AR061163A1 - PIRIDINONA N-ARIL AND N-HETEROARIL SUBSTITUTED DERIVATIVES FOR USE IN DISEASES MEDIATED BY MCH-1 - Google Patents

PIRIDINONA N-ARIL AND N-HETEROARIL SUBSTITUTED DERIVATIVES FOR USE IN DISEASES MEDIATED BY MCH-1

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Publication number
AR061163A1
AR061163A1 ARP070102381A ARP070102381A AR061163A1 AR 061163 A1 AR061163 A1 AR 061163A1 AR P070102381 A ARP070102381 A AR P070102381A AR P070102381 A ARP070102381 A AR P070102381A AR 061163 A1 AR061163 A1 AR 061163A1
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AR
Argentina
Prior art keywords
group
alkyl
difluorobenzyl
oxy
phenyl
Prior art date
Application number
ARP070102381A
Other languages
Spanish (es)
Original Assignee
Janssen Pharmaceutica Nv
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.)
Filing date
Publication date
Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv
Publication of AR061163A1 publication Critical patent/AR061163A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/69—Two or more oxygen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings

Abstract

Reivindicacion 1: Compuesto de acuerdo con la formula general (1) una sal de adicion de base o ácido farmacéuticamente aceptable del mismo, una forma de N-oxido del mismo o una sal de amonio cuaternario del mismo, donde A es fenilo o piridinilo; R1, R2 son cada uno, en forma independiente uno del otro, seleccionados del grupo de hidrogeno, alquilo C1-3, arilo; arilalquilo C1-3, Het, Hetalquilo C1-3, alquilcarbonilo C1-3, alquiloxicarbonilo C1-3, alquiloxi C1-3-alquilo C1-3, alquilcarbonil C1-3- alquilo C1-3, y NraRb-alquilo C1-3 o R1 y R2 se toman juntos para formar un heterociclo que contiene N, seleccionado del grupo de pirrolidinilo, imidazolidinilo, pirazolidinilo, piperidinilo, piperazinilo, morfolinilo, y tiomorfolinilo; donde cada uno de los heterociclos que contienen N arriba mencionados están opcionalmente sustituidos con k sustituyentes R3; R3 se selecciona del grupo de hidrogeno, halo, ciano, hidroxi, NRaRb, oxo, carboxilo, aminocarbonilo, nitro, tio, formilo, alquilo C1- 3, arilo, alquiloxi C1-3, y alquiloxicarbonilo C1-3; Ra y Rb cada uno, en forma independiente uno del otro, seleccionados del grupo de hidrogeno, alquiIo C1-3, arilo, Het, alquilocarbonilo C1-3, alquiloxicarbonilo C1-3, alquilsulfonilo C1-3, alquilcarbonilo C1-3-alquilo C1-3, arilalquilo C1-3 y Het alquilo C1-3; o Ra y Rb se toman juntos para formar un heterociclo que contiene N, seleccionado del grupo de pirrolidinilo, imidazolidinilo, pirazolidinilo, piperidinilo, piperazinilo, morfolinilo, 1-aza-biciclo[2.2.1]heptilo, y tiomorfolinilo; R4, R5 cada uno, en forma independiente uno del otro, seleccionados del grupo de hidrogeno, halo, ciano, hidroxi, amino, oxo, carboxilo, nitro, tio, formilo, alquilo C1-3, y alquiloxi C1-3; k es un numero entero, igual a cero, 1, 2, 3 o 4; l es un numero entero, igual a cero, 1, 2, 3 o 4; m es un numero entero, igual a cero, 1, 2 o 3; Y1, Y3 son cada uno, en forma independiente uno del otro, seleccionados del grupo de un enlace simple, O, NR7, S, SO, y SO2; donde R7 se selecciona del grupo de hidrogeno y alquilo C1-3; Y2 es un radical de hidrocarburo C1-6 saturado o insaturado, recto o ramificado, donde uno o más átomos de hidrogeno pueden ser opcionalmente reemplazado por un radical seleccionado del grupo de halo, ciano, hidroxi, amino, oxo, carboxilo, nitro, tio, y formilo; B es un anillo de 6 miembros con contenido de cero, 1, 2 o 3 átomos de nitrogeno, opcionalmente substituidos con p sustituyentes R6, cada uno en forma independiente uno del otro, seleccionados del grupo de hidrogeno, halo, ciano, hidroxi, amino, oxo, carboxilo, nitro, tio, formilo, alquilo C1-3, y alquiloxi C1-3; y donde p es un numero entero, igual a cero, 1 o 2; o dos substituyentes R6 pueden combinarse en un radical -CH2CH2CH2- o -OCH2O; alquilo es un radical de hidrocarburo saturado o insaturado, recto o ramificado que tiene el numero indicado de átomos de carbono; donde el radical puede substituirse opcionalmente por uno o más átomos de carbono con uno o más radicales seleccionados del grupo de halo, ciano, hidroxi, amino, oxo, carboxilo, nitro, tio y formilo; arilo es naftilo o fenilo, cada uno substituido opcionalmente con 1, 2 o 3 substituyentes, cada uno en forma independiente uno del otro, seleccionado del grupo de halo, ciano, hidroxi, amino, oxo, carboxilo, nitro, tio, formilo, alquilo C1-3, y alquiloxi C1-3, Het es un radical heterocíclico seleccionado del grupo de pirrolidinilo, imidazolidinilo, pirazolidinilo, piperidinilo, piperazinilo, pirrolilo, pirrolinilo, imidazolinilo, pirazolinilo, pirrolilo, imidazolilo, pirazolilo, triazolilo, piridinilo, piridazinilo, pirimidinilo, pirazinilo, triazinilo, azepilo, diazepilo, morfolinilo, tiomorfolinilo, furilo, tienilo, oxazolilo, isoxazolilo, tiazolilo, tiadiazolilo, isotiazolilo, dioxolilo, ditianilo, tetrahidrofurilo, tetrahidropiranilo, y oxadiazolilo; donde cada uno de los radicales heterocíclicos antes mencionados se substituye opcionalmente con 1, 2 o 3 substituyentes, cada uno en forma independiente uno del otro, seleccionado del grupo de halo, ciano, hidroxi, amino, oxo, carboxilo, nitro, tio, formilo, alquilo C1-3, y alquiloxi C1-3; y halo es fluor, cloro, bromo o yodo; con la salvedad de que los siguientes compuestos se excluyen: 4-[(2,4-difluorobencil)oxi]-1-[2,6-difluoro-4-[(2-hidroxietil)(metil)amino]-fenilo]-6-metilpiridina 2(1H)-ona; 4-[(2,4-difluorobencil)oxi]-1-[2,6-difluoro-4-(4- metilpiperazina-1-il)fenilo]-6-metilpiridina-2(1H)-ona; 4-[(2,4-difluorobencil)oxi]-1-[2,6-difluoro-4-(morfolina-4-ilo)fenilo]-6-metil- piridina-2(1H)-ona; 4-[(2,4-difluorobencil)oxi]-1-[4-(dimetilamino)-2,6-difluorofenilo]-6-metil-piridina-2(1H)- ona; 3-bromo-4-[(2,4-difluorobencil)oxi]-1-[2,6-difluoro-4-[(2-hidroxietilo)(metil)amino]fenil]j-6-metilpiridina-2(1H)-ona; 3-bromo-4-[(2,4-difluorobencil)oxi]-1-[2,6-difluoro-4-(4-metilpiperazina- 1-ilo)fenilo]-6-metilpiridin-2(1H)-ona; 3-bromo-4- [(2,4-difluorobencil)oxi]-1-[4-(dimetilamino)-2,6-difluorofenilo]-6-metilpiridina-2(1H)-ona; 3-bromo-4-[(2,4-difluorobencil)oxi]-1-[2,6-difluoro-4-(morfolina-4-ilo)-fenil]-6-metilpiridina-2(1H)-ona ; y 3-cloro-4-[(2,4-difluorobencil)oxi]-1-[2,6- difluoro-4-(4-metilpiperazina-1-ilo)fenil-6-metilpiridina-2(1H)-ona.Claim 1: Compound according to the general formula (1) a pharmaceutically acceptable base or acid addition salt thereof, an N-oxide form thereof or a quaternary ammonium salt thereof, wherein A is phenyl or pyridinyl; R1, R2 are each, independently of each other, selected from the hydrogen group, C1-3 alkyl, aryl; C1-3 arylalkyl, Het, C1-3 hetalkyl, C1-3 alkylcarbonyl, C1-3 alkyloxycarbonyl, C1-3 alkyloxy-C1-3 alkyl, C1-3 alkylcarbonyl C1-3 alkyl, and NraRb-C1-3 alkyl or R1 and R2 are taken together to form an N-containing heterocycle, selected from the group of pyrrolidinyl, imidazolidinyl, pyrazolidinyl, piperidinyl, piperazinyl, morpholinyl, and thiomorpholinyl; where each of the above-mentioned N-containing heterocycles are optionally substituted with k R3 substituents; R3 is selected from the group of hydrogen, halo, cyano, hydroxy, NRaRb, oxo, carboxyl, aminocarbonyl, nitro, thio, formyl, C1-3 alkyl, aryl, C1-3 alkyloxy, and C1-3 alkyloxycarbonyl; Ra and Rb each, independently of each other, selected from the group of hydrogen, C1-3 alkyl, aryl, Het, C1-3 alkylcarbonyl, C1-3 alkyloxycarbonyl, C1-3 alkylsulfonyl, C1-3 alkylcarbonyl-C1 -3, C1-3 arylalkyl and Het C1-3 alkyl; or Ra and Rb are taken together to form an N-containing heterocycle, selected from the group of pyrrolidinyl, imidazolidinyl, pyrazolidinyl, piperidinyl, piperazinyl, morpholinyl, 1-aza-bicyclo [2.2.1] heptyl, and thiomorpholinyl; R4, R5 each, independently of each other, selected from the group of hydrogen, halo, cyano, hydroxy, amino, oxo, carboxyl, nitro, thio, formyl, C1-3 alkyl, and C1-3 alkyloxy; k is an integer, equal to zero, 1, 2, 3 or 4; l is an integer, equal to zero, 1, 2, 3 or 4; m is an integer, equal to zero, 1, 2 or 3; Y1, Y3 are each, independently of each other, selected from the group of a single link, O, NR7, S, SO, and SO2; where R7 is selected from the group of hydrogen and C1-3 alkyl; Y2 is a saturated or unsaturated, straight or branched C1-6 hydrocarbon radical, where one or more hydrogen atoms can be optionally replaced by a radical selected from the group of halo, cyano, hydroxy, amino, oxo, carboxyl, nitro, thio , and formyl; B is a 6-membered ring containing zero, 1, 2 or 3 nitrogen atoms, optionally substituted with p R6 substituents, each independently from each other, selected from the group of hydrogen, halo, cyano, hydroxy, amino , oxo, carboxyl, nitro, thio, formyl, C1-3 alkyl, and C1-3 alkyloxy; and where p is an integer, equal to zero, 1 or 2; or two R6 substituents can be combined in a radical -CH2CH2CH2- or -OCH2O; alkyl is a saturated or unsaturated, straight or branched hydrocarbon radical having the indicated number of carbon atoms; wherein the radical may optionally be substituted by one or more carbon atoms with one or more radicals selected from the group of halo, cyano, hydroxy, amino, oxo, carboxyl, nitro, thio and formyl; aryl is naphthyl or phenyl, each optionally substituted with 1, 2 or 3 substituents, each independently from each other, selected from the group of halo, cyano, hydroxy, amino, oxo, carboxyl, nitro, thio, formyl, alkyl C1-3, and C1-3 alkyloxy, Het is a heterocyclic radical selected from the group of pyrrolidinyl, imidazolidinyl, pyrazolidinyl, piperidinyl, piperazinyl, pyrrolyl, pyrrolinyl, imidazolinyl, pyrazolinyl, pyrrolyl, imidazolyl, pyrazolyl, triazolyl, pyridinyl, pyridinyl, pyridainyl , pyrazinyl, triazinyl, azepyl, diazepyl, morpholinyl, thiomorpholinyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, thiadiazolyl, isothiazolyl, dioxolyl, dithianyl, tetrahydrofuryl, tetrahydropyranyl, and oxadiazolyl; wherein each of the aforementioned heterocyclic radicals is optionally substituted with 1, 2 or 3 substituents, each independently from each other, selected from the group of halo, cyano, hydroxy, amino, oxo, carboxyl, nitro, thio, formyl , C1-3 alkyl, and C1-3 alkyloxy; and halo is fluorine, chlorine, bromine or iodine; with the proviso that the following compounds are excluded: 4 - [(2,4-difluorobenzyl) oxy] -1- [2,6-difluoro-4 - [(2-hydroxyethyl) (methyl) amino] -phenyl] - 6-methylpyridine 2 (1H) -one; 4 - [(2,4-difluorobenzyl) oxy] -1- [2,6-difluoro-4- (4- methylpiperazine-1-yl) phenyl] -6-methylpyridine-2 (1H) -one; 4 - [(2,4-difluorobenzyl) oxy] -1- [2,6-difluoro-4- (morpholine-4-yl) phenyl] -6-methyl-pyridine-2 (1H) -one; 4 - [(2,4-difluorobenzyl) oxy] -1- [4- (dimethylamino) -2,6-difluorophenyl] -6-methyl-pyridine-2 (1H) -one; 3-Bromo-4 - [(2,4-difluorobenzyl) oxy] -1- [2,6-difluoro-4 - [(2-hydroxyethyl) (methyl) amino] phenyl] j-6-methylpyridine-2 (1H ) -one; 3-Bromo-4 - [(2,4-difluorobenzyl) oxy] -1- [2,6-difluoro-4- (4-methylpiperazine-1-yl) phenyl] -6-methylpyridin-2 (1H) -one ; 3-Bromo-4- [(2,4-difluorobenzyl) oxy] -1- [4- (dimethylamino) -2,6-difluorophenyl] -6-methylpyridine-2 (1H) -one; 3-Bromo-4 - [(2,4-difluorobenzyl) oxy] -1- [2,6-difluoro-4- (morpholine-4-yl) -phenyl] -6-methylpyridine-2 (1H) -one; and 3-chloro-4 - [(2,4-difluorobenzyl) oxy] -1- [2,6-difluoro-4- (4-methylpiperazine-1-yl) phenyl-6-methylpyridine-2 (1 H) -one .

ARP070102381A 2006-06-02 2007-06-01 PIRIDINONA N-ARIL AND N-HETEROARIL SUBSTITUTED DERIVATIVES FOR USE IN DISEASES MEDIATED BY MCH-1 AR061163A1 (en)

Applications Claiming Priority (2)

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EP06114917 2006-06-02
EP06123263 2006-10-31

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AR061163A1 true AR061163A1 (en) 2008-08-06

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AR (1) AR061163A1 (en)
PE (1) PE20080150A1 (en)
TW (1) TW200811146A (en)
UY (1) UY30378A1 (en)
WO (1) WO2007141200A1 (en)

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US20120316200A1 (en) * 2010-04-12 2012-12-13 Merck Sharp & Dohme Corp. Pyridone derivatives
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DK2648516T3 (en) 2010-12-06 2019-01-02 Aclaris Therapeutics Inc SUBSTITUTED PYRIDINON-PYRIDINYL COMPOUNDS
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JP6186434B2 (en) 2012-07-18 2017-08-23 サンシャイン・レイク・ファーマ・カンパニー・リミテッドＳｕｎｓｈｉｎｅ Ｌａｋｅ Ｐｈａｒｍａ Ｃｏ．，Ｌｔｄ． Nitrogen heterocyclic derivatives and their applications in medicine
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PE20080150A1 (en) 2008-04-11
UY30378A1 (en) 2008-01-02
WO2007141200A8 (en) 2008-03-27
WO2007141200A1 (en) 2007-12-13

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