• 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:
    A process to prepare compounds of formula I <CHEM> in which n = 0, 1 or 2 comprising the cyclisation of compounds of formula II <CHEM> in which n - 0, 1 or 2. The cyclisation may be effected in the presence of an organic or inorganic base or thermally at a temperature in the range 40-160 DEG C. Compounds of formula II and certain analogues thereof are disclosed as cardiovascular agents.
    公开号:SU1766255A3
    申请号:SU894614311
    申请日:1989-05-17
    公开日:1992-09-30
    发明作者:Маклин Лэчлан；Ллойд Робертс Дэвид；Бэррон Кеннет；Джон Ничол Кеннет
    申请人:Дзе Бутс Компани Плс (Фирма)；
    IPC主号:
    专利说明:

    Ncho
    l CH3
    and the resulting compound is reacted with a halogenating agent such as sulfuryl chloride in dichloromethane at a temperature below 1.5 ° C. to form a compound of formula V
    ABOUT
    II
    Ncho
    CH3
    where RI is halogen; R2 is halogen or hydrogen, and
    The resulting product is reacted with a sulfurous nucleophilic agent in the form of a methanethiolactanion, such as sodium methanethiolate, in a solvent such as a mixture of dichloromethane and methanol, at a temperature from 0 to. to form a compound of formula VI O
    .CCH2SCH3
    NCHO 1 CH3
    five
    0
    tanom (J x 2c-o ml, / .sn. up-zriinn on the crystalline,; K: / I p5kt (.; in g: s; | uch-.: .- сг solid product.
    With recruitment - -: /; : /; 3 gvksane get 1- (4-ftpp-2-letilЈ;.: -ICphenyl; -2- (methylthio) ethanone. T. 61,5-53 ° C.
    Example 3. A mixture consisting of a solution of meth. Pg3.min e psomuscular denatured alcohol (%. Wt./mass of mental denatured alcohol: (60 fluoroacetofcon, 5 1 6 powders (0.7 Bg), load is heated to 2. By:;. 1 ice lane to 3C1 C rails of Euoru capaciously;
    water (30 ml). The mixture is heated under reflux by stirring for iO min V-, filtered over water (300 ml) is added to the filtrate and the solution is boiled with olodylonic oil. hot solution of 5 M hydrochloric acid was added to the solution. 90 ml and the reaction mixture:.: .- with a condenser for a short period. The reaction mixture was cooled to ambient temperature and an aqueous solution of sodium hydroxide ( 5M, 30 ml). The mixture is extracted with dichloromethane (600 ml), s is then re-extracted with dichloromethane (200 ml). The combined extracts with dichloromethane are dried (magnesium sulphate) and, after evaporation in vacuo, a crude brown oil is obtained. The resulting oil is distilled in vacuum (bp. 90 ° C. 1 mm Hg) to yield 4-fluoro-2 - (methyl; chino) etsetophenone, m.p., 52-53 ° C.
    Example 4. A mixture of acetic anhydride (44 ml) l of formic acid: (30 ml) stirred v. heated to 560 ° C in a nitrogen atmosphere for 2 and. The mixture is cooled to ambient temperature and 4-fluoro-2- (methylsmino) 3; 8 pF & non (27 8 g), prepared according to the procedure described in Example 3, is added in portions over 1C min, maintaining the temperature below 30 ° C. The reaction mixture is stirred at ambient temperature 2 - ;. t then cool
    ed
    : hold
    temperatures below 30 ° C were added simultaneously alternately with water (60 ml) and an aqueous solution of sodium hydroxide (specific gravity 1.5, 9-- ml), the mixture was filtered and the resulting layers were separated. Drive ;, l Spray dm chlorine methane (2 x 50 ml}, then zyderzhivr.-oi in a nitrogen atmosphere and dosing chlorine. Dichloromethane solution mix with e,
    then pru BSE P. yu drop by drop about T8chzg-, pz 40 min. keeping tomgeraturu below 1,5WC
    dichloromethane (60 / hl). After stirring at a temperature below 0UC for 1.75 h, water (140 ml) is added to the strainer for 30 mN while maintaining the temperature at 30 ° C. The resulting layers are separated and, after upgrionium ocra -iw-iecKoro els E vacuum, a mixture is obtained consisting of 2-chloroacetyl-3-photo-M-metALAformanilide and 2-dichloro-ethylate l -5 - Fto r - M - meth and l for r ma n i-l and in the foma of reddish-brown oil.
    The resulting mixture 47 g) is dissolved in a solution containing 1.4 d-scan (270 ml), zod (30 ml) -, i hydrochloric acid (2M, 4.5 ml), followed by boiling it under reflux for 1.75 h. The reaction mixture is cooled to a temperature: ambient: and evaporated in vacuum.
    The residue was dichloromethane (150 ml), and then the solution was washed successively with a saturated solution of sodium bicarbonate (50 ml) and aode (30 ml). After evaporation of dichloromethane in vacuo, a mixture of 2-chloro-1- (4-fluoro-2-methylamino-chenyl) ethanol and 2,2-dichlor-1-1 - (A-fluoromethylolane and ofane and l) is obtained. o0
    but
    on in the form of greens TS-brown oil, which otszhdzhetsts: ozna; -: -: n.
    The mixture (ii2.4 g) pc-iTsopino i g dichloromethane (24P i-. L) m is cooled to 0 ° 0 e of an ice bath with ice &amp; Imprint: Goth; -; Metno ny / g-EU: Eor ./ie.TS -Ti- .L:; ivs: -, / p.ji - i.-. (2.52 ml of ml; priZl. H -to, -.-: l m F for 35 min. -iHvKj s; Monsieur Ostopenng;: -.-- grind to teirerer. pchi; zhuyu; e: - medium; After 1.5;: mixture with acid (5 mol / l. 30 mp.) e avCM dilution t soda (120 ml).
    GcpSSOSSBL.iy 8THE LAYERS REH DYLA.OT. VI
    the smooth phase is scrapped l .-; chlorme 1NHO -1 (00 ml). After it is evaporated -, - 11 o5 eaten nenp; x organic layers in a vacuum field. frequent flax OB hundred brown m layer. C -; lt:.: - by the &amp;:: gokogffe: - t i: but o
    LIQUID HROMETHOGRAF1 1--; C H POL-30 - .. I eat 7 - 4 -; - .-, ches. vg.sda ivpoo model / LOG1 A with: p.p.par: r; nm.
    Ratsts-lochnich: m patron Dzuskisle space-l F rep P A H (T 1; 500. After
    Lein; 7 ether (...}. 60-ZE ° С) (00: 2) ROG Saskhede 250 ml / min sang; - (-: - fluoro-G-methi 1 aM / iHCc-e: -; / l) - 2 - (; -. T-Ti-i;: T i-io). 3T; ; f-: o:
    uh
    k -; slots; .2 ml), germmo-. l :: -; 3c: -:: - ... are psi 50-CO: С Е and мсс-бсо nitrogen 2 -. oaiv- c - onng the mixture I cool the OS with the temper L r; h och zhs: osh, it will be added to it among 5 m / n 1 (-6-mountain-2-мyТ 1Л5мичоо: -: -: l) V- (M .: - Til-g- / o; 3T5: - ;, 0 ;. psluchekn,: n znz / o,. MeTO.i, CN-. described by Bp;; trie 4.
    the lane of the surrounding land; oh dl oh, erc sane with l. d o m salt yu with the subsequent addition, water: schO; - z teien, -: e 30 m: ln. Godde H.-тa tzgmsr - /; vr; 1
    are d.shlsrmsganom (2 x 25 ml) of hectares niches; I1;: Sedi CG,: from. they are washed with water (2 x 20 m / 0. and then evaporated in a vacuum with a high flow of the product. O HCTKV of the specified flow of the dry drying stock and liquid liquid crystothers / Used /, bm systems. Gilson, s5zo,:: ozn- Oh 50.0 mgl Syn Vii, -; on dioxide: femn ::. and when copied with, mixtures of solvents dichtoome an / mets nol (99: 1; psi 1G ml / min I get: 5-fluor- -methyl-2 - (mЈticht;: e) xstilfomg: - nilid in the form of a pale yellow color band.
    Example b Pdcinoj C1 Ј, „5-fluoro-M-2 - (methylthio) and i-decay v - (0.68 g), obtained obtained knew L4i-nN ei described in pr1 / measure 5 v2-met: 1 p (30 ml) boil with another one. II ii. Reverse khoptsigo- i, 131 ° C, are kept in water / p with te, the mixture is evaporated in, e s .. g / g of solid product (63 o t) 131 le co- For the sample of the specified solid, p, (028 g), from the technical price pas, 7-fluoro-1-methyl-3-1 light is obtained 1s nolol, mp 158 5-160 ° С (008 g)
    Example 7 A mixture of state, 5-fluoro-M-methyl-2 - (methyl hyio) and nilide (2.00 g) of prepared ke, similar to that described in sodium hydroxide solution J vcj 50 ml) is stirred 2 5 i psi amid azat Filgruck Gy product washed with an acid jar 10 j after drying yu 50 ° C g s si fluoro-1-methyl 3-methythio 4 l /) -, 3; th 164.5-165 5 ° C (1 55 g)
    Example 8 Rasteor sodeoh 1- (4-fluoro-2-methylaminophenyl) -2 finylethanone (161 0 g) psigo-sp r similar to the method of san p i - pel in acetic acid and p7 ml u Lcf mixed with smeg, / and Cyclic acid pack (228 2 g) acetic acid brush 21 C m / la (392 ml at 83 C in, e Reaction mixture of omean / 80 ° Sesche2ch then pstepne-n. to temperature oKpyAdiom, eii L, distilled filtrates filtration and pjOvtis HH with dichloromethane (400 ml) KO-URN l. by distillation until the filter w / leg-1 was added.that the mixture did not reach n-st 132 ° g o was cooled to the temperature from the medium. vi shuffle 10 min / layers separated; A water phase with an additional amount of g (2 x 200 ml) organic g t is ny, then washed oh - i m sodium hydroxide (5 M 200 vn)} and in vacuum When it is e in nc, iu i 74 ° С 0 4 mm Hg C) i, fluorine-2 - (melamino gsch v. Tr 53 ° С
    The mixture consists of j Read (63 ml) and formic acid / g- mix and mix j-g nitrogen atmosphere for 2 hours g — Jd bath with ice and s-i / 0, i in portions for 30 min. 4 iJ - lamicho) acetophenone (529 - 1 g 1dG
    The mixture is filtered, and the residue is washed with technical denatured alcohol (100 ml). The filtrate and denatured washes are combined and a little brown oil is obtained by evaporation. This brown oil is stirred with hydrochloric acid (5 M 2 2 5 h and then dichloromethane (600 ml) is added The layers are separated and the aqueous phase is further extracted with dichloromethane (2 x 30 ml). The organic layers are combined and, after evaporation, I get 1 4-fluoro-2 - (methylamino) ace ofenon B as a brown oil which is squirted at ambient temperature.
    The mixture consisting of acetic anhydride (92 ml) and pyric acid k62 7 ml} is stirred and stirred for 2-5 hours under nitrogen and then cooled to ambient temperature. for 30 min at temperatuoe chchhe ZESS part prsd / GTC ass jeinogo s po least 8 (77 1 g) The reaction is stirred etc. ambient temperature 21 hours and then cooled in an ice sape salt alternately then adjusting w g zsdu (320 ml) and an aqueous solution of idosyuk / c / i sodium (specific gravity 1 5 180 mp) potsder za temperature nor / ce ZS ° C pog at 1C-I n / a mixture ekstsagirlsg, ii -loometch C | - / (Sx 125 -inj and obetsinenye5 .rektg stand at 0 ° C under nitrogen agmosLeoe in -ls- overnight s
    A solution of za-ON jnea dichloome in a nitrogen atmosphere and ice / bath with salt and why was it added a solution of sulfuryl chloride (81 7 ml) in dichloromethane (110 ml) for 35 mi at a temperature below 0 ° C. After stirring for 1 75 h, the mixture is diluted with water (280 ml) for 25 minutes while maintaining the temperature below 25 ° C. The resulting layers are then separated and the organic layer is cooled in an ice bath with salt in an atmosphere of nitrogen. Then it is added dropwise s for 70 minutes a solution of methane-olata chatr / s methanol (2 55 M 388 ml) The mixture is gradually heated up to ambient temperature the food is stirred for 1.5 hours; acidified with hydrochloric acid (5 M, 100 ml) and kept overnight
    Zodiac is added (200 w, the resulting layers are separated. The aqueous phase is extoted with an additional amount of luchlormethan (70 ml) and the organic layers are combined. The solvent is removed from the combined organic (distillation) by distillation and progress of the distillation of petroleum ether (t un 10 -120 ° C 300 ml) The distillation is continued until the cooled mixture reaches a temperature of 100 ° C. The mixture is cooled to 20 ° C and filtered and the residue is washed with a mixture of ether (t 102-120 C, 2 ° C Nifl After drying the precipitate at 50 ° C
    vacuum, an orange-yellow Veg Do1I 7 9 g is obtained. After crystallization of a sample of the product 0 38 O-tech, four C (denatured alcohol) (3.5 ml), 7-fluoro-1n ml-3- (methylthio) -4-hins is obtained pl 162-1b31S
    iO 26,)
    Example 1C p-thief containing 3-chlorophenolic acid - (3.49 g) in dichloromethane (80 ml) was added to a stirred solution of 1- (4-fluoro-2-ethyl-aminophenium} -2- (methylthio) zgnola ( 43 g) gr prepared in dihgorm ano (75 ml) under nitrogen atmosphere for 15 minutes maintaining the reaction temperature below 26 ° C. Reactionary reaction: keep stirring for another 2 hours at temperature: dry medium. Then, saturatively grower, bicarbonate-sodium v after vri-riviznich in vac / vvie get solid.; pro When rice zlp / zaii from ethanol
    receive 1- (4-fluoro-2-methyl-amigum ofenyl; -2-methylsu / phenyl / ethanone t mp, 3 -138CC
    Hepagetus1 ches -.v OK g vnostpe ppe r; laga-r IA connections and promester 1
    SPS / SUSH | / 1M ISGI1TZGN, F. 1 SO MI
    randomized administration of comp. not 1- / 1 OULP go with l- | acchg shpsikzionno ion
    The specified test was carried out according to the method of metsd 1x
    In the test isz zizli weight
    130-240 g of Brypha from xyx with spontaneously arising hypertension Aok Ckamoto Kpoic four for each i-v test myl group prepared food in .e but / before administering the test compound (act / ark dose of formula I 30)
    权利要求:
    Claims (1)
    [1]
    Formula izobrs e n and Method of obtaining hiyogotsyvogo pooiz NATIVE phoomgir |
    Sch
    3
    xx s
    N
    I
    what does it mean with purpose
    increase in the yield of the target npoflv Ta soschelS | B- south for1-, Russia: no connections
    FJD formulas:
    ABOUT
    sen
    NHCH,
    h le / with o j i i, „t i / r., i j i e e coste pei-vA rS JCMCsa i e
    COt i FOOLL G ,,
    ; i
     f - - Y A
    XR - l-N-MC
    G 11
    -P-,
     / i guluchennoe soedmne. from no / i & p d t ai i to a detstviyu with isa otdiruyusch1 | M agent tchlym like chloris and LV nbq voM / 1 e egane at his tempoaguage nih c ° r with ob (: for chtoza1-IRM com / nechi / - i-i
    g g and s
    V- - /
    .
    x-, h but
    1 a -iMi.
    2 Л01 / and i - | j
    i / psp chenpoi / ipoz. r j j D i g action with cer -, / .. i. HVI e (nlг0z, in the form of ol ani tg i with them as a legan ./idle. I create i eat as much as jrc as a mixture of a / c n-methanol npi tag / paratur OS a-CLd i / er / e
    E f
    .C -,
    / | L "i / i LETSIZ1 / POL IJ8
    1 P1 i with ai / c-scsg
    1C i h o L
    rtri B with re with TR
    -f d o Wed
    jdi / er er vp
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    FI893405A0|1989-07-13|
    DE3866086D1|1991-12-12|
    PT89024A|1988-12-01|
    PL275880A1|1989-06-12|
    WO1989004827A1|1989-06-01|
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    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
    GB878726950A|GB8726950D0|1987-11-18|1987-11-18|Chemical process|LTRP1011A| LT2519B|1987-11-18|1993-09-20|THE CHINOLON DENTAL RECEIVING BUDGET|
    LV931270A| LV5671A3|1987-11-18|1993-11-25|Satisfaction of the acquisition of quinolone derivatives|
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