GB1535566A - Method for the preparation of optically pure loweralkyl imidazole carboxylates - Google Patents
Method for the preparation of optically pure loweralkyl imidazole carboxylatesInfo
- Publication number
- GB1535566A GB1535566A GB6339/76A GB633976A GB1535566A GB 1535566 A GB1535566 A GB 1535566A GB 6339/76 A GB6339/76 A GB 6339/76A GB 633976 A GB633976 A GB 633976A GB 1535566 A GB1535566 A GB 1535566A
- Authority
- GB
- United Kingdom
- Prior art keywords
- imidazole
- optically active
- phenylethyl
- acid
- loweralkyl
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Optically active C1-C3-alkyl esters of 1-(1-phenylethyl)-1H-imidazole-5-carboxylic acid are prepared by reacting racemic 1-(1-phenylethyl)-1H-imidazole-5-carboxylic acid with an optically active isomer of 1-phenylethylamine, 1-(1-naphthyl)ethylamine or 1-(2-naphthyl)ethylamine. The resulting insoluble diastereomeric salt is separated off and treated with a strong non-oxidising mineral acid. The resulting optically active 1-(1-phenylethyl)-1H-imidazole-5-carboxylic acid is then esterified with a C1-C3-alcohol. In another process, the resulting optically active acid is firstly converted into the acid halide and then correspondingly esterified. The prepared compounds can be used as hypnotics.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US55719475A | 1975-03-10 | 1975-03-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1535566A true GB1535566A (en) | 1978-12-13 |
Family
ID=24224401
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB6339/76A Expired GB1535566A (en) | 1975-03-10 | 1976-02-18 | Method for the preparation of optically pure loweralkyl imidazole carboxylates |
Country Status (27)
| Country | Link |
|---|---|
| JP (1) | JPS51115473A (en) |
| AT (1) | AT353262B (en) |
| AU (1) | AU503733B2 (en) |
| BE (1) | BE839120A (en) |
| BG (1) | BG24806A3 (en) |
| CA (1) | CA1066709A (en) |
| CH (1) | CH629192A5 (en) |
| CS (1) | CS203116B2 (en) |
| DE (1) | DE2609573A1 (en) |
| DK (1) | DK99376A (en) |
| ES (1) | ES445450A1 (en) |
| FI (1) | FI62292C (en) |
| FR (1) | FR2318159A1 (en) |
| GB (1) | GB1535566A (en) |
| HU (1) | HU172026B (en) |
| IE (1) | IE42652B1 (en) |
| IL (1) | IL49190A (en) |
| IT (1) | IT1057941B (en) |
| LU (1) | LU74503A1 (en) |
| NL (1) | NL7602444A (en) |
| NO (1) | NO144884C (en) |
| PL (1) | PL99926B1 (en) |
| PT (1) | PT64879B (en) |
| SE (1) | SE7601959L (en) |
| SU (1) | SU677656A3 (en) |
| YU (1) | YU60876A (en) |
| ZA (1) | ZA761427B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4340598A (en) | 1979-11-12 | 1982-07-20 | Takeda Chemical Industries, Ltd. | Hypotensive imidazole derivatives |
| US4355040A (en) | 1979-11-12 | 1982-10-19 | Takeda Chemical Industries, Ltd. | Hypotensive imidazole-5-acetic acid derivatives |
| US4582847A (en) * | 1982-03-16 | 1986-04-15 | Takeda Chemical Industries, Ltd. | 4-chloro-2-phenylimidazole-5-acetic acid derivatives and use as diuretics and hypotensives |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE871675A (en) * | 1977-12-02 | 1979-04-30 | Smithkline Corp | PROCESS FOR PREPARING DERIVATIVES OF IMIDAZOLE |
| PL149675B1 (en) * | 1986-03-10 | 1990-03-31 | Method of obtaining novel derivatives of 1-methyl 1h-imidazolecarboxylic-5 acid | |
| JP5580287B2 (en) * | 2008-03-31 | 2014-08-27 | ザ ジェネラル ホスピタル コーポレイション | Etomidate analogs with improved pharmacokinetic and pharmacodynamic properties |
| ES2617536T3 (en) | 2012-01-13 | 2017-06-19 | The General Hospital Corporation | Anesthetic compounds and related methods of use |
-
1976
- 1976-02-13 CA CA245,697A patent/CA1066709A/en not_active Expired
- 1976-02-18 GB GB6339/76A patent/GB1535566A/en not_active Expired
- 1976-02-19 SE SE7601959A patent/SE7601959L/en not_active Application Discontinuation
- 1976-02-23 ES ES445450A patent/ES445450A1/en not_active Expired
- 1976-03-01 FR FR7605762A patent/FR2318159A1/en active Granted
- 1976-03-03 BE BE164793A patent/BE839120A/en not_active IP Right Cessation
- 1976-03-05 CH CH280676A patent/CH629192A5/en not_active IP Right Cessation
- 1976-03-08 NO NO760790A patent/NO144884C/en unknown
- 1976-03-08 JP JP51024280A patent/JPS51115473A/en active Pending
- 1976-03-08 DK DK99376*#A patent/DK99376A/en not_active Application Discontinuation
- 1976-03-08 CS CS761495A patent/CS203116B2/en unknown
- 1976-03-08 IT IT48460/76A patent/IT1057941B/en active
- 1976-03-08 DE DE19762609573 patent/DE2609573A1/en not_active Withdrawn
- 1976-03-08 LU LU74503A patent/LU74503A1/xx unknown
- 1976-03-09 FI FI760601A patent/FI62292C/en not_active IP Right Cessation
- 1976-03-09 AU AU11806/76A patent/AU503733B2/en not_active Expired
- 1976-03-09 PT PT64879A patent/PT64879B/en unknown
- 1976-03-09 HU HU76JA00000750A patent/HU172026B/en unknown
- 1976-03-09 ZA ZA761427A patent/ZA761427B/en unknown
- 1976-03-09 AT AT171776A patent/AT353262B/en not_active IP Right Cessation
- 1976-03-09 YU YU00608/76A patent/YU60876A/en unknown
- 1976-03-09 IE IE482/76A patent/IE42652B1/en unknown
- 1976-03-09 NL NL7602444A patent/NL7602444A/en not_active Application Discontinuation
- 1976-03-10 SU SU762329945A patent/SU677656A3/en active
- 1976-03-10 BG BG032575A patent/BG24806A3/en unknown
- 1976-03-10 IL IL49190A patent/IL49190A/en unknown
- 1976-03-10 PL PL1976187827A patent/PL99926B1/en unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4340598A (en) | 1979-11-12 | 1982-07-20 | Takeda Chemical Industries, Ltd. | Hypotensive imidazole derivatives |
| US4355040A (en) | 1979-11-12 | 1982-10-19 | Takeda Chemical Industries, Ltd. | Hypotensive imidazole-5-acetic acid derivatives |
| US4582847A (en) * | 1982-03-16 | 1986-04-15 | Takeda Chemical Industries, Ltd. | 4-chloro-2-phenylimidazole-5-acetic acid derivatives and use as diuretics and hypotensives |
Also Published As
| Publication number | Publication date |
|---|---|
| PT64879A (en) | 1976-04-01 |
| BG24806A3 (en) | 1978-05-12 |
| DE2609573A1 (en) | 1976-09-30 |
| ES445450A1 (en) | 1977-10-16 |
| IT1057941B (en) | 1982-03-30 |
| YU60876A (en) | 1983-01-21 |
| NO144884C (en) | 1981-12-02 |
| SU677656A3 (en) | 1979-07-30 |
| CH629192A5 (en) | 1982-04-15 |
| AU1180676A (en) | 1977-09-15 |
| AU503733B2 (en) | 1979-09-20 |
| FI62292C (en) | 1982-12-10 |
| NL7602444A (en) | 1976-09-14 |
| CS203116B2 (en) | 1981-02-27 |
| SE7601959L (en) | 1976-09-13 |
| HU172026B (en) | 1978-05-28 |
| PL99926B1 (en) | 1978-08-31 |
| IE42652L (en) | 1976-09-10 |
| ATA171776A (en) | 1979-04-15 |
| LU74503A1 (en) | 1976-09-01 |
| JPS51115473A (en) | 1976-10-12 |
| FI62292B (en) | 1982-08-31 |
| PT64879B (en) | 1978-02-06 |
| DK99376A (en) | 1976-09-11 |
| NO144884B (en) | 1981-08-24 |
| CA1066709A (en) | 1979-11-20 |
| FI760601A (en) | 1976-09-11 |
| FR2318159A1 (en) | 1977-02-11 |
| IL49190A (en) | 1980-07-31 |
| AT353262B (en) | 1979-11-12 |
| ZA761427B (en) | 1977-10-26 |
| IL49190A0 (en) | 1976-05-31 |
| IE42652B1 (en) | 1980-09-24 |
| FR2318159B1 (en) | 1979-07-27 |
| BE839120A (en) | 1976-09-03 |
| NO760790L (en) | 1976-09-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |