• 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:
    Chemical compounds of the formula <IMAGE> wherein B, R1, R2, R3, R7, R8, m and n are as defined hereinbelow, which compounds are intermediates for the preparation of antiemetic agents.
    公开号:SU795466A3
    申请号:SU772532654
    申请日:1977-10-17
    公开日:1981-01-07
    发明作者:Ванденберк Жан；Е.Ж.Кеннис Людо；Ж.М.С. Ван Дер Аа Марсель；Н.М.Ч.Ван Эртум Альберт
    申请人:Жансен Фармасетика Н.В. (Фирма)；
    IPC主号:
    专利说明:

    (54) METHOD. PREPARATION OF DERIVATIVES 1- (BENZAZOLILALKIL) PIPERIDINE OR THEIR SALTS
    higher value with qi
    gento CS or NA or
    About N 11 /
    QN-C-N J
    with the subsequent allocation of the target product in free form or in the form of salt.
    Compounds obtained by the present method can be used to suppress vomiting in warm-blooded animals by systemically administering an effective antiserum amount of a compound of general formula I and their pharmaceutically acceptable acid addition salts in combination with pharmaceutical and pharmaceutical carriers.
    This invention is illustrated by the following examples, confirming | .1 but not limiting the present invention. Parts indicating the amount of reagent is by weight.
    Example 1. A mixture of nz 38 parts of carbon disulfide, 6 parts of (3-W (2-aminophenyl) aminopropyl) -4-piperidine-5-chloro-1, 3-dihydro-2H-benzimidazol-2-one and 32 parts of ethanol are mixed and The mixture is boiled under reflux for 24 hours, after which the mixture is evaporated and the residue is crystallized from ethanol. Then pro / v
    CH2-N; J with
    W
    A, H II
    - C, i3- “n, -“ O (xC.
    m
    to a stirred mixture of 5.2 parts A, 90 parts C, a solution consisting of 4 parts B in 45 parts C is added. BcUOT is first mixed quickly at room temperature and then at room temperature for 5 h. The interacting mixture is evaporated and the residue is placed in water. The precipitated product is filtered, taken up in water and dissolved in trichloromethane. The solution is dried, filtered and evaporated, the residue is taken up in hydrochloride salt in 2-propanol. After filtration and drying, 2 parts (31%) of the desired product D are obtained; mp. 243,
    A: 1- (1- 3 - ((2-amino-4-fluorophenyl) -amino) propyl-4-piperidinyl) -5-fluoro-1, 3-dihydro-2H-benzimidazole-2-OH.
    The product is filtered and recrystallized for the second time from a mixture of L, L-dimethylformamide and water. Get 3 parts. (45.5%) 5-chloro-1- (1- (3-C2,3-dihydro-3-thioxy-1H-benzimidazol-1-yl) propyl) -4-piperidinyl} -1.3. dihydro-2H-benzimidazol-2-one with so pl. 266.6 ° C.
    Example 2. A mixture of 4 parts of 1- (1 (3-N- (2-amino-5-chlorophenyl) -amo) propyl-4-piperidinyl) -1,3-dihydro-2H-benzimidazol-2-one , 6 Parts of a solution of concentrated hydrochloric acid and 30 parts of formic acid are stirred and refluxed overnight,
     whereupon the mixture is evaporated and water is added to the residue. The whole mixture is made alkaline with a solution of dilute ammonium hydroxide and the product is extracted with chloroform, then the extract
    0 is dried, filtered, evaporated and the residue is crystallized from 4-methyl-2-pentanone, filtered and recrystallized from 2-propanol. 1.1 parts (27%) of 1- {1- (3- (6-chloro-1H-benzimidazol-1-yl) propyl) -4-piperidinyl-, 3-dihydro-2H-benzimidazol-2-one are obtained m.p. 219.9 s.
    Example 3. 1- (1 - {- 3- (2-amino-4-fluorophenyl) -amino) propyl-4-piQ peridinyl) -5-fluoro-1,3-DIGIDRO-2H-benzimidazole-2- HE .
     R
    . g
    B: 1, (1H-imidazol-1-yl) methanone.
    With tetrahydrofuran.
    D: 5-fluoro-1 -3- (4- (5-fluoro 2,3-dihydro-2-oxo-1H-benzimidazol-1-yl) propyl, 3-dihydro-2H-benzimidazole-2-OH-monohydrochloride -2-propanolate (2: 1). Example 4. A mixture of 20 parts of 1- ((2-amino-4-chlorophenyl) amino) -1-piperidinyl1propyl) -1,3-dihydro-2H-benzimidazol-2-one , 52 parts of carbon disulfide and 120 parts of ethanol are stirred and refluxed for 24 hours, then cooled and filtered, the filtrate is evaporated and the residue is crystallized from 2-propanol. The product is filtered and recrystallized again from ethanol.
    after drying, 7.5 parts (34%) of 1-h- (4- (5-chloro-2,3-dihydro-2-thioxo-1H-ben-imidazol-1-yl) -l-piperidinyl) propyl g-l are obtained 3-dihydro-2H-benimide-2-one with so pl. 254.3 ° C.
    Example 5. In analogy to Example 4, 1- (3- {4 - ((2-aminophenyl) amino) -1-piperidinyl propyl) -1,3-dihydro-2H-benzimidazol-2-one with carbon disulfide is obtained by reacting carbon disulfide (4- (2,3-Dihydro-2-thioxo-1H-benzimidazol-1-yl) -1-piperidinyl) propyl -1, 3-dihydro-2n-benzimidazol-2-one with so pl. 248.5 ° C.
    权利要求:
    Claims (1)
    [1]
    1. Weigand Hilgetag. Experimental methods in organic chemistry, M., Himi, 1968, p. 379.
    类似技术:
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    US4110333A|1978-08-29|
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    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    CA928296A|1967-06-05|1973-06-12|Umio Suminori|N-substituted and n, n-disubstituted aminocarbonylalkyl compounds and their production|
    US3635982A|1969-04-08|1972-01-18|American Home Prod|Amino-substituted-quinoxalinyloxazolidines and -oxazines|
    GB1304599A|1969-07-16|1973-01-24|
    JPS5755714B2|1972-03-18|1982-11-25|
    US3951978A|1972-04-22|1976-04-20|Istituto Luso Farmaco D'italia S.R.L.|1,3-Disubstituted 3-aroylpropanes and process for the preparation thereof|
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    US5039528A|1989-12-11|1991-08-13|Olney John W|EAA antagonists as anti-emetic drugs|
    DK0533280T4|1991-09-20|2005-02-28|Glaxo Group Ltd|New medical use of tachykinin antagonists|
    FR2725986B1|1994-10-21|1996-11-29|Adir|NOVEL PIPERIDINE DERIVATIVES, THEIR PREPARATION PROCESS AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM|
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    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    US05/687,139|US4066772A|1975-07-21|1976-05-17|1,3-Dihydro-1-[3-propyl]-2H-benzimidazol-2-ones and related compounds|
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