DD224596A5 - Procede de preparation de benzyl-phenyl-osides utiles en therapeutique - Google Patents

Procede de preparation de benzyl-phenyl-osides utiles en therapeutique Download PDF

Info

Publication number: DD224596A5
Authority: DD; German Democratic Republic
Prior art keywords: group; para; phenyl; xyl; preparation
Prior art date: 1983-07-20

Application number

DD84265446A

Other languages

German (de)

English (en)

Inventor

Soth Samreth

Francois Bellamy

Jean-Bernard Chazan

Original Assignee

Sori Soc Rech Ind

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1983-07-20

Filing date

1984-07-19

Publication date

1985-07-10

1984-07-19 Application filed by Sori Soc Rech Ind filed Critical Sori Soc Rech Ind

1985-07-10 Publication of DD224596A5 publication Critical patent/DD224596A5/de

Links

238000002360 preparation method Methods 0.000 title description 29
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
125000005843 halogen group Chemical group 0.000 claims abstract description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims abstract description 5
229910052799 carbon Inorganic materials 0.000 claims abstract description 5
150000003839 salts Chemical class 0.000 claims abstract description 4
125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims abstract description 3
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims abstract description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims abstract 2
150000001875 compounds Chemical class 0.000 claims description 18
238000000034 method Methods 0.000 claims description 15
239000000203 mixture Substances 0.000 claims description 15
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 12
238000003756 stirring Methods 0.000 claims description 10
239000003638 chemical reducing agent Substances 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 6
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 6
150000001412 amines Chemical class 0.000 claims description 5
229910052794 bromium Inorganic materials 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000003404 beta-D-xylosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)CO1)* 0.000 claims description 4
125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
QSDSZOAFLXTJCE-XDNAFOTISA-N (2s,3r,4s,5r)-2-[4-[(4-nitrophenyl)methyl]phenoxy]oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)CO[C@H]1OC(C=C1)=CC=C1CC1=CC=C([N+]([O-])=O)C=C1 QSDSZOAFLXTJCE-XDNAFOTISA-N 0.000 claims 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
125000001488 beta-D-galactosyl group Chemical group C1([C@H](O)[C@@H](O)[C@@H](O)[C@H](O1)CO)* 0.000 claims 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims 1
150000002500 ions Chemical class 0.000 claims 1
-1 alpha -hydroxybenzylphenyl Chemical group 0.000 abstract description 22
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 3
125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 2
125000003277 amino group Chemical group 0.000 abstract 2
230000021736 acetylation Effects 0.000 abstract 1
238000006640 acetylation reaction Methods 0.000 abstract 1
150000008366 benzophenones Chemical class 0.000 abstract 1
CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical group C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 abstract 1
238000002560 therapeutic procedure Methods 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 38
SRBFZHDQGSBBOR-KKQCNMDGSA-N beta-D-xylose Chemical group O[C@@H]1CO[C@@H](O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-KKQCNMDGSA-N 0.000 description 37
239000000047 product Substances 0.000 description 37
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
238000004519 manufacturing process Methods 0.000 description 15
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 12
230000007935 neutral effect Effects 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
239000000460 chlorine Substances 0.000 description 7
230000000871 hypocholesterolemic effect Effects 0.000 description 7
OFQCQIGMURIECL-UHFFFAOYSA-N 2-[2-(diethylamino)ethyl]-2',6'-dimethylspiro[isoquinoline-4,4'-oxane]-1,3-dione;phosphoric acid Chemical compound OP(O)(O)=O.O=C1N(CCN(CC)CC)C(=O)C2=CC=CC=C2C21CC(C)OC(C)C2 OFQCQIGMURIECL-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
230000008859 change Effects 0.000 description 6
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
RYVMUASDIZQXAA-UHFFFAOYSA-N pyranoside Natural products O1C2(OCC(C)C(OC3C(C(O)C(O)C(CO)O3)O)C2)C(C)C(C2(CCC3C4(C)CC5O)C)C1CC2C3CC=C4CC5OC(C(C1O)O)OC(CO)C1OC(C1OC2C(C(OC3C(C(O)C(O)C(CO)O3)O)C(O)C(CO)O2)O)OC(CO)C(O)C1OC1OCC(O)C(O)C1O RYVMUASDIZQXAA-UHFFFAOYSA-N 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
230000000694 effects Effects 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
230000008569 process Effects 0.000 description 4
229920005989 resin Polymers 0.000 description 4
239000011347 resin Substances 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
208000035150 Hypercholesterolemia Diseases 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229920001429 chelating resin Polymers 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000013078 crystal Substances 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
230000000055 hyoplipidemic effect Effects 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
239000006188 syrup Substances 0.000 description 3
235000020357 syrup Nutrition 0.000 description 3
230000001225 therapeutic effect Effects 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
XHVZGMBTQPLORJ-UHFFFAOYSA-N (4-hydroxyphenyl)-(4-methylsulfonylphenyl)methanone Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(=O)C1=CC=C(O)C=C1 XHVZGMBTQPLORJ-UHFFFAOYSA-N 0.000 description 2
125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 description 2
208000031226 Hyperlipidaemia Diseases 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
239000003146 anticoagulant agent Substances 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
125000000188 beta-D-glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 2
235000014633 carbohydrates Nutrition 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
235000012000 cholesterol Nutrition 0.000 description 2
238000003381 deacetylation reaction Methods 0.000 description 2
230000008034 disappearance Effects 0.000 description 2
150000002632 lipids Chemical class 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
229950006780 n-acetylglucosamine Drugs 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
LCLRNQJIZBANOD-UHFFFAOYSA-N (4-hydroxyphenyl)-(4-methylsulfanylphenyl)methanone Chemical compound C1=CC(SC)=CC=C1C(=O)C1=CC=C(O)C=C1 LCLRNQJIZBANOD-UHFFFAOYSA-N 0.000 description 1
MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
241001424309 Arita Species 0.000 description 1
SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical group O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
DUKURNFHYQXCJG-UHFFFAOYSA-N Lewis A pentasaccharide Natural products OC1C(O)C(O)C(C)OC1OC1C(OC2C(C(O)C(O)C(CO)O2)O)C(NC(C)=O)C(OC2C(C(OC3C(OC(O)C(O)C3O)CO)OC(CO)C2O)O)OC1CO DUKURNFHYQXCJG-UHFFFAOYSA-N 0.000 description 1
240000000233 Melia azedarach Species 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
OVRNDRQMDRJTHS-FMDGEEDCSA-N N-acetyl-beta-D-glucosamine Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-FMDGEEDCSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
241000700159 Rattus Species 0.000 description 1
241000700157 Rattus norvegicus Species 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
AVNRQUICFRHQDY-YTWAJWBKSA-N [(3r,4s,5r,6r)-4,5-diacetyloxy-6-bromooxan-3-yl] acetate Chemical compound CC(=O)O[C@@H]1CO[C@H](Br)[C@H](OC(C)=O)[C@H]1OC(C)=O AVNRQUICFRHQDY-YTWAJWBKSA-N 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
230000009471 action Effects 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
230000004931 aggregating effect Effects 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
230000000702 anti-platelet effect Effects 0.000 description 1
239000003529 anticholesteremic agent Substances 0.000 description 1
239000003524 antilipemic agent Substances 0.000 description 1
229960004676 antithrombotic agent Drugs 0.000 description 1
239000003699 antiulcer agent Substances 0.000 description 1
239000003443 antiviral agent Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-FPRJBGLDSA-N beta-D-galactose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-FPRJBGLDSA-N 0.000 description 1
239000012267 brine Substances 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
230000002490 cerebral effect Effects 0.000 description 1
229940126540 compound 41 Drugs 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
230000006196 deacetylation Effects 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
239000000499 gel Substances 0.000 description 1
229960002442 glucosamine Drugs 0.000 description 1
125000003147 glycosyl group Chemical group 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000036571 hydration Effects 0.000 description 1
238000006703 hydration reaction Methods 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
238000011835 investigation Methods 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
231100000636 lethal dose Toxicity 0.000 description 1
RENRQMCACQEWFC-UGKGYDQZSA-N lnp023 Chemical compound C1([C@H]2N(CC=3C=4C=CNC=4C(C)=CC=3OC)CC[C@@H](C2)OCC)=CC=C(C(O)=O)C=C1 RENRQMCACQEWFC-UGKGYDQZSA-N 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
CRGZYKWWYNQGEC-UHFFFAOYSA-N magnesium;methanolate Chemical compound [Mg+2].[O-]C.[O-]C CRGZYKWWYNQGEC-UHFFFAOYSA-N 0.000 description 1
238000010907 mechanical stirring Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
231100001160 nonlethal Toxicity 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
SUGXYMLKALUNIU-UHFFFAOYSA-N silver;imidazol-3-ide Chemical compound [Ag+].C1=C[N-]C=N1 SUGXYMLKALUNIU-UHFFFAOYSA-N 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
238000007711 solidification Methods 0.000 description 1
230000008023 solidification Effects 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000007940 sugar coated tablet Substances 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics

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Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Molecular Biology (AREA)
Genetics & Genomics (AREA)
Biotechnology (AREA)
Biochemistry (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Hematology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Obesity (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Diabetes (AREA)
Bioinformatics & Cheminformatics (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Saccharide Compounds (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)

DD84265446A 1983-07-20 1984-07-19 Procede de preparation de benzyl-phenyl-osides utiles en therapeutique DD224596A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR8311982A FR2549476B1 (fr)	1983-07-20	1983-07-20	Benzyl-phenyl-osides, procede de preparation et utilisation en therapeutique

Publications (1)

Publication Number	Publication Date
DD224596A5 true DD224596A5 (de)	1985-07-10

Family

ID=9290966

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD84265446A DD224596A5 (de)	1983-07-20	1984-07-19	Procede de preparation de benzyl-phenyl-osides utiles en therapeutique

Country Status (17)

Country	Link
US (1)	US4598068A (cs)
EP (1)	EP0133103B1 (cs)
JP (1)	JPS6041691A (cs)
KR (1)	KR910008109B1 (cs)
AT (1)	ATE30726T1 (cs)
CA (1)	CA1226576A (cs)
CS (1)	CS244692B2 (cs)
DD (1)	DD224596A5 (cs)
DE (1)	DE3467349D1 (cs)
DK (1)	DK164556C (cs)
ES (1)	ES534528A0 (cs)
FR (1)	FR2549476B1 (cs)
GR (1)	GR82068B (cs)
HU (1)	HU195835B (cs)
NO (1)	NO157259C (cs)
PT (1)	PT78938B (cs)
ZA (1)	ZA845580B (cs)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2614893B1 (fr) *	1987-05-04	1989-12-22	Fournier Innovation Synergie	Nouveaux b-d-phenyl-thioxylosides, leur procede de preparation et leur application en therapeutique
US4960758A (en) *	1987-05-04	1990-10-02	Fournier Innovation Et Synergie	Novel β-D-phenylthioxylosides, their method of preparation and their use as pharmaceuticals
FR2614894B1 (fr) *	1987-05-06	1989-06-16	Adir	Nouvelles oximes derivees de la tylosine, leur procede de preparation et les compositions pharmaceutiques les contenant
IE63544B1 (en) *	1988-10-18	1995-05-17	Fournier Ind & Sante	Novel Beta-d-phenylthioxylosides their method of preparation and their use in therapy
US5246961A (en) *	1988-10-18	1993-09-21	Fournier Industrie Et Sante	β-d-phenylthioxylosides, and their use as therapeutic agents
DE68907857T2 (de) *	1988-11-03	1993-12-23	Fournier Ind Et Sante Paris	Beta-D-phenylthioxyloside, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel.
FR2652353B1 (fr) *	1989-09-22	1994-02-11	Fournier Industrie Sante	Nouveaux benzopyran-2-one-beta-d-thioxylosides, leur procede de preparation et leur utilisation en therapeutique.
EP0421829B1 (fr) *	1989-09-22	1994-11-09	Fournier Industrie Et Sante	Nouveaux benzopyranone-beta-D-thioxylosides, leur procédé de préparation et leur utilisation en thérapeutique
US6291433B1 (en)	1999-06-11	2001-09-18	Fournier Industrie Et Sante	Derivatives of α-D-Thioxyloside and their use against atheroma
CZ20023023A3 (cs) *	2000-03-17	2003-04-16	Kissei Pharmaceutical Co., Ltd.	Glukopyranosyloxybenzylbenzenové deriváty, léčivé směsi obsahující tyto látky a meziprodukty pro přípravu derivátů
EP1329456B1 (en) *	2000-09-29	2006-08-09	Kissei Pharmaceutical Co., Ltd.	Glucopyranosyloxybenzylbenzene derivatives and medicinal compositions containing the same
CA2429833A1 (en) *	2000-11-30	2002-06-06	Kissei Pharmaceutical Co., Ltd.	Glucopyranosyloxybenzylbenzene derivatives, medicinal compositions containing the same and intermediates in the production thereof
TWI255817B (en) *	2001-02-14	2006-06-01	Kissei Pharmaceutical	Glucopyranosyloxybenzylbenzene derivatives and medicinal use thereof
FR2826368B1 (fr) *	2001-06-21	2004-01-30	Fournier Lab Sa	Nouveaux derives de [4-(4-cyanobenzoyl)phenyl] glycofuranoside, utilisation en tant que medicamment, procede d'obtention et compositions pharmaceutiques les contenant

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL167151C (nl) *	1971-04-09	1981-11-16	Acf Chemiefarma Nv	Werkwijze ter bereiding van geneesmiddelen met anti-parasitaire werking op basis van halogeen bevatten- de 2,2'-methyleendifenolderivaten, alsmede werkwijze ter bereiding van deze geneeskrachtige verbindingen.
FR2492830A1 (fr) *	1980-10-29	1982-04-30	Sori Soc Rech Ind	Nouveaux composes appartenant a la famille des benzoyl- et a-hydroxybenzyl-phenyl-osides, leur procede de preparation et leur application en therapeutique

1983
- 1983-07-20 FR FR8311982A patent/FR2549476B1/fr not_active Expired
1984
- 1984-07-17 EP EP84401496A patent/EP0133103B1/fr not_active Expired
- 1984-07-17 NO NO842916A patent/NO157259C/no unknown
- 1984-07-17 DE DE8484401496T patent/DE3467349D1/de not_active Expired
- 1984-07-17 AT AT84401496T patent/ATE30726T1/de not_active IP Right Cessation
- 1984-07-18 HU HU842794A patent/HU195835B/hu not_active IP Right Cessation
- 1984-07-18 PT PT78938A patent/PT78938B/pt not_active IP Right Cessation
- 1984-07-18 US US06/632,009 patent/US4598068A/en not_active Expired - Fee Related
- 1984-07-19 CA CA000459291A patent/CA1226576A/en not_active Expired
- 1984-07-19 GR GR75362A patent/GR82068B/el unknown
- 1984-07-19 ZA ZA845580A patent/ZA845580B/xx unknown
- 1984-07-19 DK DK353184A patent/DK164556C/da not_active IP Right Cessation
- 1984-07-19 DD DD84265446A patent/DD224596A5/de not_active IP Right Cessation
- 1984-07-19 JP JP59151113A patent/JPS6041691A/ja active Pending
- 1984-07-19 CS CS845568A patent/CS244692B2/cs unknown
- 1984-07-20 KR KR1019840004282A patent/KR910008109B1/ko not_active Expired
- 1984-07-20 ES ES534528A patent/ES534528A0/es active Granted

Also Published As

Publication number	Publication date
DK353184D0 (da)	1984-07-19
DK164556C (da)	1992-12-07
GR82068B (cs)	1984-12-13
DK353184A (da)	1985-01-21
NO157259C (no)	1988-02-17
EP0133103A1 (fr)	1985-02-13
PT78938A (fr)	1984-08-01
ATE30726T1 (de)	1987-11-15
FR2549476A1 (fr)	1985-01-25
EP0133103B1 (fr)	1987-11-11
JPS6041691A (ja)	1985-03-05
NO842916L (no)	1985-01-21
CA1226576A (en)	1987-09-08
ES8505382A1 (es)	1985-05-16
HUT36133A (en)	1985-08-28
DK164556B (da)	1992-07-13
DE3467349D1 (en)	1987-12-17
HU195835B (en)	1988-07-28
KR850001227A (ko)	1985-03-16
NO157259B (no)	1987-11-09
FR2549476B1 (fr)	1986-04-25
ZA845580B (en)	1985-02-27
PT78938B (fr)	1986-06-02
CS244692B2 (en)	1986-08-14
CS556884A2 (en)	1985-09-17
US4598068A (en)	1986-07-01
ES534528A0 (es)	1985-05-16
KR910008109B1 (ko)	1991-10-10

Legal Events

Date	Code	Title
2001-03-29	RPI	Change in the person, name or address of the patentee (searches according to art. 11 and 12 extension act)
2001-05-24	RPI	Change in the person, name or address of the patentee (searches according to art. 11 and 12 extension act)
2002-09-12	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DD224596A5 (de)	1985-07-10	Procede de preparation de benzyl-phenyl-osides utiles en therapeutique
DD202157A5 (de)	1983-08-31	Verfahren zur herstellung einer neuen verbindung aus der familie der benzoyl- und alpha-hydroxybezyl-phenyl-oside
DE2409654A1 (de)	1974-09-12	Therapeutisches mittel
DE1935967C3 (de)	1980-09-25	Naphthacenderivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Zusammensetzungen
DE1811518C3 (de)	1979-05-03	Daunonibicinderivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zusammensetzungen
DE2804099A1 (de)	1978-08-03	Carminomycinderivate, verfahren zu ihrer herstellung und ihre verwendung
DE3443065C2 (cs)	1989-03-23
AT392793B (de)	1991-06-10	Verfahren zur herstellung von neuen anthracyclinglykosiden
DE2502296A1 (de)	1975-09-25	Diaminocyclitol-derivate und verfahren zu ihrer herstellung
DE2422254A1 (de)	1974-11-28	Aminoglycosidderivate und deren salze, verfahren zu deren herstellung und pharmazeutische praeparate
DE2301540A1 (de)	1973-07-19	5-0-(5-amino-5-deoxy-d-pentofuranosyl)n hoch 1-(4-amino-2-hydroxy-butyryl)-4-0(2,6-diamino-2,6-dideoxy-d-gluco-pyranosyl)2-deoxystreptamine
DE2510838A1 (de)	1975-09-18	Neamin-derivate und deren salze, herstellungsverfahren dafuer und pharmazeutische zusammensetzungen
DE2836913A1 (de)	1979-03-15	Desoxyneamine
DE2641388B2 (de)	1980-05-29	3',4'-Didesoxykanamycin B-N-methansulfonsäuren und deren Alkalimetallsalze sowie diese Verbindungen enthaltende pharmazeutische Präparate
DE2365719A1 (de)	1976-01-29	Arabinofuranosyl-6-azacytosine und verfahren zu ihrer herstellung
DE2618009A1 (de)	1976-11-04	1-n-(alpha-hydroxy-omega-aminoacyl)-derivate des 3'-deoxykanamycins a und verfahren zur herstellung derselben
DE2361159C3 (de)	1982-04-29	3'-Desoxy-neamin-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE1770408A1 (de)	1971-10-21	Links-1-n-Butyl-2',6'-Pipecoloxylidid und Verfahren zu seiner Herstellung
DE68928127T2 (de)	1997-09-25	2'-Methylidenpyrimidinnukleosidverbindungen, ihre Verwendung und Verfahren zu ihrer Herstellung
DE69002136T2 (de)	1993-10-14	Saccharidderivate von Protocatechualdehyd.
DE2549921A1 (de)	1976-05-20	Streptaminderivat und dessen salze, ihr herstellungsverfahren sowie pharmazeutische zusammensetzungen
DE3207021A1 (de)	1982-09-23	Aminoacridin-(alpha)- und/oder (beta)-(d)-n-glykosid- und/oder aminoacridin-(alpha)- und/oder (beta)-(l)-n-glykosidderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
CH643831A5 (de)	1984-06-29	Cinnamyl-moranolin-derivate.
DE3905431A1 (de)	1989-09-07	Neue 4-demethyl-4-0-(p-fluorobenzolsulfonyl)anthracyclinglycoside
DE69417907T2 (de)	1999-08-12	Anthracyclin-disaccharide, verfahren zu ihrer herstellung, und diese enthaltende arzneimittel