WO2005023766A1 - Salt of atorvastatin with metformin - Google Patents
Salt of atorvastatin with metforminDownload PDFInfo
- Publication number
- WO2005023766A1 WO2005023766A1PCT/IN2003/000307IN0300307WWO2005023766A1WO 2005023766 A1WO2005023766 A1WO 2005023766A1IN 0300307 WIN0300307 WIN 0300307WWO 2005023766 A1WO2005023766 A1WO 2005023766A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- formula
- atorvastatin
- compound
- metformin
- salt
- Prior art date
Links
- XUKUURHRXDUEBC-KAYWLYCHSA-NAtorvastatinChemical compoundC=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1XUKUURHRXDUEBC-KAYWLYCHSA-N0.000titleclaimsabstractdescription18
- XUKUURHRXDUEBC-UHFFFAOYSA-NAtorvastatinNatural productsC=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CCC(O)CC(O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1XUKUURHRXDUEBC-UHFFFAOYSA-N0.000titleclaimsabstractdescription18
- 229960005370atorvastatinDrugs0.000titleclaimsabstractdescription18
- XZWYZXLIPXDOLR-UHFFFAOYSA-NmetforminChemical compoundCN(C)C(=N)NC(N)=NXZWYZXLIPXDOLR-UHFFFAOYSA-N0.000titleclaimsabstractdescription18
- 229960003105metforminDrugs0.000titleclaimsabstractdescription17
- 150000003839saltsChemical class0.000titleclaimsabstractdescription11
- 150000001875compoundsChemical class0.000claimsabstractdescription24
- 208000031226HyperlipidaemiaDiseases0.000claimsabstractdescription9
- 201000001421hyperglycemiaDiseases0.000claimsabstract2
- 239000002253acidSubstances0.000claimsdescription6
- 239000012458free baseSubstances0.000claimsdescription4
- 238000000034methodMethods0.000claimsdescription3
- 239000008194pharmaceutical compositionSubstances0.000claims1
- 206010012601diabetes mellitusDiseases0.000description6
- 229940079593drugDrugs0.000description4
- 239000003814drugSubstances0.000description4
- XEKOWRVHYACXOJ-UHFFFAOYSA-NEthyl acetateChemical compoundCCOC(C)=OXEKOWRVHYACXOJ-UHFFFAOYSA-N0.000description3
- IJGRMHOSHXDMSA-UHFFFAOYSA-NAtomic nitrogenChemical compoundN#NIJGRMHOSHXDMSA-UHFFFAOYSA-N0.000description2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-NEthanolChemical compoundCCOLFQSCWFLJHTTHZ-UHFFFAOYSA-N0.000description2
- 229910052751metalInorganic materials0.000description2
- 239000002184metalSubstances0.000description2
- 229940002612prodrugDrugs0.000description2
- 239000000651prodrugSubstances0.000description2
- 239000011541reaction mixtureSubstances0.000description2
- 208000001072type 2 diabetes mellitusDiseases0.000description2
- XUKUURHRXDUEBC-SVBPBHIXSA-N(3s,5s)-7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acidChemical compoundC=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@H](O)C[C@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1XUKUURHRXDUEBC-SVBPBHIXSA-N0.000description1
- QCQCHGYLTSGIGX-GHXANHINSA-N4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acidChemical compoundN([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1QCQCHGYLTSGIGX-GHXANHINSA-N0.000description1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-NDiisopropyl etherChemical compoundCC(C)OC(C)CZAFNJMIOTHYJRJ-UHFFFAOYSA-N0.000description1
- 229940121710HMGCoA reductase inhibitorDrugs0.000description1
- 230000002484anti-cholesterolemic effectEffects0.000description1
- 230000002058anti-hyperglycaemic effectEffects0.000description1
- 239000003472antidiabetic agentSubstances0.000description1
- 239000003524antilipemic agentSubstances0.000description1
- 230000015572biosynthetic processEffects0.000description1
- 159000000007calcium saltsChemical class0.000description1
- 150000001768cationsChemical class0.000description1
- 208000037265diseases, disorders, signs and symptomsDiseases0.000description1
- 208000035475disorderDiseases0.000description1
- 210000002216heartAnatomy0.000description1
- 239000002471hydroxymethylglutaryl coenzyme A reductase inhibitorSubstances0.000description1
- GJRQTCIYDGXPES-UHFFFAOYSA-Niso-butyl acetateNatural productsCC(C)COC(C)=OGJRQTCIYDGXPES-UHFFFAOYSA-N0.000description1
- FGKJLKRYENPLQH-UHFFFAOYSA-MisocaproateChemical compoundCC(C)CCC([O-])=OFGKJLKRYENPLQH-UHFFFAOYSA-M0.000description1
- OQAGVSWESNCJJT-UHFFFAOYSA-Nisovaleric acid methyl esterNatural productsCOC(=O)CC(C)COQAGVSWESNCJJT-UHFFFAOYSA-N0.000description1
- 210000003734kidneyAnatomy0.000description1
- 150000002596lactonesChemical class0.000description1
- 210000004185liverAnatomy0.000description1
- 229910052757nitrogenInorganic materials0.000description1
- 230000000144pharmacologic effectEffects0.000description1
- 210000002784stomachAnatomy0.000description1
Classifications
- 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
- C07D207/30—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 two double bonds between ring members or between ring members and non-ring members
- C07D207/34—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 two 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
- 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
- A61P3/06—Antihyperlipidemics
- 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
- This inventionrelates to a novel compound of formula I, wherein the compound is prodrug and releases two pharmaceutically active moieties, which has independent pharmacological activity and are used for treating hyperlipidemia and diabetes.
- Hyperlipidemiais generally accompanied by other disorders of heart, kidney, stomach or liver. Generally, hyperlipidemia in a patient is accompanied by diabetes. Hyperlipidemia is treated employing a widely known class of drug called statins. Atorvastatin is generally administered as a calcium salt so that active open acid form is made available. Antihyperglycemic agents are used for treatment of diabetes.
- Metforminis used for treatment of Non- insulin dependent diabetes mellitus (NIDDM). Metformin is generally administered a HCI salt.
- NIDDMNon- insulin dependent diabetes mellitus
- the present inventionsdiscloses a novel compound of formula I which can be used for simultaneous treatment of hyperlipidemia and diabetes.
- SUMMARY OF THE INVENTIONThe present invention discloses a novel compound of formula: I. The compound is used for simultaneous treatment of hyperlipidemia and diabetes.
- the compound of formula Iis a prodrug. It is mutual salt of two drugs viz. atorvastatin and metformin. DETAILED DESCRIPTION OF THE INVENTION The present invention discloses a novel compound of formula I, which can be used for treating hyperlipidemia and diabetes simultaneously.
- the important embodiment of the inventionis that the compound of formula I, wherein the two drug molecules form a mutual salt which can be called 'metformin salt of atorvastatin'.
- the inventiondiscloses the compound of formula I, wherein the atorvastatin is an anticholesterolemic or antilipidemic drug and metformin is an antihyperglycemic drug.
- the compound of formula Iis formed when the two compounds are treated with each other under suitable conditions to form a non-covalent bond between the carboxylic group of atorvastatin and nitrogen of metformin.
- the non- covalent bond thus formedis an ionic bond between atorvastatin and metformin.
- the compound of formula Iis a mutual salt of atorvastatin and metformin.
- compound of formula ILike any metal salt of atorvastatin, compound of formula I retain the open chain active form of atorvastatin by preventing undesired inactive lactone formation. Compound of formula I also have the extra advantage of delivering the active open acid form of atorvastatin without employing any metal cation. Unlike prior art, compound of formula I deliver metformin free-base without employing any other acid salt like hydrochloride salt.
- the following non-limiting examplesillustrate the inventors' preferred method for preparing the compound of the invention. EXAMPLES Example 1 To a solution of atorvastatin free acid (10 g, 0.018 mol) in ethyl acetate (200 ml), metformin free base (2.3 g, 0.018 mol) was added and stirred.
- Example 2To a solution of atorvastatin free acid (10 g, 0.018 mol) in isobutyl acetate (200 ml), a solution of metformin free base (2.3 g, 0.018 mol), in ethanol (10 ml) was added and stirred. The reaction mixture was concentrated to about 25 ml and diisopropyl ether (25 ml) was " added to afford the mutual salt of atorvastatin and metformin.
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Diabetes (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hematology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Obesity (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
Abstract
Description
SALT OF ATORVASTATIN WITH METFORMIN FIELD OF THE INVENTION This invention relates to a novel compound of formula I, wherein the compound is prodrug and releases two pharmaceutically active moieties, which has independent pharmacological activity and are used for treating hyperlipidemia and diabetes. BACKGROUND OF THE INVENTION Hyperlipidemia is generally accompanied by other disorders of heart, kidney, stomach or liver. Generally, hyperlipidemia in a patient is accompanied by diabetes. Hyperlipidemia is treated employing a widely known class of drug called statins. Atorvastatin is generally administered as a calcium salt so that active open acid form is made available. Antihyperglycemic agents are used for treatment of diabetes. Metformin is used for treatment of Non- insulin dependent diabetes mellitus (NIDDM). Metformin is generally administered a HCI salt. The present inventions discloses a novel compound of formula I which can be used for simultaneous treatment of hyperlipidemia and diabetes. SUMMARY OF THE INVENTION The present invention discloses a novel compound of formula: I. The compound is used for simultaneous treatment of hyperlipidemia and diabetes.
FORMULA I The compound of formula I is a prodrug. It is mutual salt of two drugs viz. atorvastatin and metformin. DETAILED DESCRIPTION OF THE INVENTION The present invention discloses a novel compound of formula I, which can be used for treating hyperlipidemia and diabetes simultaneously.
FORMULA I The important embodiment of the invention is that the compound of formula I, wherein the two drug molecules form a mutual salt which can be called 'metformin salt of atorvastatin'. The invention discloses the compound of formula I, wherein the atorvastatin is an anticholesterolemic or antilipidemic drug and metformin is an antihyperglycemic drug. The compound of formula I is formed when the two compounds are treated with each other under suitable conditions to form a non-covalent bond between the carboxylic group of atorvastatin and nitrogen of metformin. Preferably, the non- covalent bond thus formed is an ionic bond between atorvastatin and metformin. The compound of formula I is a mutual salt of atorvastatin and metformin. Like any metal salt of atorvastatin, compound of formula I retain the open chain active form of atorvastatin by preventing undesired inactive lactone formation. Compound of formula I also have the extra advantage of delivering the active open acid form of atorvastatin without employing any metal cation. Unlike prior art, compound of formula I deliver metformin free-base without employing any other acid salt like hydrochloride salt. The following non-limiting examples illustrate the inventors' preferred method for preparing the compound of the invention. EXAMPLES Example 1 To a solution of atorvastatin free acid (10 g, 0.018 mol) in ethyl acetate (200 ml), metformin free base (2.3 g, 0.018 mol) was added and stirred. The reaction mixture was concentrated to about 25 ml and chilled to 10° C to afford the mutual salt of atorvastatin and metformin. Example 2 To a solution of atorvastatin free acid (10 g, 0.018 mol) in isobutyl acetate (200 ml), a solution of metformin free base (2.3 g, 0.018 mol), in ethanol (10 ml) was added and stirred. The reaction mixture was concentrated to about 25 ml and diisopropyl ether (25 ml) was"added to afford the mutual salt of atorvastatin and metformin.
Claims
1. A compound of formula I
FORMULA I
2. A compound of formula I as in claim 1, wherein the compound is a mutual salt of atorvastatin and metformin.
3. A process of preparing a compound of formula I comprising of OOstirring atorvastatin free acid with metformin free base
4. A pharmaceutical composition comprising the compound of formula I as in claim 1.
5. A method of treatment of hyperlipidemia and hyperglycemia comprising use of the compound of formula I as in claim 1.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2003269484AAU2003269484A1 (en) | 2003-09-11 | 2003-09-11 | Salt of atorvastatin with metformin |
| PCT/IN2003/000307WO2005023766A1 (en) | 2003-09-11 | 2003-09-11 | Salt of atorvastatin with metformin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/IN2003/000307WO2005023766A1 (en) | 2003-09-11 | 2003-09-11 | Salt of atorvastatin with metformin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2005023766A1true WO2005023766A1 (en) | 2005-03-17 |
Family
ID=34259922
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/IN2003/000307WO2005023766A1 (en) | 2003-09-11 | 2003-09-11 | Salt of atorvastatin with metformin |
Country Status (2)
| Country | Link |
|---|---|
| AU (1) | AU2003269484A1 (en) |
| WO (1) | WO2005023766A1 (en) |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011025271A3 (en)* | 2009-08-25 | 2011-07-14 | 한올바이오파마주식회사 | Metformin ascorbate, method for preparing same, pharmaceutical composition comprising same, and combined formulation comprising same |
| CN102906077A (en)* | 2010-05-26 | 2013-01-30 | 转化技术制药公司 | Combinations of metformin and glucokinase activators and compositions comprising metformin and glucokinase activators |
| WO2014011926A1 (en)* | 2012-07-11 | 2014-01-16 | Elcelyx Therapeutics, Inc. | Compositions comprising statins, biguanides and further agents for reducing cardiometabolic risk |
| US8796338B2 (en) | 2011-01-07 | 2014-08-05 | Elcelyx Therapeutics, Inc | Biguanide compositions and methods of treating metabolic disorders |
| US9050292B2 (en) | 2011-01-07 | 2015-06-09 | Elcelyx Therapeutics, Inc. | Chemosensory receptor ligand-based therapies |
| US9211263B2 (en) | 2012-01-06 | 2015-12-15 | Elcelyx Therapeutics, Inc. | Compositions and methods of treating metabolic disorders |
| US9480663B2 (en) | 2011-01-07 | 2016-11-01 | Elcelyx Therapeutics, Inc. | Biguanide compositions and methods of treating metabolic disorders |
| US9572784B2 (en) | 2011-01-07 | 2017-02-21 | Elcelyx Therapeutics, Inc. | Compositions comprising statins, biguanides and further agents for reducing cardiometabolic risk |
| US10004782B2 (en) | 2012-05-17 | 2018-06-26 | Vtv Therapeutics Llc | Glucokinase activator compositions for the treatment of diabetes |
| US10154972B2 (en) | 2011-01-07 | 2018-12-18 | Elcelyx Therapeutics, Inc. | Biguanide compositions and methods of treating metabolic disorders |
| US10668031B2 (en) | 2011-01-07 | 2020-06-02 | Anji Pharma (Us) Llc | Biguanide compositions and methods of treating metabolic disorders |
| US11759441B2 (en) | 2011-01-07 | 2023-09-19 | Anji Pharmaceuticals Inc. | Biguanide compositions and methods of treating metabolic disorders |
| US11833136B2 (en) | 2018-06-12 | 2023-12-05 | Vtv Therapeutics Llc | Therapeutic uses of glucokinase activators in combination with insulin or insulin analogs |
| US11974971B2 (en) | 2011-01-07 | 2024-05-07 | Anji Pharmaceuticals Inc. | Compositions and methods for treating metabolic disorders |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000045818A1 (en)* | 1999-02-06 | 2000-08-10 | Astrazeneca Ab | Use of 3-hydroxy-3-methylglutaryl coenzym a reductase inhibitors for the manufacture of a medicament for the treatment of diabetic neuropathy |
| WO2003075933A1 (en)* | 2002-03-07 | 2003-09-18 | Upsher-Smith Laboratories, Inc. | Composition for reducing blood glucose and cholesterol |
- 2003
- 2003-09-11WOPCT/IN2003/000307patent/WO2005023766A1/enactiveApplication Filing
- 2003-09-11AUAU2003269484Apatent/AU2003269484A1/ennot_activeAbandoned
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000045818A1 (en)* | 1999-02-06 | 2000-08-10 | Astrazeneca Ab | Use of 3-hydroxy-3-methylglutaryl coenzym a reductase inhibitors for the manufacture of a medicament for the treatment of diabetic neuropathy |
| WO2003075933A1 (en)* | 2002-03-07 | 2003-09-18 | Upsher-Smith Laboratories, Inc. | Composition for reducing blood glucose and cholesterol |
Cited By (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011025271A3 (en)* | 2009-08-25 | 2011-07-14 | 한올바이오파마주식회사 | Metformin ascorbate, method for preparing same, pharmaceutical composition comprising same, and combined formulation comprising same |
| KR101211227B1 (en) | 2009-08-25 | 2012-12-11 | 한올바이오파마주식회사 | Metformin ascorbic acid salt, preparation thereof, pharmaceutical composition comprising the same and combined formulation comprising the same |
| US10363244B2 (en) | 2010-05-26 | 2019-07-30 | Vtv Therapeutics Llc | Compositions comprising metformin and a glucokinase activator |
| US9359313B2 (en) | 2010-05-26 | 2016-06-07 | Vtv Therapeutics Llc | Use of metformin in combination with a glucokinase activator and compositions comprising metformin and a glucokinase activator |
| CN102906077A (en)* | 2010-05-26 | 2013-01-30 | 转化技术制药公司 | Combinations of metformin and glucokinase activators and compositions comprising metformin and glucokinase activators |
| EP2576524A4 (en)* | 2010-05-26 | 2014-03-05 | Transtech Pharma Inc | Use of metformin in combination with a glucokinase activator and compositions comprising metformin and a glucokinase activator |
| US10064846B2 (en) | 2010-05-26 | 2018-09-04 | Vtv Therapeutics Llc | Use of metformin in combination with a glucokinase activator and compositions comprising metformin and a glucokinase activator |
| CN102906077B (en)* | 2010-05-26 | 2015-03-04 | 转化技术制药有限责任公司 | Use of metformin in combination with glucokinase activator and compositions comprising metformin and glucokinase activator |
| US9855251B2 (en) | 2010-05-26 | 2018-01-02 | Vtv Therapeutics Llc | Use of metformin in combination with a glucokinase activator and compositions comprising metformin and a glucokinase activator |
| EP2576524A1 (en)* | 2010-05-26 | 2013-04-10 | TransTech Pharma, Inc | Use of metformin in combination with a glucokinase activator and compositions comprising metformin and a glucokinase activator |
| TWI508723B (en)* | 2010-05-26 | 2015-11-21 | Vtv Therapeutice Llc | Use of metformin in combination with a glucokinase activator and compositions comprising metformin and a glucokinase activator |
| US9962344B2 (en) | 2011-01-07 | 2018-05-08 | Elcelyx Therapeutics, Inc. | Chemosensory receptor ligand-based therapies |
| US10610500B2 (en) | 2011-01-07 | 2020-04-07 | Anji Pharma (Us) Llc | Chemosensory receptor ligand-based therapies |
| US9463170B2 (en) | 2011-01-07 | 2016-10-11 | Elcelyx Therapeutics, Inc. | Chemosensory receptor ligand-based therapies |
| US9481642B2 (en) | 2011-01-07 | 2016-11-01 | Elcelyx Therapeutics, Inc. | Biguanide compositions and methods of treating metabolic disorders |
| US9480663B2 (en) | 2011-01-07 | 2016-11-01 | Elcelyx Therapeutics, Inc. | Biguanide compositions and methods of treating metabolic disorders |
| US9572784B2 (en) | 2011-01-07 | 2017-02-21 | Elcelyx Therapeutics, Inc. | Compositions comprising statins, biguanides and further agents for reducing cardiometabolic risk |
| US11974971B2 (en) | 2011-01-07 | 2024-05-07 | Anji Pharmaceuticals Inc. | Compositions and methods for treating metabolic disorders |
| US11759441B2 (en) | 2011-01-07 | 2023-09-19 | Anji Pharmaceuticals Inc. | Biguanide compositions and methods of treating metabolic disorders |
| US9050292B2 (en) | 2011-01-07 | 2015-06-09 | Elcelyx Therapeutics, Inc. | Chemosensory receptor ligand-based therapies |
| US11065215B2 (en) | 2011-01-07 | 2021-07-20 | Anji Pharma (Us) Llc | Biguanide compositions and methods of treating metabolic disorders |
| US10668031B2 (en) | 2011-01-07 | 2020-06-02 | Anji Pharma (Us) Llc | Biguanide compositions and methods of treating metabolic disorders |
| US10028923B2 (en) | 2011-01-07 | 2018-07-24 | Elcelyx Therapeutics, Inc. | Biguanide compositions and methods of treating metabolic disorders |
| US8796338B2 (en) | 2011-01-07 | 2014-08-05 | Elcelyx Therapeutics, Inc | Biguanide compositions and methods of treating metabolic disorders |
| US10154972B2 (en) | 2011-01-07 | 2018-12-18 | Elcelyx Therapeutics, Inc. | Biguanide compositions and methods of treating metabolic disorders |
| US10159658B2 (en) | 2011-01-07 | 2018-12-25 | Elcelyx Therapeutics, Inc. | Compositions comprising statins, biguanides and further agents for reducing cardiometabolic risk |
| US10201511B2 (en) | 2011-01-07 | 2019-02-12 | Elcelyx Therapeutics, Inc. | Compositions and methods for treating metabolic disorders |
| US10603291B2 (en) | 2012-01-06 | 2020-03-31 | Anji Pharma (Us) Llc | Compositions and methods for treating metabolic disorders |
| US9211263B2 (en) | 2012-01-06 | 2015-12-15 | Elcelyx Therapeutics, Inc. | Compositions and methods of treating metabolic disorders |
| US9770422B2 (en) | 2012-01-06 | 2017-09-26 | Elcelyx Therapeutics, Inc. | Compositions and methods for treating metabolic disorders |
| US10588943B2 (en) | 2012-05-17 | 2020-03-17 | Vtv Therapeutics Llc | Glucokinase activator compositions for the treatment of diabetes |
| US10004782B2 (en) | 2012-05-17 | 2018-06-26 | Vtv Therapeutics Llc | Glucokinase activator compositions for the treatment of diabetes |
| WO2014011926A1 (en)* | 2012-07-11 | 2014-01-16 | Elcelyx Therapeutics, Inc. | Compositions comprising statins, biguanides and further agents for reducing cardiometabolic risk |
| JP2018087214A (en)* | 2012-07-11 | 2018-06-07 | エルセリクス セラピューティクス インコーポレイテッド | Compositions comprising statins, biguanides and further agents for reducing cardiometabolic risk |
| JP2015522080A (en)* | 2012-07-11 | 2015-08-03 | エルセリクス セラピューティクス インコーポレイテッド | Compositions for reducing cardiovascular metabolic risk comprising statins, biguanides, and additional agents |
| US11833136B2 (en) | 2018-06-12 | 2023-12-05 | Vtv Therapeutics Llc | Therapeutic uses of glucokinase activators in combination with insulin or insulin analogs |
| US11974989B2 (en) | 2018-06-12 | 2024-05-07 | Vtv Therapeutics Llc | Therapeutic uses of glucokinase activators in combination with insulin or insulin analogs |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2003269484A1 (en) | 2005-03-29 |
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