• 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:SU751324A3
    申请号:SU782674601
    申请日:1978-10-17
    公开日:1980-07-23
    发明作者:Венсан Мишель；Ремон Жорж；Лоби Мишель
    申请人:Сьянс Юньон Э Ко (Фирма)；Сосьете Франсэз Де Решерш Медикаль (Фирма)；
    IPC主号:
    专利说明:

    Union of Soviet
    Socialist
    Republics
    USSR State Committee for Inventions and Discoveries
    DESCRIPTION
    Inventions
    TO PATENT (61) Supplementary to patent ~ (22) Pending 10.17.78 (21) 2502597 / / 2674601 / 23-04 (23) Priority 14.07.77 (32) 14.07.76 (31) 29317 (33) United Kingdom
    Published on July 23, 1980. Bulletin No. 27
    Date of publication of the description 25.0 7.80 (^ 751324
    (51) M. K. 3 from 07 D 401/04 from 07 D 239/907 / A 61 TO 31/495
    (53) UDC 547.856.
    .07 (088.8)
    (72) Authors Foreigners inventions Michelle Vincent, Georges Remon and Michelle Loby(France)
    Foreign company (71) Applicant Syans Union e Co, Societe Francoise de Resherche Medical (France) (54) METHOD FOR PRODUCING 4-CHINAZOLINYL-N-ARALKILPIPERIDINES
    A method for producing new quinazolinone derivatives that can be used as medicaments is proposed.
    The interaction of aralkyl halides with amines is known [lj.
    The purpose of the invention is the development on the basis of the known method of a method for producing new compounds with valuable pharmacological properties.
    This goal is achieved by the method of obtaining 4-quinazolinyl-I-aralkylpiperidines of the General formula
    O (CH 2 ) 2 —X — Ar,
    N where R is hydrogen or chlorine;
    X is oxygen or a direct carbon-carbon bond;
    Ag is indolyl, 4-oxoquinazolinyl, or free or substituted phenyl, wherein N-benzylpiperidine is of the general formula
    where R has the indicated meanings, is subjected to debenzylation by catalytic hydrogenation, the resulting piperidine of General formula
    where Ar, X
    Ζ and target
    At)
    Ιθ where R has the indicated meanings, is reacted with a compound of the general formula
    X - R - Z, and R have the indicated values ·, - a halogen atom or an ester residue, the products are isolated, ί er 1. 1- [2- (Indolyl 20 -3) ethylZ-4- (oxo- [Zn ] -quinazolinyl-3) piperidine.
    A. 3- (Piperidinyl-4) - [3H] -4-oxoquinazoline.
    4-Benzylamino-1- (o-aminobenzoyl) 20 piperidine is debenzylated by catalytic hydrogenation in the presence of palladium to give 4-amino-1- (o-aminobenzoyl) pyridium, which is cyclized. In 3- (pi 30 peridyl-4) -4-oxo ~ [ZN] -quinazoline by heating in formic acid. 3- (Piperidin-4) -4-oxo- [3N] -quinaeoline is purified by recrystallization from acetonitrile.
    Found,%: C 68.10; H, 6.70; N, 17.90.
    ε ^ 65 "3 ° ·
    Calculated,%: C 68.10; H 6.59;
    N, 18.32.
    B. 1- [2- (Indolyl-3) ethyl] -4- (4-oxo-zn] quinazolinyl-3) piperidine.
    11.46 g of 3-piperidinyl-4- [3N] -4-oxoquinazoline obtained in stage A dissolved in 175 ml of methyl isobutyl ketone and 11.66 g of dry carbonate are charged into a three-necked flask equipped with a nitrogen passing tube and a mechanical stirrer. potassium. Then, with vigorous stirring, 24.53 was added dropwise to the suspension. g of bromide. (indolyl-3) ethyl. The mixture was boiled for 12 hours, cooled to room temperature, the precipitate formed was filtered off, washed with several milliliters of methyl isobutyl ketone and added to the filtrate. The filtrate was evaporated to dryness under reduced pressure. Yield 28.65 g. Purification of the target product is carried out by recrystallization from methanol and washing the crystals with ice-cold methanol. The resulting crystals are dried in vacuum, so pl. 189-190 ° C. The target product is soluble in a dilute aqueous solution of methanesulfonic acid.
    Found,%: C
    N, 14.98.
    ^ 23 ^ 24 ^ 4 θ '
    Calculated,%: N 15.04.
    Example of tilphenoxy) ethyl] | -4- (b-chloro-4-oxo-
    - [ZN] -quinazolinyl-3) piperidine.
    Analogously to example 1, starting from 4- (6-chloro-4-oxoquinazolinyl-3) piperidine and 17.70 g of 2- (2,6-dimethylphenoxy) ethyl bromide, upon boiling in methyl ethyl ketone, the desired product is obtained in 63% yield, which recrystallized from isopropanol, so pl. 113-114 ° C.
    Found,%: C 66.93; H 6.58, '
    N, 10.10; Ct 8.35. e 21 H 2b efN 3 ° 2 · Calculated,%: C 67.07; H 6.36;
    N 10/20; CE 8.61.
    Example 3. 1- £ 2- (4-Oxo-
    - [ZN] -quinazolin-3-yl) ethyl] -4- (4-oxo-СЗН] -quinazolin-3-yl) piperidine.
    Editor O. Kuznetsova
    74.07, - Η 6.45;
    s 74.16; n 6.50;
    2. 1— £ 2— (2,6-Dime—
    Similarly to that described in example 1, starting from 11 g of 3- (piperidyl-4) - -4-oxo- З ZH] -quinazoline and 12.4 g of bromide 2- (4-oxo- [3N] -quinazolin-3-yl ) ethyl, get the target product with a yield of 47%. This compound is soluble in dilute hydrochloric acid solutions.
    权利要求:
    Claims (1)
    [1]
    Claim
    The method of obtaining 4-quinazolinyl-N-aralkylpiperidines of the General formula
    Ν 'where is hydrogen or chlorine;
    - oxygen or a direct carbon-carbon bond;
    - indolyl, 4-oxoquinazolinyl or free or substituted phenyl, characterized in that
    Ar about t
    N-beneylpiperidine of the general formula
    N-CH 2 C 6 H5, where R has the indicated meanings, is subjected to debenzylation by catalytic hydrogenation, the resulting piperidine of the general formula where R has the indicated meanings, is reacted with a compound of the general formula
    Ar-X-R-Z, where R, X and Ar have the indicated meanings;
    L is a halogen atom, and the target products are isolated.
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    同族专利:
    公开号 | 公开日
    DE2731299A1|1978-01-19|
    FR2361385B1|1983-10-07|
    ES460699A1|1978-12-01|
    ES472563A1|1979-10-16|
    US4166117A|1979-08-28|
    CH625518A5|1981-09-30|
    CA1103671A|1981-06-23|
    JPS5334784A|1978-03-31|
    NL7707785A|1978-01-17|
    GB1583753A|1981-02-04|
    FR2361385A1|1978-03-10|
    OA05707A|1981-05-31|
    BE856784A|1978-01-13|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    US2694711A|1952-12-02|1954-11-16|American Cyanamid Co|Quinazolone antimalarial compounds|
    US3086910A|1960-03-09|1963-04-23|Wallace & Tiernan Inc|Central nervous system depressants 3--4-quinazolones|
    US3257397A|1963-07-26|1966-06-21|Rexall Drug Chemical|Substituted 2, 3-dihydro-4-quinazolinones|
    US4027028A|1975-11-10|1977-05-31|Science Union Et Cie|Arylethers and pharmaceutical compositions|EP0029707B1|1979-11-21|1984-02-01|Kyowa Hakko Kogyo Co., Ltd|Novel piperidine derivatives, method for the preparation thereof and pharmaceutical compositions containing them|
    US4344945A|1980-03-10|1982-08-17|Kyowa Hakko Kogyo Co., Ltd.|Piperidine derivatives|
    US4684654A|1985-08-14|1987-08-04|American Cyanamid Company|3-heteroalkyl-2,4-quinzaolinediones|
    PH23565A|1986-09-05|1989-08-25|Sumitomo Chemical Co|Novel pyrimidinylpyrimidine derivatives and a plant disease protectant containing them as the active ingredient|
    FI95572C|1987-06-22|1996-02-26|Eisai Co Ltd|Process for the preparation of a medicament useful as a piperidine derivative or its pharmaceutical salt|
    EP0638567A4|1993-02-18|1995-05-10|Kyowa Hakko Kogyo Kk|Adenosine incorporation inhibitor.|
    JP2959765B2|1997-12-12|1999-10-06|日本たばこ産業株式会社|3-piperidyl-4-oxoquinazoline derivative and pharmaceutical composition containing the same|
    US6258819B1|1999-08-05|2001-07-10|SyntexLlc|Substituted 2-4-quinazolinones and 2--4-azaquinazolinones|
    CA2555824C|2004-02-13|2011-06-07|Banyu Pharmaceutical Co., Ltd.|Fused-ring 4-oxopyrimidine derivative|
    AR065081A1|2007-01-29|2009-05-13|Xenon Pharmaceuticals Inc|FUSIONATED QUINAZOLINONA AND PIRIMIDONA COMPOUNDS AND PHARMACEUTICAL COMPOSITION|
    US9040533B2|2012-12-27|2015-05-26|Purdue Pharma L.P.|Oxime-substituted-quinoxaline-type piperidine compounds as ORL-1 modulators|
    JO3512B1|2014-03-26|2020-07-05|Astex Therapeutics Ltd|Quinoxaline derivatives useful as fgfr kinase modulators|
    LT3353177T|2015-09-23|2020-08-25|Janssen Pharmaceutica Nv|Tricyclic heterocycles for the treatment of cancer|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    GB29317/76A|GB1583753A|1976-07-14|1976-07-14|Piperidine derivatives processes for their preparation and pharmaceutical compositions containing them|
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