3b are hydrogen or C 1 -C 6 -alkyl.

9. The compound as claimed in claim 1 , wherein R 4a is hydrogen, C 1 -C 6 -alkyl, C 3 -C 12 -cycloalkyl, C 3 -C 12 -cycloalkyl-C 1 -C 4 -alkyl, or C 3 -C 12 heterocyclyl, and R 4b is hydrogen or C 1 -C 6 -alkyl, 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.

10. The compound as claimed in claim 1 ,

wherein R 5 is phenyl optionally substituted with hydrogen, halogen, or halogenated C 1 -C 6 -alkyl.

11. The compound as claimed in 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;

W is a bond;

A 1 is a bond;

Q is —S(O) 2 —;

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

X 1 is —O— or C 1 -C 4 -alkylene;

R 2a , R 2b

are independently hydrogen or halogen;

R 3a , R 3b

are independently hydrogen or C 1 -C 6 -alkyl;

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

R 4b is hydrogen; or

R 4a , R 4b

together are C 1 -C 6 -alkylene;

R 5 is optionally substituted phenyl;

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.

12. The compound of claim 1 , or a physiologically tolerated salt thereof, wherein the compound or a physiologically tolerated salt thereof is selected from the group consisting of:

cis-N-(2-{[-4-Benzyl-3-(methylamino)-3,4-dihydro-2H-chromen-6-yl]oxy}ethyl)-1-methyl-1H-pyrazole-4-sulfonamide;

trans-N-(2-{[-4-Benzyl-3-(methylamino)-3,4-dihydro-2H-chromen-6-yl]oxy}ethyl)-1-methyl-1H-pyrazole-4-sulfonamide;

cis-N-(2-{[-4-Benzyl-3-(methylamino)-3,4-dihydro-2H-chromen-6-yl]oxy}ethyl)-1-methyl-1H-imidazole-4-sulfonamide;

trans-N-(2-{[-4-Benzyl-3-(methylamino)-3,4-dihydro-2H-chromen-6-yl]oxy}ethyl)-1-methyl-1H-imidazole-4-sulfonamide;

cis-N-(2-{[-4-Benzyl-3-(methylamino)-3,4-dihydro-2H-chromen-6-yl]oxy}ethyl)propane-1-sulfonamide;

trans-N-(2-{[-4-Benzyl-3-(methylamino)-3,4-dihydro-2H-chromen-6-yl]oxy}ethyl)propane-1-sulfonamide;

cis-N-(2-{[-4-Benzyl-3-(methylamino)-3,4-dihydro-2H-chromen-6-yl]oxy}ethyl)-1-cyclopropylmethanesulfonamide;

trans-N-(2-{[-4-Benzyl-3-(methylamino)-3,4-dihydro-2H-chromen-6-yl]oxy}ethyl)-1-cyclopropylmethanesulfonamide;

cis-1-Methyl-1H-imidazole-4-sulfonic acid (4-benzyl-3-methylamino-chroman-6-ylmethyl)-amide;

trans-1-Methyl-1H-imidazole-4-sulfonic acid (4-benzyl-3-methylamino-chroman-6-ylmethyl)-amide;

cis-N-{[4-Benzyl-3-(methylamino)-3,4-dihydro-2H-chromen-6-yl]methyl}-1-methyl-1H-pyrazole-4-sulfonamide;

trans-N-{[-4-Benzyl-3-(methylamino)-3,4-dihydro-2H-chromen-6-yl]methyl}-1-methyl-1H-pyrazole-4-sulfonamide;

cis-N-{[4-Benzyl-3-(methylamino)-3,4-dihydro-2H-chromen-6-yl]methyl}propane-1-sulfonamide (a) and trans-N-{[4-benzyl-3-(methylamino)-3,4-dihydro-2H-chromen-6-yl]methyl}propane-1-sulfonamide;

cis-N-{[4-Benzyl-3-(methylamino)-3,4-dihydro-2H-chromen-6-yl]methyl}-1-cyclopropylmethanesulfonamide;

trans-N-{[4-Benzyl-3-(methylamino)-3,4-dihydro-2H-chromen-6-yl]methyl}-1-cyclopropylmethanesulfonamide;

cis-N-{[4-Benzyl-3-(methylamino)-3,4-dihydro-2H-chromen-6-yl]methyl}ethane sulfonamide;

trans-N-{[4-benzyl-3-(methylamino)-3,4-dihydro-2H-chromen-6-yl]methyl}ethane sulfonamide;

1-Methyl- H-imidazole-4-sulfonic acid [2-((3S,4S)-3-azetidin-1-yl-4-benzyl-chroman-6-yloxy)-ethyl]-amide;

N-[2-((3S,4S)-3-Azetidin-1-yl-4-benzyl-chroman-6-yloxy)-ethyl]-C-cyclopropyl-methanesulfonamide;

1-Methyl-1H-imidazole-4-sulfonic acid ((3S,4S)-3-amino-4-benzyl-chroman-6-ylmethyl)-amide;

1-Methyl-1H-imidazole-4-sulfonic acid ((3R,4S)-3-amino-4-benzyl-chroman-6-ylmethyl)-amide;

Propane-1-sulfonic acid [2-((3S,4S)-3-azetidin-1-yl-4-benzyl-chroman-6-yloxy)-ethyl]-amide;

1-Methyl- H-pyrazole-4-sulfonic acid ((3R,4R)-3-azetidin-1-yl-4-benzyl-chroman-6-ylmethyl)-amide;

1-Methyl-1H-pyrazole-4-sulfonic acid [2-((3S,4S)-3-azetidin-1-yl-4-benzyl-chroman-6-yloxy)-ethyl]-amide;

1-Methyl-1H-imidazole-4-sulfonic acid ((3R,4R)-3-azetidin-1-yl-4-benzyl-chroman-6-ylmethyl)-amide;

Ethanesulfonic acid [24(3S,4S)-3-azetidin-1-yl-4-benzyl-chroman-6-yloxy)-ethyl]-amide;

Ethanesulfonic acid (3-azetidin-1-yl-4-benzyl-chroman-6-ylmethyl)-amide;

Propane-1-sulfonic acid (3-azetidin-1-yl-4-benzyl-chroman-6-ylmethyl)-amide;

N-(3-Azetidin-1-yl-4-benzyl-chroman-6-ylmethyl)-C-cyclopropyl-methane-sulfonamide;

1-Methyl-1H-imidazole-4-sulfonic acid [(3S,4S)-4-benzyl-3-(cyclohexylmethyl-amino)-chroman-6-1 methyl]-amide;

Ethanesulfonic acid ((3R,4R)-3-amino-4-benzyl-chroman-6-ylmethyl)-amide;

Ethanesulfonic acid ((3S,4R)-3-amino-4-benzyl-chroman-6-ylmethyl)-amide;

Cyclobutanesulfonic acid ((3R,4R)-4-benzyl-3-methylamino-chroman-6-ylmethyl)-amide;

Cyclobutanesulfonic acid ((3S,4R)-4-benzyl-3-methylamino-chroman-6-ylmethyl)-amide;

cis-Ethanesulfonic acid (-4-benzyl-7-fluoro-3-methylamino-chroman-6-ylmethyl)-amide;

trans-Ethanesulfonic acid (-4-benzyl-7-fluoro-3-methylamino-chroman-6-ylmethyl)-amide;

cis-Ethanesulfonic acid [2-(-4-benzyl-7-fluoro-3-methylamino-chroman-6-yloxy)-ethyl]-amide;

trans-Ethanesulfonic acid [2-(-4-benzyl-7-fluoro-3-methylamino-chroman-6-yloxy)-ethyl]-amide;

cis-1-Methyl-1H-imidazole-4-sulfonic acid (-4-benzyl-7-fluoro-3-methylamino-chroman-6-ylmethyl)-amide;

trans-1-Methyl-1H-imidazole-4-sulfonic acid (-4-benzyl-7-fluoro-3-methylamino-chroman-6-ylmethyl)-amide;

cis-N-((-4-benzyl-3-((2-cyclopropylethyl)amino)chroman-6-yl)methyl)-methyl-1H-imidazole-4-sulfonamide;

cis-N-((-4-benzyl-3-((2-cyclopentylethyl)amino)chroman-6-yl)methyl)-1-methyl-1H-imidazole-4-sulfonamide;

cis-N-((-4-benzyl-3-(propylamino)chroman-6-yl)methyl)-1-methyl-1H-imidazole-4-sulfonamide;

cis-N-((-4-benzyl-3-(neopentylamino)chroman-6-yl)methyl)-1-methyl-1H-imidazole-4-sulfonamide;

cis-N-((-4-benzyl-3-(isobutylamino)chroman-6-yl)methyl)-1-methyl-1H-imidazole-4-sulfonamide;

cis-N-((-4-benzyl-3-((cyclopropylmethyl)amino)chroman-6-yl)methyl)-1-methyl-1H-imidazole-4-sulfonamide;

cis-N-((-4-benzyl-3-(isopentylamino)chroman-6-yl)methyl)-1-methyl-1H-imidazole-4-sulfonamide;

cis-N-((-4-benzyl-3-((cyclopentylmethyl)amino)chroman-6-yl)methyl)-1-methyl-1H-imidazole-4-sulfonamide;

cis-N-((-4-benzyl-3-((cyclobutylmethyl)amino)chroman-6-yl)methyl)-1-methyl-1H-imidazole-4-sulfonamide;

Thiophene-2-sulfonic acid (3-amino-4-benzyl-chroman-6-ylmethyl)-amide;

3-Methyl-piperidine-1-sulfonic acid (3-amino-4-benzyl-chroman-6-ylmethyl)-amide;

Morpholine-4-sulfonic acid (3-amino-4-benzyl-chroman-6-ylmethyl)-amide;

1,3-Dimethyl-1H-pyrazole-4-sulfonic acid (3-amino-4-benzyl-chroman-6-ylmethyl)-amide;

1-Methyl-1H-pyrazole-3-sulfonic acid (3-amino-4-benzyl-chroman-6-ylmethyl)-amide;

Butane-2-sulfonic acid (3-amino-4-benzyl-chroman-6-ylmethyl)-amide;

Propane-2-sulfonic acid (3-amino-4-benzyl-chroman-6-ylmethyl)-amide;

Thiophene-3-sulfonic acid (3-amino-4-benzyl-chroman-6-ylmethyl)-amide;

2,5-Dimethyl-furan-3-sulfonic acid (3-amino-4-benzyl-chroman-6-ylmethyl)-amide;

2-Methyl-propane-1-sulfonic acid (3-amino-4-benzyl-chroman-6-ylmethyl)-amide;

5-Methyl-furan-2-sulfonic acid (3-amino-4-benzyl-chroman-6-ylmethyl)-amide;

5-Methyl-thiophene-2-sulfonic acid (3-amino-4-benzyl-chroman-6-ylmethyl)-amide;

Furan-3-sulfonic acid (3-amino-4-benzyl-chroman-6-ylmethyl)-amide;

2,5-Dimethyl-2H-pyrazole-3-sulfonic acid (3-amino-4-benzyl-chroman-6-ylmethyl)-amide;

4-Methyl-thiophene-2-sulfonic acid (3-amino-4-benzyl-chroman-6-ylmethyl)-amide;

1-Ethyl-1H-pyrazole-4-sulfonic acid (3-amino-4-benzyl-chroman-6-ylmethyl)-amide;

2,3-Dimethyl-3H-imidazole-4-sulfonic acid (3-amino-4-benzyl-chroman-6-ylmethyl)-amide;

1,5-Dimethyl-1H-pyrazole-4-sulfonic acid (3-amino-4-benzyl-chroman-6-ylmethyl)-amide;

cis-N-(-4-Benzyl-3-methylamino-chroman-6-ylmethyl)-methanesulfonamide;

trans-N-(-4-Benzyl-3-methylamino-chroman-6-ylmethyl)-methanesulfonamide;

cis-1-Methyl-1H-imidazole-4-sulfonic acid (-4-benzyl-3-pyrrolidin-1-yl-chroman-6-ylmethyl)-amide;

cis-Ethanesulfonic acid (-4-benzyl-3-pyrrolidin-1-yl-chroman-6-ylmethyl)-amide;

cis-N-(-4-Benzyl-3-pyrrolidin-1-yl-chroman-6-ylmethyl)-methanesulfonamide;

cis-N-(-4-Benzyl-3-pyrrolidin-1-yl-chroman-6-ylmethyl)-C-cyclopropyl-methanesulfonamide;

cis-1-Methyl-1H-pyrazole-4-sulfonic acid (-4-benzyl-3-pyrrolidin-1-yl-chroman-6-ylmethyl)-amide;

cis-N-(-3-Amino-4-benzyl-chroman-6-ylmethyl)-C-cyclopropyl-methanesulfonamide;

trans-N-(-3-Amino-4-benzyl-chroman-6-ylmethyl)-C-cyclopropyl-methanesulfonamide;

cis-Cyclobutanesulfonic acid (-3-amino-4-benzyl-chroman-6-ylmethyl)-amide;

trans-Cyclobutanesulfonic acid (-3-amino-4-benzyl-chroman-6-ylmethyl)-amide;

cis-Propane-1-sulfonic acid (-3-amino-4-benzyl-chroman-6-ylmethyl)-amide;

trans-Propane-1-sulfonic acid (-3-amino-4-benzyl-chroman-6-ylmethyl)-amide;

trans-Ethanesulfonic acid [2-(-4-benzyl-2,2-dimethylamino-chroman-6-yloxy)-ethyl]-amide;

cis-Propane-1-sulfonic acid [2-(-4-benzyl-2,2-dimethyl-3-methylamino-chroman-6-yloxy)-ethyl]-amide;

trans-Propane-1-sulfonic acid [2-(-4-benzyl-2,2-dimethyl-3-methylamino-chroman-6-yloxy)-ethyl]-amide;

cis-N-[2-(-4-Benzyl-2,2-dimethyl-3-methylamino-chroman-6-yloxy)-ethyl]-C-cyclopropyl-methanesulfonamide;

trans-N-[2-(-4-Benzyl-2,2-dimethyl-3-methylamino-chroman-6-yloxy)-ethyl]-C-cyclopropyl-methanesulfonamide; and

cis-Ethanesulfonic acid [2-(-4-benzyl-2,2-dimethyl-3-methylamino-chroman-6-yloxy)-ethyl]-amide.

13. Pharmaceutical composition which comprises a carrier and a compound of claim 1 .

14. 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 the compound of claim 1 .

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 16, 2013
From: ABBOTT GMBH & CO KG
To: ABBVIE DEUTSCHLAND GMBH & CO KG
Reel/Frame 030804/0429 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 19, 2012
From: AMBERG, WILHELM; LANGE, UDO; POHLKI, FRAUKE
To: ABBOTT GMBH & CO. KG
Reel/Frame 029156/0061 →