CA2724842A1 - Imidazo[1,2-a]pyridine compounds - Google Patents
Imidazo[1,2-a]pyridine compounds Download PDFInfo
- Publication number
- CA2724842A1 CA2724842A1 CA2724842A CA2724842A CA2724842A1 CA 2724842 A1 CA2724842 A1 CA 2724842A1 CA 2724842 A CA2724842 A CA 2724842A CA 2724842 A CA2724842 A CA 2724842A CA 2724842 A1 CA2724842 A1 CA 2724842A1
- Authority
- CA
- Canada
- Prior art keywords
- substituted
- unsubstituted
- methyl
- compound
- imidazo
- 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
- 150000005234 imidazo[1,2-a]pyridines Chemical class 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 540
- 238000000034 method Methods 0.000 claims abstract description 242
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 229
- -1 benzoimidazolyl Chemical group 0.000 claims description 204
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 157
- 229910052739 hydrogen Inorganic materials 0.000 claims description 118
- 229910052805 deuterium Inorganic materials 0.000 claims description 108
- 125000000217 alkyl group Chemical group 0.000 claims description 104
- 239000000203 mixture Substances 0.000 claims description 82
- 208000002193 Pain Diseases 0.000 claims description 69
- 125000003118 aryl group Chemical group 0.000 claims description 63
- 125000001072 heteroaryl group Chemical group 0.000 claims description 57
- 230000036407 pain Effects 0.000 claims description 57
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 50
- 150000003839 salts Chemical class 0.000 claims description 45
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 40
- 125000001424 substituent group Chemical group 0.000 claims description 36
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 35
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 35
- 229910052736 halogen Inorganic materials 0.000 claims description 35
- 150000002367 halogens Chemical class 0.000 claims description 33
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 30
- 229910052799 carbon Inorganic materials 0.000 claims description 27
- 206010010904 Convulsion Diseases 0.000 claims description 25
- 125000004429 atom Chemical group 0.000 claims description 24
- 208000019901 Anxiety disease Diseases 0.000 claims description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- 229910052717 sulfur Inorganic materials 0.000 claims description 22
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical group C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims description 20
- 125000005842 heteroatom Chemical group 0.000 claims description 18
- 125000004122 cyclic group Chemical group 0.000 claims description 17
- 201000010099 disease Diseases 0.000 claims description 17
- 208000035475 disorder Diseases 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 16
- 102000004300 GABA-A Receptors Human genes 0.000 claims description 15
- 108090000839 GABA-A Receptors Proteins 0.000 claims description 15
- 239000000460 chlorine Substances 0.000 claims description 14
- 125000002252 acyl group Chemical group 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 208000010877 cognitive disease Diseases 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 206010047700 Vomiting Diseases 0.000 claims description 9
- 208000020925 Bipolar disease Diseases 0.000 claims description 8
- 208000007101 Muscle Cramp Diseases 0.000 claims description 8
- 208000005392 Spasm Diseases 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 208000020401 Depressive disease Diseases 0.000 claims description 7
- 208000030814 Eating disease Diseases 0.000 claims description 7
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 235000014632 disordered eating Nutrition 0.000 claims description 7
- 208000030533 eye disease Diseases 0.000 claims description 7
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 7
- 230000004770 neurodegeneration Effects 0.000 claims description 7
- 230000000626 neurodegenerative effect Effects 0.000 claims description 7
- 206010001488 Aggression Diseases 0.000 claims description 6
- 230000016571 aggressive behavior Effects 0.000 claims description 6
- 208000012761 aggressive behavior Diseases 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 230000003001 depressive effect Effects 0.000 claims description 6
- 208000020016 psychiatric disease Diseases 0.000 claims description 6
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 5
- 125000002950 monocyclic group Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 201000000980 schizophrenia Diseases 0.000 claims description 5
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 4
- 206010049816 Muscle tightness Diseases 0.000 claims description 4
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000002619 bicyclic group Chemical group 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 125000002720 diazolyl group Chemical group 0.000 claims description 4
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 4
- AQIAIZBHFAKICS-UHFFFAOYSA-N methylaminomethyl Chemical compound [CH2]NC AQIAIZBHFAKICS-UHFFFAOYSA-N 0.000 claims description 4
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
- 125000001425 triazolyl group Chemical group 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 125000002393 azetidinyl group Chemical group 0.000 claims description 3
- 125000005872 benzooxazolyl group Chemical group 0.000 claims description 3
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 125000002632 imidazolidinyl group Chemical group 0.000 claims description 3
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 claims description 3
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 3
- 125000000160 oxazolidinyl group Chemical group 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- 125000004306 triazinyl group Chemical group 0.000 claims description 3
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 2
- 101100478297 Arabidopsis thaliana SR45 gene Proteins 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 150000001539 azetidines Chemical class 0.000 claims description 2
- 150000002461 imidazolidines Chemical class 0.000 claims description 2
- XYMVZPOXZCDCNP-UHFFFAOYSA-N sulfamoyl cyanide Chemical compound NS(=O)(=O)C#N XYMVZPOXZCDCNP-UHFFFAOYSA-N 0.000 claims 2
- 239000003814 drug Substances 0.000 abstract description 84
- 229940124597 therapeutic agent Drugs 0.000 abstract description 70
- 238000011282 treatment Methods 0.000 abstract description 23
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 233
- 101150041968 CDC13 gene Proteins 0.000 description 231
- 238000005160 1H NMR spectroscopy Methods 0.000 description 209
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 86
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 70
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 69
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
- NPPMHVCZUGFSLQ-UHFFFAOYSA-N 3-(chloromethyl)-6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridine;hydrochloride Chemical compound Cl.C1=CC(C)=CC=C1C1=C(CCl)N2C=C(C)C=CC2=N1 NPPMHVCZUGFSLQ-UHFFFAOYSA-N 0.000 description 59
- 229910052740 iodine Inorganic materials 0.000 description 58
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 56
- 229940125904 compound 1 Drugs 0.000 description 50
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- OIIOPWHTJZYKIL-PMACEKPBSA-N (5S)-5-[[[5-[2-chloro-3-[2-chloro-3-[6-methoxy-5-[[[(2S)-5-oxopyrrolidin-2-yl]methylamino]methyl]pyrazin-2-yl]phenyl]phenyl]-3-methoxypyrazin-2-yl]methylamino]methyl]pyrrolidin-2-one Chemical compound C1(=C(N=C(C2=C(C(C3=CC=CC(=C3Cl)C3=NC(OC)=C(N=C3)CNC[C@H]3NC(=O)CC3)=CC=C2)Cl)C=N1)OC)CNC[C@H]1NC(=O)CC1 OIIOPWHTJZYKIL-PMACEKPBSA-N 0.000 description 43
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 42
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 40
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- 239000000243 solution Substances 0.000 description 37
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- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 32
- 230000001225 therapeutic effect Effects 0.000 description 31
- JQWJOSZRYINDTA-UHFFFAOYSA-N 3-(chloromethyl)-2-(4-chlorophenyl)imidazo[1,2-a]pyridine;hydrochloride Chemical compound Cl.N1=C2C=CC=CN2C(CCl)=C1C1=CC=C(Cl)C=C1 JQWJOSZRYINDTA-UHFFFAOYSA-N 0.000 description 29
- 238000006243 chemical reaction Methods 0.000 description 29
- 238000010898 silica gel chromatography Methods 0.000 description 27
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 26
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- OKKJLVBELUTLKV-MZCSYVLQSA-N CD3OD Substances [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 23
- DQAZPZIYEOGZAF-UHFFFAOYSA-N 4-ethyl-n-[4-(3-ethynylanilino)-7-methoxyquinazolin-6-yl]piperazine-1-carboxamide Chemical compound C1CN(CC)CCN1C(=O)NC(C(=CC1=NC=N2)OC)=CC1=C2NC1=CC=CC(C#C)=C1 DQAZPZIYEOGZAF-UHFFFAOYSA-N 0.000 description 22
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Classifications
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- 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
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- A61P25/00—Drugs for disorders of the nervous system
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- 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
- C07D487/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
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- Chemical & Material Sciences (AREA)
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- Anesthesiology (AREA)
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- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
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| US5443208P | 2008-05-19 | 2008-05-19 | |
| US5443708P | 2008-05-19 | 2008-05-19 | |
| US61/054,432 | 2008-05-19 | ||
| US61/054,437 | 2008-05-19 | ||
| PCT/US2009/044525 WO2009143156A2 (en) | 2008-05-19 | 2009-05-19 | IMIDAZO[1,2-a]PYRIDINE COMPOUNDS |
Publications (1)
| Publication Number | Publication Date |
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| CA2724842A1 true CA2724842A1 (en) | 2009-11-26 |
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| CA2724842A Abandoned CA2724842A1 (en) | 2008-05-19 | 2009-05-19 | Imidazo[1,2-a]pyridine compounds |
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| AU (1) | AU2009249186B2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2724842A1 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2009143156A2 (cg-RX-API-DMAC7.html) |
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| TW200918102A (en) * | 2007-10-24 | 2009-05-01 | Nihon Mediphysics Co Ltd | Novel compound having affinity for amyloid |
| KR101774035B1 (ko) | 2009-10-30 | 2017-09-01 | 얀센 파마슈티카 엔.브이. | 이미다조［１，２―ｂ］피리다진 유도체 및 ＰＤＥ１０ 저해제로서의 그의 용도 |
| EP3257854A1 (en) * | 2009-11-05 | 2017-12-20 | University of Notre Dame du Lac | Imidazo[1,2-a]pyridine compounds, synthesis thereof, and methods of using same |
| AR080754A1 (es) | 2010-03-09 | 2012-05-09 | Janssen Pharmaceutica Nv | Derivados de imidazo (1,2-a) pirazina y su uso como inhibidores de pde10 |
| CA2800618C (en) | 2010-05-26 | 2018-08-28 | Sunovion Pharmaceuticals Inc. | Heteroaryl compounds and methods of use thereof |
| WO2012130322A1 (en) * | 2011-03-31 | 2012-10-04 | Elara Pharmaceuticals Gmbh | Imidazo [1,2-a]pyridine compounds for use in therapy |
| EA027418B1 (ru) | 2011-06-27 | 2017-07-31 | Янссен Фармацевтика Нв | ПРОИЗВОДНЫЕ 1-АРИЛ-4-МЕТИЛ[1,2,4]ТРИАЗОЛО[4,3-a]ХИНОКСАЛИНА, ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ НА ИХ ОСНОВЕ, СПОСОБЫ ПОЛУЧЕНИЯ И ПРИМЕНЕНИЯ ИХ, ПРОМЕЖУТОЧНЫЕ СОЕДИНЕНИЯ |
| CA2869535A1 (en) * | 2012-05-30 | 2013-12-05 | F. Hoffmann-La Roche Ag | Pyrrolidino heterocycles |
| ES2855575T3 (es) | 2012-06-26 | 2021-09-23 | Janssen Pharmaceutica Nv | Combinaciones que comprenden compuestos de 4-metil-[1,2,4]triazolo[4,3-a]quinoxalina como inhibidores de PDE2 e inhibidores de PDE10 para su uso en el tratamiento de trastornos neurológicos o metabólicos |
| KR102171706B1 (ko) | 2012-07-09 | 2020-10-30 | 얀센 파마슈티카 엔.브이. | 포스포디에스테라아제 10 효소의 억제제 |
| JP2016527184A (ja) | 2013-05-24 | 2016-09-08 | イオメット ファーマ リミテッド | Ｓｌｃ２ａ輸送体阻害剤 |
| PE20181352A1 (es) | 2015-09-17 | 2018-08-22 | Marvin J Miller | Compuestos heterociclicos que contienen bencilamina y composiciones utiles contra infeccion por micobacterias |
| PT3153506T (pt) * | 2015-10-07 | 2018-03-22 | Sanko Tekstil Isletmeleri San Ve Tic As | Isoxazoles, um processo para a sua preparação e seus usos |
| WO2017070089A1 (en) | 2015-10-19 | 2017-04-27 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| US20170145025A1 (en) | 2015-11-19 | 2017-05-25 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| CA3007724C (en) | 2015-12-10 | 2023-10-17 | Bayer Pharma Aktiengesellschaft | 2-phenyl-3-(piperazinomethyl)imidazo[1,2-a]pyridine derivatives as blockers of task-1 and task-2 channels, for the treatment of sleep-related breathing disorders |
| JP2018538296A (ja) | 2015-12-10 | 2018-12-27 | バイエル・ファルマ・アクティエンゲゼルシャフト | 置換ペルヒドロピロロ［３，４−ｃ］ピロール誘導体およびその使用 |
| LT3394033T (lt) | 2015-12-22 | 2021-03-10 | Incyte Corporation | Heterocikliniai junginiai, kaip imunomoduliatoriai |
| US20170320875A1 (en) | 2016-05-06 | 2017-11-09 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| US20170342060A1 (en) | 2016-05-26 | 2017-11-30 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| HRP20221030T1 (hr) | 2016-06-20 | 2022-11-11 | Incyte Corporation | Heterociklički spojevi kao imunomodulatori |
| WO2018013789A1 (en) | 2016-07-14 | 2018-01-18 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| JOP20190005A1 (ar) | 2016-07-20 | 2019-01-20 | Bayer Ag | مركبات ديازاهيترو ثنائية الحلقة مستبدلة واستخداماتها |
| CN106279123B (zh) * | 2016-08-15 | 2018-09-04 | 郑州大学 | 3-(苯磺酰甲基)咪唑并杂环类化合物及其合成方法 |
| MA46045A (fr) | 2016-08-29 | 2021-04-28 | Incyte Corp | Composés hétérocycliques utilisés comme immunomodulateurs |
| EA039175B1 (ru) * | 2016-12-14 | 2021-12-14 | Байер Акциенгезельшафт | Замещенные диазагетеробициклические соединения, способ их получения и их применение |
| WO2018119221A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Pyridine derivatives as immunomodulators |
| EP3558963B1 (en) | 2016-12-22 | 2022-03-23 | Incyte Corporation | Bicyclic heteroaromatic compounds as immunomodulators |
| WO2018119236A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Triazolo[1,5-a]pyridine derivatives as immunomodulators |
| JP7149276B2 (ja) | 2016-12-22 | 2022-10-06 | インサイト・コーポレイション | Ｐｄ－ｌ１内在化誘導物質としてのテトラヒドロイミダゾ［４，５－ｃ］ピリジン誘導体 |
| BR112019012993A2 (pt) | 2016-12-22 | 2019-12-03 | Incyte Corporation | derivados de benzo-oxazol como imunomoduladores |
| CN107163039A (zh) * | 2017-05-11 | 2017-09-15 | 浙江工业大学 | 一种6‑甲基‑2‑对甲苯基咪唑并[1,2‑a]吡啶‑3‑甲醛的制备方法 |
| JOP20190284A1 (ar) | 2017-06-14 | 2019-12-11 | Bayer Pharma AG | مركبات إيميدازوبيريميدين مستبدلة بديازا ثنائي الحلقة واستخدامها للمعالجة من اضطرابات التنفس |
| WO2018227427A1 (en) | 2017-06-14 | 2018-12-20 | Bayer Aktiengesellschaft | Substituted bridged diazepane derivatives and use thereof |
| MY210070A (en) | 2018-03-30 | 2025-08-25 | Incyte Corp | Heterocyclic compounds as immunomodulators |
| PT3790877T (pt) | 2018-05-11 | 2023-05-10 | Incyte Corp | Derivados de tetrahidro-imidazo[4,5-c]piridina como imunomoduladores pd-l1 |
| PE20210555A1 (es) * | 2018-06-13 | 2021-03-17 | Hoffmann La Roche | Nuevos derivados de isoxazolil eter como pam de gaba a alfa5 |
| CN110964020B (zh) * | 2018-09-28 | 2022-06-14 | 中国科学院大连化学物理研究所 | 一种制备3’,4’-二氢螺[吲哚啉-3,2’-吡咯]化合物的方法 |
| SG11202106706TA (en) * | 2018-12-29 | 2021-07-29 | Wuhan Ll Science And Technology Development Co Ltd | Heterocyclic compound intermediate, preparation method therefor and application thereof |
| TW202115059A (zh) | 2019-08-09 | 2021-04-16 | 美商英塞特公司 | Ｐｄ—１／ｐｄ—ｌ１抑制劑之鹽 |
| BR112022005826A2 (pt) | 2019-09-30 | 2022-06-21 | Incyte Corp | Compostos de pirido[3,2-d]pirimidina como imunomoduladores |
| BR112022009031A2 (pt) | 2019-11-11 | 2022-10-11 | Incyte Corp | Sais e formas cristalinas de um inibidor de pd-1/pd-l1 |
| CN114380819B (zh) * | 2020-10-22 | 2024-08-23 | 鲁南制药集团股份有限公司 | 一种唑吡坦中间体化合物 |
| TW202233615A (zh) | 2020-11-06 | 2022-09-01 | 美商英塞特公司 | Ｐｄ—１／ｐｄ—ｌ１抑制劑之結晶形式 |
| MX2023005362A (es) | 2020-11-06 | 2023-06-22 | Incyte Corp | Proceso para hacer un inhibidor de proteina de muerte programada 1 (pd-1)/ligando de muerte programada 1 (pd-l1) y sales y formas cristalinas del mismo. |
| WO2022099018A1 (en) | 2020-11-06 | 2022-05-12 | Incyte Corporation | Process of preparing a pd-1/pd-l1 inhibitor |
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| GB991589A (en) * | 1963-04-30 | 1965-05-12 | Selvi & C Lab Bioterapico | Novel [1,2-ª‡]imidazopyridines and a process for the manufacture thereof |
| US3489755A (en) * | 1966-08-03 | 1970-01-13 | Pfizer & Co C | Imidazo (1,2-b) pyridazines |
| US4242513A (en) * | 1979-03-05 | 1980-12-30 | Appleton Papers Inc. | Lactone compounds containing a heterocyclic radical |
| GB8305245D0 (en) * | 1983-02-25 | 1983-03-30 | Fujisawa Pharmaceutical Co | Imidazo-heterocyclic compounds |
| FR2568880B1 (fr) * | 1984-08-07 | 1986-12-12 | Synthelabo | Derives d'acylaminomethyl-3 imidazo(1,2-a)pyridines, leur preparation et leur application en therapeutique |
| ATE62687T1 (de) * | 1986-01-22 | 1991-05-15 | Synthelabo | Acylaminomethylimidazo(1,2-a>pyrimidinderivate, ihre herstellung und therapeutische verwendung. |
| WO1989001333A1 (en) * | 1987-08-07 | 1989-02-23 | The Australian National University | IMIDAZO[1,2-b]PYRIDAZINES |
| IN179789B (cg-RX-API-DMAC7.html) * | 1992-02-10 | 1997-12-06 | Council Scient Ind Res | |
| FR2714907B1 (fr) * | 1994-01-07 | 1996-03-29 | Union Pharma Scient Appl | Nouveaux dérivés de l'Adénosine, leurs procédés de préparation, compositions pharmaceutiques les contenant. |
| JPH09176165A (ja) * | 1995-12-25 | 1997-07-08 | Nippon Nohyaku Co Ltd | イミダゾ［１，２−ａ］ピリジン誘導体、その製法およびその用途 |
| US6552037B2 (en) * | 2000-06-30 | 2003-04-22 | Neurogen Corporation | 2-Substituted imidazo[1,2-A]pyridine derivatives |
| US6514969B2 (en) * | 2000-08-16 | 2003-02-04 | Boehringer Ingelheim Pharma Kg | β-amyloid inhibitors, processes for preparing them, and their use in pharmaceutical compositions |
| DE10040016A1 (de) * | 2000-08-16 | 2002-02-28 | Boehringer Ingelheim Pharma | Neue beta-Amyloid Inhibitoren, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel |
| SE0100567D0 (sv) * | 2001-02-20 | 2001-02-20 | Astrazeneca Ab | Compounds |
| DE602004029272D1 (de) * | 2003-10-28 | 2010-11-04 | Sepracor Inc | Imidazoä1,2-aüpyridin-anxiolytika |
| WO2005080355A1 (en) * | 2004-02-12 | 2005-09-01 | Neurogen Corporation | Imidazo-pyridazines, triazolo-pyridazines and related benzodiazepine receptor ligands |
| RU2007121864A (ru) * | 2004-11-11 | 2008-12-20 | Феррер Интернасионал | ИМИДАЗО[1,2-a]ПИРИДИНОВЫЕ СОЕДИНЕНИЯ (ВАРИАНТЫ), СПОСОБ ИХ ПОЛУЧЕНИЯ (ВАРИАНТЫ), КОМПОЗИЦИЯ НА ИХ ОСНОВЕ, СПОСОБ ЛЕЧЕНИЯ ИЛИ ПРОФИЛАКТИКИ ЗАБОЛЕВАНИЙ, СВЯЗАННЫХ С МОДУЛЯЦИЕЙ РЕЦЕПТОРОВ GABAA, ИЛИ α1-GABAA, ИЛИ α2-GABAA (ВАРИАНТЫ) |
| AU2006225355B2 (en) * | 2005-03-21 | 2010-12-09 | Helsinn Healthcare Sa | Imidazo(1,2-a)pyridine derivatives: preparation and pharmaceutical applications |
| US7666880B2 (en) * | 2005-03-21 | 2010-02-23 | S*Bio Pte Ltd. | Imidazo[1,2-A]pyridine derivatives: preparation and pharmaceutical applications |
| AU2006254336B9 (en) | 2005-06-01 | 2013-02-28 | Ucb Pharma, S.A. | 2 -oxo-I -pyrrolidine derivatives/ processes for preparing them and their therapeutic use on the central nervous system |
| AU2006278397B2 (en) * | 2005-08-04 | 2013-01-17 | Sirtris Pharmaceuticals, Inc. | Oxazolopyridine derivatives as sirtuin modulators |
| AU2006322067A1 (en) * | 2005-12-06 | 2007-06-14 | Merck Sharp & Dohme Corp. | Morpholine carboxamide prokineticin receptor antagonists |
| EP1845098A1 (en) * | 2006-03-29 | 2007-10-17 | Ferrer Internacional, S.A. | Imidazo[1,2-b]pyridazines, their processes of preparation and their use as GABA receptor ligands |
| EP2054060B1 (en) * | 2006-08-24 | 2014-04-02 | Australian Nuclear Science & Technology Organisation | Fluorinated ligands for targeting peripheral benzodiazepine receptors |
| MX2009004700A (es) * | 2006-11-06 | 2009-05-15 | Supergen Inc | Derivados de imidazo[1,2-b]piridazin y pirazolo[1,5-a] pirimidina y su uso como inhibidores de proteina cinasa. |
| EP1974729A1 (en) * | 2007-03-28 | 2008-10-01 | Santhera Pharmaceuticals (Schweiz) AG | Substituted imidazopyridine derivates as melanocortin- 4 receptor antagonists |
| CA2709784A1 (en) * | 2007-12-21 | 2009-07-09 | University Of Rochester | Method for altering the lifespan of eukaryotic organisms |
-
2009
- 2009-05-19 AU AU2009249186A patent/AU2009249186B2/en not_active Ceased
- 2009-05-19 JP JP2011510650A patent/JP5774982B2/ja active Active
- 2009-05-19 US US12/993,679 patent/US8497278B2/en not_active Expired - Fee Related
- 2009-05-19 EP EP09751384A patent/EP2300470A2/en not_active Ceased
- 2009-05-19 WO PCT/US2009/044525 patent/WO2009143156A2/en not_active Ceased
- 2009-05-19 CA CA2724842A patent/CA2724842A1/en not_active Abandoned
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2013
- 2013-06-24 US US13/925,108 patent/US20130289013A1/en not_active Abandoned
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2015
- 2015-04-27 JP JP2015090193A patent/JP6211556B2/ja active Active
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| Publication number | Publication date |
|---|---|
| US8497278B2 (en) | 2013-07-30 |
| EP2300470A2 (en) | 2011-03-30 |
| AU2009249186A1 (en) | 2009-11-26 |
| US20110166146A1 (en) | 2011-07-07 |
| US20130289013A1 (en) | 2013-10-31 |
| JP5774982B2 (ja) | 2015-09-09 |
| WO2009143156A3 (en) | 2010-01-14 |
| JP2015180633A (ja) | 2015-10-15 |
| JP2011523945A (ja) | 2011-08-25 |
| JP6211556B2 (ja) | 2017-10-11 |
| WO2009143156A2 (en) | 2009-11-26 |
| AU2009249186B2 (en) | 2014-05-22 |
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