ES2556460T3 - Derivados novedosos de metilciclohexano y usos de los mismos - Google Patents
Derivados novedosos de metilciclohexano y usos de los mismos Download PDFInfo
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- ES2556460T3 ES2556460T3 ES11829552.6T ES11829552T ES2556460T3 ES 2556460 T3 ES2556460 T3 ES 2556460T3 ES 11829552 T ES11829552 T ES 11829552T ES 2556460 T3 ES2556460 T3 ES 2556460T3
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- pyridin
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Abstract
Un compuesto seleccionado del grupo que consiste en un derivado de metilciclohexano representado por la Fórmula I siguiente y una sal, un solvato y un hidrato del derivado de metilciclohexano farmacéuticamente aceptables y una combinación de los mismos.**Fórmula** en la que Ar se selecciona entre el grupo que consiste en fenilo, piridina y piridin-N-óxido, cada uno de los cuales está sustituido con uno o más sustituyentes idénticos o diferentes seleccionados del grupo que consiste en un átomo de hidrógeno, un alquilo C1 a C6 lineal o ramificado, halógeno, un alcoxi C1 a C6 lineal o ramificado y trifluorometilo; X es O, (C>=O)O, NR1(C>=O)O, NH, (C>=O)NH o O(C>=O)NH y R1 es H o CH3; Y es CH2, O o N-R2; R2 es H o CH3; A es O o NH; B es CH o N; y m es un número entero entre 0 y 2 y n es 0 o 1.
Description
(m, 3H), 3,91 (s, 2H), 3,40~3,23 (m, 4H), 3,01~2,91 (m, 3H), 2,11~1,51 (m, 9H), 1,42~1,05 (m, 4H)
Ejemplo 11: Síntesis del éster 4-(1-oxi-piridin-4-ilmetilcarbamoiloxi)-ciclohexilmetílico del ácido pirrolidin-1carboxílico
Un compuesto objetivo (393 mg, 52 % de rendimiento) se obtuvo de la misma manera que en el Ejemplo 1, excepto que se utilizó como material de partida C-(1-oxi-piridin-4-il)metilamina.
10 RMN de 1H (500 MHz, CDCl3), ppm (δ): 8,14-8,13 (d, 2H, J = 6,3 Hz), 7,29-7,21 (d, 2H, J = 6,3 Hz), 5,95 (s, 1H), 4,58-4,52 (m, 1H) , 3,91-3,85 (m, 2H), 3,36-3,30 (m, 5H), 3,00-2,50 (m, 1H), 2,0 (m, 2H), 1,83-1,82 (m, 7H), 1,591,53 (m, 2H), 1,31-1,21 (m, 4H), 1,14-1,3 (m, 2H)
15 Ejemplo 12: Síntesis del éster 4-(1-oxi-piridin-3-ilmetilcarbamoiloxi)-ciclohexilmetílico del ácido pirrolidin-1carboxílico
20 Un compuesto objetivo (325 mg, 43 % de rendimiento) se obtuvo de la misma manera que en el Ejemplo 1, excepto que se utilizó como material de partida C-(1-oxi-piridin-3-il)-metilamina.
RMN de 1H (500 MHz, CDCl3), ppm (δ): 8,21-8,13 (m, 1H), 7,26-7,24 (m, 3H), 5,16-4,59 (m, 1H), 4,35 (m, 1H), 3,923,91 (m, 1H), 3,41-3,33 (m, 2H), 2,8-2,4 (m, 1H), 1,87-1,84 (m, 4H), 1,63 (m, 4H), 1,35-1,11 (m, 2H)
25 Ejemplo 13: Síntesis del éster 4-(1-oxi-piridin-2-ilmetilcarbamoiloxi)-ciclohexilmetílico del ácido pirrolidin-1carboxílico
Un compuesto objetivo (264 mg, 35 % de rendimiento) se obtuvo de la misma manera que en el Ejemplo 1, excepto que se utilizó como material de partida C-(1-oxi-piridin-2-il)metilamina.
14
RMN de 1H (500 MHz, CDCl3), ppm (δ): 8,29-8,19 (d, 1H, J = 6,3 Hz), 7,38-7,37 (m, 1H), 7,25-7,18 (m, 2H), 6,236,21 (m, 1H), 4,48-4,45 (m, 3H), 3,85-3,82 (m, 2H), 3,32-3,25 (m, 4H), 1,97-1,93 (m, 2H), 1,81-1,74 (m, 6H), 1,581,82 (m , 2H), 1,27-1,20 (m, 4H)
Ejemplo 14: Síntesis del éster 4-(6-cloro-piridin-2-ilmetilcarbamoiloxi)-ciclohexilmetílico del ácido pirrolidin1-carboxílico
10 Un compuesto objetivo (491 mg, 62 % de rendimiento) se obtuvo de la misma manera que en el Ejemplo 1, excepto que se utilizó como material de partida C-(6-cloro-piridin-2-il)metilamina.
RMN de 1H (300 MHz, CDCl3), ppm (δ): 7,67~7,60 (m, 1H), 7,26~7,21 (m, 2H), 5,61~5,55 (m, 1H), 4,64~4,53 (m, 1H), 4,44 (d, 2H, J = 5,7 Hz), 3,90 (d, 2H, J = 6,0 Hz), 3,42~3,28 (m, 4H), 2,10~1,99 (m, 2H), 1,92~1,84 (m, 5H), 15 1,67~1,55 (m, 2H), 1,40~1,03 (m, 4H)
Ejemplo 15: Síntesis del éster 4-(6-metil-piridin-2-ilmetilcarbamoiloxi)-ciclohexilmetílico del ácido pirrolidin-1ácido carboxílico
Un compuesto objetivo (451 mg, 60 % de rendimiento) se obtuvo de la misma manera que en el Ejemplo 1, excepto que se utilizó como material de partida C-(6-metil-piridin-2-il)metilamina.
25 RMN de 1H (300 MHz, CDCl3), ppm (δ): 7,58~7,50 (m, 1H), 7,10~7,01 (m, 2H), 5,84~5,79 (m, 1H), 4,65~4,55 (m, 1H), 4,44 (d, 2H, J = 5,1 Hz), 3,90 (d, 2H, J = 6,3 Hz), 3,42~3,10 (m, 4H), 2,53 (s, 3H), 2,15~1,99 (m, 2H), 1,95~1,75 (m, 5H), 1,73~1,52 (m, 2H), 1,44~1,03 (m, 4H)
Ejemplo 16: Síntesis del éster 4-(2-cloro-piridin-4-ilmetilcarbamoiloxi)-ciclohexilmetílico del ácido pirrolidin30 1-carboxílico
Un compuesto objetivo (523 mg, 66 % de rendimiento) se obtuvo de la misma manera que en el Ejemplo 1, excepto que se utilizó como material de partida C-(2-cloro-piridin-4-il)metilamina.
15
RMN de 1H (300 MHz, CDCl3), ppm (δ): 8,33 (d, 1H, J = 5,1 Hz), 7,25 (s, 1H), 7,14 (d, 1H, J = 4,8 Hz), 5,33~5,26 (m, 1H), 4,65~4,54 (m, 1H), 4,36 (d, 2H, J = 6,3 Hz), 3,90 (d, 2H, J = 6,3 Hz), 3,41~3,29 (m, 4H), 2,18~1,99 (m, 2H), 1,95~1,77 (m, 6H), 1,70~1,52 (m, 1H), 1,43~1,03 (m, 4H)
Ejemplo 17: Síntesis del éster 4-(6-cloro-piridin-3-ilmetilcarbamoiloxi)-ciclohexilmetílico del ácido pirrolidin1-carboxílico
10 Un compuesto objetivo (435 mg, 55 % de rendimiento) se obtuvo de la misma manera que en el Ejemplo 1, excepto que se utilizó como material de partida C-(6-cloro-piridin-3-il)-metilamina.
RMN de 1H (300 MHz, CDCl3), ppm (~): 8,31 (s, 1H), 7,63 (d, 1H, J = 7,2 Hz), 7,30 (d, 1H, J = 8,4 Hz), 5,20~5,12 (m, 1H), 4,63~4,52 (m, 1H), 4,34 (d, 2H, J = 6,0 Hz), 3,90 (d, 2H, J = 6,6 Hz), 3,41~3,28 (m, 4H), 2,13~1,99 (m, 2H), 15 1,97~1,72 (m, 6H), 1,69~1,53 (m, 1H), 1,42~1,04 (m, 4H)
Ejemplo 18: Síntesis del éster 4-(2-cloro-piridin-3-ilmetilcarbamoiloxi)-ciclohexilmetílico del ácido pirrolidin1-carboxílico
Un compuesto objetivo (404 mg, 51 % de rendimiento) se obtuvo de la misma manera que en el Ejemplo 1, excepto que se utilizó como material de partida C-(2-cloro-piridin-3-il)-metilamina.
25 RMN de 1H (300 MHz, CDCl3), ppm (δ): 8,34~8,28 (m, 1H), 7,75 (d, 1H, J = 6,6 Hz), 7,27~7,21 (m, 1H), 5,35~5,27 (m, 1H), 4,62~4,50 ( m, 1H), 4,42 (d, 2H, J = 6,6 Hz), 3,90 (d, 2H, J = 6,3 Hz), 3,42~3,28 (m, 4H), 2,15~1,77 (m, 8H), 1,74~1,50 (m, 1H), 1,46~1,02 (m, 4H)
Ejemplo 19: Síntesis del éster del 4-(6-trifluorometil-piridin-3-ilmetilcarbamoiloxi)-ciclohexilmetílico del ácido 30 pirrolidin-1-carboxílico
16
Ejemplo 29: Síntesis del éster 4-bencilcarbamoiloxi-ciclohexilmetílico del ácido 4-metil-piperazin-1carboxílico
5 Un compuesto objetivo (101 mg, 13 % de rendimiento) se obtuvo de la misma manera que en el Ejemplo 1, excepto que fueron utilizados como materiales de partida bencilamina y 1-metil-piperazina y el yoduro de metilo no se utilizó en el segundo paso.
10 RMN de 1H (500 MHz, CDCl3), ppm (δ): 7,38~7,24 (m, 5H), 4,96 (sa, 1H), 4,65~4,54 (m, 1H), 3,92 (d, 2H, J = 6,4 Hz), 3,51~3,47 (m, 4H), 2,41~2,34 (m, 4H), 2,30 (s, 3H), 2,12~2,02 (m, 1H), 1,94~1,79 (m, 2H), 1,68~1,52 (m, 2H), 1,38~1,29 ( m, 2H), 1,20~1,09 (m, 2H)
15
A una solución de éster 4-hidroxi-ciclohexilmetílico del ácido pirrolidin-1-carboxílico (1 mmol) en cloruro de metileno (5 ml) se añadieron cloruro de picolinoílo (1,1 mmol) y trietilamina (1,5 mmol) y la mezcla resultante se agitó durante
20 16 horas a temperatura ambiente. La mezcla de reacción se diluyó con agua, seguido de par de veces de extracción con cloruro de metileno. La capa orgánica combinada se secó sobre sulfato de magnesio anhidro, se filtró y se concentró a presión reducida. El residuo se purificó por cromatografía en columna (gel de sílice, acetato de etilo), completando de este modo la preparación de un compuesto objetivo (233 mg, rendimiento del 70 %).
25 RMN del 1H (300 MHz, CDCl3), ppm (δ): 8,80~8,76 (m, 1H), 8,15~8,11 (m, 1H), 7,90~7,80 (m, 1H), 7,50~7,45 (m, 1H), 5,08~4,98 (m, 1H ), 3,98 (d, 2H, J = 6,6 Hz), 3,43~3,33 (m, 4H), 2,17~2,08 (m, 2H), 1,99~1,83 (m, 5H), 1,81~1,53 (m, 3H), 1,20~1,08 (m, 3H)
Los Ejemplos 31 a 33 siguientes se llevan a cabo cada uno de la misma manera que en el Ejemplo 30, excepto que 30 el material de partida utilizado era diferente del material de partida utilizado en el Ejemplo 30.
20
- Ejemplo 13
- 27,9 >50
- Ejemplo 14
- 21,7 22,3
- Ejemplo 15
- 19,9 19,4
- Ejemplo 16
- 27,9 10,8
- Ejemplo 17
- 29,5 12,5
- Ejemplo 18
- 5,7 18,3
- Ejemplo 19
- 11,1 13,8
- Ejemplo 20
- 50 37,9
- Ejemplo 21
- 15,9 44,8
- Ejemplo 22
- 35,8 21,7
- Ejemplo 23
- 28,6 >50
- Ejemplo 24
- >50 >50
- Ejemplo 25
- 24,9 15,5
- Ejemplo 26
- 46,1 36,8
- Ejemplo 27
- 50,0 >50
- Ejemplo 28
- >50 44,8
- Ejemplo 29
- 46,1 >50
- Ejemplo 30
- >50 >50
- Ejemplo 31
- >50 21,1
- Ejemplo 32
- 21,1 34,8
- Ejemplo 33
- >50 >50
- Ejemplo 34
- 24,9 27,1
- Ejemplo 35
- >50 50,0
- Ejemplo 36
- >50 >50
- Ejemplo 37
- 46,1 >50
- Ejemplo 38
- 35,8 >50
- Ejemplo 39
- >50 >50
- Ejemplo 40
- >50 >50
- Ejemplo 41
- 50 >50
- Ejemplo 42
- 50 >50
- Ejemplo 43
- 10,5 12,0
- Ejemplo 44
- 21,7 16,8
- Ejemplo 45
- 9,9 7,5
- Ejemplo 46
- 32,0 26,3
- Ejemplo 47
- 13,1 21,1
- Ejemplo 48
- 13,5 10,2
- Ejemplo 49
- 12,0 10,2
- Ejemplo 50
- 5,7 14,2
- Ejemplo 51
- 50 >50
- Ejemplo 52
- 22,3 >50
- Ejemplo 53
- 33,9 >50
- Ejemplo 54
- 48,7 >50
- Ejemplo 55
- 25,6 >50
Ejemplo 57: Prueba de alivio del dolor utilizando un modelo animal
1) Modelo animal 5 Se adquirieron as ratas macho (Sprague-Dawley, 150-200 g, de 6 semanas de edad, Orient Bio Co., Ltd) y se aclimataron en una cámara de animales durante una semana. La cámara de animales se encendía y apagaba alternativamente a intervalos de 12 horas, con una temperatura de 22 a 25 ºC y una humedad relativa de 40-60 % y se suministró agua y alimento ad libitum a las ratas. 10
31
Claims (1)
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PCT/KR2011/007117 WO2012044046A2 (en) | 2010-09-29 | 2011-09-28 | Novel methylcyclohexane derivatives and uses thereof |
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EP (1) | EP2621899B1 (es) |
JP (1) | JP5921555B2 (es) |
KR (1) | KR101803955B1 (es) |
CN (1) | CN103237790B (es) |
AU (1) | AU2011308174A1 (es) |
BR (1) | BR112013005873A2 (es) |
CA (1) | CA2813189C (es) |
CL (1) | CL2013000835A1 (es) |
ES (1) | ES2556460T3 (es) |
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GB0030710D0 (en) * | 2000-12-15 | 2001-01-31 | Hoffmann La Roche | Piperazine derivatives |
US6802897B1 (en) * | 2002-05-31 | 2004-10-12 | Marathon Ashland Petroleum Llc | Biodiesel sulfur slurry |
FR2842885B1 (fr) * | 2002-07-24 | 2004-09-10 | Inst Francais Du Petrole | Procede de transport des petroles bruts lourds sous forme de dispersion |
EP1660058A2 (en) | 2003-07-28 | 2006-05-31 | Merz Pharma GmbH & Co. KGaA | The use of 1-amino-alkylcyclohexane compounds in the treatment of pain hypersensitivity |
US20060063930A1 (en) | 2004-08-20 | 2006-03-23 | Agoston Gregory E | Compositions and methods comprising proteinase activated receptor antagonists |
FR2878937B1 (fr) * | 2004-12-07 | 2007-02-09 | Inst Francais Du Petrole | Methode de traitement d'un hydrocarbure visqueux par inertage in situ des asphaltenes |
TWI466879B (zh) * | 2005-04-13 | 2015-01-01 | Neuraxon Inc | 具有一氧化氮合成酶抑制活性之取代的吲哚化合物 |
TW200938203A (en) | 2007-12-17 | 2009-09-16 | Intervet Int Bv | Anthelmintic agents and their use |
BRPI0907248A2 (pt) | 2008-01-09 | 2019-02-26 | Pgxhealth, Llc | tratamento intratecal de dor neuropática com agonistas a2ar |
US20090298834A1 (en) * | 2008-06-02 | 2009-12-03 | Hassan Pajouhesh | 4-(aminomethyl)cyclohexanamine derivatives as calcium channel blockers |
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CA2813189A1 (en) | 2012-04-05 |
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CL2013000835A1 (es) | 2013-10-18 |
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