HRP20140628T1 - Metoda za dobivanje novih derivata naftalena za dijagnosticiranje alzheimerove bolesti in vivo - Google Patents
Metoda za dobivanje novih derivata naftalena za dijagnosticiranje alzheimerove bolesti in vivo Download PDFInfo
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- HRP20140628T1 HRP20140628T1 HRP20140628AT HRP20140628T HRP20140628T1 HR P20140628 T1 HRP20140628 T1 HR P20140628T1 HR P20140628A T HRP20140628A T HR P20140628AT HR P20140628 T HRP20140628 T HR P20140628T HR P20140628 T1 HRP20140628 T1 HR P20140628T1
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- Prior art keywords
- alkyl
- naphthalene derivatives
- solvent
- alkylenyl
- dmf
- Prior art date
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- 238000000034 method Methods 0.000 title claims 7
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical class C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 title claims 3
- 208000024827 Alzheimer disease Diseases 0.000 title 1
- 238000003745 diagnosis Methods 0.000 title 1
- 238000001727 in vivo Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 6
- 150000002790 naphthalenes Chemical class 0.000 claims 6
- 239000002904 solvent Substances 0.000 claims 5
- 238000006243 chemical reaction Methods 0.000 claims 4
- 150000004985 diamines Chemical class 0.000 claims 4
- -1 succinimidyl group Chemical group 0.000 claims 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- FXJMMPAVUBUMAD-UHFFFAOYSA-N 4-(naphthalen-1-ylamino)-4-oxobutanoic acid Chemical compound C1=CC=C2C(NC(=O)CCC(=O)O)=CC=CC2=C1 FXJMMPAVUBUMAD-UHFFFAOYSA-N 0.000 claims 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 150000003512 tertiary amines Chemical class 0.000 claims 2
- NIJWNEHRVSLYJB-UHFFFAOYSA-N 1-naphthalen-1-ylpyrrolidine-2,5-dione Chemical compound O=C1CCC(=O)N1C1=CC=CC2=CC=CC=C12 NIJWNEHRVSLYJB-UHFFFAOYSA-N 0.000 claims 1
- HCXJFMDOHDNDCC-UHFFFAOYSA-N 5-$l^{1}-oxidanyl-3,4-dihydropyrrol-2-one Chemical group O=C1CCC(=O)[N]1 HCXJFMDOHDNDCC-UHFFFAOYSA-N 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- 208000037259 Amyloid Plaque Diseases 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 238000005481 NMR spectroscopy Methods 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- 125000005466 alkylenyl group Chemical group 0.000 claims 1
- 150000001371 alpha-amino acids Chemical class 0.000 claims 1
- 235000008206 alpha-amino acids Nutrition 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 150000001414 amino alcohols Chemical class 0.000 claims 1
- 210000004556 brain Anatomy 0.000 claims 1
- 125000005467 butylenyl group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 238000002405 diagnostic procedure Methods 0.000 claims 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 230000014509 gene expression Effects 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 238000011065 in-situ storage Methods 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 238000009206 nuclear medicine Methods 0.000 claims 1
- 238000005580 one pot reaction Methods 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 claims 1
- 238000002600 positron emission tomography Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 238000002603 single-photon emission computed tomography Methods 0.000 claims 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims 1
- 230000001052 transient effect Effects 0.000 claims 1
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/041—Heterocyclic compounds
- A61K51/044—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins
- A61K51/0446—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/0402—Organic compounds carboxylic acid carriers, fatty acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/0474—Organic compounds complexes or complex-forming compounds, i.e. wherein a radioactive metal (e.g. 111In3+) is complexed or chelated by, e.g. a N2S2, N3S, NS3, N4 chelating group
- A61K51/0482—Organic compounds complexes or complex-forming compounds, i.e. wherein a radioactive metal (e.g. 111In3+) is complexed or chelated by, e.g. a N2S2, N3S, NS3, N4 chelating group chelates from cyclic ligands, e.g. DOTA
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/04—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C233/07—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/35—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/36—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/47—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/24—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/25—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/06—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with radicals, containing only hydrogen and carbon atoms, attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
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- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
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- Veterinary Medicine (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Claims (12)
1. Spojevi derivirani iz naftalena, naznačeni strukturom I,
[image]
U strukturi I, izrazi označeni kao R su:
R1: -alkilenil-C(O)NH-alkilenil-R3, -alkilenil-C(O)O-R4;
R3: -COOH, -OH, -SH, -NH2, -NH-alkil, -N-alkil –ditiokarbamat soli zemnoalkalnih metala;
R4: sukcinimidil skupina;
R2: -H, -alkil, gdje je izraz "alkil" naznačen linearnim ili razgranatim alifatskim lancem, atomima vodika i zasićenog ugljika, koji uključuje neku metil, etil, n-propil, izo-propil,n-butil, izo-butil grupu; izraz "alkilenil" odnosi se na dvovalentni analogni spoj linearne ili razgranate alkilne skupine, po mogućnosti etilenil, CH2CH2, ili butilenil, CH2CH2CH2CH2, radikale.
2. Derivati naftalena prema zahtjevu 1, naznačeni time da je: R1 je - (CH2)nCONH(CH2)m-R3 (n =2, 3 ili 4 a m = 2, 3, 4, 5 ili 6), R3 je -COO, -OH, -SH, -NH2, -NHCH3 ili -NHC2H5, a R2 je -H, -alkil; i kombinacije koje iz njih proizlaze.
3. Derivati naftalena prema zahtjevu 1, naznačeni time da je: R1 is - (CH2)nCONH(CH2)m-R3 (n = 2, 3 ili 4 a m = 2, 3, 4, 5 ili 6), R3je OH, SH, ili -NR4R5, R4 is -H, -CH3 ili -C2H5, R5 is C(S)SW, W je Na+, K+ ili Cs+ a R2 je -H, - alkil; alkil; i kombinacije koje iz njih proizlaze
4. Derivati naftalena prema zahtjevu 1, naznačeni time da je: R1 je - (CH2)nC(O)O-R4 (n= 2, 3 ili 4), R4 je sukcinimidil radikal, a R2 je -H, -alkil; i kombinacije koje iz njih proizlaze.
5. Postupak za pripremu derivata naftalena strukture I, prema zahtjevima 1 i 2, koji u R1 nose neku kiselinsku ili amino terminalnu skupinu, naznačen reakcijom acilacijskog sredstva, N-hidroksisukcinamid estera 4-(1-naftalimino)-4-oksobutanoične kiseline prema zahtjevu 4, pri čemu spojevi imaju primarne amino skupine kao što su alifatski diamini, linearni ili razgranati, i polifunkcionalne amine kao što su α-amino kiseline, tioamini, aminoalkoholi i aminokarboksilne kiseline, u prisutnosti neke organske baze ili bez nje, u DMF-u ili 1,4-dioksanu kao otapalu.
6. Postupak prema zahtjevu 5 gdje se derivati naftalena dobiju pomoću neke tehnike „u jednom loncu“, naznačen reakcijom 4-(1-naftilamino)- 4- oksobutanoične kiseline s NHS u prisutnosti DCC, da bi se in situ dobio prijelazni N-hidroksisukdinimid ester 4-(1-naftilamino)-4-oksobutanoične kiseline prema zahtjevu 4, i njegovom neposrednom reakcijom s viškom diamina ili aminokarboksilne kiseline na sobnoj temperaturi te s DMF-om ili 1, 4–dioksanom kao otapalom.
7. Postupak prema zahtjevu 5, naznačen time da se derivati naftalena dobiju reakcijom 1-(1-naftil)-2,5-pirolidinediona, s viškom diamina, na sobnoj temperaturi i s 1,4-dioksanom kao otapalom ili s viškom diamina, u prisutnosti nekog tercijarnog amina, po mogućnosti trieltilamina pri temperaturi refluksa i s DMF-om kao otapalom.
8. Postupak prema zahtjevu 7, naznačen time da se koristi neki diamin, u prisutnosti jednog tercijarnog amina, po mogućnosti trietilamina, na sobnoj temperaturi i DMF kao otapalo.
9. Spojevi prema zahtjevu 1, naznačeni time da su povezani s jednim jodnim radioizotopom koji emitira gama zrake, koji se uobičajeno koristi u nuklearnoj medicini (123I ili 131I).
10. Spojevi prema zahtjevu 1, naznačeni time da s 99mTc tvore stabilne komplekse.
11. Spojevi prema zahtjevu 1, naznačeni time da u svojoj strukturi imaju jedan izotop koji emitira pozitrone, kao što je 11C, 15O ili 18F.
12. Spoj definiran u zahtjevima 9, 10 i 11 za primjenu u dijagnostičkoj metodi za prikazivanje gustoće amiloidnih plakova u mozgu sisavaca korištenjem tehnike kompjuterizirane tomografije emisijom jednog fotona (SPECT), pozitronske emisione tomografije (PET) ili nuklearne magnetske rezonancije (MRI).
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CU2009000057A CU23844B1 (es) | 2009-04-17 | 2009-04-17 | Procedimiento de obtención de nuevos derivados de naftaleno para el diagnóstico in vivo de la enfermedad de alzheimer |
| PCT/CU2010/000001 WO2010118706A2 (es) | 2009-04-17 | 2010-04-17 | Procedimiento de obtención de nuevos derivados de naftaleno para el diagnóstico in vivo de la enfermedad de alzheimer |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20140628T1 true HRP20140628T1 (hr) | 2014-11-21 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20140628AT HRP20140628T1 (hr) | 2009-04-17 | 2014-07-01 | Metoda za dobivanje novih derivata naftalena za dijagnosticiranje alzheimerove bolesti in vivo |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US9764047B2 (hr) |
| EP (2) | EP2436666B1 (hr) |
| BR (2) | BR122020016643B8 (hr) |
| CA (1) | CA2789869C (hr) |
| CU (1) | CU23844B1 (hr) |
| DK (1) | DK2436666T3 (hr) |
| ES (2) | ES2692072T3 (hr) |
| HR (1) | HRP20140628T1 (hr) |
| HU (1) | HUE042030T2 (hr) |
| MX (2) | MX2011013405A (hr) |
| MY (1) | MY162719A (hr) |
| PL (1) | PL2436666T3 (hr) |
| PT (1) | PT2436666E (hr) |
| SI (1) | SI2436666T1 (hr) |
| SM (1) | SMT201400118B (hr) |
| WO (1) | WO2010118706A2 (hr) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CU20130027A7 (es) * | 2013-02-28 | 2014-10-30 | Ct De Neurociencias De Cuba | Chaperoninas químicas como nuevos moduladores moleculares de la beta agregación proteica presente en las enfermedades conformacionales |
| WO2015200187A1 (en) | 2014-06-27 | 2015-12-30 | Reiley Pharmaceuticals, Inc. | Conjugates derived from non-steroidal anti-inflammatory drugs and methods of use thereof in imaging |
| US10053478B2 (en) | 2015-01-09 | 2018-08-21 | Reiley Pharmaceuticals, Inc. | COX-2-targeting, platinum-containing conjugates and their use in the treatment of tumors and cancers |
| CU24583B1 (es) * | 2018-11-06 | 2022-02-04 | Centro De Neurociencias De Cuba | Nanopartículas de óxido metálicos conjugados con derivados de naftaleno como agentes de contrastes para la detección de placas amiloides por resonancia magnética (mri) |
| US11828210B2 (en) | 2020-08-20 | 2023-11-28 | Denso International America, Inc. | Diagnostic systems and methods of vehicles using olfaction |
| US11636870B2 (en) | 2020-08-20 | 2023-04-25 | Denso International America, Inc. | Smoking cessation systems and methods |
| US11760169B2 (en) | 2020-08-20 | 2023-09-19 | Denso International America, Inc. | Particulate control systems and methods for olfaction sensors |
| US11881093B2 (en) | 2020-08-20 | 2024-01-23 | Denso International America, Inc. | Systems and methods for identifying smoking in vehicles |
| US11932080B2 (en) | 2020-08-20 | 2024-03-19 | Denso International America, Inc. | Diagnostic and recirculation control systems and methods |
| US11760170B2 (en) | 2020-08-20 | 2023-09-19 | Denso International America, Inc. | Olfaction sensor preservation systems and methods |
| US11813926B2 (en) | 2020-08-20 | 2023-11-14 | Denso International America, Inc. | Binding agent and olfaction sensor |
| CU20200087A7 (es) | 2020-11-24 | 2022-07-08 | Centro De Neurociencias De Cuba | Composición farmacéutica de derivados de naftaleno como agentes terapéuticos multiblancos para el tratamiento de la enfermedad de alzheimer |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| DK2436666T3 (da) | 2014-07-14 |
| EP2436666A4 (en) | 2013-02-13 |
| US10155053B2 (en) | 2018-12-18 |
| MX338943B (es) | 2016-05-06 |
| BR122020016643B1 (pt) | 2021-03-30 |
| US20120321560A1 (en) | 2012-12-20 |
| HUE042030T2 (hu) | 2019-06-28 |
| MY162719A (en) | 2017-07-14 |
| WO2010118706A2 (es) | 2010-10-21 |
| CA2789869A1 (en) | 2010-10-21 |
| EP2860169A3 (en) | 2015-10-21 |
| CU20090057A6 (es) | 2011-10-14 |
| PT2436666E (pt) | 2014-07-18 |
| BRPI1014595A2 (pt) | 2016-04-05 |
| PL2436666T3 (pl) | 2014-09-30 |
| ES2692072T3 (es) | 2018-11-30 |
| BR122020016643B8 (pt) | 2021-07-27 |
| EP2436666B1 (en) | 2014-04-09 |
| SMT201400118B (it) | 2014-11-10 |
| SI2436666T1 (sl) | 2014-09-30 |
| BRPI1014595B1 (pt) | 2021-07-06 |
| EP2436666A2 (en) | 2012-04-04 |
| WO2010118706A3 (es) | 2010-12-02 |
| ES2478442T3 (es) | 2014-07-22 |
| WO2010118706A4 (es) | 2011-01-20 |
| US9764047B2 (en) | 2017-09-19 |
| CA2789869C (en) | 2016-06-21 |
| US20150217005A1 (en) | 2015-08-06 |
| CU23844B1 (es) | 2012-10-15 |
| EP2860169B1 (en) | 2018-08-29 |
| EP2860169A2 (en) | 2015-04-15 |
| MX2011013405A (es) | 2012-10-23 |
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