ES2606638T3 - Derivados de furopiridina - Google Patents
Derivados de furopiridina Download PDFInfo
- Publication number
- ES2606638T3 ES2606638T3 ES13701707.5T ES13701707T ES2606638T3 ES 2606638 T3 ES2606638 T3 ES 2606638T3 ES 13701707 T ES13701707 T ES 13701707T ES 2606638 T3 ES2606638 T3 ES 2606638T3
- Authority
- ES
- Spain
- Prior art keywords
- furo
- phenyl
- pyridin
- benzamide
- methoxy
- Prior art date
- Legal status (The legal status 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 status listed.)
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- YRTCKZIKGWZNCU-UHFFFAOYSA-N furo[3,2-b]pyridine Chemical class C1=CC=C2OC=CC2=N1 YRTCKZIKGWZNCU-UHFFFAOYSA-N 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 192
- 150000003839 salts Chemical class 0.000 claims abstract description 68
- 239000000203 mixture Substances 0.000 claims abstract description 59
- 239000012453 solvate Substances 0.000 claims abstract description 26
- -1 2,3-dihydroxy-propyl Chemical group 0.000 claims description 79
- 206010028980 Neoplasm Diseases 0.000 claims description 75
- 238000011282 treatment Methods 0.000 claims description 61
- 238000000034 method Methods 0.000 claims description 35
- 239000003814 drug Substances 0.000 claims description 34
- 201000011510 cancer Diseases 0.000 claims description 33
- 239000004480 active ingredient Substances 0.000 claims description 28
- 230000002265 prevention Effects 0.000 claims description 28
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 20
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 17
- 206010012601 diabetes mellitus Diseases 0.000 claims description 16
- 201000006417 multiple sclerosis Diseases 0.000 claims description 14
- 208000006673 asthma Diseases 0.000 claims description 12
- 210000004369 blood Anatomy 0.000 claims description 12
- 239000008280 blood Substances 0.000 claims description 12
- 229940079593 drug Drugs 0.000 claims description 10
- 208000010668 atopic eczema Diseases 0.000 claims description 9
- 206010025135 lupus erythematosus Diseases 0.000 claims description 8
- 230000002503 metabolic effect Effects 0.000 claims description 8
- 206010052779 Transplant rejections Diseases 0.000 claims description 7
- 230000006806 disease prevention Effects 0.000 claims description 7
- 206010006187 Breast cancer Diseases 0.000 claims description 6
- 208000026310 Breast neoplasm Diseases 0.000 claims description 6
- 201000004681 Psoriasis Diseases 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 230000000172 allergic effect Effects 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 210000001519 tissue Anatomy 0.000 claims description 6
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 5
- 208000036110 Neuroinflammatory disease Diseases 0.000 claims description 5
- 210000004556 brain Anatomy 0.000 claims description 5
- 208000035250 cutaneous malignant susceptibility to 1 melanoma Diseases 0.000 claims description 5
- 230000001900 immune effect Effects 0.000 claims description 5
- 210000004185 liver Anatomy 0.000 claims description 5
- 210000004072 lung Anatomy 0.000 claims description 5
- 201000001441 melanoma Diseases 0.000 claims description 5
- 210000002784 stomach Anatomy 0.000 claims description 5
- 230000009885 systemic effect Effects 0.000 claims description 5
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 claims description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 208000024827 Alzheimer disease Diseases 0.000 claims description 4
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 4
- 241000222722 Leishmania <genus> Species 0.000 claims description 4
- 241000186367 Mycobacterium avium Species 0.000 claims description 4
- 208000025747 Rheumatic disease Diseases 0.000 claims description 4
- 208000021386 Sjogren Syndrome Diseases 0.000 claims description 4
- 230000001363 autoimmune Effects 0.000 claims description 4
- 210000000988 bone and bone Anatomy 0.000 claims description 4
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- 230000004968 inflammatory condition Effects 0.000 claims description 4
- 210000000936 intestine Anatomy 0.000 claims description 4
- 210000003734 kidney Anatomy 0.000 claims description 4
- KHDOMUSXNPQCSA-UHFFFAOYSA-N n-(3-aminocyclobutyl)-3-[2-(3,4,5-trimethoxyphenyl)furo[3,2-b]pyridin-7-yl]benzamide Chemical compound COC1=C(OC)C(OC)=CC(C=2OC3=C(C=4C=C(C=CC=4)C(=O)NC4CC(N)C4)C=CN=C3C=2)=C1 KHDOMUSXNPQCSA-UHFFFAOYSA-N 0.000 claims description 4
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 4
- 201000008482 osteoarthritis Diseases 0.000 claims description 4
- 230000000552 rheumatic effect Effects 0.000 claims description 4
- DYZNJAFKKBMRGS-UHFFFAOYSA-N 2-[5-[2-(3,4,5-trimethoxyphenyl)furo[3,2-b]pyridin-7-yl]benzimidazol-1-yl]ethanamine Chemical compound COC1=C(OC)C(OC)=CC(C=2OC3=C(C=4C=C5N=CN(CCN)C5=CC=4)C=CN=C3C=2)=C1 DYZNJAFKKBMRGS-UHFFFAOYSA-N 0.000 claims description 3
- 206010016654 Fibrosis Diseases 0.000 claims description 3
- 241000725303 Human immunodeficiency virus Species 0.000 claims description 3
- 208000023105 Huntington disease Diseases 0.000 claims description 3
- 210000003679 cervix uteri Anatomy 0.000 claims description 3
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- 230000004770 neurodegeneration Effects 0.000 claims description 3
- 210000000056 organ Anatomy 0.000 claims description 3
- 210000002307 prostate Anatomy 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 230000001732 thrombotic effect Effects 0.000 claims description 3
- 210000001685 thyroid gland Anatomy 0.000 claims description 3
- 210000003932 urinary bladder Anatomy 0.000 claims description 3
- 239000003981 vehicle Substances 0.000 claims description 3
- HILFSSCAZSRZQW-CQSZACIVSA-N (1r)-1-[4-methoxy-3-[2-(3,4,5-trimethoxyphenyl)furo[3,2-b]pyridin-7-yl]phenyl]ethanamine Chemical compound COC1=CC=C([C@@H](C)N)C=C1C1=CC=NC2=C1OC(C=1C=C(OC)C(OC)=C(OC)C=1)=C2 HILFSSCAZSRZQW-CQSZACIVSA-N 0.000 claims description 2
- XQHYPUUVRMNBNG-UHFFFAOYSA-N 2-[6-[2-(3,4,5-trimethoxyphenyl)furo[3,2-b]pyridin-7-yl]benzimidazol-1-yl]ethanamine Chemical compound COC1=C(OC)C(OC)=CC(C=2OC3=C(C=4C=C5N(CCN)C=NC5=CC=4)C=CN=C3C=2)=C1 XQHYPUUVRMNBNG-UHFFFAOYSA-N 0.000 claims description 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 2
- UCSPLPMXSGHGSK-UHFFFAOYSA-N 3-(2-aminoethyl)-5-[2-(3,4,5-trimethoxyphenyl)furo[3,2-b]pyridin-7-yl]-1h-benzimidazol-2-one Chemical compound COC1=C(OC)C(OC)=CC(C=2OC3=C(C=4C=C5N(CCN)C(=O)NC5=CC=4)C=CN=C3C=2)=C1 UCSPLPMXSGHGSK-UHFFFAOYSA-N 0.000 claims description 2
- VQXBWCFFBVMQIQ-UHFFFAOYSA-N 3-[2-(5-carbamoyl-2-methoxyphenyl)furo[3,2-b]pyridin-7-yl]-4-methoxybenzamide Chemical compound COC1=CC=C(C(N)=O)C=C1C1=CC2=NC=CC(C=3C(=CC=C(C=3)C(N)=O)OC)=C2O1 VQXBWCFFBVMQIQ-UHFFFAOYSA-N 0.000 claims description 2
- CXHCEHXSQNLOMK-UHFFFAOYSA-N 3-[2-[4-(2-aminoethoxy)-2-methoxyphenyl]furo[3,2-b]pyridin-7-yl]-n-(2-hydroxyethyl)benzamide Chemical compound COC1=CC(OCCN)=CC=C1C1=CC2=NC=CC(C=3C=C(C=CC=3)C(=O)NCCO)=C2O1 CXHCEHXSQNLOMK-UHFFFAOYSA-N 0.000 claims description 2
- KHIYSPUVTJVSCN-UHFFFAOYSA-N 3-[3-[2-(3,4,5-trimethoxyphenyl)furo[3,2-b]pyridin-7-yl]-1h-1,2,4-triazol-5-yl]propan-1-amine Chemical compound COC1=C(OC)C(OC)=CC(C=2OC3=C(C=4N=C(CCCN)NN=4)C=CN=C3C=2)=C1 KHIYSPUVTJVSCN-UHFFFAOYSA-N 0.000 claims description 2
- AJECSQREYRXVFL-UHFFFAOYSA-N 3-[7-(1-ethylpyrazol-4-yl)furo[3,2-b]pyridin-2-yl]-4-methoxybenzamide Chemical compound C1=NN(CC)C=C1C1=CC=NC2=C1OC(C=1C(=CC=C(C=1)C(N)=O)OC)=C2 AJECSQREYRXVFL-UHFFFAOYSA-N 0.000 claims description 2
- USNBLJNUUVHIDJ-UHFFFAOYSA-N 3-[7-(1h-imidazol-5-yl)furo[3,2-b]pyridin-2-yl]-4-methoxybenzamide Chemical compound COC1=CC=C(C(N)=O)C=C1C1=CC2=NC=CC(C=3NC=NC=3)=C2O1 USNBLJNUUVHIDJ-UHFFFAOYSA-N 0.000 claims description 2
- TWCBTXQXUXKMEN-UHFFFAOYSA-N 3-[7-(2,6-dimethoxyphenyl)furo[3,2-b]pyridin-2-yl]-4-methoxybenzamide Chemical compound COC1=CC=C(C(N)=O)C=C1C1=CC2=NC=CC(C=3C(=CC=CC=3OC)OC)=C2O1 TWCBTXQXUXKMEN-UHFFFAOYSA-N 0.000 claims description 2
- ADLGASXDXNSLPK-UHFFFAOYSA-N 3-[7-(2,6-dimethoxyphenyl)furo[3,2-b]pyridin-2-yl]-4-methoxybenzenesulfonamide Chemical compound COC1=CC=C(S(N)(=O)=O)C=C1C1=CC2=NC=CC(C=3C(=CC=CC=3OC)OC)=C2O1 ADLGASXDXNSLPK-UHFFFAOYSA-N 0.000 claims description 2
- WOQBETCWFONTMZ-UHFFFAOYSA-N 3-[7-(2,6-dimethoxyphenyl)furo[3,2-b]pyridin-2-yl]-4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1C1=CC2=NC=CC(C=3C(=CC=CC=3OC)OC)=C2O1 WOQBETCWFONTMZ-UHFFFAOYSA-N 0.000 claims description 2
- YPPYMRYPYBAGPB-UHFFFAOYSA-N 3-[7-(2,6-dimethoxyphenyl)furo[3,2-b]pyridin-2-yl]-4-propan-2-ylbenzamide Chemical compound COC1=CC=CC(OC)=C1C1=CC=NC2=C1OC(C=1C(=CC=C(C=1)C(N)=O)C(C)C)=C2 YPPYMRYPYBAGPB-UHFFFAOYSA-N 0.000 claims description 2
- OUAYYJWEMUJVMO-UHFFFAOYSA-N 3-[7-(2,6-dimethoxyphenyl)furo[3,2-b]pyridin-2-yl]-n-(2-hydroxy-3-methoxypropyl)-4-methoxybenzamide Chemical compound COCC(O)CNC(=O)C1=CC=C(OC)C(C=2OC3=C(C=4C(=CC=CC=4OC)OC)C=CN=C3C=2)=C1 OUAYYJWEMUJVMO-UHFFFAOYSA-N 0.000 claims description 2
- BIGNZGQQFWMHLE-UHFFFAOYSA-N 3-[7-(3,5-dimethoxypyridin-4-yl)furo[3,2-b]pyridin-2-yl]-4-methoxybenzamide Chemical compound COC1=CC=C(C(N)=O)C=C1C1=CC2=NC=CC(C=3C(=CN=CC=3OC)OC)=C2O1 BIGNZGQQFWMHLE-UHFFFAOYSA-N 0.000 claims description 2
- NIYQRODSWDGFHF-UHFFFAOYSA-N 3-[7-(3h-benzimidazol-5-yl)furo[3,2-b]pyridin-2-yl]-4-methoxybenzamide Chemical compound COC1=CC=C(C(N)=O)C=C1C1=CC2=NC=CC(C=3C=C4NC=NC4=CC=3)=C2O1 NIYQRODSWDGFHF-UHFFFAOYSA-N 0.000 claims description 2
- KVUPDMRAUVXUGE-UHFFFAOYSA-N 3-[7-(6-fluoro-4-methylpyridin-3-yl)furo[3,2-b]pyridin-2-yl]-4-methoxybenzamide Chemical compound COC1=CC=C(C(N)=O)C=C1C1=CC2=NC=CC(C=3C(=CC(F)=NC=3)C)=C2O1 KVUPDMRAUVXUGE-UHFFFAOYSA-N 0.000 claims description 2
- PZNLJZOEXSIGGH-UHFFFAOYSA-N 3-[7-[2-(2-aminoethylamino)pyridin-4-yl]furo[3,2-b]pyridin-2-yl]-4-methoxybenzamide Chemical compound COC1=CC=C(C(N)=O)C=C1C1=CC2=NC=CC(C=3C=C(NCCN)N=CC=3)=C2O1 PZNLJZOEXSIGGH-UHFFFAOYSA-N 0.000 claims description 2
- WHQQPMNPCQGOGF-UHFFFAOYSA-N 3-[7-[2-[(2-aminocyclohexyl)amino]pyridin-4-yl]furo[3,2-b]pyridin-2-yl]-4-methoxybenzamide Chemical compound COC1=CC=C(C(N)=O)C=C1C1=CC2=NC=CC(C=3C=C(NC4C(CCCC4)N)N=CC=3)=C2O1 WHQQPMNPCQGOGF-UHFFFAOYSA-N 0.000 claims description 2
- WHQQPMNPCQGOGF-VQTJNVASSA-N 3-[7-[2-[[(1r,2s)-2-aminocyclohexyl]amino]pyridin-4-yl]furo[3,2-b]pyridin-2-yl]-4-methoxybenzamide Chemical compound COC1=CC=C(C(N)=O)C=C1C1=CC2=NC=CC(C=3C=C(N[C@H]4[C@H](CCCC4)N)N=CC=3)=C2O1 WHQQPMNPCQGOGF-VQTJNVASSA-N 0.000 claims description 2
- WHQQPMNPCQGOGF-UXHICEINSA-N 3-[7-[2-[[(1s,2r)-2-aminocyclohexyl]amino]pyridin-4-yl]furo[3,2-b]pyridin-2-yl]-4-methoxybenzamide Chemical compound COC1=CC=C(C(N)=O)C=C1C1=CC2=NC=CC(C=3C=C(N[C@@H]4[C@@H](CCCC4)N)N=CC=3)=C2O1 WHQQPMNPCQGOGF-UXHICEINSA-N 0.000 claims description 2
- KUJQQKJOXKEHOV-FCHUYYIVSA-N 3-[7-[3-[[(1r,2s)-2-aminocyclohexyl]carbamoyl]phenyl]furo[3,2-b]pyridin-2-yl]-4-methoxybenzamide Chemical compound COC1=CC=C(C(N)=O)C=C1C1=CC2=NC=CC(C=3C=C(C=CC=3)C(=O)N[C@H]3[C@H](CCCC3)N)=C2O1 KUJQQKJOXKEHOV-FCHUYYIVSA-N 0.000 claims description 2
- JGLKATRZWOIEDE-UHFFFAOYSA-N 3-[7-[5-(2-aminoethylcarbamoyl)-2-methoxyphenyl]furo[3,2-b]pyridin-2-yl]-4-methoxybenzamide Chemical compound COC1=CC=C(C(N)=O)C=C1C1=CC2=NC=CC(C=3C(=CC=C(C=3)C(=O)NCCN)OC)=C2O1 JGLKATRZWOIEDE-UHFFFAOYSA-N 0.000 claims description 2
- KCSMGVQXTKQGTL-UHFFFAOYSA-N 4-[2-(3,4,5-trimethoxyphenyl)furo[3,2-b]pyridin-7-yl]-1h-pyridin-2-one Chemical compound COC1=C(OC)C(OC)=CC(C=2OC3=C(C4=CC(=O)NC=C4)C=CN=C3C=2)=C1 KCSMGVQXTKQGTL-UHFFFAOYSA-N 0.000 claims description 2
- DVUFRPUVRCXUQA-FCHUYYIVSA-N 4-[7-[3-[[(1r,2s)-2-aminocyclohexyl]carbamoyl]phenyl]furo[3,2-b]pyridin-2-yl]-3-fluorobenzamide Chemical compound N[C@H]1CCCC[C@H]1NC(=O)C1=CC=CC(C=2C=3OC(=CC=3N=CC=2)C=2C(=CC(=CC=2)C(N)=O)F)=C1 DVUFRPUVRCXUQA-FCHUYYIVSA-N 0.000 claims description 2
- HLSBEORXFRGGGC-UHFFFAOYSA-N 4-amino-3-[7-(2,6-dimethoxyphenyl)furo[3,2-b]pyridin-2-yl]benzamide Chemical compound COC1=CC=CC(OC)=C1C1=CC=NC2=C1OC(C=1C(=CC=C(C=1)C(N)=O)N)=C2 HLSBEORXFRGGGC-UHFFFAOYSA-N 0.000 claims description 2
- XJQLQCDBENCACG-UHFFFAOYSA-N 4-methoxy-3-[7-(1h-pyrazol-5-yl)furo[3,2-b]pyridin-2-yl]benzenesulfonamide Chemical compound COC1=CC=C(S(N)(=O)=O)C=C1C1=CC2=NC=CC(C=3NN=CC=3)=C2O1 XJQLQCDBENCACG-UHFFFAOYSA-N 0.000 claims description 2
- BTXUZNOHEDGSQH-UHFFFAOYSA-N 4-methoxy-3-[7-(1h-pyrazol-5-yl)furo[3,2-b]pyridin-2-yl]benzonitrile Chemical compound COC1=CC=C(C#N)C=C1C1=CC2=NC=CC(C=3NN=CC=3)=C2O1 BTXUZNOHEDGSQH-UHFFFAOYSA-N 0.000 claims description 2
- WSXWUQPJNBHSDL-UHFFFAOYSA-N 4-methoxy-3-[7-(1h-pyrrol-3-yl)furo[3,2-b]pyridin-2-yl]benzamide Chemical compound COC1=CC=C(C(N)=O)C=C1C1=CC2=NC=CC(C3=CNC=C3)=C2O1 WSXWUQPJNBHSDL-UHFFFAOYSA-N 0.000 claims description 2
- INPOOGUPKOTWLE-UHFFFAOYSA-N 4-methoxy-3-[7-(2-methoxy-5-sulfamoylphenyl)furo[3,2-b]pyridin-2-yl]benzamide Chemical compound COC1=CC=C(C(N)=O)C=C1C1=CC2=NC=CC(C=3C(=CC=C(C=3)S(N)(=O)=O)OC)=C2O1 INPOOGUPKOTWLE-UHFFFAOYSA-N 0.000 claims description 2
- HJUPWLFRQVKHIG-UHFFFAOYSA-N 4-methoxy-3-[7-(6-methoxy-3h-benzimidazol-5-yl)furo[3,2-b]pyridin-2-yl]benzamide Chemical compound COC1=CC=C(C(N)=O)C=C1C1=CC2=NC=CC(C=3C(=CC=4N=CNC=4C=3)OC)=C2O1 HJUPWLFRQVKHIG-UHFFFAOYSA-N 0.000 claims description 2
- ISSFGCAYEQOOFV-UHFFFAOYSA-N 5-[2-(3,4,5-trimethoxyphenyl)furo[3,2-b]pyridin-7-yl]-1h-pyridin-2-one Chemical compound COC1=C(OC)C(OC)=CC(C=2OC3=C(C4=CNC(=O)C=C4)C=CN=C3C=2)=C1 ISSFGCAYEQOOFV-UHFFFAOYSA-N 0.000 claims description 2
- NOUXCWDXMHILSU-UHFFFAOYSA-N 7-(1h-pyrrol-3-yl)-2-(3,4,5-trimethoxyphenyl)furo[3,2-b]pyridine Chemical compound COC1=C(OC)C(OC)=CC(C=2OC3=C(C4=CNC=C4)C=CN=C3C=2)=C1 NOUXCWDXMHILSU-UHFFFAOYSA-N 0.000 claims description 2
- ZGBQWEBYCVOXLU-UHFFFAOYSA-N 7-(2,6-dimethoxyphenyl)-2-[2-methoxy-5-(2h-tetrazol-5-yl)phenyl]furo[3,2-b]pyridine Chemical compound COC1=CC=C(C2=NNN=N2)C=C1C(OC1=2)=CC1=NC=CC=2C1=C(OC)C=CC=C1OC ZGBQWEBYCVOXLU-UHFFFAOYSA-N 0.000 claims description 2
- QOGVNYXXDAIKIW-UHFFFAOYSA-N 7-(3,5-dimethoxypyridin-4-yl)-2-(3,4,5-trimethoxyphenyl)furo[3,2-b]pyridine Chemical compound COC1=C(OC)C(OC)=CC(C=2OC3=C(C=4C(=CN=CC=4OC)OC)C=CN=C3C=2)=C1 QOGVNYXXDAIKIW-UHFFFAOYSA-N 0.000 claims description 2
- CTDWAPSLJADBCI-UHFFFAOYSA-N 7-(3h-benzimidazol-5-yl)-2-(5-ethyl-2-methoxyphenyl)furo[3,2-b]pyridine Chemical compound CCC1=CC=C(OC)C(C=2OC3=C(C=4C=C5NC=NC5=CC=4)C=CN=C3C=2)=C1 CTDWAPSLJADBCI-UHFFFAOYSA-N 0.000 claims description 2
- NHPDEOQVVYRYOU-UHFFFAOYSA-N 7-(6-methoxy-3h-benzimidazol-5-yl)-2-(3,4,5-trimethoxyphenyl)furo[3,2-b]pyridine Chemical compound COC1=C(OC)C(OC)=CC(C=2OC3=C(C=4C(=CC=5N=CNC=5C=4)OC)C=CN=C3C=2)=C1 NHPDEOQVVYRYOU-UHFFFAOYSA-N 0.000 claims description 2
- KDEJMYRGHOTWRU-UHFFFAOYSA-N 7-(6-methyl-1h-indazol-5-yl)-2-(3,4,5-trimethoxyphenyl)furo[3,2-b]pyridine Chemical compound COC1=C(OC)C(OC)=CC(C=2OC3=C(C=4C(=CC=5NN=CC=5C=4)C)C=CN=C3C=2)=C1 KDEJMYRGHOTWRU-UHFFFAOYSA-N 0.000 claims description 2
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- NPAFSJLVOPCNGA-UHFFFAOYSA-N COc1ccc(cc1-c1ccnc2cc(oc12)-c1cc(OC)c(OC)c(OC)c1)C(=O)NCCCN Chemical compound COc1ccc(cc1-c1ccnc2cc(oc12)-c1cc(OC)c(OC)c(OC)c1)C(=O)NCCCN NPAFSJLVOPCNGA-UHFFFAOYSA-N 0.000 claims description 2
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- DLQNVHOGEMCQNX-FCHUYYIVSA-N N-[(1R,2S)-2-aminocyclohexyl]-3-[2-(4-hydroxy-2-methoxyphenyl)furo[3,2-b]pyridin-7-yl]benzamide Chemical compound COc1cc(O)ccc1-c1cc2nccc(-c3cccc(c3)C(=O)N[C@@H]3CCCC[C@@H]3N)c2o1 DLQNVHOGEMCQNX-FCHUYYIVSA-N 0.000 claims description 2
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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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- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
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Landscapes
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12001154 | 2012-02-21 | ||
| EP12001154 | 2012-02-21 | ||
| PCT/EP2013/000188 WO2013124025A1 (en) | 2012-02-21 | 2013-01-22 | Furopyridine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2606638T3 true ES2606638T3 (es) | 2017-03-24 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES13701707.5T Active ES2606638T3 (es) | 2012-02-21 | 2013-01-22 | Derivados de furopiridina |
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| Country | Link |
|---|---|
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| EP (1) | EP2817313B1 (enExample) |
| JP (1) | JP6097770B2 (enExample) |
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| KR20150074007A (ko) * | 2012-10-26 | 2015-07-01 | 에프. 호프만-라 로슈 아게 | 3,4-이치환된 1h-피라졸 및 4,5-이치환된 티아졸 syk 억제제 |
| CZ305472B6 (cs) * | 2014-04-30 | 2015-10-14 | Masarykova Univerzita | Substituované furo[3,2-b]pyridiny pro použití jako léčiva |
| AU2016287335B2 (en) * | 2015-06-29 | 2020-01-23 | Merck Patent Gmbh | TBK/IKKepsilon inhibitor compounds and uses thereof |
| KR20200116481A (ko) * | 2018-01-29 | 2020-10-12 | 메르크 파텐트 게엠베하 | Gcn2 억제제 및 이의 용도 |
| US10793563B2 (en) | 2018-01-29 | 2020-10-06 | Merck Patent Gmbh | GCN2 inhibitors and uses thereof |
| AU2020242287A1 (en) | 2019-03-21 | 2021-09-02 | INSERM (Institut National de la Santé et de la Recherche Médicale) | A Dbait molecule in combination with kinase inhibitor for the treatment of cancer |
| JP7621275B2 (ja) * | 2019-05-09 | 2025-01-24 | ブリストル－マイヤーズ スクイブ カンパニー | 置換ベンズイミダゾロン化合物 |
| KR20220098759A (ko) | 2019-11-08 | 2022-07-12 | 인쎄름 (엥스띠뛰 나씨오날 드 라 쌍떼 에 드 라 흐쉐르슈 메디깔) | 키나제 억제제에 대해 내성을 획득한 암의 치료 방법 |
| WO2021148581A1 (en) | 2020-01-22 | 2021-07-29 | Onxeo | Novel dbait molecule and its use |
| EP4522623A1 (en) * | 2022-05-12 | 2025-03-19 | Skyhawk Therapeutics, Inc. | Compositions useful for modulating splicing |
| CN119948032A (zh) | 2022-08-09 | 2025-05-06 | 默克专利股份有限公司 | 呋喃并嘧啶衍生物 |
| WO2024033280A1 (en) | 2022-08-09 | 2024-02-15 | Merck Patent Gmbh | Furopyridin and furopyrimidin, inhibitors of pi4k, for use in the treatment of parasite infection and malaria |
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| SK72996A3 (en) * | 1995-06-07 | 1997-04-09 | Pfizer | Heterocyclic ring-fused pyrimidine derivatives and pharmaceutical compositions on their base |
| GB9624482D0 (en) | 1995-12-18 | 1997-01-15 | Zeneca Phaema S A | Chemical compounds |
| BR9707495A (pt) | 1996-02-13 | 1999-07-27 | Zeneca Ltd | Derivado de quinazolina processo para a preparação do mesmo composição farmacêutica e processo para a produç o de um efeito antiangiogênico e/ou de redução de permeabilidade vascular em um animal de sangue quente |
| JP4464466B2 (ja) | 1996-03-05 | 2010-05-19 | アストラゼネカ・ユーケイ・リミテッド | ４―アニリノキナゾリン誘導体 |
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| GB9714249D0 (en) | 1997-07-08 | 1997-09-10 | Angiogene Pharm Ltd | Vascular damaging agents |
| US6187777B1 (en) * | 1998-02-06 | 2001-02-13 | Amgen Inc. | Compounds and methods which modulate feeding behavior and related diseases |
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| GB9900752D0 (en) | 1999-01-15 | 1999-03-03 | Angiogene Pharm Ltd | Benzimidazole vascular damaging agents |
| WO2001047922A2 (en) * | 1999-12-24 | 2001-07-05 | Aventis Pharma Limited | Azaindoles |
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| US20020004511A1 (en) * | 2000-06-28 | 2002-01-10 | Luzzio Michael Joseph | Thiophene derivatives useful as anticancer agents |
| JP2004502766A (ja) | 2000-07-07 | 2004-01-29 | アンギオジェン・ファーマシューティカルズ・リミテッド | 血管損傷剤としてのコルヒノール誘導体 |
| CA2410562A1 (en) | 2000-07-07 | 2002-01-31 | Angiogene Pharmaceuticals Limited | Colchinol derivatives as angiogenesis inhibitors |
| US7834024B2 (en) | 2007-03-26 | 2010-11-16 | Rigel Pharmaceuticals, Inc. | Compositions and methods for inhibition of the JAK pathway |
| KR101773313B1 (ko) | 2008-04-16 | 2017-08-31 | 포톨라 파마슈티컬스, 인코포레이티드 | ｓｙｋ 또는 ＪＡＫ 키나제 억제제로서의 ２,６－디아미노-피리미딘－５－일－카르복스아미드 |
| TWI453207B (zh) | 2008-09-08 | 2014-09-21 | Signal Pharm Llc | 胺基三唑并吡啶，其組合物及使用其之治療方法 |
| AU2011295441B2 (en) * | 2010-08-27 | 2015-04-09 | Merck Patent Gmbh | Furopyridine derivatives |
| DE102011009961A1 (de) * | 2011-02-01 | 2012-08-02 | Merck Patent Gmbh | 7-Azaindolderivate |
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| EP2817313B1 (en) | 2016-09-07 |
| WO2013124025A1 (en) | 2013-08-29 |
| JP6097770B2 (ja) | 2017-03-15 |
| TW201336850A (zh) | 2013-09-16 |
| CA2863717C (en) | 2021-09-28 |
| JP2015508085A (ja) | 2015-03-16 |
| CN104114558A (zh) | 2014-10-22 |
| EP2817313A1 (en) | 2014-12-31 |
| AU2013224420B2 (en) | 2016-12-15 |
| CN104114558B (zh) | 2016-10-26 |
| AU2013224420A1 (en) | 2014-10-02 |
| CA2863717A1 (en) | 2013-08-29 |
| AR090105A1 (es) | 2014-10-22 |
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