DE1543639B2 - Verfahren zur herstellung von substituierten phenylessigsaeuren und deren salzen sowie genannte verbindungen enthaltende pharmazeutische zusammensetzungen - Google Patents
Verfahren zur herstellung von substituierten phenylessigsaeuren und deren salzen sowie genannte verbindungen enthaltende pharmazeutische zusammensetzungenInfo
- Publication number
- DE1543639B2 DE1543639B2 DE1966G0046553 DEG0046553A DE1543639B2 DE 1543639 B2 DE1543639 B2 DE 1543639B2 DE 1966G0046553 DE1966G0046553 DE 1966G0046553 DE G0046553 A DEG0046553 A DE G0046553A DE 1543639 B2 DE1543639 B2 DE 1543639B2
- Authority
- DE
- Germany
- Prior art keywords
- solution
- ether
- torr
- water
- dichloro
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 title description 17
- 239000008194 pharmaceutical composition Substances 0.000 title description 3
- FWEOQOXTVHGIFQ-UHFFFAOYSA-N 8-anilinonaphthalene-1-sulfonic acid Chemical class C=12C(S(=O)(=O)O)=CC=CC2=CC=CC=1NC1=CC=CC=C1 FWEOQOXTVHGIFQ-UHFFFAOYSA-N 0.000 title 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 167
- 239000000243 solution Substances 0.000 description 99
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 50
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 49
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 47
- -1 alkoxy radical Chemical class 0.000 description 39
- 239000003208 petroleum Substances 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 25
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 23
- 229910052938 sodium sulfate Inorganic materials 0.000 description 22
- 235000011152 sodium sulphate Nutrition 0.000 description 22
- 235000019445 benzyl alcohol Nutrition 0.000 description 20
- 239000003921 oil Substances 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 18
- DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 description 17
- 150000003839 salts Chemical class 0.000 description 17
- 239000000155 melt Substances 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 8
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 206010042674 Swelling Diseases 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 150000007530 organic bases Chemical class 0.000 description 6
- 239000003279 phenylacetic acid Substances 0.000 description 6
- 229960003424 phenylacetic acid Drugs 0.000 description 6
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 6
- 235000015497 potassium bicarbonate Nutrition 0.000 description 6
- 239000011736 potassium bicarbonate Substances 0.000 description 6
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 230000008961 swelling Effects 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 5
- 150000007529 inorganic bases Chemical class 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- GZRAEWKMFPWXNW-UHFFFAOYSA-N 2-[2-(2,6-dichloro-3-methylanilino)phenyl]acetic acid Chemical compound CC1=CC=C(Cl)C(NC=2C(=CC=CC=2)CC(O)=O)=C1Cl GZRAEWKMFPWXNW-UHFFFAOYSA-N 0.000 description 4
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- RIZZNPRPQGBKQW-UHFFFAOYSA-N FC(C=1C=C(NC2=C(C=CC=C2)CC(=O)O)C=CC1)(F)F Chemical compound FC(C=1C=C(NC2=C(C=CC=C2)CC(=O)O)C=CC1)(F)F RIZZNPRPQGBKQW-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 4
- 239000012346 acetyl chloride Substances 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 230000003110 anti-inflammatory effect Effects 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 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 4
- 239000012280 lithium aluminium hydride Substances 0.000 description 4
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- VETACGBDFVVKGZ-UHFFFAOYSA-N methyl 2-[2-(2,6-dichloroanilino)phenyl]acetate Chemical compound COC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl VETACGBDFVVKGZ-UHFFFAOYSA-N 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 4
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 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 3
- 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 3
- AWNWLZIGTUDXIU-UHFFFAOYSA-N 2-[2-[2-chloro-5-(trifluoromethyl)anilino]phenyl]acetic acid Chemical compound ClC1=C(NC2=C(C=CC=C2)CC(=O)O)C=C(C=C1)C(F)(F)F AWNWLZIGTUDXIU-UHFFFAOYSA-N 0.000 description 3
- ACEYWLASKHAWSF-UHFFFAOYSA-N 2-[2-[2-chloro-5-(trifluoromethyl)anilino]phenyl]acetonitrile Chemical compound ClC1=C(NC2=C(C=CC=C2)CC#N)C=C(C=C1)C(F)(F)F ACEYWLASKHAWSF-UHFFFAOYSA-N 0.000 description 3
- ZEDYGCYCIALGBA-UHFFFAOYSA-N 2-chloro-N-[2-(chloromethyl)phenyl]-5-(trifluoromethyl)aniline Chemical compound ClC1=C(NC2=C(CCl)C=CC=C2)C=C(C=C1)C(F)(F)F ZEDYGCYCIALGBA-UHFFFAOYSA-N 0.000 description 3
- 229920002261 Corn starch Polymers 0.000 description 3
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- 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 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
- AVJVMGRZWCTART-UHFFFAOYSA-N N-[2-(chloromethyl)phenyl]-N-[3-(trifluoromethyl)phenyl]acetamide Chemical compound C(C)(=O)N(C1=CC(=CC=C1)C(F)(F)F)C1=C(CCl)C=CC=C1 AVJVMGRZWCTART-UHFFFAOYSA-N 0.000 description 3
- 206010030113 Oedema Diseases 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000008120 corn starch Substances 0.000 description 3
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000008273 gelatin Substances 0.000 description 3
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- 238000007327 hydrogenolysis reaction Methods 0.000 description 3
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- QARVLSVVCXYDNA-UHFFFAOYSA-N phenyl bromide Natural products BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
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- 239000000600 sorbitol Substances 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- WRHBGCGVWNFMEU-UHFFFAOYSA-N 1-(2,6-dichloro-3-methylphenyl)-3h-indol-2-one Chemical compound CC1=CC=C(Cl)C(N2C3=CC=CC=C3CC2=O)=C1Cl WRHBGCGVWNFMEU-UHFFFAOYSA-N 0.000 description 2
- KEVGMTXZSZSSKH-UHFFFAOYSA-N 1-(2,6-dichloro-3-methylphenyl)-5-hydroxy-3H-indol-2-one Chemical compound ClC1=C(C(=CC=C1C)Cl)N1C(CC2=CC(=CC=C12)O)=O KEVGMTXZSZSSKH-UHFFFAOYSA-N 0.000 description 2
- AYVZXDFCFQSWJD-UHFFFAOYSA-N 2,6-dichloro-3-methylaniline Chemical compound CC1=CC=C(Cl)C(N)=C1Cl AYVZXDFCFQSWJD-UHFFFAOYSA-N 0.000 description 2
- 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 2
- CKVPEUHEFGGHKC-UHFFFAOYSA-N 2,6-dichloro-n-(4-chlorophenyl)aniline Chemical compound C1=CC(Cl)=CC=C1NC1=C(Cl)C=CC=C1Cl CKVPEUHEFGGHKC-UHFFFAOYSA-N 0.000 description 2
- VAFJNGRSQFDQDD-UHFFFAOYSA-N 2,6-dichloro-n-[2-(chloromethyl)phenyl]aniline Chemical compound ClCC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl VAFJNGRSQFDQDD-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
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- 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 2
- SZGCZUHNLAGTAE-UHFFFAOYSA-N 2-chloro-n-(2,6-dichloro-3-methylphenyl)-n-phenylacetamide Chemical compound CC1=CC=C(Cl)C(N(C(=O)CCl)C=2C=CC=CC=2)=C1Cl SZGCZUHNLAGTAE-UHFFFAOYSA-N 0.000 description 2
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
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- LGPYQJLODAIFLY-UHFFFAOYSA-N N-[2-(chloromethyl)phenyl]-2,6-dimethylaniline Chemical compound CC1=C(NC2=C(CCl)C=CC=C2)C(=CC=C1)C LGPYQJLODAIFLY-UHFFFAOYSA-N 0.000 description 2
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- 235000021355 Stearic acid Nutrition 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 230000002917 arthritic effect Effects 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 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 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
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- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- YEZNLOUZAIOMLT-UHFFFAOYSA-N tolfenamic acid Chemical compound CC1=C(Cl)C=CC=C1NC1=CC=CC=C1C(O)=O YEZNLOUZAIOMLT-UHFFFAOYSA-N 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 230000001960 triggered effect Effects 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH496165A CH460804A (de) | 1965-04-08 | 1965-04-08 | Verfahren zur Herstellung von neuen substituierten Phenylessigsäuren |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1543639A1 DE1543639A1 (de) | 1970-02-05 |
| DE1543639B2 true DE1543639B2 (de) | 1977-02-24 |
Family
ID=4285534
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1966G0046553 Granted DE1543639B2 (de) | 1965-04-08 | 1966-04-07 | Verfahren zur herstellung von substituierten phenylessigsaeuren und deren salzen sowie genannte verbindungen enthaltende pharmazeutische zusammensetzungen |
Country Status (16)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2751224A1 (de) * | 1977-06-23 | 1979-01-04 | Asahi Chemical Ind | Neue substituierte phenylglykolsaeure, ihre ester und salze, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittelzubereitungen |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3513199A (en) * | 1967-05-05 | 1970-05-19 | Smithkline Corp | Substituted anilino benzyl alcohols |
| CH506480A (de) * | 1969-02-20 | 1971-04-30 | Ciba Geigy Ag | Verfahren zur Herstellung von neuen, substituierten o-Anilino-phenäthylalkoholen |
| JPS58194814A (ja) * | 1982-05-11 | 1983-11-12 | Nippon Shinyaku Co Ltd | 免疫調節作用を有する薬剤 |
| US5237070A (en) * | 1985-07-22 | 1993-08-17 | Riker Laboratories, Inc. | Substituted DI-t-butylphenols |
| ZA865090B (en) * | 1985-07-22 | 1988-02-24 | Riker Laboratories Inc | Substituted di-t-butylphenols |
| DE3623193A1 (de) * | 1986-07-10 | 1988-01-14 | Gruenenthal Gmbh | Neue verbindungen, diese enthaltende arzneimittel und verfahren zu deren herstellung |
| ES2011588A6 (es) * | 1989-05-29 | 1990-01-16 | Vinas Lab | Procedimiento para la preparacion de un nuevo derivado fenilacetico. |
| EP0405602A1 (en) * | 1989-06-30 | 1991-01-02 | Laboratorios Vinas S.A. | New Zinc derivatives of anti-inflammatory drugs having improved therapeutic activity |
| IT1256345B (it) * | 1992-08-20 | 1995-12-01 | Esteri nitrici di derivati dell'acido 2-(2,6-di-alo-fenilammino) fenilacetico e procedimento per la loro preparazione | |
| US6355680B1 (en) | 1996-02-20 | 2002-03-12 | Exocell, Inc. | Albumin-binding compounds that prevent nonenzymatic glycation and that may be used for treatment of glycation-related pathologies |
| AR061623A1 (es) | 2006-06-26 | 2008-09-10 | Novartis Ag | Derivados de acido fenilacetico |
| CN114516813B (zh) | 2022-02-25 | 2024-05-28 | 复旦大学 | 一种双氯芬酸钠的连续流制备方法 |
| CN114539086B (zh) | 2022-02-25 | 2023-10-03 | 复旦大学 | 一种双氯芬酸钠的合成方法 |
-
0
- NL NL133740D patent/NL133740C/xx active
-
1965
- 1965-04-08 CH CH496165A patent/CH460804A/de unknown
- 1965-04-08 FR FR57111A patent/FR1487352A/fr not_active Expired
-
1966
- 1966-04-06 FI FI660898A patent/FI44619C/fi active
- 1966-04-06 DK DK180566AA patent/DK117639B/da unknown
- 1966-04-06 ES ES0325271A patent/ES325271A1/es not_active Expired
- 1966-04-06 NO NO162524A patent/NO120793B/no unknown
- 1966-04-06 ES ES0325270A patent/ES325270A1/es not_active Expired
- 1966-04-07 AT AT619567A patent/AT262982B/de active
- 1966-04-07 GB GB15497/66A patent/GB1139332A/en not_active Expired
- 1966-04-07 AT AT619667A patent/AT262983B/de active
- 1966-04-07 IL IL25545A patent/IL25545A/en unknown
- 1966-04-07 SE SE4833/66A patent/SE322527B/xx unknown
- 1966-04-07 NL NL6604752A patent/NL6604752A/xx unknown
- 1966-04-07 AT AT619767A patent/AT266096B/de active
- 1966-04-07 AT AT334966A patent/AT263755B/de active
- 1966-04-07 DE DE1966G0046553 patent/DE1543639B2/de active Granted
- 1966-04-08 BE BE679315D patent/BE679315A/xx not_active IP Right Cessation
- 1966-07-06 FR FR68443A patent/FR5524M/fr not_active Expired
-
1972
- 1972-04-19 CY CY63772A patent/CY637A/xx unknown
- 1972-12-31 MY MY1972118A patent/MY7200118A/xx unknown
-
1977
- 1977-11-21 DO DO1977002615A patent/DOP1977002615A/es unknown
- 1977-12-09 DO DO1977002614A patent/DOP1977002614A/es unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2751224A1 (de) * | 1977-06-23 | 1979-01-04 | Asahi Chemical Ind | Neue substituierte phenylglykolsaeure, ihre ester und salze, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittelzubereitungen |
Also Published As
| Publication number | Publication date |
|---|---|
| BE679315A (enrdf_load_stackoverflow) | 1966-10-10 |
| SE322527B (enrdf_load_stackoverflow) | 1970-04-13 |
| CY637A (en) | 1972-04-19 |
| FR1487352A (fr) | 1967-07-07 |
| AT262983B (de) | 1968-07-10 |
| FI44619C (fi) | 1971-12-10 |
| NO120793B (enrdf_load_stackoverflow) | 1970-12-07 |
| GB1139332A (en) | 1969-01-08 |
| NL6604752A (enrdf_load_stackoverflow) | 1966-10-10 |
| DOP1977002615A (es) | 1983-05-27 |
| DK117639B (da) | 1970-05-19 |
| DE1793592A1 (de) | 1972-04-20 |
| DE1543639A1 (de) | 1970-02-05 |
| NL133740C (enrdf_load_stackoverflow) | |
| FR5524M (enrdf_load_stackoverflow) | 1967-11-06 |
| FI44619B (enrdf_load_stackoverflow) | 1971-08-31 |
| DOP1977002614A (es) | 1983-05-27 |
| IL25545A (en) | 1970-07-19 |
| DE1793592B2 (de) | 1977-06-16 |
| AT263755B (de) | 1968-08-12 |
| AT262982B (de) | 1968-07-10 |
| ES325270A1 (es) | 1967-04-01 |
| AT266096B (de) | 1968-11-11 |
| ES325271A1 (es) | 1967-04-01 |
| CH460804A (de) | 1968-08-15 |
| MY7200118A (en) | 1972-12-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 |