CA3081423A1 - Antibacterial compounds - Google Patents
Antibacterial compounds Download PDFInfo
- Publication number
- CA3081423A1 CA3081423A1 CA3081423A CA3081423A CA3081423A1 CA 3081423 A1 CA3081423 A1 CA 3081423A1 CA 3081423 A CA3081423 A CA 3081423A CA 3081423 A CA3081423 A CA 3081423A CA 3081423 A1 CA3081423 A1 CA 3081423A1
- Authority
- CA
- Canada
- Prior art keywords
- 4alkyl
- group
- phenyl
- optionally substituted
- membered heteroaryl
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 246
- 230000000844 anti-bacterial effect Effects 0.000 title description 15
- 239000000203 mixture Substances 0.000 claims abstract description 82
- 238000011282 treatment Methods 0.000 claims abstract description 36
- 238000000034 method Methods 0.000 claims abstract description 33
- 241000588921 Enterobacteriaceae Species 0.000 claims abstract description 28
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 26
- 208000015181 infectious disease Diseases 0.000 claims abstract description 24
- 201000010099 disease Diseases 0.000 claims abstract description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 452
- 125000001424 substituent group Chemical group 0.000 claims description 281
- 239000001257 hydrogen Substances 0.000 claims description 247
- 229910052739 hydrogen Inorganic materials 0.000 claims description 247
- 150000002367 halogens Chemical class 0.000 claims description 228
- 229910052736 halogen Inorganic materials 0.000 claims description 227
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 204
- 150000002431 hydrogen Chemical class 0.000 claims description 174
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 157
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 146
- -1 -CH2NR5R6 Chemical group 0.000 claims description 139
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 127
- 125000004076 pyridyl group Chemical group 0.000 claims description 119
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 110
- 150000003839 salts Chemical class 0.000 claims description 108
- 150000002148 esters Chemical class 0.000 claims description 100
- 239000012453 solvate Substances 0.000 claims description 97
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 81
- 150000001413 amino acids Chemical class 0.000 claims description 78
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 77
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 59
- 125000002619 bicyclic group Chemical group 0.000 claims description 57
- 125000002950 monocyclic group Chemical group 0.000 claims description 53
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 45
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 44
- 125000000623 heterocyclic group Chemical group 0.000 claims description 43
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 43
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 39
- 229910052731 fluorine Inorganic materials 0.000 claims description 32
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 31
- 229910052757 nitrogen Inorganic materials 0.000 claims description 31
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 29
- 239000008194 pharmaceutical composition Substances 0.000 claims description 27
- 239000003814 drug Substances 0.000 claims description 25
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 21
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- 125000004122 cyclic group Chemical group 0.000 claims description 14
- 101100134922 Gallus gallus COR5 gene Proteins 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 101100294106 Caenorhabditis elegans nhr-3 gene Proteins 0.000 claims description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
- 125000003277 amino group Chemical group 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 238000011321 prophylaxis Methods 0.000 claims description 8
- 239000003937 drug carrier Substances 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical group OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 6
- 125000006164 6-membered heteroaryl group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 238000002560 therapeutic procedure Methods 0.000 claims description 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 15
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 8
- 208000035143 Bacterial infection Diseases 0.000 abstract description 9
- 208000022362 bacterial infectious disease Diseases 0.000 abstract description 6
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 196
- 238000005160 1H NMR spectroscopy Methods 0.000 description 140
- 239000011541 reaction mixture Substances 0.000 description 130
- 239000000243 solution Substances 0.000 description 93
- 230000002829 reductive effect Effects 0.000 description 92
- 238000006243 chemical reaction Methods 0.000 description 81
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 80
- 239000007787 solid Substances 0.000 description 73
- 125000005605 benzo group Chemical group 0.000 description 70
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 63
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 62
- 229910001868 water Inorganic materials 0.000 description 62
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 56
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 56
- 239000007832 Na2SO4 Substances 0.000 description 55
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 55
- 229910052938 sodium sulfate Inorganic materials 0.000 description 55
- 235000011152 sodium sulphate Nutrition 0.000 description 55
- 150000001412 amines Chemical class 0.000 description 53
- 239000003795 chemical substances by application Substances 0.000 description 50
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 44
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 44
- 239000000460 chlorine Substances 0.000 description 40
- 239000000543 intermediate Substances 0.000 description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 36
- 239000002904 solvent Substances 0.000 description 30
- 150000004677 hydrates Chemical class 0.000 description 29
- 239000012044 organic layer Substances 0.000 description 29
- 229910052801 chlorine Inorganic materials 0.000 description 27
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 23
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 23
- 238000009472 formulation Methods 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000000741 silica gel Substances 0.000 description 21
- 229910002027 silica gel Inorganic materials 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 20
- 239000012267 brine Substances 0.000 description 20
- 238000004440 column chromatography Methods 0.000 description 20
- 229920006395 saturated elastomer Polymers 0.000 description 20
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 20
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 19
- 229940079593 drug Drugs 0.000 description 19
- 230000003595 spectral effect Effects 0.000 description 19
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 18
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 239000000463 material Substances 0.000 description 15
- 239000000377 silicon dioxide Substances 0.000 description 15
- 239000003826 tablet Substances 0.000 description 15
- 241000894006 Bacteria Species 0.000 description 14
- INSWZAQOISIYDT-UHFFFAOYSA-N imidazo[1,2-a]pyrimidine Chemical compound C1=CC=NC2=NC=CN21 INSWZAQOISIYDT-UHFFFAOYSA-N 0.000 description 14
- 239000000546 pharmaceutical excipient Substances 0.000 description 14
- 238000002953 preparative HPLC Methods 0.000 description 14
- 241001465754 Metazoa Species 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 13
- 238000001665 trituration Methods 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 229910052799 carbon Inorganic materials 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
- 229910000027 potassium carbonate Inorganic materials 0.000 description 12
- 235000015320 potassium carbonate Nutrition 0.000 description 12
- 239000003755 preservative agent Substances 0.000 description 12
- 238000000746 purification Methods 0.000 description 12
- 239000000725 suspension Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 235000017557 sodium bicarbonate Nutrition 0.000 description 11
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 10
- 235000014113 dietary fatty acids Nutrition 0.000 description 10
- 239000000194 fatty acid Substances 0.000 description 10
- 229930195729 fatty acid Natural products 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 239000000651 prodrug Substances 0.000 description 10
- 229940002612 prodrug Drugs 0.000 description 10
- 125000006413 ring segment Chemical group 0.000 description 10
- 230000001225 therapeutic effect Effects 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- 101100222170 Bacillus subtilis (strain 168) cssS gene Proteins 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 9
- 210000004027 cell Anatomy 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 8
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- 125000004429 atom Chemical group 0.000 description 8
- 239000000796 flavoring agent Substances 0.000 description 8
- 125000004175 fluorobenzyl group Chemical group 0.000 description 8
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- 239000004094 surface-active agent Substances 0.000 description 8
- PVTXJGJDOHYFOX-UHFFFAOYSA-N 2h-1,4-benzoxazine Chemical compound C1=CC=C2N=CCOC2=C1 PVTXJGJDOHYFOX-UHFFFAOYSA-N 0.000 description 7
- 229920002261 Corn starch Polymers 0.000 description 7
- 239000004150 EU approved colour Substances 0.000 description 7
- 241000282414 Homo sapiens Species 0.000 description 7
- 241000588747 Klebsiella pneumoniae Species 0.000 description 7
- 150000001204 N-oxides Chemical class 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
- 239000004480 active ingredient Substances 0.000 description 7
- 239000007900 aqueous suspension Substances 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 239000002775 capsule Substances 0.000 description 7
- 238000004587 chromatography analysis Methods 0.000 description 7
- 239000003085 diluting agent Substances 0.000 description 7
- 239000000314 lubricant Substances 0.000 description 7
- 229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
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- 239000000375 suspending agent Substances 0.000 description 7
- 239000003765 sweetening agent Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 239000011230 binding agent Substances 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
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- 235000003599 food sweetener Nutrition 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 239000002480 mineral oil Substances 0.000 description 6
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- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 5
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- 108010010803 Gelatin Proteins 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 5
- 235000021355 Stearic acid Nutrition 0.000 description 5
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 5
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- 239000003242 anti bacterial agent Substances 0.000 description 5
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- 239000004599 antimicrobial Substances 0.000 description 5
- 230000003115 biocidal effect Effects 0.000 description 5
- 239000001506 calcium phosphate Substances 0.000 description 5
- 229910000389 calcium phosphate Inorganic materials 0.000 description 5
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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 5
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
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- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 4
- NUAIPKMBWNVQIM-UHFFFAOYSA-N 2-bromo-1-(3,4-dimethoxyphenyl)ethanone Chemical compound COC1=CC=C(C(=O)CBr)C=C1OC NUAIPKMBWNVQIM-UHFFFAOYSA-N 0.000 description 4
- IZHVBANLECCAGF-UHFFFAOYSA-N 2-hydroxy-3-(octadecanoyloxy)propyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCCCC IZHVBANLECCAGF-UHFFFAOYSA-N 0.000 description 4
- NIGBUKPEJHINOG-UHFFFAOYSA-N 4-Acetyl-2-methylpyridine Chemical compound CC(=O)C1=CC=NC(C)=C1 NIGBUKPEJHINOG-UHFFFAOYSA-N 0.000 description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 4
- 239000005695 Ammonium acetate Substances 0.000 description 4
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- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
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- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- 239000008279 sol Substances 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000007892 solid unit dosage form Substances 0.000 description 1
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- 239000004334 sorbic acid Substances 0.000 description 1
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- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
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- 150000003431 steroids Chemical class 0.000 description 1
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- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 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
- 101150054171 thf1 gene Proteins 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
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- 230000000699 topical effect Effects 0.000 description 1
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- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- PRXNKYBFWAWBNZ-UHFFFAOYSA-N trimethylphenylammonium tribromide Chemical compound Br[Br-]Br.C[N+](C)(C)C1=CC=CC=C1 PRXNKYBFWAWBNZ-UHFFFAOYSA-N 0.000 description 1
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- MYPYJXKWCTUITO-LYRMYLQWSA-N vancomycin Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-N 0.000 description 1
- 229960003165 vancomycin Drugs 0.000 description 1
- MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
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- 230000001018 virulence Effects 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- 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
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Warehouses Or Storage Devices (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1718285.8 | 2017-11-03 | ||
| GBGB1718285.8A GB201718285D0 (en) | 2017-11-03 | 2017-11-03 | Antibacterial Compounds |
| PCT/GB2018/053183 WO2019086890A1 (en) | 2017-11-03 | 2018-11-02 | Antibacterial compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA3081423A1 true CA3081423A1 (en) | 2019-05-09 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA3081423A Pending CA3081423A1 (en) | 2017-11-03 | 2018-11-02 | Antibacterial compounds |
Country Status (23)
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| EP (2) | EP3704105B9 (enExample) |
| JP (2) | JP7348897B2 (enExample) |
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| BR (1) | BR112020008531A2 (enExample) |
| CA (1) | CA3081423A1 (enExample) |
| CL (2) | CL2020001147A1 (enExample) |
| CO (1) | CO2020005420A2 (enExample) |
| EA (1) | EA202091118A1 (enExample) |
| ES (1) | ES3005164T3 (enExample) |
| GB (1) | GB201718285D0 (enExample) |
| GE (1) | GEP20237522B (enExample) |
| IL (1) | IL274229B2 (enExample) |
| MA (1) | MA50504A (enExample) |
| MX (2) | MX2020004562A (enExample) |
| NZ (1) | NZ764310A (enExample) |
| PE (2) | PE20211390A1 (enExample) |
| SG (1) | SG11202003717UA (enExample) |
| UA (1) | UA128475C2 (enExample) |
| WO (1) | WO2019086890A1 (enExample) |
| ZA (1) | ZA202002093B (enExample) |
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| GB201718285D0 (en) * | 2017-11-03 | 2017-12-20 | Discuva Ltd | Antibacterial Compounds |
| HUE066783T2 (hu) | 2018-04-18 | 2024-09-28 | Constellation Pharmaceuticals Inc | Metil módosító enzimek modulátorai, ezek készítményei és alkalmazásuk |
| WO2019226491A1 (en) | 2018-05-21 | 2019-11-28 | Constellation Pharmaceuticals, Inc. | Modulators of methyl modifying enzymes, compositions and uses thereof |
| CN111635372B (zh) * | 2020-06-28 | 2022-05-27 | 齐鲁工业大学 | 一种恶唑酮衍生物及其合成方法 |
| EP4333854A1 (en) * | 2021-05-03 | 2024-03-13 | Discuva Ltd. | Antibacterial compound |
| EP4484609A1 (en) | 2022-02-21 | 2025-01-01 | Mitsui Chemicals, Inc. | Metal member, metal-resin composite body, and method for producing metal member |
| CN120208965B (zh) * | 2025-05-28 | 2025-08-12 | 四川大学 | 靶向革兰氏阴性菌外膜组装关键蛋白质机器的4-(吡啶-4-基)-1h-咪唑-2-胺类衍生物、组合物 |
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| ZA869348B (en) | 1985-12-12 | 1987-10-28 | Smithkline Beckman Corp | Inhibition of the 5-lipoxygenase pathway |
| US4780470A (en) * | 1986-08-19 | 1988-10-25 | Smithkline Beckman Corporation | Inhibition of interleukin-1 by monocytes and/or macrophages |
| JP2808460B2 (ja) * | 1989-11-16 | 1998-10-08 | 大正製薬株式会社 | イミダゾール誘導体 |
| JPH09124640A (ja) | 1995-08-25 | 1997-05-13 | Nippon Soda Co Ltd | ピリジルイミダゾール化合物、製法および農園芸用殺菌剤 |
| US6207687B1 (en) | 1998-07-31 | 2001-03-27 | Merck & Co., Inc. | Substituted imidazoles having cytokine inhibitory activity |
| AR029803A1 (es) * | 2000-02-21 | 2003-07-16 | Smithkline Beecham Plc | Imidazoles sustituidos con piridilo y composiciones farmaceuticas que las comprenden |
| EP1532118A2 (en) * | 2002-07-05 | 2005-05-25 | Axxima Pharmaceuticals Aktiengesellschaft | Imidazole compounds for the treatment of hepatitis c virus infections |
| JP2004196678A (ja) | 2002-12-17 | 2004-07-15 | Dainippon Pharmaceut Co Ltd | ピラゾール系誘導体 |
| WO2005047266A1 (en) | 2003-11-14 | 2005-05-26 | Lorus Therapeutics Inc. | Aryl imidazoles and their use as anti-cancer agents |
| WO2005085241A1 (ja) * | 2004-03-05 | 2005-09-15 | Taisho Pharmaceutical Co., Ltd. | チアゾール誘導体 |
| JP2007277230A (ja) * | 2006-03-15 | 2007-10-25 | Tanabe Seiyaku Co Ltd | 医薬組成物 |
| US8865732B2 (en) | 2008-03-21 | 2014-10-21 | Novartis Ag | Heterocyclic compounds and uses thereof |
| EP2513064B1 (en) * | 2009-12-17 | 2018-07-04 | Katholieke Universiteit Leuven K.U. Leuven R&D | Compounds, compositions and methods for controlling biofilms |
| GB201016261D0 (en) | 2010-09-28 | 2010-11-10 | Univ Leuven Kath | Compounds for controlling biofilms and process for their production |
| WO2012135016A2 (en) | 2011-03-25 | 2012-10-04 | North Carolina State University | Inhibition of bacterial biofilms and microbial growth with imidazole derivatives |
| PL2731949T3 (pl) * | 2011-07-13 | 2018-10-31 | Tiumbio Co., Ltd. | 2-pirydylo podstawione imidazole jako inhibitory alk5 i/lub alk4 |
| US8840912B2 (en) | 2012-01-09 | 2014-09-23 | North Carolina State University | Imidazole derivatives useful for controlling microbial growth |
| KR102405136B1 (ko) * | 2014-05-16 | 2022-06-07 | 아트리바 테라퓨틱스 게엠베하 | 인플루엔자 바이러스 및 에스. 아우레우스 공감염에 대한 신규한 항-감염 전략 |
| KR20170122799A (ko) | 2015-03-02 | 2017-11-06 | 리겔 파마슈티칼스, 인크. | TGF-β 억제제 |
| US20180044316A1 (en) | 2015-03-05 | 2018-02-15 | University Of Notre Dame Du Lac | Potentiators of beta-lactam antibiotics |
| CA3030582A1 (en) | 2015-07-22 | 2017-01-26 | The Royal Institution For The Advancement Of Learning/Mcgill University | Compounds and uses thereof in the treatment of cancers and other medical conditions |
| GB201718285D0 (en) * | 2017-11-03 | 2017-12-20 | Discuva Ltd | Antibacterial Compounds |
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2017
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2018
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- 2018-11-02 CN CN201880085171.5A patent/CN111566099B/zh active Active
- 2018-11-02 PE PE2022000118A patent/PE20221006A1/es unknown
- 2018-11-02 CA CA3081423A patent/CA3081423A1/en active Pending
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- 2018-11-02 EA EA202091118A patent/EA202091118A1/ru unknown
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- 2018-11-02 GE GEAP201815801A patent/GEP20237522B/en unknown
- 2018-11-02 EP EP24200101.4A patent/EP4606375A3/en active Pending
- 2018-11-02 UA UAA202003341A patent/UA128475C2/uk unknown
- 2018-11-02 ES ES18800297T patent/ES3005164T3/es active Active
- 2018-11-02 KR KR1020207015574A patent/KR102470319B1/ko active Active
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2021
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2022
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