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
Grant status
Application
Patent type
Prior art keywords
sp
gt
lt
chlorobenzoyl
glucosamine
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
SIR LABORATORI CHEMICO BIOLOGICI SpA
Original Assignee
SIR LABO CHIMICO BIOLOGI
SIR LABORATORI CHEMICO BIOLOGICI SpA
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

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/26Acyclic or carbocyclic radicals, substituted by hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D209/00Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04Indoles; Hydrogenated indoles
    • C07D209/10Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring

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)

Priority Applications (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 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 (6)

Country Link
JP (1) JPS613800B2 (en)
CA (1) CA980767A (en)
ES (1) ES414509A1 (en)
FR (1) FR2184033B1 (en)
GB (1) GB1383465A (en)
NL (1) NL179136C (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 Type
JPS613800B2 (en) 1986-02-04 grant
NL179136C (en) 1986-07-16 grant
NL7306501A (en) 1973-11-13 application
CA980767A (en) 1975-12-30 grant
NL179136B (en) 1986-02-17 application
ES414509A1 (en) 1976-07-16 application
JPS4966814A (en) 1974-06-28 application
FR2184033A1 (en) 1973-12-21 application
FR2184033B1 (en) 1976-09-03 grant
CA980767A1 (en) grant

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Legal Events

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