CA2584979A1 - Indole and benzimidazole derivatives - Google Patents

Info

Publication number

CA2584979A1

CA2584979A1 CA002584979A CA2584979A CA2584979A1 CA 2584979 A1 CA2584979 A1 CA 2584979A1 CA 002584979 A CA002584979 A CA 002584979A CA 2584979 A CA2584979 A CA 2584979A CA 2584979 A1 CA2584979 A1 CA 2584979A1

Authority

CA

Canada

Prior art keywords

substituted

group

benzimidazol

methylpropyl

aminopropyl

Prior art date

2004-10-19

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title abstract description 20
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 title abstract description 10
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 title abstract description 10
• 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title abstract 2
• 229940058303 antinematodal benzimidazole derivative Drugs 0.000 title description 2
• 229940054051 antipsychotic indole derivative Drugs 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 149
• 239000000203 mixture Substances 0.000 claims abstract description 101
• 150000003839 salts Chemical class 0.000 claims abstract description 20
• 229940002612 prodrug Drugs 0.000 claims abstract description 13
• 239000000651 prodrug Substances 0.000 claims abstract description 13
• 150000002148 esters Chemical class 0.000 claims abstract description 12
• 239000003937 drug carrier Substances 0.000 claims abstract description 6
• -1 carboxyl ester Chemical group 0.000 claims description 293
• 125000000623 heterocyclic group Chemical group 0.000 claims description 125
• 125000001072 heteroaryl group Chemical group 0.000 claims description 123
• 125000003118 aryl group Chemical group 0.000 claims description 58
• 125000000217 alkyl group Chemical group 0.000 claims description 57
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 46
• 125000003107 substituted aryl group Chemical group 0.000 claims description 43
• 125000005843 halogen group Chemical group 0.000 claims description 41
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 37
• 238000000034 method Methods 0.000 claims description 37
• 229910052757 nitrogen Inorganic materials 0.000 claims description 37
• 125000001424 substituent group Chemical group 0.000 claims description 37
• 206010028980 Neoplasm Diseases 0.000 claims description 34
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 34
• 229910052799 carbon Inorganic materials 0.000 claims description 32
• 229910052739 hydrogen Inorganic materials 0.000 claims description 32
• 125000003545 alkoxy group Chemical group 0.000 claims description 31
• 239000001257 hydrogen Substances 0.000 claims description 31
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 29
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 28
• 125000003342 alkenyl group Chemical group 0.000 claims description 27
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
• 125000000304 alkynyl group Chemical group 0.000 claims description 26
• 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 24
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
• 125000004442 acylamino group Chemical group 0.000 claims description 23
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 22
• 125000004104 aryloxy group Chemical group 0.000 claims description 20
• 201000011510 cancer Diseases 0.000 claims description 20
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
• 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 20
• 125000002252 acyl group Chemical group 0.000 claims description 18
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 18
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 17
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
• 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims description 16
• 125000000266 alpha-aminoacyl group Chemical group 0.000 claims description 16
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 16
• 125000005415 substituted alkoxy group Chemical group 0.000 claims description 16
• 239000003814 drug Substances 0.000 claims description 14
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
• 125000005017 substituted alkenyl group Chemical group 0.000 claims description 14
• 125000004426 substituted alkynyl group Chemical group 0.000 claims description 14
• 125000002947 alkylene group Chemical group 0.000 claims description 13
• 150000001721 carbon Chemical group 0.000 claims description 13
• 239000003795 chemical substances by application Substances 0.000 claims description 13
• 125000004414 alkyl thio group Chemical group 0.000 claims description 12
• 125000005110 aryl thio group Chemical group 0.000 claims description 12
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 12
• 125000005368 heteroarylthio group Chemical group 0.000 claims description 12
• 238000011282 treatment Methods 0.000 claims description 12
• 239000008194 pharmaceutical composition Substances 0.000 claims description 11
• 208000035475 disorder Diseases 0.000 claims description 9
• 125000001153 fluoro group Chemical group F* 0.000 claims description 9
• 229920002554 vinyl polymer Polymers 0.000 claims description 9
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 8
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 7
• 125000001246 bromo group Chemical group Br* 0.000 claims description 7
• 201000010099 disease Diseases 0.000 claims description 7
• 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 6
• 102000010638 Kinesin Human genes 0.000 claims description 6
• 108010063296 Kinesin Proteins 0.000 claims description 6
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
• 150000003573 thiols Chemical class 0.000 claims description 6
• 125000006334 2,4-difluoro benzoyl group Chemical group [H]C1=C([H])C(C(*)=O)=C(F)C([H])=C1F 0.000 claims description 5
• 125000002672 4-bromobenzoyl group Chemical group BrC1=CC=C(C(=O)*)C=C1 0.000 claims description 5
• 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 claims description 5
• 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 claims description 5
• 230000002062 proliferating effect Effects 0.000 claims description 5
• 125000006288 3,5-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(C([H])=C1F)C([H])([H])* 0.000 claims description 4
• 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims description 4
• 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 4
• 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 claims description 4
• 210000004556 brain Anatomy 0.000 claims description 4
• 230000001413 cellular effect Effects 0.000 claims description 4
• 230000002401 inhibitory effect Effects 0.000 claims description 4
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
• 210000000244 kidney pelvis Anatomy 0.000 claims description 4
• 230000001404 mediated effect Effects 0.000 claims description 4
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
• 125000006291 3-hydroxybenzyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 3
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
• 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims description 3
• 229940122803 Vinca alkaloid Drugs 0.000 claims description 3
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Chemical group C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 3
• 210000001072 colon Anatomy 0.000 claims description 3
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 3
• YJUVPIQHSBRJBU-UHFFFAOYSA-N n-(3-aminopropyl)-n-[1-(1-benzyl-5-chloroindol-2-yl)-2-methylpropyl]benzamide Chemical compound C=1C2=CC(Cl)=CC=C2N(CC=2C=CC=CC=2)C=1C(C(C)C)N(CCCN)C(=O)C1=CC=CC=C1 YJUVPIQHSBRJBU-UHFFFAOYSA-N 0.000 claims description 3
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 3
• 210000002784 stomach Anatomy 0.000 claims description 3
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
• 125000006507 2,4-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(F)C(=C1[H])C([H])([H])* 0.000 claims description 2
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 2
• 125000003541 2-chlorobenzoyl group Chemical group ClC1=C(C(=O)*)C=CC=C1 0.000 claims description 2
• 125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 claims description 2
• QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 2
• 125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 claims description 2
• 125000001999 4-Methoxybenzoyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C(*)=O 0.000 claims description 2
• 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 2
• 206010048832 Colon adenoma Diseases 0.000 claims description 2
• 208000028018 Lymphocytic leukaemia Diseases 0.000 claims description 2
• 208000034578 Multiple myelomas Diseases 0.000 claims description 2
• 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims description 2
• 206010035226 Plasma cell myeloma Diseases 0.000 claims description 2
• 210000000481 breast Anatomy 0.000 claims description 2
• 210000000621 bronchi Anatomy 0.000 claims description 2
• 210000003679 cervix uteri Anatomy 0.000 claims description 2
• 230000001684 chronic effect Effects 0.000 claims description 2
• 125000006639 cyclohexyl carbonyl group Chemical group 0.000 claims description 2
• 210000003238 esophagus Anatomy 0.000 claims description 2
• 125000004245 indazol-3-yl group Chemical group [H]N1N=C(*)C2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 2
• 210000003228 intrahepatic bile duct Anatomy 0.000 claims description 2
• 210000000867 larynx Anatomy 0.000 claims description 2
• 208000032839 leukemia Diseases 0.000 claims description 2
• 210000004185 liver Anatomy 0.000 claims description 2
• 210000004072 lung Anatomy 0.000 claims description 2
• 208000003747 lymphoid leukemia Diseases 0.000 claims description 2
• 201000001441 melanoma Diseases 0.000 claims description 2
• 125000006178 methyl benzyl group Chemical group 0.000 claims description 2
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
• 210000000214 mouth Anatomy 0.000 claims description 2
• 208000025113 myeloid leukemia Diseases 0.000 claims description 2
• UYOVOLBQRKTJIV-UHFFFAOYSA-N n-(3-aminopropyl)-n-[1-(1-benzyl-5-chloroindol-2-yl)-2-methylpropyl]-4-methylbenzamide Chemical compound C=1C2=CC(Cl)=CC=C2N(CC=2C=CC=CC=2)C=1C(C(C)C)N(CCCN)C(=O)C1=CC=C(C)C=C1 UYOVOLBQRKTJIV-UHFFFAOYSA-N 0.000 claims description 2
• CYRIBAMYWWBPOR-UHFFFAOYSA-N n-(3-aminopropyl)-n-[1-[1-(benzenesulfonyl)-5-chloroindol-2-yl]-2-methylpropyl]-4-methylbenzamide Chemical compound C=1C2=CC(Cl)=CC=C2N(S(=O)(=O)C=2C=CC=CC=2)C=1C(C(C)C)N(CCCN)C(=O)C1=CC=C(C)C=C1 CYRIBAMYWWBPOR-UHFFFAOYSA-N 0.000 claims description 2
• 210000001672 ovary Anatomy 0.000 claims description 2
• 210000000496 pancreas Anatomy 0.000 claims description 2
• 210000003800 pharynx Anatomy 0.000 claims description 2
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 2
• WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 2
• 210000002307 prostate Anatomy 0.000 claims description 2
• 210000000664 rectum Anatomy 0.000 claims description 2
• 210000000813 small intestine Anatomy 0.000 claims description 2
• 210000001685 thyroid gland Anatomy 0.000 claims description 2
• 210000003932 urinary bladder Anatomy 0.000 claims description 2
• 229960000575 trastuzumab Drugs 0.000 claims 4
• VVIAGPKUTFNRDU-UHFFFAOYSA-N 6S-folinic acid Natural products C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 VVIAGPKUTFNRDU-UHFFFAOYSA-N 0.000 claims 2
• CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims 2
• GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims 2
• 239000005517 L01XE01 - Imatinib Substances 0.000 claims 2
• ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 claims 2
• 229930012538 Paclitaxel Natural products 0.000 claims 2
• 229940045799 anthracyclines and related substance Drugs 0.000 claims 2
• VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 claims 2
• 229960004562 carboplatin Drugs 0.000 claims 2
• DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims 2
• 229960004316 cisplatin Drugs 0.000 claims 2
• 229960004397 cyclophosphamide Drugs 0.000 claims 2
• 229960003668 docetaxel Drugs 0.000 claims 2
• 229960002949 fluorouracil Drugs 0.000 claims 2
• VVIAGPKUTFNRDU-ABLWVSNPSA-N folinic acid Chemical compound C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 VVIAGPKUTFNRDU-ABLWVSNPSA-N 0.000 claims 2
• 235000008191 folinic acid Nutrition 0.000 claims 2
• 239000011672 folinic acid Substances 0.000 claims 2
• 229960005277 gemcitabine Drugs 0.000 claims 2
• SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 claims 2
• 229960002411 imatinib Drugs 0.000 claims 2
• KTUFNOKKBVMGRW-UHFFFAOYSA-N imatinib Chemical compound C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 KTUFNOKKBVMGRW-UHFFFAOYSA-N 0.000 claims 2
• 229960004768 irinotecan Drugs 0.000 claims 2
• UWKQSNNFCGGAFS-XIFFEERXSA-N irinotecan Chemical compound C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 UWKQSNNFCGGAFS-XIFFEERXSA-N 0.000 claims 2
• 229960001691 leucovorin Drugs 0.000 claims 2
• 229960001592 paclitaxel Drugs 0.000 claims 2
• 229960004641 rituximab Drugs 0.000 claims 2
• RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims 2
• 229950006410 tezacitabine Drugs 0.000 claims 2
• GFFXZLZWLOBBLO-ASKVSEFXSA-N tezacitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(=C/F)/[C@H](O)[C@@H](CO)O1 GFFXZLZWLOBBLO-ASKVSEFXSA-N 0.000 claims 2
• 229960000303 topotecan Drugs 0.000 claims 2
• UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 claims 2
• GPLAIVVSVBXALK-HHHXNRCGSA-N 2-(2-aminoethyl)-3-[(1r)-1-(1-benzyl-5-bromobenzimidazol-2-yl)-2-methylpropyl]-7-methylquinazolin-4-one Chemical compound C1([C@@H](C(C)C)N2C(C3=CC=C(C)C=C3N=C2CCN)=O)=NC2=CC(Br)=CC=C2N1CC1=CC=CC=C1 GPLAIVVSVBXALK-HHHXNRCGSA-N 0.000 claims 1
• KREYLRNYOGSXLM-HHHXNRCGSA-N 2-(3-aminopropanoylamino)-n-[(1r)-1-(1-benzyl-5-bromobenzimidazol-2-yl)-2-methylpropyl]-4-methylbenzamide Chemical compound N([C@H](C(C)C)C=1N(C2=CC=C(Br)C=C2N=1)CC=1C=CC=CC=1)C(=O)C1=CC=C(C)C=C1NC(=O)CCN KREYLRNYOGSXLM-HHHXNRCGSA-N 0.000 claims 1
• KWJDWYSFWOBHHV-RCZVLFRGSA-N [(2r,4r)-4-hydroxy-2-[1-[(3-hydroxyphenyl)methyl]-5-methylbenzimidazol-2-yl]pyrrolidin-1-yl]-(4-methylphenyl)methanone Chemical compound C1=CC(C)=CC=C1C(=O)N1[C@@H](C=2N(C3=CC=C(C)C=C3N=2)CC=2C=C(O)C=CC=2)C[C@@H](O)C1 KWJDWYSFWOBHHV-RCZVLFRGSA-N 0.000 claims 1
• 125000006289 hydroxybenzyl group Chemical group 0.000 claims 1
• 238000004519 manufacturing process Methods 0.000 claims 1
• PQACBBDWELWUSL-HHHXNRCGSA-N n-(3-aminopropyl)-2,4-difluoro-n-[(1r)-1-[1-[(3-fluorophenyl)methyl]-5-methylbenzimidazol-2-yl]-2-methylpropyl]benzamide Chemical compound NCCCN([C@H](C(C)C)C=1N(C2=CC=C(C)C=C2N=1)CC=1C=C(F)C=CC=1)C(=O)C1=CC=C(F)C=C1F PQACBBDWELWUSL-HHHXNRCGSA-N 0.000 claims 1
• PVPWWDHDFSICHB-HHHXNRCGSA-N n-(3-aminopropyl)-2,6-difluoro-n-[(1r)-1-[1-[(3-fluorophenyl)methyl]-5-methylbenzimidazol-2-yl]-2-methylpropyl]benzamide Chemical compound NCCCN([C@H](C(C)C)C=1N(C2=CC=C(C)C=C2N=1)CC=1C=C(F)C=CC=1)C(=O)C1=C(F)C=CC=C1F PVPWWDHDFSICHB-HHHXNRCGSA-N 0.000 claims 1
• XZSZEPDNLSGHNY-HHHXNRCGSA-N n-(3-aminopropyl)-2-fluoro-n-[(1r)-1-[1-[(3-fluorophenyl)methyl]-5-methylbenzimidazol-2-yl]-2-methylpropyl]benzamide Chemical compound NCCCN([C@H](C(C)C)C=1N(C2=CC=C(C)C=C2N=1)CC=1C=C(F)C=CC=1)C(=O)C1=CC=CC=C1F XZSZEPDNLSGHNY-HHHXNRCGSA-N 0.000 claims 1
• SGLDLCIHCIKKAQ-MUUNZHRXSA-N n-(3-aminopropyl)-3-fluoro-n-[(1r)-1-[1-[(3-fluorophenyl)methyl]-5-methylbenzimidazol-2-yl]-2-methylpropyl]-4-methylbenzamide Chemical compound NCCCN([C@H](C(C)C)C=1N(C2=CC=C(C)C=C2N=1)CC=1C=C(F)C=CC=1)C(=O)C1=CC=C(C)C(F)=C1 SGLDLCIHCIKKAQ-MUUNZHRXSA-N 0.000 claims 1
• KHRGMOLQJLZXFO-HHHXNRCGSA-N n-(3-aminopropyl)-n-[(1r)-1-(1-benzyl-5-bromobenzimidazol-2-yl)-2-methylpropyl]-4-methylbenzamide Chemical compound NCCCN([C@H](C(C)C)C=1N(C2=CC=C(Br)C=C2N=1)CC=1C=CC=CC=1)C(=O)C1=CC=C(C)C=C1 KHRGMOLQJLZXFO-HHHXNRCGSA-N 0.000 claims 1
• NKIFOGKGKVRTPL-RUZDIDTESA-N n-(3-aminopropyl)-n-[(1r)-1-(1-benzyl-5-bromobenzimidazol-2-yl)propyl]-4-methylbenzamide Chemical compound NCCCN([C@H](CC)C=1N(C2=CC=C(Br)C=C2N=1)CC=1C=CC=CC=1)C(=O)C1=CC=C(C)C=C1 NKIFOGKGKVRTPL-RUZDIDTESA-N 0.000 claims 1
• NJQJRKYUEHNZDZ-XMMPIXPASA-N n-(3-aminopropyl)-n-[(1r)-1-(1-benzyl-5-bromobenzimidazol-2-yl)propyl]benzamide Chemical compound NCCCN([C@H](CC)C=1N(C2=CC=C(Br)C=C2N=1)CC=1C=CC=CC=1)C(=O)C1=CC=CC=C1 NJQJRKYUEHNZDZ-XMMPIXPASA-N 0.000 claims 1
• JCYQCPAMASEMPJ-HHHXNRCGSA-N n-(3-aminopropyl)-n-[(1r)-1-(1-benzyl-5-chlorobenzimidazol-2-yl)-2-methylpropyl]-4-methylbenzamide Chemical compound NCCCN([C@H](C(C)C)C=1N(C2=CC=C(Cl)C=C2N=1)CC=1C=CC=CC=1)C(=O)C1=CC=C(C)C=C1 JCYQCPAMASEMPJ-HHHXNRCGSA-N 0.000 claims 1
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• NXGRWVXRDOEIKS-AREMUKBSSA-N n-(3-aminopropyl)-n-[(1r)-1-[1-[(3-fluorophenyl)methyl]-5-methylbenzimidazol-2-yl]-2-methylpropyl]pyridine-4-carboxamide Chemical compound NCCCN([C@H](C(C)C)C=1N(C2=CC=C(C)C=C2N=1)CC=1C=C(F)C=CC=1)C(=O)C1=CC=NC=C1 NXGRWVXRDOEIKS-AREMUKBSSA-N 0.000 claims 1
• SDZFSYKJPOMMBP-MUUNZHRXSA-N n-(3-aminopropyl)-n-[(1r)-1-[1-[(3-hydroxyphenyl)methyl]-5-methylbenzimidazol-2-yl]-2-methylpropyl]-4-methylbenzamide Chemical compound NCCCN([C@H](C(C)C)C=1N(C2=CC=C(C)C=C2N=1)CC=1C=C(O)C=CC=1)C(=O)C1=CC=C(C)C=C1 SDZFSYKJPOMMBP-MUUNZHRXSA-N 0.000 claims 1
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• LYYWDTJPPMTSCQ-AREMUKBSSA-N n-(3-aminopropyl)-n-[(1r)-1-[5-bromo-1-[(3-chlorophenyl)methyl]benzimidazol-2-yl]-2-methylpropyl]benzamide Chemical compound NCCCN([C@H](C(C)C)C=1N(C2=CC=C(Br)C=C2N=1)CC=1C=C(Cl)C=CC=1)C(=O)C1=CC=CC=C1 LYYWDTJPPMTSCQ-AREMUKBSSA-N 0.000 claims 1
• UDZYZKIPXHFRHE-GDLZYMKVSA-N n-(3-aminopropyl)-n-[(1r)-1-[5-ethyl-1-[(3-fluorophenyl)methyl]benzimidazol-2-yl]-2-methylpropyl]-4-methylbenzamide Chemical compound C1([C@@H](C(C)C)N(CCCN)C(=O)C=2C=CC(C)=CC=2)=NC2=CC(CC)=CC=C2N1CC1=CC=CC(F)=C1 UDZYZKIPXHFRHE-GDLZYMKVSA-N 0.000 claims 1
• CIGXKHLIJGDCKK-GDLZYMKVSA-N n-(3-aminopropyl)-n-[(1r)-1-[5-ethyl-1-[(3-hydroxyphenyl)methyl]benzimidazol-2-yl]-2-methylpropyl]-4-methylbenzamide Chemical compound C1([C@@H](C(C)C)N(CCCN)C(=O)C=2C=CC(C)=CC=2)=NC2=CC(CC)=CC=C2N1CC1=CC=CC(O)=C1 CIGXKHLIJGDCKK-GDLZYMKVSA-N 0.000 claims 1
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