JP6155285B2 - Ｈｉｖ成熟阻害活性のあるｃ−３シクロアルケニルトリテルペノイド - Google Patents
Ｈｉｖ成熟阻害活性のあるｃ−３シクロアルケニルトリテルペノイド Download PDFInfo
- Publication number
- JP6155285B2 JP6155285B2 JP2014557739A JP2014557739A JP6155285B2 JP 6155285 B2 JP6155285 B2 JP 6155285B2 JP 2014557739 A JP2014557739 A JP 2014557739A JP 2014557739 A JP2014557739 A JP 2014557739A JP 6155285 B2 JP6155285 B2 JP 6155285B2
- Authority
- JP
- Japan
- Prior art keywords
- mmol
- cyclopenta
- pentamethyl
- prop
- mixture
- 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.)
- Expired - Fee Related
Links
- 0 CC*1CC*(C)CC1 Chemical compound CC*1CC*(C)CC1 0.000 description 19
- SQVIHGWRHKZSSZ-BEUFMZLVSA-N CC(C)([C@@H]1CC2)C(C(CC3)=CCC3C(OC)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21NCCN(CC1)CCS1(=O)=O Chemical compound CC(C)([C@@H]1CC2)C(C(CC3)=CCC3C(OC)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21NCCN(CC1)CCS1(=O)=O SQVIHGWRHKZSSZ-BEUFMZLVSA-N 0.000 description 1
- RJICCGAYPNRWSE-CNRMHUMKSA-N CC(C)([C@@H]1CC2)C(OS(C(F)(F)F)(=O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C=O Chemical compound CC(C)([C@@H]1CC2)C(OS(C(F)(F)F)(=O)=O)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21C=O RJICCGAYPNRWSE-CNRMHUMKSA-N 0.000 description 1
- LZQGOWADPPJPOC-UHFFFAOYSA-N CC(C)OC(CC1)=CCC1(CCO1)C1=O Chemical compound CC(C)OC(CC1)=CCC1(CCO1)C1=O LZQGOWADPPJPOC-UHFFFAOYSA-N 0.000 description 1
- BQCGGEWGJCVMTQ-JOYZNUJKSA-N CC(C)[C@H](CC1)[C@H]([C@@H](CC2)[C@@](C)(CC3)C(CC4)[C@H]2[C@]2(C)[C@@H]4C(C)(C)C(C(CC4)CCC4(C(OC(C)C)=O)C(OC(C)C)=O)=CC2)[C@]13NCCN(CC1)CCS1(=O)=O Chemical compound CC(C)[C@H](CC1)[C@H]([C@@H](CC2)[C@@](C)(CC3)C(CC4)[C@H]2[C@]2(C)[C@@H]4C(C)(C)C(C(CC4)CCC4(C(OC(C)C)=O)C(OC(C)C)=O)=CC2)[C@]13NCCN(CC1)CCS1(=O)=O BQCGGEWGJCVMTQ-JOYZNUJKSA-N 0.000 description 1
- CKSXKXHNUKYIPW-UHFFFAOYSA-N CCC(CN(C)CC)(F)F Chemical compound CCC(CN(C)CC)(F)F CKSXKXHNUKYIPW-UHFFFAOYSA-N 0.000 description 1
- WGBBUURBHXLGFM-ZCFIWIBFSA-N CCCC[C@@H](C)N Chemical compound CCCC[C@@H](C)N WGBBUURBHXLGFM-ZCFIWIBFSA-N 0.000 description 1
- QAJHZTALENWKBV-UHFFFAOYSA-N CCCS(CNC)(=O)=O Chemical compound CCCS(CNC)(=O)=O QAJHZTALENWKBV-UHFFFAOYSA-N 0.000 description 1
- UBUONYTUWUVYLJ-UHFFFAOYSA-N CCOC(C(CC1)(CCC1=O)C#N)=O Chemical compound CCOC(C(CC1)(CCC1=O)C#N)=O UBUONYTUWUVYLJ-UHFFFAOYSA-N 0.000 description 1
- SQNJECPMDDKNOI-UHFFFAOYSA-N CCOCC(OC1)OCC1O Chemical compound CCOCC(OC1)OCC1O SQNJECPMDDKNOI-UHFFFAOYSA-N 0.000 description 1
- BIKULLBDZQBSQL-UHFFFAOYSA-N CN(c1c(CO2)ccc(Cl)c1)C2=O Chemical compound CN(c1c(CO2)ccc(Cl)c1)C2=O BIKULLBDZQBSQL-UHFFFAOYSA-N 0.000 description 1
- KDTVWEHAAISPNW-UHFFFAOYSA-N CN1CCSCC1 Chemical compound CN1CCSCC1 KDTVWEHAAISPNW-UHFFFAOYSA-N 0.000 description 1
- QQHKORBYPRQHHB-UHFFFAOYSA-N COC(C(CC1)CC=C1O)=O Chemical compound COC(C(CC1)CC=C1O)=O QQHKORBYPRQHHB-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class
- C07J53/002—Carbocyclic rings fused
-
- 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
-
- 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Virology (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261599040P | 2012-02-15 | 2012-02-15 | |
| US61/599,040 | 2012-02-15 | ||
| US13/760,726 | 2013-02-06 | ||
| US13/760,726 US8906889B2 (en) | 2012-02-15 | 2013-02-06 | C-3 cycloalkenyl triterpenoids with HIV maturation inhibitory activity |
| PCT/US2013/025897 WO2013123019A1 (en) | 2012-02-15 | 2013-02-13 | C-3 cycloalkenyl triterpenoids with hiv maturation inhibitory activity |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015510515A JP2015510515A (ja) | 2015-04-09 |
| JP2015510515A5 JP2015510515A5 (https=) | 2016-03-17 |
| JP6155285B2 true JP6155285B2 (ja) | 2017-06-28 |
Family
ID=48946098
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014557739A Expired - Fee Related JP6155285B2 (ja) | 2012-02-15 | 2013-02-13 | Ｈｉｖ成熟阻害活性のあるｃ−３シクロアルケニルトリテルペノイド |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US8906889B2 (https=) |
| EP (1) | EP2814834B1 (https=) |
| JP (1) | JP6155285B2 (https=) |
| KR (1) | KR20140123584A (https=) |
| CN (2) | CN106046106A (https=) |
| AR (1) | AR089996A1 (https=) |
| AU (1) | AU2013221725B2 (https=) |
| BR (1) | BR112014019672A8 (https=) |
| CA (1) | CA2864656A1 (https=) |
| CL (1) | CL2014002141A1 (https=) |
| CO (1) | CO7061077A2 (https=) |
| EA (1) | EA024361B1 (https=) |
| ES (1) | ES2656984T3 (https=) |
| HK (1) | HK1204608A1 (https=) |
| IL (1) | IL234077A (https=) |
| MX (1) | MX2014009235A (https=) |
| MY (1) | MY166793A (https=) |
| NZ (1) | NZ631408A (https=) |
| PE (1) | PE20142315A1 (https=) |
| PH (1) | PH12014501816A1 (https=) |
| PT (1) | PT2814834T (https=) |
| SG (1) | SG11201404748XA (https=) |
| TW (1) | TW201336863A (https=) |
| UY (1) | UY34627A (https=) |
| WO (1) | WO2013123019A1 (https=) |
| ZA (1) | ZA201406724B (https=) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8889854B2 (en) | 2012-05-07 | 2014-11-18 | Bristol-Myers Squibb Company | C-17 bicyclic amines of triterpenoids with HIV maturation inhibitory activity |
| SG11201505639SA (en) | 2013-02-06 | 2015-08-28 | Bristol Myers Squibb Co | C-19 modified triterpenoids with hiv maturation inhibitory activity |
| SI3129392T1 (sl) * | 2014-04-11 | 2020-11-30 | VIIV Healthcare UK(No.4) Limited | Triterpenoidi z inhibitorno aktivnostjo maturacije HIV-a, substituirani na položaju 3 z nearomatskim obročem, ki nosi haloalkilni substituent |
| WO2015195776A1 (en) | 2014-06-19 | 2015-12-23 | Bristol-Myers Squibb Company | Betulinic acid derivatives with hiv maturation inhibitory activity |
| EP3218388A1 (en) | 2014-11-14 | 2017-09-20 | VIIV Healthcare UK (No.5) Limited | C17-aryl substituted betulinic acid analogs |
| KR20170092580A (ko) * | 2014-11-14 | 2017-08-11 | 비브 헬스케어 유케이 (넘버5) 리미티드 | 연장된 베툴린산 유사체 |
| CN107250153A (zh) * | 2014-11-14 | 2017-10-13 | Viiv保健英国第五有限公司 | 氧代羽扇豆烯衍生物 |
| RU2017134461A (ru) * | 2015-04-14 | 2019-05-14 | ВАЙВ ХЕЛТКЕР ЮКей (N4) ЛИМИТЕД | Способы получения ингибитора созревания HIV |
| RU2018105352A (ru) | 2015-07-28 | 2019-08-29 | ГлаксоСмитКлайн Интеллекчуал Проперти (N2) Лимитед | Производные бетулина для предупреждения или лечения ВИЧ-инфекций |
| WO2017017609A1 (en) | 2015-07-28 | 2017-02-02 | Glaxosmithkline Intellectual Property (No.2) Limited | Betuin derivatives for preventing or treating hiv infections |
| RU2018112958A (ru) | 2015-09-24 | 2019-10-28 | ГлаксоСмитКлайн Интеллекчуал Проперти (N2) Лимитед | Соединения с ингибирующей созревание ВИЧ активностью |
| WO2017125870A1 (en) * | 2016-01-20 | 2017-07-27 | Glaxosmithkline Intellectual Property (No.2) Limited | Amine derivatives of lupanes with hiv maturation inhibitory activity |
| AR107512A1 (es) * | 2016-02-04 | 2018-05-09 | VIIV HEALTHCARE UK Nº 5 LTD | Triterpenoides modificados en c-3 y c-17 como inhibidores del vih-1 |
| CN106905264B (zh) * | 2017-04-12 | 2019-06-07 | 连云港杰瑞药业有限公司 | 一种合成阿扎拉韦中间体的方法 |
| WO2019055280A1 (en) | 2017-09-13 | 2019-03-21 | Emmyon, Inc. | DIETHANOLAMINE SALTS AND URSOLIC ACID MORPHOLIN |
| ES2970042T3 (es) | 2018-04-24 | 2024-05-24 | Viiv Healthcare Uk No 5 Ltd | Compuestos con actividad inhibidora de la maduración del VIH |
| CN109705189B (zh) * | 2018-12-29 | 2020-06-05 | 中国医学科学院药用植物研究所 | 具有式i所示结构的三萜衍生物及其制备方法和应用 |
| SI3924361T1 (sl) | 2019-02-11 | 2024-02-29 | Hetero Labs Limited | Novi derivati triterpena kot zaviralci virusa hiv |
| WO2020229398A1 (de) | 2019-05-14 | 2020-11-19 | Bayer Aktiengesellschaft | (1-alkenyl)-substituierte pyrazole und triazole als schädlingsbekämpfungsmittel |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5413999A (en) | 1991-11-08 | 1995-05-09 | Merck & Co., Inc. | HIV protease inhibitors useful for the treatment of AIDS |
| US5962527A (en) | 1995-03-21 | 1999-10-05 | The Board Of Trustees Of The University Of Illinois | Method and composition for treating cancers |
| US5869535A (en) | 1995-03-21 | 1999-02-09 | The Board Of Trustees Of The University Of Illinois | Method and composition for selectively inhibiting melanoma |
| US5679828A (en) | 1995-06-05 | 1997-10-21 | Biotech Research Labs, Inc. | Betulinic acid and dihydrobetulinic acid derivatives and uses therefor |
| US20040110785A1 (en) | 2001-02-02 | 2004-06-10 | Tao Wang | Composition and antiviral activity of substituted azaindoleoxoacetic piperazine derivatives |
| US7365221B2 (en) | 2002-09-26 | 2008-04-29 | Panacos Pharmaceuticals, Inc. | Monoacylated betulin and dihydrobetulin derivatives, preparation thereof and use thereof |
| US20050014730A1 (en) | 2003-04-02 | 2005-01-20 | Carlson Robert M. | Anti-fungal formulation of triterpene and essential oil |
| US7745625B2 (en) | 2004-03-15 | 2010-06-29 | Bristol-Myers Squibb Company | Prodrugs of piperazine and substituted piperidine antiviral agents |
| EP1730163A4 (en) | 2004-03-17 | 2009-12-30 | Panacos Pharmaceuticals Inc | Pharmaceutical salts of 3-O- (3,3-dimethylsuccinyl) betulinic acid |
| TW200628161A (en) | 2004-11-12 | 2006-08-16 | Panacos Pharmaceuticals Inc | Novel betulin derivatives, preparation thereof and use thereof |
| WO2008127364A2 (en) | 2006-10-13 | 2008-10-23 | Myriad Genetics, Inc. | Antiviral compounds and use thereof |
| WO2008115281A2 (en) | 2006-10-16 | 2008-09-25 | Myriad Genetics, Inc. | Compounds for treating viral infections |
| US20090062243A1 (en) | 2007-08-03 | 2009-03-05 | Advanced Life Sciences, Inc. | Lupane-Type Triterpenoids Modified at 30-Position and Analogues Thereof |
| CN101981047A (zh) * | 2008-01-03 | 2011-02-23 | Viro化学制药公司 | 新的羽扇烷衍生物 |
| CA2714049A1 (en) | 2008-02-14 | 2009-08-20 | Virochem Pharma Inc. | Novel 17.beta. lupane derivatives |
| US9067966B2 (en) | 2009-07-14 | 2015-06-30 | Hetero Research Foundation, Hetero Drugs Ltd. | Lupeol-type triterpene derivatives as antivirals |
| WO2011075517A1 (en) | 2009-12-17 | 2011-06-23 | Merck Sharp & Dohme Corp. | Aminopyrimidines as syk inhibitors |
| US8802661B2 (en) | 2010-06-04 | 2014-08-12 | Bristol-Myers Squibb Company | C-28 amides of modified C-3 betulinic acid derivatives as HIV maturation inhibitors |
| CN103038245B (zh) | 2010-06-04 | 2015-03-25 | 百时美施贵宝公司 | 作为hiv成熟抑制剂的c-3经修饰的桦木酸衍生物 |
| AP2013006706A0 (en) | 2010-07-02 | 2013-02-28 | Gilead Sciences Inc | Napht-2-ylacetic acid derivatives to treat AIDS |
| PL2670764T3 (pl) * | 2011-01-31 | 2016-02-29 | Bristol Myers Squibb Co | C-28 aminy zmodyfikowanych C-3 pochodnych kwasu betulinowego jako inhibitory dojrzewania HIV |
| KR101886467B1 (ko) * | 2011-01-31 | 2018-08-07 | 비브 헬스케어 유케이 (넘버4) 리미티드 | Hiv 성숙 억제 활성을 갖는 c-17 및 c-3 변형 트리테르페노이드 |
| WO2013043778A1 (en) | 2011-09-21 | 2013-03-28 | Bristol-Myers Squibb Company | Novel betulinic acid derivatives with antiviral activity |
| US8889854B2 (en) | 2012-05-07 | 2014-11-18 | Bristol-Myers Squibb Company | C-17 bicyclic amines of triterpenoids with HIV maturation inhibitory activity |
| SG11201505639SA (en) * | 2013-02-06 | 2015-08-28 | Bristol Myers Squibb Co | C-19 modified triterpenoids with hiv maturation inhibitory activity |
-
2013
- 2013-02-06 US US13/760,726 patent/US8906889B2/en active Active
- 2013-02-08 TW TW102105203A patent/TW201336863A/zh unknown
- 2013-02-13 CA CA2864656A patent/CA2864656A1/en not_active Abandoned
- 2013-02-13 WO PCT/US2013/025897 patent/WO2013123019A1/en not_active Ceased
- 2013-02-13 NZ NZ631408A patent/NZ631408A/en not_active IP Right Cessation
- 2013-02-13 PT PT137074936T patent/PT2814834T/pt unknown
- 2013-02-13 HK HK15105069.8A patent/HK1204608A1/xx unknown
- 2013-02-13 PE PE2014001279A patent/PE20142315A1/es not_active Application Discontinuation
- 2013-02-13 MX MX2014009235A patent/MX2014009235A/es unknown
- 2013-02-13 SG SG11201404748XA patent/SG11201404748XA/en unknown
- 2013-02-13 MY MYPI2014702277A patent/MY166793A/en unknown
- 2013-02-13 ES ES13707493.6T patent/ES2656984T3/es active Active
- 2013-02-13 CN CN201610397768.6A patent/CN106046106A/zh active Pending
- 2013-02-13 EP EP13707493.6A patent/EP2814834B1/en active Active
- 2013-02-13 CN CN201380019696.6A patent/CN104220451B/zh not_active Expired - Fee Related
- 2013-02-13 BR BR112014019672A patent/BR112014019672A8/pt not_active Application Discontinuation
- 2013-02-13 JP JP2014557739A patent/JP6155285B2/ja not_active Expired - Fee Related
- 2013-02-13 KR KR1020147025339A patent/KR20140123584A/ko not_active Ceased
- 2013-02-13 AU AU2013221725A patent/AU2013221725B2/en not_active Ceased
- 2013-02-13 EA EA201491531A patent/EA024361B1/ru not_active IP Right Cessation
- 2013-02-14 AR ARP130100466A patent/AR089996A1/es unknown
- 2013-02-14 UY UY0001034627A patent/UY34627A/es not_active Application Discontinuation
-
2014
- 2014-08-12 PH PH12014501816A patent/PH12014501816A1/en unknown
- 2014-08-12 IL IL234077A patent/IL234077A/en not_active IP Right Cessation
- 2014-08-13 CL CL2014002141A patent/CL2014002141A1/es unknown
- 2014-08-28 CO CO14189685A patent/CO7061077A2/es unknown
- 2014-09-12 ZA ZA2014/06724A patent/ZA201406724B/en unknown
Also Published As
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| JP6155285B2 (ja) | Ｈｉｖ成熟阻害活性のあるｃ−３シクロアルケニルトリテルペノイド | |
| JP6186012B2 (ja) | Ｃ−３アルキルおよびアルケニル修飾ベツリン酸誘導体 | |
| CA2801491C (en) | C-28 amides of modified c-3 betulinic acid derivatives as hiv maturation inhibitors | |
| JP6212545B2 (ja) | Ｈｉｖ成熟阻害活性を有するｃ−１７二環式アミンのトリテルペノイド | |
| US11464790B2 (en) | Triterpenoids with HIV maturation inhibitory activity | |
| HK40041853A (en) | Triterpenoids with hiv maturation inhibitory activity | |
| HK1232548B (en) | Triterpenoids with hiv maturation inhibitory activity, substituted in position 3 by a non-aromatic ring carrying a haloalkyl substituent |
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