TWI258481B - Hexacyclic compounds - Google Patents
Hexacyclic compounds Download PDFInfo
- Publication number
- TWI258481B TWI258481B TW091134463A TW91134463A TWI258481B TW I258481 B TWI258481 B TW I258481B TW 091134463 A TW091134463 A TW 091134463A TW 91134463 A TW91134463 A TW 91134463A TW I258481 B TWI258481 B TW I258481B
- Authority
- TW
- Taiwan
- Prior art keywords
- ethyl
- hydroxy
- pyrano
- quinazoline
- pyrido
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract description 35
- 150000003839 salts Chemical class 0.000 abstract description 8
- 230000002062 proliferating effect Effects 0.000 abstract description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 53
- -1 1-decylethyl Chemical group 0.000 description 31
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 26
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 18
- 229910052739 hydrogen Inorganic materials 0.000 description 11
- 239000001257 hydrogen Substances 0.000 description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 239000002585 base Substances 0.000 description 6
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 239000008194 pharmaceutical composition Substances 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 4
- 229910052717 sulfur Chemical group 0.000 description 4
- 239000011593 sulfur Chemical group 0.000 description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 3
- WNWVKZTYMQWFHE-UHFFFAOYSA-N 4-ethylmorpholine Chemical group [CH2]CN1CCOCC1 WNWVKZTYMQWFHE-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000003282 alkyl amino group Chemical group 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 238000003971 tillage Methods 0.000 description 3
- 125000006715 (C1-C5) alkylthio group Chemical group 0.000 description 2
- VOYADQIFGGIKAT-UHFFFAOYSA-N 1,3-dibutyl-4-hydroxy-2,6-dioxopyrimidine-5-carboximidamide Chemical compound CCCCn1c(O)c(C(N)=N)c(=O)n(CCCC)c1=O VOYADQIFGGIKAT-UHFFFAOYSA-N 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 229960005181 morphine Drugs 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- ZKXGQPQAMRSBOL-UHFFFAOYSA-N 1,2,3-trifluoro-9h-fluorene Chemical compound C12=CC=CC=C2CC2=C1C=C(F)C(F)=C2F ZKXGQPQAMRSBOL-UHFFFAOYSA-N 0.000 description 1
- VYXMUKDKNHUTAO-UHFFFAOYSA-N 1-[decyl(hydrazinyl)amino]decane Chemical group C(CCCCCCCCC)N(CCCCCCCCCC)NN VYXMUKDKNHUTAO-UHFFFAOYSA-N 0.000 description 1
- JRJOFXHBAVGTEW-UHFFFAOYSA-N 2,4,8-triazatricyclo[7.3.1.05,13]trideca-1(12),3,5(13),6,8,10-hexaene Chemical compound N1C=NC2=C3C(C=CC=C13)=NC=C2 JRJOFXHBAVGTEW-UHFFFAOYSA-N 0.000 description 1
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- 206010005003 Bladder cancer Diseases 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- 206010008342 Cervix carcinoma Diseases 0.000 description 1
- 206010009944 Colon cancer Diseases 0.000 description 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 description 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
- 208000005718 Stomach Neoplasms Diseases 0.000 description 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 description 1
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 201000010881 cervical cancer Diseases 0.000 description 1
- DOZZESQBLWOEBQ-UHFFFAOYSA-N chlorohydrazine Chemical compound NNCl DOZZESQBLWOEBQ-UHFFFAOYSA-N 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 206010017758 gastric cancer Diseases 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 201000005202 lung cancer Diseases 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical group NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- RONWGALEIBILOG-VMJVVOMYSA-N quinine sulfate Chemical compound [H+].[H+].[O-]S([O-])(=O)=O.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 RONWGALEIBILOG-VMJVVOMYSA-N 0.000 description 1
- 201000011549 stomach cancer Diseases 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 201000005112 urinary bladder cancer Diseases 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01128361 | 2001-11-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200408642A TW200408642A (en) | 2004-06-01 |
| TWI258481B true TWI258481B (en) | 2006-07-21 |
Family
ID=8179394
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW091134463A TWI258481B (en) | 2001-11-30 | 2002-11-27 | Hexacyclic compounds |
Country Status (28)
| Country | Link |
|---|---|
| US (2) | US6825194B2 (OSRAM) |
| EP (1) | EP1480984B9 (OSRAM) |
| JP (1) | JP4305909B2 (OSRAM) |
| KR (1) | KR100895746B1 (OSRAM) |
| CN (1) | CN100338066C (OSRAM) |
| AT (1) | ATE398131T1 (OSRAM) |
| AU (1) | AU2002356720B2 (OSRAM) |
| BR (1) | BR0214615A (OSRAM) |
| CA (1) | CA2468824C (OSRAM) |
| DE (1) | DE60227113D1 (OSRAM) |
| ES (1) | ES2307830T3 (OSRAM) |
| GT (1) | GT200200250A (OSRAM) |
| HU (1) | HUP0500062A3 (OSRAM) |
| IL (1) | IL162058A0 (OSRAM) |
| MX (1) | MXPA04005185A (OSRAM) |
| MY (1) | MY136138A (OSRAM) |
| NO (1) | NO329005B1 (OSRAM) |
| NZ (1) | NZ533568A (OSRAM) |
| PA (1) | PA8558901A1 (OSRAM) |
| PE (1) | PE20030725A1 (OSRAM) |
| PL (1) | PL207510B1 (OSRAM) |
| RS (1) | RS51051B (OSRAM) |
| RU (1) | RU2299212C2 (OSRAM) |
| TW (1) | TWI258481B (OSRAM) |
| UA (1) | UA80409C2 (OSRAM) |
| UY (1) | UY27560A1 (OSRAM) |
| WO (1) | WO2003045952A2 (OSRAM) |
| ZA (1) | ZA200404522B (OSRAM) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1777611A (zh) * | 2003-02-21 | 2006-05-24 | 中外制药株式会社 | 制备六环喜树碱衍生物的方法 |
| MXPA06011679A (es) | 2004-04-09 | 2007-01-23 | Chugai Pharmaceutical Co Ltd | Novedosos profarmacos solubles en agua. |
| TW200744603A (en) * | 2005-08-22 | 2007-12-16 | Chugai Pharmaceutical Co Ltd | Novel anticancer concomitant drug |
| US20090118271A1 (en) * | 2005-10-19 | 2009-05-07 | Chugai Seiyaku Kabushiki Kaisha | Preventive or Therapeutic Agents for Pancreatic Cancer, Ovarian Cancer, or Liver Cancer Comprising a Novel Water-Soluble Prodrug |
| RU2439073C1 (ru) * | 2010-07-13 | 2012-01-10 | Государственное образовательное учреждение высшего профессионального образования "Кубанский государственный технологический университет" (ГОУ ВПО "КубГТУ") | СПОСОБ ПОЛУЧЕНИЯ ПРОИЗВОДНЫХ ИНДОЛИЗИНО[7,6-b]ИНДОЛА |
| EP3946464B1 (en) | 2019-03-29 | 2022-08-31 | MedImmune Limited | Compounds and conjugates thereof |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4473692A (en) | 1981-09-04 | 1984-09-25 | Kabushiki Kaisha Yakult Honsha | Camptothecin derivatives and process for preparing same |
| US4939255A (en) * | 1987-06-24 | 1990-07-03 | Daiichi Pharmaceutical Co., Ltd. | Hexa-cyclic camptothecin derivatives |
| HU213136B (en) * | 1990-08-14 | 1997-02-28 | Kyorin Seiyaku Kk | Process for producing fluoroethyl camptothecin derivatives and pharmaceutical compositions containing them |
| JP3008226B2 (ja) * | 1991-01-16 | 2000-02-14 | 第一製薬株式会社 | 六環性化合物 |
| JP3359955B2 (ja) * | 1992-07-16 | 2002-12-24 | 第一製薬株式会社 | 抗腫瘍剤 |
| GB9402934D0 (en) * | 1994-02-16 | 1994-04-06 | Erba Carlo Spa | Camptothecin derivatives and process for their preparation |
| US5663177A (en) * | 1995-05-31 | 1997-09-02 | Smithkline Beecham Corporation | Water soluble camptothecin analogs |
| WO1998035940A1 (en) | 1997-02-14 | 1998-08-20 | Bionumerik Pharmaceuticals, Inc. | Highly lipophilic camptothecin derivatives |
| GB9715821D0 (en) * | 1997-07-25 | 1997-10-01 | Pharmacia & Upjohn Spa | Amidino-camptothecin derivatives |
-
2002
- 2002-11-25 AU AU2002356720A patent/AU2002356720B2/en not_active Ceased
- 2002-11-25 ES ES02803790T patent/ES2307830T3/es not_active Expired - Lifetime
- 2002-11-25 DE DE60227113T patent/DE60227113D1/de not_active Expired - Lifetime
- 2002-11-25 MX MXPA04005185A patent/MXPA04005185A/es active IP Right Grant
- 2002-11-25 CA CA2468824A patent/CA2468824C/en not_active Expired - Fee Related
- 2002-11-25 BR BR0214615-0A patent/BR0214615A/pt not_active IP Right Cessation
- 2002-11-25 IL IL16205802A patent/IL162058A0/xx not_active IP Right Cessation
- 2002-11-25 RS YUP-470/04A patent/RS51051B/sr unknown
- 2002-11-25 UA UA20040605013A patent/UA80409C2/uk unknown
- 2002-11-25 NZ NZ533568A patent/NZ533568A/en not_active IP Right Cessation
- 2002-11-25 JP JP2003547402A patent/JP4305909B2/ja not_active Expired - Fee Related
- 2002-11-25 PL PL370479A patent/PL207510B1/pl not_active IP Right Cessation
- 2002-11-25 EP EP02803790A patent/EP1480984B9/en not_active Expired - Lifetime
- 2002-11-25 WO PCT/EP2002/013216 patent/WO2003045952A2/en not_active Ceased
- 2002-11-25 HU HU0500062A patent/HUP0500062A3/hu unknown
- 2002-11-25 CN CNB028277465A patent/CN100338066C/zh not_active Expired - Fee Related
- 2002-11-25 AT AT02803790T patent/ATE398131T1/de not_active IP Right Cessation
- 2002-11-25 RU RU2004119841/04A patent/RU2299212C2/ru not_active IP Right Cessation
- 2002-11-25 KR KR1020047008223A patent/KR100895746B1/ko not_active Expired - Fee Related
- 2002-11-26 US US10/304,672 patent/US6825194B2/en not_active Expired - Fee Related
- 2002-11-27 TW TW091134463A patent/TWI258481B/zh not_active IP Right Cessation
- 2002-11-28 PE PE2002001148A patent/PE20030725A1/es not_active Application Discontinuation
- 2002-11-28 PA PA20028558901A patent/PA8558901A1/es unknown
- 2002-11-28 MY MYPI20024479A patent/MY136138A/en unknown
- 2002-11-29 GT GT200200250A patent/GT200200250A/es unknown
- 2002-11-29 UY UY27560A patent/UY27560A1/es not_active Application Discontinuation
-
2004
- 2004-06-08 ZA ZA200404522A patent/ZA200404522B/en unknown
- 2004-06-29 NO NO20042729A patent/NO329005B1/no not_active IP Right Cessation
- 2004-09-16 US US10/942,044 patent/US7109195B2/en not_active Expired - Fee Related
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