JP2005503372A5 - - Google Patents
Download PDFInfo
- 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
Links
- 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
- DZNBDJNHHBMSNF-UHFFFAOYSA-N 2-(carbamoylamino)-5-[4-fluoro-2-(1-propan-2-ylpyrrolidin-3-yl)oxyphenyl]thiophene-3-carboxamide Chemical compound C1N(C(C)C)CCC1OC1=CC(F)=CC=C1C1=CC(C(N)=O)=C(NC(N)=O)S1 DZNBDJNHHBMSNF-UHFFFAOYSA-N 0.000 claims 1
- WEHJYNMGLXPJFX-UHFFFAOYSA-N 2-(carbamoylamino)-5-[4-methoxy-2-(1-propan-2-ylpyrrolidin-3-yl)oxyphenyl]thiophene-3-carboxamide Chemical compound C1CN(C(C)C)CC1OC1=CC(OC)=CC=C1C1=CC(C(N)=O)=C(NC(N)=O)S1 WEHJYNMGLXPJFX-UHFFFAOYSA-N 0.000 claims 1
- YLMAXHULIWOFRO-UHFFFAOYSA-N 2-(carbamoylamino)-5-[5-chloro-2-(1-propan-2-ylpyrrolidin-3-yl)oxyphenyl]thiophene-3-carboxamide Chemical compound C1N(C(C)C)CCC1OC1=CC=C(Cl)C=C1C1=CC(C(N)=O)=C(NC(N)=O)S1 YLMAXHULIWOFRO-UHFFFAOYSA-N 0.000 claims 1
- YVEXNRIZTICFCC-UHFFFAOYSA-N 2-(carbamoylamino)-5-[5-cyano-2-(1-propan-2-ylpyrrolidin-3-yl)oxyphenyl]thiophene-3-carboxamide Chemical compound C1N(C(C)C)CCC1OC1=CC=C(C#N)C=C1C1=CC(C(N)=O)=C(NC(N)=O)S1 YVEXNRIZTICFCC-UHFFFAOYSA-N 0.000 claims 1
- XYXJEUWKNSAAAK-UHFFFAOYSA-N 2-(carbamoylamino)-5-[5-fluoro-2-(1-propan-2-ylpyrrolidin-3-yl)oxyphenyl]thiophene-3-carboxamide Chemical compound C1N(C(C)C)CCC1OC1=CC=C(F)C=C1C1=CC(C(N)=O)=C(NC(N)=O)S1 XYXJEUWKNSAAAK-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- SMKKWMYIIDXOHH-UHFFFAOYSA-N 2-(carbamoylamino)-5-[6-(2,2-dimethyl-3-pyrrolidin-1-ylpropoxy)pyridin-3-yl]thiophene-3-carboxamide Chemical compound C1CCCN1CC(C)(C)COC(N=C1)=CC=C1C1=CC(C(N)=O)=C(NC(N)=O)S1 SMKKWMYIIDXOHH-UHFFFAOYSA-N 0.000 claims 1
- WALRXGVEOVSQHW-UHFFFAOYSA-N 2-(carbamoylamino)-5-[6-(4-ethylsulfonylpiperazin-1-yl)pyridin-3-yl]thiophene-3-carboxamide Chemical compound C1CN(S(=O)(=O)CC)CCN1C1=CC=C(C=2SC(NC(N)=O)=C(C(N)=O)C=2)C=N1 WALRXGVEOVSQHW-UHFFFAOYSA-N 0.000 claims 1
- NLUIHUAPDKBSGQ-UHFFFAOYSA-N 2-(carbamoylamino)-5-[6-(oxolan-2-ylmethoxy)pyridin-3-yl]thiophene-3-carboxamide Chemical compound NC(=O)C1=C(NC(=O)N)SC(C=2C=NC(OCC3OCCC3)=CC=2)=C1 NLUIHUAPDKBSGQ-UHFFFAOYSA-N 0.000 claims 1
- SIKFMTMLWLYUCM-UHFFFAOYSA-N 2-(carbamoylamino)-5-[6-[(1-methyl-5-oxopyrrolidin-3-yl)methoxy]pyridin-3-yl]thiophene-3-carboxamide Chemical compound C1C(=O)N(C)CC1COC1=CC=C(C=2SC(NC(N)=O)=C(C(N)=O)C=2)C=N1 SIKFMTMLWLYUCM-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 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 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 239000012948 isocyanate Substances 0.000 claims 1
- 150000002513 isocyanates Chemical class 0.000 claims 1
- 150000002540 isothiocyanates Chemical class 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- RJKKXWNULZCFGW-UHFFFAOYSA-N tert-butyl 3-[2-[4-carbamoyl-5-(carbamoylamino)thiophen-2-yl]phenoxy]pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC1OC1=CC=CC=C1C1=CC(C(N)=O)=C(NC(N)=O)S1 RJKKXWNULZCFGW-UHFFFAOYSA-N 0.000 claims 1
- DLJDWKTXEBVCGT-UHFFFAOYSA-N tert-butyl 4-[[2-[4-carbamoyl-5-(carbamoylamino)thiophen-2-yl]phenyl]methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1CC1=CC=CC=C1C1=CC(C(N)=O)=C(NC(N)=O)S1 DLJDWKTXEBVCGT-UHFFFAOYSA-N 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002158 endotoxin Substances 0.000 description 3
- 229920006008 lipopolysaccharide Polymers 0.000 description 3
- 210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- XSHZGHVZPLZCIL-UHFFFAOYSA-N 5-bromo-2-(2,2-difluoroethoxy)pyridine Chemical compound FC(F)COC1=CC=C(Br)C=N1 XSHZGHVZPLZCIL-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- ZHXUWDPHUQHFOV-UHFFFAOYSA-N 2,5-dibromopyridine Chemical compound BrC1=CC=C(Br)N=C1 ZHXUWDPHUQHFOV-UHFFFAOYSA-N 0.000 description 1
- HEUIRIDPRMRRIB-UHFFFAOYSA-N 5-bromo-2-(carbamoylamino)thiophene-3-carboxamide Chemical compound NC(=O)NC=1SC(Br)=CC=1C(N)=O HEUIRIDPRMRRIB-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 101000979342 Homo sapiens Nuclear factor NF-kappa-B p105 subunit Proteins 0.000 description 1
- 108010057466 NF-kappa B Proteins 0.000 description 1
- 102000003945 NF-kappa B Human genes 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 102100023050 Nuclear factor NF-kappa-B p105 subunit Human genes 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 1
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 1
- PZDZHSVBBNQZGU-UHFFFAOYSA-N [Ar].CCO Chemical compound [Ar].CCO PZDZHSVBBNQZGU-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
- 230000006433 tumor necrosis factor production Effects 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0102616A SE0102616D0 (sv) | 2001-07-25 | 2001-07-25 | Novel compounds |
| PCT/SE2002/001403 WO2003010158A1 (en) | 2001-07-25 | 2002-07-19 | Novel compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005503372A JP2005503372A (ja) | 2005-02-03 |
| JP2005503372A5 true JP2005503372A5 (enExample) | 2009-11-05 |
| JP4571800B2 JP4571800B2 (ja) | 2010-10-27 |
Family
ID=20284944
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003515517A Expired - Fee Related JP4571800B2 (ja) | 2001-07-25 | 2002-07-19 | 新規化合物 |
Country Status (21)
| Country | Link |
|---|---|
| US (3) | US7125896B2 (enExample) |
| EP (1) | EP1421074B1 (enExample) |
| JP (1) | JP4571800B2 (enExample) |
| KR (1) | KR100931172B1 (enExample) |
| CN (1) | CN1263751C (enExample) |
| AT (1) | ATE482944T1 (enExample) |
| AU (1) | AU2002355245B2 (enExample) |
| BR (1) | BR0211473A (enExample) |
| CA (1) | CA2454703C (enExample) |
| CY (1) | CY1111543T1 (enExample) |
| DE (1) | DE60237828D1 (enExample) |
| DK (1) | DK1421074T3 (enExample) |
| ES (1) | ES2351436T3 (enExample) |
| IL (2) | IL160028A0 (enExample) |
| MX (1) | MXPA04000756A (enExample) |
| NO (1) | NO326684B1 (enExample) |
| NZ (1) | NZ530750A (enExample) |
| PT (1) | PT1421074E (enExample) |
| SE (1) | SE0102616D0 (enExample) |
| WO (1) | WO2003010158A1 (enExample) |
| ZA (1) | ZA200400492B (enExample) |
Families Citing this family (58)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0003154D0 (en) * | 2000-02-12 | 2000-04-05 | Astrazeneca Uk Ltd | Novel compounds |
| EP2363396A1 (en) * | 2001-06-11 | 2011-09-07 | Virochem Pharma Inc. | Thiophene derivatives as antiviral agents for flavivirus infection |
| US8329924B2 (en) * | 2001-06-11 | 2012-12-11 | Vertex Pharmaceuticals (Canada) Incorporated | Compounds and methods for the treatment or prevention of Flavivirus infections |
| SE0102616D0 (sv) * | 2001-07-25 | 2001-07-25 | Astrazeneca Ab | Novel compounds |
| AU2002356871A1 (en) * | 2001-10-30 | 2003-05-12 | Pharmacia Corporation | Heteroaromatic carboxamide derivatives for the treatment of inflammation |
| US7375131B2 (en) | 2002-06-06 | 2008-05-20 | Smithklinebeecham Corp. | NF-κB inhibitors |
| EP1556053A4 (en) | 2002-10-31 | 2006-04-19 | Amgen Inc | ANTI-INFLAMMATORY AGENTS |
| WO2004053087A2 (en) * | 2002-12-06 | 2004-06-24 | Smithkline Beecham Corporation | Nf-κb inhibitors |
| DE60332482D1 (de) | 2002-12-10 | 2010-06-17 | Virochem Pharma Inc | Verbindungen und methoden zum behandeln oder vorbeugen von flavivirus infektionen |
| SE0300091D0 (sv) * | 2003-01-15 | 2003-01-15 | Astrazeneca Ab | Novel compounds |
| SE0300092D0 (sv) * | 2003-01-15 | 2003-01-15 | Astrazeneca Ab | Novel compounds |
| US7595316B2 (en) * | 2003-06-27 | 2009-09-29 | Banyu Pharmaceutical Co., Ltd. | Heteroaryloxy nitrogenous saturated heterocyclic derivative |
| ES2314443T3 (es) * | 2003-08-15 | 2009-03-16 | Astrazeneca Ab | Tiofenos sustituidos y sus usos. |
| EP1701939B1 (en) * | 2003-12-23 | 2009-02-25 | Somanta Limited | Anthraquinone compounds as anti cancer compounds |
| 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 |
| TW200616967A (en) | 2004-06-24 | 2006-06-01 | Smithkline Beecham Corp | Novel indazole carboxamides and their use |
| TW200626142A (en) | 2004-09-21 | 2006-08-01 | Glaxo Group Ltd | Chemical compounds |
| 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 |
| NZ563687A (en) | 2005-06-30 | 2011-07-29 | Smithkline Beecham Corp | 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-[2-(1-methylethyl)-2,3-dihydro-1H-isoindol-5-yl]-1H-indole-7-carboxamide for inhibiting IKK2 (aka IKKbeta) |
| US8063071B2 (en) | 2007-10-31 | 2011-11-22 | GlaxoSmithKline, LLC | Chemical compounds |
| CN101304736A (zh) * | 2005-09-07 | 2008-11-12 | 雪兰诺实验室公司 | 治疗子宫内膜异位症的ikk抑制剂 |
| EP3205644A1 (en) | 2005-12-29 | 2017-08-16 | Celtaxsys Inc. | Diamine derivatives as inhibitors of leukotriene a4 hydrolase |
| WO2008002246A1 (en) * | 2006-06-28 | 2008-01-03 | Astrazeneca Ab | A pharmaceutical composition comprising an ikk2 inhibitor and a second active ingrdient. |
| ATE524454T1 (de) * | 2006-11-01 | 2011-09-15 | Chroma Therapeutics Ltd | Inhibitoren von ikk-beta serinthreoninproteinkinase |
| US8003695B2 (en) | 2006-11-01 | 2011-08-23 | Chroma Therapeutics Ltd. | IKK-beta serine-threonine protein kinase inhibitors |
| SG176488A1 (en) * | 2006-11-15 | 2011-12-29 | Virochem Pharma Inc | Thiophene analogues for the treatment or prevention of flavivirus infections |
| CN101583598B (zh) * | 2007-01-15 | 2012-09-12 | 参天制药株式会社 | 具有IκB激酶β抑制活性的新型吲哚衍生物 |
| AR065804A1 (es) | 2007-03-23 | 2009-07-01 | Smithkline Beecham Corp | Compuesto de indol carboxamida, composicion farmaceutica que lo comprende y uso de dicho compuesto para preparar un medicamento |
| MX2010011643A (es) * | 2008-04-26 | 2010-11-30 | Chroma Therapeutics Ltd | Tiofencarboxamidas sustituidas como inhibidores de la proteina cinasa ikk-beta serina, treonina. |
| 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 |
| EP2366699B1 (en) | 2008-10-02 | 2013-08-07 | Asahi Kasei Pharma Corporation | 8-substituted isoquinoline derivative and use thereof |
| US8354539B2 (en) | 2009-03-10 | 2013-01-15 | Glaxo Group Limited | Indole derivatives as IKK2 inhibitors |
| US8410163B2 (en) * | 2009-04-16 | 2013-04-02 | Telik, Inc. | Substituted 4-amino-5-benzoyl-2-(phenylamino)thiophene-3-carbonitriles and substituted 4-amino-5-benzoyl-2-(phenylamino)thiophene-3-carboxamides as tubulin polymerization inhibitors |
| GB0913345D0 (en) | 2009-07-31 | 2009-09-16 | Astrazeneca Ab | New combination 802 |
| WO2011030139A1 (en) | 2009-09-11 | 2011-03-17 | Astrazeneca Ab | 4- (pyrimidin-2-yl) -piperazine and 4- (pyrimidin-2-yl) -piperidine derivatives as gpr119 modulators |
| WO2011061527A1 (en) | 2009-11-17 | 2011-05-26 | Astrazeneca Ab | Combinations comprising a glucocorticoid receptor modulator for the treatment of respiratory diseases |
| 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 |
| JP2012176930A (ja) * | 2010-10-07 | 2012-09-13 | Santen Pharmaceut Co Ltd | 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 |
| GB201016912D0 (en) | 2010-10-07 | 2010-11-24 | Astrazeneca Ab | Novel combination |
| GB201021979D0 (en) | 2010-12-23 | 2011-02-02 | Astrazeneca Ab | New compound |
| GB201021992D0 (en) | 2010-12-23 | 2011-02-02 | Astrazeneca Ab | Compound |
| WO2013138418A2 (en) | 2012-03-14 | 2013-09-19 | Merck Sharp & Dohme Corp. | Process for making cgrp receptor antagonists |
| AU2014249168B2 (en) | 2013-03-12 | 2018-07-12 | Celltaxis, Llc | Methods of inhibiting leukotriene A4 hydrolase |
| MX2015011678A (es) | 2013-03-14 | 2016-07-08 | Celtaxsys Inc | Inhibidores de leucotrieno a4 hidrolasa. |
| EP2968265A4 (en) | 2013-03-14 | 2016-12-28 | Celtaxsys Inc | INHIBITORS OF THE LEUKOTRIEN A4 HYDROLASE |
| AU2014240042C1 (en) | 2013-03-14 | 2019-09-05 | Celltaxis, Llc | Inhibitors of leukotriene A4 hydrolase |
| EP2821791A1 (en) * | 2013-07-04 | 2015-01-07 | Université de Strasbourg | 3-aryl propiolonitrile compounds for thiol labeling |
| MX365614B (es) | 2013-10-17 | 2019-06-07 | Blueprint Medicines Corp | Composiciones utiles para tratar trastornos relacionados con kit. |
| JP6344923B2 (ja) * | 2014-01-29 | 2018-06-20 | 株式会社Uacj | 高強度アルミニウム合金及びその製造方法 |
| ES2913282T3 (es) * | 2014-05-09 | 2022-06-01 | Shanghai Syncores Tech Inc Ltd | Producto intermedio de vortioxetina y procedimiento de síntesis del mismo |
| WO2018183712A1 (en) | 2017-03-31 | 2018-10-04 | Blueprint Medicines Corporation | Pyrrolo[1,2-b]pyridazine compounds and compositions useful for treating disorders related to kit and pdgfr |
| EP3801559B1 (en) | 2018-05-31 | 2025-01-01 | Celltaxis, LLC | Method of reducing pulmonary exacerbations in respiratory disease patients |
| HUE064283T2 (hu) | 2019-04-12 | 2024-02-28 | Blueprint Medicines Corp | Az (S)-1-(4-fluorofenil)-1-(2-(4-(6-(1-metil-1H-pirazol-4-il)pirrolo[2,1-f][1,2,4]triazin-4-il) piperazinil)-pirimidin-5-il)etán-1-amin kristályos formái és elõállítási eljárásai |
| SG11202111244XA (en) | 2019-04-12 | 2021-11-29 | Blueprint Medicines Corp | Pyrrolotriazine derivatives for treating kit- and pdgfra-mediated diseases |
| AR121715A1 (es) | 2020-04-03 | 2022-06-29 | Biocryst Pharm Inc | Pirrolopirimidinaminas como inhibidores del sistema del complemento |
Family Cites Families (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1468012A (en) | 1973-08-09 | 1977-03-23 | Beecham Group Ltd | 2-amino-3-carboxy-thiophene derivatives |
| DE3529247A1 (de) | 1985-05-17 | 1986-11-20 | Bayer Ag, 5090 Leverkusen | Verwendung von thienylharnstoffen und -isoharnstoffen als leistungsfoerdernde mittel bei tieren, neue thienylharnstoffe und -isoharnstoffe und ihre herstellung |
| GB2195634B (en) * | 1986-10-01 | 1990-08-15 | Roussel Lab Ltd | Thiophene derivatives |
| JPH02193990A (ja) * | 1989-01-20 | 1990-07-31 | Taisho Pharmaceut Co Ltd | チオフェンカルボン酸誘導体 |
| US5258357A (en) * | 1989-10-07 | 1993-11-02 | Basf Aktiengesellschaft | Carboxamides, their preparation and their use as herbicides |
| US5378703A (en) * | 1990-04-09 | 1995-01-03 | Alcon Laboratories, Inc. | Sulfonamides useful as carbonic anhydrase inhibitors |
| US5571810A (en) * | 1990-06-11 | 1996-11-05 | Fujisawa Pharmaceutical Co., Ltd. | Thiophene derivatives |
| US5514801A (en) * | 1992-12-29 | 1996-05-07 | Monsanto Company | Cyclic sulfone containing retroviral protease inhibitors |
| JPH09194476A (ja) * | 1996-01-12 | 1997-07-29 | Taisho Pharmaceut Co Ltd | チオフェンアルカン酸誘導体 |
| AU3044197A (en) | 1996-07-11 | 1998-02-09 | Pfizer Inc. | Pyridylpyrrole compounds useful as interleukin- and tnf antagonists |
| PT853083E (pt) * | 1997-01-06 | 2001-12-28 | Pfizer | Composto de piridilfurano e piridiltiofeno e sua utilizacao farmaceutica |
| US6809088B2 (en) * | 1997-03-24 | 2004-10-26 | Societe De Conseils De Recherches Et D'applications Scientifiques (S.C.R.A.S.) | Derivatives of 2-(iminomethyl)amino-phenyl, their preparation, their use as medicaments and the pharmaceutical compositions containing them |
| WO1998046588A2 (en) * | 1997-04-11 | 1998-10-22 | Neorx Corporation | Compounds and therapies for the prevention of vascular and non-vascular pathologies |
| US6037340A (en) | 1997-05-28 | 2000-03-14 | Cadus Pharmaceutical Corporation | Synthesis and use of thiophene- and pyrrole-based heteroaromatic compounds |
| DE19744026A1 (de) | 1997-10-06 | 1999-04-08 | Hoechst Marion Roussel De Gmbh | Pyrazol-Derivate, ihre Herstellung und ihre Verwendung in Arzneimitteln |
| US20020002199A1 (en) * | 1998-03-12 | 2002-01-03 | Lone Jeppesen | Modulators of protein tyrosine phosphatases (ptpases) |
| WO1999046244A1 (en) | 1998-03-12 | 1999-09-16 | Novo Nordisk A/S | Modulators of protein tyrosine phosphatases (ptpases) |
| CZ302691B6 (cs) * | 1998-07-08 | 2011-09-07 | Sanofi - Aventis Deutschland GmbH | N-Arylamidová sloucenina, zpusob její prípravy, farmaceutický prostredek tuto slouceninu obsahující, tato sloucenina pro použití jako aktivátor a pro použití k terapii nebo profylaxi |
| HN2000000051A (es) | 1999-05-19 | 2001-02-02 | Pfizer Prod Inc | Derivados heterociclicos utiles como agentes anticancerosos |
| GB0003154D0 (en) * | 2000-02-12 | 2000-04-05 | Astrazeneca Uk Ltd | Novel compounds |
| GB2361236B (en) * | 2000-03-29 | 2002-04-24 | Cyclacel Ltd | Pyrimidines useful against proliferative disorders |
| US6414013B1 (en) | 2000-06-19 | 2002-07-02 | Pharmacia & Upjohn S.P.A. | Thiophene compounds, process for preparing the same, and pharmaceutical compositions containing the same background of the invention |
| AU2002211663A1 (en) | 2000-10-12 | 2002-04-22 | Smith Kline Beecham Corporation | Nf-$g(k)b inhibitors |
| US20040024047A1 (en) * | 2001-10-12 | 2004-02-05 | Callahan James F. | Nf-kb inhibitors |
| US7122544B2 (en) | 2000-12-06 | 2006-10-17 | Signal Pharmaceuticals, Llc | Anilinopyrimidine derivatives as IKK inhibitors and compositions and methods related thereto |
| US6713638B2 (en) * | 2001-05-18 | 2004-03-30 | Joel M. Linden | 2-amino-3-aroyl-4,5 alkylthiophenes: agonist allosteric enhancers at human A1 adenosine receptors |
| EP2363396A1 (en) * | 2001-06-11 | 2011-09-07 | Virochem Pharma Inc. | Thiophene derivatives as antiviral agents for flavivirus infection |
| SE0102617D0 (sv) | 2001-07-25 | 2001-07-25 | Astrazeneca Ab | Novel compounds |
| SE0102616D0 (sv) | 2001-07-25 | 2001-07-25 | Astrazeneca Ab | Novel compounds |
| WO2003029241A1 (en) * | 2001-10-04 | 2003-04-10 | Smithkline Beecham Corporation | Chk1 kinase inhibitors |
| WO2003028731A1 (en) * | 2001-10-04 | 2003-04-10 | Smithkline Beecham Corporation | Chk1 kinase inhibitors |
| US7166639B2 (en) * | 2001-10-04 | 2007-01-23 | Smithkline Beecham Corporation | NF-κB inhibitors |
| TWI281916B (en) * | 2001-10-25 | 2007-06-01 | Lilly Co Eli | Antitumor compounds and methods |
| US6835745B2 (en) * | 2002-01-15 | 2004-12-28 | Wyeth | Phenyl substituted thiophenes as estrogenic agents |
| US7196106B2 (en) * | 2002-11-05 | 2007-03-27 | Merck & Co., Inc | Cyanothiophene derivatives, compositions containing such compounds and methods of use |
| SE0300091D0 (sv) | 2003-01-15 | 2003-01-15 | Astrazeneca Ab | Novel compounds |
| SE0300092D0 (sv) * | 2003-01-15 | 2003-01-15 | Astrazeneca Ab | Novel compounds |
-
2001
- 2001-07-25 SE SE0102616A patent/SE0102616D0/xx unknown
-
2002
- 2002-07-19 EP EP02751935A patent/EP1421074B1/en not_active Expired - Lifetime
- 2002-07-19 IL IL16002802A patent/IL160028A0/xx unknown
- 2002-07-19 PT PT02751935T patent/PT1421074E/pt unknown
- 2002-07-19 AT AT02751935T patent/ATE482944T1/de active
- 2002-07-19 CN CNB028158369A patent/CN1263751C/zh not_active Expired - Fee Related
- 2002-07-19 NZ NZ530750A patent/NZ530750A/en not_active IP Right Cessation
- 2002-07-19 KR KR1020047001154A patent/KR100931172B1/ko not_active Expired - Fee Related
- 2002-07-19 DK DK02751935.4T patent/DK1421074T3/da active
- 2002-07-19 CA CA2454703A patent/CA2454703C/en not_active Expired - Fee Related
- 2002-07-19 BR BR0211473-9A patent/BR0211473A/pt not_active Application Discontinuation
- 2002-07-19 WO PCT/SE2002/001403 patent/WO2003010158A1/en not_active Ceased
- 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 US US10/484,569 patent/US7125896B2/en not_active Expired - Fee Related
- 2002-07-19 JP JP2003515517A patent/JP4571800B2/ja not_active Expired - Fee Related
- 2002-07-19 DE DE60237828T patent/DE60237828D1/de not_active Expired - Lifetime
- 2002-07-19 MX MXPA04000756A patent/MXPA04000756A/es active IP Right Grant
-
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
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2454703A1 (en) | Novel thiophene carboxamide derivatives | |
| KR101247840B1 (ko) | 아밀로이드 베타 조절제 | |
| CA2917267C (en) | Cyanotriazole compounds | |
| DE69821985T2 (de) | Ortho-anthranilamide derivate als antikoagulantien | |
| DE69615376T2 (de) | Piperazin-derivate als heilmittel | |
| DE69723104T2 (de) | Piridin-2-yl-methylamin-derivate, verfahren zu deren herstellung und ihre verwendung als arzneimittel | |
| DE3875073T2 (de) | 3-(4(1-substituierte-4-piperazinyl)butyl)-4-thiazolidinone, verfahren zu deren herstellung und ihre anwendung als arzneimittel. | |
| US20120214807A1 (en) | Compounds useful as antagonists of ccr2 | |
| CN111196804B (zh) | TGF-βR1抑制剂及其应用 | |
| DE60315062T2 (de) | Triazolverbindungen zur behandlung von dysmenorrhoe | |
| JP2007514690A (ja) | ヒスタミンｈ３アンタゴニストとしてのベンズアゼピン誘導体 | |
| AU2005228290A1 (en) | Tetrahydroquinoline derivatives and a process for preparing the same | |
| JP2007535553A (ja) | アミノ−テトラゾール類縁体および使用方法 | |
| AU2004305079A1 (en) | 3-cycloalkylaminopyrrolidine derivatives as modulators of chemokine receptors | |
| KR20050025189A (ko) | 화학 화합물 | |
| EA007298B1 (ru) | Гетероариламины в качестве ингибиторов гликогенсинтаза-киназы 3-бета (ингибиторов gsk3) | |
| HRP20000014A2 (en) | Triazole compounds and the use thereof as dopamine-d<->3<p>-ligands | |
| JPS61282367A (ja) | ２−チオもしくはオキソ−４−アリ−ルまたはヘテロシクロ−１，５（２ｈ）−ピリミジンジカルボン酸ジエステル類並びに３−アシル−５−ピリミジンカルボン酸類およびエステル類 | |
| CA2647423C (en) | Triazolone derivative | |
| KR20080094806A (ko) | 치환된 이미다졸 유도체 및 이의 ＰＴＰａｓｅ 억제제로서의 용도 | |
| EA037162B1 (ru) | 6-гидрокси-4-оксо-1,4-дигидропиримидин-5-карбоксамиды в качестве агонистов apj | |
| DE602004008291T2 (de) | Substituierte piperidine als histamin-h3-rezeptorliganden | |
| CA2722028C (en) | 5-hydroxypyrimidine-4-carboxamide compound | |
| CZ283993A3 (en) | Phenoxy- and phenoxyalkyl piperidines as antiviral active substances | |
| JP4031814B2 (ja) | ピペリジニルカルボニル−ピロリジンおよびメラノコルチンアゴニストとしてのそれらの使用 |