JP2010507619A5 - - Google Patents
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- Publication number
- JP2010507619A5 JP2010507619A5 JP2009533834A JP2009533834A JP2010507619A5 JP 2010507619 A5 JP2010507619 A5 JP 2010507619A5 JP 2009533834 A JP2009533834 A JP 2009533834A JP 2009533834 A JP2009533834 A JP 2009533834A JP 2010507619 A5 JP2010507619 A5 JP 2010507619A5
- Authority
- JP
- Japan
- Prior art keywords
- oxadiazol
- phenyl
- pyridine
- pyridin
- benzonitrile
- 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.)
- Abandoned
Links
- -1 methylenedioxy Chemical group 0.000 claims description 148
- 150000001875 compounds Chemical class 0.000 claims description 76
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 59
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 47
- 150000003839 salts Chemical class 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 125000004076 pyridyl group Chemical group 0.000 claims description 20
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 13
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 12
- 125000002541 furyl group Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000001475 halogen functional group Chemical group 0.000 claims description 11
- 125000001544 thienyl group Chemical group 0.000 claims description 10
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 9
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 9
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 8
- 125000001188 haloalkyl group Chemical group 0.000 claims description 8
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
- 125000000335 thiazolyl group Chemical group 0.000 claims description 8
- 125000005647 linker group Chemical group 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- CGPWBGBIDZEQTL-UHFFFAOYSA-N 2-nitropropanedinitrile Chemical compound [O-][N+](=O)C(C#N)C#N CGPWBGBIDZEQTL-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 4
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 4
- 229940002612 prodrug Drugs 0.000 claims description 4
- 239000000651 prodrug Substances 0.000 claims description 4
- OGVLEPMNNPZAPS-UHFFFAOYSA-N 2,3-difluoropyridine Chemical compound FC1=CC=CN=C1F OGVLEPMNNPZAPS-UHFFFAOYSA-N 0.000 claims description 3
- CMBQUXUTASICGB-UHFFFAOYSA-N 2-(2-fluorophenyl)-5-(1,2-oxazol-5-yl)-1,3,4-oxadiazole Chemical compound FC1=CC=CC=C1C1=NN=C(C=2ON=CC=2)O1 CMBQUXUTASICGB-UHFFFAOYSA-N 0.000 claims description 3
- FMUZLAFJNMYTHG-UHFFFAOYSA-N 2-(3-bromo-4-methylphenyl)-5-(3-fluorophenyl)-1,3,4-oxadiazole Chemical compound C1=C(Br)C(C)=CC=C1C1=NN=C(C=2C=C(F)C=CC=2)O1 FMUZLAFJNMYTHG-UHFFFAOYSA-N 0.000 claims description 3
- ICIAAVLVGRIDNJ-UHFFFAOYSA-N 2-(3-bromo-4-methylphenyl)-5-(4-chlorophenyl)-1,3,4-oxadiazole Chemical compound C1=C(Br)C(C)=CC=C1C1=NN=C(C=2C=CC(Cl)=CC=2)O1 ICIAAVLVGRIDNJ-UHFFFAOYSA-N 0.000 claims description 3
- YFJBOQRYJSWGEH-UHFFFAOYSA-N 2-(3-fluorophenyl)-5-(2-fluoropyridin-3-yl)-1,3,4-oxadiazole Chemical compound FC1=CC=CC(C=2OC(=NN=2)C=2C(=NC=CC=2)F)=C1 YFJBOQRYJSWGEH-UHFFFAOYSA-N 0.000 claims description 3
- QKKPQJPBWLDVJD-UHFFFAOYSA-N 2-(5-bromofuran-2-yl)-5-pyridin-3-yl-1,3,4-oxadiazole Chemical compound O1C(Br)=CC=C1C1=NN=C(C=2C=NC=CC=2)O1 QKKPQJPBWLDVJD-UHFFFAOYSA-N 0.000 claims description 3
- JCXAVCOMFWLXIB-UHFFFAOYSA-N 2-(5-chloro-2,4-dimethoxyphenyl)-5-(5-methyl-1,2-oxazol-3-yl)-1,3,4-oxadiazole Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1C1=NN=C(C2=NOC(C)=C2)O1 JCXAVCOMFWLXIB-UHFFFAOYSA-N 0.000 claims description 3
- QZVPHPKVKZTFPM-UHFFFAOYSA-N 2-[3-(5-pyridin-3-yl-1,3,4-oxadiazol-2-yl)phenyl]acetonitrile Chemical compound N#CCC1=CC=CC(C=2OC(=NN=2)C=2C=NC=CC=2)=C1 QZVPHPKVKZTFPM-UHFFFAOYSA-N 0.000 claims description 3
- XAKQOYXXHZMWNN-UHFFFAOYSA-N 2-[3-[5-(2,5,6-trifluoropyridin-3-yl)-1,3,4-oxadiazol-2-yl]phenyl]acetonitrile Chemical compound N1=C(F)C(F)=CC(C=2OC(=NN=2)C=2C=C(CC#N)C=CC=2)=C1F XAKQOYXXHZMWNN-UHFFFAOYSA-N 0.000 claims description 3
- NPDRAXXZRVVTTH-UHFFFAOYSA-N 2-[3-[5-(6-chloropyridin-3-yl)-1,3,4-oxadiazol-2-yl]phenyl]acetonitrile Chemical compound C1=NC(Cl)=CC=C1C1=NN=C(C=2C=C(CC#N)C=CC=2)O1 NPDRAXXZRVVTTH-UHFFFAOYSA-N 0.000 claims description 3
- QPWKRWCXDWHYKQ-UHFFFAOYSA-N 2-[3-[5-(6-fluoropyridin-3-yl)-1,3,4-oxadiazol-2-yl]phenyl]acetonitrile Chemical compound C1=NC(F)=CC=C1C1=NN=C(C=2C=C(CC#N)C=CC=2)O1 QPWKRWCXDWHYKQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 150000001204 N-oxides Chemical class 0.000 claims description 3
- QEJMFUNQZXAFGU-UHFFFAOYSA-N 2-(furan-2-yl)-5-pyrazin-2-ylsulfanyl-1,3,4-oxadiazole Chemical compound C=1N=CC=NC=1SC(O1)=NN=C1C1=CC=CO1 QEJMFUNQZXAFGU-UHFFFAOYSA-N 0.000 claims description 2
- JRPLIJNANQAYSD-UHFFFAOYSA-N 2-benzylsulfanyl-5-pyridin-3-yl-1,3,4-oxadiazole Chemical compound C=1C=CC=CC=1CSC(O1)=NN=C1C1=CC=CN=C1 JRPLIJNANQAYSD-UHFFFAOYSA-N 0.000 claims description 2
- JWWYYSYRQLPOPE-UHFFFAOYSA-N 3-(5-pyridin-3-yl-1,3,4-thiadiazol-2-yl)benzonitrile Chemical compound N#CC1=CC=CC(C=2SC(=NN=2)C=2C=NC=CC=2)=C1 JWWYYSYRQLPOPE-UHFFFAOYSA-N 0.000 claims description 2
- VXCYUKZOXHXTAZ-UHFFFAOYSA-N 3-[5-(3-cyanophenyl)-1,3,4-thiadiazol-2-yl]benzonitrile Chemical compound N#CC1=CC=CC(C=2SC(=NN=2)C=2C=C(C=CC=2)C#N)=C1 VXCYUKZOXHXTAZ-UHFFFAOYSA-N 0.000 claims description 2
- WSOJVCHQNJGEOS-UHFFFAOYSA-N 4-chloro-2-[5-[2-chloro-5-(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl]phenol Chemical compound OC1=CC=C(Cl)C=C1C1=NN=C(C=2C(=CC=C(C=2)C(F)(F)F)Cl)S1 WSOJVCHQNJGEOS-UHFFFAOYSA-N 0.000 claims description 2
- NSFPLERJOCIKME-UHFFFAOYSA-N 5-(5-pyridin-3-yl-1,3,4-thiadiazol-2-yl)thiophene-2-carbonitrile Chemical compound S1C(C#N)=CC=C1C1=NN=C(C=2C=NC=CC=2)S1 NSFPLERJOCIKME-UHFFFAOYSA-N 0.000 claims description 2
- UIZYWRLCIJJRGB-UHFFFAOYSA-N n-(5-benzylsulfonyl-1,3,4-thiadiazol-2-yl)acetamide Chemical compound S1C(NC(=O)C)=NN=C1S(=O)(=O)CC1=CC=CC=C1 UIZYWRLCIJJRGB-UHFFFAOYSA-N 0.000 claims description 2
- 208000002193 Pain Diseases 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 230000036407 pain Effects 0.000 claims 6
- 208000035475 disorder Diseases 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical group CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- 208000032841 Bulimia Diseases 0.000 claims 2
- 206010006550 Bulimia nervosa Diseases 0.000 claims 2
- 206010010904 Convulsion Diseases 0.000 claims 2
- 206010002026 amyotrophic lateral sclerosis 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
- 201000010099 disease Diseases 0.000 claims 2
- 208000013403 hyperactivity Diseases 0.000 claims 2
- 206010027175 memory impairment 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
- 208000004296 neuralgia Diseases 0.000 claims 2
- 201000001119 neuropathy Diseases 0.000 claims 2
- 230000007823 neuropathy Effects 0.000 claims 2
- 208000033808 peripheral neuropathy Diseases 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 208000024891 symptom Diseases 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims 1
- 208000030507 AIDS Diseases 0.000 claims 1
- 208000002874 Acne Vulgaris Diseases 0.000 claims 1
- 201000004384 Alopecia Diseases 0.000 claims 1
- 206010002383 Angina Pectoris Diseases 0.000 claims 1
- 208000000103 Anorexia Nervosa Diseases 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
- 206010003805 Autism Diseases 0.000 claims 1
- 208000020706 Autistic disease Diseases 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- 108010009685 Cholinergic Receptors Proteins 0.000 claims 1
- 206010008874 Chronic Fatigue Syndrome Diseases 0.000 claims 1
- 208000019888 Circadian rhythm sleep disease 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
- 206010012735 Diarrhoea Diseases 0.000 claims 1
- 201000010374 Down Syndrome Diseases 0.000 claims 1
- 208000012661 Dyskinesia Diseases 0.000 claims 1
- 208000030814 Eating disease Diseases 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 208000026097 Factitious disease Diseases 0.000 claims 1
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 1
- 201000004311 Gilles de la Tourette syndrome 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
- 206010021143 Hypoxia Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 206010065390 Inflammatory pain Diseases 0.000 claims 1
- 208000001456 Jet Lag Syndrome Diseases 0.000 claims 1
- 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
- 241000208125 Nicotiana Species 0.000 claims 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 208000010886 Peripheral nerve injury Diseases 0.000 claims 1
- 208000004983 Phantom Limb Diseases 0.000 claims 1
- 206010056238 Phantom pain Diseases 0.000 claims 1
- 206010034912 Phobia Diseases 0.000 claims 1
- 208000008348 Post-Concussion Syndrome Diseases 0.000 claims 1
- 208000004550 Postoperative Pain Diseases 0.000 claims 1
- 208000005107 Premature Birth Diseases 0.000 claims 1
- 206010036590 Premature baby Diseases 0.000 claims 1
- 206010036618 Premenstrual syndrome Diseases 0.000 claims 1
- 206010052276 Pseudodementia Diseases 0.000 claims 1
- 208000028017 Psychotic disease Diseases 0.000 claims 1
- 206010039966 Senile dementia Diseases 0.000 claims 1
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims 1
- 206010043118 Tardive Dyskinesia Diseases 0.000 claims 1
- 208000000323 Tourette Syndrome Diseases 0.000 claims 1
- 208000016620 Tourette disease Diseases 0.000 claims 1
- 102000034337 acetylcholine receptors Human genes 0.000 claims 1
- 206010000496 acne Diseases 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 230000007953 anoxia Effects 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 230000006793 arrhythmia Effects 0.000 claims 1
- 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
- 230000001684 chronic effect Effects 0.000 claims 1
- 229960003920 cocaine Drugs 0.000 claims 1
- 208000010877 cognitive disease Diseases 0.000 claims 1
- 230000001149 cognitive effect Effects 0.000 claims 1
- 230000009849 deactivation Effects 0.000 claims 1
- 230000006735 deficit Effects 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 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
- 239000003937 drug carrier Substances 0.000 claims 1
- 206010013932 dyslexia Diseases 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 claims 1
- 208000024963 hair loss Diseases 0.000 claims 1
- 230000003676 hair loss Effects 0.000 claims 1
- 201000009863 inflammatory diarrhea Diseases 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 208000033915 jet lag type circadian rhythm sleep disease Diseases 0.000 claims 1
- 230000029849 luteinization Effects 0.000 claims 1
- 240000004308 marijuana Species 0.000 claims 1
- 206010027599 migraine Diseases 0.000 claims 1
- 229960005181 morphine Drugs 0.000 claims 1
- 208000029766 myalgic encephalomeyelitis/chronic fatigue syndrome Diseases 0.000 claims 1
- 201000003631 narcolepsy Diseases 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 208000021722 neuropathic pain Diseases 0.000 claims 1
- 229960002715 nicotine Drugs 0.000 claims 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 208000019906 panic disease Diseases 0.000 claims 1
- 230000002093 peripheral effect Effects 0.000 claims 1
- 208000019899 phobic disease Diseases 0.000 claims 1
- 206010036596 premature ejaculation Diseases 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 230000000306 recurrent effect Effects 0.000 claims 1
- 201000004700 rosacea Diseases 0.000 claims 1
- 230000020341 sensory perception of pain Effects 0.000 claims 1
- 230000001568 sexual effect Effects 0.000 claims 1
- 208000019116 sleep disease Diseases 0.000 claims 1
- 208000020685 sleep-wake disease Diseases 0.000 claims 1
- 230000016160 smooth muscle contraction Effects 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 230000001052 transient effect Effects 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 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 description 3
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 2
- 150000004867 thiadiazoles Chemical class 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 1
- CXGNGMANBKYIEF-UHFFFAOYSA-N n-(5-benzylsulfanyl-1,3,4-thiadiazol-2-yl)acetamide Chemical compound S1C(NC(=O)C)=NN=C1SCC1=CC=CC=C1 CXGNGMANBKYIEF-UHFFFAOYSA-N 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US85407806P | 2006-10-25 | 2006-10-25 | |
| DKPA200601380 | 2006-10-25 | ||
| PCT/EP2007/061433 WO2008049864A1 (en) | 2006-10-25 | 2007-10-24 | Oxadiazole and thiadiazole compounds and their use as nicotinic acetylcholine receptor modulators |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2010507619A JP2010507619A (ja) | 2010-03-11 |
| JP2010507619A5 true JP2010507619A5 (https=) | 2010-08-05 |
Family
ID=38962931
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009533834A Abandoned JP2010507619A (ja) | 2006-10-25 | 2007-10-24 | オキサジアゾール及びチアジアゾール化合物並びにニコチン性アセチルコリン受容体調節物質としてのその使用 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20100029685A1 (https=) |
| EP (1) | EP2079734A1 (https=) |
| JP (1) | JP2010507619A (https=) |
| AU (1) | AU2007310897A1 (https=) |
| CA (1) | CA2667545A1 (https=) |
| IL (1) | IL197397A0 (https=) |
| MX (1) | MX2009003892A (https=) |
| NO (1) | NO20091977L (https=) |
| WO (1) | WO2008049864A1 (https=) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2013203849B2 (en) * | 2007-08-13 | 2016-01-14 | Monsanto Technology Llc | Compositions and methods for controlling nematodes |
| AU2008286879B2 (en) | 2007-08-13 | 2013-08-22 | Monsanto Technology Llc | Compositions and methods for controlling nematodes |
| GB0723719D0 (en) * | 2007-12-04 | 2008-01-16 | Glaxo Group Ltd | Compounds |
| GB0723815D0 (en) * | 2007-12-05 | 2008-01-16 | Glaxo Group Ltd | Compounds |
| WO2009149135A1 (en) * | 2008-06-04 | 2009-12-10 | Abbott Laboratories | Bis (hetero ) aryl substituted isoxazoles for use as neuronal nicotinic receptor modulators |
| EP2583556B1 (de) * | 2008-07-17 | 2016-01-20 | Bayer CropScience AG | Heterocyclische Verbindungen als Schädlingsbekämpfungsmittel |
| CA2735773A1 (en) * | 2008-09-02 | 2010-03-11 | Neurosearch A/S | Triazole derivatives and their use as nicotinic acetylcholine receptor modulators |
| CN105418598B (zh) | 2009-02-10 | 2019-05-17 | 孟山都技术有限公司 | 用于控制线虫的组合物和方法 |
| US9095596B2 (en) * | 2009-10-15 | 2015-08-04 | Southern Research Institute | Treatment of neurodegenerative diseases, causation of memory enhancement, and assay for screening compounds for such |
| WO2011073299A1 (en) | 2009-12-18 | 2011-06-23 | Neurosearch A/S | Pyridinyl oxadiazole compounds and their use as nicotinic acetylcholine receptor modulators |
| EP2568809A4 (en) | 2010-05-12 | 2013-11-06 | Univ Vanderbilt | HETEROCYCLIC ALLOSTERE SULFON MGLUR4 POTENTIATORS, COMPOSITIONS AND METHODS OF TREATING NEUROLOGICAL DYSFUNCTIONS |
| JP5826848B2 (ja) | 2010-09-02 | 2015-12-02 | モンサント テクノロジー エルエルシー | 線虫を防除する新規組成物および方法 |
| BR112013009823A2 (pt) * | 2010-10-22 | 2016-07-05 | Bayer Ip Gmbh | novos compostos heterocíclicos como pesticidas |
| US9173401B2 (en) | 2013-03-15 | 2015-11-03 | Monsanto Technology Llc | N-,C-disubstituted azoles and compositions and methods for controlling nematode pests |
| CZ305680B6 (cs) * | 2013-04-04 | 2016-02-03 | Univerzita Karlova v Praze, Farmaceutická fakulta v Hradci Králové | Substituovaný diazol, jeho použití a farmaceutický přípravek ho obsahující |
| US10513110B2 (en) * | 2014-06-13 | 2019-12-24 | Electronics For Imaging, Inc. | Integration of a line-scan camera on a single pass inkjet printer |
| IL294124B2 (en) | 2015-12-10 | 2024-02-01 | Ptc Therapeutics Inc | Methods for treating huntington's disease |
| US11407753B2 (en) | 2017-06-05 | 2022-08-09 | Ptc Therapeutics, Inc. | Compounds for treating Huntington's disease |
| WO2019005993A1 (en) | 2017-06-28 | 2019-01-03 | Ptc Therapeutics, Inc. | METHODS OF TREATING HUNTINGTON'S DISEASE |
| US11382918B2 (en) | 2017-06-28 | 2022-07-12 | Ptc Therapeutics, Inc. | Methods for treating Huntington's Disease |
| MX2020009957A (es) | 2018-03-27 | 2021-01-15 | Ptc Therapeutics Inc | Compuestos para el tratamiento de enfermedad de hungtinton. |
| PL3814357T3 (pl) | 2018-06-27 | 2024-09-16 | Ptc Therapeutics, Inc. | Związki heterocykliczne i heteroarylowe do leczenia choroby huntingtona |
| EP3814345B8 (en) | 2018-06-27 | 2024-10-30 | PTC Therapeutics, Inc. | Heteroaryl compounds for treating huntington's disease |
| EP3814360B8 (en) | 2018-06-27 | 2024-11-06 | PTC Therapeutics, Inc. | Heteroaryl compounds for treating huntington's disease |
| WO2020231977A1 (en) | 2019-05-13 | 2020-11-19 | Ptc Therapeutics, Inc. | Compounds for treating huntington's disease |
| AU2020341464A1 (en) * | 2019-09-05 | 2022-04-21 | Trevena, Inc. | Methods of treating epilepsy using the same |
Family Cites Families (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH411906A (de) * | 1960-03-01 | 1966-04-30 | Ciba Geigy | Verfahren zur Herstellung neuer 1,3,4-Thiadiazole |
| NL261797A (https=) * | 1960-03-01 | |||
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| US6699853B2 (en) * | 1997-06-16 | 2004-03-02 | Hoechst Schering Agrevo Gmbh | 4-haloalkyl-3-heterocyclylpyridines, 4-haloalkyl-5-heterocyclyl-pyrimidines and 4-trifluoromethyl-3-oxadiazolylpyridines, processes for their preparation, compositions comprising them, and their use as pesticides |
| DE19725450A1 (de) * | 1997-06-16 | 1998-12-17 | Hoechst Schering Agrevo Gmbh | 4-Haloalkyl-3-heterocyclylpyridine und 4-Haloalkyl-5-heterocyclylpyrimidine, Verfahren zu ihrer Herstellung, sie enthaltende Mittel und ihre Verwendung als Schädlingsbekämpfungsmittel |
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| EP2044926B1 (en) * | 2006-07-20 | 2018-01-10 | National University Corporation Okayama University | Oral composition for dental purposes |
| PT2195311E (pt) * | 2007-08-17 | 2011-05-25 | Actelion Pharmaceuticals Ltd | Derivados de piridina como moduladores do receptor s1p1/edg1 |
| CA2695434A1 (en) * | 2007-08-17 | 2009-02-26 | Astrazeneca Ab | Chemical compounds 979 |
| EP2240474B1 (en) * | 2007-12-26 | 2012-03-14 | Sanofi | Cyclic pyridyl-n-(1,3,4)-thiadiazol-2-yl-benzene sulfonamides, processes for their preparation and their use as pharmaceuticals |
| MX2010013264A (es) * | 2008-06-09 | 2011-02-25 | Sanofi Aventis | Sulfonamidas n-heterociclicas aneladas con grupo de cabeza de oxadiazolona, procesos para su preparacion y su uso como sustancias farmaceuticas. |
| US20100249071A1 (en) * | 2009-03-30 | 2010-09-30 | Exelixis, Inc. | Modulators of S1P and Methods of Making And Using |
| SA110310332B1 (ar) * | 2009-05-01 | 2013-12-10 | Astrazeneca Ab | مركبات ميثانون (3 استبدال -ازيتيدين -1-يل )(5- فينيل -1، 3، 4- أوكساديازول -2-يل ) |
| US8399451B2 (en) * | 2009-08-07 | 2013-03-19 | Bristol-Myers Squibb Company | Heterocyclic compounds |
-
2007
- 2007-10-24 WO PCT/EP2007/061433 patent/WO2008049864A1/en not_active Ceased
- 2007-10-24 MX MX2009003892A patent/MX2009003892A/es not_active Application Discontinuation
- 2007-10-24 AU AU2007310897A patent/AU2007310897A1/en not_active Abandoned
- 2007-10-24 EP EP07821796A patent/EP2079734A1/en not_active Withdrawn
- 2007-10-24 US US12/447,205 patent/US20100029685A1/en not_active Abandoned
- 2007-10-24 JP JP2009533834A patent/JP2010507619A/ja not_active Abandoned
- 2007-10-24 CA CA002667545A patent/CA2667545A1/en not_active Abandoned
-
2009
- 2009-03-04 IL IL197397A patent/IL197397A0/en unknown
- 2009-05-20 NO NO20091977A patent/NO20091977L/no not_active Application Discontinuation
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