FI43439C - Method for the preparation of alpha-alkyl tyronines affecting the serum cholesterol pattern - Google Patents

Method for the preparation of alpha-alkyl tyronines affecting the serum cholesterol pattern

Info

Publication number
FI43439C
FI43439C FI650814A FI81465A FI43439C FI 43439 C FI43439 C FI 43439C FI 650814 A FI650814 A FI 650814A FI 81465 A FI81465 A FI 81465A FI 43439 C FI43439 C FI 43439C
Authority
FI
Finland
Prior art keywords
compound
general formula
methylhydantoin
diiodo
acylated
Prior art date
Application number
FI650814A
Other languages
Finnish (fi)
Other versions
FI43439B (en
Inventor
Hillmann Guenther
Hillmann Anneliese
Beckmann Ruediger
Hoenen Lambert
Original Assignee
Gruenenthal Chemie
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 Gruenenthal Chemie filed Critical Gruenenthal Chemie
Application granted granted Critical
Publication of FI43439B publication Critical patent/FI43439B/fi
Publication of FI43439C publication Critical patent/FI43439C/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C07C229/36—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings with at least one amino group and one carboxyl group bound to the same carbon atom of the carbon skeleton
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • A61K38/22—Hormones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
    • C07D233/72—Two oxygen atoms, e.g. hydantoin
    • C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
    • C07D233/78—Radicals substituted by oxygen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Immunology (AREA)
  • Medicinal Chemistry (AREA)
  • Zoology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Endocrinology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Novel compounds of the general formula <FORM:1100643/C2/1> (wherein R1 represents a C1- 6 alkyl radical, R2 represents an NH2 or acylated NH2 group, and R3, R4 and R5, which may be the same or different, represent H or I atoms) are prepared by (a) reacting a compound of the general formula <FORM:1100643/C2/2> (wherein R6 and R7 jointly represent -NH-CO-NH- or R6 represents OH or etherified OH and R7 represents NH2 or acylated NH2) with an acid of the general formula <FORM:1100643/C2/3> at substantially neutral pH under anaerobic or aerobic conditions at temperatures below 100 DEG C. and, if necessary, converting R6 and R7 to OH and NH2, or (b) reacting a compound II (but in which R7 is not NH2) with a compound of the general formula <FORM:1100643/C2/4> (wherein R9 represents in alkyl radical and An an anion) in a solvent in the presence of a basic substance, removing the solvent, removing R9 by acid hydrolysis, hydrolysing the hydantoin (when R6 + R7 = -NH-CO-NH-) by warming with dilute aqueous alkaline or mineral acid solutions, and mono- or di-iodinating the product, preferably in alkaline solution, or (c) reacting an activated ester of a compound of the general formula <FORM:1100643/C2/5> (wherein R6 and R8 jointly represent -NH-CO-NH- or R6 represents OH or etherified OH and R8 represents an acylamino group) with a compound of the general formula <FORM:1100643/C2/6> in the presence of a solvent and/or a base, replacing the NO2 groups by R3 and R4 via NH2 and diazo groups and completing the process as in (b), omitting the iodination step when using a compound XI. The products may be converted into salts with inorganic or organic acids or bases, and a free NH2 group in the products may be acylated. The preparation of the following starting materials and intermediates is described: 5 - (31 - iodo - p - hydroxybenzyl) - 5 - methylhydantoin, 5 - (31,51 - dinitro -, - diamino - and - diiodo - 41 - p - methoxyphenoxybenzyl) - 5 - methylhydantoin, 5 - (31,51 - diiodo - 41 - p-hydroxyphenoxybenzyl) - 5 - methylhydantoin, and 3,5 - diiodo - a - methylthyromine (and its sodium salt). Reference has been directed by the Comptroller to Specification 1,047,082.
FI650814A 1964-04-10 1965-04-05 Method for the preparation of alpha-alkyl tyronines affecting the serum cholesterol pattern FI43439C (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEC0032613 1964-04-10

Publications (2)

Publication Number Publication Date
FI43439B FI43439B (en) 1970-12-31
FI43439C true FI43439C (en) 1971-04-13

Family

ID=7020410

Family Applications (1)

Application Number Title Priority Date Filing Date
FI650814A FI43439C (en) 1964-04-10 1965-04-05 Method for the preparation of alpha-alkyl tyronines affecting the serum cholesterol pattern

Country Status (13)

Country Link
AT (3) AT268547B (en)
BE (1) BE662271A (en)
BR (1) BR6568876D0 (en)
CH (1) CH469664A (en)
DE (1) DE1793776A1 (en)
DK (1) DK123229B (en)
ES (1) ES311669A1 (en)
FI (1) FI43439C (en)
FR (1) FR1587317A (en)
GB (1) GB1100643A (en)
NL (1) NL142402B (en)
OA (1) OA01689A (en)
SE (1) SE332994B (en)

Also Published As

Publication number Publication date
BR6568876D0 (en) 1973-08-07
NL6503266A (en) 1965-10-11
CH469664A (en) 1969-03-15
DE1793776A1 (en) 1974-08-29
FI43439B (en) 1970-12-31
DK123229B (en) 1972-05-29
OA01689A (en) 1969-12-15
ES311669A1 (en) 1965-07-01
SE332994B (en) 1971-03-01
NL142402B (en) 1974-06-17
BE662271A (en) 1965-10-08
AT268553B (en) 1969-02-10
GB1100643A (en) 1968-01-24
FR1587317A (en) 1970-03-20
AT268552B (en) 1969-02-10
AT268547B (en) 1969-02-10

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