NO324043B1 - Nye benzoimidazolderivater nyttige som antiproliferative midler, samt anvendelse derav. - Google Patents

Nye benzoimidazolderivater nyttige som antiproliferative midler, samt anvendelse derav. Download PDF

Info

Publication number: NO324043B1
Authority: NO; Norway
Prior art keywords: benzoimidazol; quinolin; methoxy; piperidin; ethoxy
Prior art date: 1999-11-30

Application number

NO20022556A

Other languages

English (en)

Norwegian (no)

Other versions

NO20022556L (no

NO20022556D0 (no

Inventor

Wayne Ernest Barth

Michael Joseph Luzzio

Joseph Peter Lyssikatos

Original Assignee

Pfizer Prod 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

2002-05-29

Publication date

2007-07-30

2002-05-29 Application filed by Pfizer Prod Inc filed Critical Pfizer Prod Inc

2002-05-29 Publication of NO20022556D0 publication Critical patent/NO20022556D0/no

2002-07-29 Publication of NO20022556L publication Critical patent/NO20022556L/no

2007-07-30 Publication of NO324043B1 publication Critical patent/NO324043B1/no

Links

230000001028 anti-proliverative effect Effects 0.000 title description 4
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical class C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 347
-1 C3-G10 cycloalkyl Chemical group 0.000 claims description 69
125000000623 heterocyclic group Chemical group 0.000 claims description 44
150000003839 salts Chemical class 0.000 claims description 36
125000000217 alkyl group Chemical group 0.000 claims description 33
125000000753 cycloalkyl group Chemical group 0.000 claims description 27
206010028980 Neoplasm Diseases 0.000 claims description 19
125000003118 aryl group Chemical group 0.000 claims description 19
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 17
125000004434 sulfur atom Chemical group 0.000 claims description 17
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 16
125000004043 oxo group Chemical group O=* 0.000 claims description 16
125000004430 oxygen atom Chemical group O* 0.000 claims description 16
125000001424 substituent group Chemical group 0.000 claims description 16
DEEOXSOLTLIWMG-UHFFFAOYSA-N 1-[2-[5-(2-methoxyethoxy)-1-benzimidazolyl]-8-quinolinyl]-4-piperidinamine Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CCC(N)CC1 DEEOXSOLTLIWMG-UHFFFAOYSA-N 0.000 claims description 15
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 15
230000002159 abnormal effect Effects 0.000 claims description 15
229910052760 oxygen Inorganic materials 0.000 claims description 15
230000010261 cell growth Effects 0.000 claims description 14
229910052736 halogen Inorganic materials 0.000 claims description 14
150000002367 halogens Chemical class 0.000 claims description 14
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 14
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 13
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 13
125000004093 cyano group Chemical group *C#N 0.000 claims description 13
229910052757 nitrogen Inorganic materials 0.000 claims description 13
239000002253 acid Substances 0.000 claims description 12
201000011510 cancer Diseases 0.000 claims description 12
125000000041 C6-C10 aryl group Chemical group 0.000 claims description 11
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 10
239000012453 solvate Substances 0.000 claims description 10
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 9
125000004429 atom Chemical group 0.000 claims description 9
125000004122 cyclic group Chemical group 0.000 claims description 9
125000005842 heteroatom Chemical group 0.000 claims description 9
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
239000000825 pharmaceutical preparation Substances 0.000 claims description 8
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 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 7
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
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 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
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 6
JJBQCMXPAWDJTC-UHFFFAOYSA-N 1-[2-[5-(2-methoxyethoxy)benzimidazol-1-yl]quinolin-8-yl]-4-methylpiperidin-4-amine Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CCC(C)(N)CC1 JJBQCMXPAWDJTC-UHFFFAOYSA-N 0.000 claims description 6
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 6
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 6
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 6
JMPFBJJAPZNSIH-UHFFFAOYSA-N 1-[8-(4-aminopiperidin-1-yl)quinolin-2-yl]benzimidazol-5-ol Chemical compound C1CC(N)CCN1C1=CC=CC2=CC=C(N3C4=CC=C(O)C=C4N=C3)N=C12 JMPFBJJAPZNSIH-UHFFFAOYSA-N 0.000 claims description 6
WOQQQSUPCAHCFH-UHFFFAOYSA-N 4-(aminomethyl)-1-[2-[5-(pyridin-2-ylmethoxy)benzimidazol-1-yl]quinolin-8-yl]piperidin-4-ol Chemical compound C1CC(CN)(O)CCN1C1=CC=CC2=CC=C(N3C4=CC=C(OCC=5N=CC=CC=5)C=C4N=C3)N=C12 WOQQQSUPCAHCFH-UHFFFAOYSA-N 0.000 claims description 6
UXJGHQQHEIIFAO-UHFFFAOYSA-N [1-[2-[5-(2-methoxyethoxy)benzimidazol-1-yl]quinolin-8-yl]piperidin-4-yl]methanol Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CCC(CO)CC1 UXJGHQQHEIIFAO-UHFFFAOYSA-N 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 6
125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 6
229910052799 carbon Inorganic materials 0.000 claims description 6
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 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
229940080818 propionamide Drugs 0.000 claims description 6
IDCRQLNHZFWXQL-HNRBIFIRSA-N (3s,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-HNRBIFIRSA-N 0.000 claims description 5
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 5
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 5
JNKNUAUYOLHBEI-UHFFFAOYSA-N 1-[2-(5,6-dimethoxybenzimidazol-1-yl)quinolin-8-yl]piperidin-4-amine Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1C(N=C12)=CC=C1C=CC=C2N1CCC(N)CC1 JNKNUAUYOLHBEI-UHFFFAOYSA-N 0.000 claims description 5
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 5
YCYUUTPEQGVZNM-UHFFFAOYSA-N 1-[2-(5-ethoxybenzimidazol-1-yl)quinolin-8-yl]piperidin-4-one Chemical compound C1=NC2=CC(OCC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CCC(=O)CC1 YCYUUTPEQGVZNM-UHFFFAOYSA-N 0.000 claims description 5
MMYDEBFLRLVECR-UHFFFAOYSA-N 1-[2-(5-methoxybenzimidazol-1-yl)quinolin-8-yl]-n,n-dimethylpiperidin-4-amine Chemical compound C1=NC2=CC(OC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CCC(N(C)C)CC1 MMYDEBFLRLVECR-UHFFFAOYSA-N 0.000 claims description 5
ACGUZOBLJIIJSZ-UHFFFAOYSA-N 1-[2-(5-methoxybenzimidazol-1-yl)quinolin-8-yl]piperidin-4-one Chemical compound C1=NC2=CC(OC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CCC(=O)CC1 ACGUZOBLJIIJSZ-UHFFFAOYSA-N 0.000 claims description 5
ZJMUYOGWSXPZEC-UHFFFAOYSA-N 1-[2-(5-phenylbenzimidazol-1-yl)quinolin-8-yl]piperidin-4-amine Chemical compound C1CC(N)CCN1C1=CC=CC2=CC=C(N3C4=CC=C(C=C4N=C3)C=3C=CC=CC=3)N=C12 ZJMUYOGWSXPZEC-UHFFFAOYSA-N 0.000 claims description 5
SNEYBGMVJOEFBD-UHFFFAOYSA-N 1-[2-(5-phenylmethoxybenzimidazol-1-yl)quinolin-8-yl]piperidin-4-amine Chemical compound C1CC(N)CCN1C1=CC=CC2=CC=C(N3C4=CC=C(OCC=5C=CC=CC=5)C=C4N=C3)N=C12 SNEYBGMVJOEFBD-UHFFFAOYSA-N 0.000 claims description 5
QPTCRSKAQPYXRX-UHFFFAOYSA-N 1-[2-(5-pyridin-4-ylbenzimidazol-1-yl)quinolin-8-yl]piperidin-4-amine Chemical compound C1CC(N)CCN1C1=CC=CC2=CC=C(N3C4=CC=C(C=C4N=C3)C=3C=CN=CC=3)N=C12 QPTCRSKAQPYXRX-UHFFFAOYSA-N 0.000 claims description 5
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 5
DCDHJAACRLXPAF-UHFFFAOYSA-N 1-[2-[5-(cyclopropylmethoxy)benzimidazol-1-yl]quinolin-8-yl]-n,n-dimethylpiperidin-4-amine Chemical compound C1CC(N(C)C)CCN1C1=CC=CC2=CC=C(N3C4=CC=C(OCC5CC5)C=C4N=C3)N=C12 DCDHJAACRLXPAF-UHFFFAOYSA-N 0.000 claims description 5
GJHVPIXOGJZNNP-UHFFFAOYSA-N 1-[2-[5-(cyclopropylmethoxy)benzimidazol-1-yl]quinolin-8-yl]piperidin-4-amine Chemical compound C1CC(N)CCN1C1=CC=CC2=CC=C(N3C4=CC=C(OCC5CC5)C=C4N=C3)N=C12 GJHVPIXOGJZNNP-UHFFFAOYSA-N 0.000 claims description 5
IAFYSPXKLJSJPA-UHFFFAOYSA-N 1-[2-[5-(pyridin-3-ylmethoxy)benzimidazol-1-yl]quinolin-8-yl]piperidin-4-amine Chemical compound C1CC(N)CCN1C1=CC=CC2=CC=C(N3C4=CC=C(OCC=5C=NC=CC=5)C=C4N=C3)N=C12 IAFYSPXKLJSJPA-UHFFFAOYSA-N 0.000 claims description 5
XROUPEKOUWUJQC-UHFFFAOYSA-N 1-[2-[5-(pyridin-4-ylmethoxy)benzimidazol-1-yl]quinolin-8-yl]piperidin-4-amine Chemical compound C1CC(N)CCN1C1=CC=CC2=CC=C(N3C4=CC=C(OCC=5C=CN=CC=5)C=C4N=C3)N=C12 XROUPEKOUWUJQC-UHFFFAOYSA-N 0.000 claims description 5
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 5
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 5
ZZHQDJNRIHLNIC-UHFFFAOYSA-N 1-[2-[5-[3-(dimethylamino)propoxy]benzimidazol-1-yl]quinolin-8-yl]piperidin-4-amine Chemical compound C1=NC2=CC(OCCCN(C)C)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CCC(N)CC1 ZZHQDJNRIHLNIC-UHFFFAOYSA-N 0.000 claims description 5
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 5
PQJHEPRSJAIZJL-UHFFFAOYSA-N 1-[4-[2-(5-ethoxybenzimidazol-1-yl)quinolin-8-yl]phenyl]-n-methylmethanamine Chemical compound C1=NC2=CC(OCC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2C1=CC=C(CNC)C=C1 PQJHEPRSJAIZJL-UHFFFAOYSA-N 0.000 claims description 5
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 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
XKHSFCASBYQFPQ-UHFFFAOYSA-N 1-[[4-[2-[5-(2-methoxyethoxy)benzimidazol-1-yl]quinolin-8-yl]phenyl]methyl]piperidin-4-amine Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2C(C=C1)=CC=C1CN1CCC(N)CC1 XKHSFCASBYQFPQ-UHFFFAOYSA-N 0.000 claims description 5
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 5
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 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
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
HVNSTUXYSKBEHF-UHFFFAOYSA-N 2-amino-1-[4-[2-[5-(2-methoxyethoxy)benzimidazol-1-yl]quinolin-8-yl]piperazin-1-yl]-2-methylpropan-1-one Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CCN(C(=O)C(C)(C)N)CC1 HVNSTUXYSKBEHF-UHFFFAOYSA-N 0.000 claims description 5
MAFWKRLAGPFUAY-UHFFFAOYSA-N 2-amino-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)CC1 MAFWKRLAGPFUAY-UHFFFAOYSA-N 0.000 claims description 5
FXSMUXMWLPKHBW-UHFFFAOYSA-N 3-[2-[5-(2-methoxyethoxy)benzimidazol-1-yl]quinolin-8-yl]-3-azabicyclo[3.1.0]hexan-6-amine Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CC2C(N)C2C1 FXSMUXMWLPKHBW-UHFFFAOYSA-N 0.000 claims description 5
ZOFPMZDYESPUJS-UHFFFAOYSA-N 4-[2-[5-(3-aminopropoxy)benzimidazol-1-yl]quinolin-8-yl]phenol Chemical compound C1=NC2=CC(OCCCN)=CC=C2N1C(N=C12)=CC=C1C=CC=C2C1=CC=C(O)C=C1 ZOFPMZDYESPUJS-UHFFFAOYSA-N 0.000 claims description 5
VFWVITQDTNOYNN-UHFFFAOYSA-N 4-methyl-1-[2-(5-phenylmethoxybenzimidazol-1-yl)quinolin-8-yl]piperidin-4-ol Chemical compound C1CC(C)(O)CCN1C1=CC=CC2=CC=C(N3C4=CC=C(OCC=5C=CC=CC=5)C=C4N=C3)N=C12 VFWVITQDTNOYNN-UHFFFAOYSA-N 0.000 claims description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
125000000304 alkynyl group Chemical group 0.000 claims description 5
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 5
IFUQDRSHJDUXDO-UHFFFAOYSA-N (3-aminopyrrolidin-1-yl)-[2-[5-(cyclopropylmethoxy)benzimidazol-1-yl]quinolin-8-yl]methanone Chemical compound C1C(N)CCN1C(=O)C1=CC=CC2=CC=C(N3C4=CC=C(OCC5CC5)C=C4N=C3)N=C12 IFUQDRSHJDUXDO-UHFFFAOYSA-N 0.000 claims description 4
TWLLKADWWLFSJJ-UHFFFAOYSA-N 1-[2-(5-ethoxybenzimidazol-1-yl)quinolin-8-yl]piperidin-4-amine Chemical compound C1=NC2=CC(OCC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CCC(N)CC1 TWLLKADWWLFSJJ-UHFFFAOYSA-N 0.000 claims description 4
LHDXMKIZLCGVIL-UHFFFAOYSA-N 1-[2-(5-methoxybenzimidazol-1-yl)quinolin-8-yl]-n-methylpiperidin-4-amine Chemical compound C1CC(NC)CCN1C1=CC=CC2=CC=C(N3C4=CC=C(OC)C=C4N=C3)N=C12 LHDXMKIZLCGVIL-UHFFFAOYSA-N 0.000 claims description 4
ZPCBPHZWHMRXLJ-UHFFFAOYSA-N 1-[2-(benzimidazol-1-yl)quinolin-8-yl]piperidin-4-amine Chemical compound C1CC(N)CCN1C1=CC=CC2=CC=C(N3C4=CC=CC=C4N=C3)N=C12 ZPCBPHZWHMRXLJ-UHFFFAOYSA-N 0.000 claims description 4
LWSBNWLLDYXSGC-UHFFFAOYSA-N 1-[2-[5-(3-methoxyphenyl)benzimidazol-1-yl]quinolin-8-yl]piperidin-4-amine Chemical compound COC1=CC=CC(C=2C=C3N=CN(C3=CC=2)C=2N=C3C(N4CCC(N)CC4)=CC=CC3=CC=2)=C1 LWSBNWLLDYXSGC-UHFFFAOYSA-N 0.000 claims description 4
HIEZOGPUHPBCLN-UHFFFAOYSA-N 1-[2-[5-(4-methoxyphenyl)benzimidazol-1-yl]quinolin-8-yl]piperidin-4-amine Chemical compound C1=CC(OC)=CC=C1C1=CC=C(N(C=N2)C=3N=C4C(N5CCC(N)CC5)=CC=CC4=CC=3)C2=C1 HIEZOGPUHPBCLN-UHFFFAOYSA-N 0.000 claims description 4
WSHPGNLRMOQYGC-UHFFFAOYSA-N 1-[2-[5-(6-methoxypyridin-3-yl)benzimidazol-1-yl]quinolin-8-yl]piperidin-4-amine Chemical compound C1=NC(OC)=CC=C1C1=CC=C(N(C=N2)C=3N=C4C(N5CCC(N)CC5)=CC=CC4=CC=3)C2=C1 WSHPGNLRMOQYGC-UHFFFAOYSA-N 0.000 claims description 4
AFOPQAHUVGEVHH-UHFFFAOYSA-N 1-[2-[5-[4-(methylaminomethyl)phenyl]benzimidazol-1-yl]quinolin-8-yl]piperidin-4-amine Chemical compound C1=CC(CNC)=CC=C1C1=CC=C(N(C=N2)C=3N=C4C(N5CCC(N)CC5)=CC=CC4=CC=3)C2=C1 AFOPQAHUVGEVHH-UHFFFAOYSA-N 0.000 claims description 4
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 4
GBWNEGOGPYFPLH-UHFFFAOYSA-N 1-[8-(4-aminopiperidin-1-yl)quinolin-2-yl]benzimidazole-5-carboxylic acid Chemical compound C1CC(N)CCN1C1=CC=CC2=CC=C(N3C4=CC=C(C=C4N=C3)C(O)=O)N=C12 GBWNEGOGPYFPLH-UHFFFAOYSA-N 0.000 claims description 4
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 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
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 4
OPIXUUPBVRVBHC-UHFFFAOYSA-N 2-[5-(2-methoxyethoxy)benzimidazol-1-yl]-8-pyridin-3-ylquinoline Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2C1=CC=CN=C1 OPIXUUPBVRVBHC-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
ZCIMJNMVKBSSNV-UHFFFAOYSA-N 4-[2-[5-[3-(dimethylamino)propoxy]benzimidazol-1-yl]quinolin-8-yl]phenol Chemical compound C1=NC2=CC(OCCCN(C)C)=CC=C2N1C(N=C12)=CC=C1C=CC=C2C1=CC=C(O)C=C1 ZCIMJNMVKBSSNV-UHFFFAOYSA-N 0.000 claims description 4
AWDSFJCNNJDBHR-UHFFFAOYSA-N 5-[2-[5-(2-methoxyethoxy)benzimidazol-1-yl]quinolin-8-yl]-1,3,4-oxadiazol-2-amine Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2C1=NN=C(N)O1 AWDSFJCNNJDBHR-UHFFFAOYSA-N 0.000 claims description 4
125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 4
125000005865 C2-C10alkynyl group Chemical group 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
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 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
AZNVSUCMHARAQH-UHFFFAOYSA-N methyl 2-[5-(2-methoxyethoxy)benzimidazol-1-yl]quinoline-8-carboxylate Chemical compound C1=CC=C(C(=O)OC)C2=NC(N3C4=CC=C(C=C4N=C3)OCCOC)=CC=C21 AZNVSUCMHARAQH-UHFFFAOYSA-N 0.000 claims description 4
150000004702 methyl esters Chemical class 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
FRHAKEFJJZWAPH-UHFFFAOYSA-N tert-butyl n-[1-[[4-[2-[5-(2-methoxyethoxy)benzimidazol-1-yl]quinolin-8-yl]phenyl]methyl]piperidin-4-yl]carbamate Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2C(C=C1)=CC=C1CN1CCC(NC(=O)OC(C)(C)C)CC1 FRHAKEFJJZWAPH-UHFFFAOYSA-N 0.000 claims description 4
BHFNNIGVTSAIGD-QGZVFWFLSA-N (3r)-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-QGZVFWFLSA-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
HECMDMMIJKYNSI-UHFFFAOYSA-N 1-[2-(5-ethoxybenzimidazol-1-yl)quinolin-8-yl]piperidin-4-ol Chemical compound C1=NC2=CC(OCC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CCC(O)CC1 HECMDMMIJKYNSI-UHFFFAOYSA-N 0.000 claims description 3
FXOHLCWIANAHOI-UHFFFAOYSA-N 1-[2-(5-methoxybenzimidazol-1-yl)quinolin-8-yl]-4-(methylaminomethyl)piperidin-4-ol Chemical compound C1CC(CNC)(O)CCN1C1=CC=CC2=CC=C(N3C4=CC=C(OC)C=C4N=C3)N=C12 FXOHLCWIANAHOI-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
VILDEPQDSOIOON-UHFFFAOYSA-N 1-[2-(5-methoxybenzimidazol-1-yl)quinolin-8-yl]pyrrolidin-3-amine Chemical compound C1=NC2=CC(OC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CCC(N)C1 VILDEPQDSOIOON-UHFFFAOYSA-N 0.000 claims description 3
INBYXZYOANPYLM-UHFFFAOYSA-N 1-[2-(5-pyridin-3-ylbenzimidazol-1-yl)quinolin-8-yl]piperidin-4-amine Chemical compound C1CC(N)CCN1C1=CC=CC2=CC=C(N3C4=CC=C(C=C4N=C3)C=3C=NC=CC=3)N=C12 INBYXZYOANPYLM-UHFFFAOYSA-N 0.000 claims description 3
IFQQXXHMLIGGLT-UHFFFAOYSA-N 1-[2-(6-methoxybenzimidazol-1-yl)quinolin-8-yl]piperidin-4-amine Chemical compound C12=CC(OC)=CC=C2N=CN1C(N=C12)=CC=C1C=CC=C2N1CCC(N)CC1 IFQQXXHMLIGGLT-UHFFFAOYSA-N 0.000 claims description 3
RESUNCDPOUAYHI-UHFFFAOYSA-N 1-[2-[5-(2-methoxyethoxy)benzimidazol-1-yl]quinolin-8-yl]-n,n-dimethylpiperidin-4-amine Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CCC(N(C)C)CC1 RESUNCDPOUAYHI-UHFFFAOYSA-N 0.000 claims description 3
CWVKHNCHHXOTNS-UHFFFAOYSA-N 1-[2-[5-(2-methoxyethoxy)benzimidazol-1-yl]quinolin-8-yl]-n-(pyridin-2-ylmethyl)piperidin-4-amine Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N(CC1)CCC1NCC1=CC=CC=N1 CWVKHNCHHXOTNS-UHFFFAOYSA-N 0.000 claims description 3
SJRWBGNQLJNBIJ-UHFFFAOYSA-N 1-[2-[5-(2-methoxyethoxy)benzimidazol-1-yl]quinolin-8-yl]-n-(pyridin-3-ylmethyl)piperidin-4-amine Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N(CC1)CCC1NCC1=CC=CN=C1 SJRWBGNQLJNBIJ-UHFFFAOYSA-N 0.000 claims description 3
LDRLUICQSMZEMX-UHFFFAOYSA-N 1-[2-[5-(trifluoromethoxy)benzimidazol-1-yl]quinolin-8-yl]piperidin-4-amine Chemical compound C1CC(N)CCN1C1=CC=CC2=CC=C(N3C4=CC=C(OC(F)(F)F)C=C4N=C3)N=C12 LDRLUICQSMZEMX-UHFFFAOYSA-N 0.000 claims description 3
VVUAOWZIYJULDG-UHFFFAOYSA-N 1-[2-[5-[2-(dimethylamino)ethoxy]benzimidazol-1-yl]quinolin-8-yl]-4-methylpiperidin-4-ol Chemical compound C1=NC2=CC(OCCN(C)C)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CCC(C)(O)CC1 VVUAOWZIYJULDG-UHFFFAOYSA-N 0.000 claims description 3
WXZRIHBJAUPFMW-UHFFFAOYSA-N 1-[2-[5-[2-(dimethylamino)ethoxy]benzimidazol-1-yl]quinolin-8-yl]piperidin-4-amine Chemical compound C1=NC2=CC(OCCN(C)C)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CCC(N)CC1 WXZRIHBJAUPFMW-UHFFFAOYSA-N 0.000 claims description 3
AOHXNZRIZPSDMN-UHFFFAOYSA-N 1-[8-(4-aminopiperidin-1-yl)quinolin-2-yl]-n,n-dimethylbenzimidazole-5-sulfonamide Chemical compound C1=NC2=CC(S(=O)(=O)N(C)C)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CCC(N)CC1 AOHXNZRIZPSDMN-UHFFFAOYSA-N 0.000 claims description 3
NLHBUULSJQVWNI-UHFFFAOYSA-N 1-[[1-[2-[5-(2-methoxyethoxy)benzimidazol-1-yl]quinolin-8-yl]piperidin-4-yl]methyl]pyrrolidin-3-ol Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N(CC1)CCC1CN1CCC(O)C1 NLHBUULSJQVWNI-UHFFFAOYSA-N 0.000 claims description 3
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 3
HIIDGEOICCJQKQ-UHFFFAOYSA-N 2-[2-(5-methoxybenzimidazol-1-yl)quinolin-8-yl]oxy-n,n-dimethylethanamine Chemical compound C1=CC=C(OCCN(C)C)C2=NC(N3C4=CC=C(C=C4N=C3)OC)=CC=C21 HIIDGEOICCJQKQ-UHFFFAOYSA-N 0.000 claims description 3
JSONYJOFNDRWJF-UHFFFAOYSA-N 2-[2-(5-methoxybenzimidazol-1-yl)quinolin-8-yl]oxyethanamine Chemical compound C1=CC=C(OCCN)C2=NC(N3C4=CC=C(C=C4N=C3)OC)=CC=C21 JSONYJOFNDRWJF-UHFFFAOYSA-N 0.000 claims description 3
XZBJMDCMEXXOPG-UHFFFAOYSA-N 2-[5-(2-methoxyethoxy)benzimidazol-1-yl]-8-(6-methoxypyridin-3-yl)quinoline Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2C1=CC=C(OC)N=C1 XZBJMDCMEXXOPG-UHFFFAOYSA-N 0.000 claims description 3
BRGGWBRIFFJGCZ-UHFFFAOYSA-N 2-[5-(2-methoxyethoxy)benzimidazol-1-yl]-8-[4-(pyridin-2-ylmethyl)piperazin-1-yl]quinoline Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N(CC1)CCN1CC1=CC=CC=N1 BRGGWBRIFFJGCZ-UHFFFAOYSA-N 0.000 claims description 3
BXVVAXVBRRJWJZ-UHFFFAOYSA-N 2-[5-(2-methoxyethoxy)benzimidazol-1-yl]-8-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]quinoline Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2C(C=C1)=CC=C1CN1CCN(C)CC1 BXVVAXVBRRJWJZ-UHFFFAOYSA-N 0.000 claims description 3
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 3
MEDDVVQDNZFOEG-UHFFFAOYSA-N 2-amino-n-[1-[2-[5-(2-methoxyethoxy)benzimidazol-1-yl]quinolin-8-yl]piperidin-4-yl]-2-methylpropanamide Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CCC(NC(=O)C(C)(C)N)CC1 MEDDVVQDNZFOEG-UHFFFAOYSA-N 0.000 claims description 3
WOKWXFPZMKKQRP-UHFFFAOYSA-N 2-amino-n-[1-[2-[5-(2-methoxyethoxy)benzimidazol-1-yl]quinolin-8-yl]piperidin-4-yl]acetamide Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CCC(NC(=O)CN)CC1 WOKWXFPZMKKQRP-UHFFFAOYSA-N 0.000 claims description 3
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 3
ARTNWTWQSRCHCO-UHFFFAOYSA-N 4-[(cyclopropylamino)methyl]-1-[2-[5-(2-methoxyethoxy)benzimidazol-1-yl]quinolin-8-yl]piperidin-4-ol Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N(CC1)CCC1(O)CNC1CC1 ARTNWTWQSRCHCO-UHFFFAOYSA-N 0.000 claims description 3
KTFSNPSVBSRYLH-UHFFFAOYSA-N 4-[[4-[2-[5-(2-methoxyethoxy)benzimidazol-1-yl]quinolin-8-yl]phenyl]methyl]morpholine Chemical compound C1=NC2=CC(OCCOC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2C(C=C1)=CC=C1CN1CCOCC1 KTFSNPSVBSRYLH-UHFFFAOYSA-N 0.000 claims description 3
ITALWILCQCRYPF-UHFFFAOYSA-N 6-[2-(5-methoxybenzimidazol-1-yl)quinolin-8-yl]-1-oxa-6-azaspiro[2.5]octane Chemical compound C1=NC2=CC(OC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N(CC1)CCC21CO2 ITALWILCQCRYPF-UHFFFAOYSA-N 0.000 claims description 3
GBQYBSDAYIFCME-UHFFFAOYSA-N [1-[2-(5-methoxybenzimidazol-1-yl)quinolin-8-yl]piperidin-4-yl]urea Chemical compound C1=NC2=CC(OC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CCC(NC(N)=O)CC1 GBQYBSDAYIFCME-UHFFFAOYSA-N 0.000 claims description 3
RHVNLVYQHGUDSU-UHFFFAOYSA-N [2-[5-(cyclopropylmethoxy)benzimidazol-1-yl]quinolin-8-yl]-morpholin-4-ylmethanone Chemical compound C=1C=CC2=CC=C(N3C4=CC=C(OCC5CC5)C=C4N=C3)N=C2C=1C(=O)N1CCOCC1 RHVNLVYQHGUDSU-UHFFFAOYSA-N 0.000 claims description 3
RNFRZTOGJWTFJF-UHFFFAOYSA-N [2-[5-(cyclopropylmethoxy)benzimidazol-1-yl]quinolin-8-yl]-piperidin-1-ylmethanone Chemical compound C=1C=CC2=CC=C(N3C4=CC=C(OCC5CC5)C=C4N=C3)N=C2C=1C(=O)N1CCCCC1 RNFRZTOGJWTFJF-UHFFFAOYSA-N 0.000 claims description 3
NBSZZANBJPAUBP-UHFFFAOYSA-N [4-[2-(5-methoxybenzimidazol-1-yl)quinolin-8-yl]phenyl]methanamine Chemical compound C1=NC2=CC(OC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2C1=CC=C(CN)C=C1 NBSZZANBJPAUBP-UHFFFAOYSA-N 0.000 claims description 3
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 3
YFCDXAVRQNSQCD-UHFFFAOYSA-N n-[1-[2-(5-methoxybenzimidazol-1-yl)quinolin-8-yl]piperidin-4-yl]acetamide Chemical compound C1=NC2=CC(OC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2N1CCC(NC(C)=O)CC1 YFCDXAVRQNSQCD-UHFFFAOYSA-N 0.000 claims description 3
MHPPMROJTTVGGF-UHFFFAOYSA-N n-[1-[2-[5-(cyclopropylmethoxy)benzimidazol-1-yl]quinolin-8-yl]piperidin-4-yl]acetamide Chemical compound C1CC(NC(=O)C)CCN1C1=CC=CC2=CC=C(N3C4=CC=C(OCC5CC5)C=C4N=C3)N=C12 MHPPMROJTTVGGF-UHFFFAOYSA-N 0.000 claims description 3
FAPPVAASLULQTM-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-2-(5-methoxybenzimidazol-1-yl)quinoline-8-carboxamide Chemical compound C1=CC=C(C(=O)NCCN(C)C)C2=NC(N3C4=CC=C(C=C4N=C3)OC)=CC=C21 FAPPVAASLULQTM-UHFFFAOYSA-N 0.000 claims description 3
UGJDDVXYOVKQKT-UHFFFAOYSA-N n-[[4-[2-(5-ethoxybenzimidazol-1-yl)quinolin-8-yl]phenyl]methyl]-2-methylpropan-2-amine Chemical compound C1=NC2=CC(OCC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2C1=CC=C(CNC(C)(C)C)C=C1 UGJDDVXYOVKQKT-UHFFFAOYSA-N 0.000 claims description 3
SSUFBTNTTOJTDF-UHFFFAOYSA-N n-[[4-[2-(5-ethoxybenzimidazol-1-yl)quinolin-8-yl]phenyl]methyl]cyclopropanamine Chemical compound C1=NC2=CC(OCC)=CC=C2N1C(N=C12)=CC=C1C=CC=C2C(C=C1)=CC=C1CNC1CC1 SSUFBTNTTOJTDF-UHFFFAOYSA-N 0.000 claims description 3
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NO20022556A 1999-11-30 2002-05-29 Nye benzoimidazolderivater nyttige som antiproliferative midler, samt anvendelse derav. NO324043B1 (no)

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US16821799P	1999-11-30	1999-11-30
PCT/IB2000/001636 WO2001040217A1 (en)	1999-11-30	2000-11-10	Novel benzoimidazole derivatives useful as antiproliferative agents

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NO20022556D0 NO20022556D0 (no)	2002-05-29
NO20022556L NO20022556L (no)	2002-07-29
NO324043B1 true NO324043B1 (no)	2007-07-30

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JP (2)	JP4522635B2 (da)
KR (1)	KR100479401B1 (da)
CN (2)	CN1402721A (da)
AP (1)	AP1895A (da)
AR (1)	AR026633A1 (da)
AT (1)	ATE316528T1 (da)
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KR100589032B1 (ko)	2000-10-20	2006-06-14	에자이 가부시키가이샤	질소 함유 방향환 유도체
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RS50800B (sr)	2010-08-31
TNSN00228A1 (fr)	2005-11-10
BG106812A (bg)	2003-01-31
GT200000198A (es)	2002-05-23
EP1235825B1 (en)	2006-01-25
YU30702A (sh)	2005-06-10
PA8507601A1 (es)	2003-02-14
AP2002002529A0 (en)	2002-06-30
EP1235825A1 (en)	2002-09-04
NO20022556L (no)	2002-07-29
JP4522635B2 (ja)	2010-08-11
BR0015911A (pt)	2002-08-06
CZ20021759A3 (cs)	2003-06-18
SK7172002A3 (en)	2004-07-07
IL149841A0 (en)	2002-11-10
HRP20020475A2 (en)	2005-10-31
PL355917A1 (en)	2004-05-31
EG24433A (en)	2009-06-25
DE60025747T2 (de)	2006-08-31
CA2392973C (en)	2007-05-15
IS2209B (is)	2007-02-15
CA2392973A1 (en)	2001-06-07
GEP20033141B (en)	2003-12-25
AU782077B2 (en)	2005-06-30
SV2002000232A (es)	2002-06-07
AR026633A1 (es)	2003-02-19
SK286773B6 (sk)	2009-05-07
NO20022556D0 (no)	2002-05-29
IS6341A (is)	2002-04-12
MY128765A (en)	2007-02-28
AP1895A (en)	2008-10-08
MA26847A1 (fr)	2004-12-20
US7019147B1 (en)	2006-03-28
DZ3327A1 (fr)	2001-06-07
NZ518280A (en)	2004-05-28
PL201784B1 (pl)	2009-05-29
AU1048001A (en)	2001-06-12
EE05350B1 (et)	2010-10-15
CO5251455A1 (es)	2003-02-28
KR20020059827A (ko)	2002-07-13
ZA200204244B (en)	2003-05-28
EE200200276A (et)	2003-06-16
HUP0203725A3 (en)	2004-05-28
TWI258475B (en)	2006-07-21
EA200200509A1 (ru)	2002-10-31
EA005407B1 (ru)	2005-02-24
HUP0203725A2 (hu)	2003-02-28
HU230829B1 (en)	2018-08-28
CR6643A (es)	2003-11-07
CN1402721A (zh)	2003-03-12
HRP20020475B1 (en)	2007-06-30
PE20010899A1 (es)	2001-09-05
DK1235825T3 (da)	2006-05-15
IL149841A (en)	2008-07-08
KR100479401B1 (ko)	2005-03-28
JP2007126468A (ja)	2007-05-24
CN101289442A (zh)	2008-10-22
DE60025747D1 (de)	2006-04-13
BG65862B1 (bg)	2010-03-31
CZ300789B6 (cs)	2009-08-12
JP2003515603A (ja)	2003-05-07
ATE316528T1 (de)	2006-02-15
CU23132A3 (es)	2006-05-22
WO2001040217A1 (en)	2001-06-07
TR200201430T2 (tr)	2003-01-21
SI1235825T1 (sl)	2006-06-30
ES2256052T3 (es)	2006-07-16
MXPA02005343A (es)	2002-12-11
UA75055C2 (uk)	2006-03-15

Publication	Publication Date	Title
CA2392973C (en)	2007-05-15	Benzoimidazole derivatives useful as antiproliferative agents
AU2008272641B2 (en)	2013-08-29	Benzimidazole derivatives
CA2495577C (en)	2010-06-15	Novel benzoimidazole derivatives useful as antiproliferative agents
NO322297B1 (no)	2006-09-11	Substituerte bisycliske derivater, anvendelse derav samt farmasoytisk sammensetning.
OA12098A (en)	2006-05-04	Novel benzuoimidazole derivatives useful as antiproliferative agents.
UA81915C2 (en)	2008-02-25	Novel venzoimidazole derivatives useful as antiproliferative agents

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