JP2019514903A5 - - Google Patents
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- Publication number
- JP2019514903A5 JP2019514903A5 JP2018555938A JP2018555938A JP2019514903A5 JP 2019514903 A5 JP2019514903 A5 JP 2019514903A5 JP 2018555938 A JP2018555938 A JP 2018555938A JP 2018555938 A JP2018555938 A JP 2018555938A JP 2019514903 A5 JP2019514903 A5 JP 2019514903A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- azabicyclo
- methyl
- pyrazol
- nonan
- 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 88
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 72
- -1 oct-8-yl Chemical group 0.000 claims description 63
- 150000001875 compounds Chemical class 0.000 claims description 61
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 24
- 125000004076 pyridyl group Chemical group 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 21
- 208000017189 Gastrointestinal inflammatory disease Diseases 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 18
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 18
- 241000124008 Mammalia Species 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 14
- 208000027866 inflammatory disease Diseases 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 12
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 12
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 10
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- PBIUUJCEMUAWJJ-UHFFFAOYSA-N azetidine-3-carbonitrile Chemical compound N#CC1CNC1 PBIUUJCEMUAWJJ-UHFFFAOYSA-N 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 8
- UCTUKXLCLYHJME-QBZDVNTPSA-N 1-[[(1R,5S)-3-[[4-[[5-(hydroxymethyl)pyrazolidin-3-yl]amino]-6-methoxypyrimidin-2-yl]-methylamino]-9-azabicyclo[3.3.1]nonan-9-yl]sulfonyl]azetidine-3-carbonitrile Chemical compound COc1cc(NC2CC(CO)NN2)nc(n1)N(C)C1C[C@@H]2CCC[C@H](C1)N2S(=O)(=O)N1CC(C1)C#N UCTUKXLCLYHJME-QBZDVNTPSA-N 0.000 claims description 7
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 6
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 6
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 6
- 201000008937 atopic dermatitis Diseases 0.000 claims description 6
- 125000002393 azetidinyl group Chemical group 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 229940124597 therapeutic agent Drugs 0.000 claims description 6
- FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 claims description 4
- ZMBLTLSKPTWFEZ-QBZDVNTPSA-N 2-methylpropyl (1R,5S)-3-[[4-[[5-(hydroxymethyl)pyrazolidin-3-yl]amino]-6-methoxypyrimidin-2-yl]-methylamino]-9-azabicyclo[3.3.1]nonane-9-carboxylate Chemical compound COc1cc(NC2CC(CO)NN2)nc(n1)N(C)C1C[C@@H]2CCC[C@H](C1)N2C(=O)OCC(C)C ZMBLTLSKPTWFEZ-QBZDVNTPSA-N 0.000 claims description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- GGRFGFBPDXMJFO-PVOWQQPYSA-N [5-[[6-methoxy-2-[[(1R,5S)-9-(2-methoxyethylsulfonyl)-9-azabicyclo[3.3.1]nonan-3-yl]-methylamino]pyrimidin-4-yl]amino]pyrazolidin-3-yl]methanol Chemical compound COCCS(=O)(=O)N1[C@H]2CCC[C@@H]1CC(C2)N(C)c1nc(NC2CC(CO)NN2)cc(OC)n1 GGRFGFBPDXMJFO-PVOWQQPYSA-N 0.000 claims description 4
- GTOQQHCRYJBYEX-PCQUJAHOSA-N [5-[[6-methoxy-2-[methyl-[(1R,5S)-9-methylsulfonyl-9-azabicyclo[3.3.1]nonan-3-yl]amino]pyrimidin-4-yl]amino]pyrazolidin-3-yl]methanol Chemical compound COc1cc(NC2CC(CO)NN2)nc(n1)N(C)C1C[C@@H]2CCC[C@H](C1)N2S(C)(=O)=O GTOQQHCRYJBYEX-PCQUJAHOSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000002757 morpholinyl group Chemical group 0.000 claims description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 3
- RLDWUPNOCFQQOB-WPSIBSQOSA-N 5-[[(1S,5R)-3-[[4-[[5-(hydroxymethyl)pyrazolidin-3-yl]amino]-6-methoxypyrimidin-2-yl]-methylamino]-9-azabicyclo[3.3.1]nonan-9-yl]methyl]pyridine-3-carbonitrile Chemical compound COc1cc(NC2CC(CO)NN2)nc(n1)N(C)C1C[C@@H]2CCC[C@H](C1)N2Cc1cncc(c1)C#N RLDWUPNOCFQQOB-WPSIBSQOSA-N 0.000 claims description 2
- KKKIEHCMACYQKK-XTFVGRHZSA-N 5-[[(1S,5R)-3-[[4-[[5-(hydroxymethyl)pyrazolidin-3-yl]amino]-6-methoxypyrimidin-2-yl]amino]-9-azabicyclo[3.3.1]nonan-9-yl]methyl]pyridine-2-carbonitrile Chemical compound COc1cc(NC2CC(CO)NN2)nc(NC2C[C@@H]3CCC[C@H](C2)N3Cc2ccc(nc2)C#N)n1 KKKIEHCMACYQKK-XTFVGRHZSA-N 0.000 claims description 2
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- AUQDITHEDVOTCU-UHFFFAOYSA-N cyclopropyl cyanide Chemical compound N#CC1CC1 AUQDITHEDVOTCU-UHFFFAOYSA-N 0.000 claims description 2
- 238000000113 differential scanning calorimetry Methods 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims description 2
- LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000006413 ring segment Chemical group 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 208000015943 Coeliac disease Diseases 0.000 claims 3
- 208000011231 Crohn disease Diseases 0.000 claims 3
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 1
- 0 *Nc1nc(Nc2n[n]c(CO)c2)cc(O*)n1 Chemical compound *Nc1nc(Nc2n[n]c(CO)c2)cc(O*)n1 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- BPVYRJYKOVEFOW-UHFFFAOYSA-N COC1=NC=NC(=C1)NC2=NNC(=C2)CO Chemical compound COC1=NC=NC(=C1)NC2=NNC(=C2)CO BPVYRJYKOVEFOW-UHFFFAOYSA-N 0.000 description 1
- 238000013160 medical therapy Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662328737P | 2016-04-28 | 2016-04-28 | |
| US62/328,737 | 2016-04-28 | ||
| PCT/US2017/029796 WO2017189822A1 (en) | 2016-04-28 | 2017-04-27 | Pyrimidine compounds as jak kinase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019514903A JP2019514903A (ja) | 2019-06-06 |
| JP2019514903A5 true JP2019514903A5 (enExample) | 2020-04-23 |
| JP6881879B2 JP6881879B2 (ja) | 2021-06-02 |
Family
ID=58672793
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018555938A Active JP6881879B2 (ja) | 2016-04-28 | 2017-04-27 | Ｊａｋキナーゼ阻害剤としてのピリミジン化合物 |
Country Status (20)
| Country | Link |
|---|---|
| US (3) | US10028960B2 (enExample) |
| EP (1) | EP3433253B1 (enExample) |
| JP (1) | JP6881879B2 (enExample) |
| KR (1) | KR102244257B1 (enExample) |
| CN (1) | CN109071529B (enExample) |
| AU (1) | AU2017258186B2 (enExample) |
| BR (1) | BR112018072168A2 (enExample) |
| CA (1) | CA3020506A1 (enExample) |
| CL (1) | CL2018003060A1 (enExample) |
| CO (1) | CO2018011408A2 (enExample) |
| DK (1) | DK3433253T3 (enExample) |
| EA (1) | EA035226B1 (enExample) |
| ES (1) | ES2779880T3 (enExample) |
| IL (1) | IL262386B (enExample) |
| MX (1) | MX377180B (enExample) |
| PT (1) | PT3433253T (enExample) |
| SG (1) | SG11201809342YA (enExample) |
| TW (1) | TWI726094B (enExample) |
| WO (1) | WO2017189822A1 (enExample) |
| ZA (1) | ZA201807179B (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20180011272A (ko) | 2015-05-28 | 2018-01-31 | 세라밴스 바이오파마 알앤디 아이피, 엘엘씨 | Jak 키나제 저해제로서 나프티리딘 화합물 |
| DK3712152T3 (da) | 2015-11-03 | 2021-03-22 | Topivert Pharma Ltd | 4,5,6,7-tetrahydro-1h-imidazo[4,5-c]pyridin og 1,4,5,6,7,8-hexahydroimidazo[4,5-d]azepinderivater som janus kinase-inhibitorer |
| EP3371185B1 (en) | 2015-11-03 | 2020-09-30 | Topivert Pharma Limited | 4,5,6,7-tetrahydro-1h-imidazo[4,5-c]pyridine and 1,4,5,6,7,8-hexahydroimidazo[4,5-d]azepine derivatives as janus kinase inhibitors |
| CA3020506A1 (en) | 2016-04-28 | 2017-11-02 | Theravance Biopharma R&D Ip, Llc | Pyrimidine compounds as jak kinase inhibitors |
| GEP20227344B (en) | 2017-10-27 | 2022-01-25 | Theravance Biopharma R&D Ip Llc | Pyrimidine compound as jak kinase inhibitor |
| US12171764B2 (en) | 2018-06-20 | 2024-12-24 | Biora Therapeutics, Inc. | Treatment of a disease of the gastrointestinal tract with a JAK or other kinase inhibitor |
| CN111601804B (zh) * | 2018-11-27 | 2024-06-04 | 江苏豪森药业集团有限公司 | 含氮杂芳类衍生物调节剂、其制备方法和应用 |
| CN115925705B (zh) * | 2018-11-30 | 2024-12-31 | 江苏豪森药业集团有限公司 | 杂芳类衍生物调节剂、其制备方法和应用 |
| TW202106681A (zh) * | 2019-04-24 | 2021-02-16 | 美商施萬生物製藥研發Ｉｐ有限責任公司 | 用於治療皮膚疾病之嘧啶jak抑制劑 |
| TW202106682A (zh) | 2019-04-24 | 2021-02-16 | 美商施萬生物製藥研發Ｉｐ有限責任公司 | 作為jak激酶抑制劑之酯類及碳酸酯類嘧啶化合物 |
| EP4149462A4 (en) * | 2020-05-14 | 2024-04-24 | Theravance Biopharma R&D IP, LLC | Administration of gut-selective jak3 inhibitor |
| UY39454A (es) * | 2020-10-09 | 2022-04-29 | Janssen Biotech Inc | Procesos para preparar un inhibidor de pan-jak y compuestos intermedios relacionados |
| CN116390922B (zh) * | 2020-10-21 | 2025-07-18 | 珠海联邦制药股份有限公司 | 硒杂环类化合物及其应用 |
| WO2023011359A1 (zh) * | 2021-08-05 | 2023-02-09 | 南京明德新药研发有限公司 | 桥环类化合物及其应用 |
| CN113883920B (zh) * | 2021-10-25 | 2024-01-23 | 安徽华铂再生资源科技有限公司 | 一种降低空分装置空冷塔出口温度的方法 |
| WO2023202706A1 (zh) * | 2022-04-21 | 2023-10-26 | 南京明德新药研发有限公司 | 硒杂环类化合物的盐型和晶型及其应用 |
| WO2025040148A1 (zh) * | 2023-08-22 | 2025-02-27 | 北京普祺医药科技股份有限公司 | 一种用于jak抑制剂的外用凝胶及其用途 |
| TW202515852A (zh) * | 2023-09-15 | 2025-04-16 | 美商莫菲克醫療股份有限公司 | 抑制人類整合素α４β７ |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6660731B2 (en) | 2000-09-15 | 2003-12-09 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| CA2432799C (en) | 2000-12-21 | 2008-08-19 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| WO2006074057A2 (en) * | 2004-12-30 | 2006-07-13 | Exelixis, Inc. | Pyrimidine derivatives as kinase modulators and method of use |
| CN101360740A (zh) | 2005-11-16 | 2009-02-04 | 沃泰克斯药物股份有限公司 | 可用作激酶抑制剂的氨基嘧啶 |
| UY30444A1 (es) | 2006-06-30 | 2008-01-31 | Astrazeneca Ab | Derivados de pirimidina, procesos para su preparacinn, composiciones farmaccuticos y usos de los mismos. |
| EP2043651A2 (en) | 2006-07-05 | 2009-04-08 | Exelixis, Inc. | Methods of using igf1r and abl kinase modulators |
| RU2014129740A (ru) | 2011-12-22 | 2016-02-10 | Ф.Хоффманн-Ля Рош Аг | Производные 2,4-диаминопиримидина в качестве ингибиторов серин/треонин киназы |
| WO2015094803A1 (en) | 2013-12-16 | 2015-06-25 | Calitor Sciences, Llc | Substituted heteroaryl compounds and methods of use |
| NO2721710T3 (enExample) * | 2014-08-21 | 2018-03-31 | ||
| KR20180011272A (ko) | 2015-05-28 | 2018-01-31 | 세라밴스 바이오파마 알앤디 아이피, 엘엘씨 | Jak 키나제 저해제로서 나프티리딘 화합물 |
| CA3020506A1 (en) * | 2016-04-28 | 2017-11-02 | Theravance Biopharma R&D Ip, Llc | Pyrimidine compounds as jak kinase inhibitors |
-
2017
- 2017-04-27 CA CA3020506A patent/CA3020506A1/en not_active Abandoned
- 2017-04-27 EA EA201892436A patent/EA035226B1/ru unknown
- 2017-04-27 TW TW106114033A patent/TWI726094B/zh not_active IP Right Cessation
- 2017-04-27 SG SG11201809342YA patent/SG11201809342YA/en unknown
- 2017-04-27 JP JP2018555938A patent/JP6881879B2/ja active Active
- 2017-04-27 ES ES17722324T patent/ES2779880T3/es active Active
- 2017-04-27 EP EP17722324.5A patent/EP3433253B1/en active Active
- 2017-04-27 US US15/498,803 patent/US10028960B2/en not_active Expired - Fee Related
- 2017-04-27 WO PCT/US2017/029796 patent/WO2017189822A1/en not_active Ceased
- 2017-04-27 AU AU2017258186A patent/AU2017258186B2/en not_active Ceased
- 2017-04-27 MX MX2018013191A patent/MX377180B/es active IP Right Grant
- 2017-04-27 KR KR1020187034319A patent/KR102244257B1/ko not_active Expired - Fee Related
- 2017-04-27 DK DK17722324.5T patent/DK3433253T3/da active
- 2017-04-27 BR BR112018072168-9A patent/BR112018072168A2/pt not_active Application Discontinuation
- 2017-04-27 PT PT177223245T patent/PT3433253T/pt unknown
- 2017-04-27 CN CN201780026437.4A patent/CN109071529B/zh not_active Expired - Fee Related
-
2018
- 2018-06-21 US US16/014,233 patent/US10485803B2/en active Active
- 2018-10-15 IL IL262386A patent/IL262386B/en unknown
- 2018-10-25 CO CONC2018/0011408A patent/CO2018011408A2/es unknown
- 2018-10-26 ZA ZA2018/07179A patent/ZA201807179B/en unknown
- 2018-10-26 CL CL2018003060A patent/CL2018003060A1/es unknown
-
2019
- 2019-10-18 US US16/656,927 patent/US11110095B2/en active Active
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