NO118798B - - Google Patents
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- Publication number
- NO118798B NO118798B NO167485A NO16748567A NO118798B NO 118798 B NO118798 B NO 118798B NO 167485 A NO167485 A NO 167485A NO 16748567 A NO16748567 A NO 16748567A NO 118798 B NO118798 B NO 118798B
- Authority
- NO
- Norway
- Prior art keywords
- phenyl
- solution
- ether
- acid
- acetic acid
- Prior art date
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- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 6
- 235000019445 benzyl alcohol Nutrition 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
- 239000012442 inert solvent Substances 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 103
- 239000000243 solution Substances 0.000 description 60
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 30
- -1 n-propyl- Chemical group 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- 239000003208 petroleum Substances 0.000 description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 229910052938 sodium sulfate Inorganic materials 0.000 description 18
- 235000011152 sodium sulphate Nutrition 0.000 description 18
- 238000002844 melting Methods 0.000 description 16
- 230000008018 melting Effects 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 239000000155 melt Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- 235000011121 sodium hydroxide Nutrition 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 235000015497 potassium bicarbonate Nutrition 0.000 description 5
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 5
- 239000011736 potassium bicarbonate Substances 0.000 description 5
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- QGVYHQJBRVSCOP-UHFFFAOYSA-N ClC1=C(C(=CC=C1N1C(CC2=CC(=CC=C12)O)=O)Cl)C Chemical compound ClC1=C(C(=CC=C1N1C(CC2=CC(=CC=C12)O)=O)Cl)C QGVYHQJBRVSCOP-UHFFFAOYSA-N 0.000 description 3
- ZUYBMIXZPDWPGM-UHFFFAOYSA-N ClC1=C(C(=CC=C1N1C(CC2=CC=CC=C12)=O)Cl)C Chemical compound ClC1=C(C(=CC=C1N1C(CC2=CC=CC=C12)=O)Cl)C ZUYBMIXZPDWPGM-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
- 239000007864 aqueous solution Substances 0.000 description 3
- LFKYWVXTNUHXLV-UHFFFAOYSA-N benzyl 2-[2-(2,6-dichloroanilino)phenyl]acetate Chemical compound ClC1=CC=CC(Cl)=C1NC1=CC=CC=C1CC(=O)OCC1=CC=CC=C1 LFKYWVXTNUHXLV-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- JCICIFOYVSPMHG-UHFFFAOYSA-N 1-(2,6-dichlorophenyl)-3h-indol-2-one Chemical compound ClC1=CC=CC(Cl)=C1N1C2=CC=CC=C2CC1=O JCICIFOYVSPMHG-UHFFFAOYSA-N 0.000 description 2
- SLPAPGNFCSVQKP-UHFFFAOYSA-N 2,6-dichloro-3-methyl-n-phenylaniline Chemical compound CC1=CC=C(Cl)C(NC=2C=CC=CC=2)=C1Cl SLPAPGNFCSVQKP-UHFFFAOYSA-N 0.000 description 2
- HDUUZPLYVVQTKN-UHFFFAOYSA-N 2,6-dichloro-n-phenylaniline Chemical compound ClC1=CC=CC(Cl)=C1NC1=CC=CC=C1 HDUUZPLYVVQTKN-UHFFFAOYSA-N 0.000 description 2
- ICJTVRXTYOYEOT-UHFFFAOYSA-N 2-[2-(2,6-dimethylanilino)phenyl]acetic acid Chemical compound CC1=CC=CC(C)=C1NC1=CC=CC=C1CC(O)=O ICJTVRXTYOYEOT-UHFFFAOYSA-N 0.000 description 2
- MWPZLYLEVLUDNL-UHFFFAOYSA-N 2-[2-(3-chloro-2-methylanilino)phenyl]acetic acid Chemical compound CC1=C(Cl)C=CC=C1NC1=CC=CC=C1CC(O)=O MWPZLYLEVLUDNL-UHFFFAOYSA-N 0.000 description 2
- YGASORODGQFDEQ-UHFFFAOYSA-N 5-bromo-1-(2,6-dichlorophenyl)-3H-indol-2-one Chemical compound ClC1=C(C(=CC=C1)Cl)N1C(CC2=CC(=CC=C12)Br)=O YGASORODGQFDEQ-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 208000025747 Rheumatic disease Diseases 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 230000001741 anti-phlogistic effect Effects 0.000 description 2
- 230000002917 arthritic effect Effects 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 2
- YPBCAMNSNFVYQL-UHFFFAOYSA-N ethyl 2-[2-(2,6-dichloroanilino)phenyl]acetate Chemical compound CCOC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl YPBCAMNSNFVYQL-UHFFFAOYSA-N 0.000 description 2
- NLQDHKUVSQNWOE-UHFFFAOYSA-N ethyl 2-[2-(2,6-dimethylanilino)phenyl]acetate Chemical compound C(C)OC(CC1=C(C=CC=C1)NC=1C(=CC=CC1C)C)=O NLQDHKUVSQNWOE-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 208000027866 inflammatory disease Diseases 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- QQZIEVCMENSZDZ-UHFFFAOYSA-N methyl 2-[2-(3-chloro-2-methylanilino)phenyl]acetate Chemical compound COC(=O)CC1=CC=CC=C1NC1=CC=CC(Cl)=C1C QQZIEVCMENSZDZ-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000000552 rheumatic effect Effects 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- KEXFRBIOHPDZQM-UHFFFAOYSA-N 1,1-bis(2,2-dimethylpropoxy)-n,n-dimethylmethanamine Chemical compound CC(C)(C)COC(N(C)C)OCC(C)(C)C KEXFRBIOHPDZQM-UHFFFAOYSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- CDUSVSOBGRHHRW-UHFFFAOYSA-N 2,6-dichloro-N-(4-chlorophenyl)-3-methylaniline Chemical compound ClC1=CC=C(C=C1)NC1=C(C(=CC=C1Cl)C)Cl CDUSVSOBGRHHRW-UHFFFAOYSA-N 0.000 description 1
- BXWHARZUIVTCNE-UHFFFAOYSA-N 2,6-dichloro-N-(4-methoxyphenyl)-3-methylaniline Chemical compound ClC1=C(NC2=CC=C(C=C2)OC)C(=CC=C1C)Cl BXWHARZUIVTCNE-UHFFFAOYSA-N 0.000 description 1
- QMBFJLTXYWWQIQ-UHFFFAOYSA-N 2-[2-(2,3-dimethylanilino)phenyl]acetic acid Chemical compound CC1=CC=CC(NC=2C(=CC=CC=2)CC(O)=O)=C1C QMBFJLTXYWWQIQ-UHFFFAOYSA-N 0.000 description 1
- CNQCAFDKWBMIJV-UHFFFAOYSA-N 2-[2-(2,4-dichloro-3-methylanilino)phenyl]acetic acid Chemical compound CC1=C(Cl)C=CC(NC=2C(=CC=CC=2)CC(O)=O)=C1Cl CNQCAFDKWBMIJV-UHFFFAOYSA-N 0.000 description 1
- UNGMVTOHNYXHSO-UHFFFAOYSA-N 2-[5-bromo-2-(2,6-dichloroanilino)phenyl]acetic acid Chemical compound ClC1=C(NC2=C(C=C(C=C2)Br)CC(=O)O)C(=CC=C1)Cl UNGMVTOHNYXHSO-UHFFFAOYSA-N 0.000 description 1
- NWTKDJYRLPOOFM-UHFFFAOYSA-N 2-[5-chloro-2-(2,6-dichloroanilino)phenyl]acetic acid Chemical compound OC(=O)CC1=CC(Cl)=CC=C1NC1=C(Cl)C=CC=C1Cl NWTKDJYRLPOOFM-UHFFFAOYSA-N 0.000 description 1
- BPEUHDIEZQWRGC-UHFFFAOYSA-N 2-chloro-n-(2,6-dichlorophenyl)-n-phenylacetamide Chemical compound ClC=1C=CC=C(Cl)C=1N(C(=O)CCl)C1=CC=CC=C1 BPEUHDIEZQWRGC-UHFFFAOYSA-N 0.000 description 1
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- QJPJQTDYNZXKQF-UHFFFAOYSA-N 4-bromoanisole Chemical compound COC1=CC=C(Br)C=C1 QJPJQTDYNZXKQF-UHFFFAOYSA-N 0.000 description 1
- USSXQFVQXWYFNE-UHFFFAOYSA-N 5-chloro-1-(2,6-dichlorophenyl)-3H-indol-2-one Chemical compound ClC1=C(C(=CC=C1)Cl)N1C(CC2=CC(=CC=C12)Cl)=O USSXQFVQXWYFNE-UHFFFAOYSA-N 0.000 description 1
- YRLCJTLJODVGRC-UHFFFAOYSA-N COC1=CC=C(C=C1C)NC1=C(C=CC=C1)CC(=O)O Chemical compound COC1=CC=C(C=C1C)NC1=C(C=CC=C1)CC(=O)O YRLCJTLJODVGRC-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- BRMMYSYZPGSKMH-UHFFFAOYSA-N ClC1=C(C(=CC=C1N1C(CC2=CC(=CC=C12)Cl)=O)Cl)C Chemical compound ClC1=C(C(=CC=C1N1C(CC2=CC(=CC=C12)Cl)=O)Cl)C BRMMYSYZPGSKMH-UHFFFAOYSA-N 0.000 description 1
- UEWCIIKUNOIZBM-UHFFFAOYSA-N ClC1=C(C(=CC=C1N1C(CC2=CC(=CC=C12)OC)=O)Cl)C Chemical compound ClC1=C(C(=CC=C1N1C(CC2=CC(=CC=C12)OC)=O)Cl)C UEWCIIKUNOIZBM-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- 206010015150 Erythema Diseases 0.000 description 1
- 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
- SBDNJUWAMKYJOX-UHFFFAOYSA-N Meclofenamic Acid Chemical compound CC1=CC=C(Cl)C(NC=2C(=CC=CC=2)C(O)=O)=C1Cl SBDNJUWAMKYJOX-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- PFOJFRFNLWMZCO-UHFFFAOYSA-N ethyl 2-[2-(2,4-dichloro-3-methylanilino)-5-methoxyphenyl]acetate Chemical compound C(C)OC(CC1=C(C=CC(=C1)OC)NC=1C(=C(C(=CC1)Cl)C)Cl)=O PFOJFRFNLWMZCO-UHFFFAOYSA-N 0.000 description 1
- OSJFFTVNMXAXTD-UHFFFAOYSA-N ethyl 2-[5-chloro-2-(2,4-dichloro-3-methylanilino)phenyl]acetate Chemical compound C(C)OC(CC1=C(C=CC(=C1)Cl)NC=1C(=C(C(=CC1)Cl)C)Cl)=O OSJFFTVNMXAXTD-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 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
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- HGYGJANXKMHORB-UHFFFAOYSA-N methyl 2-[2-(2,3-dimethylanilino)phenyl]acetate Chemical compound COC(CC1=C(C=CC=C1)NC1=C(C(=CC=C1)C)C)=O HGYGJANXKMHORB-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- WKSKHBFEWVRZEZ-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-n-phenylacetamide Chemical compound ClC=1C=CC=C(Cl)C=1N(C(=O)C)C1=CC=CC=C1 WKSKHBFEWVRZEZ-UHFFFAOYSA-N 0.000 description 1
- DWVWVSLAIJHBBG-UHFFFAOYSA-N n-(2,6-dichlorophenyl)acetamide Chemical compound CC(=O)NC1=C(Cl)C=CC=C1Cl DWVWVSLAIJHBBG-UHFFFAOYSA-N 0.000 description 1
- 239000003883 ointment base Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/38—Oxygen atoms in positions 2 and 3, e.g. isatin
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH462666A CH473769A (de) | 1966-03-30 | 1966-03-30 | Verfahren zur Herstellung von neuen substituierten Phenylessigsäureestern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO118798B true NO118798B (pl) | 1970-02-16 |
Family
ID=4279632
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO167485A NO118798B (pl) | 1966-03-30 | 1967-03-29 |
Country Status (15)
| Country | Link |
|---|---|
| AT (1) | AT271455B (pl) |
| BE (1) | BE696248A (pl) |
| CH (1) | CH473769A (pl) |
| DE (1) | DE1618465C3 (pl) |
| DK (1) | DK137325B (pl) |
| ES (1) | ES338638A1 (pl) |
| FI (1) | FI46501C (pl) |
| FR (2) | FR1517251A (pl) |
| GB (1) | GB1132318A (pl) |
| GR (1) | GR36365B (pl) |
| IL (1) | IL27708A (pl) |
| NL (2) | NL6704484A (pl) |
| NO (1) | NO118798B (pl) |
| SE (1) | SE346307B (pl) |
| YU (1) | YU32041B (pl) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2068397A2 (en) * | 1969-10-06 | 1971-08-27 | Geigy Ag J R | Methyl 2-(6-chloro-o-toluidino) phenylacetate antirheumatic |
| JPS549240A (en) * | 1977-06-23 | 1979-01-24 | Asahi Chem Ind Co Ltd | New derivative of phenylglycolic acid, its preparation and analgesic and antiinflammatory agent contining it as effective component |
| IT1097265B (it) * | 1978-06-23 | 1985-08-31 | Acraf | Nouva sintesi di un acido fenilacetico |
| ES520813A0 (es) * | 1983-03-21 | 1984-05-16 | Prodes Sa | Procedimiento para la obtencion del ester del acido 2-(2,6-diclorofenil)amino bencenoacetico con acido glicolico. |
| JPS6028957A (ja) * | 1983-07-27 | 1985-02-14 | Kaken Pharmaceut Co Ltd | インドリル酢酸およびフエニル酢酸のエステル誘導体およびその製造法 |
| EP0380712B1 (de) * | 1989-01-27 | 1995-01-04 | HEUMANN PHARMA GMBH & CO | Verfahren zur Herstellung von 2,6-Dichlordiphenylaminessigsäurederivaten |
| ITMI20012434A1 (it) | 2001-11-20 | 2003-05-20 | Dompe Spa | Acidi 2-aril-propionici e composizioni farmaceutiche che li contengono |
| WO2009007827A2 (en) * | 2007-07-10 | 2009-01-15 | Chemisches Institut Schaefer Ag | Novel diclofenac esters and uses thereof |
| WO2014006529A2 (en) * | 2012-07-03 | 2014-01-09 | Mahesh Kandula | Compositions and methods for the treatment of moderate to severe pain |
-
0
- NL NL137301D patent/NL137301C/xx active
-
1966
- 1966-03-30 CH CH462666A patent/CH473769A/de not_active IP Right Cessation
-
1967
- 1967-03-28 FI FI670878A patent/FI46501C/fi active
- 1967-03-29 GB GB14261/67A patent/GB1132318A/en not_active Expired
- 1967-03-29 BE BE696248D patent/BE696248A/xx not_active IP Right Cessation
- 1967-03-29 NL NL6704484A patent/NL6704484A/xx unknown
- 1967-03-29 SE SE4283/67A patent/SE346307B/xx unknown
- 1967-03-29 GR GR670136365A patent/GR36365B/el unknown
- 1967-03-29 FR FR100667A patent/FR1517251A/fr not_active Expired
- 1967-03-29 DK DK164667AA patent/DK137325B/da not_active IP Right Cessation
- 1967-03-29 YU YU0612/67A patent/YU32041B/xx unknown
- 1967-03-29 IL IL27708A patent/IL27708A/en unknown
- 1967-03-29 AT AT299567A patent/AT271455B/de active
- 1967-03-29 DE DE1618465A patent/DE1618465C3/de not_active Expired
- 1967-03-29 ES ES338638A patent/ES338638A1/es not_active Expired
- 1967-03-29 NO NO167485A patent/NO118798B/no unknown
- 1967-06-27 FR FR112053A patent/FR6680M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE1618465C3 (de) | 1979-05-31 |
| SE346307B (pl) | 1972-07-03 |
| BE696248A (pl) | 1967-09-29 |
| FI46501C (fi) | 1973-04-10 |
| CH473769A (de) | 1969-06-15 |
| YU61267A (en) | 1973-08-31 |
| DE1618465A1 (de) | 1971-05-27 |
| NL6704484A (pl) | 1967-10-02 |
| NL137301C (pl) | |
| AT271455B (de) | 1969-06-10 |
| DE1618465B2 (de) | 1978-09-28 |
| FI46501B (fi) | 1973-01-02 |
| DK137325C (pl) | 1978-07-17 |
| GR36365B (el) | 1969-02-04 |
| YU32041B (en) | 1974-02-28 |
| FR6680M (pl) | 1969-02-03 |
| ES338638A1 (es) | 1968-07-01 |
| DK137325B (da) | 1978-02-20 |
| IL27708A (en) | 1971-01-28 |
| FR1517251A (fr) | 1968-03-15 |
| GB1132318A (en) | 1968-10-30 |
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