FI61879C - Analogifoerfarande foer framstaellning av nya terapeutiskt effektiva aminopyrrolderivat - Google Patents
Analogifoerfarande foer framstaellning av nya terapeutiskt effektiva aminopyrrolderivat Download PDFInfo
- Publication number
- FI61879C FI61879C FI2462/74A FI246274A FI61879C FI 61879 C FI61879 C FI 61879C FI 2462/74 A FI2462/74 A FI 2462/74A FI 246274 A FI246274 A FI 246274A FI 61879 C FI61879 C FI 61879C
- Authority
- FI
- Finland
- Prior art keywords
- compound
- alkyl
- amino
- formula
- phenyl
- Prior art date
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- 230000001225 therapeutic effect Effects 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 118
- -1 carboxy, carbamyl Chemical group 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 12
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 9
- QLSWIGRIBOSFMV-UHFFFAOYSA-N 1h-pyrrol-2-amine Chemical class NC1=CC=CN1 QLSWIGRIBOSFMV-UHFFFAOYSA-N 0.000 claims description 7
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 150000003254 radicals Chemical class 0.000 claims description 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- 125000005219 aminonitrile group Chemical group 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 210000003169 central nervous system Anatomy 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 238000005903 acid hydrolysis reaction Methods 0.000 claims 2
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 206010061218 Inflammation Diseases 0.000 claims 1
- 125000005079 alkoxycarbonylmethyl group Chemical group 0.000 claims 1
- 125000001118 alkylidene group Chemical group 0.000 claims 1
- 150000001412 amines Chemical group 0.000 claims 1
- XDGYHAAUHYNDMA-UHFFFAOYSA-N benzyl hypochlorite Chemical compound ClOCC1=CC=CC=C1 XDGYHAAUHYNDMA-UHFFFAOYSA-N 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 106
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 103
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 93
- 239000000543 intermediate Substances 0.000 description 28
- 239000000243 solution Substances 0.000 description 24
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 22
- JTIHSSVKTWPPHI-UHFFFAOYSA-N 2-amino-2-phenylacetonitrile Chemical compound N#CC(N)C1=CC=CC=C1 JTIHSSVKTWPPHI-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 11
- 239000002904 solvent Substances 0.000 description 10
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 241000700159 Rattus Species 0.000 description 8
- 239000012458 free base Substances 0.000 description 7
- 239000000155 melt Substances 0.000 description 7
- 206010030113 Oedema Diseases 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- VHILMKFSCRWWIJ-UHFFFAOYSA-N dimethyl acetylenedicarboxylate Chemical group COC(=O)C#CC(=O)OC VHILMKFSCRWWIJ-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- 238000007363 ring formation reaction Methods 0.000 description 5
- 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 description 4
- 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 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 229960002895 phenylbutazone Drugs 0.000 description 4
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- CVBUKMMMRLOKQR-UHFFFAOYSA-N 1-phenylbutane-1,3-dione Chemical compound CC(=O)CC(=O)C1=CC=CC=C1 CVBUKMMMRLOKQR-UHFFFAOYSA-N 0.000 description 3
- 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 description 3
- DQQIUVCNBOJDGF-UHFFFAOYSA-N 2-aminobutanenitrile Chemical compound CCC(N)C#N DQQIUVCNBOJDGF-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
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- DFNYGALUNNFWKJ-UHFFFAOYSA-N aminoacetonitrile Chemical compound NCC#N DFNYGALUNNFWKJ-UHFFFAOYSA-N 0.000 description 3
- 230000000202 analgesic effect Effects 0.000 description 3
- 239000002260 anti-inflammatory agent Substances 0.000 description 3
- 229940121363 anti-inflammatory agent Drugs 0.000 description 3
- 230000001143 conditioned effect Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 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 description 2
- 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 description 2
- PKQIDSVLSKFZQC-UHFFFAOYSA-N 3-oxobutanal Chemical compound CC(=O)CC=O PKQIDSVLSKFZQC-UHFFFAOYSA-N 0.000 description 2
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 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 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 229960001138 acetylsalicylic acid Drugs 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- 230000001754 anti-pyretic effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 239000012050 conventional carrier Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- HTDQDSYQINAWAG-UHFFFAOYSA-N dimethyl 4-amino-5-phenyl-1h-pyrrole-2,3-dicarboxylate;hydrochloride Chemical compound Cl.COC(=O)C1=C(C(=O)OC)NC(C=2C=CC=CC=2)=C1N HTDQDSYQINAWAG-UHFFFAOYSA-N 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- MWVFCEVNXHTDNF-UHFFFAOYSA-N hexane-2,3-dione Chemical compound CCCC(=O)C(C)=O MWVFCEVNXHTDNF-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229960004815 meprobamate Drugs 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000932 sedative agent Substances 0.000 description 2
- 230000001624 sedative effect Effects 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- PKXNZRBSMDMMGF-UHFFFAOYSA-N (4-amino-2-methyl-5-phenyl-1h-pyrrol-3-yl)-phenylmethanone;hydrochloride Chemical compound Cl.CC=1NC(C=2C=CC=CC=2)=C(N)C=1C(=O)C1=CC=CC=C1 PKXNZRBSMDMMGF-UHFFFAOYSA-N 0.000 description 1
- DKXUQKDQLJULKZ-UHFFFAOYSA-N (4-amino-5-phenyl-1h-pyrrol-3-yl)-phenylmethanone;hydrochloride Chemical compound Cl.NC=1C(C(=O)C=2C=CC=CC=2)=CNC=1C1=CC=CC=C1 DKXUQKDQLJULKZ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- CYPYOGOPKDBEFY-UHFFFAOYSA-N 1-(2-chlorophenyl)butane-1,3-dione Chemical compound CC(=O)CC(=O)C1=CC=CC=C1Cl CYPYOGOPKDBEFY-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- CTUFIXJQAWGDQP-UHFFFAOYSA-N 1-(4-amino-1-ethyl-2-methyl-5-phenylpyrrol-3-yl)ethanone Chemical compound CCN1C(C)=C(C(C)=O)C(N)=C1C1=CC=CC=C1 CTUFIXJQAWGDQP-UHFFFAOYSA-N 0.000 description 1
- UWQCNBNODRCNIV-UHFFFAOYSA-N 1-(4-amino-2-methyl-5-phenyl-1-propylpyrrol-3-yl)ethanone Chemical compound CCCN1C(C)=C(C(C)=O)C(N)=C1C1=CC=CC=C1 UWQCNBNODRCNIV-UHFFFAOYSA-N 0.000 description 1
- ABFIFFIBZHIQCH-UHFFFAOYSA-N 1-(4-amino-5-ethyl-2-methyl-1h-pyrrol-3-yl)ethanone;hydrochloride Chemical compound Cl.CCC=1NC(C)=C(C(C)=O)C=1N ABFIFFIBZHIQCH-UHFFFAOYSA-N 0.000 description 1
- PVCFQGTUBKQIMH-UHFFFAOYSA-N 1-(4-methoxyphenyl)butane-1,3-dione Chemical compound COC1=CC=C(C(=O)CC(C)=O)C=C1 PVCFQGTUBKQIMH-UHFFFAOYSA-N 0.000 description 1
- MLFFAHVRUAJXRJ-UHFFFAOYSA-N 1-[4-(benzylideneamino)-1,2-dimethyl-5-phenylpyrrol-3-yl]ethanone Chemical group CC(=O)C1=C(C)N(C)C(C=2C=CC=CC=2)=C1N=CC1=CC=CC=C1 MLFFAHVRUAJXRJ-UHFFFAOYSA-N 0.000 description 1
- COWHWUFNJDEMFD-UHFFFAOYSA-N 1-[4-(benzylideneamino)-2-methyl-5-phenyl-1-propylpyrrol-3-yl]ethanone Chemical compound C=1C=CC=CC=1C=1N(CCC)C(C)=C(C(C)=O)C=1N=CC1=CC=CC=C1 COWHWUFNJDEMFD-UHFFFAOYSA-N 0.000 description 1
- FAFLULXKPKCSPT-UHFFFAOYSA-N 1-[4-amino-5-(4-hydroxyphenyl)-2-methyl-1h-pyrrol-3-yl]ethanone Chemical compound CC(=O)C1=C(C)NC(C=2C=CC(O)=CC=2)=C1N FAFLULXKPKCSPT-UHFFFAOYSA-N 0.000 description 1
- JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
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- 125000006280 2-bromobenzyl group Chemical group [H]C1=C([H])C(Br)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical group [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- 125000006279 3-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Br)=C1[H])C([H])([H])* 0.000 description 1
- HCSDAMGBOVWGEO-UHFFFAOYSA-N 3-oxo-3-phenylpropanal Chemical compound O=CCC(=O)C1=CC=CC=C1 HCSDAMGBOVWGEO-UHFFFAOYSA-N 0.000 description 1
- MGBGYHHKTBCNLO-UHFFFAOYSA-N 4-amino-2-methoxycarbonyl-5-phenyl-1H-pyrrole-3-carboxylic acid Chemical compound NC1=C(NC(=C1C(=O)O)C(=O)OC)C1=CC=CC=C1 MGBGYHHKTBCNLO-UHFFFAOYSA-N 0.000 description 1
- RUMUWPDIVPUMCK-UHFFFAOYSA-N 4-amino-2-methyl-5-phenyl-1h-pyrrole-3-carboxamide;hydrochloride Chemical compound Cl.NC(=O)C1=C(C)NC(C=2C=CC=CC=2)=C1N RUMUWPDIVPUMCK-UHFFFAOYSA-N 0.000 description 1
- RSWSDYFCSZZARK-UHFFFAOYSA-N 4-amino-2-methyl-n,5-diphenyl-1h-pyrrole-3-carboxamide Chemical compound CC=1NC(C=2C=CC=CC=2)=C(N)C=1C(=O)NC1=CC=CC=C1 RSWSDYFCSZZARK-UHFFFAOYSA-N 0.000 description 1
- QNOVAYFCBLSPKS-UHFFFAOYSA-N 4-amino-3-methoxycarbonyl-5-phenyl-1H-pyrrole-2-carboxylic acid Chemical compound NC1=C(NC(=C1C(=O)OC)C(=O)O)C1=CC=CC=C1 QNOVAYFCBLSPKS-UHFFFAOYSA-N 0.000 description 1
- MZNBDOJDYMYLBA-UHFFFAOYSA-N 4-amino-5-phenyl-1H-pyrrole-2,3-dicarboxylic acid Chemical compound NC1=C(NC(=C1C(=O)O)C(=O)O)C1=CC=CC=C1 MZNBDOJDYMYLBA-UHFFFAOYSA-N 0.000 description 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- JNMYDBVVZZQLDS-UHFFFAOYSA-N 4-tert-butyl-1,2-diphenylpyrazolidine-3,5-dione Chemical compound O=C1C(C(C)(C)C)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 JNMYDBVVZZQLDS-UHFFFAOYSA-N 0.000 description 1
- IZCBXLKODYZSDJ-UHFFFAOYSA-N 5-methylhexan-2-amine Chemical compound CC(C)CCC(C)N IZCBXLKODYZSDJ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- QGTBYNRSUKXSQE-UHFFFAOYSA-N C(C)(=O)C=1C(=C(N(C1C)CC1=CC=C(C=C1)Cl)C1=CC=CC=C1)N=CC1=CC=CC=C1.C(C)(=O)C=1C(=C(N(C1C)CC1=CC=C(C=C1)Cl)C1=CC=CC=C1)N Chemical compound C(C)(=O)C=1C(=C(N(C1C)CC1=CC=C(C=C1)Cl)C1=CC=CC=C1)N=CC1=CC=CC=C1.C(C)(=O)C=1C(=C(N(C1C)CC1=CC=C(C=C1)Cl)C1=CC=CC=C1)N QGTBYNRSUKXSQE-UHFFFAOYSA-N 0.000 description 1
- VNFMMLZEEWXXDW-UHFFFAOYSA-N CC1=CC(=C(N1C(=O)C2=CC=C(C=C2)OC)C3=CC=CC=C3)N Chemical compound CC1=CC(=C(N1C(=O)C2=CC=C(C=C2)OC)C3=CC=CC=C3)N VNFMMLZEEWXXDW-UHFFFAOYSA-N 0.000 description 1
- NGTRWBYNSJIGKA-UHFFFAOYSA-N CC1=CC=C(N1)C(=O)C(CN)C2=CC=CC=C2 Chemical compound CC1=CC=C(N1)C(=O)C(CN)C2=CC=CC=C2 NGTRWBYNSJIGKA-UHFFFAOYSA-N 0.000 description 1
- 241000283153 Cetacea Species 0.000 description 1
- 241000251730 Chondrichthyes Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- FXSGPIAXMFXVOX-UHFFFAOYSA-N N-(4-benzoyl-5-methyl-2-phenyl-1H-pyrrol-3-yl)acetamide Chemical compound C(C)(=O)NC1=C(NC(=C1C(C1=CC=CC=C1)=O)C)C1=CC=CC=C1 FXSGPIAXMFXVOX-UHFFFAOYSA-N 0.000 description 1
- ATWLCPHWYPSRBQ-UHFFFAOYSA-N N-Methylacetoacetamide Chemical compound CNC(=O)CC(C)=O ATWLCPHWYPSRBQ-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- OGSYCVCLXAFDNE-UHFFFAOYSA-N [cyano(phenyl)methyl]azanium;chloride Chemical compound [Cl-].N#CC([NH3+])C1=CC=CC=C1 OGSYCVCLXAFDNE-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 239000000679 carrageenan Substances 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 229940113118 carrageenan Drugs 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 239000003874 central nervous system depressant Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000009194 climbing Effects 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- ZHGASCUQXLPSDT-UHFFFAOYSA-N cyclohexanesulfonic acid Chemical class OS(=O)(=O)C1CCCCC1 ZHGASCUQXLPSDT-UHFFFAOYSA-N 0.000 description 1
- 125000004989 dicarbonyl group Chemical group 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- ZSANYRMTSBBUCA-UHFFFAOYSA-N diethyl 3-oxopentanedioate Chemical compound CCOC(=O)CC(=O)CC(=O)OCC ZSANYRMTSBBUCA-UHFFFAOYSA-N 0.000 description 1
- GWNHEKOSAREZSV-UHFFFAOYSA-N diethyl 4-amino-5-phenyl-1h-pyrrole-2,3-dicarboxylate;hydrochloride Chemical compound Cl.CCOC(=O)C1=C(C(=O)OCC)NC(C=2C=CC=CC=2)=C1N GWNHEKOSAREZSV-UHFFFAOYSA-N 0.000 description 1
- STRNXFOUBFLVIN-UHFFFAOYSA-N diethyl but-2-ynedioate Chemical group CCOC(=O)C#CC(=O)OCC STRNXFOUBFLVIN-UHFFFAOYSA-N 0.000 description 1
- PCJCEHMWLCGMPM-UHFFFAOYSA-N dimethyl 4-amino-5-(4-methoxyphenyl)-1h-pyrrole-2,3-dicarboxylate;hydrochloride Chemical compound Cl.COC(=O)C1=C(C(=O)OC)NC(C=2C=CC(OC)=CC=2)=C1N PCJCEHMWLCGMPM-UHFFFAOYSA-N 0.000 description 1
- XPDMSHLNEFVTQS-UHFFFAOYSA-N dimethyl 4-amino-5-ethyl-1h-pyrrole-2,3-dicarboxylate;hydrochloride Chemical compound Cl.CCC=1NC(C(=O)OC)=C(C(=O)OC)C=1N XPDMSHLNEFVTQS-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- UVJQQYMWMAISMQ-UHFFFAOYSA-N ethyl 2,4-dioxo-4-phenylbutanoate Chemical compound CCOC(=O)C(=O)CC(=O)C1=CC=CC=C1 UVJQQYMWMAISMQ-UHFFFAOYSA-N 0.000 description 1
- WDSVUWUXYSUOEX-UHFFFAOYSA-N ethyl 4-amino-5-phenyl-1h-pyrrole-3-carboxylate;hydrochloride Chemical compound Cl.CCOC(=O)C1=CNC(C=2C=CC=CC=2)=C1N WDSVUWUXYSUOEX-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- VHFBTKQOIBRGQP-UHFFFAOYSA-N fluoro nitrate Chemical group [O-][N+](=O)OF VHFBTKQOIBRGQP-UHFFFAOYSA-N 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 150000002466 imines Chemical group 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([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
- 239000007788 liquid Substances 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- STWAEDTWQPJPBY-UHFFFAOYSA-N methyl 4-amino-2-(hydrazinecarbonyl)-5-phenyl-1H-pyrrole-3-carboxylate Chemical compound NC1=C(NC(=C1C(=O)OC)C(NN)=O)C1=CC=CC=C1 STWAEDTWQPJPBY-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002123 temporal effect Effects 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
- VSRBKQFNFZQRBM-UHFFFAOYSA-N tuaminoheptane Chemical compound CCCCCC(C)N VSRBKQFNFZQRBM-UHFFFAOYSA-N 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Classifications
-
- 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3979073A GB1427945A (en) | 1973-08-22 | 1973-08-22 | Aminopyrrole derivatives |
| GB3979073 | 1973-08-22 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI246274A7 FI246274A7 (en, 2012) | 1975-02-23 |
| FI61879B FI61879B (fi) | 1982-06-30 |
| FI61879C true FI61879C (fi) | 1982-10-11 |
Family
ID=10411528
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI2462/74A FI61879C (fi) | 1973-08-22 | 1974-08-21 | Analogifoerfarande foer framstaellning av nya terapeutiskt effektiva aminopyrrolderivat |
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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