US20140088125A1 - Use of 3-carboxy-n-ethyl-n,n-dimethylpropan-1-aminium salts in the treatment of cardiovascular disease - Google Patents
Use of 3-carboxy-n-ethyl-n,n-dimethylpropan-1-aminium salts in the treatment of cardiovascular disease Download PDFInfo
- Publication number
- US20140088125A1 US20140088125A1 US14/113,709 US201214113709A US2014088125A1 US 20140088125 A1 US20140088125 A1 US 20140088125A1 US 201214113709 A US201214113709 A US 201214113709A US 2014088125 A1 US2014088125 A1 US 2014088125A1
- Authority
- US
- United States
- Prior art keywords
- ethyl
- dimethylpropan
- carboxy
- aminium
- dimethyl
- 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.)
- Abandoned
Links
- 0 C=C1C=C([O-]C=O)NC(=O)N1.CC1=CC=CC=C1[O-]C=O.CC[N+](C)(C)CCCC(=O)O.O=C[O-]/C=C/C(=O)O.O=C[O-]CCC(=O)O.O=P(=O)O[O-].[1*].[HH] Chemical compound C=C1C=C([O-]C=O)NC(=O)N1.CC1=CC=CC=C1[O-]C=O.CC[N+](C)(C)CCCC(=O)O.O=C[O-]/C=C/C(=O)O.O=C[O-]CCC(=O)O.O=P(=O)O[O-].[1*].[HH] 0.000 description 3
- LBZCNMZAHKLETO-FKQPBZCOSA-M C.C=C1C=C([O-]C=O)NC(=O)N1.O=C[O-]/C=C/C(=O)O.O=P(=O)O[O-].[HH] Chemical compound C.C=C1C=C([O-]C=O)NC(=O)N1.O=C[O-]/C=C/C(=O)O.O=P(=O)O[O-].[HH] LBZCNMZAHKLETO-FKQPBZCOSA-M 0.000 description 1
- SCMHXOICFCLBNP-UHFFFAOYSA-O CCOC(=O)CCCBr.CCOC(=O)CCC[N+](C)(C)CC.CC[N+](C)(C)CCCC(=O)O.CC[N+](C)(C)CCCC(=O)[O-].[1*].[1*].[Br-] Chemical compound CCOC(=O)CCCBr.CCOC(=O)CCC[N+](C)(C)CC.CC[N+](C)(C)CCCC(=O)O.CC[N+](C)(C)CCCC(=O)[O-].[1*].[1*].[Br-] SCMHXOICFCLBNP-UHFFFAOYSA-O 0.000 description 1
- DRMIOPJGPNKEQL-UHFFFAOYSA-N CC[N+](C)(C)CCCC(=O)O.O=C1C=C(C(=O)[O-])NC(=O)N1 Chemical compound CC[N+](C)(C)CCCC(=O)O.O=C1C=C(C(=O)[O-])NC(=O)N1 DRMIOPJGPNKEQL-UHFFFAOYSA-N 0.000 description 1
- DQNVYXXUHKSYEB-WLHGVMLRSA-O CC[N+](C)(C)CCCC(=O)O.O=C[O-]/C=C/C(=O)O Chemical compound CC[N+](C)(C)CCCC(=O)O.O=C[O-]/C=C/C(=O)O DQNVYXXUHKSYEB-WLHGVMLRSA-O 0.000 description 1
- NTSDTKJKNGSXOT-UHFFFAOYSA-N CC[N+](C)(C)CCCC(=O)O.O=P(=O)O[O-].[HH] Chemical compound CC[N+](C)(C)CCCC(=O)O.O=P(=O)O[O-].[HH] NTSDTKJKNGSXOT-UHFFFAOYSA-N 0.000 description 1
- ISMYCKWHOZKHNJ-UHFFFAOYSA-O CC[N+](C)(C)CCCC(=O)O.[1*] Chemical compound CC[N+](C)(C)CCCC(=O)O.[1*] ISMYCKWHOZKHNJ-UHFFFAOYSA-O 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D239/08—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms directly attached in position 2
- C07D239/10—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
- C07C229/12—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of acyclic carbon skeletons
-
- 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
-
- 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
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/02—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton
- C07C225/04—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being saturated
- C07C225/06—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being saturated and acyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
- C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
- C07C227/08—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid by reaction of ammonia or amines with acids containing functional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
-
- 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
- C07C55/02—Dicarboxylic acids
- C07C55/10—Succinic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/13—Dicarboxylic acids
- C07C57/15—Fumaric acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/12—Acetic acid esters
- C07C69/14—Acetic acid esters of monohydroxylic compounds
- C07C69/145—Acetic acid esters of monohydroxylic compounds of unsaturated alcohols
- C07C69/157—Acetic acid esters of monohydroxylic compounds of unsaturated alcohols containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/557—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. orotic acid
Definitions
- the present invention relates to new compound 3-carboxy-N-ethyl-N,N-dimethylpropan-1-aminium salts, and to a method of preparation thereof (compound of formula 4)
- the present invention relates also to use of 3-carboxy-N-ethyl-N,N-dimethylpropan-1-aminium salts in the treatment of cardiovascular disease.
- Cardiovascular diseases are a group of disorders of the heart and blood vessels.
- CVD cardiovascular disease
- Myocardial infarction (heart attack) is a serious result of coronary artery disease.
- Myocardial infarction is the irreversible necrosis of heart muscle secondary to prolonged ischemia.
- a heart attack or myocardial infarction is a medical emergency in which the supply of blood to the heart is suddenly and severely reduced or cut off, causing the muscle to die from lack of oxygen.
- More than 1.1 million people experience a heart attack (myocardial infarction) each year, and for many of them, the heart attack is their first symptom of coronary artery disease.
- a heart attack may be severe enough to cause death or it may be silent. As many as one out of every five people have only mild symptoms or none at all, and the heart attack may only be discovered by routine electrocardiography done some time later.
- a heart attack (myocardial infarction) is usually caused by a blood clot that blocks an artery of the heart.
- the artery has often already been narrowed by fatty deposits on its walls. These deposits can tear or break open, reducing the flow of blood and releasing substances that make the platelets of the blood sticky and more likely to form clots.
- ⁇ -Butyrobetaine from which the mammalian organism synthesises carnitine, was primarily characterised as a toxic substance which accelerates respiration, causes salivation and lacrimation, pupil dilation, vasoconstriction and heart stop in diastole LINNEWEH, W. Gamma-Butyrobetain, Crotonbetain und Carnitin im tierischen Stoff Touch. Hoppe-Seylers Zeit intimid für physio strige Chemie. 1929, vol. 181, p. 42-53. At the same time, in later papers other authors ascertained that ⁇ -butyrobetaine is extremely low toxic (LD50>7000 mg/kg, s.c.) ROTZSCH, W. Iber die Toxizitat des Carnitins und utz verwandter Stoffe. Acta biol. med. germ. 1961, vol. 3, p. 28-36.
- 3- (2,2,2-Trimethylhydrazinium) propionate dihydrate is known as compound with cardioprotective properties (this substance being known under its International Nonproprietary Name of Meldonium).
- 3- (2,2,2-Trimethylhydrazinium) propionate is disclosed in U.S. Pat. No. 4,481,218 (INST ORGANICHESKOGO SINTEZA) 06 Nov. 1984 as well in U.S. Pat. no. 4,451,485 A (INSTITU ORCH SINTEZA AKADEMI I) 29 May 1984.
- An object of the present invention is to provide a compound, which has pronounced cardioprotective effect.
- 3-carboxy-N-ethyl-N,N-dimethylpropan-1-aminium salts posses pronounced cardioprotective effect and are more effective as Meldonium dihydrate in vivo myocardial infarction models, due to this property 3-carboxy-N-ethyl-N,N-dimethylpropan-1-aminium salts may be used in medicine.
- 3-Carboxy-N-ethyl-N,N-dimethylpropan-1-aminium salts can be use as a solution for injection.
- the following object of the present invention is a method of preparation of said compound of formula 4.
- Titration assays water content (Fisher) 0.13%, betaine content (HClO 4 ) 93.0%, (E)-butenedioic acid content 46.1%.
- 3-Carboxy-N-ethyl-N,N-dimethylpropan-1-aminium 3-carboxypropanoate was prepared in a form of a water solution.
- ca. 90% 4-[ethyl-(dimethyl)ammonio]butanoate (3) (2.20 g, 12.44 mmol) and succinic acid (1.49 g, 12.62 mmol) were placed in a volumetric flask and dissolved and diluted with water up to 100 ml.
- Rats were adapted to local conditions for two weeks before the start of treatment. Meldonium dihydrate at a dose of 20 mg/kg, gamma-butyrobetaine at a dose of 20 mg/kg and 3-carboxy-N-ethyl-N,N-dimethylpropan-1-aminium salts at dose of 20 mg/kg were administered p.o. daily for 8 weeks. Control rats received water.
- the isolated rat heart experiment was performed essentially as described earlier (Liepinsh et al., J. Cardiovasc. Pharmacol. 2006; 48(6):314-9). Twenty-four hours after the last drug administration hearts were excised and retrogradely perfused via the aorta at a constant pressure with oxygenated Krebs-Henseleit buffer at 37° C. The heart rate, left ventricle end-diastolic pressure and left ventricle developed pressure were continuously recorded. Coronary flow was measured using an ultrasound flow detector (HSE) and the PowerLab 8/30 system from ADInstruments. The hearts were perfused for 20 min to stabilize the hemodynamic functions and then occlusion was performed for 60 min by constricting threads through a plastic tube.
- HSE ultrasound flow detector
- Infarct Size Area of Necrosis/Area at Risk ⁇ 100%.
- the anti-infarction effect of examined substances was investigated in an isolated rat heart infarction model.
- the coronary flow in all experimental groups was decreased for 40% (from 11 ml/min to 7 ml/min).
- the drop of developed left ventricular pressure for 50% was observed.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Cardiology (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (11)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP11163841.7 | 2011-04-27 | ||
EP11163839 | 2011-04-27 | ||
EP11163872 | 2011-04-27 | ||
EP11163839.1 | 2011-04-27 | ||
EP11163841 | 2011-04-27 | ||
EP11163871 | 2011-04-27 | ||
EP11163872.2 | 2011-04-27 | ||
EP11163840 | 2011-04-27 | ||
EP11163840.9 | 2011-04-27 | ||
EP11163871.4 | 2011-04-27 | ||
PCT/EP2012/057806 WO2012146736A1 (en) | 2011-04-27 | 2012-04-27 | Use of 3-carboxy-n-ethyl-n,n-dimethylpropan-1-aminium salts in the treatment of cardiovascular disease |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2012/057806 A-371-Of-International WO2012146736A1 (en) | 2011-04-27 | 2012-04-27 | Use of 3-carboxy-n-ethyl-n,n-dimethylpropan-1-aminium salts in the treatment of cardiovascular disease |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US15/828,660 Continuation US10351534B2 (en) | 2011-04-27 | 2017-12-01 | Use of 3-carboxy-N-ethyl-N,N-dimethylpropan-1-aminium salts in the treatment of cardiovascular disease |
Publications (1)
Publication Number | Publication Date |
---|---|
US20140088125A1 true US20140088125A1 (en) | 2014-03-27 |
Family
ID=46062261
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US14/113,709 Abandoned US20140088125A1 (en) | 2011-04-27 | 2012-04-27 | Use of 3-carboxy-n-ethyl-n,n-dimethylpropan-1-aminium salts in the treatment of cardiovascular disease |
US15/828,660 Active US10351534B2 (en) | 2011-04-27 | 2017-12-01 | Use of 3-carboxy-N-ethyl-N,N-dimethylpropan-1-aminium salts in the treatment of cardiovascular disease |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US15/828,660 Active US10351534B2 (en) | 2011-04-27 | 2017-12-01 | Use of 3-carboxy-N-ethyl-N,N-dimethylpropan-1-aminium salts in the treatment of cardiovascular disease |
Country Status (25)
Country | Link |
---|---|
US (2) | US20140088125A1 (pl) |
EP (1) | EP2702033B1 (pl) |
JP (1) | JP5997762B2 (pl) |
KR (1) | KR20130138827A (pl) |
CN (1) | CN103608326B (pl) |
AU (1) | AU2012247467B2 (pl) |
BR (1) | BR112013027065B1 (pl) |
CA (1) | CA2832693C (pl) |
CY (1) | CY1117890T1 (pl) |
DK (1) | DK2702033T3 (pl) |
EA (1) | EA023547B1 (pl) |
ES (1) | ES2585558T3 (pl) |
GE (1) | GEP20156373B (pl) |
HR (1) | HRP20160998T1 (pl) |
HU (1) | HUE030415T2 (pl) |
IL (1) | IL228891A (pl) |
LT (1) | LT2702033T (pl) |
MX (1) | MX351765B (pl) |
PE (1) | PE20140777A1 (pl) |
PL (1) | PL2702033T3 (pl) |
PT (1) | PT2702033T (pl) |
RS (1) | RS55092B1 (pl) |
SI (1) | SI2702033T1 (pl) |
SM (1) | SMT201600416B (pl) |
WO (1) | WO2012146736A1 (pl) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JO3117B1 (ar) * | 2012-12-20 | 2017-09-20 | Grindeks Jsc | استعمال 3- كربوكسي- ن-إيثيل- ن، ن- ثاني ميثيل بروبان-1– أمينيوم أو ملح منه مقبول صيدلانياً في معالجة تصلب الشرايين |
JO3333B1 (ar) * | 2013-09-26 | 2019-03-13 | Grindeks Jsc | استعمال 3-carboxy-N-ethyl-N,N-dimethylpropan-1-aminium أو ملح مقبول دوائيا منه للوقاية من السكري وعلاجه |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5017611A (en) * | 1987-03-25 | 1991-05-21 | Bremanis Gunar A | Ethyl-3-(2-ethyl-2,2-dimethylhydrazinium)-propionate salts to treat arrhythmia |
WO1997006795A1 (en) * | 1995-08-21 | 1997-02-27 | Ivars Kalvinsh | Pharmaceutical compositions containing gamma-butyrobetain for treatment of blood flow disorders |
EP1103259A1 (de) * | 1999-11-25 | 2001-05-30 | Basf Aktiengesellschaft | Verwendung von y-Butyrobetain Salzen zur Herstellung von Zubereitungen für die menschliche und tierische Ernährung |
WO2009071586A2 (en) * | 2007-12-05 | 2009-06-11 | Grindeks, A Joint Stock Company | 3-(2,2,2-trimethylhydrazinium) propionate salts for treating ischemic heart disease |
Family Cites Families (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1103259A (en) * | 1913-04-23 | 1914-07-14 | John J Buckley | Fly-paper holder. |
GB1238868A (pl) | 1967-08-08 | 1971-07-14 | ||
SU997646A1 (ru) | 1978-11-27 | 1983-02-23 | Ордена Трудового Красного Знамени Институт Органического Синтеза Ан Латвсср | Кормова добавка |
IT1210935B (it) | 1981-09-17 | 1989-09-29 | Inst Orch Sinteza Akademi Nauk | Composizione farmaceutica per il trattamento di malattie cardiovascolari. |
JP3119430B2 (ja) * | 1995-07-25 | 2000-12-18 | 大鵬薬品工業株式会社 | 水酸基ラジカル消去剤 |
LV11728B (en) * | 1995-08-21 | 1997-08-20 | Kalvins Ivars | Pharmaceutical composition |
US5973026A (en) | 1998-02-02 | 1999-10-26 | Xerox Corporation | Ink jet inks |
CA2535150C (en) * | 2003-08-04 | 2010-04-13 | Joint Stock Company "Grindeks" | Non-hygroscopic, stable meldonium salts, method of preparation and pharmaceutical compositions thereof |
CA2508094A1 (en) | 2005-05-20 | 2006-11-20 | Vivier Canada Inc. | Composition for accelerating collagen synthesis |
US7863274B2 (en) | 2005-07-29 | 2011-01-04 | Concert Pharmaceuticals Inc. | Deuterium enriched analogues of tadalafil as PDE5 inhibitors |
LV13705B (en) | 2006-11-06 | 2008-07-20 | Ivars Kalvins | Process for producing high purity intermolecular salt of 3-carboxy-n,n,n-trimethyl-propane-1-amine hydroxide |
JP4761265B2 (ja) | 2007-10-17 | 2011-08-31 | 学校法人甲南学園 | 核酸合成を促進する化合物を含む組成物およびその利用、並びに当該化合物の製造方法 |
ATE527996T1 (de) * | 2007-12-12 | 2011-10-15 | Grindeks Jsc | Medizinische verwendung von 3-(2,2,2- trimethylhydrazinium)propionat-orotat |
WO2010149654A1 (en) * | 2009-06-25 | 2010-12-29 | Grindeks, A Joint Stock Company | Pharmaceutical composition of gamma-butyrobetaine or a pharmaceutically acceptable salt and meldonium or a pharmaceutically acceptable salt |
BRPI1009600A2 (pl) * | 2009-06-25 | 2016-03-22 | Tetra S A | |
LV14345B (lv) * | 2009-10-22 | 2011-07-20 | Grindeks, A/S | 4-[Etil(dimetil)amonija]butanoāts un tā izmantošana kardiovaskulāro slimību ārstēšanai |
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2012
- 2012-04-27 US US14/113,709 patent/US20140088125A1/en not_active Abandoned
- 2012-04-27 BR BR112013027065A patent/BR112013027065B1/pt active IP Right Grant
- 2012-04-27 MX MX2013012551A patent/MX351765B/es active IP Right Grant
- 2012-04-27 LT LTEP12720465.9T patent/LT2702033T/lt unknown
- 2012-04-27 KR KR1020137027933A patent/KR20130138827A/ko not_active Application Discontinuation
- 2012-04-27 EA EA201301080A patent/EA023547B1/ru unknown
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Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5017611A (en) * | 1987-03-25 | 1991-05-21 | Bremanis Gunar A | Ethyl-3-(2-ethyl-2,2-dimethylhydrazinium)-propionate salts to treat arrhythmia |
WO1997006795A1 (en) * | 1995-08-21 | 1997-02-27 | Ivars Kalvinsh | Pharmaceutical compositions containing gamma-butyrobetain for treatment of blood flow disorders |
EP1103259A1 (de) * | 1999-11-25 | 2001-05-30 | Basf Aktiengesellschaft | Verwendung von y-Butyrobetain Salzen zur Herstellung von Zubereitungen für die menschliche und tierische Ernährung |
WO2009071586A2 (en) * | 2007-12-05 | 2009-06-11 | Grindeks, A Joint Stock Company | 3-(2,2,2-trimethylhydrazinium) propionate salts for treating ischemic heart disease |
Non-Patent Citations (1)
Title |
---|
Machine translation of EP 1,103,259 A1 obtained from EPO website (05-2001). * |
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