• 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:
    1417461 Tetrazolyl chromone derivatives TAKEDA YAKUHIN KOGYO KK 12 April 1973 [12 April 1972] 17602/73 Heading C2C The invention comprises compounds having the general formula wherein m is 0, 1 or- 2; n is 0 or 1; and each R, which may be the same or different, is halogen, nitro, hydroxy, alkyl, alkoxy, acyloxy, carboxy, carboxamide or amino, or two R groups on any two adjacent carbon atoms at positions 5, 6, 7 or 8 together form a benzene ring; or pharmaceutically acceptable salts thereof. They may be prepared by reacting hydrazoic acid or a salt thereof with a compound of the general formula The compounds of the invention exhibit antiallergic activity and may be administered orally or parenterally alone or in admixture with a suitable diluent or carrier.
    公开号:SU745367A3
    申请号:SU752099318
    申请日:1975-01-17
    公开日:1980-06-30
    发明作者:Нохара Акира；Уметани Томонобу；Санно Ясуси
    申请人:Такеда Кемикал Индастриз Лтд (Фирма)；
    IPC主号:
    专利说明:

    The solvent preferably used is hydrocarbons, eg, benzene, petroleum ether; as well as ethers, such as methyl ether, ethyl ether, such alcohols, kick methanol, ethanol. Preferred base is tert-amine, for example, trimethylamine, triethylamine, K-methylpyridine, N-methylmorpholine, N-methylpyr rolizine, pyridine, 2-methylpyridine, 3-methyl-pyridine, quinoline, 2-methylquinoline, imidaeol , 2-methylimidazole, etc. These bases can also serve as a solvent in the reaction. The reaction conditions, including the reaction temperature and reaction time, are dependent on the type of solvent and the starting compound. Preferably, the process is conducted at a temperature from room temperature to the boiling point of the reaction medium, xbt, if desired, the reaction can be carried out (Lead at a reduced temperature. Duration of the process is allowed to remain from several minutes to 10 hours. Interaction with Hydroxydromine is preferred carried out at a temperature of 0-150 0. Example 1. 2.52 parts of 4-6 x -4H-1-benzpyran-3-carboxaldehyde are mixed with 2.10 parts of chloro-hydroxylamine and then 30 parts by volume are added. % of alcohol and 0.5 parts by volume of concentrated concentrated acid. The whole mixture is heated with cool with a cooler and cool. The precipitate formed is separated by filtration, treated with activated carbon and recrystallized from ethanol to give 4-oxo-4H-1-benzpyran-3-carbonitrile in the form of colorless crystals; mp. 177-178c. C pHgNO .. Calculated,% "C 70.17; H 2.95 N 8.19. Found,% C 70.00; H 2.80; N 8.13. Example 2. Mixture 10.44 h. 4 -oxo-4H-1-benzpyran-3-carboxaldehyde and 5,4-h / cyanoacetic acid are heated from an oil bath at 110 ° C and a mixture of 25 parts by volume is added dropwise to the mixture. pyridine for 30 seconds (yosle) the mixture is also heated for 8 minutes. After cooling, the precipitated crystals are filtered, treated with activated carbon and yorekrystallis three times from ethanol. You get a trans-3- (4-OKso-4N-1-benzpyran-3-yl) -acrylonitrile in the form of light yellow prisms; m.p. 192-194 ° C. , Calculated% C 73.09; H 3.58; N 7.10. Found: C: 73.49; H, 3.60; N, 7.01. For the same method, the compounds shown in the table are obtained.
    6-Methyl-4-oxo-4 6-Methyl-4-oxo-4H-1-benepirin-3-1-benzpyran-3-car-carbonitrile box aldehyde 6-ETHIL-4-OXO-4N 6-ETHIL-4- OXO-4N-1-benepiran-Z-1-5benzpiran-3-carboxalDegide -carbonitrile b-Chloro-4-oxo-4Nb-Chloro-4-oxo-4N -1-benzpyran-3-car-1-benzpyrane Zboxaldehyde - carbbyte yl b-MetOxY-4-oxo 6-Methoxy-4-oxo-4H-4H-1-benzpyran-1-benzpyrane-Z.-3-carbonitrile-carboxyLdehyde 6-n-Hexyl-4-oxobn n Hexyl -4-6k-4N-1-benzpyran-3c6-4H-1-benzpirai-3-carbonitri-carboxaldehyde 7-n-Butoxy-4-oxo6-n-Butoxy-4-ok-4N-1-benzya ran-3с -4H-1-ben9pyra -3-carbonitrile-carboxaldehyde
    b-Dimethylamine-4-OXO-4N-1-bvnzpiran-3-carbonitrile
    Yellow needles of chlo- 167-168 roform + ethyl acetate. Colorless needles 152.5-153.5 (ethanol) 123-124. Colorless crystals (ethanol) 210-213. Yellow prisms (methanol) Exits nyyu and gly 194-195 (ethanol) 55 ki colorless plates (ethanol-hexane) Light yellow 120-121 plates (benzal + + m-hexane) 3-Formyl ben 3 ohromon
    3-1Dianbenzohromon Colorless needles
    3-Formyl ben3 ohromone b-Cyclohexyl-46-Cyclohexnl-4-oxo-4H-1-benz-oxo-4H-1-benzpi-pyran-3-carbonite ran-3-carboxaldaryl 6-n-propyl-4- ox b-n-propyl-4-oxo-4N-1-benzpyran-4N-1-benzpyran-3-carbonitrile-3-carboxaldehyde 6-isopropyl-4-oxo-6-isopropyl-4-ok-4H-1-benzpir -4H-1-benzpyran-3-3-carbonyl-carboxaldehyde 7-methoxy-4-oxo 7-methoxy-4-oxo-4H-1-benzpcran-4H-1-benzpyrane-3-3-carbonitrile-carboxaldehyde b- n-Butyl-4-oxo bn n-Butyl-4-oxo-4n-1-benzpyran-3-4H-1-benzpyran-3-carbonitrile-carboxalide guide trans-3- (bn-Bu6-n- Butyl-4-oxotil-4-oxo-4N-1-4N-1-benzpyran-3-ben zpiran-3-yl) -carboxaldehyde-acrylonitrile 6-Nitro-4-oxo-4 6-Nitro-4-rxo-4H-1-benzpyran-3-1-benzpyran-Z-car-carbonitrile box aldehyde 7-Acetoxy-4 -oxo7-OXI-4-OXO-4N -1-benzpyran-3-4N-1-benzpyran-3-carboxaldehyde -carbonitrile b-Ethoxycarbenyl 6-Ethoxycarbonyl-4-oxo-4N-1-ben-4-oxo-4N -1-benzpyran-3-carbonite pyran-3-carboxalryl dehyd b, 8-dimethyl-4-ca 6.8-dimethyl-4-oxo-4H-1-benzpyran-4H-1-benzpyrane-3-carboxaldehyde-carbonitrile 7-Acetoxy-4-oxo7-Acetoxy-4-ox4H-1-benzpyran-3co-4H-1-benzpi-carboxaldehyde wound-3-carbonitrile 7-Benzoyloxy-4-ok7-Benzoyloxy-4CO-4N -1-benzpyran-oxo-4H-1-be113p-3-carboxaldehyde wound-3-carbonitrile b, 7-DIOXI-4-OXOB, 7-DIOXI-4-OXO-4N-1-b-benzpyran-3-4H-1 -benzpyran-carboxaldehyde -carbonitrile 2-hydroxy-5-chloraceb-chloro-4-oxo-4N-tofenon-dimethylforma-1-benzpyran-zamid
    Table continuation
    194.5-195, -5
    (ethanol) Z-Cyanbenzokh omon: Light brown 229-230 plates (acetone) wind brown 164-165 plates. (methanol) wind yellow needles 102-104 (ethanol) Light yellow needles 118-120 (ethanol) wind - yellow needles 191-193 (methanol) Colorless needles 94-9-5 (ethanol) Colorless needles 124-126 (ligroin + benzene) Colorless plates 211-213 (meth anol + chloroform) Colorless needles (ethanol) 278-280 164- 165 Colorless needles (benzene) 196-198 Colorless 13 needles (acetone) uncolored hair- 182-183 rael-like crystals (ethanol) plates (ethanol- 200-202 tetrahydrofuran) brown-brown 300 orcshoke (dimethyl ormamide-water) ate ches (he166-168)
    权利要求:
    Claims (4)
    [1]
    The claims are distinguished by the unity of the formula with i that
    1. The method of obtaining derivatives of chromon of the formula j and where η is an integer equal to 0 or 1; m is an integer, 0.1 or 2, when R is a hydrogen or Halogen atom, a nitro group, an oxy group, a straight or branched chain alkyl with 1-6 carbon atoms, a cyclic alkyl with 3-6 carbon atoms, or butadiene, which forms a benzene ring with any two adjacent carbon atoms located in positions 5,6,7 and 8, the group COOR 4 , where R 1 * - 50. alkyl with 1-3 carbon atoms, or an amino group unsubstituted or substituted by alkyl with 1-3 carbon atoms, or the group R J COO, where R 3 is alkyl with 1-3 carbon atoms or phenyl, and m is an integer equal to 2, when R is an alkyl with 1-3 carbon atoms, an ok 'sigruzza or a halogen atom, t
    where R »» values are reacted with hydroxy (xylamine or its hydrochloride in an organic solvent such as ethanol) or with cyanoacetic acid in the presence of a base.
    [2]
    2. The method according to claim 1, characterized in that the process of interaction of the compounds of formula L with hydroxylamine is carried out at 0-150 ° C.
    [3]
    3. The method according to claim 1, characterized in that a tertiary amine, such as pyridine, is used as the base.
    [4]
    4. The method according to claim 1, characterized in that the reaction with cyanacetic acid is carried out in an environment of an organic solvent, such as ethanol.
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    引用文献:
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    US4033845A|1975-11-20|1977-07-05|Warner-Lambert Company|[2-ethenyl]benzonitriles and benzoic acids|
    GB1560489A|1976-05-21|1980-02-06|Fisons Ltd|Pharmaceutical compositions|
    US4183946A|1976-06-16|1980-01-15|Carlo Erba S.P.A.|Substituted 2-vinyl-chromones and process for their preparation|
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    US4177276A|1976-06-16|1979-12-04|Farmitalia Carlo Erba, S.P.A.|Substituted 2-vinyl-chromones and process for their preparation|
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    AU508350B2|1976-06-16|1980-03-20|Farmitalia Carlo Erba S.P.A.|Substicuted 2-vinyl-chromones|
    US4116971A|1977-08-15|1978-09-26|Warner-Lambert Company|3-chromones|
    US4360527A|1977-10-13|1982-11-23|Warner-Lambert Company|9--2-naphtho--pyran-1-ones and anti-allergic use thereof|
    DE2840936C2|1978-09-20|1983-02-10|Warner-Lambert Co., 07950 Morris Plains, N.J.|3--chromones and their uses|
    AT14579T|1979-03-20|1985-08-15|Fisons Plc|PHARMACEUTICAL HETEROCYCLIC COMPOUNDS, METHOD FOR THE PRODUCTION THEREOF AND COMPOSITIONS CONTAINING THE SAME.|
    ZA804788B|1979-10-26|1981-07-29|Erba Farmitalia|Substituted 2--chromones and process for their preparation|
    JP2004323392A|2003-04-23|2004-11-18|Toyo Kasei Kogyo Co Ltd|Method for producing bitetrazolamine compound|
    GB201506572D0|2015-04-17|2015-06-03|Johnson Matthey Davy Technologies Ltd|Process|
    法律状态:
    优先权:
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