NO315554B1 - 4-Fenyl-pyridin-derivater, fremgangsmåte ved fremstilling og anvendelse derav, og medikament inneholdende slike derivater - Google Patents
4-Fenyl-pyridin-derivater, fremgangsmåte ved fremstilling og anvendelse derav, og medikament inneholdende slike derivater Download PDFInfo
- Publication number
- NO315554B1 NO315554B1 NO20000885A NO20000885A NO315554B1 NO 315554 B1 NO315554 B1 NO 315554B1 NO 20000885 A NO20000885 A NO 20000885A NO 20000885 A NO20000885 A NO 20000885A NO 315554 B1 NO315554 B1 NO 315554B1
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- trifluoromethyl
- bis
- tolyl
- phenyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 65
- 238000002360 preparation method Methods 0.000 title claims description 57
- 239000003814 drug Substances 0.000 title claims description 8
- 229940079593 drug Drugs 0.000 title claims description 4
- 150000005362 4-phenylpyridines Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 197
- FMQPGFVLWDLWPR-UHFFFAOYSA-N n-methyl-n-[(2-methylnaphthalen-1-yl)methyl]-4-(2-methylphenyl)-6-morpholin-4-ylpyridine-3-carboxamide Chemical compound CC=1C=CC2=CC=CC=C2C=1CN(C)C(=O)C1=CN=C(N2CCOCC2)C=C1C1=CC=CC=C1C FMQPGFVLWDLWPR-UHFFFAOYSA-N 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 20
- -1 cyclic tertiary amine Chemical class 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 229940047889 isobutyramide Drugs 0.000 claims description 12
- 229910052740 iodine Inorganic materials 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 150000002431 hydrogen Chemical group 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 102000002002 Neurokinin-1 Receptors Human genes 0.000 claims description 6
- 108010040718 Neurokinin-1 Receptors Proteins 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 6
- HZBSJCLPYPJTHM-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-n-methyl-4-(2-methylphenyl)-6-piperazin-1-ylpyridine-3-carboxamide Chemical compound C=1N=C(N2CCNCC2)C=C(C=2C(=CC=CC=2)C)C=1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 HZBSJCLPYPJTHM-UHFFFAOYSA-N 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- GTBUTLFXQOBLCG-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-n-methyl-4-(2-methylphenyl)pyridine-3-carboxamide Chemical group C=1N=CC=C(C=2C(=CC=CC=2)C)C=1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 GTBUTLFXQOBLCG-UHFFFAOYSA-N 0.000 claims description 5
- 230000009467 reduction Effects 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- BXXGEOWRMSJJAJ-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-6-[4-(cyanomethyl)piperazin-1-yl]-n-methyl-4-(2-methylphenyl)pyridine-3-carboxamide Chemical compound C=1N=C(N2CCN(CC#N)CC2)C=C(C=2C(=CC=CC=2)C)C=1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 BXXGEOWRMSJJAJ-UHFFFAOYSA-N 0.000 claims description 4
- HQMNLEYZUWNHDL-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-n-cyclopropyl-4-(2-methylphenyl)pyridine-3-carboxamide Chemical compound CC1=CC=CC=C1C1=CC=NC=C1C(=O)N(C1CC1)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 HQMNLEYZUWNHDL-UHFFFAOYSA-N 0.000 claims description 4
- 229940044551 receptor antagonist Drugs 0.000 claims description 4
- 239000002464 receptor antagonist Substances 0.000 claims description 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
- DSBGAUHQEXISAQ-UHFFFAOYSA-N 2-[3,5-bis(trifluoromethyl)phenyl]-n,2-dimethyl-n-[6-[methyl(2-morpholin-4-ylethyl)amino]-4-(2-methylphenyl)pyridin-3-yl]propanamide Chemical compound C=1C(C=2C(=CC=CC=2)C)=C(N(C)C(=O)C(C)(C)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C=NC=1N(C)CCN1CCOCC1 DSBGAUHQEXISAQ-UHFFFAOYSA-N 0.000 claims description 3
- IWQYMFHSVCMCNX-UHFFFAOYSA-N 2-[3,5-bis(trifluoromethyl)phenyl]-n-[6-[2-hydroxyethyl(methyl)amino]-4-(2-methylphenyl)pyridin-3-yl]-n,2-dimethylpropanamide Chemical compound C1=NC(N(CCO)C)=CC(C=2C(=CC=CC=2)C)=C1N(C)C(=O)C(C)(C)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 IWQYMFHSVCMCNX-UHFFFAOYSA-N 0.000 claims description 3
- KNWHGGDHNQZRAP-UHFFFAOYSA-N 6-[3-[acetyl(methyl)amino]pyrrolidin-1-yl]-n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-n-methyl-4-(2-methylphenyl)pyridine-3-carboxamide Chemical compound C=1N=C(N2CC(CC2)N(C)C(C)=O)C=C(C=2C(=CC=CC=2)C)C=1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 KNWHGGDHNQZRAP-UHFFFAOYSA-N 0.000 claims description 3
- DFPAKSUCGFBDDF-ZQBYOMGUSA-N [14c]-nicotinamide Chemical compound N[14C](=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-ZQBYOMGUSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- OFNUQLHUVSTYKN-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-4-(2-fluorophenyl)-n-methylpyridine-3-carboxamide Chemical compound C=1N=CC=C(C=2C(=CC=CC=2)F)C=1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 OFNUQLHUVSTYKN-UHFFFAOYSA-N 0.000 claims description 3
- WLFSWIPBWCLJIG-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-6-[4-(2-hydroxyethyl)piperazin-1-yl]-n-methyl-4-(2-methylphenyl)pyridine-3-carboxamide Chemical compound C=1N=C(N2CCN(CCO)CC2)C=C(C=2C(=CC=CC=2)C)C=1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 WLFSWIPBWCLJIG-UHFFFAOYSA-N 0.000 claims description 3
- DGRVWNYJJZUMSS-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-n-methyl-4-(2-methylphenyl)-6-morpholin-4-ylpyridine-3-carboxamide Chemical compound C=1N=C(N2CCOCC2)C=C(C=2C(=CC=CC=2)C)C=1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 DGRVWNYJJZUMSS-UHFFFAOYSA-N 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- 125000005988 1,1-dioxo-thiomorpholinyl group Chemical group 0.000 claims description 2
- 125000005987 1-oxo-thiomorpholinyl group Chemical group 0.000 claims description 2
- WSLIVRZOMVURHI-UHFFFAOYSA-N 2-[3,5-bis(trifluoromethyl)phenyl]-2-methyl-n-[4-(2-methylphenyl)-6-morpholin-4-ylpyridin-3-yl]propanamide Chemical compound CC1=CC=CC=C1C1=CC(N2CCOCC2)=NC=C1NC(=O)C(C)(C)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 WSLIVRZOMVURHI-UHFFFAOYSA-N 0.000 claims description 2
- ZGNPLCMMVKCTHM-UHFFFAOYSA-N 2-[3,5-bis(trifluoromethyl)phenyl]-n,2-dimethyl-n-[4-(2-methylphenyl)-6-morpholin-4-ylpyridin-3-yl]propanamide Chemical compound C=1N=C(N2CCOCC2)C=C(C=2C(=CC=CC=2)C)C=1N(C)C(=O)C(C)(C)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 ZGNPLCMMVKCTHM-UHFFFAOYSA-N 0.000 claims description 2
- GVDRTZQXERUDPE-UHFFFAOYSA-N 2-[3,5-bis(trifluoromethyl)phenyl]-n-[4-(2-chlorophenyl)-6-morpholin-4-ylpyridin-3-yl]-n,2-dimethylpropanamide Chemical compound C=1N=C(N2CCOCC2)C=C(C=2C(=CC=CC=2)Cl)C=1N(C)C(=O)C(C)(C)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 GVDRTZQXERUDPE-UHFFFAOYSA-N 0.000 claims description 2
- MVEWHIDMBLIQIL-UHFFFAOYSA-N 2-[3,5-bis(trifluoromethyl)phenyl]-n-[4-(2-chlorophenyl)pyridin-3-yl]-n,2-dimethylpropanamide Chemical compound C=1N=CC=C(C=2C(=CC=CC=2)Cl)C=1N(C)C(=O)C(C)(C)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 MVEWHIDMBLIQIL-UHFFFAOYSA-N 0.000 claims description 2
- AHHIIEQZKJBQFY-UHFFFAOYSA-N 2-[3,5-bis(trifluoromethyl)phenyl]-n-methyl-n-[4-(2-methylphenyl)-6-morpholin-4-ylpyridin-3-yl]acetamide Chemical compound C=1N=C(N2CCOCC2)C=C(C=2C(=CC=CC=2)C)C=1N(C)C(=O)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 AHHIIEQZKJBQFY-UHFFFAOYSA-N 0.000 claims description 2
- RKPZFEFLRSLJGS-UHFFFAOYSA-N 2-[3,5-bis(trifluoromethyl)phenyl]-n-methyl-n-[4-(2-methylphenyl)pyridin-3-yl]propanamide Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1C(C)C(=O)N(C)C1=CN=CC=C1C1=CC=CC=C1C RKPZFEFLRSLJGS-UHFFFAOYSA-N 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 230000004048 modification Effects 0.000 claims description 2
- 238000012986 modification Methods 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- XTUGEGDIPNFCHX-UHFFFAOYSA-N n-[2-[3,5-bis(trifluoromethyl)phenyl]-2-methylpropyl]-4-(4-fluoro-2-methylphenyl)-n-methyl-6-(4-methylpiperazin-1-yl)pyridin-3-amine Chemical compound C=1N=C(N2CCN(C)CC2)C=C(C=2C(=CC(F)=CC=2)C)C=1N(C)CC(C)(C)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 XTUGEGDIPNFCHX-UHFFFAOYSA-N 0.000 claims description 2
- LXCMOQGQIBFNJJ-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-4-(2-methoxyphenyl)-n-methylpyridine-3-carboxamide Chemical compound COC1=CC=CC=C1C1=CC=NC=C1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 LXCMOQGQIBFNJJ-UHFFFAOYSA-N 0.000 claims description 2
- VQHCPDADMQPSJL-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-6-[4-[2-(2-hydroxyethoxy)ethyl]piperazin-1-yl]-n-methyl-4-(2-methylphenyl)pyridine-3-carboxamide Chemical compound C=1N=C(N2CCN(CCOCCO)CC2)C=C(C=2C(=CC=CC=2)C)C=1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 VQHCPDADMQPSJL-UHFFFAOYSA-N 0.000 claims description 2
- FNGXRBAWNZYBIM-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-n-ethyl-4-(2-methylphenyl)pyridine-3-carboxamide Chemical compound C=1N=CC=C(C=2C(=CC=CC=2)C)C=1C(=O)N(CC)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 FNGXRBAWNZYBIM-UHFFFAOYSA-N 0.000 claims description 2
- NMKPCQAGMKTXDX-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-n-methyl-4-(2-methylphenyl)-6-[4-(1,2,4-oxadiazol-3-ylmethyl)piperazin-1-yl]pyridine-3-carboxamide Chemical compound C=1N=C(N2CCN(CC3=NOC=N3)CC2)C=C(C=2C(=CC=CC=2)C)C=1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 NMKPCQAGMKTXDX-UHFFFAOYSA-N 0.000 claims description 2
- AQWUNPJYAREFTL-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-n-methyl-4-[2-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound C=1N=CC=C(C=2C(=CC=CC=2)C(F)(F)F)C=1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 AQWUNPJYAREFTL-UHFFFAOYSA-N 0.000 claims description 2
- ZFUYBRRKEVIJEB-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-n-methyl-6-(4-methylpiperazin-1-yl)-4-naphthalen-1-ylpyridine-3-carboxamide Chemical compound C=1N=C(N2CCN(C)CC2)C=C(C=2C3=CC=CC=C3C=CC=2)C=1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 ZFUYBRRKEVIJEB-UHFFFAOYSA-N 0.000 claims description 2
- OWUNCEWWOVCUJX-UHFFFAOYSA-N n-benzyl-4-phenylpyridine-3-carboxamide Chemical compound C=1N=CC=C(C=2C=CC=CC=2)C=1C(=O)NCC1=CC=CC=C1 OWUNCEWWOVCUJX-UHFFFAOYSA-N 0.000 claims description 2
- WAXQNWCZJDTGBU-UHFFFAOYSA-N netupitant Chemical group C=1N=C(N2CCN(C)CC2)C=C(C=2C(=CC=CC=2)C)C=1N(C)C(=O)C(C)(C)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 WAXQNWCZJDTGBU-UHFFFAOYSA-N 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
- 125000005942 tetrahydropyridyl group Chemical group 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims 2
- AYUFHVKOYVDQHJ-UHFFFAOYSA-N 2-[3,5-bis(trifluoromethyl)phenyl]-2-methyl-n-[4-(2-methylphenyl)pyridin-3-yl]propanamide Chemical compound CC1=CC=CC=C1C1=CC=NC=C1NC(=O)C(C)(C)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 AYUFHVKOYVDQHJ-UHFFFAOYSA-N 0.000 claims 1
- FZXNGEHWLDLVOH-UHFFFAOYSA-N 2-[3,5-bis(trifluoromethyl)phenyl]-n-methyl-n-[4-(2-methylphenyl)pyridin-3-yl]acetamide Chemical compound C=1N=CC=C(C=2C(=CC=CC=2)C)C=1N(C)C(=O)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 FZXNGEHWLDLVOH-UHFFFAOYSA-N 0.000 claims 1
- QFIVBZWBVYGHFV-UHFFFAOYSA-N 4-(2-methylphenyl)pyridine-3-carboxamide Chemical compound CC1=CC=CC=C1C1=CC=NC=C1C(N)=O QFIVBZWBVYGHFV-UHFFFAOYSA-N 0.000 claims 1
- MEPYIKQCUYZUJC-UHFFFAOYSA-N n-[1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-n-methyl-4-(2-methylphenyl)pyridine-3-carboxamide Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1C(C)N(C)C(=O)C1=CN=CC=C1C1=CC=CC=C1C MEPYIKQCUYZUJC-UHFFFAOYSA-N 0.000 claims 1
- LENPPWYNSXXLIB-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-n-methyl-2-(2-methylphenyl)-4-(4-methylpiperazin-1-yl)benzamide Chemical compound C=1C=C(N2CCN(C)CC2)C=C(C=2C(=CC=CC=2)C)C=1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 LENPPWYNSXXLIB-UHFFFAOYSA-N 0.000 claims 1
- ZROIXVDZKWSSQO-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-n-methyl-4-phenylpyridine-3-carboxamide Chemical compound C=1N=CC=C(C=2C=CC=CC=2)C=1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 ZROIXVDZKWSSQO-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 131
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 123
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 93
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 74
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 65
- 239000000203 mixture Substances 0.000 description 58
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 54
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 48
- 239000011541 reaction mixture Substances 0.000 description 46
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- NSJVYHOPHZMZPN-UHFFFAOYSA-N (2-methylphenyl)boronic acid Chemical compound CC1=CC=CC=C1B(O)O NSJVYHOPHZMZPN-UHFFFAOYSA-N 0.000 description 20
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 13
- 239000012267 brine Substances 0.000 description 13
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 13
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- RRCMGJCFMJBHQC-UHFFFAOYSA-N (2-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1Cl RRCMGJCFMJBHQC-UHFFFAOYSA-N 0.000 description 11
- 229910052786 argon Inorganic materials 0.000 description 11
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Classifications
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07D213/82—Amides; Imides in position 3
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
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- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
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- Veterinary Medicine (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
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EP99103504 | 1999-02-24 | ||
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AU3979099A (en) * | 1998-05-11 | 1999-11-29 | Philadelphia Health & Education Corporation | (mct-1), a human oncogene |
TR200102490T2 (tr) | 1999-02-24 | 2001-12-21 | F.Hoffmann-La Roche Ag | Fenil ve piridinil türevleri |
US6291465B1 (en) * | 1999-03-09 | 2001-09-18 | Hoffmann-La Roche Inc. | Biphenyl derivatives |
DE60006340T2 (de) * | 1999-11-29 | 2004-09-09 | F. Hoffmann-La Roche Ag | 2-(3,5-Bis-trifluoromethyl-phenyl)-N-methyl-N-(6-morpholin-4-yl-4-o-tolyl-pyridin-3-yl)-isobutyramid |
US6303790B1 (en) * | 1999-11-29 | 2001-10-16 | Hoffman-La Roche Inc. | Process for the preparation of pyridine derivatives |
AUPQ514600A0 (en) | 2000-01-18 | 2000-02-10 | James Cook University | Brain injury treatment |
JP3938651B2 (ja) * | 2000-04-13 | 2007-06-27 | セントラル硝子株式会社 | 光学活性α−メチル−ビス−3、5−(トリフルオロメチル)ベンジルアミンの製造方法 |
RS50932B (sr) * | 2000-07-14 | 2010-08-31 | F. Hoffmann-La Roche Ag. | N-oksidi kao prolekovi 4-fenil-piridinskih derivata koji su antagonisti nk1 receptora |
TWI287003B (en) * | 2000-07-24 | 2007-09-21 | Hoffmann La Roche | 4-phenyl-pyridine derivatives |
TWI259180B (en) * | 2000-08-08 | 2006-08-01 | Hoffmann La Roche | 4-Phenyl-pyridine derivatives |
CA2431397C (fr) | 2000-12-14 | 2007-05-01 | F. Hoffmann-La Roche Ag | Matrice lipide auto-emulsifiante (selm) |
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