AR055368A1 - DERIVATIVES OF PIRAZOL, PHARMACEUTICAL COMPOSITIONS THAT CONTAIN THEM AND THEIR USE IN THE PREPARATION OF MEDICINES FOR THE TREATMENT OF NEURODEGENERATIVE DISEASES AND OBESITY - Google Patents

DERIVATIVES OF PIRAZOL, PHARMACEUTICAL COMPOSITIONS THAT CONTAIN THEM AND THEIR USE IN THE PREPARATION OF MEDICINES FOR THE TREATMENT OF NEURODEGENERATIVE DISEASES AND OBESITY

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AR055368A1
AR055368A1 ARP060103449A ARP060103449A AR055368A1 AR 055368 A1 AR055368 A1 AR 055368A1 AR P060103449 A ARP060103449 A AR P060103449A AR P060103449 A ARP060103449 A AR P060103449A AR 055368 A1 AR055368 A1 AR 055368A1
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Argentina
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pyrazol
methyl
dichlorophenyl
phenyl
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ARP060103449A
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Astrazeneca Ab
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    • C07D401/14—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 three or more hetero rings
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    • 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
    • C07D401/12—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 chain containing hetero atoms as chain links

Abstract

Las sales de 1,5-diarilpirazol-3-carboxamidas y procesos para preparar ese tipo de compuestos, su utilizacion en el tratamiento de la obesidad, trastornos siquiátricos y neurologicos y a composiciones farmacéuticas que las contienen. Reivindicacion 1: Un compuesto seleccionado entre: 4-[2-(2,4-diclorofenil)-4-metil-5-(piperidin-1-ilcarbamoil)-2H-pirazol-3-il]fenil éster del ácido butan-1-sulfonico; piperidin-1-ilamida del ácido l-(2,4-diclorofenil)-4-metil-5-[4-(4,4,4-trifluorbutoxi)fenil]-lH- pirazol-3-carboxílico; 4-[2-(2,4-dicloro-fenil)-4-metil-5-(piperidin-l-ilcarbamoil)2H-pirazol-3-il]-fenil éster del ácido propan-1-sulfonico; 4-[2-(2,4-diclorofenil)-4-metil-5-(morfolin-4-ilcarbamoil)-2H-pirazol-3-il]fenil éster del ácido propan-1- sulfonico; 4-[2-(2,4-diclorofenil)-4-metil-5-(piperidin-l-ilcarbamoil)-2H-pirazol-3-il]fenil éster del ácido 3,3,3-trifluorpropan-1-sulfonico; 4-[2-(2,4-diclorofenil)-4-metil-5-(piperidin-l-ilcarbamoil)-2H-pirazol-3-il]fenil éster del ácido 4,4,4- trifluorbutan-l-sulfonico; [2-(2,4-diclorofenil)-4-metil-5-(piperidin-l-ilcarbamoil)-2H-pirazol-3-il]-2,6-difluorfenil éster del ácido propan-1-sulfonico; 4-[2-(2,4-diclorofenil)-5-(piperidin-l-ilcarbamoil)-2H-pirazol-3-il]fenil éster del ácido propan-1-sulfonico; 4-[4-bromo-2-(2,4-diclorofenil)-5-(piperidin-1-ilcarbamoil)-2H-pirazol-3-il]fenil éster del ácido propan-1-sulfonico; 1-{[(1-(2,4-diclorofenil)-4-metil-5-{4[(propilsulfonil)oxi]fenil}-IH-pirazol-3- il)carbonil]amino}ciclopentancarboxilato de metilo; 4-[2-(2,4-diclorofenil)-4-metil-5-(piperidina-1-ilcarbamoil)-2H-pirazol-3-il]-fenil éster propil éster del ácido carbonico; 4-{l-(2,4-diclorofenil)-4-metil-3-[(piperidin-l-ilamino)carbonil]-lH- pirazol-5-il}fenil tiofen-2-sulfonato; 4-{1-(2,4-diclorofenil)-4-metil-3-[(piperidin-1-ilamino)carbonil]-lH-pirazol-5-il}fenil piridin-3-sulfonato; [2-(4-{l-(2,4-diclorofenil)-4-metil-3-[(piperidin-l-ilamino)carbonil]-lH-pirazol-5- il}fenoxi)etil]etilcarbamato de terc-butilo; 4-{1-(2,4-diclorofenil)-4-metil-3-[(piperidin-l-ilamino)carbonil]-lH-pirazol-5-il}fenil 3-metilbutan-1-sulfonato; 4-{l-(2,4-diclorofenil)-4-metil-3-[(piperidin-l-ilamino)carbonil]-lH-pirazol-5-il}fenil 3,3-dimetilbutan-l-sulfonato; l-(2,4-diclorofenil)-5-{4-[2-(l,3-dioxolan-2-il)etoxi]fenil}-4-metil-N-piperidin-1-il-lH-pirazol-3-carboxamida; 4-[2-(2,4-dicloro-3-fluorfenil)-4-metil-5-(piperidin-l-ilcarbamoil)-2H-pirazol-3-il]fenil éster del ácido propan-1-sulfonico; 4-[2-(2,4-diclorofenil)-4-metil-5-(piperidin-1-ilcarbamoil)-2H-pirazol-3-il]fenil éster del ácido 5-clorotiofen-2-sulfonico; en la forma de una sal metanosulfonato, una sal hemi-1,5-naftalenodisulfonato, una sal de ácido 1,2- etanodisulfonico, una sal clorhidrato o una sal hidrogeno sulfato aunque excluyendo clorhidrato del 4-[2-(2,4-diclorofenil)-4-metil-5-(piperidin-1-ilcarbamoil)-2H-pirazol-3-il]fenil éster del ácido piridin-3-sulfonico. Reivindicacion 3: Un compuesto de formula (1), en la cual, R1 representa: a) un grupo de alcoxi C1-3 substituido con uno o más de los siguientes: i) fluor; ii) un grupo NRcRd, donde Rc y Rd representan independientemente H, un grupo alcoxicarbonilo C1-6 siempre que uno de Rc y Rd no sea H; o iii) un grupo 1,3-dioxolan-2-ilo; b) R1 representa un grupo alcoxi C4-6 opcionalmente sustituido con uno o más de los siguientes: i) fluor; ii) un grupo NRcRd, donde Rc y Rd representan independientemente H, un grupo alquilo C1-6 o grupo alcoxicarbonilo C1-6 siempre que uno de Rc y Rd no sea H; o iii) un grupo l,3-dioxolan-2-il; c) un grupo de formula fenil(CH2)pO-, donde p es 1, 2 o 3 y el anillo fenilo está opcionalmente sustituido con 1, 2 o 3 grupos representados por Z; d) un grupo R5S(O)2O o R5S(O)2NH, donde R5 representa un grupo de alquilo C1-6 opcionalmente sustituido con uno o más fluor, o R5 representa fenilo o un grupo heteroarilo cada uno de los cuales está opcionalmente sustituido con 1, 2 o 3 grupos representados por Z; e) un grupo de formula (R6)3Si, donde R6 representa un grupo alquilo C1-6 el cual puede ser igual o diferente o f) un grupo del formula RbO(CO)O, Rb representa un grupo alquilo C1-6 opcionalmente sustituido con uno o más fluor; Ra representa halo, un grupo alquilo C1-3 o un grupo alcoxi C1-3; m es 0, 1, 2 o 3; R2 representa un grupo alquilo C1-3, un grupo alcoxi C1-3, hidroxi, nitro, ciano o halo; n es 0, 1, 2 o 3; R3 representa: a) un grupo X-Y-NR7R8, donde X es CO o SO2; Y está ausente o representa NH opcionalmente sustituido con un grupo alquilo C1-3; y R7 y R8 representan independientemente: un grupo alquilo C1-6 opcionalmente sustituido con 1, 2, o 3 grupos representados por W; un grupo del cicloalquilo C3- 15 opcionalmente sustituido con 1, 2, o 3 grupos representados por W; un grupo (cicloalquilC3-15)alquilenoC1-3 opcionalmente sustituido con 1, 2, o 3 grupos representados por W; un grupo -(CH2)r(fenil)s, donde r es 0, 1, 2, 3 o 4, s es 1 cuando r es 0 de otro modo s es 1 o 2 y los grupos fenilo están opcional e independientemente sustituidoscon uno, dos o tres grupos representados por Z; un grupo heterocíclico saturado de 5 a 8 miembros que contiene un nitrogeno y opcionalmente uno de los siguientes: oxígeno, azufre o un adicional donde el grupo heterocíclico está opcionalmente sustituido con uno o más grupos alquilo C1-3, hidroxi o bencilo; un grupo -(CH2)tHet, donde t es 0, 1, 2, 3 o 4, y la cadena alquileno es opcionalmente sustituida con uno o más grupos alquilo C1-3 y Het representa un heterociclo aromático opcionalmente sustituido con uno, dos o tres grupos seleccionados de un grupo alquilo C1-5, un grupo alcoxi C1-5 o halo donde el grupo alquilo y alcoxi están opcional e independientemente sustituidos con uno o más fluor; o R7 representa H y R8 es segun lo definido anteriormente; o R7 y R8 junto con el átomo de nitrogeno al cual están unidos representan un grupo heterocíclico saturado o parcialmente insaturado, de 5 a 8 miembros, que contiene un nitrogeno y opcionalmente uno de los siguientes: oxígeno, azufre o un nitrogeno adicional; donde el grupo heterocíclico está opcionalmente sustituido con uno o más grupos alquiloC1-3, hidroxi, fluor o; bencilo; o b) oxazolilo, isoxazolilo, tiazolilo, isotiazolilo, oxadiazolilo, tiadiazolilo, pirrolilo, pirazolilo, imidazolilo, triazolilo, tetrazolilo, tienilo, furilo u oxazolinilo, cada uno opcionalmente sustituido con 1, 2 o 3 grupos Z; R4 representa H, halo, hidroxi, ciano, un grupo alquilo C1-6, un grupo alcoxi C1-6 o un grupo alcoxiC1-6-alquilenoC1-6, el cual contiene un máximo de 6 átomos de carbono, cada uno de dichos grupos está opcionalmente sustituido con uno o más fluor o ciano; Z representa un grupo alquilo C1-3, un grupo alcoxiC1-3, hidroxi, halo, trifluormetilo, trifluormetiltio, difluormetoxi, trifluormetoxi, trifluormetilsulfonil, nitro, amino, mono o di-alquilaminoC1-3, alquilsulfonilo C1-3, alcoxicarbonilo C1- 3, carboxi, ciano, carbamoilo, mono o dialquilC1-3-carbamoilo y acetilo; y W representa hidroxi, fluor, un grupo alquilo C1-3, un grupo alcoxi C1-3, amino, mono o di-alquilaminoC1-3, un grupo alcoxicarbonilo C1-6 o una amina heterocíclica seleccionada entre morfolinilo, pirrolidinilo, piperidinilo o piperazinilo donde la amina heterocíclica es opcionalmente sustituida con un grupo alquilo C1-3 o hidroxilo; aunque excluyendo 1,1-dimetiletil [2-[4-[3-[etilmetilamino)carbonil]-l(4- metoxifenil)-lH-pirazol-5-il]fenooxi]etil]carbamato y 1,1-dimetiletil [2-[4-[1-(4-metoxifenil)-3-(1-piperidinilcarbonil)-lH-pirazol-5-il]etil]carbamato; en la forma de una sal metanosulfonato, una sal hemi-1,5-naftalenodisulfonato, o una sal del sal ácido 1,2-etanodisulfonico.The salts of 1,5-diarylpyrazol-3-carboxamides and processes to prepare such compounds, their use in the treatment of obesity, psychiatric and neurological disorders and pharmaceutical compositions containing them. Claim 1: A compound selected from: 4- [2- (2,4-Dichlorophenyl) -4-methyl-5- (piperidin-1-ylcarbamoyl) -2H-pyrazol-3-yl] phenyl ester of butan-1 acid -sulfonic; l- (2,4-Dichlorophenyl) -4-methyl-5- [4- (4,4,4-trifluorbutoxy) phenyl] -lH-pyrazol-3-carboxylic acid piperidine-1-ylamide; Propan-1-sulfonic acid 4- [2- (2,4-dichloro-phenyl) -4-methyl-5- (piperidin-l-ylcarbamoyl) 2H-pyrazol-3-yl] -phenyl ester; 4- [2- (2,4-Dichlorophenyl) -4-methyl-5- (morpholin-4-ylcarbamoyl) -2H-pyrazol-3-yl] phenyl ester of propan-1-sulfonic acid; 3,3,3-Trifluorpropan-1-sulfonic acid 4- [2- (2,4-dichlorophenyl) -4-methyl-5- (piperidin-l-ylcarbamoyl) -2H-pyrazol-3-yl] phenyl ester ; 4,4,4-Trifluorbutan-1-sulfonic acid 4- [2- (2,4-dichlorophenyl) -4-methyl-5- (piperidin-l-ylcarbamoyl) -2H-pyrazol-3-yl] phenyl ester ; [2- (2,4-Dichlorophenyl) -4-methyl-5- (piperidin-l-ylcarbamoyl) -2H-pyrazol-3-yl] -2,6-difluorphenyl ester of propan-1-sulfonic acid; 4- [2- (2,4-Dichlorophenyl) -5- (piperidin-l-ylcarbamoyl) -2H-pyrazol-3-yl] phenyl ester of propan-1-sulfonic acid; Propan-1-sulfonic acid 4- [4-bromo-2- (2,4-dichlorophenyl) -5- (piperidin-1-ylcarbamoyl) -2H-pyrazol-3-yl] phenyl ester; Methyl 1 - {[(1- (2,4-dichlorophenyl) -4-methyl-5- {4 [(propylsulfonyl) oxy] phenyl} -IH-pyrazol-3-yl) carbonyl] amino} cyclopentanecarboxylate; 4- [2- (2,4-Dichlorophenyl) -4-methyl-5- (piperidine-1-ylcarbamoyl) -2H-pyrazol-3-yl] -phenyl ester propyl ester of carbonic acid; 4- {l- (2,4-dichlorophenyl) -4-methyl-3 - [(piperidin-l-ylamino) carbonyl] -lH- pyrazol-5-yl} phenyl thiophene-2-sulfonate; 4- {1- (2,4-Dichlorophenyl) -4-methyl-3 - [(piperidin-1-ylamino) carbonyl] -lH-pyrazol-5-yl} phenyl pyridin-3-sulfonate; [2- (4- {l- (2,4-Dichlorophenyl) -4-methyl-3 - [(piperidin-l-ylamino) carbonyl] -lH-pyrazol-5-yl} phenoxy) ethyl] ethylcarbamate butyl; 4- {1- (2,4-Dichlorophenyl) -4-methyl-3 - [(piperidin-l-ylamino) carbonyl] -lH-pyrazol-5-yl} phenyl 3-methylbutan-1-sulfonate; 4- {l- (2,4-dichlorophenyl) -4-methyl-3 - [(piperidin-l-ylamino) carbonyl] -lH-pyrazol-5-yl} phenyl 3,3-dimethylbutan-l-sulfonate; l- (2,4-dichlorophenyl) -5- {4- [2- (l, 3-dioxolan-2-yl) ethoxy] phenyl} -4-methyl-N-piperidin-1-yl-lH-pyrazole- 3-carboxamide; Propan-1-sulfonic acid 4- [2- (2,4-dichloro-3-fluorphenyl) -4-methyl-5- (piperidin-l-ylcarbamoyl) -2H-pyrazol-3-yl] phenyl ester; 5-Chlorothiophene-2-sulfonic acid 4- [2- (2,4-dichlorophenyl) -4-methyl-5- (piperidin-1-ylcarbamoyl) -2H-pyrazol-3-yl] phenyl ester; in the form of a methanesulfonate salt, a hemi-1,5-naphthalenedisulfonate salt, a 1,2-ethanedisulfonic acid salt, a hydrochloride salt or a hydrogen sulfate salt although excluding 4- [2- (2,4-) hydrochloride dichlorophenyl) -4-methyl-5- (piperidin-1-ylcarbamoyl) -2H-pyrazol-3-yl] phenyl ester of pyridin-3-sulfonic acid. Claim 3: A compound of formula (1), wherein R1 represents: a) a C1-3 alkoxy group substituted with one or more of the following: i) fluorine; ii) an NRcRd group, where Rc and Rd independently represent H, a C1-6 alkoxycarbonyl group provided that one of Rc and Rd is not H; or iii) a 1,3-dioxolan-2-yl group; b) R1 represents a C4-6 alkoxy group optionally substituted with one or more of the following: i) fluorine; ii) an NRcRd group, where Rc and Rd independently represent H, a C1-6 alkyl group or C1-6 alkoxycarbonyl group provided that one of Rc and Rd is not H; or iii) a group l, 3-dioxolan-2-yl; c) a group of formula phenyl (CH2) pO-, where p is 1, 2 or 3 and the phenyl ring is optionally substituted with 1, 2 or 3 groups represented by Z; d) an R5S (O) 2O or R5S (O) 2NH group, where R5 represents a C1-6 alkyl group optionally substituted with one or more fluorine, or R5 represents phenyl or a heteroaryl group each of which is optionally substituted with 1, 2 or 3 groups represented by Z; e) a group of formula (R6) 3Si, where R6 represents a C1-6 alkyl group which may be the same or different from) a group of the formula RbO (CO) O, Rb represents a C1-6 alkyl group optionally substituted with one or more fluorine; Ra represents halo, a C1-3 alkyl group or a C1-3 alkoxy group; m is 0, 1, 2 or 3; R2 represents a C1-3 alkyl group, a C1-3 alkoxy, hydroxy, nitro, cyano or halo group; n is 0, 1, 2 or 3; R3 represents: a) a group X-Y-NR7R8, where X is CO or SO2; Y is absent or represents NH optionally substituted with a C1-3 alkyl group; and R7 and R8 independently represent: a C1-6 alkyl group optionally substituted with 1, 2, or 3 groups represented by W; a C3-15 cycloalkyl group optionally substituted with 1, 2, or 3 groups represented by W; a group (C3-15 cycloalkyl) C1-3alkylene optionally substituted with 1, 2, or 3 groups represented by W; a group - (CH2) r (phenyl) s, where r is 0, 1, 2, 3 or 4, s is 1 when r is 0 otherwise s is 1 or 2 and the phenyl groups are optionally and independently substituted with one , two or three groups represented by Z; a saturated 5- to 8-membered heterocyclic group containing a nitrogen and optionally one of the following: oxygen, sulfur or an additional where the heterocyclic group is optionally substituted with one or more C1-3 alkyl, hydroxy or benzyl groups; a group - (CH2) tHet, where t is 0, 1, 2, 3 or 4, and the alkylene chain is optionally substituted with one or more C1-3 alkyl groups and Het represents an aromatic heterocycle optionally substituted with one, two or three groups selected from a C1-5 alkyl group, a C1-5 alkoxy group or halo where the alkyl and alkoxy group are optionally and independently substituted with one or more fluorine; or R7 represents H and R8 is as defined above; or R7 and R8 together with the nitrogen atom to which they are attached represent a saturated or partially unsaturated heterocyclic group, of 5 to 8 members, which contains a nitrogen and optionally one of the following: oxygen, sulfur or an additional nitrogen; wherein the heterocyclic group is optionally substituted with one or more C1-3 alkyl, hydroxy, fluorine or groups; benzyl; or b) oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, thienyl, furyl or oxazolinyl, each optionally substituted with 1, 2 or 3 Z groups; R4 represents H, halo, hydroxy, cyano, a C1-6 alkyl group, a C1-6 alkoxy group or a C1-6 alkoxyC1-6 group, which contains a maximum of 6 carbon atoms, each of said groups it is optionally substituted with one or more fluorine or cyano; Z represents a C1-3 alkyl group, a C1-3 alkoxy group, hydroxy, halo, trifluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, trifluoromethylsulfonyl, nitro, amino, mono or di-C 1-3 alkylamino, C1-3 alkylsulfonyl, C1-3 alkoxycarbonyl , carboxy, cyano, carbamoyl, mono or dialkylC1-3-carbamoyl and acetyl; and W represents hydroxy, fluorine, a C1-3 alkyl group, a C1-3 alkoxy, amino, mono or di-C 1-3 alkylamino group, a C1-6 alkoxycarbonyl group or a heterocyclic amine selected from morpholinyl, pyrrolidinyl, piperidinyl or piperazinyl wherein the heterocyclic amine is optionally substituted with a C1-3 alkyl or hydroxyl group; although excluding 1,1-dimethylethyl [2- [4- [3- [ethylmethylamino) carbonyl] -l (4- methoxyphenyl) -lH-pyrazol-5-yl] phenoxy] ethyl] carbamate and 1,1-dimethylethyl [2 - [4- [1- (4-Methoxyphenyl) -3- (1-piperidinylcarbonyl) -lH-pyrazol-5-yl] ethyl] carbamate; in the form of a methanesulfonate salt, a hemi-1,5-naphthalenedisulfonate salt, or a salt of the 1,2-ethanedisulfonic acid salt.

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