GB912684A - New 2-basically substituted indene compounds - Google Patents

New 2-basically substituted indene compounds

Info

Publication number
GB912684A
GB912684A GB9814/59A GB981459A GB912684A GB 912684 A GB912684 A GB 912684A GB 9814/59 A GB9814/59 A GB 9814/59A GB 981459 A GB981459 A GB 981459A GB 912684 A GB912684 A GB 912684A
Authority
GB
United Kingdom
Prior art keywords
lower alkyl
acid
benzyl
tertiary amino
reacting
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
GB9814/59A
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 GB912684A publication Critical patent/GB912684A/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
    • 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
    • C07D295/06—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 halogen atoms or nitro radicals
    • C07D295/073—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 halogen atoms or nitro radicals with the ring nitrogen atoms and the substituents separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • 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
    • C07D295/096—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 separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings

Abstract

The invention comprises compounds of the general formula: <FORM:0912684/IV (b)/1> and their acid addition and quaternary ammonium salts and N-oxides wherein A represents a C1-7 alkylene group, A1 represents a C2-7 alkylene chain containing at least 2 carbon atoms in the said chain, R1 and R2 represent hydrogen or halogen atoms, or C1-7 alkyl or alkoxy groups, R3 and R4 represent alkyl or cycloalkyl groups having at most 7 carbon atoms or they form together with the amino nitrogen atom a heterocyclic ring which can be interrupted by a further nitrogen, oxygen or sulphur atom, and R5 is a hydrogen atom or a methyl group. The compounds of the invention may be prepared by reacting an appropriate 2-tertiary amino-lower alkylindane-1-one with an aryl-lower alkyl Grignard reagent or with an aryl lower alkyl metal compound, especially an alkali metal compound, and if necessary, isolating and dehydrating the 3-aryl-lower alkyl-2-tertiary amino-lower alkyl-indane-1-ols so formed, by treatment with an acid reagent. The compounds may also be prepared by cyclizing a 3-aryl-5-tertiary amino-lower alkyl-1-phenylpentane-2-one with polyphosphoric acid. The N-oxides are prepared by reacting the bases with hydrogen peroxide and the quaternary ammonium salts by reacting the base with an ester formed from a hydroxylated hydrocarbon compound and a strong inorganic or organic base. The 2-tertiary amino-lower alkyl-indane-1-ones used as starting materials are prepared by esterifying an appropriate a -benzyl-malonic acid to form a lower alkyl or a tetrahydropyranyl ester, reacting this with a reactive ester of a tertiary amino alkanol and an acid to form the corresponding a -benzyl-tertiary amino-lower alkyl-malonic acid ester, hydrolysing this to the di-acid, decarboxylating the diacid to the mono-acid and cyclizing the lastnamed in the presence of polyphosphoric acid. The malonic ester may also be cyclized direct. 3-Benzyl-5-dimethylamino-1-phenyl-pentane-2-one is prepared by reacting diethyl a -benzyl-a -(21-dimethylaminoethyl)-malonate with potassium hydroxide to form ethyl a -(21-dimethylaminoethyl)b -phenyl propionate and treating this with benzyl magnesium chloride. Pharmaceutical compositions useful as antihistamines comprise compounds of the invention in admixture or in conjunction with a pharmaceutical carrier. The compositions may be in a form suitable for oral, parenteral or topical administration, e.g. tablets, capsules, dragees, solutions, suspensions, emulsions, salves and creams, and may contain other therapeutically useful substances. An example is given of a tablet containing 3-benzyl-2-(21-dimethylaminoethyl)indene hydrochloride.
GB9814/59A 1958-03-20 1959-03-20 New 2-basically substituted indene compounds Expired GB912684A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US72264158A 1958-03-20 1958-03-20
US74432858A 1958-06-25 1958-06-25
US78531459A 1959-01-07 1959-01-07

Publications (1)

Publication Number Publication Date
GB912684A true GB912684A (en) 1962-12-12

Family

ID=27419038

Family Applications (1)

Application Number Title Priority Date Filing Date
GB9814/59A Expired GB912684A (en) 1958-03-20 1959-03-20 New 2-basically substituted indene compounds

Country Status (3)

Country Link
CH (3) CH394229A (en)
ES (1) ES247882A1 (en)
GB (1) GB912684A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004504394A (en) * 2000-07-10 2004-02-12 グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング Cyclic substituted aminomethyl compounds and medicaments containing the compounds

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004504394A (en) * 2000-07-10 2004-02-12 グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング Cyclic substituted aminomethyl compounds and medicaments containing the compounds

Also Published As

Publication number Publication date
CH391723A (en) 1965-05-15
ES247882A1 (en) 1959-12-16
CH391722A (en) 1965-05-15
CH394229A (en) 1965-06-30

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