CA1050556A - Aminopyrrole derivatives - Google Patents
Aminopyrrole derivativesInfo
- Publication number
- CA1050556A CA1050556A CA207,472A CA207472A CA1050556A CA 1050556 A CA1050556 A CA 1050556A CA 207472 A CA207472 A CA 207472A CA 1050556 A CA1050556 A CA 1050556A
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- hydrogen
- amino
- acetyl
- process according
- 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
- QLSWIGRIBOSFMV-UHFFFAOYSA-N 1h-pyrrol-2-amine Chemical class NC1=CC=CN1 QLSWIGRIBOSFMV-UHFFFAOYSA-N 0.000 title abstract description 13
- -1 (C2-4)aliphatic acyl Chemical group 0.000 claims abstract description 139
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 74
- 239000001257 hydrogen Substances 0.000 claims abstract description 74
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 33
- 239000002253 acid Substances 0.000 claims abstract description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 28
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 24
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 22
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 22
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 22
- 150000003839 salts Chemical class 0.000 claims abstract description 22
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 16
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 15
- 150000007513 acids Chemical class 0.000 claims abstract description 12
- 125000001118 alkylidene group Chemical group 0.000 claims abstract description 10
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims abstract description 10
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 6
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 23
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 18
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims description 234
- 238000000034 method Methods 0.000 claims description 89
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 38
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 36
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 claims description 32
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
- 125000001424 substituent group Chemical group 0.000 claims description 28
- 239000000126 substance Substances 0.000 claims description 27
- JTIHSSVKTWPPHI-UHFFFAOYSA-N 2-amino-2-phenylacetonitrile Chemical compound N#CC(N)C1=CC=CC=C1 JTIHSSVKTWPPHI-UHFFFAOYSA-N 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 230000000875 corresponding effect Effects 0.000 claims description 19
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 16
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 15
- 125000001153 fluoro group Chemical group F* 0.000 claims description 15
- 239000011541 reaction mixture Substances 0.000 claims description 15
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 9
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 8
- 125000001246 bromo group Chemical group Br* 0.000 claims description 8
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 8
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 8
- 229910021529 ammonia Inorganic materials 0.000 claims description 7
- 239000002585 base Substances 0.000 claims description 7
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 claims description 7
- 229940093858 ethyl acetoacetate Drugs 0.000 claims description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
- 230000002152 alkylating effect Effects 0.000 claims description 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 claims description 6
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 5
- 230000007062 hydrolysis Effects 0.000 claims description 5
- 238000006460 hydrolysis reaction Methods 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 238000010992 reflux Methods 0.000 claims description 5
- CVBUKMMMRLOKQR-UHFFFAOYSA-N 1-phenylbutane-1,3-dione Chemical compound CC(=O)CC(=O)C1=CC=CC=C1 CVBUKMMMRLOKQR-UHFFFAOYSA-N 0.000 claims description 4
- JBPGQESINKVYLD-UHFFFAOYSA-N 2-amino-2-(4-methylphenyl)acetonitrile Chemical compound CC1=CC=C(C(N)C#N)C=C1 JBPGQESINKVYLD-UHFFFAOYSA-N 0.000 claims description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- VHILMKFSCRWWIJ-UHFFFAOYSA-N dimethyl acetylenedicarboxylate Chemical group COC(=O)C#CC(=O)OC VHILMKFSCRWWIJ-UHFFFAOYSA-N 0.000 claims description 4
- QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical compound S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- JAUKOLRHHAJVST-UHFFFAOYSA-N 2-amino-2-(4-chlorophenyl)acetonitrile Chemical compound N#CC(N)C1=CC=C(Cl)C=C1 JAUKOLRHHAJVST-UHFFFAOYSA-N 0.000 claims description 3
- SKNIWUSHIRPONJ-UHFFFAOYSA-N 2-amino-2-(4-methoxyphenyl)acetonitrile Chemical compound COC1=CC=C(C(N)C#N)C=C1 SKNIWUSHIRPONJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- DFNYGALUNNFWKJ-UHFFFAOYSA-N aminoacetonitrile Chemical compound NCC#N DFNYGALUNNFWKJ-UHFFFAOYSA-N 0.000 claims description 3
- CPEKAXYCDKETEN-UHFFFAOYSA-N benzoyl isothiocyanate Chemical compound S=C=NC(=O)C1=CC=CC=C1 CPEKAXYCDKETEN-UHFFFAOYSA-N 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 229910052736 halogen Chemical group 0.000 claims description 3
- 150000004679 hydroxides Chemical class 0.000 claims description 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 3
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 claims description 3
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- HAEXHZOJAUQXNI-UHFFFAOYSA-N 2-amino-2-(4-fluorophenyl)acetonitrile Chemical compound N#CC(N)C1=CC=C(F)C=C1 HAEXHZOJAUQXNI-UHFFFAOYSA-N 0.000 claims description 2
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 claims description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 150000001299 aldehydes Chemical class 0.000 claims description 2
- 150000004703 alkoxides Chemical class 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 2
- 150000004678 hydrides Chemical class 0.000 claims description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229940117953 phenylisothiocyanate Drugs 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims 7
- LNHXCTFGBVFGMW-UHFFFAOYSA-N 1-(4-amino-2-methyl-5-phenyl-1h-pyrrol-3-yl)ethanone Chemical compound CC(=O)C1=C(C)NC(C=2C=CC=CC=2)=C1N LNHXCTFGBVFGMW-UHFFFAOYSA-N 0.000 claims 6
- ACCXJQPXBSUOFK-UHFFFAOYSA-N 1-[4-(benzylideneamino)-2-methyl-5-phenyl-1h-pyrrol-3-yl]ethanone Chemical compound CC(=O)C1=C(C)NC(C=2C=CC=CC=2)=C1N=CC1=CC=CC=C1 ACCXJQPXBSUOFK-UHFFFAOYSA-N 0.000 claims 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 3
- KYGFWQIOYBDYBN-UHFFFAOYSA-N (4-amino-2-methyl-5-phenyl-1h-pyrrol-3-yl)-phenylmethanone Chemical compound CC=1NC(C=2C=CC=CC=2)=C(N)C=1C(=O)C1=CC=CC=C1 KYGFWQIOYBDYBN-UHFFFAOYSA-N 0.000 claims 2
- UMSWVMUFXHQAPJ-UHFFFAOYSA-N 1-(4-amino-2-methyl-5-phenyl-1h-pyrrol-3-yl)-2-methylpropan-1-one Chemical compound CC(C)C(=O)C1=C(C)NC(C=2C=CC=CC=2)=C1N UMSWVMUFXHQAPJ-UHFFFAOYSA-N 0.000 claims 2
- BYUYNAIABNAPDI-UHFFFAOYSA-N 1-[1-[(4-chlorophenyl)methyl]-4-(dimethylamino)-2-methyl-5-phenylpyrrol-3-yl]ethanone Chemical compound C=1C=CC=CC=1C1=C(N(C)C)C(C(C)=O)=C(C)N1CC1=CC=C(Cl)C=C1 BYUYNAIABNAPDI-UHFFFAOYSA-N 0.000 claims 2
- KQITZZMVHAWHEA-UHFFFAOYSA-N 1-[4-[(4-chlorophenyl)methylideneamino]-2-methyl-5-phenyl-1h-pyrrol-3-yl]ethanone Chemical compound CC(=O)C1=C(C)NC(C=2C=CC=CC=2)=C1N=CC1=CC=C(Cl)C=C1 KQITZZMVHAWHEA-UHFFFAOYSA-N 0.000 claims 2
- PKZOONNWUOLMES-UHFFFAOYSA-N 1-[4-amino-2-methyl-5-(4-methylphenyl)-1h-pyrrol-3-yl]ethanone Chemical compound CC(=O)C1=C(C)NC(C=2C=CC(C)=CC=2)=C1N PKZOONNWUOLMES-UHFFFAOYSA-N 0.000 claims 2
- OOIDVVFBVRBJSS-UHFFFAOYSA-N 1-[4-amino-5-(4-chlorophenyl)-2-methyl-1h-pyrrol-3-yl]ethanone Chemical compound CC(=O)C1=C(C)NC(C=2C=CC(Cl)=CC=2)=C1N OOIDVVFBVRBJSS-UHFFFAOYSA-N 0.000 claims 2
- SWLGHYJGPQLDBS-UHFFFAOYSA-N 1-[4-amino-5-(4-fluorophenyl)-2-methyl-1h-pyrrol-3-yl]ethanone Chemical compound CC(=O)C1=C(C)NC(C=2C=CC(F)=CC=2)=C1N SWLGHYJGPQLDBS-UHFFFAOYSA-N 0.000 claims 2
- XUGRXPRIBPIHJJ-UHFFFAOYSA-N 1-[4-amino-5-(4-methoxyphenyl)-2-methyl-1h-pyrrol-3-yl]ethanone Chemical compound C1=CC(OC)=CC=C1C1=C(N)C(C(C)=O)=C(C)N1 XUGRXPRIBPIHJJ-UHFFFAOYSA-N 0.000 claims 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims 2
- KQPMCNYVPIBLHE-UHFFFAOYSA-N methyl 4-amino-2-carbamoyl-5-phenyl-1h-pyrrole-3-carboxylate Chemical compound N1C(C(N)=O)=C(C(=O)OC)C(N)=C1C1=CC=CC=C1 KQPMCNYVPIBLHE-UHFFFAOYSA-N 0.000 claims 2
- 230000001035 methylating effect Effects 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- OECCKFYMDPOMDS-UHFFFAOYSA-N 1-(4-amino-1,2-dimethyl-5-phenylpyrrol-3-yl)ethanone Chemical compound CN1C(C)=C(C(=O)C)C(N)=C1C1=CC=CC=C1 OECCKFYMDPOMDS-UHFFFAOYSA-N 0.000 claims 1
- MLFFAHVRUAJXRJ-UHFFFAOYSA-N 1-[4-(benzylideneamino)-1,2-dimethyl-5-phenylpyrrol-3-yl]ethanone Chemical compound CC(=O)C1=C(C)N(C)C(C=2C=CC=CC=2)=C1N=CC1=CC=CC=C1 MLFFAHVRUAJXRJ-UHFFFAOYSA-N 0.000 claims 1
- MNFJJFDADFHHQQ-UHFFFAOYSA-N 1-[4-(dimethylamino)-2-methyl-5-phenyl-1h-pyrrol-3-yl]ethanone Chemical compound N1C(C)=C(C(C)=O)C(N(C)C)=C1C1=CC=CC=C1 MNFJJFDADFHHQQ-UHFFFAOYSA-N 0.000 claims 1
- 125000003541 2-chlorobenzoyl group Chemical group ClC1=C(C(=O)*)C=CC=C1 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- KHZGUWAFFHXZLC-UHFFFAOYSA-N 5-methylhexane-2,4-dione Chemical compound CC(C)C(=O)CC(C)=O KHZGUWAFFHXZLC-UHFFFAOYSA-N 0.000 claims 1
- 230000000397 acetylating effect Effects 0.000 claims 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims 1
- VGMBZQHZLGPKMU-UHFFFAOYSA-N dimethyl 4-amino-5-phenyl-1h-pyrrole-2,3-dicarboxylate Chemical compound COC(=O)C1=C(C(=O)OC)NC(C=2C=CC=CC=2)=C1N VGMBZQHZLGPKMU-UHFFFAOYSA-N 0.000 claims 1
- PZKPUKNJNZNOMZ-UHFFFAOYSA-N ethyl 4-acetamido-2-methyl-1H-pyrrole-3-carboxylate Chemical compound C(C)(=O)NC1=CNC(=C1C(=O)OCC)C PZKPUKNJNZNOMZ-UHFFFAOYSA-N 0.000 claims 1
- PJVUAXFCCTZDDR-UHFFFAOYSA-N ethyl 4-amino-2-methyl-1h-pyrrole-3-carboxylate Chemical compound CCOC(=O)C1=C(C)NC=C1N PJVUAXFCCTZDDR-UHFFFAOYSA-N 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 155
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 105
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 104
- 239000000460 chlorine Substances 0.000 description 46
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
- 239000000543 intermediate Substances 0.000 description 27
- 239000000243 solution Substances 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 23
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000000203 mixture Substances 0.000 description 18
- 239000000047 product Substances 0.000 description 15
- 238000001914 filtration Methods 0.000 description 11
- 239000002244 precipitate Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 8
- 229940093499 ethyl acetate Drugs 0.000 description 8
- 235000019439 ethyl acetate Nutrition 0.000 description 8
- 241000700159 Rattus Species 0.000 description 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 7
- 239000012458 free base Substances 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 206010030113 Oedema Diseases 0.000 description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- 230000003110 anti-inflammatory effect Effects 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 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 4
- 241000699670 Mus sp. Species 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000007363 ring formation reaction Methods 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- DQQIUVCNBOJDGF-UHFFFAOYSA-N 2-aminobutanenitrile Chemical compound CCC(N)C#N DQQIUVCNBOJDGF-UHFFFAOYSA-N 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
-
- 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]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- 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
- C07D209/40—Nitrogen atoms, not forming part of a nitro radical, e.g. isatin semicarbazone
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Rheumatology (AREA)
- Pharmacology & Pharmacy (AREA)
- Pain & Pain Management (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3979073A GB1427945A (en) | 1973-08-22 | 1973-08-22 | Aminopyrrole derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1050556A true CA1050556A (en) | 1979-03-13 |
Family
ID=10411528
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA207,472A Expired CA1050556A (en) | 1973-08-22 | 1974-08-21 | Aminopyrrole derivatives |
Country Status (27)
| Country | Link |
|---|---|
| JP (1) | JPS5328914B2 (en, 2012) |
| AR (3) | AR210246A1 (en, 2012) |
| AT (1) | AT336600B (en, 2012) |
| BE (1) | BE819088A (en, 2012) |
| CA (1) | CA1050556A (en, 2012) |
| CH (1) | CH605741A5 (en, 2012) |
| CS (1) | CS188201B2 (en, 2012) |
| DD (1) | DD113756A5 (en, 2012) |
| DE (4) | DE2462966C2 (en, 2012) |
| DK (1) | DK156391C (en, 2012) |
| ES (3) | ES429446A1 (en, 2012) |
| FI (1) | FI61879C (en, 2012) |
| FR (1) | FR2241308B1 (en, 2012) |
| GB (1) | GB1427945A (en, 2012) |
| HU (1) | HU169728B (en, 2012) |
| IE (1) | IE40290B1 (en, 2012) |
| IL (1) | IL45368A (en, 2012) |
| IN (1) | IN140329B (en, 2012) |
| LU (1) | LU70764A1 (en, 2012) |
| NL (1) | NL7411092A (en, 2012) |
| NO (1) | NO143845C (en, 2012) |
| PL (2) | PL95235B1 (en, 2012) |
| RO (3) | RO70534A (en, 2012) |
| SE (1) | SE394429B (en, 2012) |
| SU (1) | SU843738A3 (en, 2012) |
| YU (1) | YU36926B (en, 2012) |
| ZA (1) | ZA744754B (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1492663A (en) * | 1975-02-20 | 1977-11-23 | Lepetit Spa | 4-amino-3-pyrrole carboxamides |
| GB1548398A (en) * | 1975-06-05 | 1979-07-11 | Lilly Industries Ltd | Acylamino pyrroles furans and thiophenes |
| DE3212591A1 (de) * | 1982-04-03 | 1983-10-13 | Gödecke AG, 1000 Berlin | 2-pyrrolin-3-carbonitril-derivate, verfahren zu deren herstellung und diese enthaltende arzneimittel |
| JPH0216740U (en, 2012) * | 1988-07-21 | 1990-02-02 | ||
| DE59009489D1 (de) * | 1989-03-28 | 1995-09-14 | Ciba Geigy Ag | Substituierte Aminopyrrole als Stabilisatoren chlorhaltige Polymerisate. |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1148909A (en) * | 1965-04-19 | 1969-04-16 | Sumitomo Chemical Co | Process for production of novel phenylhydrazone and phenylhydrazine derivatives |
| GB1187903A (en) * | 1967-09-29 | 1970-04-15 | Sumitomo Chemical Co | Glucuronides of 3-Indolylaliphatic Acid Derivatives and Processes for Producing them |
-
1973
- 1973-08-22 GB GB3979073A patent/GB1427945A/en not_active Expired
-
1974
- 1974-07-27 ZA ZA00744754A patent/ZA744754B/xx unknown
- 1974-07-29 IL IL45368A patent/IL45368A/en unknown
- 1974-08-01 YU YU2141/74A patent/YU36926B/xx unknown
- 1974-08-08 NO NO742862A patent/NO143845C/no unknown
- 1974-08-08 IE IE1672/74A patent/IE40290B1/en unknown
- 1974-08-16 DE DE2462966A patent/DE2462966C2/de not_active Expired
- 1974-08-16 DE DE2462967A patent/DE2462967C2/de not_active Expired
- 1974-08-16 DE DE2439284A patent/DE2439284C2/de not_active Expired
- 1974-08-16 DE DE2462963A patent/DE2462963C2/de not_active Expired
- 1974-08-16 DD DD180545A patent/DD113756A5/xx unknown
- 1974-08-19 RO RO7491734A patent/RO70534A/ro unknown
- 1974-08-19 RO RO79830A patent/RO72882B/ro unknown
- 1974-08-19 RO RO7491735A patent/RO70535A/ro unknown
- 1974-08-20 NL NL7411092A patent/NL7411092A/xx unknown
- 1974-08-20 LU LU70764A patent/LU70764A1/xx unknown
- 1974-08-20 IN IN1864/CAL/1974A patent/IN140329B/en unknown
- 1974-08-21 FI FI2462/74A patent/FI61879C/fi active
- 1974-08-21 SE SE7410636A patent/SE394429B/xx not_active IP Right Cessation
- 1974-08-21 CA CA207,472A patent/CA1050556A/en not_active Expired
- 1974-08-21 CH CH1142674A patent/CH605741A5/xx not_active IP Right Cessation
- 1974-08-21 HU HULE754A patent/HU169728B/hu not_active IP Right Cessation
- 1974-08-21 SU SU742055571A patent/SU843738A3/ru active
- 1974-08-21 JP JP9600974A patent/JPS5328914B2/ja not_active Expired
- 1974-08-21 DK DK445974A patent/DK156391C/da active
- 1974-08-22 ES ES429446A patent/ES429446A1/es not_active Expired
- 1974-08-22 PL PL1974173617A patent/PL95235B1/pl unknown
- 1974-08-22 FR FR7428894A patent/FR2241308B1/fr not_active Expired
- 1974-08-22 PL PL1974189700A patent/PL96806B1/pl unknown
- 1974-08-22 AT AT684774A patent/AT336600B/de not_active IP Right Cessation
- 1974-08-22 BE BE147818A patent/BE819088A/xx not_active IP Right Cessation
- 1974-08-22 CS CS745833A patent/CS188201B2/cs unknown
- 1974-08-27 AR AR255253A patent/AR210246A1/es active
-
1976
- 1976-06-03 AR AR263502A patent/AR210132A1/es active
- 1976-06-03 AR AR263503A patent/AR210133A1/es active
- 1976-07-01 ES ES449425A patent/ES449425A1/es not_active Expired
- 1976-07-01 ES ES449426A patent/ES449426A1/es not_active Expired
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