WO2014006569A2 - Saxagliptin salts - Google Patents
Saxagliptin salts Download PDFInfo
- Publication number
- WO2014006569A2 WO2014006569A2 PCT/IB2013/055429 IB2013055429W WO2014006569A2 WO 2014006569 A2 WO2014006569 A2 WO 2014006569A2 IB 2013055429 W IB2013055429 W IB 2013055429W WO 2014006569 A2 WO2014006569 A2 WO 2014006569A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- saxagliptin
- acetate
- process according
- bicarbonate
- bisulphate
- Prior art date
Links
- VBTLDAFBDNLTSN-UHFFFAOYSA-O [NH3+]C(CC(C(CC(C1)C2)CC1C1)C21O)C(N(C(C1)C1C1)C1C#N)=O Chemical compound [NH3+]C(CC(C(CC(C1)C2)CC1C1)C21O)C(N(C(C1)C1C1)C1C#N)=O VBTLDAFBDNLTSN-UHFFFAOYSA-O 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
-
- 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
Definitions
- the present invention provides saxagliptin bisulphate, saxagliptin acetate, saxagliptin oxalate, saxagliptin bicarbonate, and saxagliptin carbonate, their polymorphic forms, processes for their preparation, and pharmaceutical compositions thereof.
- Saxagliptin of Formula A an orally-active inhibitor of the dipeptidyl peptidase IV enzyme, chemically designated as (lS,3S,5S)-2-[(2S)-2-Amino-2-(3-hydroxytricyclo [3.3.1.1 3 ' 7 ]dec- l-yl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile, is indicated as an adjunct to diet and exercise to improve glycemic control in adults with type 2 diabetes mellitus.
- U.S. Patent No. 6,395,767 (hereinafter "the '767 patent") provides a process for the preparation of the saxagliptin trifluoroacetate salt.
- the '767 patent also provides the hydrochloride salt of saxagliptin.
- U.S. Patent No. 7,943,656 provides a process for the preparation of crystalline forms of saxagliptin free base, hydrochloride, hydrobromide, hydroiodide, fumarate (2: 1), tartrate, benzoate, trifluoroacetate, ammonium sulfate complex, and nitrate.
- PCT Publication No. WO 2010/1 15974 provides a process for the preparation of anhydrous crystalline forms of saxagliptin hydrochloride.
- PCT Publication No. WO 2012/017028 provides a process for the preparation of crystalline forms of saxagliptin phosphate.
- PCT Publication No. WO 2012/017029 provides a process for the preparation of a crystalline compound comprising a mixture of saxagliptin and an organic C 4 -diacid, wherein the organic C4-diacid is selected from maleic acid, malic acid, L-malic acid, D- malic acid, and succinic acid.
- PCT Publication No. WO 2012/047871 provides a process for the preparation of crystalline Form K, Form Z, Form D, and amorphous saxagliptin hydrochloride.
- Chinese Publication No. CN 102086172 provides a process for the preparation of mesylate, maleate, malate, succinate, and citrate salts of saxagliptin.
- the present inventors have prepared saxagliptin bisulphate, saxagliptin acetate, saxagliptin oxalate, saxagliptin bicarbonate, and saxagliptin carbonate salts.
- the salts of the present invention are easy to prepare and isolate in solid forms, particularly, in crystalline forms. Further, they can be prepared by an efficient, economical, and reproducible process, which is particularly suited to large scale preparation.
- a first aspect of the present invention provides saxagliptin bisulphate.
- a second aspect of the present invention provides a crystalline form of saxagliptin bisulphate.
- a third aspect of the present invention provides saxagliptin acetate.
- a fourth aspect of the present invention provides a crystalline form of saxagliptin acetate.
- a fifth aspect of the present invention provides saxagliptin oxalate.
- a sixth aspect of the present invention provides a crystalline form of saxagliptin oxalate.
- a seventh aspect of the present invention provides a process for the preparation of a compound of Formula I
- HA is selected from sulphuric acid, acetic acid, and oxalic acid.
- An eighth aspect of the present invention provides saxagliptin bicarbonate of Formula II.
- a ninth aspect of the present invention provides a crystalline form of saxagliptin bicarbonate.
- a tenth aspect of the present invention provides a process for the preparation of saxagliptin bicarbonate, which comprises contacting saxagliptin or its salt with a suitable carbonate source.
- An eleventh aspect of the present invention provides saxagliptin carbonate of Formula III.
- a twelfth aspect of the present invention provides a crystalline form of saxagliptin carbonate.
- a thirteenth aspect of the present invention provides a process for the preparation of saxagliptin carbonate, which comprises heating saxagliptin bicarbonate, optionally in the presence of water.
- a fourteenth aspect of the present invention provides the use of saxagliptin salts selected from saxagliptin bisulphate, saxagliptin acetate, saxagliptin oxalate, saxagliptin bicarbonate, or saxagliptin carbonate for the preparation of saxagliptin or salts, solvates, or polymorphs thereof.
- saxagliptin salts selected from saxagliptin bisulphate, saxagliptin acetate, saxagliptin oxalate, saxagliptin bicarbonate, or saxagliptin carbonate for the preparation of saxagliptin or salts, solvates, or polymorphs thereof.
- a fifteenth aspect of the present invention provides a pharmaceutical composition
- saxagliptin salts selected from saxagliptin bisulphate, saxagliptin acetate, saxagliptin oxalate, saxagliptin bicarbonate, or saxagliptin carbonate, and a
- a sixteenth aspect of the present invention provides a method of treating type 2 diabetes mellitus which comprises administering to a patient in need thereof a
- saxagliptin salts selected from saxagliptin bisulphate, saxagliptin acetate, saxagliptin oxalate, saxagliptin bicarbonate, or saxagliptin carbonate, and a pharmaceutically acceptable carrier.
- a first aspect of the present invention provides saxagliptin bisulphate.
- a second aspect of the present invention provides a crystalline form of saxagliptin bisulphate.
- the crystalline form of saxagliptin bisulphate of the present invention may be characterized by an XRPD pattern substantially the same as depicted in Figure 1 , exhibiting interplanar spacing (d) values at about 3.63, 3.39, 3.27, and 3.20 (A), and further exhibiting interplanar spacing (d) values at about 4.22, 3.89, 3.09, 3.05, 2.98, 2.91, 2.79, and 2.63 (A).
- the crystalline form of saxagliptin bisulphate has an XRPD pattern with characteristic peak values (2 ⁇ ) at about 24.50, 26.26, 27.25, and 27.84 ⁇ 0.2°, and additional characteristic peak values (2 ⁇ ) at about 21.04, 22.82, 28.89, 29.26, 29.98, 30.71, 32.05, and 34.06 ⁇ 0.2°.
- the crystalline form of saxagliptin bisulphate of the present invention may be characterized by FTIR as depicted in Figure 2.
- the crystalline form of saxagliptin bisulphate of the present invention may be characterized by DSC as depicted in Figure 3, with a characteristic endothermic peak value at about 100.90°C in the DSC thermogram.
- a third aspect of the present invention provides saxagliptin acetate.
- a fourth aspect of the present invention provides a crystalline form of saxagliptin acetate.
- the crystalline form of saxagliptin acetate of the present invention may be characterized by an XRPD pattern substantially the same as depicted in Figure 4, exhibiting interplanar spacing (d) values at about 1 1.97, 9.84, 5.98, 4.96, and 4.91 (A), and further exhibiting interplanar spacing (d) values substantially at about 6.27, 5.16, 4.71, 4.68, 4.50, 4.45, 3.99, and 3.87 (A).
- the crystalline form of saxagliptin acetate has an XRPD pattern with characteristic peak values (2 ⁇ ) at about 7.38, 8.98, 14.79, 17.85, and 18.03 ⁇ 0.2°, and additional characteristic peak values (2 ⁇ ) at about 14.12, 17.17, 18.82, 18.92, 19.70, 19.94, 22.26, and 22.97 ⁇ 0.2°.
- the crystalline form of saxagliptin acetate of the present invention may be characterized by FTIR as depicted in Figure 5.
- the crystalline form of saxagliptin acetate of the present invention may be characterized by DSC as depicted in Figure 6, with characteristic endothermic peak values at about 68.12, 79.62, 152.38, and 161.14°C in the DSC thermogram.
- a fifth aspect of the present invention provides saxagliptin oxalate.
- a sixth aspect of the present invention provides a crystalline form of saxagliptin oxalate.
- the crystalline form of saxagliptin oxalate of the present invention may be characterized by an XRPD pattern substantially the same as depicted in Figure 7, exhibiting interplanar spacing (d) values substantially at about 12.99, 6.28, 4.96, 4.91, and 4.67 (A), and further exhibiting interplanar spacing (d) values at about 5.99, 5.93, 5.69, 4.59, 4.32, 4.01, and 3.08 (A).
- the crystalline form of saxagliptin oxalate has an XRPD pattern with characteristic peak values (2 ⁇ ) at about 6.80, 14.06, 17.88, 18.06, and 18.98 ⁇ 0.2°, and additional characteristic peak values (2 ⁇ ) at about 14.76, 14.93, 15.56, 19.30, 20.54, 22.15, and 28.97 ⁇ 0.2°.
- the crystalline form of saxagliptin oxalate of the present invention may be characterized by FTIR as depicted in Figure 8.
- the crystalline form of saxagliptin oxalate of the present invention may be characterized by DSC as depicted in Figure 9, with a characteristic endothermic peak value at about 61.67°C, and a characteristic exothermic peak value at about 186.24°C in the DSC thermogram.
- a seventh aspect of the present invention provides a process for the preparation of a compound of Formula I
- HA is selected from sulphuric acid, acetic acid, or oxalic acid.
- the saxagliptin or its salt used as the starting material may be prepared by any of the methods known in the art including those described in, for example, U.S. Patent Nos. 6,395,767, and 7,943,656; PCT Publications WO 2004/052850, WO 2005/1 15982, WO 2005/10601 1, WO 2005/094323, WO 2010/1 15974, WO 2012/017028, WO 2012/017029, and WO 2012/047871.
- saxagliptin or its salt prepared by any of the methods known in the art may be isolated or directly treated with HA.
- saxagliptin or its salt prepared by any of the methods known in the art may be optionally purified prior to treatment with HA to remove foreign particulate matter.
- saxagliptin or its salt may be optionally concentrated to reduce the amount of solvent.
- the saxagliptin salt may optionally be converted to saxagliptin base before treatment with HA.
- Treating saxagliptin or its salt with HA may include adding, dissolving, slurrying, stirring, or a combination thereof. Saxagliptin or its salt may be treated with HA directly, or in the presence of a suitable solvent at a suitable temperature.
- solvent includes any solvent, or a solvent mixture, including for example, water, esters, alkanols, halogenated hydrocarbons, ketones, ethers, polar aprotic solvents, or mixtures thereof.
- esters include ethyl acetate, n-propyl acetate, isopropyl acetate, and n- butyl acetate.
- alkanols include those primary, secondary, and tertiary alcohols having from one to six carbon atoms. Examples of suitable alkanols include methanol, ethanol, n-propanol, isopropanol, and butanol. Examples of halogenated hydrocarbons include dichloromethane, chloroform, and 1 ,2-dichloroethane. Examples of ketones include acetone and methyl ethyl ketone. Examples of ethers include diethyl ether and tetrahydrofuran. Examples of polar aprotic solvents include NN-dimethylformamide, NN-dimethylacetamide, dimethylsulphoxide, acetonitrile, and N-methylpyrrolidone.
- Saxagliptin or its salt is treated with HA at a temperature of from about - 10°C to about 10°C, preferably, from about -5°C to about 5°C.
- the formation of the saxagliptin salt may be accelerated by stirring the reaction mixture for about 10 minutes to about 4 hours at a temperature of from about -5°C to about 40°C, preferably from about 0°C to about 25°C.
- the saxagliptin salt of Formula I may be isolated by filtration, decantation, solvent precipitation, trituration, evaporation, distillation, or combinations thereof.
- An eighth aspect of the present invention provides a saxagliptin bicarbonate of Formula II.
- a ninth aspect of the present invention provides a crystalline form of saxagliptin bicarbonate.
- the crystalline form of saxagliptin bicarbonate of the present invention may be characterized by an XRPD pattern substantially the same as depicted in Figure 10, exhibiting interplanar spacing (d) values at about 3.70, 2.99, and 2.86 (A), and further exhibiting interplanar spacing (d) values at about 7.45, 3.17, 3.12, 2.64, 2.39, and 2.30 (A).
- the crystalline form of saxagliptin bicarbonate has an XRPD pattern with characteristic peak values (2 ⁇ ) at about 24.05, 29.84, and 31.18 ⁇ 0.2°, and additional characteristic peak values (2 ⁇ ) at about 1 1.86, 28.13, 28.60, 33.88, 37.55, and 39.01 ⁇ 0.2°.
- the crystalline form of saxagliptin bicarbonate of the present invention may be characterized by FTIR as depicted in Figure 1 1.
- the crystalline form of saxagliptin bicarbonate of the present invention may be characterized by DSC as depicted in Figure 12, with a characteristic endothermic peak value at about 76.94°C in the DSC thermogram.
- a tenth aspect of the present invention provides a process for the preparation of saxagliptin bicarbonate, which comprises contacting saxagliptin or its salt with a suitable carbonate source.
- saxagliptin or its salt prepared by any of the methods known in the art may be isolated or directly treated with a suitable carbonate source.
- the saxagliptin or its salt prepared by any of the methods known in the art, before treatment with a suitable carbonate source, may be optionally purified to remove foreign particulate matter or treated with activated charcoal to remove coloring and other related impurities in a suitable solvent.
- the solution of saxagliptin or its salt may be optionally concentrated to reduce the amount of solvent.
- the saxagliptin salt may optionally be converted to saxagliptin base before treatment with a suitable carbonate source, optionally in the presence of a base.
- carbonate source includes carbon dioxide gas, dry ice, and carbonic acid prepared in situ by dissolving carbon dioxide gas in water.
- base includes hydroxides, carbonates, and bicarbonates of alkali and alkaline earth metals; ammonia; alkyl amines; hydrazine; and the like.
- hydroxides, carbonates, and bicarbonates of alkali and alkaline earth metals may include lithium hydroxide, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, or potassium bicarbonate.
- alkyl amines may include diethyl amine, triethyl amine, or methyl diethyl amine.
- Treating saxagliptin or its salt with a suitable carbonate source may include adding, dissolving, slurrying, stirring, or combinations thereof. Saxagliptin or its salt may be treated with a suitable carbonate source directly or in the presence of a suitable solvent at a suitable temperature.
- solvent includes any solvent, or a solvent mixture, including for example, water, alkanols, esters, ketones, polar aprotic solvents, or mixtures thereof.
- alkanols include primary, secondary and tertiary alcohols having from one to six carbon atoms.
- suitable alkanols include methanol, ethanol, n-propanol, isopropanol, and butanol.
- esters include ethyl acetate, n-propyl acetate, isopropyl acetate, and n-butyl acetate.
- ketones include acetone and methyl ethyl ketone.
- polar aprotic solvents include NN-dimethylformamide, NN- dimethylacetamide, dimethylsulphoxide, acetonitrile, and N-methylpyrrolidone.
- saxagliptin is treated with dry ice at a temperature of from about 20°C to about 30°C, in ethanol while stirring for about 30 minutes to about 1 hour, preferably, from about 35 minutes to about 45 minutes. Ethanol is removed by distillation under vacuum, followed by the addition of ethyl acetate while stirring. Saxagliptin bicarbonate of Formula II may be isolated by filtration, decantation, solvent precipitation, trituration, evaporation, distillation, or combinations thereof.
- An eleventh aspect of the present invention provides saxagliptin carbonate of Formula III.
- a twelfth aspect of the present invention provides a crystalline form of saxagliptin carbonate.
- the crystalline form of saxagliptin carbonate of the present invention may be characterized by FTIR as depicted in Figure 13.
- the crystalline form of saxagliptin carbonate of the present invention may be characterized by DSC as depicted in Figure 14.
- the crystalline form of saxagliptin carbonate has a characteristic endothermic peak value at about 1 13.45°C in the DSC thermogram.
- a thirteenth aspect of the present invention provides a process for the preparation of saxagliptin carbonate, which comprises heating saxagliptin bicarbonate, optionally in the presence of water.
- saxagliptin bicarbonate is dissolved in water and stirred at a temperature of from about 50°C to about 100°C, preferably, from about 65°C to about 70°C, for about 3 hours to about 6 hours, preferably, for about 4 hours to about 5 hours. Water is then removed by distillation under vacuum. The residue obtained is stirred with ethyl acetate and then removed by distillation under vacuum to obtain the solid. The solid may be washed with ethyl acetate, and is then isolated by filtration, decantation, solvent precipitation, trituration, evaporation, distillation, or combinations thereof to obtain the saxagliptin carbonate.
- a fourteenth aspect of the present invention provides the use of saxagliptin salts selected from saxagliptin bisulphate, saxagliptin acetate, saxagliptin oxalate, saxagliptin bicarbonate, or saxagliptin carbonate for the preparation of saxagliptin or salts, solvates, or polymorphs thereof.
- saxagliptin salts selected from saxagliptin bisulphate, saxagliptin acetate, saxagliptin oxalate, saxagliptin bicarbonate, or saxagliptin carbonate for the preparation of saxagliptin or salts, solvates, or polymorphs thereof.
- Saxagliptin salts may be used for the preparation of saxagliptin by contacting with a base or heating, optionally in the presence of water.
- the base may be selected from the group comprising of hydroxides, carbonates, and bicarbonates of alkali and alkaline earth metals; ammonia; alkyl amines; hydrazine; and the like.
- hydroxides, carbonates, and bicarbonates of alkali and alkaline earth metals include lithium hydroxide, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, or potassium bicarbonate.
- alkyl amines may include diethyl amine, triethyl amine, or methyl diethyl amine. Saxagliptin thus obtained may be converted to salts, solvates, or polymorphs thereof.
- a fifteenth aspect of the present invention provides a pharmaceutical composition
- saxagliptin salts selected from saxagliptin bisulphate, saxagliptin acetate, saxagliptin oxalate, saxagliptin bicarbonate, or saxagliptin carbonate, and a
- a sixteenth aspect of the present invention provides a method of treating type 2 diabetes mellitus which comprises administering to a patient in need thereof a therapeutically effective amount of saxagliptin salts selected from saxagliptin bisulphate, saxagliptin acetate, saxagliptin oxalate, saxagliptin bicarbonate, or saxagliptin carbonate, and a pharmaceutically acceptable carrier.
- saxagliptin salts selected from saxagliptin bisulphate, saxagliptin acetate, saxagliptin oxalate, saxagliptin bicarbonate, or saxagliptin carbonate, and a pharmaceutically acceptable carrier.
- Figure 1 and Figure 1 a depict the X-Ray Powder Diffractogram (XRPD) of saxagliptin bisulphate and the associated values, respectively, prepared as per Example 1.
- XRPD X-Ray Powder Diffractogram
- Figure 2 depicts the Fourier-Transform Infra-red (FTIR) spectrum of saxagliptin bisulphate prepared as per Example 1.
- FTIR Fourier-Transform Infra-red
- FIG. 3 depicts the Differential Scanning Calorimetry (DSC) of saxagliptin bisulphate prepared as per Example 1.
- Figure 4 and Figure 4a depict the XRPD of saxagliptin acetate and the associated values, respectively, prepared as per Example 2.
- Figure 5 depicts the FTIR spectrum of saxagliptin acetate prepared as per Example
- Figure 6 depicts the DSC of saxagliptin acetate prepared as per Example 2.
- Figure 7 and Figure 7a depict the XRPD of saxagliptin oxalate and the associated values, respectively, prepared as per Example 4.
- Figure 8 depicts the FTIR spectrum of saxagliptin oxalate prepared as per Example
- Figure 9 depicts the DSC of saxagliptin oxalate prepared as per Example 4.
- Figure 10 and Figure 10a depict the XRPD of saxagliptin bicarbonate and the associated values, respectively, prepared as per Example 5.
- Figure 1 1 depicts the FTIR spectrum of saxagliptin bicarbonate prepared as per Example 5.
- Figure 12 depicts the DSC of saxagliptin bicarbonate prepared as per Example 5.
- Figure 13 depicts the FTIR spectrum of saxagliptin carbonate prepared as per Example 6.
- Figure 14 depicts the DSC of saxagliptin carbonate prepared as per Example 6.
- the XRPD of the samples were determined by using Instrument: PANalytical; Mode: Expert PRO; Detector: Xcelerator; ScanRange: 3-40; Step size: 0.02; Range: 3-40 degree 2 theta; CuKa radiation at 45kV.
- DSC of the samples was determined by using Instrument: Perkin Elmer, Diamond DSC. Data collection parameters: Scanning rate: 10°C/min; Temperature: 30°C - 300°C.
- a mixture of saxagliptin (1.13 g) and isopropanol (10 mL) was stirred, and cooled to 5°C, followed by the addition of acetic acid (0.22 g) at 5°C to 10°C, and then stirred for 1 hour while gradually raising the temperature to about 20°C to 25°C.
- the reaction mixture was cooled to 0°C to 5°C, and then stirred for 4 hours, maintaining the same temperature, to obtain a white solid.
- the solid was filtered through a sintered funnel under vacuum in a nitrogen environment, washed with isopropanol (10 mL), and dried under vacuum at 40°C to 45°C for 12 hours to 14 hours to obtain the title compound.
- Saxagliptin hydrochloride (5 g) was dissolved in water (50 mL) at 22°C, stirred, and cooled to 1°C in 15 minutes, followed by drop-wise addition of 10% aqueous potassium carbonate solution (20 mL) at 0°C to 5°C over 10 minutes to adjust the pH to 8.3.
- the reaction mixture was stirred for 10 minutes at 5°C and the pH was checked and adjusted to 8.3.
- the water in the reaction mixture was distilled off under vacuum at 25°C in 2 hours, followed by the addition of ethanol (60 mL).
- the inorganic substances in the reaction mixture were filtered under vacuum.
- the inorganic substances were washed with ethanol (15 mL) and filtered to obtain filtrate.
- the obtained filtrates were distilled off under vacuum at 25°C in 1 hour to obtain an oily mass.
- Saxagliptin bicarbonate (300 mg) obtained as per Example 5 was dissolved in water (30 mL) and stirred for 4 hours at 65°C to 70°C.
- the water in the reaction mixture was recovered at 65°C to 70°C under vacuum to obtain a residue.
- ethyl acetate (20 mL) was added, stirred for 10 minutes at 55°C, and the solvent was recovered under vacuum at 50°C to 55°C to obtain a solid mass.
- ethyl acetate (10 mL) was added, and stirred for 15 minutes.
- the solid obtained was filtered, then dried under vacuum at 65°C for 14 hours to obtain the title compound.
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Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP13762566.1A EP2867206A2 (en) | 2012-07-02 | 2013-07-02 | Saxagliptin salts |
SG11201408619WA SG11201408619WA (en) | 2012-07-02 | 2013-07-02 | Saxagliptin salts |
AU2013285078A AU2013285078A1 (en) | 2012-07-02 | 2013-07-02 | Saxagliptin salts |
US14/410,154 US20150329489A1 (en) | 2012-07-02 | 2013-07-02 | Saxagliptin salts |
CA2879824A CA2879824A1 (en) | 2012-07-02 | 2013-07-02 | Saxagliptin salts |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
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IN2061DE2012 | 2012-07-02 | ||
IN2061/DEL/2012 | 2012-07-02 | ||
IN3917/DEL/2012 | 2012-12-19 | ||
IN3917DE2012 | 2012-12-19 |
Publications (2)
Publication Number | Publication Date |
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WO2014006569A2 true WO2014006569A2 (en) | 2014-01-09 |
WO2014006569A3 WO2014006569A3 (en) | 2014-03-06 |
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PCT/IB2013/055429 WO2014006569A2 (en) | 2012-07-02 | 2013-07-02 | Saxagliptin salts |
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EP (1) | EP2867206A2 (en) |
AU (1) | AU2013285078A1 (en) |
CA (1) | CA2879824A1 (en) |
SG (1) | SG11201408619WA (en) |
WO (1) | WO2014006569A2 (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2015166466A1 (en) * | 2014-05-01 | 2015-11-05 | Sun Pharmaceutical Industries Limited | Crystalline form of saxagliptin acetate |
US9994523B2 (en) | 2012-05-24 | 2018-06-12 | Apotex Inc. | Salts of Saxagliptin with organic acids |
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2013
- 2013-07-02 CA CA2879824A patent/CA2879824A1/en not_active Abandoned
- 2013-07-02 WO PCT/IB2013/055429 patent/WO2014006569A2/en active Application Filing
- 2013-07-02 SG SG11201408619WA patent/SG11201408619WA/en unknown
- 2013-07-02 AU AU2013285078A patent/AU2013285078A1/en not_active Abandoned
- 2013-07-02 EP EP13762566.1A patent/EP2867206A2/en not_active Withdrawn
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WO2004052850A2 (en) | 2002-12-09 | 2004-06-24 | Bristol-Myers Squibb Company | Methods and compounds producing dipeptidyl peptidase iv inhibitors and intermediates thereof |
WO2005094323A2 (en) | 2004-03-31 | 2005-10-13 | Bristol-Myers Squibb Company | Process for preparing a dipeptidyl peptidase iv inhibitor and intermediates employed therein |
WO2005106011A2 (en) | 2004-04-14 | 2005-11-10 | Bristol-Myers Squibb Company | Process for preparing dipeptidyl iv inhibitors and intermediates therefor |
WO2005115982A1 (en) | 2004-05-25 | 2005-12-08 | Bristol-Myers Squibb Company | Process for producing a dipeptidyl peptidase iv inhibitor |
US7943656B2 (en) | 2007-04-20 | 2011-05-17 | Bristol-Myers Squibb Company | Crystal forms of saxagliptin and processes for preparing same |
WO2010115974A1 (en) | 2009-04-09 | 2010-10-14 | Sandoz Ag | Crystal forms of saxagliptin |
WO2012017028A1 (en) | 2010-08-06 | 2012-02-09 | Sandoz Ag | A novel crystalline compound comprising saxagliptin and phosphoric acid |
WO2012017029A1 (en) | 2010-08-06 | 2012-02-09 | Sandoz Ag | Novel salts of saxagrliptin with organic di-acids |
WO2012047871A1 (en) | 2010-10-04 | 2012-04-12 | Assia Chemical Industries Ltd | Polymorphs of saxagliptin hydrochloride and processes for preparing them |
CN102086172A (en) | 2011-01-13 | 2011-06-08 | 廖国超 | Medicinal salts of saxagliptin and preparation methods of medicinal salts |
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US9994523B2 (en) | 2012-05-24 | 2018-06-12 | Apotex Inc. | Salts of Saxagliptin with organic acids |
WO2015166466A1 (en) * | 2014-05-01 | 2015-11-05 | Sun Pharmaceutical Industries Limited | Crystalline form of saxagliptin acetate |
Also Published As
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WO2014006569A3 (en) | 2014-03-06 |
CA2879824A1 (en) | 2014-01-09 |
SG11201408619WA (en) | 2015-01-29 |
AU2013285078A1 (en) | 2015-01-29 |
EP2867206A2 (en) | 2015-05-06 |
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