GB878677A - New substituted cycloalkanones and process for their manufacture - Google Patents

New substituted cycloalkanones and process for their manufacture

Info

Publication number
GB878677A
GB878677A GB39397/57A GB3939757A GB878677A GB 878677 A GB878677 A GB 878677A GB 39397/57 A GB39397/57 A GB 39397/57A GB 3939757 A GB3939757 A GB 3939757A GB 878677 A GB878677 A GB 878677A
Authority
GB
United Kingdom
Prior art keywords
cyclopentanone
radicals
group
cyclopentenyl
amino
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
GB39397/57A
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.)
BASF Schweiz AG
Original Assignee
Ciba AG
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 Ciba AG filed Critical Ciba AG
Publication of GB878677A publication Critical patent/GB878677A/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
    • C07D295/10—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 doubly bound oxygen or sulphur atoms
    • C07D295/112—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 doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • C07D295/116—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 doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings with the doubly bound oxygen or sulfur atoms directly attached to a carbocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
    • C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
    • C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom

Abstract

The invention comprises 2-(D 1-cycloalkenyl) and 2-cycloalkyl-2-aminoalkyl-cycloalkanones and their acid addition salts wherein the cyclic radicals may contain as substituents linear or cyclic aliphatic radicals, the amino group of the amino alkyl group includes alkyl-, dialkyl- or hydroxyalkyl amino groups, and radicals of cyclic amines which may contain hetero-atoms and the alkylene radical of the aminoalkyl group may have a straight or branched chain and preferably contains a chain of 2 or 3 carbon atoms and the preparation thereof by reacting a 2-cycloalkylidine-cycloalkanone with a reactive ester of an alkanol containing an amino group or a substituent replaceable by or convertible into an amino group in the presence of a condensing agent capable of promoting substitution at a methylene group, and wherein in the resulting compound a substituent replaceable by or convertible into an amino group is so replaced or converted and if desired, the double bond is hydrogenated at any desired stage of the reaction. Examples of groups replaceable by or convertible into amino groups include halogen atoms, free or etherified hydroxy groups, such as the vinyl ether, or the cyano group. 3-Methylcyclopentylidene -41- methyl-cyclopentanone is prepared from 3-methyl-cyclopentanone by condensation with itself in the presence of potassium hydroxide and 2,5-biscyclopentylidene-cyclopentanone by condensation of cyclopentanone with cyclo-pentylidene-cyclo-pentanone. 2- (D 1- cyclopentenyl)- 2- (b -chloroethyl) -2- (D 1- cyclopentenyl)- 2- (b -chloroethyl)-cyclopentanone is prepared by condensing 2-cyclopentylidene-cyclopentanone with either b -bromoethyl-vinyl ether to form 2-(D 1-cyclopentenyl)-2-(b -vinyl-oxyethyl)- cyclopentanone which is hydrolysed to the b -hydroxyethyl derivative and this reacted with thionyl chloride, or with b -bromoethyl chloride or with ethylene chlorohydrin-benzene sulphonic acid ester.ALSO:Pharmaceutical compositions for oral, enteral or parenteral administration comprise a 2-(D 1-cycloalkenyl)- or a 2-cycloalkyl-2-aminoalkyl cycloalkanone or an acid addition salt thereof in admixture or in conjunction with a suitable pharmaceutical carrier. The compounds may be substituted in the cyclic radicals by linear or cyclic aliphatic radicals, the amino group of the aminoalkyl group including alkyl-, dialkyl- and hydroxyalkylamino groups and radicals of cyclic amines which may contain further hetero atoms. The compositions may contain further therapeutically active substances. Examples are given of tablets and a solution for injection containing 2-(D 1-cyclopentenyl-2-(b -morpholinoethyl)-cyclopentanone.
GB39397/57A 1956-12-18 1957-12-18 New substituted cycloalkanones and process for their manufacture Expired GB878677A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH878677X 1956-12-18

Publications (1)

Publication Number Publication Date
GB878677A true GB878677A (en) 1961-10-04

Family

ID=4544651

Family Applications (1)

Application Number Title Priority Date Filing Date
GB39397/57A Expired GB878677A (en) 1956-12-18 1957-12-18 New substituted cycloalkanones and process for their manufacture

Country Status (2)

Country Link
GB (1) GB878677A (en)
NL (1) NL105308C (en)

Also Published As

Publication number Publication date
NL105308C (en)

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