ES8604609A1 - Procedimiento para la obtencion de la 1-(n-(1(r,s)-(etoxi- carbonil)-3-fenilpropil)-l-alanil)-l-prolina - Google Patents
Procedimiento para la obtencion de la 1-(n-(1(r,s)-(etoxi- carbonil)-3-fenilpropil)-l-alanil)-l-prolinaInfo
- Publication number
- ES8604609A1 ES8604609A1 ES544781A ES544781A ES8604609A1 ES 8604609 A1 ES8604609 A1 ES 8604609A1 ES 544781 A ES544781 A ES 544781A ES 544781 A ES544781 A ES 544781A ES 8604609 A1 ES8604609 A1 ES 8604609A1
- Authority
- ES
- Spain
- Prior art keywords
- proline
- alanyl
- phenylpropyl
- ethoxycarbonyl
- preparation
- 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
- 229960002429 proline Drugs 0.000 title abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 abstract 2
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 239000002798 polar solvent Substances 0.000 abstract 2
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 abstract 1
- QNAYBMKLOCPYGJ-UWTATZPHSA-N L-Alanine Natural products C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 abstract 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 abstract 1
- 229930182821 L-proline Natural products 0.000 abstract 1
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 abstract 1
- 229960003767 alanine Drugs 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- 239000002274 desiccant Substances 0.000 abstract 1
- STPXIOGYOLJXMZ-UHFFFAOYSA-N ethyl 2-oxo-4-phenylbutanoate Chemical compound CCOC(=O)C(=O)CCC1=CC=CC=C1 STPXIOGYOLJXMZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002808 molecular sieve Substances 0.000 abstract 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- C07K5/022—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2
- C07K5/0222—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2 with the first amino acid being heterocyclic, e.g. Pro, Trp
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pyrrole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
PROCEDIMIENTO PARA LA OBTENCION DE LA 1-(N-(1(R,S)-(ETOXICARBONIL)-3-FENILPROPIL)-L-ALANIL)-L-PROLINA. CONSISTE EN PARTIR DEL 4-FENIL-2-OXOBUTIRATO DE ETILO Y HACERLO REACCIONAR CON LA L-ALANINA EN PRESENCIA DE UN AGENTE REDUCTOR COMO EL CIANOBOROHIDRURO DE SODIO O EL HIDROGENO EN PRESENCIA DE UN CATALIZADOR Y BAJO LA ACCION DE UN AGENTE DESECANTE, EN EL SENO DE UN DISOLVENTE POLAR, PARA OBTENER LA N-(1(R,S)-(ETOXICARBONIL)-3-FENILPROPIL)-L-ALANINA DE FORMULA (II) QUE POSTERIORMENTE SE HACE REACCIONAR CON LA N-HIDROXISUCCINIMIDA, EN PRESENCIA DE UN AGENTE CONDENSANTE Y EN UN DISOLVENTE POLAR PARA OBTENER LA N-(1(R,S)-(ETOXICARBONIL)-3-FENILPROPIL)-L-ALANINA DE FORMULA (III) QUE FINALMENTE SE HACE REACCIONAR CON LA L-PROLINA EN PRESENCIA DE UNA BASE Y EN UN DISOLVENTE POLAR PARA OBTENER EL PRODUCTO DESEADO DE FORMULA (I).
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES544781A ES8604609A1 (es) | 1985-07-02 | 1985-07-02 | Procedimiento para la obtencion de la 1-(n-(1(r,s)-(etoxi- carbonil)-3-fenilpropil)-l-alanil)-l-prolina |
| DE19853542735 DE3542735A1 (de) | 1985-07-02 | 1985-12-03 | Verfahren zur herstellung von 1-(n-(1(r,s)-(ethoxycarbonyl)-3-phenylpropyl)-l-alanyl)-l-prolin |
| MX3003A MX162827B (es) | 1985-07-02 | 1986-07-02 | Procedimiento para la obtencion de la 1-(n-(1(r,s)-(etoxicarbonil)-3-fenilpropil)-l-alanil)-l-prolina |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES544781A ES8604609A1 (es) | 1985-07-02 | 1985-07-02 | Procedimiento para la obtencion de la 1-(n-(1(r,s)-(etoxi- carbonil)-3-fenilpropil)-l-alanil)-l-prolina |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ES544781A0 ES544781A0 (es) | 1986-02-01 |
| ES8604609A1 true ES8604609A1 (es) | 1986-02-01 |
Family
ID=8489450
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES544781A Expired ES8604609A1 (es) | 1985-07-02 | 1985-07-02 | Procedimiento para la obtencion de la 1-(n-(1(r,s)-(etoxi- carbonil)-3-fenilpropil)-l-alanil)-l-prolina |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE3542735A1 (es) |
| ES (1) | ES8604609A1 (es) |
| MX (1) | MX162827B (es) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5312831A (en) * | 1993-05-12 | 1994-05-17 | American Cyanamid Company | Urethanes and ureas that induce cytokine production |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL58849A (en) * | 1978-12-11 | 1983-03-31 | Merck & Co Inc | Carboxyalkyl dipeptides and derivatives thereof,their preparation and pharmaceutical compositions containing them |
-
1985
- 1985-07-02 ES ES544781A patent/ES8604609A1/es not_active Expired
- 1985-12-03 DE DE19853542735 patent/DE3542735A1/de not_active Ceased
-
1986
- 1986-07-02 MX MX3003A patent/MX162827B/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES544781A0 (es) | 1986-02-01 |
| MX162827B (es) | 1991-06-28 |
| DE3542735A1 (de) | 1987-01-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PC1A | Transfer granted | ||
| PC1A | Transfer granted | ||
| FD1A | Patent lapsed |
Effective date: 20051018 |