AU567797B2 - S-(-)-celiprolol - Google Patents
S-(-)-celiprololInfo
- Publication number
- AU567797B2 AU567797B2 AU39722/85A AU3972285A AU567797B2 AU 567797 B2 AU567797 B2 AU 567797B2 AU 39722/85 A AU39722/85 A AU 39722/85A AU 3972285 A AU3972285 A AU 3972285A AU 567797 B2 AU567797 B2 AU 567797B2
- Authority
- AU
- Australia
- Prior art keywords
- pharmaceutically acceptable
- diethylurea
- acetyl
- phenyl
- formula
- 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.)
- Ceased
Links
- 150000003839 salts Chemical class 0.000 abstract 6
- 239000002253 acid Substances 0.000 abstract 4
- JOATXPAWOHTVSZ-UHFFFAOYSA-N Celiprolol Chemical compound CCN(CC)C(=O)NC1=CC=C(OCC(O)CNC(C)(C)C)C(C(C)=O)=C1 JOATXPAWOHTVSZ-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 239000002585 base Substances 0.000 abstract 1
- 238000001640 fractional crystallisation Methods 0.000 abstract 1
- 239000012458 free base Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
- A61P9/06—Antiarrhythmics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/32—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
- C07C275/34—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms having nitrogen atoms of urea groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Heart & Thoracic Surgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pulmonology (AREA)
- Cardiology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Saccharide Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Epoxy Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
1. Claims (for the Contracting States : BE, CH, DE, FR, GB, IT, LI, LU, NL, SE) S(-)-3-[3-acetyl-4-(3-tert.butylamino-2-hydroxypropoxy) phenyl]-1,1-diethylurea (S(-)-celiprolol) and its pharmaceutically acceptable acid addition salts. 1. Claims (for the Contracting State AT) Process for the preparation of S(-)-3-[3-acetyl-4-(3-tert.butylamino-2-hydroxypropoxy) phenyl]-1,1-diethylurea (S(-)-celiprolol) and its pharmaceutically acceptable acid addition salts, characterised in that a) the racemate of the formula see diagramm : EP0155518,P10,F1 in the form of the base is reacted with an enantiomer of a chiral resolving acid in a suitable organic solvent, the mixture of the two diastereomeric salts formed in this manner is separated by fractional crystallisation, and, after separating each diastereomeric salt which contains the laevorotatory enantiomer of the compound of the formula I in the S configuration, is reconverted into the free base or a pharmaceutically acceptable addition salt and the resolving acid is recovered, or b) S(+)-3-[3-acetyl-4-(2,3-epoxypropoxy)-phenyl]- 1,1-diethylurea of the formula see diagramm : EP0155518,P10,F2 is reacted with tertiary butylamine in the presence of water at room temperature or with gentle heating to a maximum of 40 degrees C, and then the laevorotatory enantiomer of the compound of the formula I thus obtained is converted as required into a pharmaceutically acceptable addition salt.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843410380 DE3410380A1 (en) | 1984-03-21 | 1984-03-21 | S (-) - CELIPROLOL, THEIR PHARMACEUTICALLY COMPATIBLE SALT, METHOD FOR THE PRODUCTION THEREOF, USE IN THERAPY AND PHARMACEUTICAL PREPARATIONS |
| DE3410380 | 1984-03-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU3972285A AU3972285A (en) | 1985-09-26 |
| AU567797B2 true AU567797B2 (en) | 1987-12-03 |
Family
ID=6231193
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU39722/85A Ceased AU567797B2 (en) | 1984-03-21 | 1985-03-11 | S-(-)-celiprolol |
Country Status (21)
| Country | Link |
|---|---|
| EP (1) | EP0155518B1 (en) |
| JP (1) | JPS60209557A (en) |
| AT (1) | ATE45945T1 (en) |
| AU (1) | AU567797B2 (en) |
| CA (1) | CA1236116A (en) |
| CS (2) | CS250682B2 (en) |
| DD (2) | DD232489A1 (en) |
| DE (2) | DE3410380A1 (en) |
| DK (1) | DK124585A (en) |
| ES (1) | ES541424A0 (en) |
| FI (1) | FI83636C (en) |
| GR (1) | GR850496B (en) |
| HU (1) | HU193596B (en) |
| IL (1) | IL74383A (en) |
| NO (1) | NO161254C (en) |
| PL (2) | PL143883B1 (en) |
| PT (1) | PT80135B (en) |
| RO (2) | RO91352B (en) |
| SU (2) | SU1333235A3 (en) |
| YU (2) | YU45707B (en) |
| ZA (1) | ZA852086B (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3636209A1 (en) * | 1986-10-24 | 1988-04-28 | Lentia Gmbh | METHOD FOR PRODUCING A BINDER-FREE TABLET-TABLE CELIPROLOL HYDROCHLORIDE GRANULATE |
| AT388099B (en) * | 1986-11-26 | 1989-04-25 | Chemie Holding Ag | Process for the production of solid pharmaceutical forms of 3-(3-acetyl-4-(3-tert-butylamino-2- hydroxypropoxy)phenyl)-1,1-diethylurea hydrochloride |
| US4931557A (en) * | 1988-10-17 | 1990-06-05 | Eli Lilly And Company | Method of resolving cis 3-amino-4-(2-furyl)vinyl)-1-methoxycarbonylmethyl-azetidin-2-one and di-p-toluoyl-tartaric acid salts thereof |
| EP0423484B1 (en) * | 1989-10-16 | 1993-11-03 | PCD-Polymere Gesellschaft m.b.H. | Tablet with sustained release |
| DE3935736A1 (en) * | 1989-10-27 | 1991-05-02 | Chemie Linz Deutschland | Pressed article for sustained pharmaceutical release - contg. poly-lactic acid and polymer of D-3-hydroxybutyric acid, providing good flow properties and easy compression |
| US5227526A (en) * | 1992-06-16 | 1993-07-13 | Mallinckrodt Specialty Chemicals Company | Resolution of 3-dimethylamino-2-methylpropiophenone (3-DAMP) |
| CN101239937B (en) * | 2007-02-07 | 2010-05-19 | 上海雅本化学有限公司 | Method for preparing optical activity R-(-)-1-benzylcarbonyl-3-aminopyrrolidine and hydrochloride thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2458624A1 (en) * | 1973-12-20 | 1975-07-03 | Lentia Gmbh | 3-(4-Ureido-2-acylphenoxy)-2-hydroxy-propylamines - cardioselective beta-adrenergic blocking agents |
| AU7653874A (en) * | 1973-12-20 | 1976-06-17 | Rorer International (Overseas) Inc. | N-[3-alkanoyl-4-(3-amino-2-hydroxy) propoxy-phenyl] ureas, methods for their preparation and compositions containing them |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU170677B (en) * | 1973-12-21 | 1977-08-28 | ||
| US4470965A (en) * | 1982-10-27 | 1984-09-11 | Usv Pharmaceutical Corporation | Celiprolol for the treatment of glaucoma |
-
1984
- 1984-03-21 DE DE19843410380 patent/DE3410380A1/en not_active Withdrawn
-
1985
- 1985-02-19 IL IL74383A patent/IL74383A/en unknown
- 1985-02-20 DE DE8585101802T patent/DE3572656D1/en not_active Expired
- 1985-02-20 AT AT85101802T patent/ATE45945T1/en not_active IP Right Cessation
- 1985-02-20 EP EP85101802A patent/EP0155518B1/en not_active Expired
- 1985-02-21 CA CA000474847A patent/CA1236116A/en not_active Expired
- 1985-02-27 GR GR850496A patent/GR850496B/el unknown
- 1985-03-01 NO NO850834A patent/NO161254C/en unknown
- 1985-03-04 FI FI850860A patent/FI83636C/en not_active IP Right Cessation
- 1985-03-11 AU AU39722/85A patent/AU567797B2/en not_active Ceased
- 1985-03-14 SU SU853866301A patent/SU1333235A3/en active
- 1985-03-14 SU SU853865408A patent/SU1309908A3/en active
- 1985-03-15 RO RO118006A patent/RO91352B/en unknown
- 1985-03-15 RO RO118007A patent/RO91353B/en unknown
- 1985-03-19 YU YU44485A patent/YU45707B/en unknown
- 1985-03-19 DD DD85274250A patent/DD232489A1/en not_active IP Right Cessation
- 1985-03-19 DD DD85274249A patent/DD234860A1/en not_active IP Right Cessation
- 1985-03-19 CS CS851925A patent/CS250682B2/en unknown
- 1985-03-19 CS CS851926A patent/CS250683B2/en unknown
- 1985-03-19 YU YU443/85A patent/YU45246B/en unknown
- 1985-03-20 JP JP60054712A patent/JPS60209557A/en active Pending
- 1985-03-20 DK DK124585A patent/DK124585A/en not_active Application Discontinuation
- 1985-03-20 PL PL1985252463A patent/PL143883B1/en unknown
- 1985-03-20 PL PL25246285A patent/PL252462A1/en unknown
- 1985-03-20 ZA ZA852086A patent/ZA852086B/en unknown
- 1985-03-20 ES ES541424A patent/ES541424A0/en active Granted
- 1985-03-20 PT PT80135A patent/PT80135B/en not_active IP Right Cessation
- 1985-03-21 HU HU851046A patent/HU193596B/en not_active IP Right Cessation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2458624A1 (en) * | 1973-12-20 | 1975-07-03 | Lentia Gmbh | 3-(4-Ureido-2-acylphenoxy)-2-hydroxy-propylamines - cardioselective beta-adrenergic blocking agents |
| AU7653874A (en) * | 1973-12-20 | 1976-06-17 | Rorer International (Overseas) Inc. | N-[3-alkanoyl-4-(3-amino-2-hydroxy) propoxy-phenyl] ureas, methods for their preparation and compositions containing them |
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