JPH0153266B2 - - Google Patents
Info
- Publication number
- JPH0153266B2 JPH0153266B2 JP56023638A JP2363881A JPH0153266B2 JP H0153266 B2 JPH0153266 B2 JP H0153266B2 JP 56023638 A JP56023638 A JP 56023638A JP 2363881 A JP2363881 A JP 2363881A JP H0153266 B2 JPH0153266 B2 JP H0153266B2
- Authority
- JP
- Japan
- Prior art keywords
- amino
- mol
- solution
- added
- phenyl
- 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.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims description 25
- -1 sodium 2-amino-3-[hydroxy(4-chlorophenyl)methyl]phenyl acetate hydrate Chemical compound 0.000 claims description 25
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 150000001768 cations Chemical class 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 claims description 3
- 229940049953 phenylacetate Drugs 0.000 claims description 3
- AAAYAHLNKYKTKK-UHFFFAOYSA-N 2-[2-amino-5-chloro-3-[hydroxy(phenyl)methyl]phenyl]acetic acid Chemical compound NC1=C(C=C(C=C1C(C1=CC=CC=C1)O)Cl)CC(=O)O AAAYAHLNKYKTKK-UHFFFAOYSA-N 0.000 claims description 2
- SSEGXOGUAIJRJE-UHFFFAOYSA-N O.NC1=C(C=CC=C1C(C1=CC=CC=C1)O)CC(=O)O Chemical compound O.NC1=C(C=CC=C1C(C1=CC=CC=C1)O)CC(=O)O SSEGXOGUAIJRJE-UHFFFAOYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims 1
- HSFQBFMEWSTNOW-UHFFFAOYSA-N sodium;carbanide Chemical group [CH3-].[Na+] HSFQBFMEWSTNOW-UHFFFAOYSA-N 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 78
- 239000000243 solution Substances 0.000 description 41
- 238000004519 manufacturing process Methods 0.000 description 33
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
- 238000004458 analytical method Methods 0.000 description 28
- 239000000203 mixture Substances 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- 229910001868 water Inorganic materials 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- 125000000217 alkyl group Chemical group 0.000 description 17
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- 239000004480 active ingredient Substances 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 239000007788 liquid Substances 0.000 description 14
- 238000003756 stirring Methods 0.000 description 13
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 8
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
- 239000002775 capsule Substances 0.000 description 8
- 235000019441 ethanol Nutrition 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 239000008101 lactose Substances 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 description 5
- SULMNCIGVRMBIU-UHFFFAOYSA-N 2-[2-amino-3-[hydroxy(phenyl)methyl]phenyl]acetic acid Chemical compound NC1=C(CC(O)=O)C=CC=C1C(O)C1=CC=CC=C1 SULMNCIGVRMBIU-UHFFFAOYSA-N 0.000 description 5
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- 229920002472 Starch Polymers 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000008107 starch Substances 0.000 description 5
- 235000019698 starch Nutrition 0.000 description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000004677 hydrates Chemical class 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- KJRCEJOSASVSRA-UHFFFAOYSA-N propane-2-thiol Chemical compound CC(C)S KJRCEJOSASVSRA-UHFFFAOYSA-N 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-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
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- OJEGAMHXVWSGDH-UHFFFAOYSA-N n-methyl-2-methylsulfanylacetamide Chemical compound CNC(=O)CSC OJEGAMHXVWSGDH-UHFFFAOYSA-N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- XJDQUPFWVIUWNZ-UHFFFAOYSA-N o-ethyl propanethioate Chemical compound CCOC(=S)CC XJDQUPFWVIUWNZ-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000008174 sterile solution Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- AETYKGYTWDBKKL-UHFFFAOYSA-N 2-[2-amino-3-(2,4-dichlorobenzoyl)phenyl]-2-phenylsulfanylacetamide Chemical compound C=1C=CC(C(=O)C=2C(=CC(Cl)=CC=2)Cl)=C(N)C=1C(C(=O)N)SC1=CC=CC=C1 AETYKGYTWDBKKL-UHFFFAOYSA-N 0.000 description 2
- ZLSSJIOMMQAYDS-UHFFFAOYSA-N 2-[2-amino-3-(2,4-difluorobenzoyl)phenyl]-2-phenylsulfanylacetamide Chemical compound C=1C=CC(C(=O)C=2C(=CC(F)=CC=2)F)=C(N)C=1C(C(=O)N)SC1=CC=CC=C1 ZLSSJIOMMQAYDS-UHFFFAOYSA-N 0.000 description 2
- HMVMESHNQFQHDZ-UHFFFAOYSA-N 2-[2-amino-3-(2-fluorobenzoyl)phenyl]-2-phenylsulfanylacetamide Chemical compound C=1C=CC(C(=O)C=2C(=CC=CC=2)F)=C(N)C=1C(C(=O)N)SC1=CC=CC=C1 HMVMESHNQFQHDZ-UHFFFAOYSA-N 0.000 description 2
- CJXBHFANXQMZBF-UHFFFAOYSA-N 2-phenylethanethioamide Chemical compound NC(=S)CC1=CC=CC=C1 CJXBHFANXQMZBF-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- DULCUDSUACXJJC-UHFFFAOYSA-N benzeneacetic acid ethyl ester Natural products CCOC(=O)CC1=CC=CC=C1 DULCUDSUACXJJC-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 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
- 239000001506 calcium phosphate Substances 0.000 description 2
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 2
- 235000013539 calcium stearate Nutrition 0.000 description 2
- 239000008116 calcium stearate Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 235000008504 concentrate Nutrition 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 229940099112 cornstarch Drugs 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 2
- 229940038472 dicalcium phosphate Drugs 0.000 description 2
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 235000001727 glucose Nutrition 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- LYDAHNXGYJRKLL-UHFFFAOYSA-N n,n-dimethyl-2-methylsulfanylacetamide Chemical compound CSCC(=O)N(C)C LYDAHNXGYJRKLL-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- JCPSDGBPFXACKB-UHFFFAOYSA-N (2-amino-3-chlorophenyl)-phenylmethanone Chemical compound NC1=C(Cl)C=CC=C1C(=O)C1=CC=CC=C1 JCPSDGBPFXACKB-UHFFFAOYSA-N 0.000 description 1
- ZUWXHHBROGLWNH-UHFFFAOYSA-N (2-amino-5-chlorophenyl)-phenylmethanone Chemical compound NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 ZUWXHHBROGLWNH-UHFFFAOYSA-N 0.000 description 1
- LFMHZYLLULKEAM-UHFFFAOYSA-N (2-aminophenyl)-(2,4-difluorophenyl)methanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=C(F)C=C1F LFMHZYLLULKEAM-UHFFFAOYSA-N 0.000 description 1
- NRAJMXHXQHCBHO-UHFFFAOYSA-N (2-aminophenyl)-(2-fluorophenyl)methanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=CC=C1F NRAJMXHXQHCBHO-UHFFFAOYSA-N 0.000 description 1
- FFFXIQFESQNINT-UHFFFAOYSA-N (2-aminophenyl)-(4-fluorophenyl)methanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=C(F)C=C1 FFFXIQFESQNINT-UHFFFAOYSA-N 0.000 description 1
- WJDPHVJEFVAKMT-UHFFFAOYSA-N (2-aminophenyl)-[4-(trifluoromethyl)phenyl]methanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=C(C(F)(F)F)C=C1 WJDPHVJEFVAKMT-UHFFFAOYSA-N 0.000 description 1
- KYWXRBNOYGGPIZ-UHFFFAOYSA-N 1-morpholin-4-ylethanone Chemical compound CC(=O)N1CCOCC1 KYWXRBNOYGGPIZ-UHFFFAOYSA-N 0.000 description 1
- DQAGOEKCOUPTFB-UHFFFAOYSA-N 2-(2-amino-3-benzoyl-5-chlorophenyl)-n-methyl-2-methylsulfanylacetamide Chemical compound CNC(=O)C(SC)C1=CC(Cl)=CC(C(=O)C=2C=CC=CC=2)=C1N DQAGOEKCOUPTFB-UHFFFAOYSA-N 0.000 description 1
- JZTNRIZCEQXHCX-UHFFFAOYSA-N 2-(2-amino-3-benzoyl-5-chlorophenyl)-n-methylacetamide Chemical compound CNC(=O)CC1=CC(Cl)=CC(C(=O)C=2C=CC=CC=2)=C1N JZTNRIZCEQXHCX-UHFFFAOYSA-N 0.000 description 1
- ZDPDBTKMOHMUCZ-UHFFFAOYSA-N 2-(2-amino-3-benzoylphenyl)-1-morpholin-4-ylethanone Chemical compound C1=CC=C(C(=O)C=2C=CC=CC=2)C(N)=C1CC(=O)N1CCOCC1 ZDPDBTKMOHMUCZ-UHFFFAOYSA-N 0.000 description 1
- FPRGALQPEHLMNK-UHFFFAOYSA-N 2-(2-amino-3-benzoylphenyl)-2-methylsulfanylacetamide Chemical compound CSC(C(N)=O)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1N FPRGALQPEHLMNK-UHFFFAOYSA-N 0.000 description 1
- SUMXHTAHXORDBD-UHFFFAOYSA-N 2-(2-amino-3-benzoylphenyl)-n,n-dimethyl-2-methylsulfanylacetamide Chemical compound CN(C)C(=O)C(SC)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1N SUMXHTAHXORDBD-UHFFFAOYSA-N 0.000 description 1
- RKFHYQGDKLNMOQ-UHFFFAOYSA-N 2-(2-amino-3-benzoylphenyl)-n-methyl-2-methylsulfanylacetamide Chemical compound CNC(=O)C(SC)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1N RKFHYQGDKLNMOQ-UHFFFAOYSA-N 0.000 description 1
- YHZANKPQPBORBP-UHFFFAOYSA-N 2-(4-chlorophenyl)sulfanylacetamide Chemical compound NC(=O)CSC1=CC=C(Cl)C=C1 YHZANKPQPBORBP-UHFFFAOYSA-N 0.000 description 1
- HSKTWHGUQYMEDV-UHFFFAOYSA-N 2-[2-amino-3-(2,4-dichlorobenzoyl)phenyl]acetamide Chemical compound NC(=O)CC1=CC=CC(C(=O)C=2C(=CC(Cl)=CC=2)Cl)=C1N HSKTWHGUQYMEDV-UHFFFAOYSA-N 0.000 description 1
- CQHPOZQTVGWMBK-UHFFFAOYSA-N 2-[2-amino-3-(2,4-difluorobenzoyl)phenyl]acetamide Chemical compound NC(=O)CC1=CC=CC(C(=O)C=2C(=CC(F)=CC=2)F)=C1N CQHPOZQTVGWMBK-UHFFFAOYSA-N 0.000 description 1
- QYWOBAQCODTFCM-UHFFFAOYSA-N 2-[2-amino-3-(4-chlorobenzoyl)phenyl]acetamide Chemical compound NC(=O)CC1=CC=CC(C(=O)C=2C=CC(Cl)=CC=2)=C1N QYWOBAQCODTFCM-UHFFFAOYSA-N 0.000 description 1
- PVARPHBOLNOERP-UHFFFAOYSA-N 2-[2-amino-3-(4-fluorobenzoyl)phenyl]-2-propylsulfanylacetamide Chemical compound CCCSC(C(N)=O)C1=CC=CC(C(=O)C=2C=CC(F)=CC=2)=C1N PVARPHBOLNOERP-UHFFFAOYSA-N 0.000 description 1
- XAARRDGAECXQPW-UHFFFAOYSA-N 2-[2-amino-3-(4-fluorobenzoyl)phenyl]acetamide Chemical compound NC(=O)CC1=CC=CC(C(=O)C=2C=CC(F)=CC=2)=C1N XAARRDGAECXQPW-UHFFFAOYSA-N 0.000 description 1
- VUMFVUKYSQDAJD-UHFFFAOYSA-N 2-[2-amino-3-[(4-chlorophenyl)-hydroxymethyl]phenyl]acetic acid Chemical compound NC1=C(CC(O)=O)C=CC=C1C(O)C1=CC=C(Cl)C=C1 VUMFVUKYSQDAJD-UHFFFAOYSA-N 0.000 description 1
- GOBICNVZBJRNAZ-UHFFFAOYSA-N 2-[2-amino-3-[4-(trifluoromethyl)benzoyl]phenyl]-2-phenylsulfanylacetamide Chemical compound C=1C=CC(C(=O)C=2C=CC(=CC=2)C(F)(F)F)=C(N)C=1C(C(=O)N)SC1=CC=CC=C1 GOBICNVZBJRNAZ-UHFFFAOYSA-N 0.000 description 1
- LPYKIKWWPFNVKP-UHFFFAOYSA-N 2-[2-amino-3-[4-(trifluoromethyl)benzoyl]phenyl]acetamide Chemical compound NC(=O)CC1=CC=CC(C(=O)C=2C=CC(=CC=2)C(F)(F)F)=C1N LPYKIKWWPFNVKP-UHFFFAOYSA-N 0.000 description 1
- QKICJZJTTGUDBP-UHFFFAOYSA-N 2-[3-benzoyl-2-(dimethylamino)phenyl]acetamide Chemical compound CN(C)C1=C(CC(N)=O)C=CC=C1C(=O)C1=CC=CC=C1 QKICJZJTTGUDBP-UHFFFAOYSA-N 0.000 description 1
- QIINHZUDBRVEDD-UHFFFAOYSA-N 2-[3-benzoyl-2-(methylamino)phenyl]acetamide Chemical compound CNC1=C(CC(N)=O)C=CC=C1C(=O)C1=CC=CC=C1 QIINHZUDBRVEDD-UHFFFAOYSA-N 0.000 description 1
- KIYRSYYOVDHSPG-UHFFFAOYSA-N 2-amino-2-phenylacetamide Chemical class NC(=O)C(N)C1=CC=CC=C1 KIYRSYYOVDHSPG-UHFFFAOYSA-N 0.000 description 1
- OBENGAMZEGRSIC-UHFFFAOYSA-N 2-methylsulfanylacetamide Chemical compound CSCC(N)=O OBENGAMZEGRSIC-UHFFFAOYSA-N 0.000 description 1
- VDZLYEWXIUYNSS-UHFFFAOYSA-N 2-phenyl-2-phenylsulfanylacetamide Chemical compound C=1C=CC=CC=1C(C(=O)N)SC1=CC=CC=C1 VDZLYEWXIUYNSS-UHFFFAOYSA-N 0.000 description 1
- CFEVRAOHOOLAOR-UHFFFAOYSA-N 2-phenyl-2-propylsulfanylacetamide Chemical compound CCCSC(C(N)=O)C1=CC=CC=C1 CFEVRAOHOOLAOR-UHFFFAOYSA-N 0.000 description 1
- KBRJQEVSKVOLNR-UHFFFAOYSA-N 2-phenylsulfanylacetamide Chemical compound NC(=O)CSC1=CC=CC=C1 KBRJQEVSKVOLNR-UHFFFAOYSA-N 0.000 description 1
- NBTBMGFDYMZMTC-UHFFFAOYSA-N 2-propan-2-ylsulfanylacetamide Chemical compound CC(C)SCC(N)=O NBTBMGFDYMZMTC-UHFFFAOYSA-N 0.000 description 1
- DZQILWIIDUJZBN-UHFFFAOYSA-N 2-propylsulfanylacetamide Chemical compound CCCSCC(N)=O DZQILWIIDUJZBN-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- COXVTLYNGOIATD-HVMBLDELSA-N CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O Chemical class CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O COXVTLYNGOIATD-HVMBLDELSA-N 0.000 description 1
- 101000783577 Dendroaspis angusticeps Thrombostatin Proteins 0.000 description 1
- 101000783578 Dendroaspis jamesoni kaimosae Dendroaspin Proteins 0.000 description 1
- ITIONVBQFUNVJV-UHFFFAOYSA-N Etomidoline Chemical compound C12=CC=CC=C2C(=O)N(CC)C1NC(C=C1)=CC=C1OCCN1CCCCC1 ITIONVBQFUNVJV-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- CRZQGDNQQAALAY-UHFFFAOYSA-N Me ester-Phenylacetic acid Natural products COC(=O)CC1=CC=CC=C1 CRZQGDNQQAALAY-UHFFFAOYSA-N 0.000 description 1
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- QZNJPJDUBTYMRS-UHFFFAOYSA-M amfenac sodium hydrate Chemical compound O.[Na+].NC1=C(CC([O-])=O)C=CC=C1C(=O)C1=CC=CC=C1 QZNJPJDUBTYMRS-UHFFFAOYSA-M 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000001458 anti-acid effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 229940127218 antiplatelet drug Drugs 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000003637 basic solution Substances 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
- 239000000872 buffer Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000007963 capsule composition Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 description 1
- 229960004926 chlorobutanol Drugs 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 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
- 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 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- XQGLNUVQVKZRRR-UHFFFAOYSA-N ethyl 2-(2-amino-3-benzoylphenyl)acetate Chemical compound CCOC(=O)CC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1N XQGLNUVQVKZRRR-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 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
- 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
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000014380 magnesium carbonate Nutrition 0.000 description 1
- UNDMMNILNUQQOV-UHFFFAOYSA-N methyl 3-oxo-2,3-diphenylpropanoate Chemical compound C=1C=CC=CC=1C(C(=O)OC)C(=O)C1=CC=CC=C1 UNDMMNILNUQQOV-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- LOYRIIRPKHCMAD-UHFFFAOYSA-N n-acetyl-n-phenylbenzamide Chemical class C=1C=CC=CC=1N(C(=O)C)C(=O)C1=CC=CC=C1 LOYRIIRPKHCMAD-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- QEFAQIPZVLVERP-UHFFFAOYSA-N nepafenac Chemical compound NC(=O)CC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1N QEFAQIPZVLVERP-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- FFXIGVUMVPUWDK-UHFFFAOYSA-N pentanethioamide Chemical compound CCCCC(N)=S FFXIGVUMVPUWDK-UHFFFAOYSA-N 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000000106 platelet aggregation inhibitor Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- SMOPCACDYYHOPI-UHFFFAOYSA-M potassium;2-(2-amino-3-benzoylphenyl)acetate;hydrate Chemical compound O.[K+].NC1=C(CC([O-])=O)C=CC=C1C(=O)C1=CC=CC=C1 SMOPCACDYYHOPI-UHFFFAOYSA-M 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- WPZSAUFQHYFIPG-UHFFFAOYSA-N propanethioamide Chemical compound CCC(N)=S WPZSAUFQHYFIPG-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 229940006198 sodium phenylacetate Drugs 0.000 description 1
- SWAULJUBWSQJIE-UHFFFAOYSA-M sodium;2-(2-amino-3-benzoyl-5-chlorophenyl)acetate Chemical compound [Na+].NC1=C(CC([O-])=O)C=C(Cl)C=C1C(=O)C1=CC=CC=C1 SWAULJUBWSQJIE-UHFFFAOYSA-M 0.000 description 1
- HHMNMLHPCDSULA-UHFFFAOYSA-M sodium;2-(2-amino-3-benzoylphenyl)acetate;dihydrate Chemical compound O.O.[Na+].NC1=C(CC([O-])=O)C=CC=C1C(=O)C1=CC=CC=C1 HHMNMLHPCDSULA-UHFFFAOYSA-M 0.000 description 1
- FVBKCOXGVZPEDP-UHFFFAOYSA-M sodium;2-[2-amino-3-(4-chlorobenzoyl)phenyl]acetate Chemical compound [Na+].NC1=C(CC([O-])=O)C=CC=C1C(=O)C1=CC=C(Cl)C=C1 FVBKCOXGVZPEDP-UHFFFAOYSA-M 0.000 description 1
- BJALDACDVYCCOM-UHFFFAOYSA-M sodium;2-[2-amino-3-(4-chlorobenzoyl)phenyl]acetate;hydrate Chemical compound O.[Na+].NC1=C(CC([O-])=O)C=CC=C1C(=O)C1=CC=C(Cl)C=C1 BJALDACDVYCCOM-UHFFFAOYSA-M 0.000 description 1
- QEXUQZXGARIKTK-UHFFFAOYSA-M sodium;2-[2-amino-3-[hydroxy(phenyl)methyl]phenyl]acetate Chemical compound [Na+].NC1=C(CC([O-])=O)C=CC=C1C(O)C1=CC=CC=C1 QEXUQZXGARIKTK-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- 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)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pain & Pain Management (AREA)
- Pharmacology & Pharmacy (AREA)
- Rheumatology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12254480A | 1980-02-19 | 1980-02-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56131552A JPS56131552A (en) | 1981-10-15 |
| JPH0153266B2 true JPH0153266B2 (sv) | 1989-11-13 |
Family
ID=22403319
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2363881A Granted JPS56131552A (en) | 1980-02-19 | 1981-02-19 | Novel phenylacetic acid compound and antiinflammatory thereof |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS56131552A (sv) |
| AU (1) | AU538240B2 (sv) |
| BE (1) | BE887566A (sv) |
| CA (1) | CA1156655A (sv) |
| CH (1) | CH648283A5 (sv) |
| DE (1) | DE3105285A1 (sv) |
| FR (1) | FR2476071A1 (sv) |
| GB (1) | GB2071086B (sv) |
| IL (1) | IL61945A (sv) |
| IT (1) | IT1146744B (sv) |
| NL (1) | NL8100808A (sv) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA805476B (en) * | 1979-09-26 | 1981-11-25 | Robins Co Inc A H | 2-amino-3-benzoyl-phenylacetamides and cyclic homologues |
| IL64724A0 (en) * | 1981-02-17 | 1982-03-31 | Robins Co Inc A H | 2-amino-3-(halobenzoyl)-methylphenylacetic acids and esters and salts thereof and pharmaceutical compositions containing them |
| US5475034A (en) * | 1994-06-06 | 1995-12-12 | Alcon Laboratories, Inc. | Topically administrable compositions containing 3-benzoylphenylacetic acid derivatives for treatment of ophthalmic inflammatory disorders |
| AR030345A1 (es) * | 2000-08-14 | 2003-08-20 | Alcon Inc | Metodo de tratamiento de desordenes relacionados con angiogenesis |
| AR030346A1 (es) * | 2000-08-14 | 2003-08-20 | Alcon Inc | Metodo de tratamiento de desordenes neurodegenerativos de la retina y cabeza de nervio optico |
| WO2002078681A2 (en) | 2001-04-02 | 2002-10-10 | Alcon, Inc. | Method of treating ocular inflammatory and angiogenesis-related disorders using an amide derivative of flubiprofen or ketorolac |
| TWI358290B (en) | 2004-12-02 | 2012-02-21 | Alcon Inc | Topical nepafenac formulations |
| CA2755314A1 (en) * | 2009-03-12 | 2010-09-16 | Medichem, S.A. | New crystals of a benzoylbenzeneacetamide derivative |
| EP2389354A1 (en) * | 2009-04-06 | 2011-11-30 | Medichem, S.A. | 2-{2-amino-3-ýhydroxy(phenyl)methyl¨phenyl} acetamide |
| CN106631881B (zh) * | 2016-09-08 | 2018-09-21 | 南京工业大学 | 2-（3-苄基-2-（二甲基氨基）苯基）乙酰胺及合成方法和用途 |
| CN112794809B (zh) * | 2019-11-14 | 2023-12-29 | 南京济群医药科技股份有限公司 | 一种高纯度奈帕芬胺中间体的制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE400966B (sv) * | 1975-08-13 | 1978-04-17 | Robins Co Inc A H | Forfarande for framstellning av 2-amino-3-(eller 5-)bensoyl-fenylettiksyror |
| FR2366015A1 (fr) * | 1975-11-05 | 1978-04-28 | Robins Co Inc A H | Nouveaux acides amino-2 benzoyl-3 (5 et 6) phenylacetiques et leurs esters et sels de metaux alcalins, utiles notamment comme anti-inflammatoires, et leur procede de preparation |
| ZA805476B (en) * | 1979-09-26 | 1981-11-25 | Robins Co Inc A H | 2-amino-3-benzoyl-phenylacetamides and cyclic homologues |
-
1981
- 1981-01-20 IL IL61945A patent/IL61945A/xx unknown
- 1981-02-09 IT IT67177/81A patent/IT1146744B/it active
- 1981-02-13 DE DE19813105285 patent/DE3105285A1/de not_active Withdrawn
- 1981-02-16 AU AU67330/81A patent/AU538240B2/en not_active Ceased
- 1981-02-18 GB GB8105091A patent/GB2071086B/en not_active Expired
- 1981-02-18 BE BE0/203830A patent/BE887566A/fr not_active IP Right Cessation
- 1981-02-18 NL NL8100808A patent/NL8100808A/nl not_active Application Discontinuation
- 1981-02-18 CH CH1076/81A patent/CH648283A5/fr not_active IP Right Cessation
- 1981-02-18 FR FR8103188A patent/FR2476071A1/fr active Granted
- 1981-02-18 CA CA000371185A patent/CA1156655A/en not_active Expired
- 1981-02-19 JP JP2363881A patent/JPS56131552A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| IL61945A0 (en) | 1981-02-27 |
| FR2476071B1 (sv) | 1984-05-11 |
| GB2071086B (en) | 1984-02-08 |
| IT8167177A0 (it) | 1981-02-09 |
| JPS56131552A (en) | 1981-10-15 |
| BE887566A (fr) | 1981-06-15 |
| AU6733081A (en) | 1981-08-27 |
| AU538240B2 (en) | 1984-08-02 |
| NL8100808A (nl) | 1981-09-16 |
| DE3105285A1 (de) | 1982-01-21 |
| GB2071086A (en) | 1981-09-16 |
| CA1156655A (en) | 1983-11-08 |
| IL61945A (en) | 1984-09-30 |
| IT1146744B (it) | 1986-11-19 |
| FR2476071A1 (fr) | 1981-08-21 |
| CH648283A5 (fr) | 1985-03-15 |
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