SK286773B6 - Benzoimidazolové zlúčeniny, ich použitie a farmaceutické kompozície s ich obsahom - Google Patents

Benzoimidazolové zlúčeniny, ich použitie a farmaceutické kompozície s ich obsahom Download PDF

Info

Publication number: SK286773B6
Authority: SK; Slovakia
Prior art keywords: quinolin; benzoimidazol; piperidin; methoxy; ethoxy
Prior art date: 1999-11-30

Application number

SK717-2002A

Other languages

English (en)

Slovak (sk)

Other versions

SK7172002A3 (en

Inventor

Wayne Ernest Barth

Michael Joseph Luzzio

Joseph Peter Lyssikatos

Original Assignee

Pfizer Products Inc.

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.)

1999-11-30

Filing date

2000-11-10

Publication date

2009-05-07

2000-11-10 Application filed by Pfizer Products Inc. filed Critical Pfizer Products Inc.

2004-07-07 Publication of SK7172002A3 publication Critical patent/SK7172002A3/sk

2009-05-07 Publication of SK286773B6 publication Critical patent/SK286773B6/sk

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 377
239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 21
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical class C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 title abstract description 3
150000003839 salts Chemical class 0.000 claims abstract description 66
229940002612 prodrug Drugs 0.000 claims abstract description 48
239000000651 prodrug Substances 0.000 claims abstract description 48
239000012453 solvate Substances 0.000 claims abstract description 28
241000124008 Mammalia Species 0.000 claims abstract description 27
206010028980 Neoplasm Diseases 0.000 claims abstract description 22
230000002159 abnormal effect Effects 0.000 claims abstract description 19
230000010261 cell growth Effects 0.000 claims abstract description 17
201000011510 cancer Diseases 0.000 claims abstract description 15
239000003814 drug Substances 0.000 claims abstract description 5
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 287
-1 benzoimidazole compound Chemical class 0.000 claims description 213
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 125
BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 64
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 62
125000000217 alkyl group Chemical group 0.000 claims description 54
125000003118 aryl group Chemical group 0.000 claims description 41
125000000623 heterocyclic group Chemical group 0.000 claims description 41
229910052757 nitrogen Inorganic materials 0.000 claims description 40
125000004432 carbon atom Chemical group C* 0.000 claims description 38
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 25
125000000753 cycloalkyl group Chemical group 0.000 claims description 25
125000004043 oxo group Chemical group O=* 0.000 claims description 24
125000001424 substituent group Chemical group 0.000 claims description 21
239000001257 hydrogen Substances 0.000 claims description 20
229910052739 hydrogen Inorganic materials 0.000 claims description 20
125000004093 cyano group Chemical group *C#N 0.000 claims description 17
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 17
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 17
229910052736 halogen Inorganic materials 0.000 claims description 15
150000002367 halogens Chemical class 0.000 claims description 15
229910052717 sulfur Inorganic materials 0.000 claims description 15
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
125000004430 oxygen atom Chemical group O* 0.000 claims description 14
125000004434 sulfur atom Chemical group 0.000 claims description 14
229910052799 carbon Inorganic materials 0.000 claims description 13
BCRKZBOQBMOOKE-UHFFFAOYSA-N 1-[2-(5-methoxybenzimidazol-1-yl)quinolin-8-yl]piperidin-4-amine Chemical compound C1=NC2=CC(OC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CCC(N)CC1 BCRKZBOQBMOOKE-UHFFFAOYSA-N 0.000 claims description 12
BVEMGSLZVMDRAU-UHFFFAOYSA-N 2-[5-(2-methoxyethoxy)benzimidazol-1-yl]-8-piperazin-1-ylquinoline Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CCNCC1 BVEMGSLZVMDRAU-UHFFFAOYSA-N 0.000 claims description 11
UHFSUALOJAJWEA-UHFFFAOYSA-N 4-[(dimethylamino)methyl]-1-[2-(5-methoxybenzimidazol-1-yl)quinolin-8-yl]piperidin-4-ol Chemical compound C1=NC2=CC(OC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CCC(O)(CN(C)C)CC1 UHFSUALOJAJWEA-UHFFFAOYSA-N 0.000 claims description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
GQQCLFHJSQYYRZ-SFHVURJKSA-N (2s)-2-amino-1-[4-[2-[5-(2-methoxyethoxy)benzimidazol-1-yl]quinolin-8-yl]piperazin-1-yl]propan-1-one Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CCN(C(=O)[C@H](C)N)CC1 GQQCLFHJSQYYRZ-SFHVURJKSA-N 0.000 claims description 9
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 9
125000000304 alkynyl group Chemical group 0.000 claims description 9
IDCRQLNHZFWXQL-VSGBNLITSA-N (3r,4r)-1-[[4-[2-[5-(2-methoxyethoxy)benzimidazol-1-yl]quinolin-8-yl]phenyl]methyl]pyrrolidine-3,4-diol Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2C(C=C1)=CC=C1CN1C[C@@H](O)[C@H](O)C1 IDCRQLNHZFWXQL-VSGBNLITSA-N 0.000 claims description 8
YNGYWZGVAHWYKA-UHFFFAOYSA-N 2-[5-(2-methoxyethoxy)benzimidazol-1-yl]-8-[4-(pyrrolidin-1-ylmethyl)phenyl]quinoline Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2C(C=C1)=CC=C1CN1CCCC1 YNGYWZGVAHWYKA-UHFFFAOYSA-N 0.000 claims description 8
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
239000001301 oxygen Substances 0.000 claims description 8
229910052760 oxygen Inorganic materials 0.000 claims description 8
VPRSVWZVGUUJIY-UHFFFAOYSA-N piperidin-4-amine trihydrochloride Chemical compound Cl.Cl.Cl.N1CCC(CC1)N VPRSVWZVGUUJIY-UHFFFAOYSA-N 0.000 claims description 8
125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 claims description 8
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 7
125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 7
239000003937 drug carrier Substances 0.000 claims description 7
JMRIHUUTAOOKNK-UHFFFAOYSA-N 4-[2-[5-(2-methoxyethoxy)benzimidazol-1-yl]quinolin-8-yl]phenol Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2C1=CC=C(O)C=C1 JMRIHUUTAOOKNK-UHFFFAOYSA-N 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 6
150000002431 hydrogen Chemical class 0.000 claims description 6
RMKKMPKSAYASLE-UHFFFAOYSA-N methyl 2-(5-methoxybenzimidazol-1-yl)quinoline-8-carboxylate Chemical compound C1=NC2=CC(OC)=CC=C2N1C1=CC=C2C=CC=C(C(=O)OC)C2=N1 RMKKMPKSAYASLE-UHFFFAOYSA-N 0.000 claims description 6
QSADGXBBPXYCDY-UHFFFAOYSA-N methyl 2-[5-(cyclopropylmethoxy)benzimidazol-1-yl]quinoline-8-carboxylate Chemical compound N1=C2C(C(=O)OC)=CC=CC2=CC=C1N(C1=CC=2)C=NC1=CC=2OCC1CC1 QSADGXBBPXYCDY-UHFFFAOYSA-N 0.000 claims description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 5
RZIWPOGNSBXHPA-UHFFFAOYSA-N 1-[4-[2-(5-methoxybenzimidazol-1-yl)quinolin-8-yl]phenyl]-n-methylmethanamine Chemical compound C1=CC(CNC)=CC=C1C1=CC=CC2=CC=C(N3C4=CC=C(OC)C=C4N=C3)N=C12 RZIWPOGNSBXHPA-UHFFFAOYSA-N 0.000 claims description 5
QBUAJCWWXANPTG-UHFFFAOYSA-N 1-[4-[2-[5-(2-methoxyethoxy)benzimidazol-1-yl]quinolin-8-yl]phenyl]-n,n-dimethylmethanamine Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2C1=CC=C(CN(C)C)C=C1 QBUAJCWWXANPTG-UHFFFAOYSA-N 0.000 claims description 5
PZEKBYFAUUSSQG-UHFFFAOYSA-N 1-[4-[2-[5-(2-methoxyethoxy)benzimidazol-1-yl]quinolin-8-yl]phenyl]-n-methylmethanamine Chemical compound C1=CC(CNC)=CC=C1C1=CC=CC2=CC=C(N3C4=CC=C(OCCOC)C=C4N=C3)N=C12 PZEKBYFAUUSSQG-UHFFFAOYSA-N 0.000 claims description 5
RUPVQNDWKLBVDU-UHFFFAOYSA-N 1-[[4-[2-[5-(2-methoxyethoxy)benzimidazol-1-yl]quinolin-8-yl]phenyl]methyl]pyrrolidin-3-ol Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2C(C=C1)=CC=C1CN1CCC(O)C1 RUPVQNDWKLBVDU-UHFFFAOYSA-N 0.000 claims description 5
DGHZZUOQUBRWOY-UHFFFAOYSA-N 2-[4-[2-[5-(2-methoxyethoxy)benzimidazol-1-yl]quinolin-8-yl]phenoxy]-n,n-dimethylethanamine Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2C1=CC=C(OCCN(C)C)C=C1 DGHZZUOQUBRWOY-UHFFFAOYSA-N 0.000 claims description 5
OCHFZSPSLJYOMM-UHFFFAOYSA-N 2-[4-[2-[5-(2-methoxyethoxy)benzimidazol-1-yl]quinolin-8-yl]piperazin-1-yl]-n,n-dimethylethanamine Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CCN(CCN(C)C)CC1 OCHFZSPSLJYOMM-UHFFFAOYSA-N 0.000 claims description 5
UQAFKTILPAHTJV-UHFFFAOYSA-N 2-[4-[2-[5-(2-methoxyethoxy)benzimidazol-1-yl]quinolin-8-yl]piperazin-1-yl]ethanamine Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CCN(CCN)CC1 UQAFKTILPAHTJV-UHFFFAOYSA-N 0.000 claims description 5
XNRNUEVAHHSIDN-UHFFFAOYSA-N 2-[[4-[2-[5-(2-methoxyethoxy)benzimidazol-1-yl]quinolin-8-yl]phenyl]methylamino]ethanol Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2C1=CC=C(CNCCO)C=C1 XNRNUEVAHHSIDN-UHFFFAOYSA-N 0.000 claims description 5
JLVDWXVHUOAPQZ-UHFFFAOYSA-N 4-(aminomethyl)-1-[2-(5-methoxybenzimidazol-1-yl)quinolin-8-yl]piperidin-4-ol Chemical compound C1=NC2=CC(OC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CCC(O)(CN)CC1 JLVDWXVHUOAPQZ-UHFFFAOYSA-N 0.000 claims description 5
125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 4
DWNNTUUIPKZWOZ-UHFFFAOYSA-N 1-[1-[2-[5-(2-methoxyethoxy)benzimidazol-1-yl]quinolin-8-yl]piperidin-4-yl]-n,n-dimethylmethanamine Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CCC(CN(C)C)CC1 DWNNTUUIPKZWOZ-UHFFFAOYSA-N 0.000 claims description 4
AGWUMAILSPVGAK-UHFFFAOYSA-N 1-[2-(6,7-dihydro-[1,4]dioxino[2,3-f]benzimidazol-3-yl)quinolin-8-yl]piperidin-4-amine Chemical compound C1CC(N)CCN1C1=CC=CC2=CC=C(N3C4=CC=5OCCOC=5C=C4N=C3)N=C12 AGWUMAILSPVGAK-UHFFFAOYSA-N 0.000 claims description 4
MSEZXYYREBXKOC-UHFFFAOYSA-N 1-[2-[5-(cyclopropylmethoxy)benzimidazol-1-yl]quinolin-8-yl]-n-methylpiperidin-4-amine Chemical compound C1CC(NC)CCN1C1=CC=CC2=CC=C(N3C4=CC=C(OCC5CC5)C=C4N=C3)N=C12 MSEZXYYREBXKOC-UHFFFAOYSA-N 0.000 claims description 4
OMYHHUQIMSIHMC-UHFFFAOYSA-N 1-[2-[5-[2-(1,2,4-triazol-1-yl)ethoxy]benzimidazol-1-yl]quinolin-8-yl]piperidin-4-amine Chemical compound C1CC(N)CCN1C1=CC=CC2=CC=C(N3C4=CC=C(OCCN5N=CN=C5)C=C4N=C3)N=C12 OMYHHUQIMSIHMC-UHFFFAOYSA-N 0.000 claims description 4
IJZNZDAHGOCSOM-UHFFFAOYSA-N 1-[2-[5-[4-(aminomethyl)phenyl]benzimidazol-1-yl]quinolin-8-yl]piperidin-4-amine Chemical compound C1=CC(CN)=CC=C1C1=CC=C(N(C=N2)C=3N=C4C(N5CCC(N)CC5)=CC=CC4=CC=3)C2=C1 IJZNZDAHGOCSOM-UHFFFAOYSA-N 0.000 claims description 4
ZBVXRRVOZXKWDG-UHFFFAOYSA-N 1-[4-[2-(5-methoxybenzimidazol-1-yl)quinolin-8-yl]phenyl]-n,n-dimethylmethanamine Chemical compound C1=NC2=CC(OC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2C1=CC=C(CN(C)C)C=C1 ZBVXRRVOZXKWDG-UHFFFAOYSA-N 0.000 claims description 4
DSGDSGYKHRAECH-UHFFFAOYSA-N 1-[[4-[2-[5-(2-methoxyethoxy)benzimidazol-1-yl]quinolin-8-yl]phenyl]methyl]azetidin-3-ol Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2C(C=C1)=CC=C1CN1CC(O)C1 DSGDSGYKHRAECH-UHFFFAOYSA-N 0.000 claims description 4
DXIXTMZBBLHIPV-UHFFFAOYSA-N 2-(dimethylamino)-1-[4-[2-[5-(2-methoxyethoxy)benzimidazol-1-yl]quinolin-8-yl]piperazin-1-yl]ethanone Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CCN(C(=O)CN(C)C)CC1 DXIXTMZBBLHIPV-UHFFFAOYSA-N 0.000 claims description 4
HRAONBDRSKGMTJ-UHFFFAOYSA-N 2-[1-[8-(4-aminopiperidin-1-yl)quinolin-2-yl]benzimidazol-5-yl]oxyethanol Chemical compound C1CC(N)CCN1C1=CC=CC2=CC=C(N3C4=CC=C(OCCO)C=C4N=C3)N=C12 HRAONBDRSKGMTJ-UHFFFAOYSA-N 0.000 claims description 4
DCXUGMGXTCRQOT-UHFFFAOYSA-N 2-[2-(5-methoxybenzimidazol-1-yl)quinolin-8-yl]oxy-n-methylethanamine Chemical compound C1=NC2=CC(OC)=CC=C2N1C1=CC=C2C=CC=C(OCCNC)C2=N1 DCXUGMGXTCRQOT-UHFFFAOYSA-N 0.000 claims description 4
IPQOOCCHFQUYCF-UHFFFAOYSA-N 2-[5-(2-methoxyethoxy)benzimidazol-1-yl]-8-[4-[(4-methylpiperazin-1-yl)methyl]piperidin-1-yl]quinoline Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N(CC1)CCC1CN1CCN(C)CC1 IPQOOCCHFQUYCF-UHFFFAOYSA-N 0.000 claims description 4
XUSIOSUAVDIBLY-UHFFFAOYSA-N 4-[1-[8-(4-aminopiperidin-1-yl)quinolin-2-yl]benzimidazol-5-yl]phenol Chemical compound C1CC(N)CCN1C1=CC=CC2=CC=C(N3C4=CC=C(C=C4N=C3)C=3C=CC(O)=CC=3)N=C12 XUSIOSUAVDIBLY-UHFFFAOYSA-N 0.000 claims description 4
DGPYFHFGRRKDPF-UHFFFAOYSA-N 4-[2-[6-(3-aminopropoxy)-1H-benzimidazol-2-yl]quinolin-8-yl]phenol Chemical compound NCCCOc1ccc2[nH]c(nc2c1)-c1ccc2cccc(-c3ccc(O)cc3)c2n1 DGPYFHFGRRKDPF-UHFFFAOYSA-N 0.000 claims description 4
208000026310 Breast neoplasm Diseases 0.000 claims description 4
125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 4
208000024770 Thyroid neoplasm Diseases 0.000 claims description 4
206010046392 Ureteric cancer Diseases 0.000 claims description 4
DRFRUPZYYYSKIE-UHFFFAOYSA-N [4-[2-[5-(2-methoxyethoxy)benzimidazol-1-yl]quinolin-8-yl]phenyl]methanamine Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2C1=CC=C(CN)C=C1 DRFRUPZYYYSKIE-UHFFFAOYSA-N 0.000 claims description 4
239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 4
YZOPDAYZWKIZOB-UHFFFAOYSA-N ethyl 1-[2-(5-methoxybenzimidazol-1-yl)quinolin-8-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=CC=CC2=CC=C(N3C4=CC=C(OC)C=C4N=C3)N=C12 YZOPDAYZWKIZOB-UHFFFAOYSA-N 0.000 claims description 4
WJDANXXQVVQSRR-UHFFFAOYSA-N ethyl 1-[8-(4-aminopiperidin-1-yl)quinolin-2-yl]benzimidazole-5-carboxylate Chemical compound C1=NC2=CC(C(=O)OCC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CCC(N)CC1 WJDANXXQVVQSRR-UHFFFAOYSA-N 0.000 claims description 4
210000003734 kidney Anatomy 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
201000001441 melanoma Diseases 0.000 claims description 4
TWMZLIFUZDBUOD-UHFFFAOYSA-N methyl 4-[1-[8-(4-aminopiperidin-1-yl)quinolin-2-yl]benzimidazol-5-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=C(N(C=N2)C=3N=C4C(N5CCC(N)CC5)=CC=CC4=CC=3)C2=C1 TWMZLIFUZDBUOD-UHFFFAOYSA-N 0.000 claims description 4
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
CXYAHOKJYLLYJG-HXUWFJFHSA-N (2r)-2-amino-3-[4-[2-[5-(2-methoxyethoxy)benzimidazol-1-yl]quinolin-8-yl]piperazin-1-yl]propan-1-ol Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CCN(C[C@@H](N)CO)CC1 CXYAHOKJYLLYJG-HXUWFJFHSA-N 0.000 claims description 3
BHFNNIGVTSAIGD-KRWDZBQOSA-N (3s)-1-[2-[5-(2-methoxyethoxy)benzimidazol-1-yl]quinolin-8-yl]pyrrolidin-3-amine Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CC[C@H](N)C1 BHFNNIGVTSAIGD-KRWDZBQOSA-N 0.000 claims description 3
DSOPCJDOYLTEAH-UHFFFAOYSA-N 1-[1-[2-[5-(2-methoxyethoxy)benzimidazol-1-yl]quinolin-8-yl]piperidin-4-yl]-n-methylmethanamine Chemical compound C1CC(CNC)CCN1C1=CC=CC2=CC=C(N3C4=CC=C(OCCOC)C=C4N=C3)N=C12 DSOPCJDOYLTEAH-UHFFFAOYSA-N 0.000 claims description 3
AWXYFYFBKOXFSQ-UHFFFAOYSA-N 1-[2-(5-ethoxybenzimidazol-1-yl)quinolin-8-yl]-n,n-dimethylpiperidin-4-amine Chemical compound C1=NC2=CC(OCC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CCC(N(C)C)CC1 AWXYFYFBKOXFSQ-UHFFFAOYSA-N 0.000 claims description 3
BOSNLMMFMCANGE-UHFFFAOYSA-N 1-[2-(5-methoxybenzimidazol-1-yl)quinolin-8-yl]piperidine-4-carboxylic acid Chemical compound C1=NC2=CC(OC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CCC(C(O)=O)CC1 BOSNLMMFMCANGE-UHFFFAOYSA-N 0.000 claims description 3
FPNNXTVDMZIKFS-UHFFFAOYSA-N 1-[2-[5-(pyridin-2-ylmethoxy)benzimidazol-1-yl]quinolin-8-yl]piperidin-4-amine Chemical compound C1CC(N)CCN1C1=CC=CC2=CC=C(N3C4=CC=C(OCC=5N=CC=CC=5)C=C4N=C3)N=C12 FPNNXTVDMZIKFS-UHFFFAOYSA-N 0.000 claims description 3
DHPBYLNWEUHIIO-UHFFFAOYSA-N 1-[2-[5-[2-(2-methylimidazol-1-yl)ethoxy]benzimidazol-1-yl]quinolin-8-yl]piperidin-4-amine Chemical compound CC1=NC=CN1CCOC1=CC=C(N(C=N2)C=3N=C4C(N5CCC(N)CC5)=CC=CC4=CC=3)C2=C1 DHPBYLNWEUHIIO-UHFFFAOYSA-N 0.000 claims description 3
QEKDOMNEJOSDAR-UHFFFAOYSA-N 1-[4-[2-(5-ethoxybenzimidazol-1-yl)quinolin-8-yl]phenyl]-n,n-dimethylmethanamine Chemical compound C1=NC2=CC(OCC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2C1=CC=C(CN(C)C)C=C1 QEKDOMNEJOSDAR-UHFFFAOYSA-N 0.000 claims description 3
FVPLCUUKDHOPEN-UHFFFAOYSA-N 1-[[1-[2-[5-(2-methoxyethoxy)benzimidazol-1-yl]quinolin-8-yl]piperidin-4-yl]amino]-2-methylpropan-2-ol Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CCC(NCC(C)(C)O)CC1 FVPLCUUKDHOPEN-UHFFFAOYSA-N 0.000 claims description 3
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Classifications

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- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
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SK717-2002A 1999-11-30 2000-11-10 Benzoimidazolové zlúčeniny, ich použitie a farmaceutické kompozície s ich obsahom SK286773B6 (sk)

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Application Number	Priority Date	Filing Date	Title
US16821799P	1999-11-30	1999-11-30
PCT/IB2000/001636 WO2001040217A1 (fr)	1999-11-30	2000-11-10	Nouveaux derives benzoimidazole convenant comme agents antiproliferatifs

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SK7172002A3 SK7172002A3 (en)	2004-07-07
SK286773B6 true SK286773B6 (sk)	2009-05-07

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US (1)	US7019147B1 (fr)
EP (1)	EP1235825B1 (fr)
JP (2)	JP4522635B2 (fr)
KR (1)	KR100479401B1 (fr)
CN (2)	CN101289442A (fr)
AP (1)	AP1895A (fr)
AR (1)	AR026633A1 (fr)
AT (1)	ATE316528T1 (fr)
AU (1)	AU782077B2 (fr)
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BR (1)	BR0015911A (fr)
CA (1)	CA2392973C (fr)
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CR (1)	CR6643A (fr)
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EG (1)	EG24433A (fr)
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GE (1)	GEP20033141B (fr)
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UA (1)	UA75055C2 (fr)
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AU1048001A (en)	2001-06-12
AP2002002529A0 (en)	2002-06-30
MA26847A1 (fr)	2004-12-20
DE60025747T2 (de)	2006-08-31
CZ20021759A3 (cs)	2003-06-18
JP2003515603A (ja)	2003-05-07
YU30702A (sh)	2005-06-10
IS2209B (is)	2007-02-15
ZA200204244B (en)	2003-05-28
HRP20020475B1 (en)	2007-06-30
BG106812A (bg)	2003-01-31
DZ3327A1 (fr)	2001-06-07
SV2002000232A (es)	2002-06-07
NO20022556L (no)	2002-07-29
CA2392973C (fr)	2007-05-15
TNSN00228A1 (fr)	2005-11-10
HU230829B1 (en)	2018-08-28
EG24433A (en)	2009-06-25
EP1235825B1 (fr)	2006-01-25
EA200200509A1 (ru)	2002-10-31
DK1235825T3 (da)	2006-05-15
IL149841A (en)	2008-07-08
GEP20033141B (en)	2003-12-25
EP1235825A1 (fr)	2002-09-04
BR0015911A (pt)	2002-08-06
CA2392973A1 (fr)	2001-06-07
JP2007126468A (ja)	2007-05-24
PE20010899A1 (es)	2001-09-05
HUP0203725A2 (hu)	2003-02-28
NZ518280A (en)	2004-05-28
EE200200276A (et)	2003-06-16
GT200000198A (es)	2002-05-23
KR100479401B1 (ko)	2005-03-28
SK7172002A3 (en)	2004-07-07
PL201784B1 (pl)	2009-05-29
MY128765A (en)	2007-02-28
NO324043B1 (no)	2007-07-30
CZ300789B6 (cs)	2009-08-12
BG65862B1 (bg)	2010-03-31
CO5251455A1 (es)	2003-02-28
ATE316528T1 (de)	2006-02-15
MXPA02005343A (es)	2002-12-11
UA75055C2 (uk)	2006-03-15
HUP0203725A3 (en)	2004-05-28
AU782077B2 (en)	2005-06-30
CR6643A (es)	2003-11-07
WO2001040217A1 (fr)	2001-06-07
RS50800B (sr)	2010-08-31
HRP20020475A2 (en)	2005-10-31
TR200201430T2 (tr)	2003-01-21
NO20022556D0 (no)	2002-05-29
DE60025747D1 (de)	2006-04-13
PL355917A1 (en)	2004-05-31
SI1235825T1 (sl)	2006-06-30
AP1895A (en)	2008-10-08
EE05350B1 (et)	2010-10-15
IL149841A0 (en)	2002-11-10
EA005407B1 (ru)	2005-02-24
AR026633A1 (es)	2003-02-19
KR20020059827A (ko)	2002-07-13
TWI258475B (en)	2006-07-21
IS6341A (is)	2002-04-12
CN101289442A (zh)	2008-10-22
US7019147B1 (en)	2006-03-28
CN1402721A (zh)	2003-03-12
CU23132A3 (es)	2006-05-22
JP4522635B2 (ja)	2010-08-11
PA8507601A1 (es)	2003-02-14
ES2256052T3 (es)	2006-07-16

Publication	Publication Date	Title
SK286773B6 (sk)	2009-05-07	Benzoimidazolové zlúčeniny, ich použitie a farmaceutické kompozície s ich obsahom
EP1594858B1 (fr)	2009-10-14	NOUVEAUX DéRIVéES DE BENZOIMIDAZOLE UTILISéS EN TANT QU'AGENTS ANTIPROLIFéRATIFS
HK1124838A (en)	2009-07-24	Novel benzoimidazole derivatives useful as antiproliferative agents
OA12098A (en)	2006-05-04	Novel benzuoimidazole derivatives useful as antiproliferative agents.
ZA200501353B (en)	2006-09-27	Novel benzoimidazole derivatives useful as antiproliferative agents

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