JP2013544796A5 - - Google Patents
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- Publication number
- JP2013544796A5 JP2013544796A5 JP2013534440A JP2013534440A JP2013544796A5 JP 2013544796 A5 JP2013544796 A5 JP 2013544796A5 JP 2013534440 A JP2013534440 A JP 2013534440A JP 2013534440 A JP2013534440 A JP 2013534440A JP 2013544796 A5 JP2013544796 A5 JP 2013544796A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- phenyl
- group
- dioxaspiro
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims 29
- 238000000034 method Methods 0.000 claims 10
- 125000003118 aryl group Chemical group 0.000 claims 7
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 125000004185 ester group Chemical group 0.000 claims 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- -1 decan-7-yl Chemical group 0.000 claims 4
- 238000007363 ring formation reaction Methods 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 2
- 230000008030 elimination Effects 0.000 claims 2
- 238000003379 elimination reaction Methods 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- OIOPYOWOWQCDBO-UHFFFAOYSA-N 2-(1,4-dioxaspiro[4.5]decan-7-yl)-2-phenylacetaldehyde Chemical compound C=1C=CC=CC=1C(C=O)C(C1)CCCC21OCCO2 OIOPYOWOWQCDBO-UHFFFAOYSA-N 0.000 claims 1
- OTAQZHKYQWYETL-UHFFFAOYSA-N 2-(1,4-dioxaspiro[4.5]decan-7-yl)-2-phenylethanol Chemical compound C=1C=CC=CC=1C(CO)C(C1)CCCC21OCCO2 OTAQZHKYQWYETL-UHFFFAOYSA-N 0.000 claims 1
- OIOPYOWOWQCDBO-GICMACPYSA-N 2-[(7r)-1,4-dioxaspiro[4.5]decan-7-yl]-2-phenylacetaldehyde Chemical compound C([C@H](C1)C(C=O)C=2C=CC=CC=2)CCC21OCCO2 OIOPYOWOWQCDBO-GICMACPYSA-N 0.000 claims 1
- OTAQZHKYQWYETL-GICMACPYSA-N 2-[(7r)-1,4-dioxaspiro[4.5]decan-7-yl]-2-phenylethanol Chemical compound C([C@H](C1)C(CO)C=2C=CC=CC=2)CCC21OCCO2 OTAQZHKYQWYETL-GICMACPYSA-N 0.000 claims 1
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical class CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 claims 1
- KIBMFRVIMWZATK-AYRXBEOTSA-N [(1r,2s,3s,4r)-5-oxo-2-phenyl-3-bicyclo[2.2.2]octanyl] methanesulfonate Chemical compound C1([C@H]2[C@H](OS(C)(=O)=O)[C@]3(CC[C@@]2(CC3=O)[H])[H])=CC=CC=C1 KIBMFRVIMWZATK-AYRXBEOTSA-N 0.000 claims 1
- PEBSFLONQDNKQK-PHLCOOFXSA-N [(1r,4r,5r)-5-[2-[3-(4,7-dimethoxy-1h-benzimidazol-2-yl)propyl-methylamino]ethyl]-2-phenyl-5-bicyclo[2.2.2]oct-2-enyl] 2-methylpropanoate Chemical compound C([C@]1(CC[C@@]2(C[C@]1(CCN(C)CCCC=1NC3=C(OC)C=CC(OC)=C3N=1)OC(=O)C(C)C)[H])[H])=C2C1=CC=CC=C1 PEBSFLONQDNKQK-PHLCOOFXSA-N 0.000 claims 1
- PEBSFLONQDNKQK-UTKFAANNSA-N [(1s,4s,5s)-5-[2-[3-(4,7-dimethoxy-1h-benzimidazol-2-yl)propyl-methylamino]ethyl]-2-phenyl-5-bicyclo[2.2.2]oct-2-enyl] 2-methylpropanoate Chemical compound C([C@@]1(CC[C@]2(C[C@@]1(CCN(C)CCCC=1NC3=C(OC)C=CC(OC)=C3N=1)OC(=O)C(C)C)[H])[H])=C2C1=CC=CC=C1 PEBSFLONQDNKQK-UTKFAANNSA-N 0.000 claims 1
- 238000006254 arylation reaction Methods 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- HAQRDXCLYFVXIA-UHFFFAOYSA-N methyl 2-(1,4-dioxaspiro[4.5]decan-7-yl)-2-phenylacetate Chemical compound C=1C=CC=CC=1C(C(=O)OC)C(C1)CCCC21OCCO2 HAQRDXCLYFVXIA-UHFFFAOYSA-N 0.000 claims 1
- HAQRDXCLYFVXIA-GICMACPYSA-N methyl 2-[(7r)-1,4-dioxaspiro[4.5]decan-7-yl]-2-phenylacetate Chemical compound C([C@H](C1)C(C(=O)OC)C=2C=CC=CC=2)CCC21OCCO2 HAQRDXCLYFVXIA-GICMACPYSA-N 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- 230000007704 transition Effects 0.000 claims 1
- 0 CN(C)C(CC#O)(CCC1)CC1(*)*=C Chemical compound CN(C)C(CC#O)(CCC1)CC1(*)*=C 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IB2010054747 | 2010-10-20 | ||
| IBPCT/IB2010/054747 | 2010-10-20 | ||
| PCT/IB2011/054660 WO2012052939A2 (en) | 2010-10-20 | 2011-10-19 | Preparation of bicyclo[2.2.2]octan-2-one compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013544796A JP2013544796A (ja) | 2013-12-19 |
| JP2013544796A5 true JP2013544796A5 (enExample) | 2014-12-04 |
| JP5909237B2 JP5909237B2 (ja) | 2016-04-26 |
Family
ID=45757740
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013534440A Expired - Fee Related JP5909237B2 (ja) | 2010-10-20 | 2011-10-19 | ビシクロ［２．２．２］オクタン−２−オン化合物の製造 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US9296673B2 (enExample) |
| EP (1) | EP2630111B1 (enExample) |
| JP (1) | JP5909237B2 (enExample) |
| KR (1) | KR101876594B1 (enExample) |
| CN (1) | CN103168019B (enExample) |
| CA (1) | CA2813131C (enExample) |
| DK (1) | DK2630111T3 (enExample) |
| ES (1) | ES2536897T3 (enExample) |
| HU (1) | HUE025195T2 (enExample) |
| IL (1) | IL225763A (enExample) |
| MX (1) | MX2013004427A (enExample) |
| TW (2) | TWI511949B (enExample) |
| WO (1) | WO2012052939A2 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012052939A2 (en) * | 2010-10-20 | 2012-04-26 | Actelion Pharmaceuticals Ltd | Preparation of bicyclo[2.2.2]octan-2-one compounds |
| DK2630120T3 (en) | 2010-10-20 | 2018-10-08 | Idorsia Pharmaceuticals Ltd | DIASTEREOSELECTIVE PREPARATION OF BICYCLO [2.2.2] OCTAN-2-ON COMPOUNDS |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3046106A1 (de) | 1980-12-06 | 1982-07-15 | Studiengesellschaft Kohle mbH, 4330 Mülheim | Optisch reine bicyclo(2.2.2)oct-5-en-2.one, verfahren zu ihrer herstellung und ihre verwendung |
| JP3439255B2 (ja) * | 1994-03-31 | 2003-08-25 | 長瀬産業株式会社 | 不斉マイケル反応を触媒する金属錯体 |
| CL2008001205A1 (es) | 2007-04-27 | 2008-11-14 | Actelion Pharmaceuticals Ltd | Compuestos derivados de biciclo[2.2.2]octeno; composicion farmaceutica que los contiene; y uso en el tratamiento o prevencion de angina cronica estable, hipertension, isquemia renal y cardiaca, arritmias cardiacas, hipertrofia cardiaca y falla congestiva del corazon. |
| AU2009239620A1 (en) | 2008-04-25 | 2009-10-29 | Actelion Pharmaceuticals Ltd | Benzimidazole derivatives as calcium channel blockers |
| WO2012052939A2 (en) * | 2010-10-20 | 2012-04-26 | Actelion Pharmaceuticals Ltd | Preparation of bicyclo[2.2.2]octan-2-one compounds |
| DK2630120T3 (en) | 2010-10-20 | 2018-10-08 | Idorsia Pharmaceuticals Ltd | DIASTEREOSELECTIVE PREPARATION OF BICYCLO [2.2.2] OCTAN-2-ON COMPOUNDS |
-
2011
- 2011-10-19 WO PCT/IB2011/054660 patent/WO2012052939A2/en not_active Ceased
- 2011-10-19 EP EP11820867.7A patent/EP2630111B1/en active Active
- 2011-10-19 MX MX2013004427A patent/MX2013004427A/es active IP Right Grant
- 2011-10-19 US US13/880,520 patent/US9296673B2/en not_active Expired - Fee Related
- 2011-10-19 JP JP2013534440A patent/JP5909237B2/ja not_active Expired - Fee Related
- 2011-10-19 TW TW100137956A patent/TWI511949B/zh not_active IP Right Cessation
- 2011-10-19 CA CA2813131A patent/CA2813131C/en active Active
- 2011-10-19 CN CN201180050144.2A patent/CN103168019B/zh not_active Expired - Fee Related
- 2011-10-19 DK DK11820867.7T patent/DK2630111T3/en active
- 2011-10-19 HU HUE11820867A patent/HUE025195T2/en unknown
- 2011-10-19 TW TW100137955A patent/TWI551583B/zh not_active IP Right Cessation
- 2011-10-19 ES ES11820867.7T patent/ES2536897T3/es active Active
- 2011-10-19 KR KR1020137012606A patent/KR101876594B1/ko not_active Expired - Fee Related
-
2013
- 2013-04-15 IL IL225763A patent/IL225763A/en active IP Right Grant
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