KR20150088292A - 광범위한 마크로사이클릭 항생제 - Google Patents

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Publication number

KR20150088292A

KR20150088292A KR1020157016534A KR20157016534A KR20150088292A KR 20150088292 A KR20150088292 A KR 20150088292A KR 1020157016534 A KR1020157016534 A KR 1020157016534A KR 20157016534 A KR20157016534 A KR 20157016534A KR 20150088292 A KR20150088292 A KR 20150088292A

Authority

KR

South Korea

Prior art keywords

alkyl

optionally substituted

formula

rti

independently

Prior art date

2012-11-21

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.)

Withdrawn

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• 239000003242 anti bacterial agent Substances 0.000 title description 6
• 229940088710 antibiotic agent Drugs 0.000 title description 5
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• 238000000034 method Methods 0.000 claims abstract description 58
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• 206010057190 Respiratory tract infections Diseases 0.000 claims description 648
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 290
• 125000000217 alkyl group Chemical group 0.000 claims description 262
• 125000001072 heteroaryl group Chemical group 0.000 claims description 235
• -1 cyano, hydroxy Chemical group 0.000 claims description 220
• 125000004432 carbon atom Chemical group C* 0.000 claims description 183
• 229910052739 hydrogen Inorganic materials 0.000 claims description 182
• 125000003118 aryl group Chemical group 0.000 claims description 181
• 125000000623 heterocyclic group Chemical group 0.000 claims description 166
• VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical group [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 claims description 138
• 239000001257 hydrogen Substances 0.000 claims description 135
• 229910052799 carbon Inorganic materials 0.000 claims description 125
• ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 110
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 109
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 82
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 79
• 229910052796 boron Inorganic materials 0.000 claims description 74
• 150000002431 hydrogen Chemical class 0.000 claims description 74
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 72
• 150000003839 salts Chemical class 0.000 claims description 67
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 66
• 239000004202 carbamide Substances 0.000 claims description 65
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 60
• 125000000304 alkynyl group Chemical group 0.000 claims description 60
• 125000003342 alkenyl group Chemical group 0.000 claims description 58
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 53
• 125000002947 alkylene group Chemical group 0.000 claims description 46
• 125000003107 substituted aryl group Chemical group 0.000 claims description 46
• 229910052760 oxygen Inorganic materials 0.000 claims description 45
• 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 claims description 45
• 229910052717 sulfur Inorganic materials 0.000 claims description 43
• 229940002612 prodrug Drugs 0.000 claims description 42
• 239000000651 prodrug Substances 0.000 claims description 42
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 36
• 239000012453 solvate Substances 0.000 claims description 36
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• 208000022362 bacterial infectious disease Diseases 0.000 claims description 29
• 150000001721 carbon Chemical group 0.000 claims description 28
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 28
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 27
• 229910052794 bromium Inorganic materials 0.000 claims description 26
• 229910052801 chlorine Inorganic materials 0.000 claims description 26
• 241000191967 Staphylococcus aureus Species 0.000 claims description 25
• 229910052731 fluorine Inorganic materials 0.000 claims description 22
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
• 241000124008 Mammalia Species 0.000 claims description 21
• 229910052740 iodine Inorganic materials 0.000 claims description 21
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 20
• 229910052736 halogen Inorganic materials 0.000 claims description 20
• 150000002367 halogens Chemical group 0.000 claims description 20
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 20
• 125000005309 thioalkoxy group Chemical group 0.000 claims description 19
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 19
• 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims description 18
• 125000006717 (C3-C10) cycloalkenyl group Chemical group 0.000 claims description 18
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 18
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 18
• 208000015181 infectious disease Diseases 0.000 claims description 18
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 18
• 125000004423 acyloxy group Chemical group 0.000 claims description 17
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 16
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 16
• 230000004962 physiological condition Effects 0.000 claims description 16
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 15
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• 229940124587 cephalosporin Drugs 0.000 claims description 13
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• 241000193998 Streptococcus pneumoniae Species 0.000 claims description 9
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 9
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• 230000009286 beneficial effect Effects 0.000 claims description 6
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• 241000588724 Escherichia coli Species 0.000 claims description 5
• 241000590002 Helicobacter pylori Species 0.000 claims description 5
• 241000588747 Klebsiella pneumoniae Species 0.000 claims description 5
• 241000186779 Listeria monocytogenes Species 0.000 claims description 5
• 229930182555 Penicillin Natural products 0.000 claims description 5
• JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 claims description 5
• 241000588770 Proteus mirabilis Species 0.000 claims description 5
• 241000588767 Proteus vulgaris Species 0.000 claims description 5
• 241000589517 Pseudomonas aeruginosa Species 0.000 claims description 5
• 241000589540 Pseudomonas fluorescens Species 0.000 claims description 5
• 241000589776 Pseudomonas putida Species 0.000 claims description 5
• 241001354013 Salmonella enterica subsp. enterica serovar Enteritidis Species 0.000 claims description 5
• 241000531795 Salmonella enterica subsp. enterica serovar Paratyphi A Species 0.000 claims description 5
• 241000607762 Shigella flexneri Species 0.000 claims description 5
• 241000191980 Staphylococcus intermedius Species 0.000 claims description 5
• 241000122973 Stenotrophomonas maltophilia Species 0.000 claims description 5
• 241000607626 Vibrio cholerae Species 0.000 claims description 5
• 241000607734 Yersinia <bacteria> Species 0.000 claims description 5
• 229940037467 helicobacter pylori Drugs 0.000 claims description 5
• 229940049954 penicillin Drugs 0.000 claims description 5
• 229940007042 proteus vulgaris Drugs 0.000 claims description 5
• 241000589969 Borreliella burgdorferi Species 0.000 claims description 4
• 241000589876 Campylobacter Species 0.000 claims description 4
• 241000589877 Campylobacter coli Species 0.000 claims description 4
• 241000589874 Campylobacter fetus Species 0.000 claims description 4
• 241000589875 Campylobacter jejuni Species 0.000 claims description 4
• 241000193163 Clostridioides difficile Species 0.000 claims description 4
• 241000606822 Haemophilus parahaemolyticus Species 0.000 claims description 4
• 241000588749 Klebsiella oxytoca Species 0.000 claims description 4
• 241000186364 Mycobacterium intracellulare Species 0.000 claims description 4
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• 241000187479 Mycobacterium tuberculosis Species 0.000 claims description 4
• 241000588768 Providencia Species 0.000 claims description 4
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• 241000607447 Yersinia enterocolitica Species 0.000 claims description 4
• 241000607481 Yersinia intermedia Species 0.000 claims description 4
• 229940126574 aminoglycoside antibiotic Drugs 0.000 claims description 4
• 239000002647 aminoglycoside antibiotic agent Substances 0.000 claims description 4
• WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 claims description 4
• 229960005091 chloramphenicol Drugs 0.000 claims description 4
• 239000003910 polypeptide antibiotic agent Substances 0.000 claims description 4
• 239000003306 quinoline derived antiinfective agent Substances 0.000 claims description 4
• 229960001225 rifampicin Drugs 0.000 claims description 4
• 229940030998 streptococcus agalactiae Drugs 0.000 claims description 4
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• 229940126085 β‑Lactamase Inhibitor Drugs 0.000 claims description 3
• SHXWCVYOXRDMCX-UHFFFAOYSA-N 3,4-methylenedioxymethamphetamine Chemical compound CNC(C)CC1=CC=C2OCOC2=C1 SHXWCVYOXRDMCX-UHFFFAOYSA-N 0.000 claims description 2
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