HRP20110312T1 - Supstituirani benzimidazoli i postupci pripreme - Google Patents

Supstituirani benzimidazoli i postupci pripreme Download PDF

Info

Publication number: HRP20110312T1
Authority: HR; Croatia
Prior art keywords: trifluoromethyl; methyl; phenyl; pyridin; compound
Prior art date: 2005-08-30

Application number

HR20110312T

Other languages

English (en)

Croatian (hr)

Inventor

Dimitroff Martin

R. Miller Bridget

S. Stillwell Brady

A. Siesel David

Swiftney Tyson

Diaz Brian

Gu Danlin

P. Van Dyck Jonathan

Ryckman David

J. Poon Daniel

E. Pick Teresa

Original Assignee

Novartis Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2005-08-30

Filing date

2011-04-29

Publication date

2011-08-31

2011-04-29 Application filed by Novartis Ag filed Critical Novartis Ag

2011-08-31 Publication of HRP20110312T1 publication Critical patent/HRP20110312T1/hr

Links

238000000034 method Methods 0.000 title claims abstract 21
150000001556 benzimidazoles Chemical class 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract 66
125000000217 alkyl group Chemical group 0.000 claims abstract 26
125000001475 halogen functional group Chemical group 0.000 claims abstract 24
125000003545 alkoxy group Chemical group 0.000 claims abstract 18
150000003839 salts Chemical class 0.000 claims abstract 12
125000004093 cyano group Chemical group *C#N 0.000 claims abstract 11
125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract 11
125000000753 cycloalkyl group Chemical group 0.000 claims abstract 6
150000002148 esters Chemical class 0.000 claims abstract 6
125000001072 heteroaryl group Chemical group 0.000 claims abstract 6
125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 6
229940002612 prodrug Drugs 0.000 claims abstract 6
239000000651 prodrug Substances 0.000 claims abstract 6
125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims abstract 4
239000003795 chemical substances by application Substances 0.000 claims abstract 4
230000003009 desulfurizing effect Effects 0.000 claims abstract 4
125000000524 functional group Chemical group 0.000 claims abstract 4
LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims abstract 3
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims abstract 3
150000001450 anions Chemical class 0.000 claims abstract 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 3
238000006798 ring closing metathesis reaction Methods 0.000 claims abstract 3
125000001424 substituent group Chemical group 0.000 claims abstract 3
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract 3
125000003396 thiol group Chemical group [H]S* 0.000 claims abstract 3
239000002253 acid Substances 0.000 claims abstract 2
229910052739 hydrogen Inorganic materials 0.000 claims abstract 2
239000001257 hydrogen Substances 0.000 claims abstract 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 2
125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims abstract 2
125000002883 imidazolyl group Chemical group 0.000 claims abstract 2
125000006239 protecting group Chemical group 0.000 claims abstract 2
238000007363 ring formation reaction Methods 0.000 claims abstract 2
239000003638 chemical reducing agent Substances 0.000 claims 4
239000002798 polar solvent Substances 0.000 claims 4
-1 3-trifluoromethyl-phenyl Chemical group 0.000 claims 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
238000006243 chemical reaction Methods 0.000 claims 3
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
150000007529 inorganic bases Chemical class 0.000 claims 2
JDAPYAFPVKVBPF-UHFFFAOYSA-N n-(2-fluoro-5-pyridin-3-ylphenyl)-1-methyl-5-[2-[5-(trifluoromethyl)-1h-imidazol-2-yl]pyridin-4-yl]oxybenzimidazol-2-amine Chemical compound N=1C2=CC(OC=3C=C(N=CC=3)C=3NC(=CN=3)C(F)(F)F)=CC=C2N(C)C=1NC(C(=CC=1)F)=CC=1C1=CC=CN=C1 JDAPYAFPVKVBPF-UHFFFAOYSA-N 0.000 claims 2
NVKYHJWQISEJQK-UHFFFAOYSA-N n-(2-fluoro-5-pyridin-4-ylphenyl)-1-methyl-5-[2-[5-(trifluoromethyl)-1h-imidazol-2-yl]pyridin-4-yl]oxybenzimidazol-2-amine Chemical compound N=1C2=CC(OC=3C=C(N=CC=3)C=3NC(=CN=3)C(F)(F)F)=CC=C2N(C)C=1NC(C(=CC=1)F)=CC=1C1=CC=NC=C1 NVKYHJWQISEJQK-UHFFFAOYSA-N 0.000 claims 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
BPMDDRXOVIYKRO-UHFFFAOYSA-N (4-ethylpiperazin-1-yl)-[2-[4-[1-methyl-2-[4-(trifluoromethyl)anilino]benzimidazol-5-yl]oxypyridin-2-yl]-1h-imidazol-5-yl]methanone Chemical compound C1CN(CC)CCN1C(=O)C1=CN=C(C=2N=CC=C(OC=3C=C4N=C(NC=5C=CC(=CC=5)C(F)(F)F)N(C)C4=CC=3)C=2)N1 BPMDDRXOVIYKRO-UHFFFAOYSA-N 0.000 claims 1
RUQDVCHGGJZPBP-UHFFFAOYSA-N (4-ethylpiperazin-1-yl)-[2-[4-[2-[2-fluoro-5-(trifluoromethyl)anilino]-1-methylbenzimidazol-5-yl]oxypyridin-2-yl]-1h-imidazol-5-yl]methanone Chemical compound C1CN(CC)CCN1C(=O)C1=CN=C(C=2N=CC=C(OC=3C=C4N=C(NC=5C(=CC=C(C=5)C(F)(F)F)F)N(C)C4=CC=3)C=2)N1 RUQDVCHGGJZPBP-UHFFFAOYSA-N 0.000 claims 1
QQZNCAXYRMMAFQ-UHFFFAOYSA-N 1-ethyl-5-[2-[5-(trifluoromethyl)-1h-imidazol-2-yl]pyridin-4-yl]oxy-n-[4-(trifluoromethyl)phenyl]benzimidazol-2-amine Chemical compound N=1C2=CC(OC=3C=C(N=CC=3)C=3NC(=CN=3)C(F)(F)F)=CC=C2N(CC)C=1NC1=CC=C(C(F)(F)F)C=C1 QQZNCAXYRMMAFQ-UHFFFAOYSA-N 0.000 claims 1
LVNYFIASUPVQIV-UHFFFAOYSA-N 1-methyl-5-[2-(5-phenyl-1h-imidazol-2-yl)pyridin-4-yl]oxy-n-[4-(trifluoromethylsulfanyl)phenyl]benzimidazol-2-amine Chemical compound N=1C2=CC(OC=3C=C(N=CC=3)C=3NC(=CN=3)C=3C=CC=CC=3)=CC=C2N(C)C=1NC1=CC=C(SC(F)(F)F)C=C1 LVNYFIASUPVQIV-UHFFFAOYSA-N 0.000 claims 1
ADEVTABMDFBPPG-UHFFFAOYSA-N 1-methyl-5-[2-[5-(trifluoromethyl)-1h-imidazol-2-yl]pyridin-4-yl]oxy-n-[2-(trifluoromethyl)phenyl]benzimidazol-2-amine Chemical compound N=1C2=CC(OC=3C=C(N=CC=3)C=3NC(=CN=3)C(F)(F)F)=CC=C2N(C)C=1NC1=CC=CC=C1C(F)(F)F ADEVTABMDFBPPG-UHFFFAOYSA-N 0.000 claims 1
DVJYMPYLFMEZMR-UHFFFAOYSA-N 1-methyl-5-[2-[5-(trifluoromethyl)-1h-imidazol-2-yl]pyridin-4-yl]oxy-n-[3-(trifluoromethyl)phenyl]benzimidazol-2-amine Chemical compound N=1C2=CC(OC=3C=C(N=CC=3)C=3NC(=CN=3)C(F)(F)F)=CC=C2N(C)C=1NC1=CC=CC(C(F)(F)F)=C1 DVJYMPYLFMEZMR-UHFFFAOYSA-N 0.000 claims 1
ZNKJEEFWTJMGCS-UHFFFAOYSA-N 1-methyl-5-[2-[5-(trifluoromethyl)-1h-imidazol-2-yl]pyridin-4-yl]oxy-n-[4-(trifluoromethylsulfanyl)phenyl]benzimidazol-2-amine Chemical compound N=1C2=CC(OC=3C=C(N=CC=3)C=3NC(=CN=3)C(F)(F)F)=CC=C2N(C)C=1NC1=CC=C(SC(F)(F)F)C=C1 ZNKJEEFWTJMGCS-UHFFFAOYSA-N 0.000 claims 1
YABJJWZLRMPFSI-UHFFFAOYSA-N 1-methyl-5-[[2-[5-(trifluoromethyl)-1H-imidazol-2-yl]-4-pyridinyl]oxy]-N-[4-(trifluoromethyl)phenyl]-2-benzimidazolamine Chemical compound N=1C2=CC(OC=3C=C(N=CC=3)C=3NC(=CN=3)C(F)(F)F)=CC=C2N(C)C=1NC1=CC=C(C(F)(F)F)C=C1 YABJJWZLRMPFSI-UHFFFAOYSA-N 0.000 claims 1
OZOMCNZBYFGHSP-UHFFFAOYSA-N 1-methyl-n-[4-(4-methylpiperazin-1-yl)phenyl]-5-[2-[5-(trifluoromethyl)-1h-imidazol-2-yl]pyridin-4-yl]oxybenzimidazol-2-amine Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC2=CC(OC=3C=C(N=CC=3)C=3NC(=CN=3)C(F)(F)F)=CC=C2N1C OZOMCNZBYFGHSP-UHFFFAOYSA-N 0.000 claims 1
XJDIHOYNBOTGEN-UHFFFAOYSA-N 1-methyl-n-[4-(trifluoromethoxy)phenyl]-5-[2-[5-(trifluoromethyl)-1h-imidazol-2-yl]pyridin-4-yl]oxybenzimidazol-2-amine Chemical compound N=1C2=CC(OC=3C=C(N=CC=3)C=3NC(=CN=3)C(F)(F)F)=CC=C2N(C)C=1NC1=CC=C(OC(F)(F)F)C=C1 XJDIHOYNBOTGEN-UHFFFAOYSA-N 0.000 claims 1
LQQRMHCFUPBXAK-UHFFFAOYSA-N 2-[4-[1-methyl-2-[4-(trifluoromethyl)anilino]benzimidazol-5-yl]oxypyridin-2-yl]-1h-imidazole-5-carbonitrile Chemical compound N=1C2=CC(OC=3C=C(N=CC=3)C=3NC(=CN=3)C#N)=CC=C2N(C)C=1NC1=CC=C(C(F)(F)F)C=C1 LQQRMHCFUPBXAK-UHFFFAOYSA-N 0.000 claims 1
OFYJNFTZWLQOFC-UHFFFAOYSA-N 2-[4-[2-[2-fluoro-5-(trifluoromethyl)anilino]-1-methylbenzimidazol-5-yl]oxypyridin-2-yl]-1h-imidazole-5-carbonitrile Chemical compound N=1C2=CC(OC=3C=C(N=CC=3)C=3NC(=CN=3)C#N)=CC=C2N(C)C=1NC1=CC(C(F)(F)F)=CC=C1F OFYJNFTZWLQOFC-UHFFFAOYSA-N 0.000 claims 1
MEGIOXIBNYRWDR-UHFFFAOYSA-N 2-[4-[2-[2-fluoro-5-(trifluoromethyl)anilino]-1-methylbenzimidazol-5-yl]oxypyridin-2-yl]-n-(2-hydroxyethyl)-1h-imidazole-5-carboxamide Chemical compound N=1C2=CC(OC=3C=C(N=CC=3)C=3NC(=CN=3)C(=O)NCCO)=CC=C2N(C)C=1NC1=CC(C(F)(F)F)=CC=C1F MEGIOXIBNYRWDR-UHFFFAOYSA-N 0.000 claims 1
OCZXHQKDRFDCRJ-UHFFFAOYSA-N 2-[[1-methyl-5-[2-[5-(trifluoromethyl)-1H-imidazol-2-yl]pyridin-4-yl]oxybenzimidazol-2-yl]amino]-5-(trifluoromethyl)phenol Chemical compound N=1C2=CC(OC=3C=C(N=CC=3)C=3NC(=CN=3)C(F)(F)F)=CC=C2N(C)C=1NC1=CC=C(C(F)(F)F)C=C1O OCZXHQKDRFDCRJ-UHFFFAOYSA-N 0.000 claims 1
RLRHXLXCAWJBGX-UHFFFAOYSA-N 2-chloro-1,3-dimethyl-1,2-dihydroimidazol-1-ium;chloride Chemical compound [Cl-].CN1C=C[NH+](C)C1Cl RLRHXLXCAWJBGX-UHFFFAOYSA-N 0.000 claims 1
KLTIMEXKPRJOIS-UHFFFAOYSA-N 2-chloro-1-methyl-2H-pyridine hydroiodide Chemical compound I.CN1C=CC=CC1Cl KLTIMEXKPRJOIS-UHFFFAOYSA-N 0.000 claims 1
125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 1
LEDHAWOWVPPJPN-UHFFFAOYSA-N 5-[[1-methyl-5-[2-[5-(trifluoromethyl)-1h-imidazol-2-yl]pyridin-4-yl]oxybenzimidazol-2-yl]amino]-2-(trifluoromethyl)phenol Chemical compound N=1C2=CC(OC=3C=C(N=CC=3)C=3NC(=CN=3)C(F)(F)F)=CC=C2N(C)C=1NC1=CC=C(C(F)(F)F)C(O)=C1 LEDHAWOWVPPJPN-UHFFFAOYSA-N 0.000 claims 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 1
229910021578 Iron(III) chloride Inorganic materials 0.000 claims 1
229910019213 POCl3 Inorganic materials 0.000 claims 1
SHWSLZQDDYQHGI-UHFFFAOYSA-N [2-[4-[2-[2-fluoro-5-(trifluoromethyl)anilino]-1-methylbenzimidazol-5-yl]oxypyridin-2-yl]-4-(trifluoromethyl)-1h-imidazol-5-yl]methanol Chemical compound N=1C2=CC(OC=3C=C(N=CC=3)C=3NC(=C(CO)N=3)C(F)(F)F)=CC=C2N(C)C=1NC1=CC(C(F)(F)F)=CC=C1F SHWSLZQDDYQHGI-UHFFFAOYSA-N 0.000 claims 1
235000011114 ammonium hydroxide Nutrition 0.000 claims 1
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical group CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 claims 1
235000010216 calcium carbonate Nutrition 0.000 claims 1
229910000019 calcium carbonate Inorganic materials 0.000 claims 1
UEOHBSPCKMVSEZ-UHFFFAOYSA-N ethyl 2-[4-[2-[2-chloro-5-(trifluoromethyl)anilino]-1-methylbenzimidazol-5-yl]oxypyridin-2-yl]-5-(trifluoromethyl)-1h-imidazole-4-carboxylate Chemical compound N1C(C(F)(F)F)=C(C(=O)OCC)N=C1C1=CC(OC=2C=C3N=C(NC=4C(=CC=C(C=4)C(F)(F)F)Cl)N(C)C3=CC=2)=CC=N1 UEOHBSPCKMVSEZ-UHFFFAOYSA-N 0.000 claims 1
XDYXHTQMOKHMDM-UHFFFAOYSA-N ethyl 2-[4-[2-[2-fluoro-5-(trifluoromethyl)anilino]-1-methylbenzimidazol-5-yl]oxypyridin-2-yl]-5-(trifluoromethyl)-1h-imidazole-4-carboxylate Chemical compound N1C(C(F)(F)F)=C(C(=O)OCC)N=C1C1=CC(OC=2C=C3N=C(NC=4C(=CC=C(C=4)C(F)(F)F)F)N(C)C3=CC=2)=CC=N1 XDYXHTQMOKHMDM-UHFFFAOYSA-N 0.000 claims 1
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims 1
BEOWSPCVIHQXLI-UHFFFAOYSA-N methyl 2-[4-[2-[2-fluoro-5-(trifluoromethyl)anilino]-1-methylbenzimidazol-5-yl]oxypyridin-2-yl]-1h-imidazole-5-carboxylate Chemical compound N1C(C(=O)OC)=CN=C1C1=CC(OC=2C=C3N=C(NC=4C(=CC=C(C=4)C(F)(F)F)F)N(C)C3=CC=2)=CC=N1 BEOWSPCVIHQXLI-UHFFFAOYSA-N 0.000 claims 1
239000000203 mixture Substances 0.000 claims 1
CYNCLJZSLURWDD-UHFFFAOYSA-N n-(2-chlorophenyl)-1-methyl-5-[2-[5-(trifluoromethyl)-1h-imidazol-2-yl]pyridin-4-yl]oxybenzimidazol-2-amine Chemical compound N=1C2=CC(OC=3C=C(N=CC=3)C=3NC(=CN=3)C(F)(F)F)=CC=C2N(C)C=1NC1=CC=CC=C1Cl CYNCLJZSLURWDD-UHFFFAOYSA-N 0.000 claims 1
NOBWZSLSVIUZAX-UHFFFAOYSA-N n-(2-ethylphenyl)-1-methyl-5-[2-[5-(trifluoromethyl)-1h-imidazol-2-yl]pyridin-4-yl]oxybenzimidazol-2-amine Chemical compound CCC1=CC=CC=C1NC1=NC2=CC(OC=3C=C(N=CC=3)C=3NC(=CN=3)C(F)(F)F)=CC=C2N1C NOBWZSLSVIUZAX-UHFFFAOYSA-N 0.000 claims 1
PWWZOONQYQLJBE-UHFFFAOYSA-N n-(2-hydroxyethyl)-2-[4-[1-methyl-2-[4-(trifluoromethyl)anilino]benzimidazol-5-yl]oxypyridin-2-yl]-1h-imidazole-5-carboxamide Chemical compound N=1C2=CC(OC=3C=C(N=CC=3)C=3NC(=CN=3)C(=O)NCCO)=CC=C2N(C)C=1NC1=CC=C(C(F)(F)F)C=C1 PWWZOONQYQLJBE-UHFFFAOYSA-N 0.000 claims 1
ZEUAXTRKGYORKF-UHFFFAOYSA-N n-(3-ethylphenyl)-1-methyl-5-[2-[5-(trifluoromethyl)-1h-imidazol-2-yl]pyridin-4-yl]oxybenzimidazol-2-amine Chemical compound CCC1=CC=CC(NC=2N(C3=CC=C(OC=4C=C(N=CC=4)C=4NC(=CN=4)C(F)(F)F)C=C3N=2)C)=C1 ZEUAXTRKGYORKF-UHFFFAOYSA-N 0.000 claims 1
FHQUGILIWIXMQJ-UHFFFAOYSA-N n-(4-bromophenyl)-1-methyl-5-[2-[5-(trifluoromethyl)-1h-imidazol-2-yl]pyridin-4-yl]oxybenzimidazol-2-amine Chemical compound N=1C2=CC(OC=3C=C(N=CC=3)C=3NC(=CN=3)C(F)(F)F)=CC=C2N(C)C=1NC1=CC=C(Br)C=C1 FHQUGILIWIXMQJ-UHFFFAOYSA-N 0.000 claims 1
UULHAECZZWRIHA-UHFFFAOYSA-N n-(4-chlorophenyl)-1-methyl-5-[2-[5-(trifluoromethyl)-1h-imidazol-2-yl]pyridin-4-yl]oxybenzimidazol-2-amine Chemical compound N=1C2=CC(OC=3C=C(N=CC=3)C=3NC(=CN=3)C(F)(F)F)=CC=C2N(C)C=1NC1=CC=C(Cl)C=C1 UULHAECZZWRIHA-UHFFFAOYSA-N 0.000 claims 1
UNNIFOKCWPGGRX-UHFFFAOYSA-N n-(4-ethylphenyl)-1-methyl-5-[2-[5-(trifluoromethyl)-1h-imidazol-2-yl]pyridin-4-yl]oxybenzimidazol-2-amine Chemical compound C1=CC(CC)=CC=C1NC1=NC2=CC(OC=3C=C(N=CC=3)C=3NC(=CN=3)C(F)(F)F)=CC=C2N1C UNNIFOKCWPGGRX-UHFFFAOYSA-N 0.000 claims 1
JOJYJDOMFMIRKR-UHFFFAOYSA-N n-(4-tert-butylphenyl)-1-methyl-5-[2-(5-methyl-4-phenyl-1h-imidazol-2-yl)pyridin-4-yl]oxybenzimidazol-2-amine Chemical compound CC=1NC(C=2N=CC=C(OC=3C=C4N=C(NC=5C=CC(=CC=5)C(C)(C)C)N(C)C4=CC=3)C=2)=NC=1C1=CC=CC=C1 JOJYJDOMFMIRKR-UHFFFAOYSA-N 0.000 claims 1
UKHGHPIFGONHOV-UHFFFAOYSA-N n-(4-tert-butylphenyl)-1-methyl-5-[2-[4-phenyl-5-(trifluoromethyl)-1h-imidazol-2-yl]pyridin-4-yl]oxybenzimidazol-2-amine Chemical compound N=1C2=CC(OC=3C=C(N=CC=3)C=3NC(=C(N=3)C=3C=CC=CC=3)C(F)(F)F)=CC=C2N(C)C=1NC1=CC=C(C(C)(C)C)C=C1 UKHGHPIFGONHOV-UHFFFAOYSA-N 0.000 claims 1
GWKBJILKCSXHMY-UHFFFAOYSA-N n-(5-tert-butyl-2-chlorophenyl)-1-methyl-5-[2-[5-(trifluoromethyl)-1h-imidazol-2-yl]pyridin-4-yl]oxybenzimidazol-2-amine Chemical compound N=1C2=CC(OC=3C=C(N=CC=3)C=3NC(=CN=3)C(F)(F)F)=CC=C2N(C)C=1NC1=CC(C(C)(C)C)=CC=C1Cl GWKBJILKCSXHMY-UHFFFAOYSA-N 0.000 claims 1
BCSZFWZJIFOMKQ-UHFFFAOYSA-N n-(5-tert-butyl-2-fluorophenyl)-1-methyl-5-[2-(5-methyl-4-phenyl-1h-imidazol-2-yl)pyridin-4-yl]oxybenzimidazol-2-amine Chemical compound CC=1NC(C=2N=CC=C(OC=3C=C4N=C(NC=5C(=CC=C(C=5)C(C)(C)C)F)N(C)C4=CC=3)C=2)=NC=1C1=CC=CC=C1 BCSZFWZJIFOMKQ-UHFFFAOYSA-N 0.000 claims 1
KLUQUTDAFSUQQQ-UHFFFAOYSA-N n-(5-tert-butyl-2-fluorophenyl)-1-methyl-5-[2-[5-(trifluoromethyl)-1h-imidazol-2-yl]pyridin-4-yl]oxybenzimidazol-2-amine Chemical compound N=1C2=CC(OC=3C=C(N=CC=3)C=3NC(=CN=3)C(F)(F)F)=CC=C2N(C)C=1NC1=CC(C(C)(C)C)=CC=C1F KLUQUTDAFSUQQQ-UHFFFAOYSA-N 0.000 claims 1
LOOGBSGPMZTHIX-UHFFFAOYSA-N n-[2-chloro-4-(trifluoromethyl)phenyl]-1-methyl-5-[2-[5-(trifluoromethyl)-1h-imidazol-2-yl]pyridin-4-yl]oxybenzimidazol-2-amine Chemical compound N=1C2=CC(OC=3C=C(N=CC=3)C=3NC(=CN=3)C(F)(F)F)=CC=C2N(C)C=1NC1=CC=C(C(F)(F)F)C=C1Cl LOOGBSGPMZTHIX-UHFFFAOYSA-N 0.000 claims 1
KBSLJFGAYBKSLV-UHFFFAOYSA-N n-[2-chloro-5-(trifluoromethyl)phenyl]-1-methyl-5-[2-(5-methyl-4-phenyl-1h-imidazol-2-yl)pyridin-4-yl]oxybenzimidazol-2-amine Chemical compound CC=1NC(C=2N=CC=C(OC=3C=C4N=C(NC=5C(=CC=C(C=5)C(F)(F)F)Cl)N(C)C4=CC=3)C=2)=NC=1C1=CC=CC=C1 KBSLJFGAYBKSLV-UHFFFAOYSA-N 0.000 claims 1
QPYNIFPLONQWGU-UHFFFAOYSA-N n-[2-chloro-5-(trifluoromethyl)phenyl]-1-methyl-5-[2-[4-phenyl-5-(trifluoromethyl)-1h-imidazol-2-yl]pyridin-4-yl]oxybenzimidazol-2-amine Chemical compound N=1C2=CC(OC=3C=C(N=CC=3)C=3NC(=C(N=3)C=3C=CC=CC=3)C(F)(F)F)=CC=C2N(C)C=1NC1=CC(C(F)(F)F)=CC=C1Cl QPYNIFPLONQWGU-UHFFFAOYSA-N 0.000 claims 1
PYBSLQNYWLNLKV-UHFFFAOYSA-N n-[2-fluoro-5-(trifluoromethyl)phenyl]-1-methyl-5-[2-(5-methyl-4-phenyl-1h-imidazol-2-yl)pyridin-4-yl]oxybenzimidazol-2-amine Chemical compound CC=1NC(C=2N=CC=C(OC=3C=C4N=C(NC=5C(=CC=C(C=5)C(F)(F)F)F)N(C)C4=CC=3)C=2)=NC=1C1=CC=CC=C1 PYBSLQNYWLNLKV-UHFFFAOYSA-N 0.000 claims 1
OCTPLXRWWSCLMD-UHFFFAOYSA-N n-[2-fluoro-5-(trifluoromethyl)phenyl]-1-methyl-5-[2-[4-phenyl-5-(trifluoromethyl)-1h-imidazol-2-yl]pyridin-4-yl]oxybenzimidazol-2-amine Chemical compound N=1C2=CC(OC=3C=C(N=CC=3)C=3NC(=C(N=3)C=3C=CC=CC=3)C(F)(F)F)=CC=C2N(C)C=1NC1=CC(C(F)(F)F)=CC=C1F OCTPLXRWWSCLMD-UHFFFAOYSA-N 0.000 claims 1
VDWDZORLKMAOGO-UHFFFAOYSA-N n-[2-fluoro-5-(trifluoromethyl)phenyl]-1-methyl-5-[2-[5-methyl-4-[3-(trifluoromethyl)phenyl]-1h-imidazol-2-yl]pyridin-4-yl]oxybenzimidazol-2-amine Chemical compound CC=1NC(C=2N=CC=C(OC=3C=C4N=C(NC=5C(=CC=C(C=5)C(F)(F)F)F)N(C)C4=CC=3)C=2)=NC=1C1=CC=CC(C(F)(F)F)=C1 VDWDZORLKMAOGO-UHFFFAOYSA-N 0.000 claims 1
BUGGWNWJASBPFW-UHFFFAOYSA-N n-[2-fluoro-5-(trifluoromethyl)phenyl]-1-methyl-5-[2-[5-methyl-4-[4-(trifluoromethyl)phenyl]-1h-imidazol-2-yl]pyridin-4-yl]oxybenzimidazol-2-amine Chemical compound CC=1NC(C=2N=CC=C(OC=3C=C4N=C(NC=5C(=CC=C(C=5)C(F)(F)F)F)N(C)C4=CC=3)C=2)=NC=1C1=CC=C(C(F)(F)F)C=C1 BUGGWNWJASBPFW-UHFFFAOYSA-N 0.000 claims 1
XGBGLHMBKUDHSN-UHFFFAOYSA-N n-[2-fluoro-5-(trifluoromethyl)phenyl]-6-methoxy-1-methyl-5-[2-[5-(trifluoromethyl)-1h-imidazol-2-yl]pyridin-4-yl]oxybenzimidazol-2-amine Chemical compound N=1C=2C=C(OC=3C=C(N=CC=3)C=3NC(=CN=3)C(F)(F)F)C(OC)=CC=2N(C)C=1NC1=CC(C(F)(F)F)=CC=C1F XGBGLHMBKUDHSN-UHFFFAOYSA-N 0.000 claims 1
SMPKBRUCIWKACB-UHFFFAOYSA-N n-[4-fluoro-3-(oxolan-3-yl)phenyl]-1-methyl-5-[2-[5-(trifluoromethyl)-1h-imidazol-2-yl]pyridin-4-yl]oxybenzimidazol-2-amine Chemical compound N=1C2=CC(OC=3C=C(N=CC=3)C=3NC(=CN=3)C(F)(F)F)=CC=C2N(C)C=1NC(C=1)=CC=C(F)C=1C1CCOC1 SMPKBRUCIWKACB-UHFFFAOYSA-N 0.000 claims 1
150000007530 organic bases Chemical class 0.000 claims 1
235000015320 potassium carbonate Nutrition 0.000 claims 1
229910000027 potassium carbonate Inorganic materials 0.000 claims 1
235000011118 potassium hydroxide Nutrition 0.000 claims 1
JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical group [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 claims 1
235000011121 sodium hydroxide Nutrition 0.000 claims 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1

Classifications

- 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
- C07D401/14—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 three or more hetero rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- 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
- 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
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Hematology (AREA)
Oncology (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

HR20110312T 2005-08-30 2011-04-29 Supstituirani benzimidazoli i postupci pripreme HRP20110312T1 (hr)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
US71310805P	2005-08-30	2005-08-30
US71253905P	2005-08-30	2005-08-30
US73159105P	2005-10-27	2005-10-27
US77468406P	2006-02-17	2006-02-17
PCT/US2006/034112 WO2007027950A1 (en)	2005-08-30	2006-08-30	Substituted benzimidazoles and methods of preparation

Publications (1)

Publication Number	Publication Date
HRP20110312T1 true HRP20110312T1 (hr)	2011-08-31

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HR20110312T HRP20110312T1 (hr)	2005-08-30	2011-04-29	Supstituirani benzimidazoli i postupci pripreme
HR20110939T HRP20110939T1 (hr)	2005-08-30	2011-12-15	Supstituirani benzimidazoli kao inhibitori kinaze

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HR20110939T HRP20110939T1 (hr)	2005-08-30	2011-12-15	Supstituirani benzimidazoli kao inhibitori kinaze

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US (6)	US7482367B2 (es)
EP (2)	EP1924577B1 (es)
JP (4)	JP5210866B2 (es)
KR (2)	KR20080039965A (es)
AR (2)	AR055622A1 (es)
AT (2)	ATE526325T1 (es)
AU (2)	AU2006284666B2 (es)
BR (2)	BRPI0615309B1 (es)
CA (2)	CA2619966A1 (es)
CR (1)	CR9716A (es)
CU (1)	CU23784B7 (es)
CY (2)	CY1111871T1 (es)
DE (1)	DE602006021036D1 (es)
DK (2)	DK1926722T3 (es)
EA (1)	EA014230B1 (es)
EC (2)	ECSP088210A (es)
ES (1)	ES2374451T3 (es)
GE (1)	GEP20105004B (es)
GT (1)	GT200600394A (es)
HK (2)	HK1117519A1 (es)
HN (1)	HN2008000317A (es)
HR (2)	HRP20110312T1 (es)
IL (2)	IL189080A (es)
MA (2)	MA29915B1 (es)
MY (2)	MY163886A (es)
NI (1)	NI200800060A (es)
NO (1)	NO20081476L (es)
NZ (2)	NZ565450A (es)
PE (2)	PE20070335A1 (es)
PL (2)	PL1926722T3 (es)
PT (2)	PT1926722E (es)
RS (1)	RS52099B (es)
SI (2)	SI1924577T1 (es)
SM (1)	SMAP200800022A (es)
TN (2)	TNSN08089A1 (es)
TW (2)	TWI387592B (es)
WO (2)	WO2007027950A1 (es)

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- 2011-12-15 HR HR20110939T patent/HRP20110939T1/hr unknown
2012
- 2012-12-03 JP JP2012264553A patent/JP2013060458A/ja active Pending
- 2012-12-03 JP JP2012264552A patent/JP2013060457A/ja not_active Withdrawn

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Publication number	Publication date
HN2008000317A (es)	2011-02-16
ATE526325T1 (de)	2011-10-15
MA29915B1 (fr)	2008-11-03
TWI387592B (zh)	2013-03-01
ECSP088210A (es)	2008-03-26
CR9716A (es)	2008-04-16
PL1926722T3 (pl)	2012-02-29
HK1117523A1 (en)	2009-01-16
US7482367B2 (en)	2009-01-27
BRPI0615309B1 (pt)	2021-07-27
ECSP088218A (es)	2008-03-26
EP1926722B1 (en)	2011-09-28
AU2006284666B2 (en)	2011-04-28
JP5210866B2 (ja)	2013-06-12
US20090170904A1 (en)	2009-07-02
CU20080027A7 (es)	2010-12-08
EA014230B1 (ru)	2010-10-29
MY163886A (en)	2017-11-15
SMP200800022B (it)	2008-04-02
SMAP200800022A (it)	2008-04-02
JP2009507026A (ja)	2009-02-19
PT1924577E (pt)	2011-07-04
NI200800060A (es)	2009-03-03
BRPI0615314A2 (pt)	2011-05-17
JP2009507794A (ja)	2009-02-26
EP1926722A1 (en)	2008-06-04
MA29772B1 (fr)	2008-09-01
SI1924577T1 (sl)	2011-07-29
AU2006284666A1 (en)	2007-03-08
CA2620472A1 (en)	2007-03-15
PE20070427A1 (es)	2007-04-21
US7767820B2 (en)	2010-08-03
EP1924577B1 (en)	2011-03-30
SI1926722T1 (sl)	2012-01-31
EP1924577A1 (en)	2008-05-28
ES2374451T3 (es)	2012-02-16
US20080287682A1 (en)	2008-11-20
NZ565450A (en)	2011-04-29
TW200804345A (en)	2008-01-16
RS52099B (en)	2012-06-30
US20100256375A1 (en)	2010-10-07
JP2013060457A (ja)	2013-04-04
US20070049622A1 (en)	2007-03-01
AR055622A1 (es)	2007-08-29
AU2006287688A1 (en)	2007-03-15
KR20080039964A (ko)	2008-05-07
WO2007027950A1 (en)	2007-03-08
HRP20110939T1 (hr)	2012-01-31
DK1926722T3 (da)	2011-12-19
JP5210867B2 (ja)	2013-06-12
NO20081476L (no)	2008-03-26
ATE503751T1 (de)	2011-04-15
BRPI0615309A2 (pt)	2011-05-17
MY148694A (en)	2013-05-31
JP2013060458A (ja)	2013-04-04
IL189080A0 (en)	2008-08-07
TNSN08088A1 (en)	2009-07-14
US8592459B2 (en)	2013-11-26
CU23784B7 (es)	2012-02-15
TW200804346A (en)	2008-01-16
CA2620472C (en)	2013-12-24
CA2619966A1 (en)	2007-03-08
WO2007030377A1 (en)	2007-03-15
TNSN08089A1 (en)	2009-07-14
IL189080A (en)	2013-05-30
US20070161680A1 (en)	2007-07-12
DK1924577T3 (da)	2011-05-16
AR057109A1 (es)	2007-11-14
GEP20105004B (en)	2010-06-10
CY1112157T1 (el)	2015-12-09
PL1924577T3 (pl)	2011-09-30
IL189194A0 (en)	2008-06-05
GT200600394A (es)	2008-03-17
EA200800441A1 (ru)	2008-08-29
CY1111871T1 (el)	2015-11-04
NZ565451A (en)	2011-05-27
PE20070335A1 (es)	2007-04-21
IL189194A (en)	2013-09-30
US20100234394A1 (en)	2010-09-16
DE602006021036D1 (de)	2011-05-12
AU2006287688B2 (en)	2010-08-19
KR20080039965A (ko)	2008-05-07
PT1926722E (pt)	2012-01-11
US7732465B2 (en)	2010-06-08
HK1117519A1 (en)	2009-01-16

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