JP2010536713A5 - - Google Patents
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- Publication number
- JP2010536713A5 JP2010536713A5 JP2010506468A JP2010506468A JP2010536713A5 JP 2010536713 A5 JP2010536713 A5 JP 2010536713A5 JP 2010506468 A JP2010506468 A JP 2010506468A JP 2010506468 A JP2010506468 A JP 2010506468A JP 2010536713 A5 JP2010536713 A5 JP 2010536713A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- alkyl group
- alkyl
- alkoxy
- optionally
- 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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- -1 Piperazyl Chemical group 0.000 claims description 53
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 358
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 107
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 89
- 125000002757 morpholinyl group Chemical group 0.000 claims 49
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 45
- 229910052739 hydrogen Inorganic materials 0.000 claims 45
- 239000001257 hydrogen Substances 0.000 claims 45
- 125000004193 piperazinyl group Chemical group 0.000 claims 45
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 40
- 125000002252 acyl group Chemical group 0.000 claims 33
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 33
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 29
- 229910052736 halogen Inorganic materials 0.000 claims 27
- 125000003545 alkoxy group Chemical group 0.000 claims 24
- 150000002367 halogens Chemical class 0.000 claims 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 24
- 125000000217 alkyl group Chemical group 0.000 claims 18
- 125000003277 amino group Chemical group 0.000 claims 17
- 150000002431 hydrogen Chemical class 0.000 claims 17
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims 13
- 150000003839 salts Chemical class 0.000 claims 13
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 12
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims 11
- 125000005936 piperidyl group Chemical group 0.000 claims 11
- 125000004076 pyridyl group Chemical group 0.000 claims 11
- 125000004423 acyloxy group Chemical group 0.000 claims 10
- 125000003118 aryl group Chemical group 0.000 claims 9
- 125000000623 heterocyclic group Chemical group 0.000 claims 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 8
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 8
- 125000002541 furyl group Chemical group 0.000 claims 7
- 125000004043 oxo group Chemical group O=* 0.000 claims 7
- 125000003226 pyrazolyl group Chemical group 0.000 claims 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 7
- 125000001544 thienyl group Chemical group 0.000 claims 7
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 6
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims 6
- 125000005959 diazepanyl group Chemical group 0.000 claims 6
- 125000006239 protecting group Chemical group 0.000 claims 6
- 125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 claims 5
- 125000005236 alkanoylamino group Chemical group 0.000 claims 5
- 125000002393 azetidinyl group Chemical group 0.000 claims 5
- 125000002883 imidazolyl group Chemical group 0.000 claims 5
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims 5
- 125000005961 oxazepanyl group Chemical group 0.000 claims 5
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 5
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 4
- 125000001589 carboacyl group Chemical group 0.000 claims 4
- 125000002768 hydroxyalkyl group Chemical class 0.000 claims 4
- 125000004691 alkyl thio carbonyl group Chemical group 0.000 claims 3
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 3
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical group C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 0 *c(c(*)c1*)c(*)c2c1N(*)C(*)=C(*)C2=O Chemical compound *c(c(*)c1*)c(*)c2c1N(*)C(*)=C(*)C2=O 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- OFOLQTJFUBLDJJ-UHFFFAOYSA-N CC(C)(C)OP(OCN(C=C(c(cc1)ccc1OC)C(c1c(cc2)F)=O)c1c2OCC1CC1)(OC(C)(C)C)=O Chemical compound CC(C)(C)OP(OCN(C=C(c(cc1)ccc1OC)C(c1c(cc2)F)=O)c1c2OCC1CC1)(OC(C)(C)C)=O OFOLQTJFUBLDJJ-UHFFFAOYSA-N 0.000 description 1
- XPNAOQJTFQZVCX-UHFFFAOYSA-N CCCOc(c(OC=C1c(cc2)ccc2OC)c2C1=O)cc1c2OCCC1 Chemical compound CCCOc(c(OC=C1c(cc2)ccc2OC)c2C1=O)cc1c2OCCC1 XPNAOQJTFQZVCX-UHFFFAOYSA-N 0.000 description 1
- XXXCNANYDDICBK-UHFFFAOYSA-N CCCOc(ccc(F)c12)c1N(COO)C=C(c(ccc(OC)c1)c1F)C2=O Chemical compound CCCOc(ccc(F)c12)c1N(COO)C=C(c(ccc(OC)c1)c1F)C2=O XXXCNANYDDICBK-UHFFFAOYSA-N 0.000 description 1
- QRAFLVRADMSZBP-UHFFFAOYSA-N CCOc(ccc(F)c12)c1N(COC(O)(OC(C)(C)C)OC(C)(C)C)C=C(c(c(OC)c1)ccc1OC)C2=O Chemical compound CCOc(ccc(F)c12)c1N(COC(O)(OC(C)(C)C)OC(C)(C)C)C=C(c(c(OC)c1)ccc1OC)C2=O QRAFLVRADMSZBP-UHFFFAOYSA-N 0.000 description 1
- MNYBFDITJKTSSJ-UHFFFAOYSA-N CN(C1CCCCC1)c(c(N(COP(O)(O)=O)C=C1c(cc2)ccc2OC)c2C1=O)ccc2F Chemical compound CN(C1CCCCC1)c(c(N(COP(O)(O)=O)C=C1c(cc2)ccc2OC)c2C1=O)ccc2F MNYBFDITJKTSSJ-UHFFFAOYSA-N 0.000 description 1
- GVZIKOWKPBXZDU-UHFFFAOYSA-N COC1=CC=C(C=C1)C2=C(C(=CC(=C2)C(=O)O)[P+](=O)[O-])OP(=O)(O)O Chemical compound COC1=CC=C(C=C1)C2=C(C(=CC(=C2)C(=O)O)[P+](=O)[O-])OP(=O)(O)O GVZIKOWKPBXZDU-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- ZKBVSKOXBABNKZ-UHFFFAOYSA-N [5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxyquinolin-1-yl]methyl 4-hydroxybenzoate Chemical compound CCCOC1=CC=C(F)C(C(C(C=2C=CC(OC)=CC=2)=C2)=O)=C1N2COC(=O)C1=CC=C(O)C=C1 ZKBVSKOXBABNKZ-UHFFFAOYSA-N 0.000 description 1
- PYXCPXFSPSMOGT-UHFFFAOYSA-N [5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxyquinolin-1-yl]methyl benzoate Chemical compound CCCOC1=CC=C(F)C(C(C(C=2C=CC(OC)=CC=2)=C2)=O)=C1N2COC(=O)C1=CC=CC=C1 PYXCPXFSPSMOGT-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- QOSATHPSBFQAML-UHFFFAOYSA-N hydrogen peroxide;hydrate Chemical compound O.OO QOSATHPSBFQAML-UHFFFAOYSA-N 0.000 description 1
- YGFLCNPXEPDANQ-UHFFFAOYSA-N n-[bis[(2-methylpropan-2-yl)oxy]phosphanyl]-n-propan-2-ylpropan-2-amine Chemical compound CC(C)N(C(C)C)P(OC(C)(C)C)OC(C)(C)C YGFLCNPXEPDANQ-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2010506468A JP5355551B2 (ja) | 2008-12-05 | 2009-12-04 | キノロン化合物及び医薬組成物 |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2008310739 | 2008-12-05 | ||
| JP2008310739 | 2008-12-05 | ||
| PCT/JP2009/070719 WO2010064735A1 (en) | 2008-12-05 | 2009-12-04 | Quinolone compound and pharmaceutical composition |
| JP2010506468A JP5355551B2 (ja) | 2008-12-05 | 2009-12-04 | キノロン化合物及び医薬組成物 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013173042A Division JP2014001227A (ja) | 2008-12-05 | 2013-08-23 | キノロン化合物及び医薬組成物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010536713A JP2010536713A (ja) | 2010-12-02 |
| JP2010536713A5 true JP2010536713A5 (enExample) | 2012-08-09 |
| JP5355551B2 JP5355551B2 (ja) | 2013-11-27 |
Family
ID=41716237
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010506468A Expired - Fee Related JP5355551B2 (ja) | 2008-12-05 | 2009-12-04 | キノロン化合物及び医薬組成物 |
| JP2013173042A Pending JP2014001227A (ja) | 2008-12-05 | 2013-08-23 | キノロン化合物及び医薬組成物 |
| JP2015085167A Withdrawn JP2015157836A (ja) | 2008-12-05 | 2015-04-17 | キノロン化合物及び医薬組成物 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013173042A Pending JP2014001227A (ja) | 2008-12-05 | 2013-08-23 | キノロン化合物及び医薬組成物 |
| JP2015085167A Withdrawn JP2015157836A (ja) | 2008-12-05 | 2015-04-17 | キノロン化合物及び医薬組成物 |
Country Status (28)
| Country | Link |
|---|---|
| US (4) | US8304546B2 (enExample) |
| EP (1) | EP2364298B1 (enExample) |
| JP (3) | JP5355551B2 (enExample) |
| KR (5) | KR20160078518A (enExample) |
| CN (2) | CN103435544A (enExample) |
| AR (1) | AR074486A1 (enExample) |
| AU (1) | AU2009323287B2 (enExample) |
| BR (1) | BRPI0922286A2 (enExample) |
| CA (1) | CA2745019A1 (enExample) |
| CO (1) | CO6331465A2 (enExample) |
| CY (1) | CY1118229T1 (enExample) |
| DK (1) | DK2364298T3 (enExample) |
| ES (1) | ES2594252T3 (enExample) |
| HR (1) | HRP20161209T1 (enExample) |
| HU (1) | HUE029624T2 (enExample) |
| IL (4) | IL212840A0 (enExample) |
| LT (1) | LT2364298T (enExample) |
| MX (1) | MX2011005871A (enExample) |
| MY (1) | MY164007A (enExample) |
| NZ (1) | NZ592881A (enExample) |
| PL (1) | PL2364298T3 (enExample) |
| PT (1) | PT2364298T (enExample) |
| RU (1) | RU2544530C2 (enExample) |
| SI (1) | SI2364298T1 (enExample) |
| TW (2) | TWI492943B (enExample) |
| UA (1) | UA105649C2 (enExample) |
| WO (1) | WO2010064735A1 (enExample) |
| ZA (1) | ZA201103521B (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI366565B (en) * | 2007-06-06 | 2012-06-21 | Otsuka Pharma Co Ltd | Quinolone compound and pharmaceutical composition |
| TWI492943B (zh) * | 2008-12-05 | 2015-07-21 | 大塚製藥股份有限公司 | 喹啉酮化合物及藥學組成物（二） |
| WO2010073078A2 (en) * | 2008-12-22 | 2010-07-01 | Orchid Research Laboratories Ltd. | Heterocyclic compounds as hdac inhibitors |
| JP5769504B2 (ja) * | 2010-06-04 | 2015-08-26 | 大塚製薬株式会社 | 医薬 |
| RU2617512C1 (ru) * | 2015-10-23 | 2017-04-25 | Общество с ограниченной ответственностью "Нормофарм" | Средство с антистрессовой, анксиолитической и антидепрессивной активностью и композиция на его основе |
| EP3414229B1 (en) * | 2016-02-09 | 2021-06-16 | Pharmakea, Inc. | Quinolinone lysyl oxidase-like 2 inhibitors and uses thereof |
| CN106960913A (zh) * | 2017-03-31 | 2017-07-18 | 武汉华星光电技术有限公司 | 量子点发光二极管显示面板及其制备方法 |
| JP2021525741A (ja) | 2018-05-31 | 2021-09-27 | 華領医薬技術（上海）有限公司Ｈｕａ Ｍｅｄｉｃｉｎｅ （Ｓｈａｎｇｈａｉ） Ｌｔｄ． | グルコキナーゼ活性化剤およびｐｐａｒ受容体活性化剤を含む医薬品の組合せ、組成物、配合剤、ならびにその調製方法および使用 |
| JP2023012557A (ja) * | 2020-02-10 | 2023-01-26 | 大塚製薬株式会社 | 新規肝性脳症治療剤 |
Family Cites Families (34)
| Publication number | Priority date | Publication date | Assignee | Title |
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| DE3416695A1 (de) | 1984-05-05 | 1985-11-07 | Bayer Ag, 5090 Leverkusen | Amidinohydrazone von tetralin-, chromon-, thiochromon- und tretrahydrochinolin-derivaten, verfahren zu ihrer herstellung sowie ihre verwendung in arzneimitteln |
| DE3579581D1 (de) * | 1984-12-11 | 1990-10-11 | Siemens Ag | Anordnung zum ankoppeln von betaetigungsvorrichtungen an elektronische naeherungsschalter hierfuer. |
| IL100555A (en) * | 1991-02-07 | 2000-08-31 | Hoechst Marion Roussel Inc | N-substituted quinoline derivatives their preparation their use for the preparation of medicaments and the pharmaceutical compositions containing them |
| MX9200299A (es) | 1991-02-07 | 1992-12-01 | Roussel Uclaf | Nuevos derivados biciclicos nitrogenados, su procedimiento de preparacion los nuevos compuestos intermedios obtenidos su aplicacion como medicamentos y las composiciones farmaceuticas que los contienen. |
| CA2209134A1 (en) | 1994-12-30 | 1996-07-11 | Ligand Pharmaceuticals Incorporated | Tricyclic retinoids, methods for their production and use |
| GB9621757D0 (en) | 1996-10-18 | 1996-12-11 | Ciba Geigy Ag | Phenyl-substituted bicyclic heterocyclyl derivatives and their use |
| WO1998048790A1 (en) | 1997-04-28 | 1998-11-05 | Anticancer, Inc. | Use of genistein and related compounds to treat certain sex hormone related conditions |
| IT1296985B1 (it) | 1997-12-19 | 1999-08-03 | Zambon Spa | Derivati benzazinici inibitori della fosfodiesterasi 4 |
| EP1147094A1 (en) | 1999-01-15 | 2001-10-24 | Novo Nordisk A/S | Non-peptide glp-1 agonists |
| AU4128800A (en) | 1999-04-16 | 2000-11-02 | Astrazeneca Ab | Estrogen receptor-beta ligands |
| JP2002544197A (ja) | 1999-05-06 | 2002-12-24 | ニューロゲン コーポレイション | 置換４−オキソ−キノリン−３−カルボキサミド：ｇａｂａ脳受容体リガンド |
| FR2797444B1 (fr) * | 1999-08-13 | 2003-02-07 | Lafon Labor | Compositions pharmaceutiques comprenant des 4-quinolones |
| AUPQ266199A0 (en) | 1999-09-06 | 1999-09-30 | Novogen Research Pty Ltd | Compositions and therapeutic methods involving isoflavones and analogues thereof |
| FR2813791B1 (fr) | 2000-09-14 | 2004-03-12 | Lafon Labor | Utilisation de 2- et 4-quinolones pour inhiber la neo-proliferation intimale |
| GB0023918D0 (en) | 2000-09-29 | 2000-11-15 | King S College London | Antiparasitic compounds |
| JP2004510815A (ja) | 2000-10-13 | 2004-04-08 | アストラゼネカ・アクチエボラーグ | エストロゲン受容体−βリガンド |
| JP4256679B2 (ja) | 2001-03-16 | 2009-04-22 | ノボゲン リサーチ ピーティーワイ リミテッド | 再狭窄の治療方法 |
| AUPR846401A0 (en) | 2001-10-25 | 2001-11-15 | Novogen Research Pty Ltd | 6-Hydroxy isoflavones, derivatives and medicaments involving same |
| AU2002950217A0 (en) | 2002-07-16 | 2002-09-12 | Prana Biotechnology Limited | 8- Hydroxy Quinoline Derivatives |
| US20050080024A1 (en) | 2002-08-15 | 2005-04-14 | Joseph Tucker | Nitric oxide donating derivatives for the treatment of cardiovascular disorders |
| US20040033480A1 (en) | 2002-08-15 | 2004-02-19 | Wong Norman C.W. | Use of resveratrol to regulate expression of apolipoprotein A1 |
| GB0222516D0 (en) | 2002-09-27 | 2002-11-06 | Karobio Ab | Novel compounds |
| WO2004087160A1 (en) | 2003-04-03 | 2004-10-14 | Prana Biotechnology Ltd | Treatment of neurological conditions |
| WO2004091485A2 (en) | 2003-04-11 | 2004-10-28 | Taigen Biotechnology | Aminoquinoline compounds |
| US20060025337A1 (en) | 2003-07-01 | 2006-02-02 | President And Fellows Of Harvard College | Sirtuin related therapeutics and diagnostics for neurodegenerative diseases |
| CA2541590A1 (en) | 2003-10-10 | 2005-04-21 | Resverlogix Corp. | Treatment of diseases associated with the egr-1 enhancer element |
| CA2542351A1 (en) | 2003-11-19 | 2005-06-02 | Novogen Research Pty Ltd. | Combinational radiotherapy and chemotherapy compositions and methods |
| KR100636423B1 (ko) | 2004-04-30 | 2006-10-19 | 한국화학연구원 | 신규한 퀴놀리논 유도체, 이의 제조방법 및 이를유효성분으로 하는 약학적 조성물 |
| US7846915B2 (en) | 2004-10-20 | 2010-12-07 | Resverlogix Corporation | Stilbenes and chalcones for the prevention and treatment of cardiovascular diseases |
| EP1886996A1 (en) * | 2006-08-10 | 2008-02-13 | Ferrer Internacional, S.A. | 1H-Quinolin-4-one compounds, with affinity for the GABA receptor, processes, uses and compositions |
| TWI366565B (en) * | 2007-06-06 | 2012-06-21 | Otsuka Pharma Co Ltd | Quinolone compound and pharmaceutical composition |
| WO2009053799A1 (en) | 2007-10-24 | 2009-04-30 | Glenmark Pharmaceuticals, S.A. | Novel cannabinoid receptor ligands, pharmaceutical compositions containing them, and process for their preparation |
| ES2546507T3 (es) * | 2008-12-05 | 2015-09-24 | Otsuka Pharmaceutical Co., Ltd. | Agente farmacéutico que comprende un compuesto de quinolona |
| TWI492943B (zh) * | 2008-12-05 | 2015-07-21 | 大塚製藥股份有限公司 | 喹啉酮化合物及藥學組成物（二） |
-
2009
- 2009-12-02 TW TW103145731A patent/TWI492943B/zh not_active IP Right Cessation
- 2009-12-02 TW TW98141152A patent/TWI472525B/zh not_active IP Right Cessation
- 2009-12-04 KR KR1020167016913A patent/KR20160078518A/ko not_active Ceased
- 2009-12-04 KR KR20157007063A patent/KR20150036836A/ko not_active Ceased
- 2009-12-04 KR KR1020127004414A patent/KR101548414B1/ko not_active Expired - Fee Related
- 2009-12-04 MY MYPI2011002462A patent/MY164007A/en unknown
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