GB962793A - Improvements in or relating to pharmacologically active compounds being substituted tryptamines - Google Patents

Improvements in or relating to pharmacologically active compounds being substituted tryptamines

Info

Publication number
GB962793A
GB962793A GB24105/60A GB2410560A GB962793A GB 962793 A GB962793 A GB 962793A GB 24105/60 A GB24105/60 A GB 24105/60A GB 2410560 A GB2410560 A GB 2410560A GB 962793 A GB962793 A GB 962793A
Authority
GB
United Kingdom
Prior art keywords
compound
formula
alkyl
reacting
prepared
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
GB24105/60A
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 Philips NV
Original Assignee
Philips Gloeilampenfabrieken 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 Philips Gloeilampenfabrieken NV filed Critical Philips Gloeilampenfabrieken NV
Publication of GB962793A publication Critical patent/GB962793A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
    • A61K31/404—Indoles, e.g. pindolol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
    • A61K31/404—Indoles, e.g. pindolol
    • A61K31/405—Indole-alkanecarboxylic acids; Derivatives thereof, e.g. tryptophan, indomethacin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
    • C07D209/16—Tryptamines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Abstract

<FORM:0962793/C1/1> <FORM:0962793/C1/2> <FORM:0962793/C1/3> <FORM:0962793/C1/4> <FORM:0962793/C1/5> The invention comprises compounds of formula I and acid addition salts thereof in which R1 represents an hydroxyl group or an etherified hydroxyl group n is 0, 1, 2 or 3, R2 is a C3-8- alkyl group in which at least one hydrogen atom is replaced by a hydroxyl or an etherified or esterified hydroxyl group, and R3 is a hydrogen atom or a C1-8 alkyl group, with or without one or more hydroxyl or etherified or esterified hydroxyl groups substituted for one or more hydrogen atoms in such alkyl groups; the preparation thereof either by alkylating a compound of formula II especially with reacting the amino compound with a compound R2X (where X is a halogen atom) or with a carboxylic acid halide or anhydride comprising an acyl residue convertible by reduction to such radical R2 and where one reactant consists of such acid halide or anhydride, reducing the reaction product with a metal or metal alkyl hydride; or by reacting a compound of formula III with an aliphatic amine which is substituted by one or more esterified or etherified hydroxyl groups or by groups which, after the alkylation reaction, are replaced by esterified or etherified hydroxyl groups or when the first named reactant is a compound of the formula III except that the hydrogen atoms at one or each of the C atoms in the 3-ethyl group are replaced by oxygen, reducing the reaction product after alkylation with a metal or metal alkyl halide; or by reacting a compound of formula II with a compound of formula IV (where Hlg represents a chloride or bromine atom and R5 represents an alkyl group and n is 1 to 6 and reducing the semi-ester-semi-amide to an amino alcohol with a metal hydride or metal alkyl hydride; or by reacting a compound of formula II with a compound of formula X (wherein n1 is 2 to Y) and reducing the resulting ester to the alcohol; or with a compound Hlg(CH2)n11-O-R4 in which R4 is an alkyl, aryl or aryl or an acyl group, and n11 is 3 to 8. Benzyl ethers are hydrogenated to the free hydroxy compounds. 3-(2-Ethylaminoethyl)indole is prepared by reacting 3-(2-aminoethyl)indole with acetic anhydride and reducing the resulting 3-(2-acetamidoethyl)indole. Similarly are prepared 3-(2-R-aminoethyl)indoles where R is propyl, butyl isobutyl, amyl and isoamyl, 3-(2-ethylaminoethyl)-5-methoxy-5-benzyloxy- and 5, 6-dimethoxy-indoles through the corresponding acetyl derivatives. 1-Benzyloxy-5-bromopentane is prepared from benzyl alcohol and 1, 5-dibromopentane. 5-Methoxyindolylglyoxylic acid chloride-3 is prepared from 5-methoxyindole and oxalyl chloride. N-Ethylaminosuccinic acid dimethyl ester is prepared from dimethyl maleate and ethylamine. 2-Nitrophenetidine is diazotized and reacted with formaldoxime to give 4-ethoxy-2-nitrobenzaldehyde which is reacted with nitromethane to give 4-ethoxy-2-b -dinitrostyrene, the last named is hydrogenated to give 6-ethoxyindole and converted into 6-ethoxy indolylgyoxylic acid chloride-3 with oxalyl chloride. Pharmaceutical compositions contain at least one of the compounds of the invention and may be in the form of tablets or solutions for injection.
GB24105/60A 1959-07-13 1960-07-11 Improvements in or relating to pharmacologically active compounds being substituted tryptamines Expired GB962793A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
NL241228 1959-07-13

Publications (1)

Publication Number Publication Date
GB962793A true GB962793A (en) 1964-07-01

Family

ID=19751827

Family Applications (1)

Application Number Title Priority Date Filing Date
GB24105/60A Expired GB962793A (en) 1959-07-13 1960-07-11 Improvements in or relating to pharmacologically active compounds being substituted tryptamines

Country Status (3)

Country Link
ES (1) ES259580A1 (en)
FR (1) FR705M (en)
GB (1) GB962793A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NZ208337A (en) * 1983-06-10 1988-10-28 Bristol Myers Co 2-(2-hydroxy-3-((2-(ar-hydroxy-1h-aminopropoxy-yl)ethyl benzonitriles and pharmaceutical compositions

Also Published As

Publication number Publication date
FR705M (en) 1961-07-31
ES259580A1 (en) 1961-01-16

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