GB766246A - Phenyl-ethyl-acetyl methionine and the process of preparing same - Google Patents
Phenyl-ethyl-acetyl methionine and the process of preparing sameInfo
- Publication number
- GB766246A GB766246A GB8797/55A GB879755A GB766246A GB 766246 A GB766246 A GB 766246A GB 8797/55 A GB8797/55 A GB 8797/55A GB 879755 A GB879755 A GB 879755A GB 766246 A GB766246 A GB 766246A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenyl
- ethyl
- methionine
- acetyl
- reaction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- GZMXRXJDXGRWSZ-OAHLLOKOSA-N C1(=CC=CC=C1)[C@](N(C(C)=O)CC)(CCSC)C(=O)O Chemical compound C1(=CC=CC=C1)[C@](N(C(C)=O)CC)(CCSC)C(=O)O GZMXRXJDXGRWSZ-OAHLLOKOSA-N 0.000 title abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 abstract 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 abstract 2
- 229930182817 methionine Natural products 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- WYSSLNYRXLESCD-ZDUSSCGKSA-N (2S)-2-(N-butanoylanilino)-4-methylsulfanylbutanoic acid Chemical compound C1(=CC=CC=C1)N([C@@H](CCSC)C(=O)O)C(CCC)=O WYSSLNYRXLESCD-ZDUSSCGKSA-N 0.000 abstract 1
- QGXMHCMPIAYMGT-UHFFFAOYSA-N 2-phenylbutanoyl chloride Chemical compound CCC(C(Cl)=O)C1=CC=CC=C1 QGXMHCMPIAYMGT-UHFFFAOYSA-N 0.000 abstract 1
- 208000035150 Hypercholesterolemia Diseases 0.000 abstract 1
- 229920002472 Starch Polymers 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 235000019359 magnesium stearate Nutrition 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- -1 phenyl-ethyl-acetyl halide Chemical class 0.000 abstract 1
- 239000008107 starch Substances 0.000 abstract 1
- 235000019698 starch Nutrition 0.000 abstract 1
- 239000000454 talc Substances 0.000 abstract 1
- 229910052623 talc Inorganic materials 0.000 abstract 1
- 235000012222 talc Nutrition 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/26—Separation; Purification; Stabilisation; Use of additives
- C07C319/28—Separation; Purification
-
- 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
- C07C323/60—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 with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The invention comprises phenyl-ethyl-acetyl methionine of the formula <FORM:0766246/IV(b)/1> and its preparation of reaction of methionine with a phenyl-ethyl-acetyl halide under alkaline conditions. Suitably the reaction is carried out in the presence of a strong base such as sodium hydroxide, to maintain a pH of at least 9, at a temperature which does not exceed 15-20 DEG C. In an example, phenyl-ethyl-acetyl chloride is reacted with methionine in aqueous sodium hydroxide and the resulting phenyl-ethylacetyl methionine is recrystallized from benzene or acetone.ALSO:Therapeutic compositions for the treatment of hypercholesterolemia comprise phenyl - ethyl - acetyl methionine of the formula:- <FORM:0766246/VI/1> (see Group IV(b)) in tablets containing 0.40 gm. of the compound with an excipient consisting for example of a mixture of starch, magnesium stearate and talc.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR766246X | 1954-03-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB766246A true GB766246A (en) | 1957-01-16 |
Family
ID=9183198
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8797/55A Expired GB766246A (en) | 1954-03-25 | 1955-03-25 | Phenyl-ethyl-acetyl methionine and the process of preparing same |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB766246A (en) |
-
1955
- 1955-03-25 GB GB8797/55A patent/GB766246A/en not_active Expired
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