HUP0204450A2 - Eljárás (R)-2-bróm-3-fenil-propionsav előállítására - Google Patents
Eljárás (R)-2-bróm-3-fenil-propionsav előállításáraInfo
- Publication number
- HUP0204450A2 HUP0204450A2 HU0204450A HUP0204450A HUP0204450A2 HU P0204450 A2 HUP0204450 A2 HU P0204450A2 HU 0204450 A HU0204450 A HU 0204450A HU P0204450 A HUP0204450 A HU P0204450A HU P0204450 A2 HUP0204450 A2 HU P0204450A2
- Authority
- HU
- Hungary
- Prior art keywords
- bromo
- bromide
- phenylpropionic acid
- amount
- preparation
- Prior art date
Links
- WDRSCFNERFONKU-MRVPVSSYSA-N (2r)-2-bromo-3-phenylpropanoic acid Chemical compound OC(=O)[C@H](Br)CC1=CC=CC=C1 WDRSCFNERFONKU-MRVPVSSYSA-N 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- COLNVLDHVKWLRT-MRVPVSSYSA-N D-phenylalanine Chemical compound OC(=O)[C@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-MRVPVSSYSA-N 0.000 abstract 3
- 229930182832 D-phenylalanine Natural products 0.000 abstract 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- UOVSNFYJYANSNI-JTQLQIEISA-N (2s)-2-acetylsulfanyl-3-phenylpropanoic acid Chemical compound CC(=O)S[C@H](C(O)=O)CC1=CC=CC=C1 UOVSNFYJYANSNI-JTQLQIEISA-N 0.000 abstract 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 abstract 2
- 239000005541 ACE inhibitor Substances 0.000 abstract 1
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- LVRLSYPNFFBYCZ-VGWMRTNUSA-N omapatrilat Chemical compound C([C@H](S)C(=O)N[C@H]1CCS[C@H]2CCC[C@H](N2C1=O)C(=O)O)C1=CC=CC=C1 LVRLSYPNFFBYCZ-VGWMRTNUSA-N 0.000 abstract 1
- 229950000973 omapatrilat Drugs 0.000 abstract 1
- 150000007530 organic bases Chemical class 0.000 abstract 1
- 235000010288 sodium nitrite Nutrition 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/20—Esters of monothiocarboxylic acids
- C07C327/32—Esters of monothiocarboxylic acids having sulfur atoms of esterified thiocarboxyl groups bound to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
-
- 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
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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
A találmány tárgya: eljárás (R)-2-bróm-3-fenil-propionsavelőállítására D-fenil-alaninból, nátrium-nitritből és HBr-bőlkiindulva vizes oldatban. A reakciót egy bromid jelenlétében, -10 °Cés +30 °C közötti hőmérsékleten hajtják végre. A /HBr + bromid/összmennyiség 3-10 egyenérték - előnyösen 4-8 egyenérték - a D-fenil-alanin mennyiségéhez viszonyítva, míg a bromid mennyisége 0,5-7egyenérték a D-fenil-alanin mennyiségéhez viszonyítva. A bromidotelőnyösen in situ képezik HBr-ből és egy bázisból, pl. KOH-ból vagyNaOH-ból kiindulva. Az (R)-2-bróm-3-fenil-propionsavat ezutánelőnyösen (S)-2-acetil-tio-3-fenil-propionsavvá alakítják áttioecetsav és egy szerves bázis, pl. trietil-amin alkalmazásával. Akapott (S)-2-acetil-tio-3-fenil-propionsav gyógyszerré, különösen ACE-gátlóvá (amilyen omapatrilát) alakítható. Ó
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL1014353A NL1014353C2 (nl) | 2000-02-11 | 2000-02-11 | Werkwijze voor de bereiding van (R) -2-broom-3-fenylpropaanzuur. |
| PCT/NL2001/000079 WO2001058837A2 (en) | 2000-02-11 | 2001-02-02 | Process for the preparation of (r)-2-bromo-3-phenyl-propionic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HUP0204450A2 true HUP0204450A2 (hu) | 2003-04-28 |
Family
ID=19770797
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU0204450A HUP0204450A2 (hu) | 2000-02-11 | 2001-02-02 | Eljárás (R)-2-bróm-3-fenil-propionsav előállítására |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20030125575A1 (hu) |
| EP (1) | EP1272452A2 (hu) |
| JP (1) | JP2003522746A (hu) |
| CN (1) | CN1416414A (hu) |
| AU (1) | AU2001237791A1 (hu) |
| CA (1) | CA2399515A1 (hu) |
| CZ (1) | CZ20022709A3 (hu) |
| HU (1) | HUP0204450A2 (hu) |
| NL (1) | NL1014353C2 (hu) |
| WO (1) | WO2001058837A2 (hu) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10212198A1 (de) * | 2002-03-19 | 2003-10-02 | Aventis Pharma Gmbh | Ethan-1-diaminium-bis(2R)-2-brom-3-phenylpropanoat), Verfahren zu dessen Herstellung und dessen Verwendung |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5508272A (en) * | 1993-06-15 | 1996-04-16 | Bristol-Myers Squibb Company | Compounds containing a fused bicycle ring and processes therefor |
| IT1298268B1 (it) * | 1998-02-18 | 1999-12-20 | Zambon Spa | Procedimento per la preparazione dell'acido (s)-2-bromo-3-fenil- propionico |
| ATE288922T1 (de) * | 1998-04-23 | 2005-02-15 | Novartis Pharma Gmbh | Bestimmte heteroaryl substituierte thiol inhibitoren von endothelin wechselnden enzymen |
-
2000
- 2000-02-11 NL NL1014353A patent/NL1014353C2/nl not_active IP Right Cessation
-
2001
- 2001-02-02 AU AU2001237791A patent/AU2001237791A1/en not_active Abandoned
- 2001-02-02 US US10/203,694 patent/US20030125575A1/en not_active Abandoned
- 2001-02-02 EP EP01910211A patent/EP1272452A2/en not_active Withdrawn
- 2001-02-02 JP JP2001558390A patent/JP2003522746A/ja active Pending
- 2001-02-02 CZ CZ20022709A patent/CZ20022709A3/cs unknown
- 2001-02-02 HU HU0204450A patent/HUP0204450A2/hu unknown
- 2001-02-02 CA CA002399515A patent/CA2399515A1/en not_active Abandoned
- 2001-02-02 CN CN01804766A patent/CN1416414A/zh active Pending
- 2001-02-02 WO PCT/NL2001/000079 patent/WO2001058837A2/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP1272452A2 (en) | 2003-01-08 |
| WO2001058837A3 (en) | 2002-02-28 |
| CA2399515A1 (en) | 2001-08-16 |
| WO2001058837A2 (en) | 2001-08-16 |
| CZ20022709A3 (cs) | 2002-11-13 |
| AU2001237791A1 (en) | 2001-08-20 |
| CN1416414A (zh) | 2003-05-07 |
| US20030125575A1 (en) | 2003-07-03 |
| NL1014353C2 (nl) | 2001-08-15 |
| JP2003522746A (ja) | 2003-07-29 |
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