LU84244A1 - Procede de preparation de chlorure de carnitine - Google Patents
Procede de preparation de chlorure de carnitine Download PDFInfo
- Publication number
- LU84244A1 LU84244A1 LU84244A LU84244A LU84244A1 LU 84244 A1 LU84244 A1 LU 84244A1 LU 84244 A LU84244 A LU 84244A LU 84244 A LU84244 A LU 84244A LU 84244 A1 LU84244 A1 LU 84244A1
- Authority
- LU
- Luxembourg
- Prior art keywords
- carnitine
- chloride
- hours
- preparation
- acid chloride
- Prior art date
Links
- PHIQHXFUZVPYII-UHFFFAOYSA-N carnitine Chemical compound C[N+](C)(C)CC(O)CC([O-])=O PHIQHXFUZVPYII-UHFFFAOYSA-N 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 7
- 229960000678 carnitine chloride Drugs 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 4
- 229960004203 carnitine Drugs 0.000 claims description 21
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 14
- 239000012320 chlorinating reagent Substances 0.000 claims description 8
- 230000035484 reaction time Effects 0.000 claims description 7
- 238000005660 chlorination reaction Methods 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- PHIQHXFUZVPYII-ZCFIWIBFSA-O (R)-carnitinium Chemical compound C[N+](C)(C)C[C@H](O)CC(O)=O PHIQHXFUZVPYII-ZCFIWIBFSA-O 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- HRQGCQVOJVTVLU-UHFFFAOYSA-N bis(chloromethyl) ether Chemical compound ClCOCCl HRQGCQVOJVTVLU-UHFFFAOYSA-N 0.000 claims 1
- 125000003431 oxalo group Chemical group 0.000 claims 1
- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical class C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 description 20
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 12
- GUYHPGUANSLONG-SNAWJCMRSA-N (E)-4-(trimethylammonio)but-2-enoate Chemical compound C[N+](C)(C)C\C=C\C([O-])=O GUYHPGUANSLONG-SNAWJCMRSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000004702 methyl esters Chemical class 0.000 description 5
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- HKYGSMOFSFOEIP-UHFFFAOYSA-N dichloro(dichloromethoxy)methane Chemical compound ClC(Cl)OC(Cl)Cl HKYGSMOFSFOEIP-UHFFFAOYSA-N 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- -1 for example Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 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 description 1
- 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 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001277 beta hydroxy acids Chemical class 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/363—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- 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
- C07C59/01—Saturated compounds having only one carboxyl group and containing hydroxy or O-metal groups
- C07C59/115—Saturated compounds having only one carboxyl group and containing hydroxy or O-metal groups containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (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 |
|---|---|---|---|
| IT48817/81A IT1171360B (it) | 1981-07-03 | 1981-07-03 | Procedimento per la preparazione del cloruro acido di carnitina |
| IT4881781 | 1981-07-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| LU84244A1 true LU84244A1 (fr) | 1983-01-20 |
Family
ID=11268676
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU84244A LU84244A1 (fr) | 1981-07-03 | 1982-06-30 | Procede de preparation de chlorure de carnitine |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS5815943A (de) |
| KR (1) | KR860001886B1 (de) |
| AT (1) | AT390057B (de) |
| BE (1) | BE893713A (de) |
| CA (1) | CA1186332A (de) |
| CH (1) | CH648546A5 (de) |
| DE (1) | DE3224666A1 (de) |
| DK (1) | DK154425C (de) |
| ES (1) | ES513658A0 (de) |
| FR (1) | FR2510559B1 (de) |
| GB (1) | GB2101133B (de) |
| GR (1) | GR76546B (de) |
| IE (1) | IE53279B1 (de) |
| IL (1) | IL66251A0 (de) |
| IT (1) | IT1171360B (de) |
| LU (1) | LU84244A1 (de) |
| NL (1) | NL189666C (de) |
| SE (1) | SE448724B (de) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1190358B (it) * | 1985-05-24 | 1988-02-16 | Sclavo Spa | Procedimento per la preparazione di l-carnitina |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3940439A (en) * | 1973-11-14 | 1976-02-24 | G. D. Searle & Co. | Acid chloride synthesis |
| IT1116037B (it) * | 1979-04-23 | 1986-02-10 | Sigma Tau Ind Farmaceuti | Esteri e ammidi di acil carnitine loro procedimenti di preparazione e loro uso terapeutico |
| DE2943433A1 (de) * | 1979-10-26 | 1981-05-07 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von carbonsaeurehalogeniden |
-
1981
- 1981-07-03 IT IT48817/81A patent/IT1171360B/it active
-
1982
- 1982-06-24 CH CH3884/82A patent/CH648546A5/it not_active IP Right Cessation
- 1982-06-25 IE IE1524/82A patent/IE53279B1/en not_active IP Right Cessation
- 1982-06-29 GB GB08218824A patent/GB2101133B/en not_active Expired
- 1982-06-30 DK DK295482A patent/DK154425C/da not_active IP Right Cessation
- 1982-06-30 BE BE0/208502A patent/BE893713A/fr not_active IP Right Cessation
- 1982-06-30 LU LU84244A patent/LU84244A1/fr unknown
- 1982-06-30 CA CA000406463A patent/CA1186332A/en not_active Expired
- 1982-07-01 KR KR8202945A patent/KR860001886B1/ko active
- 1982-07-01 GR GR68615A patent/GR76546B/el unknown
- 1982-07-01 DE DE19823224666 patent/DE3224666A1/de active Granted
- 1982-07-02 AT AT0257382A patent/AT390057B/de not_active IP Right Cessation
- 1982-07-02 SE SE8204117A patent/SE448724B/sv not_active IP Right Cessation
- 1982-07-02 JP JP57116084A patent/JPS5815943A/ja active Granted
- 1982-07-02 ES ES513658A patent/ES513658A0/es active Granted
- 1982-07-02 FR FR8211685A patent/FR2510559B1/fr not_active Expired
- 1982-07-02 NL NLAANVRAGE8202677,A patent/NL189666C/xx not_active IP Right Cessation
- 1982-07-07 IL IL66251A patent/IL66251A0/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| SE8204117D0 (sv) | 1982-07-02 |
| GB2101133B (en) | 1985-08-14 |
| ES8304064A1 (es) | 1983-03-01 |
| NL189666C (nl) | 1993-06-16 |
| NL8202677A (nl) | 1983-02-01 |
| ATA257382A (de) | 1989-08-15 |
| JPH0244300B2 (de) | 1990-10-03 |
| IL66251A0 (en) | 1982-11-30 |
| BE893713A (fr) | 1982-10-18 |
| ES513658A0 (es) | 1983-03-01 |
| FR2510559B1 (fr) | 1986-05-09 |
| AT390057B (de) | 1990-03-12 |
| IT1171360B (it) | 1987-06-10 |
| KR860001886B1 (ko) | 1986-10-24 |
| DK154425B (da) | 1988-11-14 |
| GR76546B (de) | 1984-08-10 |
| IT8148817A0 (it) | 1981-07-03 |
| CA1186332A (en) | 1985-04-30 |
| CH648546A5 (it) | 1985-03-29 |
| DK154425C (da) | 1989-04-10 |
| DE3224666A1 (de) | 1983-01-20 |
| JPS5815943A (ja) | 1983-01-29 |
| SE8204117L (sv) | 1983-01-04 |
| IE821524L (en) | 1983-01-03 |
| DK295482A (da) | 1983-01-04 |
| SE448724B (sv) | 1987-03-16 |
| IE53279B1 (en) | 1988-09-28 |
| GB2101133A (en) | 1983-01-12 |
| KR840000475A (ko) | 1984-02-22 |
| DE3224666C2 (de) | 1991-01-24 |
| FR2510559A1 (fr) | 1983-02-04 |
| NL189666B (nl) | 1993-01-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| DT | Application date | ||
| TA | Annual fee |