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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| US8106091B2 (en) | 2006-11-01 | 2012-01-31 | Chroma Therapeutics Ltd. | Inhibitors of IKK-beta serine-threonine protein kinase |
| CA2668338A1 (en) * | 2006-11-01 | 2008-05-08 | Chroma Therapeutics Ltd. | Ikk-.beta. serine-threonine protein kinase inhibitors |
| CA2670260A1 (en) | 2006-11-15 | 2008-05-22 | Virochem Pharma Inc. | Thiophene analogues for the treatment or prevention of flavivirus infections |
| KR20090109551A (ko) * | 2007-01-15 | 2009-10-20 | 산텐 세이야꾸 가부시키가이샤 | ＩκＢ 키나아제 β 저해 활성을 갖는 신규 인돌 유도체 |
| PE20081889A1 (es) | 2007-03-23 | 2009-03-05 | Smithkline Beecham Corp | Indol carboxamidas como inhibidores de ikk2 |
| EA201001708A1 (ru) * | 2008-04-26 | 2011-06-30 | Хрома Терапьютикс Лтд. | Замещённые тиофенкарбоксамиды их применение в качестве ингибиторов ikk-бета серин-треонин протеинкиназ |
| US8344144B2 (en) * | 2008-06-18 | 2013-01-01 | Merck Sharp & Dohme Corp. | Inhibitors of Janus kinases |
| CN102089281A (zh) * | 2008-07-14 | 2011-06-08 | 参天制药株式会社 | 具有氨基甲酰基、脲基及取代氧基的新型吲哚衍生物 |
| CN102171204B (zh) | 2008-10-02 | 2014-08-20 | 旭化成制药株式会社 | 8位取代异喹啉衍生物及其用途 |
| WO2010102968A1 (en) | 2009-03-10 | 2010-09-16 | Glaxo Group Limited | Indole derivatives as ikk2 inhibitors |
| BRPI1013328A2 (pt) * | 2009-04-16 | 2016-03-29 | Telik Inc | 4-amino-benzoil-2-(fenilamino) tiofeno-3-carbonitrilas substituídas e 4-a-mino-5benzoil-2-(fenilamino) tiofeno-3-carboxamidas substituídas como inibidores da polimerização de tubulina |
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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 |
| WO2012046793A1 (ja) * | 2010-10-07 | 2012-04-12 | 参天製薬株式会社 | ウレイド基とアミノカルボニル基を置換基として有するチオフェン誘導体を有効成分として含有する新規ｊａｋ３阻害剤 |
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| GB201021992D0 (en) | 2010-12-23 | 2011-02-02 | Astrazeneca Ab | Compound |
| KR20250028525A (ko) * | 2012-03-14 | 2025-02-28 | 머크 샤프 앤드 돔 엘엘씨 | Cgrp 수용체 길항제의 제조 방법 |
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| AU2014240042C1 (en) | 2013-03-14 | 2019-09-05 | Celltaxis, Llc | Inhibitors of leukotriene A4 hydrolase |
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-
2001
- 2001-07-25 SE SE0102616A patent/SE0102616D0/xx unknown
-
2002
- 2002-07-19 AT AT02751935T patent/ATE482944T1/de active
- 2002-07-19 PT PT02751935T patent/PT1421074E/pt unknown
- 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 MX MXPA04000756A patent/MXPA04000756A/es active IP Right Grant
- 2002-07-19 CA CA2454703A patent/CA2454703C/en not_active Expired - Fee Related
- 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 AU AU2002355245A patent/AU2002355245B2/en not_active Ceased
- 2002-07-19 KR KR1020047001154A patent/KR100931172B1/ko not_active Expired - Fee Related
- 2002-07-19 BR BR0211473-9A patent/BR0211473A/pt not_active Application Discontinuation
- 2002-07-19 DK DK02751935.4T patent/DK1421074T3/da active
- 2002-07-19 EP EP02751935A patent/EP1421074B1/en not_active Expired - Lifetime
- 2002-07-19 IL IL16002802A patent/IL160028A0/xx unknown
- 2002-07-19 JP JP2003515517A patent/JP4571800B2/ja not_active Expired - Fee Related
- 2002-07-19 WO PCT/SE2002/001403 patent/WO2003010158A1/en not_active Ceased
- 2002-07-19 DE DE60237828T patent/DE60237828D1/de 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
-
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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