WO2006014549A8 - Synthesis of azo bonded immunoregulatory compounds - Google Patents

Synthesis of azo bonded immunoregulatory compounds

Info

Publication number
WO2006014549A8
WO2006014549A8 PCT/US2005/024109 US2005024109W WO2006014549A8 WO 2006014549 A8 WO2006014549 A8 WO 2006014549A8 US 2005024109 W US2005024109 W US 2005024109W WO 2006014549 A8 WO2006014549 A8 WO 2006014549A8
Authority
WO
WIPO (PCT)
Prior art keywords
suitably functionalized
alkyl
methods
group
aniline compound
Prior art date
Application number
PCT/US2005/024109
Other languages
French (fr)
Other versions
WO2006014549A3 (en
WO2006014549A2 (en
Inventor
Jennifer A Riggs Sauthier
Nnochiri N Ekwuribe
Original Assignee
Nobex Corp
Jennifer A Riggs Sauthier
Nnochiri N Ekwuribe
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 Nobex Corp, Jennifer A Riggs Sauthier, Nnochiri N Ekwuribe filed Critical Nobex Corp
Priority to PL05769456T priority Critical patent/PL1773767T3/en
Priority to EP05769456.4A priority patent/EP1773767B1/en
Priority to ES05769456.4T priority patent/ES2565848T3/en
Priority to DK05769456.4T priority patent/DK1773767T3/en
Priority to US11/631,582 priority patent/US7932366B2/en
Publication of WO2006014549A2 publication Critical patent/WO2006014549A2/en
Publication of WO2006014549A3 publication Critical patent/WO2006014549A3/en
Publication of WO2006014549A8 publication Critical patent/WO2006014549A8/en
Priority to US13/094,135 priority patent/US8314214B2/en
Priority to US13/680,434 priority patent/US8754197B2/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
    • C07C245/02—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides
    • C07C245/06—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings
    • C07C245/08—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings with the two nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings, e.g. azobenzene

Abstract

Methods are disclosed for preparing compounds of Formula I: where R1, R3, and R4 are independently hydrogen or C1 to C4 alkyl, and R2 is: where R5 is selected from the group consisting of hydrogen and C1 to C4 alkyl, or where R6, R7 and R8 are independently hydrogen or C1 to C4 alkyl; or the esters or pharmacologically acceptable salts thereof.. The methods can involve converting a suitably functionalized aniline compound to a diazonium salt (which aniline compound can be first formed by reduction of a nitrobenzene) and coupling the diazonium salt with a suitably functionalized benzene compound. The suitably functionalized aniline compound either includes a primary alcohol or aldehyde group, which is then oxidized to a carboxylic acid group, or includes a nitrile or amide group, which is hydrolyzed to a carboxylic acid group. The methods can also involve the direct coupling (via reduction of nitro groups to form an azo linkage) of suitably functionalized nitrobenzenes. The compounds and or their metabolites can be used to treat or prevent various diseases, particularly inflammatory conditions of the GI tract.
PCT/US2005/024109 2004-07-07 2005-07-07 Synthesis of azo bonded immunoregulatory compounds WO2006014549A2 (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
PL05769456T PL1773767T3 (en) 2004-07-07 2005-07-07 Synthesis of azo bonded immunoregulatory compounds
EP05769456.4A EP1773767B1 (en) 2004-07-07 2005-07-07 Synthesis of azo bonded immunoregulatory compounds
ES05769456.4T ES2565848T3 (en) 2004-07-07 2005-07-07 Synthesis of immunoregulatory compounds bound by azo groups
DK05769456.4T DK1773767T3 (en) 2004-07-07 2005-07-07 Synthesis of azo bound in immune regulatory relations
US11/631,582 US7932366B2 (en) 2004-07-07 2005-07-07 Synthesis of azo bonded immunoregulatory compounds
US13/094,135 US8314214B2 (en) 2004-07-07 2011-04-26 Synthesis of azo bonded immunoregulatory compounds
US13/680,434 US8754197B2 (en) 2004-07-07 2012-11-19 Synthesis of azo bonded immunoregulatory compounds

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US58599504P 2004-07-07 2004-07-07
US60/585,995 2004-07-07

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US11/631,582 A-371-Of-International US7932366B2 (en) 2004-07-07 2005-07-07 Synthesis of azo bonded immunoregulatory compounds
US13/094,135 Division US8314214B2 (en) 2004-07-07 2011-04-26 Synthesis of azo bonded immunoregulatory compounds

Publications (3)

Publication Number Publication Date
WO2006014549A2 WO2006014549A2 (en) 2006-02-09
WO2006014549A3 WO2006014549A3 (en) 2006-05-26
WO2006014549A8 true WO2006014549A8 (en) 2007-02-22

Family

ID=35787649

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2005/024109 WO2006014549A2 (en) 2004-07-07 2005-07-07 Synthesis of azo bonded immunoregulatory compounds

Country Status (7)

Country Link
US (3) US7932366B2 (en)
EP (1) EP1773767B1 (en)
DK (1) DK1773767T3 (en)
ES (1) ES2565848T3 (en)
HU (1) HUE028158T2 (en)
PL (1) PL1773767T3 (en)
WO (1) WO2006014549A2 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8048924B2 (en) * 2001-08-29 2011-11-01 Biocon Limited Methods and compositions employing 4-aminophenylacetic acid compounds

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