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    • 专利摘要:
    The invention relates to amine derivatives, in particular, to the derivatives of 3-feNyl-2-propenamine (PAM) of a common f-ly: R-C6H4-CZ CR ,, R ,, where Z-Y-A; R-H, halogen, C, -C "is apyl or apkoxyl; R, -H or CH ;; RJ and RJ (identical or different) -H, C, -C-alknp (it may be substituted by Cj-Cz-alkenyl) or R, RjN together - 1-pyrrol idinyl 9 piperidine; A-C, -C alkyl or phenyl (it may be substituted with halogen or C) -C4-alkyl or pyridyl, benzyl, C, -C-11 Iklos-1 Kyl; Y is sulfur, -OR5; R, - H or Rj - H or acetyl. PAM is obtained in the form of geometric dimensions or their mixtures or pharmacologically acceptable salts exhibiting antidepressant properties. The goal is to create new, more active substances of the specified class. Synthesis of PAM is carried out by the reaction of the corresponding amine with a phenylbutane derivative of the general formulas JI and 111: NHR, R2 (s) and R - CR, -CHjX. (iIt), where R; R, -Rj - see above; a) X is chlorine when Y is sulfur.-OR5 with H or CH and Ry is acetyl; 6} X is bromine when Y is sulfur, and the compound of the f-ly tI1 is in the form of an E or Z configuration. The process is conducted in ethanol or methanol at room temperature. Further, if necessary, the obtained product is hydrolyzed to obtain a compound in which Y is H, and the others are indicated above. The pellet product is isolated or converted to the desired salt. New substances exhibit activity at a dose of 1-21 mg / kg with an LD5 toxicity of 100-300 mg / kg. 1 tab. CO with ND SP
    公开号:SU1402251A3
    申请号:SU864027084
    申请日:1986-03-14
    公开日:1988-06-07
    发明作者:Баррьер Жан-Клод；Корбэ Жан-Пьер；Котрель Клод；Фарж Даниель；Пари Жан-Марк
    申请人:Рон-Пуленк Санте (Фирма)；
    IPC主号:
    专利说明:

     CM
    Otios invention: it to the method of obtaining new derivatives of 3-phenyl--2-propenamine of the general formula
    f5
    Sh
    de R is hydrogen or halogen, or C.C. alkyl or alkoxy; R, is hydrogen or methyl; , and the same or different and hydrogen or C -C-SLC-kil, which can be forgotten. The methyl C-C lkenyl, or R, and R, together with the nitrogen to which they are bound, form a 1-pyrrolidinyl or pi-20 peridin radical; A is C, -C-akyl or phenyl, unsubstituted or substituted by a halogen atom or C, -C 4 alkyl, or A is pyridine, benzyl or cycloalkyl; Y is sulfur or a radical of the formula.
    25
     R
    t
    OTRi
    (Ii)
    where R is hydrogen or methyl; R 5 is hydrogen or acetyl.
    The compounds of formula (I) are obtained as geometric isomers or mixtures thereof, as well as pharmacologically acceptable salts.
    The compounds of forgula (I) have antidepressant properties.
    The aim of the invention is to produce new derivatives in the range of 2 propenamine, which have a higher antidepressant activity.
    Example 1.K 150 cm 4.2 n,
    ammonia ethanol solution, cooled to O C, a solution of 17.2 g of 3-chloro-1-phenyl-I-phenylthio-1-propene (Z) in 68 cm of ethanol was added dropwise. After stirring for 14 hours at room temperature, the reaction mixture is piped dry under reduced pressure (2–7 kPa) at. In this way, a pale yellow paste is obtained, which is processed by 100 cm of Sfr-tnaneTara. The white solid that forms is separated by filtration and recrystallized from 250 cm of methyl ethyl ketone. So
    five
    0
    five
    0
    d
    Q
    five
    0
    five
    o6pa: ioM 1yulyin1t 3,5 i mixture: 75% 3-amiipi-phenyl-1-phenyl-thio-1-propene hydrochloride (Z) H 25% 3-amino-I-phenyl-1-phenylthio-1 chlorohydrate Progreen (E) as a white solid melting at 184 C.
    3-} Lnop-phenyl-1-phenylthio-1 -propylene (Z) can be obtained as follows. To 17.6 g of a dimethyl--1-amine-3-phenyl-3-phenylthio-2-propene (Z) solution in 230 cm of toluene was added 9.4 cm of ethyl chloroforiate. The mixture is heated to 90 ° C. for 2 h 30 min, then evaporated to dryness under reduced pressure (2.7 kPL) at. Thus, 21.8 g of a pale yellow oil are obtained, containing the desired 3-chloro-1-phenyl-1-phenylthio-1-propene (Z) mixed with dimethylethyl carbamate formed during the reaction. This oil is used without further purification in subsequent syntheses.
    Nuclear Magnetic Resonance Spectrum (60 million Hz, CDClj), h. Mln: 4.5, 2H: 6.5, H: -SP-, 6.9-7.5, YN: aromatic.
    Example 2. To a solution of 9.5 g of 4-chloro-1-ethoxycarbonyloxy-1- (3- -fluorophenyl) -2-phenyl-2-butene (Z) in 50 cm of ethanol was added 100 cm of ethanol, 33% - solution of methylamine. After stirring for 2 hours in a dark place, the reaction mixture is evaporated to dryness under reduced pressure (2.7 kPa) at 30 ° C to obtain an oil. This oil is dissolved in 50 cm of distilled water, and the resulting solution is alkalinized to pH 11 by adding 4 n. sodium hydroxide solution, then extracted 3 times with 100 cm of distil ether. The organic phases are combined, dried over magnesium sulphate, filtered, the mixture is evaporated to dryness under reduced pressure (2.7 kPa) at 30 ° C to obtain an orange oil. This oil is dissolved in 40 cm of ethyl acetate, after which 5 cm of a 5.7K solution of hydrogen chloride gas in diethyl ether are added. The solid formed is separated by filtration, then recrystallized from 20 cm of acetonitrile. Thus, 3 g of j- (3-fluorophenyl) -4-methlamine-2-phenyl-2-butene-1-ol (Z) hydrochloride is obtained in the form of a white solid; melt shchegos. at (, 1 ° С,
      1402251 A-Chloro-1-ethoxycarbonyloxy-1- (3- -fluorophenig) -2 phenyl-2-butene (Z) can be semi-en ... as follows. To 26.2 g of a solution of 1-dimethylamine-4-etho-, g sicarboxy-oxy-4-- (3-fluorophenyl) -3-phenyl-2-butene (Z) in 200 cm of toluene was added 10.6 cm of ethyl chloroformate .
    ole slowly at f) (, ds C 1 C 11 and 1 C) t 45 g H-ch.chor-1-phenyl-1-phenyl-1-propium (Z) as a solution in 40 cm of ethanol and continue to flow through for 14 h at room temperature (22 ° C. The reaction mixture is fed under reduced pressure (2.7 kPa) at 30 ° C. The residue is obtained as a residue.
    The mixture is stirred for 1 hour 30 minutes at 90 ° C, then evaporated to dryness with 10 orange oil, which is diluted under pressure (2.7 kPa) at 150 cm of ethyl acetate. To this, 30 C. A precipitate is obtained, which is added to the purification solution by 18.5 cm 5.6 and. flash chromatography (eluant — solution of gaseous hydrogen chloride cyclohexane-ethyl acetate 90–10 by volume in diethyl ether. Formed). Fractions 12-18 are combined, then 5 precipitates are separated by filtration, then
    recrystallize from 70 cm of isopropanol. In this way, 12.8 g of methyl methylo-3-α-phenyl-3 phenylthio-2-propene (Z) hydrochloride are obtained and the mixture is dried to dryness under reduced pressure (2.7 kPa) at 30 ° C. Thus, 21.1 g of 4- are obtained. chloro-1-ethoxycarbonyloxy-1- (3-fluorophenyl) -2-phenyl-2-butene (Z) in the form of an oil pale-20 de white solid,
    yellow (Rf "0.5; eluent melting at 141 ° C.
    cyclohexane: ethyl acetate 50:50 by volume. According to the method described in example
    his).
    1-Dimetschiamino-4 ethoxycarbonyloxy-1CI-A- (3-fluorophenyl) -3-phenyl-2 butene (Z) can be obtained as follows. To 12.6 g of a solution of 4-dimethyl-, amino-4- (3-fluorophenyl) -3-phenyl-2-buten-1-ol (Z) as a free base in 100 cm of toluene was added 30 5 cm methyl chloroformate, the Mixture is stirred at a temperature of 90-95 C for 4 h, then cooled to a temp
    1, but based on the corresponding starting materials, the following products can be obtained.
    , Example 4. 4-Dimethylamino--1,2-diphenyl-2-butene-1-sl (Z), the hydrochloride of which is obtained in the form of a white To powder with m.p. 178 C.
    Example 5. 1-Cyclohexyl-A-dimethylamino 2-phenyl 2 buteH-1-ol (Z), the hydrochloride of which is obtained as a white powder with mp. 222 SPRIMER 6. 1- (4-Chloro-1-fe, environment) The precipitate formed is separated by filtration, 35 nsh1) -4-dimethylamino-2-phenyl-2-butene, then washed in isopropyl oxide. -1-ol (Z), the hydrochloride of which is obtained in a semi-image. 7.7 g of hydrochloride are obtained in the form of a white powder with mp. rata G-dimethylamino-A-ethoxycarbonyl-.
    rxy-4- (3-fluorofanil) -3-phenyl-2-butene. Example 7. 4-dimethylamino (Z) in the form of a solid beige- 40 -1,2-diphenyl-1-methyl-2-butene -1-ol (Z),
    i color, melting at 160 C. The hydrochloride of which is obtained in the form of This product is dissolved in 100 cm of a white powder with m.p. . illi water. Add 50 cm of Example 8. A-Dimethylamino-2-dichloromethane, then 10 g of phenyl-1- (3-pyridin-1) -2-butene-1-ol (2) bicarbonate, sodium, and transfer the mixture. .Organi- 45 sesquioxalate which is obtained in vi
     Cescal phase defend, then iodine, de white powder with so pl. . phase is extracted twice with 50 cm of di- Example 9. A-Dimethylamino-2-chloromethane. The organic phases are unified-phenyl-1- (2-pyridyl) -2-butene-1-ol (Z),
    one
    ole slowly at f) (, ds C 1 C 11 and 1 C) t 45 g H-ch.chor-1-phenyl-1-phenyl-1-propium (Z) as a solution in 40 cm of ethanol and continue to flow through for 14 h at room temperature (22 ° C. The reaction mixture is fed under reduced pressure (2.7 kPa) at 30 ° C. The residue is obtained as a residue.
    orange oil, which is dissolved in 150 cm of ethyl acetate. To this solution is added 18.5 cm 5.6 and. solution of gaseous hydrogen chloride in diethyl ether. The precipitate is separated by filtration, then
    1, but based on the corresponding starting materials, the following products can be obtained.
    , Example 4. 4-Dimethylamino--1,2-diphenyl-2-butene-1-sl (Z), the hydrochloride of which is obtained in the form of a white To powder with m.p. 178 C.
    Example 5. 1-Cyclohexyl-A-dimethylamino 2-phenyl 2 buteH-1-ol (Z), the hydrochloride of which is obtained as a white powder with mp. 222 SPRIMER 6. 1- (4-Chloro-1-fensh1) -4-dimethylamino-2-phenyl-2-buten--1-ol (Z), the hydrochloride of which is obtained in the form of a white powder with m.p. .
    and yuyat over yagni sulfate.
    filtered, dryed with 50 de white crystals with m. pl.
    lower pressure (2.7 kPa) at 30 ° C. In this way 7.25 g of L-di-methylamino-4-ethoxycarbonyloxy-A- - (3-fluorophenyl) -3 phenyl-2-butene (Z) are obtained. in the form of an orange oil (Rf "0.58; eluent - methanol: ethyl acetate 60t40 by volume).
    Example 3. To a solution of IA3 cm of a solution of megilamine in meta. Example 10. A-Dimethy - - (A-fluorophenyl) -2-phenyl-2-b OL (Z), a acidic oxalate which is obtained in the form of a white crystal of 55 t. Pl. .
    Example 11. 1,2-Dif-Piperidino-2-butene-1-ol (Z) hydrate of which is obtained in crystals with m.p. 195-196 С
    which sesquioxalate is obtained in vi
    de white crystals with so pl.
    152 C.
    Example 10. A-Dimethyl-amino- - - (A-fluorophenyl) -2-phenyl-2-butene-1-OL (Z), the acid oxalate of which is obtained in the form of white crystals with 55 tons. .
    Example 11. 1,2-Diphenyl-A-piperidino-2-butene-1-ol (Z), the chlorohydrate of which is obtained as white crystals with m.p. 195-196 S.
     fA
    Example 12. A-DIRTYL (l l- / -difc nJI-2-byten-t - (). N (Z), xjiop-t idrlt (1 received as white crystals, r.il. 1AO C,
    fl p and mep 13., 2-Diphenyl-4- - (1 pyrrolidinyl) 2 - butene -) - ol (Z), chlorine idrat which is obtained in the form of white crystals with m. 106 ° C
    Example A. 1- (3-Chlorophenyl) -4-dimethylamino-2-phenyl-2-butene 1-ol (Z), the hydrochloride of which melts at.
    Example 15, 1 - (3-Fluorophenyl) -4-dimethylamine -2-phenyl-2-1-butene 1-ol (Z), the hydrochloride of which melts
    at les c.
    Example 16. 1 (2-Chlorophenyl) -4-dimethylamino-2-phenyl-2-butene-1-ol (Z) with mp. .
    Example 17. 1,2-Diphenyl-4-methylamino-2-butene-1-ol (Z), which
    get in the form of white crystals with so pl. 90 ° C.
    Example 18. 1,2-Diphenyl-4-α-ethylamino-2-butene-1-ol (Z), which is obtained as a white powder with m.p. 82 C.
    Example 19. 1,2 Diphenyl-4- - - (2 pr-Op lamino) -2-butene-1-ol (Z), the hydrochloride of which is obtained in the form of white crystals with m.p. 88 s.
    Example 20. 4-Butylamino-, 2- -diphenyl-2-buten-l ol (Z), the hydrochloride of which is obtained in the form of white crystals with m. Pl. 155 ° C, Example 21 4-Allylamino-1,2-α-diphenyl-1-1-butene-1-ol (Z), the hydrochloride of which is obtained as a white powder with mp. 113 ° C.
    Example 22. 1-Dimethylamino-3H-phenyl-3-thiophenyl-2-propene (Z), the hydrochloride of which is obtained as white crystals with m.p. ,
    Example 23. 3- {4-Chlorophenyl-thio) -1-dimethylamino-3-phenylthio-2-propen (Z), the hydrochloride of which is obtained as a white powder with m.p. .
    Example 24, 1-Dimethylamino-3-phenyl-3- (4-pyridylthio) -2-bake (Z), the sesquioxalate of which is obtained in the form of white crystals with m.p. .
    Example 25. 1-Dimethylamino-3- (4-fluorophenylthio) -3-phenyl 2-propene (Z), the oxalate of which is obtained in the form of a white solid with t, pl. i63 ° C.
    Example 26. 3- (4-Bromophenyl-thio) -1-dimethylamino-3-phenyl - 2-propene

    five
    0
    (Z) x gp) 1 ilrpt KuTnpi fn iKiiiyiaKiT in the form of a white logger 41 prpin tn; with t. pl. 252 ° C.
    PRI and m. R 27. 4-Limetilminp-1, 2-dipheny. H 2-butenol (E) in the form of white crystals with t. Git. 113 C.
    Lap 28, 4-Acetoxy-1-dimethylamino-3,4 - fennl-2-butene (Z), whose oxalate melts at 156 C.
    Example 29, 4 - Dimethylamino- -1- (2-fluorophenyl) -2-phenyl-2-butene-1- -ol (Z), the hydrochloride of which is obtained as a white powder, mp 175 ° C,
    Example 30. 4-Dimethylamino--2 (3-methoxyphenyl) -1-feiyl-2-butene -l-ol (Z), the hydrochloride of which is obtained as a white solid with m.p. 166 C.
    Example 31. 1 -Cyclopropyl-4-dimethylamino-2-phenyl-2-butene-1-ol (Z), the oxalate of which is obtained as a white gloss t. 127 C.
    Example 32. 1-Dimethylamino-5 -5-methyl-3-phenyl-2-hexane-4-ol (Z),.
    hydrochloride which receive in the form of white powder with so pl. 163 S.
    Example 33. 4-Dimethylamino--1,2-diphenyl-3-methyl-2-butene-1-ol (Z), 0 the hydrochloride of which is obtained as a white powder with mp. 212 C.
    Example 34. 3- (2-chlorophenyl-thio) -l-dimethylamino-3-phenyl-2-propea (Z), the hydrochloride of which is obtained in 5 as a white solid with mp. 62 C.
    Example 35 3- (3-Chlorophenyl-, thio) -.1-dimethylamino-3 Phekyl-2-propene (Z), the hydrochloride of which is obtained in 0 as a solid belago substance with mp. 156-157 p.
    Example 36. 7D1 methylamino -3- (4-methylphenylthio) -3-phenyl-2-prop
    5 (Z), the hydrochloride of which) 1 is obtained in the form of a solid white. 97-198 p.
    PRI me R 37. 2-CZ-Chlo-phenyl) -4-d1gmet. Alamino-1 (3-fluorophenyl} -20-buten-1-ol (Z), the hydrochloride of which is obtained in the form white solid with m. pl.
    , Example 12 38. A-AMHHO-S, 2-cyphe-55 ncl-2-buten-1-ol (Z), the hydrochloride of which is obtained as white pyroshkast, pl. 80 C.
    Pharmacological testing. Toxicity.
    Onpe; u nrii4.T Irmdukta (LO),
    50
    koi rsch at (p9jibni-U-i RBpji.etiHH mishy m ypyvnet.: get 50% from Pia.
    Antagonistic action against ntiiipecctui, causing tetrabenum in rats.
    After subcutaneous administration to rats (weighing 130-170 g) of tetrabenazine at a dose of 10 mg / kg, after 15 min, a dormant state with intense prostration and ptosis is observed.
    The product to be tested is administered subcutaneously or orally 1 hour before tetrabenazine is administered. The animals are placed separately in clear glass chambers and monitored for 30 minutes, 1 hour, 1 hour, 30 minutes and 24 hours after administration of tetrabenazine. In each animal, the condition of the orbital fissure is noted: closed or open (at least half). The opening of the orbital fissure indicates the antitetrabenazine activity of the product under investigation.
    Take 4 rats for each dose and 3 or 4 doses for each product. AEj (effective dose 50) of the product is the dose that, at its peak, suppresses ptosis in 60% of animals treated with tetrabenazine.
    Anti-cataleptic activity against prochlorpemazine in rats.
    Prochlorpemazine solution is administered subcutaneously at a dose of 0 mg / kg (single dose containing 5 MP / kg in volume) of 5 rats. At such a dose, prochlorpemazine causes catalepsy in 80-100 hours at 5 hours % of animals, and this condition lasts more than 3 hours.
    5.5 hours after administration of Lrochporpemazine, oral physiological serum (control animals) /: or product under test (3-4 doses of the product) were administered in single doses in a volume of 5 mp / kg. Animals were tested for three stoppers after 30 minutes , 1 h 30 min and 2 h 30 min after the introduction of the physiological saline or the test product. The test with three plugs is that the animal is placed on its hind legs, its front legs are put on three plugs, placed on the other (total height 13.5 cm). The animal in the state of catalepsy maintains the position 5 in which it was placed. In this way, the dose of the product, kp- | hr, chi and; | n | and r gnschm. it iin ri C1 (, p: oG n; 1, set to, p. hlmpg. and (%
    animals (OS 50 L CRG) N; 1 AND L.PYA
    50% of animals) according to the ratio to I1. ptm
    control zhipptyhs.
    Resu; 1b trial.h are presented in the table.
    From the given 1.1x data nsi about that
    The proposed compounds are more active than znamelidine, a well-known anti-depressant.
    权利要求:
    Claims (1)
    [1]
    Invention Formula
    The method of obtaining 3-phenyl-2-propenamine derivatives of total rmula
    R
    -C C-CH9-11
    R
    Y-A
    RI B,
    (ABOUT
    where R is hydrogen or halogen, or
    C-C-alkyl or alxyl; R is hydrogen or methyl; R, and the same or different - hydrogen or C, -C-alkyl, which may be substituted
    G, -C4 alkenyl, or R, and R, together with the nitrogen to which they are attached, form a 1-pyrrolidinyl or piperidine radical;
    A is C-C-alkyl or phenyl unsubstituted or substituted by a halogen atom or C, -C4 alkyl, or A is a pyridyl, benzyl or cycloalkyl radical containing 3-6 carbon atoms; Y is sulfur or radical of the general formula
    45
    R - C - OR 5 (P)
    h, 5
    where R is hydrogen or methyl;
    Ry - hydrogen or acetyl
    Group,
    as geometric isomers or mixtures thereof, as well as pharmacologically acceptable salts, characterized in that ammonia or an amine of the general formula
    (MO
    1402251 O
    where R and RJ are given, except that Ry is not
    hydrogen either
    neither;
    subjected to interaction with a derivative of phenylbutane of the formula.
    E
    ..X (IV)
    Y is sulfur, which is in E or Z configuration, the npd process is carried out in ethanol or methanol at ambient temperature, then, if necessary, the resulting 1Q product is hydrolyzed and the product is obtained total (1), where Y is the radical of the general formula ( II), where R is hydrogen, and the remaining radicals have the given values and the obtained X-chlorine {15 product is isolated or when not Y is sulfur or the radical of the formula (II), is boosted and converted into pharmacology, where R4 R5 is a significant value salt.
    Y-A
    where A and R have given values of j
    100-300 About 135 100-300 100-300 About 400 About 265 100-300 SO-ZOO 100-300 100-300
     l
    RKOLO 400 100-300 About 90 About 265 100-300 100-300
    9.5 3.6 1
    7.5 1.1
     14 12
    1.5
    6.5
    eight
    2 14
    2
    I
    2.7
    1.8
    hydrogen either
    X is bromine;
    Y is sulfur, which is in E or Z configuration, and the npd process is carried out in ethanol or methanol at ambient temperature, then, if necessary, the resulting product is hydrolyzed and the product is obtained total {1), where Y is the radical of the general formula (II ), where R is hydrogen, and the remaining radicals have the given meanings and the product obtained is isolated or at 7, 5 4 7 5.2
    4 12
    five
    13.5 17.5 10 4 9
    7.5 3 „5 1.6 16.2 5.5
    1 0225112
    Prpdol; Yenir tlGmpip.
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    FR2559765A1|1985-08-23|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    US3978129A|1972-01-28|1976-08-31|A. H. Robins Company, Incorporated|Alkenyl- and alkanylamines|
    US4056630A|1973-02-24|1977-11-01|Beecham Group Limited|Diphenylpropylamines for treating depression|
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    US4996235A|1987-11-25|1991-02-26|Eli Lilly And Company|3,4-diphenylbutanamines|
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    DE10048714A1|2000-09-30|2002-04-11|Gruenenthal Gmbh|5-amino-1-penlen-3-ol derivatives|
    US20050176136A1|2003-11-19|2005-08-11|Dexcom, Inc.|Afinity domain for analyte sensor|
    CN103819400B|2013-09-16|2016-05-04|江西师范大学|A kind of synthetic method with dissymmetrical structure 1.4-dihydropyridine and derivative thereof of multi-component reaction|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    FR8402338A|FR2559765B1|1984-02-16|1984-02-16|NEW PHENYL-3 PROPENE-2 AMINE DERIVATIVES, THEIR PREPARATION AND THE MEDICINAL PRODUCTS CONTAINING THEM|
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