JP2009518399A5 - - Google Patents
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- JP2009518399A5 JP2009518399A5 JP2008544384A JP2008544384A JP2009518399A5 JP 2009518399 A5 JP2009518399 A5 JP 2009518399A5 JP 2008544384 A JP2008544384 A JP 2008544384A JP 2008544384 A JP2008544384 A JP 2008544384A JP 2009518399 A5 JP2009518399 A5 JP 2009518399A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- acrylamide
- oxo
- pyrido
- dihydro
- 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.)
- Pending
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- 150000001875 compounds Chemical class 0.000 claims 37
- -1 6-Acetylamino-5-hydroxy-pyridin-3-yl Chemical group 0.000 claims 30
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims 15
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 5
- 125000005842 heteroatom Chemical group 0.000 claims 4
- GDFIQPPSGCKCEK-UHFFFAOYSA-N prop-2-enamide;2,2,2-trifluoroacetic acid Chemical compound NC(=O)C=C.OC(=O)C(F)(F)F GDFIQPPSGCKCEK-UHFFFAOYSA-N 0.000 claims 4
- FJWSMXKFXFFEPV-UHFFFAOYSA-N prop-2-enamide;hydrochloride Chemical compound Cl.NC(=O)C=C FJWSMXKFXFFEPV-UHFFFAOYSA-N 0.000 claims 4
- 125000004429 atom Chemical group 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
- ONKQGXQUAJXPHR-AYJWMTRPSA-N (e)-3-(2,2-dimethyl-3-oxo-4h-pyrido[3,2-b][1,4]oxazin-7-yl)-n-[(1r)-1-(3-ethyl-1-benzofuran-2-yl)ethyl]-n-methylprop-2-enamide Chemical compound N1C(=O)C(C)(C)OC2=CC(/C=C/C(=O)N(C)[C@H](C)C3=C(C4=CC=CC=C4O3)CC)=CN=C21 ONKQGXQUAJXPHR-AYJWMTRPSA-N 0.000 claims 1
- OGPQDGUEPUIDQC-MDZDMXLPSA-N (e)-3-(3-amino-2,2-dimethylpyrido[3,2-b][1,4]oxazin-7-yl)-n-methyl-n-[(3-methyl-1-benzofuran-2-yl)methyl]prop-2-enamide Chemical compound N1C(=N)C(C)(C)OC2=CC(/C=C/C(=O)N(CC3=C(C4=CC=CC=C4O3)C)C)=CN=C21 OGPQDGUEPUIDQC-MDZDMXLPSA-N 0.000 claims 1
- ALWKZANDFLJGME-TYYBGVCCSA-N (e)-3-(4-oxo-1,2,3,5-tetrahydropyrido[2,3-b][1,4]diazepin-8-yl)prop-2-enoic acid;hydrochloride Chemical compound Cl.N1C(=O)CCNC2=CC(/C=C/C(=O)O)=CN=C21 ALWKZANDFLJGME-TYYBGVCCSA-N 0.000 claims 1
- BOBBZVXOLZDIBF-MDZDMXLPSA-N (e)-3-(5-hydroxy-6,6-dimethyl-7-oxo-5,8-dihydro-1,8-naphthyridin-3-yl)-n-methyl-n-[(3-methyl-1-benzofuran-2-yl)methyl]prop-2-enamide Chemical compound N1C(=O)C(C)(C)C(O)C2=CC(/C=C/C(=O)N(CC3=C(C4=CC=CC=C4O3)C)C)=CN=C21 BOBBZVXOLZDIBF-MDZDMXLPSA-N 0.000 claims 1
- ALUQZCDDMSOJCV-MDZDMXLPSA-N (e)-3-(5-hydroxy-7-oxo-6-propan-2-yl-8h-1,8-naphthyridin-3-yl)-n-methyl-n-[(3-methyl-1-benzofuran-2-yl)methyl]prop-2-enamide Chemical compound O1C2=CC=CC=C2C(C)=C1CN(C)C(=O)/C=C/C1=CN=C(NC(C(C(C)C)=C2O)=O)C2=C1 ALUQZCDDMSOJCV-MDZDMXLPSA-N 0.000 claims 1
- LHHOUFUKOIEGAK-RRABGKBLSA-N (e)-3-(6-acetamido-5-hydroxypyridin-3-yl)-n-[(3-methoxy-2-propoxyphenyl)methyl]-n-methylprop-2-enamide;hydrochloride Chemical compound Cl.C1=CC=C(OC)C(OCCC)=C1CN(C)C(=O)\C=C\C1=CN=C(NC(C)=O)C(O)=C1 LHHOUFUKOIEGAK-RRABGKBLSA-N 0.000 claims 1
- URZRGDYEMPNNET-OUKQBFOZSA-N (e)-3-(6-amino-5-phenylmethoxypyridin-3-yl)-n-methyl-n-[(3-methyl-1-benzofuran-2-yl)methyl]prop-2-enamide Chemical compound O1C2=CC=CC=C2C(C)=C1CN(C)C(=O)\C=C\C(C=1)=CN=C(N)C=1OCC1=CC=CC=C1 URZRGDYEMPNNET-OUKQBFOZSA-N 0.000 claims 1
- KMFSKNKVMPXULQ-IEZBTEQYSA-N (e)-3-(6-aminopyridin-3-yl)-n-[(1r)-1-(3-ethyl-1-benzofuran-2-yl)ethyl]-n-methylprop-2-enamide Chemical compound CN([C@H](C)C1=C(C2=CC=CC=C2O1)CC)C(=O)\C=C\C1=CC=C(N)N=C1 KMFSKNKVMPXULQ-IEZBTEQYSA-N 0.000 claims 1
- BFEJTYGIEAOXFN-ASTDGNLGSA-N (e)-3-[2,2-dimethyl-3-(methylamino)pyrido[3,2-b][1,4]oxazin-7-yl]-n-methyl-n-[(3-methyl-1-benzofuran-2-yl)methyl]prop-2-enamide;hydrochloride Chemical compound Cl.O1C2=CC=CC=C2C(C)=C1CN(C)C(=O)/C=C/C1=CN=C2N/C(=N/C)C(C)(C)OC2=C1 BFEJTYGIEAOXFN-ASTDGNLGSA-N 0.000 claims 1
- JLHKDYJQOZUARQ-ZHACJKMWSA-N (e)-3-[2,2-dimethyl-3-(methylamino)pyrido[3,2-b][1,4]oxazin-7-yl]-n-methyl-n-[(3-methyl-1-benzothiophen-2-yl)methyl]prop-2-enamide Chemical compound S1C2=CC=CC=C2C(C)=C1CN(C)C(=O)/C=C/C1=CN=C2N/C(=N/C)C(C)(C)OC2=C1 JLHKDYJQOZUARQ-ZHACJKMWSA-N 0.000 claims 1
- XWWNDAHDJKPNIN-ZHACJKMWSA-N (e)-3-[6-amino-5-(pyridin-2-ylmethoxy)pyridin-3-yl]-n-methyl-n-[(3-methyl-1-benzofuran-2-yl)methyl]prop-2-enamide Chemical compound O1C2=CC=CC=C2C(C)=C1CN(C)C(=O)\C=C\C(C=1)=CN=C(N)C=1OCC1=CC=CC=N1 XWWNDAHDJKPNIN-ZHACJKMWSA-N 0.000 claims 1
- AYRUXHHHKFHBCY-MDZDMXLPSA-N (e)-3-[6-amino-5-(pyridin-3-ylmethoxy)pyridin-3-yl]-n-methyl-n-[(3-methyl-1-benzofuran-2-yl)methyl]prop-2-enamide Chemical compound O1C2=CC=CC=C2C(C)=C1CN(C)C(=O)\C=C\C(C=1)=CN=C(N)C=1OCC1=CC=CN=C1 AYRUXHHHKFHBCY-MDZDMXLPSA-N 0.000 claims 1
- HSBHNIOHJODSGR-KPKJPENVSA-N (e)-n-(1,2-dihydroacenaphthylen-5-ylmethyl)-3-(5-hydroxy-7-oxo-6-propan-2-yl-8h-1,8-naphthyridin-3-yl)-n-methylprop-2-enamide Chemical compound C1CC2=CC=CC3=C2C1=CC=C3CN(C)C(=O)/C=C/C1=CN=C(NC(C(C(C)C)=C2O)=O)C2=C1 HSBHNIOHJODSGR-KPKJPENVSA-N 0.000 claims 1
- OAEIEFOPFGGAPK-CMDGGOBGSA-N (e)-n-[(1,3-dimethylindol-2-yl)methyl]-n-methyl-3-(2-oxo-1,3,4,5-tetrahydropyrido[2,3-b][1,4]diazepin-8-yl)prop-2-enamide Chemical compound N1CCC(=O)NC2=CC(/C=C/C(=O)N(CC=3N(C4=CC=CC=C4C=3C)C)C)=CN=C21 OAEIEFOPFGGAPK-CMDGGOBGSA-N 0.000 claims 1
- VIVGMQKXNPBMAH-CMDGGOBGSA-N (e)-n-[(1,3-dimethylindol-2-yl)methyl]-n-methyl-3-(3-oxo-4h-pyrido[3,2-b][1,4]oxazin-7-yl)prop-2-enamide Chemical compound N1C(=O)COC2=CC(/C=C/C(=O)N(CC=3N(C4=CC=CC=C4C=3C)C)C)=CN=C21 VIVGMQKXNPBMAH-CMDGGOBGSA-N 0.000 claims 1
- NAZCCBMUGDDHCB-CMDGGOBGSA-N (e)-n-[(2-ethoxy-3-methoxyphenyl)methyl]-3-(5-hydroxy-7-oxo-8h-1,8-naphthyridin-3-yl)-n-methylprop-2-enamide Chemical compound C1=CC=C(OC)C(OCC)=C1CN(C)C(=O)\C=C\C1=CN=C(NC(=O)C=C2O)C2=C1 NAZCCBMUGDDHCB-CMDGGOBGSA-N 0.000 claims 1
- IGGOOUBXAXVWAZ-VOTSOKGWSA-N (e)-n-[(3,6-dimethyl-1h-indol-5-yl)methyl]-n-methyl-3-(3-oxo-4h-pyrido[3,2-b][1,4]oxazin-2-yl)prop-2-enamide Chemical compound O1C2=CC=CN=C2NC(=O)C1/C=C/C(=O)N(C)CC(C(=C1)C)=CC2=C1NC=C2C IGGOOUBXAXVWAZ-VOTSOKGWSA-N 0.000 claims 1
- UTQGNSXZSCNDRK-BQYQJAHWSA-N (e)-n-[(3,7-dimethyl-1h-indol-2-yl)methyl]-n-methyl-3-(3-oxo-4h-pyrido[3,2-b][1,4]oxazin-7-yl)prop-2-enamide Chemical compound N1C(=O)COC2=CC(/C=C/C(=O)N(CC3=C(C4=CC=CC(C)=C4N3)C)C)=CN=C21 UTQGNSXZSCNDRK-BQYQJAHWSA-N 0.000 claims 1
- PUPHTZOSRKLTNQ-VOTSOKGWSA-N (e)-n-[(3-chloro-1-benzofuran-2-yl)methyl]-n-methyl-3-(3-oxo-4h-pyrido[3,2-b][1,4]oxazin-7-yl)prop-2-enamide Chemical compound N1C(=O)COC2=CC(/C=C/C(=O)N(CC3=C(C4=CC=CC=C4O3)Cl)C)=CN=C21 PUPHTZOSRKLTNQ-VOTSOKGWSA-N 0.000 claims 1
- FJRPPXSHTBVUNC-CMDGGOBGSA-N (e)-n-methyl-3-(3-oxo-4h-pyrido[3,2-b][1,4]oxazin-7-yl)-n-[(3-propan-2-yl-1-benzofuran-2-yl)methyl]prop-2-enamide Chemical compound O1C2=CC=CC=C2C(C(C)C)=C1CN(C)C(=O)\C=C\C1=CN=C(NC(=O)CO2)C2=C1 FJRPPXSHTBVUNC-CMDGGOBGSA-N 0.000 claims 1
- KRLIUPZXWVAMSP-KUCQQTCKSA-N (e)-n-methyl-n-[(1r)-1-(3-methyl-1-benzothiophen-2-yl)ethyl]-3-(7-oxo-6,8-dihydro-5h-1,8-naphthyridin-3-yl)prop-2-enamide Chemical compound S1C2=CC=CC=C2C(C)=C1[C@@H](C)N(C)C(=O)\C=C\C1=CN=C(NC(=O)CC2)C2=C1 KRLIUPZXWVAMSP-KUCQQTCKSA-N 0.000 claims 1
- FFCIEWRQYRCHLO-BQYQJAHWSA-N (e)-n-methyl-n-[(3-methyl-1-benzofuran-2-yl)methyl]-3-(2-oxo-1,5-dihydropyrido[2,3-e][1,4]oxazepin-7-yl)prop-2-enamide Chemical compound N1C(=O)COCC2=CC(/C=C/C(=O)N(CC3=C(C4=CC=CC=C4O3)C)C)=CN=C21 FFCIEWRQYRCHLO-BQYQJAHWSA-N 0.000 claims 1
- 208000035143 Bacterial infection Diseases 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000001924 cycloalkanes Chemical class 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 238000002347 injection Methods 0.000 claims 1
- 239000007924 injection Substances 0.000 claims 1
- 238000001990 intravenous administration Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- JGKFRYAHUMFEPY-OAHLLOKOSA-N n-[(1r)-1-(3-ethyl-1-benzofuran-2-yl)ethyl]-n-methyl-3-(7-oxo-6,8-dihydro-5h-1,8-naphthyridin-3-yl)prop-2-enamide Chemical compound N1C(=O)CCC2=CC(C=CC(=O)N(C)[C@H](C)C3=C(C4=CC=CC=C4O3)CC)=CN=C21 JGKFRYAHUMFEPY-OAHLLOKOSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 230000001954 sterilising effect Effects 0.000 claims 1
- 238000007910 systemic administration Methods 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- 0 Cc1c(*)c(C(**)=C(*)C2)c2c(*)c1* Chemical compound Cc1c(*)c(C(**)=C(*)C2)c2c(*)c1* 0.000 description 3
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US74251405P | 2005-12-05 | 2005-12-05 | |
| US75402405P | 2005-12-23 | 2005-12-23 | |
| PCT/US2006/045903 WO2007067416A2 (en) | 2005-12-05 | 2006-12-01 | Heterocyclylacrylamide compounds as fabi inhibitors and antibacterial agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009518399A JP2009518399A (ja) | 2009-05-07 |
| JP2009518399A5 true JP2009518399A5 (cg-RX-API-DMAC7.html) | 2010-01-14 |
Family
ID=37945447
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008544384A Pending JP2009518399A (ja) | 2005-12-05 | 2006-12-01 | Ｆａｂｉ阻害剤および抗菌剤としてのヘテロ環アクリルアミド化合物 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20090156578A1 (cg-RX-API-DMAC7.html) |
| EP (1) | EP1973902A2 (cg-RX-API-DMAC7.html) |
| JP (1) | JP2009518399A (cg-RX-API-DMAC7.html) |
| KR (1) | KR20080075027A (cg-RX-API-DMAC7.html) |
| CA (1) | CA2632476A1 (cg-RX-API-DMAC7.html) |
| IL (1) | IL191987A0 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2007067416A2 (cg-RX-API-DMAC7.html) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU230030B1 (hu) | 1999-10-08 | 2015-05-28 | Debiopharm International Sa | Fab I inhibitorok |
| EP1560584B1 (en) * | 2001-04-06 | 2009-01-14 | Affinium Pharmaceuticals, Inc. | Fab i inhibitors |
| EP1575951B1 (en) * | 2002-12-06 | 2014-06-25 | Debiopharm International SA | Heterocyclic compounds, methods of making them and their use in therapy |
| DK1828167T3 (da) * | 2004-06-04 | 2014-10-20 | Debiopharm Int Sa | Acrylamidderivater som antibiotiske midler |
| JP5468899B2 (ja) | 2006-07-20 | 2014-04-09 | アフィニウム ファーマシューティカルズ， インク． | Ｆａｂｉインヒビターとしてのアクリルアミド誘導体 |
| EP2125802A4 (en) | 2007-02-16 | 2014-08-20 | Debiopharm Int Sa | SALTS, PRODRUGS AND POLYMORPHES OF FAB I INHIBITORS |
| JP5270943B2 (ja) * | 2008-03-28 | 2013-08-21 | 大阪瓦斯株式会社 | フルオレン誘導体およびこのフルオレン誘導体を用いたアミノ基含有フルオレン誘導体の製造方法 |
| MX2012001974A (es) | 2009-08-19 | 2012-04-11 | Ambit Biosciences Corp | Compuestos de biarilo y metodos de uso de los mismos. |
| WO2011061214A1 (en) * | 2009-11-18 | 2011-05-26 | Fab Pharma Sas | Novel heterocyclic acrylamides and their use as pharmaceuticals |
| CA2849057C (en) * | 2011-09-19 | 2021-05-11 | Vitas Pharma Research Pvt Ltd | Heterocyclic compounds as inhibitors of fatty acid biosynthesis for bacterial infections |
| AU2013279021C1 (en) | 2012-06-19 | 2017-03-16 | Debiopharm International Sa | Prodrug derivatives of (E)-N-methyl-N-((3-methylbenzofuran-2-yl)methyl)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide |
| IL287136B2 (en) | 2016-02-05 | 2023-09-01 | Denali Therapeutics Inc | Receptor inhibitors - interacting with protein kinase 1 |
| RS61312B1 (sr) | 2016-02-26 | 2021-02-26 | Debiopharm Int Sa | Lek za lečenje infekcija dijabetskog stopala |
| JP7208137B2 (ja) | 2016-12-09 | 2023-01-18 | デナリ セラピューティクス インコーポレイテッド | 化合物、組成物および方法 |
| US11691967B2 (en) | 2018-03-12 | 2023-07-04 | The Board Of Trustees Of The University Of Illinois | Antibiotics effective for gram-negative pathogens |
| SMT202400519T1 (it) * | 2018-11-12 | 2025-01-14 | Debiopharm Int Sa | Composti antibiotici. metodi di produzione degli stessi, composizioni farmaceutiche contenenti gli stessi e loro usi |
| TN2021000159A1 (en) | 2019-02-14 | 2023-04-04 | Debiopharm Int Sa | Afabicin formulation, method for making the same and uses thereof |
| SG11202113174SA (en) | 2019-06-14 | 2021-12-30 | Debiopharm Int Sa | Medicament and use thereof for treating bacterial infections involving biofilm |
| IL293980B1 (en) | 2019-12-19 | 2026-04-01 | Debiopharm Int Sa | New compounds and their use |
| WO2022187329A1 (en) * | 2021-03-03 | 2022-09-09 | The Board Of Trustees Of The University Of Illinois | Fabi inhibitors for gram-negative pathogens |
| US20240317740A1 (en) | 2021-06-23 | 2024-09-26 | Debiopharm International S.A. | Novel compounds and their use |
| CN113861137B (zh) * | 2021-09-26 | 2023-08-15 | 重庆医科大学 | 酮与alpha氯代酮一步反应合成呋喃类化合物的方法 |
| TW202334164A (zh) | 2022-01-12 | 2023-09-01 | 美商戴納立製藥公司 | （Ｓ）－５－苄基－Ｎ－（５－甲基－４－側氧基－２，３，４，５－四氫吡啶並［３，２－ｂ］［１，４］氧氮呯－３－基）－４Ｈ－１，２，４－三唑－３－甲醯胺的晶型 |
| CN121889392A (zh) * | 2023-10-07 | 2026-04-17 | 广州白云山医药集团股份有限公司白云山制药总厂 | 一种FabI酶抑制剂及其应用 |
| WO2025078209A1 (en) | 2023-10-09 | 2025-04-17 | Debiopharm International S.A. | Antibiotic compounds for treating bacterial infections |
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-
2006
- 2006-12-01 KR KR1020087016424A patent/KR20080075027A/ko not_active Ceased
- 2006-12-01 EP EP06844684A patent/EP1973902A2/en not_active Withdrawn
- 2006-12-01 US US12/095,977 patent/US20090156578A1/en not_active Abandoned
- 2006-12-01 JP JP2008544384A patent/JP2009518399A/ja active Pending
- 2006-12-01 WO PCT/US2006/045903 patent/WO2007067416A2/en not_active Ceased
- 2006-12-01 CA CA002632476A patent/CA2632476A1/en not_active Abandoned
-
2008
- 2008-06-05 IL IL191987A patent/IL191987A0/en unknown
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