IP Library › Granted Patent US 8,222,295

Granted Patent B2

US 8,222,295 · App. 12/535,990 · Granted Jul 17, 2012

Compositions comprising polyunsaturated fatty acid monoglycerides or derivatives thereof and uses thereof

Assignee: Centre de Recherche sur les Biotechnologies Marines

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Quick Facts

Patent No.: US 8,222,295
App. No.: 12/535,990
Granted: Jul 17, 2012
Kind: B2

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Abstract

There are provided various compounds and compositions comprising polyunsaturated fatty acid monoglycerides and derivatives thereof. These compounds and compositions can be useful as cancer chemopreventive agents. They can also be useful for enhancing solubility of various active agents and enhancing their bioavailability.

Claims (193)

1. A composition comprising at least one compound chosen from compounds of formulae (I), (II), (III), and (IV):

wherein

in formula (I):

X 1 is O, NH, or S;

X 2 is O, NH, or S;

X 3 is O, NH, or S;

R 1 and R 2 each independently represents —H, —C(O)NH 2 , —S(O)NH 2 , —S(O) 2 NH 2 , —C1-C22 (oxy)alkyl, —C1-C22 alkyl, —C1-C22 (hydroxy)alkyl, —C1-C22 (amino)alkyl, —C1-C22 (halo)alkyl, —C3-C22 alkenyl, —C3-C22 alkynyl, —(C3-C7) cycloalkyl unsubstituted or substituted with at least one substituent chosen from C1-C22 alkyl, —C2-C22 alkenyl, and —C2-C22 alkynyl, —C6-C12 aryl, —C7-C22 (aryl)alkyl, —C8-C22 (aryl)alkenyl, —C8-C22 (aryl)alkynyl, three- to seven-membered non-aromatic heterocycle unsubstituted or substituted with at least one substituent chosen from —C1-C22 alkyl, —C2-C22 alkenyl, and —C2-C22 alkynyl, five- to seven-membered aromatic heterocycle unsubstituted or substituted with at least one substituent chosen from —C1-C22 alkyl, —C2-C22 alkenyl, and —C2-C22 alkynyl, —(CH 2 ) n amino acid wherein the amino acid is connected through its alpha carbon atom, —(CH 2 ) n peptide wherein the peptide is connected through the alpha carbon atom of one of its amino acids, —CH 2 OR 5 , —C(O)OR 5 , —C(O)NR 5 , —P(O)(OR 5 ) 2 , —S(O) 2 NHR 5 , —SOR 5 , —S(O)R 5 , —arylP(O)(OR 5 ) 2 , a sugar, or a sugar phosphate

or R 1 and R 2 are joined together so as to form a five- to seven-membered non-aromatic heterocycle unsubstituted or substituted with at least one substituent chosen from —C1-C22 alkyl, —C2-C22 alkenyl, and —C2-C22 alkynyl, a phosphate, sulfate carbonyl group, or a thiocarbonyl imine;

R 5 is —H, —C 1 -C22 alkyl, —(C3-C7) cycloalkyl, —C1-C22 (halo)alkyl, —C6-C12 aryl, —C2-C22 alkenyl, —C2-C22 alkynyl, —C7-C22 (aryl)alkyl, —C8-C22 (aryl)alkenyl, —C8-C22 (aryl)alkynyl, —C1-C22 (hydroxy)alkyl, —C1-C22 alkoxy, —C1-C22 (amino)alkyl, a —(C3-C7) cycloalkyl unsubstituted or substituted with at least one substituent chosen from —C1-C22 alkyl, —C2-C22 alkenyl, and —C2-C22 alkynyl, a three- to seven-membered non-aromatic heterocycle unsubstituted or substituted at least one substituent chosen from —C1-C22 alkyl, —C2-C22 alkenyl, and —C2-C22 alkynyl, a three- to seven-membered aromatic heterocycle unsubstituted or substituted with at least one susbtituent chosen from —C1-C22 alkyl, —C2-C22 alkenyl, and —C2-C22 alkynyl, a —(CH 2 ) n amino acid wherein the amino acid is connected to the compound through its alpha carbon atom, a —(CH 2 ) n peptide wherein the peptide is connected to the compound through the alpha carbon atom of one of its amino acids, a sugar or a sugar phosphate; and

n is an integer having a value of 0, 1, 2, 3, or 4,

in formula (II):

X 1 is O, NH, or S;

X 2 is O, NH, or S;

X 3 is O, NH, or S;

R 1 and R 2 each independently represents —H, —C(O)NH 2 , —S(O)NH 2 , —S(O) 2 NH 2 , —C1-C22 (oxy)alkyl, —C1-C22 alkyl, —C1-C22 (hydroxy)alkyl, —C1-C22 (amino)alkyl, —C1-C22 (halo)alkyl, —C3-C22 alkenyl, —C3-C22 alkynyl, —(C3-C7) cycloalkyl unsubstituted or substituted with at least one substituent chosen from C1-C22 alkyl, —C2-C22 alkenyl, and —C2-C22 alkynyl, —C6-C12 aryl, —C7-C22 (aryl)alkyl, —C8-C22 (aryl)alkenyl, —C8-C22 (aryl)alkynyl, three- to seven-membered non-aromatic heterocycle unsubstituted or substituted with at least one substituent chosen from —C1-C22 alkyl, —C2-C22 alkenyl, and —C2-C22 alkynyl, five- to seven-membered aromatic heterocycle unsubstituted or substituted with at least one substituent chosen from —C1-C22 alkyl, —C2-C22 alkenyl, and —C2-C22 alkynyl, —(CH 2 ) n amino acid wherein the amino acid is connected through its alpha carbon atom, —(CH 2 ) n peptide wherein the peptide is connected through the alpha carbon atom of one of its amino acids, —CH 2 OR 5 , —C(O)OR 5 , —C(O)NR 5 , —P(O)(OR 5 ) 2 , —S(O) 2 NHR 5 , —SOR 5 , —S(O) 2 R 5 , -arylP(O)(OR 5 ) 2 , a sugar, or a sugar phosphate

n is an integer having a value of 0, 1, 2, 3, or 4,

in formula (III)

X 1 is O, NH, or S;

X 2 is O, NH, or S;

X 3 is O, NH, or S;

R 1 and R 2 each independently represents, —H, —C(O)NH 2 , —S(O)NH 2 , —S(O) 2 NH 2 , —C1-C22 (oxy)alkyl, —C1-C22 alkyl, —C1-C22 (hydroxy)alkyl, —C1-C22 (amino)alkyl, —C1-C22 (halo)alkyl, —C3-C22 alkenyl, —C3-C22 alkynyl, —(C3-C7) cycloalkyl unsubstituted or substituted with at least one substituent chosen from C1-C22 alkyl, —C2-C22 alkenyl, and —C2-C22 alkynyl, —C6-C12 aryl, —C7-C22 (aryl)alkyl, —C8-C22 (aryl)alkenyl, —C8-C22 (aryl)alkynyl, three- to seven-membered non-aromatic heterocycle unsubstituted or substituted with at least one substituent chosen from —C1-C22 alkyl, —C2-C22 alkenyl, and —C2-C22 alkynyl, five- to seven-membered aromatic heterocycle unsubstituted or substituted with at least one substituent chosen from —C1-C22 alkyl, —C2-C22 alkenyl, and —C2-C22 alkynyl, —(CH 2 ) n amino acid wherein the amino acid is connected through its alpha carbon atom, —(CH 2 ) n peptide wherein the peptide is connected through the alpha carbon atom of one of its amino acids, —CH 2 OR 5 , —C(O)OR 5 , —C(O)NR 5 , —P(O)(OR 5 ) 2 , —S(O) 2 NHR 5 , —SOR 5 , —S(O) 2 R 5 , -arylP(O)(OR 5 ) 2 , a sugar, or a sugar phosphate,

or R 1 and R 2 are joined together so as to form a five- to seven-membered non-aromatic heterocycle comprising at least one hetero atom chosen from nitrogen, oxygen, and sulfur, said heterocyle being unsubstituted or substituted with at least one substituent chosen from —C1-C22 alkyl, —C2-C22 alkenyl, and —C2-C22 alkynyl, a phosphate, sulfate carbonyl group, or a thiocarbonyl imine;

n is an integer having a value of 0, 1, 2, 3, or 4,

in formula (IV)

X 1 is O, NH, or S;

X 2 is O, NH, or S;

X 3 is O, NH, or S;

n is an integer having a value of 0, 1, 2, 3, or 4,

or a pharmaceutically acceptable salt thereof:

and

at least one active agent chosen from a turmeric crude extract or purified extract from turmeric crude extract, curcumin, artemisinin, artemisia crude extract or purified extract from artemisia crude extract, green lipped mussels crude extract or purified extract from green lipped mussels crude extract, microalage crude extract or purified extract of a microalgae, astaxanthin, lutein, zeaxanthin, and mixtures thereof.

2. The composition of claim 1 , wherein said at least one active agent is chosen from a turmeric crude extract or purified extract from turmeric crude extract, curcumin, and mixtures thereof.

3. The composition of claim 2 , wherein said at least one compound is chosen from:

4. The composition of claim 2 , wherein said at least one compound is chosen from:

5. The composition of claim 2 , wherein said at least one compound is chosen from:

6. The composition of claim 1 , wherein

in formula (I):

X 1 is O, NH, or S;

X 2 is O, NH, or S;

X 3 is O, NH, or S; and

R 1 and R 2 each independently represents —H, —C(O)NH 2 , —S(O) 2 NH 2 , —C1-C22 (oxy)alkyl, —C1-C22 alkyl, —C1-C22 (hydroxy)alkyl, —C1-C22 (amino)alkyl, —C3-C22 alkenyl, or —C3-C22 alkynyl,

in formula (II):

X 1 is O, NH, or S;

X 2 is O, NH, or S;

X 3 is O, NH, or S; and

in formula (III):

X 1 is O, NH, or S;

X 2 is O, NH, or S;

X 3 is O, NH, or S; and

R 1 and R 2 each independently represents —H, —C(O)NH 2 , —S(O) 2 NH 2 , —C1-C22 (oxy)alkyl; —C1-C22 alkyl, —C1-C22 (hydroxy)alkyl, —C1-C22 (amino)alkyl, —C3-C22 alkenyl, or —C3-C22 alkynyl,

in formula (IV):

X 1 is O, NH, or S;

X 2 is O, NH, or S;

X 3 is O, NH, or S; and

7. The composition of claim 2 , wherein:

in formula (I):

X 1 is O, NH, or S;

X 2 is O, NH, or S;

X 3 is O, NH, or S; and

in formula (II):

X 1 is O, NH, or S;

X 2 is O, NH, or S;

X 3 is O, NH, or S; and

in formula (III):

X 1 is O, NH, or S;

X 2 is O, NH, or S;

X 3 is O, NH, or S; and

in formula (IV):

X 1 is O, NH, or S;

X 2 is O, NH, or S;

X 3 is O, NH, or S; and

8. The composition of claim 1 , wherein said at least one compound is chosen from compounds of formulae (III), and (IV), in which

in formula (III):

X 1 is O, NH, or S;

X 2 is O, NH, or S;

X 3 is O, NH, or S; and

in formula (IV):

X 1 is O, NH, or S;

X 2 is O, NH, or S;

X 3 is O, NH, or S; and

9. The composition of claim 2 , wherein said at least one compound is chosen from compounds of formulae (III), and (IV), in which

in formula (III):

X 1 is O, NH, or S;

X 2 is O, NH, or S;

X 3 is O, NH, or S; and

in formula (IV):

X 1 is O, NH, or S;

X 2 is O, NH, or S;

X 3 is O, NH, or S; and

10. The composition of claim 1 , wherein said at least one compound is a compound of formula (III), in which

X 1 is O, NH, or S;

X 2 is O, NH, or S;

X 3 is O, NH, or S; and

11. The composition of claim 2 , wherein said at least one compound is a compound of formula (III), in which

X 1 is O, NH, or S;

X 2 is O, NH, or S;

X 3 is O, NH, or S; and

12. The composition of claim 1 , wherein said at least one active agent is curcumin.

13. The composition of claim 1 , wherein said at least one active agent is a turmeric crude extract or purified extract from turmeric crude extract.

14. The composition of claim 12 , wherein said at least one compound is:

15. The composition of claim 12 , wherein

in formula (I):

X 1 is O, NH, or S;

X 2 is O, NH, or S;

X 3 is O, NH, or S; and

in formula (II):

X 1 is O, NH, or S;

X 2 is O, NH, or S;

X 3 is O, NH, or S; and

in formula (III):

X 1 is O, NH, or S;

X 2 is O, NH, or S;

X 3 is O, NH, or S; and

in formula (IV):

X 1 is O, NH, or S;

X 2 is O, NH, or S;

X 3 is O, NH, or S; and

16. The composition of claim 13 , wherein

in formula (I):

X 1 is O, NH, or S;

X 2 is O, NH, or S;

X 3 is O, NH, or S; and

in formula (II):

X 1 is O, NH, or S;

X 2 is O, NH, or S;

X 3 is O, NH, or S; and

in formula (III):

X 1 is O, NH, or S;

X 2 is O, NH, or S;

X 3 is O, NH, or S; and

in formula (IV):

X 1 is O, NH, or S;

X 2 is O, NH, or S;

X 3 is O, NH, or S; and

17. The composition of claim 12 , wherein said at least one compound is chosen from compounds of formulae (III), and (IV), in which

in formula (III):

X 1 is O, NH, or S;

X 2 is O, NH, or S;

X 3 is O, NH, or S; and

in formula (IV):

X 1 is O, NH, or S;

X 2 is O, NH, or S;

X 3 is O, NH, or S; and

18. The composition of claim 13 , wherein said at least one compound is chosen from compounds of formulae (III), and (IV), in which

in formula (III):

X 1 is O, NH, or S;

X 2 is O, NH, or S;

X 3 is O, NH, or S; and

in formula (IV):

X 1 is O, NH, or S;

X 2 is O, NH, or S;

X 3 is O, NH, or S; and

19. The composition of claim 12 , wherein said at least one compound is a formula (III), in which

X 1 is O, NH, or S;

X 2 is O, NH, or S;

X 3 is O, NH, or S; and

20. The composition of claim 13 , wherein said at least one compound is a compound of formulae (III), in which

X 1 is O, NH, or S;

X 2 is O, NH, or S;

X 3 is O, NH, or S; and

21. The composition of claim 12 , wherein said at least one compound is:

Assignments (2)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 6, 2017

From: CENTRE DE RECHERCHE SUR LES BIOTECHNOLOGIES MARINES

To: SCF PHARMA INC.

Reel/Frame 043494/0442 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 11, 2009

From: FORTIN, SAMUEL

To: CENTRE DE RECHERCHE SUR LES BIOTECHNOLOGIES MARINES

Reel/Frame 023080/0093 →

Continuity (3)

Continuation In Part PCTCA2008000530 · Mar 19, 2008

Provisional Application 60895795 · Mar 20, 2007

Related Publication 20090291102A1 · Nov 26, 2009