NO320289B1 - Amidderivater, fremgangsmate for fremstilling og anvendelse derav, samt farmasoytisk preparat. - Google Patents
Amidderivater, fremgangsmate for fremstilling og anvendelse derav, samt farmasoytisk preparat. Download PDFInfo
- Publication number
- NO320289B1 NO320289B1 NO20010534A NO20010534A NO320289B1 NO 320289 B1 NO320289 B1 NO 320289B1 NO 20010534 A NO20010534 A NO 20010534A NO 20010534 A NO20010534 A NO 20010534A NO 320289 B1 NO320289 B1 NO 320289B1
- Authority
- NO
- Norway
- Prior art keywords
- alkyl
- alkylamino
- amino
- alkoxy
- carboxamide
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 56
- 150000001408 amides Chemical class 0.000 title claims description 26
- 238000002360 preparation method Methods 0.000 title claims description 13
- 230000008569 process Effects 0.000 title claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- -1 cyano, mercapto, nitro, amino, carboxy, carbamoyl Chemical group 0.000 claims description 286
- 125000000217 alkyl group Chemical group 0.000 claims description 194
- 125000003282 alkyl amino group Chemical group 0.000 claims description 164
- 150000001875 compounds Chemical class 0.000 claims description 112
- 125000003545 alkoxy group Chemical group 0.000 claims description 81
- 125000001424 substituent group Chemical group 0.000 claims description 66
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 53
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 34
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 102000004127 Cytokines Human genes 0.000 claims description 20
- 108090000695 Cytokines Proteins 0.000 claims description 20
- 150000002148 esters Chemical class 0.000 claims description 20
- 125000000623 heterocyclic group Chemical group 0.000 claims description 20
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 17
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 16
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 125000006239 protecting group Chemical group 0.000 claims description 15
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 14
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 14
- 239000000460 chlorine Substances 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 239000011570 nicotinamide Substances 0.000 claims description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- 235000005152 nicotinamide Nutrition 0.000 claims description 11
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 9
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 8
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
- 125000001589 carboacyl group Chemical group 0.000 claims description 8
- 238000011282 treatment Methods 0.000 claims description 8
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 claims description 7
- 125000004947 alkyl aryl amino group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000005239 aroylamino group Chemical group 0.000 claims description 6
- 125000001769 aryl amino group Chemical group 0.000 claims description 6
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 6
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 6
- 125000005224 heteroarylcarbonylamino group Chemical group 0.000 claims description 6
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 6
- 125000005419 heteroarylsulfonylamino group Chemical group 0.000 claims description 6
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 6
- 238000001727 in vivo Methods 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 6
- 230000029936 alkylation Effects 0.000 claims description 5
- 238000005804 alkylation reaction Methods 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000006264 diethylaminomethyl group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 125000006534 ethyl amino methyl group Chemical group [H]N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000000524 functional group Chemical group 0.000 claims description 4
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 4
- 125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000005493 quinolyl group Chemical group 0.000 claims description 4
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 230000010933 acylation Effects 0.000 claims description 3
- 238000005917 acylation reaction Methods 0.000 claims description 3
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 3
- 238000003776 cleavage reaction Methods 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 3
- 125000003635 2-dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 2
- QHSQGUIARYBWFN-UHFFFAOYSA-N 6-[(2-amino-2-methylpropyl)amino]-n-[2-methyl-5-[(2-morpholin-4-ylpyridine-4-carbonyl)amino]phenyl]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2C=NC(NCC(C)(C)N)=CC=2)C(C)=CC=C1NC(=O)C(C=1)=CC=NC=1N1CCOCC1 QHSQGUIARYBWFN-UHFFFAOYSA-N 0.000 claims description 2
- HLOFQXUITYKUJV-UHFFFAOYSA-N 6-[2-(diethylamino)ethylamino]-n-[2-methyl-5-[(2-morpholin-4-ylpyridine-4-carbonyl)amino]phenyl]pyridine-3-carboxamide Chemical compound C1=NC(NCCN(CC)CC)=CC=C1C(=O)NC1=CC(NC(=O)C=2C=C(N=CC=2)N2CCOCC2)=CC=C1C HLOFQXUITYKUJV-UHFFFAOYSA-N 0.000 claims description 2
- KWKZMJHJCALSSV-UHFFFAOYSA-N 6-[3-(dimethylamino)propylamino]-n-[2-methyl-5-[(2-morpholin-4-ylpyridine-4-carbonyl)amino]phenyl]pyridine-3-carboxamide Chemical compound C1=NC(NCCCN(C)C)=CC=C1C(=O)NC1=CC(NC(=O)C=2C=C(N=CC=2)N2CCOCC2)=CC=C1C KWKZMJHJCALSSV-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004601 benzofurazanyl group Chemical group N1=C2C(=NO1)C(=CC=C2)* 0.000 claims description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- CLIDMUTWHLMPMN-UHFFFAOYSA-N imidazole-1-carboxamide Chemical compound NC(=O)N1C=CN=C1 CLIDMUTWHLMPMN-UHFFFAOYSA-N 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 2
- 230000001404 mediated effect Effects 0.000 claims description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
- SHLWKXMWBBNABL-UHFFFAOYSA-N n-[2-methyl-5-[(2-morpholin-4-ylpyridine-4-carbonyl)amino]phenyl]-6-(3-morpholin-4-ylpropylamino)pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2C=NC(NCCCN3CCOCC3)=CC=2)C(C)=CC=C1NC(=O)C(C=1)=CC=NC=1N1CCOCC1 SHLWKXMWBBNABL-UHFFFAOYSA-N 0.000 claims description 2
- DVPVWRYIDHDOOO-UHFFFAOYSA-N n-[2-methyl-5-[(2-morpholin-4-ylpyridine-4-carbonyl)amino]phenyl]-6-[2-(1-methylpyrrolidin-2-yl)ethylamino]pyridine-3-carboxamide Chemical compound CN1CCCC1CCNC1=CC=C(C(=O)NC=2C(=CC=C(NC(=O)C=3C=C(N=CC=3)N3CCOCC3)C=2)C)C=N1 DVPVWRYIDHDOOO-UHFFFAOYSA-N 0.000 claims description 2
- UJIIUIYOOLZLGN-UHFFFAOYSA-N n-[4-chloro-3-[[2-(4-methylpiperazin-1-yl)pyridine-4-carbonyl]amino]phenyl]-2-morpholin-4-ylpyridine-4-carboxamide Chemical compound C1CN(C)CCN1C1=CC(C(=O)NC=2C(=CC=C(NC(=O)C=3C=C(N=CC=3)N3CCOCC3)C=2)Cl)=CC=N1 UJIIUIYOOLZLGN-UHFFFAOYSA-N 0.000 claims description 2
- ZDSHLEPLXDTPEX-UHFFFAOYSA-N n-[4-chloro-3-[[2-[4-(2-hydroxyethyl)piperazin-1-yl]pyridine-4-carbonyl]amino]phenyl]-2-morpholin-4-ylpyridine-4-carboxamide Chemical compound C1CN(CCO)CCN1C1=CC(C(=O)NC=2C(=CC=C(NC(=O)C=3C=C(N=CC=3)N3CCOCC3)C=2)Cl)=CC=N1 ZDSHLEPLXDTPEX-UHFFFAOYSA-N 0.000 claims description 2
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- LDNSHTVNGGHGQJ-UHFFFAOYSA-N pyrrole-1-carboxamide Chemical compound NC(=O)N1C=CC=C1 LDNSHTVNGGHGQJ-UHFFFAOYSA-N 0.000 claims description 2
- 230000007017 scission Effects 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- UZFKIHMFDWGBKC-UHFFFAOYSA-N pyridine-4-carboxamide Chemical compound NC(=O)C1=CC=NC=C1.NC(=O)C1=CC=NC=C1 UZFKIHMFDWGBKC-UHFFFAOYSA-N 0.000 claims 2
- 150000003857 carboxamides Chemical class 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- NXMUXNBTBBSCFQ-UHFFFAOYSA-N n-[5-[(3-fluoro-5-morpholin-4-ylbenzoyl)amino]-2-methylphenyl]-6-(4-methylpiperazin-1-yl)pyridine-3-carboxamide Chemical compound C1CN(C)CCN1C1=CC=C(C(=O)NC=2C(=CC=C(NC(=O)C=3C=C(C=C(F)C=3)N3CCOCC3)C=2)C)C=N1 NXMUXNBTBBSCFQ-UHFFFAOYSA-N 0.000 claims 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 126
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 101
- 238000001819 mass spectrum Methods 0.000 description 90
- 239000000203 mixture Substances 0.000 description 87
- 239000000047 product Substances 0.000 description 72
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 57
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- 239000007787 solid Substances 0.000 description 46
- 239000000243 solution Substances 0.000 description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
- 239000000376 reactant Substances 0.000 description 40
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 34
- 239000007858 starting material Substances 0.000 description 27
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 26
- 239000011541 reaction mixture Substances 0.000 description 26
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- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
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- 229920006395 saturated elastomer Polymers 0.000 description 20
- 238000012360 testing method Methods 0.000 description 20
- UONRWDXHIHSMET-UHFFFAOYSA-N 6-chloro-n-[2-methyl-5-[(2-morpholin-4-ylpyridine-4-carbonyl)amino]phenyl]pyridine-3-carboxamide Chemical compound C1=C(NC(=O)C=2C=NC(Cl)=CC=2)C(C)=CC=C1NC(=O)C(C=1)=CC=NC=1N1CCOCC1 UONRWDXHIHSMET-UHFFFAOYSA-N 0.000 description 19
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- 241000282414 Homo sapiens Species 0.000 description 17
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 17
- 235000017557 sodium bicarbonate Nutrition 0.000 description 17
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
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- 239000000706 filtrate Substances 0.000 description 9
- ZHZZJUVVTWHONI-UHFFFAOYSA-N n-(3-amino-4-methylphenyl)-3-(dimethylamino)benzamide Chemical compound CN(C)C1=CC=CC(C(=O)NC=2C=C(N)C(C)=CC=2)=C1 ZHZZJUVVTWHONI-UHFFFAOYSA-N 0.000 description 9
- 210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 9
- FMEBIWNKYZUWFV-UHFFFAOYSA-N 6-chloropyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)N=C1 FMEBIWNKYZUWFV-UHFFFAOYSA-N 0.000 description 8
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- 239000003112 inhibitor Substances 0.000 description 8
- VFQXVTODMYMSMJ-UHFFFAOYSA-N isonicotinamide Chemical compound NC(=O)C1=CC=NC=C1 VFQXVTODMYMSMJ-UHFFFAOYSA-N 0.000 description 8
- STWNGMSGPBZFMX-UHFFFAOYSA-N pyridine-3-carboxamide Chemical compound NC(=O)C1=CC=CN=C1.NC(=O)C1=CC=CN=C1 STWNGMSGPBZFMX-UHFFFAOYSA-N 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- GDIIPKWHAQGCJF-UHFFFAOYSA-N 4-Amino-2-nitrotoluene Chemical compound CC1=CC=C(N)C=C1[N+]([O-])=O GDIIPKWHAQGCJF-UHFFFAOYSA-N 0.000 description 7
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- 235000019341 magnesium sulphate Nutrition 0.000 description 7
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Classifications
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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
- C07D213/24—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 with substituted hydrocarbon radicals attached to ring carbon atoms
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- C07D213/00—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
- 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
- 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
- C07D213/60—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 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- C—CHEMISTRY; METALLURGY
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- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines 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 carbon atoms of the hetero ring
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- C—CHEMISTRY; METALLURGY
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- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more 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
- C07D261/18—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen
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- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
-
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- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D401/02—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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D401/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Chemical & Material Sciences (AREA)
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- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Cardiology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Heart & Thoracic Surgery (AREA)
- Dermatology (AREA)
- Endocrinology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pain & Pain Management (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Quinoline Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
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Applications Claiming Priority (3)
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GBGB9816838.8A GB9816838D0 (en) | 1998-08-04 | 1998-08-04 | Amide derivatives |
GBGB9824939.4A GB9824939D0 (en) | 1998-11-13 | 1998-11-13 | Amide derivatives |
PCT/GB1999/002489 WO2000007991A1 (en) | 1998-08-04 | 1999-07-29 | Amide derivatives useful as inhibitors of the production of cytokines |
Publications (3)
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NO20010534D0 NO20010534D0 (no) | 2001-01-31 |
NO20010534L NO20010534L (no) | 2001-03-15 |
NO320289B1 true NO320289B1 (no) | 2005-11-21 |
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NO20010534A NO320289B1 (no) | 1998-08-04 | 2001-01-31 | Amidderivater, fremgangsmate for fremstilling og anvendelse derav, samt farmasoytisk preparat. |
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US (2) | US6432949B1 (ja) |
EP (1) | EP1102750A1 (ja) |
JP (1) | JP2002522421A (ja) |
KR (1) | KR20010099609A (ja) |
CN (1) | CN1142912C (ja) |
AU (1) | AU753741B2 (ja) |
BR (1) | BR9912729A (ja) |
CA (1) | CA2338121A1 (ja) |
HU (1) | HUP0103019A3 (ja) |
ID (1) | ID27652A (ja) |
IL (2) | IL141183A0 (ja) |
MX (1) | MXPA01000895A (ja) |
NO (1) | NO320289B1 (ja) |
NZ (1) | NZ509318A (ja) |
PL (1) | PL345817A1 (ja) |
RU (1) | RU2216541C2 (ja) |
SK (1) | SK1762001A3 (ja) |
TR (1) | TR200100300T2 (ja) |
WO (1) | WO2000007991A1 (ja) |
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GB9816837D0 (en) | 1998-08-04 | 1998-09-30 | Zeneca Ltd | Amide derivatives |
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PT1077930E (pt) | 1998-05-15 | 2005-03-31 | Astrazeneca Ab | Derivados de benzamida para o tratamento de doencas mediadas por citocinas |
SK286123B6 (sk) | 1998-05-15 | 2008-04-07 | Astrazeneca Ab | Benzamidové deriváty, spôsob ich prípravy, farmaceutická kompozícia a ich použitie na prípravu liečiva na liečenie chorôb sprostredkovaných cytokínmi |
JP2002522421A (ja) | 1998-08-04 | 2002-07-23 | アストラゼネカ アクチボラグ | サイトカイン産生の阻害剤として有用なアミド誘導体 |
EP1112070B1 (en) * | 1998-08-20 | 2004-05-12 | Smithkline Beecham Corporation | Novel substituted triazole compounds |
ID28267A (id) | 1998-09-25 | 2001-05-10 | Astrazeneca Ab | Turunan benzamida dan penggunaannya sebagai inhibitor sitokina |
BR0009083B1 (pt) * | 1999-03-17 | 2011-11-01 | derivado de amida compreendendo um núcleo de quinazolinona, processo para a preparação de um derivado de amida, composição farmacêutica, e, uso de um derivado de amida. | |
JP2002539187A (ja) | 1999-03-17 | 2002-11-19 | アストラゼネカ アクチボラグ | アミド誘導体 |
GB9906566D0 (en) | 1999-03-23 | 1999-05-19 | Zeneca Ltd | Chemical compounds |
GB9924092D0 (en) | 1999-10-13 | 1999-12-15 | Zeneca Ltd | Pyrimidine derivatives |
US6759410B1 (en) * | 1999-11-23 | 2004-07-06 | Smithline Beecham Corporation | 3,4-dihydro-(1H)-quinazolin-2-ones and their use as CSBP/p38 kinase inhibitors |
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US7323455B2 (en) * | 2004-03-24 | 2008-01-29 | Wyeth | 7-aryl 1,5-dihydro-4,1-benzoxazepin-2(3H)-one derivatives and their use as progesterone receptor modulators |
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WO2006106711A1 (ja) | 2005-03-30 | 2006-10-12 | Eisai R & D Management Co., Ltd. | ピリジン誘導体を含有する抗真菌剤 |
DE102005036763B4 (de) * | 2005-08-04 | 2007-07-26 | Inheco Industrial Heating And Cooling Gmbh | System aus mehreren Inkubatoren |
US7754717B2 (en) * | 2005-08-15 | 2010-07-13 | Amgen Inc. | Bis-aryl amide compounds and methods of use |
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GB9623833D0 (en) | 1996-11-16 | 1997-01-08 | Zeneca Ltd | Chemical compound |
WO1999015164A1 (en) | 1997-09-23 | 1999-04-01 | Zeneca Limited | Amide derivatives for the treatment of diseases mediated by cytokines |
GB9809347D0 (en) | 1998-05-05 | 1998-07-01 | Reckitt & Colmann Prod Ltd | Compositions |
PT1077930E (pt) | 1998-05-15 | 2005-03-31 | Astrazeneca Ab | Derivados de benzamida para o tratamento de doencas mediadas por citocinas |
SK286123B6 (sk) | 1998-05-15 | 2008-04-07 | Astrazeneca Ab | Benzamidové deriváty, spôsob ich prípravy, farmaceutická kompozícia a ich použitie na prípravu liečiva na liečenie chorôb sprostredkovaných cytokínmi |
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ID28267A (id) | 1998-09-25 | 2001-05-10 | Astrazeneca Ab | Turunan benzamida dan penggunaannya sebagai inhibitor sitokina |
EP1117653B1 (en) | 1998-10-01 | 2003-02-05 | AstraZeneca AB | Quinoline and quinazoline derivatives and their use as inhibitors of cytokine mediated diseases |
JP2002539187A (ja) | 1999-03-17 | 2002-11-19 | アストラゼネカ アクチボラグ | アミド誘導体 |
BR0009083B1 (pt) | 1999-03-17 | 2011-11-01 | derivado de amida compreendendo um núcleo de quinazolinona, processo para a preparação de um derivado de amida, composição farmacêutica, e, uso de um derivado de amida. | |
GB9906566D0 (en) | 1999-03-23 | 1999-05-19 | Zeneca Ltd | Chemical compounds |
GB9924092D0 (en) | 1999-10-13 | 1999-12-15 | Zeneca Ltd | Pyrimidine derivatives |
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- 1999-07-29 PL PL99345817A patent/PL345817A1/xx not_active Application Discontinuation
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- 1999-07-29 CN CNB998117234A patent/CN1142912C/zh not_active Expired - Fee Related
- 1999-07-29 AU AU51788/99A patent/AU753741B2/en not_active Ceased
- 1999-07-29 EP EP99936810A patent/EP1102750A1/en not_active Withdrawn
- 1999-07-29 WO PCT/GB1999/002489 patent/WO2000007991A1/en not_active Application Discontinuation
- 1999-07-29 ID IDW20010255A patent/ID27652A/id unknown
- 1999-07-29 IL IL14118399A patent/IL141183A0/xx not_active IP Right Cessation
- 1999-07-29 SK SK176-2001A patent/SK1762001A3/sk unknown
- 1999-07-29 CA CA002338121A patent/CA2338121A1/en not_active Abandoned
- 1999-07-29 TR TR2001/00300T patent/TR200100300T2/xx unknown
- 1999-07-29 HU HU0103019A patent/HUP0103019A3/hu unknown
- 1999-07-29 BR BR9912729-6A patent/BR9912729A/pt not_active IP Right Cessation
- 1999-07-29 MX MXPA01000895A patent/MXPA01000895A/es not_active IP Right Cessation
-
2001
- 2001-01-30 IL IL141183A patent/IL141183A/en unknown
- 2001-01-31 NO NO20010534A patent/NO320289B1/no unknown
-
2002
- 2002-07-11 US US10/192,495 patent/US7060700B2/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
US7060700B2 (en) | 2006-06-13 |
JP2002522421A (ja) | 2002-07-23 |
CA2338121A1 (en) | 2000-02-17 |
HUP0103019A2 (hu) | 2001-12-28 |
SK1762001A3 (en) | 2001-07-10 |
US6432949B1 (en) | 2002-08-13 |
EP1102750A1 (en) | 2001-05-30 |
NO20010534D0 (no) | 2001-01-31 |
AU5178899A (en) | 2000-02-28 |
CN1142912C (zh) | 2004-03-24 |
KR20010099609A (ko) | 2001-11-09 |
PL345817A1 (en) | 2002-01-14 |
TR200100300T2 (tr) | 2001-07-23 |
MXPA01000895A (es) | 2002-08-20 |
WO2000007991A1 (en) | 2000-02-17 |
CN1321150A (zh) | 2001-11-07 |
NZ509318A (en) | 2002-10-25 |
RU2216541C2 (ru) | 2003-11-20 |
AU753741B2 (en) | 2002-10-24 |
HUP0103019A3 (en) | 2002-01-28 |
US20030105142A1 (en) | 2003-06-05 |
BR9912729A (pt) | 2001-05-02 |
IL141183A0 (en) | 2002-02-10 |
ID27652A (id) | 2001-04-19 |
NO20010534L (no) | 2001-03-15 |
IL141183A (en) | 2006-10-31 |
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