CA2496139C - Benzimidazole derivatives - Google Patents

Info

Publication number

CA2496139C

CA2496139C CA2496139A CA2496139A CA2496139C CA 2496139 C CA2496139 C CA 2496139C CA 2496139 A CA2496139 A CA 2496139A CA 2496139 A CA2496139 A CA 2496139A CA 2496139 C CA2496139 C CA 2496139C

Authority

CA

Canada

Prior art keywords

phenyl

benzimidazol

chlorothiophen

acetamide

oxomorpholin

Prior art date

2002-08-20

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 - Fee Related

Links

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• CIPO
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• 229940058303 antinematodal benzimidazole derivative Drugs 0.000 title description 2
• 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 95
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 19
• 238000011282 treatment Methods 0.000 claims abstract description 16
• 108010074860 Factor Xa Proteins 0.000 claims abstract description 15
• 239000003112 inhibitor Substances 0.000 claims abstract description 4
• -1 piperidinediyl Chemical group 0.000 claims description 358
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 45
• 239000000203 mixture Substances 0.000 claims description 42
• 150000003839 salts Chemical class 0.000 claims description 26
• 125000004076 pyridyl group Chemical group 0.000 claims description 25
• 238000002360 preparation method Methods 0.000 claims description 24
• 239000012453 solvate Substances 0.000 claims description 24
• 239000004480 active ingredient Substances 0.000 claims description 23
• 239000003814 drug Substances 0.000 claims description 23
• 125000004432 carbon atom Chemical group C* 0.000 claims description 20
• 125000000217 alkyl group Chemical group 0.000 claims description 19
• 229910052731 fluorine Inorganic materials 0.000 claims description 19
• 238000000034 method Methods 0.000 claims description 19
• 208000007536 Thrombosis Diseases 0.000 claims description 16
• 125000001544 thienyl group Chemical group 0.000 claims description 14
• 229910052801 chlorine Inorganic materials 0.000 claims description 13
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 13
• 239000002253 acid Substances 0.000 claims description 12
• 229910052794 bromium Inorganic materials 0.000 claims description 12
• 125000002541 furyl group Chemical group 0.000 claims description 12
• 125000002883 imidazolyl group Chemical group 0.000 claims description 12
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 12
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 12
• 125000002971 oxazolyl group Chemical group 0.000 claims description 12
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 12
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 12
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 12
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 12
• 125000000335 thiazolyl group Chemical group 0.000 claims description 12
• 125000004306 triazinyl group Chemical group 0.000 claims description 12
• 238000002399 angioplasty Methods 0.000 claims description 11
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
• 208000010125 myocardial infarction Diseases 0.000 claims description 11
• 206010002383 Angina Pectoris Diseases 0.000 claims description 10
• 206010003210 Arteriosclerosis Diseases 0.000 claims description 10
• 206010061218 Inflammation Diseases 0.000 claims description 10
• 206010022562 Intermittent claudication Diseases 0.000 claims description 10
• 208000011775 arteriosclerosis disease Diseases 0.000 claims description 10
• 229910052739 hydrogen Inorganic materials 0.000 claims description 10
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
• 230000004054 inflammatory process Effects 0.000 claims description 10
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 10
• 208000037803 restenosis Diseases 0.000 claims description 10
• 208000019695 Migraine disease Diseases 0.000 claims description 9
• 125000000520 N-substituted aminocarbonyl group Chemical group [*]NC(=O)* 0.000 claims description 9
• 206010027599 migraine Diseases 0.000 claims description 8
• 125000003277 amino group Chemical group 0.000 claims description 6
• 230000008569 process Effects 0.000 claims description 6
• 229910052740 iodine Inorganic materials 0.000 claims description 5
• 125000006239 protecting group Chemical group 0.000 claims description 5
• BNDUVHSYYBFPGW-UHFFFAOYSA-N 2-[[2-(5-chlorothiophen-2-yl)-3h-benzimidazol-5-yl]oxy]-n-[[4-(2-oxopiperidin-1-yl)phenyl]methyl]acetamide Chemical compound S1C(Cl)=CC=C1C1=NC2=CC(OCC(=O)NCC=3C=CC(=CC=3)N3C(CCCC3)=O)=CC=C2N1 BNDUVHSYYBFPGW-UHFFFAOYSA-N 0.000 claims description 4
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
• ATAKWPWJMUBPFT-UHFFFAOYSA-N 1-[4-[[2-(5-chlorothiophen-2-yl)-3h-benzimidazol-5-yl]methoxy]phenyl]piperidin-2-one Chemical compound S1C(Cl)=CC=C1C1=NC2=CC(COC=3C=CC(=CC=3)N3C(CCCC3)=O)=CC=C2N1 ATAKWPWJMUBPFT-UHFFFAOYSA-N 0.000 claims description 3
• LGHUSLFUQLHXSS-UHFFFAOYSA-N 1-[4-[[[2-(5-chlorothiophen-2-yl)-3h-benzimidazol-5-yl]methylamino]methyl]phenyl]piperidin-2-one Chemical compound S1C(Cl)=CC=C1C1=NC2=CC(CNCC=3C=CC(=CC=3)N3C(CCCC3)=O)=CC=C2N1 LGHUSLFUQLHXSS-UHFFFAOYSA-N 0.000 claims description 3
• VDHKRDZLVXYTRJ-UHFFFAOYSA-N 2-(5-chlorothiophen-2-yl)-n-[[4-(2-oxopiperidin-1-yl)phenyl]methyl]-3h-benzimidazole-5-carboxamide Chemical compound S1C(Cl)=CC=C1C1=NC2=CC(C(=O)NCC=3C=CC(=CC=3)N3C(CCCC3)=O)=CC=C2N1 VDHKRDZLVXYTRJ-UHFFFAOYSA-N 0.000 claims description 3
• OHFMFUJGVXCEBF-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)-3h-benzimidazol-5-yl]-n-[3-methyl-4-(3-oxomorpholin-4-yl)phenyl]acetamide Chemical compound C=1C=C(N2C(COCC2)=O)C(C)=CC=1NC(=O)CC(C=C1N=2)=CC=C1NC=2C1=CC=C(Cl)C=C1 OHFMFUJGVXCEBF-UHFFFAOYSA-N 0.000 claims description 3
• LAKOQFRATQEDPO-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)-3h-benzimidazol-5-yl]-n-[4-(3-oxomorpholin-4-yl)phenyl]acetamide Chemical compound C1=CC(Cl)=CC=C1C1=NC2=CC(CC(=O)NC=3C=CC(=CC=3)N3C(COCC3)=O)=CC=C2N1 LAKOQFRATQEDPO-UHFFFAOYSA-N 0.000 claims description 3
• NDZLXVSVGYNDTC-UHFFFAOYSA-N 2-[2-(5-chloropyridin-2-yl)-3h-benzimidazol-5-yl]-n-[3-methyl-4-(3-oxomorpholin-4-yl)phenyl]acetamide Chemical compound C=1C=C(N2C(COCC2)=O)C(C)=CC=1NC(=O)CC(C=C1N=2)=CC=C1NC=2C1=CC=C(Cl)C=N1 NDZLXVSVGYNDTC-UHFFFAOYSA-N 0.000 claims description 3
• INLIPNBBIONHPS-UHFFFAOYSA-N 2-[2-(5-chloropyridin-2-yl)-3h-benzimidazol-5-yl]-n-[4-(3-oxomorpholin-4-yl)phenyl]acetamide Chemical compound N1=CC(Cl)=CC=C1C1=NC2=CC(CC(=O)NC=3C=CC(=CC=3)N3C(COCC3)=O)=CC=C2N1 INLIPNBBIONHPS-UHFFFAOYSA-N 0.000 claims description 3
• CVKABHBQSLFBAR-UHFFFAOYSA-N 2-[2-(5-chlorothiophen-2-yl)-3h-benzimidazol-5-yl]-n-[3-methyl-4-(3-oxomorpholin-4-yl)phenyl]acetamide Chemical compound C=1C=C(N2C(COCC2)=O)C(C)=CC=1NC(=O)CC(C=C1N=2)=CC=C1NC=2C1=CC=C(Cl)S1 CVKABHBQSLFBAR-UHFFFAOYSA-N 0.000 claims description 3
• NLFMHTGAWNOQBL-UHFFFAOYSA-N 2-[2-(5-chlorothiophen-2-yl)-3h-benzimidazol-5-yl]-n-[4-(2-iminopiperidin-1-yl)phenyl]acetamide Chemical compound S1C(Cl)=CC=C1C1=NC2=CC(CC(=O)NC=3C=CC(=CC=3)N3C(CCCC3)=N)=CC=C2N1 NLFMHTGAWNOQBL-UHFFFAOYSA-N 0.000 claims description 3
• FUHBDFWYHPCRRE-UHFFFAOYSA-N 2-[2-(5-chlorothiophen-2-yl)-3h-benzimidazol-5-yl]-n-[4-(2-iminopyrrolidin-1-yl)phenyl]acetamide Chemical compound S1C(Cl)=CC=C1C1=NC2=CC(CC(=O)NC=3C=CC(=CC=3)N3C(CCC3)=N)=CC=C2N1 FUHBDFWYHPCRRE-UHFFFAOYSA-N 0.000 claims description 3
• FEMYQMPDVJBTJX-UHFFFAOYSA-N 2-[2-(5-chlorothiophen-2-yl)-3h-benzimidazol-5-yl]-n-[4-(2-oxopyrazin-1-yl)phenyl]acetamide Chemical compound S1C(Cl)=CC=C1C1=NC2=CC(CC(=O)NC=3C=CC(=CC=3)N3C(C=NC=C3)=O)=CC=C2N1 FEMYQMPDVJBTJX-UHFFFAOYSA-N 0.000 claims description 3
• JLXGEDHKNZOFGL-UHFFFAOYSA-N 2-[2-(5-chlorothiophen-2-yl)-3h-benzimidazol-5-yl]-n-[4-(3-oxomorpholin-4-yl)phenyl]acetamide Chemical compound S1C(Cl)=CC=C1C1=NC2=CC(CC(=O)NC=3C=CC(=CC=3)N3C(COCC3)=O)=CC=C2N1 JLXGEDHKNZOFGL-UHFFFAOYSA-N 0.000 claims description 3
• ZZPAQLRMDURSEI-UHFFFAOYSA-N 2-[2-(5-chlorothiophen-2-yl)-3h-benzimidazol-5-yl]-n-[4-(3-oxomorpholin-4-yl)phenyl]pentanamide Chemical compound C=1C=C2NC(C=3SC(Cl)=CC=3)=NC2=CC=1C(CCC)C(=O)NC(C=C1)=CC=C1N1CCOCC1=O ZZPAQLRMDURSEI-UHFFFAOYSA-N 0.000 claims description 3
• RBCYZKNHQRAQLZ-UHFFFAOYSA-N 2-[2-(5-chlorothiophen-2-yl)-3h-benzimidazol-5-yl]-n-[[4-(3-oxomorpholin-4-yl)phenyl]methyl]acetamide Chemical compound S1C(Cl)=CC=C1C1=NC2=CC(CC(=O)NCC=3C=CC(=CC=3)N3C(COCC3)=O)=CC=C2N1 RBCYZKNHQRAQLZ-UHFFFAOYSA-N 0.000 claims description 3
• JYHSGSGMXPVSPT-UHFFFAOYSA-N 2-[[2-(5-chlorothiophen-2-yl)-3h-benzimidazol-5-yl]amino]-n-[4-(3-oxomorpholin-4-yl)phenyl]acetamide Chemical compound S1C(Cl)=CC=C1C1=NC2=CC(NCC(=O)NC=3C=CC(=CC=3)N3C(COCC3)=O)=CC=C2N1 JYHSGSGMXPVSPT-UHFFFAOYSA-N 0.000 claims description 3
• SONYDGYZKVDEEN-UHFFFAOYSA-N 2-[[2-(5-chlorothiophen-2-yl)-3h-benzimidazol-5-yl]oxy]-n-[4-(3-oxomorpholin-4-yl)phenyl]acetamide Chemical compound S1C(Cl)=CC=C1C1=NC2=CC(OCC(=O)NC=3C=CC(=CC=3)N3C(COCC3)=O)=CC=C2N1 SONYDGYZKVDEEN-UHFFFAOYSA-N 0.000 claims description 3
• UNDCOWFZSXBJJF-UHFFFAOYSA-N 2-[[2-(5-chlorothiophen-2-yl)-3h-benzimidazol-5-yl]oxy]-n-[4-(3-oxomorpholin-4-yl)phenyl]pentanamide Chemical compound C=1C=C(N2C(COCC2)=O)C=CC=1NC(=O)C(CCC)OC(C=C1N=2)=CC=C1NC=2C1=CC=C(Cl)S1 UNDCOWFZSXBJJF-UHFFFAOYSA-N 0.000 claims description 3
• KTDWHOFOHNWSMC-UHFFFAOYSA-N 2-[[2-(5-chlorothiophen-2-yl)-3h-benzimidazol-5-yl]sulfonyl]-n-[3-methyl-4-(3-oxomorpholin-4-yl)phenyl]acetamide Chemical compound C=1C=C(N2C(COCC2)=O)C(C)=CC=1NC(=O)CS(=O)(=O)C(C=C1N=2)=CC=C1NC=2C1=CC=C(Cl)S1 KTDWHOFOHNWSMC-UHFFFAOYSA-N 0.000 claims description 3
• GPNOAROJFAEWFS-UHFFFAOYSA-N 1-[4-[[2-(5-chlorothiophen-2-yl)-3h-benzimidazol-5-yl]amino]phenyl]piperidin-2-one Chemical compound S1C(Cl)=CC=C1C1=NC2=CC(NC=3C=CC(=CC=3)N3C(CCCC3)=O)=CC=C2N1 GPNOAROJFAEWFS-UHFFFAOYSA-N 0.000 claims description 2
• UNQMKHXVPSVSKD-UHFFFAOYSA-N 1-[4-[[2-(5-chlorothiophen-2-yl)-3h-benzimidazol-5-yl]oxy]phenyl]piperidin-2-one Chemical compound S1C(Cl)=CC=C1C1=NC2=CC(OC=3C=CC(=CC=3)N3C(CCCC3)=O)=CC=C2N1 UNQMKHXVPSVSKD-UHFFFAOYSA-N 0.000 claims description 2
• GEIOUZHNIQBXPT-UHFFFAOYSA-N 2-[2-(5-bromothiophen-2-yl)-3h-benzimidazol-5-yl]-n-[3-methyl-4-(3-oxomorpholin-4-yl)phenyl]acetamide Chemical compound C=1C=C(N2C(COCC2)=O)C(C)=CC=1NC(=O)CC(C=C1N=2)=CC=C1NC=2C1=CC=C(Br)S1 GEIOUZHNIQBXPT-UHFFFAOYSA-N 0.000 claims description 2
• KVQPKABEOHAPGU-UHFFFAOYSA-N 2-[2-(5-bromothiophen-2-yl)-3h-benzimidazol-5-yl]-n-[4-(2-oxopiperidin-1-yl)phenyl]acetamide Chemical compound S1C(Br)=CC=C1C1=NC2=CC(CC(=O)NC=3C=CC(=CC=3)N3C(CCCC3)=O)=CC=C2N1 KVQPKABEOHAPGU-UHFFFAOYSA-N 0.000 claims description 2
• USIINOACWLOALU-UHFFFAOYSA-N 2-[2-(5-bromothiophen-2-yl)-3h-benzimidazol-5-yl]-n-[4-(2-oxopyridin-1-yl)phenyl]acetamide Chemical compound S1C(Br)=CC=C1C1=NC2=CC(CC(=O)NC=3C=CC(=CC=3)N3C(C=CC=C3)=O)=CC=C2N1 USIINOACWLOALU-UHFFFAOYSA-N 0.000 claims description 2
• PKKIORNIFRCVJP-UHFFFAOYSA-N 2-[2-(5-bromothiophen-2-yl)-3h-benzimidazol-5-yl]-n-[4-(3-oxomorpholin-4-yl)phenyl]acetamide Chemical compound S1C(Br)=CC=C1C1=NC2=CC(CC(=O)NC=3C=CC(=CC=3)N3C(COCC3)=O)=CC=C2N1 PKKIORNIFRCVJP-UHFFFAOYSA-N 0.000 claims description 2
• CJBUNOIFLCWFHW-UHFFFAOYSA-N 2-[2-(5-bromothiophen-2-yl)-3h-benzimidazol-5-yl]-n-[[4-(2-oxopiperidin-1-yl)phenyl]methyl]acetamide Chemical compound S1C(Br)=CC=C1C1=NC2=CC(CC(=O)NCC=3C=CC(=CC=3)N3C(CCCC3)=O)=CC=C2N1 CJBUNOIFLCWFHW-UHFFFAOYSA-N 0.000 claims description 2
• VWZRQESWIIHOJO-UHFFFAOYSA-N 2-[2-(5-chlorothiophen-2-yl)-3h-benzimidazol-5-yl]-n-[3-methyl-4-(2-oxopyrrolidin-1-yl)phenyl]acetamide Chemical compound C=1C=C(N2C(CCC2)=O)C(C)=CC=1NC(=O)CC(C=C1N=2)=CC=C1NC=2C1=CC=C(Cl)S1 VWZRQESWIIHOJO-UHFFFAOYSA-N 0.000 claims description 2
• ZMJLJYQNDNYWST-UHFFFAOYSA-N 2-[2-(5-chlorothiophen-2-yl)-3h-benzimidazol-5-yl]-n-[4-(2-iminopiperidin-1-yl)phenyl]pentanamide Chemical compound C=1C=C2NC(C=3SC(Cl)=CC=3)=NC2=CC=1C(CCC)C(=O)NC(C=C1)=CC=C1N1CCCCC1=N ZMJLJYQNDNYWST-UHFFFAOYSA-N 0.000 claims description 2
• UFSNUSZAUNPASQ-UHFFFAOYSA-N 2-[2-(5-chlorothiophen-2-yl)-3h-benzimidazol-5-yl]-n-[4-(2-oxopiperidin-1-yl)phenyl]acetamide Chemical compound S1C(Cl)=CC=C1C1=NC2=CC(CC(=O)NC=3C=CC(=CC=3)N3C(CCCC3)=O)=CC=C2N1 UFSNUSZAUNPASQ-UHFFFAOYSA-N 0.000 claims description 2
• ACKCYLQIKBMOKJ-UHFFFAOYSA-N 2-[2-(5-chlorothiophen-2-yl)-3h-benzimidazol-5-yl]-n-[4-(2-oxopyridin-1-yl)phenyl]acetamide Chemical compound S1C(Cl)=CC=C1C1=NC2=CC(CC(=O)NC=3C=CC(=CC=3)N3C(C=CC=C3)=O)=CC=C2N1 ACKCYLQIKBMOKJ-UHFFFAOYSA-N 0.000 claims description 2
• ZUSXGOOVZNWGPQ-UHFFFAOYSA-N 2-[2-(5-chlorothiophen-2-yl)-3h-benzimidazol-5-yl]-n-[4-(2-oxopyrrolidin-1-yl)phenyl]acetamide Chemical compound S1C(Cl)=CC=C1C1=NC2=CC(CC(=O)NC=3C=CC(=CC=3)N3C(CCC3)=O)=CC=C2N1 ZUSXGOOVZNWGPQ-UHFFFAOYSA-N 0.000 claims description 2
• TWIGIXZMJGFYBB-UHFFFAOYSA-N 2-[2-(5-chlorothiophen-2-yl)-3h-benzimidazol-5-yl]-n-[4-(3-oxomorpholin-4-yl)phenyl]-3-phenylpropanamide Chemical compound S1C(Cl)=CC=C1C1=NC2=CC(C(CC=3C=CC=CC=3)C(=O)NC=3C=CC(=CC=3)N3C(COCC3)=O)=CC=C2N1 TWIGIXZMJGFYBB-UHFFFAOYSA-N 0.000 claims description 2
• RDEJTJDJEFIYSM-UHFFFAOYSA-N 2-[2-(5-chlorothiophen-2-yl)-3h-benzimidazol-5-yl]-n-[[4-(2-oxopiperidin-1-yl)phenyl]methyl]acetamide Chemical compound S1C(Cl)=CC=C1C1=NC2=CC(CC(=O)NCC=3C=CC(=CC=3)N3C(CCCC3)=O)=CC=C2N1 RDEJTJDJEFIYSM-UHFFFAOYSA-N 0.000 claims description 2
• HZVZDKUIBXHFOF-UHFFFAOYSA-N 2-[[2-(5-chlorothiophen-2-yl)-3h-benzimidazol-5-yl]oxy]-n-[3-fluoro-4-(3-oxomorpholin-4-yl)phenyl]pentanamide Chemical compound C=1C=C(N2C(COCC2)=O)C(F)=CC=1NC(=O)C(CCC)OC(C=C1N=2)=CC=C1NC=2C1=CC=C(Cl)S1 HZVZDKUIBXHFOF-UHFFFAOYSA-N 0.000 claims description 2
• OZVIVMCNSAPOTE-UHFFFAOYSA-N 2-[[2-(5-chlorothiophen-2-yl)-3h-benzimidazol-5-yl]oxy]-n-[3-methyl-4-(3-oxomorpholin-4-yl)phenyl]acetamide Chemical compound C=1C=C(N2C(COCC2)=O)C(C)=CC=1NC(=O)COC(C=C1N=2)=CC=C1NC=2C1=CC=C(Cl)S1 OZVIVMCNSAPOTE-UHFFFAOYSA-N 0.000 claims description 2
• GWDPIDQBZCTRRE-UHFFFAOYSA-N 2-[[2-(5-chlorothiophen-2-yl)-3h-benzimidazol-5-yl]oxy]-n-[4-(2-iminopiperidin-1-yl)phenyl]acetamide Chemical compound S1C(Cl)=CC=C1C1=NC2=CC(OCC(=O)NC=3C=CC(=CC=3)N3C(CCCC3)=N)=CC=C2N1 GWDPIDQBZCTRRE-UHFFFAOYSA-N 0.000 claims description 2
• FVSHAOPDOUDOKQ-UHFFFAOYSA-N 2-[[2-(5-chlorothiophen-2-yl)-3h-benzimidazol-5-yl]oxy]-n-[4-(2-oxopyrazin-1-yl)phenyl]acetamide Chemical compound S1C(Cl)=CC=C1C1=NC2=CC(OCC(=O)NC=3C=CC(=CC=3)N3C(C=NC=C3)=O)=CC=C2N1 FVSHAOPDOUDOKQ-UHFFFAOYSA-N 0.000 claims description 2
• JIFJPZXNKKLYMT-UHFFFAOYSA-N 2-[[2-(5-chlorothiophen-2-yl)-3h-benzimidazol-5-yl]sulfonyl]-n-[4-(2-oxopyridin-1-yl)phenyl]acetamide Chemical compound S1C(Cl)=CC=C1C1=NC2=CC(S(=O)(=O)CC(=O)NC=3C=CC(=CC=3)N3C(C=CC=C3)=O)=CC=C2N1 JIFJPZXNKKLYMT-UHFFFAOYSA-N 0.000 claims description 2
• BZCYFEJBZOTWDL-UHFFFAOYSA-N 2-[[2-(5-chlorothiophen-2-yl)-3h-benzimidazol-5-yl]sulfonyl]-n-[4-(3-oxomorpholin-4-yl)phenyl]acetamide Chemical compound S1C(Cl)=CC=C1C1=NC2=CC(S(=O)(=O)CC(=O)NC=3C=CC(=CC=3)N3C(COCC3)=O)=CC=C2N1 BZCYFEJBZOTWDL-UHFFFAOYSA-N 0.000 claims description 2
• BBVCWQVIBCBAFF-UHFFFAOYSA-N 2-[[2-(5-chlorothiophen-2-yl)-3h-benzimidazol-5-yl]sulfonyl]-n-[[4-(2-oxopiperidin-1-yl)phenyl]methyl]acetamide Chemical compound S1C(Cl)=CC=C1C1=NC2=CC(S(=O)(=O)CC(=O)NCC=3C=CC(=CC=3)N3C(CCCC3)=O)=CC=C2N1 BBVCWQVIBCBAFF-UHFFFAOYSA-N 0.000 claims description 2
• NRTBIAQMXRWMFA-UHFFFAOYSA-N 3-[2-(5-chlorothiophen-2-yl)-3h-benzimidazol-5-yl]-n-[3-methyl-4-(3-oxomorpholin-4-yl)phenyl]propanamide Chemical compound C=1C=C(N2C(COCC2)=O)C(C)=CC=1NC(=O)CCC(C=C1N=2)=CC=C1NC=2C1=CC=C(Cl)S1 NRTBIAQMXRWMFA-UHFFFAOYSA-N 0.000 claims description 2
• XCRMSONDHWBPJX-UHFFFAOYSA-N 3-[2-(5-chlorothiophen-2-yl)-3h-benzimidazol-5-yl]-n-[4-(3-oxomorpholin-4-yl)phenyl]propanamide Chemical compound S1C(Cl)=CC=C1C1=NC2=CC(CCC(=O)NC=3C=CC(=CC=3)N3C(COCC3)=O)=CC=C2N1 XCRMSONDHWBPJX-UHFFFAOYSA-N 0.000 claims description 2
• 101100294102 Caenorhabditis elegans nhr-2 gene Proteins 0.000 claims description 2
• 108010054265 Factor VIIa Proteins 0.000 claims description 2
• ZGDKIPGELVKHRS-UHFFFAOYSA-N n-[2-(5-chlorothiophen-2-yl)-3h-benzimidazol-5-yl]-2-[4-(3-oxomorpholin-4-yl)phenyl]acetamide Chemical compound S1C(Cl)=CC=C1C1=NC2=CC(NC(=O)CC=3C=CC(=CC=3)N3C(COCC3)=O)=CC=C2N1 ZGDKIPGELVKHRS-UHFFFAOYSA-N 0.000 claims description 2
• DXDZGWWHEWUNOA-UHFFFAOYSA-N n-[2-(5-chlorothiophen-2-yl)-3h-benzimidazol-5-yl]-4-(2-oxopiperidin-1-yl)benzamide Chemical compound S1C(Cl)=CC=C1C1=NC2=CC(NC(=O)C=3C=CC(=CC=3)N3C(CCCC3)=O)=CC=C2N1 DXDZGWWHEWUNOA-UHFFFAOYSA-N 0.000 claims description 2
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