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WO1999038514A1 - Amines cycliques utilisees en tant que modulateurs de l'activite du recepteur de chemokine - Google Patents

Amines cycliques utilisees en tant que modulateurs de l'activite du recepteur de chemokine Download PDF

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Publication number
WO1999038514A1
WO1999038514A1 PCT/US1999/002165 US9902165W WO9938514A1 WO 1999038514 A1 WO1999038514 A1 WO 1999038514A1 US 9902165 W US9902165 W US 9902165W WO 9938514 A1 WO9938514 A1 WO 9938514A1
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WIPO (PCT)
Prior art keywords
alkyl
substituted
phenyl
hydroxy
substituents
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/US1999/002165
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English (en)
Inventor
Charles G. Caldwell
Paul E. Finke
Malcolm Maccoss
Sander G. Mills
Bryan Oates
Dooseop Kim
Shankaran Kothandaraman
Liping Wang
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck and Co Inc
Original Assignee
Merck and Co Inc
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
Priority claimed from GBGB9810890.5A external-priority patent/GB9810890D0/en
Application filed by Merck and Co Inc filed Critical Merck and Co Inc
Priority to JP2000529247A priority Critical patent/JP2002501898A/ja
Priority to CA002319781A priority patent/CA2319781A1/fr
Priority to AU26543/99A priority patent/AU2654399A/en
Priority to EP99906697A priority patent/EP1052992A1/fr
Publication of WO1999038514A1 publication Critical patent/WO1999038514A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/18—Antivirals for RNA viruses for HIV
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/04—Immunostimulants
    • 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
    • C07D211/36—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 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
    • C07D211/56—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • C07D401/06—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 only aliphatic carbon atoms
    • 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
    • C07D405/06—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 linked by a carbon chain containing only aliphatic carbon atoms
    • 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
    • C07D409/06—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 carbon chain containing only aliphatic carbon atoms

Definitions

  • Chemokines are chemotactic cytokines that are released by a wide variety of cells to attract macrophages, T cells, eosinophils, basophils and neutrophils to sites of inflammation (reviewed in Schall, Cvtokine. 3, 165-183 (1991) and Murphy, Rev. Immun.. 12, 593-633 (1994)).
  • ⁇ -chemokines such as interleukin-8 (IL-8), neutrophil-activating protein-2 (NAP-2) and melanoma growth stimulatory activity protein (MGSA) are chemotactic primarily for neutrophils, whereas ⁇ -chemokines, such as RANTES, MlP-l ⁇ , MIP- l ⁇ , monocyte chemotactic protein-1 (MCP-1), MCP-2, MCP-3 and eotaxin are chemotactic for macrophages, T-cells, eosinophils and basophils (Deng, et al., Nature. 381. 661-666 (1996)).
  • IL-8 interleukin-8
  • NAP-2 neutrophil-activating protein-2
  • MGSA melanoma growth stimulatory activity protein
  • chemokines bind specific cell-surface receptors belonging to the family of G-protein-coupled seven-transmembrane- domain proteins (reviewed in Horuk, Trends Pharm. Sci.. 15. 159-165 (1994)) which are termed "chemokine receptors.” On binding their cognate ligands, chemokine receptors transduce an intracellular signal though the associated trimeric G protein, resulting in a rapid increase in intracellular calcium concentration.
  • CCR-1 or "CKR-1" or "CC-CKR-1”
  • MlP-l ⁇ , MlP-l ⁇ , MCP-3, RANTES a human chemokine receptor that bind or respond to ⁇ -chemokines with the following characteristic pattern: CCR-1 (or "CKR-1" or "CC-CKR-1") [MlP-l ⁇ , MlP-l ⁇ , MCP-3, RANTES] (Ben-Barruch, et al., J. Biol. Chem.. 270.
  • the ⁇ -chemokines include eotaxin, MIP ("macrophage inflammatory protein”), MCP ("monocyte chemoattractant protein”) and RANTES ("regulation-upon-activation, normal T expressed and secreted").
  • Chemokine receptors such as CCR-1, CCR-2, CCR-2A, CCR-2B, CCR-3, CCR-4, CCR-5, CXCR-3, CXCR-4, have been implicated as being important mediators of inflammatory and immunoregulatory disorders and diseases, including asthma and allergic diseases, as well as autoimmune pathologies such as rheumatoid arthritis and atherosclerosis.
  • the chemokine receptor CCR-3 plays a pivotal role in attracting eosinophils to sites of allergic inflammation. Accordingly, agents which modulate chemokine receptors would be useful in such disorders and diseases.
  • HIV-1 human immunodeficiency virus
  • AIDS acute immune deficiency syndrome
  • Certain compounds have been demonstrated to inhibit the replication of HIV, including soluble CD4 protein and synthetic derivatives (Smith, et al., Science. 238. 1704-1707 (1987)), dextran sulfate, the dyes Direct Yellow 50, Evans Blue, and certain azo dyes (U.S. Patent No. 5,468,469). Some of these antiviral agents have been shown to act by blocking the binding of gpl20, the coat protein of HIV, to its target, the CD4 gyycoprotein of the cell.
  • the principal cofactor for entry mediated by the envelope glycoproteins of primary macrophage-trophic strains of HIV-1 is CCR5, a receptor for the ⁇ - chemokines RANTES, MlP-l ⁇ and MlP-l ⁇ (Deng, et al., Nature. 381. 661-666 (1996)). HIV attaches to the CD4 molecule on cells through a region of its envelope protein, gpl20. It is believed that the CD-4 binding site on the gpl20 of HIV interacts with the CD4 molecule on the cell surface, and undergoes conformational changes which allow it to bind to another cell-surface receptor, such as CCR5 and/or CXCR-4.
  • Macrophage-tropic H-TV and SIV envelope proteins have been shown to induce a signal through CCR-5 on CD4+ cells resulting in chemotaxis of T cells which may enhance the replication of the virus (Weissman, et al., Nature. 389. 981-985 (1997)). It has been shown that ⁇ - chemokine ligands prevent HIV-1 from fusing with the cell (Dragic, et al., Nature. 381. 667-673 (1996)).
  • chemokine receptors may be used by some strains of HIV-l or may be favored by non-sexual routes of transmission. Although most HIV-l isolates studied to date utilize CCR-5 or fusin, some can use both as well as the related CCR-2B and CCR-3 as co-receptors (Nature Medicine. 2(11), 1240-1243 (1996)). Nevertheless, drugs targeting chemokine receptors may not be unduly compromised by the genetic diversity of HIV-l (Zhang, et al., Nature. 383. 768 (1996)). The ⁇ -chemokine macrophage-derived chemokine (MDC) has been shown to inhibit HIV-l infection (Pal, et al., Science. 278 (5338), 695-698 (1997).
  • MDC ⁇ -chemokine macrophage-derived chemokine
  • chemokines RANTES, MlP-l ⁇ , MlP-l ⁇ , vMIP-I, vMIP-II, SDF-1 have also been shown to suppress HIV.
  • a derivative of RANTES, (AOP)-RANTES is a subnanomolar antagonist of CCR-5 function in monocytes (Simmons, et al., Science. 276. 276-279 (1997)).
  • Monoclonal antibodies to CCR-5 have been reported to block infection of cells by HIV in vitro. Accordingly, an agent which could block chemokine receptors in humans who possess normal chemokine receptors should prevent infection in healthy individuals and slow or halt viral progression in infected patients (see Science. 275. 1261-1264 (1997)).
  • peptides eotaxin, RANTES, MlP-l ⁇ , MlP-l ⁇ , MCP-1, and MCP-3 are known to bind to chemokine receptors.
  • the inhibitors of HIV-l replication present in supernatants of CD8+ T cells have been characterized as the ⁇ -chemokines RANTES, MlP-l ⁇ and MlP-l ⁇ .
  • PCT Patent Publication WO 97/10211 and EPO Patent Publication EP 0,673,928 disclose certain piperidines as tachykinin antagonists.
  • PCT Patent Publications WO 97/24325 and WO 97/44329, and Japan Patent Publication JP 09,249,566 disclose certain compounds as chemokine antagonists.
  • the present invention is directed to compounds which are modulators of chemokine receptor activity and are useful in the prevention or treatment of certain inflammatory and immunoregulatory
  • the invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which chemokine receptors are involved.
  • the present invention is further concerned with compounds which inhibit the entry of human immunodeficiency virus (HIV) into target cells and are of value in the prevention of infection by HIV, the treatment of infection by HIV and the prevention and/or treatment of the resulting acquired immune deficiency syndrome (AIDS).
  • HIV human immunodeficiency virus
  • the present invention also relates to pharmaceutical compositions containing the compounds and to a method of use of the present compounds and other agents for the prevention and treatment of AIDS and viral infection by HIV.
  • the present invention is directed to compounds of formula I:
  • Rl is selected from a group consisting of: linear or branched Ci_8 alkyl, linear or branched C2-8 alkenyl, wherein the Ci-8 alkyl or C2-8 alkenyl is optionally mono, di, tri or tetra substituted, where the substituents are independently selected from: (a) hydroxy, (b) oxo,
  • halogen which is selected from F, Cl, Br, and I,
  • heteroaryl wherein heteroaryl is selected from the group consisting of: (l 1 ) benzimidazolyl,
  • Ci-6 alkyl J (4) substituted Cl-6 alkyl, where the substituents are independently selected from:
  • R 4 and R 5 are independently selected from hydrogen, Cl-6 alkyl, and Cl-6 alkyl substituted with C5-8 cycloalkyl, (g) -N(R 4 )-CO-O-(R 5 ), and (h) -N(R 4 ')-CO-N(R )(R 5 ), wherein R 4 ' is selected from the definitions of R 4 ,
  • R3 is selected from the group consisting of:
  • Ar is selected from the group consisting of:
  • heteroaryl is selected from the group consisting of:
  • heteroaryl group of items (l 1 ) to (37') is unsubstituted, or mono, di or tri-substituted, where the substituents are selected from:
  • R7 is selected from the group consisting of:
  • R 6 and R7 may be joined together to form a 5-, 6-, or 7- membered monocyclic saturated ring containing 1 or 2 heteroatoms independently selected from nitrogen, oxygen, and sulfur, and in which the ring is unsubstituted or mono or di-substituted, the substituents independently selected from:
  • R8 is selected from the group consisting of:
  • n is an integer selected from 0, 1 and 2 and pharmaceutically acceptable salts thereof.
  • Preferred compounds of the present invention include those of formula la:
  • Rl is selected from a group consisting of: C3, C4, C5. C ⁇ , C7, or C8 linear or branched alkyl, which is unsubstituted or mono, di or tri-substituted, where the substituents are independently selected from:
  • R7 is Cl-6 alkyl, benzyl or phenyl which is unsubsituted or substituted with halo, CF3, Cl-6alkyl, or Ci_3alkoxy,
  • heteroaryl is selected from the group consisting of:
  • R3 is selected from the group consisting of:
  • Ar is selected from the group consisting of:
  • Ci-io alkyl C2-10 alkenyl or C2-10 alkynyl, where the substituents are independently selected from
  • n is an integer selected from 0, 1 and 2, with the proviso that the sum of m + n is 2; and pharmaceutically acceptable salts thereof.
  • More preferred compounds of the present invention include those of formula Ib:
  • Rl, R2 and R ⁇ are as defined herein; and pharmaceutically acceptable salts thereof.
  • Rl is selected from the group consisting of:
  • C3, C4, C5. C ⁇ , C7, or Cs linear or branched alkyl, which is unsubstituted or mono, di or tri-substituted, where the substituents are independently selected from: (a) hydroxy, (b) Cl or F,
  • heteroaryl is selected from the group consisting of:
  • Rl bears at least one substituent which is selected from:
  • Rl is selected from the group consisting of:
  • R 6 is Cl-3 alkyl, unsubstituted or substituted with cyclohexyl, and R is Cl-6 alkyl, benzyl or phenyl which is unsubsituted or substituted with halo, CF3, Ci-3alkyl, or Ci-3alkoxy,
  • Rl is selected from the group consisting of:
  • Rl is C4 linear alkyl, which is substituted, where the substituents are independently selected from: (a) phenyl,
  • Rl is:
  • B is selected from the group consisting of: (a) phenyl, and (b) di or tri-substituted phenyl, wherein the substituents on phenyl are independently selected from: chloro, methyl, phenyl, Ci-3alkoxy, and CF3;
  • R 6 is Ci-3 alkyl, unsubstituted or substituted with cyclohexyl
  • RlO is selected from the group consisting of:
  • RH and R ⁇ 2 are independently selected from the group consisting of:
  • Rl is selected from the group consisting of:
  • Rl is selected from the group consisting of:
  • R2 is selected from the group consisting of:
  • R2 is selected from the group consisting of:
  • R2 is hydrogen
  • (m) -CH2-heteroaryl, with the heteroaryl is selected from the group consisting of: (10 imidazolyl, (20 oxazolyl,
  • Ar is selected from: phenyl, mono substituted phenyl or di-substituted phenyl, wherein the substituents are selected from the group consisting of:
  • Ar is selected from: phenyl, or mono substituted phenyl wherein the substituent is selected from : -NO2. -CONH2, and -CO2H.
  • Ar is selected from: phenyl, or para-NO2 phenyl.
  • R 3 is:
  • R3 is:
  • R3 is selected from: (1) -N(R 8 )-CO-O-(CH2)-phenyl,
  • R 8 is selected from the group consisting of:
  • Ci-io alkyl C2-10 alkenyl or C2-10 alkynyl, where the substituents are independently selected from:
  • R 8 is selected from the group consisting of: (1) C2-10 alkenyl,
  • Ci-io alkyl C2-IO alkenyl or C2-10 alkynyl, where the substituents are independently selected from: (a) C3-4 cycloalkyl,
  • R 8 is selected from the group consisting of:
  • R 8 is selected from the group consisting of:
  • n is an integer selected from 0, 1 and 2 with the proviso that the sum of m + n is 2.
  • n is 1.
  • halo as used herein are intended to include chloro, fluoro, bromo and iodo.
  • Cl-6, as in Cl-6alkyl is defined to identify the group as having 1, 2, 3, 4, 5, or 6 carbons, such that Cl-6alkyl specifically includes methyl, ethyl, propyl, butyl, pentyl, hexyl, and cyclohexyl.
  • Preferred compounds of the present invention include the compounds of the formula:
  • Specific compounds within the present invention include a compound which selected from the group consisting of:
  • N N o c A N

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  • Veterinary Medicine (AREA)
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  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Virology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Oncology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Communicable Diseases (AREA)
  • AIDS & HIV (AREA)
  • Molecular Biology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

Cette invention concerne des amines cycliques de formule (I). Dans la formule (I), R?1,R2, R3¿, m et n sont tels que dans le descriptif. Ces amines cycliques sont utiles en tant que modulateurs de l'activité du récepteur de chémokine, et de manière plus spécifique elles sont utiles en tant que modulateurs des récepteurs de chémokine CCR-1, CCR-2, CCR-2A, CCR-2B, CCR-3, CCR-4, CCR-5, CXCR-3 et/ou CXCR-4.
PCT/US1999/002165 1998-02-02 1999-02-01 Amines cycliques utilisees en tant que modulateurs de l'activite du recepteur de chemokine Ceased WO1999038514A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
JP2000529247A JP2002501898A (ja) 1998-02-02 1999-02-01 ケモカイン受容体活性の環状アミン調節剤
CA002319781A CA2319781A1 (fr) 1998-02-02 1999-02-01 Amines cycliques utilisees en tant que modulateurs de l'activite du recepteur de chemokine
AU26543/99A AU2654399A (en) 1998-02-02 1999-02-01 Cyclic amine modulators of chemokine receptor activity
EP99906697A EP1052992A1 (fr) 1998-02-02 1999-02-01 Amines cycliques utilisees en tant que modulateurs de l'activite du recepteur de chemokine

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US7344698P 1998-02-02 1998-02-02
US60/073,446 1998-02-02
GB9810890.5 1998-05-20
GBGB9810890.5A GB9810890D0 (en) 1998-05-20 1998-05-20 Cyclic amine modulators of chemokine receptor activity

Publications (1)

Publication Number Publication Date
WO1999038514A1 true WO1999038514A1 (fr) 1999-08-05

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PCT/US1999/002165 Ceased WO1999038514A1 (fr) 1998-02-02 1999-02-01 Amines cycliques utilisees en tant que modulateurs de l'activite du recepteur de chemokine

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EP (1) EP1052992A1 (fr)
JP (1) JP2002501898A (fr)
AU (1) AU2654399A (fr)
CA (1) CA2319781A1 (fr)
WO (1) WO1999038514A1 (fr)

Cited By (51)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000042045A3 (fr) * 1999-01-13 2000-11-09 Warner Lambert Co Heterocycles fonctionnalises en tant que modulateurs des recepteurs de chimiokines
WO2002034745A1 (fr) * 2000-09-15 2002-05-02 Anormed Inc. Composes heterocycliques se liant au recepteur de la chimiokine
WO2002022600A3 (fr) * 2000-09-15 2002-05-10 Anormed Inc Composes heterocycliques se liant avec les recepteurs de chimiokines
WO2002022599A3 (fr) * 2000-09-15 2002-05-30 Anormed Inc Composes heterocycliques se liant avec les recepteurs de chimiokines
US6511826B2 (en) 1995-06-06 2003-01-28 Human Genome Sciences, Inc. Polynucleotides encoding human G-protein chemokine receptor (CCR5) HDGNR10
WO2003018556A1 (fr) * 2001-07-23 2003-03-06 Astrazeneca Ab Derives de piperidine utiles en tant que modulateurs de l'activite des recepteurs de la chimiokine
WO2002079186A3 (fr) * 2001-03-30 2003-05-01 Hoffmann La Roche Derives d'aminopiperidine
US6562978B1 (en) 1999-10-01 2003-05-13 Takeda Chemical Industries, Ltd. Cyclic amine compounds as CCR5 antagonists
JP2003516965A (ja) * 1999-12-14 2003-05-20 ソシエテ・ド・コンセイユ・ド・ルシエルシエ・エ・ダアツプリカーション・シヤンテイフイツク・（エス．セー．エール．アー．エス） ４−アミノピペリジン誘導体及びその医薬としての使用
US6743594B1 (en) 1995-06-06 2004-06-01 Human Genome Sciences, Inc. Methods of screening using human G-protein chemokine receptor HDGNR10 (CCR5)
US6887871B2 (en) 2000-02-23 2005-05-03 Astrazeneca Ab Use of phenylheteroakylamine derivatives
US6900243B2 (en) 2000-02-23 2005-05-31 Astrazeneca Ab Phenylheteroalkylamine derivatives
US6903085B1 (en) 1999-08-24 2005-06-07 Astrazeneca, Ab Substituted piperidine compounds useful as modulators of chemokine receptor activity
WO2005090330A1 (fr) * 2004-03-22 2005-09-29 Astrazeneca Ab Derives de n-piperidine utilises en tant que modulateurs ccr3
US6953797B2 (en) 2000-02-23 2005-10-11 Astrazeneca Ab Use of phenylheteroalkylamine derivatives
WO2005097775A1 (fr) * 2004-04-06 2005-10-20 Astrazeneca Ab Derives de piperidine utilises pour le traitement des maladies induites par les chimiokines
US6958350B2 (en) 2001-02-19 2005-10-25 Astrazeneca Ab Chemical compounds
US6960602B2 (en) 2001-03-22 2005-11-01 Astrazeneca Ab Piperidine derivatives as modulators of chemokine receptors
RU2277092C2 (ru) * 2000-09-15 2006-05-27 Анормед, Инк. Гетероциклические соединения, их применение и фармацевтическая композиция для лечения состояний, опосредованных схсr4 и ccr5
US7144903B2 (en) 2001-05-23 2006-12-05 Amgen Inc. CCR4 antagonists
WO2006129679A1 (fr) 2005-05-31 2006-12-07 Ono Pharmaceutical Co., Ltd. Compose de spiropiperidine et son utilisation medicinale
US7175988B2 (en) 2001-02-09 2007-02-13 Human Genome Sciences, Inc. Human G-protein Chemokine Receptor (CCR5) HDGNR10
US7186718B2 (en) 2001-08-22 2007-03-06 Astrazeneca Ab Piperidinyl-morpholinyl derivatives as modulators of chemokine receptor activity
US7192973B2 (en) 2001-11-15 2007-03-20 Astrazeneca Ab Piperidine derivatives and their use as modulators of chemokine receptor activity (especially CCR5)
RU2297413C2 (ru) * 2000-09-15 2007-04-20 Анормед, Инк. Гетероциклические соединения, моделирующие активность хемокинового рецептора, их применение и содержащая их фармацевтическая композиция
WO2007049771A1 (fr) 2005-10-28 2007-05-03 Ono Pharmaceutical Co., Ltd. Compose contenant un groupe basique et son utilisation
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