DE60221866T2 - 2-PHENYL BENZIMIDAZOLE UND IMIDAZO-i4,5ö-PYRIDINE ALS CDS1/CHK2-INHIBITOREN UND ADJUVANTIEN IN DER CHEMOTHERAPIE ODER STRAHLUNGSTHERAPIE ZUR BEHANDLUNG VON KREBS - Google Patents

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Publication number

DE60221866T2

DE60221866T2 DE60221866T DE60221866T DE60221866T2 DE 60221866 T2 DE60221866 T2 DE 60221866T2 DE 60221866 T DE60221866 T DE 60221866T DE 60221866 T DE60221866 T DE 60221866T DE 60221866 T2 DE60221866 T2 DE 60221866T2

Authority

DE

Germany

Prior art keywords

phenyl

benzoimidazole

carboxamide

chloro

carboxylic acid

Prior art date

2001-10-19

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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• 206010028980 Neoplasm Diseases 0.000 title claims abstract description 45
• 238000011282 treatment Methods 0.000 title claims abstract description 31
• 201000011510 cancer Diseases 0.000 title claims abstract description 27
• 239000003112 inhibitor Substances 0.000 title abstract description 5
• 238000002512 chemotherapy Methods 0.000 title abstract 2
• 238000001959 radiotherapy Methods 0.000 title abstract 2
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title description 13
• 102100031075 Serine/threonine-protein kinase Chk2 Human genes 0.000 title description 3
• 101000777277 Homo sapiens Serine/threonine-protein kinase Chk2 Proteins 0.000 title description 2
• DWYHDSLIWMUSOO-UHFFFAOYSA-N 2-phenyl-1h-benzimidazole Chemical compound C1=CC=CC=C1C1=NC2=CC=CC=C2N1 DWYHDSLIWMUSOO-UHFFFAOYSA-N 0.000 title 1
• 101710178747 Phosphatidate cytidylyltransferase 1 Proteins 0.000 title 1
• -1 -SCF 3 Chemical group 0.000 claims description 279
• 150000001875 compounds Chemical class 0.000 claims description 211
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 51
• 125000000217 alkyl group Chemical group 0.000 claims description 39
• 229910052799 carbon Inorganic materials 0.000 claims description 38
• 125000003118 aryl group Chemical group 0.000 claims description 28
• 229910052757 nitrogen Inorganic materials 0.000 claims description 26
• 150000001721 carbon Chemical group 0.000 claims description 22
• 229910052739 hydrogen Inorganic materials 0.000 claims description 22
• 125000004432 carbon atom Chemical group C* 0.000 claims description 20
• 150000001408 amides Chemical class 0.000 claims description 16
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
• 150000003839 salts Chemical class 0.000 claims description 15
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
• 229910052727 yttrium Inorganic materials 0.000 claims description 14
• 229910052760 oxygen Inorganic materials 0.000 claims description 13
• 125000004076 pyridyl group Chemical group 0.000 claims description 12
• 229910052717 sulfur Inorganic materials 0.000 claims description 12
• 150000002148 esters Chemical class 0.000 claims description 11
• 125000002950 monocyclic group Chemical group 0.000 claims description 11
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
• 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 10
• 125000002541 furyl group Chemical group 0.000 claims description 10
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 10
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 9
• 125000001544 thienyl group Chemical group 0.000 claims description 9
• OFXZKDLRVIQUDZ-UHFFFAOYSA-N 2-[4-(4-methoxyphenyl)sulfanylphenyl]-3h-benzimidazole-5-carboxamide Chemical compound C1=CC(OC)=CC=C1SC1=CC=C(C=2NC3=CC=C(C=C3N=2)C(N)=O)C=C1 OFXZKDLRVIQUDZ-UHFFFAOYSA-N 0.000 claims description 8
• 125000002883 imidazolyl group Chemical group 0.000 claims description 8
• JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 claims description 8
• 125000000335 thiazolyl group Chemical group 0.000 claims description 8
• 229910052801 chlorine Inorganic materials 0.000 claims description 7
• WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 claims description 7
• 150000002430 hydrocarbons Chemical group 0.000 claims description 7
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 7
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 7
• 125000002971 oxazolyl group Chemical group 0.000 claims description 7
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 7
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 7
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 7
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
• 125000001424 substituent group Chemical group 0.000 claims description 7
• UXGJAOIJSROTTN-UHFFFAOYSA-N 2-[4-(4-chlorophenoxy)phenyl]-3h-benzimidazole-5-carboxamide Chemical compound N1C2=CC(C(=O)N)=CC=C2N=C1C(C=C1)=CC=C1OC1=CC=C(Cl)C=C1 UXGJAOIJSROTTN-UHFFFAOYSA-N 0.000 claims description 6
• IYDLNJYJAXUZOJ-UHFFFAOYSA-N 2-[4-(4-chlorophenoxy)phenyl]-3h-benzimidazole-5-carboxylic acid Chemical compound N=1C2=CC(C(=O)O)=CC=C2NC=1C(C=C1)=CC=C1OC1=CC=C(Cl)C=C1 IYDLNJYJAXUZOJ-UHFFFAOYSA-N 0.000 claims description 6
• 229910052731 fluorine Inorganic materials 0.000 claims description 6
• ZVKFEOMYLFFRRO-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)sulfonylphenyl]-3h-benzimidazole-5-carboxylic acid Chemical compound N=1C2=CC(C(=O)O)=CC=C2NC=1C(C=C1)=CC=C1S(=O)(=O)C1=CC=C(Cl)C=C1 ZVKFEOMYLFFRRO-UHFFFAOYSA-N 0.000 claims description 5
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 5
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 5
• 239000003814 drug Substances 0.000 claims description 5
• 239000001257 hydrogen Substances 0.000 claims description 5
• QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 claims description 4
• OCZLENVYJYOFND-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenoxy)phenyl]-1h-imidazo[4,5-b]pyridine-5-carboxamide Chemical compound N=1C2=NC(C(=O)N)=CC=C2NC=1C(C=C1)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 OCZLENVYJYOFND-UHFFFAOYSA-N 0.000 claims description 4
• GGGHAUOZPNLVBZ-UHFFFAOYSA-N 2-[4-(4-bromo-3-methoxyphenoxy)phenyl]-3h-benzimidazole-5-carboxamide Chemical compound C1=C(Br)C(OC)=CC(OC=2C=CC(=CC=2)C=2NC3=CC=C(C=C3N=2)C(N)=O)=C1 GGGHAUOZPNLVBZ-UHFFFAOYSA-N 0.000 claims description 4
• QVTSHHGQQUXMMU-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)sulfinylphenyl]-3h-benzimidazole-5-carboxylic acid Chemical compound N=1C2=CC(C(=O)O)=CC=C2NC=1C(C=C1)=CC=C1S(=O)C1=CC=C(Cl)C=C1 QVTSHHGQQUXMMU-UHFFFAOYSA-N 0.000 claims description 4
• OEVNSTIIQXLQST-UHFFFAOYSA-N 2-[4-(4-methoxyphenoxy)phenyl]-3h-benzimidazole-5-carboxylic acid Chemical compound C1=CC(OC)=CC=C1OC1=CC=C(C=2NC3=CC=C(C=C3N=2)C(O)=O)C=C1 OEVNSTIIQXLQST-UHFFFAOYSA-N 0.000 claims description 4
• XCICTQGKGKMDPL-UHFFFAOYSA-N 2-[4-(4-phenylpiperazin-1-yl)phenyl]-3h-benzimidazole-5-carboxamide Chemical compound N=1C2=CC(C(=O)N)=CC=C2NC=1C(C=C1)=CC=C1N(CC1)CCN1C1=CC=CC=C1 XCICTQGKGKMDPL-UHFFFAOYSA-N 0.000 claims description 4
• DBXRQSUMLUDDFF-UHFFFAOYSA-N 2-[4-(phenylcarbamoyl)phenyl]-3h-benzimidazole-5-carboxamide Chemical compound N=1C2=CC(C(=O)N)=CC=C2NC=1C(C=C1)=CC=C1C(=O)NC1=CC=CC=C1 DBXRQSUMLUDDFF-UHFFFAOYSA-N 0.000 claims description 4
• DZICGNYWCKQHLC-UHFFFAOYSA-N 2-[4-[(3,4-dichlorophenyl)sulfamoyl]phenyl]-3h-benzimidazole-5-carboxamide Chemical compound N=1C2=CC(C(=O)N)=CC=C2NC=1C(C=C1)=CC=C1S(=O)(=O)NC1=CC=C(Cl)C(Cl)=C1 DZICGNYWCKQHLC-UHFFFAOYSA-N 0.000 claims description 4
• KQWNAIXXEHWAEW-UHFFFAOYSA-N 2-[4-[(3,4-dichlorophenyl)sulfonylamino]phenyl]-3h-benzimidazole-5-carboxamide Chemical compound N=1C2=CC(C(=O)N)=CC=C2NC=1C(C=C1)=CC=C1NS(=O)(=O)C1=CC=C(Cl)C(Cl)=C1 KQWNAIXXEHWAEW-UHFFFAOYSA-N 0.000 claims description 4
• KHJVRUYUSFNQOV-UHFFFAOYSA-N 2-[4-[(4-chlorophenyl)sulfamoyl]phenyl]-3h-benzimidazole-5-carboxamide Chemical compound N=1C2=CC(C(=O)N)=CC=C2NC=1C(C=C1)=CC=C1S(=O)(=O)NC1=CC=C(Cl)C=C1 KHJVRUYUSFNQOV-UHFFFAOYSA-N 0.000 claims description 4
• MXWLUBDXXFDAMW-UHFFFAOYSA-N 2-[4-[4-(4-fluorophenyl)piperazin-1-yl]phenyl]-3h-benzimidazole-5-carboxamide Chemical compound N=1C2=CC(C(=O)N)=CC=C2NC=1C(C=C1)=CC=C1N(CC1)CCN1C1=CC=C(F)C=C1 MXWLUBDXXFDAMW-UHFFFAOYSA-N 0.000 claims description 4
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 4
• YYFLDZZDOUDZQM-UHFFFAOYSA-N 3-[1-[[4-(3-phenylquinolin-2-yl)phenyl]methyl]piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound O=C1NC2=CC=CC=C2N1C(CC1)CCN1CC(C=C1)=CC=C1C1=NC2=CC=CC=C2C=C1C1=CC=CC=C1 YYFLDZZDOUDZQM-UHFFFAOYSA-N 0.000 claims description 4
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 4
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
• PQEQTUGNXSXNOM-UHFFFAOYSA-N 6-chloro-2-[4-(3,4-dichlorophenoxy)phenyl]-1h-benzimidazole-5-carboxamide Chemical compound N1C=2C=C(Cl)C(C(=O)N)=CC=2N=C1C(C=C1)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 PQEQTUGNXSXNOM-UHFFFAOYSA-N 0.000 claims description 4
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
• 229910052740 iodine Inorganic materials 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
• 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 4
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 4
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 3
• PJGNWTVDWTYPDG-UHFFFAOYSA-N 2-(4-naphthalen-2-yloxyphenyl)-3h-benzimidazole-5-carboxamide Chemical compound C1=CC=CC2=CC(OC3=CC=C(C=C3)C=3NC4=CC=C(C=C4N=3)C(=O)N)=CC=C21 PJGNWTVDWTYPDG-UHFFFAOYSA-N 0.000 claims description 3
• FYJXNYHANMMZPJ-UHFFFAOYSA-N 2-(4-naphthalen-2-yloxyphenyl)-3h-benzimidazole-5-sulfonamide Chemical compound C1=CC=CC2=CC(OC3=CC=C(C=C3)C=3NC4=CC=C(C=C4N=3)S(=O)(=O)N)=CC=C21 FYJXNYHANMMZPJ-UHFFFAOYSA-N 0.000 claims description 3
• KHHZVSIVKKGELQ-UHFFFAOYSA-N 2-(4-phenoxyphenyl)-3h-benzimidazole-5-sulfonamide Chemical compound N=1C2=CC(S(=O)(=O)N)=CC=C2NC=1C(C=C1)=CC=C1OC1=CC=CC=C1 KHHZVSIVKKGELQ-UHFFFAOYSA-N 0.000 claims description 3
• YZBXZQMJLCGDHP-UHFFFAOYSA-N 2-(4-pyridin-3-yloxyphenyl)-3h-benzimidazole-5-carboxamide Chemical compound N=1C2=CC(C(=O)N)=CC=C2NC=1C(C=C1)=CC=C1OC1=CC=CN=C1 YZBXZQMJLCGDHP-UHFFFAOYSA-N 0.000 claims description 3
• HFODTOJSGSGHID-UHFFFAOYSA-N 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-3h-benzimidazole-5-carboxamide Chemical compound N=1C2=CC(C(=O)N)=CC=C2NC=1C(C(=C1)Cl)=CC=C1OC1=CC=C(Cl)C=C1 HFODTOJSGSGHID-UHFFFAOYSA-N 0.000 claims description 3
• GCKIINJXIXPHKJ-UHFFFAOYSA-N 2-[3-chloro-4-(2-methoxy-4-methylphenoxy)phenyl]-3h-benzimidazole-5-carboxamide Chemical compound COC1=CC(C)=CC=C1OC1=CC=C(C=2NC3=CC=C(C=C3N=2)C(N)=O)C=C1Cl GCKIINJXIXPHKJ-UHFFFAOYSA-N 0.000 claims description 3
• XMZUWWYINMWAGW-UHFFFAOYSA-N 2-[3-chloro-4-(3,4-dimethoxyphenoxy)phenyl]-3h-benzimidazole-5-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1OC1=CC=C(C=2NC3=CC=C(C=C3N=2)C(N)=O)C=C1Cl XMZUWWYINMWAGW-UHFFFAOYSA-N 0.000 claims description 3
• BYAONKUTDKSCTA-UHFFFAOYSA-N 2-[3-chloro-4-(3-chloro-4-methylphenoxy)phenyl]-3h-benzimidazole-5-carboxamide Chemical compound C1=C(Cl)C(C)=CC=C1OC1=CC=C(C=2NC3=CC=C(C=C3N=2)C(N)=O)C=C1Cl BYAONKUTDKSCTA-UHFFFAOYSA-N 0.000 claims description 3
• FHQUCUVXNXLUMV-UHFFFAOYSA-N 2-[3-chloro-4-(4-fluoro-3-methylphenoxy)phenyl]-3h-benzimidazole-5-carboxamide Chemical compound C1=C(F)C(C)=CC(OC=2C(=CC(=CC=2)C=2NC3=CC=C(C=C3N=2)C(N)=O)Cl)=C1 FHQUCUVXNXLUMV-UHFFFAOYSA-N 0.000 claims description 3
• NWSGQGNPAITUCX-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenoxy)phenyl]-3h-benzimidazole-5-carboxamide Chemical compound N=1C2=CC(C(=O)N)=CC=C2NC=1C(C=C1)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 NWSGQGNPAITUCX-UHFFFAOYSA-N 0.000 claims description 3
• TXGLUOQCFZQLHG-UHFFFAOYSA-N 2-[4-(3-chloro-4-fluorophenoxy)phenyl]-3h-benzimidazole-5-carboxamide Chemical compound N=1C2=CC(C(=O)N)=CC=C2NC=1C(C=C1)=CC=C1OC1=CC=C(F)C(Cl)=C1 TXGLUOQCFZQLHG-UHFFFAOYSA-N 0.000 claims description 3
• FXHGEANNJJDHMK-UHFFFAOYSA-N 2-[4-(3-chloro-4-fluorophenyl)sulfanylphenyl]-3h-benzimidazole-5-carboxamide Chemical compound N=1C2=CC(C(=O)N)=CC=C2NC=1C(C=C1)=CC=C1SC1=CC=C(F)C(Cl)=C1 FXHGEANNJJDHMK-UHFFFAOYSA-N 0.000 claims description 3
• PKIQLNKKGMPCHK-UHFFFAOYSA-N 2-[4-(3-chloro-4-fluorophenyl)sulfanylphenyl]-3h-benzimidazole-5-sulfonamide Chemical compound N=1C2=CC(S(=O)(=O)N)=CC=C2NC=1C(C=C1)=CC=C1SC1=CC=C(F)C(Cl)=C1 PKIQLNKKGMPCHK-UHFFFAOYSA-N 0.000 claims description 3
• OWOPCMLGEOLRDH-UHFFFAOYSA-N 2-[4-(3-chloro-4-methylphenoxy)phenyl]-3h-benzimidazole-5-carboxamide Chemical compound C1=C(Cl)C(C)=CC=C1OC1=CC=C(C=2NC3=CC=C(C=C3N=2)C(N)=O)C=C1 OWOPCMLGEOLRDH-UHFFFAOYSA-N 0.000 claims description 3
• BDWGIUYERCLROD-UHFFFAOYSA-N 2-[4-(3-methoxyphenyl)sulfanylphenyl]-3h-benzimidazole-5-carboxamide Chemical compound COC1=CC=CC(SC=2C=CC(=CC=2)C=2NC3=CC=C(C=C3N=2)C(N)=O)=C1 BDWGIUYERCLROD-UHFFFAOYSA-N 0.000 claims description 3
• DQFBXMPFRTWEOC-UHFFFAOYSA-N 2-[4-(4-chloro-2-hydroxyphenoxy)phenyl]-3h-benzimidazole-5-carboxamide Chemical compound N=1C2=CC(C(=O)N)=CC=C2NC=1C(C=C1)=CC=C1OC1=CC=C(Cl)C=C1O DQFBXMPFRTWEOC-UHFFFAOYSA-N 0.000 claims description 3
• WFJNFYDWAZXCIJ-UHFFFAOYSA-N 2-[4-(4-chloro-3-fluorophenoxy)phenyl]-3h-benzimidazole-5-carboxamide Chemical compound N=1C2=CC(C(=O)N)=CC=C2NC=1C(C=C1)=CC=C1OC1=CC=C(Cl)C(F)=C1 WFJNFYDWAZXCIJ-UHFFFAOYSA-N 0.000 claims description 3
• RQKQQACLXABERV-UHFFFAOYSA-N 2-[4-(4-chloro-3-hydroxyphenoxy)phenyl]-3h-benzimidazole-5-carboxamide Chemical compound N=1C2=CC(C(=O)N)=CC=C2NC=1C(C=C1)=CC=C1OC1=CC=C(Cl)C(O)=C1 RQKQQACLXABERV-UHFFFAOYSA-N 0.000 claims description 3
• JKCDNKQAKWXQNO-UHFFFAOYSA-N 2-[4-(4-chlorophenoxy)phenyl]-1h-imidazo[4,5-b]pyridine-5-carboxamide Chemical compound N=1C2=NC(C(=O)N)=CC=C2NC=1C(C=C1)=CC=C1OC1=CC=C(Cl)C=C1 JKCDNKQAKWXQNO-UHFFFAOYSA-N 0.000 claims description 3
• XCCULJHTWCXXQM-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)sulfonylphenyl]-3h-benzimidazole-5-carboxamide Chemical compound N=1C2=CC(C(=O)N)=CC=C2NC=1C(C=C1)=CC=C1S(=O)(=O)C1=CC=C(Cl)C=C1 XCCULJHTWCXXQM-UHFFFAOYSA-N 0.000 claims description 3
• VBIMRSFMRWSBEL-UHFFFAOYSA-N 2-[4-(4-ethylphenyl)sulfanylphenyl]-3h-benzimidazole-5-carboxamide Chemical compound C1=CC(CC)=CC=C1SC1=CC=C(C=2NC3=CC=C(C=C3N=2)C(N)=O)C=C1 VBIMRSFMRWSBEL-UHFFFAOYSA-N 0.000 claims description 3
• OBGAXPZOBLEYIK-UHFFFAOYSA-N 2-[4-(4-iodophenoxy)phenyl]-3h-benzimidazole-5-carboxamide Chemical compound N=1C2=CC(C(=O)N)=CC=C2NC=1C(C=C1)=CC=C1OC1=CC=C(I)C=C1 OBGAXPZOBLEYIK-UHFFFAOYSA-N 0.000 claims description 3
• GAEMJVIRBHBIAF-UHFFFAOYSA-N 2-[4-(4-pyridin-2-ylpiperazin-1-yl)phenyl]-3h-benzimidazole-5-carboxamide Chemical compound N=1C2=CC(C(=O)N)=CC=C2NC=1C(C=C1)=CC=C1N(CC1)CCN1C1=CC=CC=N1 GAEMJVIRBHBIAF-UHFFFAOYSA-N 0.000 claims description 3
• NDFFIDXWQGDNAR-UHFFFAOYSA-N 2-[4-(naphthalen-2-ylsulfamoyl)phenyl]-3h-benzimidazole-5-carboxamide Chemical compound C1=CC=CC2=CC(NS(=O)(=O)C3=CC=C(C=C3)C=3NC4=CC=C(C=C4N=3)C(=O)N)=CC=C21 NDFFIDXWQGDNAR-UHFFFAOYSA-N 0.000 claims description 3
• ZMHFEOJMVKVVDH-UHFFFAOYSA-N 2-[4-[(2,4-dichlorophenyl)sulfamoyl]phenyl]-3h-benzimidazole-5-carboxamide Chemical compound N=1C2=CC(C(=O)N)=CC=C2NC=1C(C=C1)=CC=C1S(=O)(=O)NC1=CC=C(Cl)C=C1Cl ZMHFEOJMVKVVDH-UHFFFAOYSA-N 0.000 claims description 3
• GWOSBFWKYVPXEI-UHFFFAOYSA-N 2-[4-[(4-bromophenyl)sulfamoyl]phenyl]-3h-benzimidazole-5-carboxamide Chemical compound N=1C2=CC(C(=O)N)=CC=C2NC=1C(C=C1)=CC=C1S(=O)(=O)NC1=CC=C(Br)C=C1 GWOSBFWKYVPXEI-UHFFFAOYSA-N 0.000 claims description 3
• CVGVSWYXRODYIS-UHFFFAOYSA-N 2-[4-[(4-chlorophenyl)-methylcarbamoyl]phenyl]-3h-benzimidazole-5-carboxamide Chemical compound C=1C=C(C=2NC3=CC=C(C=C3N=2)C(N)=O)C=CC=1C(=O)N(C)C1=CC=C(Cl)C=C1 CVGVSWYXRODYIS-UHFFFAOYSA-N 0.000 claims description 3
• JUMNXHYLVIXBOA-UHFFFAOYSA-N 2-[4-[(4-chlorophenyl)-methylsulfamoyl]phenyl]-3h-benzimidazole-5-carboxamide Chemical compound C=1C=C(C=2NC3=CC=C(C=C3N=2)C(N)=O)C=CC=1S(=O)(=O)N(C)C1=CC=C(Cl)C=C1 JUMNXHYLVIXBOA-UHFFFAOYSA-N 0.000 claims description 3
• QEMULFAUDKUPNT-UHFFFAOYSA-N 2-[4-[(4-chlorophenyl)carbamoyl]phenyl]-3h-benzimidazole-5-carboxamide Chemical compound N=1C2=CC(C(=O)N)=CC=C2NC=1C(C=C1)=CC=C1C(=O)NC1=CC=C(Cl)C=C1 QEMULFAUDKUPNT-UHFFFAOYSA-N 0.000 claims description 3
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