NZ578556A - Antiviral nucleoside analogs - Google Patents

Info

Publication number

NZ578556A

NZ578556A NZ578556A NZ57855608A NZ578556A NZ 578556 A NZ578556 A NZ 578556A NZ 578556 A NZ578556 A NZ 578556A NZ 57855608 A NZ57855608 A NZ 57855608A NZ 578556 A NZ578556 A NZ 578556A

Authority

NZ

New Zealand

Prior art keywords

substituted

alkyl

aryl

alkenyl

alkynyl

Prior art date

2007-01-12

Links

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• 239000002777 nucleoside Substances 0.000 title claims description 15
• 150000003833 nucleoside derivatives Chemical class 0.000 title description 11
• 230000000840 anti-viral effect Effects 0.000 title description 8
• 150000001875 compounds Chemical class 0.000 claims abstract description 172
• 239000003814 drug Substances 0.000 claims abstract description 30
• 125000001424 substituent group Chemical group 0.000 claims abstract description 30
• 208000036142 Viral infection Diseases 0.000 claims abstract description 25
• 230000009385 viral infection Effects 0.000 claims abstract description 25
• 241000725303 Human immunodeficiency virus Species 0.000 claims abstract description 7
• 208000005176 Hepatitis C Diseases 0.000 claims abstract description 6
• 238000004519 manufacturing process Methods 0.000 claims abstract description 6
• 241000710886 West Nile virus Species 0.000 claims abstract description 5
• 208000002672 hepatitis B Diseases 0.000 claims abstract description 5
• 201000011001 Ebola Hemorrhagic Fever Diseases 0.000 claims abstract description 4
• 241001115402 Ebolavirus Species 0.000 claims abstract description 4
• 241001466953 Echovirus Species 0.000 claims abstract description 4
• 241000709661 Enterovirus Species 0.000 claims abstract description 4
• 241000701076 Macacine alphaherpesvirus 1 Species 0.000 claims abstract description 4
• 208000000474 Poliomyelitis Diseases 0.000 claims abstract description 4
• 241000700647 Variola virus Species 0.000 claims abstract description 4
• 125000000217 alkyl group Chemical group 0.000 claims description 114
• -1 2H[ 1,2,3]triazol-4-yl Chemical group 0.000 claims description 99
• 125000003118 aryl group Chemical group 0.000 claims description 74
• 125000001072 heteroaryl group Chemical group 0.000 claims description 56
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 55
• 150000003839 salts Chemical class 0.000 claims description 48
• 125000003342 alkenyl group Chemical group 0.000 claims description 39
• 125000000304 alkynyl group Chemical group 0.000 claims description 37
• 229910052739 hydrogen Inorganic materials 0.000 claims description 37
• 125000003107 substituted aryl group Chemical group 0.000 claims description 35
• 125000002252 acyl group Chemical group 0.000 claims description 34
• 125000005017 substituted alkenyl group Chemical group 0.000 claims description 33
• 125000004426 substituted alkynyl group Chemical group 0.000 claims description 33
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 32
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 30
• 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 29
• 125000000623 heterocyclic group Chemical group 0.000 claims description 28
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 23
• 125000003545 alkoxy group Chemical group 0.000 claims description 22
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
• 229910052736 halogen Inorganic materials 0.000 claims description 20
• 150000002367 halogens Chemical class 0.000 claims description 20
• 229910003827 NRaRb Inorganic materials 0.000 claims description 19
• 229910052757 nitrogen Inorganic materials 0.000 claims description 19
• 229910052731 fluorine Inorganic materials 0.000 claims description 17
• 235000000346 sugar Nutrition 0.000 claims description 17
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 15
• 125000004122 cyclic group Chemical group 0.000 claims description 14
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 13
• 125000004429 atom Chemical group 0.000 claims description 13
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 13
• 125000005505 thiomorpholino group Chemical group 0.000 claims description 13
• 125000004432 carbon atom Chemical group C* 0.000 claims description 12
• 125000005842 heteroatom Chemical group 0.000 claims description 12
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 12
• IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 claims description 11
• 125000003282 alkyl amino group Chemical group 0.000 claims description 11
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 11
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
• HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 claims description 11
• 229960000329 ribavirin Drugs 0.000 claims description 11
• 125000004423 acyloxy group Chemical group 0.000 claims description 10
• 150000001413 amino acids Chemical class 0.000 claims description 10
• QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 10
• VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims description 10
• 239000001226 triphosphate Substances 0.000 claims description 10
• 125000004104 aryloxy group Chemical group 0.000 claims description 9
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
• 125000005041 acyloxyalkyl group Chemical group 0.000 claims description 8
• 125000000539 amino acid group Chemical group 0.000 claims description 8
• 125000002264 triphosphate group Chemical group [H]OP(=O)(O[H])OP(=O)(O[H])OP(=O)(O[H])O* 0.000 claims description 8
• 239000001177 diphosphate Substances 0.000 claims description 7
• 229910052740 iodine Inorganic materials 0.000 claims description 7
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
• 125000004055 thiomethyl group Chemical group [H]SC([H])([H])* 0.000 claims description 7
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
• 241000124008 Mammalia Species 0.000 claims description 6
• MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 6
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 6
• 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 6
• 239000003112 inhibitor Substances 0.000 claims description 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
• 125000004414 alkyl thio group Chemical group 0.000 claims description 5
• 239000003443 antiviral agent Substances 0.000 claims description 5
• 229910052794 bromium Inorganic materials 0.000 claims description 5
• 101150068479 chrb gene Proteins 0.000 claims description 5
• 125000005843 halogen group Chemical group 0.000 claims description 5
• 229910052701 rubidium Inorganic materials 0.000 claims description 5
• DLMDGLJCWXETIS-UHFFFAOYSA-N triazine-5-carboxylic acid Chemical compound OC(=O)C1=CN=NN=C1 DLMDGLJCWXETIS-UHFFFAOYSA-N 0.000 claims description 5
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
• 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 4
• IWUCXVSUMQZMFG-RGDLXGNYSA-N 1-[(2s,3s,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxamide Chemical compound N1=C(C(=O)N)N=CN1[C@@H]1[C@@H](O)[C@@H](O)[C@H](CO)O1 IWUCXVSUMQZMFG-RGDLXGNYSA-N 0.000 claims description 4
• JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 4
• CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 4
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
• 125000003835 nucleoside group Chemical group 0.000 claims description 4
• 229920006395 saturated elastomer Polymers 0.000 claims description 4
• 125000005415 substituted alkoxy group Chemical group 0.000 claims description 4
• 235000011178 triphosphate Nutrition 0.000 claims description 4
• NJYXSKVOTDPOAT-LMVFSUKVSA-N (2r,3r,4r)-2-fluoro-3,4,5-trihydroxypentanal Chemical group OC[C@@H](O)[C@@H](O)[C@@H](F)C=O NJYXSKVOTDPOAT-LMVFSUKVSA-N 0.000 claims description 3
• OECHUGCITYQGCY-YUMQZZPRSA-N (2s)-5-amino-2-[[(2s)-2,5-diaminopentanoyl]amino]pentanoic acid Chemical compound NCCC[C@H](N)C(=O)N[C@H](C(O)=O)CCCN OECHUGCITYQGCY-YUMQZZPRSA-N 0.000 claims description 3
• LFRDGHVRPSURMV-YFKPBYRVSA-N (4s)-4,5-dihydroxypentanal Chemical group OC[C@@H](O)CCC=O LFRDGHVRPSURMV-YFKPBYRVSA-N 0.000 claims description 3
• XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical compound N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 claims description 3
• OOUNPZOLTCEMSL-UHFFFAOYSA-N 2-(hydroxymethyl)-3-methyloxolane-3,4-diol Chemical compound CC1(O)C(O)COC1CO OOUNPZOLTCEMSL-UHFFFAOYSA-N 0.000 claims description 3
• ASJSAQIRZKANQN-CRCLSJGQSA-N 2-deoxy-D-ribose Chemical group OC[C@@H](O)[C@@H](O)CC=O ASJSAQIRZKANQN-CRCLSJGQSA-N 0.000 claims description 3
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 3
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
• PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 claims description 3
• HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 claims description 3
• PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical group OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 claims description 3
• PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Chemical group OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 claims description 3
• SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Chemical group OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims description 3
• 125000001246 bromo group Chemical group Br* 0.000 claims description 3
• 229910052799 carbon Inorganic materials 0.000 claims description 3
• 125000001153 fluoro group Chemical group F* 0.000 claims description 3
• UHCBBWUQDAVSMS-UHFFFAOYSA-N fluoroethane Chemical compound CCF UHCBBWUQDAVSMS-UHFFFAOYSA-N 0.000 claims description 3
• 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 3
• 229910052698 phosphorus Inorganic materials 0.000 claims description 3
• 239000011574 phosphorus Substances 0.000 claims description 3
• 125000000464 thioxo group Chemical group S=* 0.000 claims description 3
• UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 claims description 3
• OSBKZZCHLHZCDB-PBXRRBTRSA-N (2r,3r,4r)-2,3,4,5-tetrahydroxy-2-methylpentanal Chemical group O=C[C@@](O)(C)[C@H](O)[C@H](O)CO OSBKZZCHLHZCDB-PBXRRBTRSA-N 0.000 claims description 2
• KDKMTIRSYIHSTB-MROZADKFSA-N (2r,3r,4r)-2,3,4,5-tetrahydroxypentanethial Chemical group OC[C@@H](O)[C@@H](O)[C@@H](O)C=S KDKMTIRSYIHSTB-MROZADKFSA-N 0.000 claims description 2
• SQXRWAVEVYDDBF-LMVFSUKVSA-N (2r,3r,4r)-2-fluoro-3,4,5-trihydroxypentanethial Chemical group OC[C@@H](O)[C@@H](O)[C@@H](F)C=S SQXRWAVEVYDDBF-LMVFSUKVSA-N 0.000 claims description 2
• NJYXSKVOTDPOAT-WDCZJNDASA-N (2s,3r,4r)-2-fluoro-3,4,5-trihydroxypentanal Chemical group OC[C@@H](O)[C@@H](O)[C@H](F)C=O NJYXSKVOTDPOAT-WDCZJNDASA-N 0.000 claims description 2
• PYMIDWYUQAHNQK-WHFBIAKZSA-N (2s,4s)-2-fluoro-4,5-dihydroxypentanal Chemical group OC[C@@H](O)C[C@H](F)C=O PYMIDWYUQAHNQK-WHFBIAKZSA-N 0.000 claims description 2
• BKNVTPUCZNUJMP-WHFBIAKZSA-N (2s,4s)-2-fluoro-4,5-dihydroxypentanethial Chemical compound OC[C@@H](O)C[C@H](F)C=S BKNVTPUCZNUJMP-WHFBIAKZSA-N 0.000 claims description 2
• ANFWGLPWDSXJEH-CRCLSJGQSA-N (3s,4r)-3,4,5-trihydroxypentanethial Chemical group OC[C@@H](O)[C@@H](O)CC=S ANFWGLPWDSXJEH-CRCLSJGQSA-N 0.000 claims description 2
• MJMJUKHABPJQGX-CRCLSJGQSA-N (3s,4r)-3-fluoro-4,5-dihydroxypentanal Chemical group OC[C@@H](O)[C@@H](F)CC=O MJMJUKHABPJQGX-CRCLSJGQSA-N 0.000 claims description 2
• JBFNVLCLNHQXCH-CRCLSJGQSA-N (3s,4r)-3-fluoro-4,5-dihydroxypentanethial Chemical compound OC[C@@H](O)[C@@H](F)CC=S JBFNVLCLNHQXCH-CRCLSJGQSA-N 0.000 claims description 2
• XFBDCPQESJYXPC-YFKPBYRVSA-N (4s)-4,5-dihydroxypentanethial Chemical compound OC[C@@H](O)CCC=S XFBDCPQESJYXPC-YFKPBYRVSA-N 0.000 claims description 2
• UMZKOJVNUVDHED-UHFFFAOYSA-N 1,2,4-triazine-5-carboximidamide Chemical compound NC(=N)C1=CN=NC=N1 UMZKOJVNUVDHED-UHFFFAOYSA-N 0.000 claims description 2
• UADBLZFWTJHOJC-UHFFFAOYSA-N 2-(hydroxymethyl)cyclopentan-1-ol Chemical group OCC1CCCC1O UADBLZFWTJHOJC-UHFFFAOYSA-N 0.000 claims description 2
• OIEIKVCEXBMETK-BYPYZUCNSA-N 2-[(1s)-1,2-dihydroxyethoxy]acetaldehyde Chemical compound OC[C@@H](O)OCC=O OIEIKVCEXBMETK-BYPYZUCNSA-N 0.000 claims description 2
• VQKBTEBRZHBIGE-BYPYZUCNSA-N 2-[(1s)-1,2-dihydroxyethyl]sulfanylacetaldehyde Chemical compound OC[C@@H](O)SCC=O VQKBTEBRZHBIGE-BYPYZUCNSA-N 0.000 claims description 2
• NTSRIMQXXYCAGF-UHFFFAOYSA-N 2-fluoro-5-(hydroxymethyl)cyclopentan-1-ol Chemical group OCC1CCC(F)C1O NTSRIMQXXYCAGF-UHFFFAOYSA-N 0.000 claims description 2
• DITIGNGDSVRJFX-UHFFFAOYSA-N 3-(hydroxymethyl)-4-methylidenecyclopentane-1,2-diol Chemical group OCC1C(O)C(O)CC1=C DITIGNGDSVRJFX-UHFFFAOYSA-N 0.000 claims description 2
• DWROYQTVCUQGJR-UHFFFAOYSA-N 3-(hydroxymethyl)cyclopent-3-ene-1,2-diol Chemical group OCC1=CCC(O)C1O DWROYQTVCUQGJR-UHFFFAOYSA-N 0.000 claims description 2
• MZQHDBUGKAFSOC-UHFFFAOYSA-N 3-(hydroxymethyl)cyclopentane-1,2-diol Chemical group OCC1CCC(O)C1O MZQHDBUGKAFSOC-UHFFFAOYSA-N 0.000 claims description 2
• WQSIEHZPHQVPFS-UHFFFAOYSA-N 3-fluoro-4-(hydroxymethyl)pyrrolidin-2-ol Chemical compound OCC1CNC(O)C1F WQSIEHZPHQVPFS-UHFFFAOYSA-N 0.000 claims description 2
• BORAVSBFYTYKOE-UHFFFAOYSA-N 4-(hydroxymethyl)cyclopenten-1-ol Chemical group OCC1CC=C(O)C1 BORAVSBFYTYKOE-UHFFFAOYSA-N 0.000 claims description 2
• UKDQIWLEEJYIDQ-UHFFFAOYSA-N 4-(hydroxymethyl)pyrrolidine-2,3-diol Chemical group OCC1CNC(O)C1O UKDQIWLEEJYIDQ-UHFFFAOYSA-N 0.000 claims description 2
• 101100294106 Caenorhabditis elegans nhr-3 gene Proteins 0.000 claims description 2
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
• 229930010555 Inosine Natural products 0.000 claims description 2
• UGQMRVRMYYASKQ-KQYNXXCUSA-N Inosine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC=NC(O)=C2N=C1 UGQMRVRMYYASKQ-KQYNXXCUSA-N 0.000 claims description 2
• 102000012479 Serine Proteases Human genes 0.000 claims description 2
• 108010022999 Serine Proteases Proteins 0.000 claims description 2
• 108010078233 Thymalfasin Proteins 0.000 claims description 2
• 102400000800 Thymosin alpha-1 Human genes 0.000 claims description 2
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
• LMYOLOWXQDLHKQ-UHFFFAOYSA-N cyclopent-2-en-1-ylmethanol Chemical group OCC1CCC=C1 LMYOLOWXQDLHKQ-UHFFFAOYSA-N 0.000 claims description 2
• ISQVBYGGNVVVHB-UHFFFAOYSA-N cyclopentylmethanol Chemical group OCC1CCCC1 ISQVBYGGNVVVHB-UHFFFAOYSA-N 0.000 claims description 2
• RGAPPBGFFPGONM-CRCLSJGQSA-N diazonio-[(2s,3s)-1,2-dihydroxy-5-sulfanylidenepentan-3-yl]azanide Chemical compound OC[C@@H](O)[C@H](CC=S)N=[N+]=[N-] RGAPPBGFFPGONM-CRCLSJGQSA-N 0.000 claims description 2
• 229960003786 inosine Drugs 0.000 claims description 2
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
• 150000004712 monophosphates Chemical group 0.000 claims description 2
• QOTUIIJRVXKSJU-UHFFFAOYSA-N pyrrolidin-3-ylmethanol Chemical group OCC1CCNC1 QOTUIIJRVXKSJU-UHFFFAOYSA-N 0.000 claims description 2
• 125000000548 ribosyl group Chemical group C1([C@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims description 2
• NHKZSTHOYNWEEZ-AFCXAGJDSA-N taribavirin Chemical compound N1=C(C(=N)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 NHKZSTHOYNWEEZ-AFCXAGJDSA-N 0.000 claims description 2
• 229950006081 taribavirin Drugs 0.000 claims description 2
• NZVYCXVTEHPMHE-ZSUJOUNUSA-N thymalfasin Chemical compound CC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(N)=O)C(O)=O NZVYCXVTEHPMHE-ZSUJOUNUSA-N 0.000 claims description 2
• 229960004231 thymalfasin Drugs 0.000 claims description 2
• LKIQJYQAFUOZPN-UHFFFAOYSA-N triazine-5-carbonitrile Chemical compound N#CC1=CN=NN=C1 LKIQJYQAFUOZPN-UHFFFAOYSA-N 0.000 claims description 2
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
• 229920002554 vinyl polymer Polymers 0.000 claims description 2
• 125000001589 carboacyl group Chemical group 0.000 claims 4
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
• SQXRWAVEVYDDBF-WDCZJNDASA-N (2s,3r,4r)-2-fluoro-3,4,5-trihydroxypentanethial Chemical compound OC[C@@H](O)[C@@H](O)[C@H](F)C=S SQXRWAVEVYDDBF-WDCZJNDASA-N 0.000 claims 1
• IJIHMDVMMUTJEJ-UHFFFAOYSA-N 1,2,4-triazine-5-carboxamide Chemical compound NC(=O)C1=CN=NC=N1 IJIHMDVMMUTJEJ-UHFFFAOYSA-N 0.000 claims 1
• NGWKEVMCTIVMBA-UHFFFAOYSA-N 2-fluoro-4-(hydroxymethyl)pyrrolidin-3-ol Chemical compound OCC1CNC(F)C1O NGWKEVMCTIVMBA-UHFFFAOYSA-N 0.000 claims 1
• SVMRIWUVQVPFTQ-UHFFFAOYSA-N 2h-pyrrolo[1,2-d][1,2,4]triazin-1-one Chemical compound O=C1NN=CN2C=CC=C12 SVMRIWUVQVPFTQ-UHFFFAOYSA-N 0.000 claims 1
• 229940124683 HCV polymerase inhibitor Drugs 0.000 claims 1
• GAADRFVRUBFCML-UHFFFAOYSA-N [2-(hydroxymethyl)cyclobutyl]methanol Chemical compound OCC1CCC1CO GAADRFVRUBFCML-UHFFFAOYSA-N 0.000 claims 1
• CCRXJMDIIXJVIC-CRCLSJGQSA-N diazonio-[(2s,3s)-1,2-dihydroxy-5-oxopentan-3-yl]azanide Chemical compound OC[C@@H](O)[C@H](CC=O)N=[N+]=[N-] CCRXJMDIIXJVIC-CRCLSJGQSA-N 0.000 claims 1
• 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 claims 1
• CPRRHERYRRXBRZ-SRVKXCTJSA-N methyl n-[(2s)-1-[[(2s)-1-hydroxy-3-[(3s)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CO)C[C@@H]1CCNC1=O CPRRHERYRRXBRZ-SRVKXCTJSA-N 0.000 claims 1
• 125000004304 oxazol-5-yl group Chemical group O1C=NC=C1* 0.000 claims 1
• 239000000137 peptide hydrolase inhibitor Substances 0.000 claims 1
• 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 173
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