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ES2551898T3 - Derivado de benceno o tiofeno y su uso como inhibidor de la enzima VAP-1 - Google Patents

Derivado de benceno o tiofeno y su uso como inhibidor de la enzima VAP-1 Download PDF

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Publication number
ES2551898T3
ES2551898T3 ES09754868.9T ES09754868T ES2551898T3 ES 2551898 T3 ES2551898 T3 ES 2551898T3 ES 09754868 T ES09754868 T ES 09754868T ES 2551898 T3 ES2551898 T3 ES 2551898T3
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ES
Spain
Prior art keywords
mmol
butyl
vap
acetyl
mixture
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ES09754868.9T
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Inventor
Tatsuya Matsukawa
Kazuhiro Masuzaki
Akiko Kawasaki
Akiko Akasaka
Yosuke Kawai
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R Tech Ueno Ltd
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R Tech Ueno Ltd
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
    • A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
    • C07C243/26—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C243/28—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of a saturated carbon skeleton
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    • A61K31/4025—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil not condensed and containing further heterocyclic rings, e.g. cromakalim
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Abstract

Un compuesto, el cual es 2-(4-{2-[5-(4-acetilpiperazin-1-il)piridin-2-il]etil}fenil)acetohidrazida, o una de sus sales farmacéuticamente aceptables.

Description

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E09754868
30-10-2015
Etapa 2
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Se añadió etiniltrimetilsilano (6,3 mL, 45,5 mmol) a una disolución de 2-[(4-bromofenil)acetil]hidrazinacarboxilato de terc-butilo (10 g, 30,4 mmol), yoduro de cobre (I) (579 mg, 3,04 mmol), diclorobis(trifenilfosfina)paladio (II) (2,13 g,
5 3,03 mmol) y trietilamina (8,5 mL, 61,0 mmol) en N,N-dimetilformamida anhidra (50 mL). Después de agitar toda la noche at 50°C, se añadió agua a la mezcla de reacción, y la mezcla se extrajo con acetato de etilo y se concentró a presión reducida. El residuo concentrado se purificó por cromatografía en columna de gel de sílice (acetato de etilo:hexano = 30:70 → 35:65) para dar 2-({4-[(trimetilsilil)etinil]fenil}acetil)hidrazinacarboxilato de terc-butilo (7,1 g, rendimiento 68%) como un sólido marrón verdoso.
10 Etapa 3
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A una disolución de 2-({4-[(trimetilsilil)etinil]fenil}acetil)hidrazinacarboxilato de terc-butilo (10,1 g, 29,4 mmol) en tetrahidrofurano anhidro (150 mL) se añadió a 0°C fluoruro de tetra-n-butilamonio (disolución 1M en tetrahidrofurano, 29,4 mL, 29,4 mmol). Después de agitar a 0°C durante 45 min, la mezcla se concentró a presión reducida. Se añadió
15 agua al residuo y la mezcla se extrajo con acetato de etilo, y el extracto se concentró a presión reducida. El residuo concentrado se purificó por cromatografía en columna de gel de sílice (acetato de etilo:hexano = 1:1) para dar 2-[(4etinilfenil)acetil]hidrazinacarboxilato de terc-butilo (7,7 g, rendimiento 96%) como un sólido amarillo.
1H-RMN (DMSO-d6)  (ppm): 9,80 (brs, 1H), 8,75 (brs, 1H), 7,42 (d, J = 8,2 Hz, 2H), 7,29 (d, J = 8,2 Hz, 2H), 4,13 (s, 1H), 3,44 (s, 2H), 1,45-1,20 (brs, 9H).
20 Etapa 4
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Se añadieron acetato de paladio (II) (2,5 mg, 0,011 mmol) y trifenilfosfina (11 mg, 0,044 mmol) a diisopropilamina (4 mL), y la mezcla se agitó a temperatura ambiente durante 20 min. Se añadieron N-(4-bromofenil)acetamida (78 mg, 0,365 mmol) y 2-[(4-etinilfenil)acetil]hidrazinacarboxilato de terc-butilo (100 mg, 0,365 mmol), y la mezcla se agitó a
25 70°C durante 2 h. Se añadió acetonitrilo anhidro (2 mL), y la mezcla se agitó adicionalmente a 70°C durante 1 h. La mezcla de reacción se enfrió y se concentró. El residuo se purificó por cromatografía en columna de gel de sílice (diclorometano:metanol = 97:3) para dar 2-({4-[(4-acetamidofenil)etinil]fenil}acetil)hidrazinacarboxilato de terc-butilo (30 mg, rendimiento 20%).
Etapa 5
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E09754868
30-10-2015
Se disolvió 2-({4-[(4-acetamidofenil)etinil]fenil}acetil)hidrazinacarboxilato de terc-butilo (29 mg, 0,071 mmol) en una mezcla de tetrahidrofurano-metanol (1:1) y se hidrogenó usando un reactor de hidrogenación en continuo (nombre comercial: H-CUBE, fabricado por ThalesNano) equipado con un cartucho de paladio al 10%-carbono. La mezcla de reacción se concentró, y el residuo se purificó por cromatografía en columna de gel de sílice (diclorometano:metanol = 97:3) para dar 2-({4-[(4-acetamidofenil)etil]fenil}acetil)hidrazinacarboxilato de terc-butilo (24 mg, rendimiento 82%).
Etapa 6
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Se añadió una disolución de cloruro de hidrógeno 4M en dioxano (1 mL, 4 mmol) a 2-({4-[(4acetamidofenil)etil]fenil}acetil)hidrazinacarboxilato de terc-butilo (23 mg, 0,056 mmol), y la mezcla se agitó a temperatura ambiente durante 15 min. La mezcla de reacción se concentró a presión reducida, se añadió diclorometano, y la mezcla se concentró otra vez, y se separó el gas cloruro de hidrógeno. El precipitado se recogió por filtración, se lavó con éter dietílico y se secó a presión reducida para dar el compuesto del título (18 mg, rendimiento 98%) como un sólido ligeramente amarillo.
Ejemplo de producción 86 (Referencia)
Tetrahidrocloruro de 2-{4-[2-(5-piperazin-1-ilpiridin-2-il)etil]fenil}acetohidrazida
Etapa 1
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A una disolución de 3-piperazin-4-ilpiridina (2,0 g, 12,25 mmol) en diclorometano (20 mL) se añadió una disolución de dicarbonato de di-terc-butilo (3,21 g, 14,7 mmol) en diclorometano (5 mL) a temperatura ambiente, y la mezcla se agitó durante 1 h. La mezcla de reacción se diluyó con diclorometano, se lavó con salmuera saturada, se secó sobre sulfato de sodio anhidro, y se concentró para dar 4-piridin-3-ilpiperazina-1-carboxilato de terc-butilo (3,20 g, rendimiento 99%) como un aceite ligeramente amarillo.
Etapa 2
imagen14
A una disolución de 4-piridin-3-ilpiperazina-1-carboxilato de terc-butilo (1,0 g, 3,80 mmol) en acetonitrilo (12 mL) se añadió N-bromosuccinimida (676 mg, 3,80 mmol) en pequeñas porciones a temperatura ambiente. Después de agitar a temperatura ambiente durante 1,5 h, la mezcla de reacción se vertió en una mezcla de disolución acuosa de hidróxido de sodio 1M y acetato de etilo. La mezcla se agitó, se dejó reposar y se repartió. La capa orgánica se lavó con salmuera saturada, se secó sobre sulfato de sodio anhidro, y se concentró a presión reducida para dar 4-(6bromopiridin-3-il)piperazina-1-carboxilato de terc-butilo (1,26 g, rendimiento 97%).
Etapa 3 y siguientes
Usando como material de partida el 4-(6-bromopiridin-3-il)piperazina-1-carboxilato de terc-butilo anteriormente mencionado, se sintetizó el compuesto del título mediante un método similar al Ejemplo de Producción 1, Etapas 4
6.
Ejemplo de producción 87
Trihidrocloruro de 2-(4-{2-[5-(4-acetilpiperazin-1-il)piridin-2-il]etil}fenil)acetohidrazida
E09754868
30-10-2015
Etapa 1 Se obtuvo 1-acetil-4-piridin-3-ilpiperazina tratando 3-piperazin-4-ilpiridina con anhídrido acético. Etapa 2 Se sintetizó 1-acetil-4-(6-bromopiridin-3-il)piperazina a partir del compuesto 1-acetil-4-piridin-3-ilpiperazina
5 anteriormente mencionado bromando con N-bromosuccinimida mediante un método similar al Ejemplo de
Producción 86, Etapa 2.
Etapa 3 y siguientes El compuesto del título se sintetizó a partir del compuesto 1-acetil-4-(6-bromopiridin-3-il)piperazina anteriormente mencionado mediante un método similar al Ejemplo de Producción 1, Etapas 4 -6.
10 Tabla 1-1
Fórmula estructural del compuesto
Material de partida de anillo A Método de síntesis Propiedades MS 1H-RMN
Ejemplo de producción 1*
Método A Sólido ligeramente amarillo 312 [M+H]+ (APCI) (DMSO-d6): 10,78 (brs, 1H), 9,83 (brs, 1H), 7,46 (d, J = 8,4 Hz, 2H), 7,19 (s, 4H), 7,16 (d, J = 8,4 Hz, 2H), 3,49 (s, 2H), 2,81 (s, 4H), 2,01 (s, 3H).
*
Ejemplo de referencia Tabla 1-18
*
Ejemplo de referencia
Fórmula estructural del compuesto
Material de partida de anillo A Método de síntesis Propiedades MS 1H-RMN
Ejemplo de producción 86*
Método A Sólido amarillo ligeramente blanco 340 [M+H]+ (ESI) (DMSO-d6): 11,22 (brs, 1H), 9,31 (brs, 2H), 8,34 (d, J = 2, 8 Hz, 1H), 8,03-7,93 (m, 1H), 7,68 (d, J = 2,7 Hz, 1H), 7,267,16 (m, 4H), 3,54 (s, 2H), 3,63-3,35 (m, 4H), 3,23 (brs, 4H), 3,27-3,13 (m, 2H), 3,03-2,94 (m, 2H).
Ejemplo de producción 87
Método A Sólido amarillo 382 [M+H]+ (APCI) (DMSO-d6): 11,29 (brs, 1H), 8,26 (d, J = 2,5 Hz, 1H), 8,03 (dd, J = 9,0 Hz, 2,0 Hz, 1H), 7,72 (d, J = 9,2 Hz, 1H), 7,297,16 (m, 4H), 3,63-3,53 (m, 6H), 3,46-3,30 (m, 4H), 3,24-3,14 (m, 2H), 3,04-2,95 (m, 2H), 2,05 (s, 3H).
En la Tabla 1, el método de síntesis es como sigue.
15 Método A: condensación mediante la reacción de Sonogashira-Castero-Stephens (acetato de paladio, trifenilfosfina, diisopropilamina, acetonitrilo) → hidrogenación usando paladio sobre carbono como catalizador → desprotección, hidrocloración con disolución de cloruro de hidrógeno en dioxano.
imagen15
E09754868
30-10-2015
Tabla 3 Efecto inhibidor sobre monoamino-oxidasas de ser humano (MAO-A y MAO-B)
Ejemplo de Producción No.
Fórmula química estructural Inhibición de MAO-A IC50 (M) Inhibición de MAO-A IC50 (M)
87
> 100 > 100
Clorgilina
0,0005 Ningún dato
Pargilina
Ningún dato 0,095
Aplicabilidad industrial
5 Puesto que el compuesto de la presente invención tiene superior actividad inhibidora de la enzima VAP-1 y superior selectividad enzimática, puede eliminar los efectos secundarios y similares no preferibles para un producto farmacéutico. Por lo tanto, el compuesto es útil como un agente inhibidor de la enzima VAP-1, un medicamento para la profilaxis o el tratamiento de enfermedades asociadas con la enzima VAP-1, y similares.
Esta solicitud está basada en la solicitud de patente No. 2008-143197 registrada en Japón.
10

Claims (1)

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JP2014205687A (ja) 2014-10-30
CN102046601A (zh) 2011-05-04
RU2010154454A (ru) 2012-07-10
TWI490214B (zh) 2015-07-01
RU2526256C2 (ru) 2014-08-20
HK1210612A1 (en) 2016-04-29
JP5579168B2 (ja) 2014-08-27
HK1155750A1 (en) 2012-05-25
US9603833B2 (en) 2017-03-28
AU2009252214B2 (en) 2014-12-18
KR20110022574A (ko) 2011-03-07

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