GB1283451A - Ortho-substituted phenol ethers, their preparation and compositions containing them - Google Patents

Ortho-substituted phenol ethers, their preparation and compositions containing them

Info

Publication number
GB1283451A
GB1283451A GB02111/70A GB1211170A GB1283451A GB 1283451 A GB1283451 A GB 1283451A GB 02111/70 A GB02111/70 A GB 02111/70A GB 1211170 A GB1211170 A GB 1211170A GB 1283451 A GB1283451 A GB 1283451A
Authority
GB
United Kingdom
Prior art keywords
general formula
group
reaction
ether
alk
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
GB02111/70A
Inventor
Peter Edward Cross
Neil Montgomery Scollick
James Robert Stichbury
Eric Frederick James Thorpe
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.)
Pfizer Ltd
Original Assignee
Pfizer 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 Pfizer Ltd filed Critical Pfizer Ltd
Priority to GB02111/70A priority Critical patent/GB1283451A/en
Priority to DE19712109941 priority patent/DE2109941A1/en
Priority to BE763744A priority patent/BE763744A/en
Priority to US00122253A priority patent/US3751470A/en
Priority to FR7108803A priority patent/FR2085705B1/fr
Priority to ES389210A priority patent/ES389210A1/en
Priority to JP46013638A priority patent/JPS5214B1/ja
Priority to ES389211A priority patent/ES389211A1/en
Publication of GB1283451A publication Critical patent/GB1283451A/en
Priority to US344426A priority patent/US3910896A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1283451 o-Vinylphenol ethers PFIZER Ltd 19 April 1971 [13 March 1970] 12111/70 Heading C2C Novel o-vinylphenol ethers of the general formula wherein R<SP>1</SP> is a saturated aliphatic or alicyclic hydrocarbon radical containing at least 5 carbon atoms, Y is either (A) a -Alk-NR<SP>2</SP>R<SP>3</SP> group, in which R<SP>2</SP> and R<SP>3</SP> are each a C 1-4 alkyl group or NR<SP>2</SP>R<SP>3</SP> is a saturated heterocyclic group and Alk is a divalent saturated aliphatic hydrocarbon group containing 2-4 carbon atoms, the free valencies being located on different carbon atoms, or (B) a group of the formula in which n is 0-3 and Z is a divalent group which completes a saturated heterocyclic ring containing at least one nitrogen atom and at least 4 carbon atoms, any such nitrogen atom being separated from the oxygen atom to which Y is attached by a chain of 2-4 carbon atoms, and R<SP>4</SP> is a hydrogen or halogen atom or a C 1-4 alkyl or alkoxy group, and their pharmaceutically-acceptable acid addition salts are prepared (a) by reaction of an alkali metal salt of an o-vinylphenol of the general formula with a halide of the general formula wherein hal is a halogen atom; (b) when Y is a -Alk-NR<SP>2</SP>R<SP>3</SP> group, by reaction of an o-vinylphenol haloalkyl ether of the general formula with an amine of the general formula HNR<SP>2</SP>R<SP>3</SP>; (c) by dehydration of an o-(1-hydroxy-ethyl)- phenol ether of the general formula or dehydrohalogenation of the corresponding o-(1-haloethyl)-phenol ether; and (d) when R<SP>4</SP> is a hydrogen atom or an alkyl or alkoxy group, by dehydration of an o-(2-hydroxyethyl)-phenol ether of the general formula or dehydrohalogenation of the corresponding o-(2-haloethyl)-phenol ether; followed optionally by salification of the product. o-(1-Hydroxyethyl)-phenol ethers of the seventh general formula above are prepared (a) by reaction of a salicylaldehyde of the general formula with magnesium or lithium and a halide of the general formula hal-CH 2 -R<SP>1</SP> or (b) by reduction of an o-acylphenol ether of the general formula (which is prepared, when Y is (A), by reaction of a 4-R<SP>4</SP>-phenol and a carboxylic acid of the general formula R<SP>1</SP>CH 2 COOH in the presence of a Lewis acid and (i) reaction of the resulting o-acylphenol of the general formula with a halide of the general formula hal-Alk-Q, wherein Q is an arylsulphonyloxy group, and reaction of the resulting o-acylphenol hal-Alk ether with an amine of the fifth general formula above or (ii) reaction of said o-acylphenol with an alkali metal compound and a halide of the third general formula above). Pharmaceutical compositions having antihistamine activity comprise, as active ingredient, an o-vinyl-phenol ether of the first general formula above or a pharmaceutically acceptable acid addition salt thereof, together with a pharmaceutical carrier or diluent, and may be administered orally or parenterally.
GB02111/70A 1970-03-13 1970-03-13 Ortho-substituted phenol ethers, their preparation and compositions containing them Expired GB1283451A (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
GB02111/70A GB1283451A (en) 1970-03-13 1970-03-13 Ortho-substituted phenol ethers, their preparation and compositions containing them
DE19712109941 DE2109941A1 (en) 1970-03-13 1971-03-02 Ortho-substituted phenoxy amines
BE763744A BE763744A (en) 1970-03-13 1971-03-03 NEW ANTIHISTAMINE DERIVATIVES OF THE CLASS OF PHENOXY-AMINES SUBSTITUTED IN ORTHO
US00122253A US3751470A (en) 1970-03-13 1971-03-08 N,n-dialkyl-2-(2-(2-cycloalkylvinyl)phenoxy)alkylamines
FR7108803A FR2085705B1 (en) 1970-03-13 1971-03-12
ES389210A ES389210A1 (en) 1970-03-13 1971-03-13 N,n-dialkyl-2-(2-(2-cycloalkylvinyl)phenoxy)alkylamines
JP46013638A JPS5214B1 (en) 1970-03-13 1971-03-13
ES389211A ES389211A1 (en) 1970-03-13 1971-03-13 N,n-dialkyl-2-(2-(2-cycloalkylvinyl)phenoxy)alkylamines
US344426A US3910896A (en) 1970-03-13 1973-03-23 Substituted phenoxyalkylamines as gastric anti-secretory agents

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB02111/70A GB1283451A (en) 1970-03-13 1970-03-13 Ortho-substituted phenol ethers, their preparation and compositions containing them

Publications (1)

Publication Number Publication Date
GB1283451A true GB1283451A (en) 1972-07-26

Family

ID=9998576

Family Applications (1)

Application Number Title Priority Date Filing Date
GB02111/70A Expired GB1283451A (en) 1970-03-13 1970-03-13 Ortho-substituted phenol ethers, their preparation and compositions containing them

Country Status (7)

Country Link
US (1) US3751470A (en)
JP (1) JPS5214B1 (en)
BE (1) BE763744A (en)
DE (1) DE2109941A1 (en)
ES (2) ES389211A1 (en)
FR (1) FR2085705B1 (en)
GB (1) GB1283451A (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3910896A (en) * 1970-03-13 1975-10-07 Pfizer Substituted phenoxyalkylamines as gastric anti-secretory agents
WO2022034121A1 (en) 2020-08-11 2022-02-17 Université De Strasbourg H2 blockers targeting liver macrophages for the prevention and treatment of liver disease and cancer

Also Published As

Publication number Publication date
FR2085705A1 (en) 1971-12-31
ES389210A1 (en) 1973-06-01
BE763744A (en) 1971-09-03
US3751470A (en) 1973-08-07
JPS5214B1 (en) 1977-01-05
DE2109941A1 (en) 1971-11-25
FR2085705B1 (en) 1974-08-30
ES389211A1 (en) 1973-06-16

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]