• 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:
    6-Substituted-1,2-benzisothiazolin-3-ones carrying an aminoalkyl group in the 2-position and being optionally substituted in the 4- and/or 5-position are antithrombotic agents. The compounds, of which 2-(2-diethylaminoethyl)-4,5-dimethyl-1,2-benzisothiazolin-3-one is a representative embodiment, can be prepared by cyclization of an appropriately substituted bis-[2-(aminoalkylcarbamyl)phenyl]disulfide, or by other disclosed methods.
    公开号:SU820661A3
    申请号:SU772444406
    申请日:1977-01-20
    公开日:1981-04-07
    发明作者:Бейзхаген Хорст；Хейрлайн Ульрих；Хайде Фрида Мэнг Ильзе；Сойтер Фридель
    申请人:Байер Аг (Фирма)；
    IPC主号:
    专利说明:

    1,2-BENZYZOTHIAZOLINON-3. ; bimiamide diphenyl disulfide-2,2-dicarboxylic acid of the general formula TI / A CONH-AN (I si NA-NHCO in which R - R and A have the indicated meanings, is subjected to oxidative cyclization. Oxidative cyclization can be carried out, for example, chlorine, bromine or thionyl chloride The reaction is preferably carried out in an inert organic solvent at 10-100 ° C, especially at 20-80 ° C. The duration of the reaction depends on the decomposition temperature and is 1-24 hours. As inert solvents, it is preferable to take halohydrocarbons, especially such as tetra lung carbon, chloroform or methylene chloride .. If thionyl chloride is used as the oxidizing agent, it is preferably operated with an excess of three to five times the amount. If it is chlorine or bromine used as an oxidizing agent, then preferably equivalent amounts are taken. The reaction can be carried out at normal pressure, but also at elevated. They are usually operated at normal pressure. If 5,3-M- (2-diethylamino) -ethylamide 3,3,5,5-tetramethyldiphenyl disulfide-2, 2-dicarboxylic acid is taken as the starting compound and Thionyl Chloe Id, the reaction proceeds according mc follows. The following scheme is COHHtHgdHgNCj J5 (HS CgHs g $ 0 (la ctsHgSHgNoCo CgHs, ", Kjf4 Amides of diphenyl disulfide-2.2-biscarboxylic acid of formula (IG) are also new. They can be obtained by known methods, if the corresponding 2-syndicates, I-yrs) are available. Diphenyl disulfide-2 2-biscarboxylic acid is converted with SOCf and then chl RID in an ethanol solution is reacted with the corresponding basic amines. Example 1. Preparation of 2- (3-dimethylaminopropyl) -6-xLoro-1,2-benzisothiazolinone-3 22 g of bis-N- (3-dimethylamino) -propylamide 5,5-di Lord of the diphenyl disulfide-2, 2-dicarboxylic acid dihydrochloride is dissolved in 50 ml of chloroform and 50 ml of thionyl chloride is slowly added dropwise. The mixture is kept for 18 hours at 35-40 ° C and then evaporated in vacuum. The residue is taken up in 100 ml of water, the insoluble parts are removed, the aqueous the solution is alkalinized by adding sodium hydroxide and the precipitated base is extracted several times with ether. The ether extract is dried and evaporated. After recrystallization, 15.1 g of 2- (3-dimethylaminopropyl) -6-chloro-1,2-benzisothiazolinone-3 are obtained in the form of colorless plates m.p. 69 ° C, yield 78%. The corresponding hydrochloride is obtained by adding ethanolic hydrochloric acid as colorless prisms that are recrystallized from ethanol, m.p. 208 ° C. The starting compounds can be prepared as follows. a) Preparation of 5,5-dichlorodiphenyl disulfide-2, 2-dicarboxylic acid chloride. 15.4 g of 4-chloro-2-mercaptobenzoic acid are fed into 45 ml of thionyl chloride and the solution is stirred for 5 hours at 60 ° C. Excess thionyl chloride is then removed in vacuo. The crystalline residue after recrystallization from benzene has so pl. 184c, yield 12.6 g, 75% of theory. b) Bis-N- (3-dimethylamino) -propylamide 5,5-dichl-rdiphenyl disulfide-2, 2-dicarboxylic acid dihydrochloride, 20.6 g of 5,5-dichlorodiphenyl disulfide-2 chloride, 2 dicarboxylic acid are dissolved in 100 ml of tetrahydrofuran and at room temperature, the mixture is added dropwise to a solution of 5.1 g of 3-dimethylaminopropylamine in 100 ml of ethanol. Stir for another 2 hours and condense the reaction solution in vacuo. The formed syrup slowly crystallizes. The crude product can be cyclized without further purification. After conversion from ethanol, the compound has a mp. decomposition). Exit 35% of theory. Analogously to Example 1, the compounds of Examples 2-31 are prepared. Example 2. 2- {2-Diethylamino-ethyl-6-chloro-1, 2-benzisothiazolinone-3. Prepared from bis (2-diethylamino) ethylamide) 5,5-dichlorodiphenyl disulfide-2, 2-dicarboxylic acid. Colorless cyclohexane prisms, i.e. , yield 65% of theory. Hydrochloride - colorless cone crystals from ethanol, so pl. 210 yield 90% of theory. Example .3. 2- (4-Diethylamino -1-methyl) -butyl-6 chlorine-1, 2-benzisothiazolinone-3. Prepared from bis-M- (4-diethylamino-1-methyl) -butylamide 5,5-dichlorodiphenyldisulfide-2, 2-dicarboxylic acid. Yellow syrup. H-NMR (60 MHz, in TMS): CH3 8.95 (t, 6H) ,. CH3 8.55 (d, ZN) N-CHe - 7.45 (KB, bN), -CHgCH - 8.3 (m, 4H), hetero-N-CH- 5.10 (sextet 1H) aromatic. protons 4-H 2.0 (d), 5-H 2,6 (d), 7-H 2.35 (s). Yield 26 of the theory .. Example 4. (2-Dimethylaminoethyloxy) 7-ethyl-6-chloro-1,2-ben isothiazolinone-3. Prepared from bis-Y-2- (2-dimethylaminoethyloxy) ethylamide 5,5-dichlorodiphenidtsisulfide-2, 2-dicarboxylic acid. Salt 1/2 1,5-naphthalindisulfonic acid - colorless przyl.il from water, so pl. 259-260 0, yield 18% of theory. Example 5. 2- (4-Diethylamino-1-methyl) -butyl-6-methoxy-1,2-ben isothiazolinone-3. Salt 1/2 1,5-naphthalindisulfoxys lots - colorless prism from water, so pl. 218 ° C, yield 25% of theory. Example 6. 2- (3-Dimethylamine | But) -propyl-6-methoxy-1,2-benzisothia 1zolinone-3. 1. Bis-N- (3-dimethylamine propylamide 5,5-dimethoxydiphenyl sulfide-2,2-dicarboxylic acid) is obtained. Salt 1/2 1,5-naphthalene disulfoxide - colorless prisms from ethanol (with the addition of a small amount in dy) , m.p., yield of 31.5% of theory. Example 7. 2- (3-Diethylamino-propyl-6-methoxy-1,2-benzisothiazolium non-3. Semigiot from bis-M- (3-diethylamino propyl amide 5, 5-dimethoxydiphenyl sulfide-2,2-dicarboxylic acid. 1/2 salt of 1,5-naphthalene disulfonic acid from a mixture of methanol and acetone, colorless crystals, mp 228-229 ° C, yield 15% of theory. Example 8. (2 -Dimethyl-aminoethyloxy) D-ethyl-6th etoxy-1,2ibenzisothiazolinone-3 .. Prepared from bis-N-2- (2-dimethylaminoethyloxy) ethylamide 5,5-dime-oxydiphenyl disulfide-2,2-dicarboxylic acid. Oxalic acid salt - free colored crystals, so pl. 137-138 ° C, yield 9% of theory. PRIOR LER 9. 2- (3-Diegylamino) -propyl-5,6-dimethoxy-1,2-benzisothiazolinone-3. Prepared from bis-N- ( 3-dstilamino) propylamide 4,5,4,5-tetramethoxydiphenyl disulfide-2, 2-dicarboxylic acid. Salt of oxalic acid - colorless crystals, so pl. 138-140s, yield 13% of theory. Example 10. 2- (2-Diethylamino) -ethyl-5, b-dimethoxy, 2-benzisothiazolinone-3. Prepared from bis-N- (2-diethylamino) -ethylamide 4,5, 4, 5-tetramethoxydiphenyl disulfide-2, 2 dicarboxylic acid. Salt 1/2 1,5-naphthalindisulfonic - colorless crystals, so pl. 234-235 0, yield 31% of theory. Example 11. 2-p- (Diethylaminoethyloxy) | -ethyl-6-chloro-1,2-benzisothiazolinone. Prepared from bis-M- 2- (2-diethylaminoethyloxy) ethylamide 5,5-dichlorodiphenylsulfide-2, 2-dicarboxylic acid. Yellow oil, yield 24% of theory. Example 12. 2- (2-Diethylamino) -ethyl-6-ETOXI-1,2-benzisothiazolinone-3. Prepared from bis-N- (2-diethylamino) -ethylamide 5,5-diethoxydiphenyl disulfide-2, 2-dicarboxylic acid. Colorless prisms of methanol, so pl. , yield 23% of theory. Example 13. 2- (3-Dimethylamino) -propyl-6-ethoxy-1,2-benisothiazolinone-3. Prepared from bis-N- (3-dimethylamino) -propylamide 5,5-diethoxydiphenylsulfide-2, 2-dicarboxylic acid. Salt 1/2 1,5-naphthalindisulfonic - colorless prisms from ethanol with the addition of a small amount of water, so pl. , yield 35% of theory. . Example 14. 2- (3-Dietylamino) -propyl-b-ethoxy-1,2-benzisothiazolinone-3. Prepared from bis-N- (3-diethylamino) -propyl-5, 5-diethoxydiphenyl disulfide-2, 2-dicarboxylic acid. 1/2 salt of 1,5-naphthalindisulfonic acid - colorless prisms from water, pl. 205c, yield 26% of theory. Example 15. (Dimethylamiotilstilmercapto) -ethyl-6-ethoxy-1,2enzisothiazolinone-3. Prepared from bis-N- 2- (2-dimethylminoethyl mercapto} ethylamide 5,5-diethoxydiphenylsulfide-2, 2-dicarboxylic acid.:; Yellowish oil, 35% of theory. EXAMPLE 16 2- (2 -Diethylamino) ethyl-6-butoxy-1, 2-benzisothiazolion-3. Prepared from bis-N- (2-diethylamino) -ethyl-amide 5,5-dibutoxy-diphenylsulfide-2, 2-dicarboxylic acid. A lot of syrup, mole 322 m / e Ci-jH Nj 02 $) (determined by mass spectroscopically). Yield 71.5% of theory.
    Example 17. 2- (3-Dimethyl-amino) -propyl-b-benzyl-1-l, 2-benzisoiazolinone-3 ..
    Prepared from .bis-N- (3-dimethylamino. Propylamide 5,5-dibenzyloxydiphenyl sulfide-2, 2-dicarboxylic acid. Colorless petals from ethyl acetate, mp., Yield 15.5% of theory.
    Example 18. 2- (1-Methylpiperiyl-4) -methyl-b-phenoxy-1,2-benzisothiazolinone-3. ,
    Prepared from bis-N- {1-methylpiperiyl-4) -methylamide 5,5-bisphenoxydiphenyl disulfide-2, 2-dicarboxylic acid. Salt 1/2 1,5-naphthalindisulfonic - crystals, so pl. 173 ° С, output- 15% of the theory.,
    Example 19. 2- {3-Dimethylamino) -propyl-b-phenoxy-1,2-benzisothiazolinone-3.
    Prepared from 5,5-bisphenoxydiphenyl disulfide-2, 2-dicarboxylic acid bis-N- (3-dimethylamino-20 but) propylamide. Yellowish oil. Yield 17% of theory.
    Example 20. 2- (3-Diethylamino-25-but) -propyl-6-phenylmercapto-1,2-benzisothiazolinone-3.
    Prepared from bis-N- (3-diethylamino) -propylamide 5,5-bisphenylmercaptodiphenyl disulfide-2, 2-dicarboxylic acid.
    Salt of oxalic acid - colorless crystals, so pl. 80 ° C, yield 26% of theory.
    Example 21. 2- (1-Methylpiperidyl-4) -g1ethyl-6-phenylmercapto-1,2-benz J isothiazolinone-3.
    Prepared from bis-N- (1-methylpiperidyl-4) -methylamide 5,5-bisphenylmercaptodiphenyl disulfide-2, 2-dicarboxylic acid. Yellowish oil, yield 40 to 18% of theory.
    Example 22. 2- (1-Methylpiperizyl-4) -propyl-6- (4-chlorophenyl) -mercapto-1, 2-benzisothiazolinone-3.
    Prepared from 5,5-bis- {4-chlorophenyl) mercaptodiphenyl disulfide-2,2-dicarboxylic acid bis-N- (1-methylpiperi-45-dil-4) propylamide.
    Disol of oxalic acid - colorless crystals, so pl. 206-207c, 50% yield of theory.
    . Example 23. 2- (2-diethylamino) -ethyl-4,6-dimethyl-1,2-benzisothiazolinone-3.
    Prepared from bis-M- (2-diethylamine-., But) ethylamide 3,5,3,5-tetramethyldiphenyl disulfide-2, 2-dicarboxylic acid. Salt of hydrochloric acid - colorless knobby crystals from methanol, so pl. 241®C, yield 36% of theory .60
    Example 24. (2-Diethylaminoethyloxy) D-ethyl-4,6-dimethyl-1,2benzisothiazolinone-3.
    Semi-ayut from bis-N-C2- (2-diethylaminoethyloxy) ethylamide 3,5,3,5- 65
    -tetramethyldiphenyl disulfide-2,2-di- / carboxylic acid. Salt of oxalic acid - colorless crystals, so pl. 101-102 ° C, yield 45% of theory.
    Example 25, 2- (3-Diethylamino) -propyl-4,6-dimethyl-1,2-benzisothiazolinone.
    Prepared from bis-K- (3-diethylamino) propyl-amide 3,5,3,5-tetramethyldiphenyl disulfide-2, 2-dicarboxylic acid. Yellowish oil. H-NMR (60 MHz, C C, TMS): CE-}, 9.05 (t, 6H), -CHg- 8.20 (KB, 2H), N-CHg 7.50 (m, 6H-) , reTepo-N-CHft- 6.20 (t, 2H), 4-CHi, - phenyl 7.30 (s, 3N), 6-CH-phenyl 7.70 (s, 3N), protons of the aromatic core 5H 3 , 15 (s), 7H 2.90 (s). 23.5% yield of theory
    Example 26. 2- (3-Dimethylamino) -propyl-4,6-dimethyl-1,2-benzisothiazolinone-3.
    Prepared from bis-N- (3-dimethylamino) propylamide 3,5,3,5-tetramethyldiphenyl disulfide-2, 2-dicarboxylic acid. 1/2 salt of 1,5-naphthalene disulfonic acid — colorless, coarse prisms from ethanol, m.p. , yield 40% of theory ,.
    Example 27. 2- (3-Diethylamino) -propyl-5,6-tetramethylene-1,2-benzisothiazolinone-3.
    Prepared from bis-N- (3-diethyl o) propylamide 4,5,4,5-bistetramethylene diphenyl disulfide-2, 2-dicarboxylic acid.
    Yellowish oil. Mol weight. 318 m / / e (C, gH2jNj.OS) (determined by mass spectros | opically). Yield 10% of theory.
    Example 28. 2- (2-Diethylamino) -ethyl-5,6-tetramethylene-1,2-benzisothiazolinone-3.
    Prepared from bis-N- (2-diethylamino) ethylamide 4,5,4,5-bistetramethylene diphenyl disulfide-2, 2-dicarboxylic acid. Yellowish oil. Yield 61% of the theory. H-NMR (60 MHz, CDCfj-TMS): CH 8.95 (t, 6H), -CHjf-CHp- 8.20 (q 4H), aromatic. -CHg 7.20 (m, 4H), N-CHj-CH-g 7.45 (t, 4H), M-CHo-CHj7, 15 (t, 2H), hetero-N-CHj- 6.08 ( t, 2H), protons of the aromatic nucleus 4-H 2.28 (s), 7-H 2.80 (s).
    PRI me R 29. 2- (1-Methylpiperidyl-4) -methyl-5,6-tetramethylene-1,2-benzisothiazolinone-3.
    Prepared from bis-M- (1-methylpiperidyl-4) -methylamide 4,5,4, 5-bistetramethylenediphenIldisul-id-2, 2-dicarboxylic acid.
    Colorless crystals of petroleum ether, so pl. 109 ° C, yield 17% of theory.
    Example 30. 2- (2-Diethylamino) -ethyl-6-nitro-1,2-benzisothiazolinone-3.
    权利要求:
    Claims (3)
    [1]
    Prepared from bis-N- (2-diethylamino) ethylamide 5,5-dinitrodiphenyl disulfide-2, 2-dicarboxylic acid. Light yellow shiny petals of ethanol, m.p. 132c, yield 60.5 theory, Example 31. 2- (3-Diethylamino) -propyl-6-nitro-1,2-benzisothiazolinone-3. Prepared from bis-N- (3-diethylamino-propyl-amide 5,5-dinitrodiphenyl disulfide-2, 2-dicarboxylic acid. Light yellow prisms from ligroin, mp, yield 15% of theory. Example 32. Preparation of 2- (3-diethylamine or propyl ) .- 6-chloro-1,2-benz isothiazolinone-Z. Bis-N- (3-diethylamino) -propylamide 5,5-dichlorodiphenyl disulfide-2,2-di-carboxylic acid is prepared as in Example 16. 31 g of crude product solution 8 ml of gbrom in 30 ml of tetrachloroglero Da, are added dropwise in a mixture of 100 ml of chloroform and stirred additionally for 2 hours, then evaporated in vacuo and the residue is left in Boil with ethanol for a short time. Then evaporate again, absorb the residue with water, separate insoluble parts and basify the clear solution with caustic soda, absorb the precipitated base with ether. Dry the ether solution and evaporate to obtain 13 g (48%). The crude base is dissolved 10 m of methanol and naphthalene disulphonate precipitated by adding 13 g of 1,5-naphthalene disulfonic acid dissolved in acetone. After recrystallization from ethanol with the addition of traces of water, 2- (3-diethylaminopropyl) -b-chloro-1,2-benzisothiazo disulfonate is obtained. Linona-3 in the form of colorless plates, so pl. 255 ° C, yield 85% of theory. Example 33. Preparation of 2- (3-di-n-propylaminopropyl) -6-chloro-1,2benzisothiazolinone-3. To a solution of 14.8 g of 5,5-dichloro-2,2-bis-chlorocarbonyldiphenylsulfide in 100 ml of toluene is added dropwise a toluene solution of 11.05 g of 3-di-n-propylaminopropylamide. After heating for 1 h to a predetermined temperature, the mixture is evaporated under vacuum and the residue is heated from 100 ml of thionyl chloride for 3-4 h to 70 ° C. It is then evaporated again in vacuo, the residue is taken up in water, the aqueous solution is purified with active charcoal, the sodium carbonate ITOM is alkalified, and the reaction product is extracted with ether. After crystallization of the residue of the ether extract from a mixture of acetone and alcohol (4: 1), 1,5-naphthalenedisulfonate with m.p. 200-202 0. Then it is transferred to the base by treatment with a solution of sodium carbonate, etched by ether, the ether extract is evaporated and oxalate precipitated in acetone, m.p. 4®C (after recrystallized acetone), 35% of theory. The claims of the invention for the preparation of isothiazolinone-3 derivatives of total for-chloro, nitro, Cx-C4-alkyl, C-C-alkoxy, phenoxy, phenylmercapto, unsubstituted or substituted by chlorine, or benzyloxy; hydrogen, SU | -C-alkoxy or together with the substituent R forms a tetramethylene group; hydrogen or C-C-alkyl unbranched or branched C;, -C5-alkylene, which can be interrupted by oxygen or sulfur each -C-Cz-alkyl or together with the nitrogen atom form a piperidine or piperazine ring, substituted by C-C4-alkyl with R provided that C;, is C4-alkyl or C-C4-alkoxy; R is hydrogen or C -C-alkoxy; R is hydrogen and A is unbranched C-Sualkylene, then R. And R together with a nitrogen atom cannot ring a piperidic ring, substituted with C-C4-alkyl, due to the fact that phenyl disulfide-2,2-dicarislota of the general formula tO HAH / n I h. R and A have the indicated values, t oxidative cyclization. Collected according to claim 1, characterized in that the oxidation is carried out by treatment with bromine or thionylchloride with respect to claim. 1 and 2, of which the process is in an inert organic solvent environment at 10-100 C. Sources of information are taken into account in the examination of 11 1. US Patent No. 3012029, cl. 260304, published. 1961.
    [2]
    2. The patent of the USA 3617022, cl, 260304, published. 1970. 4. U.S. Patent 3,862,955, cl. 26082066112.
    [3]
    3. US patent No. 3522265, cl. 260304, published. 1970. 304, published. 1975.
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    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    AT219596B|1960-03-24|1962-02-12|Wander Ag Dr A|Process for the preparation of new benzisothiazolone derivatives|
    DE1147947B|1961-07-25|1963-05-02|Knoll Ag|Process for the preparation of new 1,2-benzisothiazolones|
    NZ182325A|1975-11-18|1979-03-16|Beecham Group Ltd|2-substituted-1,2-benzisothiazol-3-ones|EP0000254B1|1977-06-20|1981-06-10|Beecham Group Plc|Antithrombotic 2-propyl)1,2-benzisothiazol 3-one, its pharmaceutically acceptable acid addition salts, their preparation and their compositions|
    DE3226284A1|1982-07-14|1984-01-19|A. Nattermann & Cie GmbH, 5000 Köln|NEW BENZISOSELENAZOLONES, METHOD FOR THE PRODUCTION THEREOF AND PHARMACEUTICAL PREPARATIONS CONTAINING THEM|
    DE3238006A1|1982-10-13|1984-04-19|Bayer Ag, 5090 Leverkusen|AZOLYL METHYLAMINE, THEIR PRODUCTION AND USE IN MICROBICIDES|
    DE3500577A1|1985-01-10|1986-07-10|Basf Ag, 6700 Ludwigshafen|METHOD FOR PRODUCING 1,2-BENZISOTHIAZOLONES|
    US5128457A|1988-07-01|1992-07-07|Miles Inc.|Chromogenic thiol indicators based on an isobenzothiazolone ring system|
    CA1340759C|1988-07-01|1999-09-21|Miles Inc.|Isobenzothiazolone chromogenic thiol indicators and their derivatives|
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    JPH04125580U|1991-05-09|1992-11-16|
    US5734081A|1994-08-05|1998-03-31|Warner-Lambert Company|Arylthio compounds|
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    US5620997A|1995-05-31|1997-04-15|Warner-Lambert Company|Isothiazolones|
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    US10058542B1|2014-09-12|2018-08-28|Thioredoxin Systems Ab|Composition comprising selenazol or thiazolone derivatives and silver and method of treatment therewith|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    DE2602643A|DE2602643C2|1976-01-24|1976-01-24|1,2-Benzisothiazolinone-3, process for their preparation, as well as pharmaceuticals|
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