JPWO2020039025A5 - - Google Patents
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- Publication number
- JPWO2020039025A5 JPWO2020039025A5 JP2021510100A JP2021510100A JPWO2020039025A5 JP WO2020039025 A5 JPWO2020039025 A5 JP WO2020039025A5 JP 2021510100 A JP2021510100 A JP 2021510100A JP 2021510100 A JP2021510100 A JP 2021510100A JP WO2020039025 A5 JPWO2020039025 A5 JP WO2020039025A5
- Authority
- JP
- Japan
- Prior art keywords
- oxy
- sulfonyl
- formula
- compound
- nitrophenyl
- 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
- -1 [(trifluoromethyl)sulfonyl]oxy Chemical group 0.000 claims 111
- 150000001875 compounds Chemical class 0.000 claims 46
- 238000000034 method Methods 0.000 claims 17
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 16
- 239000002904 solvent Substances 0.000 claims 15
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 9
- 229910052801 chlorine Inorganic materials 0.000 claims 9
- 239000000460 chlorine Substances 0.000 claims 9
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 8
- 229910052794 bromium Inorganic materials 0.000 claims 8
- 229910052740 iodine Inorganic materials 0.000 claims 8
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 8
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 8
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 7
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 7
- 239000007864 aqueous solution Substances 0.000 claims 7
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 5
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 claims 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- 239000008346 aqueous phase Substances 0.000 claims 3
- 239000000243 solution Substances 0.000 claims 3
- 239000011877 solvent mixture Substances 0.000 claims 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- PVJZBZSCGJAWNG-UHFFFAOYSA-N 2,4,6-trimethylbenzenesulfonyl chloride Chemical compound CC1=CC(C)=C(S(Cl)(=O)=O)C(C)=C1 PVJZBZSCGJAWNG-UHFFFAOYSA-N 0.000 claims 2
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims 2
- 229940011051 isopropyl acetate Drugs 0.000 claims 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 229910052763 palladium Inorganic materials 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- FWSFZQRVEWYSKU-LIXIDFRTSA-N (3R)-3-methyl-4-[4-(2-methylpyrazol-3-yl)-8-[2-(oxan-2-yl)pyrazol-3-yl]-1,7-naphthyridin-2-yl]morpholine Chemical compound C[C@@H]1COCCN1C1=CC(C2=CC=NN2C)=C2C=CN=C(C3=CC=NN3C3CCCCO3)C2=N1 FWSFZQRVEWYSKU-LIXIDFRTSA-N 0.000 claims 1
- DIOHEXPTUTVCNX-UHFFFAOYSA-N 1,1,1-trifluoro-n-phenyl-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)N(S(=O)(=O)C(F)(F)F)C1=CC=CC=C1 DIOHEXPTUTVCNX-UHFFFAOYSA-N 0.000 claims 1
- IRFCLLARAUQTNK-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl chloride Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)S(Cl)(=O)=O IRFCLLARAUQTNK-UHFFFAOYSA-N 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- ZZRFDLHBMBHJTI-UHFFFAOYSA-N 1-(oxan-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=NN1C1OCCCC1 ZZRFDLHBMBHJTI-UHFFFAOYSA-N 0.000 claims 1
- HLXOVAMYQUFLPE-UHFFFAOYSA-N 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole Chemical compound CN1N=CC=C1B1OC(C)(C)C(C)(C)O1 HLXOVAMYQUFLPE-UHFFFAOYSA-N 0.000 claims 1
- JAPYIBBSTJFDAK-UHFFFAOYSA-N 2,4,6-tri(propan-2-yl)benzenesulfonyl chloride Chemical compound CC(C)C1=CC(C(C)C)=C(S(Cl)(=O)=O)C(C(C)C)=C1 JAPYIBBSTJFDAK-UHFFFAOYSA-N 0.000 claims 1
- WPHUUIODWRNJLO-UHFFFAOYSA-N 2-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=CC=C1S(Cl)(=O)=O WPHUUIODWRNJLO-UHFFFAOYSA-N 0.000 claims 1
- KMMHZIBWCXYAAH-UHFFFAOYSA-N 4-bromobenzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=C(Br)C=C1 KMMHZIBWCXYAAH-UHFFFAOYSA-N 0.000 claims 1
- DTJVECUKADWGMO-UHFFFAOYSA-N 4-methoxybenzenesulfonyl chloride Chemical compound COC1=CC=C(S(Cl)(=O)=O)C=C1 DTJVECUKADWGMO-UHFFFAOYSA-N 0.000 claims 1
- JXRGUPLJCCDGKG-UHFFFAOYSA-N 4-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=C(S(Cl)(=O)=O)C=C1 JXRGUPLJCCDGKG-UHFFFAOYSA-N 0.000 claims 1
- CETRNHJIXGITKR-UHFFFAOYSA-N 4-propan-2-ylbenzenesulfonyl chloride Chemical compound CC(C)C1=CC=C(S(Cl)(=O)=O)C=C1 CETRNHJIXGITKR-UHFFFAOYSA-N 0.000 claims 1
- YEZADZMMVHWFIY-UHFFFAOYSA-N 4-tert-butylbenzenesulfonyl chloride Chemical compound CC(C)(C)C1=CC=C(S(Cl)(=O)=O)C=C1 YEZADZMMVHWFIY-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- XIBNHELYULXSME-MRVPVSSYSA-N C[C@@H]1COCCN1C1=CC(O)=C2C=CN=C(Cl)C2=N1 Chemical compound C[C@@H]1COCCN1C1=CC(O)=C2C=CN=C(Cl)C2=N1 XIBNHELYULXSME-MRVPVSSYSA-N 0.000 claims 1
- UQOYKSYVPXVSCW-MRVPVSSYSA-N [8-chloro-2-[(3R)-3-methylmorpholin-4-yl]-1,7-naphthyridin-4-yl] trifluoromethanesulfonate Chemical compound FC(S(=O)(=O)OC1=CC(=NC2=C(N=CC=C12)Cl)N1[C@@H](COCC1)C)(F)F UQOYKSYVPXVSCW-MRVPVSSYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 claims 1
- 230000002051 biphasic effect Effects 0.000 claims 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- LUYQYZLEHLTPBH-UHFFFAOYSA-N perfluorobutanesulfonyl fluoride Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)S(F)(=O)=O LUYQYZLEHLTPBH-UHFFFAOYSA-N 0.000 claims 1
- 239000012071 phase Substances 0.000 claims 1
- 239000002516 radical scavenger Substances 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP18190731 | 2018-08-24 | ||
| EP18190731.2 | 2018-08-24 | ||
| PCT/EP2019/072467 WO2020039025A1 (en) | 2018-08-24 | 2019-08-22 | Method for preparing 2-[(3r)-3-methylmorpholin-4-yl]-4-[1-methyl-1h-pyrazol-5-yl)-8-(1h-pyrazol-5-yl)-1,7-naphthyridine |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2021535122A JP2021535122A (ja) | 2021-12-16 |
| JPWO2020039025A5 true JPWO2020039025A5 (es) | 2022-08-29 |
| JP7422741B2 JP7422741B2 (ja) | 2024-01-26 |
Family
ID=63405064
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021510100A Active JP7422741B2 (ja) | 2018-08-24 | 2019-08-22 | ２－［（３ｒ）－３－メチルモルホリン－４－イル］－４－（１－メチル－１ｈ－ピラゾール－５－イル）－８－（１ｈ－ピラゾール－５－イル）－１，７－ナフチリジンを調製する方法 |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US20210253573A1 (es) |
| EP (1) | EP3841101B1 (es) |
| JP (1) | JP7422741B2 (es) |
| KR (1) | KR20210049845A (es) |
| CN (1) | CN112823158B (es) |
| AU (1) | AU2019324521A1 (es) |
| BR (1) | BR112021001309A2 (es) |
| CA (1) | CA3110394A1 (es) |
| CL (1) | CL2021000454A1 (es) |
| CO (1) | CO2021001892A2 (es) |
| DK (1) | DK3841101T3 (es) |
| ES (1) | ES2950825T3 (es) |
| FI (1) | FI3841101T3 (es) |
| HR (1) | HRP20230611T1 (es) |
| HU (1) | HUE062332T2 (es) |
| IL (1) | IL280878A (es) |
| JO (1) | JOP20210032A1 (es) |
| LT (1) | LT3841101T (es) |
| MX (1) | MX2021002132A (es) |
| PE (1) | PE20210862A1 (es) |
| PL (1) | PL3841101T3 (es) |
| PT (1) | PT3841101T (es) |
| RS (1) | RS64362B1 (es) |
| SG (1) | SG11202101011RA (es) |
| SI (1) | SI3841101T1 (es) |
| WO (1) | WO2020039025A1 (es) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI656121B (zh) | 2014-08-04 | 2019-04-11 | 德商拜耳製藥公司 | ２－（嗎啉－４－基）－１，７－萘啶 |
| CA3071760A1 (en) | 2017-08-04 | 2019-02-07 | Bayer Pharma Aktiengesellschaft | Combination of atr kinase inhibitors and pd-1/pd-l1 inhibitors |
| US11236070B2 (en) | 2019-05-16 | 2022-02-01 | Novartis Ag | Chemical process |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2645583A1 (en) * | 2006-03-20 | 2007-09-27 | F. Hoffman-La Roche Ag | Methods of inhibiting btk and syk protein kinases |
| JP2010529031A (ja) | 2007-05-29 | 2010-08-26 | グラクソスミスクライン・リミテッド・ライアビリティ・カンパニー | Ｐｉ３キナーゼ阻害剤としてのナフチリジン誘導体 |
| EA201100426A1 (ru) | 2008-09-02 | 2011-10-31 | Новартис Аг | Бициклические ингибиторы киназы |
| MX349366B (es) | 2011-05-19 | 2017-07-26 | Centro Nac De Investigaciones Oncologicas (Cnio) | Compuestos novedosos. |
| KR101366368B1 (ko) * | 2011-07-08 | 2014-02-21 | 주식회사 두산 | 신규 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자 |
| TWI656121B (zh) * | 2014-08-04 | 2019-04-11 | 德商拜耳製藥公司 | ２－（嗎啉－４－基）－１，７－萘啶 |
| WO2018153970A1 (en) * | 2017-02-24 | 2018-08-30 | Bayer Pharma Aktiengesellschaft | Solid forms of 2-[(3r)-3-methylmorpholin-4-yl]-4-(1-methyl-1h-pyrazol-5-yl)-8-(1h-pyrazol-5-yl)-1,7-naphthyridine |
-
2019
- 2019-08-22 BR BR112021001309-1A patent/BR112021001309A2/pt unknown
- 2019-08-22 EP EP19759528.3A patent/EP3841101B1/en active Active
- 2019-08-22 WO PCT/EP2019/072467 patent/WO2020039025A1/en unknown
- 2019-08-22 PT PT197595283T patent/PT3841101T/pt unknown
- 2019-08-22 JP JP2021510100A patent/JP7422741B2/ja active Active
- 2019-08-22 PE PE2021000226A patent/PE20210862A1/es unknown
- 2019-08-22 ES ES19759528T patent/ES2950825T3/es active Active
- 2019-08-22 AU AU2019324521A patent/AU2019324521A1/en active Pending
- 2019-08-22 PL PL19759528.3T patent/PL3841101T3/pl unknown
- 2019-08-22 HR HRP20230611TT patent/HRP20230611T1/hr unknown
- 2019-08-22 KR KR1020217008211A patent/KR20210049845A/ko not_active Application Discontinuation
- 2019-08-22 JO JOP/2021/0032A patent/JOP20210032A1/ar unknown
- 2019-08-22 DK DK19759528.3T patent/DK3841101T3/da active
- 2019-08-22 SG SG11202101011RA patent/SG11202101011RA/en unknown
- 2019-08-22 CA CA3110394A patent/CA3110394A1/en active Pending
- 2019-08-22 LT LTEPPCT/EP2019/072467T patent/LT3841101T/lt unknown
- 2019-08-22 MX MX2021002132A patent/MX2021002132A/es unknown
- 2019-08-22 CN CN201980055859.3A patent/CN112823158B/zh active Active
- 2019-08-22 SI SI201930551T patent/SI3841101T1/sl unknown
- 2019-08-22 US US17/271,141 patent/US20210253573A1/en active Pending
- 2019-08-22 HU HUE19759528A patent/HUE062332T2/hu unknown
- 2019-08-22 RS RS20230548A patent/RS64362B1/sr unknown
- 2019-08-22 FI FIEP19759528.3T patent/FI3841101T3/fi active
-
2021
- 2021-02-15 IL IL280878A patent/IL280878A/en unknown
- 2021-02-17 CO CONC2021/0001892A patent/CO2021001892A2/es unknown
- 2021-02-23 CL CL2021000454A patent/CL2021000454A1/es unknown
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