ES2797805T3 - Compuestos heterocíclicos tricíclicos sustituidos - Google Patents
Compuestos heterocíclicos tricíclicos sustituidos Download PDFInfo
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- ES2797805T3 ES2797805T3 ES16712645T ES16712645T ES2797805T3 ES 2797805 T3 ES2797805 T3 ES 2797805T3 ES 16712645 T ES16712645 T ES 16712645T ES 16712645 T ES16712645 T ES 16712645T ES 2797805 T3 ES2797805 T3 ES 2797805T3
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- Prior art keywords
- zero
- substituted
- alkyl
- crgrg
- aryl
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- 150000002391 heterocyclic compounds Chemical class 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 308
- 125000003118 aryl group Chemical group 0.000 claims abstract description 143
- -1 -OH Chemical group 0.000 claims abstract description 125
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 115
- 150000003839 salts Chemical class 0.000 claims abstract description 105
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 69
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract description 68
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 45
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 41
- 125000002950 monocyclic group Chemical group 0.000 claims abstract description 37
- 125000004452 carbocyclyl group Chemical group 0.000 claims abstract description 36
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 29
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 29
- 125000005843 halogen group Chemical group 0.000 claims abstract description 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 28
- 239000012453 solvate Substances 0.000 claims abstract description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 22
- 125000003709 fluoroalkyl group Chemical group 0.000 claims abstract description 20
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 19
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract description 18
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 16
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 14
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract description 13
- 125000002619 bicyclic group Chemical group 0.000 claims abstract description 12
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 11
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 11
- 125000005605 benzo group Chemical group 0.000 claims abstract description 10
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims abstract description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 4
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims abstract description 3
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims abstract description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 11
- 125000000217 alkyl group Chemical group 0.000 claims description 120
- ZVWSNJQNGVRIGG-UHFFFAOYSA-N N=1C=NC2=NC=C(CC2=1)O Chemical compound N=1C=NC2=NC=C(CC2=1)O ZVWSNJQNGVRIGG-UHFFFAOYSA-N 0.000 claims description 34
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 claims description 25
- 125000003545 alkoxy group Chemical group 0.000 claims description 24
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 23
- 238000011282 treatment Methods 0.000 claims description 23
- 229910052801 chlorine Inorganic materials 0.000 claims description 20
- 239000008194 pharmaceutical composition Substances 0.000 claims description 20
- 208000023275 Autoimmune disease Diseases 0.000 claims description 17
- WCJSZPKAHIGHSP-UHFFFAOYSA-N 11-[4-(2-hydroxypropan-2-yl)phenyl]-3-[2-(trifluoromethyl)phenyl]-2,7,12-triazatricyclo[6.4.0.02,6]dodeca-1(8),6,9,11-tetraen-5-ol Chemical compound OC(C)(C)C1=CC=C(C=C1)C1=CC=C2C(=N1)N1C(=N2)C(CC1C1=C(C=CC=C1)C(F)(F)F)O WCJSZPKAHIGHSP-UHFFFAOYSA-N 0.000 claims description 15
- 230000002757 inflammatory effect Effects 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 208000027866 inflammatory disease Diseases 0.000 claims description 13
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 125000001188 haloalkyl group Chemical group 0.000 claims description 10
- VKRVXXGHKNLUEU-UHFFFAOYSA-N 3-[2-fluoro-6-(trifluoromethyl)phenyl]-11-[4-(2-hydroxypropan-2-yl)phenyl]-2,7,12-triazatricyclo[6.4.0.02,6]dodeca-1(8),6,9,11-tetraen-5-ol Chemical compound FC1=C(C(=CC=C1)C(F)(F)F)C1CC(C2=NC=3C(=NC(=CC=3)C3=CC=C(C=C3)C(C)(C)O)N21)O VKRVXXGHKNLUEU-UHFFFAOYSA-N 0.000 claims description 8
- 238000002560 therapeutic procedure Methods 0.000 claims description 8
- XLDXEBXBEVPCDQ-UHFFFAOYSA-N 2-[4-[3-[2-(trifluoromethyl)phenyl]-2,7,12-triazatricyclo[6.4.0.02,6]dodeca-1(8),6,9,11-tetraen-11-yl]phenyl]propan-2-ol Chemical compound FC(C1=C(C=CC=C1)C1CCC2=NC=3C(=NC(=CC=3)C3=CC=C(C=C3)C(C)(C)O)N21)(F)F XLDXEBXBEVPCDQ-UHFFFAOYSA-N 0.000 claims description 7
- 239000003085 diluting agent Substances 0.000 claims description 7
- 201000010099 disease Diseases 0.000 claims description 7
- AQHQIKSWRGMNJB-UHFFFAOYSA-N 2-[4-[5-fluoro-3-[2-(trifluoromethyl)phenyl]-2,7,12-triazatricyclo[6.4.0.02,6]dodeca-1(8),6,9,11-tetraen-11-yl]phenyl]propan-2-ol Chemical compound FC1CC(N2C1=NC=1C2=NC(=CC=1)C1=CC=C(C=C1)C(C)(C)O)C1=C(C=CC=C1)C(F)(F)F AQHQIKSWRGMNJB-UHFFFAOYSA-N 0.000 claims description 6
- 206010003246 arthritis Diseases 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000002757 morpholinyl group Chemical group 0.000 claims description 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- CCYYYKOUISBKNQ-HSZRJFAPSA-N 2-[4-[(3R)-3-(2,5-dimethylphenyl)-2,7,12-triazatricyclo[6.4.0.02,6]dodeca-1(8),6,9,11-tetraen-11-yl]phenyl]propan-2-ol Chemical compound CC1=C(C=C(C=C1)C)[C@H]1CCC2=NC=3C(=NC(=CC=3)C3=CC=C(C=C3)C(C)(C)O)N21 CCYYYKOUISBKNQ-HSZRJFAPSA-N 0.000 claims description 4
- UJQIXEYIQCDDAB-UHFFFAOYSA-N 2-[4-[3-(2-cyclopropylphenyl)-2,7,12-triazatricyclo[6.4.0.02,6]dodeca-1(8),6,9,11-tetraen-11-yl]phenyl]propan-2-ol Chemical compound C1(CC1)C1=C(C=CC=C1)C1CCC2=NC=3C(=NC(=CC=3)C3=CC=C(C=C3)C(C)(C)O)N21 UJQIXEYIQCDDAB-UHFFFAOYSA-N 0.000 claims description 4
- DCQCGNMFCGZMGL-UHFFFAOYSA-N 2-[4-[3-(2-cyclopropylphenyl)-5-fluoro-2,7,12-triazatricyclo[6.4.0.02,6]dodeca-1(8),6,9,11-tetraen-11-yl]phenyl]propan-2-ol Chemical compound C1(CC1)C1=C(C=CC=C1)C1CC(C2=NC=3C(=NC(=CC=3)C3=CC=C(C=C3)C(C)(C)O)N21)F DCQCGNMFCGZMGL-UHFFFAOYSA-N 0.000 claims description 4
- BVWMDSRUMHZQQY-UHFFFAOYSA-N 2-[4-[3-(2-methoxyphenyl)-2,7,12-triazatricyclo[6.4.0.02,6]dodeca-1(8),6,9,11-tetraen-11-yl]phenyl]propan-2-ol Chemical compound COC1=C(C=CC=C1)C1CCC2=NC=3C(=NC(=CC=3)C3=CC=C(C=C3)C(C)(C)O)N21 BVWMDSRUMHZQQY-UHFFFAOYSA-N 0.000 claims description 4
- LWOODTYOEVZSQK-UHFFFAOYSA-N 2-[4-[3-[2-fluoro-6-(trifluoromethyl)phenyl]-2,7,12-triazatricyclo[6.4.0.02,6]dodeca-1(8),6,9,11-tetraen-11-yl]phenyl]propan-2-ol Chemical compound FC1=C(C(=CC=C1)C(F)(F)F)C1CCC2=NC=3C(=NC(=CC=3)C3=CC=C(C=C3)C(C)(C)O)N21 LWOODTYOEVZSQK-UHFFFAOYSA-N 0.000 claims description 4
- DVPPBWSHROBBFJ-UHFFFAOYSA-N 2-[4-[3-[5-fluoro-2-(trifluoromethyl)phenyl]-2,7,12-triazatricyclo[6.4.0.02,6]dodeca-1(8),6,9,11-tetraen-11-yl]phenyl]propan-2-ol Chemical compound FC=1C=CC(=C(C=1)C1CCC2=NC=3C(=NC(=CC=3)C3=CC=C(C=C3)C(C)(C)O)N21)C(F)(F)F DVPPBWSHROBBFJ-UHFFFAOYSA-N 0.000 claims description 4
- MQHNRCXLKUUPKQ-UHFFFAOYSA-N 2-[4-[5-fluoro-3-[2-(trifluoromethoxy)phenyl]-2,7,12-triazatricyclo[6.4.0.02,6]dodeca-1(8),6,9,11-tetraen-11-yl]phenyl]propan-2-ol Chemical compound FC1CC(N2C1=NC=1C2=NC(=CC=1)C1=CC=C(C=C1)C(C)(C)O)C1=C(C=CC=C1)OC(F)(F)F MQHNRCXLKUUPKQ-UHFFFAOYSA-N 0.000 claims description 4
- XEPMXXAHTTXNFI-UHFFFAOYSA-N 2-[5-[3-[2-(difluoromethoxy)phenyl]-2,7,12-triazatricyclo[6.4.0.02,6]dodeca-1(8),6,9,11-tetraen-11-yl]pyrimidin-2-yl]propan-2-ol Chemical compound FC(OC1=C(C=CC=C1)C1CCC2=NC=3C(=NC(=CC=3)C=3C=NC(=NC=3)C(C)(C)O)N21)F XEPMXXAHTTXNFI-UHFFFAOYSA-N 0.000 claims description 4
- RLIVIHIZSSNDJL-UHFFFAOYSA-N 3-(2,5-dimethylphenyl)-11-(2-morpholin-4-ylpyrimidin-5-yl)-2,7,12-triazatricyclo[6.4.0.02,6]dodeca-1(8),6,9,11-tetraen-5-ol Chemical compound CC1=C(C=C(C=C1)C)C1CC(C2=NC=3C(=NC(=CC=3)C=3C=NC(=NC=3)N3CCOCC3)N21)O RLIVIHIZSSNDJL-UHFFFAOYSA-N 0.000 claims description 4
- JIZHFNUDERURSW-UHFFFAOYSA-N 3-[2-(difluoromethoxy)phenyl]-11-[2-(2-hydroxypropan-2-yl)pyrimidin-5-yl]-2,7,12-triazatricyclo[6.4.0.02,6]dodeca-1(8),6,9,11-tetraen-5-ol Chemical compound FC(OC1=C(C=CC=C1)C1CC(C2=NC=3C(=NC(=CC=3)C=3C=NC(=NC=3)C(C)(C)O)N21)O)F JIZHFNUDERURSW-UHFFFAOYSA-N 0.000 claims description 4
- BJWVVLZXFOJPSL-UHFFFAOYSA-N 3-[5-fluoro-2-(trifluoromethyl)phenyl]-11-[4-(2-hydroxypropan-2-yl)phenyl]-2,7,12-triazatricyclo[6.4.0.02,6]dodeca-1(8),6,9,11-tetraen-5-ol Chemical compound FC=1C=CC(=C(C=1)C1CC(C2=NC=3C(=NC(=CC=3)C3=CC=C(C=C3)C(C)(C)O)N21)O)C(F)(F)F BJWVVLZXFOJPSL-UHFFFAOYSA-N 0.000 claims description 4
- GALYFDYKAMGDGH-UHFFFAOYSA-N 4-[5-[3-[2-(difluoromethoxy)phenyl]-2,7,12-triazatricyclo[6.4.0.02,6]dodeca-1(8),6,9,11-tetraen-11-yl]pyrimidin-2-yl]morpholine Chemical compound FC(OC1=C(C=CC=C1)C1CCC2=NC=3C(=NC(=CC=3)C=3C=NC(=NC=3)N3CCOCC3)N21)F GALYFDYKAMGDGH-UHFFFAOYSA-N 0.000 claims description 4
- IZIRWECBBGQVIA-UHFFFAOYSA-N 4-[5-[3-[2-(difluoromethoxy)phenyl]-5-fluoro-2,7,12-triazatricyclo[6.4.0.02,6]dodeca-1(8),6,9,11-tetraen-11-yl]pyrimidin-2-yl]morpholine Chemical compound FC(OC1=C(C=CC=C1)C1CC(C2=NC=3C(=NC(=CC=3)C=3C=NC(=NC=3)N3CCOCC3)N21)F)F IZIRWECBBGQVIA-UHFFFAOYSA-N 0.000 claims description 4
- 201000005569 Gout Diseases 0.000 claims description 4
- 201000004681 Psoriasis Diseases 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 230000000366 juvenile effect Effects 0.000 claims description 4
- 201000006417 multiple sclerosis Diseases 0.000 claims description 4
- JBBNVIMXSSPSFU-UHFFFAOYSA-N 11-[4-(2-hydroxypropan-2-yl)phenyl]-3-[2-methyl-5-(trifluoromethyl)phenyl]-2,7,12-triazatricyclo[6.4.0.02,6]dodeca-1(8),6,9,11-tetraen-5-ol Chemical compound OC(C)(C)C1=CC=C(C=C1)C1=CC=C2C(=N1)N1C(=N2)C(CC1C1=C(C=CC(=C1)C(F)(F)F)C)O JBBNVIMXSSPSFU-UHFFFAOYSA-N 0.000 claims description 3
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 3
- QDVQZQUSEZFJCL-HXUWFJFHSA-N CC1=C(C=C(C=C1)C)[C@H]1CCC2=NC=3C(=NC(=CC=3)C=3C=NC(=NC=3)C(C)(C)O)N21 Chemical compound CC1=C(C=C(C=C1)C)[C@H]1CCC2=NC=3C(=NC(=CC=3)C=3C=NC(=NC=3)C(C)(C)O)N21 QDVQZQUSEZFJCL-HXUWFJFHSA-N 0.000 claims description 3
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 3
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 3
- 208000011231 Crohn disease Diseases 0.000 claims description 3
- 206010016207 Familial Mediterranean fever Diseases 0.000 claims description 3
- 208000003807 Graves Disease Diseases 0.000 claims description 3
- 208000015023 Graves' disease Diseases 0.000 claims description 3
- 208000005777 Lupus Nephritis Diseases 0.000 claims description 3
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims description 3
- 108060008683 Tumor Necrosis Factor Receptor Proteins 0.000 claims description 3
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 3
- 208000006673 asthma Diseases 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 3
- 230000000737 periodic effect Effects 0.000 claims description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
- 208000011580 syndromic disease Diseases 0.000 claims description 3
- 230000009885 systemic effect Effects 0.000 claims description 3
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 3
- 102000003298 tumor necrosis factor receptor Human genes 0.000 claims description 3
- PSRKUYMWFFZUMV-LJQANCHMSA-N (3R)-3-(2,5-dimethylphenyl)-11-(1-methylpyrazol-4-yl)-2,7,12-triazatricyclo[6.4.0.02,6]dodeca-1(8),6,9,11-tetraene Chemical compound CC1=C(C=C(C=C1)C)[C@H]1CCC2=NC=3C(=NC(=CC=3)C=3C=NN(C=3)C)N21 PSRKUYMWFFZUMV-LJQANCHMSA-N 0.000 claims description 2
- HTWJGCUKEIUWNB-UHFFFAOYSA-N 2-[4-[3-[2-(difluoromethoxy)phenyl]-2,7,12-triazatricyclo[6.4.0.02,6]dodeca-1(8),6,9,11-tetraen-11-yl]phenyl]propan-2-ol Chemical compound FC(OC1=C(C=CC=C1)C1CCC2=NC=3C(=NC(=CC=3)C3=CC=C(C=C3)C(C)(C)O)N21)F HTWJGCUKEIUWNB-UHFFFAOYSA-N 0.000 claims description 2
- FXWYBCDCDHAQFS-UHFFFAOYSA-N 2-[4-[3-[2-(difluoromethoxy)phenyl]-5-fluoro-2,7,12-triazatricyclo[6.4.0.02,6]dodeca-1(8),6,9,11-tetraen-11-yl]phenyl]propan-2-ol Chemical compound FC(OC1=C(C=CC=C1)C1CC(C2=NC=3C(=NC(=CC=3)C3=CC=C(C=C3)C(C)(C)O)N21)F)F FXWYBCDCDHAQFS-UHFFFAOYSA-N 0.000 claims description 2
- LMLGUPLXAVIXKY-UHFFFAOYSA-N 2-[5-[3-(2,5-dimethylphenyl)-5-fluoro-2,7,12-triazatricyclo[6.4.0.02,6]dodeca-1(8),6,9,11-tetraen-11-yl]pyrimidin-2-yl]propan-2-ol Chemical compound CC1=C(C=C(C=C1)C)C1CC(C2=NC=3C(=NC(=CC=3)C=3C=NC(=NC=3)C(C)(C)O)N21)F LMLGUPLXAVIXKY-UHFFFAOYSA-N 0.000 claims description 2
- BIICWYBWGDLGDM-UHFFFAOYSA-N 2-[5-[3-[2-(difluoromethoxy)phenyl]-5-fluoro-2,7,12-triazatricyclo[6.4.0.02,6]dodeca-1(8),6,9,11-tetraen-11-yl]pyrimidin-2-yl]propan-2-ol Chemical compound FC(OC1=C(C=CC=C1)C1CC(C2=NC=3C(=NC(=CC=3)C=3C=NC(=NC=3)C(C)(C)O)N21)F)F BIICWYBWGDLGDM-UHFFFAOYSA-N 0.000 claims description 2
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 2
- 206010018634 Gouty Arthritis Diseases 0.000 claims description 2
- 208000009329 Graft vs Host Disease Diseases 0.000 claims description 2
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims description 2
- 208000024908 graft versus host disease Diseases 0.000 claims description 2
- 206010025135 lupus erythematosus Diseases 0.000 claims description 2
- 208000004296 neuralgia Diseases 0.000 claims description 2
- 208000021722 neuropathic pain Diseases 0.000 claims description 2
- 208000026326 Adult-onset Still disease Diseases 0.000 claims 1
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 3
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 abstract 5
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 235000002639 sodium chloride Nutrition 0.000 description 99
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 50
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- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 39
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 36
- 238000000034 method Methods 0.000 description 36
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 19
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- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 18
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- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 16
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- 235000019257 ammonium acetate Nutrition 0.000 description 16
- 229940043376 ammonium acetate Drugs 0.000 description 16
- 208000035475 disorder Diseases 0.000 description 16
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- 125000005842 heteroatom Chemical group 0.000 description 14
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- 239000002904 solvent Substances 0.000 description 12
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
- 239000011734 sodium Substances 0.000 description 10
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- 229910052721 tungsten Inorganic materials 0.000 description 10
- 229910052727 yttrium Inorganic materials 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/06—Peri-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Epidemiology (AREA)
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| US201562134769P | 2015-03-18 | 2015-03-18 | |
| PCT/US2016/022737 WO2016149436A1 (en) | 2015-03-18 | 2016-03-17 | Substituted tricyclic heterocyclic compounds |
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| ES2797805T3 true ES2797805T3 (es) | 2020-12-03 |
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| EP3294726A1 (en) | 2015-04-17 | 2018-03-21 | AbbVie Inc. | Indazolones as modulators of tnf signaling |
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| AU2015328414B2 (en) | 2014-10-06 | 2020-03-19 | Signal Pharmaceuticals, Llc | Substituted aminopurine compounds, compositions thereof, and methods of treatment therewith |
| WO2016149439A1 (en) | 2015-03-18 | 2016-09-22 | Bristol-Myers Squibb Company | Heterocyclic compounds useful as inhibitors of tnf |
| CA2982446A1 (en) | 2015-03-18 | 2016-09-22 | Bristol-Myers Squibb Company | Tricyclic heterocyclic compounds useful as inhibitors of tnf |
-
2016
- 2016-03-17 WO PCT/US2016/022737 patent/WO2016149436A1/en not_active Ceased
- 2016-03-17 CA CA2980159A patent/CA2980159A1/en not_active Abandoned
- 2016-03-17 ES ES16712645T patent/ES2797805T3/es active Active
- 2016-03-17 MX MX2017011434A patent/MX2017011434A/es unknown
- 2016-03-17 BR BR112017019773-1A patent/BR112017019773A2/pt not_active Application Discontinuation
- 2016-03-17 EP EP16712645.7A patent/EP3271360B1/en active Active
- 2016-03-17 AU AU2016233288A patent/AU2016233288A1/en not_active Abandoned
- 2016-03-17 KR KR1020177029449A patent/KR102654709B1/ko active Active
- 2016-03-17 US US15/558,692 patent/US10189840B2/en active Active
- 2016-03-17 CN CN201680026733.XA patent/CN107635993B/zh active Active
- 2016-03-17 EA EA201792034A patent/EA032315B1/ru not_active IP Right Cessation
- 2016-03-17 JP JP2017549092A patent/JP6793657B2/ja active Active
- 2016-03-17 SG SG11201707469WA patent/SG11201707469WA/en unknown
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2017
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Also Published As
| Publication number | Publication date |
|---|---|
| EP3271360A1 (en) | 2018-01-24 |
| IL254424A0 (en) | 2017-11-30 |
| US10189840B2 (en) | 2019-01-29 |
| JP2018508553A (ja) | 2018-03-29 |
| EA032315B1 (ru) | 2019-05-31 |
| JP6793657B2 (ja) | 2020-12-02 |
| CA2980159A1 (en) | 2016-09-22 |
| EA201792034A1 (ru) | 2018-03-30 |
| CN107635993B (zh) | 2020-05-22 |
| SG11201707469WA (en) | 2017-10-30 |
| KR102654709B1 (ko) | 2024-04-03 |
| AU2016233288A1 (en) | 2017-11-09 |
| KR20170129810A (ko) | 2017-11-27 |
| US20180111936A1 (en) | 2018-04-26 |
| EP3271360B1 (en) | 2020-04-22 |
| BR112017019773A2 (pt) | 2018-05-15 |
| CN107635993A (zh) | 2018-01-26 |
| WO2016149436A1 (en) | 2016-09-22 |
| MX2017011434A (es) | 2018-01-25 |
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