CH546227A - 1-(2-nitrilophenoxy)-2-hydroxy-3-ethylamino - propane - Google Patents
1-(2-nitrilophenoxy)-2-hydroxy-3-ethylamino - propaneInfo
- Publication number
- CH546227A CH546227A CH546227DA CH546227A CH 546227 A CH546227 A CH 546227A CH 546227D A CH546227D A CH 546227DA CH 546227 A CH546227 A CH 546227A
- Authority
- CH
- Switzerland
- Prior art keywords
- cpd
- corresp
- reacting
- hydrolysing
- protecting
- Prior art date
Links
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N dimethylmethane Natural products CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 title 1
- 239000001294 propane Substances 0.000 title 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 abstract 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 2
- ZWAVGZYKJNOTPX-UHFFFAOYSA-N 1,3-diethylurea Chemical compound CCNC(=O)NCC ZWAVGZYKJNOTPX-UHFFFAOYSA-N 0.000 abstract 1
- JFUBFTVIDOXELL-UHFFFAOYSA-N 2-(3-amino-2-hydroxypropoxy)benzonitrile Chemical compound NCC(O)COC1=CC=CC=C1C#N JFUBFTVIDOXELL-UHFFFAOYSA-N 0.000 abstract 1
- 208000001871 Tachycardia Diseases 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000000129 anionic group Chemical group 0.000 abstract 1
- 206010003119 arrhythmia Diseases 0.000 abstract 1
- 239000004202 carbamide Substances 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 208000019622 heart disease Diseases 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 238000011321 prophylaxis Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 230000006794 tachycardia Effects 0.000 abstract 1
- 238000011282 treatment Methods 0.000 abstract 1
Classifications
-
- 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
- A61K31/275—Nitriles; Isonitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/53—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and hydroxy groups bound to the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The title cpd. and its optical isomers and acid addn. salts have beta-adrenolytic activity and may be used for treatment or prophylaxis of heart diseases and arrythmia, esp. tachycardia. They may be prepd. (a) by reacting a cpd. (II): (where Z = or CHOH-CH2Hal) with N,N'-diethyl-urea, (b) reacting (II) with ethylamine, (c) reacting 3-(o-cyanophenoxy)-2-hydroxypropylamine with a cpd. C2H5X (where is a labile anionic gp). (d) replacing the protecting gp. of the corresp. protected -OH cpd. by H, (e) hydrolysing 3-ethyl-5-(2-cyanophenoxymethyl)-oxazolidinone-(2), (f) hydrolysing or pyrolysing the corresp. urea deriv. (g) splitting off the protecting gp. from the corresp. N-protected cpd. (h) converting a ring substituent into a cyano gp.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1940566A DE1940566C3 (en) | 1969-08-08 | 1969-08-08 | 1- (2-Nitrilophenoxy) -2-hydroxy-3ethylaminopropane, process for its preparation and pharmaceuticals containing it |
| CH116873 | 1970-08-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH546227A true CH546227A (en) | 1974-02-28 |
Family
ID=25686873
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH546227D CH546227A (en) | 1969-08-08 | 1970-08-05 | 1-(2-nitrilophenoxy)-2-hydroxy-3-ethylamino - propane |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH546227A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0035733A1 (en) * | 1980-03-08 | 1981-09-16 | C.H. Boehringer Sohn | 1-(Acylamino-aryloxy-)2-hydroxy-3-alkinyl-amino propanes and processes for their manufacture |
| EP0035734A1 (en) * | 1980-03-08 | 1981-09-16 | C.H. Boehringer Sohn | 1-(Acylamino-aryloxy-)2-hydroxy-3-alkinyl-amino propanes and processes for their manufacture |
-
1970
- 1970-08-05 CH CH546227D patent/CH546227A/en not_active IP Right Cessation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0035733A1 (en) * | 1980-03-08 | 1981-09-16 | C.H. Boehringer Sohn | 1-(Acylamino-aryloxy-)2-hydroxy-3-alkinyl-amino propanes and processes for their manufacture |
| EP0035734A1 (en) * | 1980-03-08 | 1981-09-16 | C.H. Boehringer Sohn | 1-(Acylamino-aryloxy-)2-hydroxy-3-alkinyl-amino propanes and processes for their manufacture |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |