WO1991006537A3 - Substituted indole-, indene-, pyranoindole- and tetrahydrocarbazole- alkanoic acid derivatives as inhibitors of pla2 and lipoxygenase - Google Patents

Substituted indole-, indene-, pyranoindole- and tetrahydrocarbazole- alkanoic acid derivatives as inhibitors of pla2 and lipoxygenase Download PDF

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Publication number
WO1991006537A3
WO1991006537A3 PCT/US1990/006251 US9006251W WO9106537A3 WO 1991006537 A3 WO1991006537 A3 WO 1991006537A3 US 9006251 W US9006251 W US 9006251W WO 9106537 A3 WO9106537 A3 WO 9106537A3
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WO
WIPO (PCT)
Prior art keywords
lower alkyl
phenyl
halo
hydrogen
pyranoindole
Prior art date
Application number
PCT/US1990/006251
Other languages
French (fr)
Other versions
WO1991006537A2 (en
Inventor
John Henry Musser
Anthony Frank Kreft Iii
Amedeo Arturo Failli
Christopher Alexander Demerson
Uresh Shantilal Shah
James Albert Nelson
Original Assignee
American Home Prod
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
Application filed by American Home Prod filed Critical American Home Prod
Priority to BR909007790A priority Critical patent/BR9007790A/en
Priority to KR1019920700971A priority patent/KR920702345A/en
Publication of WO1991006537A2 publication Critical patent/WO1991006537A2/en
Publication of WO1991006537A3 publication Critical patent/WO1991006537A3/en
Priority to FI921865A priority patent/FI921865A/en

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Classifications

    • 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
    • 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
    • A61P37/08—Antiallergic agents
    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D209/22—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an aralkyl radical attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D215/14—Radicals substituted by oxygen 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
    • C07D401/14—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 three or more hetero rings
    • 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
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems

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

Abstract

There are disclosed compounds of the formula: A(CH2)nO-B, wherein A is C4-C8 alkyl, phenoxyethyl, phenoxyphenyl or a group having formula (a) or (b), wherein X is -N- or (c); Z is (d), (e), (f), (g), -S- or -O-; R1 is hydrogen, lower alkyl, phenyl or phenyl substituted with trifluoromethyl; R2 is hydrogen or lower alkyl; or R?1 and R2¿ taken together form a benzen ring; R3 is hydrogen or lower alkyl; n is 1-2; B is (h), (i), (j) or (k); wherein R4 is -CO¿2R?2, (l), (m), (n), (o) or (p); m is 0-3; R5 is (q); or phenyl or phenyl substituted by halo, lower alkylthio, lower alkylsulfinyl or lower alkylsulfonyl; R6 is A(CH¿2?)nO- or halo; with the proviso that when R?6¿ is halo, R5 is (r); R7 is lower alkyl; Y is -CH¿2?- or -O-; R?8¿ is lower alkyl or -(CH¿2?)mCO2R?3; R9¿ is (s) or -CH¿2?R?10; R10¿ is lower alkyl, phenyl, phenyl substituted with carboxy, halo, loweralkylthio or loweralkylsulfinyl, pyridyl, furanyl or quinolinyl; R11 is lower alkyl or phenyl; and the pharmacologically acceptable salts thereof, and their use in the treatment of inflammatory conditions, such as rheumatoid arthritis, ulcerative colitis, psoriasis and other immediate hypersensitivity reactions; in the treatment of leukotriene-mediated naso-bronchial obstructive air-passageway conditions, such as allergic rhinitis, allergic bronchial asthma and the like; and as gastric cytoprotective agents.
PCT/US1990/006251 1989-10-27 1990-10-27 Substituted indole-, indene-, pyranoindole- and tetrahydrocarbazole- alkanoic acid derivatives as inhibitors of pla2 and lipoxygenase WO1991006537A2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
BR909007790A BR9007790A (en) 1989-10-27 1990-10-27 DERIVATIVES OF INDOL-, INDENO-, PYRANINDOL-AND TETRAHYDROCARBAZOL-ALKANOIC ACIDS REPLACED AS PLA2 AND LIPOXYGENASE INHIBITORS
KR1019920700971A KR920702345A (en) 1989-10-27 1990-10-27 Substituted indole-, indene-, pyranoindole- and tetrahydrocarbazole-alkanoic acid derivatives as inhibitors of PLA_2 and lipoxygenase
FI921865A FI921865A (en) 1989-10-27 1992-04-24 SUBSTITUERADE INDOL-, INDEN-, PYRANOINDOL- OCH TETRAHYDROCARBAZOLE-ALKANSYRADERIVAT SOM INHIBITORER AV PLA2 OCH LIPOXIGENAS.

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US596,134 1984-04-02
US42826089A 1989-10-27 1989-10-27
US428,260 1989-10-27
US59613490A 1990-10-11 1990-10-11

Publications (2)

Publication Number Publication Date
WO1991006537A2 WO1991006537A2 (en) 1991-05-16
WO1991006537A3 true WO1991006537A3 (en) 1991-10-17

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PCT/US1990/006251 WO1991006537A2 (en) 1989-10-27 1990-10-27 Substituted indole-, indene-, pyranoindole- and tetrahydrocarbazole- alkanoic acid derivatives as inhibitors of pla2 and lipoxygenase

Country Status (11)

Country Link
EP (1) EP0502106A1 (en)
JP (1) JPH05502222A (en)
KR (1) KR920702345A (en)
AU (1) AU643996B2 (en)
BR (1) BR9007790A (en)
CA (1) CA2070422A1 (en)
FI (1) FI921865A (en)
HU (1) HUT63407A (en)
IE (1) IE903872A1 (en)
PT (1) PT95692A (en)
WO (1) WO1991006537A2 (en)

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Publication number Priority date Publication date Assignee Title
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Also Published As

Publication number Publication date
AU7740491A (en) 1991-05-31
BR9007790A (en) 1992-09-15
IE903872A1 (en) 1991-05-22
KR920702345A (en) 1992-09-03
CA2070422A1 (en) 1991-04-28
JPH05502222A (en) 1993-04-22
FI921865A0 (en) 1992-04-24
PT95692A (en) 1991-09-13
WO1991006537A2 (en) 1991-05-16
EP0502106A1 (en) 1992-09-09
AU643996B2 (en) 1993-12-02
HUT63407A (en) 1993-08-30
FI921865A (en) 1992-04-24

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