CH651015A5 - Carnitinammidi di amminoacidi otticamente attivi e procedimenti per la loro preparazione. - Google Patents
Carnitinammidi di amminoacidi otticamente attivi e procedimenti per la loro preparazione. Download PDFInfo
- Publication number
- CH651015A5 CH651015A5 CH560/81A CH56081A CH651015A5 CH 651015 A5 CH651015 A5 CH 651015A5 CH 560/81 A CH560/81 A CH 560/81A CH 56081 A CH56081 A CH 56081A CH 651015 A5 CH651015 A5 CH 651015A5
- Authority
- CH
- Switzerland
- Prior art keywords
- carnitine
- amide
- mixture
- formula
- amino acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 35
- 238000002360 preparation method Methods 0.000 title claims description 17
- 150000001413 amino acids Chemical class 0.000 title claims description 11
- 150000001408 amides Chemical class 0.000 claims description 40
- -1 aliphatic radical Chemical class 0.000 claims description 35
- 239000000203 mixture Substances 0.000 claims description 32
- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical compound C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 claims description 30
- 239000000243 solution Substances 0.000 claims description 29
- 229960004203 carnitine Drugs 0.000 claims description 27
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 26
- MEFKEPWMEQBLKI-AIRLBKTGSA-O S-adenosyl-L-methionine Chemical compound O[C@@H]1[C@H](O)[C@@H](C[S+](CC[C@H]([NH3+])C([O-])=O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 MEFKEPWMEQBLKI-AIRLBKTGSA-O 0.000 claims description 17
- 229940024606 amino acid Drugs 0.000 claims description 15
- 235000001014 amino acid Nutrition 0.000 claims description 15
- 238000003756 stirring Methods 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 10
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- 230000015572 biosynthetic process Effects 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 238000002425 crystallisation Methods 0.000 claims description 7
- 230000008025 crystallization Effects 0.000 claims description 7
- 229960002989 glutamic acid Drugs 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- 239000002244 precipitate Substances 0.000 claims description 7
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 claims description 6
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 6
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 6
- 239000000706 filtrate Substances 0.000 claims description 6
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 5
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- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
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- ZGUNAGUHMKGQNY-ZETCQYMHSA-N L-alpha-phenylglycine zwitterion Chemical compound OC(=O)[C@@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-ZETCQYMHSA-N 0.000 claims description 4
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 claims description 4
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- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims description 4
- KWIXGIMKELMNGH-UHFFFAOYSA-O carnitinamide Chemical compound C[N+](C)(C)CC(O)CC(N)=O KWIXGIMKELMNGH-UHFFFAOYSA-O 0.000 claims description 4
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
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- QDGAVODICPCDMU-UHFFFAOYSA-N 2-amino-3-[3-[bis(2-chloroethyl)amino]phenyl]propanoic acid Chemical compound OC(=O)C(N)CC1=CC=CC(N(CCCl)CCCl)=C1 QDGAVODICPCDMU-UHFFFAOYSA-N 0.000 claims description 2
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- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 claims 1
- 125000000539 amino acid group Chemical group 0.000 claims 1
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
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- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 claims 1
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 238000005481 NMR spectroscopy Methods 0.000 description 14
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- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 12
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 11
- 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 11
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- PHIQHXFUZVPYII-UHFFFAOYSA-N carnitine Chemical compound C[N+](C)(C)CC(O)CC([O-])=O PHIQHXFUZVPYII-UHFFFAOYSA-N 0.000 description 4
- UIHPNZDZCOEZEN-YFKPBYRVSA-N methyl (2s)-2-amino-4-methylsulfanylbutanoate Chemical compound COC(=O)[C@@H](N)CCSC UIHPNZDZCOEZEN-YFKPBYRVSA-N 0.000 description 4
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- GJTJQSPLLQWKMB-BKZSKYJJSA-N (3R)-5-deuterio-3-hydroxy-4-oxo-3-[(trimethylazaniumyl)methyl]pentanoate Chemical compound C(C[2H])(=O)[C@](O)(C[N+](C)(C)C)CC([O-])=O GJTJQSPLLQWKMB-BKZSKYJJSA-N 0.000 description 2
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- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 238000012795 verification Methods 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
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
- C07C237/12—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/57—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
- C07C323/58—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton
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 |
|---|---|---|---|
| IT47749/80A IT1144077B (it) | 1980-01-29 | 1980-01-29 | Carnitinammidi di amminoacidi otticamente attivi e procedimento per la loro preparazione |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH651015A5 true CH651015A5 (it) | 1985-08-30 |
Family
ID=11262265
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH560/81A CH651015A5 (it) | 1980-01-29 | 1981-01-28 | Carnitinammidi di amminoacidi otticamente attivi e procedimenti per la loro preparazione. |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4343947A (cg-RX-API-DMAC7.html) |
| JP (1) | JPS56110654A (cg-RX-API-DMAC7.html) |
| BE (1) | BE887112A (cg-RX-API-DMAC7.html) |
| CA (1) | CA1167453A (cg-RX-API-DMAC7.html) |
| CH (1) | CH651015A5 (cg-RX-API-DMAC7.html) |
| DE (1) | DE3100133A1 (cg-RX-API-DMAC7.html) |
| ES (1) | ES498881A0 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2474489A1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB2068946B (cg-RX-API-DMAC7.html) |
| IT (1) | IT1144077B (cg-RX-API-DMAC7.html) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1248323B (it) * | 1991-05-16 | 1995-01-05 | Sigma Tau Ind Farmaceuti | Ammidi con amminoacidi naturali di alcanoil l-carnitine quali inibitori della degenerazione neuronale e attivatori dei processi di apprendimento e memorizzazione e per il trattamento del coma e composizioni farmaceutiche comprendenti tali composti |
| IT1261231B (it) * | 1993-04-08 | 1996-05-09 | Sigma Tau Ind Farmaceuti | Procedimento migliorato per la preparazione di l-(-)-carnitina a partire da un prodotto di scarto avente opposta configurazione. |
| US5958886A (en) * | 1998-01-13 | 1999-09-28 | Sigma-Tau Pharmaceuticals, Inc. | Carnitine-containing peptides and a method for using the same |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3265719A (en) * | 1959-12-28 | 1966-08-09 | American Cyanamid Co | Betaines |
| US3979441A (en) * | 1969-06-11 | 1976-09-07 | The Lubrizol Corporation | Oil-soluble polymers of N-3-aminoalkyl acrylamides, and lubricants containing them |
| US4116962A (en) * | 1976-12-03 | 1978-09-26 | E. R. Squibb & Sons, Inc. | Pyrrolidine and piperidine-2-carboxylic acid derivatives |
| 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 |
| US4252802A (en) * | 1980-03-13 | 1981-02-24 | E. R. Squibb & Sons, Inc. | Hydroxamic acid derivatives of 7-[(2-amino-4-thiazolyl)-oximino] cephalosporins |
-
1980
- 1980-01-29 IT IT47749/80A patent/IT1144077B/it active
- 1980-12-29 US US06/220,492 patent/US4343947A/en not_active Expired - Lifetime
-
1981
- 1981-01-05 DE DE3100133A patent/DE3100133A1/de not_active Withdrawn
- 1981-01-16 BE BE0/203511A patent/BE887112A/fr not_active IP Right Cessation
- 1981-01-21 CA CA000368952A patent/CA1167453A/en not_active Expired
- 1981-01-23 JP JP954981A patent/JPS56110654A/ja active Granted
- 1981-01-28 FR FR8101593A patent/FR2474489A1/fr active Granted
- 1981-01-28 CH CH560/81A patent/CH651015A5/it not_active IP Right Cessation
- 1981-01-28 ES ES498881A patent/ES498881A0/es active Granted
- 1981-01-29 GB GB8102766A patent/GB2068946B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES8207128A1 (es) | 1982-09-01 |
| US4343947A (en) | 1982-08-10 |
| JPH034539B2 (cg-RX-API-DMAC7.html) | 1991-01-23 |
| CA1167453A (en) | 1984-05-15 |
| DE3100133A1 (de) | 1981-11-19 |
| IT1144077B (it) | 1986-10-29 |
| FR2474489B1 (cg-RX-API-DMAC7.html) | 1984-05-18 |
| JPS56110654A (en) | 1981-09-01 |
| ES498881A0 (es) | 1982-09-01 |
| GB2068946B (en) | 1983-07-13 |
| BE887112A (fr) | 1981-05-14 |
| FR2474489A1 (fr) | 1981-07-31 |
| GB2068946A (en) | 1981-08-19 |
| IT8047749A0 (it) | 1980-01-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |