AR031098A1 - HYDROXIFENIL UREA COMPOUNDS REPLACED WITH SULFONAMIDS, PHARMACEUTICAL COMPOSITIONS THAT INCLUDE THEM, AND USE OF THE SAME IN THE MANUFACTURE OF MEDICINES TO TREAT A DISEASE MEDIATED BY A CHEMIOQUINE - Google Patents

HYDROXIFENIL UREA COMPOUNDS REPLACED WITH SULFONAMIDS, PHARMACEUTICAL COMPOSITIONS THAT INCLUDE THEM, AND USE OF THE SAME IN THE MANUFACTURE OF MEDICINES TO TREAT A DISEASE MEDIATED BY A CHEMIOQUINE

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Publication number
AR031098A1
AR031098A1 ARP010101183A ARP010101183A AR031098A1 AR 031098 A1 AR031098 A1 AR 031098A1 AR P010101183 A ARP010101183 A AR P010101183A AR P010101183 A ARP010101183 A AR P010101183A AR 031098 A1 AR031098 A1 AR 031098A1
Authority
AR
Argentina
Prior art keywords
alkyl
heteroaryl
heterocycle
optionally substituted
aryl
Prior art date
Application number
ARP010101183A
Other languages
Spanish (es)
Original Assignee
Smithkline Beecham Corp
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 Smithkline Beecham Corp filed Critical Smithkline Beecham Corp
Publication of AR031098A1 publication Critical patent/AR031098A1/en

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    • C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
    • C07D295/26—Sulfur atoms
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    • C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C275/30—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by halogen atoms, or by nitro or nitroso groups
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    • C07C311/45—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups at least one of the singly-bound nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfonamides
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    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members 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
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  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Rheumatology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Molecular Biology (AREA)
  • Biotechnology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Toxicology (AREA)
  • Pain & Pain Management (AREA)
  • Psychiatry (AREA)
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  • Vascular Medicine (AREA)

Abstract

Compuestos de hidroxifenil urea sustituidos con sulfonamidas, de formula (1) o sales farmacéuticamente aceptables de los mismos, en donde: Rb es independientemente seleccionado del grupo que consiste en hidrogeno, NR6R7, OH, ORa, alquilo C1-5, arilo, aril-alquilo C1-4, aril-alquenilo C2-4, cicloalquilo, cicloalquil-alquilo C1-5, heteroarilo, heteroaril-alquilo C1-4, heteroaril-alquenilo C2-4, heterociclo, heterociclo-alquilo C1-4 y heterociclo-alquenilo C2-4, restos todos que pueden estar opcional e independientemente sustituidos de 1 a 3 veces con un sustituyente seleccionado del grupo que consiste en halogeno, nitro, alquilo C1-4 halosustituido, alquilo C1-4, amino, amina mono- o di-sustituida con alquilo C1-4, ORa, C(O)Ra, NRaC(O)ORa, OC(O)NR6R7, hidroxilo, NR9C(O)Ra, S(O)m'Ra, C(O)NR6R7, C(O)OH, C(O)ORa, S(O)2NR6R7, y NHS(O)2Ra; o los dos sustituyentes Rb están unidos para formar un anillo de 3-10 miembros opcionalmente sustituido y que contiene independientemente, además de carbono, de 1 a 3 restos seleccionados del grupo que consiste en NRa, O, S, SO y SO2, y en el que el sustituyente puede estar opcionalmente insaturado; Ra es seleccionado del grupo que consiste en los restos alquilo, arilo, aril-alquilo C1-4, heteroarilo, heteroaril-alquilo C1-4, heterociclo, COOR13, y heterociclo-alquilo C1-4, todos los cuales pueden estar opcionalmente sustituidos; m es un numero entero que tiene un valor de 1 a 3; m' es 0 o un numero entero que tiene un valor de 1 o 2; n es un numero entero que tiene un valor de 1 a 3; q es 0 o un numero entero que tiene un valor de 1 a 10; t es 0 o un numero entero que tiene un valor de 1 o 2; s es un numero entero que tiene un valor de 1 a 3; R1 es independientemente seleccionado del grupo que consiste en hidrogeno, halogeno, nitro, ciano, alquilo C1-10, alquilo C1-10 halosustituido, alquenilo C2-10, alcoxilo C1-10, alcoxilo C1-10 halosustituido, azida, S(O)tR4, (CR8R8)qS(O)tR4, hidroxilo, alquilo C1-4 sustituido con hidroxilo, arilo, aril-alquilo C1-4, aril-alquenilo C2-10, ariloxilo, aril-alquiloxilo C1-4, heteroarilo, heteroarilalquilo, heteroaril-alquenilo C2-10, heteroaril-alquiloxilo C1-4, heterociclo, heterociclo-alquilo C1-4, heterociclo-alquiloxilo C1-4, heterociclo-alquenilo C2-10, (CR8R8)qNR4R5, (CR8R8)qC(O)NR4R5, alquenil C2-10-C(O)NR4R5, (CR8R8)qC(O)NR4R5, S(O)3R8, (CR8R8)qC(O)R11, alquenil C2-10-C(O)R11, alquenil C2-10-C(O)OR11, (CR8R8)qC(O)OR11, (CR8R8)qOC(O)R11, (CR8R8)qNR4C(O)R11, (CR8R8)qC(NR4)NR4R5, (CR8R8)qNR4C(NR5)R11, (CR8R8)qNHS(O)2R13, y (CR8R8)qS(O)2NR4R5; o dos restos R1 pueden formar conjuntamente O-(CH2)sO o un anillo saturado o insaturado de 5 a 6 miembros, pudiendo estar opcionalmente sustituidos los restos alquilo, arilo, arilalquilo, heteroarilo y heterociclo; R4 y R5 son independientemente seleccionados del grupo que consiste en hidrogeno, alquilo C1-4 opcionalmente sustituido, arilo opcionalmente sustituido, aril-alquilo C1-4 opcionalmente sustituido, heteroarilo opcionalmente sustituido, heteroaril-alquilo C1-4 opcionalmente sustituido, heterociclo, y heterociclo-alquilo C1-4; o R4 y R5 junto con el nitrogeno al que están unidos forman un anillo de 5 a 7 miembros que puede comprender opcionalmente un heteroátomo adicional seleccionado entre O, N y S; R6 y R7 son independientemente seleccionados del grupo que consiste en hidrogeno, alquilo C1-4, heteroarilo, arilo, alquilarilo, y alquil-heteroalquilo C1-4; o R6 y R7 junto con el nitrogeno al que están unidos forman un anillo de 5 a 7 miembros, anillo que puede contener opcionalmente un heteroátomo adicional seleccionado entre oxígeno, nitrogeno y azufre que puede estar opcionalmente sustituido; Y es seleccionado del grupo que consiste en CR14R15, NR14, O, CO, y S(O)t; R8 es hidrogeno o alquilo C1-4; R9 es alquilo C1-4; R10 es alquil C1-10-C(O)2R8; R11es seleccionado del grupo que consiste en hidrogeno, alquilo C1-4 opcionalmente sustituido, arilo opcionalmente sustituido, aril-alquilo C1-4 opcionalmente sustituido, heteroarilo opcionalmente sustituido, heteroaril-alquilo C1-4 opcionalmente sustituido, heterociclo opcionalmente sustituido, y heterociclo-alquilo C1-4 opcionalmente sustituido; R12 es seleccionado del grupo que consiste en hidrogeno, alquilo C1-4, arilo, aril-alquilo C1-4, heteroarilo, heteroaril-alquilo C1-4, heterociclo, y heterociclo-alquilo C1-4; R13 es seleccionado del grupo que consiste en alquilo C1-4, arilo, aril-alquilo C1-4, heteroarilo, heteroaril-alquilo C1-4, heterociclo, y heterociclo-alquilo C1-4; y R14 y R15 son independientemente seleccionados del grupo que consiste en hidrogeno, alquilo C1-4 opcionalmente sustituido, ORa, y NR4R5; o R14 y R15 junto con el(los) átomo(s) al(a los) que están unidos pueden formar un anillo de 4 a 7 miembros que puede contener opcionalmente un heteroátomo adicional que es seleccionado del grupo que consiste en oxígeno, nitrogeno y azufre, anillo que puede estar opcionalmente sustituido. Composiciones farmacéuticas que comprenden estos compuestos y el uso de estos en la fabricacion de medicamentos. Los mencionados compuestos son utiles en el tratamiento de estados morbosos mediados por la interleuquina 8 (IL 8).Sulfonamide-substituted hydroxyphenyl urea compounds of formula (1) or pharmaceutically acceptable salts thereof, wherein: Rb is independently selected from the group consisting of hydrogen, NR6R7, OH, ORa, C1-5 alkyl, aryl, aryl- C1-4 alkyl, C2-4 aryl-alkenyl, cycloalkyl, C1-5 cycloalkyl-alkyl, heteroaryl, heteroaryl-C1-4alkyl, heteroaryl-C2-4alkyl, heterocycle, heterocycle-C1-4alkyl and heterocyclo-alkenyl -4, all moieties which may be optionally and independently substituted 1 to 3 times with a substituent selected from the group consisting of halogen, nitro, halosubstituted C1-4 alkyl, C1-4 alkyl, amino, mono- or di-substituted amine with C1-4 alkyl, ORa, C (O) Ra, NRaC (O) ORa, OC (O) NR6R7, hydroxyl, NR9C (O) Ra, S (O) m'Ra, C (O) NR6R7, C ( O) OH, C (O) ORa, S (O) 2NR6R7, and NHS (O) 2Ra; or the two Rb substituents are joined to form an optionally substituted 3-10 membered ring and independently containing, in addition to carbon, 1 to 3 moieties selected from the group consisting of NRa, O, S, SO and SO2, and in which the substituent may be optionally unsaturated; Ra is selected from the group consisting of the alkyl, aryl, aryl-C1-4 alkyl, heteroaryl, heteroaryl-C1-4 alkyl, heterocycle, COOR13, and heterocycle-C1-4 alkyl moieties, all of which may be optionally substituted; m is an integer that has a value of 1 to 3; m 'is 0 or an integer that has a value of 1 or 2; n is an integer that has a value of 1 to 3; q is 0 or an integer that has a value from 1 to 10; t is 0 or an integer that has a value of 1 or 2; s is an integer that has a value of 1 to 3; R1 is independently selected from the group consisting of hydrogen, halogen, nitro, cyano, C1-10 alkyl, halosubstituted C1-10 alkyl, C2-10 alkenyl, C1-10 alkoxy, halosubstituted C1-10 alkoxy, azide, S (O) tR4, (CR8R8) qS (O) tR4, hydroxy, C1-4 alkyl substituted with hydroxyl, aryl, arylC 1-4 alkyl, arylC2-10 aryl-alkenyl, aryloxy, arylC 1-4 alkyloxy, heteroaryl, heteroarylalkyl, C2-10 heteroaryl-alkenyl, C1-4 heteroaryl-alkyloxy, heterocycle, C1-4 heterocycle-alkyl, C1-4 heterocycle-alkyloxy, C2-10 heterocycle-alkenyl, (CR8R8) qNR4R5, (CR8R8) qC (O) NR4R5 , C2-10-C (O) NR4R5, (CR8R8) qC (O) NR4R5, S (O) 3R8, (CR8R8) qC (O) R11, C2-10-C (O) R11 alkenyl, C2- alkenyl 10-C (O) OR11, (CR8R8) qC (O) OR11, (CR8R8) qOC (O) R11, (CR8R8) qNR4C (O) R11, (CR8R8) qC (NR4) NR4R5, (CR8R8) qNR4C (NR5 ) R11, (CR8R8) qNHS (O) 2R13, and (CR8R8) qS (O) 2NR4R5; or two R1 moieties can together form O- (CH2) sO or a saturated or unsaturated ring of 5 to 6 members, the alkyl, aryl, arylalkyl, heteroaryl and heterocycle moieties being optionally substituted; R4 and R5 are independently selected from the group consisting of hydrogen, optionally substituted C1-4 alkyl, optionally substituted aryl, optionally substituted aryl-C1-4 alkyl, optionally substituted heteroaryl, optionally substituted heteroaryl-C1-4 alkyl, heterocycle, and heterocycle -C1-4 alkyl; or R4 and R5 together with the nitrogen to which they are attached form a 5 to 7 member ring which may optionally comprise an additional heteroatom selected from O, N and S; R6 and R7 are independently selected from the group consisting of hydrogen, C1-4 alkyl, heteroaryl, aryl, alkylaryl, and C1-4 alkyl heteroalkyl; or R6 and R7 together with the nitrogen to which they are attached form a 5- to 7-membered ring, which ring may optionally contain an additional heteroatom selected from oxygen, nitrogen and sulfur which may be optionally substituted; Y is selected from the group consisting of CR14R15, NR14, O, CO, and S (O) t; R8 is hydrogen or C1-4 alkyl; R9 is C1-4 alkyl; R10 is C1-10-C (O) 2R8 alkyl; R11 is selected from the group consisting of hydrogen, optionally substituted C1-4 alkyl, optionally substituted aryl, optionally substituted aryl-C1-4 alkyl, optionally substituted heteroaryl, optionally substituted heteroaryl-C1-4 alkyl, optionally substituted heterocycle, and heterocycle-alkyl C1-4 optionally substituted; R12 is selected from the group consisting of hydrogen, C1-4 alkyl, aryl, aryl-C1-4 alkyl, heteroaryl, heteroaryl-C1-4 alkyl, heterocycle, and heterocycle-C1-4 alkyl; R13 is selected from the group consisting of C1-4 alkyl, aryl, aryl-C1-4 alkyl, heteroaryl, heteroaryl-C1-4 alkyl, heterocycle, and heterocycle-C1-4 alkyl; and R14 and R15 are independently selected from the group consisting of hydrogen, optionally substituted C1-4 alkyl, ORa, and NR4R5; or R14 and R15 together with the atom (s) to which they are attached can form a 4- to 7-membered ring that may optionally contain an additional heteroatom that is selected from the group consisting of oxygen, nitrogen and sulfur, ring that can be optionally substituted. Pharmaceutical compositions comprising these compounds and their use in the manufacture of medicines. The aforementioned compounds are useful in the treatment of morbid conditions mediated by interleukin 8 (IL 8).

ARP010101183A 2000-03-16 2001-03-14 HYDROXIFENIL UREA COMPOUNDS REPLACED WITH SULFONAMIDS, PHARMACEUTICAL COMPOSITIONS THAT INCLUDE THEM, AND USE OF THE SAME IN THE MANUFACTURE OF MEDICINES TO TREAT A DISEASE MEDIATED BY A CHEMIOQUINE AR031098A1 (en)

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