GB922600A - Ortho-tertiary-butyl phenolethers - Google Patents

Ortho-tertiary-butyl phenolethers

Info

Publication number
GB922600A
GB922600A GB16171/60A GB1617160A GB922600A GB 922600 A GB922600 A GB 922600A GB 16171/60 A GB16171/60 A GB 16171/60A GB 1617160 A GB1617160 A GB 1617160A GB 922600 A GB922600 A GB 922600A
Authority
GB
United Kingdom
Prior art keywords
butyl
tert
methyl
phenol
group
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
GB16171/60A
Inventor
Francis Frederick Stephens
Christopher James Sharpe
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.)
CROOKES LAB Ltd
Original Assignee
CROOKES LAB Ltd
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 CROOKES LAB Ltd filed Critical CROOKES LAB Ltd
Priority to GB16171/60A priority Critical patent/GB922600A/en
Publication of GB922600A publication Critical patent/GB922600A/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
    • C07D211/08—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
    • C07D211/10—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 radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
    • C07D211/14—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 radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
    • 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
    • C07D211/56—Nitrogen atoms
    • C07D211/58—Nitrogen atoms attached in position 4

Abstract

The invention comprises ortho tert. butyl ethylamines of the general formula <FORM:0922600/IV(a)/1> where R1 and R2, which may be the same or different, represent a hydrogen atom or an alkyl group containing 1-4 carbon atoms or a phenethyl group, or R1 and R2 together with a nitrogen atom form a heterocyclic ring, R3 represents a hydrogen atom or an alkyl group containing 1-4 carbon atoms, R4 and R5 may be a hydrogen or an alkyl group containing 1-4 carbon atoms or an alkoxy, hydroxy, amino or acylamino group, together with the acid addition salts and quaternary compounds derived by quaternisation with a compound R6X where R6 represents an alkyl group and X represents the anion associated with the quaternary compound. The compounds may be prepared by (1) reacting the substituted o-tert. butyl phenol with a b -dialkylamino alkyl halide, (2) by converting the phenol to the phenol ether containing a reactive group in the b -position, such as halo or p-toluene sulphonyloxy group, which is subsequently reacted with an alkyl or dialkyl-amine or (3) by converting the phenol to the a -cyanoalkyl ether which is subsequently reduced and the primary amino group converted to a secondary or tertiary amino group if desired. Examples describe the preparation of 2-(b -diethylaminoethoxy)-4-methyl-, 2-(b -aminoethoxy)-4-methyl-, 2-(b -phenethylaminoethoxy)- 4-methyl-, 4-acetamido-2-(b -diethylaminoethoxy)- and 2-(b -diethylaminoethoxy)- 4-hydroxytert. butyl benzene and 2-(2-t. butyl-5-methylphenoxy)-ethyl-triethylammonium iodide, 2-(b - phenethylamino-ethoxy)-4-methyl-tert. butyl benzene isethionate, 2-(2-t. butyl-5-hydroxy-4-methylphenoxy)- ethyl triethylammonium iodide, 2-(2-t. butyl-4-methoxy phenoxy) ethyl trimethylammonium isethionate and 2-(b -N-piperidino-ethoxy)-tert. butyl benzene citrate. A further list of compounds falling within the general formula is also given. The above compounds and their acid addition salts have central nervous depressant and analgesic properties while the quaternary salts have long-acting local anaesthetic and sympathetic nervous system blocking properties. The pharmacological properties are compared with those of pethidine and chloropromazine.
GB16171/60A 1960-05-06 1960-05-06 Ortho-tertiary-butyl phenolethers Expired GB922600A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB16171/60A GB922600A (en) 1960-05-06 1960-05-06 Ortho-tertiary-butyl phenolethers

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB16171/60A GB922600A (en) 1960-05-06 1960-05-06 Ortho-tertiary-butyl phenolethers

Publications (1)

Publication Number Publication Date
GB922600A true GB922600A (en) 1963-04-03

Family

ID=10072459

Family Applications (1)

Application Number Title Priority Date Filing Date
GB16171/60A Expired GB922600A (en) 1960-05-06 1960-05-06 Ortho-tertiary-butyl phenolethers

Country Status (1)

Country Link
GB (1) GB922600A (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3408387A (en) * 1964-09-30 1968-10-29 Ici Ltd Amidoaroxyalkanolamines
EP0062596A1 (en) * 1981-04-06 1982-10-13 Cortial S.A. Derivatives of 4-aminoethoxy-5-isopropyl-2-methyl phenol, process for their preparation and their use as medicines
EP0269363A2 (en) * 1986-11-21 1988-06-01 A/S Cheminova Amino-alkylated hydroxy compounds and their use as fungicides
WO2003011210A2 (en) * 2001-07-31 2003-02-13 Astrazeneca Ab Arylheteroalkylamine derivatives and their use as inhibitors of nitric oxide synthase
US6887871B2 (en) 2000-02-23 2005-05-03 Astrazeneca Ab Use of phenylheteroakylamine derivatives
US6900243B2 (en) 2000-02-23 2005-05-31 Astrazeneca Ab Phenylheteroalkylamine derivatives
US6953797B2 (en) 2000-02-23 2005-10-11 Astrazeneca Ab Use of phenylheteroalkylamine derivatives

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3408387A (en) * 1964-09-30 1968-10-29 Ici Ltd Amidoaroxyalkanolamines
EP0062596A1 (en) * 1981-04-06 1982-10-13 Cortial S.A. Derivatives of 4-aminoethoxy-5-isopropyl-2-methyl phenol, process for their preparation and their use as medicines
EP0269363A2 (en) * 1986-11-21 1988-06-01 A/S Cheminova Amino-alkylated hydroxy compounds and their use as fungicides
WO1988003756A1 (en) * 1986-11-21 1988-06-02 A/S Cheminova Amino-alkylated hydroxy compounds and their use as fungicides
EP0269363A3 (en) * 1986-11-21 1989-11-23 A/S Cheminova Amino-alkylated hydroxy compounds and their use as fungicides
US6887871B2 (en) 2000-02-23 2005-05-03 Astrazeneca Ab Use of phenylheteroakylamine derivatives
US6900243B2 (en) 2000-02-23 2005-05-31 Astrazeneca Ab Phenylheteroalkylamine derivatives
US6953797B2 (en) 2000-02-23 2005-10-11 Astrazeneca Ab Use of phenylheteroalkylamine derivatives
WO2003011210A2 (en) * 2001-07-31 2003-02-13 Astrazeneca Ab Arylheteroalkylamine derivatives and their use as inhibitors of nitric oxide synthase
US7223794B2 (en) 2001-07-31 2007-05-29 Astrazeneca Ab Arylheteroalkylamine derivatives and their use as inhibitors of nitric oxide synthase
WO2003011210A3 (en) * 2001-07-31 2007-10-25 Astrazeneca Ab Arylheteroalkylamine derivatives and their use as inhibitors of nitric oxide synthase

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