JP2014506869A5 - - Google Patents
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- JP2014506869A5 JP2014506869A5 JP2013533311A JP2013533311A JP2014506869A5 JP 2014506869 A5 JP2014506869 A5 JP 2014506869A5 JP 2013533311 A JP2013533311 A JP 2013533311A JP 2013533311 A JP2013533311 A JP 2013533311A JP 2014506869 A5 JP2014506869 A5 JP 2014506869A5
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- JP
- Japan
- Prior art keywords
- alkyl
- aryl
- group
- target
- independently
- 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.)
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- 239000000523 sample Substances 0.000 claims description 149
- 125000000217 alkyl group Chemical group 0.000 claims description 85
- 125000003118 aryl group Chemical group 0.000 claims description 67
- 238000000034 method Methods 0.000 claims description 66
- 238000006243 chemical reaction Methods 0.000 claims description 62
- 238000003384 imaging method Methods 0.000 claims description 62
- 239000012636 effector Substances 0.000 claims description 54
- 150000001875 compounds Chemical class 0.000 claims description 49
- 239000003153 chemical reaction reagent Substances 0.000 claims description 47
- 238000006742 Retro-Diels-Alder reaction Methods 0.000 claims description 32
- 125000001424 substituent group Chemical group 0.000 claims description 31
- 150000001993 dienes Chemical class 0.000 claims description 30
- URYYVOIYTNXXBN-OWOJBTEDSA-N trans-cyclooctene Chemical compound C1CCC\C=C\CC1 URYYVOIYTNXXBN-OWOJBTEDSA-N 0.000 claims description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims description 25
- 125000005647 linker group Chemical group 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- -1 N 3 Inorganic materials 0.000 claims description 17
- 230000027455 binding Effects 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 16
- 125000006850 spacer group Chemical group 0.000 claims description 16
- 230000008685 targeting Effects 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 230000001225 therapeutic effect Effects 0.000 claims description 13
- 229910004013 NO 2 Inorganic materials 0.000 claims description 12
- 238000011282 treatment Methods 0.000 claims description 12
- 229910052786 argon Inorganic materials 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 241001465754 Metazoa Species 0.000 claims description 7
- 150000001721 carbon Chemical group 0.000 claims description 7
- 238000002059 diagnostic imaging Methods 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 239000000376 reactant Substances 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 238000002560 therapeutic procedure Methods 0.000 claims description 7
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical class N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 229910052727 yttrium Inorganic materials 0.000 claims description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 230000000155 isotopic effect Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 109
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 92
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- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 description 65
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 54
- 206010028980 Neoplasm Diseases 0.000 description 48
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 45
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- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 37
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 34
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
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- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 24
- 229920001223 polyethylene glycol Polymers 0.000 description 24
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- 238000005481 NMR spectroscopy Methods 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 241000699666 Mus <mouse, genus> Species 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 18
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- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 14
- 238000001914 filtration Methods 0.000 description 14
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical group ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 13
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- 239000000377 silicon dioxide Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
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- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 11
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- 150000004905 tetrazines Chemical class 0.000 description 9
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| EP2709666B1 (en) * | 2011-05-16 | 2021-07-14 | Koninklijke Philips N.V. | Bio-orthogonal drug activation |
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| WO2014081300A1 (en) * | 2012-11-22 | 2014-05-30 | Tagworks Pharmaceuticals B.V. | Channel protein activatable liposomes |
| US20150297741A1 (en) * | 2012-11-22 | 2015-10-22 | Tagworks Pharmaceuticals B.V. | Bio-orthogonal drug activation |
| US20150359913A1 (en) * | 2013-01-25 | 2015-12-17 | Memorial Sloan-Kettering Cancer Center | Tetrazines/trans-cyclooctenes in solid phase synthesis of labeled peptides |
| US9110230B2 (en) | 2013-05-07 | 2015-08-18 | Corning Incorporated | Scratch-resistant articles with retained optical properties |
| US9366784B2 (en) | 2013-05-07 | 2016-06-14 | Corning Incorporated | Low-color scratch-resistant articles with a multilayer optical film |
| EP3010486B1 (en) | 2013-06-19 | 2023-11-22 | The Regents of The University of California | Chemical structures for localized delivery of therapeutic agents |
| ES2694723T3 (es) | 2014-01-04 | 2018-12-26 | Craniovation, Inc. | Dispositivo para su uso en terapia fotodinámica |
| WO2015117235A1 (en) * | 2014-02-10 | 2015-08-13 | Mcmaster University | Targeted molecular imaging contrast agents |
| AU2015229014B2 (en) | 2014-03-14 | 2019-07-25 | The Regents Of The University Of California | TCO conjugates and methods for delivery of therapeutic agents |
| JP6787789B2 (ja) * | 2014-04-04 | 2020-11-18 | プレジデント アンド フェローズ オブ ハーバード カレッジ | 詰め替え可能な薬物送達デバイスおよびその使用方法 |
| US11267973B2 (en) | 2014-05-12 | 2022-03-08 | Corning Incorporated | Durable anti-reflective articles |
| US9790593B2 (en) | 2014-08-01 | 2017-10-17 | Corning Incorporated | Scratch-resistant materials and articles including the same |
| WO2016025480A1 (en) | 2014-08-11 | 2016-02-18 | The General Hospital Corporation | Cyclooctenes for bioorthogonol reactions |
| CN108135857A (zh) | 2015-09-10 | 2018-06-08 | 沙思奇公司 | 生物正交组合物 |
| EP3770649A1 (en) | 2015-09-14 | 2021-01-27 | Corning Incorporated | High light transmission and scratch-resistant anti-reflective articles |
| EP3153155B1 (en) * | 2015-10-08 | 2021-03-03 | President and Fellows of Harvard College | Refillable drug delivery devices and methods of use thereof |
| US11617799B2 (en) * | 2016-06-27 | 2023-04-04 | Tagworks Pharmaceuticals B.V. | Cleavable tetrazine used in bio-orthogonal drug activation |
| AU2018250312C1 (en) | 2017-04-07 | 2024-08-22 | Tambo, Inc. | Bioorthogonal compositions |
| US11560384B2 (en) | 2017-05-04 | 2023-01-24 | University Of Utah Research Foundation | Benzonorbornadiene derivatives and reactions thereof |
| WO2018204872A2 (en) * | 2017-05-05 | 2018-11-08 | Fusion Pharmaceuticals Inc. | Igf-1r monoclonal antibodies and uses thereof |
| EP3651741A4 (en) | 2017-07-14 | 2021-04-21 | The Penn State Research Foundation | COMPOSITIONS AND METHODS OF TARGETED DELIVERY OF A THERAPEUTIC AND / OR DIAGNOSTIC SPECIES |
| GB201720769D0 (en) | 2017-12-13 | 2018-01-24 | Univ Of Northumbria At Newcastle | Pericyclic reactions |
| JP2021506842A (ja) | 2017-12-18 | 2021-02-22 | ヤンセン バイオテツク，インコーポレーテツド | ポリペプチドの放射性標識 |
| CA3099419A1 (en) | 2018-05-04 | 2019-11-07 | Tagworks Pharmaceuticals B.V. | Tetrazines for high click conjugation yield in vivo and high click release yield |
| AU2019262521B2 (en) | 2018-05-04 | 2024-04-18 | Tagworks Pharmaceuticals B.V. | Compounds comprising a linker for increasing transcyclooctene stability |
| KR102591065B1 (ko) | 2018-08-17 | 2023-10-19 | 코닝 인코포레이티드 | 얇고, 내구성 있는 반사-방지 구조를 갖는 무기산화물 물품 |
| JP7337174B2 (ja) | 2018-09-18 | 2023-09-01 | ニカング セラピューティクス， インコーポレイテッド | Ｓｒｃホモロジー－２ホスファターゼ阻害剤としての三置換ヘテロアリール誘導体 |
| CN113677397A (zh) | 2019-02-13 | 2021-11-19 | 阿尔菲斯医疗股份有限公司 | 无创声动力学治疗 |
| AU2020282737A1 (en) | 2019-05-29 | 2021-12-16 | Sonalasense, Inc. | Sonosensitization |
| WO2020256546A1 (en) | 2019-06-17 | 2020-12-24 | Tagworks Pharmaceuticals B.V. | Compounds for fast and efficient click release |
| CA3143924C (en) | 2019-06-17 | 2025-06-03 | Tagworks Pharmaceuticals B.V. | Agents that allow in vivo cleavage of markers linked to biomolecules |
| US12386101B2 (en) | 2020-07-09 | 2025-08-12 | Corning Incorporated | Textured region of a substrate to reduce specular reflectance incorporating surface features with an elliptical perimeter or segments thereof, and method of making the same |
| CA3185803A1 (en) | 2020-08-07 | 2022-02-10 | Vijay Agarwal | Ultrasound arrays for enhanced sonodynamic therapy for treating cancer |
| JP2023537066A (ja) | 2020-08-07 | 2023-08-30 | タンボ・インコーポレイテッド | トランス－シクロオクテン生体直交型薬剤並びに癌及び免疫療法における使用 |
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| EP4108669A1 (en) * | 2021-06-24 | 2022-12-28 | Institute Of Organic Chemistry And Biochemistry As CR, V.V.I. | Carbohydrate derivatives and kits for cell surface labeling |
| WO2023244185A1 (en) * | 2022-06-13 | 2023-12-21 | Fikrettin Sahin | Use of lutetium salt compounds for antiviral effect |
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| US5326856A (en) | 1992-04-09 | 1994-07-05 | Cytogen Corporation | Bifunctional isothiocyanate derived thiocarbonyls as ligands for metal binding |
| EP2026840A2 (en) * | 2005-10-04 | 2009-02-25 | Koninklijke Philips Electronics N.V. | Targeted imaging and/or therapy using the [3+2]-azide-alkyne cycloaddition |
| CN102271712B (zh) * | 2008-10-31 | 2015-11-25 | 通用医疗公司 | 用于将物质递送至生物靶标的组合物和方法 |
| WO2010119389A2 (en) | 2009-04-16 | 2010-10-21 | Koninklijke Philips Electronics N.V. | Pretargeting kit, method and agents used therein |
| WO2012049624A1 (en) * | 2010-10-14 | 2012-04-19 | Koninklijke Philips Electronics N.V. | Pretargeting kit, method and agents used therein |
| US10927139B2 (en) * | 2012-11-22 | 2021-02-23 | Tagworks Pharmaceuticals B.V. | Chemically cleavable group |
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