RU2427572C2 - N-(1-(1-бензил-4-фенил-1н-имидазол-2-ил)-2,2-диметилпропил)бензамидные производные и родственные соединения в качестве ингибиторов кинезинового белка веретена (ksp) для лечения рака - Google Patents
N-(1-(1-бензил-4-фенил-1н-имидазол-2-ил)-2,2-диметилпропил)бензамидные производные и родственные соединения в качестве ингибиторов кинезинового белка веретена (ksp) для лечения рака Download PDFInfo
- Publication number
- RU2427572C2 RU2427572C2 RU2007101612/04A RU2007101612A RU2427572C2 RU 2427572 C2 RU2427572 C2 RU 2427572C2 RU 2007101612/04 A RU2007101612/04 A RU 2007101612/04A RU 2007101612 A RU2007101612 A RU 2007101612A RU 2427572 C2 RU2427572 C2 RU 2427572C2
- Authority
- RU
- Russia
- Prior art keywords
- imidazol
- benzyl
- dimethylpropyl
- phenyl
- amino
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract 32
- 102000010638 Kinesin Human genes 0.000 title claims abstract 3
- 108010063296 Kinesin Proteins 0.000 title claims abstract 3
- 206010028980 Neoplasm Diseases 0.000 title claims abstract 3
- 201000011510 cancer Diseases 0.000 title claims abstract 3
- 239000003112 inhibitor Substances 0.000 title 1
- KTVLPYPWRBPIAZ-UHFFFAOYSA-N n-[1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]benzamide Chemical class N=1C(C=2C=CC=CC=2)=CN(CC=2C=CC=CC=2)C=1C(C(C)(C)C)NC(=O)C1=CC=CC=C1 KTVLPYPWRBPIAZ-UHFFFAOYSA-N 0.000 title 1
- 102000004169 proteins and genes Human genes 0.000 title 1
- 108090000623 proteins and genes Proteins 0.000 title 1
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 61
- 125000000217 alkyl group Chemical group 0.000 claims abstract 47
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 39
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 35
- 239000001257 hydrogen Substances 0.000 claims abstract 35
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract 27
- 229910052736 halogen Inorganic materials 0.000 claims abstract 25
- 150000002367 halogens Chemical class 0.000 claims abstract 25
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 24
- 125000002947 alkylene group Chemical group 0.000 claims abstract 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 18
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract 18
- 125000003118 aryl group Chemical group 0.000 claims abstract 16
- 125000005415 substituted alkoxy group Chemical group 0.000 claims abstract 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 11
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 10
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 10
- 125000004104 aryloxy group Chemical group 0.000 claims abstract 8
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims abstract 8
- 229910052799 carbon Inorganic materials 0.000 claims abstract 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 6
- 150000001721 carbon Chemical group 0.000 claims abstract 5
- 150000003839 salts Chemical class 0.000 claims abstract 5
- 125000000266 alpha-aminoacyl group Chemical group 0.000 claims abstract 4
- 150000001412 amines Chemical class 0.000 claims abstract 3
- 230000002401 inhibitory effect Effects 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims abstract 3
- 125000006833 (C1-C5) alkylene group Chemical group 0.000 claims abstract 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract 2
- 230000000694 effects Effects 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 2
- -1 amino, substituted amino Chemical group 0.000 claims 253
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims 76
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 27
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 25
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 20
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 17
- 125000001424 substituent group Chemical group 0.000 claims 14
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 13
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 10
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 9
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims 9
- UJJLJRQIPMGXEZ-BYPYZUCNSA-N (2s)-oxolane-2-carboxylic acid Chemical compound OC(=O)[C@@H]1CCCO1 UJJLJRQIPMGXEZ-BYPYZUCNSA-N 0.000 claims 7
- 125000003564 m-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(C#N)=C1[H])C([H])([H])* 0.000 claims 7
- 239000010802 sludge Substances 0.000 claims 7
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical group [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 6
- 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 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 4
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 3
- 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims 3
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 229910052760 oxygen Chemical group 0.000 claims 3
- 239000001301 oxygen Chemical group 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 239000011593 sulfur Chemical group 0.000 claims 3
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[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
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 2
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims 2
- LSUFQWSIEAGXTH-IBGZPJMESA-N (1r)-1-[1-benzyl-4-(2,5-difluorophenyl)imidazol-2-yl]-2,2-dimethylpropan-1-amine Chemical compound CC(C)(C)[C@@H](N)C1=NC(C=2C(=CC=C(F)C=2)F)=CN1CC1=CC=CC=C1 LSUFQWSIEAGXTH-IBGZPJMESA-N 0.000 claims 1
- FVCKIQOXSCWFMB-XCZPVHLTSA-N (2s)-2-amino-4-[benzoyl-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]amino]butanoic acid Chemical compound OC(=O)[C@@H](N)CCN([C@H](C(C)(C)C)C=1N(C=C(N=1)C=1C=CC=CC=1)CC=1C=CC=CC=1)C(=O)C1=CC=CC=C1 FVCKIQOXSCWFMB-XCZPVHLTSA-N 0.000 claims 1
- BUCIHQBAZBVIIG-WNCULLNHSA-N (5r)-3-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-1-oxa-3,7-diazaspiro[4.4]nonan-2-one Chemical compound O1C(=O)N([C@H](C(C)(C)C)C=2N(C=C(N=2)C=2C=CC=CC=2)CC=2C=CC=CC=2)C[C@@]21CCNC2 BUCIHQBAZBVIIG-WNCULLNHSA-N 0.000 claims 1
- UXXGZJSTKVFYBP-LBNVMWSVSA-N (5r)-9-[(1r)-1-[4-(3-fluorophenyl)-1-[(3-fluorophenyl)methyl]imidazol-2-yl]-2,2-dimethylpropyl]-6-oxa-2,9-diazaspiro[4.5]decan-8-one Chemical compound O1CC(=O)N([C@H](C(C)(C)C)C=2N(C=C(N=2)C=2C=C(F)C=CC=2)CC=2C=C(F)C=CC=2)C[C@@]21CCNC2 UXXGZJSTKVFYBP-LBNVMWSVSA-N 0.000 claims 1
- BUCIHQBAZBVIIG-HOFKKMOUSA-N (5s)-3-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-1-oxa-3,7-diazaspiro[4.4]nonan-2-one Chemical compound O1C(=O)N([C@H](C(C)(C)C)C=2N(C=C(N=2)C=2C=CC=CC=2)CC=2C=CC=CC=2)C[C@]21CCNC2 BUCIHQBAZBVIIG-HOFKKMOUSA-N 0.000 claims 1
- 125000001359 1,2,3-triazol-4-yl group Chemical group [H]N1N=NC([*])=C1[H] 0.000 claims 1
- 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 claims 1
- DZKGCEKADYNCKC-UHFFFAOYSA-N 1-(2-amino-1-phenylethyl)-6-(1-benzyl-4-phenylimidazol-2-yl)piperidin-2-one Chemical compound C=1C=CC=CC=1C(CN)N(C(CCC1)=O)C1C1=NC(C=2C=CC=CC=2)=CN1CC1=CC=CC=C1 DZKGCEKADYNCKC-UHFFFAOYSA-N 0.000 claims 1
- MCVXMVFHWASHSU-QHCPKHFHSA-N 1-[2-[[(1R)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]amino]ethyl]cyclopropan-1-amine Chemical compound N([C@H](C(C)(C)C)C=1N(C=C(N=1)C=1C=CC=CC=1)CC=1C=CC=CC=1)CCC1(N)CC1 MCVXMVFHWASHSU-QHCPKHFHSA-N 0.000 claims 1
- LZPCOLGNVXYJMS-UHFFFAOYSA-N 1-benzyl-6-(1-benzyl-4-phenylimidazol-2-yl)piperidin-2-one Chemical compound O=C1CCCC(C=2N(C=C(N=2)C=2C=CC=CC=2)CC=2C=CC=CC=2)N1CC1=CC=CC=C1 LZPCOLGNVXYJMS-UHFFFAOYSA-N 0.000 claims 1
- KVUIKEFIXATPAO-UHFFFAOYSA-N 1-benzyl-6-[1-[(3-chlorophenyl)methyl]-4-phenylimidazol-2-yl]piperidin-2-one Chemical compound ClC1=CC=CC(CN2C(=NC(=C2)C=2C=CC=CC=2)C2N(C(=O)CCC2)CC=2C=CC=CC=2)=C1 KVUIKEFIXATPAO-UHFFFAOYSA-N 0.000 claims 1
- OHCSTNUNQFZQJN-UHFFFAOYSA-N 1-oxa-3,7-diazaspiro[4.4]nonan-2-one Chemical compound O1C(=O)NCC11CNCC1 OHCSTNUNQFZQJN-UHFFFAOYSA-N 0.000 claims 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- PDQRQJVPEFGVRK-UHFFFAOYSA-N 2,1,3-benzothiadiazole Chemical compound C1=CC=CC2=NSN=C21 PDQRQJVPEFGVRK-UHFFFAOYSA-N 0.000 claims 1
- 125000004463 2,4-dimethyl-thiazol-5-yl group Chemical group CC=1SC(=C(N1)C)* 0.000 claims 1
- IPVAAFZDSBFGFY-PMERELPUSA-N 2-[3-[benzoyl-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]amino]propylamino]acetic acid Chemical compound OC(=O)CNCCCN([C@H](C(C)(C)C)C=1N(C=C(N=1)C=1C=CC=CC=1)CC=1C=CC=CC=1)C(=O)C1=CC=CC=C1 IPVAAFZDSBFGFY-PMERELPUSA-N 0.000 claims 1
- HTUMNAXNANBKGF-QHCPKHFHSA-N 2-[[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-butylamino]-2-oxoacetic acid Chemical compound CCCCN(C(=O)C(O)=O)[C@H](C(C)(C)C)C1=NC(C=2C=CC=CC=2)=CN1CC1=CC=CC=C1 HTUMNAXNANBKGF-QHCPKHFHSA-N 0.000 claims 1
- JHRBKLWZJWGCHP-QFIPXVFZSA-N 2-[[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-propylamino]-2-oxoacetic acid Chemical compound CCCN(C(=O)C(O)=O)[C@H](C(C)(C)C)C1=NC(C=2C=CC=CC=2)=CN1CC1=CC=CC=C1 JHRBKLWZJWGCHP-QFIPXVFZSA-N 0.000 claims 1
- PNTSJKCQAUUFTO-XMMPIXPASA-N 2-amino-n-(3-aminopropyl)-n-[(1r)-1-[1-benzyl-4-(3-chlorophenyl)imidazol-2-yl]-2-methylpropyl]-1,3-thiazole-4-carboxamide Chemical compound NCCCN([C@H](C(C)C)C=1N(C=C(N=1)C=1C=C(Cl)C=CC=1)CC=1C=CC=CC=1)C(=O)C1=CSC(N)=N1 PNTSJKCQAUUFTO-XMMPIXPASA-N 0.000 claims 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 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
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 1
- 125000006288 3,5-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(C([H])=C1F)C([H])([H])* 0.000 claims 1
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 1
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- NSSJRNVXBAPWFE-UHFFFAOYSA-N 4-chloro-1,3-dimethyl-2h-pyrazolo[4,3-b]pyridine Chemical group ClN1C=CC=C2N(C)NC(C)=C21 NSSJRNVXBAPWFE-UHFFFAOYSA-N 0.000 claims 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- 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 1
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- ZKAVAJBOYWXIHK-UHFFFAOYSA-N 6-(1-benzyl-4-phenylimidazol-2-yl)piperidin-2-one Chemical compound N1C(=O)CCCC1C1=NC(C=2C=CC=CC=2)=CN1CC1=CC=CC=C1 ZKAVAJBOYWXIHK-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- HOKWSUFBGZJTQK-QEXBQMGZSA-N CC(C)(C)[C@H](C1=NC(C(C=C(C=C2)F)=C2F)=CN1CC1=CC=CC=C1)NCCCN.OC([C@H]1OCCC1)=O Chemical compound CC(C)(C)[C@H](C1=NC(C(C=C(C=C2)F)=C2F)=CN1CC1=CC=CC=C1)NCCCN.OC([C@H]1OCCC1)=O HOKWSUFBGZJTQK-QEXBQMGZSA-N 0.000 claims 1
- VQLJRJZHRMPXCF-OEJWQSAISA-N CC(C)(C)[C@H](C1=NC(C2=CC(F)=CC=C2)=CN1CC1=CC=CC=C1)NCCC1(CC1)N.OC([C@H]1OCCC1)=O Chemical compound CC(C)(C)[C@H](C1=NC(C2=CC(F)=CC=C2)=CN1CC1=CC=CC=C1)NCCC1(CC1)N.OC([C@H]1OCCC1)=O VQLJRJZHRMPXCF-OEJWQSAISA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- PNCLQKIBACWDSW-AREMUKBSSA-N N-[(1R)-2-methyl-1-[1-[(2-methylphenyl)methyl]-4-phenylimidazol-2-yl]propyl]benzamide Chemical compound C(C1=CC=CC=C1)(=O)N[C@H](C(C)C)C=1N(C=C(N=1)C1=CC=CC=C1)CC1=C(C=CC=C1)C PNCLQKIBACWDSW-AREMUKBSSA-N 0.000 claims 1
- CSYOSKFKPGTZJE-DCWQJPKNSA-N [(2R)-2-(1-benzyl-4-phenylimidazol-2-yl)-5-(methylamino)pyrrolidin-1-yl]-phenylmethanone Chemical compound C(C1=CC=CC=C1)(=O)N1C(CC[C@@H]1C=1N(C=C(N=1)C1=CC=CC=C1)CC1=CC=CC=C1)NC CSYOSKFKPGTZJE-DCWQJPKNSA-N 0.000 claims 1
- MLXXCNSKSSIWNL-YTTGMZPUSA-N [3-[benzoyl-[(1R)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]amino]propyl-ethylamino] acetate Chemical compound C(C)(=O)ON(CCCN([C@H](C(C)(C)C)C=1N(C=C(N=1)C1=CC=CC=C1)CC1=CC=CC=C1)C(C1=CC=CC=C1)=O)CC MLXXCNSKSSIWNL-YTTGMZPUSA-N 0.000 claims 1
- UDEWPOVQBGFNGE-UHFFFAOYSA-N benzoic acid n-propyl ester Natural products CCCOC(=O)C1=CC=CC=C1 UDEWPOVQBGFNGE-UHFFFAOYSA-N 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 150000001733 carboxylic acid esters Chemical class 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims 1
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 1
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 claims 1
- 125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 claims 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- WTISLDWKTRJBFH-DEOSSOPVSA-N methyl n-[2-(1-aminocyclopropyl)ethyl]-n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]carbamate Chemical compound COC(=O)N([C@@H](C=1N(C=C(N=1)C=1C=CC=CC=1)CC=1C=CC=CC=1)C(C)(C)C)CCC1(N)CC1 WTISLDWKTRJBFH-DEOSSOPVSA-N 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims 1
- OELBZMMCOUHSNC-QPPBQGQZSA-N n'-[(2r)-2-(aminomethyl)-3-hydroxypropyl]-n'-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-n-methyloxamide Chemical compound CNC(=O)C(=O)N(C[C@@H](CN)CO)[C@H](C(C)(C)C)C1=NC(C=2C=CC=CC=2)=CN1CC1=CC=CC=C1 OELBZMMCOUHSNC-QPPBQGQZSA-N 0.000 claims 1
- OELBZMMCOUHSNC-URXFXBBRSA-N n'-[(2s)-2-(aminomethyl)-3-hydroxypropyl]-n'-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-n-methyloxamide Chemical compound CNC(=O)C(=O)N(C[C@H](CN)CO)[C@H](C(C)(C)C)C1=NC(C=2C=CC=CC=2)=CN1CC1=CC=CC=C1 OELBZMMCOUHSNC-URXFXBBRSA-N 0.000 claims 1
- TYKUBRGCTAMIOI-MUUNZHRXSA-N n-(2-aminoethyl)-n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2-methylpropyl]-4-methylbenzamide Chemical compound NCCN([C@H](C(C)C)C=1N(C=C(N=1)C=1C=CC=CC=1)CC=1C=CC=CC=1)C(=O)C1=CC=C(C)C=C1 TYKUBRGCTAMIOI-MUUNZHRXSA-N 0.000 claims 1
- GNAIVSIMEUVFSI-SANMLTNESA-N n-(3-amino-3-methylbutyl)-n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound COCC(=O)N(CCC(C)(C)N)[C@H](C(C)(C)C)C1=NC(C=2C=CC=CC=2)=CN1CC1=CC=CC=C1 GNAIVSIMEUVFSI-SANMLTNESA-N 0.000 claims 1
- UHEYWHYOJQLPCL-UHFFFAOYSA-N n-(3-amino-4-fluorobutyl)-n-[2-[4-(3-fluorophenyl)-1-[(3-fluorophenyl)methyl]imidazol-2-yl]propan-2-yl]-2-methoxyacetamide Chemical compound FCC(N)CCN(C(=O)COC)C(C)(C)C1=NC(C=2C=C(F)C=CC=2)=CN1CC1=CC=CC(F)=C1 UHEYWHYOJQLPCL-UHFFFAOYSA-N 0.000 claims 1
- FEMXNGOSHRKIGQ-MHZLTWQESA-N n-(3-aminopropyl)-n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-1,5-dimethylpyrazole-3-carboxamide Chemical compound CN1C(C)=CC(C(=O)N(CCCN)[C@@H](C=2N(C=C(N=2)C=2C=CC=CC=2)CC=2C=CC=CC=2)C(C)(C)C)=N1 FEMXNGOSHRKIGQ-MHZLTWQESA-N 0.000 claims 1
- BBUFPVQIZGZIAV-VWLOTQADSA-N n-(3-aminopropyl)-n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-2-cyanoacetamide Chemical compound NCCCN(C(=O)CC#N)[C@H](C(C)(C)C)C1=NC(C=2C=CC=CC=2)=CN1CC1=CC=CC=C1 BBUFPVQIZGZIAV-VWLOTQADSA-N 0.000 claims 1
- MRPVIBDJIOTRHN-SANMLTNESA-N n-(3-aminopropyl)-n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-2-ethoxyacetamide Chemical compound CCOCC(=O)N(CCCN)[C@H](C(C)(C)C)C1=NC(C=2C=CC=CC=2)=CN1CC1=CC=CC=C1 MRPVIBDJIOTRHN-SANMLTNESA-N 0.000 claims 1
- YLPUPVUMNFYUKK-DEOSSOPVSA-N n-(3-aminopropyl)-n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-2-hydroxyacetamide Chemical compound NCCCN(C(=O)CO)[C@H](C(C)(C)C)C1=NC(C=2C=CC=CC=2)=CN1CC1=CC=CC=C1 YLPUPVUMNFYUKK-DEOSSOPVSA-N 0.000 claims 1
- MDZXGVCSJQTFQS-VWLOTQADSA-N n-(3-aminopropyl)-n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound COCC(=O)N(CCCN)[C@H](C(C)(C)C)C1=NC(C=2C=CC=CC=2)=CN1CC1=CC=CC=C1 MDZXGVCSJQTFQS-VWLOTQADSA-N 0.000 claims 1
- VCYQIRARGBETTP-LJAQVGFWSA-N n-(3-aminopropyl)-n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-4-methylbenzamide Chemical compound C1=CC(C)=CC=C1C(=O)N(CCCN)[C@H](C(C)(C)C)C1=NC(C=2C=CC=CC=2)=CN1CC1=CC=CC=C1 VCYQIRARGBETTP-LJAQVGFWSA-N 0.000 claims 1
- IRHQPNWCLFEHOD-NDEPHWFRSA-N n-(3-aminopropyl)-n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-6-methylpyridine-3-carboxamide Chemical compound C1=NC(C)=CC=C1C(=O)N(CCCN)[C@H](C(C)(C)C)C1=NC(C=2C=CC=CC=2)=CN1CC1=CC=CC=C1 IRHQPNWCLFEHOD-NDEPHWFRSA-N 0.000 claims 1
- IRPKBEFYAJTFJA-HHHXNRCGSA-N n-(3-aminopropyl)-n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2-methylpropyl]-1,5-dimethylpyrazole-3-carboxamide Chemical compound NCCCN([C@H](C(C)C)C=1N(C=C(N=1)C=1C=CC=CC=1)CC=1C=CC=CC=1)C(=O)C=1C=C(C)N(C)N=1 IRPKBEFYAJTFJA-HHHXNRCGSA-N 0.000 claims 1
- NWSQACVSCHVQJT-GDLZYMKVSA-N n-(3-aminopropyl)-n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2-methylpropyl]-4-methylbenzamide Chemical compound NCCCN([C@H](C(C)C)C=1N(C=C(N=1)C=1C=CC=CC=1)CC=1C=CC=CC=1)C(=O)C1=CC=C(C)C=C1 NWSQACVSCHVQJT-GDLZYMKVSA-N 0.000 claims 1
- GZJHGIRLCZFFHZ-SSEXGKCCSA-N n-(3-aminopropyl)-n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-3-methylbutyl]-4-methylbenzamide Chemical compound NCCCN([C@H](CC(C)C)C=1N(C=C(N=1)C=1C=CC=CC=1)CC=1C=CC=CC=1)C(=O)C1=CC=C(C)C=C1 GZJHGIRLCZFFHZ-SSEXGKCCSA-N 0.000 claims 1
- PCZREWRIRMITAF-MHZLTWQESA-N n-(3-aminopropyl)-n-[(1r)-1-(1-benzyl-4-pyridin-2-ylimidazol-2-yl)-2,2-dimethylpropyl]-2,4-difluorobenzamide Chemical compound NCCCN([C@H](C(C)(C)C)C=1N(C=C(N=1)C=1N=CC=CC=1)CC=1C=CC=CC=1)C(=O)C1=CC=C(F)C=C1F PCZREWRIRMITAF-MHZLTWQESA-N 0.000 claims 1
- VITGBVNXSYHSOS-NDEPHWFRSA-N n-(3-aminopropyl)-n-[(1r)-1-(1-benzyl-4-pyridin-2-ylimidazol-2-yl)-2,2-dimethylpropyl]-4-methylbenzamide Chemical compound C1=CC(C)=CC=C1C(=O)N(CCCN)[C@H](C(C)(C)C)C1=NC(C=2N=CC=CC=2)=CN1CC1=CC=CC=C1 VITGBVNXSYHSOS-NDEPHWFRSA-N 0.000 claims 1
- AXTVPRRAOBCZBL-SANMLTNESA-N n-(3-aminopropyl)-n-[(1r)-1-(1-benzyl-4-pyridin-2-ylimidazol-2-yl)-2,2-dimethylpropyl]-6-chloropyridine-3-carboxamide Chemical compound NCCCN([C@H](C(C)(C)C)C=1N(C=C(N=1)C=1N=CC=CC=1)CC=1C=CC=CC=1)C(=O)C1=CC=C(Cl)N=C1 AXTVPRRAOBCZBL-SANMLTNESA-N 0.000 claims 1
- HFWCSECZRIAFAQ-GDLZYMKVSA-N n-(3-aminopropyl)-n-[(1r)-1-(1-benzyl-5-methyl-4-phenylimidazol-2-yl)-2-methylpropyl]-2,4-difluorobenzamide Chemical compound NCCCN([C@H](C(C)C)C=1N(C(C)=C(N=1)C=1C=CC=CC=1)CC=1C=CC=CC=1)C(=O)C1=CC=C(F)C=C1F HFWCSECZRIAFAQ-GDLZYMKVSA-N 0.000 claims 1
- XDWLCVWBGYGDLU-SSEXGKCCSA-N n-(3-aminopropyl)-n-[(1r)-1-(1-benzyl-5-methyl-4-phenylimidazol-2-yl)-2-methylpropyl]-4-methylbenzamide Chemical compound NCCCN([C@H](C(C)C)C=1N(C(C)=C(N=1)C=1C=CC=CC=1)CC=1C=CC=CC=1)C(=O)C1=CC=C(C)C=C1 XDWLCVWBGYGDLU-SSEXGKCCSA-N 0.000 claims 1
- RSBREJSOQHUBFF-MUUNZHRXSA-N n-(3-aminopropyl)-n-[(1r)-1-(1-benzyl-5-methyl-4-phenylimidazol-2-yl)-2-methylpropyl]-6-chloropyridine-3-carboxamide Chemical compound NCCCN([C@H](C(C)C)C=1N(C(C)=C(N=1)C=1C=CC=CC=1)CC=1C=CC=CC=1)C(=O)C1=CC=C(Cl)N=C1 RSBREJSOQHUBFF-MUUNZHRXSA-N 0.000 claims 1
- MFNCKNAMGQKWNK-GDLZYMKVSA-N n-(3-aminopropyl)-n-[(1r)-1-[1-[(3,5-difluorophenyl)methyl]-4-phenylimidazol-2-yl]-2-methylpropyl]-4-methylbenzamide Chemical compound NCCCN([C@H](C(C)C)C=1N(C=C(N=1)C=1C=CC=CC=1)CC=1C=C(F)C=C(F)C=1)C(=O)C1=CC=C(C)C=C1 MFNCKNAMGQKWNK-GDLZYMKVSA-N 0.000 claims 1
- VSDWTJAGTCLVIB-NDEPHWFRSA-N n-(3-aminopropyl)-n-[(1r)-1-[1-[(3-cyanophenyl)methyl]-4-phenylimidazol-2-yl]-2,2-dimethylpropyl]-1,5-dimethylpyrazole-3-carboxamide Chemical compound CN1C(C)=CC(C(=O)N(CCCN)[C@@H](C=2N(C=C(N=2)C=2C=CC=CC=2)CC=2C=C(C=CC=2)C#N)C(C)(C)C)=N1 VSDWTJAGTCLVIB-NDEPHWFRSA-N 0.000 claims 1
- OXKTXOWQWXRDRK-SANMLTNESA-N n-(3-aminopropyl)-n-[(1r)-1-[1-[(3-cyanophenyl)methyl]-4-phenylimidazol-2-yl]-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound COCC(=O)N(CCCN)[C@H](C(C)(C)C)C1=NC(C=2C=CC=CC=2)=CN1CC1=CC=CC(C#N)=C1 OXKTXOWQWXRDRK-SANMLTNESA-N 0.000 claims 1
- HDBQEPMHRWMLFK-NDEPHWFRSA-N n-(3-aminopropyl)-n-[(1r)-1-[1-[(3-methoxyphenyl)methyl]-4-phenylimidazol-2-yl]-2,2-dimethylpropyl]-1,5-dimethylpyrazole-3-carboxamide Chemical compound COC1=CC=CC(CN2C(=NC(=C2)C=2C=CC=CC=2)[C@H](N(CCCN)C(=O)C2=NN(C)C(C)=C2)C(C)(C)C)=C1 HDBQEPMHRWMLFK-NDEPHWFRSA-N 0.000 claims 1
- IJHXWPJXPKXZKH-VWLOTQADSA-N n-(3-aminopropyl)-n-[(1r)-1-[1-benzyl-4-(2,5-difluorophenyl)imidazol-2-yl]-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound COCC(=O)N(CCCN)[C@H](C(C)(C)C)C1=NC(C=2C(=CC=C(F)C=2)F)=CN1CC1=CC=CC=C1 IJHXWPJXPKXZKH-VWLOTQADSA-N 0.000 claims 1
- BUUPVVZEBZIBHW-VWLOTQADSA-N n-(3-aminopropyl)-n-[(1r)-1-[1-benzyl-4-(2,5-difluorophenyl)imidazol-2-yl]-2,2-dimethylpropyl]-2-methylsulfonylacetamide Chemical compound NCCCN(C(=O)CS(C)(=O)=O)[C@H](C(C)(C)C)C1=NC(C=2C(=CC=C(F)C=2)F)=CN1CC1=CC=CC=C1 BUUPVVZEBZIBHW-VWLOTQADSA-N 0.000 claims 1
- IPKXJCJMAQWWIL-MUUNZHRXSA-N n-(3-aminopropyl)-n-[(1r)-1-[1-benzyl-4-(3-bromophenyl)imidazol-2-yl]-2-methylpropyl]-2,4-difluorobenzamide Chemical compound NCCCN([C@H](C(C)C)C=1N(C=C(N=1)C=1C=C(Br)C=CC=1)CC=1C=CC=CC=1)C(=O)C1=CC=C(F)C=C1F IPKXJCJMAQWWIL-MUUNZHRXSA-N 0.000 claims 1
- XDUIBSXHCDLWKP-GDLZYMKVSA-N n-(3-aminopropyl)-n-[(1r)-1-[1-benzyl-4-(3-bromophenyl)imidazol-2-yl]-2-methylpropyl]-4-methylbenzamide Chemical compound NCCCN([C@H](C(C)C)C=1N(C=C(N=1)C=1C=C(Br)C=CC=1)CC=1C=CC=CC=1)C(=O)C1=CC=C(C)C=C1 XDUIBSXHCDLWKP-GDLZYMKVSA-N 0.000 claims 1
- FLQVTRFRXBXCNB-LJAQVGFWSA-N n-(3-aminopropyl)-n-[(1r)-1-[1-benzyl-4-(3-chlorophenyl)imidazol-2-yl]-2,2-dimethylpropyl]-4-methylbenzamide Chemical compound C1=CC(C)=CC=C1C(=O)N(CCCN)[C@H](C(C)(C)C)C1=NC(C=2C=C(Cl)C=CC=2)=CN1CC1=CC=CC=C1 FLQVTRFRXBXCNB-LJAQVGFWSA-N 0.000 claims 1
- BNEHJHOTMIKQSS-MHZLTWQESA-N n-(3-aminopropyl)-n-[(1r)-1-[1-benzyl-4-(3-chlorophenyl)imidazol-2-yl]-2,2-dimethylpropyl]-6-chloropyridine-3-carboxamide Chemical compound NCCCN([C@H](C(C)(C)C)C=1N(C=C(N=1)C=1C=C(Cl)C=CC=1)CC=1C=CC=CC=1)C(=O)C1=CC=C(Cl)N=C1 BNEHJHOTMIKQSS-MHZLTWQESA-N 0.000 claims 1
- MUVPYYGNFXYIHX-RUZDIDTESA-N n-(3-aminopropyl)-n-[(1r)-1-[1-benzyl-4-(3-chlorophenyl)imidazol-2-yl]-2-methylpropyl]-1,3-thiazole-4-carboxamide Chemical compound NCCCN([C@H](C(C)C)C=1N(C=C(N=1)C=1C=C(Cl)C=CC=1)CC=1C=CC=CC=1)C(=O)C1=CSC=N1 MUVPYYGNFXYIHX-RUZDIDTESA-N 0.000 claims 1
- DDDJLBPWWYGLEH-HHHXNRCGSA-N n-(3-aminopropyl)-n-[(1r)-1-[1-benzyl-4-(3-chlorophenyl)imidazol-2-yl]-2-methylpropyl]-1,5-dimethylpyrazole-3-carboxamide Chemical compound NCCCN([C@H](C(C)C)C=1N(C=C(N=1)C=1C=C(Cl)C=CC=1)CC=1C=CC=CC=1)C(=O)C=1C=C(C)N(C)N=1 DDDJLBPWWYGLEH-HHHXNRCGSA-N 0.000 claims 1
- QBTMENJCJLFDPY-RUZDIDTESA-N n-(3-aminopropyl)-n-[(1r)-1-[1-benzyl-4-(3-chlorophenyl)imidazol-2-yl]-2-methylpropyl]-1-methyl-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound NCCCN([C@H](C(C)C)C=1N(C=C(N=1)C=1C=C(Cl)C=CC=1)CC=1C=CC=CC=1)C(=O)C1=CN(C)N=C1C(F)(F)F QBTMENJCJLFDPY-RUZDIDTESA-N 0.000 claims 1
- LZLHOLXIVCDLFX-MUUNZHRXSA-N n-(3-aminopropyl)-n-[(1r)-1-[1-benzyl-4-(3-chlorophenyl)imidazol-2-yl]-2-methylpropyl]-2,1,3-benzothiadiazole-4-carboxamide Chemical compound C1([C@H](N(CCCN)C(=O)C=2C3=NSN=C3C=CC=2)C(C)C)=NC(C=2C=C(Cl)C=CC=2)=CN1CC1=CC=CC=C1 LZLHOLXIVCDLFX-MUUNZHRXSA-N 0.000 claims 1
- LWCYJCOLPLVBLZ-MUUNZHRXSA-N n-(3-aminopropyl)-n-[(1r)-1-[1-benzyl-4-(3-chlorophenyl)imidazol-2-yl]-2-methylpropyl]-2,4-difluorobenzamide Chemical compound NCCCN([C@H](C(C)C)C=1N(C=C(N=1)C=1C=C(Cl)C=CC=1)CC=1C=CC=CC=1)C(=O)C1=CC=C(F)C=C1F LWCYJCOLPLVBLZ-MUUNZHRXSA-N 0.000 claims 1
- QBYSQPKYQNZUEZ-AREMUKBSSA-N n-(3-aminopropyl)-n-[(1r)-1-[1-benzyl-4-(3-chlorophenyl)imidazol-2-yl]-2-methylpropyl]-2,4-dimethyl-1,3-thiazole-5-carboxamide Chemical compound NCCCN([C@H](C(C)C)C=1N(C=C(N=1)C=1C=C(Cl)C=CC=1)CC=1C=CC=CC=1)C(=O)C=1SC(C)=NC=1C QBYSQPKYQNZUEZ-AREMUKBSSA-N 0.000 claims 1
- IGRDAXWVGVWFMX-MUUNZHRXSA-N n-(3-aminopropyl)-n-[(1r)-1-[1-benzyl-4-(3-chlorophenyl)imidazol-2-yl]-2-methylpropyl]-2-chloro-6-methylpyridine-4-carboxamide Chemical compound NCCCN([C@H](C(C)C)C=1N(C=C(N=1)C=1C=C(Cl)C=CC=1)CC=1C=CC=CC=1)C(=O)C1=CC(C)=NC(Cl)=C1 IGRDAXWVGVWFMX-MUUNZHRXSA-N 0.000 claims 1
- LQMXQFZRCHTLOJ-MUUNZHRXSA-N n-(3-aminopropyl)-n-[(1r)-1-[1-benzyl-4-(3-chlorophenyl)imidazol-2-yl]-2-methylpropyl]-2-chlorobenzamide Chemical compound NCCCN([C@H](C(C)C)C=1N(C=C(N=1)C=1C=C(Cl)C=CC=1)CC=1C=CC=CC=1)C(=O)C1=CC=CC=C1Cl LQMXQFZRCHTLOJ-MUUNZHRXSA-N 0.000 claims 1
- RMYILWAPKNVWMP-MUUNZHRXSA-N n-(3-aminopropyl)-n-[(1r)-1-[1-benzyl-4-(3-chlorophenyl)imidazol-2-yl]-2-methylpropyl]-2-ethyl-5-methylpyrazole-3-carboxamide Chemical compound CCN1N=C(C)C=C1C(=O)N(CCCN)[C@H](C(C)C)C1=NC(C=2C=C(Cl)C=CC=2)=CN1CC1=CC=CC=C1 RMYILWAPKNVWMP-MUUNZHRXSA-N 0.000 claims 1
- XIIFXWOKPLOZQA-RUZDIDTESA-N n-(3-aminopropyl)-n-[(1r)-1-[1-benzyl-4-(3-chlorophenyl)imidazol-2-yl]-2-methylpropyl]-2-methoxyacetamide Chemical compound COCC(=O)N(CCCN)[C@H](C(C)C)C1=NC(C=2C=C(Cl)C=CC=2)=CN1CC1=CC=CC=C1 XIIFXWOKPLOZQA-RUZDIDTESA-N 0.000 claims 1
- HVMQMZQWLWMUOK-GDLZYMKVSA-N n-(3-aminopropyl)-n-[(1r)-1-[1-benzyl-4-(3-chlorophenyl)imidazol-2-yl]-2-methylpropyl]-2-methoxybenzamide Chemical compound COC1=CC=CC=C1C(=O)N(CCCN)[C@H](C(C)C)C1=NC(C=2C=C(Cl)C=CC=2)=CN1CC1=CC=CC=C1 HVMQMZQWLWMUOK-GDLZYMKVSA-N 0.000 claims 1
- IMDUNOBXMILGCH-MUUNZHRXSA-N n-(3-aminopropyl)-n-[(1r)-1-[1-benzyl-4-(3-chlorophenyl)imidazol-2-yl]-2-methylpropyl]-3,4-dichlorobenzamide Chemical compound NCCCN([C@H](C(C)C)C=1N(C=C(N=1)C=1C=C(Cl)C=CC=1)CC=1C=CC=CC=1)C(=O)C1=CC=C(Cl)C(Cl)=C1 IMDUNOBXMILGCH-MUUNZHRXSA-N 0.000 claims 1
- LTWAIKUOFHNFPX-MUUNZHRXSA-N n-(3-aminopropyl)-n-[(1r)-1-[1-benzyl-4-(3-chlorophenyl)imidazol-2-yl]-2-methylpropyl]-3-chlorobenzamide Chemical compound NCCCN([C@H](C(C)C)C=1N(C=C(N=1)C=1C=C(Cl)C=CC=1)CC=1C=CC=CC=1)C(=O)C1=CC=CC(Cl)=C1 LTWAIKUOFHNFPX-MUUNZHRXSA-N 0.000 claims 1
- ZKISHLVBARBRJO-MUUNZHRXSA-N n-(3-aminopropyl)-n-[(1r)-1-[1-benzyl-4-(3-chlorophenyl)imidazol-2-yl]-2-methylpropyl]-4-chlorobenzamide Chemical compound NCCCN([C@H](C(C)C)C=1N(C=C(N=1)C=1C=C(Cl)C=CC=1)CC=1C=CC=CC=1)C(=O)C1=CC=C(Cl)C=C1 ZKISHLVBARBRJO-MUUNZHRXSA-N 0.000 claims 1
- RABALVGUMMYEPA-GDLZYMKVSA-N n-(3-aminopropyl)-n-[(1r)-1-[1-benzyl-4-(3-chlorophenyl)imidazol-2-yl]-2-methylpropyl]-4-methoxybenzamide Chemical compound C1=CC(OC)=CC=C1C(=O)N(CCCN)[C@H](C(C)C)C1=NC(C=2C=C(Cl)C=CC=2)=CN1CC1=CC=CC=C1 RABALVGUMMYEPA-GDLZYMKVSA-N 0.000 claims 1
- RRTFZBNBRAAUMA-AREMUKBSSA-N n-(3-aminopropyl)-n-[(1r)-1-[1-benzyl-4-(3-chlorophenyl)imidazol-2-yl]-2-methylpropyl]-4-methyl-1,2-oxazole-3-carboxamide Chemical compound NCCCN([C@H](C(C)C)C=1N(C=C(N=1)C=1C=C(Cl)C=CC=1)CC=1C=CC=CC=1)C(=O)C1=NOC=C1C RRTFZBNBRAAUMA-AREMUKBSSA-N 0.000 claims 1
- HURAPPWWXYBBCC-GDLZYMKVSA-N n-(3-aminopropyl)-n-[(1r)-1-[1-benzyl-4-(3-chlorophenyl)imidazol-2-yl]-2-methylpropyl]-4-methylbenzamide Chemical compound NCCCN([C@H](C(C)C)C=1N(C=C(N=1)C=1C=C(Cl)C=CC=1)CC=1C=CC=CC=1)C(=O)C1=CC=C(C)C=C1 HURAPPWWXYBBCC-GDLZYMKVSA-N 0.000 claims 1
- IANAWDRZMAPKTG-WJOKGBTCSA-N n-(3-aminopropyl)-n-[(1r)-1-[1-benzyl-4-(3-chlorophenyl)imidazol-2-yl]-2-methylpropyl]-4-tert-butylbenzamide Chemical compound NCCCN([C@H](C(C)C)C=1N(C=C(N=1)C=1C=C(Cl)C=CC=1)CC=1C=CC=CC=1)C(=O)C1=CC=C(C(C)(C)C)C=C1 IANAWDRZMAPKTG-WJOKGBTCSA-N 0.000 claims 1
- PWBZPNMPUFVXMN-AREMUKBSSA-N n-(3-aminopropyl)-n-[(1r)-1-[1-benzyl-4-(3-chlorophenyl)imidazol-2-yl]-2-methylpropyl]-5-methyl-1,2-oxazole-4-carboxamide Chemical compound NCCCN([C@H](C(C)C)C=1N(C=C(N=1)C=1C=C(Cl)C=CC=1)CC=1C=CC=CC=1)C(=O)C=1C=NOC=1C PWBZPNMPUFVXMN-AREMUKBSSA-N 0.000 claims 1
- NKZKFWKEYFIMLW-AREMUKBSSA-N n-(3-aminopropyl)-n-[(1r)-1-[1-benzyl-4-(3-chlorophenyl)imidazol-2-yl]-2-methylpropyl]-5-methyl-1h-pyrazole-3-carboxamide Chemical compound NCCCN([C@H](C(C)C)C=1N(C=C(N=1)C=1C=C(Cl)C=CC=1)CC=1C=CC=CC=1)C(=O)C=1C=C(C)NN=1 NKZKFWKEYFIMLW-AREMUKBSSA-N 0.000 claims 1
- LMNORCQZERUKRY-HHHXNRCGSA-N n-(3-aminopropyl)-n-[(1r)-1-[1-benzyl-4-(3-chlorophenyl)imidazol-2-yl]-2-methylpropyl]-6-chloropyridine-3-carboxamide Chemical compound NCCCN([C@H](C(C)C)C=1N(C=C(N=1)C=1C=C(Cl)C=CC=1)CC=1C=CC=CC=1)C(=O)C1=CC=C(Cl)N=C1 LMNORCQZERUKRY-HHHXNRCGSA-N 0.000 claims 1
- URMKGWFANOZNDQ-AREMUKBSSA-N n-(3-aminopropyl)-n-[(1r)-1-[1-benzyl-4-(3-chlorophenyl)imidazol-2-yl]-2-methylpropyl]furan-3-carboxamide Chemical compound NCCCN([C@H](C(C)C)C=1N(C=C(N=1)C=1C=C(Cl)C=CC=1)CC=1C=CC=CC=1)C(=O)C=1C=COC=1 URMKGWFANOZNDQ-AREMUKBSSA-N 0.000 claims 1
- KCNWYRVOZGEREY-GDLZYMKVSA-N n-(3-aminopropyl)-n-[(1r)-1-[1-benzyl-4-(3-methoxyphenyl)imidazol-2-yl]-2-methylpropyl]-2,4-difluorobenzamide Chemical compound COC1=CC=CC(C=2N=C(N(CC=3C=CC=CC=3)C=2)[C@@H](C(C)C)N(CCCN)C(=O)C=2C(=CC(F)=CC=2)F)=C1 KCNWYRVOZGEREY-GDLZYMKVSA-N 0.000 claims 1
- ILJWSQGHZGSJIL-SSEXGKCCSA-N n-(3-aminopropyl)-n-[(1r)-1-[1-benzyl-4-(3-methoxyphenyl)imidazol-2-yl]-2-methylpropyl]-4-methylbenzamide Chemical compound COC1=CC=CC(C=2N=C(N(CC=3C=CC=CC=3)C=2)[C@@H](C(C)C)N(CCCN)C(=O)C=2C=CC(C)=CC=2)=C1 ILJWSQGHZGSJIL-SSEXGKCCSA-N 0.000 claims 1
- LQBDZJZLTPDCPX-GDLZYMKVSA-N n-(3-aminopropyl)-n-[(1r)-1-[1-benzyl-4-(4-methylphenyl)imidazol-2-yl]-2-methylpropyl]-2,4-difluorobenzamide Chemical compound NCCCN([C@H](C(C)C)C=1N(C=C(N=1)C=1C=CC(C)=CC=1)CC=1C=CC=CC=1)C(=O)C1=CC=C(F)C=C1F LQBDZJZLTPDCPX-GDLZYMKVSA-N 0.000 claims 1
- YCMCSHMZNUIFOU-SSEXGKCCSA-N n-(3-aminopropyl)-n-[(1r)-1-[1-benzyl-4-(4-methylphenyl)imidazol-2-yl]-2-methylpropyl]-4-methylbenzamide Chemical compound NCCCN([C@H](C(C)C)C=1N(C=C(N=1)C=1C=CC(C)=CC=1)CC=1C=CC=CC=1)C(=O)C1=CC=C(C)C=C1 YCMCSHMZNUIFOU-SSEXGKCCSA-N 0.000 claims 1
- FZDNGFHXWNFMAS-MUUNZHRXSA-N n-(3-aminopropyl)-n-[(1r)-1-[1-benzyl-4-[2-(trifluoromethyl)phenyl]imidazol-2-yl]-2-methylpropyl]-2,4-difluorobenzamide Chemical compound NCCCN([C@H](C(C)C)C=1N(C=C(N=1)C=1C(=CC=CC=1)C(F)(F)F)CC=1C=CC=CC=1)C(=O)C1=CC=C(F)C=C1F FZDNGFHXWNFMAS-MUUNZHRXSA-N 0.000 claims 1
- SUHIGEXBHJYEGY-GDLZYMKVSA-N n-(3-aminopropyl)-n-[(1r)-1-[1-benzyl-4-[2-(trifluoromethyl)phenyl]imidazol-2-yl]-2-methylpropyl]-4-methylbenzamide Chemical compound NCCCN([C@H](C(C)C)C=1N(C=C(N=1)C=1C(=CC=CC=1)C(F)(F)F)CC=1C=CC=CC=1)C(=O)C1=CC=C(C)C=C1 SUHIGEXBHJYEGY-GDLZYMKVSA-N 0.000 claims 1
- WWZXEJDITYEDHJ-LJAQVGFWSA-N n-(3-aminopropyl)-n-[(1r)-1-[4-(3-chlorophenyl)-1-[(2,4-difluorophenyl)methyl]imidazol-2-yl]-2,2-dimethylpropyl]-4-methylbenzamide Chemical compound C1=CC(C)=CC=C1C(=O)N(CCCN)[C@H](C(C)(C)C)C1=NC(C=2C=C(Cl)C=CC=2)=CN1CC1=CC=C(F)C=C1F WWZXEJDITYEDHJ-LJAQVGFWSA-N 0.000 claims 1
- LPSXLPDQHCYRHX-SSEXGKCCSA-N n-(3-aminopropyl)-n-[(1r)-1-[4-(3-chlorophenyl)-1-[(3-cyanophenyl)methyl]imidazol-2-yl]-2-methylpropyl]-4-methylbenzamide Chemical compound NCCCN([C@H](C(C)C)C=1N(C=C(N=1)C=1C=C(Cl)C=CC=1)CC=1C=C(C=CC=1)C#N)C(=O)C1=CC=C(C)C=C1 LPSXLPDQHCYRHX-SSEXGKCCSA-N 0.000 claims 1
- HKRNZAXGQTXIGE-SSEXGKCCSA-N n-(3-aminopropyl)-n-[(1r)-1-[4-(3-chlorophenyl)-1-[(3-methylphenyl)methyl]imidazol-2-yl]-2-methylpropyl]-4-methylbenzamide Chemical compound NCCCN([C@H](C(C)C)C=1N(C=C(N=1)C=1C=C(Cl)C=CC=1)CC=1C=C(C)C=CC=1)C(=O)C1=CC=C(C)C=C1 HKRNZAXGQTXIGE-SSEXGKCCSA-N 0.000 claims 1
- GIMOQVJTYLDZBO-NDEPHWFRSA-N n-(3-aminopropyl)-n-[(1r)-2,2-dimethyl-1-[1-[(3-methylphenyl)methyl]-4-phenylimidazol-2-yl]propyl]-1,5-dimethylpyrazole-3-carboxamide Chemical compound CN1C(C)=CC(C(=O)N(CCCN)[C@@H](C=2N(C=C(N=2)C=2C=CC=CC=2)CC=2C=C(C)C=CC=2)C(C)(C)C)=N1 GIMOQVJTYLDZBO-NDEPHWFRSA-N 0.000 claims 1
- DOCODNWABCFGIQ-SANMLTNESA-N n-(3-aminopropyl)-n-[(1r)-2,2-dimethyl-1-[1-[(3-methylphenyl)methyl]-4-phenylimidazol-2-yl]propyl]-2-methoxyacetamide Chemical compound COCC(=O)N(CCCN)[C@H](C(C)(C)C)C1=NC(C=2C=CC=CC=2)=CN1CC1=CC=CC(C)=C1 DOCODNWABCFGIQ-SANMLTNESA-N 0.000 claims 1
- PZVNTPDWNBXVOO-FYBSXPHGSA-N n-(3-aminopropyl)-n-[(1r,2r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2-methylbutyl]-4-methylbenzamide Chemical compound NCCCN([C@H]([C@H](C)CC)C=1N(C=C(N=1)C=1C=CC=CC=1)CC=1C=CC=CC=1)C(=O)C1=CC=C(C)C=C1 PZVNTPDWNBXVOO-FYBSXPHGSA-N 0.000 claims 1
- PZVNTPDWNBXVOO-SETSBSEESA-N n-(3-aminopropyl)-n-[(1r,2s)-1-(1-benzyl-4-phenylimidazol-2-yl)-2-methylbutyl]-4-methylbenzamide Chemical compound NCCCN([C@H]([C@@H](C)CC)C=1N(C=C(N=1)C=1C=CC=CC=1)CC=1C=CC=CC=1)C(=O)C1=CC=C(C)C=C1 PZVNTPDWNBXVOO-SETSBSEESA-N 0.000 claims 1
- XLYSBBZHIVBKHY-JGCGQSQUSA-N n-(3-aminopropyl)-n-[(2r)-2-(1-benzyl-4-phenylimidazol-2-yl)-3-methylbutan-2-yl]-4-methylbenzamide Chemical compound NCCCN([C@](C)(C(C)C)C=1N(C=C(N=1)C=1C=CC=CC=1)CC=1C=CC=CC=1)C(=O)C1=CC=C(C)C=C1 XLYSBBZHIVBKHY-JGCGQSQUSA-N 0.000 claims 1
- QVFVYOOEHCFLJO-JGCGQSQUSA-N n-(3-aminopropyl)-n-[(r)-(1-benzyl-4-phenylimidazol-2-yl)-phenylmethyl]-4-methylbenzamide Chemical compound C1=CC(C)=CC=C1C(=O)N(CCCN)[C@H](C=1C=CC=CC=1)C1=NC(C=2C=CC=CC=2)=CN1CC1=CC=CC=C1 QVFVYOOEHCFLJO-JGCGQSQUSA-N 0.000 claims 1
- GSSMNUMCIXKFQY-UHFFFAOYSA-N n-(3-aminopropyl)-n-[2-[4-(3-fluorophenyl)-1-[(3-fluorophenyl)methyl]imidazol-2-yl]propan-2-yl]-2-methoxyacetamide Chemical compound COCC(=O)N(CCCN)C(C)(C)C1=NC(C=2C=C(F)C=CC=2)=CN1CC1=CC=CC(F)=C1 GSSMNUMCIXKFQY-UHFFFAOYSA-N 0.000 claims 1
- IHQOLCFRWNQNOE-VWLOTQADSA-N n-(azetidin-3-ylmethyl)-n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-2-hydroxyacetamide Chemical compound OCC(=O)N([C@H](C(C)(C)C)C=1N(C=C(N=1)C=1C=CC=CC=1)CC=1C=CC=CC=1)CC1CNC1 IHQOLCFRWNQNOE-VWLOTQADSA-N 0.000 claims 1
- IRHWEQHSRXTVHW-LJAQVGFWSA-N n-(azetidin-3-ylmethyl)-n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-6-methylpyridine-3-carboxamide Chemical compound C1=NC(C)=CC=C1C(=O)N([C@@H](C=1N(C=C(N=1)C=1C=CC=CC=1)CC=1C=CC=CC=1)C(C)(C)C)CC1CNC1 IRHWEQHSRXTVHW-LJAQVGFWSA-N 0.000 claims 1
- KMADIARYKXQKIL-UHSQPCAPSA-N n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-1,5-dimethyl-n-[[(2r)-morpholin-2-yl]methyl]pyrazole-3-carboxamide Chemical compound CN1C(C)=CC(C(=O)N(C[C@@H]2OCCNC2)[C@@H](C=2N(C=C(N=2)C=2C=CC=CC=2)CC=2C=CC=CC=2)C(C)(C)C)=N1 KMADIARYKXQKIL-UHSQPCAPSA-N 0.000 claims 1
- KMADIARYKXQKIL-WNJJXGMVSA-N n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-1,5-dimethyl-n-[[(2s)-morpholin-2-yl]methyl]pyrazole-3-carboxamide Chemical compound CN1C(C)=CC(C(=O)N(C[C@H]2OCCNC2)[C@@H](C=2N(C=C(N=2)C=2C=CC=CC=2)CC=2C=CC=CC=2)C(C)(C)C)=N1 KMADIARYKXQKIL-WNJJXGMVSA-N 0.000 claims 1
- NEUVYGPLDVHIAW-SVEHJYQDSA-N n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-1,5-dimethyl-n-[[(3s)-pyrrolidin-3-yl]methyl]pyrazole-3-carboxamide Chemical compound CN1C(C)=CC(C(=O)N(C[C@@H]2CNCC2)[C@@H](C=2N(C=C(N=2)C=2C=CC=CC=2)CC=2C=CC=CC=2)C(C)(C)C)=N1 NEUVYGPLDVHIAW-SVEHJYQDSA-N 0.000 claims 1
- SQNNKNZZAZOPCG-QFCCLOIZSA-N n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-2-pyrrolidin-3-ylbenzamide Chemical compound N([C@H](C(C)(C)C)C=1N(C=C(N=1)C=1C=CC=CC=1)CC=1C=CC=CC=1)C(=O)C1=CC=CC=C1C1CCNC1 SQNNKNZZAZOPCG-QFCCLOIZSA-N 0.000 claims 1
- BEGJWXTWRFVQCF-MHZLTWQESA-N n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-n-(2,5-dihydro-1h-pyrrol-3-ylmethyl)-2-methoxyacetamide Chemical compound COCC(=O)N([C@@H](C=1N(C=C(N=1)C=1C=CC=CC=1)CC=1C=CC=CC=1)C(C)(C)C)CC1=CCNC1 BEGJWXTWRFVQCF-MHZLTWQESA-N 0.000 claims 1
- OCYNPSRJLYUKBY-QUWDGAPNSA-N n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-n-[(3-hydroxypyrrolidin-3-yl)methyl]-2-methoxyacetamide Chemical compound COCC(=O)N([C@@H](C=1N(C=C(N=1)C=1C=CC=CC=1)CC=1C=CC=CC=1)C(C)(C)C)CC1(O)CCNC1 OCYNPSRJLYUKBY-QUWDGAPNSA-N 0.000 claims 1
- GJFQIJNAXAYSEB-YIOBJHAYSA-N n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-n-[[(2s,3s)-2-(hydroxymethyl)pyrrolidin-3-yl]methyl]-2-methoxyacetamide Chemical compound COCC(=O)N([C@@H](C=1N(C=C(N=1)C=1C=CC=CC=1)CC=1C=CC=CC=1)C(C)(C)C)C[C@@H]1CCN[C@@H]1CO GJFQIJNAXAYSEB-YIOBJHAYSA-N 0.000 claims 1
- PZDFYOARRGQECZ-GMCHKSTQSA-N n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-n-[[(3r)-3-fluoropyrrolidin-3-yl]methyl]-1,5-dimethylpyrazole-3-carboxamide Chemical compound CN1C(C)=CC(C(=O)N(C[C@]2(F)CNCC2)[C@@H](C=2N(C=C(N=2)C=2C=CC=CC=2)CC=2C=CC=CC=2)C(C)(C)C)=N1 PZDFYOARRGQECZ-GMCHKSTQSA-N 0.000 claims 1
- KKVOPPGKSUXKPJ-LITSAYRRSA-N n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-n-[[(3r)-3-fluoropyrrolidin-3-yl]methyl]-2-methoxyacetamide Chemical compound COCC(=O)N([C@@H](C=1N(C=C(N=1)C=1C=CC=CC=1)CC=1C=CC=CC=1)C(C)(C)C)C[C@@]1(F)CCNC1 KKVOPPGKSUXKPJ-LITSAYRRSA-N 0.000 claims 1
- BVWUCUYYLYCZCW-GMCHKSTQSA-N n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-n-[[(3r)-3-hydroxypyrrolidin-3-yl]methyl]-1,5-dimethylpyrazole-3-carboxamide Chemical compound CN1C(C)=CC(C(=O)N(C[C@]2(O)CNCC2)[C@@H](C=2N(C=C(N=2)C=2C=CC=CC=2)CC=2C=CC=CC=2)C(C)(C)C)=N1 BVWUCUYYLYCZCW-GMCHKSTQSA-N 0.000 claims 1
- OCYNPSRJLYUKBY-LITSAYRRSA-N n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-n-[[(3r)-3-hydroxypyrrolidin-3-yl]methyl]-2-methoxyacetamide Chemical compound COCC(=O)N([C@@H](C=1N(C=C(N=1)C=1C=CC=CC=1)CC=1C=CC=CC=1)C(C)(C)C)C[C@@]1(O)CCNC1 OCYNPSRJLYUKBY-LITSAYRRSA-N 0.000 claims 1
- PZDFYOARRGQECZ-IUDBTDONSA-N n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-n-[[(3s)-3-fluoropyrrolidin-3-yl]methyl]-1,5-dimethylpyrazole-3-carboxamide Chemical compound CN1C(C)=CC(C(=O)N(C[C@@]2(F)CNCC2)[C@@H](C=2N(C=C(N=2)C=2C=CC=CC=2)CC=2C=CC=CC=2)C(C)(C)C)=N1 PZDFYOARRGQECZ-IUDBTDONSA-N 0.000 claims 1
- KKVOPPGKSUXKPJ-WNJJXGMVSA-N n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-n-[[(3s)-3-fluoropyrrolidin-3-yl]methyl]-2-methoxyacetamide Chemical compound COCC(=O)N([C@@H](C=1N(C=C(N=1)C=1C=CC=CC=1)CC=1C=CC=CC=1)C(C)(C)C)C[C@]1(F)CCNC1 KKVOPPGKSUXKPJ-WNJJXGMVSA-N 0.000 claims 1
- BVWUCUYYLYCZCW-IUDBTDONSA-N n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-n-[[(3s)-3-hydroxypyrrolidin-3-yl]methyl]-1,5-dimethylpyrazole-3-carboxamide Chemical compound CN1C(C)=CC(C(=O)N(C[C@@]2(O)CNCC2)[C@@H](C=2N(C=C(N=2)C=2C=CC=CC=2)CC=2C=CC=CC=2)C(C)(C)C)=N1 BVWUCUYYLYCZCW-IUDBTDONSA-N 0.000 claims 1
- OCYNPSRJLYUKBY-WNJJXGMVSA-N n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-n-[[(3s)-3-hydroxypyrrolidin-3-yl]methyl]-2-methoxyacetamide Chemical compound COCC(=O)N([C@@H](C=1N(C=C(N=1)C=1C=CC=CC=1)CC=1C=CC=CC=1)C(C)(C)C)C[C@]1(O)CCNC1 OCYNPSRJLYUKBY-WNJJXGMVSA-N 0.000 claims 1
- WKCJGUICTMYNJL-NDEPHWFRSA-N n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-n-butyl-1,5-dimethylpyrazole-3-carboxamide Chemical compound C1([C@H](N(CCCC)C(=O)C2=NN(C)C(C)=C2)C(C)(C)C)=NC(C=2C=CC=CC=2)=CN1CC1=CC=CC=C1 WKCJGUICTMYNJL-NDEPHWFRSA-N 0.000 claims 1
- DPUSEAMVXZJJMB-LJAQVGFWSA-N n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-n-butylbenzamide Chemical compound C1([C@H](N(CCCC)C(=O)C=2C=CC=CC=2)C(C)(C)C)=NC(C=2C=CC=CC=2)=CN1CC1=CC=CC=C1 DPUSEAMVXZJJMB-LJAQVGFWSA-N 0.000 claims 1
- YMTJBMCVDPJQRS-NDEPHWFRSA-N n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-n-propylbenzamide Chemical compound C1([C@H](N(CCC)C(=O)C=2C=CC=CC=2)C(C)(C)C)=NC(C=2C=CC=CC=2)=CN1CC1=CC=CC=C1 YMTJBMCVDPJQRS-NDEPHWFRSA-N 0.000 claims 1
- MDABRPVOPFHXDG-NPRFROTHSA-N n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2-methylpropyl]-1,5-dimethyl-n-(piperidin-3-ylmethyl)pyrazole-3-carboxamide Chemical compound C1=C(C)N(C)N=C1C(=O)N([C@H](C(C)C)C=1N(C=C(N=1)C=1C=CC=CC=1)CC=1C=CC=CC=1)CC1CCCNC1 MDABRPVOPFHXDG-NPRFROTHSA-N 0.000 claims 1
- HHXBNQRDQWPGDC-SSEXGKCCSA-N n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2-methylpropyl]-2,4-difluoro-n-piperidin-4-ylbenzamide Chemical compound C=1C=C(F)C=C(F)C=1C(=O)N([C@H](C(C)C)C=1N(C=C(N=1)C=1C=CC=CC=1)CC=1C=CC=CC=1)C1CCNCC1 HHXBNQRDQWPGDC-SSEXGKCCSA-N 0.000 claims 1
- XCPXWPYCJABOSJ-WJOKGBTCSA-N n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2-methylpropyl]-4-methyl-n-piperidin-4-ylbenzamide Chemical compound C=1C=C(C)C=CC=1C(=O)N([C@H](C(C)C)C=1N(C=C(N=1)C=1C=CC=CC=1)CC=1C=CC=CC=1)C1CCNCC1 XCPXWPYCJABOSJ-WJOKGBTCSA-N 0.000 claims 1
- GYDLOJZKHHRCKY-AREMUKBSSA-N n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2-methylpropyl]-4-methylbenzamide Chemical compound N([C@H](C(C)C)C=1N(C=C(N=1)C=1C=CC=CC=1)CC=1C=CC=CC=1)C(=O)C1=CC=C(C)C=C1 GYDLOJZKHHRCKY-AREMUKBSSA-N 0.000 claims 1
- PZRYDZBICCPPRB-SSEXGKCCSA-N n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2-methylpropyl]-n-piperidin-4-ylbenzamide Chemical compound C=1C=CC=CC=1C(=O)N([C@H](C(C)C)C=1N(C=C(N=1)C=1C=CC=CC=1)CC=1C=CC=CC=1)C1CCNCC1 PZRYDZBICCPPRB-SSEXGKCCSA-N 0.000 claims 1
- FWMJZTNHPWPXAR-VWLOTQADSA-N n-[(1r)-1-[1-benzyl-4-(2,5-difluorophenyl)imidazol-2-yl]-2,2-dimethylpropyl]-2-methoxy-n-(2h-triazol-4-ylmethyl)acetamide Chemical compound COCC(=O)N([C@@H](C=1N(C=C(N=1)C=1C(=CC=C(F)C=1)F)CC=1C=CC=CC=1)C(C)(C)C)CC1=CNN=N1 FWMJZTNHPWPXAR-VWLOTQADSA-N 0.000 claims 1
- VGVBOZCDOCQDMW-HOINCLMKSA-N n-[(1r)-1-[1-benzyl-4-(3-chlorophenyl)imidazol-2-yl]-2-methylpropyl]-2-pyrrolidin-3-ylbenzamide Chemical compound N([C@H](C(C)C)C=1N(C=C(N=1)C=1C=C(Cl)C=CC=1)CC=1C=CC=CC=1)C(=O)C1=CC=CC=C1C1CCNC1 VGVBOZCDOCQDMW-HOINCLMKSA-N 0.000 claims 1
- DQUAMJZCQWTDJE-SSEXGKCCSA-N n-[(1r)-1-[1-benzyl-4-(3-chlorophenyl)imidazol-2-yl]-2-methylpropyl]-n-piperidin-4-ylbenzamide Chemical compound C=1C=CC=CC=1C(=O)N([C@H](C(C)C)C=1N(C=C(N=1)C=1C=C(Cl)C=CC=1)CC=1C=CC=CC=1)C1CCNCC1 DQUAMJZCQWTDJE-SSEXGKCCSA-N 0.000 claims 1
- KKNJIFHJFHNNQP-PBBNMVCDSA-N n-[(1r)-1-[4-(3-chlorophenyl)-1-[(3,5-difluorophenyl)methyl]imidazol-2-yl]-2,2-dimethylpropyl]-1,5-dimethyl-n-[[(3r)-pyrrolidin-3-yl]methyl]pyrazole-3-carboxamide Chemical compound CN1C(C)=CC(C(=O)N(C[C@H]2CNCC2)[C@@H](C=2N(C=C(N=2)C=2C=C(Cl)C=CC=2)CC=2C=C(F)C=C(F)C=2)C(C)(C)C)=N1 KKNJIFHJFHNNQP-PBBNMVCDSA-N 0.000 claims 1
- KKNJIFHJFHNNQP-LGGPFLRQSA-N n-[(1r)-1-[4-(3-chlorophenyl)-1-[(3,5-difluorophenyl)methyl]imidazol-2-yl]-2,2-dimethylpropyl]-1,5-dimethyl-n-[[(3s)-pyrrolidin-3-yl]methyl]pyrazole-3-carboxamide Chemical compound CN1C(C)=CC(C(=O)N(C[C@@H]2CNCC2)[C@@H](C=2N(C=C(N=2)C=2C=C(Cl)C=CC=2)CC=2C=C(F)C=C(F)C=2)C(C)(C)C)=N1 KKNJIFHJFHNNQP-LGGPFLRQSA-N 0.000 claims 1
- ZRMUYTFXDSKIAH-WSXWNZDHSA-N n-[(1r)-2,2-dimethyl-1-[1-[(3-methylphenyl)methyl]-4-phenylimidazol-2-yl]propyl]-1,5-dimethyl-n-(pyrrolidin-3-ylmethyl)pyrazole-3-carboxamide Chemical compound CN1C(C)=CC(C(=O)N(CC2CNCC2)[C@@H](C=2N(C=C(N=2)C=2C=CC=CC=2)CC=2C=C(C)C=CC=2)C(C)(C)C)=N1 ZRMUYTFXDSKIAH-WSXWNZDHSA-N 0.000 claims 1
- VZUCQWGOEQGZLK-SQHAQQRYSA-N n-[(2r)-3-amino-2-fluoropropyl]-n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-1,5-dimethylpyrazole-3-carboxamide Chemical compound CN1C(C)=CC(C(=O)N(C[C@H](F)CN)[C@@H](C=2N(C=C(N=2)C=2C=CC=CC=2)CC=2C=CC=CC=2)C(C)(C)C)=N1 VZUCQWGOEQGZLK-SQHAQQRYSA-N 0.000 claims 1
- WCZBOQVBIANBTC-BVAGGSTKSA-N n-[(2r)-3-amino-2-fluoropropyl]-n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-2-ethoxyacetamide Chemical compound CCOCC(=O)N(C[C@H](F)CN)[C@H](C(C)(C)C)C1=NC(C=2C=CC=CC=2)=CN1CC1=CC=CC=C1 WCZBOQVBIANBTC-BVAGGSTKSA-N 0.000 claims 1
- BBIOTVZBHYJSCZ-QPPBQGQZSA-N n-[(2r)-3-amino-2-fluoropropyl]-n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-2-hydroxyacetamide Chemical compound NC[C@@H](F)CN(C(=O)CO)[C@H](C(C)(C)C)C1=NC(C=2C=CC=CC=2)=CN1CC1=CC=CC=C1 BBIOTVZBHYJSCZ-QPPBQGQZSA-N 0.000 claims 1
- DYUATSGEGUZWBI-RDGATRHJSA-N n-[(2r)-3-amino-2-fluoropropyl]-n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound COCC(=O)N(C[C@H](F)CN)[C@H](C(C)(C)C)C1=NC(C=2C=CC=CC=2)=CN1CC1=CC=CC=C1 DYUATSGEGUZWBI-RDGATRHJSA-N 0.000 claims 1
- SNMGFPUXBLEBRW-YKSBVNFPSA-N n-[(2r)-3-amino-2-fluoropropyl]-n-[(1r)-1-(1-benzyl-4-pyrazin-2-ylimidazol-2-yl)-2,2-dimethylpropyl]-2-ethoxyacetamide Chemical compound CCOCC(=O)N(C[C@H](F)CN)[C@H](C(C)(C)C)C1=NC(C=2N=CC=NC=2)=CN1CC1=CC=CC=C1 SNMGFPUXBLEBRW-YKSBVNFPSA-N 0.000 claims 1
- POXFRGZDQSLIGM-XXBNENTESA-N n-[(2r)-3-amino-2-fluoropropyl]-n-[(1r)-1-(1-benzyl-4-pyrazin-2-ylimidazol-2-yl)-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound COCC(=O)N(C[C@H](F)CN)[C@H](C(C)(C)C)C1=NC(C=2N=CC=NC=2)=CN1CC1=CC=CC=C1 POXFRGZDQSLIGM-XXBNENTESA-N 0.000 claims 1
- PNXSIQWXEUJDQO-QPPBQGQZSA-N n-[(2r)-3-amino-2-fluoropropyl]-n-[(1r)-1-(1-benzyl-5-chloro-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound COCC(=O)N(C[C@H](F)CN)[C@H](C(C)(C)C)C1=NC(C=2C=CC=CC=2)=C(Cl)N1CC1=CC=CC=C1 PNXSIQWXEUJDQO-QPPBQGQZSA-N 0.000 claims 1
- GZQMSCKWTQLWGG-BWKNWUBXSA-N n-[(2r)-3-amino-2-fluoropropyl]-n-[(1r)-1-[1-[(2-fluorophenyl)methyl]-4-phenylimidazol-2-yl]-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound COCC(=O)N(C[C@H](F)CN)[C@H](C(C)(C)C)C1=NC(C=2C=CC=CC=2)=CN1CC1=CC=CC=C1F GZQMSCKWTQLWGG-BWKNWUBXSA-N 0.000 claims 1
- YWJBXMUIVDAJMZ-RDGATRHJSA-N n-[(2r)-3-amino-2-fluoropropyl]-n-[(1r)-1-[1-[(3-chlorophenyl)methyl]-4-phenylimidazol-2-yl]-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound COCC(=O)N(C[C@H](F)CN)[C@H](C(C)(C)C)C1=NC(C=2C=CC=CC=2)=CN1CC1=CC=CC(Cl)=C1 YWJBXMUIVDAJMZ-RDGATRHJSA-N 0.000 claims 1
- VWJWCKFKFJLFEM-BVAGGSTKSA-N n-[(2r)-3-amino-2-fluoropropyl]-n-[(1r)-1-[1-[(3-cyanophenyl)methyl]-4-phenylimidazol-2-yl]-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound COCC(=O)N(C[C@H](F)CN)[C@H](C(C)(C)C)C1=NC(C=2C=CC=CC=2)=CN1CC1=CC=CC(C#N)=C1 VWJWCKFKFJLFEM-BVAGGSTKSA-N 0.000 claims 1
- TWZTXGFYVHCZNY-RDGATRHJSA-N n-[(2r)-3-amino-2-fluoropropyl]-n-[(1r)-1-[1-[(3-fluorophenyl)methyl]-4-phenylimidazol-2-yl]-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound COCC(=O)N(C[C@H](F)CN)[C@H](C(C)(C)C)C1=NC(C=2C=CC=CC=2)=CN1CC1=CC=CC(F)=C1 TWZTXGFYVHCZNY-RDGATRHJSA-N 0.000 claims 1
- FDYNAZBNYZKTKY-RLWLMLJZSA-N n-[(2r)-3-amino-2-fluoropropyl]-n-[(1r)-1-[1-benzyl-4-(2-methoxyphenyl)imidazol-2-yl]-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound COCC(=O)N(C[C@H](F)CN)[C@H](C(C)(C)C)C1=NC(C=2C(=CC=CC=2)OC)=CN1CC1=CC=CC=C1 FDYNAZBNYZKTKY-RLWLMLJZSA-N 0.000 claims 1
- IFNUQKWPGWHMKZ-RDGATRHJSA-N n-[(2r)-3-amino-2-fluoropropyl]-n-[(1r)-1-[1-benzyl-4-(3-bromophenyl)imidazol-2-yl]-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound COCC(=O)N(C[C@H](F)CN)[C@H](C(C)(C)C)C1=NC(C=2C=C(Br)C=CC=2)=CN1CC1=CC=CC=C1 IFNUQKWPGWHMKZ-RDGATRHJSA-N 0.000 claims 1
- BVTZFVPYGALBDF-RDGATRHJSA-N n-[(2r)-3-amino-2-fluoropropyl]-n-[(1r)-1-[1-benzyl-4-(3-fluorophenyl)imidazol-2-yl]-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound COCC(=O)N(C[C@H](F)CN)[C@H](C(C)(C)C)C1=NC(C=2C=C(F)C=CC=2)=CN1CC1=CC=CC=C1 BVTZFVPYGALBDF-RDGATRHJSA-N 0.000 claims 1
- JWEVFWUVQPDICT-KCWPFWIISA-N n-[(2r)-3-amino-2-fluoropropyl]-n-[(1r)-1-[1-benzyl-4-(3-methoxyphenyl)imidazol-2-yl]-2,2-dimethylpropyl]-2-ethoxyacetamide Chemical compound CCOCC(=O)N(C[C@H](F)CN)[C@H](C(C)(C)C)C1=NC(C=2C=C(OC)C=CC=2)=CN1CC1=CC=CC=C1 JWEVFWUVQPDICT-KCWPFWIISA-N 0.000 claims 1
- PBGWTNNXQJVIQT-GJZUVCINSA-N n-[(2r)-3-amino-2-fluoropropyl]-n-[(1r)-1-[1-benzyl-4-(3-methoxyphenyl)imidazol-2-yl]-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound COCC(=O)N(C[C@H](F)CN)[C@H](C(C)(C)C)C1=NC(C=2C=C(OC)C=CC=2)=CN1CC1=CC=CC=C1 PBGWTNNXQJVIQT-GJZUVCINSA-N 0.000 claims 1
- LHFJGZSOGAVQEW-BVAGGSTKSA-N n-[(2r)-3-amino-2-fluoropropyl]-n-[(1r)-1-[1-benzyl-4-(4-cyanophenyl)imidazol-2-yl]-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound COCC(=O)N(C[C@H](F)CN)[C@H](C(C)(C)C)C1=NC(C=2C=CC(=CC=2)C#N)=CN1CC1=CC=CC=C1 LHFJGZSOGAVQEW-BVAGGSTKSA-N 0.000 claims 1
- UCFZXUJNGMQORT-GJZUVCINSA-N n-[(2r)-3-amino-2-fluoropropyl]-n-[(1r)-1-[1-benzyl-4-(4-methoxyphenyl)imidazol-2-yl]-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound COCC(=O)N(C[C@H](F)CN)[C@H](C(C)(C)C)C1=NC(C=2C=CC(OC)=CC=2)=CN1CC1=CC=CC=C1 UCFZXUJNGMQORT-GJZUVCINSA-N 0.000 claims 1
- QQVINCSIWDBERZ-BVAGGSTKSA-N n-[(2r)-3-amino-2-fluoropropyl]-n-[(1r)-1-[1-benzyl-4-(4-methylphenyl)imidazol-2-yl]-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound COCC(=O)N(C[C@H](F)CN)[C@H](C(C)(C)C)C1=NC(C=2C=CC(C)=CC=2)=CN1CC1=CC=CC=C1 QQVINCSIWDBERZ-BVAGGSTKSA-N 0.000 claims 1
- DHMSMLGGNRJRFJ-RDGATRHJSA-N n-[(2r)-3-amino-2-fluoropropyl]-n-[(1r)-1-[1-benzyl-4-[3-(trifluoromethyl)phenyl]imidazol-2-yl]-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound COCC(=O)N(C[C@H](F)CN)[C@H](C(C)(C)C)C1=NC(C=2C=C(C=CC=2)C(F)(F)F)=CN1CC1=CC=CC=C1 DHMSMLGGNRJRFJ-RDGATRHJSA-N 0.000 claims 1
- OKGBBYGWPJWRBU-QPPBQGQZSA-N n-[(2r)-3-amino-2-fluoropropyl]-n-[(1r)-2,2-dimethyl-1-[1-(oxan-4-ylmethyl)-4-phenylimidazol-2-yl]propyl]-2-methoxyacetamide Chemical compound COCC(=O)N(C[C@H](F)CN)[C@H](C(C)(C)C)C1=NC(C=2C=CC=CC=2)=CN1CC1CCOCC1 OKGBBYGWPJWRBU-QPPBQGQZSA-N 0.000 claims 1
- VZUCQWGOEQGZLK-IGKIAQTJSA-N n-[(2s)-3-amino-2-fluoropropyl]-n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-1,5-dimethylpyrazole-3-carboxamide Chemical compound CN1C(C)=CC(C(=O)N(C[C@@H](F)CN)[C@@H](C=2N(C=C(N=2)C=2C=CC=CC=2)CC=2C=CC=CC=2)C(C)(C)C)=N1 VZUCQWGOEQGZLK-IGKIAQTJSA-N 0.000 claims 1
- DYUATSGEGUZWBI-DHLKQENFSA-N n-[(2s)-3-amino-2-fluoropropyl]-n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound COCC(=O)N(C[C@@H](F)CN)[C@H](C(C)(C)C)C1=NC(C=2C=CC=CC=2)=CN1CC1=CC=CC=C1 DYUATSGEGUZWBI-DHLKQENFSA-N 0.000 claims 1
- AHCAXAUQDICGNN-HKUYNNGSSA-N n-[(2s)-3-amino-2-fluoropropyl]-n-[(1r)-1-(1-benzylimidazol-2-yl)-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound COCC(=O)N(C[C@@H](F)CN)[C@H](C(C)(C)C)C1=NC=CN1CC1=CC=CC=C1 AHCAXAUQDICGNN-HKUYNNGSSA-N 0.000 claims 1
- RIBXLYCCAYCDJI-RXVVDRJESA-N n-[(2s)-3-amino-2-fluoropropyl]-n-[(1r)-1-[1-benzyl-4-(1,3-thiazol-2-yl)imidazol-2-yl]-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound COCC(=O)N(C[C@@H](F)CN)[C@H](C(C)(C)C)C1=NC(C=2SC=CN=2)=CN1CC1=CC=CC=C1 RIBXLYCCAYCDJI-RXVVDRJESA-N 0.000 claims 1
- IYJVDGTZPONDRW-CVDCTZTESA-N n-[(2s)-3-amino-2-fluoropropyl]-n-[(1r)-2,2-dimethyl-1-[1-[(5-methyl-1,2-oxazol-3-yl)methyl]-4-phenylimidazol-2-yl]propyl]-2-methoxyacetamide Chemical compound COCC(=O)N(C[C@@H](F)CN)[C@H](C(C)(C)C)C1=NC(C=2C=CC=CC=2)=CN1CC=1C=C(C)ON=1 IYJVDGTZPONDRW-CVDCTZTESA-N 0.000 claims 1
- BWKIFSGVUJASBM-MBSDFSHPSA-N n-[(2s)-3-amino-2-fluoropropyl]-n-[(1r)-2,2-dimethyl-1-[4-phenyl-1-[[5-(trifluoromethyl)furan-2-yl]methyl]imidazol-2-yl]propyl]-2-methoxyacetamide Chemical compound COCC(=O)N(C[C@@H](F)CN)[C@H](C(C)(C)C)C1=NC(C=2C=CC=CC=2)=CN1CC1=CC=C(C(F)(F)F)O1 BWKIFSGVUJASBM-MBSDFSHPSA-N 0.000 claims 1
- SQMHRJMKOKJYSN-IGKIAQTJSA-N n-[(2s)-3-amino-2-hydroxypropyl]-n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-1,5-dimethylpyrazole-3-carboxamide Chemical compound CN1C(C)=CC(C(=O)N(C[C@@H](O)CN)[C@@H](C=2N(C=C(N=2)C=2C=CC=CC=2)CC=2C=CC=CC=2)C(C)(C)C)=N1 SQMHRJMKOKJYSN-IGKIAQTJSA-N 0.000 claims 1
- VRRBROKENKCDMZ-URXFXBBRSA-N n-[(2s)-3-amino-2-hydroxypropyl]-n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-2-hydroxyacetamide Chemical compound NC[C@H](O)CN(C(=O)CO)[C@H](C(C)(C)C)C1=NC(C=2C=CC=CC=2)=CN1CC1=CC=CC=C1 VRRBROKENKCDMZ-URXFXBBRSA-N 0.000 claims 1
- NRKOYMYHGKGMHQ-DHLKQENFSA-N n-[(2s)-3-amino-2-hydroxypropyl]-n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound COCC(=O)N(C[C@@H](O)CN)[C@H](C(C)(C)C)C1=NC(C=2C=CC=CC=2)=CN1CC1=CC=CC=C1 NRKOYMYHGKGMHQ-DHLKQENFSA-N 0.000 claims 1
- XAQHNLSFRDUHOG-ZEVJAHDQSA-N n-[(2s,3r)-3-amino-2-fluoro-4-hydroxybutyl]-n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound OC[C@@H](N)[C@@H](F)CN(C(=O)COC)[C@H](C(C)(C)C)C1=NC(C=2C=CC=CC=2)=CN1CC1=CC=CC=C1 XAQHNLSFRDUHOG-ZEVJAHDQSA-N 0.000 claims 1
- OKESKHOQGQXOKK-BVAGGSTKSA-N n-[(3r)-3-amino-4-fluorobutyl]-n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound FC[C@H](N)CCN(C(=O)COC)[C@H](C(C)(C)C)C1=NC(C=2C=CC=CC=2)=CN1CC1=CC=CC=C1 OKESKHOQGQXOKK-BVAGGSTKSA-N 0.000 claims 1
- GOPFSRHTPZOKHP-RLWLMLJZSA-N n-[(3r)-3-amino-4-fluorobutyl]-n-[(1r)-1-[1-benzyl-4-(2,5-difluorophenyl)imidazol-2-yl]-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound FC[C@H](N)CCN(C(=O)COC)[C@H](C(C)(C)C)C1=NC(C=2C(=CC=C(F)C=2)F)=CN1CC1=CC=CC=C1 GOPFSRHTPZOKHP-RLWLMLJZSA-N 0.000 claims 1
- QYSUSIMQIRYFJE-BVAGGSTKSA-N n-[(3r)-3-amino-4-fluorobutyl]-n-[(1r)-1-[1-benzyl-4-(3-fluorophenyl)imidazol-2-yl]-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound FC[C@H](N)CCN(C(=O)COC)[C@H](C(C)(C)C)C1=NC(C=2C=C(F)C=CC=2)=CN1CC1=CC=CC=C1 QYSUSIMQIRYFJE-BVAGGSTKSA-N 0.000 claims 1
- XEATZEUDKZHOEZ-BVAGGSTKSA-N n-[(3r)-3-amino-4-fluorobutyl]-n-[(1r)-1-[4-(3-fluorophenyl)-1-[(3-fluorophenyl)methyl]imidazol-2-yl]-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound FC[C@H](N)CCN(C(=O)COC)[C@H](C(C)(C)C)C1=NC(C=2C=C(F)C=CC=2)=CN1CC1=CC=CC(F)=C1 XEATZEUDKZHOEZ-BVAGGSTKSA-N 0.000 claims 1
- HTIOQAFZTXDABM-GJZUVCINSA-N n-[(3r)-3-amino-4-fluorobutyl]-n-[(1r)-1-[4-(3-fluorophenyl)-1-[(3-hydroxyphenyl)methyl]imidazol-2-yl]-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound FC[C@H](N)CCN(C(=O)COC)[C@H](C(C)(C)C)C1=NC(C=2C=C(F)C=CC=2)=CN1CC1=CC=CC(O)=C1 HTIOQAFZTXDABM-GJZUVCINSA-N 0.000 claims 1
- AAFVIVHMKRCWCE-YKSBVNFPSA-N n-[(3r)-3-amino-4-fluorobutyl]-n-[(1r)-2,2-dimethyl-1-[1-[(5-methyl-1,2-oxazol-3-yl)methyl]-4-phenylimidazol-2-yl]propyl]-2-methoxyacetamide Chemical compound FC[C@H](N)CCN(C(=O)COC)[C@H](C(C)(C)C)C1=NC(C=2C=CC=CC=2)=CN1CC=1C=C(C)ON=1 AAFVIVHMKRCWCE-YKSBVNFPSA-N 0.000 claims 1
- AJWQLUZHVTUSDN-BVAGGSTKSA-N n-[(3r)-3-amino-4-hydroxybutyl]-n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound OC[C@H](N)CCN(C(=O)COC)[C@H](C(C)(C)C)C1=NC(C=2C=CC=CC=2)=CN1CC1=CC=CC=C1 AJWQLUZHVTUSDN-BVAGGSTKSA-N 0.000 claims 1
- UEWJIRMMZRGAEE-BCHFMIIMSA-N n-[(3r)-3-aminobutyl]-n-[(1r)-1-[1-benzyl-4-(2,5-difluorophenyl)imidazol-2-yl]-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound COCC(=O)N(CC[C@@H](C)N)[C@H](C(C)(C)C)C1=NC(C=2C(=CC=C(F)C=2)F)=CN1CC1=CC=CC=C1 UEWJIRMMZRGAEE-BCHFMIIMSA-N 0.000 claims 1
- SJSLQVAPQCYQHF-BCHFMIIMSA-N n-[(3r)-3-aminobutyl]-n-[(1r)-1-[4-(3-fluorophenyl)-1-[(3-fluorophenyl)methyl]imidazol-2-yl]-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound COCC(=O)N(CC[C@@H](C)N)[C@H](C(C)(C)C)C1=NC(C=2C=C(F)C=CC=2)=CN1CC1=CC=CC(F)=C1 SJSLQVAPQCYQHF-BCHFMIIMSA-N 0.000 claims 1
- KHQKJSUOOKSGOB-NVQXNPDNSA-N n-[(3s)-3-amino-4-fluorobutyl]-n-[(1r)-1-[1-[(2,5-difluorophenyl)methyl]-4-phenylimidazol-2-yl]-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound FC[C@@H](N)CCN(C(=O)COC)[C@H](C(C)(C)C)C1=NC(C=2C=CC=CC=2)=CN1CC1=CC(F)=CC=C1F KHQKJSUOOKSGOB-NVQXNPDNSA-N 0.000 claims 1
- QXIKQDYUFDINPI-CPJSRVTESA-N n-[(3s)-3-amino-4-fluorobutyl]-n-[(1r)-1-[1-[(6-aminopyridin-2-yl)methyl]-4-(3-fluorophenyl)imidazol-2-yl]-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound FC[C@@H](N)CCN(C(=O)COC)[C@H](C(C)(C)C)C1=NC(C=2C=C(F)C=CC=2)=CN1CC1=CC=CC(N)=N1 QXIKQDYUFDINPI-CPJSRVTESA-N 0.000 claims 1
- XIXUMQPZFFQIHN-UGKGYDQZSA-N n-[(3s)-3-amino-4-fluorobutyl]-n-[(1r)-1-[1-benzyl-4-(1,3-thiazol-2-yl)imidazol-2-yl]-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound FC[C@@H](N)CCN(C(=O)COC)[C@H](C(C)(C)C)C1=NC(C=2SC=CN=2)=CN1CC1=CC=CC=C1 XIXUMQPZFFQIHN-UGKGYDQZSA-N 0.000 claims 1
- GOPFSRHTPZOKHP-LVXARBLLSA-N n-[(3s)-3-amino-4-fluorobutyl]-n-[(1r)-1-[1-benzyl-4-(2,5-difluorophenyl)imidazol-2-yl]-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound FC[C@@H](N)CCN(C(=O)COC)[C@H](C(C)(C)C)C1=NC(C=2C(=CC=C(F)C=2)F)=CN1CC1=CC=CC=C1 GOPFSRHTPZOKHP-LVXARBLLSA-N 0.000 claims 1
- AQNFWEVZJZQGMZ-JYFHCDHNSA-N n-[(3s)-3-amino-4-fluorobutyl]-n-[(1r)-1-[1-benzyl-4-(3-chlorophenyl)imidazol-2-yl]-2-methylpropyl]-2-methoxyacetamide Chemical compound FC[C@@H](N)CCN(C(=O)COC)[C@H](C(C)C)C1=NC(C=2C=C(Cl)C=CC=2)=CN1CC1=CC=CC=C1 AQNFWEVZJZQGMZ-JYFHCDHNSA-N 0.000 claims 1
- QYSUSIMQIRYFJE-OZXSUGGESA-N n-[(3s)-3-amino-4-fluorobutyl]-n-[(1r)-1-[1-benzyl-4-(3-fluorophenyl)imidazol-2-yl]-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound FC[C@@H](N)CCN(C(=O)COC)[C@H](C(C)(C)C)C1=NC(C=2C=C(F)C=CC=2)=CN1CC1=CC=CC=C1 QYSUSIMQIRYFJE-OZXSUGGESA-N 0.000 claims 1
- HELUOOCXLLBAOD-OZXSUGGESA-N n-[(3s)-3-amino-4-fluorobutyl]-n-[(1r)-1-[1-benzyl-5-(3-fluorophenyl)imidazol-2-yl]-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound C=1C=CC=CC=1CN1C([C@H](N(CC[C@H](N)CF)C(=O)COC)C(C)(C)C)=NC=C1C1=CC=CC(F)=C1 HELUOOCXLLBAOD-OZXSUGGESA-N 0.000 claims 1
- JOYLJUMXXGGDMB-JYFHCDHNSA-N n-[(3s)-3-amino-4-fluorobutyl]-n-[(1r)-1-[4-(3-chlorophenyl)-1-[(3-fluorophenyl)methyl]imidazol-2-yl]-2-methylpropyl]-2-methoxyacetamide Chemical compound FC[C@@H](N)CCN(C(=O)COC)[C@H](C(C)C)C1=NC(C=2C=C(Cl)C=CC=2)=CN1CC1=CC=CC(F)=C1 JOYLJUMXXGGDMB-JYFHCDHNSA-N 0.000 claims 1
- XEATZEUDKZHOEZ-OZXSUGGESA-N n-[(3s)-3-amino-4-fluorobutyl]-n-[(1r)-1-[4-(3-fluorophenyl)-1-[(3-fluorophenyl)methyl]imidazol-2-yl]-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound FC[C@@H](N)CCN(C(=O)COC)[C@H](C(C)(C)C)C1=NC(C=2C=C(F)C=CC=2)=CN1CC1=CC=CC(F)=C1 XEATZEUDKZHOEZ-OZXSUGGESA-N 0.000 claims 1
- HTIOQAFZTXDABM-NVQXNPDNSA-N n-[(3s)-3-amino-4-fluorobutyl]-n-[(1r)-1-[4-(3-fluorophenyl)-1-[(3-hydroxyphenyl)methyl]imidazol-2-yl]-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound FC[C@@H](N)CCN(C(=O)COC)[C@H](C(C)(C)C)C1=NC(C=2C=C(F)C=CC=2)=CN1CC1=CC=CC(O)=C1 HTIOQAFZTXDABM-NVQXNPDNSA-N 0.000 claims 1
- AAFVIVHMKRCWCE-RDPSFJRHSA-N n-[(3s)-3-amino-4-fluorobutyl]-n-[(1r)-2,2-dimethyl-1-[1-[(5-methyl-1,2-oxazol-3-yl)methyl]-4-phenylimidazol-2-yl]propyl]-2-methoxyacetamide Chemical compound FC[C@@H](N)CCN(C(=O)COC)[C@H](C(C)(C)C)C1=NC(C=2C=CC=CC=2)=CN1CC=1C=C(C)ON=1 AAFVIVHMKRCWCE-RDPSFJRHSA-N 0.000 claims 1
- FIDUXLJKMQXNRA-LSYYVWMOSA-N n-[(3s)-3-amino-4-hydroxybutyl]-n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-1,5-dimethylpyrazole-3-carboxamide Chemical compound CN1C(C)=CC(C(=O)N(CC[C@H](N)CO)[C@@H](C=2N(C=C(N=2)C=2C=CC=CC=2)CC=2C=CC=CC=2)C(C)(C)C)=N1 FIDUXLJKMQXNRA-LSYYVWMOSA-N 0.000 claims 1
- AJWQLUZHVTUSDN-OZXSUGGESA-N n-[(3s)-3-amino-4-hydroxybutyl]-n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound OC[C@@H](N)CCN(C(=O)COC)[C@H](C(C)(C)C)C1=NC(C=2C=CC=CC=2)=CN1CC1=CC=CC=C1 AJWQLUZHVTUSDN-OZXSUGGESA-N 0.000 claims 1
- OQANZRKOWRKXIM-OZXSUGGESA-N n-[(3s)-3-amino-4-hydroxybutyl]-n-[(1r)-1-[1-benzyl-4-(3-fluorophenyl)imidazol-2-yl]-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound OC[C@@H](N)CCN(C(=O)COC)[C@H](C(C)(C)C)C1=NC(C=2C=C(F)C=CC=2)=CN1CC1=CC=CC=C1 OQANZRKOWRKXIM-OZXSUGGESA-N 0.000 claims 1
- JBDKUKGMYNZRJN-OZXSUGGESA-N n-[(3s)-3-amino-4-hydroxybutyl]-n-[(1r)-1-[4-(3-fluorophenyl)-1-[(3-fluorophenyl)methyl]imidazol-2-yl]-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound OC[C@@H](N)CCN(C(=O)COC)[C@H](C(C)(C)C)C1=NC(C=2C=C(F)C=CC=2)=CN1CC1=CC=CC(F)=C1 JBDKUKGMYNZRJN-OZXSUGGESA-N 0.000 claims 1
- VOGRGMOUVOHNQQ-IGKIAQTJSA-N n-[(3s)-3-amino-4-methoxybutyl]-n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound COC[C@@H](N)CCN(C(=O)COC)[C@H](C(C)(C)C)C1=NC(C=2C=CC=CC=2)=CN1CC1=CC=CC=C1 VOGRGMOUVOHNQQ-IGKIAQTJSA-N 0.000 claims 1
- UDTMCYMUEYEYPV-CUNXSJBXSA-N n-[(3s)-3-amino-4-methoxybutyl]-n-[(1r)-1-[1-benzyl-4-(2,5-difluorophenyl)imidazol-2-yl]-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound COC[C@@H](N)CCN(C(=O)COC)[C@H](C(C)(C)C)C1=NC(C=2C(=CC=C(F)C=2)F)=CN1CC1=CC=CC=C1 UDTMCYMUEYEYPV-CUNXSJBXSA-N 0.000 claims 1
- YCKIVXRVVNMXIK-IGKIAQTJSA-N n-[(3s)-3-amino-4-methoxybutyl]-n-[(1r)-1-[1-benzyl-4-(3-fluorophenyl)imidazol-2-yl]-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound COC[C@@H](N)CCN(C(=O)COC)[C@H](C(C)(C)C)C1=NC(C=2C=C(F)C=CC=2)=CN1CC1=CC=CC=C1 YCKIVXRVVNMXIK-IGKIAQTJSA-N 0.000 claims 1
- VBTLXHAPYJOERV-RPLLCQBOSA-N n-[(3s)-3-amino-4-methoxybutyl]-n-[(1r)-1-[4-(3-chlorophenyl)-1-[(3-fluorophenyl)methyl]imidazol-2-yl]-2-methylpropyl]-2-methoxyacetamide Chemical compound COC[C@@H](N)CCN(C(=O)COC)[C@H](C(C)C)C1=NC(C=2C=C(Cl)C=CC=2)=CN1CC1=CC=CC(F)=C1 VBTLXHAPYJOERV-RPLLCQBOSA-N 0.000 claims 1
- IOZZYJCJAMIQMP-IGKIAQTJSA-N n-[(3s)-3-amino-4-methoxybutyl]-n-[(1r)-1-[4-(3-fluorophenyl)-1-[(3-fluorophenyl)methyl]imidazol-2-yl]-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound COC[C@@H](N)CCN(C(=O)COC)[C@H](C(C)(C)C)C1=NC(C=2C=C(F)C=CC=2)=CN1CC1=CC=CC(F)=C1 IOZZYJCJAMIQMP-IGKIAQTJSA-N 0.000 claims 1
- UEWJIRMMZRGAEE-SIBVEZHUSA-N n-[(3s)-3-aminobutyl]-n-[(1r)-1-[1-benzyl-4-(2,5-difluorophenyl)imidazol-2-yl]-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound COCC(=O)N(CC[C@H](C)N)[C@H](C(C)(C)C)C1=NC(C=2C(=CC=C(F)C=2)F)=CN1CC1=CC=CC=C1 UEWJIRMMZRGAEE-SIBVEZHUSA-N 0.000 claims 1
- SJSLQVAPQCYQHF-SIBVEZHUSA-N n-[(3s)-3-aminobutyl]-n-[(1r)-1-[4-(3-fluorophenyl)-1-[(3-fluorophenyl)methyl]imidazol-2-yl]-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound COCC(=O)N(CC[C@H](C)N)[C@H](C(C)(C)C)C1=NC(C=2C=C(F)C=CC=2)=CN1CC1=CC=CC(F)=C1 SJSLQVAPQCYQHF-SIBVEZHUSA-N 0.000 claims 1
- USKQPSPUWKQOJK-SANMLTNESA-N n-[2-(1-aminocyclopropyl)ethyl]-n-[(1r)-1-(1-benzyl-4-phenylimidazol-2-yl)-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound COCC(=O)N([C@@H](C=1N(C=C(N=1)C=1C=CC=CC=1)CC=1C=CC=CC=1)C(C)(C)C)CCC1(N)CC1 USKQPSPUWKQOJK-SANMLTNESA-N 0.000 claims 1
- OOZZWLVAHWBNKE-SANMLTNESA-N n-[2-(1-aminocyclopropyl)ethyl]-n-[(1r)-1-[1-benzyl-4-(3-fluorophenyl)imidazol-2-yl]-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound COCC(=O)N([C@@H](C=1N(C=C(N=1)C=1C=C(F)C=CC=1)CC=1C=CC=CC=1)C(C)(C)C)CCC1(N)CC1 OOZZWLVAHWBNKE-SANMLTNESA-N 0.000 claims 1
- CBKFINYBZSPIST-MHZLTWQESA-N n-[3-(dimethylamino)propyl]-n-[(1r)-1-[4-(3-fluorophenyl)-1-[(3-fluorophenyl)methyl]imidazol-2-yl]-2,2-dimethylpropyl]-2-methoxyacetamide Chemical compound CN(C)CCCN(C(=O)COC)[C@H](C(C)(C)C)C1=NC(C=2C=C(F)C=CC=2)=CN1CC1=CC=CC(F)=C1 CBKFINYBZSPIST-MHZLTWQESA-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
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 1
- 229940080818 propionamide Drugs 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000003003 spiro group Chemical group 0.000 claims 1
- 125000003666 tauryl group Chemical group [H]N([H])C([H])([H])C([H])([H])S(*)(=O)=O 0.000 claims 1
- SVDVJTFCTUHZDG-QFIPXVFZSA-N tert-butyl n-[(1r)-1-[1-benzyl-4-(2,5-difluorophenyl)imidazol-2-yl]-2,2-dimethylpropyl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@H](C(C)(C)C)C1=NC(C=2C(=CC=C(F)C=2)F)=CN1CC1=CC=CC=C1 SVDVJTFCTUHZDG-QFIPXVFZSA-N 0.000 claims 1
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims 1
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims 1
- 125000002114 valyl group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 abstract 5
- 150000002460 imidazoles Chemical class 0.000 abstract 2
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229940121649 protein inhibitor Drugs 0.000 abstract 1
- 239000012268 protein inhibitor Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D233/24—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/10—Spiro-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US58092704P | 2004-06-18 | 2004-06-18 | |
| US60/580,927 | 2004-06-18 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2007101612A RU2007101612A (ru) | 2008-08-10 |
| RU2427572C2 true RU2427572C2 (ru) | 2011-08-27 |
Family
ID=34980173
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2007101612/04A RU2427572C2 (ru) | 2004-06-18 | 2005-06-20 | N-(1-(1-бензил-4-фенил-1н-имидазол-2-ил)-2,2-диметилпропил)бензамидные производные и родственные соединения в качестве ингибиторов кинезинового белка веретена (ksp) для лечения рака |
Country Status (21)
| Country | Link |
|---|---|
| US (3) | US7576221B2 (enExample) |
| EP (1) | EP1765789B1 (enExample) |
| JP (2) | JP4836280B2 (enExample) |
| KR (1) | KR101170925B1 (enExample) |
| CN (1) | CN1993331A (enExample) |
| AU (1) | AU2005258135B2 (enExample) |
| BR (1) | BRPI0510929A (enExample) |
| CA (1) | CA2571002A1 (enExample) |
| EC (1) | ECSP077183A (enExample) |
| ES (1) | ES2409345T3 (enExample) |
| IL (1) | IL180147A0 (enExample) |
| MA (1) | MA28739B1 (enExample) |
| MX (1) | MXPA06014909A (enExample) |
| NO (1) | NO20070343L (enExample) |
| NZ (1) | NZ552510A (enExample) |
| RU (1) | RU2427572C2 (enExample) |
| SG (1) | SG153851A1 (enExample) |
| TN (1) | TNSN06419A1 (enExample) |
| TW (1) | TW200612958A (enExample) |
| WO (1) | WO2006002236A1 (enExample) |
| ZA (1) | ZA200700481B (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2698697C2 (ru) * | 2013-12-23 | 2019-08-29 | Байер Фарма Акциенгезельшафт | Конъюгаты связующего (ADC) с ингибиторами KSP |
| RU2751512C2 (ru) * | 2015-06-22 | 2021-07-14 | Байер Фарма Акциенгезельшафт | Конъюгаты антитела и лекарственного средства (adc) и конъюгаты антитела и пролекарства (apdc), содержащие ферментативно расщепляемые группы |
| RU2761390C2 (ru) * | 2016-12-21 | 2021-12-07 | Байер Фарма Акциенгезельшафт | Конъюгаты связующего и активного вещества (adc), имеющие ферментативно расщепляемые группы |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7576221B2 (en) * | 2004-06-18 | 2009-08-18 | Novartis Vaccines And Diagnostics, Inc. | Substituted imidazole derivatives |
| UY29070A1 (es) | 2004-08-18 | 2006-03-31 | Astrazeneca Ab | Enantiómeros de heterocíclicos fusionados y sus usos |
| WO2007011647A2 (en) * | 2005-07-15 | 2007-01-25 | Kalypsys, Inc. | Inhibitors of mitotic kinesin ksp |
| TW200800951A (en) * | 2005-08-09 | 2008-01-01 | Novartis Ag | Substituted imidazole compounds as KSP inhibitors |
| US8119655B2 (en) | 2005-10-07 | 2012-02-21 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
| PE20080359A1 (es) | 2006-04-19 | 2008-06-06 | Novartis Ag | Compuestos de benzoxazol y benzotiazol 6-0-sustituidos y metodos de inhibicion de la senalizacion de csf-1r |
| EP2090570B1 (en) | 2006-09-05 | 2011-11-09 | Kyowa Hakko Kirin Co., Ltd. | Imidazole derivative |
| JP2010505962A (ja) | 2006-10-09 | 2010-02-25 | 武田薬品工業株式会社 | キナーゼ阻害剤 |
| US7902240B2 (en) * | 2006-11-13 | 2011-03-08 | Novartis Ag | Substituted pyrazole and triazole compounds as KSP inhibitors |
| EP2106399A2 (en) * | 2007-01-05 | 2009-10-07 | Novartis AG | Imidazole derivatives as kinesin spindle protein inhibitors (eg-5) |
| US8252832B2 (en) | 2007-12-14 | 2012-08-28 | Novartis Ag | Kinesin inhibitors as cancer therapeutics |
| US20110275685A1 (en) | 2009-01-26 | 2011-11-10 | Michael Mutz | Salt and polymorphs of a kinesin inhibitor compound |
| KR20130100056A (ko) * | 2010-04-15 | 2013-09-09 | 노파르티스 아게 | Ksp 억제제로서의 트리아졸 화합물 |
| US8748626B2 (en) | 2010-04-15 | 2014-06-10 | Novartis Ag | Oxazole and thiazole compounds as KSP inhibitors |
| DE102010025663A1 (de) | 2010-06-30 | 2012-01-05 | Karl-Heinz Glüsenkamp | Neue beta-Aminoaldehyd-Derivate, Verfahren zu ihrer Herstellung und ihre chemische Verwendung als reaktive Intermediate |
| US8809372B2 (en) | 2011-09-30 | 2014-08-19 | Asana Biosciences, Llc | Pyridine derivatives |
| WO2014151030A1 (en) * | 2013-03-15 | 2014-09-25 | Novartis Ag | Cell proliferation inhibitors and conjugates thereof |
| US9498540B2 (en) | 2013-03-15 | 2016-11-22 | Novartis Ag | Cell proliferation inhibitors and conjugates thereof |
| WO2016020791A1 (en) | 2014-08-05 | 2016-02-11 | Novartis Ag | Ckit antibody drug conjugates |
| CA2970565A1 (en) | 2014-12-15 | 2016-06-23 | Bayer Pharma Aktiengesellschaft | Antibody-drug conjugates (adcs) of ksp inhibitors with aglycosylated anti-tweakr antibodies |
| IS2977B (is) | 2015-02-23 | 2017-07-15 | Actavis Group Ptc Ehf. | Aðferð til framleiðslu á milliefnum sem eru nytsamleg við nýsmíði á elúxadólíni |
| JP2018525334A (ja) | 2015-06-23 | 2018-09-06 | バイエル ファーマ アクチエンゲゼルシャフト | キネシンスピンドルタンパク質(ksp)阻害剤の抗tweakr抗体との抗体薬物複合体 |
| CA2990300A1 (en) | 2015-06-23 | 2016-12-29 | Hans-Georg Lerchen | Site specific homogeneous conjugates with ksp inhibitors |
| CA2990411A1 (en) | 2015-06-23 | 2016-12-29 | Bayer Pharma Aktiengesellschaft | Antibody drug conjugates of kinesin spindel protein (ksp) inhibitors with anti-b7h3-antibodies |
| CA3027445A1 (en) | 2016-06-15 | 2017-12-21 | Bayer Pharma Aktiengesellschaft | Specific antibody-drug-conjugates (adcs) with ksp inhibitors and anti-cd123-antibodies |
| WO2018114804A1 (de) | 2016-12-21 | 2018-06-28 | Bayer Pharma Aktiengesellschaft | Spezifische antikörper-wirkstoff-konjugate (adcs) mit ksp-inhibitoren |
| CN112601553A (zh) | 2018-06-18 | 2021-04-02 | 拜耳股份有限公司 | 具有可酶切的接头和改善的活性谱的针对cxcr5的结合剂-药物缀合物 |
| CA3123871A1 (en) | 2018-12-20 | 2020-06-25 | Amgen Inc. | Kif18a inhibitors |
| TW202317092A (zh) | 2021-08-26 | 2023-05-01 | 美商佛拉斯托醫療公司 | Kif18a之吲哚啉抑制劑 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2216541C2 (ru) * | 1998-08-04 | 2003-11-20 | Астразенека Аб | Производные бензамида, способ их получения и фармацевтическая композиция на их основе |
| RU2219171C2 (ru) * | 1998-09-25 | 2003-12-20 | Астразенека Аб | Производные амида, способ их получения и фармацевтическая композиция на их основе |
Family Cites Families (63)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2550959C3 (de) * | 1975-11-13 | 1980-12-04 | Hoechst Ag, 6000 Frankfurt | Tetrazolyl-imidazole und Tetrazolyl--benzimidazole, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel |
| WO1998027108A2 (en) | 1996-12-16 | 1998-06-25 | Fujisawa Pharmaceutical Co., Ltd. | New amide compounds and their use as nitric oxide synthase inhibitors |
| US6117940A (en) | 1997-10-17 | 2000-09-12 | Mjalli; Adnan M. M. | Amino-ketone solid support templates |
| CA2369549A1 (en) | 1999-04-02 | 2000-10-12 | Robert W. Desimone | Aryl and heteroaryl fused aminoalkyl-imidazole derivatives and their use as antidiabetics |
| US7291641B2 (en) * | 1999-10-11 | 2007-11-06 | Societe De Conseils De Recherches Et D'applications Scientifiques (S.C.R.A.S.) | Derivatives of heterocycles with 5 members, their preparation and their use as medicaments |
| US20040132788A1 (en) * | 1999-10-11 | 2004-07-08 | Chabrier De Lassauniere Pierre-Etienne | Derivatives of heterocycles with 5 members, their preparation and their use as medicaments |
| TWI292316B (en) * | 1999-10-11 | 2008-01-11 | Sod Conseils Rech Applic | Pharmaceutical composition of thiazole derivatives intended to inhibit mao and/or lipidic peroxidation and/or to act as modulators of sodium channels and the use thereof |
| US6545004B1 (en) * | 1999-10-27 | 2003-04-08 | Cytokinetics, Inc. | Methods and compositions utilizing quinazolinones |
| EP1686120A3 (en) | 1999-10-27 | 2007-05-30 | Cytokinetics, Inc. | Methods and compositions utilizing quinazolinones |
| US6620882B1 (en) | 2000-05-02 | 2003-09-16 | Advanced Syntech, Llc | Solid support template for preparation of highly functionalized heterocycle compounds |
| US6683191B2 (en) | 2000-06-05 | 2004-01-27 | Ortho-Mcneil Pharmaceuticals, Inc. | Method for synthesis of substituted azole libraries |
| US6951948B2 (en) | 2000-06-05 | 2005-10-04 | Ortho-Mcneil Pharmaceutical, Inc. | Method for synthesis of substituted azole libraries |
| KR20030020960A (ko) * | 2000-08-01 | 2003-03-10 | 소시에떼 더 콘세이유 더 레세르세 에 다플리까띠옹 시엔띠피끄, 에스.아.에스. | 이미다졸일 유도체 |
| WO2002028839A1 (en) | 2000-10-06 | 2002-04-11 | Neurogen Corporation | Benzimidazole and indole derivatives as crf receptor modulators |
| JP2002190437A (ja) | 2000-12-20 | 2002-07-05 | Advantest Corp | 電子ビーム露光装置及び校正方法 |
| WO2002056880A1 (en) | 2001-01-19 | 2002-07-25 | Cytokinetics, Inc. | Triphenylmethane kinesin inhibitors |
| US6992082B2 (en) | 2001-01-19 | 2006-01-31 | Cytokinetics, Inc. | Phenothiazine kinesin inhibitors |
| US6610723B2 (en) * | 2001-01-29 | 2003-08-26 | Hoffmann-La Roche Inc. | Imidazole derivatives |
| US7049303B2 (en) | 2001-11-07 | 2006-05-23 | Medical Research Council | Inhibition of viruses |
| US7060705B2 (en) | 2001-11-07 | 2006-06-13 | Merck & Co., Inc. | Mitotic kinesin inhibitors |
| WO2003043995A1 (en) | 2001-11-20 | 2003-05-30 | Cytokinetics, Inc. | Process for the racemization of chiral quinazolinones |
| US7244723B2 (en) | 2001-12-06 | 2007-07-17 | Merck & Co., Inc. | Substituted furopyrimidinones as a mitotic kinesin inhibitors |
| CA2467916A1 (en) | 2001-12-06 | 2003-06-19 | Merck & Co., Inc. | Mitotic kinesin inhibitors |
| JP4391825B2 (ja) | 2001-12-06 | 2009-12-24 | メルク エンド カムパニー インコーポレーテッド | 有糸分裂キネシン阻害剤 |
| EP1481077B1 (en) * | 2001-12-06 | 2009-11-04 | Merck & Co., Inc. | Mitotic kinesin inhibitors |
| US7378411B2 (en) | 2001-12-06 | 2008-05-27 | Merck & Co., Inc. | Substituted thienopyrimidinones as a mitotic kinesin inhibitor |
| US6906075B2 (en) | 2002-01-10 | 2005-06-14 | Neurogen Corp. | Melanin concentrating hormone receptor ligands: substituted benzoimidazole analogues |
| US7009049B2 (en) | 2002-02-15 | 2006-03-07 | Cytokinetics, Inc. | Syntheses of quinazolinones |
| CA2478068C (en) | 2002-03-08 | 2011-02-08 | Merck & Co., Inc. | Dihydropyrazole compounds useful for treating or preventing cancer |
| US7026312B2 (en) * | 2002-03-14 | 2006-04-11 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Substituted piperidines, pharmaceutical compositions containing these compounds, their use and processes for the preparation thereof |
| DE10211770A1 (de) | 2002-03-14 | 2003-10-02 | Boehringer Ingelheim Pharma | Neue substituierte Piperidine, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
| AU2003245259A1 (en) | 2002-05-02 | 2003-11-17 | Neurogen Corporation | Substituted imidazole derivatives: gabaa receptor ligands |
| US6982268B2 (en) | 2002-05-08 | 2006-01-03 | Neurogen Corporation | Substituted imidazolylmethyl pyridine and pyrazine derivatives GABAA receptor ligands |
| US7214800B2 (en) | 2002-05-09 | 2007-05-08 | Cytokinetics, Inc. | Compounds, compositions, and methods |
| US7166595B2 (en) * | 2002-05-09 | 2007-01-23 | Cytokinetics, Inc. | Compounds, methods and compositions |
| EP1507534A4 (en) | 2002-05-10 | 2006-11-08 | Cytokinetics Inc | COMPOUNDS, COMPOSITIONS AND METHODS |
| CA2486339A1 (en) | 2002-05-17 | 2003-11-27 | Neurogen Corporation | Substituted ring-fused imidazole derivates: gabaa receptor ligands |
| US7038048B2 (en) * | 2002-05-23 | 2006-05-02 | Cytokinetics, Inc. | 3H-pyridopyrimidin-4-one compounds, compositions, and methods of their use |
| AU2003231799A1 (en) | 2002-05-23 | 2003-12-12 | Merck & Co., Inc. | Mitotic kinesin inhibitors |
| JP4463679B2 (ja) | 2002-06-14 | 2010-05-19 | メルク エンド カムパニー インコーポレーテッド | 有糸分裂キネシン阻害剤 |
| JP4377323B2 (ja) | 2002-06-14 | 2009-12-02 | メルク エンド カムパニー インコーポレーテッド | 有糸分裂キネシン阻害剤 |
| WO2004001489A1 (ja) | 2002-06-19 | 2003-12-31 | Mitsubishi Denki Kabushiki Kaisha | 光変調器 |
| EP1551962A4 (en) | 2002-07-08 | 2007-08-01 | Merck & Co Inc | MITOTIC KINESIN BINDING CENTER |
| RU2233736C2 (ru) | 2002-07-11 | 2004-08-10 | Раховский Вадим Израилович | Нанометрическое позиционирующее устройство |
| DE60326248D1 (de) | 2002-07-17 | 2009-04-02 | Cytokinetics Inc | Verbindungen, zusammensetzungen und verfahren zur behandlung von zellulären proliferativen erkrankungen |
| JP2006501201A (ja) | 2002-07-23 | 2006-01-12 | 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 |
| KR100492252B1 (ko) | 2002-08-09 | 2005-05-30 | 한국화학연구원 | 이미다졸을 포함하는 이차아민으로 치환된 벤조피란유도체 및 그의 제조방법 |
| EP1539180A4 (en) | 2002-08-21 | 2006-08-30 | Cytokinetics Inc | COMPOUNDS, COMPOSITIONS AND METHODS |
| WO2004024086A2 (en) | 2002-09-13 | 2004-03-25 | Cytokinetics, Inc. | Compounds, compositions and methods |
| WO2004026859A1 (en) | 2002-09-18 | 2004-04-01 | Pfizer Products Inc. | Novel imidazole compounds as transforming growth factor (tgf) inhibitors |
| EP1558083A4 (en) * | 2002-09-30 | 2008-04-16 | Cytokinetics Inc | COMPOUNDS, COMPOSITIONS AND METHODS |
| CN100579579C (zh) | 2002-10-01 | 2010-01-13 | 诺华疫苗和诊断公司 | 抗癌及抗感染性疾病组合物及其使用方法 |
| MXPA05003830A (es) * | 2002-10-11 | 2005-06-23 | Cytokinetics Inc | Compuestos, composiciones y metodos. |
| JP2006508102A (ja) | 2002-11-08 | 2006-03-09 | ニューロジェン・コーポレイション | Gabaa受容体のリガンドとしての4−イミダゾール−1−イルメチル−ピリミジン誘導体 |
| US20040186151A1 (en) | 2003-02-12 | 2004-09-23 | Mjalli Adnan M.M. | Substituted azole derivatives as therapeutic agents |
| US7662581B1 (en) * | 2003-12-18 | 2010-02-16 | Novartis Vaccines And Diagnostics, Inc. | Eg5 co-crystals |
| DE602005016775D1 (de) | 2004-01-16 | 2009-11-05 | Wyeth Corp | Heterocyclische, ein azol enthaltende sulfonamidinhibitoren der beta-amyloid-produktion |
| AU2005214349B2 (en) * | 2004-02-12 | 2011-11-03 | Transtech Pharma, Inc. | Substituted azole derivatives, compositions, and methods of use |
| JP4895220B2 (ja) * | 2004-04-06 | 2012-03-14 | ノバルティス バクシンズ アンド ダイアグノスティックス,インコーポレーテッド | キネシン有糸分裂インヒビター |
| US20080132549A1 (en) | 2004-04-14 | 2008-06-05 | Pfizer Inc. | Sulphur-Linked Imidazone Compounds for the Treatment of Hiv/Aids |
| US7592453B2 (en) | 2004-04-28 | 2009-09-22 | Takeda Pharmaceutical Company Limited | Fused quinoline derivative and use thereof |
| US7618981B2 (en) | 2004-05-06 | 2009-11-17 | Cytokinetics, Inc. | Imidazopyridinyl-benzamide anti-cancer agents |
| US7576221B2 (en) * | 2004-06-18 | 2009-08-18 | Novartis Vaccines And Diagnostics, Inc. | Substituted imidazole derivatives |
-
2005
- 2005-06-20 US US11/158,574 patent/US7576221B2/en not_active Expired - Fee Related
- 2005-06-20 BR BRPI0510929-9A patent/BRPI0510929A/pt not_active IP Right Cessation
- 2005-06-20 CA CA002571002A patent/CA2571002A1/en not_active Abandoned
- 2005-06-20 WO PCT/US2005/022062 patent/WO2006002236A1/en not_active Ceased
- 2005-06-20 AU AU2005258135A patent/AU2005258135B2/en not_active Ceased
- 2005-06-20 SG SG200904294-6A patent/SG153851A1/en unknown
- 2005-06-20 MX MXPA06014909A patent/MXPA06014909A/es active IP Right Grant
- 2005-06-20 KR KR1020077000979A patent/KR101170925B1/ko not_active Expired - Fee Related
- 2005-06-20 CN CNA2005800262037A patent/CN1993331A/zh active Pending
- 2005-06-20 EP EP05760871A patent/EP1765789B1/en not_active Expired - Lifetime
- 2005-06-20 RU RU2007101612/04A patent/RU2427572C2/ru not_active IP Right Cessation
- 2005-06-20 JP JP2007516842A patent/JP4836280B2/ja not_active Expired - Fee Related
- 2005-06-20 TW TW094120475A patent/TW200612958A/zh unknown
- 2005-06-20 NZ NZ552510A patent/NZ552510A/en not_active IP Right Cessation
- 2005-06-20 ES ES05760871T patent/ES2409345T3/es not_active Expired - Lifetime
-
2006
- 2006-12-18 TN TNP2006000419A patent/TNSN06419A1/en unknown
- 2006-12-18 IL IL180147A patent/IL180147A0/en unknown
-
2007
- 2007-01-16 ZA ZA200700481A patent/ZA200700481B/xx unknown
- 2007-01-17 MA MA29617A patent/MA28739B1/fr unknown
- 2007-01-18 NO NO20070343A patent/NO20070343L/no not_active Application Discontinuation
- 2007-01-18 EC EC2007007183A patent/ECSP077183A/es unknown
-
2009
- 2009-06-05 US US12/455,798 patent/US8318791B2/en not_active Expired - Fee Related
-
2011
- 2011-08-18 JP JP2011179247A patent/JP2011256197A/ja not_active Withdrawn
-
2012
- 2012-09-13 US US13/613,977 patent/US8735599B2/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2216541C2 (ru) * | 1998-08-04 | 2003-11-20 | Астразенека Аб | Производные бензамида, способ их получения и фармацевтическая композиция на их основе |
| RU2219171C2 (ru) * | 1998-09-25 | 2003-12-20 | Астразенека Аб | Производные амида, способ их получения и фармацевтическая композиция на их основе |
Non-Patent Citations (1)
| Title |
|---|
| DENG et al: "Synthetic Applications of Azolium Ylides to a Traceless Solid-Phase Synthesis of 2-Substituted Azoles", ORGANIC LETTERS, vol.4, no.23, 2002, pages 4017-4020. * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2698697C2 (ru) * | 2013-12-23 | 2019-08-29 | Байер Фарма Акциенгезельшафт | Конъюгаты связующего (ADC) с ингибиторами KSP |
| RU2751512C2 (ru) * | 2015-06-22 | 2021-07-14 | Байер Фарма Акциенгезельшафт | Конъюгаты антитела и лекарственного средства (adc) и конъюгаты антитела и пролекарства (apdc), содержащие ферментативно расщепляемые группы |
| RU2761390C2 (ru) * | 2016-12-21 | 2021-12-07 | Байер Фарма Акциенгезельшафт | Конъюгаты связующего и активного вещества (adc), имеющие ферментативно расщепляемые группы |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2006002236A1 (en) | 2006-01-05 |
| KR20070106961A (ko) | 2007-11-06 |
| EP1765789A1 (en) | 2007-03-28 |
| NO20070343L (no) | 2007-03-05 |
| JP4836280B2 (ja) | 2011-12-14 |
| BRPI0510929A (pt) | 2007-07-17 |
| MA28739B1 (fr) | 2007-07-02 |
| AU2005258135B2 (en) | 2011-09-22 |
| TW200612958A (en) | 2006-05-01 |
| EP1765789B1 (en) | 2013-02-27 |
| SG153851A1 (en) | 2009-07-29 |
| CA2571002A1 (en) | 2006-01-05 |
| ECSP077183A (es) | 2007-02-28 |
| IL180147A0 (en) | 2007-06-03 |
| US20130017196A1 (en) | 2013-01-17 |
| US20060009472A1 (en) | 2006-01-12 |
| NZ552510A (en) | 2010-12-24 |
| CN1993331A (zh) | 2007-07-04 |
| ZA200700481B (en) | 2008-10-29 |
| US8735599B2 (en) | 2014-05-27 |
| AU2005258135A1 (en) | 2006-01-05 |
| RU2007101612A (ru) | 2008-08-10 |
| JP2011256197A (ja) | 2011-12-22 |
| ES2409345T3 (es) | 2013-06-26 |
| US7576221B2 (en) | 2009-08-18 |
| JP2008503501A (ja) | 2008-02-07 |
| US20090258016A1 (en) | 2009-10-15 |
| TNSN06419A1 (en) | 2008-02-22 |
| KR101170925B1 (ko) | 2012-08-07 |
| US8318791B2 (en) | 2012-11-27 |
| MXPA06014909A (es) | 2007-02-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2427572C2 (ru) | N-(1-(1-бензил-4-фенил-1н-имидазол-2-ил)-2,2-диметилпропил)бензамидные производные и родственные соединения в качестве ингибиторов кинезинового белка веретена (ksp) для лечения рака | |
| JP2008503501A5 (enExample) | ||
| CA2575003A1 (en) | Potassium channel inhibitors | |
| ES2557478T3 (es) | Compuestos de pirazol y triazol como inhibidores de KSP | |
| JP2014521696A5 (enExample) | ||
| RU2006127573A (ru) | Соединения тетразола и их применение в качестве антагонистов метаботропного рецептора глутамата | |
| RU2009147733A (ru) | Пиридилпиперидновые антагонисты рецептора орексинов | |
| RU2016133684A (ru) | Бициклические азот-содержащие соединения как агонисты М1 мускариновых рецепторов | |
| SK283555B6 (sk) | 1-(1,2-Disubstituovaný piperidinyl)-4-substituované deriváty piperidínu, spôsob ich výroby, ich použitie a farmaceutické prostriedky na ich báze | |
| RU2008120619A (ru) | (гетеро)арилы, обладающие антагонистической активностью по отношению к меланинконцентрирующему гормону | |
| USRE49700E1 (en) | Substituted nitrogen containing compounds | |
| JP2017500364A5 (enExample) | ||
| JP2017502049A5 (enExample) | ||
| RU2009110446A (ru) | Новые производные пиридона, обладающие антагонистической активностью в отношении mch, и лекарственные средства, включающие такие соединения | |
| RU2006145205A (ru) | Терапевтические соединения: пиридин в качестве каркаса | |
| JPWO2020201773A5 (enExample) | ||
| RU2015144485A (ru) | Геминально-замещенные цианоэтилпиразолопиридоны в качестве ингибиторов janus киназ | |
| RU2007104838A (ru) | 2,4,6-тризамещенные пиримидины в качестве ингибиторовфосфотидилинозитол (pi) 3-киназы и их применение для лечения злокачественного новообразования | |
| JP2009504664A5 (enExample) | ||
| RU2008108939A (ru) | Замещенные имидазолы, фармацевтическая композиция, способ лечения заболевания, связанного по крайней мере с активностью ksp, способ ингибирования ksp, лекарственное средство для лечения рака | |
| JPWO2019147782A5 (enExample) | ||
| RU2005100783A (ru) | Ингибиторы митотического кинезина | |
| RU2025118628A (ru) | Новые соединения в качестве модуляторов ингибирования nlrp3 | |
| RU2021111663A (ru) | Соединение аминопиримидина | |
| NZ734260B2 (en) | Substituted triazoles and methods relating thereto |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20130621 |