TWI357412B - Imidazo [1,2-a] pyridine compounds, compositions, - Google Patents
Imidazo [1,2-a] pyridine compounds, compositions, Download PDFInfo
- Publication number
- TWI357412B TWI357412B TW094139042A TW94139042A TWI357412B TW I357412 B TWI357412 B TW I357412B TW 094139042 A TW094139042 A TW 094139042A TW 94139042 A TW94139042 A TW 94139042A TW I357412 B TWI357412 B TW I357412B
- Authority
- TW
- Taiwan
- Prior art keywords
- methyl
- imidazo
- pyridin
- ylmethyl
- acid
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims description 17
- 150000005234 imidazo[1,2-a]pyridines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 61
- -1 oxygen-1, 4, 5, 6-tetrahydro-indole-3-carboxylic acid Chemical compound 0.000 claims description 34
- 238000011282 treatment Methods 0.000 claims description 15
- 206010022437 insomnia Diseases 0.000 claims description 14
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 9
- 230000006698 induction Effects 0.000 claims description 9
- 208000019901 Anxiety disease Diseases 0.000 claims description 8
- 230000036506 anxiety Effects 0.000 claims description 8
- 229940079593 drug Drugs 0.000 claims description 8
- 206010039897 Sedation Diseases 0.000 claims description 7
- 206010021118 Hypotonia Diseases 0.000 claims description 6
- 230000036640 muscle relaxation Effects 0.000 claims description 6
- 206010002091 Anaesthesia Diseases 0.000 claims description 5
- 230000037005 anaesthesia Effects 0.000 claims description 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 206010015037 epilepsy Diseases 0.000 claims description 4
- 208000019116 sleep disease Diseases 0.000 claims description 3
- QHNDFWPCDITBSG-UHFFFAOYSA-N 2-(4-methylphenyl)-1h-imidazole Chemical compound C1=CC(C)=CC=C1C1=NC=CN1 QHNDFWPCDITBSG-UHFFFAOYSA-N 0.000 claims description 2
- HJZYBDPHAHGHAZ-UHFFFAOYSA-N thiadiazole-4-carboxylic acid Chemical compound OC(=O)C1=CSN=N1 HJZYBDPHAHGHAZ-UHFFFAOYSA-N 0.000 claims description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- WLDPWZQYAVZTTP-UHFFFAOYSA-N 1-methyl-imidazole-2-carboxylic acid Chemical compound CN1C=CN=C1C(O)=O WLDPWZQYAVZTTP-UHFFFAOYSA-N 0.000 claims 1
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- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 claims 1
- 210000003296 saliva Anatomy 0.000 claims 1
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- 229930192474 thiophene Natural products 0.000 claims 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 100
- 238000004128 high performance liquid chromatography Methods 0.000 description 84
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 45
- 125000000217 alkyl group Chemical group 0.000 description 27
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- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 13
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- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 9
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- 229960005181 morphine Drugs 0.000 description 1
- 229940035363 muscle relaxants Drugs 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 1
- AQBMQGDKWIPBRF-UHFFFAOYSA-N n'-hydroxypyridine-3-carboximidamide Chemical compound ON=C(N)C1=CC=CN=C1 AQBMQGDKWIPBRF-UHFFFAOYSA-N 0.000 description 1
- YWWNNLPSZSEZNZ-UHFFFAOYSA-N n,n-dimethyldecan-1-amine Chemical compound CCCCCCCCCCN(C)C YWWNNLPSZSEZNZ-UHFFFAOYSA-N 0.000 description 1
- 125000001326 naphthylalkyl group Chemical group 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 229960003966 nicotinamide Drugs 0.000 description 1
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- 229940098462 oral drops Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000036407 pain Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- FLKPEMZONWLCSK-UHFFFAOYSA-N phthalic acid di-n-ethyl ester Natural products CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229940057838 polyethylene glycol 4000 Drugs 0.000 description 1
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- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229940068968 polysorbate 80 Drugs 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
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- 235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 230000004799 sedative–hypnotic effect Effects 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 208000024794 sputum Diseases 0.000 description 1
- 210000003802 sputum Anatomy 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical class 0.000 description 1
- YNVOMSDITJMNET-UHFFFAOYSA-N thiophene-3-carboxylic acid Chemical compound OC(=O)C=1C=CSC=1 YNVOMSDITJMNET-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000002618 waking effect Effects 0.000 description 1
- 229960001475 zolpidem Drugs 0.000 description 1
- ZAFYATHCZYHLPB-UHFFFAOYSA-N zolpidem Chemical compound N1=C2C=CC(C)=CN2C(CC(=O)N(C)C)=C1C1=CC=C(C)C=C1 ZAFYATHCZYHLPB-UHFFFAOYSA-N 0.000 description 1
- 229960000820 zopiclone Drugs 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4188—1,3-Diazoles condensed with other heterocyclic ring systems, e.g. biotin, sorbinil
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P23/00—Anaesthetics
-
- 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
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- A61P25/22—Anxiolytics
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Epidemiology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP04105698 | 2004-11-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200624432A TW200624432A (en) | 2006-07-16 |
| TWI357412B true TWI357412B (en) | 2012-02-01 |
Family
ID=34929843
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW094139042A TWI357412B (en) | 2004-11-11 | 2005-11-08 | Imidazo [1,2-a] pyridine compounds, compositions, |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US20080200473A1 (https=) |
| EP (1) | EP1814880B1 (https=) |
| JP (1) | JP2008519805A (https=) |
| KR (1) | KR20070084026A (https=) |
| CN (1) | CN101065377B (https=) |
| AR (1) | AR051626A1 (https=) |
| AT (1) | ATE421962T1 (https=) |
| AU (1) | AU2005303811A1 (https=) |
| BR (1) | BRPI0517796A (https=) |
| CA (1) | CA2585315A1 (https=) |
| DE (1) | DE602005012598D1 (https=) |
| DK (1) | DK1814880T3 (https=) |
| ES (1) | ES2321858T3 (https=) |
| IL (1) | IL182963A0 (https=) |
| MX (1) | MX2007005611A (https=) |
| NO (1) | NO20072831L (https=) |
| PA (1) | PA8652101A1 (https=) |
| PE (1) | PE20060967A1 (https=) |
| PL (1) | PL1814880T3 (https=) |
| PT (1) | PT1814880E (https=) |
| RU (1) | RU2007121864A (https=) |
| TW (1) | TWI357412B (https=) |
| UY (1) | UY29204A1 (https=) |
| WO (1) | WO2006051063A1 (https=) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1483283A4 (en) | 2002-03-13 | 2007-04-11 | Signum Biosciences Inc | MODULATION OF PROTEIN METHYLATION AND PHOSPHOPROTEIN PHOSPHATE |
| CA2601777A1 (en) | 2005-02-03 | 2006-08-10 | Signum Biosciences, Inc. | Compositions and methods for enhancing cognitive function |
| US7923041B2 (en) | 2005-02-03 | 2011-04-12 | Signum Biosciences, Inc. | Compositions and methods for enhancing cognitive function |
| 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 |
| MX2008014796A (es) * | 2006-05-31 | 2008-12-02 | Hoffmann La Roche | Derivados de aril-4-etinil-isoxazol. |
| AU2007288124B2 (en) * | 2006-08-24 | 2013-04-04 | Australian Nuclear Science & Technology Organisation | Fluorinated ligands for targeting peripheral benzodiazepine receptors |
| AU2009239430B2 (en) | 2008-04-21 | 2015-01-22 | Signum Biosciences, Inc. | Compounds, compositions and methods for making the same |
| CA2724842A1 (en) | 2008-05-19 | 2009-11-26 | Sunovion Pharmaceuticals Inc. | Imidazo[1,2-a]pyridine compounds |
| WO2010045615A2 (en) | 2008-10-16 | 2010-04-22 | Cenomed Biosciences, Llc | Treatment of organophosphate exposure with ocinaplon |
| EP2376490B1 (en) * | 2008-12-04 | 2013-01-23 | Proximagen Limited | Imidazopyridine compounds |
| 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 |
| WO2012036278A1 (ja) * | 2010-09-17 | 2012-03-22 | 大正製薬株式会社 | グリシントランスポーター阻害物質 |
| CN108348510B (zh) | 2015-09-17 | 2022-01-04 | 圣母大学 | 针对分枝杆菌感染有用的含有苄胺的杂环化合物以及组合物 |
| WO2017087885A1 (en) | 2015-11-19 | 2017-05-26 | Dana-Farber Cancer Institute, Inc. | Methods of identifying compounds that interfere with erg-driven misguidance of baf complexes in tmprss2-erg driven prostate cancers |
| CN106906486B (zh) * | 2017-02-22 | 2018-12-11 | 华南理工大学 | 3-溴-2-苯基-咪唑并[1,2-α]吡啶类衍生物的电化学合成方法 |
| US11497752B2 (en) | 2018-01-30 | 2022-11-15 | Foghorn Therapeutics Inc. | Compounds and uses thereof |
| WO2020081588A1 (en) | 2018-10-17 | 2020-04-23 | Dana-Farber Cancer Institute, Inc. | Swi/snf family chromatin remodeling complexes and uses thereof |
| US12509453B2 (en) | 2019-01-29 | 2025-12-30 | Foghorn Therapeutics Inc. | BRM/BRG1 inhibitors and uses thereof |
| US12384776B2 (en) | 2019-01-29 | 2025-08-12 | Foghorn Therapeutics Inc. | Compounds and uses thereof |
| AU2021213811A1 (en) | 2020-01-29 | 2022-07-28 | Foghorn Therapeutics Inc. | Compounds and uses thereof |
| WO2021155264A1 (en) * | 2020-01-29 | 2021-08-05 | Foghorn Therapeutics Inc. | Compounds and uses thereof |
| US12383555B2 (en) | 2020-05-20 | 2025-08-12 | Foghorn Therapeutics Inc. | Methods of treating cancers |
| US12606553B2 (en) | 2021-03-09 | 2026-04-21 | Foghorn Therapeutics Inc. | Crystalline forms, compositions containing same, and methods of their use |
| KR20260004434A (ko) * | 2023-04-24 | 2026-01-08 | 상하이 에스아이엠알 바이오테크놀로지 컴퍼니 리미티드 | 이미다조피리딘 또는 이미다조피라진 화합물, 이의 제조 방법, 약학 조성물 및 용도 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| FR2593818B1 (fr) * | 1986-02-05 | 1988-04-29 | Synthelabo | Derives d'acylaminomethyl-3 imidazo(1,2-a)pyridine, leur preparation et leur application en therapeutique |
| ES2032455T3 (es) * | 1986-01-22 | 1993-02-16 | Synthelabo | Procedimiento para preparar derivados de 3-acilaminometil-imidazo (-1,2-a)piridinas. |
| FR2593181B1 (fr) * | 1986-01-22 | 1988-04-01 | Synthelabo | Derives d'acylaminomethyl-3 imidazo(1,2-a)pyridines, leur preparation et leur application en therapeutique |
| US20040204443A1 (en) * | 2003-01-27 | 2004-10-14 | Arthur Zaks | Method for inducing pain relief using imidazo[1,2-a]pyridine derivatives |
-
2005
- 2005-11-04 RU RU2007121864/04A patent/RU2007121864A/ru not_active Application Discontinuation
- 2005-11-04 AU AU2005303811A patent/AU2005303811A1/en not_active Abandoned
- 2005-11-04 DK DK05808135T patent/DK1814880T3/da active
- 2005-11-04 AT AT05808135T patent/ATE421962T1/de active
- 2005-11-04 ES ES05808135T patent/ES2321858T3/es not_active Expired - Lifetime
- 2005-11-04 KR KR1020077010318A patent/KR20070084026A/ko not_active Ceased
- 2005-11-04 PT PT05808135T patent/PT1814880E/pt unknown
- 2005-11-04 EP EP05808135A patent/EP1814880B1/en not_active Expired - Lifetime
- 2005-11-04 PL PL05808135T patent/PL1814880T3/pl unknown
- 2005-11-04 DE DE602005012598T patent/DE602005012598D1/de not_active Expired - Lifetime
- 2005-11-04 JP JP2007540634A patent/JP2008519805A/ja active Pending
- 2005-11-04 MX MX2007005611A patent/MX2007005611A/es active IP Right Grant
- 2005-11-04 US US11/667,494 patent/US20080200473A1/en not_active Abandoned
- 2005-11-04 WO PCT/EP2005/055753 patent/WO2006051063A1/en not_active Ceased
- 2005-11-04 BR BRPI0517796-0A patent/BRPI0517796A/pt not_active IP Right Cessation
- 2005-11-04 CN CN2005800386913A patent/CN101065377B/zh not_active Expired - Fee Related
- 2005-11-04 CA CA002585315A patent/CA2585315A1/en not_active Abandoned
- 2005-11-07 PE PE2005001302A patent/PE20060967A1/es not_active Application Discontinuation
- 2005-11-08 PA PA20058652101A patent/PA8652101A1/es unknown
- 2005-11-08 TW TW094139042A patent/TWI357412B/zh not_active IP Right Cessation
- 2005-11-09 AR ARP050104693A patent/AR051626A1/es not_active Application Discontinuation
- 2005-11-10 UY UY29204A patent/UY29204A1/es not_active Application Discontinuation
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2007
- 2007-05-03 IL IL182963A patent/IL182963A0/en unknown
- 2007-06-04 NO NO20072831A patent/NO20072831L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| UY29204A1 (es) | 2006-01-31 |
| PA8652101A1 (es) | 2006-10-13 |
| NO20072831L (no) | 2007-08-01 |
| CN101065377B (zh) | 2011-07-27 |
| US20080200473A1 (en) | 2008-08-21 |
| TW200624432A (en) | 2006-07-16 |
| RU2007121864A (ru) | 2008-12-20 |
| ATE421962T1 (de) | 2009-02-15 |
| JP2008519805A (ja) | 2008-06-12 |
| EP1814880A1 (en) | 2007-08-08 |
| CA2585315A1 (en) | 2006-05-18 |
| DK1814880T3 (da) | 2009-05-18 |
| PL1814880T3 (pl) | 2009-07-31 |
| CN101065377A (zh) | 2007-10-31 |
| AU2005303811A1 (en) | 2006-05-18 |
| EP1814880B1 (en) | 2009-01-28 |
| AR051626A1 (es) | 2007-01-24 |
| ES2321858T3 (es) | 2009-06-12 |
| IL182963A0 (en) | 2007-08-19 |
| WO2006051063A1 (en) | 2006-05-18 |
| PT1814880E (pt) | 2009-04-23 |
| PE20060967A1 (es) | 2006-09-20 |
| DE602005012598D1 (de) | 2009-03-19 |
| KR20070084026A (ko) | 2007-08-24 |
| BRPI0517796A (pt) | 2008-10-28 |
| MX2007005611A (es) | 2007-07-11 |
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