CA2606087A1 - Novel oxadiazole derivatives and their medical use - Google Patents
Novel oxadiazole derivatives and their medical use Download PDFInfo
- Publication number
- CA2606087A1 CA2606087A1 CA002606087A CA2606087A CA2606087A1 CA 2606087 A1 CA2606087 A1 CA 2606087A1 CA 002606087 A CA002606087 A CA 002606087A CA 2606087 A CA2606087 A CA 2606087A CA 2606087 A1 CA2606087 A1 CA 2606087A1
- Authority
- CA
- Canada
- Prior art keywords
- nitro
- oxadiazol
- phenyl
- pyridine
- cycloalkyl
- 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
- 150000004866 oxadiazoles Chemical class 0.000 title claims abstract description 45
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 76
- 201000010099 disease Diseases 0.000 claims abstract description 40
- 208000035475 disorder Diseases 0.000 claims abstract description 36
- 238000011282 treatment Methods 0.000 claims abstract description 34
- 208000002193 Pain Diseases 0.000 claims abstract description 32
- 239000000126 substance Substances 0.000 claims abstract description 10
- 230000004770 neurodegeneration Effects 0.000 claims abstract description 8
- 230000016160 smooth muscle contraction Effects 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 52
- 125000005843 halogen group Chemical group 0.000 claims description 48
- 125000001188 haloalkyl group Chemical group 0.000 claims description 47
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 47
- 125000003118 aryl group Chemical group 0.000 claims description 45
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 45
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 42
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 40
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 39
- 125000003545 alkoxy group Chemical group 0.000 claims description 37
- 125000002541 furyl group Chemical group 0.000 claims description 37
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 33
- 125000001544 thienyl group Chemical group 0.000 claims description 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
- 125000001424 substituent group Chemical group 0.000 claims description 30
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 29
- 125000004076 pyridyl group Chemical group 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 25
- 125000000623 heterocyclic group Chemical group 0.000 claims description 22
- 125000001620 monocyclic carbocycle group Chemical group 0.000 claims description 20
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 20
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 20
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- 125000001153 fluoro group Chemical group F* 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 15
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 15
- 230000002265 prevention Effects 0.000 claims description 13
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 229960002715 nicotine Drugs 0.000 claims description 12
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims description 12
- 125000000335 thiazolyl group Chemical group 0.000 claims description 11
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims description 10
- 230000006735 deficit Effects 0.000 claims description 10
- 201000000980 schizophrenia Diseases 0.000 claims description 10
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims description 9
- 208000004296 neuralgia Diseases 0.000 claims description 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 206010010904 Convulsion Diseases 0.000 claims description 8
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims description 8
- 206010012735 Diarrhoea Diseases 0.000 claims description 8
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
- 230000001225 therapeutic effect Effects 0.000 claims description 8
- 206010020651 Hyperkinesia Diseases 0.000 claims description 7
- 208000000269 Hyperkinesis Diseases 0.000 claims description 7
- 206010043118 Tardive Dyskinesia Diseases 0.000 claims description 7
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 7
- 208000024827 Alzheimer disease Diseases 0.000 claims description 6
- 208000032841 Bulimia Diseases 0.000 claims description 6
- 206010006550 Bulimia nervosa Diseases 0.000 claims description 6
- 108010009685 Cholinergic Receptors Proteins 0.000 claims description 6
- 208000026097 Factitious disease Diseases 0.000 claims description 6
- 241001465754 Metazoa Species 0.000 claims description 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 description 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 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 description 6
- 208000019901 Anxiety disease Diseases 0.000 claims description 5
- 208000020925 Bipolar disease Diseases 0.000 claims description 5
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 206010015037 epilepsy Diseases 0.000 claims description 5
- 208000027866 inflammatory disease Diseases 0.000 claims description 5
- 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 description 5
- 208000021722 neuropathic pain Diseases 0.000 claims description 5
- PMUYBTQNMMMWIU-UHFFFAOYSA-N 5-(3-nitrophenyl)-3-pyridin-3-yl-1,2,4-oxadiazole Chemical compound [O-][N+](=O)C1=CC=CC(C=2ON=C(N=2)C=2C=NC=CC=2)=C1 PMUYBTQNMMMWIU-UHFFFAOYSA-N 0.000 claims description 4
- 208000002874 Acne Vulgaris Diseases 0.000 claims description 4
- 206010002383 Angina Pectoris Diseases 0.000 claims description 4
- 206010002660 Anoxia Diseases 0.000 claims description 4
- 241000976983 Anoxia Species 0.000 claims description 4
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 4
- 206010012289 Dementia Diseases 0.000 claims description 4
- 206010019233 Headaches Diseases 0.000 claims description 4
- 206010021143 Hypoxia Diseases 0.000 claims description 4
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 4
- 208000019695 Migraine disease Diseases 0.000 claims description 4
- 208000008589 Obesity Diseases 0.000 claims description 4
- 208000010886 Peripheral nerve injury Diseases 0.000 claims description 4
- 208000004983 Phantom Limb Diseases 0.000 claims description 4
- 206010056238 Phantom pain Diseases 0.000 claims description 4
- 208000004550 Postoperative Pain Diseases 0.000 claims description 4
- 206010036600 Premature labour Diseases 0.000 claims description 4
- 208000028017 Psychotic disease Diseases 0.000 claims description 4
- 206010000496 acne Diseases 0.000 claims description 4
- 230000001154 acute effect Effects 0.000 claims description 4
- 230000007953 anoxia Effects 0.000 claims description 4
- 208000006673 asthma Diseases 0.000 claims description 4
- 230000001684 chronic effect Effects 0.000 claims description 4
- 208000010877 cognitive disease Diseases 0.000 claims description 4
- 230000001149 cognitive effect Effects 0.000 claims description 4
- 230000036461 convulsion Effects 0.000 claims description 4
- 230000004064 dysfunction Effects 0.000 claims description 4
- 230000001856 erectile effect Effects 0.000 claims description 4
- 230000002757 inflammatory effect Effects 0.000 claims description 4
- 206010027599 migraine Diseases 0.000 claims description 4
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 4
- 235000020824 obesity Nutrition 0.000 claims description 4
- 206010036596 premature ejaculation Diseases 0.000 claims description 4
- 229940002612 prodrug Drugs 0.000 claims description 4
- 239000000651 prodrug Substances 0.000 claims description 4
- 230000000306 recurrent effect Effects 0.000 claims description 4
- 201000004700 rosacea Diseases 0.000 claims description 4
- 208000017520 skin disease Diseases 0.000 claims description 4
- 230000001052 transient effect Effects 0.000 claims description 4
- AFVRVPHPSWAWFD-UHFFFAOYSA-N 3-(3-nitrophenyl)-5-pyridin-3-yl-1,2,4-oxadiazole Chemical compound [O-][N+](=O)C1=CC=CC(C=2N=C(ON=2)C=2C=NC=CC=2)=C1 AFVRVPHPSWAWFD-UHFFFAOYSA-N 0.000 claims description 3
- HGFXDSQLRSWUBO-UHFFFAOYSA-N 3-(3-pyridin-3-yl-1,2,4-oxadiazol-5-yl)benzonitrile Chemical compound N#CC1=CC=CC(C=2ON=C(N=2)C=2C=NC=CC=2)=C1 HGFXDSQLRSWUBO-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- STVWNXNEBUAGLY-UHFFFAOYSA-N 3-pyridin-3-yl-5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazole Chemical compound FC(F)(F)C1=CC=CC(C=2ON=C(N=2)C=2C=NC=CC=2)=C1 STVWNXNEBUAGLY-UHFFFAOYSA-N 0.000 claims description 3
- RSWOEPMGEMCOKR-UHFFFAOYSA-N 5-(1H-pyrazol-4-yl)-3-pyridin-3-yl-1,2,4-oxadiazole Chemical compound C1=NNC=C1C1=NC(C=2C=NC=CC=2)=NO1 RSWOEPMGEMCOKR-UHFFFAOYSA-N 0.000 claims description 3
- RDYLSOPUOHCJJU-UHFFFAOYSA-N 5-(2-methyl-1,3-thiazol-4-yl)-3-pyridin-3-yl-1,2,4-oxadiazole Chemical compound S1C(C)=NC(C=2ON=C(N=2)C=2C=NC=CC=2)=C1 RDYLSOPUOHCJJU-UHFFFAOYSA-N 0.000 claims description 3
- XOSBTRLEIPRXJN-UHFFFAOYSA-N 5-(2-nitrophenyl)-3-pyridin-3-yl-1,2,4-oxadiazole Chemical compound [O-][N+](=O)C1=CC=CC=C1C1=NC(C=2C=NC=CC=2)=NO1 XOSBTRLEIPRXJN-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- SQVWLKBGCYVLLN-UHFFFAOYSA-N 5-(3-fluorophenyl)-3-pyridin-3-yl-1,2,4-oxadiazole Chemical compound FC1=CC=CC(C=2ON=C(N=2)C=2C=NC=CC=2)=C1 SQVWLKBGCYVLLN-UHFFFAOYSA-N 0.000 claims description 3
- BZHIVZTUKJVHBB-UHFFFAOYSA-N 5-(3-nitrophenyl)-3-pyrazin-2-yl-1,2,4-oxadiazole Chemical compound [O-][N+](=O)C1=CC=CC(C=2ON=C(N=2)C=2N=CC=NC=2)=C1 BZHIVZTUKJVHBB-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- IMSXHNJZMPDAEB-UHFFFAOYSA-N 5-(3-nitrophenyl)-3-pyridin-4-yl-1,2,4-oxadiazole Chemical compound [O-][N+](=O)C1=CC=CC(C=2ON=C(N=2)C=2C=CN=CC=2)=C1 IMSXHNJZMPDAEB-UHFFFAOYSA-N 0.000 claims description 3
- YKKMKYMLNAUMFB-UHFFFAOYSA-N 5-(4-nitrophenyl)-3-pyridin-3-yl-1,2,4-oxadiazole Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=NC(C=2C=NC=CC=2)=NO1 YKKMKYMLNAUMFB-UHFFFAOYSA-N 0.000 claims description 3
- HWXLMHMENDXALF-UHFFFAOYSA-N 5-(5-nitrofuran-2-yl)-3-pyrazin-2-yl-1,2,4-oxadiazole Chemical compound O1C([N+](=O)[O-])=CC=C1C1=NC(C=2N=CC=NC=2)=NO1 HWXLMHMENDXALF-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- UAQDTDBRGYGJFK-UHFFFAOYSA-N 5-(furan-3-yl)-3-pyridin-3-yl-1,2,4-oxadiazole Chemical compound O1C=CC(C=2ON=C(N=2)C=2C=NC=CC=2)=C1 UAQDTDBRGYGJFK-UHFFFAOYSA-N 0.000 claims description 3
- MUWKXFLEESJMCT-UHFFFAOYSA-N 5-phenyl-3-pyridin-3-yl-1,2,4-oxadiazole Chemical compound C1=CC=CC=C1C1=NC(C=2C=NC=CC=2)=NO1 MUWKXFLEESJMCT-UHFFFAOYSA-N 0.000 claims description 3
- 208000030507 AIDS Diseases 0.000 claims description 3
- 208000000103 Anorexia Nervosa Diseases 0.000 claims description 3
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 3
- 206010003805 Autism Diseases 0.000 claims description 3
- 208000020706 Autistic disease Diseases 0.000 claims description 3
- 206010008874 Chronic Fatigue Syndrome Diseases 0.000 claims description 3
- 208000019888 Circadian rhythm sleep disease Diseases 0.000 claims description 3
- 208000030814 Eating disease Diseases 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 3
- 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 description 3
- 208000023105 Huntington disease Diseases 0.000 claims description 3
- 206010020772 Hypertension Diseases 0.000 claims description 3
- 206010065390 Inflammatory pain Diseases 0.000 claims description 3
- 208000001456 Jet Lag Syndrome Diseases 0.000 claims description 3
- 206010026749 Mania Diseases 0.000 claims description 3
- 208000026139 Memory disease Diseases 0.000 claims description 3
- 206010028403 Mutism Diseases 0.000 claims description 3
- 150000001204 N-oxides Chemical class 0.000 claims description 3
- 241000208125 Nicotiana Species 0.000 claims description 3
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims description 3
- 208000018737 Parkinson disease Diseases 0.000 claims description 3
- 208000008348 Post-Concussion Syndrome Diseases 0.000 claims description 3
- 206010036618 Premenstrual syndrome Diseases 0.000 claims description 3
- 206010052276 Pseudodementia Diseases 0.000 claims description 3
- 206010039966 Senile dementia Diseases 0.000 claims description 3
- 206010041250 Social phobia Diseases 0.000 claims description 3
- 208000000323 Tourette Syndrome Diseases 0.000 claims description 3
- 208000016620 Tourette disease Diseases 0.000 claims description 3
- 230000036506 anxiety Effects 0.000 claims description 3
- 206010003119 arrhythmia Diseases 0.000 claims description 3
- 230000006793 arrhythmia Effects 0.000 claims description 3
- 229940049706 benzodiazepine Drugs 0.000 claims description 3
- 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 claims description 3
- 208000028683 bipolar I disease Diseases 0.000 claims description 3
- 229960003920 cocaine Drugs 0.000 claims description 3
- 229960002069 diamorphine Drugs 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 235000014632 disordered eating Nutrition 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 206010013932 dyslexia Diseases 0.000 claims description 3
- 208000033915 jet lag type circadian rhythm sleep disease Diseases 0.000 claims description 3
- 230000029849 luteinization Effects 0.000 claims description 3
- 229960005181 morphine Drugs 0.000 claims description 3
- 208000029766 myalgic encephalomeyelitis/chronic fatigue syndrome Diseases 0.000 claims description 3
- 201000003631 narcolepsy Diseases 0.000 claims description 3
- 201000001119 neuropathy Diseases 0.000 claims description 3
- 230000007823 neuropathy Effects 0.000 claims description 3
- 229940005483 opioid analgesics Drugs 0.000 claims description 3
- 208000019906 panic disease Diseases 0.000 claims description 3
- 208000033808 peripheral neuropathy Diseases 0.000 claims description 3
- 230000020341 sensory perception of pain Effects 0.000 claims description 3
- 208000011580 syndromic disease Diseases 0.000 claims description 3
- 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 description 3
- 208000002271 trichotillomania Diseases 0.000 claims description 3
- NLDUIBYQNUWQSZ-UHFFFAOYSA-N 3-(3-pyridin-3-yl-1,2,4-oxadiazol-5-yl)aniline Chemical compound NC1=CC=CC(C=2ON=C(N=2)C=2C=NC=CC=2)=C1 NLDUIBYQNUWQSZ-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- FJPQAGJOPJCKMP-UHFFFAOYSA-N 5-(3-pyridin-3-yl-1,2,4-oxadiazol-5-yl)furan-2-carbonitrile Chemical compound O1C(C#N)=CC=C1C1=NC(C=2C=NC=CC=2)=NO1 FJPQAGJOPJCKMP-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- ZFFODQCAAWHVDQ-UHFFFAOYSA-N 5-(5-nitrofuran-3-yl)-3-pyridin-2-yl-1,2,4-oxadiazole Chemical compound O1C([N+](=O)[O-])=CC(C=2ON=C(N=2)C=2N=CC=CC=2)=C1 ZFFODQCAAWHVDQ-UHFFFAOYSA-N 0.000 claims description 2
- HHLUNKPCYGOYAZ-UHFFFAOYSA-N 5-(5-nitrofuran-3-yl)-3-pyridin-3-yl-1,2,4-oxadiazole Chemical compound O1C([N+](=O)[O-])=CC(C=2ON=C(N=2)C=2C=NC=CC=2)=C1 HHLUNKPCYGOYAZ-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- WXCZEZVPNSMKOZ-UHFFFAOYSA-N 6-(3-pyridin-3-yl-1,2,4-oxadiazol-5-yl)pyridine-2-carbonitrile Chemical compound N#CC1=CC=CC(C=2ON=C(N=2)C=2C=NC=CC=2)=N1 WXCZEZVPNSMKOZ-UHFFFAOYSA-N 0.000 claims description 2
- 241000124008 Mammalia Species 0.000 claims description 2
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 2
- 102000034337 acetylcholine receptors Human genes 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 abstract description 85
- 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 abstract description 17
- 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 abstract description 17
- 210000003169 central nervous system Anatomy 0.000 abstract description 10
- 230000001713 cholinergic effect Effects 0.000 abstract description 6
- 208000017701 Endocrine disease Diseases 0.000 abstract description 5
- 230000000144 pharmacologic effect Effects 0.000 abstract description 5
- 206010061218 Inflammation Diseases 0.000 abstract description 4
- 208000030172 endocrine system disease Diseases 0.000 abstract description 4
- 230000004054 inflammatory process Effects 0.000 abstract description 4
- 210000000653 nervous system Anatomy 0.000 abstract description 2
- 208000024891 symptom Diseases 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 239000000543 intermediate Substances 0.000 description 11
- 102000005962 receptors Human genes 0.000 description 9
- 108020003175 receptors Proteins 0.000 description 9
- 230000004044 response Effects 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 230000003287 optical effect Effects 0.000 description 7
- 210000001428 peripheral nervous system Anatomy 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000007796 conventional method Methods 0.000 description 5
- 102000009660 Cholinergic Receptors Human genes 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- VTXHIFQMAGRQSN-UHFFFAOYSA-N 5-(5-nitrofuran-2-yl)-3-pyridin-3-yl-1,2,4-oxadiazole Chemical compound O1C([N+](=O)[O-])=CC=C1C1=NC(C=2C=NC=CC=2)=NO1 VTXHIFQMAGRQSN-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- -1 cyclopropylethyl Chemical group 0.000 description 3
- AQBMQGDKWIPBRF-UHFFFAOYSA-N n'-hydroxypyridine-3-carboximidamide Chemical compound ON=C(N)C1=CC=CN=C1 AQBMQGDKWIPBRF-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000002560 therapeutic procedure Methods 0.000 description 3
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 2
- NWLUQYBFZRZQKF-UHFFFAOYSA-N 5-(6-bromopyridin-2-yl)-3-pyridin-3-yl-1,2,4-oxadiazole Chemical compound BrC1=CC=CC(C=2ON=C(N=2)C=2C=NC=CC=2)=N1 NWLUQYBFZRZQKF-UHFFFAOYSA-N 0.000 description 2
- OLEFNFXYGGTROA-UHFFFAOYSA-N 5-nitrofuran-2-carbonyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)O1 OLEFNFXYGGTROA-UHFFFAOYSA-N 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 description 2
- 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 206010057852 Nicotine dependence Diseases 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 208000025569 Tobacco Use disease Diseases 0.000 description 2
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 2
- 229960004373 acetylcholine Drugs 0.000 description 2
- 230000003281 allosteric effect Effects 0.000 description 2
- MXOQNVMDKHLYCZ-UHFFFAOYSA-N benzamidoxime Chemical compound ON=C(N)C1=CC=CC=C1 MXOQNVMDKHLYCZ-UHFFFAOYSA-N 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 238000002405 diagnostic procedure Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 238000003384 imaging method Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000012544 monitoring process Methods 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 238000002610 neuroimaging Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000000069 prophylactic effect Effects 0.000 description 2
- WRHZVMBBRYBTKZ-UHFFFAOYSA-N pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC=CN1 WRHZVMBBRYBTKZ-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- QIQITDHWZYEEPA-UHFFFAOYSA-N thiophene-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CS1 QIQITDHWZYEEPA-UHFFFAOYSA-N 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 1
- WSWCOQWTEOXDQX-MQQKCMAXSA-M (E,E)-sorbate Chemical compound C\C=C\C=C\C([O-])=O WSWCOQWTEOXDQX-MQQKCMAXSA-M 0.000 description 1
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- KWLGFSHSTADSKH-UHFFFAOYSA-N 1h-pyrazole-4-carbonyl chloride Chemical compound ClC(=O)C=1C=NNC=1 KWLGFSHSTADSKH-UHFFFAOYSA-N 0.000 description 1
- SFGNNBCWQOIVAZ-UHFFFAOYSA-N 1h-pyrrole-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CN1 SFGNNBCWQOIVAZ-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- KHORPZFSYQUYDV-UHFFFAOYSA-N 2-methyl-1,3-thiazole-4-carbonyl chloride Chemical compound CC1=NC(C(Cl)=O)=CS1 KHORPZFSYQUYDV-UHFFFAOYSA-N 0.000 description 1
- BWWHTIHDQBHTHP-UHFFFAOYSA-N 2-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC=C1C(Cl)=O BWWHTIHDQBHTHP-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- CXAMGIFFLJLHLV-UHFFFAOYSA-N 3-(4-fluorophenyl)-5-(5-nitrofuran-2-yl)-1,2,4-oxadiazole Chemical compound O1C([N+](=O)[O-])=CC=C1C1=NC(C=2C=CC(F)=CC=2)=NO1 CXAMGIFFLJLHLV-UHFFFAOYSA-N 0.000 description 1
- WHIHIKVIWVIIER-UHFFFAOYSA-N 3-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC(Cl)=C1 WHIHIKVIWVIIER-UHFFFAOYSA-N 0.000 description 1
- RPESZQVUWMFBEO-UHFFFAOYSA-N 3-cyanobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC(C#N)=C1 RPESZQVUWMFBEO-UHFFFAOYSA-N 0.000 description 1
- SYVNVEGIRVXRQH-UHFFFAOYSA-N 3-fluorobenzoyl chloride Chemical compound FC1=CC=CC(C(Cl)=O)=C1 SYVNVEGIRVXRQH-UHFFFAOYSA-N 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- NXTNASSYJUXJDV-UHFFFAOYSA-N 3-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC(C(Cl)=O)=C1 NXTNASSYJUXJDV-UHFFFAOYSA-N 0.000 description 1
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- OSUPWUQRPLIJKX-UHFFFAOYSA-N 4-fluoro-n'-hydroxybenzenecarboximidamide Chemical compound ON=C(N)C1=CC=C(F)C=C1 OSUPWUQRPLIJKX-UHFFFAOYSA-N 0.000 description 1
- SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- KZQSLSZKPQSRGF-UHFFFAOYSA-N 5-(5-bromofuran-2-yl)-3-pyridin-3-yl-1,2,4-oxadiazole Chemical compound O1C(Br)=CC=C1C1=NC(C=2C=NC=CC=2)=NO1 KZQSLSZKPQSRGF-UHFFFAOYSA-N 0.000 description 1
- IVLVFEYMTXAQNT-UHFFFAOYSA-N 5-(5-bromothiophen-2-yl)-3-pyridin-3-yl-1,2,4-oxadiazole Chemical compound S1C(Br)=CC=C1C1=NC(C=2C=NC=CC=2)=NO1 IVLVFEYMTXAQNT-UHFFFAOYSA-N 0.000 description 1
- UXWUEQZKZUCHRV-UHFFFAOYSA-N 5-(5-nitrofuran-2-yl)-3-pyridin-2-yl-1,2,4-oxadiazole Chemical compound O1C([N+](=O)[O-])=CC=C1C1=NC(C=2N=CC=CC=2)=NO1 UXWUEQZKZUCHRV-UHFFFAOYSA-N 0.000 description 1
- VABZRAFKJLBBMK-UHFFFAOYSA-N 5-(5-nitrofuran-2-yl)-3-pyridin-4-yl-1,2,4-oxadiazole Chemical compound O1C([N+](=O)[O-])=CC=C1C1=NC(C=2C=CN=CC=2)=NO1 VABZRAFKJLBBMK-UHFFFAOYSA-N 0.000 description 1
- QLVNUZPODFIOGC-UHFFFAOYSA-N 5-bromofuran-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=C(Br)O1 QLVNUZPODFIOGC-UHFFFAOYSA-N 0.000 description 1
- ORIONTBOMZNQIE-UHFFFAOYSA-N 5-bromothiophene-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=C(Br)S1 ORIONTBOMZNQIE-UHFFFAOYSA-N 0.000 description 1
- UBJUDOWYGUICSE-UHFFFAOYSA-N 6-bromopyridine-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CC(Br)=N1 UBJUDOWYGUICSE-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 208000020401 Depressive disease Diseases 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 1
- 101000938351 Homo sapiens Ephrin type-A receptor 3 Proteins 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 206010020850 Hyperthyroidism Diseases 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 102000004086 Ligand-Gated Ion Channels Human genes 0.000 description 1
- 108090000543 Ligand-Gated Ion Channels Proteins 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
- 108010052285 Membrane Proteins Proteins 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- 229910017912 NH2OH Inorganic materials 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- GCTFWCDSFPMHHS-UHFFFAOYSA-M Tributyltin chloride Chemical compound CCCC[Sn](Cl)(CCCC)CCCC GCTFWCDSFPMHHS-UHFFFAOYSA-M 0.000 description 1
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 229940072107 ascorbate Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000003828 azulenyl group Chemical group 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 210000005013 brain tissue Anatomy 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical class C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 208000015114 central nervous system disease Diseases 0.000 description 1
- ZUUATXHRJFHSGO-UHFFFAOYSA-N chembl1896408 Chemical compound O/N=C(/N)C1=CC=NC=C1 ZUUATXHRJFHSGO-UHFFFAOYSA-N 0.000 description 1
- XKXCGXSHUNVFCT-UHFFFAOYSA-N chembl3263490 Chemical compound ON=C(N)C1=CC=CC=N1 XKXCGXSHUNVFCT-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229940114081 cinnamate Drugs 0.000 description 1
- 230000019771 cognition Effects 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 125000004966 cyanoalkyl group Chemical group 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000000000 cycloalkoxy group Chemical group 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000000032 diagnostic agent Substances 0.000 description 1
- 229940039227 diagnostic agent Drugs 0.000 description 1
- WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229950005627 embonate Drugs 0.000 description 1
- 229950011470 enantate Drugs 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 210000002816 gill Anatomy 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 102000057382 human EPHA3 Human genes 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000004807 localization Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- OMCUPXRCMTUDHI-UHFFFAOYSA-N n'-hydroxycyclopropanecarboximidamide Chemical compound ON=C(N)C1CC1 OMCUPXRCMTUDHI-UHFFFAOYSA-N 0.000 description 1
- NKMNPRXPUZINOM-UHFFFAOYSA-N n'-hydroxythiophene-2-carboximidamide Chemical compound ON=C(N)C1=CC=CS1 NKMNPRXPUZINOM-UHFFFAOYSA-N 0.000 description 1
- QTEPOLHNAWPMRG-UHFFFAOYSA-N n-[3-(3-pyridin-3-yl-1,2,4-oxadiazol-5-yl)phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(C=2ON=C(N=2)C=2C=NC=CC=2)=C1 QTEPOLHNAWPMRG-UHFFFAOYSA-N 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 208000028591 pheochromocytoma Diseases 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229940126027 positive allosteric modulator Drugs 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- DOYOPBSXEIZLRE-UHFFFAOYSA-N pyrrole-3-carboxylic acid Natural products OC(=O)C=1C=CNC=1 DOYOPBSXEIZLRE-UHFFFAOYSA-N 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 230000005586 smoking cessation Effects 0.000 description 1
- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229940075554 sorbate Drugs 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000012289 standard assay Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 208000005057 thyrotoxicosis Diseases 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
- 230000002747 voluntary effect Effects 0.000 description 1
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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/12—Antidiarrhoeals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/06—Antiabortive agents; Labour repressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/10—Anti-acne agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/32—Alcohol-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/34—Tobacco-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/36—Opioid-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
- A61P9/06—Antiarrhythmics
-
- 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
- A61P9/10—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
-
- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Endocrinology (AREA)
- Pain & Pain Management (AREA)
- Reproductive Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Gynecology & Obstetrics (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Urology & Nephrology (AREA)
- Pregnancy & Childbirth (AREA)
- Psychology (AREA)
- Pulmonology (AREA)
- Hospice & Palliative Care (AREA)
- Dermatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Child & Adolescent Psychology (AREA)
- Vascular Medicine (AREA)
- Emergency Medicine (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US67471105P | 2005-04-26 | 2005-04-26 | |
| US60/674,711 | 2005-04-26 | ||
| DKPA200500612 | 2005-04-26 | ||
| DKPA200500612 | 2005-04-26 | ||
| PCT/EP2006/061773 WO2006114400A1 (en) | 2005-04-26 | 2006-04-24 | Novel oxadiazole derivatives and their medical use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2606087A1 true CA2606087A1 (en) | 2006-11-02 |
Family
ID=36697471
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002606087A Abandoned CA2606087A1 (en) | 2005-04-26 | 2006-04-24 | Novel oxadiazole derivatives and their medical use |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US8017631B2 (enExample) |
| EP (1) | EP1881979B1 (enExample) |
| JP (1) | JP2008539195A (enExample) |
| KR (1) | KR20080000622A (enExample) |
| AT (1) | ATE477253T1 (enExample) |
| AU (1) | AU2006239418A1 (enExample) |
| CA (1) | CA2606087A1 (enExample) |
| IL (1) | IL186360A0 (enExample) |
| MX (1) | MX2007013263A (enExample) |
| NO (1) | NO20076036L (enExample) |
| RU (1) | RU2007139255A (enExample) |
| WO (1) | WO2006114400A1 (enExample) |
Families Citing this family (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7790757B2 (en) | 1998-06-16 | 2010-09-07 | Targacept, Inc. | Compounds capable of activating cholinergic receptors |
| US8580842B2 (en) | 2003-09-30 | 2013-11-12 | Abbott Gmbh & Co. Kg | Heteroaryl-substituted 1,3-dihydroindol-2-one derivatives and medicaments containing them |
| US7459469B2 (en) | 2004-11-10 | 2008-12-02 | Targacept, Inc. | Hydroxybenzoate salts of metanicotine compounds |
| IL169855A (en) * | 2005-07-25 | 2014-05-28 | Elta Systems Ltd | A system and method for locating a receiver location |
| PL1907382T3 (pl) | 2005-07-26 | 2016-01-29 | Bial Portela & Ca Sa | Pochodne nitrokatecholowe jako inhibitory COMT |
| EP1845097A1 (en) | 2006-04-10 | 2007-10-17 | Portela & Ca., S.A. | Oxadiazole derivatives as COMT inhibitors |
| EP2255848A3 (en) * | 2006-09-04 | 2011-04-06 | NeuroSearch AS | Pharmaceutical combinations of a nicotine receptor modulator and a cognitive enhancer |
| MY149853A (en) | 2006-09-07 | 2013-10-31 | Actelion Pharmaceuticals Ltd | Pyridin-4-yl derivatives as immunomodulating agents |
| TWI408139B (zh) | 2006-09-07 | 2013-09-11 | Actelion Pharmaceuticals Ltd | 新穎噻吩衍生物 |
| CL2007002594A1 (es) | 2006-09-08 | 2008-06-06 | Actelion Pharmaceuticals Ltd | Compuestos derivados de piridin-3-il, agentes inmunomoduladores; composicion farmaceutica que comprende a dicho compuesto; y uso del compuesto en el tratamiento de enfermedades asociadas con un sistema inmunologico activado. . |
| KR20090051774A (ko) | 2006-09-21 | 2009-05-22 | 액테리온 파마슈티칼 리미티드 | 페닐 유도체 및 면역조절제로서 이들의 용도 |
| DE102006050516A1 (de) * | 2006-10-26 | 2008-04-30 | Bayer Healthcare Ag | Substituierte Dihydropyrazolone und ihre Verwendung |
| US8486979B2 (en) * | 2006-12-12 | 2013-07-16 | Abbvie Inc. | 1,2,4 oxadiazole compounds and methods of use thereof |
| US20080167286A1 (en) * | 2006-12-12 | 2008-07-10 | Abbott Laboratories | Pharmaceutical compositions and their methods of use |
| UY30846A1 (es) * | 2006-12-30 | 2008-07-31 | Abbott Gmbh & Amp | Derivados de oxindol sustituidos, medicamentos que los comprenden y uso de los mismos |
| CA2678391C (en) | 2007-01-31 | 2017-01-17 | David Alexander Learmonth | Dosage regimen for comt inhibitors |
| DK2125797T3 (da) | 2007-03-16 | 2014-02-10 | Actelion Pharmaceuticals Ltd | Aminopyridinderivater som s1p1/edg1-receptoragonister |
| WO2009023721A1 (en) | 2007-08-13 | 2009-02-19 | Divergence, Inc. | Compositions and methods for controlling nematodes |
| KR101541558B1 (ko) | 2007-08-17 | 2015-08-03 | 액테리온 파마슈티칼 리미티드 | Ｓ1ｐ1/ｅｄｇ1 수용체 조절제로서의 피리딘 유도체 |
| US20090170842A1 (en) * | 2007-11-14 | 2009-07-02 | University Of Kansas | Brca1-based breast or ovarian cancer prevention agents and methods of use |
| 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 |
| JP5701607B2 (ja) | 2007-12-07 | 2015-04-15 | 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 | アミドメチル置換オキシインドール誘導体およびバソプレッシン依存性疾患の治療へのこれらの使用 |
| US9023854B2 (en) | 2007-12-07 | 2015-05-05 | AbbVie Deutschland GmbH & Co. KG | 5-halogen-substituted oxindole derivatives and use thereof for treating vasopressin-dependent diseases |
| WO2010009775A1 (de) | 2007-12-07 | 2010-01-28 | Abbott Gmbh & Co. Kg | Carbamat-substituierte oxindol-derivate und ihre verwendung zur behandlung von vasopressin-abhängigen erkrankungen |
| CA2706834A1 (en) | 2007-12-10 | 2009-06-18 | Actelion Pharmaceuticals Ltd | Thiophene derivatives as agonists of s1p1/edg1 |
| BRPI0908340A2 (pt) * | 2008-02-28 | 2018-12-26 | Bial Portela & Ca Sa | composição farmacêutica para fármacos pouco solúveis |
| EP2262782B1 (en) | 2008-03-07 | 2012-07-04 | Actelion Pharmaceuticals Ltd. | Novel aminomethyl benzene derivatives |
| RU2010139315A (ru) | 2008-03-17 | 2012-04-27 | Биал - Портела Энд Ка., С.А. (Pt) | Кристаллические формы 5-[3-(2,5-дихлор-4,6-диметил-1-окси-пиридин-3-ил)[1,2,4]оксадиазол-5-ил]-3-нитробензол-1,2-диола |
| US8383658B2 (en) | 2008-06-04 | 2013-02-26 | Abbott Laboratories | Isoxazole based neuronal nicotinic receptor ligands and methods of use |
| CA2725573A1 (en) * | 2008-06-06 | 2009-12-10 | Abbott Laboratories | Novel 1,2,4 oxadiazole compounds and methods of use thereof |
| CA2735773A1 (en) * | 2008-09-02 | 2010-03-11 | Neurosearch A/S | Triazole derivatives and their use as nicotinic acetylcholine receptor modulators |
| WO2010035915A1 (en) * | 2008-09-25 | 2010-04-01 | 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 |
| WO2010093650A2 (en) | 2009-02-10 | 2010-08-19 | Divergence, Inc. | Compositions and methods for controlling nematodes |
| US20120095056A1 (en) * | 2009-03-19 | 2012-04-19 | Neurosearch A/S | 2,5-disubstituted tetrazole derivatives and their use as nicotinic acetylcholine receptor modulators |
| RU2701731C2 (ru) | 2009-04-01 | 2019-10-01 | Биал-Портела Энд Ка, С.А. | Фармацевтические препараты, содержащие производные нитрокатехина, и способы их получения |
| EP2435080A2 (en) | 2009-05-29 | 2012-04-04 | 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 |
| CA2767585C (en) | 2009-07-16 | 2017-09-26 | Actelion Pharmaceuticals Ltd | Pyridin-4-yl derivatives |
| BR112012029326A2 (pt) | 2010-05-20 | 2017-08-08 | Astrazeneca Ab | processo para a preparação de animais olefínicas substituídas por arila |
| WO2012076704A2 (en) | 2010-12-10 | 2012-06-14 | Basf Se | Pyrazole compounds for controlling invertebrate pests |
| MX350009B (es) | 2011-01-19 | 2017-08-23 | Idorsia Pharmaceuticals Ltd | Derivados de 2-metoxi-piridin-4-ilo. |
| US20140045900A1 (en) | 2011-02-11 | 2014-02-13 | Bial-Portela & Ca, S.A. | Administration regime for nitrocatechols |
| EP3604299B1 (en) | 2011-12-13 | 2023-07-26 | Bial-Portela & CA, S.A. | Chemical compound useful as intermediate for preparing a catechol-0-methyl transferase inhibitor |
| UA118254C2 (uk) | 2012-12-04 | 2018-12-26 | Монсанто Текнолоджи Ллс | Нематоцидні водні композиції концентрату суспензії |
| JP2018500300A (ja) | 2014-11-28 | 2018-01-11 | ノヴィファーマ，エス．アー． | パーキンソン病を遅延させるための医薬 |
| KR102220848B1 (ko) | 2015-05-20 | 2021-02-26 | 이도르시아 파마슈티컬스 리미티드 | 화합물 (s)-3-｛4-[5-(2-시클로펜틸-6-메톡시-피리딘-4-일)-[1,2,4]옥사디아졸-3-일]-2-에틸-6-메틸-페녹시｝-프로판-1,2-디올의 결정형 |
| EP3412151B1 (en) | 2016-02-01 | 2024-01-17 | Sumitomo Chemical Company, Limited | Pest control composition and pest control method |
| 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 |
| CN114585360B (zh) * | 2019-09-05 | 2025-04-29 | 特维娜有限公司 | 使用其治疗癫痫的方法 |
| WO2022200364A1 (en) | 2021-03-25 | 2022-09-29 | Syngenta Crop Protection Ag | Insect, acarina and nematode pest control |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3211742A (en) * | 1962-04-17 | 1965-10-12 | Union Carbide Corp | Process for preparing oxadiazoles |
| US3647809A (en) * | 1968-04-26 | 1972-03-07 | Chinoin Gyogyszer Es Vegyeszet | Certain pyridyl-1 2 4-oxadiazole derivatives |
| 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 |
| US4022901A (en) * | 1975-03-05 | 1977-05-10 | E. R. Squibb & Sons, Inc. | 3-Pyridinyl-5-isothiocyanophenyl oxadiazoles |
| 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 |
| US5817679A (en) | 1993-04-01 | 1998-10-06 | University Of Virginia | 7-Azabicyclo 2.2.1!-heptane and -heptene derivatives as cholinergic receptor ligands |
| US6060473A (en) | 1993-04-01 | 2000-05-09 | Ucb S.A. - Dtb | 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 |
| US6660753B2 (en) * | 1999-08-19 | 2003-12-09 | Nps Pharmaceuticals, Inc. | Heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists |
| EP1406632A4 (en) | 2001-06-08 | 2009-11-04 | Cytovia Inc | SUBSTITUTED 3-ARYL-5-ARYL-1,2,4-OXADIAZOLE AND ANALOGUE AS ACTIVATORS OF CASPASES AND APOPTOSIS INDUCTORS AND THEIR USE |
| 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 |
| EP1581213A4 (en) * | 2002-12-18 | 2008-11-19 | Cytovia Inc | 3,5-DISUBSTITUTED 1,2,4-OXADIAZOLE AND ANALOGUE TO ACTIVATE CASPASE AND INTRODUCTION OF APOPTOSIS AND THEIR USE |
| GB0303503D0 (en) | 2003-02-14 | 2003-03-19 | Novartis Ag | Organic compounds |
| WO2004110351A2 (en) * | 2003-05-14 | 2004-12-23 | Anadys Pharmaceuticals, Inc. | Heterocyclic compounds for treating hepatitis c virus |
| US20060252741A1 (en) | 2003-05-15 | 2006-11-09 | Colandrea Vincent J | 3-(2-amino-1-azacyclyl)-5-aryl-1,2,4-oxadiazoles as s1p receptor agonists |
| CN1859908A (zh) | 2003-10-01 | 2006-11-08 | 默克公司 | 作为s1p受体激动剂的3,5－芳基、杂芳基或环烷基取代的－1,2,4－噁二唑类化合物 |
| CA2547198A1 (en) | 2003-12-17 | 2005-06-30 | Merck & Co., Inc. | (3,4-disubstituted)propanoic carboxylates as s1p (edg) receptor agonists |
-
2006
- 2006-04-24 AU AU2006239418A patent/AU2006239418A1/en not_active Abandoned
- 2006-04-24 CA CA002606087A patent/CA2606087A1/en not_active Abandoned
- 2006-04-24 RU RU2007139255/04A patent/RU2007139255A/ru not_active Application Discontinuation
- 2006-04-24 KR KR1020077024814A patent/KR20080000622A/ko not_active Withdrawn
- 2006-04-24 MX MX2007013263A patent/MX2007013263A/es not_active Application Discontinuation
- 2006-04-24 AT AT06754801T patent/ATE477253T1/de not_active IP Right Cessation
- 2006-04-24 US US11/919,146 patent/US8017631B2/en not_active Expired - Fee Related
- 2006-04-24 EP EP06754801A patent/EP1881979B1/en active Active
- 2006-04-24 WO PCT/EP2006/061773 patent/WO2006114400A1/en not_active Ceased
- 2006-04-24 JP JP2008508201A patent/JP2008539195A/ja active Pending
-
2007
- 2007-10-07 IL IL186360A patent/IL186360A0/en unknown
- 2007-11-23 NO NO20076036A patent/NO20076036L/no not_active Application Discontinuation
-
2011
- 2011-07-29 US US13/194,193 patent/US20110294856A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| IL186360A0 (en) | 2008-01-20 |
| AU2006239418A1 (en) | 2006-11-02 |
| EP1881979B1 (en) | 2010-08-11 |
| US20110294856A1 (en) | 2011-12-01 |
| WO2006114400A1 (en) | 2006-11-02 |
| ATE477253T1 (de) | 2010-08-15 |
| US8017631B2 (en) | 2011-09-13 |
| US20090312347A1 (en) | 2009-12-17 |
| KR20080000622A (ko) | 2008-01-02 |
| RU2007139255A (ru) | 2009-06-10 |
| EP1881979A1 (en) | 2008-01-30 |
| JP2008539195A (ja) | 2008-11-13 |
| MX2007013263A (es) | 2008-01-22 |
| NO20076036L (no) | 2007-11-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US8017631B2 (en) | Oxadiazole derivatives and their medical use | |
| TWI417100B (zh) | 二唑衍生物及其作為代謝型麩胺酸受體增效劑-８４２之用途 | |
| US20100029685A1 (en) | Oxadiazole and thiadiazole compounds and their use as nicotinic acetylcholine receptor modulators | |
| US8637510B2 (en) | Morpholinothiazoles as alpha 7 positive allosteric modulators | |
| JP2021506760A (ja) | モノアシルグリセロールリパーゼ阻害剤として有用なベンゾオキサジン誘導体 | |
| US9802927B2 (en) | Oxadiazine compounds and methods of use thereof | |
| JP2010523654A (ja) | 複素環化合物およびその使用方法 | |
| EP1833804A1 (en) | Aryl sulphonamide modulators | |
| CN110234638A (zh) | 杂芳基苯氧基苯甲酰胺kappa阿片类配体 | |
| JP2019531326A (ja) | ナフチリジノン誘導体および不整脈の治療におけるそれらの使用 | |
| KR20130122531A (ko) | Ｍｇｌｕｒ５ 양성 알로스테릭 조절물로서 치환된 ６메틸니코틴아미드 | |
| US20070293497A1 (en) | 2,3,4,6-Substituted Pyridyl Derivative Compounds Useful As Beta-Secretase Inhibitors For The Treatment Of Alzheimer's Disease | |
| JP3012338B2 (ja) | アリールおよびヘテロアリールアルコキシナフタレン誘導体 | |
| CN111107846A (zh) | 烟碱乙酰胆碱受体的杂芳基变构调节剂 | |
| EP4463452B1 (en) | C-myc mrna translation modulators and uses thereof in the treatment of cancer | |
| CN114786771A (zh) | 作为lpa受体2抑制剂的喹唑啉衍生物 | |
| KR20090069183A (ko) | 옥사디아졸 및 티아디아졸 화합물 및 니코틴성 아세틸콜린 수용체 조절제로서의 이들의 용도 | |
| JP5057982B2 (ja) | ヒスタミンｈ３受容体阻害剤、製造及び治療的使用 | |
| CN101166735A (zh) | 新颖的二唑衍生物及其医药应用 | |
| US7902201B2 (en) | Isoxazolo-pyrazine derivatives | |
| RU2338746C2 (ru) | Новые диазабициклические арильные производные, содержащие их фармацевтические композиции и их применение | |
| HK1117503A (en) | Novel oxadiazole derivatives and their medical use | |
| CA2592321A1 (en) | Nicotinic acetylcholine receptor ligands | |
| HK40068822A (en) | Quinazoline derivatives as lpa receptor 2 inhibitors | |
| HK1137757A (en) | Oxadiazole and thiadiazole compounds and their use as nicotinic acetylcholine receptor modulators |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued | ||
| FZDE | Discontinued |
Effective date: 20110426 |