JP2008517057A5 - - Google Patents
Download PDFInfo
- 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
Links
- -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
- VXNNIYSLNBGDRE-HHHXNRCGSA-N n-(3-aminopropyl)-n-[(1r)-1-[1-[(4-chlorophenyl)methyl]-6-fluorobenzimidazol-2-yl]-2-methylpropyl]-4-methylbenzamide Chemical compound NCCCN([C@H](C(C)C)C=1N(C2=CC(F)=CC=C2N=1)CC=1C=CC(Cl)=CC=1)C(=O)C1=CC=C(C)C=C1 VXNNIYSLNBGDRE-HHHXNRCGSA-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
- 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 1
- 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 1
- 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
- ZNMLHGYEYVXRMS-MUUNZHRXSA-N n-[(1r)-1-(1-benzyl-5-chlorobenzimidazol-2-yl)-2-methylpropyl]-n-[3-[carbamoyl(cyano)amino]propyl]-4-methylbenzamide Chemical compound N#CN(C(N)=O)CCCN([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 ZNMLHGYEYVXRMS-MUUNZHRXSA-N 0.000 claims 1
- 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
- 229960003966 nicotinamide Drugs 0.000 claims 1
- 235000005152 nicotinamide Nutrition 0.000 claims 1
- 239000011570 nicotinamide Substances 0.000 claims 1
- DFPAKSUCGFBDDF-UHFFFAOYSA-N nicotinic acid amide Natural products NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 1
- 210000001672 ovary Anatomy 0.000 claims 1
- 229960001592 paclitaxel Drugs 0.000 claims 1
- 210000000496 pancreas Anatomy 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 210000003800 pharynx Anatomy 0.000 claims 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 1
- 210000002307 prostate Anatomy 0.000 claims 1
- 210000000664 rectum Anatomy 0.000 claims 1
- 210000000813 small intestine Anatomy 0.000 claims 1
- 210000002784 stomach Anatomy 0.000 claims 1
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 1
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 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 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 150000003573 thiols Chemical class 0.000 claims 1
- 210000001685 thyroid gland Anatomy 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 0 CC1(*)C=C2N=C(C(*)(N(*)*)[Re])N(*)C2=CC=C1 Chemical compound CC1(*)C=C2N=C(C(*)(N(*)*)[Re])N(*)C2=CC=C1 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US62038504P | 2004-10-19 | 2004-10-19 | |
| PCT/US2005/036803 WO2006049835A2 (en) | 2004-10-19 | 2005-10-14 | Indole and benzimidazole derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008517057A JP2008517057A (ja) | 2008-05-22 |
| JP2008517057A5 true JP2008517057A5 (enExample) | 2008-09-11 |
Family
ID=36123937
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007537929A Pending JP2008517057A (ja) | 2004-10-19 | 2005-10-14 | インドールおよびベンゾイミダゾール誘導体 |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US7608723B2 (enExample) |
| EP (2) | EP1807399A2 (enExample) |
| JP (1) | JP2008517057A (enExample) |
| KR (1) | KR20070072598A (enExample) |
| CN (1) | CN101233115A (enExample) |
| AU (1) | AU2005301133A1 (enExample) |
| BR (1) | BRPI0517314A (enExample) |
| CA (1) | CA2584979A1 (enExample) |
| MX (1) | MX2007004699A (enExample) |
| RU (1) | RU2007118523A (enExample) |
| WO (1) | WO2006049835A2 (enExample) |
Families Citing this family (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3947758B2 (ja) * | 2003-03-07 | 2007-07-25 | アストラゼネカ アクチボラグ | 新規縮合ヘテロサイクル及びその使用 |
| UA84954C2 (ru) * | 2004-07-22 | 2008-12-10 | Astrazeneca Ab | Конденсированные пиримидоны, пригодные для лечения и профилактики злокачественного новообразования |
| AU2005273705B8 (en) * | 2004-08-18 | 2010-01-28 | Astrazeneca Ab | Enantiomers of selected fused pyrimidones and uses in the treatment and prevention of cancer |
| EP1807399A2 (en) * | 2004-10-19 | 2007-07-18 | Novartis Vaccines and Diagnostics, Inc. | Indole and benzimidazole derivatives |
| US20100093767A1 (en) * | 2004-12-03 | 2010-04-15 | Takeda San Diego, Inc. | Mitotic Kinase Inhibitors |
| CA2668661A1 (en) * | 2006-11-13 | 2008-05-29 | Novartis Ag | Substituted pyrazole and triazole compounds as ksp inhibitors |
| MX2009007260A (es) * | 2007-01-05 | 2009-07-10 | Novartis Ag | Derivados de imidazol como inhibidores de proteina de huso de cinesina (eg-5). |
| DE102007037579B4 (de) | 2007-08-09 | 2012-05-16 | Emc Microcollections Gmbh | Neue Benzimidazol-2-yl-alkylamine und ihre Anwendung als mikrobizide Wirkstoffe |
| US9643922B2 (en) * | 2008-08-18 | 2017-05-09 | Yale University | MIF modulators |
| EA201170349A1 (ru) * | 2008-08-18 | 2011-08-30 | Йейл Юниверсити | Модуляторы mif |
| US9540322B2 (en) | 2008-08-18 | 2017-01-10 | Yale University | MIF modulators |
| PE20120493A1 (es) | 2009-06-29 | 2012-05-20 | Incyte Corp | Pirimidinonas como inhibidores de pi3k |
| US8759359B2 (en) | 2009-12-18 | 2014-06-24 | Incyte Corporation | Substituted heteroaryl fused derivatives as PI3K inhibitors |
| TW201130842A (en) * | 2009-12-18 | 2011-09-16 | Incyte Corp | Substituted fused aryl and heteroaryl derivatives as PI3K inhibitors |
| AR081823A1 (es) | 2010-04-14 | 2012-10-24 | Incyte Corp | DERIVADOS FUSIONADOS COMO INHIBIDORES DE PI3Kd |
| US8748626B2 (en) * | 2010-04-15 | 2014-06-10 | Novartis Ag | Oxazole and thiazole compounds as KSP inhibitors |
| AU2011239977B2 (en) | 2010-04-15 | 2014-11-27 | Novartis Ag | Triazole compounds as KSP inhibitors |
| WO2011163195A1 (en) | 2010-06-21 | 2011-12-29 | Incyte Corporation | Fused pyrrole derivatives as pi3k inhibitors |
| ES2764848T3 (es) | 2010-12-20 | 2020-06-04 | Incyte Holdings Corp | N-(1-(fenilo sustituido)etilo)-9H-purina-6-aminas como inhibidores de PI3K |
| WO2012125629A1 (en) | 2011-03-14 | 2012-09-20 | Incyte Corporation | Substituted diamino-pyrimidine and diamino-pyridine derivatives as pi3k inhibitors |
| WO2012135009A1 (en) | 2011-03-25 | 2012-10-04 | Incyte Corporation | Pyrimidine-4,6-diamine derivatives as pi3k inhibitors |
| KR20230038593A (ko) | 2011-09-02 | 2023-03-20 | 인사이트 홀딩스 코포레이션 | Ｐｉ３ｋ 억제제로서 헤테로시클릴아민 |
| CN102627578B (zh) * | 2011-10-20 | 2014-06-11 | 南京大学 | 苯基苄胺类化合物及其应用 |
| JP5977837B2 (ja) | 2011-12-21 | 2016-08-24 | ノヴィラ・セラピューティクス・インコーポレイテッド | Ｂ型肝炎抗ウイルス剤 |
| AR090548A1 (es) | 2012-04-02 | 2014-11-19 | Incyte Corp | Azaheterociclobencilaminas biciclicas como inhibidores de pi3k |
| CN102603544A (zh) * | 2012-04-06 | 2012-07-25 | 南京大学 | 一种抗炎化合物、其制备及其用途 |
| MX373711B (es) | 2012-08-28 | 2020-05-08 | Janssen Sciences Ireland Uc | Sulfamoilarilamidas y su uso como medicamentos para el tratamiento de la hepatitis b. |
| DK2961732T3 (en) | 2013-02-28 | 2017-07-10 | Janssen Sciences Ireland Uc | SULFAMOYLARYLAMIDS AND USE THEREOF AS MEDICINES TO TREAT HEPATITIS B |
| CN105102451B (zh) | 2013-04-03 | 2018-09-18 | 爱尔兰詹森科学公司 | N-苯基-氨甲酰衍生物及其作为药物用于治疗乙型肝炎的用途 |
| DK2997019T3 (en) | 2013-05-17 | 2018-12-03 | Janssen Sciences Ireland Uc | SULFAMOYLTHIOPHENAMIDE DERIVATIVES AND USE THEREOF AS MEDICINES FOR TREATING HEPATITIS B |
| JO3603B1 (ar) | 2013-05-17 | 2020-07-05 | Janssen Sciences Ireland Uc | مشتقات سلفامويل بيرولاميد واستخدامها كادوية لمعالجة التهاب الكبد نوع بي |
| WO2014200872A1 (en) | 2013-06-09 | 2014-12-18 | Rjs Biologics Llc | Pharmaceutical compounds targeted by mif affinity-tethered moieties |
| KR102244937B1 (ko) | 2013-07-25 | 2021-04-27 | 얀센 사이언시즈 아일랜드 언리미티드 컴퍼니 | 글리옥사미드 치환된 피롤아미드 유도체 및 ｂ형 간염 치료용 의약으로서의 이의 용도 |
| DK3060547T3 (en) | 2013-10-23 | 2018-01-15 | Janssen Sciences Ireland Uc | CARBOXAMIDE DERIVATIVES AND USE THEREOF AS MEDICINES FOR TREATMENT OF HEPATITS B |
| US9169212B2 (en) | 2014-01-16 | 2015-10-27 | Novira Therapeutics, Inc. | Azepane derivatives and methods of treating hepatitis B infections |
| US10392349B2 (en) | 2014-01-16 | 2019-08-27 | Novira Therapeutics, Inc. | Azepane derivatives and methods of treating hepatitis B infections |
| EP3102225B1 (en) | 2014-02-05 | 2020-03-25 | Novira Therapeutics Inc. | Combination therapy for treatment of hbv infections |
| US11078193B2 (en) | 2014-02-06 | 2021-08-03 | Janssen Sciences Ireland Uc | Sulphamoylpyrrolamide derivatives and the use thereof as medicaments for the treatment of hepatitis B |
| WO2015191677A1 (en) | 2014-06-11 | 2015-12-17 | Incyte Corporation | Bicyclic heteroarylaminoalkyl phenyl derivatives as pi3k inhibitors |
| WO2016020791A1 (en) | 2014-08-05 | 2016-02-11 | Novartis Ag | Ckit antibody drug conjugates |
| PH12017501538B1 (en) | 2015-02-27 | 2024-02-14 | Incyte Holdings Corp | Salts of p13k inhibitor and processes for their preparation |
| US9884831B2 (en) | 2015-03-19 | 2018-02-06 | Novira Therapeutics, Inc. | Azocane and azonane derivatives and methods of treating hepatitis B infections |
| US9732097B2 (en) | 2015-05-11 | 2017-08-15 | Incyte Corporation | Process for the synthesis of a phosphoinositide 3-kinase inhibitor |
| US9988401B2 (en) | 2015-05-11 | 2018-06-05 | Incyte Corporation | Crystalline forms of a PI3K inhibitor |
| US10875876B2 (en) | 2015-07-02 | 2020-12-29 | Janssen Sciences Ireland Uc | Cyclized sulfamoylarylamide derivatives and the use thereof as medicaments for the treatment of hepatitis B |
| TW201718496A (zh) | 2015-09-29 | 2017-06-01 | 諾維拉治療公司 | B型肝炎抗病毒劑之晶型 |
| CN109640980A (zh) | 2016-04-15 | 2019-04-16 | 诺维拉治疗公司 | 包含壳体装配抑制剂的组合和方法 |
| WO2018081361A1 (en) * | 2016-10-28 | 2018-05-03 | Children's Hospital Medical Center | Methods and compositions for treatment of myelodyspastic syndromes and/or acute myleoid leukemias |
| JP2021515769A (ja) | 2018-03-14 | 2021-06-24 | ヤンセン・サイエンシズ・アイルランド・アンリミテッド・カンパニー | カプシド集合調節剤の投薬レジメン |
| CN112469418A (zh) | 2018-06-01 | 2021-03-09 | 因赛特公司 | 治疗pi3k相关病症的给药方案 |
| MA55020A (fr) | 2019-02-22 | 2021-12-29 | Janssen Sciences Ireland Unlimited Co | Dérivés d'amide utiles dans le traitement d'une infection par le virus de l'hépatite b ou de maladies induites par le virus de l'hépatite b |
| AR119732A1 (es) | 2019-05-06 | 2022-01-05 | Janssen Sciences Ireland Unlimited Co | Derivados de amida útiles en el tratamiento de la infección por vhb o de enfermedades inducidas por vhb |
| WO2024099898A1 (en) * | 2022-11-07 | 2024-05-16 | Merck Patent Gmbh | Substituted bi-and tricyclic hset inhibitors |
Family Cites Families (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4235871A (en) | 1978-02-24 | 1980-11-25 | Papahadjopoulos Demetrios P | Method of encapsulating biologically active materials in lipid vesicles |
| US4501728A (en) | 1983-01-06 | 1985-02-26 | Technology Unlimited, Inc. | Masking of liposomes from RES recognition |
| US5023252A (en) | 1985-12-04 | 1991-06-11 | Conrex Pharmaceutical Corporation | Transdermal and trans-membrane delivery of drugs |
| US4837028A (en) | 1986-12-24 | 1989-06-06 | Liposome Technology, Inc. | Liposomes with enhanced circulation time |
| US5011472A (en) | 1988-09-06 | 1991-04-30 | Brown University Research Foundation | Implantable delivery system for biological factors |
| JPH03200961A (ja) * | 1989-10-03 | 1991-09-02 | Fuji Photo Film Co Ltd | ハロゲン化銀カラー写真感光材料 |
| JPH04184433A (ja) * | 1990-11-20 | 1992-07-01 | Fuji Photo Film Co Ltd | ハロゲン化銀カラー写真感光材料 |
| JPH04321046A (ja) * | 1991-02-15 | 1992-11-11 | Fuji Photo Film Co Ltd | ハロゲン化銀カラー写真感光材料の処理方法 |
| US5185450A (en) | 1991-02-19 | 1993-02-09 | University Of South Florida | Tetrazolium compounds for cell viability assays |
| JP2847273B2 (ja) * | 1991-11-22 | 1999-01-13 | 富士写真フイルム株式会社 | カラー画像形成方法 |
| JPH063775A (ja) * | 1992-06-22 | 1994-01-14 | Fuji Photo Film Co Ltd | ハロゲン化銀カラー写真感光材料 |
| US6489300B1 (en) | 1997-07-31 | 2002-12-03 | Eugene D. Thorsett | Carbamyloxy compounds which inhibit leukocyte adhesion mediated by VLA-4 |
| EP1165519A1 (en) | 1999-04-02 | 2002-01-02 | Neurogen Corporation | Aryl and heteroaryl fused aminoalkyl-imidazole derivatives and their use as antidiabetics |
| US6271241B1 (en) * | 1999-04-02 | 2001-08-07 | Neurogen Corporation | Cycloalkyl and aryl fused aminoalkyl-imidazole derivatives: modulators and GLP-1 receptors |
| US6358949B1 (en) | 1999-04-02 | 2002-03-19 | Neurogen Corporation | Aryl and hetroaryl fused aminoalkyl-imidazole derivatives: selective modulators of bradykinin B2 receptors |
| US6545004B1 (en) | 1999-10-27 | 2003-04-08 | Cytokinetics, Inc. | Methods and compositions utilizing quinazolinones |
| DE60028227T2 (de) | 1999-10-27 | 2007-03-29 | Cytokinetics, Inc., South San Francisco | Chinazolinone benutzende verfahren und zusammenstellungen |
| NZ523774A (en) | 2000-08-01 | 2004-09-24 | Sod Conseils Rech Applic | Imidazolyl derivatives |
| AU2001296799A1 (en) | 2000-10-06 | 2002-04-15 | Neurogen Corporation | Benzimidazole and indole derivatives as crf receptor modulators |
| WO2002046168A1 (en) * | 2000-12-07 | 2002-06-13 | Astrazeneca Ab | Therapeutic benzimidazole compounds |
| EP1360180A1 (en) | 2001-01-19 | 2003-11-12 | Cytokinetics, Inc. | Phenothiazine kinesin inhibitors |
| EP1351671A1 (en) | 2001-01-19 | 2003-10-15 | Cytokinetics, Inc. | Triphenylmethane kinesin inhibitors |
| WO2003039460A2 (en) | 2001-11-07 | 2003-05-15 | Merck & Co., Inc. | Mitotic kinesin inhibitors |
| US6753428B2 (en) | 2001-11-20 | 2004-06-22 | Cytokinetics, Inc. | Process for the racemization of chiral quinazolinones |
| DE60222302T2 (de) | 2001-12-06 | 2008-05-29 | Merck & Co., Inc. | Inhibitoren von mitotischem kinesin |
| WO2003049527A2 (en) | 2001-12-06 | 2003-06-19 | Merck & Co., Inc. | Mitotic kinesin inhibitors |
| EP1551812B1 (en) | 2001-12-06 | 2009-03-04 | Merck & Co., Inc. | Mitotic kinesin inhibitors |
| US7244723B2 (en) | 2001-12-06 | 2007-07-17 | Merck & Co., Inc. | Substituted furopyrimidinones as a mitotic kinesin inhibitors |
| EP1481077B1 (en) | 2001-12-06 | 2009-11-04 | Merck & Co., Inc. | Mitotic kinesin inhibitors |
| JP2005532991A (ja) * | 2002-01-10 | 2005-11-04 | ニューロジェン・コーポレーション | メラニン凝集ホルモン受容体リガンド：置換２−（４−ベンジル−ピペラジン−１−イルメチル）−及び２−（４−ベンジル−ジアゼパン−１−イルメチル）−１ｈ−ベンゾイミダゾールアナログ |
| WO2003059289A2 (en) | 2002-01-10 | 2003-07-24 | Neurogen Corporation | Melanin concentrating hormone receptor ligands: substituted benzoimidazole analogues |
| CA2475879A1 (en) | 2002-02-15 | 2003-08-28 | Cytokinetics, Inc. | Synthesis of quinazolinones |
| AU2003249597B2 (en) | 2002-03-08 | 2007-06-28 | Merck Sharp & Dohme Corp. | Mitotic kinesin inhibitors |
| AU2003270015A1 (en) | 2002-05-09 | 2003-12-02 | Cytokinetics, Inc. | Compounds, compositions, and methods |
| WO2003094839A2 (en) | 2002-05-09 | 2003-11-20 | Cytokinetics, Inc. | Pyrimidinone compounds, compositions and methods |
| EP1507534A4 (en) | 2002-05-10 | 2006-11-08 | Cytokinetics Inc | COMPOUNDS, COMPOSITIONS AND METHODS |
| EP1509507A4 (en) | 2002-05-23 | 2006-09-13 | Merck & Co Inc | INHIBITORS OF MITOTIC KINESINE |
| EP1513820A4 (en) | 2002-05-23 | 2006-09-13 | Cytokinetics Inc | COMPOUNDS, COMPOSITIONS AND METHODS |
| PL374190A1 (en) | 2002-06-14 | 2005-10-03 | Merck & Co, Inc. | Mitotic kinesin inhibitors |
| EP1515949B1 (en) | 2002-06-14 | 2007-03-14 | Merck & Co., Inc. | Mitotic kinesin inhibitors |
| JP2005537257A (ja) | 2002-07-08 | 2005-12-08 | メルク エンド カムパニー インコーポレーテッド | 有糸分裂キネシン結合部位 |
| EP1539727B1 (en) | 2002-07-17 | 2009-02-18 | Cytokinetics, Inc. | Compounds, compositions, and methods for treating cellular proliferative diseases |
| EP1537089A4 (en) | 2002-07-23 | 2008-04-16 | Cytokinetics Inc | CONNECTIONS, COMPOSITIONS AND PROCEDURES |
| EP1539180A4 (en) | 2002-08-21 | 2006-08-30 | Cytokinetics Inc | COMPOUNDS, COMPOSITIONS AND METHODS |
| JP2005539062A (ja) | 2002-09-13 | 2005-12-22 | サイトキネティクス・インコーポレーテッド | 化合物、組成物および方法 |
| AU2003900608A0 (en) * | 2003-02-11 | 2003-02-27 | Fujisawa Pharmaceutical Co., Ltd. | Hdac inhibitor |
| CA2526988A1 (en) * | 2003-06-05 | 2005-01-06 | Merck And Co., Inc. | Substituted indoles and a process for preparing substituted indoles |
| JP2007509082A (ja) * | 2003-10-22 | 2007-04-12 | アルピダ エー／エス | ペプチドデホルミラーゼ阻害剤としてのベンゾイミダゾール誘導体類およびそれらの使用 |
| EP1807399A2 (en) | 2004-10-19 | 2007-07-18 | Novartis Vaccines and Diagnostics, Inc. | Indole and benzimidazole derivatives |
-
2005
- 2005-10-14 EP EP05851219A patent/EP1807399A2/en not_active Withdrawn
- 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 US US11/665,956 patent/US8008335B2/en not_active Expired - Fee Related
- 2005-10-14 CA CA002584979A patent/CA2584979A1/en not_active Abandoned
- 2005-10-14 JP JP2007537929A patent/JP2008517057A/ja active Pending
- 2005-10-14 AU AU2005301133A patent/AU2005301133A1/en not_active Abandoned
- 2005-10-14 MX MX2007004699A patent/MX2007004699A/es not_active Application Discontinuation
- 2005-10-14 EP EP10181182A patent/EP2275412A1/en not_active Withdrawn
- 2005-10-14 RU RU2007118523/04A patent/RU2007118523A/ru not_active Application Discontinuation
- 2005-10-14 BR BRPI0517314-0A patent/BRPI0517314A/pt not_active IP Right Cessation
- 2005-10-14 CN CNA2005800402742A patent/CN101233115A/zh active Pending
- 2005-10-14 WO PCT/US2005/036803 patent/WO2006049835A2/en not_active Ceased