ES2551744T3 - Nuevos compuestos de tiofeno para uso en terapia - Google Patents
Nuevos compuestos de tiofeno para uso en terapia Download PDFInfo
- Publication number
- ES2551744T3 ES2551744T3 ES09820849.9T ES09820849T ES2551744T3 ES 2551744 T3 ES2551744 T3 ES 2551744T3 ES 09820849 T ES09820849 T ES 09820849T ES 2551744 T3 ES2551744 T3 ES 2551744T3
- Authority
- ES
- Spain
- Prior art keywords
- compounds
- mice
- day
- ftaa
- compound
- 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.)
- Active
Links
- 238000002560 therapeutic procedure Methods 0.000 title 1
- 150000003577 thiophenes Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract description 66
- 150000003839 salts Chemical class 0.000 abstract description 8
- -1 carboxy, carboxy Chemical group 0.000 abstract description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000004103 aminoalkyl group Chemical group 0.000 abstract 1
- 241000699670 Mus sp. Species 0.000 description 22
- 108010064539 amyloid beta-protein (1-42) Proteins 0.000 description 19
- 210000004556 brain Anatomy 0.000 description 19
- 201000010099 disease Diseases 0.000 description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 15
- 241001465754 Metazoa Species 0.000 description 13
- 206010002022 amyloidosis Diseases 0.000 description 12
- 210000004027 cell Anatomy 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- 239000002953 phosphate buffered saline Substances 0.000 description 12
- 108091000054 Prion Proteins 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000007912 intraperitoneal administration Methods 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 206010061592 cardiac fibrillation Diseases 0.000 description 9
- 230000002600 fibrillogenic effect Effects 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 238000001727 in vivo Methods 0.000 description 8
- 102000004169 proteins and genes Human genes 0.000 description 8
- 108090000623 proteins and genes Proteins 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 102000029797 Prion Human genes 0.000 description 7
- 239000003814 drug Substances 0.000 description 7
- 239000000523 sample Substances 0.000 description 7
- 230000001225 therapeutic effect Effects 0.000 description 7
- 238000011830 transgenic mouse model Methods 0.000 description 7
- 241000699660 Mus musculus Species 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000002776 aggregation Effects 0.000 description 6
- 238000004220 aggregation Methods 0.000 description 6
- 238000004113 cell culture Methods 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 238000011534 incubation Methods 0.000 description 6
- 210000003734 kidney Anatomy 0.000 description 6
- 210000004185 liver Anatomy 0.000 description 6
- 210000002569 neuron Anatomy 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 231100000419 toxicity Toxicity 0.000 description 6
- 230000001988 toxicity Effects 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 208000024777 Prion disease Diseases 0.000 description 5
- 208000015181 infectious disease Diseases 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 102000004196 processed proteins & peptides Human genes 0.000 description 5
- 108090000765 processed proteins & peptides Proteins 0.000 description 5
- 241000894007 species Species 0.000 description 5
- 102100034452 Alternative prion protein Human genes 0.000 description 4
- 208000020406 Creutzfeldt Jacob disease Diseases 0.000 description 4
- 208000003407 Creutzfeldt-Jakob Syndrome Diseases 0.000 description 4
- 208000010859 Creutzfeldt-Jakob disease Diseases 0.000 description 4
- 241000282414 Homo sapiens Species 0.000 description 4
- 208000018756 Variant Creutzfeldt-Jakob disease Diseases 0.000 description 4
- 238000003556 assay Methods 0.000 description 4
- 230000002950 deficient Effects 0.000 description 4
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000013074 reference sample Substances 0.000 description 4
- 238000005070 sampling Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 239000011550 stock solution Substances 0.000 description 4
- 208000023769 AA amyloidosis Diseases 0.000 description 3
- 208000024827 Alzheimer disease Diseases 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000287828 Gallus gallus Species 0.000 description 3
- 241000282412 Homo Species 0.000 description 3
- 238000000134 MTT assay Methods 0.000 description 3
- 231100000002 MTT assay Toxicity 0.000 description 3
- 241001529936 Murinae Species 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- 108010071690 Prealbumin Proteins 0.000 description 3
- 238000006069 Suzuki reaction reaction Methods 0.000 description 3
- 101150052863 THY1 gene Proteins 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 102000009190 Transthyretin Human genes 0.000 description 3
- 230000008499 blood brain barrier function Effects 0.000 description 3
- 210000001218 blood-brain barrier Anatomy 0.000 description 3
- 208000005881 bovine spongiform encephalopathy Diseases 0.000 description 3
- 230000003833 cell viability Effects 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 3
- 210000002257 embryonic structure Anatomy 0.000 description 3
- 238000003818 flash chromatography Methods 0.000 description 3
- 230000002068 genetic effect Effects 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 230000007774 longterm Effects 0.000 description 3
- 230000035772 mutation Effects 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 230000004083 survival effect Effects 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 230000009885 systemic effect Effects 0.000 description 3
- 230000009261 transgenic effect Effects 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- 208000023761 AL amyloidosis Diseases 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 108010090849 Amyloid beta-Peptides Proteins 0.000 description 2
- 102000013455 Amyloid beta-Peptides Human genes 0.000 description 2
- 108010048112 Amyloidogenic Proteins Proteins 0.000 description 2
- 102000009091 Amyloidogenic Proteins Human genes 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- 206010016202 Familial Amyloidosis Diseases 0.000 description 2
- 102000008946 Fibrinogen Human genes 0.000 description 2
- 108010049003 Fibrinogen Proteins 0.000 description 2
- 102000004878 Gelsolin Human genes 0.000 description 2
- 108090001064 Gelsolin Proteins 0.000 description 2
- 208000005531 Immunoglobulin Light-chain Amyloidosis Diseases 0.000 description 2
- 102000004877 Insulin Human genes 0.000 description 2
- 108090001061 Insulin Proteins 0.000 description 2
- 102000036770 Islet Amyloid Polypeptide Human genes 0.000 description 2
- 108010041872 Islet Amyloid Polypeptide Proteins 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 102000016943 Muramidase Human genes 0.000 description 2
- 108010014251 Muramidase Proteins 0.000 description 2
- 108010062010 N-Acetylmuramoyl-L-alanine Amidase Proteins 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 238000006619 Stille reaction Methods 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 108010064397 amyloid beta-protein (1-40) Proteins 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 230000027455 binding Effects 0.000 description 2
- 238000009395 breeding Methods 0.000 description 2
- 230000001488 breeding effect Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000034994 death Effects 0.000 description 2
- 231100000517 death Toxicity 0.000 description 2
- 235000013601 eggs Nutrition 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229940012952 fibrinogen Drugs 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 230000002440 hepatic effect Effects 0.000 description 2
- 238000011577 humanized mouse model Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 229940125396 insulin Drugs 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 230000003902 lesion Effects 0.000 description 2
- 239000004325 lysozyme Substances 0.000 description 2
- 229960000274 lysozyme Drugs 0.000 description 2
- 235000010335 lysozyme Nutrition 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 238000010172 mouse model Methods 0.000 description 2
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 2
- 210000003061 neural cell Anatomy 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 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 2
- 238000001542 size-exclusion chromatography Methods 0.000 description 2
- 210000001587 telencephalon Anatomy 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 239000013638 trimer Substances 0.000 description 2
- 230000035899 viability Effects 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- YMMGRPLNZPTZBS-UHFFFAOYSA-N 2,3-dihydrothieno[2,3-b][1,4]dioxine Chemical compound O1CCOC2=C1C=CS2 YMMGRPLNZPTZBS-UHFFFAOYSA-N 0.000 description 1
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
- 238000011818 5xFAD mouse Methods 0.000 description 1
- 208000036850 AGel amyloidosis Diseases 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 102000011767 Acute-Phase Proteins Human genes 0.000 description 1
- 108010062271 Acute-Phase Proteins Proteins 0.000 description 1
- 201000004384 Alopecia Diseases 0.000 description 1
- 108010094108 Amyloid Proteins 0.000 description 1
- 102000001049 Amyloid Human genes 0.000 description 1
- 208000037259 Amyloid Plaque Diseases 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 108010085443 Anserine Proteins 0.000 description 1
- 241000615866 Antho Species 0.000 description 1
- 101710095342 Apolipoprotein B Proteins 0.000 description 1
- 102100040202 Apolipoprotein B-100 Human genes 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 102000055006 Calcitonin Human genes 0.000 description 1
- 108060001064 Calcitonin Proteins 0.000 description 1
- 206010007509 Cardiac amyloidosis Diseases 0.000 description 1
- 206010007559 Cardiac failure congestive Diseases 0.000 description 1
- 208000005145 Cerebral amyloid angiopathy Diseases 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 108020005199 Dehydrogenases Proteins 0.000 description 1
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 201000007888 Finnish type amyloidosis Diseases 0.000 description 1
- CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical compound O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 0.000 description 1
- 229930182566 Gentamicin Natural products 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 229910004373 HOAc Inorganic materials 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 208000023105 Huntington disease Diseases 0.000 description 1
- 102000013463 Immunoglobulin Light Chains Human genes 0.000 description 1
- 108010065825 Immunoglobulin Light Chains Proteins 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- PIWKPBJCKXDKJR-UHFFFAOYSA-N Isoflurane Chemical compound FC(F)OC(Cl)C(F)(F)F PIWKPBJCKXDKJR-UHFFFAOYSA-N 0.000 description 1
- SLRNWACWRVGMKD-UHFFFAOYSA-N L-anserine Natural products CN1C=NC(CC(NC(=O)CCN)C(O)=O)=C1 SLRNWACWRVGMKD-UHFFFAOYSA-N 0.000 description 1
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
- 229930182816 L-glutamine Natural products 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 208000034578 Multiple myelomas Diseases 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- 206010035226 Plasma cell myeloma Diseases 0.000 description 1
- 241000221945 Podospora Species 0.000 description 1
- 101100070542 Podospora anserina het-s gene Proteins 0.000 description 1
- 241000210053 Potentilla elegans Species 0.000 description 1
- 108010007288 PrPSc Proteins Proteins 0.000 description 1
- 206010036673 Primary amyloidosis Diseases 0.000 description 1
- 102000001708 Protein Isoforms Human genes 0.000 description 1
- 108010029485 Protein Isoforms Proteins 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 206010039811 Secondary amyloidosis Diseases 0.000 description 1
- 102000054727 Serum Amyloid A Human genes 0.000 description 1
- 108700028909 Serum Amyloid A Proteins 0.000 description 1
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 1
- 229920001872 Spider silk Polymers 0.000 description 1
- 102000019259 Succinate Dehydrogenase Human genes 0.000 description 1
- 108010012901 Succinate Dehydrogenase Proteins 0.000 description 1
- 102000003978 Tissue Plasminogen Activator Human genes 0.000 description 1
- 108090000373 Tissue Plasminogen Activator Proteins 0.000 description 1
- COQLPRJCUIATTQ-UHFFFAOYSA-N Uranyl acetate Chemical compound O.O.O=[U]=O.CC(O)=O.CC(O)=O COQLPRJCUIATTQ-UHFFFAOYSA-N 0.000 description 1
- 101150099178 abo gene Proteins 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008043 acidic salts Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 102000003802 alpha-Synuclein Human genes 0.000 description 1
- 108090000185 alpha-Synuclein Proteins 0.000 description 1
- 230000007792 alzheimer disease pathology Effects 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- PLOPBXQQPZYQFA-AXPWDRQUSA-N amlintide Chemical compound C([C@@H](C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H]1NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](NC(=O)[C@@H](N)CCCCN)CSSC1)[C@@H](C)O)C(C)C)C1=CC=CC=C1 PLOPBXQQPZYQFA-AXPWDRQUSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000003941 amyloidogenesis Effects 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- MYYIAHXIVFADCU-QMMMGPOBSA-N anserine Chemical compound CN1C=NC=C1C[C@H](NC(=O)CC[NH3+])C([O-])=O MYYIAHXIVFADCU-QMMMGPOBSA-N 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 150000001543 aryl boronic acids Chemical group 0.000 description 1
- 150000001502 aryl halides Chemical class 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- 238000004638 bioanalytical method Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 1
- BBBFJLBPOGFECG-VJVYQDLKSA-N calcitonin Chemical compound N([C@H](C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(N)=O)C(C)C)C(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1 BBBFJLBPOGFECG-VJVYQDLKSA-N 0.000 description 1
- 229960004015 calcitonin Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001735 carboxylic acids Chemical group 0.000 description 1
- 239000006143 cell culture medium Substances 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 230000036755 cellular response Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 210000001638 cerebellum Anatomy 0.000 description 1
- 210000001175 cerebrospinal fluid Anatomy 0.000 description 1
- 210000004720 cerebrum Anatomy 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 208000037976 chronic inflammation Diseases 0.000 description 1
- 230000006020 chronic inflammation Effects 0.000 description 1
- 230000007370 cognitive improvement Effects 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 229940125890 compound Ia Drugs 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000007821 culture assay Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- YFXCNIVBAVFOBX-UHFFFAOYSA-N ethenylboronic acid Chemical compound OB(O)C=C YFXCNIVBAVFOBX-UHFFFAOYSA-N 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000007701 flash-distillation Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 238000001502 gel electrophoresis Methods 0.000 description 1
- 229960002518 gentamicin Drugs 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 159000000011 group IA salts Chemical class 0.000 description 1
- 230000003676 hair loss Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000000004 hemodynamic effect Effects 0.000 description 1
- 208000017105 hereditary amyloidosis Diseases 0.000 description 1
- 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 1
- 238000009396 hybridization Methods 0.000 description 1
- 230000000642 iatrogenic effect Effects 0.000 description 1
- 239000003547 immunosorbent Substances 0.000 description 1
- 201000008319 inclusion body myositis Diseases 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 206010022437 insomnia Diseases 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 229960002725 isoflurane Drugs 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 206010023497 kuru Diseases 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 210000002780 melanosome Anatomy 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 238000005649 metathesis reaction Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000002438 mitochondrial effect Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- JHNLMNSDAFLKIB-RUDMXATFSA-N n,n-dimethyl-n'-(6-methyl-5-nitro-4-oxo-1h-pyrimidin-2-yl)methanimidamide Chemical compound CN(C)\C=N\C1=NC(C)=C([N+]([O-])=O)C(=O)N1 JHNLMNSDAFLKIB-RUDMXATFSA-N 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 125000002577 pseudohalo group Chemical group 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 208000008864 scrapie Diseases 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 210000000225 synapse Anatomy 0.000 description 1
- 230000007354 synaptic deterioration Effects 0.000 description 1
- 210000001103 thalamus Anatomy 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- ARYHTUPFQTUBBG-UHFFFAOYSA-N thiophen-2-ylboronic acid Chemical compound OB(O)C1=CC=CS1 ARYHTUPFQTUBBG-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 150000008648 triflates Chemical class 0.000 description 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 230000036325 urinary excretion Effects 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 238000001262 western blot Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/28—Halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D333/40—Thiophene-2-carboxylic acid
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Diabetes (AREA)
- Psychology (AREA)
- Epidemiology (AREA)
- Hospice & Palliative Care (AREA)
- Obesity (AREA)
- Endocrinology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Hematology (AREA)
- Psychiatry (AREA)
- Emergency Medicine (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0850043 | 2008-10-17 | ||
| SE0850043 | 2008-10-17 | ||
| SE0850050 | 2008-10-23 | ||
| SE0850050 | 2008-10-23 | ||
| PCT/SE2009/051187 WO2010044743A1 (en) | 2008-10-17 | 2009-10-19 | Novel thiophene compounds for use in theraphy |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2551744T3 true ES2551744T3 (es) | 2015-11-23 |
Family
ID=42106726
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES09820849.9T Active ES2551744T3 (es) | 2008-10-17 | 2009-10-19 | Nuevos compuestos de tiofeno para uso en terapia |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8710246B2 (OSRAM) |
| EP (1) | EP2350042B1 (OSRAM) |
| JP (1) | JP5646495B2 (OSRAM) |
| KR (1) | KR101743049B1 (OSRAM) |
| CN (1) | CN102256959B (OSRAM) |
| BR (1) | BRPI0920850A2 (OSRAM) |
| CA (1) | CA2740969C (OSRAM) |
| ES (1) | ES2551744T3 (OSRAM) |
| WO (2) | WO2010044744A1 (OSRAM) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012009484A2 (en) | 2010-07-13 | 2012-01-19 | Stc.Unm | Structure, synthesis, and applications for poly (phenylene) ethynylenes (ppes) |
| US9125415B2 (en) | 2011-07-08 | 2015-09-08 | Stc, Unm | Thiophene based oligomers as light activated biocides |
| EP2817304A4 (en) * | 2011-07-14 | 2015-01-21 | Biochromix Newco Ab | Novel compounds and their use in therapy |
| WO2013020096A2 (en) | 2011-08-03 | 2013-02-07 | Stc.Unm | Antimicrobial materials and methods |
| WO2013036196A1 (en) * | 2011-09-07 | 2013-03-14 | Biochromix Ab | Novel thiophene compounds and method for in vivo imaging |
| SE536793C2 (sv) | 2012-07-02 | 2014-08-19 | Richter Life Science Dev Ab | Detektion av kolhydrater |
| US9968698B2 (en) | 2013-11-08 | 2018-05-15 | Stc. Unm | Charged singlet-oxygen sensitizers and oppositely-charged surfactants |
| WO2015138965A1 (en) | 2014-03-14 | 2015-09-17 | Whitten David G | P-phenylene ethynylene compounds as bioactive and detection agents |
| KR101913057B1 (ko) | 2015-01-14 | 2018-10-29 | 유니버시티 오브 플로리다 리서치 파운데이션, 인크. | 공액 고분자 전해질 및 이의 사용 방법 |
| WO2017058085A1 (en) | 2015-10-01 | 2017-04-06 | Richter Life Science Development Ab | Detection of microbial peptides |
| US10772851B2 (en) | 2017-02-03 | 2020-09-15 | Aaron Kurt Neumann | Treatment and prevention of fungal infections |
| US20200261605A1 (en) * | 2019-01-24 | 2020-08-20 | Alzeca Biosciences, LLC | Functionalized liposomes for imaging misfolded proteins |
| CN119264384A (zh) * | 2023-07-04 | 2025-01-07 | 宁德时代未来能源(上海)研究院有限公司 | 化合物、钙钛矿太阳能电池和用电装置 |
| CN118724890A (zh) * | 2024-06-05 | 2024-10-01 | 佛山大学 | 一种抗细菌生物膜剂的荧光示踪成像探针分子及其制备方法和应用 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63158557A (ja) * | 1986-12-23 | 1988-07-01 | Fuji Electric Co Ltd | 電子写真用感光体 |
| US4861692A (en) * | 1986-12-22 | 1989-08-29 | Fuji Electric Company, Ltd. | Electrophotographic photosensitive material containing thiophene compound |
| US5747525A (en) * | 1992-02-19 | 1998-05-05 | Industrial Technology Research Institute | Medicinal thiophene compounds |
| JP3885244B2 (ja) | 1994-12-05 | 2007-02-21 | 松下電器産業株式会社 | オリゴチオフェン重合体、及びオリゴチオフェン化合物の製造方法 |
| CA2272275A1 (en) * | 1996-11-26 | 1998-06-04 | Purdue Research Foundation | Polythiophene anti-tumor agents |
| US6730929B2 (en) | 1999-12-24 | 2004-05-04 | Matsushita Electric Industrial Co., Ltd. | Organic electroluminescent device |
| TW200413009A (en) * | 2002-10-04 | 2004-08-01 | Univ Pennsylvania | Biphenyls and fluorenes as imaging agents in alzheimer's disease |
| WO2005002288A1 (ja) * | 2003-03-14 | 2005-01-06 | Semiconductor Energy Laboratory Co., Ltd. | 共役分子及びそれを用いた電界発光素子、並びに電界発光素子を用いた電子機器 |
| SE0401219D0 (sv) * | 2004-05-10 | 2004-05-10 | Biochromix Ab | Metoder för detektera konformationsförändringar eller aggregering hos proteiner med hjälp av konjugerade polyelektrolyter |
| JP4392499B2 (ja) * | 2004-12-07 | 2010-01-06 | 国立大学法人 筑波大学 | キラルポリマーの製造方法及びキラルポリマー並びにキラルポリマーの動的な電気化学的方法による光学活性制御 |
| JPWO2007063950A1 (ja) * | 2005-12-01 | 2009-05-07 | 国立大学法人東北大学 | コンフォーメーション病診断および治療用の長波長蛍光物質およびその使用 |
| EP1996951A1 (en) * | 2006-02-09 | 2008-12-03 | BioChromix AB | Methods for detection of pathogenic prion proteins associated with prion diseases, using conjugated polyelectrolytes |
| WO2007109545A2 (en) * | 2006-03-16 | 2007-09-27 | The Regents Of The University Of California | Copolymers of alkoxythiophene |
| BRPI0806621A2 (pt) * | 2007-01-22 | 2011-09-13 | Astrazeneca Ab | composto, uso de um composto, composição farmacêutica, e, método in vivo para medir depósitos amilóides em um indivìduo |
| EP2236142A1 (en) | 2007-04-18 | 2010-10-06 | Biochromix Pharma AB | Medical use of conjugated polyelectrolytes |
-
2009
- 2009-10-19 US US13/124,621 patent/US8710246B2/en not_active Expired - Fee Related
- 2009-10-19 BR BRPI0920850A patent/BRPI0920850A2/pt not_active IP Right Cessation
- 2009-10-19 ES ES09820849.9T patent/ES2551744T3/es active Active
- 2009-10-19 EP EP09820849.9A patent/EP2350042B1/en not_active Not-in-force
- 2009-10-19 JP JP2011532044A patent/JP5646495B2/ja not_active Expired - Fee Related
- 2009-10-19 WO PCT/SE2009/051188 patent/WO2010044744A1/en not_active Ceased
- 2009-10-19 WO PCT/SE2009/051187 patent/WO2010044743A1/en not_active Ceased
- 2009-10-19 CN CN200980151290.7A patent/CN102256959B/zh not_active Expired - Fee Related
- 2009-10-19 KR KR1020117011029A patent/KR101743049B1/ko not_active Expired - Fee Related
- 2009-10-19 CA CA2740969A patent/CA2740969C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2740969A1 (en) | 2010-04-22 |
| EP2350042A1 (en) | 2011-08-03 |
| BRPI0920850A2 (pt) | 2016-09-13 |
| CA2740969C (en) | 2017-01-17 |
| US20120157516A1 (en) | 2012-06-21 |
| EP2350042B1 (en) | 2015-07-29 |
| JP5646495B2 (ja) | 2014-12-24 |
| CN102256959A (zh) | 2011-11-23 |
| JP2012505879A (ja) | 2012-03-08 |
| KR101743049B1 (ko) | 2017-06-02 |
| EP2350042A4 (en) | 2013-07-31 |
| KR20110099089A (ko) | 2011-09-06 |
| WO2010044744A1 (en) | 2010-04-22 |
| CN102256959B (zh) | 2014-01-08 |
| WO2010044743A1 (en) | 2010-04-22 |
| US8710246B2 (en) | 2014-04-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES2551744T3 (es) | Nuevos compuestos de tiofeno para uso en terapia | |
| US12398092B2 (en) | Method for inhibiting or disrupting biofilm formation, or reducing biofilm | |
| TW201823266A (zh) | 含二硫化物細胞穿透肽及其製造與使用方法 | |
| JP2016074679A (ja) | 化合物 | |
| KR20150132325A (ko) | 아민 작용성 폴리아미드 | |
| CN103467417A (zh) | 牛蒡子苷元碳酰胺衍生物及其制备方法、包含该衍生物的组合物、及其用途 | |
| KR20240008882A (ko) | 약학적 활성 화합물로서 레조르시놀 유도체 및 이의 제조방법 | |
| US9334251B2 (en) | Compounds for the treatment of neurodegenerative diseases | |
| CN102186464B (zh) | 用于预防淀粉状蛋白沉积物和治疗涉及淀粉状蛋白生成的疾病的萘醌衍生物 | |
| JP6159388B2 (ja) | タンパク質凝集の阻害剤としてのフェニル−尿素及びフェニル−カルバメート誘導体 | |
| US20090074833A1 (en) | Bridged polycyclic compound based compositions for controlling bone resorption | |
| KR20160005356A (ko) | 방사선완화 약제학적 제형 | |
| Biswas et al. | Synthesis of ibuprofen conjugated molecular transporter capable of enhanced brain penetration | |
| WO2015175704A1 (en) | Inhibitors of bacterial dna gyrase with efficacy against gram-negative bacteria | |
| JP7371838B2 (ja) | 環縮合チアゾリノ２－ピリドン、それらの調製方法、ならびにグラム陽性菌が関与する疾患の治療および／または予防におけるそれらの使用 | |
| MX2011003809A (es) | Composiciones y metodos para tratar o prevenir heridas hipoxica o isquemica. | |
| US20240374573A1 (en) | Imidazole containing compounds, derivatives therefore, and uses thereof | |
| AU2015287661B2 (en) | Main chain polyamines | |
| WO2020182144A1 (zh) | 用于治疗神经退行性疾病的化合物 | |
| BR112021011860A2 (pt) | Conjugados | |
| CN110117302B (zh) | 神经退行性疾病的治疗药物及其应用 | |
| CN110612305B (zh) | 硫酸乙酰肝素糖模拟化合物及其医药与化妆品用途 | |
| PT796841E (pt) | Esteres bis alcanoilo de carnitina com actividade bactericida fungicida e anriprotozoaria | |
| ES2948122A1 (es) | Compuestos para el tratamiento y/o prevención de una infección o enfermedad causada por Helicobacter o Campylobacter |