ES2324879T3 - Derivados de tiofeno benzoimidazol sustituidos con actividad sobre ikk3. - Google Patents

Info

Publication number

ES2324879T3

ES2324879T3 ES05707356T ES05707356T ES2324879T3 ES 2324879 T3 ES2324879 T3 ES 2324879T3 ES 05707356 T ES05707356 T ES 05707356T ES 05707356 T ES05707356 T ES 05707356T ES 2324879 T3 ES2324879 T3 ES 2324879T3

Authority

ES

Spain

Prior art keywords

oxy

benzoimidazol

methyloxy

thiophenecarbonitrile

bis

Prior art date

2004-02-09

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.)

Expired - Lifetime

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• 230000000694 effects Effects 0.000 title description 24
• OHNAITIAQLQHJY-UHFFFAOYSA-N 1h-benzimidazole;thiophene Chemical class C=1C=CSC=1.C1=CC=C2NC=NC2=C1 OHNAITIAQLQHJY-UHFFFAOYSA-N 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 164
• -1 5- [5 , 6-bis (methyloxy) -1H-benzoimidazol-1-yl] -3 - {[(1R) -1- (2-chlorophenyl) ethyl] oxy} -2-thiophenecarbonitrile 5- (1H-benzoimidazol-1-yl ) -3 - [(phenylmethyl) oxy] -2-thiophenecarbonitrile Chemical compound 0.000 claims abstract description 39
• 150000003839 salts Chemical class 0.000 claims abstract description 38
• 239000012453 solvate Substances 0.000 claims abstract description 25
• GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims abstract description 7
• FMWUWNGNNZPAFZ-UHFFFAOYSA-N 5-(5,6-dimethoxybenzimidazol-1-yl)-3-[[2-(trifluoromethoxy)phenyl]methoxy]thiophene-2-carbonitrile Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(SC=1C#N)=CC=1OCC1=CC=CC=C1OC(F)(F)F FMWUWNGNNZPAFZ-UHFFFAOYSA-N 0.000 claims abstract description 5
• DKNHKLFWEYIVEN-UHFFFAOYSA-N 1-[5-cyano-4-[[2-(trifluoromethyl)phenyl]methoxy]thiophen-2-yl]-n-(2-morpholin-4-ylethyl)benzimidazole-5-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1COC1=C(C#N)SC(N2C3=CC=C(C=C3N=C2)C(=O)NCCN2CCOCC2)=C1 DKNHKLFWEYIVEN-UHFFFAOYSA-N 0.000 claims abstract description 4
• ATPCAOKCZJHQPQ-UHFFFAOYSA-N 3-(cyclohexylmethoxy)-5-(5,6-dimethoxybenzimidazol-1-yl)thiophene-2-carbonitrile Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(SC=1C#N)=CC=1OCC1CCCCC1 ATPCAOKCZJHQPQ-UHFFFAOYSA-N 0.000 claims abstract description 4
• PSRPYOGXGJBDNO-IBGZPJMESA-N 3-[(1s)-1-(2-chlorophenyl)butoxy]-5-(5,6-dimethoxybenzimidazol-1-yl)thiophene-2-carbonitrile Chemical compound C1([C@@H](OC2=C(SC(=C2)N2C3=CC(OC)=C(OC)C=C3N=C2)C#N)CCC)=CC=CC=C1Cl PSRPYOGXGJBDNO-IBGZPJMESA-N 0.000 claims abstract description 4
• JXNXCDSAJKBUSO-LLVKDONJSA-N 3-[(2r)-butan-2-yl]oxy-5-(5,6-dimethoxybenzimidazol-1-yl)thiophene-2-carbonitrile Chemical compound S1C(C#N)=C(O[C@H](C)CC)C=C1N1C2=CC(OC)=C(OC)C=C2N=C1 JXNXCDSAJKBUSO-LLVKDONJSA-N 0.000 claims abstract description 4
• NBKRUCSMPTXFAF-UHFFFAOYSA-N 3-[(3-bromopyridin-4-yl)methoxy]-5-(5,6-dimethoxybenzimidazol-1-yl)thiophene-2-carbonitrile Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(SC=1C#N)=CC=1OCC1=CC=NC=C1Br NBKRUCSMPTXFAF-UHFFFAOYSA-N 0.000 claims abstract description 4
• SMNBJSTVVSVRCC-UHFFFAOYSA-N 5-(5,6-dimethoxybenzimidazol-1-yl)-3-(2-morpholin-4-ylethoxy)thiophene-2-carbonitrile Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(SC=1C#N)=CC=1OCCN1CCOCC1 SMNBJSTVVSVRCC-UHFFFAOYSA-N 0.000 claims abstract description 4
• XKXBBFXSVNZXCU-UHFFFAOYSA-N 5-(5,6-dimethoxybenzimidazol-1-yl)-3-(2-phenoxyethoxy)thiophene-2-carbonitrile Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(SC=1C#N)=CC=1OCCOC1=CC=CC=C1 XKXBBFXSVNZXCU-UHFFFAOYSA-N 0.000 claims abstract description 4
• GANNYBUTFKPUEL-UHFFFAOYSA-N 5-(5,6-dimethoxybenzimidazol-1-yl)-3-(2-phenylethoxy)thiophene-2-carbonitrile Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(SC=1C#N)=CC=1OCCC1=CC=CC=C1 GANNYBUTFKPUEL-UHFFFAOYSA-N 0.000 claims abstract description 4
• VHUGSVFKAPEKBW-UHFFFAOYSA-N 5-(5,6-dimethoxybenzimidazol-1-yl)-3-(thiophen-3-ylmethoxy)thiophene-2-carbonitrile Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(SC=1C#N)=CC=1OCC=1C=CSC=1 VHUGSVFKAPEKBW-UHFFFAOYSA-N 0.000 claims abstract description 4
• ZBDAQPLOODCBHP-CYBMUJFWSA-N 5-(5,6-dimethoxybenzimidazol-1-yl)-3-[(1r)-1-[2-(trifluoromethyl)phenyl]ethoxy]thiophene-2-carbonitrile Chemical compound C1([C@@H](C)OC=2C=C(SC=2C#N)N2C=NC=3C=C(C(=CC=32)OC)OC)=CC=CC=C1C(F)(F)F ZBDAQPLOODCBHP-CYBMUJFWSA-N 0.000 claims abstract description 4
• ZZEBGFDCBXKIAE-UHFFFAOYSA-N 5-(5,6-dimethoxybenzimidazol-1-yl)-3-[2-(2-oxopyrrolidin-1-yl)ethoxy]thiophene-2-carbonitrile Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(SC=1C#N)=CC=1OCCN1CCCC1=O ZZEBGFDCBXKIAE-UHFFFAOYSA-N 0.000 claims abstract description 4
• HVBYONAZRGSYTA-UHFFFAOYSA-N 5-(5,6-dimethoxybenzimidazol-1-yl)-3-[[4-(hydroxymethyl)phenyl]methoxy]thiophene-2-carbonitrile Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(SC=1C#N)=CC=1OCC1=CC=C(CO)C=C1 HVBYONAZRGSYTA-UHFFFAOYSA-N 0.000 claims abstract description 4
• MJZWDFWUICERSZ-UHFFFAOYSA-N 5-[6-methoxy-5-(2-morpholin-4-ylethoxy)benzimidazol-1-yl]-3-[[2-(trifluoromethyl)phenyl]methoxy]thiophene-2-carbonitrile Chemical compound COC1=CC=2N(C=3SC(=C(OCC=4C(=CC=CC=4)C(F)(F)F)C=3)C#N)C=NC=2C=C1OCCN1CCOCC1 MJZWDFWUICERSZ-UHFFFAOYSA-N 0.000 claims abstract description 4
• RQAPYNHJWWAJDJ-UHFFFAOYSA-N 3-[(2,5-difluorophenyl)methoxy]-5-(5,6-dimethoxybenzimidazol-1-yl)thiophene-2-carbonitrile Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(SC=1C#N)=CC=1OCC1=CC(F)=CC=C1F RQAPYNHJWWAJDJ-UHFFFAOYSA-N 0.000 claims abstract description 3
• UTZJCFNFCPNUEI-UHFFFAOYSA-N 5-(5,6-dimethoxybenzimidazol-1-yl)-3-[(3-methylbenzotriazol-5-yl)methoxy]thiophene-2-carbonitrile Chemical compound C1=C2N=NN(C)C2=CC(COC=2C=C(SC=2C#N)N2C=NC=3C=C(C(=CC=32)OC)OC)=C1 UTZJCFNFCPNUEI-UHFFFAOYSA-N 0.000 claims abstract description 3
• LXHBSNWDSKZOSV-UHFFFAOYSA-N 5-[5-(3-hydroxypropoxy)-6-methoxybenzimidazol-1-yl]-3-[[2-(trifluoromethyl)phenyl]methoxy]thiophene-2-carbonitrile Chemical compound C1=NC=2C=C(OCCCO)C(OC)=CC=2N1C(SC=1C#N)=CC=1OCC1=CC=CC=C1C(F)(F)F LXHBSNWDSKZOSV-UHFFFAOYSA-N 0.000 claims abstract description 3
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• UBMSMBAYHCLKIK-UHFFFAOYSA-N 5-(5,6-dimethoxybenzimidazol-1-yl)-3-[(2-methoxyphenyl)methoxy]thiophene-2-carbonitrile Chemical compound COC1=CC=CC=C1COC1=C(C#N)SC(N2C3=CC(OC)=C(OC)C=C3N=C2)=C1 UBMSMBAYHCLKIK-UHFFFAOYSA-N 0.000 claims description 4
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