CZ303031B6 - Postup prípravy solí L-karnitinu a alkanoyl-L-karnitinu s kyselinou slizovou - Google Patents
Postup prípravy solí L-karnitinu a alkanoyl-L-karnitinu s kyselinou slizovou Download PDFInfo
- Publication number
- CZ303031B6 CZ303031B6 CZ20022533A CZ20022533A CZ303031B6 CZ 303031 B6 CZ303031 B6 CZ 303031B6 CZ 20022533 A CZ20022533 A CZ 20022533A CZ 20022533 A CZ20022533 A CZ 20022533A CZ 303031 B6 CZ303031 B6 CZ 303031B6
- Authority
- CZ
- Czechia
- Prior art keywords
- carnitine
- alkanoyl
- solution
- chloride
- precipitate
- 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
- 150000003839 salts Chemical class 0.000 title claims abstract description 25
- 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 abstract description 12
- 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 abstract description 12
- -1 alkanoyl L-carnitine Chemical class 0.000 title abstract description 7
- 238000004519 manufacturing process Methods 0.000 title abstract description 4
- 239000000243 solution Substances 0.000 claims abstract description 16
- 238000001035 drying Methods 0.000 claims abstract description 8
- 239000002244 precipitate Substances 0.000 claims abstract description 8
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- 238000003756 stirring Methods 0.000 claims abstract description 4
- 239000003960 organic solvent Substances 0.000 claims abstract description 3
- 230000001376 precipitating effect Effects 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- 239000007864 aqueous solution Substances 0.000 claims description 8
- 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 4
- 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 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- 239000012153 distilled water Substances 0.000 claims description 3
- 150000002500 ions Chemical class 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229960000678 carnitine chloride Drugs 0.000 claims description 2
- 230000000694 effects Effects 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
- 239000002904 solvent Substances 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 3
- 238000010790 dilution Methods 0.000 abstract description 2
- 239000012895 dilution Substances 0.000 abstract description 2
- JXXCENBLGFBQJM-UHFFFAOYSA-N (3-carboxy-2-hydroxypropyl)-trimethylazanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC(O)CC(O)=O JXXCENBLGFBQJM-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- 238000010923 batch production Methods 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 229920005989 resin Polymers 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 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000007787 solid Substances 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 150000001450 anions Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000007711 solidification Methods 0.000 description 2
- 230000008023 solidification Effects 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 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
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000320 mechanical mixture Substances 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 239000007790 solid phase Substances 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
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 (1)
| 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. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CZ20022533A3 CZ20022533A3 (cs) | 2003-02-12 |
| CZ303031B6 true CZ303031B6 (cs) | 2012-03-07 |
Family
ID=11454414
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ20022533A CZ303031B6 (cs) | 2000-02-10 | 2001-02-09 | Postup prípravy solí L-karnitinu a alkanoyl-L-karnitinu s kyselinou slizovou |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US6693215B2 (enExample) |
| EP (1) | EP1257524B1 (enExample) |
| JP (1) | JP4708655B2 (enExample) |
| KR (1) | KR100709629B1 (enExample) |
| CN (1) | CN1169781C (enExample) |
| AT (1) | ATE308509T1 (enExample) |
| AU (1) | AU2001234079A1 (enExample) |
| CA (1) | CA2399501C (enExample) |
| CZ (1) | CZ303031B6 (enExample) |
| DE (1) | DE60114572T2 (enExample) |
| DK (1) | DK1257524T3 (enExample) |
| ES (1) | ES2249411T3 (enExample) |
| HK (1) | HK1052682B (enExample) |
| HU (1) | HU226129B1 (enExample) |
| IT (1) | IT1316988B1 (enExample) |
| MX (1) | MXPA02007682A (enExample) |
| PL (1) | PL201605B1 (enExample) |
| SK (1) | SK287250B6 (enExample) |
| WO (1) | WO2001058850A1 (enExample) |
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 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5952379A (en) * | 1996-05-31 | 1999-09-14 | Sigma-Tau Industrie Farmaceutiche | Stable, non-hygroscopic salts of L(-)carnitine and alkanoyl L(-)carnitines, a process for their preparation and solid, orally administrable compositions containing such salts |
Family Cites Families (2)
| 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 |
-
2000
- 2000-02-10 IT IT2000RM000060A patent/IT1316988B1/it active
-
2001
- 2001-02-09 DK DK01906116T patent/DK1257524T3/da active
- 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
- 2001-02-09 CZ CZ20022533A patent/CZ303031B6/cs not_active IP Right Cessation
- 2001-02-09 PL PL358098A patent/PL201605B1/pl unknown
- 2001-02-09 EP EP01906116A patent/EP1257524B1/en not_active Expired - Lifetime
- 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 DE DE60114572T patent/DE60114572T2/de not_active Expired - Lifetime
- 2001-02-09 WO PCT/IT2001/000056 patent/WO2001058850A1/en not_active Ceased
- 2001-02-09 JP JP2001558402A patent/JP4708655B2/ja not_active Expired - Fee Related
- 2001-02-09 MX MXPA02007682A patent/MXPA02007682A/es active IP Right Grant
- 2001-02-09 KR KR1020027010247A patent/KR100709629B1/ko not_active Expired - Fee Related
- 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 AT AT01906116T patent/ATE308509T1/de active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5952379A (en) * | 1996-05-31 | 1999-09-14 | Sigma-Tau Industrie Farmaceutiche | Stable, non-hygroscopic salts of L(-)carnitine and alkanoyl L(-)carnitines, a process for their preparation and solid, orally administrable compositions containing such salts |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1398251A (zh) | 2003-02-19 |
| EP1257524B1 (en) | 2005-11-02 |
| WO2001058850A1 (en) | 2001-08-16 |
| HU226129B1 (en) | 2008-04-28 |
| HUP0204378A3 (en) | 2005-05-30 |
| PL358098A1 (en) | 2004-08-09 |
| SK287250B6 (sk) | 2010-04-07 |
| IT1316988B1 (it) | 2003-05-26 |
| HUP0204378A2 (hu) | 2003-04-28 |
| PL201605B1 (pl) | 2009-04-30 |
| ES2249411T3 (es) | 2006-04-01 |
| KR100709629B1 (ko) | 2007-04-19 |
| AU2001234079A1 (en) | 2001-08-20 |
| HK1052682B (zh) | 2005-05-06 |
| CA2399501C (en) | 2010-06-29 |
| US20030130539A1 (en) | 2003-07-10 |
| ATE308509T1 (de) | 2005-11-15 |
| DE60114572T2 (de) | 2006-07-27 |
| ITRM20000060A1 (it) | 2001-08-10 |
| SK11552002A3 (sk) | 2002-12-03 |
| US6693215B2 (en) | 2004-02-17 |
| DK1257524T3 (da) | 2006-02-13 |
| HK1052682A1 (en) | 2003-09-26 |
| EP1257524A1 (en) | 2002-11-20 |
| JP2003522749A (ja) | 2003-07-29 |
| KR20020073543A (ko) | 2002-09-26 |
| ITRM20000060A0 (it) | 2000-02-10 |
| CA2399501A1 (en) | 2001-08-16 |
| JP4708655B2 (ja) | 2011-06-22 |
| DE60114572D1 (de) | 2005-12-08 |
| CN1169781C (zh) | 2004-10-06 |
| MXPA02007682A (es) | 2003-01-28 |
| CZ20022533A3 (cs) | 2003-02-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed due to non-payment of fee |
Effective date: 20170209 |