JP2015535817A5 - - Google Patents
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- JP2015535817A5 JP2015535817A5 JP2015532148A JP2015532148A JP2015535817A5 JP 2015535817 A5 JP2015535817 A5 JP 2015535817A5 JP 2015532148 A JP2015532148 A JP 2015532148A JP 2015532148 A JP2015532148 A JP 2015532148A JP 2015535817 A5 JP2015535817 A5 JP 2015535817A5
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- JP
- Japan
- Prior art keywords
- compound
- formula
- temperature
- group
- dichloro
- 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.)
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- 150000001875 compounds Chemical class 0.000 claims 17
- 238000000034 method Methods 0.000 claims 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 15
- 229940126062 Compound A Drugs 0.000 claims 9
- 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 9
- 235000001014 amino acid Nutrition 0.000 claims 6
- 150000001413 amino acids Chemical class 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 5
- 239000012453 solvate Substances 0.000 claims 5
- -1 3,5-dichloro-4-((5-isopropyl-6-oxo-1,6-dihydropyridazin-3-yl) oxy) phenyl Chemical group 0.000 claims 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical group CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 239000012065 filter cake Substances 0.000 claims 4
- 238000000634 powder X-ray diffraction Methods 0.000 claims 4
- 238000006467 substitution reaction Methods 0.000 claims 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical group [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 claims 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- GUSWJGOYDXFJSI-UHFFFAOYSA-N 3,6-dichloropyridazine Chemical compound ClC1=CC=C(Cl)N=N1 GUSWJGOYDXFJSI-UHFFFAOYSA-N 0.000 claims 2
- KGEXISHTCZHGFT-UHFFFAOYSA-N 4-azaniumyl-2,6-dichlorophenolate Chemical compound NC1=CC(Cl)=C(O)C(Cl)=C1 KGEXISHTCZHGFT-UHFFFAOYSA-N 0.000 claims 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 2
- 239000004475 Arginine Substances 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 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
- 239000002841 Lewis acid Substances 0.000 claims 2
- LJMFFFZEUKITIM-UHFFFAOYSA-N N#CC1=CNCNN1 Chemical compound N#CC1=CNCNN1 LJMFFFZEUKITIM-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
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 125000006242 amine protecting group Chemical group 0.000 claims 2
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 238000001816 cooling Methods 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 238000010438 heat treatment Methods 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 230000007062 hydrolysis Effects 0.000 claims 2
- 238000006460 hydrolysis reaction Methods 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 150000007517 lewis acids Chemical class 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 229910000000 metal hydroxide Inorganic materials 0.000 claims 2
- 150000004692 metal hydroxides Chemical class 0.000 claims 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
- 230000035772 mutation Effects 0.000 claims 2
- 239000007800 oxidant agent Substances 0.000 claims 2
- 239000003880 polar aprotic solvent Substances 0.000 claims 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims 2
- FDBYIYFVSAHJLY-UHFFFAOYSA-N resmetirom Chemical compound N1C(=O)C(C(C)C)=CC(OC=2C(=CC(=CC=2Cl)N2C(NC(=O)C(C#N)=N2)=O)Cl)=N1 FDBYIYFVSAHJLY-UHFFFAOYSA-N 0.000 claims 2
- 125000006017 1-propenyl group Chemical group 0.000 claims 1
- LCBMEKQYZVCBOT-UHFFFAOYSA-N 3,5-dichloro-4-(6-chloropyridazin-3-yl)oxyaniline Chemical compound ClC1=CC(N)=CC(Cl)=C1OC1=CC=C(Cl)N=N1 LCBMEKQYZVCBOT-UHFFFAOYSA-N 0.000 claims 1
- PFQNEKHHAFIRRV-UHFFFAOYSA-N 3-(4-amino-2,6-dichlorophenoxy)-5-propan-2-yl-1h-pyridazin-6-one Chemical compound N1C(=O)C(C(C)C)=CC(OC=2C(=CC(N)=CC=2Cl)Cl)=N1 PFQNEKHHAFIRRV-UHFFFAOYSA-N 0.000 claims 1
- KVMHBQHWMVEVRZ-UHFFFAOYSA-N 5-propan-2-yl-1h-pyridazin-6-one Chemical compound CC(C)C1=CC=NNC1=O KVMHBQHWMVEVRZ-UHFFFAOYSA-N 0.000 claims 1
- 206010059245 Angiopathy Diseases 0.000 claims 1
- 201000001320 Atherosclerosis 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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- HKINNOVSZZVYGX-UHFFFAOYSA-N C1=CC(=CC=C1N(Cl)Cl)OC2=NN=C(C=C2)Cl Chemical compound C1=CC(=CC=C1N(Cl)Cl)OC2=NN=C(C=C2)Cl HKINNOVSZZVYGX-UHFFFAOYSA-N 0.000 claims 1
- 206010011878 Deafness Diseases 0.000 claims 1
- 208000004930 Fatty Liver Diseases 0.000 claims 1
- 206010018498 Goitre 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
- 208000020358 Learning disease Diseases 0.000 claims 1
- 208000036626 Mental retardation Diseases 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 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
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 239000003929 acidic solution Substances 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 210000000988 bone and bone Anatomy 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 230000007850 degeneration Effects 0.000 claims 1
- 230000003111 delayed effect Effects 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- HSOGVWWWGVFXGF-UHFFFAOYSA-N ethyl n-(2-cyanoacetyl)carbamate Chemical compound CCOC(=O)NC(=O)CC#N HSOGVWWWGVFXGF-UHFFFAOYSA-N 0.000 claims 1
- 208000010706 fatty liver disease Diseases 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 claims 1
- 201000003872 goiter Diseases 0.000 claims 1
- 125000001475 halogen functional group Chemical group 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
- 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
- 201000003723 learning disability Diseases 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 230000000926 neurological effect Effects 0.000 claims 1
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims 1
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims 1
- 235000011056 potassium acetate Nutrition 0.000 claims 1
- 208000020016 psychiatric disease Diseases 0.000 claims 1
- 208000037922 refractory disease Diseases 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 231100000240 steatosis hepatitis Toxicity 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- 230000006794 tachycardia Effects 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
- 208000019553 vascular disease Diseases 0.000 claims 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2019154299A JP6899413B2 (ja) | 2012-09-17 | 2019-08-27 | 甲状腺ホルモンアナログ及びその多形体の合成方法 |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261702137P | 2012-09-17 | 2012-09-17 | |
| US61/702,137 | 2012-09-17 | ||
| US201361790432P | 2013-03-15 | 2013-03-15 | |
| US61/790,432 | 2013-03-15 | ||
| PCT/US2013/060177 WO2014043706A1 (en) | 2012-09-17 | 2013-09-17 | Method of synthesizing thyroid hormone analogs and polymorphs thereof |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017249107A Division JP6532931B2 (ja) | 2012-09-17 | 2017-12-26 | 甲状腺ホルモンアナログ及びその多形体の合成方法 |
| JP2019154299A Division JP6899413B2 (ja) | 2012-09-17 | 2019-08-27 | 甲状腺ホルモンアナログ及びその多形体の合成方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015535817A JP2015535817A (ja) | 2015-12-17 |
| JP2015535817A5 true JP2015535817A5 (enExample) | 2016-11-04 |
| JP6616688B2 JP6616688B2 (ja) | 2019-12-04 |
Family
ID=50278769
Family Applications (8)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015532148A Active JP6616688B2 (ja) | 2012-09-17 | 2013-09-17 | 甲状腺ホルモンアナログ及びその多形体の合成方法 |
| JP2017249107A Active JP6532931B2 (ja) | 2012-09-17 | 2017-12-26 | 甲状腺ホルモンアナログ及びその多形体の合成方法 |
| JP2018217045A Active JP6765408B2 (ja) | 2012-09-17 | 2018-11-20 | 甲状腺ホルモンアナログ及びその多形体の合成方法 |
| JP2019154299A Active JP6899413B2 (ja) | 2012-09-17 | 2019-08-27 | 甲状腺ホルモンアナログ及びその多形体の合成方法 |
| JP2020020343A Active JP7038745B2 (ja) | 2012-09-17 | 2020-02-10 | 甲状腺ホルモンアナログ及びその多形体の合成方法 |
| JP2022034154A Active JP7436542B2 (ja) | 2012-09-17 | 2022-03-07 | 甲状腺ホルモンアナログ及びその多形体の合成方法 |
| JP2024016915A Pending JP2024056793A (ja) | 2012-09-17 | 2024-02-07 | 甲状腺ホルモンアナログ及びその多形体の合成方法 |
| JP2025145966A Pending JP2025179154A (ja) | 2012-09-17 | 2025-09-03 | 甲状腺ホルモンアナログ及びその多形体の合成方法 |
Family Applications After (7)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017249107A Active JP6532931B2 (ja) | 2012-09-17 | 2017-12-26 | 甲状腺ホルモンアナログ及びその多形体の合成方法 |
| JP2018217045A Active JP6765408B2 (ja) | 2012-09-17 | 2018-11-20 | 甲状腺ホルモンアナログ及びその多形体の合成方法 |
| JP2019154299A Active JP6899413B2 (ja) | 2012-09-17 | 2019-08-27 | 甲状腺ホルモンアナログ及びその多形体の合成方法 |
| JP2020020343A Active JP7038745B2 (ja) | 2012-09-17 | 2020-02-10 | 甲状腺ホルモンアナログ及びその多形体の合成方法 |
| JP2022034154A Active JP7436542B2 (ja) | 2012-09-17 | 2022-03-07 | 甲状腺ホルモンアナログ及びその多形体の合成方法 |
| JP2024016915A Pending JP2024056793A (ja) | 2012-09-17 | 2024-02-07 | 甲状腺ホルモンアナログ及びその多形体の合成方法 |
| JP2025145966A Pending JP2025179154A (ja) | 2012-09-17 | 2025-09-03 | 甲状腺ホルモンアナログ及びその多形体の合成方法 |
Country Status (23)
| Country | Link |
|---|---|
| US (8) | US9266861B2 (enExample) |
| EP (4) | EP3689853B1 (enExample) |
| JP (8) | JP6616688B2 (enExample) |
| KR (4) | KR102138750B1 (enExample) |
| CN (2) | CN108101851A (enExample) |
| AR (1) | AR092872A1 (enExample) |
| AU (1) | AU2013315017C1 (enExample) |
| BR (2) | BR122021024202B1 (enExample) |
| CA (3) | CA3111317C (enExample) |
| DK (3) | DK2895466T3 (enExample) |
| ES (2) | ES2795450T3 (enExample) |
| FI (1) | FI4406594T3 (enExample) |
| IL (7) | IL320269A (enExample) |
| IN (1) | IN2015DN03133A (enExample) |
| MX (2) | MX395148B (enExample) |
| MY (1) | MY170520A (enExample) |
| NZ (2) | NZ705827A (enExample) |
| PT (1) | PT4406594T (enExample) |
| RU (2) | RU2668960C2 (enExample) |
| SG (3) | SG10201705984XA (enExample) |
| TW (4) | TWI804870B (enExample) |
| WO (1) | WO2014043706A1 (enExample) |
| ZA (1) | ZA201501795B (enExample) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA3111317C (en) | 2012-09-17 | 2023-08-29 | F. Hoffmann-La Roche Ltd. | Method of synthesizing thyroid hormone analogs and polymorphs thereof |
| AU2017346871B2 (en) | 2016-10-18 | 2023-08-03 | Madrigal Pharmaceuticals, Inc. | Methods of treating liver disorders or lipid disorders with a THR-beta agonist |
| CN109574995B (zh) * | 2018-01-23 | 2020-07-24 | 深圳市塔吉瑞生物医药有限公司 | 取代的哒嗪酮化合物 |
| US11964964B2 (en) | 2018-06-12 | 2024-04-23 | Xizang Haisco Pharmaceutical Co., Ltd. | Thyroid hormone receptor agonists and uses thereof |
| US20210292304A1 (en) * | 2018-06-22 | 2021-09-23 | Hinova Pharmaceuticals Inc. | Deuterated mgl-3196 compound and use thereof |
| TW202019914A (zh) * | 2018-07-02 | 2020-06-01 | 美商瑪德瑞高製藥公司 | 2-(3,5-二氯-4-((5-異丙基-6-側氧基-1,6-二氫噠嗪-3-基)氧)苯基)-3,5-二側氧基-2,3,4,5-四氫-1,2,4-三嗪-6-腈之固體型式 |
| AU2019359141A1 (en) | 2018-10-12 | 2021-04-22 | InventisBio Co., Ltd. | Thyroid hormone receptor agonists |
| CN121081472A (zh) | 2018-12-13 | 2025-12-09 | 拓臻股份有限公司 | 一种THRβ受体激动剂化合物及其制备方法和用途 |
| EP3927693A4 (en) * | 2019-02-21 | 2023-04-05 | Nanjing Ruijie Pharma Co., Ltd. | NOVEL COMPOUNDS AND THEIR USES AS THYROID HORMONE RECEPTOR AGONISTS |
| AU2020267576B2 (en) | 2019-05-08 | 2025-03-13 | Aligos Therapeutics, Inc. | Modulators of THR-β and methods of use thereof |
| WO2020228577A1 (zh) * | 2019-05-10 | 2020-11-19 | 深圳微芯生物科技股份有限公司 | 一种哒嗪酮衍生物及其应用 |
| CN114174282A (zh) * | 2019-05-29 | 2022-03-11 | 南京明德新药研发有限公司 | 作为甲状腺素受体-β激动剂的哒嗪酮类衍生物及其应用 |
| WO2021043185A1 (en) * | 2019-09-04 | 2021-03-11 | Sunshine Lake Pharma Co., Ltd. | A compound as a thyroid hormone beta receptor agonist and use thereof |
| CA3154391A1 (en) | 2019-09-12 | 2021-03-18 | Terns Pharmaceuticals, Inc. | Thyroid hormone receptor beta agonist compounds |
| 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 |
| CN112707892A (zh) * | 2019-10-24 | 2021-04-27 | 苏州泽璟生物制药股份有限公司 | 哒嗪酮或哒嗪类化合物及其衍生物和药物组合物 |
| CA3158379A1 (en) * | 2019-11-26 | 2021-06-03 | Hejun Lv | 1,2,4-triazine-3,5-dione compound, preparation method therefor, and application thereof |
| WO2021121210A1 (zh) * | 2019-12-16 | 2021-06-24 | 江苏恒瑞医药股份有限公司 | 并环类衍生物、其制备方法及其在医药上的应用 |
| 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 |
| US20230339911A1 (en) * | 2020-08-27 | 2023-10-26 | InventisBio Co., Ltd. | Pyridazinone compounds |
| EP4286377A4 (en) * | 2020-09-10 | 2024-10-09 | Crystal Pharmaceutical (Suzhou) Co., Ltd. | CRYSTALLINE FORM OF RESMETIROM, ITS PREPARATION METHOD AND ITS USE |
| WO2022086894A1 (en) | 2020-10-19 | 2022-04-28 | Teva Pharmaceuticals International Gmbh | Solid state forms of resmetirom |
| CN114437042A (zh) * | 2020-11-03 | 2022-05-06 | 深圳微芯生物科技股份有限公司 | 酞嗪类化合物的晶型及其制备方法 |
| CN114437034A (zh) * | 2020-11-06 | 2022-05-06 | 深圳微芯生物科技股份有限公司 | 一种酞嗪类化合物的可药用盐、晶型及其制备方法 |
| EP4284373A1 (en) * | 2021-02-01 | 2023-12-06 | Madrigal Pharmaceuticals, Inc. | Therapeutic combinations of rosuvastatin and resmetirom for the treatment of liver disorders or lipid disorders |
| 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 |
| CN115073429A (zh) * | 2021-03-15 | 2022-09-20 | 昆药集团股份有限公司 | 一种1,2,4-三嗪-3,5-二酮类化合物的盐型、晶型及其制备方法 |
| MX2024003967A (es) | 2021-09-27 | 2024-06-03 | Madrigal Pharmaceuticals Inc | Resmetirom para reducir el volumen del higado. |
| WO2024165571A2 (en) | 2023-02-06 | 2024-08-15 | E-Therapeutics Plc | Inhibitors of expression and/or function |
| KR20250166323A (ko) | 2023-04-07 | 2025-11-27 | 테른스 파마슈티칼스, 인크. | 간 장애 또는 심장대사 질환의 치료에 사용하기 위한 thr베타 효현제 및 glp-1r 효현제를 포함하는 조합 |
| CN116768802B (zh) * | 2023-05-25 | 2025-11-21 | 杭州科巢生物科技有限公司 | 一种瑞司美替罗的合成方法 |
| WO2024263714A1 (en) | 2023-06-22 | 2024-12-26 | Madrigal Pharmaceuticals, Inc. | BIOMARKERS FOR TREATING LIVER DISORDERS WITH THR-β AGONISTS AND RELATED USES |
| 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 |
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