JP2015522616A5 - - Google Patents
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- JP2015522616A5 JP2015522616A5 JP2015523160A JP2015523160A JP2015522616A5 JP 2015522616 A5 JP2015522616 A5 JP 2015522616A5 JP 2015523160 A JP2015523160 A JP 2015523160A JP 2015523160 A JP2015523160 A JP 2015523160A JP 2015522616 A5 JP2015522616 A5 JP 2015522616A5
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- JP
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- Prior art keywords
- compound
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- salt
- diffractogram
- pharmaceutical composition
- 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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- 229940126062 Compound A Drugs 0.000 claims description 145
- 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 description 145
- 239000008194 pharmaceutical composition Substances 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 16
- 159000000000 sodium salts Chemical class 0.000 claims description 15
- 238000000113 differential scanning calorimetry Methods 0.000 claims description 13
- 238000001938 differential scanning calorimetry curve Methods 0.000 claims description 13
- 239000000843 powder Substances 0.000 claims description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 10
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 description 25
- 125000002059 L-arginyl group Chemical class O=C([*])[C@](N([H])[H])([H])C([H])([H])C([H])([H])C([H])([H])N([H])C(=N[H])N([H])[H] 0.000 description 9
- 150000008545 L-lysines Chemical class 0.000 description 9
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 9
- 150000002169 ethanolamines Chemical class 0.000 description 9
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical class OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 9
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 8
- -1 L-arginine salt Chemical class 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 208000028867 ischemia Diseases 0.000 description 3
- 230000001404 mediated effect Effects 0.000 description 3
- 102000003951 Erythropoietin Human genes 0.000 description 2
- 108090000394 Erythropoietin Proteins 0.000 description 2
- 206010021143 Hypoxia Diseases 0.000 description 2
- 208000032382 Ischaemic stroke Diseases 0.000 description 2
- 102000008109 Mixed Function Oxygenases Human genes 0.000 description 2
- 108010074633 Mixed Function Oxygenases Proteins 0.000 description 2
- 229940105423 erythropoietin Drugs 0.000 description 2
- 230000007954 hypoxia Effects 0.000 description 2
- OXCMYAYHXIHQOA-UHFFFAOYSA-N potassium;[2-butyl-5-chloro-3-[[4-[2-(1,2,4-triaza-3-azanidacyclopenta-1,4-dien-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]methanol Chemical compound [K+].CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C2=N[N-]N=N2)C=C1 OXCMYAYHXIHQOA-UHFFFAOYSA-N 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- 229960000281 trometamol Drugs 0.000 description 2
- NMFQPFSIPWZZMR-UHFFFAOYSA-N 1,1,1,2,3,3-hexafluoropropan-2-ol Chemical compound FC(F)C(F)(O)C(F)(F)F NMFQPFSIPWZZMR-UHFFFAOYSA-N 0.000 description 1
- 206010054936 Cardiac cirrhosis Diseases 0.000 description 1
- 206010007559 Cardiac failure congestive Diseases 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 206010022657 Intestinal infarction Diseases 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-Lysine Natural products NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- 235000019766 L-Lysine Nutrition 0.000 description 1
- 229930064664 L-arginine Natural products 0.000 description 1
- 235000014852 L-arginine Nutrition 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 208000005764 Peripheral Arterial Disease Diseases 0.000 description 1
- 208000030831 Peripheral arterial occlusive disease Diseases 0.000 description 1
- 208000010378 Pulmonary Embolism Diseases 0.000 description 1
- 206010063837 Reperfusion injury Diseases 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 208000007502 anemia Diseases 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 208000020832 chronic kidney disease Diseases 0.000 description 1
- 208000022831 chronic renal failure syndrome Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000000302 ischemic effect Effects 0.000 description 1
- 208000002780 macular degeneration Diseases 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N monoethanolamine hydrochloride Natural products NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- ULYBVEFKCOOSPY-UHFFFAOYSA-M potassium;2-[(4-hydroxy-1-methyl-7-phenoxyisoquinoline-3-carbonyl)amino]acetate Chemical compound [K+].C1=C2C(C)=NC(C(=O)NCC([O-])=O)=C(O)C2=CC=C1OC1=CC=CC=C1 ULYBVEFKCOOSPY-UHFFFAOYSA-M 0.000 description 1
- YOZBGTLTNGAVFU-UHFFFAOYSA-N roxadustat Chemical compound C1=C2C(C)=NC(C(=O)NCC(O)=O)=C(O)C2=CC=C1OC1=CC=CC=C1 YOZBGTLTNGAVFU-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 231100000827 tissue damage Toxicity 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261672191P | 2012-07-16 | 2012-07-16 | |
| US61/672,191 | 2012-07-16 | ||
| US201361768297P | 2013-02-22 | 2013-02-22 | |
| US61/768,297 | 2013-02-22 | ||
| US201361832566P | 2013-06-07 | 2013-06-07 | |
| US61/832,566 | 2013-06-07 | ||
| PCT/US2013/050539 WO2014014835A2 (en) | 2012-07-16 | 2013-07-15 | Crystalline forms of a prolyl hydroxylase inhibitor |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017203509A Division JP2018009034A (ja) | 2012-07-16 | 2017-10-20 | プロリルヒドロキシラーゼ阻害剤の結晶形態 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015522616A JP2015522616A (ja) | 2015-08-06 |
| JP2015522616A5 true JP2015522616A5 (enExample) | 2016-09-01 |
| JP6491093B2 JP6491093B2 (ja) | 2019-03-27 |
Family
ID=48857025
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015523160A Active JP6491093B2 (ja) | 2012-07-16 | 2013-07-15 | プロリルヒドロキシラーゼ阻害剤の結晶形態 |
| JP2017203509A Pending JP2018009034A (ja) | 2012-07-16 | 2017-10-20 | プロリルヒドロキシラーゼ阻害剤の結晶形態 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017203509A Pending JP2018009034A (ja) | 2012-07-16 | 2017-10-20 | プロリルヒドロキシラーゼ阻害剤の結晶形態 |
Country Status (29)
| Country | Link |
|---|---|
| US (5) | US9115085B2 (enExample) |
| EP (3) | EP4029854A1 (enExample) |
| JP (2) | JP6491093B2 (enExample) |
| KR (4) | KR20210130849A (enExample) |
| CN (9) | CN107382860A (enExample) |
| AU (1) | AU2013290438C1 (enExample) |
| BR (1) | BR112015001101A2 (enExample) |
| CA (1) | CA2879242C (enExample) |
| CY (2) | CY1120805T1 (enExample) |
| DK (2) | DK2872488T3 (enExample) |
| ES (2) | ES2689430T3 (enExample) |
| FR (1) | FR22C1030I2 (enExample) |
| HK (1) | HK1243409A1 (enExample) |
| HR (2) | HRP20220182T1 (enExample) |
| HU (2) | HUE057925T2 (enExample) |
| IL (1) | IL236626B (enExample) |
| IN (1) | IN2015KN00262A (enExample) |
| LT (3) | LT3470397T (enExample) |
| MX (1) | MX355428B (enExample) |
| MY (1) | MY182428A (enExample) |
| NO (1) | NO2022024I1 (enExample) |
| NZ (1) | NZ704662A (enExample) |
| PL (2) | PL3470397T3 (enExample) |
| PT (2) | PT2872488T (enExample) |
| RS (2) | RS57795B1 (enExample) |
| SG (3) | SG10201700873UA (enExample) |
| SI (2) | SI3470397T1 (enExample) |
| SM (2) | SMT202200095T1 (enExample) |
| WO (1) | WO2014014835A2 (enExample) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL1644336T3 (pl) | 2003-06-06 | 2011-07-29 | Fibrogen Inc | Związki heteroarylowe zawierające azot i ich zastosowanie w zwiększaniu poziomu endogennej erytropoetyny |
| EP2370422B1 (en) | 2008-11-14 | 2019-06-05 | Fibrogen, Inc. | Thiochromene derivatives as hif hydroxylase inhibitors |
| EP2670750B1 (en) | 2011-02-02 | 2016-09-14 | Fibrogen, Inc. | Naphthyridine derivatives as inhibitors of hypoxia inducible factor |
| CA2879238C (en) | 2012-07-16 | 2021-08-10 | Fibrogen, Inc. | Process for making isoquinoline compounds |
| SG10201700873UA (en) | 2012-07-16 | 2017-04-27 | Fibrogen Inc | Crystalline forms of the prolyl hydroxylase inhibitor [(4-hydroxy-1-methyl-7-phenoxy-isoquinoline-3-carbonyl)-amino]-acetic acid |
| US8883823B2 (en) | 2012-07-16 | 2014-11-11 | Fibrogen, Inc. | Crystalline forms of a prolyl hydroxylase inhibitor |
| CN110448537A (zh) | 2013-06-06 | 2019-11-15 | 菲布罗根有限公司 | Hif羟化酶抑制剂的药物制剂 |
| CN103694172A (zh) * | 2013-12-26 | 2014-04-02 | 辽宁亿灵科创生物医药科技有限公司 | 含氮杂芳基化合物的衍生物 |
| WO2016045125A1 (en) | 2014-09-28 | 2016-03-31 | Merck Sharp & Dohme Corp. | Inhibitors of hif prolyl hydroxylase |
| CN104892509B (zh) * | 2015-06-04 | 2018-03-09 | 苏州明锐医药科技有限公司 | 诺得司他的制备方法 |
| CN106916105A (zh) * | 2015-12-28 | 2017-07-04 | 徐州万邦金桥制药有限公司 | 一种纯化可博美的方法 |
| US11510917B2 (en) | 2016-02-19 | 2022-11-29 | Cornell University | HIF-stabilization and prevention of hyperoxia-induced neonatal lung disease |
| CN106187888A (zh) * | 2016-07-18 | 2016-12-07 | 江苏德源药业股份有限公司 | Fg‑4592单晶及其制备方法 |
| CN108017583B (zh) * | 2016-11-01 | 2021-04-06 | 徐州万邦金桥制药有限公司 | 一种可博美的制备方法 |
| CN107382986B (zh) * | 2017-08-02 | 2022-09-20 | 江苏艾立康医药科技有限公司 | 4-羟基-1-甲基异喹啉衍生物及其在增加内源性促红细胞生成素中的用途 |
| CA3072601A1 (en) * | 2017-08-11 | 2019-02-14 | Dr. Reddy's Laboratories Limited | Polymorphs and co-crystals of roxadustat |
| WO2019042485A1 (en) | 2017-08-30 | 2019-03-07 | Zentiva, K.S. | FORMS IN THE STRONG STATE OF ROXADUSTAT |
| CA3074529C (en) | 2017-09-04 | 2022-07-05 | Sandoz Ag | Co-crystal of roxadustat with l-proline and uses thereof |
| US11363815B2 (en) | 2018-06-05 | 2022-06-21 | Shenyang University Of Chemical Technology | Trifluoroethyl thioether (sulfoxide) substituted benzene compound and use thereof |
| CN111320583A (zh) * | 2018-12-14 | 2020-06-23 | 广东东阳光药业有限公司 | 诺德司他新晶型及其制备方法 |
| CN109369525A (zh) * | 2018-12-29 | 2019-02-22 | 安礼特（上海）医药科技有限公司 | 罗沙司它的新晶型及其制备方法 |
| WO2020217190A1 (en) * | 2019-04-26 | 2020-10-29 | Dr. Reddy’S Laboratories Limited | Process for the purification of roxadustat |
| CN112679428A (zh) * | 2019-10-17 | 2021-04-20 | 罗欣药业(上海)有限公司 | 罗沙司他新晶型及其制备方法 |
| CN114344301B (zh) * | 2019-10-22 | 2023-06-23 | 苏州科睿思制药有限公司 | 一种低氧诱导因子脯氨酰羟化酶抑制剂晶型 |
| CN110721185B (zh) * | 2019-11-13 | 2022-04-12 | 南京市儿童医院 | 罗沙司他用于心肌保护的用途 |
| CN112961107B (zh) * | 2019-12-13 | 2024-06-25 | 罗欣药业(上海)有限公司 | 罗沙司他的晶型及其制备方法 |
| EP4121009A4 (en) * | 2020-03-17 | 2024-04-17 | Zydus Lifesciences Limited | Formulation comprising hif prolyl hydroxylase inhibitors |
| CN111205224B (zh) * | 2020-04-22 | 2020-08-25 | 南京佰麦生物技术有限公司 | 一种罗沙司他水合物的晶型及其制备方法和应用 |
| CN113754569B (zh) * | 2020-06-04 | 2024-07-02 | 四川国为制药有限公司 | 一种中间体化合物及其制备方法和用途 |
| CN111533691A (zh) * | 2020-06-08 | 2020-08-14 | 重庆三圣实业股份有限公司 | 一种罗沙司他的制备方法 |
| CN114057643B (zh) * | 2020-08-04 | 2023-02-28 | 成都苑东生物制药股份有限公司 | 一种罗沙司他共晶及其制备方法 |
| CN112500344B (zh) * | 2020-11-18 | 2022-07-01 | 江苏豪森药业集团有限公司 | 罗沙司他晶型及其制备方法 |
| CN112194624A (zh) * | 2020-11-18 | 2021-01-08 | 江苏豪森药业集团有限公司 | 一种异喹啉类化合物的晶型及其制备方法 |
| CN115724796A (zh) * | 2021-08-26 | 2023-03-03 | 成都苑东生物制药股份有限公司 | 一种罗沙司他新晶型及其制备方法 |
| CN113956200A (zh) * | 2021-12-16 | 2022-01-21 | 南京威凯尔生物医药科技有限公司 | 一种粒径控制的罗沙司他原料药的结晶工艺 |
| CN116410134A (zh) * | 2021-12-31 | 2023-07-11 | 北京济美堂医药研究有限公司 | 一种罗沙司他水合物晶体及其制备方法和应用 |
| WO2025111214A1 (en) | 2023-11-22 | 2025-05-30 | Fibrogen, Inc. | [(4-hydroxy-1-methyl-7-phenoxyisoquinoline-3- carbonyl)amino]acetic acid (roxadustat) for the treatment of anemia in subjects with myelodysplastic syndrome (mds) |
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