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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- 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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- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
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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)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
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- Ophthalmology & Optometry (AREA)
- Otolaryngology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (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 |
|---|---|---|---|
| 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 |
|---|---|
| CA2724842A1 true CA2724842A1 (en) | 2009-11-26 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| CA2724842A Abandoned CA2724842A1 (en) | 2008-05-19 | 2009-05-19 | Imidazo[1,2-a]pyridine compounds |
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| Country | Link |
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| US (2) | US8497278B2 (enExample) |
| EP (1) | EP2300470A2 (enExample) |
| JP (2) | JP5774982B2 (enExample) |
| AU (1) | AU2009249186B2 (enExample) |
| CA (1) | CA2724842A1 (enExample) |
| WO (1) | WO2009143156A2 (enExample) |
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| EP2213672A4 (en) * | 2007-10-24 | 2012-05-02 | Nihon Mediphysics Co Ltd | NEW CONNECTION WITH AFFINITY TO AMYLOID |
| EP2493889B1 (en) | 2009-10-30 | 2017-09-06 | Janssen Pharmaceutica, N.V. | IMIDAZO[1,2-b]PYRIDAZINE DERIVATIVES AND THEIR USE AS PDE10 INHIBITORS |
| EP2496578A4 (en) | 2009-11-05 | 2013-08-21 | Univ Notre Dame Du Lac | IMIDAZO [1,2-A] PYRIDINE COMPOUNDS, THEIR SYNTHESIS AND METHODS OF USE THEREOF |
| 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 |
| WO2011150156A2 (en) | 2010-05-26 | 2011-12-01 | Sunovion Pharmaceuticals Inc. | Heteroaryl compounds and methods of use thereof |
| US20140221354A1 (en) * | 2011-03-31 | 2014-08-07 | Emblem Technology Transfer Gmbh | IMIDAZO [1,2-a]PYRIDINE COMPOUNDS FOR USE IN THERAPY |
| MX344600B (es) | 2011-06-27 | 2016-12-20 | Janssen Pharmaceutica Nv | Derivados de 1-aril-4-metil-[1,2,4]triazolo[4,3-a]quinoxalina. |
| EP2854804B1 (en) * | 2012-05-30 | 2019-11-20 | F.Hoffmann-La Roche Ag | Pyrrolidino heterocycles |
| HK1206250A1 (en) | 2012-06-26 | 2016-01-08 | Janssen Pharmaceutica Nv | Combinations comprising pde 2 inhibitors such as 1-aryl-4-methyl-[1,2,4] triazolo [4,3-a] quinoxaline compounds and ped 10 inhibitors for use in the treatment of neurological or metabolic disorders |
| CN104411314B (zh) | 2012-07-09 | 2017-10-20 | 詹森药业有限公司 | 磷酸二酯酶10的抑制剂 |
| 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 |
| AU2016324598A1 (en) | 2015-09-17 | 2018-03-15 | Marvin J. Miller | Benzyl amine-containing heterocyclic compounds and compositions useful against mycobacterial infection |
| NO3153506T3 (enExample) * | 2015-10-07 | 2018-05-12 | ||
| EP3365340B1 (en) | 2015-10-19 | 2022-08-10 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| HUE060680T2 (hu) | 2015-11-19 | 2023-04-28 | Incyte Corp | Heterociklusos vegyületek mint immunmodulátorok |
| 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 |
| EA201891374A1 (ru) | 2015-12-10 | 2018-11-30 | Байер Фарма Акциенгезельшафт | Замещенные 2-фенил-3-(пиперазинметил)имидазопиридины и их применение |
| EP3394033B1 (en) | 2015-12-22 | 2020-11-25 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| WO2017192961A1 (en) | 2016-05-06 | 2017-11-09 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| TW201808902A (zh) | 2016-05-26 | 2018-03-16 | 美商英塞特公司 | 作為免疫調節劑之雜環化合物 |
| MD3472167T2 (ro) | 2016-06-20 | 2023-02-28 | Incyte Corp | Compuși heterociclici ca 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 |
| US20180057486A1 (en) | 2016-08-29 | 2018-03-01 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| EA202192558A1 (ru) * | 2016-12-14 | 2021-12-07 | Байер Акциенгезельшафт | Замещенные диазагетеробициклические соединения и их применение |
| PE20200005A1 (es) | 2016-12-22 | 2020-01-06 | Incyte Corp | Derivados de tetrahidro imidazo[4,5-c]piridina como inductores de internalizacion pd-l1 |
| EP3558989B1 (en) | 2016-12-22 | 2021-04-14 | Incyte Corporation | Triazolo[1,5-a]pyridine derivatives as immunomodulators |
| EP3558973B1 (en) | 2016-12-22 | 2021-09-15 | Incyte Corporation | Pyridine derivatives as immunomodulators |
| EP3558963B1 (en) | 2016-12-22 | 2022-03-23 | Incyte Corporation | Bicyclic heteroaromatic compounds as immunomodulators |
| MA47123A (fr) | 2016-12-22 | 2021-03-17 | Incyte Corp | Dérivés de benzooxazole en tant qu'mmunomodulateurs |
| 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 |
| PL4212529T3 (pl) | 2018-03-30 | 2025-07-07 | Incyte Corporation | Związki heterocykliczne jako immunomodulatory |
| HRP20230306T1 (hr) | 2018-05-11 | 2023-05-12 | Incyte Corporation | Derivati tetrahidro-imidazo[4,5-c]piridina kao pd-l1 imunomodulatori |
| EP3807269A1 (en) * | 2018-06-13 | 2021-04-21 | F. Hoffmann-La Roche AG | New isoxazolyl ether derivatives as gaba a alpha5 pam |
| 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 |
| WO2021030162A1 (en) | 2019-08-09 | 2021-02-18 | Incyte Corporation | Salts of a pd-1/pd-l1 inhibitor |
| IL291471B2 (en) | 2019-09-30 | 2025-04-01 | Incyte Corp | Pyrimido[3,2–D]pyrimidine compounds as immunomodulators |
| CR20220237A (es) | 2019-11-11 | 2022-08-05 | Incyte Corp | Sales y formas cristalinas de un inhibidor 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 |
| AR124001A1 (es) | 2020-11-06 | 2023-02-01 | Incyte Corp | Proceso para fabricar un inhibidor pd-1 / pd-l1 y sales y formas cristalinas del mismo |
| US11780836B2 (en) | 2020-11-06 | 2023-10-10 | Incyte Corporation | Process of preparing a PD-1/PD-L1 inhibitor |
| WO2022099075A1 (en) | 2020-11-06 | 2022-05-12 | Incyte Corporation | Crystalline form of a pd-1/pd-l1 inhibitor |
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| CN101218238B (zh) * | 2005-03-21 | 2011-10-26 | S*Bio私人有限公司 | 咪唑并[1,2-a]吡啶衍生物：制备及药学应用 |
| EP1912966A2 (en) * | 2005-06-01 | 2008-04-23 | Ucb, S.A. | 2-oxo-1-pyrrolidine derivatives and their therapeutic use on the central nervous system |
| AU2006278504B2 (en) * | 2005-08-04 | 2013-01-17 | Sirtris Pharmaceuticals, Inc. | Imidazopyridine derivatives as sirtuin modulating agents |
| JP2009518409A (ja) * | 2005-12-06 | 2009-05-07 | メルク エンド カムパニー インコーポレーテッド | モルホリンカルボキサミドプロキネチシン受容体アンタゴニスト |
| 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 |
| CA2667487C (en) * | 2006-11-06 | 2017-04-04 | Supergen, Inc. | Imidazo[1,2-b]pyridazine and pyrazolo[1,5-a]pyrimidine derivatives and their use as protein kinase inhibitors |
| 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 WO PCT/US2009/044525 patent/WO2009143156A2/en not_active Ceased
- 2009-05-19 JP JP2011510650A patent/JP5774982B2/ja active Active
- 2009-05-19 CA CA2724842A patent/CA2724842A1/en not_active Abandoned
- 2009-05-19 AU AU2009249186A patent/AU2009249186B2/en not_active Ceased
- 2009-05-19 EP EP09751384A patent/EP2300470A2/en not_active Ceased
- 2009-05-19 US US12/993,679 patent/US8497278B2/en not_active Expired - Fee Related
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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
Also Published As
| Publication number | Publication date |
|---|---|
| WO2009143156A3 (en) | 2010-01-14 |
| WO2009143156A2 (en) | 2009-11-26 |
| JP6211556B2 (ja) | 2017-10-11 |
| US20110166146A1 (en) | 2011-07-07 |
| AU2009249186B2 (en) | 2014-05-22 |
| US20130289013A1 (en) | 2013-10-31 |
| AU2009249186A1 (en) | 2009-11-26 |
| JP5774982B2 (ja) | 2015-09-09 |
| EP2300470A2 (en) | 2011-03-30 |
| JP2011523945A (ja) | 2011-08-25 |
| JP2015180633A (ja) | 2015-10-15 |
| US8497278B2 (en) | 2013-07-30 |
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