RU2010102994A - Новые производные 1,2,3-триазола, полезные в качестве модуляторов никотиновых ацетилхолиновых рецепторов - Google Patents
Новые производные 1,2,3-триазола, полезные в качестве модуляторов никотиновых ацетилхолиновых рецепторов Download PDFInfo
- Publication number
- RU2010102994A RU2010102994A RU2010102994/04A RU2010102994A RU2010102994A RU 2010102994 A RU2010102994 A RU 2010102994A RU 2010102994/04 A RU2010102994/04 A RU 2010102994/04A RU 2010102994 A RU2010102994 A RU 2010102994A RU 2010102994 A RU2010102994 A RU 2010102994A
- Authority
- RU
- Russia
- Prior art keywords
- triazol
- ylamine
- trifluoromethylphenyl
- methoxyphenyl
- amino
- Prior art date
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- 150000000177 1,2,3-triazoles Chemical class 0.000 title claims 9
- 108010009685 Cholinergic Receptors Proteins 0.000 title 1
- 102000034337 acetylcholine receptors Human genes 0.000 title 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Chemical compound CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract 13
- 239000000203 mixture Substances 0.000 claims abstract 11
- -1 hydroxy, amino Chemical group 0.000 claims abstract 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 8
- 239000001257 hydrogen Substances 0.000 claims abstract 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract 4
- 125000003118 aryl group Chemical group 0.000 claims abstract 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 4
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 4
- 150000002431 hydrogen Chemical group 0.000 claims abstract 4
- 125000001715 oxadiazolyl group Chemical group 0.000 claims abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 4
- 125000001424 substituent group Chemical group 0.000 claims abstract 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims abstract 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract 2
- 125000001475 halogen functional group Chemical group 0.000 claims abstract 2
- 150000002367 halogens Chemical class 0.000 claims abstract 2
- 208000002193 Pain Diseases 0.000 claims 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 8
- 208000035475 disorder Diseases 0.000 claims 5
- 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 claims 3
- 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 claims 3
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims 3
- 206010048010 Withdrawal syndrome Diseases 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000004296 neuralgia Diseases 0.000 claims 3
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 2
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 2
- 206010010904 Convulsion Diseases 0.000 claims 2
- 206010012735 Diarrhoea Diseases 0.000 claims 2
- 208000026097 Factitious disease Diseases 0.000 claims 2
- 206010020651 Hyperkinesia Diseases 0.000 claims 2
- 208000000269 Hyperkinesis Diseases 0.000 claims 2
- 241001465754 Metazoa Species 0.000 claims 2
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims 2
- 206010043118 Tardive Dyskinesia Diseases 0.000 claims 2
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 2
- 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 2
- 206010015037 epilepsy Diseases 0.000 claims 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims 2
- 208000021722 neuropathic pain Diseases 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 208000024891 symptom Diseases 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims 1
- BVSRMHRPTLJGNR-UHFFFAOYSA-N 2-[5-amino-1-(2,4-dichlorophenyl)triazol-4-yl]-4-chlorophenol Chemical compound NC1=C(C=2C(=CC=C(Cl)C=2)O)N=NN1C1=CC=C(Cl)C=C1Cl BVSRMHRPTLJGNR-UHFFFAOYSA-N 0.000 claims 1
- HJRWKGXLCYRXAS-UHFFFAOYSA-N 2-[5-amino-1-[2-chloro-4-(trifluoromethyl)phenyl]triazol-4-yl]-4-chlorophenol Chemical compound NC1=C(C=2C(=CC=C(Cl)C=2)O)N=NN1C1=CC=C(C(F)(F)F)C=C1Cl HJRWKGXLCYRXAS-UHFFFAOYSA-N 0.000 claims 1
- KZRHIVZDKQVNPN-UHFFFAOYSA-N 3-(2,4-dichloro-6-iodophenyl)-5-(4-methoxyphenyl)triazol-4-amine Chemical compound C1=CC(OC)=CC=C1C1=C(N)N(C=2C(=CC(Cl)=CC=2Cl)I)N=N1 KZRHIVZDKQVNPN-UHFFFAOYSA-N 0.000 claims 1
- YLZARLJSOWWBNL-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-5-(4-methoxyphenyl)triazol-4-amine Chemical compound C1=CC(OC)=CC=C1C1=C(N)N(C=2C(=CC(Cl)=CC=2)Cl)N=N1 YLZARLJSOWWBNL-UHFFFAOYSA-N 0.000 claims 1
- PEVDEGICNXHSSE-UHFFFAOYSA-N 3-(2-chloro-4-fluorophenyl)-5-(4-methoxyphenyl)triazol-4-amine Chemical compound C1=CC(OC)=CC=C1C1=C(N)N(C=2C(=CC(F)=CC=2)Cl)N=N1 PEVDEGICNXHSSE-UHFFFAOYSA-N 0.000 claims 1
- CJVBYZFANMMHHM-UHFFFAOYSA-N 3-[2-chloro-4-(trifluoromethyl)phenyl]-5-(4-methoxyphenyl)triazol-4-amine Chemical compound C1=CC(OC)=CC=C1C1=C(N)N(C=2C(=CC(=CC=2)C(F)(F)F)Cl)N=N1 CJVBYZFANMMHHM-UHFFFAOYSA-N 0.000 claims 1
- UUDQBGQGDILMHA-UHFFFAOYSA-N 3-[2-fluoro-4-(trifluoromethyl)phenyl]-5-(4-methoxyphenyl)triazol-4-amine Chemical compound C1=CC(OC)=CC=C1C1=C(N)N(C=2C(=CC(=CC=2)C(F)(F)F)F)N=N1 UUDQBGQGDILMHA-UHFFFAOYSA-N 0.000 claims 1
- LAYHRUYVNMGPET-UHFFFAOYSA-N 3-[2-fluoro-4-(trifluoromethyl)phenyl]-5-[4-(trifluoromethoxy)phenyl]triazol-4-amine Chemical compound NC1=C(C=2C=CC(OC(F)(F)F)=CC=2)N=NN1C1=CC=C(C(F)(F)F)C=C1F LAYHRUYVNMGPET-UHFFFAOYSA-N 0.000 claims 1
- YQQSSRXWYNOVBN-UHFFFAOYSA-N 4-[5-amino-1-(2,4-dichlorophenyl)triazol-4-yl]benzonitrile Chemical compound NC1=C(C=2C=CC(=CC=2)C#N)N=NN1C1=CC=C(Cl)C=C1Cl YQQSSRXWYNOVBN-UHFFFAOYSA-N 0.000 claims 1
- NPKRWBUJWKXGHT-UHFFFAOYSA-N 4-[5-amino-1-[2-chloro-4-(trifluoromethyl)phenyl]triazol-4-yl]phenol Chemical compound NC1=C(C=2C=CC(O)=CC=2)N=NN1C1=CC=C(C(F)(F)F)C=C1Cl NPKRWBUJWKXGHT-UHFFFAOYSA-N 0.000 claims 1
- RITFOWIQAQDPRO-UHFFFAOYSA-N 4-[5-amino-1-[2-fluoro-4-(trifluoromethyl)phenyl]triazol-4-yl]phenol Chemical compound NC1=C(C=2C=CC(O)=CC=2)N=NN1C1=CC=C(C(F)(F)F)C=C1F RITFOWIQAQDPRO-UHFFFAOYSA-N 0.000 claims 1
- HWAWIIPRNMFJMI-UHFFFAOYSA-N 4-[5-amino-4-[2-fluoro-4-(trifluoromethyl)phenyl]triazol-1-yl]benzenesulfonamide Chemical compound NC1=C(C=2C(=CC(=CC=2)C(F)(F)F)F)N=NN1C1=CC=C(S(N)(=O)=O)C=C1 HWAWIIPRNMFJMI-UHFFFAOYSA-N 0.000 claims 1
- HELKOFBFKICWNT-UHFFFAOYSA-N 4-[5-amino-4-[2-fluoro-4-(trifluoromethyl)phenyl]triazol-1-yl]phenol Chemical compound NC1=C(C=2C(=CC(=CC=2)C(F)(F)F)F)N=NN1C1=CC=C(O)C=C1 HELKOFBFKICWNT-UHFFFAOYSA-N 0.000 claims 1
- ZMRVSZFBDDJUMQ-UHFFFAOYSA-N 5-(2,4-dichlorophenyl)-3-(4-methoxyphenyl)triazol-4-amine Chemical compound C1=CC(OC)=CC=C1N1C(N)=C(C=2C(=CC(Cl)=CC=2)Cl)N=N1 ZMRVSZFBDDJUMQ-UHFFFAOYSA-N 0.000 claims 1
- XWFJEDOALHUHHM-UHFFFAOYSA-N 5-(2,4-difluorophenyl)-3-(4-methoxyphenyl)triazol-4-amine Chemical compound C1=CC(OC)=CC=C1N1C(N)=C(C=2C(=CC(F)=CC=2)F)N=N1 XWFJEDOALHUHHM-UHFFFAOYSA-N 0.000 claims 1
- ZDKRGWXNZRXQJP-UHFFFAOYSA-N 5-(2-chloro-4-fluorophenyl)-3-(4-methoxyphenyl)triazol-4-amine Chemical compound C1=CC(OC)=CC=C1N1C(N)=C(C=2C(=CC(F)=CC=2)Cl)N=N1 ZDKRGWXNZRXQJP-UHFFFAOYSA-N 0.000 claims 1
- FIYUJUMRDKTMKE-UHFFFAOYSA-N 5-(3,4-dichlorophenyl)-3-(4-methoxyphenyl)triazol-4-amine Chemical compound C1=CC(OC)=CC=C1N1C(N)=C(C=2C=C(Cl)C(Cl)=CC=2)N=N1 FIYUJUMRDKTMKE-UHFFFAOYSA-N 0.000 claims 1
- MSJMTNCXWPPVAT-UHFFFAOYSA-N 5-(4-aminophenyl)-3-[2-fluoro-4-(trifluoromethyl)phenyl]triazol-4-amine Chemical compound NC1=C(C=2C=CC(N)=CC=2)N=NN1C1=CC=C(C(F)(F)F)C=C1F MSJMTNCXWPPVAT-UHFFFAOYSA-N 0.000 claims 1
- NAXPHDYTHWICLV-UHFFFAOYSA-N 5-(4-chloro-2-fluorophenyl)-3-(4-methoxyphenyl)triazol-4-amine Chemical compound C1=CC(OC)=CC=C1N1C(N)=C(C=2C(=CC(Cl)=CC=2)F)N=N1 NAXPHDYTHWICLV-UHFFFAOYSA-N 0.000 claims 1
- JWXNCOWZOAWVOO-UHFFFAOYSA-N 5-(4-chlorophenyl)-3-[2-fluoro-4-(trifluoromethyl)phenyl]triazol-4-amine Chemical compound NC1=C(C=2C=CC(Cl)=CC=2)N=NN1C1=CC=C(C(F)(F)F)C=C1F JWXNCOWZOAWVOO-UHFFFAOYSA-N 0.000 claims 1
- ZWAJMZFSHJRPTF-UHFFFAOYSA-N 5-(4-methoxyphenyl)-3-(5-methyl-1,2-oxazol-3-yl)triazol-4-amine Chemical compound C1=CC(OC)=CC=C1C1=C(N)N(C2=NOC(C)=C2)N=N1 ZWAJMZFSHJRPTF-UHFFFAOYSA-N 0.000 claims 1
- SJJAODBZRZXEGS-UHFFFAOYSA-N 5-(5-chloro-2-methoxyphenyl)-3-(2,4-dichlorophenyl)triazol-4-amine Chemical compound COC1=CC=C(Cl)C=C1C1=C(N)N(C=2C(=CC(Cl)=CC=2)Cl)N=N1 SJJAODBZRZXEGS-UHFFFAOYSA-N 0.000 claims 1
- SRQGIQKNDGUPDC-UHFFFAOYSA-N 5-(5-chloro-2-methoxyphenyl)-3-[2-chloro-4-(trifluoromethyl)phenyl]triazol-4-amine Chemical compound COC1=CC=C(Cl)C=C1C1=C(N)N(C=2C(=CC(=CC=2)C(F)(F)F)Cl)N=N1 SRQGIQKNDGUPDC-UHFFFAOYSA-N 0.000 claims 1
- KIFSHCNOJWCTCK-UHFFFAOYSA-N 5-[2-fluoro-4-(trifluoromethyl)phenyl]-3-(4-methoxyphenyl)triazol-4-amine Chemical compound C1=CC(OC)=CC=C1N1C(N)=C(C=2C(=CC(=CC=2)C(F)(F)F)F)N=N1 KIFSHCNOJWCTCK-UHFFFAOYSA-N 0.000 claims 1
- YYTRPIAXOVEEDQ-UHFFFAOYSA-N 5-[4-chloro-2-(trifluoromethyl)phenyl]-3-(4-methoxyphenyl)triazol-4-amine Chemical compound C1=CC(OC)=CC=C1N1C(N)=C(C=2C(=CC(Cl)=CC=2)C(F)(F)F)N=N1 YYTRPIAXOVEEDQ-UHFFFAOYSA-N 0.000 claims 1
- 208000030507 AIDS Diseases 0.000 claims 1
- 208000002874 Acne Vulgaris Diseases 0.000 claims 1
- 206010002383 Angina Pectoris Diseases 0.000 claims 1
- 208000000103 Anorexia Nervosa Diseases 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 206010003805 Autism Diseases 0.000 claims 1
- 208000020706 Autistic disease Diseases 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- 208000032841 Bulimia Diseases 0.000 claims 1
- 206010006550 Bulimia nervosa Diseases 0.000 claims 1
- 206010008874 Chronic Fatigue Syndrome Diseases 0.000 claims 1
- 208000000094 Chronic Pain Diseases 0.000 claims 1
- 208000028698 Cognitive impairment Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 206010012289 Dementia Diseases 0.000 claims 1
- 201000004624 Dermatitis Diseases 0.000 claims 1
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims 1
- 208000030814 Eating disease Diseases 0.000 claims 1
- 208000010228 Erectile Dysfunction Diseases 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 1
- 206010019233 Headaches Diseases 0.000 claims 1
- GVGLGOZIDCSQPN-PVHGPHFFSA-N Heroin Chemical compound O([C@H]1[C@H](C=C[C@H]23)OC(C)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4OC(C)=O GVGLGOZIDCSQPN-PVHGPHFFSA-N 0.000 claims 1
- 208000023105 Huntington disease Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 206010020850 Hyperthyroidism Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 206010026749 Mania Diseases 0.000 claims 1
- 208000019695 Migraine disease Diseases 0.000 claims 1
- 206010028403 Mutism Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
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- 208000005107 Premature Birth Diseases 0.000 claims 1
- 206010036590 Premature baby Diseases 0.000 claims 1
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- 206010052276 Pseudodementia Diseases 0.000 claims 1
- 208000028017 Psychotic disease Diseases 0.000 claims 1
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- 206010003119 arrhythmia Diseases 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 229940049706 benzodiazepine Drugs 0.000 claims 1
- 150000001557 benzodiazepines Chemical class 0.000 claims 1
- 208000028683 bipolar I disease Diseases 0.000 claims 1
- 229960003920 cocaine Drugs 0.000 claims 1
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- 230000008602 contraction Effects 0.000 claims 1
- 230000036461 convulsion Effects 0.000 claims 1
- 229960002069 diamorphine Drugs 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 235000014632 disordered eating Nutrition 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000004064 dysfunction Effects 0.000 claims 1
- 206010013932 dyslexia Diseases 0.000 claims 1
- 208000030172 endocrine system disease Diseases 0.000 claims 1
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- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims 1
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- 201000003723 learning disability Diseases 0.000 claims 1
- 230000029849 luteinization Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 206010027175 memory impairment Diseases 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
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- 229960005181 morphine Drugs 0.000 claims 1
- 208000029766 myalgic encephalomeyelitis/chronic fatigue syndrome Diseases 0.000 claims 1
- YEZGCZLZALVFGW-UHFFFAOYSA-N n-[4-[5-amino-1-[2-fluoro-4-(trifluoromethyl)phenyl]triazol-4-yl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=C(N)N(C=2C(=CC(=CC=2)C(F)(F)F)F)N=N1 YEZGCZLZALVFGW-UHFFFAOYSA-N 0.000 claims 1
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- 125000001399 1,2,3-triazolyl group Chemical class N1N=NC(=C1)* 0.000 abstract 5
Classifications
-
- 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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- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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Applications Claiming Priority (4)
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| DKPA200701134 | 2007-08-08 | ||
| DKPA200701134 | 2007-08-08 | ||
| US95508107P | 2007-08-10 | 2007-08-10 | |
| US60/955,081 | 2007-08-10 |
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| RU2010102994A true RU2010102994A (ru) | 2011-09-20 |
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| EP (1) | EP2185529A1 (enExample) |
| JP (1) | JP2010535738A (enExample) |
| KR (1) | KR20100046179A (enExample) |
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| RU (1) | RU2010102994A (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2009112459A1 (en) * | 2008-03-11 | 2009-09-17 | Neurosearch A/S | Novel 1,2,3-triazole derivatives useful as modulators of nicotinic acetylcholine receptors |
| CA2733499A1 (en) * | 2008-08-08 | 2010-02-11 | Neurosearch A/S | Novel diphenyl 1,2,3-triazole derivatives useful as modulators of nicotinic acetylcholine receptors |
| AU2009289329A1 (en) * | 2008-09-02 | 2010-03-11 | Neurosearch A/S | Triazole derivatives and their use as nicotinic acetylcholine receptor modulators |
| TW201124409A (en) | 2009-10-07 | 2011-07-16 | Karobio Ab | Novel estrogen receptor ligands |
| US20130310419A1 (en) | 2011-02-03 | 2013-11-21 | Lupin Limited | Pyrrole derivatives used as modulators of alpha7 nachr |
| MA34957B1 (fr) | 2011-02-23 | 2014-03-01 | Lupin Ltd | Derives heteroaryle a titre modulateurs des nachr alpha 7 |
| EP2691368A1 (en) | 2011-03-31 | 2014-02-05 | Lupin Limited | Pyrrole derivatives as nicotinic acetylcholine receptor modulators for use in the treatment of neurodegenerative disorders such as alzheimer's and parkinson's disease |
| FR2974365B1 (fr) * | 2011-04-20 | 2017-08-25 | Centre Nat De La Rech Scient (C N R S) | 1,2,3-triazoles 1,4-disubstituees, leurs procedes de preparation et leurs utilisations diagnostiques et therapeutiques |
| US8946432B2 (en) | 2011-07-05 | 2015-02-03 | Lupin Limited | Biaryl derivatives as nAChR modulators |
| GB201113538D0 (en) | 2011-08-04 | 2011-09-21 | Karobio Ab | Novel estrogen receptor ligands |
| EP2822946A1 (en) | 2012-03-06 | 2015-01-14 | Lupin Limited | Thiazole derivatives as alpha 7 nachr modulators |
| EP2945936A1 (en) | 2012-11-12 | 2015-11-25 | Lupin Limited | Thiazole derivatives as alpha 7 nachr modulators |
| EP2945941B1 (en) | 2013-01-16 | 2016-12-07 | Lupin Limited | Pyrrole derivatives as alpha 7 nachr modulators |
| JP2016512225A (ja) | 2013-03-13 | 2016-04-25 | ルピン・リミテッドＬｕｐｉｎ Ｌｉｍｉｔｅｄ | アルファー７ｎａｃｈｒモジュレータとしてのピロール誘導体 |
| TW201446243A (zh) | 2013-06-03 | 2014-12-16 | Lupin Ltd | 4-(5-(4-氯苯基)-2-(2-環丙基乙醯基)-1,4-二甲基-1氫-吡咯-3-基)苯磺醯胺作為α7尼古丁乙醯膽鹼受體調節劑 |
| AU2014282886A1 (en) | 2013-06-17 | 2015-12-17 | Lupin Limited | Pyrrole derivatives as alpha 7 nAChR modulators |
| WO2019124577A1 (ko) | 2017-12-20 | 2019-06-27 | 재단법인 경기도경제과학진흥원 | 트리아졸 유도체 및 이의 용도 |
| CN113045507B (zh) * | 2021-03-04 | 2022-10-25 | 中山大学南方学院 | 一种3,4-二羟基苯甲酸甲酯衍生物及其制备方法与应用 |
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| DE1242216B (de) * | 1963-12-27 | 1967-06-15 | Union Carbide Corp | Verfahren zur Herstellung von Inaminsalzen |
| JP4299139B2 (ja) * | 2001-12-18 | 2009-07-22 | メルク エンド カムパニー インコーポレーテッド | 代謝型グルタミン酸受容体−５のヘテロアリール置換トリアゾールモジュレータ |
| MXPA04010622A (es) * | 2002-04-26 | 2005-01-25 | Lilly Co Eli | Derivados de triazol como antagonistas de receptor de taquicinina. |
| US7825278B2 (en) | 2004-05-06 | 2010-11-02 | The Regents Of The University Of California | Substituted enaminones, their derivatives and uses thereof |
| WO2006071184A1 (en) | 2004-12-28 | 2006-07-06 | Astrazeneca Ab | Aryl sulphonamide modulators |
| WO2009112459A1 (en) | 2008-03-11 | 2009-09-17 | Neurosearch A/S | Novel 1,2,3-triazole derivatives useful as modulators of nicotinic acetylcholine receptors |
| CA2733499A1 (en) | 2008-08-08 | 2010-02-11 | Neurosearch A/S | Novel diphenyl 1,2,3-triazole derivatives useful as modulators of nicotinic acetylcholine receptors |
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2008
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Also Published As
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| CA2695812A1 (en) | 2009-02-12 |
| MX2010001135A (es) | 2010-03-09 |
| AU2008285644A1 (en) | 2009-02-12 |
| ZA201000127B (en) | 2011-03-30 |
| US20100222398A1 (en) | 2010-09-02 |
| EP2185529A1 (en) | 2010-05-19 |
| JP2010535738A (ja) | 2010-11-25 |
| US8110588B2 (en) | 2012-02-07 |
| NZ582520A (en) | 2011-10-28 |
| WO2009019278A1 (en) | 2009-02-12 |
| CN101796034A (zh) | 2010-08-04 |
| KR20100046179A (ko) | 2010-05-06 |
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| FA92 | Acknowledgement of application withdrawn (lack of supplementary materials submitted) |
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