CZ80993A3 - Novel heterocyclic compounds as antagonists of amino acid receptors excitation, processes of their preparation and their use - Google Patents
Novel heterocyclic compounds as antagonists of amino acid receptors excitation, processes of their preparation and their use Download PDFInfo
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- CZ80993A3 CZ80993A3 CS93809A CS8099391A CZ80993A3 CZ 80993 A3 CZ80993 A3 CZ 80993A3 CS 93809 A CS93809 A CS 93809A CS 8099391 A CS8099391 A CS 8099391A CZ 80993 A3 CZ80993 A3 CZ 80993A3
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- compounds
- methylene
- formula
- alkyl
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- 238000000034 method Methods 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title abstract description 5
- 239000005557 antagonist Substances 0.000 title description 7
- 102000015404 Amino Acid Receptors Human genes 0.000 title description 5
- 108010025177 Amino Acid Receptors Proteins 0.000 title description 5
- 230000005284 excitation Effects 0.000 title description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 title description 2
- 230000008569 process Effects 0.000 title description 2
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- 125000000217 alkyl group Chemical group 0.000 claims abstract description 18
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- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 8
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 7
- 230000000202 analgesic effect Effects 0.000 claims abstract description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 4
- 125000003435 aroyl group Chemical group 0.000 claims abstract description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 4
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims abstract description 3
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- 238000010171 animal model Methods 0.000 description 1
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- 238000003556 assay Methods 0.000 description 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 238000012925 biological evaluation Methods 0.000 description 1
- 210000005013 brain tissue Anatomy 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- VQPFDLRNOCQMSN-UHFFFAOYSA-N bromosilane Chemical compound Br[SiH3] VQPFDLRNOCQMSN-UHFFFAOYSA-N 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 239000001913 cellulose Chemical class 0.000 description 1
- 229920002678 cellulose Chemical class 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical class OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- TVZPLCNGKSPOJA-UHFFFAOYSA-N copper zinc Chemical compound [Cu].[Zn] TVZPLCNGKSPOJA-UHFFFAOYSA-N 0.000 description 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- VONWDASPFIQPDY-UHFFFAOYSA-N dimethyl methylphosphonate Chemical compound COP(C)(=O)OC VONWDASPFIQPDY-UHFFFAOYSA-N 0.000 description 1
- HTCGVXPYFNPRRQ-UHFFFAOYSA-N ditert-butyl 3-(2-diethoxyphosphorylacetyl)-4-methylpiperidine-1,2-dicarboxylate Chemical compound CCOP(=O)(OCC)CC(=O)C1C(C)CCN(C(=O)OC(C)(C)C)C1C(=O)OC(C)(C)C HTCGVXPYFNPRRQ-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 125000001145 hydrido group Chemical group *[H] 0.000 description 1
- 230000001146 hypoxic effect Effects 0.000 description 1
- 238000000099 in vitro assay Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000000302 ischemic effect Effects 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- JGZKUKYUQJUUNE-UHFFFAOYSA-L magnesium;ethoxyethane;dibromide Chemical compound [Mg+2].[Br-].[Br-].CCOCC JGZKUKYUQJUUNE-UHFFFAOYSA-L 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 230000016273 neuron death Effects 0.000 description 1
- 230000002981 neuropathic effect Effects 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 229940124641 pain reliever Drugs 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- HXEACLLIILLPRG-UHFFFAOYSA-N pipecolic acid Chemical group OC(=O)C1CCCCN1 HXEACLLIILLPRG-UHFFFAOYSA-N 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- CQPJLZWBXXBTJA-UHFFFAOYSA-N prop-1-ynylphosphonic acid Chemical compound CC#CP(O)(O)=O CQPJLZWBXXBTJA-UHFFFAOYSA-N 0.000 description 1
- QHKCUMSPCMDJCM-UHFFFAOYSA-N propan-2-yl 3-formylpyridine-2-carboxylate Chemical compound CC(C)OC(=O)C1=NC=CC=C1C=O QHKCUMSPCMDJCM-UHFFFAOYSA-N 0.000 description 1
- NSETWVJZUWGCKE-UHFFFAOYSA-N propylphosphonic acid Chemical compound CCCP(O)(O)=O NSETWVJZUWGCKE-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003235 pyrrolidines Chemical class 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012439 solid excipient Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
- SYUQQUMHOZQROL-UHFFFAOYSA-N trimethylsilyl dihydrogen phosphite Chemical compound C[Si](C)(C)OP(O)O SYUQQUMHOZQROL-UHFFFAOYSA-N 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/650952—Six-membered rings having the nitrogen atoms in the positions 1 and 4
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/59—Hydrogenated pyridine rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9003652A SE9003652D0 (sv) | 1990-11-15 | 1990-11-15 | New heterocyclic compounds |
| PCT/SE1991/000753 WO1992008724A1 (en) | 1990-11-15 | 1991-11-07 | New heterocyclic compounds as antagonists of excitatory amino acid receptors, processes for their preparation and their use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CZ80993A3 true CZ80993A3 (en) | 1994-02-16 |
Family
ID=20380925
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS93809A CZ80993A3 (en) | 1990-11-15 | 1991-11-07 | Novel heterocyclic compounds as antagonists of amino acid receptors excitation, processes of their preparation and their use |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP0557375A1 (sv) |
| JP (1) | JPH06502421A (sv) |
| CN (1) | CN1061595A (sv) |
| AU (1) | AU652399B2 (sv) |
| CA (1) | CA2095224A1 (sv) |
| CZ (1) | CZ80993A3 (sv) |
| FI (1) | FI932206A0 (sv) |
| HU (1) | HU9301417D0 (sv) |
| IE (1) | IE913922A1 (sv) |
| IS (1) | IS3782A7 (sv) |
| LT (1) | LTIP1718A (sv) |
| MX (1) | MX9101979A (sv) |
| NO (1) | NO931679D0 (sv) |
| PT (1) | PT99515A (sv) |
| SE (1) | SE9003652D0 (sv) |
| SK (1) | SK46993A3 (sv) |
| WO (1) | WO1992008724A1 (sv) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5194430A (en) * | 1990-05-17 | 1993-03-16 | Merrell Dow Pharmaceuticals Inc. | Heterocyclic-nmda antagonists |
| TW281670B (sv) * | 1993-09-02 | 1996-07-21 | Hoffmann La Roche | |
| US5491241A (en) * | 1993-10-18 | 1996-02-13 | Eli Lilly And Company | Bicyclic intermediates for excitatory amino acid receptor antagonists |
| LT3411358T (lt) | 2016-02-04 | 2022-04-25 | Takeda Pharmaceutical Company Limited | Pakeistas piperidino junginys ir jo naudojimas |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1248531A (en) * | 1984-04-17 | 1989-01-10 | Jeffrey C. Watkins | 4-substituted piperazine-2-carboxylic acids |
| JPS612519A (ja) * | 1984-04-24 | 1986-01-08 | Aron Kasei Co Ltd | 射出成形法 |
| US4906621A (en) * | 1985-05-24 | 1990-03-06 | Ciba-Geigy Corporation | Certain 2-carboxypiperidyl-alkylene phosphonic acids and esters thereof useful for the treatment of disorders responsive to N-methyl-D-aspartate receptor blockade |
| US4740346A (en) * | 1986-02-26 | 1988-04-26 | The Budd Company | Perimeter resin feeding of composite structures |
| JPS63112129A (ja) * | 1986-10-30 | 1988-05-17 | Toyoda Gosei Co Ltd | 多色樹脂成形用金型 |
| IL84492A0 (en) * | 1986-11-21 | 1988-04-29 | Ciba Geigy Ag | Unsaturated phosphonic acids and derivatives |
-
1990
- 1990-11-15 SE SE9003652A patent/SE9003652D0/sv unknown
-
1991
- 1991-11-05 CN CN91110925A patent/CN1061595A/zh active Pending
- 1991-11-07 CA CA002095224A patent/CA2095224A1/en not_active Abandoned
- 1991-11-07 AU AU89391/91A patent/AU652399B2/en not_active Ceased
- 1991-11-07 WO PCT/SE1991/000753 patent/WO1992008724A1/en not_active Application Discontinuation
- 1991-11-07 JP JP4500566A patent/JPH06502421A/ja active Pending
- 1991-11-07 HU HU931417A patent/HU9301417D0/hu unknown
- 1991-11-07 CZ CS93809A patent/CZ80993A3/cs unknown
- 1991-11-07 EP EP91920264A patent/EP0557375A1/en not_active Withdrawn
- 1991-11-07 SK SK46993A patent/SK46993A3/sk unknown
- 1991-11-08 MX MX9101979A patent/MX9101979A/es unknown
- 1991-11-12 IE IE392291A patent/IE913922A1/en unknown
- 1991-11-14 PT PT99515A patent/PT99515A/pt not_active Application Discontinuation
- 1991-11-14 IS IS3782A patent/IS3782A7/is unknown
-
1993
- 1993-05-07 NO NO931679A patent/NO931679D0/no unknown
- 1993-05-14 FI FI932206A patent/FI932206A0/fi not_active Application Discontinuation
- 1993-12-30 LT LTIP1718A patent/LTIP1718A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| NO931679L (no) | 1993-05-07 |
| LTIP1718A (en) | 1995-07-25 |
| HU9301417D0 (en) | 1993-09-28 |
| AU652399B2 (en) | 1994-08-25 |
| CA2095224A1 (en) | 1992-05-16 |
| JPH06502421A (ja) | 1994-03-17 |
| FI932206A (fi) | 1993-05-14 |
| EP0557375A1 (en) | 1993-09-01 |
| SK46993A3 (en) | 1993-10-06 |
| MX9101979A (es) | 1992-07-08 |
| AU8939191A (en) | 1992-06-11 |
| SE9003652D0 (sv) | 1990-11-15 |
| IE913922A1 (en) | 1992-05-20 |
| IS3782A7 (is) | 1992-05-16 |
| FI932206A0 (fi) | 1993-05-14 |
| NO931679D0 (no) | 1993-05-07 |
| PT99515A (pt) | 1992-09-30 |
| CN1061595A (zh) | 1992-06-03 |
| WO1992008724A1 (en) | 1992-05-29 |
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