NO802528L - Fremgangsmaate ved fremstilling av antiinflammatorisk aktive 4,5-diaryl-alfa-polyfluoralkyl-1h pyrrol-2-methanoler og 1-(4,5-diaryl-1h-pyrrol-2-yl)polyfluoralkanoner - Google Patents
Fremgangsmaate ved fremstilling av antiinflammatorisk aktive 4,5-diaryl-alfa-polyfluoralkyl-1h pyrrol-2-methanoler og 1-(4,5-diaryl-1h-pyrrol-2-yl)polyfluoralkanonerInfo
- Publication number
- NO802528L NO802528L NO802528A NO802528A NO802528L NO 802528 L NO802528 L NO 802528L NO 802528 A NO802528 A NO 802528A NO 802528 A NO802528 A NO 802528A NO 802528 L NO802528 L NO 802528L
- Authority
- NO
- Norway
- Prior art keywords
- alkyl
- compounds
- bis
- methyl
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 37
- 150000001875 compounds Chemical class 0.000 claims description 53
- 229910052731 fluorine Inorganic materials 0.000 claims description 32
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 20
- 238000002360 preparation method Methods 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 11
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 230000002152 alkylating effect Effects 0.000 claims description 5
- 150000002576 ketones Chemical class 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000001589 carboacyl group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 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 2
- 239000003377 acid catalyst Substances 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 150000004677 hydrates Chemical class 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 125000002524 organometallic group Chemical group 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 60
- 239000000203 mixture Substances 0.000 description 49
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- 239000000047 product Substances 0.000 description 29
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 238000004458 analytical method Methods 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 238000010992 reflux Methods 0.000 description 16
- 239000004480 active ingredient Substances 0.000 description 15
- 230000003110 anti-inflammatory effect Effects 0.000 description 14
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- 206010003246 arthritis Diseases 0.000 description 12
- 239000007787 solid Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 9
- 239000003921 oil Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- -1 pyrrole trifluoromethyl ketones Chemical class 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
- 239000003814 drug Substances 0.000 description 7
- 210000002683 foot Anatomy 0.000 description 7
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 7
- SNZAEUWCEHDROX-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-one;trihydrate Chemical compound O.O.O.FC(F)(F)C(=O)C(F)(F)F SNZAEUWCEHDROX-UHFFFAOYSA-N 0.000 description 6
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 238000004587 chromatography analysis Methods 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
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000002390 rotary evaporation Methods 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- VNMNSTIGSQBDPI-UHFFFAOYSA-N 2,3-diphenyl-1h-pyrrole Chemical compound N1C=CC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 VNMNSTIGSQBDPI-UHFFFAOYSA-N 0.000 description 5
- 208000002193 Pain Diseases 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
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- 239000010410 layer Substances 0.000 description 5
- 238000002953 preparative HPLC Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 230000029936 alkylation Effects 0.000 description 4
- 238000005804 alkylation reaction Methods 0.000 description 4
- 230000000202 analgesic effect Effects 0.000 description 4
- 230000002917 arthritic effect Effects 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000012259 ether extract Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 239000011343 solid material Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- ZJLFQMPKNLVRFB-UHFFFAOYSA-N 1-[4,5-bis(4-methoxyphenyl)-1h-pyrrol-2-yl]-2,2,2-trifluoroethanol Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC(C(O)C(F)(F)F)=C1 ZJLFQMPKNLVRFB-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
- 206010061218 Inflammation Diseases 0.000 description 3
- 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 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229940121363 anti-inflammatory agent Drugs 0.000 description 3
- 239000002260 anti-inflammatory agent Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
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- 210000000548 hind-foot Anatomy 0.000 description 3
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- 230000004054 inflammatory process Effects 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
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- 239000008297 liquid dosage form Substances 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- LXCFILQKKLGQFO-UHFFFAOYSA-N p-hydroxybenzoic acid methyl ester Natural products COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- DJLQKTWEKGXVCX-UHFFFAOYSA-N 1-(3-chloro-2-methylprop-1-enyl)-4-fluorobenzene Chemical compound ClCC(C)=CC1=CC=C(F)C=C1 DJLQKTWEKGXVCX-UHFFFAOYSA-N 0.000 description 2
- RMCRXSBPUSNZJR-UHFFFAOYSA-N 1-[4,5-bis(4-fluorophenyl)-1h-pyrrol-2-yl]-2,2,2-trifluoroethanol Chemical compound N1C(C(O)C(F)(F)F)=CC(C=2C=CC(F)=CC=2)=C1C1=CC=C(F)C=C1 RMCRXSBPUSNZJR-UHFFFAOYSA-N 0.000 description 2
- VGJWVEYTYIBXIA-UHFFFAOYSA-N 2,2,2-trifluoroethane-1,1-diol Chemical compound OC(O)C(F)(F)F VGJWVEYTYIBXIA-UHFFFAOYSA-N 0.000 description 2
- FPBVILRCRVYICY-UHFFFAOYSA-N 2,3-bis(4-fluorophenyl)-1-methylpyrrole Chemical compound CN1C=CC(C=2C=CC(F)=CC=2)=C1C1=CC=C(F)C=C1 FPBVILRCRVYICY-UHFFFAOYSA-N 0.000 description 2
- VRXSNZCPFMTGBV-UHFFFAOYSA-N 2,3-bis(4-fluorophenyl)-4-methyl-1h-pyrrole Chemical compound CC1=CNC(C=2C=CC(F)=CC=2)=C1C1=CC=C(F)C=C1 VRXSNZCPFMTGBV-UHFFFAOYSA-N 0.000 description 2
- WGVQZBURQZKDBN-UHFFFAOYSA-N 2,3-bis(4-methoxyphenyl)-1h-pyrrole Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC=C1 WGVQZBURQZKDBN-UHFFFAOYSA-N 0.000 description 2
- WJYMBVJBSFMDLE-UHFFFAOYSA-N 2-(dimethylhydrazinylidene)acetaldehyde Chemical compound CN(C)N=CC=O WJYMBVJBSFMDLE-UHFFFAOYSA-N 0.000 description 2
- WKLGGJLDQOAAPU-UHFFFAOYSA-N 3-(4-fluorophenyl)-2-methylprop-2-en-1-amine Chemical compound NCC(C)=CC1=CC=C(F)C=C1 WKLGGJLDQOAAPU-UHFFFAOYSA-N 0.000 description 2
- IBGBVQURUWBTKN-UHFFFAOYSA-N 4,5-diphenyl-1h-pyrrole-2,3-dicarboxylic acid Chemical compound OC(=O)C1=C(C(=O)O)NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 IBGBVQURUWBTKN-UHFFFAOYSA-N 0.000 description 2
- ICZLPNASPRSAJT-UHFFFAOYSA-N 4-fluoro-n-[3-(4-fluorophenyl)-2-methylprop-2-enyl]benzamide Chemical compound C=1C=C(F)C=CC=1C=C(C)CNC(=O)C1=CC=C(F)C=C1 ICZLPNASPRSAJT-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- TUDKXMMYSLMVND-UHFFFAOYSA-N [1-(trifluoromethyl)pyrrol-2-yl]methanol Chemical compound OCC1=CC=CN1C(F)(F)F TUDKXMMYSLMVND-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
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- 238000000498 ball milling Methods 0.000 description 2
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- 239000000969 carrier Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
- 238000006114 decarboxylation reaction Methods 0.000 description 2
- 230000003111 delayed effect Effects 0.000 description 2
- VQMOVERDZSFLOQ-UHFFFAOYSA-N dimethyl 4,5-diphenyl-1h-pyrrole-2,3-dicarboxylate Chemical compound COC(=O)C1=C(C(=O)OC)NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 VQMOVERDZSFLOQ-UHFFFAOYSA-N 0.000 description 2
- VHILMKFSCRWWIJ-UHFFFAOYSA-N dimethyl acetylenedicarboxylate Chemical compound COC(=O)C#CC(=O)OC VHILMKFSCRWWIJ-UHFFFAOYSA-N 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- HTSROGFJSMXEFJ-UHFFFAOYSA-N ethyl 4,5-diphenyl-1h-pyrrole-3-carboxylate Chemical compound CCOC(=O)C1=CNC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 HTSROGFJSMXEFJ-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
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- 239000011737 fluorine Substances 0.000 description 2
- 150000004795 grignard reagents Chemical class 0.000 description 2
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- 238000002329 infrared spectrum Methods 0.000 description 2
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- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
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- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- XDIYNQZUNSSENW-UUBOPVPUSA-N (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O XDIYNQZUNSSENW-UUBOPVPUSA-N 0.000 description 1
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- OTKCEEWUXHVZQI-UHFFFAOYSA-N 1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(=O)CC1=CC=CC=C1 OTKCEEWUXHVZQI-UHFFFAOYSA-N 0.000 description 1
- ZSYSFTJSRLJSOD-UHFFFAOYSA-N 1-[4,5-bis(4-fluorophenyl)-1h-pyrrol-2-yl]-2,2,3,3,3-pentafluoropropan-1-one Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=CC(F)=CC=2)NC(C(=O)C(F)(F)C(F)(F)F)=C1 ZSYSFTJSRLJSOD-UHFFFAOYSA-N 0.000 description 1
- BULRPSMQHLOYEZ-UHFFFAOYSA-N 1-[4,5-bis(4-methoxyphenyl)-1h-pyrrol-2-yl]-2,2,2-trifluoroethanone Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC(C(=O)C(F)(F)F)=C1 BULRPSMQHLOYEZ-UHFFFAOYSA-N 0.000 description 1
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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
- C07D207/32—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/323—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
-
- 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
- C07D207/32—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- C07D207/32—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/333—Radicals substituted by oxygen or sulfur atoms
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7032679A | 1979-08-27 | 1979-08-27 | |
| US15923880A | 1980-06-20 | 1980-06-20 | |
| US15923780A | 1980-06-20 | 1980-06-20 | |
| US16680780A | 1980-07-17 | 1980-07-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO802528L true NO802528L (no) | 1981-03-02 |
Family
ID=27490817
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO802528A NO802528L (no) | 1979-08-27 | 1980-08-26 | Fremgangsmaate ved fremstilling av antiinflammatorisk aktive 4,5-diaryl-alfa-polyfluoralkyl-1h pyrrol-2-methanoler og 1-(4,5-diaryl-1h-pyrrol-2-yl)polyfluoralkanoner |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP0025884A1 (da) |
| DK (1) | DK350280A (da) |
| ES (1) | ES8106498A1 (da) |
| FI (1) | FI802693A7 (da) |
| GR (1) | GR69839B (da) |
| IL (1) | IL60917A0 (da) |
| NO (1) | NO802528L (da) |
| PT (1) | PT71748B (da) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4267190A (en) * | 1980-04-18 | 1981-05-12 | E. I. Du Pont De Nemours And Company | Antiinflammatory 4,5-diaryl-α,α-bis(polyfluoromethyl)-1H-pyrrole-2-methanethiols |
| EP0044485A1 (en) * | 1980-07-21 | 1982-01-27 | E.I. Du Pont De Nemours And Company | Antiinflammatory 2,3-diaryl-5(2,2,2-trifluoro-1-(trifluoromethyl)-ethyl)-1H-pyrroles |
| US6100392A (en) * | 1992-08-14 | 2000-08-08 | The Trustees Of The University Of Pennsylavania | Electron-deficient porphyrins and processes and intermediates for preparing same |
| US5599924A (en) * | 1992-08-14 | 1997-02-04 | Trustees Of The University Of Pennsylvania | Electron-deficient porphyrins and processes and intermediates for preparing same |
| US5837719A (en) * | 1995-08-10 | 1998-11-17 | Merck & Co., Inc. | 2,5-substituted aryl pyrroles, compositions containing such compounds and methods of use |
| US5792778A (en) * | 1995-08-10 | 1998-08-11 | Merck & Co., Inc. | 2-substituted aryl pyrroles, compositions containing such compounds and methods of use |
| US5776954A (en) * | 1996-10-30 | 1998-07-07 | Merck & Co., Inc. | Substituted pyridyl pyrroles, compositions containing such compounds and methods of use |
| CA2316953A1 (en) | 1997-12-26 | 1999-07-08 | Nissin Food Products Co., Ltd. | 5-arylpyrrole derivatives |
| GB0711776D0 (en) * | 2007-06-18 | 2007-07-25 | Syngenta Participations Ag | Substituted aromatic heterocyclic compounds as fungicides |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3197480A (en) * | 1962-12-12 | 1965-07-27 | Du Pont | 2 and 2, 4-(alpha hydroxypolyperhalocycloalkyl)-thiophenes, pyrroles, and furans; 2 and 2, 4-[(alpha hydroxyalpha, alpha dipolyperhalo hydrocarbon) methyl]-thiophenes, pyrroles and furans and process for making them |
| US3709906A (en) * | 1968-07-26 | 1973-01-09 | Sankyo Co | 2-alkyl-4,5-diphenylpyrrole derivatives |
| US3918954A (en) * | 1973-03-11 | 1975-11-11 | Sterling Drug Inc | Herbicidal compositions containing halomethyl ketones and method of use thereof |
| DK75779A (da) * | 1978-03-13 | 1979-09-14 | Du Pont | 4,5-diaryl-2- (substitueret thio) pyrroler og sulfoxider og sulfoner deraf samt fremgangsmaader til deres fremstilling og anvendelse |
-
1980
- 1980-08-13 DK DK350280A patent/DK350280A/da unknown
- 1980-08-22 EP EP80105006A patent/EP0025884A1/en not_active Withdrawn
- 1980-08-26 NO NO802528A patent/NO802528L/no unknown
- 1980-08-26 IL IL60917A patent/IL60917A0/xx unknown
- 1980-08-26 GR GR62753A patent/GR69839B/el unknown
- 1980-08-26 FI FI802693A patent/FI802693A7/fi not_active Application Discontinuation
- 1980-08-27 PT PT71748A patent/PT71748B/pt unknown
- 1980-08-27 ES ES494546A patent/ES8106498A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FI802693A7 (fi) | 1981-01-01 |
| PT71748B (en) | 1982-04-07 |
| PT71748A (en) | 1980-09-01 |
| ES494546A0 (es) | 1981-07-01 |
| EP0025884A1 (en) | 1981-04-01 |
| IL60917A0 (en) | 1980-10-26 |
| DK350280A (da) | 1981-02-28 |
| ES8106498A1 (es) | 1981-07-01 |
| GR69839B (da) | 1982-07-19 |
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