CN111566099B - 抗菌化合物 - Google Patents
抗菌化合物 Download PDFInfo
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- CN111566099B CN111566099B CN201880085171.5A CN201880085171A CN111566099B CN 111566099 B CN111566099 B CN 111566099B CN 201880085171 A CN201880085171 A CN 201880085171A CN 111566099 B CN111566099 B CN 111566099B
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- China
- Prior art keywords
- alkyl
- group
- hydrogen
- cycloalkyl
- optionally substituted
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 243
- 230000000844 anti-bacterial effect Effects 0.000 title description 15
- 238000000034 method Methods 0.000 claims abstract description 99
- 238000011282 treatment Methods 0.000 claims abstract description 90
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 38
- 201000010099 disease Diseases 0.000 claims abstract description 34
- 208000035143 Bacterial infection Diseases 0.000 claims abstract description 26
- 208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 23
- 208000034801 Enterobacteriaceae Infections Diseases 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 345
- 125000001424 substituent group Chemical group 0.000 claims description 177
- 229910052739 hydrogen Inorganic materials 0.000 claims description 173
- 239000001257 hydrogen Substances 0.000 claims description 173
- 229910052736 halogen Inorganic materials 0.000 claims description 130
- 150000002367 halogens Chemical class 0.000 claims description 130
- 150000002431 hydrogen Chemical class 0.000 claims description 120
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 111
- 125000004076 pyridyl group Chemical group 0.000 claims description 87
- 150000003839 salts Chemical class 0.000 claims description 87
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 77
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 75
- 125000003545 alkoxy group Chemical group 0.000 claims description 66
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 53
- 229910052731 fluorine Inorganic materials 0.000 claims description 49
- 125000002950 monocyclic group Chemical group 0.000 claims description 42
- 239000003814 drug Substances 0.000 claims description 38
- 239000008194 pharmaceutical composition Substances 0.000 claims description 31
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 125000005189 alkyl hydroxy group Chemical group 0.000 claims description 24
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 24
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 21
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 19
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 12
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- 238000002360 preparation method Methods 0.000 claims description 8
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 claims description 5
- 125000006164 6-membered heteroaryl group Chemical group 0.000 claims 1
- 101100379081 Emericella variicolor andC gene Proteins 0.000 claims 1
- 230000000968 intestinal effect Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 83
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 249
- -1 R 15 Amino acid Chemical class 0.000 description 176
- 239000011541 reaction mixture Substances 0.000 description 129
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 108
- 230000002829 reductive effect Effects 0.000 description 91
- 239000000243 solution Substances 0.000 description 80
- 238000006243 chemical reaction Methods 0.000 description 79
- 125000000623 heterocyclic group Chemical group 0.000 description 72
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- 239000007787 solid Substances 0.000 description 69
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 62
- 239000011734 sodium Substances 0.000 description 58
- 150000002148 esters Chemical class 0.000 description 57
- 239000012453 solvate Substances 0.000 description 54
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 47
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- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
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- 125000001453 quaternary ammonium group Chemical group 0.000 description 34
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- 239000002904 solvent Substances 0.000 description 31
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- 150000004677 hydrates Chemical class 0.000 description 29
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- 229920006395 saturated elastomer Polymers 0.000 description 22
- 229910052757 nitrogen Inorganic materials 0.000 description 21
- 239000012267 brine Substances 0.000 description 20
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- 150000003254 radicals Chemical class 0.000 description 20
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 20
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- 125000000753 cycloalkyl group Chemical group 0.000 description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 description 18
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000003826 tablet Substances 0.000 description 15
- 241001465754 Metazoa Species 0.000 description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 13
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical group OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 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
- 229910052799 carbon Inorganic materials 0.000 description 11
- 125000004122 cyclic group Chemical group 0.000 description 11
- 235000014113 dietary fatty acids Nutrition 0.000 description 11
- 239000000194 fatty acid Substances 0.000 description 11
- 229930195729 fatty acid Natural products 0.000 description 11
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 230000014759 maintenance of location Effects 0.000 description 10
- 125000004433 nitrogen atom Chemical group N* 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
- 229910052717 sulfur Inorganic materials 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 125000002947 alkylene group Chemical group 0.000 description 9
- 125000003277 amino group Chemical group 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 238000002953 preparative HPLC Methods 0.000 description 9
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 8
- 125000004429 atom Chemical group 0.000 description 8
- 230000001580 bacterial effect Effects 0.000 description 8
- 210000004027 cell Anatomy 0.000 description 8
- 125000004093 cyano group Chemical group *C#N 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
- 229910052760 oxygen Inorganic materials 0.000 description 8
- 231100000331 toxic Toxicity 0.000 description 8
- 230000002588 toxic effect Effects 0.000 description 8
- 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 7
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- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 7
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- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 6
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- 229940081974 saccharin Drugs 0.000 description 1
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- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
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- 230000002459 sustained effect Effects 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- LFKDJXLFVYVEFG-UHFFFAOYSA-N tert-butyl carbamate Chemical compound CC(C)(C)OC(N)=O LFKDJXLFVYVEFG-UHFFFAOYSA-N 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
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 1
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- 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
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- 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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- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
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- 229940116362 tragacanth Drugs 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 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
- OOLLAFOLCSJHRE-ZHAKMVSLSA-N ulipristal acetate Chemical compound C1=CC(N(C)C)=CC=C1[C@@H]1C2=C3CCC(=O)C=C3CC[C@H]2[C@H](CC[C@]2(OC(C)=O)C(C)=O)[C@]2(C)C1 OOLLAFOLCSJHRE-ZHAKMVSLSA-N 0.000 description 1
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- 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
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Classifications
-
- 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
-
- 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
-
- 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 (2)
| Publication Number | Publication Date |
|---|---|
| CN111566099A CN111566099A (zh) | 2020-08-21 |
| CN111566099B true CN111566099B (zh) | 2023-06-02 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201880085171.5A Active CN111566099B (zh) | 2017-11-03 | 2018-11-02 | 抗菌化合物 |
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|---|---|
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| EP (2) | EP3704105B9 (enExample) |
| JP (2) | JP7348897B2 (enExample) |
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| CA (1) | CA3081423A1 (enExample) |
| CL (2) | CL2020001147A1 (enExample) |
| CO (1) | CO2020005420A2 (enExample) |
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| ES (1) | ES3005164T3 (enExample) |
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| 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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| WO2015173788A1 (en) * | 2014-05-16 | 2015-11-19 | Westfaelische Wilhelms-Universitaet Muenster | Novel anti-infective strategy against influenza virus and s. aureus coinfections |
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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 |
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| 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 |
| 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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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015173788A1 (en) * | 2014-05-16 | 2015-11-19 | Westfaelische Wilhelms-Universitaet Muenster | Novel anti-infective strategy against influenza virus and s. aureus coinfections |
| CN107073123A (zh) * | 2014-05-16 | 2017-08-18 | 归属疗法有限公司 | 抗流感病毒和金黄色葡萄球菌合并感染的新型抗感染策略 |
Non-Patent Citations (2)
| Title |
|---|
| STN检索库中新颖性化合物;REGISTRY;《STN》;20090405;1-6页 * |
| Structure-activity relationship of 4(5)-aryl-2-amino-1H-imidazoles, N1-substituted 2-aminoimidazoles and imidazo[1,2-a]pyrimidinium salts as inhibitors of biofilm formation by Salmonella Typhimurium and Pseudomonas aeruginosa;Hans P. L.Steenackers;《Journal of Medicinal Chemistry》;20101120;第54卷(第2期);第475页table3，化合物11-17 * |
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