AU2004238497B2 - Benzimidazole-derivatives as factor Xa inhibitors - Google Patents

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Publication number

AU2004238497B2

AU2004238497B2 AU2004238497A AU2004238497A AU2004238497B2 AU 2004238497 B2 AU2004238497 B2 AU 2004238497B2 AU 2004238497 A AU2004238497 A AU 2004238497A AU 2004238497 A AU2004238497 A AU 2004238497A AU 2004238497 B2 AU2004238497 B2 AU 2004238497B2

Authority

AU

Australia

Prior art keywords

chloro

benzoimidazole

ylcarbamoyl

carboxylic acid

piperidin

Prior art date

2003-05-19

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 - Fee Related

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• 229940123583 Factor Xa inhibitor Drugs 0.000 title description 2
• 229940058303 antinematodal benzimidazole derivative Drugs 0.000 title description 2
• -1 phenylpyridyl Chemical group 0.000 claims description 444
• 150000001875 compounds Chemical class 0.000 claims description 235
• 239000000203 mixture Substances 0.000 claims description 140
• 125000000623 heterocyclic group Chemical group 0.000 claims description 105
• 125000000217 alkyl group Chemical group 0.000 claims description 74
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 74
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 63
• 125000003118 aryl group Chemical group 0.000 claims description 62
• 229910052757 nitrogen Inorganic materials 0.000 claims description 48
• 229910052736 halogen Inorganic materials 0.000 claims description 46
• 150000002367 halogens Chemical class 0.000 claims description 44
• 150000003839 salts Chemical class 0.000 claims description 44
• 229910052739 hydrogen Inorganic materials 0.000 claims description 43
• 125000004122 cyclic group Chemical group 0.000 claims description 41
• 239000001257 hydrogen Substances 0.000 claims description 38
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 37
• 125000002950 monocyclic group Chemical group 0.000 claims description 37
• 125000005842 heteroatom Chemical group 0.000 claims description 36
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 32
• 125000002619 bicyclic group Chemical group 0.000 claims description 32
• 229910052760 oxygen Inorganic materials 0.000 claims description 32
• 125000004076 pyridyl group Chemical group 0.000 claims description 32
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 31
• 239000001301 oxygen Substances 0.000 claims description 31
• 125000001544 thienyl group Chemical group 0.000 claims description 30
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 29
• 239000002253 acid Substances 0.000 claims description 28
• 239000000460 chlorine Substances 0.000 claims description 25
• YTZLTDSMHZMVDQ-UHFFFAOYSA-N n-(1-propan-2-ylpiperidin-4-yl)-1h-benzimidazole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=CC=CC=C2N1 YTZLTDSMHZMVDQ-UHFFFAOYSA-N 0.000 claims description 25
• 229920006395 saturated elastomer Polymers 0.000 claims description 25
• FGSITYJTOINIBZ-UHFFFAOYSA-N methyl 3-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]-6-(2,2,2-trifluoroethoxy)thieno[3,4-d]imidazole-4-carboxylate Chemical compound C1=C(C=2SC(Cl)=CC=2)ON=C1CN1C2=C(C(=O)OC)SC(OCC(F)(F)F)=C2N=C1C(=O)NC1CCN(C(C)C)CC1 FGSITYJTOINIBZ-UHFFFAOYSA-N 0.000 claims description 24
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 21
• FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims description 20
• RHXSYTACTOMVLJ-UHFFFAOYSA-N 1H-benzimidazole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=NC2=C1 RHXSYTACTOMVLJ-UHFFFAOYSA-N 0.000 claims description 20
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
• 229910052717 sulfur Inorganic materials 0.000 claims description 20
• 239000011593 sulfur Substances 0.000 claims description 20
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 19
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 19
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 19
• 125000000335 thiazolyl group Chemical group 0.000 claims description 19
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 18
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 18
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 17
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 17
• 125000002971 oxazolyl group Chemical group 0.000 claims description 17
• 150000001408 amides Chemical class 0.000 claims description 16
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 16
• 125000002883 imidazolyl group Chemical group 0.000 claims description 16
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 15
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 15
• 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 15
• 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 15
• 125000001041 indolyl group Chemical group 0.000 claims description 15
• 125000003384 isochromanyl group Chemical group C1(OCCC2=CC=CC=C12)* 0.000 claims description 15
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 15
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 15
• 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 15
• 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 15
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 15
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 15
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 14
• 125000002541 furyl group Chemical group 0.000 claims description 14
• 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 14
• 125000002053 thietanyl group Chemical group 0.000 claims description 14
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 13
• NVKJJNQVQGPXLK-UHFFFAOYSA-N 3-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]benzimidazole-5-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=CC=C(C(O)=O)C=C2N1CC(=O)NC1=CC=C(Cl)C=N1 NVKJJNQVQGPXLK-UHFFFAOYSA-N 0.000 claims description 13
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 13
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 13
• OTJKNFNMTJVBBI-UHFFFAOYSA-N 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]benzimidazole-4-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=C(C(O)=O)C=CC=C2N1CC(=O)NC1=CC=C(Cl)C=N1 OTJKNFNMTJVBBI-UHFFFAOYSA-N 0.000 claims description 12
• 125000004429 atom Chemical group 0.000 claims description 12
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 12
• 125000004432 carbon atom Chemical group C* 0.000 claims description 10
• 125000003386 piperidinyl group Chemical group 0.000 claims description 10
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 10
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 10
• 125000005955 1H-indazolyl group Chemical group 0.000 claims description 9
• 125000003971 isoxazolinyl group Chemical group 0.000 claims description 9
• 125000002757 morpholinyl group Chemical group 0.000 claims description 9
• 125000004193 piperazinyl group Chemical group 0.000 claims description 9
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 9
• 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 8
• OTHZUYXCXAQVKE-UHFFFAOYSA-N 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]benzimidazole-5-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=CC(C(O)=O)=CC=C2N1CC(=O)NC1=CC=C(Cl)C=N1 OTHZUYXCXAQVKE-UHFFFAOYSA-N 0.000 claims description 8
• IRJWDLCUWPWEKJ-UHFFFAOYSA-N 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]benzimidazole-2,5-dicarboxylic acid Chemical compound OC(=O)C1=NC2=CC(C(O)=O)=CC=C2N1CC(=O)NC1=CC=C(Cl)C=N1 IRJWDLCUWPWEKJ-UHFFFAOYSA-N 0.000 claims description 8
• 125000005602 azabenzimidazolyl group Chemical group 0.000 claims description 8
• 150000002431 hydrogen Chemical class 0.000 claims description 8
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 8
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 8
• 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 claims description 7
• 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 claims description 7
• 125000004529 1,2,3-triazinyl group Chemical group N1=NN=C(C=C1)* 0.000 claims description 7
• 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims description 7
• 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 7
• 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims description 7
• 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims description 7
• JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 claims description 7
• 125000005962 1,4-oxazepanyl group Chemical group 0.000 claims description 7
• 125000000183 1,4-thiazinyl group Chemical group S1C(C=NC=C1)* 0.000 claims description 7
• OKUVXXZKJBEARR-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]benzimidazole-4-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=C(C(O)=O)C=CC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 OKUVXXZKJBEARR-UHFFFAOYSA-N 0.000 claims description 7
• ZRQQXFMGYSOKDF-UHFFFAOYSA-N 1-propan-2-ylpiperidin-4-amine Chemical compound CC(C)N1CCC(N)CC1 ZRQQXFMGYSOKDF-UHFFFAOYSA-N 0.000 claims description 7
• MDDWTXJTGBXKJS-UHFFFAOYSA-N 3-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]benzimidazole-2,5-dicarboxylic acid Chemical compound OC(=O)C1=NC2=CC=C(C(O)=O)C=C2N1CC(=O)NC1=CC=C(Cl)C=N1 MDDWTXJTGBXKJS-UHFFFAOYSA-N 0.000 claims description 7
• 125000002471 4H-quinolizinyl group Chemical group C=1(C=CCN2C=CC=CC12)* 0.000 claims description 7
• OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 7
• 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 7
• 125000002785 azepinyl group Chemical group 0.000 claims description 7
• 125000002393 azetidinyl group Chemical group 0.000 claims description 7
• 125000004069 aziridinyl group Chemical group 0.000 claims description 7
• 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 7
• 125000005512 benztetrazolyl group Chemical group 0.000 claims description 7
• 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 7
• 125000004623 carbolinyl group Chemical group 0.000 claims description 7
• 229910052799 carbon Inorganic materials 0.000 claims description 7
• 125000003838 furazanyl group Chemical group 0.000 claims description 7
• 125000002632 imidazolidinyl group Chemical group 0.000 claims description 7
• 125000002636 imidazolinyl group Chemical group 0.000 claims description 7
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 7
• 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 7
• 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 claims description 7
• 125000005438 isoindazolyl group Chemical group 0.000 claims description 7
• 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims description 7
• 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 claims description 7
• 125000005969 isothiazolinyl group Chemical group 0.000 claims description 7
• 125000003965 isoxazolidinyl group Chemical group 0.000 claims description 7
• 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 7
• 125000004930 octahydroisoquinolinyl group Chemical group C1(NCCC2CCCC=C12)* 0.000 claims description 7
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 7
• 125000000160 oxazolidinyl group Chemical group 0.000 claims description 7
• 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 claims description 7
• 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 claims description 7
• 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims description 7
• 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 7
• 125000005954 phenoxathiinyl group Chemical group 0.000 claims description 7
• 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 claims description 7
• 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 7
• 125000003072 pyrazolidinyl group Chemical group 0.000 claims description 7
• 125000002755 pyrazolinyl group Chemical group 0.000 claims description 7
• 125000001422 pyrrolinyl group Chemical group 0.000 claims description 7
• 125000003507 tetrahydrothiofenyl group Chemical group 0.000 claims description 7
• 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 claims description 7
• 125000004627 thianthrenyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3SC12)* 0.000 claims description 7
• 125000001984 thiazolidinyl group Chemical group 0.000 claims description 7
• 125000002769 thiazolinyl group Chemical group 0.000 claims description 7
• 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 claims description 7
• 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 claims description 6
• 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 claims description 6
• 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims description 6
• 125000000164 1,3-thiazinyl group Chemical group S1C(N=CC=C1)* 0.000 claims description 6
• VMDMDXBHVFLFLL-UHFFFAOYSA-N 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]benzimidazole-2,4-dicarboxylic acid Chemical compound OC(=O)C1=NC2=C(C(O)=O)C=CC=C2N1CC(=O)NC1=CC=C(Cl)C=N1 VMDMDXBHVFLFLL-UHFFFAOYSA-N 0.000 claims description 6
• FZICQKXJQSAKIP-UHFFFAOYSA-N 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]benzimidazole-2-carboxylic acid Chemical compound OC(=O)C1=NC2=CC=CC=C2N1CC(=O)NC1=CC=C(Cl)C=N1 FZICQKXJQSAKIP-UHFFFAOYSA-N 0.000 claims description 6
• BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 6
• 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims description 6
• 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 claims description 6
• 125000005968 oxazolinyl group Chemical group 0.000 claims description 6
• 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 claims description 6
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
• AGESFIMXCRGLKV-UHFFFAOYSA-N 1-(4-aminophenyl)pyrazin-2-one Chemical compound C1=CC(N)=CC=C1N1C(=O)C=NC=C1 AGESFIMXCRGLKV-UHFFFAOYSA-N 0.000 claims description 5
• UXHBTHAUDXFENU-UHFFFAOYSA-N 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-4-(2-ethoxyethoxy)-n-(1-propan-2-ylpiperidin-4-yl)benzimidazole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC=2C(OCCOCC)=CC=CC=2N1CC(=O)NC1=CC=C(Cl)C=N1 UXHBTHAUDXFENU-UHFFFAOYSA-N 0.000 claims description 5
• WBMYIGWEQSJQAH-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]benzimidazole-2,4-dicarboxylic acid Chemical compound OC(=O)C1=NC2=C(C(O)=O)C=CC=C2N1CC(=NO1)C=C1C1=CC=C(Cl)S1 WBMYIGWEQSJQAH-UHFFFAOYSA-N 0.000 claims description 5
• SVYISQCXXAWMJM-UHFFFAOYSA-N 3-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(1-propan-2-ylpiperidin-4-yl)imidazo[4,5-b]pyridine-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=CC=CN=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 SVYISQCXXAWMJM-UHFFFAOYSA-N 0.000 claims description 5
• 125000005493 quinolyl group Chemical group 0.000 claims description 5
• 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims description 5
• YCMIKXOUACICIK-UHFFFAOYSA-N 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-5-(2-hydroxyethylsulfonyl)-n-(1-propan-2-ylpiperidin-4-yl)benzimidazole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=CC(S(=O)(=O)CCO)=CC=C2N1CC(=O)NC1=CC=C(Cl)C=N1 YCMIKXOUACICIK-UHFFFAOYSA-N 0.000 claims description 4
• ADTRLMBWHNHJAQ-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,3,4-thiadiazol-2-yl]methyl]-2-[(1-cyclopropylpiperidin-4-yl)carbamoyl]benzimidazole-5-carboxylic acid Chemical compound C1CN(C2CC2)CCC1NC(=O)C1=NC2=CC(C(=O)O)=CC=C2N1CC(S1)=NN=C1C1=CC=C(Cl)S1 ADTRLMBWHNHJAQ-UHFFFAOYSA-N 0.000 claims description 4
• XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical compound C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 claims description 4
• WLSXXQHRDUZVRE-UHFFFAOYSA-N 3-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]thieno[3,4-d]imidazole-4-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=CSC(C(O)=O)=C2N1CC(=O)NC1=CC=C(Cl)C=N1 WLSXXQHRDUZVRE-UHFFFAOYSA-N 0.000 claims description 4
• OGLDWMOFWSCFEX-UHFFFAOYSA-N 3-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-6-(1,4-oxazepane-4-carbonyl)-n-(1-propan-2-ylpiperidin-4-yl)thieno[3,4-d]imidazole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=C(C(=O)N3CCOCCC3)SC=C2N1CC(=O)NC1=CC=C(Cl)C=N1 OGLDWMOFWSCFEX-UHFFFAOYSA-N 0.000 claims description 4
• HUXHMUUXTATWJQ-UHFFFAOYSA-N methyl 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]benzimidazole-4-carboxylate Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC=2C(C(=O)OC)=CC=CC=2N1CC(=O)NC1=CC=C(Cl)C=N1 HUXHMUUXTATWJQ-UHFFFAOYSA-N 0.000 claims description 4
• MQDJLSCBTJGRKB-UHFFFAOYSA-N methyl 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-2-[(1-cyclopropylpiperidin-4-yl)carbamoyl]benzimidazole-5-carboxylate Chemical compound C1CN(C2CC2)CCC1NC(=O)C1=NC2=CC(C(=O)OC)=CC=C2N1CC(=NO1)C=C1C1=CC=C(Cl)S1 MQDJLSCBTJGRKB-UHFFFAOYSA-N 0.000 claims description 4
• 125000005880 oxathiolanyl group Chemical group 0.000 claims description 4
• SRTGZXSRGMPOHI-UHFFFAOYSA-N 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-2-[(1-cyclopropylpiperidin-4-yl)carbamoyl]benzimidazole-4-carboxylic acid Chemical compound C1CN(C2CC2)CCC1NC(=O)C1=NC=2C(C(=O)O)=CC=CC=2N1CC(=O)NC1=CC=C(Cl)C=N1 SRTGZXSRGMPOHI-UHFFFAOYSA-N 0.000 claims description 3
• USHKKKQCKYHKPT-UHFFFAOYSA-N 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-2-[[4-(3-oxomorpholin-4-yl)phenyl]carbamoyl]benzimidazole-4-carboxylic acid Chemical compound C=1C=C(N2C(COCC2)=O)C=CC=1NC(=O)C1=NC=2C(C(=O)O)=CC=CC=2N1CC(=O)NC1=CC=C(Cl)C=N1 USHKKKQCKYHKPT-UHFFFAOYSA-N 0.000 claims description 3
• WKRRPVLJSBWLCS-UHFFFAOYSA-N 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-4-(2-methoxyethoxy)-n-(1-propan-2-ylpiperidin-4-yl)benzimidazole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC=2C(OCCOC)=CC=CC=2N1CC(=O)NC1=CC=C(Cl)C=N1 WKRRPVLJSBWLCS-UHFFFAOYSA-N 0.000 claims description 3
• SBYMGTMVNILPJE-UHFFFAOYSA-N 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-4-(2-methoxyethoxy)-n-[4-(3-oxomorpholin-4-yl)phenyl]benzimidazole-2-carboxamide Chemical compound C=1C=C(N2C(COCC2)=O)C=CC=1NC(=O)C1=NC=2C(OCCOC)=CC=CC=2N1CC(=O)NC1=CC=C(Cl)C=N1 SBYMGTMVNILPJE-UHFFFAOYSA-N 0.000 claims description 3
• ALNMAWGOKNHARU-UHFFFAOYSA-N 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-6-(2-hydroxyethylsulfonyl)-n-(1-propan-2-ylpiperidin-4-yl)benzimidazole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=CC=C(S(=O)(=O)CCO)C=C2N1CC(=O)NC1=CC=C(Cl)C=N1 ALNMAWGOKNHARU-UHFFFAOYSA-N 0.000 claims description 3
• FRPAEZVDMHBCFI-UHFFFAOYSA-N 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-n-[4-(3-oxomorpholin-4-yl)phenyl]benzimidazole-2-carboxamide Chemical compound N1=CC(Cl)=CC=C1NC(=O)CN1C2=CC=CC=C2N=C1C(=O)NC1=CC=C(N2C(COCC2)=O)C=C1 FRPAEZVDMHBCFI-UHFFFAOYSA-N 0.000 claims description 3
• YLVDHNSFFZKYPB-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-2-[(1-cyclopropylpiperidin-4-yl)carbamoyl]benzimidazole-4-carboxylic acid Chemical compound C1CN(C2CC2)CCC1NC(=O)C1=NC=2C(C(=O)O)=CC=CC=2N1CC(=NO1)C=C1C1=CC=C(Cl)S1 YLVDHNSFFZKYPB-UHFFFAOYSA-N 0.000 claims description 3
• IMFFMUPJZJSIAL-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]benzimidazole-5-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=CC(C(O)=O)=CC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 IMFFMUPJZJSIAL-UHFFFAOYSA-N 0.000 claims description 3
• QQPMMTIDTMKOGP-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-4-(3-hydroxyazetidine-1-carbonyl)-n-(1-propan-2-ylpiperidin-4-yl)benzimidazole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=C(C(=O)N3CC(O)C3)C=CC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 QQPMMTIDTMKOGP-UHFFFAOYSA-N 0.000 claims description 3
• XGFZEONRZIUFGI-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(1-propan-2-ylpiperidin-4-yl)benzimidazole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=CC=CC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 XGFZEONRZIUFGI-UHFFFAOYSA-N 0.000 claims description 3
• SIHSPDKPDZJEHR-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(1-pyrimidin-4-ylpiperidin-4-yl)benzimidazole-2-carboxamide Chemical compound S1C(Cl)=CC=C1C1=CC(CN2C3=CC=CC=C3N=C2C(=O)NC2CCN(CC2)C=2N=CN=CC=2)=NO1 SIHSPDKPDZJEHR-UHFFFAOYSA-N 0.000 claims description 3
• AWAFQKCSARQPCL-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]benzimidazole-2,5-dicarboxylic acid Chemical compound OC(=O)C1=NC2=CC(C(O)=O)=CC=C2N1CC(=NO1)C=C1C1=CC=C(Cl)S1 AWAFQKCSARQPCL-UHFFFAOYSA-N 0.000 claims description 3
• UWZJASBOGIDCPX-UHFFFAOYSA-N 3-[[3-(5-chlorothiophen-2-yl)-1,2-oxazol-5-yl]methyl]-2-[(1-cyclopropylpiperidin-4-yl)carbamoyl]benzimidazole-5-carboxylic acid Chemical compound C=1C(C=2SC(Cl)=CC=2)=NOC=1CN1C2=CC(C(=O)O)=CC=C2N=C1C(=O)NC(CC1)CCN1C1CC1 UWZJASBOGIDCPX-UHFFFAOYSA-N 0.000 claims description 3
• JZVCZVTVKDLABR-UHFFFAOYSA-N 3-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-2-[(1-cyclopropylpiperidin-4-yl)carbamoyl]thieno[3,4-d]imidazole-4-carboxylic acid Chemical compound C1=C(C=2SC(Cl)=CC=2)ON=C1CN1C2=C(C(=O)O)SC=C2N=C1C(=O)NC(CC1)CCN1C1CC1 JZVCZVTVKDLABR-UHFFFAOYSA-N 0.000 claims description 3
• XPBPVMGKFXTAFJ-UHFFFAOYSA-N 3-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]thieno[3,4-d]imidazole-4-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=CSC(C(O)=O)=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 XPBPVMGKFXTAFJ-UHFFFAOYSA-N 0.000 claims description 3
• BMSWTWHMUPZQBF-UHFFFAOYSA-N 3-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]thieno[3,4-d]imidazole-2,6-dicarboxylic acid Chemical compound OC(=O)C1=NC2=C(C(O)=O)SC=C2N1CC(=NO1)C=C1C1=CC=C(Cl)S1 BMSWTWHMUPZQBF-UHFFFAOYSA-N 0.000 claims description 3
• 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 3
• 125000002947 alkylene group Chemical group 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 3
• 125000005843 halogen group Chemical group 0.000 claims description 3
• RDTIVMPSPJZONT-UHFFFAOYSA-N methyl 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]benzimidazole-5-carboxylate Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=CC(C(=O)OC)=CC=C2N1CC(=NO1)C=C1C1=CC=C(Cl)S1 RDTIVMPSPJZONT-UHFFFAOYSA-N 0.000 claims description 3
• HRUDXLCXQVUPOK-UHFFFAOYSA-N 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-4-(2-hydroxyethoxy)-n-(1-propan-2-ylpiperidin-4-yl)benzimidazole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=C(OCCO)C=CC=C2N1CC(=O)NC1=CC=C(Cl)C=N1 HRUDXLCXQVUPOK-UHFFFAOYSA-N 0.000 claims description 2
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• XQWUKSUHEOQEJF-UHFFFAOYSA-N 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-n-[4-(2-oxo-1,3-oxazolidin-3-yl)phenyl]benzimidazole-2-carboxamide Chemical compound N1=CC(Cl)=CC=C1NC(=O)CN1C2=CC=CC=C2N=C1C(=O)NC1=CC=C(N2C(OCC2)=O)C=C1 XQWUKSUHEOQEJF-UHFFFAOYSA-N 0.000 claims description 2
• OITDJYNYPJJPOP-UHFFFAOYSA-N 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-n-[4-(2-oxopiperazin-1-yl)phenyl]benzimidazole-2-carboxamide Chemical compound N1=CC(Cl)=CC=C1NC(=O)CN1C2=CC=CC=C2N=C1C(=O)NC1=CC=C(N2C(CNCC2)=O)C=C1 OITDJYNYPJJPOP-UHFFFAOYSA-N 0.000 claims description 2
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• PQDRCVHHJPMGKO-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-2-[(1-cyclopropylpiperidin-4-yl)carbamoyl]benzimidazole-5-carboxylic acid Chemical compound C1CN(C2CC2)CCC1NC(=O)C1=NC2=CC(C(=O)O)=CC=C2N1CC(=NO1)C=C1C1=CC=C(Cl)S1 PQDRCVHHJPMGKO-UHFFFAOYSA-N 0.000 claims description 2
• LGGPKSYWUCRBFX-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]-5-(2,2,2-trifluoroethoxy)benzimidazole-4-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=C(C(O)=O)C(OCC(F)(F)F)=CC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 LGGPKSYWUCRBFX-UHFFFAOYSA-N 0.000 claims description 2
• JKSNJQFEXNFFFR-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-4-(3-methoxyazetidine-1-carbonyl)-n-(1-propan-2-ylpiperidin-4-yl)benzimidazole-2-carboxamide Chemical compound C1C(OC)CN1C(=O)C1=CC=CC2=C1N=C(C(=O)NC1CCN(CC1)C(C)C)N2CC1=NOC(C=2SC(Cl)=CC=2)=C1 JKSNJQFEXNFFFR-UHFFFAOYSA-N 0.000 claims description 2
• XBYTVCSWMBIXTL-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-4-(4-hydroxypiperidine-1-carbonyl)-n-(1-propan-2-ylpiperidin-4-yl)benzimidazole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=C(C(=O)N3CCC(O)CC3)C=CC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 XBYTVCSWMBIXTL-UHFFFAOYSA-N 0.000 claims description 2
• WXUDBTONNGBUDV-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-(3-hydroxyazetidine-1-carbonyl)-n-(1-propan-2-ylpiperidin-4-yl)benzimidazole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=CC(C(=O)N3CC(O)C3)=CC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 WXUDBTONNGBUDV-UHFFFAOYSA-N 0.000 claims description 2
• VIHISSHFIYSNCS-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-fluoro-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]benzimidazole-4-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=C(C(O)=O)C(F)=CC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 VIHISSHFIYSNCS-UHFFFAOYSA-N 0.000 claims description 2
• AIJDSNZGBXDOEI-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)benzimidazole-2-carboxamide Chemical compound CN1C(C2)CCC1CC2NC(=O)C1=NC2=CC=CC=C2N1CC(=NO1)C=C1C1=CC=C(Cl)S1 AIJDSNZGBXDOEI-UHFFFAOYSA-N 0.000 claims description 2
• FZRIRJREMKLKLL-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-[4-(2,4-dioxopyrimidin-1-yl)phenyl]benzimidazole-2-carboxamide Chemical compound S1C(Cl)=CC=C1C1=CC(CN2C3=CC=CC=C3N=C2C(=O)NC=2C=CC(=CC=2)N2C(NC(=O)C=C2)=O)=NO1 FZRIRJREMKLKLL-UHFFFAOYSA-N 0.000 claims description 2
• YHWZGFQJFXJTRO-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-[4-(2-oxopiperazin-1-yl)phenyl]benzimidazole-2-carboxamide Chemical compound S1C(Cl)=CC=C1C1=CC(CN2C3=CC=CC=C3N=C2C(=O)NC=2C=CC(=CC=2)N2C(CNCC2)=O)=NO1 YHWZGFQJFXJTRO-UHFFFAOYSA-N 0.000 claims description 2
• SSYDWKAMKBZKQE-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-[4-(4-oxopyridin-1-yl)phenyl]benzimidazole-2-carboxamide Chemical compound S1C(Cl)=CC=C1C1=CC(CN2C3=CC=CC=C3N=C2C(=O)NC=2C=CC(=CC=2)N2C=CC(=O)C=C2)=NO1 SSYDWKAMKBZKQE-UHFFFAOYSA-N 0.000 claims description 2
• NONCMHXGFBXCSL-UHFFFAOYSA-N 2-hydroxyethyl 3-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]benzimidazole-5-carboxylate Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=CC=C(C(=O)OCCO)C=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 NONCMHXGFBXCSL-UHFFFAOYSA-N 0.000 claims description 2
• DDCWSJXZZUOJRT-UHFFFAOYSA-N 3-(4-aminophenyl)-1,3-oxazolidin-2-one Chemical compound C1=CC(N)=CC=C1N1C(=O)OCC1 DDCWSJXZZUOJRT-UHFFFAOYSA-N 0.000 claims description 2
• OWMJNRDDIWQBQB-UHFFFAOYSA-N 3-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-2-[(1-cyclopropylpiperidin-4-yl)carbamoyl]-7-methylbenzimidazole-5-carboxylic acid Chemical compound C1CN(C2CC2)CCC1NC(=O)C1=NC=2C(C)=CC(C(O)=O)=CC=2N1CC(=NO1)C=C1C1=CC=C(Cl)S1 OWMJNRDDIWQBQB-UHFFFAOYSA-N 0.000 claims description 2
• RPCCVIYJCAANPN-UHFFFAOYSA-N 3-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-2-[(1-cyclopropylpiperidin-4-yl)carbamoyl]benzimidazole-4-carboxylic acid Chemical compound C1=C(C=2SC(Cl)=CC=2)ON=C1CN1C=2C(C(=O)O)=CC=CC=2N=C1C(=O)NC(CC1)CCN1C1CC1 RPCCVIYJCAANPN-UHFFFAOYSA-N 0.000 claims description 2
• SNZDWDLKATZKEQ-UHFFFAOYSA-N 3-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]thieno[3,4-d]imidazole-6-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=C(C(O)=O)SC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 SNZDWDLKATZKEQ-UHFFFAOYSA-N 0.000 claims description 2
• GKGOOVHEBPENJV-UHFFFAOYSA-N cyclopropylmethyl 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-2-[(1-cyclopropylpiperidin-4-yl)carbamoyl]benzimidazole-4-carboxylate Chemical compound N1=CC(Cl)=CC=C1NC(=O)CN1C2=CC=CC(C(=O)OCC3CC3)=C2N=C1C(=O)NC1CCN(C2CC2)CC1 GKGOOVHEBPENJV-UHFFFAOYSA-N 0.000 claims description 2
• YRXWWXXMPMFNIQ-UHFFFAOYSA-N cyclopropylmethyl 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]benzimidazole-4-carboxylate Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=C(C(=O)OCC3CC3)C=CC=C2N1CC(=O)NC1=CC=C(Cl)C=N1 YRXWWXXMPMFNIQ-UHFFFAOYSA-N 0.000 claims description 2
• ITMWBKLDVSTUHR-UHFFFAOYSA-N methyl 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-2-[[2-fluoro-4-(pyrrolidine-1-carbonyl)phenyl]carbamoyl]benzimidazole-4-carboxylate Chemical compound C=1C=C(C(=O)N2CCCC2)C=C(F)C=1NC(=O)C1=NC=2C(C(=O)OC)=CC=CC=2N1CC(=O)NC1=CC=C(Cl)C=N1 ITMWBKLDVSTUHR-UHFFFAOYSA-N 0.000 claims description 2
• 239000008194 pharmaceutical composition Substances 0.000 claims description 2
• FUMCMEDOVWJBEI-UHFFFAOYSA-N 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-6-(3-hydroxyazetidine-1-carbonyl)-n-(1-propan-2-ylpiperidin-4-yl)benzimidazole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=CC=C(C(=O)N3CC(O)C3)C=C2N1CC(=O)NC1=CC=C(Cl)C=N1 FUMCMEDOVWJBEI-UHFFFAOYSA-N 0.000 claims 1
• VGDJEZDDAXYCAO-UHFFFAOYSA-N 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-n-[4-(2,4-dioxopyrimidin-1-yl)phenyl]benzimidazole-2-carboxamide Chemical compound N1=CC(Cl)=CC=C1NC(=O)CN1C2=CC=CC=C2N=C1C(=O)NC1=CC=C(N2C(NC(=O)C=C2)=O)C=C1 VGDJEZDDAXYCAO-UHFFFAOYSA-N 0.000 claims 1
• QKCIHUBZWPYBNM-UHFFFAOYSA-N 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-n-[4-(4-oxopyridin-1-yl)phenyl]benzimidazole-2-carboxamide Chemical compound N1=CC(Cl)=CC=C1NC(=O)CN1C2=CC=CC=C2N=C1C(=O)NC1=CC=C(N2C=CC(=O)C=C2)C=C1 QKCIHUBZWPYBNM-UHFFFAOYSA-N 0.000 claims 1
• LXQUJTXPNMSVFX-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-4-(3-hydroxyazetidine-1-carbonyl)-5-(2,2,2-trifluoroethoxy)benzimidazole-2-carboxylic acid Chemical compound C1C(O)CN1C(=O)C1=C(OCC(F)(F)F)C=CC2=C1N=C(C(O)=O)N2CC1=NOC(C=2SC(Cl)=CC=2)=C1 LXQUJTXPNMSVFX-UHFFFAOYSA-N 0.000 claims 1
• UXQXPCCYLZTSKE-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-(2-hydroxyethylsulfonyl)benzimidazole-2-carboxylic acid Chemical compound OC(=O)C1=NC2=CC(S(=O)(=O)CCO)=CC=C2N1CC(=NO1)C=C1C1=CC=C(Cl)S1 UXQXPCCYLZTSKE-UHFFFAOYSA-N 0.000 claims 1
• IOTFMJKDSGFIJG-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-6-(2-hydroxyethylsulfonyl)benzimidazole-2-carboxylic acid Chemical compound C12=CC(S(=O)(=O)CCO)=CC=C2N=C(C(O)=O)N1CC(=NO1)C=C1C1=CC=C(Cl)S1 IOTFMJKDSGFIJG-UHFFFAOYSA-N 0.000 claims 1
• SRSILFCRRJFGDV-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-[4-(2-oxopyrazin-1-yl)phenyl]benzimidazole-2-carboxamide Chemical compound S1C(Cl)=CC=C1C1=CC(CN2C3=CC=CC=C3N=C2C(=O)NC=2C=CC(=CC=2)N2C(C=NC=C2)=O)=NO1 SRSILFCRRJFGDV-UHFFFAOYSA-N 0.000 claims 1
• JZYDTVLYISBCTB-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-[4-(4-oxopiperidin-1-yl)phenyl]benzimidazole-2-carboxamide Chemical compound S1C(Cl)=CC=C1C1=CC(CN2C3=CC=CC=C3N=C2C(=O)NC=2C=CC(=CC=2)N2CCC(=O)CC2)=NO1 JZYDTVLYISBCTB-UHFFFAOYSA-N 0.000 claims 1
• HBCVCIQWVHKFPM-UHFFFAOYSA-N 2-hydroxyethyl 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]benzimidazole-4-carboxylate Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=C(C(=O)OCCO)C=CC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 HBCVCIQWVHKFPM-UHFFFAOYSA-N 0.000 claims 1
• RUOFUBLDYXJNIL-UHFFFAOYSA-N N-(1-propan-2-ylpiperidin-4-yl)-2,3,6,7-tetrahydro-1H-purine-8-carboxamide Chemical compound CC(C)N1CCC(CC1)NC(=O)C1=NC2=C(CNCN2)N1 RUOFUBLDYXJNIL-UHFFFAOYSA-N 0.000 claims 1
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
• 238000000524 positive electrospray ionisation mass spectrometry Methods 0.000 description 170
• 125000001309 chloro group Chemical group Cl* 0.000 description 138
• 238000000034 method Methods 0.000 description 123
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