JP2018534324A5 - - Google Patents
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- Publication number
- JP2018534324A5 JP2018534324A5 JP2018526129A JP2018526129A JP2018534324A5 JP 2018534324 A5 JP2018534324 A5 JP 2018534324A5 JP 2018526129 A JP2018526129 A JP 2018526129A JP 2018526129 A JP2018526129 A JP 2018526129A JP 2018534324 A5 JP2018534324 A5 JP 2018534324A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- aryl
- group
- oxy
- heptamethyl
- 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.)
- Granted
Links
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 29
- 150000001875 compounds Chemical class 0.000 claims description 25
- -1 therefore Chemical group 0.000 claims description 19
- 208000023504 respiratory system disease Diseases 0.000 claims description 13
- 206010035664 Pneumonia Diseases 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- 201000003883 Cystic fibrosis Diseases 0.000 claims description 11
- 230000001684 chronic effect Effects 0.000 claims description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- UOBYKYZJUGYBDK-UHFFFAOYSA-M 2-naphthoate Chemical compound C1=CC=CC2=CC(C(=O)[O-])=CC=C21 UOBYKYZJUGYBDK-UHFFFAOYSA-M 0.000 claims description 8
- ZQVKTHRQIXSMGY-UHFFFAOYSA-M 4-ethylbenzoate Chemical compound CCC1=CC=C(C([O-])=O)C=C1 ZQVKTHRQIXSMGY-UHFFFAOYSA-M 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 208000004756 Respiratory Insufficiency Diseases 0.000 claims description 6
- 230000007774 longterm Effects 0.000 claims description 6
- 206010062952 diffuse panbronchiolitis Diseases 0.000 claims description 5
- QRWZFUBHOQWUGH-UHFFFAOYSA-N 2,5-dimethylpyrazole-3-carboxylic acid Chemical compound CC=1C=C(C(O)=O)N(C)N=1 QRWZFUBHOQWUGH-UHFFFAOYSA-N 0.000 claims description 4
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 claims description 4
- QZLSBOVWPHXCLT-UHFFFAOYSA-N 5-chlorothiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=C(Cl)S1 QZLSBOVWPHXCLT-UHFFFAOYSA-N 0.000 claims description 4
- 241000700605 Viruses Species 0.000 claims description 4
- 208000006673 asthma Diseases 0.000 claims description 4
- DJXNJVFEFSWHLY-UHFFFAOYSA-M quinoline-3-carboxylate Chemical compound C1=CC=CC2=CC(C(=O)[O-])=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-M 0.000 claims description 4
- 206010066091 Bronchial Hyperreactivity Diseases 0.000 claims description 3
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 3
- 206010010356 Congenital anomaly Diseases 0.000 claims description 3
- 206010038678 Respiratory depression Diseases 0.000 claims description 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 3
- 238000002512 chemotherapy Methods 0.000 claims description 3
- 208000029771 childhood onset asthma Diseases 0.000 claims description 3
- 230000002232 neuromuscular Effects 0.000 claims description 3
- 230000002085 persistent effect Effects 0.000 claims description 3
- 201000004193 respiratory failure Diseases 0.000 claims description 3
- 208000011580 syndromic disease Diseases 0.000 claims description 3
- 238000002054 transplantation Methods 0.000 claims description 3
- 206010006458 Bronchitis chronic Diseases 0.000 claims description 2
- 241000342334 Human metapneumovirus Species 0.000 claims description 2
- 206010006451 bronchitis Diseases 0.000 claims description 2
- 208000007451 chronic bronchitis Diseases 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 39
- 125000003118 aryl group Chemical group 0.000 claims 30
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 18
- 229910052736 halogen Inorganic materials 0.000 claims 13
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 11
- 150000002367 halogens Chemical class 0.000 claims 11
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 10
- 150000001408 amides Chemical class 0.000 claims 9
- 150000002148 esters Chemical class 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 9
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims 7
- 125000001424 substituent group Chemical group 0.000 claims 7
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims 6
- 125000005842 heteroatom Chemical group 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 4
- 229920001577 copolymer Chemical group 0.000 claims 4
- 210000000981 epithelium Anatomy 0.000 claims 4
- 239000012453 solvate Substances 0.000 claims 4
- 125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 230000004890 epithelial barrier function Effects 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical class NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 2
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 2
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims 2
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 2
- 230000001548 androgenic effect Effects 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 150000005676 cyclic carbonates Chemical class 0.000 claims 2
- 230000007547 defect Effects 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 210000002919 epithelial cell Anatomy 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 210000002345 respiratory system Anatomy 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 206010006448 Bronchiolitis Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 208000032571 Infant acute respiratory distress syndrome Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 206010028974 Neonatal respiratory distress syndrome Diseases 0.000 claims 1
- 208000037656 Respiratory Sounds Diseases 0.000 claims 1
- 206010047924 Wheezing Diseases 0.000 claims 1
- 210000000621 bronchi Anatomy 0.000 claims 1
- 230000036427 bronchial hyperreactivity Effects 0.000 claims 1
- 201000009267 bronchiectasis Diseases 0.000 claims 1
- 210000003123 bronchiole Anatomy 0.000 claims 1
- 206010006475 bronchopulmonary dysplasia Diseases 0.000 claims 1
- 208000027157 chronic rhinosinusitis Diseases 0.000 claims 1
- 208000037765 diseases and disorders Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 230000028709 inflammatory response Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000005185 naphthylcarbonyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 claims 1
- 125000005146 naphthylsulfonyl group Chemical group C1(=CC=CC2=CC=CC=C12)S(=O)(=O)* 0.000 claims 1
- 210000003928 nasal cavity Anatomy 0.000 claims 1
- 201000002652 newborn respiratory distress syndrome Diseases 0.000 claims 1
- 210000001331 nose Anatomy 0.000 claims 1
- 210000003695 paranasal sinus Anatomy 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 210000003800 pharynx Anatomy 0.000 claims 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000005400 pyridylcarbonyl group Chemical group N1=C(C=CC=C1)C(=O)* 0.000 claims 1
- 230000029058 respiratory gaseous exchange Effects 0.000 claims 1
- 230000009885 systemic effect Effects 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 210000003437 trachea Anatomy 0.000 claims 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 4
- 206010067472 Organising pneumonia Diseases 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 201000009805 cryptogenic organizing pneumonia Diseases 0.000 description 4
- 230000000241 respiratory effect Effects 0.000 description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- FNCJTSIUDNMKLD-UHFFFAOYSA-N 1-oxa-6-azacyclopentadec-8-yl morpholine-4-carboxylate Chemical compound N1(CCOCC1)C(=O)OC1CNCCCCOCCCCCCC1 FNCJTSIUDNMKLD-UHFFFAOYSA-N 0.000 description 2
- GHICCUXQJBDNRN-UHFFFAOYSA-M 4-iodobenzoate Chemical compound [O-]C(=O)C1=CC=C(I)C=C1 GHICCUXQJBDNRN-UHFFFAOYSA-M 0.000 description 2
- 0 CC[C@]([C@@](C)(*)[C@](C)[C@@](C)N(C)C[C@](C)C[C@@](C)(*)[C@@]([C@@](C)[C@@](*)[C@]1C=*)*#C)OC1=O Chemical compound CC[C@]([C@@](C)(*)[C@](C)[C@@](C)N(C)C[C@](C)C[C@@](C)(*)[C@@]([C@@](C)[C@@](*)[C@]1C=*)*#C)OC1=O 0.000 description 2
- 230000005856 abnormality Effects 0.000 description 2
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-M nicotinate Chemical compound [O-]C(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-M 0.000 description 2
- 230000000414 obstructive effect Effects 0.000 description 2
- 201000009890 sinusitis Diseases 0.000 description 2
- 206010058314 Dysplasia Diseases 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 238000009093 first-line therapy Methods 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1520419.1 | 2015-11-19 | ||
| GBGB1520419.1A GB201520419D0 (en) | 2015-11-19 | 2015-11-19 | Compounds |
| PCT/EP2016/078360 WO2017085329A1 (en) | 2015-11-19 | 2016-11-21 | Azithromycin derivatives with epithelial barrier enhancement properties |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021019109A Division JP7256558B2 (ja) | 2015-11-19 | 2021-02-09 | 上皮バリア機能増強特性を有するアジスロマイシン誘導体 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018534324A JP2018534324A (ja) | 2018-11-22 |
| JP2018534324A5 true JP2018534324A5 (https=) | 2021-01-28 |
| JP6849896B2 JP6849896B2 (ja) | 2021-03-31 |
Family
ID=55133040
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018526129A Active JP6849896B2 (ja) | 2015-11-19 | 2016-11-21 | 上皮バリア機能増強特性を有するアジスロマイシン誘導体 |
| JP2021019109A Active JP7256558B2 (ja) | 2015-11-19 | 2021-02-09 | 上皮バリア機能増強特性を有するアジスロマイシン誘導体 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021019109A Active JP7256558B2 (ja) | 2015-11-19 | 2021-02-09 | 上皮バリア機能増強特性を有するアジスロマイシン誘導体 |
Country Status (19)
| Country | Link |
|---|---|
| US (3) | US10723752B2 (https=) |
| EP (2) | EP3377511B1 (https=) |
| JP (2) | JP6849896B2 (https=) |
| KR (2) | KR20240157138A (https=) |
| CN (2) | CN108290919B (https=) |
| CA (1) | CA3005088A1 (https=) |
| CY (1) | CY1123418T1 (https=) |
| DK (1) | DK3377511T3 (https=) |
| ES (1) | ES2810703T3 (https=) |
| GB (1) | GB201520419D0 (https=) |
| HR (1) | HRP20201246T1 (https=) |
| HU (1) | HUE050307T2 (https=) |
| LT (1) | LT3377511T (https=) |
| PL (1) | PL3377511T3 (https=) |
| PT (1) | PT3377511T (https=) |
| RS (1) | RS60698B1 (https=) |
| SI (1) | SI3377511T1 (https=) |
| SM (1) | SMT202000426T1 (https=) |
| WO (1) | WO2017085329A1 (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201520419D0 (en) | 2015-11-19 | 2016-01-06 | Epi Endo Pharmaceuticals Ehf | Compounds |
| KR20220156570A (ko) | 2020-03-12 | 2022-11-25 | 조에티스 서비시즈 엘엘씨 | 면역조절성 유레아 아잘라이드 |
| AU2022343476B2 (en) * | 2021-09-07 | 2025-02-20 | Zoetis Services Llc | Immunomodulating azalides |
| CN121038797A (zh) | 2023-03-22 | 2025-11-28 | 艾比恩多制药有限责任公司 | 用于治疗嗜酸性粒细胞相关疾病的阿奇霉素衍生物 |
| GB202404587D0 (en) | 2024-03-28 | 2024-05-15 | Epiendo Pharmaceuticals Ehf | Chemical forms |
| GB202412461D0 (en) | 2024-08-23 | 2024-10-09 | Epiendo Pharmaceuticals Ehf | Medial use |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3725385A (en) | 1970-11-02 | 1973-04-03 | Abbott Lab | Process for the demethylation of 3-amino macrolides |
| HRP20010018A2 (en) * | 2001-01-09 | 2002-12-31 | Pliva D D | Novel anti-inflammatory compounds |
| AU2003219770B2 (en) * | 2002-02-15 | 2008-10-09 | Merckle Gmbh | Conjugates of biologically active compounds, methods for their preparation and use, formulation and pharmaceutical applications thereof |
| RU2330858C2 (ru) | 2002-07-08 | 2008-08-10 | Глаксомитклайн Истраживацки Центар Загреб Д.О.О. | Новые соединения, составы и способы лечения воспалительных заболеваний и состояний |
| ITMI20022292A1 (it) | 2002-10-29 | 2004-04-30 | Zambon Spa | 9a-azalidi ad attivita' antiinfiammatoria. |
| GB0310984D0 (en) * | 2003-05-13 | 2003-06-18 | Glaxo Group Ltd | Novel compounds |
| US7767797B1 (en) * | 2004-09-30 | 2010-08-03 | Synovo Gmbh | Macrocyclic compounds and methods of use thereof |
| PT1851236E (pt) | 2005-01-13 | 2010-10-25 | Glaxosmithkline Zagreb | Macrólidos com actividade anti-inflamatória |
| EP1841776B1 (en) * | 2005-01-13 | 2008-12-31 | GlaxoSmithKline istrazivacki centar Zagreb d.o.o. | Decladinosyl-macrolides with anti-inflammatory activity |
| CN1837225A (zh) | 2005-08-23 | 2006-09-27 | 济南思创生物技术有限公司 | 阿奇霉素衍生物及其制法和药物应用 |
| RU2455308C2 (ru) | 2006-05-01 | 2012-07-10 | Тайсо Фармасьютикал Ко., Лтд. | Макролидные производные |
| CN101074251B (zh) * | 2007-06-22 | 2011-06-15 | 山东大学 | 阿奇霉素4＂-氨甲酸酯衍生物、制备方法及其药物组合物 |
| WO2009006403A2 (en) * | 2007-06-29 | 2009-01-08 | Georgia Tech Research Corporation | Non-peptide macrocyclic histone deacetylase (hdac) inhibitors and methods of making and using thereof |
| WO2010086351A1 (en) * | 2009-01-30 | 2010-08-05 | Glaxosmithkline Istrazivacki Centar Zagreb D.O.O. | 3'-n-substituted 9-deoxo-9a-methyl-9a-aza-homoerythromycin having antimalarial activity |
| CA2814333A1 (en) * | 2010-10-10 | 2012-04-19 | Synovo Gmbh | Anti-inflammatory macrolides |
| GB201105633D0 (en) * | 2011-04-01 | 2011-05-18 | Norbrook Lab Ltd | Antibotic compounds |
| EP2831083A4 (en) * | 2012-03-27 | 2016-03-09 | Michael W Burnet | INFLAMMATORY MAKROLIDE |
| AU2014252462A1 (en) | 2013-04-10 | 2015-10-01 | Probiotic Pharmaceuticals Aps | Azithromycin antimicrobial derivatives with non-antibiotic pharmaceutical effect |
| GB201520419D0 (en) | 2015-11-19 | 2016-01-06 | Epi Endo Pharmaceuticals Ehf | Compounds |
-
2015
- 2015-11-19 GB GBGB1520419.1A patent/GB201520419D0/en not_active Ceased
-
2016
- 2016-11-21 KR KR1020247035784A patent/KR20240157138A/ko active Pending
- 2016-11-21 JP JP2018526129A patent/JP6849896B2/ja active Active
- 2016-11-21 KR KR1020187017001A patent/KR102724114B1/ko active Active
- 2016-11-21 HR HRP20201246TT patent/HRP20201246T1/hr unknown
- 2016-11-21 CN CN201680067151.6A patent/CN108290919B/zh active Active
- 2016-11-21 RS RS20200947A patent/RS60698B1/sr unknown
- 2016-11-21 WO PCT/EP2016/078360 patent/WO2017085329A1/en not_active Ceased
- 2016-11-21 CN CN202210535850.6A patent/CN114933620B/zh active Active
- 2016-11-21 LT LTEP16804720.7T patent/LT3377511T/lt unknown
- 2016-11-21 DK DK16804720.7T patent/DK3377511T3/da active
- 2016-11-21 EP EP16804720.7A patent/EP3377511B1/en active Active
- 2016-11-21 US US15/777,223 patent/US10723752B2/en active Active
- 2016-11-21 SM SM20200426T patent/SMT202000426T1/it unknown
- 2016-11-21 HU HUE16804720A patent/HUE050307T2/hu unknown
- 2016-11-21 EP EP20172534.8A patent/EP3708573A1/en active Pending
- 2016-11-21 ES ES16804720T patent/ES2810703T3/es active Active
- 2016-11-21 SI SI201630881T patent/SI3377511T1/sl unknown
- 2016-11-21 PL PL16804720T patent/PL3377511T3/pl unknown
- 2016-11-21 CA CA3005088A patent/CA3005088A1/en active Pending
- 2016-11-21 PT PT168047207T patent/PT3377511T/pt unknown
-
2020
- 2020-06-18 US US16/904,593 patent/US11236120B2/en active Active
- 2020-08-12 CY CY20201100750T patent/CY1123418T1/el unknown
-
2021
- 2021-02-09 JP JP2021019109A patent/JP7256558B2/ja active Active
- 2021-12-15 US US17/551,223 patent/US12049477B2/en active Active
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