AR044018A1 - Procedimiento para la sintesis del acido (2s,3as,7as)-perhidroindol-2-carboxilico y esteres del mismo, y aplicacion en la sintesis de perindopril - Google Patents
Procedimiento para la sintesis del acido (2s,3as,7as)-perhidroindol-2-carboxilico y esteres del mismo, y aplicacion en la sintesis de perindoprilInfo
- Publication number
- AR044018A1 AR044018A1 ARP040101247A ARP040101247A AR044018A1 AR 044018 A1 AR044018 A1 AR 044018A1 AR P040101247 A ARP040101247 A AR P040101247A AR P040101247 A ARP040101247 A AR P040101247A AR 044018 A1 AR044018 A1 AR 044018A1
- Authority
- AR
- Argentina
- Prior art keywords
- formula
- compound
- synthesis
- defined above
- linear
- Prior art date
Links
- 230000015572 biosynthetic process Effects 0.000 title abstract 5
- 238000003786 synthesis reaction Methods 0.000 title abstract 5
- 238000000034 method Methods 0.000 title abstract 3
- 239000002253 acid Substances 0.000 title abstract 2
- IPVQLZZIHOAWMC-QXKUPLGCSA-N perindopril Chemical compound C1CCC[C@H]2C[C@@H](C(O)=O)N(C(=O)[C@H](C)N[C@@H](CCC)C(=O)OCC)[C@H]21 IPVQLZZIHOAWMC-QXKUPLGCSA-N 0.000 title abstract 2
- 229960002582 perindopril Drugs 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 abstract 2
- 150000003254 radicals Chemical class 0.000 abstract 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical group 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 238000011917 diastereoselective reduction Methods 0.000 abstract 1
- 230000026030 halogenation Effects 0.000 abstract 1
- 238000005658 halogenation reaction Methods 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 239000003999 initiator Substances 0.000 abstract 1
- 229910052740 iodine Chemical group 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 238000007154 radical cyclization reaction Methods 0.000 abstract 1
- 150000003839 salts Chemical class 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- 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
- C07C229/20—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 halogen atoms or by nitro or nitroso 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06026—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atom, i.e. Gly or Ala
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Pharmacology & Pharmacy (AREA)
- Cardiology (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Heart & Thoracic Surgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
Abstract
Procedimiento para la síntesis de compuestos, aplicables en la síntesis de perindopril y sales farmacéuticamente aceptables del mismo. Reivindicación 1: Procedimiento para la síntesis de compuestos de fórmula (1), donde R representa un átomo de hidrógeno o un grupo bencilo o alquilo (C1-6) lineal o ramificado, caracterizado porque la (L)-serina protegida de fórmula (2), donde R1 representa un grupo bencilo o alquilo (C1-6) lineal o ramificado, se condensa con un compuesto de fórmula (3), donde Ar representa un grupo fenilo opcionalmente sustituido por uno o más grupos alquilo (C1-6) lineal o ramificado o un grupo naftilo, para obtener un compuesto de fórmula (4), donde Ar y R1 son tal como se han definido anteriormente, que se somete a reducción diastereoselectiva para obtener un compuesto de fórmula (5), donde Ar y R1 son tal como se han definido anteriormente, que se condensa con ciclohexanona para obtener un compuesto de fórmula (6), donde Ar y R1 son tal como se han definido anteriormente, que se convierte por halogenación en un compuesto de fórmula (7), donde Ar y R1 son tal como se han definido anteriormente y X representa un átomo de cloro, bromo o yodo, que se somete a ciclización de radicales libres por tratamiento con hidruro de n-tributilestaño, en presencia de un iniciador de radicales libres, para obtener un compuesto de fórmula (8), donde Ar y R1 son tal como se han definido anteriormente, la función amina y, si se desea, la función ácido del mismo se desprotegen para obtener el compuesto de fórmula (1).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03290931A EP1354874B1 (fr) | 2003-04-15 | 2003-04-15 | Nouveau procédé de synthèse de l'acide (2s, 3aS, 7aS)-perhydroindole-2-carboxylique et de ses esters, et application a la synthèse du perindopril |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR044018A1 true AR044018A1 (es) | 2005-08-24 |
Family
ID=28459640
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP040101247A AR044018A1 (es) | 2003-04-15 | 2004-04-14 | Procedimiento para la sintesis del acido (2s,3as,7as)-perhidroindol-2-carboxilico y esteres del mismo, y aplicacion en la sintesis de perindopril |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP1354874B1 (es) |
| AR (1) | AR044018A1 (es) |
| AT (1) | ATE283257T1 (es) |
| DE (1) | DE60300166T2 (es) |
| DK (1) | DK1354874T3 (es) |
| ES (1) | ES2233913T3 (es) |
| MY (1) | MY136549A (es) |
| PT (1) | PT1354874E (es) |
| SI (1) | SI1354874T1 (es) |
| WO (1) | WO2004092133A1 (es) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100391945C (zh) * | 2005-05-31 | 2008-06-04 | 浙江大学 | 一种s-(-)-吲哚啉-2-羧酸的合成方法 |
| JP2012533563A (ja) * | 2009-07-16 | 2012-12-27 | アボット ラボラトリーズ | トランドラプリル用の中間体である（２Ｓ，３ａＲ，７ａＳ）−オクタヒドロ−１Ｈ−インドールカルボン酸の合成法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE55867B1 (en) * | 1981-12-29 | 1991-02-14 | Hoechst Ag | New derivatives of bicyclic aminoacids,processes for their preparation,agents containing these compounds and their use,and new bicyclic aminoacids as intermediates and processes for their preparation |
| FR2620703B1 (fr) * | 1987-09-17 | 1991-10-04 | Adir | Procede de synthese industrielle de l'acide perhydroindole carboxylique - 2(2s, 3as, 7as). application a la synthese de carboxyalkyl dipeptides |
-
2003
- 2003-04-15 DE DE60300166T patent/DE60300166T2/de not_active Expired - Lifetime
- 2003-04-15 DK DK03290931T patent/DK1354874T3/da active
- 2003-04-15 EP EP03290931A patent/EP1354874B1/fr not_active Expired - Lifetime
- 2003-04-15 PT PT03290931T patent/PT1354874E/pt unknown
- 2003-04-15 SI SI200330010T patent/SI1354874T1/xx unknown
- 2003-04-15 AT AT03290931T patent/ATE283257T1/de active
- 2003-04-15 ES ES03290931T patent/ES2233913T3/es not_active Expired - Lifetime
-
2004
- 2004-04-07 WO PCT/FR2004/000858 patent/WO2004092133A1/fr not_active Ceased
- 2004-04-14 AR ARP040101247A patent/AR044018A1/es unknown
- 2004-04-15 MY MYPI20041395A patent/MY136549A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MY136549A (en) | 2008-10-31 |
| PT1354874E (pt) | 2005-03-31 |
| ATE283257T1 (de) | 2004-12-15 |
| ES2233913T3 (es) | 2005-06-16 |
| DE60300166T2 (de) | 2005-12-01 |
| WO2004092133A1 (fr) | 2004-10-28 |
| DK1354874T3 (da) | 2005-03-14 |
| EP1354874A1 (fr) | 2003-10-22 |
| SI1354874T1 (en) | 2005-04-30 |
| EP1354874B1 (fr) | 2004-11-24 |
| DE60300166D1 (de) | 2004-12-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FB | Suspension of granting procedure |