JP2006511595A5 - - Google Patents
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- Publication number
- JP2006511595A5 JP2006511595A5 JP2005500077A JP2005500077A JP2006511595A5 JP 2006511595 A5 JP2006511595 A5 JP 2006511595A5 JP 2005500077 A JP2005500077 A JP 2005500077A JP 2005500077 A JP2005500077 A JP 2005500077A JP 2006511595 A5 JP2006511595 A5 JP 2006511595A5
- Authority
- JP
- Japan
- Prior art keywords
- quinoline
- pyrimidine
- oxazino
- tetrahydro
- trione
- 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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- YYFLDZZDOUDZQM-UHFFFAOYSA-N 3-[1-[[4-(3-phenylquinolin-2-yl)phenyl]methyl]piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound O=C1NC2=CC=CC=C2N1C(CC1)CCN1CC(C=C1)=CC=C1C1=NC2=CC=CC=C2C=C1C1=CC=CC=C1 YYFLDZZDOUDZQM-UHFFFAOYSA-N 0.000 description 42
- 125000000217 alkyl group Chemical group 0.000 description 37
- 125000005843 halogen group Chemical group 0.000 description 22
- 150000001875 compounds Chemical class 0.000 description 21
- 125000001072 heteroaryl group Chemical group 0.000 description 14
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
- 125000003003 spiro group Chemical group 0.000 description 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 125000004093 cyano group Chemical group *C#N 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- -1 piperazino Chemical group 0.000 description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 description 4
- 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 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 125000006413 ring segment Chemical group 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- DJZPHYIXNUOVJU-VYUIOLGVSA-N (2'r,4's,4'as)-2',4'-dimethyl-8'-nitrospiro[1,3-diazinane-5,5'-2,4,4a,6-tetrahydro-1h-[1,4]oxazino[4,3-a]quinoline]-2,4,6-trione Chemical compound C12([C@@H]3N(C4=CC=C(C=C4C1)[N+]([O-])=O)C[C@H](O[C@H]3C)C)C(=O)NC(=O)NC2=O DJZPHYIXNUOVJU-VYUIOLGVSA-N 0.000 description 2
- VWOKJEMOFYPRFI-KMUNFCNLSA-N (2's,4'r,4'ar)-4'-methyl-8'-nitro-2'-propan-2-ylspiro[1,3-diazinane-5,5'-2,4,4a,6-tetrahydro-1h-[1,4]oxazino[4,3-a]quinoline]-2,4,6-trione Chemical compound C12([C@H]3N(C4=CC=C(C=C4C1)[N+]([O-])=O)C[C@@H](O[C@@H]3C)C(C)C)C(=O)NC(=O)NC2=O VWOKJEMOFYPRFI-KMUNFCNLSA-N 0.000 description 2
- VOYADQIFGGIKAT-UHFFFAOYSA-N 1,3-dibutyl-4-hydroxy-2,6-dioxopyrimidine-5-carboximidamide Chemical compound CCCCn1c(O)c(C(N)=N)c(=O)n(CCCC)c1=O VOYADQIFGGIKAT-UHFFFAOYSA-N 0.000 description 2
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229910004013 NO 2 Inorganic materials 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 239000003880 polar aprotic solvent Substances 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- KTOXZBWKIGLPAO-BFHDXFOESA-N (2'r,4's,4'as)-10'-fluoro-2',4'-dimethyl-8'-nitrospiro[1,3-diazinane-5,5'-2,4,4a,6-tetrahydro-1h-[1,4]oxazino[4,3-a]quinoline]-2,4,6-trione Chemical compound C12([C@@H]3N(C4=C(F)C=C(C=C4C1)[N+]([O-])=O)C[C@H](O[C@H]3C)C)C(=O)NC(=O)NC2=O KTOXZBWKIGLPAO-BFHDXFOESA-N 0.000 description 1
- FPHJEBUPCOJKKB-VHDGCEQUSA-N (2'r,4's,4'as)-2',4'-diethyl-8'-nitrospiro[1,3-diazinane-5,5'-2,4,4a,6-tetrahydro-1h-[1,4]oxazino[4,3-a]quinoline]-2,4,6-trione Chemical compound C12([C@@H]3N(C4=CC=C(C=C4C1)[N+]([O-])=O)C[C@H](O[C@H]3CC)CC)C(=O)NC(=O)NC2=O FPHJEBUPCOJKKB-VHDGCEQUSA-N 0.000 description 1
- HNKUXJMVBMWIIM-HFBDOXOYSA-N (2'r,4's,4'as)-2',4'-dimethyl-8'-(3-methyl-1,2,4-oxadiazol-5-yl)spiro[1,3-diazinane-5,5'-2,4,4a,6-tetrahydro-1h-[1,4]oxazino[4,3-a]quinoline]-2,4,6-trione Chemical compound C12([C@@H]3N(C4=CC=C(C=C4C1)C=1ON=C(C)N=1)C[C@H](O[C@H]3C)C)C(=O)NC(=O)NC2=O HNKUXJMVBMWIIM-HFBDOXOYSA-N 0.000 description 1
- DWSKYPCBPFDJSI-HFBDOXOYSA-N (2'r,4's,4'as)-2',4'-dimethyl-8'-(5-methyl-1,2,4-oxadiazol-3-yl)spiro[1,3-diazinane-5,5'-2,4,4a,6-tetrahydro-1h-[1,4]oxazino[4,3-a]quinoline]-2,4,6-trione Chemical compound C12([C@@H]3N(C4=CC=C(C=C4C1)C=1N=C(C)ON=1)C[C@H](O[C@H]3C)C)C(=O)NC(=O)NC2=O DWSKYPCBPFDJSI-HFBDOXOYSA-N 0.000 description 1
- TXCGZVHSNIARKV-VYUIOLGVSA-N (2'r,4's,4'as)-2',4'-dimethyl-8'-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]spiro[1,3-diazinane-5,5'-2,4,4a,6-tetrahydro-1h-[1,4]oxazino[4,3-a]quinoline]-2,4,6-trione Chemical compound C12([C@@H]3N(C4=CC=C(C=C4C1)C=1N=C(ON=1)C(F)(F)F)C[C@H](O[C@H]3C)C)C(=O)NC(=O)NC2=O TXCGZVHSNIARKV-VYUIOLGVSA-N 0.000 description 1
- DPWWEZBVUHNFPA-YESZJQIVSA-N (2'r,4's,4'as)-8'-nitro-2',4'-di(propan-2-yl)spiro[1,3-diazinane-5,5'-2,4,4a,6-tetrahydro-1h-[1,4]oxazino[4,3-a]quinoline]-2,4,6-trione Chemical compound C12([C@@H]3N(C4=CC=C(C=C4C1)[N+]([O-])=O)C[C@H](O[C@H]3C(C)C)C(C)C)C(=O)NC(=O)NC2=O DPWWEZBVUHNFPA-YESZJQIVSA-N 0.000 description 1
- BVZNGKUUIYZYIC-VQISRLSMSA-N (2's,4'r,4'ar)-2'-methyl-8'-nitro-4'-propan-2-ylspiro[1,3-diazinane-5,5'-2,4,4a,6-tetrahydro-1h-[1,4]oxazino[4,3-a]quinoline]-2,4,6-trione Chemical compound C12([C@H]3N(C4=CC=C(C=C4C1)[N+]([O-])=O)C[C@H](C)O[C@@H]3C(C)C)C(=O)NC(=O)NC2=O BVZNGKUUIYZYIC-VQISRLSMSA-N 0.000 description 1
- GOZJOFUKPXUVGK-FLBPPNCPSA-N (2's,4'r,4'ar)-8'-acetyl-10'-fluoro-2',4'-dimethylspiro[1,3-diazinane-5,5'-2,4,4a,6-tetrahydro-1h-[1,4]oxazino[4,3-a]quinoline]-2,4,6-trione Chemical compound C12([C@H]3N(C4=C(F)C=C(C=C4C1)C(C)=O)C[C@@H](O[C@@H]3C)C)C(=O)NC(=O)NC2=O GOZJOFUKPXUVGK-FLBPPNCPSA-N 0.000 description 1
- DJZPHYIXNUOVJU-MWODSPESSA-N (2's,4's,4'as)-2',4'-dimethyl-8'-nitrospiro[1,3-diazinane-5,5'-2,4,4a,6-tetrahydro-1h-[1,4]oxazino[4,3-a]quinoline]-2,4,6-trione Chemical compound C12([C@@H]3N(C4=CC=C(C=C4C1)[N+]([O-])=O)C[C@@H](O[C@H]3C)C)C(=O)NC(=O)NC2=O DJZPHYIXNUOVJU-MWODSPESSA-N 0.000 description 1
- IYEUXQBYWAQYBT-MTJIALIYSA-N (4-azido-3-iodophenyl)methyl (2'r,4's,4'as)-2',4'-dimethyl-2,4,6-trioxospiro[1,3-diazinane-5,5'-2,4,4a,6-tetrahydro-1h-[1,4]oxazino[4,3-a]quinoline]-8'-carboxylate Chemical compound C12([C@@H]3N(C4=CC=C(C=C4C1)C(=O)OCC=1C=C(I)C(N=[N+]=[N-])=CC=1)C[C@H](O[C@H]3C)C)C(=O)NC(=O)NC2=O IYEUXQBYWAQYBT-MTJIALIYSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- WCFAPJDPAPDDAQ-UHFFFAOYSA-N 1,2-dihydropyrimidine Chemical compound C1NC=CC=N1 WCFAPJDPAPDDAQ-UHFFFAOYSA-N 0.000 description 1
- NELXOBPOTDGLGF-UHFFFAOYSA-N 1,3,3'-trimethylspiro[1,3-diazinane-5,5'-2,4,4a,6-tetrahydro-1h-pyrazino[1,2-a]quinoline]-2,4,6-trione Chemical compound C1N(C)CCN(C2=CC=CC=C2C2)C1C12C(=O)N(C)C(=O)N(C)C1=O NELXOBPOTDGLGF-UHFFFAOYSA-N 0.000 description 1
- QPBCJPQUTNKKRC-UHFFFAOYSA-N 2,4-dimethyl-2,4,4a,6-tetrahydro-1h-[1,4]oxazino[4,3-a]quinoline-5,5,8-tricarbonitrile Chemical compound N#CC1=CC=C2N3CC(C)OC(C)C3C(C#N)(C#N)CC2=C1 QPBCJPQUTNKKRC-UHFFFAOYSA-N 0.000 description 1
- YTAFQYJFWFUTBT-UHFFFAOYSA-N 8'-bromo-2',4'-dimethyl-10'-nitrospiro[1,3-diazinane-5,5'-2,4,4a,6-tetrahydro-1h-[1,4]oxazino[4,3-a]quinoline]-2,4,6-trione Chemical compound CC1OC(C)CN(C2=C(C=C(Br)C=C2C2)[N+]([O-])=O)C1C12C(=O)NC(=O)NC1=O YTAFQYJFWFUTBT-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 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
- 125000002527 bicyclic carbocyclic group Chemical group 0.000 description 1
- 125000002618 bicyclic heterocycle group Chemical group 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical compound O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 description 1
- LOGSONSNCYTHPS-UHFFFAOYSA-N cyclopentane-1,3-dione Chemical compound O=C1CCC(=O)C1 LOGSONSNCYTHPS-UHFFFAOYSA-N 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- AOGRSAIQGKKYQV-UHFFFAOYSA-N spiro[1,3-diazinane-5,5'-6h-[1,4]oxazino[4,3-a]quinoline]-2,4,6-trione Chemical compound O=C1NC(=O)NC(=O)C11C2=COC=CN2C2=CC=CC=C2C1 AOGRSAIQGKKYQV-UHFFFAOYSA-N 0.000 description 1
- XRRIMVJNMINTBJ-UHFFFAOYSA-N spiro[1,3-diazinane-5,5'-6h-[1,4]thiazino[4,3-a]quinoline]-2,4,6-trione Chemical compound O=C1NC(=O)NC(=O)C11C2=CSC=CN2C2=CC=CC=C2C1 XRRIMVJNMINTBJ-UHFFFAOYSA-N 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000010512 thermal transition Effects 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41668502P | 2002-10-07 | 2002-10-07 | |
| US42718902P | 2002-11-18 | 2002-11-18 | |
| US45762203P | 2003-03-26 | 2003-03-26 | |
| PCT/IB2003/004389 WO2004031195A1 (en) | 2002-10-07 | 2003-10-03 | Tricyclic tetrahydroquinoline antibacterial agents |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2006511595A JP2006511595A (ja) | 2006-04-06 |
| JP2006511595A5 true JP2006511595A5 (enExample) | 2006-11-24 |
| JP4009652B2 JP4009652B2 (ja) | 2007-11-21 |
Family
ID=32074379
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2005500077A Expired - Fee Related JP4009652B2 (ja) | 2002-10-07 | 2003-10-03 | 三環式テトラヒドロキノリン抗細菌剤 |
Country Status (16)
| Country | Link |
|---|---|
| US (4) | US7208490B2 (enExample) |
| EP (1) | EP1551849B1 (enExample) |
| JP (1) | JP4009652B2 (enExample) |
| AR (1) | AR041546A1 (enExample) |
| AT (1) | ATE473985T1 (enExample) |
| AU (1) | AU2003264768A1 (enExample) |
| BR (1) | BR0315139A (enExample) |
| CA (1) | CA2500824C (enExample) |
| CY (1) | CY1110821T1 (enExample) |
| DE (1) | DE60333379D1 (enExample) |
| DK (1) | DK1551849T3 (enExample) |
| MX (1) | MXPA05002701A (enExample) |
| PT (1) | PT1551849E (enExample) |
| SI (1) | SI1551849T1 (enExample) |
| TW (1) | TWI295671B (enExample) |
| WO (1) | WO2004031195A1 (enExample) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7208490B2 (en) | 2002-10-07 | 2007-04-24 | Pharmacia & Upjohn Company Llc | Tricyclic tetrahydroquinoline antibacterial agents |
| JP2008543739A (ja) * | 2005-05-09 | 2008-12-04 | ワーナー−ランバート カンパニー リミテッド ライアビリティー カンパニー | 抗菌剤 |
| DOP2006000268A (es) * | 2005-12-22 | 2007-07-31 | Pfizer Prod Inc | Agentes antibacterianos |
| CN101784553A (zh) * | 2007-07-02 | 2010-07-21 | 阿斯利康(瑞典)有限公司 | 3-螺嘧啶三酮-喹啉衍生物及其作为抗菌药物的应用 |
| RU2010105007A (ru) | 2007-07-16 | 2011-08-27 | Астразенека Аб (Se) | Химические соединения |
| AU2009305203B2 (en) * | 2008-10-14 | 2013-03-07 | Entasis Therapeutics Limited | Fused, spirocyclic heteroaromatic compounds for the treatment of bacterial infections |
| US9040528B2 (en) | 2008-10-14 | 2015-05-26 | Astrazeneca Ab | Chemical compounds 542 |
| WO2010075380A1 (en) * | 2008-12-23 | 2010-07-01 | Abbott Laboratories | Anti-viral compounds |
| BR112013001138A2 (pt) | 2010-07-16 | 2016-07-05 | Abbvie Inc | ligantes de fosfina para reações catalíticas |
| US8975443B2 (en) | 2010-07-16 | 2015-03-10 | Abbvie Inc. | Phosphine ligands for catalytic reactions |
| WO2012009699A2 (en) | 2010-07-16 | 2012-01-19 | Abbott Laboratories | Process for preparing antiviral compounds |
| US9255074B2 (en) | 2010-07-16 | 2016-02-09 | Abbvie Inc. | Process for preparing antiviral compounds |
| RU2644250C2 (ru) * | 2012-09-14 | 2018-02-08 | Элизабет ЛЕВИНА | Лекарственное средство с активностью против грамположительных бактерий, микобактерий и грибов |
| US8952149B2 (en) | 2012-09-26 | 2015-02-10 | Zoetis Llc | Tricyclic tetrahydroquinoline antibacterial agents |
| US8889671B2 (en) | 2013-01-23 | 2014-11-18 | Astrazeneca Ab | Compounds and methods for treating bacterial infections |
| JP6156845B2 (ja) * | 2014-03-04 | 2017-07-05 | 株式会社島津製作所 | マトリックス支援レーザ脱離イオン化質量分析用マトリックス |
| EA033459B1 (ru) | 2014-05-29 | 2019-10-31 | Entasis Therapeutics Ltd | Конденсированные спироциклические гетероароматические соединения для лечения бактериальных инфекций |
| WO2017156519A1 (en) | 2016-03-11 | 2017-09-14 | The Board Of Trustees Of The University Of Illinois | Small-molecules active against gram-negative bacteria |
| US11274106B2 (en) | 2017-06-23 | 2022-03-15 | The Board Of Trustees Of The University Of Illinois | Topoisomerase inhibitors with antibacterial and anticancer activity |
| CN108101860B (zh) * | 2018-02-08 | 2021-11-23 | 苏州敬业医药化工有限公司 | 顺式-2，6-二甲基吗啉的制备方法 |
| CN115466212B (zh) * | 2022-10-26 | 2023-09-22 | 河南农业大学 | 一种2-三氟甲基喹啉类化合物及其合成方法和应用 |
| CN118878546B (zh) * | 2024-09-30 | 2025-01-03 | 苏州大学 | 一种螺环巴比妥酸衍生物及其制备方法和应用 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5011860A (en) | 1986-04-11 | 1991-04-30 | Schering Corporation | Aryl-substituted naphthyridine and pyridopyrazine derivatives and their use in treating hyperproliferative skin diseases |
| DE19502178A1 (de) | 1994-01-27 | 1995-08-03 | Hoechst Ag | Thiadiazolderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Vorprodukte zur Herstellung von Flüssigkristallen |
| CA2425283A1 (en) | 2000-10-26 | 2002-05-02 | Pfizer Products Inc. | Spiro-pyrimidine-2,4,6-trione metalloproteinase inhibitors |
| WO2003091252A1 (en) | 2002-04-25 | 2003-11-06 | Bristol-Myers Squibb Company | Spirobarbituric acid derivatives useful as inhibitors of matrix metalloproteases |
| US7208490B2 (en) | 2002-10-07 | 2007-04-24 | Pharmacia & Upjohn Company Llc | Tricyclic tetrahydroquinoline antibacterial agents |
| MXPA05003774A (es) | 2002-10-10 | 2005-06-08 | Pharmacia & Upjohn Co Llc | Compuestos de 1-aril-dihidropiridona con actividad antimicrobiana. |
-
2003
- 2003-10-02 US US10/677,551 patent/US7208490B2/en not_active Expired - Fee Related
- 2003-10-03 MX MXPA05002701A patent/MXPA05002701A/es active IP Right Grant
- 2003-10-03 CA CA2500824A patent/CA2500824C/en not_active Expired - Fee Related
- 2003-10-03 DE DE60333379T patent/DE60333379D1/de not_active Expired - Lifetime
- 2003-10-03 PT PT03799056T patent/PT1551849E/pt unknown
- 2003-10-03 DK DK03799056.1T patent/DK1551849T3/da active
- 2003-10-03 BR BR0315139-5A patent/BR0315139A/pt not_active IP Right Cessation
- 2003-10-03 WO PCT/IB2003/004389 patent/WO2004031195A1/en not_active Ceased
- 2003-10-03 JP JP2005500077A patent/JP4009652B2/ja not_active Expired - Fee Related
- 2003-10-03 AT AT03799056T patent/ATE473985T1/de active
- 2003-10-03 AU AU2003264768A patent/AU2003264768A1/en not_active Abandoned
- 2003-10-03 EP EP03799056A patent/EP1551849B1/en not_active Expired - Lifetime
- 2003-10-03 SI SI200331869T patent/SI1551849T1/sl unknown
- 2003-10-06 TW TW092127679A patent/TWI295671B/zh not_active IP Right Cessation
- 2003-10-07 AR ARP030103650A patent/AR041546A1/es not_active Application Discontinuation
-
2007
- 2007-03-07 US US11/715,213 patent/US7605157B2/en not_active Expired - Fee Related
-
2009
- 2009-08-28 US US12/549,407 patent/US20100022524A1/en not_active Abandoned
-
2010
- 2010-10-06 CY CY20101100894T patent/CY1110821T1/el unknown
- 2010-12-20 US US12/972,921 patent/US8420646B2/en not_active Expired - Fee Related
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