JP6842415B2 - 放射性医薬品からアセトアルデヒドを除去する方法 - Google Patents
放射性医薬品からアセトアルデヒドを除去する方法 Download PDFInfo
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- JP6842415B2 JP6842415B2 JP2017527839A JP2017527839A JP6842415B2 JP 6842415 B2 JP6842415 B2 JP 6842415B2 JP 2017527839 A JP2017527839 A JP 2017527839A JP 2017527839 A JP2017527839 A JP 2017527839A JP 6842415 B2 JP6842415 B2 JP 6842415B2
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- acetaldehyde
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- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 title claims description 76
- 239000012217 radiopharmaceutical Substances 0.000 title claims description 26
- 229940121896 radiopharmaceutical Drugs 0.000 title claims description 26
- 230000002799 radiopharmaceutical effect Effects 0.000 title claims description 26
- 238000000034 method Methods 0.000 claims description 34
- 239000002516 radical scavenger Substances 0.000 claims description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 19
- 238000009472 formulation Methods 0.000 claims description 15
- 230000015572 biosynthetic process Effects 0.000 claims description 11
- 238000002600 positron emission tomography Methods 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 239000000700 radioactive tracer Substances 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
- 150000001299 aldehydes Chemical class 0.000 description 30
- 239000008194 pharmaceutical composition Substances 0.000 description 18
- 238000004817 gas chromatography Methods 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 239000000546 pharmaceutical excipient Substances 0.000 description 7
- 238000003908 quality control method Methods 0.000 description 7
- 239000000523 sample Substances 0.000 description 7
- ZWDVQMVZZYIAHO-UHFFFAOYSA-N 2-fluorobenzaldehyde Chemical compound FC1=CC=CC=C1C=O ZWDVQMVZZYIAHO-UHFFFAOYSA-N 0.000 description 6
- 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 description 6
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 230000002285 radioactive effect Effects 0.000 description 5
- 238000009826 distribution Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 239000000825 pharmaceutical preparation Substances 0.000 description 4
- 229940127557 pharmaceutical product Drugs 0.000 description 4
- 238000010791 quenching Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 238000011503 in vivo imaging Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 230000000171 quenching effect Effects 0.000 description 3
- VXFFXZSNVKXXIB-SCSBXPEDSA-N 2-[(1r,4s,10r,13s,16r,19s,25s)-10-[2-[2-[2-[2-[[2-(2-amino-2-oxoethoxy)acetyl]amino]ethoxy]ethoxy]ethoxy]ethylcarbamoyl]-13-benzyl-25-[3-(diaminomethylideneamino)propyl]-4-[4-[[2-[2-[2-[2-[2-[2-[2-[2-[[2-[(e)-(4-fluorophenyl)methylideneamino]oxyacetyl]ami Chemical compound C([C@@H]1NC(=O)CSC[C@H](NC(=O)[C@H](CC=2C=CC=CC=2)NC(=O)[C@@H]2CSSC[C@@H](C(N[C@@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(=O)N2)=O)NC1=O)C(=O)NCCOCCOCCOCCNC(=O)COCC(=O)N)CCCNC(=O)COCC(=O)NCCOCCOCCOCCOCCOCCNC(=O)CO\N=C\C1=CC=C(F)C=C1 VXFFXZSNVKXXIB-SCSBXPEDSA-N 0.000 description 2
- 108010092045 AH 111585 Proteins 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- KRHYYFGTRYWZRS-BJUDXGSMSA-M fluorine-18(1-) Chemical compound [18F-] KRHYYFGTRYWZRS-BJUDXGSMSA-M 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000037361 pathway Effects 0.000 description 2
- 238000011002 quantification Methods 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- UOQXIWFBQSVDPP-COJKEBBMSA-N 4-fluoranylbenzaldehyde Chemical compound [18F]C1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-COJKEBBMSA-N 0.000 description 1
- 208000005189 Embolism Diseases 0.000 description 1
- MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000013060 biological fluid Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000011859 microparticle Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000011146 sterile filtration Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/42—Proteins; Polypeptides; Degradation products thereof; Derivatives thereof, e.g. albumin, gelatin or zein
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/041—Heterocyclic compounds
- A61K51/044—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins
- A61K51/0453—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/62—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being a protein, peptide or polyamino acid
- A61K47/64—Drug-peptide, drug-protein or drug-polyamino acid conjugates, i.e. the modifying agent being a peptide, protein or polyamino acid which is covalently bonded or complexed to a therapeutically active agent
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/041—Heterocyclic compounds
- A61K51/044—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins
- A61K51/0446—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/08—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/08—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins
- A61K51/082—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins the peptide being a RGD-containing peptide
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/15—Medicinal preparations ; Physical properties thereof, e.g. dissolubility
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K41/00—Medicinal preparations obtained by treating materials with wave energy or particle radiation ; Therapies using these preparations
- A61K41/0038—Radiosensitizing, i.e. administration of pharmaceutical agents that enhance the effect of radiotherapy
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
Description
本発明では、アルデヒドスカベンジャーは、アミノ−オキシ末端を有する分子であり得る。アミノ−オキシ官能基は極めて反応性であることが知られており、例えば、1ppmの濃度でアセトンを室温においてほぼ完全に変換することができる。
(i)医薬製剤中の遊離アミノオキシ含有賦形剤、
(ii)医薬製剤を通過させる、結合アミノキシ含有官能基を含有する固相材料、
(iii)個々の用量/QC/マイクロ/保持試料バイアルの初回分配の際に使用される分配流体経路の一部としてのカートリッジ/濾過ユニットの一部、
(iv)臨床使用の直前の分配に使用される分配流体経路の一部としてのカートリッジ/濾過ユニットの一部、
(v)放射性トレーサの製造直後に、患者用量投与のためにシリンジを充填するときに医薬製剤を通過させるカートリッジ/濾過ユニットの一部、及び/又は
(vi)臨床使用の直前に、患者用量投与のためにシリンジを充填するときに医薬製剤を通過させるカートリッジ/濾過ユニット
として提供することができる。
本発明では、医薬製剤は最終放射性医薬製剤を指すものとする。一実施形態では、医薬製剤は、哺乳動物投与に適切な形態であり、無菌で、発熱物質非含有の、毒性及び有害事象を起こす化合物を含まない、生体適合性のpH(およそpH4.0から10.5)において製剤化された製剤を意味する。このような製剤は、インビボで塞栓を引き起こし得るリスクのある微粒子を含まず、生物学的流体(例えば血液)との接触において沈降を起こさないように製剤化される。このような製剤はさらに、生物学的に適合性の賦形剤、好ましくは等張性の賦形剤だけを含有する。本発明では、医薬製剤は放射性医薬品及び溶媒を含み、各々は本明細書に記載されている。医薬製剤は、限定するものではないが、自動合成機(例えば、FASTlab(登録商標))を含む当分野で公知の任意の手段によって製造することができる。
本発明では、放射性医薬品は、インビトロ又はインビボイメージングに適切な任意の放射標識化合物を含むことができる。本発明の一実施形態では、放射標識化合物は、インビボイメージングに適切である。インビボイメージングに適切であるために、放射性医薬品は哺乳動物投与に適した形態で適切に提供され、哺乳動物対象単独をイメージングすることによって得られる画像よりも、目的の領域又は器官においてより鮮明な画像の提供を支援する。好ましい実施形態では、放射性医薬品は、陽電子放射断層撮影(PET)トレーサである。好ましい実施形態では、放射性医薬品は、18F PETトレーサである。適切な18F PETトレーサの非限定的な例としては、以下の[18F]フルシクラチド、[18F]フルテメタモール、及び[18F]GE180が挙げられるが、これらに限定されない。
本発明では、溶媒は、医薬製剤における使用に適切な、当分野において公知の任意の有機溶媒を含んでよい。好ましい実施形態では、溶媒はアルコールを含む。好ましい実施形態では、溶媒はエタノール、イソプロパノール又はバイオアルコールである。好ましい実施形態では、溶媒はエタノールである。
HPLCを使用してフルシクラチド(18F)注射液試料中のアセトアルデヒド含有量を分析する実験において、アセトアルデヒドを、AH111695を用いてUV吸収性フルシクラチド類似体AH111930に誘導化した(スキーム1)。
Claims (8)
- アルデヒドスカベンジャーを放射性医薬製剤と組合せるステップを含む、前記放射性医薬製剤中のアセトアルデヒドの形成を制御するための方法であって、
アルデヒドスカベンジャーが以下の構造を有する、方法。
- 前記放射性医薬製剤が放射性医薬品及び溶媒を含む、請求項1に記載の方法。
- 前記放射性医薬品が陽電子放射断層撮影(PET)トレーサである、請求項2に記載の方法。
- 前記放射性医薬品が18F PETトレーサである、請求項3に記載の方法。
- 前記放射性医薬品が以下の化合物の群から選択される、請求項4に記載の方法。
- 前記溶媒がアルコールを含む、請求項2乃至請求項5のいずれか1項に記載の方法。
- 前記アルコールが、エタノール、イソプロパノール及びバイオアルコールからなる群から選択される、請求項6に記載の方法。
- 前記アルコールがエタノールである、請求項7に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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US201462087371P | 2014-12-04 | 2014-12-04 | |
US62/087,371 | 2014-12-04 | ||
PCT/EP2015/078682 WO2016087653A1 (en) | 2014-12-04 | 2015-12-04 | Method of removing acetaldehyde from radioactive pharmaceuticals |
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JP2018504369A JP2018504369A (ja) | 2018-02-15 |
JP6842415B2 true JP6842415B2 (ja) | 2021-03-17 |
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JP2020196848A Active JP7164583B2 (ja) | 2014-12-04 | 2020-11-27 | 放射性医薬品からアセトアルデヒドを除去する方法 |
JP2022168399A Active JP7379638B2 (ja) | 2014-12-04 | 2022-10-20 | 放射性医薬品からアセトアルデヒドを除去する方法 |
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JP2022168399A Active JP7379638B2 (ja) | 2014-12-04 | 2022-10-20 | 放射性医薬品からアセトアルデヒドを除去する方法 |
Country Status (9)
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US (3) | US10660966B2 (ja) |
EP (1) | EP3226884B1 (ja) |
JP (3) | JP6842415B2 (ja) |
KR (2) | KR102458116B1 (ja) |
CN (1) | CN106999603B (ja) |
AU (1) | AU2015356971B2 (ja) |
IL (1) | IL252186B (ja) |
RU (1) | RU2719399C2 (ja) |
WO (1) | WO2016087653A1 (ja) |
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US10660966B2 (en) | 2014-12-04 | 2020-05-26 | Ge Healthcare Limited | Method for removing acetaldehyde |
US11969764B2 (en) | 2016-07-18 | 2024-04-30 | Sortera Technologies, Inc. | Sorting of plastics |
Family Cites Families (20)
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MC2260A1 (fr) * | 1990-06-18 | 1993-04-26 | Dow Chemical Co | Formulations de produits radiopharmaceutiques,leur methode d'administration et leur procede de preparation |
US5130255A (en) * | 1990-12-13 | 1992-07-14 | Genentech, Inc. | Process for preparing storage stable pharmaceuticals |
WO2002083210A1 (en) * | 2001-04-13 | 2002-10-24 | Jean-Luc Morelle | Process and device for preparing radiopharmaceutical products for injection |
JP2004073377A (ja) * | 2002-08-13 | 2004-03-11 | Takeda Chem Ind Ltd | 固形医薬組成物中の有効成分の安定化方法 |
AU2003301654A1 (en) * | 2002-10-22 | 2004-05-13 | Dainippon Pharmaceutical Co., Ltd. | Stabilized composition |
GB0305704D0 (en) | 2003-03-13 | 2003-04-16 | Amersham Plc | Radiofluorination methods |
GB0410448D0 (en) | 2004-05-11 | 2004-06-16 | Hammersmith Imanet Ltd | Purification methods |
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WO2009027452A2 (en) | 2007-08-30 | 2009-03-05 | Ge Healthcare Limited | Radiopharmaceutical composition |
JP5318874B2 (ja) * | 2007-09-10 | 2013-10-16 | ジーイー・ヘルスケア・リミテッド | 放射性フッ素化方法 |
CA2703518A1 (en) * | 2007-11-07 | 2009-05-14 | Ge Healthcare Bv | Stabilization of radiopharmaceuticals |
GB0905328D0 (en) | 2009-03-27 | 2009-05-13 | Ge Healthcare Ltd | Indole derivatives |
WO2011044410A2 (en) | 2009-10-08 | 2011-04-14 | Ge Healthcare Limited | Solid phase extraction purification method |
EP2552891B1 (en) | 2010-03-26 | 2018-08-08 | GE Healthcare Limited | Tricyclic indole derivatives as pbr ligands |
EP2648767B1 (en) * | 2010-12-09 | 2023-03-15 | GE Healthcare Limited | Radiotracer compositions |
GB201021263D0 (en) | 2010-12-15 | 2011-01-26 | Ge Healthcare Ltd | Solid phase extraction method |
GB201202420D0 (en) | 2012-02-13 | 2012-03-28 | Ge Healthcare Ltd | Radiotracer compositions |
US9605078B2 (en) * | 2012-11-16 | 2017-03-28 | The Regents Of The University Of California | Pictet-Spengler ligation for protein chemical modification |
US10660966B2 (en) | 2014-12-04 | 2020-05-26 | Ge Healthcare Limited | Method for removing acetaldehyde |
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