EA023578B1 - C28-амины c3-модифицированных производных бетулиновой кислоты в качестве ингибиторов созревания вич - Google Patents

Info

Publication number

EA023578B1

EA023578B1 EA201391098A EA201391098A EA023578B1 EA 023578 B1 EA023578 B1 EA 023578B1 EA 201391098 A EA201391098 A EA 201391098A EA 201391098 A EA201391098 A EA 201391098A EA 023578 B1 EA023578 B1 EA 023578B1

Authority

EA

Eurasian Patent Office

Prior art keywords

alkyl

group

methyl

prop

pentamethyl

Prior art date

2011-01-31

Links

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• Global Dossier
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• 150000001412 amines Chemical class 0.000 title abstract description 246
• 239000003112 inhibitor Substances 0.000 title abstract description 37
• QGJZLNKBHJESQX-FZFNOLFKSA-N betulinic acid Chemical class C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C(=C)C)[C@@H]5[C@H]4CC[C@@H]3[C@]21C QGJZLNKBHJESQX-FZFNOLFKSA-N 0.000 title abstract description 11
• 230000035800 maturation Effects 0.000 title abstract description 9
• 238000000034 method Methods 0.000 claims abstract description 409
• 150000001875 compounds Chemical class 0.000 claims abstract description 290
• 150000003839 salts Chemical class 0.000 claims abstract description 17
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
• 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 claims description 282
• 125000000217 alkyl group Chemical group 0.000 claims description 140
• 241000725303 Human immunodeficiency virus Species 0.000 claims description 44
• 125000001072 heteroaryl group Chemical group 0.000 claims description 40
• 125000004429 atom Chemical group 0.000 claims description 30
• 125000003118 aryl group Chemical group 0.000 claims description 25
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
• 229910052736 halogen Inorganic materials 0.000 claims description 16
• 125000004432 carbon atom Chemical group C* 0.000 claims description 15
• 125000003545 alkoxy group Chemical group 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
• 125000001424 substituent group Chemical group 0.000 claims description 13
• 125000002950 monocyclic group Chemical group 0.000 claims description 10
• 208000036142 Viral infection Diseases 0.000 claims description 9
• 239000003085 diluting agent Substances 0.000 claims description 9
• 229910052757 nitrogen Inorganic materials 0.000 claims description 9
• 230000009385 viral infection Effects 0.000 claims description 9
• 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 8
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
• 229910052700 potassium Inorganic materials 0.000 claims description 6
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 150000002367 halogens Chemical class 0.000 claims description 5
• 229910052739 hydrogen Inorganic materials 0.000 claims description 5
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
• 229910052760 oxygen Inorganic materials 0.000 claims description 5
• 239000001301 oxygen Substances 0.000 claims description 5
• 125000006413 ring segment Chemical group 0.000 claims description 5
• 229910052717 sulfur Inorganic materials 0.000 claims description 5
• 239000011593 sulfur Substances 0.000 claims description 5
• 241000124008 Mammalia Species 0.000 claims description 4
• 125000003367 polycyclic group Chemical group 0.000 claims description 4
• 229940110676 inzo Drugs 0.000 claims 1
• 208000030507 AIDS Diseases 0.000 abstract description 84
• 238000011282 treatment Methods 0.000 abstract description 20
• 229940079593 drug Drugs 0.000 abstract description 16
• 239000003814 drug Substances 0.000 abstract description 16
• 230000000840 anti-viral effect Effects 0.000 abstract description 3
• -1 -C 3-6 cycloalkyl Chemical group 0.000 description 675
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 339
• 238000002360 preparation method Methods 0.000 description 277
• 235000010233 benzoic acid Nutrition 0.000 description 234
• 239000005711 Benzoic acid Substances 0.000 description 218
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 214
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 186
• 239000000203 mixture Substances 0.000 description 182
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 173
• 239000000243 solution Substances 0.000 description 168
• 239000007787 solid Substances 0.000 description 145
• 239000003153 chemical reaction reagent Substances 0.000 description 139
• 239000000047 product Substances 0.000 description 131
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 105
• HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 description 97
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 91
• 239000002904 solvent Substances 0.000 description 88
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 81
• 230000007062 hydrolysis Effects 0.000 description 79
• 238000006460 hydrolysis reaction Methods 0.000 description 79
• 208000031886 HIV Infections Diseases 0.000 description 66
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 66
• 208000037357 HIV infectious disease Diseases 0.000 description 65
• 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 65
• 230000002829 reductive effect Effects 0.000 description 54
• 150000001408 amides Chemical class 0.000 description 53
• 239000012043 crude product Substances 0.000 description 52
• 238000002953 preparative HPLC Methods 0.000 description 50
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 44
• 238000000746 purification Methods 0.000 description 44
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 42
• 230000015572 biosynthetic process Effects 0.000 description 40
• 239000012044 organic layer Substances 0.000 description 37
• 239000011541 reaction mixture Substances 0.000 description 34
• 239000000126 substance Substances 0.000 description 34
• 238000003786 synthesis reaction Methods 0.000 description 32
• 239000000706 filtrate Substances 0.000 description 28
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 25
• 238000001914 filtration Methods 0.000 description 24
• 239000012321 sodium triacetoxyborohydride Substances 0.000 description 24
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
• 239000002274 desiccant Substances 0.000 description 21
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
• 239000000725 suspension Substances 0.000 description 21
• 238000004458 analytical method Methods 0.000 description 20
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 18
• 150000001299 aldehydes Chemical class 0.000 description 17
• 150000001559 benzoic acids Chemical class 0.000 description 17
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 16
• 238000006243 chemical reaction Methods 0.000 description 16
• 239000006260 foam Substances 0.000 description 16
• 239000002585 base Substances 0.000 description 15
• 239000000460 chlorine Substances 0.000 description 15
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 15
• PDLNHDSYGLTYDS-UHFFFAOYSA-N 3-aminopropanoic acid;hydrochloride Chemical compound Cl.NCCC(O)=O PDLNHDSYGLTYDS-UHFFFAOYSA-N 0.000 description 14
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
• 238000005903 acid hydrolysis reaction Methods 0.000 description 14
• 210000004027 cell Anatomy 0.000 description 14
• QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 14
• 125000003373 pyrazinyl group Chemical group 0.000 description 14
• 229920006395 saturated elastomer Polymers 0.000 description 14
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 13
• 241000700605 Viruses Species 0.000 description 13
• 125000000753 cycloalkyl group Chemical group 0.000 description 13
• 230000000694 effects Effects 0.000 description 13
• 238000003818 flash chromatography Methods 0.000 description 13
• 229910052938 sodium sulfate Inorganic materials 0.000 description 13
• 235000011152 sodium sulphate Nutrition 0.000 description 13
• 238000003756 stirring Methods 0.000 description 13
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
• XQSPYNMVSIKCOC-NTSWFWBYSA-N Emtricitabine Chemical compound C1=C(F)C(N)=NC(=O)N1[C@H]1O[C@@H](CO)SC1 XQSPYNMVSIKCOC-NTSWFWBYSA-N 0.000 description 12
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 12
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
• 239000000741 silica gel Substances 0.000 description 12
• 229910002027 silica gel Inorganic materials 0.000 description 12
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
• 239000003795 chemical substances by application Substances 0.000 description 11
• COQRGFWWJBEXRC-UHFFFAOYSA-N hydron;methyl 2-aminoacetate;chloride Chemical compound Cl.COC(=O)CN COQRGFWWJBEXRC-UHFFFAOYSA-N 0.000 description 11
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 11
• 239000000137 peptide hydrolase inhibitor Substances 0.000 description 11
• USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 10
• 239000005695 Ammonium acetate Substances 0.000 description 10
• 235000019257 ammonium acetate Nutrition 0.000 description 10
• 229940043376 ammonium acetate Drugs 0.000 description 10
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 10
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 10
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
• 125000006308 propyl amino group Chemical group 0.000 description 10
• 229940124158 Protease/peptidase inhibitor Drugs 0.000 description 9
• 150000004657 carbamic acid derivatives Chemical class 0.000 description 9
• 229940002612 prodrug Drugs 0.000 description 9
• 239000000651 prodrug Substances 0.000 description 9
• VCMJCVGFSROFHV-WZGZYPNHSA-N tenofovir disoproxil fumarate Chemical compound OC(=O)\C=C\C(O)=O.N1=CN=C2N(C[C@@H](C)OCP(=O)(OCOC(=O)OC(C)C)OCOC(=O)OC(C)C)C=NC2=C1N VCMJCVGFSROFHV-WZGZYPNHSA-N 0.000 description 9
• 108090000565 Capsid Proteins Proteins 0.000 description 8
• 102100023321 Ceruloplasmin Human genes 0.000 description 8
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 8
• 238000010511 deprotection reaction Methods 0.000 description 8
• 238000010438 heat treatment Methods 0.000 description 8
• 150000004702 methyl esters Chemical class 0.000 description 8
• 238000006268 reductive amination reaction Methods 0.000 description 8
• 239000011734 sodium Substances 0.000 description 8
• 239000007858 starting material Substances 0.000 description 8
• 238000004809 thin layer chromatography Methods 0.000 description 8
• 208000007766 Kaposi sarcoma Diseases 0.000 description 7
• FVWJYYTZTCVBKE-ROUWMTJPSA-N betulin Chemical class C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(CO)CC[C@@H](C(=C)C)[C@@H]5[C@H]4CC[C@@H]3[C@]21C FVWJYYTZTCVBKE-ROUWMTJPSA-N 0.000 description 7
• 239000013058 crude material Substances 0.000 description 7
• 238000011161 development Methods 0.000 description 7
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
• 229960001936 indinavir Drugs 0.000 description 7
• CBVCZFGXHXORBI-PXQQMZJSSA-N indinavir Chemical compound C([C@H](N(CC1)C[C@@H](O)C[C@@H](CC=2C=CC=CC=2)C(=O)N[C@H]2C3=CC=CC=C3C[C@H]2O)C(=O)NC(C)(C)C)N1CC1=CC=CN=C1 CBVCZFGXHXORBI-PXQQMZJSSA-N 0.000 description 7
• 229940095102 methyl benzoate Drugs 0.000 description 7
• 239000012071 phase Substances 0.000 description 7
• 125000000547 substituted alkyl group Chemical group 0.000 description 7
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 7
• WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
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• 108060001084 Luciferase Proteins 0.000 description 6
• JYDNKGUBLIKNAM-UHFFFAOYSA-N Oxyallobutulin Natural products C1CC(=O)C(C)(C)C2CCC3(C)C4(C)CCC5(CO)CCC(C(=C)C)C5C4CCC3C21C JYDNKGUBLIKNAM-UHFFFAOYSA-N 0.000 description 6
• ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Chemical compound OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 6
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• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
• 239000012445 acidic reagent Substances 0.000 description 6
• 125000004104 aryloxy group Chemical group 0.000 description 6
• KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 6
• MVIRREHRVZLANQ-UHFFFAOYSA-N betulin Natural products CC(=O)OC1CCC2(C)C(CCC3(C)C2CC=C4C5C(CCC5(CO)CCC34C)C(=C)C)C1(C)C MVIRREHRVZLANQ-UHFFFAOYSA-N 0.000 description 6
• 229910052799 carbon Inorganic materials 0.000 description 6
• WHBIGIKBNXZKFE-UHFFFAOYSA-N delavirdine Chemical compound CC(C)NC1=CC=CN=C1N1CCN(C(=O)C=2NC3=CC=C(NS(C)(=O)=O)C=C3C=2)CC1 WHBIGIKBNXZKFE-UHFFFAOYSA-N 0.000 description 6
• PEASPLKKXBYDKL-FXEVSJAOSA-N enfuvirtide Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(C)=O)[C@@H](C)O)[C@@H](C)CC)C1=CN=CN1 PEASPLKKXBYDKL-FXEVSJAOSA-N 0.000 description 6
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• BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 6
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• 125000005190 thiohydroxy group Chemical group 0.000 description 6
• ONDSBJMLAHVLMI-UHFFFAOYSA-N trimethylsilyldiazomethane Chemical compound C[Si](C)(C)[CH-][N+]#N ONDSBJMLAHVLMI-UHFFFAOYSA-N 0.000 description 6
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 5
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• NQDJXKOVJZTUJA-UHFFFAOYSA-N nevirapine Chemical compound C12=NC=CC=C2C(=O)NC=2C(C)=CC=NC=2N1C1CC1 NQDJXKOVJZTUJA-UHFFFAOYSA-N 0.000 description 5
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• 239000003419 rna directed dna polymerase inhibitor Substances 0.000 description 5
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• 125000005404 thioheteroaryloxy group Chemical group 0.000 description 5
• HJORCZCMNWLHMB-UHFFFAOYSA-N 1-(3-aminopropyl)pyrrolidin-2-one Chemical compound NCCCN1CCCC1=O HJORCZCMNWLHMB-UHFFFAOYSA-N 0.000 description 4
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• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
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