JP2014524920A5 - - Google Patents
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- JP2014524920A5 JP2014524920A5 JP2014520521A JP2014520521A JP2014524920A5 JP 2014524920 A5 JP2014524920 A5 JP 2014524920A5 JP 2014520521 A JP2014520521 A JP 2014520521A JP 2014520521 A JP2014520521 A JP 2014520521A JP 2014524920 A5 JP2014524920 A5 JP 2014524920A5
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- Prior art keywords
- compound
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- formula
- ray powder
- powder diffraction
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims 40
- 238000000634 powder X-ray diffraction Methods 0.000 claims 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 23
- 239000013078 crystal Substances 0.000 claims 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 12
- 239000012046 mixed solvent Substances 0.000 claims 11
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 9
- 235000019439 ethyl acetate Nutrition 0.000 claims 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 6
- 230000008018 melting Effects 0.000 claims 6
- 238000002844 melting Methods 0.000 claims 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 6
- 230000015572 biosynthetic process Effects 0.000 claims 4
- 208000035475 disorder Diseases 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 238000003786 synthesis reaction Methods 0.000 claims 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 3
- 208000007502 anemia Diseases 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000028867 ischemia Diseases 0.000 claims 3
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims 3
- 229940011051 isopropyl acetate Drugs 0.000 claims 3
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 239000002244 precipitate Substances 0.000 claims 3
- 238000010992 reflux Methods 0.000 claims 3
- BXVSAYBZSGIURM-UHFFFAOYSA-N 2-phenoxy-4h-1,3,2$l^{5}-benzodioxaphosphinine 2-oxide Chemical compound O1CC2=CC=CC=C2OP1(=O)OC1=CC=CC=C1 BXVSAYBZSGIURM-UHFFFAOYSA-N 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 2
- -1 Synthesis of Compound 5 Compound Chemical class 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 238000004587 chromatography analysis Methods 0.000 claims 2
- 229940125904 compound 1 Drugs 0.000 claims 2
- 229940125782 compound 2 Drugs 0.000 claims 2
- 229940126214 compound 3 Drugs 0.000 claims 2
- 229940125898 compound 5 Drugs 0.000 claims 2
- 238000001914 filtration Methods 0.000 claims 2
- 238000010438 heat treatment Methods 0.000 claims 2
- 239000012535 impurity Substances 0.000 claims 2
- 239000011261 inert gas Substances 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 claims 2
- 238000001556 precipitation Methods 0.000 claims 2
- 238000000746 purification Methods 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 230000002269 spontaneous effect Effects 0.000 claims 2
- 238000003756 stirring Methods 0.000 claims 2
- 238000005406 washing Methods 0.000 claims 2
- UVNPEUJXKZFWSJ-LMTQTHQJSA-N (R)-N-[(4S)-8-[6-amino-5-[(3,3-difluoro-2-oxo-1H-pyrrolo[2,3-b]pyridin-4-yl)sulfanyl]pyrazin-2-yl]-2-oxa-8-azaspiro[4.5]decan-4-yl]-2-methylpropane-2-sulfinamide Chemical compound CC(C)(C)[S@@](=O)N[C@@H]1COCC11CCN(CC1)c1cnc(Sc2ccnc3NC(=O)C(F)(F)c23)c(N)n1 UVNPEUJXKZFWSJ-LMTQTHQJSA-N 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- GNFTZDOKVXKIBK-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzohydrazide Chemical compound COCCOC1=CC=CC(C(=O)NN)=C1 GNFTZDOKVXKIBK-UHFFFAOYSA-N 0.000 claims 1
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 claims 1
- LVSVSUCJJFSWSY-UHFFFAOYSA-N C(C)(=O)OC.[N+](#[C-])CC(=O)O Chemical compound C(C)(=O)OC.[N+](#[C-])CC(=O)O LVSVSUCJJFSWSY-UHFFFAOYSA-N 0.000 claims 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 1
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 1
- 208000002903 Thalassemia Diseases 0.000 claims 1
- 229960000583 acetic acid Drugs 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 239000008346 aqueous phase Substances 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 229940125773 compound 10 Drugs 0.000 claims 1
- 239000012297 crystallization seed Substances 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 238000004821 distillation Methods 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 239000012362 glacial acetic acid Substances 0.000 claims 1
- COQRGFWWJBEXRC-UHFFFAOYSA-N hydron;methyl 2-aminoacetate;chloride Chemical compound Cl.COC(=O)CN COQRGFWWJBEXRC-UHFFFAOYSA-N 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 claims 1
- 239000012074 organic phase Substances 0.000 claims 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 claims 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims 1
- 238000011084 recovery Methods 0.000 claims 1
- 238000002390 rotary evaporation Methods 0.000 claims 1
- 239000000741 silica gel Substances 0.000 claims 1
- 229910002027 silica gel Inorganic materials 0.000 claims 1
- 208000037905 systemic hypertension Diseases 0.000 claims 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical compound CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 claims 1
- 230000029663 wound healing Effects 0.000 claims 1
- WPFRVDGFFDXCKM-UHFFFAOYSA-N COC(C(NC(c1cc(Oc2ccccc2)ccc11)=O)=C1O)=O Chemical compound COC(C(NC(c1cc(Oc2ccccc2)ccc11)=O)=C1O)=O WPFRVDGFFDXCKM-UHFFFAOYSA-N 0.000 description 1
- VCOCTEDFDWIIBJ-UHFFFAOYSA-N COC(c1c(-c2cc(Oc3ccccc3)ccc2C(O)=O)[o]cn1)=O Chemical compound COC(c1c(-c2cc(Oc3ccccc3)ccc2C(O)=O)[o]cn1)=O VCOCTEDFDWIIBJ-UHFFFAOYSA-N 0.000 description 1
- UMMWEAOVAUETLR-UHFFFAOYSA-N COC(c1nc(Cl)c(cc(cc2)Oc3ccccc3)c2c1O)=O Chemical compound COC(c1nc(Cl)c(cc(cc2)Oc3ccccc3)c2c1O)=O UMMWEAOVAUETLR-UHFFFAOYSA-N 0.000 description 1
- YOZBGTLTNGAVFU-UHFFFAOYSA-N Cc(nc1C(NCC(O)=O)=O)c(cc(cc2)Oc3ccccc3)c2c1O Chemical compound Cc(nc1C(NCC(O)=O)=O)c(cc(cc2)Oc3ccccc3)c2c1O YOZBGTLTNGAVFU-UHFFFAOYSA-N 0.000 description 1
- QSGJZCCNTOCDRI-UHFFFAOYSA-N Cc(nc1C(NCC(OC)=O)=O)c(cc(cc2)Oc3ccccc3)c2c1O Chemical compound Cc(nc1C(NCC(OC)=O)=O)c(cc(cc2)Oc3ccccc3)c2c1O QSGJZCCNTOCDRI-UHFFFAOYSA-N 0.000 description 1
- RQLQUCXIJNHBDY-UHFFFAOYSA-N Cc(nc1C(O)=O)c(cc(cc2)Oc3ccccc3)c2c1O Chemical compound Cc(nc1C(O)=O)c(cc(cc2)Oc3ccccc3)c2c1O RQLQUCXIJNHBDY-UHFFFAOYSA-N 0.000 description 1
- 0 Cc1cc(Oc2cc3c(C)nc(C(OC)=O)c(*)c3cc2)ccc1 Chemical compound Cc1cc(Oc2cc3c(C)nc(C(OC)=O)c(*)c3cc2)ccc1 0.000 description 1
- CRZSSXUMRNESCC-UHFFFAOYSA-N N#Cc(c(C#N)c1)ccc1Oc1ccccc1 Chemical compound N#Cc(c(C#N)c1)ccc1Oc1ccccc1 CRZSSXUMRNESCC-UHFFFAOYSA-N 0.000 description 1
- NTZMSBAAHBICLE-UHFFFAOYSA-N N#Cc(c(C#N)c1)ccc1[N+]([O-])=O Chemical compound N#Cc(c(C#N)c1)ccc1[N+]([O-])=O NTZMSBAAHBICLE-UHFFFAOYSA-N 0.000 description 1
- HDQBHDKNRKRCNH-UHFFFAOYSA-N O=C(c(c1c2)ccc2Oc2ccccc2)OC1=O Chemical compound O=C(c(c1c2)ccc2Oc2ccccc2)OC1=O HDQBHDKNRKRCNH-UHFFFAOYSA-N 0.000 description 1
- FKDITAXSGNKBOZ-UHFFFAOYSA-N OC(c(c(C(O)=O)c1)ccc1Oc1ccccc1)=O Chemical compound OC(c(c(C(O)=O)c1)ccc1Oc1ccccc1)=O FKDITAXSGNKBOZ-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110207175 | 2011-07-22 | ||
| CN201110207175.6 | 2011-07-22 | ||
| CN201110209657 | 2011-07-25 | ||
| CN201110209657.5 | 2011-07-25 | ||
| CN201110211297.2 | 2011-07-26 | ||
| CN201110211297 | 2011-07-26 | ||
| PCT/CN2012/079058 WO2013013609A1 (en) | 2011-07-22 | 2012-07-23 | Polymorphic forms of compounds as prolyl hydroxylase inhibitor, and uses thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014524920A JP2014524920A (ja) | 2014-09-25 |
| JP2014524920A5 true JP2014524920A5 (enExample) | 2015-09-10 |
| JP6099644B2 JP6099644B2 (ja) | 2017-03-22 |
Family
ID=47600518
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014520521A Expired - Fee Related JP6099644B2 (ja) | 2011-07-22 | 2012-07-23 | プロリルヒドロキシラーゼ阻害剤としての化合物の多形体、およびその使用 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US9206134B2 (enExample) |
| EP (1) | EP2734504B1 (enExample) |
| JP (1) | JP6099644B2 (enExample) |
| KR (1) | KR102029951B1 (enExample) |
| CN (1) | CN104024227B8 (enExample) |
| AU (1) | AU2012289429B2 (enExample) |
| CA (1) | CA2842730C (enExample) |
| ES (1) | ES2606631T3 (enExample) |
| IL (1) | IL230580B (enExample) |
| WO (1) | WO2013013609A1 (enExample) |
| ZA (1) | ZA201401310B (enExample) |
Families Citing this family (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102718708A (zh) | 2003-06-06 | 2012-10-10 | 菲布罗根有限公司 | 含氮杂芳基化合物及其在增加内源性促红细胞生成素中的用途 |
| NO2686520T3 (enExample) | 2011-06-06 | 2018-03-17 | ||
| US8883823B2 (en) | 2012-07-16 | 2014-11-11 | Fibrogen, Inc. | Crystalline forms of a prolyl hydroxylase inhibitor |
| BR112015001106B1 (pt) * | 2012-07-16 | 2021-11-09 | Fibrogen, Inc | Métodos para a produção de compostos de isoquinolina |
| CN107540607A (zh) * | 2012-07-16 | 2018-01-05 | 菲布罗根有限公司 | 脯氨酰羟化酶抑制剂的晶体形态 |
| PT3003284T (pt) | 2013-06-06 | 2020-08-10 | Fibrogen Inc | Formulações farmacêuticas de um inibidor da hidroxilase do fih |
| CA3151685A1 (en) | 2013-06-13 | 2014-12-18 | Akebia Therapeutics, Inc. | Compositions and methods for treating anemia |
| EP3068394A4 (en) | 2013-11-15 | 2017-04-26 | Akebia Therapeutics Inc. | Solid forms of {[5-(3-chlorophenyl)-3-hydroxypyridine-2-carbonyl]amino}acetic acid, compositions, and uses thereof |
| 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 |
| CA2974691A1 (en) * | 2015-01-23 | 2016-07-28 | Akebia Therapeutics, Inc. | Solid forms of 2-(5-(3-fluorophenyl)-3-hydroxypicolinamido)acetic acid, compositions, and uses thereof |
| CN106146490B (zh) * | 2015-03-27 | 2018-10-23 | 沈阳三生制药有限责任公司 | 被芳氧基或杂芳氧基取代的5-羟基-1,7-萘啶化合物、其制备方法及其制药用途 |
| US11324734B2 (en) | 2015-04-01 | 2022-05-10 | Akebia Therapeutics, Inc. | Compositions and methods for treating anemia |
| CN104910113B (zh) * | 2015-05-21 | 2017-05-10 | 中国科学院宁波材料技术与工程研究所 | 一种羟基苯酐的制备方法 |
| 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 |
| CN113694077A (zh) * | 2015-08-13 | 2021-11-26 | 索马根尼科斯公司 | 用于伤口愈合的短小发夹rna与微rna的组合物以及方法 |
| CN105130888A (zh) | 2015-10-09 | 2015-12-09 | 中国药科大学 | 炔基吡啶类脯氨酰羟化酶抑制剂、其制备方法和医药用途 |
| 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 |
| 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 |
| CZ2016627A3 (cs) | 2016-10-07 | 2018-04-18 | Zentiva, K.S. | Způsob přípravy (7-fenoxy-4-hydroxy-1-methylisochinolin-3-karbonyl)glycinu (roxadustatu) a jeho intermediátů založený na souběžném otevírání oxazolového kruhu, štěpení etheru a tvorbě iminu |
| CN107954931B (zh) * | 2016-10-17 | 2021-06-22 | 上海医药集团青岛国风药业股份有限公司 | 一种诺得司他的制备方法 |
| 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 |
| BR112020002939A2 (pt) * | 2017-08-11 | 2020-08-04 | Dr. Reddy¿S Laboratories Limited | polimorfos e cocristais de roxadustat |
| EP3679017B1 (en) * | 2017-09-04 | 2021-08-25 | Sandoz AG | Co-crystal of an orally available hif prolyl hydroxylase inhibitor |
| US20200299242A1 (en) * | 2017-12-01 | 2020-09-24 | Dr. Reddy's Laboratories Limited | Process for the preparation of roxadustat and its intermediates |
| CN109956870A (zh) | 2017-12-14 | 2019-07-02 | 南京卡文迪许生物工程技术有限公司 | 一种罗沙司他的合成方法及其中间体化合物 |
| CN108059679B (zh) * | 2017-12-27 | 2020-03-24 | 吉林大学 | 一种人源单链抗体及其应用 |
| CN110218184B (zh) * | 2018-03-01 | 2022-09-27 | 广东东阳光药业有限公司 | 诺德司他共晶及其制备方法 |
| CN110272386B (zh) * | 2018-03-16 | 2022-09-09 | 上海医药集团青岛国风药业股份有限公司 | 一种诺得司他的制备方法 |
| CN108424388B (zh) * | 2018-04-19 | 2020-08-21 | 杭州科巢生物科技有限公司 | 一种慢性贫血药物的制备方法 |
| JP7440989B2 (ja) | 2018-05-09 | 2024-02-29 | アケビア セラピューティクス インコーポレイテッド | ２－［５－（３－クロロフェニル）－３－ヒドロキシピリジン－２－カルボニル］アミノ］酢酸を調製するための方法 |
| CN110903242B (zh) * | 2018-09-14 | 2023-05-12 | 四川科伦药物研究院有限公司 | 罗沙司他中间体的制备方法 |
| 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 |
| WO2020178847A1 (en) | 2019-03-01 | 2020-09-10 | Mylan Laboratories Limited | Cocrystal of roxadustat and d-proline |
| CN109776415B (zh) * | 2019-03-07 | 2020-11-17 | 福建南方制药股份有限公司 | 一种Roxadustat中间体的制备方法 |
| CN113874350B (zh) * | 2019-04-18 | 2024-08-06 | 尼坎治疗公司 | 作为缺氧可诱导因子-2(α)抑制剂的四氢-1H-环戊二烯并[CD]茚衍生物 |
| CN109956901B (zh) * | 2019-04-25 | 2022-09-06 | 南京正大天晴制药有限公司 | 异喹啉酮类化合物的制备方法 |
| US20220340532A1 (en) | 2019-08-07 | 2022-10-27 | Teva Pharmaceuticals International Gmbh | Processes for the preparation of roxadustat and intermediates thereof |
| 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 |
| CN112679429B (zh) * | 2019-10-18 | 2023-05-05 | 上海迪赛诺化学制药有限公司 | 一种制备异喹啉酮类化合物的方法 |
| CN112679431B (zh) * | 2019-10-18 | 2023-05-05 | 上海迪赛诺化学制药有限公司 | 一种制备异喹啉酮类化合物的方法 |
| CN112679430B (zh) * | 2019-10-18 | 2023-05-05 | 上海迪赛诺化学制药有限公司 | 一种制备异喹啉酮类化合物的方法 |
| US20230112619A1 (en) * | 2019-10-18 | 2023-04-13 | Shanghai Desano Chemical Pharmaceutical Co., Ltd. | Method for preparing isoquinolinone compounds |
| WO2021077994A1 (zh) * | 2019-10-22 | 2021-04-29 | 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 |
| US11524939B2 (en) | 2019-11-13 | 2022-12-13 | Akebia Therapeutics, Inc. | Solid forms of {[5-(3-chlorophenyl)-3-hydroxypyridine-2-carbonyl]amino} acetic acid |
| 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 |
| CN113801060B (zh) | 2020-06-13 | 2025-06-27 | 苏州鹏旭医药科技有限公司 | 一种多取代异喹啉化合物的制备方法 |
| CN113816904B (zh) | 2020-06-19 | 2022-08-12 | 济川(上海)医学科技有限公司 | 一种罗沙司他及其中间体的合成方法和其中间体 |
| 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 |
| 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 |
| CN115144480B (zh) * | 2021-03-31 | 2023-11-28 | 成都倍特药业股份有限公司 | 一种从罗沙司他中间体中检测吗啉和/或四甲基甲烷二胺的方法 |
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| JPS5470285A (en) * | 1977-11-14 | 1979-06-05 | Tanabe Seiyaku Co Ltd | Production of 4-hydroxyisocarbostyryl-3-carboxylic analog |
| DE19746287A1 (de) * | 1997-10-20 | 1999-04-22 | Hoechst Marion Roussel De Gmbh | Substituierte Isochinolin-2-Carbonsäureamide, ihre Herstellung und ihre Verwendung als Arzneimittel |
| CN1518447A (zh) * | 2001-04-23 | 2004-08-04 | �������Ǵ�ѧר������� | 作为抗血管生成剂的新的苯邻二甲酰亚胺模拟物的合成和评估 |
| CN102718708A (zh) * | 2003-06-06 | 2012-10-10 | 菲布罗根有限公司 | 含氮杂芳基化合物及其在增加内源性促红细胞生成素中的用途 |
| US7189697B2 (en) | 2004-04-13 | 2007-03-13 | Trustees Of Tufts College | Compositions and uses of a galectin for treatment of dry eye syndrome |
| JP5390184B2 (ja) * | 2005-06-06 | 2014-01-15 | ファイブローゲン、インコーポレーテッド | 貧血の改良された治療方法 |
| CA2634168C (en) | 2005-12-09 | 2013-04-23 | Amgen Inc. | Quinolone based compounds exhibiting prolyl hydroxylase inhibitory activity, and compositions, and uses thereof |
| KR101446499B1 (ko) * | 2006-01-27 | 2014-10-06 | 피브로겐, 인크. | 저산소증 유발가능 인자(ｈｉｆ)를 안정시키는 시아노이소퀴놀린 화합물 |
| US20070293575A1 (en) * | 2006-06-15 | 2007-12-20 | Fibrogen, Inc. | Compounds and methods for treatment of cancer-related anemia |
| JP4311416B2 (ja) | 2006-06-30 | 2009-08-12 | 株式会社日立製作所 | 渦電流探傷法による表面欠陥長さ評価方法 |
| IN2012DN00549A (enExample) | 2009-07-15 | 2015-06-12 | Zhejiang Beta Pharma Inc |
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