JP2017524742A5 - - Google Patents
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- Publication number
- JP2017524742A5 JP2017524742A5 JP2017528754A JP2017528754A JP2017524742A5 JP 2017524742 A5 JP2017524742 A5 JP 2017524742A5 JP 2017528754 A JP2017528754 A JP 2017528754A JP 2017528754 A JP2017528754 A JP 2017528754A JP 2017524742 A5 JP2017524742 A5 JP 2017524742A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- acid
- alkyl
- mixture
- 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
- 238000000034 method Methods 0.000 claims 19
- 150000001875 compounds Chemical class 0.000 claims 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 4
- 239000003054 catalyst Substances 0.000 claims 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 238000002360 preparation method Methods 0.000 claims 3
- 239000011541 reaction mixture Substances 0.000 claims 3
- 229940126062 Compound A Drugs 0.000 claims 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical group CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 239000012454 non-polar solvent Substances 0.000 claims 2
- 238000001556 precipitation Methods 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- CMIBUZBMZCBCAT-HZPDHXFCSA-N (2r,3r)-2,3-bis[(4-methylbenzoyl)oxy]butanedioic acid Chemical compound C1=CC(C)=CC=C1C(=O)O[C@@H](C(O)=O)[C@H](C(O)=O)OC(=O)C1=CC=C(C)C=C1 CMIBUZBMZCBCAT-HZPDHXFCSA-N 0.000 claims 1
- ODGIMMLDVSWADK-UHFFFAOYSA-N 4-trifluoromethylaniline Chemical compound NC1=CC=C(C(F)(F)F)C=C1 ODGIMMLDVSWADK-UHFFFAOYSA-N 0.000 claims 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 claims 1
- 239000007848 Bronsted acid Substances 0.000 claims 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical group OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
- 239000002841 Lewis acid Substances 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 150000007517 lewis acids Chemical class 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical group CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
- 238000010792 warming Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL2014050556 | 2014-08-12 | ||
| NLPCT/NL2014/050556 | 2014-08-12 | ||
| PCT/NL2015/050555 WO2016024858A1 (en) | 2014-08-12 | 2015-07-29 | Process for preparing synthetic intermediates for preparing tetrahydroquinoline derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017524742A JP2017524742A (ja) | 2017-08-31 |
| JP2017524742A5 true JP2017524742A5 (OSRAM) | 2018-09-06 |
| JP6670310B2 JP6670310B2 (ja) | 2020-03-18 |
Family
ID=51429345
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017528754A Active JP6670310B2 (ja) | 2014-08-12 | 2015-07-29 | テトラヒドロキノリン誘導体の調製のための合成中間体の調製方法 |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US10112904B2 (OSRAM) |
| EP (2) | EP3180314B1 (OSRAM) |
| JP (1) | JP6670310B2 (OSRAM) |
| KR (1) | KR102572626B1 (OSRAM) |
| CN (1) | CN107108558B (OSRAM) |
| AR (1) | AR101509A1 (OSRAM) |
| AU (1) | AU2015302407B2 (OSRAM) |
| BR (1) | BR112017002873B1 (OSRAM) |
| CA (1) | CA2958040C (OSRAM) |
| CL (1) | CL2017000367A1 (OSRAM) |
| DK (1) | DK3180314T3 (OSRAM) |
| EA (1) | EA034357B1 (OSRAM) |
| ES (1) | ES2926775T3 (OSRAM) |
| HR (1) | HRP20221061T1 (OSRAM) |
| HU (1) | HUE059947T2 (OSRAM) |
| IL (1) | IL250525B (OSRAM) |
| LT (1) | LT3180314T (OSRAM) |
| MA (1) | MA40378B1 (OSRAM) |
| MX (1) | MX367908B (OSRAM) |
| PL (1) | PL3180314T3 (OSRAM) |
| PT (1) | PT3180314T (OSRAM) |
| RS (1) | RS63575B1 (OSRAM) |
| SG (1) | SG11201701077XA (OSRAM) |
| SI (1) | SI3180314T1 (OSRAM) |
| SM (1) | SMT202200385T1 (OSRAM) |
| TW (1) | TWI691490B (OSRAM) |
| WO (1) | WO2016024858A1 (OSRAM) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUE067276T2 (hu) | 2021-03-05 | 2024-10-28 | Newamsterdam Pharma B V | Obicetrapib demenciák kezelésére |
| JP2024527023A (ja) | 2021-07-26 | 2024-07-19 | ニューアムステルダム・ファルマ・ベー・フェー | Ｈｉｓ低応答者の治療 |
| AU2022425078A1 (en) | 2021-12-30 | 2024-08-08 | Newamsterdam Pharma B.V. | Obicetrapib and sglt2 inhibitor combination |
| EP4551567A1 (en) | 2022-07-05 | 2025-05-14 | NewAmsterdam Pharma B.V. | Salts of obicetrapib and processes for their manufacture and intermediates thereof |
| WO2024042061A1 (en) | 2022-08-22 | 2024-02-29 | Newamsterdam Pharma B.V. | Obicetrapib and ezetimibe combination treatment and fixed dose pharmaceutical compositions |
| EP4661865A1 (en) | 2023-02-07 | 2025-12-17 | NewAmsterdam Pharma B.V. | Obicetrapib and ezetimibe combination treatment and fixed dose pharmaceutical compositions |
| WO2025059594A1 (en) | 2023-09-15 | 2025-03-20 | Newamsterdam Pharma B.V. | METHODS FOR TREATING HETEROZYGOUS FAMILIAL HYPERCHOLESTEROLEMIA (HeFH) |
| WO2025093129A1 (en) | 2023-11-01 | 2025-05-08 | Newamsterdam Pharma B.V. | Treatment and prevention of age-related macular degeneration using a cetp inhibitor |
| WO2025093436A1 (en) | 2023-11-01 | 2025-05-08 | Newamsterdam Pharma B.V. | Treatment and prevention of age-related macular degeneration using a cetp inhibitor |
| WO2025146262A1 (en) | 2024-01-03 | 2025-07-10 | Newamsterdam Pharma B.V. | Obicetrapib for use in the treatment of hemoglobinopathies |
| WO2025146415A1 (en) | 2024-01-03 | 2025-07-10 | Newamsterdam Pharma B.V. | Improvement in atherosclerotic plaque characteristics with obicetrapib |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6197786B1 (en) * | 1998-09-17 | 2001-03-06 | Pfizer Inc | 4-Carboxyamino-2-substituted-1,2,3,4-tetrahydroquinolines |
| BR0209238A (pt) * | 2001-04-30 | 2004-06-15 | Pfizer Prod Inc | Compostos úteis como intermediários |
| UA90269C2 (ru) * | 2004-04-02 | 2010-04-26 | Мицубиси Танабе Фарма Корпорейшн | Тетрагидрохинолиновые производные и способ их получения |
| TW200808731A (en) * | 2006-03-30 | 2008-02-16 | Tanabe Seiyaku Co | A process for preparing tetrahydroquinoline derivatives |
| CN101466679A (zh) * | 2006-03-30 | 2009-06-24 | 田边三菱制药株式会社 | 制备四氢喹啉衍生物的方法 |
-
2015
- 2015-07-29 HR HRP20221061TT patent/HRP20221061T1/hr unknown
- 2015-07-29 CA CA2958040A patent/CA2958040C/en active Active
- 2015-07-29 US US15/503,686 patent/US10112904B2/en active Active
- 2015-07-29 LT LTEPPCT/NL2015/050555T patent/LT3180314T/lt unknown
- 2015-07-29 SG SG11201701077XA patent/SG11201701077XA/en unknown
- 2015-07-29 BR BR112017002873-5A patent/BR112017002873B1/pt active IP Right Grant
- 2015-07-29 JP JP2017528754A patent/JP6670310B2/ja active Active
- 2015-07-29 EA EA201790364A patent/EA034357B1/ru active IP Right Revival
- 2015-07-29 RS RS20220810A patent/RS63575B1/sr unknown
- 2015-07-29 KR KR1020177006422A patent/KR102572626B1/ko active Active
- 2015-07-29 DK DK15767345.0T patent/DK3180314T3/da active
- 2015-07-29 ES ES15767345T patent/ES2926775T3/es active Active
- 2015-07-29 PT PT157673450T patent/PT3180314T/pt unknown
- 2015-07-29 SM SM20220385T patent/SMT202200385T1/it unknown
- 2015-07-29 SI SI201531874T patent/SI3180314T1/sl unknown
- 2015-07-29 EP EP15767345.0A patent/EP3180314B1/en active Active
- 2015-07-29 PL PL15767345.0T patent/PL3180314T3/pl unknown
- 2015-07-29 EP EP22179712.9A patent/EP4083022A1/en active Pending
- 2015-07-29 MA MA40378A patent/MA40378B1/fr unknown
- 2015-07-29 WO PCT/NL2015/050555 patent/WO2016024858A1/en not_active Ceased
- 2015-07-29 CN CN201580046606.1A patent/CN107108558B/zh active Active
- 2015-07-29 AU AU2015302407A patent/AU2015302407B2/en active Active
- 2015-07-29 MX MX2017001930A patent/MX367908B/es active IP Right Grant
- 2015-07-29 HU HUE15767345A patent/HUE059947T2/hu unknown
- 2015-08-10 TW TW104125888A patent/TWI691490B/zh active
- 2015-08-11 AR ARP150102597A patent/AR101509A1/es active IP Right Grant
-
2017
- 2017-02-09 IL IL250525A patent/IL250525B/en active IP Right Grant
- 2017-02-10 CL CL2017000367A patent/CL2017000367A1/es unknown
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