JPWO2020010068A5 - - Google Patents
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- JPWO2020010068A5 JPWO2020010068A5 JP2020572517A JP2020572517A JPWO2020010068A5 JP WO2020010068 A5 JPWO2020010068 A5 JP WO2020010068A5 JP 2020572517 A JP2020572517 A JP 2020572517A JP 2020572517 A JP2020572517 A JP 2020572517A JP WO2020010068 A5 JPWO2020010068 A5 JP WO2020010068A5
- Authority
- JP
- Japan
- Prior art keywords
- crystalline salt
- pharmaceutical composition
- salt according
- subject
- diffraction pattern
- 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.)
- Pending
Links
- 150000003839 salts Chemical class 0.000 claims 37
- 239000008194 pharmaceutical composition Substances 0.000 claims 25
- 238000000634 powder X-ray diffraction Methods 0.000 claims 8
- 229940126062 Compound A Drugs 0.000 claims 4
- 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 4
- 206010045261 Type IIa hyperlipidaemia Diseases 0.000 claims 4
- 235000001014 amino acid Nutrition 0.000 claims 4
- 150000001413 amino acids Chemical group 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 229940079593 drug Drugs 0.000 claims 4
- 208000010706 fatty liver disease Diseases 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 208000000563 Hyperlipoproteinemia Type II Diseases 0.000 claims 3
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims 3
- 102100024640 Low-density lipoprotein receptor Human genes 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 201000001386 familial hypercholesterolemia Diseases 0.000 claims 3
- 239000012453 solvate Substances 0.000 claims 3
- 238000006467 substitution reaction Methods 0.000 claims 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims 2
- 239000004475 Arginine Substances 0.000 claims 2
- 208000032928 Dyslipidaemia Diseases 0.000 claims 2
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims 2
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 claims 2
- 239000004473 Threonine Substances 0.000 claims 2
- 102100033451 Thyroid hormone receptor beta Human genes 0.000 claims 2
- 235000004279 alanine Nutrition 0.000 claims 2
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims 2
- 235000009697 arginine Nutrition 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 229960002885 histidine Drugs 0.000 claims 2
- 230000035772 mutation Effects 0.000 claims 2
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims 2
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims 2
- -1 3,5-dichloro-4-((5-isopropyl-6-oxo-1,6-dihydropyridazine-3-yl) oxy) phenyl Chemical group 0.000 claims 1
- 206010003210 Arteriosclerosis Diseases 0.000 claims 1
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 1
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 1
- 208000020084 Bone disease Diseases 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 206010011878 Deafness Diseases 0.000 claims 1
- 206010012426 Dermal cyst Diseases 0.000 claims 1
- 208000004930 Fatty Liver Diseases 0.000 claims 1
- 206010019708 Hepatic steatosis Diseases 0.000 claims 1
- 208000035150 Hypercholesterolemia Diseases 0.000 claims 1
- 208000031226 Hyperlipidaemia Diseases 0.000 claims 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 claims 1
- 229930064664 L-arginine Natural products 0.000 claims 1
- 235000014852 L-arginine Nutrition 0.000 claims 1
- 208000036626 Mental retardation Diseases 0.000 claims 1
- LJMFFFZEUKITIM-UHFFFAOYSA-N N#CC1=CNCNN1 Chemical compound N#CC1=CNCNN1 LJMFFFZEUKITIM-UHFFFAOYSA-N 0.000 claims 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 208000001871 Tachycardia Diseases 0.000 claims 1
- 208000024770 Thyroid neoplasm Diseases 0.000 claims 1
- AUYYCJSJGJYCDS-LBPRGKRZSA-N Thyrolar Chemical class IC1=CC(C[C@H](N)C(O)=O)=CC(I)=C1OC1=CC=C(O)C(I)=C1 AUYYCJSJGJYCDS-LBPRGKRZSA-N 0.000 claims 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims 1
- 230000005856 abnormality Effects 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 150000001483 arginine derivatives Chemical class 0.000 claims 1
- 208000011775 arteriosclerosis disease Diseases 0.000 claims 1
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 1
- 210000000988 bone and bone Anatomy 0.000 claims 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 claims 1
- 230000003111 delayed effect Effects 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 claims 1
- 230000010370 hearing loss Effects 0.000 claims 1
- 231100000888 hearing loss Toxicity 0.000 claims 1
- 208000016354 hearing loss disease Diseases 0.000 claims 1
- 208000006454 hepatitis Diseases 0.000 claims 1
- 231100000283 hepatitis Toxicity 0.000 claims 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims 1
- 208000013403 hyperactivity Diseases 0.000 claims 1
- 208000003532 hypothyroidism Diseases 0.000 claims 1
- 230000002989 hypothyroidism Effects 0.000 claims 1
- 150000002632 lipids Chemical class 0.000 claims 1
- 230000000926 neurological effect Effects 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 208000020016 psychiatric disease Diseases 0.000 claims 1
- 230000001568 sexual effect Effects 0.000 claims 1
- 231100000240 steatosis hepatitis Toxicity 0.000 claims 1
- WPLOVIFNBMNBPD-ATHMIXSHSA-N subtilin Chemical compound CC1SCC(NC2=O)C(=O)NC(CC(N)=O)C(=O)NC(C(=O)NC(CCCCN)C(=O)NC(C(C)CC)C(=O)NC(=C)C(=O)NC(CCCCN)C(O)=O)CSC(C)C2NC(=O)C(CC(C)C)NC(=O)C1NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C1NC(=O)C(=C/C)/NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C2NC(=O)CNC(=O)C3CCCN3C(=O)C(NC(=O)C3NC(=O)C(CC(C)C)NC(=O)C(=C)NC(=O)C(CCC(O)=O)NC(=O)C(NC(=O)C(CCCCN)NC(=O)C(N)CC=4C5=CC=CC=C5NC=4)CSC3)C(C)SC2)C(C)C)C(C)SC1)CC1=CC=CC=C1 WPLOVIFNBMNBPD-ATHMIXSHSA-N 0.000 claims 1
- 230000006794 tachycardia Effects 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 201000002510 thyroid cancer Diseases 0.000 claims 1
- 210000001685 thyroid gland Anatomy 0.000 claims 1
- 239000005495 thyroid hormone Substances 0.000 claims 1
- 229940036555 thyroid hormone Drugs 0.000 claims 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2024076310A JP2024105460A (ja) | 2018-07-02 | 2024-05-09 | ２－（３，５－ジクロロ－４－（（５－イソプロピル－６－オキソ－１，６－ジヒドロピリダジン－３－イル）オキシ）フェニル）－３，５－ジオキソ－２，３，４，５－テトラヒドロ－１，２，４－トリアジン－６－カルボニトリルの固体形態 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201862692914P | 2018-07-02 | 2018-07-02 | |
| US62/692,914 | 2018-07-02 | ||
| PCT/US2019/040276 WO2020010068A1 (en) | 2018-07-02 | 2019-07-02 | Solid forms of 2-(3,5-dichloro-4-((5-isopropyl-6-oxo-1,6-dihydropyridazin-3-yl)oxy)phenyl)-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carbonitrile |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2024076310A Division JP2024105460A (ja) | 2018-07-02 | 2024-05-09 | ２－（３，５－ジクロロ－４－（（５－イソプロピル－６－オキソ－１，６－ジヒドロピリダジン－３－イル）オキシ）フェニル）－３，５－ジオキソ－２，３，４，５－テトラヒドロ－１，２，４－トリアジン－６－カルボニトリルの固体形態 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2021530456A JP2021530456A (ja) | 2021-11-11 |
| JPWO2020010068A5 true JPWO2020010068A5 (enExample) | 2022-07-08 |
Family
ID=67441642
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020572517A Pending JP2021530456A (ja) | 2018-07-02 | 2019-07-02 | ２−（３，５−ジクロロ−４−（（５−イソプロピル−６−オキソ−１，６−ジヒドロピリダジン−３−イル）オキシ）フェニル）−３，５−ジオキソ−２，３，４，５−テトラヒドロ−１，２，４−トリアジン−６−カルボニトリルの固体形態 |
| JP2024076310A Pending JP2024105460A (ja) | 2018-07-02 | 2024-05-09 | ２－（３，５－ジクロロ－４－（（５－イソプロピル－６－オキソ－１，６－ジヒドロピリダジン－３－イル）オキシ）フェニル）－３，５－ジオキソ－２，３，４，５－テトラヒドロ－１，２，４－トリアジン－６－カルボニトリルの固体形態 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2024076310A Pending JP2024105460A (ja) | 2018-07-02 | 2024-05-09 | ２－（３，５－ジクロロ－４－（（５－イソプロピル－６－オキソ－１，６－ジヒドロピリダジン－３－イル）オキシ）フェニル）－３，５－ジオキソ－２，３，４，５－テトラヒドロ－１，２，４－トリアジン－６－カルボニトリルの固体形態 |
Country Status (12)
| Country | Link |
|---|---|
| US (3) | US20210122740A1 (enExample) |
| EP (2) | EP3818057A1 (enExample) |
| JP (2) | JP2021530456A (enExample) |
| KR (2) | KR20250167140A (enExample) |
| CN (1) | CN112638904A (enExample) |
| AR (1) | AR115666A1 (enExample) |
| AU (2) | AU2019298236A1 (enExample) |
| CA (1) | CA3104860A1 (enExample) |
| IL (2) | IL321116A (enExample) |
| MX (3) | MX2021000107A (enExample) |
| TW (1) | TW202019914A (enExample) |
| WO (1) | WO2020010068A1 (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL314360B2 (en) | 2012-09-17 | 2025-09-01 | F Hoffmann La Roche Ltd | Method for the synthesis of thyroid hormone analogs and their polymorphs |
| KR20190109387A (ko) | 2016-10-18 | 2019-09-25 | 마드리갈 파마슈티칼스, 인크. | Thr-베타 아고니스트로 간 질환 또는 지질 질환을 치료하는 방법 |
| CN113474335B (zh) * | 2019-02-21 | 2024-12-03 | 南京瑞捷医药科技有限公司 | 化合物及其作为甲状腺激素受体激动剂的用途 |
| KR20220017917A (ko) | 2019-05-08 | 2022-02-14 | 알리고스 테라퓨틱스 인코포레이티드 | Thr-베타의 조절제 및 이의 사용 방법 |
| WO2021063367A1 (zh) * | 2019-09-30 | 2021-04-08 | 苏州科睿思制药有限公司 | 一种Resmetirom晶型及其制备方法和用途 |
| WO2021129465A1 (zh) | 2019-12-26 | 2021-07-01 | 苏州科睿思制药有限公司 | 一种Resmetirom晶型及其制备方法和用途 |
| EP4286377A4 (en) * | 2020-09-10 | 2024-10-09 | Crystal Pharmaceutical (Suzhou) Co., Ltd. | CRYSTALLINE FORM OF RESMETIROM, ITS PREPARATION METHOD AND ITS USE |
| CA3195789A1 (en) | 2020-10-19 | 2022-04-28 | Teva Pharmaceuticals International Gmbh | Solid state forms of resmetirom |
| TW202245775A (zh) * | 2021-02-01 | 2022-12-01 | 美商瑪德瑞高製藥公司 | 用於治療肝病症或脂質病症之瑞舒伐他汀（Ｒｏｓｕｖａｓｔａｔｉｎ）和瑞司美替隆（Ｒｅｓｍｅｔｉｒｏｍ）的治療組合 |
| CN114907327A (zh) * | 2021-02-10 | 2022-08-16 | 杭州领业医药科技有限公司 | Resmetirom的晶型及其制备方法和用途 |
| US20240218009A1 (en) * | 2021-04-21 | 2024-07-04 | Merck Sharp & Dohme Llc | Novel forms of cyclic dinucleotide compounds |
| CN118871113A (zh) * | 2021-11-11 | 2024-10-29 | 拓臻制药公司 | 使用THR-β激动剂的肝脏病症的治疗 |
| US20240423992A1 (en) | 2023-06-22 | 2024-12-26 | Madrigal Pharmaceuticals, Inc. | Biomarkers for treating liver disorders with thr-b agonists and related uses |
| WO2025011259A1 (zh) * | 2023-07-07 | 2025-01-16 | 苏州科睿思制药有限公司 | 瑞司美替罗的晶型及其制备方法和用途 |
| CN119613386A (zh) * | 2023-09-14 | 2025-03-14 | 杭州科巢生物科技有限公司 | 一种瑞司美替罗1,4-二氧六环溶剂化合物及其制备方法 |
| WO2025083699A2 (en) | 2023-10-16 | 2025-04-24 | Cipla Limited | Resmetirom polymorphs and process thereof |
| US12377104B1 (en) | 2024-02-06 | 2025-08-05 | Madrigal Pharmaceuticals, Inc. | Methods for treating a fatty liver disease |
| WO2025171032A1 (en) | 2024-02-06 | 2025-08-14 | Madrigal Pharmaceuticals, Inc. | Methods for treating a fatty liver disease |
| WO2025172958A1 (en) * | 2024-02-16 | 2025-08-21 | Metrochem Api Pvt Ltd | Solid state forms of resmetirom |
| WO2025231587A1 (zh) * | 2024-05-06 | 2025-11-13 | 杭州科巢生物科技有限公司 | 一种瑞司美替罗无水晶型ch及其制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2930501A (en) * | 2000-01-07 | 2001-07-24 | Transform Pharmaceuticals, Inc. | High-throughput formation, identification, and analysis of diverse solid-forms |
| JP5000649B2 (ja) * | 2005-07-21 | 2012-08-15 | エフ．ホフマン−ラ ロシュ アーゲー | 甲状腺ホルモン受容体アゴニストとしてのピリダジノン誘導体 |
| IL314360B2 (en) * | 2012-09-17 | 2025-09-01 | F Hoffmann La Roche Ltd | Method for the synthesis of thyroid hormone analogs and their polymorphs |
| KR20190109387A (ko) * | 2016-10-18 | 2019-09-25 | 마드리갈 파마슈티칼스, 인크. | Thr-베타 아고니스트로 간 질환 또는 지질 질환을 치료하는 방법 |
-
2019
- 2019-07-01 AR ARP190101846A patent/AR115666A1/es unknown
- 2019-07-01 TW TW108123112A patent/TW202019914A/zh unknown
- 2019-07-02 MX MX2021000107A patent/MX2021000107A/es unknown
- 2019-07-02 IL IL321116A patent/IL321116A/en unknown
- 2019-07-02 JP JP2020572517A patent/JP2021530456A/ja active Pending
- 2019-07-02 AU AU2019298236A patent/AU2019298236A1/en not_active Abandoned
- 2019-07-02 EP EP19745399.6A patent/EP3818057A1/en not_active Withdrawn
- 2019-07-02 US US17/257,070 patent/US20210122740A1/en not_active Abandoned
- 2019-07-02 CA CA3104860A patent/CA3104860A1/en active Pending
- 2019-07-02 KR KR1020257038532A patent/KR20250167140A/ko active Pending
- 2019-07-02 CN CN201980056826.0A patent/CN112638904A/zh active Pending
- 2019-07-02 KR KR1020217003360A patent/KR102890565B1/ko active Active
- 2019-07-02 WO PCT/US2019/040276 patent/WO2020010068A1/en not_active Ceased
- 2019-07-02 EP EP24214548.0A patent/EP4552643A3/en active Pending
-
2020
- 2020-12-23 IL IL279700A patent/IL279700A/en unknown
-
2021
- 2021-01-06 MX MX2023009701A patent/MX2023009701A/es unknown
- 2021-01-06 MX MX2024013198A patent/MX2024013198A/es unknown
-
2024
- 2024-05-09 JP JP2024076310A patent/JP2024105460A/ja active Pending
- 2024-11-15 US US18/949,309 patent/US20250074898A1/en active Pending
-
2025
- 2025-01-10 AU AU2025200189A patent/AU2025200189A1/en active Pending
- 2025-08-19 US US19/303,585 patent/US20250368626A1/en active Pending
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