• 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:
    Peperidine derivs. of formula (I) are new: (R1 = H, branched, linear or cyclic, opt. unsatd., aliphatic hydrocarbyl, aryl or heterocyclyl, all opt. substd.; R2 = H, OH, OR', SH, SR', NH2, NHR', NR'R", NH2CH2, R'NHCH2, R'R"NCH2, COOH, COOR', HOCH2, R'CONHCH2, R'CONR"CH2, R'SO2NHCH2, R'SO2NR"CH2, R'NHCONHCH2, R'NHCSNHCH2, R'OCONHCH2, SO3H, CN, CONH2, CONHR' or CONR'R"; R3 can be as R1 but is pref H, CH3, CH2OH, CH2NH2, CH2NHR', CH2NR'R", R'CONH.CH2, R'CONR"CH2, HalCH2, R'OCH2, R'COOCH2, R'SO2OCH2, R'SO2NHCH2, R'NH.CONHCH2, R'NHCSNH.CH2, R'OCONHCH2, CN, COOH, COOR', CONH2, CONHR', R'SO2NR"CH2, CONR'R"; R' and R" are as for R1; when (i) R3 = CH2OH; R2 = H or OH; (ii) R3 = CH2NH2 and R2 = OH; and also (iii) when R3=H, R2=H, OH, SO3H, CN or CH2NH2, R1 cannot be H). (I) inhibit alpha-glucosidases, esp. disaccharidases, so are useful in treating pre-diabetes, gastritis, obstipation, caries, gastro-intestinal infections, meterorism, flatulence, hypertension, atherosclerosis and esp. adiposity, diabetes and hyperlipoproteinaemia. They are also useful as animal feed additives to improve the meat-fat distribution.
    公开号:SU917697A3
    申请号:SU782652748
    申请日:1978-08-25
    公开日:1982-03-30
    发明作者:Юнге Бодо；Петер Краузе Ханс；Мюллер Лутц；Пульс Вальтер
    申请人:Байер Аг (Фирма)；
    IPC主号:
    专利说明:

    The invention relates to a method for producing new 3,4,5-trioxypyridine derivatives, which can be used in medicine as a remedy for diabetes, hyperlipemia and obesity, as well as an agent that influences the ratio of meat and fat in favor of meat. animals. Derivatives of 3,4,5-trioxypyridine, in particular, 1-deoxinoiairimycin, are known, which can be used as a remedy for diabetes, hyperlipemia and obesity, and also as an agent that influences the ratio of meat and fat in favor of meat. animals ij The known method of alkylation of amines with apkyl halides or aldehydes in the presence of a reduction of $ 1E. The goal is achieved by the fact that in the method of obtaining the derivatives of 3.4 5-trioxypyridine of the general formula YO CH20H. BUT where R is alkyl with the number of carbon atoms from 1 to 18, unsubstituted or substituted by hydroxyl, alkenyl with the number of carbon atoms from 2 to 12, alkynyl with three carbon atoms, cyclopentyl, cyclohexyl, deoxyglucythyl or Cv-Cj- alkyl, substituted pyricyloch, glucopyranosylmercapto, epoxy ,. N-phthalimido, amino, carboxyl, or cyclohexyl, cyclohexenyl, norbornenyl, benzylaminocarbonyl, C, -C4-alkyl-; aminocarbonyl, cyclohexylaminocarbonyl, phenylaminocarbonyl, methoxy, methoxyethoxy or alkylthio groups with 1 to 2 carbon atoms in the alkyl chain, cyano group, or phenyl, unsubstituted or substituted, methyl, chlorine, nitro, carboxylic, phenyl, or phenylphenyl or phenylphenyl, or phenylphenoxy; compound of formula. .. The BUT is alkylated with an appropriate halogen-derivative in the presence of an acid binding agent or with the appropriate aldehyde E. in the presence of a resorbent followed by release of the desired product as a base or cone. The process is preferably carried out in the presence of a solvent. Example 1. S - Methyl-1-deoxyinurimirization (Z,) To 4 MP of 98% formic acid, cooled with ice, add 3.2 g of 1-deoxioxyuriymicin and 2 MP of 30% aqueous formaldehyde. Then it is heated for 8 hours with a reverse cooler. After cooling, the reaction mixture was diluted with acetic acid. Vypa gives resinous sediment. The acetone solution is decanted and the resin is washed several times with acetone. The residue is dissolved in distilled water and the solution is freed from formic acid by the addition of the basic ion exchanger in the form of ®OH (AtberEite JRA 410). The exchanger is filtered off and the aqueous solution is dried under reduced pressure, - 3.9 g of smear N-methyl-1-deoxinoinomyrimia are melted. The compound can be further purified by chromatography on cellulose. Water-containing butanol is used as an auxiliary agent. M.p. 153 C (ethanol). Mass spectrum: the main peak in the upper mass region is at m / e 146 (M-CH1OH). DP of further characterization of the compound in acetone anhydride / pyridine (1: 1), at room temperature, translates the compound N-methyl-2, 3,4,6-tetra-o-acetyl-l-desoxynyyrymyrimidine into peracetylating. From this derivative, at 100 MHz, the proton resonance spectrum is measured: between 2.0 and 2.1 hours per mpn. finds 4 singlets in general for 12 protons, which correspond to the methyl groups of the o-acetyl groups (SC –O – C – U. St. V–,. i c O and the nN methyl group (CHj – K are found as a singlet at , 45 hours per mpn. Between b 2.1 and 2.5 ppm, they absorb, as a bad effect, broken multiplets, two protons, 4 the C-atom bound to nitrogen (HyC-N A further similar proton It is taken as a doublet of doublet (J 11 Hz,} Hz) at 6 z3, l8 parts per mnp. At ff: 4.16 and 4.22 parts per mn. Absorbs methyl group f-Qlj-OC-CH as the AV system. The remaining three proto from (yr-C-SNSL is considered as a multinTT between 9.4.9 and 5 , 2 hours on mpn .... Example 2. Nn-butyl-1-, -deoxyneiomyricmicin (I, R -CH, -CHHCHNCHN). To 3.2 g of 1-deoxinoimiomycin (0.02 mol) 12.0 ppm of n-butyraldehyde, 0.01 mol of methanolic HCt and 1.5 g of NaCNBHj are successively supplied in 40 MP of absolute methanol, cooled with ice and stirring. The reaction mixture is stirred for 12 hours at room temperature. Then it is evaporated to dryness rotary evaporator. The residue is dissolved in 50 mp of water and 3 paqa are extracted, each time with 30 MP CHCtj. The aqueous phase is dried, the residue is taken up in 30 ml and fed to a coil with a length of 50 cm and a width of 2 cm, which is filled with a strongly basic ion exchanger in a fork IT (Amberfite JRA 400 or Dpwex) Throw out water and separate fractions are examined by thin layer chromatography (silica gel plates, the solvent is the ester of acetic acid: methanol: water: 25% ammonia 100: 60: 40: 2; spray reagent solution KfbiOi,). The fractions which contain Nn-butyl-1-deoxyenoimyrimycin are combined and the aqueous solution is concentrated on a rotary evaporator. The residue is grilled, and crystallization begins. The crystals are sucked off, washed with water and dried. Obtain 3 g of Nn-butyl-1-desoxinomyrimicin with so pl. 126127C. Mass spectrum: the main peaks in the upper mass region are found at m / e 188 (M-CH2OH) and m / e 176 (,; With less reactive aldehyde 1X), the following molecular mixture is fed into the reaction mixture. The following compounds are obtained in the same way. N-Ethyl-1-desoxinoyirimycin (I, R-CHiCT), Mass spectrum: an intense peak at m / e 160 (). NH-Propyl-1-deoksnnoyrimycin (I, R-CH СНцСНъ). Mass spectrum: intensive peak at m / e, 174 (M-SNGON). In addition, the peak at m / e 206 (M + H) and m / e "204 (M-H). N-Isobutyl-1-deoxineyomyrimycin. CH / ( I, R -). Mass spectrum: the main peaks in the upper mass region are at / e 5 188 (), SNS t / e "176H-CHT / e 220 (M + H). SKZ. Nn-Heptyl-1-deoxinoinomyrimycin (I, R" -CH .-- (CHt) $ - CH). TPL 111113 C (acetone); mass spectrum: the main peak in the upper mass region at m / e 230 (M-CHtOH), in addition, the peak at ha / e 262 (M + H) and t / e 260 MN) N-Benzyl-1-desoxinomyrimycin
    ; i,
    Mass spectrum: the main peak in the upper mass region at
    m / e 222. (M-CHiOH); m.p. 183-184C (methanol).
    N7 (2-Pyridyl) -methyl-1-deoxin i
    Yrymtsin (I, R - CHj
    i.Masspectral: the main peaks in the upper mass region are found at w / e 255 (M + H), m / e 236 (M-HjO) and m / e 223 (M-NaOHON); m.p. 174-175C (ethanol).
    N-2-Hydroxyethyl-1-desoxinomyrimycin (I., R - CHNCHOH). Mass spectrum: the main peak in the upper mass region lies at m / e 176 (M-CHj OH); m.p. 147-149 C (ethanol).
    N-2,3-Dioxy-n-propyl-1-desoxinoimyrimycin (1, I-CH2-CH-CH.20H).
    HE
    rtacc spectrum: the main peaks in the upper mass region lie at m / e 206 (M-SNGON) and m / e 17.6; m.p. 155-156C (after fractional chromatography).
    Nr (S-D-Glucopyranosyl-2-mercaptoethyl) -l-desoxycinoymyrimicin (I, R
    HE
    OH he), Mass Spectrum
    CH,
    ck
    SNGON (measured in the compound percetolized in pyridine / acetanide RID): the main peaks in the upper mass region are found at m / e 648. (K-CH g-COS-CH 3), m / e: 588 and m / e 344 Needed for interaction the aldehyde is obtained from o-acetylated 1-thioglucose and chloroacetaldehyde. The acetyl group is cleaved in the final product by transesterification with a catalytic amount of NaOCHj in methanol. M-Oxiranyl-methyl-1-deoxinoimirimycin (1, R — CHj — CH — CHg). Mass spectrum: the main peaks in the upper mass region are found at m / e 219 (M t / e 202, m / e 188 (M-CHj, OH) and w / e - 176 (m-CE-CH,) t.pl , 135-137 C NO / post-fraction chromatography). NY- (3-Y-phthalimil-n-propyl) -1-deox
    Noiruimicin; (|, R-CHi-CHfCHi-N
    Mass spectrum: the main peaks in the upper mass region are found at t / e "348, t / e 319 (), t / e - 301, t / e 200, t / e" 188, t / e - 174 , m / e - 160, to m / e 147. Cleaning the connection wire -; by evaporation with acetone and recrystallization from ethanol, m.p. 208210С.
    N- (3-Amino-n-propyl) -1-desoxinoimyrimycin (I, R-C1-CHt-CHtNHi). Mass spectrum: the main peaks in the upper mass region lie at m / e 189 (M-SNGON) and w / e 146.
    N- (1-Deoxinoiomyrimicin-yl) -acetic acid (I, R-CH 2 COOH). Mass spectrum: the main peaks in the upper mass region are found at w / e 203 Jl-HiO), n1 / e 159, m / e 145 to m / e 100. Purification of the compound is carried out by recrystallization from methanol / water, m.p. 187-188p.
    N-o-Hnitrobenzyl-l-desoxycinoymyrimicin (l, R-CHj
    Rf value
    thirty
    0.85 (on silica gel tiles Silica gel 60, produced by Merck, Germany, solvent. Acetic acid ester: methanol: Ng. O: 25% ammonia 100: 60: 40: 2)
    N-o-Carboxybenzyl-1-desoxinomyrimicin JDst - OHJ.
    Rf is 0.7 (tiles and solvent as above). Hn-Carboxybenzyl-1-deoxine P- “-“ - °° b a value of 0.7 (tiles and solvent as described above). M.p. 280-281 C (methanol). M-Cyclopentyl-1-desoxinoimyrimycin (-). T.pl. 89-90C. N-e-Cyanethyl-1-desoxinomyrimycin (I, R-CHj-CH -CN). M.p. 135 С N- (4-Phenoxybenzyl) -1-deoxinoit. Pl. 109-112-C. , N- (Buten-2-yl) -1-desoxinoimyrimycin (I, R-CH, -CH CH-CHj). M.p. 120-123 C. M-undecen-10-yl-, 1-desoxinomyrimycin (l, R / - (CHi) j-CH CH). M.p. 144-146 C. N- (5,5,7, 7-Tetrametiloctene -2-yl -1-desoxinoiomyrimicin I, R - CH on, CH, CH-CH, -C-CH, -C-CH3) .112 -118 II CH3 CH3; Example 3 .M-s-phenylethyl-1-ez synyrimymicin (l, c - cn, -sn to 2 g of 1-lezozinoiomyrimicin and I, in acetic acid in 40 ml of methanol are added 3 g of phenylacetaldehyde and 0.8 g of NaCNBHj is then stirred overnight at room temperature.The reaction mixture is dried on a rotary evaporator.The residue is dissolved in ethanol / Hg / O (2: 1) and applied to a column filled with strongly SOUTHY ion exchangers in the form H® (Ambertite 3R 120). The column was washed with 2 L of ethanol / H 2 O. (2: 1 Then the reaction product is washed from the column using ethanol / 2% aqueous NHjj (2: 1). Separate fractions are examined by thin-layer chromatography and those fractions that hold NA-phenyleth. L-1-deoxyenoimyricin The residue is crystallized from approximately 100 ml of ethanol. The resulting H-α-phenylethyl-1-deoxynomyrimycin is combined and dried. The residue is crystallized from approximately 100 ml of ethanol. The yield is 2.5 g of M-α-phenylethyl-1-deeoxinoimyrimycin, m.p. 179-131 ° C. The following compounds are prepared in a similar manner. Nn-Pentyl-1-desoxinoyrimycin (I, R - (CHi) c-CH5). T. pl. 97 ° C (from acetone), Nn-Hexyl-1-desoxinoimyrimycin (I.R (CHi) ff-CH5). T. pl. 112-113s (from ethanol / acetone mixture). Mn-Octyl-1-desoxinoyrimycin "(t, R - (SNg) 7-CH,). M.p. 115-117 ° C (from ethanol / acetone mixture). Nn-Nonyl-1-desoxinoyrimycin (I.R - (CHg.) A-CH.,) So pl. lOS-iOl (from ethanol / acetone mixture) Ln-Decyl-1-deoxinoinomyrimicin (I.R - (CH g) e-CH). Mp.151 ° C (stored at 91 ° C from methanol / ac tone). Nn-undecyl-1-deoxinomyrimicin (I.R - (CHi) -CH ,,). T. pl. 162C (sintered at 97 ° C, from ethanol / acetone mixture) Mn-Dodecyl-1-deoxinoimirimycin (I. (CHi) -CH) .Т. square 164 ° C (speci fi ed from ethanol / acetone mixture). -. . Nn-Tetradecyl-1-desoxinomyrimycin (1, R - (CHL) 4-CHb). So pl. 105107 C (from methanol). N-H- (5-Oxypentyl), - 1-deoxy-irimycin (1, R - (cHi) 4-CHiOH). M.p. 86-87 with (from butanol). M-Cyclohexylmethyl-1-desoxinomyrimicin (l, R "-CHj- / j Tpl. 138140 ° C (from acetone). M-Cyclohexyl-1-deoxinoinimyrimina Chin 1, Kg Y Rf value 0,58, ethyl acetate / ethyl acetate / water / 25% ammonia water (120: 70: 10: 1), 60 F 254 silica gel tiles from Merck foreign company, Germany. N- (3-Cyclohexenylmethyl) -1-deoxyinomyrimicin {g, R - СЮ2- (УТ .PL. 142-144 0 (from acetone).,. N- (2 -Norbornen-5-yl-methyl) - 1; ω-isoxinineyrimycin (I, c - Sn, Y 7 mp. 1-O-162 "C (from ethanol Mn-Hl6rbenzyl-1-desoxinoimyrii II, R -GHj, - / Qyci) T. pl. 153ISS C (from acetone). N-Isopropyl-1-desoxynyyrimitsin (I, (CHj) i) .Rf value 0.45, ethyl acetate / methanol / water / 25% ammonia water (120: 70: 10: 1), silica gel tiles of brand 60 F 254 from Merck foreign company, Germany. Nm-Methylbenzyl-1-deoxynyrimyricin (l, R - T.pl. 134136 s (from methanol). N- (p-Biphenylmethyl) -1-deoxinoinomyrimitsi (I, K -) m.p. (I, R - CH- {CH je-CH3) mp 125-127 ° C (from ethiol). N - (1-Methyldecyl) -1-deoxinomyrimycin (I, (Chfe) s -CHj). The value of Rf 0.79, acetic ester / methanol / water / 25 per ammonia water (120: 70: 10: 1), 60 F 254 silica gel tiles from the Merck foreign company, Germany. Example 4-. M-Allyl-1-desoxinomyrimycin (I,). 5 g of 1-deoxinoirimycin in 30 ml of dimethylformamide and 30 ml stirred with 5 g and 5 g of allyl bromide for 3 hours at room temperature. Then the silver salts are filtered. stand out and the filtrate is dried in a rotary evaporator. The residue is recrystallized from ethanol. Yield: 4.5 g of H-allyl-1-deoxychoichyrimicic with so pl. 131-132C. The following compounds are prepared in a similar manner, and the isolation and purification of the final product is also carried out by chromatography over strongly acidic ions (H®-form). N-propargyl-1-desoxinomyrimycin (I, .- CHCH). T. pl. leoc (from acetone. N- (3,4-Dichlorobenzyl) -1-deoxy-Cl T. mp noirimycin l 130-132 ° C. N- (p-Nitrobenzyl) -1-deoxinoimir mycin (1 ,, H | O / - Og) mp. 14 .. N- (m-Nitrobenzyl) -1 -sezoksinoinyrimytsitsin, R - CH2 - and) U) T. square 168 170 ° G. N- (1-desoxinomyrimyl-yl) -acetic acid benzylamide (1, R-CHj-CO, mp. 129 C. Mass-to-spectrum: the main peaks in the upper mass region are at, m / e 292 , m / e 279, m / e 203 and m / e 106. N- (1-desoxinoyrimicin-yl) acetic acid n-butylamide (I, -CO-NH- (CHi) S-CH)). Mass spectrum : The main peaks in the upper mass region are at m / e 245, m / e 203, m / e 176, m / e - 159 and m / e 145. N- (| -Methoxyethyl) -1-deoxyinomyrimycin (i, .CHi -OCHj. Rf value of 0.57 (thin-layer chromatography on silica gel tiles, silica gel 60 from Merck, Germany, the solvent is ethyl acetate / methanol / HiO / 25% ammonia 100: 60: 40: 2). N- (-Methyl ercaptoethyl) -1-cesoxinoyrimycin (1, CHj -S-CHj). Mass spectrum: the main peaks in the upper mass region lie at m / e 220, p / e 206 and m / e 176. N - (- Ethylmercaptoethyl) - 1-Cezoxinoiomycin (I, .- CHi.-S-CHi-CH Mass spectrum: the main peaks in the upper mass region lie at w / e 220 and m / e 176 .... (-Methoxy) -ethoxyethyl 1 -1- desoxinoyrimycin (I, K-CHNg-CHg-0-CHg-CHj.-OC (). Mass. Spectrum: the main peaks in the upper mass region lie at m / e 234 and m / e 176. Further peaks are found at m / e 218, m / e 204, m / e 158, m / e 146 and m / e 132. N- (l-Dezo-oxiglucythyl) -l-desoxy-OH H OH H OH OH OH irimycin (I, B -j-I111 -) - H) H OHH HH Mass spectrum: ra / e 296 (20%) , 278 (15%); 176 (100%), 158 (30%), 132 (30%). N-Zinnamyl-l-deo-xoxino and ipsi shtsin. (1, K-CHN.-CH CH-SbN5). M.p. 163-0, N- (2-Cyclohexylaminocarbonyl-. Ethyl) -1-deoxinoimiomycin (1, R-CH.j; -CH2-CO-1TN- / H). Mp. . M- (2-Phenylaminocarbonylethyl) -. cesoxinoyrimycin (I, R-CHiCH-COT. mp. 145 ° C. Example 6. H-Hexadien-2,4-yl-1-deoxinoimyrimycin (I, R-CHt- (CH CH) 2.-CHj). A solution of 5 g of 1-deoxyniomyrimycin in 100 ml of methanol and 4.5 ml of glacial acetic acid is mixed at 4 ° C with 4.4 ml of hexadienal and 3 g of sodium cyanoborohydride. After stirring for 1 h at 0 ° C, it is stirred for 19 at room temperature. They are dried to dryness, the residue is taken up in water and applied onto a column 120 cm long and 3.5 cm in diameter, containing pulp as the stationary phase and acetone as the mobile phase. Cozy with acetone and then with acetone, to which up to 30% water is gradually supplied. Separate fractions are checked by thin layer chromatography, the fractions containing the above product are combined and concentrated. After crystallization with acetone, 4 g of the above compound with an Rf value of 0.55 (solvent - chloroform / methanol / aqueous ammonia (4: 3: 1), Rf value for 1-deoxynomyrimycin 0.21, mp 172-173 ° C. Similarly, the following compounds L-Heptadiene-2,4-yl-l-deoxyxinoyrimycin (I, R-CHt- (CH CH) j. -CH j.-CHb) are prepared. Rf value is 0.57, Rf value for 1 - duoxoinomyrimicin 0.21. M.p. 135-137 ° C. Example 7: M-Hexadiene-2,4-yl-1-deoxinomyrimycin (I, R-CHi- (CH. SN) -CH) A solution of 25 g of 1-deoxineyomyrimycin in 500 ml of methanol and 22.5 ml of glacial acetic acid are mixed at 0 ° C with 22 ml of hexadienal and 15 g of sodium cyanoborohydride. After stirring for 1 h at 0 ° C
    权利要求:
    Claims (2)
    [1]
    Claim
    1. The method of obtaining derivatives
    3,4,5-trioxypyridine of the general formula 1 wherein R is C <-C <4 -alkyl unsubstituted or substituted with hydroxyl, C g-C (1. -Alkenyl C-alkynyl, cyclopentyl, cyclohexyl, deoxyglucytyl or C <. -C 5 alkyl substituted pyridyl, glyukopiranozilmerkapto-, epoksi7 N-phthalimido, amino, carboxy or cyclohexyl, cyclohexenyl, norbornenilom, benzilaminokarbonilom, C <-C alkylaminocarbonyl V, tsiklogeksilaminokarbonilom, fenilaminokarbonilom, methoxy, methoxyethoxy or alkylthio with 1-2 carbon atoms in the alkyl chain, cyano group, or phenyl, not or ameschennym. substituted by methyl, chlorine, nitro, carboxyl or phenoxy, or wherein the compound of formula. II
    CH 2 0H of their phenyl salts, in that they are subjected to alkylation with an appropriate halogen-derivative in the presence of an acid-binding agent or with an appropriate aldehyde in the presence of a reducing agent, followed by isolation of the target product in the form of a base or salt.
    [2]
    2. The method according to claim 1, they are distinguished by the fact that the process is carried out in a solvent environment.
    类似技术:
    公开号 | 公开日 | 专利标题
    FI81087C|1990-09-10|Process for the Preparation of New Therapeutically Useful 1-Acyl-2-a zabicyclo [3.3.3] -3-Carboxylic Acids
    US6063806A|2000-05-16|Indolyl or indolinyl derivatives and medicinal use thereof as ACAT or lipid peroxidation inhibitors
    SU1614759A3|1990-12-15|Method of producing amides, their diastereomers, racemates or their acid-additive salts
    SU1320207A1|1987-06-30|Dextrorotatory enanthiomer or |-alpha-ethyl-2-oxo-1-pyrrolidineacetamide possessing mnesic activity
    SU727142A3|1980-04-05|Method of preparing substituted 1-sulfonidebenzimidazoles
    IE914518A1|1992-07-01|N-acyl-2,3-benzodiazepine derivatives, pharmaceutical¹compositions containing them and process for preparing same
    SU1042617A3|1983-09-15|Process for preparing derivatives of northropanole or their salts
    EP0242167B1|1991-11-27|Heterocyclic carboxamides
    SU504480A3|1976-02-25|Method for producing amides of | -piperidyl-4 -) - | -carboxylic acid or their salts
    US5232948A|1993-08-03|Substituted monocyclic aryl compounds exhibiting selective leukotriene b4 antagonist activity
    SU917697A3|1982-03-30|Process for producing derivatives of 3,4,5-tri-hydroxypyridine or their salts
    PL126032B1|1983-07-30|Process for preparing novel derivatives of 5-phenyl-2-hydroxytetrahydrofuran
    SU1156593A3|1985-05-15|Method of obtaining benzamide derivatives or their acid-additive salts or optical isomers
    US5554622A|1996-09-10|Asymmetrically substituted bisnaphthalimides
    HU195486B|1988-05-30|Process for preparing new pyridine derivatives
    CS231214B1|1984-10-15|Processing method of 1-substituted n+l8alpha-ergoline+p-n,diethyl urea
    Wang1974|Synthesis and properties of N-acetimidoyl derivatives of glycine and sarcosine
    SU847923A3|1981-07-15|Method of preparing 7-beta- d-2-amino-2-|-acetylamino-3-methoxy-3-cephem-4-carboxylic acids or their salts
    US4353911A|1982-10-12|Indolo|quinolizidines, useful in increasing femoral and vertebral blood flow
    Moormann et al.1990|Potential antisecretory antidiarrheals. 2.. alpha. 2-Adrenergic 2-[| alkyl] imidazolines
    FI74960B|1987-12-31|FRUIT PROCESSING OF PHARMACOLOGICAL PROPERTIES OF 1-FURYL-3,4-DIHYDROISOKINOLINER.
    SU1015828A3|1983-04-30|Process for preparing derivatives of pyrazolo | quinazoline or their salts
    US4503236A|1985-03-05|Antiallergic 4Hfuro[3,2-b]indoles
    JPH08269008A|1996-10-15|Compound having distamycin-like structure and antitumor agent containing the compound
    SU803859A3|1981-02-07|Method of preparing omega-thiopropionamides or their acid-additive salts
    同族专利:
    公开号 | 公开日
    DE2738717A1|1979-03-08|
    ZA784842B|1979-08-29|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    RU2678085C2|2014-07-21|2019-01-23|ДИФАРМА ФРАНЦИС С.р.л.|Iminosugar in crystal form|
    RU2743694C1|2019-12-04|2021-02-24|Общество с ограниченной ответственностью "29 февраля"|Miglustat n-butyl-1,5-dideoxy-1,5-imino-d-glucitol|
    RU2762605C1|2020-12-28|2021-12-21|Нестерук Владимир Викторович|Method for producing -1-butyl-2-piperidine-3,4,5-triol|
    DE2830469A1|1978-07-11|1980-01-24|Bayer Ag|PRODUCTION OF L-DESOXY-NOJIRIMYCIN AND N-SUBSTITUTED DERIVATIVES|
    DE3049446A1|1980-12-30|1982-07-29|Bayer Ag, 5090 Leverkusen|METHOD FOR PRODUCING 1,5-DIDESOXY-1,5-IMINO-D-GLUCITOL AND ITS N-DERIVATIVES|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    DE19772738717|DE2738717A1|1977-08-27|1977-08-27|Tri:hydroxy-piperidine derivs. - useful as glucosidase inhibitors for treating diabetes etc. and as animal feed additives|
    [返回顶部]