KR20140097118A - 항균 화합물 및 이의 사용 방법 - Google Patents

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Publication number

KR20140097118A

KR20140097118A KR1020147008210A KR20147008210A KR20140097118A KR 20140097118 A KR20140097118 A KR 20140097118A KR 1020147008210 A KR1020147008210 A KR 1020147008210A KR 20147008210 A KR20147008210 A KR 20147008210A KR 20140097118 A KR20140097118 A KR 20140097118A

Authority

KR

South Korea

Prior art keywords

alkyl

oxo

carboxylic acid

methyl

dihydropyridine

Prior art date

2011-08-29

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Withdrawn

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 374
• 238000000034 method Methods 0.000 title claims description 241
• 230000000844 anti-bacterial effect Effects 0.000 title description 6
• 208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 58
• 208000035143 Bacterial infection Diseases 0.000 claims abstract description 53
• 239000003814 drug Substances 0.000 claims abstract description 26
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 22
• 229940079593 drug Drugs 0.000 claims abstract description 13
• 125000000217 alkyl group Chemical group 0.000 claims description 955
• -1 carboxy, amino Chemical group 0.000 claims description 834
• 239000002253 acid Substances 0.000 claims description 277
• 125000003118 aryl group Chemical group 0.000 claims description 242
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 202
• 125000003282 alkyl amino group Chemical group 0.000 claims description 151
• GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 147
• 125000000623 heterocyclic group Chemical group 0.000 claims description 122
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 105
• 125000001072 heteroaryl group Chemical group 0.000 claims description 104
• 206010057190 Respiratory tract infections Diseases 0.000 claims description 95
• 125000003545 alkoxy group Chemical group 0.000 claims description 90
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 79
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 75
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 64
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 64
• 125000005843 halogen group Chemical group 0.000 claims description 59
• 150000003839 salts Chemical class 0.000 claims description 58
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 57
• 125000001424 substituent group Chemical group 0.000 claims description 48
• 241000894006 Bacteria Species 0.000 claims description 31
• 125000001769 aryl amino group Chemical group 0.000 claims description 26
• 239000012453 solvate Substances 0.000 claims description 25
• 125000003342 alkenyl group Chemical group 0.000 claims description 23
• 150000002367 halogens Chemical class 0.000 claims description 23
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 22
• 239000003242 anti bacterial agent Substances 0.000 claims description 21
• 229910052736 halogen Inorganic materials 0.000 claims description 21
• 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 21
• PVNIIMVLHYAWGP-UHFFFAOYSA-N nicotinic acid Natural products OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 19
• 125000000304 alkynyl group Chemical group 0.000 claims description 17
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
• 235000001968 nicotinic acid Nutrition 0.000 claims description 16
• 239000011664 nicotinic acid Substances 0.000 claims description 16
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 15
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 15
• 229910052739 hydrogen Inorganic materials 0.000 claims description 15
• 239000001257 hydrogen Substances 0.000 claims description 15
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 15
• 239000004599 antimicrobial Substances 0.000 claims description 14
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 14
• 125000004076 pyridyl group Chemical group 0.000 claims description 14
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 13
• 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims description 13
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 12
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 12
• MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 claims description 12
• 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 12
• 125000003386 piperidinyl group Chemical group 0.000 claims description 12
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 12
• 241000588724 Escherichia coli Species 0.000 claims description 11
• 125000002393 azetidinyl group Chemical group 0.000 claims description 11
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 11
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 11
• 125000002757 morpholinyl group Chemical group 0.000 claims description 11
• 125000004193 piperazinyl group Chemical group 0.000 claims description 11
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 11
• 125000004605 1,2,3,4-tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 10
• PDXLGSQQIYTOCE-UHFFFAOYSA-N 1,2-dihydropyridine-2-carboxylic acid;hydrochloride Chemical compound Cl.OC(=O)C1NC=CC=C1 PDXLGSQQIYTOCE-UHFFFAOYSA-N 0.000 claims description 10
• 125000002619 bicyclic group Chemical group 0.000 claims description 10
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 10
• UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 10
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 10
• 125000005960 1,4-diazepanyl group Chemical group 0.000 claims description 9
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 9
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
• 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 9
• 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 8
• 241000194032 Enterococcus faecalis Species 0.000 claims description 8
• 125000006319 alkynyl amino group Chemical group 0.000 claims description 8
• 229940032049 enterococcus faecalis Drugs 0.000 claims description 8
• 125000001041 indolyl group Chemical group 0.000 claims description 8
• 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 8
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 8
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 7
• 125000004414 alkyl thio group Chemical group 0.000 claims description 7
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 7
• 230000003115 biocidal effect Effects 0.000 claims description 7
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
• 125000004043 oxo group Chemical group O=* 0.000 claims description 7
• 241000588626 Acinetobacter baumannii Species 0.000 claims description 6
• 241000191967 Staphylococcus aureus Species 0.000 claims description 6
• 229960003405 ciprofloxacin Drugs 0.000 claims description 6
• 239000012458 free base Substances 0.000 claims description 6
• 125000002883 imidazolyl group Chemical group 0.000 claims description 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 6
• OWOIOZSALARIEF-UHFFFAOYSA-N pyrrolo[2,3-c]pyrrole Chemical compound N1=CC2=CC=NC2=C1 OWOIOZSALARIEF-UHFFFAOYSA-N 0.000 claims description 6
• SSJXIUAHEKJCMH-WDSKDSINSA-N (1s,2s)-cyclohexane-1,2-diamine Chemical compound N[C@H]1CCCC[C@@H]1N SSJXIUAHEKJCMH-WDSKDSINSA-N 0.000 claims description 5
• KTCNGKASVZVXHT-UHFFFAOYSA-N 1,2-dihydropyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CNC1 KTCNGKASVZVXHT-UHFFFAOYSA-N 0.000 claims description 5
• 241000192125 Firmicutes Species 0.000 claims description 5
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
• 241000193998 Streptococcus pneumoniae Species 0.000 claims description 5
• 241000607734 Yersinia <bacteria> Species 0.000 claims description 5
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 5
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 5
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 5
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
• 125000005241 heteroarylamino group Chemical group 0.000 claims description 5
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
• 229940031000 streptococcus pneumoniae Drugs 0.000 claims description 5
• 125000001607 1,2,3-triazol-1-yl group Chemical group [*]N1N=NC([H])=C1[H] 0.000 claims description 4
• JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 claims description 4
• 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims description 4
• 241001156739 Actinobacteria <phylum> Species 0.000 claims description 4
• 241000193738 Bacillus anthracis Species 0.000 claims description 4
• 241000588914 Enterobacter Species 0.000 claims description 4
• 241000588747 Klebsiella pneumoniae Species 0.000 claims description 4
• 241000192142 Proteobacteria Species 0.000 claims description 4
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
• 241000607768 Shigella Species 0.000 claims description 4
• 229940065181 bacillus anthracis Drugs 0.000 claims description 4
• 125000004122 cyclic group Chemical group 0.000 claims description 4
• 229960003702 moxifloxacin Drugs 0.000 claims description 4
• FABPRXSRWADJSP-MEDUHNTESA-N moxifloxacin Chemical compound COC1=C(N2C[C@H]3NCCC[C@H]3C2)C(F)=CC(C(C(C(O)=O)=C2)=O)=C1N2C1CC1 FABPRXSRWADJSP-MEDUHNTESA-N 0.000 claims description 4
• 125000001624 naphthyl group Chemical group 0.000 claims description 4
• UZGLIIJVICEWHF-UHFFFAOYSA-N octogen Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)CN([N+]([O-])=O)C1 UZGLIIJVICEWHF-UHFFFAOYSA-N 0.000 claims description 4
• SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims description 4
• KUKYNIDZZOJQOL-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid;hydrochloride Chemical compound Cl.OC(=O)N1CCCC1 KUKYNIDZZOJQOL-UHFFFAOYSA-N 0.000 claims description 4
• 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims description 4
• 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 4
• 125000000335 thiazolyl group Chemical group 0.000 claims description 4
• 125000001544 thienyl group Chemical group 0.000 claims description 4
• 125000004607 1,2,3,4-tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 3
• 244000063299 Bacillus subtilis Species 0.000 claims description 3
• 235000014469 Bacillus subtilis Nutrition 0.000 claims description 3
• 241000606768 Haemophilus influenzae Species 0.000 claims description 3
• GSDSWSVVBLHKDQ-JTQLQIEISA-N Levofloxacin Chemical compound C([C@@H](N1C2=C(C(C(C(O)=O)=C1)=O)C=C1F)C)OC2=C1N1CCN(C)CC1 GSDSWSVVBLHKDQ-JTQLQIEISA-N 0.000 claims description 3
• 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 3
• 241000589517 Pseudomonas aeruginosa Species 0.000 claims description 3
• 125000006323 alkenyl amino group Chemical group 0.000 claims description 3
• 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 3
• 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 3
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
• 238000002648 combination therapy Methods 0.000 claims description 3
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 3
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• 238000007429 general method Methods 0.000 claims description 3
• 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 3
• 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 claims description 3
• 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 3
• 229960003376 levofloxacin Drugs 0.000 claims description 3
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 3
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• 125000006625 (C3-C8) cycloalkyloxy group Chemical group 0.000 claims description 2
• 125000005955 1H-indazolyl group Chemical group 0.000 claims description 2
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• RJQXTJLFIWVMTO-TYNCELHUSA-N Methicillin Chemical compound COC1=CC=CC(OC)=C1C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@@H]21 RJQXTJLFIWVMTO-TYNCELHUSA-N 0.000 claims description 2
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• 241001180364 Spirochaetes Species 0.000 claims description 2
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• 241000193996 Streptococcus pyogenes Species 0.000 claims description 2
• 241000390529 Synergistetes Species 0.000 claims description 2
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• 125000005605 benzo group Chemical group 0.000 claims description 2
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
• WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims description 2
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• TYZROVQLWOKYKF-ZDUSSCGKSA-N linezolid Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCOCC1 TYZROVQLWOKYKF-ZDUSSCGKSA-N 0.000 claims description 2
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• MHWLWQUZZRMNGJ-UHFFFAOYSA-N nalidixic acid Chemical compound C1=C(C)N=C2N(CC)C=C(C(O)=O)C(=O)C2=C1 MHWLWQUZZRMNGJ-UHFFFAOYSA-N 0.000 claims description 2
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• 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims 6
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• RXZBMPWDPOLZGW-XMRMVWPWSA-N (E)-roxithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=N/OCOCCOC)/[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 RXZBMPWDPOLZGW-XMRMVWPWSA-N 0.000 claims 2
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• AEUTYOVWOVBAKS-UWVGGRQHSA-N ethambutol Chemical compound CC[C@@H](CO)NCCN[C@@H](CC)CO AEUTYOVWOVBAKS-UWVGGRQHSA-N 0.000 claims 2
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