UA77737C2 - Benzothiazine and benzothiadizine derivatives, a process for preparation thereof and pharmaceutical composition containing them - Google Patents
Benzothiazine and benzothiadizine derivatives, a process for preparation thereof and pharmaceutical composition containing them Download PDFInfo
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- UA77737C2 UA77737C2 UA20040706011A UA20040706011A UA77737C2 UA 77737 C2 UA77737 C2 UA 77737C2 UA 20040706011 A UA20040706011 A UA 20040706011A UA 20040706011 A UA20040706011 A UA 20040706011A UA 77737 C2 UA77737 C2 UA 77737C2
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- 238000000034 method Methods 0.000 title claims description 34
- 238000002360 preparation method Methods 0.000 title claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 6
- 230000008569 process Effects 0.000 title description 5
- UJVBZCCNLAAMOV-UHFFFAOYSA-N 2h-1,2-benzothiazine Chemical compound C1=CC=C2C=CNSC2=C1 UJVBZCCNLAAMOV-UHFFFAOYSA-N 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 138
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 35
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 16
- 125000003118 aryl group Chemical group 0.000 claims abstract description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
- 150000002367 halogens Chemical group 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 5
- MGRVRXRGTBOSHW-UHFFFAOYSA-N (aminomethyl)phosphonic acid Chemical compound NCP(O)(O)=O MGRVRXRGTBOSHW-UHFFFAOYSA-N 0.000 claims abstract 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 33
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- 125000005843 halogen group Chemical group 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
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- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 8
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- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
- 125000002619 bicyclic group Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
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- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 4
- 239000012279 sodium borohydride Substances 0.000 claims description 4
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- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 3
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- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 claims description 3
- QLZHNIAADXEJJP-UHFFFAOYSA-L dioxido-oxo-phenyl-$l^{5}-phosphane Chemical compound [O-]P([O-])(=O)C1=CC=CC=C1 QLZHNIAADXEJJP-UHFFFAOYSA-L 0.000 claims description 3
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- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
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- 150000004681 metal hydrides Chemical class 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 150000002901 organomagnesium compounds Chemical class 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
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- 125000006239 protecting group Chemical group 0.000 claims description 2
- 230000008707 rearrangement Effects 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 241001206439 Motya Species 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 150000004678 hydrides Chemical class 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 238000002844 melting Methods 0.000 description 76
- 230000008018 melting Effects 0.000 description 76
- 238000004452 microanalysis Methods 0.000 description 66
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- HAVZTGSQJIEKPI-UHFFFAOYSA-N benzothiadiazine Chemical compound C1=CC=C2C=NNSC2=C1 HAVZTGSQJIEKPI-UHFFFAOYSA-N 0.000 description 22
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- QRKDOAWSBBGNLE-UHFFFAOYSA-N 2h-1,2,4-benzothiadiazine Chemical compound C1=CC=C2N=CNSC2=C1 QRKDOAWSBBGNLE-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/02—1,2-Thiazines; Hydrogenated 1,2-thiazines
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0116621A FR2833956B1 (fr) | 2001-12-21 | 2001-12-21 | Nouveaux derives de benzothiazine et de benzothiadiazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| PCT/FR2002/004485 WO2003053979A1 (fr) | 2001-12-21 | 2002-12-20 | Nouveaux derives de benzothiazine et benzothiadiazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA77737C2 true UA77737C2 (en) | 2007-01-15 |
Family
ID=8870809
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA20040706011A UA77737C2 (en) | 2001-12-21 | 2002-12-20 | Benzothiazine and benzothiadizine derivatives, a process for preparation thereof and pharmaceutical composition containing them |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US7253161B2 (fr) |
| EP (1) | EP1480986A1 (fr) |
| JP (1) | JP2005518386A (fr) |
| KR (1) | KR100586685B1 (fr) |
| CN (1) | CN1289509C (fr) |
| AR (1) | AR038028A1 (fr) |
| AU (1) | AU2002364674B2 (fr) |
| BR (1) | BR0214973A (fr) |
| CA (1) | CA2471263A1 (fr) |
| EA (1) | EA007227B1 (fr) |
| FR (1) | FR2833956B1 (fr) |
| GE (1) | GEP20063759B (fr) |
| HK (1) | HK1071749A1 (fr) |
| HU (1) | HUP0402585A3 (fr) |
| MA (1) | MA27090A1 (fr) |
| MX (1) | MXPA04005837A (fr) |
| NO (1) | NO20042978L (fr) |
| NZ (1) | NZ533328A (fr) |
| PL (1) | PL370159A1 (fr) |
| UA (1) | UA77737C2 (fr) |
| WO (1) | WO2003053979A1 (fr) |
| ZA (1) | ZA200404294B (fr) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2856065B1 (fr) * | 2003-06-13 | 2005-08-19 | Servier Lab | Nouveaux derives de benzothiazine et benzothiadiazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| FR2856064B1 (fr) * | 2003-06-13 | 2005-08-19 | Servier Lab | Nouveaux derives de benzothiazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| FR2877342B1 (fr) * | 2004-11-03 | 2007-01-26 | Servier Lab | Nouveaux derives de benzothiadiazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2877338B1 (fr) * | 2004-11-03 | 2007-01-26 | Servier Lab | Nouveaux derives de benzothiadiazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2879201B1 (fr) | 2004-12-10 | 2007-02-16 | Servier Lab | Nouveaux derives de benzothiazine et benzothiadiazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2955106B1 (fr) * | 2010-01-08 | 2011-12-23 | Servier Lab | Nouveaux derives de benzothiadiazines cyclopropylees, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| JP6134654B2 (ja) | 2012-02-08 | 2017-05-24 | 武田薬品工業株式会社 | 複素環化合物およびその用途 |
| US11447488B2 (en) | 2017-10-06 | 2022-09-20 | Takeda Pharmaceutical Company Limited | Heterocyclic compounds |
| CN107641197B (zh) * | 2017-10-30 | 2019-11-22 | 河南工程学院 | 一种以二氧化碳与环氧环己烷为单体的共聚反应催化剂 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2722502B1 (fr) * | 1994-07-12 | 1996-08-23 | Adir | Nouveau derive de benzothiadiazine, son procede depreparation et les compositions pharmaceutiques qui le contiennent |
| JP2002504481A (ja) * | 1998-02-18 | 2002-02-12 | ニューロサーチ、アクティーゼルスカブ | 新規化合物及び陽性ａｍｐａレセプターモジュレーターとしてこれを使用する方法 |
| FR2812291B1 (fr) | 2000-07-28 | 2002-12-13 | Adir | Nouveaux derives de benzothiadiazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
-
2001
- 2001-12-21 FR FR0116621A patent/FR2833956B1/fr not_active Expired - Fee Related
-
2002
- 2002-12-18 AR ARP020104932A patent/AR038028A1/es unknown
- 2002-12-20 EP EP02805408A patent/EP1480986A1/fr not_active Withdrawn
- 2002-12-20 WO PCT/FR2002/004485 patent/WO2003053979A1/fr active Application Filing
- 2002-12-20 US US10/498,948 patent/US7253161B2/en not_active Expired - Fee Related
- 2002-12-20 CN CNB028258126A patent/CN1289509C/zh not_active Expired - Fee Related
- 2002-12-20 NZ NZ533328A patent/NZ533328A/en unknown
- 2002-12-20 HU HU0402585A patent/HUP0402585A3/hu unknown
- 2002-12-20 MX MXPA04005837A patent/MXPA04005837A/es active IP Right Grant
- 2002-12-20 KR KR1020047009302A patent/KR100586685B1/ko not_active IP Right Cessation
- 2002-12-20 PL PL02370159A patent/PL370159A1/xx not_active Application Discontinuation
- 2002-12-20 CA CA002471263A patent/CA2471263A1/fr not_active Abandoned
- 2002-12-20 AU AU2002364674A patent/AU2002364674B2/en not_active Ceased
- 2002-12-20 BR BR0214973-7A patent/BR0214973A/pt not_active IP Right Cessation
- 2002-12-20 GE GE5645A patent/GEP20063759B/en unknown
- 2002-12-20 JP JP2003554695A patent/JP2005518386A/ja active Pending
- 2002-12-20 UA UA20040706011A patent/UA77737C2/uk unknown
- 2002-12-20 EA EA200400758A patent/EA007227B1/ru not_active IP Right Cessation
-
2004
- 2004-06-01 ZA ZA200404294A patent/ZA200404294B/en unknown
- 2004-06-04 MA MA27719A patent/MA27090A1/fr unknown
- 2004-07-14 NO NO20042978A patent/NO20042978L/no not_active Application Discontinuation
-
2005
- 2005-05-30 HK HK05104494A patent/HK1071749A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2833956A1 (fr) | 2003-06-27 |
| CN1289509C (zh) | 2006-12-13 |
| EP1480986A1 (fr) | 2004-12-01 |
| EA200400758A1 (ru) | 2005-06-30 |
| FR2833956B1 (fr) | 2004-01-30 |
| US7253161B2 (en) | 2007-08-07 |
| GEP20063759B (en) | 2006-02-27 |
| WO2003053979A1 (fr) | 2003-07-03 |
| US20050124606A1 (en) | 2005-06-09 |
| CA2471263A1 (fr) | 2003-07-03 |
| AU2002364674B2 (en) | 2007-11-22 |
| MXPA04005837A (es) | 2004-09-10 |
| AU2002364674A1 (en) | 2003-07-09 |
| CN1606560A (zh) | 2005-04-13 |
| HK1071749A1 (en) | 2005-07-29 |
| BR0214973A (pt) | 2004-12-14 |
| JP2005518386A (ja) | 2005-06-23 |
| KR100586685B1 (ko) | 2006-06-08 |
| KR20040073480A (ko) | 2004-08-19 |
| EA007227B1 (ru) | 2006-08-25 |
| HUP0402585A2 (hu) | 2005-03-29 |
| AR038028A1 (es) | 2004-12-22 |
| MA27090A1 (fr) | 2004-12-20 |
| NO20042978L (no) | 2004-07-14 |
| PL370159A1 (en) | 2005-05-16 |
| HUP0402585A3 (en) | 2009-01-28 |
| NZ533328A (en) | 2006-10-27 |
| ZA200404294B (en) | 2005-06-01 |
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