• 专利附录
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  • 权利要求
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    • 专利摘要:
    Bicyclo[3.1.0] hexyl-substituted carbonylaminophenoxy compounds of the formula …<CHEM>… where R is i-propyl or t-butyl; R<2> is H, halo, CN, C1-2 alkyl, C1-2 alkoxy, acetyl or propionyl; Y is >NR<5> where R<5> is H or methyl; n is 0 or 1 and m is 1 or 2; and their pharmaceutically acceptable salts; and pharmaceutical compositions containing such compounds, can be used for treating cardiac disorders, hypertension and glaucoma in mammals, and may have local anesthetic properties. They can be prepared by reaction of isopropylamine or t-butylamine with the corresponding compound having …<CHEM>… in place of -OCH2CH(OH)CH2NHR, or by hydrolysing the corresponding compound having …<CHEM>… in place of -OCH2CH(OH)CH2NHR, in which R<3> is H, alkyl or optionally substituted carbocyclic aryl.
    公开号:SU854271A3
    申请号:SU792788053
    申请日:1979-07-02
    公开日:1981-08-07
    发明作者:Джордж Унтч Карл；Мехмет Беркоз Белиг；Говард Унгер Стефан
    申请人:Синтекс /Ю.С.А./ Инк (Фирма)；
    IPC主号:
    专利说明:

    where R has the above meanings, O R is a group of the formula -Cd-CH with an amine. There is also known a method for the preparation of ureidophenoxy-2-hydroxy-3-aminopropanes of the general formula V 0-CH2-Jll- (H2-NH, where R and Rj are aliphatic coal prenatal sludge together - bivalent hydrocarbon residue - cycloaliphatic, R /, - lower alkyl , cyclo-kil and others, with the ureido residue in the meta or para position with respect to RO, a residue consisting of a compound of the general formula where R, R j and R are as defined, is reacted with a compound of the general formula Z --CH2-; H-CH2-NH-R5 where is RT, is as defined above, together with Z forms epoxy Group 2, The purpose of the invention is to expand the range of agents emitted on a living organism. The aim is to ensure that the compound of the general formula OCH —CH — CH where R and R-are as defined above, is treated with isopropylamine or tert-butylamine followed by isolation of the desired product in free form or as a salt. Preferred inorganic salt anions include chloride, bromide, iodide, sulfate, phosphate, nitrate, etc. Preferred organic anions are acetate, benzoate, lactate, ropionate, butyrate, valeriate, tartrate, maleal, etc. Example 1. (t) 1-Isopropylamino-3- (endobicyclo Cz. 1. About hex-b-yl) -ethylureido -1-phenoxy -2-propanol. 5 ml of isopropylamine are added to a solution of 10 g of 1,2-epoxy-3- ((endobicyclo 3 .1. OD hex-6-yl-ethylureido -1-phenoxy) propane in 20 ml of methyl alcohol. The mixture is stirred at room temperature within 20 hours. The product is isolated on thin-layer plates to obtain 910 mg of the above desired product, mp 102-104 ° C. Using other epoxy compounds, the propanols listed below are obtained in a manner analogous to that described above using isopropylamine and tert.- butylamine respectively. All compounds are isolated as racemates (±): 1-tert-butylamino-3-4- f2- (endobicyclo Sz. 1. 0 hex-6-yl) -ethylureido -1-phenoxy) -2-propanol, 1-isopropylamino-3-2-acetyl-4- 2- (endobicyclo 3.1.0 hex-b- yl) -ethylureido -1-phenoxy -2-propanol, 1-tert.-butylamino-3-2-acetyl-4- 2- (endobicyclo Z. 1. O gax-b-yl) -ethylureido -1-phenoxy} -2-propanol, 1-isopropylamino-3- 4- (endobicyclo Gz. 1. o1 hex-b-yl) methylureido -1-phenoxy} -2-propanol, mp. 91-93 C 1-tert.-butylamino-3-4- Ozndobicyclo D.1.o hex-b-yl) methylureido -1-phenoxy, -2-propanol, mp. 99lOl C, 1-isopropylamino-3- | 2-chloro-4-G2- (endobicyclo Z. 1. o hex-b-yl) ethyl-M-methylureido -1-phenoxy -2-propanol, m.p. 77-78 ° C, 1-tert.-butylamino-3- 2-chloro-4-t2- (endobicyclo 3.1. 0 hex-6-yl) -ethyl-N-methylureido -1-phenoxy} -2-propanol, 1-isopropylamino-3-C4-C2- (endobicyclo 3.1.0 hex-b-yl) ethyl-N-methylureido -1-phenoxy -2-propanol, mp. 125-12b ° C, 1-tert.-butylamino-3-C4- 2- (endobicyclo 3 .1.0 hex-b-yl) ethyl-M-methylureido -1-phenoxy) -2-propanol, 1-isopropylamino- H- (2-cyano-4- 2- (end of bicycle; about 3.1. Of hex-b-yl) -ethylureido -1-phenoxy) -2-propanol, 1-tert.-butylami.no-3- 2- cyano-4- 2- (endobicyclo z. 1. o hex-b-yl) ethylureido -1-phenoxy -2-propanol, 1-isopropylamino-3- | 2-chloro-4- 2- (endobicyclo 3.1-0 gxs-b-yl) -ethylureido -1-phenoxy -2-propanol, 1-t. Tert-butylamino-3- 2-chloro-4- .2- (endobicyclo D. 1. o hex-b-yl) -ethylureido -1-phenoxy} -2-propanol,
    1-isopropylamino-3- 4- 2- (endobicyclo t3 .1.0 hex-b-yl) ethylcarbonylamino -1-phenoxy) -2-propanol, m.p. llS-llV c,
    1-tert.-butylamino-3- (endobicyclo 3.1. O hex-b-yl) ethylcarbonylamino-1-phenoxy-2-propanol,
    1-isopropylamino-3- (2-acetyl-4- 2- (znobicyclo 3. 1.0 hex-6-yl) -Lylcarbonyllag Shno-1-phenoxy-2-propanol,
    1-tert.-butylamino-3- 2-acetyl-4- 2- (endobicyclic. 1, o-hex-6-yl-ethylcarbonylamino -1-phenoxy-2-propanol,
    1-isopropylamino-3-2-chloro-4- 2- (endobicyclo {3.1.o hex-b-yl) -ethylcarbonylamino3 - -fechoxy) -2-propanol, mp, 131-133 ° С,
    1-tert.-butylamino-3- 2-chloro-4- 2- (endobicyclo s. 1. Oj hex-b-yl) ethylcarbonylamino -1-phenoxyX-2-propanol.
    Example 2. Obtaining salts of compounds of the formula T.
    1 g of 1-isopropylamino-3- | 4- 2- (endobicyclo 3.1.o hex-b-yl) -ethylureido -1-phenoxy -2-propanol is dissolved in 10 ml of sulfuric ether at 20c. A stream of gaseous anhydrous hydrogen chloride is passed over the surface of the solution until the moment when the supernatant becomes colorless. The resulting precipitate is filtered off, washed with ether and then crystallized from a mixture of methyl alcohol - sulfuric ether.
    Crystalline 1-isopropylamino-3 - (((endobicyclo 3.1. O hex-b-yl G-ethylureido-1-phenoxy) -2-propanol is obtained.
    Example 3. B5 MP ethyl acetate and paq at 20 ° C 1 g of 1-isopropylamino-3- (4- 2- (endobicyclo (3.1.0 hex-6-yl) -ethylureido -1-phenoxy) -2-propanol. To the resulting solution was added 10 ml of a saturated solution of maleic acid in sulfuric ether. The mixture was kept at room temperature for 1 hour. The resulting precipitate was filtered off.
    trigen shed with sulfuric ether and then crystallized from a mixture of sulfuric ether - ethyl alcohol (10: 1). Crystalline 1-isopropylamino-3- ((endobicyclo C3.1.0 hex-b-yl) -ethylureido-1-phenoxy) -2-propanol maleate is obtained.
    .
    权利要求:
    Claims (2)
    [1]
    1. cdCP patent 423291, class C 07 C 93/06, published. 1974, issued to a foreign firm KHBeringer Zon, Germany.
    [2]
    2. Patent of the USSR 450397, cl. C 07 C 93/06, publ. 1974, issued to a foreign company TsibaGeigi, Switzerland.
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    法律状态:
    优先权:
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