Back to results
US 2009/0291102 A1Published application
Compositions comprising polyunsaturated fatty acid monoglycerides or derivatives thereof and uses thereof
AssigneeCentre de Recherche sur les Biotechnologies Marines
InventorSamuel FORTIN
Life of this patent
Estimating the term…
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.
Claims20
A composition comprising at least one active agent and at least one compound chosen from compounds of formulae (I), (II), (III), and (IV):
- wherein
- in formula (I):
- X1 is O, NH, or S;
- X2 is O, NH, or S;
- X3 is O, NH, or S;
- R1 and R2 each independently represents —H, —C(O)NH2, —S(O)2NH2, —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):
- X1 is O, NH, or S;
- X2 is O, NH, or S;
- X3 is O, NH, or S;
- R1 and R2 each independently represents —H, —C(O)NH2, —S(O)NH2, —S(O)2NH2, —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)
- X1 is O, NH, or S;
- X2 is O, NH, or S;
- X3 is O, NH, or S;
- R1 is chosen from —H, —C(O)NH2, —S(O)NH2, —S(O)2NH2, -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 R2 is chosen from —C(O)NH2, —S(O)NH2, —S(O)2NH2, —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
- R1 is chosen from —C(O)NH2, —S(O)NH2, —S(O)2NH2, —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 R2 is chosen from —H, —C(O)NH2, —S(O)NH2, —S(O)2NH2, —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)
- X1 is O, NH, or S;
- X2 is O, NH, or S;
- X3 is O, NH, or S;
- R1 is chosen from —H, —C(O)NH2, —S(O)NH2, —S(O)2NH2, -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 R2 is chosen from —C(O)NH2, —S(O)NH2, —S(O)2NH2, —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
- R1 is chosen from —C(O)NH2, —S(O)NH2, —S(O)2NH2, —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 R2 is chosen from —H, —C(O)NH2, —S(O)NH2, —S(O)2NH2, —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.
23 more elements
A composition comprising at least one compound chosen from compounds of formulae (I), (II), (III), and (IV):
- wherein
- in formula (I):
- X1 is O, NH, or S;
- X2 is O, NH, or S;
- X3 is O, NH, or S;
- R1 and R2 each independently represents —H, —C(O)NH2, —S(O)NH2, —S(O)2NH2, —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, —(CH2)namino acid wherein the amino acid is connected through its alpha carbon atom, —(CH2)npeptide wherein the peptide is connected through the alpha carbon atom of one of its amino acids, —CH2OR5, —C(O)OR5, —C(O)NR5, —P(O)(OR5)2, —S(O)2NHR5, —SOR5, —S(O)2R5, -arylP(O)(OR5)2, a sugar, or a sugar phosphate
- or R1 and R2 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;
- R5 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 —(CH2)namino acid wherein the amino acid is connected to the compound through its alpha carbon atom, a —(CH2)npeptide 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):
- X1 is O, NH, or S;
- X2 is O, NH, or S;
- X3 is O, NH, or S;
- R1 and R2 each independently represents —H, —C(O)NH2, —S(O)NH2, —S(O)2NH2, —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, —(CH2)namino acid wherein the amino acid is connected through its alpha carbon atom, —(CH2)npeptide wherein the peptide is connected through the alpha carbon atom of one of its amino acids, —CH2OR5, —C(O)OR5, —C(O)NR5, —P(O)(OR5)2, —S(O)2NHR5, —SOR5, —S(O)2R5, -arylP(O)(OR5)2, a sugar, or a sugar phosphate
- or R1 and R2 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;
- R5 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, -1-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 —(CH2)namino acid wherein the amino acid is connected to the compound through its alpha carbon atom, a —(CH2)npeptide 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)
- X1 is O, NH, or S;
- X2 is O, NH, or S;
- X3 is O, NH, or S;
- R1 and R2 each independently represents, —H, —C(O)NH2, —S(O)NH2, —S(O)2NH2, —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, —(CH2)namino acid wherein the amino acid is connected through its alpha carbon atom, —(CH2)npeptide wherein the peptide is connected through the alpha carbon atom of one of its amino acids, —CH2OR5, —C(O)OR5, —C(O)NR5, —P(O)(OR5)2, —S(O)2NHR5, —SOR5, —S(O)2R5, -arylP(O)(OR5)2, a sugar, or a sugar phosphate,
- or R1 and R2 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;
- R5 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 —(CH2)namino acid wherein the amino acid is connected to the compound through its alpha carbon atom, a —(CH2)npeptide 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)
- X1 is O, NH, or S;
- X2 is O, NH, or S;
- X3 is O, NH, or S;
- R1 and R2 each independently represents, —H, —C(O)NH2, —S(O)NH2, —S(O)2NH2, —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, —(CH2)namino acid wherein the amino acid is connected through its alpha carbon atom, —(CH2)npeptide wherein the peptide is connected through the alpha carbon atom of one of its amino acids, —CH2OR5, —C(O)OR5, —C(O)NR5, —P(O)(OR5)2, —S(O)2NHR5, —SOR5, —S(O)2R5, -arylP(O)(OR5)2, a sugar, or a sugar phosphate,
- or R1 and R2 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;
- R5 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 —(CH2)namino acid wherein the amino acid is connected to the compound through its alpha carbon atom, a —(CH2)npeptide 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:
- and
- at least one active agent chosen from at least one natural product or natural product crude extract chosen from alfalfa, aloe, angelica, arnica, aristolochic acid, artemisia, astaxanthin, ashwaganda, astragalus, avens, beta-carotene, bilberry, birch, black cohosh, black horehound, blessed thistle, biotin, boldo, burdock, calcium, calendula, California poppy, caraway, cascara sagrada, catnip, cayenne, chaste tree fruit, chondroitin sulphate, copper, cramp bark, cranberry, dandelion, dang gui, devil's claw, echinacea, echinacea purpurea, echinacea pallida, eleuthero, evening primrose oil, european linden, european pennyroyal, fenugreek, feverfew, figwort, flax, folate, frankincense, garlic, gentian, ginger, ginkgo, globe artichoke, glucosamine, goldenseal, green tea, ground ivy, hawthorn, heal-all, hops, horse chestnut, horseradish, hyssop, illicium verum, juniper, licorice, linden, lungwort, lutein, melatonin, milk thistle, mugwort, niacin, pantothenic acid, peppermint, reishi mushroom, riboflavin, rosemary, saw palmetto, scullcap, selenium, schisandra, stinging nettle, St. John's wort, thuja, thyme, tomato, turmeric, valerian, willow bark, witch hazel, zeaxanthin, and mixtures thereof.
37 more elements
A composition comprising at least one compound chosen from compounds of formulae (I), (II), (III), and (IV):
- wherein
- in formula (I):
- X1 is O, NH, or S;
- X2 is O, NH, or S;
- X3 is O, NH, or S;
- R1 and R2 each independently represents —H, —C(O)NH2, —S(O)NH2, —S(O)2NH2, —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, —(CH2)namino acid wherein the amino acid is connected through its alpha carbon atom, —(CH2)npeptide wherein the peptide is connected through the alpha carbon atom of one of its amino acids, —CH2OR5, —C(O)OR5, —C(O)NR5, —P(O)(OR5)2, —S(O)2NHR5, —SOR5, —S(O)2R5, -arylP(O)(OR5)2, a sugar, or a sugar phosphate
- or R1 and R2 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;
- R5 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 —(CH2)namino acid wherein the amino acid is connected to the compound through its alpha carbon atom, a —(CH2)npeptide 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):
- X1 is O, NH, or S;
- X2 is O, NH, or S;
- X3 is O, NH, or S;
- R1 and R2 each independently represents —H, —C(O)NH2, —S(O)NH2, —S(O)2NH2, —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, —(CH2)namino acid wherein the amino acid is connected through its alpha carbon atom, —(CH2)npeptide wherein the peptide is connected through the alpha carbon atom of one of its amino acids, —CH2OR5, —C(O)OR5, —C(O)NR5, —P(O)(OR5)2, —S(O)2NHR5, —SOR5, —S(O)2R5, -arylP(O)(OR5)2, a sugar, or a sugar phosphate
- or R1 and R2 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;
- R5 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 —(CH2)namino acid wherein the amino acid is connected to the compound through its alpha carbon atom, a —(CH2)npeptide 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)
- X1 is O, NH, or S;
- X2 is O, NH, or S;
- X3 is O, NH, or S;
- R1 and R2 each independently represents, —H, —C(O)NH2, —S(O)NH2, —S(O)2NH2, —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, —(CH2)namino acid wherein the amino acid is connected through its alpha carbon atom, —(CH2)npeptide wherein the peptide is connected through the alpha carbon atom of one of its amino acids, —CH2OR5, —C(O)OR5, —C(O)NR5, —P(O)(OR5)2, —S(O)2NHR5, —SOR5, —S(O)2R5, -arylP(O)(OR5)2, a sugar, or a sugar phosphate,
- or R1 and R2 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;
- R5 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 —(CH2)namino acid wherein the amino acid is connected to the compound through its alpha carbon atom, a —(CH2)npeptide 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)
- X1 is O, NH, or S;
- X2 is O, NH, or S;
- X3 is O, NH, or S;
- R1 and R2 each independently represents, —H, —C(O)NH2, —S(O)NH2, —S(O)2NH2, —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, —(CH2)namino acid wherein the amino acid is connected through its alpha carbon atom, —(CH2)npeptide wherein the peptide is connected through the alpha carbon atom of one of its amino acids, —CH2OR5, —C(O)OR5, —C(O)NR5, —P(O)(OR5)2, —S(O)2NHR5, —SOR5, —S(O)2R5, -arylP(O)(OR5)2, a sugar, or a sugar phosphate,
- or R1 and R2 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;
- R5 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 —(CH2)namino acid wherein the amino acid is connected to the compound through its alpha carbon atom, a —(CH2)npeptide 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
- 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.
37 more elements
A method of using at least one compound of formula (I), (II), (III), or (IV):
- wherein
- in formula (I):
- X1 is O, NH, or S;
- X2 is O, NH, or S;
- X3 is O, NH, or S;
- R1 and R2 each independently represents —H, —C(O)NH2, —S(O)NH2, —S(O)2NH2, —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, —(CH2)namino acid wherein the amino acid is connected through its alpha carbon atom, —(CH2)npeptide wherein the peptide is connected through the alpha carbon atom of one of its amino acids, —CH2OR5, —C(O)OR5, —C(O)NR5, —P(O)(OR5)2, —S(O)2NHR5, —SOR5, —S(O)2R5, -arylP(O)(OR5)2, a sugar, or a sugar phosphate
- or R1 and R2 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;
- R5 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 —(CH2)namino acid wherein the amino acid is connected to the compound through its alpha carbon atom, a —(CH2)npeptide 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):
- X1 is O, NH, or S;
- X2 is O, NH, or S;
- X3 is O, NH, or S;
- R1 and R2 each independently represents —H, —C(O)NH2, —S(O)NH2, —S(O)2NH2, —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, —(CH2)namino acid wherein the amino acid is connected through its alpha carbon atom, —(CH2)npeptide wherein the peptide is connected through the alpha carbon atom of one of its amino acids, —CH2OR5, —C(O)OR5, —C(O)NR5, —P(O)(OR5)2, —S(O)2NHR5, —SOR5, —S(O)2R5, -arylP(O)(OR5)2, a sugar, or a sugar phosphate
- or R1 and R2 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;
- R5 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 —(CH2)namino acid wherein the amino acid is connected to the compound through its alpha carbon atom, a —(CH2)npeptide 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)
- X1 is O, NH, or S;
- X2 is O, NH, or S;
- X3 is O, NH, or S;
- R1 and R2 each independently represents, —H, —C(O)NH2, —S(O)NH2, —S(O)2NH2, —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, —(CH2)namino acid wherein the amino acid is connected through its alpha carbon atom, —(CH2)npeptide wherein the peptide is connected through the alpha carbon atom of one of its amino acids, —CH2OR5, —C(O)OR5, —C(O)NR5, —P(O)(OR5)2, —S(O)2NHR5, —SOR5, —S(O)2R5, -arylP(O)(OR5)2, a sugar, or a sugar phosphate,
- or R1 and R2 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;
- R5 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 —(CH2)namino acid wherein the amino acid is connected to the compound through its alpha carbon atom, a —(CH2)npeptide 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)
- X1 is O, NH, or S;
- X2 is O, NH, or S;
- X3 is O, NH, or S;
- R1 and R2 each independently represents, —H, —C(O)NH2, —S(O)NH2, —S(O)2NH2, —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, —(CH2)namino acid wherein the amino acid is connected through its alpha carbon atom, —(CH2)npeptide wherein the peptide is connected through the alpha carbon atom of one of its amino acids, —CH2OR5, —C(O)OR5, —C(O)NR5, —P(O)(OR5)2, —S(O)2NHR5, —SOR5, —S(O)2R5, -arylP(O)(OR5)2, a sugar, or a sugar phosphate,
- or R1 and R2 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;
- R5 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 —(CH2)namino acid wherein the amino acid is connected to the compound through its alpha carbon atom, a —(CH2)npeptide 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,
- said method comprising solubilizing at least one active agent in said at least one compound of formula (I), (II), (III), or (IV).
35 more elements
Dependencies are inferred from the claim text.