JP2008526910A5 - - Google Patents
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- Publication number
- JP2008526910A5 JP2008526910A5 JP2007550751A JP2007550751A JP2008526910A5 JP 2008526910 A5 JP2008526910 A5 JP 2008526910A5 JP 2007550751 A JP2007550751 A JP 2007550751A JP 2007550751 A JP2007550751 A JP 2007550751A JP 2008526910 A5 JP2008526910 A5 JP 2008526910A5
- Authority
- JP
- Japan
- Prior art keywords
- mmol
- acid
- colorless oil
- hplc
- methoxy
- 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.)
- Pending
Links
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
- 239000012230 colorless oil Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 3
- 235000019439 ethyl acetate Nutrition 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- JDFDHBSESGTDAL-UHFFFAOYSA-N 3-methoxypropan-1-ol Chemical compound COCCCO JDFDHBSESGTDAL-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VREWSCMOGIXMDQ-UHFFFAOYSA-N (2,3-dimethoxyphenyl)boronic acid Chemical compound COC1=CC=CC(B(O)O)=C1OC VREWSCMOGIXMDQ-UHFFFAOYSA-N 0.000 description 1
- PVIGUZZDWGININ-UHFFFAOYSA-N 1-(bromomethyl)-2,3-dichlorobenzene Chemical compound ClC1=CC=CC(CBr)=C1Cl PVIGUZZDWGININ-UHFFFAOYSA-N 0.000 description 1
- LQMZSVRCDYSUIJ-UHFFFAOYSA-N 1-o-tert-butyl 5-o-methyl 4-(trifluoromethylsulfonyloxy)-3,6-dihydro-2h-pyridine-1,5-dicarboxylate Chemical compound COC(=O)C1=C(OS(=O)(=O)C(F)(F)F)CCN(C(=O)OC(C)(C)C)C1 LQMZSVRCDYSUIJ-UHFFFAOYSA-N 0.000 description 1
- HKHWSBKZTODSDF-UHFFFAOYSA-N 2-chloro-6-(3-methoxypropoxy)pyridine-4-carboxylic acid Chemical compound COCCCOC1=CC(C(O)=O)=CC(Cl)=N1 HKHWSBKZTODSDF-UHFFFAOYSA-N 0.000 description 1
- ICNCOMYUODLTAI-UHFFFAOYSA-N 2-chloroquinoline-4-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC(Cl)=NC2=C1 ICNCOMYUODLTAI-UHFFFAOYSA-N 0.000 description 1
- -1 3-methoxy - propoxy Chemical group 0.000 description 1
- 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 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- DDKMFOUTRRODRE-UHFFFAOYSA-N chloromethanone Chemical compound Cl[C]=O DDKMFOUTRRODRE-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0500784.4A GB0500784D0 (en) | 2005-01-14 | 2005-01-14 | Organic compounds |
| PCT/EP2006/000216 WO2006074924A1 (en) | 2005-01-14 | 2006-01-12 | 3,4,(5)-substituted tetrahvdropyridines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008526910A JP2008526910A (ja) | 2008-07-24 |
| JP2008526910A5 true JP2008526910A5 (enExample) | 2009-02-26 |
Family
ID=34224619
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007550751A Pending JP2008526910A (ja) | 2005-01-14 | 2006-01-12 | ３，４，（５）−置換テトラヒドロピリジン |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US20100029647A1 (enExample) |
| EP (1) | EP1841740A1 (enExample) |
| JP (1) | JP2008526910A (enExample) |
| KR (1) | KR20070094918A (enExample) |
| CN (1) | CN101103002A (enExample) |
| AU (1) | AU2006205877B2 (enExample) |
| BR (1) | BRPI0606321A2 (enExample) |
| CA (1) | CA2590898A1 (enExample) |
| GB (1) | GB0500784D0 (enExample) |
| MX (1) | MX2007008558A (enExample) |
| RU (1) | RU2007130791A (enExample) |
| WO (1) | WO2006074924A1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0505969D0 (en) * | 2005-03-23 | 2005-04-27 | Novartis Ag | Organic compounds |
| GB0514203D0 (en) | 2005-07-11 | 2005-08-17 | Novartis Ag | Organic compounds |
| US8129411B2 (en) | 2005-12-30 | 2012-03-06 | Novartis Ag | Organic compounds |
| EP1908471A1 (en) * | 2006-10-04 | 2008-04-09 | Speedel Experimenta AG | Tetrahydropyridines as renin inhibitors |
| US8129538B1 (en) | 2007-03-28 | 2012-03-06 | Takeda Pharmaceutical Company Limited | Renin inhibitors |
| CA2689109A1 (en) | 2007-06-25 | 2008-12-31 | Novartis Ag | N5-(2-ethoxyethyl)-n3-(2-pyridinyl) -3,5-piperidinedicarboxamide derivatives for use as renin inhibitors |
| KR101403311B1 (ko) | 2008-05-05 | 2014-06-05 | 액테리온 파마슈티칼 리미티드 | 레닌 억제제로서의 3,4-치환된 피페리딘 유도체 |
| US8586776B2 (en) | 2009-11-05 | 2013-11-19 | Fibrostatin, S.L. | GPBP inhibition using Q2 peptidomimetics |
| CN103502221B (zh) | 2011-03-18 | 2016-03-30 | 拜耳知识产权有限责任公司 | N-(3-氨甲酰基苯基)-1h-吡唑-5-甲酰胺衍生物及其用于防治动物害虫的用途 |
| EP2933248B1 (en) * | 2012-09-14 | 2018-01-31 | Mitsubishi Tanabe Pharma Corporation | Novel renin inhibitor |
| WO2016114312A1 (ja) | 2015-01-13 | 2016-07-21 | 日産化学工業株式会社 | 反応混合物中のスズ化合物の処理方法 |
| CN110577974B (zh) * | 2019-09-10 | 2021-07-20 | 杭州澳赛诺生物科技有限公司 | 手性3-羟基-1,2,3,6-四氢吡啶的合成方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE242213T1 (de) * | 1995-09-07 | 2003-06-15 | Hoffmann La Roche | Neue 4-(oxyalkoxyphenyl)-3-oxy-piperidine zur behandlung von herz- und niereninsuffizienz |
| US6376672B1 (en) * | 1999-04-27 | 2002-04-23 | Hoffmann-La Roche Inc. | Naphthalenylmethoxypiperidines as renin inhibitors |
| US6197959B1 (en) * | 1999-04-27 | 2001-03-06 | Hoffmann-La Roche Inc. | Piperidine derivatives |
| EP1505945B1 (en) * | 2002-05-20 | 2008-11-05 | Bristol-Myers Squibb Company | Substituted cycloalkyl p1' hepatitis c virus inhibitors |
| CA2490138A1 (en) * | 2002-06-27 | 2004-01-08 | Actelion Pharmaceuticals Ltd. | Novel tetrahydropyridine derivatives as renin inhibitors |
| MXPA05011478A (es) * | 2003-04-29 | 2005-12-12 | Actelion Pharmaceuticals Ltd | Derivados de 1,2,3,6-tetrahidropiridina 3,4-disustituidos novedosos. |
| WO2005040120A1 (en) * | 2003-10-09 | 2005-05-06 | Actelion Pharmaceuticals Ltd | Tetrahydropyridine derivatives |
-
2005
- 2005-01-14 GB GBGB0500784.4A patent/GB0500784D0/en not_active Ceased
-
2006
- 2006-01-12 EP EP06700380A patent/EP1841740A1/en not_active Withdrawn
- 2006-01-12 CN CNA2006800023806A patent/CN101103002A/zh active Pending
- 2006-01-12 MX MX2007008558A patent/MX2007008558A/es not_active Application Discontinuation
- 2006-01-12 RU RU2007130791/04A patent/RU2007130791A/ru not_active Application Discontinuation
- 2006-01-12 BR BRPI0606321-7A patent/BRPI0606321A2/pt not_active IP Right Cessation
- 2006-01-12 JP JP2007550751A patent/JP2008526910A/ja active Pending
- 2006-01-12 US US11/722,398 patent/US20100029647A1/en not_active Abandoned
- 2006-01-12 AU AU2006205877A patent/AU2006205877B2/en not_active Expired - Fee Related
- 2006-01-12 WO PCT/EP2006/000216 patent/WO2006074924A1/en not_active Ceased
- 2006-01-12 CA CA002590898A patent/CA2590898A1/en not_active Abandoned
- 2006-01-12 KR KR1020077016005A patent/KR20070094918A/ko not_active Withdrawn
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