SK287250B6 - Spôsob prípravy solí L-karnitínu a alkanoyl L-karnitínu s kyselinou galaktarovou - Google Patents
Spôsob prípravy solí L-karnitínu a alkanoyl L-karnitínu s kyselinou galaktarovou Download PDFInfo
- Publication number
- SK287250B6 SK287250B6 SK1155-2002A SK11552002A SK287250B6 SK 287250 B6 SK287250 B6 SK 287250B6 SK 11552002 A SK11552002 A SK 11552002A SK 287250 B6 SK287250 B6 SK 287250B6
- Authority
- SK
- Slovakia
- Prior art keywords
- carnitine
- alkanoyl
- chloride
- solution
- salt
- Prior art date
Links
- 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 28
- -1 alkanoyl L-carnitine Chemical class 0.000 title claims abstract description 28
- 238000000034 method Methods 0.000 title claims abstract description 22
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 150000003839 salts Chemical class 0.000 title claims description 31
- 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 title claims description 14
- 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 title claims description 14
- 238000003756 stirring Methods 0.000 claims abstract description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 15
- 239000000243 solution Substances 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 239000007864 aqueous solution Substances 0.000 claims description 8
- 238000001035 drying Methods 0.000 claims description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- JXXCENBLGFBQJM-FYZOBXCZSA-N [(2r)-3-carboxy-2-hydroxypropyl]-trimethylazanium;chloride Chemical compound [Cl-].C[N+](C)(C)C[C@H](O)CC(O)=O JXXCENBLGFBQJM-FYZOBXCZSA-N 0.000 claims description 5
- 239000003957 anion exchange resin Substances 0.000 claims description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 3
- 239000012153 distilled water Substances 0.000 claims description 3
- 238000005342 ion exchange Methods 0.000 claims description 3
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229940035429 isobutyl alcohol Drugs 0.000 claims description 2
- 239000007791 liquid phase Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 230000001376 precipitating effect Effects 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- JATPLOXBFFRHDN-DDWIOCJRSA-N [(2r)-2-acetyloxy-3-carboxypropyl]-trimethylazanium;chloride Chemical compound [Cl-].CC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C JATPLOXBFFRHDN-DDWIOCJRSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 229960000678 carnitine chloride Drugs 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 238000010790 dilution Methods 0.000 abstract description 2
- 239000012895 dilution Substances 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- 238000010923 batch production Methods 0.000 abstract 1
- 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 9
- 239000007787 solid Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- GJTJQSPLLQWKMB-SECBINFHSA-N (3R)-3-hydroxy-4-oxo-3-[(trimethylazaniumyl)methyl]pentanoate Chemical class C(C)(=O)[C@](O)(C[N+](C)(C)C)CC([O-])=O GJTJQSPLLQWKMB-SECBINFHSA-N 0.000 description 2
- 102100027324 2-hydroxyacyl-CoA lyase 1 Human genes 0.000 description 2
- 101001009252 Homo sapiens 2-hydroxyacyl-CoA lyase 1 Proteins 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 125000001589 carboacyl group Chemical group 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- KOXPMCGIACXQEH-FYZOBXCZSA-N (3r)-3-hydroxy-4-(trimethylazaniumyl)butanoate;propanoyl chloride Chemical compound CCC(Cl)=O.C[N+](C)(C)C[C@H](O)CC([O-])=O KOXPMCGIACXQEH-FYZOBXCZSA-N 0.000 description 1
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 description 1
- 229910000497 Amalgam Inorganic materials 0.000 description 1
- QWYFHHGCZUCMBN-SECBINFHSA-N O-butanoyl-L-carnitine Chemical compound CCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C QWYFHHGCZUCMBN-SECBINFHSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- HQOLZZWNPROYNV-FYZOBXCZSA-N acetyl chloride;(3r)-3-hydroxy-4-(trimethylazaniumyl)butanoate Chemical compound CC(Cl)=O.C[N+](C)(C)C[C@H](O)CC([O-])=O HQOLZZWNPROYNV-FYZOBXCZSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- IGQBPDJNUXPEMT-SNVBAGLBSA-N isovaleryl-L-carnitine Chemical compound CC(C)CC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C IGQBPDJNUXPEMT-SNVBAGLBSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000320 mechanical mixture Substances 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
Classifications
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2000RM000060A IT1316988B1 (it) | 2000-02-10 | 2000-02-10 | Procedimento migliorato di preparazione industriale di mucati dellal-carnitina e di alcanoil l-carnitine. |
| PCT/IT2001/000056 WO2001058850A1 (en) | 2000-02-10 | 2001-02-09 | A process for the preparation of salts of l-carnitine and alkanoyl l-carnitine with mucic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK11552002A3 SK11552002A3 (sk) | 2002-12-03 |
| SK287250B6 true SK287250B6 (sk) | 2010-04-07 |
Family
ID=11454414
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1155-2002A SK287250B6 (sk) | 2000-02-10 | 2001-02-09 | Spôsob prípravy solí L-karnitínu a alkanoyl L-karnitínu s kyselinou galaktarovou |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US6693215B2 (cs) |
| EP (1) | EP1257524B1 (cs) |
| JP (1) | JP4708655B2 (cs) |
| KR (1) | KR100709629B1 (cs) |
| CN (1) | CN1169781C (cs) |
| AT (1) | ATE308509T1 (cs) |
| AU (1) | AU2001234079A1 (cs) |
| CA (1) | CA2399501C (cs) |
| CZ (1) | CZ303031B6 (cs) |
| DE (1) | DE60114572T2 (cs) |
| DK (1) | DK1257524T3 (cs) |
| ES (1) | ES2249411T3 (cs) |
| HK (1) | HK1052682B (cs) |
| HU (1) | HU226129B1 (cs) |
| IT (1) | IT1316988B1 (cs) |
| MX (1) | MXPA02007682A (cs) |
| PL (1) | PL201605B1 (cs) |
| SK (1) | SK287250B6 (cs) |
| WO (1) | WO2001058850A1 (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN118638020B (zh) * | 2024-08-08 | 2024-11-19 | 杭州海尔希畜牧科技有限公司 | L-天门冬氨酸l(-)肉碱(1:1)的制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1172394B (it) * | 1983-12-28 | 1987-06-18 | Sigma Tau Ind Farmaceuti | Sali della l-carnitina e di alcuni alcanoil derivati della l-carnitina e procedimento per la loro preparazione |
| 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 |
| CN1177807C (zh) * | 1996-05-31 | 2004-12-01 | 希格马托制药工业公司 | 稳定的、非吸湿性的l(-)肉碱和链烷酰基l(-)肉碱的盐和其制备方法以及含有此盐的固体口服组合物 |
-
2000
- 2000-02-10 IT IT2000RM000060A patent/IT1316988B1/it active
-
2001
- 2001-02-09 AU AU2001234079A patent/AU2001234079A1/en not_active Abandoned
- 2001-02-09 CA CA2399501A patent/CA2399501C/en not_active Expired - Fee Related
- 2001-02-09 CZ CZ20022533A patent/CZ303031B6/cs not_active IP Right Cessation
- 2001-02-09 HK HK03104608.3A patent/HK1052682B/zh not_active IP Right Cessation
- 2001-02-09 US US10/203,565 patent/US6693215B2/en not_active Expired - Lifetime
- 2001-02-09 MX MXPA02007682A patent/MXPA02007682A/es active IP Right Grant
- 2001-02-09 WO PCT/IT2001/000056 patent/WO2001058850A1/en active IP Right Grant
- 2001-02-09 EP EP01906116A patent/EP1257524B1/en not_active Expired - Lifetime
- 2001-02-09 AT AT01906116T patent/ATE308509T1/de active
- 2001-02-09 JP JP2001558402A patent/JP4708655B2/ja not_active Expired - Fee Related
- 2001-02-09 PL PL358098A patent/PL201605B1/pl unknown
- 2001-02-09 DK DK01906116T patent/DK1257524T3/da active
- 2001-02-09 KR KR1020027010247A patent/KR100709629B1/ko not_active Expired - Fee Related
- 2001-02-09 DE DE60114572T patent/DE60114572T2/de not_active Expired - Lifetime
- 2001-02-09 CN CNB018047637A patent/CN1169781C/zh not_active Expired - Fee Related
- 2001-02-09 SK SK1155-2002A patent/SK287250B6/sk not_active IP Right Cessation
- 2001-02-09 ES ES01906116T patent/ES2249411T3/es not_active Expired - Lifetime
- 2001-02-09 HU HU0204378A patent/HU226129B1/hu not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| HK1052682B (zh) | 2005-05-06 |
| EP1257524B1 (en) | 2005-11-02 |
| CZ303031B6 (cs) | 2012-03-07 |
| MXPA02007682A (es) | 2003-01-28 |
| ITRM20000060A1 (it) | 2001-08-10 |
| WO2001058850A1 (en) | 2001-08-16 |
| US6693215B2 (en) | 2004-02-17 |
| DK1257524T3 (da) | 2006-02-13 |
| KR20020073543A (ko) | 2002-09-26 |
| SK11552002A3 (sk) | 2002-12-03 |
| AU2001234079A1 (en) | 2001-08-20 |
| DE60114572D1 (de) | 2005-12-08 |
| CZ20022533A3 (cs) | 2003-02-12 |
| ITRM20000060A0 (it) | 2000-02-10 |
| JP4708655B2 (ja) | 2011-06-22 |
| HK1052682A1 (en) | 2003-09-26 |
| KR100709629B1 (ko) | 2007-04-19 |
| PL201605B1 (pl) | 2009-04-30 |
| ATE308509T1 (de) | 2005-11-15 |
| CA2399501C (en) | 2010-06-29 |
| CA2399501A1 (en) | 2001-08-16 |
| JP2003522749A (ja) | 2003-07-29 |
| EP1257524A1 (en) | 2002-11-20 |
| HUP0204378A2 (hu) | 2003-04-28 |
| CN1169781C (zh) | 2004-10-06 |
| IT1316988B1 (it) | 2003-05-26 |
| ES2249411T3 (es) | 2006-04-01 |
| HU226129B1 (en) | 2008-04-28 |
| US20030130539A1 (en) | 2003-07-10 |
| CN1398251A (zh) | 2003-02-19 |
| PL358098A1 (en) | 2004-08-09 |
| HUP0204378A3 (en) | 2005-05-30 |
| DE60114572T2 (de) | 2006-07-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed due to non-payment of maintenance fees |
Effective date: 20170209 |