CA2703037A1 - Organic compounds - Google Patents
Organic compounds Download PDFInfo
- Publication number
- CA2703037A1 CA2703037A1 CA2703037A CA2703037A CA2703037A1 CA 2703037 A1 CA2703037 A1 CA 2703037A1 CA 2703037 A CA2703037 A CA 2703037A CA 2703037 A CA2703037 A CA 2703037A CA 2703037 A1 CA2703037 A1 CA 2703037A1
- Authority
- CA
- Canada
- Prior art keywords
- pyridin
- imidazo
- alkyl
- phenyl
- pyridine
- 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.)
- Abandoned
Links
- 150000002894 organic compounds Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 174
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 33
- 238000011282 treatment Methods 0.000 claims abstract description 28
- 201000010099 disease Diseases 0.000 claims abstract description 21
- 208000002815 pulmonary hypertension Diseases 0.000 claims abstract description 21
- 208000005069 pulmonary fibrosis Diseases 0.000 claims abstract description 19
- 208000019425 cirrhosis of liver Diseases 0.000 claims abstract description 15
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 13
- 102100034134 Activin receptor type-1B Human genes 0.000 claims abstract description 12
- 208000001132 Osteoporosis Diseases 0.000 claims abstract description 9
- 201000011510 cancer Diseases 0.000 claims abstract description 9
- 230000001404 mediated effect Effects 0.000 claims abstract description 9
- 101710173011 Activin receptor type-1B Proteins 0.000 claims abstract description 8
- 101000712674 Homo sapiens TGF-beta receptor type-1 Proteins 0.000 claims abstract description 8
- 102100033456 TGF-beta receptor type-1 Human genes 0.000 claims abstract description 8
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- 208000029578 Muscle disease Diseases 0.000 claims abstract description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 61
- -1 C(O)NR5R6 Chemical group 0.000 claims description 60
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 39
- 125000000623 heterocyclic group Chemical group 0.000 claims description 30
- 125000005843 halogen group Chemical group 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 150000002367 halogens Chemical class 0.000 claims description 20
- 230000005764 inhibitory process Effects 0.000 claims description 18
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 17
- 210000000988 bone and bone Anatomy 0.000 claims description 17
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 17
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 14
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 14
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 10
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 201000001320 Atherosclerosis Diseases 0.000 claims description 6
- 230000001154 acute effect Effects 0.000 claims description 6
- 150000008064 anhydrides Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 208000017169 kidney disease Diseases 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 150000003462 sulfoxides Chemical class 0.000 claims description 6
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 6
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 5
- 239000011575 calcium Substances 0.000 claims description 5
- 229910052791 calcium Inorganic materials 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 208000037803 restenosis Diseases 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 5
- 230000029663 wound healing Effects 0.000 claims description 5
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
- 206010006956 Calcium deficiency Diseases 0.000 claims description 4
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims description 4
- 208000025865 Ulcer Diseases 0.000 claims description 4
- 208000027418 Wounds and injury Diseases 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 208000020832 chronic kidney disease Diseases 0.000 claims description 4
- 208000033679 diabetic kidney disease Diseases 0.000 claims description 4
- 230000011164 ossification Effects 0.000 claims description 4
- 230000037390 scarring Effects 0.000 claims description 4
- 230000000638 stimulation Effects 0.000 claims description 4
- 231100000397 ulcer Toxicity 0.000 claims description 4
- 208000024827 Alzheimer disease Diseases 0.000 claims description 3
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- 206010019280 Heart failures Diseases 0.000 claims description 3
- 206010023421 Kidney fibrosis Diseases 0.000 claims description 3
- 206010052428 Wound Diseases 0.000 claims description 3
- 206010003246 arthritis Diseases 0.000 claims description 3
- 208000006454 hepatitis Diseases 0.000 claims description 3
- 231100000283 hepatitis Toxicity 0.000 claims description 3
- 230000001771 impaired effect Effects 0.000 claims description 3
- 230000007658 neurological function Effects 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- 101100173726 Arabidopsis thaliana OR23 gene Proteins 0.000 claims description 2
- 208000008439 Biliary Liver Cirrhosis Diseases 0.000 claims description 2
- 208000033222 Biliary cirrhosis primary Diseases 0.000 claims description 2
- 201000009273 Endometriosis Diseases 0.000 claims description 2
- 208000018565 Hemochromatosis Diseases 0.000 claims description 2
- 208000014919 IgG4-related retroperitoneal fibrosis Diseases 0.000 claims description 2
- 208000002260 Keloid Diseases 0.000 claims description 2
- 206010027398 Mesenteric fibrosis Diseases 0.000 claims description 2
- 208000022873 Ocular disease Diseases 0.000 claims description 2
- 208000012654 Primary biliary cholangitis Diseases 0.000 claims description 2
- 206010038979 Retroperitoneal fibrosis Diseases 0.000 claims description 2
- 230000002159 abnormal effect Effects 0.000 claims description 2
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 230000004221 bone function Effects 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 2
- 208000002672 hepatitis B Diseases 0.000 claims description 2
- 210000001117 keloid Anatomy 0.000 claims description 2
- 229940124530 sulfonamide Drugs 0.000 claims description 2
- 150000003456 sulfonamides Chemical class 0.000 claims description 2
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 208000005176 Hepatitis C Diseases 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 65
- 108020003175 receptors Proteins 0.000 abstract description 27
- 150000003839 salts Chemical group 0.000 abstract description 24
- 208000035475 disorder Diseases 0.000 abstract description 12
- 230000002757 inflammatory effect Effects 0.000 abstract description 11
- 239000012453 solvate Chemical group 0.000 abstract description 11
- 210000003205 muscle Anatomy 0.000 abstract description 8
- 208000027771 Obstructive airways disease Diseases 0.000 abstract description 7
- 201000000585 muscular atrophy Diseases 0.000 abstract description 7
- 230000008569 process Effects 0.000 abstract description 5
- 230000020763 muscle atrophy Effects 0.000 abstract description 4
- 230000009885 systemic effect Effects 0.000 abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 186
- 239000000543 intermediate Substances 0.000 description 120
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 107
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 79
- 239000011541 reaction mixture Substances 0.000 description 74
- 229910001868 water Inorganic materials 0.000 description 53
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 52
- 235000019439 ethyl acetate Nutrition 0.000 description 51
- 239000000203 mixture Substances 0.000 description 44
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 43
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 43
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 42
- 239000007787 solid Substances 0.000 description 41
- 238000003818 flash chromatography Methods 0.000 description 35
- 239000002904 solvent Substances 0.000 description 35
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 34
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 34
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- 238000006243 chemical reaction Methods 0.000 description 29
- 239000000243 solution Substances 0.000 description 28
- 102000005962 receptors Human genes 0.000 description 26
- 229910000029 sodium carbonate Inorganic materials 0.000 description 26
- 235000017550 sodium carbonate Nutrition 0.000 description 26
- 239000012267 brine Substances 0.000 description 25
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 25
- 239000012298 atmosphere Substances 0.000 description 24
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 22
- 229910052786 argon Inorganic materials 0.000 description 22
- 239000000377 silicon dioxide Substances 0.000 description 21
- 239000003795 chemical substances by application Substances 0.000 description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
- 230000005855 radiation Effects 0.000 description 19
- 239000003814 drug Substances 0.000 description 18
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 17
- 235000019341 magnesium sulphate Nutrition 0.000 description 17
- 235000017557 sodium bicarbonate Nutrition 0.000 description 17
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 17
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 16
- CYEFKCRAAGLNHW-UHFFFAOYSA-N furan-3-ylboronic acid Chemical compound OB(O)C=1C=COC=1 CYEFKCRAAGLNHW-UHFFFAOYSA-N 0.000 description 15
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
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- QJPQVXSHYBGQGM-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 QJPQVXSHYBGQGM-UHFFFAOYSA-N 0.000 description 12
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 11
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 11
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- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 10
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- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 5
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- WJYRVVDXJMJLTN-UHFFFAOYSA-N (2-chloropyridin-4-yl)boronic acid Chemical compound OB(O)C1=CC=NC(Cl)=C1 WJYRVVDXJMJLTN-UHFFFAOYSA-N 0.000 description 4
- HGMHJUKRKRGBRP-UHFFFAOYSA-N 1-[(3-bromoimidazo[1,2-a]pyridin-6-yl)amino]cyclohexan-1-ol Chemical compound C1=CC2=NC=C(Br)N2C=C1NC1(O)CCCCC1 HGMHJUKRKRGBRP-UHFFFAOYSA-N 0.000 description 4
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Landscapes
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Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
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| EP07118726.4 | 2007-10-17 | ||
| EP07118726 | 2007-10-17 | ||
| EP08151336.8 | 2008-02-12 | ||
| EP08151336 | 2008-02-12 | ||
| PCT/EP2008/063841 WO2009050183A2 (en) | 2007-10-17 | 2008-10-15 | Imidazo [1, 2-a] pyridine derivatives useful as alk inhibitors |
Publications (1)
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| CA2703037A1 true CA2703037A1 (en) | 2009-04-23 |
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| CA2703037A Abandoned CA2703037A1 (en) | 2007-10-17 | 2008-10-15 | Organic compounds |
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| US8343966B2 (en) * | 2008-01-11 | 2013-01-01 | Novartis Ag | Organic compounds |
| CN102159559A (zh) * | 2008-07-18 | 2011-08-17 | 赛诺菲-安万特 | 新型咪唑并[1,2-a]吡啶衍生物、其制备方法、其作为药物的用途、其药物组合物和新型用途特别是作为MET抑制剂的新型用途 |
| FR2945806B1 (fr) * | 2009-05-19 | 2013-04-05 | Sanofi Aventis | Nouveaux derives imidazo[1,2-a]pyridine,procede de preparation,medicaments,compositions pharmaceutiques et utilisation notamment comme inhibiteurs de met |
| CA2760778A1 (en) * | 2009-05-13 | 2010-11-18 | Amgen Inc. | Heteroaryl compounds as pikk inhibitors |
| EP2454262B1 (en) * | 2009-07-15 | 2014-05-14 | Abbott Laboratories | Pyrrolopyrazine inhibitors of kinases |
| UY33213A (es) | 2010-02-18 | 2011-09-30 | Almirall Sa | Derivados de pirazol como inhibidores de jak |
| WO2011146287A1 (en) | 2010-05-20 | 2011-11-24 | Takeda Pharmaceutical Company Limited | Pyrazolo[4,3-b]pyridine-7-amine inhibitors of alk5 |
| CN102443009B (zh) * | 2010-09-30 | 2014-04-16 | 山东轩竹医药科技有限公司 | 并环激酶抑制剂 |
| EP2463289A1 (en) | 2010-11-26 | 2012-06-13 | Almirall, S.A. | Imidazo[1,2-b]pyridazine derivatives as JAK inhibitors |
| PH12013502695A1 (en) * | 2011-07-01 | 2019-06-14 | Bayer Ip Gmbh | Hydroxymethylaryl-substituted pyrrolotriazines as alk1 inhibitors |
| EP2554544A1 (en) | 2011-08-01 | 2013-02-06 | Almirall, S.A. | Pyridin-2(1h)-one derivatives as jak inhibitors |
| ES2790358T3 (es) | 2011-12-28 | 2020-10-27 | Global Blood Therapeutics Inc | Compuestos de heteroaril aldehído sustituido y métodos para su uso en el aumento de la oxigenación tisular |
| SI3738434T1 (sl) * | 2011-12-28 | 2024-01-31 | Global Blood Therapeutics, Inc. | Vmesne spojine za pridobivanje substituiranih benzaldehidnih spojin in postopki njihove uporabe pri povečanju oksigenacije tkiv |
| GB201205669D0 (en) * | 2012-03-30 | 2012-05-16 | Agency Science Tech & Res | Bicyclic heterocyclic derivatives as mnk2 and mnk2 modulators and uses thereof |
| US10280168B2 (en) | 2012-03-30 | 2019-05-07 | Agency For Science, Technology And Research | Bicyclic heteroaryl derivatives as MNK1 and MNK2 modulators and uses thereof |
| BR112014030812B1 (pt) | 2012-06-13 | 2022-11-08 | Incyte Holdings Corporation | Compostos tricíclicos substituídos como inibidores de fgfr, seus usos, composição farmacêutica e método para inibir uma enzima fgfr |
| US9738636B2 (en) | 2012-09-28 | 2017-08-22 | Vanderbilt University | Fused heterocyclic compounds as selective BMP inhibitors |
| US9981939B2 (en) | 2013-03-15 | 2018-05-29 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| EP2970196B1 (en) | 2013-03-15 | 2020-11-25 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
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| US10100043B2 (en) | 2013-03-15 | 2018-10-16 | Global Blood Therapeutics, Inc. | Substituted aldehyde compounds and methods for their use in increasing tissue oxygenation |
| US9802900B2 (en) | 2013-03-15 | 2017-10-31 | Global Blood Therapeutics, Inc. | Bicyclic heteroaryl compounds and uses thereof for the modulation of hemoglobin |
| US8952171B2 (en) | 2013-03-15 | 2015-02-10 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| SG11201507453VA (en) | 2013-03-15 | 2015-10-29 | Global Blood Therapeutics Inc | Compounds and uses thereof for the modulation of hemoglobin |
| US10266551B2 (en) | 2013-03-15 | 2019-04-23 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| US20140274961A1 (en) | 2013-03-15 | 2014-09-18 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| US9458139B2 (en) | 2013-03-15 | 2016-10-04 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| US9604999B2 (en) | 2013-03-15 | 2017-03-28 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| ME03015B (me) | 2013-04-19 | 2018-10-20 | Incyte Holdings Corp | Biciklični heterocikli kao fgfr inhibitori |
| WO2015031285A1 (en) * | 2013-08-27 | 2015-03-05 | Global Blood Therapeutics, Inc. | Crystalline 2-hydroxy-6-((2-(1-isopropyl-1h-pyrazol-5-yl)pyridin-3-yl)methoxy)benzaldehyde ansolvate salts |
| EA201992707A1 (ru) | 2013-11-18 | 2020-06-30 | Глобал Блад Терапьютикс, Инк. | Соединения и их применения для модуляции гемоглобина |
| DK3102208T4 (da) | 2014-02-07 | 2024-08-26 | Global Blood Therapeutics Inc | Krystallinsk polymorph af den frie base af 2-hydroxy-6-((2-(1-isopropyl-1H-pyrazol-5-yl)pyridin-3-yl)methoxy)benzaldehyd |
| MA41551A (fr) | 2015-02-20 | 2017-12-26 | Incyte Corp | Hétérocycles bicycliques utilisés en tant qu'inhibiteurs de fgfr4 |
| MA41841A (fr) | 2015-03-30 | 2018-02-06 | Global Blood Therapeutics Inc | Composés aldéhyde pour le traitement de la fibrose pulmonaire, de l'hypoxie, et de maladies auto-immunes et des tissus conjonctifs |
| US10836742B2 (en) | 2015-08-11 | 2020-11-17 | Neomed Institute | N-substituted bicyclic lactams, their preparation and their use as pharmaceuticals |
| US10501438B2 (en) | 2015-08-11 | 2019-12-10 | Neomed Institute | Aryl-substituted dihydroquinolinones, their preparation and their use as pharmaceuticals |
| ES2904258T3 (es) | 2015-08-12 | 2022-04-04 | Neomed Inst | Bencimidazoles sustituidos, su preparación y su uso como productos farmacéuticos |
| WO2017066876A1 (en) | 2015-10-21 | 2017-04-27 | Neomed Institute | Substituted imidazopyridines, their preparation and their use as pharmaceuticals |
| ES3039236T3 (en) | 2015-12-04 | 2025-10-20 | Global Blood Therapeutics Inc | Dosing regimens for 2-hydroxy-6-((2-(1-isopropyl-1h-pyrazol-5-yl)pyridin-3-yl)methoxy)benzaldehyde |
| US10519151B2 (en) | 2016-01-28 | 2019-12-31 | Neomed Institute | Substituted [1,2,4]triazolo[4,3-A]pyridines, their preparation and their use as pharmaceuticals |
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| US11352328B2 (en) | 2016-07-12 | 2022-06-07 | Arisan Therapeutics Inc. | Heterocyclic compounds for the treatment of arenavirus |
| WO2018053126A1 (en) * | 2016-09-14 | 2018-03-22 | Vanderbilt University | Inhibition of bmp signaling, compounds, compositions and uses thereof |
| TW202332423A (zh) | 2016-10-12 | 2023-08-16 | 美商全球血液治療公司 | 包含2-羥基-6-((2-(1-異丙基-1h-吡唑-5-基)吡啶-3-基)甲氧基)-苯甲醛之片劑 |
| AR111960A1 (es) | 2017-05-26 | 2019-09-04 | Incyte Corp | Formas cristalinas de un inhibidor de fgfr y procesos para su preparación |
| KR20200115620A (ko) | 2018-01-29 | 2020-10-07 | 메르크 파텐트 게엠베하 | Gcn2 억제제 및 이의 용도 |
| EP3765460A1 (en) | 2018-03-14 | 2021-01-20 | Vanderbilt University | Inhibition of bmp signaling, compounds, compositions and uses thereof |
| TW201946630A (zh) | 2018-05-04 | 2019-12-16 | 美商英塞特公司 | Fgfr抑制劑之鹽 |
| SG11202010636VA (en) | 2018-05-04 | 2020-11-27 | Incyte Corp | Solid forms of an fgfr inhibitor and processes for preparing the same |
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| US11591329B2 (en) | 2019-07-09 | 2023-02-28 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| JP7300057B2 (ja) * | 2019-07-26 | 2023-06-28 | シージーンテック （スーチョウ， チャイナ） カンパニー リミテッド | Ｆｇｆｒとｖｅｇｆｒ二重阻害剤としてのピリジン誘導体 |
| US12122767B2 (en) | 2019-10-01 | 2024-10-22 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
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| WO2021076728A1 (en) | 2019-10-16 | 2021-04-22 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
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| CN111116582B (zh) * | 2019-12-18 | 2022-07-29 | 大连大学 | 一种mGluR2拮抗剂 |
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2008
- 2008-10-15 KR KR1020107010615A patent/KR20100076022A/ko not_active Withdrawn
- 2008-10-15 BR BRPI0817434-2A patent/BRPI0817434A2/pt not_active IP Right Cessation
- 2008-10-15 EP EP08838625A patent/EP2212323B1/en active Active
- 2008-10-15 AR ARP080104492A patent/AR068877A1/es unknown
- 2008-10-15 EA EA201000615A patent/EA201000615A1/ru unknown
- 2008-10-15 PL PL08838625T patent/PL2212323T3/pl unknown
- 2008-10-15 US US12/679,549 patent/US8367662B2/en not_active Expired - Fee Related
- 2008-10-15 PE PE2008001769A patent/PE20091383A1/es not_active Application Discontinuation
- 2008-10-15 MX MX2010004244A patent/MX2010004244A/es active IP Right Grant
- 2008-10-15 JP JP2010529359A patent/JP5456681B2/ja not_active Expired - Fee Related
- 2008-10-15 CN CN2008801122032A patent/CN101827844B/zh not_active Expired - Fee Related
- 2008-10-15 WO PCT/EP2008/063841 patent/WO2009050183A2/en not_active Ceased
- 2008-10-15 ES ES08838625T patent/ES2393430T3/es active Active
- 2008-10-15 PT PT08838625T patent/PT2212323E/pt unknown
- 2008-10-15 CA CA2703037A patent/CA2703037A1/en not_active Abandoned
- 2008-10-15 AU AU2008313773A patent/AU2008313773B2/en not_active Ceased
- 2008-10-16 TW TW097139735A patent/TW200922570A/zh unknown
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2010
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- 2010-04-16 TN TN2010000167A patent/TN2010000167A1/fr unknown
- 2010-05-11 CO CO10056124A patent/CO6270321A2/es not_active Application Discontinuation
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| US8367662B2 (en) | 2013-02-05 |
| BRPI0817434A2 (pt) | 2015-06-16 |
| AR068877A1 (es) | 2009-12-09 |
| TN2010000167A1 (en) | 2011-11-11 |
| JP2011500623A (ja) | 2011-01-06 |
| AU2008313773A1 (en) | 2009-04-23 |
| CN101827844B (zh) | 2013-08-14 |
| CL2008003056A1 (es) | 2009-07-31 |
| CO6270321A2 (es) | 2011-04-20 |
| EP2212323A2 (en) | 2010-08-04 |
| IL204720A0 (en) | 2010-11-30 |
| PE20091383A1 (es) | 2009-10-17 |
| AU2008313773A8 (en) | 2010-04-29 |
| KR20100076022A (ko) | 2010-07-05 |
| TW200922570A (en) | 2009-06-01 |
| AU2008313773B2 (en) | 2012-04-12 |
| PL2212323T3 (pl) | 2013-01-31 |
| WO2009050183A2 (en) | 2009-04-23 |
| EP2212323B1 (en) | 2012-08-15 |
| ZA201002334B (en) | 2011-03-30 |
| MX2010004244A (es) | 2010-04-30 |
| JP5456681B2 (ja) | 2014-04-02 |
| ES2393430T3 (es) | 2012-12-21 |
| EA201000615A1 (ru) | 2010-12-30 |
| PT2212323E (pt) | 2012-11-27 |
| WO2009050183A3 (en) | 2009-07-16 |
| US20100210641A1 (en) | 2010-08-19 |
| MA31766B1 (fr) | 2010-10-01 |
| CN101827844A (zh) | 2010-09-08 |
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