CA2464000C - 2-phenyl benzimidazoles and imidazo-[4,5]-pyridines as cdsi/chk2-inhibitors and adjuvants to chemotherapy or radiation therapy in the treatment of cancer - Google Patents

Info

Publication number

CA2464000C

CA2464000C CA2464000A CA2464000A CA2464000C CA 2464000 C CA2464000 C CA 2464000C CA 2464000 A CA2464000 A CA 2464000A CA 2464000 A CA2464000 A CA 2464000A CA 2464000 C CA2464000 C CA 2464000C

Authority

CA

Canada

Prior art keywords

phenyl

chloro

benzoimidazole

carboxylic acid

acid amide

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 58
• 201000011510 cancer Diseases 0.000 title claims abstract description 39
• 238000011282 treatment Methods 0.000 title claims abstract description 36
• 239000002671 adjuvant Substances 0.000 title abstract description 17
• 239000003112 inhibitor Substances 0.000 title abstract description 6
• GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical class C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 title abstract description 3
• 238000002512 chemotherapy Methods 0.000 title abstract description 3
• 238000001959 radiotherapy Methods 0.000 title abstract description 3
• DWYHDSLIWMUSOO-UHFFFAOYSA-N 2-phenyl-1h-benzimidazole Chemical class C1=CC=CC=C1C1=NC2=CC=CC=C2N1 DWYHDSLIWMUSOO-UHFFFAOYSA-N 0.000 title 1
• -1 piperazin-diyl Chemical group 0.000 claims abstract description 247
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 38
• 125000003118 aryl group Chemical group 0.000 claims abstract description 29
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 20
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 17
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 16
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 13
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
• 239000001257 hydrogen Substances 0.000 claims abstract description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
• 150000002367 halogens Chemical class 0.000 claims abstract description 5
• 125000000520 N-substituted aminocarbonyl group Chemical group [*]NC(=O)* 0.000 claims abstract description 4
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 15
• 101150009274 nhr-1 gene Proteins 0.000 claims abstract 6
• 125000001475 halogen functional group Chemical group 0.000 claims abstract 5
• 150000001875 compounds Chemical class 0.000 claims description 224
• 229910052799 carbon Inorganic materials 0.000 claims description 41
• 150000001721 carbon Chemical group 0.000 claims description 32
• 125000004432 carbon atom Chemical group C* 0.000 claims description 31
• 229910052740 iodine Inorganic materials 0.000 claims description 29
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 18
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
• 150000001408 amides Chemical class 0.000 claims description 17
• 239000003795 chemical substances by application Substances 0.000 claims description 16
• 150000003839 salts Chemical class 0.000 claims description 16
• 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 15
• 125000002950 monocyclic group Chemical group 0.000 claims description 15
• 125000004076 pyridyl group Chemical group 0.000 claims description 14
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
• 125000001246 bromo group Chemical group Br* 0.000 claims description 11
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 11
• 150000002148 esters Chemical class 0.000 claims description 11
• 125000002541 furyl group Chemical group 0.000 claims description 11
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 11
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 10
• 125000001544 thienyl group Chemical group 0.000 claims description 10
• 230000000254 damaging effect Effects 0.000 claims description 9
• JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 claims description 9
• 125000002883 imidazolyl group Chemical group 0.000 claims description 8
• 125000001424 substituent group Chemical group 0.000 claims description 8
• 125000000335 thiazolyl group Chemical group 0.000 claims description 8
• 229910052801 chlorine Inorganic materials 0.000 claims description 7
• 229910052731 fluorine Inorganic materials 0.000 claims description 7
• 125000001183 hydrocarbyl group 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
• 238000002360 preparation method Methods 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
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 6
• 229910006074 SO2NH2 Inorganic materials 0.000 claims description 6
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 6
• 239000003814 drug Substances 0.000 claims description 6
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 5
• CARBLJDZRGDDSV-UHFFFAOYSA-N 2-[3-chloro-4-[(4-chlorophenyl)sulfamoyl]phenyl]-3h-benzimidazole-5-carboxamide Chemical compound N1C2=CC(C(=O)N)=CC=C2N=C1C(C=C1Cl)=CC=C1S(=O)(=O)NC1=CC=C(Cl)C=C1 CARBLJDZRGDDSV-UHFFFAOYSA-N 0.000 claims description 4
• KFEQHDDFRVVFGF-UHFFFAOYSA-N 2-[4-(4-chloro-3-sulfamoylphenoxy)phenyl]-3h-benzimidazole-5-carboxamide Chemical compound N1C2=CC(C(=O)N)=CC=C2N=C1C(C=C1)=CC=C1OC1=CC=C(Cl)C(S(N)(=O)=O)=C1 KFEQHDDFRVVFGF-UHFFFAOYSA-N 0.000 claims description 4
• UMJSUXPOBMBISY-UHFFFAOYSA-N 2-[4-(4-chloroanilino)phenyl]-3h-benzimidazole-5-carboxamide Chemical compound N1C2=CC(C(=O)N)=CC=C2N=C1C(C=C1)=CC=C1NC1=CC=C(Cl)C=C1 UMJSUXPOBMBISY-UHFFFAOYSA-N 0.000 claims description 4
• UFINQTABZSAHAA-UHFFFAOYSA-N 2-[4-[4-chloro-3-(dimethylamino)phenoxy]phenyl]-3h-benzimidazole-5-carboxamide Chemical compound C1=C(Cl)C(N(C)C)=CC(OC=2C=CC(=CC=2)C=2NC3=CC(=CC=C3N=2)C(N)=O)=C1 UFINQTABZSAHAA-UHFFFAOYSA-N 0.000 claims description 4
• QSATYODVTPXBHQ-UHFFFAOYSA-N 2-[4-[4-chloro-3-(methanesulfonamido)phenoxy]phenyl]-3h-benzimidazole-5-carboxamide Chemical compound C1=C(Cl)C(NS(=O)(=O)C)=CC(OC=2C=CC(=CC=2)C=2NC3=CC(=CC=C3N=2)C(N)=O)=C1 QSATYODVTPXBHQ-UHFFFAOYSA-N 0.000 claims description 4
• WZAQGBNGGLBNHX-UHFFFAOYSA-N 2-[6-[(2,4-dichlorophenyl)sulfamoyl]pyridin-3-yl]-3h-benzimidazole-5-carboxamide Chemical compound N1C2=CC(C(=O)N)=CC=C2N=C1C(C=N1)=CC=C1S(=O)(=O)NC1=CC=C(Cl)C=C1Cl WZAQGBNGGLBNHX-UHFFFAOYSA-N 0.000 claims description 4
• QHGFZMGCLAYOHF-UHFFFAOYSA-N 2-[6-[(3,4-dichlorophenyl)sulfamoyl]pyridin-3-yl]-3h-benzimidazole-5-carboxamide Chemical compound N1C2=CC(C(=O)N)=CC=C2N=C1C(C=N1)=CC=C1S(=O)(=O)NC1=CC=C(Cl)C(Cl)=C1 QHGFZMGCLAYOHF-UHFFFAOYSA-N 0.000 claims description 4
• BVGJBRNVONUDJY-UHFFFAOYSA-N 2-[6-[(4-chlorophenyl)sulfamoyl]pyridin-3-yl]-3h-benzimidazole-5-carboxamide Chemical compound N1C2=CC(C(=O)N)=CC=C2N=C1C(C=N1)=CC=C1S(=O)(=O)NC1=CC=C(Cl)C=C1 BVGJBRNVONUDJY-UHFFFAOYSA-N 0.000 claims description 4
• XSOGJFDKBPOUFB-UHFFFAOYSA-N 2-[6-[(4-chlorophenyl)sulfonylamino]pyridin-3-yl]-3h-benzimidazole-5-carboxamide Chemical compound N1C2=CC(C(=O)N)=CC=C2N=C1C(C=N1)=CC=C1NS(=O)(=O)C1=CC=C(Cl)C=C1 XSOGJFDKBPOUFB-UHFFFAOYSA-N 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
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 4
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
• 125000001624 naphthyl group Chemical group 0.000 claims description 4
• 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 4
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 3
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 3
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 3
• 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 3
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 3
• 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 3
• 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims description 3
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
• 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 claims description 3
• 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 3
• 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 3
• UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 3
• 125000004245 indazol-3-yl group Chemical group [H]N1N=C(*)C2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 3
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 3
• 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 3
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
• 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 3
• 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 3
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
• 125000004258 purin-2-yl group Chemical group [H]N1C2=NC(*)=NC([H])=C2N([H])C1([H])[H] 0.000 claims description 3
• 125000004544 purin-8-yl group Chemical group N1=CN=C2N=C(NC2=C1)* 0.000 claims description 3
• 125000004571 thiomorpholin-4-yl group Chemical group N1(CCSCC1)* 0.000 claims description 3
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 6
• QYWJVCPTPQEBQA-UHFFFAOYSA-N 2-[6-(4-chlorophenoxy)pyridazin-3-yl]-3h-benzimidazole-5-carboxamide Chemical compound N1C2=CC(C(=O)N)=CC=C2N=C1C(N=N1)=CC=C1OC1=CC=C(Cl)C=C1 QYWJVCPTPQEBQA-UHFFFAOYSA-N 0.000 claims 3
• 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 2
• 125000001931 aliphatic group Chemical group 0.000 claims 2
• 125000000565 sulfonamide group Chemical group 0.000 claims 1
• 150000001556 benzimidazoles Chemical class 0.000 abstract description 9
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• 101150095530 CDS1 gene Proteins 0.000 abstract description 3
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• 238000000034 method Methods 0.000 description 124
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