GB893088A - Improvements in or relating to substituted amines - Google Patents

Improvements in or relating to substituted amines

Info

Publication number
GB893088A
GB893088A GB1177658A GB1177658A GB893088A GB 893088 A GB893088 A GB 893088A GB 1177658 A GB1177658 A GB 1177658A GB 1177658 A GB1177658 A GB 1177658A GB 893088 A GB893088 A GB 893088A
Authority
GB
United Kingdom
Prior art keywords
formula
compound
group
alcohol
hydrogen
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
GB1177658A
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.)
Koninklijke Philips NV
Original Assignee
Philips Gloeilampenfabrieken NV
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 Philips Gloeilampenfabrieken NV filed Critical Philips Gloeilampenfabrieken NV
Publication of GB893088A publication Critical patent/GB893088A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
    • C07D211/40—Oxygen atoms
    • C07D211/42—Oxygen atoms attached in position 3 or 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
    • C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/30—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
    • C07D211/32—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
    • C07D211/38—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
    • C07D211/40—Oxygen atoms
    • C07D211/44—Oxygen atoms attached in position 4
    • C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

<FORM:0893088/IV (b)/1> <FORM:0893088/IV (b)/2> <FORM:0893088/IV (b)/3> <FORM:0893088/IV (b)/4> <FORM:0893088/IV (b)/5> <FORM:0893088/IV (b)/6> <FORM:0893088/IV (b)/7> <FORM:0893088/IV (b)/8> <FORM:0893088/IV (b)/9> <FORM:0893088/IV (b)/100> <FORM:0893088/IV <FORM:0893088/IV (b)/123> <FORM:0893088/IV (b)/134> <FORM:0893088/IV (b)/145> <FORM:0893088/IV (b)/156> <FORM:0893088/IV (b)/167> <FORM:0893088/IV (b)/178> <FORM:0893088/IV (b)/189> wherein R1, R2 and R3 which are the same or different designate hydrogen, a hydroxy group ethanol or other aliphatic alcohol containing 1 to 6 carbon atoms, R4 is hydrogen or a hydroxy group, R5 is hydrogen or an alkyl group, R6 is hydrogen or an alkyl, or aralkyl group and Y is an alkyl-cycloalkylene or alkylene group or R6, Y1 and the nitrogen atom together form a piperidine ring with or without an alkyl group or a hydroxy group etherified with methanol, as substituent therein, or an acid-addition salt thereof and processes for the preparation thereof (a) by reacting a compound of the formula I with one of the compounds of the formula II, i.e. by esterification; (b) by coupling a compound of formula XII with a compound of formula XIII wherein Me is an alkali metal atom; (c) reacting a compound of the formula XV with a compound of the formula XVI wherein X is a chlorine bromine or iodine atom or a keto- or aldehyde-oxygen atom, in the presence of an acid binder when X is halogen; when X is a keto or aldehyde oxygen atom reduction may be effected with hydrogen and a metal catalyst; (d) introducing the group R5 into compounds of the formula XIX by reaction with a dialkyl sulphate or with a compound of the formula R5 Hlg wherein Hlg is bromine or chlorine (e) hydrogenating compounds of the formula XX, e.g. in the presence of platinum or palladium. The amino-alcohols of the formula I may be obtained by reacting a substituted aralkyl compound of the formula III with an amino alcohol of the formula IV or, alternatively, by reacting a substituted aralkylamine of the formula V with a half-ester-half-acid halide of the formula VI in which Y1 is a branched or unbranched alkylene radical to produce compounds of the formula VII which may be reduced with LiAlH4 to obtain the desired amino alcohol I. Further methods of making compound I comprise (a) reacting a compound of the formula V with a halogen alcohol of the formula VIII, or a halogen aldehyde or halogen ketone, or ethylene oxide, (b) catalytically reducing a keto or aldehyde-alcohol with amines of the formula V, (c) catalytically hydrogenating the aralkyl ketones or aldehydes of the formula IX in the presence of amino-alcohols of the formula X, (d) converting tetrahydrofurfurylamines of the formula IX with HBr and adding alkali to effect cyclization- Compounds of the formula XII may be obtained by reacting the corresponding alcohols with PCl5, SO2Cl2, POCl3, PBr3 or SO2Br2 or by reacting compounds of the formula V with a compound of the formula XIV. Compounds of the formula XVI may be obtained (a) by esterifying a compound of the formula II with a divalent alcohol of the formula XVII followed by treatment with a halogenating agent (b) by esterifying a compound of the formula II with a halogen alcohol of the formula VIII, (c) esterifying a compound of the formula XIII with an aliphatic dihalogen compound of the formula XIV, by the esterification of an acid or acid halide of formula II with an aldehyde or keto-alcohol. Alternatively, the esterification may be effected with a di-alcohol after which the non-esterified alcohol group is oxidised to an aldehyde or keto group. In another method the keto or aldehyde esters are obtained by esterifying a compound of the formula XIII with a halogen ketone or halogen aldehyde. The products of the invention may be produced in the form of their salts, e.g. hydrochlorides, hydrobromides, acetates, oxalates, citrates, sulphates and phosphates. Detailed examples are given.ALSO:Pharmaceutical preparations for reducing the blood pressure comprise a compound having the formula <FORM:0893088/VI/1> or an acid addition salt thereof, in which formula R1, R2 and R3, which are the same or different designate hydrogen, a hydroxy group, or a hydroxy group etherified with methanol, ethanol or other aliphatic alcohol containing 1-6 carbon atoms, R4 designates hydrogen or a hydroxy group, R5 designates hydrogen or an alkyl group, R6 designates hydrogen or an alkyl or aralkyl group and Y designates an alkylcycloalkylene or alkylene group or R6, Y and the nitrogen atom together form a piperidine ring with or without an alkyl group as substituent therein, R7, R8 and R9 designate a hydroxy group or a hydroxy group etherified with methanol, ethanol or other aliphatic alcohol containing 1-6 carbon atoms mixed with an inert pharmaceutical carrier. They may be administered orally in the form of a tablet when mixed with conventional fillers or parenterally in the form of a solution of the non-toxic addition salts.
GB1177658A 1957-04-13 1958-04-14 Improvements in or relating to substituted amines Expired GB893088A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
NL216318 1957-04-13

Publications (1)

Publication Number Publication Date
GB893088A true GB893088A (en) 1962-04-04

Family

ID=19750870

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1177658A Expired GB893088A (en) 1957-04-13 1958-04-14 Improvements in or relating to substituted amines

Country Status (4)

Country Link
CH (4) CH377796A (en)
DK (1) DK104415C (en)
GB (1) GB893088A (en)
NL (2) NL112514C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994008945A1 (en) * 1992-10-16 1994-04-28 Byk Nederland Bv Substituted ethanolamine esters

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HU165022B (en) * 1972-04-28 1974-06-28
EP0142283B1 (en) * 1983-10-25 1991-01-30 FISONS plc Phenylethylamines, process for their preparation and compositions containing them

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994008945A1 (en) * 1992-10-16 1994-04-28 Byk Nederland Bv Substituted ethanolamine esters
US5599966A (en) * 1992-10-16 1997-02-04 Byk Nederland Bv Substituted ethanolamine esters

Also Published As

Publication number Publication date
CH405356A (en) 1966-01-15
DK104415C (en) 1966-05-16
CH377797A (en) 1964-05-31
CH377794A (en) 1964-05-31
NL216318A (en)
NL112514C (en)
CH377796A (en) 1964-05-31

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