JP2023089012A5 - - Google Patents
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- JP2023089012A5 JP2023089012A5 JP2023048083A JP2023048083A JP2023089012A5 JP 2023089012 A5 JP2023089012 A5 JP 2023089012A5 JP 2023048083 A JP2023048083 A JP 2023048083A JP 2023048083 A JP2023048083 A JP 2023048083A JP 2023089012 A5 JP2023089012 A5 JP 2023089012A5
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- Prior art keywords
- compound
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- pharmaceutical composition
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims 22
- 150000003839 salts Chemical class 0.000 claims 7
- -1 besylates Chemical class 0.000 claims 6
- 206010068715 Fibrodysplasia ossificans progressiva Diseases 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 102100034111 Activin receptor type-1 Human genes 0.000 claims 4
- 101000799140 Homo sapiens Activin receptor type-1 Proteins 0.000 claims 4
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 238000000634 powder X-ray diffraction Methods 0.000 claims 4
- 208000034970 Heterotopic Ossification Diseases 0.000 claims 3
- 239000002253 acid Chemical class 0.000 claims 3
- 230000007941 heterotopic ossification Effects 0.000 claims 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 3
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 2
- 229930195712 glutamate Natural products 0.000 claims 2
- 229940049906 glutamate Drugs 0.000 claims 2
- 230000005764 inhibitory process Effects 0.000 claims 2
- 235000005152 nicotinamide Nutrition 0.000 claims 2
- 239000011570 nicotinamide Substances 0.000 claims 2
- 229960003966 nicotinamide Drugs 0.000 claims 2
- 108020003175 receptors Proteins 0.000 claims 2
- 102000005962 receptors Human genes 0.000 claims 2
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 claims 1
- DCYGAPKNVCQNOE-UHFFFAOYSA-N 2,2,2-triphenylacetic acid Chemical class C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)O)C1=CC=CC=C1 DCYGAPKNVCQNOE-UHFFFAOYSA-N 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 claims 1
- AEMOLEFTQBMNLQ-AQKNRBDQSA-N D-glucopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-AQKNRBDQSA-N 0.000 claims 1
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- QIAFMBKCNZACKA-UHFFFAOYSA-N N-benzoylglycine Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1 QIAFMBKCNZACKA-UHFFFAOYSA-N 0.000 claims 1
- 229910002651 NO3 Inorganic materials 0.000 claims 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 1
- DFPAKSUCGFBDDF-ZQBYOMGUSA-N [14c]-nicotinamide Chemical compound N[14C](=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-ZQBYOMGUSA-N 0.000 claims 1
- 159000000021 acetate salts Chemical class 0.000 claims 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical class OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims 1
- 150000008064 anhydrides Chemical group 0.000 claims 1
- 125000003289 ascorbyl group Chemical class [H]O[C@@]([H])(C([H])([H])O*)[C@@]1([H])OC(=O)C(O*)=C1O* 0.000 claims 1
- CKLJMWTZIZZHCS-REOHCLBHSA-L aspartate group Chemical class N[C@@H](CC(=O)[O-])C(=O)[O-] CKLJMWTZIZZHCS-REOHCLBHSA-L 0.000 claims 1
- JPNZKPRONVOMLL-UHFFFAOYSA-N azane;octadecanoic acid Chemical class [NH4+].CCCCCCCCCCCCCCCCCC([O-])=O JPNZKPRONVOMLL-UHFFFAOYSA-N 0.000 claims 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-M bisulphate group Chemical group S([O-])(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims 1
- 150000003842 bromide salts Chemical class 0.000 claims 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical class C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 claims 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims 1
- 150000001805 chlorine compounds Chemical class 0.000 claims 1
- 125000005534 decanoate group Chemical class 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 claims 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 claims 1
- 229940043264 dodecyl sulfate Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- AFAXGSQYZLGZPG-UHFFFAOYSA-L ethane-1,2-disulfonate Chemical compound [O-]S(=O)(=O)CCS([O-])(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-L 0.000 claims 1
- 229940050410 gluconate Drugs 0.000 claims 1
- 229940097042 glucuronate Drugs 0.000 claims 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 claims 1
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 claims 1
- 229940001447 lactate Drugs 0.000 claims 1
- 229940099584 lactobionate Drugs 0.000 claims 1
- JYTUSYBCFIZPBE-AMTLMPIISA-N lactobionic acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O JYTUSYBCFIZPBE-AMTLMPIISA-N 0.000 claims 1
- 229940049920 malate Drugs 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 claims 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- 150000004682 monohydrates Chemical class 0.000 claims 1
- 235000001968 nicotinic acid Nutrition 0.000 claims 1
- 239000011664 nicotinic acid Substances 0.000 claims 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-M octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC([O-])=O QIQXTHQIDYTFRH-UHFFFAOYSA-M 0.000 claims 1
- 229940049964 oleate Drugs 0.000 claims 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims 1
- XENHFSZRMFXQBS-UHFFFAOYSA-N phosphoric acid;pyridine-3-carboxamide Chemical compound OP(O)(O)=O.NC(=O)C1=CC=CN=C1 XENHFSZRMFXQBS-UHFFFAOYSA-N 0.000 claims 1
- MOODSJOROWROTO-UHFFFAOYSA-N salicylsulfuric acid Chemical class OC(=O)C1=CC=CC=C1OS(O)(=O)=O MOODSJOROWROTO-UHFFFAOYSA-N 0.000 claims 1
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical class OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims 1
- 150000003890 succinate salts Chemical class 0.000 claims 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims 1
- 150000003892 tartrate salts Chemical class 0.000 claims 1
- 125000005490 tosylate group Chemical group 0.000 claims 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
- 150000004684 trihydrates Chemical class 0.000 claims 1
- 229950000339 xinafoate Drugs 0.000 claims 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2024193634A JP7834830B2 (ja) | 2016-07-20 | 2024-11-05 | アミノピリジン誘導体およびそれらの選択的ａｌｋ－２阻害剤としての使用 |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662364620P | 2016-07-20 | 2016-07-20 | |
| US62/364,620 | 2016-07-20 | ||
| PCT/CN2017/093385 WO2018014829A1 (en) | 2016-07-20 | 2017-07-18 | Aminopyridine derivatives and their use as selective alk-2 inhibitors |
| JP2019502675A JP7030776B2 (ja) | 2016-07-20 | 2017-07-18 | アミノピリジン誘導体およびそれらの選択的ａｌｋ－２阻害剤としての使用 |
| JP2022025894A JP7253086B2 (ja) | 2016-07-20 | 2022-02-22 | アミノピリジン誘導体およびそれらの選択的ａｌｋ－２阻害剤としての使用 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022025894A Division JP7253086B2 (ja) | 2016-07-20 | 2022-02-22 | アミノピリジン誘導体およびそれらの選択的ａｌｋ－２阻害剤としての使用 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2024193634A Division JP7834830B2 (ja) | 2016-07-20 | 2024-11-05 | アミノピリジン誘導体およびそれらの選択的ａｌｋ－２阻害剤としての使用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2023089012A JP2023089012A (ja) | 2023-06-27 |
| JP2023089012A5 true JP2023089012A5 (https=) | 2023-11-24 |
| JP7584553B2 JP7584553B2 (ja) | 2024-11-15 |
Family
ID=60991950
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019502675A Active JP7030776B2 (ja) | 2016-07-20 | 2017-07-18 | アミノピリジン誘導体およびそれらの選択的ａｌｋ－２阻害剤としての使用 |
| JP2022025894A Active JP7253086B2 (ja) | 2016-07-20 | 2022-02-22 | アミノピリジン誘導体およびそれらの選択的ａｌｋ－２阻害剤としての使用 |
| JP2023048083A Active JP7584553B2 (ja) | 2016-07-20 | 2023-03-24 | アミノピリジン誘導体およびそれらの選択的ａｌｋ－２阻害剤としての使用 |
| JP2024193634A Active JP7834830B2 (ja) | 2016-07-20 | 2024-11-05 | アミノピリジン誘導体およびそれらの選択的ａｌｋ－２阻害剤としての使用 |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019502675A Active JP7030776B2 (ja) | 2016-07-20 | 2017-07-18 | アミノピリジン誘導体およびそれらの選択的ａｌｋ－２阻害剤としての使用 |
| JP2022025894A Active JP7253086B2 (ja) | 2016-07-20 | 2022-02-22 | アミノピリジン誘導体およびそれらの選択的ａｌｋ－２阻害剤としての使用 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2024193634A Active JP7834830B2 (ja) | 2016-07-20 | 2024-11-05 | アミノピリジン誘導体およびそれらの選択的ａｌｋ－２阻害剤としての使用 |
Country Status (25)
| Country | Link |
|---|---|
| US (3) | US10710980B2 (https=) |
| EP (3) | EP3487851B1 (https=) |
| JP (4) | JP7030776B2 (https=) |
| KR (7) | KR20240155367A (https=) |
| CN (2) | CN109641871B (https=) |
| AR (1) | AR109108A1 (https=) |
| AU (5) | AU2017298187B2 (https=) |
| CY (1) | CY1124967T1 (https=) |
| DK (2) | DK3487851T3 (https=) |
| EA (2) | EA037520B1 (https=) |
| ES (2) | ES2984746T3 (https=) |
| FI (1) | FI3971177T3 (https=) |
| HR (2) | HRP20241015T1 (https=) |
| HU (2) | HUE067992T2 (https=) |
| LT (2) | LT3487851T (https=) |
| MX (2) | MX388518B (https=) |
| PL (2) | PL3971177T3 (https=) |
| PT (2) | PT3971177T (https=) |
| RS (2) | RS66041B1 (https=) |
| RU (1) | RU2747318C2 (https=) |
| SI (2) | SI3487851T1 (https=) |
| SM (2) | SMT202100723T1 (https=) |
| TW (5) | TWI851226B (https=) |
| UY (1) | UY37331A (https=) |
| WO (1) | WO2018014829A1 (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10710980B2 (en) * | 2016-07-20 | 2020-07-14 | Novartis Ag | Aminopyridine derivatives and their use as selective ALK-2 inhibitors |
| CN115038443A (zh) | 2019-11-22 | 2022-09-09 | 因西特公司 | 包含alk2抑制剂和jak2抑制剂的组合疗法 |
| CN111170893B (zh) * | 2020-01-19 | 2022-04-26 | 郑州依米花手性药物研究有限公司 | Lefamulin的中间体化合物及其在Lefamulin制备中的应用 |
| JP2023530316A (ja) | 2020-06-16 | 2023-07-14 | インサイト・コーポレイション | 貧血の治療のためのａｌｋ２阻害剤 |
| KR102913358B1 (ko) * | 2020-10-29 | 2026-01-14 | 주식회사 엘지화학 | 중수소화 화합물의 분석방법, 소자 제조용 중수소화 화합물의 선별방법 및 전자 소자의 제조방법 |
| US12115154B2 (en) | 2020-12-16 | 2024-10-15 | Srx Cardio, Llc | Compounds for the modulation of proprotein convertase subtilisin/kexin type 9 (PCSK9) |
| CN116478145B (zh) * | 2022-04-13 | 2024-02-02 | 杭州邦顺制药有限公司 | Alk2激酶抑制剂 |
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