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WO1991011439A1 - Derives de 4-amino-3-imidazoline-1-oxyle et leur procede de preparation - Google Patents

Derives de 4-amino-3-imidazoline-1-oxyle et leur procede de preparation Download PDF

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Publication number
WO1991011439A1
WO1991011439A1 PCT/SU1990/000026 SU9000026W WO9111439A1 WO 1991011439 A1 WO1991011439 A1 WO 1991011439A1 SU 9000026 W SU9000026 W SU 9000026W WO 9111439 A1 WO9111439 A1 WO 9111439A1
Authority
WO
WIPO (PCT)
Prior art keywords
imidazoline
oxyl
derivatives
amino
compounds
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.)
Ceased
Application number
PCT/SU1990/000026
Other languages
English (en)
Russian (ru)
Inventor
Leonid Borisovich Volodarsky
Vladimir Vladimirovich Martin
Tatyana Alexeevna Berezina
Lev Moiseevich Vainer
Valery Vladimirovich Khramtsov
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.)
Novosibirsky Institut Organicheskoi Khimii Sibirskogo Otdelenia
Institut Khimicheskoi Kinetiki I Gorenia Akademii Nauk Sssr
Original Assignee
Novosibirsky Institut Organicheskoi Khimii Sibirskogo Otdelenia
Institut Khimicheskoi Kinetiki I Gorenia Akademii Nauk Sssr
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 Novosibirsky Institut Organicheskoi Khimii Sibirskogo Otdelenia, Institut Khimicheskoi Kinetiki I Gorenia Akademii Nauk Sssr filed Critical Novosibirsky Institut Organicheskoi Khimii Sibirskogo Otdelenia
Priority to PCT/SU1990/000026 priority Critical patent/WO1991011439A1/fr
Publication of WO1991011439A1 publication Critical patent/WO1991011439A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D233/44—Nitrogen atoms not forming part of a nitro radical
    • C07D233/48—Nitrogen atoms not forming part of a nitro radical with acyclic hydrocarbon or substituted acyclic hydrocarbon radicals, attached to said nitrogen atoms
    • 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
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D233/44—Nitrogen atoms not forming part of a nitro radical
    • C07D233/50—Nitrogen atoms not forming part of a nitro radical with carbocyclic radicals directly attached to said nitrogen atoms

Definitions

  • the inventive invention is related to the Russian Federation’s 5-mines, and more precisely, to the new 4-amine-Z-imidazoline- ⁇ -oxo compounds and the case thereof.
  • connection 15 ghetical values of ⁇ , that is, having a value of ⁇ and ⁇ - order of 5-7 units.
  • the connection must be close to the central center and the main load.
  • ⁇ At the same time, the low-intensity radical center is a strong elec- tron
  • Amidine was found to be 25 nits, a series of strong nitric radicals of imidazoline - 4-plus-2,2,5,5-compound-l-3-imidazoline- ⁇ -oxyl having ⁇ and ⁇ réelle ⁇ Play ⁇ Play ⁇ Play 6. 6. "( ⁇ . ⁇ . ⁇ Kai-ne ⁇ , I. ⁇ . Grigoriev, ⁇ . ⁇ . ⁇ eznikov, G.I. Shchukin, ⁇ .B. Belgorodsky J.Ph. Chem., ⁇ .4, 1985, pp. 237).
  • 4-amin ⁇ -2,2,5,5- ⁇ e ⁇ ame ⁇ il-W-imidaz ⁇ zhn- ⁇ - ⁇ sil m ⁇ zhe ⁇ is ⁇ lz ⁇ va ⁇ sya only ⁇ aches ⁇ ve sgosh ⁇ v ⁇ g ⁇ z ⁇ nda, ⁇ s ⁇ l ⁇ u e ⁇ s ⁇ edinenie not imee ⁇ in m ⁇ le ⁇ ule ⁇ un ⁇ tsi ⁇ - 5 nalny ⁇ g ⁇ u ⁇ sh, delayuschi ⁇ eg ⁇ subs ⁇ a ⁇ m ⁇ e ⁇ men ⁇ v, lib ⁇ ⁇ bes ⁇ echivayuschi ⁇ ⁇ valen ⁇ n ⁇ e binding to biomolecules. Otherwise, this connection has a poor performance and poor performance, and, as noted above, the case is very good.
  • the inventive compounds provide yellow solid materials with a temperature-controlled melting point of 30-230 ° C, which are non-volatile.
  • the structure of the compounds is proved by the data of Y ⁇ , U ⁇ , EP ⁇ spectroscopy and elemental analysis.
  • the claimed compounds are effective compounds that can be used and can be used as an analysis of reagents, inhibitors and anti-drugs.
  • the process for the production of 4-amine-3-imidazoline- ⁇ -oxyl derivatives is in the process and is carried out by the following process.
  • the extract is dried with magnesium sulfate, evaporates. 5 ⁇ in case of the valuation of the commercial supplier at the stage of the interaction of the original reactants, the transmitter removes the transmitter from the
  • the extract is dried with magnesium sulfate, evaporates.
  • the discharge is supported by a silica gel column, the eluent is by cold. 25 1.39 g of 2,2,5,5-tetra-methyl-4-phenylamine-3-imidazoline- ⁇ -oxyl are obtained. ⁇ Play 6 ⁇ .
  • Example 2 35% 1.57 g (0.01 mol) 2,2,5,5-tetramethyl-3- -imidazoline-3-oxide- ⁇ -oxyl in 10 ml of diluted 1.6 ml ( 0.015 moles) is phenylocyanate and lasts for 12 hours at a temperature of 20 ° 0. Further reactive ⁇ ⁇ 91/11439 - 7 - ⁇ / ⁇ 90 / 00026
  • the inventive compounds were tested in sensitive quantities of sensitive blue probes and tags.
  • the spectral binding constant of, for example, 2,2,5,5-tetramethyl-4- ( Mr-naphthyl) amine-3-imidazoline- ⁇ - ⁇ -35 strength with a minimum of 450 cyme was shared.
  • inventive materials may be used in chemistry as antioxidants and drugs, and in biology and medicine as susceptible substances.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

Nouveaux composés, dérivés de 4-amino-3-imidazoline-1-oxyle ayant la formule générale (I) dans laquelle R = C6H5, I-C10H7, C2H5, C4H9, CH2CH2Cl ClC6H4. Un procédé d'obtention desdits composés consiste en une interaction entre 2,2,5,5-tétraméthyle-3-imidazoline-3-oxyde-1-oxyle et des isocyanates de la formule générale RNCO, dans laquelle R = C6H5, ClC6H4, I-C10H7, C2H5, C4H9, CH2CH2Cl. Le rapport molaire entre les composants est de 1:1,5 à 15,0, respectivement. Le procédé est mis en ÷uvre à une température comprise entre 20 et 50 °C. En résultat, on obtient une masse de réaction que l'on traite ensuite à l'aide d'une solution aqueuse alcoolique d'alkali.
PCT/SU1990/000026 1990-01-24 1990-01-24 Derives de 4-amino-3-imidazoline-1-oxyle et leur procede de preparation Ceased WO1991011439A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/SU1990/000026 WO1991011439A1 (fr) 1990-01-24 1990-01-24 Derives de 4-amino-3-imidazoline-1-oxyle et leur procede de preparation

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/SU1990/000026 WO1991011439A1 (fr) 1990-01-24 1990-01-24 Derives de 4-amino-3-imidazoline-1-oxyle et leur procede de preparation

Publications (1)

Publication Number Publication Date
WO1991011439A1 true WO1991011439A1 (fr) 1991-08-08

Family

ID=21617647

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/SU1990/000026 Ceased WO1991011439A1 (fr) 1990-01-24 1990-01-24 Derives de 4-amino-3-imidazoline-1-oxyle et leur procede de preparation

Country Status (1)

Country Link
WO (1) WO1991011439A1 (fr)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SU397516A1 (fr) * 1971-03-15 1973-09-17
SU412193A1 (fr) * 1971-04-05 1974-01-25
SU420627A1 (ru) * 1971-05-03 1974-03-25 Л. Б. Володарский , Т. К. Севасть нова Способ получения производных 2,2,5,5- тетразамещенных з-имидазолин-1-оксилов
US3927019A (en) * 1971-02-22 1975-12-16 Synvar Ass 1-Oxylimidazolinyl compounds used as stable free radical pH indicators
US4328349A (en) * 1980-10-08 1982-05-04 Sk&F Lab Co. Process for preparing 5-methyl-4-imidazolecarboxylic acid esters

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3927019A (en) * 1971-02-22 1975-12-16 Synvar Ass 1-Oxylimidazolinyl compounds used as stable free radical pH indicators
SU397516A1 (fr) * 1971-03-15 1973-09-17
SU412193A1 (fr) * 1971-04-05 1974-01-25
SU420627A1 (ru) * 1971-05-03 1974-03-25 Л. Б. Володарский , Т. К. Севасть нова Способ получения производных 2,2,5,5- тетразамещенных з-имидазолин-1-оксилов
US4328349A (en) * 1980-10-08 1982-05-04 Sk&F Lab Co. Process for preparing 5-methyl-4-imidazolecarboxylic acid esters

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