• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
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    • 专利摘要:
    1460761 Dihalobenzylamines GEROTPHARMAZEUTIKA DR WALTER OTTO KG 2 Jan 1974 [2 Jan 1973 24 Aug 1973] 00141/74 Heading C2C Compounds of the general formula (X=halogen (not different); R 1 =H, alkyl; R 2 = alkyl, cycloalkyl, aryl, aralkyl or NR 1 R 2 = saturated heterocyclic group which may contain an oxygen, sulphur or further nitrogen (optionally substituted) atom; R 3 = alkyl, alkoxyalkyl, carboxyalkyl, carbamylalkyl, aralkyl, acyl, alkanesulphonyl, arenesulphonyl, cyanoalkyl, hydroxyalkyl, carbalkoxyalkyl, dialkylcarbamyl, alkylcarbamylalkyl, dialkylcarbamylalkyl, basic residue) and their salts with acids or bases are prepared by the Mannich reaction followed by etherification or esterification and/or conversion to a salt. Some of these compounds are diuretics and saluretics, and some have secretolytic activity. They may be administered in the form of pharmaceutical preparations containing them in association with a carrier.
    公开号:SU1091852A3
    申请号:SU741993871D
    申请日:1974-01-02
    公开日:1984-05-07
    发明作者:Х.Шлагер Лудвиг
    申请人:Герот Фармацойтика Гмбх (Фирма)；
    IPC主号:
    专利说明:

    11 The invention relates to a process for the preparation of new compounds, derivatives of 2-aminomethyl-4,6-dihalopropanol, which can be used in the pharmaceutical industry. In organic synthesis, the reaction of phenyl oximethylation with formaldehyde is well known, followed by the interaction of the reaction product with fl amines. However, there is no literature on the preparation of compounds derived from 2-aminomethyl-4, 6-dihalophenol, which have valuable properties. Most of the chlorohydrates of these compounds dissolve very easily in water as well as chloroform, i.e. these compounds have hydrophobic and hydrophilic properties. According to the invention, a method is described for the preparation of 2-aminomethyl-4,6-, dihalo-phenol derivatives of the total formula (I) where X is the same halogen atom; R. is hydrogen or lower alkyl; R is alkyl, cycloalkyl, aryl, arylalkyl or R, joined together with a nitrogen atom, form a saturated heterocyclic ring, which may also contain an oxygen, nitrogen or sulfur atom, RI is hydrogen, alkyl, alkoxyalkyl, carboxyalkyl, carbamylalkyl, arylalkyl, acyl, sulfonyl, alkali metal atom, cyanalkyl, hydroxylalkyl, carbalkoxyalkyl, H, M-dialkylcarbamyl, 5 N-alkylcarbamylalkyl or H, M-dialkylcarbamyl-alkyl, or their salts with acids or bases, consisting of 2.4, 4-ds, d-4-ds, or their salts with acids or bases; General formula (II) where X has specified the second value, is subjected to the reaction with formfordehyde and an amine of the general formula (III) where R -1 and Rj have the indicated values in an inert solvent and the resulting compound of the general formula (IV) CH -If is either converted to salt or subjected to FOT reactions with a compound of the general formula (V) YRg, where R has the indicated values, Y is a halogen atom, followed by isolation of the target products in a known manner. The process takes place in an inert solvent, for example, in hexamethylphosphoric triamide under mild conditions. Example 1. To a mixture cooled to 10 with 300 ml of a 35% formaldehyde solution and 2 liters of dioxane, 453 g of N-methylcyclohexylamine are added dropwise while transferring. Then, 1008 g of 2,4-dibromophenol is added, the mixture is heated at reflux for 3 hours, and then evaporated in vacuo to the syrupy consistency of the reaction mass. Brown syrup is diluted with methanol and, after seeding into the cooled solution, crystalline N- (2-oxy-3,5-dibromobenzyl) -Y-methylcyclohexylamine is obtained, which is washed on the filter with methanol, the freezing point (i.e. From the mother liquor, the hydrochloride of this compound was also removed by the action of an alcoholic solution of IP. The hydrochloride melts in the range of 182-186 after recrystallization from ethanol. Example 2. 100 g of the base obtained according to Example 1 are dissolved in 150 ml of dimethylformamide and added portionwise to 6.08 g of lithium amide while stirring, while the temperature of the mixture rises to 40 C. A colorless precipitate soon precipitates out of the clear solution. a powder that is phenol t lithium phenol N- (2-hydroxy-3, 5-dibromobenzyl) -H-mets1 cyclohexylamine with t.zastyv. 130 C. Example 3. To a solution of 200 g of the base prepared according to Example 1 in 600 ml of acetone, 150 ml of sodium methylate solution are added dropwise with stirring. Then the solution is evaporated under vacuum and the residue is stirred with ether, while crystallizing
    权利要求:
    Claims (2)
    [1]
    The method of obtaining derivatives
    [2]
    2-aminomethyl-4,6-dihaloid-phenol of the general formula where X are the same halogen atoms ;.
    - hydrogen or lower alkyl; Rj is alkyl, cycloalkyl, aryl, arylalkyl or R 1 and R , co. together with a nitrogen atom, form a saturated heterocyclic ring in which oxygen, nitrogen or sulfur atoms may also be present;
    Rj is hydrogen, alkyl, alkoxyalkyl, carboxyalkyl, carbamylalkyl, arylalkyl, acyl, sulfonyl, an alkali metal atom, cyanoalkyl, hydroxyalkyl, carbalkoxyalkyl, Ν, Ν-dialkylcarbamyl, N-alkylcarbamylalkyl or Ν, их, or bases, characterized in that the 2,4-dihalo-phenol of the general formula where X has the indicated 'meaning., react with formaldehyde and an amine of the general formula g ~ n where they have the indicated meanings, in an inert solvent and the resulting compound either subject to interacting with a compound of the general formula YRj, where Rg has the indicated meanings, Y is a halogen atom, or is isolated in a known manner as a base or salt.
    Priority by signs:
    02.01.73 when Rj is hydrogen, alkyl, alkoxyalkyl, carboxyalkyl, carbamylalkyl, arylalkyl, acyl, sulfonyl, an alkali metal atom;
    24108.73 when-Rj is cyanoalkyl, hydroxylalkyl, carbalkoxyalkyl, Ν, алки dialkylcarbamyl ^ N is alkylcarbamylalkyl or Ν, Ν-dialkylcarbamylalkyl.
    类似技术:
    公开号 | 公开日 | 专利标题
    SU1091852A3|1984-05-07|Process for preparing derivatives of 2-aminomethyl-4,6-dihaloidophenol or their salts
    US2748122A|1956-05-29|2-anilino-4, 6-dimethylpyrimidines
    US4563469A|1986-01-07|Derivatives of N-[2-|-yl)ethyl]amine as cognition activators
    US3963735A|1976-06-15|Acylated 2-aminothiazole derivatives
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    US3985898A|1976-10-12|Thiourea derivatives
    PL95737B1|1977-11-30|METHOD OF MAKING NEW / TIAZOLILO-2 / ALKANOCARBONAMIDE
    US3971782A|1976-07-27|Fluorene derivatives
    SU571187A3|1977-08-30|Method of obtaining derivatives of 2-aminomethyl-4,6-digahaloidophenol derivatives
    US3931244A|1976-01-06|Thioureas
    US4226799A|1980-10-07|α-Aminomethylene-β-formylaminopropionitrile and its manufacture
    US3821231A|1974-06-28|Method for preparation of n-substituted 4-aniline piperidines
    US4278685A|1981-07-14|Amide derivatives
    US4086352A|1978-04-25|Certain 6-aryloxy-2-oxo-1-aza-4-thia-spiro[4,5]decanes
    US3973025A|1976-08-03|1,4-Dihydro-3,5-pyridine dicarbonitrile derivatives
    US3378592A|1968-04-16|Process for the production of 3, 4-dihydroxybenzyloxyaminehydrobromide
    US3268533A|1966-08-23|4-aminophenylcyclopropyl ketones
    US3925360A|1975-12-09|2-Benzyl aziridines
    同族专利:
    公开号 | 公开日
    DE2364191A1|1974-07-11|
    CH610292A5|1979-04-12|
    DE2364191C2|1986-06-12|
    NL7317753A|1974-07-04|
    DD113526A5|1975-06-12|
    BG24226A3|1978-01-10|
    CA1090340A|1980-11-25|
    NL167414B|1981-07-16|
    US3996278A|1976-12-07|
    DK309774A|1975-04-28|
    NL167414C|1981-12-16|
    ATA738773A|1976-02-15|
    AT332863B|1976-10-25|
    JPS5335065B2|1978-09-25|
    BE824138R|1975-07-07|
    SE420716B|1981-10-26|
    CS183634B2|1978-07-31|
    JPS49100043A|1974-09-20|
    GB1460761A|1977-01-06|
    FR2212145A1|1974-07-26|
    AU7087774A|1976-01-08|
    FR2212145B1|1977-01-28|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    US2806063A|1956-04-23|1957-09-10|Dow Chemical Co|Amine salts of chlorophenols|
    BE562425A|1956-11-16|
    US3227756A|1962-07-10|1966-01-04|Velsicol Chemical Corp|N,n-mono- and di-substituted-aralkyl amines|
    US3809721A|1970-12-23|1974-05-07|Merck & Co Inc|Substituted 2-aminomethyl-4,6-disubstituted phenols|
    US3864401A|1970-12-23|1975-02-04|Merck & Co Inc|Substituted 2-aminomethyl-4,6-dihalophenols|
    NL180978C|1972-10-23|1987-06-01|Thomae Gmbh Dr K|METHOD FOR MANUFACTURING A PHARMACEUTICAL PREPARATION WITH SECRETORIC AND / OR ANTI-COUGHTING ACTION, AND A METHOD FOR PREPARING A COMPOUND SUITABLE FOR USE IN THE FOREGOING METHOD|FR2287219B2|1974-10-11|1978-12-22|Gerot Pharmazeutika|
    WO1980000561A1|1978-09-06|1980-04-03|Sandoz Ag|Alpha-alkyl-o-oxy-benzylamin derivatives,preparation thereof and remedies containing them|
    CA1219587A|1981-12-14|1987-03-24|Norman P. Jensen|Hydroxybenzylaminobenzenes as anti-inflammatoryagents|
    US4578390A|1981-12-14|1986-03-25|Merck & Co., Inc.|Hydroxybenzylamino derivatives as anti-inflammatory agents|
    FR2661176B1|1990-04-20|1992-06-12|Adir|NEW PROCESS FOR THE PREPARATION OF 1-PIPERAZINE IN REDUCTIVE AMINATION.|
    ZA923283B|1991-05-29|1993-01-27|Akzo Nv|Phenoxyphenyl derivatives|
    BRPI0415874A|2003-11-10|2007-01-09|Schering Ag|benzyl ether amine compounds as ccr-5 antagonists|
    CN103833588B|2012-11-16|2015-09-23|上海医药工业研究院|Two kinds of crystal formations, preparation method and application thereof of amides|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    AT173A|AT319915B|1973-01-02|1973-01-02|Process for the preparation of new 2-aminomethyl-4,6-dihalophenol derivatives and their salts with physiologically compatible acids or bases|
    AT738773A|AT332863B|1973-01-02|1973-08-24|PROCESS FOR THE PREPARATION OF NEW 2-AMINOMETHYL-4,6-DIHALOGENPHENOL DERIVATIVES AND THEIR ADDITIONAL SALTS WITH ACIDS|
    BE824138|1975-01-06|
    BE152177A|BE824138R|1973-01-02|1975-01-06|PROCESS FOR THE PREPARATION OF NEW DERIVATIVES OF AMINOMETHYL-2 DIHALO-4,6-PHENOL|
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