IL140487A - Non-hygroscopic salts of L - carnitine and alkanoyl L - carnitines with pamoic acid and pharmaceuticals containing them - Google Patents
Non-hygroscopic salts of L - carnitine and alkanoyl L - carnitines with pamoic acid and pharmaceuticals containing themInfo
- Publication number
- IL140487A IL140487A IL14048799A IL14048799A IL140487A IL 140487 A IL140487 A IL 140487A IL 14048799 A IL14048799 A IL 14048799A IL 14048799 A IL14048799 A IL 14048799A IL 140487 A IL140487 A IL 140487A
- Authority
- IL
- Israel
- Prior art keywords
- alkanoyl
- carnitine
- salt
- pamoic acid
- salts
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 43
- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical class C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 title claims abstract description 32
- -1 alkanoyl l-carnitines Chemical class 0.000 title claims abstract description 21
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 229960001518 levocarnitine Drugs 0.000 title claims 2
- 239000008194 pharmaceutical composition Substances 0.000 title description 2
- 125000001589 carboacyl group Chemical group 0.000 claims abstract description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 22
- 235000015872 dietary supplement Nutrition 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 239000004615 ingredient Substances 0.000 claims description 5
- 239000000047 product Substances 0.000 claims description 5
- 238000013270 controlled release Methods 0.000 claims description 4
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 3
- 239000002775 capsule Substances 0.000 claims description 3
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 239000003826 tablet 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
- 239000007910 chewable tablet Substances 0.000 claims description 2
- 235000005911 diet Nutrition 0.000 claims description 2
- 230000000378 dietary effect Effects 0.000 claims description 2
- 239000008187 granular material Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 239000000843 powder 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
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 229940127557 pharmaceutical product Drugs 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 description 16
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 9
- UFAHZIUFPNSHSL-MRVPVSSYSA-N O-propanoyl-L-carnitine Chemical compound CCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C UFAHZIUFPNSHSL-MRVPVSSYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 230000001225 therapeutic effect Effects 0.000 description 6
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 6
- 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
- 230000036765 blood level Effects 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 235000013305 food Nutrition 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 239000002417 nutraceutical Substances 0.000 description 4
- 235000021436 nutraceutical agent Nutrition 0.000 description 4
- 235000016709 nutrition Nutrition 0.000 description 4
- 229960004203 carnitine Drugs 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 2
- 239000008116 calcium stearate Substances 0.000 description 2
- 235000013539 calcium stearate Nutrition 0.000 description 2
- 230000001684 chronic effect Effects 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 230000036449 good health Effects 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 208000031225 myocardial ischemia Diseases 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 239000008247 solid mixture Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 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
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 208000007101 Muscle Cramp Diseases 0.000 description 1
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 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
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 230000006793 arrhythmia Effects 0.000 description 1
- 206010003549 asthenia Diseases 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 235000013402 health food Nutrition 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000037356 lipid metabolism Effects 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 230000003387 muscular Effects 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 230000009993 protective function Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 210000002027 skeletal muscle Anatomy 0.000 description 1
- 235000021476 total parenteral nutrition Nutrition 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
-
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
- C07C65/105—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups polycyclic
- C07C65/11—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups polycyclic with carboxyl groups on a condensed ring system containing two rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nutrition Science (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT98RM000445A IT1299544B1 (it) | 1998-07-03 | 1998-07-03 | Composizioni solide atte alla somministrazione orale comprendenti sali non igroscopici della l-carnitina e delle alcanoil l-carnitine |
| PCT/IT1999/000202 WO2000001662A1 (en) | 1998-07-03 | 1999-07-02 | Solid compositions suitable for oral administration containing non-hygroscopic salts of l-carnitine and alkanoyl l-carnitines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL140487A0 IL140487A0 (en) | 2002-02-10 |
| IL140487A true IL140487A (en) | 2004-07-25 |
Family
ID=11406029
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL14048799A IL140487A (en) | 1998-07-03 | 1999-07-02 | Non-hygroscopic salts of L - carnitine and alkanoyl L - carnitines with pamoic acid and pharmaceuticals containing them |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US6465515B2 (pt) |
| EP (1) | EP1093451B1 (pt) |
| JP (1) | JP2002519403A (pt) |
| KR (1) | KR100642729B1 (pt) |
| AT (1) | ATE248805T1 (pt) |
| AU (1) | AU4647999A (pt) |
| CA (1) | CA2335503A1 (pt) |
| DE (1) | DE69911021T2 (pt) |
| DK (1) | DK1093451T3 (pt) |
| ES (1) | ES2205843T3 (pt) |
| HK (1) | HK1035710A1 (pt) |
| IL (1) | IL140487A (pt) |
| IT (1) | IT1299544B1 (pt) |
| PT (1) | PT1093451E (pt) |
| WO (1) | WO2000001662A1 (pt) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1317048B1 (it) * | 2000-06-23 | 2003-05-26 | Sigma Tau Ind Farmaceuti | Uso dell'acido pamoico o di un suo derivato, o di un suo analogo, perla preparazione di un medicamento per il trattamento di patologie |
| JP2006111550A (ja) * | 2004-10-13 | 2006-04-27 | Nisshin Pharma Inc | カルニチン含有製品 |
| EP4362697A1 (en) * | 2021-06-07 | 2024-05-08 | Kaesler Nutrition GmbH | Carnitine formulation |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2008578A (en) * | 1977-11-03 | 1979-06-06 | Sigma Tau Ind Farmaceuti | I-Carnitine derivatives |
| 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 |
| IT1209564B (it) * | 1984-06-29 | 1989-08-30 | Magis Farmaceutici | Derivati della l-carnitina o di l-acil carnitina. |
| IT1188176B (it) * | 1985-07-05 | 1988-01-07 | Bicresearch Spa | Sali della carnitina particolarmente idonei per uso orale |
| DE3841664A1 (de) * | 1988-12-10 | 1990-10-11 | Fresenius Ag | Nicht-hygroskopisches salz des l-carnitins |
| US5073376A (en) * | 1989-12-22 | 1991-12-17 | Lonza Ltd. | Preparations containing l-carnitine |
-
1998
- 1998-07-03 IT IT98RM000445A patent/IT1299544B1/it active IP Right Grant
-
1999
- 1999-07-02 KR KR1020017000060A patent/KR100642729B1/ko not_active IP Right Cessation
- 1999-07-02 AT AT99929707T patent/ATE248805T1/de not_active IP Right Cessation
- 1999-07-02 WO PCT/IT1999/000202 patent/WO2000001662A1/en active IP Right Grant
- 1999-07-02 DK DK99929707T patent/DK1093451T3/da active
- 1999-07-02 CA CA002335503A patent/CA2335503A1/en not_active Abandoned
- 1999-07-02 JP JP2000558067A patent/JP2002519403A/ja active Pending
- 1999-07-02 IL IL14048799A patent/IL140487A/en not_active IP Right Cessation
- 1999-07-02 AU AU46479/99A patent/AU4647999A/en not_active Abandoned
- 1999-07-02 PT PT99929707T patent/PT1093451E/pt unknown
- 1999-07-02 ES ES99929707T patent/ES2205843T3/es not_active Expired - Lifetime
- 1999-07-02 EP EP99929707A patent/EP1093451B1/en not_active Expired - Lifetime
- 1999-07-02 DE DE69911021T patent/DE69911021T2/de not_active Expired - Fee Related
-
2000
- 2000-12-21 US US09/740,786 patent/US6465515B2/en not_active Expired - Fee Related
-
2001
- 2001-07-10 HK HK01104772A patent/HK1035710A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CA2335503A1 (en) | 2000-01-13 |
| DE69911021D1 (de) | 2003-10-09 |
| ITRM980445A1 (it) | 2000-01-03 |
| KR100642729B1 (ko) | 2006-11-03 |
| DE69911021T2 (de) | 2004-04-01 |
| AU4647999A (en) | 2000-01-24 |
| US6465515B2 (en) | 2002-10-15 |
| EP1093451A1 (en) | 2001-04-25 |
| ITRM980445A0 (it) | 1998-07-03 |
| ES2205843T3 (es) | 2004-05-01 |
| IL140487A0 (en) | 2002-02-10 |
| HK1035710A1 (en) | 2001-12-07 |
| KR20010071720A (ko) | 2001-07-31 |
| WO2000001662A1 (en) | 2000-01-13 |
| US20010009923A1 (en) | 2001-07-26 |
| DK1093451T3 (da) | 2004-01-05 |
| PT1093451E (pt) | 2003-12-31 |
| JP2002519403A (ja) | 2002-07-02 |
| EP1093451B1 (en) | 2003-09-03 |
| IT1299544B1 (it) | 2000-03-16 |
| ATE248805T1 (de) | 2003-09-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FF | Patent granted | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| MM9K | Patent not in force due to non-payment of renewal fees |