JP2020526493A5 - - Google Patents
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- JP2020526493A5 JP2020526493A5 JP2019572023A JP2019572023A JP2020526493A5 JP 2020526493 A5 JP2020526493 A5 JP 2020526493A5 JP 2019572023 A JP2019572023 A JP 2019572023A JP 2019572023 A JP2019572023 A JP 2019572023A JP 2020526493 A5 JP2020526493 A5 JP 2020526493A5
- Authority
- JP
- Japan
- Prior art keywords
- chemically sulfated
- bioconjugate
- peptide
- glycan
- chemically
- 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.)
- Pending
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- 108090000765 processed proteins & peptides Proteins 0.000 claims description 65
- 150000004676 glycans Chemical class 0.000 claims description 52
- 238000000034 method Methods 0.000 claims description 24
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 18
- 206010016654 Fibrosis Diseases 0.000 claims description 14
- 201000010099 disease Diseases 0.000 claims description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
- 230000004761 fibrosis Effects 0.000 claims description 14
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 14
- 235000001014 amino acid Nutrition 0.000 claims description 12
- 150000001413 amino acids Chemical class 0.000 claims description 12
- -1 sulfated carboxymethyl alginate Chemical compound 0.000 claims description 12
- 102000008186 Collagen Human genes 0.000 claims description 10
- 108010035532 Collagen Proteins 0.000 claims description 10
- 229920001436 collagen Polymers 0.000 claims description 10
- 230000003176 fibrotic effect Effects 0.000 claims description 10
- 229920002971 Heparan sulfate Polymers 0.000 claims description 8
- 150000002016 disaccharides Chemical class 0.000 claims description 8
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims description 8
- 125000006850 spacer group Chemical group 0.000 claims description 8
- 238000007306 functionalization reaction Methods 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 7
- 239000004475 Arginine Substances 0.000 claims description 6
- 239000012190 activator Substances 0.000 claims description 6
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 6
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims description 6
- 230000019635 sulfation Effects 0.000 claims description 5
- 238000005670 sulfation reaction Methods 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 class 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
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 claims description 4
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims description 4
- 229920002307 Dextran Polymers 0.000 claims description 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 4
- 239000004471 Glycine Substances 0.000 claims description 4
- 241000711549 Hepacivirus C Species 0.000 claims description 4
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical class OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 claims description 4
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims description 4
- 230000009787 cardiac fibrosis Effects 0.000 claims description 4
- 238000005859 coupling reaction Methods 0.000 claims description 4
- 229960002086 dextran Drugs 0.000 claims description 4
- 229960000633 dextran sulfate Drugs 0.000 claims description 4
- 229920002674 hyaluronan Polymers 0.000 claims description 4
- 229960003160 hyaluronic acid Drugs 0.000 claims description 4
- 208000015181 infectious disease Diseases 0.000 claims description 4
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims description 4
- 201000002793 renal fibrosis Diseases 0.000 claims description 4
- FPIRBHDGWMWJEP-UHFFFAOYSA-N 1-hydroxy-7-azabenzotriazole Chemical compound C1=CN=C2N(O)N=NC2=C1 FPIRBHDGWMWJEP-UHFFFAOYSA-N 0.000 claims description 3
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims description 2
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 claims description 2
- WPGCGXIZQYAXHI-JIZZDEOASA-N 2-aminoacetic acid;(2s)-2-amino-3-hydroxypropanoic acid Chemical compound NCC(O)=O.NCC(O)=O.OC[C@H](N)C(O)=O WPGCGXIZQYAXHI-JIZZDEOASA-N 0.000 claims description 2
- JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 claims description 2
- SQDAZGGFXASXDW-UHFFFAOYSA-N 5-bromo-2-(trifluoromethoxy)pyridine Chemical class FC(F)(F)OC1=CC=C(Br)C=N1 SQDAZGGFXASXDW-UHFFFAOYSA-N 0.000 claims description 2
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical class O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 claims description 2
- 206010003827 Autoimmune hepatitis Diseases 0.000 claims description 2
- 208000008439 Biliary Liver Cirrhosis Diseases 0.000 claims description 2
- 208000033222 Biliary cirrhosis primary Diseases 0.000 claims description 2
- 206010008609 Cholangitis sclerosing Diseases 0.000 claims description 2
- 229920002567 Chondroitin Polymers 0.000 claims description 2
- 229920001287 Chondroitin sulfate Polymers 0.000 claims description 2
- 206010060774 Chondrosis Diseases 0.000 claims description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 2
- 208000011231 Crohn disease Diseases 0.000 claims description 2
- 201000003883 Cystic fibrosis Diseases 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 208000024720 Fabry Disease Diseases 0.000 claims description 2
- 208000015872 Gaucher disease Diseases 0.000 claims description 2
- 208000018565 Hemochromatosis Diseases 0.000 claims description 2
- 206010019668 Hepatic fibrosis Diseases 0.000 claims description 2
- 241000700721 Hepatitis B virus Species 0.000 claims description 2
- 208000024934 IgG4-related mediastinitis Diseases 0.000 claims description 2
- 208000014919 IgG4-related retroperitoneal fibrosis Diseases 0.000 claims description 2
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 2
- 239000004472 Lysine Substances 0.000 claims description 2
- 208000002805 Mediastinal fibrosis Diseases 0.000 claims description 2
- 208000002678 Mucopolysaccharidoses Diseases 0.000 claims description 2
- 206010028594 Myocardial fibrosis Diseases 0.000 claims description 2
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 claims description 2
- 208000014060 Niemann-Pick disease Diseases 0.000 claims description 2
- 208000012654 Primary biliary cholangitis Diseases 0.000 claims description 2
- 206010036805 Progressive massive fibrosis Diseases 0.000 claims description 2
- 206010038979 Retroperitoneal fibrosis Diseases 0.000 claims description 2
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims description 2
- 201000009594 Systemic Scleroderma Diseases 0.000 claims description 2
- 206010042953 Systemic sclerosis Diseases 0.000 claims description 2
- 239000000853 adhesive Substances 0.000 claims description 2
- 230000001070 adhesive effect Effects 0.000 claims description 2
- 235000004279 alanine Nutrition 0.000 claims description 2
- 229940072056 alginate Drugs 0.000 claims description 2
- 229920000615 alginic acid Polymers 0.000 claims description 2
- 235000010443 alginic acid Nutrition 0.000 claims description 2
- 208000006682 alpha 1-Antitrypsin Deficiency Diseases 0.000 claims description 2
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 2
- 206010003246 arthritis Diseases 0.000 claims description 2
- 230000001746 atrial effect Effects 0.000 claims description 2
- 150000001718 carbodiimides Chemical group 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- DLGJWSVWTWEWBJ-HGGSSLSASA-N chondroitin Chemical class CC(O)=N[C@@H]1[C@H](O)O[C@H](CO)[C@H](O)[C@@H]1OC1[C@H](O)[C@H](O)C=C(C(O)=O)O1 DLGJWSVWTWEWBJ-HGGSSLSASA-N 0.000 claims description 2
- 229940059329 chondroitin sulfate Drugs 0.000 claims description 2
- 230000001684 chronic effect Effects 0.000 claims description 2
- 230000008602 contraction Effects 0.000 claims description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 2
- GICLSALZHXCILJ-UHFFFAOYSA-N ctk5a5089 Chemical compound NCC(O)=O.NCC(O)=O GICLSALZHXCILJ-UHFFFAOYSA-N 0.000 claims description 2
- 238000010494 dissociation reaction Methods 0.000 claims description 2
- 230000005593 dissociations Effects 0.000 claims description 2
- 229920000669 heparin Polymers 0.000 claims description 2
- 229960002897 heparin Drugs 0.000 claims description 2
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 claims description 2
- 150000002772 monosaccharides Chemical class 0.000 claims description 2
- 206010028093 mucopolysaccharidosis Diseases 0.000 claims description 2
- 201000002273 mucopolysaccharidosis II Diseases 0.000 claims description 2
- 208000022018 mucopolysaccharidosis type 2 Diseases 0.000 claims description 2
- 208000010125 myocardial infarction Diseases 0.000 claims description 2
- 210000005036 nerve Anatomy 0.000 claims description 2
- 239000012434 nucleophilic reagent Substances 0.000 claims description 2
- 201000000742 primary sclerosing cholangitis Diseases 0.000 claims description 2
- 208000005069 pulmonary fibrosis Diseases 0.000 claims description 2
- 208000010157 sclerosing cholangitis Diseases 0.000 claims description 2
- 230000009885 systemic effect Effects 0.000 claims description 2
- 208000010412 Glaucoma Diseases 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 201000007270 liver cancer Diseases 0.000 claims 2
- 208000014018 liver neoplasm Diseases 0.000 claims 2
- 201000006417 multiple sclerosis Diseases 0.000 claims 2
- 230000004770 neurodegeneration Effects 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 210000004899 c-terminal region Anatomy 0.000 claims 1
- 230000001180 sulfating effect Effects 0.000 claims 1
- 210000004024 hepatic stellate cell Anatomy 0.000 description 5
- 229940125904 compound 1 Drugs 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 1
- 150000001720 carbohydrates Chemical group 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2023032277A JP2023065600A (ja) | 2017-07-07 | 2023-03-02 | 化学的に修飾された主鎖を有するバイオコンジュゲート |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762530066P | 2017-07-07 | 2017-07-07 | |
| US62/530,066 | 2017-07-07 | ||
| PCT/US2018/041280 WO2019010490A1 (en) | 2017-07-07 | 2018-07-09 | BIOCONJUGATES WITH CHEMICALLY MODIFIED SKELETONS |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2023032277A Division JP2023065600A (ja) | 2017-07-07 | 2023-03-02 | 化学的に修飾された主鎖を有するバイオコンジュゲート |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2020526493A JP2020526493A (ja) | 2020-08-31 |
| JP2020526493A5 true JP2020526493A5 (enExample) | 2021-08-19 |
Family
ID=64950399
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019572023A Pending JP2020526493A (ja) | 2017-07-07 | 2018-07-09 | 化学的に修飾された主鎖を有するバイオコンジュゲート |
| JP2023032277A Pending JP2023065600A (ja) | 2017-07-07 | 2023-03-02 | 化学的に修飾された主鎖を有するバイオコンジュゲート |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2023032277A Pending JP2023065600A (ja) | 2017-07-07 | 2023-03-02 | 化学的に修飾された主鎖を有するバイオコンジュゲート |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US11896642B2 (enExample) |
| EP (1) | EP3648775A4 (enExample) |
| JP (2) | JP2020526493A (enExample) |
| KR (1) | KR20200026918A (enExample) |
| CN (1) | CN111050778B (enExample) |
| AU (1) | AU2018298226B2 (enExample) |
| WO (1) | WO2019010490A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3142684A4 (en) | 2014-05-12 | 2018-05-23 | Purdue Research Foundation | Selectin and icam/vcam peptide ligand conjugates |
| AU2018298224B2 (en) | 2017-07-07 | 2024-08-15 | Symic Ip, Llc | Synthetic bioconjugates |
| WO2022227225A1 (zh) * | 2021-04-27 | 2022-11-03 | 北京博辉瑞进生物科技有限公司 | 一种嵌合肽修饰的sis膜、其制备方法及应用 |
| CN113754795B (zh) * | 2021-10-19 | 2023-03-10 | 澳门大学 | 磺酸化透明质酸类化合物、其制备方法及其应用 |
| CN115040535B (zh) * | 2022-08-15 | 2022-12-16 | 华南理工大学 | 硫酸化透明质酸在制备预防角膜纤维化、角膜瘢痕滴眼液中的应用 |
| JP7725041B2 (ja) * | 2023-07-26 | 2025-08-19 | 株式会社高研 | コラーゲン結合型膜透過性ペプチド、並びに、該ペプチド及びコラーゲン若しくはコラーゲン誘導体を含む運搬体 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ITPD940054A1 (it) * | 1994-03-23 | 1995-09-23 | Fidia Advanced Biopolymers Srl | Polisaccaridi solfatati |
| LT2280720T (lt) * | 2008-03-27 | 2019-07-25 | Purdue Research Foundation | Kolageną surišantys sintetiniai peptidoglikanai, jų paruošimas ir naudojimo būdai |
| WO2010129547A1 (en) | 2009-05-04 | 2010-11-11 | Purdue Research Foundation | Collagen-binding synthetic peptidoglycans for wound healing |
| US9173919B2 (en) | 2011-02-16 | 2015-11-03 | Purdue Research Foundation | Collagen-targeted nanoparticles |
| SG195114A1 (en) | 2011-05-24 | 2013-12-30 | Purdue Research Foundation | Hyaluronic acid-binding synthetic peptidoglycans, preparation, and methods of use |
| EP2970509B1 (en) * | 2013-03-15 | 2020-05-13 | Purdue Research Foundation | Extracellular matrix-binding synthetic peptidoglycans |
| US10772931B2 (en) | 2014-04-25 | 2020-09-15 | Purdue Research Foundation | Collagen binding synthetic peptidoglycans for treatment of endothelial dysfunction |
| EP3142684A4 (en) | 2014-05-12 | 2018-05-23 | Purdue Research Foundation | Selectin and icam/vcam peptide ligand conjugates |
| WO2016061145A1 (en) | 2014-10-13 | 2016-04-21 | Symic Biomedical, Inc. | Synthetic proteoglycans for preventing tissue adhesion |
| WO2016061147A1 (en) | 2014-10-13 | 2016-04-21 | John Eric Paderi | Luminal vessel coating for arteriovenous fistula |
| WO2016065083A1 (en) | 2014-10-21 | 2016-04-28 | Symic Biomedical, Inc. | Peptidoglycans comprising collagen-binding peptides for treating gastroesophageal injury |
| WO2016111651A1 (en) * | 2015-01-09 | 2016-07-14 | Agency For Science, Technology And Research | Pdgf-b /pdgf-bb binding variants of heparan sulphates |
| WO2016161333A2 (en) | 2015-04-01 | 2016-10-06 | Purdue Research Foundation | Compositions comprising bioconjugates |
| CN107771085B (zh) * | 2015-04-17 | 2024-09-03 | 斯米克控股(美国)有限公司 | 生物缀合物及其用途 |
| US20170112941A1 (en) | 2015-10-13 | 2017-04-27 | Symic Ip, Llc | Ve-cadherin binding bioconjugate |
| AU2018298224B2 (en) | 2017-07-07 | 2024-08-15 | Symic Ip, Llc | Synthetic bioconjugates |
| WO2019010485A1 (en) | 2017-07-07 | 2019-01-10 | Symic Ip, Llc | TREATMENT OF FIBROSIS |
-
2018
- 2018-07-09 US US16/629,183 patent/US11896642B2/en active Active
- 2018-07-09 KR KR1020207002776A patent/KR20200026918A/ko not_active Ceased
- 2018-07-09 WO PCT/US2018/041280 patent/WO2019010490A1/en not_active Ceased
- 2018-07-09 JP JP2019572023A patent/JP2020526493A/ja active Pending
- 2018-07-09 EP EP18827869.1A patent/EP3648775A4/en active Pending
- 2018-07-09 CN CN201880043683.5A patent/CN111050778B/zh active Active
- 2018-07-09 AU AU2018298226A patent/AU2018298226B2/en not_active Expired - Fee Related
-
2023
- 2023-03-02 JP JP2023032277A patent/JP2023065600A/ja active Pending
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