NO780648L - Fremgangsmaate til fremstilling av nye aryl-heksafuranosider - Google Patents

Fremgangsmaate til fremstilling av nye aryl-heksafuranosider

Info

Publication number: NO780648L
Authority: NO; Norway
Prior art keywords: phenyl; benzyl; xylo; hydrogen; ethyl
Prior art date: 1977-02-25

Application number

NO780648A

Other languages

English (en)

Norwegian (no)

Inventor

Jean M J Tronchet

Bruno Baehler

Alberto Rossi

Gerhard Baschang

Alex Sele

Original Assignee

Ciba Geigy Ag

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.)

1977-02-25

Filing date

1978-02-24

Publication date

1978-08-28

1978-02-24 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1978-08-28 Publication of NO780648L publication Critical patent/NO780648L/no

Links

238000000034 method Methods 0.000 title claims description 61
-1 trifluoromethylphenyl Chemical group 0.000 claims description 162
150000001875 compounds Chemical class 0.000 claims description 96
239000001257 hydrogen Substances 0.000 claims description 75
229910052739 hydrogen Inorganic materials 0.000 claims description 75
125000000217 alkyl group Chemical group 0.000 claims description 62
150000002431 hydrogen Chemical class 0.000 claims description 50
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 47
125000003118 aryl group Chemical group 0.000 claims description 36
239000000203 mixture Substances 0.000 claims description 33
230000003287 optical effect Effects 0.000 claims description 33
238000006243 chemical reaction Methods 0.000 claims description 32
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
125000001118 alkylidene group Chemical group 0.000 claims description 27
125000002252 acyl group Chemical group 0.000 claims description 26
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
125000003545 alkoxy group Chemical group 0.000 claims description 24
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 23
150000003839 salts Chemical class 0.000 claims description 23
239000004593 Epoxy Substances 0.000 claims description 22
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
125000001589 carboacyl group Chemical group 0.000 claims description 19
125000004432 carbon atom Chemical group C* 0.000 claims description 19
239000007858 starting material Substances 0.000 claims description 19
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 18
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 17
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 15
239000004305 biphenyl Substances 0.000 claims description 12
235000010290 biphenyl Nutrition 0.000 claims description 12
125000006267 biphenyl group Chemical group 0.000 claims description 12
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 12
125000003282 alkyl amino group Chemical group 0.000 claims description 11
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
229910052751 metal Inorganic materials 0.000 claims description 11
239000002184 metal Substances 0.000 claims description 11
125000001424 substituent group Chemical group 0.000 claims description 11
230000003110 anti-inflammatory effect Effects 0.000 claims description 10
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 10
PFBUKDPBVNJDEW-UHFFFAOYSA-N dichlorocarbene Chemical group Cl[C]Cl PFBUKDPBVNJDEW-UHFFFAOYSA-N 0.000 claims description 10
125000005843 halogen group Chemical group 0.000 claims description 10
125000000068 chlorophenyl group Chemical group 0.000 claims description 9
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
239000000825 pharmaceutical preparation Substances 0.000 claims description 9
125000006493 trifluoromethyl benzyl group Chemical group 0.000 claims description 9
125000003342 alkenyl group Chemical group 0.000 claims description 8
125000004803 chlorobenzyl group Chemical group 0.000 claims description 8
125000005400 pyridylcarbonyl group Chemical group N1=C(C=CC=C1)C(=O)* 0.000 claims description 8
125000000753 cycloalkyl group Chemical group 0.000 claims description 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
125000004799 bromophenyl group Chemical group 0.000 claims description 6
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 claims description 6
230000000737 periodic effect Effects 0.000 claims description 6
125000003944 tolyl group Chemical group 0.000 claims description 6
125000005036 alkoxyphenyl group Chemical group 0.000 claims description 5
125000005037 alkyl phenyl group Chemical group 0.000 claims description 5
125000003435 aroyl group Chemical group 0.000 claims description 5
125000004429 atom Chemical group 0.000 claims description 5
125000006278 bromobenzyl group Chemical group 0.000 claims description 5
FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical group BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 claims description 5
125000005059 halophenyl group Chemical group 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
125000006178 methyl benzyl group Chemical group 0.000 claims description 5
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 5
239000000126 substance Substances 0.000 claims description 5
125000006307 alkoxy benzyl group Chemical group 0.000 claims description 4
125000006177 alkyl benzyl group Chemical group 0.000 claims description 4
230000015572 biosynthetic process Effects 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
238000003776 cleavage reaction Methods 0.000 claims description 3
125000006277 halobenzyl group Chemical group 0.000 claims description 3
230000007017 scission Effects 0.000 claims description 3
125000003541 2-chlorobenzoyl group Chemical group ClC1=C(C(=O)*)C=CC=C1 0.000 claims description 2
125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 2
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
125000006331 halo benzoyl group Chemical group 0.000 claims 2
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 171
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 129
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 107
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 92
239000000243 solution Substances 0.000 description 89
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 88
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 65
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 54
229960001701 chloroform Drugs 0.000 description 54
239000002253 acid Substances 0.000 description 52
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 48
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 46
239000000741 silica gel Substances 0.000 description 46
229910002027 silica gel Inorganic materials 0.000 description 46
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
235000019441 ethanol Nutrition 0.000 description 34
238000004809 thin layer chromatography Methods 0.000 description 31
235000019439 ethyl acetate Nutrition 0.000 description 29
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 27
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 23
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
239000011541 reaction mixture Substances 0.000 description 20
150000007513 acids Chemical class 0.000 description 19
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
235000011121 sodium hydroxide Nutrition 0.000 description 18
239000003921 oil Substances 0.000 description 15
235000019198 oils Nutrition 0.000 description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 13
229910052943 magnesium sulfate Inorganic materials 0.000 description 13
235000019341 magnesium sulphate Nutrition 0.000 description 13
238000003756 stirring Methods 0.000 description 13
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 12
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
239000012071 phase Substances 0.000 description 12
239000002904 solvent Substances 0.000 description 12
229910052783 alkali metal Inorganic materials 0.000 description 11
238000001704 evaporation Methods 0.000 description 11
230000008020 evaporation Effects 0.000 description 11
229910052736 halogen Inorganic materials 0.000 description 11
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 11
229910000041 hydrogen chloride Inorganic materials 0.000 description 11
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
238000004440 column chromatography Methods 0.000 description 10
229910052740 iodine Inorganic materials 0.000 description 10
239000000047 product Substances 0.000 description 10
238000010992 reflux Methods 0.000 description 10
229910052938 sodium sulfate Inorganic materials 0.000 description 10
235000011152 sodium sulphate Nutrition 0.000 description 10
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 9
239000000460 chlorine Substances 0.000 description 9
229910052801 chlorine Inorganic materials 0.000 description 9
239000013078 crystal Substances 0.000 description 9
238000002425 crystallisation Methods 0.000 description 9
230000008025 crystallization Effects 0.000 description 9
150000002367 halogens Chemical class 0.000 description 9
230000007935 neutral effect Effects 0.000 description 9
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
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 8
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
229960000583 acetic acid Drugs 0.000 description 8
150000001335 aliphatic alkanes Chemical class 0.000 description 8
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
229910052794 bromium Inorganic materials 0.000 description 8
239000006185 dispersion Substances 0.000 description 8
239000003456 ion exchange resin Substances 0.000 description 8
229920003303 ion-exchange polymer Polymers 0.000 description 8
229910052708 sodium Inorganic materials 0.000 description 8
239000011734 sodium Substances 0.000 description 8
239000012312 sodium hydride Substances 0.000 description 8
229910000104 sodium hydride Inorganic materials 0.000 description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
150000001340 alkali metals Chemical class 0.000 description 7
239000008346 aqueous phase Substances 0.000 description 7
239000003054 catalyst Substances 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
238000001035 drying Methods 0.000 description 7
229910052744 lithium Inorganic materials 0.000 description 7
229920006395 saturated elastomer Polymers 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
230000002378 acidificating effect Effects 0.000 description 6
150000005215 alkyl ethers Chemical class 0.000 description 6
239000002585 base Substances 0.000 description 6
238000001816 cooling Methods 0.000 description 6
230000007717 exclusion Effects 0.000 description 6
HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 6
229940098779 methanesulfonic acid Drugs 0.000 description 6
239000012299 nitrogen atmosphere Substances 0.000 description 6
239000003208 petroleum Substances 0.000 description 6
238000000746 purification Methods 0.000 description 6
239000000725 suspension Substances 0.000 description 6
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
125000004423 acyloxy group Chemical group 0.000 description 5
150000008044 alkali metal hydroxides Chemical class 0.000 description 5
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
239000003480 eluent Substances 0.000 description 5
239000011261 inert gas Substances 0.000 description 5
229910052500 inorganic mineral Inorganic materials 0.000 description 5
235000010755 mineral Nutrition 0.000 description 5
239000011707 mineral Substances 0.000 description 5
239000011591 potassium Substances 0.000 description 5
229910052700 potassium Inorganic materials 0.000 description 5
229960003975 potassium Drugs 0.000 description 5
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 4
FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 4
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
239000013543 active substance Substances 0.000 description 4
150000003973 alkyl amines Chemical class 0.000 description 4
230000000202 analgesic effect Effects 0.000 description 4
150000008064 anhydrides Chemical class 0.000 description 4
229910052786 argon Inorganic materials 0.000 description 4
239000012298 atmosphere Substances 0.000 description 4
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 4
239000002775 capsule Substances 0.000 description 4
238000007872 degassing Methods 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
239000005457 ice water Substances 0.000 description 4
239000012442 inert solvent Substances 0.000 description 4
239000011630 iodine Substances 0.000 description 4
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
125000001624 naphthyl group Chemical group 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 4
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
239000006188 syrup Substances 0.000 description 4
235000020357 syrup Nutrition 0.000 description 4
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
241000206607 Porphyra umbilicalis Species 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
229910001854 alkali hydroxide Inorganic materials 0.000 description 3
229910000147 aluminium phosphate Inorganic materials 0.000 description 3
239000000730 antalgic agent Substances 0.000 description 3
RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 3
229940092714 benzenesulfonic acid Drugs 0.000 description 3
USFRYJRPHFMVBZ-UHFFFAOYSA-M benzyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 USFRYJRPHFMVBZ-UHFFFAOYSA-M 0.000 description 3
238000009835 boiling Methods 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000012230 colorless oil Substances 0.000 description 3
229910052802 copper Inorganic materials 0.000 description 3
239000010949 copper Substances 0.000 description 3
150000004292 cyclic ethers Chemical class 0.000 description 3
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
NZZFYRREKKOMAT-UHFFFAOYSA-N diiodomethane Chemical compound ICI NZZFYRREKKOMAT-UHFFFAOYSA-N 0.000 description 3
238000010828 elution Methods 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
239000000284 extract Substances 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000011777 magnesium Substances 0.000 description 3
150000007522 mineralic acids Chemical class 0.000 description 3
229910052763 palladium Inorganic materials 0.000 description 3
229920001467 poly(styrenesulfonates) Polymers 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
238000009849 vacuum degassing Methods 0.000 description 3
RAHOAHBOOHXRDY-UHFFFAOYSA-M (4-chlorophenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].C1=CC(Cl)=CC=C1C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 RAHOAHBOOHXRDY-UHFFFAOYSA-M 0.000 description 2
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
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125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
FNIATMYXUPOJRW-UHFFFAOYSA-N cyclohexylidene Chemical group [C]1CCCCC1 FNIATMYXUPOJRW-UHFFFAOYSA-N 0.000 description 1
HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
PWAPCRSSMCLZHG-UHFFFAOYSA-N cyclopentylidene Chemical group [C]1CCCC1 PWAPCRSSMCLZHG-UHFFFAOYSA-N 0.000 description 1
150000001983 dialkylethers Chemical class 0.000 description 1
150000008049 diazo compounds Chemical class 0.000 description 1
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
239000008298 dragée Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
125000003700 epoxy group Chemical group 0.000 description 1
125000005949 ethanesulfonyloxy group Chemical group 0.000 description 1
CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
BUDBHJPMAKXMLD-UHFFFAOYSA-N ethyl 6-methyl-2-phenylquinoline-4-carboxylate Chemical compound N=1C2=CC=C(C)C=C2C(C(=O)OCC)=CC=1C1=CC=CC=C1 BUDBHJPMAKXMLD-UHFFFAOYSA-N 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
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LPEPZBJOKDYZAD-UHFFFAOYSA-N flufenamic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=CC=CC(C(F)(F)F)=C1 LPEPZBJOKDYZAD-UHFFFAOYSA-N 0.000 description 1
ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
239000000499 gel Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
GWOFUCIGLDBNKM-UHFFFAOYSA-N glafenine Chemical compound OCC(O)COC(=O)C1=CC=CC=C1NC1=CC=NC2=CC(Cl)=CC=C12 GWOFUCIGLDBNKM-UHFFFAOYSA-N 0.000 description 1
229960001650 glafenine Drugs 0.000 description 1
LTYRAPJYLUPLCI-UHFFFAOYSA-N glycolonitrile Chemical compound OCC#N LTYRAPJYLUPLCI-UHFFFAOYSA-N 0.000 description 1
238000005469 granulation Methods 0.000 description 1
230000003179 granulation Effects 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229940083761 high-ceiling diuretics pyrazolone derivative Drugs 0.000 description 1
229960001340 histamine Drugs 0.000 description 1
229910000043 hydrogen iodide Inorganic materials 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
229940071870 hydroiodic acid Drugs 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
CYWFCPPBTWOZSF-UHFFFAOYSA-N ibufenac Chemical compound CC(C)CC1=CC=C(CC(O)=O)C=C1 CYWFCPPBTWOZSF-UHFFFAOYSA-N 0.000 description 1
229950009183 ibufenac Drugs 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
210000000936 intestine Anatomy 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
LGYTZKPVOAIUKX-UHFFFAOYSA-N kebuzone Chemical compound O=C1C(CCC(=O)C)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 LGYTZKPVOAIUKX-UHFFFAOYSA-N 0.000 description 1
229960000194 kebuzone Drugs 0.000 description 1
150000002561 ketenes Chemical class 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
239000008101 lactose Substances 0.000 description 1
231100001231 less toxic Toxicity 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
229960003803 meclofenamic acid Drugs 0.000 description 1
229960003464 mefenamic acid Drugs 0.000 description 1
HYYBABOKPJLUIN-UHFFFAOYSA-N mefenamic acid Chemical compound CC1=CC=CC(NC=2C(=CC=CC=2)C(O)=O)=C1C HYYBABOKPJLUIN-UHFFFAOYSA-N 0.000 description 1
MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 1
229910000000 metal hydroxide Inorganic materials 0.000 description 1
150000004692 metal hydroxides Chemical class 0.000 description 1
DJGAAPFSPWAYTJ-UHFFFAOYSA-M metamizole sodium Chemical compound [Na+].O=C1C(N(CS([O-])(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 DJGAAPFSPWAYTJ-UHFFFAOYSA-M 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
OOGNFQMTGRZRAB-UHFFFAOYSA-N morazone Chemical compound CC1C(C=2C=CC=CC=2)OCCN1CC(C1=O)=C(C)N(C)N1C1=CC=CC=C1 OOGNFQMTGRZRAB-UHFFFAOYSA-N 0.000 description 1
229960004610 morazone Drugs 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
229950002805 naftypramide Drugs 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
235000001968 nicotinic acid Nutrition 0.000 description 1
229960003512 nicotinic acid Drugs 0.000 description 1
239000011664 nicotinic acid Substances 0.000 description 1
229960000916 niflumic acid Drugs 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
239000002674 ointment Substances 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
150000004967 organic peroxy acids Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
150000002913 oxalic acids Chemical class 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
229960000649 oxyphenbutazone Drugs 0.000 description 1
HFHZKZSRXITVMK-UHFFFAOYSA-N oxyphenbutazone Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=C(O)C=C1 HFHZKZSRXITVMK-UHFFFAOYSA-N 0.000 description 1
GHZNWXGYWUBLLI-UHFFFAOYSA-N p-Lactophenetide Chemical compound CCOC1=CC=C(NC(=O)C(C)O)C=C1 GHZNWXGYWUBLLI-UHFFFAOYSA-N 0.000 description 1
WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229960003893 phenacetin Drugs 0.000 description 1
229960005222 phenazone Drugs 0.000 description 1
229960002895 phenylbutazone Drugs 0.000 description 1
VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
229940096825 phenylmercury Drugs 0.000 description 1
DCNLOVYDMCVNRZ-UHFFFAOYSA-N phenylmercury(.) Chemical compound [Hg]C1=CC=CC=C1 DCNLOVYDMCVNRZ-UHFFFAOYSA-N 0.000 description 1
125000004437 phosphorous atom Chemical group 0.000 description 1
150000003017 phosphorus Chemical group 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
239000006187 pill Substances 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
239000012286 potassium permanganate Substances 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
229960002189 propyphenazone Drugs 0.000 description 1
PXWLVJLKJGVOKE-UHFFFAOYSA-N propyphenazone Chemical compound O=C1C(C(C)C)=C(C)N(C)N1C1=CC=CC=C1 PXWLVJLKJGVOKE-UHFFFAOYSA-N 0.000 description 1
JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
DNTVKOMHCDKATN-UHFFFAOYSA-N pyrazolidine-3,5-dione Chemical compound O=C1CC(=O)NN1 DNTVKOMHCDKATN-UHFFFAOYSA-N 0.000 description 1
ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
150000003248 quinolines Chemical class 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
229950000385 ramifenazone Drugs 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229940100890 silver compound Drugs 0.000 description 1
150000003379 silver compounds Chemical class 0.000 description 1
229910001023 sodium amalgam Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000001119 stannous chloride Substances 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
229950000244 sulfanilic acid Drugs 0.000 description 1
229960003329 sulfinpyrazone Drugs 0.000 description 1
MBGGBVCUIVRRBF-UHFFFAOYSA-N sulfinpyrazone Chemical compound O=C1N(C=2C=CC=CC=2)N(C=2C=CC=CC=2)C(=O)C1CCS(=O)C1=CC=CC=C1 MBGGBVCUIVRRBF-UHFFFAOYSA-N 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000000829 suppository Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
238000010998 test method Methods 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
229940099259 vaseline Drugs 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
239000002578 wasp venom Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 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
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]

Landscapes

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)
Medicinal Chemistry (AREA)
Biotechnology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Molecular Biology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Genetics & Genomics (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
Biochemistry (AREA)
Pain & Pain Management (AREA)
Pharmacology & Pharmacy (AREA)
Crystallography & Structural Chemistry (AREA)
Rheumatology (AREA)
Bioinformatics & Cheminformatics (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NO780648A 1977-02-25 1978-02-24 Fremgangsmaate til fremstilling av nye aryl-heksafuranosider NO780648L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH239677		1977-02-25

Publications (1)

Publication Number	Publication Date
NO780648L true NO780648L (no)	1978-08-28

Family

ID=4232791

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO780648A NO780648L (no)	1977-02-25	1978-02-24	Fremgangsmaate til fremstilling av nye aryl-heksafuranosider

Country Status (18)

Country	Link
US (1)	US4192868A (da)
JP (1)	JPS53121732A (da)
AU (1)	AU3355078A (da)
BE (1)	BE864290A (da)
DD (1)	DD135390A5 (da)
DE (1)	DE2807306A1 (da)
DK (1)	DK83778A (da)
ES (1)	ES467259A1 (da)
FI (1)	FI780594A7 (da)
FR (1)	FR2381786A1 (da)
GB (1)	GB1584925A (da)
IL (1)	IL54121A0 (da)
IT (1)	IT7848157A0 (da)
NL (1)	NL7802105A (da)
NO (1)	NO780648L (da)
NZ (1)	NZ186558A (da)
SE (1)	SE7802107L (da)
ZA (1)	ZA781103B (da)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5358936A (en) *	1990-08-03	1994-10-25	Paul Gordon	Anionic furanose derivatives, methods of making and using the same
US5367062A (en) *	1992-08-21	1994-11-22	Medicarb Inc.	Disubstituted and deoxydisubstituted derivatives of α-d-lyxofuranosides having anti-inflammatory and anti-proliferative activity
ATE238804T1 (de) *	1993-06-11	2003-05-15	Boston Life Sciences Inc	Immunomodulierende, entzündungshemmende und antiproliferative verbindungen:5,6-dideoxy, 5- aminoderivate von idose und 6-deoxy, 6- aminoderivate von glukose
EP1085913A1 (en)	1998-06-08	2001-03-28	Ferris Corporation	Analgesic and antinociceptive methods

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH539032A (de) *	1969-07-03	1973-07-15	Ciba Geigy Ag	Verfahren zur Herstellung von Hexafuranoseverbindungen
IL37955A0 (en) *	1970-11-13	1971-12-29	Ciba Geigy Ag	O-esters of monosaccharides,their manufacture and pharmaceutical compositions containing them
US3978041A (en) *	1972-12-22	1976-08-31	Ciba-Geigy Corporation	Phenoxy substituted glycosides

1978
- 1978-02-21 DE DE19782807306 patent/DE2807306A1/de not_active Withdrawn
- 1978-02-22 FR FR7805080A patent/FR2381786A1/fr not_active Withdrawn
- 1978-02-22 FI FI780594A patent/FI780594A7/fi not_active Application Discontinuation
- 1978-02-22 US US05/880,255 patent/US4192868A/en not_active Expired - Lifetime
- 1978-02-23 IL IL54121A patent/IL54121A0/xx unknown
- 1978-02-23 ES ES467259A patent/ES467259A1/es not_active Expired
- 1978-02-23 GB GB7286/78A patent/GB1584925A/en not_active Expired
- 1978-02-23 DD DD78203825A patent/DD135390A5/xx unknown
- 1978-02-23 AU AU33550/78A patent/AU3355078A/en active Pending
- 1978-02-23 SE SE7802107A patent/SE7802107L/xx unknown
- 1978-02-23 IT IT7848157A patent/IT7848157A0/it unknown
- 1978-02-24 NO NO780648A patent/NO780648L/no unknown
- 1978-02-24 NL NL7802105A patent/NL7802105A/xx not_active Application Discontinuation
- 1978-02-24 NZ NZ186558A patent/NZ186558A/xx unknown
- 1978-02-24 BE BE185452A patent/BE864290A/xx unknown
- 1978-02-24 DK DK83778A patent/DK83778A/da unknown
- 1978-02-25 JP JP2041478A patent/JPS53121732A/ja active Pending
- 1978-12-18 ZA ZA00781103A patent/ZA781103B/xx unknown

Also Published As

Publication number	Publication date
DE2807306A1 (de)	1978-08-31
IT7848157A0 (it)	1978-02-23
BE864290A (fr)	1978-08-24
US4192868A (en)	1980-03-11
FI780594A7 (fi)	1978-08-26
FR2381786A1 (fr)	1978-09-22
ES467259A1 (es)	1978-10-16
ZA781103B (en)	1979-01-31
NZ186558A (en)	1980-02-21
JPS53121732A (en)	1978-10-24
AU3355078A (en)	1979-08-30
DK83778A (da)	1978-08-26
NL7802105A (nl)	1978-08-29
SE7802107L (sv)	1978-08-26
GB1584925A (en)	1981-02-18
DD135390A5 (de)	1979-05-02
IL54121A0 (en)	1978-04-30

Publication	Publication Date	Title
US3654349A (en)	1972-04-04	Substituted indenyl acetic acids
KR20020028878A (ko)	2002-04-17	신규한 인터루킨-1 및 종양사멸인자-α의 조절인자들,상기 조절인자들의 합성 및 상기 조절인자들의 사용 방법
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