JP2005503372A5 - - Google Patents
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- Publication number
- JP2005503372A5 JP2005503372A5 JP2003515517A JP2003515517A JP2005503372A5 JP 2005503372 A5 JP2005503372 A5 JP 2005503372A5 JP 2003515517 A JP2003515517 A JP 2003515517A JP 2003515517 A JP2003515517 A JP 2003515517A JP 2005503372 A5 JP2005503372 A5 JP 2005503372A5
- Authority
- JP
- Japan
- Prior art keywords
- aminocarbonyl
- amino
- thiophenecarboxamide
- phenyl
- carboxamide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- DETHMLJGORXQMH-UHFFFAOYSA-N 2-(carbamoylamino)-5-[6-(2,2-difluoroethoxy)pyridin-3-yl]thiophene-3-carboxamide Chemical compound NC(=O)C1=C(NC(=O)N)SC(C=2C=NC(OCC(F)F)=CC=2)=C1 DETHMLJGORXQMH-UHFFFAOYSA-N 0.000 claims description 2
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 94
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 42
- -1 cyano, hydroxyl Chemical group 0.000 claims 24
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 13
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 229910052760 oxygen Inorganic materials 0.000 claims 10
- 229910052717 sulfur Inorganic materials 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 8
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 230000003287 optical effect Effects 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- DAUYIKBTMNZABP-UHFFFAOYSA-N thiophene-3-carboxamide Chemical compound NC(=O)C=1C=CSC=1 DAUYIKBTMNZABP-UHFFFAOYSA-N 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- XXNFYPXWIKQOHJ-UHFFFAOYSA-N 1-[[4-[4-carbamoyl-5-(carbamoylamino)thiophen-2-yl]phenyl]methyl]-n,n-diethylpiperidine-3-carboxamide Chemical compound C1C(C(=O)N(CC)CC)CCCN1CC1=CC=C(C=2SC(NC(N)=O)=C(C(N)=O)C=2)C=C1 XXNFYPXWIKQOHJ-UHFFFAOYSA-N 0.000 claims 1
- MLWUARYPQLXDJI-UHFFFAOYSA-N 2-(carbamoylamino)-4-methyl-5-[4-(1,2,5-thiadiazol-3-ylmethoxy)phenyl]thiophene-3-carboxamide Chemical compound S1C(NC(N)=O)=C(C(N)=O)C(C)=C1C(C=C1)=CC=C1OCC1=NSN=C1 MLWUARYPQLXDJI-UHFFFAOYSA-N 0.000 claims 1
- PXSULNGOEYZRES-UHFFFAOYSA-N 2-(carbamoylamino)-4-methyl-5-[4-(1,3-thiazol-4-ylmethoxy)phenyl]thiophene-3-carboxamide Chemical compound S1C(NC(N)=O)=C(C(N)=O)C(C)=C1C(C=C1)=CC=C1OCC1=CSC=N1 PXSULNGOEYZRES-UHFFFAOYSA-N 0.000 claims 1
- BNFBZBWZJIFILL-UHFFFAOYSA-N 2-(carbamoylamino)-4-methyl-5-[4-(1-methylazepan-3-yl)oxyphenyl]thiophene-3-carboxamide Chemical compound C1N(C)CCCCC1OC1=CC=C(C2=C(C(C(N)=O)=C(NC(N)=O)S2)C)C=C1 BNFBZBWZJIFILL-UHFFFAOYSA-N 0.000 claims 1
- QTCKLYYOFQZOQY-UHFFFAOYSA-N 2-(carbamoylamino)-4-methyl-5-[4-[2-(2,2,6,6-tetramethylpiperidin-1-yl)ethoxy]phenyl]thiophene-3-carboxamide Chemical compound S1C(NC(N)=O)=C(C(N)=O)C(C)=C1C(C=C1)=CC=C1OCCN1C(C)(C)CCCC1(C)C QTCKLYYOFQZOQY-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- NINYIKFHJMWTJX-UHFFFAOYSA-N 2-(carbamoylamino)-5-(2-phenylmethoxyphenyl)thiophene-3-carboxamide Chemical compound NC(=O)C1=C(NC(=O)N)SC(C=2C(=CC=CC=2)OCC=2C=CC=CC=2)=C1 NINYIKFHJMWTJX-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- GLPRRTOTBSXXJH-UHFFFAOYSA-N 2-(carbamoylamino)-5-(4-imidazol-1-ylphenyl)thiophene-3-carboxamide Chemical compound NC(=O)C1=C(NC(=O)N)SC(C=2C=CC(=CC=2)N2C=NC=C2)=C1 GLPRRTOTBSXXJH-UHFFFAOYSA-N 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
- 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 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
- FNDHNBZREMFSRK-UHFFFAOYSA-N 2-(carbamoylamino)-5-(6-piperidin-1-ylpyridin-3-yl)thiophene-3-carboxamide Chemical compound NC(=O)C1=C(NC(=O)N)SC(C=2C=NC(=CC=2)N2CCCCC2)=C1 FNDHNBZREMFSRK-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
- 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 1
- 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 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
- WEGAEHTWVKXAQG-UHFFFAOYSA-N 2-(carbamoylamino)-5-[2-(1-methylpyrrolidin-3-yl)oxyphenyl]thiophene-3-carboxamide Chemical compound C1N(C)CCC1OC1=CC=CC=C1C1=CC(C(N)=O)=C(NC(N)=O)S1 WEGAEHTWVKXAQG-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
- 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 1
- 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 1
- 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 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
- DHRPDQLXZRVLMU-VIFPVBQESA-N 2-(carbamoylamino)-5-[2-[(3s)-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-VIFPVBQESA-N 0.000 claims 1
- 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 1
- QPJOHBXEAPLRHA-UHFFFAOYSA-N 2-(carbamoylamino)-5-[2-[(4-methylpiperazin-1-yl)methyl]phenyl]thiophene-3-carboxamide Chemical compound C1CN(C)CCN1CC1=CC=CC=C1C1=CC(C(N)=O)=C(NC(N)=O)S1 QPJOHBXEAPLRHA-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- BRNZAKQKEABRDF-UHFFFAOYSA-N 2-(carbamoylamino)-5-[2-[1-(2-methoxyethyl)pyrrolidin-3-yl]oxyphenyl]thiophene-3-carboxamide Chemical compound C1N(CCOC)CCC1OC1=CC=CC=C1C1=CC(C(N)=O)=C(NC(N)=O)S1 BRNZAKQKEABRDF-UHFFFAOYSA-N 0.000 claims 1
- IXCPSOPKAAALSH-UHFFFAOYSA-N 2-(carbamoylamino)-5-[2-[2-(2,2,6,6-tetramethylpiperidin-1-yl)ethoxy]phenyl]thiophene-3-carboxamide Chemical compound CC1(C)CCCC(C)(C)N1CCOC1=CC=CC=C1C1=CC(C(N)=O)=C(NC(N)=O)S1 IXCPSOPKAAALSH-UHFFFAOYSA-N 0.000 claims 1
- BYEJGDPZLQQXRO-UHFFFAOYSA-N 2-(carbamoylamino)-5-[2-[2-(2,2,6-trimethylpiperidin-1-yl)ethoxy]phenyl]thiophene-3-carboxamide Chemical compound CC1CCCC(C)(C)N1CCOC1=CC=CC=C1C1=CC(C(N)=O)=C(NC(N)=O)S1 BYEJGDPZLQQXRO-UHFFFAOYSA-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
- NYBPSXGKXWNGAO-UHFFFAOYSA-N 2-(carbamoylamino)-5-[2-[2-(4,4-difluoropiperidin-1-yl)ethoxy]phenyl]thiophene-3-carboxamide Chemical compound NC(=O)C1=C(NC(=O)N)SC(C=2C(=CC=CC=2)OCCN2CCC(F)(F)CC2)=C1 NYBPSXGKXWNGAO-UHFFFAOYSA-N 0.000 claims 1
- WBTNOSBQTUHKAN-UHFFFAOYSA-N 2-(carbamoylamino)-5-[2-[2-(4-chlorophenyl)ethoxy]phenyl]thiophene-3-carboxamide Chemical compound NC(=O)C1=C(NC(=O)N)SC(C=2C(=CC=CC=2)OCCC=2C=CC(Cl)=CC=2)=C1 WBTNOSBQTUHKAN-UHFFFAOYSA-N 0.000 claims 1
- HRFMVWFSYJKFPZ-UHFFFAOYSA-N 2-(carbamoylamino)-5-[2-[2-(4-fluorophenyl)ethoxy]phenyl]thiophene-3-carboxamide Chemical compound NC(=O)C1=C(NC(=O)N)SC(C=2C(=CC=CC=2)OCCC=2C=CC(F)=CC=2)=C1 HRFMVWFSYJKFPZ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- JOHZVKWQRFMJSG-LLVKDONJSA-N 2-(carbamoylamino)-5-[2-[[(2r)-1-methylpyrrolidin-2-yl]methoxy]phenyl]thiophene-3-carboxamide Chemical compound CN1CCC[C@@H]1COC1=CC=CC=C1C1=CC(C(N)=O)=C(NC(N)=O)S1 JOHZVKWQRFMJSG-LLVKDONJSA-N 0.000 claims 1
- JOHZVKWQRFMJSG-NSHDSACASA-N 2-(carbamoylamino)-5-[2-[[(2s)-1-methylpyrrolidin-2-yl]methoxy]phenyl]thiophene-3-carboxamide Chemical compound CN1CCC[C@H]1COC1=CC=CC=C1C1=CC(C(N)=O)=C(NC(N)=O)S1 JOHZVKWQRFMJSG-NSHDSACASA-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
- IOEYZXFYZJUDDD-UHFFFAOYSA-N 2-(carbamoylamino)-5-[3-(morpholin-4-ylmethyl)-2-(1-propan-2-ylpyrrolidin-3-yl)oxyphenyl]thiophene-3-carboxamide Chemical compound C1N(C(C)C)CCC1OC(C(=CC=C1)C=2SC(NC(N)=O)=C(C(N)=O)C=2)=C1CN1CCOCC1 IOEYZXFYZJUDDD-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
- 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 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
- UQXDOVBNWLUIAF-UHFFFAOYSA-N 2-(carbamoylamino)-5-[4-(1,3-thiazol-4-ylmethoxy)phenyl]thiophene-3-carboxamide Chemical compound NC(=O)C1=C(NC(=O)N)SC(C=2C=CC(OCC=3N=CSC=3)=CC=2)=C1 UQXDOVBNWLUIAF-UHFFFAOYSA-N 0.000 claims 1
- MPOLORMCGARKBS-UHFFFAOYSA-N 2-(carbamoylamino)-5-[4-(2-morpholin-4-ylacetyl)phenyl]thiophene-3-carboxamide Chemical compound NC(=O)C1=C(NC(=O)N)SC(C=2C=CC(=CC=2)C(=O)CN2CCOCC2)=C1 MPOLORMCGARKBS-UHFFFAOYSA-N 0.000 claims 1
- SVVXYACPSGOLNH-UHFFFAOYSA-N 2-(carbamoylamino)-5-[4-(cyclopropylmethoxy)phenyl]thiophene-3-carboxamide Chemical compound NC(=O)C1=C(NC(=O)N)SC(C=2C=CC(OCC3CC3)=CC=2)=C1 SVVXYACPSGOLNH-UHFFFAOYSA-N 0.000 claims 1
- CYGKPEKPWARPDK-UHFFFAOYSA-N 2-(carbamoylamino)-5-[4-(oxolan-2-ylmethoxy)phenyl]thiophene-3-carboxamide Chemical compound NC(=O)C1=C(NC(=O)N)SC(C=2C=CC(OCC3OCCC3)=CC=2)=C1 CYGKPEKPWARPDK-UHFFFAOYSA-N 0.000 claims 1
- AXCZKDDKOUPJJV-UHFFFAOYSA-N 2-(carbamoylamino)-5-[4-[(3,5-dimethyl-1,2-oxazol-4-yl)methoxy]phenyl]-4-methylthiophene-3-carboxamide Chemical compound CC1=NOC(C)=C1COC1=CC=C(C2=C(C(C(N)=O)=C(NC(N)=O)S2)C)C=C1 AXCZKDDKOUPJJV-UHFFFAOYSA-N 0.000 claims 1
- JWLSCCSLFHOSIJ-UHFFFAOYSA-N 2-(carbamoylamino)-5-[4-[(3-hydroxypyrrolidin-1-yl)methyl]phenyl]thiophene-3-carboxamide Chemical compound NC(=O)C1=C(NC(=O)N)SC(C=2C=CC(CN3CC(O)CC3)=CC=2)=C1 JWLSCCSLFHOSIJ-UHFFFAOYSA-N 0.000 claims 1
- VJCWAYSOZQEWJM-UHFFFAOYSA-N 2-(carbamoylamino)-5-[4-[(4-chlorophenyl)methoxy]phenyl]-4-methylthiophene-3-carboxamide Chemical compound S1C(NC(N)=O)=C(C(N)=O)C(C)=C1C(C=C1)=CC=C1OCC1=CC=C(Cl)C=C1 VJCWAYSOZQEWJM-UHFFFAOYSA-N 0.000 claims 1
- XWCZJSAIVDCFTQ-UHFFFAOYSA-N 2-(carbamoylamino)-5-[4-[(5-chlorothiophen-2-yl)methoxy]phenyl]-4-methylthiophene-3-carboxamide Chemical compound S1C(NC(N)=O)=C(C(N)=O)C(C)=C1C(C=C1)=CC=C1OCC1=CC=C(Cl)S1 XWCZJSAIVDCFTQ-UHFFFAOYSA-N 0.000 claims 1
- STGHZEGJPQXHSD-UHFFFAOYSA-N 2-(carbamoylamino)-5-[4-[2-(2-methoxyethoxy)ethoxy]-3-methylphenyl]thiophene-3-carboxamide Chemical compound C1=C(C)C(OCCOCCOC)=CC=C1C1=CC(C(N)=O)=C(NC(N)=O)S1 STGHZEGJPQXHSD-UHFFFAOYSA-N 0.000 claims 1
- 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 1
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| CN100413861C (zh) | 2002-12-10 | 2008-08-27 | 维勒凯姆制药股份有限公司 | 用于治疗或预防黄病毒感染的化合物 |
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| DE602006003661D1 (de) | 2005-06-06 | 2008-12-24 | Lilly Co Eli | Ampa-rezeptoren-verstärker |
| DE102005029382B3 (de) * | 2005-06-24 | 2006-12-21 | Sanofi-Aventis Deutschland Gmbh | Alkoxymethylyl-substituierte Benzoesäurederivate, Verfahren zu ihrer Herstellung und ihre Anwendung als Arzneimittel |
| MX2007016541A (es) | 2005-06-30 | 2008-03-07 | Smithkline Beecham Corp | Compuestos quimicos. |
| US8063071B2 (en) | 2007-10-31 | 2011-11-22 | GlaxoSmithKline, LLC | Chemical compounds |
| US20100069387A1 (en) * | 2005-09-07 | 2010-03-18 | Palmer Stephen S | IKK Inhibitors for the Treatment of Endometriosis |
| EP1976828B1 (en) | 2005-12-29 | 2016-12-21 | Celtaxsys, Inc. | Diamine derivatives as inhibitors of leukotriene a4 hydrolase |
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| US8003695B2 (en) | 2006-11-01 | 2011-08-23 | Chroma Therapeutics Ltd. | IKK-beta serine-threonine protein kinase inhibitors |
| ATE524454T1 (de) | 2006-11-01 | 2011-09-15 | Chroma Therapeutics Ltd | Inhibitoren von ikk-beta serinthreoninproteinkinase |
| PT2104674E (pt) | 2006-11-15 | 2013-07-26 | Virochem Pharma Inc | Análogos de tiofeno para o tratamento ou prevenção de infeções por flavivírus |
| US8193237B2 (en) * | 2007-01-15 | 2012-06-05 | Santen Pharmaceutical Co., Ltd. | Indole derivative having IκB kinase β inhibitory activity |
| PE20081889A1 (es) | 2007-03-23 | 2009-03-05 | Smithkline Beecham Corp | Indol carboxamidas como inhibidores de ikk2 |
| US20110046210A1 (en) * | 2008-04-26 | 2011-02-24 | Chroma Therapeutics Ltd. | Substituted thiopenecarboxamides as ikk-beta serine-, threonine-protein kinase inhibitors |
| EP2299816B1 (en) * | 2008-06-18 | 2013-11-13 | Merck Sharp & Dohme Corp. | Inhibitors of janus kinases |
| JP2010043070A (ja) * | 2008-07-14 | 2010-02-25 | Santen Pharmaceut Co Ltd | カルバモイル基、ウレイド基及び置換オキシ基を有する新規インドール誘導体 |
| PL2366699T3 (pl) | 2008-10-02 | 2013-12-31 | Asahi Kasei Pharma Corp | 8-podstawiona pochodna izochinoliny i jej zastosowanie |
| WO2010102968A1 (en) | 2009-03-10 | 2010-09-16 | Glaxo Group Limited | Indole derivatives as ikk2 inhibitors |
| KR20120006543A (ko) * | 2009-04-16 | 2012-01-18 | 텔리크 인코포레이티드 | 튜불린 중합 저해제로서 치환된 4-아미노-5-벤조일-2-(페닐아미노)티오펜-3-카르보니트릴및 치환된 4-아미노-5-벤조일-2-(페닐아미노)티오펜-3-카르복스아미드 |
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| CN101812007B (zh) * | 2010-04-27 | 2011-11-23 | 浙江大学 | 氨基吡咯类化合物及其制备方法 |
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-
2001
- 2001-07-25 SE SE0102616A patent/SE0102616D0/xx unknown
-
2002
- 2002-07-19 US US10/484,569 patent/US7125896B2/en not_active Expired - Fee Related
- 2002-07-19 DE DE60237828T patent/DE60237828D1/de not_active Expired - Lifetime
- 2002-07-19 CA CA2454703A patent/CA2454703C/en not_active Expired - Fee Related
- 2002-07-19 DK DK02751935.4T patent/DK1421074T3/da active
- 2002-07-19 PT PT02751935T patent/PT1421074E/pt unknown
- 2002-07-19 EP EP02751935A patent/EP1421074B1/en not_active Expired - Lifetime
- 2002-07-19 CN CNB028158369A patent/CN1263751C/zh not_active Expired - Fee Related
- 2002-07-19 WO PCT/SE2002/001403 patent/WO2003010158A1/en not_active Ceased
- 2002-07-19 IL IL16002802A patent/IL160028A0/xx unknown
- 2002-07-19 AU AU2002355245A patent/AU2002355245B2/en not_active Ceased
- 2002-07-19 ES ES02751935T patent/ES2351436T3/es not_active Expired - Lifetime
- 2002-07-19 AT AT02751935T patent/ATE482944T1/de active
- 2002-07-19 JP JP2003515517A patent/JP4571800B2/ja not_active Expired - Fee Related
- 2002-07-19 KR KR1020047001154A patent/KR100931172B1/ko not_active Expired - Fee Related
- 2002-07-19 MX MXPA04000756A patent/MXPA04000756A/es active IP Right Grant
- 2002-07-19 BR BR0211473-9A patent/BR0211473A/pt not_active Application Discontinuation
- 2002-07-19 NZ NZ530750A patent/NZ530750A/en not_active IP Right Cessation
-
2004
- 2004-01-22 ZA ZA200400492A patent/ZA200400492B/en unknown
- 2004-01-22 IL IL160028A patent/IL160028A/en not_active IP Right Cessation
- 2004-01-23 NO NO20040313A patent/NO326684B1/no 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
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