CA2413000A1 - Five-membered ring compounds - Google Patents

Five-membered ring compounds Download PDF

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CA2413000A1
CA2413000A1 CA002413000A CA2413000A CA2413000A1 CA 2413000 A1 CA2413000 A1 CA 2413000A1 CA 002413000 A CA002413000 A CA 002413000A CA 2413000 A CA2413000 A CA 2413000A CA 2413000 A1 CA2413000 A1 CA 2413000A1
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substituted
unsubstituted
alkyl
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CA2413000C (en
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Norio Fujiwara
Hitoshi Fujita
Fujio Antoku
Toshinari Sugasawa
Hajime Kawakami
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Sumitomo Pharma Co Ltd
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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
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • 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
    • 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
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • 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
    • A61P37/08—Antiallergic agents
    • 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
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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
    • C07D277/38—Nitrogen atoms
    • C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Immunology (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Pulmonology (AREA)
  • Transplantation (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

The present invention is directed to a 5-membered cyclic compound of the formula:

(see above formula) wherein X is oxygen or sulfur, R1 is hydrogen, substituted or unsubstituted alkyl, etc., R2 is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, etc., Y1 is a direct bond, substituted or unsubstituted alkylene, -CO(CH2)n-, etc., the wavy line means (E)-configuration or (Z)-configuration, R3 is substituted or unsubstituted aryl, etc., Y2 is substituted or unsubstituted alkylene, etc., R4 is hydrogen, substituted or unsubstituted alkanoyl, substituted or unsubstituted alkyl, etc., R5 is hydrogen, etc., or a salt thereof. These compounds being able to inhibit infiltration of leukocytes such as eosinophils and lymphocytes, and are, therefore, useful for the treatment of various kinds of inflammation.

Claims (24)

1. A 5-membered cyclic compound of the formula:

wherein X is an oxygen atom or a sulfur atom, R1 is a hydrogen atom, a substituted or unsubstituted alkyl, a substituted or unsubstituted aryl, or a substituted or unsubstituted heteromonocyclic or heterobicyclic group, R2 is a hydrogen atom, a substituted or unsubstituted alkyl, a substituted or unsubstituted aryl, a substituted or unsubstituted heteromonocyclic or heterobicyclic group, or -CON(R6)R7, R6 is a hydrogen atom, or a substituted or unsubstituted alkyl, R7 is a substituted or unsubstituted aryl, a substituted or unsubstituted heteromonocyclic group, or a substituted or unsubstituted alkyl, or -N(R6)R7 may be a cyclic imino group, Y1 is a direct bond, a substituted or unsubstituted alkylene, -CO(CH2)n-, -SO2(CH2)n-, -CONH(CH2)n-, -CSNH(CH2)n-, Or -COO(CH2)n-, n is an integer of from 0 to 5, the wavy line means (E)-configuration or (Z)-configuration, R3 is a hydrogen atom, a substituted or unsubstituted aryl, a substituted or unsubstituted heteromonocyclic group, a substituted or unsubstituted heterobicyclic group, or a substituted or unsubstituted cycloalkyl, Y2 is a substituted or unsubstituted alkylene, or an alkenylene, R4 is a hydrogen atom, a substituted or unsubstituted alkanoyl, a substituted or unsubstituted alkyl, -COOR8, -SO2R9, -COR10, -CON(R11)R12, -CSN(R13)R14, a cycloalkyl, a substituted or unsubstituted aryl, a substituted or unsubstituted heteromonocyclic group, -C(=NH)N(R15)R16, R5 is a hydrogen atom, or a substituted or unsubstituted alkyl, or -N(R4)R5 may be a cyclic imino group, R8 is a substituted or unsubstituted alkyl, a cycloalkyl, a substituted or unsubstituted aryl, or a substituted or unsubstituted heteromonocyclic group, R9 is a substituted or unsubstituted alkyl, a substituted or unsubstituted aryl, or a substituted or unsubstituted heteromonocyclic group, R10 is a cycloalkyl, a substituted or unsubstituted aryl, or a substituted or unsubstituted heteromonocyclic group, R11 is a hydrogen atom or an alkyl, R12 is a hydrogen atom, a substituted or unsubstituted alkyl, a cycloalkyl, a substituted or unsubstituted aryl, a substituted or unsubstituted arylcarbonyl, or a substituted or unsubstituted heteromonocyclic group, or a-N(R11)R12 may be a cyclic imino group, R13 is a hydrogen atom or an alkyl, R14 is a hydrogen atom, a substituted or unsubstituted alkyl, a cycloalkyl, a substituted or unsubstituted aryl, a substituted or unsubstituted arylcarbonyl, or a substituted or unsubstituted heteromonocyclic group, or -N(R13)R14 may be a cyclic imino group, R15 is a hydrogen atom or an alkyl, R16 is a hydrogen atom or a substituted or unsubstituted alkyl, or -N(R15)R16 may be a cyclic imino group, or a pharmaceutically acceptable salt thereof, or a prodrug thereof.
2. The 5-membered cyclic compound according to claim 1, provided that when Y1 is a direct bond, then -N(R4)R5 is neither an amino, nor a dialkylamino, nor an acetylamino, or a pharmaceutically acceptable salt thereof, or a prodrug thereof.
3. The 5-membered cyclic compound according to claim 1, which is a compound of the formula:
wherein X is an oxygen atom or a sulfur atom, R1 is a hydrogen atom, a substituted or unsubstituted alkyl, a substituted or unsubstituted aryl, or a substituted or unsubstituted heterobicyclic group, R2 is a hydrogen atom, a substituted or unsubstituted alkyl, a substituted or unsubstituted aryl, or a substituted or unsubstituted heterobicyclic group, Y1 is a direct bond, a substituted or unsubstituted alkylene, -CO(CH2)n-, or -SO2(CH2)n- (n is an integer of from 0 to 5), the wavy line means (E)-configuration or (Z)-configuration, R3 is a substituted or unsubstituted aryl, a substituted or unsubstituted 5- or 6-membered heteromonocyclic group, or a substituted or unsubstituted heterobicyclic group, Y2 is a substituted or unsubstituted alkylene, or an alkenylene, R4 is a hydrogen atom, an alkanoyl, an aroyl, a substituted or unsubstituted alkyl, an alkylcarbamoyl, an alkoxycarbonyl, an alkylaminothiocarbonyl, an alkylsulfonyl, or a substituted or unsubstituted arylsulfonyl, R5 is a hydrogen atom, or a substituted or unsubstituted alkyl, or a pharmaceutically acceptable salt thereof, or a prodrug thereof.
4. The 5-membered cyclic compound according to claim 1, which is a compound of the formula:
wherein X is an oxygen atom or a sulfur atom, R1 is a hydrogen atom; an alkyl; an alkyl being substituted by a hydroxy group or a halogen atom; an aryl; an aryl which is substituted by one or more groups selected from the group consisting of an alkoxy, a halogen-substituted alkoxy, a hydroxy, a halogen atom, a cyano, an amino, a mono- or di-(alkyl)amino, a 5- or 6-membered cyclic imino group having optionally an oxygen atom or a nitrogen atom as a heteroatom for ring formation, a nitro, an alkyl, an alkyl being substituted by a halogen atom or a hydroxy, a cycloalkyl, a cycloalkyl-substituted alkyl, a methylenedioxy, an ethylenedioxy, a carboxy, an alkoxycarbonyl, a carbamoyl, an alkylcarbamoyl, a di(alkyl)carbamoyl, an alkylthio, an alkylsulfinyl, an alkylsulfonyl, a sulfamoyl, an alkylsulfamoyl, a di(alkyl)sulfamoyl, an aryl, and an aryl being substituted by an alkyl, an alkoxy, a halogen atom or a hydroxy; a heterobicyclic group which is formed by condensing a benzene ring with a 5- or 6-membered heterocyclic group containing 1 to 3 heteroatoms selected from a nitrogen atom, an oxygen atom and a sulfur atom; or a heterobicyclic group which is formed by condensing a benzene ring with a 5- or 6-membered heterocyclic group being substituted by an alkyl, an alkoxy, a halogen atom or a hydroxy, and containing 1 to 3 heteroatoms selected from a nitrogen atom, an oxygen atom and a sulfur atom, R2 is a hydrogen atom; an alkyl; an alkyl being substituted by a hydroxy, a halogen atom or an amino; an aryl; an aryl being substituted one or more groups selected from the group consisting of an alkoxy, a halogen-substituted alkoxy, a hydroxy, a halogen atom, a cyano, an amino, a mono- or di-(alkyl)amino, a 5- or 6-membered cyclic imino group having optionally an oxygen atom or a nitrogen atom as a heteroatom for ring formation, a nitro, an alkyl, an alkyl being substituted by a halogen atom or a hydroxy, a cycloalkyl, a cycloalkyl-substituted alkyl, methylenedioxy, ethylenedioxy, a carboxy, an alkoxy-carbonyl, a carbamoyl, an alkylcarbamoyl, a di(alkyl)carbamoyl, an alkylthio, an alkylsulfinyl, an alkylsulfonyl, sulfamoyl, an alkylsulfamoyl, a di(alkyl) sulfamoyl, an aryl, and an aryl being substituted by an alkyl, an alkoxy, a halogen atom, or a hydroxy; a heterobicyclic group which is formed by condensing a benzene ring with a 5- or 6-membered heterocyclic group containing 1 to 3 heteroatoms selected from a nitrogen atom, an oxygen atom and a sulfur atom; or a heterobicyclic group which is formed by condensing a benzene ring with a 5- or 6-membered heterocyclic group being substituted by an alkyl, an alkoxy, a halogen atom or a hydroxy, and containing 1 to 3 heteroatoms selected from a nitrogen atom, an oxygen atom and a sulfur atom, Y1 is a direct bond; a straight chain or branched chain C1-C5 alkylene; a straight chain or branched chain C1-C5 alkylene being substituted by a hydroxy, a halogen atom or an amino;
-CO(CH2)n-; -SO2(CH2)n- (n is an integer of from 0 to 5), R3 is an aryl; an aryl being substituted by one or more groups selected from the group consisting of an alkoxy, a halogen-substituted alkoxy, a hydroxy, a halogen atom, a cyano, an amino, a mono- or di-(alkyl)amino, a nitro, an alkyl, an alkyl being substituted by a halogen atom or a hydroxy, a cycloalkyl, a cycloalkyl-substituted alkyl, methylenedioxy, ethylenedioxy, a carboxy, an alkoxycarbonyl, a carbamoyl, an alkylcarbamoyl, a di-(alkyl)carbamoyl, an alkylthio, an alkylsulfinyl, an alkylsulfonyl, a sulfamoyl, an alkylsulfamoyl, a di-(alkyl)sulfamoyl, an aryl, and an aryl being substituted by an alkyl, an alkoxy, a halogen atom or a hydroxy; a 5- or 6-membered heteromono-cyclic group containing 1 to 3 heteroatoms selected from a nitrogen atom, an oxygen atom and a sulfur atom; a 5- or 6-membered heteromono-cyclic group being substituted by an alkyl, an alkoxy, a halogen atom or a hydroxy, and containing 1 to 3 heteroatoms selected from a nitrogen atom, an oxygen atom and a sulfur atom; a heterobicyclic group which is formed by condensing a benzene ring with a 5- or 6-membered hetero-cyclic group containing 1 to 3 heteroatoms selected from a nitrogen atom, an oxygen atom and a sulfur atom; or a heterobicyclic group which is formed by condensing a benzene ring with a 5- or 6-membered hetero-cyclic group being substituted by an alkyl, an alkoxy, a halogen atom or a hydroxy and containing 1 to 3 heteroatoms selected from a nitrogen atom, an oxygen atom and a sulfur atom, Y2 is a straight chain or branched chain C2-C5 alkylene; a straight chain or branched chain C2-C5 alkylene being substituted by a hydroxy, an alkoxy, a halogen atom, an amino or an alkanoylamino; or a straight chain or branched chain C3-C5 alkenylene, R4 is a hydrogen atom; an alkanoyl; an aroyl; an alkyl; an alkyl being substituted by a hydroxy, an alkoxy, a halogen atom or an amino:
an alkylcarbamoyl; an alkoxycarbonyl; an alkylaminothiocarbonyl; an alkylsulfonyl; an arylsufonyl; or an alkyl-substituted arylsulfonyl, R5 is a hydrogen; an alkyl; or an alkyl being substituted by a hydroxy, a halogen atom or an amino, or a pharmaceutically acceptable salt thereof, or a prodrug thereof.
5. The 5-membered cyclic compound according to any one of claims 1 to 4, wherein X is a sulfur atom, or a pharmaceutically acceptable salt thereof, or a prodrug thereof.
6. The 5-membered cyclic compound according to any one of claims 1 to 5, wherein R1 is a hydrogen atom, or a pharmaceutically acceptable salt thereof, or a prodrug thereof.
7. The 5-membered cyclic compound according to any one of claims 1 to 6, wherein R2 is a substituted or unsubstituted alkyl, a substituted or unsubstituted aryl, a substituted or unsubstituted heteromonocyclic or heterobicyclic group, -CON(R6)R7, or a substituted or unsubstituted heterocyclic carbonyl, or a pharmaceutically acceptable salt thereof, or a prodrug thereof.
8. The 5-membered cyclic compound according to any one of claims 1 to 6, wherein R2 is a substituted or unsubstituted aryl, or a pharmaceutically acceptable salt thereof, or a prodrug thereof.
9. The 5-membered cyclic compound according to any one of claims 1 to 8, wherein Y1 is a substituted or unsubstituted alkylene, -CO(CH2)n-, -SO2(CH2)n-, -CONH(CH2)n-, -CSNH(CH2)n-, or -COO(CH2)n-, or a pharmaceutically acceptable salt thereof, or a prodrug thereof.
10. The 5-membered cyclic compound according to any one of claims 1 to 8, wherein Y1 is a direct bond, -CO-, -SO2-, -CONH-, or -COO-, or a pharmaceutically acceptable salt thereof, or a prodrug thereof.
11. The 5-membered cyclic compound according to any one of claims 1 to 8, wherein Y1 is a direct bond or a -CO-, or a pharmaceutically acceptable salt thereof, or a prodrug thereof.
12. The 5-membered cyclic compound according to any one of claims 1 to 11, wherein R3 is a substituted or unsubstituted aryl, or a substituted or unsubstituted heteromonocyclic group, or a pharmaceutically acceptable salt thereof, or a prodrug thereof.
13. The 5-membered cyclic compound according to any one of claims 1 to 12, wherein the wavy line means (Z)-configuration, or a pharmaceutically acceptable salt thereof, or a prodrug thereof.
14. The 5-membered cyclic compound according to any one of claims 1 to 13, wherein Y2 is ethylene or trimethylene, or a pharmaceutically acceptable salt thereof, or a prodrug thereof.
15. The 5-membered cyclic compound according to any one of claims 1 to 14, wherein R4 is a substituted or unsubstituted alkanoyl, a substituted or unsubstituted alkyl, a substituted or unsubstituted alkylcarbamoyl, a substituted or unsubstituted alkylaminothiocarbonyl, or a substituted or unsubstituted alkoxycarbonyl, or a pharmaceutically acceptable salt thereof, or a prodrug thereof.
16. The 5-membered cyclic compound according to any one of claims 1 to 14, wherein R4 is a substituted or unsubstituted alkanoyl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted alkylcarbamoyl, or a pharmaceutically acceptable salt thereof, or a prodrug thereof.
17. The 5-membered cyclic compound according to any one of claims 1 to 15, wherein R5 is a hydrogen atom, or a pharmaceutically acceptable salt thereof, or a prodrug thereof.
18. The 5-membered cyclic compound according to claim 1, which is a compound of the formula:

wherein Ring A is a benzene ring or a pyridine ring, m is 2 or 3, Y3 is a direct bond or a carbonyl, the number of R17 is 1 or 2, and R17s are independently selected from a halogen atom, a C1-C4 alkoxy, a trifluoromethoxy, a morpholino and a methylenedioxy, the number of R18 is 1 or 2, and R18s are independently selected from a halogen atom, a C1-C4 alkoxy, a trifluoromethoxy and a hydroxy, R19 is a Cl-C4 alkyl; a C1-C4 alkyl being substituted by a hydroxy, a C1-C4 alkoxy, a mono- or di-(C1-C4 alkyl)amino, a morpholino or a carboxy; a C1-C4 alkylamino; or a C1-C4 alkylamino being substituted by a hydroxy, a C1-C4 alkoxy, a mono- or di-(C1-C4 alkyl)amino, a morpholino or a carboxy, or a pharmaceutically acceptable salt thereof, or a prodrug thereof.
19. The 5-membered cyclic compound according to claim 18, provided that when Y3 is a direct bond, then R19 is not a methyl, or a pharmaceutically acceptable salt thereof, or a prodrug thereof.
20. The 5-membered cyclic compound according to claim 8, wherein Ring A is a benzene ring, (i) Y3 is a direct bond and R19 is a C1-C4 alkylamino, or (ii) Y3 is a carbonyl and R19 is a Cl-C4 alkyl, or a pharmaceutically acceptable salt thereof, or a prodrug thereof.
21. A medicament, which comprises the 5-membered cyclic compound as set forth in any one of claims 1 to 20, or a pharmaceutically acceptable salt thereof, or a prodrug thereof.
22. A leukocyte infiltration inhibitor, which comprises the 5-membered cyclic compound as set forth in any one of claims 1 to 20, or a pharmaceutically acceptable salt thereof, or a prodrug thereof,
23. An agent for treatment of inflammation, which comprises the 5-membered cyclic compound as set forth in any one of claims 1 to 20, or a pharmaceutically acceptable salt thereof, or a prodrug thereof.
24. An agent for treatment of autoimmune inflammation or allergic inflammation, which comprises the 5-membered cyclic compound as set forth in any one of claims 1 to 20, or a pharmaceutically acceptable salt thereof, or a prodrug thereof.
CA002413000A 2000-06-30 2001-06-28 Five-membered ring compounds Expired - Fee Related CA2413000C (en)

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