GB1364280A - 1-phenoxy-2-hydroxy-3-hydroxyalkylamino-propanes an processes for their preparation - Google Patents

1-phenoxy-2-hydroxy-3-hydroxyalkylamino-propanes an processes for their preparation

Info

Publication number
GB1364280A
GB1364280A GB4610371A GB4610371A GB1364280A GB 1364280 A GB1364280 A GB 1364280A GB 4610371 A GB4610371 A GB 4610371A GB 4610371 A GB4610371 A GB 4610371A GB 1364280 A GB1364280 A GB 1364280A
Authority
GB
United Kingdom
Prior art keywords
compound
formula
hydrogen
group
hydrolysing
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
Application number
GB4610371A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
CH Boehringer Sohn AG and Co KG
Boehringer Ingelheim GmbH
Original Assignee
CH Boehringer Sohn AG and Co KG
Boehringer Ingelheim GmbH
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by CH Boehringer Sohn AG and Co KG, Boehringer Ingelheim GmbH filed Critical CH Boehringer Sohn AG and Co KG
Publication of GB1364280A publication Critical patent/GB1364280A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/64—Oxygen atoms
    • 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

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (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)

Abstract

1364280 1-phenoxy, 2-hydroxy, 3-hydroxyalkylamino-propanes BOEHRINGER INGELHEIM GmbH 4 Oct 1971 [5 Oct 1970] 46103/71 Heading C2C [Also in Division A5] Novel compounds of general Formula I and their esters and acid addition salts, where R 1 represents cyano, ethynyl, propargyl, allyl, amino, hydroxymethyl methoxy, hydroxycarbonyl methoxycarbonyl or allyloxy; R 2 represents a hydrogen, chlorine, methyl or cyano; or R 1 and R 2 together represent a 3,4- methylene-dioxy group; R 3 represents hydrogen and R 4 represents a straight or branched hydroxyalkyl group with 3 to 6 C atoms (with the proviso that R 4 is not 1,1-dimethyl-2- hydroxyethyl or 1,2 - dimethyl - 2 - hydroxyethyl when R 1 is 4-amino) are prepared by (1) reacting a compound of Formula II where Z represents the group or -CH.OH-CH 2 -Halogen with an amine NH 2 -R 4 , (2) hydrolysing or hydrogenolysing a compound of Formula IV where G is an acyl or tetrahydropyranyl group, (3) reacting a compound of Formula V with a hydroxyalkyl (with 3 to 6 C atoms)- halide, -tosylate or -mesylate or with a hydroxyaldehyde or hydroxyketone of 3 to 6 C atoms under conditions of reductive alkylation with hydrogen, (4) hydrolysing or hydrogenolysing a compound of Formula VI where Sch is preferably a benzyl carbobenzoxy or acyl group, (5) hydrolysing a compound of Formula VII preferably by using a strong alkali in an aqueous or aqueous/alcoholic medium, (6) hydrolysing or pyrolysing a compound of Formula VIII where R 5 and R 6 are either a hydrogen atom or an alkyl, aralkyl or aryl group, (7) chlorinating a compound Ar-OCH 2 -CHOH-CH 2 -NHR 4 , where Ar represents a phenyl group substituted by R<SP>1</SP> and R 3 preferably by using hydrogen peroxide and a hydrohalic acid, (8) reducing a compound II in which Z is CO-CH 2 -NHR 4 or CHOH-CO-NHR 4 , (9) reacting by known methods a compound X in which A is halogen, aldehyde, amide, oxime, haloalkyl nitro or alkoxy carbonyl to form a compound I in which R 1 is cyano, amino hydroxymethyl, or hydroxycarbonyl, or (10) reacting by known methods a compound X1 in which B is aldehyde or amino to form a compound I in which R 2 is other than hydrogen. Compounds I may be formed as their optical isomers. Acetates and propionates of compounds I may be formed by conventional procedures. Compounds I show #-adrenolytic activity and blood-pressure decreasing properties and form with a carrier or excipient a pharmaceutical composition which may be administered orally rectally or parenterally. The compositions may include coronary dilators, sympathicominetics cardiac glycosides or tranquillizers and in particular 2,6-bis-(diethanolamino-)-4,8-dipiperidino-pyrimido [5,4-d]-pyrimidine.
GB4610371A 1970-10-05 1971-10-04 1-phenoxy-2-hydroxy-3-hydroxyalkylamino-propanes an processes for their preparation Expired GB1364280A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19702048838 DE2048838A1 (en) 1970-10-05 1970-10-05 New 1 phenoxy 2 hydroxy 3 hydroxyal kylaminopropane and process for their manufacture

Publications (1)

Publication Number Publication Date
GB1364280A true GB1364280A (en) 1974-08-21

Family

ID=5784228

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4610371A Expired GB1364280A (en) 1970-10-05 1971-10-04 1-phenoxy-2-hydroxy-3-hydroxyalkylamino-propanes an processes for their preparation

Country Status (26)

Country Link
JP (1) JPS5710097B1 (en)
AT (10) AT318564B (en)
AU (1) AU469119B2 (en)
BE (1) BE773472A (en)
BG (8) BG20100A3 (en)
CA (1) CA1008866A (en)
CH (11) CH583685A5 (en)
CS (2) CS172932B2 (en)
DE (1) DE2048838A1 (en)
DK (1) DK130958B (en)
ES (8) ES395671A1 (en)
FI (1) FI55491C (en)
FR (1) FR2110230B1 (en)
GB (1) GB1364280A (en)
HU (1) HU163226B (en)
IE (1) IE35693B1 (en)
IL (1) IL37830A (en)
NL (1) NL174249C (en)
NO (1) NO132835C (en)
PH (1) PH9959A (en)
PL (10) PL84225B1 (en)
RO (8) RO62357A (en)
SE (1) SE383631B (en)
SU (2) SU419024A3 (en)
YU (2) YU35576B (en)
ZA (1) ZA716643B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3248835A1 (en) * 1981-06-23 1983-06-30 American Hospital Supply Corp COMPOSITIONS FOR TREATING GLAUCOMA

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4055658A (en) * 1976-05-17 1977-10-25 Mead Johnson & Company Cyanomethylphenethanolamines
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
US4652584A (en) * 1984-07-13 1987-03-24 Mcneilab, Inc. Acetylenic phenoxypropanol derivatives and pharmaceutical compositions for the treatment of hypertension
DE4422707A1 (en) * 1994-06-29 1996-01-04 Hoechst Ag Process for dyeing aminated cellulose / polyester blends with fiber-reactive disperse dyes
JP4934287B2 (en) * 2005-04-05 2012-05-16 花王株式会社 Whitening agent

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DD45360A (en) *
CA945172A (en) * 1969-02-21 1974-04-09 Imperial Chemical Industries Limited Alkanolamine derivatives

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3248835A1 (en) * 1981-06-23 1983-06-30 American Hospital Supply Corp COMPOSITIONS FOR TREATING GLAUCOMA

Also Published As

Publication number Publication date
ES399868A1 (en) 1975-06-16
DK130958B (en) 1975-05-12
SU419024A3 (en) 1974-03-05
AT318569B (en) 1974-10-25
FI55491C (en) 1979-08-10
AT318567B (en) 1974-10-25
JPS5710097B1 (en) 1982-02-24
CH564515A5 (en) 1975-07-31
ES399870A1 (en) 1975-07-16
IE35693L (en) 1972-04-05
ES399872A1 (en) 1975-07-01
RO62313A (en) 1977-08-15
AT318566B (en) 1974-10-25
NO132835C (en) 1976-01-14
FR2110230A1 (en) 1972-06-02
FR2110230B1 (en) 1975-03-14
CH564516A5 (en) 1975-07-31
RO62355A (en) 1977-10-15
BG18857A3 (en) 1975-03-20
ES399869A1 (en) 1975-06-16
PH9959A (en) 1976-06-14
PL84224B1 (en) 1976-03-31
PL84212B1 (en) 1976-03-31
BG18858A3 (en) 1975-03-20
CH563342A5 (en) 1975-06-30
IE35693B1 (en) 1976-04-28
BG19134A3 (en) 1975-04-30
RO62267A (en) 1978-01-15
RO62359A (en) 1977-11-15
AU3418271A (en) 1973-04-12
CH587227A5 (en) 1977-04-29
NL174249C (en) 1984-05-16
SU677649A3 (en) 1979-07-30
BG19133A3 (en) 1975-04-30
PL82037B1 (en) 1975-10-31
RO61540A (en) 1977-02-15
DK130958C (en) 1975-10-13
AT318571B (en) 1974-10-25
PL84276B1 (en) 1976-03-31
BE773472A (en) 1972-04-04
ES395671A1 (en) 1974-10-16
PL84225B1 (en) 1976-03-31
PL84267B1 (en) 1976-03-31
ES399873A1 (en) 1975-07-01
BG20100A3 (en) 1975-10-30
FI55491B (en) 1979-04-30
IL37830A (en) 1975-03-13
CH584185A5 (en) 1977-01-31
HU163226B (en) 1973-07-28
AT318572B (en) 1974-10-25
BG20338A3 (en) 1975-11-05
SE383631B (en) 1976-03-22
RO62357A (en) 1977-10-15
AT318565B (en) 1974-10-25
CH564507A5 (en) 1975-07-31
DE2048838A1 (en) 1972-04-06
YU23679A (en) 1980-10-31
IL37830A0 (en) 1971-12-29
YU35577B (en) 1981-04-30
YU250571A (en) 1980-10-31
BG18859A3 (en) 1975-03-20
CH583685A5 (en) 1977-01-14
AT318561B (en) 1974-10-25
PL84227B1 (en) 1976-03-31
AT318568B (en) 1974-10-25
CA1008866A (en) 1977-04-19
YU35576B (en) 1981-04-30
ES399871A1 (en) 1975-06-16
CH583686A5 (en) 1977-01-14
RO62358A (en) 1978-04-15
CH563341A5 (en) 1975-06-30
NL174249B (en) 1983-12-16
PL84226B1 (en) 1976-03-31
CS172950B2 (en) 1977-01-28
PL84223B1 (en) 1976-03-31
AU469119B2 (en) 1976-02-05
CS172932B2 (en) 1977-01-28
AT318570B (en) 1974-10-25
CH583687A5 (en) 1977-01-14
NL7113581A (en) 1972-04-07
NO132835B (en) 1975-10-06
ES399874A1 (en) 1975-07-01
RO62356A (en) 1977-08-15
PL84396B1 (en) 1976-03-31
AT318564B (en) 1974-10-25
BG19793A3 (en) 1975-10-10
CH587223A5 (en) 1977-04-29
ZA716643B (en) 1973-06-27

Similar Documents

Publication Publication Date Title
US4017608A (en) Therapeutic composition and method of therapeutically treating warm blooded animals therewith
GB1513950A (en) Benzomorphane derivatives
SE409030B (en) PROCEDURE FOR THE PREPARATION OF CERTAIN STATED N-SUBSTITUTED BETA-AMINO-ALFA-BENZYLACRYLNITRILE DERIVATIVES
GB1364280A (en) 1-phenoxy-2-hydroxy-3-hydroxyalkylamino-propanes an processes for their preparation
US4868303A (en) Bis-dioxopiperazine derivatives
US3268582A (en) Phenylalkyl-carboxylic acid amides
US3939146A (en) Novel ethereal monosubstitutions of monosaccharide derivatives
IL39147A (en) Amino alcohols derived from ortho trans-hydroxycinnamic acids,their esters and their amides,preparation thereof and pharmaceutical compositions containing them
GB1384115A (en) Furylmethyl-benzomorphane derivatives and pharmaceutical composi tions containing them
USRE30379E (en) Ethereal monosubstitutions of monosaccharide derivatives
GB1111338A (en) Aralkyl substituted resorcinols
EP0049565A3 (en) Derivatives of substituted n-alkylimidazoles, their preparation and pharmaceutical compositions containing them
GB1031425A (en) New aralkylamines and their preparation
Raiziss et al. 2-Sulfanilyl-aminothiazoline
SE7415015L (en) METHODS OF PRODUCING NEW 2-PHENYLHYDRAZINO-THIAZOLINES OR -TIAZINES
ES2029830T3 (en) A PROCEDURE FOR PREPARING A DERIVATIVE OF 6-CETOPROSTAGLANDINA E1.
GB1295206A (en)
ATE22011T1 (en) VIRUS VACCINES AND PROCESSES FOR THEIR MANUFACTURE.
DK455285A (en) 2-pyridin-thiol derivatives
US3415866A (en) alpha-alkylidene-3,4-disubstituted-phenylacetonitriles
ES8502700A1 (en) Derivatives of tetrahydrobenzothiazole and herbicidal compositions containing the same as an active ingredient
US3472871A (en) 1 - methyl - 3 - hydroxy - 6 - oxo - 5 - ((amido) alkanoyl - hydrozo) -2,3,5,6-tetrahydroindoles
GB1430868A (en) Coumarin derivatives
US5393889A (en) Water soluble bis-dioxopiperazine derivatives
US2494125A (en) S-acylamino ukacils and process of

Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
429A Application made for amendment of specification (sect. 29/1949)
429H Application (made) for amendment of specification now open to opposition (sect. 29/1949)
429D Case decided by the comptroller ** specification amended (sect. 29/1949)
SPA Amended specification published
PCNP Patent ceased through non-payment of renewal fee