JP2012521973A5 - - Google Patents
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- Publication number
- JP2012521973A5 JP2012521973A5 JP2012501315A JP2012501315A JP2012521973A5 JP 2012521973 A5 JP2012521973 A5 JP 2012521973A5 JP 2012501315 A JP2012501315 A JP 2012501315A JP 2012501315 A JP2012501315 A JP 2012501315A JP 2012521973 A5 JP2012521973 A5 JP 2012521973A5
- Authority
- JP
- Japan
- Prior art keywords
- vivo
- contrast agent
- formula
- precursor compound
- vivo imaging
- 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
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- 150000001875 compounds Chemical class 0.000 claims description 16
- 239000002243 precursor Substances 0.000 claims description 13
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 230000002285 radioactive effect Effects 0.000 claims description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 2
- 239000002872 contrast media Substances 0.000 claims 11
- 238000001727 in vivo Methods 0.000 claims 11
- 238000000034 method Methods 0.000 claims 9
- 238000011503 in vivo imaging Methods 0.000 claims 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000003725 azepanyl group Chemical group 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 239000012216 imaging agent Substances 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- 229910052717 sulfur Chemical group 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000003636 chemical group Chemical group 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 239000001301 oxygen Chemical group 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 239000012217 radiopharmaceutical Substances 0.000 claims 1
- 229940121896 radiopharmaceutical Drugs 0.000 claims 1
- 230000002799 radiopharmaceutical effect Effects 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 239000011593 sulfur Chemical group 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- -1 aryl diazonium salts Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- KRHYYFGTRYWZRS-BJUDXGSMSA-M fluorine-18(1-) Chemical compound [18F-] KRHYYFGTRYWZRS-BJUDXGSMSA-M 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16413109P | 2009-03-27 | 2009-03-27 | |
| GBGB0905328.1A GB0905328D0 (en) | 2009-03-27 | 2009-03-27 | Indole derivatives |
| GB0905328.1 | 2009-03-27 | ||
| US61/164,131 | 2009-03-27 | ||
| PCT/EP2010/053998 WO2010109007A2 (en) | 2009-03-27 | 2010-03-26 | Indole derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012521973A JP2012521973A (ja) | 2012-09-20 |
| JP2012521973A5 true JP2012521973A5 (enExample) | 2014-11-13 |
| JP5651163B2 JP5651163B2 (ja) | 2015-01-07 |
Family
ID=40671850
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012501315A Active JP5651163B2 (ja) | 2009-03-27 | 2010-03-26 | Ｐｂｒリガンドとしての三環系インドール誘導体 |
Country Status (17)
| Country | Link |
|---|---|
| US (2) | US8790619B2 (enExample) |
| EP (1) | EP2411362B1 (enExample) |
| JP (1) | JP5651163B2 (enExample) |
| KR (1) | KR101692090B1 (enExample) |
| CN (1) | CN102448933B (enExample) |
| AU (1) | AU2010227527B2 (enExample) |
| BR (1) | BRPI1010261A2 (enExample) |
| CA (1) | CA2756887C (enExample) |
| ES (1) | ES2635310T3 (enExample) |
| GB (1) | GB0905328D0 (enExample) |
| IL (1) | IL215019A0 (enExample) |
| MX (1) | MX2011010154A (enExample) |
| NZ (1) | NZ595227A (enExample) |
| RU (1) | RU2525196C2 (enExample) |
| SG (1) | SG174589A1 (enExample) |
| WO (1) | WO2010109007A2 (enExample) |
| ZA (1) | ZA201106708B (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0905328D0 (en) | 2009-03-27 | 2009-05-13 | Ge Healthcare Ltd | Indole derivatives |
| SG183837A1 (en) * | 2010-03-26 | 2012-10-30 | Ge Healthcare Ltd | Tricyclic indole derivatives as pbr ligands |
| GB201016038D0 (en) | 2010-09-24 | 2010-11-10 | Ge Healthcare Ltd | In vivo imaging method |
| GB201016411D0 (en) * | 2010-09-30 | 2010-11-10 | Ge Healthcare Ltd | In vivo imaging method for cancer |
| GB201021263D0 (en) * | 2010-12-15 | 2011-01-26 | Ge Healthcare Ltd | Solid phase extraction method |
| EP2694505B1 (en) * | 2011-04-05 | 2022-04-27 | Sloan-kettering Institute For Cancer Research | Hsp90 inhibitors |
| US20140301947A1 (en) | 2011-06-06 | 2014-10-09 | Imperial Innovations Limited | Methods to predict binding affinity of tspo imaging agents to tspo |
| AU2012315757B9 (en) * | 2011-09-30 | 2018-01-25 | Ge Healthcare Limited | Calibration and normalization systems and methods for radiopharmaceutical synthesizers |
| US10709798B2 (en) | 2012-11-30 | 2020-07-14 | Ge Healthcare Limited | Crystallization process of tricyclic indole derivatives |
| CN104797559A (zh) * | 2012-11-30 | 2015-07-22 | 通用电气健康护理有限公司 | 卤化锌介导的环化过程得到三环吲哚 |
| GB201312768D0 (en) | 2013-07-17 | 2013-08-28 | Ge Healthcare Ltd | Work-up procedure |
| GB201316762D0 (en) * | 2013-09-20 | 2013-11-06 | Ge Healthcare Ltd | Novel compounds |
| GB201316766D0 (en) * | 2013-09-20 | 2013-11-06 | Ge Healthcare Uk Ltd | Macrophage Imaging |
| GB201316764D0 (en) * | 2013-09-20 | 2013-11-06 | Ge Healthcare Ltd | Novel compounds |
| KR102668112B1 (ko) | 2014-12-04 | 2024-05-23 | 지이 헬쓰케어 리미티드 | 방사성 약제로부터의 아세트알데히드의 제거 방법 |
| CN106748802B (zh) * | 2016-12-26 | 2018-11-13 | 南京理工大学 | 一种制备含氟仲胺的方法 |
| WO2018218025A1 (en) * | 2017-05-24 | 2018-11-29 | The Trustees Of The University Of Pennsylvania | Radiolabeled and fluorescent parp inhibitors for imaging and radiotherapy |
| US11200669B2 (en) * | 2019-11-19 | 2021-12-14 | Uih America, Inc. | Systems and methods for determining plasma input function used in positron emission tomography imaging |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3939177A (en) * | 1972-11-22 | 1976-02-17 | Sterling Drug Inc. | 4-Aminomethyl-9-benzyl-1,2,3,4-tetrahydrocarbazoles |
| US3979391A (en) * | 1972-11-22 | 1976-09-07 | Sterling Drug Inc. | 1,2,3,4-Tetrahydrocarbazoles |
| FR2599740B1 (fr) * | 1986-06-05 | 1988-08-12 | Rhone Poulenc Sante | Derives de benzo(b)thiophene de benzo(b)furannecarboxamides, leurs procedes de preparation et les medicaments les contenant |
| US5270030A (en) * | 1988-12-29 | 1993-12-14 | Bio-Technology General Corp. | Fibrin binding domain polypeptide and method of producing |
| WO1999025340A1 (en) | 1997-11-14 | 1999-05-27 | Eli Lilly And Company | Treatment for alzheimer's disease |
| JPH11228539A (ja) * | 1997-12-03 | 1999-08-24 | Taisho Pharmaceut Co Ltd | 含窒素四環性化合物 |
| US6281355B1 (en) * | 1997-12-03 | 2001-08-28 | Taisho Pharmaceutical Co., Ltd. | Nitrogen-containing tetracyclic compounds |
| DE69930308T2 (de) * | 1998-12-11 | 2006-11-30 | Virginia Commonwealth University | Selektive 5-ht 6-rezeptor-liganden |
| FR2788776B1 (fr) | 1999-01-26 | 2001-02-23 | Synthelabo | Derives de 4-oxo-3, 5-dihydro-4h-pyridazino [4,5-b] indole-1 -carboxamide, leur preparation et leur application en therapeutique |
| GB0115929D0 (en) | 2001-06-29 | 2001-08-22 | Nycomed Amersham Plc | Solid-phase electrophilic fluorination |
| GB0115927D0 (en) | 2001-06-29 | 2001-08-22 | Nycomed Amersham Plc | Solid-phase nucleophilic fluorination |
| JP2005527464A (ja) | 2001-08-09 | 2005-09-15 | イーライ・リリー・アンド・カンパニー | ｓＰＬＡ２インヒビターとしてのシクロヘプタＢインドール誘導体 |
| JP2005527466A (ja) | 2001-08-09 | 2005-09-15 | イーライ・リリー・アンド・カンパニー | ｓＰＬＡ２インヒビターとしてのシクロヘプトＢインドール誘導体 |
| GB0523506D0 (en) | 2005-11-18 | 2005-12-28 | Hammersmith Imanet Ltd | Novel in vivo imaging compounds |
| GB0905328D0 (en) | 2009-03-27 | 2009-05-13 | Ge Healthcare Ltd | Indole derivatives |
-
2009
- 2009-03-27 GB GBGB0905328.1A patent/GB0905328D0/en not_active Ceased
-
2010
- 2010-03-26 RU RU2011138850/04A patent/RU2525196C2/ru active
- 2010-03-26 JP JP2012501315A patent/JP5651163B2/ja active Active
- 2010-03-26 ES ES10710356.6T patent/ES2635310T3/es active Active
- 2010-03-26 AU AU2010227527A patent/AU2010227527B2/en active Active
- 2010-03-26 SG SG2011070018A patent/SG174589A1/en unknown
- 2010-03-26 BR BRPI1010261A patent/BRPI1010261A2/pt not_active Application Discontinuation
- 2010-03-26 US US13/258,465 patent/US8790619B2/en active Active
- 2010-03-26 CN CN201080023868.3A patent/CN102448933B/zh active Active
- 2010-03-26 MX MX2011010154A patent/MX2011010154A/es active IP Right Grant
- 2010-03-26 KR KR1020117025305A patent/KR101692090B1/ko active Active
- 2010-03-26 WO PCT/EP2010/053998 patent/WO2010109007A2/en not_active Ceased
- 2010-03-26 CA CA2756887A patent/CA2756887C/en active Active
- 2010-03-26 NZ NZ595227A patent/NZ595227A/xx unknown
- 2010-03-26 EP EP10710356.6A patent/EP2411362B1/en active Active
- 2010-09-13 US US12/880,218 patent/US8501153B2/en active Active
-
2011
- 2011-09-07 IL IL215019A patent/IL215019A0/en not_active IP Right Cessation
- 2011-09-13 ZA ZA2011/06708A patent/ZA201106708B/en unknown
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