JP2008513485A - キノロンアナログ - Google Patents
キノロンアナログ Download PDFInfo
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- JP2008513485A JP2008513485A JP2007532545A JP2007532545A JP2008513485A JP 2008513485 A JP2008513485 A JP 2008513485A JP 2007532545 A JP2007532545 A JP 2007532545A JP 2007532545 A JP2007532545 A JP 2007532545A JP 2008513485 A JP2008513485 A JP 2008513485A
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- 150000007660 quinolones Chemical class 0.000 title abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 133
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 211
- 239000000203 mixture Substances 0.000 claims description 153
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- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 43
- 125000000217 alkyl group Chemical group 0.000 claims description 42
- 125000000623 heterocyclic group Chemical group 0.000 claims description 38
- 238000011282 treatment Methods 0.000 claims description 35
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical class C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 33
- 125000001072 heteroaryl group Chemical group 0.000 claims description 32
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- 206010028980 Neoplasm Diseases 0.000 claims description 30
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- 125000003118 aryl group Chemical group 0.000 claims description 26
- 125000005842 heteroatom Chemical group 0.000 claims description 26
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 24
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- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 22
- 125000005843 halogen group Chemical group 0.000 claims description 21
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- 239000008194 pharmaceutical composition Substances 0.000 claims description 12
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- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical class C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 9
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- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 8
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
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- 125000003545 alkoxy group Chemical group 0.000 claims description 6
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
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- 125000004122 cyclic group Chemical group 0.000 claims description 5
- SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 claims description 5
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- 230000003612 virological effect Effects 0.000 claims description 5
- NIWIKUAWVYZYBD-UHFFFAOYSA-N 3h-dithiazol-4-amine Chemical compound NC1=CSSN1 NIWIKUAWVYZYBD-UHFFFAOYSA-N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
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- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
- 150000001540 azides Chemical class 0.000 claims description 3
- 238000004440 column chromatography Methods 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
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- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 2
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- 229910052787 antimony Inorganic materials 0.000 claims description 2
- 229910052785 arsenic Inorganic materials 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 229910021480 group 4 element Inorganic materials 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 238000001356 surgical procedure Methods 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- JJSKFMMFEZVDRS-UHFFFAOYSA-N N1C=CC=C1.NP1SSP1 Chemical class N1C=CC=C1.NP1SSP1 JJSKFMMFEZVDRS-UHFFFAOYSA-N 0.000 claims 1
- 230000001771 impaired effect Effects 0.000 claims 1
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- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 1
- 230000005855 radiation Effects 0.000 claims 1
- 238000012360 testing method Methods 0.000 description 207
- 239000000243 solution Substances 0.000 description 170
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 144
- 239000007787 solid Substances 0.000 description 131
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 124
- 210000004027 cell Anatomy 0.000 description 120
- 238000006243 chemical reaction Methods 0.000 description 102
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 93
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 86
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 76
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 74
- 238000003556 assay Methods 0.000 description 73
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 66
- 239000002904 solvent Substances 0.000 description 63
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 58
- 239000000047 product Substances 0.000 description 58
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- 150000007523 nucleic acids Chemical class 0.000 description 57
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 56
- 108020004414 DNA Proteins 0.000 description 55
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 27
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 26
- 239000012267 brine Substances 0.000 description 26
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- 235000011152 sodium sulphate Nutrition 0.000 description 26
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 26
- 238000001990 intravenous administration Methods 0.000 description 25
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
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- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 14
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Classifications
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- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
- C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains three hetero rings
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| PCT/US2005/033323 WO2006034113A2 (en) | 2004-09-17 | 2005-09-16 | Quinolone analogs as cell proliferation inhibitors |
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| JP2018537486A (ja) * | 2015-12-14 | 2018-12-20 | センワ バイオサイエンシズ インコーポレイテッド | キノロン類似体及びその塩の結晶形 |
| JP2020189888A (ja) * | 2020-08-28 | 2020-11-26 | センワ バイオサイエンシズ インコーポレイテッド | キノロン類似体及びその塩の結晶形 |
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| PT1928887E (pt) | 2005-08-05 | 2015-02-12 | Senhwa Biosciences Inc | Métodos de preparação de análogos de quinolona |
| US20110112086A1 (en) * | 2006-06-08 | 2011-05-12 | Cylene Pharmaceuticals, Inc. | Pyridinone analogs |
| US20100305136A1 (en) * | 2006-06-08 | 2010-12-02 | Johnny Yasuo Nagasawa | Quinolone analogs derivatized with sulfonic acid, sulfonate or sulfonamide |
| BRPI0719123A2 (pt) | 2006-09-01 | 2013-12-17 | Cylene Pharmaceuticals Inc | Moduladores de serina-treonina proteína cinase e parp |
| US20080318938A1 (en) * | 2007-06-22 | 2008-12-25 | Ryckman David M | Methods for treating aberrant cell proliferation disorders |
| WO2009002838A1 (en) * | 2007-06-22 | 2008-12-31 | Cylene Pharmaceuticals, Inc. | Methods for treating ophthalmic disorders |
| WO2009097014A2 (en) * | 2007-08-31 | 2009-08-06 | Cylene Pharmaceuticals, Inc. | Therapeutic kinase modulators |
| JP5461405B2 (ja) | 2007-09-14 | 2014-04-02 | バーテックス ファーマシューティカルズ インコーポレイテッド | 嚢胞性線維症膜コンダクタンス制御因子の調節因子 |
| PT3092901T (pt) | 2007-10-05 | 2020-05-21 | Senhwa Biosciences Inc | Análogos de quinolona e respetivos métodos relacionados |
| WO2011031745A1 (en) | 2009-09-09 | 2011-03-17 | Achaogen, Inc. | Antibacterial fluoroquinolone analogs |
| RU2435758C1 (ru) * | 2010-07-19 | 2011-12-10 | Государственное образовательное учреждение высшего профессионального образования Волгоградский государственный технический университет (ВолгГТУ) | Способ получения этилового эфира 3-оксо-3-(2,6-дихлорпиридин-3-ил) пропановой кислоты |
| CA2948173C (en) | 2014-05-09 | 2018-06-19 | Pimera, Inc. | Quinoline compounds and uses thereof |
| US9758518B2 (en) | 2015-03-04 | 2017-09-12 | Pimera, Inc. | Compositions, uses and methods for making them |
| WO2016137471A1 (en) * | 2015-02-26 | 2016-09-01 | Nantpharma, Llc | Method for enhanced heparin quality |
| CN119185322A (zh) | 2015-11-20 | 2024-12-27 | 生华生物科技股份有限公司 | 用于治疗癌症的四环喹诺酮类似物组合疗法 |
| US9957282B2 (en) | 2015-12-14 | 2018-05-01 | Senhwa Biosciences, Inc. | Crystalline forms of quinolone analogs and their salts |
| CN110709400A (zh) | 2017-03-28 | 2020-01-17 | 皮梅拉股份有限公司 | Pol1抑制剂的新型晶体形式 |
| RU2020130050A (ru) | 2018-02-15 | 2022-03-15 | Сэньхва Байосайенсиз, Инк. | Аналоги хинолонов и их соли, композиции и способ их применения |
| WO2025114459A1 (en) * | 2023-11-28 | 2025-06-05 | Genome Therapeutics Ltd | Tetracyclic compounds for use in antibody-drug conjugates for the treatment of cancer |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JPS54132582A (en) * | 1978-02-24 | 1979-10-15 | Bayer Ag | Manufacture of 44pyridonee33carboxylic acid and*or its derivative |
| US4959363A (en) * | 1989-06-23 | 1990-09-25 | Sterling Drug Inc. | Quinolonecarboxamide compounds, their preparation and use as antivirals. |
| JPH04117388A (ja) * | 1990-09-07 | 1992-04-17 | Hokuriku Seiyaku Co Ltd | チアゾロキノリン―4―カルボン酸誘導体 |
| JPH07252228A (ja) * | 1994-02-07 | 1995-10-03 | Fujisawa Pharmaceut Co Ltd | キノリン誘導体 |
| US20020025960A1 (en) * | 2000-07-12 | 2002-02-28 | Bundy Gordon L. | Heterocycle carboxamides as antiviral agents |
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| DE3267485D1 (en) * | 1981-02-18 | 1986-01-02 | Nippon Shinyaku Co Ltd | Substituted carboxylic acid derivatives |
| ZA852769B (en) * | 1984-04-26 | 1985-11-27 | Abbott Lab | Benzothiazolo-quinoline antibacterial compounds |
| ZA852802B (en) * | 1984-04-26 | 1985-11-27 | Abbott Lab | Benzoxazolo-quinoline antibacterial compounds |
| US4528285A (en) * | 1984-04-26 | 1985-07-09 | Abbott Laboratories | Methylenedioxy quino-benzothiazine derivatives |
| WO1989012055A1 (fr) * | 1988-06-08 | 1989-12-14 | Kyorin Pharmaceutical Co., Ltd. | Agent antitumoral |
| IE912902A1 (en) | 1990-08-24 | 1992-02-26 | Abbott Lab | Quinbenzoxazine, quinobenzothiazine, and pyrido-acridine¹antineoplastic agents |
| US5646163A (en) * | 1992-10-30 | 1997-07-08 | The Procter & Gamble Company | Quinolone 5-(N-heterosubstituted amino) antimicrobials |
| US6699989B1 (en) * | 2000-08-28 | 2004-03-02 | B. Vithal Shetty | Antiviral and antimicrobial guanidine or biguanidine derivatives |
| HUP0303410A3 (en) | 2000-12-14 | 2005-12-28 | Procter & Gamble | Antimicrobial quinolones, pharmaceutical compositions containing them and their use |
| US6821969B2 (en) * | 2001-02-13 | 2004-11-23 | Pharmacia & Upjohn Company | Thioxazinoquinolones as antiviral agents |
| US6900224B2 (en) | 2002-07-31 | 2005-05-31 | The Procter & Gamble Company | Antimicrobial quinolones, their compositions and uses |
| NZ543006A (en) * | 2003-04-07 | 2009-03-31 | Cylene Pharmaceuticals Inc | Substituted quinobenzoxazine analogs |
| JP5317472B2 (ja) | 2004-03-15 | 2013-10-16 | サネシス ファーマシューティカルズ, インコーポレイテッド | Sns−595、及びその使用方法 |
-
2005
- 2005-09-16 MX MX2007003282A patent/MX2007003282A/es not_active Application Discontinuation
- 2005-09-16 BR BRPI0515319-0A patent/BRPI0515319A/pt not_active IP Right Cessation
- 2005-09-16 JP JP2007532545A patent/JP2008513485A/ja not_active Ceased
- 2005-09-16 KR KR1020077008765A patent/KR100989029B1/ko not_active Expired - Fee Related
- 2005-09-16 NZ NZ553746A patent/NZ553746A/en not_active IP Right Cessation
- 2005-09-16 WO PCT/US2005/033323 patent/WO2006034113A2/en not_active Ceased
- 2005-09-16 EP EP05813754A patent/EP1802306A2/en not_active Withdrawn
- 2005-09-16 CA CA2580749A patent/CA2580749C/en not_active Expired - Lifetime
- 2005-09-16 US US11/228,636 patent/US7816406B2/en active Active
- 2005-09-16 AU AU2005286965A patent/AU2005286965B2/en not_active Expired
-
2007
- 2007-03-12 IL IL181857A patent/IL181857A0/en unknown
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54132582A (en) * | 1978-02-24 | 1979-10-15 | Bayer Ag | Manufacture of 44pyridonee33carboxylic acid and*or its derivative |
| US4959363A (en) * | 1989-06-23 | 1990-09-25 | Sterling Drug Inc. | Quinolonecarboxamide compounds, their preparation and use as antivirals. |
| JPH04117388A (ja) * | 1990-09-07 | 1992-04-17 | Hokuriku Seiyaku Co Ltd | チアゾロキノリン―4―カルボン酸誘導体 |
| JPH07252228A (ja) * | 1994-02-07 | 1995-10-03 | Fujisawa Pharmaceut Co Ltd | キノリン誘導体 |
| US20020025960A1 (en) * | 2000-07-12 | 2002-02-28 | Bundy Gordon L. | Heterocycle carboxamides as antiviral agents |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2018537486A (ja) * | 2015-12-14 | 2018-12-20 | センワ バイオサイエンシズ インコーポレイテッド | キノロン類似体及びその塩の結晶形 |
| JP2020189888A (ja) * | 2020-08-28 | 2020-11-26 | センワ バイオサイエンシズ インコーポレイテッド | キノロン類似体及びその塩の結晶形 |
| JP2022179783A (ja) * | 2020-08-28 | 2022-12-02 | センワ バイオサイエンシズ インコーポレイテッド | キノロン類似体及びその塩の結晶形 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2006034113A3 (en) | 2006-08-24 |
| KR20070085264A (ko) | 2007-08-27 |
| WO2006034113A2 (en) | 2006-03-30 |
| EP1802306A2 (en) | 2007-07-04 |
| MX2007003282A (es) | 2007-10-16 |
| CA2580749C (en) | 2014-01-28 |
| KR100989029B1 (ko) | 2010-10-25 |
| NZ553746A (en) | 2010-06-25 |
| US20060074089A1 (en) | 2006-04-06 |
| AU2005286965B2 (en) | 2009-10-22 |
| IL181857A0 (en) | 2007-07-04 |
| US7816406B2 (en) | 2010-10-19 |
| AU2005286965A1 (en) | 2006-03-30 |
| BRPI0515319A (pt) | 2008-07-22 |
| CA2580749A1 (en) | 2006-03-30 |
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