JP4624105B2 - アリールアミジン誘導体を含む抗真菌薬 - Google Patents
アリールアミジン誘導体を含む抗真菌薬 Download PDFInfo
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- JP4624105B2 JP4624105B2 JP2004546028A JP2004546028A JP4624105B2 JP 4624105 B2 JP4624105 B2 JP 4624105B2 JP 2004546028 A JP2004546028 A JP 2004546028A JP 2004546028 A JP2004546028 A JP 2004546028A JP 4624105 B2 JP4624105 B2 JP 4624105B2
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- 229940121375 antifungal agent Drugs 0.000 title claims description 42
- 239000003429 antifungal agent Substances 0.000 title description 20
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 29
- -1 hydroxy, mercapto Chemical class 0.000 claims abstract description 28
- 150000003839 salts Chemical class 0.000 claims abstract description 20
- 239000002253 acid Substances 0.000 claims abstract description 19
- 150000007513 acids Chemical class 0.000 claims abstract description 17
- 230000003287 optical effect Effects 0.000 claims abstract description 6
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- 230000000843 anti-fungal effect Effects 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 18
- 241000222122 Candida albicans Species 0.000 claims description 14
- 229940095731 candida albicans Drugs 0.000 claims description 14
- 241001225321 Aspergillus fumigatus Species 0.000 claims description 13
- 229940091771 aspergillus fumigatus Drugs 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
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- VHVPQPYKVGDNFY-DFMJLFEVSA-N 2-[(2r)-butan-2-yl]-4-[4-[4-[4-[[(2r,4s)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-1,2,4-triazol-3-one Chemical compound O=C1N([C@H](C)CC)N=CN1C1=CC=C(N2CCN(CC2)C=2C=CC(OC[C@@H]3O[C@](CN4N=CN=C4)(OC3)C=3C(=CC(Cl)=CC=3)Cl)=CC=2)C=C1 VHVPQPYKVGDNFY-DFMJLFEVSA-N 0.000 claims description 9
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
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- QRJJEGAJXVEBNE-MOHJPFBDSA-N oxiconazole Chemical compound ClC1=CC(Cl)=CC=C1CO\N=C(C=1C(=CC(Cl)=CC=1)Cl)\CN1C=NC=C1 QRJJEGAJXVEBNE-MOHJPFBDSA-N 0.000 claims description 3
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- DOMXUEMWDBAQBQ-WEVVVXLNSA-N terbinafine Chemical compound C1=CC=C2C(CN(C\C=C\C#CC(C)(C)C)C)=CC=CC2=C1 DOMXUEMWDBAQBQ-WEVVVXLNSA-N 0.000 claims description 3
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- BCEHBSKCWLPMDN-MGPLVRAMSA-N voriconazole Chemical compound C1([C@H](C)[C@](O)(CN2N=CN=C2)C=2C(=CC(F)=CC=2)F)=NC=NC=C1F BCEHBSKCWLPMDN-MGPLVRAMSA-N 0.000 claims description 3
- WWJFFVUVFNBJTN-UIBIZFFUSA-N (2S)-2-[[(2S,3S,4S)-2-amino-4-hydroxy-4-(5-hydroxypyridin-2-yl)-3-methylbutanoyl]amino]-2-[(2R,3S,4S,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]acetic acid Chemical class C[C@@H]([C@H](N)C(=O)N[C@@H]([C@H]1O[C@H]([C@@H](O)[C@@H]1O)n1ccc(=O)[nH]c1=O)C(O)=O)[C@H](O)c1ccc(O)cn1 WWJFFVUVFNBJTN-UIBIZFFUSA-N 0.000 claims description 2
- OCAPBUJLXMYKEJ-UHFFFAOYSA-N 1-[biphenyl-4-yl(phenyl)methyl]imidazole Chemical compound C1=NC=CN1C(C=1C=CC(=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 OCAPBUJLXMYKEJ-UHFFFAOYSA-N 0.000 claims description 2
- APKFDSVGJQXUKY-KKGHZKTASA-N Amphotericin-B Natural products O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1C=CC=CC=CC=CC=CC=CC=C[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-KKGHZKTASA-N 0.000 claims description 2
- 229930184499 Nikkomycin Natural products 0.000 claims description 2
- APKFDSVGJQXUKY-INPOYWNPSA-N amphotericin B Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-INPOYWNPSA-N 0.000 claims description 2
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- ZCJYUTQZBAIHBS-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)-2-{[4-(phenylsulfanyl)benzyl]oxy}ethyl]imidazole Chemical compound ClC1=CC(Cl)=CC=C1C(OCC=1C=CC(SC=2C=CC=CC=2)=CC=1)CN1C=NC=C1 ZCJYUTQZBAIHBS-UHFFFAOYSA-N 0.000 claims 1
- QXHHHPZILQDDPS-UHFFFAOYSA-N 1-{2-[(2-chloro-3-thienyl)methoxy]-2-(2,4-dichlorophenyl)ethyl}imidazole Chemical compound S1C=CC(COC(CN2C=NC=C2)C=2C(=CC(Cl)=CC=2)Cl)=C1Cl QXHHHPZILQDDPS-UHFFFAOYSA-N 0.000 claims 1
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- 238000012458 antifungal assay Methods 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical class NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000005968 oxazolinyl group Chemical group 0.000 description 1
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000009044 synergistic interaction Effects 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 238000003026 viability measurement method Methods 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/155—Amidines (), e.g. guanidine (H2N—C(=NH)—NH2), isourea (N=C(OH)—NH2), isothiourea (—N=C(SH)—NH2)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02356210A EP1413301A1 (fr) | 2002-10-24 | 2002-10-24 | Médicaments antifongiques à base de dérivés d'arylamidine |
| PCT/EP2003/013335 WO2004037239A1 (en) | 2002-10-24 | 2003-10-24 | Antifungal medicaments based on arylamidine derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2006505576A JP2006505576A (ja) | 2006-02-16 |
| JP2006505576A5 JP2006505576A5 (enExample) | 2006-07-20 |
| JP4624105B2 true JP4624105B2 (ja) | 2011-02-02 |
Family
ID=32050123
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004546028A Expired - Fee Related JP4624105B2 (ja) | 2002-10-24 | 2003-10-24 | アリールアミジン誘導体を含む抗真菌薬 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20060052459A1 (enExample) |
| EP (2) | EP1413301A1 (enExample) |
| JP (1) | JP4624105B2 (enExample) |
| AT (1) | ATE452630T1 (enExample) |
| AU (1) | AU2003292131A1 (enExample) |
| CA (1) | CA2502433A1 (enExample) |
| DE (1) | DE60330702D1 (enExample) |
| WO (1) | WO2004037239A1 (enExample) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1570736A1 (en) * | 2004-03-05 | 2005-09-07 | Bayer CropScience S.A. | Fungicide composition comprising an arylamidine derivative and known fungicide compounds |
| BRPI0616000B1 (pt) * | 2005-09-13 | 2016-04-19 | Bayer Cropscience Ag | composto derivado de fenil-amidina, processo de preparação de composto, composto derivado de nitrofeniléter, composto derivado de aminofeniléter, método de controle de fungos fitopatogênicos de safras e método de controle de insetos daninhos. |
| EP1969931A1 (de) | 2007-03-12 | 2008-09-17 | Bayer CropScience Aktiengesellschaft | Fluoalkylphenylamidine und deren Verwendung als Fungizide |
| BRPI0808798A2 (pt) | 2007-03-12 | 2014-10-07 | Bayer Cropscience Ag | Fenoxifenilamidinas 3,5-dissubstituídas e seu uso como fungicidas |
| EP1969929A1 (de) | 2007-03-12 | 2008-09-17 | Bayer CropScience AG | Substituierte Phenylamidine und deren Verwendung als Fungizide |
| EP1969934A1 (de) * | 2007-03-12 | 2008-09-17 | Bayer CropScience AG | 4-Cycloalkyl-oder 4-arylsubstituierte Phenoxyphenylamidine und deren Verwendung als Fungizide |
| EP1969933A1 (de) * | 2007-03-12 | 2008-09-17 | Bayer CropScience AG | Dihalogenphenoxyphenylamidine und deren Verwendung als Fungizide |
| EP1969935A1 (de) * | 2007-03-12 | 2008-09-17 | Bayer CropScience AG | 3,4-Disubstituierte Phenoxyphenylamidine und deren Verwendung als Fungizide |
| WO2008110279A1 (de) * | 2007-03-12 | 2008-09-18 | Bayer Cropscience Ag | Dihalogenphenoxyphenylamidine und deren verwendung als fungizide |
| EP1969930A1 (de) * | 2007-03-12 | 2008-09-17 | Bayer CropScience AG | Phenoxyphenylamidine und deren Verwendung als Fungizide |
| EP1969932A1 (de) * | 2007-03-12 | 2008-09-17 | Bayer CropScience AG | Phenoxyphenylamidine und deren Verwendung als Fungizide |
| BRPI0808846A2 (pt) | 2007-03-12 | 2019-09-24 | Bayer Cropscience Ag | fenoxifenilamidinas 3-substituídas e seu uso como fungicidas |
| US8168567B2 (en) * | 2007-04-19 | 2012-05-01 | Bayer Cropscience Ag | Thiadiazolyl oxyphenyl amidines and the use thereof as a fungicide |
| EP2072506A1 (de) | 2007-12-21 | 2009-06-24 | Bayer CropScience AG | Thiazolyloxyphenylamidine oder Thiadiazolyloxyphenylamidine und deren Verwendung als Fungizide |
| CN102066347B (zh) * | 2008-06-27 | 2016-06-08 | 拜耳知识产权有限责任公司 | 噻二唑氧苯基脒及其作为杀菌剂的应用 |
| UA106875C2 (uk) | 2008-06-27 | 2014-10-27 | Баєр Кропсаєнс Аг | Тіадіазолілоксифеніламідини та їх застосування як фунгіцидів |
| EP2223917A1 (de) | 2009-02-02 | 2010-09-01 | Bayer CropScience AG | Isothiazolyloxyphenylamidine und deren Verwendung als Fungizide |
| EP2264011A1 (de) | 2009-06-03 | 2010-12-22 | Bayer CropScience AG | Heteroarylamidine und deren Verwendung als Fungizide |
| EP2264012A1 (de) | 2009-06-03 | 2010-12-22 | Bayer CropScience AG | Heteroarylamidine und deren Verwendung als Fungizide |
| WO2011006604A1 (de) | 2009-07-17 | 2011-01-20 | Bayer Cropscience Ag | Substituierte aminothiazole und deren verwendung als fungizide |
| WO2011082941A1 (de) | 2009-12-16 | 2011-07-14 | Bayer Cropscience Ag | Benzylsubstituierte thiadiazolyloxyphenylamidiniumsalze als fungizide |
| WO2012019998A1 (de) | 2010-08-10 | 2012-02-16 | Bayer Cropscience Ag | Herstellung von n'-(4-{[3-(4-chlorbenzyl)-1,2,4-thiadiazol-5-yl]oxy}-2,5-dimethylphenyl)-n-ethyl-n-methylimidoformamid |
| ES2563232T3 (es) | 2011-07-29 | 2016-03-11 | Taisho Pharmaceutical Co., Ltd. | Compuesto de amidina o sal del mismo |
| WO2013076666A1 (en) * | 2011-11-23 | 2013-05-30 | Newsouth Innovations Pty Limited | Antimicrobial peptides and uses thereof |
| WO2016043260A1 (ja) * | 2014-09-19 | 2016-03-24 | 塩野義製薬株式会社 | 環状グアニジンまたはアミジン化合物 |
| HUE051950T2 (hu) | 2015-06-15 | 2021-04-28 | Bayer Cropscience Ag | Halogén-szubsztituált fenoxifenilamidinok és alkalmazásuk fungicidként |
| EP3307706B1 (en) | 2015-06-15 | 2019-07-24 | Bayer CropScience AG | Halogen-substituted phenoxyphenylamidines and the use thereof as fungicides |
| EP3319937A1 (en) | 2015-07-08 | 2018-05-16 | Bayer CropScience Aktiengesellschaft | Phenoxyhalogenphenylamidines and the use thereof as fungicides |
| EP3335559A1 (en) | 2016-12-14 | 2018-06-20 | Bayer CropScience Aktiengesellschaft | Active compound combinations |
| BR112019012272A2 (pt) | 2016-12-14 | 2019-12-03 | Bayer Ag | fenilamidinas e seu uso como fungicidas |
| BR112019012219A2 (pt) | 2016-12-14 | 2019-11-12 | Bayer Cropscience Aktiengesellschaft | fenoxifenilamidinas e o uso das mesmas como fungicidas |
| WO2018109002A1 (en) | 2016-12-14 | 2018-06-21 | Bayer Cropscience Aktiengesellschaft | Active compound combinations |
| EP3708565A1 (en) | 2020-03-04 | 2020-09-16 | Bayer AG | Pyrimidinyloxyphenylamidines and the use thereof as fungicides |
| EP3915971A1 (en) | 2020-12-16 | 2021-12-01 | Bayer Aktiengesellschaft | Phenyl-s(o)n-phenylamidines and the use thereof as fungicides |
| CN121717732A (zh) * | 2024-09-21 | 2026-03-24 | 青岛清原化合物有限公司 | 苯基脒类化合物及其应用 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3217770A1 (de) * | 1982-05-12 | 1983-11-17 | Hoechst Ag, 6230 Frankfurt | 1-(1,3-dioxolan-2-yl-methyl)-1h-imidazole und -1h-1,2,4-triazole und deren salze, verfahren zu ihrer herstellung, sie enthaltende mittel und ihre verwendung |
| EP0957101A1 (en) * | 1998-05-14 | 1999-11-17 | Janssen Pharmaceutica N.V. | Water soluble azoles as broad-spectrum antifungals |
| GB9902592D0 (en) * | 1999-02-06 | 1999-03-24 | Hoechst Schering Agrevo Gmbh | Fungicides |
| EP1278755A2 (en) * | 2000-03-07 | 2003-01-29 | Ranbaxy Laboratories, Limited | Azole compounds as therapeutic agents for fungal infections |
| EP1178038A1 (en) * | 2000-08-04 | 2002-02-06 | Aventis Cropscience S.A. | Fungicidal phenylamidine derivatives |
| EP1337510A4 (en) * | 2000-11-06 | 2005-02-23 | Univ North Carolina | SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF NEW DICATIONIC REVERSED AMIDINES |
-
2002
- 2002-10-24 EP EP02356210A patent/EP1413301A1/fr not_active Withdrawn
-
2003
- 2003-10-24 WO PCT/EP2003/013335 patent/WO2004037239A1/en not_active Ceased
- 2003-10-24 JP JP2004546028A patent/JP4624105B2/ja not_active Expired - Fee Related
- 2003-10-24 AT AT03767675T patent/ATE452630T1/de not_active IP Right Cessation
- 2003-10-24 DE DE60330702T patent/DE60330702D1/de not_active Expired - Lifetime
- 2003-10-24 US US10/532,033 patent/US20060052459A1/en not_active Abandoned
- 2003-10-24 CA CA002502433A patent/CA2502433A1/en not_active Abandoned
- 2003-10-24 EP EP03767675A patent/EP1562569B1/en not_active Expired - Lifetime
- 2003-10-24 AU AU2003292131A patent/AU2003292131A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US20060052459A1 (en) | 2006-03-09 |
| ATE452630T1 (de) | 2010-01-15 |
| EP1413301A1 (fr) | 2004-04-28 |
| EP1562569A1 (en) | 2005-08-17 |
| JP2006505576A (ja) | 2006-02-16 |
| CA2502433A1 (en) | 2004-05-06 |
| AU2003292131A1 (en) | 2004-05-13 |
| EP1562569B1 (en) | 2009-12-23 |
| WO2004037239A1 (en) | 2004-05-06 |
| DE60330702D1 (de) | 2010-02-04 |
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