JP2010517983A5 - - Google Patents
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- JP2010517983A5 JP2010517983A5 JP2009547728A JP2009547728A JP2010517983A5 JP 2010517983 A5 JP2010517983 A5 JP 2010517983A5 JP 2009547728 A JP2009547728 A JP 2009547728A JP 2009547728 A JP2009547728 A JP 2009547728A JP 2010517983 A5 JP2010517983 A5 JP 2010517983A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- hydrogen atom
- compound
- carbon atoms
- formula
- 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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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 61
- 150000001875 compounds Chemical class 0.000 claims 60
- 125000004432 carbon atom Chemical group C* 0.000 claims 41
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 22
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 21
- 125000000217 alkyl group Chemical group 0.000 claims 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 17
- 125000003545 alkoxy group Chemical group 0.000 claims 15
- 239000008194 pharmaceutical composition Substances 0.000 claims 15
- 229910052801 chlorine Inorganic materials 0.000 claims 14
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 13
- 239000004480 active ingredient Substances 0.000 claims 13
- 239000000460 chlorine Substances 0.000 claims 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 12
- 229910052794 bromium Inorganic materials 0.000 claims 12
- 229910052731 fluorine Inorganic materials 0.000 claims 10
- 125000005843 halogen group Chemical group 0.000 claims 10
- 229910052740 iodine Inorganic materials 0.000 claims 10
- 125000003277 amino group Chemical group 0.000 claims 9
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 9
- 239000000203 mixture Substances 0.000 claims 9
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 5
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims 5
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 5
- 235000019253 formic acid Nutrition 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 5
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 4
- 208000035143 Bacterial infection Diseases 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 4
- 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 4
- 230000003287 optical effect Effects 0.000 claims 4
- -1 N, N-dimethylamino group Chemical group 0.000 claims 3
- 208000022362 bacterial infectious disease Diseases 0.000 claims 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 3
- 230000003902 lesion Effects 0.000 claims 3
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 claims 2
- GSDSWSVVBLHKDQ-UHFFFAOYSA-N 9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid Chemical compound FC1=CC(C(C(C(O)=O)=C2)=O)=C3N2C(C)COC3=C1N1CCN(C)CC1 GSDSWSVVBLHKDQ-UHFFFAOYSA-N 0.000 claims 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 125000004849 alkoxymethyl group Chemical group 0.000 claims 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 229960003405 ciprofloxacin Drugs 0.000 claims 2
- 229960002549 enoxacin Drugs 0.000 claims 2
- IDYZIJYBMGIQMJ-UHFFFAOYSA-N enoxacin Chemical compound N1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1 IDYZIJYBMGIQMJ-UHFFFAOYSA-N 0.000 claims 2
- 229940124307 fluoroquinolone Drugs 0.000 claims 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
- 229960003376 levofloxacin Drugs 0.000 claims 2
- 229960003702 moxifloxacin Drugs 0.000 claims 2
- 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 2
- 229960001180 norfloxacin Drugs 0.000 claims 2
- OGJPXUAPXNRGGI-UHFFFAOYSA-N norfloxacin Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1 OGJPXUAPXNRGGI-UHFFFAOYSA-N 0.000 claims 2
- 229960001699 ofloxacin Drugs 0.000 claims 2
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims 2
- 229960004236 pefloxacin Drugs 0.000 claims 2
- FHFYDNQZQSQIAI-UHFFFAOYSA-N pefloxacin Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCN(C)CC1 FHFYDNQZQSQIAI-UHFFFAOYSA-N 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- SYNHCENRCUAUNM-UHFFFAOYSA-N Nitrogen mustard N-oxide hydrochloride Chemical class Cl.ClCC[N+]([O-])(C)CCCl SYNHCENRCUAUNM-UHFFFAOYSA-N 0.000 claims 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims 1
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- 239000003242 anti bacterial agent Substances 0.000 claims 1
- 230000000844 anti-bacterial effect Effects 0.000 claims 1
- 239000004599 antimicrobial Substances 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical group 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 230000007774 longterm Effects 0.000 claims 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 150000002923 oximes Chemical class 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 0 C[C@@]1*CCCC1 Chemical compound C[C@@]1*CCCC1 0.000 description 7
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0700717 | 2007-02-01 | ||
| FR0700717A FR2912133B1 (fr) | 2007-02-01 | 2007-02-01 | Nouveaux derives indoliques,leurs procedes de preparation et leurs utilisations notamment en tant qu'antibacteriens |
| PCT/FR2008/000118 WO2008110690A2 (fr) | 2007-02-01 | 2008-01-31 | Nouveaux derives indoliques, leurs procedes de preparation et leurs utilisations notamment en tant qu'antibacteriens |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010517983A JP2010517983A (ja) | 2010-05-27 |
| JP2010517983A5 true JP2010517983A5 (cg-RX-API-DMAC7.html) | 2010-12-02 |
| JP5368317B2 JP5368317B2 (ja) | 2013-12-18 |
Family
ID=38476052
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009547728A Expired - Fee Related JP5368317B2 (ja) | 2007-02-01 | 2008-01-31 | 新規なインドール誘導体それらの製造方法および特に抗菌剤としてのそれらの使用 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8343964B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP2121601B8 (cg-RX-API-DMAC7.html) |
| JP (1) | JP5368317B2 (cg-RX-API-DMAC7.html) |
| CN (1) | CN101652346B (cg-RX-API-DMAC7.html) |
| AU (1) | AU2008224776B2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2677146C (cg-RX-API-DMAC7.html) |
| FR (1) | FR2912133B1 (cg-RX-API-DMAC7.html) |
| RU (1) | RU2464261C2 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2008110690A2 (cg-RX-API-DMAC7.html) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011060976A1 (en) | 2009-11-20 | 2011-05-26 | Universite De Liege | Tryptamine-derived compounds as antibacterial agents |
| 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 |
| ES2464598T3 (es) | 2011-07-22 | 2014-06-03 | Université Joseph Fourier | Nuevos derivados bis-indólicos, procedimiento para su preparación, y sus utilizaciones como fármaco |
| ES2461997T3 (es) | 2011-07-22 | 2014-05-22 | Université Joseph Fourier | Derivados bis-indólicos nuevos, sus usos, en particular como antibacterianos |
| EP2639220A1 (en) * | 2012-03-15 | 2013-09-18 | Omnia Molecular, S. L. | Indole derivatives and their use as antibiotics |
| CN103664733B (zh) * | 2013-12-10 | 2016-04-20 | 邯郸惠达化工有限公司 | 一种吲哚啉的制备方法 |
| CN105669519B (zh) * | 2016-01-04 | 2018-01-05 | 北方民族大学 | 吲哚类化合物、制备方法及其作为抗耐药菌药物的应用 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4492694A (en) * | 1983-04-12 | 1985-01-08 | Eli Lilly And Company | Indolylglycyl cephalosporin derivatives |
| US5328902A (en) * | 1992-08-13 | 1994-07-12 | American Cyanamid Co. | 7-(substituted)-9-[(substituted glycyl)amido]-6-demethyl-6-deoxytetracyclines |
| AU2002367773A1 (en) * | 2001-04-06 | 2003-11-03 | Affinium Pharmaceuticals, Inc. | Fab i inhibitors |
| JP4880448B2 (ja) | 2003-03-17 | 2012-02-22 | アフィナム ファーマシューティカルズ，インコーポレーテッド | 複数の抗生物質を含む組成物、及びそれを用いる方法 |
| DE10320453A1 (de) * | 2003-05-08 | 2004-11-25 | Morphochem AG Aktiengesellschaft für kombinatorische Chemie | Neue Bioisostere von Actinonin |
-
2007
- 2007-02-01 FR FR0700717A patent/FR2912133B1/fr not_active Expired - Fee Related
-
2008
- 2008-01-31 US US12/525,503 patent/US8343964B2/en not_active Expired - Fee Related
- 2008-01-31 CA CA2677146A patent/CA2677146C/fr not_active Expired - Fee Related
- 2008-01-31 RU RU2009132657/04A patent/RU2464261C2/ru not_active IP Right Cessation
- 2008-01-31 JP JP2009547728A patent/JP5368317B2/ja not_active Expired - Fee Related
- 2008-01-31 CN CN2008800097669A patent/CN101652346B/zh not_active Expired - Fee Related
- 2008-01-31 WO PCT/FR2008/000118 patent/WO2008110690A2/fr not_active Ceased
- 2008-01-31 EP EP08761826.0A patent/EP2121601B8/fr not_active Not-in-force
- 2008-01-31 AU AU2008224776A patent/AU2008224776B2/en not_active Ceased
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