JP2017511383A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2017511383A5 JP2017511383A5 JP2017505695A JP2017505695A JP2017511383A5 JP 2017511383 A5 JP2017511383 A5 JP 2017511383A5 JP 2017505695 A JP2017505695 A JP 2017505695A JP 2017505695 A JP2017505695 A JP 2017505695A JP 2017511383 A5 JP2017511383 A5 JP 2017511383A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- pharmaceutically acceptable
- compound
- type
- substituted
- 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.)
- Granted
Links
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 18
- 229930182470 glycoside Natural products 0.000 claims 18
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 18
- 150000001875 compounds Chemical class 0.000 claims 15
- 238000000034 method Methods 0.000 claims 14
- 229940002612 prodrug Drugs 0.000 claims 13
- 239000000651 prodrug Substances 0.000 claims 13
- 150000003839 salts Chemical class 0.000 claims 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 12
- 229910052799 carbon Inorganic materials 0.000 claims 12
- 229910052760 oxygen Inorganic materials 0.000 claims 11
- 125000000217 alkyl group Chemical group 0.000 claims 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims 10
- 239000003814 drug Substances 0.000 claims 10
- 239000002904 solvent Substances 0.000 claims 9
- 229940079593 drug Drugs 0.000 claims 8
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 239000000203 mixture Substances 0.000 claims 7
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 6
- -1 Z is CH 2 Inorganic materials 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 238000006243 chemical reaction Methods 0.000 claims 6
- 229910052731 fluorine Inorganic materials 0.000 claims 6
- 125000004438 haloalkoxy group Chemical group 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 238000002360 preparation method Methods 0.000 claims 6
- 125000006239 protecting group Chemical group 0.000 claims 6
- 239000003513 alkali Substances 0.000 claims 5
- 125000004429 atom Chemical group 0.000 claims 5
- 125000002619 bicyclic group Chemical group 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 4
- 229910052801 chlorine Inorganic materials 0.000 claims 4
- 239000000460 chlorine Substances 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 3
- 241000287463 Phalacrocorax Species 0.000 claims 3
- 125000003282 alkyl amino group Chemical group 0.000 claims 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 3
- 229910052794 bromium Inorganic materials 0.000 claims 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 3
- 230000006196 deacetylation Effects 0.000 claims 3
- 238000003381 deacetylation reaction Methods 0.000 claims 3
- 230000000155 isotopic effect Effects 0.000 claims 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 208000002249 Diabetes Complications Diseases 0.000 claims 2
- 206010012655 Diabetic complications Diseases 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 206010020772 Hypertension Diseases 0.000 claims 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- 102000000070 Sodium-Glucose Transport Proteins Human genes 0.000 claims 2
- 108010080361 Sodium-Glucose Transport Proteins Proteins 0.000 claims 2
- 229940127003 anti-diabetic drug Drugs 0.000 claims 2
- 239000003472 antidiabetic agent Substances 0.000 claims 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 2
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims 2
- 125000002346 iodo group Chemical group I* 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 claims 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- 229910015900 BF3 Inorganic materials 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims 1
- 238000006751 Mitsunobu reaction Methods 0.000 claims 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000008103 glucose Substances 0.000 claims 1
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims 1
- 229910052740 iodine Chemical group 0.000 claims 1
- 239000011630 iodine Chemical group 0.000 claims 1
- 208000030159 metabolic disease Diseases 0.000 claims 1
- 229940098779 methanesulfonic acid Drugs 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 239000012046 mixed solvent Substances 0.000 claims 1
- GMBXBKNMMIWUED-UHFFFAOYSA-N n-(2,2,6,6-tetramethylpiperidin-4-yl)-3-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]propanamide Chemical compound C1C(C)(C)NC(C)(C)CC1NCCC(=O)NC1CC(C)(C)NC(C)(C)C1 GMBXBKNMMIWUED-UHFFFAOYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 claims 1
- 125000001979 organolithium group Chemical group 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 claims 1
- 238000006722 reduction reaction Methods 0.000 claims 1
- 229940121377 sodium-glucose co-transporter inhibitor Drugs 0.000 claims 1
- 238000011282 treatment Methods 0.000 claims 1
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 claims 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410148116.X | 2014-04-14 | ||
| CN201410148116 | 2014-04-14 | ||
| CN201410392098.X | 2014-08-11 | ||
| CN201410392098.XA CN105001213B (zh) | 2014-04-14 | 2014-08-11 | C-芳基糖苷衍生物、其药物组合物、制备方法及应用 |
| PCT/CN2015/075651 WO2015158206A1 (zh) | 2014-04-14 | 2015-04-01 | C-芳基糖苷衍生物、其药物组合物、制备方法及应用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017511383A JP2017511383A (ja) | 2017-04-20 |
| JP2017511383A5 true JP2017511383A5 (enExample) | 2018-05-17 |
| JP6577569B2 JP6577569B2 (ja) | 2019-09-18 |
Family
ID=54323473
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017505695A Expired - Fee Related JP6577569B2 (ja) | 2014-04-14 | 2015-04-01 | Ｃ−アリールグリコシド誘導体、その薬物組成物、及び調製方法 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US9914724B2 (enExample) |
| EP (1) | EP3133071B1 (enExample) |
| JP (1) | JP6577569B2 (enExample) |
| CN (1) | CN105001213B (enExample) |
| WO (1) | WO2015158206A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105001213B (zh) | 2014-04-14 | 2020-08-28 | 上海迪诺医药科技有限公司 | C-芳基糖苷衍生物、其药物组合物、制备方法及应用 |
| CN105017236A (zh) * | 2014-04-14 | 2015-11-04 | 上海迪诺医药科技有限公司 | C-芳基糖苷衍生物、其药物组合物、制备方法及应用 |
| TN2018000020A1 (en) * | 2015-07-20 | 2019-07-08 | Genzyme Corp | Colony stimulating factor-1 receptor (csf-1r) inhibitors. |
| CN106892948B (zh) * | 2015-12-17 | 2022-07-26 | 宜昌东阳光长江药业股份有限公司 | 吡喃葡萄糖基衍生物及其在医药上的应用 |
| CN106928040A (zh) * | 2015-12-31 | 2017-07-07 | 上海医药工业研究院 | Sglt2抑制剂中间体的制备方法 |
| CN107720781B (zh) * | 2017-11-30 | 2018-07-17 | 五莲森之林海藻有限公司 | 一种盐晶颗粒提取设备 |
| CN111465598B (zh) * | 2018-03-30 | 2023-04-21 | 山东丹红制药有限公司 | 作为SGLTs抑制剂的葡糖苷类衍生物及其应用 |
| CN111471031B (zh) * | 2019-01-24 | 2023-05-16 | 北京盈科瑞创新药物研究有限公司 | 一种糖苷类衍生物及其制备方法和应用 |
| CN111471032B (zh) * | 2019-01-24 | 2023-08-01 | 北京盈科瑞创新药物研究有限公司 | 一种糖苷类衍生物的合成方法及其中间体和应用 |
| CN114585358B (zh) * | 2019-07-26 | 2023-11-10 | 东宝紫星(杭州)生物医药有限公司 | 一种SGLTs/DPP4抑制剂及其应用 |
| CN111269205B (zh) * | 2020-02-19 | 2023-05-26 | 华侨大学 | 一种c-芳基糖苷化合物的制备方法 |
| CN112961196B (zh) * | 2021-02-07 | 2022-05-31 | 中国人民大学 | 一种糖基和多肽修饰的1,2,3-三唑化合物的制备方法 |
| CN115991702B (zh) * | 2021-12-09 | 2024-02-02 | 珠海市藤栢医药有限公司 | 芳基c-葡萄糖苷衍生物、其制备方法及其用途 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PH12000002657B1 (en) * | 1999-10-12 | 2006-02-21 | Bristol Myers Squibb Co | C-aryl glucoside SGLT2 inhibitors |
| US6515117B2 (en) | 1999-10-12 | 2003-02-04 | Bristol-Myers Squibb Company | C-aryl glucoside SGLT2 inhibitors and method |
| US6683056B2 (en) * | 2000-03-30 | 2004-01-27 | Bristol-Myers Squibb Company | O-aryl glucoside SGLT2 inhibitors and method |
| US6936590B2 (en) | 2001-03-13 | 2005-08-30 | Bristol Myers Squibb Company | C-aryl glucoside SGLT2 inhibitors and method |
| JP2004536047A (ja) | 2001-04-11 | 2004-12-02 | ブリストル−マイヤーズ スクイブ カンパニー | 糖尿病処置用ｃ−アリールグルコシドのアミノ酸複合体および方法 |
| CA2512389A1 (en) | 2003-01-03 | 2004-07-29 | Bristol-Myers Squibb Company | Methods of producing c-aryl glucoside sglt2 inhibitors |
| ES2363941T3 (es) * | 2003-03-14 | 2011-08-19 | Astellas Pharma Inc. | Derivados de c-glucósido para el tratamiento de diabetes. |
| ES2649737T5 (es) | 2003-08-01 | 2021-07-07 | Mitsubishi Tanabe Pharma Corp | Compuestos novedosos que tienen actividad inhibidora frente a transportador de glucosa dependiente de sodio |
| CN103030617A (zh) * | 2004-03-16 | 2013-04-10 | 贝林格尔.英格海姆国际有限公司 | 吡喃葡萄糖基取代的苯基衍生物、含该化合物的药物、其用途及其制造方法 |
| JP5238492B2 (ja) * | 2005-04-15 | 2013-07-17 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｓｇｌｔインヒビターとしてのグルコピラノシル置換（ヘテロアリールオキシ−ベンジル）−ベンゼン誘導体 |
| BR112012008924A2 (pt) | 2009-10-20 | 2019-09-24 | Novartis Ag | derivado de glicosídeo e usos do mesmo |
| WO2012025857A1 (en) * | 2010-08-23 | 2012-03-01 | Hetero Research Foundation | Cycloalkyl methoxybenzyl phenyl pyran derivatives as sodium dependent glucose co transporter (sglt2) inhibitors |
| CN102453026A (zh) * | 2010-10-27 | 2012-05-16 | 上海艾力斯医药科技有限公司 | C-芳基葡糖苷衍生物、制备方法及其应用 |
| JP6105489B2 (ja) * | 2011-02-18 | 2017-03-29 | シャンハイ インリ ファーマシューティカル カンパニー リミティド | アリールグルコシド化合物、その調製方法及び使用 |
| US9562029B2 (en) * | 2011-06-25 | 2017-02-07 | Xuanzhu Pharma Co., Ltd. | C-glycoside derivatives |
| CN104059042B (zh) | 2013-03-22 | 2017-02-08 | 正大天晴药业集团股份有限公司 | C-三芳基葡萄糖苷类sglt-2抑制剂 |
| CN105017236A (zh) | 2014-04-14 | 2015-11-04 | 上海迪诺医药科技有限公司 | C-芳基糖苷衍生物、其药物组合物、制备方法及应用 |
| CN105001213B (zh) | 2014-04-14 | 2020-08-28 | 上海迪诺医药科技有限公司 | C-芳基糖苷衍生物、其药物组合物、制备方法及应用 |
-
2014
- 2014-08-11 CN CN201410392098.XA patent/CN105001213B/zh active Active
-
2015
- 2015-04-01 EP EP15780125.9A patent/EP3133071B1/en active Active
- 2015-04-01 JP JP2017505695A patent/JP6577569B2/ja not_active Expired - Fee Related
- 2015-04-01 US US15/304,493 patent/US9914724B2/en not_active Expired - Fee Related
- 2015-04-01 WO PCT/CN2015/075651 patent/WO2015158206A1/zh not_active Ceased
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2017511383A5 (enExample) | ||
| TWI461198B (zh) | 新穎化合物 | |
| JP7662639B2 (ja) | エストロゲン受容体分解活性を有する新規クロマン誘導体およびその使用 | |
| ES2609578T3 (es) | Amino-quinolinas como inhibidores de quinasa | |
| US11918567B2 (en) | Deuterium-enriched pioglitazone | |
| TWI880702B (zh) | 作為nrf2活化劑之羥基吡啶并氧氮呯 | |
| TWI657088B (zh) | 製造稠合雜環化合物之方法 | |
| JP2019137699A (ja) | ２−ヒドロキシ−６−（（２−（１−イソプロピル−１ｈ−ピラゾール−５−イル）ピリジン−３−イル）メトキシ）ベンズアルデヒドの遊離塩基の結晶多形 | |
| JP2015537015A5 (enExample) | ||
| PT2604608E (pt) | Processo para a preparação de metil-{4,6-diamino-2-[1-(2- fluorobenzil)-1h-pirazolo[3,4-b]piridin-3-il]pirimidin-5- il}metilcarbamato e sua purificação para a utilização como princípio ativo farmacêutico | |
| UA128114C2 (uk) | Тверді форми 3-((1r,3r)-1-(2,6-дифтор-4-((1-(3-фторпропіл)азетидин-3-іл)аміно)феніл)-3-метил-1,3,4,9-тетрагідро-2h-піридo[3,4-b]індол-2-іл)-2,2-дифторпропан-1-олу і способи одержання конденсованих трициклічних сполук, що містять заміщене фенільне або піридинільне угруповання, в тому числі способи їх застосування | |
| JP7052798B2 (ja) | アゾールで置換されたピリジン化合物 | |
| CN114394983A (zh) | 多环氨基甲酰基吡啶酮化合物的合成 | |
| US11718611B2 (en) | Benzenesulfonylbenazamide compound for inhibiting BCL-2 protein and composition and use thereof | |
| RU2015118572A (ru) | Получение и составление композиции, содержащей ингибитор мек | |
| AU2018311725A1 (en) | 1,3-di-substituted ketene compound and application thereof | |
| JP2018536031A5 (enExample) | ||
| JP2020500205A5 (enExample) | ||
| CN110156698A (zh) | 2-苯基-1，6-二氢嘧啶-5-甲酸衍生物的制备方法和用途 | |
| CN113365985A (zh) | 一种具有苯并七元环结构的化合物、其制备方法及用途 | |
| RU2639875C2 (ru) | Производное фенила | |
| JP7627747B2 (ja) | 求核芳香族置換によるジオールの不斉化 | |
| JP5664870B2 (ja) | ３環性ベンゾピラン化合物の新規な結晶形態及びその製造方法 | |
| JP2021525784A (ja) | チエノ［２，３−ｃ］ピリダジン−４（１Ｈ）−オン系誘導体及びその使用 | |
| CA3122029A1 (en) | Carborane compounds, carborane analogs, and methods of use thereof |