AR035624A1 - COMPOUND DERIVED FROM SULFONYL AND ITS USE IN THE MANUFACTURE OF MEDICINES TO INHIBIT THE ACTIVITY OF METALOPROTEINASES OF MATRIX - Google Patents

COMPOUND DERIVED FROM SULFONYL AND ITS USE IN THE MANUFACTURE OF MEDICINES TO INHIBIT THE ACTIVITY OF METALOPROTEINASES OF MATRIX

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Publication number
AR035624A1
AR035624A1 ARP000102311A ARP000102311A AR035624A1 AR 035624 A1 AR035624 A1 AR 035624A1 AR P000102311 A ARP000102311 A AR P000102311A AR P000102311 A ARP000102311 A AR P000102311A AR 035624 A1 AR035624 A1 AR 035624A1
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AR
Argentina
Prior art keywords
group
alkyl
aryl
hydride
amino
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Application number
ARP000102311A
Other languages
Spanish (es)
Inventor
Joseph J Mcdonald
Thomas E Barta
Robert Becker
Shashidhar RAO
John N Freskos
Brent Mischke
Daniel P Getman
Gary A Decrescenzo
Clara Villamil
Luis Bedell
Original Assignee
Searle & Co
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Publication date
Application filed by Searle & Co filed Critical Searle & Co
Publication of AR035624A1 publication Critical patent/AR035624A1/en

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Abstract

Un compuesto derivado de sulfonilo que corresponde a la fórmula (1), o una sal aceptable para uso farmacéutico del mismo: donde y y z son cada uno 0 o 1 y la suma de z + y es 0 o 1; la estructura del anillo W es un anillo aromático o heteroaromático de 5 o 6 miembros; X es -CH2- o -NR9-, donde R9 se selecciona del grupo formado por un sustituyente hidruro, arilo, alquilo o arilalquilo; R1 es (i) un sustituyente que contiene un radical ciclohidrocarbilo, heterociclo, arilo o heteroarilo de 5 o 6 miembros unido directamente al grupo SO2 representado y que tiene una longitud mayor que aproximadamente la de un grupo hexilo e inferior que la de un grupo eicosilo, donde dicho R1 define un volumen tridimensional, cuando rota alrededor de un eje trazado a través de la posición 1 unida a SO2 y la posición 4 de un radical de anillo de 6 miembros o trazado a través de la posición 1 unida a SO2 y el centro de enlace 3,4 de un radical de un anillo de 5 miembros, cuya dimensión más ancha en una dirección transversal al eje de rotación es aproximadamente la de un anillo furanilo hasta aproximadamente la de dos anillos fenilo; o (ii) un grupo -NR7R8 donde R7 y R8 se seleccionan independientemente del grupo formado por hidruro, hidrocarbilo, arilo, arilo sustituido, arilhidrocarbilo, y arilhidrocarbilo sustituido; R2 y R3 se seleccionan independientemente del grupo formado por hidruro, alquilo, alquenilo, alquinilo, hidroxialquilo, Ra oxialquilo, hidroxilo, tiol, Ra tioalquilo, haloalquilo, amino, Rb Rc amino, Rb Rc aminoalquilo, RdRe aminoalcanoilo (Rb) aminoalquilo, RbRc aminoalquiloxi, RbRc aminoalquiloxialquilo, heterociclo, heterocicloalquilo, heterocicloxi, heterociclotio, heteroarilo, heteroarilalquilo, heteroariloxi, heteroariltio, o R2 y R3 junto con el átomo de carbono al cual están unidos forman un anillo carbocíclico o heterocíclico de 4 a 8 miembros, que es preferentemente un anillo de 5 o 6 miembros, donde el heteroátomo es oxígeno, azufre o nitrógeno, donde dicho heteroátomo es opcionalmente sustituido con uno o dos oxígenos cuando es azufre y es opcionalmente sustituido con una porción seleccionada del grupo formado por un grupo hidrocarbilo C1-4, ciclohidrocarbilo C3-6, hidrocarbilocarbonilo C1-4, y sulfonilo hidrocarbilo C1-4 cuando es nitrógeno; R5 y R6 se seleccionan independientemente del grupo formado por un hidruro, alquilo, cicloalquilo, acilalquilo, halo, nitro, hidroxilo, ciano, alcoxi, haloalquilo, haloalquiloxi, hidroxialquilo, un sustituyente RbRc aminoalquilo, tiol, alquiltio, ariltio, cicloalquiltio, cicloalcoxi, alcoxialcoxi, perfluoroalquilo, haloalquilo, heterocicloxi y un sustituyente RbRc aminoalquiloxi; o R5 y R6 junto con los átomos a los cuales están unidos forman otro anillo carbocíclico o heterocíclico alifático o aromático de 5 o 7 miembros; y R20 es (a) -O-R21, donde R21 se selecciona del grupo formado por un grupo hidruro, alquilo C1-6, arilo, ar-alquilo C1-6 y un catión aceptable para uso farmacéutico; (b) -NR13-O-R22 donde R22 es un grupo protector selectivamente removible y R13 es un hidruro, alquilo C1-6 o grupo bencilo; (c) -NR13-O-R14, donde R13 tiene los valores definidos anteriormente y R14 es hidruro, un catión aceptable para uso farmacéutico o C(V)R15 donde V es O o S y R15 se selecciona del grupo formado por alquilo C1-6, arilo, alcoxi C1-6, heteroaril-alquilo C1-6, cicloalquil C3-8-alquilo C1-6, ariloxi, ar -alcoxi C1-6, ar-alquilo C1-6, heteroarilo y un grupo amino alquilo C1-6 donde el nitrógeno del amino alquilo C1-6 es (i) insustituido o (ii) sustituido con uno o dos sustituyentes independientemente seleccionados del grupo formado por un radical alquilo C1-6, arilo, ar-alquilo C1-6, cicloalquil C3-8-alquilo C1-6, ar-alcoxicarbonilo C1-6, alcoxicarbonilo C1-6, y alcanoílo C1-6, o (iii) donde el nitrógeno del amino alquilo C1-6 y dos sustituyentes unidos al mismo forman un anillo heterociclo o heteroarilo de 5 a 8 miembros, o (d) -NR23R24, donde R23 y R24 se seleccionan independientemente del grupo formado por un grupo hidruro, alquilo C1-6, amino-alquilo C1-6, hidroxi-alquilo C1-6, arilo, y un grupo ar-alquilo C1-6, o R23 y R24 junto con el átomo de nitrógeno representado forman un anillo de 5 a 8 miembros que contiene 0 o un heteroátomo adicional que es oxígeno, nitrógeno o azufre; donde: Ra se selecciona del grupo formado por un hidruro, alquilo, alquenilo, alquinilo, arilalquilo, arilo, alcanoílo, aroílo, arilalquilcarbonilo, RbRc aminoalquilo, alcoxialquilo, haloalquilo y un grupo arilalquiloxi; Rb y Rc se seleccionan independientemente del grupo formado por un hidruro, alcanoílo, arilalquilo, aroílo, bisalcoxialquilo, alquilo, haloalquilo, perfluoroalquilo, trifluorometilalquilo, perfluoroalcoxialquilo, alcoxialquilo, cicloalquilo, heterocicloalquilo, heterocicloalquilcarbonilo, arilo, heterociclo, heteroarilo, cicloalquilalquilo, ariloxialquilo, heteroariloxialquilo, heteroarilalcoxialquilo, heteroariltioalquilo, arilsulfonilo, aralcanoílo, alquilsulfonilo, heteroarilsulfonilo, carboxialquilo, alcoxicarbonilalquilo, aminocarbonilo, alquiliminocarbonilo, ariliminocarbonilo, heterocicloiminocarbonilo, ariltioalquilo, alquiltioalquilo, ariltioalquenilo, alquiltioalquenilo, heteroarilalquilo, haloalcanoílo, hidroxialcanoílo, tioalcanoílo, alquenilo, alquinilo, alcoxialquilo, alcoxicarbonilo, ariloxicarbonilo, aminoalquilcarbonilo, hidroxialquilo, aminoalquilo, aminoalquilsulfonilo, aminosulfonilo donde el nitrógeno del amino es (i) insustituido o (ii) sustituido independientemente con uno o dos radicales Rd, o los sustituyentes en el grupo amino tomados junto con el nitrógeno del amino forman un grupo heterociclo saturado o parcialmente insaturado opcionalmente sustituido con 1, 2 o 3 grupos seleccionados independientemente entre sustituyentes Rd o un grupo heteroarilo opcionalmente sustituido con 1, 2 o 3 grupos seleccionados independientemente entre sustituyentes Rf; Rc y Re se seleccionan independientemente del grupo formado por un hidruro, alquilo, alquenilo, alquinilo, arilalquilo, arilo, alcanoílo, aroílo, arilalquilcarbonilo, alcoxicarbonilo y un grupo arilalquiloxicarbonilo; y Rf se selecciona del grupo formado por un grupo nitro, hidroxi, alquilo, halógeno, arilo, alcoxi, ciano, y un RdRe amino. Estos compuestos se usan en la fabricación de medicamentos para inhibir la actividad de metaloproteinasas de matriz en un huésped que padece una afección relacionada con la actividad patológica de metaloproteinasas de matriz.A sulfonyl derivative compound corresponding to formula (1), or a salt acceptable for pharmaceutical use thereof: where y and z are each 0 or 1 and the sum of z + y is 0 or 1; the structure of the W ring is an aromatic or heteroaromatic ring of 5 or 6 members; X is -CH2- or -NR9-, where R9 is selected from the group consisting of a hydride, aryl, alkyl or arylalkyl substituent; R1 is (i) a substituent containing a 5- or 6-membered cyclohydrocarbyl, heterocycle, aryl or heteroaryl radical attached directly to the represented SO2 group and having a length greater than about that of a hexyl group and less than that of an eicosyl group , wherein said R1 defines a three-dimensional volume, when it rotates about an axis drawn through position 1 attached to SO2 and position 4 of a 6-membered ring radical or drawn through position 1 attached to SO2 and the link center 3.4 of a 5-membered ring radical, whose widest dimension in a direction transverse to the axis of rotation is approximately that of a furanyl ring to approximately that of two phenyl rings; or (ii) a group -NR7R8 where R7 and R8 are independently selected from the group consisting of hydride, hydrocarbyl, aryl, substituted aryl, arylhydrocarbyl, and substituted arylhydrocarbyl; R2 and R3 are independently selected from the group consisting of hydride, alkyl, alkenyl, alkynyl, hydroxyalkyl, Ra oxyalkyl, hydroxyl, thiol, Ra thioalkyl, haloalkyl, amino, Rb Rc amino, Rb Rc aminoalkyl, RdRe aminoalkanoyl (Rb) aminoalkyl, RbRc aminoalkyloxy, RbRc aminoalkyloxyalkyl, heterocycle, heterocycloalkyl, heterocycloxy, heterocyclyl, heteroaryl, heteroarylalkyl, heteroaryloxy, heteroarylthio, or R2 and R3 together with the carbon atom to which they are attached form a 4 to 8 membered carbocyclic or heterocyclic ring, which is preferably a 5 or 6 member ring, where the heteroatom is oxygen, sulfur or nitrogen, where said heteroatom is optionally substituted with one or two oxygen when it is sulfur and is optionally substituted with a portion selected from the group consisting of a C1-4 hydrocarbyl group , C3-6 cyclohydrocarbyl, C1-4 hydrocarbylcarbonyl, and C1-4 sulfonyl hydrocarbyl when it is nitrogen; R5 and R6 are independently selected from the group consisting of a hydride, alkyl, cycloalkyl, acylalkyl, halo, nitro, hydroxyl, cyano, alkoxy, haloalkyl, haloalkyloxy, hydroxyalkyl, a substituent RbRc aminoalkyl, thiol, alkylthio, arylthio, cycloalkylthio, cycloalkoxy, alkoxyalkoxy, perfluoroalkyl, haloalkyl, heterocycloxy and an RbRc aminoalkyloxy substituent; or R5 and R6 together with the atoms to which they are attached form another aliphatic or aromatic carbocyclic or heterocyclic ring of 5 or 7 members; and R20 is (a) -O-R21, where R21 is selected from the group consisting of a hydride group, C1-6 alkyl, aryl, ar-C1-6 alkyl and a cation acceptable for pharmaceutical use; (b) -NR13-O-R22 where R22 is a selectively removable protective group and R13 is a hydride, C1-6 alkyl or benzyl group; (c) -NR13-O-R14, where R13 has the values defined above and R14 is hydride, a cation acceptable for pharmaceutical use or C (V) R15 where V is O or S and R15 is selected from the group consisting of C1 alkyl -6, aryl, C 1-6 alkoxy, heteroaryl-C 1-6 alkyl, C 3-8 cycloalkyl-C 1-6 alkyl, aryloxy, C 1-6 alkoxy, C 1-6 alkyl, heteroaryl and a C 1-6 alkyl amino group -6 where the nitrogen of the amino C1-6 alkyl is (i) unsubstituted or (ii) substituted with one or two substituents independently selected from the group consisting of a C1-6 alkyl radical, aryl, ar- C1-6 alkyl, C3 cycloalkyl -8-C 1-6 alkyl, C 1-6 ar-alkoxycarbonyl, C 1-6 alkoxycarbonyl, and C 1-6 alkanoyl, or (iii) where the C 1-6 alkyl amino nitrogen and two substituents attached thereto form a heterocycle ring or 5-8 membered heteroaryl, or (d) -NR23R24, where R23 and R24 are independently selected from the group consisting of a hydride group, C1-6 alkyl, amino- C1-6 alkyl, hydroxy-C1-6 alkyl, aryl or, and an ar-C1-6 alkyl group, or R23 and R24 together with the nitrogen atom represented form a 5- to 8-membered ring containing 0 or an additional heteroatom that is oxygen, nitrogen or sulfur; where: Ra is selected from the group consisting of a hydride, alkyl, alkenyl, alkynyl, arylalkyl, aryl, alkanoyl, aroyl, arylalkylcarbonyl, RbRc aminoalkyl, alkoxyalkyl, haloalkyl and an arylalkyl group; Rb and Rc are independently selected from the group consisting of a hydrido, alkanoyl, arylalkyl, aroyl, bisalcoxialquilo, alkyl, haloalkyl, perfluoroalkyl, trifluoromethylalkyl, perfluoroalkoxyalkyl, alkoxyalkyl, cycloalkyl, heterocycloalkyl, heterocycloalkylcarbonyl, aryl, heterocyclo, heteroaryl, cycloalkylalkyl, aryloxyalkyl, heteroaryloxyalkyl , heteroarylalkoxyalkyl, heteroarylthioalkyl, arylsulfonyl, aralkanoyl, alkylsulfonyl, heteroarylsulfonyl, carboxyalkyl, alkoxycarbonylalkyl, aminocarbonyl, alquiliminocarbonilo, ariliminocarbonilo, heterocicloiminocarbonilo, arylthioalkyl, alkylthioalkyl, ariltioalquenilo, alkylthioalkenyl, heteroarylalkyl, haloalkanoyl, hydroxyalkanoyl, thioalkanoyl, alkenyl, alkynyl, alkoxyalkyl, alkoxycarbonyl, aryloxycarbonyl , aminoalkylcarbonyl, hydroxyalkyl, aminoalkyl, aminoalkylsulfonyl, aminosulfonyl where the amino nitrogen is (i) unsubstituted or (ii) independently substituted entirely with one or two radicals Rd, or the substituents in the amino group taken together with the amino nitrogen form a saturated or partially unsaturated heterocycle group optionally substituted with 1, 2 or 3 groups independently selected from Rd substituents or an optionally substituted heteroaryl group with 1, 2 or 3 groups independently selected from Rf substituents; Rc and Re are independently selected from the group consisting of a hydride, alkyl, alkenyl, alkynyl, arylalkyl, aryl, alkanoyl, aroyl, arylalkylcarbonyl, alkoxycarbonyl and an arylalkyloxycarbonyl group; and Rf is selected from the group consisting of a nitro, hydroxy, alkyl, halogen, aryl, alkoxy, cyano, and an amino RdRe group. These compounds are used in the manufacture of medicaments to inhibit the activity of matrix metalloproteinases in a host suffering from a condition related to the pathological activity of matrix metalloproteinases.

ARP000102311A 1999-05-12 2000-05-12 COMPOUND DERIVED FROM SULFONYL AND ITS USE IN THE MANUFACTURE OF MEDICINES TO INHIBIT THE ACTIVITY OF METALOPROTEINASES OF MATRIX AR035624A1 (en)

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