HRP20230081T1 - Kristalni monohidratni kompleks od 1-cijano-2-(4-ciklopropil-benzil)-4-(beta-d-glukopiranoz-1-il)-benzena i l- prolina u kristalnoj vodi (1:1:1), postupci za njegovu pripravu i njegova uporaba kao sglt inhibitora - Google Patents
Kristalni monohidratni kompleks od 1-cijano-2-(4-ciklopropil-benzil)-4-(beta-d-glukopiranoz-1-il)-benzena i l- prolina u kristalnoj vodi (1:1:1), postupci za njegovu pripravu i njegova uporaba kao sglt inhibitora Download PDFInfo
- Publication number
- HRP20230081T1 HRP20230081T1 HRP20230081TT HRP20230081T HRP20230081T1 HR P20230081 T1 HRP20230081 T1 HR P20230081T1 HR P20230081T T HRP20230081T T HR P20230081TT HR P20230081 T HRP20230081 T HR P20230081T HR P20230081 T1 HRP20230081 T1 HR P20230081T1
- Authority
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- Croatia
- Prior art keywords
- degrees
- crystalline
- diffraction pattern
- complex according
- ray powder
- Prior art date
Links
- 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 title claims 4
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 title claims 4
- 239000013078 crystal Substances 0.000 title claims 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims 2
- 150000004682 monohydrates Chemical class 0.000 title 1
- 229940121377 sodium-glucose co-transporter inhibitor Drugs 0.000 title 1
- 238000000634 powder X-ray diffraction Methods 0.000 claims 9
- 230000005855 radiation Effects 0.000 claims 6
- 102000034534 Cotransporters Human genes 0.000 claims 2
- 108020003264 Cotransporters Proteins 0.000 claims 2
- 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 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 2
- 229940024606 amino acid Drugs 0.000 claims 2
- 150000001413 amino acids Chemical class 0.000 claims 2
- 230000001419 dependent effect Effects 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000008103 glucose Substances 0.000 claims 2
- 230000005764 inhibitory process Effects 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 229910052708 sodium Inorganic materials 0.000 claims 2
- 239000011734 sodium Substances 0.000 claims 2
- 229930182821 L-proline Natural products 0.000 claims 1
- 108091006269 SLC5A2 Proteins 0.000 claims 1
- 102000000070 Sodium-Glucose Transport Proteins Human genes 0.000 claims 1
- 108010080361 Sodium-Glucose Transport Proteins Proteins 0.000 claims 1
- 102000058081 Sodium-Glucose Transporter 2 Human genes 0.000 claims 1
- 238000002441 X-ray diffraction Methods 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- 229960002429 proline Drugs 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H7/00—Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
- C07H7/04—Carbocyclic radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Hematology (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Emergency Medicine (AREA)
- Obesity (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Endocrinology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
- Saccharide Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12177944 | 2012-07-26 | ||
| EP18155079.9A EP3351539B1 (en) | 2012-07-26 | 2013-07-25 | Crystalline monohydrate complex of 1-cyano-2-(4-cyclopropyl-benzyl)-4-(beta-d-glucopyranos-1-yl)-benzene and l-proline in crystal water (1:1:1), methods for its preparation and its use as an sglt inhibitor |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20230081T1 true HRP20230081T1 (hr) | 2023-03-17 |
Family
ID=48874313
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20230081TT HRP20230081T1 (hr) | 2012-07-26 | 2013-07-25 | Kristalni monohidratni kompleks od 1-cijano-2-(4-ciklopropil-benzil)-4-(beta-d-glukopiranoz-1-il)-benzena i l- prolina u kristalnoj vodi (1:1:1), postupci za njegovu pripravu i njegova uporaba kao sglt inhibitora |
| HRP20181972TT HRP20181972T1 (hr) | 2012-07-26 | 2013-07-25 | KRISTALNI KOMPLEKS IZ 1-CIJANO-2-(4-CIKLOPROPIL-BENZIL)-4-(ß-D-GLUKOPIRANOZ-1-IL)-BENZENA, POSTUPCI ZA NJEGOVU PROIZVODNJU I NJEGOVA UPORABA ZA PRIPRAVLJANJE LIJEKOVA |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20181972TT HRP20181972T1 (hr) | 2012-07-26 | 2013-07-25 | KRISTALNI KOMPLEKS IZ 1-CIJANO-2-(4-CIKLOPROPIL-BENZIL)-4-(ß-D-GLUKOPIRANOZ-1-IL)-BENZENA, POSTUPCI ZA NJEGOVU PROIZVODNJU I NJEGOVA UPORABA ZA PRIPRAVLJANJE LIJEKOVA |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US9145434B2 (https=) |
| EP (3) | EP4166548A1 (https=) |
| JP (2) | JP6538556B2 (https=) |
| CN (2) | CN108774200A (https=) |
| AR (1) | AR091908A1 (https=) |
| AU (1) | AU2013294947B2 (https=) |
| BR (1) | BR112015001327B1 (https=) |
| CA (1) | CA2878698C (https=) |
| DK (2) | DK2877460T3 (https=) |
| EA (2) | EA201600506A1 (https=) |
| ES (2) | ES2694675T3 (https=) |
| FI (1) | FI3351539T3 (https=) |
| HR (2) | HRP20230081T1 (https=) |
| HU (1) | HUE061450T2 (https=) |
| LT (1) | LT3351539T (https=) |
| MX (1) | MX357906B (https=) |
| PL (2) | PL2877460T3 (https=) |
| PT (2) | PT2877460T (https=) |
| RS (1) | RS63881B1 (https=) |
| SG (1) | SG11201500574QA (https=) |
| SI (2) | SI2877460T1 (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 |
| DK2981269T3 (da) | 2013-04-04 | 2023-10-23 | Boehringer Ingelheim Vetmedica Gmbh | Behandling af stofskifteforstyrrelser hos hestedyr |
| MX376097B (es) * | 2013-12-17 | 2025-03-07 | Boehringer Ingelheim Vetmedica Gmbh | Inhibidores de sglt2 para usarse en el tratamiento o prevención de trastornos metabólicos en animales felinos. |
| CA2932674C (en) * | 2014-01-23 | 2023-01-24 | Boehringer Ingelheim Vetmedica Gmbh | Treatment of metabolic disorders in canine animals |
| FI3721882T3 (fi) | 2014-04-01 | 2024-09-24 | Boehringer Ingelheim Vetmedica Gmbh | Aineenvaihduntahäiriöiden hoito hevoseläimissä |
| 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 |
| EP4403230A3 (en) | 2014-09-25 | 2025-01-08 | Boehringer Ingelheim Vetmedica GmbH | Combination treatment of sglt2 inhibitors and dopamine agonists for preventing metabolic disorders in equine animals |
| KR20170060035A (ko) * | 2014-09-30 | 2017-05-31 | 지앙수 헨그루이 메디슨 컴퍼니 리미티드 | 나트륨 글루코스 공동운반체 2 억제제의 ｌ- 프롤린 화합물, 및 ｌ- 프롤린 화합물의 모노하이드레이트 및 결정 |
| CZ2015110A3 (cs) * | 2015-02-18 | 2016-08-31 | Zentiva, K.S. | Pevné formy empagliflozinu |
| AU2016310535B2 (en) | 2015-08-27 | 2021-08-19 | Boehringer Ingelheim Vetmedica Gmbh | Liquid pharmaceutical compositions comprising SGLT-2 inhibitors |
| WO2017203457A1 (en) * | 2016-05-26 | 2017-11-30 | Dr. Reddy's Laboratories Limited | Solid state forms of empagliflozin |
| WO2017206827A1 (zh) * | 2016-05-28 | 2017-12-07 | 山东轩竹医药科技有限公司 | 钠-葡萄糖协同转运蛋白2抑制剂的晶型 |
| MX2020006387A (es) | 2017-12-19 | 2020-09-03 | Boehringer Ingelheim Vetmedica Gmbh | Sintesis del cocristal 1:1:1 de 1-ciano-2-(4-ciclopropil-bencil)-4 -(beta-d-glucopiranos-1-il)-benceno, l-prolina y agua. |
| 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 |
| JP7423800B2 (ja) | 2020-02-17 | 2024-01-29 | 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 | ネコにおける心臓疾患の予防および／または治療のためのｓｇｌｔ－２阻害剤の使用 |
| MX2024001184A (es) | 2021-07-28 | 2024-02-27 | Boehringer Ingelheim Vetmedica Gmbh | Uso de inhibidores de sglt-2 para la prevencion y/o tratamiento de cardiopatias en mamiferos no humanos, que excluye felinos, en particular, caninos. |
| CN117715639A (zh) | 2021-07-28 | 2024-03-15 | 勃林格殷格翰动物保健有限公司 | Sglt-2抑制剂用于预防和/或治疗非人哺乳动物中的肾脏病的用途 |
| 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 |
| WO2023227492A1 (en) | 2022-05-25 | 2023-11-30 | Boehringer Ingelheim Vetmedica Gmbh | Aqueous pharmaceutical compositions comprising sglt-2 inhibitors |
| JP2026508912A (ja) | 2023-03-06 | 2026-03-13 | 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 | 液体医薬組成物、特に１種又は複数のｓｇｌｔ－２阻害剤を含む液体医薬組成物の送達のためのシステム |
| AU2024264357A1 (en) | 2023-04-24 | 2025-10-09 | 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 |
| TW202508593A (zh) | 2023-05-24 | 2025-03-01 | 德商百靈佳殷格翰維美迪加股份有限公司 | 包含一或多種sglt-2抑制劑及匹莫苯坦(pimobendan)及/或替米沙坦(telmisartan)之非人類哺乳動物心臟病之組合治療及/或預防 |
| CN121175053A (zh) | 2023-05-24 | 2025-12-19 | 勃林格殷格翰动物保健有限公司 | 包含一或多种sglt-2抑制剂及替米沙坦的非人类哺乳动物中肾脏疾病和/或高血压的组合治疗和/或预防 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002083066A2 (en) | 2001-04-11 | 2002-10-24 | 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 |
| BR0317929A (pt) * | 2003-01-03 | 2006-04-11 | Bristol Myers Squibb Co | métodos de produzir inibidores de sglt2 de glicosìdeo de c-arila |
| ATE557013T1 (de) * | 2004-03-16 | 2012-05-15 | Boehringer Ingelheim Int | Glucopyranosyl-substituierte benzol-derivate, diese verbindungen enthaltende arzneimittel, deren verwendung und verfahren zu ihrer herstellung |
| TW200745075A (en) * | 2005-09-08 | 2007-12-16 | Boehringer Ingelheim Int | Crystalline forms of 1-chloro-4-(β-D-glucopyranos-1-yl)-2-(4-ethynyl-benzyl)-benzene, methods for its preparation and the use thereof for preparing medicaments |
| WO2007093610A1 (en) * | 2006-02-15 | 2007-08-23 | Boehringer Ingelheim International Gmbh | Glucopyranosyl-substituted benzonitrile derivatives, pharmaceutical compositions containing such compounds, their use and process for their manufacture |
| 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 |
| AR065809A1 (es) | 2007-03-22 | 2009-07-01 | Bristol Myers Squibb Co | Formulaciones farmaceuticas que contienen un inhibidor sglt2 |
| CN101754972A (zh) * | 2007-05-18 | 2010-06-23 | 百时美施贵宝公司 | Sglt2抑制剂的晶体结构及其制备方法 |
| CN103319445B (zh) * | 2007-12-27 | 2016-01-20 | 阿斯利康公司 | Sglt2抑制剂的晶体结构及其制备方法 |
| MX2011001855A (es) * | 2008-08-22 | 2011-03-24 | Theracos Inc | Procesos para la preparacion de inhibidores de sglt2. |
| MY155418A (en) | 2008-08-28 | 2015-10-15 | Pfizer | Dioxa-bicyclo[3.2.1]octane-2,3,4-triol derivatives |
| US20100167988A1 (en) | 2008-10-22 | 2010-07-01 | Auspex Pharmaceuticals, 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 |
| DK2981269T3 (da) | 2013-04-04 | 2023-10-23 | Boehringer Ingelheim Vetmedica Gmbh | Behandling af stofskifteforstyrrelser hos hestedyr |
-
2013
- 2013-07-23 US US13/948,751 patent/US9145434B2/en active Active
- 2013-07-25 TW TW102126724A patent/TW201418275A/zh unknown
- 2013-07-25 EP EP22202153.7A patent/EP4166548A1/en active Pending
- 2013-07-25 EP EP18155079.9A patent/EP3351539B1/en active Active
- 2013-07-25 PT PT13740309T patent/PT2877460T/pt unknown
- 2013-07-25 AU AU2013294947A patent/AU2013294947B2/en active Active
- 2013-07-25 ES ES13740309.3T patent/ES2694675T3/es active Active
- 2013-07-25 EA EA201600506A patent/EA201600506A1/ru unknown
- 2013-07-25 WO PCT/EP2013/065736 patent/WO2014016381A1/en not_active Ceased
- 2013-07-25 ES ES18155079T patent/ES2937665T3/es active Active
- 2013-07-25 SI SI201331237T patent/SI2877460T1/sl unknown
- 2013-07-25 PT PT181550799T patent/PT3351539T/pt unknown
- 2013-07-25 SI SI201332031T patent/SI3351539T1/sl unknown
- 2013-07-25 EA EA201500038A patent/EA025438B1/ru not_active IP Right Cessation
- 2013-07-25 SG SG11201500574QA patent/SG11201500574QA/en unknown
- 2013-07-25 CN CN201810468431.9A patent/CN108774200A/zh active Pending
- 2013-07-25 DK DK13740309.3T patent/DK2877460T3/en active
- 2013-07-25 RS RS20230025A patent/RS63881B1/sr unknown
- 2013-07-25 HR HRP20230081TT patent/HRP20230081T1/hr unknown
- 2013-07-25 PL PL13740309T patent/PL2877460T3/pl unknown
- 2013-07-25 AR ARP130102660A patent/AR091908A1/es unknown
- 2013-07-25 HR HRP20181972TT patent/HRP20181972T1/hr unknown
- 2013-07-25 LT LTEP18155079.9T patent/LT3351539T/lt unknown
- 2013-07-25 EP EP13740309.3A patent/EP2877460B1/en active Active
- 2013-07-25 CN CN201380037186.1A patent/CN104470908A/zh active Pending
- 2013-07-25 JP JP2015523552A patent/JP6538556B2/ja active Active
- 2013-07-25 HU HUE18155079A patent/HUE061450T2/hu unknown
- 2013-07-25 PL PL18155079.9T patent/PL3351539T3/pl unknown
- 2013-07-25 DK DK18155079.9T patent/DK3351539T3/da active
- 2013-07-25 BR BR112015001327-9A patent/BR112015001327B1/pt active IP Right Grant
- 2013-07-25 CA CA2878698A patent/CA2878698C/en active Active
- 2013-07-25 MX MX2015000962A patent/MX357906B/es active IP Right Grant
-
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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