GB1006588A - N-substituted-1-phenyl-2-aminopropanes - Google Patents

N-substituted-1-phenyl-2-aminopropanes

Info

Publication number
GB1006588A
GB1006588A GB39753/62A GB3975362A GB1006588A GB 1006588 A GB1006588 A GB 1006588A GB 39753/62 A GB39753/62 A GB 39753/62A GB 3975362 A GB3975362 A GB 3975362A GB 1006588 A GB1006588 A GB 1006588A
Authority
GB
United Kingdom
Prior art keywords
formula
ethyl
group
compounds
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
GB39753/62A
Inventor
Cornelius Van Der Steit
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
Priority to BE638839D priority Critical patent/BE638839A/xx
Priority to NL299449D priority patent/NL299449A/xx
Priority to NL133997D priority patent/NL133997C/xx
Application filed by Koninklijke Pharmaceutische Fabrieken NV filed Critical Koninklijke Pharmaceutische Fabrieken NV
Priority to GB39753/62A priority patent/GB1006588A/en
Priority to US302707A priority patent/US3359263A/en
Priority to FI2027/63A priority patent/FI42543B/fi
Priority to BR153836/63A priority patent/BR6353836D0/en
Priority to DEN23907A priority patent/DE1214688B/en
Priority to FR951049A priority patent/FR1450391A/en
Priority to DK493363AA priority patent/DK109925C/en
Priority to CH1280863A priority patent/CH455754A/en
Priority to ES0292867A priority patent/ES292867A1/en
Priority to SE11503/63A priority patent/SE313301B/xx
Priority to FR960756A priority patent/FR3974M/fr
Publication of GB1006588A publication Critical patent/GB1006588A/en
Priority to DK90066AA priority patent/DK111174B/en
Priority to FI2232/69A priority patent/FI44241B/fi
Expired legal-status Critical Current

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.
GB39753/62A 1962-10-19 1962-10-19 N-substituted-1-phenyl-2-aminopropanes Expired GB1006588A (en)

Priority Applications (16)

Application Number Priority Date Filing Date Title
BE638839D BE638839A (en) 1962-10-19
NL299449D NL299449A (en) 1962-10-19
NL133997D NL133997C (en) 1962-10-19
GB39753/62A GB1006588A (en) 1962-10-19 1962-10-19 N-substituted-1-phenyl-2-aminopropanes
US302707A US3359263A (en) 1962-10-19 1963-08-16 Nu-substituted-1-phenyl-2-aminopropanes
FI2027/63A FI42543B (en) 1962-10-19 1963-10-17
DEN23907A DE1214688B (en) 1962-10-19 1963-10-18 Process for the preparation of N-substituted 1-phenyl-2-aminopropanes and their non-toxic acid addition salts
BR153836/63A BR6353836D0 (en) 1962-10-19 1963-10-18 PROCESS OF PREPARATION OF N-SUBSTITUTES-1-PHENYL-2-AMINO PROPANS
FR951049A FR1450391A (en) 1962-10-19 1963-10-18 N-substituted 1-phenyl-2-aminopropanes and process for their preparation
DK493363AA DK109925C (en) 1962-10-19 1963-10-18 Process for the preparation of N-substituted 1-phenyl-2-aminopropanes or acid addition salts thereof.
CH1280863A CH455754A (en) 1962-10-19 1963-10-18 Process for the preparation of N-substituted 1-phenyl-2-aminopropanes
ES0292867A ES292867A1 (en) 1962-10-19 1963-10-18 Nu-substituted-1-phenyl-2-aminopropanes
SE11503/63A SE313301B (en) 1962-10-19 1963-10-19
FR960756A FR3974M (en) 1962-10-19 1964-01-17
DK90066AA DK111174B (en) 1962-10-19 1966-02-21 Process for the preparation of N-substituted 1-phenyl-2-aminopropanes or acid addition salts thereof.
FI2232/69A FI44241B (en) 1962-10-19 1969-07-28

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
GB1006588A true GB1006588A (en) 1965-10-06

Family

ID=10411293

Family Applications (1)

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

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)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0035903A1 (en) * 1980-03-11 1981-09-16 American Home Products Corporation Dibenzocycloheptenylidenes and their use in pharmaceutical compositions

Families Citing this family (4)

* 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
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

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0035903A1 (en) * 1980-03-11 1981-09-16 American Home Products Corporation Dibenzocycloheptenylidenes and their use in pharmaceutical compositions

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
SE313301B (en) 1969-08-11
US3359263A (en) 1967-12-19
ES292867A1 (en) 1964-04-01
DE1214688B (en) 1966-04-21
FI44241B (en) 1971-06-30
FR3974M (en) 1966-03-07

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