JP2008517057A5 - - Google Patents
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- Publication number
- JP2008517057A5 JP2008517057A5 JP2007537929A JP2007537929A JP2008517057A5 JP 2008517057 A5 JP2008517057 A5 JP 2008517057A5 JP 2007537929 A JP2007537929 A JP 2007537929A JP 2007537929 A JP2007537929 A JP 2007537929A JP 2008517057 A5 JP2008517057 A5 JP 2008517057A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- benzimidazol
- methylpropyl
- group
- aminopropyl
- Prior art date
- 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.)
- Pending
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- -1 carboxyl ester Chemical class 0.000 claims 93
- 150000001875 compounds Chemical class 0.000 claims 31
- 125000000623 heterocyclic group Chemical group 0.000 claims 26
- 125000001072 heteroaryl group Chemical group 0.000 claims 24
- 125000000217 alkyl group Chemical group 0.000 claims 17
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims 13
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 12
- 125000005843 halogen group Chemical group 0.000 claims 12
- 239000000203 mixture Substances 0.000 claims 12
- 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims 10
- 125000003118 aryl group Chemical group 0.000 claims 10
- 229910052757 nitrogen Inorganic materials 0.000 claims 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- 206010028980 Neoplasm Diseases 0.000 claims 7
- 201000011510 cancer Diseases 0.000 claims 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 7
- 125000000547 substituted alkyl group Chemical group 0.000 claims 7
- 125000003107 substituted aryl group Chemical group 0.000 claims 7
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000004442 acylamino group Chemical group 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 5
- 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 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 229960004562 carboplatin Drugs 0.000 claims 4
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims 4
- 229960004316 cisplatin Drugs 0.000 claims 4
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 229960000575 trastuzumab Drugs 0.000 claims 4
- 125000006288 3,5-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(C([H])=C1F)C([H])([H])* 0.000 claims 3
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims 3
- 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 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000002252 acyl group Chemical group 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 150000002148 esters Chemical class 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 229940002612 prodrug Drugs 0.000 claims 3
- 239000000651 prodrug Substances 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 3
- 125000006334 2,4-difluoro benzoyl group Chemical group [H]C1=C([H])C(C(*)=O)=C(F)C([H])=C1F 0.000 claims 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims 2
- 125000006291 3-hydroxybenzyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(=C1[H])C([H])([H])* 0.000 claims 2
- 125000002672 4-bromobenzoyl group Chemical group BrC1=CC=C(C(=O)*)C=C1 0.000 claims 2
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 claims 2
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 2
- 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
- 229940122803 Vinca alkaloid Drugs 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 125000000266 alpha-aminoacyl group Chemical group 0.000 claims 2
- 229940045799 anthracyclines and related substance Drugs 0.000 claims 2
- 125000005110 aryl thio group Chemical group 0.000 claims 2
- 125000004104 aryloxy group Chemical group 0.000 claims 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 229960004397 cyclophosphamide Drugs 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 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
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 2
- 125000005368 heteroarylthio group Chemical group 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
- 125000004245 indazol-3-yl group Chemical group [H]N1N=C(*)C2=C([H])C([H])=C([H])C([H])=C12 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
- 210000003734 kidney Anatomy 0.000 claims 2
- 229960001691 leucovorin Drugs 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 2
- 208000025113 myeloid leukemia Diseases 0.000 claims 2
- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 claims 2
- 230000002062 proliferating effect Effects 0.000 claims 2
- 229960004641 rituximab Drugs 0.000 claims 2
- 125000005415 substituted alkoxy group Chemical group 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
- 229950006410 tezacitabine Drugs 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
- 229920002554 vinyl polymer Polymers 0.000 claims 2
- 125000006507 2,4-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(F)C(=C1[H])C([H])([H])* 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
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 1
- 125000003541 2-chlorobenzoyl group Chemical group ClC1=C(C(=O)*)C=CC=C1 0.000 claims 1
- 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 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims 1
- 125000001999 4-Methoxybenzoyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C(*)=O 0.000 claims 1
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims 1
- 102000010638 Kinesin Human genes 0.000 claims 1
- 108010063296 Kinesin Proteins 0.000 claims 1
- 208000028018 Lymphocytic leukaemia Diseases 0.000 claims 1
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims 1
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims 1
- 229930012538 Paclitaxel Natural products 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
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 210000004556 brain Anatomy 0.000 claims 1
- 210000000481 breast Anatomy 0.000 claims 1
- 210000000621 bronchi Anatomy 0.000 claims 1
- 125000006309 butyl amino group Chemical group 0.000 claims 1
- 230000001413 cellular effect Effects 0.000 claims 1
- 210000003679 cervix uteri Anatomy 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 210000001072 colon Anatomy 0.000 claims 1
- GIVGDJZVMHYWDM-UHFFFAOYSA-N cyanourea Chemical compound NC(=O)NC#N GIVGDJZVMHYWDM-UHFFFAOYSA-N 0.000 claims 1
- 125000006311 cyclobutyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000006639 cyclohexyl carbonyl group Chemical group 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 210000003228 intrahepatic bile duct Anatomy 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 210000000867 larynx Anatomy 0.000 claims 1
- 210000004185 liver Anatomy 0.000 claims 1
- 210000004072 lung Anatomy 0.000 claims 1
- 208000003747 lymphoid leukemia Diseases 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- 210000000214 mouth Anatomy 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
- 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
- PARNBIFQUXKPDM-RUZDIDTESA-N n-(3-aminopropyl)-n-[(1r)-1-(1-benzyl-5-chlorobenzimidazol-2-yl)propyl]-4-methylbenzamide Chemical compound NCCCN([C@H](CC)C=1N(C2=CC=C(Cl)C=C2N=1)CC=1C=CC=CC=1)C(=O)C1=CC=C(C)C=C1 PARNBIFQUXKPDM-RUZDIDTESA-N 0.000 claims 1
- HWKPUALZJIRGJD-GDLZYMKVSA-N n-(3-aminopropyl)-n-[(1r)-1-(1-benzyl-5-ethenylbenzimidazol-2-yl)-2-methylpropyl]-4-methylbenzamide Chemical compound NCCCN([C@H](C(C)C)C=1N(C2=CC=C(C=C)C=C2N=1)CC=1C=CC=CC=1)C(=O)C1=CC=C(C)C=C1 HWKPUALZJIRGJD-GDLZYMKVSA-N 0.000 claims 1
- VTUUGMIRDAVSSW-GDLZYMKVSA-N n-(3-aminopropyl)-n-[(1r)-1-(1-benzyl-5-ethylbenzimidazol-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=C1 VTUUGMIRDAVSSW-GDLZYMKVSA-N 0.000 claims 1
- DCFCJPNUTQSCBS-GDLZYMKVSA-N n-(3-aminopropyl)-n-[(1r)-1-(1-benzyl-5-ethynylbenzimidazol-2-yl)-2-methylpropyl]-4-methylbenzamide Chemical compound NCCCN([C@H](C(C)C)C=1N(C2=CC=C(C=C2N=1)C#C)CC=1C=CC=CC=1)C(=O)C1=CC=C(C)C=C1 DCFCJPNUTQSCBS-GDLZYMKVSA-N 0.000 claims 1
- FRQFFVCVXPLHJC-MUUNZHRXSA-N n-(3-aminopropyl)-n-[(1r)-1-(1-benzyl-5-methoxybenzimidazol-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(OC)=CC=C2N1CC1=CC=CC=C1 FRQFFVCVXPLHJC-MUUNZHRXSA-N 0.000 claims 1
- OHDCXPKNIOMNFO-MUUNZHRXSA-N n-(3-aminopropyl)-n-[(1r)-1-(1-benzyl-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=CC=CC=1)C(=O)C1=CC=C(C)C=C1 OHDCXPKNIOMNFO-MUUNZHRXSA-N 0.000 claims 1
- QKIRQPVEBFNRJQ-MGBGTMOVSA-N n-(3-aminopropyl)-n-[(1r)-1-(1-benzyl-5-phenylbenzimidazol-2-yl)-2-methylpropyl]-4-methylbenzamide Chemical compound NCCCN([C@H](C(C)C)C=1N(C2=CC=C(C=C2N=1)C=1C=CC=CC=1)CC=1C=CC=CC=1)C(=O)C1=CC=C(C)C=C1 QKIRQPVEBFNRJQ-MGBGTMOVSA-N 0.000 claims 1
- GJFNLSZGZLUVPY-AREMUKBSSA-N n-(3-aminopropyl)-n-[(1r)-1-(1-benzylbenzimidazol-2-yl)-2-methylpropyl]-4-bromobenzamide Chemical compound NCCCN([C@H](C(C)C)C=1N(C2=CC=CC=C2N=1)CC=1C=CC=CC=1)C(=O)C1=CC=C(Br)C=C1 GJFNLSZGZLUVPY-AREMUKBSSA-N 0.000 claims 1
- NNJKNBQOQVYXFJ-AREMUKBSSA-N n-(3-aminopropyl)-n-[(1r)-1-(1-benzylbenzimidazol-2-yl)-2-methylpropyl]-4-chlorobenzamide Chemical compound NCCCN([C@H](C(C)C)C=1N(C2=CC=CC=C2N=1)CC=1C=CC=CC=1)C(=O)C1=CC=C(Cl)C=C1 NNJKNBQOQVYXFJ-AREMUKBSSA-N 0.000 claims 1
- GUCJEOOLEAZTSH-HHHXNRCGSA-N n-(3-aminopropyl)-n-[(1r)-1-(1-benzylbenzimidazol-2-yl)-2-methylpropyl]-4-methylbenzamide Chemical compound NCCCN([C@H](C(C)C)C=1N(C2=CC=CC=C2N=1)CC=1C=CC=CC=1)C(=O)C1=CC=C(C)C=C1 GUCJEOOLEAZTSH-HHHXNRCGSA-N 0.000 claims 1
- IIASYHHOPFYGJR-GDLZYMKVSA-N n-(3-aminopropyl)-n-[(1r)-1-[1-[(3-fluorophenyl)methyl]-5-methylbenzimidazol-2-yl]-2-methylpropyl]-3,4-dimethylbenzamide 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(C)=C1 IIASYHHOPFYGJR-GDLZYMKVSA-N 0.000 claims 1
- LCBUWIFSZMWXEP-HHHXNRCGSA-N n-(3-aminopropyl)-n-[(1r)-1-[1-[(3-fluorophenyl)methyl]-5-methylbenzimidazol-2-yl]-2-methylpropyl]-4-hydroxybenzamide 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(O)C=C1 LCBUWIFSZMWXEP-HHHXNRCGSA-N 0.000 claims 1
- PNRWQDFIKYNZEK-MUUNZHRXSA-N n-(3-aminopropyl)-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=C1 PNRWQDFIKYNZEK-MUUNZHRXSA-N 0.000 claims 1
- LDXNMBUHPLGQDG-HHHXNRCGSA-N n-(3-aminopropyl)-n-[(1r)-1-[1-[(3-fluorophenyl)methyl]-5-methylbenzimidazol-2-yl]-2-methylpropyl]-4-nitrobenzamide 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([N+]([O-])=O)C=C1 LDXNMBUHPLGQDG-HHHXNRCGSA-N 0.000 claims 1
- HFWRNHUYZJXUSJ-WJOKGBTCSA-N n-(3-aminopropyl)-n-[(1r)-1-[1-[(3-fluorophenyl)methyl]-5-methylbenzimidazol-2-yl]-2-methylpropyl]naphthalene-2-carboxamide Chemical compound C1([C@H](N(CCCN)C(=O)C=2C=C3C=CC=CC3=CC=2)C(C)C)=NC2=CC(C)=CC=C2N1CC1=CC=CC(F)=C1 HFWRNHUYZJXUSJ-WJOKGBTCSA-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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- 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 1
- ZPABUCVNBQTPGT-SSEXGKCCSA-N n-[(1r)-1-(1-benzyl-5-chlorobenzimidazol-2-yl)-2-methylpropyl]-4-methyl-n-[3-(propan-2-ylamino)propyl]benzamide Chemical compound C1([C@@H](C(C)C)N(CCCNC(C)C)C(=O)C=2C=CC(C)=CC=2)=NC2=CC(Cl)=CC=C2N1CC1=CC=CC=C1 ZPABUCVNBQTPGT-SSEXGKCCSA-N 0.000 claims 1
- ODGPLSMRWBKAED-HHHXNRCGSA-N n-[(1r)-1-(1-benzyl-5-chlorobenzimidazol-2-yl)-2-methylpropyl]-n-[3-(carbamoylamino)propyl]-4-methylbenzamide Chemical compound NC(=O)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 ODGPLSMRWBKAED-HHHXNRCGSA-N 0.000 claims 1
- NGINMYQDMOKDDG-UUWRZZSWSA-N n-[(1r)-1-(1-benzyl-5-chlorobenzimidazol-2-yl)-2-methylpropyl]-n-[3-(cyclohexylmethylamino)propyl]-4-methylbenzamide Chemical compound C=1C=C(C)C=CC=1C(=O)N([C@H](C(C)C)C=1N(C2=CC=C(Cl)C=C2N=1)CC=1C=CC=CC=1)CCCNCC1CCCCC1 NGINMYQDMOKDDG-UUWRZZSWSA-N 0.000 claims 1
- MGYBJCLYQKOJJM-WJOKGBTCSA-N n-[(1r)-1-(1-benzyl-5-chlorobenzimidazol-2-yl)-2-methylpropyl]-n-[3-(diethylamino)propyl]-4-methylbenzamide Chemical compound C1([C@@H](C(C)C)N(CCCN(CC)CC)C(=O)C=2C=CC(C)=CC=2)=NC2=CC(Cl)=CC=C2N1CC1=CC=CC=C1 MGYBJCLYQKOJJM-WJOKGBTCSA-N 0.000 claims 1
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- XDFMABGPLDTWEB-GDLZYMKVSA-N n-[(1r)-1-[1-[(3-acetamidophenyl)methyl]-5-bromobenzimidazol-2-yl]-2-methylpropyl]-n-(3-aminopropyl)-4-methylbenzamide Chemical compound NCCCN([C@H](C(C)C)C=1N(C2=CC=C(Br)C=C2N=1)CC=1C=C(NC(C)=O)C=CC=1)C(=O)C1=CC=C(C)C=C1 XDFMABGPLDTWEB-GDLZYMKVSA-N 0.000 claims 1
- RFDRCQVBVSXKGB-UUWRZZSWSA-N n-[3-(benzylamino)propyl]-n-[(1r)-1-(1-benzyl-5-chlorobenzimidazol-2-yl)-2-methylpropyl]-4-methylbenzamide Chemical compound C=1C=C(C)C=CC=1C(=O)N([C@H](C(C)C)C=1N(C2=CC=C(Cl)C=C2N=1)CC=1C=CC=CC=1)CCCNCC1=CC=CC=C1 RFDRCQVBVSXKGB-UUWRZZSWSA-N 0.000 claims 1
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- DFPAKSUCGFBDDF-UHFFFAOYSA-N nicotinic acid amide Natural products NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 1
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| CN101027309B (zh) * | 2004-08-18 | 2010-10-27 | 阿斯利康(瑞典)有限公司 | 所选择的稠合嘧啶酮的对映体和在治疗和预防癌症中的用途 |
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2005
- 2005-10-14 JP JP2007537929A patent/JP2008517057A/ja active Pending
- 2005-10-14 CA CA002584979A patent/CA2584979A1/en not_active Abandoned
- 2005-10-14 EP EP05851219A patent/EP1807399A2/en not_active Withdrawn
- 2005-10-14 WO PCT/US2005/036803 patent/WO2006049835A2/en not_active Ceased
- 2005-10-14 US US11/251,440 patent/US7608723B2/en not_active Expired - Fee Related
- 2005-10-14 KR KR1020077011415A patent/KR20070072598A/ko not_active Withdrawn
- 2005-10-14 AU AU2005301133A patent/AU2005301133A1/en not_active Abandoned
- 2005-10-14 US US11/665,956 patent/US8008335B2/en not_active Expired - Fee Related
- 2005-10-14 BR BRPI0517314-0A patent/BRPI0517314A/pt not_active IP Right Cessation
- 2005-10-14 EP EP10181182A patent/EP2275412A1/en not_active Withdrawn
- 2005-10-14 MX MX2007004699A patent/MX2007004699A/es not_active Application Discontinuation
- 2005-10-14 RU RU2007118523/04A patent/RU2007118523A/ru not_active Application Discontinuation
- 2005-10-14 CN CNA2005800402742A patent/CN101233115A/zh active Pending