JP2019529459A5 - - Google Patents
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- JP2019529459A5 JP2019529459A5 JP2019515915A JP2019515915A JP2019529459A5 JP 2019529459 A5 JP2019529459 A5 JP 2019529459A5 JP 2019515915 A JP2019515915 A JP 2019515915A JP 2019515915 A JP2019515915 A JP 2019515915A JP 2019529459 A5 JP2019529459 A5 JP 2019529459A5
- Authority
- JP
- Japan
- Prior art keywords
- mmol
- mixture
- stirred
- trifluorophenyl
- solution
- 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.)
- Ceased
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 18
- 239000000243 solution Substances 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- -1 (S) -1- Butyl -6- (3,5-difluorophenyl) -6,7-dihydro-2H-pyrrolo [1,2-c] imidazole-3 (5H) -thione 4- (3,5-difluorophenyl) -2-pentanoylpyrrolidine-1-carboxylic acid Chemical compound 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000000843 powder Substances 0.000 description 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- YSCQMDHOZCTUHC-UHFFFAOYSA-N 2-methoxy-4-(2,3,6-trifluorophenyl)pyrrolidine-1-carboxylic acid Chemical compound COC1CC(CN1C(O)=O)c1c(F)ccc(F)c1F YSCQMDHOZCTUHC-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- QCJWPKRFBPIJON-WSAWMEMJSA-N (4R)-2-oxo-4-(2,3,6-trifluorophenyl)pyrrolidine-3-carboxylic acid Chemical compound O=C1NC[C@H](C1C(=O)O)C1=C(C(=CC=C1F)F)F QCJWPKRFBPIJON-WSAWMEMJSA-N 0.000 description 2
- RVTSBQGJXJVXEG-YFKPBYRVSA-N (4R)-4-(2,3,6-trifluorophenyl)pyrrolidin-2-one Chemical compound FC1=C(C(=CC=C1F)F)[C@H]1CC(NC1)=O RVTSBQGJXJVXEG-YFKPBYRVSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 2
- RKPIXVUPPPCHAN-ZETCQYMHSA-N (6R)-1-methyl-6-(2,3,6-trifluorophenyl)-2,5,6,7-tetrahydropyrrolo[1,2-c]imidazole-3-thione Chemical compound Cc1[nH]c(=S)n2C[C@H](Cc12)c1c(F)ccc(F)c1F RKPIXVUPPPCHAN-ZETCQYMHSA-N 0.000 description 1
- CGIPRUJNLUOBAN-ONEGZZNKSA-N 1,2,4-trifluoro-3-[(E)-2-nitroethenyl]benzene Chemical compound [O-][N+](=O)\C=C\C1=C(F)C=CC(F)=C1F CGIPRUJNLUOBAN-ONEGZZNKSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VUZPGEIXNYGDJN-UHFFFAOYSA-N 1-nitroethanol Chemical compound CC(O)[N+]([O-])=O VUZPGEIXNYGDJN-UHFFFAOYSA-N 0.000 description 1
- IWAMIZNQNATIKJ-UHFFFAOYSA-N 2-(3-bromo-2,6-difluorophenyl)acetonitrile Chemical compound FC1=CC=C(Br)C(F)=C1CC#N IWAMIZNQNATIKJ-UHFFFAOYSA-N 0.000 description 1
- WLUXSIMCNOXENF-UHFFFAOYSA-N 2-[2-nitro-1-(2,3,6-trifluorophenyl)ethyl]propanedioic acid Chemical compound [N+](=O)([O-])CC(C1=C(C(=CC=C1F)F)F)C(C(=O)O)C(=O)O WLUXSIMCNOXENF-UHFFFAOYSA-N 0.000 description 1
- QCJWPKRFBPIJON-UHFFFAOYSA-N 2-oxo-4-(2,3,6-trifluorophenyl)pyrrolidine-3-carboxylic acid Chemical compound OC(=O)C1C(CNC1=O)c1c(F)ccc(F)c1F QCJWPKRFBPIJON-UHFFFAOYSA-N 0.000 description 1
- XBLGJUZMAFLWBI-UHFFFAOYSA-N O=C1N(CC(C1)C1=C(C(=CC=C1F)F)F)C(=O)O Chemical compound O=C1N(CC(C1)C1=C(C(=CC=C1F)F)F)C(=O)O XBLGJUZMAFLWBI-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000004687 hexahydrates Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 229940116357 potassium thiocyanate Drugs 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB1616201.8A GB201616201D0 (en) | 2016-09-23 | 2016-09-23 | Blood-brain barrier-penetrant dopamine-B-hydroxylase inhibitors |
| GB1616201.8 | 2016-09-23 | ||
| GBGB1713779.5A GB201713779D0 (en) | 2017-08-29 | 2017-08-29 | Blood-brain barrier-penetrant dopamine B-hydroxylase inhibitors |
| GB1713779.5 | 2017-08-29 | ||
| PCT/PT2017/050023 WO2018056855A1 (en) | 2016-09-23 | 2017-09-22 | Dopamine-b-hydroxylase inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2019529459A JP2019529459A (ja) | 2019-10-17 |
| JP2019529459A5 true JP2019529459A5 (OSRAM) | 2021-10-14 |
Family
ID=60009687
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019515929A Pending JP2019529460A (ja) | 2016-09-23 | 2017-09-22 | 血管脳関門透過剤ドーパミン−ｂ−ヒドロキシラーゼ阻害剤 |
| JP2019515915A Ceased JP2019529459A (ja) | 2016-09-23 | 2017-09-22 | ドーパミン−ｂ−ヒドロキシラーゼ阻害剤 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019515929A Pending JP2019529460A (ja) | 2016-09-23 | 2017-09-22 | 血管脳関門透過剤ドーパミン−ｂ−ヒドロキシラーゼ阻害剤 |
Country Status (20)
| Country | Link |
|---|---|
| US (3) | US10975083B2 (OSRAM) |
| EP (2) | EP3515433A1 (OSRAM) |
| JP (2) | JP2019529460A (OSRAM) |
| KR (2) | KR20190076967A (OSRAM) |
| CN (2) | CN109715633B (OSRAM) |
| AU (2) | AU2017330175B2 (OSRAM) |
| BR (2) | BR112019004248A2 (OSRAM) |
| CA (2) | CA3036650A1 (OSRAM) |
| CL (2) | CL2019000661A1 (OSRAM) |
| CO (2) | CO2019002523A2 (OSRAM) |
| IL (2) | IL265139B (OSRAM) |
| JO (2) | JOP20190049A1 (OSRAM) |
| MA (2) | MA46280A (OSRAM) |
| MX (2) | MX384293B (OSRAM) |
| PE (2) | PE20191103A1 (OSRAM) |
| PH (2) | PH12019500568A1 (OSRAM) |
| SG (2) | SG11201901817SA (OSRAM) |
| TW (2) | TW201817713A (OSRAM) |
| UA (2) | UA123071C2 (OSRAM) |
| WO (2) | WO2018056854A1 (OSRAM) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JOP20190049A1 (ar) | 2016-09-23 | 2019-03-20 | Bial Portela & C? S A | مثبطات دوبامين-b-هيدروكسيلاز |
| JOP20190107A1 (ar) | 2016-11-16 | 2019-05-09 | Lundbeck La Jolla Research Center Inc | مثبطات أحادي أسيل جليسرول ليباز (magl) |
| PE20200664A1 (es) | 2017-08-29 | 2020-06-11 | Lundbeck La Jolla Research Center Inc | Compuestos espirociclicos y sus metodos de preparacion y uso |
| SG11202004231YA (en) | 2017-12-04 | 2020-06-29 | BIAL PORTELA & Cª S A | Dopamine-β-hydroxylase inhibitors |
| GB201908044D0 (en) | 2019-06-05 | 2019-07-17 | Bial Portela & Ca Sa | Dopamine-B-Hydroxylase inhibitors |
| CN111675654A (zh) * | 2020-07-22 | 2020-09-18 | 南开大学 | 一种以惰性环丙烷为原料合成四氢喹啉类化合物的方法 |
| CN113354620B (zh) * | 2021-07-05 | 2022-03-22 | 南京桦冠生物技术有限公司 | 一种特地唑胺中间体的高效制备方法及其中间体 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3647790A (en) * | 1969-04-08 | 1972-03-07 | American Home Prod | Ouinoxalinyl-oxazolidines and -oxazines |
| ES378317A1 (es) * | 1969-04-11 | 1972-06-01 | Robins Co Inc A H | Un procedimiento para la preparacion de 3-fenilpirrolidinas1-sustituidas. |
| FR2449689A1 (fr) * | 1979-02-20 | 1980-09-19 | Logeais Labor Jacques | Nouveaux derives condenses de pyrrolidine ou de piperidine, leur procede de preparation et leurs applications en therapeutique |
| US4728741A (en) * | 1985-01-08 | 1988-03-01 | Smithkline Beckman Corporation | 1-substituted-2-mercapto benzimidazole compounds and intermediates |
| EP0484437A4 (en) * | 1989-07-27 | 1994-06-01 | Searle & Co | Renal-selective prodrugs for the treatment of hypertension |
| JPH07173143A (ja) * | 1993-12-17 | 1995-07-11 | Wakamoto Pharmaceut Co Ltd | 新規２−チオキソ−４−チアゾリジノン誘導体及び医薬 |
| CZ290082B6 (cs) | 1994-04-26 | 2002-05-15 | Syntex (U. S. A.) Inc. | Benzocykloalkylazolthionové deriváty, farmaceutický prostředek je obsahující, způsob jejich přípravy a meziprodukty přípravy |
| US6482982B1 (en) * | 2001-03-09 | 2002-11-19 | University Of Sciences Of Philadelphia | Halogenated antituberculosis agents |
| US7125904B2 (en) * | 2002-10-11 | 2006-10-24 | Portela & C.A., S.A. | Peripherally-selective inhibitors of dopamine-β-hydroxylase and method of their preparation |
| WO2008085008A1 (en) * | 2007-01-11 | 2008-07-17 | Mogam Biotechnology Research Institute | T-cell inhibiting compounds and their use for the treatment of t-cell-mediated diseases |
| GB0708818D0 (en) * | 2007-05-08 | 2007-06-13 | Portela & Ca Sa | Compounds |
| JP2010534676A (ja) | 2007-07-23 | 2010-11-11 | シノシア・セラピューティクス | 心的外傷後ストレス障害の治療 |
| CN105263910A (zh) * | 2013-02-18 | 2016-01-20 | 斯克利普斯研究所 | 具有治疗潜力的血管加压素受体调节剂 |
| JOP20190049A1 (ar) * | 2016-09-23 | 2019-03-20 | Bial Portela & C? S A | مثبطات دوبامين-b-هيدروكسيلاز |
-
2017
- 2017-06-16 JO JOP/2019/0049A patent/JOP20190049A1/ar unknown
- 2017-06-16 JO JOP/2019/0050A patent/JOP20190050A1/ar unknown
- 2017-09-22 US US16/335,521 patent/US10975083B2/en not_active Expired - Fee Related
- 2017-09-22 BR BR112019004248A patent/BR112019004248A2/pt not_active IP Right Cessation
- 2017-09-22 PE PE2019000691A patent/PE20191103A1/es unknown
- 2017-09-22 CA CA3036650A patent/CA3036650A1/en not_active Abandoned
- 2017-09-22 AU AU2017330175A patent/AU2017330175B2/en not_active Expired - Fee Related
- 2017-09-22 WO PCT/PT2017/050022 patent/WO2018056854A1/en not_active Ceased
- 2017-09-22 WO PCT/PT2017/050023 patent/WO2018056855A1/en not_active Ceased
- 2017-09-22 KR KR1020197011658A patent/KR20190076967A/ko not_active Ceased
- 2017-09-22 CN CN201780056790.7A patent/CN109715633B/zh not_active Expired - Fee Related
- 2017-09-22 CN CN201780056801.1A patent/CN109715155A/zh active Pending
- 2017-09-22 TW TW106132669A patent/TW201817713A/zh unknown
- 2017-09-22 EP EP17778369.3A patent/EP3515433A1/en not_active Withdrawn
- 2017-09-22 MA MA046280A patent/MA46280A/fr unknown
- 2017-09-22 BR BR112019004254A patent/BR112019004254A2/pt not_active IP Right Cessation
- 2017-09-22 KR KR1020197010873A patent/KR20190080864A/ko not_active Withdrawn
- 2017-09-22 AU AU2017330174A patent/AU2017330174A1/en not_active Abandoned
- 2017-09-22 SG SG11201901817SA patent/SG11201901817SA/en unknown
- 2017-09-22 SG SG11201901850XA patent/SG11201901850XA/en unknown
- 2017-09-22 MX MX2019003352A patent/MX384293B/es unknown
- 2017-09-22 US US16/335,529 patent/US11034695B2/en not_active Expired - Fee Related
- 2017-09-22 MA MA046273A patent/MA46273A/fr unknown
- 2017-09-22 JP JP2019515929A patent/JP2019529460A/ja active Pending
- 2017-09-22 MX MX2019003310A patent/MX381129B/es unknown
- 2017-09-22 JP JP2019515915A patent/JP2019529459A/ja not_active Ceased
- 2017-09-22 PE PE2019000690A patent/PE20190964A1/es unknown
- 2017-09-22 EP EP17787270.2A patent/EP3515917A1/en not_active Withdrawn
- 2017-09-22 TW TW106132670A patent/TWI746644B/zh not_active IP Right Cessation
- 2017-09-22 UA UAA201904171A patent/UA123071C2/uk unknown
- 2017-09-22 CA CA3037692A patent/CA3037692A1/en not_active Abandoned
- 2017-09-22 UA UAA201904180A patent/UA125479C2/uk unknown
-
2019
- 2019-03-03 IL IL265139A patent/IL265139B/en unknown
- 2019-03-03 IL IL265138A patent/IL265138B/en unknown
- 2019-03-14 CL CL2019000661A patent/CL2019000661A1/es unknown
- 2019-03-14 CL CL2019000662A patent/CL2019000662A1/es unknown
- 2019-03-15 PH PH12019500568A patent/PH12019500568A1/en unknown
- 2019-03-15 PH PH12019500569A patent/PH12019500569A1/en unknown
- 2019-03-18 CO CONC2019/0002523A patent/CO2019002523A2/es unknown
- 2019-03-18 CO CONC2019/0002517A patent/CO2019002517A2/es unknown
-
2021
- 2021-03-11 US US17/198,606 patent/US20220017523A1/en not_active Abandoned
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