MXPA06000919A - Inhibidores de quinasa de tienopiridina y furopiridina. - Google Patents
Inhibidores de quinasa de tienopiridina y furopiridina.Info
- Publication number
- MXPA06000919A MXPA06000919A MXPA06000919A MXPA06000919A MXPA06000919A MX PA06000919 A MXPA06000919 A MX PA06000919A MX PA06000919 A MXPA06000919 A MX PA06000919A MX PA06000919 A MXPA06000919 A MX PA06000919A MX PA06000919 A MXPA06000919 A MX PA06000919A
- Authority
- MX
- Mexico
- Prior art keywords
- alkyl
- group
- amino
- phenyl
- heteroaryl
- Prior art date
Links
- 229940043355 kinase inhibitor Drugs 0.000 title description 2
- 239000003757 phosphotransferase inhibitor Substances 0.000 title description 2
- YRTCKZIKGWZNCU-UHFFFAOYSA-N furo[3,2-b]pyridine Chemical compound C1=CC=C2OC=CC2=N1 YRTCKZIKGWZNCU-UHFFFAOYSA-N 0.000 title 1
- DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical compound C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 title 1
- 229940125670 thienopyridine Drugs 0.000 title 1
- 239000002175 thienopyridine Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 235
- 238000000034 method Methods 0.000 claims abstract description 44
- 238000011282 treatment Methods 0.000 claims abstract description 27
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 248
- 125000003118 aryl group Chemical group 0.000 claims description 248
- -1 coxy I-1 Chemical group 0.000 claims description 214
- 229910052739 hydrogen Inorganic materials 0.000 claims description 205
- 239000001257 hydrogen Substances 0.000 claims description 205
- 125000001072 heteroaryl group Chemical group 0.000 claims description 192
- 125000000623 heterocyclic group Chemical group 0.000 claims description 126
- 125000003545 alkoxy group Chemical group 0.000 claims description 110
- 125000001424 substituent group Chemical group 0.000 claims description 110
- 229910052736 halogen Inorganic materials 0.000 claims description 109
- 150000002367 halogens Chemical class 0.000 claims description 109
- 125000001188 haloalkyl group Chemical group 0.000 claims description 103
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 78
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 70
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 64
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 62
- 125000003342 alkenyl group Chemical group 0.000 claims description 62
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 61
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 61
- 229910052757 nitrogen Inorganic materials 0.000 claims description 53
- 125000000304 alkynyl group Chemical group 0.000 claims description 52
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 46
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 45
- 239000004202 carbamide Substances 0.000 claims description 45
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 41
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 39
- 150000003839 salts Chemical class 0.000 claims description 38
- 239000002253 acid Substances 0.000 claims description 36
- 229910052740 iodine Inorganic materials 0.000 claims description 30
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 30
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 28
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 27
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 26
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 25
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 21
- 239000008194 pharmaceutical composition Substances 0.000 claims description 20
- 125000004043 oxo group Chemical group O=* 0.000 claims description 19
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 102000001253 Protein Kinase Human genes 0.000 claims description 15
- 201000010099 disease Diseases 0.000 claims description 15
- 108060006633 protein kinase Proteins 0.000 claims description 15
- 125000005312 heteroarylalkynyl group Chemical group 0.000 claims description 13
- 125000004449 heterocyclylalkenyl group Chemical group 0.000 claims description 13
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 12
- 229910003827 NRaRb Inorganic materials 0.000 claims description 11
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 11
- 206010028980 Neoplasm Diseases 0.000 claims description 10
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 8
- 201000011510 cancer Diseases 0.000 claims description 8
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 8
- 125000005020 hydroxyalkenyl group Chemical group 0.000 claims description 8
- 101100481410 Mus musculus Tek gene Proteins 0.000 claims description 7
- 206010030113 Oedema Diseases 0.000 claims description 7
- 125000005080 alkoxycarbonylalkenyl group Chemical group 0.000 claims description 7
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 7
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 7
- 125000005019 carboxyalkenyl group Chemical group 0.000 claims description 7
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 7
- 125000005016 hydroxyalkynyl group Chemical group 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 101100481408 Danio rerio tie2 gene Proteins 0.000 claims description 6
- 125000005015 aryl alkynyl group Chemical group 0.000 claims description 6
- 208000015181 infectious disease Diseases 0.000 claims description 6
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 5
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 5
- 125000005356 cycloalkylalkenyl group Chemical group 0.000 claims description 5
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 5
- 206010016654 Fibrosis Diseases 0.000 claims description 4
- 201000004681 Psoriasis Diseases 0.000 claims description 4
- 108010053100 Vascular Endothelial Growth Factor Receptor-3 Proteins 0.000 claims description 4
- 102000016663 Vascular Endothelial Growth Factor Receptor-3 Human genes 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 4
- 229910052702 rhenium Inorganic materials 0.000 claims description 4
- 101100381481 Caenorhabditis elegans baz-2 gene Proteins 0.000 claims description 3
- 208000011231 Crohn disease Diseases 0.000 claims description 3
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 3
- 102100028198 Macrophage colony-stimulating factor 1 receptor Human genes 0.000 claims description 3
- 101710150918 Macrophage colony-stimulating factor 1 receptor Proteins 0.000 claims description 3
- 101100335081 Mus musculus Flt3 gene Proteins 0.000 claims description 3
- 101100372762 Rattus norvegicus Flt1 gene Proteins 0.000 claims description 3
- 125000005086 alkoxycarbonylalkynyl group Chemical group 0.000 claims description 3
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 3
- 230000001684 chronic effect Effects 0.000 claims description 3
- 125000005357 cycloalkylalkynyl group Chemical group 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000004967 formylalkyl group Chemical group 0.000 claims description 3
- 201000006417 multiple sclerosis Diseases 0.000 claims description 3
- 125000004971 nitroalkyl group Chemical group 0.000 claims description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
- 201000000306 sarcoidosis Diseases 0.000 claims description 3
- 206010043778 thyroiditis Diseases 0.000 claims description 3
- 208000005189 Embolism Diseases 0.000 claims description 2
- 201000009273 Endometriosis Diseases 0.000 claims description 2
- 206010018364 Glomerulonephritis Diseases 0.000 claims description 2
- 208000009889 Herpes Simplex Diseases 0.000 claims description 2
- 208000007514 Herpes zoster Diseases 0.000 claims description 2
- 241000725303 Human immunodeficiency virus Species 0.000 claims description 2
- 206010051151 Hyperviscosity syndrome Diseases 0.000 claims description 2
- 206010021143 Hypoxia Diseases 0.000 claims description 2
- 208000016604 Lyme disease Diseases 0.000 claims description 2
- 206010027295 Menometrorrhagia Diseases 0.000 claims description 2
- 208000010191 Osteitis Deformans Diseases 0.000 claims description 2
- 206010053869 POEMS syndrome Diseases 0.000 claims description 2
- 208000027868 Paget disease Diseases 0.000 claims description 2
- 206010034277 Pemphigoid Diseases 0.000 claims description 2
- 206010040047 Sepsis Diseases 0.000 claims description 2
- 201000005485 Toxoplasmosis Diseases 0.000 claims description 2
- 206010052779 Transplant rejections Diseases 0.000 claims description 2
- 208000006673 asthma Diseases 0.000 claims description 2
- 208000037976 chronic inflammation Diseases 0.000 claims description 2
- 230000006020 chronic inflammation Effects 0.000 claims description 2
- 230000007882 cirrhosis Effects 0.000 claims description 2
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 2
- 206010012601 diabetes mellitus Diseases 0.000 claims description 2
- 230000002526 effect on cardiovascular system Effects 0.000 claims description 2
- 230000004761 fibrosis Effects 0.000 claims description 2
- 230000007954 hypoxia Effects 0.000 claims description 2
- 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims description 2
- 208000014674 injury Diseases 0.000 claims description 2
- 208000028867 ischemia Diseases 0.000 claims description 2
- 206010025135 lupus erythematosus Diseases 0.000 claims description 2
- 208000027202 mammary Paget disease Diseases 0.000 claims description 2
- 208000030761 polycystic kidney disease Diseases 0.000 claims description 2
- 201000011461 pre-eclampsia Diseases 0.000 claims description 2
- 230000005855 radiation Effects 0.000 claims description 2
- 208000007056 sickle cell anemia Diseases 0.000 claims description 2
- 201000004595 synovitis Diseases 0.000 claims description 2
- 230000009885 systemic effect Effects 0.000 claims description 2
- 230000008733 trauma Effects 0.000 claims description 2
- 208000006542 von Hippel-Lindau disease Diseases 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 6
- FFQLXAQWHRYUNK-UHFFFAOYSA-N 1-[4-(4-amino-7-pyridin-3-ylthieno[3,2-c]pyridin-3-yl)phenyl]-3-(3-methylphenyl)urea Chemical compound CC1=CC=CC(NC(=O)NC=2C=CC(=CC=2)C=2C3=C(N)N=CC(=C3SC=2)C=2C=NC=CC=2)=C1 FFQLXAQWHRYUNK-UHFFFAOYSA-N 0.000 claims 1
- DZLQDRCSYQJHJG-UHFFFAOYSA-N 1-[4-(4-amino-7-pyridin-4-ylthieno[3,2-c]pyridin-3-yl)phenyl]-3-(2-fluoro-5-methylphenyl)urea Chemical compound CC1=CC=C(F)C(NC(=O)NC=2C=CC(=CC=2)C=2C3=C(N)N=CC(=C3SC=2)C=2C=CN=CC=2)=C1 DZLQDRCSYQJHJG-UHFFFAOYSA-N 0.000 claims 1
- KKYPRNBBPBRJQX-UHFFFAOYSA-N 1-[4-(4-amino-7-pyridin-4-ylthieno[3,2-c]pyridin-3-yl)phenyl]-3-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound C1=2SC=C(C=3C=CC(NC(=O)NC=4C(=CC=C(C=4)C(F)(F)F)F)=CC=3)C=2C(N)=NC=C1C1=CC=NC=C1 KKYPRNBBPBRJQX-UHFFFAOYSA-N 0.000 claims 1
- SBXVZMIZJGLIRS-UHFFFAOYSA-N 1-[4-(4-amino-7-pyrimidin-5-ylthieno[3,2-c]pyridin-3-yl)phenyl]-3-(3-methylphenyl)urea Chemical compound CC1=CC=CC(NC(=O)NC=2C=CC(=CC=2)C=2C3=C(N)N=CC(=C3SC=2)C=2C=NC=NC=2)=C1 SBXVZMIZJGLIRS-UHFFFAOYSA-N 0.000 claims 1
- NWTAZZIWWSKSOZ-UHFFFAOYSA-N 1-[4-[4-amino-7-(2-methoxypyrimidin-5-yl)thieno[3,2-c]pyridin-3-yl]phenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound C1=NC(OC)=NC=C1C1=CN=C(N)C2=C1SC=C2C(C=C1)=CC=C1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 NWTAZZIWWSKSOZ-UHFFFAOYSA-N 0.000 claims 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 1
- VBWIZSYFQSOUFQ-UHFFFAOYSA-N cyclohexanecarbonitrile Chemical compound N#CC1CCCCC1 VBWIZSYFQSOUFQ-UHFFFAOYSA-N 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 210000001672 ovary Anatomy 0.000 claims 1
- 230000002685 pulmonary effect Effects 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 93
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 abstract description 10
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 abstract description 10
- 239000000047 product Substances 0.000 description 185
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 172
- 238000005481 NMR spectroscopy Methods 0.000 description 148
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 137
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 129
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 115
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 105
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 82
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 48
- 239000000243 solution Substances 0.000 description 46
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 44
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 44
- 238000005160 1H NMR spectroscopy Methods 0.000 description 41
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
- 238000006243 chemical reaction Methods 0.000 description 38
- 125000001041 indolyl group Chemical group 0.000 description 38
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 37
- 238000004007 reversed phase HPLC Methods 0.000 description 36
- 235000019439 ethyl acetate Nutrition 0.000 description 35
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 33
- 239000000741 silica gel Substances 0.000 description 31
- 229910002027 silica gel Inorganic materials 0.000 description 31
- 229910052701 rubidium Inorganic materials 0.000 description 30
- 229960004979 fampridine Drugs 0.000 description 29
- 125000004076 pyridyl group Chemical group 0.000 description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 27
- 125000004414 alkyl thio group Chemical group 0.000 description 26
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 25
- QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 24
- 238000000746 purification Methods 0.000 description 23
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 22
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- 229940043376 ammonium acetate Drugs 0.000 description 22
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- 239000003112 inhibitor Substances 0.000 description 21
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 20
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 20
- 210000004027 cell Anatomy 0.000 description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 19
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 19
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- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 18
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 18
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- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 17
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- VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 9
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- YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 9
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- 241001465754 Metazoa Species 0.000 description 9
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
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- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Virology (AREA)
- Immunology (AREA)
- Diabetes (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Heart & Thoracic Surgery (AREA)
- Pulmonology (AREA)
- Cardiology (AREA)
- Hematology (AREA)
- Dermatology (AREA)
- Endocrinology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Urology & Nephrology (AREA)
- Rheumatology (AREA)
- Vascular Medicine (AREA)
- Molecular Biology (AREA)
- Neurosurgery (AREA)
- Emergency Medicine (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Transplantation (AREA)
- Ophthalmology & Optometry (AREA)
- Pain & Pain Management (AREA)
- Obesity (AREA)
- Reproductive Health (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/626,092 US20050020619A1 (en) | 2003-07-24 | 2003-07-24 | Thienopyridine kinase inhibitors |
| US10/838,132 US20050026944A1 (en) | 2003-07-24 | 2004-05-03 | Thienopyridine and furopyridine kinase inhibitors |
| PCT/US2004/024003 WO2005010009A1 (en) | 2003-07-24 | 2004-07-26 | Thienopyridine and furopyridine kinase inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA06000919A true MXPA06000919A (es) | 2006-05-04 |
Family
ID=34108157
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA06000919A MXPA06000919A (es) | 2003-07-24 | 2004-07-26 | Inhibidores de quinasa de tienopiridina y furopiridina. |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US20050026944A1 (https=) |
| EP (1) | EP1648905B1 (https=) |
| JP (1) | JP4707192B2 (https=) |
| KR (2) | KR101120936B1 (https=) |
| CN (1) | CN103087078A (https=) |
| AT (1) | ATE419253T1 (https=) |
| AU (2) | AU2004259765B2 (https=) |
| BR (1) | BRPI0412894A (https=) |
| CA (1) | CA2532982C (https=) |
| CY (1) | CY1111599T1 (https=) |
| DE (1) | DE602004018780D1 (https=) |
| DK (1) | DK1648905T3 (https=) |
| ES (1) | ES2319302T3 (https=) |
| IL (1) | IL173348A (https=) |
| MX (1) | MXPA06000919A (https=) |
| NZ (1) | NZ544712A (https=) |
| PL (1) | PL1648905T3 (https=) |
| PT (1) | PT1648905E (https=) |
| WO (1) | WO2005010009A1 (https=) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1620094A4 (en) * | 2003-05-06 | 2010-04-28 | Glaxosmithkline Llc | NEW CHEMICAL COMPOUNDS |
| US7899855B2 (en) * | 2003-09-08 | 2011-03-01 | Intel Corporation | Method, apparatus and instructions for parallel data conversions |
| GB0325836D0 (en) * | 2003-11-05 | 2003-12-10 | Celltech R&D Ltd | Biological products |
| TW200538453A (en) * | 2004-04-26 | 2005-12-01 | Bristol Myers Squibb Co | Bicyclic heterocycles as kinase inhibitors |
| US20050256154A1 (en) * | 2004-05-04 | 2005-11-17 | Kin-Chun Luk | 4-Amino-thieno[3,2-c]pyridine-7-carboxylic acid amides |
| US20060281768A1 (en) * | 2005-06-10 | 2006-12-14 | Gaul Michael D | Thienopyrimidine and thienopyridine kinase modulators |
| US7566721B2 (en) * | 2005-08-08 | 2009-07-28 | Osi Pharmaceuticals, Inc. | Substituted thienol[2,3-d]pyrimidines as kinase inhibitors |
| JP2009504692A (ja) * | 2005-08-16 | 2009-02-05 | エフ．ホフマン−ラ ロシュ アーゲー | 新規４−アミノ−チエノ［３，２−ｃ］ピリジン−７−カルボン酸アミド |
| CA2621830C (en) * | 2005-09-15 | 2013-12-03 | F. Hoffmann-La Roche Ag | 4-amino-thieno[3,2-c]pyridine-7-carboxylic acid derivatives |
| JP2009514899A (ja) * | 2005-11-04 | 2009-04-09 | スミスクライン ビーチャム コーポレーション | チエノピリジンＢ−Ｒａｆキナーゼ阻害剤 |
| CN101336244B (zh) * | 2005-12-08 | 2011-11-30 | 雅培制药有限公司 | 用作蛋白激酶抑制剂的9元杂二环化合物 |
| GB0525164D0 (en) | 2005-12-09 | 2006-01-18 | Xention Discovery Ltd | Compounds |
| TW200801008A (en) * | 2005-12-29 | 2008-01-01 | Abbott Lab | Protein kinase inhibitors |
| US7659283B2 (en) * | 2006-02-14 | 2010-02-09 | Vertex Pharmaceuticals Incorporated | Pyrrolo [3,2-C] pyridines useful as inhibitors of protein kinases |
| US7932390B2 (en) * | 2006-06-29 | 2011-04-26 | Hoffman-La Roche Inc. | Substituted thieno[3,2-C]pyridine carboxylic acid derivatives |
| US7994321B2 (en) | 2006-08-08 | 2011-08-09 | Hoffmann-La Roche Inc. | Substituted thieno[3,2-C]pyridine-7-carboxylic acid derivatives |
| WO2008018881A1 (en) * | 2006-08-10 | 2008-02-14 | Osi Pharmaceuticals, Inc. | 6,6-bicyclic ring substituted sulfur containing heterobicyclic protein kinase inhibitors |
| MX2010001636A (es) * | 2007-08-14 | 2010-03-15 | Hoffmann La Roche | Derivados de pirazolo[3,4-d]-pirimidina como agentes antiproliferativos. |
| AR070317A1 (es) * | 2008-02-06 | 2010-03-31 | Osi Pharm Inc | Furo (3,2-c) piridina y tieno (3,2-c) piridinas |
| CA2723358A1 (en) * | 2008-05-05 | 2009-11-12 | Allison B. Reiss | Method for improving cardiovascular risk profile of cox inhibitors |
| AR074481A1 (es) * | 2008-12-05 | 2011-01-19 | Abbott Lab | Derivados de tienopiridina como inhibidores de quinasa |
| EP2491030B1 (en) | 2009-10-22 | 2015-07-15 | Fibrotech Therapeutics PTY LTD | Fused ring analogues of anti-fibrotic agents |
| TWI482770B (zh) * | 2010-06-09 | 2015-05-01 | Abbvie Bahamas Ltd | 結晶型激酶抑制劑 |
| CA2802042A1 (en) * | 2010-06-09 | 2011-12-15 | Abbott Laboratories | Crystalline forms of kinase inhibitors |
| TWI492949B (zh) * | 2010-06-09 | 2015-07-21 | Abbvie Bahamas Ltd | 結晶型激酶抑制劑 |
| AU2011271518A1 (en) | 2010-07-02 | 2012-12-13 | Alcon Research, Ltd. | Compounds for the treatment of posterior segment disorders and diseases |
| RU2013120966A (ru) | 2010-10-08 | 2014-11-20 | Эббви Инк. | ФУРО[3,2-d]ПИРИМИДИНОВЫЕ СОЕДИНЕНИЯ |
| US8436179B2 (en) | 2011-07-20 | 2013-05-07 | Abbvie Inc. | Kinase inhibitor with improved solubility profile |
| CN103396414B (zh) * | 2013-07-16 | 2015-06-03 | 浙江医药高等专科学校 | 咪唑取代的噻唑并环己烷类化合物、及其抗肿瘤用途 |
| CN104945411B (zh) * | 2014-03-27 | 2018-07-31 | 南京勇山生物科技有限公司 | 噻吩并[3,2-c]吡啶类化合物、其制备方法及应用 |
| WO2015157360A1 (en) | 2014-04-08 | 2015-10-15 | Abbvie Inc. | Processes to make protein kinase inhibitors |
| WO2016047678A1 (ja) * | 2014-09-25 | 2016-03-31 | 武田薬品工業株式会社 | 複素環化合物 |
| CA3052036A1 (en) | 2017-02-03 | 2018-08-09 | Certa Therapeutics Pty Ltd. | Anti-fibrotic compounds |
| MX2023005747A (es) | 2020-11-18 | 2023-07-28 | Deciphera Pharmaceuticals Llc | Inhibidores de gcn2 y perk quinasas y metodos de uso de los mismos. |
| KR20240113496A (ko) | 2021-12-03 | 2024-07-22 | 데시페라 파마슈티칼스, 엘엘씨. | Gcn2 및 perk 키나아제 억제제로서의 헤테로고리 화합물 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2221213T3 (es) * | 1997-10-20 | 2004-12-16 | F. Hoffmann-La Roche Ag | Inhibidores de kinasa biciclicos. |
| WO2000038683A1 (en) * | 1998-12-23 | 2000-07-06 | Du Pont Pharmaceuticals Company | THROMBIN OR FACTOR Xa INHIBITORS |
| PL354241A1 (en) * | 1999-09-17 | 2003-12-29 | Abbott Gmbh & Co.Kgabbott Gmbh & Co.Kg | Kinase inhibitors as therapeutic agents |
| US6608053B2 (en) * | 2000-04-27 | 2003-08-19 | Yamanouchi Pharmaceutical Co., Ltd. | Fused heteroaryl derivatives |
| CN1186324C (zh) * | 2000-04-27 | 2005-01-26 | 山之内制药株式会社 | 稠合杂芳基衍生物 |
| EP1373240B1 (en) * | 2001-03-14 | 2005-06-15 | Eli Lilly And Company | Retinoid x receptor modulators |
| AU2002333524A1 (en) * | 2001-09-11 | 2003-03-24 | Glaxosmithkline K.K. | Furo-and thienopyrimidine derivatives as angiogenesis inhibitors |
| EP1620094A4 (en) * | 2003-05-06 | 2010-04-28 | Glaxosmithkline Llc | NEW CHEMICAL COMPOUNDS |
-
2004
- 2004-05-03 US US10/838,132 patent/US20050026944A1/en not_active Abandoned
- 2004-07-26 DK DK04779180T patent/DK1648905T3/da active
- 2004-07-26 AU AU2004259765A patent/AU2004259765B2/en not_active Ceased
- 2004-07-26 AT AT04779180T patent/ATE419253T1/de active
- 2004-07-26 MX MXPA06000919A patent/MXPA06000919A/es active IP Right Grant
- 2004-07-26 EP EP04779180A patent/EP1648905B1/en not_active Expired - Lifetime
- 2004-07-26 JP JP2006521305A patent/JP4707192B2/ja not_active Expired - Fee Related
- 2004-07-26 BR BRPI0412894-0A patent/BRPI0412894A/pt not_active IP Right Cessation
- 2004-07-26 KR KR1020067001692A patent/KR101120936B1/ko not_active Expired - Fee Related
- 2004-07-26 PL PL04779180T patent/PL1648905T3/pl unknown
- 2004-07-26 WO PCT/US2004/024003 patent/WO2005010009A1/en not_active Ceased
- 2004-07-26 NZ NZ544712A patent/NZ544712A/en not_active IP Right Cessation
- 2004-07-26 DE DE602004018780T patent/DE602004018780D1/de not_active Expired - Lifetime
- 2004-07-26 CN CN2012105340956A patent/CN103087078A/zh active Pending
- 2004-07-26 ES ES04779180T patent/ES2319302T3/es not_active Expired - Lifetime
- 2004-07-26 CA CA2532982A patent/CA2532982C/en not_active Expired - Fee Related
- 2004-07-26 PT PT04779180T patent/PT1648905E/pt unknown
- 2004-07-26 KR KR1020117023338A patent/KR20110123797A/ko not_active Withdrawn
-
2006
- 2006-01-24 IL IL173348A patent/IL173348A/en not_active IP Right Cessation
-
2009
- 2009-03-12 CY CY20091100278T patent/CY1111599T1/el unknown
- 2009-12-22 AU AU2009251083A patent/AU2009251083B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| EP1648905A1 (en) | 2006-04-26 |
| KR20110123797A (ko) | 2011-11-15 |
| ES2319302T3 (es) | 2009-05-06 |
| AU2004259765B2 (en) | 2009-10-22 |
| US20050026944A1 (en) | 2005-02-03 |
| WO2005010009A1 (en) | 2005-02-03 |
| JP4707192B2 (ja) | 2011-06-22 |
| AU2004259765A1 (en) | 2005-02-03 |
| JP2006528646A (ja) | 2006-12-21 |
| CY1111599T1 (el) | 2015-10-07 |
| CA2532982C (en) | 2013-11-26 |
| EP1648905B1 (en) | 2008-12-31 |
| KR20060056344A (ko) | 2006-05-24 |
| BRPI0412894A (pt) | 2006-10-03 |
| NZ544712A (en) | 2009-09-25 |
| ATE419253T1 (de) | 2009-01-15 |
| AU2009251083A1 (en) | 2010-01-21 |
| AU2009251083B2 (en) | 2012-02-16 |
| CN103087078A (zh) | 2013-05-08 |
| DE602004018780D1 (de) | 2009-02-12 |
| IL173348A (en) | 2015-11-30 |
| KR101120936B1 (ko) | 2012-03-29 |
| IL173348A0 (en) | 2006-06-11 |
| DK1648905T3 (da) | 2009-03-30 |
| PT1648905E (pt) | 2009-04-08 |
| CA2532982A1 (en) | 2005-02-03 |
| PL1648905T3 (pl) | 2009-07-31 |
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