JP2013510159A5 - - Google Patents
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- Publication number
- JP2013510159A5 JP2013510159A5 JP2012537955A JP2012537955A JP2013510159A5 JP 2013510159 A5 JP2013510159 A5 JP 2013510159A5 JP 2012537955 A JP2012537955 A JP 2012537955A JP 2012537955 A JP2012537955 A JP 2012537955A JP 2013510159 A5 JP2013510159 A5 JP 2013510159A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- difluoro
- formula
- fluoropyridine
- pyridin
- 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
- 238000000034 method Methods 0.000 claims 15
- 150000001875 compounds Chemical class 0.000 claims 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 5
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- VZFPSCNTFBJZHB-UHFFFAOYSA-N 3-fluoropyridine-2-carbonitrile Chemical compound FC1=CC=CN=C1C#N VZFPSCNTFBJZHB-UHFFFAOYSA-N 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- QLRSPKRGYAGOEC-UHFFFAOYSA-N (3-fluoropyridin-2-yl)methanamine Chemical compound NCC1=NC=CC=C1F QLRSPKRGYAGOEC-UHFFFAOYSA-N 0.000 claims 2
- RTZZBUQTHNQTSR-UHFFFAOYSA-N 2,2-difluoro-2-pyridin-2-ylethanol Chemical compound OCC(F)(F)C1=CC=CC=N1 RTZZBUQTHNQTSR-UHFFFAOYSA-N 0.000 claims 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims 2
- -1 3- fluoro-2-pyridylmethyl Chemical group 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims 2
- 239000007868 Raney catalyst Substances 0.000 claims 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims 2
- 229910000564 Raney nickel Inorganic materials 0.000 claims 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims 2
- 229930195733 hydrocarbon Natural products 0.000 claims 2
- 150000002430 hydrocarbons Chemical class 0.000 claims 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 claims 2
- 150000002576 ketones Chemical class 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- LYGZWKYQIZKXFC-UHFFFAOYSA-N (2,2-difluoro-2-pyridin-2-ylethyl) 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC(F)(F)C1=CC=CC=N1 LYGZWKYQIZKXFC-UHFFFAOYSA-N 0.000 claims 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims 1
- TYKNQWWXUIYRSZ-UHFFFAOYSA-N 2,2-difluoro-2-pyridin-2-ylethanamine Chemical compound NCC(F)(F)C1=CC=CC=N1 TYKNQWWXUIYRSZ-UHFFFAOYSA-N 0.000 claims 1
- UUUYCUQKIMUADO-UHFFFAOYSA-N 2,2-difluoro-2-pyridin-2-ylethanesulfonic acid Chemical compound OS(=O)(=O)CC(F)(F)C1=CC=CC=N1 UUUYCUQKIMUADO-UHFFFAOYSA-N 0.000 claims 1
- JDBIYZFYKSYXPK-UHFFFAOYSA-N 2-chloro-3-ethylpyrazine Chemical compound CCC1=NC=CN=C1Cl JDBIYZFYKSYXPK-UHFFFAOYSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- NVFNJYKITCYHPS-UHFFFAOYSA-N C(C)C1=NC=CN=C1NCC(C1=NC=CC=C1)(F)F Chemical compound C(C)C1=NC=CN=C1NCC(C1=NC=CC=C1)(F)F NVFNJYKITCYHPS-UHFFFAOYSA-N 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical group CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 229940077388 benzenesulfonate Drugs 0.000 claims 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims 1
- 229940011051 isopropyl acetate Drugs 0.000 claims 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN2663CH2009 | 2009-11-03 | ||
| IN2663/CHE/2009 | 2009-11-03 | ||
| PCT/US2010/055176 WO2011056806A1 (en) | 2009-11-03 | 2010-11-02 | Process for the preparation of pyrazinone thrombin inhibitor and its intermediates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2013510159A JP2013510159A (ja) | 2013-03-21 |
| JP2013510159A5 true JP2013510159A5 (cg-RX-API-DMAC7.html) | 2013-12-19 |
Family
ID=43926105
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012537955A Pending JP2013510159A (ja) | 2009-11-03 | 2010-11-02 | ピラジノントロンビン阻害剤およびその中間体の製造方法 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8541580B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP2496087A4 (cg-RX-API-DMAC7.html) |
| JP (1) | JP2013510159A (cg-RX-API-DMAC7.html) |
| KR (1) | KR20120106727A (cg-RX-API-DMAC7.html) |
| CN (1) | CN102711481A (cg-RX-API-DMAC7.html) |
| AU (1) | AU2010315338A1 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2778922A1 (cg-RX-API-DMAC7.html) |
| MX (1) | MX2012005165A (cg-RX-API-DMAC7.html) |
| RU (1) | RU2012118499A (cg-RX-API-DMAC7.html) |
| WO (1) | WO2011056806A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013070623A1 (en) * | 2011-11-07 | 2013-05-16 | Diakron Pharmaceuticals Inc. | An extended release formulation of a direct thrombin inhibitor |
| KR102666624B1 (ko) | 2015-10-26 | 2024-05-16 | 바이엘 크롭사이언스 악티엔게젤샤프트 | 농약으로서의 융합된 비사이클릭 헤테로사이클 유도체 |
| EP3931192B1 (de) | 2019-02-26 | 2024-03-20 | Bayer Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
| CN113710669A (zh) | 2019-02-26 | 2021-11-26 | 拜耳公司 | 作为农药的稠合双环杂环衍生物 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6147078A (en) * | 1998-05-19 | 2000-11-14 | Merck & Co., Inc. | Pyrazinone thrombin inhibitors |
| UA58636C2 (uk) | 1999-06-04 | 2003-08-15 | Мерк Енд Ко., Інк. | Піразинонові інгібітори тромбіну, фармацевтична композиція, спосіб інгібування утворення тромбів у крові, спосіб лікування станів, пов'язаних із тромбоутворенням |
| EP1341784A2 (en) * | 2000-12-06 | 2003-09-10 | Merck & Co., Inc. | Process for making a thrombin inhibitor |
| EP1422221A1 (en) * | 2002-11-20 | 2004-05-26 | Bayer CropScience SA | Novel process for the preparation of 2-aminomethylpyridine derivative |
-
2010
- 2010-11-02 KR KR1020127010789A patent/KR20120106727A/ko not_active Ceased
- 2010-11-02 US US12/938,297 patent/US8541580B2/en not_active Expired - Fee Related
- 2010-11-02 MX MX2012005165A patent/MX2012005165A/es active IP Right Grant
- 2010-11-02 JP JP2012537955A patent/JP2013510159A/ja active Pending
- 2010-11-02 CN CN2010800499062A patent/CN102711481A/zh active Pending
- 2010-11-02 WO PCT/US2010/055176 patent/WO2011056806A1/en not_active Ceased
- 2010-11-02 AU AU2010315338A patent/AU2010315338A1/en not_active Abandoned
- 2010-11-02 RU RU2012118499/04A patent/RU2012118499A/ru not_active Application Discontinuation
- 2010-11-02 CA CA2778922A patent/CA2778922A1/en not_active Abandoned
- 2010-11-02 EP EP10828989.3A patent/EP2496087A4/en not_active Withdrawn