CA3036428A1 - Antiviral compounds - Google Patents
Antiviral compounds Download PDFInfo
- Publication number
- CA3036428A1 CA3036428A1 CA3036428A CA3036428A CA3036428A1 CA 3036428 A1 CA3036428 A1 CA 3036428A1 CA 3036428 A CA3036428 A CA 3036428A CA 3036428 A CA3036428 A CA 3036428A CA 3036428 A1 CA3036428 A1 CA 3036428A1
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- CA
- Canada
- Prior art keywords
- nmr
- purity
- nrere
- mhz
- synthesized
- 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.)
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 318
- 230000000840 anti-viral effect Effects 0.000 title description 4
- -1 diastereomers Chemical class 0.000 claims description 128
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 66
- 125000001072 heteroaryl group Chemical group 0.000 claims description 48
- 239000000203 mixture Substances 0.000 claims description 46
- 150000003839 salts Chemical class 0.000 claims description 41
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 29
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 26
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 25
- 125000001424 substituent group Chemical group 0.000 claims description 23
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 21
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 21
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 20
- 150000004677 hydrates Chemical class 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 10
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 125000004043 oxo group Chemical group O=* 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
- 239000013543 active substance Substances 0.000 claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 206010028980 Neoplasm Diseases 0.000 claims description 3
- 208000008589 Obesity Diseases 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 235000020824 obesity Nutrition 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- 208000035473 Communicable disease Diseases 0.000 claims description 2
- 201000011510 cancer Diseases 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
- 208000005155 Picornaviridae Infections Diseases 0.000 claims 1
- 101000595800 Homo sapiens Phospholipase A and acyltransferase 3 Proteins 0.000 abstract description 7
- 208000036142 Viral infection Diseases 0.000 abstract description 7
- 230000009385 viral infection Effects 0.000 abstract description 7
- 102100036066 Phospholipase A and acyltransferase 3 Human genes 0.000 abstract description 6
- 201000010099 disease Diseases 0.000 abstract description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 5
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 238000000034 method Methods 0.000 description 460
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 332
- 238000005160 1H NMR spectroscopy Methods 0.000 description 308
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 223
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 222
- 238000000746 purification Methods 0.000 description 219
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 190
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 142
- 239000003921 oil Substances 0.000 description 118
- 235000019198 oils Nutrition 0.000 description 118
- 239000012071 phase Substances 0.000 description 114
- 238000003818 flash chromatography Methods 0.000 description 113
- 239000000377 silicon dioxide Substances 0.000 description 111
- 239000007787 solid Substances 0.000 description 100
- XZOWIJDBQIHMFC-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O.CCCC(N)=O XZOWIJDBQIHMFC-UHFFFAOYSA-N 0.000 description 71
- 239000003643 water by type Substances 0.000 description 64
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 51
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 51
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 46
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 44
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 40
- 239000000243 solution Substances 0.000 description 32
- 238000001953 recrystallisation Methods 0.000 description 30
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 29
- 238000010828 elution Methods 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- 238000001665 trituration Methods 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 24
- 238000002347 injection Methods 0.000 description 23
- 239000007924 injection Substances 0.000 description 23
- 238000002211 ultraviolet spectrum Methods 0.000 description 22
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 21
- 230000002378 acidificating effect Effects 0.000 description 21
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 20
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 20
- 235000019253 formic acid Nutrition 0.000 description 20
- 239000000843 powder Substances 0.000 description 20
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 18
- 229910052938 sodium sulfate Inorganic materials 0.000 description 18
- 235000011152 sodium sulphate Nutrition 0.000 description 18
- 125000000217 alkyl group Chemical group 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 17
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 15
- 125000004432 carbon atom Chemical class C* 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- 239000012044 organic layer Substances 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 229920006395 saturated elastomer Polymers 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 11
- 238000001819 mass spectrum Methods 0.000 description 11
- 238000005070 sampling Methods 0.000 description 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 11
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 239000003480 eluent Substances 0.000 description 10
- 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 10
- HLEKYJVHEBHTMR-UHFFFAOYSA-N pentanamide Chemical compound CCCCC(N)=O.CCCCC(N)=O HLEKYJVHEBHTMR-UHFFFAOYSA-N 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 230000002441 reversible effect Effects 0.000 description 10
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- BEPOKULTVBNNKT-UHFFFAOYSA-N N-(cyclohexylmethyl)-3-methyloxirane-2-carboxamide Chemical compound C1(CCCCC1)CNC(=O)C1OC1C BEPOKULTVBNNKT-UHFFFAOYSA-N 0.000 description 9
- 241000700605 Viruses Species 0.000 description 9
- 125000004429 atom Chemical group 0.000 description 9
- 125000000753 cycloalkyl group Chemical group 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
- FMAZQSYXRGRESX-UHFFFAOYSA-N Glycidamide Chemical compound NC(=O)C1CO1 FMAZQSYXRGRESX-UHFFFAOYSA-N 0.000 description 8
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 235000011114 ammonium hydroxide Nutrition 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- 125000002619 bicyclic group Chemical group 0.000 description 8
- NYTAJBJUEATPED-UHFFFAOYSA-N C(C)(C)NC(=O)C1OC1C Chemical compound C(C)(C)NC(=O)C1OC1C NYTAJBJUEATPED-UHFFFAOYSA-N 0.000 description 7
- BAECEWNJOANEAK-UHFFFAOYSA-N N-(cyclopropylmethyl)-3-(2-methylpropyl)oxirane-2-carboxamide Chemical compound C1(CC1)CNC(=O)C1OC1CC(C)C BAECEWNJOANEAK-UHFFFAOYSA-N 0.000 description 7
- 239000000908 ammonium hydroxide Substances 0.000 description 7
- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 239000013058 crude material Substances 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 150000002430 hydrocarbons Chemical group 0.000 description 7
- 238000004808 supercritical fluid chromatography Methods 0.000 description 7
- NQQRXZOPZBKCNF-NSCUHMNNSA-N (e)-but-2-enamide Chemical compound C\C=C\C(N)=O NQQRXZOPZBKCNF-NSCUHMNNSA-N 0.000 description 6
- LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 6
- 241000709661 Enterovirus Species 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- PCBIWZJNPLHYGL-UHFFFAOYSA-N N-(cyclopropylmethyl)-3-propyloxirane-2-carboxamide Chemical compound C1(CC1)CNC(=O)C1OC1CCC PCBIWZJNPLHYGL-UHFFFAOYSA-N 0.000 description 6
- 241000709664 Picornaviridae Species 0.000 description 6
- 238000010640 amide synthesis reaction Methods 0.000 description 6
- 150000002118 epoxides Chemical class 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 238000005342 ion exchange Methods 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Inorganic materials [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium;hydroxide;hydrate Chemical compound [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 6
- DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 5
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 5
- 239000007821 HATU Substances 0.000 description 5
- UTGXVVDJGWARQB-UHFFFAOYSA-N N-(cyclohexylmethyl)-3-ethyloxirane-2-carboxamide Chemical compound C1(CCCCC1)CNC(=O)C1OC1CC UTGXVVDJGWARQB-UHFFFAOYSA-N 0.000 description 5
- HEJBYYPXMRTPGR-UHFFFAOYSA-N N-(cyclopropylmethyl)-3-methyloxirane-2-carboxamide Chemical compound C1(CC1)CNC(=O)C1OC1C HEJBYYPXMRTPGR-UHFFFAOYSA-N 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 125000000304 alkynyl group Chemical group 0.000 description 5
- 235000012538 ammonium bicarbonate Nutrition 0.000 description 5
- 239000001099 ammonium carbonate Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 5
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 125000002950 monocyclic group Chemical group 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
- PAQZWJGSJMLPMG-UHFFFAOYSA-N 2,4,6-tripropyl-1,3,5,2$l^{5},4$l^{5},6$l^{5}-trioxatriphosphinane 2,4,6-trioxide Chemical compound CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1 PAQZWJGSJMLPMG-UHFFFAOYSA-N 0.000 description 4
- HRJTXSXEZVGCGU-UHFFFAOYSA-N 3-cyclopropyl-N-(cyclopropylmethyl)oxirane-2-carboxamide Chemical compound C1(CC1)C1C(O1)C(=O)NCC1CC1 HRJTXSXEZVGCGU-UHFFFAOYSA-N 0.000 description 4
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 241000991587 Enterovirus C Species 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 description 4
- 238000004296 chiral HPLC Methods 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- IGSKHXTUVXSOMB-UHFFFAOYSA-N cyclopropylmethanamine Chemical compound NCC1CC1 IGSKHXTUVXSOMB-UHFFFAOYSA-N 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- ALBYIUDWACNRRB-UHFFFAOYSA-N hexanamide Chemical compound CCCCCC(N)=O ALBYIUDWACNRRB-UHFFFAOYSA-N 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- 235000010446 mineral oil Nutrition 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Substances [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 4
- PLWMGMCBGZYSHL-AATRIKPKSA-N (E)-3-cyclopropyl-N-(cyclopropylmethyl)prop-2-enamide Chemical compound C1(CC1)/C=C/C(=O)NCC1CC1 PLWMGMCBGZYSHL-AATRIKPKSA-N 0.000 description 3
- DBGZGINMCMTNRO-QHHAFSJGSA-N (E)-N-(cyclohexylmethyl)but-2-enamide Chemical compound C1(CCCCC1)CNC(\C=C\C)=O DBGZGINMCMTNRO-QHHAFSJGSA-N 0.000 description 3
- YNVIDWBXYIJJOS-YCRREMRBSA-N (E)-N-(cyclohexylmethyl)pent-2-enamide Chemical compound C1(CCCCC1)CNC(\C=C\CC)=O YNVIDWBXYIJJOS-YCRREMRBSA-N 0.000 description 3
- DHMNPKGDYKWZEA-ONEGZZNKSA-N (E)-N-(cyclopropylmethyl)-3-(oxan-4-yl)prop-2-enamide Chemical compound C1(CC1)CNC(\C=C\C1CCOCC1)=O DHMNPKGDYKWZEA-ONEGZZNKSA-N 0.000 description 3
- SBHZTEYHXIPFEB-DUXPYHPUSA-N (E)-N-(cyclopropylmethyl)-5-methoxypent-2-enamide Chemical compound C1(CC1)CNC(\C=C\CCOC)=O SBHZTEYHXIPFEB-DUXPYHPUSA-N 0.000 description 3
- JKNLIHRSRMGWQX-WEVVVXLNSA-N (E)-N-(cyclopropylmethyl)-5-phenylpent-2-enamide Chemical compound C1(CC1)CNC(\C=C\CCC1=CC=CC=C1)=O JKNLIHRSRMGWQX-WEVVVXLNSA-N 0.000 description 3
- ONVORYYNCOYBEH-SNAWJCMRSA-N (E)-N-(cyclopropylmethyl)hex-2-enamide Chemical compound C1(CC1)CNC(\C=C\CCC)=O ONVORYYNCOYBEH-SNAWJCMRSA-N 0.000 description 3
- WRFLTLVXCKWWBI-SNAWJCMRSA-N (e)-n-(2-methylpropyl)but-2-enamide Chemical compound C\C=C\C(=O)NCC(C)C WRFLTLVXCKWWBI-SNAWJCMRSA-N 0.000 description 3
- PMYOYDPRILKMKB-SNAWJCMRSA-N (e)-n-propan-2-ylbut-2-enamide Chemical compound C\C=C\C(=O)NC(C)C PMYOYDPRILKMKB-SNAWJCMRSA-N 0.000 description 3
- LHSNWZRMVCJRKH-UHFFFAOYSA-N 2-hydroxy-3-(2-methoxyanilino)butanamide Chemical compound OC(C(=O)N)C(C)NC1=C(C=CC=C1)OC LHSNWZRMVCJRKH-UHFFFAOYSA-N 0.000 description 3
- FCDWUGOEWNFAOK-UHFFFAOYSA-N 3-(2,2-dimethylpropylamino)-2-hydroxy-N-(2-methylpropyl)butanamide Chemical compound CC(CNC(C(C(=O)NCC(C)C)O)C)(C)C FCDWUGOEWNFAOK-UHFFFAOYSA-N 0.000 description 3
- AEGVLQYCTASNHG-UHFFFAOYSA-N 3-(2,2-dimethylpropylamino)-2-hydroxy-N-propan-2-ylbutanamide Chemical compound CC(CNC(C(C(=O)NC(C)C)O)C)(C)C AEGVLQYCTASNHG-UHFFFAOYSA-N 0.000 description 3
- BDRMIESVQVGXJP-UHFFFAOYSA-N 3-(benzylamino)-N-(cyclopropylmethyl)-2-hydroxy-5-methoxypentanamide Chemical compound C(C1=CC=CC=C1)NC(C(C(=O)NCC1CC1)O)CCOC BDRMIESVQVGXJP-UHFFFAOYSA-N 0.000 description 3
- JXUBGHBMYSYIRJ-UHFFFAOYSA-N 3-(cyclohexylamino)-N-(cyclohexylmethyl)-2-hydroxypentanamide Chemical compound C1(CCCCC1)NC(C(C(=O)NCC1CCCCC1)O)CC JXUBGHBMYSYIRJ-UHFFFAOYSA-N 0.000 description 3
- LKSXPYPFMQVOPK-UHFFFAOYSA-N 3-[cyclohexyl(formyl)amino]-2-hydroxy-N-(2-methylpropyl)butanamide Chemical compound C1(CCCCC1)N(C=O)C(C(C(=O)NCC(C)C)O)C LKSXPYPFMQVOPK-UHFFFAOYSA-N 0.000 description 3
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000711549 Hepacivirus C Species 0.000 description 3
- 241000282412 Homo Species 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- GDGRZJHQBDJPTQ-UHFFFAOYSA-N N-(cyclopropylmethyl)-3-(2,2-dimethylpropylamino)-2-hydroxy-4-methylpentanamide Chemical compound C1(CC1)CNC(C(C(C(C)C)NCC(C)(C)C)O)=O GDGRZJHQBDJPTQ-UHFFFAOYSA-N 0.000 description 3
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- 230000005180 public health Effects 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- HNJBEVLQSNELDL-YZRHJBSPSA-N pyrrolidin-2-one Chemical group O=C1CC[14CH2]N1 HNJBEVLQSNELDL-YZRHJBSPSA-N 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 150000003870 salicylic acids Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000012163 sequencing technique Methods 0.000 description 1
- 150000003384 small molecules Chemical class 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
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- WGRULTCAYDOGQK-UHFFFAOYSA-M sodium;sodium;hydroxide Chemical compound [OH-].[Na].[Na+] WGRULTCAYDOGQK-UHFFFAOYSA-M 0.000 description 1
- LZCVVMQABORALM-UHFFFAOYSA-N spiro[2.5]octyl Chemical group [CH]1CC11CCCCC1 LZCVVMQABORALM-UHFFFAOYSA-N 0.000 description 1
- LMUMMJCCZMWLEN-UHFFFAOYSA-N spiro[3.3]heptyl Chemical group [CH]1CCC11CCC1 LMUMMJCCZMWLEN-UHFFFAOYSA-N 0.000 description 1
- CCOIJUDZGUXWEH-UHFFFAOYSA-N spiro[4.5]dec-2-ene Chemical compound C1C=CCC11CCCCC1 CCOIJUDZGUXWEH-UHFFFAOYSA-N 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
- PHCBRBWANGJMHS-UHFFFAOYSA-J tetrasodium;disulfate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O PHCBRBWANGJMHS-UHFFFAOYSA-J 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- YIYBQIKDCADOSF-ONEGZZNKSA-N trans-pent-2-enoic acid Chemical compound CC\C=C\C(O)=O YIYBQIKDCADOSF-ONEGZZNKSA-N 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 238000004704 ultra performance liquid chromatography Methods 0.000 description 1
- 241000701161 unidentified adenovirus Species 0.000 description 1
- 241001529453 unidentified herpesvirus Species 0.000 description 1
- 241000712461 unidentified influenza virus Species 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 210000000605 viral structure Anatomy 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/72—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms
- C07C235/74—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of a saturated carbon skeleton
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- 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
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/22—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
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- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/24—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a ring other than a six-membered aromatic ring
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- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/03—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms
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- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/03—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C311/06—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms to acyclic carbon atoms of hydrocarbon radicals substituted by carboxyl groups
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- C07C311/10—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of a saturated carbon skeleton containing rings
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- C07C311/12—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings
- C07C311/13—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings the carbon skeleton containing six-membered aromatic rings
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- C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
- C07C311/19—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
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- C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
- C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
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- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
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- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
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- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
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- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
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- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
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- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/12—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D261/18—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Molecular Biology (AREA)
- Public Health (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Furan Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| EP16188559 | 2016-09-13 | ||
| EP16188559.5 | 2016-09-13 | ||
| PCT/EP2017/072880 WO2018050631A1 (en) | 2016-09-13 | 2017-09-12 | Antiviral compounds |
Publications (1)
| Publication Number | Publication Date |
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| CA3036428A1 true CA3036428A1 (en) | 2018-03-22 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| CA3036428A Pending CA3036428A1 (en) | 2016-09-13 | 2017-09-12 | Antiviral compounds |
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| EP (1) | EP3512836A1 (enExample) |
| JP (2) | JP2019533007A (enExample) |
| CN (1) | CN110062753A (enExample) |
| CA (1) | CA3036428A1 (enExample) |
| WO (1) | WO2018050631A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110062753A (zh) * | 2016-09-13 | 2019-07-26 | 哈普洛根有限责任公司 | 抗病毒化合物 |
| CN111303005B (zh) * | 2020-03-24 | 2023-09-08 | 乌海青石化学有限公司 | 含邻苯二甲酰亚胺结构的偶合组分及其制备方法和应用 |
| WO2024151465A1 (en) * | 2023-01-09 | 2024-07-18 | Merck Sharp & Dohme Llc | Protease inhibitors for treating or preventing coronavirus infection |
| WO2025171103A1 (en) * | 2024-02-08 | 2025-08-14 | Luxvitae Therapeutics Inc. | Amino acid derivatives and method of making the same |
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| JPS5681543A (en) * | 1979-10-10 | 1981-07-03 | Ciba Geigy Ag | Manufacture of diether |
| JPH06273417A (ja) * | 1993-01-20 | 1994-09-30 | Ono Pharmaceut Co Ltd | メバロン酸に対する抗体、および該抗体を用いるメバロン酸の定量法 |
| RU2054415C1 (ru) * | 1994-03-02 | 1996-02-20 | Товарищество с ограниченной ответственностью "Пант" | Кетопантотенат кальция, обладающий ацетилирующей активностью d-пантотената кальция |
| RU2054000C1 (ru) * | 1994-03-02 | 1996-02-10 | Товарищество с ограниченной ответственностью "Пант" | Кетопантенол, обладающий ацетилирующей активностью d-пантотената кальция |
| JP2002514192A (ja) * | 1996-11-13 | 2002-05-14 | セフアロン・インコーポレーテツド | ベンゾチアゾおよび関連の複素環基を含有するシステインおよびセリンプロテアーゼ阻害剤 |
| US6103720A (en) * | 1996-12-11 | 2000-08-15 | Basf Aktiengesellschaft | Ketobenzamides as calpain inhibitors |
| JP3892187B2 (ja) * | 1998-11-12 | 2007-03-14 | 生化学工業株式会社 | 環状アミド誘導体 |
| EP1206484B1 (en) * | 1999-08-04 | 2004-10-06 | Agouron Pharmaceuticals, Inc. | Antipicornaviral compounds and compositions, their pharmaceutical uses, and materials for their synthesis |
| US20030045710A1 (en) * | 2000-04-06 | 2003-03-06 | Bruice Thomas C. | Methods for identifying, obtaining and using new polyketide compounds |
| EP1343807B1 (en) * | 2000-12-12 | 2009-04-29 | Schering Corporation | Diaryl peptides as ns3-serine protease inhibitors of hepatits c virus |
| US20020177594A1 (en) * | 2001-03-14 | 2002-11-28 | Curtin Michael L. | Inhibitors of histone deacetylase |
| CA2709566A1 (en) * | 2007-12-17 | 2009-06-25 | Gliamed, Inc. | Stem-like cells and method for reprogramming adult mammalian somatic cells |
| US8236798B2 (en) * | 2009-05-07 | 2012-08-07 | Abbott Gmbh & Co. Kg | Carboxamide compounds and their use as calpain inhibitors |
| MX344373B (es) * | 2010-01-27 | 2016-12-13 | Ab Pharma Ltd * | Compuestos policiclicos heterociclicos se puede utilizar como inhibidores eficaces para virus de la hepatitis c. |
| WO2011160043A2 (en) | 2010-06-18 | 2011-12-22 | Whitehead Institute For Biomedical Research | Pla2g16 as a target for antiviral compounds |
| US20140249073A1 (en) * | 2011-05-27 | 2014-09-04 | Rqx Pharmaceuticals, Inc | Broad spectrum antibiotics |
| CA2850003C (en) | 2011-09-27 | 2020-01-07 | Kansas State University Research Foundation | Broad-spectrum antivirals against 3c or 3c-like proteases of picornavirus-like supercluster: picornaviruses, caliciviruses and coronaviruses |
| US20140256698A1 (en) * | 2013-03-11 | 2014-09-11 | Virobay, Inc. | Cathepsin inhibitors |
| GB201305750D0 (en) | 2013-03-28 | 2013-05-15 | Syngenta Ltd | Herbicidal Compounds |
| SG11201608242XA (en) | 2014-04-04 | 2016-10-28 | Syros Pharmaceuticals Inc | Inhibitors of cyclin-dependent kinase 7 (cdk7) |
| CN110062753A (zh) * | 2016-09-13 | 2019-07-26 | 哈普洛根有限责任公司 | 抗病毒化合物 |
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2017
- 2017-09-12 CN CN201780069960.5A patent/CN110062753A/zh active Pending
- 2017-09-12 CA CA3036428A patent/CA3036428A1/en active Pending
- 2017-09-12 US US16/333,159 patent/US11091428B2/en active Active
- 2017-09-12 EP EP17771706.3A patent/EP3512836A1/en not_active Withdrawn
- 2017-09-12 JP JP2019535971A patent/JP2019533007A/ja active Pending
- 2017-09-12 WO PCT/EP2017/072880 patent/WO2018050631A1/en not_active Ceased
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2021
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2022
- 2022-06-29 JP JP2022104373A patent/JP2022137120A/ja active Pending
Also Published As
| Publication number | Publication date |
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| US20220356148A1 (en) | 2022-11-10 |
| JP2022137120A (ja) | 2022-09-21 |
| US11091428B2 (en) | 2021-08-17 |
| CN110062753A (zh) | 2019-07-26 |
| WO2018050631A1 (en) | 2018-03-22 |
| EP3512836A1 (en) | 2019-07-24 |
| JP2019533007A (ja) | 2019-11-14 |
| US20190225575A1 (en) | 2019-07-25 |
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