JP2009542683A - D−アミノ酸オキシダーゼの縮合ヘテロ環式阻害剤 - Google Patents
D−アミノ酸オキシダーゼの縮合ヘテロ環式阻害剤 Download PDFInfo
- Publication number
- JP2009542683A JP2009542683A JP2009518342A JP2009518342A JP2009542683A JP 2009542683 A JP2009542683 A JP 2009542683A JP 2009518342 A JP2009518342 A JP 2009518342A JP 2009518342 A JP2009518342 A JP 2009518342A JP 2009542683 A JP2009542683 A JP 2009542683A
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- unsubstituted
- member selected
- alkyl
- heterocycloalkyl
- 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.)
- Pending
Links
- 102000004674 D-amino-acid oxidase Human genes 0.000 title abstract description 33
- 108010003989 D-amino-acid oxidase Proteins 0.000 title abstract description 33
- 239000003112 inhibitor Substances 0.000 title abstract description 12
- 125000000623 heterocyclic group Chemical group 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 328
- 238000000034 method Methods 0.000 claims abstract description 152
- 208000002193 Pain Diseases 0.000 claims abstract description 103
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 94
- 230000036407 pain Effects 0.000 claims abstract description 81
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 70
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 57
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 43
- 208000035475 disorder Diseases 0.000 claims abstract description 35
- 230000004770 neurodegeneration Effects 0.000 claims abstract description 22
- 206010010904 Convulsion Diseases 0.000 claims abstract description 20
- 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 19
- 208000012902 Nervous system disease Diseases 0.000 claims abstract description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 14
- 230000036461 convulsion Effects 0.000 claims abstract description 13
- 208000025966 Neurological disease Diseases 0.000 claims abstract description 11
- 206010003591 Ataxia Diseases 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 120
- 125000003118 aryl group Chemical group 0.000 claims description 108
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 102
- 125000001072 heteroaryl group Chemical group 0.000 claims description 92
- 229910052739 hydrogen Inorganic materials 0.000 claims description 84
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 78
- 229910052731 fluorine Inorganic materials 0.000 claims description 68
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 56
- 150000002500 ions Chemical class 0.000 claims description 52
- MTCFGRXMJLQNBG-UWTATZPHSA-N D-Serine Chemical compound OC[C@@H](N)C(O)=O MTCFGRXMJLQNBG-UWTATZPHSA-N 0.000 claims description 43
- 229930195711 D-Serine Natural products 0.000 claims description 43
- 229910052801 chlorine Inorganic materials 0.000 claims description 42
- 229910052794 bromium Inorganic materials 0.000 claims description 38
- 150000003839 salts Chemical class 0.000 claims description 38
- 229910052727 yttrium Inorganic materials 0.000 claims description 37
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 31
- 208000004296 neuralgia Diseases 0.000 claims description 30
- 208000021722 neuropathic pain Diseases 0.000 claims description 30
- 229910052799 carbon Inorganic materials 0.000 claims description 28
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 28
- 125000002252 acyl group Chemical group 0.000 claims description 27
- 125000004429 atom Chemical group 0.000 claims description 23
- 239000000651 prodrug Substances 0.000 claims description 22
- 229940002612 prodrug Drugs 0.000 claims description 22
- 201000010099 disease Diseases 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 201000000980 schizophrenia Diseases 0.000 claims description 20
- 125000003342 alkenyl group Chemical group 0.000 claims description 19
- 150000002367 halogens Chemical class 0.000 claims description 18
- 208000024827 Alzheimer disease Diseases 0.000 claims description 17
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 125000005647 linker group Chemical group 0.000 claims description 11
- 208000023890 Complex Regional Pain Syndromes Diseases 0.000 claims description 10
- HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 claims description 10
- 125000004122 cyclic group Chemical group 0.000 claims description 10
- 239000003937 drug carrier Substances 0.000 claims description 10
- 208000030507 AIDS Diseases 0.000 claims description 9
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims description 9
- 230000002981 neuropathic effect Effects 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 206010036376 Postherpetic Neuralgia Diseases 0.000 claims description 8
- 150000001767 cationic compounds Chemical class 0.000 claims description 8
- 230000001684 chronic effect Effects 0.000 claims description 8
- 150000002892 organic cations Chemical class 0.000 claims description 8
- 206010044652 trigeminal neuralgia Diseases 0.000 claims description 7
- 208000004983 Phantom Limb Diseases 0.000 claims description 6
- 206010056238 Phantom pain Diseases 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 208000020431 spinal cord injury Diseases 0.000 claims description 6
- 208000018737 Parkinson disease Diseases 0.000 claims description 5
- 206010058019 Cancer Pain Diseases 0.000 claims description 4
- DYDCUQKUCUHJBH-UWTATZPHSA-N D-Cycloserine Chemical compound N[C@@H]1CONC1=O DYDCUQKUCUHJBH-UWTATZPHSA-N 0.000 claims description 4
- DYDCUQKUCUHJBH-UHFFFAOYSA-N D-Cycloserine Natural products NC1CONC1=O DYDCUQKUCUHJBH-UHFFFAOYSA-N 0.000 claims description 4
- 208000001640 Fibromyalgia Diseases 0.000 claims description 4
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 3
- 230000005062 synaptic transmission Effects 0.000 claims description 3
- 208000008035 Back Pain Diseases 0.000 claims description 2
- 208000019695 Migraine disease Diseases 0.000 claims description 2
- 150000004677 hydrates Chemical class 0.000 claims description 2
- 206010027599 migraine Diseases 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 229910052789 astatine Inorganic materials 0.000 claims 1
- 229960003077 cycloserine Drugs 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 369
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 286
- 230000015572 biosynthetic process Effects 0.000 description 185
- 238000003786 synthesis reaction Methods 0.000 description 183
- 239000000203 mixture Substances 0.000 description 104
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 99
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 96
- -1 (cyclohexyl) methyl Chemical group 0.000 description 90
- 239000007787 solid Substances 0.000 description 87
- 239000000243 solution Substances 0.000 description 85
- 238000006243 chemical reaction Methods 0.000 description 61
- 238000003818 flash chromatography Methods 0.000 description 61
- 238000000746 purification Methods 0.000 description 60
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 59
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 58
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 56
- 238000011282 treatment Methods 0.000 description 54
- 238000010898 silica gel chromatography Methods 0.000 description 52
- 239000000460 chlorine Substances 0.000 description 51
- 238000004128 high performance liquid chromatography Methods 0.000 description 50
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 46
- 238000012360 testing method Methods 0.000 description 44
- 239000000741 silica gel Substances 0.000 description 42
- 229910002027 silica gel Inorganic materials 0.000 description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 42
- 238000005481 NMR spectroscopy Methods 0.000 description 37
- 230000000694 effects Effects 0.000 description 37
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 35
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 34
- 230000015654 memory Effects 0.000 description 32
- 239000000047 product Substances 0.000 description 31
- 239000011734 sodium Substances 0.000 description 31
- 125000001424 substituent group Chemical group 0.000 description 30
- 230000013016 learning Effects 0.000 description 27
- 239000003921 oil Substances 0.000 description 26
- 239000011541 reaction mixture Substances 0.000 description 26
- 239000012267 brine Substances 0.000 description 25
- 235000019198 oils Nutrition 0.000 description 25
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 25
- 239000012043 crude product Substances 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- 238000003756 stirring Methods 0.000 description 23
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 22
- 208000024891 symptom Diseases 0.000 description 22
- 241001465754 Metazoa Species 0.000 description 21
- 230000006378 damage Effects 0.000 description 21
- 238000009472 formulation Methods 0.000 description 20
- 208000004454 Hyperalgesia Diseases 0.000 description 19
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 19
- 150000001299 aldehydes Chemical class 0.000 description 19
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 17
- 238000002953 preparative HPLC Methods 0.000 description 17
- 208000000044 Amnesia Diseases 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 239000002253 acid Substances 0.000 description 16
- 239000000543 intermediate Substances 0.000 description 16
- 239000012044 organic layer Substances 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 16
- 208000000094 Chronic Pain Diseases 0.000 description 15
- 150000002148 esters Chemical class 0.000 description 15
- 206010012289 Dementia Diseases 0.000 description 14
- 102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 description 14
- 108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 description 14
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 14
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 14
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 14
- 208000010877 cognitive disease Diseases 0.000 description 14
- 239000003814 drug Substances 0.000 description 14
- 238000000105 evaporative light scattering detection Methods 0.000 description 14
- 208000014674 injury Diseases 0.000 description 14
- RLKHFSNWQCZBDC-UHFFFAOYSA-N n-(benzenesulfonyl)-n-fluorobenzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)N(F)S(=O)(=O)C1=CC=CC=C1 RLKHFSNWQCZBDC-UHFFFAOYSA-N 0.000 description 14
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- 229910052777 Praseodymium Inorganic materials 0.000 description 13
- 208000027418 Wounds and injury Diseases 0.000 description 13
- 210000004556 brain Anatomy 0.000 description 13
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- 239000000706 filtrate Substances 0.000 description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
- 239000000725 suspension Substances 0.000 description 13
- 208000031091 Amnestic disease Diseases 0.000 description 12
- 208000035154 Hyperesthesia Diseases 0.000 description 12
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 230000001965 increasing effect Effects 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 206010027175 memory impairment Diseases 0.000 description 12
- WRHZVMBBRYBTKZ-UHFFFAOYSA-N pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC=CN1 WRHZVMBBRYBTKZ-UHFFFAOYSA-N 0.000 description 12
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 12
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 11
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 description 11
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
- 230000006986 amnesia Effects 0.000 description 11
- 235000019253 formic acid Nutrition 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
- 229920006395 saturated elastomer Polymers 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- MFGHPIAIHLKMBC-UHFFFAOYSA-N 4-[(4-chlorophenyl)methyl]thiophene-2-carbaldehyde Chemical compound C1=CC(Cl)=CC=C1CC1=CSC(C=O)=C1 MFGHPIAIHLKMBC-UHFFFAOYSA-N 0.000 description 10
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 description 10
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- 206010015037 epilepsy Diseases 0.000 description 10
- 230000006870 function Effects 0.000 description 10
- 230000008569 process Effects 0.000 description 10
- CNIVWXIXRNMAHJ-UHFFFAOYSA-N 3-methyl-4h-thieno[3,2-b]pyrrole-5-carboxylic acid Chemical compound C1=C(C(O)=O)NC2=C1SC=C2C CNIVWXIXRNMAHJ-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 9
- 230000006735 deficit Effects 0.000 description 9
- 229940079593 drug Drugs 0.000 description 9
- 239000000284 extract Substances 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 230000005764 inhibitory process Effects 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- 238000007127 saponification reaction Methods 0.000 description 9
- 230000035807 sensation Effects 0.000 description 9
- 235000019615 sensations Nutrition 0.000 description 9
- 208000011580 syndromic disease Diseases 0.000 description 9
- 230000001154 acute effect Effects 0.000 description 8
- 208000005298 acute pain Diseases 0.000 description 8
- 206010053552 allodynia Diseases 0.000 description 8
- 238000004587 chromatography analysis Methods 0.000 description 8
- 230000008434 fear extinction Effects 0.000 description 8
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 230000002085 persistent effect Effects 0.000 description 8
- 150000003233 pyrroles Chemical class 0.000 description 8
- 102000005962 receptors Human genes 0.000 description 8
- 108020003175 receptors Proteins 0.000 description 8
- 238000007363 ring formation reaction Methods 0.000 description 8
- 239000012453 solvate Substances 0.000 description 8
- 229930192474 thiophene Natural products 0.000 description 8
- PMHDSACGRKBACK-UHFFFAOYSA-N 4h-thieno[3,2-b]pyrrole-5-carboxylic acid Chemical compound S1C=CC2=C1C=C(C(=O)O)N2 PMHDSACGRKBACK-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 7
- 208000019901 Anxiety disease Diseases 0.000 description 7
- 208000028698 Cognitive impairment Diseases 0.000 description 7
- PAEYAKGINDQUCT-UHFFFAOYSA-N Ethyl 2-pyrrolecarboxylate Chemical compound CCOC(=O)C1=CC=CN1 PAEYAKGINDQUCT-UHFFFAOYSA-N 0.000 description 7
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- HCUARRIEZVDMPT-UHFFFAOYSA-N Indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 description 7
- 208000006011 Stroke Diseases 0.000 description 7
- 125000002947 alkylene group Chemical group 0.000 description 7
- 238000003556 assay Methods 0.000 description 7
- 210000003169 central nervous system Anatomy 0.000 description 7
- BJDCWCLMFKKGEE-CMDXXVQNSA-N chembl252518 Chemical compound C([C@@](OO1)(C)O2)C[C@H]3[C@H](C)CC[C@@H]4[C@@]31[C@@H]2O[C@H](O)[C@@H]4C BJDCWCLMFKKGEE-CMDXXVQNSA-N 0.000 description 7
- 238000009833 condensation Methods 0.000 description 7
- 230000005494 condensation Effects 0.000 description 7
- 230000004064 dysfunction Effects 0.000 description 7
- 239000011737 fluorine Substances 0.000 description 7
- 239000004615 ingredient Substances 0.000 description 7
- 230000014759 maintenance of location Effects 0.000 description 7
- 239000012299 nitrogen atmosphere Substances 0.000 description 7
- 208000033808 peripheral neuropathy Diseases 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 230000006977 prepulse inhibition Effects 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 230000004044 response Effects 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- 238000004809 thin layer chromatography Methods 0.000 description 7
- 239000003981 vehicle Substances 0.000 description 7
- PPXUUPXQWDQNGO-UHFFFAOYSA-N 2-azidoacetic acid Chemical compound OC(=O)CN=[N+]=[N-] PPXUUPXQWDQNGO-UHFFFAOYSA-N 0.000 description 6
- AFEBFEJAYWJLIR-UHFFFAOYSA-N 2-chloro-4h-furo[3,2-b]pyrrole-5-carboxylic acid Chemical compound O1C(Cl)=CC2=C1C=C(C(=O)O)N2 AFEBFEJAYWJLIR-UHFFFAOYSA-N 0.000 description 6
- OWJRYNILRVVVFK-UHFFFAOYSA-N 2-chloro-4h-thieno[3,2-b]pyrrole-5-carboxylic acid Chemical compound S1C(Cl)=CC2=C1C=C(C(=O)O)N2 OWJRYNILRVVVFK-UHFFFAOYSA-N 0.000 description 6
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 6
- HNROXXPBCUVOKZ-UHFFFAOYSA-N 2-methyl-4h-thieno[3,2-b]pyrrole-5-carboxylic acid Chemical compound N1C(C(O)=O)=CC2=C1C=C(C)S2 HNROXXPBCUVOKZ-UHFFFAOYSA-N 0.000 description 6
- NPHIFZXNCDKIAW-IHWYPQMZSA-N 3-[(z)-prop-1-enyl]-4h-furo[3,2-b]pyrrole-5-carboxylic acid Chemical compound C1=C(C(O)=O)NC2=C1OC=C2\C=C/C NPHIFZXNCDKIAW-IHWYPQMZSA-N 0.000 description 6
- VIERWJYIMVJYBQ-UHFFFAOYSA-N 3-formyl-4h-furo[3,2-b]pyrrole-5-carboxylic acid Chemical compound O1C=C(C=O)C2=C1C=C(C(=O)O)N2 VIERWJYIMVJYBQ-UHFFFAOYSA-N 0.000 description 6
- PCVIGYOOZPUNSI-UHFFFAOYSA-N 5-[(4-chlorophenyl)methyl]thiophene-2-carbaldehyde Chemical compound C1=CC(Cl)=CC=C1CC1=CC=C(C=O)S1 PCVIGYOOZPUNSI-UHFFFAOYSA-N 0.000 description 6
- 241000282412 Homo Species 0.000 description 6
- 208000026139 Memory disease Diseases 0.000 description 6
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- 230000036506 anxiety Effects 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 230000019771 cognition Effects 0.000 description 6
- 230000001149 cognitive effect Effects 0.000 description 6
- 230000003750 conditioning effect Effects 0.000 description 6
- 230000003247 decreasing effect Effects 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- KRPJGLCVEYTVBW-UHFFFAOYSA-N ethyl 6h-thieno[2,3-b]pyrrole-5-carboxylate Chemical compound C1=CSC2=C1C=C(C(=O)OCC)N2 KRPJGLCVEYTVBW-UHFFFAOYSA-N 0.000 description 6
- 210000003414 extremity Anatomy 0.000 description 6
- 125000001153 fluoro group Chemical group F* 0.000 description 6
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical class O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 6
- 229910001411 inorganic cation Inorganic materials 0.000 description 6
- 210000000653 nervous system Anatomy 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 6
- 230000002093 peripheral effect Effects 0.000 description 6
- 230000002265 prevention Effects 0.000 description 6
- 230000009467 reduction Effects 0.000 description 6
- 230000002829 reductive effect Effects 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- 230000001225 therapeutic effect Effects 0.000 description 6
- MKNMFJGDGQHMER-UHFFFAOYSA-N 1-methyl-4h-pyrrolo[3,2-b]pyrrole-5-carboxylic acid Chemical compound N1C(C(O)=O)=CC2=C1C=CN2C MKNMFJGDGQHMER-UHFFFAOYSA-N 0.000 description 5
- WZMNTSZIYSQDAN-UHFFFAOYSA-N 2-bromo-4h-furo[3,2-b]pyrrole-5-carboxylic acid Chemical compound O1C(Br)=CC2=C1C=C(C(=O)O)N2 WZMNTSZIYSQDAN-UHFFFAOYSA-N 0.000 description 5
- MDPWNOVTUQUEHP-UHFFFAOYSA-N 2-fluoro-4h-thieno[3,2-b]pyrrole-5-carboxylic acid Chemical compound S1C(F)=CC2=C1C=C(C(=O)O)N2 MDPWNOVTUQUEHP-UHFFFAOYSA-N 0.000 description 5
- GRTOFBWMOOTRLU-UHFFFAOYSA-N 3-bromo-4h-furo[3,2-b]pyrrole-5-carboxylic acid Chemical compound O1C=C(Br)C2=C1C=C(C(=O)O)N2 GRTOFBWMOOTRLU-UHFFFAOYSA-N 0.000 description 5
- UZISGOJIMQYLOK-UHFFFAOYSA-N 3-ethenyl-4h-furo[3,2-b]pyrrole-5-carboxylic acid Chemical compound O1C=C(C=C)C2=C1C=C(C(=O)O)N2 UZISGOJIMQYLOK-UHFFFAOYSA-N 0.000 description 5
- JOZWNDJXSGKSIE-UHFFFAOYSA-N 4-(2-phenylethyl)thiophene-2-carbaldehyde Chemical compound S1C(C=O)=CC(CCC=2C=CC=CC=2)=C1 JOZWNDJXSGKSIE-UHFFFAOYSA-N 0.000 description 5
- MMAIBGHDBYQYDI-UHFFFAOYSA-N 4h-furo[3,2-b]pyrrole-5-carboxylic acid Chemical compound O1C=CC2=C1C=C(C(=O)O)N2 MMAIBGHDBYQYDI-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 208000013586 Complex regional pain syndrome type 1 Diseases 0.000 description 5
- 102000004190 Enzymes Human genes 0.000 description 5
- 108090000790 Enzymes Proteins 0.000 description 5
- 206010020751 Hypersensitivity Diseases 0.000 description 5
- 206010065390 Inflammatory pain Diseases 0.000 description 5
- 235000019502 Orange oil Nutrition 0.000 description 5
- 201000001947 Reflex Sympathetic Dystrophy Diseases 0.000 description 5
- 238000006069 Suzuki reaction reaction Methods 0.000 description 5
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 5
- 230000002159 abnormal effect Effects 0.000 description 5
- 208000026935 allergic disease Diseases 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 230000027455 binding Effects 0.000 description 5
- 210000001638 cerebellum Anatomy 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000012230 colorless oil Substances 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- 230000003111 delayed effect Effects 0.000 description 5
- 238000010511 deprotection reaction Methods 0.000 description 5
- 238000003745 diagnosis Methods 0.000 description 5
- 238000010828 elution Methods 0.000 description 5
- 229940088598 enzyme Drugs 0.000 description 5
- 125000004185 ester group Chemical group 0.000 description 5
- UMMMPHUCNBOYFZ-UHFFFAOYSA-N ethyl 4-chloro-6h-thieno[2,3-b]pyrrole-5-carboxylate Chemical compound S1C=CC2=C1NC(C(=O)OCC)=C2Cl UMMMPHUCNBOYFZ-UHFFFAOYSA-N 0.000 description 5
- 125000004494 ethyl ester group Chemical group 0.000 description 5
- 238000003682 fluorination reaction Methods 0.000 description 5
- 125000004474 heteroalkylene group Chemical group 0.000 description 5
- 238000000338 in vitro Methods 0.000 description 5
- 238000001727 in vivo Methods 0.000 description 5
- 230000002757 inflammatory effect Effects 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 5
- 230000006984 memory degeneration Effects 0.000 description 5
- 208000023060 memory loss Diseases 0.000 description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- VONGYFFEWFJHNP-UHFFFAOYSA-N methyl 1h-pyrrole-2-carboxylate Chemical compound COC(=O)C1=CC=CN1 VONGYFFEWFJHNP-UHFFFAOYSA-N 0.000 description 5
- 210000005036 nerve Anatomy 0.000 description 5
- 210000002569 neuron Anatomy 0.000 description 5
- 239000010502 orange oil Substances 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 5
- 239000012363 selectfluor Substances 0.000 description 5
- 150000003577 thiophenes Chemical class 0.000 description 5
- XGCDBGRZEKYHNV-UHFFFAOYSA-N 1,1-bis(diphenylphosphino)methane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CP(C=1C=CC=CC=1)C1=CC=CC=C1 XGCDBGRZEKYHNV-UHFFFAOYSA-N 0.000 description 4
- RORQKWXGJVJJRX-UHFFFAOYSA-N 1-benzyl-4h-pyrrolo[3,2-b]pyrrole-5-carboxylic acid Chemical compound C1=CC=2NC(C(=O)O)=CC=2N1CC1=CC=CC=C1 RORQKWXGJVJJRX-UHFFFAOYSA-N 0.000 description 4
- MREIFUWKYMNYTK-UHFFFAOYSA-N 1H-pyrrole Chemical class C=1C=CNC=1.C=1C=CNC=1 MREIFUWKYMNYTK-UHFFFAOYSA-N 0.000 description 4
- CKPLXHJFZJDLLJ-UHFFFAOYSA-N 2-(2-phenylethyl)-4h-thieno[3,2-b]pyrrole-5-carboxylic acid Chemical compound C=1C=2NC(C(=O)O)=CC=2SC=1CCC1=CC=CC=C1 CKPLXHJFZJDLLJ-UHFFFAOYSA-N 0.000 description 4
- QYINWXAPIIBHHF-UHFFFAOYSA-N 2-(2-phenylethyl)-6h-thieno[2,3-b]pyrrole-5-carboxylic acid Chemical compound S1C=2NC(C(=O)O)=CC=2C=C1CCC1=CC=CC=C1 QYINWXAPIIBHHF-UHFFFAOYSA-N 0.000 description 4
- SCKHGUSFTMZCQF-UHFFFAOYSA-N 2-[(4-chlorophenyl)methyl]-4h-thieno[3,2-b]pyrrole-5-carboxylic acid Chemical compound C=1C=2NC(C(=O)O)=CC=2SC=1CC1=CC=C(Cl)C=C1 SCKHGUSFTMZCQF-UHFFFAOYSA-N 0.000 description 4
- FVCMFZXIIQKSRR-UHFFFAOYSA-N 2-[(4-chlorophenyl)methyl]-6h-thieno[2,3-b]pyrrole-5-carboxylic acid Chemical compound S1C=2NC(C(=O)O)=CC=2C=C1CC1=CC=C(Cl)C=C1 FVCMFZXIIQKSRR-UHFFFAOYSA-N 0.000 description 4
- OFYWMXKWLYRDTQ-UHFFFAOYSA-N 2-bromo-4h-thieno[3,2-b]pyrrole-5-carboxylic acid Chemical compound S1C(Br)=CC2=C1C=C(C(=O)O)N2 OFYWMXKWLYRDTQ-UHFFFAOYSA-N 0.000 description 4
- XAFRVVYPVBHBMA-UHFFFAOYSA-N 2-bromo-6h-thieno[2,3-b]pyrrole-5-carboxylic acid Chemical compound C1=C(Br)SC2=C1C=C(C(=O)O)N2 XAFRVVYPVBHBMA-UHFFFAOYSA-N 0.000 description 4
- YJHHTOLIHBFPMF-UHFFFAOYSA-N 2-fluoro-6h-thieno[2,3-b]pyrrole-5-carboxylic acid Chemical compound C1=C(F)SC2=C1C=C(C(=O)O)N2 YJHHTOLIHBFPMF-UHFFFAOYSA-N 0.000 description 4
- OHKSQQOKYBCIQE-UHFFFAOYSA-N 3-(2-phenylethyl)-4h-thieno[3,2-b]pyrrole-5-carboxylic acid Chemical compound C1=2NC(C(=O)O)=CC=2SC=C1CCC1=CC=CC=C1 OHKSQQOKYBCIQE-UHFFFAOYSA-N 0.000 description 4
- VLXSPKGTKZBELQ-UHFFFAOYSA-N 3-(trifluoromethyl)-4h-furo[3,2-b]pyrrole-5-carboxylic acid Chemical compound O1C=C(C(F)(F)F)C2=C1C=C(C(=O)O)N2 VLXSPKGTKZBELQ-UHFFFAOYSA-N 0.000 description 4
- SWTPUPKFKYYOEM-UHFFFAOYSA-N 3-[(4-chlorophenyl)methyl]-6h-thieno[2,3-b]pyrrole-5-carboxylic acid Chemical compound C=1SC=2NC(C(=O)O)=CC=2C=1CC1=CC=C(Cl)C=C1 SWTPUPKFKYYOEM-UHFFFAOYSA-N 0.000 description 4
- VJXSERLPOOWZGU-VOTSOKGWSA-N 3-[(e)-2-phenylethenyl]-4h-furo[3,2-b]pyrrole-5-carboxylic acid Chemical compound C1=2NC(C(=O)O)=CC=2OC=C1\C=C\C1=CC=CC=C1 VJXSERLPOOWZGU-VOTSOKGWSA-N 0.000 description 4
- WOCVITYACZJEKA-UHFFFAOYSA-N 3-[2-(4-chlorophenyl)ethyl]-6h-thieno[2,3-b]pyrrole-5-carboxylic acid Chemical compound C=1SC=2NC(C(=O)O)=CC=2C=1CCC1=CC=C(Cl)C=C1 WOCVITYACZJEKA-UHFFFAOYSA-N 0.000 description 4
- MLINZILODAUEOR-UHFFFAOYSA-N 3-benzyl-6h-thieno[2,3-b]pyrrole-5-carboxylic acid Chemical compound C=1SC=2NC(C(=O)O)=CC=2C=1CC1=CC=CC=C1 MLINZILODAUEOR-UHFFFAOYSA-N 0.000 description 4
- WQGQGYADKDKACG-UHFFFAOYSA-N 3-bromo-4h-thieno[3,2-b]pyrrole-5-carboxylic acid Chemical compound S1C=C(Br)C2=C1C=C(C(=O)O)N2 WQGQGYADKDKACG-UHFFFAOYSA-N 0.000 description 4
- BFQKWXMSMYDJQT-UHFFFAOYSA-N 3-bromo-6h-thieno[2,3-b]pyrrole-5-carboxylic acid Chemical compound BrC1=CSC2=C1C=C(C(=O)O)N2 BFQKWXMSMYDJQT-UHFFFAOYSA-N 0.000 description 4
- FDGNVONVURZBLL-UHFFFAOYSA-N 3-chloro-4h-thieno[3,2-b]pyrrole-5-carboxylic acid Chemical compound S1C=C(Cl)C2=C1C=C(C(=O)O)N2 FDGNVONVURZBLL-UHFFFAOYSA-N 0.000 description 4
- KFHSHROQKJEWRI-UHFFFAOYSA-N 3-cyano-4h-furo[3,2-b]pyrrole-5-carboxylic acid Chemical compound O1C=C(C#N)C2=C1C=C(C(=O)O)N2 KFHSHROQKJEWRI-UHFFFAOYSA-N 0.000 description 4
- IQTCTGHOLXRCLZ-UHFFFAOYSA-N 3-cyclopropyl-4h-furo[3,2-b]pyrrole-5-carboxylic acid Chemical compound C1=2NC(C(=O)O)=CC=2OC=C1C1CC1 IQTCTGHOLXRCLZ-UHFFFAOYSA-N 0.000 description 4
- IDGWVERCOKPLPJ-UHFFFAOYSA-N 3-ethyl-4h-furo[3,2-b]pyrrole-5-carboxylic acid Chemical compound C1=C(C(O)=O)NC2=C1OC=C2CC IDGWVERCOKPLPJ-UHFFFAOYSA-N 0.000 description 4
- URRUSJVVVSKZSH-UHFFFAOYSA-N 3-fluoro-4h-furo[3,2-b]pyrrole-5-carboxylic acid Chemical compound O1C=C(F)C2=C1C=C(C(=O)O)N2 URRUSJVVVSKZSH-UHFFFAOYSA-N 0.000 description 4
- IMVSZFMGQMCNCV-UHFFFAOYSA-N 3-fluoro-4h-thieno[3,2-b]pyrrole-5-carboxylic acid Chemical compound S1C=C(F)C2=C1C=C(C(=O)O)N2 IMVSZFMGQMCNCV-UHFFFAOYSA-N 0.000 description 4
- POTNAEUKCBDAGH-UHFFFAOYSA-N 3-fluoro-6h-thieno[2,3-b]pyrrole-5-carboxylic acid Chemical compound FC1=CSC2=C1C=C(C(=O)O)N2 POTNAEUKCBDAGH-UHFFFAOYSA-N 0.000 description 4
- OOWPYBCJKPNETK-UHFFFAOYSA-N 3-methyl-4h-furo[3,2-b]pyrrole-5-carboxylic acid Chemical compound C1=C(C(O)=O)NC2=C1OC=C2C OOWPYBCJKPNETK-UHFFFAOYSA-N 0.000 description 4
- ARWYYJPZHRRUSX-UHFFFAOYSA-N 3-phenyl-6h-thieno[2,3-b]pyrrole-5-carboxylic acid Chemical compound C=1SC=2NC(C(=O)O)=CC=2C=1C1=CC=CC=C1 ARWYYJPZHRRUSX-UHFFFAOYSA-N 0.000 description 4
- SAYKNBQCVYQQJF-UHFFFAOYSA-N 4-(2-phenylethynyl)thiophene-2-carbaldehyde Chemical compound S1C(C=O)=CC(C#CC=2C=CC=CC=2)=C1 SAYKNBQCVYQQJF-UHFFFAOYSA-N 0.000 description 4
- HTEXKHXVQFVUDB-UHFFFAOYSA-N 4-[2-(4-chlorophenyl)ethyl]thiophene-3-carbaldehyde Chemical compound C1=CC(Cl)=CC=C1CCC1=CSC=C1C=O HTEXKHXVQFVUDB-UHFFFAOYSA-N 0.000 description 4
- ZYSQCKYCBRQBHZ-UHFFFAOYSA-N 4-fluorofuran-2-carbaldehyde Chemical compound FC1=COC(C=O)=C1 ZYSQCKYCBRQBHZ-UHFFFAOYSA-N 0.000 description 4
- CBMDSKURMHSKDR-UHFFFAOYSA-N 5-(2-phenylethyl)thiophene-2-carbaldehyde Chemical compound S1C(C=O)=CC=C1CCC1=CC=CC=C1 CBMDSKURMHSKDR-UHFFFAOYSA-N 0.000 description 4
- AYWGPLNIWWJDBT-UHFFFAOYSA-N 6-bromo-4h-thieno[3,2-b]pyrrole-5-carboxylic acid Chemical compound C1=CSC2=C1NC(C(=O)O)=C2Br AYWGPLNIWWJDBT-UHFFFAOYSA-N 0.000 description 4
- UQSQOFVPIABDDO-UHFFFAOYSA-N 6-fluoro-4h-thieno[3,2-b]pyrrole-5-carboxylic acid Chemical compound C1=CSC2=C1NC(C(=O)O)=C2F UQSQOFVPIABDDO-UHFFFAOYSA-N 0.000 description 4
- XWKVOVYOCKXSKA-UHFFFAOYSA-N 6-methyl-4h-thieno[3,2-b]pyrrole-5-carboxylic acid Chemical compound C1=CSC2=C1NC(C(O)=O)=C2C XWKVOVYOCKXSKA-UHFFFAOYSA-N 0.000 description 4
- 208000001387 Causalgia Diseases 0.000 description 4
- 208000018652 Closed Head injury Diseases 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- 208000030814 Eating disease Diseases 0.000 description 4
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 4
- 208000019454 Feeding and Eating disease Diseases 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- 206010021143 Hypoxia Diseases 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 206010034912 Phobia Diseases 0.000 description 4
- 208000028017 Psychotic disease Diseases 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 239000000556 agonist Substances 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 238000010171 animal model Methods 0.000 description 4
- 239000000164 antipsychotic agent Substances 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 230000006399 behavior Effects 0.000 description 4
- 230000009286 beneficial effect Effects 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 201000011510 cancer Diseases 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 230000006999 cognitive decline Effects 0.000 description 4
- 208000014439 complex regional pain syndrome type 2 Diseases 0.000 description 4
- 230000001143 conditioned effect Effects 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 235000014632 disordered eating Nutrition 0.000 description 4
- ADEBPBSSDYVVLD-UHFFFAOYSA-N donepezil Chemical compound O=C1C=2C=C(OC)C(OC)=CC=2CC1CC(CC1)CCN1CC1=CC=CC=C1 ADEBPBSSDYVVLD-UHFFFAOYSA-N 0.000 description 4
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 4
- YUIDGONLMDUWNF-UHFFFAOYSA-N ethyl 3-chloro-4h-thieno[3,2-b]pyrrole-5-carboxylate Chemical compound S1C=C(Cl)C2=C1C=C(C(=O)OCC)N2 YUIDGONLMDUWNF-UHFFFAOYSA-N 0.000 description 4
- PBTSJBSYRNYTCI-UHFFFAOYSA-N ethyl 4-bromo-6h-thieno[2,3-b]pyrrole-5-carboxylate Chemical compound S1C=CC2=C1NC(C(=O)OCC)=C2Br PBTSJBSYRNYTCI-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 4
- 230000009610 hypersensitivity Effects 0.000 description 4
- 230000007954 hypoxia Effects 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- 230000004054 inflammatory process Effects 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 4
- 230000007246 mechanism Effects 0.000 description 4
- 150000004702 methyl esters Chemical class 0.000 description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
- POTVAILTNPOQJH-UHFFFAOYSA-N n,n-dimethyl-1-(5-phenylmethoxy-1h-indol-3-yl)methanamine Chemical compound C1=C2C(CN(C)C)=CNC2=CC=C1OCC1=CC=CC=C1 POTVAILTNPOQJH-UHFFFAOYSA-N 0.000 description 4
- 201000001119 neuropathy Diseases 0.000 description 4
- 230000007823 neuropathy Effects 0.000 description 4
- 231100000189 neurotoxic Toxicity 0.000 description 4
- 230000002887 neurotoxic effect Effects 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 208000019899 phobic disease Diseases 0.000 description 4
- 208000028173 post-traumatic stress disease Diseases 0.000 description 4
- BKZMULQSKYPQRC-UHFFFAOYSA-M potassium;1-benzyl-4h-pyrrolo[3,2-b]pyrrole-5-carboxylate Chemical compound [K+].C1=CC=2NC(C(=O)[O-])=CC=2N1CC1=CC=CC=C1 BKZMULQSKYPQRC-UHFFFAOYSA-M 0.000 description 4
- SFTRZXKYZFWBAW-UHFFFAOYSA-M potassium;1-methyl-4h-pyrrolo[3,2-b]pyrrole-5-carboxylate Chemical compound [K+].N1C(C([O-])=O)=CC2=C1C=CN2C SFTRZXKYZFWBAW-UHFFFAOYSA-M 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 230000011514 reflex Effects 0.000 description 4
- 239000012047 saturated solution Substances 0.000 description 4
- 230000000451 tissue damage Effects 0.000 description 4
- 231100000827 tissue damage Toxicity 0.000 description 4
- 230000000472 traumatic effect Effects 0.000 description 4
- 208000009935 visceral pain Diseases 0.000 description 4
- SZRNBGXUGVUETL-UHFFFAOYSA-N (4-bromo-4,4-difluorobut-2-ynoxy)-tert-butyl-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)OCC#CC(F)(F)Br SZRNBGXUGVUETL-UHFFFAOYSA-N 0.000 description 3
- LVLCWVAVXNPOFF-UHFFFAOYSA-N (4-formylthiophen-3-yl)boronic acid Chemical compound OB(O)C1=CSC=C1C=O LVLCWVAVXNPOFF-UHFFFAOYSA-N 0.000 description 3
- WFZGXAGXMGHOBY-UHFFFAOYSA-N 1-(2-phenylethyl)pyrazole-4-carbaldehyde Chemical compound C1=C(C=O)C=NN1CCC1=CC=CC=C1 WFZGXAGXMGHOBY-UHFFFAOYSA-N 0.000 description 3
- WOXHPHOZJMLUFE-UHFFFAOYSA-N 1-benzylpyrazole-4-carbaldehyde Chemical compound C1=C(C=O)C=NN1CC1=CC=CC=C1 WOXHPHOZJMLUFE-UHFFFAOYSA-N 0.000 description 3
- JNHZZTKKFSPICX-UHFFFAOYSA-N 1-benzylpyrrole-2-carbaldehyde Chemical compound O=CC1=CC=CN1CC1=CC=CC=C1 JNHZZTKKFSPICX-UHFFFAOYSA-N 0.000 description 3
- MMQJZQKFTWIATR-UHFFFAOYSA-N 1h-pyrazole;1h-pyrrole Chemical class C=1C=CNC=1.C=1C=NNC=1 MMQJZQKFTWIATR-UHFFFAOYSA-N 0.000 description 3
- ZAMFMWOTDLEXLY-UHFFFAOYSA-N 1h-pyrrole;1,3-thiazole Chemical class C=1C=CNC=1.C1=CSC=N1 ZAMFMWOTDLEXLY-UHFFFAOYSA-N 0.000 description 3
- FJOHEVFGRJBAIJ-UHFFFAOYSA-N 2,3-dibromo-4h-thieno[3,2-b]pyrrole-5-carboxylic acid Chemical compound S1C(Br)=C(Br)C2=C1C=C(C(=O)O)N2 FJOHEVFGRJBAIJ-UHFFFAOYSA-N 0.000 description 3
- GVSQRFNIXVGOQE-UHFFFAOYSA-N 2-(trifluoromethyl)-4h-furo[3,2-b]pyrrole-5-carboxylic acid Chemical compound O1C(C(F)(F)F)=CC2=C1C=C(C(=O)O)N2 GVSQRFNIXVGOQE-UHFFFAOYSA-N 0.000 description 3
- NXSJJTSIZPKKMM-UHFFFAOYSA-N 2-benzyl-4h-furo[3,2-b]pyrrole-5-carboxylic acid Chemical compound C=1C=2NC(C(=O)O)=CC=2OC=1CC1=CC=CC=C1 NXSJJTSIZPKKMM-UHFFFAOYSA-N 0.000 description 3
- UKKYTLNKHZLUJR-UHFFFAOYSA-N 2-fluoro-4h-furo[3,2-b]pyrrole-5-carboxylic acid Chemical compound O1C(F)=CC2=C1C=C(C(=O)O)N2 UKKYTLNKHZLUJR-UHFFFAOYSA-N 0.000 description 3
- ILLLWINWDFYWES-UHFFFAOYSA-N 2-methyl-4h-furo[3,2-b]pyrrole-5-carboxylic acid Chemical compound N1C(C(O)=O)=CC2=C1C=C(C)O2 ILLLWINWDFYWES-UHFFFAOYSA-N 0.000 description 3
- CUCMYHOPTSUPIM-UHFFFAOYSA-N 3-(2-phenylethyl)-4h-furo[3,2-b]pyrrole-5-carboxylic acid Chemical compound C1=2NC(C(=O)O)=CC=2OC=C1CCC1=CC=CC=C1 CUCMYHOPTSUPIM-UHFFFAOYSA-N 0.000 description 3
- KUYFPJWLZXCSOC-UHFFFAOYSA-N 3-(hydroxymethyl)-4h-furo[3,2-b]pyrrole-5-carboxylic acid Chemical compound C1=C(C(O)=O)NC2=C1OC=C2CO KUYFPJWLZXCSOC-UHFFFAOYSA-N 0.000 description 3
- JFPMXKAHUZNTHW-UHFFFAOYSA-N 3-[(4-chlorophenyl)methyl]-4h-thieno[3,2-b]pyrrole-5-carboxylic acid Chemical compound C1=2NC(C(=O)O)=CC=2SC=C1CC1=CC=C(Cl)C=C1 JFPMXKAHUZNTHW-UHFFFAOYSA-N 0.000 description 3
- ILODFLMZZKTIDM-UHFFFAOYSA-N 3-benzyl-4h-furo[3,2-b]pyrrole-5-carboxylic acid Chemical compound C1=2NC(C(=O)O)=CC=2OC=C1CC1=CC=CC=C1 ILODFLMZZKTIDM-UHFFFAOYSA-N 0.000 description 3
- HDPBBBQTCSOYSB-UHFFFAOYSA-N 3-chloro-4h-furo[3,2-b]pyrrole-5-carboxylic acid Chemical compound O1C=C(Cl)C2=C1C=C(C(=O)O)N2 HDPBBBQTCSOYSB-UHFFFAOYSA-N 0.000 description 3
- ZJEUUASQEZMUNP-UHFFFAOYSA-N 3-propan-2-yl-4h-furo[3,2-b]pyrrole-5-carboxylic acid Chemical compound C1=C(C(O)=O)NC2=C1OC=C2C(C)C ZJEUUASQEZMUNP-UHFFFAOYSA-N 0.000 description 3
- SUAKVCDYDUALQH-UHFFFAOYSA-N 4-(2-phenylethyl)furan-2-carbaldehyde Chemical compound O1C(C=O)=CC(CCC=2C=CC=CC=2)=C1 SUAKVCDYDUALQH-UHFFFAOYSA-N 0.000 description 3
- HZXKGUWZFQJRBG-UHFFFAOYSA-N 4-(trifluoromethyl)furan-2-carbaldehyde Chemical compound FC(F)(F)C1=COC(C=O)=C1 HZXKGUWZFQJRBG-UHFFFAOYSA-N 0.000 description 3
- HHZQGWSGBIVHSL-UHFFFAOYSA-N 4-[(4-chlorophenyl)methyl]thiophene-3-carbaldehyde Chemical compound C1=CC(Cl)=CC=C1CC1=CSC=C1C=O HHZQGWSGBIVHSL-UHFFFAOYSA-N 0.000 description 3
- DBPMTQBXPQFOHN-VOTSOKGWSA-N 4-[(e)-2-phenylethenyl]furan-2-carbaldehyde Chemical compound O1C(C=O)=CC(\C=C\C=2C=CC=CC=2)=C1 DBPMTQBXPQFOHN-VOTSOKGWSA-N 0.000 description 3
- KEXIUNXGSUAMNN-UHFFFAOYSA-N 4-benzylfuran-2-carbaldehyde Chemical compound O1C(C=O)=CC(CC=2C=CC=CC=2)=C1 KEXIUNXGSUAMNN-UHFFFAOYSA-N 0.000 description 3
- MOKRBDCJFCISEK-UHFFFAOYSA-N 4-benzylthiophene-3-carbaldehyde Chemical compound O=CC1=CSC=C1CC1=CC=CC=C1 MOKRBDCJFCISEK-UHFFFAOYSA-N 0.000 description 3
- OONJRWDQJMBPMF-UHFFFAOYSA-N 4-bromo-6h-thieno[2,3-b]pyrrole-5-carboxylic acid Chemical compound S1C=CC2=C1NC(C(=O)O)=C2Br OONJRWDQJMBPMF-UHFFFAOYSA-N 0.000 description 3
- MRGBBKQOSUHKPF-UHFFFAOYSA-N 4-bromofuran-2-carbaldehyde Chemical compound BrC1=COC(C=O)=C1 MRGBBKQOSUHKPF-UHFFFAOYSA-N 0.000 description 3
- GZNONFRIPBEMRS-UHFFFAOYSA-N 4-cyclopropylfuran-2-carbaldehyde Chemical compound O1C(C=O)=CC(C2CC2)=C1 GZNONFRIPBEMRS-UHFFFAOYSA-N 0.000 description 3
- PPVKGKYHKXSMLK-UHFFFAOYSA-N 4-ethenylfuran-2-carbaldehyde Chemical compound C=CC1=COC(C=O)=C1 PPVKGKYHKXSMLK-UHFFFAOYSA-N 0.000 description 3
- BLHZUMDWLLFLJC-UHFFFAOYSA-N 4-methylfuran-2-carbaldehyde Chemical compound CC1=COC(C=O)=C1 BLHZUMDWLLFLJC-UHFFFAOYSA-N 0.000 description 3
- OGLXWEVJNNKWJY-UHFFFAOYSA-N 4-o-tert-butyl 5-o-methyl 2-bromofuro[3,2-b]pyrrole-4,5-dicarboxylate Chemical compound O1C(Br)=CC2=C1C=C(C(=O)OC)N2C(=O)OC(C)(C)C OGLXWEVJNNKWJY-UHFFFAOYSA-N 0.000 description 3
- RNFIHRJWAKWIEM-UHFFFAOYSA-N 4-propan-2-ylfuran-2-carbaldehyde Chemical compound CC(C)C1=COC(C=O)=C1 RNFIHRJWAKWIEM-UHFFFAOYSA-N 0.000 description 3
- DFUTWTAXOYDQRR-UHFFFAOYSA-N 5-(2-phenylethyl)thiophene-3-carbaldehyde Chemical compound O=CC1=CSC(CCC=2C=CC=CC=2)=C1 DFUTWTAXOYDQRR-UHFFFAOYSA-N 0.000 description 3
- MMRIITDPKNWJQI-VOTSOKGWSA-N 5-[(e)-2-phenylethenyl]thiophene-3-carbaldehyde Chemical compound O=CC1=CSC(\C=C\C=2C=CC=CC=2)=C1 MMRIITDPKNWJQI-VOTSOKGWSA-N 0.000 description 3
- IRNAKAVXOUFQTN-UHFFFAOYSA-N 5-[tert-butyl(dimethyl)silyl]oxy-2,2-difluoropent-3-yn-1-ol Chemical compound CC(C)(C)[Si](C)(C)OCC#CC(F)(F)CO IRNAKAVXOUFQTN-UHFFFAOYSA-N 0.000 description 3
- BEMMSXOPWRZIOY-UHFFFAOYSA-N 5-benzylfuran-2-carbaldehyde Chemical compound O1C(C=O)=CC=C1CC1=CC=CC=C1 BEMMSXOPWRZIOY-UHFFFAOYSA-N 0.000 description 3
- KURANAVGCJMDFR-UHFFFAOYSA-N 5-fluorothiophene-2-carbaldehyde Chemical compound FC1=CC=C(C=O)S1 KURANAVGCJMDFR-UHFFFAOYSA-N 0.000 description 3
- OVIQOPYSEFRDMV-UHFFFAOYSA-N 6-bromo-4h-furo[3,2-b]pyrrole-5-carboxylic acid Chemical compound C1=COC2=C1NC(C(=O)O)=C2Br OVIQOPYSEFRDMV-UHFFFAOYSA-N 0.000 description 3
- KHBZGQNVVAXNLK-UHFFFAOYSA-N 6-fluoro-4h-furo[3,2-b]pyrrole-5-carboxylic acid Chemical compound C1=COC2=C1NC(C(=O)O)=C2F KHBZGQNVVAXNLK-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 206010003805 Autism Diseases 0.000 description 3
- 208000020706 Autistic disease Diseases 0.000 description 3
- 208000017667 Chronic Disease Diseases 0.000 description 3
- 206010012239 Delusion Diseases 0.000 description 3
- 208000004547 Hallucinations Diseases 0.000 description 3
- 206010019196 Head injury Diseases 0.000 description 3
- 208000023105 Huntington disease Diseases 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 206010061218 Inflammation Diseases 0.000 description 3
- 108090000862 Ion Channels Proteins 0.000 description 3
- 102000004310 Ion Channels Human genes 0.000 description 3
- 238000012347 Morris Water Maze Methods 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- 208000000112 Myalgia Diseases 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- 208000028389 Nerve injury Diseases 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 108010006152 Serine racemase Proteins 0.000 description 3
- 102100035717 Serine racemase Human genes 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001241 acetals Chemical class 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 229940005529 antipsychotics Drugs 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- 150000001642 boronic acid derivatives Chemical class 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 150000001733 carboxylic acid esters Chemical class 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 208000015114 central nervous system disease Diseases 0.000 description 3
- 206010008118 cerebral infarction Diseases 0.000 description 3
- 238000002512 chemotherapy Methods 0.000 description 3
- 239000000544 cholinesterase inhibitor Substances 0.000 description 3
- 230000003920 cognitive function Effects 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 231100000868 delusion Toxicity 0.000 description 3
- IPKKHRVROFYTEK-UHFFFAOYSA-N dipentyl phthalate Chemical compound CCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCC IPKKHRVROFYTEK-UHFFFAOYSA-N 0.000 description 3
- VDCSGNNYCFPWFK-UHFFFAOYSA-N diphenylsilane Chemical compound C=1C=CC=CC=1[SiH2]C1=CC=CC=C1 VDCSGNNYCFPWFK-UHFFFAOYSA-N 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- YGSOAUAHZCWHPK-UHFFFAOYSA-N ethyl 2,3-dibromo-4h-thieno[3,2-b]pyrrole-5-carboxylate Chemical compound S1C(Br)=C(Br)C2=C1C=C(C(=O)OCC)N2 YGSOAUAHZCWHPK-UHFFFAOYSA-N 0.000 description 3
- RBTYQWWFSZMUBD-UHFFFAOYSA-N ethyl 2-(2-phenylethyl)-6h-thieno[2,3-b]pyrrole-5-carboxylate Chemical compound S1C=2NC(C(=O)OCC)=CC=2C=C1CCC1=CC=CC=C1 RBTYQWWFSZMUBD-UHFFFAOYSA-N 0.000 description 3
- DBUKGGCXHSFKQP-UHFFFAOYSA-N ethyl 2-(trifluoromethyl)-4h-furo[3,2-b]pyrrole-5-carboxylate Chemical compound O1C(C(F)(F)F)=CC2=C1C=C(C(=O)OCC)N2 DBUKGGCXHSFKQP-UHFFFAOYSA-N 0.000 description 3
- FOZNVCOTXKVHFH-UHFFFAOYSA-N ethyl 2-[(4-chlorophenyl)methyl]-4h-thieno[3,2-b]pyrrole-5-carboxylate Chemical compound C=1C=2NC(C(=O)OCC)=CC=2SC=1CC1=CC=C(Cl)C=C1 FOZNVCOTXKVHFH-UHFFFAOYSA-N 0.000 description 3
- NGPHTFGJRRQKMI-UHFFFAOYSA-N ethyl 2-[(4-chlorophenyl)methyl]-6h-thieno[2,3-b]pyrrole-5-carboxylate Chemical compound S1C=2NC(C(=O)OCC)=CC=2C=C1CC1=CC=C(Cl)C=C1 NGPHTFGJRRQKMI-UHFFFAOYSA-N 0.000 description 3
- LVFGFBHCDFCWEN-UHFFFAOYSA-N ethyl 2-azidoprop-2-enoate Chemical compound CCOC(=O)C(=C)N=[N+]=[N-] LVFGFBHCDFCWEN-UHFFFAOYSA-N 0.000 description 3
- BSIIENSVDCHCBF-UHFFFAOYSA-N ethyl 2-chloro-4h-furo[3,2-b]pyrrole-5-carboxylate Chemical compound O1C(Cl)=CC2=C1C=C(C(=O)OCC)N2 BSIIENSVDCHCBF-UHFFFAOYSA-N 0.000 description 3
- ZIGXACGLYBHAFH-UHFFFAOYSA-N ethyl 2-fluoro-4h-thieno[3,2-b]pyrrole-5-carboxylate Chemical compound S1C(F)=CC2=C1C=C(C(=O)OCC)N2 ZIGXACGLYBHAFH-UHFFFAOYSA-N 0.000 description 3
- PDHKWZKPXDTJKJ-UHFFFAOYSA-N ethyl 3-(trifluoromethyl)-4h-furo[3,2-b]pyrrole-5-carboxylate Chemical compound O1C=C(C(F)(F)F)C2=C1C=C(C(=O)OCC)N2 PDHKWZKPXDTJKJ-UHFFFAOYSA-N 0.000 description 3
- VCEXEVDIFDQLIB-UHFFFAOYSA-N ethyl 3-[(4-chlorophenyl)methyl]-4h-thieno[3,2-b]pyrrole-5-carboxylate Chemical compound C1=2NC(C(=O)OCC)=CC=2SC=C1CC1=CC=C(Cl)C=C1 VCEXEVDIFDQLIB-UHFFFAOYSA-N 0.000 description 3
- AVBZZXGZHWTTQG-UHFFFAOYSA-N ethyl 3-[(4-chlorophenyl)methyl]-6h-thieno[2,3-b]pyrrole-5-carboxylate Chemical compound C=1SC=2NC(C(=O)OCC)=CC=2C=1CC1=CC=C(Cl)C=C1 AVBZZXGZHWTTQG-UHFFFAOYSA-N 0.000 description 3
- OOWDCGMCFQICNN-CMDGGOBGSA-N ethyl 3-[(e)-2-phenylethenyl]-4h-furo[3,2-b]pyrrole-5-carboxylate Chemical compound C1=2NC(C(=O)OCC)=CC=2OC=C1\C=C\C1=CC=CC=C1 OOWDCGMCFQICNN-CMDGGOBGSA-N 0.000 description 3
- IMJNTKCUAGEOAO-UHFFFAOYSA-N ethyl 3-[2-(4-chlorophenyl)ethyl]-6h-thieno[2,3-b]pyrrole-5-carboxylate Chemical compound C=1SC=2NC(C(=O)OCC)=CC=2C=1CCC1=CC=C(Cl)C=C1 IMJNTKCUAGEOAO-UHFFFAOYSA-N 0.000 description 3
- KSONMHNRMJQMFE-UHFFFAOYSA-N ethyl 3-bromo-4h-thieno[3,2-b]pyrrole-5-carboxylate Chemical compound S1C=C(Br)C2=C1C=C(C(=O)OCC)N2 KSONMHNRMJQMFE-UHFFFAOYSA-N 0.000 description 3
- CKZIDWJZAWLTDL-UHFFFAOYSA-N ethyl 3-cyclopropyl-4h-furo[3,2-b]pyrrole-5-carboxylate Chemical compound C1=2NC(C(=O)OCC)=CC=2OC=C1C1CC1 CKZIDWJZAWLTDL-UHFFFAOYSA-N 0.000 description 3
- FAXBFZSAJISWGE-UHFFFAOYSA-N ethyl 3-ethenyl-4h-furo[3,2-b]pyrrole-5-carboxylate Chemical compound O1C=C(C=C)C2=C1C=C(C(=O)OCC)N2 FAXBFZSAJISWGE-UHFFFAOYSA-N 0.000 description 3
- MXGZRIGYSQKECK-UHFFFAOYSA-N ethyl 3-ethyl-4h-furo[3,2-b]pyrrole-5-carboxylate Chemical compound O1C=C(CC)C2=C1C=C(C(=O)OCC)N2 MXGZRIGYSQKECK-UHFFFAOYSA-N 0.000 description 3
- WXBHZKGCCLZUGI-UHFFFAOYSA-N ethyl 3-fluoro-4h-thieno[3,2-b]pyrrole-5-carboxylate Chemical compound S1C=C(F)C2=C1C=C(C(=O)OCC)N2 WXBHZKGCCLZUGI-UHFFFAOYSA-N 0.000 description 3
- IVTSDPODKGCTGY-UHFFFAOYSA-N ethyl 3-methyl-4h-thieno[3,2-b]pyrrole-5-carboxylate Chemical compound S1C=C(C)C2=C1C=C(C(=O)OCC)N2 IVTSDPODKGCTGY-UHFFFAOYSA-N 0.000 description 3
- HQUBIVPIDNGDEQ-UHFFFAOYSA-N ethyl 3-propan-2-yl-4h-furo[3,2-b]pyrrole-5-carboxylate Chemical compound O1C=C(C(C)C)C2=C1C=C(C(=O)OCC)N2 HQUBIVPIDNGDEQ-UHFFFAOYSA-N 0.000 description 3
- NNABKJKQNGGLKM-UHFFFAOYSA-N ethyl 4h-furo[3,2-b]pyrrole-5-carboxylate Chemical compound O1C=CC2=C1C=C(C(=O)OCC)N2 NNABKJKQNGGLKM-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 210000001508 eye Anatomy 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 238000007429 general method Methods 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 208000028867 ischemia Diseases 0.000 description 3
- 230000008449 language Effects 0.000 description 3
- 201000003723 learning disability Diseases 0.000 description 3
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 230000008897 memory decline Effects 0.000 description 3
- NJMHLPYIHMAHRE-UHFFFAOYSA-N methyl 2-methyl-4h-furo[3,2-b]pyrrole-5-carboxylate Chemical compound O1C(C)=CC2=C1C=C(C(=O)OC)N2 NJMHLPYIHMAHRE-UHFFFAOYSA-N 0.000 description 3
- FBCFZDRUYPHONP-UHFFFAOYSA-N methyl 3-fluoro-6h-thieno[2,3-b]pyrrole-5-carboxylate Chemical compound FC1=CSC2=C1C=C(C(=O)OC)N2 FBCFZDRUYPHONP-UHFFFAOYSA-N 0.000 description 3
- LIIJOCBTGRORSY-UHFFFAOYSA-N methyl 4h-furo[3,2-b]pyrrole-5-carboxylate Chemical compound O1C=CC2=C1C=C(C(=O)OC)N2 LIIJOCBTGRORSY-UHFFFAOYSA-N 0.000 description 3
- CINAWYPBOKCJHH-UHFFFAOYSA-N methyl 6-fluoro-4h-thieno[3,2-b]pyrrole-5-carboxylate Chemical compound C1=CSC2=C1NC(C(=O)OC)=C2F CINAWYPBOKCJHH-UHFFFAOYSA-N 0.000 description 3
- BYUKOSRRSBTICX-UHFFFAOYSA-N methyl 6-methyl-4h-thieno[3,2-b]pyrrole-5-carboxylate Chemical compound C1=CSC2=C1NC(C(=O)OC)=C2C BYUKOSRRSBTICX-UHFFFAOYSA-N 0.000 description 3
- 208000031225 myocardial ischemia Diseases 0.000 description 3
- 230000008764 nerve damage Effects 0.000 description 3
- 230000008904 neural response Effects 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-dimethylbenzene Natural products CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 230000007170 pathology Effects 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 238000012746 preparative thin layer chromatography Methods 0.000 description 3
- 230000000750 progressive effect Effects 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 208000020016 psychiatric disease Diseases 0.000 description 3
- 239000003368 psychostimulant agent Substances 0.000 description 3
- DOYOPBSXEIZLRE-UHFFFAOYSA-N pyrrole-3-carboxylic acid Natural products OC(=O)C=1C=CNC=1 DOYOPBSXEIZLRE-UHFFFAOYSA-N 0.000 description 3
- 238000004007 reversed phase HPLC Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 150000003457 sulfones Chemical class 0.000 description 3
- 125000004434 sulfur atom Chemical group 0.000 description 3
- 238000013268 sustained release Methods 0.000 description 3
- 239000012730 sustained-release form Substances 0.000 description 3
- 201000008914 temporal lobe epilepsy Diseases 0.000 description 3
- 231100000331 toxic Toxicity 0.000 description 3
- 230000002588 toxic effect Effects 0.000 description 3
- HJPOQNKXQHXEKE-UHFFFAOYSA-N (1-benzylpyrazol-4-yl)methanol Chemical compound C1=C(CO)C=NN1CC1=CC=CC=C1 HJPOQNKXQHXEKE-UHFFFAOYSA-N 0.000 description 2
- JPYHYGZOZZUNGA-UHFFFAOYSA-N (1-benzylpyrrol-2-yl)methanol Chemical compound OCC1=CC=CN1CC1=CC=CC=C1 JPYHYGZOZZUNGA-UHFFFAOYSA-N 0.000 description 2
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 2
- UVTUHTQNNGCVPI-UHFFFAOYSA-N (4-fluorofuran-2-yl)methanol Chemical compound OCC1=CC(F)=CO1 UVTUHTQNNGCVPI-UHFFFAOYSA-N 0.000 description 2
- UJQNOBISTKAIPR-UHFFFAOYSA-N (4-fluorothiophen-2-yl)methanol Chemical compound OCC1=CC(F)=CS1 UJQNOBISTKAIPR-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- JEXOBLNGJXHXPS-UHFFFAOYSA-N 1-(2-phenylethyl)pyrazole Chemical compound C=1C=CC=CC=1CCN1C=CC=N1 JEXOBLNGJXHXPS-UHFFFAOYSA-N 0.000 description 2
- OUKQTRFCDKSEPL-UHFFFAOYSA-N 1-Methyl-2-pyrrolecarboxaldehyde Chemical compound CN1C=CC=C1C=O OUKQTRFCDKSEPL-UHFFFAOYSA-N 0.000 description 2
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 2
- BVQPVBZRJSFOEZ-UHFFFAOYSA-N 1-chloro-4-(diethoxyphosphorylmethyl)benzene Chemical compound CCOP(=O)(OCC)CC1=CC=C(Cl)C=C1 BVQPVBZRJSFOEZ-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- RABBMOYULJIAFU-UHFFFAOYSA-N 1h-pyrrole;thiophene Chemical class C=1C=CNC=1.C=1C=CSC=1 RABBMOYULJIAFU-UHFFFAOYSA-N 0.000 description 2
- GPWNWKWQOLEVEQ-UHFFFAOYSA-N 2,4-diaminopyrimidine-5-carbaldehyde Chemical compound NC1=NC=C(C=O)C(N)=N1 GPWNWKWQOLEVEQ-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- GNKMLUZRQKOBEF-UHFFFAOYSA-N 2-(2-phenylethyl)pyrazole-3-carbaldehyde Chemical compound O=CC1=CC=NN1CCC1=CC=CC=C1 GNKMLUZRQKOBEF-UHFFFAOYSA-N 0.000 description 2
- FZFGCHRSCIKKOX-UHFFFAOYSA-N 2-(bromomethyl)-4-(trifluoromethyl)furan Chemical compound FC(F)(F)C1=COC(CBr)=C1 FZFGCHRSCIKKOX-UHFFFAOYSA-N 0.000 description 2
- DXHCHIJMMKQRKR-UHFFFAOYSA-N 2-fluorothiophene Chemical compound FC1=CC=CS1 DXHCHIJMMKQRKR-UHFFFAOYSA-N 0.000 description 2
- WMPPDTMATNBGJN-UHFFFAOYSA-N 2-phenylethylbromide Chemical compound BrCCC1=CC=CC=C1 WMPPDTMATNBGJN-UHFFFAOYSA-N 0.000 description 2
- RBIGKSZIQCTIJF-UHFFFAOYSA-N 3-formylthiophene Chemical compound O=CC=1C=CSC=1 RBIGKSZIQCTIJF-UHFFFAOYSA-N 0.000 description 2
- TUFORXFWYVAOOP-UHFFFAOYSA-N 4-(2-phenylethynyl)furan-2-carbaldehyde Chemical compound O1C(C=O)=CC(C#CC=2C=CC=CC=2)=C1 TUFORXFWYVAOOP-UHFFFAOYSA-N 0.000 description 2
- UYHLIOFILQCDGR-UHFFFAOYSA-N 4-(2-trimethylsilylethoxymethyl)thieno[3,2-b]pyrrole-5-carboxylic acid Chemical compound S1C=CC2=C1C=C(C(O)=O)N2COCC[Si](C)(C)C UYHLIOFILQCDGR-UHFFFAOYSA-N 0.000 description 2
- ZXSVWILBEKFPJA-UHFFFAOYSA-N 4-[2-(4-chlorophenyl)ethenyl]thiophene-3-carbaldehyde Chemical compound C1=CC(Cl)=CC=C1C=CC1=CSC=C1C=O ZXSVWILBEKFPJA-UHFFFAOYSA-N 0.000 description 2
- PDONIKHDXYHTLS-UHFFFAOYSA-N 4-bromothiophene-2-carbaldehyde Chemical compound BrC1=CSC(C=O)=C1 PDONIKHDXYHTLS-UHFFFAOYSA-N 0.000 description 2
- ZDVHJQOCVBTMOF-UHFFFAOYSA-N 4-bromothiophene-3-carbaldehyde Chemical compound BrC1=CSC=C1C=O ZDVHJQOCVBTMOF-UHFFFAOYSA-N 0.000 description 2
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 2
- AAWOXRNFSSSREJ-UHFFFAOYSA-N 4-fluorothiophene-2-carbaldehyde Chemical compound FC1=CSC(C=O)=C1 AAWOXRNFSSSREJ-UHFFFAOYSA-N 0.000 description 2
- IBWSJGDUGPZUJV-UHFFFAOYSA-N 4-phenylthiophene-3-carbaldehyde Chemical compound O=CC1=CSC=C1C1=CC=CC=C1 IBWSJGDUGPZUJV-UHFFFAOYSA-N 0.000 description 2
- VOROEQBFPPIACJ-UHFFFAOYSA-N 5-Phosphononorvaline Chemical compound OC(=O)C(N)CCCP(O)(O)=O VOROEQBFPPIACJ-UHFFFAOYSA-N 0.000 description 2
- CDBAAGJKGCQYLA-UHFFFAOYSA-N 5-fluorothiophene-3-carbaldehyde Chemical compound FC1=CC(C=O)=CS1 CDBAAGJKGCQYLA-UHFFFAOYSA-N 0.000 description 2
- QJHLCUOJRLTPSI-UHFFFAOYSA-N 5-formyl-3-methylfuran-2-carboxylic acid Chemical compound CC=1C=C(C=O)OC=1C(O)=O QJHLCUOJRLTPSI-UHFFFAOYSA-N 0.000 description 2
- FYSLNKSSHFIUCC-UHFFFAOYSA-N 6-chloro-4h-furo[3,2-b]pyrrole-5-carboxylic acid Chemical compound C1=COC2=C1NC(C(=O)O)=C2Cl FYSLNKSSHFIUCC-UHFFFAOYSA-N 0.000 description 2
- IARHDLPYCCGSKT-UHFFFAOYSA-N 6-chloro-4h-thieno[3,2-b]pyrrole-5-carboxylic acid Chemical compound C1=CSC2=C1NC(C(=O)O)=C2Cl IARHDLPYCCGSKT-UHFFFAOYSA-N 0.000 description 2
- NUYPMIRKFLHBNC-UHFFFAOYSA-N 6-o-tert-butyl 5-o-ethyl 2-bromothieno[2,3-b]pyrrole-5,6-dicarboxylate Chemical compound C1=C(Br)SC2=C1C=C(C(=O)OCC)N2C(=O)OC(C)(C)C NUYPMIRKFLHBNC-UHFFFAOYSA-N 0.000 description 2
- WMMSKVADYMCPTL-UHFFFAOYSA-N 6-o-tert-butyl 5-o-ethyl thieno[2,3-b]pyrrole-5,6-dicarboxylate Chemical compound C1=CSC2=C1C=C(C(=O)OCC)N2C(=O)OC(C)(C)C WMMSKVADYMCPTL-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 208000006888 Agnosia Diseases 0.000 description 2
- 241001047040 Agnosia Species 0.000 description 2
- 241001535291 Analges Species 0.000 description 2
- 206010003062 Apraxia Diseases 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 208000027448 Attention Deficit and Disruptive Behavior disease Diseases 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- 208000020925 Bipolar disease Diseases 0.000 description 2
- 208000014644 Brain disease Diseases 0.000 description 2
- 101710155857 C-C motif chemokine 2 Proteins 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- 206010008025 Cerebellar ataxia Diseases 0.000 description 2
- 102000000018 Chemokine CCL2 Human genes 0.000 description 2
- 201000006082 Chickenpox Diseases 0.000 description 2
- 150000008569 D-serines Chemical class 0.000 description 2
- 206010011968 Decreased immune responsiveness Diseases 0.000 description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 2
- 201000010374 Down Syndrome Diseases 0.000 description 2
- 208000032274 Encephalopathy Diseases 0.000 description 2
- 208000027776 Extrapyramidal disease Diseases 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 description 2
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 239000004471 Glycine Substances 0.000 description 2
- 208000010496 Heart Arrest Diseases 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 208000020358 Learning disease Diseases 0.000 description 2
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 2
- 240000007472 Leucaena leucocephala Species 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 208000019022 Mood disease Diseases 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 206010028570 Myelopathy Diseases 0.000 description 2
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 206010028923 Neonatal asphyxia Diseases 0.000 description 2
- 208000037212 Neonatal hypoxic and ischemic brain injury Diseases 0.000 description 2
- 208000009668 Neurobehavioral Manifestations Diseases 0.000 description 2
- 208000008589 Obesity Diseases 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- 206010037779 Radiculopathy Diseases 0.000 description 2
- 206010072005 Spinal pain Diseases 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 206010046980 Varicella Diseases 0.000 description 2
- 208000036142 Viral infection Diseases 0.000 description 2
- VKIJXFIYBAYHOE-VOTSOKGWSA-N [(e)-2-phenylethenyl]boronic acid Chemical compound OB(O)\C=C\C1=CC=CC=C1 VKIJXFIYBAYHOE-VOTSOKGWSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 230000003281 allosteric effect Effects 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 229940024606 amino acid Drugs 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229940005524 anti-dementia drug Drugs 0.000 description 2
- 239000000935 antidepressant agent Substances 0.000 description 2
- 229940005513 antidepressants Drugs 0.000 description 2
- 229940054051 antipsychotic indole derivative Drugs 0.000 description 2
- 201000007201 aphasia Diseases 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 238000002820 assay format Methods 0.000 description 2
- 230000035045 associative learning Effects 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 2
- OBXSGRKNCOCTTM-UHFFFAOYSA-N benzyl diethyl phosphate Chemical compound CCOP(=O)(OCC)OCC1=CC=CC=C1 OBXSGRKNCOCTTM-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 2
- 230000005978 brain dysfunction Effects 0.000 description 2
- 230000031709 bromination Effects 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 230000037410 cognitive enhancement Effects 0.000 description 2
- 239000002475 cognitive enhancer Substances 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
- NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 229910052805 deuterium Inorganic materials 0.000 description 2
- 206010012601 diabetes mellitus Diseases 0.000 description 2
- 229940043279 diisopropylamine Drugs 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 229960003530 donepezil Drugs 0.000 description 2
- 229960003638 dopamine Drugs 0.000 description 2
- 206010013663 drug dependence Diseases 0.000 description 2
- 239000003596 drug target Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000009977 dual effect Effects 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 230000002996 emotional effect Effects 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- DJQCWYZOWVCBEM-UHFFFAOYSA-N ethyl 1-benzyl-4h-pyrrolo[3,2-b]pyrrole-5-carboxylate Chemical compound C1=CC=2NC(C(=O)OCC)=CC=2N1CC1=CC=CC=C1 DJQCWYZOWVCBEM-UHFFFAOYSA-N 0.000 description 2
- RXJWDJMFTFKADU-UHFFFAOYSA-N ethyl 1-benzyl-6H-pyrrolo[2,3-c]pyrazole-5-carboxylate Chemical compound C1=2NC(C(=O)OCC)=CC=2C=NN1CC1=CC=CC=C1 RXJWDJMFTFKADU-UHFFFAOYSA-N 0.000 description 2
- CUTDJCLKKQWXGM-UHFFFAOYSA-N ethyl 1-benzylpyrazole-4-carboxylate Chemical compound C1=C(C(=O)OCC)C=NN1CC1=CC=CC=C1 CUTDJCLKKQWXGM-UHFFFAOYSA-N 0.000 description 2
- BJZSJXBOHBVOKH-UHFFFAOYSA-N ethyl 1-methyl-4h-pyrrolo[3,2-b]pyrrole-5-carboxylate Chemical compound CN1C=CC2=C1C=C(C(=O)OCC)N2 BJZSJXBOHBVOKH-UHFFFAOYSA-N 0.000 description 2
- BRRNEOTUICFFJO-UHFFFAOYSA-N ethyl 2-(2-phenylethyl)-4h-thieno[3,2-b]pyrrole-5-carboxylate Chemical compound C=1C=2NC(C(=O)OCC)=CC=2SC=1CCC1=CC=CC=C1 BRRNEOTUICFFJO-UHFFFAOYSA-N 0.000 description 2
- QLFZCCPLTLIWTK-UHFFFAOYSA-N ethyl 2-(4-chlorobenzoyl)-6h-thieno[2,3-b]pyrrole-5-carboxylate Chemical compound S1C=2NC(C(=O)OCC)=CC=2C=C1C(=O)C1=CC=C(Cl)C=C1 QLFZCCPLTLIWTK-UHFFFAOYSA-N 0.000 description 2
- SEXGWGJXHDQQDY-UHFFFAOYSA-N ethyl 2-azido-3-(4-benzylfuran-2-yl)prop-2-enoate Chemical compound O1C(C=C(C(=O)OCC)N=[N+]=[N-])=CC(CC=2C=CC=CC=2)=C1 SEXGWGJXHDQQDY-UHFFFAOYSA-N 0.000 description 2
- BVEQPQVAYIFRCK-UHFFFAOYSA-N ethyl 2-azido-3-(4-fluorothiophen-2-yl)prop-2-enoate Chemical compound CCOC(=O)C(N=[N+]=[N-])=CC1=CC(F)=CS1 BVEQPQVAYIFRCK-UHFFFAOYSA-N 0.000 description 2
- VDRZDKAEMRQURL-UHFFFAOYSA-N ethyl 2-azido-3-(5-benzylfuran-2-yl)prop-2-enoate Chemical compound O1C(C=C(C(=O)OCC)N=[N+]=[N-])=CC=C1CC1=CC=CC=C1 VDRZDKAEMRQURL-UHFFFAOYSA-N 0.000 description 2
- GMHVTKGBAZYUHW-UHFFFAOYSA-N ethyl 2-azido-3-(5-fluorofuran-2-yl)prop-2-enoate Chemical compound CCOC(=O)C(N=[N+]=[N-])=CC1=CC=C(F)O1 GMHVTKGBAZYUHW-UHFFFAOYSA-N 0.000 description 2
- XHELTWFUFRUTPH-UHFFFAOYSA-N ethyl 2-azido-3-(5-fluorothiophen-2-yl)prop-2-enoate Chemical compound CCOC(=O)C(N=[N+]=[N-])=CC1=CC=C(F)S1 XHELTWFUFRUTPH-UHFFFAOYSA-N 0.000 description 2
- DBYWTQSBIHSINZ-UHFFFAOYSA-N ethyl 2-azido-3-(5-methylthiophen-2-yl)prop-2-enoate Chemical compound CCOC(=O)C(N=[N+]=[N-])=CC1=CC=C(C)S1 DBYWTQSBIHSINZ-UHFFFAOYSA-N 0.000 description 2
- WNEKBYWOAQMLLY-UHFFFAOYSA-N ethyl 2-benzyl-4h-furo[3,2-b]pyrrole-5-carboxylate Chemical compound C=1C=2NC(C(=O)OCC)=CC=2OC=1CC1=CC=CC=C1 WNEKBYWOAQMLLY-UHFFFAOYSA-N 0.000 description 2
- KXGSKTSSCQBDOA-UHFFFAOYSA-N ethyl 2-bromo-4h-thieno[3,2-b]pyrrole-5-carboxylate Chemical compound S1C(Br)=CC2=C1C=C(C(=O)OCC)N2 KXGSKTSSCQBDOA-UHFFFAOYSA-N 0.000 description 2
- IXGBRRWUBAVAFD-UHFFFAOYSA-N ethyl 2-fluoro-4h-furo[3,2-b]pyrrole-5-carboxylate Chemical compound O1C(F)=CC2=C1C=C(C(=O)OCC)N2 IXGBRRWUBAVAFD-UHFFFAOYSA-N 0.000 description 2
- XZWXDDXLKJETRG-UHFFFAOYSA-N ethyl 2-fluoro-6h-thieno[2,3-b]pyrrole-5-carboxylate Chemical compound C1=C(F)SC2=C1C=C(C(=O)OCC)N2 XZWXDDXLKJETRG-UHFFFAOYSA-N 0.000 description 2
- OWWISVHKUJKEQH-UHFFFAOYSA-N ethyl 2-methyl-4h-thieno[3,2-b]pyrrole-5-carboxylate Chemical compound S1C(C)=CC2=C1C=C(C(=O)OCC)N2 OWWISVHKUJKEQH-UHFFFAOYSA-N 0.000 description 2
- OCAZMBQKNNYUBP-UHFFFAOYSA-N ethyl 3-(2-phenylethyl)-4h-furo[3,2-b]pyrrole-5-carboxylate Chemical compound C1=2NC(C(=O)OCC)=CC=2OC=C1CCC1=CC=CC=C1 OCAZMBQKNNYUBP-UHFFFAOYSA-N 0.000 description 2
- GUPVCCGLMZBFIR-UHFFFAOYSA-N ethyl 3-(2-phenylethyl)-4h-thieno[3,2-b]pyrrole-5-carboxylate Chemical compound C1=2NC(C(=O)OCC)=CC=2SC=C1CCC1=CC=CC=C1 GUPVCCGLMZBFIR-UHFFFAOYSA-N 0.000 description 2
- YMXHMJXEIUCOLH-UHFFFAOYSA-N ethyl 3-(2-tert-butylsilyloxypropan-2-yl)-4H-furo[3,2-b]pyrrole-5-carboxylate Chemical compound C(C)(C)(C)[SiH2]OC(C1=COC2=C1NC(=C2)C(=O)OCC)(C)C YMXHMJXEIUCOLH-UHFFFAOYSA-N 0.000 description 2
- UREYLMFRWAPIHQ-UHFFFAOYSA-N ethyl 3-benzyl-4h-furo[3,2-b]pyrrole-5-carboxylate Chemical compound C1=2NC(C(=O)OCC)=CC=2OC=C1CC1=CC=CC=C1 UREYLMFRWAPIHQ-UHFFFAOYSA-N 0.000 description 2
- OEMMLLJQDKJIPQ-UHFFFAOYSA-N ethyl 3-benzyl-6h-thieno[2,3-b]pyrrole-5-carboxylate Chemical compound C=1SC=2NC(C(=O)OCC)=CC=2C=1CC1=CC=CC=C1 OEMMLLJQDKJIPQ-UHFFFAOYSA-N 0.000 description 2
- BRCYQLJSKNOAFL-UHFFFAOYSA-N ethyl 3-bromo-4h-furo[3,2-b]pyrrole-5-carboxylate Chemical compound O1C=C(Br)C2=C1C=C(C(=O)OCC)N2 BRCYQLJSKNOAFL-UHFFFAOYSA-N 0.000 description 2
- LQGXFBUNQQNLKA-UHFFFAOYSA-N ethyl 3-bromo-6h-thieno[2,3-b]pyrrole-5-carboxylate Chemical compound BrC1=CSC2=C1C=C(C(=O)OCC)N2 LQGXFBUNQQNLKA-UHFFFAOYSA-N 0.000 description 2
- GMQBSQREBGIUFK-UHFFFAOYSA-N ethyl 3-chloro-4h-furo[3,2-b]pyrrole-5-carboxylate Chemical compound O1C=C(Cl)C2=C1C=C(C(=O)OCC)N2 GMQBSQREBGIUFK-UHFFFAOYSA-N 0.000 description 2
- WYFWXZCADUWGGH-UHFFFAOYSA-N ethyl 3-methyl-4h-furo[3,2-b]pyrrole-5-carboxylate Chemical compound O1C=C(C)C2=C1C=C(C(=O)OCC)N2 WYFWXZCADUWGGH-UHFFFAOYSA-N 0.000 description 2
- OQWHBCIKOUGKFT-UHFFFAOYSA-N ethyl 3-phenyl-6h-thieno[2,3-b]pyrrole-5-carboxylate Chemical compound C=1SC=2NC(C(=O)OCC)=CC=2C=1C1=CC=CC=C1 OQWHBCIKOUGKFT-UHFFFAOYSA-N 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 208000033699 familial Guillain-Barre syndrome Diseases 0.000 description 2
- 230000006390 fear memory Effects 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical class O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 229940093915 gynecological organic acid Drugs 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000004312 hexamethylene tetramine Substances 0.000 description 2
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- RCBVKBFIWMOMHF-UHFFFAOYSA-L hydroxy-(hydroxy(dioxo)chromio)oxy-dioxochromium;pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1.O[Cr](=O)(=O)O[Cr](O)(=O)=O RCBVKBFIWMOMHF-UHFFFAOYSA-L 0.000 description 2
- 208000013403 hyperactivity Diseases 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 150000002475 indoles Chemical class 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N isopropyl alcohol Natural products CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000001404 mediated effect Effects 0.000 description 2
- 230000009245 menopause Effects 0.000 description 2
- ASHPSTQAODFMLF-UHFFFAOYSA-N methyl 1-benzylpyrrole-2-carboxylate Chemical compound COC(=O)C1=CC=CN1CC1=CC=CC=C1 ASHPSTQAODFMLF-UHFFFAOYSA-N 0.000 description 2
- VDJYJSUDISVNRS-UHFFFAOYSA-N methyl 2-(trifluoromethoxy)benzoate Chemical compound COC(=O)C1=CC=CC=C1OC(F)(F)F VDJYJSUDISVNRS-UHFFFAOYSA-N 0.000 description 2
- MNKSOBXLSSJMIF-UHFFFAOYSA-N methyl 6-bromo-4h-furo[3,2-b]pyrrole-5-carboxylate Chemical compound C1=COC2=C1NC(C(=O)OC)=C2Br MNKSOBXLSSJMIF-UHFFFAOYSA-N 0.000 description 2
- QVQYZWXETCGKKZ-UHFFFAOYSA-N methyl 6-fluoro-4h-furo[3,2-b]pyrrole-5-carboxylate Chemical compound C1=COC2=C1NC(C(=O)OC)=C2F QVQYZWXETCGKKZ-UHFFFAOYSA-N 0.000 description 2
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 238000002156 mixing Methods 0.000 description 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 description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 201000006417 multiple sclerosis Diseases 0.000 description 2
- 210000003205 muscle Anatomy 0.000 description 2
- 230000007658 neurological function Effects 0.000 description 2
- 230000003040 nociceptive effect Effects 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 235000020824 obesity Nutrition 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 208000019906 panic disease Diseases 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 208000035824 paresthesia Diseases 0.000 description 2
- 208000033300 perinatal asphyxia Diseases 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000002953 phosphate buffered saline Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000000902 placebo Substances 0.000 description 2
- 229940068196 placebo Drugs 0.000 description 2
- 230000000069 prophylactic effect Effects 0.000 description 2
- 238000001671 psychotherapy Methods 0.000 description 2
- LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 238000012552 review Methods 0.000 description 2
- KIWUVOGUEXMXSV-UHFFFAOYSA-N rhodanine Chemical compound O=C1CSC(=S)N1 KIWUVOGUEXMXSV-UHFFFAOYSA-N 0.000 description 2
- 230000000698 schizophrenic effect Effects 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 230000009155 sensory pathway Effects 0.000 description 2
- 208000019116 sleep disease Diseases 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 235000009518 sodium iodide Nutrition 0.000 description 2
- 239000008247 solid mixture Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 210000000278 spinal cord Anatomy 0.000 description 2
- 210000001032 spinal nerve Anatomy 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- 150000003456 sulfonamides Chemical class 0.000 description 2
- HZTCVVJJSBKXMA-UHFFFAOYSA-N tert-butyl-[(3,3-difluoro-2h-furan-5-yl)methoxy]-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)OCC1=CC(F)(F)CO1 HZTCVVJJSBKXMA-UHFFFAOYSA-N 0.000 description 2
- ZUNINWFVODGKGI-UHFFFAOYSA-N tert-butyl-[(4-fluorofuran-2-yl)methoxy]-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)OCC1=CC(F)=CO1 ZUNINWFVODGKGI-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 125000005309 thioalkoxy group Chemical group 0.000 description 2
- 150000003568 thioethers Chemical class 0.000 description 2
- 238000012549 training Methods 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
- 238000006478 transmetalation reaction Methods 0.000 description 2
- 230000008733 trauma Effects 0.000 description 2
- 210000003901 trigeminal nerve Anatomy 0.000 description 2
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 2
- ONDSBJMLAHVLMI-UHFFFAOYSA-N trimethylsilyldiazomethane Chemical compound C[Si](C)(C)[CH-][N+]#N ONDSBJMLAHVLMI-UHFFFAOYSA-N 0.000 description 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 2
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 230000009385 viral infection Effects 0.000 description 2
- 230000003936 working memory Effects 0.000 description 2
- QCHFTSOMWOSFHM-WPRPVWTQSA-N (+)-Pilocarpine Chemical compound C1OC(=O)[C@@H](CC)[C@H]1CC1=CN=CN1C QCHFTSOMWOSFHM-WPRPVWTQSA-N 0.000 description 1
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- PXZNJHHUYJRFPZ-UHFFFAOYSA-N (4-bromothiophen-2-yl)methanol Chemical compound OCC1=CC(Br)=CS1 PXZNJHHUYJRFPZ-UHFFFAOYSA-N 0.000 description 1
- ABNTYKOJPTVOSK-UHFFFAOYSA-N (4-bromothiophen-2-yl)methoxy-tert-butyl-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(C(C)(C)C)OCC1=CC(Br)=CS1 ABNTYKOJPTVOSK-UHFFFAOYSA-N 0.000 description 1
- ANQLQOQLYYSYQP-UHFFFAOYSA-N (5-fluorothiophen-2-yl)methanol Chemical compound OCC1=CC=C(F)S1 ANQLQOQLYYSYQP-UHFFFAOYSA-N 0.000 description 1
- JUWYQISLQJRRNT-UHFFFAOYSA-N (5-formylfuran-2-yl)boronic acid Chemical compound OB(O)C1=CC=C(C=O)O1 JUWYQISLQJRRNT-UHFFFAOYSA-N 0.000 description 1
- WKKQLNQKSANODS-UHFFFAOYSA-N (5-formylfuran-3-yl)methyl benzoate Chemical compound O1C(C=O)=CC(COC(=O)C=2C=CC=CC=2)=C1 WKKQLNQKSANODS-UHFFFAOYSA-N 0.000 description 1
- DEQOVKFWRPOPQP-UHFFFAOYSA-N (5-formylthiophen-2-yl)boronic acid Chemical compound OB(O)C1=CC=C(C=O)S1 DEQOVKFWRPOPQP-UHFFFAOYSA-N 0.000 description 1
- ZCUFJAORCNFWOF-UHFFFAOYSA-N (5-formylthiophen-3-yl)boronic acid Chemical compound OB(O)C1=CSC(C=O)=C1 ZCUFJAORCNFWOF-UHFFFAOYSA-N 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 1
- PYHRZPFZZDCOPH-QXGOIDDHSA-N (S)-amphetamine sulfate Chemical compound [H+].[H+].[O-]S([O-])(=O)=O.C[C@H](N)CC1=CC=CC=C1.C[C@H](N)CC1=CC=CC=C1 PYHRZPFZZDCOPH-QXGOIDDHSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 125000000196 1,4-pentadienyl group Chemical group [H]C([*])=C([H])C([H])([H])C([H])=C([H])[H] 0.000 description 1
- MDAOZTFXAXKOTE-UHFFFAOYSA-N 1,5-dihydropyrrolo[3,4-b]pyrrole Chemical class N1C=C2NC=CC2=C1 MDAOZTFXAXKOTE-UHFFFAOYSA-N 0.000 description 1
- VWDXBYMJWCBQHM-UHFFFAOYSA-N 1,5-dihydropyrrolo[3,4-b]pyrrole-2-carboxylic acid Chemical class N1C=C2NC(C(=O)O)=CC2=C1 VWDXBYMJWCBQHM-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 1
- DOHJTIXLBCEKQC-UHFFFAOYSA-N 1h-furo[3,4-b]pyrrole-2-carboxylic acid Chemical class O1C=C2NC(C(=O)O)=CC2=C1 DOHJTIXLBCEKQC-UHFFFAOYSA-N 0.000 description 1
- LRGBDJBDJXZTTD-UHFFFAOYSA-N 1h-pyrazole-4-carbaldehyde Chemical compound O=CC=1C=NNC=1 LRGBDJBDJXZTTD-UHFFFAOYSA-N 0.000 description 1
- ICFGFAUMBISMLR-UHFFFAOYSA-N 1h-pyrazole-5-carbaldehyde Chemical compound O=CC=1C=CNN=1 ICFGFAUMBISMLR-UHFFFAOYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- JFGOCNAOOLXIMV-UHFFFAOYSA-N 2,3-dichloro-4h-thieno[3,2-b]pyrrole-5-carboxylic acid Chemical compound S1C(Cl)=C(Cl)C2=C1C=C(C(=O)O)N2 JFGOCNAOOLXIMV-UHFFFAOYSA-N 0.000 description 1
- UQABPUYRHQRGLU-UHFFFAOYSA-N 2,3-dichloro-6h-thieno[2,3-b]pyrrole-5-carboxylic acid Chemical compound ClC1=C(Cl)SC2=C1C=C(C(=O)O)N2 UQABPUYRHQRGLU-UHFFFAOYSA-N 0.000 description 1
- RQWCPZNVQXZQIG-UHFFFAOYSA-N 2,4-dichloro-6h-thieno[2,3-b]pyrrole-5-carboxylic acid Chemical compound S1C(Cl)=CC2=C1NC(C(=O)O)=C2Cl RQWCPZNVQXZQIG-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- HWSDRAPTZRYXHN-UHFFFAOYSA-N 2-(4-chlorophenyl)ethenylboronic acid Chemical compound OB(O)C=CC1=CC=C(Cl)C=C1 HWSDRAPTZRYXHN-UHFFFAOYSA-N 0.000 description 1
- BPXKZEMBEZGUAH-UHFFFAOYSA-N 2-(chloromethoxy)ethyl-trimethylsilane Chemical compound C[Si](C)(C)CCOCCl BPXKZEMBEZGUAH-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 description 1
- LILXDMFJXYAKMK-UHFFFAOYSA-N 2-bromo-1,1-diethoxyethane Chemical compound CCOC(CBr)OCC LILXDMFJXYAKMK-UHFFFAOYSA-N 0.000 description 1
- IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 description 1
- OVXJWSYBABKZMD-UHFFFAOYSA-N 2-chloro-1,1-diethoxyethane Chemical compound CCOC(CCl)OCC OVXJWSYBABKZMD-UHFFFAOYSA-N 0.000 description 1
- SOGNHUJSAKAIRG-UHFFFAOYSA-N 2-chloro-6h-thieno[2,3-b]pyrrole-5-carboxylic acid Chemical compound C1=C(Cl)SC2=C1C=C(C(=O)O)N2 SOGNHUJSAKAIRG-UHFFFAOYSA-N 0.000 description 1
- PAUZWINNRRQSPP-UHFFFAOYSA-N 2-cyano-4h-thieno[3,2-b]pyrrole-5-carboxylic acid Chemical compound S1C(C#N)=CC2=C1C=C(C(=O)O)N2 PAUZWINNRRQSPP-UHFFFAOYSA-N 0.000 description 1
- FZOKMMKREHLHBP-UHFFFAOYSA-N 2-fluoro-4-(2-trimethylsilylethoxymethyl)thieno[3,2-b]pyrrole-5-carboxylic acid Chemical compound S1C(F)=CC2=C1C=C(C(O)=O)N2COCC[Si](C)(C)C FZOKMMKREHLHBP-UHFFFAOYSA-N 0.000 description 1
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- JYUOZYKKKGDMKH-UHFFFAOYSA-N 2-methyl-4-(trifluoromethyl)furan Chemical compound CC1=CC(C(F)(F)F)=CO1 JYUOZYKKKGDMKH-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=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
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- OXDSTEQMQRCOGK-UHFFFAOYSA-N 3-fluorothiophene-2-carbaldehyde Chemical compound FC=1C=CSC=1C=O OXDSTEQMQRCOGK-UHFFFAOYSA-N 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- BNYIQEFWGSXIKQ-UHFFFAOYSA-N 3-methylfuran-2-carboxylic acid Chemical compound CC=1C=COC=1C(O)=O BNYIQEFWGSXIKQ-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
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- XBXZTENDDALBBV-UHFFFAOYSA-N 4,4-difluoropent-2-yne-1,5-diol Chemical compound OCC#CC(F)(F)CO XBXZTENDDALBBV-UHFFFAOYSA-N 0.000 description 1
- CHRAVDVWAPGZOY-UHFFFAOYSA-N 4,5-dibromothiophene-2-carbaldehyde Chemical compound BrC=1C=C(C=O)SC=1Br CHRAVDVWAPGZOY-UHFFFAOYSA-N 0.000 description 1
- YHEMDDZDHYKQGZ-UHFFFAOYSA-N 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-carbaldehyde Chemical compound O1C(C)(C)C(C)(C)OB1C1=COC(C=O)=C1 YHEMDDZDHYKQGZ-UHFFFAOYSA-N 0.000 description 1
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 1
- AXCTUMLEPJKRIX-IHWYPQMZSA-N 4-[(z)-prop-1-enyl]furan-2-carbaldehyde Chemical compound C\C=C/C1=COC(C=O)=C1 AXCTUMLEPJKRIX-IHWYPQMZSA-N 0.000 description 1
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 1
- MBVFRSJFKMJRHA-UHFFFAOYSA-N 4-fluoro-1-benzofuran-7-carbaldehyde Chemical compound FC1=CC=C(C=O)C2=C1C=CO2 MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 description 1
- QSXQHBKWSNXBEZ-UHFFFAOYSA-N 4-fluorothiophene-3-carbaldehyde Chemical compound FC1=CSC=C1C=O QSXQHBKWSNXBEZ-UHFFFAOYSA-N 0.000 description 1
- HVXCGIPRXBJIRK-UHFFFAOYSA-N 4-methylthiophene-2-carbaldehyde Chemical compound CC1=CSC(C=O)=C1 HVXCGIPRXBJIRK-UHFFFAOYSA-N 0.000 description 1
- STJZAPSUEPQINW-UHFFFAOYSA-N 4-o-tert-butyl 5-o-methyl furo[3,2-b]pyrrole-4,5-dicarboxylate Chemical compound O1C=CC2=C1C=C(C(=O)OC)N2C(=O)OC(C)(C)C STJZAPSUEPQINW-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
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 description 1
- YFMUACLZRVJOBK-UHFFFAOYSA-N 5-(2-phenylethynyl)thiophene-2-carbaldehyde Chemical compound S1C(C=O)=CC=C1C#CC1=CC=CC=C1 YFMUACLZRVJOBK-UHFFFAOYSA-N 0.000 description 1
- KLVCIHFXPHKSPD-UHFFFAOYSA-N 5-(trifluoromethyl)furan-2-carbaldehyde Chemical compound FC(F)(F)C1=CC=C(C=O)O1 KLVCIHFXPHKSPD-UHFFFAOYSA-N 0.000 description 1
- VAUMDUIUEPIGHM-UHFFFAOYSA-N 5-Methyl-2-thiophenecarboxaldehyde Chemical compound CC1=CC=C(C=O)S1 VAUMDUIUEPIGHM-UHFFFAOYSA-N 0.000 description 1
- GFBVUFQNHLUCPX-UHFFFAOYSA-N 5-bromothiophene-2-carbaldehyde Chemical compound BrC1=CC=C(C=O)S1 GFBVUFQNHLUCPX-UHFFFAOYSA-N 0.000 description 1
- VWYFITBWBRVBSW-UHFFFAOYSA-N 5-chlorothiophene-2-carbaldehyde Chemical compound ClC1=CC=C(C=O)S1 VWYFITBWBRVBSW-UHFFFAOYSA-N 0.000 description 1
- SHNRXUWGUKDPMA-UHFFFAOYSA-N 5-formyl-2-furoic acid Chemical compound OC(=O)C1=CC=C(C=O)O1 SHNRXUWGUKDPMA-UHFFFAOYSA-N 0.000 description 1
- 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 description 1
- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 description 1
- SEWHHLSEXYDKMQ-UHFFFAOYSA-N 5-iodothiophene-3-carbaldehyde Chemical compound IC1=CC(C=O)=CS1 SEWHHLSEXYDKMQ-UHFFFAOYSA-N 0.000 description 1
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 description 1
- GELCPPPIKQQUEJ-UHFFFAOYSA-N 6-fluoro-4-(2-trimethylsilylethoxymethyl)thieno[3,2-b]pyrrole-5-carboxylic acid Chemical compound S1C=CC2=C1C(F)=C(C(O)=O)N2COCC[Si](C)(C)C GELCPPPIKQQUEJ-UHFFFAOYSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- 229930000680 A04AD01 - Scopolamine Natural products 0.000 description 1
- 206010000087 Abdominal pain upper Diseases 0.000 description 1
- 206010001497 Agitation Diseases 0.000 description 1
- 101710134784 Agnoprotein Proteins 0.000 description 1
- 208000007848 Alcoholism Diseases 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 208000000103 Anorexia Nervosa Diseases 0.000 description 1
- 206010002652 Anorgasmia Diseases 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- 208000006820 Arthralgia Diseases 0.000 description 1
- 208000036487 Arthropathies Diseases 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 206010006002 Bone pain Diseases 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 101800004538 Bradykinin Proteins 0.000 description 1
- 201000006474 Brain Ischemia Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 208000032841 Bulimia Diseases 0.000 description 1
- 206010006550 Bulimia nervosa Diseases 0.000 description 1
- PUOZPEBSERMLTQ-UHFFFAOYSA-N C1=COC2=C1NC(C(=O)O)=C2I Chemical compound C1=COC2=C1NC(C(=O)O)=C2I PUOZPEBSERMLTQ-UHFFFAOYSA-N 0.000 description 1
- VGJSQNCLVSEWCU-UHFFFAOYSA-N CN(C)CC1=C(NC2=C1SC=C2)C(=O)O Chemical compound CN(C)CC1=C(NC2=C1SC=C2)C(=O)O VGJSQNCLVSEWCU-UHFFFAOYSA-N 0.000 description 1
- 206010006895 Cachexia Diseases 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-NJFSPNSNSA-N Carbon-14 Chemical compound [14C] OKTJSMMVPCPJKN-NJFSPNSNSA-N 0.000 description 1
- 208000002177 Cataract Diseases 0.000 description 1
- 206010064012 Central pain syndrome Diseases 0.000 description 1
- 206010008120 Cerebral ischaemia Diseases 0.000 description 1
- 206010008479 Chest Pain Diseases 0.000 description 1
- 206010008874 Chronic Fatigue Syndrome Diseases 0.000 description 1
- 206010057645 Chronic Inflammatory Demyelinating Polyradiculoneuropathy Diseases 0.000 description 1
- 208000030939 Chronic inflammatory demyelinating polyneuropathy Diseases 0.000 description 1
- 206010010071 Coma Diseases 0.000 description 1
- 206010010144 Completed suicide Diseases 0.000 description 1
- 206010057254 Connective tissue inflammation Diseases 0.000 description 1
- 208000034656 Contusions Diseases 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 150000008574 D-amino acids Chemical class 0.000 description 1
- 206010012335 Dependence 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
- 208000007342 Diabetic Nephropathies Diseases 0.000 description 1
- 206010012689 Diabetic retinopathy Diseases 0.000 description 1
- 206010013886 Dysaesthesia Diseases 0.000 description 1
- 208000012661 Dyskinesia Diseases 0.000 description 1
- 206010014498 Embolic stroke Diseases 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 208000033962 Fontaine progeroid syndrome Diseases 0.000 description 1
- 102000005915 GABA Receptors Human genes 0.000 description 1
- 108010005551 GABA Receptors Proteins 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 102000018899 Glutamate Receptors Human genes 0.000 description 1
- 108010027915 Glutamate Receptors Proteins 0.000 description 1
- 102000007390 Glycogen Phosphorylase Human genes 0.000 description 1
- 108010046163 Glycogen Phosphorylase Proteins 0.000 description 1
- QXZGBUJJYSLZLT-UHFFFAOYSA-N H-Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg-OH Natural products NC(N)=NCCCC(N)C(=O)N1CCCC1C(=O)N1C(C(=O)NCC(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CO)C(=O)N2C(CCC2)C(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CCCN=C(N)N)C(O)=O)CCC1 QXZGBUJJYSLZLT-UHFFFAOYSA-N 0.000 description 1
- 208000016988 Hemorrhagic Stroke Diseases 0.000 description 1
- 208000007514 Herpes zoster Diseases 0.000 description 1
- 241001559542 Hippocampus hippocampus Species 0.000 description 1
- 101000605127 Homo sapiens Prostaglandin G/H synthase 2 Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- STECJAGHUSJQJN-GAUPFVANSA-N Hyoscine Natural products C1([C@H](CO)C(=O)OC2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-GAUPFVANSA-N 0.000 description 1
- 208000035150 Hypercholesterolemia Diseases 0.000 description 1
- 206010051161 Hyperglucagonaemia Diseases 0.000 description 1
- 206010060378 Hyperinsulinaemia Diseases 0.000 description 1
- 208000031226 Hyperlipidaemia Diseases 0.000 description 1
- 206010065952 Hyperpathia Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 208000004044 Hypesthesia Diseases 0.000 description 1
- 208000013016 Hypoglycemia Diseases 0.000 description 1
- 206010022489 Insulin Resistance Diseases 0.000 description 1
- 208000005168 Intussusception Diseases 0.000 description 1
- 208000012659 Joint disease Diseases 0.000 description 1
- YQEZLKZALYSWHR-UHFFFAOYSA-N Ketamine Chemical compound C=1C=CC=C(Cl)C=1C1(NC)CCCCC1=O YQEZLKZALYSWHR-UHFFFAOYSA-N 0.000 description 1
- 102100035792 Kininogen-1 Human genes 0.000 description 1
- 238000006000 Knoevenagel condensation reaction Methods 0.000 description 1
- 229930195714 L-glutamate Natural products 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
- 208000008930 Low Back Pain Diseases 0.000 description 1
- 229910052765 Lutetium Inorganic materials 0.000 description 1
- 206010026749 Mania Diseases 0.000 description 1
- 208000021964 McLeod neuroacanthocytosis syndrome Diseases 0.000 description 1
- 208000026486 McLeod syndrome Diseases 0.000 description 1
- DUGOZIWVEXMGBE-UHFFFAOYSA-N Methylphenidate Chemical compound C=1C=CC=CC=1C(C(=O)OC)C1CCCCN1 DUGOZIWVEXMGBE-UHFFFAOYSA-N 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 208000016285 Movement disease Diseases 0.000 description 1
- 101100189356 Mus musculus Papolb gene Proteins 0.000 description 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
- STECJAGHUSJQJN-UHFFFAOYSA-N N-Methyl-scopolamin Natural products C1C(C2C3O2)N(C)C3CC1OC(=O)C(CO)C1=CC=CC=C1 STECJAGHUSJQJN-UHFFFAOYSA-N 0.000 description 1
- 206010028836 Neck pain Diseases 0.000 description 1
- 206010029174 Nerve compression Diseases 0.000 description 1
- 208000031264 Nerve root compression Diseases 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 208000001294 Nociceptive Pain Diseases 0.000 description 1
- 229910003849 O-Si Inorganic materials 0.000 description 1
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 description 1
- 102000004316 Oxidoreductases Human genes 0.000 description 1
- 108090000854 Oxidoreductases Proteins 0.000 description 1
- 229910003872 O—Si Inorganic materials 0.000 description 1
- 206010033799 Paralysis Diseases 0.000 description 1
- 101150003085 Pdcl gene Proteins 0.000 description 1
- PIJVFDBKTWXHHD-UHFFFAOYSA-N Physostigmine Natural products C12=CC(OC(=O)NC)=CC=C2N(C)C2C1(C)CCN2C PIJVFDBKTWXHHD-UHFFFAOYSA-N 0.000 description 1
- GMZVRMREEHBGGF-UHFFFAOYSA-N Piracetam Chemical compound NC(=O)CN1CCCC1=O GMZVRMREEHBGGF-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 206010036618 Premenstrual syndrome Diseases 0.000 description 1
- 102000003946 Prolactin Human genes 0.000 description 1
- 108010057464 Prolactin Proteins 0.000 description 1
- 102000002067 Protein Subunits Human genes 0.000 description 1
- 108010001267 Protein Subunits Proteins 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- QCHFTSOMWOSFHM-UHFFFAOYSA-N SJ000285536 Natural products C1OC(=O)C(CC)C1CC1=CN=CN1C QCHFTSOMWOSFHM-UHFFFAOYSA-N 0.000 description 1
- 206010039966 Senile dementia Diseases 0.000 description 1
- 201000001880 Sexual dysfunction Diseases 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 1
- 206010041250 Social phobia Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 206010043118 Tardive Dyskinesia Diseases 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 208000031674 Traumatic Acute Stress disease Diseases 0.000 description 1
- 208000030886 Traumatic Brain injury Diseases 0.000 description 1
- 206010044565 Tremor Diseases 0.000 description 1
- 206010044688 Trisomy 21 Diseases 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- 206010064390 Tumour invasion Diseases 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 208000021017 Weight Gain Diseases 0.000 description 1
- 206010052428 Wound Diseases 0.000 description 1
- CBMCZKMIOZYAHS-IHWYPQMZSA-N [(z)-prop-1-enyl]boronic acid Chemical compound C\C=C/B(O)O CBMCZKMIOZYAHS-IHWYPQMZSA-N 0.000 description 1
- PNDPGZBMCMUPRI-XXSWNUTMSA-N [125I][125I] Chemical compound [125I][125I] PNDPGZBMCMUPRI-XXSWNUTMSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 208000027093 acute inflammatory demyelinating polyradiculoneuropathy Diseases 0.000 description 1
- 208000026345 acute stress disease Diseases 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 238000012382 advanced drug delivery Methods 0.000 description 1
- 230000007000 age related cognitive decline Effects 0.000 description 1
- 201000007930 alcohol dependence Diseases 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- IAJILQKETJEXLJ-RSJOWCBRSA-N aldehydo-D-galacturonic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-RSJOWCBRSA-N 0.000 description 1
- IAJILQKETJEXLJ-QTBDOELSSA-N aldehydo-D-glucuronic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-QTBDOELSSA-N 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 125000005237 alkyleneamino group Chemical group 0.000 description 1
- 125000005238 alkylenediamino group Chemical group 0.000 description 1
- 125000005530 alkylenedioxy group Chemical group 0.000 description 1
- 125000005529 alkyleneoxy group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- VLSMHEGGTFMBBZ-UHFFFAOYSA-N alpha-Kainic acid Natural products CC(=C)C1CNC(C(O)=O)C1CC(O)=O VLSMHEGGTFMBBZ-UHFFFAOYSA-N 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229940025084 amphetamine Drugs 0.000 description 1
- 210000004727 amygdala Anatomy 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 229960000793 aniracetam Drugs 0.000 description 1
- ZXNRTKGTQJPIJK-UHFFFAOYSA-N aniracetam Chemical compound C1=CC(OC)=CC=C1C(=O)N1C(=O)CCC1 ZXNRTKGTQJPIJK-UHFFFAOYSA-N 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000003502 anti-nociceptive effect Effects 0.000 description 1
- 230000000561 anti-psychotic effect Effects 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000019789 appetite Nutrition 0.000 description 1
- 230000036528 appetite Effects 0.000 description 1
- 230000009118 appropriate response Effects 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 125000005165 aryl thioxy group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 1
- 238000012093 association test Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000003693 atypical antipsychotic agent Substances 0.000 description 1
- 229940127236 atypical antipsychotics Drugs 0.000 description 1
- 230000002567 autonomic effect Effects 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 239000000022 bacteriostatic agent Substances 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 150000008316 benzisoxazoles Chemical class 0.000 description 1
- WXNOJTUTEXAZLD-UHFFFAOYSA-L benzonitrile;dichloropalladium Chemical compound Cl[Pd]Cl.N#CC1=CC=CC=C1.N#CC1=CC=CC=C1 WXNOJTUTEXAZLD-UHFFFAOYSA-L 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- YTFJQDNGSQJFNA-UHFFFAOYSA-L benzyl phosphate Chemical compound [O-]P([O-])(=O)OCC1=CC=CC=C1 YTFJQDNGSQJFNA-UHFFFAOYSA-L 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 238000002306 biochemical method Methods 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 230000008499 blood brain barrier function Effects 0.000 description 1
- 230000036765 blood level Effects 0.000 description 1
- 210000001218 blood-brain barrier Anatomy 0.000 description 1
- 230000037237 body shape Effects 0.000 description 1
- QXZGBUJJYSLZLT-FDISYFBBSA-N bradykinin Chemical compound NC(=N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1[C@H](C(=O)NCC(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CO)C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)CCC1 QXZGBUJJYSLZLT-FDISYFBBSA-N 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 230000009400 cancer invasion Effects 0.000 description 1
- 239000007894 caplet Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 230000003915 cell function Effects 0.000 description 1
- 230000006727 cell loss Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- 239000012069 chiral reagent Substances 0.000 description 1
- 230000000718 cholinopositive effect Effects 0.000 description 1
- QZHPTGXQGDFGEN-UHFFFAOYSA-N chromene Chemical compound C1=CC=C2C=C[CH]OC2=C1 QZHPTGXQGDFGEN-UHFFFAOYSA-N 0.000 description 1
- 208000037976 chronic inflammation Diseases 0.000 description 1
- 208000037893 chronic inflammatory disorder Diseases 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 230000003930 cognitive ability Effects 0.000 description 1
- 238000009225 cognitive behavioral therapy Methods 0.000 description 1
- 230000037411 cognitive enhancing Effects 0.000 description 1
- 230000036992 cognitive tasks Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 208000030251 communication disease Diseases 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 1
- 239000007891 compressed tablet Substances 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 230000009519 contusion Effects 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 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 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- WLVKDFJTYKELLQ-UHFFFAOYSA-N cyclopropylboronic acid Chemical compound OB(O)C1CC1 WLVKDFJTYKELLQ-UHFFFAOYSA-N 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- 230000005595 deprotonation Effects 0.000 description 1
- 238000010537 deprotonation reaction Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 229940119751 dextroamphetamine sulfate Drugs 0.000 description 1
- 208000033679 diabetic kidney disease Diseases 0.000 description 1
- JAEHVOBOWZVTFO-UHFFFAOYSA-N diazonio-[3-ethoxy-1-(4-fluorofuran-2-yl)-3-oxoprop-1-en-2-yl]azanide Chemical compound CCOC(=O)C(N=[N+]=[N-])=CC1=CC(F)=CO1 JAEHVOBOWZVTFO-UHFFFAOYSA-N 0.000 description 1
- RUCCAFSTHZZMHX-UHFFFAOYSA-N diazonio-[3-ethoxy-1-[4-(hydroxymethyl)furan-2-yl]-3-oxoprop-1-en-2-yl]azanide Chemical compound CCOC(=O)C(N=[N+]=[N-])=CC1=CC(CO)=CO1 RUCCAFSTHZZMHX-UHFFFAOYSA-N 0.000 description 1
- JQKJEPJLCSCBGW-UHFFFAOYSA-N dibutoxy(ethenyl)borane Chemical compound CCCCOB(C=C)OCCCC JQKJEPJLCSCBGW-UHFFFAOYSA-N 0.000 description 1
- WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- UCQFCFPECQILOL-UHFFFAOYSA-N diethyl hydrogen phosphate Chemical compound CCOP(O)(=O)OCC UCQFCFPECQILOL-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 230000006806 disease prevention Effects 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 208000035548 disruptive behavior disease Diseases 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- QLTXKCWMEZIHBJ-PJGJYSAQSA-N dizocilpine maleate Chemical compound OC(=O)\C=C/C(O)=O.C12=CC=CC=C2[C@]2(C)C3=CC=CC=C3C[C@H]1N2 QLTXKCWMEZIHBJ-PJGJYSAQSA-N 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 235000006694 eating habits Nutrition 0.000 description 1
- 239000006274 endogenous ligand Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 239000002532 enzyme inhibitor Substances 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- BJACDGFOTRXWLR-UHFFFAOYSA-N ethyl 1-(1-phenylethyl)-6H-pyrrolo[2,3-c]pyrazole-5-carboxylate Chemical compound C1=2NC(C(=O)OCC)=CC=2C=NN1C(C)C1=CC=CC=C1 BJACDGFOTRXWLR-UHFFFAOYSA-N 0.000 description 1
- KACZQOKEFKFNDB-UHFFFAOYSA-N ethyl 1h-pyrazole-4-carboxylate Chemical compound CCOC(=O)C=1C=NNC=1 KACZQOKEFKFNDB-UHFFFAOYSA-N 0.000 description 1
- CEOZSWLHUWRAHZ-UHFFFAOYSA-N ethyl 2-azido-3-[4-(2-phenylethyl)furan-2-yl]prop-2-enoate Chemical compound O1C(C=C(C(=O)OCC)N=[N+]=[N-])=CC(CCC=2C=CC=CC=2)=C1 CEOZSWLHUWRAHZ-UHFFFAOYSA-N 0.000 description 1
- CPLDTCZGUSCXFY-UHFFFAOYSA-N ethyl 2-azido-3-[4-[2-(4-chlorophenyl)ethyl]thiophen-3-yl]prop-2-enoate Chemical compound CCOC(=O)C(N=[N+]=[N-])=CC1=CSC=C1CCC1=CC=C(Cl)C=C1 CPLDTCZGUSCXFY-UHFFFAOYSA-N 0.000 description 1
- HVJJYOAPXBPQQV-UHFFFAOYSA-N ethyl 2-azidoacetate Chemical compound CCOC(=O)CN=[N+]=[N-] HVJJYOAPXBPQQV-UHFFFAOYSA-N 0.000 description 1
- HDQJHQCDPZOMJA-UHFFFAOYSA-N ethyl 3-(hydroxymethyl)-4h-furo[3,2-b]pyrrole-5-carboxylate Chemical compound O1C=C(CO)C2=C1C=C(C(=O)OCC)N2 HDQJHQCDPZOMJA-UHFFFAOYSA-N 0.000 description 1
- OQYHOTLOKXSWKL-HYXAFXHYSA-N ethyl 3-[(z)-prop-1-enyl]-4h-furo[3,2-b]pyrrole-5-carboxylate Chemical compound O1C=C(\C=C/C)C2=C1C=C(C(=O)OCC)N2 OQYHOTLOKXSWKL-HYXAFXHYSA-N 0.000 description 1
- BZCFLVAMRFKPBH-UHFFFAOYSA-N ethyl 3-ethyl-2-fluoro-4h-furo[3,2-b]pyrrole-5-carboxylate Chemical compound O1C(F)=C(CC)C2=C1C=C(C(=O)OCC)N2 BZCFLVAMRFKPBH-UHFFFAOYSA-N 0.000 description 1
- XQWPLXGMFLEVMU-UHFFFAOYSA-N ethyl 3-fluoro-4h-furo[3,2-b]pyrrole-5-carboxylate Chemical compound O1C=C(F)C2=C1C=C(C(=O)OCC)N2 XQWPLXGMFLEVMU-UHFFFAOYSA-N 0.000 description 1
- NRGDCPHIUQSYOH-UHFFFAOYSA-N ethyl 3-formyl-4h-furo[3,2-b]pyrrole-5-carboxylate Chemical compound O1C=C(C=O)C2=C1C=C(C(=O)OCC)N2 NRGDCPHIUQSYOH-UHFFFAOYSA-N 0.000 description 1
- MHYCRLGKOZWVEF-UHFFFAOYSA-N ethyl acetate;hydrate Chemical compound O.CCOC(C)=O MHYCRLGKOZWVEF-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 230000002964 excitative effect Effects 0.000 description 1
- 230000002461 excitatory amino acid Effects 0.000 description 1
- 239000003257 excitatory amino acid Substances 0.000 description 1
- 230000010326 executive functioning Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000008921 facial expression Effects 0.000 description 1
- 206010016256 fatigue Diseases 0.000 description 1
- 230000014061 fear response Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 210000001061 forehead Anatomy 0.000 description 1
- 230000022244 formylation Effects 0.000 description 1
- 238000006170 formylation reaction Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical class NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 208000037870 generalized anxiety Diseases 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
- 230000006589 gland dysfunction Effects 0.000 description 1
- 229940097043 glucuronic acid Drugs 0.000 description 1
- 150000002306 glutamic acid derivatives Chemical class 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000003979 granulating agent Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 210000003128 head Anatomy 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 125000004366 heterocycloalkenyl group Chemical group 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- 230000000971 hippocampal effect Effects 0.000 description 1
- 210000001320 hippocampus Anatomy 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- ZUFVXZVXEJHHBN-UHFFFAOYSA-N hydron;1,2,3,4-tetrahydroacridin-9-amine;chloride Chemical compound [Cl-].C1=CC=C2C([NH3+])=C(CCCC3)C3=NC2=C1 ZUFVXZVXEJHHBN-UHFFFAOYSA-N 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 201000001421 hyperglycemia Diseases 0.000 description 1
- 230000035879 hyperinsulinaemia Effects 0.000 description 1
- 208000006575 hypertriglyceridemia Diseases 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 208000034783 hypoesthesia Diseases 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 208000026278 immune system disease Diseases 0.000 description 1
- 238000005462 in vivo assay Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 230000000266 injurious effect Effects 0.000 description 1
- 206010022437 insomnia Diseases 0.000 description 1
- 208000020658 intracerebral hemorrhage Diseases 0.000 description 1
- 208000001286 intracranial vasospasm Diseases 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 230000009545 invasion Effects 0.000 description 1
- 230000026045 iodination Effects 0.000 description 1
- 238000006192 iodination reaction Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229940044173 iodine-125 Drugs 0.000 description 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
- 230000003447 ipsilateral effect Effects 0.000 description 1
- 230000002427 irreversible effect Effects 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
- 238000002955 isolation Methods 0.000 description 1
- ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- VLSMHEGGTFMBBZ-OOZYFLPDSA-N kainic acid Chemical compound CC(=C)[C@H]1CN[C@H](C(O)=O)[C@H]1CC(O)=O VLSMHEGGTFMBBZ-OOZYFLPDSA-N 0.000 description 1
- 229950006874 kainic acid Drugs 0.000 description 1
- 229960003299 ketamine Drugs 0.000 description 1
- 150000004715 keto acids Chemical class 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 230000003907 kidney function Effects 0.000 description 1
- 230000001535 kindling effect Effects 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 210000000088 lip Anatomy 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 230000003908 liver function Effects 0.000 description 1
- 230000006742 locomotor activity Effects 0.000 description 1
- 230000007787 long-term memory Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 159000000003 magnesium salts Chemical class 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
- 239000011976 maleic acid Substances 0.000 description 1
- 210000005171 mammalian brain Anatomy 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 230000005056 memory consolidation Effects 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 1
- GABXQZVOQAYXAG-UHFFFAOYSA-N methyl 2-[(dimethylamino)methyl]-4h-furo[3,2-b]pyrrole-5-carboxylate Chemical compound O1C(CN(C)C)=CC2=C1C=C(C(=O)OC)N2 GABXQZVOQAYXAG-UHFFFAOYSA-N 0.000 description 1
- SBBZXGMGOKVVOB-UHFFFAOYSA-N methyl 4h-thieno[3,2-b]pyrrole-5-carboxylate Chemical compound S1C=CC2=C1C=C(C(=O)OC)N2 SBBZXGMGOKVVOB-UHFFFAOYSA-N 0.000 description 1
- RJZIYUWKRUYUFL-UHFFFAOYSA-N methyl 6-[(dimethylamino)methyl]-4h-thieno[3,2-b]pyrrole-5-carboxylate Chemical compound C1=CSC2=C1NC(C(=O)OC)=C2CN(C)C RJZIYUWKRUYUFL-UHFFFAOYSA-N 0.000 description 1
- LNWIUIFDUWVWGQ-UHFFFAOYSA-N methyl 6-iodo-4h-furo[3,2-b]pyrrole-5-carboxylate Chemical compound C1=COC2=C1NC(C(=O)OC)=C2I LNWIUIFDUWVWGQ-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 229960001344 methylphenidate Drugs 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000007932 molded tablet Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 125000006682 monohaloalkyl group Chemical group 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 description 1
- 239000000472 muscarinic agonist Substances 0.000 description 1
- 230000004118 muscle contraction Effects 0.000 description 1
- 208000013465 muscle pain Diseases 0.000 description 1
- 230000036640 muscle relaxation Effects 0.000 description 1
- 230000017311 musculoskeletal movement, spinal reflex action Effects 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 210000004126 nerve fiber Anatomy 0.000 description 1
- 210000004498 neuroglial cell Anatomy 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 230000003955 neuronal function Effects 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- 239000002664 nootropic agent Substances 0.000 description 1
- 230000001777 nootropic effect Effects 0.000 description 1
- 210000001331 nose Anatomy 0.000 description 1
- 230000001473 noxious effect Effects 0.000 description 1
- 238000012587 nuclear overhauser effect experiment Methods 0.000 description 1
- 231100000862 numbness Toxicity 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 239000004533 oil dispersion Substances 0.000 description 1
- 229940005483 opioid analgesics Drugs 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229960001227 oxiracetam Drugs 0.000 description 1
- IHLAQQPQKRMGSS-UHFFFAOYSA-N oxiracetam Chemical compound NC(=O)CN1CC(O)CC1=O IHLAQQPQKRMGSS-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000004031 partial agonist Substances 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 235000014594 pastries Nutrition 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000008289 pathophysiological mechanism Effects 0.000 description 1
- 230000007310 pathophysiology Effects 0.000 description 1
- 230000008447 perception Effects 0.000 description 1
- 210000000578 peripheral nerve Anatomy 0.000 description 1
- 210000001428 peripheral nervous system Anatomy 0.000 description 1
- 210000002856 peripheral neuron Anatomy 0.000 description 1
- 210000003200 peritoneal cavity Anatomy 0.000 description 1
- 238000011170 pharmaceutical development Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000002831 pharmacologic agent Substances 0.000 description 1
- 238000001050 pharmacotherapy Methods 0.000 description 1
- 229950010883 phencyclidine Drugs 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 230000006461 physiological response Effects 0.000 description 1
- 229960001697 physostigmine Drugs 0.000 description 1
- PIJVFDBKTWXHHD-HIFRSBDPSA-N physostigmine Chemical compound C12=CC(OC(=O)NC)=CC=C2N(C)[C@@H]2[C@@]1(C)CCN2C PIJVFDBKTWXHHD-HIFRSBDPSA-N 0.000 description 1
- 229960001416 pilocarpine Drugs 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 1
- 229960004526 piracetam Drugs 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 125000006684 polyhaloalkyl group Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- VZOPRCCTKLAGPN-ZFJVMAEJSA-L potassium;sodium;(2r,3r)-2,3-dihydroxybutanedioate;tetrahydrate Chemical compound O.O.O.O.[Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O VZOPRCCTKLAGPN-ZFJVMAEJSA-L 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000036278 prepulse Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000007425 progressive decline Effects 0.000 description 1
- 229940097325 prolactin Drugs 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000001107 psychogenic effect Effects 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
- ZSKGQVFRTSEPJT-UHFFFAOYSA-N pyrrole-2-carboxaldehyde Chemical compound O=CC1=CC=CN1 ZSKGQVFRTSEPJT-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 238000001959 radiotherapy Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000000306 recurrent effect Effects 0.000 description 1
- 238000009256 replacement therapy Methods 0.000 description 1
- 206010048628 rheumatoid vasculitis Diseases 0.000 description 1
- 244000195895 saibo Species 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 210000004761 scalp Anatomy 0.000 description 1
- 210000003497 sciatic nerve Anatomy 0.000 description 1
- STECJAGHUSJQJN-FWXGHANASA-N scopolamine Chemical compound C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-FWXGHANASA-N 0.000 description 1
- 229960002646 scopolamine Drugs 0.000 description 1
- 208000012672 seasonal affective disease Diseases 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229960001153 serine Drugs 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 231100000872 sexual dysfunction Toxicity 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 230000006403 short-term memory Effects 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 230000005586 smoking cessation Effects 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 235000011006 sodium potassium tartrate Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 210000000273 spinal nerve root Anatomy 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 208000005809 status epilepticus Diseases 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 208000011117 substance-related disease Diseases 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 210000000106 sweat gland Anatomy 0.000 description 1
- 210000000225 synapse Anatomy 0.000 description 1
- 230000003956 synaptic plasticity Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 229960001685 tacrine Drugs 0.000 description 1
- 229960003565 tacrine hydrochloride Drugs 0.000 description 1
- YLJREFDVOIBQDA-UHFFFAOYSA-O tacrine(1+) Chemical compound C1=CC=C2C([NH3+])=C(CCCC3)C3=NC2=C1 YLJREFDVOIBQDA-UHFFFAOYSA-O 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000002123 temporal effect Effects 0.000 description 1
- MFPWEWYKQYMWRO-UHFFFAOYSA-N tert-butyl carboxy carbonate Chemical compound CC(C)(C)OC(=O)OC(O)=O MFPWEWYKQYMWRO-UHFFFAOYSA-N 0.000 description 1
- HZCHIDSJVMPUQO-UHFFFAOYSA-N tert-butyl-[(5-fluorothiophen-2-yl)methoxymethyl]-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(C(C)(C)C)COCC1=CC=C(F)S1 HZCHIDSJVMPUQO-UHFFFAOYSA-N 0.000 description 1
- MHYGQXWCZAYSLJ-UHFFFAOYSA-N tert-butyl-chloro-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](Cl)(C(C)(C)C)C1=CC=CC=C1 MHYGQXWCZAYSLJ-UHFFFAOYSA-N 0.000 description 1
- ZYDKYFIXEYSNPO-UHFFFAOYSA-N tert-butyl-dimethyl-prop-2-ynoxysilane Chemical compound CC(C)(C)[Si](C)(C)OCC#C ZYDKYFIXEYSNPO-UHFFFAOYSA-N 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- WEMNATFLVGEPEW-UHFFFAOYSA-N thiophene Chemical class C=1C=CSC=1.C=1C=CSC=1 WEMNATFLVGEPEW-UHFFFAOYSA-N 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 208000004371 toothache Diseases 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 238000007070 tosylation reaction Methods 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical group C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 230000001457 vasomotor Effects 0.000 description 1
- 210000001835 viscera Anatomy 0.000 description 1
- 230000031836 visual learning Effects 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- ZFNVDHOSLNRHNN-UHFFFAOYSA-N xi-3-(4-Isopropylphenyl)-2-methylpropanal Chemical compound O=CC(C)CC1=CC=C(C(C)C)C=C1 ZFNVDHOSLNRHNN-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D515/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D515/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D515/04—Ortho-condensed systems
-
- 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
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- 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
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/12—Drugs for genital or sexual disorders; Contraceptives for climacteric disorders
-
- 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
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P29/02—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect
-
- 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
- A61P3/06—Antihyperlipidemics
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Diabetes (AREA)
- Pain & Pain Management (AREA)
- Virology (AREA)
- Obesity (AREA)
- Psychiatry (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Molecular Biology (AREA)
- Oncology (AREA)
- Reproductive Health (AREA)
- Communicable Diseases (AREA)
- Psychology (AREA)
- Child & Adolescent Psychology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Hospice & Palliative Care (AREA)
- Emergency Medicine (AREA)
- Biotechnology (AREA)
- Anesthesiology (AREA)
- Gynecology & Obstetrics (AREA)
- Rheumatology (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US80639106P | 2006-06-30 | 2006-06-30 | |
| US84246506P | 2006-09-05 | 2006-09-05 | |
| US91429307P | 2007-04-26 | 2007-04-26 | |
| PCT/US2007/015396 WO2008005456A2 (en) | 2006-06-30 | 2007-07-02 | Fused heterocyclic inhibitors of d-amino acid oxidase |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009542683A true JP2009542683A (ja) | 2009-12-03 |
| JP2009542683A5 JP2009542683A5 (enExample) | 2010-08-05 |
Family
ID=38877507
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009518342A Pending JP2009542683A (ja) | 2006-06-30 | 2007-07-02 | D−アミノ酸オキシダーゼの縮合ヘテロ環式阻害剤 |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP2057162A2 (enExample) |
| JP (1) | JP2009542683A (enExample) |
| KR (1) | KR20090024823A (enExample) |
| AU (1) | AU2007269646A1 (enExample) |
| BR (1) | BRPI0713216A2 (enExample) |
| CA (1) | CA2659060A1 (enExample) |
| IL (1) | IL195921A0 (enExample) |
| MX (1) | MX2008016525A (enExample) |
| WO (1) | WO2008005456A2 (enExample) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2014522830A (ja) * | 2011-07-07 | 2014-09-08 | 武田薬品工業株式会社 | ピリミジノン化合物およびそれらの使用 |
| JP2014524461A (ja) * | 2011-08-22 | 2014-09-22 | 武田薬品工業株式会社 | ピリダジノン化合物、及びdaao阻害剤としてのその使用 |
| JP2016502998A (ja) * | 2012-12-17 | 2016-02-01 | 武田薬品工業株式会社 | Daao酵素阻害剤としてのピリダジノン |
| KR20220123738A (ko) * | 2014-04-30 | 2022-09-08 | 위펑 제인 쳉 | D-아미노산 옥시다제 억제제로서 공지된 화합물의 용도 |
| JP2022540000A (ja) * | 2019-06-28 | 2022-09-14 | ファイザー・インク | Bckdk阻害活性を有するチエノ[3,2-b]チオフェン-2-カルボン酸化合物 |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2551952A1 (en) | 2003-12-29 | 2005-07-21 | Sepracor Inc. | Pyrrole and pyrazole daao inhibitors |
| WO2007081542A2 (en) | 2006-01-06 | 2007-07-19 | Sepracor Inc. | Tetralone-based monoamine reuptake inhibitors |
| CA2636324C (en) | 2006-01-06 | 2012-03-20 | Sepracor Inc. | Cycloalkylamines as monoamine reuptake inhibitors |
| DK2013835T3 (en) | 2006-03-31 | 2015-12-14 | Sunovion Pharmaceuticals Inc | Preparation of chiral amides and AMINES |
| US7884124B2 (en) | 2006-06-30 | 2011-02-08 | Sepracor Inc. | Fluoro-substituted inhibitors of D-amino acid oxidase |
| US7579370B2 (en) * | 2006-06-30 | 2009-08-25 | Sepracor Inc. | Fused heterocycles |
| EP2077267A4 (en) | 2006-10-18 | 2010-04-07 | Takeda Pharmaceutical | CONDENSED HETEROCYCLIC COMPOUND |
| US7902252B2 (en) * | 2007-01-18 | 2011-03-08 | Sepracor, Inc. | Inhibitors of D-amino acid oxidase |
| RU2470011C2 (ru) | 2007-05-31 | 2012-12-20 | Сепракор Инк. | Циклоалкиламины, содержащие в качестве заместителя фенил, как ингибиторы обратного захвата моноаминов |
| AR076766A1 (es) | 2009-05-14 | 2011-07-06 | Japan Tobacco Inc | Compuestos de azetidina, composiciones farmaceuticas y su uso en el tratamiento de enfermedades autoinmunes. |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001131181A (ja) * | 1999-09-30 | 2001-05-15 | Pfizer Prod Inc | グリコーゲンホスホリラーゼ阻害物質としての二環式ピロリルアミド類 |
| JP2006500394A (ja) * | 2002-09-06 | 2006-01-05 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | チエノピロリルおよびフラノピロリル化合物並びにヒスタミンh4受容体リガンドとしてのそれらの使用 |
| JP2009511462A (ja) * | 2005-10-06 | 2009-03-19 | メルク シャープ エンド ドーム リミテッド | D−アミノ酸酸化酵素阻害剤として神経変性および精神疾患を治療するための縮合ピロールカルボン酸の使用 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9803228D0 (en) * | 1998-02-17 | 1998-04-08 | Zeneca Ltd | Chemical compounds |
| EP1391460A1 (en) * | 1999-09-30 | 2004-02-25 | Pfizer Products Inc. | Tricyclic pyrrolyl amides as glycogen phosphorylase inhibitors |
| US20030162825A1 (en) * | 2001-11-09 | 2003-08-28 | Sepracor Inc. | D-amino acid oxidase inhibitors for learning and memory |
| CA2551952A1 (en) * | 2003-12-29 | 2005-07-21 | Sepracor Inc. | Pyrrole and pyrazole daao inhibitors |
| CA2569530C (en) * | 2004-07-01 | 2013-07-30 | Daiichi Asubio Pharma Co.,Ltd. | Thienopyrazole derivative having pde 7 inhibitory activity |
| CA2594665A1 (en) * | 2005-01-19 | 2006-07-27 | Biolipox Ab | Thienopyrroles useful in the treatment of inflammation |
| UA95788C2 (en) * | 2005-12-15 | 2011-09-12 | Ф. Хоффманн-Ля Рош Аг | Fused pyrrole derivatives |
-
2007
- 2007-07-02 BR BRPI0713216-6A patent/BRPI0713216A2/pt not_active IP Right Cessation
- 2007-07-02 WO PCT/US2007/015396 patent/WO2008005456A2/en not_active Ceased
- 2007-07-02 KR KR1020097001738A patent/KR20090024823A/ko not_active Withdrawn
- 2007-07-02 CA CA002659060A patent/CA2659060A1/en not_active Abandoned
- 2007-07-02 AU AU2007269646A patent/AU2007269646A1/en not_active Abandoned
- 2007-07-02 MX MX2008016525A patent/MX2008016525A/es not_active Application Discontinuation
- 2007-07-02 JP JP2009518342A patent/JP2009542683A/ja active Pending
- 2007-07-02 EP EP07796659A patent/EP2057162A2/en not_active Withdrawn
-
2008
- 2008-12-14 IL IL195921A patent/IL195921A0/en unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001131181A (ja) * | 1999-09-30 | 2001-05-15 | Pfizer Prod Inc | グリコーゲンホスホリラーゼ阻害物質としての二環式ピロリルアミド類 |
| JP2006500394A (ja) * | 2002-09-06 | 2006-01-05 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | チエノピロリルおよびフラノピロリル化合物並びにヒスタミンh4受容体リガンドとしてのそれらの使用 |
| JP2009511462A (ja) * | 2005-10-06 | 2009-03-19 | メルク シャープ エンド ドーム リミテッド | D−アミノ酸酸化酵素阻害剤として神経変性および精神疾患を治療するための縮合ピロールカルボン酸の使用 |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2014522830A (ja) * | 2011-07-07 | 2014-09-08 | 武田薬品工業株式会社 | ピリミジノン化合物およびそれらの使用 |
| JP2014524461A (ja) * | 2011-08-22 | 2014-09-22 | 武田薬品工業株式会社 | ピリダジノン化合物、及びdaao阻害剤としてのその使用 |
| JP2016502998A (ja) * | 2012-12-17 | 2016-02-01 | 武田薬品工業株式会社 | Daao酵素阻害剤としてのピリダジノン |
| US9750748B2 (en) | 2012-12-17 | 2017-09-05 | Takeda Pharmaceutical Company Limited | Pyridazinones as DAAO enzyme inhibitors |
| KR20220123738A (ko) * | 2014-04-30 | 2022-09-08 | 위펑 제인 쳉 | D-아미노산 옥시다제 억제제로서 공지된 화합물의 용도 |
| KR102537686B1 (ko) | 2014-04-30 | 2023-05-30 | 위펑 제인 쳉 | D-아미노산 옥시다제 억제제로서 공지된 화합물의 용도 |
| JP2022540000A (ja) * | 2019-06-28 | 2022-09-14 | ファイザー・インク | Bckdk阻害活性を有するチエノ[3,2-b]チオフェン-2-カルボン酸化合物 |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2007269646A1 (en) | 2008-01-10 |
| EP2057162A2 (en) | 2009-05-13 |
| IL195921A0 (en) | 2009-09-01 |
| MX2008016525A (es) | 2009-03-09 |
| WO2008005456A3 (en) | 2008-07-31 |
| CA2659060A1 (en) | 2008-01-10 |
| BRPI0713216A2 (pt) | 2012-12-04 |
| KR20090024823A (ko) | 2009-03-09 |
| WO2008005456A2 (en) | 2008-01-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2009542683A (ja) | D−アミノ酸オキシダーゼの縮合ヘテロ環式阻害剤 | |
| US7884124B2 (en) | Fluoro-substituted inhibitors of D-amino acid oxidase | |
| US20080058395A1 (en) | Fused heterocyclic inhibitors of D-amino acid oxidase | |
| US7579370B2 (en) | Fused heterocycles | |
| KR102307413B1 (ko) | 다환형 화합물 및 이의 사용 방법 | |
| KR100554817B1 (ko) | 신규한 아자-인돌릴 유도체 | |
| US7902252B2 (en) | Inhibitors of D-amino acid oxidase | |
| US20090099248A1 (en) | Inhibitors of d-amino acid oxidase | |
| WO2010017418A1 (en) | Prodrugs of fused heterocyclic inhibitors of d-amino acid oxidase | |
| WO2016104434A1 (ja) | 複素環化合物 | |
| CN110709401B (zh) | 杂环化合物 | |
| CN101511832A (zh) | D-氨基酸氧化酶的稠合杂环抑制剂 | |
| TW200906833A (en) | Fused heterocyclic inhibitors of D-amino acid oxidase |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20090904 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20100610 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20100610 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20100611 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20121009 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20130712 |