GB1453885A - Cyctopenla-j,k-phenanthren-4-yl alkanoic acids and their derivatives - Google Patents

Cyctopenla-j,k-phenanthren-4-yl alkanoic acids and their derivatives

Info

Publication number
GB1453885A
GB1453885A GB1857874A GB1857874A GB1453885A GB 1453885 A GB1453885 A GB 1453885A GB 1857874 A GB1857874 A GB 1857874A GB 1857874 A GB1857874 A GB 1857874A GB 1453885 A GB1453885 A GB 1453885A
Authority
GB
United Kingdom
Prior art keywords
hydrogen
prepared
alkyl
iodo
acids
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
GB1857874A
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 GB1453885A publication Critical patent/GB1453885A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen 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]
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
    • C07C49/697—Unsaturated compounds containing a keto groups being part of a ring containing halogen containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
    • C07C49/747—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
    • C07C49/755—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups a keto group being part of a condensed ring system with two or three rings, at least one ring being a six-membered aromatic ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pain & Pain Management (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Rheumatology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1453885 Cyclopenta[j, k]pheranthren-4-ylalkanoic acids and derivatives MERCK & CO Inc 29 April 1974 [4 May 1973] 18578/74 Heading C2C Novel compounds I in which each of R 1 and R 2 is hydrogen or alkyl; R 3 is hydrogen, alkyl, halogen, halogenated alkyl, phenyl, alkylthio, phenylthio, alkenyl, alkoxyphenyl or benzyl; R 4 , R 5 and R 6 are each hydrogen, halogen, alkyl, acyloxy, alkoxy, benzyloxy, halogenated benzyloxy, (C 1-5 alkyl)-benzyloxy, acylamino, alkylamino, dialkylamino, dialkylaminoalkyl, sulfamoyl, alkylthio, mercapto, hydroxy, hydroxyalkyl, alkenyl, alkenyloxy, alkylsulfinyl, alkylsulfonyl, dialkylsulfamoyl, carboxyl, carbalkoxy, carbamido, cyano, halogenated alkyl, cycloalkyl, phenyl, benzyl, benzylthio, phenoxy or cycloalkoxy, or R 5 is joined to R 6 to form a methylenedioxy radical and R 4 is hydrogen or R 5 is joined to R 4 to form a butadienylene radical and R 6 is hydrogen; R 7 is hydrogen, halogen, methyl, alkylthio, alkenylsulfinyl or alkylsulfonyl; R 8 is hydrogen, halogen, hydroxy, alkoxy, haloalkyl, phenyl, alkanoylamino or alkanoyl; and M is hydroxy, C 1-5 alkoxy, C 2-5 alkenyloxy, phenoxy, substituted C 1-5 alkoxy, amino, alkylamino, dialkylamino, N-morpholino, hydroxyalkylamino, polyhydroxyalkylamino, dialkylaminoalkylamino, aminoalkylamino, #- D - glucopyranuronyloxy, benzylamino, phenethylamino, (benzyloxycarbonylmethyl)amino, carboxymethylamino, 1 - piperidinyl, 1 - pyrrolidinyl, 1 - piperazinyl, 4 - methyl - 1 - piperazinyl, 4 - phenyl - 1 - piperazinyl, 4 - (2 - hydroxyethyl) - 1 - piperazinyl, 2 - hydroxyethylamino, 2 - ethoxyethylamino, di - (#- ethoxyethyl)amino, anilino, p - ethoxyanilino, p - chloroanilino, p - fluoroanilino, p - trifluoromethylanilino, cyclohexylamino, D- glucosamino, tetra - O - acetyl - D - glucosamino, D - galactosylamino, D - mannosylamino, D - mannosamino, or the group OMe, in which Me is a cation, or are anhydrides of the acids are prepared by cyclizing a compound II and if desired hydrolysing an ester to the free acid and forming an ester, amide or anhydride derivative from the free acid by known methods. Compounds II (M=OCH 3 , R 1 =H and R 1 = H or Me) are prepared by condensing a corresponding 7-iodo-3-indenyl-aliphatic acid with an R 7 , R 8 substituted 2-iodobenzaldehyde. The 2-iodobenzaldehydes are prepared by diazotization of an anthranilic acid and reaction with KI to produce the corresponding 2-iodobenzoic acid which is reduced to the aldehyde. Substituted anthranilic acids are prepared by reduction of 2-nitrobenzoic acids. 4-Methylthio- 2-nitrobenzoic acid is prepared reacting the corresponding 4-chloro compound with MeSH. The 7 - iodo - 3 - indenyl - acetic and α -(7- iodo-3-indenyl)propionic acids are prepared by reacting a 4-iodo-indanone with an α-bromoacetate or propionate followed by dehydration. 4-Iodo-indanones are prepared by nitration using KNO 2 or NaNO 2 at the 4-position of an indanone, reduction to the amino group and diazotization followed by treatment with KI. Compounds I have anti-inflammatory, analgesic and anti-pyretic activity and form with a carrier a pharmaceutical composition which may be administered orally, parenterally, rectally or topically.
GB1857874A 1973-05-04 1974-04-29 Cyctopenla-j,k-phenanthren-4-yl alkanoic acids and their derivatives Expired GB1453885A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US357314A US3867433A (en) 1973-05-04 1973-05-04 Cyclopenta{8 j,k{9 -phenanthrene-4-acetic acids and related compounds

Publications (1)

Publication Number Publication Date
GB1453885A true GB1453885A (en) 1976-10-27

Family

ID=23405100

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1857874A Expired GB1453885A (en) 1973-05-04 1974-04-29 Cyctopenla-j,k-phenanthren-4-yl alkanoic acids and their derivatives

Country Status (7)

Country Link
US (1) US3867433A (en)
JP (1) JPS5013371A (en)
CH (1) CH592597A5 (en)
DE (1) DE2421541A1 (en)
FR (1) FR2236488B1 (en)
GB (1) GB1453885A (en)
NL (1) NL7405118A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6777575B2 (en) 1997-07-07 2004-08-17 Rhone-Poulenc Agro Process for the preparation of 2-alkylthio benzoic acid derivatives

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4704467A (en) * 1986-12-12 1987-11-03 Stauffer Chemical Company Method for preparation of mercaptobenzoates
US4692545A (en) * 1986-12-12 1987-09-08 Stauffer Chemical Company Method for preparation of mercaptobenzoates
MX168606B (en) * 1986-12-12 1993-06-01 Ici American Ine METHOD FOR THE PREPARATION OF MERCAPTOBENZOATES.
US6180629B1 (en) 1998-08-14 2001-01-30 Cell Pathways, Inc. [4,5]-Fused-1,3-disubstituted-1,2-diazine-6-one derivatives with nitrogen containing substitutents in position one for the treatment of neoplasia

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB330916A (en) * 1929-02-01 1930-06-19 Ig Farbenindustrie Ag Manufacture of aryl-acetic acids and substitution products thereof
US3654349A (en) * 1970-05-01 1972-04-04 Merck & Co Inc Substituted indenyl acetic acids
US3766259A (en) * 1970-05-01 1973-10-16 Merck & Co Inc Preparation of 1-aryl-3-indenyl acetic acids

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6777575B2 (en) 1997-07-07 2004-08-17 Rhone-Poulenc Agro Process for the preparation of 2-alkylthio benzoic acid derivatives

Also Published As

Publication number Publication date
US3867433A (en) 1975-02-18
CH592597A5 (en) 1977-10-31
DE2421541A1 (en) 1974-11-21
FR2236488B1 (en) 1978-02-03
FR2236488A1 (en) 1975-02-07
NL7405118A (en) 1974-11-06
JPS5013371A (en) 1975-02-12

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee