ATE351T1 - PHENYLALKYLAMINOAETHYLSALICYLAMIDE DERIVATIVE, ITS PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING IT. - Google Patents
PHENYLALKYLAMINOAETHYLSALICYLAMIDE DERIVATIVE, ITS PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING IT.Info
- Publication number
- ATE351T1 ATE351T1 AT79103473T AT79103473T ATE351T1 AT E351 T1 ATE351 T1 AT E351T1 AT 79103473 T AT79103473 T AT 79103473T AT 79103473 T AT79103473 T AT 79103473T AT E351 T1 ATE351 T1 AT E351T1
- Authority
- AT
- Austria
- Prior art keywords
- acid addition
- optical isomer
- phenylalkylaminoaethylsalicylamide
- derivative
- preparation
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 230000003287 optical effect Effects 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- SGUAFYQXFOLMHL-UHFFFAOYSA-N 2-hydroxy-5-{1-hydroxy-2-[(4-phenylbutan-2-yl)amino]ethyl}benzamide Chemical compound C=1C=C(O)C(C(N)=O)=CC=1C(O)CNC(C)CCC1=CC=CC=C1 SGUAFYQXFOLMHL-UHFFFAOYSA-N 0.000 abstract 2
- 229960001632 labetalol Drugs 0.000 abstract 2
- 206010020772 Hypertension Diseases 0.000 abstract 1
- SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 230000002349 favourable effect Effects 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 125000006239 protecting group Chemical group 0.000 abstract 1
- 229960000581 salicylamide Drugs 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
- A61K31/166—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the carbon of a carboxamide group directly attached to the aromatic ring, e.g. procainamide, procarbazine, metoclopramide, labetalol
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
-
- 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
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/65—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
-
- 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
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Ophthalmology & Optometry (AREA)
- Vascular Medicine (AREA)
- Rheumatology (AREA)
- Urology & Nephrology (AREA)
- Epidemiology (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)
- Medicinal Preparation (AREA)
- Epoxy Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The (R,R) optical isomer of labetalol, namely 5-[ (R)-1-hydroxy- 2-[(R)-1-methyl- 3-phenylpropyl)amino ]ethyl]salicylamide, and its pharmaceutically acceptable acid addition salts, in a state substantially free of the corresponding (R,S), (S,R) and (S,S) optical isomers, are novel compounds with favourable therapeutic properties in comparison with labetalol. They can be used in particular in the treatment of hypertension. The novel (R,R) optical isomer and its pharmaceutically acceptable acid addition salts can be prepared by removal of the protecting groups from an N,O-protected (R,R) optical isomer or acid addition salt thereof, wherein the basic nitrogen atom and the phenolic hydroxy group are protected, preferably by hydrogenolytic removal of hydrogenolysable groups.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US94451678A | 1978-09-20 | 1978-09-20 | |
| EP79103473A EP0009702B1 (en) | 1978-09-20 | 1979-09-17 | A phenylalkylaminoethylsalicylamide, its preparation and pharmaceutical compositions containing it |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ATE351T1 true ATE351T1 (en) | 1981-11-15 |
Family
ID=25481553
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT79103473T ATE351T1 (en) | 1978-09-20 | 1979-09-17 | PHENYLALKYLAMINOAETHYLSALICYLAMIDE DERIVATIVE, ITS PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING IT. |
Country Status (27)
| Country | Link |
|---|---|
| EP (1) | EP0009702B1 (en) |
| JP (3) | JPS5555147A (en) |
| KR (2) | KR830000904A (en) |
| AT (1) | ATE351T1 (en) |
| AU (1) | AU528626B2 (en) |
| CA (1) | CA1151211A (en) |
| CY (1) | CY1175A (en) |
| DD (1) | DD150457A5 (en) |
| DE (1) | DE2961263D1 (en) |
| DK (1) | DK387579A (en) |
| FI (1) | FI792884A7 (en) |
| GR (1) | GR73179B (en) |
| HK (1) | HK13383A (en) |
| HU (1) | HU185523B (en) |
| IE (1) | IE49301B1 (en) |
| IL (1) | IL58258A (en) |
| KE (1) | KE3283A (en) |
| MY (1) | MY8500042A (en) |
| NO (1) | NO149660C (en) |
| NZ (1) | NZ191589A (en) |
| OA (1) | OA06339A (en) |
| PH (1) | PH16794A (en) |
| PL (1) | PL129114B1 (en) |
| PT (1) | PT70191A (en) |
| SG (1) | SG283G (en) |
| YU (1) | YU227379A (en) |
| ZA (1) | ZA794872B (en) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4658060A (en) * | 1982-04-26 | 1987-04-14 | Schering Corporation | Preparation of (-)-5-(beta)-1-hydroxy-2-((beta)-1-methyl-3-phenylpropyl)aminoethyl) salicylamide |
| IT1194406B (en) * | 1983-09-27 | 1988-09-22 | Scharper S P A | PROCEDURE FOR THE PREPARATION OF 2-HYDROXY-5-01-HYDROXY-2 - ((4-FENYL-2-BUTYL) AMINO) ETHYL BENZAMIDE |
| HU190867B (en) * | 1984-01-20 | 1986-11-28 | Egyt Gyogyszervegyeszeti Gyar,Hu | Process for preparing 2-hydroxy-5-/1-hydroxy-2-/1-methyl-3-phenyl-propyl/-amino/ethyl/-benzamide and pharmaceutically acceptable salts thereof |
| US4788183A (en) * | 1987-11-30 | 1988-11-29 | Schering Corporation | Method for treatment of dyslipidemia in humans |
| US4879233A (en) * | 1989-02-10 | 1989-11-07 | Schering Corporation | Novel Aspergillus niveus microorganism used for the chiral reduction of carbonyl groups |
| US6001884A (en) * | 1991-08-23 | 1999-12-14 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| ES2256370T3 (en) * | 1991-08-23 | 2006-07-16 | Nps Pharmaceuticals, Inc. | ACTIVE MOLECULES FOR THE CALCIUM RECEIVER. |
| US5688938A (en) * | 1991-08-23 | 1997-11-18 | The Brigham & Women's Hospital, Inc. | Calcium receptor-active molecules |
| US5763569A (en) * | 1991-08-23 | 1998-06-09 | The Brigham And Women's Hospital, Inc | Calcium receptor-active molecules |
| US6011068A (en) * | 1991-08-23 | 2000-01-04 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| US6313146B1 (en) | 1991-08-23 | 2001-11-06 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| US6031003A (en) * | 1991-08-23 | 2000-02-29 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| US5858684A (en) * | 1991-08-23 | 1999-01-12 | The Brigham And Women's Hospital, Inc. | Method of screening calcium receptor-active molecules |
| US5962314A (en) * | 1993-02-23 | 1999-10-05 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| CN1147459C (en) | 1994-10-21 | 2004-04-28 | Nps药物有限公司 | Calcium Receptor Active Compounds |
| ATE430123T1 (en) | 1996-05-01 | 2009-05-15 | Nps Pharma Inc | INORGANIC COMPOUNDS ACTIVE ON THE ION RECEPTOR |
| IT1313583B1 (en) | 1999-07-30 | 2002-09-09 | Chiesi Farma Spa | 2-AMINOTETRALINIC DERIVATIVES FOR GLAUCOMA THERAPY. |
| PT1961735E (en) * | 2007-02-22 | 2009-12-21 | Indena Spa | Process for the preparation of (2r,3s)-3-phenylisoserine methyl ester acetate salt |
| WO2012021629A2 (en) | 2010-08-11 | 2012-02-16 | Philadelphia Health & Education Corporation | Novel d3 dopamine receptor agonists to treat dyskinesia in parkinson's disease |
| US20190030114A1 (en) * | 2014-11-11 | 2019-01-31 | Western University Of Health Sciences | Isoform-specific calpain inhibitors, methods of identification, and uses thereof |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4012444A (en) * | 1969-07-08 | 1977-03-15 | Allen & Hanburys Limited | 5-[1-Hydroxy-2-(1-methyl-3-phenylpropyl)aminoethyl] salicylamide and physiologically acceptable acid addition salts thereof |
| GB1266058A (en) * | 1969-07-08 | 1972-03-08 | ||
| GB1541933A (en) * | 1975-04-17 | 1979-03-14 | Scherico Ltd | Pharmaceutical compositions containing a diastereoisomer of a phenylalkylaminoethanol derivative |
-
1979
- 1979-09-13 ZA ZA00794872A patent/ZA794872B/en unknown
- 1979-09-17 NO NO792993A patent/NO149660C/en unknown
- 1979-09-17 CY CY1175A patent/CY1175A/en unknown
- 1979-09-17 AU AU50881/79A patent/AU528626B2/en not_active Ceased
- 1979-09-17 EP EP79103473A patent/EP0009702B1/en not_active Expired
- 1979-09-17 DK DK387579A patent/DK387579A/en not_active Application Discontinuation
- 1979-09-17 FI FI792884A patent/FI792884A7/en not_active Application Discontinuation
- 1979-09-17 NZ NZ191589A patent/NZ191589A/en unknown
- 1979-09-17 DE DE7979103473T patent/DE2961263D1/en not_active Expired
- 1979-09-17 AT AT79103473T patent/ATE351T1/en not_active IP Right Cessation
- 1979-09-17 PH PH23042A patent/PH16794A/en unknown
- 1979-09-18 CA CA000335885A patent/CA1151211A/en not_active Expired
- 1979-09-18 IE IE1770/79A patent/IE49301B1/en unknown
- 1979-09-18 OA OA56898A patent/OA06339A/en unknown
- 1979-09-18 JP JP11996879A patent/JPS5555147A/en active Granted
- 1979-09-18 YU YU02273/79A patent/YU227379A/en unknown
- 1979-09-18 PT PT70191A patent/PT70191A/en unknown
- 1979-09-18 IL IL58258A patent/IL58258A/en unknown
- 1979-09-18 GR GR60059A patent/GR73179B/el unknown
- 1979-09-18 KR KR1019790003218A patent/KR830000904A/en not_active Ceased
- 1979-09-19 PL PL1979218408A patent/PL129114B1/en unknown
- 1979-09-19 DD DD79215640A patent/DD150457A5/en unknown
- 1979-09-19 HU HU79SCHE690A patent/HU185523B/en unknown
-
1983
- 1983-01-04 SG SG2/83A patent/SG283G/en unknown
- 1983-04-21 HK HK133/83A patent/HK13383A/en unknown
- 1983-04-25 KE KE3283A patent/KE3283A/en unknown
- 1983-11-17 JP JP58217073A patent/JPS59108749A/en active Pending
-
1984
- 1984-04-09 KR KR1019840001867A patent/KR890001998B1/en not_active Expired
-
1985
- 1985-12-30 MY MY42/85A patent/MY8500042A/en unknown
-
1989
- 1989-11-13 JP JP1292552A patent/JPH02167253A/en active Pending
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| UEP | Publication of translation of european patent specification | ||
| REN | Ceased due to non-payment of the annual fee |