GB1383465A - Glucosamide of 1- p-chlorobenzoyl indolyl-3-acetic acid and processes for its preparation - Google Patents

Glucosamide of 1- p-chlorobenzoyl indolyl-3-acetic acid and processes for its preparation

Info

Publication number
GB1383465A
GB1383465A GB2127873A GB2127873A GB1383465A GB 1383465 A GB1383465 A GB 1383465A GB 2127873 A GB2127873 A GB 2127873A GB 2127873 A GB2127873 A GB 2127873A GB 1383465 A GB1383465 A GB 1383465A
Authority
GB
United Kingdom
Prior art keywords
chlorobenzoyl
glucosamine
reacting
formula
indolyl
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
GB2127873A
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.)
SIR LABO CHIMICO BIOLOGI
Original Assignee
SIR LABO CHIMICO BIOLOGI
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
Priority claimed from IT2039173A external-priority patent/IT1063604B/en
Application filed by SIR LABO CHIMICO BIOLOGI filed Critical SIR LABO CHIMICO BIOLOGI
Publication of GB1383465A publication Critical patent/GB1383465A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
    • 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
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Rheumatology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pain & Pain Management (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Indole Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)

Abstract

1383465 D(+)-glucosamide of 1-(p-chlorobenzoyl) - 2 - methyl - 5 - methoxy indolyl - 3- acetic acid SIR LABORATORI CHIMICO BIOLOGICI SpA 4 May 1973 [9 May 1972 14 Feb 1973] 21278/73 Heading C2C The invention comprises the novel compound of Formula II wherein-NHC 6 H 11 O 5 represents a D( + )-glucosamine residue which may be prepared by (a) reacting D( + )-glucosamine with 1-(p-chlorobenzoyl) - 2 - methyl - 5 - methoxy indolyl - 3- acetic acid chloride in the presence of a base or (b) cyclization of a compound of Formula I wherein NHC 6 H 11 O 5 is again a D(+)-glucosamine residue. 1 - (p - Chlorobenzyl) - 2 - methyl - 5 - methoxy indolyl-3-acetyl chloride is prepared by reaction of the corresponding indolylacetic acid with thionyl chloride. The [N<SP>1</SP> - (p - chlorobenzoyl)] - p - methoxy phenyl hydrazone of N-levulinoyl glucosamine of Formula I is prepared by (a) reacting the [N<SP>1</SP> - (p - chlorobenzoyl)] - p - methoxyphenylhydrazone of levulinic acid with D(+)-glucosamine in the presence of a base or (b) reacting N - levulinoylglucosamine with N<SP>1</SP> - (pmethoxyphenyl) - N<SP>1</SP> - (p - chlorobenzoyl - N<SP>2</SP>- formylhydrazine or (c) reacting N-levulinoylglucosamine with N<SP>1</SP>-(p-chlorobenzoyl)-4-methoxyphenylhydrazine hydrochloride. Pharmaceutical compositions having antiinflammatory activity comprise the compound of Formula I together with an acceptable pharmaceutical excipient.
GB2127873A 1972-05-09 1973-05-04 Glucosamide of 1- p-chlorobenzoyl indolyl-3-acetic acid and processes for its preparation Expired GB1383465A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IT2411872 1972-05-09
IT2039173A IT1063604B (en) 1973-02-14 1973-02-14 Indoleacetic acid d(+) glucosamides - with anti-inflammatory activity

Publications (1)

Publication Number Publication Date
GB1383465A true GB1383465A (en) 1974-02-12

Family

ID=26327513

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2127873A Expired GB1383465A (en) 1972-05-09 1973-05-04 Glucosamide of 1- p-chlorobenzoyl indolyl-3-acetic acid and processes for its preparation

Country Status (9)

Country Link
JP (1) JPS613800B2 (en)
AR (1) AR198471A1 (en)
CA (1) CA980767A (en)
CH (1) CH606072A5 (en)
ES (1) ES414509A1 (en)
FR (1) FR2184033B1 (en)
GB (1) GB1383465A (en)
NL (1) NL179136C (en)
YU (1) YU35267B (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1742534A2 (en) * 2004-04-07 2007-01-17 The University Of Georgia Research Foundation, Inc. Glucosamine and glucosamine/anti-inflammatory mutual prodrugs, compositions, and methods
US8034796B2 (en) 2004-04-07 2011-10-11 The University Of Georgia Research Foundation, Inc. Glucosamine and glucosamine/anti-inflammatory mutual prodrugs, compositions, and methods

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3285908A (en) * 1963-04-30 1966-11-15 Merck & Co Inc Indolyl acid amides

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1742534A2 (en) * 2004-04-07 2007-01-17 The University Of Georgia Research Foundation, Inc. Glucosamine and glucosamine/anti-inflammatory mutual prodrugs, compositions, and methods
EP1742534A4 (en) * 2004-04-07 2011-04-13 Univ Georgia Glucosamine and glucosamine/anti-inflammatory mutual prodrugs, compositions, and methods
US8034796B2 (en) 2004-04-07 2011-10-11 The University Of Georgia Research Foundation, Inc. Glucosamine and glucosamine/anti-inflammatory mutual prodrugs, compositions, and methods
US8361990B2 (en) 2004-04-07 2013-01-29 University Of Georgia Research Foundation, Inc. Glucosamine and glucosamine/anti-inflammatory mutual prodrugs, compositions, and methods

Also Published As

Publication number Publication date
FR2184033A1 (en) 1973-12-21
NL7306501A (en) 1973-11-13
YU122273A (en) 1980-04-30
NL179136B (en) 1986-02-17
CA980767A (en) 1975-12-30
JPS613800B2 (en) 1986-02-04
JPS4966814A (en) 1974-06-28
YU35267B (en) 1980-10-31
CH606072A5 (en) 1978-10-13
AU5506473A (en) 1974-11-07
FR2184033B1 (en) 1976-09-03
NL179136C (en) 1986-07-16
AR198471A1 (en) 1974-06-21
ES414509A1 (en) 1976-07-16

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee