JP2015522644A5 - - Google Patents
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- Publication number
- JP2015522644A5 JP2015522644A5 JP2015523552A JP2015523552A JP2015522644A5 JP 2015522644 A5 JP2015522644 A5 JP 2015522644A5 JP 2015523552 A JP2015523552 A JP 2015523552A JP 2015523552 A JP2015523552 A JP 2015523552A JP 2015522644 A5 JP2015522644 A5 JP 2015522644A5
- Authority
- JP
- Japan
- Prior art keywords
- crystal
- glucopyranose
- cyclopropyl
- cyano
- benzyl
- 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
- 239000013078 crystal Substances 0.000 claims description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 14
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 11
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- -1 4-cyclopropyl-benzyl Chemical group 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- 229960002429 proline Drugs 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 229930182821 L-proline Natural products 0.000 claims description 5
- 229940024606 amino acid Drugs 0.000 claims description 5
- 150000001413 amino acids Chemical class 0.000 claims description 5
- 230000005855 radiation Effects 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 102100037202 Sodium/myo-inositol cotransporter 2 Human genes 0.000 claims description 4
- 101710090560 Sodium/myo-inositol cotransporter 2 Proteins 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 239000002244 precipitate Substances 0.000 claims description 4
- PESZPPAQWQMZAM-XNBWIAOKSA-N 2-[(4-cyclopropylphenyl)methyl]-4-[(2r,3r,4s,5s,6r)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)oxan-2-yl]benzonitrile Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@]1(O)C1=CC=C(C#N)C(CC=2C=CC(=CC=2)C2CC2)=C1 PESZPPAQWQMZAM-XNBWIAOKSA-N 0.000 claims description 2
- 108091006269 SLC5A2 Proteins 0.000 claims description 2
- 102000000070 Sodium-Glucose Transport Proteins Human genes 0.000 claims description 2
- 108010080361 Sodium-Glucose Transport Proteins Proteins 0.000 claims description 2
- 102000058081 Sodium-Glucose Transporter 2 Human genes 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000002265 prevention Effects 0.000 claims description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- 230000005764 inhibitory process Effects 0.000 claims 1
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12177944 | 2012-07-26 | ||
| EP12177944.1 | 2012-07-26 | ||
| PCT/EP2013/065736 WO2014016381A1 (en) | 2012-07-26 | 2013-07-25 | CRYSTALLINE COMPLEX OF 1-CYANO-2-(4-CYCLOPROPYL-BENZYL)-4-(ß- D-GLUCOPYRANOS-1-YL)-BENZENE, METHODS FOR ITS PREPARATION AND THE USE THEREOF FOR PREPARING MEDICAMENTS |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018089968A Division JP2018135384A (ja) | 2012-07-26 | 2018-05-08 | １−シアノ−２−（４−シクロプロピル−ベンジル）−４−（β−Ｄ−グルコピラノース−１−イル）−ベンゼンの結晶性錯体、その調製方法及び薬物を調製するためのその使用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015522644A JP2015522644A (ja) | 2015-08-06 |
| JP2015522644A5 true JP2015522644A5 (https=) | 2019-05-09 |
| JP6538556B2 JP6538556B2 (ja) | 2019-07-03 |
Family
ID=48874313
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015523552A Active JP6538556B2 (ja) | 2012-07-26 | 2013-07-25 | １−シアノ−２−（４−シクロプロピル−ベンジル）−４−（β−Ｄ−グルコピラノース−１−イル）−ベンゼンの結晶性錯体、その調製方法及び薬物を調製するためのその使用 |
| JP2018089968A Pending JP2018135384A (ja) | 2012-07-26 | 2018-05-08 | １−シアノ−２−（４−シクロプロピル−ベンジル）−４−（β−Ｄ−グルコピラノース−１−イル）−ベンゼンの結晶性錯体、その調製方法及び薬物を調製するためのその使用 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018089968A Pending JP2018135384A (ja) | 2012-07-26 | 2018-05-08 | １−シアノ−２−（４−シクロプロピル−ベンジル）−４−（β−Ｄ−グルコピラノース−１−イル）−ベンゼンの結晶性錯体、その調製方法及び薬物を調製するためのその使用 |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US9145434B2 (https=) |
| EP (3) | EP4166548A1 (https=) |
| JP (2) | JP6538556B2 (https=) |
| CN (2) | CN104470908A (https=) |
| AR (1) | AR091908A1 (https=) |
| AU (1) | AU2013294947B2 (https=) |
| BR (1) | BR112015001327B1 (https=) |
| CA (1) | CA2878698C (https=) |
| DK (2) | DK3351539T3 (https=) |
| EA (2) | EA025438B1 (https=) |
| ES (2) | ES2937665T3 (https=) |
| FI (1) | FI3351539T3 (https=) |
| HR (2) | HRP20181972T1 (https=) |
| HU (1) | HUE061450T2 (https=) |
| LT (1) | LT3351539T (https=) |
| MX (1) | MX357906B (https=) |
| PL (2) | PL3351539T3 (https=) |
| PT (2) | PT3351539T (https=) |
| RS (1) | RS63881B1 (https=) |
| SG (1) | SG11201500574QA (https=) |
| SI (2) | SI3351539T1 (https=) |
| TW (1) | TW201418275A (https=) |
| WO (1) | WO2014016381A1 (https=) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9145434B2 (en) | 2012-07-26 | 2015-09-29 | Boehringer Ingelheim International Gmbh | Crystalline complex of 1-cyano-2-(4-cyclopropyl-benzyl)-4-(ss-d-glucopyranos-1-yl)-benzene, methods for its preparation and the use thereof for preparing medicaments |
| PT2981269T (pt) | 2013-04-04 | 2023-10-10 | Boehringer Ingelheim Vetmedica Gmbh | Tratamento de distúrbios metabólicos em animais equinos |
| ES2969764T3 (es) * | 2013-12-17 | 2024-05-22 | Boehringer Ingelheim Vetmedica Gmbh | Un inhibidor de SGLT-2 para usar en el tratamiento de un trastorno metabólico en animales felinos |
| CN115671290A (zh) | 2014-01-23 | 2023-02-03 | 勃林格殷格翰动物保健有限公司 | 犬科动物中代谢紊乱的治疗 |
| WO2015150299A2 (en) | 2014-04-01 | 2015-10-08 | Boehringer Ingelheim Vetmedica Gmbh | Treatment of metabolic disorders in equine animals |
| CN103965020B (zh) * | 2014-05-06 | 2015-09-09 | 启东东岳药业有限公司 | 制备5-碘-2-溴苄醇的方法 |
| WO2016046150A1 (en) * | 2014-09-25 | 2016-03-31 | Boehringer Ingelheim Vetmedica Gmbh | Combination treatment of sglt2 inhibitors and dopamine agonists for preventing metabolic disorders in equine animals |
| HUE052588T2 (hu) * | 2014-09-30 | 2021-05-28 | Jiangsu Hengrui Medicine Co | Az L-prolin/nátrium-glukóz kotranszporter 2 gátló kristály komplexének kristálya |
| CZ2015110A3 (cs) * | 2015-02-18 | 2016-08-31 | Zentiva, K.S. | Pevné formy empagliflozinu |
| KR102659761B1 (ko) | 2015-08-27 | 2024-04-24 | 베링거잉겔하임베트메디카게엠베하 | Sglt-2 억제제를 포함하는 액상 약제학적 조성물 |
| WO2017203457A1 (en) * | 2016-05-26 | 2017-11-30 | Dr. Reddy's Laboratories Limited | Solid state forms of empagliflozin |
| KR102226465B1 (ko) | 2016-05-28 | 2021-03-11 | 하이난 수안주 파마 코포레이션 리미티드 | 나트륨-글루코스 공수송체 2에 대한 억제제의 결정형 |
| US11225500B2 (en) | 2017-12-19 | 2022-01-18 | Boehringer Ingelheim Vetmedica Gmbh | Synthesis of 1:1:1 co-crystal of 1-cyano-2-(4-cyclopropyl-benzyl)-4-(β-D-glucopyranos-1-yl)-benzene, L-proline and water |
| EP4064854A1 (en) | 2019-11-28 | 2022-10-05 | Boehringer Ingelheim Vetmedica GmbH | Use of sglt-2 inhibitors in the drying-off of non-human mammals |
| AU2021222297B2 (en) | 2020-02-17 | 2026-01-22 | Boehringer Ingelheim Vetmedica Gmbh | Use of SGLT-2 inhibitors for the prevention and/or treatment of cardiac diseases in felines |
| JP2024525981A (ja) | 2021-07-28 | 2024-07-12 | ベーリンガー インゲルハイム フェトメディカ ゲーエムベーハー | ヒト以外の哺乳動物における腎疾患の予防及び／又は治療のためのｓｇｌｔ－２阻害剤の使用 |
| JP2024527434A (ja) | 2021-07-28 | 2024-07-24 | ベーリンガー インゲルハイム フェトメディカ ゲーエムベーハー | ネコ科動物を除く非ヒト哺乳動物、特にイヌ科動物における心臓疾患の予防及び／又は治療のためのｓｇｌｔ－２阻害剤の使用 |
| US20240269105A1 (en) | 2021-07-28 | 2024-08-15 | Boehringer Ingelheim Vetmedica Gmbh | Use of sglt-2 inhibitors for the prevention and/or treatment of hypertension in non-human mammals |
| AU2023277704A1 (en) | 2022-05-25 | 2024-12-05 | Boehringer Ingelheim Vetmedica Gmbh | Aqueous pharmaceutical compositions comprising sglt-2 inhibitors |
| EP4676494A1 (en) | 2023-03-06 | 2026-01-14 | Boehringer Ingelheim Vetmedica GmbH | Systems for delivery of liquid pharmaceutical compositions in particular comprising one or more sglt-2 inhibitor(s) |
| WO2024223388A1 (en) | 2023-04-24 | 2024-10-31 | Boehringer Ingelheim Vetmedica Gmbh | Crystalline complexes between velagliflozin and selected co-crystal forming agents, methods for their preparation and the use thereof for preparing medicaments |
| KR20260019532A (ko) | 2023-05-24 | 2026-02-10 | 베링거잉겔하임베트메디카게엠베하 | 하나 이상의 sglt-2 억제제와 텔미사르탄을 포함하는 비인간 포유류의 신장 질환 및/또는 고혈압의 병용 치료 및/또는 예방 |
| US20240390317A1 (en) | 2023-05-24 | 2024-11-28 | Boehringer Ingelheim Vetmedica Gmbh | Combination treatment and/or prevention of cardiac diseases in non-human mammals comprising one or more sglt-2 inhibitors and pimobendan and/or telmisartan |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2002254567B2 (en) * | 2001-04-11 | 2007-10-11 | Bristol-Myers Squibb Company | Amino acid complexes of C-aryl glucosides for treatment of diabetes and method |
| US7927613B2 (en) * | 2002-02-15 | 2011-04-19 | University Of South Florida | Pharmaceutical co-crystal compositions |
| JP2006516257A (ja) * | 2003-01-03 | 2006-06-29 | ブリストル−マイヤーズ スクイブ カンパニー | Ｃ−アリールグルコシドｓｇｌｔ２阻害剤の製造法 |
| 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 |
| AU2006289093A1 (en) * | 2005-09-08 | 2007-03-15 | Boehringer Ingelheim International Gmbh | Crystalline forms of 1-chloro-4-(beta-D-glucopyranos-1-yl)-2-(4-ethynyl-benzyl)-benzene, methods for its preparation and the use thereof for preparing medicaments |
| AR059489A1 (es) * | 2006-02-15 | 2008-04-09 | Boehringer Ingelheim Vetmed | Derivados de benzonitrilo sustituidos con glucopiranosilo, composiciones farmaceuticas que contienen compuestos de este tipo, su uso y procedimiento para su fabricacion |
| TWI370818B (en) * | 2006-04-05 | 2012-08-21 | Astellas Pharma Inc | Cocrystal of c-glycoside derivative and l-proline |
| PE20080697A1 (es) | 2006-05-03 | 2008-08-05 | Boehringer Ingelheim Int | Derivados de benzonitrilo sustituidos con glucopiranosilo, composiciones farmaceuticas que contienen compuestos de este tipo, su uso y procedimiento para su fabricacion |
| US7919598B2 (en) | 2006-06-28 | 2011-04-05 | Bristol-Myers Squibb Company | Crystal structures of SGLT2 inhibitors and processes for preparing same |
| TW200817424A (en) | 2006-08-04 | 2008-04-16 | Daiichi Sankyo Co Ltd | Benzylphenyl glucopyranoside derivatives |
| TW200904405A (en) | 2007-03-22 | 2009-02-01 | Bristol Myers Squibb Co | Pharmaceutical formulations containing an SGLT2 inhibitor |
| US20080287529A1 (en) * | 2007-05-18 | 2008-11-20 | Bristol-Myers Squibb Company | Crystal structures of sglt2 inhibitors and processes for preparing same |
| CN101468976B (zh) * | 2007-12-27 | 2013-11-20 | 百时美施贵宝公司 | Sglt2抑制剂的晶体结构及其制备方法 |
| CN103910702A (zh) * | 2008-08-22 | 2014-07-09 | 泰拉科斯有限公司 | 制备sglt2抑制剂的方法 |
| AU2009286380B2 (en) | 2008-08-28 | 2011-09-15 | Pfizer Inc. | Dioxa-bicyclo[3.2.1.]octane-2,3,4-triol derivatives |
| WO2010048358A2 (en) | 2008-10-22 | 2010-04-29 | Auspex Pharmaceutical, Inc. | Ethoxyphenylmethyl inhibitors of sglt2 |
| WO2011153712A1 (en) * | 2010-06-12 | 2011-12-15 | Theracos, Inc. | Crystalline form of benzylbenzene sglt2 inhibitor |
| US9145434B2 (en) | 2012-07-26 | 2015-09-29 | Boehringer Ingelheim International Gmbh | Crystalline complex of 1-cyano-2-(4-cyclopropyl-benzyl)-4-(ss-d-glucopyranos-1-yl)-benzene, methods for its preparation and the use thereof for preparing medicaments |
| PT2981269T (pt) | 2013-04-04 | 2023-10-10 | Boehringer Ingelheim Vetmedica Gmbh | Tratamento de distúrbios metabólicos em animais equinos |
-
2013
- 2013-07-23 US US13/948,751 patent/US9145434B2/en active Active
- 2013-07-25 EA EA201500038A patent/EA025438B1/ru not_active IP Right Cessation
- 2013-07-25 EP EP22202153.7A patent/EP4166548A1/en active Pending
- 2013-07-25 AR ARP130102660A patent/AR091908A1/es unknown
- 2013-07-25 EP EP13740309.3A patent/EP2877460B1/en active Active
- 2013-07-25 ES ES18155079T patent/ES2937665T3/es active Active
- 2013-07-25 CA CA2878698A patent/CA2878698C/en active Active
- 2013-07-25 PL PL18155079.9T patent/PL3351539T3/pl unknown
- 2013-07-25 SI SI201332031T patent/SI3351539T1/sl unknown
- 2013-07-25 HR HRP20181972TT patent/HRP20181972T1/hr unknown
- 2013-07-25 CN CN201380037186.1A patent/CN104470908A/zh active Pending
- 2013-07-25 AU AU2013294947A patent/AU2013294947B2/en active Active
- 2013-07-25 JP JP2015523552A patent/JP6538556B2/ja active Active
- 2013-07-25 TW TW102126724A patent/TW201418275A/zh unknown
- 2013-07-25 MX MX2015000962A patent/MX357906B/es active IP Right Grant
- 2013-07-25 WO PCT/EP2013/065736 patent/WO2014016381A1/en not_active Ceased
- 2013-07-25 RS RS20230025A patent/RS63881B1/sr unknown
- 2013-07-25 PT PT181550799T patent/PT3351539T/pt unknown
- 2013-07-25 SI SI201331237T patent/SI2877460T1/sl unknown
- 2013-07-25 EP EP18155079.9A patent/EP3351539B1/en active Active
- 2013-07-25 HR HRP20230081TT patent/HRP20230081T1/hr unknown
- 2013-07-25 PT PT13740309T patent/PT2877460T/pt unknown
- 2013-07-25 DK DK18155079.9T patent/DK3351539T3/da active
- 2013-07-25 CN CN201810468431.9A patent/CN108774200A/zh active Pending
- 2013-07-25 ES ES13740309.3T patent/ES2694675T3/es active Active
- 2013-07-25 BR BR112015001327-9A patent/BR112015001327B1/pt active IP Right Grant
- 2013-07-25 SG SG11201500574QA patent/SG11201500574QA/en unknown
- 2013-07-25 PL PL13740309T patent/PL2877460T3/pl unknown
- 2013-07-25 EA EA201600506A patent/EA201600506A1/ru unknown
- 2013-07-25 LT LTEP18155079.9T patent/LT3351539T/lt unknown
- 2013-07-25 HU HUE18155079A patent/HUE061450T2/hu unknown
- 2013-07-25 DK DK13740309.3T patent/DK2877460T3/en active
-
2018
- 2018-05-08 JP JP2018089968A patent/JP2018135384A/ja active Pending
-
2022
- 2022-07-25 FI FIEP18155079.9T patent/FI3351539T3/fi active
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