CA2895574A1 - Utilisation du 3-carboxy-n-ethyl-n,n-dimethylpropan-1-aminium ou d'un sel pharmaceutiquement acceptable pour le traitement de l'atherosclerose - Google Patents
Utilisation du 3-carboxy-n-ethyl-n,n-dimethylpropan-1-aminium ou d'un sel pharmaceutiquement acceptable pour le traitement de l'atherosclerose Download PDFInfo
- Publication number
- CA2895574A1 CA2895574A1 CA2895574A CA2895574A CA2895574A1 CA 2895574 A1 CA2895574 A1 CA 2895574A1 CA 2895574 A CA2895574 A CA 2895574A CA 2895574 A CA2895574 A CA 2895574A CA 2895574 A1 CA2895574 A1 CA 2895574A1
- Authority
- CA
- Canada
- Prior art keywords
- carboxy
- aminium
- dimethylpropan
- ethyl
- atherosclerosis
- 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.)
- Granted
Links
- 201000001320 Atherosclerosis Diseases 0.000 title claims abstract description 16
- 150000003839 salts Chemical class 0.000 title claims abstract description 12
- ISMYCKWHOZKHNJ-UHFFFAOYSA-O 3-carboxypropyl-ethyl-dimethylazanium Chemical compound CC[N+](C)(C)CCCC(O)=O ISMYCKWHOZKHNJ-UHFFFAOYSA-O 0.000 title claims abstract description 9
- DQSCWIHGBKJVRY-UHFFFAOYSA-N 3-carboxypropyl-ethyl-dimethylazanium;dihydrogen phosphate Chemical compound OP(O)([O-])=O.CC[N+](C)(C)CCCC(O)=O DQSCWIHGBKJVRY-UHFFFAOYSA-N 0.000 claims abstract description 6
- PPDPFXLNXLDRNM-WLHGVMLRSA-N (e)-but-2-enedioate;3-carboxypropyl-ethyl-dimethylazanium;hydron Chemical compound OC(=O)\C=C\C([O-])=O.CC[N+](C)(C)CCCC(O)=O PPDPFXLNXLDRNM-WLHGVMLRSA-N 0.000 claims abstract description 5
- 230000002265 prevention Effects 0.000 claims abstract description 3
- 230000003902 lesion Effects 0.000 description 16
- 230000003143 atherosclerotic effect Effects 0.000 description 15
- 241000699670 Mus sp. Species 0.000 description 8
- 210000000709 aorta Anatomy 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 6
- 239000003651 drinking water Substances 0.000 description 6
- 235000020188 drinking water Nutrition 0.000 description 6
- 230000017531 blood circulation Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-M fumarate(1-) Chemical compound OC(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-M 0.000 description 5
- 230000000879 anti-atherosclerotic effect Effects 0.000 description 4
- 210000001367 artery Anatomy 0.000 description 4
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 4
- JHPNVNIEXXLNTR-UHFFFAOYSA-O 4-(trimethylammonio)butanoic acid Chemical compound C[N+](C)(C)CCCC(O)=O JHPNVNIEXXLNTR-UHFFFAOYSA-O 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 3
- 210000004556 brain Anatomy 0.000 description 3
- 230000034994 death Effects 0.000 description 3
- 231100000517 death Toxicity 0.000 description 3
- 235000005911 diet Nutrition 0.000 description 3
- 230000037213 diet Effects 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- JHPNVNIEXXLNTR-UHFFFAOYSA-N 4-(trimethylammonio)butanoate Chemical compound C[N+](C)(C)CCCC([O-])=O JHPNVNIEXXLNTR-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical group OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004204 blood vessel Anatomy 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 208000010125 myocardial infarction Diseases 0.000 description 2
- 108010071584 oxidized low density lipoprotein Proteins 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical compound C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 description 1
- PHIQHXFUZVPYII-LURJTMIESA-O (S)-carnitinium Chemical compound C[N+](C)(C)C[C@@H](O)CC(O)=O PHIQHXFUZVPYII-LURJTMIESA-O 0.000 description 1
- JHLPIJWOGXXOSI-UHFFFAOYSA-N 2-[ethyl(dimethyl)azaniumyl]butanoate Chemical class C(C)[N+](C)(C)C(C(=O)[O-])CC JHLPIJWOGXXOSI-UHFFFAOYSA-N 0.000 description 1
- GELMWIVBBPAMIO-UHFFFAOYSA-N 2-methylbutan-2-amine Chemical compound CCC(C)(C)N GELMWIVBBPAMIO-UHFFFAOYSA-N 0.000 description 1
- JFWLFLLRLZSBRA-UHFFFAOYSA-N 3-[(trimethylazaniumyl)amino]propanoate;dihydrate Chemical compound O.O.C[N+](C)(C)NCCC([O-])=O JFWLFLLRLZSBRA-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 102100029470 Apolipoprotein E Human genes 0.000 description 1
- 101710095339 Apolipoprotein E Proteins 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 206010014476 Elevated cholesterol Diseases 0.000 description 1
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 1
- 208000035150 Hypercholesterolemia Diseases 0.000 description 1
- 206010022562 Intermittent claudication Diseases 0.000 description 1
- 108010007622 LDL Lipoproteins Proteins 0.000 description 1
- 102000007330 LDL Lipoproteins Human genes 0.000 description 1
- 206010023644 Lacrimation increased Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 206010039424 Salivary hypersecretion Diseases 0.000 description 1
- 208000032023 Signs and Symptoms Diseases 0.000 description 1
- 238000000692 Student's t-test Methods 0.000 description 1
- 210000001744 T-lymphocyte Anatomy 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- 208000032109 Transient ischaemic attack Diseases 0.000 description 1
- 206010054880 Vascular insufficiency Diseases 0.000 description 1
- 206010047139 Vasoconstriction Diseases 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 210000001772 blood platelet Anatomy 0.000 description 1
- 230000036770 blood supply Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000003293 cardioprotective effect Effects 0.000 description 1
- 229960004203 carnitine Drugs 0.000 description 1
- 230000030833 cell death Effects 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 230000006020 chronic inflammation Effects 0.000 description 1
- 208000029078 coronary artery disease Diseases 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007850 degeneration Effects 0.000 description 1
- FIIMLTIASNPROL-UHFFFAOYSA-N dihydrogen phosphate;2-methylbutan-2-ylazanium Chemical compound OP(O)([O-])=O.CCC(C)(C)[NH3+] FIIMLTIASNPROL-UHFFFAOYSA-N 0.000 description 1
- 208000002173 dizziness Diseases 0.000 description 1
- 230000037149 energy metabolism Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 229960002897 heparin Drugs 0.000 description 1
- 229920000669 heparin Polymers 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000001969 hypertrophic effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 208000021156 intermittent vascular claudication Diseases 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 230000000302 ischemic effect Effects 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 230000004317 lacrimation Effects 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 210000002414 leg Anatomy 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000002540 macrophage Anatomy 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 210000000663 muscle cell Anatomy 0.000 description 1
- 230000002107 myocardial effect Effects 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- 230000036407 pain Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000007505 plaque formation Effects 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000010344 pupil dilation Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 208000026451 salivation Diseases 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 201000010875 transient cerebral ischemia Diseases 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 208000023577 vascular insufficiency disease Diseases 0.000 description 1
- 230000025033 vasoconstriction Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Urology & Nephrology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Organic Chemistry (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12198627.7 | 2012-12-20 | ||
| EP12198627 | 2012-12-20 | ||
| PCT/EP2013/077291 WO2014096133A1 (fr) | 2012-12-20 | 2013-12-19 | Utilisation du 3-carboxy-n-éthyl-n,n-diméthylpropan-1-aminium ou d'un sel pharmaceutiquement acceptable pour le traitement de l'athérosclérose |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2895574A1 true CA2895574A1 (fr) | 2014-06-26 |
| CA2895574C CA2895574C (fr) | 2019-11-26 |
Family
ID=47458734
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2895574A Active CA2895574C (fr) | 2012-12-20 | 2013-12-19 | Utilisation du 3-carboxy-n-ethyl-n,n-dimethylpropan-1-aminium ou d'un sel pharmaceutiquement acceptable pour le traitement de l'atherosclerose |
Country Status (11)
| Country | Link |
|---|---|
| CN (1) | CN104869988B (fr) |
| AR (1) | AR094084A1 (fr) |
| BR (1) | BR112015014161B1 (fr) |
| CA (1) | CA2895574C (fr) |
| CU (1) | CU20150067A7 (fr) |
| JO (1) | JO3117B1 (fr) |
| MX (1) | MX362762B (fr) |
| PE (1) | PE20151587A1 (fr) |
| TN (1) | TN2015000236A1 (fr) |
| WO (1) | WO2014096133A1 (fr) |
| ZA (1) | ZA201505093B (fr) |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010149654A1 (fr) * | 2009-06-25 | 2010-12-29 | Grindeks, A Joint Stock Company | Composition pharmaceutique de gamma-butyrobétaïne ou sel pharmaceutiquement acceptable et de meldonium ou sel pharmaceutiquement acceptable |
| JP5706409B2 (ja) * | 2009-06-25 | 2015-04-22 | テトラ，エスイーアー | 新規なサリチル酸塩 |
| LV14345B (lv) * | 2009-10-22 | 2011-07-20 | Grindeks, A/S | 4-[Etil(dimetil)amonija]butanoāts un tā izmantošana kardiovaskulāro slimību ārstēšanai |
| CA2832693C (fr) * | 2011-04-27 | 2018-10-02 | Grindeks, A Joint Stock Company | Utilisation de sels de 3-carboxy-n-ethyl-n,n-dimethylpropan-1-aminium pour traiter une maladie cardiovasculaire |
-
2013
- 2013-12-11 JO JOP/2013/0362A patent/JO3117B1/ar active
- 2013-12-18 AR ARP130104820A patent/AR094084A1/es unknown
- 2013-12-19 WO PCT/EP2013/077291 patent/WO2014096133A1/fr active Application Filing
- 2013-12-19 MX MX2015008138A patent/MX362762B/es active IP Right Grant
- 2013-12-19 CN CN201380066810.0A patent/CN104869988B/zh active Active
- 2013-12-19 PE PE2015000876A patent/PE20151587A1/es not_active Application Discontinuation
- 2013-12-19 BR BR112015014161-7A patent/BR112015014161B1/pt active IP Right Grant
- 2013-12-19 CA CA2895574A patent/CA2895574C/fr active Active
-
2015
- 2015-06-01 TN TNP2015000236A patent/TN2015000236A1/fr unknown
- 2015-06-19 CU CUP2015000067A patent/CU20150067A7/es unknown
- 2015-07-15 ZA ZA2015/05093A patent/ZA201505093B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| TN2015000236A1 (en) | 2016-10-03 |
| CA2895574C (fr) | 2019-11-26 |
| CN104869988B (zh) | 2017-07-28 |
| CU20150067A7 (es) | 2016-01-29 |
| BR112015014161B1 (pt) | 2021-02-17 |
| AR094084A1 (es) | 2015-07-08 |
| MX362762B (es) | 2019-02-06 |
| MX2015008138A (es) | 2016-04-25 |
| JO3117B1 (ar) | 2017-09-20 |
| PE20151587A1 (es) | 2015-12-05 |
| BR112015014161A2 (pt) | 2017-07-11 |
| WO2014096133A1 (fr) | 2014-06-26 |
| ZA201505093B (en) | 2016-04-28 |
| CN104869988A (zh) | 2015-08-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20180824 |