• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
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  • 引用文献
  • 法律状态
  • 优先权
    • 专利摘要:
    Certain thiazolinyl or thiazinyl benzimidazole ester compounds are useful as antiviral agents.
    公开号:SU721003A3
    申请号:SU762390302
    申请日:1976-08-26
    公开日:1980-03-05
    发明作者:Говард Вайкл Джеймс；Джонсон Пэйджет Чарльз
    申请人:Эли Лилли Энд Компани (Фирма)；
    IPC主号:
    专利说明:

    (54) METHOD FOR OBTAINING DERIVATIVES OF TIAZOLINILILI TIAZYNYLBENZIMIDAZOLE
    721003 compounds of the formula (D), where R is formyl or C (OJRgf where Rj has the above values. On treatment, a benzimidazole of formula (P) with sodium hydride or methyl TSH aryyTGLY-AidIy1 potassium, or tert-butylate potassium is formed as an hydrate One of the nitrogen atoms which, upon further interaction with the haloalkyl isothiocyanate of formula (} |), forms a mixture of 5- and 6-isomeric compounds in connection with the known isomerism of benzimidazole compounds. According to the invention, the base is taken in a small beat by the benymidazole and the base. The ratio is ill-1g2. The molar ratio between benzimnzazole frmula (C) and yyDIsyl isothiocyanosanate can vary from 1: 1 to 1: 1, 5; Target compounds can be separated by conventional methods, such as filtration and subsequent concentration of the filtrate to the beginning crystallization / For removal of essential products, it can also be used in a solvent, such as acetone or methanol. The solution after the filters is concentrated and the crystallization of the Sch m of a suitable solvent ..., 5 (6) -isomers, which are formed as a result of the interaction of the compound of formula (p) with haloalkylism with a thiocyanate of formula (t), can be {separated by fractional crystallization or chromatography column. Usually, the b-isomer crystallizes from a solution of a mixture of isomers. The structure of the isomers can be determined by signals in the 7.0-8.3m region of the PMR spectrum. Compounds of formula (I), where R formyl or C (, can be obtained by acylation of a compound of formula (I), where R is hydrogen, anhydride with acetic, propionic or MBC, lnry acid or a mixture of anhydrides of muravine and acetic, propionic or butyric acid.
    , S S-Jr;: S: ..- .. i.N; Example 1, 1-Thiazolinyl- (thiazinyl) -2-amino-5 (6) -ethoxycarbonylbenzimidazoles (general procedure). , 54 g (0.265 mol) of 2-amino-5 (6) -ethoxycarbonylb, enzimidazole are suspended in LOO ml of ethylene glycol dimethyl ether (dimethoxyethane, DME). Then, with stirring, 13 g (O, 27, mol) of sodium hydride are added in the form of a 50%, -. Suspension in mineral oil. Next, a solution of 33 g (0.27 mol). p-chlorostilisothiocyanate in 50 ml of dimethoxyethane is added dropwise to the resulting reaction mixture, kept in ice-cold lehane to lower the temperature, of the exothermic reaction. After that, the reaction mass is stirred at night at an OM temperature. The precipitated product is filtered and washed with a sufficient amount of ethylene glycol dimethyl ether, water, and ether. After drying, the yield of the mixture of isomers was -. em 52 g (67.5%). This product is dissolved in 2 lab absolute alcohol and filtered. The filtrate is concentrated and the isomeric products are separated by fractional crystallization. Yield 1- (thiazolin-2-yl) -2-amino-5-ethoxy-carbonylbenzimidazole 12 g m.p. 218-220 ° C. The yield of 1- (thiazolin-2-yl) -2-amino-6-ethoxycarbonylbenzimidazole is 22.4 g, so pl. 189191 ° C. Found,%: dl. 5-isomer: C 53.85; H 5.02; - N 19.07 for the 6-isomer:. C 53.62; H 4.64; N 19.07, C, j H ,, .S. Calculated,%: C, 53.78; —H, 4.86; -. N19.30. 1- (Thiazolin-2-yl) -2-amino-6-ethoxycarbonylbenzimidazole is also obtained using the bases and solvents shown in the table. The yields listed in the table were obtained using 1 g (0.0049 mol) of 2-amino-5 (6) -ethoxycarbonylbenzimidazole and 650 mg (0.0053 mol) (b-chloroethyl isothiocyanate,
    ) scft. Sodium hydride (50% dispersion) Methyl sodium Amide sodium tert-Butylate potassium Toluene is distilled off in vacuum, the residue is rolled in 300 ml of water,. , Example 2. Using the method of Example 1, 1- (4-methylthiaz al-2-and -2-amino-5 (6) -ethoxycarbyl benzene, midazol is obtained as an isomeric mixture of 5, 5 g (52%) of .7.2 g (0.035 mol) of 2-amino-5 (6) -e sicarbonylbenzimidazole and 2-chloro-1-methyl ethylisothiocyanate, t, mp, 183-190 (192-210) ° C. Found,%: C 55.4V; H 5.14; N 18.81, tt ,,, S. Calculated,%: C 55.26; H 5.26; N18.42, Example 3, In terms of pr measure 1 1- (5-methylthiazolin-2-yl) -amino-5 (6) -ethoxycarbonylbenzim azole is obtained in the form of an isomeric mixture in an amount of 4, 5 g (4.2%) of 7.2 g (0.035 mol) 2-amino-5 (6) -ethoxycarbonylbenzimidazole and 2-chloropropylisothiocyanate , t, pl 155-158 (J79-186) ° C. Found,% ..: C 55.06; -H 5.22 ;. N18.16, C 11.4 S Calculated,%: C 55, 26; H 5.26; N 1B, 42. Tetragues furan Toluene Tetragi furak Dimetok ethane Toluene Tetragi irofuran Toluene Dimetok ethane, 3 (93) White solid, 74 (53) 9 (56) Tan tan solid, 68 ( 49) Orange solid, 58 (41) White solid, 81 (58) Light orange solid, 22 (87) Orange solid, 70 (50) Yellow solid while still mixed with methanol and poured. Example 4. Under the conditions of Example 1, 1- (4,5-dimethylthiazolin--2-yl) -2-amino-5 (6) -ethoxycarbonylbenzimide. Ash is obtained as an isomeric mixture in the amount of 2.2 g from 7.2 g of 2-amino-5 (6) -ethoxycarbonylbenzi 4idazole and 3-chloro-2-isothiocyanbutane, mp 24-138 (151-155) ° C. Found,%; C, 56.45; Nb, 11; N 17.54, H, 8 N, 0, S. Calculated: С Н 5,66; N 17.61. Example 5. Under the conditions of Example 1, 1- (thiazin-2-yl) -2-amino-5 (6) -ethoxycarbonylbenzimidazole is prepared from 7.2 g (0.035 mol) of 2-amino-5 (6) -ethoxycarbonylbenzimidazole and C -chloropropylisothiocyanate. The isomers are separated by fractional crystallization from ethyl acetate. Found,%: 5-isomer: C 55.40; H 5.16; N 18.19. 6-isomer: C 55.02; H 5.23; N 18.13. С -.- Hi6, Calculated,% s С 55,25; H 5.30, -Y 18., 41 .. Output of the 5-isomer 0.9 g, m.p..l57lbO c, output of the b-isomer 2.3 g, m.p. 163-166 C. Example 6. 1 - (ThiaEOlin-2-yl) -2-amino-b- (1-imidazolylcarboxylic), obtained from 1- (thiazolin-2-yl) -2-amino-b-benzimidazolecarboxylic acid and 1,1-carbonylbisimidazole, 1.3 g (4.2 m of 1- (thiazolin-2-yl) -2-amino-6- (1 - ,, .. -Imidazolylcarbonyl) -benzimidazole iB 25 MP of methanol and 15 ml of dimethylphosphamide are heated on water In the d-f% 5c rtoi5 bath, Tioka, the solution is not stanon homogeneous. BATTERY BATTERY evaporated b: in BaKVyMe Yosuh, water is added to the residue and the undissolved product is filtered. 1- (thiazolin-2-yl) -2-amino-5 (6) -methoxycarbonylbenzimidazole mp 209-211 ° C, Found,%: C 51.99; H 4.16; N 20.08. C , g H „YdO, Z. Mol. weight 276. C 52.16; H 4.38; Calculated,% N 20.28. 7. A. Cyclohexyl Example -3-nitro-4-chlorobenzoate .10 g (0, 05 mol) 3-nitro-4-chlorobenzoic acid, 50 ml of benzene, 13 g (0.1 mol) of oxyalyl chloride and 3 drops of pyridine are stirred at room temperature for I h. The mixture is heated at 55 ° C to obtain a homogeneous solution. The reaction mass is evaporated in vacuo and 12 g of 3-nitro-4-chlorobenzoyl chloride are obtained. 12 g of (0,) 3-nitro-4-chloro-benzo-ochloride is dissolved in 290 ml of benzene and then 8 ml of pyridine are added. After this, a solution of 5 ml of cyclohexano is added to this mixture. la in 50 ml of benzene. The resulting mass was boiled for 4 hours and filtered. The benzene filtrate is thoroughly washed with dilute acid, dilute alkali and water. The benzene solution is dried and evaporated in vacuo. 12.5 g (88%) of cyclohexyl-3-nitro-4-chlorobenzoate are obtained, mp: 57-58 ° C. Found,%: C 54.90; H 5.15; N 5.14. C, C H C1NO4 .. Calculated,%: C 55.04; H 4.97; N 4.94 .. B. Cyclohexyl-3-nitro-4-dibenzylaminobenzoate. A mixture of 2.8 g (0.01 mol) of cyclohex sil-3-nitro-4-chlorobenzoate and 4.4 ml (0.022 mol) of dibenzylamine in 20 ml of dimethylformamide is boiled for an hour. Then the first mass is evaporated in a vacuum and the residue diluted with 500 ml of water. The aqueous mixture is extracted with ethyl acetate, the cSTiiaT ethyl acetate solution and evaporated in vacuo. The residue is taken up in ether and filtered. The solution is evaporated in vacuo to give 4.2 g (95%) of cyclohexyl 3-nitro-4-dibenzylaminobenzoate as an oil. B. 2-AMINO-5 (6) -cyclohexyloxycarbonylbenzyme dazole, 100 g (0.386 mol) of cyclohexyl-3-nitro-4-dibenzylaminobenzoate is hydrogenated at 60 ° C for 22 h in the presence of 25 g of palladium deposited on activated carbon in 875 ml of absolute ethanol. The catalyst is filtered off and the filtrate is evaporated in vacuo. The residue after evaporation is dissolved in ethyl acetate and filtered. Anhydrous gaseous hydrogen chloride is passed into the ethyl acetate solution with stirring. The precipitated o-phenylenediamine hydrochloride salt is collected and washed with dry ether. 24.3 g of product are obtained. This salt was dissolved in water and the pH of the solution was adjusted to 7.0 by adding 1N sodium hydroxide solution (130 ml). Then to this solution. 40 ml of methanol and 9 g (0.0845 mol) of cyanogen bromide are added, and the resulting reaction mixture is stirred overnight. The aqueous mixture is then neutralized with 1N sodium hydroxide solution and extracted with ethyl acetate. The ethyl acetate extract is decoloured with charcoal and filtered. The ethyl acetate solution is evaporated in vacuo to give 16 g (73%, yield based on cyan bromide) of 2-amino-5 (6) -cyclohexyloxycarbonylbenzimyl alcohol as an oil. G. 1- (Thiazolin-2-yl) -2-amino-6-cyclohexyloxycarbonylbenzimide-azole. Out of 7.8 g (0.03 mol) of 2-amino-5 (6) -cyclohexyloxycarbonylbeneimidol, 100 ml of dimethoxyethane (glyme), 1.5 g of sodium hydride suspension in the form of a 50% suspension in mineral oil and 3.7 g (0.03 mol) i-chloroethyl isothiocyanate under the conditions of Example 1 gives 1.2 g of 1- (thiaz-al-2-yl) -2-amino-6-cyclohexyloxycarbonylbenzimidazole, m.p. 231-232 C (meth-C 59 , 06; H 5.72; Found,%: N 16.47. C ,, H ,,, N, 0, S. Calculated,%: C 59.28; H 5.85; N 16.27. Example 8. 1- (Thiazolin-2-yl) -2-amino-5 (6) -isopropyloxycarbonylbeneimidazole is obtained from 2-amino-5 (6) -isopropyloxycarbonylbenzimidazole, which in its turn prepares from isopropyl-3-nitro-4-chlorobenzoate; under conditions of example 7. 6.6 g (0.03 mol) of the above, benzimidazole, 100 ml of dimethoxyethane, 1.5 g of 50% suspension of sodium hydride and 3, 7 g of p-hl ethyl eothiocyanate of psdzwergaMt wey and receive 3 g of 1- (thiazole -2-yl) -2-amino-5 (6) -isopropylcarbonylbenzimidazole, mp.196205 0. Found% C 55.05; H 5.23 N 18.37, C, H ,, S. - Calculated,%; C 55.25; H 5.30; N 18.41. PRI me R. 9. 1- (Thiazolin-2-yl) -2-amino-b-neopentyloxycar bonylbenzimidazole is obtained by charging with 9.9 g (40 mol) of 2-amino-5 (6) -neopentyloxycarbonylbenzimidazole (via neopentyl-3-nitro-4 -chlorobenzoate), 2.0 g of a 50% hydride suspension, 200 ml of dimethoxyethane and 4.9 g of p-chloroethane isothiocyanate under the conditions of the example. The yield of the 6-isomer is 1.54 g, m.p. 236 238С (decomp.). Found,%: C 57.75; H 5.85; N 16.82. Ci5. Calculated,%: C 57.83; H 6.02; . N 16.86. Example 10. A. tert-Butyl-3,4-dinitrobenzoate. . 53 g (0.25 mol) of 3,4-dinitrobenzoic acid, 500 ml of benzene, 65 g (0.51 mol) of oxalyl chloride, and 1 ml of pyridine are treated under the conditions of example 7 A. 3,4-dinitrobenzoyl chloride is obtained in the form of an oil-like product. This product in 500 ml of benzene, 25 ml of pyridine and 22 g (0.3 mol) of tert-butyl alcohol is treated under the conditions of Example 7A and 33 g (49%) of tert-butyl-3,4- is obtained. din robenzoat. Found,%: C 48.95; H 4.30; N 10.14. C ,, N ,,. Calculated,%: C 49.26; H 4.51; N 10.44. B. 2-amino-5 (.6) -t-butyloxy carbonylbenzimidazole. 4.2 g (0.02 mol) of tert-butyl-3, 4-dinitrobenzoate are hydrogenated in 95 ml of ethanol in the presence of 1 g of 5% palladium supported on activated carbon for 1 hour at room temperature. As a result of the exothermic reaction, the temperature rises to 45 ° C. Hydrogen uptake is 85% of theory. The catalyst is filtered off and the filtrate is evaporated in a vacuum to dryness. The residue of tert.-butyl-3, 4-diaminobenzoate in an amount of 0.017 mol is introduced into a mixture of 20 ml of methanol and 200 ml of water. 1.8 g (0.017 mol) of cyan bromine is added to this mixture and then the process is carried out according to the procedure described in procedure 7 V. 1.5 g (38%) of 2-amino-5 (6) -t-1 is obtained. butyloxycarbonylbenzimidazole. 28 g (0.1 mol) of 1-cyclopropylethyl-3, 4-dinitrobenzoate are hydrogenated in 700 ml of ethanol in the presence of 3 g of 5% palladium, applied on activated carbon, for 1 hour at room temperature. As a result of the exothermic reaction, the temperature reaches 45 ° C while absorbing hydrogen, which is 100% of theory. The catalyst is filtered off and the filtrate is evaporated in vacuo. The oily product is l-cyclopropylethyl-3, 4-diaminobenzoate vas-. d to 600 ml of water and 60 ml of methanol, 10.4 g of bromine cyanine are added to the mixture, and then treated as described for Example 7 C. 18.6 g, (76%) of 2-amino-5 (6) - (1-cyclopropylethoxycarbonyl) -benzimidazole as an oil, which soon solidifies. B. 1- (Thiazolin-2-yl) -2-amino-5 (6) - (1-cyclopropylethoxycarbonyl) benzimidazole. .. 7.8 g (0.03 mol) 2-a: mino-5 (6) - (1-cyclopropylethoxycarbonyl) -benzimidazole, 100 ml of dimethoxyethane, 1.5 g of 50% sodium hydride1, and 3.7 g (0.03 mol) f, -chloroethyl isothiocyanate is treated as in Example 1. 1- (thiazolin-2-yl) -2-amino-6- (1-cyclopropylethoxycarbonyl) -beneimidazole is obtained, m.p. 185-189 p. Example 12. A. i-Phenylethyl-3, 4-dinitrobenzoate. 53 g (0.25 mol) of 3,4-dinitrobenzoic acid, 500 ml of benzene, 65 g (0.5 mol) of oxalyl chloride and 1 ml of pyridine are treated as in Example 7 A to give oily 3,4-dinitrobenzoyl chloride. B. 1- (Thiazolin-2-yl) -2-amino-6-tert.-butyloxycarbonylbenzimidazole, 3 g (13 mol) 2-amino-5 (b) -t-butyloxycarbonylbenzimidazole, 100 ml dimethoxyethane, 0.7 g. 50% sodium hydride slurry and 1.8 g | The chloro-isothiocyanate is treated under the conditions of Example 1. 300 mg of the 6-isomer are obtained, i.e. 1- (thiazolin-2-yl) -2-amino-6-tert.-butyloxycarbonylbenzimidazole, m.p. 218219 ° C. Found,%:. C 56.80; H 5.92; N 17.61. - H, in, Calculated,%: C 56,58; H 5.70; N 17.60. Example 11. A. 1-Cyclopropylethyl-3, 4-dinitrobenzoate. 53 g (0.25 mol) of 3,4-dinitrobenzoic acid, 450 ml of benzene, 65 g (0.5 mol) of oxalyl chloride and 1 ml of pyridine are treated under the conditions of Example 7 A. A 3,4-dinitrobenzoyl chloride is obtained.
    权利要求:
    Claims (1)
    [1]
    Claim
    The method of obtaining derivatives of 'thiazolinyl total
    - or thiazinylbenzimidazole— of the formula (I)
    NHR where
    R <30 with ethyl acetate and concentrated in vacuo, and then crystallized from ethyl acetate. 700 mg of 1- (thiazolin-2-yl) -2-formamido-5 (6) -ethoxycarbonylbenzimidazole are obtained, m.p. 179-184 (201-208) ° C.
    Found,%: C 52.78; H 4.73;
    N, 17.72.
    SD4 I-14 O3 S
    Calculated,%: C 52.82; H 4.43;
    N, 17.60. Example 14, 1- (5-Methylthiaolin-2-yl) -2-amino-5 (b) ethoxy R z hydrogen, formyl or the group CfOJR ^;
    C, -C 6 -alkyl, C 3 -C 7 -cycloalkyl, (Cj-Cy-cycloalkyl) -B g or phenyl; C, -Cj-alkyl;
    the group R, O (O) C xa in the position η = 2 or 3; w = or 2, and s and y with s I find 5 or 6; 0 or 1, the compound of the general formula * has the above indicated that they interact with the fact that,
    X - (( N g ) l - NCS g where the type are the above values, and X is chlorine or bromine, in the presence of sodium hydride or sodium methylate, or potassium amide, or tert:; potassium butylate in dimethoxyethane or tetrahydrofuran, or toluene, followed by isolation of the target product of formula (I), where R is hydrogen, or acylation to obtain the compound of formula (I), where R is formyl or C (O) R 2 .
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    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    US3749717A|1971-05-04|1973-07-31|Squibb & Sons Inc|Thiazolinyl and thiazinyl derivatives of benzimidazoles|
    US3825537A|1972-02-28|1974-07-23|Squibb & Sons Inc|1-thiazolin-2-yl-2-aminobenzimidazoles and derivatives thereof|
    US3833574A|1972-07-31|1974-09-03|Squibb & Sons Inc|Benzimidazolinone compounds|CA1076582A|1975-10-28|1980-04-29|Charles J. Paget|Antiviral thiazolinyl or thiazinyl ketobenzimidazoles|
    US4293558A|1975-10-28|1981-10-06|Eli Lilly And Company|Antiviral thiazolinyl benzimidazoles and derivatives|
    US4338315A|1979-11-14|1982-07-06|Eli Lilly And Company|Antiviral method employing thiazinyl benzimidazole derivatives|
    US4191832A|1979-03-12|1980-03-04|Eli Lilly And Company|Separation of syn and anti oximes of 1-sulfonyl-2-aminobenzimidazoles|
    US4401817A|1981-04-20|1983-08-30|Eli Lilly And Company|Carbonyl-substituted 1-sulfonylbenzimidazoles|
    US4463181A|1982-04-08|1984-07-31|Eli Lilly And Company|Process for removing sulfonyl groups from benzimidazole isomers|
    US4434288A|1982-04-08|1984-02-28|Eli Lilly And Company|Preparation of substituted 1-thiazinyl or 1-thiazolyl-2-aminobenzimidazoles|
    IL68297A|1982-04-08|1986-09-30|Lilly Co Eli|Process for removing 1-sulfonyl groups from 2-amino-5-substituted benzimidazoles|
    US4420479A|1982-04-08|1983-12-13|Eli Lilly And Company|Olefinic benzimidazoles, formulations, and antiviral methods|
    US4492708A|1982-09-27|1985-01-08|Eli Lilly And Company|Antiviral benzimidazoles|
    US5508594A|1994-06-10|1996-04-16|Westinghouse Electric Corp|Electric vehicle chassis controller|
    US6358971B1|1998-05-20|2002-03-19|Eli Lilly And Company|Anti-viral compounds|
    US7649007B2|2006-08-15|2010-01-19|Wyeth Llc|Oxazolidine derivatives as PR modulators|
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    TW200815428A|2006-08-15|2008-04-01|Wyeth Corp|Oxazolidone derivatives as PR modulators|
    US7538107B2|2006-08-15|2009-05-26|Wyeth|Oxazinan-2-one derivatives useful as PR modulators|
    US20080045560A1|2006-08-15|2008-02-21|Wyeth|Pyrrolidine and related derivatives useful as PR modulators|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    US05/633,203|US4008243A|1975-11-19|1975-11-19|Antiviral thiazolinyl or thiazinyl benzimidazole esters|
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