Aryl-substituted piperazine derivatives
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Abstract
Aryl-substituted piperazine derivatives are provided. Such compounds may be used to modulate MCH receptor activity in vivo or in vitro, and are particularly useful in the treatment of a variety of metabolic, feeding and sexual disorders in humans, domesticated companion animals and livestock animals. Pharmaceutical compositions and methods for treating such disorders are provided, as are methods for using such ligands for detecting MCH receptors (e.g., receptor localization studies).
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Citations
135 Claims
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1. (canceled)
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2. A compound of the formula:
- View Dependent Claims (15, 16)
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15. A compound or salt of claim 2, wherein the compound has the formula:
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16. A compound or salt of claim 2, wherein the compound has the formula:
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15. A compound or salt of claim 2, wherein the compound has the formula:
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3. A compound of the formula:
- View Dependent Claims (6, 7, 8, 14, 20, 21, 22, 23, 26, 29, 30, 34, 41, 45, 49, 50, 52, 55, 56, 68, 84, 86, 91, 92, 93, 94, 98, 99, 104, 116, 117, 118, 119, 120, 121, 122, 123, 124, 125, 131, 135)
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6. A compound or salt of claim 3, wherein V is absent.
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7. A compound or salt of claim 3, wherein V is —
- (C═
O)—
.
- (C═
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8. A compound or salt of claim 3, wherein n is 1.
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14. A compound or salt of claim 3, wherein the compound has the formula:
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20. A compound or salt of claim 3, wherein Y1, Y4 and Y5 are CH, Y3 is CR1, and Z is CR2.
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21. A compound or salt of claim 3, wherein Y1 is nitrogen, Y3, Y4 and Y5 are CR1, and Z is CR2.
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22. A compound or salt of claim 3, wherein Y1 and Y4 are nitrogen, Y3 and Y5 are CR1, and Z is CR2.
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23. A compound or salt of claim 3, wherein Y4 is nitrogen, Y1, Y3, and Ys are CR1, and Z is CR2.
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26. A compound or salt of claim 3, wherein each R1 is independently hydrogen, halogen, C1-C2alkyl, C1-C2alkoxy, or trifluoromethyl.
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29. A compound or salt of claim 3, wherein R2 is halogen, C1-C4alkyl, C1-C4alkoxy, or trifluoromethyl.
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30. A compound or salt of claim 29, wherein each R1 is hydrogen and R2 is trifluoromethyl.
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34. A compound or salt of claim 3 wherein R3 is methyl and R4 is hydrogen.
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41. A compound or salt of claim 3, wherein P is CR7, Q is CR8, U is CR9, and T is CR10.
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45. A compound or salt of claim 3, wherein R7, R8, R9, and R10 are each independently hydrogen, halogen, C1-C2alkyl, C1-C2alkoxy, haloC1-C2alkyl, or haloC1-C2alkoxy.
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49. A compound or salt of claim 45, wherein R7 and R8 are both methyl, and R9 and R10 are both hydrogen.
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50. A compound or salt of claim 3, wherein R11 is a group of the formula G-L-.
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52. A compound or salt of claim 50, wherein G is C1-C6alkyl, C2-C6alkenyl, or C2-C6alkynyl, each of which is substituted with from 0 to 3 substituents independently chosen from halogen and amino, and wherein G is substituted with from 1 to 5 substituents independently chosen from Ra and Rb.
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55. A compound or salt of claim 50, wherein:
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G is substituted with at least one substituent chosen from Ra and Rb; and
Rb is C1-C6alkoxy, (C1-C6alkoxy)C1-C6alkoxy, mono- or di-(C1-C8alkyl)aminoC0-C6alkyl, C2-C6alkanoyl, C1-C6alkylsulfonyl, C1-C6alkylthio, C1-C6alkylaminosulfonyl, C1-C6alkysulfonylamino, C1-C6alkoxycarbonyl, C2-C6alkanoylamino, mono- or di-(C1-C6alkyl)aminocarbonyl, or C1-C6alkyloxime, each of which is substituted with from 0 to 5 substituents independently chosen from halogen, amino, cyano, hydroxy, oxo, oxime, C1-C4alkyl, (C1-C4alkoxy)C0-C4alkyl, mono- and di-(C1-C4alkyl)amino, C2-C4alkanoyl, C3-C7cycloalkyl, C1-C4alkoxycarbonyl, haloC1-C2alkyl and haloC1-C2alkoxy.
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56. A compound or salt of claim 55, wherein:
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G is C1-C6alkyl, substituted with from 0 to 3 substituents independently chosen from halogen and amino;
wherein G is substituted with from 1 to 5 substituents independently chosen from;
(a) oxo, oxime, hydroxy, cyano, —
(C═
O)NH2, —
NH(C═
O)H, or imino; and
(b) C1-C6alkoxy, mono- or di-(C1-C8alkyl)amino, C1-C6alkoxycarbonyl, or C2-C6alkanoylamino, each of which is substituted with from 0 to 5 substituents independently chosen from halogen, oxo, C1-C4alkoxy, mono- and di-C1-C4alkylamino, C2-C4alkanoyl, C3-C7cycloalkyl, haloC1-C2alkyl, and haloC1-C2alkoxy.
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68. A compound or salt of claim 50, wherein R11 is a group of the formula G-L-, where L is O.
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84. A compound or salt of claim 3, wherein:
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R11 is a group of the formula G2-O—
; and
G2 is C1-C6alkyl that is substituted with from 0 to 3 substituents independently chosen from halogen and amino, wherein G2 is further substituted with from 1 to 5 substituents independently chosen from Ra, Rb and Rc, such that Rb is not N-methyl,N-cyclopentylamino, and Rc is not (heterocycle)C0-C6alkyl.
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86. A compound or salt of claim 84, wherein G2 is substituted with from 0 to 3 substituents independently chosen from halogen and amino, and wherein G2 is substituted with from 1 to 5 substituents independently chosen from Ra and Rb wherein:
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Ra is oxo, hydroxy, cyano, —
(C═
O)NH2, —
NH(C═
O)H, or imino; and
Rb is C1-C6alkoxy, mono- and di-(C1-C8alkyl)amino, C1-C6alkoxycarbonyl, or C2-C6alkanoylamino, each of which is substituted with from 0 to 5 substituents independently chosen from halogen, oxo, C1-C4alkoxy, mono- and di-C1-C4alkylamino, C2-C4alkanoyl, C3-C7cycloalkyl, haloC1-C2alkyl and haloC1-C2alkoxy.
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91. A compound of claim 3, wherein the compound satisfies the formula:
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92. A compound or salt of claim 91, wherein the compound satisfies the formula:
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93. A compound or salt of claim 92, wherein the compound satisfies the formula:
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94. A compound or salt of claim 92, wherein:
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R7 and R8 are independently hydrogen, halogen, C1-C2alkyl or haloC1-C2alkyl; and
R11 is a group of the formula G-L-, wherein G is C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, haloC1-C6alkyl, saturated C3-C10cycloalkyl or saturated 3- to 10-membered heterocycloalkyl;
each of which is substituted with from 0 to 3 substituents independently chosen from halogen, amino and C1-C6alkyl, wherein G is substituted with from 1 to 5 substituents independently chosen from Ra and Rb.
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98. A compound or salt of claim 3, wherein the compound satisfies the formula:
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99. A compound or salt of claim 98, wherein the compound satisfies the formula:
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104. A pharmaceutical composition, comprising a compound or salt of claim 3, in combination with at least one physiologically acceptable carrier or excipient.
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116. A method for treating a disease or disorder associated with MCH receptor activation, comprising administering to a patient in need of such treatment a therapeutically effective amount of a compound of claim 3.
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117. The method of claim 116, wherein the disease or disorder is an eating disorder, sexual disorder, diabetes, heart disease or stroke.
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118. The method of claim 117, wherein the compound or salt is administered orally.
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119. The method of claim 117, wherein the compound or salt is administered intranasally, intravenously or topically.
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120. The method of claim 117, wherein the patient is a human.
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121. The method of claim 117, wherein the patient is a dog or a cat.
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122. A method for treating obesity, comprising administering to a patient in need of such treatment a therapeutically effective amount of a compound of claim 3.
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123. The method of claim 122, wherein the compound or salt is administered orally.
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124. The method of claim 122, wherein the patient is a human.
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125. The method of claim 122, wherein the patient is a dog or a cat.
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131. A packaged pharmaceutical preparation, comprising:
- (i) a pharmaceutical composition of claim 104 in a container; and
(ii) instructions for using the composition to treat a patient suffering from a disorder associated with MCH receptor activation.
- (i) a pharmaceutical composition of claim 104 in a container; and
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135. A compound or salt according to claim 3, wherein the compound is:
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{(6R,9aS)-6-[4-(2-methoxy-ethoxy)-2,3-dimethylphenyl]-octahydro-pyrido[1,2-a]pyrazin-2-yl}-(6-trifluoromethyl-pyridin-3-yl)-methanone;
{(6R,9aS)-6-[4-(2-hydroxy-ethoxy)-2,3-dimethyl-phenyl]-octa-hydro-pyrido[1,2-a]pyrazin-2-yl}-(6-trifluoromethyl-pyridin-3-yl)-methanone;
{(6R,9aS)-6-[4-((S)-2-Hydroxy-propoxy)-2,3-dimethyl-phenyl]-octahydro-pyrido[1,2-a]pyrazin-2-yl}-(6-trifluoromethyl-pyridin-3-yl)-methanone;
{(6R,9aS)-6-[4-((R)-2-Hydroxy-propoxy)-2,3-dimethyl-phenyl]-octahydro-pyrido[1,2-a]pyrazin-2-yl}-(6-trifluoromethyl-pyridin-3-yl)-methanone;
1-{2,3-Dimethyl-4-[(6R,9aS)-2-(6-trifluoromethyl-pyridine-3-carbonyl)-octahydro-pyrido[1,2-a]pyrazin-6-yl]-phenoxy}-propan-2-one;
1-{2,3-Dimethyl-4-[(6R,9aS)-2-(6-trifluoromethyl-pyridine-3-carbonyl)-octahydro-pyrido[1,2-a]pyrazin-6-yl]-phenoxy}-propan-2-one oxime;
(6-Chloropyridin-3-yl)-((1S,4S)-5-{(S)-1-[4-(2-methoxy-ethoxy)-2,3-dimethylphenyl]-ethyl}-2,5-diazabicyclo[2.2.1]hept-2-yl)-methanone;
(6-Ethylpyridin-3-yl)-((1S,4S)-5-{(S)-1-[4-(2-methoxy-ethoxy)-2,3-dimethylphenyl]-ethyl}-2,5-diazabicyclo[2.2.1]hept-2-yl)-methanone;
[(6R,8aS)-6-(4-methoxy-2,3-dimethylphenyl)-hexahydro-pyrrolo[1,2-a]pyrazin-2-yl]-(6-trifluoromethyl-pyridin-3-yl)-methanone;
N-(3-{4-[(6R,9aS)-2-(4-chloro-3-methoxy-phenyl)-octahydro-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}-propyl)-acetamide;
N-(3-{4-[(6R,9aS)-2-(4-fluoro-3-methoxy-phenyl)-octahydro-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}-propyl)-acetamide;
4-(4-Chloro-3-trifluoromethyl-phenyl)-1-[4-(2-methoxy-ethoxy)-2,3-dimethyl-benzyl]-piperidin-4-ol;
2-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]-N,N-dimethylethanamine;
1-{1-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]ethyl}-4-[4-(trifluoromethyl)benzoyl]piperazine;
2-[2,3-dimethyl-4-((1R)-1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]-N,N-dimethylethanamine;
3-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]-N,N-dimethylpropan-1-amine;
1-(4-chlorobenzoyl)-4-{1-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]ethyl}piperazine;
1-(4-chlorobenzoyl)-4-{1-[4-(2-ethoxyethoxy)-2,3-dimethylphenyl]ethyl}piperazine;
ethyl (4-{1-[4-(4-chlorobenzoyl)piperazin-1-yl]ethyl}-2,3-dimethylphenoxy)acetate;
1-(4-{1-[4-(4-chlorobenzoyl)piperazin-1-yl]ethyl}-2,3-dimethylphenoxy)-2-methylpropan-2-ol;
1-(4-chlorobenzoyl)-4-{(1R)-1-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]ethyl}piperazine;
3-(4-{1-[4-(4-chlorobenzoyl)piperazin-1-yl]ethyl}-2,3-dimethylphenoxy)-N,N-dimethylpropan-1-amine;
2-(4-{1-[4-(4-chlorobenzoyl)piperazin-1-yl]ethyl}-2,3-dimethylphenoxy)ethanol;
2-(4-{1-[4-(4-chlorobenzoyl)piperazin-1-yl]ethyl}-2,3-dimethylphenoxy)-N-methylethanamine;
2-(4-{1-[4-(4-chlorobenzoyl)piperazin-1-yl]ethyl}-2,3-dimethylphenoxy)ethanamine;
(1S,4S)-2-{(1R)-1-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]ethyl}-5-[4-(trifluoromethyl)benzoyl]-2,5-diazabicyclo[2.2.1]heptane;
1-(4-chlorobenzoyl)-4-((1R)-1-{2,3-dimethyl-4-[2-(1-methylpyrrolidin-2-yl)ethoxy]phenyl}ethyl)piperazine;
2-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]-N,N-dimethylethanamine;
3-[2,3-dimethyl-4-((1S)-1-{4-[4-(trifluoromethyl)benzoyl]-piperazin-1-yl}ethyl)phenoxy]-N,N-dimethylpropan-1-amine;
3-[2,3-dimethyl-4-((1R)-1-{4-[4-(trifluoromethyl)benzoyl]-piperazin-1-yl}ethyl)phenoxy]-N,N-dimethylpropan-1-amine;
1-(4-chlorobenzoyl)-4-(1-{2,3-dimethyl-4-[3-(methylthio)-propoxy]phenyl}ethyl)piperazine;
1-(4-chlorobenzoyl)-4-(1-{2,3-dimethyl-4-[3-(methylsulfonyl)-propoxy]phenyl}ethyl)piperazine;
3-(4-{1-[4-(4-chlorobenzoyl)piperazin-1-yl]ethyl}-2,3-dimethylphenoxy)-N-methylpropan-1-amine;
3-[2,3-dimethyl-4-((1S)-1-{(1S,4S)-5-[4-(trifluoromethyl)benzoyl]-2,5-diazabicyclo[2.2.1]hept-2-yl}ethyl)phenoxy]-N,N-dimethylpropan-1-amine;
(1R,4R)-2-(4-chlorobenzoyl)-5-{(1R)-1-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]ethyl}-2,5-diazabicyclo[2.2.1]heptane;
3-[2,3-dimethyl-4-((S)-1-{(1S,4S)-5-[4-(trifluoromethyl)benzoyl]-2,5-diazabicyclo[2.2.1]hept-2-yl}ethyl)phenoxy]-N-methylpropan-1-amine;
3-[2,3-dimethyl-4-((1R)-1-{(1S,4S)-5-[4-(trifluoromethyl)benzoyl]-2,5-diazabicyclo[2.2.1]hept-2-yl}ethyl)phenoxy]-N,N-dimethylpropan-1-amine;
3-(4-{1-[4-(4-chloro-benzoyl)piperazin-1-yl]ethyl}-2,3-dimethylphenoxy)propan-1-ol;
(1R,4R)-2-{(1R)-1-[4-(3-methoxypropoxy)-2,3-dimethylphenyl]ethyl}-5-[4-(trifluoromethyl)benzoyl]-2,5-diazabicyclo[2.2.1]heptane;
(1R,4R)-2-{(1S)-1-[4-(3-methoxypropoxy)-2,3-dimethylphenyl]ethyl}-5-[4-(trifluoromethyl)benzoyl]-2,5-diazabicyclo[2.2.1]heptane;
(1R,4R)-2-(4-chlorobenzoyl)-5-{(1R)-1-[4-(3-methoxypropoxy)-2,3-dimethylphenyl]ethyl}-2,5-diazabicyclo[2.2.1]heptane;
1-(4-chlorobenzoyl)-4-{1-[4-(3-chloropropoxy)-2,3-dimethylphenyl]ethyl}piperazine 3-{4-[(6R,9aS)-2-(4-chlorobenzoyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}-N,N-dimethylpropan-1-amine;
(1S,4S)-2-{(1S)-1-[4-(difluoromethoxy)-2,3-dimethylphenyl]ethyl}-5-[4-(trifluoromethyl)benzoyl]-2,5-diazabicyclo[2.2.1]heptane;
3-(4-{(1S)-1-[(1S,4S)-5-(4-chlorobenzoyl)-2,5-diazabicyclo[2.2.1]hept-2-yl]ethyl}-2,3-dimethylphenoxy)-N-methylpropan-1-amine;
N-[3-(4-{(1S)-1-[(1S,4S)-5-(4-chlorobenzoyl)-2,5-diazabicyclo[2.2.1]hept-2-yl]ethyl}-2,3-dimethylphenoxy)propyl]-N-methylacetamide;
3-[2,3-dimethyl-4-((1R)-1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]propan-1-amine;
2-[2,3-dimethyl-4-((1R)-1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]-2,2-difluoroethanol;
3-(4-{(1R)-1-[4-(4-chlorobenzoyl)piperazin-1-yl]ethyl}-2,3-dimethylphenoxy)-N-isopropylpropan-1-amine;
3-[2,3-dimethyl-4-((1S)-1-{(1S,4S)-5-[4-(trifluoromethyl)benzoyl]-2,5-diazabicyclo[2.2.1]hept-2-yl}ethyl)phenoxy]propan-1-amine;
3-(4-{(1R)-1-[4-(4-chlorobenzoyl)piperazin-1-yl]ethyl}-2,3-dimethylphenoxy)-N,N-dimethylpropan-1-amine;
4-[2,3-dimethyl-4-((1R)-1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]butanenitrile;
4-[2,3-dimethyl-4-((1S)-1-{(1S,4S)-5-[4-(trifluoromethyl)benzoyl]-2,5-diazabicyclo[2.2.1]hept-2-yl}ethyl)phenoxy]butanenitrile;
4-(4-{(1R)-1-[4-(4-chlorobenzoyl)piperazin-1-yl]ethyl}-2,3-dimethylphenoxy)-2-methylbutan-2-ol;
N-[3-(4-{(1R)-1-[4-(4-chlorobenzoyl)piperazin-1-yl]ethyl}-2,3-dimethylphenoxy)-propyl]cyclopentanamine;
4-(4-{(1R)-1-[4-(4-chlorobenzoyl)piperazin-1-yl]ethyl}-2,3-dimethylphenoxy)-2-methylbutan-2-amine;
1-(1-{2,3-dimethyl-4-[2-(methylthio)ethoxy]phenyl}ethyl)-4-[4-(trifluoromethyl)-benzoyl]piperazine;
1-(4-chlorobenzoyl)-4-{(1R)-1-[4-(3-chloropropoxy)-2,3-dimethylphenyl]ethyl}piperazine;
3-[2,3-dimethyl-4-((1R)-1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]-N-methylpropan-1-amine;
3-(4-{(1R)-1-[4-(4-chlorobenzoyl)piperazin-1-yl]ethyl}-2,3-dimethylphenoxy)-N-methylpropan-1-amine;
4-(4-{(1R)-1-[4-(4-chlorobenzoyl)piperazin-1-yl]ethyl}-2,3-dimethyl-phenoxy)butanenitrile;
1-(1-{2,3-dimethyl-4-[2-(methylsulfonyl)ethoxy]phenyl}ethyl)-4-[4-(trifluoromethyl)-benzoyl]piperazine;
4-[2,3-dimethyl-4-((1R)-1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]-2-methylbutan-2-amine;
2-(4-{(1R)-1-[4-(4-chlorobenzoyl)piperazin-1-yl]ethyl}-2,3-dimethyl-phenoxy)acetamide;
3-(4-{(1R)-1-[4-(4-chlorobenzoyl)piperazin-1-yl]ethyl}-2,3-dimethylphenoxy)-propan-1-amine;
4-[2,3-dimethyl-4-((1R)-1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]butan-1-amine;
N-{3-[2,3-dimethyl-4-((1R)-1-{4-[4-(trifluoromethyl)benzoyl]-piperazin-1-yl}ethyl)phenoxy]-1,1-dimethylpropyl}acetamide;
N-[3-(4-{(1R)-1-[4-(4-chlorobenzoyl)piperazin-1-yl]ethyl}-2,3-dimethyl-phenoxy)propyl]acetamide;
N-[3-(4-{(1R)-1-[4-(4-chlorobenzoyl)piperazin-1-yl]ethyl}-2,3-dimethylphenoxy)-1,1-dimethylpropyl]acetamide;
1-[4-(2-methoxyethoxy)-2,3-dimethylbenzyl]-4-[4-(trifluoromethyl)benzoyl]piperazine;
4-[2,3-dimethyl-4-((1S)-1-{(1S,4S)-5-[4-(trifluoromethyl)benzoyl]-2,5-diazabicyclo[2.2.1]hept-2-yl}ethyl)phenoxy]-N-methylbutan-1-amine;
4-[2,3-dimethyl-4-((1S)-1-{(1S,4S)-5-[4-(trifluoromethyl)benzoyl]-2,5-diazabicyclo[2.2.1]hept-2-yl}ethyl)phenoxy]-N,N-dimethylbutan-1-amine;
4-[2,3-dimethyl-4-((1S)-1-{(1S,4S)-5-[4-(trifluoromethyl)benzoyl]-2,5-diazabicyclo[2.2.1]hept-2-yl}ethyl)phenoxy]butan-1-amine;
3-[2,3-dimethyl-4-({4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}methyl)phenoxy]propan-1-amine;
2-[2,3-dimethyl-4-((1R)-1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]ethanamine;
2-[2,3-dimethyl-4-((1R)-1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]-N-methylethanamine;
2-[2,3-dimethyl-4-((1S)-1-{(1S,4S)-5-[4-(trifluoromethyl)benzoyl]-2,5-diazabicyclo[2.2.1]hept-2-yl}ethyl)phenoxy]ethanamine;
2-[2,3-dimethyl-4-((1S)-1-{(1S,4S)-5-[4-(trifluoromethyl)benzoyl]-2,5-diazabicyclo[2.2.1]hept-2-yl}ethyl)phenoxy]-N-methylethanamine;
2-[2,3-dimethyl-4-((1S)-1-{(1S,4S)-5-[4-(trifluoromethyl)benzoyl]-2,5-diazabicyclo[2.2.1]hept-2-yl}ethyl)phenoxy]-N,N-dimethylethanamine;
2-(2,3-dimethyl-4-{2-[4-(trifluoromethyl)benzoyl]octahydro-2H-pyrido[1,2-a]pyrazin-6-yl}phenoxy)-N,N-dimethylethanamine;
4-(2,3-dimethyl-4-{2-[4-(trifluoromethyl)benzoyl]octahydro-2H-pyrido[1,2-a]pyrazin-6-yl}phenoxy)-N,N-dimethylbutan-1-amine;
(2,3-dimethyl-4-{2-[4-(trifluoromethyl)benzoyl]octahydro-2H-pyrido[1,2-a]pyrazin-6-yl}phenoxy)acetonitrile;
6-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]-2-[4-(trifluoromethyl)benzoyl]octahydro-2H-pyrido-1,2-a]pyrazine;
6-[4-(3-methoxypropoxy)-2,3-dimethylphenyl]-2-[4-(trifluoromethyl)benzoyl]octahydro-2H-pyrido[1,2-a]pyrazine;
5-(2,3-dimethyl-4-{(6R,9aS)-2-[4-(trifluoromethyl)benzoyl]octa-hydro-2H-pyrido[1,2-a]pyrazin-6-yl}phenoxy)pentanenitrile;
4-(2,3-dimethyl-4-{(6R,9aS)-2-[4-(trifluoromethyl)benzoyl]octahydro-2H-pyrido[1,2-a]pyrazin-6-yl}phenoxy)butanenitrile;
(2R)-1-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]-3-[(2-hydroxyethyl)amino]propan-2-ol;
(3S)-4-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]-3-hydroxybutanenitrile;
1-(2,3-dimethyl-4-{(6R,9aS)-2-[4-(trifluoromethyl)benzoyl]octa-hydro-2H-pyrido[1,2-a]pyrazin-6-yl}phenoxy)-2-methylpropan-2-ol;
2-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]-N,N-dimethylacetamide;
2-(2,3-dimethyl-4-{(6R,9aS)-2-[4-(trifluoromethyl)benzoyl]octahydro-2H-pyrido[1,2-a]pyrazin-6-yl}phenoxy)-N-ethyl-N-methylacetamide;
(6R,9aS)-6-[4-(allyloxy)-2,3-dimethylphenyl]-2-[4-(trifluoro-methyl)benzoyl]octahydro-2H-pyrido[1,2-a]pyrazine;
3-(2,3-dimethyl-4-{(6R,9aS)-2-[4-(trifluoromethyl)benzoyl]octa-hydro-2H-pyrido[1,2-a]pyrazin-6-yl}phenoxy)propan-1-ol;
(1S,4S)-2-[(6-chloropyridin-3-yl)carbonyl]-5-{(1S)-1-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]ethyl}-2,5-diazabicyclo[2.2.1]heptane;
(1S,4S)-2-{(1S)-1-[4-(2-methoxyethoxy)-2,3-dimethyl-phenyl]ethyl}-5-{[6-(trifluoro-methyl)pyridin-3-yl]carbonyl}-2,5-diazabicyclo[2.2. I]heptane;
(2S)-1-[(cyclopropylmethyl)-amino]-3-(2,3-dimethyl-4-{(6R,9aS)-2-[4-(trifluoromethyl)-benzoyl]octahydro-2H-pyrido[1,2-a]pyrazin-6-yl}phenoxy)propan-2-ol;
(2S)-1-(cyclopentylamino)-3-(2,3-dimethyl-4-{(6R,9aS)-2-[4-(trifluoromethyl)benzoyl]octahydro-2H-pyrido[1,2-a]pyrazin-6-yl}phenoxy)propan-2-ol;
(1S,4S)-2-[(5-ethylpyridin-2-yl)carbonyl]-5-{(1S)-1-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]ethyl}-2,5-diazabicyclo[2.2.1]heptane;
2-[2,3-dimethyl-4-((1R)-1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]-N-ethylacetamide;
2-[2,3-dimethyl-4-((1R)-1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]acetamide;
(1S,4S)-2-{(1S)-1-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]ethyl}-5-{[6-(methylthio)pyridin-3-yl]carbonyl}-2,5-diazabicyclo[2.2.1]heptane;
(1S,4S)-2-{(1S)-1-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]ethyl}-5-[(6-methylpyridin-3-yl)carbonyl]-2,5-diazabicyclo[2.2.1]heptane;
(6R,9aS)-6-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]-2-[4-(trifluoromethyl)benzoyl]octahydro-2H-pyrido[1,2-a]pyrazine;
2-[2,3-dimethyl-4-((1R)-1-{(1R,4R)-5-[4-(trifluoromethyl)benzoyl]-2,5-diazabicyclo[2.2.1]hept-2-yl}ethyl)phenoxy]-N-methylacetamide;
2-[2,3-dimethyl-4-((1R)-1-{(1R,4R)-5-[4-(trifluoromethyl)benzoyl]-2,5-diazabicyclo[2.2.1]hept-2-yl}ethyl)phenoxy]-N,N-dimethylacetamide;
(2S)-1-[2,3-dimethyl-4-((1R)-1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]-3-[(2-methoxyethyl)amino]propan-2-ol;
(2R)-1-amino-3-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]-piperazin-1-yl}ethyl)-phenoxy]propan-2-ol;
(3R)-4-(2,3-dimethyl-4-{(6R,9aS)-2-[4-(trifluoromethyl)benzoyl]octa-hydro-2H-pyrido[1,2-a]pyrazin-6-yl}phenoxy)-3-hydroxybutanenitrile;
(3S)-4-(2,3-dimethyl-4-{(6R,9aS)-2-[4-(trifluoromethyl)benzoyl]octa-hydro-2H-pyrido[1,2-a]pyrazin-6-yl}phenoxy)-3-hydroxybutanenitrile;
(2R)-1-(dimethylamino)-3-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]propan-2-ol;
(1S,4S)-2-[(6-ethylpyridin-3-yl)carbonyl]-5-{(1S)-1-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]ethyl}-2,5-diazabicyclo[2.2.1]heptane;
(1S,4S)-2-[(6-isobutylpyridin-3-yl)carbonyl]-5-{(1S)-1-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]ethyl}-2,5-diazabicyclo[2.2.1]heptane;
2-[2,3-dimethyl-4-((1R)-1-{(1R,4R)-5-[4-(trifluoromethyl)benzoyl]-2,5-diazabicyclo[2.2.1]hept-2-yl}ethyl)phenoxy]acetamide;
{2,3-dimethyl-4-[(1S)-1-((1S,4S)-5-{[6-(trifluoromethyl)pyridin-3-yl]carbonyl}-2,5-diazabicyclo[2.2.1]hept-2-yl)ethyl]phenoxy}acetonitrile;
2-{2,3-dimethyl-4-[(1S)-1-((1S,4S)-5-{[6-(trifluoromethyl)pyridin-3-yl]carbonyl}-2,5-diazabicyclo[2.2.1]hept-2-yl)ethyl]phenoxy}acetamide;
(3S)-4-[2,3-dimethyl-4-((1S)-1-{(1S,4S)-5-[4-(trifluoromethyl)-benzoyl]-2,5-diazabicyclo-[2.2.1]hept-2-yl}ethyl)phenoxy]-3-hydroxybutanenitrile;
(2S)-1-amino-3-[2,3-dimethyl-4-((S)-1-{(1S,4S)-5-[4-(trifluoromethyl)benzoyl]-2,5-diazabicyclo[2.2.1]hept-2-yl}ethyl)phenoxy]propan-2-ol;
(2S)-1-[2,3-dimethyl-4-((1S)-1-{(1S,4S)-5-[4-(trifluoromethyl)-benzoyl]-2,5-diazabicyclo-[2.2.1]hept-2-yl}ethyl)phenoxy]-3-[(2-methoxyethyl)amino]propan-2-ol;
(3R)-4-[2,3-dimethyl-4-((1S)-1-{(1S,4S)-5-[4-(trifluoromethyl)-benzoyl]-2,5-diazabicyclo[2.2.1]-hept-2-yl}ethyl)phenoxy]-3-hydroxybutanenitrile;
(2R)-1-amino-3-[2,3-dimethyl-4-((1S)-1-{(1S,4S)-5-[4-(trifluoromethyl)benzoyl]-2,5-diazabicyclo[2.2.1]hept-2-yl}ethyl)phenoxy]propan-2-ol;
(2R)-1-[2,3-dimethyl-4-((1S)-1-{(1S,4S)-5-[4-(trifluoromethyl)-benzoyl]-2,5-diazabicyclo[2.2.1]-hept-2-yl}ethyl)phenoxy]-3-[(2-methoxyethyl)amino]propan-2-ol;
4-{2,3-dimethyl-4-[(1S)-1-((1S,4S)-5-{[6-(trifluoromethyl)pyridin-3-yl]carbonyl}-2,5-diazabicyclo-[2.2.1]hept-2-yl)ethyl]phenoxy}-butanenitrile;
2-(2,3-dimethyl-4-{(6R,9aS)-2-[4-(trifluoromethyl)benzoyl]octahydro-2H-pyrido[1,2-a]pyrazin-6-yl}phenoxy)acetamide;
2-(2,3-dimethyl-4-{(6R,9aS)-2-[4-(trifluoromethyl)benzoyl]octahydro-2H-pyrido[1,2-a]pyrazin-6-yl}phenoxy)-N-methylacetamide;
2-(2,3-dimethyl-4-{(6R,9aS)-2-[4-(trifluoromethyl)benzoyl]octahydro-2H-pyrido[1,2-a]pyrazin-6-yl}phenoxy)-N,N-dimethylacetamide;
2-{2,3-dimethyl-4-[(1S)-1-((1S,4S)-5-{[6-(trifluoromethyl)pyridin-3-yl]carbonyl}-2,5-diazabicyclo-[2.2.1]hept-2-yl)ethyl]phenoxy}-N-methylacetamide;
2-{2,3-dimethyl-4-[(1S)-1-((1S,4S)-5-{[6-(trifluoromethyl)pyridin-3-yl]carbonyl}-2,5-diazabicyclo-[2.2.1]hept-2-yl)ethyl]phenoxy}-N,N-dimethylacetamide;
N-(3-{2,3-dimethyl-4-[(1S)-1-((1S,4S)-5-{[6-(trifluoromethyl)-pyridin-3-yl]carbonyl}-2,5-diazabicyclo[2.2.1]hept-2-yl)ethyl]phenoxy}propyl)acetamide;
(6R,9aS)-6-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]-2-{[6-(trifluoromethyl)pyridin-3-yl]carbonyl}octahydro-2H-pyrido[1,2-a]pyrazine;
(6R,9aS)-6-[4-(3-methoxypropoxy)-2,3-dimethylphenyl]-2-{[6-(trifluoromethyl)pyridin-3-yl]carbonyl}octahydro-2H-pyrido[1,2-a]pyrazine;
[2,3-dimethyl-4-((6R,9aS)-2-{[6-(trifluoromethyl)pyridin-3-yl]carbonyl}octahydro-2H-pyrido[1,2-a]pyrazin-6-yl)phenoxy]acetonitrile;
1-{2,3-dimethyl-4-[(1S)-1-((1S,4S)-5-{[6-(trifluoromethyl)pyridin-3-yl]carbonyl}-2,5-diazabicyclo-[2.2.1]hept-2-yl)ethyl]phenoxy}-2-methylpropan-2-ol;
2-{2,3-dimethyl-4-[(1S)-1-((1S,4S)-5-{[6-(trifluoromethyl)pyridin-3-yl]carbonyl}-2,5-diazabicyclo[2.2.1]hept-2-yl)ethyl]phenoxy}ethanamine;
N-(2-{2,3-dimethyl-4-[(1S)-1-((1S,4S)-5-{[6-(trifluoromethyl)-pyridin-3-yl]carbonyl}-2,5-diazabicyclo[2.2.1]hept-2-yl)ethyl]-phenoxy}ethyl)acetamide;
(2R)-1-amino-3-(2,3-dimethyl-4-{(6R,9aS)-2-[4-(trifluoromethyl)-benzoyl]octahydro-2H-pyrido[1,2-a]pyrazin-6-yl}phenoxy)propan-2-ol;
(2S)-3-{2,3-dimethyl-4-[(1S)-1-((1S,4S)-5-{[6-(trifluoromethyl)-pyridin-3-yl]carbonyl}-2,5-diazabicyclo[2.2.1]hept-2-yl)ethyl]-phenoxy}-2-methylpropan-1-ol;
(2R)-3-{2,3-dimethyl-4-[(1S)-1-((1S,4S)-5-{[6-(trifluoromethyl)-pyridin-3-yl]carbonyl}-2,5-diazabicyclo[2.2.1]hept-2-yl)ethyl]-phenoxy}-2-methylpropan-1-ol;
(1S,4S)-2-{(1S)-1-[4-(2-methoxyethoxy)-2,3-dimethyl-phenyl]ethyl}-5-{[5-(trifluoro-methyl)pyridin-2-yl]carbonyl}-2,5-diazabicyclo[2.2.1]heptane;
(1S,4S)-2-[4-(2-methoxyethoxy)-2,3-dimethylbenzyl]-5-[4-(trifluoromethyl)benzoyl]-2,5-diazabicyclo[2.2.1]heptane;
2-[2,3-dimethyl-4-((6R,9aS)-2-{[6-(trifluoromethyl)pyridin-3-yl]-carbonyl}octahydro-2H-pyrido[1,2-a]pyrazin-6-yl)phenoxy]ethanol;
(6R,9aS)-6-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]-2-{[5-(trifluoromethyl)pyridin-2-yl]carbonyl}octahydro-2H-pyrido[1,2-a]pyrazine;
(1S,4S)-2-[(2-ethyl-1,3-thiazol-4-yl)carbonyl]-5-{(1S)-1-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]ethyl}-2,5-diazabicyclo[2.2.1]heptane;
(6R,9aS)-6-[4-(2-ethoxyethoxy)-2,3-dimethylphenyl]-2-{[6-(trifluoro-methyl)pyridin-3-yl]carbonyl}-octahydro-2H-pyrido[1,2-a]pyrazine;
5-[((1S,4S)-5-{(1S)-1-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]ethyl}-2,5-diazabicyclo[2.2.1]hept-2-yl)carbonyl]-2,1,3-benzoxadiazole;
5-[((1S,4S)-5-{(1S)-1-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]ethyl}-2,5-diazabicyclo[2.2.1]hept-2-yl)carbonyl]-2,1,3-benzothiadiazole;
(6R,9aS)-6-{4-[2-(2-methoxy-ethoxy)ethoxy]-2,3-dimethyl-phenyl}-2-{[6-(trifluoromethyl)-pyridin-3-yl]carbonyl}octahydro-2H-pyrido[1,2-a]pyrazine;
(1S,4S)-2-{(1S)-1-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]ethyl}-5-[(5-methyl-2-thienyl)carbonyl]-2,5-diazabicyclo[2.2. I]heptane;
(1S,4S)-2-{(1S)-1-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]ethyl}-5-(3-thienylcarbonyl)-2,5-diazabicyclo[2.2.1]heptane;
(1S,4S)-2-{(1S)-1-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]ethyl}-5-[4-(1H-pyrazol-1-yl)benzoyl]-2,5-diazabicyclo[2.2.1]heptane;
(1S,4S)-2-{(1S)-1-[4-(2-methoxy-ethoxy)-2,3-dimethylphenyl]ethyl}-5-{[2-(trifluoromethyl)-1,3-thiazol-4-yl]carbonyl}-2,5-diazabicyclo[2.2.1]heptane;
(1S,4S)-2-[(2-chloro-1,3-thiazol-4-yl)carbonyl]-5-{(1S)-1-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]ethyl}-2,5-diazabicyclo[2.2.1]heptane;
(1S,4S)-2-[(2-chloro-5-methyl-1,3-thiazol-4-yl)carbonyl]-5-{(1S)-1-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]ethyl}-2,5-diazabicyclo[2.2.1]heptane;
3-[2,3-dimethyl-4-((6R,9aS)-2-{[6-(trifluoromethyl)pyridin-3-yl]-carbonyl}octahydro-2H-pyrido[1,2-a]pyrazin-6-yl)phenoxy]propan-1-ol;
1-[2,3-dimethyl-4-((6R,9aS)-2-{[6-(trifluoromethyl)pyridin-3-yl]-carbonyl}octahydro-2H-pyrido[1,2-a]pyrazin-6-yl)phenoxy]acetone;
N-[(2R)-3-(2,3-dimethyl-4-{(6R,9aS)-2-[4-(trifluoromethyl)-benzoyl]octahydro-2H-pyrido-[1,2-a]pyrazin-6-yl}phenoxy)-2-hydroxypropyl]acetamide;
3-[2,3-dimethyl-4-((6R,9aS)-2-{[6-(trifluoromethyl)pyridin-3-yl]carbonyl}octahydro-2H-pyrido[1,2-a]pyrazin-6-yl)phenoxy]propan-1-amine;
(2E)-1-[2,3-dimethyl-4-((6R,9aS)-2-{[6-(trifluoromethyl)pyridin-3-yl]carbonyl}octahydro-2H-pyrido[1,2-a]pyrazin-6-yl)phenoxy]acetone oxime;
N-{(2R)-3-[2,3-dimethyl-4-((1S)-1-{(1S,4S)-5-[4-(trifluoromethyl)-benzoyl]-2,5-diazabicyclo[2.2.1]-hept-2-yl}ethyl)phenoxy]-2-hydroxypropyl}acetamide;
2-[2,3-dimethyl-4-((6R,9aS)-2-{[6-(trifluoromethyl)pyridin-3-yl]-carbonyl}octahydro-2H-pyrido[1,2-a]pyrazin-6-yl)phenoxy]acetamide;
2-[2,3-dimethyl-4-((6R,9aS)-2-{[6-(trifluoromethyl)pyridin-3-yl]-carbonyl}octahydro-2H-pyrido[1,2-a]pyrazin-6-yl)phenoxy]-N-methylacetamide;
2-[2,3-dimethyl-4-((6R,9aS)-2-{[6-(trifluoromethyl)pyridin-3-yl]-carbonyl}octahydro-2H-pyrido[1,2-a]pyrazin-6-yl)phenoxy]-N-ethylacetamide;
2-[2,3-dimethyl-4-((6R,9aS)-2-{[6-(trifluoromethyl)pyridin-3-yl]-carbonyl}octahydro-2H-pyrido[1,2-a]pyrazin-6-yl)phenoxy]-N,N-dimethylacetamide;
N-Acetyl-N-(3-{2,3-dimethyl-4-[2-(6-trifluoromethyl-pyridine-3-carbonyl)-octahydro-pyrido-[1,2-a]pyrazin-6-yl]-phenoxy}-propyl)-acetamide;
N-{3-[2,3-dimethyl-4-((6R,9aS)-2-{[6-(trifluoromethyl)pyridin-3-yl]-carbonyl}octahydro-2H-pyrido-[1,2-a]pyrazin-6-yl)-phenoxy]propyl}acetamide;
(6R,9aS)-6-[4-(methoxymethoxy)-2,3-dimethylphenyl]-2-{[6-(trifluoromethyl)pyridin-3-yl]-carbonyl}octahydro-2H-pyrido-[1,2-a]pyrazine;
(2R)-1-[2,3-dimethyl-4-((6R,9aS)-2-{[6-(trifluoromethyl)pyridin-3-yl]carbonyl}octahydro-2H-pyrido[1,2-a]pyrazin-6-yl)-phenoxy]propan-2-ol;
2-(4-{(6R,9aS)-2-[(5-chloro-2-thienyl)carbonyl]octahydro-2H-pyrido[1,2-a]pyrazin-6-yl}-2,3-dimethylphenoxy)ethanol;
1-[2,3-dimethyl-4-((6R,9aS)-2-{[6-(trifluoromethyl)pyridin-3-yl]carbonyl}octahydro-2H-pyrido[1,2-a]pyrazin-6-yl)phenoxy]-2-methylpropan-2-ol;
(6R,9aS)-6-[4-(difluoromethoxy)-2,3-dimethylphenyl]-2-{[6-(trifluoromethyl)pyridin-3-yl]-carbonyl}octahydro-2H-pyrido[1,2-a]pyrazine;
(2S)-1-[2,3-dimethyl-4-((6R,9aS)-2-{[6-(trifluoromethyl)pyridin-3-yl]carbonyl}octahydro-2H-pyrido[1,2-a]pyrazin-6-yl)phenoxy]propan-2-ol;
2-[2,3-dimethyl-4-((6R,9aS)-2-{[5-(trifluoromethyl)-2-thienyl]carbonyl}octahydro-2H-pyrido[1,2-a]pyrazin-6-yl)phenoxy]ethanol;
(2S)-1-[2,3-dimethyl-4-((6R,9aS)-2-{[6-(chloro)pyridin-3-yl]carbonyl}-octahydro-2H-pyrido[1,2-a]pyrazin-6-yl)phenoxy]propan-2-ol;
(2R)-1-[2,3-dimethyl-4-((6R,9aS)-2-{[6-(chloro)pyridin-3-yl]carbonyl}-octahydro-2H-pyrido[1,2-a]pyrazin-6-yl)phenoxy]propan-2-ol;
(6-chloropyridin-3-yl)((6R,9aS)-6-(4-(2-hydroxyethoxy)-2,3-dimethylphenyl)-hexahydro-1H-pyrido[1,2-a]pyrazin-2 (6H)-yl)methanone;
(6-Chloro-pyridin-3-yl)-{(6R,9aS)-6-[4-(2-hydroxy-2-methyl-propoxy)-2,3-dimethyl-phenyl]-octahydro-pyrido[1,2-a]pyrazin-2-yl}-methanone;
(6-chloropyridin-3-yl)((6R,9aS)-6-(4-(1,1-difluoro-2-hydroxyethoxy)-2,3-dimethylphenyl)-hexahydro-1H-pyrido[1,2-a]pyrazin-2 (6H)-yl)methanone;
{(6R,9aS)-6-[4-(2-Hydroxy-1-hydroxymethyl-ethoxy)-2,3-dimethylphenyl]-octahydro-pyrido-[1,2-a]pyrazin-2-yl}-(6-trifluoro-methyl-pyridin-3-yl)-methanone;
{(6R,9aS)-6-[4-(2-Hydroxy-1-hydroxymethyl-ethoxy)-2,3-dimethylphenyl]-octahydro-pyrido-[1,2-a]pyrazin-2-yl}-(6-chloro-pyridin-3-yl)-methanone;
3-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]-N-propylpropan-1-amine;
N-{3-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]propyl}-2-methylbutan-1-amine;
N-(cyclopropylmethyl)-3-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]propan-1-amine;
N-{3-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]propyl}-2-methylpropan-1-amine;
N-(cyclohexylmethyl)-3-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]propan-1-amine;
N-{3-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]propyl}-2,2-dimethylpropan-1-amine;
3-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]-N-(2-ethoxyethyl)propan-1-amine;
3-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]-N-(2-isopropoxyethyl)propan-1-amine;
N′
-{3-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]propyl}-N,N-dimethylethane-1,2-diamine;
N-{3-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]propyl}-cyclopropanamine;
N-{3-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]propyl}-cyclohexanamine;
N-{3-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]propyl}cyclobutanamine;
N-{3-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]propyl}cyclopentanamine;
N-{3-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]propyl}-4-methylcyclohexanamine;
N-{3-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]propyl}-2-methylcyclohexanamine;
3-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]-N-isopropylpropan-1-amine;
N-{3-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]propyl}butan-2-amine;
N-{3-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]propyl}-3-methylbutan-2-amine;
3-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]-N-(2-methoxy-1-methylethyl)propan-1-amine;
N-(tert-butyl)-3-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]-piperazin-1-yl}ethyl)phenoxy]-propan-1-amine;
N2-{3-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]propyl}-N′
,N′
-dimethylpropane-1,2-diamine;
3-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]-N,N-diethylpropan-1-amine;
3-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]-N-methyl-N-propylpropan-1-amine;
N-{3-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]propyl}-N-methylbutan-1-amine;
3-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]-N-ethyl-N-isopropylpropan-1-amine;
3-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]-N,N-dipropylpropan-1-amine;
3-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]-N,N-dimethylpropan-1-amine;
3-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]-N-isopropyl-N-methylpropan-1-amine;
N-{3-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]propyl}-N-methylcyclohexanamine;
N-{3-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]propyl}-N-ethylcyclohexanamine;
3-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]-N,N-diisopropylpropan-1-amine;
N-{2-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]ethyl}propan-1-amine;
N-{2-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]ethyl}-2-methylbutan-1-amine;
N-(cyclopropylmethyl)-2-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]ethanamine;
N-{2-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]ethyl}-2-methylpropan-1-amine;
N-(cyclohexylmethyl)-2-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]ethanamine;
N-{2-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]ethyl}-2,2-dimethylpropan-1-amine;
2-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]-N-(2-ethoxyethyl)ethanamine;
2-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]-N-(2-isopropoxyethyl)ethanamine;
N′
-{2-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]ethyl}-N,N-dimethylethane-1,2-diamine;
N-{2-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]ethyl}-cyclopropanamine;
N-{2-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]ethyl}cyclohexanamine;
N-{2-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]ethyl}cyclobutanamine;
N-{2-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]ethyl}cyclopentanamine;
N-{2-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]ethyl}-4-methylcyclohexanamine;
N-{2-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]ethyl}-2-methylcyclohexanamine;
N-{2-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]ethyl}propan-2-amine;
N-{2-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]ethyl}butan-2-amine;
N-{2-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]ethyl}-3-methylbutan-2-amine;
N-{2-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]ethyl}-1-methoxypropan-2-amine;
N-{2-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]ethyl}-2-methylpropan-2-amine;
N2-{2-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]ethyl}-N1,N1-dimethylpropane-1,2-diamine;
2-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]-N,N-diethylethanamine;
N-{2-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]ethyl}-N-methylpropan-1-amine;
N-{2-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]ethyl}-N-methylbutan-1-amine;
N-{2-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]ethyl}-N-ethylpropan-2-amine;
N-{2-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]ethyl}-N-propylpropan-1-amine;
2-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]-N,N-dimethylethanamine;
N-{2-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]ethyl}-N-methylpropan-2-amine;
N-{2-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]ethyl}-N-methylcyclohexanamine;
N-{2-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]ethyl}-N-ethylcyclohexanamine;
N-{2-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]ethyl}-N-isopropylpropan-2-amine;
4-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]-N-propylbutan-1-amine;
N-{4-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]butyl}-2-methylbutan-1-amine;
N-(cyclopropylmethyl)-4-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]butan-1-amine;
4-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]-N-isobutylbutan-1-amine;
N-(cyclohexylmethyl)-4-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]butan-1-amine;
N-(2,2-dimethylpropyl)-4-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]butan-1-amine;
4-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]-N-(2-ethoxyethyl)butan-1-amine;
4-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]-N-(2-isopropoxyethyl)butan-1-amine;
N′
-{4-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]butyl}-N,N-dimethylethane-1,2-diamine;
N-{4-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]butyl}cyclopropanamine;
N-{4-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]butyl}cyclohexanamine;
N-{4-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]butyl}cyclobutanamine;
N-{4-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]butyl}cyclopentanamine;
N-{4-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]butyl}-4-methylcyclohexanamine;
N-{4-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]butyl}-2-methylcyclohexanamine;
4-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]-N-isopropylbutan-1-amine;
N-(sec-butyl)-4-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]butan-1-amine;
N-(1,2-dimethylpropyl)-4-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]butan-1-amine;
4-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]-N-(2-methoxy-1-methylethyl)butan-1-amine;
N-(tert-butyl)-4-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]butan-1-amine;
N2-{4-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]butyl}-N′
,N′
-dimethylpropane-1,2-diamine;
4-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]-N,N-diethylbutan-1-amine;
4-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]-N-methyl-N-propylbutan-1-amine;
N-butyl-4-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]-N-methylbutan-1-amine;
4-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]-N-ethyl-N-isopropylbutan-1-amine;
4-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]-N,N-dipropylbutan-1-amine;
4-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]-N,N-dimethylbutan-1-amine;
4-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]-N-isopropyl-N-methylbutan-1-amine;
N-{4-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]butyl}-N-methylcyclohexanamine;
N-{4-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]butyl}-N-ethylcyclohexanamine;
4-[2,3-dimethyl-4-(1-{4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl}ethyl)phenoxy]-N,N-diisopropylbutan-1-amine;
(6R,9aS)-2-(4-chloro-3-methoxyphenyl)-6-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]octahydro-2H-pyrido[1,2-a]pyrazine;
3-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}-N-ethylpropan-1-amine;
3-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}-N,N-dimethylpropan-1-amine;
3-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}-N-isopropylpropan-1-amine;
(6R,9aS)-2-(4-chloro-3-methoxyphenyl)-6-[4-(3-methoxypropoxy)-2,3-dimethylphenyl]octahydro-2H-pyrido[1,2-a]pyrazine;
(6R,9aS)-2-(4-chloro-3-methoxyphenyl)-6-{4-[2-ethoxy-1-(ethoxymethyl)ethoxy]-2,3-dimethylphenyl}octahydro-2H-pyrido[1,2-a]pyrazine;
4-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}butanenitrile;
(6R,9aS)-2-(4-chloro-3-methoxyphenyl)-6-{2,3-dimethyl-4-[3-(methylsulfonyl)propoxy]-phenyl}octahydro-2H-pyrido-[1,2-a]pyrazine;
2-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}acetamide;
4-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2-methoxyphenoxy}butanenitrile;
3-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2-methoxyphenoxy}-N,N-dimethylpropan-1-amine;
3-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2-methoxyphenoxy}-N-isopropylpropan-1-amine;
3-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2-methoxyphenoxy}-N-methylpropan-1-amine;
(6R,9aS)-2-(4-chloro-3-methoxyphenyl)-6-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]octahydro-8H-pyrido[1,2-a]pyrazin-8-one;
(6R,9aS)-2-(4-chloro-3-methoxyphenyl)-6-[3-methoxy-4-(2-methoxyethoxy)phenyl]octa-hydro-2H-pyrido[1,2-a]pyrazine;
3-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}-N,N-bis(2-methoxyethyl)propan-1-amine;
3-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}-N-(2-methoxyethyl)propan-1-amine;
N-(3-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}propyl)-N-(2-methoxyethyl)acetamide;
methyl {4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}acetate;
1-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}-2-methylpropan-2-ol;
(6R,9aS)-2-(4-chloro-3-methoxyphenyl)-6-(4-isobutoxy-2,3-dimethylphenyl)octahydro-2H-pyrido[1,2-a]pyrazine;
2-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}-N-(2-methoxyethyl)acetamide;
(6R,9aS)-2-(4-chloro-3-methoxyphenyl)-6-{4-[2-(2-methoxyethoxy)ethoxy]-2,3-dimethylphenyl}octahydro-2H-pyrido[1,2-a]pyrazine;
2-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}-N-methylacetamide;
2-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}-N,N-dimethylacetamide;
{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}acetonitrile;
2-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}ethanimidamide;
(6R,9aS)-2-(4-chloro-3-methoxyphenyl)-6-[4-(cyclopropylmethoxy)-2,3-dimethylphenyl]octahydro-2H-pyrido[1,2-a]pyrazine;
3-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}-N-methoxy-N-methylpropan-1-amine;
3-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}-N-methoxypropan-1-amine;
4-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}-N,N-dimethylbutanamide;
2-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}-N-ethyl-N-methylacetamide;
2-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}-N-methyl-N-propylacetamide;
N-butyl-2-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}-N-methylacetamide;
2-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}propanenitrile;
(6R,9aS)-2-(4-chloro-3-methoxyphenyl)-6-[4-(2-isopropoxyethoxy)-2,3-dimethylphenyl]octahydro-2H-pyrido[1,2-a]pyrazine;
(6R,9aS)-2-(4-chloro-3-methoxyphenyl)-6-(3-methoxy-4-propoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazine;
4-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}butanamide;
4-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}-N-methylbutanamide;
N-(3-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}propyl)-2-methoxyacetamide;
N-(3-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}propyl)methane-sulfonamide;
N-(3-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}propyl)acetamide;
2-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}-N-methoxyacetamide;
2-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}-N-[2-(dimethylamino)ethyl]acetamide;
{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}acetic acid;
2-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}-N-ethylacetamide;
1-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}-3-[(2-methoxyethyl)amino]propan-2-ol;
1-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}-3-[(2-methoxyethyl)(methyl)amino]propan-2-ol;
1-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}-3-(cyclopropylamino)propan-2-ol;
N-(3-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}propyl)-propanamide;
N-(3-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}propyl)-2-methylpropanamide;
N-(3-{4-[(6R,9aS)-2-(4-Chloro-3-methoxy-phenyl)-octahydro-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}-propyl)-N-isobutyryl-isobutyramide;
N-(3-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}propyl)-2,2-dimethylpropanamide;
N-(3-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}propyl)-formamide;
3-{4-[2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}propan-1-ol;
N-(2-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}ethyl)acetamide;
(6R,9aS)-2-(4-fluoro-3-methoxy-phenyl)-6-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]octahydro-2H-pyrido[1,2-a]pyrazine;
N-(3-{4-[(6R,9aS)-2-(4-fluoro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}propyl)acetamide;
2-{4-[(6R,9aS)-2-(4-fluoro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}-N,N-dimethylacetamide;
1-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}acetone;
3-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}-2,2-dimethylpropan-1-ol;
(6R,9aS)-2-(4-fluoro-3-methoxyphenyl)-6-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]octahydro-2H-pyrido[1,2-a]pyrazine;
1-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}-3,3-dimethylbutan-2-one;
2-{4-[(6R,9aS)-2-(4-fluoro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}-N,N-dimethylacetamide;
N-ethyl-2-{4-[(6R,9aS)-2-(4-fluoro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}acetamide;
2-{4-[(6R,9aS)-2-(4-fluoro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}-N-methylacetamide;
2-{4-[(6R,9aS)-2-(4-fluoro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}acetamide 3-{4-[(6R,9aS)-2-(4-fluoro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}propan-1-ol;
3-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}propan-1-ol;
(2Z)-1-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}-3,3-dimethylbutan-2-one oxime;
2-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}ethanol;
2-{4-[(6R,9aS)-2-(4-fluoro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}ethanol;
(2R)-1-amino-3-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}propan-2-ol;
(2S)-1-amino-3-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}propan-2-ol;
N-((2R)-3-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}-2-hydroxypropyl)acetamide;
N-((2S)-3-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}-2-hydroxypropyl)acetamide;
(1R)-2-(acetylamino)-1-({4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}methyl)ethyl acetate;
(1S)-2-(acetylamino)-1-({4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}methyl)ethyl acetate;
4-{4-[(6R,9aS)-2-(4-fluoro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}butanoic acid;
4-{4-[(6R,9aS)-2-(4-fluoro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}butanamide;
4-{4-[(6R,9aS)-2-(4-fluoro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}-N-methylbutanamide;
4-{4-[(6R,9aS)-2-(4-fluoro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}-N,N-dimethylbutanamide;
1-{4-[(6R,9aS)-2-(4-fluoro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}acetone;
1-{4-[(6R,9aS)-2-(4-fluoro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}propan-2-ol;
(2E)-1-{4-[(6R,9aS)-2-(4-fluoro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}acetone oxime;
N-(3-{4-[(6R,9aS)-2-(4-fluoro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}propyl)acetamide;
(2E)-1-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}acetone oxime;
(2E)-1-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}acetone O-methyloxime;
N-(3-{4-[(6R,9aS)-2-(4-chloro-3-methoxyphenyl)octahydro-2H-pyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy}propyl)-N-methylacetamide;
2-(4-{[4-(4-chloro-3-methoxyphenyl)piperazin-1-yl]methyl}-2-methoxyphenoxy)-N,N-dimethylethanamine;
2-(4-{1-[4-(4-chloro-3-methoxyphenyl)piperazin-1-yl]ethyl}-2-methoxyphenoxy)-N,N-dimethylethanamine;
2-(2-chloro-5-{4-[1-(3,4-dimethoxyphenyl)ethyl]piperazin-1-yl}phenoxy)-N,N-dimethylethanamine;
3-(2-chloro-5-{4-[1-(3,4-dimethoxyphenyl)ethyl]piperazin-1-yl}phenoxy)-N,N-dimethylpropan-1-amine;
ethyl 4-(4-{[4-(4-chloro-3-methoxyphenyl)piperazin-1-yl]methyl}-2-methoxyphenoxy)butanoate;
6-{[4-(4-chloro-3-methoxyphenyl)piperazin-1-yl]methyl}-2H-chromen-2-one;
1-(4-chloro-3-methoxyphenyl)-4-{1-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]ethyl}piperazine;
1-(4-chloro-3-methoxyphenyl)-4-{(1R)-1-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]ethyl}piperazine;
1-(4-chloro-3-methoxyphenyl)-4-{(1S)-1-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]ethyl}piperazine;
3-(4-{1-[4-(4-chloro-3-methoxyphenyl)piperazin-1-yl]ethyl}-2,3-dimethylphenoxy)-N-methylpropan-1-amine;
3-(4-{1-[4-(4-chloro-3-methoxyphenyl)piperazin-1-yl]ethyl}-2,3-dimethylphenoxy)-N-ethylpropan-1-amine;
3-(4-{1-[4-(4-chloro-3-methoxyphenyl)piperazin-1-yl]ethyl}-2,3-dimethylphenoxy)-N-(cyclopropylmethyl)propan-1-amine;
3-(4-{1-[4-(4-chloro-3-methoxyphenyl)piperazin-1-yl]ethyl}-2,3-dimethylphenoxy)-N-(2-methoxyethyl)propan-1-amine;
3-(4-{1-[4-(4-chloro-3-methoxyphenyl)piperazin-1-yl]ethyl}-2,3-dimethylphenoxy)-N-isopropylpropan-1-amine;
N-[3-(4-{1-[4-(4-chloro-3-methoxyphenyl)piperazin-1-yl]ethyl}-2,3-dimethylphenoxy)propyl]cyclopentanamine;
3-(4-{1-[4-(4-chloro-3-methoxyphenyl)piperazin-1-yl]ethyl}-2,3-dimethylphenoxy)-N,N-dimethylpropan-1-amine;
1-(4-chloro-3-methoxyphenyl)-4-{1-[4-(cyclopropylmethoxy)-2,3-dimethylphenyl]ethyl)}piperazine;
1-(4-chloro-3-methoxyphenyl)-4-{1-[4-(3-ethoxypropoxy)-2,3-dimethylphenyl]ethyl}piperazine;
3-(4-{1-[4-(4-chloro-3-methoxyphenyl)piperazin-1-yl]ethyl}-2-methoxyphenoxy)-N-isopropylpropan-1-amine;
1-[1-(4-butoxy-3-methoxyphenyl)ethyl]-4-(4-chloro-3-methoxyphenyl)piperazine;
1-(4-chloro-3-methoxyphenyl)-4-{1-[4-(cyclopropylmethoxy)-3-methoxyphenyl]ethyl}piperazine;
1-[1-(4-butoxy-2,3-dimethylphenyl)ethyl]-4-(4-chloro-3-methoxyphenyl)piperazine;
1-(4-chloro-3-methoxyphenyl)-4-{1-[3-methoxy-4-(2-methoxyethoxy)phenyl]ethyl}piperazine;
2-(4-{1-[4-(4-chloro-3-methoxyphenyl)piperazin-1-yl]ethyl}-2,3-dimethylphenoxy)acetamide;
(4-{1-[4-(4-chloro-3-methoxyphenyl)piperazin-1-yl]ethyl}-2,3-dimethylphenoxy)acetonitrile;
4-(4-{1-[4-(4-chloro-3-methoxyphenyl)piperazin-1-yl]ethyl}-2,3-dimethylphenoxy)butanenitrile;
1-(4-bromo-3-methoxyphenyl)-4-{1-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]ethyl}piperazine;
1-{1-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]ethyl}4-(3-methoxy-4-methylphenyl)piperazine;
1-(2,3-dihydro-1-benzofuran-6-yl)-4-{1-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]ethyl}piperazine;
1-{1-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]ethyl}-4-(3-methoxyphenyl)piperazine;
1-{1-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]ethyl}-4-(3-methoxy-4-vinylphenyl)piperazine;
1-(3,4-difluoro-5-methoxyphenyl)-4-{1-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]ethyl}piperazine;
3-(4-{1-[4-(4-chloro-3-methoxyphenyl)piperazin-1-yl]ethyl}-2,3-dimethylphenoxy)-N-methoxypropan-1-amine;
2-(4-{[3-(4-Chloro-3-methoxyphenyl)-3-hydroxy-8-azabicyclo[3.2.1]oct-8-yl]methyl}-2,3-dimethylphenoxy)-N,N-dimethylacetamide;
2-(4-{[3-(4-Chloro-3-methoxyphenyl)-3-hydroxy-8-azabicyclo[3.2.1]oct-8-yl]methyl}-2,3-dimethylphenoxy)-N-methylacetamide;
3-(4-Chloro-3-methoxyphenyl)-8-{4-[3-(dimethylamino)propoxy]-2,3-dimethylbenzyl}-8-azabicyclo[3.2.1]octan-3-ol;
3-(4-Chloro-3-methoxyphenyl)-8-[4-(3-hydroxypropoxy)-2,3-dimethylbenzyl]-8-azabicyclo[3.2.1]octan-3-ol;
3-(4-Chloro-3-methoxyphenyl)-8-[4-(2-methoxyethoxy)-2,3-dimethylbenzyl]-8-azabicyclo[3.2.1]octan-3-ol;
or3-(4-Chloro-3-methoxyphenyl)-8-[4-(2-hydroxyethoxy)-2,3-dimethylbenzyl]-8-azabicyclo[3.2.1]octan-3-ol.
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6. A compound or salt of claim 3, wherein V is absent.
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4-5. -5. (canceled)
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9-13. -13. (canceled)
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17-19. -19. (canceled)
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24-25. -25. (canceled)
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27-28. -28. (canceled)
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31-33. -33. (canceled)
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35-40. -40. (canceled)
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42-44. -44. (canceled)
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46-48. -48. (canceled)
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51. (canceled)
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53-54. -54. (canceled)
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57-67. -67. (canceled)
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69-83. -83. (canceled)
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85. (canceled)
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87-90. -90. (canceled)
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95-97. -97. (canceled)
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100-103. -103. (canceled)
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105-115. -115. (canceled)
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126-130. -130. (canceled)
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132-134. -134. (canceled)
Specification
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Current AssigneeNeurogen Corporation (Ligand Pharmaceuticals, Inc.)
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Original AssigneeNeurogen Corporation (Ligand Pharmaceuticals, Inc.)
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InventorsLee, Kyungae, Yoon, Taeyoung, Chenard, Bertrand L., Doller, Dario, Li, Guiying, Hodgetts, Kevin J., Ghosh, Manuka, Luke, George P., Hutchinson, Alan J., Pringle, Wallace C., Peterson, John M., O'Donnell, Mary-Margaret E., Steenstra, Cheryl K., Tarrant, James G.
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Application NumberUS11/154,986Publication NumberTime in Patent OfficeDaysField of SearchUS Class Current514/249CPC Class CodesA61P 15/00 Drugs for genital or sexual...A61P 15/10 for impotenceA61P 15/12 for climacteric disordersA61P 3/00 Drugs for disorders of the ...A61P 3/04 Anorexiants; Antiobesity ag...A61P 3/10 for hyperglycaemia, e.g. an...A61P 43/00 Drugs for specific purposes...A61P 9/00 Drugs for disorders of the ...C07D 207/08 with hydrocarbon radicals, ...C07D 207/12 Oxygen or sulfur atomsC07D 207/26 2-PyrrolidonesC07D 207/38 2-PyrrolonesC07D 211/18 with substituted hydrocarbo...C07D 211/34 with hydrocarbon radicals, ...C07D 211/38 Halogen atoms or nitro radi...C07D 211/42 attached in position 3 or 5C07D 211/46 having a hydrogen atom as t...C07D 211/52 having an aryl radical as t...C07D 211/74 Oxygen atomsC07D 213/64 attached in position 2 or 6C07D 213/74 : Amino or imino radicals sub...C07D 213/82 : in position 3C07D 231/12 : with only hydrogen atoms, h...C07D 233/54 : having two double bonds bet...C07D 233/56 : with only hydrogen atoms or...C07D 249/04 : 1,2,3-Triazoles; Hydrogenat...C07D 249/08 : 1,2,4-Triazoles; Hydrogenat...C07D 257/04 : Five-membered ringsC07D 261/08 : with only hydrogen atoms, h...C07D 275/02 : not condensed with other ringsC07D 295/073 : with the ring nitrogen atom...C07D 295/088 : to an acyclic saturated chainC07D 295/096 : with the ring nitrogen atom...C07D 295/192 : from aromatic carboxylic acidsC07D 307/20 : Oxygen atomsC07D 307/79 : with only hydrogen atoms, h...C07D 307/82 : with hetero atoms or with c...C07D 309/06 : Radicals substituted by oxy...C07D 309/12 : only hydrogen atoms and one...C07D 311/14 : substituted in position 6 a...C07D 401/12 : linked by a chain containin...C07D 471/04 : Ortho-condensed systemsC07D 471/08 : Bridged systemsC07D 487/04 : Ortho-condensed systemsC07D 487/08 : Bridged systems