IE52300B1 - New substituted 3-phenoxy-1-alkoxycarbonyl-alkylamino propanol-2-s having beta receptor blocking properties - Google Patents
New substituted 3-phenoxy-1-alkoxycarbonyl-alkylamino propanol-2-s having beta receptor blocking propertiesInfo
- Publication number
- IE52300B1 IE52300B1 IE1207/81A IE120781A IE52300B1 IE 52300 B1 IE52300 B1 IE 52300B1 IE 1207/81 A IE1207/81 A IE 1207/81A IE 120781 A IE120781 A IE 120781A IE 52300 B1 IE52300 B1 IE 52300B1
- Authority
- IE
- Ireland
- Prior art keywords
- compound
- formula
- aminopropanoate
- preparation
- ethyl
- Prior art date
Links
- 230000000903 blocking effect Effects 0.000 title abstract description 5
- 102000012740 beta Adrenergic Receptors Human genes 0.000 title description 2
- 108010079452 beta Adrenergic Receptors Proteins 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 120
- 238000000034 method Methods 0.000 claims abstract description 49
- 238000002360 preparation method Methods 0.000 claims abstract description 33
- 206010000891 acute myocardial infarction Diseases 0.000 claims abstract description 9
- 239000000825 pharmaceutical preparation Substances 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims description 31
- 239000002253 acid Substances 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 25
- 230000008569 process Effects 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 239000002585 base Substances 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 9
- KMYNADRDKARQSO-UHFFFAOYSA-N ethyl 3-[[3-(2-cyanophenoxy)-2-hydroxypropyl]amino]propanoate Chemical compound CCOC(=O)CCNCC(O)COC1=CC=CC=C1C#N KMYNADRDKARQSO-UHFFFAOYSA-N 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 239000012458 free base Substances 0.000 claims description 5
- 238000001990 intravenous administration Methods 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 4
- 230000037396 body weight Effects 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- JGYBUJVSQJIAHT-UHFFFAOYSA-N propyl 3-[[3-(2-cyanophenoxy)-2-hydroxypropyl]amino]propanoate Chemical compound CCCOC(=O)CCNCC(O)COC1=CC=CC=C1C#N JGYBUJVSQJIAHT-UHFFFAOYSA-N 0.000 claims description 4
- 206010061216 Infarction Diseases 0.000 claims description 3
- 241001465754 Metazoa Species 0.000 claims description 3
- WEQFUJZGDTXOHY-UHFFFAOYSA-N ethyl 3-[[2-hydroxy-3-(3-methoxyphenoxy)propyl]amino]propanoate Chemical compound CCOC(=O)CCNCC(O)COC1=CC=CC(OC)=C1 WEQFUJZGDTXOHY-UHFFFAOYSA-N 0.000 claims description 3
- KXHSSASRVUYPEQ-UHFFFAOYSA-N ethyl 3-[[3-(2,3-dimethylphenoxy)-2-hydroxypropyl]amino]propanoate Chemical compound CCOC(=O)CCNCC(O)COC1=CC=CC(C)=C1C KXHSSASRVUYPEQ-UHFFFAOYSA-N 0.000 claims description 3
- YEWBCLAALSDWQB-UHFFFAOYSA-N ethyl 3-[[3-(2-cyano-4-methoxyphenoxy)-2-hydroxypropyl]amino]propanoate Chemical compound CCOC(=O)CCNCC(O)COC1=CC=C(OC)C=C1C#N YEWBCLAALSDWQB-UHFFFAOYSA-N 0.000 claims description 3
- PRANETLWEMLBSV-UHFFFAOYSA-N ethyl 3-[[3-(3-cyanophenoxy)-2-hydroxypropyl]amino]propanoate Chemical compound CCOC(=O)CCNCC(O)COC1=CC=CC(C#N)=C1 PRANETLWEMLBSV-UHFFFAOYSA-N 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 230000007574 infarction Effects 0.000 claims description 3
- 238000001356 surgical procedure Methods 0.000 claims description 3
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000003700 epoxy group Chemical group 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims 1
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- 229940125890 compound Ia Drugs 0.000 claims 1
- 238000003745 diagnosis Methods 0.000 claims 1
- WRBCAUAQHYZFHN-UHFFFAOYSA-N ethyl 3-[[2-hydroxy-3-(3-methylphenoxy)propyl]amino]propanoate Chemical compound CCOC(=O)CCNCC(O)COC1=CC=CC(C)=C1 WRBCAUAQHYZFHN-UHFFFAOYSA-N 0.000 claims 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 230000001131 transforming effect Effects 0.000 claims 1
- 102000015005 beta-adrenergic receptor activity proteins Human genes 0.000 abstract description 10
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- 238000002347 injection Methods 0.000 abstract description 5
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- 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
-
- 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
- C07C275/04—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 acyclic carbon atoms
- C07C275/20—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 acyclic carbon atoms of an unsaturated carbon skeleton
- C07C275/24—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 acyclic carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE8004088A SE8004088L (sv) | 1980-06-02 | 1980-06-02 | Nya substituerade 3-fenoxi-l-alkoxikarbonylalkylamino-propanol-2-er med beta-receptorblockerande egenskaper samt forfarande for deras framstellning, farmaceutiska beredningar innehallande desamma och metod att ... |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE811207L IE811207L (en) | 1981-12-02 |
| IE52300B1 true IE52300B1 (en) | 1987-09-02 |
Family
ID=20341102
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1207/81A IE52300B1 (en) | 1980-06-02 | 1981-05-29 | New substituted 3-phenoxy-1-alkoxycarbonyl-alkylamino propanol-2-s having beta receptor blocking properties |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US5051446A (en, 2012) |
| EP (1) | EP0041492B1 (en, 2012) |
| JP (1) | JPS5724334A (en, 2012) |
| KR (1) | KR850000872B1 (en, 2012) |
| AT (1) | ATE12223T1 (en, 2012) |
| AU (1) | AU549890B2 (en, 2012) |
| CA (1) | CA1167465A (en, 2012) |
| CS (1) | CS404681A2 (en, 2012) |
| DD (1) | DD159329A5 (en, 2012) |
| DE (1) | DE3169348D1 (en, 2012) |
| DK (1) | DK152490C (en, 2012) |
| ES (1) | ES502654A0 (en, 2012) |
| FI (1) | FI73198C (en, 2012) |
| GR (1) | GR75683B (en, 2012) |
| HU (1) | HU184859B (en, 2012) |
| IE (1) | IE52300B1 (en, 2012) |
| MY (1) | MY8600651A (en, 2012) |
| NO (1) | NO162283C (en, 2012) |
| NZ (1) | NZ197238A (en, 2012) |
| PH (1) | PH16848A (en, 2012) |
| PT (1) | PT73112B (en, 2012) |
| SE (1) | SE8004088L (en, 2012) |
| SU (1) | SU1082317A3 (en, 2012) |
| ZA (1) | ZA812983B (en, 2012) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4593119A (en) * | 1980-11-28 | 1986-06-03 | American Hospital Supply Corporation | Method for treatment or prophylaxis of cardiac disorders |
| EP0053434B1 (en) * | 1980-11-28 | 1986-08-27 | American Hospital Supply Corporation | Compounds and method for treatment or prophylaxis of cardiac disorders |
| US4559359A (en) * | 1981-06-23 | 1985-12-17 | American Hospital Supply Corporation | Method for treating glaucoma by the topical administration of selectively metabolized beta-blocking agents |
| US4578403A (en) * | 1981-06-23 | 1986-03-25 | American Hospital Supply Corporation | Method for treating glaucoma by the topical administration of selectively metabolized beta-blocking agents |
| US4454154A (en) * | 1981-06-23 | 1984-06-12 | American Hospital Supply Corporation | Method for treating glaucoma by the topical administration of selectively metabolized beta-blocking agents |
| US4455317A (en) * | 1981-06-23 | 1984-06-19 | American Hospital Supply Corporation | Method for treating glaucoma by the topical administration of selectively metabolized beta-blocking agents |
| CA1211111A (en) * | 1982-02-15 | 1986-09-09 | Isao Yanagisawa | Process for preparing novel pyrimidone compounds |
| DE3475615D1 (en) * | 1983-02-03 | 1989-01-19 | Univ California | Beta-adrenergic antagonist compounds and derivatives of beta-adrenergic antagonists |
| US4687873A (en) * | 1983-02-03 | 1987-08-18 | The Regents Of The University Of California | Derivatives of β-adrenergic antagonists |
| JPS63162660A (ja) * | 1986-12-26 | 1988-07-06 | Toray Ind Inc | 感光性化合物の製造方法 |
| US5256812A (en) * | 1989-01-31 | 1993-10-26 | Hoffmann-La Roche Inc. | Carboxamides and sulfonamides |
| US5084466A (en) * | 1989-01-31 | 1992-01-28 | Hoffmann-La Roche Inc. | Novel carboxamide pyridine compounds which have useful pharmaceutical utility |
| JP3807573B2 (ja) | 1997-11-20 | 2006-08-09 | 住友電気工業株式会社 | ディスクブレーキ用パッド |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB673413A (en) * | 1950-03-22 | 1952-06-04 | Rhone Poulenc Sa | New local anaesthetics which are substituted benzoic esters and processes for making the same |
| NL163775C (nl) * | 1967-12-18 | 1980-10-15 | Boehringer Sohn Ingelheim | Werkwijze ter bereiding van farmaceutische preparaten met beta-receptoren blokkerende werking, alsmede werkwijze ter bereiding van 1-(cyaanfenoxy)-2-hydroxy-3-(sec.alkylamino) propaanderivaten. |
| DE1922003C3 (de) * | 1969-04-30 | 1979-10-11 | Boehringer Mannheim Gmbh, 6800 Mannheim | N-(3-Aryloxy-2-hydroxypropyl)-aminocarbonsäuren, deren Ester, Amide und Salze, Verfahren zur Herstellung dieser Verbindungen und deren Verwendung bei der Bekämpfung von Herzinsuffizienz |
| SE354851B (en, 2012) * | 1970-02-18 | 1973-03-26 | Haessle Ab | |
| FR2132570B1 (en, 2012) * | 1971-04-09 | 1974-08-02 | Lipha | |
| DE2324584A1 (de) * | 1972-06-08 | 1974-01-10 | Ciba Geigy Ag | Neue amine und verfahren zu ihrer herstellung |
| SE386892B (sv) * | 1972-07-06 | 1976-08-23 | Haessle Ab | Forfarande for framstellning av oxaminoforeningar |
| SE388849B (sv) | 1974-02-14 | 1976-10-18 | Haessle Ab | Forfarande for framstellning av nya aminer med beta-receptorstimulerande verkan |
| PT66890B (fr) * | 1976-08-21 | 1979-01-25 | Hexachimie | Procede pour la preparation des aryloxy-1 amino-3 propanol-2 |
| US4450173A (en) * | 1980-11-28 | 1984-05-22 | American Hospital Supply Corporation | Compounds and method for treatment or prophylaxis of cardiac disorders |
| US4387103A (en) * | 1980-11-28 | 1983-06-07 | American Hospital Supply Corporation | Method for treatment or prophylaxis of cardiac disorders |
-
1980
- 1980-06-02 SE SE8004088A patent/SE8004088L/xx not_active Application Discontinuation
-
1981
- 1981-05-05 ZA ZA00812983A patent/ZA812983B/xx unknown
- 1981-05-08 CA CA000377144A patent/CA1167465A/en not_active Expired
- 1981-05-27 DE DE8181850096T patent/DE3169348D1/de not_active Expired
- 1981-05-27 AT AT81850096T patent/ATE12223T1/de not_active IP Right Cessation
- 1981-05-27 NO NO811798A patent/NO162283C/no not_active IP Right Cessation
- 1981-05-27 EP EP81850096A patent/EP0041492B1/en not_active Expired
- 1981-05-28 PH PH25684A patent/PH16848A/en unknown
- 1981-05-29 AU AU71167/81A patent/AU549890B2/en not_active Ceased
- 1981-05-29 IE IE1207/81A patent/IE52300B1/en not_active IP Right Cessation
- 1981-05-29 FI FI811672A patent/FI73198C/fi not_active IP Right Cessation
- 1981-05-29 NZ NZ197238A patent/NZ197238A/en unknown
- 1981-05-30 KR KR1019810001932A patent/KR850000872B1/ko not_active Expired
- 1981-06-01 CS CS814046A patent/CS404681A2/cs unknown
- 1981-06-01 DK DK239481A patent/DK152490C/da active
- 1981-06-01 SU SU813289352A patent/SU1082317A3/ru active
- 1981-06-01 GR GR65115A patent/GR75683B/el unknown
- 1981-06-01 HU HU811623A patent/HU184859B/hu unknown
- 1981-06-01 PT PT73112A patent/PT73112B/pt unknown
- 1981-06-01 DD DD81230465A patent/DD159329A5/de not_active IP Right Cessation
- 1981-06-01 ES ES502654A patent/ES502654A0/es active Granted
- 1981-06-02 JP JP8390481A patent/JPS5724334A/ja active Granted
-
1986
- 1986-12-30 MY MY651/86A patent/MY8600651A/xx unknown
-
1989
- 1989-03-13 US US07/323,194 patent/US5051446A/en not_active Expired - Fee Related
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK9A | Patent expired |