RU2007139255A - Новые оксадиазольные производные и их медицинское применение - Google Patents
Новые оксадиазольные производные и их медицинское применение Download PDFInfo
- Publication number
- RU2007139255A RU2007139255A RU2007139255/04A RU2007139255A RU2007139255A RU 2007139255 A RU2007139255 A RU 2007139255A RU 2007139255/04 A RU2007139255/04 A RU 2007139255/04A RU 2007139255 A RU2007139255 A RU 2007139255A RU 2007139255 A RU2007139255 A RU 2007139255A
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- RU
- Russia
- Prior art keywords
- oxadiazol
- nitro
- phenyl
- pyridine
- cycloalkyl
- Prior art date
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- 150000004866 oxadiazoles Chemical class 0.000 title claims abstract 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract 14
- 208000002193 Pain Diseases 0.000 claims abstract 8
- 230000036407 pain Effects 0.000 claims abstract 8
- 201000010099 disease Diseases 0.000 claims abstract 7
- 208000035475 disorder Diseases 0.000 claims abstract 7
- 206010061218 Inflammation Diseases 0.000 claims abstract 2
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims abstract 2
- 230000004054 inflammatory process Effects 0.000 claims abstract 2
- 230000004770 neurodegeneration Effects 0.000 claims abstract 2
- 230000016160 smooth muscle contraction Effects 0.000 claims abstract 2
- 239000000126 substance Substances 0.000 claims abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 26
- -1 5-nitro-furan-2-yl Chemical group 0.000 claims 23
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims 10
- 125000001188 haloalkyl group Chemical group 0.000 claims 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 10
- 125000000217 alkyl group Chemical group 0.000 claims 9
- 125000002541 furyl group Chemical group 0.000 claims 9
- 125000001544 thienyl group Chemical group 0.000 claims 9
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 125000004438 haloalkoxy group Chemical group 0.000 claims 8
- 125000004076 pyridyl group Chemical group 0.000 claims 8
- 125000001424 substituent group Chemical group 0.000 claims 8
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 125000005843 halogen group Chemical group 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 5
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 5
- 125000003373 pyrazinyl group Chemical group 0.000 claims 5
- 208000002874 Acne Vulgaris Diseases 0.000 claims 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 4
- 206010000496 acne Diseases 0.000 claims 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims 3
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000000335 thiazolyl group Chemical group 0.000 claims 3
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- 208000020925 Bipolar disease Diseases 0.000 claims 2
- 208000032841 Bulimia Diseases 0.000 claims 2
- 206010006550 Bulimia nervosa Diseases 0.000 claims 2
- 108010009685 Cholinergic Receptors Proteins 0.000 claims 2
- 206010010904 Convulsion Diseases 0.000 claims 2
- 208000032131 Diabetic Neuropathies 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
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 2
- 206010043118 Tardive Dyskinesia Diseases 0.000 claims 2
- 102000034337 acetylcholine receptors Human genes 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 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
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 230000006735 deficit Effects 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 125000001620 monocyclic carbocycle group Chemical group 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
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims 2
- 208000004296 neuralgia Diseases 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 208000024891 symptom Diseases 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims 1
- BTJWQMQHCORTED-MBKKHDIZSA-N (4r)-4-[(7z,8r,9s,10s,13r,14s,17r)-3-hydroxy-7-hydroxyimino-10,13-dimethyl-1,2,3,4,5,6,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pentanoic acid Chemical compound C1CC(O)CC2C\C(=N\O)[C@H]3[C@@H]4CC[C@H]([C@@H](CCC(O)=O)C)[C@@]4(C)CC[C@@H]3[C@]21C BTJWQMQHCORTED-MBKKHDIZSA-N 0.000 claims 1
- FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 claims 1
- YXDXXGXWFJCXEB-UHFFFAOYSA-N 2-furonitrile Chemical compound N#CC1=CC=CO1 YXDXXGXWFJCXEB-UHFFFAOYSA-N 0.000 claims 1
- ZMUQWPUQGDJPSL-UHFFFAOYSA-N 3-benzyl-5-(5-nitrofuran-2-yl)-1,2,4-oxadiazole Chemical compound O1C([N+](=O)[O-])=CC=C1C1=NC(CC=2C=CC=CC=2)=NO1 ZMUQWPUQGDJPSL-UHFFFAOYSA-N 0.000 claims 1
- QHGSSJBXTNMMMA-UHFFFAOYSA-N 3-cyclopropyl-5-(5-nitrofuran-2-yl)-1,2,4-oxadiazole Chemical compound O1C([N+](=O)[O-])=CC=C1C1=NC(C2CC2)=NO1 QHGSSJBXTNMMMA-UHFFFAOYSA-N 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- PKWFNMPFPRRZTB-UHFFFAOYSA-N 3-phenyl-5-thiophen-3-yl-1,2,4-oxadiazole Chemical compound S1C=CC(C=2ON=C(N=2)C=2C=CC=CC=2)=C1 PKWFNMPFPRRZTB-UHFFFAOYSA-N 0.000 claims 1
- INEUBAZFBRVVBF-UHFFFAOYSA-N 3-pyridin-3-yl-5-(1H-pyrrol-2-yl)-1,2,4-oxadiazole Chemical compound C1=CNC(C=2ON=C(N=2)C=2C=NC=CC=2)=C1 INEUBAZFBRVVBF-UHFFFAOYSA-N 0.000 claims 1
- WEPZABJVPFWWJZ-UHFFFAOYSA-N 5-(1-methylpyrrol-2-yl)-3-pyridin-3-yl-1,2,4-oxadiazole Chemical compound CN1C=CC=C1C1=NC(C=2C=NC=CC=2)=NO1 WEPZABJVPFWWJZ-UHFFFAOYSA-N 0.000 claims 1
- WNMZRKCSRYCUFB-UHFFFAOYSA-N 5-(2-furanyl)-3-(3-pyridinyl)-1,2,4-oxadiazole Chemical compound C1=COC(C=2ON=C(N=2)C=2C=NC=CC=2)=C1 WNMZRKCSRYCUFB-UHFFFAOYSA-N 0.000 claims 1
- OCTTUKXGBNXOGQ-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-pyridin-3-yl-1,2,4-oxadiazole Chemical compound ClC1=CC=CC(C=2ON=C(N=2)C=2C=NC=CC=2)=C1 OCTTUKXGBNXOGQ-UHFFFAOYSA-N 0.000 claims 1
- YYKRPCBJFTUNFZ-UHFFFAOYSA-N 5-(3-nitrophenyl)-3-pyridin-2-yl-1,2,4-oxadiazole Chemical compound [O-][N+](=O)C1=CC=CC(C=2ON=C(N=2)C=2N=CC=CC=2)=C1 YYKRPCBJFTUNFZ-UHFFFAOYSA-N 0.000 claims 1
- RWFYEFJNLLZZGH-UHFFFAOYSA-N 5-(5-nitrofuran-2-yl)-3-phenyl-1,2,4-oxadiazole Chemical compound O1C([N+](=O)[O-])=CC=C1C1=NC(C=2C=CC=CC=2)=NO1 RWFYEFJNLLZZGH-UHFFFAOYSA-N 0.000 claims 1
- NJIFIWADHBPUQL-UHFFFAOYSA-N 5-(5-nitrofuran-2-yl)-3-thiophen-2-yl-1,2,4-oxadiazole Chemical compound O1C([N+](=O)[O-])=CC=C1C1=NC(C=2SC=CC=2)=NO1 NJIFIWADHBPUQL-UHFFFAOYSA-N 0.000 claims 1
- FEDNOYAGHHUWBI-UHFFFAOYSA-N 5-(furan-2-yl)-3-pyridin-4-yl-1,2,4-oxadiazole Chemical compound C1=COC(C=2ON=C(N=2)C=2C=CN=CC=2)=C1 FEDNOYAGHHUWBI-UHFFFAOYSA-N 0.000 claims 1
- 208000030507 AIDS Diseases 0.000 claims 1
- 206010002383 Angina Pectoris Diseases 0.000 claims 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 1
- 206010002660 Anoxia Diseases 0.000 claims 1
- 241000976983 Anoxia Species 0.000 claims 1
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 1
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 1
- 206010003805 Autism Diseases 0.000 claims 1
- 208000020706 Autistic disease Diseases 0.000 claims 1
- 206010008874 Chronic Fatigue Syndrome Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 206010012289 Dementia 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
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- 241000124008 Mammalia Species 0.000 claims 1
- 206010026749 Mania Diseases 0.000 claims 1
- 208000026139 Memory disease Diseases 0.000 claims 1
- 208000019695 Migraine disease Diseases 0.000 claims 1
- 206010028403 Mutism Diseases 0.000 claims 1
- 150000001204 N-oxides Chemical class 0.000 claims 1
- 241000208125 Nicotiana Species 0.000 claims 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims 1
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- 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 claims 1
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- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
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- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 229940005483 opioid analgesics Drugs 0.000 claims 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims 1
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
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- IHNSIFFSNUQGQN-UHFFFAOYSA-N tioxazafen Chemical compound C1=CSC(C=2ON=C(N=2)C=2C=CC=CC=2)=C1 IHNSIFFSNUQGQN-UHFFFAOYSA-N 0.000 claims 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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| EP1845097A1 (en) | 2006-04-10 | 2007-10-17 | Portela & Ca., S.A. | Oxadiazole derivatives as COMT inhibitors |
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| CN101511827B (zh) | 2006-09-07 | 2012-02-01 | 埃科特莱茵药品有限公司 | 作为免疫调制剂的吡啶-4-基衍生物 |
| TWI408139B (zh) | 2006-09-07 | 2013-09-11 | Actelion Pharmaceuticals Ltd | 新穎噻吩衍生物 |
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| JP5645217B2 (ja) * | 2007-12-07 | 2014-12-24 | アッヴィ・ドイチュラント・ゲー・エム・ベー・ハー・ウント・コー・カー・ゲー | ５，６−二置換オキシンドール誘導体およびバソプレッシン依存性疾患を治療するためのこれらの使用 |
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| AU2009217865A1 (en) * | 2008-02-28 | 2009-09-03 | Bial - Portela & Ca., S.A. | Pharmaceutical composition for poorly soluble drugs |
| ES2389469T3 (es) | 2008-03-07 | 2012-10-26 | Actelion Pharmaceuticals Ltd. | Derivados novedosos de aminometilbeceno |
| MX2010009610A (es) | 2008-03-17 | 2010-09-30 | Bial Portela & Ca Sa | Formas de cristal de 5-[3-(2,5-dicloro-4,6-dimetil-1-oxi-piridin-3 -il)-[1,2,4]oxadiazol-5-il]-3-nitrobenceno-1,2-diol. |
| WO2009149135A1 (en) * | 2008-06-04 | 2009-12-10 | Abbott Laboratories | Bis (hetero ) aryl substituted isoxazoles for use as neuronal nicotinic receptor modulators |
| MX2010013399A (es) * | 2008-06-06 | 2010-12-21 | Abbott Lab | Nuevos compuestos de 1,2,4-oxadiazol y sus metodos de uso. |
| MX2011001844A (es) * | 2008-09-02 | 2011-04-05 | Neurosearch As | Derivados de triazol y su uso como moduladores del receptor de acetilcolina nicotinico. |
| US8309584B2 (en) | 2008-09-25 | 2012-11-13 | Green Cross Corporation | Sulfur containing pyrazole-heterocycle derivatives as cannabinoid CB1 receptor antagonists |
| WO2010080757A2 (en) * | 2009-01-07 | 2010-07-15 | Astrazeneca Ab | Combinations with an alpha-4beta-2 nicotinic agonist |
| US8017555B2 (en) | 2009-02-10 | 2011-09-13 | Divergence, Inc. | Compositions and methods for controlling nematodes |
| WO2010106106A1 (en) * | 2009-03-19 | 2010-09-23 | Neurosearch A/S | 2, 5-disubstituted tetrazole derivatives and their use as nicotinic acetylcholine receptor modulators |
| BRPI1014865B1 (pt) | 2009-04-01 | 2020-03-17 | Bial - Portela & C.A., S.A. | Composição que compreende grânulos compreendendo 2,5- dicloro- 3- (5- (3,4- dihidróxi- 5- nitrofenil)- 1,2,4- oxadiazol- 3- il)- 4,6- dimetilpiridina 1- óxido e formulação farmacêutica |
| WO2010138600A2 (en) | 2009-05-29 | 2010-12-02 | Abbott Laboratories | Pharmaceutical compositions for the treatment of pain |
| WO2010151815A2 (en) | 2009-06-25 | 2010-12-29 | Abbott Laboratories | 3,9-diazaspiro[5,5]undecane amides and ureas and methods of use thereof |
| MY153617A (en) | 2009-07-16 | 2015-02-27 | Actelion Pharmaceuticals Ltd | Pyridin-4-yl derivatives |
| AU2011256866B2 (en) | 2010-05-20 | 2014-05-22 | Astrazeneca Ab | New process for the preparation of aryl substituted olefinic amines |
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| DK2665720T3 (en) | 2011-01-19 | 2015-07-13 | Actelion Pharmaceuticals Ltd | 2-methoxy-pyridin-4-yl-yl derivatives |
| US20140045900A1 (en) | 2011-02-11 | 2014-02-13 | Bial-Portela & Ca, S.A. | Administration regime for nitrocatechols |
| RS59666B1 (sr) | 2011-12-13 | 2020-01-31 | BIAL PORTELA & Cª S A | Hemijsko jedinjenje korisno kao intermedijer za pripremu inhibitora katehol-o-metiltransferaze |
| UA118254C2 (uk) | 2012-12-04 | 2018-12-26 | Монсанто Текнолоджи Ллс | Нематоцидні водні композиції концентрату суспензії |
| WO2016083863A1 (en) | 2014-11-28 | 2016-06-02 | Bial - Portela & Ca, S.A. | Medicaments for slowing parkinson's disease |
| SG11201708794PA (en) | 2015-05-20 | 2017-12-28 | Idorsia Pharmaceuticals Ltd | Crystalline form of the compound (s)-3-{4-[5-(2-cyclopentyl-6-methoxy-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-propane-1,2-diol |
| PL3412151T3 (pl) | 2016-02-01 | 2024-05-13 | Sumitomo Chemical Company, Limited | Kompozycja do zwalczania szkodników i sposób zwalczania szkodników |
| US10676467B2 (en) | 2017-06-30 | 2020-06-09 | Washington University | Compositions for binding sphingosine-1-phosphate receptor 1 (S1P1), imaging of S1P1, and methods of use thereof |
| US12089597B2 (en) | 2018-04-13 | 2024-09-17 | Bayer Aktiengesellschaft | Active ingredient combinations with insecticidal, nematicidal and acaricidal properties |
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| US3211742A (en) * | 1962-04-17 | 1965-10-12 | Union Carbide Corp | Process for preparing oxadiazoles |
| IL31990A (en) * | 1968-04-26 | 1974-05-16 | Chinoin Gyogyszer Es Vegyeszet | Pyridyl 1,2,4-oxadiazole derivatives,process for the preparation thereof and pharmaceutical compositions containing same |
| US3574842A (en) * | 1969-11-10 | 1971-04-13 | American Cyanamid Co | Compositions of 4-(1,2,4-oxadiazole-3 or 5-yl)pyridinium salts and method of lowering blood sugar levels with same |
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| DE2709660A1 (de) * | 1977-03-05 | 1978-09-07 | Basf Ag | Sulfonsaeuregruppenhaltige azofarbstoffe mit oxdiazolylresten |
| FR2451932A2 (fr) * | 1979-03-20 | 1980-10-17 | Ugine Kuhlmann | Nouveaux derives du diphenyl-3,5 oxadiazole-1,2,4, leur procede de preparation et leur application a la synthese de matieres colorantes |
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| US5817679A (en) * | 1993-04-01 | 1998-10-06 | University Of Virginia | 7-Azabicyclo 2.2.1!-heptane and -heptene derivatives as cholinergic receptor ligands |
| US6130217A (en) * | 1995-09-20 | 2000-10-10 | Pfizer Inc | Compounds enhancing antitumor activity of other cytotoxic agents |
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| CN1638776A (zh) * | 2001-06-08 | 2005-07-13 | 西托维亚公司 | 取代的3－芳基－5－芳基－[1,2,4]－噁二唑和类似物 |
| FR2832712B1 (fr) * | 2001-11-23 | 2004-02-13 | Sanofi Synthelabo | Derives de 4-(oxadiazol-3-yl)-1,4-diazabicyclo[3.2.2]nonane, leur preparation et leur application en therapeutique |
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| GB0303503D0 (en) | 2003-02-14 | 2003-03-19 | Novartis Ag | Organic compounds |
| US20050075375A1 (en) * | 2003-05-14 | 2005-04-07 | Anadys Pharmaceuticals, Inc. | Heterocyclic compounds for treating hepatitis C virus |
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| JP2007528872A (ja) | 2003-10-01 | 2007-10-18 | メルク エンド カムパニー インコーポレーテッド | Ｓ１ｐ受容体アゴニストとしての３，５−アリール置換、ヘテロアリール置換またはシクロアルキル置換された１，２，４−オキサジアゾール化合物 |
| AU2004299456B2 (en) | 2003-12-17 | 2010-10-07 | Merck Sharp & Dohme Corp. | (3,4-disubstituted)propanoic carboxylates as S1P (Edg) receptor agonists |
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2011
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| US20110294856A1 (en) | 2011-12-01 |
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| US20090312347A1 (en) | 2009-12-17 |
| EP1881979A1 (en) | 2008-01-30 |
| KR20080000622A (ko) | 2008-01-02 |
| IL186360A0 (en) | 2008-01-20 |
| ATE477253T1 (de) | 2010-08-15 |
| WO2006114400A1 (en) | 2006-11-02 |
| MX2007013263A (es) | 2008-01-22 |
| JP2008539195A (ja) | 2008-11-13 |
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