JP2020510044A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2020510044A5 JP2020510044A5 JP2019549454A JP2019549454A JP2020510044A5 JP 2020510044 A5 JP2020510044 A5 JP 2020510044A5 JP 2019549454 A JP2019549454 A JP 2019549454A JP 2019549454 A JP2019549454 A JP 2019549454A JP 2020510044 A5 JP2020510044 A5 JP 2020510044A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- carbocyclyl
- compound
- alkoxy
- hydrogen
- Prior art date
- 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.)
- Granted
Links
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 121
- 150000001875 compounds Chemical class 0.000 claims description 84
- 150000003839 salts Chemical class 0.000 claims description 83
- 229910052739 hydrogen Inorganic materials 0.000 claims description 66
- 239000001257 hydrogen Substances 0.000 claims description 65
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 62
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 38
- 150000002431 hydrogen Chemical class 0.000 claims description 37
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 34
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 32
- 125000002950 monocyclic group Chemical group 0.000 claims description 29
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
- 125000001072 heteroaryl group Chemical group 0.000 claims description 26
- -1 methylenedioxy Chemical group 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
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- 208000035143 Bacterial infection Diseases 0.000 claims description 14
- 241001465754 Metazoa Species 0.000 claims description 14
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 14
- 230000001580 bacterial effect Effects 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 8
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
- 239000003242 anti bacterial agent Substances 0.000 claims description 7
- 125000006193 alkinyl group Chemical group 0.000 claims description 6
- 230000002401 inhibitory effect Effects 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 230000000069 prophylactic effect Effects 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 230000001225 therapeutic effect Effects 0.000 claims description 4
- 125000006373 (C2-C10) alkyl group Chemical group 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 230000005764 inhibitory process Effects 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 20
- 239000000203 mixture Substances 0.000 claims 8
- 239000004599 antimicrobial Substances 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 description 28
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 3
- 241000606749 Aggregatibacter actinomycetemcomitans Species 0.000 description 2
- 241000589602 Francisella tularensis Species 0.000 description 2
- 241000588655 Moraxella catarrhalis Species 0.000 description 2
- DIOCHDIROFPRHY-UHFFFAOYSA-N NC(CC1)CCC1NCCNC(c([nH]c1c2)cc1ccc2-c(cc1)ccc1F)=O Chemical compound NC(CC1)CCC1NCCNC(c([nH]c1c2)cc1ccc2-c(cc1)ccc1F)=O DIOCHDIROFPRHY-UHFFFAOYSA-N 0.000 description 2
- CGXDOUGERIWXJK-UHFFFAOYSA-N NCCN(C1CCNCC1)C(c1cc(ccc(-c(cc2)ccc2F)c2)c2[nH]1)=O Chemical compound NCCN(C1CCNCC1)C(c1cc(ccc(-c(cc2)ccc2F)c2)c2[nH]1)=O CGXDOUGERIWXJK-UHFFFAOYSA-N 0.000 description 2
- YIMDEMGBMNRVFD-UHFFFAOYSA-N O=C(c1cc(ccc(-c(cc2)ccc2F)c2)c2[nH]1)NCCNC1CCNCC1 Chemical compound O=C(c1cc(ccc(-c(cc2)ccc2F)c2)c2[nH]1)NCCNC1CCNCC1 YIMDEMGBMNRVFD-UHFFFAOYSA-N 0.000 description 2
- YKUCAXOXIMAIBF-FQEVSTJZSA-N O=C(c1cc(ccc(-c(cc2)ccc2F)c2)c2[nH]1)N[C@@H](CC1)CN1C1CCNCC1 Chemical compound O=C(c1cc(ccc(-c(cc2)ccc2F)c2)c2[nH]1)N[C@@H](CC1)CN1C1CCNCC1 YKUCAXOXIMAIBF-FQEVSTJZSA-N 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 1
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 241000588626 Acinetobacter baumannii Species 0.000 description 1
- 241000588624 Acinetobacter calcoaceticus Species 0.000 description 1
- 241001148231 Acinetobacter haemolyticus Species 0.000 description 1
- 241001135518 Acinetobacter lwoffii Species 0.000 description 1
- 241000186046 Actinomyces Species 0.000 description 1
- 241000186044 Actinomyces viscosus Species 0.000 description 1
- 241000607528 Aeromonas hydrophila Species 0.000 description 1
- 241000589155 Agrobacterium tumefaciens Species 0.000 description 1
- 241000193738 Bacillus anthracis Species 0.000 description 1
- 241000193755 Bacillus cereus Species 0.000 description 1
- 244000063299 Bacillus subtilis Species 0.000 description 1
- 235000014469 Bacillus subtilis Nutrition 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000606125 Bacteroides Species 0.000 description 1
- 241001135322 Bacteroides eggerthii Species 0.000 description 1
- 241000606124 Bacteroides fragilis Species 0.000 description 1
- 241000606123 Bacteroides thetaiotaomicron Species 0.000 description 1
- 241000606219 Bacteroides uniformis Species 0.000 description 1
- 241000606215 Bacteroides vulgatus Species 0.000 description 1
- 241000588779 Bordetella bronchiseptica Species 0.000 description 1
- 241000588780 Bordetella parapertussis Species 0.000 description 1
- 241000588832 Bordetella pertussis Species 0.000 description 1
- 241000589969 Borreliella burgdorferi Species 0.000 description 1
- 241000589513 Burkholderia cepacia Species 0.000 description 1
- XJUVCQNWZFPCFI-UHFFFAOYSA-N CC(C)C(CCC(CNC(c1cc(cc(cc2)-c(cc3)ccc3F)c2[nH]1)=O)N)N Chemical compound CC(C)C(CCC(CNC(c1cc(cc(cc2)-c(cc3)ccc3F)c2[nH]1)=O)N)N XJUVCQNWZFPCFI-UHFFFAOYSA-N 0.000 description 1
- NIRWXOBKHSZLBP-RGURZIINSA-N CC(C)C(CC[C@@H](CNC(C)=O)N)N Chemical compound CC(C)C(CC[C@@H](CNC(C)=O)N)N NIRWXOBKHSZLBP-RGURZIINSA-N 0.000 description 1
- NHZCKVGXUAZDQJ-XJDOXCRVSA-N CC(C)C(CC[C@@H](CNC(c1cc(ccc(-c(cc2)ccc2F)c2)c2[nH]1)=O)N)N Chemical compound CC(C)C(CC[C@@H](CNC(c1cc(ccc(-c(cc2)ccc2F)c2)c2[nH]1)=O)N)N NHZCKVGXUAZDQJ-XJDOXCRVSA-N 0.000 description 1
- LBESCZBLSNDRMB-SSDOTTSWSA-N CC(NC[C@@H](CCCN)N)=O Chemical compound CC(NC[C@@H](CCCN)N)=O LBESCZBLSNDRMB-SSDOTTSWSA-N 0.000 description 1
- LBESCZBLSNDRMB-ZETCQYMHSA-N CC(NC[C@H](CCCN)N)=O Chemical compound CC(NC[C@H](CCCN)N)=O LBESCZBLSNDRMB-ZETCQYMHSA-N 0.000 description 1
- NWQKZNSGVLFRJY-LURJTMIESA-N CC(NC[C@H](CCN)N)=O Chemical compound CC(NC[C@H](CCN)N)=O NWQKZNSGVLFRJY-LURJTMIESA-N 0.000 description 1
- RCEQOBAYZNEIDY-SFYZADRCSA-N CC(NC[C@H]1NC[C@@H](CN)C1)=O Chemical compound CC(NC[C@H]1NC[C@@H](CN)C1)=O RCEQOBAYZNEIDY-SFYZADRCSA-N 0.000 description 1
- WYSLMGFLJILMSV-ZETCQYMHSA-N CCC(NC[C@H](CCCN)N)=O Chemical compound CCC(NC[C@H](CCCN)N)=O WYSLMGFLJILMSV-ZETCQYMHSA-N 0.000 description 1
- SZMGLIDITXXCEJ-INIZCTEOSA-N COc1cc(-c2cc([nH]c(C(NC[C@H](CCCN)N)=O)c3)c3cc2)ccc1F Chemical compound COc1cc(-c2cc([nH]c(C(NC[C@H](CCCN)N)=O)c3)c3cc2)ccc1F SZMGLIDITXXCEJ-INIZCTEOSA-N 0.000 description 1
- USWLQLQBVASTSA-SFHVURJKSA-N C[n]1c2cc(-c(cc3)ccc3F)ccc2cc1C(NC[C@H](CCCN)N)=O Chemical compound C[n]1c2cc(-c(cc3)ccc3F)ccc2cc1C(NC[C@H](CCCN)N)=O USWLQLQBVASTSA-SFHVURJKSA-N 0.000 description 1
- 241000589877 Campylobacter coli Species 0.000 description 1
- 241000589874 Campylobacter fetus Species 0.000 description 1
- 241000589875 Campylobacter jejuni Species 0.000 description 1
- 241000010804 Caulobacter vibrioides Species 0.000 description 1
- ZXWQLRHUDNPWHU-SFHVURJKSA-N Cc(cc1)ccc1-c1cc([nH]c(C(NC[C@H](CCCN)N)=O)c2)c2cc1 Chemical compound Cc(cc1)ccc1-c1cc([nH]c(C(NC[C@H](CCCN)N)=O)c2)c2cc1 ZXWQLRHUDNPWHU-SFHVURJKSA-N 0.000 description 1
- ULAKQXVWRWBVQO-KRWDZBQOSA-N Cc1c(C(NC[C@H](CCCN)N)=O)[nH]c(cc2)c1cc2-c(cc1)ccc1F Chemical compound Cc1c(C(NC[C@H](CCCN)N)=O)[nH]c(cc2)c1cc2-c(cc1)ccc1F ULAKQXVWRWBVQO-KRWDZBQOSA-N 0.000 description 1
- QPWVBIPXMXYUJH-KRWDZBQOSA-N Cc1c(C(NC[C@H](CCCN)N)=O)[nH]c2cc(-c(cc3)ccc3F)ccc12 Chemical compound Cc1c(C(NC[C@H](CCCN)N)=O)[nH]c2cc(-c(cc3)ccc3F)ccc12 QPWVBIPXMXYUJH-KRWDZBQOSA-N 0.000 description 1
- LAUGKOXNROYJMG-KDOFPFPSSA-N Cc1c(C(NC[C@H]2NC[C@@H](CN)C2)=O)[nH]c2cc(-c(cc3)ccc3F)ccc12 Chemical compound Cc1c(C(NC[C@H]2NC[C@@H](CN)C2)=O)[nH]c2cc(-c(cc3)ccc3F)ccc12 LAUGKOXNROYJMG-KDOFPFPSSA-N 0.000 description 1
- 241000606153 Chlamydia trachomatis Species 0.000 description 1
- 241000588919 Citrobacter freundii Species 0.000 description 1
- 241000588917 Citrobacter koseri Species 0.000 description 1
- 241000193163 Clostridioides difficile Species 0.000 description 1
- 241000186227 Corynebacterium diphtheriae Species 0.000 description 1
- 241000918600 Corynebacterium ulcerans Species 0.000 description 1
- 241001135265 Cronobacter sakazakii Species 0.000 description 1
- 241000186427 Cutibacterium acnes Species 0.000 description 1
- 241001600125 Delftia acidovorans Species 0.000 description 1
- 241000881810 Enterobacter asburiae Species 0.000 description 1
- 241000588697 Enterobacter cloacae Species 0.000 description 1
- 241000194032 Enterococcus faecalis Species 0.000 description 1
- 241000194031 Enterococcus faecium Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 241000605986 Fusobacterium nucleatum Species 0.000 description 1
- 241000207201 Gardnerella vaginalis Species 0.000 description 1
- 241000606788 Haemophilus haemolyticus Species 0.000 description 1
- 241000606768 Haemophilus influenzae Species 0.000 description 1
- 241000606822 Haemophilus parahaemolyticus Species 0.000 description 1
- 241000606766 Haemophilus parainfluenzae Species 0.000 description 1
- 241000590002 Helicobacter pylori Species 0.000 description 1
- 241000589015 Kingella denitrificans Species 0.000 description 1
- 241000589014 Kingella kingae Species 0.000 description 1
- 241000589012 Kingella oralis Species 0.000 description 1
- 241000588915 Klebsiella aerogenes Species 0.000 description 1
- 241000588749 Klebsiella oxytoca Species 0.000 description 1
- 241000588747 Klebsiella pneumoniae Species 0.000 description 1
- 241001534204 Klebsiella pneumoniae subsp. rhinoscleromatis Species 0.000 description 1
- 241000589242 Legionella pneumophila Species 0.000 description 1
- 241000186779 Listeria monocytogenes Species 0.000 description 1
- 241001293418 Mannheimia haemolytica Species 0.000 description 1
- 241000191938 Micrococcus luteus Species 0.000 description 1
- 241000588622 Moraxella bovis Species 0.000 description 1
- 241000588629 Moraxella lacunata Species 0.000 description 1
- 241000588772 Morganella morganii Species 0.000 description 1
- 241000186367 Mycobacterium avium Species 0.000 description 1
- 241000186364 Mycobacterium intracellulare Species 0.000 description 1
- 241000186362 Mycobacterium leprae Species 0.000 description 1
- 241000187479 Mycobacterium tuberculosis Species 0.000 description 1
- GZUGFQSOSDPRRI-UHFFFAOYSA-N NCCCC(CNC(c([n](Cc(cc1)ccc1F)c1c2)cc1ccc2-c(cc1)ccc1F)=O)N Chemical compound NCCCC(CNC(c([n](Cc(cc1)ccc1F)c1c2)cc1ccc2-c(cc1)ccc1F)=O)N GZUGFQSOSDPRRI-UHFFFAOYSA-N 0.000 description 1
- ZRCJAWNRQFRQKP-KRWDZBQOSA-N NCCC[C@@H](CNC(c([nH]c1c2)cc1ccc2-c(cc1)ccc1F)=O)N Chemical compound NCCC[C@@H](CNC(c([nH]c1c2)cc1ccc2-c(cc1)ccc1F)=O)N ZRCJAWNRQFRQKP-KRWDZBQOSA-N 0.000 description 1
- WEVBTTBNQKGBNP-HNNXBMFYSA-N NCCC[C@@H](CNC(c([nH]c1cc(-c(cc2)ccc2F)ccc11)c1F)=O)N Chemical compound NCCC[C@@H](CNC(c([nH]c1cc(-c(cc2)ccc2F)ccc11)c1F)=O)N WEVBTTBNQKGBNP-HNNXBMFYSA-N 0.000 description 1
- AZDUYUDXWBOUMD-HNNXBMFYSA-N NCCC[C@@H](CNC(c1cc(ccc(-c(c(Cl)c2)ccc2F)c2)c2[nH]1)=O)N Chemical compound NCCC[C@@H](CNC(c1cc(ccc(-c(c(Cl)c2)ccc2F)c2)c2[nH]1)=O)N AZDUYUDXWBOUMD-HNNXBMFYSA-N 0.000 description 1
- IMVVSWAHFLQPEP-INIZCTEOSA-N NCCC[C@@H](CNC(c1cc(ccc(-c(cc2)ccc2[N+]([O-])=O)c2)c2[nH]1)=O)N Chemical compound NCCC[C@@H](CNC(c1cc(ccc(-c(cc2)ccc2[N+]([O-])=O)c2)c2[nH]1)=O)N IMVVSWAHFLQPEP-INIZCTEOSA-N 0.000 description 1
- KGZWIXTWOCVJGY-KRWDZBQOSA-N NCCC[C@@H](CNC(c1cc(ccc(-c2cccc(F)c2)c2)c2[nH]1)=O)N Chemical compound NCCC[C@@H](CNC(c1cc(ccc(-c2cccc(F)c2)c2)c2[nH]1)=O)N KGZWIXTWOCVJGY-KRWDZBQOSA-N 0.000 description 1
- ZJFLJKCESJAYON-INIZCTEOSA-N NCCC[C@@H](CNC(c1cc2cccc(-c(cc3)ccc3F)c2[nH]1)=O)N Chemical compound NCCC[C@@H](CNC(c1cc2cccc(-c(cc3)ccc3F)c2[nH]1)=O)N ZJFLJKCESJAYON-INIZCTEOSA-N 0.000 description 1
- ZRCJAWNRQFRQKP-QGZVFWFLSA-N NCCC[C@H](CNC(c1cc(ccc(-c(cc2)ccc2F)c2)c2[nH]1)=O)N Chemical compound NCCC[C@H](CNC(c1cc(ccc(-c(cc2)ccc2F)c2)c2[nH]1)=O)N ZRCJAWNRQFRQKP-QGZVFWFLSA-N 0.000 description 1
- NOXOYPSTKJVENR-INIZCTEOSA-N NCC[C@@H](CNC(c1cc(ccc(-c(cc2)ccc2F)c2)c2[nH]1)=O)N Chemical compound NCC[C@@H](CNC(c1cc(ccc(-c(cc2)ccc2F)c2)c2[nH]1)=O)N NOXOYPSTKJVENR-INIZCTEOSA-N 0.000 description 1
- LLMXOOJGLBAXRX-ACJLOTCBSA-N NC[C@@H]1CN[C@H](CNC(c2cc(ccc(-c(cc3)ccc3F)c3)c3[nH]2)=O)C1 Chemical compound NC[C@@H]1CN[C@H](CNC(c2cc(ccc(-c(cc3)ccc3F)c3)c3[nH]2)=O)C1 LLMXOOJGLBAXRX-ACJLOTCBSA-N 0.000 description 1
- 241000588652 Neisseria gonorrhoeae Species 0.000 description 1
- 241000588650 Neisseria meningitidis Species 0.000 description 1
- 241001135232 Odoribacter splanchnicus Species 0.000 description 1
- 241000588912 Pantoea agglomerans Species 0.000 description 1
- 241000606210 Parabacteroides distasonis Species 0.000 description 1
- 241000606598 Pasteurella canis Species 0.000 description 1
- 241000606856 Pasteurella multocida Species 0.000 description 1
- 241000605862 Porphyromonas gingivalis Species 0.000 description 1
- 241000588770 Proteus mirabilis Species 0.000 description 1
- 241000588767 Proteus vulgaris Species 0.000 description 1
- 241000576783 Providencia alcalifaciens Species 0.000 description 1
- 241000588777 Providencia rettgeri Species 0.000 description 1
- 241000588778 Providencia stuartii Species 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- 241000168225 Pseudomonas alcaligenes Species 0.000 description 1
- 241000589540 Pseudomonas fluorescens Species 0.000 description 1
- 241000589776 Pseudomonas putida Species 0.000 description 1
- 241001354013 Salmonella enterica subsp. enterica serovar Enteritidis Species 0.000 description 1
- 241000531795 Salmonella enterica subsp. enterica serovar Paratyphi A Species 0.000 description 1
- 241000293871 Salmonella enterica subsp. enterica serovar Typhi Species 0.000 description 1
- 241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 description 1
- 241000607715 Serratia marcescens Species 0.000 description 1
- 241000607768 Shigella Species 0.000 description 1
- 241000607764 Shigella dysenteriae Species 0.000 description 1
- 241000607760 Shigella sonnei Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 241000191963 Staphylococcus epidermidis Species 0.000 description 1
- 241000191984 Staphylococcus haemolyticus Species 0.000 description 1
- 241000192087 Staphylococcus hominis Species 0.000 description 1
- 241000191982 Staphylococcus hyicus Species 0.000 description 1
- 241000191980 Staphylococcus intermedius Species 0.000 description 1
- 241001464905 Staphylococcus saccharolyticus Species 0.000 description 1
- 241001147691 Staphylococcus saprophyticus Species 0.000 description 1
- 241000122971 Stenotrophomonas Species 0.000 description 1
- 241000193985 Streptococcus agalactiae Species 0.000 description 1
- 241000194019 Streptococcus mutans Species 0.000 description 1
- 241000193998 Streptococcus pneumoniae Species 0.000 description 1
- 241000193996 Streptococcus pyogenes Species 0.000 description 1
- 241000194024 Streptococcus salivarius Species 0.000 description 1
- 241000194023 Streptococcus sanguinis Species 0.000 description 1
- 241000722072 Suttonella indologenes Species 0.000 description 1
- 241001135235 Tannerella forsythia Species 0.000 description 1
- 241001148135 Veillonella parvula Species 0.000 description 1
- 241000607626 Vibrio cholerae Species 0.000 description 1
- 241000607272 Vibrio parahaemolyticus Species 0.000 description 1
- 241000607734 Yersinia <bacteria> Species 0.000 description 1
- 241000607447 Yersinia enterocolitica Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 241000607477 Yersinia pseudotuberculosis Species 0.000 description 1
- 241000606834 [Haemophilus] ducreyi Species 0.000 description 1
- 229940065181 bacillus anthracis Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 229940038705 chlamydia trachomatis Drugs 0.000 description 1
- 229940092559 enterobacter aerogenes Drugs 0.000 description 1
- 229940032049 enterococcus faecalis Drugs 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 229940118764 francisella tularensis Drugs 0.000 description 1
- 229940047650 haemophilus influenzae Drugs 0.000 description 1
- 229940037467 helicobacter pylori Drugs 0.000 description 1
- 229940115932 legionella pneumophila Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229940076266 morganella morganii Drugs 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 229940051027 pasteurella multocida Drugs 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 229940055019 propionibacterium acne Drugs 0.000 description 1
- 229940007042 proteus vulgaris Drugs 0.000 description 1
- 229940007046 shigella dysenteriae Drugs 0.000 description 1
- 229940115939 shigella sonnei Drugs 0.000 description 1
- 229940037649 staphylococcus haemolyticus Drugs 0.000 description 1
- 229940031000 streptococcus pneumoniae Drugs 0.000 description 1
- 229940118696 vibrio cholerae Drugs 0.000 description 1
- 229940098232 yersinia enterocolitica Drugs 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762469987P | 2017-03-10 | 2017-03-10 | |
| US62/469,987 | 2017-03-10 | ||
| US201762523154P | 2017-06-21 | 2017-06-21 | |
| US62/523,154 | 2017-06-21 | ||
| PCT/US2018/021848 WO2018165611A1 (en) | 2017-03-10 | 2018-03-09 | Indole derivatives as efflux pump inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020510044A JP2020510044A (ja) | 2020-04-02 |
| JP2020510044A5 true JP2020510044A5 (https=) | 2021-04-15 |
| JP7323179B2 JP7323179B2 (ja) | 2023-08-08 |
Family
ID=62044950
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019549454A Active JP7323179B2 (ja) | 2017-03-10 | 2018-03-09 | 排出ポンプ阻害剤としてのインドール誘導体 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US11993571B2 (https=) |
| EP (1) | EP3592736A1 (https=) |
| JP (1) | JP7323179B2 (https=) |
| KR (1) | KR102697360B1 (https=) |
| CN (1) | CN110770224B (https=) |
| AU (1) | AU2018231120B2 (https=) |
| BR (1) | BR112019018691A2 (https=) |
| CA (1) | CA3061238A1 (https=) |
| IL (1) | IL269210B2 (https=) |
| MX (1) | MX2019010717A (https=) |
| SG (1) | SG11201908351TA (https=) |
| WO (1) | WO2018165611A1 (https=) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10556854B2 (en) | 2016-02-24 | 2020-02-11 | Rutgers, The State University Of New Jersey | Bacterial efflux pump inhibitors |
| WO2017147335A1 (en) | 2016-02-24 | 2017-08-31 | Rutgers, The State University Of New Jersey | Bacterial efflux pump inhibitors |
| SG11201908351TA (en) | 2017-03-10 | 2019-10-30 | Edmond J Lavoie | Indole derivatives as efflux pump inhibitors |
| US11938114B2 (en) | 2017-03-10 | 2024-03-26 | Rutgers, The State University Of New Jersey | Bacterial efflux pump inhibitors |
| WO2018165612A1 (en) | 2017-03-10 | 2018-09-13 | Rutgers, The State University Of New Jersey | Bacterial efflux pump inhibitors |
| EP3630109A4 (en) | 2017-05-26 | 2021-03-17 | Rutgers, the State University of New Jersey | BACTERIAL EFFLUX PUMP INHIBITORS |
| WO2019005841A1 (en) | 2017-06-26 | 2019-01-03 | Rutgers, The State University Of New Jersey | THERAPEUTIC COMPOUNDS AND METHODS FOR TREATING INFECTION |
| WO2019099402A1 (en) * | 2017-11-14 | 2019-05-23 | Rutgers, The State University Of New Jersey | Therapeutic compounds and methods to treat infection |
| KR102704123B1 (ko) | 2019-11-01 | 2024-09-06 | 에스엘 주식회사 | 차량용 램프 |
| WO2025043115A1 (en) | 2023-08-23 | 2025-02-27 | Taxis Pharmaceuticals, Inc. | Bacterial efflux pump inhibitors |
| AU2024332661A1 (en) * | 2023-08-29 | 2026-04-09 | Maze Therapeutics, Inc. | Inhibitors of solute carrier family 6a member 19 (slc6a19) and methods of use thereof |
Family Cites Families (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3238215A (en) * | 1963-10-17 | 1966-03-01 | Sterling Drug Inc | 1-[(3-, 2-, and 1-indolyl)-lower-alkyl-, lower-alkenyl-, and lower-alkynyl]piperidines |
| US3465080A (en) * | 1968-10-07 | 1969-09-02 | American Cyanamid Co | Therapeutic compositions containing morpholinoalkylene - indoles and methods of administering such in the treatment of depression |
| US3978224A (en) | 1975-07-01 | 1976-08-31 | Schering Corporation | Antimicrobial halo-substituted-2-cyanoethylaminoalkyl-3-phenyl-indoles |
| US4910193A (en) * | 1985-12-16 | 1990-03-20 | Sandoz Ltd. | Treatment of gastrointestinal disorders |
| US4938949A (en) | 1988-09-12 | 1990-07-03 | University Of New York | Treatment of damaged bone marrow and dosage units therefor |
| WO1992004017A1 (en) | 1990-09-10 | 1992-03-19 | The Upjohn Company | Cis-n-(2-aminocyclohexyl)benzamide and their enantiomers as anticonvulsants |
| US5864039A (en) * | 1994-03-30 | 1999-01-26 | Yoshitomi Pharmaceutical Industries, Ltd. | Benzoic acid compounds and use thereof as medicaments |
| US5663152A (en) | 1995-01-19 | 1997-09-02 | Asahi Kasei Kogyo Kabushiki Kaisha | Potentiators for aminoglycosides |
| US6506339B1 (en) * | 1997-02-10 | 2003-01-14 | Biomedical Design, Inc. | Method of sterilization |
| WO1999037667A1 (en) * | 1998-01-23 | 1999-07-29 | Microcide Pharmaceuticals, Inc. | Efflux pump inhibitors |
| US6204279B1 (en) | 1998-06-03 | 2001-03-20 | Microcide Pharmaceuticals, Inc. | Peptidomimetic efflux pump inhibitors |
| US6326391B1 (en) | 1998-12-04 | 2001-12-04 | Influx, Inc. | Inhibitors of multidrug transporters |
| US6730684B1 (en) * | 1999-10-08 | 2004-05-04 | Affinium Pharmaceuticals, Inc. | Fab I inhibitors |
| WO2001026652A1 (en) | 1999-10-08 | 2001-04-19 | Smithkline Beecham Corporation | Fab i inhibitors |
| US6555569B2 (en) | 2000-03-07 | 2003-04-29 | Pfizer Inc. | Use of heteroaryl substituted N-(indole-2-carbonyl-) amides for treatment of infection |
| WO2011101710A1 (en) | 2010-02-16 | 2011-08-25 | Wockhardt Research Centre | Efflux pump inhibitors |
| WO2003000657A1 (en) | 2001-06-20 | 2003-01-03 | Daiichi Pharmaceutical Co., Ltd. | Diamine derivatives |
| HUP0103986A2 (hu) * | 2001-09-28 | 2003-06-28 | Richter Gedeon Vegyészeti Gyár Rt. | Új karbonsavamid szerkezetet tartalmazó piperidinil vegyületek, eljárás az előállításukra és ezeket tartalmazó gyógyszerkészítmények |
| EP1314733A1 (en) * | 2001-11-22 | 2003-05-28 | Aventis Pharma Deutschland GmbH | Indole-2-carboxamides as factor Xa inhibitors |
| WO2004062674A2 (en) | 2003-01-07 | 2004-07-29 | Paratek Pharmaceuticals, Inc. | Substituted polyamines as inhibitors of bacterial efflux pumps |
| GB0403038D0 (en) * | 2004-02-11 | 2004-03-17 | Novartis Ag | Organic compounds |
| US7994225B2 (en) | 2004-03-17 | 2011-08-09 | Rempex Pharmaceuticals, Inc. | Bacterial efflux pump inhibitors for the treatment of ophthalmic and otic infections |
| EP1758920A1 (en) | 2004-05-21 | 2007-03-07 | Mpex Pharmaceuticals, Inc. | Bacterial efflux pump inhibitors and methods of treating bacterial infections |
| WO2006058088A2 (en) | 2004-11-23 | 2006-06-01 | Ptc Therapeutics, Inc. | Carbazole, carboline and indole derivatives useful in the inhibition of vegf production |
| US7855228B2 (en) | 2005-02-10 | 2010-12-21 | The Board Of Trustees Of The Leland Stamford Junior University | Antibiotics targeting MreB |
| WO2007115231A2 (en) * | 2006-03-30 | 2007-10-11 | Chemocentryx, Inc. | Cxcr4 modulators |
| FR2904317A1 (fr) * | 2006-07-27 | 2008-02-01 | Inst Nat Sante Rech Med | Analogues d'halogenobenzamides marques a titre de radiopharmaceutiques |
| CA2927045A1 (en) | 2006-10-03 | 2008-04-10 | Muthiah Manoharan | Lipid containing formulations |
| AR070398A1 (es) * | 2008-02-22 | 2010-03-31 | Gruenenthal Chemie | Derivados sustituidos de indol |
| WO2009110002A1 (en) | 2008-03-05 | 2009-09-11 | Council Of Scientific & Industrial Research | Novel efflux pump inhibitors |
| JP5608655B2 (ja) | 2008-09-18 | 2014-10-15 | エヴォテック アーゲー | Ｐ２ｘ３受容体活性のモジュレーター |
| WO2010115184A2 (en) | 2009-04-03 | 2010-10-07 | Achillion Pharmaceuticals, Inc. | Hydroxythienoquinolones and related compounds as anti-infective agents |
| EP2394653A1 (en) * | 2010-05-26 | 2011-12-14 | Almirall, S.A. | Topical pharmaceutical compositions comprising mometasone furoate |
| FR2969150B1 (fr) * | 2010-12-20 | 2013-07-26 | Centre Nat Rech Scient | Nouvelles molecules indoliques demontrant des activites antibacteriennes dans une variete de bacteries a gram-negatif et positif dont des bacteries multidrogues-resistantes |
| ES2660210T3 (es) | 2012-09-07 | 2018-03-21 | Novartis Ag | Derivados de indolcarboxamida y usos de los mismos |
| WO2014078294A1 (en) * | 2012-11-13 | 2014-05-22 | Memorial Sloan-Kettering Cancer Center | Indole compounds and their use as antimicrobials |
| WO2015164482A1 (en) * | 2014-04-22 | 2015-10-29 | The Johns Hopkins University | Inhibitors of drug-resistant mycobacterium tuberculosis |
| BR112017004612A2 (pt) | 2014-09-10 | 2018-01-30 | Epizyme, Inc. | compostos, composição farmacêutica, usos de um composto, e kit |
| US9926261B2 (en) | 2015-03-10 | 2018-03-27 | Rutgers, The State University Of New Jersey | Bacterial efflux pump inhibitors |
| US9950993B2 (en) | 2015-03-13 | 2018-04-24 | Rutgers, The State University Of New Jersey | Bacterial efflux pump inhibitors |
| CN107709314A (zh) | 2015-06-11 | 2018-02-16 | 巴斯利尔药物国际股份公司 | 外排泵抑制剂及其治疗性用途 |
| WO2017023894A1 (en) * | 2015-08-03 | 2017-02-09 | Raze Therapeutics, Inc. | Mthfd2 inhibitors and uses thereof |
| WO2017147335A1 (en) | 2016-02-24 | 2017-08-31 | Rutgers, The State University Of New Jersey | Bacterial efflux pump inhibitors |
| US10556854B2 (en) | 2016-02-24 | 2020-02-11 | Rutgers, The State University Of New Jersey | Bacterial efflux pump inhibitors |
| CA3047404A1 (en) | 2016-12-23 | 2018-06-28 | Aquinnah Pharmaceuticals, Inc. | Compounds, compositions and methods of use |
| SG11201908351TA (en) | 2017-03-10 | 2019-10-30 | Edmond J Lavoie | Indole derivatives as efflux pump inhibitors |
| US11938114B2 (en) | 2017-03-10 | 2024-03-26 | Rutgers, The State University Of New Jersey | Bacterial efflux pump inhibitors |
| WO2018165612A1 (en) | 2017-03-10 | 2018-09-13 | Rutgers, The State University Of New Jersey | Bacterial efflux pump inhibitors |
| EP3630109A4 (en) | 2017-05-26 | 2021-03-17 | Rutgers, the State University of New Jersey | BACTERIAL EFFLUX PUMP INHIBITORS |
| WO2019005841A1 (en) | 2017-06-26 | 2019-01-03 | Rutgers, The State University Of New Jersey | THERAPEUTIC COMPOUNDS AND METHODS FOR TREATING INFECTION |
| US20190031624A1 (en) | 2017-07-28 | 2019-01-31 | Rutgers, The State University Of New Jersey | Therapeutic compounds and methods to treat infection |
| WO2019099402A1 (en) * | 2017-11-14 | 2019-05-23 | Rutgers, The State University Of New Jersey | Therapeutic compounds and methods to treat infection |
-
2018
- 2018-03-09 SG SG11201908351T patent/SG11201908351TA/en unknown
- 2018-03-09 KR KR1020197029528A patent/KR102697360B1/ko active Active
- 2018-03-09 BR BR112019018691-3A patent/BR112019018691A2/pt active Search and Examination
- 2018-03-09 EP EP18719686.0A patent/EP3592736A1/en active Pending
- 2018-03-09 CA CA3061238A patent/CA3061238A1/en active Pending
- 2018-03-09 MX MX2019010717A patent/MX2019010717A/es unknown
- 2018-03-09 WO PCT/US2018/021848 patent/WO2018165611A1/en not_active Ceased
- 2018-03-09 CN CN201880030845.1A patent/CN110770224B/zh active Active
- 2018-03-09 IL IL269210A patent/IL269210B2/en unknown
- 2018-03-09 JP JP2019549454A patent/JP7323179B2/ja active Active
- 2018-03-09 US US16/492,901 patent/US11993571B2/en active Active
- 2018-03-09 AU AU2018231120A patent/AU2018231120B2/en active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2020510044A5 (https=) | ||
| JP2020527597A5 (https=) | ||
| CA2504448A1 (en) | Transcription factor modulating compounds and methods of use thereof | |
| FI3651766T3 (fi) | 4-(4-(4-(((2-(2,6-dioksopiperidin-3-yyli)-l-oksoisoindolin-4-yyli)oksi)metyyli)bentsyyli)piperatsin-1-yyli)-3-fluoribentsonitriili antiproliferatiivisena yhdisteenä | |
| JP2017517567A5 (https=) | ||
| JP7323179B2 (ja) | 排出ポンプ阻害剤としてのインドール誘導体 | |
| JP5852007B2 (ja) | 抗微生物剤の増進剤としてのカルコン類 | |
| FI3986419T3 (fi) | Boorihappojohdannaisia ja niiden terapeuttisia käyttöjä | |
| RU2013104951A (ru) | Циклические бороновые кислотно-эфирные производные и их использование в терапии | |
| SI2344129T1 (en) | AEROSOL FLUOROKINOLONAL FORMULATIONS FOR IMPROVED PHARMACOKINETICS | |
| JP2009541332A5 (https=) | ||
| RU2018122505A (ru) | Макроциклические антибиотики широкого спектра действия | |
| JP2021522167A5 (https=) | ||
| JP2016517851A5 (https=) | ||
| FI4121058T3 (fi) | Oksatsolidinoniyhdiste ja sen käyttö antibakteerisena aineena | |
| RU2016107436A (ru) | Линейные пептидные антибиотики | |
| JP2001503411A (ja) | 抗生物質耐性感染症の処置のための化合物、組成物および方法 | |
| JP2016528257A5 (https=) | ||
| US20190031624A1 (en) | Therapeutic compounds and methods to treat infection | |
| JP2016501864A5 (https=) | ||
| WO2004062674A2 (en) | Substituted polyamines as inhibitors of bacterial efflux pumps | |
| RU2018122498A (ru) | Макроциклические антибиотики широкого спектра действия | |
| CA2768582A1 (en) | Spectinamides as anti-tuberculosis agents | |
| CN1268135A (zh) | 螺杆菌属感染引起的疾病的预防/治疗剂 | |
| Vaghela et al. | Comparison of safety and analgesic efficacy of diclofenac sodium with etodolac after surgical extraction of third molars: a randomized, double-blind, double-dummy, parallel-group study |