KR102399290B1 - 10-하이드록시-2-데센산을 포함하는 방법 및 조성물 - Google Patents
10-하이드록시-2-데센산을 포함하는 방법 및 조성물 Download PDFInfo
- Publication number
- KR102399290B1 KR102399290B1 KR1020167034149A KR20167034149A KR102399290B1 KR 102399290 B1 KR102399290 B1 KR 102399290B1 KR 1020167034149 A KR1020167034149 A KR 1020167034149A KR 20167034149 A KR20167034149 A KR 20167034149A KR 102399290 B1 KR102399290 B1 KR 102399290B1
- Authority
- KR
- South Korea
- Prior art keywords
- day
- amount
- acid
- hydroxy
- pufa
- 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.)
- Active
Links
- KUPHXIFBKAORGY-UHFFFAOYSA-N 2-amino-3-iodo-4-methylbenzoic acid Chemical compound CC1=CC=C(C(O)=O)C(N)=C1I KUPHXIFBKAORGY-UHFFFAOYSA-N 0.000 title claims abstract description 88
- QHBZHVUGQROELI-UHFFFAOYSA-N Royal Jelly acid Natural products OCCCCCCCC=CC(O)=O QHBZHVUGQROELI-UHFFFAOYSA-N 0.000 title claims abstract description 88
- 239000000203 mixture Substances 0.000 title claims abstract description 52
- 238000000034 method Methods 0.000 title claims description 28
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 claims abstract description 114
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 29
- MBMBGCFOFBJSGT-KUBAVDMBSA-N all-cis-docosa-4,7,10,13,16,19-hexaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 claims description 79
- 235000020669 docosahexaenoic acid Nutrition 0.000 claims description 54
- 229940090949 docosahexaenoic acid Drugs 0.000 claims description 36
- 230000004580 weight loss Effects 0.000 claims description 25
- 235000020660 omega-3 fatty acid Nutrition 0.000 claims description 14
- 229940012843 omega-3 fatty acid Drugs 0.000 claims description 12
- DVSZKTAMJJTWFG-SKCDLICFSA-N (2e,4e,6e,8e,10e,12e)-docosa-2,4,6,8,10,12-hexaenoic acid Chemical compound CCCCCCCCC\C=C\C=C\C=C\C=C\C=C\C=C\C(O)=O DVSZKTAMJJTWFG-SKCDLICFSA-N 0.000 claims description 11
- GZJLLYHBALOKEX-UHFFFAOYSA-N 6-Ketone, O18-Me-Ussuriedine Natural products CC=CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O GZJLLYHBALOKEX-UHFFFAOYSA-N 0.000 claims description 11
- CYQFCXCEBYINGO-IAGOWNOFSA-N delta1-THC Chemical compound C1=C(C)CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3[C@@H]21 CYQFCXCEBYINGO-IAGOWNOFSA-N 0.000 claims description 11
- KAUVQQXNCKESLC-UHFFFAOYSA-N docosahexaenoic acid (DHA) Natural products COC(=O)C(C)NOCC1=CC=CC=C1 KAUVQQXNCKESLC-UHFFFAOYSA-N 0.000 claims description 11
- 201000010099 disease Diseases 0.000 claims description 7
- 235000021588 free fatty acids Nutrition 0.000 claims description 7
- 239000002775 capsule Substances 0.000 claims description 6
- 125000004494 ethyl ester group Chemical class 0.000 claims description 6
- -1 glyceride ester Chemical class 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 230000005764 inhibitory process Effects 0.000 claims 2
- 230000037221 weight management Effects 0.000 abstract description 35
- 208000019901 Anxiety disease Diseases 0.000 abstract description 23
- 230000004968 inflammatory condition Effects 0.000 abstract description 23
- 230000035935 pregnancy Effects 0.000 abstract description 22
- 230000036506 anxiety Effects 0.000 abstract description 21
- 230000003930 cognitive ability Effects 0.000 abstract description 21
- 241000700159 Rattus Species 0.000 description 29
- 208000035475 disorder Diseases 0.000 description 21
- 241000699670 Mus sp. Species 0.000 description 15
- 241001465754 Metazoa Species 0.000 description 14
- 210000004027 cell Anatomy 0.000 description 12
- 235000014113 dietary fatty acids Nutrition 0.000 description 11
- 229930195729 fatty acid Natural products 0.000 description 11
- 239000000194 fatty acid Substances 0.000 description 11
- 244000005700 microbiome Species 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 230000032683 aging Effects 0.000 description 9
- 150000004665 fatty acids Chemical class 0.000 description 9
- 229940109850 royal jelly Drugs 0.000 description 9
- 230000035882 stress Effects 0.000 description 9
- QHBZHVUGQROELI-SOFGYWHQSA-N (E)-10-hydroxydec-2-enoic acid Chemical compound OCCCCCCC\C=C\C(O)=O QHBZHVUGQROELI-SOFGYWHQSA-N 0.000 description 8
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 8
- 230000037396 body weight Effects 0.000 description 8
- 230000008901 benefit Effects 0.000 description 7
- 230000002829 reductive effect Effects 0.000 description 7
- 210000002569 neuron Anatomy 0.000 description 6
- 150000003904 phospholipids Chemical class 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 230000030833 cell death Effects 0.000 description 5
- 230000036541 health Effects 0.000 description 5
- 238000000338 in vitro Methods 0.000 description 5
- 239000003550 marker Substances 0.000 description 5
- 235000002639 sodium chloride Nutrition 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 5
- 241000233866 Fungi Species 0.000 description 4
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 4
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 4
- 235000021342 arachidonic acid Nutrition 0.000 description 4
- 229940114079 arachidonic acid Drugs 0.000 description 4
- 230000036995 brain health Effects 0.000 description 4
- 230000001149 cognitive effect Effects 0.000 description 4
- 150000001982 diacylglycerols Chemical class 0.000 description 4
- 235000005911 diet Nutrition 0.000 description 4
- 230000037213 diet Effects 0.000 description 4
- 150000002148 esters Chemical group 0.000 description 4
- 230000013016 learning Effects 0.000 description 4
- 235000020978 long-chain polyunsaturated fatty acids Nutrition 0.000 description 4
- 150000002759 monoacylglycerols Chemical class 0.000 description 4
- 230000000624 ovulatory effect Effects 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 206010021143 Hypoxia Diseases 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- 230000002159 abnormal effect Effects 0.000 description 3
- 238000000540 analysis of variance Methods 0.000 description 3
- 210000004556 brain Anatomy 0.000 description 3
- 201000011510 cancer Diseases 0.000 description 3
- 206010009887 colitis Diseases 0.000 description 3
- 235000020940 control diet Nutrition 0.000 description 3
- 231100000673 dose–response relationship Toxicity 0.000 description 3
- 210000001320 hippocampus Anatomy 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 230000000813 microbial effect Effects 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 3
- 239000013641 positive control Substances 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 238000010186 staining Methods 0.000 description 3
- 239000003826 tablet Substances 0.000 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 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 description 2
- FWBHETKCLVMNFS-UHFFFAOYSA-N 4',6-Diamino-2-phenylindol Chemical compound C1=CC(C(=N)N)=CC=C1C1=CC2=CC=C(C(N)=N)C=C2N1 FWBHETKCLVMNFS-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 235000021298 Dihomo-γ-linolenic acid Nutrition 0.000 description 2
- 235000021294 Docosapentaenoic acid Nutrition 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- OPGOLNDOMSBSCW-CLNHMMGSSA-N Fursultiamine hydrochloride Chemical compound Cl.C1CCOC1CSSC(\CCO)=C(/C)N(C=O)CC1=CN=C(C)N=C1N OPGOLNDOMSBSCW-CLNHMMGSSA-N 0.000 description 2
- 208000018522 Gastrointestinal disease Diseases 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
- 241000235575 Mortierella Species 0.000 description 2
- 208000002500 Primary Ovarian Insufficiency Diseases 0.000 description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
- 241001467333 Thraustochytriaceae Species 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- JAZBEHYOTPTENJ-JLNKQSITSA-N all-cis-5,8,11,14,17-icosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JAZBEHYOTPTENJ-JLNKQSITSA-N 0.000 description 2
- 230000006399 behavior Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000012258 culturing Methods 0.000 description 2
- 208000010643 digestive system disease Diseases 0.000 description 2
- HOBAELRKJCKHQD-QNEBEIHSSA-N dihomo-γ-linolenic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(O)=O HOBAELRKJCKHQD-QNEBEIHSSA-N 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000020673 eicosapentaenoic acid Nutrition 0.000 description 2
- 229960005135 eicosapentaenoic acid Drugs 0.000 description 2
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 description 2
- 239000002158 endotoxin Substances 0.000 description 2
- 238000013290 female long evans rat Methods 0.000 description 2
- 230000004720 fertilization Effects 0.000 description 2
- 208000018685 gastrointestinal system disease Diseases 0.000 description 2
- 229930195712 glutamate Natural products 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 230000007954 hypoxia Effects 0.000 description 2
- 210000002865 immune cell Anatomy 0.000 description 2
- 208000000509 infertility Diseases 0.000 description 2
- 230000036512 infertility Effects 0.000 description 2
- 231100000535 infertility Toxicity 0.000 description 2
- 229920006008 lipopolysaccharide Polymers 0.000 description 2
- 150000004668 long chain fatty acids Chemical class 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 230000015654 memory Effects 0.000 description 2
- 230000002438 mitochondrial effect Effects 0.000 description 2
- 230000036651 mood Effects 0.000 description 2
- 230000027758 ovulation cycle Effects 0.000 description 2
- 201000010065 polycystic ovary syndrome Diseases 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 208000016685 primary ovarian failure Diseases 0.000 description 2
- 241000894007 species Species 0.000 description 2
- JIWBIWFOSCKQMA-UHFFFAOYSA-N stearidonic acid Natural products CCC=CCC=CCC=CCC=CCCCCC(O)=O JIWBIWFOSCKQMA-UHFFFAOYSA-N 0.000 description 2
- 230000000638 stimulation Effects 0.000 description 2
- 230000009469 supplementation Effects 0.000 description 2
- MJYQFWSXKFLTAY-OVEQLNGDSA-N (2r,3r)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diol;(2r,3r,4s,5s,6r)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O.C1=C(O)C(OC)=CC(C[C@@H](CO)[C@H](CO)CC=2C=C(OC)C(O)=CC=2)=C1 MJYQFWSXKFLTAY-OVEQLNGDSA-N 0.000 description 1
- LOGFVTREOLYCPF-KXNHARMFSA-N (2s,3r)-2-[[(2r)-1-[(2s)-2,6-diaminohexanoyl]pyrrolidine-2-carbonyl]amino]-3-hydroxybutanoic acid Chemical compound C[C@@H](O)[C@@H](C(O)=O)NC(=O)[C@H]1CCCN1C(=O)[C@@H](N)CCCCN LOGFVTREOLYCPF-KXNHARMFSA-N 0.000 description 1
- MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 241001474374 Blennius Species 0.000 description 1
- 240000004355 Borago officinalis Species 0.000 description 1
- 235000007689 Borago officinalis Nutrition 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000283153 Cetacea Species 0.000 description 1
- 241000238424 Crustacea Species 0.000 description 1
- 241000199913 Crypthecodinium Species 0.000 description 1
- 102000004127 Cytokines Human genes 0.000 description 1
- 108090000695 Cytokines Proteins 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 101000914514 Homo sapiens T-cell-specific surface glycoprotein CD28 Proteins 0.000 description 1
- 241000257303 Hymenoptera Species 0.000 description 1
- 102000003777 Interleukin-1 beta Human genes 0.000 description 1
- 108090000193 Interleukin-1 beta Proteins 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 102000009664 Microtubule-Associated Proteins Human genes 0.000 description 1
- 108010020004 Microtubule-Associated Proteins Proteins 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000219925 Oenothera Species 0.000 description 1
- 235000004496 Oenothera biennis Nutrition 0.000 description 1
- 102100027213 T-cell-specific surface glycoprotein CD28 Human genes 0.000 description 1
- 241000233675 Thraustochytrium Species 0.000 description 1
- 102000005789 Vascular Endothelial Growth Factors Human genes 0.000 description 1
- 108010019530 Vascular Endothelial Growth Factors Proteins 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 230000033115 angiogenesis Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000004958 brain cell Anatomy 0.000 description 1
- BQRGNLJZBFXNCZ-UHFFFAOYSA-N calcein am Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC(CN(CC(=O)OCOC(C)=O)CC(=O)OCOC(C)=O)=C(OC(C)=O)C=C1OC1=C2C=C(CN(CC(=O)OCOC(C)=O)CC(=O)OCOC(=O)C)C(OC(C)=O)=C1 BQRGNLJZBFXNCZ-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 210000003855 cell nucleus Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 210000002889 endothelial cell Anatomy 0.000 description 1
- 230000001973 epigenetic effect Effects 0.000 description 1
- GTSMOYLSFUBTMV-UHFFFAOYSA-N ethidium homodimer Chemical compound [H+].[H+].[Cl-].[Cl-].[Cl-].[Cl-].C12=CC(N)=CC=C2C2=CC=C(N)C=C2C(C)=[N+]1CCCNCCNCCC[N+](C1=CC(N)=CC=C1C1=CC=C(N)C=C11)=C1C1=CC=CC=C1 GTSMOYLSFUBTMV-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 230000035558 fertility Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000004426 flaxseed Nutrition 0.000 description 1
- 238000002073 fluorescence micrograph Methods 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000012631 food intake Nutrition 0.000 description 1
- 235000020664 gamma-linolenic acid Nutrition 0.000 description 1
- 230000002518 glial effect Effects 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- 125000005908 glyceryl ester group Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229940121372 histone deacetylase inhibitor Drugs 0.000 description 1
- 239000003276 histone deacetylase inhibitor Substances 0.000 description 1
- 230000001146 hypoxic effect Effects 0.000 description 1
- 230000005918 in vitro anti-tumor Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 230000000366 juvenile effect Effects 0.000 description 1
- 230000001418 larval effect Effects 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000008297 liquid dosage form Substances 0.000 description 1
- 235000020667 long-chain omega-3 fatty acid Nutrition 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 210000002540 macrophage Anatomy 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000013011 mating Effects 0.000 description 1
- 150000004667 medium chain fatty acids Chemical class 0.000 description 1
- 210000002241 neurite Anatomy 0.000 description 1
- 230000000626 neurodegenerative effect Effects 0.000 description 1
- 230000001123 neurodevelopmental effect Effects 0.000 description 1
- 230000004766 neurogenesis Effects 0.000 description 1
- 239000006014 omega-3 oil Substances 0.000 description 1
- 235000020665 omega-6 fatty acid Nutrition 0.000 description 1
- 229940033080 omega-6 fatty acid Drugs 0.000 description 1
- 238000012346 open field test Methods 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- XJMOSONTPMZWPB-UHFFFAOYSA-M propidium iodide Chemical compound [I-].[I-].C12=CC(N)=CC=C2C2=CC=C(N)C=C2[N+](CCC[N+](C)(CC)CC)=C1C1=CC=CC=C1 XJMOSONTPMZWPB-UHFFFAOYSA-M 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004666 short chain fatty acids Chemical class 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000006886 spatial memory Effects 0.000 description 1
- 150000003408 sphingolipids Chemical class 0.000 description 1
- 210000000130 stem cell Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000012549 training Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 210000003606 umbilical vein Anatomy 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 230000031836 visual learning Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
- A61K31/201—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids having one or two double bonds, e.g. oleic, linoleic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
- A61K31/202—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids having three or more double bonds, e.g. linolenic
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
Landscapes
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Reproductive Health (AREA)
- Psychiatry (AREA)
- Endocrinology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Gynecology & Obstetrics (AREA)
- Child & Adolescent Psychology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pregnancy & Childbirth (AREA)
- Hospice & Palliative Care (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201461990283P | 2014-05-08 | 2014-05-08 | |
| US61/990,283 | 2014-05-08 | ||
| PCT/US2015/029790 WO2015171960A1 (en) | 2014-05-08 | 2015-05-07 | Methods and compositions comprising 10-hydroxy-2-decenoic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20170003637A KR20170003637A (ko) | 2017-01-09 |
| KR102399290B1 true KR102399290B1 (ko) | 2022-05-17 |
Family
ID=54393026
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020167034149A Active KR102399290B1 (ko) | 2014-05-08 | 2015-05-07 | 10-하이드록시-2-데센산을 포함하는 방법 및 조성물 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US10004711B2 (enExample) |
| EP (1) | EP3139741A4 (enExample) |
| JP (1) | JP6819957B2 (enExample) |
| KR (1) | KR102399290B1 (enExample) |
| CN (1) | CN106470547B (enExample) |
| BR (1) | BR112016026143A2 (enExample) |
| TW (1) | TWI743022B (enExample) |
| WO (1) | WO2015171960A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11197840B2 (en) * | 2015-12-04 | 2021-12-14 | Wah Chin BOON | Methods of treating or alleviating mental disorders and associated symptoms |
| WO2019195658A1 (en) | 2018-04-05 | 2019-10-10 | Dana-Farber Cancer Institute, Inc. | Sting levels as a biomarker for cancer immunotherapy |
| CN108310026A (zh) * | 2018-04-28 | 2018-07-24 | 宁夏医科大学 | 月见草油在改善多囊卵巢综合征慢性炎症方面的应用 |
| JP7240714B2 (ja) * | 2019-01-24 | 2023-03-16 | 株式会社山田養蜂場本社 | γヒドロキシ酪酸受容体結合剤 |
| CN110916088A (zh) * | 2019-11-04 | 2020-03-27 | 齐鲁工业大学 | 一种适合炎性肠病人群的全营养特医食品及制备方法 |
| CN112094790B (zh) * | 2020-11-17 | 2021-03-02 | 河北一然生物科技有限公司 | 一种调节肠道菌群的植物乳杆菌lp45活菌制剂及应用 |
| TWI793922B (zh) * | 2021-12-14 | 2023-02-21 | 彥臣生技藥品股份有限公司 | 一種用於提升認知能力之組合物及其用途 |
| CN116570582A (zh) * | 2023-05-19 | 2023-08-11 | 中国药科大学 | 10-羟基癸烯酸在制备重度抑郁治疗药物中的应用 |
| CN119745857A (zh) * | 2024-12-02 | 2025-04-04 | 温州医科大学 | 10-羟基-2-癸烯酸在药物制备中的应用 |
Family Cites Families (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1033843A (en) | 1964-05-26 | 1966-06-22 | Eustace Cecil Barton Wright | Pharmaceutical composition for treating thermatoid arthritis |
| GB1145623A (en) | 1966-03-09 | 1969-03-19 | Eustace Cecil Barton Wright | Pharmaceutical composition |
| JPH10114652A (ja) | 1996-10-15 | 1998-05-06 | Dokutaazu Kosumeteikusu:Kk | 津液改善剤及びそれを含有する経口投与用組成物 |
| AU7222598A (en) * | 1997-04-29 | 1998-11-24 | Scotia Holdings Plc | Treatment of depression and anxiety using docosahexaenoic acid or natural antioxidants |
| FR2773484B1 (fr) * | 1998-01-09 | 2001-03-30 | Pierre Moreau | Nouvelles compositions a effet synergique entre micronutriments et substances d'origine vivante |
| DE19844022C1 (de) | 1998-09-25 | 2000-05-25 | Sherif Sabry Ragab Mekkawi | Verwendung von eisenbindenden Glycoproteinen und/oder 10-Hydroxy-2-decensäure in Verbindung mit Thymochinon zur Behandlung von AIDS |
| WO2001091575A1 (en) * | 2000-06-01 | 2001-12-06 | United Feeds, Inc. | Animal food and method |
| FR2825919B1 (fr) * | 2001-06-14 | 2004-06-11 | Oreal | Utilisation d'au moins un derive de l'acide 10-hydroxy-2- decenoique dans des compositions destinees a traiter les signes cutanes du vieillissement |
| FR2829491B1 (fr) | 2001-09-12 | 2005-09-30 | Diverchim | Procede de preparation des hydroxy-acides gras insatures et de leurs esters, leur utilisation comme agent anti-collagenase |
| JP2005519939A (ja) * | 2002-03-08 | 2005-07-07 | モンサント テクノロジー エルエルシー | 炎症性疾患の治療および予防 |
| KR20050057127A (ko) | 2002-09-06 | 2005-06-16 | 하야시바라 겐 | 정제 로얄 젤리 |
| JP2004131407A (ja) * | 2002-10-09 | 2004-04-30 | Yamada Bee Farm | ローヤルゼリー又はその水溶性画分を有効成分とする抗うつ性組成物 |
| JP4657778B2 (ja) | 2004-03-30 | 2011-03-23 | 曽田香料株式会社 | アラキドン酸代謝抑制剤 |
| JP4727939B2 (ja) | 2004-03-31 | 2011-07-20 | アピ株式会社 | 低アレルゲン化ローヤルゼリーの製造方法 |
| JP4579620B2 (ja) * | 2004-08-25 | 2010-11-10 | アピ株式会社 | エストロゲン様作用剤及びその製造方法、並びに骨粗しょう症予防剤及び骨粗しょう症治療剤 |
| CN1836671A (zh) | 2005-03-21 | 2006-09-27 | 通化盛和药业股份有限公司 | 一种中药软胶囊及其制备方法和质量控制方法 |
| FR2892410B1 (fr) | 2005-10-21 | 2010-10-15 | Fabre Pierre Dermo Cosmetique | Nouveaux hydro-acides gras insatures et leur utilisation dermo cosmetologique |
| CA2632934A1 (en) * | 2005-12-20 | 2007-07-05 | Novozymes Biologicals, Inc. | Surfactants systems for surface cleaning |
| CN101370490A (zh) * | 2005-12-29 | 2009-02-18 | 希尔氏宠物营养品公司 | 用于预防或治疗炎症性肠病的组合物及其制备方法 |
| WO2007130581A2 (en) | 2006-05-04 | 2007-11-15 | Hardwicke Susan B | Compositions and methods for psychiatric conditions and cognition enhancement |
| JP4749366B2 (ja) | 2007-03-23 | 2011-08-17 | 株式会社山田養蜂場本社 | ローヤルゼリー粉末からなる錠剤およびその製造方法 |
| JPWO2009014105A1 (ja) | 2007-07-20 | 2010-10-07 | 株式会社山田養蜂場本社 | 新規カルボン酸およびそれを有効成分とする抗うつ用組成物 |
| JP2009274961A (ja) | 2008-05-12 | 2009-11-26 | Api Co Ltd | 吸収促進剤 |
| WO2009154197A1 (ja) * | 2008-06-17 | 2009-12-23 | ジャパンローヤルゼリー株式会社 | 認知障害改善剤 |
| JP2010111646A (ja) * | 2008-11-07 | 2010-05-20 | Hayashibara Biochem Lab Inc | 潰瘍性大腸炎治療剤 |
| JP2010260833A (ja) * | 2009-05-11 | 2010-11-18 | Daicho Kikaku:Kk | 抗自己免疫疾患剤 |
| CN101570482B (zh) | 2009-06-09 | 2012-12-26 | 李应阳 | 由ω-氯辛醇合成蜂王酸的方法 |
| JP2012031153A (ja) * | 2010-06-29 | 2012-02-16 | Takara Bio Inc | 脂肪燃焼促進剤 |
| JP5770453B2 (ja) | 2010-11-22 | 2015-08-26 | 八幡物産株式会社 | ローヤルゼリー含有組成物及びソフトカプセル |
| JP5923699B2 (ja) * | 2011-03-30 | 2016-05-25 | アピ株式会社 | 老化防止剤 |
| EP2726086A4 (en) * | 2011-06-30 | 2015-04-29 | Nitromega Corp | COMPOSITIONS WITH NITRO FATTY ACIDS |
| CN102408395B (zh) | 2011-10-24 | 2014-04-02 | 广西师范大学 | 新的哌嗪和高哌嗪类衍生物及其制备方法和应用 |
| WO2013066152A1 (en) * | 2011-10-31 | 2013-05-10 | N.V. Nutricia | Method for improving executive function |
| EP2822403B1 (en) * | 2012-03-07 | 2022-05-04 | Children's Medical Center Corporation | Methods and uses for enhancing, improving, or increasing fertility or reproductive function |
| CN104427887A (zh) * | 2012-03-14 | 2015-03-18 | 雅培制药有限公司 | 包含RRR-α生育酚和多不饱和脂肪酸的营养组合物 |
| US20140271844A1 (en) * | 2013-03-15 | 2014-09-18 | Nitromega Corp. | Compositions containing nitro fatty acids |
-
2015
- 2015-05-07 US US15/309,470 patent/US10004711B2/en active Active
- 2015-05-07 KR KR1020167034149A patent/KR102399290B1/ko active Active
- 2015-05-07 BR BR112016026143A patent/BR112016026143A2/pt not_active Application Discontinuation
- 2015-05-07 JP JP2016566933A patent/JP6819957B2/ja not_active Expired - Fee Related
- 2015-05-07 EP EP15789367.8A patent/EP3139741A4/en not_active Withdrawn
- 2015-05-07 CN CN201580036769.1A patent/CN106470547B/zh not_active Expired - Fee Related
- 2015-05-07 WO PCT/US2015/029790 patent/WO2015171960A1/en not_active Ceased
- 2015-05-08 TW TW104114736A patent/TWI743022B/zh not_active IP Right Cessation
Non-Patent Citations (4)
| Title |
|---|
| Biomed. Research, 28(5), 261-266, 2007.* |
| Innate Immunity, 18(3), 429-327, 2012.* |
| J. Argic. Food Chem., 59, 2627-2635, 2011. |
| Scientific Papers, Animal Science and Biotechnologies. 44(2), 108-118, 2011.* |
Also Published As
| Publication number | Publication date |
|---|---|
| US10004711B2 (en) | 2018-06-26 |
| CN106470547B (zh) | 2020-10-09 |
| EP3139741A1 (en) | 2017-03-15 |
| JP6819957B2 (ja) | 2021-01-27 |
| WO2015171960A1 (en) | 2015-11-12 |
| CN106470547A (zh) | 2017-03-01 |
| KR20170003637A (ko) | 2017-01-09 |
| BR112016026143A2 (pt) | 2018-08-07 |
| US20170181995A1 (en) | 2017-06-29 |
| JP2017514874A (ja) | 2017-06-08 |
| TW201622717A (zh) | 2016-07-01 |
| EP3139741A4 (en) | 2017-11-29 |
| TWI743022B (zh) | 2021-10-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR102399290B1 (ko) | 10-하이드록시-2-데센산을 포함하는 방법 및 조성물 | |
| Romanova et al. | Evaluation of the content of polyunsaturated fatty acids in artemia at different stages of ontogenesis | |
| Kapoor et al. | Dietary polyunsaturated fatty acids (PUFAs): Uses and potential health benefits | |
| Wu et al. | Curcumin boosts DHA in the brain: Implications for the prevention of anxiety disorders | |
| Al-Khalaifah | Modulatory effect of dietary polyunsaturated fatty acids on immunity, represented by phagocytic activity | |
| Crupi et al. | n-3 fatty acids: role in neurogenesis and neuroplasticity | |
| Pottel et al. | Omega-3 fatty acids: physiology, biological sources and potential applications in supportive cancer care | |
| JP2014195460A (ja) | 乳幼児用調合乳におけるＤＰＡ（ｎ−６）油の使用 | |
| EA035287B1 (ru) | Микроорганизмы, продуцирующие эйкозапентаеновую кислоту, композиции, содержащие жирные кислоты, и способы их получения и применения | |
| Baker et al. | Recognizing the Health Benefits of Plant‐Sourced Omega‐3 Stearidonic Acid: Exploring Its Complementary Role to Preformed EPA/DHA | |
| US20200009099A1 (en) | Compositions and methods for the prevention and/or treatment of schistosomiasis | |
| Alva et al. | Bridging the Gap: Investigating the Interplay of Polyunsaturated Fatty Acids and Osteoporosis | |
| Jeong et al. | Lipid and fatty acid composition in Nannochloropsis oculata cultured in varying salinities | |
| AL-KHALAIFAH et al. | Fatty Acids and Immune Function | |
| Calder | Marine omega-3 fatty acids and inflammation | |
| Sartaj et al. | Production of Omega‐3 and Omega‐6 PUFA from Food Crops and Fishes | |
| Al-Khalaifah | Lipids as Main Constitutes of Biological Cells | |
| Ouyang et al. | Resources and bioactivities of polyunsaturated fatty acids | |
| Эргашева et al. | OMEGA-3 AND BIOCHEMICAL PROCESSES OF INFLAMMATION IN THE BODY | |
| MUANGKEOW | Effect of feeding soybean and palm blended oil on laying performance and egg quality | |
| Singh et al. | 3 BiotechnologicalofAlgaein Pharmaceuticals Application Industries with Special Reference to Omega-3 Fatty Acid and Human Health | |
| Weng | Immunomodulation by dietary lipids: Soybean oil, menhaden fish oil, chicken fat, and hydrogenated soybean oil in Japanese quail (Coturnix coturnix japonica) and bobwhite quail (Colinus virginianus) | |
| Volker | Fat manipulation in the treatment of rheumatoid arthritis: a review | |
| Rubio et al. | Omegas: Pharmaceutical high value products and one of the most functional bioactive compounds | |
| WAH | Growth Profile and Lipid Composition of Locally Isolated Benthic Diatom Amphora Subacutiuscula (Schoeman, 1972) Under Different Cultivation Conditions |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20161206 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| A201 | Request for examination | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 20200406 Comment text: Request for Examination of Application |
|
| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 20210503 Patent event code: PE09021S01D |
|
| E701 | Decision to grant or registration of patent right | ||
| PE0701 | Decision of registration |
Patent event code: PE07011S01D Comment text: Decision to Grant Registration Patent event date: 20220302 |
|
| GRNT | Written decision to grant | ||
| PR0701 | Registration of establishment |
Comment text: Registration of Establishment Patent event date: 20220513 Patent event code: PR07011E01D |
|
| PR1002 | Payment of registration fee |
Payment date: 20220513 End annual number: 3 Start annual number: 1 |
|
| PG1601 | Publication of registration |