CA1341260C - Compositions pharmaceutiques et/ou dietetiques contenant de la l-carnitine et de la l-lysine - Google Patents
Compositions pharmaceutiques et/ou dietetiques contenant de la l-carnitine et de la l-lysine Download PDFInfo
- Publication number
- CA1341260C CA1341260C CA000607172A CA607172A CA1341260C CA 1341260 C CA1341260 C CA 1341260C CA 000607172 A CA000607172 A CA 000607172A CA 607172 A CA607172 A CA 607172A CA 1341260 C CA1341260 C CA 1341260C
- Authority
- CA
- Canada
- Prior art keywords
- lysine
- carnitine
- composition according
- combination
- hydrochloride
- 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.)
- Expired - Fee Related
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- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 title claims abstract description 106
- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical compound C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 title claims abstract description 85
- 235000005911 diet Nutrition 0.000 title claims abstract description 11
- 230000000378 dietary effect Effects 0.000 title claims abstract description 11
- 229960001518 levocarnitine Drugs 0.000 title 1
- 239000004472 Lysine Substances 0.000 claims abstract description 53
- 235000019766 L-Lysine Nutrition 0.000 claims abstract description 51
- 239000000203 mixture Substances 0.000 claims abstract description 38
- -1 inorganic acid salts Chemical class 0.000 claims abstract description 7
- 230000003387 muscular Effects 0.000 claims abstract description 4
- 150000007524 organic acids Chemical class 0.000 claims abstract description 4
- 229960003646 lysine Drugs 0.000 claims description 52
- 230000000694 effects Effects 0.000 claims description 31
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 18
- BVHLGVCQOALMSV-JEDNCBNOSA-N L-lysine hydrochloride Chemical compound Cl.NCCCC[C@H](N)C(O)=O BVHLGVCQOALMSV-JEDNCBNOSA-N 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- WPLOVIFNBMNBPD-ATHMIXSHSA-N subtilin Chemical compound CC1SCC(NC2=O)C(=O)NC(CC(N)=O)C(=O)NC(C(=O)NC(CCCCN)C(=O)NC(C(C)CC)C(=O)NC(=C)C(=O)NC(CCCCN)C(O)=O)CSC(C)C2NC(=O)C(CC(C)C)NC(=O)C1NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C1NC(=O)C(=C/C)/NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C2NC(=O)CNC(=O)C3CCCN3C(=O)C(NC(=O)C3NC(=O)C(CC(C)C)NC(=O)C(=C)NC(=O)C(CCC(O)=O)NC(=O)C(NC(=O)C(CCCCN)NC(=O)C(N)CC=4C5=CC=CC=C5NC=4)CSC3)C(C)SC2)C(C)C)C(C)SC1)CC1=CC=CC=C1 WPLOVIFNBMNBPD-ATHMIXSHSA-N 0.000 claims description 6
- 229930006000 Sucrose Natural products 0.000 claims description 5
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 5
- 239000005720 sucrose Substances 0.000 claims description 5
- CVHZOJJKTDOEJC-UHFFFAOYSA-M 1,1-dioxo-1,2-benzothiazol-3-olate Chemical compound C1=CC=C2C([O-])=NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-M 0.000 claims description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 4
- 235000005979 Citrus limon Nutrition 0.000 claims description 4
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 4
- 239000005913 Maltodextrin Substances 0.000 claims description 4
- 229920002774 Maltodextrin Polymers 0.000 claims description 4
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 claims description 4
- 229940035034 maltodextrin Drugs 0.000 claims description 4
- 239000007968 orange flavor Substances 0.000 claims description 4
- QEEAPRPFLLJWCF-UHFFFAOYSA-K potassium citrate (anhydrous) Chemical compound [K+].[K+].[K+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QEEAPRPFLLJWCF-UHFFFAOYSA-K 0.000 claims description 4
- 230000003389 potentiating effect Effects 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 239000011780 sodium chloride Substances 0.000 claims description 4
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
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- 239000008103 glucose Substances 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- FZWBNHMXJMCXLU-UHFFFAOYSA-N 2,3,4,5-tetrahydroxy-6-[3,4,5-trihydroxy-6-[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyhexanal Chemical compound OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OCC(O)C(O)C(O)C(O)C=O)O1 FZWBNHMXJMCXLU-UHFFFAOYSA-N 0.000 claims description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 2
- 150000008545 L-lysines Chemical class 0.000 claims description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 2
- 229930195725 Mannitol Natural products 0.000 claims description 2
- 235000010323 ascorbic acid Nutrition 0.000 claims description 2
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- 230000004071 biological effect Effects 0.000 claims description 2
- 229940068682 chewable tablet Drugs 0.000 claims description 2
- 229940119743 dextran 70 Drugs 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
- 239000003978 infusion fluid Substances 0.000 claims description 2
- 235000018977 lysine Nutrition 0.000 claims description 2
- 239000000395 magnesium oxide Substances 0.000 claims description 2
- 239000000594 mannitol Substances 0.000 claims description 2
- 235000010355 mannitol Nutrition 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 claims description 2
- 244000248349 Citrus limon Species 0.000 claims 2
- 239000001508 potassium citrate Substances 0.000 claims 2
- 229960002635 potassium citrate Drugs 0.000 claims 2
- 235000011082 potassium citrates Nutrition 0.000 claims 2
- 239000008213 purified water Substances 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 1
- 230000035622 drinking Effects 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000000796 flavoring agent Substances 0.000 claims 1
- 235000019634 flavors Nutrition 0.000 claims 1
- 235000010234 sodium benzoate Nutrition 0.000 claims 1
- 239000004299 sodium benzoate Substances 0.000 claims 1
- 230000002195 synergetic effect Effects 0.000 abstract description 9
- 206010018429 Glucose tolerance impaired Diseases 0.000 abstract description 3
- 206010019663 Hepatic failure Diseases 0.000 abstract description 3
- 201000005577 familial hyperlipidemia Diseases 0.000 abstract description 3
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- 206010001497 Agitation Diseases 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 230000002232 neuromuscular Effects 0.000 description 9
- 241000700159 Rattus Species 0.000 description 7
- 230000000638 stimulation Effects 0.000 description 7
- 238000005259 measurement Methods 0.000 description 5
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- PHIQHXFUZVPYII-UHFFFAOYSA-N carnitine Chemical compound C[N+](C)(C)CC(O)CC([O-])=O PHIQHXFUZVPYII-UHFFFAOYSA-N 0.000 description 4
- 229960004203 carnitine Drugs 0.000 description 4
- 235000016709 nutrition Nutrition 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 3
- 208000002720 Malnutrition Diseases 0.000 description 3
- RSPISYXLHRIGJD-UHFFFAOYSA-N OOOO Chemical compound OOOO RSPISYXLHRIGJD-UHFFFAOYSA-N 0.000 description 3
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- 206010019280 Heart failures Diseases 0.000 description 2
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- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
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- 229940023486 oral product Drugs 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- PXQPEWDEAKTCGB-UHFFFAOYSA-N orotic acid Chemical compound OC(=O)C1=CC(=O)NC(=O)N1 PXQPEWDEAKTCGB-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 230000002980 postoperative effect Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229940073490 sodium glutamate Drugs 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 238000001356 surgical procedure Methods 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
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 238000002627 tracheal intubation Methods 0.000 description 1
- 210000000689 upper leg Anatomy 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 108700043118 vasectrin II Proteins 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 235000019155 vitamin A Nutrition 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
- A61K31/205—Amine addition salts of organic acids; Inner quaternary ammonium salts, e.g. betaine, carnitine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- 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
-
- 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
- A61P3/02—Nutrients, e.g. vitamins, minerals
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Nutrition Science (AREA)
- Epidemiology (AREA)
- Reproductive Health (AREA)
- Gastroenterology & Hepatology (AREA)
- Urology & Nephrology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8810886 | 1988-08-12 | ||
| FR8810886A FR2635264B1 (fr) | 1988-08-12 | 1988-08-12 | Compositions pharmaceutiques et/ou dietetiques contenant de la l-carnitine et de la l-lysine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1341260C true CA1341260C (fr) | 2001-06-19 |
Family
ID=9369324
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000607172A Expired - Fee Related CA1341260C (fr) | 1988-08-12 | 1989-08-01 | Compositions pharmaceutiques et/ou dietetiques contenant de la l-carnitine et de la l-lysine |
Country Status (10)
| Country | Link |
|---|---|
| EP (2) | EP0354848B1 (enExample) |
| JP (1) | JP2785989B2 (enExample) |
| AT (1) | ATE82122T1 (enExample) |
| CA (1) | CA1341260C (enExample) |
| DE (2) | DE68903448T2 (enExample) |
| ES (1) | ES2043062T3 (enExample) |
| FR (1) | FR2635264B1 (enExample) |
| GR (2) | GR900300149T1 (enExample) |
| PT (1) | PT91430B (enExample) |
| WO (1) | WO1990001316A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2660557B1 (fr) * | 1990-04-09 | 1994-05-27 | Endobio Groupe Etu Rech Risqu | Compositions pharmaceutiques et/ou dietetiques contenant de la carnitine, de la lysine et de la methionine avec ou sans acide pantothenique. |
| US6080788A (en) * | 1997-03-27 | 2000-06-27 | Sole; Michael J. | Composition for improvement of cellular nutrition and mitochondrial energetics |
| IT1306147B1 (it) | 1999-05-28 | 2001-05-30 | Biosalts Srl | Derivati di principi attivi ad attivita' terapeutica e/o nutrizionalee composizioni atte alla somministrazione orale contenenti tali |
| IT1306186B1 (it) | 1999-09-03 | 2001-05-30 | Biosalts Srl | Sali non igroscopici di principi attivi ad attivita' terapeutica e/onutrizionale e composizioni atte alla somministrazione orale |
| IT1317042B1 (it) * | 2000-06-14 | 2003-05-26 | Biosalts Srl | Fumarati doppi di una carnitina e creatina, e integratori alimentari,dietetici e farmaci che li contengono. |
| JP6766044B2 (ja) * | 2015-07-01 | 2020-10-07 | 株式会社明治 | 継粉形成抑制剤 |
| AU2018258250A1 (en) * | 2017-04-25 | 2019-12-12 | Almeda Labs Llc | Amino acid formulations for pancreatic viability |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR4465M (enExample) * | 1965-06-28 | 1966-09-26 | ||
| FR2119882A1 (en) * | 1970-12-31 | 1972-08-11 | Prugnaud Robert | Calcium hypophosphite-ascorbate/carnitine compsn - used as appetite stimulant |
| US3968241A (en) * | 1972-11-06 | 1976-07-06 | Defelice Stephen L | Method of treating cardiac arrhythmias and of improving myocardial contractility and systolic rhythm with carnitive or a pharmaceutically acceptable salt thereof |
| US3830931A (en) * | 1972-11-06 | 1974-08-20 | Felice S De | Carnitine and its use in the treatment of arrhythmia and impaired cardiac function |
| IT1120033B (it) * | 1979-10-05 | 1986-03-19 | Sigma Tau Ind Farmaceuti | Composizione farmaceutica comprendente-carnitina adatta per l'alimentazione parenterale |
| DE3026368A1 (de) * | 1980-07-11 | 1982-02-18 | Lentia GmbH Chem. u. pharm. Erzeugnisse - Industriebedarf, 8000 München | Naehrloesung fuer die vollstaendige parenterale ernaehrung und fuer gesteigerte energieproduktion |
-
1988
- 1988-08-12 FR FR8810886A patent/FR2635264B1/fr not_active Expired - Fee Related
-
1989
- 1989-08-01 CA CA000607172A patent/CA1341260C/fr not_active Expired - Fee Related
- 1989-08-10 EP EP89402257A patent/EP0354848B1/fr not_active Expired - Lifetime
- 1989-08-10 WO PCT/FR1989/000419 patent/WO1990001316A1/fr not_active Ceased
- 1989-08-10 PT PT91430A patent/PT91430B/pt not_active IP Right Cessation
- 1989-08-10 DE DE8989402257T patent/DE68903448T2/de not_active Expired - Fee Related
- 1989-08-10 JP JP1508982A patent/JP2785989B2/ja not_active Expired - Lifetime
- 1989-08-10 ES ES89402257T patent/ES2043062T3/es not_active Expired - Lifetime
- 1989-08-10 EP EP89909580A patent/EP0428608A1/fr active Pending
- 1989-08-10 AT AT89402257T patent/ATE82122T1/de not_active IP Right Cessation
- 1989-08-10 DE DE198989402257T patent/DE354848T1/de active Pending
-
1991
- 1991-09-27 GR GR90300149T patent/GR900300149T1/el unknown
-
1992
- 1992-12-21 GR GR920403006T patent/GR3006598T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE68903448T2 (de) | 1993-03-18 |
| GR900300149T1 (en) | 1991-09-27 |
| JPH04500073A (ja) | 1992-01-09 |
| FR2635264B1 (fr) | 1992-02-28 |
| JP2785989B2 (ja) | 1998-08-13 |
| EP0354848B1 (fr) | 1992-11-11 |
| PT91430A (pt) | 1990-03-08 |
| WO1990001316A1 (fr) | 1990-02-22 |
| ATE82122T1 (de) | 1992-11-15 |
| GR3006598T3 (enExample) | 1993-06-30 |
| DE354848T1 (de) | 1992-05-21 |
| EP0354848A1 (fr) | 1990-02-14 |
| FR2635264A1 (fr) | 1990-02-16 |
| EP0428608A1 (fr) | 1991-05-29 |
| ES2043062T3 (es) | 1993-12-16 |
| DE68903448D1 (de) | 1992-12-17 |
| PT91430B (pt) | 1995-05-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |