SE313301B - - Google Patents

Info

Publication number
SE313301B
SE313301B SE11503/63A SE1150363DA SE313301B SE 313301 B SE313301 B SE 313301B SE 11503/63 A SE11503/63 A SE 11503/63A SE 1150363D A SE1150363D A SE 1150363DA SE 313301 B SE313301 B SE 313301B
Authority
SE
Sweden
Prior art keywords
formula
ethyl
group
compounds
amino
Prior art date
Application number
SE11503/63A
Inventor
Der Stelt C Van
Original Assignee
Koninklijke Pharma Fab 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 Pharma Fab Nv filed Critical Koninklijke Pharma Fab Nv
Publication of SE313301B publication Critical patent/SE313301B/xx

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
    • C07D219/02—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with only hydrogen, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/46—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic acid
    • C07C57/50—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic acid containing condensed ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
    • C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems 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 carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/78—Ring systems having three or more relevant rings
    • C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
    • C07D311/82—Xanthenes
    • C07D311/90—Xanthenes with hydrocarbon radicals, substituted by amino radicals, directly attached in position 9
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/18—Fluorenes; Hydrogenated fluorenes

Abstract

The invention comprises compounds of the formula <FORM:1006588/C2/1> wherein X1 and X each represent a hydrogen atom or together represent a single bond between the two carbon atoms, Y represents a single bond or an oxygen or sulphur atom or the group = NR2 (R2 representing a C1- 6 alkyl group or a hydrogen atom) or a -CH2-CH2- or -CH = CH- group and R1 represents a hydrogen or halogen atom or a C1- 6 alkyl group, and the non-toxic acid addition salts thereof. The preferred compounds are those in which X1, X, and R1 are hydrogen atoms. The compounds are prepared by a variety of methods (a) by condensing 1-phenyl-2-amino-propane with an aldehyde of the formula <FORM:1006588/C2/2> and reducing the azomethine bond in the resultant amino compound of the formula <FORM:1006588/C2/3> and, when X1 and X represent a single bond, optionally hydrogenating the double bono -CH = C<; the condensation may be affected under reducing conditions to give the amind compound directly; (b) by heating of 1-phenyl-2-amino-propane with an acid of the formula <FORM:1006588/C2/4> or the acid halide thereof, and reducing the carbonyl group of the resultant amide of the formula <FORM:1006588/C2/5> to a methylene group; (c) by reductive condensation of phenylacetone and an amine of the formula <FORM:1006588/C2/6> and (d) by the reaction of a compounds <FORM:1006588/C2/7> with a compound <FORM:1006588/C2/8> wherein one of A and B represents a primary amino group and the other represents a halogen atom. Examples describe the preparation of N - [2(10,11 - dihydro - 5H - dibenzo - [a,d]-cycloheptens - 5 - yl) - ethyl]-, N - [2 - (fluoren-9 - yl) - ethyl]-, N - [2 - (5H - dibenzo - [a,d]-cyclohepten - 5 - yl) - ethyl]-, N - [2 - (xanthen-9 - yl) - ethyl]-, N - [2 - (thioxanthen - 9 - yl)-ethyl]-and N - [2 - (9,19 - dihydro - 10 - methyl-acridin - 9 - yl) - ethyl] - 1 - phenyl - 2 - amino-propanes. A number of compounds of the above type wherein R1 is a C1- 6 alkyl, chloro and bromo group are specified. Aldehydes of the formula II may be prepared by condensing a ketone of the formula <FORM:1006588/C2/9> with acetylene to give the alcohol of the formula <FORM:1006588/C2/100> followed by isomerization in the presence of an acid. The aldehydes II may also be obtained by hydrolysis of the corresponding dialkylacetal. Carboxylic acids of the formula VIII are obtained by oxidation of the corresponding aldehyde II or, where X and X1 are hydrogen, by reacting an alcohol of the formula <FORM:1006588/C2/111> with malonic acid to yield a compound <FORM:1006588/C2/122> which is decarboxylated to the mono-acid by heating. The invention includes pharmaceutical compositions comprising at least one of the compounds of formula I, or a non-toxic acid addition salt thereof, which exhibit a dilating activity on the coronary blood vessels and which may be administered orally or parentally in the form of, e.g. tablets, pills, capsules, suspensions, emulsions, syrups, elixirs or unjectable preparations. Example 9 describes a composition in tablet form.
SE11503/63A 1962-10-19 1963-10-19 SE313301B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB39753/62A GB1006588A (en) 1962-10-19 1962-10-19 N-substituted-1-phenyl-2-aminopropanes

Publications (1)

Publication Number Publication Date
SE313301B true SE313301B (en) 1969-08-11

Family

ID=10411293

Family Applications (1)

Application Number Title Priority Date Filing Date
SE11503/63A SE313301B (en) 1962-10-19 1963-10-19

Country Status (12)

Country Link
US (1) US3359263A (en)
BE (1) BE638839A (en)
BR (1) BR6353836D0 (en)
CH (1) CH455754A (en)
DE (1) DE1214688B (en)
DK (2) DK109925C (en)
ES (1) ES292867A1 (en)
FI (2) FI42543B (en)
FR (2) FR1450391A (en)
GB (1) GB1006588A (en)
NL (2) NL133997C (en)
SE (1) SE313301B (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR145F (en) * 1964-06-01
US3452009A (en) * 1965-05-03 1969-06-24 Merck & Co Inc 2,3-epoxypropylidene derivative of 5h-dibenzo(a,d)-10,11-dihydrocycloheptenes
US4267192A (en) * 1980-03-11 1981-05-12 American Home Products Corporation Method for treating inflammation
FR2499556B1 (en) * 1981-02-10 1983-03-25 Cird
AU3172397A (en) * 1996-06-05 1998-01-05 Novartis Ag Anti-neurodegeneratively effective xanthene derivatives

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2676971A (en) * 1951-04-21 1954-04-27 Searle & Co Quaternary ammonium derivatives of aminoalkylxanthenes and aminoalkylthiaxanthenes
US3073847A (en) * 1959-02-12 1963-01-15 Hoffmann La Roche 9-(3-amino-1-propynyl) derivatives of 9-xanthenols and 9-thioxanthenols and a process for their preparation
NL274885A (en) * 1960-09-16
BE630063A (en) * 1962-03-23
US3258459A (en) * 1962-08-30 1966-06-28 Squibb & Sons Inc Method for the preparation of n-monosubstituted-secondary aminoalkyl derivatives of polycyclic compounds
US3264342A (en) * 1963-05-24 1966-08-02 Geigy Chem Corp Derivatives of 5h-dibenzo[a, d] cycloheptene
US3258488A (en) * 1963-08-12 1966-06-28 Colgate Palmolive Co Dibenzo[a, d]cycloheptene derivatives

Also Published As

Publication number Publication date
DK109925C (en) 1968-08-05
FI42543B (en) 1970-06-01
NL133997C (en)
BR6353836D0 (en) 1973-07-12
BE638839A (en)
NL299449A (en)
FR1450391A (en) 1966-06-24
DK111174B (en) 1968-06-24
CH455754A (en) 1968-05-15
US3359263A (en) 1967-12-19
ES292867A1 (en) 1964-04-01
DE1214688B (en) 1966-04-21
GB1006588A (en) 1965-10-06
FI44241B (en) 1971-06-30
FR3974M (en) 1966-03-07

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