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AR037458A1 - A COMPOSITE DERIVED FROM PIPERIDINE, ITS EMPLOYMENT, METHODS TO PREPARE IT AND A COMPOSITION CONTAINING IT - Google Patents

A COMPOSITE DERIVED FROM PIPERIDINE, ITS EMPLOYMENT, METHODS TO PREPARE IT AND A COMPOSITION CONTAINING IT

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Publication number
AR037458A1
AR037458A1 ARP020104581A ARP020104581A AR037458A1 AR 037458 A1 AR037458 A1 AR 037458A1 AR P020104581 A ARP020104581 A AR P020104581A AR P020104581 A ARP020104581 A AR P020104581A AR 037458 A1 AR037458 A1 AR 037458A1
Authority
AR
Argentina
Prior art keywords
alkyl
hydrogen
amino
cycloalkyl
dialkyl
Prior art date
Application number
ARP020104581A
Other languages
Spanish (es)
Inventor
Bois Daisy Joe Du
Denis John Kertesz
Eric Brian Sjogren
David Bernard Smith
Bei Michelle Wang
Original Assignee
Hoffmann La Roche
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Filing date
Publication date
Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche
Publication of AR037458A1 publication Critical patent/AR037458A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
    • 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
    • C07D401/04—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 directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—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
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pulmonology (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

Un compuesto derivado de piperidina de fórmula (1) en la cual: R1 es alquileno C1-2; R2 es fenilo opcionalmente substituido; R3 es hidrógeno, alquilo C1-6, acilo, arilo o aril-alquilo C1-6; el anillo A es cicloalquilo C3-7, heterociclilo, o fenilo opcionalmente substituido; L es -C(=O)-, -C(=S)-, -SO2-, -C(=O)N(Ra)-, -C(=S)N(Ra)-, -SO2N(Ra)-, -C(=O)O-, -C(=S)O-, -S(=O)2O-, donde Ra es hidrógeno, alquilo C1-6, acilo, arilo, aril-alquilo C1-6, alcoxicarbonilo C1-6 o benciloxicarbonilo; X está ausente, es -(CR'R'')O-, (CR'R'')S-, -(CR'R'')NRb- o alquileno C1-6 donde R' y R'' son independientemente hidrógeno o alquilo C1-6 y Rb es hidrógeno o alquilo C1-6; R4 es arilo o heteroarilo; y R5 es hidrógeno o alquilo C1-6; siempre que cuando R1 es -CH2-, R2 es fenilo, R3 es hidrógeno, R5 es hidrógeno, A es fenilo, L es -C(=O)NH- y X está ausente, entonces R4 no es 2,5-difluorfenilo, o profármacos, isómeros individuales, mezclas racémicas y no racémicas de isómeros, y sales farmacéuticamente aceptables de los mismos; donde: la frase "fenilo opcionalmente substituido" se refiere a un grupo fenilo que está opcionalmente substituido por uno o más sustituyentes seleccionados entre el grupo que comprende alquilo C1-6, haloalquilo C1-6 hidroxialquilo C1-6, heteroalquilo, acilo, acilamino, amino, alquil C1-6amino, dialquil C1-6amino, alquil C1-6tio, alquil C1-6sulfinilo, alquil C1-6sulfonilo, -SO2NR'R'' (donde R' y R'' son independientemente hidrógeno o alquilo C1-6), alcoxi C1-6, haloalcoxi C1-6, alcoxi C1-6carbonilo, carbamoilo, hidroxi, halo nitro, ciano, mercapto, metilendioxi o etilendioxi; el término "acilo" significa un radical -C(O)R, en el cual R es hidrógeno, alquilo C1-6, cicloalquilo C3-7, cicloalquil C3-7-alquilo C1-6, fenilo o fenilalquilo C1-6; el término "arilo" se refiere a un radical de hidrocarburo aromático monocíclico o bicíclico, que tiene entre 6 y 10 átomos en el anillo, que está opcionalmente substituido por uno o más sustituyentes seleccionados entre el grupo que comprende alquilo C1-6, haloalquilo C1-6, hidroxialquilo C1-6, heteroalquilo, acilo, acilamino, amino, alquil C1-6amino, dialquil C1-6amino, alquil C1-6tio, alquil C1-6sulfinilo, alquil C1-6sulfonilo, -SO2NR'R'' (donde R' y R'' son independientemente hidrógeno o alquilo C1-6), alcoxi C1-6, haloalcoxi C1-6, alcoxi C1-6carbonilo, carbamoilo, hidroxi, halo, nitro, ciano, mercapto, metilendioxi o etilendioxi; el término "heteroarilo" se refiere a un radical monocíclico o bicíclico que tiene entre 5 y 12 átomos en el anillo, que tiene al menos un anillo aromático que contiene uno, dos o tres heteroátomos en el anillo seleccionados entre N, O ó S, el resto de los átomos del anillo son C, entendiendo que el punto de unión del radical heteroarilo será en un anillo aromático, y el anillo heteroarilo está opcionalmente substituido en forma independiente por uno o más sustituyentes seleccionados entre alquilo C1-6, haloalquilo C1-6, hidroxialquilo C1-6, heteroalquilo, acilo, acilamino, amino, alquil C1-6amino, dialquil C1-6amino, alquil C1-6tio, alquil C1-6sulfinilo, alquil C1-6sulfonilo, -SO2NR'R'' (donde R' y R'' son independientemente hidrógeno o alquilo C1-6), alcoxi C1-6, haloalcoxi C1-6, alcoxi C1-6carbonilo, carbamoilo, hidroxi, halo, nitro, ciano, mercapto, metilendioxi, etilendioxi, o fenilo opcionalmente substituido; el término "heteroalquilo" se refiere a un radical alquilo C1-6 en el cual uno, dos o tres átomos de hidrógeno se reemplazaron por un substituyente independientemente seleccionado entre el grupo que comprende -ORa, -NRbRc, y -S(O)nRd (donde n es un entero que oscila entre 0 y 2), entendiendo que el punto de unión del radical heteroalquilo es a través de un átomo de carbono, donde Ra es hidrógeno, acilo, alquilo C1-6, cicloalquilo C3-7 o cicloalquil C3-7-alquilo C1-6; Rb y Rc son independientemente uno del otro hidrógeno, acilo, alquilo C1-6, cicloalquilo C3-7 o cicloalquil C3-7-alquilo C1-6; cuando n es 0, Rd es hidrógeno, alquilo C1-6, cicloalquilo C3-7 o cicloalquil C3-7-alquilo C1-6 y cuando n es 1 o 2, Rd es alquilo C1-6, cicloalquilo C3-7, cicloalquil C3-7-alquilo C1-6, amino, acilamino, monoalquil C1-6amino o dialquil C1-6amino; el término "heterociclilo" se refiere a un radical cíclico no aromático saturado o insaturado que tiene entre 3 y 8 átomos en el anillo, donde uno o dos átomos del anillo son heteroátomos seleccionados entre NRx (donde cada Rx es independientemente hidrógeno, alquilo C1-6, acilo, alquil C1-6sulfonilo, aminosulfonilo, (alquil C1-6amino)sulfonilo, (dialquil C1-6amino)sulfonilo, carbamoilo, (alquil C1-6amino)carbonilo, (dialquil C1-6amino)carbonilo, (carbonil)alquilo C1-6, (alquil C1-6amino)carbonilalquilo C1-6, o dialquil C1-6aminocarbonilalquilo C1-6, O, o S(O)n (donde n es un entero que oscila entre 0 y 2) el resto de los átomos del anillo son C, y el anillo heterociclilo puede estar opcionalmente substituido en forma independiente por uno, dos o tres sustituyentes seleccionados entre alquilo C1-6, haloalquilo C1-6, heteroalquilo, halo, nitro, cianoalquilo C1-6, hidroxi, alcoxi C1-6amino, monoalquil C1-6amino, dialquil C1-6amino, arilalquilo C1-6, (X)n-C(O)R (donde X es O ó NR', n es 0 ó 1, R es hidrógeno, alquilo C1-6, haloalquilo C1-6, hidroxi, alcoxi C1-6, amino, monoalquil C1-6amino, dialquil C1-6amino o fenilo opcionalmente substituido, y R' es hidrógeno o alquilo C1-6, -alquilenoC1-6-C(O)R (donde R es hidrógeno, alquilo C1-6, haloalquilo C1-6, hidroxi, alcoxi C1-6, amino, monoalquil C1-6amino, dialquil C1-6amino o fenilo opcionalmente substituido), o S(O)nRd (donde n es un entero que oscila entre 0 y 2 , y Rd es hidrógeno (siempre y cuando n sea 0), alquilo C1-6, haloalquilo C1-6, cicloalquilo C3-7, cicloalquil C3-7-alquilo C1-6, amino, monoalquil C1-6amino, dialquil C1-6amino, o hidroxialquilo C1-6. Su empleo, métodos para su preparación y una composición que lo contiene. El compuesto de fórmula (1) es útil como antagonista del receptor CCR-3 y, por lo tanto, puede utilizarse en el tratamiento de enfermedades mediadas por CCR-3, como el asma.A compound derived from piperidine of formula (1) in which: R1 is C1-2 alkylene; R2 is optionally substituted phenyl; R3 is hydrogen, C1-6 alkyl, acyl, aryl or aryl-C1-6 alkyl; Ring A is C3-7 cycloalkyl, heterocyclyl, or optionally substituted phenyl; L is -C (= O) -, -C (= S) -, -SO2-, -C (= O) N (Ra) -, -C (= S) N (Ra) -, -SO2N (Ra ) -, -C (= O) O-, -C (= S) O-, -S (= O) 2O-, where Ra is hydrogen, C1-6 alkyl, acyl, aryl, aryl-C1-6 alkyl , C1-6 alkoxycarbonyl or benzyloxycarbonyl; X is absent, it is - (CR'R '') O-, (CR'R '') S-, - (CR'R '') NRb- or C1-6 alkylene where R 'and R' 'are independently hydrogen or C1-6 alkyl and Rb is hydrogen or C1-6 alkyl; R4 is aryl or heteroaryl; and R5 is hydrogen or C1-6 alkyl; provided that when R1 is -CH2-, R2 is phenyl, R3 is hydrogen, R5 is hydrogen, A is phenyl, L is -C (= O) NH- and X is absent, then R4 is not 2,5-difluorphenyl, or prodrugs, individual isomers, racemic and non-racemic mixtures of isomers, and pharmaceutically acceptable salts thereof; where: the phrase "optionally substituted phenyl" refers to a phenyl group that is optionally substituted by one or more substituents selected from the group comprising C1-6 alkyl, C1-6 haloalkyl C1-6 hydroxyalkyl, heteroalkyl, acyl, acylamino, amino, C1-6 alkyl, C1-6 dialkyl, C1-6thio alkyl, C1-6sulfinyl alkyl, C1-6 sulfonyl alkyl, -SO2NR'R '' (where R 'and R' 'are independently hydrogen or C1-6 alkyl) , C1-6 alkoxy, C1-6 haloalkoxy, C1-6 alkoxycarbonyl, carbamoyl, hydroxy, halo nitro, cyano, mercapto, methylenedioxy or ethylenedioxy; the term "acyl" means a radical -C (O) R, in which R is hydrogen, C 1-6 alkyl, C 3-7 cycloalkyl, C 3-7 cycloalkyl-C 1-6 alkyl, phenyl or C 1-6 phenylalkyl; The term "aryl" refers to a monocyclic or bicyclic aromatic hydrocarbon radical, having between 6 and 10 ring atoms, which is optionally substituted by one or more substituents selected from the group comprising C1-6 alkyl, C1 haloalkyl -6, C1-6 hydroxyalkyl, heteroalkyl, acyl, acylamino, amino, C1-6 amino alkyl, C1-6 amino dialkyl, C1-6thio alkyl, C1-6sulfinyl alkyl, C1-6sulfonyl alkyl, -SO2NR'R '' (where R 'and R' 'are independently hydrogen or C 1-6 alkyl), C 1-6 alkoxy, C 1-6 haloalkoxy, C 1-6 alkoxycarbonyl, carbamoyl, hydroxy, halo, nitro, cyano, mercapto, methylenedioxy or ethylenedioxy; the term "heteroaryl" refers to a monocyclic or bicyclic radical having between 5 and 12 ring atoms, which has at least one aromatic ring containing one, two or three ring heteroatoms selected from N, O or S, the rest of the ring atoms are C, understanding that the point of attachment of the heteroaryl radical will be in an aromatic ring, and the heteroaryl ring is optionally independently substituted by one or more substituents selected from C1-6 alkyl, C1- haloalkyl 6, C1-6 hydroxyalkyl, heteroalkyl, acyl, acylamino, amino, C1-6 amino alkyl, C1-6 alkyl dialino, C1-6thio alkyl, C1-6sulfinyl alkyl, C1-6sulfonyl alkyl, -SO2NR'R '' (where R ' and R '' are independently hydrogen or C 1-6 alkyl), C 1-6 alkoxy, C 1-6 haloalkoxy, C 1-6 alkoxycarbonyl, carbamoyl, hydroxy, halo, nitro, cyano, mercapto, methylenedioxy, ethylenedioxy, or optionally substituted phenyl; the term "heteroalkyl" refers to a C1-6 alkyl radical in which one, two or three hydrogen atoms were replaced by a substituent independently selected from the group comprising -ORa, -NRbRc, and -S (O) nRd (where n is an integer ranging from 0 to 2), understanding that the point of attachment of the heteroalkyl radical is through a carbon atom, where Ra is hydrogen, acyl, C1-6 alkyl, C3-7 cycloalkyl or cycloalkyl C3-7-C1-6 alkyl; Rb and Rc are independently of each other hydrogen, acyl, C1-6 alkyl, C3-7 cycloalkyl or C3-7 cycloalkyl-C1-6 alkyl; when n is 0, Rd is hydrogen, C1-6 alkyl, C3-7 cycloalkyl or C3-7 cycloalkyl-C1-6 alkyl and when n is 1 or 2, Rd is C1-6 alkyl, C3-7 cycloalkyl, C3 cycloalkyl -7-C1-6 alkyl, amino, acylamino, C1-6amino monoalkyl or C1-6amino dialkyl; The term "heterocyclyl" refers to a saturated or unsaturated non-aromatic cyclic radical having between 3 and 8 ring atoms, where one or two ring atoms are heteroatoms selected from NRx (where each Rx is independently hydrogen, C1- alkyl) 6, acyl, C1-6 alkyl sulfonyl, aminosulfonyl, (C1-6 amino alkyl) sulfonyl, (dialkyl C1-6 amino) sulfonyl, carbamoyl, (C1-6 amino alkyl) carbonyl, (dialkyl C1-6 amino) carbonyl, (carbonyl) C1 alkyl -6, (C1-6 alkyl) carbonyl C1-6 alkyl, or C1-6 dialkyl C1-6 aminocarbonylalkyl, O, or S (O) n (where n is an integer ranging from 0 to 2) the rest of the atoms of the ring are C, and the heterocyclyl ring may be optionally substituted independently by one, two or three substituents selected from C1-6 alkyl, C1-6 haloalkyl, heteroalkyl, halo, nitro, C1-6 cyanoalkyl, hydroxy, C1- alkoxy 6amino, C1-6amino monoalkyl, C1-6amino dialkyl, C1-6 arylalkyl, (X) nC (O) R (where X is O or NR ', n is 0 or 1, R is hydrogen, C 1-6 alkyl, C 1-6 haloalkyl, hydroxy, C 1-6 alkoxy, amino, C 1-6 aminoalkyl, C 1-6 dialkyl or optionally substituted phenyl, and R' is hydrogen or C1-6 alkyl, C1-6-C-alkylene (O) R (where R is hydrogen, C1-6 alkyl, C1-6 haloalkyl, hydroxy, C1-6 alkoxy, amino, C1-6 amino monoalkyl, C1-6 amino dialkyl or optionally substituted phenyl), or S (O) nRd (where n is an integer ranging from 0 to 2, and Rd is hydrogen (as long as n is 0), C1-6 alkyl, C1-6 haloalkyl, C3 cycloalkyl -7, C 3-7 cycloalkyl-C 1-6 alkyl, amino, C 1-6 aminoalkyl, C 1-6 dialkyl, or C 1-6 hydroxyalkyl. Its use, methods for its preparation and a composition that contains it. The compound of formula (1) is useful as a CCR-3 receptor antagonist and, therefore, can be used in the treatment of diseases mediated by CCR-3, such as asthma.

ARP020104581A 2001-11-30 2002-11-28 A COMPOSITE DERIVED FROM PIPERIDINE, ITS EMPLOYMENT, METHODS TO PREPARE IT AND A COMPOSITION CONTAINING IT AR037458A1 (en)

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KR (1) KR100652450B1 (en)
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EP1558599A4 (en) * 2002-10-30 2007-06-27 Merck & Co Inc HETEROARYLPIPERIDINE MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY
IN2006CH00378A (en) * 2003-06-30 2007-05-11 Sumitomo Chemical Co Asymmetric urea compound and process for producing asymmetric compound by asymmetric conjugate addition reaction with the same as catalyst
WO2005058805A1 (en) * 2003-12-17 2005-06-30 Sumitomo Chemical Company, Limited Process for producing optically active amine compound
WO2006071875A1 (en) 2004-12-29 2006-07-06 Millennium Pharmaceuticals, Inc. Compounds useful as chemokine receptor antagonists
US7635698B2 (en) 2004-12-29 2009-12-22 Millennium Pharmaceuticals, Inc. Compounds useful as chemokine receptor antagonists
EP2805985A1 (en) * 2013-05-22 2014-11-26 Sika Technology AG Polymer containing hydroxysilane and silane groups

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US6444686B1 (en) * 1998-12-18 2002-09-03 Brsitol-Myers Squibb Pharma Company N-ureidoalkyl-piperidines as modulators of chemokine receptor activity

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RU2004120064A (en) 2006-01-10
EP1453825A1 (en) 2004-09-08
JP2005515193A (en) 2005-05-26
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