JP2010536713A5 - - Google Patents
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- 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
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- 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.)
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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 | ||
| JP2010506468A JP5355551B2 (ja) | 2008-12-05 | 2009-12-04 | キノロン化合物及び医薬組成物 |
| PCT/JP2009/070719 WO2010064735A1 (en) | 2008-12-05 | 2009-12-04 | Quinolone compound and pharmaceutical composition |
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 (cg-RX-API-DMAC7.html) | 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)
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 |
| TWI472525B (zh) | 2008-12-05 | 2015-02-11 | Otsuka Pharma Co Ltd | 喹啉酮化合物及藥學組成物 |
| 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 |
| AU2017218889A1 (en) * | 2016-02-09 | 2018-08-30 | 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 |
| EP3811939A4 (en) | 2018-05-31 | 2022-05-25 | Hua Medicine (Shanghai) Ltd. | PHARMACEUTICAL COMBINATION, COMPOSITION AND FORMULATION CONTAINING A GLUCOSIDASE ACTIVATOR AND A &X3B1;-GLUCOSIDASE INHIBITOR, METHODS OF PREPARING THEM AND USES THEREOF |
| 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 |
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| DE3579581D1 (de) * | 1984-12-11 | 1990-10-11 | Siemens Ag | Anordnung zum ankoppeln von betaetigungsvorrichtungen an elektronische naeherungsschalter hierfuer. |
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| AU3033500A (en) | 1999-01-15 | 2000-08-01 | Agouron Pharmaceuticals, Inc. | Non-peptide glp-1 agonists |
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| KR20110096143A (ko) * | 2008-12-05 | 2011-08-29 | 오츠카 세이야쿠 가부시키가이샤 | 퀴놀론 화합물을 포함하는 약제 |
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2009
- 2009-12-02 TW TW98141152A patent/TWI472525B/zh not_active IP Right Cessation
- 2009-12-02 TW TW103145731A patent/TWI492943B/zh not_active IP Right Cessation
- 2009-12-04 SI SI200931526A patent/SI2364298T1/sl unknown
- 2009-12-04 NZ NZ59288109A patent/NZ592881A/xx unknown
- 2009-12-04 LT LTEP09804077.7T patent/LT2364298T/lt unknown
- 2009-12-04 RU RU2011127404/04A patent/RU2544530C2/ru not_active IP Right Cessation
- 2009-12-04 CA CA 2745019 patent/CA2745019A1/en not_active Abandoned
- 2009-12-04 CN CN200980148815.1A patent/CN102239147B/zh not_active Expired - Fee Related
- 2009-12-04 AR ARP090104715 patent/AR074486A1/es unknown
- 2009-12-04 UA UAA201108418A patent/UA105649C2/uk unknown
- 2009-12-04 PL PL09804077T patent/PL2364298T3/pl unknown
- 2009-12-04 WO PCT/JP2009/070719 patent/WO2010064735A1/en not_active Ceased
- 2009-12-04 US US14/038,862 patent/USRE45108E1/en not_active Expired - Fee Related
- 2009-12-04 MY MYPI2011002462A patent/MY164007A/en unknown
- 2009-12-04 KR KR1020127004414A patent/KR101548414B1/ko not_active Expired - Fee Related
- 2009-12-04 CN CN2013103178088A patent/CN103435544A/zh active Pending
- 2009-12-04 JP JP2010506468A patent/JP5355551B2/ja not_active Expired - Fee Related
- 2009-12-04 KR KR1020127027782A patent/KR101662362B1/ko not_active Expired - Fee Related
- 2009-12-04 PT PT98040777T patent/PT2364298T/pt unknown
- 2009-12-04 AU AU2009323287A patent/AU2009323287B2/en not_active Ceased
- 2009-12-04 MX MX2011005871A patent/MX2011005871A/es active IP Right Grant
- 2009-12-04 HU HUE09804077A patent/HUE029624T2/en unknown
- 2009-12-04 ES ES09804077.7T patent/ES2594252T3/es active Active
- 2009-12-04 BR BRPI0922286A patent/BRPI0922286A2/pt not_active IP Right Cessation
- 2009-12-04 HR HRP20161209TT patent/HRP20161209T1/hr unknown
- 2009-12-04 KR KR1020167016913A patent/KR20160078518A/ko not_active Ceased
- 2009-12-04 KR KR20107002390A patent/KR101278383B1/ko not_active Expired - Fee Related
- 2009-12-04 KR KR20157007063A patent/KR20150036836A/ko not_active Ceased
- 2009-12-04 DK DK09804077.7T patent/DK2364298T3/en active
- 2009-12-04 EP EP09804077.7A patent/EP2364298B1/en not_active Not-in-force
- 2009-12-04 US US12/668,164 patent/US8304546B2/en not_active Ceased
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2011
- 2011-05-12 IL IL212840A patent/IL212840A0/en unknown
- 2011-05-13 ZA ZA2011/03521A patent/ZA201103521B/en unknown
- 2011-07-05 CO CO11083156A patent/CO6331465A2/es not_active Application Discontinuation
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2012
- 2012-09-14 US US13/616,740 patent/US8592593B2/en not_active Expired - Fee Related
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2013
- 2013-08-23 JP JP2013173042A patent/JP2014001227A/ja active Pending
- 2013-10-18 US US14/057,599 patent/US9018229B2/en not_active Expired - Fee Related
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2014
- 2014-05-05 IL IL232458A patent/IL232458A0/en unknown
- 2014-05-05 IL IL232457A patent/IL232457A0/en unknown
- 2014-05-05 IL IL232459A patent/IL232459A0/en unknown
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2015
- 2015-04-17 JP JP2015085167A patent/JP2015157836A/ja not_active Withdrawn
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2016
- 2016-10-03 CY CY20161100980T patent/CY1118229T1/el unknown