JP2020510044A5 - - Google Patents
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- 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
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- 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
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- 241000589602 Francisella tularensis Species 0.000 description 2
- 241000588655 Moraxella catarrhalis Species 0.000 description 2
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- 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
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- 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
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- 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
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- 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
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- 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
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- 125000001153 fluoro group Chemical group F* 0.000 description 1
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- 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
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- 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 |
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| EP (1) | EP3592736A1 (https=) |
| JP (1) | JP7323179B2 (https=) |
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| US10836706B2 (en) | 2016-02-24 | 2020-11-17 | 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 |
| 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 |
| CN110770224B (zh) | 2017-03-10 | 2022-11-18 | 罗格斯新泽西州立大学 | 作为外排泵抑制剂的吲哚衍生物 |
| 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 |
| US11845742B2 (en) | 2017-11-14 | 2023-12-19 | 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 |
| AU2024327693A1 (en) | 2023-08-23 | 2026-04-02 | Taxis Pharmaceuticals, Inc. | Bacterial efflux pump inhibitors |
| TW202525791A (zh) * | 2023-08-29 | 2025-07-01 | 美商梅斯治療股份有限公司 | 溶質載體家族６ａ成員１９（ｓｌｃ６ａ１９）之抑制劑及其使用方法 |
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| US11938114B2 (en) | 2017-03-10 | 2024-03-26 | Rutgers, The State University Of New Jersey | Bacterial efflux pump inhibitors |
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| 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 |
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-
2018
- 2018-03-09 CN CN201880030845.1A patent/CN110770224B/zh active Active
- 2018-03-09 BR BR112019018691-3A patent/BR112019018691A2/pt active Search and Examination
- 2018-03-09 WO PCT/US2018/021848 patent/WO2018165611A1/en not_active Ceased
- 2018-03-09 AU AU2018231120A patent/AU2018231120B2/en active Active
- 2018-03-09 KR KR1020197029528A patent/KR102697360B1/ko active Active
- 2018-03-09 MX MX2019010717A patent/MX2019010717A/es unknown
- 2018-03-09 SG SG11201908351T patent/SG11201908351TA/en unknown
- 2018-03-09 EP EP18719686.0A patent/EP3592736A1/en active Pending
- 2018-03-09 US US16/492,901 patent/US11993571B2/en active Active
- 2018-03-09 JP JP2019549454A patent/JP7323179B2/ja active Active
- 2018-03-09 CA CA3061238A patent/CA3061238A1/en active Pending
- 2018-03-09 IL IL269210A patent/IL269210B2/en unknown
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