GB1285398A - Hydroxy-substituted tricyclic carboxylic acids and derivatives and pharmaceutical compositions containing them - Google Patents

Hydroxy-substituted tricyclic carboxylic acids and derivatives and pharmaceutical compositions containing them

Info

Publication number
GB1285398A
GB1285398A GB2953670A GB2953670A GB1285398A GB 1285398 A GB1285398 A GB 1285398A GB 2953670 A GB2953670 A GB 2953670A GB 2953670 A GB2953670 A GB 2953670A GB 1285398 A GB1285398 A GB 1285398A
Authority
GB
United Kingdom
Prior art keywords
fluoro
amino
hydroxy
bromo
chloro
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.)
Expired
Application number
GB2953670A
Inventor
Tsung-Ying Shen
Gordon Lyn Walford
Bruce Edward Witzel
William Vance Ruyle
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
Application filed by Merck and Co Inc filed Critical Merck and Co Inc
Publication of GB1285398A publication Critical patent/GB1285398A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
    • C07C205/46—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group the carbon skeleton containing carbon atoms of quinone rings
    • 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
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/88—Carbazoles; Hydrogenated carbazoles 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 carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/76—Dibenzothiophenes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1285398 Hydroxy-tricyclic carboxylic acids MERCK & CO Inc 18 June 1970 [25 June 1969 20 April 1970] 29536/70 Heading C2C Novel compounds of the Formula (I) wherein X denotes hydrogen, alkyl, hydroxy, alkoxy, acyloxy, halogen, haloalkyl, nitro, amino, alkylamino, dialkylamino, acylamino, mercapto, alkylmercapto, alkylsulphinyl, alkylsulphonyl, sulphamoyl, aminosulphinyl, aminoalkyl, alkylaminoalkyl, hydroxyalkyl, alkoxyalkyl, mercaptoalkyl, alkylthioalkyl, cyano, carboxy, alkoxycarbonyl, carbamoyl, aryl, aralkyl, aryloxy, aralkoxy and acyl; Y is oxy, thio, sulphinyl, sulphonyl, imino, and alkylimino; R is hydroxy, amino, alkoxy, alkylamino, dialkylaminoalkoxy, hydroxyalkoxy, polyhydroxyalkoxy, alkoxyalkoxy, arylalkoxy, phenoxy, substituted phenoxy, carboxy and alkoxy carbonyl, alkanoylaminoalkoxy, hydrazino, N - morpholino, and hydroxyalkylamino; N - (4 - alkyl)piperidino or N - (4- hydroxyalkyl piperidino) or an N-attached residue derived from an amino acid and R 2 is hydrogen, acyl, alkyl, or alkoxycarbonyl; provided that the 0R 2 group is always ortho to the COR group; and that when Y is imino or oxy at least one X is other than H, alkyl and hydroxy, may be obtained by reacting a compound of the Formula (II) with C0 2 at elevated temperatures and pressures. The corresponding esters, amides, anhydrides and salts of the resulting acid may be obtained by conventional procedures. The preparation of the following intermediates is also described: 7-fluoro-3-nitro-dibenzofuran, 7 - fluoro - 2 - nitrodibenzofuran, 8 - fluoro - 2- nitrodibenzofuran; 7 - fluoro - 3 - dibenzofuranamine, and other fluoro-, carboxy-, bromo-, and chloro-2- and 3-dibenzofuranamines; 7- fluoro - 3 - dibenzo - furanol and other carboxy-, methoxy-, nitro- or bromo- 3-dibenzofuranols; 4<SP>1 </SP>- fluoro-, 4<SP>1 </SP>- chloro-, 4<SP>1 </SP>- methoxy-, 41 - methyl- or 4<SP>1</SP> - trifluoromethyl - 2 - amino- 4 - nitrodiphenyl sulphide; 4<SP>1</SP> - fluoro-, 41- bromo-, 41 - chloro-, 41 - methyl, 41 - methoxy or 4<SP>1</SP>- trifluoromethyl 2 - amino - 5 - nitrodiphenylsulphide; 8 - fluoro - 2 - nitro - dibenzothiophene and similar 8-bromo, chloro, iodo-, methyl, methoxy or trifluoromethyl compounds; 7 - fluoro - 3 - nitrodibenzothiophene and corresponding 7-chloro, bromo and iodo compounds; and 5,5-dioxides corresponding to these dibenzothiophenes; 2-ammo-8-fluorodibenzothiophene and other 8-substituted-2- and 3-aminodibenzothiophenes and their 5,5-dioxides; 8- fluoro- and other 8-substituted 2- and 3- hydroxydibenzothiophenes and their 5,5-dioxides; 2 - (51 - fluoro - 21 - nitrophenyl)- benzoquinone and other 4- or 5- substituted, and 4,5 - disubstituted anologues; 2 - (21- amino-5<SP>1</SP>-fluorophenyl)hydroquinone. Pharmaceutical compositions comprising a compoundof Formula (I) together with a suitable carrier have anti-inflammatory activity and certain compositions also have anti-pyretic, analgesic, diuretic, anti-fibrinolytic and hypoglycemic activity. The composition may be administered orally, rectally, parenterally or topically.
GB2953670A 1969-06-25 1970-06-18 Hydroxy-substituted tricyclic carboxylic acids and derivatives and pharmaceutical compositions containing them Expired GB1285398A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US83660369A 1969-06-25 1969-06-25
US3036470A 1970-04-20 1970-04-20

Publications (1)

Publication Number Publication Date
GB1285398A true GB1285398A (en) 1972-08-16

Family

ID=26705950

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2953670A Expired GB1285398A (en) 1969-06-25 1970-06-18 Hydroxy-substituted tricyclic carboxylic acids and derivatives and pharmaceutical compositions containing them

Country Status (5)

Country Link
CA (1) CA952913A (en)
CH (1) CH549008A (en)
FR (1) FR2053028B1 (en)
GB (1) GB1285398A (en)
NL (1) NL7008628A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004089940A1 (en) * 2003-04-11 2004-10-21 Glenmark Pharmaceuticals S.A. Novel heterocyclic compounds useful for the treatment of inflammatory and allergic disorders: process for their preparation and pharmaceutical compositions containing them
US7238725B2 (en) 2002-10-23 2007-07-03 Glenmark Pharmaceuticals Ltd. Tricyclic compounds useful for the treatment of inflammatory and allergic disorders: process for their preparation and pharmaceutical compositions containing them
US7563900B2 (en) 2004-10-13 2009-07-21 Glenmark Pharmaceuticals S.A. Process for the preparation N-(3,5-dichloropyrid-4-yl)-4-difluoromethoxy-8-methane sulfonamido-dibenzo[b,d]furan-1-carboxamide
US7943634B2 (en) 2004-12-17 2011-05-17 Glenmark Pharmaceuticals S.A. Substituted benzo[4,5]furo[3,2-c]pyridine derivatives as PDE 4 inhibitors
US8129401B2 (en) 2004-12-17 2012-03-06 Glenmark Pharmaceuticals S.A. Heterocyclic compounds useful for the treatment of inflammatory and allergic disorders: process for their preparation and pharmaceutical compositions containing them

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH574433A5 (en) * 1971-03-26 1976-04-15 Hoffmann La Roche
DE2223391C3 (en) * 1972-05-13 1982-02-11 Merck Patent Gmbh, 6100 Darmstadt Dibenzofuran derivatives, processes for their production and pharmaceutical preparations containing these compounds
GB1458186A (en) * 1972-09-06 1976-12-08 Wellcome Found Oxides of sulphur-containing tricyclic compounds methods for their preparation and compositions containing them
BG25793A3 (en) * 1973-07-18 1978-12-12 Schering Ag A method of obtaining carbasole derivatives
MY122278A (en) 1999-07-19 2006-04-29 Upjohn Co 1,2,3,4,5,6-hexahydroazepino[4,5-b]indoles containing arylsulfones at the 9-position
US7030109B2 (en) 1999-07-19 2006-04-18 Pharmacia & Upjohn Company 1,2,3,4,5,6-Hexahydroazepino[4,5-b]indoles containing arylsulfones at the 9-position

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7238725B2 (en) 2002-10-23 2007-07-03 Glenmark Pharmaceuticals Ltd. Tricyclic compounds useful for the treatment of inflammatory and allergic disorders: process for their preparation and pharmaceutical compositions containing them
WO2004089940A1 (en) * 2003-04-11 2004-10-21 Glenmark Pharmaceuticals S.A. Novel heterocyclic compounds useful for the treatment of inflammatory and allergic disorders: process for their preparation and pharmaceutical compositions containing them
JP2006522789A (en) * 2003-04-11 2006-10-05 グレンマーク・ファーマシューティカルズ・エス・エー Novel heterocyclic compounds useful for the treatment of inflammatory and allergic disorders; methods for their preparation and pharmaceutical compositions
US7223789B2 (en) 2003-04-11 2007-05-29 Glenmark Pharmaceuticals S.A. Heterocyclic compounds useful for the treatment of inflammatory and allergic disorders: process for their preparation and pharmaceutical compositions containing them
US7384962B2 (en) 2003-04-11 2008-06-10 Glenmark Pharmaceuticals S.A. Heterocyclic compounds useful for the treatment of inflammatory and allergic disorders: process for their preparation and pharmaceutical compositions containing them
US7393846B2 (en) 2003-04-11 2008-07-01 Glenmark Pharmaceuticals, S.A. Heterocyclic compounds useful for the treatment of inflammatory and allergic disorders
EA010634B1 (en) * 2003-04-11 2008-10-30 Гленмарк Фармасьютикалс С.А. Novel heterocyclic compounds useful for thr treatment of inflammatory and allergic disorders:process for their preparation and pharmaceutical compositions containing them
AP2008A (en) * 2003-04-11 2009-06-29 Glenmark Pharmaceuticals Sa Novel heterocyclic compounds useful for the treatment of inflammatory and allergic disorders; process for their preparation and pharmaceutical compositions containing them
CN1829711B (en) * 2003-04-11 2010-06-16 格兰马克药品股份有限公司 Novel heterocyclic compounds useful for the treatment of inflammatory and allergic disorders, process for their preparation and pharmaceutical compositions containing them
US7563900B2 (en) 2004-10-13 2009-07-21 Glenmark Pharmaceuticals S.A. Process for the preparation N-(3,5-dichloropyrid-4-yl)-4-difluoromethoxy-8-methane sulfonamido-dibenzo[b,d]furan-1-carboxamide
US7943634B2 (en) 2004-12-17 2011-05-17 Glenmark Pharmaceuticals S.A. Substituted benzo[4,5]furo[3,2-c]pyridine derivatives as PDE 4 inhibitors
US8129401B2 (en) 2004-12-17 2012-03-06 Glenmark Pharmaceuticals S.A. Heterocyclic compounds useful for the treatment of inflammatory and allergic disorders: process for their preparation and pharmaceutical compositions containing them

Also Published As

Publication number Publication date
FR2053028B1 (en) 1974-11-15
NL7008628A (en) 1970-12-29
CH549008A (en) 1974-05-15
CA952913A (en) 1974-08-13
FR2053028A1 (en) 1971-04-16

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Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees