• 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:
    Imidazoline derivatives of the formula wherein R' is hydrogen or alkyl C1-6; R2 is hydrogen, methyl, chloro, bromo or fluoro; R3 is hydrogen, methyl, hydroxy, methoxy, fluoro, chloro or bromo; and their non-toxic salts. Processes for their preparation and pharmaceutical compositions thereof. The compounds exhibit presynaptic α2-adrenoreceptor antagonist activity.
    公开号:SU1204134A3
    申请号:SU823467047
    申请日:1982-07-26
    公开日:1986-01-07
    发明作者:Борн Чаплео Кристофер；Лесли Майерс Питер
    申请人:Рекитт энд Колман Продактс Лимитед；
    IPC主号:
    专利说明:

    From (brend of O1-io;: kchch; to obtain HOiibix production; 111i; x
    Linden ( .
    f. IT-i
     0 t
    pz
    rt r
    RT nodorsd, methyl or Kj: op g R, Eodorsch) gyiJ: ,,;: c c; i-g rumg l
    -J- .--.
    M VrOKv; Hrpyiina,;) GOR. what;; or SpCMj or srx. KS: S: CG: Draft :;
    salts, possessing ds: a:; ь; m pharma cholo) ichhos-kt1mi gn (;; m ;;:;
    MI;
    The goal of izebrs-geni is 1; and the HGS z. Kshy :: s.oediniiiyz possessing tssshtygp-: :: l - - p; lolog ich1: k1 1I svotokzza,
    Example 1, Hirrgilr ;::: - (5-fluoro-2 J 3 -l; igidrobeizofura1ti, g:. 5 Fts; fbenzofurai -karbsi:; 1 n ;; acid
    Persim-eshiyayug 4: L1 g g -ft (;; р; a.: I;: uir of lovogo aldehyde ,, 11.3 g v. Malong1ta and 35 ml of methyl ethyl I-OIKI Add b;: z-code carbonate Ka.-ivi - f (8.7 g). V. to the demolition of the demolished.) Lipsticks g: sbra-g lb # t-cc: toklytyhom: H: Dpbl lut excess uncompletedly; -hrm hm: n to: uchg: t1nuy mixture extragir - are dit 1 Shkli) 1m 3d) HpoNi. Submission :; - ;: extracts are ptyunyvayu: node, wok ui: ivevat:; i scream: arypayu; to, ks ;;; ik erabatyln: 1yu K) weight. / s - a-reverse refrigeration; . S; type BOjiHTejii-. Pyaarit, to the rest of them work:; 1; bg; com sarnpt; ki and quickly 1agrg: nayat Larsvsy After cool: 1japii; cheese: sour; filtering; -, and cut, g (b); c:; crystal; izatsi: mz mixture of ethyl ethanol iiojiynaiO v yellow j-c; |; a 1-o - cc: p product (i, l i) with icaj: -;
    Acid (2 44-) is added to the zoisis solution of sodium hydroxide 3, sodium hydroxide p 5 (1 ml of water). Amalysh sodium, loluchsnnuyu HLS, g) is added over 20 min;; and
    and 42 grams of mercury. Later SLEEP 3 W h;.). I
    the thief is left standing: a -; are
    A solution of 0.16 g of ethylenediamine in ml of methanol is added before and after the cells. After 15 minutes, a solution of hydrochloric acid in methanol (about 1 molar equivalent of HCP) is added dropwise with cooling, after 2 hours the methanol is removed in a vacuum, and the resulting residue is partitioned between chloroform and a saturated aqueous solution of sodium bicarbonate. The free base is extracted with chloroform, and the combined extracts are washed with water and dried. To the chloroform extracts is first added ethereal hydrogen chloride, then diethyl ether, and the precipitated salt is filtered off to give 0, D4 g of the product with t, kip, 209-2ig C (with decomposition).
    Example 2. Chlorohydrate 2- (2- -me to-2, 3-dihydrobenzofuranyl) -2- -imidazoline,
    Prepared from 5-methoxy-2,3-dihydro-benzofuran-2-clrboxylic acid as in Example 1 (c-f), m.p. 209-211 V (with diff.).
    Example 3. Bromhydraa-2-- .- (5-OXI-2, 3-dihydrobenzofur yl P -2-imidazoline.
    , 5 g of the free base obtained from hydrochloride (5-labels, 3-dihydropane} zofyranil) J -2-them - dazoline, treated with 48 wt.% The volume of hydrobromic acid solution (15 ml.), And the resulting mixture is heated at 100 within 7 hours with stirring. After evaporation of the solvent, a solid residue is obtained, which after recrystallization from ethanol / diethyl ether gives the desired imidazole hydrobromide (0.5 g). M.p. 231-235 C.
    Example 4. (a). Hydrochloride- (2-methyl-2,3-dihydrobenzofuranyl) 3 -2-imidazoline,
    2- 1 methyl-2, 3-dig-idrobenzofuran-2-carboxylic acid, it is prepared in two different ways.
    A. (i) 2- (2-Hydroxyphenyl) -2-methyl- - 2, 3-epoxypropane.
    A solution of 72.8 g of methachlorobenzoic acid in methylene chloride (900 ml is added dropwise over 3 hours to a stirred solution of 48.1 g of 3- (2 hydroxyphenyl) -2-methyl-prop-1 ene in 450 ml of methylene chloride, xoLo - in an ice bath up to 10-20 C, the resulting mixture is stirred for another 24 hours, and then filtered
     for distance1; eta-chlorobenzene acid; The filtrate is washed with: 10 wt.% vol. aqueous solution of sodium sulphite (500), saturated aqueous bicarbonate atri and finally saturated: 1: brine, the organic phase is evaporated in vacuo to obtain target epoxy (52.7 g) Rf 0.37.
    (ii) 2-Oxy; ethyl - 2-methyl-2, 3 d and g and rb e n 3 o f f r at ;,
    A mixture of 52 J 7 g 2- (2 oxyphen-1-sh) -2 -2-methyl-2 5 3-epoxypropane and dv, silica (Kisselgel 5 60
    70-230 meshes) (50 g) in 300 ml of meth: g-chloride is stirred at room temperature for 24 hours. After removal of the solvent, silica and absorber are obtained in the residue.
    rOb; 1N product, and this mixture is stirred with ethyl pate for 3 hours. After filtering, this 1-step filter is drained and the solvent is evaporated in vacuo to nons eHHH target alcohol 49.6 g. This crude product is dissolved in methylene chloride and
    ppom:
    n, hydroxide solution
    thirty
    B Ggry in water, water, and then dried. After the solvent is obtained, alcohol is obtained as a yellow oil.
     1 to with
    3200 cm
    (i i i). 2 ms gil-2, 3-dihydrobenzofuran-2-carboxyic acid,
    16.4 g of 2-hydroxy-methyl 2-methyl 2,3-dipyrobenzofurpma and 5.2 g of potassium hydroxide in 50 ml of water were mixed and cooled to 5 ° C. 20 g of potassium thermanganate were added in 45 minutes to overpowering
    TeNmepaTvpv which
    ABOUT
    the swarm is kept below 12 ° C. After the addition is complete, stirring is continued for 1 hour, and then the resulting mixture is diluted with water. Sodium metabisulfite is added to resolve the precipitated MnO, followed by the addition of an excess of sodium carbonate. The aqueous aqueous phase is washed with methylene chloride and then acidified with 2 Ng of hydrochloric acid. As a result of the extraction with methylene chloride, followed by washing, drying and evaporation of extracts of. 3.0 g carboxylic acid, IR spectrum: d, (s, s 1720 cm
    in a flask with soutsim argon z: g ru: ;; Yu diisopropshamin (8 ,, g ssschexegeret; - one with hydrocalcium) and te r.gilro 4uran (120 ml) with IgG1rits; M qnpcv elastic stopper: Peremeshkv; -Eggy solution; SO,: According to ka g m; a 5 - 10 min addition of h - butyl lactium (1.6 M fi hexane, 35 ml) and rk :: luch; mixture is allowed to cool
    lazy ;: eni to - / C With a drop w / v of tzl:; - there is a solution of 2, 3-dhydroben 50f -rag1-2-carboxylic acid (3.3 g of 30 ml of tetrahydrofuran) with a mixture of orange-colored red ozvstvo- pZo After 20 min obscTpo add
    passing through a column of silicon dioxide to a distilled) This occurred almost immediately;
    Connection example
    G. C (g
    f; ; .LIHORORIDO-} X
    hrmpgs extracts lrtsnayu to p (/ radiation
    a u b o m o c. M to u (l:} Th;
    Me - methyl. Characteristics of the compounds obtained
    247-250
    With „, NA
    I-propyl
    246-249
    C ,, H, gK, 0, HCl
    I-pentyl
    221-224
    C ,, NA
    "5O-propyl
    258-261
    . HC1
    13
    7-Me N
    8.22
    neny given in Table. 2,
    Table
    with 61.78; H 6.78; N 11.08
    61.46; H 7.11; N 1 1, 01
    C 62.50; H 7,21,41
    (G 6 4, 4 f; H Y,, T6
    C 65.18; H 7.88; N 9.50
    C 65.19; H 8.22; N 9.70
    C 63.03; H 7.18; N 10.50
    C 62.84; H 7 30; N 10.58
    1, Pre- and postsynaptic to her - adrenoreceptor antagonism in the ex- periment with isolated tissues.
    The initial biological assessment of presynaptic pi -adrenoreceptor antagonism is assessed by the pAg value in comparison with the inhibition of the selected conditions of exerter) {all ex: themed compounds, with the exception of mianserin, give a complete change in the inhibitory effects of clonidine on the hypogastric nerve syndrome. The maximum change is observed for mianserin and is 36% at a cumulative B-dosage of 4.4 mg / kg. From tab. 5, it can be seen that the compound of Example 5 and phentolamine are approximately equivalent against the in vivo presynaptic 1} C -adrenoreceptor stimulatory effect of chlonidine. In vitro data showed that presynaptic sat-adrenoreceptor antagonist (Table 4) is approximately 8 times more effective than yuhimbin in decapitated rats (Table 5).
    3. Presynaptic ' -adrenoreceptor antagonistic and post-naptictic ' 1 -adrenoceptor agonistic activities in experiments on isolated tissues.
    The compound of Example 6 is an image of a compound that possesses both presynaptic anc-adrenoreceptor antagonist 0 (1 -adreporeceptor antagonistic and postsynaptic OC -adrenoregdeptorant agonistic activity. Presynaptic an-adrenoreceptor anchor antagonist antagonist agonistic activity). 1, The postsynaptic ct -adrenoreceptor agonist activity is expressed as pD2, which is the negative logarithm of the molar concentration of the compound giving 50% maximal abbreviations (in (ancococcygens muscles).
    this case
    In tab. 6 shows the result: for the compounds of Example 6 (1, B. R, R H), analogous to the dehydro compound A and the postsynaptic agonist activities of chlonidine and (1enyl efrin). The results obtained are averages of at least onbi j OB and show that the compound of Example 6 is a presynaptic H. antagonist more than 200 times stronger than a similar dehydro compound. The dehydro compound is essentially a postsynaptic antagonist with a p. 5.24 in a study on anococcygens muscle of rats.
    about l and c
    3.50
    6.08
    -
    6.3
    7.5 6.5

    four . Presynaptic to -adrenoreceptor antagonistic and postsynaptic co-adrenoreceptor agonist1G-1eska activity in depressed glands of rats.
    In vivo, presynaptic ai -adrenoceptor antagonistic activity is determined according to the methods described in section 2. The postsynaptic agonistic activity is determined on a separate group of decapitated rats and expressed as an intravenous dose of the compound that causes an increase in diastolic blood pressure 50 mm Hg The results are shown in Table 7,
    As a result, it can be seen that, both in insulated tissues and in inserts; Animal 5 The compound of Example 6 has presynaptic adrenoreptic antagonistic properties. In addition, it is slightly stronger as a post-HEP-iecc Karo cvi adreporeceptor agonist.
    Table 7
    five
    0
    five
    Compound
    By 6 Hlonidia Phenylsfrin
    An intravenous dose causing a 50% change in the h. pidin-like bloc in Vas deferens
    0.030
    Intravenous medication
    awesome
    boost
    on
    50 mm Hg
    diastoli
    chesky
    pressure
    of blood
    0.020 0.003 0.030
    权利要求:
    Claims (1)
    [1]
    1. The method of obtaining imidazoline derivatives of General formula I
    where K ( ”hydrogen or C -C 6 -alkyl ; p. 2 is hydrogen, methyl or chlorine;
    - hydrogen, methyl, hydroxy, methoxy, fluorine, chlorine or bromine
    or their non-toxic salts, about t and being the fact that the compound of the general formula II
    where K is hydrogen or C ( -C 6 ~ alkyl;
    K ™ is hydrogen, methyl or chlorine;
    1C - hydrogen, methyl, methoxy group -
    pa, fluorine, chlorine or bromine;
    K. is methyl, or ethyl HX is hydrogen chloride,
    are reacted in an alcohol of the general formula HON with at least one molar equivalent of ethylenediamine and then the resulting compound of formula I, where K - methoxy, treated with aqueous bro - mistovodorodnoy acid to obtain a compound of formula I, where R e oxy group,
    2, The method according to π, 1, characterized in that methanol or ethanol is used as an alcohol of the formula HON.
    at
    WITH
    >
    Isbretsnie refers to the method of obtaining Pony derivatives kmadlyu linden upholstered Fortune [I
    where K ( is hydrogen or C. u-loku
    K-g is hydrogen, methyl or ULOR;
    I, 'hydrogen, methyl, ldsrusht
    methoxy group, fluorine, chlorine OR brSM, OR THEIR NSLLDDNTL with salts possessing to others
    f a ρ m a x o l o h i c e o c i m i l l zl
    MI;
    The purpose of the invention is about drank ;, compounds with valuable packaging with similar properties;
    Example!, Ylorohydr; · ’" tr.l - (5- "fluorine — 2., Z'hlptpidrobepzofuryl; -imide solane a,
    p 'ί. 5 ~ F'G’Orbenzofuran ’’ 2 ’harboy; whether acid,
    4.6 g of g-f-gerulpst of new aldehyde is mixed, H, 3 tons of dme / lbl ·: -malonate and 35 ml of methyl ethyl gon,
    Anhydrous potassium carbonate is added (<8.7 g), and the resulting mixture is heated under reflux for 6 s, Debel the excess dilute sulfuric acid kit, and the resulting mixture is extracted: - from dstiltyl ether., The combined extracts are washed, poured, dried and evaporated to an oil, hsleroy
    process And) Nays volume: Mr. .....
    with a bare CPC (30 ml) and boil for a reverse manhole 43 minutes, the driver will evaporate and the residue; L- ~ ~ work with a sulfur sylcl,
    And quickly heated on a narrow ban ;; After cooling, the crude acid filter is filtered; As a result of recrystallization from these mixtures; molded ethanol get gentsnaplksr; c - with the product · (I to) with smol "· 6
    (with,), Ih-ntektr; '2,.,. ,,
    = 1685 cm ' 1 .
    <B d 5 — Fluorl, 3 ..... digndreyondi; lute
    —2 — carboxylic acid,
    44>
    f4z2y:
    H. · ; '' · '7 : · n) 4 (4 CHNy'CH ί
    .....
    7th <- '·': dsn ' : E: H ·
    h :-)) 44 4443444-4 hh 4 44 (44 (4-4 4 4, (’з.
    '^ •' - '4 CHCHCHCH in "GS
    π ; pd; and .l;: .. Oh! H YT L . '-'63 Ln (4) 44.4 (' · ('(l: rcho:
    } lh i-Ch'ch l.4h. from rilch chchchl 'Chlch- -'g; h ί ; g h:: 'hh. <• '• -.'P-'CH'CHG'rCH--l', ChSg .44.4 (44 4 • 442''4) 4 4 44. Pan, 4 4 4 4 and H 2.4
    : pH pC '-: 0i and C and 4 hrme ~~
    • Evil "4" 3 34244 rass4. · -4 -4422-: '44 44) 4) -3. 22,: 4 '·: 4' · '4 4 y 4 2’4: 44434- CheHC; 4 With ““
    4 44 4 44-4--44444 27 4444 H44HCH
    4:44 C: C 4 4.444 34
    four ;. b 4)
    3 4 4 ‘444
    4p-'4 .444 4; "44ro ~
    '43444; Е Р 421 4245444-1 g about cap ~
    4 34 fzru a'O'ZG X.4 4 34.44 4 НС-44 '5242 strength
    -4 ; four
    1.44.4
    '44 G
    44 · 2-444 44 TO KOM ""
    4 '444 - 2.42 ^ 4 444) 42 4 4 44
    044 4 l. '"2454-FIL4p <4 ~“
    ; 4 ЗЗ 4- '4 440' 7 4224 3 7414И
    • ' : 4 4 К4рООК <' 441И. '. four
    4, :! , 4 '-L' l 4! <:
    . 4 "4 g h. 42Ч4 and a.ro-, 444.-44444) '• L. ··! A 4
     four : . · L 2 :: -: 4 4 44
    4 ': ·' 4 (4) 2 (44 O other
    H) : 44; H 2244 (444
    ll 344.5444
    :· four! 44 44 42 And p comfort ..
    442 4! ' And '44 24:14
    ; - ((Π- · 4 "
    ': 4.1 4 0404
    - 42; . 22-444 4НЯ 4 НСр 4 (4 40 Pro-4 44.4-: 4 2 5- ~ Fluorobenzofue1G - 2 "“ carbsno1; th acid (2.4 e) is added to a water, sodium hydroxide solution (2.3 p sodium hydroxide l 50 ml of water). 2
    add over a period of 20 minutes; and: sodium bake obtained from; ί g sodium and 42 g mercury, After another 2.3 hours, the thief is left to stand over;
    4- '4 - "- 4-4. L4- 4 9 dl“ of imidol choline: · 44- DpGzMANYAT l: 4.44-- X35 4
    '44 - 1 ' 4424.444: 44 ') 24' 4 4
    R.Ch.44—
    3
    I 20ά
    four
    to give e 0 C and a solution of 0.16 g of ethylenediamine in 1 mL of methanol, later! 5 minutes while cooling with a solution of hydrochloric acid in methanol (approximately 1.1 molar equivalents HCP) After 2 hours, the methanol was removed in vacuum, and the resulting residue is divided between chloroform and saturated aqueous sodium bicarbonate. The free base is extracted with chloroform, and the combined extracts are washed with water and dried. To chloroform extracts, first etheric hydrogen chloride is added, then diethyl ether, and the precipitated salt is filtered off, whereby 0.44 g of product are obtained with t, whales 209-219 ° C (with decomposition).
    Example 2, 2- (2-Me'-oxy-2,3-dihydrobenzofuranyl) -2-imidazoline hydrochloride,
    Prepared from 5-methoxy ~ 2, 3-dihydrobenzofuran — 2 — carboxylic acid, as in Example 1, m.p. 209-211 in C
    (with),
    Example 3 Bromhydrate-2-£ - (5 ~ hydroxy-2,3-dihydrobenzofuranyl]] —2 — imidazoline,
    1.5 g of the free base obtained from 2- [2- (5-labels — si — 2,3-dihydrobenzofuranyl)] -2-hydrochloride-2-dazoline are treated with 48 wt D of hydrobromic acid (15 ml), and the resulting mixture is heated at 100 ° C for 7 hours with stirring. After evaporation of the solvent, a solid residue is obtained which, after recrystallization from ethanol / diethyl ether, gives the desired imidazole hydrobromide (0.5 g). M.p. 231-235 ° C.
    Example 4. (a). Chlorohydrate-2- [ - (2-methyl-2,3-dihydrobenzofuranyl) 3-2-imidazoline,
    2 - "1-methyl-2,3-dihydrobenzofuran-2-carboxylic acid, it is obtained in two different ways.
    A. (ϊ) 2- (2-Hydroxyphenyl) -2-methyl - 2,3 — epoxypropane.
    A solution of 72.8 g of methachlorobenzoic acid in methylene chloride (900 ml) is added dropwise over 3 hours to the stirred solution, 48.1 g of 3— (2 — hydroxyphenyl) -2-methyl-prop-1-ene in 450 ml methylene chloride, cooled in an ice bath to 10–20 ° C, the resulting mixture is stirred for another 24 hours, and then filtered
    There is no need to remove meta-chlorobenzoic acid. The filtrate is washed successively with 10 weight% by volume with an aqueous solution of sodium sulfite (500 ml), with a saturated aqueous solution of sodium bicarbonate, and finally with saturated brine. The organic phase is dried and evaporated in vacuo to give the desired epoxide (52.7 g) K £ = 0.37,
    (ίί) 2-Oxymethyl-2-methyl-2,3-dihydrobenzofurai.
    A mixture of 52.7 g of 2- (2-hydroxyphenyl) -2-methyl-2,3-zpoxypropane and silica (kisgel gel, 60;
    70-230 mesh) (450 g) in 300 ml of methylene chloride is stirred at room temperature for 24 hours. After removal of the solvent, silica and an absorbed product are obtained as a residue, and this mixture is stirred with ethyl acetate for 3 hours. Polle filtration the ethyl acetate filter is allowed to stand and the solvent is evaporated in vacuo to obtain the target alcohol of 49.6 g. This crude product is dissolved in methylene chloride and washed with 1N sodium hydroxide solution in water, followed by drying, and then dried. After removal of the solvent, alcohol is obtained as a yellow oil (37 g). IR spectrum; 3700 3200 cm ' ( .
    (ί ϋ) <2-Methyl-2,3-dihydrobenzo-furan-2-carbonic acid.
    16.4 g of 2-hydroxymethyl-2-methyl-2,3-dngidrobenzofurana and 5.2 g of potassium hydroxide in 150 ml of water were mixed and cooled to 5 e C, is added 20 g of potassium permanganate in 45 minutes to a stirred mixture temperature koto - the swarm is maintained below 12 ° C. After the addition is completed, stirring is continued for 1 h, and then the mixture is diluted with water. Sodium metabisulfite is added to destroy the precipitated MnO ^ _, followed by the addition of excess sodium carbonate. The main aqueous phase is washed with methylene chloride, and then acidified with 2N hydrochloric acid. Extraction with methylene chloride followed by washing, drying and evaporation of the extracts yield 3.0 g of the carboxylic acid.
    IR: 1720 kc sm'4
    B. 2-Detil ~ 2,3-dihydrobenzofuran — 2-carboxylic acid,
    five
    Diisopropylamine (8 сух 1 g hyogeon guards with hydrocalcium) and dehydrofuran (120 ml freshly sterile nakns-t'o with lithium aluminum iyihydride 5 syringe chegro g elastic stopper are loaded into a flask with dry argon and cooled in a flask with a mixture of lithium aluminum and hydride). using a methanol / CO bath, n-butyl lithium (1 M in hexane 5 55 ml) is added dropwise in 5-10 minutes and the mixture is allowed to cool to room temperature
    temperature After re oh __ o
    Preparing to - / 8 C dropwise add a solution of 2, 3-dihydrobencofuran-2 ·· “carboxylic acid (3.3 g and 30 ml of tetrahydrofuran) with an immediate formation of an orange-red solution. After 20 microns, methyl iodide (10 g, fresh moonlight passing through a column of silica and distilled) "At the same time,
    five dt : .Nt mon out ' (about I am in ye [ H I bn adno / y π p 'in about ;;) Later 's labor on Nnu't dztt In YPSh UYUT on DR.N and
    with g! ’; n ·: ruby mt and ilenchloride 13 x x) Paul mrpp other extracts you soup“ I have been excreted to produce!
    SU By ZZZL''epoctou and TLC Idea ™
    V- zoyuyu ey zzuguu usyy kyyspt OhKeyaway software method Λ.
    You . Zdorojidryau "Y- *;" Y "(" -methyl ™ court and general efu rpnpl) 1 "2-imida- get az Y-yo-ul ..... 2 e 3-diz'id—
    c -: c p / w-y; kgsononic acid
    Ygrlmera ί Zssu 73 id,
    'KYzch: Oriyaeleuy other soldiersV I -; FORUGULU; : oud K, - hydrogen, obuch! What is the example of u or u yot · y th lines 3 and 33)
    3 'and with and and a 1
    6 And with
    7 n 6-do
    9 Ny-Me
    10 and evil
    Ζ N n ····; -; (' 1 i(e . ! four H 15 7 ”T 1 sixteen ά-me 7-Me 17 5 ™ Me 6 — Not 18 5 — Me 7-Me nineteen 5-C! / 'C I
    7
    1204134
    Continued table. one
    one 2 3 four
    20 6-C 1 7-C 1 HC1 308-310 21 5-С 1 7-Me HC1 245-266 (dec) 22 H 6 — he . NVG 249-254 23 H 7-OH NVG 234-241
    Me - methyl.
    The characteristics of the compounds obtained are given in Table. 2
    table 2
    TO, 0M.p. Formula Elemental analysis: R Calculated% Found 7
    Ethyl 247-250 C. 3 H 16 P g O, HC1 with 61.78; H 6.78; N 1 1, 08 with 61.46; H 7, P; N 1 1, 01 K-Propyl 246-249 C, 4 H, 8 H 2 O - NA! with 62.50; AND 7.21; N 10.41 with K4 ', 47; n lying N Τδγπ N-pentile 221-224 with | 6 n 22 p 2 about · NS] with 65.18; n 7.88; N 9.50 with 65.19; n 8.22; N ΙγΤο "So -propyl 258-261 С, 4 Н (, П 2 0 · НС1 with 63.03; n 7 18; N 10.50 with 62.84; n 7; thirty; N 10.58
    The closest analogue of the proposed connection is
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    同族专利:
    公开号 | 公开日
    IE53389B1|1988-10-26|
    FI822551L|1983-01-29|
    IL66353D0|1982-11-30|
    PT75329A|1982-08-01|
    DK160275B|1991-02-18|
    IL66353A|1985-08-30|
    AU549166B2|1986-01-16|
    CS229938B2|1984-07-16|
    JPH0233038B2|1990-07-25|
    HU190023B|1986-08-28|
    DK160275C|1991-07-22|
    GR76210B|1984-08-03|
    IE821789L|1983-01-28|
    EP0071368B1|1985-04-17|
    DK335682A|1983-01-29|
    DE3263123D1|1985-05-23|
    DD211349A5|1984-07-11|
    FI67545B|1984-12-31|
    NO157215C|1988-02-10|
    NZ201219A|1984-10-19|
    ZW13782A1|1982-10-06|
    ES8307796A1|1983-08-01|
    PL139439B1|1987-01-31|
    ZA825164B|1983-05-25|
    PT75329B|1984-07-31|
    NO822568L|1983-01-31|
    AU8643882A|1983-06-02|
    US4411908A|1983-10-25|
    CA1171864A|1984-07-31|
    PH18878A|1985-10-22|
    ES514359A0|1983-08-01|
    FI822551A0|1982-07-20|
    NO157215B|1987-11-02|
    PL237655A1|1983-03-28|
    FI67545C|1985-04-10|
    EP0071368A1|1983-02-09|
    AT12769T|1985-05-15|
    JPS5826884A|1983-02-17|
    引用文献:
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    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    GB8123271|1981-07-28|
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