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WO1991006537A3 - Derives d'acide alcanoique indole, indene, pyranoindole et tetrahydrocarbazole substitues utilises comme inhibiteurs de la phospholipase a2 (pla2) et de la lipoxygenase - Google Patents

Derives d'acide alcanoique indole, indene, pyranoindole et tetrahydrocarbazole substitues utilises comme inhibiteurs de la phospholipase a2 (pla2) et de la 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
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English (en)
Other versions
WO1991006537A2 (fr
Inventor
John Henry Musser
Anthony Frank Kreft Iii
Amedeo Arturo Failli
Christopher Alexander Demerson
Uresh Shantilal Shah
James Albert Nelson
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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 KR1019920700971A priority Critical patent/KR920702345A/ko
Priority to BR909007790A priority patent/BR9007790A/pt
Publication of WO1991006537A2 publication Critical patent/WO1991006537A2/fr
Publication of WO1991006537A3 publication Critical patent/WO1991006537A3/fr
Priority to FI921865A priority patent/FI921865A0/fi

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

Abstract

L'invention se rapporte à des composés représentés par la formule: A(CH2)nO-B, où: A représente un alkyle C4-C8, un phénoxyéthyle, un phénoxyphényle ou un groupe ayant la formule (a) ou (b), où X représente -N- ou (c), Z représente (d), (e), (f), (g), -S- ou -O-, R1 représente l'hydrogène, un alkyle inférieur, un phényle ou un phényle substitué par un trifluorométhyle, R2 représente l'hydrogène ou un alkyle inférieur ou R1 et R2 forment ensemble une chaîne fermée de benzène, R3 représente l'hydrogène ou un alkyle inférieur; n est égal à 1 ou à 2; B représente un groupe ayant la formule (h), (i), (j) ou (k), où R4 représente -CO¿2R?2, (l), (m), (n), (o) ou (p), m est égal à un nombre compris entre 0 et 3, R5 représente (q), un phényle ou un phényle substitué par un halo, un alkylthio inférieur, un alkylsulfinyle inférieur ou un alkyle sulfonyle inférieur, R6 représente A(CH¿2?)no- ou un halo, à la condition que, lorsque R?6¿ représente un halo, R5 représente (r), R7 représente un alkyle inférieur, Y représente -CH¿2?- ou -O-, R?8¿ représente un alkyle inférieur ou -(CH¿2?)mCO2R?3; R9¿ représente (s) ou -CH¿2?R?10, R10¿ représente un alkyle inférieur, un phényle, un phényle substitué par un carboxy, un halo, un alkylthio inférieur ou un alkylsulfinyle inférieur, un pyridyle, un furanyle ou un quinolinyle, R11 représente un alkyle ou un phényle inférieur; ainsi qu'aux sels pharmacologiquement acceptables de tels composés, et à leur utilisation dans le traitement d'états inflammatoires, tels que l'arthrite rhumatoïde, la colite ulcérative, le psoriasis et d'autres réactions d'hypersensibilité immediate, dans le traitement d'états obstructifs des voies bronchonasales se développant par l'intermédiaire de la leukotriène, telle que la rhinite allergique, l'asthme bronchique allergique et similaires, et comme agents cytoprotecteurs gastriques.
PCT/US1990/006251 1989-10-27 1990-10-27 Derives d'acide alcanoique indole, indene, pyranoindole et tetrahydrocarbazole substitues utilises comme inhibiteurs de la phospholipase a2 (pla2) et de la lipoxygenase WO1991006537A2 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
KR1019920700971A KR920702345A (ko) 1989-10-27 1990-10-27 Pla_2및 리폭시게나제의 억제제로서의 치환된 인돌-,인덴-,피라노인돌-및 테트라하이드로카바졸-알칸산 유도체
BR909007790A BR9007790A (pt) 1989-10-27 1990-10-27 Derivados de acidos indol-,indeno-,piranoindol-e tetrahidrocarbazol-alcanoicos substituidos como inibidores de pla2 e lipoxigenase
FI921865A FI921865A0 (fi) 1989-10-27 1992-04-24 Substituerade indol-, inden-, pyranoindol- och tetrahydrokarbazol-alkansyraderivat som inhibitorer av pla2 och lipoxigenas.

Applications Claiming Priority (4)

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

Publications (2)

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

Family

ID=27027687

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1990/006251 WO1991006537A2 (fr) 1989-10-27 1990-10-27 Derives d'acide alcanoique indole, indene, pyranoindole et tetrahydrocarbazole substitues utilises comme inhibiteurs de la phospholipase a2 (pla2) et de la lipoxygenase

Country Status (11)

Country Link
EP (1) EP0502106A1 (fr)
JP (1) JPH05502222A (fr)
KR (1) KR920702345A (fr)
AU (1) AU643996B2 (fr)
BR (1) BR9007790A (fr)
CA (1) CA2070422A1 (fr)
FI (1) FI921865A0 (fr)
HU (1) HUT63407A (fr)
IE (1) IE903872A1 (fr)
PT (1) PT95692A (fr)
WO (1) WO1991006537A2 (fr)

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Publication number Priority date Publication date Assignee Title
US11555015B2 (en) 2018-09-06 2023-01-17 Arena Pharmaceuticals, Inc. Compounds useful in the treatment of autoimmune and inflammatory disorders

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KR920702345A (ko) 1992-09-03
PT95692A (pt) 1991-09-13
AU643996B2 (en) 1993-12-02
CA2070422A1 (fr) 1991-04-28
FI921865A7 (fi) 1992-04-24
EP0502106A1 (fr) 1992-09-09
BR9007790A (pt) 1992-09-15
IE903872A1 (en) 1991-05-22
AU7740491A (en) 1991-05-31
JPH05502222A (ja) 1993-04-22
HUT63407A (en) 1993-08-30
WO1991006537A2 (fr) 1991-05-16
FI921865A0 (fi) 1992-04-24

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