CA2822583A1 - Use of aniline in the radiostabilization of oxime ligation reactions - Google Patents
Use of aniline in the radiostabilization of oxime ligation reactions Download PDFInfo
- Publication number
- CA2822583A1 CA2822583A1 CA2822583A CA2822583A CA2822583A1 CA 2822583 A1 CA2822583 A1 CA 2822583A1 CA 2822583 A CA2822583 A CA 2822583A CA 2822583 A CA2822583 A CA 2822583A CA 2822583 A1 CA2822583 A1 CA 2822583A1
- Authority
- CA
- Canada
- Prior art keywords
- radiostabilizing
- radiolabeled
- aniline
- aldehyde
- organic
- 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.)
- Abandoned
Links
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 title claims abstract description 93
- 150000002923 oximes Chemical class 0.000 title abstract description 9
- 238000006243 chemical reaction Methods 0.000 title description 22
- 238000000034 method Methods 0.000 claims abstract description 48
- 150000001299 aldehydes Chemical class 0.000 claims description 41
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims description 26
- 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 238000003384 imaging method Methods 0.000 claims description 8
- 238000002603 single-photon emission computed tomography Methods 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 150000001413 amino acids Chemical class 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 5
- 239000013598 vector Substances 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 2
- HUMNYLRZRPPJDN-KWCOIAHCSA-N benzaldehyde Chemical group O=[11CH]C1=CC=CC=C1 HUMNYLRZRPPJDN-KWCOIAHCSA-N 0.000 claims 1
- 238000005755 formation reaction Methods 0.000 abstract description 3
- 150000002466 imines Chemical class 0.000 abstract 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 13
- 108010092045 AH 111585 Proteins 0.000 description 13
- 230000021615 conjugation Effects 0.000 description 9
- 101800001442 Peptide pr Proteins 0.000 description 6
- WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 description 4
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 description 3
- -1 aniline compound Chemical class 0.000 description 3
- 150000001448 anilines Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 102000004196 processed proteins & peptides Human genes 0.000 description 3
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 2
- WCBPJVKVIMMEQC-UHFFFAOYSA-N 1,1-diphenyl-2-(2,4,6-trinitrophenyl)hydrazine Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1NN(C=1C=CC=CC=1)C1=CC=CC=C1 WCBPJVKVIMMEQC-UHFFFAOYSA-N 0.000 description 2
- RVWUHFFPEOKYLB-UHFFFAOYSA-N 2,2,6,6-tetramethyl-1-oxidopiperidin-1-ium Chemical compound CC1(C)CCCC(C)(C)[NH+]1[O-] RVWUHFFPEOKYLB-UHFFFAOYSA-N 0.000 description 2
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 2
- ZWDVQMVZZYIAHO-COJKEBBMSA-N 2-fluoranylbenzaldehyde Chemical compound [18F]C1=CC=CC=C1C=O ZWDVQMVZZYIAHO-COJKEBBMSA-N 0.000 description 2
- VCUVETGKTILCLC-UHFFFAOYSA-N 5,5-dimethyl-1-pyrroline N-oxide Chemical compound CC1(C)CCC=[N+]1[O-] VCUVETGKTILCLC-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 238000012879 PET imaging Methods 0.000 description 2
- 229960004050 aminobenzoic acid Drugs 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000012831 peritoneal equilibrium test Methods 0.000 description 2
- 238000012636 positron electron tomography Methods 0.000 description 2
- 238000012877 positron emission topography Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- SKDGWNHUETZZCS-UHFFFAOYSA-N 2,3-ditert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(O)=C1C(C)(C)C SKDGWNHUETZZCS-UHFFFAOYSA-N 0.000 description 1
- ZWDVQMVZZYIAHO-UHFFFAOYSA-N 2-fluorobenzaldehyde Chemical compound FC1=CC=CC=C1C=O ZWDVQMVZZYIAHO-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- OENHQHLEOONYIE-UKMVMLAPSA-N all-trans beta-carotene Natural products CC=1CCCC(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C OENHQHLEOONYIE-UKMVMLAPSA-N 0.000 description 1
- SQISUZWPWJHTEP-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1.NC1=CC=CC=C1 SQISUZWPWJHTEP-UHFFFAOYSA-N 0.000 description 1
- TUPZEYHYWIEDIH-WAIFQNFQSA-N beta-carotene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C)C=CC=C(/C)C=CC2=CCCCC2(C)C TUPZEYHYWIEDIH-WAIFQNFQSA-N 0.000 description 1
- 235000013734 beta-carotene Nutrition 0.000 description 1
- 239000011648 beta-carotene Substances 0.000 description 1
- 229960002747 betacarotene Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 1
- 230000005595 deprotonation Effects 0.000 description 1
- 238000010537 deprotonation reaction Methods 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229960005219 gentisic acid Drugs 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000002414 normal-phase solid-phase extraction Methods 0.000 description 1
- 238000003415 nucleophilic catalysis Methods 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N trans-Stilbene Natural products C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N trans-stilbene Chemical group C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/64—Cyclic peptides containing only normal peptide links
-
- 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
-
- 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
- A61K51/0497—Organic compounds conjugates with a carrier being an organic compounds
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Optics & Photonics (AREA)
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201061425399P | 2010-12-21 | 2010-12-21 | |
| US61/425,399 | 2010-12-21 | ||
| PCT/US2011/065036 WO2012087725A1 (en) | 2010-12-21 | 2011-12-15 | Use of aniline iν the radiostabilization of oxime ligation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2822583A1 true CA2822583A1 (en) | 2012-06-28 |
Family
ID=45509655
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2822583A Abandoned CA2822583A1 (en) | 2010-12-21 | 2011-12-15 | Use of aniline in the radiostabilization of oxime ligation reactions |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US9567372B2 (https=) |
| EP (1) | EP2654798B1 (https=) |
| JP (1) | JP6067580B2 (https=) |
| KR (1) | KR20130132941A (https=) |
| CN (1) | CN103370084B (https=) |
| AU (1) | AU2011349698A1 (https=) |
| BR (1) | BR112013015580A2 (https=) |
| CA (1) | CA2822583A1 (https=) |
| ES (1) | ES2739504T3 (https=) |
| MX (1) | MX2013007364A (https=) |
| NZ (1) | NZ612151A (https=) |
| RU (1) | RU2013128354A (https=) |
| SG (1) | SG191218A1 (https=) |
| WO (1) | WO2012087725A1 (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201209082D0 (en) * | 2012-05-24 | 2012-07-04 | Ge Healthcare Ltd | Purification method |
| GB201314936D0 (en) | 2013-08-21 | 2013-10-02 | Ge Healthcare Ltd | Radiolabelling method |
| GB201322456D0 (en) | 2013-12-18 | 2014-02-05 | Ge Healthcare Ltd | Radiotracer compositions and methods |
| GB201805253D0 (en) * | 2018-03-29 | 2018-05-16 | Ge Healthcare Ltd Ip | Solid phase extraction |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3274621D1 (en) * | 1981-10-30 | 1987-01-22 | Amersham Int Plc | Radiopharmaceutical composition based on technetium-99m and reagent for making it |
| GB0015242D0 (en) * | 2000-06-22 | 2000-08-16 | Nycomed Amersham Plc | Stabiliser for radiopharmaceuticals |
| US20040080492A1 (en) | 2002-10-23 | 2004-04-29 | Chen Hung Hua | Fingerprint access control mouse |
| GB0224799D0 (en) | 2002-10-25 | 2002-12-04 | Amersham Plc | Improved complex compositions |
| GB0305704D0 (en) | 2003-03-13 | 2003-04-16 | Amersham Plc | Radiofluorination methods |
| GB0420344D0 (en) * | 2004-09-14 | 2004-10-13 | Amersham Plc | Diagnostic compounds |
| GB0522112D0 (en) | 2005-10-29 | 2005-12-07 | Ge Healthcare Ltd | Novel imaging agents for cancer |
| GB0718967D0 (en) | 2007-09-28 | 2007-11-07 | Ge Healthcare Ltd | Peptide imaging agents |
-
2011
- 2011-12-15 CN CN201180068013.7A patent/CN103370084B/zh active Active
- 2011-12-15 AU AU2011349698A patent/AU2011349698A1/en not_active Abandoned
- 2011-12-15 CA CA2822583A patent/CA2822583A1/en not_active Abandoned
- 2011-12-15 BR BR112013015580A patent/BR112013015580A2/pt not_active IP Right Cessation
- 2011-12-15 KR KR1020137019149A patent/KR20130132941A/ko not_active Withdrawn
- 2011-12-15 US US13/996,020 patent/US9567372B2/en active Active
- 2011-12-15 EP EP11811223.4A patent/EP2654798B1/en active Active
- 2011-12-15 NZ NZ612151A patent/NZ612151A/en not_active IP Right Cessation
- 2011-12-15 MX MX2013007364A patent/MX2013007364A/es not_active Application Discontinuation
- 2011-12-15 RU RU2013128354/04A patent/RU2013128354A/ru not_active Application Discontinuation
- 2011-12-15 JP JP2013546219A patent/JP6067580B2/ja active Active
- 2011-12-15 SG SG2013046784A patent/SG191218A1/en unknown
- 2011-12-15 WO PCT/US2011/065036 patent/WO2012087725A1/en not_active Ceased
- 2011-12-15 ES ES11811223T patent/ES2739504T3/es active Active
Also Published As
| Publication number | Publication date |
|---|---|
| RU2013128354A (ru) | 2015-01-27 |
| AU2011349698A1 (en) | 2013-07-25 |
| JP2014508126A (ja) | 2014-04-03 |
| SG191218A1 (en) | 2013-07-31 |
| US20130274436A1 (en) | 2013-10-17 |
| CN103370084A (zh) | 2013-10-23 |
| EP2654798B1 (en) | 2019-07-03 |
| ES2739504T3 (es) | 2020-01-31 |
| BR112013015580A2 (pt) | 2016-10-04 |
| EP2654798A1 (en) | 2013-10-30 |
| WO2012087725A1 (en) | 2012-06-28 |
| KR20130132941A (ko) | 2013-12-05 |
| JP6067580B2 (ja) | 2017-01-25 |
| US9567372B2 (en) | 2017-02-14 |
| MX2013007364A (es) | 2014-03-21 |
| CN103370084B (zh) | 2016-11-09 |
| NZ612151A (en) | 2015-08-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20161215 |