GB1069345A - New alkanolamine derivatives - Google Patents
New alkanolamine derivativesInfo
- Publication number
- GB1069345A GB1069345A GB4716066A GB4716066A GB1069345A GB 1069345 A GB1069345 A GB 1069345A GB 4716066 A GB4716066 A GB 4716066A GB 4716066 A GB4716066 A GB 4716066A GB 1069345 A GB1069345 A GB 1069345A
- Authority
- GB
- United Kingdom
- Prior art keywords
- radical
- alkyl
- substituent
- bears
- radicals
- 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
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D263/06—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by oxygen atoms, attached to ring carbon atoms
-
- 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
- C07D303/36—Compounds containing oxirane rings with hydrocarbon radicals, substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises racemic alkanolamine derivatives of formula <FORM:1069345/C2/1> wherein R1, R3 and R4 represent hydrogen, R2 the n-propyl radical and the radical A represents 3-tolyl, 2,5-dichlorophenyl or 3-methoxyphenyl; or R1 represents hydrogen or an alkyl radical (not more than 5 C), R2 a branched chain alkyl or hydroxyalkyl radical (not more than 10 C), or for an alkyl radical (not more than 5 C), or for a cycloalkyl or alkenyl radical (not more than 15 C) and optionally substituted by one or more halogen atoms, hydroxy radicals, or alkoxy radicals (not more than 5 C), R3 and R4 which may be the same or different represent hydrogen or alkyl radicals (not more than 5 C) and the benzene ring A has a single substituent in the 3- or 4-position only which is an halogen atom, an alkyl, alkoxy, alkylthio, alkanoyl, aralkanoyl, aroyl, aryl, aryloxy, alkylaryloxy, arylthio, arylsulphonyl, arylamino, aralkyl, aralkoxy, or alkenyl radicals (each containing not more than 10 C), a halogenoalkyl radical (not more than 5 C) or an hydroxy or nitro radical, or the benzene ring A bears a single substituent in the 2-position only, which is an hydroxy, nitro, iodo, alkanoyl, aralkanoyl, aroyl, aryl, aryloxy, alkylaryloxy, arylthio, arylsulphonyl, arylamino, aralkyl or aralkoxy substituent (each containing not more than 10 carbon atoms, or the benzene ring A bears two, three, four, or five substituents which are selected from the radicals given for the 3- or 4-position only; the carboxylic esters and the salts thereof, which derivatives possess b -adrenergic blocking activity and are useful in the treatment or prophylaxis of coronary artery disease. Certain listed compounds are excluded from compounds of the above formula and examples of suitable radicals are given. The alkanolamine derivatives are prepared by reacting a halogeno compound <FORM:1069345/C2/2> where Z stands for a Cl, Br or I atom with an amine NHR1R2; by reacting an epoxide <FORM:1069345/C2/3> with an amine NHR1R2; by reacting a compound <FORM:1069345/C2/4> with ZCH.R3.CHOH.CHR4.NR1R2 or <FORM:1069345/C2/5> by the hydrogenolysis of <FORM:1069345/C2/6> where R stands for an hydrogenolysable radical e.g. benzyl and R6 a carbonyl, hydroxymethylene or CHOR1, where R7 represents an hydrogenolysable radical; by reacting an amino derivative <FORM:1069345/C2/7> with a carbonyl compound R8.CO.R9, where R8 represents hydrogen, or alkyl (not more than 4 C) and R9 a branched chain alkyl or hydroxyalkyl or substituted alkyl or aralkyl radical; by the hydrogenolysis of a compound <FORM:1069345/C2/8> where the benzene ring A bears a substituent -OR7 to form compounds in which A bears an hydroxy substituent; by the oxidation of <FORM:1069345/C2/9> wherein A bears an arylthio substituent to produce a derivative wherein the ring A bears an arylsulphonyl substituent. The carboxylic esters may be prepared by reacting the alkanolamine derivative or salt thereof with an acylating agent. Examples describe the preparation of 1 - (2,3 - dimethylphenoxy) - 3 - isopropylamino-2 - propanol and many listed bases and salts, 1-(3 - ethoxyphenoxy) - 3 - isopropylamino - 2-propanol oxalate, 1 - isopropylamino - 3 - (3-tolyloxy) - 2 - propanol, 1 - (4 - benzyloxyphenoxy) - 3 - isopropylamino - 2 - propanol, 1-isopropyl - amino - 3 - pentafluorophenoxy - 2-propanol and many other compounds. Suitable esters mentioned are derived from saturated or unsaturated aliphatic carboxylic acids (not more than 20 C) e.g. acetic, palmitic, stearic or oleic acids, or aromatic e.g. benzoic acid and salts may be hydrochlorides, hydrobromides, phosphates or sulphates or oxalates, lactates, tartrates, acetates, salicylates, citrates, benzoates, b - naphthoates, adipates or 1,11-methylene - bis (2 - hydroxy - 3 - naphthoates) or derived from acidic synthetic resins e.g. sulphonated polystyrene resins.ALSO:Acid-addition salts of acidic synthetic resins' e.g sulphonated polystyrene with racemic alkanolamine derivatives of formula <FORM:1069345/C3/1> wherein R1, R3 and R4 represent hydrogen, R2 represents an n-propyl radical and the benzene radical (A) stands for the 3-tolyl, 2,5-dichlorophenyl or 3-methoxy phenyl radical; or wherein R1 represents hydrogen or an alkyl radical (not more than 5 C), R2 a branched chain alkyl or hydroxyalkyl (not more than 10 C), or for an alkyl (not more than 10 C) substituted by alkoxy (not more than 5 C), or for a cycloalkyl or alkenyl radical (not more than 5 C) or for branched chain aralkyl radical (not more than 15 C) which may optionally be substituted by one or more halogen atoms, hydroxy radicals or alkoxy radicals (not more than 5 C), R3 and R4 which may be the same or different, represent hydrogen or for alkyl radicals (not more than 5 C) and the benzene ring (A) bears a single substituent in the 3- or 4-position only which is a halogen atom, an alkyl, alkoxy, alkylthio, alkanoyl, aralkanoyl, aroyl, aryl, aryloxy, alkylaryloxy, arylthio, arylsulphonyl, arylamino, aralkyl, aralkoxy or alkenyl radical (not more than 10 C), a halogenoalkyl radical (not more than 5 C) or a hydroxy or nitro radical, or the benzene ring (A) bears a single substituent in the 2-position only which is a hydroxy, nitro, or iodo substituent or an alkanoyl, aralkanoyl, aroyl, aryl, aryloxy, alkylaryloxy, arylthio, arylsuphonyl, arylamino, aralkyl or aralkoxy substituent (not more than 10 C), or the ring A bears two, three, four or five substituents selected from the values above for the single substituent in the 3- or 4-position (see Division C2), have b -adrenergic blocking activity. An example describes the addition of a suspension of sulphonated polystyrene resin to a solution of 1 part of 1-isopropylamino-3-(3-tolyloxy)-2-propanol hydrochloride to form a complex salt.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2871763 | 1963-07-19 | ||
GB4674063 | 1963-11-13 | ||
GB3934465A GB1123258A (en) | 1965-09-15 | 1965-09-15 | Alkanolamine derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1069345A true GB1069345A (en) | 1967-05-17 |
Family
ID=27258745
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB4716066A Expired GB1069345A (en) | 1963-07-19 | 1962-12-11 | New alkanolamine derivatives |
Country Status (5)
Country | Link |
---|---|
DK (6) | DK119063B (en) |
FR (1) | FR1394771A (en) |
GB (1) | GB1069345A (en) |
MY (1) | MY7400144A (en) |
SE (5) | SE338571B (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4080471A (en) * | 1976-06-25 | 1978-03-21 | Aktiebolaget Hassle | Use of substituted isopropylaminopropanols for inducing inotropic effects of the human heart |
US4244969A (en) * | 1974-02-14 | 1981-01-13 | Aktiebolaget Hassle | Heart active compounds |
WO1989005794A1 (en) * | 1987-12-23 | 1989-06-29 | Aktiebolaget Hässle | Novel antiarrhythmic agents i |
US5504087A (en) * | 1993-02-15 | 1996-04-02 | Senju Pharmaceutical Co., Ltd. | 1-phenoxy-2-propanol derivatives useful in treating hypertension and glaucoma |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3466325A (en) * | 1965-04-30 | 1969-09-09 | Haessle Ab | 1-(ortho-alkenyl phenoxy) - 2-hydroxy-3-isopropylaminopropanes and the salts thereof |
US4117128A (en) | 1976-08-03 | 1978-09-26 | Smithkline Corporation | Sulfonyl benzofurans and benzothiophenes having coronary vasodilator activity |
SE8401907L (en) * | 1984-04-05 | 1985-10-06 | Haessle Ab | NEW PHENOXIPROPANOLAMINE SALTS AND PHARMACEUTICAL PREPARATIONS THEREOF |
-
1962
- 1962-12-11 GB GB4716066A patent/GB1069345A/en not_active Expired
-
1963
- 1963-12-11 FR FR956847A patent/FR1394771A/en not_active Expired
-
1965
- 1965-09-09 DK DK463665A patent/DK119063B/en unknown
- 1965-09-09 DK DK463365A patent/DK117963B/en unknown
- 1965-09-09 DK DK463765A patent/DK117640B/en unknown
- 1965-09-09 DK DK463565A patent/DK117710B/en unknown
- 1965-09-09 DK DK463465A patent/DK118772B/en unknown
- 1965-12-21 SE SE16574/65A patent/SE338571B/xx unknown
- 1965-12-21 SE SE1657665A patent/SE314991B/xx unknown
- 1965-12-21 SE SE1657565A patent/SE313575B/xx unknown
- 1965-12-21 SE SE16572/65A patent/SE338569B/xx unknown
- 1965-12-21 SE SE16573/65A patent/SE338570B/xx unknown
-
1966
- 1966-07-06 DK DK349566A patent/DK113370B/en unknown
-
1974
- 1974-12-31 MY MY7400144A patent/MY7400144A/en unknown
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4244969A (en) * | 1974-02-14 | 1981-01-13 | Aktiebolaget Hassle | Heart active compounds |
US4080471A (en) * | 1976-06-25 | 1978-03-21 | Aktiebolaget Hassle | Use of substituted isopropylaminopropanols for inducing inotropic effects of the human heart |
WO1989005794A1 (en) * | 1987-12-23 | 1989-06-29 | Aktiebolaget Hässle | Novel antiarrhythmic agents i |
US5155133A (en) * | 1987-12-23 | 1992-10-13 | Aktiebolaget Hassle | Antiarrhythmic compounds and pharmaceutical compositions and methods thereof |
US5504087A (en) * | 1993-02-15 | 1996-04-02 | Senju Pharmaceutical Co., Ltd. | 1-phenoxy-2-propanol derivatives useful in treating hypertension and glaucoma |
Also Published As
Publication number | Publication date |
---|---|
DK119063B (en) | 1970-11-09 |
DK117963B (en) | 1970-06-22 |
DK117640B (en) | 1970-05-19 |
DK118772B (en) | 1970-10-05 |
SE313575B (en) | 1969-08-18 |
DK117710B (en) | 1970-05-25 |
SE338569B (en) | 1971-09-13 |
MY7400144A (en) | 1974-12-31 |
SE338571B (en) | 1971-09-13 |
DK113370B (en) | 1969-03-17 |
SE314991B (en) | 1969-09-22 |
SE338570B (en) | 1971-09-13 |
FR1394771A (en) | 1965-04-09 |
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