• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
  • 法律状态
  • 优先权
    • 专利摘要:

    公开号:SU828963A3
    申请号:SU792836799
    申请日:1979-11-06
    公开日:1981-05-07
    发明作者:Блаттнер Ханс；Сторни Анжело
    申请人:Циба-Гейги Аг (Фирма)；
    IPC主号:
    专利说明:

    Union of Soviet
    Socialist
    Republics
    DESCRIPTION
    Inventions
    TO PATENT "" 828963
    USSR State Committee for Inventions · and Discoveries (61) Additional to the patent - (22) Declared 06.1179 (21, 2836799 / 23-04 (23) Priority - (32) 10.1178 (31) 11588/78 (33) Switzerland
    Published 07.05.81 Bulletin No. 17
    Date of publication of the description 07.05.81 (5f) M. Cl. 3
    C 07 D 223/22 // k 61 K 31/55 (53) UDC 547 891 '.2.07 (088.8) (72) Authors of the invention (71) Applicant
    Foreigners
    Hans Blattner and Angelo Storni. (Switzerland)
    Foreign company '’Qiba-Geigy AG' (Switzerland)
    (54) METHOD FOR PRODUCING 10-CYAN-5H-DIBENZ_ (b, f) ~ AZEPIN-5-CARBOXYAMIDE
    The invention relates to the production of a new dibenzazepine derivative having biological activity, which can be used in medicine.
    A method for producing amides by the interaction of acid chlorides with ammonia is widely described in the literature [11.
    . The aim of the invention is to develop, on the basis of the known method of a method for producing a new compound having valuable and pharmacological properties, namely anticonvulsant activity.
    The goal is achieved ’’ is described by a process for the preparation of 10cyan-5H-dibenz- / b, f / -azepine-5-carboxyamide by reacting a compound of the formula
    where X is a halogen with ammonia in an organic solvent; thirty
    Halogen is bromine or iodine, but especially chlorine.
    The reaction is preferably carried out in an organic solvent, for example a lower alcohol such as ethanol, iopropanol or butanol, in a liquid such as an ether, such as tetrahydrofuran or dioxane, in a hydrocarbon such as benzene or toluene, at room temperature or preferably when heated, for example, at the boiling point used solvent.
    The ammonia required for the reaction can be introduced in the form of a gas at the beginning or in the bottom of the whole reaction or by using a solvent miscible with water, or in the form of a concentrated aqueous solution. But it is also possible to use liquid ammonia and carry out the conversion, as necessary, in a closed apparatus.
    Example 1. 21.8 g (0.1 mol) of 10-cyan-5H-dibene- / b, f / -azepine are added with stirring to a solution of '19, 8 g of phosgene (0.2 mol) in 700 ml absolute toluene. The mixture is stirred for 30 hours at a temperature in the reaction mixture of 50-53 ° C. Then the reaction mixture was evaporated to dryness in a rotational evaporator, with the remainder of the crude 10-cyan remaining: 5H-dibenz- / L, f / -azepine-5-carbonyl chloride with mp. 148-153 ° C. ·
    The resulting crude product is dissolved with stirring at 70 ° C. in 600 ml of absolute ethanol. Ammonia gas was passed into this solution for ^ 2 hours. In this case, the reaction solution is constantly boiled with reflux. The reaction mixture was evaporated on a rotary evaporator, the residue was washed with water and recrystallized 10-cyano-5H-dibenz / b, f / azepine-5-carboxyamide after drying from toluene t.pl.212-215 in C. The starting material can oyt obtained as follows.
    27.2 g (0.1 mol) 10-brOhm-5H-di-. benz- / b, f / -azepine, 10.7 g (0.12 mol) of copper cyanide [1] and 50 ml of dimethylformamide are heated with stirring for −20 1 1/2 hours at a bath temperature of 150 ° C.
    R
    Then the reaction mixture was cooled at 40 ° С, stirred vigorously for 2 h with 200 ml of a 50% aqueous solution of ethylenediamine and 200 ml of methylene chloride. Then, the organic phase is separated and the aqueous phase is extracted two more times. 100 ml of methylene chloride are extracted.
    The combined organic solutions were washed with water, dried with sodium sulfate and evaporated. The remainder of 10-cyan5H-dibenz- / b, £ / -azepine, is recrystallized from ethanol and melted at 143-145 ° C,
    权利要求:
    Claims (1)
    [1]
    (54) METHOD OF OBTAINING U-CYAN-5H-DIBENZ- (b, f; - AZEPIN-5-CARBOXYAMIDE: a evaporator, leaving a residue of the crude 10-cyan: 5H-di-en- / b, f / -azepine -5-carbonyl; chloride with mp 148-153c; The crude product obtained is dissolved in 600 ml of absolute ethanol with stirring. Ammonia-gas is passed into this solution for 2 h. The reaction solution is boiled all the time. The reaction mixture is evaporated on a rotary evaporator, the residue is washed with water and 10-cyan-5H-dibenz (b, f / -azepine-5-carboxyamide is recrystallized after drying from toluene, mp. 212-215 ° C. The starting product can be obtained as follows: 27.2 g (0.1 mol) U-brOm-BN-DI benzo / b, / - aepepine, 10 , 7 g (0.12 mol of copper cyanide 1 and 50 ml of dimethyl form amide with stirring is heated for 1 1/2 hours at the bath temperature. Then the reaction mixture is cooled p, about 40 s, vigorously stirred for 2 hours with 200 ml of 50% -nO : an aqueous solution of ethylenediamine and 200 ml of methylene chloride. The organic phases are then separated and the aqueous phase is extracted twice more with 100 ml of methylene chloride. The combined organic solutions are washed with water, dried over sodium sulfate and evaporated. A 10-cyan5H-dibene- (b, l) -azepine residue was recrystallized from ethanol and melted at 143-145 ° C. The invention of the method of producing 10-cyan-5H-dibenz (b), is azepine-5-carboxamide of formula CN, characterized in that the compound of the formula where X is halogen, is treated with ammonia. Sources of information taken into account during the examination 1. Buler K., Pearson D, Organic syntheses. M., World, 1973, p. 388
    类似技术:
    公开号 | 公开日 | 专利标题
    EA018227B1|2013-06-28|A method for the preparation of dabigatran and its intermediates
    SU508205A3|1976-03-25|The method of obtaining derivatives of isoflavone
    EP1138677B1|2003-06-04|Process for the preparation of 11-amino-3-chloro-6,11-dihydro-5,5-dioxo-6-methyl-dibenzo[c,f][1,2]-thiazepine and application to the synthesis of tianeptine
    SU828963A3|1981-05-07|Method of preparing 10-cyano-5h-dibenz-|-azepin-5-carboxyamide
    CN108467353B|2020-09-11|Preparation method of enantiopure tert-butyl sulfinamide
    CN106866480A|2017-06-20|Many cyclophane selenide analog derivatives and preparation method thereof
    CN110903264A|2020-03-24|Method for preparing diazoxide
    CN108409615B|2020-09-11|Method for synthesizing enantiopure tert-butyl sulfenamide
    CH616418A5|1980-03-31|
    EP0018473B1|1982-12-29|Process for the preparation of beta-alkoxy-acrylonitriles, 3-amino-acrylonitriles and 2-cyano-vinyl esters
    FI63750B|1983-04-29|PROCEDURE FOR FRAMSTATION OF AV 2-OXO-PYRROLIDINE-N-ALKYLAMIDER
    US3280120A|1966-10-18|Substituted benzoxazines, process therefor and intermediates
    EP0135304A2|1985-03-27|Preparation of substituted benzamides
    CN106966937A|2017-07-21|Diaryl selenide analog derivative and preparation method thereof
    EP0090203B1|1986-11-12|Process for preparing p.chlorophenoxyacetyl-piperonylpiperazine
    RU2264384C2|2005-11-20|Method for preparing 2- and 4-alkylamino-3-amino-5-nitrobenzoic acids
    FI62531B|1982-09-30|PROCEDURE FOR THERAPEUTIC ADMINISTRATION OF THERAPEUTIC 3-YAN-N- | -IMINOBENSYL OCH SYRAADDIT IOSSALTER DAERAV
    CN107043342A|2017-08-15|Arylalkyl thioethers analog derivative and preparation method thereof
    HU220971B1|2002-07-29|Process for producing 0-|-hidroxim acid halogenids
    US20120232262A1|2012-09-13|Method for preparing n-succinimidyl n-biotinyl-6-aminocaproate
    Isidor et al.1973|Synthesis of 2-methylene-4-thiazolidinones
    JP3640319B2|2005-04-20|Method for producing benzamide derivative
    US2916495A|1959-12-08|Beta-thianaphthenylalkyl hydrazines and intermediates
    Jonas1984|Configuration of sodium salt and preparation of sulphonates and carboxylates of |-and |-3-| dihydro-2 |-furanone
    FI88292C|1993-04-26|FRAME STARTING FOR N- | FORMAMIDER
    同族专利:
    公开号 | 公开日
    NZ192082A|1982-03-16|
    EP0011603A1|1980-05-28|
    AR224137A1|1981-10-30|
    HU178204B|1982-03-28|
    US4235895A|1980-11-25|
    PT70426A|1979-12-01|
    NO793613L|1980-05-13|
    GR74085B|1984-06-06|
    FI793485A|1980-05-11|
    DD146947A5|1981-03-11|
    DK476779A|1980-05-11|
    ZA796042B|1980-10-29|
    AU5262779A|1980-05-15|
    AU525917B2|1982-12-09|
    BG30918A3|1981-09-15|
    ES485812A1|1980-07-01|
    JPS5566561A|1980-05-20|
    IL58679D0|1980-02-29|
    PL219519A1|1980-08-11|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    US2948718A|1960-08-09|New n-heterocyclic compounds |
    DE1136707B|1957-12-20|1962-09-20|Geigy Ag J R|Process for the preparation of N-substituted azepines|
    CH375360A|1959-01-12|1964-02-29|Geigy Ag J R|Process for the preparation of new N-heterocyclic compounds|
    CH605791A5|1974-09-27|1978-10-13|Ciba Geigy Ag|
    US3985730A|1974-11-04|1976-10-12|G. D. Searle & Co.|5-Alkyl-10--10,11-dihydro-5H-dibenz[b,f]azepine-10-alkanamines|FI75561C|1979-10-30|1988-07-11|Ciba Geigy Ag|Process for the preparation of 5-carbamoyl-10-oxo-10,11-dihydro-5H-di benz / b, f / azepine and necessary intermediates thereto.|
    US4431641A|1980-10-17|1984-02-14|Ciba-Geigy Corporation|Pharmaceutical compositions having antiepileptic and antineuralgic action|
    EP0108715A1|1982-10-15|1984-05-16|Ciba-Geigy Ag|Dibenzazepine carboxamides|
    US20060252745A1|2005-05-06|2006-11-09|Almeida Jose L D|Methods of preparing pharmaceutical compositions comprising eslicarbazepine acetate and methods of use|
    GB0700773D0|2007-01-15|2007-02-21|Portela & Ca Sa|Drug therapies|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    CH1158878|1978-11-10|
    [返回顶部]