GB1088114A - Aminoethyl ethers of cyclohexanols - Google Patents

Aminoethyl ethers of cyclohexanols

Info

Publication number
GB1088114A
GB1088114A GB1096565A GB1096565A GB1088114A GB 1088114 A GB1088114 A GB 1088114A GB 1096565 A GB1096565 A GB 1096565A GB 1096565 A GB1096565 A GB 1096565A GB 1088114 A GB1088114 A GB 1088114A
Authority
GB
United Kingdom
Prior art keywords
formula
compound
alkyl
reaction
acid addition
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
GB1096565A
Inventor
Wijbe Thomas Nauta
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 Pharmaceutische Fabrieken NV
Original Assignee
Koninklijke Pharmaceutische Fabrieken 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 Koninklijke Pharmaceutische Fabrieken NV filed Critical Koninklijke Pharmaceutische Fabrieken NV
Priority to GB1092665A priority Critical patent/GB1088113A/en
Priority to GB1096565A priority patent/GB1088114A/en
Priority to IL25356A priority patent/IL25356A/en
Priority to NO162077A priority patent/NO118745B/no
Priority to AT239966A priority patent/AT262269B/en
Priority to CH360766A priority patent/CH475929A/en
Priority to SE03352/66A priority patent/SE329844B/xx
Priority to CH360866A priority patent/CH484052A/en
Priority to DE19661593147 priority patent/DE1593147A1/en
Priority to DE19661593146 priority patent/DE1593146A1/en
Priority to NL6603371A priority patent/NL6603371A/xx
Priority to BE677868D priority patent/BE677868A/xx
Priority to FR1568727D priority patent/FR1568727A/fr
Priority to NL6603370A priority patent/NL6603370A/xx
Priority to BE677867D priority patent/BE677867A/xx
Priority to FR1568726D priority patent/FR1568726A/fr
Priority to FR64946A priority patent/FR7372M/fr
Priority to FR64945A priority patent/FR6843M/fr
Publication of GB1088114A publication Critical patent/GB1088114A/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

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)

Abstract

Novel compounds of the formula <FORM:1088114/C2/1> wherein R1, R2 and R4 are C1- 6\t alkyl, and R3 and R5 are H or C1- 6 alkyl, or else the group <FORM:1088114/C2/2> represents a saturated, unsubstituted 5 or 6-membered ring which may contain a further hetero-atom other than the N already present, and the acid addition salts thereof, may be prepared by one of three methods: (a) by reaction of a cyclohexanol derivative of formula <FORM:1088114/C2/3> with the required aminoethyl halide or acid addition salt thereof; (b) by reaction of a cyclohexanol derivative of the second formula given above with a 1,2-dihaloethane, and the resulting compound of formula <FORM:1088114/C2/4> is reacted with an amine <FORM:1088114/C2/5> (c) by the reduction of the keto group to methylone in a compound of formula <FORM:1088114/C2/6> In all these formulae, R1-R5 are as defined above. Pharmaceutical compositions comprise as active ingredient at least one compound of the first formula given above, together with a pharmaceutically acceptable carrier. The compositions may take the form of pills, tablets, capsules, emulsions, syrups, solutions or elixirs, suitable for oral or parenteral administration. They have activity in dilating coronary bloodvessels, coupled with a positive isotropic action, and increase the refractory period. In addition they may have sedative, hypnotic and/or muscle relaxing activity.
GB1096565A 1954-04-14 1965-03-15 Aminoethyl ethers of cyclohexanols Expired GB1088114A (en)

Priority Applications (18)

Application Number Priority Date Filing Date Title
GB1092665A GB1088113A (en) 1965-03-15 1965-03-15 Cyclohexanol derivatives
GB1096565A GB1088114A (en) 1965-03-15 1965-03-15 Aminoethyl ethers of cyclohexanols
IL25356A IL25356A (en) 1965-03-15 1966-03-10 Aminoethyl ethers of cyclohexanol derivatives,their preparation and use
NO162077A NO118745B (en) 1965-03-15 1966-03-12
AT239966A AT262269B (en) 1965-03-15 1966-03-14 Process for the preparation of new 1-phenly-2-alkylcyclohexyl-aminoethyl-ethers and their acid addition salts
CH360766A CH475929A (en) 1965-03-15 1966-03-14 Process for the preparation of new cyclohexanol derivatives
SE03352/66A SE329844B (en) 1965-03-15 1966-03-14
CH360866A CH484052A (en) 1965-03-15 1966-03-14 Process for the preparation of new aminoethyl ethers of cyclohexanol
DE19661593147 DE1593147A1 (en) 1965-03-15 1966-03-14 Cyclohexanols, processes for their preparation and pharmaceuticals containing these compounds
DE19661593146 DE1593146A1 (en) 1965-03-15 1966-03-14 Cyclohexanolaminoethyl ether and process for their preparation
NL6603371A NL6603371A (en) 1965-03-15 1966-03-15
BE677868D BE677868A (en) 1965-03-15 1966-03-15
FR1568727D FR1568727A (en) 1965-03-15 1966-03-15
NL6603370A NL6603370A (en) 1965-03-15 1966-03-15
BE677867D BE677867A (en) 1965-03-15 1966-03-15
FR1568726D FR1568726A (en) 1965-03-15 1966-03-15
FR64946A FR7372M (en) 1954-04-14 1966-06-10
FR64945A FR6843M (en) 1965-03-15 1966-06-10

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB1092665A GB1088113A (en) 1965-03-15 1965-03-15 Cyclohexanol derivatives
GB1096565A GB1088114A (en) 1965-03-15 1965-03-15 Aminoethyl ethers of cyclohexanols

Publications (1)

Publication Number Publication Date
GB1088114A true GB1088114A (en) 1967-10-25

Family

ID=26247857

Family Applications (2)

Application Number Title Priority Date Filing Date
GB1092665A Expired GB1088113A (en) 1954-04-14 1965-03-15 Cyclohexanol derivatives
GB1096565A Expired GB1088114A (en) 1954-04-14 1965-03-15 Aminoethyl ethers of cyclohexanols

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB1092665A Expired GB1088113A (en) 1954-04-14 1965-03-15 Cyclohexanol derivatives

Country Status (6)

Country Link
BE (2) BE677867A (en)
CH (2) CH484052A (en)
DE (2) DE1593147A1 (en)
FR (4) FR1568726A (en)
GB (2) GB1088113A (en)
NL (2) NL6603371A (en)

Also Published As

Publication number Publication date
CH475929A (en) 1969-07-31
FR1568726A (en) 1969-05-30
FR6843M (en) 1969-04-08
NL6603370A (en) 1966-09-16
DE1593146A1 (en) 1970-07-16
DE1593147A1 (en) 1970-05-06
BE677867A (en) 1966-09-15
NL6603371A (en) 1966-09-16
FR7372M (en) 1969-10-27
CH484052A (en) 1970-01-15
FR1568727A (en) 1969-05-30
BE677868A (en) 1966-09-15
GB1088113A (en) 1967-10-25

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