• 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:
    Es werden neue substituierte ß-Carbotine der allgemeinen Formel worin R3 den 5-Oxadiazolylrest mit R' in der Bedeutung von C1-3-Alkyt und C3-6-Cycloalkyl und den Alkyloxycarbonylrest -COOR" mit R" in der Bedeutung von C1-4-Alkyl, R4 Wasserstoff, Methyl, Ethyl und Methoxymethyl und RA den Arylrest und den Aralkylrest mit X in der Bedeutung von C1-12-Alkyl, wobei der Alkylrest geradkettig, verzweigkettig, gesattigt und ungesättigt und eine CH2-Gruppe durch eine Carbonylgruppe substituiert sein kann, und mit R"' in der Bedeutung von Fluor, Chlor, Brom oder Jod, C1-3-Alkyl, Ci-3-Alkoxy, C1-5-Acyloxy, Phenyl, C2-s-Alkylendioxy, Trifluormethyl, Nitrilo, Nitro oder einer Aminogruppe-NRIVRV mit RIV und RV in der Bedeutung von Wasserstoff, C1-3-Alkyl, C1-5-Acyl und Phenyl, wobei RIV und RV gleich oder verschieden sein können und gemeinsam mit dem Amino-Stickstoffatom ein 3-6-gliedriges Heteroringsystem bilden können, wobei der Substituent R"' einfach oder mehrfach, gleich oder verschieden am Arylrest auftreten kann und Verfahren zu ihrer Herstellung beschrieben. Die erfindungsgemäßen Verbindungen zeigen eine Wirkung auf das Zentralnervensystem und eignen sich somit als Psychopharmaka.
    公开号:SU1376946A3
    申请号:SU843747801
    申请日:1984-06-07
    公开日:1988-02-23
    发明作者:Зайдельман Дитер；Шмихен Ральф；Хут Андреаш；Рац Дитер；Тико Браештруп Клаус；Энгельштофт Могенс
    申请人:Шеринг Аг (Фирма)；
    IPC主号:
    专利说明:

     CM
    The invention relates to a process for the preparation of new derivatives of B-carbolene of the general formula
    where R is C-C-alkyl
    R is hydrogen, methyl, ethyl or
    R -
    methoxymethyl; aryl formula
    or aralkyl formula -X
    (
    25
    R. X is unsubstituted or substituted by a carbonyl group With-C - alkyl;
    the same or different fluorine, chlorine, bromine, iodine, alkyp, C, -C-alkoxy, C, -C j-acyloxy group trifluoromethyl or nitro, 30 1 or 2,
    rye can be used in cava psychotropic drugs in medicine
    P
    The purpose of the invention is the development of cno
    It is possible to obtain new compounds from the class B-carbolines, which would have a higher efficacy in the action on the central nervous system in comparison with structural analogues, for example, ethyl ester of B-carboline-3-carboxylic acid.
    Example 1.0.3 g of 5-hydroxy-4-methoxymethyl-B-carboline-3-carboxylic acid ethyl ester in 60 ml of ethanol with 0.3 g of potassium carbonate and 0.174 g of 3-fluorobenzyl chloride under nitrogen atmosphere are heated under reflux within 4h After filtration and concentration in vacuo, the residue is chromatographed on silica gel (methylene chloride + ethanol 1000 + 25). 0.167 g of 5- (3-fluorobenzyloxy) -4-methoxymethyl-B-carboline-3-carboxylic acid ethyl ester is obtained, m.p. 188 ° C.
    Example 2. Analogously to example 1 from 5-hydroxy-4-methoxymethyl-B-carboline-3-carboxylic ester






    0
    five
    0
    five
    0
    The following compounds are obtained from the acid and the corresponding substituted benzyl halide:
    5 (2-fluorobenzyloxy) -4-methoxymethyl-B-carboline-3-carboxylic acid ethyl ester, m.p. 139-140 ° C, yield 21.3%;
    5- (4-Fluorobenzyloxy) -4-methoxymethyl-B-carboline-3-carboxylic acid ethyl ester, m.p. 174-17b s, yield 23.9%, ethyl yvir 5- (4-chlorobenzyloxy) -4-methoxymethyl-B-carboline-3-carboxylic acid, m.p. 191-193 0,
    5- (3-chlorobenzyloxy) -4-methoxymethyl-B-carboline-3-carboxylic acid ethyl ester, m.p. 196 C, yield 41.2%,
    5- (2-chlorobenzyloxy) -4-methoxymethyl-B-carboline-3-carboxylic acid ethyl ester, m.p. 174-176 C, yield 32% i
    5- (2,5-dichlorobenz1-hydroxy) -4-methoxymethyl-B-carboline-3-carboxylic ester ethyl ester; 191-192 ° C, yield 51.9%;
    5- (3,5-dichlorobenzyloxy) -4-methoxymethyl-y-carboline-3-carboxylic acid ethyl ester, mp, 165-, yield 45.9%;
    ethyl ester of 5- (2,6-dichlorobenzyl-oxy) -4-methoxymethyl-B-carboxyl-3-carboxylic acid, so pl. 209-210 s.
    yield 34.2%;
    ethyl ester of 5- (3,4-dichlorobenyl-oxy) -4-methoxymethyl-B-carbolin-3-carboxylic acid, so pl. 172 C, yield 24% i
    ethyl ester of 5- (3-bromobenzene-1) -4-methoxymethyl-B-carboline-3-carboxylic acid, m.p. 209 ° C, yield 42.7%}
    5- (3-trifluoromethyl-benzyloxy) 4-methoxymethyl-B-carbobin-3-carboxylic acid ethyl ester, m.p. 202 ° C; yield 35.1%;
    5- (4-nitrobenzyloxy) -4-methoxymethyl-B-carboline-3-carboxylic acid ethyl ester, m.p. 186 ° C, yield 26.2% i
    5- (3-methoxybenzyl-oxy) -4-methoxymethyl-B-carboline-3-carboxylic acid ethyl ester, mp. 190 ° C, yield 49.4%;
    5- (2,4-dimethoxybenzyloxy) -4-methoxymethyl-B-carboline-3-carboxylic acid ethyl ester, m.p. 185 ° C, yield 43.5%}
    5- (3,4-ethylenedioxy benzyloxy) -4-methoxymethyl-B-carbolin-3-carboxylic acid ethyl ester, yield
    16.2%;
    5- (3,4-methylenedioxybenzyloxy) -4-methoxymethyl-B-carboline-3-carboxylic acid ETHYL ESTER, m.p., 212 ° C, yield 36.4%,
    5- (4-methylbenzyl-oxy) -4-methoxymethyl-fl-carboline-3-carboxylic acid ethyl ester, m.p. 164 ° C, yield 22.3% j
    5- (3,4-dimethyl-benzyloxy) -4-methoxymethyl-B-carboline-3-carboxylic acid ethyl ester, m.p. , yield 22.9%;
    (3-chlorophenyl) ethoxy-4-methoxymethyl-B-carboline-3-carboxylic acid ethyl ester, m.p. 166 ° C;
    5-G1- (4-chlorophenyl) -ethoxy-4-methoxymethyl-B-carboline-3-carboxylic acid ethyl ester, mp 158 ° C;
    5- (4-chlorophenazsthoxy) -4-methoxymethyl-B-carboline-3-carboxylic acid ethyl ester, m.p. 204-207 ° C,
    Example 3. Analogously to example 1, from 5-hydroxy-4-methyl-B-carboline-3-carboxylic acid ethyl ester and the corresponding substituted benzyl halide, 5- (2-chlorobenzyloxy) -4-methyl-: ethyl ester is obtained -carbo lin-3-carboxylic acid.
    Example 4. Analogously to Example 1, the following compounds are prepared from 5-hydroxy-4-ethyl-B-carboline-3-carboxylic acid ethyl ester and the corresponding substituted benzyl halide:
    5- (3-chlorobenzyloxy) -4-ethyl-B-carboline-3-carboxylic acid ethyl ester, m.p. 137-139 ° C, yield 34.2%
    ethyl ester 5 (2-fluoro-benzyloxy) 4-ethy-1-B-carboline-3-carboxylic acid, m.p. 75-80 ° C, yield 33%.
    Example 5. Analogously to Example 1, 6- (3-chlorobenzyloxy) -B-carboline-3-carboxylic acid ethyl ester is obtained from 6-hydroxy-B-car bolin-3-carboxylic acid ethyl ester and the corresponding substituted benzyl halide, t. square 230-232 ° C, yield 32%.
    Example 6. Analogously to Example 1, the following compounds are prepared from 6-hydroxy-4-methoxy methyl-B-carboline-3-carboxylic acid ethyl ester and the corresponding substituted benethyl halide:
    five
    0
    five
    Q
    ,
    0
    0
    ethyl ester of b- (3- h. türbenzyloxy) - 4-me.toximethyl-B-carboline-3-carboxylic acid, m.p. 185-187 ° C, yield 54.2%;
    6- (3,4-dichlorobenzyl-oxy) -4-methoxymethyl-i-carboline-3-carboxylic acid ethyl ester, mp. 169-170 0, yield 45.3%;
    6- (4-methylbenzyloxy) -4-methoxy-ethyl-B-carboline-3-carboxylic acid ethyl ester, m.p. , yield 35.8%;
    6- (4-nitrobenzyl-oxy) -4-methoxymethyl-B-carboline-3-carboxylic acid ethyl ester, m.p. 156 ° C (decomposition), yield 42%;
    6- (2,5-dichlorobenzyloxy) -4-methoxymethyl-B-carboline-3-carboxylic acid ethyl ester, m.p. 195-198 ° C, yield 17.4%.
    Example 7. In 10 ml of the corresponding alcohol, 100 mg of metallic sodium is dissolved, then 1 g of the obtained ethyl ether derivative is added, the reaction mixture is heated at 60-80 ° C. The reaction time is determined by thin layer chromatography. The reaction mixture is poured into ice-water with stirring and the precipitated product is filtered, washed with water, dried and then recrystallized. The following compounds are prepared analogously:
    5- (2,4-dimethoxy-benzyloxy) -4-methyl-B-carboline-3-carboxylic acid methyl ester;
    5-1- (3-chlorophenyl) ethoxy-4-methoxymethyl-B-carbolin-3-carboxylic acid and propyl ester, m.p. 163-, yield 25%;
    6- (4-chlorobenzyl-oxy) -4-ethyl-B-carboline-3-carboxylic acid methyl ester;
    6- (4-chlorobenzyl oxy) -B-carboline-3-carboxylic acid methyl ester.
    Prev 8. 0.2 g of 4-methoxy-bromobenzene, 0.3 g of ethyl 6-OXY-4-methoxymethyl-B-carboline-3- ester, carboxylic acid and 0.15 g of copper oxide - 1 in 5 ml the collidine is boiled for 35 h. After cooling, it is filtered and concentrated in vacuo. The residue is dissolved in ethyl acetate, extracted several times with cooled ice with 25% ammonia solution and then washed with a saturated solution of sodium chloride, and dried over sulfate.
    513
    calcium and evaporated. By chromatography on silica gel using methylene chloride-ethanol (10: 1), 0.17 g of ethyl 6- (4-labels, xyphenoxy) -4-methoxymethyl-6-carboline-3-carboxylic acid, m.p. 154.0 C.
    The novel compounds (I) exhibit psychotropic effects and are not toxic.
    Certain sites in the vertebrate central nervous system are known to have a high specific agent for binding 1,4- and 1,5-benzodiazepines. Places called benzodiazepine receptors.
    Substituted B-carbolines, although they are strongly chemical in structure

    Groups of drugs are injected at various doses and usually subcutaneously. After 15 minutes, mice were injected intravenously with H-flunitrazepam. After the next 20 minutes, the mice are sacrificed, the shell of their forebrain is removed, and the radioactivity of the membrane of the forebrain is measured using a scintilla counter. The ED5O value is different from the benzodiazepines; neo-2o is calculated using dose / effect curves.
    They have strong affinity and specificity for binding to benzodiazepine receptors in order to displace radioactively labeled flunitrazepam from these benzodiazepine receptors.
    The displacing activity of the new compounds is listed in the table as 1C | 5c, and, where ICjc is the value that indicates the concentration that results, Q is the 50% displacement of the specific bond H-flinitrazepam (1.0 nM) in samples total volume of 0.55 ml of suspension of the brain membrane, for example, rats.
    The displacing activity in the in vitro test is determined as follows: 0.5 ml of a suspension of untreated rat primary brain in 25 mM, pH 7.1 (5-10 mg tissue / sample) is incubated for 40-60 minutes at 0 Together with H-diazepam (specific activity of 14.4 Ci / mmol, 1.9 nM) or H-flunitrazepam (specific activity of 87 Ct / mmol, 1.0 nM). After incubation, the suspension is filtered through a glass frit (glass filter), the residue is washed 2 times with cold buffer solution, and the radioactivity is measured by spindallion35
    40
    45
    50
    wie,
    New compounds in pharmacological test have axiolytic, anti-aggression and anticonvulsant activity. Two types of tests are used to study the anticonvulsant effect: cessation of spasms induced by pentylenatatrazole (pentazole) and cessation of spasms induced by methyl ester 6,7-dimethoxy-4-eth1 1-B-carbolyn-3-carboxylic acid are investigated ( DMSM). Pentazol, respectively, DMSM is administered in the amount of 15 mg / kg as an aqueous solution (pH 7) intraperitoneally, respectively, 150 mg / kg as a hydrochloric acid solution (pH 2-3) after 15-30 minutes after intraperiolysis. - Toneal administration of the test substance. These values induce conical and tonic spasms, which, in the case of untreated animals, lead to death. The number of mice that show spasms, and the number of those that died 30 minutes after the administration of pentazol, respectively, DMSM, is recorded.
    These ED-values were determined by the known method of Litchfield and Wilcoxon (1949) as
    Mr. counter.
    The experiment is then repeated, however, so that before the addition of the radioactively labeled benzodiazepine, a certain amount or an excess amount of the compound is introduced, the displacement activity of which must be determined. Based on the values obtained, the 1C " fo-value is calculated.
    The ED.p value represents
    the dose of the test substance, which causes a decrease in the specific binding of flunitrazepam to the benzodiazepine receptor in the living brain to 50% of the control value.
    The test in vivo is performed in an elec- tive manner.
    Groups of drugs are injected at various doses and usually subcutaneously. After 15 minutes, mice were injected intravenously with H-flunitrazepam. After the next 20 minutes, the mice are sacrificed, the shell of their forebrain is removed, and the radioactivity of the membrane of the forebrain is measured using a scintilla counter. The ED5o value is determined using dose / effect curves.
    Q
    five
    0
    five
    0
    wie,
    New compounds in pharmacological test have axiolytic, anti-aggression and anticonvulsant activity. Two types of tests are used to study the anticonvulsant effect: cessation of spasms induced by pentylenatatrazole (pentazole) and cessation of spasms induced by methyl ester 6,7-dimethoxy-4-eth1 1-B-carboline-3-carboxylic acid ( DMSM). Pentazol, respectively, DMSM is administered in the amount of 15 mg / kg as an aqueous solution (pH 7) intraperitoneally, respectively, 150 mg / kg as a hydrochloric acid solution (pH 2-3) after 15-30 minutes after intraperiolysis. - Toneal administration of the test substance. These values induce conical and tonic spasms, which, in the case of untreated animals, lead to death. The number of mice that show spasms, and the number of those that died 30 minutes after the administration of pentazol, respectively, DMSM, is recorded.
    These ED-values were determined by the known method of Litchfield and Wilcoxon (1949) as
    an antagonistically active substance that protects. 50% of animals from spasm and death.
    The new compounds have a spasm-freeing, respectively, an anti-spasmodic effect in the Andiogenic Seizure test. To do this, male mice aged 18–21 days weighing 8–12 g (TWO) 30 min before test.
    This substance was administered intraperitoneally in the form of an ultrasound microsuspension in a mixture of water and Cremofor REL (95: 5). The animals are then in soundproof wooden boxes (25x22x15 cm) subjected to a 14 kHz sine tone at W (dB). A tone (sound) is created immediately after the animal is converted to a box. The occurrence of climatic convulsions is recorded for 30 s. The Eudud value is presented in the table in which the dose of 40% for men with a W (80% of the smaller ones show spasms with a W) does not show any spasms.
    The pharmacological properties of R-substituted ethyl esters of 5-benzyloxy-4-methoxymethyl-B-carboline-3-carboxylic acid are listed in the table.
    As follows from the data in the table, the novel compounds (I) exhibit a more effective psychotropic effect than the known one.
    or aralkyl of the general formula
    - (iln
    where X is unsubstituted or substituted by a carbonyl group With, -C, -alkyl R. is the same or different,
    fluorine, chlorine, bromine, iodine, C, -a, -alkyl, C — C-alkoxyl, C.j-Cj atshoxy group ,. trifluoromethyl or nitro, p 1 or 2,
    Recalling the fact that hydroxy-carboline of the general formula
    COORi
    -TO
    权利要求:
    Claims (1)
    [1]
    Invention Formula
    The method of obtaining 6-carboline derivatives of the general formula
    jCOORi
    R
     - C-C-alkyl; hydrogen, methyl,
    2ethyl or
    methoxymethyl;
     general formula
    (R / tlh
    25 where R and RJ are the indicated values,
    subjected to interaction with the compound of the General formula
    R, Y,
    where RJ is as defined, Y is chlorine or bromine,
    in ethanol and in the presence of base
    I
    during boiling followed by the selection of the target product or its re-esterification with the corresponding alcohol of the general formula
    R, OH, where R, is as defined.
    13769А6 О
     Table continuation
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