ES2730942T3 - Derivados de triazolopiridina como moduladores de la actividad de TNF - Google Patents
Derivados de triazolopiridina como moduladores de la actividad de TNF Download PDFInfo
- Publication number
- ES2730942T3 ES2730942T3 ES14808638T ES14808638T ES2730942T3 ES 2730942 T3 ES2730942 T3 ES 2730942T3 ES 14808638 T ES14808638 T ES 14808638T ES 14808638 T ES14808638 T ES 14808638T ES 2730942 T3 ES2730942 T3 ES 2730942T3
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- Prior art keywords
- methyl
- alkyl
- optionally substituted
- carboxy
- formula
- Prior art date
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- 230000000694 effects Effects 0.000 title description 8
- 150000008523 triazolopyridines Chemical class 0.000 title description 3
- -1 ethoxycarbonylethyl Chemical group 0.000 claims abstract description 995
- 150000001875 compounds Chemical class 0.000 claims abstract description 196
- 125000001424 substituent group Chemical group 0.000 claims abstract description 125
- 239000001257 hydrogen Substances 0.000 claims abstract description 99
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 99
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 77
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 72
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 69
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 59
- 150000002367 halogens Chemical class 0.000 claims abstract description 59
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 49
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 39
- 239000011737 fluorine Chemical group 0.000 claims abstract description 37
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 37
- 239000000460 chlorine Chemical group 0.000 claims abstract description 36
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 32
- 150000003839 salts Chemical class 0.000 claims abstract description 32
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 31
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 31
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 27
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims abstract description 26
- 239000012453 solvate Substances 0.000 claims abstract description 21
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims abstract description 17
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 17
- 125000002757 morpholinyl group Chemical group 0.000 claims abstract description 14
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract description 13
- 125000004193 piperazinyl group Chemical group 0.000 claims abstract description 10
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 8
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims abstract description 7
- 125000002393 azetidinyl group Chemical group 0.000 claims abstract description 6
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims abstract description 6
- 125000004622 benzoxazinyl group Chemical group O1NC(=CC2=C1C=CC=C2)* 0.000 claims abstract description 4
- 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims abstract description 4
- 125000004582 dihydrobenzothienyl group Chemical group S1C(CC2=C1C=CC=C2)* 0.000 claims abstract description 4
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims abstract description 4
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims abstract description 4
- 125000000160 oxazolidinyl group Chemical group 0.000 claims abstract description 4
- 125000004605 1,2,3,4-tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 182
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- 238000011282 treatment Methods 0.000 claims description 50
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 38
- 125000003545 alkoxy group Chemical group 0.000 claims description 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 24
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 125000003386 piperidinyl group Chemical group 0.000 claims description 16
- 208000035475 disorder Diseases 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
- 208000027866 inflammatory disease Diseases 0.000 claims description 8
- 230000001363 autoimmune Effects 0.000 claims description 7
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 7
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- 208000030159 metabolic disease Diseases 0.000 claims description 6
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 6
- 230000000926 neurological effect Effects 0.000 claims description 6
- 230000000771 oncological effect Effects 0.000 claims description 6
- 230000002265 prevention Effects 0.000 claims description 6
- 125000001984 thiazolidinyl group Chemical group 0.000 claims description 6
- 208000002193 Pain Diseases 0.000 claims description 5
- 125000003725 azepanyl group Chemical group 0.000 claims description 5
- 125000005959 diazepanyl group Chemical group 0.000 claims description 5
- 208000030533 eye disease Diseases 0.000 claims description 5
- 230000003040 nociceptive effect Effects 0.000 claims description 5
- 125000005961 oxazepanyl group Chemical group 0.000 claims description 5
- 125000003566 oxetanyl group Chemical group 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000002632 imidazolidinyl group Chemical group 0.000 claims description 3
- 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- 125000004607 1,2,3,4-tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 2
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 13
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract description 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract description 3
- 125000005310 triazolidinyl group Chemical group N1(NNCC1)* 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 description 45
- 125000004093 cyano group Chemical group *C#N 0.000 description 37
- 125000001072 heteroaryl group Chemical group 0.000 description 36
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 33
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 33
- 108700012920 TNF Proteins 0.000 description 29
- 125000003282 alkyl amino group Chemical group 0.000 description 26
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 26
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 25
- 125000004366 heterocycloalkenyl group Chemical group 0.000 description 24
- 125000000753 cycloalkyl group Chemical group 0.000 description 23
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 22
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 22
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 21
- 239000002253 acid Substances 0.000 description 21
- 239000002585 base Substances 0.000 description 21
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 21
- 239000000543 intermediate Substances 0.000 description 21
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
- 238000000034 method Methods 0.000 description 20
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 19
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 18
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 18
- 229910052794 bromium Inorganic materials 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 18
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 125000000392 cycloalkenyl group Chemical group 0.000 description 17
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 17
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 16
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 16
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 16
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 16
- 150000001602 bicycloalkyls Chemical group 0.000 description 15
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 15
- 125000001544 thienyl group Chemical group 0.000 description 15
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 15
- 125000004663 dialkyl amino group Chemical group 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 14
- 239000000651 prodrug Substances 0.000 description 14
- 229940002612 prodrug Drugs 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- 125000003831 tetrazolyl group Chemical group 0.000 description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
- 125000004076 pyridyl group Chemical group 0.000 description 13
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 12
- 239000013078 crystal Substances 0.000 description 12
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- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 11
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 125000000335 thiazolyl group Chemical group 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 10
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
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- 210000004027 cell Anatomy 0.000 description 10
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 10
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- 208000023275 Autoimmune disease Diseases 0.000 description 9
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 9
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- 125000002947 alkylene group Chemical group 0.000 description 9
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- 229910052723 transition metal Inorganic materials 0.000 description 9
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 8
- 125000001153 fluoro group Chemical group F* 0.000 description 8
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- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 7
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 6
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Classifications
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- 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
- C07D471/02—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 two hetero rings
- C07D471/04—Ortho-condensed systems
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- 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
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- Chemical & Material Sciences (AREA)
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- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
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| GBGB1321742.7A GB201321742D0 (en) | 2013-12-09 | 2013-12-09 | Therapeutic agents |
| PCT/EP2014/076832 WO2015086496A1 (en) | 2013-12-09 | 2014-12-08 | Triazolopyridine derivatives as modulators of tnf activity |
Publications (1)
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| ES2730942T3 true ES2730942T3 (es) | 2019-11-13 |
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| ES14808638T Active ES2730942T3 (es) | 2013-12-09 | 2014-12-08 | Derivados de triazolopiridina como moduladores de la actividad de TNF |
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| EP (1) | EP3080109B1 (enExample) |
| JP (1) | JP6426185B2 (enExample) |
| CN (1) | CN105814043B (enExample) |
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| RU (1) | RU2677697C1 (enExample) |
| TR (1) | TR201907702T4 (enExample) |
| WO (1) | WO2015086496A1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
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| GB201321735D0 (en) * | 2013-12-09 | 2014-01-22 | Ucb Pharma Sa | Therapeutic Agents |
| ES2797685T3 (es) | 2015-03-18 | 2020-12-03 | Bristol Myers Squibb Co | Compuestos heterocíclicos tricíclicos útiles como inhibidores de TNF |
| KR102696304B1 (ko) | 2015-03-18 | 2024-08-16 | 브리스톨-마이어스 스큅 컴퍼니 | Tnf의 억제제로서 유용한 헤테로시클릭 화합물 |
| EA032315B1 (ru) | 2015-03-18 | 2019-05-31 | Бристол-Маерс Сквибб Компани | Замещенные трициклические гетероциклические соединения |
| AR104293A1 (es) | 2015-04-17 | 2017-07-12 | Abbvie Inc | Indazolonas como moduladores de la señalización de tnf |
| US9856253B2 (en) | 2015-04-17 | 2018-01-02 | Abbvie, Inc. | Tricyclic modulators of TNF signaling |
| US20160304496A1 (en) | 2015-04-17 | 2016-10-20 | Abbvie Inc. | Indazolones as modulators of tnf signaling |
| GB201510758D0 (en) | 2015-06-18 | 2015-08-05 | Ucb Biopharma Sprl | Novel TNFa structure for use in therapy |
| CN108137609B (zh) | 2015-08-03 | 2021-07-16 | 百时美施贵宝公司 | 用作TNFα的调节剂的环状化合物 |
| EP4467565A3 (en) | 2016-12-21 | 2025-03-12 | Amgen Inc. | Anti-tnf alpha antibody formulations |
| GB201621907D0 (en) | 2016-12-21 | 2017-02-01 | Ucb Biopharma Sprl And Sanofi | Antibody epitope |
| WO2019192533A1 (zh) * | 2018-04-04 | 2019-10-10 | 深圳福沃药业有限公司 | 用于治疗乳腺癌的雌激素受体降解剂 |
Family Cites Families (29)
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| FR2601952B1 (fr) * | 1986-07-23 | 1988-11-25 | Carpibem | Nouveaux derives amino alkyl thio de triazolopyridine ou triazoloquinoline, leurs procedes de preparation, medicaments les contenant, utiles notamment comme antalgiques |
| DE10038019A1 (de) * | 2000-08-04 | 2002-02-14 | Bayer Ag | Substituierte Triazolopyrid(az)ine |
| KR20030080087A (ko) * | 2001-03-09 | 2003-10-10 | 화이자 프로덕츠 인코포레이티드 | 항염증제로서의 트리아졸로피리딘 |
| CN2783538Y (zh) | 2004-08-04 | 2006-05-24 | 蒋沛康 | 无电线电池按扣 |
| EP1786811A2 (en) * | 2004-08-18 | 2007-05-23 | Pharmacia & Upjohn Company LLC | Triazolopyridine compounds |
| US7572807B2 (en) * | 2005-06-09 | 2009-08-11 | Bristol-Myers Squibb Company | Heteroaryl 11-beta-hydroxysteroid dehydrogenase type I inhibitors |
| US7579360B2 (en) | 2005-06-09 | 2009-08-25 | Bristol-Myers Squibb Company | Triazolopyridine 11-beta hydroxysteroid dehydrogenase type I inhibitors |
| PE20121506A1 (es) * | 2006-07-14 | 2012-11-26 | Amgen Inc | Compuestos triazolopiridinas como inhibidores de c-met |
| US8217177B2 (en) * | 2006-07-14 | 2012-07-10 | Amgen Inc. | Fused heterocyclic derivatives and methods of use |
| US7700593B2 (en) * | 2006-10-11 | 2010-04-20 | Amgen Inc. | Imidazo- and triazolo-pyridine compounds and methods of use thereof |
| US8119658B2 (en) * | 2007-10-01 | 2012-02-21 | Bristol-Myers Squibb Company | Triazolopyridine 11-beta hydroxysteroid dehydrogenase type I inhibitors |
| US8324241B2 (en) * | 2008-04-11 | 2012-12-04 | Bristol-Myers Squibb Company | Triazolo compounds useful as DGAT1 inhibitors |
| FR2933980B1 (fr) * | 2008-07-18 | 2011-07-29 | Sanofi Aventis | Nouveaux derives triazolo°4,3-a!pyridine, leur procede de preparation, leur application a titre de medicaments, compositions pharmaceutiques et nouvelle utilisation notamment comme inhibiteurs de met |
| AU2009272516A1 (en) * | 2008-07-18 | 2010-01-21 | Sanofi-Aventis | Novel triazolo(4,3-a)pyridine derivatives, process for the preparation thereof, use thereof as medicaments, pharmaceutical compositions and novel use, in particular as MET inhibitors |
| WO2010022081A1 (en) * | 2008-08-19 | 2010-02-25 | Array Biopharma Inc. | Triazolopyridine compounds as pim kinase inhibitors |
| TWI496779B (zh) * | 2008-08-19 | 2015-08-21 | Array Biopharma Inc | 作為ｐｉｍ激酶抑制劑之三唑吡啶化合物 |
| DE102008063667A1 (de) * | 2008-12-18 | 2010-07-01 | Merck Patent Gmbh | 3-(3-Pyrimidin-2-yl-benzyl)-°[1,2,4]triazolo[4,3-b]pyrimidin-derivate |
| CN102395586A (zh) * | 2009-02-17 | 2012-03-28 | 奇斯药制品公司 | 作为p38map激酶抑制剂的三唑并吡啶衍生物 |
| SMT201700456T1 (it) * | 2009-07-27 | 2017-11-15 | Gilead Sciences Inc | Composti eterociclici fusi come modulatori dei canali ionici |
| FR2966471A1 (fr) * | 2010-09-20 | 2012-04-27 | Valeo Vision | Piece de vehicule automobile en materiau a base de polymere (s) traite en surface |
| WO2012065297A1 (en) * | 2010-11-16 | 2012-05-24 | Impact Therapeutics, Inc. | 3-ARYL-6-ARYL-[1,2,4]TRIAZOLO[4,3-a]PYRIDINES AS INHIBITORS OF CELL PROLIFERATION AND THE USE THEREOF |
| EP2755976B1 (en) * | 2011-09-15 | 2018-07-18 | Novartis AG | 6-substituted 3-(quinolin-6-ylthio)-[1,2,4]triazolo[4,3-a]pyridines as c-met tyrosine kinase inhibitors |
| CN103130792B (zh) * | 2011-11-30 | 2016-05-04 | 正大天晴药业集团股份有限公司 | 一种2-氨基噻唑类化合物 |
| CA2858420A1 (en) * | 2011-12-09 | 2013-06-13 | Chiesi Farmaceutici S.P.A. | Derivatives of 4-hydroxy-1,2,3,4-tetrahydronaphthalen-1-yl urea and their use in the treatment of, inter alia, diseases of the respiratory tract |
| US9340549B2 (en) * | 2012-03-05 | 2016-05-17 | Amgen Inc. | Oxazolidinone compounds and derivatives thereof |
| US8765767B2 (en) | 2012-03-16 | 2014-07-01 | Bristol-Myers Squibb Company | Positive allosteric modulators of mGluR2 |
| TR201807207T4 (tr) | 2012-06-11 | 2018-06-21 | Ucb Biopharma Sprl | Tnf-alfa modüle edici benzimidazol bileşikleri. |
| GB201212513D0 (en) | 2012-07-13 | 2012-08-29 | Ucb Pharma Sa | Therapeutic agents |
| CN104619709B (zh) | 2012-07-13 | 2016-11-09 | Ucb生物制药私人有限公司 | 作为tnf活性调节剂的咪唑并吡啶衍生物 |
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| EP3080109B1 (en) | 2019-05-15 |
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| US20160304512A1 (en) | 2016-10-20 |
| US9850240B2 (en) | 2017-12-26 |
| TR201907702T4 (tr) | 2019-06-21 |
| CA2931578A1 (en) | 2015-06-18 |
| CN105814043A (zh) | 2016-07-27 |
| CN105814043B (zh) | 2019-05-17 |
| RU2016127228A (ru) | 2018-01-23 |
| BR112016011844B1 (pt) | 2022-08-16 |
| JP2016539971A (ja) | 2016-12-22 |
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