CS227012B2 - Method of preparing 2-amino-3-benzoyl-phenylacetamide - Google Patents
Method of preparing 2-amino-3-benzoyl-phenylacetamide Download PDFInfo
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- CS227012B2 CS227012B2 CS806196A CS619680A CS227012B2 CS 227012 B2 CS227012 B2 CS 227012B2 CS 806196 A CS806196 A CS 806196A CS 619680 A CS619680 A CS 619680A CS 227012 B2 CS227012 B2 CS 227012B2
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- amino
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- QEFAQIPZVLVERP-UHFFFAOYSA-N nepafenac Chemical compound NC(=O)CC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1N QEFAQIPZVLVERP-UHFFFAOYSA-N 0.000 title claims abstract description 5
- 238000000034 method Methods 0.000 title claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 40
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 36
- 150000001875 compounds Chemical class 0.000 claims abstract description 32
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 78
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 36
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 33
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 18
- 239000007868 Raney catalyst Substances 0.000 claims description 13
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- CJXBHFANXQMZBF-UHFFFAOYSA-N 2-phenylethanethioamide Chemical compound NC(=S)CC1=CC=CC=C1 CJXBHFANXQMZBF-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims 1
- GUGRBFQNXVKOGR-UHFFFAOYSA-N butyl hypochlorite Chemical group CCCCOCl GUGRBFQNXVKOGR-UHFFFAOYSA-N 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 7
- 230000000202 analgesic effect Effects 0.000 abstract description 3
- 230000001754 anti-pyretic effect Effects 0.000 abstract description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 3
- 230000000144 pharmacologic effect Effects 0.000 abstract description 3
- 239000002221 antipyretic Substances 0.000 abstract description 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 3
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 239000008280 blood Substances 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 abstract 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 59
- 239000000203 mixture Substances 0.000 description 40
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
- 238000004458 analytical method Methods 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 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
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 14
- -1 Methylthioacetyl Chemical group 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 9
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
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- 230000035602 clotting Effects 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
- 239000002775 capsule Substances 0.000 description 6
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 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
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- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical class NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 206010061218 Inflammation Diseases 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- 230000004054 inflammatory process Effects 0.000 description 4
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 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 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 206010053155 Epigastric discomfort Diseases 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 3
- 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 2
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 2
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- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- MDIAKIHKBBNYHF-UHFFFAOYSA-N Ethyl 2-(methylthio)acetate Chemical compound CCOC(=O)CSC MDIAKIHKBBNYHF-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
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- 150000001412 amines Chemical class 0.000 description 2
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- FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 2
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- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- DKLPITJCVWPEAJ-UHFFFAOYSA-N 2-(2-amino-3-benzoyl-5-chlorophenyl)-2-(4-chlorophenyl)sulfanylacetamide Chemical compound C=1C(Cl)=CC(C(=O)C=2C=CC=CC=2)=C(N)C=1C(C(=O)N)SC1=CC=C(Cl)C=C1 DKLPITJCVWPEAJ-UHFFFAOYSA-N 0.000 description 1
- KGMINWKBJFPMMI-UHFFFAOYSA-N 2-(2-amino-3-benzoyl-5-chlorophenyl)-2-phenylsulfanylacetamide Chemical compound C=1C(Cl)=CC(C(=O)C=2C=CC=CC=2)=C(N)C=1C(C(=O)N)SC1=CC=CC=C1 KGMINWKBJFPMMI-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
- CBDVPOKBVAEIMF-UHFFFAOYSA-N 2-(2-amino-3-benzoylphenyl)-n,n-dimethylacetamide Chemical compound CN(C)C(=O)CC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1N CBDVPOKBVAEIMF-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
- QNWIYGLXIXTHKG-UHFFFAOYSA-N 2-[2-amino-3-(4-chlorobenzoyl)-5-fluorophenyl]acetamide Chemical compound NC1=C(C=C(C=C1C(C1=CC=C(C=C1)Cl)=O)F)CC(=O)N QNWIYGLXIXTHKG-UHFFFAOYSA-N 0.000 description 1
- GBBWTEGVCMKKAK-UHFFFAOYSA-N 2-[2-amino-3-(4-chlorobenzoyl)phenyl]-2-phenylsulfanylacetamide Chemical compound C=1C=CC(C(=O)C=2C=CC(Cl)=CC=2)=C(N)C=1C(C(=O)N)SC1=CC=CC=C1 GBBWTEGVCMKKAK-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
- GRRCDRIBJQKMEW-UHFFFAOYSA-N 2-ethyl-2-phenylbutanamide Chemical compound CCC(CC)(C(N)=O)C1=CC=CC=C1 GRRCDRIBJQKMEW-UHFFFAOYSA-N 0.000 description 1
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- KBRJQEVSKVOLNR-UHFFFAOYSA-N 2-phenylsulfanylacetamide Chemical compound NC(=O)CSC1=CC=CC=C1 KBRJQEVSKVOLNR-UHFFFAOYSA-N 0.000 description 1
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- NTMLLKRWCFUOAP-UHFFFAOYSA-N 3-oxo-2,3-diphenylpropanamide Chemical class C=1C=CC=CC=1C(C(=O)N)C(=O)C1=CC=CC=C1 NTMLLKRWCFUOAP-UHFFFAOYSA-N 0.000 description 1
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- 238000002347 injection Methods 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 238000001990 intravenous administration Methods 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
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Chemical class 0.000 description 1
- 239000002184 metal Chemical class 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- LYDAHNXGYJRKLL-UHFFFAOYSA-N n,n-dimethyl-2-methylsulfanylacetamide Chemical compound CSCC(=O)N(C)C LYDAHNXGYJRKLL-UHFFFAOYSA-N 0.000 description 1
- OEXMNSOPAKOPEF-UHFFFAOYSA-N n-[4-[(4-acetamidophenyl)methyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1CC1=CC=C(NC(C)=O)C=C1 OEXMNSOPAKOPEF-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 210000004623 platelet-rich plasma Anatomy 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 238000003672 processing method Methods 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
- 150000003839 salts Chemical class 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 230000036269 ulceration Effects 0.000 description 1
- 239000008215 water for injection 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Rheumatology (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 |
|---|---|---|---|
| US7886079A | 1979-09-26 | 1979-09-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS227012B2 true CS227012B2 (en) | 1984-04-16 |
Family
ID=22146633
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS806196A CS227012B2 (en) | 1979-09-26 | 1980-09-11 | Method of preparing 2-amino-3-benzoyl-phenylacetamide |
Country Status (36)
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL61945A (en) * | 1980-02-19 | 1984-09-30 | Robins Co Inc A H | 2-amino-3-(hydroxy(phenyl)methyl)phenylacetic acids,esters and amides and pharmaceutical compositions containing them |
| US6066671A (en) | 1997-12-19 | 2000-05-23 | Alcon Laboratories, Inc. | Treatment of GLC1A glaucoma with 3-benzoyl-phenylacetic acids, esters, or amides |
| US6646001B2 (en) | 1997-12-19 | 2003-11-11 | Alcon Manufacturing, Ltd. | Use of non-steroidal anti-inflammatory agents in combination with prostaglandin FP receptor agonists to treat glaucoma and ocular hypertension |
| GB9727523D0 (en) | 1997-12-31 | 1998-02-25 | Pharmacia & Upjohn Spa | Alpha-aminoamide derivatives useful as analgesic agents |
| AR030345A1 (es) * | 2000-08-14 | 2003-08-20 | Alcon Inc | Metodo de tratamiento de desordenes relacionados con angiogenesis |
| AU2002333374B2 (en) | 2001-09-03 | 2007-03-22 | Newron Pharmaceuticals S.P.A. | Pharmaceutical composition comprising gabapentin or an analogue thereof and an (alpha)- aminoamide and its analgesic use |
| EP1438956A1 (en) | 2003-01-16 | 2004-07-21 | Newron Pharmaceuticals S.p.A. | Alpha-aminoamide derivatives useful as antimigraine agents |
| CZ2009367A3 (cs) * | 2009-06-08 | 2010-06-16 | Farmak, A.S. | Postup prípravy 2-amino-3-benzoylfenylacetamidu (nepafenacu) s minimem vedlejších produktu |
| 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 |
|---|---|---|---|---|
| GB1226344A (en, 2012) * | 1967-07-31 | 1971-03-24 | ||
| SE400966B (sv) * | 1975-08-13 | 1978-04-17 | Robins Co Inc A H | Forfarande for framstellning av 2-amino-3-(eller 5-)bensoyl-fenylettiksyror |
| IL61945A (en) * | 1980-02-19 | 1984-09-30 | Robins Co Inc A H | 2-amino-3-(hydroxy(phenyl)methyl)phenylacetic acids,esters and amides and pharmaceutical compositions containing them |
-
1980
- 1980-09-04 ZA ZA00805476A patent/ZA805476B/xx unknown
- 1980-09-08 IL IL60999A patent/IL60999A/xx unknown
- 1980-09-08 AU AU62116/80A patent/AU532359B2/en not_active Ceased
- 1980-09-11 CS CS806196A patent/CS227012B2/cs unknown
- 1980-09-17 IE IE1946/80A patent/IE50268B1/en unknown
- 1980-09-20 EG EG80573A patent/EG15020A/xx active
- 1980-09-22 GR GR62936A patent/GR70049B/el unknown
- 1980-09-22 BR BR8006042A patent/BR8006042A/pt unknown
- 1980-09-22 DE DE19803035688 patent/DE3035688A1/de active Granted
- 1980-09-23 AT AT0474580A patent/AT374170B/de not_active IP Right Cessation
- 1980-09-23 PH PH24613A patent/PH22628A/en unknown
- 1980-09-24 LU LU82797A patent/LU82797A1/fr unknown
- 1980-09-24 SE SE8006668A patent/SE448626B/sv not_active IP Right Cessation
- 1980-09-24 FI FI803002A patent/FI72967C/fi not_active IP Right Cessation
- 1980-09-25 NL NL8005346A patent/NL8005346A/nl not_active Application Discontinuation
- 1980-09-25 ES ES495329A patent/ES8200329A1/es not_active Expired
- 1980-09-25 YU YU2450/80A patent/YU41734B/xx unknown
- 1980-09-25 KR KR1019800003740A patent/KR840000763B1/ko not_active Expired
- 1980-09-25 MX MX809050U patent/MX7159E/es unknown
- 1980-09-25 HU HU802347A patent/HU183215B/hu not_active IP Right Cessation
- 1980-09-25 CA CA361,068A patent/CA1128512A/en not_active Expired
- 1980-09-25 CH CH719180A patent/CH646138A5/fr not_active IP Right Cessation
- 1980-09-25 FR FR8020596A patent/FR2465710A1/fr active Granted
- 1980-09-25 PT PT71839A patent/PT71839B/pt unknown
- 1980-09-25 NO NO802834A patent/NO152128C/no unknown
- 1980-09-25 GB GB8030955A patent/GB2059963B/en not_active Expired
- 1980-09-25 PL PL1980226919A patent/PL128998B1/pl unknown
- 1980-09-25 DK DK405780A patent/DK154136C/da not_active IP Right Cessation
- 1980-09-25 BE BE0/202226A patent/BE885393A/fr not_active IP Right Cessation
- 1980-09-26 JP JP13415280A patent/JPS5657751A/ja active Granted
- 1980-09-26 IT IT24948/80A patent/IT1133823B/it active
- 1980-09-26 IN IN1092/CAL/80A patent/IN151313B/en unknown
- 1980-09-26 NZ NZ195061A patent/NZ195061A/en unknown
-
1981
- 1981-06-12 ES ES503019A patent/ES503019A0/es active Granted
-
1982
- 1982-12-30 IN IN1509/CAL/82A patent/IN156255B/en unknown
- 1982-12-30 IN IN1508/CAL/82A patent/IN156254B/en unknown
-
1983
- 1983-03-28 YU YU730/83A patent/YU43305B/xx unknown
- 1983-03-28 YU YU731/83A patent/YU43306B/xx unknown
- 1983-07-19 SG SG42983A patent/SG42983G/en unknown
- 1983-07-21 KE KE3307A patent/KE3307A/xx unknown
- 1983-11-24 HK HK593/83A patent/HK59383A/xx unknown
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