CS224629B2 - Method for producing new derivates of benzoyl-a alfa-hydroxybenzylphenylglykoside - Google Patents
Method for producing new derivates of benzoyl-a alfa-hydroxybenzylphenylglykoside Download PDFInfo
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- CS224629B2 CS224629B2 CS817961A CS796181A CS224629B2 CS 224629 B2 CS224629 B2 CS 224629B2 CS 817961 A CS817961 A CS 817961A CS 796181 A CS796181 A CS 796181A CS 224629 B2 CS224629 B2 CS 224629B2
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- Czechoslovakia
- Prior art keywords
- group
- beta
- meoh
- steam
- xyl
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- 238000004519 manufacturing process Methods 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 18
- -1 isothiocyano group Chemical group 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 13
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 8
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 150000002367 halogens Chemical class 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 388
- 239000000203 mixture Substances 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 239000011541 reaction mixture Substances 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 9
- 230000003287 optical effect Effects 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- 238000002425 crystallisation Methods 0.000 claims description 6
- 230000008025 crystallization Effects 0.000 claims description 6
- 239000011734 sodium Substances 0.000 claims description 6
- 239000000706 filtrate Substances 0.000 claims description 5
- 238000010992 reflux Methods 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 229930182470 glycoside Natural products 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical class OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 150000002338 glycosides Chemical class 0.000 claims description 3
- 229910052749 magnesium Inorganic materials 0.000 claims description 3
- 239000011777 magnesium Substances 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 230000009467 reduction Effects 0.000 claims description 3
- 229920005989 resin Polymers 0.000 claims description 3
- 239000011347 resin Substances 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- 229910010082 LiAlH Inorganic materials 0.000 claims description 2
- 150000001350 alkyl halides Chemical class 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004436 sodium atom Chemical group 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- BHMLFPOTZYRDKA-IRXDYDNUSA-N (2s)-2-[(s)-(2-iodophenoxy)-phenylmethyl]morpholine Chemical compound IC1=CC=CC=C1O[C@@H](C=1C=CC=CC=1)[C@H]1OCCNC1 BHMLFPOTZYRDKA-IRXDYDNUSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 101100202589 Drosophila melanogaster scrib gene Proteins 0.000 claims 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical group CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims 1
- GIYXAJPCNFJEHY-UHFFFAOYSA-N N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]-1-propanamine hydrochloride (1:1) Chemical compound Cl.C=1C=CC=CC=1C(CCNC)OC1=CC=C(C(F)(F)F)C=C1 GIYXAJPCNFJEHY-UHFFFAOYSA-N 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims 1
- FBUKVWPVBMHYJY-UHFFFAOYSA-N noncarboxylic acid Natural products CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 4
- 125000002252 acyl group Chemical group 0.000 abstract description 2
- 125000003277 amino group Chemical group 0.000 abstract description 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract description 2
- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 abstract description 2
- 125000004429 atom Chemical group 0.000 abstract 5
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 76
- 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 73
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 239000000047 product Substances 0.000 description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 230000008018 melting Effects 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 208000025865 Ulcer Diseases 0.000 description 8
- 230000005764 inhibitory process Effects 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 6
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 6
- 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 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 230000036269 ulceration Effects 0.000 description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 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 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 230000002776 aggregation Effects 0.000 description 3
- 238000004220 aggregation Methods 0.000 description 3
- 230000000141 anti-hypoxic effect Effects 0.000 description 3
- 150000001720 carbohydrates Chemical class 0.000 description 3
- 230000002490 cerebral effect Effects 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
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- 238000007912 intraperitoneal administration Methods 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 229910001923 silver oxide Inorganic materials 0.000 description 3
- 239000001509 sodium citrate Substances 0.000 description 3
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 3
- 230000004083 survival effect Effects 0.000 description 3
- 238000002560 therapeutic procedure Methods 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 2
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 2
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical group O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 206010047249 Venous thrombosis Diseases 0.000 description 2
- 229960001138 acetylsalicylic acid Drugs 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 239000003146 anticoagulant agent Substances 0.000 description 2
- 125000003236 benzoyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
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- 238000005119 centrifugation Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000001640 fractional crystallisation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
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- 230000000704 physical effect Effects 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
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- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- KKWCPKGIYOZPTF-UHFFFAOYSA-N (3-hydroxyphenyl)-[4-(trifluoromethyl)phenyl]methanone Chemical compound OC1=CC=CC(C(=O)C=2C=CC(=CC=2)C(F)(F)F)=C1 KKWCPKGIYOZPTF-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- ZXSQEZNORDWBGZ-UHFFFAOYSA-N 1,3-dihydropyrrolo[2,3-b]pyridin-2-one Chemical compound C1=CN=C2NC(=O)CC2=C1 ZXSQEZNORDWBGZ-UHFFFAOYSA-N 0.000 description 1
- YYUISDWOKJLVMA-UHFFFAOYSA-N 2-propan-2-yl-1h-pyrrole Chemical compound CC(C)C1=CC=CN1 YYUISDWOKJLVMA-UHFFFAOYSA-N 0.000 description 1
- CZMRCDWAGMRECN-UHFFFAOYSA-N 2-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound OCC1OC(CO)(OC2OC(CO)C(O)C(O)C2O)C(O)C1O CZMRCDWAGMRECN-UHFFFAOYSA-N 0.000 description 1
- RTKMFQOHBDVEBC-UHFFFAOYSA-N 3-bromo-3-buten-1-ol Chemical compound OCCC(Br)=C RTKMFQOHBDVEBC-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- 241000490229 Eucephalus Species 0.000 description 1
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
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- 241000700157 Rattus norvegicus Species 0.000 description 1
- 206010040943 Skin Ulcer Diseases 0.000 description 1
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 1
- 208000007536 Thrombosis Diseases 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
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- GRTOGORTSDXSFK-UHFFFAOYSA-N ajmalicine Chemical compound C1=CC=C2C(CCN3CC4C(C)OC=C(C4CC33)C(=O)OC)=C3NC2=C1 GRTOGORTSDXSFK-UHFFFAOYSA-N 0.000 description 1
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- 125000002947 alkylene group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
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- CCGSUNCLSOWKJO-UHFFFAOYSA-N cimetidine Chemical compound N#CNC(=N/C)\NCCSCC1=NC=N[C]1C CCGSUNCLSOWKJO-UHFFFAOYSA-N 0.000 description 1
- 229960001380 cimetidine Drugs 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- GKTWGGQPFAXNFI-HNNXBMFYSA-N clopidogrel Chemical compound C1([C@H](N2CC=3C=CSC=3CC2)C(=O)OC)=CC=CC=C1Cl GKTWGGQPFAXNFI-HNNXBMFYSA-N 0.000 description 1
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
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- 229910052740 iodine Inorganic materials 0.000 description 1
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- 231100000636 lethal dose Toxicity 0.000 description 1
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229940075610 mercuric cyanide Drugs 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012454 non-polar solvent Substances 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
- 150000002905 orthoesters Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- ZLQMRLSBXKQKMG-UHFFFAOYSA-N rauniticine Natural products COC(=O)C1=CC2CC3N(CCc4c3[nH]c5ccccc45)CC2C(C)O1 ZLQMRLSBXKQKMG-UHFFFAOYSA-N 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- LKZMBDSASOBTPN-UHFFFAOYSA-L silver carbonate Substances [Ag].[O-]C([O-])=O LKZMBDSASOBTPN-UHFFFAOYSA-L 0.000 description 1
- 229910001958 silver carbonate Inorganic materials 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 231100000019 skin ulcer Toxicity 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000001732 thrombotic effect Effects 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 230000001562 ulcerogenic effect Effects 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 201000002282 venous insufficiency Diseases 0.000 description 1
- 238000005406 washing Methods 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
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Molecular Biology (AREA)
- Animal Behavior & Ethology (AREA)
- Genetics & Genomics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Biochemistry (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8023133A FR2492830A1 (fr) | 1980-10-29 | 1980-10-29 | Nouveaux composes appartenant a la famille des benzoyl- et a-hydroxybenzyl-phenyl-osides, leur procede de preparation et leur application en therapeutique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS224629B2 true CS224629B2 (en) | 1984-01-16 |
Family
ID=9247461
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS817961A CS224629B2 (en) | 1980-10-29 | 1981-10-29 | Method for producing new derivates of benzoyl-a alfa-hydroxybenzylphenylglykoside |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4432973A (en:Method) |
| EP (1) | EP0051023B1 (en:Method) |
| JP (1) | JPS57102899A (en:Method) |
| KR (1) | KR870001926B1 (en:Method) |
| AT (1) | ATE7701T1 (en:Method) |
| CA (1) | CA1181745A (en:Method) |
| CS (1) | CS224629B2 (en:Method) |
| DD (1) | DD202157A5 (en:Method) |
| DE (1) | DE3163912D1 (en:Method) |
| ES (1) | ES506660A0 (en:Method) |
| FR (1) | FR2492830A1 (en:Method) |
| GR (1) | GR75759B (en:Method) |
| HU (1) | HU191341B (en:Method) |
| ZA (1) | ZA817314B (en:Method) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2549476B1 (fr) * | 1983-07-20 | 1986-04-25 | Rech Ind | Benzyl-phenyl-osides, procede de preparation et utilisation en therapeutique |
| JPS63215688A (ja) * | 1987-03-04 | 1988-09-08 | Jujo Paper Co Ltd | フェノ−ル配糖体の製造法 |
| 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 |
| 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 |
| 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 |
| DK0421829T3 (da) * | 1989-09-22 | 1995-01-16 | Fournier Ind & Sante | Nye benzopyranon-beta-D-thioxylosider, fremgangsmåde til deres fremstilling og deres terapeutiske anvendelse |
| 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. |
| IL140417A0 (en) * | 1998-06-24 | 2002-02-10 | Fournier Ind & Sante | NOVEL COMPOUNDS DERIVED FROM β-D-XYLOSE, PREPARATION METHOD AND THERAPEUTIC USE |
| JP2003500432A (ja) | 1999-06-01 | 2003-01-07 | ザ・ユニバーシティ・オブ・テキサス・サウスウエスタン・メディカル・センター | ジフェニルエーテル誘導体を用いて脱毛症を処置する方法 |
| EP1185232A1 (en) | 1999-06-01 | 2002-03-13 | University Of Texas Southwestern Medical Center | Method of treating hair loss using sulfonyl thyromimetic compounds |
| US6680344B1 (en) | 1999-06-01 | 2004-01-20 | The University Of Texas Southwestern Medical Center | Method of treating hair loss using diphenylmethane derivatives |
| US6291433B1 (en) | 1999-06-11 | 2001-09-18 | Fournier Industrie Et Sante | Derivatives of α-D-Thioxyloside and their use against atheroma |
| FR2802930B1 (fr) * | 1999-12-23 | 2003-10-10 | Fournier Ind & Sante | Benzophenone glycopyranosides, preparation et utilisation en therapeutique |
| FR2802929B1 (fr) * | 1999-12-23 | 2003-06-06 | Fournier Ind & Sante | Benzophenone alpha-d-glycopyranosides, preparation et utilisation en therapeutique |
| EP1286984A2 (en) * | 2000-03-10 | 2003-03-05 | Pharmacia Corporation | Method for the preparation of tetrahydrobenzothiepines |
| FR2826367B1 (fr) * | 2001-06-21 | 2004-01-30 | Fournier Lab Sa | Nouveaux derives de [4-(4-cyanobenzoyl)phenyl] glycopyranoside, utilisation en tant que medicamment, procede d'obtention et compositions pharmaceutiques les contenant |
| 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 |
| FR2860234B1 (fr) | 2003-09-25 | 2005-12-23 | Fournier Lab Sa | Nouveaux derives 666 du thioxylose |
| JP4753022B2 (ja) * | 2004-02-17 | 2011-08-17 | 独立行政法人産業技術総合研究所 | プリオン増殖抑制剤 |
| EP1911738A4 (en) * | 2005-07-29 | 2009-12-16 | Takeda Pharmaceutical | COMPOUND OF PHENOXYALKANOIC ACID |
| FR2903698B1 (fr) | 2006-07-13 | 2009-01-30 | Fournier S A Sa Lab | Nouveaux derives de 5-thioxylopyranose. |
| FR2906248B1 (fr) | 2006-09-27 | 2008-12-26 | Fournier S A Sa Lab | Nouveaux derives de 5-thioxylopyranose |
| FR2906247B1 (fr) | 2006-09-27 | 2008-12-26 | Fournier S A Sa Lab | Nouveaux derives de 5-thioxylopyranose |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2218569A (en) * | 1939-09-13 | 1940-10-22 | Dow Chemical Co | Glycosides of pentose ethers |
| US2798079A (en) * | 1953-12-29 | 1957-07-02 | Universal Oil Prod Co | Condensation of aromatic hydrocarbon derivatives with carbohydrates and related materials |
| US3152115A (en) * | 1960-11-17 | 1964-10-06 | Geigy Chem Corp | New aryl glucosaminides |
| US3356674A (en) * | 1961-07-07 | 1967-12-05 | Rikagaku Kenkyusho | 3-c-hydroxymethyl-3, 5-didesoxy-l-lyxofuranose and its derivatives, and a process for the production thereof |
| US3496196A (en) * | 1965-10-02 | 1970-02-17 | Tanabe Pharm Co Ltd | 4,6-diazido-4,6-dideoxy-myo-inositol tetraacylates |
| FR2141532B1 (en:Method) * | 1971-06-14 | 1974-08-23 | Anvar | |
| US3960835A (en) * | 1974-01-18 | 1976-06-01 | Commercial Solvents Corporation | Zearaline glycoside compounds |
| US4175123A (en) * | 1976-12-23 | 1979-11-20 | Bayer Aktiengesellschaft | Amino-sugar derivatives, process for their preparation and pharmaceutical composition thereof |
-
1980
- 1980-10-29 FR FR8023133A patent/FR2492830A1/fr active Granted
-
1981
- 1981-10-21 AT AT81401654T patent/ATE7701T1/de not_active IP Right Cessation
- 1981-10-21 EP EP81401654A patent/EP0051023B1/fr not_active Expired
- 1981-10-21 DE DE8181401654T patent/DE3163912D1/de not_active Expired
- 1981-10-22 ZA ZA817314A patent/ZA817314B/xx unknown
- 1981-10-22 US US06/314,032 patent/US4432973A/en not_active Expired - Fee Related
- 1981-10-23 GR GR66343A patent/GR75759B/el unknown
- 1981-10-28 ES ES506660A patent/ES506660A0/es active Granted
- 1981-10-28 HU HU813167A patent/HU191341B/hu not_active IP Right Cessation
- 1981-10-29 KR KR1019810004143A patent/KR870001926B1/ko not_active Expired
- 1981-10-29 CS CS817961A patent/CS224629B2/cs unknown
- 1981-10-29 JP JP56172183A patent/JPS57102899A/ja active Granted
- 1981-10-29 DD DD81234458A patent/DD202157A5/de not_active IP Right Cessation
- 1981-10-29 CA CA000389050A patent/CA1181745A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DD202157A5 (de) | 1983-08-31 |
| GR75759B (en:Method) | 1984-08-02 |
| ATE7701T1 (de) | 1984-06-15 |
| JPS57102899A (en) | 1982-06-26 |
| FR2492830A1 (fr) | 1982-04-30 |
| FR2492830B1 (en:Method) | 1983-10-07 |
| ES8302019A1 (es) | 1983-01-01 |
| KR830007485A (ko) | 1983-10-21 |
| JPH024235B2 (en:Method) | 1990-01-26 |
| ZA817314B (en) | 1982-10-27 |
| EP0051023A1 (fr) | 1982-05-05 |
| KR870001926B1 (ko) | 1987-10-22 |
| HU191341B (en) | 1987-02-27 |
| US4432973A (en) | 1984-02-21 |
| CA1181745A (en) | 1985-01-29 |
| ES506660A0 (es) | 1983-01-01 |
| DE3163912D1 (en) | 1984-07-05 |
| EP0051023B1 (fr) | 1984-05-30 |
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