JP2020522514A5 - - Google Patents
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- JP2020522514A5 JP2020522514A5 JP2019566683A JP2019566683A JP2020522514A5 JP 2020522514 A5 JP2020522514 A5 JP 2020522514A5 JP 2019566683 A JP2019566683 A JP 2019566683A JP 2019566683 A JP2019566683 A JP 2019566683A JP 2020522514 A5 JP2020522514 A5 JP 2020522514A5
- Authority
- JP
- Japan
- Prior art keywords
- acyl
- acid
- independently
- agent
- amino acid
- Prior art date
- Legal status (The legal status 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 status listed.)
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- 125000002252 acyl group Chemical group 0.000 claims description 329
- 125000003158 alcohol group Chemical group 0.000 claims description 223
- 239000003795 chemical substances by application Substances 0.000 claims description 166
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 161
- 150000001413 amino acids Chemical class 0.000 claims description 126
- -1 indole-3-yl Chemical group 0.000 claims description 119
- 150000001412 amines Chemical group 0.000 claims description 106
- 239000002207 metabolite Substances 0.000 claims description 97
- 229940024606 amino acid Drugs 0.000 claims description 85
- 229940088594 vitamin Drugs 0.000 claims description 84
- 229930003231 vitamin Natural products 0.000 claims description 84
- 235000013343 vitamin Nutrition 0.000 claims description 84
- 239000011782 vitamin Substances 0.000 claims description 84
- 235000017807 phytochemicals Nutrition 0.000 claims description 77
- 229930000223 plant secondary metabolite Natural products 0.000 claims description 77
- 150000005846 sugar alcohols Chemical class 0.000 claims description 66
- 239000003613 bile acid Substances 0.000 claims description 57
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 claims description 57
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 56
- 229930195729 fatty acid Natural products 0.000 claims description 56
- 239000000194 fatty acid Substances 0.000 claims description 56
- 229940121375 antifungal agent Drugs 0.000 claims description 54
- 239000003429 antifungal agent Chemical class 0.000 claims description 53
- 229960004963 mesalazine Drugs 0.000 claims description 53
- 239000002253 acid Substances 0.000 claims description 51
- KBOPZPXVLCULAV-UHFFFAOYSA-N mesalamine Chemical compound NC1=CC=C(O)C(C(O)=O)=C1 KBOPZPXVLCULAV-UHFFFAOYSA-N 0.000 claims description 42
- 150000001720 carbohydrates Chemical class 0.000 claims description 39
- 235000014633 carbohydrates Nutrition 0.000 claims description 39
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 39
- 150000003722 vitamin derivatives Chemical class 0.000 claims description 39
- 238000001727 in vivo Methods 0.000 claims description 38
- 108010024636 Glutathione Proteins 0.000 claims description 36
- 229930003935 flavonoid Natural products 0.000 claims description 36
- 235000017173 flavonoids Nutrition 0.000 claims description 36
- 229960003180 glutathione Drugs 0.000 claims description 36
- 229920000768 polyamine Polymers 0.000 claims description 36
- 229940123208 Biguanide Drugs 0.000 claims description 34
- 150000002215 flavonoids Chemical class 0.000 claims description 34
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 claims description 33
- 230000002058 anti-hyperglycaemic effect Effects 0.000 claims description 33
- 229930013686 lignan Natural products 0.000 claims description 32
- 235000009408 lignans Nutrition 0.000 claims description 32
- 150000005692 lignans Chemical class 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 30
- 235000000346 sugar Nutrition 0.000 claims description 30
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 claims description 27
- 235000021466 carotenoid Nutrition 0.000 claims description 26
- 150000001747 carotenoids Chemical class 0.000 claims description 26
- 235000013824 polyphenols Nutrition 0.000 claims description 26
- 150000003436 stilbenoids Chemical class 0.000 claims description 24
- 235000005487 catechin Nutrition 0.000 claims description 23
- 229950001002 cianidanol Drugs 0.000 claims description 23
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 claims description 22
- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims description 20
- PDHAOJSHSJQANO-OWOJBTEDSA-N Oxyresveratrol Chemical class OC1=CC(O)=CC=C1\C=C\C1=CC(O)=CC(O)=C1 PDHAOJSHSJQANO-OWOJBTEDSA-N 0.000 claims description 20
- 108010017842 Telomerase Proteins 0.000 claims description 17
- 150000001414 amino alcohols Chemical class 0.000 claims description 17
- 239000012190 activator Substances 0.000 claims description 16
- 150000002576 ketones Chemical class 0.000 claims description 16
- 150000002966 pentacyclic triterpenoids Chemical class 0.000 claims description 16
- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 claims description 15
- HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 claims description 15
- HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 claims description 15
- 235000019152 folic acid Nutrition 0.000 claims description 15
- 239000011724 folic acid Substances 0.000 claims description 15
- OVBPIULPVIDEAO-UHFFFAOYSA-N N-Pteroyl-L-glutaminsaeure Natural products C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-UHFFFAOYSA-N 0.000 claims description 14
- 229960000304 folic acid Drugs 0.000 claims description 14
- HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 claims description 13
- PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 claims description 13
- 150000007513 acids Chemical class 0.000 claims description 13
- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 claims description 13
- 229940074410 trehalose Drugs 0.000 claims description 13
- RZZPDXZPRHQOCG-OJAKKHQRSA-M CDP-choline(1-) Chemical class O[C@@H]1[C@H](O)[C@@H](COP([O-])(=O)OP([O-])(=O)OCC[N+](C)(C)C)O[C@H]1N1C(=O)N=C(N)C=C1 RZZPDXZPRHQOCG-OJAKKHQRSA-M 0.000 claims description 11
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 11
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
- 229960001284 citicoline Drugs 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 11
- 150000007523 nucleic acids Chemical class 0.000 claims description 11
- 102000039446 nucleic acids Human genes 0.000 claims description 11
- 108020004707 nucleic acids Proteins 0.000 claims description 11
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 11
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 claims description 10
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 10
- 206010012601 diabetes mellitus Diseases 0.000 claims description 10
- 229960000815 ezetimibe Drugs 0.000 claims description 10
- OLNTVTPDXPETLC-XPWALMASSA-N ezetimibe Chemical class N1([C@@H]([C@H](C1=O)CC[C@H](O)C=1C=CC(F)=CC=1)C=1C=CC(O)=CC=1)C1=CC=C(F)C=C1 OLNTVTPDXPETLC-XPWALMASSA-N 0.000 claims description 10
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 claims description 9
- IHVRWFJGOIWMGC-NSCUHMNNSA-N 4-methoxyresveratrol Chemical class C1=CC(OC)=CC=C1\C=C\C1=CC(O)=CC(O)=C1 IHVRWFJGOIWMGC-NSCUHMNNSA-N 0.000 claims description 9
- 229930153442 Curcuminoid Natural products 0.000 claims description 9
- SEOVTRFCIGRIMH-UHFFFAOYSA-N Indole-3-acetic acid Natural products C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 claims description 9
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 claims description 9
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims description 9
- IHVRWFJGOIWMGC-UHFFFAOYSA-N desoxyrhapontigenin Chemical class C1=CC(OC)=CC=C1C=CC1=CC(O)=CC(O)=C1 IHVRWFJGOIWMGC-UHFFFAOYSA-N 0.000 claims description 9
- IIXHQGSINFQLRR-UHFFFAOYSA-N Piceatannol Natural products Oc1ccc(C=Cc2c(O)c(O)c3CCCCc3c2O)cc1O IIXHQGSINFQLRR-UHFFFAOYSA-N 0.000 claims description 8
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims description 8
- CDRPUGZCRXZLFL-OWOJBTEDSA-N piceatannol Chemical class OC1=CC(O)=CC(\C=C\C=2C=C(O)C(O)=CC=2)=C1 CDRPUGZCRXZLFL-OWOJBTEDSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 150000001298 alcohols Chemical class 0.000 claims description 7
- 208000015181 infectious disease Diseases 0.000 claims description 7
- 125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 claims description 6
- 230000000975 bioactive effect Effects 0.000 claims description 6
- 239000003617 indole-3-acetic acid Substances 0.000 claims description 6
- 230000001737 promoting effect Effects 0.000 claims description 6
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 206010061218 Inflammation Diseases 0.000 claims description 5
- 208000008589 Obesity Diseases 0.000 claims description 5
- 125000001589 carboacyl group Chemical group 0.000 claims description 5
- 125000003312 cerotoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000003074 decanoyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 claims description 5
- 230000004054 inflammatory process Effects 0.000 claims description 5
- 235000020824 obesity Nutrition 0.000 claims description 5
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 claims description 5
- VLEUZFDZJKSGMX-ONEGZZNKSA-N pterostilbene Chemical compound COC1=CC(OC)=CC(\C=C\C=2C=CC(O)=CC=2)=C1 VLEUZFDZJKSGMX-ONEGZZNKSA-N 0.000 claims description 5
- 230000001105 regulatory effect Effects 0.000 claims description 5
- 208000024891 symptom Diseases 0.000 claims description 5
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 claims description 4
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 4
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 4
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 claims description 4
- 235000020661 alpha-linolenic acid Nutrition 0.000 claims description 4
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
- 229930182830 galactose Natural products 0.000 claims description 4
- 125000004383 glucosinolate group Chemical group 0.000 claims description 4
- 229920002674 hyaluronan Polymers 0.000 claims description 4
- 229960003160 hyaluronic acid Drugs 0.000 claims description 4
- JCQLYHFGKNRPGE-FCVZTGTOSA-N lactulose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 JCQLYHFGKNRPGE-FCVZTGTOSA-N 0.000 claims description 4
- 229960000511 lactulose Drugs 0.000 claims description 4
- PFCRQPBOOFTZGQ-UHFFFAOYSA-N lactulose keto form Natural products OCC(=O)C(O)C(C(O)CO)OC1OC(CO)C(O)C(O)C1O PFCRQPBOOFTZGQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000403 lignoceroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 229960004488 linolenic acid Drugs 0.000 claims description 4
- 230000000813 microbial effect Effects 0.000 claims description 4
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- DTOSIQBPPRVQHS-PDBXOOCHSA-N (Z,Z,Z)-Octadeca-9,12,15-trienoic acid Natural products CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 claims description 3
- 206010022489 Insulin Resistance Diseases 0.000 claims description 3
- 125000001124 arachidoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000003910 behenoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 229960001231 choline Drugs 0.000 claims description 3
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 claims description 3
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- SEBPBUWRSRLFQT-UHFFFAOYSA-N hydroperoxy(trihydroxy)silane Chemical class OO[Si](O)(O)O SEBPBUWRSRLFQT-UHFFFAOYSA-N 0.000 claims description 3
- 125000000400 lauroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 210000003205 muscle Anatomy 0.000 claims description 3
- 230000037257 muscle growth Effects 0.000 claims description 3
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000001402 nonanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 230000036559 skin health Effects 0.000 claims description 3
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 230000000699 topical effect Effects 0.000 claims description 3
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 3
- YUFFSWGQGVEMMI-JLNKQSITSA-N (7Z,10Z,13Z,16Z,19Z)-docosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O YUFFSWGQGVEMMI-JLNKQSITSA-N 0.000 claims description 2
- HOBAELRKJCKHQD-UHFFFAOYSA-N (8Z,11Z,14Z)-8,11,14-eicosatrienoic acid Natural products CCCCCC=CCC=CCC=CCCCCCCC(O)=O HOBAELRKJCKHQD-UHFFFAOYSA-N 0.000 claims description 2
- 235000021298 Dihomo-γ-linolenic acid Nutrition 0.000 claims description 2
- 108090000790 Enzymes Proteins 0.000 claims description 2
- 102000004190 Enzymes Human genes 0.000 claims description 2
- 229930091371 Fructose Natural products 0.000 claims description 2
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims description 2
- 239000005715 Fructose Substances 0.000 claims description 2
- 229920001202 Inulin Polymers 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
- 229960005135 eicosapentaenoic acid Drugs 0.000 claims description 2
- 235000020673 eicosapentaenoic acid Nutrition 0.000 claims description 2
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| WO2020037009A1 (en) | 2018-08-13 | 2020-02-20 | Flagship Pioneering Innovations V, Inc. | Conjugates and methods of using the same |
| ES3069209T3 (en) | 2018-11-07 | 2026-06-04 | Univ Minnesota | Analgesic and anti-addictive compositions for treatment of chronic pain and opioid addiction |
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| CN113993833B (zh) * | 2019-06-12 | 2024-05-10 | 凯托利皮克斯治疗有限责任公司 | 酰基封端的3-羟基羧酸及其盐和酯的生产方法 |
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| US10738077B1 (en) * | 2020-04-09 | 2020-08-11 | Shaanxi University Of Science And Technology | Hydroxytyrosol ursodeoxycholic acid ester with antioxidant activity and a method of preparing the same |
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| WO2022140580A1 (en) * | 2020-12-24 | 2022-06-30 | Orn Almarsson | Xanthophyll derivatives |
| CN112979464B (zh) * | 2020-12-28 | 2022-02-11 | 中国农业科学院农产品加工研究所 | 白藜芦醇共轭亚油酸酯及其制备方法 |
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| CN113045416B (zh) * | 2021-03-23 | 2023-08-18 | 南京纽邦生物科技有限公司 | 一种(r)-3-羟基丁酰-(r)-3-羟基丁酯的制备方法 |
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| WO2023084531A1 (en) * | 2021-11-12 | 2023-05-19 | Celagenex Research (India) Pvt. Ltd. | A synergistic composition for activating intracellular secondary messenger(camp) pathway |
| CN114957004A (zh) * | 2022-05-20 | 2022-08-30 | 上海远志昌浦生物科技有限公司 | 一种(r)-3-羟基丁酸-(r)-羟基丁酯及其中间体的合成方法和应用 |
| CN115417865A (zh) * | 2022-09-20 | 2022-12-02 | 上海予君生物科技发展有限公司 | 一种依拉地平中间体的制备工艺 |
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| EP4692049A1 (en) * | 2023-03-30 | 2026-02-11 | Mitsui Chemicals, Inc. | Amide compound |
| WO2025038998A1 (en) * | 2023-08-17 | 2025-02-20 | University Of Wyoming | Materials and methods for inhibiting, preventing, and dispersing biofilms |
| FR3153997A1 (fr) * | 2023-10-13 | 2025-04-18 | L'oreal | Utilisation cosmétique d'au moins l’urolithine B sur une peau sensible |
| EP4791374A1 (en) * | 2023-10-13 | 2026-08-19 | L'oreal | Cosmetic use of at least urolithin b or c on a sensitive skin |
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| US5385938B1 (en) * | 1986-12-23 | 1997-07-15 | Tristrata Inc | Method of using glycolic acid for treating wrinkles |
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| DE102005046237A1 (de) * | 2005-09-28 | 2007-04-05 | Südzucker Aktiengesellschaft Mannheim/Ochsenfurt | Buttersäureester von Kohlenhydraten und Kohlenhydratpolyolen |
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| JP2016222612A (ja) * | 2015-06-01 | 2016-12-28 | 昭和電工株式会社 | 化粧料または皮膚外用剤 |
| CA3003283A1 (en) * | 2015-11-24 | 2017-06-01 | Theravance Biopharma R&D Ip, Llc | Prodrugs of a jak inhibitor compound for treatment of gastrointestinal inflammatory disease |
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2018
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- 2018-06-05 MX MX2019014539A patent/MX2019014539A/es unknown
- 2018-06-05 WO PCT/US2018/036113 patent/WO2018226732A1/en not_active Ceased
- 2018-06-05 JP JP2019566683A patent/JP2020522514A/ja active Pending
- 2018-06-05 RU RU2019144960A patent/RU2019144960A/ru not_active Application Discontinuation
- 2018-06-05 BR BR112019025614-8A patent/BR112019025614A2/pt not_active Application Discontinuation
- 2018-06-05 KR KR1020197038304A patent/KR20200011972A/ko not_active Withdrawn
- 2018-06-05 SG SG11201910198U patent/SG11201910198UA/en unknown
- 2018-06-05 EP EP18814051.1A patent/EP3634430B1/en active Active
- 2018-06-05 CA CA3062067A patent/CA3062067A1/en active Pending
- 2018-06-05 AU AU2018281327A patent/AU2018281327A1/en not_active Abandoned
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2019
- 2019-11-28 IL IL271025A patent/IL271025A/en unknown
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2023
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