ES2556772T3 - Nicotinamidas sustituidas como moduladores de KCNQ2/3 - Google Patents

Nicotinamidas sustituidas como moduladores de KCNQ2/3 Download PDF

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ES2556772T3
ES2556772T3 ES10708139.0T ES10708139T ES2556772T3 ES 2556772 T3 ES2556772 T3 ES 2556772T3 ES 10708139 T ES10708139 T ES 10708139T ES 2556772 T3 ES2556772 T3 ES 2556772T3
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carboxylamide
pyridine
fluorophenyl
propylsulfanyl
methyl
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Sven KÜHNERT
Beatrix Merla
Gregor Bahrenberg
Wolfgang Schröder
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Grünenthal GmbH
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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Abstract

Nicotinamidas sustituidas de fórmula general**Fórmula** A1 representa CR10R11o S; A2 representa CR12R13, C(>=O) O, S, S(>=O)2; R1 represnta alquilo (C1-10) o heteroalquilo (C2-10) en cada caso saturado o insaturado, lineal o ramificado, sustituido de forma simple o múltiple o no sustituido; cicloalquilo (C3-10) o tererociclilo, en cada caso saturado o insaturado, sustituido de forma simple o múltiple o no sustituido; arilo o heteroarilo, en cada caso sustituido de forma simple o múltiple o no sustituido; cicloalquilo (C3-10) o heterociclilo unido a través de un alquilo (C1-8) o un heteroalquilo (C2-8), en cada caso saturado o insaturado, sustituido de forma simple o múltiple o no sustituido, pudiendo la cadena alquilo o hereroalquilo en cada caso ser lineal o ramificada, saturada o no saturada, sustituida de forma simple o múltiple o no sistituida; o arilo o heteroarilo unidos a través de un alquilo (C2-8), en cada caso sustituido de forma simple o múltiple o no sustituido, pudiendo la cadena alquilo o heteroalquilo en cada caso ser lienal o ramificada, saturada o insaturada, sustituida de forma simple o múltiple o no sustituida.

Description

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Tabla 2
Ej. decomp.
Designación química Síntesis análogaal ej. de comp. MD m/z[M+H]+
2
2-(3-ciclohexil-propilsulfanil)-N-(tiofen-2-ilmetil)piridin-3-carboxilamida 17 375,1
4
N-(tiofen-2-ilmetil)-2-[2-[3-(trifluorometil)fenoxi]etilsulfanil]piridin-3-carboxilamida 17 439,1
5
2-(4-metil-pentilsulfanil)-N-(tiofen-2-ilmetil)piridin-3-carboxilamida 17 335,1
7
2-(4-fenilbutil)-N-(tiofen-2-ilmetil)piridin-3-carboxilamida 13 351,1
8
2-[3-(bencenosulfonil)propil]-N-(ciclohexilmetil)piridin-3-carboxilamida 13 401,2
9
N-(ciclohexilmetil)-2-(4-fenilbutil)piridin-3-carboxilamida 13 351,2
10
2-[3-(bencenosulfonil)propil]-N-(tiofen-2-ilmetil)piridin-3-carboxilamida 13 401,1
12
N-(tiofen-2-ilmetil)-2-[3-[[3-(trifluorometil)fenil]sulfonil]propil]piridin-3-carboxilamida 13 469,1
18
N-(tiofen-2-ilmetil)-2-[3-[3-(trifluorometil)fenil]propilsulfanil]piridin-3-carboxilamida 17 437,1
19
2-[2-[(4-fluorofenil)sulfanil]propilsulfanil]-N-(tiofen-2-ilmetil)piridin-3-carboxilamida 16 (de VC002) 419,1
20
N-(tiofen-2-ilmetil)-2-[2-[[3-(trifluorometil)fenil]sulfanil]propilsulfanil]piridin-3-carboxilamida 16 (de VC003) 469,1
22
2-[4-(4-fluorofenil)butil]-N-(tiofen-2-ilmetil)piridin-3-carboxilamida 21 369,1
23
2-(3-fenilsulfanil-propil)-N-(tiofen-2-ilmetil)piridin-3-carboxilamida 21 369,1
24
2-[(1-metil-2-fenilsulfanil-etil)sulfanil]-N-(tiofen-2-ilmetil)piridin-3-carboxilamida 16 (de VC004) 401,1
25
N-(cicloheptilmetil)-2-[4-[3-(trifluorometil)fenil]butil]piridin-3-carboxilamida 17 433,2
26
N-(5-biciclo[2.2.1]heptanilmetil)-2-[4-[3-(trifluorometil)fenil]butil]piridin-3-carboxilamida 17 431,2
27
N-(5-biciclo[2.2.1]heptanilmetil)-2-[3-[3-(trifluorometil)fenil]propilsulfanil]piridin-3-carboxilamida 51 449,2
28
N-(5-biciclo[2.2.1]heptanilmetil)-2-(4-metil-pentilsulfanil)piridin-3-carboxilamida 51 347,2
29
N-(cicloheptilmetil)-2-[3-[(4-fluorofenil)sulfanil]propil]piridin-3-carboxilamida 21 401,2
30
N-(5-biciclo[2.2.1]heptanilmetil)-2-[3-[(4-fluorofenil)sulfanil]propil]piridin-3-carboxilamida 21 399,2
31
N-(cicloheptilmetil)-2-[3-[[3-(trifluorometil)fenil]sulfonil]propil]piridin-3-carboxilamida 21 483,2
32
N-(5-biciclo[2.2.1]heptanilmetil)-2-[3-[[3-(trifluorometil)fenil]sulfonil]propil]piridin-3-carboxilamida 21 481,2
33
N-(5-biciclo[2.2.1]heptanilmetil)-2-(3-fenil-propilsulfanil)piridin-3-carboxilamida 51 381,2
34
N-(5-biciclo[2.2.1]heptanilmetil)-2-[3-[4-(trifluorometil)fenil]propilsulfanil]piridin-3-carboxilamida 51 449,2
35
N-(5-biciclo[2.2.1]heptanilmetil)-2-[3-(4-clorofenil)propilsulfanil]piridin-3-carboxilamida 51 415,2
36
N-[(3,5-difluorofenil)metil]-2-[3-(4-fluorofenil)propilsulfanil]piridin-3-carboxilamida 42 417,1
37
N-[(5-clorotiofen-2-il)metil]-2-[3-(4-fluorofenil)propilsulfanil]piridin-3-carboxilamida 42 421,1
38
N-[(2,2-dimetil-ciclopropil)metil]-2-[3-(4-fluorofenil)propilsulfanil]piridin-3-carboxilamida 42 373,2
39
N-(5-biciclo[2.2.1]heptanilmetil)-2-[3-(3-fluorofenil)propilsulfanil]piridin-3-carboxilamida 51 399,2
40
N-(ciclohexilmetil)-2-[3-(4-fluorofenil)propilsulfanil]piridin-3-carboxilamida 42 387,2
41
N-(cicloheptilmetil)-2-[3-(4-fluorofenil)propilsulfanil]piridin-3-carboxilamida 42 401,2
43
N-(5-biciclo[2.2.1]heptanilmetil)-2-[[3-(4-fluorofenil)-3-oxopropil]sulfanil]piridin-3-carboxilamida 51 413,2
44
N-(5-biciclo[2.2.1]heptanilmetil)-2-[(3-oxo-3-fenilpropil)sulfanil]piridin-3-carboxilamida 51 395,2
45
N-(5-biciclo[2.2.1]heptanilmetil)-2-(hexilsulfanil)piridin-3-carboxilamida 51 347,2
46
N-(5-biciclo[2.2.1]heptanilmetil)-2-(2-fenoxi-etilsulfanil)piridin-3-carboxilamida 51 383,2
Ej. decomp.
Designación química Síntesis análogaal ej. de comp. MD m/z[M+H]+
47
N-(5-biciclo[2.2.1]heptanilmetil)-2-[2-[3-(trifluorometil)fenoxi]etilsulfanil]piridin-3-carboxilamida 51 451,2
48
2-[3-(4-fluorofenil)propilsulfanil]-N-(3,3,3-trifluoropropil)piridin-3-carboxilamida 51 387,1
49
N-(5-biciclo[2.2.1]heptanilmetil)-2-[2-(4-fluorofenoxi)etilsulfanil]piridin-3-carboxilamida 51 401,2
52
N-(5-biciclo[2.2.1]heptanilmetil)-2-(3-naftalen-1-il-propilsulfanil)piridin-3-carboxilamida 51 431,2
53
N-(5-biciclo[2.2.1]heptanilmetil)-2-[3-[3-fluor-4-(trifluorometil)fenil]propilsulfanil]piridin-3-carboxilamida 51 467,2
54
N-(5-biciclo[2.2.1]heptanilmetil)-2-[3-[4-fluor-3-(trifluorometil)fenil]propilsulfanil]piridin-3-carboxilamida 51 467,2
55
N-(ciclooctilmetil)-2-[3-(4-fluorofenil)propilsulfanil]piridin-3-carboxilamida 42 415,2
56
N-(5-biciclo[2.2.1]heptanilmetil)-2-[3-(4-metoxifenil)propilsulfanil]piridin-3-carboxilamida 51 411,2
57
2-[3-(4-fluorofenil)propilsulfanil]-N-[(4-metoxifenil)metil]piridin-3-carboxilamida 42 411,1
59
2-[3-(4-fluorofenil)propilsulfanil]-N-[[3-(trifluorometil)fenil]metil]piridin-3-car oxilamida 42 449,1
60
N-(5-biciclo[2.2.1]heptanilmetil)-2-[3-(3,4-difluorofenil)propilsulfanil]piridin-3-carboxilamida 51 417,2
61
N-(5-biciclo[2.2.1]heptanilmetil)-2-[3-(3,5-difluorofenil)propilsulfanil]pir n-3-carboxilamida 51 417,2
62
N-(5-biciclo[2.2.1]heptanilmetil)-2-[3-(2,4-difluorofenil)propilsulfanil]piridin-3-carboxilamida 51 417,2
63
N-[(2-fluorofenil)metil]-2-[3-(4-fluorofenil)propilsulfanil]piridin-3-carboxilamida 42 399,1
64
N-[(3-fluorofenil)metil]-2-(3-(4-fluorofenil)propilsulfanil]piridin-3-carboxilamida 42 399,1
65
N-[(4-fluorofenil)metil]-2-[3-(4-fluorofenil)propilsulfanil]piridin-3-carboxilamida 42 399,1
66
N-bencil-2-[3-(4-fluorofenil)propilsulfanil]piridin-3-carboxilamida 42 381,1
67
N-(5-biciclo[2.2.1]heptanilmetil)-2-[(1-metil-3-fenilpropil)sulfanil]piridin-3-carboxilamida 51 395,2
68
N-(5-biciclo[2.2.1]heptanilmetil)-2-[3-(3,4,5-trifluorofenil)propilsulfanil]piridin-3-carboxilamida 51 435,2
69
N-(5-biciclo[2.2.1]heptanilmetil)-2-[3-[3-fluor-5-(trifluorometil)fenil]propilsulfanil]piridin-3-carboxilamida 51 467,2
70
N-(5-biciclo[2.2.1]heptanilmetil)-2-[3-(3-metoxifenil)propilsulfanil]piridin-3-carboxilamida 51 411,2
71
N-[(3,4-difluorofenil)metil]-2-[3-(4-fluorofenil)propilsulfanil]piridin-3-carboxilamida 42 417,1
72
N-(2,3-dihidrobenzofuran-5-ilmetil)-2-[3-(4-fluorofenil)propilsulfanil]piridin-3-carboxilamida 42 423,1
73
N-(5-biciclo[2.2.1]heptanilmetil)-2-[3-(3-hidroxifenil)propilsulfanil]piridin-3-carboxilamida 58 397,2
74
N-(5-biciclo[2.2.1]heptanilmetil)-2-[[3-(4-fluorofenil)-1-metilpropil]sulfanil]piridin-3-carboxilamida 51 413,2
75
N-(5-biciclo[2.2.1]heptanilmetil)-2-[[3-(4-fluorofenil)-2-metilpropil]sulfanil]piridin-3-carboxilamida 51 413,2
76
2-[3-(4-fluorofenil)propilsulfanil]-N-[(2-metoxifenil)metil]piridin-3-carboxilamida 42 411,1
77
2-[3-(4-fluorofenil)propilsulfanil]-N-[(3-metoxifenil)metil]piridin-3-carboxilamida 42 411,1
78
2-[3-(4-fluorofenil)propilsulfanil]-N-fenetilpiridin-3-carboxilamida 42 395,2
79
2-[3-(4-fluorofenil)propilsulfanil]-N-[[4-(trifluorometiloxi)fenil]metil]piridin-3-carboxilamida 42 465,1
80
2-[3-(4-fluorofenil)propilsulfanil]-N-[[4-(trifluorometil)fenil]metil]piridin-3-carboxilamida 42 449,1
81
2-[3-(4-fluorofenil)propilsulfanil]-N-(2-piridin-3-iletil)piridin-3-carboxilam 42 396,1
82
2-[3-(4-fluorofenil)propilsulfanil]-N-(2-piridin-2-iletil)piridin-3-carboxilamida 42 396,1
83
2-[3-(4-fluorofenil)propilsulfanil]-N-[(2-hidroxifenil)metil]piridin-3-carboxilamida 58 397,1
84
2-[3-(4-fluorofenil)propilsulfanil]-N-[(3-hidroxifenil)metil]piridin-3-carboxilamida 58 397,1
85
2-[3-(4-fluorofenil)propilsulfanil]-N-[2-(m-tolil)etil]piridin-3-carboxilamida 42 409,2
imagen33
imagen34
Ej. de comp.
Designación química Síntesis análoga al ej. de comp. MD m/z [M+H]+
86
2-[3-(4-fluorofenil)propilsulfanil]-N-[2-(o-tolil)etil]piridin-3-carboxilamida 42 409,2
87
2-[3-(4-fluorofenil)propilsulfanil]-N-[[3-(trifluorometiloxi)fenil]metil]piridin-3-carboxilamida 42 465,1
88
2-[3-(4-fluorofenil)propilsulfanil]-N-[(4-hidroxifenil)metil]piridin-3-carboxilamida 42 397,1
89
2-[3-(4-fluorofenil)propilsulfanil]-N-(2-piridin-4-iletil)piridin-3-carboxilamida 42 396,1
90
2-[3-(4-fluorofenil)propilsulfanil]-N-[2-(p-tolil)etil]piridin-3-carboxilamida 42 409,2
91
N-(5-biciclo[2.2.1]heptanilmetil)-2-[3-(4-fluorofenil)butilsulfanil]piridin-3-carboxilamida 51 413,2
92
N-(5-biciclo[2.2.1]heptanilmetil)-2-[3-(2,4,5-trifluorofenil)propilsulfanil]piridin-3-carboxilamida 51 435,2
93
2-[3-(4-fluorofenil)propilsulfanil]-N-(3-piridin-2-ilpropil)piridin-3-carboxilamida 42 410,2
94
2-[3-(4-fluorofenil)propilsulfanil]-N-(3-piridin-3-ilpropil)piridin-3-carboxilamida 42 410,2
95
2-[3-(4-fluorofenil)propilsulfanil]-N-(3-piridin-4-ilpropil)piridin-3-carboxilamida 42 410,2
96
2-[3-(4-fluorofenil)propilsulfanil]-N-propilpiridin-3-carboxilamida 42 333,1
97
N-butil-2-[3-(4-fluorofenil)propilsulfanil]piridin-3-carboxilamida 42 347,2
98
2-(3-piridin-3-il-propilsulfanil)-N-(tiofen-2-ilmetil)piridin-3-carboxilamida 167 370,1
99
2-[3-(p-tolil)propilsulfanil]-N-(tiofen-2-ilmetil)piridin-3-carboxilamida 167 383,1
100
2-(4-fenil-butilsulfanil)-N-(tiofen-2-ilmetil)piridin-3-carboxilamida 51 383,1
101
2-(3-piridin-4-il-propilsulfanil)-N-(tiofen-2-ilmetil)piridin-3-carboxilamida 51 370,1
102
2-(3-naftalen-2-il-propilsulfanil)-N-(tiofen-2-ilmetil)piridin-3-carboxilamida 51 419,1
103
2-[3-(m-tolil)propilsulfanil]-N-(tiofen-2-ilmetil)piridin-3-carboxilamida 167 383,1
104
N-(tiofen-2-ilmetil)-2-(3-tiofen-2-il-propilsulfanil)piridin-3-carboxilamida 167 375,1
105
2-[(1-metil-3-fenilpropil)sulfanil]-N-(tiofen-2-ilmetil)piridin-3-carboxilamida 51 383,1
106
N-(tiofen-2-ilmetil)-2-(3-tiofen-3-il-propilsulfanil)piridin-3-carboxilamida 167 375,1
107
2-[[1-metil-3-[3-(trifluorometil)fenil]propil]sulfanil]-N-(tiofen-2-ilmetil)piridin-3-carboxilamida 167 451,1
108
2-[(2-bencilciclohexil)sulfanil]-N-(tiofen-2-ilmetil)piridin-3-carboxilamida 115 423,1
109
2-[3-[3-metil-5-(trifluorometil)fenil]propilsulfanil]-N-(tiofen-2-ilmetil)piridin-3-carboxilamida 115 451,1
110
2-[4-(3,4-difluorofenil)butilsulfanil]-N-(tiofen-2-ilmetil)piridin-3-carboxilamida 115 419,1
111
2-(3-piridin-2-il-propilsulfanil)-N-(tiofen-2-ilmetil)piridin-3-carboxilamida 225 370,1
113
2-[3-[4-metil-3-(trifluorometil)fenil]propilsulfanil]-N-(tiofen-2-ilmetil)piridin-3-carboxilamida 115 451,1
114
2-[(3-fenilciclohexil)sulfanil]-N-(tiofen-2-ilmetil)piridin-3-carboxilamida 115 409,1
116
2-[[3,3-difluor-3-(4-fluorofenil)propil]sulfanil]-N-(3,3-dimetilbutil)piridin-3-carboxilamida 115 411,2
117
N-(cicloheptilmetil)-2-[[3,3-difluor-3-(4-fluorofenil)propil]sulfanil]piridin-3-carboxilamida 115 437,2
118
2-[[3,3-difluor-3-(4-fluorofenil)propil]sulfanil]-N-(tiofen-2-ilmetil)piridin-3-carboxilamida 115 423,1
119
2-[3-(4-fluorofenil)propilsulfanil]-N-(1,2,3,4-tetrahidronaftalen-2-ilmetil)piridin-3-carboxilamida 169 435,2
120
N-(2,3-dihidro-1H-inden-2-il-metil)-2-[3-(4-fluorofenil)propilsulfanil]piridin-3-carboxilamida 169 421,2
121
N-(1,3-benzodioxol-5-ilmetil)-2-[3-(4-fluorofenil)propilsulfanil]piridin-3-carboxilamida 169 425,1
122
2-[3-(4-fluorofenil)propilsulfanil]-N-[(3-fenilfenil)metil]piridin-3-carboxilamida 169 457,2
123
2-[3-(4-fluorofenil)propilsulfanil]-N-[(3-metilciclohexil)metil]piridin-3-carboxilamida 169 401,2
imagen35
Ej. decomp.
Designación química Síntesis análogaal ej. de comp. MD m/z[M+H]+
124
2-[[3,3-difluor-3-(4-fluorofenil)propil]sulfanil]-N-[(4-fluorofenil)metil]piridin-3-carboxilamida 115 435,1
125
N-(3,3-dimetil-2-oxobutil)-2-[3-(4-fluorofenil)propilsulfanil]piridin-3-carboxilamida 169 389,2
127
2-[3-(4-fluorofenil)propilsulfanil]-N-(piridin-3-ilmetil)piridin-3-carboxilamida 169 382,1
128
2-[3-(4-fluorofenil)propilsulfanil]-N-(piridin-4-ilmetil)piridin-3-carboxilam 169 382,1
129
3-[[[2-[3-(4-fluorofenil)propilsulfanil]piridin-3-carbonil]amino]metil]benzoato de metilo 169 439,1
130
2-[3-(4-fluorofenil)propilsulfanil]-N-[3-(2-metoxifenil)propil]piridin-3-carb mida 169 439,2
132
N-[(4-fluorofenil)metil]-2-[[1-metil-3-[3-(trifluorometil)fenil]propil]sulfanil]piridin-3-carboxilamida 51 463,1
133
2-[3-(4-fluorofenil)propilsulfanil]-N-(3-metilbutil)piridin-3-carboxilamida 169 361,2
134
2-[3-(4-fluorofenil)propilsulfanil]-N-(tetrahidropiran-2-ilmetil)piridin-3-carboxilamida 169 389,2
135
2-[3-(4-fluorofenil)propilsulfanil]-N-[3-(1H-pirazol-1-il)propil]piridin-3-carboxilamida 169 399,2
136
2-[3-(4-fluorofenil)propilsulfanil]-N-(naftalen-2-ilmetil)piridin-3-carboxilamida 169 431,2
137
N-(2,3-dihidro-[1,4]benzodioxin-6-ilmetil)-2-[3-(4-fluorofenil)propilsulfanil]piridin-3-carboxilamida 169 439,1
138
2-[3-(4-fluorofenil)propilsulfanil]-N-[(3-morfolin-4-ilfenil)metil]piridin-3-carboxilamida 169 466,2
139
N-(2,3-dihidrobenzofuran-6-il-metil)-2-[3-(4-fluorofenil)propilsulfanil]piridin-3-carboxilamida 169 423,1
140
2-[3-(4-fluorofenil)propilsulfanil]-N-[[3-(1H-pirazol-1-il)fenil]metil]piridin-3-carboxilamida 169 447,2
141
2-[3-(4-fluorofenil)propilsulfanil]-N-[3-(1H-[1,2,3]triazol-1-il)propil]piridin-3-carboxilamida 169 400,2
142
N-(7-biciclo[2.2.1]heptanilmetil)-2-[3-(4-fluorofenil)propilsulfanil]piridin-3-carboxilamida 169 399,2
144
2-[3-(4-fluorofenil)propilsulfanil]-N-(tiazol-2-ilmetil)piridin-3-carboxilamida 143 388,1
145
2-[3-(4-fluorofenil)propilsulfanil]-N-(tiazol-5-ilmetil)piridin-3-carboxilamida 143 388,1
146
2-[3-(4-fluorofenil)propilsulfanil]-N-(oxazol-2-ilmetil)piridin-3-carboxilamida 143 372,1
148
N-(3,3-dimetilbutil)-2-[3-(4-fluorofenil)propilsulfanil]-4-metilpiridin-3-carboxilamida 147 389,2
149
N-(3,3-dimetilbutil)-2-[[1-metil-3-[3-(trifluorometil)fenil]propil]sulfanil]piridin-3-carboxilamida 115 439,2
150
2-[3-(4-fluorofenil)propilsulfanil]-N-(quinolin-7-ilmetil)piridin-3-carboxilamida 143 432,1
151
2-[3-(4-fluorofenil)propilsulfanil]-N-[(3-piridin-2-ilfenil)metil]piridin-3-carboxilamida 143 458,2
152
2-[3-(4-fluorofenil)propilsulfanil]-N-[(3-piridin-3-ilfenil)metil]piridin-3-carboxilamida 143 458,2
153
N-(3,3-dimetilbutil)-2-[[(1R)-1-metil-3-fenilpropil]sulfanil]piridin-3-carbo ida 115 371,2
154
N-(3,3-dimetilbutil)-2-[[(1S)-1-metil-3-fenilpropil]sulfanil]piridin-3-carboxilamida 115 371,2
155
2-[(2-bencilciclopentil)sulfanil]-N-(3,3-dimetilbutil)piridin-3-carboxilamida 115 397,2
156
N-(7-biciclo[2.2.1]heptanilmetil)-2-[3-[3-(trifluorometil)fenil]propilsulfanil]piridin-3-carboxilamida 169 449,2
157
2-[3-(4-fluorofenil)propilsulfanil]-N-[3-(1H-[1,2,4]triazol-1-il)propil]piridin-3-carboxilamida 143 400,2
158
2-[3-(4-fluorofenil)propilsulfanil]-N-([1,3,4]oxadiazol-2-ilmetil)piridin-3-carboxilamida 143 373,1
159
2-[3-(4-fluorofenil)propilsulfanil]-N-[(3-piridin-4-ilfenil)metil]piridin-3-carboxilamida 143 458,2
160
N-[[4-(ciclopropilmetil)-3,4-dihidro-2H-[1,4]benzoxazin-6-il]metil]-2-[3-(4-fluorofenil)propilsulfanil]piridin-3-carboxilamida 169 492,2
161
N-[(4-etil-3,4-dihidro-2H-[1,4]benzoxazin-6-il)metil]-2-[3-(4-fluorofenil)propilsulfanil]piridin-3-carboxilamida 169 466,2
162
2-[3-(4-fluorofenil)propilsulfanil]-N-[(4-metil-3,4-dihidro-2H-[1,4]benzoxazin-6-il)metil]piridin-3-carboxilamida 169 452,2
163
2-[3-(4-fluorofenil)propilsulfanil]-N-(3-metil-3-fenilbutil)piridin-3-carboxilamida 169 437,2
Ej. decomp.
Designación química Síntesis análogaal ej. de comp. MD m/z[M+H]+
164
N-(7-biciclo[2.2.1]heptanilmetil)-2-[[3,3-difluor-3-(4-fluorofenil)propil]sulfanil]piridin-3-carboxilamida 115 435,2
165
2-[[3,3-difluor-3-[3-(trifluorometil)fenil]propil]sulfanil]-N-[(4-fluorofenil)metil]piridin-3-carboxilamida 115 485,1
166
2-[[3,3-difluor-3-[3-(trifluorometil)fenil]propil]sulfanil]-N-(3,3-dimetilbutil)piridin-3-carboxilamida 169 461,2
168
2-[[3,3-difluor-3-(4-fluorofenil)propil]sulfanil]-N-[(3-fluorofenil)metil]piridin-3-carboxilamida 169 435,1
170
N-butil-2-[[3,3-difluor-3-(4-fluorofenil)propil]sulfanil]piridin-3-carboxilamida 169 383,1
171
2-[[3,3-difluor-3-(4-fluorofenil)propil]sulfanil]-N-(2-metoxietil)piridin-3-carboxilamida 169 385,1
172
2-[3-(4-fluorofenil)propilsulfanil]-N-(2-metoxietil)piridin-3-carboxilamida 169 349,1
173
N-[(4-fluor-2-hidroxifenil)metil]-2-[3-(4-fluorofenil)propilsulfanil]piridin-3-carboxilamida 58 415,1
174
2-[3-(4-fluorofenil)propilsulfanil]-N-(furan-2-ilmetil)piridin-3-carboxilamida 169 371,1
175
2-[3-(4-fluorofenil)propilsulfanil]-N-[(5-metilfuran-2-il)metil]piridin-3-car mida 169 385,1
176
N-[(4-fluorofenil)metil]-2-[[3-(4-fluorofenil)-1-metilpropil]sulfanil]piridin-3-carboxilamida 169 413,1
177
2-[[3-(4-fluorofenil)-1-metilpropil]sulfanil]-N-(3-metilbutil)piridin-3-carboxilamida 169 375,2
178
N-(7-biciclo[2.2.1]heptanilmetil)-2-[[3-(4-fluorofenil)-1-metilpropil]sulfanil]piridin-3-carboxilamida 169 413,2
179
2-[[3,3-difluor-3-(4-fluorofenil)propil]sulfanil]-N-(tetrahidrofuran-2-ilmetil)piridin-3-carboxilamida 169 411,1
180
2-[[3,3-difluor-3-(4-fluorofenil)propil]sulfanil]-N-(tetrahidropiran-2-ilmetil)piridin-3-carboxilamida 169 425,1
181
2-[3-(4-fluorofenil)propilsulfanil]-N-(tetrahidrofuran-2-ilmetil)piridin-3-carboxilamida 169 375,1
182
2-[3-(4-fluorofenil)propilsulfanil]-N-(2-metoxi-3,3-dimetilbutil)piridin-3-carboxilamida 169 405,2
183
2-[[3,3-difluor-3-(4-fluorofenil)propil]sulfanil]-N-(m-tolilmetil)piridin-3-carboxilamida 169 431,1
184
2-[[3,3-difluor-3-(4-fluorofenil)propil]sulfanil]-N-[(3,5-dimetilfenil)metil]piridin-3-carboxilamida 169 445,1
185
2-[[3,3-difluor-3-(4-fluorofenil)propil]sulfanil]-N-propilpiridin-3-carboxilamida 169 369,1
186
2-[[3,3-difluor-3-(4-fluorofenil)propil]sulfanil]-N-hexilpiridin-3-carboxilamida 169 411,2
187
2-[[3,3-difluor-3-(4-fluorofenil)propil]sulfanil]-N-(tetrahidrofuran-3-ilmetil)piridin-3-carboxilamida 169 411,1
188
2-[[3,3-difluor-3-(4-fluorofenil)propil]sulfanil]-N-(tetrahidropiran-3-ilmetil)piridin-3-carboxilamida 169 425,1
189
2-[[3,3-difluor-3-(4-fluorofenil)propil]sulfanil]-N-(tetrahidropiran-4-ilmetil)piridin-3-carboxilamida 169 425,1
190
2-[[3,3-difluor-3-(4-fluorofenil)propil]sulfanil]-N-(furan-2-ilmetil)piridin-3-carboxilamida 169 407,1
191
2-[[3,3-difluor-3-(4-fluorofenil)propil]sulfanil]-N-[(5-metilfuran-2-il)metil]piridin-3-carboxilamida 169 421,1
192
2-[[3,3-difluor-3-(4-fluorofenil)propil]sulfanil]-N-pentilpiridin-3-carboxilamida 169 397,1
193
2-[[3,3-difluor-3-(4-fluorofenil)propil]sulfanil]-N-(3-metoxibutil)piridin-3-carboxilamida 169 413,1
194
2-[[3,3-difluor-3-(4-fluorofenil)propil]sulfanil]-N-(2-metoxipropil)piridin-3-carboxilamida 169 399,1
195
2-[[3,3-difluor-3-(4-fluorofenil)propil]sulfanil]-N-(2-metoxibutil)piridin-3-carboxilamida 169 413,1
196
3-[[2-[[3,3-difluor-3-(4-fluorofenil)propil]sulfanil]piridin-3-carbonil]amino]propanoato de metilo 169 413,1
197
ácido 3-[[2-[[3,3-difluor-3-(4-fluorofenil)propil]sulfanil]piridin-3-carbonil]am no]propiónico 131 399,1
198
2-[[3,3-difluor-3-(4-fluorofenil)propil]sulfanil]-N-(2-dimetilaminoetil)piridin-3-carboxilamida 169 398,1
199
2-[[3-(3,4-difluorofenil)-1-metilpropil]sulfanil]-N-[(4-fluorofenil)metil]piridin-3-carboxilamida 169 431,1
200
2-[[3-(3,4-difluorofenil)-1-metilpropil]sulfanil]-N-(3-metilbutil)piridin-3-carboxilamida 169 393,2
201
N-[(4-fluorofenil)metil]-2-[[3-(3-fluorofenil)-1-metilpropil]sulfanil]piridin-3-carboxilamida 169 413,1
imagen36
imagen37
imagen38
imagen39
imagen40
imagen41
imagen42

Claims (1)

  1. imagen1
    imagen2
    imagen3
    imagen4
    imagen5
    imagen6
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    imagen8
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TWI504395B (zh) * 2009-03-10 2015-10-21 Substituted 3-amino-2-mercaptoquinoline as a KCNQ2 / 3 modifier
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TWI461197B (zh) 2009-03-12 2014-11-21 2-mercaptoquinoline-3-carboxamide as a KCNQ2 / 3 modifier
PL2609086T3 (pl) 2010-08-27 2015-07-31 Gruenenthal Gmbh Podstawione 2-okso- i 2-tiookso-dihydrochinolino-3-karboksyamidy jako modulatory KCNQ2/3
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KR20130100300A (ko) 2010-08-27 2013-09-10 그뤼넨탈 게엠베하 Ｋｃｎｑ２／３ 조절제로서의 치환된 ２-옥시-퀴놀린-３-카복스아미드
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