Process for the manufacture of ajoene derivatives

Thomas Bjarnsholt; Niels Hoeiby,; Peter Østrup Jensen; Richard Phipps; Sundaram Shanmugham, Meenakshi; Maria Alhede; Louise Dahl Hultqvist; Tim Holm Jakobsen; David Tanner; Ostenfeld Larsen, Thomas; Michael Givskov,

Process for the manufacture of ajoene derivatives

Thomas Bjarnsholt (Inventor), Niels Hoeiby, (Inventor), Peter Østrup Jensen (Inventor), Richard Phipps (Inventor), Sundaram Shanmugham, Meenakshi (Inventor), Maria Alhede (Inventor), Louise Dahl Hultqvist (Inventor), Tim Holm Jakobsen (Inventor), David Tanner (Inventor), Ostenfeld Larsen, Thomas (Inventor), Michael Givskov, (Inventor)

Research output: Patent

Abstract

The present invention relates to the compound (E,Z)-ajoene of formula (1) for use in treatment of bacterial infections. Another aspect of the present invention is a composition comprising (E,Z)-ajoene of formula (1) and at least one antibiotic. Yet another aspect of the invention relates to a method for manufacturing (E,Z) ajoene of formula (1) wherein the conformation of the internal C=C- bond can be either E or Z or a mixture thereof, said method comprising reacting allicin of formula (3) with an acid in the presence of a solvent to provide (E,Z ajoene) of formula (1) as defined above. Yet another aspect of the invention is (E,Z)-ajoene of formula 1 obtainable by the method described above.

Original language	English
IPC	C07C 323/ 65 A I
Patent number	WO2012076016
Country/Territory	Denmark
Priority date	08/12/2010
Priority number	EP20100194154
Publication status	Published - 14 Jun 2012

Cite this

Process for the manufacture of ajoene derivatives. / Bjarnsholt, Thomas (Inventor); Hoeiby, Niels (Inventor); Jensen, Peter Østrup (Inventor); Phipps, Richard (Inventor); Shanmugham, Meenakshi, Sundaram (Inventor); Alhede, Maria (Inventor); Hultqvist, Louise Dahl (Inventor); Jakobsen, Tim Holm (Inventor); Tanner, David (Inventor); Larsen, Thomas, Ostenfeld (Inventor); Givskov, Michael (Inventor).

Patent No.: WO2012076016. Jun 14, 2012.

Research output: Patent

Bjarnsholt, Thomas (Inventor) ; Hoeiby, Niels (Inventor) ; Jensen, Peter Østrup (Inventor) ; Phipps, Richard (Inventor) ; Shanmugham, Meenakshi, Sundaram (Inventor) ; Alhede, Maria (Inventor) ; Hultqvist, Louise Dahl (Inventor) ; Jakobsen, Tim Holm (Inventor) ; Tanner, David (Inventor) ; Larsen, Thomas, Ostenfeld (Inventor) ; Givskov, Michael (Inventor). / Process for the manufacture of ajoene derivatives. Patent No.: WO2012076016. Jun 14, 2012.

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title = "Process for the manufacture of ajoene derivatives",

abstract = "The present invention relates to the compound (E,Z)-ajoene of formula (1) for use in treatment of bacterial infections. Another aspect of the present invention is a composition comprising (E,Z)-ajoene of formula (1) and at least one antibiotic. Yet another aspect of the invention relates to a method for manufacturing (E,Z) ajoene of formula (1) wherein the conformation of the internal C=C- bond can be either E or Z or a mixture thereof, said method comprising reacting allicin of formula (3) with an acid in the presence of a solvent to provide (E,Z ajoene) of formula (1) as defined above. Yet another aspect of the invention is (E,Z)-ajoene of formula 1 obtainable by the method described above.",

author = "Thomas Bjarnsholt and Niels Hoeiby, and Jensen, {Peter {\O}strup} and Richard Phipps and {Shanmugham, Meenakshi}, Sundaram and Maria Alhede and Hultqvist, {Louise Dahl} and Jakobsen, {Tim Holm} and David Tanner and {Larsen, Thomas}, Ostenfeld and Michael Givskov,",

year = "2012",

month = jun,

day = "14",

language = "English",

type = "Patent",

note = "WO2012076016; C07C 323/ 65 A I",

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TY - PAT

T1 - Process for the manufacture of ajoene derivatives

AU - Bjarnsholt, Thomas

AU - Hoeiby,, Niels

AU - Jensen, Peter Østrup

AU - Phipps, Richard

AU - Shanmugham, Meenakshi, Sundaram

AU - Alhede, Maria

AU - Hultqvist, Louise Dahl

AU - Jakobsen, Tim Holm

AU - Tanner, David

AU - Larsen, Thomas, Ostenfeld

AU - Givskov,, Michael

PY - 2012/6/14

Y1 - 2012/6/14

N2 - The present invention relates to the compound (E,Z)-ajoene of formula (1) for use in treatment of bacterial infections. Another aspect of the present invention is a composition comprising (E,Z)-ajoene of formula (1) and at least one antibiotic. Yet another aspect of the invention relates to a method for manufacturing (E,Z) ajoene of formula (1) wherein the conformation of the internal C=C- bond can be either E or Z or a mixture thereof, said method comprising reacting allicin of formula (3) with an acid in the presence of a solvent to provide (E,Z ajoene) of formula (1) as defined above. Yet another aspect of the invention is (E,Z)-ajoene of formula 1 obtainable by the method described above.

AB - The present invention relates to the compound (E,Z)-ajoene of formula (1) for use in treatment of bacterial infections. Another aspect of the present invention is a composition comprising (E,Z)-ajoene of formula (1) and at least one antibiotic. Yet another aspect of the invention relates to a method for manufacturing (E,Z) ajoene of formula (1) wherein the conformation of the internal C=C- bond can be either E or Z or a mixture thereof, said method comprising reacting allicin of formula (3) with an acid in the presence of a solvent to provide (E,Z ajoene) of formula (1) as defined above. Yet another aspect of the invention is (E,Z)-ajoene of formula 1 obtainable by the method described above.

M3 - Patent

M1 - WO2012076016

ER -