DK2373631T3 - antibacterials - Google Patents

Info

Publication number

DK2373631T3

DK2373631T3 DK09795514.0T DK09795514T DK2373631T3 DK 2373631 T3 DK2373631 T3 DK 2373631T3 DK 09795514 T DK09795514 T DK 09795514T DK 2373631 T3 DK2373631 T3 DK 2373631T3

Authority

DK

Denmark

Prior art keywords

compound

bibenzo

imidazole

use according

compounds

Prior art date

2008-12-02

Links

• Espacenet
• Global Dossier
• Discuss

• 229940088710 antibiotic agent Drugs 0.000 title description 15
• 230000000844 anti-bacterial effect Effects 0.000 title description 7
• 150000001875 compounds Chemical class 0.000 claims description 142
• 229910052739 hydrogen Inorganic materials 0.000 claims description 67
• 241000193163 Clostridioides difficile Species 0.000 claims description 54
• 238000000034 method Methods 0.000 claims description 44
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 39
• 201000010099 disease Diseases 0.000 claims description 36
• -1 1'H-5,5'-bibenzo [d] imidazole-2,2'-diyl Chemical group 0.000 claims description 29
• 238000011282 treatment Methods 0.000 claims description 23
• 150000003839 salts Chemical class 0.000 claims description 19
• 125000003118 aryl group Chemical group 0.000 claims description 16
• 125000005843 halogen group Chemical group 0.000 claims description 16
• 208000015181 infectious disease Diseases 0.000 claims description 14
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
• 206010012735 Diarrhoea Diseases 0.000 claims description 11
• 206010009887 colitis Diseases 0.000 claims description 11
• 239000012453 solvate Substances 0.000 claims description 10
• 125000000217 alkyl group Chemical group 0.000 claims description 9
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 8
• 108010059993 Vancomycin Proteins 0.000 claims description 8
• 125000001072 heteroaryl group Chemical group 0.000 claims description 8
• 125000001424 substituent group Chemical group 0.000 claims description 8
• 229960003165 vancomycin Drugs 0.000 claims description 8
• 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 claims description 8
• 229960000282 metronidazole Drugs 0.000 claims description 7
• VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 claims description 7
• 206010009657 Clostridium difficile colitis Diseases 0.000 claims description 6
• 229940077716 histamine h2 receptor antagonists for peptic ulcer and gord Drugs 0.000 claims description 6
• QGMGHALXLXKCBD-UHFFFAOYSA-N 4-amino-n-(2-aminophenyl)benzamide Chemical compound C1=CC(N)=CC=C1C(=O)NC1=CC=CC=C1N QGMGHALXLXKCBD-UHFFFAOYSA-N 0.000 claims description 5
• 208000003100 Pseudomembranous Enterocolitis Diseases 0.000 claims description 5
• 206010037128 Pseudomembranous colitis Diseases 0.000 claims description 5
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 5
• 235000013305 food Nutrition 0.000 claims description 5
• 150000001204 N-oxides Chemical class 0.000 claims description 4
• 229910052799 carbon Inorganic materials 0.000 claims description 4
• 125000004122 cyclic group Chemical group 0.000 claims description 4
• 125000000623 heterocyclic group Chemical group 0.000 claims description 4
• 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 4
• 150000004677 hydrates Chemical class 0.000 claims description 3
• 229910052760 oxygen Inorganic materials 0.000 claims description 3
• 229940126409 proton pump inhibitor Drugs 0.000 claims description 3
• 239000000612 proton pump inhibitor Substances 0.000 claims description 3
• XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 claims description 2
• MTXGSGLDYXIXFF-UHFFFAOYSA-N 4-[6-[2-(4-aminophenyl)-3h-benzimidazol-5-yl]-1h-benzimidazol-2-yl]aniline Chemical compound C1=CC(N)=CC=C1C1=NC2=CC=C(C=3C=C4NC(=NC4=CC=3)C=3C=CC(N)=CC=3)C=C2N1 MTXGSGLDYXIXFF-UHFFFAOYSA-N 0.000 claims description 2
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
• 230000000968 intestinal effect Effects 0.000 claims description 2
• 238000005399 mechanical ventilation Methods 0.000 claims description 2
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
• 229910052717 sulfur Inorganic materials 0.000 claims description 2
• 101100134925 Gallus gallus COR6 gene Proteins 0.000 claims 3
• UHQFBTAJFNVZIV-UHFFFAOYSA-N 2-pyridin-4-yl-6-(2-pyridin-4-yl-3h-benzimidazol-5-yl)-1h-benzimidazole Chemical compound C1=NC=CC(C=2NC3=CC=C(C=C3N=2)C=2C=C3N=C(NC3=CC=2)C=2C=CN=CC=2)=C1 UHQFBTAJFNVZIV-UHFFFAOYSA-N 0.000 claims 2
• AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 claims 2
• 125000004076 pyridyl group Chemical group 0.000 claims 2
• 238000006467 substitution reaction Methods 0.000 claims 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
• IQEWIIWKWPCQIU-UHFFFAOYSA-N 2-(4-methoxyphenyl)-6-(2-phenyl-3h-benzimidazol-5-yl)-1h-benzimidazole Chemical compound C1=CC(OC)=CC=C1C1=NC2=CC=C(C=3C=C4N=C(NC4=CC=3)C=3C=CC=CC=3)C=C2N1 IQEWIIWKWPCQIU-UHFFFAOYSA-N 0.000 claims 1
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
• UHUVPVREKSWRCU-UHFFFAOYSA-N 5-[6-[2-(6-aminopyridin-3-yl)-3h-benzimidazol-5-yl]-1h-benzimidazol-2-yl]pyridin-2-amine Chemical compound C1=NC(N)=CC=C1C1=NC2=CC(C=3C=C4N=C(NC4=CC=3)C=3C=NC(N)=CC=3)=CC=C2N1 UHUVPVREKSWRCU-UHFFFAOYSA-N 0.000 claims 1
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
• 238000011863 diuretic therapy Methods 0.000 claims 1
• 239000001257 hydrogen Substances 0.000 claims 1
• 239000006041 probiotic Substances 0.000 claims 1
• 230000000529 probiotic effect Effects 0.000 claims 1
• 235000018291 probiotics Nutrition 0.000 claims 1
• 125000003107 substituted aryl group Chemical group 0.000 claims 1
• MYPYJXKWCTUITO-LYRMYLQWSA-O vancomycin(1+) 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)[NH2+]C)[C@H]1C[C@](C)([NH3+])[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-O 0.000 claims 1
• 239000000203 mixture Substances 0.000 description 59
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 43
• 239000003795 chemical substances by application Substances 0.000 description 42
• 230000000694 effects Effects 0.000 description 31
• 241000894006 Bacteria Species 0.000 description 27
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
• 238000005160 1H NMR spectroscopy Methods 0.000 description 22
• 239000007787 solid Substances 0.000 description 19
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
• 239000000243 solution Substances 0.000 description 17
• 239000003242 anti bacterial agent Substances 0.000 description 16
• 210000004215 spore Anatomy 0.000 description 15
• 239000003826 tablet Substances 0.000 description 15
• 230000003385 bacteriostatic effect Effects 0.000 description 14
• 125000004432 carbon atom Chemical group C* 0.000 description 14
• 238000009472 formulation Methods 0.000 description 14
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
• 239000003814 drug Substances 0.000 description 13
• 150000002430 hydrocarbons Chemical group 0.000 description 13
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 13
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
• 230000003115 biocidal effect Effects 0.000 description 12
• 239000000546 pharmaceutical excipient Substances 0.000 description 12
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• 239000000047 product Substances 0.000 description 12
• 241000193738 Bacillus anthracis Species 0.000 description 11
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• 235000019439 ethyl acetate Nutrition 0.000 description 11
• 210000001035 gastrointestinal tract Anatomy 0.000 description 11
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
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• 241000193403 Clostridium Species 0.000 description 9
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• 239000002244 precipitate Substances 0.000 description 9
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• 239000004150 EU approved colour Substances 0.000 description 7
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
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• 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 7
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