RU2009122198A - Производные 1,2,3-триазола в качестве ингибиторов сигма-рецепторов - Google Patents
Производные 1,2,3-триазола в качестве ингибиторов сигма-рецепторов Download PDFInfo
- Publication number
- RU2009122198A RU2009122198A RU2009122198/04A RU2009122198A RU2009122198A RU 2009122198 A RU2009122198 A RU 2009122198A RU 2009122198/04 A RU2009122198/04 A RU 2009122198/04A RU 2009122198 A RU2009122198 A RU 2009122198A RU 2009122198 A RU2009122198 A RU 2009122198A
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- Russia
- Prior art keywords
- phenyl
- triazol
- propyl
- compound
- hydrogen
- Prior art date
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- 150000000177 1,2,3-triazoles Chemical class 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 108010085082 sigma receptors Proteins 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 30
- 239000001257 hydrogen Substances 0.000 claims abstract 20
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 20
- 150000002431 hydrogen Chemical group 0.000 claims abstract 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims abstract 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract 6
- 150000003839 salts Chemical class 0.000 claims abstract 6
- 229910052736 halogen Chemical group 0.000 claims abstract 5
- 150000002367 halogens Chemical group 0.000 claims abstract 5
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 5
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract 5
- 229940002612 prodrug Drugs 0.000 claims abstract 5
- 239000000651 prodrug Substances 0.000 claims abstract 5
- 239000012453 solvate Substances 0.000 claims abstract 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims abstract 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims abstract 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract 4
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000003118 aryl group Chemical group 0.000 claims abstract 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 3
- IILGCCWJULTKPO-UHFFFAOYSA-N 1-[3-[4-(2,4-dichlorophenyl)-5-(4-methylphenyl)triazol-2-yl]propyl]piperidine Chemical compound C1=CC(C)=CC=C1C(C(=N1)C=2C(=CC(Cl)=CC=2)Cl)=NN1CCCN1CCCCC1 IILGCCWJULTKPO-UHFFFAOYSA-N 0.000 claims abstract 2
- RXLFBOFHZJXGRZ-UHFFFAOYSA-N 1-[3-[4-(4-chlorophenyl)-5-phenyltriazol-2-yl]propyl]piperidine Chemical compound C1=CC(Cl)=CC=C1C(C(=N1)C=2C=CC=CC=2)=NN1CCCN1CCCCC1 RXLFBOFHZJXGRZ-UHFFFAOYSA-N 0.000 claims abstract 2
- SMIIMABNEHRULZ-UHFFFAOYSA-N 4-[3-[4-(2,4-dichlorophenyl)-5-(4-methylphenyl)triazol-2-yl]propyl]morpholine Chemical compound C1=CC(C)=CC=C1C(C(=N1)C=2C(=CC(Cl)=CC=2)Cl)=NN1CCCN1CCOCC1 SMIIMABNEHRULZ-UHFFFAOYSA-N 0.000 claims abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract 2
- 229910052801 chlorine Inorganic materials 0.000 claims abstract 2
- 239000000460 chlorine Substances 0.000 claims abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims abstract 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims abstract 2
- -1 [1,2,3] triazol-2-yl Chemical group 0.000 claims 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 6
- 208000004454 Hyperalgesia Diseases 0.000 claims 6
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims 6
- 201000010099 disease Diseases 0.000 claims 5
- 238000011282 treatment Methods 0.000 claims 5
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 4
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims 3
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 claims 3
- 208000019901 Anxiety disease Diseases 0.000 claims 3
- 208000023275 Autoimmune disease Diseases 0.000 claims 3
- 208000028698 Cognitive impairment Diseases 0.000 claims 3
- 208000016192 Demyelinating disease Diseases 0.000 claims 3
- 206010012735 Diarrhoea Diseases 0.000 claims 3
- 208000010412 Glaucoma Diseases 0.000 claims 3
- 206010019233 Headaches Diseases 0.000 claims 3
- 208000035150 Hypercholesterolemia Diseases 0.000 claims 3
- 208000035154 Hyperesthesia Diseases 0.000 claims 3
- 208000031226 Hyperlipidaemia Diseases 0.000 claims 3
- 206010020772 Hypertension Diseases 0.000 claims 3
- 206010065390 Inflammatory pain Diseases 0.000 claims 3
- 208000032382 Ischaemic stroke Diseases 0.000 claims 3
- 102000004895 Lipoproteins Human genes 0.000 claims 3
- 108090001030 Lipoproteins Proteins 0.000 claims 3
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 208000008589 Obesity Diseases 0.000 claims 3
- 208000002193 Pain Diseases 0.000 claims 3
- 208000006011 Stroke Diseases 0.000 claims 3
- 206010043118 Tardive Dyskinesia Diseases 0.000 claims 3
- 208000025865 Ulcer Diseases 0.000 claims 3
- 206010053552 allodynia Diseases 0.000 claims 3
- 229940025084 amphetamine Drugs 0.000 claims 3
- 230000036506 anxiety Effects 0.000 claims 3
- 206010003119 arrhythmia Diseases 0.000 claims 3
- 230000006793 arrhythmia Effects 0.000 claims 3
- 206010003246 arthritis Diseases 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 229960003920 cocaine Drugs 0.000 claims 3
- 208000010877 cognitive disease Diseases 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 206010013663 drug dependence Diseases 0.000 claims 3
- 206010015037 epilepsy Diseases 0.000 claims 3
- 229960004756 ethanol Drugs 0.000 claims 3
- 208000006575 hypertriglyceridemia Diseases 0.000 claims 3
- 208000027866 inflammatory disease Diseases 0.000 claims 3
- 230000002757 inflammatory effect Effects 0.000 claims 3
- 201000003723 learning disability Diseases 0.000 claims 3
- 208000004296 neuralgia Diseases 0.000 claims 3
- 208000021722 neuropathic pain Diseases 0.000 claims 3
- 229960002715 nicotine Drugs 0.000 claims 3
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims 3
- 235000020824 obesity Nutrition 0.000 claims 3
- 201000000980 schizophrenia Diseases 0.000 claims 3
- 239000000126 substance Substances 0.000 claims 3
- 231100000397 ulcer Toxicity 0.000 claims 3
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 2
- 238000005804 alkylation reaction Methods 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 230000004770 neurodegeneration Effects 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- QPHKZDGGFGGCDJ-UHFFFAOYSA-N 1-[2-(4-phenyltriazol-2-yl)ethyl]azepane Chemical compound C1CCCCCN1CCN(N=1)N=CC=1C1=CC=CC=C1 QPHKZDGGFGGCDJ-UHFFFAOYSA-N 0.000 claims 1
- QODYALOVHNCCKF-UHFFFAOYSA-N 1-[2-(4-phenyltriazol-2-yl)ethyl]piperidine Chemical compound C1CCCCN1CCN(N=1)N=CC=1C1=CC=CC=C1 QODYALOVHNCCKF-UHFFFAOYSA-N 0.000 claims 1
- GNNUFCDGSDJQPE-UHFFFAOYSA-N 1-[2-[4-(4-chlorophenyl)-5-phenyltriazol-2-yl]ethyl]piperidine Chemical compound C1=CC(Cl)=CC=C1C(C(=N1)C=2C=CC=CC=2)=NN1CCN1CCCCC1 GNNUFCDGSDJQPE-UHFFFAOYSA-N 0.000 claims 1
- FXECWAXRHRBMMG-UHFFFAOYSA-N 1-[3-(4-methyl-5-phenyltriazol-2-yl)propyl]piperidine Chemical compound N1=C(C=2C=CC=CC=2)C(C)=NN1CCCN1CCCCC1 FXECWAXRHRBMMG-UHFFFAOYSA-N 0.000 claims 1
- ZAOFUUGYVOBXKH-UHFFFAOYSA-N 1-[3-(4-phenyltriazol-2-yl)propyl]azepane Chemical compound N1=CC(C=2C=CC=CC=2)=NN1CCCN1CCCCCC1 ZAOFUUGYVOBXKH-UHFFFAOYSA-N 0.000 claims 1
- ZJCIOJGJGJKZBR-UHFFFAOYSA-N 1-[3-(4-phenyltriazol-2-yl)propyl]piperidine Chemical compound N1=CC(C=2C=CC=CC=2)=NN1CCCN1CCCCC1 ZJCIOJGJGJKZBR-UHFFFAOYSA-N 0.000 claims 1
- RXMSTAIWAPIJNB-UHFFFAOYSA-N 1-[3-[4-(4-bromo-2-fluorophenyl)triazol-2-yl]propyl]piperidine Chemical compound FC1=CC(Br)=CC=C1C1=NN(CCCN2CCCCC2)N=C1 RXMSTAIWAPIJNB-UHFFFAOYSA-N 0.000 claims 1
- VWKBXKVJNNHWBY-UHFFFAOYSA-N 1-[3-[4-(4-chlorophenyl)-5-phenyltriazol-2-yl]propyl]-4-phenylpiperazine Chemical compound C1=CC(Cl)=CC=C1C(C(=N1)C=2C=CC=CC=2)=NN1CCCN1CCN(C=2C=CC=CC=2)CC1 VWKBXKVJNNHWBY-UHFFFAOYSA-N 0.000 claims 1
- GNBYZIZVAFKIAD-UHFFFAOYSA-N 1-[3-[4-(4-chlorophenyl)-5-phenyltriazol-2-yl]propyl]-4-phenylpiperidine Chemical compound C1=CC(Cl)=CC=C1C(C(=N1)C=2C=CC=CC=2)=NN1CCCN1CCC(C=2C=CC=CC=2)CC1 GNBYZIZVAFKIAD-UHFFFAOYSA-N 0.000 claims 1
- RANJVMWCDJUSPP-UHFFFAOYSA-N 1-[4-(4-phenyltriazol-2-yl)butyl]azepane Chemical compound C1CCCCCN1CCCCN(N=1)N=CC=1C1=CC=CC=C1 RANJVMWCDJUSPP-UHFFFAOYSA-N 0.000 claims 1
- OWXBJIZYYYWPOK-UHFFFAOYSA-N 1-[4-[4-(4-chlorophenyl)-5-phenyltriazol-2-yl]butyl]piperidine Chemical compound C1=CC(Cl)=CC=C1C(C(=N1)C=2C=CC=CC=2)=NN1CCCCN1CCCCC1 OWXBJIZYYYWPOK-UHFFFAOYSA-N 0.000 claims 1
- SLLZNMBEIVMVOK-UHFFFAOYSA-N 1-[5-[4-(4-chlorophenyl)-5-phenyltriazol-2-yl]pentyl]piperidine Chemical compound C1=CC(Cl)=CC=C1C(C(=N1)C=2C=CC=CC=2)=NN1CCCCCN1CCCCC1 SLLZNMBEIVMVOK-UHFFFAOYSA-N 0.000 claims 1
- KNFJJWWYDSKJKZ-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-phenyl-2-(3-pyrrolidin-1-ylpropyl)triazole Chemical compound C1=CC(Cl)=CC=C1C(C(=N1)C=2C=CC=CC=2)=NN1CCCN1CCCC1 KNFJJWWYDSKJKZ-UHFFFAOYSA-N 0.000 claims 1
- PDHJSTSIOUMGPN-UHFFFAOYSA-N 4-[2-[4-(4-chlorophenyl)-5-phenyltriazol-2-yl]ethyl]morpholine Chemical compound C1=CC(Cl)=CC=C1C(C(=N1)C=2C=CC=CC=2)=NN1CCN1CCOCC1 PDHJSTSIOUMGPN-UHFFFAOYSA-N 0.000 claims 1
- MLVGRNXYOQCXIV-UHFFFAOYSA-N 4-[3-(4-phenyltriazol-2-yl)propyl]morpholine Chemical compound N1=CC(C=2C=CC=CC=2)=NN1CCCN1CCOCC1 MLVGRNXYOQCXIV-UHFFFAOYSA-N 0.000 claims 1
- CKRUXDNBPZPWFQ-UHFFFAOYSA-N 4-[3-[4-(4-chlorophenyl)-5-phenyltriazol-2-yl]propyl]morpholine Chemical compound C1=CC(Cl)=CC=C1C(C(=N1)C=2C=CC=CC=2)=NN1CCCN1CCOCC1 CKRUXDNBPZPWFQ-UHFFFAOYSA-N 0.000 claims 1
- 102100028656 Sigma non-opioid intracellular receptor 1 Human genes 0.000 claims 1
- 101710104750 Sigma non-opioid intracellular receptor 1 Proteins 0.000 claims 1
- 230000029936 alkylation Effects 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 239000002249 anxiolytic agent Substances 0.000 claims 1
- 230000000949 anxiolytic effect Effects 0.000 claims 1
- 238000006352 cycloaddition reaction Methods 0.000 claims 1
- CGTZBPXNCBEGCF-UHFFFAOYSA-N cyclohexyl-[3-(4-phenyltriazol-2-yl)propyl]azanium;oxalate Chemical compound [O-]C(=O)C([O-])=O.N1=CC(C=2C=CC=CC=2)=NN1CCC[NH2+]C1CCCCC1.N1=CC(C=2C=CC=CC=2)=NN1CCC[NH2+]C1CCCCC1 CGTZBPXNCBEGCF-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229960003444 immunosuppressant agent Drugs 0.000 claims 1
- 230000001861 immunosuppressant effect Effects 0.000 claims 1
- 239000003018 immunosuppressive agent Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 239000002609 medium Substances 0.000 claims 1
- 235000006408 oxalic acid Nutrition 0.000 claims 1
- 230000001575 pathological effect Effects 0.000 claims 1
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- 239000002831 pharmacologic agent Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
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- JKVRTUCVPZTEQZ-UHFFFAOYSA-N tributyltin azide Chemical compound CCCC[Sn](CCCC)(CCCC)N=[N+]=[N-] JKVRTUCVPZTEQZ-UHFFFAOYSA-N 0.000 claims 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
- C07D249/06—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles with aryl radicals directly attached to ring atoms
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- 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
- A61K31/4192—1,2,3-Triazoles
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- A61P9/12—Antihypertensives
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Addiction (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Immunology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Rheumatology (AREA)
- Ophthalmology & Optometry (AREA)
- Obesity (AREA)
- Child & Adolescent Psychology (AREA)
- Urology & Nephrology (AREA)
- Transplantation (AREA)
- Hospice & Palliative Care (AREA)
- Vascular Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP06380289A EP1921071A1 (en) | 2006-11-10 | 2006-11-10 | 1,2,3- triazole derivatives as sigma receptor inhibitors |
| EP06380289.6 | 2006-11-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2009122198A true RU2009122198A (ru) | 2010-12-20 |
Family
ID=37963991
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2009122198/04A RU2009122198A (ru) | 2006-11-10 | 2007-11-07 | Производные 1,2,3-триазола в качестве ингибиторов сигма-рецепторов |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US8193223B2 (enExample) |
| EP (2) | EP1921071A1 (enExample) |
| JP (1) | JP2010509281A (enExample) |
| KR (1) | KR20090087032A (enExample) |
| CN (1) | CN101589029A (enExample) |
| AU (1) | AU2007316606A1 (enExample) |
| BR (1) | BRPI0718586A2 (enExample) |
| CA (1) | CA2668996A1 (enExample) |
| ES (1) | ES2413559T3 (enExample) |
| MX (1) | MX2009004745A (enExample) |
| RU (1) | RU2009122198A (enExample) |
| WO (1) | WO2008055933A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2666728C2 (ru) * | 2013-04-19 | 2018-09-12 | Лабораториос Дель Др. Эстеве, С.А. | Трициклические триазольные соединения |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2116539A1 (en) | 2008-04-25 | 2009-11-11 | Laboratorios Del. Dr. Esteve, S.A. | 1-aryl-3-aminoalkoxy-pyrazoles as sigma ligands enhancing analgesic effects of opioids and attenuating the dependency thereof |
| EP2353591A1 (en) | 2010-02-04 | 2011-08-10 | Laboratorios Del. Dr. Esteve, S.A. | Sigma ligands for potentiating the analgesic effect of opioids and opiates in post-operative pain and attenuating the dependency thereof |
| EP2388005A1 (en) | 2010-05-21 | 2011-11-23 | Laboratorios Del. Dr. Esteve, S.A. | Sigma ligands for the prevention and/or treatment of emesis induced by chemotherapy or radiotherapy |
| EP2395003A1 (en) | 2010-05-27 | 2011-12-14 | Laboratorios Del. Dr. Esteve, S.A. | Pyrazole compounds as sigma receptor inhibitors |
| EP2415471A1 (en) | 2010-08-03 | 2012-02-08 | Laboratorios Del. Dr. Esteve, S.A. | Use of sigma ligands in opioid-induced hyperalgesia |
| EP2524694A1 (en) | 2011-05-19 | 2012-11-21 | Laboratorios Del. Dr. Esteve, S.A. | Use of sigma ligands in diabetes type-2 associated pain |
| EP2548878A1 (en) * | 2011-07-21 | 2013-01-23 | Laboratorios Del. Dr. Esteve, S.A. | Pyrazolo[3,4-d]pyrimidine compounds, their preparation and use as sigma ligands |
| EP2567959B1 (en) | 2011-09-12 | 2014-04-16 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| EP2752411A1 (en) * | 2013-01-07 | 2014-07-09 | Laboratorios Del Dr. Esteve, S.A. | 1,2,3-triazole-4-amine derivatives for the treatment of sigma receptor related diseases and disorders |
| US9879015B2 (en) | 2013-04-23 | 2018-01-30 | Laboratorios Del Dr. Esteve S.A. | Pyrazino[1,2-a]indole compounds, their preparation and use in medicaments |
| CA2909924A1 (en) | 2013-04-23 | 2014-10-30 | Laboratorios Del Dr. Esteve, S.A. | Pyrazino[1,2-a]indole compounds, their preparation and use in medicaments |
| EP2832720A1 (en) | 2013-07-30 | 2015-02-04 | Laboratorios Del. Dr. Esteve, S.A. | 1,2-disubstituted cyclobutyl compounds |
| SG11201604480PA (en) | 2013-12-17 | 2016-07-28 | Esteve Labor Dr | SEROTONIN-NOREPINEPHRINE REUPTAKE INHIBITORS (SNRIs) AND SIGMA RECEPTOR LIGANDS COMBINATIONS |
| MA41177A (fr) * | 2014-12-15 | 2017-10-24 | Esteve Labor Dr | Utilisation de ligands des récepteurs sigma dans l'arthrose |
| PT3250563T (pt) * | 2015-01-30 | 2022-02-09 | Neurocrine Biosciences Inc | Triazois substituídos e métodos relacionados aos mesmos |
| CN106866555B (zh) * | 2017-02-08 | 2019-04-30 | 东南大学 | 1-二苯甲基-4-甲基哌嗪类化合物其制备方法和应用 |
| EP3893892A4 (en) * | 2018-12-12 | 2022-09-14 | Rutgers, the State University of New Jersey | ORGANIC COMPOUNDS |
| CN116178286B (zh) * | 2021-11-26 | 2024-12-03 | 华东师范大学 | 一种n2烷基取代的三氮唑衍生物及其合成方法与应用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2071897A1 (en) | 1989-12-28 | 1991-06-29 | Richard A. Glennon | Sigma receptor ligands and the use thereof |
| WO2002036119A1 (en) * | 2000-11-02 | 2002-05-10 | K And K Biosciences, Inc. | Δ2,-1,2,3-triazoline anticonvulsants and their active metabolite analogues, the aminoalkylpyridines, are excitatory amino acid antagonists and antiischemic agents, useful in the treatment of cerebral ischemia resulting from stroke |
| AU2006311786A1 (en) * | 2005-11-04 | 2007-05-18 | Merck Sharp & Dohme Corp. | Diphenylmethane derivatives as inhibitors of leukotriene biosynthesis |
-
2006
- 2006-11-10 EP EP06380289A patent/EP1921071A1/en not_active Withdrawn
-
2007
- 2007-11-07 BR BRPI0718586-3A2A patent/BRPI0718586A2/pt not_active Application Discontinuation
- 2007-11-07 AU AU2007316606A patent/AU2007316606A1/en not_active Abandoned
- 2007-11-07 WO PCT/EP2007/062010 patent/WO2008055933A1/en not_active Ceased
- 2007-11-07 MX MX2009004745A patent/MX2009004745A/es not_active Application Discontinuation
- 2007-11-07 EP EP07822321A patent/EP2097392B1/en not_active Not-in-force
- 2007-11-07 KR KR1020097011468A patent/KR20090087032A/ko not_active Withdrawn
- 2007-11-07 CN CNA2007800418260A patent/CN101589029A/zh active Pending
- 2007-11-07 CA CA002668996A patent/CA2668996A1/en not_active Abandoned
- 2007-11-07 JP JP2009535724A patent/JP2010509281A/ja active Pending
- 2007-11-07 ES ES07822321T patent/ES2413559T3/es active Active
- 2007-11-07 RU RU2009122198/04A patent/RU2009122198A/ru not_active Application Discontinuation
- 2007-11-07 US US12/514,213 patent/US8193223B2/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2666728C2 (ru) * | 2013-04-19 | 2018-09-12 | Лабораториос Дель Др. Эстеве, С.А. | Трициклические триазольные соединения |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20090087032A (ko) | 2009-08-14 |
| BRPI0718586A2 (pt) | 2014-03-11 |
| MX2009004745A (es) | 2009-05-22 |
| EP2097392A1 (en) | 2009-09-09 |
| CN101589029A (zh) | 2009-11-25 |
| AU2007316606A1 (en) | 2008-05-15 |
| US8193223B2 (en) | 2012-06-05 |
| ES2413559T3 (es) | 2013-07-16 |
| EP1921071A1 (en) | 2008-05-14 |
| WO2008055933A1 (en) | 2008-05-15 |
| CA2668996A1 (en) | 2008-05-15 |
| US20100004265A1 (en) | 2010-01-07 |
| JP2010509281A (ja) | 2010-03-25 |
| EP2097392B1 (en) | 2013-03-13 |
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Legal Events
| Date | Code | Title | Description |
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| FA93 | Acknowledgement of application withdrawn (no request for examination) |
Effective date: 20110311 |