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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
Authority
WO
WIPO (PCT)
Prior art keywords
lower alkyl
phenyl
halo
hydrogen
pyranoindole
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/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
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.)
Wyeth LLC
Original Assignee
American Home Products Corp
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 Products Corp filed Critical American Home Products Corp
Priority to BR909007790A priority Critical patent/BR9007790A/pt
Priority to KR1019920700971A priority patent/KR920702345A/ko
Publication of WO1991006537A2 publication Critical patent/WO1991006537A2/fr
Publication of WO1991006537A3 publication Critical patent/WO1991006537A3/fr
Priority to FI921865A priority patent/FI921865A7/fi
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Immunology (AREA)
  • Pulmonology (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 Ceased WO1991006537A2 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
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
KR1019920700971A KR920702345A (ko) 1989-10-27 1990-10-27 Pla_2및 리폭시게나제의 억제제로서의 치환된 인돌-,인덴-,피라노인돌-및 테트라하이드로카바졸-알칸산 유도체
FI921865A FI921865A7 (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
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 (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 Ceased 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) FI921865A7 (fr)
HU (1) HUT63407A (fr)
IE (1) IE903872A1 (fr)
PT (1) PT95692A (fr)
WO (1) WO1991006537A2 (fr)

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US11459338B2 (en) 2017-11-24 2022-10-04 Jubilant Episcribe Llc Heterocyclic compounds as PRMT5 inhibitors
US11529341B2 (en) 2018-03-13 2022-12-20 Jubilant Prodel LLC Bicyclic compounds as inhibitors of PD1/PD-L1 interaction/activation
US11555015B2 (en) 2018-09-06 2023-01-17 Arena Pharmaceuticals, Inc. Compounds useful in the treatment of autoimmune and inflammatory disorders
US11629135B2 (en) 2017-11-06 2023-04-18 Jubilant Prodell Llc Pyrimidine derivatives as inhibitors of PD1/PD-L1 activation
US11833156B2 (en) 2017-09-22 2023-12-05 Jubilant Epipad LLC Heterocyclic compounds as pad inhibitors

Families Citing this family (57)

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US5229516A (en) * 1989-10-27 1993-07-20 American Home Products Corporation Substituted indole-, indene-, pyranoindole- and tetrahydrocarbazole-alkanoic acid derivatives as inhibitors of PLA2 and lipoxygenase
US5187180A (en) * 1990-07-26 1993-02-16 Merck Frosst Canada, Inc. (quinolin-2-ylmethoxy)heterotetrahydrocarbazoles as inhibitors of the biosynthesis of leukotrienes
US5221678A (en) * 1990-07-26 1993-06-22 Merck Frosst Canada, Inc. (quinolin-2-ylmethoxy)tetrahydrocarbazoles as inhibitors of the biosynthesis of leukotrienes
US5308850A (en) * 1991-09-30 1994-05-03 Merck Frosst Canada, Inc. (Bicyclic-hetero-arylmethoxy)indoles as inhibitors of leukotriene biosynthesis
US5389650A (en) * 1991-09-30 1995-02-14 Merck Frosst Canada, Inc. (Azaarylmethoxy)indoles as inhibitors of leukotriene biosynthesis
US5190968A (en) * 1991-09-30 1993-03-02 Merck Frosst Canada, Inc. (Polycyclic-arylmethoxy) indoles as inhibitors of leukotriene biosynthesis
US5290798A (en) * 1991-09-30 1994-03-01 Merck Frosst Canada, Inc. (hetero-arylmethoxy)indoles as inhibitors of leukotriene biosynthesis
CA2079374C (fr) * 1991-09-30 2003-08-05 Merck Frosst Canada Incorporated Indol (azaarylmethoxy bicyclique) comme inhibiteur de leucotriene biosynthetique
GB9122590D0 (en) * 1991-10-24 1991-12-04 Lilly Industries Ltd Pharmaceutical compounds
CA2129429A1 (fr) * 1992-02-13 1993-08-14 Richard Frenette (azaaromaticalkoxy) indoles utilises comme inhibiteurs de la biosynthese de la leucotriene
DE4219765A1 (de) * 1992-06-17 1993-12-23 Bayer Ag Substituierte (Benzothiazolyl- und Chinoxalyl-methoxy)phenylessigsäurederivate
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BRPI0916812B8 (pt) * 2008-07-23 2022-10-18 Arena Pharm Inc Derivados do ácido 1,2,3,4-tetra-hidrociclopenta[b]indol-3-il)acético substituído úteis no tratamento de distúrbios autoimunes e inflamatórios, seu uso, composição farmacêutica que os compreende e processo de preparação
PT2342205T (pt) 2008-08-27 2016-07-28 Arena Pharm Inc Derivados de ácido tricíclico substituído como agonistas de recetor s1p1 úteis no tratamento de distúrbios autoimunes e inflamatórios
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CN102884064B (zh) 2010-03-03 2016-01-13 艾尼纳制药公司 制备s1p1受体调节剂及其晶体形式的方法
UA126268C2 (uk) 2015-01-06 2022-09-14 Арена Фармасьютікалз, Інк. СПОСОБИ ЛІКУВАННЯ СТАНІВ, ПОВ'ЯЗАНИХ З РЕЦЕПТОРОМ S1P<sub>1 </sub>
MA42807A (fr) 2015-06-22 2018-07-25 Arena Pharm Inc Sel l-arginine cristallin d'acide (r)-2-(7-(4-cyclopentyl-3-(trifluorométhyl)benzyloxy)-1,2,3,4-tétrahydrocyclo-penta[b]indol-3-yl)acétique (composé 1) pour une utilisation dans des troubles associés au récepteur de s1p1
WO2017073060A1 (fr) * 2015-10-29 2017-05-04 国立大学法人東北大学 Inhibiteur de production de collagène
MA47504A (fr) 2017-02-16 2019-12-25 Arena Pharm Inc Composés et méthodes de traitement de l'angiocholite biliaire primitive
AU2018222747A1 (en) 2017-02-16 2019-09-05 Arena Pharmaceuticals, Inc. Compounds and methods for treatment of inflammatory bowel disease with extra-intestinal manifestations
US11426412B2 (en) 2017-10-18 2022-08-30 Jubilant Epipad LLC Imidazo-pyridine compounds as PAD inhibitors
KR102859841B1 (ko) 2018-06-06 2025-09-12 아레나 파마슈티칼스, 인크. S1p1 수용체와 관련된 병태의 치료 방법
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DE1816993A1 (de) * 1967-12-27 1969-10-16 Lodzkie Zaklady Farma Verfahren zur Herstellung von 1-Aoyl- oder 1-Heteroaroyl- oder 1-Benzheteroaroyl-2-methyl-5-alkoxy-(oder 5-aralkoxy)-indolyl-3-essigsaeuren
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US12357639B2 (en) 2017-09-22 2025-07-15 Jubilant Epipad LLC Heterocyclic compounds as pad inhibitors
US11629135B2 (en) 2017-11-06 2023-04-18 Jubilant Prodell Llc Pyrimidine derivatives as inhibitors of PD1/PD-L1 activation
US11459338B2 (en) 2017-11-24 2022-10-04 Jubilant Episcribe Llc Heterocyclic compounds as PRMT5 inhibitors
US11529341B2 (en) 2018-03-13 2022-12-20 Jubilant Prodel LLC Bicyclic compounds as inhibitors of PD1/PD-L1 interaction/activation
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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CA2070422A1 (fr) 1991-04-28
AU643996B2 (en) 1993-12-02
FI921865A0 (fi) 1992-04-24
JPH05502222A (ja) 1993-04-22
HUT63407A (en) 1993-08-30
WO1991006537A2 (fr) 1991-05-16
KR920702345A (ko) 1992-09-03
IE903872A1 (en) 1991-05-22
PT95692A (pt) 1991-09-13
FI921865A7 (fi) 1992-04-24
AU7740491A (en) 1991-05-31
EP0502106A1 (fr) 1992-09-09
BR9007790A (pt) 1992-09-15

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