ZA200400492B - Novel compounds. - Google Patents
Novel compounds. Download PDFInfo
- Publication number
- ZA200400492B ZA200400492B ZA200400492A ZA200400492A ZA200400492B ZA 200400492 B ZA200400492 B ZA 200400492B ZA 200400492 A ZA200400492 A ZA 200400492A ZA 200400492 A ZA200400492 A ZA 200400492A ZA 200400492 B ZA200400492 B ZA 200400492B
- Authority
- ZA
- South Africa
- Prior art keywords
- aminocarbonyl
- amino
- thiophenecarboxamide
- phenyl
- carboxamide
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 111
- 238000000034 method Methods 0.000 claims abstract description 75
- 230000008569 process Effects 0.000 claims abstract description 15
- 238000002360 preparation method Methods 0.000 claims abstract description 13
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
- 238000002560 therapeutic procedure Methods 0.000 claims abstract description 7
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 232
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 115
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 85
- 125000000217 alkyl group Chemical group 0.000 claims description 50
- 150000003839 salts Chemical class 0.000 claims description 45
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 44
- 239000000203 mixture Substances 0.000 claims description 42
- -1 cyano, hydroxyl Chemical group 0.000 claims description 41
- YNSCKPCDFIDINW-UHFFFAOYSA-N 3-[[2-[[1-[2-(dimethylamino)acetyl]-6-methoxy-4,4-dimethyl-2,3-dihydroquinolin-7-yl]amino]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]thiophene-2-carboxamide Chemical compound COC1=CC(C(CCN2C(=O)CN(C)C)(C)C)=C2C=C1NC(N=C1NC=CC1=1)=NC=1NC=1C=CSC=1C(N)=O YNSCKPCDFIDINW-UHFFFAOYSA-N 0.000 claims description 40
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 38
- 201000010099 disease Diseases 0.000 claims description 33
- 125000003545 alkoxy group Chemical group 0.000 claims description 32
- 229910052736 halogen Inorganic materials 0.000 claims description 26
- 150000002367 halogens Chemical class 0.000 claims description 26
- 229910052760 oxygen Inorganic materials 0.000 claims description 26
- DAUYIKBTMNZABP-UHFFFAOYSA-N thiophene-3-carboxamide Chemical compound NC(=O)C=1C=CSC=1 DAUYIKBTMNZABP-UHFFFAOYSA-N 0.000 claims description 25
- 229920006395 saturated elastomer Polymers 0.000 claims description 24
- 229910052717 sulfur Inorganic materials 0.000 claims description 22
- 238000011282 treatment Methods 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 230000000694 effects Effects 0.000 claims description 16
- 238000011321 prophylaxis Methods 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 10
- 230000005764 inhibitory process Effects 0.000 claims description 10
- 206010028980 Neoplasm Diseases 0.000 claims description 9
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- 230000009286 beneficial effect Effects 0.000 claims description 7
- 150000003857 carboxamides Chemical class 0.000 claims description 7
- 208000027866 inflammatory disease Diseases 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 125000002950 monocyclic group Chemical group 0.000 claims description 7
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 7
- 201000011510 cancer Diseases 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 239000002671 adjuvant Substances 0.000 claims description 5
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 5
- 208000006673 asthma Diseases 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 208000035475 disorder Diseases 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 201000006417 multiple sclerosis Diseases 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 5
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims description 4
- 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 3
- 125000001589 carboacyl group Chemical group 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- CBEAESHJSAILDI-UHFFFAOYSA-N 2-(carbamoylamino)-5-(2-cyclopentyloxyphenyl)thiophene-3-carboxamide Chemical compound NC(=O)C1=C(NC(=O)N)SC(C=2C(=CC=CC=2)OC2CCCC2)=C1 CBEAESHJSAILDI-UHFFFAOYSA-N 0.000 claims description 2
- PIXFUHWDLQWBQS-UHFFFAOYSA-N 2-(carbamoylamino)-5-(2-pyrrolidin-3-yloxyphenyl)thiophene-3-carboxamide Chemical compound NC(=O)C1=C(NC(=O)N)SC(C=2C(=CC=CC=2)OC2CNCC2)=C1 PIXFUHWDLQWBQS-UHFFFAOYSA-N 0.000 claims description 2
- XVEAHPQPDVGWIP-UHFFFAOYSA-N 2-(carbamoylamino)-5-(4-pyrrolidin-1-ylphenyl)thiophene-3-carboxamide Chemical compound NC(=O)C1=C(NC(=O)N)SC(C=2C=CC(=CC=2)N2CCCC2)=C1 XVEAHPQPDVGWIP-UHFFFAOYSA-N 0.000 claims description 2
- VYDFXSFBPALUDR-UHFFFAOYSA-N 2-(carbamoylamino)-5-[2-(1-cyclopropylpyrrolidin-3-yl)oxyphenyl]thiophene-3-carboxamide Chemical compound NC(=O)C1=C(NC(=O)N)SC(C=2C(=CC=CC=2)OC2CN(CC2)C2CC2)=C1 VYDFXSFBPALUDR-UHFFFAOYSA-N 0.000 claims description 2
- ZEOCVQJWMJVRHY-UHFFFAOYSA-N 2-(carbamoylamino)-5-[2-(1-ethylpyrrolidin-3-yl)oxyphenyl]thiophene-3-carboxamide Chemical compound C1N(CC)CCC1OC1=CC=CC=C1C1=CC(C(N)=O)=C(NC(N)=O)S1 ZEOCVQJWMJVRHY-UHFFFAOYSA-N 0.000 claims description 2
- IQPABPZLFAGODU-UHFFFAOYSA-N 2-(carbamoylamino)-5-[2-(1-propan-2-ylpyrrolidin-3-yl)oxyphenyl]thiophene-3-carboxamide Chemical compound C1N(C(C)C)CCC1OC1=CC=CC=C1C1=CC(C(N)=O)=C(NC(N)=O)S1 IQPABPZLFAGODU-UHFFFAOYSA-N 0.000 claims description 2
- JYPJMVCYTQYTCQ-UHFFFAOYSA-N 2-(carbamoylamino)-5-[2-(2-hydroxyethoxy)phenyl]thiophene-3-carboxamide Chemical compound NC(=O)C1=C(NC(=O)N)SC(C=2C(=CC=CC=2)OCCO)=C1 JYPJMVCYTQYTCQ-UHFFFAOYSA-N 0.000 claims description 2
- RRYOCHACORNMMP-UHFFFAOYSA-N 2-(carbamoylamino)-5-[2-(2-phenylethoxy)phenyl]thiophene-3-carboxamide Chemical compound NC(=O)C1=C(NC(=O)N)SC(C=2C(=CC=CC=2)OCCC=2C=CC=CC=2)=C1 RRYOCHACORNMMP-UHFFFAOYSA-N 0.000 claims description 2
- SEKBXASOOSKNQD-UHFFFAOYSA-N 2-(carbamoylamino)-5-[2-(cyclopropylmethoxy)phenyl]thiophene-3-carboxamide Chemical compound NC(=O)C1=C(NC(=O)N)SC(C=2C(=CC=CC=2)OCC2CC2)=C1 SEKBXASOOSKNQD-UHFFFAOYSA-N 0.000 claims description 2
- SKUPKHUAMWCUSE-UHFFFAOYSA-N 2-(carbamoylamino)-5-[2-[(4-fluorophenyl)methoxy]phenyl]thiophene-3-carboxamide Chemical compound NC(=O)C1=C(NC(=O)N)SC(C=2C(=CC=CC=2)OCC=2C=CC(F)=CC=2)=C1 SKUPKHUAMWCUSE-UHFFFAOYSA-N 0.000 claims description 2
- QRCFTMKBDURRLX-UHFFFAOYSA-N 2-(carbamoylamino)-5-[2-[(4-propan-2-ylpiperazin-1-yl)methyl]phenyl]thiophene-3-carboxamide Chemical compound C1CN(C(C)C)CCN1CC1=CC=CC=C1C1=CC(C(N)=O)=C(NC(N)=O)S1 QRCFTMKBDURRLX-UHFFFAOYSA-N 0.000 claims description 2
- OFUFBUOIPOVSMK-UHFFFAOYSA-N 2-(carbamoylamino)-5-[2-[2-(4-hydroxypiperidin-1-yl)ethoxy]phenyl]thiophene-3-carboxamide Chemical compound NC(=O)C1=C(NC(=O)N)SC(C=2C(=CC=CC=2)OCCN2CCC(O)CC2)=C1 OFUFBUOIPOVSMK-UHFFFAOYSA-N 0.000 claims description 2
- KPPCPTVCZJDUSK-UHFFFAOYSA-N 2-(carbamoylamino)-5-[3-chloro-4-[2-(2-methoxyethoxy)ethoxy]phenyl]thiophene-3-carboxamide Chemical compound C1=C(Cl)C(OCCOCCOC)=CC=C1C1=CC(C(N)=O)=C(NC(N)=O)S1 KPPCPTVCZJDUSK-UHFFFAOYSA-N 0.000 claims description 2
- DXMIRHYMLCQWKL-UHFFFAOYSA-N 2-(carbamoylamino)-5-[3-fluoro-4-(morpholin-4-ylmethyl)phenyl]thiophene-3-carboxamide Chemical compound NC(=O)C1=C(NC(=O)N)SC(C=2C=C(F)C(CN3CCOCC3)=CC=2)=C1 DXMIRHYMLCQWKL-UHFFFAOYSA-N 0.000 claims description 2
- YPTZGJIPFJQFPF-UHFFFAOYSA-N 2-(carbamoylamino)-5-[4-(2-methylpropoxy)-3-(morpholin-4-ylmethyl)phenyl]thiophene-3-carboxamide Chemical compound CC(C)COC1=CC=C(C=2SC(NC(N)=O)=C(C(N)=O)C=2)C=C1CN1CCOCC1 YPTZGJIPFJQFPF-UHFFFAOYSA-N 0.000 claims description 2
- KHESYNPAOYKYSS-UHFFFAOYSA-N 2-(carbamoylamino)-5-[4-(morpholin-4-ylmethyl)phenyl]thiophene-3-carboxamide Chemical compound NC(=O)C1=C(NC(=O)N)SC(C=2C=CC(CN3CCOCC3)=CC=2)=C1 KHESYNPAOYKYSS-UHFFFAOYSA-N 0.000 claims description 2
- SNFACXIEVJUSMA-UHFFFAOYSA-N 2-(carbamoylamino)-5-[4-(pyrrolidin-1-ylmethyl)phenyl]thiophene-3-carboxamide Chemical compound NC(=O)C1=C(NC(=O)N)SC(C=2C=CC(CN3CCCC3)=CC=2)=C1 SNFACXIEVJUSMA-UHFFFAOYSA-N 0.000 claims description 2
- HSTMLKQZZRBSOQ-UHFFFAOYSA-N 2-(carbamoylamino)-5-[4-[2-(2-methoxyethoxy)ethoxy]phenyl]thiophene-3-carboxamide Chemical compound C1=CC(OCCOCCOC)=CC=C1C1=CC(C(N)=O)=C(NC(N)=O)S1 HSTMLKQZZRBSOQ-UHFFFAOYSA-N 0.000 claims description 2
- KNPVGHQASYMLOB-UHFFFAOYSA-N 2-(carbamoylamino)-5-[4-[2-(cyclopropylmethoxy)ethoxy]phenyl]thiophene-3-carboxamide Chemical compound NC(=O)C1=C(NC(=O)N)SC(C=2C=CC(OCCOCC3CC3)=CC=2)=C1 KNPVGHQASYMLOB-UHFFFAOYSA-N 0.000 claims description 2
- LCZPICZKTBKARQ-UHFFFAOYSA-N 2-(carbamoylamino)-5-[4-[[2-(2-hydroxyethyl)piperazin-1-yl]methyl]phenyl]thiophene-3-carboxamide Chemical compound NC(=O)C1=C(NC(=O)N)SC(C=2C=CC(CN3C(CNCC3)CCO)=CC=2)=C1 LCZPICZKTBKARQ-UHFFFAOYSA-N 0.000 claims description 2
- IRBJFKJHIZODKG-UHFFFAOYSA-N 2-(carbamoylamino)-5-[4-[[3-(hydroxymethyl)piperidin-1-yl]methyl]phenyl]thiophene-3-carboxamide Chemical compound NC(=O)C1=C(NC(=O)N)SC(C=2C=CC(CN3CC(CO)CCC3)=CC=2)=C1 IRBJFKJHIZODKG-UHFFFAOYSA-N 0.000 claims description 2
- BQZCIVRSKAGHDU-UHFFFAOYSA-N 2-(carbamoylamino)-5-[4-[[4-(hydroxymethyl)piperidin-1-yl]methyl]phenyl]thiophene-3-carboxamide Chemical compound NC(=O)C1=C(NC(=O)N)SC(C=2C=CC(CN3CCC(CO)CC3)=CC=2)=C1 BQZCIVRSKAGHDU-UHFFFAOYSA-N 0.000 claims description 2
- MULAGLGWNHRXCT-UHFFFAOYSA-N 2-(carbamoylamino)-5-[5-methoxy-2-(1-propan-2-ylpyrrolidin-3-yl)oxyphenyl]thiophene-3-carboxamide Chemical compound C=1C(C(N)=O)=C(NC(N)=O)SC=1C1=CC(OC)=CC=C1OC1CCN(C(C)C)C1 MULAGLGWNHRXCT-UHFFFAOYSA-N 0.000 claims description 2
- PYNVALHOZOCJTF-UHFFFAOYSA-N 2-(carbamoylamino)-5-[5-methyl-2-(1-propan-2-ylpyrrolidin-3-yl)oxyphenyl]thiophene-3-carboxamide Chemical compound C1N(C(C)C)CCC1OC1=CC=C(C)C=C1C1=CC(C(N)=O)=C(NC(N)=O)S1 PYNVALHOZOCJTF-UHFFFAOYSA-N 0.000 claims description 2
- MOWJKFWTFZWXHW-UHFFFAOYSA-N 3-(carbamoylamino)-5-[4-(morpholin-4-ylmethyl)phenyl]thiophene-2-carboxamide Chemical compound S1C(C(N)=O)=C(NC(=O)N)C=C1C(C=C1)=CC=C1CN1CCOCC1 MOWJKFWTFZWXHW-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000002540 isothiocyanates Chemical class 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 16
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 1
- BNTNDICFUPQAPZ-UHFFFAOYSA-N 2-(carbamoylamino)-5-(4-piperidin-1-ylphenyl)thiophene-3-carboxamide Chemical compound NC(=O)C1=C(NC(=O)N)SC(C=2C=CC(=CC=2)N2CCCCC2)=C1 BNTNDICFUPQAPZ-UHFFFAOYSA-N 0.000 claims 1
- VMZFSZDGXVHSSW-UHFFFAOYSA-N 2-(carbamoylamino)-5-(6-cyclopentyloxypyridin-3-yl)thiophene-3-carboxamide Chemical compound NC(=O)C1=C(NC(=O)N)SC(C=2C=NC(OC3CCCC3)=CC=2)=C1 VMZFSZDGXVHSSW-UHFFFAOYSA-N 0.000 claims 1
- UEDFPFOTZXXACH-UHFFFAOYSA-N 2-(carbamoylamino)-5-(6-pyrrolidin-1-ylpyridin-3-yl)thiophene-3-carboxamide Chemical compound NC(=O)C1=C(NC(=O)N)SC(C=2C=NC(=CC=2)N2CCCC2)=C1 UEDFPFOTZXXACH-UHFFFAOYSA-N 0.000 claims 1
- ZBZJVIVRHNWCRD-UHFFFAOYSA-N 2-(carbamoylamino)-5-[2-(1-methylpiperidin-4-yl)oxyphenyl]thiophene-3-carboxamide Chemical compound C1CN(C)CCC1OC1=CC=CC=C1C1=CC(C(N)=O)=C(NC(N)=O)S1 ZBZJVIVRHNWCRD-UHFFFAOYSA-N 0.000 claims 1
- KWWYGJABIBLKCA-UHFFFAOYSA-N 2-(carbamoylamino)-5-[2-(1-propan-2-ylpyrrolidin-3-yl)oxy-4-(trifluoromethyl)phenyl]thiophene-3-carboxamide Chemical compound C1N(C(C)C)CCC1OC1=CC(C(F)(F)F)=CC=C1C1=CC(C(N)=O)=C(NC(N)=O)S1 KWWYGJABIBLKCA-UHFFFAOYSA-N 0.000 claims 1
- LLWVGYGSWRIMMG-UHFFFAOYSA-N 2-(carbamoylamino)-5-[2-(1-propan-2-ylpyrrolidin-3-yl)oxy-5-(trifluoromethyl)phenyl]thiophene-3-carboxamide Chemical compound C1N(C(C)C)CCC1OC1=CC=C(C(F)(F)F)C=C1C1=CC(C(N)=O)=C(NC(N)=O)S1 LLWVGYGSWRIMMG-UHFFFAOYSA-N 0.000 claims 1
- XJUGDNZGIUWOBK-UHFFFAOYSA-N 2-(carbamoylamino)-5-[2-[(1-methylpiperidin-2-yl)methoxy]phenyl]thiophene-3-carboxamide Chemical compound CN1CCCCC1COC1=CC=CC=C1C1=CC(C(N)=O)=C(NC(N)=O)S1 XJUGDNZGIUWOBK-UHFFFAOYSA-N 0.000 claims 1
- DHRPDQLXZRVLMU-SECBINFHSA-N 2-(carbamoylamino)-5-[2-[(3r)-oxolan-3-yl]oxyphenyl]thiophene-3-carboxamide Chemical compound NC(=O)C1=C(NC(=O)N)SC(C=2C(=CC=CC=2)O[C@H]2COCC2)=C1 DHRPDQLXZRVLMU-SECBINFHSA-N 0.000 claims 1
- MOGNRBKWUKUDRJ-UHFFFAOYSA-N 2-(carbamoylamino)-5-[2-[2-(3,3-difluoropyrrolidin-1-yl)ethoxy]phenyl]thiophene-3-carboxamide Chemical compound NC(=O)C1=C(NC(=O)N)SC(C=2C(=CC=CC=2)OCCN2CC(F)(F)CC2)=C1 MOGNRBKWUKUDRJ-UHFFFAOYSA-N 0.000 claims 1
- WUYBXCMCUDHGBR-UHFFFAOYSA-N 2-(carbamoylamino)-5-[3,5-difluoro-2-(1-propan-2-ylpyrrolidin-3-yl)oxyphenyl]thiophene-3-carboxamide Chemical compound C1N(C(C)C)CCC1OC1=C(F)C=C(F)C=C1C1=CC(C(N)=O)=C(NC(N)=O)S1 WUYBXCMCUDHGBR-UHFFFAOYSA-N 0.000 claims 1
- XAPNPQAMUNEMBB-UHFFFAOYSA-N 2-(carbamoylamino)-5-[3-(1,3-thiazol-4-ylmethoxy)phenyl]thiophene-3-carboxamide Chemical compound NC(=O)C1=C(NC(=O)N)SC(C=2C=C(OCC=3N=CSC=3)C=CC=2)=C1 XAPNPQAMUNEMBB-UHFFFAOYSA-N 0.000 claims 1
- GBGDOWRNVDCFMD-UHFFFAOYSA-N 2-(carbamoylamino)-5-[3-(morpholin-4-ylmethyl)phenyl]thiophene-3-carboxamide Chemical compound NC(=O)C1=C(NC(=O)N)SC(C=2C=C(CN3CCOCC3)C=CC=2)=C1 GBGDOWRNVDCFMD-UHFFFAOYSA-N 0.000 claims 1
- FYMYPRLQJWPQCS-UHFFFAOYSA-N 2-(carbamoylamino)-5-[3-chloro-4-(oxolan-2-ylmethoxy)phenyl]thiophene-3-carboxamide Chemical compound NC(=O)C1=C(NC(=O)N)SC(C=2C=C(Cl)C(OCC3OCCC3)=CC=2)=C1 FYMYPRLQJWPQCS-UHFFFAOYSA-N 0.000 claims 1
- OWYCEQHCDQLKGK-UHFFFAOYSA-N 2-(carbamoylamino)-5-[3-methoxy-2-(1-propan-2-ylpyrrolidin-3-yl)oxyphenyl]thiophene-3-carboxamide Chemical compound C1CN(C(C)C)CC1OC=1C(OC)=CC=CC=1C1=CC(C(N)=O)=C(NC(N)=O)S1 OWYCEQHCDQLKGK-UHFFFAOYSA-N 0.000 claims 1
- SXGKBUNDGMXGAP-UHFFFAOYSA-N 2-(carbamoylamino)-5-[4,5-difluoro-2-(1-propan-2-ylpyrrolidin-3-yl)oxyphenyl]thiophene-3-carboxamide Chemical compound C1N(C(C)C)CCC1OC1=CC(F)=C(F)C=C1C1=CC(C(N)=O)=C(NC(N)=O)S1 SXGKBUNDGMXGAP-UHFFFAOYSA-N 0.000 claims 1
- BCQUFEGOZCRRIM-UHFFFAOYSA-N 2-(carbamoylamino)-5-[4-(1,4-oxazepan-4-ylmethyl)phenyl]thiophene-3-carboxamide Chemical compound NC(=O)C1=C(NC(=O)N)SC(C=2C=CC(CN3CCOCCC3)=CC=2)=C1 BCQUFEGOZCRRIM-UHFFFAOYSA-N 0.000 claims 1
- NGMBUJUMFVAGMT-UHFFFAOYSA-N 2-(carbamoylamino)-5-[4-(2-methoxyethoxy)-2-(2-piperidin-1-ylethoxy)phenyl]thiophene-3-carboxamide Chemical compound C1CCCCN1CCOC1=CC(OCCOC)=CC=C1C1=CC(C(N)=O)=C(NC(N)=O)S1 NGMBUJUMFVAGMT-UHFFFAOYSA-N 0.000 claims 1
- VQVSLYYUZICPND-UHFFFAOYSA-N 2-(carbamoylamino)-5-[4-(8-oxa-3-azabicyclo[3.2.1]octan-3-ylmethyl)phenyl]thiophene-3-carboxamide Chemical compound NC(=O)C1=C(NC(=O)N)SC(C=2C=CC(CN3CC4CCC(O4)C3)=CC=2)=C1 VQVSLYYUZICPND-UHFFFAOYSA-N 0.000 claims 1
- YAOTUNPGXRJLCJ-UHFFFAOYSA-N 2-(carbamoylamino)-5-[4-(morpholin-4-ylmethyl)-2-(2-piperidin-1-ylethoxy)phenyl]thiophene-3-carboxamide Chemical compound NC(=O)C1=C(NC(=O)N)SC(C=2C(=CC(CN3CCOCC3)=CC=2)OCCN2CCCCC2)=C1 YAOTUNPGXRJLCJ-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur 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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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms 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
- C07D413/04—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 directly linked by a ring-member-to-ring-member bond
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- C07—ORGANIC CHEMISTRY
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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
- 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
- C07D413/10—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 carbon chain containing aromatic rings
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- 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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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
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- Bioinformatics & Cheminformatics (AREA)
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- Rheumatology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Use Of Switch Circuits For Exchanges And Methods Of Control Of Multiplex Exchanges (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
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SE0102616A SE0102616D0 (sv) | 2001-07-25 | 2001-07-25 | Novel compounds |
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ZA200400492B true ZA200400492B (en) | 2005-04-22 |
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ZA200400492A ZA200400492B (en) | 2001-07-25 | 2004-01-22 | Novel compounds. |
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US (3) | US7125896B2 (zh) |
EP (1) | EP1421074B1 (zh) |
JP (1) | JP4571800B2 (zh) |
KR (1) | KR100931172B1 (zh) |
CN (1) | CN1263751C (zh) |
AT (1) | ATE482944T1 (zh) |
AU (1) | AU2002355245B2 (zh) |
BR (1) | BR0211473A (zh) |
CA (1) | CA2454703C (zh) |
CY (1) | CY1111543T1 (zh) |
DE (1) | DE60237828D1 (zh) |
DK (1) | DK1421074T3 (zh) |
ES (1) | ES2351436T3 (zh) |
HK (1) | HK1071129A1 (zh) |
IL (2) | IL160028A0 (zh) |
MX (1) | MXPA04000756A (zh) |
NO (1) | NO326684B1 (zh) |
NZ (1) | NZ530750A (zh) |
PT (1) | PT1421074E (zh) |
SE (1) | SE0102616D0 (zh) |
WO (1) | WO2003010158A1 (zh) |
ZA (1) | ZA200400492B (zh) |
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JP2005509645A (ja) * | 2001-10-30 | 2005-04-14 | ファルマシア・コーポレーション | 炎症処置用のヘテロ芳香族カルボキサミド誘導体 |
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AU2003270701B2 (en) | 2002-10-31 | 2009-11-12 | Amgen Inc. | Antiinflammation agents |
WO2004053087A2 (en) * | 2002-12-06 | 2004-06-24 | Smithkline Beecham Corporation | Nf-κb inhibitors |
ES2345438T3 (es) | 2002-12-10 | 2010-09-23 | Virochem Pharma Inc. | Compuestos y metodos para el tratamiento o prevencion de infecciones por flavivirus. |
SE0300092D0 (sv) | 2003-01-15 | 2003-01-15 | Astrazeneca Ab | Novel compounds |
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JP4735261B2 (ja) * | 2003-06-27 | 2011-07-27 | Msd株式会社 | ヘテロアリールオキシ含窒素飽和ヘテロ環誘導体 |
EP1660474B1 (en) * | 2003-08-15 | 2008-10-29 | AstraZeneca AB | Substituted thiophenes and uses thereof |
JP2007516270A (ja) * | 2003-12-23 | 2007-06-21 | ソマンタ リミテッド | 抗ガン性化合物としてのアントラキノン化合物 |
GB0403744D0 (en) * | 2004-02-20 | 2004-03-24 | Astrazeneca Ab | Chemical process |
WO2005105777A1 (en) * | 2004-05-05 | 2005-11-10 | Pharmacia & Upjohn Company Llc | Substituted thiophene amide compounds for the treatment of inflammation |
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BRPI0611674A2 (pt) | 2005-06-30 | 2009-04-28 | Smithkline Beecham Corp | compostos quÍmicos |
US8063071B2 (en) | 2007-10-31 | 2011-11-22 | GlaxoSmithKline, LLC | Chemical compounds |
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-
2001
- 2001-07-25 SE SE0102616A patent/SE0102616D0/xx unknown
-
2002
- 2002-07-19 BR BR0211473-9A patent/BR0211473A/pt not_active Application Discontinuation
- 2002-07-19 PT PT02751935T patent/PT1421074E/pt unknown
- 2002-07-19 AT AT02751935T patent/ATE482944T1/de active
- 2002-07-19 CA CA2454703A patent/CA2454703C/en not_active Expired - Fee Related
- 2002-07-19 MX MXPA04000756A patent/MXPA04000756A/es active IP Right Grant
- 2002-07-19 KR KR1020047001154A patent/KR100931172B1/ko not_active IP Right Cessation
- 2002-07-19 US US10/484,569 patent/US7125896B2/en not_active Expired - Fee Related
- 2002-07-19 NZ NZ530750A patent/NZ530750A/en not_active IP Right Cessation
- 2002-07-19 DK DK02751935.4T patent/DK1421074T3/da active
- 2002-07-19 JP JP2003515517A patent/JP4571800B2/ja not_active Expired - Fee Related
- 2002-07-19 IL IL16002802A patent/IL160028A0/xx unknown
- 2002-07-19 ES ES02751935T patent/ES2351436T3/es not_active Expired - Lifetime
- 2002-07-19 CN CNB028158369A patent/CN1263751C/zh not_active Expired - Fee Related
- 2002-07-19 DE DE60237828T patent/DE60237828D1/de not_active Expired - Lifetime
- 2002-07-19 WO PCT/SE2002/001403 patent/WO2003010158A1/en active IP Right Grant
- 2002-07-19 AU AU2002355245A patent/AU2002355245B2/en not_active Ceased
- 2002-07-19 EP EP02751935A patent/EP1421074B1/en not_active Expired - Lifetime
-
2004
- 2004-01-22 IL IL160028A patent/IL160028A/en not_active IP Right Cessation
- 2004-01-22 ZA ZA200400492A patent/ZA200400492B/en unknown
- 2004-01-23 NO NO20040313A patent/NO326684B1/no not_active IP Right Cessation
-
2005
- 2005-04-27 HK HK05103629A patent/HK1071129A1/xx not_active IP Right Cessation
-
2006
- 2006-09-06 US US11/516,225 patent/US7956084B2/en not_active Expired - Fee Related
-
2010
- 2010-11-25 CY CY20101101069T patent/CY1111543T1/el unknown
- 2010-12-23 US US12/977,640 patent/US20110152234A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
JP2005503372A (ja) | 2005-02-03 |
IL160028A0 (en) | 2004-06-20 |
SE0102616D0 (sv) | 2001-07-25 |
ES2351436T3 (es) | 2011-02-04 |
ATE482944T1 (de) | 2010-10-15 |
CA2454703C (en) | 2011-01-04 |
IL160028A (en) | 2012-01-31 |
CN1541214A (zh) | 2004-10-27 |
DK1421074T3 (da) | 2010-12-13 |
MXPA04000756A (es) | 2004-04-20 |
US20070015819A1 (en) | 2007-01-18 |
US7125896B2 (en) | 2006-10-24 |
US7956084B2 (en) | 2011-06-07 |
NZ530750A (en) | 2005-08-26 |
JP4571800B2 (ja) | 2010-10-27 |
KR20040018520A (ko) | 2004-03-03 |
CA2454703A1 (en) | 2003-02-06 |
KR100931172B1 (ko) | 2009-12-11 |
HK1071129A1 (en) | 2005-07-08 |
DE60237828D1 (de) | 2010-11-11 |
WO2003010158A1 (en) | 2003-02-06 |
BR0211473A (pt) | 2004-10-26 |
US20040242573A1 (en) | 2004-12-02 |
EP1421074A1 (en) | 2004-05-26 |
AU2002355245B2 (en) | 2008-05-15 |
CY1111543T1 (el) | 2015-08-05 |
NO20040313L (no) | 2004-03-25 |
CN1263751C (zh) | 2006-07-12 |
NO326684B1 (no) | 2009-01-26 |
US20110152234A1 (en) | 2011-06-23 |
EP1421074B1 (en) | 2010-09-29 |
PT1421074E (pt) | 2010-11-29 |
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