IL127266A - Stable, non-hygroscopic mucate salts of l(-) carnitine and alkanoyl l(-) carnitines, a process for their preparation and solid, orally administrable compositions containing such salts - Google Patents
Stable, non-hygroscopic mucate salts of l(-) carnitine and alkanoyl l(-) carnitines, a process for their preparation and solid, orally administrable compositions containing such saltsInfo
- Publication number
- IL127266A IL127266A IL12726697A IL12726697A IL127266A IL 127266 A IL127266 A IL 127266A IL 12726697 A IL12726697 A IL 12726697A IL 12726697 A IL12726697 A IL 12726697A IL 127266 A IL127266 A IL 127266A
- Authority
- IL
- Israel
- Prior art keywords
- salt
- carnitine
- alkanoyl
- salts
- camitine
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 73
- PHIQHXFUZVPYII-UHFFFAOYSA-N carnitine Chemical class C[N+](C)(C)CC(O)CC([O-])=O PHIQHXFUZVPYII-UHFFFAOYSA-N 0.000 title claims description 45
- 239000000203 mixture Substances 0.000 title claims description 22
- 125000001589 carboacyl group Chemical class 0.000 title claims description 20
- 238000000034 method Methods 0.000 title claims description 20
- 230000008569 process Effects 0.000 title claims description 17
- 239000007787 solid Substances 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title description 13
- 125000002252 acyl group Chemical group 0.000 claims abstract description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 239000002002 slurry Substances 0.000 claims description 19
- 239000000047 product Substances 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- -1 isovaleryl Chemical group 0.000 claims description 16
- 239000011541 reaction mixture Substances 0.000 claims description 14
- DSLZVSRJTYRBFB-UHFFFAOYSA-N Galactaric acid Natural products OC(=O)C(O)C(O)C(O)C(O)C(O)=O DSLZVSRJTYRBFB-UHFFFAOYSA-N 0.000 claims description 11
- DSLZVSRJTYRBFB-DUHBMQHGSA-N galactaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O DSLZVSRJTYRBFB-DUHBMQHGSA-N 0.000 claims description 11
- 239000000843 powder Substances 0.000 claims description 8
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 239000003826 tablet Substances 0.000 claims description 8
- 230000018044 dehydration Effects 0.000 claims description 7
- 238000006297 dehydration reaction Methods 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 7
- 238000007711 solidification Methods 0.000 claims description 7
- 230000008023 solidification Effects 0.000 claims description 7
- 239000007910 chewable tablet Substances 0.000 claims description 5
- 235000005911 diet Nutrition 0.000 claims description 5
- 235000015872 dietary supplement Nutrition 0.000 claims description 5
- 235000013305 food Nutrition 0.000 claims description 5
- 239000008187 granular material Substances 0.000 claims description 5
- 239000002775 capsule Substances 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 230000037213 diet Effects 0.000 claims description 3
- 239000002552 dosage form Substances 0.000 claims description 3
- 235000013402 health food Nutrition 0.000 claims description 3
- 235000011837 pasties Nutrition 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 239000006187 pill Substances 0.000 claims description 3
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229940068682 chewable tablet Drugs 0.000 claims description 2
- 238000000227 grinding Methods 0.000 claims description 2
- 239000002417 nutraceutical Substances 0.000 claims description 2
- 235000021436 nutraceutical agent Nutrition 0.000 claims description 2
- 239000008188 pellet Substances 0.000 claims description 2
- 239000007921 spray Substances 0.000 claims description 2
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 2
- 229940023488 pill Drugs 0.000 claims 1
- 239000013589 supplement Substances 0.000 claims 1
- 239000002253 acid Substances 0.000 description 12
- 239000004570 mortar (masonry) Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 238000003860 storage Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 5
- RDHQFKQIGNGIED-MRVPVSSYSA-N O-acetyl-L-carnitine Chemical compound CC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C RDHQFKQIGNGIED-MRVPVSSYSA-N 0.000 description 5
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 5
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 230000000378 dietary effect Effects 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 230000001225 therapeutic effect Effects 0.000 description 5
- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical compound C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 description 4
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 235000016709 nutrition Nutrition 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000006071 cream Substances 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 230000002035 prolonged effect Effects 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- 229940095064 tartrate Drugs 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 2
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 235000001014 amino acid Nutrition 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229960004203 carnitine Drugs 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000002708 enhancing effect Effects 0.000 description 2
- 238000003912 environmental pollution Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000008108 microcrystalline cellulose Substances 0.000 description 2
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 2
- 229940016286 microcrystalline cellulose Drugs 0.000 description 2
- 238000004806 packaging method and process Methods 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- VOTPLFCPIRIALF-UHFFFAOYSA-N 3-(2,4-dioxo-1h-pyrimidine-6-carbonyl)oxy-4-(trimethylazaniumyl)butanoate Chemical compound C[N+](C)(C)CC(CC([O-])=O)OC(=O)C1=CC(=O)NC(=O)N1 VOTPLFCPIRIALF-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 241000777300 Congiopodidae Species 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 101100273207 Dictyostelium discoideum carC gene Proteins 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 235000001453 Glycyrrhiza echinata Nutrition 0.000 description 1
- 244000303040 Glycyrrhiza glabra Species 0.000 description 1
- 235000006200 Glycyrrhiza glabra Nutrition 0.000 description 1
- 235000017382 Glycyrrhiza lepidota Nutrition 0.000 description 1
- 239000001358 L(+)-tartaric acid Substances 0.000 description 1
- 235000011002 L(+)-tartaric acid Nutrition 0.000 description 1
- FEWJPZIEWOKRBE-LWMBPPNESA-N L-(+)-Tartaric acid Natural products OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 208000019914 Mental Fatigue Diseases 0.000 description 1
- 208000024839 Mucopolysaccharidosis type 2, severe form Diseases 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 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 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- GAMPNQJDUFQVQO-UHFFFAOYSA-N acetic acid;phthalic acid Chemical compound CC(O)=O.OC(=O)C1=CC=CC=C1C(O)=O GAMPNQJDUFQVQO-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 229960000678 carnitine chloride Drugs 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 229960000913 crospovidone Drugs 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 235000013681 dietary sucrose Nutrition 0.000 description 1
- 229940008099 dimethicone Drugs 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000006052 feed supplement Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000012041 food component Nutrition 0.000 description 1
- 239000005428 food component Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 229960001518 levocarnitine Drugs 0.000 description 1
- 229940010454 licorice Drugs 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 208000030159 metabolic disease Diseases 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 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
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 239000007967 peppermint flavor Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229940093429 polyethylene glycol 6000 Drugs 0.000 description 1
- 235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 1
- 229920000523 polyvinylpolypyrrolidone Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002243 precursor 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
- 238000004064 recycling Methods 0.000 description 1
- 208000033541 severe form mucopolysaccharidosis type 2 Diseases 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000010891 toxic waste Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 230000036642 wellbeing Effects 0.000 description 1
Classifications
-
- 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
- C07C229/22—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 the carbon skeleton being further substituted by oxygen atoms
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/235—Saturated compounds containing more than one carboxyl group
- C07C59/245—Saturated compounds containing more than one carboxyl group containing hydroxy or O-metal groups
- C07C59/285—Polyhydroxy dicarboxylic acids having five or more carbon atoms, e.g. saccharic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI961116 IT1283086B1 (it) | 1996-05-31 | 1996-05-31 | Sali stabili e non igroscopici di l-carnitina e di alcanoil l-carnitine |
| IT97MI000409A IT1289974B1 (it) | 1997-02-25 | 1997-02-25 | Procedimento per la produzione di sali stabili e non igroscopici di l(-)carnitina e di alcanoli l(-)-carnitine |
| PCT/EP1997/002693 WO1997046512A1 (en) | 1996-05-31 | 1997-05-26 | Stable, non-hygroscopic salts of l(-)carnitine and alkanoyl l(-)carnitines, a process for their preparation and solid, orally administrable compositions containing such salts |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL127266A0 IL127266A0 (en) | 1999-09-22 |
| IL127266A true IL127266A (en) | 2002-09-12 |
Family
ID=26331398
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL12726697A IL127266A (en) | 1996-05-31 | 1997-05-26 | Stable, non-hygroscopic mucate salts of l(-) carnitine and alkanoyl l(-) carnitines, a process for their preparation and solid, orally administrable compositions containing such salts |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US5952379A (el) |
| EP (1) | EP0914315B1 (el) |
| JP (1) | JP4160634B2 (el) |
| CN (1) | CN1177807C (el) |
| AT (1) | ATE200479T1 (el) |
| AU (1) | AU718308B2 (el) |
| BR (1) | BR9709627A (el) |
| CZ (1) | CZ290902B6 (el) |
| DE (1) | DE69704561T2 (el) |
| DK (1) | DK0914315T3 (el) |
| EE (1) | EE03604B1 (el) |
| ES (1) | ES2156381T3 (el) |
| GR (1) | GR3035969T3 (el) |
| HK (1) | HK1024463A1 (el) |
| HU (1) | HU228008B1 (el) |
| IL (1) | IL127266A (el) |
| IS (1) | IS2085B (el) |
| NO (1) | NO323593B1 (el) |
| NZ (1) | NZ333061A (el) |
| PL (1) | PL188558B1 (el) |
| PT (1) | PT914315E (el) |
| SK (1) | SK283105B6 (el) |
| TR (1) | TR199802492T2 (el) |
| WO (1) | WO1997046512A1 (el) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1289974B1 (it) * | 1997-02-25 | 1998-10-19 | Aldo Fassi | Procedimento per la produzione di sali stabili e non igroscopici di l(-)carnitina e di alcanoli l(-)-carnitine |
| IT1312018B1 (it) * | 1999-03-19 | 2002-04-04 | Fassi Aldo | Procedimento migliorato per la produzione di sali non igroscopicidella l(-)-carnitina. |
| ES2322328T3 (es) * | 1999-09-03 | 2009-06-19 | Sigma-Tau Healthscience S.P.A. | L-carnitina ultrafina, procedimientos de preparacion, composiciones que la contienen y procedimiento de uso de la misma. |
| IT1316988B1 (it) | 2000-02-10 | 2003-05-26 | Sigma Tau Ind Farmaceuti | Procedimento migliorato di preparazione industriale di mucati dellal-carnitina e di alcanoil l-carnitine. |
| US8252309B2 (en) * | 2000-04-04 | 2012-08-28 | Sigma-Tau Industrie Farmaceutiche Riunite Spa | Dietary supplement energy-providing to skeletal muscles |
| ITRM20010030A1 (it) * | 2001-01-23 | 2002-07-23 | Aldo Fassi | Sali di carnitine utili come integratori dietetici/nutrizionali o come farmaci, composizioni che li contengono e procedimenti per la loro pr |
| ITRM20010029A1 (it) * | 2001-01-23 | 2002-07-23 | Aldo Fassi | Sali metallici di carnitine utili come integratori dietetici/nutrizionali o come farmaci, composizioni che li contengono e procedimenti per |
| ITRM20010044A1 (it) * | 2001-01-29 | 2002-07-29 | Sigma Tau Healthscience Spa | Integratore alimentare ad effetto dimagrante. |
| DE10133200A1 (de) * | 2001-07-07 | 2003-01-23 | Beiersdorf Ag | Carnitin enthaltende kosmetische und dermatologische Zubereitungen zur Behandlung und aktiven Prävention trockener Haut und anderer negativer Veränderungen der physiologischen Homöostase der gesunden Haut |
| ITRM20020055A1 (it) * | 2002-02-04 | 2003-08-04 | Aldo Fassi | Sali metallici di carnitine, integratori dietetici/nutritivi che li contengono e kit dietetici per contrastare disturbi sessuali in soggetti |
| JP2006111550A (ja) * | 2004-10-13 | 2006-04-27 | Nisshin Pharma Inc | カルニチン含有製品 |
| CN101212956A (zh) * | 2005-07-05 | 2008-07-02 | 隆萨股份公司 | 生产干肉碱粉末或颗粒的喷雾干燥法 |
| CN101209975B (zh) | 2006-12-29 | 2010-12-01 | 沈阳科硕营养科技有限公司 | 左旋肉碱富马酸钙及其制备方法与用途 |
| EP2425834A1 (en) * | 2010-09-06 | 2012-03-07 | Lonza Ltd. | Process for the production of l-carnitine tartrate |
| CN102911067A (zh) * | 2011-08-04 | 2013-02-06 | 广州市奥海生物科技有限公司 | 左旋肉碱丙酮酸盐及其制备方法与用途 |
| CN102911068A (zh) * | 2011-08-04 | 2013-02-06 | 广州市奥海生物科技有限公司 | 左旋肉碱l-苹果酸盐及其制备方法与用途 |
| JP6393310B2 (ja) * | 2013-04-26 | 2018-09-19 | サノフイＳａｎｏｆｉ | ５−クロロ−チオフェン−２−カルボン酸［（ｓ）−２−［メチル−３−（２−オキソ−ピロリジン−１−イル）−ベンゼンスルホニルアミノ］−３−（４−メチル−ピペラジン−１−イル）−３−オキソ−プロプリル］アミドの酒石酸塩 |
| CN103664667A (zh) * | 2013-12-16 | 2014-03-26 | 天津天成制药有限公司 | 乙酰左旋肉碱硝酸盐的制备方法 |
| CN106045919B (zh) * | 2016-07-07 | 2022-08-09 | 湖北楚维药业有限公司 | 一种左旋肉碱乳清酸盐的制备方法 |
| CN106748845B (zh) * | 2016-12-23 | 2018-11-20 | 东北制药集团股份有限公司 | 一种左旋肉碱盐微粉的制备方法 |
| CN112250588B (zh) * | 2020-11-06 | 2023-03-31 | 哈尔滨工业大学（深圳） | 一种左旋肉碱离子液体及其制备方法、应用 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR5656M (el) * | 1965-10-12 | 1967-12-26 | ||
| EP0150688B1 (en) * | 1983-12-28 | 1987-04-22 | Sigma-Tau Industrie Farmaceutiche Riunite S.p.A. | Salts of l-carnitine and alkanoyl l-carnitines and process for preparing same |
| US5073376A (en) * | 1989-12-22 | 1991-12-17 | Lonza Ltd. | Preparations containing l-carnitine |
| IT1258370B (it) * | 1992-03-02 | 1996-02-26 | Sigma Tau Ind Farmaceuti | Esteri della l-carnitina e di acil l-carnitine dotati di attivita' miorilassante selettiva sull'apparato gastro-intestinale e composizioni farmaceutiche che li contengono. |
| IT1261808B (it) * | 1993-07-06 | 1996-06-03 | Impiego di l-carnitina o acido l-carnitine e valproato nel trattamentodei disosrdini convulsivi |
-
1997
- 1997-05-26 PL PL97330189A patent/PL188558B1/pl unknown
- 1997-05-26 AU AU29612/97A patent/AU718308B2/en not_active Expired
- 1997-05-26 EE EE9800422A patent/EE03604B1/xx unknown
- 1997-05-26 BR BR9709627A patent/BR9709627A/pt not_active IP Right Cessation
- 1997-05-26 CZ CZ19983915A patent/CZ290902B6/cs not_active IP Right Cessation
- 1997-05-26 IL IL12726697A patent/IL127266A/en not_active IP Right Cessation
- 1997-05-26 WO PCT/EP1997/002693 patent/WO1997046512A1/en active IP Right Grant
- 1997-05-26 DE DE69704561T patent/DE69704561T2/de not_active Expired - Lifetime
- 1997-05-26 AT AT97924007T patent/ATE200479T1/de active
- 1997-05-26 SK SK1649-98A patent/SK283105B6/sk not_active IP Right Cessation
- 1997-05-26 HU HU9903455A patent/HU228008B1/hu unknown
- 1997-05-26 DK DK97924007T patent/DK0914315T3/da active
- 1997-05-26 NZ NZ333061A patent/NZ333061A/xx not_active IP Right Cessation
- 1997-05-26 TR TR1998/02492T patent/TR199802492T2/xx unknown
- 1997-05-26 PT PT97924007T patent/PT914315E/pt unknown
- 1997-05-26 US US09/194,608 patent/US5952379A/en not_active Expired - Lifetime
- 1997-05-26 JP JP50017398A patent/JP4160634B2/ja not_active Expired - Lifetime
- 1997-05-26 ES ES97924007T patent/ES2156381T3/es not_active Expired - Lifetime
- 1997-05-26 CN CNB971951454A patent/CN1177807C/zh not_active Expired - Lifetime
- 1997-05-26 EP EP97924007A patent/EP0914315B1/en not_active Expired - Lifetime
-
1998
- 1998-11-27 NO NO19985562A patent/NO323593B1/no not_active IP Right Cessation
- 1998-11-30 IS IS4914A patent/IS2085B/is unknown
-
2000
- 2000-06-21 HK HK00103735A patent/HK1024463A1/xx not_active IP Right Cessation
-
2001
- 2001-05-31 GR GR20010400820T patent/GR3035969T3/el unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5952379A (en) | Stable, non-hygroscopic salts of L(-)carnitine and alkanoyl L(-)carnitines, a process for their preparation and solid, orally administrable compositions containing such salts | |
| CA2281630C (en) | Process for the preparation of stable, non-hygroscopic salts of l(-)carnitine | |
| US7728037B2 (en) | Alpha-ketoglutarates of active ingredients and compositions containing same | |
| AU2002215203A1 (en) | Alpha-ketoglutarates of active ingredients and compositions containing same | |
| CA2256712C (en) | Stable, non-hygroscopic salts of l(-)carnitine and alkanoyl l(-)carnitines, a process for their preparation and solid, orally administrable compositions containing such salts | |
| AU733272B2 (en) | Solid compositions suitable for oral administration comprising non hygroscopic salts of L-carnitine and alkanoyl-L-carnitine with 2-aminoethanesulfonic acid | |
| KR100506163B1 (ko) | L(-)카르니틴및알카노일l(-)카르니틴의안정한비-흡습성염화합물,그제조방법및상기염화합물을포함하는고형의경구투여용조성물 | |
| MXPA98010098A (en) | Stable non-hygroscopic salts of l (-) carnitine and alcanoil-l (-) carnitines, a procedure for their preparation, and solid oral organically administrative compositions containing dichas sa | |
| MXPA99007888A (en) | Process for the preparation of stable, non-hygroscopic salts of l(-)carnitine and alkanoyl l(-)carnitines |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FF | Patent granted | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| EXP | Patent expired |