JP7348897B2 - 抗菌性化合物 - Google Patents
抗菌性化合物 Download PDFInfo
- Publication number
- JP7348897B2 JP7348897B2 JP2020524275A JP2020524275A JP7348897B2 JP 7348897 B2 JP7348897 B2 JP 7348897B2 JP 2020524275 A JP2020524275 A JP 2020524275A JP 2020524275 A JP2020524275 A JP 2020524275A JP 7348897 B2 JP7348897 B2 JP 7348897B2
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- Prior art keywords
- alkyl
- group
- phenyl
- cycloalkyl
- optionally substituted
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 243
- 230000000844 anti-bacterial effect Effects 0.000 title description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 506
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 388
- 125000001424 substituent group Chemical group 0.000 claims description 242
- 229910052739 hydrogen Inorganic materials 0.000 claims description 220
- 239000001257 hydrogen Substances 0.000 claims description 220
- PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims description 194
- 150000002367 halogens Chemical class 0.000 claims description 193
- 229910052736 halogen Inorganic materials 0.000 claims description 192
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 179
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 168
- 150000002431 hydrogen Chemical class 0.000 claims description 155
- -1 quaternary ammonium cations Chemical class 0.000 claims description 155
- 150000003839 salts Chemical class 0.000 claims description 119
- 125000000623 heterocyclic group Chemical group 0.000 claims description 109
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 103
- 125000004076 pyridyl group Chemical group 0.000 claims description 103
- 239000012453 solvate Substances 0.000 claims description 101
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 100
- 125000003545 alkoxy group Chemical group 0.000 claims description 79
- 239000000203 mixture Substances 0.000 claims description 76
- 150000001413 amino acids Chemical class 0.000 claims description 71
- 229910052731 fluorine Inorganic materials 0.000 claims description 66
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 65
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 63
- 229910052801 chlorine Inorganic materials 0.000 claims description 56
- 125000002950 monocyclic group Chemical group 0.000 claims description 52
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 45
- 239000008194 pharmaceutical composition Substances 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 38
- 238000011282 treatment Methods 0.000 claims description 37
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 32
- 241000588921 Enterobacteriaceae Species 0.000 claims description 29
- 201000010099 disease Diseases 0.000 claims description 28
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 26
- 208000015181 infectious disease Diseases 0.000 claims description 26
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 16
- 125000004122 cyclic group Chemical group 0.000 claims description 15
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
- 125000003277 amino group Chemical group 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 8
- 239000003937 drug carrier Substances 0.000 claims description 7
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 5
- 230000002265 prevention Effects 0.000 claims description 2
- 102100034184 Macrophage scavenger receptor types I and II Human genes 0.000 claims 1
- 101710134306 Macrophage scavenger receptor types I and II Proteins 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 description 130
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 113
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 96
- 230000002829 reductive effect Effects 0.000 description 92
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- 238000006243 chemical reaction Methods 0.000 description 79
- 239000000243 solution Substances 0.000 description 76
- 239000007787 solid Substances 0.000 description 72
- 239000011734 sodium Substances 0.000 description 58
- 235000001014 amino acid Nutrition 0.000 description 57
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- 238000005481 NMR spectroscopy Methods 0.000 description 38
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 37
- 239000003795 chemical substances by application Substances 0.000 description 35
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- 150000004677 hydrates Chemical class 0.000 description 30
- 239000012044 organic layer Substances 0.000 description 29
- 125000001072 heteroaryl group Chemical group 0.000 description 25
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- 229920006395 saturated elastomer Polymers 0.000 description 21
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 20
- 238000009472 formulation Methods 0.000 description 20
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- 229910002027 silica gel Inorganic materials 0.000 description 20
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 20
- 238000004440 column chromatography Methods 0.000 description 19
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
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- 239000000546 pharmaceutical excipient Substances 0.000 description 17
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
- 239000002585 base Substances 0.000 description 15
- 241001465754 Metazoa Species 0.000 description 13
- 239000000463 material Substances 0.000 description 13
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000003755 preservative agent Substances 0.000 description 12
- 238000000746 purification Methods 0.000 description 12
- 229910052717 sulfur Inorganic materials 0.000 description 12
- 239000000725 suspension Substances 0.000 description 12
- 125000004093 cyano group Chemical group *C#N 0.000 description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
- 125000004429 atom Chemical group 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
- 239000000377 silicon dioxide Substances 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 208000035143 Bacterial infection Diseases 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 230000000845 anti-microbial effect Effects 0.000 description 9
- 210000004027 cell Anatomy 0.000 description 9
- 230000014759 maintenance of location Effects 0.000 description 9
- 229910052760 oxygen Inorganic materials 0.000 description 9
- 238000002953 preparative HPLC Methods 0.000 description 9
- 230000001225 therapeutic effect Effects 0.000 description 9
- TWHICKSEOJQHOZ-UHFFFAOYSA-N 4-(3,4-dimethoxyphenyl)-5-(2-methylpyridin-4-yl)-1H-imidazol-2-amine Chemical compound COC=1C=C(C=CC=1OC)C1=C(N=C(N1)N)C1=CC(=NC=C1)C TWHICKSEOJQHOZ-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
- 125000002947 alkylene group Chemical group 0.000 description 8
- 239000003242 anti bacterial agent Substances 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- 239000003086 colorant Substances 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 229920002261 Corn starch Polymers 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 150000001204 N-oxides Chemical class 0.000 description 7
- 229960000583 acetic acid Drugs 0.000 description 7
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- 208000022362 bacterial infectious disease Diseases 0.000 description 7
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- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
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- 229940088710 antibiotic agent Drugs 0.000 description 6
- 239000011230 binding agent Substances 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
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- C—CHEMISTRY; METALLURGY
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- 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
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- 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
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- 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
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- C—CHEMISTRY; METALLURGY
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| 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 |
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| 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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| 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 |
| 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 |
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| 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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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2011080132A2 (en) | 2009-12-17 | 2011-07-07 | Katholieke Universiteit Leuven, K.U. Leuven R&D | Compounds, compositions and methods for controlling biofilms |
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