KR840008156A - (1H-테트라졸-5-일)테트라졸로[1,5-a]-퀴놀린의 제조방법 - Google Patents
(1H-테트라졸-5-일)테트라졸로[1,5-a]-퀴놀린의 제조방법 Download PDFInfo
- Publication number
- KR840008156A KR840008156A KR1019840001504A KR840001504A KR840008156A KR 840008156 A KR840008156 A KR 840008156A KR 1019840001504 A KR1019840001504 A KR 1019840001504A KR 840001504 A KR840001504 A KR 840001504A KR 840008156 A KR840008156 A KR 840008156A
- Authority
- KR
- South Korea
- Prior art keywords
- reacted
- tetrazolo
- ammonium chloride
- inert solvent
- sodium azide
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 8
- LIRHINFDFZWXPL-UHFFFAOYSA-N 4-(2h-tetrazol-5-yl)tetrazolo[1,5-a]quinoline Chemical compound C=1C=CC=C(N2N=NN=C22)C=1C=C2C=1N=NNN=1 LIRHINFDFZWXPL-UHFFFAOYSA-N 0.000 title claims 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims 20
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims 20
- -1 methylenedioxy Chemical group 0.000 claims 12
- 235000019270 ammonium chloride Nutrition 0.000 claims 10
- 239000012442 inert solvent Substances 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 7
- 150000001875 compounds Chemical class 0.000 claims 6
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 4
- 229910052794 bromium Inorganic materials 0.000 claims 4
- 229910052801 chlorine Inorganic materials 0.000 claims 4
- 239000000460 chlorine Substances 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 150000002431 hydrogen Chemical group 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- HHFCAUSIBNOUOP-UHFFFAOYSA-N tetrazolo[1,5-a]quinoline Chemical compound C1=CC2=NN=NN2C2=CC=CC=C21 HHFCAUSIBNOUOP-UHFFFAOYSA-N 0.000 claims 2
- 231100000331 toxic Toxicity 0.000 claims 2
- 230000002588 toxic effect Effects 0.000 claims 2
- FMQOMPVZLLUVOD-UHFFFAOYSA-N 1-chloroisoquinoline-4-carbonitrile Chemical compound C1=CC=C2C(Cl)=NC=C(C#N)C2=C1 FMQOMPVZLLUVOD-UHFFFAOYSA-N 0.000 claims 1
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Chemical compound C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 claims 1
- WBJXNFJBFBJGHO-UHFFFAOYSA-N 2-bromoquinoline-4-carbonitrile Chemical compound C1=CC=CC2=NC(Br)=CC(C#N)=C21 WBJXNFJBFBJGHO-UHFFFAOYSA-N 0.000 claims 1
- GETLLXMNDLMIJO-UHFFFAOYSA-N 2-chloro-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound N#CC1=C(Cl)N=C2C=C(OC)C(OC)=CC2=C1 GETLLXMNDLMIJO-UHFFFAOYSA-N 0.000 claims 1
- RWTVCAFOPUIWIV-UHFFFAOYSA-N 2-chloro-6,7-dimethylquinoline-3-carbonitrile Chemical compound N#CC1=C(Cl)N=C2C=C(C)C(C)=CC2=C1 RWTVCAFOPUIWIV-UHFFFAOYSA-N 0.000 claims 1
- UGTRDMPALMEDBU-UHFFFAOYSA-N 2-chloroquinoline-3-carbonitrile Chemical compound C1=CC=C2C=C(C#N)C(Cl)=NC2=C1 UGTRDMPALMEDBU-UHFFFAOYSA-N 0.000 claims 1
- NDNPEMVQUZNWPO-UHFFFAOYSA-N 7,8-dimethoxy-4-(2h-tetrazol-5-yl)tetrazolo[1,5-a]quinoline Chemical compound C12=NN=NN2C=2C=C(OC)C(OC)=CC=2C=C1C1=NN=NN1 NDNPEMVQUZNWPO-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/18—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/36—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Luminescent Compositions (AREA)
Abstract
내용 없음.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (10)
- 일반식(II)의 할로시아노 화합물을 불활성 용매 중에서 나트륨 아지드 및 염화 암모늄과 반응시킨 다음, 염을 원하는 경우에는 임의로 적합한 염기와 반응시킴을 특징으로 하여 일반식(I)의 화합물 및 약제학적으로 무독한 그의 염을 제조하는 방법.상기식에서, Tet는 환 시스템에 결합되어 이성체 형태를 나타내는 구조식의 2가 테트라졸로 그룹이고, A는 -CH=또는 -N=이며, n은 0,1 또는 2이고, x는 수소, C1내지 C4의 알킬, C1내지 C4의 알콕시, 할로겐, 메틸어캅토 또는 메틸설포닐이거나 2개의 x가 결합하여 메틸렌디옥시를 나타낼 수 있는데, 단, x가 메틸머캅토 또는 메틸설포닐일 경우에는 n은 1이어야 하며, 일반식(II)화합물에서, -CN은 4- 또는 5-위치에 결합되고, Z는 -N=C(Hal)- (여기서 Hal은 염소 또는 브롬이다)이다.
- 제1항에 있어서, 다음 일반식(III)의 할로시아노 화합물을 불활성 용매 중에서 나트륨아지드 및 염화암모늄과 반응시킴을 특징으로 하여 일반식(Ia)의 화합물 및 약제학적으로 무독한 그의 염을 제조하는 방법.상기식에서, n은 0,1 또는 2이고, x는 수소, C1내지 C4의 알킬, C1내지 C4의 알콕시, 할로겐, 메틸머캅토 또는 메틸설포닐이거나 2개의 x가 결합하여 메틸렌디옥시를 나타낼 수 있는데, 단, x가 메틸머캅토 또는 메틸설포닐일 경우에는 n은 1이어야 하며, 일반식(III)에서, -CN은 4- 또는 5- 위치에 결합되고, Hal은 염소 또는 브롬이다.
- 제1항에 있어서, 다음 일반식(II)의 할로시아노 화합물을 불활성 용매 중에서 나트륨아지드 및 염화암모늄과 반응시킴을 특징으로 하여 일반식(Ib)의 화합물 및 약제학적으로 무독한 이의 염을 제조하는 방법.상기식에서, n은 0,1 또는 2이고, x는 수소, C1내지 C4의 알킬, C1내지 C4의 알콕시, 할로겐, 메틸머캅토, 또는 메틸설포닐이거나 2개의 x가 결합하여 메틸렌디옥시를 나타낼 수 있는데, 단, x가 메틸머캅토 또는 메틸설포닐일 경우에는 n은 1이어야 하며, Hal은 염소 또는 브롬이다.
- 제1항에 있어서, 2-Hal-3-시아노퀴놀린(여기서 Hal은 염소 또는 브롬이다)을 불활성 용매 중에서 나트륨 아지드 및 염화암모늄과 반응시킴을 특징으로 하여 -4(1H-테트라졸-5-일)테트라졸로[1,5-a]퀴놀린을 제조하는 방법.
- 제1항에 있어서, -클로로-3-시아노퀴놀린을 불활성 용매 중에서 나트륨아지드 및 염화 암모늄과 반응시킴을 특징으로 하여 4-(1H-테트라졸-5-일)테트라졸로[1,5-a]-퀴놀린을 제조하는 방법.
- 제1항에 있어서, 2-클로로-3-시아노퀴놀린을 불활성 용매 중에서 나트륨아지드 및 염화 암모늄과 반응시켜 4-(1H-테트라졸-5-일)테트라졸로[1,5-a]퀴놀린을 수득한 다음 N-메틸-D-글루카민과 반응시켜 목적하는 염을 생성시킴을 특징으로 하여 4-(1H-테트라졸-5-일)테트라졸로 [1,5-a]퀴놀린의 N-메틸글루카민과 염을 제조하는 방법.
- 제1항에 있어서, 2-클로로-3-시아노-6,7-디메틸퀴놀린을 불활성용매 중에서 나트륨 아지드 및 염화암모늄과 반응시킴을 특징으로 하여 7,8-디메틸-4(1H-테트라졸-5-일)테트라졸로[1,5-a]퀴놀린을 제조하는 방법.
- 제1항에 있어서, 2-클로로-3-시아노-6,7-디메톡시퀴놀린을 불활성 용매 중에서 나트륨 아지드 및 염화 암모늄과 반응시킴을 특징으로 하여 7,8-디메톡시-4-(1H-테트라졸-5-일)테트라졸로[1,5-a]퀴놀린을 제조하는 방법.
- 제1항에 있어서, 2-브로모-4-시아노퀴놀린을 불활성 용매 중에서 나트륨 아지드 및 염화 암모늄과 반응시킴을 특징으로 하여 5-(1H-테트라졸-5-일)테트라졸로[1,5-a]퀴놀린을 제조하는 방법.
- 제1항에 있어서, 1-클로로-4-시아노이소퀴놀린을 불활성 용매 중에서 나트륨아지드 및 염화암모늄과 반응시킴을 특징으로 하여 5-(1H-테트라졸-5-일)테트라졸로[5,1-a]-이소퀴놀린을 제조하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/478,964 US4496569A (en) | 1983-03-25 | 1983-03-25 | Antiallergic (1H-tetrazol-5-yl)tetrazolo[1,5-a]quinolines and derivatives thereof |
| US478964 | 1983-03-25 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR840008156A true KR840008156A (ko) | 1984-12-13 |
| KR900003649B1 KR900003649B1 (ko) | 1990-05-28 |
Family
ID=23902115
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019840001504A KR900003649B1 (ko) | 1983-03-25 | 1984-03-23 | (1H-테트라졸-5-일)테트라졸로[1,5-a]-퀴놀린의 제조방법 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4496569A (ko) |
| EP (1) | EP0120484B1 (ko) |
| JP (1) | JPS59176287A (ko) |
| KR (1) | KR900003649B1 (ko) |
| AT (1) | ATE26717T1 (ko) |
| AU (1) | AU558762B2 (ko) |
| CA (1) | CA1252100A (ko) |
| DE (1) | DE3463271D1 (ko) |
| DK (1) | DK165694C (ko) |
| ES (1) | ES8601970A1 (ko) |
| GR (1) | GR81463B (ko) |
| IE (1) | IE57072B1 (ko) |
| IL (1) | IL71318A (ko) |
| MX (1) | MX9203341A (ko) |
| NO (1) | NO161067C (ko) |
| NZ (1) | NZ207582A (ko) |
| PH (1) | PH20353A (ko) |
| PT (1) | PT78288B (ko) |
| ZA (1) | ZA842067B (ko) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4014171A1 (de) * | 1990-05-03 | 1991-11-07 | Basf Ag | Cyanochinolinverbindungen |
| CA2184694A1 (en) * | 1994-03-25 | 1995-10-05 | Kay K. Olmstead | Process for preparing (1h-tetrazol-5-yl)tetrazolo [1,5-a] quinolines andnaphthyridines |
| JP3674407B2 (ja) | 1999-09-21 | 2005-07-20 | ヤマハ株式会社 | 演奏データ編集装置、方法及び記録媒体 |
| US7358259B2 (en) | 2003-09-26 | 2008-04-15 | Rigel Pharmaceuticals, Inc. | HCV inhibitors and methods of using them |
| WO2005121138A2 (en) * | 2004-06-03 | 2005-12-22 | Rigel Pharmaceuticals, Inc. | Heterotricyclic compounds for use as hcv inhibitors |
| KR101101950B1 (ko) * | 2011-11-04 | 2012-01-02 | 이동진 | 왕복 페달식 자전거 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3764681A (en) * | 1970-07-08 | 1973-10-09 | Lilly Co Eli | Certain tetrazolo-(1,5-a) quinoline compounds as fungus control agents |
| US4035368A (en) * | 1975-04-02 | 1977-07-12 | Riker Laboratories, Inc. | Substituted 3-(1H-tetrazol-5-yl)-quinoline compounds |
-
1983
- 1983-03-25 US US06/478,964 patent/US4496569A/en not_active Expired - Lifetime
-
1984
- 1984-03-20 ZA ZA842067A patent/ZA842067B/xx unknown
- 1984-03-20 CA CA000449960A patent/CA1252100A/en not_active Expired
- 1984-03-21 PT PT78288A patent/PT78288B/pt not_active IP Right Cessation
- 1984-03-21 AU AU25953/84A patent/AU558762B2/en not_active Ceased
- 1984-03-21 GR GR74165A patent/GR81463B/el unknown
- 1984-03-21 NZ NZ207582A patent/NZ207582A/en unknown
- 1984-03-22 IL IL71318A patent/IL71318A/xx not_active IP Right Cessation
- 1984-03-22 JP JP59053690A patent/JPS59176287A/ja active Granted
- 1984-03-22 ES ES530876A patent/ES8601970A1/es not_active Expired
- 1984-03-22 PH PH30426A patent/PH20353A/en unknown
- 1984-03-23 KR KR1019840001504A patent/KR900003649B1/ko not_active IP Right Cessation
- 1984-03-23 NO NO841156A patent/NO161067C/no unknown
- 1984-03-23 IE IE719/84A patent/IE57072B1/en not_active IP Right Cessation
- 1984-03-23 EP EP84103232A patent/EP0120484B1/en not_active Expired
- 1984-03-23 AT AT84103232T patent/ATE26717T1/de not_active IP Right Cessation
- 1984-03-23 DE DE8484103232T patent/DE3463271D1/de not_active Expired
- 1984-03-23 DK DK165584A patent/DK165694C/da not_active IP Right Cessation
-
1992
- 1992-06-25 MX MX9203341A patent/MX9203341A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL71318A0 (en) | 1984-06-29 |
| ATE26717T1 (de) | 1987-05-15 |
| AU558762B2 (en) | 1987-02-05 |
| DK165584A (da) | 1984-09-26 |
| ES530876A0 (es) | 1985-11-01 |
| IE57072B1 (en) | 1992-04-22 |
| ZA842067B (en) | 1984-10-31 |
| PH20353A (en) | 1986-12-04 |
| GR81463B (ko) | 1984-12-11 |
| DK165694B (da) | 1993-01-04 |
| NO161067C (no) | 1989-06-28 |
| PT78288B (en) | 1986-04-22 |
| IE840719L (en) | 1984-09-25 |
| PT78288A (en) | 1984-04-01 |
| MX9203341A (es) | 1992-08-01 |
| DK165584D0 (da) | 1984-03-23 |
| NZ207582A (en) | 1986-10-08 |
| CA1252100A (en) | 1989-04-04 |
| NO841156L (no) | 1984-09-26 |
| EP0120484B1 (en) | 1987-04-22 |
| EP0120484A1 (en) | 1984-10-03 |
| JPS59176287A (ja) | 1984-10-05 |
| JPH0415791B2 (ko) | 1992-03-19 |
| NO161067B (no) | 1989-03-20 |
| IL71318A (en) | 1986-11-30 |
| KR900003649B1 (ko) | 1990-05-28 |
| AU2595384A (en) | 1984-09-27 |
| ES8601970A1 (es) | 1985-11-01 |
| DE3463271D1 (en) | 1987-05-27 |
| DK165694C (da) | 1993-06-07 |
| US4496569A (en) | 1985-01-29 |
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