IP Library › Granted Patent US 8,119,690

Granted Patent B2

US 8,119,690 · App. 12/534,439 · Granted Feb 21, 2012

Polyunsaturated fatty acid monoglycerides, derivatives, and uses thereof

Assignee: Centre de Recherche sur les Biotechnologies Marines

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Quick Facts

Patent No.: US 8,119,690
App. No.: 12/534,439
Granted: Feb 21, 2012
Kind: B2

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Abstract

There are provided various polyunsaturated fatty acid monoglycerides and derivatives thereof. These compounds can be useful as cancer chemopreventive agents, cancer treating agent, inhibiting tumor growth or cell proliferation, reducing tumor growth or as radioenhencers for radiotherapy of cancer.

Claims (147)

1. A compound of formula (I), (II), (III), or (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) 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,

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, —C3-C22 alkenyl, or —C3-C22 alkynyl,

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 is chosen from —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, and —C3-C22 alkynyl, and R 2 is chosen from —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, and —C3-C22 alkynyl,

R 1 is chosen from —C(O)NH 3 , —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, and —C3-C22 alkynyl, and R 2 is chosen from —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, and —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;

R 1 is chosen from —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, and —C3-C22 alkynyl, and R 2 is chosen from —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, and —C3-C22 alkynyl,

or a pharmaceutically acceptable salt thereof.

2. The compound of claim 1 , wherein said compound is of formula (I) or (II).

3. The compound of claim 2 , wherein X 1 is O, X 2 is O, and X 3 is O.

4. The compound of claim 3 , wherein R 1 and R 2 each independently represents —H, —C1-C22 alkyl, —C3-C22 alkenyl, or —C3-C22 alkynyl.

5. The compound of claim 3 , wherein R 1 is —H and R 2 is —H.

6. The compound of claim 1 , wherein said compound is of formula (I) and wherein R 1 and R 2 each independently represents —H, —C1-C22 alkyl, —C3-C22 alkenyl, or —C3-C22 alkynyl.

7. The compound of claim 1 , wherein said compound is of formula (II) and wherein R 1 and R 2 each independently represents —H, —C1-C22 alkyl, —C3-C22 alkenyl, or —C3-C22 alkynyl.

8. The compound of claim 1 , wherein said compound is of formula (I) wherein R 1 and R 2 are H.

9. The compound of claim 1 , wherein said compound is of formula (II) wherein R 1 and R 2 are H.

10. The compound of claim 1 , wherein said compound is:

11. The compound of claim 1 , wherein said compound is:

12. The compound of claim 1 , wherein said compound is chosen from:

13. A composition comprising at least two compounds as defined in claim 1 .

14. A composition comprising the compound of claim 10 and:

15. A composition comprising the compound of claim 10 and at least one compound chosen from:

16. A compound of formula (I) or (II):

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 , —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 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, —C1-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 substituent 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,

or a pharmaceutically acceptable salt thereof.

17. The compound of claim 16 , wherein said compound is a compound of formula:

or a pharmaceutically acceptable salt thereof.

18. A compound of formula (I), (II), (III), or (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 , —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 (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

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 substituent 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 (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 it amino acids, —CH 2 OR 5 , —C(O)OR 5 , —C(O)NR 5 , —S(O) 2 NHR 5 , —SOR 5 , —S(O) 2 R 5 , -arylP(O)(OR 5 ) 2 , a sugar, or a sugar phosphate, wherein when R 1 is —H, R 2 is different than —H, and when R 2 is —H, R 1 is different than —H,

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 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;

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)OR 5 , —S(O) 2 NHR 5 , —SOR 5 , —S(O) 2 R 5 , -arylP(O)(OR 5 ) 2 , a sugar, or a sugar phosphate, wherein when R 1 is —H, R 2 is different than —H, and when R 2 is —H, R 1 is different than —H,

R 5 is —H, —C1-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 alkynyi, a three- 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, 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,

or a pharmaceutically acceptable salt thereof.

19. The compound of claim 18 , 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;

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 , —S(O) 2 NHR 5 , —SOR 5 , —S(O) 2 R 5 , -arylP(O)(OR 5 ) 2 , a sugar, or a sugar phosphate, wherein when R 1 is —H, R 2 is different than —H, and when R 2 is —H, R 1 is different than —H;

R 5 is —H, —C1-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) cycloalkyll 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 substituent 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 (IV):

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 , —S(O) 2 NHR 5 , —SOR 5 , —S(O) 2 R 5 , -arylP(O)(OR 5 ) 2 , a sugar, or a sugar phosphate, wherein when R 1 is —H, R 2 is different than —H, and when R 2 is —H, R 1 is different than —H;

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

20. The compound of claim 18 , 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;

in formula (II):

X 1 is O, NH, or S;

X 2 is O, NH, or S;

X 3 is O, NH, or S;

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, —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, 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

21. The compound of claim 18 , wherein said 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 023076/0594 →

Continuity (3)

Continuation In Part PCTCA2008000301 · Feb 14, 2008

Provisional Application 60889984 · Feb 15, 2007

Related Publication 20090292019A1 · Nov 26, 2009