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ES2484371T3 - 2-mercapto-3-aminopiridinas sustituidas como moduladores de kcnq2/3 - Google Patents

2-mercapto-3-aminopiridinas sustituidas como moduladores de kcnq2/3 Download PDF

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ES2484371T3
ES2484371T3 ES10708140.8T ES10708140T ES2484371T3 ES 2484371 T3 ES2484371 T3 ES 2484371T3 ES 10708140 T ES10708140 T ES 10708140T ES 2484371 T3 ES2484371 T3 ES 2484371T3
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alkyl
heteroaryl
aryl
substituted
heterocyclyl
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Sven KÜHNERT
Beatrix Merla
Achim Kless
Gregor Bahrenberg
Wolfgang Schröder
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    • 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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    • 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
    • C07D213/60—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 with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

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Abstract

2-mercapto-3-aminopiridinas sustituidas de fórmula general (1), donde R1 representa alquilo(C1-6), saturado o insaturado, lineal o ramificado, no sustituido o sustituido de forma simple o múltiple; cicloalquilo(C3-10) o heterociclilo, en cada caso saturado o insaturado, no sustituido o sustituido de forma simple o múltiple; arilo o heteroarilo, en cada caso no sustituido o sustituido de forma simple o múltiple; con la condición de que, cuando R1 represente heterociclilo, la unión del heterociclilo con la estructura general superior tenga lugar a través de un átomo de carbono del heterociclilo; R2 representa arilo o heteroarilo, en cada caso no sustituido o sustituido de forma simple o múltiple; Y se selecciona de entre el grupo consistente en -(CR9aR9b)-, S(>=O)2, S(>=O), -S-, -O-, C(>=O); R3, R4, R5, R6a, R6b, R7a, R7b, R8a, R8b, R9a y R9b representan en cada caso, independientemente entre sí, H; F; Cl; Br; I; NO2; CF3; CN; OH; OCF3; SH; SCF3; NH2; alquilo(C1-6), O-alquilo(C1-6), OC(>= O)-alquilo(C1-6), S-alquilo(C1-6), NH(alquilo(C1-6)), N(alquilo(C1-6))2, NH-C(>=O)-alquilo(C1-6), N(C(>=O)-alquilo(C1-6))2 o C(>=O)-alquilo(C1-6), en cada caso saturado o insaturado, lineal o ramificado, no sustituido o sustituido de forma simple o múltiple; cicloalquilo(C3-7) o heterociclilo, en cada caso saturado o insaturado, ramificado o no ramificado, no sustituido o sustituido de forma simple o múltiple; pudiendo formar R7a con R8a un grupo cicloalquilo(C3-7), que puede ser saturado o insaturado, no sustituido o sustituido de forma simple o múltiple; donde la expresión "sustituido con alquilo" significa la sustitución de uno o más átomos de hidrógeno, en cada caso independientemente entre sí, por F; Cl; Br; I; NO2; CF3; CN; alquilo(C1-8); heteroalquilo(C2-8); arilo; heteroarilo; cicloalquilo(C3-10); heterociclilo; arilo, heteroarilo, cicloalquilo(C3- 10) o heterociclilo unido a través de un alquilo(C1-8) o un heteralquilo(C2-8); CHO; C(>=O)alquilo(C1-8); C(>=O)arilo; C(>=O)heteroarilo; CO2H; C(>=O)O-alquilo(C1-8); C(>=O)O-arilo; C(>=O)O-heteroarilo; CONH2; C(>=O)NH-alquilo(C1-8); C(>=O)N(alquilo(C1-8))2; C(>=O)NH-arilo; C(>=O)N(arilo)2; C(>=O)NHheteroarilo; C(>=O)N(heteroarilo)2; C(>=O)N(alquil(C1-8))(arilo); C(>=O)N(alquil(C1-8))(heteroarilo); C(>=O)N(heteroaril)(arilo); OH; O-alquilo(C1-8); OCF3; O-(alquilo(C1-8))-OH; O-(alquil(C1-8))-Oalquilo( C1-8); O-bencilo; O-arilo; O-heteroarilo; O-C(>=O)alquilo(C1-8); O-C(>=O)arilo; OC(>= O)heteroarilo; NH2; NH-alquilo(C1-8); N(alquilo(C1-8))2; NH-C(>=O)alquilo(C1-8); N(alquil(C1-8))- C(>=O)alquilo(C1-8); N(C(>=O)alquilo(C1-8))2; NH-C(>=O)-arilo; NH-C(>=O)-heteroarilo; SH; S-alquilo(C1-8); SCF3; S-bencilo; S-arilo; S-heteroarilo; S(>=O)2alquilo(C1-8); S(>=O)2arilo; S(>=O)2heteroarilo; S(>=O)2OH; S(>=O)2O-alquilo(C1-8); S(>=O)2O-arilo; S(>=O)2O-heteroarilo; S(>=O)2-NH-alquilo(C1-8); S(>=O)2-NH-arilo; y S(>=O)2-NH-heteroarilo(C1-8).

Description

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Ej.
Designación química Prep. Análg.al ejemplo Rdto. [%] MS m/z [M+H]+
49
2-cicloheptil-N-[2-[2-[[3-(trifluorometil)fenil]sulfonil]etilsulfanil]piridin-3-il]acetamida 14 64 501,1
52
2-(1,2,3,4-tetrahidro-naftalen-2-il)-N-[2-[2-[[3-(trifluorometil)fenil]sulfonil]etilsulfanil]-piridin-3-il]acetamida 14 58 535,1
53
2-hidroxi-N-[2-[2-[[3-(trifluorometil)fenil]sulfonil]etilsulfanil]piridin-3-il]benzamida 14 31 483,1
56
N-[4-metil-2-[2-[[3-(trifluorometil)fenil]sulfonil]etilsulfanil]piridin-3-il]-2-tiofen-2-ilacetamida 1 49 501,1
57
3-(1,2,3,4-tetrahidronaftalen-2-il)-N-[2-[2-[[3-(trifluorometil)fenil]sulfonil]etilsulfanil]-piridin-3-il]propionamida 14 52 549,1
58
3-cicloheptil-N-[2-[2-[[3-(trifluorometil)fenil]sulfonil]etilsulfanil]piridin-3-il]propionamida 14 47 515,2
59
2-(benzo[b]tiofen-2-il)-N-[2-[2-[[3-(trifluorometil)fenil]sulfonil]etilsulfanil]piridin-3-il]-acetamida 14 54 537,1
61
N-[2-[2-[(4-fluorofenil)sulfanil]etilsulfanil]piridin-3-il]-3,3-dimetilbutiramida 1 74 379,1
62
2-(5-biciclo[2.2.1]heptanil)-N-[2-[2-[[3-(trifluorometil)fenil]sulfonil]etilsulfanil]piridin-3-il]-acetamida 14 55 499,1
63
N-[2-[2-(4-fluorofenoxi)etilsulfanil]piridin-3-il]-3,3-dimetilbutiramida 1 35 363,1
64
3,4-diflúor-N-[2-[2-(4-fluorofenoxi)etilsulfanil]piridin-3-il]benzamida 1 55 405,1
65
3,4-diflúor-N-[2-[3-(4-fluorofenil)propilsulfanil]piridin-3-il]benzamida 1 60 403,1
66
N-[2-[3-(4-fluorofenil)propilsulfanil]piridin-3-il]-3,3-dimetilbutiramida 1 48 361,2
67
2-cicloheptil-N-[2-[2-[(4-fluorofenil)sulfonil]etilsulfanil]piridin-3-il]acetamida 14 18 451,1
68
2-ciclohexil-2,2-diflúor-N-[2-[2-[[3-(trifluorometil)fenil]sulfonil]etilsulfanil]piridin-3-il]-acetamida 55 11 523,1
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Ej. nº
% de eficacia de fluorimetría (I/EC50, retigabina = 100%) Fluorimetría EC50 [nM] Fluorimetría IC50 [nM] Ensayo de formalina en ratón IV efecto @ dosis [mg/kg]
11
109 588
12
141 168
13
46
14
167 45
18
43 457
19
-43
20
97 180
21
152 83
22
155 732
23
165 157
24
84 153
25
170 71
26
82 123
27
112 208
28
152 277
29
108 312
31
109 841
33
106 141
35
43
36
38
37
31
38
35
39
139 363
40
52
41
127 99
44
80 153
45
58
46
50
47
95 265
48
93 174
49
108 19
50
51
32 106
52
59 208
53
27,45
55
84,85 3600
56
98,1 348,5
57
134 56,5
58
167,4 47,5
59
138,55 925
60
101 1025
61
128,55 27,5
62
168,4 23,5
63
119 546
64
49 200
65
148 480
66
176 184
67
114 18
68
79 22

Claims (1)

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ES10708140.8T 2009-03-12 2010-03-11 2-mercapto-3-aminopiridinas sustituidas como moduladores de kcnq2/3 Active ES2484371T3 (es)

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EP09003604 2009-03-12
EP09003604 2009-03-12
PCT/EP2010/001508 WO2010102810A1 (de) 2009-03-12 2010-03-11 Substituierte 2-mercapto-3-aminopyridine als kcnq2/3 modulatoren

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US (1) US8247573B2 (es)
EP (1) EP2406224B1 (es)
JP (1) JP5583148B2 (es)
KR (1) KR20110126751A (es)
CN (1) CN102341373A (es)
AR (1) AR078027A1 (es)
AU (1) AU2010223512B2 (es)
BR (1) BRPI1008963A2 (es)
CA (1) CA2755002A1 (es)
CO (1) CO6410290A2 (es)
EC (1) ECSP11011345A (es)
ES (1) ES2484371T3 (es)
IL (1) IL214947A0 (es)
MX (1) MX2011008662A (es)
NZ (1) NZ595627A (es)
PE (1) PE20120667A1 (es)
RU (1) RU2011141189A (es)
TW (1) TW201038565A (es)
WO (1) WO2010102810A1 (es)
ZA (1) ZA201107443B (es)

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Publication number Priority date Publication date Assignee Title
TWI504395B (zh) * 2009-03-10 2015-10-21 Substituted 3-amino-2-mercaptoquinoline as a KCNQ2 / 3 modifier
WO2010102778A2 (de) * 2009-03-10 2010-09-16 Grünenthal GmbH Substituierte 3-aminoisoxazolopyridine als kcnq2/3 modulatoren
TWI461197B (zh) * 2009-03-12 2014-11-21 2-mercaptoquinoline-3-carboxamide as a KCNQ2 / 3 modifier
TWI475020B (zh) 2009-03-12 2015-03-01 The substituted nicotine amide as a KCNQ2 / 3 modifier
AR082733A1 (es) 2010-08-27 2012-12-26 Gruenenthal Gmbh 2-amino-quinolina-3-carboxamidas sustituidas como moduladores de kcnq2/3
PE20140214A1 (es) 2010-08-27 2014-02-19 Gruenenthal Chemie 2-oxo- y 2-tioxo-dihidroquinolina-3-carboxamidas sustituidos como moduladores kcnq2/3
BR112013004562A2 (pt) 2010-08-27 2016-09-06 Gruenenthal Gmbh 2-óxi-quinolina-3-carboxamidas substituídas como moduladores kcnq2/3
AU2011297937B2 (en) 2010-09-01 2015-10-01 Grunenthal Gmbh Substituted 1-oxo-dihydroisoquinoline-3-carboxamides as KCNQ2/3 modulators
NZ610689A (en) * 2010-10-20 2014-08-29 Gruenenthal Chemie Substituted 6-amino-nicotinamides as kcnq2/3 modulators

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AU2010223512A1 (en) 2011-11-03
IL214947A0 (en) 2011-11-30
WO2010102810A1 (de) 2010-09-16
EP2406224B1 (de) 2014-04-23
JP2012520248A (ja) 2012-09-06
AU2010223512B2 (en) 2015-01-22
PE20120667A1 (es) 2012-06-01
RU2011141189A (ru) 2013-04-20
US20100234428A1 (en) 2010-09-16
ZA201107443B (en) 2012-07-25
AR078027A1 (es) 2011-10-12
EP2406224A1 (de) 2012-01-18
ECSP11011345A (es) 2011-10-31
MX2011008662A (es) 2011-09-06
CA2755002A1 (en) 2010-09-16
TW201038565A (en) 2010-11-01
US8247573B2 (en) 2012-08-21
BRPI1008963A2 (pt) 2016-03-15
NZ595627A (en) 2012-10-26
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CN102341373A (zh) 2012-02-01
KR20110126751A (ko) 2011-11-23

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