MX2010013549A - Imidazoles sustituidos con 2-piridilo, como inhibidores de alk4 y/o alk4. - Google Patents
Imidazoles sustituidos con 2-piridilo, como inhibidores de alk4 y/o alk4.Info
- Publication number
- MX2010013549A MX2010013549A MX2010013549A MX2010013549A MX2010013549A MX 2010013549 A MX2010013549 A MX 2010013549A MX 2010013549 A MX2010013549 A MX 2010013549A MX 2010013549 A MX2010013549 A MX 2010013549A MX 2010013549 A MX2010013549 A MX 2010013549A
- Authority
- MX
- Mexico
- Prior art keywords
- methylpyridin
- imidazol
- quinoline
- fluoro
- methyl
- Prior art date
Links
- 239000003112 inhibitor Substances 0.000 title claims abstract description 13
- 150000002460 imidazoles Chemical class 0.000 title claims description 6
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 title claims description 5
- -1 2-pyridyl-substituted imidazoles Chemical class 0.000 claims abstract description 561
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 21
- 201000010099 disease Diseases 0.000 claims abstract description 13
- 230000001404 mediated effect Effects 0.000 claims abstract description 10
- 238000011282 treatment Methods 0.000 claims abstract description 7
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 139
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 131
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 80
- 150000001875 compounds Chemical class 0.000 claims description 70
- 125000000217 alkyl group Chemical group 0.000 claims description 61
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 58
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 52
- 125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 claims description 35
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 24
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 22
- 125000004122 cyclic group Chemical group 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
- 101000799189 Homo sapiens Activin receptor type-1B Proteins 0.000 claims description 21
- 150000002367 halogens Chemical class 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 102100034134 Activin receptor type-1B Human genes 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims description 14
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims description 13
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 13
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 13
- 108020003175 receptors Proteins 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 11
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims description 11
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 11
- 241000124008 Mammalia Species 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 10
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 208000005069 pulmonary fibrosis Diseases 0.000 claims description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
- 241000282414 Homo sapiens Species 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 8
- 208000035475 disorder Diseases 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical compound C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000006279 3-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Br)=C1[H])C([H])([H])* 0.000 claims description 7
- 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims description 7
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 7
- 230000001684 chronic effect Effects 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 208000017169 kidney disease Diseases 0.000 claims description 7
- UIAJCOFJULVZHA-UHFFFAOYSA-N 6-[2-[[4-fluoro-3-(2-pyrrolidin-1-ylethoxy)phenyl]methyl]-5-(6-methylpyridin-2-yl)-1h-imidazol-4-yl]quinoline Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=C(OCCN4CCCC4)C(F)=CC=3)N2)C=2C=C3C=CC=NC3=CC=2)=N1 UIAJCOFJULVZHA-UHFFFAOYSA-N 0.000 claims description 6
- 206010016654 Fibrosis Diseases 0.000 claims description 6
- 206010028980 Neoplasm Diseases 0.000 claims description 6
- 125000004450 alkenylene group Chemical group 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000004419 alkynylene group Chemical group 0.000 claims description 6
- 230000004761 fibrosis Effects 0.000 claims description 6
- 208000015181 infectious disease Diseases 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 201000002793 renal fibrosis Diseases 0.000 claims description 6
- DISRINLOFKCEPS-UHFFFAOYSA-N 2-fluoro-n-(2-hydroxyethyl)-5-[[5-(6-methylpyridin-2-yl)-4-quinolin-6-yl-1h-imidazol-2-yl]methyl]benzamide Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=C(C(F)=CC=3)C(=O)NCCO)N2)C=2C=C3C=CC=NC3=CC=2)=N1 DISRINLOFKCEPS-UHFFFAOYSA-N 0.000 claims description 5
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 5
- 125000006509 3,4-difluorobenzyl group Chemical group [H]C1=C(F)C(F)=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 5
- 125000006281 4-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)C([H])([H])* 0.000 claims description 5
- 208000025865 Ulcer Diseases 0.000 claims description 5
- 229940079593 drug Drugs 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 239000012453 solvate Substances 0.000 claims description 5
- 231100000397 ulcer Toxicity 0.000 claims description 5
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 4
- PUGXCELHUHOMOZ-UHFFFAOYSA-N 2-[2-fluoro-5-[[5-(6-methylpyridin-2-yl)-4-quinolin-6-yl-1h-imidazol-2-yl]methyl]anilino]ethanol Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=C(NCCO)C(F)=CC=3)N2)C=2C=C3C=CC=NC3=CC=2)=N1 PUGXCELHUHOMOZ-UHFFFAOYSA-N 0.000 claims description 4
- ATPGFJSTYOQRHN-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[(3-chlorophenyl)methyl]-1h-imidazol-5-yl]-6-methylpyridine Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=C(Cl)C=CC=3)N2)C=2C=C3OCOC3=CC=2)=N1 ATPGFJSTYOQRHN-UHFFFAOYSA-N 0.000 claims description 4
- FYNWYMYWFIXHNO-UHFFFAOYSA-N 2-fluoro-5-[[5-(6-methylpyridin-2-yl)-4-quinolin-6-yl-1h-imidazol-2-yl]methyl]phenol Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=C(O)C(F)=CC=3)N2)C=2C=C3C=CC=NC3=CC=2)=N1 FYNWYMYWFIXHNO-UHFFFAOYSA-N 0.000 claims description 4
- PXQCXPMOMFHUNZ-UHFFFAOYSA-N 2-fluoro-5-[[5-(6-methylpyridin-2-yl)-4-quinoxalin-6-yl-1h-imidazol-2-yl]methyl]benzamide Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=C(C(F)=CC=3)C(N)=O)N2)C=2C=C3N=CC=NC3=CC=2)=N1 PXQCXPMOMFHUNZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
- HJEGDRFCTDDUOI-UHFFFAOYSA-N 6-[2-[[4-fluoro-3-(2-methoxyethoxy)phenyl]methyl]-5-(6-methylpyridin-2-yl)-1h-imidazol-4-yl]quinoline Chemical compound C1=C(F)C(OCCOC)=CC(CC=2NC(=C(N=2)C=2C=C3C=CC=NC3=CC=2)C=2N=C(C)C=CC=2)=C1 HJEGDRFCTDDUOI-UHFFFAOYSA-N 0.000 claims description 4
- NZJADIIOVAHUKP-UHFFFAOYSA-N 6-[5-(6-bromopyridin-2-yl)-2-[[3-(trifluoromethyl)phenyl]methyl]-1h-imidazol-4-yl]-2-methylquinoline Chemical compound C1=CC2=NC(C)=CC=C2C=C1C(=C(N1)C=2N=C(Br)C=CC=2)N=C1CC1=CC=CC(C(F)(F)F)=C1 NZJADIIOVAHUKP-UHFFFAOYSA-N 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 4
- 239000005711 Benzoic acid Substances 0.000 claims description 4
- 206010018364 Glomerulonephritis Diseases 0.000 claims description 4
- 206010019668 Hepatic fibrosis Diseases 0.000 claims description 4
- 206010020772 Hypertension Diseases 0.000 claims description 4
- 206010023421 Kidney fibrosis Diseases 0.000 claims description 4
- 206010027476 Metastases Diseases 0.000 claims description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- 208000007536 Thrombosis Diseases 0.000 claims description 4
- 206010052428 Wound Diseases 0.000 claims description 4
- 208000027418 Wounds and injury Diseases 0.000 claims description 4
- 235000010233 benzoic acid Nutrition 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 230000003176 fibrotic effect Effects 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 230000035876 healing Effects 0.000 claims description 4
- 230000009401 metastasis Effects 0.000 claims description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 230000002062 proliferating effect Effects 0.000 claims description 4
- 231100000241 scar Toxicity 0.000 claims description 4
- 230000036573 scar formation Effects 0.000 claims description 4
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 3
- NVWNMUAGXSVSPR-UHFFFAOYSA-N 2-[2-[(3-chlorophenyl)methyl]-4-(4-methoxyphenyl)-1h-imidazol-5-yl]-6-methylpyridine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2N=C(C)C=CC=2)NC(CC=2C=C(Cl)C=CC=2)=N1 NVWNMUAGXSVSPR-UHFFFAOYSA-N 0.000 claims description 3
- SDESXCNUVAHSRC-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[(3-fluorophenyl)methyl]-1h-imidazol-5-yl]-6-methylpyridine Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=C(F)C=CC=3)N2)C=2C=C3OCOC3=CC=2)=N1 SDESXCNUVAHSRC-UHFFFAOYSA-N 0.000 claims description 3
- NDFBPBOILTYFDS-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)-2-[(3-fluorophenyl)methyl]-1h-imidazol-5-yl]-6-methylpyridine Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=C(F)C=CC=3)N2)C=2C=CC(Cl)=CC=2)=N1 NDFBPBOILTYFDS-UHFFFAOYSA-N 0.000 claims description 3
- CTBNRVKKTIVRMA-UHFFFAOYSA-N 2-fluoro-5-[[5-(6-methylpyridin-2-yl)-4-quinolin-6-yl-1h-imidazol-2-yl]methyl]aniline Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=C(N)C(F)=CC=3)N2)C=2C=C3C=CC=NC3=CC=2)=N1 CTBNRVKKTIVRMA-UHFFFAOYSA-N 0.000 claims description 3
- 125000006288 3,5-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(C([H])=C1F)C([H])([H])* 0.000 claims description 3
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 3
- MWOZOGGQGOAMRN-UHFFFAOYSA-N 6-[2-[(2,4-dichlorophenyl)methyl]-5-(6-methylpyridin-2-yl)-1h-imidazol-4-yl]quinoline Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C(=CC(Cl)=CC=3)Cl)N2)C=2C=C3C=CC=NC3=CC=2)=N1 MWOZOGGQGOAMRN-UHFFFAOYSA-N 0.000 claims description 3
- NTQIOEHXAXASSK-UHFFFAOYSA-N 6-[2-[(3-bromo-4-methoxyphenyl)methyl]-5-(6-methylpyridin-2-yl)-1h-imidazol-4-yl]quinoxaline Chemical compound C1=C(Br)C(OC)=CC=C1CC1=NC(C=2C=C3N=CC=NC3=CC=2)=C(C=2N=C(C)C=CC=2)N1 NTQIOEHXAXASSK-UHFFFAOYSA-N 0.000 claims description 3
- SYYXJFOKMCYFLB-UHFFFAOYSA-N 6-[2-[(3-bromophenyl)methyl]-5-(6-bromopyridin-2-yl)-1h-imidazol-4-yl]quinoline Chemical compound BrC1=CC=CC(CC=2NC(=C(N=2)C=2C=C3C=CC=NC3=CC=2)C=2N=C(Br)C=CC=2)=C1 SYYXJFOKMCYFLB-UHFFFAOYSA-N 0.000 claims description 3
- RRPXQHPARPQTSF-UHFFFAOYSA-N 6-[2-[(4-fluoro-3-nitrophenyl)methyl]-5-(6-methylpyridin-2-yl)-1h-imidazol-4-yl]quinoline Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=C(C(F)=CC=3)[N+]([O-])=O)N2)C=2C=C3C=CC=NC3=CC=2)=N1 RRPXQHPARPQTSF-UHFFFAOYSA-N 0.000 claims description 3
- 208000024827 Alzheimer disease Diseases 0.000 claims description 3
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- 208000010228 Erectile Dysfunction Diseases 0.000 claims description 3
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- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims description 3
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- 208000004362 Penile Induration Diseases 0.000 claims description 3
- 208000020758 Peyronie disease Diseases 0.000 claims description 3
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- 201000009594 Systemic Scleroderma Diseases 0.000 claims description 3
- 206010042953 Systemic sclerosis Diseases 0.000 claims description 3
- 206010057469 Vascular stenosis Diseases 0.000 claims description 3
- DIUPBDXWGYGBIO-UHFFFAOYSA-N [2-fluoro-5-[[5-(6-methylpyridin-2-yl)-4-quinolin-6-yl-1h-imidazol-2-yl]methyl]phenyl]methanol Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=C(CO)C(F)=CC=3)N2)C=2C=C3C=CC=NC3=CC=2)=N1 DIUPBDXWGYGBIO-UHFFFAOYSA-N 0.000 claims description 3
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
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- 125000001624 naphthyl group Chemical group 0.000 claims description 3
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- NOHQXYWIGVREJK-UHFFFAOYSA-N 2-[2-fluoro-5-[[5-(6-methylpyridin-2-yl)-4-quinolin-6-yl-1h-imidazol-2-yl]methyl]phenoxy]ethanol Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=C(OCCO)C(F)=CC=3)N2)C=2C=C3C=CC=NC3=CC=2)=N1 NOHQXYWIGVREJK-UHFFFAOYSA-N 0.000 claims description 2
- LTSBAKXZLZWTJR-UHFFFAOYSA-N 2-[2-fluoro-5-[[5-(6-methylpyridin-2-yl)-4-quinoxalin-6-yl-1h-imidazol-2-yl]methyl]phenoxy]ethanol Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=C(OCCO)C(F)=CC=3)N2)C=2C=C3N=CC=NC3=CC=2)=N1 LTSBAKXZLZWTJR-UHFFFAOYSA-N 0.000 claims description 2
- RIMVKMGPBRMPLF-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[(2,4,5-trifluorophenyl)methyl]-1h-imidazol-5-yl]-6-methylpyridine Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C(=CC(F)=C(F)C=3)F)N2)C=2C=C3OCOC3=CC=2)=N1 RIMVKMGPBRMPLF-UHFFFAOYSA-N 0.000 claims description 2
- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 2
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 claims description 2
- NVYIWEQTAANTSQ-UHFFFAOYSA-N 6-[2-[(2,3-difluorophenyl)methyl]-5-(6-methylpyridin-2-yl)-1h-imidazol-4-yl]quinoline Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C(=C(F)C=CC=3)F)N2)C=2C=C3C=CC=NC3=CC=2)=N1 NVYIWEQTAANTSQ-UHFFFAOYSA-N 0.000 claims description 2
- IKPVNNIDBJIWPR-UHFFFAOYSA-N 6-[2-[(3,5-difluorophenyl)methyl]-5-(6-methylpyridin-2-yl)-1h-imidazol-4-yl]quinoline Chemical compound CC1=CC=CC(C2=C(N=C(CC=3C=C(F)C=C(F)C=3)N2)C=2C=C3C=CC=NC3=CC=2)=N1 IKPVNNIDBJIWPR-UHFFFAOYSA-N 0.000 claims description 2
- JSPFGXOXBICTCC-UHFFFAOYSA-N 6-[2-[(3-chloro-4-methoxyphenyl)methyl]-5-(6-methylpyridin-2-yl)-1h-imidazol-4-yl]quinoline Chemical compound C1=C(Cl)C(OC)=CC=C1CC1=NC(C=2C=C3C=CC=NC3=CC=2)=C(C=2N=C(C)C=CC=2)N1 JSPFGXOXBICTCC-UHFFFAOYSA-N 0.000 claims description 2
- MXXWWBIRBJHCOT-UHFFFAOYSA-N 6-[2-[(3-chloro-4-methoxyphenyl)methyl]-5-(6-methylpyridin-2-yl)-1h-imidazol-4-yl]quinoxaline Chemical compound C1=C(Cl)C(OC)=CC=C1CC1=NC(C=2C=C3N=CC=NC3=CC=2)=C(C=2N=C(C)C=CC=2)N1 MXXWWBIRBJHCOT-UHFFFAOYSA-N 0.000 claims description 2
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- 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
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- C—CHEMISTRY; METALLURGY
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- 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
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- C07—ORGANIC CHEMISTRY
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- 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
- C07D405/14—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 three or more hetero rings
Landscapes
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12/155,984 US20080319012A1 (en) | 2004-04-21 | 2008-06-12 | 2-Pyridyl substituted imidazoles as ALK5 and/or ALK4 inhibitors |
| PCT/IB2009/006398 WO2009150547A2 (en) | 2008-06-12 | 2009-06-11 | 2-pyridyl substituted imidazoles as alk4 and/or alk4 inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX2010013549A true MX2010013549A (es) | 2011-06-22 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| MX2010013549A MX2010013549A (es) | 2008-06-12 | 2009-06-11 | Imidazoles sustituidos con 2-piridilo, como inhibidores de alk4 y/o alk4. |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US20080319012A1 (enExample) |
| EP (1) | EP2303860A4 (enExample) |
| JP (1) | JP2011522877A (enExample) |
| KR (1) | KR101654859B1 (enExample) |
| CN (1) | CN102083811B (enExample) |
| AU (1) | AU2009259021A1 (enExample) |
| BR (1) | BRPI0909899A2 (enExample) |
| CA (1) | CA2727607A1 (enExample) |
| IL (1) | IL209915A (enExample) |
| MX (1) | MX2010013549A (enExample) |
| RU (1) | RU2011100781A (enExample) |
| WO (1) | WO2009150547A2 (enExample) |
| ZA (1) | ZA201100277B (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US20080319012A1 (en) | 2004-04-21 | 2008-12-25 | In2Gen Co., Ltd. | 2-Pyridyl substituted imidazoles as ALK5 and/or ALK4 inhibitors |
| WO2009123316A1 (ja) * | 2008-04-04 | 2009-10-08 | 武田薬品工業株式会社 | 複素環誘導体及びその用途 |
| USRE47141E1 (en) | 2010-06-29 | 2018-11-27 | EWHA University—Industry Collaboration Foundation | Methods of treating fibrosis, cancer and vascular injuries |
| US8513222B2 (en) | 2010-06-29 | 2013-08-20 | EWHA University—Industry Collaboration Foundation | Methods of treating fibrosis, cancer and vascular injuries |
| US8080568B1 (en) * | 2010-06-29 | 2011-12-20 | Ewha University - Industry Collaboration Foundation | 2-pyridyl substituted imidazoles as therapeutic ALK5 and/or ALK4 inhibitors |
| WO2012106343A2 (en) | 2011-02-01 | 2012-08-09 | The Board Of Trustees Of The University Of Illinois | Hdac inhibitors and therapeutic methods using the same |
| EP2731949B1 (en) * | 2011-07-13 | 2018-04-04 | TiumBio Co., Ltd. | 2-pyridyl substituted imidazoles as alk5 and/or alk4 inhibitors |
| MX2021006831A (es) | 2018-12-11 | 2021-07-02 | Theravance Biopharma R&D Ip Llc | Inhibidores de alk5. |
| CN114728941A (zh) * | 2019-11-22 | 2022-07-08 | 施万生物制药研发Ip有限责任公司 | 作为alk5抑制剂的经取代的1,5-萘啶或喹啉 |
| EP4087657A1 (en) | 2020-01-08 | 2022-11-16 | Synthis Therapeutics, Inc. | Alk5 inhibitor conjugates and uses thereof |
| AR122711A1 (es) * | 2020-06-25 | 2022-09-28 | Alchemedicine Inc | COMPUESTO HETEROCÍCLICO COMO INHIBIDOR DE CASEÍNA QUINASA 1d Y/O QUINASA 5 TIPO RECEPTOR DE ACTIVINA |
| EP4219453A4 (en) | 2020-09-28 | 2024-10-09 | Sichuan Kelun-Biotech Biopharmaceutical Co., Ltd. | PYRAZOLE COMPOUND AND ITS PREPARATION METHOD AND ITS USE |
| WO2024258967A1 (en) | 2023-06-13 | 2024-12-19 | Synthis Therapeutics, Inc. | Anti-cd5 antibodies and their uses |
Family Cites Families (11)
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| DE60001229T2 (de) | 1999-04-09 | 2003-10-30 | Smithkline Beecham Corp., Philadelphia | Triarylimidazole |
| AR029803A1 (es) * | 2000-02-21 | 2003-07-16 | Smithkline Beecham Plc | Imidazoles sustituidos con piridilo y composiciones farmaceuticas que las comprenden |
| GB0007405D0 (en) | 2000-03-27 | 2000-05-17 | Smithkline Beecham Corp | Compounds |
| GB0100762D0 (en) | 2001-01-11 | 2001-02-21 | Smithkline Beecham Plc | Novel use |
| EP1391452A4 (en) | 2001-05-25 | 2005-10-26 | Mochida Pharm Co Ltd | 4-HYDROXPIPERIDIN DERIVATIVE ANALGETIC EFFECT |
| AR039241A1 (es) | 2002-04-04 | 2005-02-16 | Biogen Inc | Heteroarilos trisustituidos y metodos para su produccion y uso de los mismos |
| OA12928A (en) * | 2002-09-18 | 2006-10-13 | Pfizer Prod Inc | Novel imidazole compounds as transforming growth factor (TGF) inhibitors. |
| US7250434B2 (en) * | 2003-12-22 | 2007-07-31 | Janssen Pharmaceutica N.V. | CCK-1 receptor modulators |
| US8420685B2 (en) * | 2004-04-21 | 2013-04-16 | Sk Chemicals Co., Ltd. | 2-pyridyl substituted imidazoles as ALK5 and/or ALK4 inhibitors |
| US20080319012A1 (en) * | 2004-04-21 | 2008-12-25 | In2Gen Co., Ltd. | 2-Pyridyl substituted imidazoles as ALK5 and/or ALK4 inhibitors |
| KR100749566B1 (ko) * | 2004-04-21 | 2007-08-16 | 이화여자대학교 산학협력단 | Ａｌｋ5 및/또는 ａｌｋ4 억제제로 유효한 2-피리딜이치환된 이미다졸 유도체 |
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2008
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2009
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- 2009-06-11 MX MX2010013549A patent/MX2010013549A/es active IP Right Grant
- 2009-06-11 KR KR1020117000260A patent/KR101654859B1/ko not_active Expired - Fee Related
- 2009-06-11 WO PCT/IB2009/006398 patent/WO2009150547A2/en not_active Ceased
- 2009-06-11 RU RU2011100781/04A patent/RU2011100781A/ru not_active Application Discontinuation
- 2009-06-11 BR BRPI0909899A patent/BRPI0909899A2/pt not_active IP Right Cessation
- 2009-06-11 EP EP09762075A patent/EP2303860A4/en not_active Withdrawn
- 2009-06-11 CN CN200980121870.1A patent/CN102083811B/zh not_active Expired - Fee Related
- 2009-06-11 AU AU2009259021A patent/AU2009259021A1/en not_active Abandoned
- 2009-06-11 JP JP2011513075A patent/JP2011522877A/ja active Pending
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2010
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2011
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Also Published As
| Publication number | Publication date |
|---|---|
| IL209915A0 (en) | 2011-02-28 |
| KR20110022662A (ko) | 2011-03-07 |
| ZA201100277B (en) | 2012-03-28 |
| EP2303860A4 (en) | 2011-07-06 |
| CA2727607A1 (en) | 2009-12-17 |
| US20080319012A1 (en) | 2008-12-25 |
| CN102083811A (zh) | 2011-06-01 |
| JP2011522877A (ja) | 2011-08-04 |
| AU2009259021A1 (en) | 2009-12-17 |
| RU2011100781A (ru) | 2012-07-20 |
| BRPI0909899A2 (pt) | 2016-02-16 |
| KR101654859B1 (ko) | 2016-09-07 |
| US20130245066A1 (en) | 2013-09-19 |
| WO2009150547A3 (en) | 2010-08-26 |
| WO2009150547A2 (en) | 2009-12-17 |
| IL209915A (en) | 2015-10-29 |
| EP2303860A2 (en) | 2011-04-06 |
| CN102083811B (zh) | 2014-01-22 |
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| Publication | Publication Date | Title |
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| DK2731949T3 (en) | 2-PYRIDYL-SUBSTITUTED IMIDAZOLS AS ALK5 AND / OR ALK4 INHIBITORS | |
| US8410146B2 (en) | 2-pyridyl substituted imidazoles as ALK5 and/or ALK4 inhibitors | |
| US7407958B2 (en) | 2-pyridyl substituted imidazoles as ALK5 and/or ALK4 inhibitors | |
| US8420685B2 (en) | 2-pyridyl substituted imidazoles as ALK5 and/or ALK4 inhibitors |
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