ME02175B - L-prolin i ko-kristali limunske kiseline od (2s, 3r, 4r, 5s, 6r)-2-(3- ((5- (4- fluorofenil) tiofen-2-il) metil)-4-metilfenil)-6- (hidroksimetil)tetrahidr0- 2h-piran- 3,4,s-triola - Google Patents
L-prolin i ko-kristali limunske kiseline od (2s, 3r, 4r, 5s, 6r)-2-(3- ((5- (4- fluorofenil) tiofen-2-il) metil)-4-metilfenil)-6- (hidroksimetil)tetrahidr0- 2h-piran- 3,4,s-triolaInfo
- Publication number
- ME02175B ME02175B MEP-2015-109A MEP2015109A ME02175B ME 02175 B ME02175 B ME 02175B ME P2015109 A MEP2015109 A ME P2015109A ME 02175 B ME02175 B ME 02175B
- Authority
- ME
- Montenegro
- Prior art keywords
- proline
- crystal
- citric acid
- tetrahydr0
- thiophen
- Prior art date
Links
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 title claims 15
- 239000013078 crystal Substances 0.000 title claims 13
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 title claims 4
- 229930182821 L-proline Natural products 0.000 title claims 4
- 229960002429 proline Drugs 0.000 title claims 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 title 1
- 230000008018 melting Effects 0.000 claims 2
- 238000002844 melting Methods 0.000 claims 2
- 125000000174 L-prolyl group Chemical class [H]N1C([H])([H])C([H])([H])C([H])([H])[C@@]1([H])C(*)=O 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
- C07C55/22—Tricarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Diabetes (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
- Pyrrole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Claims (8)
1. Ko-kristal L-prolina jedinjenja formule (I-X)
2. Ko-kristal L-prolina kao u Zahtevu 1, pri čemu je ko-kristal u kristalnom obliku.
3. Ko-kristal L-prolina kao u Zahtevu 2, koji sadrži sledeće pXRD pikove °2θ: 3.74, 9.50, 10.98, 17.78, 18.62, 21.94, 23.43 i 26.82.
4. Ko-kristal L-prolina kao u Zahtevu 2, pri čemu, ko-kristal pokazuje tačku topljenja od 188°C, kao što je izmereno pomoću DSC.
5. Ko-kristal limunske kiseline jedinjenja formule (I-X)
6. Ko-kristal limunske kiseline kao u Zahtevu 5, pri čemu je ko-kristal u kristalnom obliku.
7. Ko-kristal limunske kiseline kao u Zahtevu 6, koji sadrži sledeće pXRD pikove °2•: 4,2, 9.16, 12.39, 16.54, 17.69, 19.70, 23.63 and 25.66.
8. Ko-kristal limunske kiseline kao u Zahtevu 6, pri čemu, ko-kristal pokazuje tačku topljenja od oko 156°C, kao što je izmereno pomoću DSC.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161483887P | 2011-05-09 | 2011-05-09 | |
| PCT/US2012/037062 WO2012154812A1 (en) | 2011-05-09 | 2012-05-09 | L-proline and citric acid co-crystals of (2s, 3r, 4r, 5s, 6r )- 2- (3- ((5- (4-fluorophenyl)thiophen-2-yl) methyl) -4-methylphenyl)-6- (hydroxymethyl)tetrahydro-2h-pyran-3,4,5-triol |
| EP12723013.4A EP2707366B1 (en) | 2011-05-09 | 2012-05-09 | L-proline and citric acid co-crystals of (2s, 3r, 4r, 5s, 6r )- 2- (3- ((5- (4-fluorophenyl)thiophen-2-yl) methyl) -4-methylphenyl)-6- (hydroxymethyl)tetrahydro-2h-pyran-3,4,5-triol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ME02175B true ME02175B (me) | 2015-10-20 |
Family
ID=46147741
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MEP-2015-109A ME02175B (me) | 2011-05-09 | 2012-05-09 | L-prolin i ko-kristali limunske kiseline od (2s, 3r, 4r, 5s, 6r)-2-(3- ((5- (4- fluorofenil) tiofen-2-il) metil)-4-metilfenil)-6- (hidroksimetil)tetrahidr0- 2h-piran- 3,4,s-triola |
Country Status (32)
| Country | Link |
|---|---|
| US (1) | US9035044B2 (me) |
| EP (1) | EP2707366B1 (me) |
| JP (1) | JP6106661B2 (me) |
| KR (1) | KR101795514B1 (me) |
| CN (2) | CN103502245B (me) |
| AR (1) | AR086320A1 (me) |
| AU (1) | AU2012253613B2 (me) |
| BR (1) | BR112013028744B1 (me) |
| CA (2) | CA2835704C (me) |
| CL (1) | CL2013003209A1 (me) |
| CY (1) | CY1116550T1 (me) |
| DK (1) | DK2707366T3 (me) |
| EA (1) | EA023496B1 (me) |
| ES (1) | ES2546904T3 (me) |
| HR (1) | HRP20151011T1 (me) |
| HU (1) | HUE027642T2 (me) |
| IL (1) | IL229232A (me) |
| ME (1) | ME02175B (me) |
| MX (1) | MX347178B (me) |
| MY (1) | MY166774A (me) |
| PH (1) | PH12013502274A1 (me) |
| PL (1) | PL2707366T3 (me) |
| PT (1) | PT2707366E (me) |
| RS (1) | RS54205B1 (me) |
| SG (1) | SG194767A1 (me) |
| SI (1) | SI2707366T1 (me) |
| SM (1) | SMT201500194B (me) |
| TW (1) | TWI542596B (me) |
| UA (1) | UA111199C2 (me) |
| UY (1) | UY34061A (me) |
| WO (1) | WO2012154812A1 (me) |
| ZA (1) | ZA201309212B (me) |
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| CN103965267A (zh) * | 2013-01-24 | 2014-08-06 | 江苏豪森医药集团连云港宏创医药有限公司 | 1-(β-D-吡喃葡糖基)-4-甲基-3-[5-(4-氟苯基)-2-噻吩基甲基]苯与L-苯丙氨酸共晶物及其制备方法 |
| US9549909B2 (en) | 2013-05-03 | 2017-01-24 | The Katholieke Universiteit Leuven | Method for the treatment of dravet syndrome |
| BR112015028096B1 (pt) | 2013-05-08 | 2022-04-26 | Lek Pharmaceuticals D.D. | Forma cristalina de um hidrato, processo para a preparação da forma cristalina, composição farmacêutica, uso de forma cristalina e combinação farmacêutica |
| CN103694230B (zh) * | 2013-12-06 | 2016-04-13 | 江苏奥赛康药业股份有限公司 | 一种高纯度卡格列净化合物及其制备方法 |
| CN104693191A (zh) * | 2013-12-09 | 2015-06-10 | 天津药物研究院 | 一种共结晶i及其制备方法和应用 |
| CN103980262B (zh) * | 2014-04-01 | 2016-06-22 | 天津大学 | 卡格列净的b晶型及其结晶制备方法 |
| CN103980261B (zh) * | 2014-04-01 | 2016-06-29 | 天津大学 | 卡格列净的a晶型及其结晶制备方法 |
| EP2933255A1 (en) | 2014-04-17 | 2015-10-21 | LEK Pharmaceuticals d.d. | Novel crystalline form of 1-(beta-D-glucopyranosyl)-4- methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl]benzene |
| US9676741B1 (en) | 2014-06-23 | 2017-06-13 | Sun Pharmaceutical Industries Limited | Co-crystal of dapagliflozin with citric acid |
| EP2990029A1 (en) | 2014-08-29 | 2016-03-02 | Sandoz Ag | Pharmaceutical compositions comprising Canagliflozin |
| CZ2014634A3 (cs) | 2014-09-16 | 2016-03-23 | Zentiva, K.S. | Komplexy canagliflozinu a cyklodextrinů |
| CZ2015435A3 (cs) | 2015-06-25 | 2017-01-04 | Zentiva, K.S. | Pevné formy amorfního canagliflozinu |
| ES2896101T3 (es) | 2015-09-15 | 2022-02-23 | Laurus Labs Ltd | Cocristales de inhibidores de SGLT2, procedimiento para su preparación y composiciones farmacéuticas de los mismos |
| WO2017060924A1 (en) * | 2015-10-09 | 2017-04-13 | Harman Finochem Limited | A novel pipecolic acid co-crystal of canagliflozin and process for the preparation thereof |
| WO2017064679A1 (en) | 2015-10-15 | 2017-04-20 | Lupin Limited | Process for the preparation of amorphous canagliflozin |
| PL3800177T3 (pl) * | 2015-12-22 | 2025-05-19 | Zogenix International Limited | Kompozycje fenfluraminy i sposoby ich wytwarzania |
| CN105503802A (zh) * | 2016-01-15 | 2016-04-20 | 中山大学 | 一种达格列净-柠檬酸共晶的制备方法 |
| EP3468946A4 (en) * | 2016-06-13 | 2020-02-12 | Syneurx International (Taiwan) Corp. | CO CRYSTALS OF LITHIUM BENZOATE AND USES THEREOF |
| MX2018015397A (es) | 2016-06-13 | 2019-08-16 | Syneurx Int Taiwan Corp | Co-cristales de benzoato de sodio y sus usos. |
| CA3226385A1 (en) * | 2018-02-07 | 2019-08-15 | Reata Pharmaceuticals, Inc. | Co-crystal forms of a novobiocin analog and proline |
| WO2020031078A1 (en) * | 2018-08-06 | 2020-02-13 | Hikal Limited | A co-crystal of canagliflozin with alpha-methyl-l-proline and process for the preparation thereof |
| CA3113037A1 (en) * | 2018-09-26 | 2020-04-02 | Lexicon Pharmaceuticals, Inc. | Crystalline forms of n-(1-((2-(dimethylamino)ethyl)amino)-2-methyl-1-oopropan-2-yl)-4-(4-(2-methyl-5-(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(methylthio)tetrahydro-2h-pyran-2-yl)benzyl)phenl)butanamide and methods of their synthesis |
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