AR038404A1 - USEFUL NICOTINAMIDE DERIVATIVES AS PDE4 INHIBITORS, PROCEDURE FOR THE PREPARATION OF THE COMPOUND AND PHARMACEUTICAL COMPOSITION THAT INCLUDES IT - Google Patents

USEFUL NICOTINAMIDE DERIVATIVES AS PDE4 INHIBITORS, PROCEDURE FOR THE PREPARATION OF THE COMPOUND AND PHARMACEUTICAL COMPOSITION THAT INCLUDES IT

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Publication number
AR038404A1
AR038404A1 ARP030100406A ARP030100406A AR038404A1 AR 038404 A1 AR038404 A1 AR 038404A1 AR P030100406 A ARP030100406 A AR P030100406A AR P030100406 A ARP030100406 A AR P030100406A AR 038404 A1 AR038404 A1 AR 038404A1
Authority
AR
Argentina
Prior art keywords
alkyl
hydroxy
formula
group
derivatives
Prior art date
Application number
ARP030100406A
Other languages
Spanish (es)
Original Assignee
Pfizer
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
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Publication date
Application filed by Pfizer filed Critical Pfizer
Publication of AR038404A1 publication Critical patent/AR038404A1/en

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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—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
    • 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3
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    • A61K31/439—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom the ring forming part of a bridged ring system, e.g. quinuclidine
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
    • C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
    • C07D451/06—Oxygen atoms
    • C07D451/10—Oxygen atoms acylated by aliphatic or araliphatic carboxylic acids, e.g. atropine, scopolamine

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Abstract

Derivados de nicotinamida y procedimientos para la preparación de dichos derivados, los intermedios utilizados en la preparación de dichos derivados, composiciones que contienen dichos derivados y los usos de dichos derivados. Los derivados de nicotinamida de acuerdo con la presente son útiles en numerosas enfermedades, trastornos y afecciones, en particular enfermedades, trastornos y afecciones inflamatorias, alérgicas y respiratorias, así como para curar heridas. Reivindicación (1): Un compuesto de fórmula (1) en la que: m es 0, 1, 2 o 3; n es 0, 1, 2 o 3; cada uno de R1 y R2 es un miembro seleccionado independientemente del grupo formado por un átomo de hidrógeno, halo, ciano, alquilo C1-4 y alcoxi C1-4; X es -O-, -S- o -NH-; R3 es un miembro seleccionado de los grupos formados por (a) fenilo, naftilo, heteroarilo y cicloalquilo C3-8, cada uno de ellos opcionalmente sustituido con 1 a 3 sustituyentes, cada uno de ellos seleccionado del grupo formado por halo, ciano, alquilo C1-4, alcoxi C1-4, tioalquilo C1-4, -C(=O)NH2, -C(=O)NH(alquilo C1-4), hidroxi, -O-C(=O)alquilo C1-4, -C(=O)-O-alquilo C1-4 e hidroxi-alquilo C1-4, o (b) los grupos bicíclicos que responden a una de las estructuras (2), a (5), en las que el símbolo ''*'' indica el punto de unión de cada fórmula parcial (2) a (5) a la porción restante de la fórmula (1); Y es un miembro seleccionado del grupo formado por las fórmulas parciales (6) a (12) en las que el símbolo ''*'' indica el punto de unión de cada fórmula parcial (6) a (12) a las porciones restantes -NH- de fórmula (1) y ''*'' indica el punto de unión de cada fórmula parcial (6) a (12) a las porciones restantes -R4 de fórmula (1); y R4 es un miembro seleccionado de los grupos que consisten en: (a) fenilo, naftilo y heteroarilo, cada uno de ellos opcionalmente sustituido con 1 a 3 sustituyentes, cada uno de ellos seleccionado del grupo formado por ácido carboxílico, -C(=O)-O-alquilo C1-4, halo, ciano, -C(=O)NH2, alquilo C1-4, alcoxi C1-4, haloalquilo C1-4, hidroxi e hidroxi-alquilo C1-4, o (b) alquilo C1-4 opcionalmente sustituido con un grupo hidroxi, ácido carboxílico, C(=O)-O-alquilo C1-4, fenilo, naftilo o heteroarilo, en donde dichos fenilo, naftilo y heteroarilo están opcionalmente sustituidos cada uno con 1 a 3 sustituyentes, cada uno de ellos seleccionado del grupo formado por ácido carboxílico, C(=O)O-alquilo C1-4, halo, ciano, -C(=O)NH2, alquilo C1-4 o alcoxi C1-4, haloalcoxi C1-4, hidroxi e hidroxi-alquilo C1-4, o sus sales y/o isómeros tautómeros, solvatos, polimorfos, variaciones isotópicas o metabolitos farmacéuticamente aceptables.Nicotinamide derivatives and procedures for the preparation of said derivatives, the intermediates used in the preparation of said derivatives, compositions containing said derivatives and the uses of said derivatives. Nicotinamide derivatives according to the present are useful in numerous diseases, disorders and conditions, in particular inflammatory, allergic and respiratory diseases, disorders and conditions, as well as for wound healing. Claim (1): A compound of formula (1) wherein: m is 0, 1, 2 or 3; n is 0, 1, 2 or 3; each of R1 and R2 is a member independently selected from the group consisting of a hydrogen atom, halo, cyano, C1-4 alkyl and C1-4 alkoxy; X is -O-, -S- or -NH-; R3 is a member selected from the groups consisting of (a) phenyl, naphthyl, heteroaryl and C3-8 cycloalkyl, each optionally substituted with 1 to 3 substituents, each selected from the group consisting of halo, cyano, alkyl C1-4, C1-4 alkoxy, C1-4 thioalkyl, -C (= O) NH2, -C (= O) NH (C1-4 alkyl), hydroxy, -OC (= O) C1-4 alkyl, - C (= O) -O-C1-4 alkyl and hydroxy-C1-4 alkyl, or (b) the bicyclic groups that respond to one of the structures (2), a (5), in which the symbol '' * '' indicates the point of attachment of each partial formula (2) to (5) to the remaining portion of the formula (1); And it is a member selected from the group consisting of partial formulas (6) to (12) in which the symbol '' * '' indicates the point of attachment of each partial formula (6) to (12) to the remaining portions - NH- of formula (1) and '' * '' indicates the point of attachment of each partial formula (6) to (12) to the remaining portions -R4 of formula (1); and R4 is a member selected from the groups consisting of: (a) phenyl, naphthyl and heteroaryl, each optionally substituted with 1 to 3 substituents, each selected from the group consisting of carboxylic acid, -C (= O) -O-C1-4 alkyl, halo, cyano, -C (= O) NH2, C1-4 alkyl, C1-4 alkoxy, C1-4 haloalkyl, hydroxy and hydroxy C1-4 alkyl, or (b) C1-4 alkyl optionally substituted with a hydroxy group, carboxylic acid, C (= O) -O-C1-4 alkyl, phenyl, naphthyl or heteroaryl, wherein said phenyl, naphthyl and heteroaryl are each optionally substituted with 1 to 3 substituents, each selected from the group consisting of carboxylic acid, C (= O) O-C1-4 alkyl, halo, cyano, -C (= O) NH2, C1-4 alkyl or C1-4 alkoxy, C1 haloalkoxy -4, hydroxy and hydroxyC 1-4 alkyl, or their salts and / or tautomeric isomers, solvates, polymorphs, isotopic variations or pharmaceutically acceptable metabolites.

ARP030100406A 2002-02-11 2003-02-10 USEFUL NICOTINAMIDE DERIVATIVES AS PDE4 INHIBITORS, PROCEDURE FOR THE PREPARATION OF THE COMPOUND AND PHARMACEUTICAL COMPOSITION THAT INCLUDES IT AR038404A1 (en)

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US6878714B2 (en) 2001-01-12 2005-04-12 Amgen Inc. Substituted alkylamine derivatives and methods of use
US7105682B2 (en) 2001-01-12 2006-09-12 Amgen Inc. Substituted amine derivatives and methods of use
US7102009B2 (en) 2001-01-12 2006-09-05 Amgen Inc. Substituted amine derivatives and methods of use
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US7307088B2 (en) 2002-07-09 2007-12-11 Amgen Inc. Substituted anthranilic amide derivatives and methods of use
US7153870B2 (en) 2003-07-25 2006-12-26 Pfizer Inc. Nicotinamide derivatives useful as PDE4 inhibitors
GB0317482D0 (en) * 2003-07-25 2003-08-27 Pfizer Ltd Nicotinamide derivatives useful as pde4 inhibitors
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JPWO2005026132A1 (en) * 2003-09-17 2007-11-08 日本新薬株式会社 CAMP substrate-specific inhibitors of phosphodiesterase
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CA2547394A1 (en) * 2004-01-09 2005-07-28 Boehringer Ingelheim International Gmbh New pharmaceutical compositions based on a scopineester and nicotinamide derivatives
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