SK1562004A3 - Azabicyklické substituované anelované heteroarylové zlúčeniny na liečenie chorôb - Google Patents

Info

Publication number

SK1562004A3

SK1562004A3 SK156-2004A SK1562004A SK1562004A3 SK 1562004 A3 SK1562004 A3 SK 1562004A3 SK 1562004 A SK1562004 A SK 1562004A SK 1562004 A3 SK1562004 A3 SK 1562004A3

Authority

SK

Slovakia

Prior art keywords

azabicyclo

pyridine

carboxamide

oct

hept

Prior art date

2001-10-02

Links

• Espacenet
• Global Dossier
• Discuss

• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 104
• 201000010099 disease Diseases 0.000 title claims description 65
• 238000011282 treatment Methods 0.000 title claims description 64
• 150000001875 compounds Chemical class 0.000 claims abstract description 301
• 239000000203 mixture Substances 0.000 claims abstract description 190
• 239000003814 drug Substances 0.000 claims abstract description 82
• 150000003839 salts Chemical class 0.000 claims abstract description 47
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract description 25
• -1 thieno [2,3-b] pyridin-2-yl Chemical group 0.000 claims description 576
• 125000000217 alkyl group Chemical group 0.000 claims description 209
• 239000000460 chlorine Substances 0.000 claims description 122
• 125000001424 substituent group Chemical group 0.000 claims description 102
• 229910052801 chlorine Inorganic materials 0.000 claims description 95
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 95
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 83
• 229910052731 fluorine Inorganic materials 0.000 claims description 81
• 229910052794 bromium Inorganic materials 0.000 claims description 77
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 73
• 229910052740 iodine Inorganic materials 0.000 claims description 72
• 238000000034 method Methods 0.000 claims description 71
• 229940079593 drug Drugs 0.000 claims description 69
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 68
• IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims description 65
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 47
• 208000024891 symptom Diseases 0.000 claims description 44
• 229910052757 nitrogen Inorganic materials 0.000 claims description 43
• 229910052739 hydrogen Inorganic materials 0.000 claims description 40
• 208000035475 disorder Diseases 0.000 claims description 39
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 38
• 208000024827 Alzheimer disease Diseases 0.000 claims description 37
• 239000001257 hydrogen Substances 0.000 claims description 37
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 34
• IQQNMLSLUVURHZ-UHFFFAOYSA-N furo[2,3-c]pyridine-5-carboxamide Chemical compound C1=NC(C(=O)N)=CC2=C1OC=C2 IQQNMLSLUVURHZ-UHFFFAOYSA-N 0.000 claims description 34
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 33
• 125000003342 alkenyl group Chemical group 0.000 claims description 32
• 125000000304 alkynyl group Chemical group 0.000 claims description 32
• 125000003118 aryl group Chemical group 0.000 claims description 31
• 239000008194 pharmaceutical composition Substances 0.000 claims description 31
• 239000000164 antipsychotic agent Substances 0.000 claims description 29
• 229910004013 NO 2 Inorganic materials 0.000 claims description 28
• 125000004432 carbon atom Chemical group C* 0.000 claims description 27
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 26
• UZIYZYPHBOMKBY-UHFFFAOYSA-N furo[3,2-c]pyridine-6-carboxamide Chemical compound C1=NC(C(=O)N)=CC2=C1C=CO2 UZIYZYPHBOMKBY-UHFFFAOYSA-N 0.000 claims description 26
• 206010012289 Dementia Diseases 0.000 claims description 24
• 201000000980 schizophrenia Diseases 0.000 claims description 22
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 22
• 208000028017 Psychotic disease Diseases 0.000 claims description 21
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 21
• 241000124008 Mammalia Species 0.000 claims description 20
• 208000002193 Pain Diseases 0.000 claims description 19
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
• 229910052717 sulfur Inorganic materials 0.000 claims description 19
• DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 18
• 150000001408 amides Chemical class 0.000 claims description 18
• 208000010877 cognitive disease Diseases 0.000 claims description 18
• 229910052760 oxygen Inorganic materials 0.000 claims description 18
• 208000010412 Glaucoma Diseases 0.000 claims description 17
• 208000019022 Mood disease Diseases 0.000 claims description 17
• 230000004770 neurodegeneration Effects 0.000 claims description 17
• 206010043118 Tardive Dyskinesia Diseases 0.000 claims description 16
• 239000003795 chemical substances by application Substances 0.000 claims description 16
• 239000000556 agonist Substances 0.000 claims description 14
• 125000005017 substituted alkenyl group Chemical group 0.000 claims description 14
• 229910052799 carbon Inorganic materials 0.000 claims description 13
• 230000003542 behavioural effect Effects 0.000 claims description 12
• 125000004426 substituted alkynyl group Chemical group 0.000 claims description 12
• 208000019901 Anxiety disease Diseases 0.000 claims description 11
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
• 208000023105 Huntington disease Diseases 0.000 claims description 11
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
• 206010039966 Senile dementia Diseases 0.000 claims description 11
• 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims description 11
• 208000027061 mild cognitive impairment Diseases 0.000 claims description 11
• 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 claims description 10
• 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 claims description 10
• 230000036506 anxiety Effects 0.000 claims description 10
• 125000001624 naphthyl group Chemical group 0.000 claims description 10
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
• 201000010374 Down Syndrome Diseases 0.000 claims description 9
• 206010036631 Presenile dementia Diseases 0.000 claims description 9
• 230000008482 dysregulation Effects 0.000 claims description 9
• RLBRZMUOZZGMQL-UHFFFAOYSA-N furo[2,3-b]pyridine-2-carboxamide Chemical compound NC(=O)c1cc2cccnc2o1 RLBRZMUOZZGMQL-UHFFFAOYSA-N 0.000 claims description 9
• 125000005842 heteroatom Chemical group 0.000 claims description 9
• 208000002780 macular degeneration Diseases 0.000 claims description 9
• 230000005586 smoking cessation Effects 0.000 claims description 9
• TUPZWIXDHKKDRH-UHFFFAOYSA-N thieno[3,2-c]pyridine-6-carboxamide Chemical compound C1=NC(C(=O)N)=CC2=C1C=CS2 TUPZWIXDHKKDRH-UHFFFAOYSA-N 0.000 claims description 9
• 208000018737 Parkinson disease Diseases 0.000 claims description 8
• 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 8
• 230000037396 body weight Effects 0.000 claims description 8
• 230000007278 cognition impairment Effects 0.000 claims description 8
• 231100000870 cognitive problem Toxicity 0.000 claims description 8
• MVTCXSGPYZCCHC-UHFFFAOYSA-N furo[2,3-c]pyridine-3,5-dicarboxamide Chemical compound O1C=C(C=2C1=CN=C(C=2)C(=O)N)C(=O)N MVTCXSGPYZCCHC-UHFFFAOYSA-N 0.000 claims description 8
• UORVCLMRJXCDCP-UHFFFAOYSA-M propynoate Chemical compound [O-]C(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-M 0.000 claims description 8
• 208000003174 Brain Neoplasms Diseases 0.000 claims description 7
• 206010006550 Bulimia nervosa Diseases 0.000 claims description 7
• 201000011240 Frontotemporal dementia Diseases 0.000 claims description 7
• 208000000609 Pick Disease of the Brain Diseases 0.000 claims description 7
• 208000030886 Traumatic Brain injury Diseases 0.000 claims description 7
• 206010064930 age-related macular degeneration Diseases 0.000 claims description 7
• 230000037406 food intake Effects 0.000 claims description 7
• 235000012631 food intake Nutrition 0.000 claims description 7
• PAYJWQZDXBKDIP-UHFFFAOYSA-N furo[3,2-c]pyridine-2,6-dicarboxamide Chemical compound O1C(=CC=2C=NC(=CC=21)C(=O)N)C(=O)N PAYJWQZDXBKDIP-UHFFFAOYSA-N 0.000 claims description 7
• 208000028173 post-traumatic stress disease Diseases 0.000 claims description 7
• 208000011580 syndromic disease Diseases 0.000 claims description 7
• CZXIPBIBWCODNX-UHFFFAOYSA-N thieno[2,3-c]pyridine-5-carboxamide Chemical compound C1=NC(C(=O)N)=CC2=C1SC=C2 CZXIPBIBWCODNX-UHFFFAOYSA-N 0.000 claims description 7
• OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 claims description 6
• 229960004373 acetylcholine Drugs 0.000 claims description 6
• 210000004558 lewy body Anatomy 0.000 claims description 6
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
• 230000009529 traumatic brain injury Effects 0.000 claims description 6
• 208000011688 Generalised anxiety disease Diseases 0.000 claims description 5
• 231100000871 behavioral problem Toxicity 0.000 claims description 5
• 208000029364 generalized anxiety disease Diseases 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 5
• BXAUULGWZHMQQD-UHFFFAOYSA-N n-(3-azabicyclo[2.2.1]heptan-5-yl)furo[3,2-c]pyridine-6-carboxamide Chemical compound C1C(C2)CNC2C1NC(=O)C(N=C1)=CC2=C1C=CO2 BXAUULGWZHMQQD-UHFFFAOYSA-N 0.000 claims description 5
• YCGCCACFPSQKTC-UHFFFAOYSA-N n-(3-azabicyclo[2.2.1]heptan-5-yl)thieno[3,2-c]pyridine-2-carboxamide Chemical compound N1=CC=C2SC(C(NC3C4NCC(C4)C3)=O)=CC2=C1 YCGCCACFPSQKTC-UHFFFAOYSA-N 0.000 claims description 5
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 5
• 206010065040 AIDS dementia complex Diseases 0.000 claims description 4
• 208000017194 Affective disease Diseases 0.000 claims description 4
• 208000000103 Anorexia Nervosa Diseases 0.000 claims description 4
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
• VALZEWQNFPSFDY-UHFFFAOYSA-N [1]benzothiolo[3,2-c]pyridine-3-carboxamide Chemical compound S1C2=CC=CC=C2C2=C1C=C(C(=O)N)N=C2 VALZEWQNFPSFDY-UHFFFAOYSA-N 0.000 claims description 4
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
• 239000011737 fluorine Substances 0.000 claims description 4
• CFCQXPSHKBWZAW-UHFFFAOYSA-N n-(1-azabicyclo[2.2.1]heptan-3-yl)-2-methylfuro[2,3-c]pyridine-5-carboxamide Chemical compound C1=C2OC(C)=CC2=CC(C(=O)NC2C3CCN(C3)C2)=N1 CFCQXPSHKBWZAW-UHFFFAOYSA-N 0.000 claims description 4
• QAYBPJFMIGTFCJ-UHFFFAOYSA-N n-(2-azabicyclo[2.2.1]heptan-5-yl)-3-ethylfuro[2,3-c]pyridine-5-carboxamide Chemical compound C1=C2C(CC)=COC2=CN=C1C(=O)NC1C(CN2)CC2C1 QAYBPJFMIGTFCJ-UHFFFAOYSA-N 0.000 claims description 4
• UJCAMMCNOFMQFK-UHFFFAOYSA-N n-(2-azabicyclo[2.2.1]heptan-5-yl)-3-methylfuro[2,3-c]pyridine-5-carboxamide Chemical compound C1=C2C(C)=COC2=CN=C1C(=O)NC1C(CN2)CC2C1 UJCAMMCNOFMQFK-UHFFFAOYSA-N 0.000 claims description 4
• SUHGWRWARRKLAF-UHFFFAOYSA-N n-(2-azabicyclo[2.2.1]heptan-5-yl)furo[2,3-c]pyridine-5-carboxamide Chemical compound C1C(NC2)CC2C1NC(=O)C(N=C1)=CC2=C1OC=C2 SUHGWRWARRKLAF-UHFFFAOYSA-N 0.000 claims description 4
• YQPPJWRWINKNBH-UHFFFAOYSA-N n-(2-azabicyclo[2.2.1]heptan-5-yl)furo[3,2-c]pyridine-6-carboxamide Chemical compound C1C(NC2)CC2C1NC(=O)C(N=C1)=CC2=C1C=CO2 YQPPJWRWINKNBH-UHFFFAOYSA-N 0.000 claims description 4
• WCGLVDJXHZPEDR-UHFFFAOYSA-N n-(2-azabicyclo[2.2.1]heptan-5-yl)thieno[2,3-b]pyridine-6-carboxamide Chemical compound C1=C2C=CSC2=NC(C(NC2C3CC(NC3)C2)=O)=C1 WCGLVDJXHZPEDR-UHFFFAOYSA-N 0.000 claims description 4
• SGIWRTBMGVBZPF-UHFFFAOYSA-N n-(3-azabicyclo[2.2.1]heptan-5-yl)-3-ethylfuro[2,3-c]pyridine-5-carboxamide Chemical compound C1=C2C(CC)=COC2=CN=C1C(=O)NC1C(C2)NCC2C1 SGIWRTBMGVBZPF-UHFFFAOYSA-N 0.000 claims description 4
• OZUHTEWMIOUTAT-UHFFFAOYSA-N n-(3-azabicyclo[2.2.1]heptan-5-yl)furo[2,3-c]pyridine-5-carboxamide Chemical compound C1C(C2)CNC2C1NC(=O)C(N=C1)=CC2=C1OC=C2 OZUHTEWMIOUTAT-UHFFFAOYSA-N 0.000 claims description 4
• IPRBETWGSUMHNJ-UHFFFAOYSA-N n-(3-azabicyclo[2.2.1]heptan-5-yl)thieno[2,3-b]pyridine-5-carboxamide Chemical compound N1=C2SC=CC2=CC(C(NC2C3NCC(C3)C2)=O)=C1 IPRBETWGSUMHNJ-UHFFFAOYSA-N 0.000 claims description 4
• BUHIVGMQHHPOAD-UHFFFAOYSA-N n-(3-azabicyclo[2.2.1]heptan-5-yl)thieno[2,3-b]pyridine-6-carboxamide Chemical compound C1=C2C=CSC2=NC(C(NC2C3NCC(C3)C2)=O)=C1 BUHIVGMQHHPOAD-UHFFFAOYSA-N 0.000 claims description 4
• HMDWNRYMJRVMAM-DGCLKSJQSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-3-ethylfuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC=C2CC HMDWNRYMJRVMAM-DGCLKSJQSA-N 0.000 claims description 4
• PTGWFYYEAUFEAS-ZYHUDNBSSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC=C2 PTGWFYYEAUFEAS-ZYHUDNBSSA-N 0.000 claims description 4
• QMVIATCYBMQPLJ-ZYHUDNBSSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]furo[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=CO2 QMVIATCYBMQPLJ-ZYHUDNBSSA-N 0.000 claims description 4
• GECFKQPBFPRTBN-ZYHUDNBSSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]thieno[2,3-b]pyridine-6-carboxamide Chemical compound C1=C2C=CSC2=NC(C(=O)N[C@H]2CN3CC[C@@](C3)(C2)[H])=C1 GECFKQPBFPRTBN-ZYHUDNBSSA-N 0.000 claims description 4
• XGRYNRMGVCZDEI-TVKKRMFBSA-N n-[(3s)-1-azabicyclo[2.2.1]heptan-3-yl]furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1C2CCN(C2)C1)C(=O)C(N=C1)=CC2=C1OC=C2 XGRYNRMGVCZDEI-TVKKRMFBSA-N 0.000 claims description 4
• 235000005152 nicotinamide Nutrition 0.000 claims description 4
• 239000011570 nicotinamide Substances 0.000 claims description 4
• 125000004076 pyridyl group Chemical group 0.000 claims description 4
• UHADCXYRFWNAIW-UHFFFAOYSA-N thieno[3,2-b]pyridine-6-carboxamide Chemical compound NC(=O)C1=CN=C2C=CSC2=C1 UHADCXYRFWNAIW-UHFFFAOYSA-N 0.000 claims description 4
• YDKTUROIIKITSB-SBXXRYSUSA-N N-[(3S)-1-azabicyclo[2.2.1]heptan-3-yl]-3-ethylfuro[2,3-c]pyridine-5-carboxamide Chemical compound N12C[C@H](C(CC1)C2)NC(=O)C=2C=C1C(=CN2)OC=C1CC YDKTUROIIKITSB-SBXXRYSUSA-N 0.000 claims description 3
• 206010044688 Trisomy 21 Diseases 0.000 claims description 3
• 102000047725 alpha7 Nicotinic Acetylcholine Receptor Human genes 0.000 claims description 3
• 108700006085 alpha7 Nicotinic Acetylcholine Receptor Proteins 0.000 claims description 3
• 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
• 150000001721 carbon Chemical group 0.000 claims description 3
• 210000002816 gill Anatomy 0.000 claims description 3
• SUMSSPBFKITZJS-UHFFFAOYSA-N n-(1-azabicyclo[2.2.1]heptan-3-yl)-2,3-dihydrofuro[2,3-c]pyridine-5-carboxamide Chemical compound C1N(C2)CCC2C1NC(=O)C(N=C1)=CC2=C1OCC2 SUMSSPBFKITZJS-UHFFFAOYSA-N 0.000 claims description 3
• HLKYWLBZPRKGLI-UHFFFAOYSA-N n-(1-azabicyclo[2.2.1]heptan-3-yl)-3,3-dimethyl-2h-furo[2,3-c]pyridine-5-carboxamide Chemical compound C1=C2C(C)(C)COC2=CN=C1C(=O)NC1C(C2)CCN2C1 HLKYWLBZPRKGLI-UHFFFAOYSA-N 0.000 claims description 3
• UISJQFRHOKFCPH-UHFFFAOYSA-N n-(1-azabicyclo[2.2.1]heptan-3-yl)-7-chlorofuro[2,3-c]pyridine-5-carboxamide Chemical compound ClC1=NC(C(=O)NC2C3CCN(C3)C2)=CC2=C1OC=C2 UISJQFRHOKFCPH-UHFFFAOYSA-N 0.000 claims description 3
• ZWQOMVDYVKPFGT-UHFFFAOYSA-N n-(1-azabicyclo[2.2.1]heptan-3-yl)thieno[2,3-b]pyridine-2-carboxamide Chemical compound C1=CN=C2SC(C(NC3C4CCN(C4)C3)=O)=CC2=C1 ZWQOMVDYVKPFGT-UHFFFAOYSA-N 0.000 claims description 3
• FHJCURQHDAPUTC-UHFFFAOYSA-N n-(1-azabicyclo[2.2.1]heptan-3-yl)thieno[2,3-b]pyridine-6-carboxamide Chemical compound C1=C2C=CSC2=NC(C(NC2C3CCN(C3)C2)=O)=C1 FHJCURQHDAPUTC-UHFFFAOYSA-N 0.000 claims description 3
• XIPNELDADKBOAX-UHFFFAOYSA-N n-(1-azabicyclo[2.2.1]heptan-3-yl)thieno[2,3-c]pyridine-2-carboxamide Chemical compound C1=NC=C2SC(C(NC3C4CCN(C4)C3)=O)=CC2=C1 XIPNELDADKBOAX-UHFFFAOYSA-N 0.000 claims description 3
• OTCLLNIQYHKZTM-UHFFFAOYSA-N n-(1-azabicyclo[2.2.1]heptan-3-yl)thieno[3,2-b]pyridine-5-carboxamide Chemical compound C1=C2SC=CC2=NC(C(NC2C3CCN(C3)C2)=O)=C1 OTCLLNIQYHKZTM-UHFFFAOYSA-N 0.000 claims description 3
• STLJFTLTPDKJAD-UHFFFAOYSA-N n-(1-azabicyclo[2.2.1]heptan-3-yl)thieno[3,2-b]pyridine-6-carboxamide Chemical compound N1=C2C=CSC2=CC(C(NC2C3CCN(C3)C2)=O)=C1 STLJFTLTPDKJAD-UHFFFAOYSA-N 0.000 claims description 3
• PIOCVHVCLYFTNA-UHFFFAOYSA-N n-(1-azabicyclo[3.2.2]nonan-3-yl)-2,3-dihydrofuro[2,3-c]pyridine-5-carboxamide Chemical compound C1CN(C2)CCC1CC2NC(=O)C(N=C1)=CC2=C1OCC2 PIOCVHVCLYFTNA-UHFFFAOYSA-N 0.000 claims description 3
• ASWNCLKQEVAEIJ-UHFFFAOYSA-N n-(1-azabicyclo[3.2.2]nonan-3-yl)thieno[2,3-b]pyridine-2-carboxamide Chemical compound C1CN(C2)CCC1CC2NC(=O)C1=CC2=CC=CN=C2S1 ASWNCLKQEVAEIJ-UHFFFAOYSA-N 0.000 claims description 3
• DRFMHBYFHONRDX-UHFFFAOYSA-N n-(1-azabicyclo[3.2.2]nonan-3-yl)thieno[2,3-b]pyridine-6-carboxamide Chemical compound C1CN(C2)CCC1CC2NC(=O)C1=CC=C(C=CS2)C2=N1 DRFMHBYFHONRDX-UHFFFAOYSA-N 0.000 claims description 3
• RSNUCVLHNMEIHO-UHFFFAOYSA-N n-(2-azabicyclo[2.2.1]heptan-5-yl)-2,3-dihydrofuro[2,3-c]pyridine-5-carboxamide Chemical compound C1C(NC2)CC2C1NC(=O)C(N=C1)=CC2=C1OCC2 RSNUCVLHNMEIHO-UHFFFAOYSA-N 0.000 claims description 3
• NCKIAQSJMORJAT-UHFFFAOYSA-N n-(2-azabicyclo[2.2.1]heptan-5-yl)-2-methylfuro[2,3-c]pyridine-5-carboxamide Chemical compound C1=C2OC(C)=CC2=CC(C(=O)NC2C3CC(NC3)C2)=N1 NCKIAQSJMORJAT-UHFFFAOYSA-N 0.000 claims description 3
• IXFRRIIETRNXCK-UHFFFAOYSA-N n-(2-azabicyclo[2.2.1]heptan-5-yl)-3-propan-2-ylfuro[2,3-c]pyridine-5-carboxamide Chemical compound C1=C2C(C(C)C)=COC2=CN=C1C(=O)NC1C(CN2)CC2C1 IXFRRIIETRNXCK-UHFFFAOYSA-N 0.000 claims description 3
• LNFSQVAKAWSSRD-UHFFFAOYSA-N n-(2-azabicyclo[2.2.1]heptan-5-yl)-7-chlorofuro[2,3-c]pyridine-5-carboxamide Chemical compound ClC1=NC(C(=O)NC2C3CC(NC3)C2)=CC2=C1OC=C2 LNFSQVAKAWSSRD-UHFFFAOYSA-N 0.000 claims description 3
• HTEXJTURMFKNDM-UHFFFAOYSA-N n-(2-azabicyclo[2.2.1]heptan-5-yl)furo[2,3-b]pyridine-2-carboxamide Chemical compound C1=CN=C2OC(C(NC3C4CC(NC4)C3)=O)=CC2=C1 HTEXJTURMFKNDM-UHFFFAOYSA-N 0.000 claims description 3
• PNWGUNXVNNPTRY-UHFFFAOYSA-N n-(2-azabicyclo[2.2.1]heptan-5-yl)thieno[2,3-b]pyridine-5-carboxamide Chemical compound N1=C2SC=CC2=CC(C(NC2C3CC(NC3)C2)=O)=C1 PNWGUNXVNNPTRY-UHFFFAOYSA-N 0.000 claims description 3
• MBIXGXIHVLFSSW-UHFFFAOYSA-N n-(2-azabicyclo[2.2.1]heptan-5-yl)thieno[2,3-c]pyridine-5-carboxamide Chemical compound C1C(NC2)CC2C1NC(=O)C(N=C1)=CC2=C1SC=C2 MBIXGXIHVLFSSW-UHFFFAOYSA-N 0.000 claims description 3
• JBRUHXPJHPDEJX-UHFFFAOYSA-N n-(2-azabicyclo[2.2.1]heptan-5-yl)thieno[3,2-b]pyridine-5-carboxamide Chemical compound C1=C2SC=CC2=NC(C(NC2C3CC(NC3)C2)=O)=C1 JBRUHXPJHPDEJX-UHFFFAOYSA-N 0.000 claims description 3
• VEYQHNXVKUAVLF-UHFFFAOYSA-N n-(2-azabicyclo[2.2.1]heptan-5-yl)thieno[3,2-c]pyridine-6-carboxamide Chemical compound C1C(NC2)CC2C1NC(=O)C(N=C1)=CC2=C1C=CS2 VEYQHNXVKUAVLF-UHFFFAOYSA-N 0.000 claims description 3
• VMPOXXPYEZPIFP-UHFFFAOYSA-N n-(3-azabicyclo[2.2.1]heptan-5-yl)-2,3-dihydrofuro[2,3-c]pyridine-5-carboxamide Chemical compound C1C(C2)CNC2C1NC(=O)C(N=C1)=CC2=C1OCC2 VMPOXXPYEZPIFP-UHFFFAOYSA-N 0.000 claims description 3
• SVTLBMKUKYNDSL-UHFFFAOYSA-N n-(3-azabicyclo[2.2.1]heptan-5-yl)-2-methylfuro[2,3-c]pyridine-5-carboxamide Chemical compound C1=C2OC(C)=CC2=CC(C(=O)NC2C3NCC(C3)C2)=N1 SVTLBMKUKYNDSL-UHFFFAOYSA-N 0.000 claims description 3
• CBPFMMGLBKBOPW-UHFFFAOYSA-N n-(3-azabicyclo[2.2.1]heptan-5-yl)-3,3-dimethyl-2h-furo[2,3-c]pyridine-5-carboxamide Chemical compound C1=C2C(C)(C)COC2=CN=C1C(=O)NC1C(C2)NCC2C1 CBPFMMGLBKBOPW-UHFFFAOYSA-N 0.000 claims description 3
• CSTSRAAHIPFVJP-UHFFFAOYSA-N n-(3-azabicyclo[2.2.1]heptan-5-yl)-3-methylfuro[2,3-c]pyridine-5-carboxamide Chemical compound C1=C2C(C)=COC2=CN=C1C(=O)NC1C(C2)NCC2C1 CSTSRAAHIPFVJP-UHFFFAOYSA-N 0.000 claims description 3
• KYQGFPNKEPKXIF-UHFFFAOYSA-N n-(3-azabicyclo[2.2.1]heptan-5-yl)-7-chlorofuro[2,3-c]pyridine-5-carboxamide Chemical compound ClC1=NC(C(=O)NC2C3NCC(C3)C2)=CC2=C1OC=C2 KYQGFPNKEPKXIF-UHFFFAOYSA-N 0.000 claims description 3
• NWHZPUNXNIVHGD-UHFFFAOYSA-N n-(3-azabicyclo[2.2.1]heptan-5-yl)furo[2,3-b]pyridine-2-carboxamide Chemical compound C1=CN=C2OC(C(NC3C4NCC(C4)C3)=O)=CC2=C1 NWHZPUNXNIVHGD-UHFFFAOYSA-N 0.000 claims description 3
• RTYRAYACCCVFLK-UHFFFAOYSA-N n-(3-azabicyclo[2.2.1]heptan-5-yl)thieno[2,3-b]pyridine-2-carboxamide Chemical compound C1=CN=C2SC(C(NC3C4NCC(C4)C3)=O)=CC2=C1 RTYRAYACCCVFLK-UHFFFAOYSA-N 0.000 claims description 3
• JWDYFMVWQRYDOQ-UHFFFAOYSA-N n-(3-azabicyclo[2.2.1]heptan-5-yl)thieno[2,3-c]pyridine-5-carboxamide Chemical compound C1C(C2)CNC2C1NC(=O)C(N=C1)=CC2=C1SC=C2 JWDYFMVWQRYDOQ-UHFFFAOYSA-N 0.000 claims description 3
• NEZKVWDPONTSKX-UHFFFAOYSA-N n-(3-azabicyclo[2.2.1]heptan-5-yl)thieno[3,2-b]pyridine-5-carboxamide Chemical compound C1=C2SC=CC2=NC(C(NC2C3NCC(C3)C2)=O)=C1 NEZKVWDPONTSKX-UHFFFAOYSA-N 0.000 claims description 3
• CWCBOVSKYOLMCY-UHFFFAOYSA-N n-(3-azabicyclo[2.2.1]heptan-5-yl)thieno[3,2-b]pyridine-6-carboxamide Chemical compound N1=C2C=CSC2=CC(C(NC2C3NCC(C3)C2)=O)=C1 CWCBOVSKYOLMCY-UHFFFAOYSA-N 0.000 claims description 3
• XGRYNRMGVCZDEI-KFJBMODSSA-N n-[(3r)-1-azabicyclo[2.2.1]heptan-3-yl]furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@@H]1C2CCN(C2)C1)C(=O)C(N=C1)=CC2=C1OC=C2 XGRYNRMGVCZDEI-KFJBMODSSA-N 0.000 claims description 3
• KNCCZXPKHHBLRS-ZYHUDNBSSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-2,3-dihydrofuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1OCC2 KNCCZXPKHHBLRS-ZYHUDNBSSA-N 0.000 claims description 3
• AZBZVTRQUFCVRK-DGCLKSJQSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-2-methylfuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC(C)=C2 AZBZVTRQUFCVRK-DGCLKSJQSA-N 0.000 claims description 3
• KPKOUWOUCOKWLR-VXGBXAGGSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-3,3-dimethyl-2h-furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1OCC2(C)C KPKOUWOUCOKWLR-VXGBXAGGSA-N 0.000 claims description 3
• XIUHNKYALCBRDG-NXEZZACHSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-3-chlorofuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC=C2Cl XIUHNKYALCBRDG-NXEZZACHSA-N 0.000 claims description 3
• ZCHLHQVYHFPHIF-VXGBXAGGSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-3-methylfuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC=C2C ZCHLHQVYHFPHIF-VXGBXAGGSA-N 0.000 claims description 3
• IZQTXXCWLFVPBE-CHWSQXEVSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-3-propan-2-ylfuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC=C2C(C)C IZQTXXCWLFVPBE-CHWSQXEVSA-N 0.000 claims description 3
• REENQZUMJKLTTI-MWLCHTKSSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-7-chlorofuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1Cl)=CC2=C1OC=C2 REENQZUMJKLTTI-MWLCHTKSSA-N 0.000 claims description 3
• KLCOONYZJWSMJR-ZWNOBZJWSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]thieno[2,3-b]pyridine-5-carboxamide Chemical compound N1=C2SC=CC2=CC(C(=O)N[C@H]2CN3CC[C@@](C3)(C2)[H])=C1 KLCOONYZJWSMJR-ZWNOBZJWSA-N 0.000 claims description 3
• KOAYYDMNZMGYAO-ZYHUDNBSSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]thieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1SC=C2 KOAYYDMNZMGYAO-ZYHUDNBSSA-N 0.000 claims description 3
• WUWXDQWMLKKAAB-GHMZBOCLSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]thieno[3,2-b]pyridine-5-carboxamide Chemical compound C1=C2SC=CC2=NC(C(=O)N[C@H]2CN3CC[C@@](C3)(C2)[H])=C1 WUWXDQWMLKKAAB-GHMZBOCLSA-N 0.000 claims description 3
• RSYULNOZIQJAEW-ZYHUDNBSSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]thieno[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=CS2 RSYULNOZIQJAEW-ZYHUDNBSSA-N 0.000 claims description 3
• ZULBNBDSXRGSBO-JLOHTSLTSA-N n-[(3s)-1-azabicyclo[2.2.1]heptan-3-yl]-3-methylfuro[2,3-c]pyridine-5-carboxamide Chemical compound C1=C2C(C)=COC2=CN=C1C(=O)N[C@H]1C(C2)CCN2C1 ZULBNBDSXRGSBO-JLOHTSLTSA-N 0.000 claims description 3
• VEPNWVXJDUROKQ-UHFFFAOYSA-N thieno[3,4-c]pyridine-6-carboxamide Chemical compound C=1SC=C2C=NC(=CC21)C(=O)N VEPNWVXJDUROKQ-UHFFFAOYSA-N 0.000 claims description 3
• FYMYLEGNHTZXPL-DGCLKSJQSA-N 2-acetyl-n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]thieno[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(C(C)=O)S2 FYMYLEGNHTZXPL-DGCLKSJQSA-N 0.000 claims description 2
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
• 229940122578 Acetylcholine receptor agonist Drugs 0.000 claims description 2
• ZHYWTGZVVOVGDC-JOPIAHFSSA-N N-[(3S)-1-azabicyclo[2.2.1]heptan-3-yl]-3-propan-2-ylfuro[2,3-c]pyridine-5-carboxamide Chemical compound N12C[C@H](C(CC1)C2)NC(=O)C=2C=C1C(=CN2)OC=C1C(C)C ZHYWTGZVVOVGDC-JOPIAHFSSA-N 0.000 claims description 2
• NVJTYLACYONXPS-TVKKRMFBSA-N N-[(3S)-1-azabicyclo[2.2.1]heptan-3-yl]thieno[2,3-c]pyridine-5-carboxamide Chemical compound O=C(N[C@@H]1CN2CCC1C2)c1cc2ccsc2cn1 NVJTYLACYONXPS-TVKKRMFBSA-N 0.000 claims description 2
• NZMHBPQNKRGLGA-UHFFFAOYSA-N [1]benzofuro[2,3-c]pyridine-3-carboxamide Chemical compound O1C2=CC=CC=C2C2=C1C=NC(C(=O)N)=C2 NZMHBPQNKRGLGA-UHFFFAOYSA-N 0.000 claims description 2
• NHANKJDOPVCXFZ-UHFFFAOYSA-N [1]benzothiolo[2,3-c]pyridine-3-carboxamide Chemical compound S1C2=CC=CC=C2C2=C1C=NC(C(=O)N)=C2 NHANKJDOPVCXFZ-UHFFFAOYSA-N 0.000 claims description 2
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
• SGLYJOHWGSYQTC-UHFFFAOYSA-N furo[2,3-c]pyridine-3-carboxylic acid Chemical compound N1=CC=C2C(C(=O)O)=COC2=C1 SGLYJOHWGSYQTC-UHFFFAOYSA-N 0.000 claims description 2
• SPWZDQUIUXNYBL-UHFFFAOYSA-N furo[3,2-c]pyridine-2-carboxylic acid Chemical compound N1=CC=C2OC(C(=O)O)=CC2=C1 SPWZDQUIUXNYBL-UHFFFAOYSA-N 0.000 claims description 2
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 2
• BYBPLULIAIEHMQ-UHFFFAOYSA-N n-(1-azabicyclo[2.2.1]heptan-3-yl)-1h-pyrrolo[2,3-c]pyridine-5-carboxamide Chemical compound C1N(C2)CCC2C1NC(=O)C(N=C1)=CC2=C1NC=C2 BYBPLULIAIEHMQ-UHFFFAOYSA-N 0.000 claims description 2
• PLCAHCVZIQTZGW-UHFFFAOYSA-N n-(1-azabicyclo[2.2.1]heptan-3-yl)-[1]benzothiolo[3,2-c]pyridine-3-carboxamide Chemical compound S1C2=CC=CC=C2C(C=N2)=C1C=C2C(=O)NC1C(C2)CCN2C1 PLCAHCVZIQTZGW-UHFFFAOYSA-N 0.000 claims description 2
• WHZZUMYIOSNBCX-UHFFFAOYSA-N n-(1-azabicyclo[2.2.1]heptan-3-yl)thieno[3,2-b]pyridine-2-carboxamide Chemical compound C1=CC=C2SC(C(NC3C4CCN(C4)C3)=O)=CC2=N1 WHZZUMYIOSNBCX-UHFFFAOYSA-N 0.000 claims description 2
• WVJZNIPRBMCDKQ-UHFFFAOYSA-N n-(1-azabicyclo[2.2.1]heptan-3-yl)thieno[3,2-c]pyridine-2-carboxamide Chemical compound N1=CC=C2SC(C(NC3C4CCN(C4)C3)=O)=CC2=C1 WVJZNIPRBMCDKQ-UHFFFAOYSA-N 0.000 claims description 2
• NPNXDMQDHFOXTB-UHFFFAOYSA-N n-(1-azabicyclo[2.2.1]heptan-3-yl)thieno[3,4-c]pyridine-6-carboxamide Chemical compound C=1C2=CSC=C2C=NC=1C(=O)NC1C(C2)CCN2C1 NPNXDMQDHFOXTB-UHFFFAOYSA-N 0.000 claims description 2
• MGGVTSMYTBRWBD-UHFFFAOYSA-N n-(1-azabicyclo[3.2.2]nonan-3-yl)furo[3,2-c]pyridine-6-carboxamide Chemical class C1CN(C2)CCC1CC2NC(=O)C(N=C1)=CC2=C1C=CO2 MGGVTSMYTBRWBD-UHFFFAOYSA-N 0.000 claims description 2
• GUHXDMFVNUYWCY-UHFFFAOYSA-N n-(1-azabicyclo[3.2.2]nonan-3-yl)thieno[2,3-b]pyridine-5-carboxamide Chemical compound C1CN(C2)CCC1CC2NC(=O)C1=CN=C(SC=C2)C2=C1 GUHXDMFVNUYWCY-UHFFFAOYSA-N 0.000 claims description 2
• PDTGACMGHOMNHT-UHFFFAOYSA-N n-(1-azabicyclo[3.2.2]nonan-3-yl)thieno[3,2-b]pyridine-5-carboxamide Chemical compound C1CN(C2)CCC1CC2NC(=O)C1=CC=C(SC=C2)C2=N1 PDTGACMGHOMNHT-UHFFFAOYSA-N 0.000 claims description 2
• KBRSTIRSKCZNET-UHFFFAOYSA-N n-(2-azabicyclo[2.2.1]heptan-5-yl)-1h-pyrrolo[2,3-c]pyridine-5-carboxamide Chemical compound C1C(NC2)CC2C1NC(=O)C(N=C1)=CC2=C1NC=C2 KBRSTIRSKCZNET-UHFFFAOYSA-N 0.000 claims description 2
• OLPDFZMXXBCWCI-UHFFFAOYSA-N n-(2-azabicyclo[2.2.1]heptan-5-yl)-2-bromofuro[3,2-c]pyridine-6-carboxamide Chemical compound C1=C2OC(Br)=CC2=CN=C1C(=O)NC1C(CN2)CC2C1 OLPDFZMXXBCWCI-UHFFFAOYSA-N 0.000 claims description 2
• JAIAQXANXQLMKJ-UHFFFAOYSA-N n-(2-azabicyclo[2.2.1]heptan-5-yl)-2-cyanofuro[3,2-c]pyridine-6-carboxamide Chemical compound C1C(NC2)CC2C1NC(=O)C(N=C1)=CC2=C1C=C(C#N)O2 JAIAQXANXQLMKJ-UHFFFAOYSA-N 0.000 claims description 2
• VBYJJYJYJMZYMW-UHFFFAOYSA-N n-(2-azabicyclo[2.2.1]heptan-5-yl)-2-iodofuro[3,2-c]pyridine-6-carboxamide Chemical compound C1=C2OC(I)=CC2=CN=C1C(=O)NC1C(CN2)CC2C1 VBYJJYJYJMZYMW-UHFFFAOYSA-N 0.000 claims description 2
• ZQBSHEUJMPMRFG-UHFFFAOYSA-N n-(2-azabicyclo[2.2.1]heptan-5-yl)-2-prop-1-ynylfuro[3,2-c]pyridine-6-carboxamide Chemical compound C1=C2OC(C#CC)=CC2=CN=C1C(=O)NC1C(CN2)CC2C1 ZQBSHEUJMPMRFG-UHFFFAOYSA-N 0.000 claims description 2
• DIBARGOBWVKYBW-UHFFFAOYSA-N n-(2-azabicyclo[2.2.1]heptan-5-yl)-3-(trifluoromethyl)furo[2,3-c]pyridine-5-carboxamide Chemical compound C1=C2C(C(F)(F)F)=COC2=CN=C1C(=O)NC1C(CN2)CC2C1 DIBARGOBWVKYBW-UHFFFAOYSA-N 0.000 claims description 2
• JYDYDPWVFSIELV-UHFFFAOYSA-N n-(2-azabicyclo[2.2.1]heptan-5-yl)-3-bromofuro[2,3-c]pyridine-5-carboxamide Chemical compound C1=C2C(Br)=COC2=CN=C1C(=O)NC1C(CN2)CC2C1 JYDYDPWVFSIELV-UHFFFAOYSA-N 0.000 claims description 2
• YEMPUIWYTDLPCM-UHFFFAOYSA-N n-(2-azabicyclo[2.2.1]heptan-5-yl)-3-chlorofuro[2,3-c]pyridine-5-carboxamide Chemical compound C1=C2C(Cl)=COC2=CN=C1C(=O)NC1C(CN2)CC2C1 YEMPUIWYTDLPCM-UHFFFAOYSA-N 0.000 claims description 2
• LOZINEIDMMJKHX-UHFFFAOYSA-N n-(2-azabicyclo[2.2.1]heptan-5-yl)-3-cyanofuro[2,3-c]pyridine-5-carboxamide Chemical compound C1C(NC2)CC2C1NC(=O)C(N=C1)=CC2=C1OC=C2C#N LOZINEIDMMJKHX-UHFFFAOYSA-N 0.000 claims description 2
• VLOZTBVOUHJMGE-UHFFFAOYSA-N n-(2-azabicyclo[2.2.1]heptan-5-yl)-3-ethenylfuro[2,3-c]pyridine-5-carboxamide Chemical compound C1=C2C(C=C)=COC2=CN=C1C(=O)NC1C(CN2)CC2C1 VLOZTBVOUHJMGE-UHFFFAOYSA-N 0.000 claims description 2
• DLULAXOFMJKKJJ-UHFFFAOYSA-N n-(2-azabicyclo[2.2.1]heptan-5-yl)-3-fluorofuro[2,3-c]pyridine-5-carboxamide Chemical compound C1=C2C(F)=COC2=CN=C1C(=O)NC1C(CN2)CC2C1 DLULAXOFMJKKJJ-UHFFFAOYSA-N 0.000 claims description 2
• DNEWFQAPSZNSAU-UHFFFAOYSA-N n-(2-azabicyclo[2.2.1]heptan-5-yl)-3-iodofuro[2,3-c]pyridine-5-carboxamide Chemical compound C1=C2C(I)=COC2=CN=C1C(=O)NC1C(CN2)CC2C1 DNEWFQAPSZNSAU-UHFFFAOYSA-N 0.000 claims description 2
• NFXBRRYEMJXHLH-UHFFFAOYSA-N n-(2-azabicyclo[2.2.1]heptan-5-yl)-3-prop-1-ynylfuro[2,3-c]pyridine-5-carboxamide Chemical compound C1=C2C(C#CC)=COC2=CN=C1C(=O)NC1C(CN2)CC2C1 NFXBRRYEMJXHLH-UHFFFAOYSA-N 0.000 claims description 2
• PBLBXIJBIDURQY-UHFFFAOYSA-N n-(2-azabicyclo[2.2.1]heptan-5-yl)-[1]benzothiolo[3,2-c]pyridine-3-carboxamide Chemical compound S1C2=CC=CC=C2C(C=N2)=C1C=C2C(=O)NC1C(CN2)CC2C1 PBLBXIJBIDURQY-UHFFFAOYSA-N 0.000 claims description 2
• LZHIYSKYLVWRSD-UHFFFAOYSA-N n-(2-azabicyclo[2.2.1]heptan-5-yl)thieno[2,3-b]pyridine-2-carboxamide Chemical compound C1=CN=C2SC(C(NC3C4CC(NC4)C3)=O)=CC2=C1 LZHIYSKYLVWRSD-UHFFFAOYSA-N 0.000 claims description 2
• ISJMSQWBJLZJMC-UHFFFAOYSA-N n-(2-azabicyclo[2.2.1]heptan-5-yl)thieno[3,2-c]pyridine-2-carboxamide Chemical compound N1=CC=C2SC(C(NC3C4CC(NC4)C3)=O)=CC2=C1 ISJMSQWBJLZJMC-UHFFFAOYSA-N 0.000 claims description 2
• HGAHLJZXRFFHCV-UHFFFAOYSA-N n-(2-azabicyclo[2.2.1]heptan-5-yl)thieno[3,4-c]pyridine-6-carboxamide Chemical compound C=1C2=CSC=C2C=NC=1C(=O)NC1C(CN2)CC2C1 HGAHLJZXRFFHCV-UHFFFAOYSA-N 0.000 claims description 2
• SAAVYJDGJNRCPF-UHFFFAOYSA-N n-(3-azabicyclo[2.2.1]heptan-5-yl)-1-methylpyrrolo[2,3-c]pyridine-5-carboxamide Chemical compound C1=C2N(C)C=CC2=CC(C(=O)NC2C3NCC(C3)C2)=N1 SAAVYJDGJNRCPF-UHFFFAOYSA-N 0.000 claims description 2
• ZMMOVKILQILCCP-UHFFFAOYSA-N n-(3-azabicyclo[2.2.1]heptan-5-yl)-1h-pyrrolo[2,3-c]pyridine-5-carboxamide Chemical compound C1C(C2)CNC2C1NC(=O)C(N=C1)=CC2=C1NC=C2 ZMMOVKILQILCCP-UHFFFAOYSA-N 0.000 claims description 2
• BBUWVXVUHBDPPM-UHFFFAOYSA-N n-(3-azabicyclo[2.2.1]heptan-5-yl)-2-(trifluoromethyl)furo[3,2-c]pyridine-6-carboxamide Chemical compound C1=C2OC(C(F)(F)F)=CC2=CN=C1C(=O)NC1C(C2)NCC2C1 BBUWVXVUHBDPPM-UHFFFAOYSA-N 0.000 claims description 2
• ILBWBTRJNVDIGO-UHFFFAOYSA-N n-(3-azabicyclo[2.2.1]heptan-5-yl)-2-bromofuro[3,2-c]pyridine-6-carboxamide Chemical compound C1=C2OC(Br)=CC2=CN=C1C(=O)NC1C(C2)NCC2C1 ILBWBTRJNVDIGO-UHFFFAOYSA-N 0.000 claims description 2
• XSDYXZJDFHKZOK-UHFFFAOYSA-N n-(3-azabicyclo[2.2.1]heptan-5-yl)-2-chlorofuro[3,2-c]pyridine-6-carboxamide Chemical compound C1=C2OC(Cl)=CC2=CN=C1C(=O)NC1C(C2)NCC2C1 XSDYXZJDFHKZOK-UHFFFAOYSA-N 0.000 claims description 2
• WNBXXSKBZPGGFI-UHFFFAOYSA-N n-(3-azabicyclo[2.2.1]heptan-5-yl)-2-cyanofuro[3,2-c]pyridine-6-carboxamide Chemical compound C1C(C2)CNC2C1NC(=O)C(N=C1)=CC2=C1C=C(C#N)O2 WNBXXSKBZPGGFI-UHFFFAOYSA-N 0.000 claims description 2
• KVMFBERUKIFGFF-UHFFFAOYSA-N n-(3-azabicyclo[2.2.1]heptan-5-yl)-2-ethynylfuro[3,2-c]pyridine-6-carboxamide Chemical compound C1C(C2)CNC2C1NC(=O)C(N=C1)=CC2=C1C=C(C#C)O2 KVMFBERUKIFGFF-UHFFFAOYSA-N 0.000 claims description 2
• ZMINVOCBYCNMGK-UHFFFAOYSA-N n-(3-azabicyclo[2.2.1]heptan-5-yl)-2-fluorofuro[3,2-c]pyridine-6-carboxamide Chemical compound C1=C2OC(F)=CC2=CN=C1C(=O)NC1C(C2)NCC2C1 ZMINVOCBYCNMGK-UHFFFAOYSA-N 0.000 claims description 2
• MSGVPEJUBBSRGP-UHFFFAOYSA-N n-(3-azabicyclo[2.2.1]heptan-5-yl)-2-iodofuro[3,2-c]pyridine-6-carboxamide Chemical compound C1=C2OC(I)=CC2=CN=C1C(=O)NC1C(C2)NCC2C1 MSGVPEJUBBSRGP-UHFFFAOYSA-N 0.000 claims description 2
• GYFPQRKKNOUMCB-UHFFFAOYSA-N n-(3-azabicyclo[2.2.1]heptan-5-yl)-2-prop-1-ynylfuro[3,2-c]pyridine-6-carboxamide Chemical compound C1=C2OC(C#CC)=CC2=CN=C1C(=O)NC1C(C2)NCC2C1 GYFPQRKKNOUMCB-UHFFFAOYSA-N 0.000 claims description 2
• FVGDGVGJBJYIGY-UHFFFAOYSA-N n-(3-azabicyclo[2.2.1]heptan-5-yl)-3-(trifluoromethyl)furo[2,3-c]pyridine-5-carboxamide Chemical compound C1=C2C(C(F)(F)F)=COC2=CN=C1C(=O)NC1C(C2)NCC2C1 FVGDGVGJBJYIGY-UHFFFAOYSA-N 0.000 claims description 2
• XZNHVOFOIRXUSG-UHFFFAOYSA-N n-(3-azabicyclo[2.2.1]heptan-5-yl)-3-bromofuro[2,3-c]pyridine-5-carboxamide Chemical compound C1=C2C(Br)=COC2=CN=C1C(=O)NC1C(C2)NCC2C1 XZNHVOFOIRXUSG-UHFFFAOYSA-N 0.000 claims description 2
• JWFWRAQRWDYUOU-UHFFFAOYSA-N n-(3-azabicyclo[2.2.1]heptan-5-yl)-3-chlorofuro[2,3-c]pyridine-5-carboxamide Chemical compound C1=C2C(Cl)=COC2=CN=C1C(=O)NC1C(C2)NCC2C1 JWFWRAQRWDYUOU-UHFFFAOYSA-N 0.000 claims description 2
• MQIPAGSNGSQLAL-UHFFFAOYSA-N n-(3-azabicyclo[2.2.1]heptan-5-yl)-3-cyanofuro[2,3-c]pyridine-5-carboxamide Chemical compound C1C(C2)CNC2C1NC(=O)C(N=C1)=CC2=C1OC=C2C#N MQIPAGSNGSQLAL-UHFFFAOYSA-N 0.000 claims description 2
• MNKVZOSOCJETGJ-UHFFFAOYSA-N n-(3-azabicyclo[2.2.1]heptan-5-yl)-3-ethenylfuro[2,3-c]pyridine-5-carboxamide Chemical compound C1=C2C(C=C)=COC2=CN=C1C(=O)NC1C(C2)NCC2C1 MNKVZOSOCJETGJ-UHFFFAOYSA-N 0.000 claims description 2
• OMEOMSBZXCGIBO-UHFFFAOYSA-N n-(3-azabicyclo[2.2.1]heptan-5-yl)-3-ethynylfuro[2,3-c]pyridine-5-carboxamide Chemical compound C1C(C2)CNC2C1NC(=O)C(N=C1)=CC2=C1OC=C2C#C OMEOMSBZXCGIBO-UHFFFAOYSA-N 0.000 claims description 2
• MXISYKMEOYRRDY-UHFFFAOYSA-N n-(3-azabicyclo[2.2.1]heptan-5-yl)-3-fluorofuro[2,3-c]pyridine-5-carboxamide Chemical compound C1=C2C(F)=COC2=CN=C1C(=O)NC1C(C2)NCC2C1 MXISYKMEOYRRDY-UHFFFAOYSA-N 0.000 claims description 2
• PFDYMVLMPSDDHW-UHFFFAOYSA-N n-(3-azabicyclo[2.2.1]heptan-5-yl)-3-formylfuro[2,3-c]pyridine-5-carboxamide Chemical compound C1=C2C(C=O)=COC2=CN=C1C(=O)NC1C(C2)NCC2C1 PFDYMVLMPSDDHW-UHFFFAOYSA-N 0.000 claims description 2
• ALIMJFBGDOCMMB-UHFFFAOYSA-N n-(3-azabicyclo[2.2.1]heptan-5-yl)-3-iodofuro[2,3-c]pyridine-5-carboxamide Chemical compound C1=C2C(I)=COC2=CN=C1C(=O)NC1C(C2)NCC2C1 ALIMJFBGDOCMMB-UHFFFAOYSA-N 0.000 claims description 2
• HFCIFCMCUUDWOH-UHFFFAOYSA-N n-(3-azabicyclo[2.2.1]heptan-5-yl)-3-prop-1-ynylfuro[2,3-c]pyridine-5-carboxamide Chemical compound C1=C2C(C#CC)=COC2=CN=C1C(=O)NC1C(C2)NCC2C1 HFCIFCMCUUDWOH-UHFFFAOYSA-N 0.000 claims description 2
• PXLJESGIXCWSOP-UHFFFAOYSA-N n-(3-azabicyclo[2.2.1]heptan-5-yl)-3-propan-2-ylfuro[2,3-c]pyridine-5-carboxamide Chemical compound C1=C2C(C(C)C)=COC2=CN=C1C(=O)NC1C(C2)NCC2C1 PXLJESGIXCWSOP-UHFFFAOYSA-N 0.000 claims description 2
• NMJYVAHNMUHUFI-UHFFFAOYSA-N n-(3-azabicyclo[2.2.1]heptan-5-yl)-[1]benzothiolo[3,2-c]pyridine-3-carboxamide Chemical compound S1C2=CC=CC=C2C(C=N2)=C1C=C2C(=O)NC1C(C2)NCC2C1 NMJYVAHNMUHUFI-UHFFFAOYSA-N 0.000 claims description 2
• IWIGUFUNEGKZIN-UHFFFAOYSA-N n-(3-azabicyclo[2.2.1]heptan-5-yl)thieno[2,3-c]pyridine-2-carboxamide Chemical compound C1=NC=C2SC(C(NC3C4NCC(C4)C3)=O)=CC2=C1 IWIGUFUNEGKZIN-UHFFFAOYSA-N 0.000 claims description 2
• KRDGENZJYCWWHR-UHFFFAOYSA-N n-(3-azabicyclo[2.2.1]heptan-5-yl)thieno[3,4-c]pyridine-6-carboxamide Chemical compound C=1C2=CSC=C2C=NC=1C(=O)NC1C(C2)NCC2C1 KRDGENZJYCWWHR-UHFFFAOYSA-N 0.000 claims description 2
• BMWJXPPYECOQSU-DGCLKSJQSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-1-methylpyrrolo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1N(C)C=C2 BMWJXPPYECOQSU-DGCLKSJQSA-N 0.000 claims description 2
• HGXOQYJTRDEMIP-ZYHUDNBSSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-1h-pyrrolo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1NC=C2 HGXOQYJTRDEMIP-ZYHUDNBSSA-N 0.000 claims description 2
• JAHMWSLCTCRAQM-MWLCHTKSSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-2-(trifluoromethyl)furo[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(C(F)(F)F)O2 JAHMWSLCTCRAQM-MWLCHTKSSA-N 0.000 claims description 2
• SMIVLTRXOIEQDW-MWLCHTKSSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-2-(trifluoromethyl)thieno[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(C(F)(F)F)S2 SMIVLTRXOIEQDW-MWLCHTKSSA-N 0.000 claims description 2
• WPSQFWUFBDNVBK-MWLCHTKSSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-2-bromofuro[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(Br)O2 WPSQFWUFBDNVBK-MWLCHTKSSA-N 0.000 claims description 2
• FEVNGRPXRBQDDH-MWLCHTKSSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-2-chlorofuro[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(Cl)O2 FEVNGRPXRBQDDH-MWLCHTKSSA-N 0.000 claims description 2
• OXKITBJCHYFNFV-MWLCHTKSSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-2-chlorothieno[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(Cl)S2 OXKITBJCHYFNFV-MWLCHTKSSA-N 0.000 claims description 2
• AILAMDCESXISMB-ZYHUDNBSSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-2-cyanofuro[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(C#N)O2 AILAMDCESXISMB-ZYHUDNBSSA-N 0.000 claims description 2
• PRXDBPOZNVSAQK-ZYHUDNBSSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-2-cyanothieno[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(C#N)S2 PRXDBPOZNVSAQK-ZYHUDNBSSA-N 0.000 claims description 2
• IJUQMJCODKNIRJ-DGCLKSJQSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-2-ethenylfuro[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(C=C)O2 IJUQMJCODKNIRJ-DGCLKSJQSA-N 0.000 claims description 2
• LHDTUEIACZKBBS-DGCLKSJQSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-2-ethylfuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC(CC)=C2 LHDTUEIACZKBBS-DGCLKSJQSA-N 0.000 claims description 2
• CJRHYUFGXAGIBS-DGCLKSJQSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-2-ethylfuro[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(CC)O2 CJRHYUFGXAGIBS-DGCLKSJQSA-N 0.000 claims description 2
• JXPHQSRJCZTHAN-DGCLKSJQSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-2-ethynylfuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC(C#C)=C2 JXPHQSRJCZTHAN-DGCLKSJQSA-N 0.000 claims description 2
• LSOPWSVGHCFBPE-DGCLKSJQSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-2-ethynylfuro[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(C#C)O2 LSOPWSVGHCFBPE-DGCLKSJQSA-N 0.000 claims description 2
• NOJMDOODEXZZBS-DGCLKSJQSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-2-ethynylthieno[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(C#C)S2 NOJMDOODEXZZBS-DGCLKSJQSA-N 0.000 claims description 2
• GYGLDUNLQJGGFE-MWLCHTKSSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-2-fluorofuro[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(F)O2 GYGLDUNLQJGGFE-MWLCHTKSSA-N 0.000 claims description 2
• HNVJZDJFRNESMC-MWLCHTKSSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-2-fluorothieno[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(F)S2 HNVJZDJFRNESMC-MWLCHTKSSA-N 0.000 claims description 2
• HKIZYBZKXVCDCM-ZYHUDNBSSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-2-formylfuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC(C=O)=C2 HKIZYBZKXVCDCM-ZYHUDNBSSA-N 0.000 claims description 2
• IZSRWPSBYMWLLY-ZYHUDNBSSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-2-formylfuro[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(C=O)O2 IZSRWPSBYMWLLY-ZYHUDNBSSA-N 0.000 claims description 2
• PMTXVVXYIAIADW-ZYHUDNBSSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-2-formylthieno[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(C=O)S2 PMTXVVXYIAIADW-ZYHUDNBSSA-N 0.000 claims description 2
• RADWLZASCOLZNY-DGCLKSJQSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-2-methylfuro[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(C)O2 RADWLZASCOLZNY-DGCLKSJQSA-N 0.000 claims description 2
• YPDFNJZDSIQNGI-TZMCWYRMSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-2-prop-1-ynylfuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC(C#CC)=C2 YPDFNJZDSIQNGI-TZMCWYRMSA-N 0.000 claims description 2
• QYYKYYRVDCTIFU-TZMCWYRMSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-2-prop-1-ynylfuro[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(C#CC)O2 QYYKYYRVDCTIFU-TZMCWYRMSA-N 0.000 claims description 2
• QOVHVYNXDPUQIT-TZMCWYRMSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-2-prop-1-ynylthieno[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(C#CC)S2 QOVHVYNXDPUQIT-TZMCWYRMSA-N 0.000 claims description 2
• CDZGUFIFAAXJNK-MWLCHTKSSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-2-sulfanylfuro[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(S)O2 CDZGUFIFAAXJNK-MWLCHTKSSA-N 0.000 claims description 2
• GNONFQWHLWYGOM-NXEZZACHSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-3-(trifluoromethyl)furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC=C2C(F)(F)F GNONFQWHLWYGOM-NXEZZACHSA-N 0.000 claims description 2
• CQKNZAZVJDHWKZ-NXEZZACHSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-3-(trifluoromethyl)furo[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1C(C(F)(F)F)=CO2 CQKNZAZVJDHWKZ-NXEZZACHSA-N 0.000 claims description 2
• NSUODROOZZYHOX-NXEZZACHSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-3-bromofuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC=C2Br NSUODROOZZYHOX-NXEZZACHSA-N 0.000 claims description 2
• DEZMKRHGKHNOBY-NXEZZACHSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-3-bromothieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1SC=C2Br DEZMKRHGKHNOBY-NXEZZACHSA-N 0.000 claims description 2
• UOHBUWVWRCXFMI-ZYHUDNBSSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-3-cyanofuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC=C2C#N UOHBUWVWRCXFMI-ZYHUDNBSSA-N 0.000 claims description 2
• XDUJRFFQHLFEEE-ZYHUDNBSSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-3-cyanofuro[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1C(C#N)=CO2 XDUJRFFQHLFEEE-ZYHUDNBSSA-N 0.000 claims description 2
• MKRNJIUOJGUTNX-DGCLKSJQSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-3-ethenylfuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC=C2C=C MKRNJIUOJGUTNX-DGCLKSJQSA-N 0.000 claims description 2
• MVUCDGSOHASWFG-DGCLKSJQSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-3-ethenylthieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1SC=C2C=C MVUCDGSOHASWFG-DGCLKSJQSA-N 0.000 claims description 2
• RHVYGNBFKRJAMQ-DGCLKSJQSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-3-ethylfuro[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1C(CC)=CO2 RHVYGNBFKRJAMQ-DGCLKSJQSA-N 0.000 claims description 2
• UKQSLNRUOMTZFC-DGCLKSJQSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-3-ethynylfuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC=C2C#C UKQSLNRUOMTZFC-DGCLKSJQSA-N 0.000 claims description 2
• ZRUFKHQMYJCMSX-DGCLKSJQSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-3-ethynylfuro[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1C(C#C)=CO2 ZRUFKHQMYJCMSX-DGCLKSJQSA-N 0.000 claims description 2
• FIDCCISNNHKQHG-DGCLKSJQSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-3-ethynylthieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1SC=C2C#C FIDCCISNNHKQHG-DGCLKSJQSA-N 0.000 claims description 2
• JKYFWDKDVNPIDA-NXEZZACHSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-3-fluorofuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC=C2F JKYFWDKDVNPIDA-NXEZZACHSA-N 0.000 claims description 2
• AKFKRJKSXRGBSY-NXEZZACHSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-3-fluorothieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1SC=C2F AKFKRJKSXRGBSY-NXEZZACHSA-N 0.000 claims description 2
• JDHIIDVHVQIMNW-ZYHUDNBSSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-3-formylfuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC=C2C=O JDHIIDVHVQIMNW-ZYHUDNBSSA-N 0.000 claims description 2
• MQZXSAYVKBQZKQ-ZYHUDNBSSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-3-formylthieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1SC=C2C=O MQZXSAYVKBQZKQ-ZYHUDNBSSA-N 0.000 claims description 2
• OVLDNTXEOKGVRI-NXEZZACHSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-3-iodofuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC=C2I OVLDNTXEOKGVRI-NXEZZACHSA-N 0.000 claims description 2
• FKUUZJTUQBPOMT-NXEZZACHSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-3-iodothieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1SC=C2I FKUUZJTUQBPOMT-NXEZZACHSA-N 0.000 claims description 2
• VXYHIVKUZVPSON-VXGBXAGGSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-3-methylfuro[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1C(C)=CO2 VXYHIVKUZVPSON-VXGBXAGGSA-N 0.000 claims description 2
• WJVLVFHVABWEFX-TZMCWYRMSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-3-prop-1-ynylfuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC=C2C#CC WJVLVFHVABWEFX-TZMCWYRMSA-N 0.000 claims description 2
• NDYYHIPYNBJYAU-TZMCWYRMSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-3-prop-1-ynylfuro[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1C(C#CC)=CO2 NDYYHIPYNBJYAU-TZMCWYRMSA-N 0.000 claims description 2
• ITKKBWQLZITTHQ-TZMCWYRMSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-3-prop-1-ynylthieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1SC=C2C#CC ITKKBWQLZITTHQ-TZMCWYRMSA-N 0.000 claims description 2
• ASEWTZJMKWMDDU-NXEZZACHSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-3-sulfanylthieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1SC=C2S ASEWTZJMKWMDDU-NXEZZACHSA-N 0.000 claims description 2
• AUWSMELWLYXLAA-NXEZZACHSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-4-chlorofuro[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1Cl)=CC2=C1C=CO2 AUWSMELWLYXLAA-NXEZZACHSA-N 0.000 claims description 2
• BNDULPAVZACHFO-NXEZZACHSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-4-chlorothieno[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1Cl)=CC2=C1C=CS2 BNDULPAVZACHFO-NXEZZACHSA-N 0.000 claims description 2
• HTONEPWEXPPEJT-GHMZBOCLSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-4-methoxyfuro[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1OC)=CC2=C1C=CO2 HTONEPWEXPPEJT-GHMZBOCLSA-N 0.000 claims description 2
• NFSXBHSPKJUHKF-VXGBXAGGSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-4-methylfuro[3,2-c]pyridine-6-carbothioamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=S)C(N=C1C)=CC2=C1C=CO2 NFSXBHSPKJUHKF-VXGBXAGGSA-N 0.000 claims description 2
• GVCWZKFGRBIUKC-VXGBXAGGSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-4-methylfuro[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1C)=CC2=C1C=CO2 GVCWZKFGRBIUKC-VXGBXAGGSA-N 0.000 claims description 2
• HHYSIQJPPAFWCB-VXGBXAGGSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-4-methylthieno[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1C)=CC2=C1C=CS2 HHYSIQJPPAFWCB-VXGBXAGGSA-N 0.000 claims description 2
• UDRJJQLMUKASBP-MWLCHTKSSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-7-chlorothieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1Cl)=CC2=C1SC=C2 UDRJJQLMUKASBP-MWLCHTKSSA-N 0.000 claims description 2
• SGFWGVAXXGBHAX-ZYHUDNBSSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-7-methoxyfuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1OC)=CC2=C1OC=C2 SGFWGVAXXGBHAX-ZYHUDNBSSA-N 0.000 claims description 2
• VFLJRYNLFYQSRU-ZYHUDNBSSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-7-methoxythieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1OC)=CC2=C1SC=C2 VFLJRYNLFYQSRU-ZYHUDNBSSA-N 0.000 claims description 2
• YAELCJOHLJERDN-DGCLKSJQSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-7-methylfuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1C)=CC2=C1OC=C2 YAELCJOHLJERDN-DGCLKSJQSA-N 0.000 claims description 2
• UWSAQNPKCPJTPQ-DGCLKSJQSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-7-methylthieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1C)=CC2=C1SC=C2 UWSAQNPKCPJTPQ-DGCLKSJQSA-N 0.000 claims description 2
• GGOZOLLGCCOMOZ-ZYHUDNBSSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]furo[2,3-b]pyridine-2-carboxamide Chemical compound C1=CN=C2OC(C(=O)N[C@H]3CN4CC[C@@](C4)(C3)[H])=CC2=C1 GGOZOLLGCCOMOZ-ZYHUDNBSSA-N 0.000 claims description 2
• FIXHTQYSIZLNEX-GHMZBOCLSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]thieno[3,2-b]pyridine-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N[C@H]3CN4CC[C@@](C4)(C3)[H])=CC2=N1 FIXHTQYSIZLNEX-GHMZBOCLSA-N 0.000 claims description 2
• CITWWADKVZIUDE-ZYHUDNBSSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]thieno[3,2-b]pyridine-6-carboxamide Chemical compound N1=C2C=CSC2=CC(C(=O)N[C@H]2CN3CC[C@@](C3)(C2)[H])=C1 CITWWADKVZIUDE-ZYHUDNBSSA-N 0.000 claims description 2
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
• RXGHULSMJIVVTA-UHFFFAOYSA-N thieno[2,3-b]pyridine-2-carboxamide Chemical compound C1=CN=C2SC(C(=O)N)=CC2=C1 RXGHULSMJIVVTA-UHFFFAOYSA-N 0.000 claims description 2
• 239000002759 woven fabric Substances 0.000 claims description 2
• KVOXCIRHGHAVNM-UHFFFAOYSA-N thieno[2,3-b]pyridine-5-carboxamide Chemical compound NC(=O)C1=CN=C2SC=CC2=C1 KVOXCIRHGHAVNM-UHFFFAOYSA-N 0.000 claims 4
• KBWCDRZERIYILQ-TVKKRMFBSA-N N-[(3S)-1-azabicyclo[2.2.1]heptan-3-yl]thieno[3,2-c]pyridine-6-carboxamide Chemical compound N12C[C@H](C(CC1)C2)NC(=O)C2=CC1=C(C=N2)C=CS1 KBWCDRZERIYILQ-TVKKRMFBSA-N 0.000 claims 2
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 2
• JUJSOMXLYYCAON-UHFFFAOYSA-N n-(1-azabicyclo[3.2.2]nonan-3-yl)thieno[3,2-c]pyridine-6-carboxamide Chemical compound C1CN(C2)CCC1CC2NC(=O)C(N=C1)=CC2=C1C=CS2 JUJSOMXLYYCAON-UHFFFAOYSA-N 0.000 claims 2
• PUURRMSCPPYHGA-UHFFFAOYSA-N n-(2-azabicyclo[2.2.1]heptan-5-yl)thieno[3,2-b]pyridine-6-carboxamide Chemical compound N1=C2C=CSC2=CC(C(NC2C3CC(NC3)C2)=O)=C1 PUURRMSCPPYHGA-UHFFFAOYSA-N 0.000 claims 2
• JBVHGIHVMZRRJJ-UHFFFAOYSA-N n-(3-azabicyclo[2.2.1]heptan-5-yl)thieno[3,2-c]pyridine-6-carboxamide Chemical compound C1C(C2)CNC2C1NC(=O)C(N=C1)=CC2=C1C=CS2 JBVHGIHVMZRRJJ-UHFFFAOYSA-N 0.000 claims 2
• KTEXIXPZKKQNSC-UHFFFAOYSA-N thieno[2,3-b]pyridine-6-carboxamide Chemical compound NC(=O)C1=CC=C2C=CSC2=N1 KTEXIXPZKKQNSC-UHFFFAOYSA-N 0.000 claims 2
• 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims 2
• XUCVBCVUQIKODX-VXGBXAGGSA-N 3-acetamido-n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]thieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1SC=C2NC(C)=O XUCVBCVUQIKODX-VXGBXAGGSA-N 0.000 claims 1
• 125000006448 cycloalkyl cycloalkyl group Chemical group 0.000 claims 1
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
• PBABVYPRICJGDY-UHFFFAOYSA-N n-(1-azabicyclo[3.2.2]nonan-3-yl)furo[2,3-c]pyridine-5-carboxamide Chemical compound C1CN(C2)CCC1CC2NC(=O)C(N=C1)=CC2=C1OC=C2 PBABVYPRICJGDY-UHFFFAOYSA-N 0.000 claims 1
• OHKUGMJFVWOBKQ-UHFFFAOYSA-N n-(1-azabicyclo[3.2.2]nonan-3-yl)thieno[2,3-c]pyridine-5-carboxamide Chemical compound C1CN(C2)CCC1CC2NC(=O)C(N=C1)=CC2=C1SC=C2 OHKUGMJFVWOBKQ-UHFFFAOYSA-N 0.000 claims 1
• JWMVIXDBVWDGJO-UHFFFAOYSA-N n-(1-azabicyclo[3.2.2]nonan-3-yl)thieno[3,2-b]pyridine-2-carboxamide Chemical class C1CN(C2)CCC1CC2NC(=O)C1=CC2=NC=CC=C2S1 JWMVIXDBVWDGJO-UHFFFAOYSA-N 0.000 claims 1
• IYQFAERSNXVRMJ-UHFFFAOYSA-N n-(2-azabicyclo[2.2.1]heptan-5-yl)-2-(trifluoromethyl)furo[3,2-c]pyridine-6-carboxamide Chemical compound C1=C2OC(C(F)(F)F)=CC2=CN=C1C(=O)NC1C(CN2)CC2C1 IYQFAERSNXVRMJ-UHFFFAOYSA-N 0.000 claims 1
• FPGBHINVZREIHL-UHFFFAOYSA-N n-(2-azabicyclo[2.2.1]heptan-5-yl)thieno[2,3-c]pyridine-2-carboxamide Chemical compound C1=NC=C2SC(C(NC3C4CC(NC4)C3)=O)=CC2=C1 FPGBHINVZREIHL-UHFFFAOYSA-N 0.000 claims 1
• ZBTJNEFKDBCAKA-MWLCHTKSSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-2-iodothieno[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(I)S2 ZBTJNEFKDBCAKA-MWLCHTKSSA-N 0.000 claims 1
• HGOJHWQYRDVMMA-MWLCHTKSSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-2-sulfanylthieno[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(S)S2 HGOJHWQYRDVMMA-MWLCHTKSSA-N 0.000 claims 1
• KQAJOIDQGKSLFL-NXEZZACHSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-3-(trifluoromethyl)thieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1SC=C2C(F)(F)F KQAJOIDQGKSLFL-NXEZZACHSA-N 0.000 claims 1
• ZEDILXDTHOTBRH-NXEZZACHSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-3-chlorothieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1SC=C2Cl ZEDILXDTHOTBRH-NXEZZACHSA-N 0.000 claims 1
• DZVZZQODDQDLJT-DGCLKSJQSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-7-methylthieno[2,3-c]pyridine-5-carbothioamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=S)C(N=C1C)=CC2=C1SC=C2 DZVZZQODDQDLJT-DGCLKSJQSA-N 0.000 claims 1
• UGFXJHJGPGBAAC-ZYHUDNBSSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]thieno[2,3-c]pyridine-2-carboxamide Chemical compound C1=NC=C2SC(C(=O)N[C@H]3CN4CC[C@@](C4)(C3)[H])=CC2=C1 UGFXJHJGPGBAAC-ZYHUDNBSSA-N 0.000 claims 1
• YRUSEZGLHJOAFH-ZWNOBZJWSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]thieno[3,4-c]pyridine-6-carboxamide Chemical compound C=1C2=CSC=C2C=NC=1C(=O)N[C@H](C1)CN2CC[C@@]1([H])C2 YRUSEZGLHJOAFH-ZWNOBZJWSA-N 0.000 claims 1
• HKSQZEGSMBFHGC-UHFFFAOYSA-N pyrimidine-4-carboxamide Chemical compound NC(=O)C1=CC=NC=N1 HKSQZEGSMBFHGC-UHFFFAOYSA-N 0.000 claims 1
• 229940044601 receptor agonist Drugs 0.000 claims 1
• 239000000018 receptor agonist Substances 0.000 claims 1
• DSARAHGYZHXMQZ-UHFFFAOYSA-N thieno[3,2-b]pyridine-5-carboxamide Chemical class NC(=O)C1=CC=C2SC=CC2=N1 DSARAHGYZHXMQZ-UHFFFAOYSA-N 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 142
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 132
• 239000007787 solid Substances 0.000 description 96
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 95
• 239000000243 solution Substances 0.000 description 83
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 81
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 76
• 230000002829 reductive effect Effects 0.000 description 70
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 67
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 57
• 235000019439 ethyl acetate Nutrition 0.000 description 53
• QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 53
• 239000012044 organic layer Substances 0.000 description 52
• 230000000694 effects Effects 0.000 description 50
• 239000011541 reaction mixture Substances 0.000 description 50
• 235000002639 sodium chloride Nutrition 0.000 description 49
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 46
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 45
• 239000000706 filtrate Substances 0.000 description 45
• 239000003921 oil Substances 0.000 description 41
• 235000019198 oils Nutrition 0.000 description 41
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 40
• 108040006409 acetylcholine-gated cation-selective channel activity proteins Proteins 0.000 description 37
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 36
• 102000015296 acetylcholine-gated cation-selective channel activity proteins Human genes 0.000 description 36
• 230000008878 coupling Effects 0.000 description 36
• 238000010168 coupling process Methods 0.000 description 36
• 238000005859 coupling reaction Methods 0.000 description 36
• 239000010410 layer Substances 0.000 description 35
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 32
• 239000000543 intermediate Substances 0.000 description 32
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
• 239000000741 silica gel Substances 0.000 description 29
• 229910002027 silica gel Inorganic materials 0.000 description 29
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 28
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 27
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 23
• 239000013058 crude material Substances 0.000 description 22
• 150000001412 amines Chemical class 0.000 description 21
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 21
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 21
• 239000011734 sodium Substances 0.000 description 21
• 235000019441 ethanol Nutrition 0.000 description 20
• 238000002360 preparation method Methods 0.000 description 20
• 102000005962 receptors Human genes 0.000 description 20
• 108020003175 receptors Proteins 0.000 description 20
• 229920006395 saturated elastomer Polymers 0.000 description 20
• 239000000725 suspension Substances 0.000 description 19
• 229960004756 ethanol Drugs 0.000 description 18
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 17
• 150000003254 radicals Chemical class 0.000 description 17
• 239000003480 eluent Substances 0.000 description 16
• 230000006735 deficit Effects 0.000 description 14
• 238000010992 reflux Methods 0.000 description 14
• 239000000126 substance Substances 0.000 description 14
• SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 13
• 239000002253 acid Substances 0.000 description 13
• 230000015572 biosynthetic process Effects 0.000 description 13
• 238000010265 fast atom bombardment Methods 0.000 description 13
• 229960002715 nicotine Drugs 0.000 description 13
• SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 13
• 239000011780 sodium chloride Substances 0.000 description 13
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
• WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 12
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 12
• 239000003369 serotonin 5-HT3 receptor antagonist Substances 0.000 description 12
• 238000003786 synthesis reaction Methods 0.000 description 12
• 210000004556 brain Anatomy 0.000 description 11
• 239000012267 brine Substances 0.000 description 11
• 239000012299 nitrogen atmosphere Substances 0.000 description 11
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
• 238000006243 chemical reaction Methods 0.000 description 10
• 239000012141 concentrate Substances 0.000 description 10
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
• 235000019341 magnesium sulphate Nutrition 0.000 description 10
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 10
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
• 239000000047 product Substances 0.000 description 10
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 9
• 210000004027 cell Anatomy 0.000 description 9
• 230000001149 cognitive effect Effects 0.000 description 9
• 239000012458 free base Substances 0.000 description 9
• 239000008177 pharmaceutical agent Substances 0.000 description 9
• 229940076279 serotonin Drugs 0.000 description 9
• 239000002002 slurry Substances 0.000 description 9
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
• NSGDYZCDUPSTQT-UHFFFAOYSA-N N-[5-bromo-1-[(4-fluorophenyl)methyl]-4-methyl-2-oxopyridin-3-yl]cycloheptanecarboxamide Chemical compound Cc1c(Br)cn(Cc2ccc(F)cc2)c(=O)c1NC(=O)C1CCCCCC1 NSGDYZCDUPSTQT-UHFFFAOYSA-N 0.000 description 8
• 235000011089 carbon dioxide Nutrition 0.000 description 8
• 238000003818 flash chromatography Methods 0.000 description 8
• 239000002904 solvent Substances 0.000 description 8
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 7
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
• 239000005557 antagonist Substances 0.000 description 7
• 230000000561 anti-psychotic effect Effects 0.000 description 7
• 229940005529 antipsychotics Drugs 0.000 description 7
• 238000003556 assay Methods 0.000 description 7
• 150000002148 esters Chemical class 0.000 description 7
• 230000000670 limiting effect Effects 0.000 description 7
• 230000015654 memory Effects 0.000 description 7
• 239000002244 precipitate Substances 0.000 description 7
• 229910052708 sodium Inorganic materials 0.000 description 7
• 238000004809 thin layer chromatography Methods 0.000 description 7
• GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 6
• 208000030507 AIDS Diseases 0.000 description 6
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 6
• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
• 208000022531 anorexia Diseases 0.000 description 6
• 239000007864 aqueous solution Substances 0.000 description 6
• 239000003693 atypical antipsychotic agent Substances 0.000 description 6
• 229940127236 atypical antipsychotics Drugs 0.000 description 6
• 239000011575 calcium Substances 0.000 description 6
• 229960001701 chloroform Drugs 0.000 description 6
• 238000001816 cooling Methods 0.000 description 6
• 206010061428 decreased appetite Diseases 0.000 description 6
• UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
• 230000002496 gastric effect Effects 0.000 description 6
• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
• XLTANAWLDBYGFU-UHFFFAOYSA-N methyllycaconitine hydrochloride Natural products C1CC(OC)C2(C3C4OC)C5CC(C(C6)OC)C(OC)C5C6(O)C4(O)C2N(CC)CC31COC(=O)C1=CC=CC=C1N1C(=O)CC(C)C1=O XLTANAWLDBYGFU-UHFFFAOYSA-N 0.000 description 6
• 150000002923 oximes Chemical class 0.000 description 6
• 230000000698 schizophrenic effect Effects 0.000 description 6
• 239000003826 tablet Substances 0.000 description 6
• 238000002560 therapeutic procedure Methods 0.000 description 6
• QZHXIGDVIINLKX-UHFFFAOYSA-N 2-chloro-6-(hydroxymethyl)-4-iodopyridin-3-ol Chemical compound OCC1=CC(I)=C(O)C(Cl)=N1 QZHXIGDVIINLKX-UHFFFAOYSA-N 0.000 description 5
• 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 description 5
• 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 description 5
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 5
• 108091006146 Channels Proteins 0.000 description 5
• 206010010904 Convulsion Diseases 0.000 description 5
• 206010012239 Delusion Diseases 0.000 description 5
• PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 5
• 239000007821 HATU Substances 0.000 description 5
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 5
• 208000026139 Memory disease Diseases 0.000 description 5
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
• 206010047700 Vomiting Diseases 0.000 description 5
• 239000000935 antidepressant agent Substances 0.000 description 5
• 229940005513 antidepressants Drugs 0.000 description 5
• 125000004429 atom Chemical group 0.000 description 5
• 229910052791 calcium Inorganic materials 0.000 description 5
• 230000003197 catalytic effect Effects 0.000 description 5
• 210000003169 central nervous system Anatomy 0.000 description 5
• 230000001713 cholinergic effect Effects 0.000 description 5
• 230000019771 cognition Effects 0.000 description 5
• 239000012230 colorless oil Substances 0.000 description 5
• 238000002648 combination therapy Methods 0.000 description 5
• 239000012043 crude product Substances 0.000 description 5
• 231100000868 delusion Toxicity 0.000 description 5
• IZLZCXOWFDCZLD-UHFFFAOYSA-N furo[2,3-b]pyridine-2-carboxylic acid Chemical compound C1=CN=C2OC(C(=O)O)=CC2=C1 IZLZCXOWFDCZLD-UHFFFAOYSA-N 0.000 description 5
• BEVAEUJOJMQCIU-UHFFFAOYSA-N furo[2,3-c]pyridine-5-carboxylic acid Chemical compound C1=NC(C(=O)O)=CC2=C1OC=C2 BEVAEUJOJMQCIU-UHFFFAOYSA-N 0.000 description 5
• LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 5
• 230000001965 increasing effect Effects 0.000 description 5
• 229910052744 lithium Inorganic materials 0.000 description 5
• 231100000252 nontoxic Toxicity 0.000 description 5
• 230000003000 nontoxic effect Effects 0.000 description 5
• 229910000027 potassium carbonate Inorganic materials 0.000 description 5
• 125000006239 protecting group Chemical group 0.000 description 5
• 229940044551 receptor antagonist Drugs 0.000 description 5
• 239000002464 receptor antagonist Substances 0.000 description 5
• 238000006467 substitution reaction Methods 0.000 description 5
• 230000004584 weight gain Effects 0.000 description 5
• 235000019786 weight gain Nutrition 0.000 description 5
• BDKLKNJTMLIAFE-UHFFFAOYSA-N 2-(3-fluorophenyl)-1,3-oxazole-4-carbaldehyde Chemical compound FC1=CC=CC(C=2OC=C(C=O)N=2)=C1 BDKLKNJTMLIAFE-UHFFFAOYSA-N 0.000 description 4
• FZLSDZZNPXXBBB-KDURUIRLSA-N 5-chloro-N-[3-cyclopropyl-5-[[(3R,5S)-3,5-dimethylpiperazin-1-yl]methyl]phenyl]-4-(6-methyl-1H-indol-3-yl)pyrimidin-2-amine Chemical compound C[C@H]1CN(Cc2cc(Nc3ncc(Cl)c(n3)-c3c[nH]c4cc(C)ccc34)cc(c2)C2CC2)C[C@@H](C)N1 FZLSDZZNPXXBBB-KDURUIRLSA-N 0.000 description 4
• PXTZUYPPAYUOEY-UHFFFAOYSA-N 7-chlorofuro[2,3-c]pyridine-5-carboxylic acid Chemical compound ClC1=NC(C(=O)O)=CC2=C1OC=C2 PXTZUYPPAYUOEY-UHFFFAOYSA-N 0.000 description 4
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
• 206010067889 Dementia with Lewy bodies Diseases 0.000 description 4
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
• 208000004547 Hallucinations Diseases 0.000 description 4
• 108090000862 Ion Channels Proteins 0.000 description 4
• 102000004310 Ion Channels Human genes 0.000 description 4
• 201000002832 Lewy body dementia Diseases 0.000 description 4
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
• 206010028813 Nausea Diseases 0.000 description 4
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
• 206010039897 Sedation Diseases 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
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
• 208000000323 Tourette Syndrome Diseases 0.000 description 4
• 206010044565 Tremor Diseases 0.000 description 4
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
• 229960000583 acetic acid Drugs 0.000 description 4
• 235000011054 acetic acid Nutrition 0.000 description 4
• 239000004480 active ingredient Substances 0.000 description 4
• 150000001299 aldehydes Chemical class 0.000 description 4
• 150000008064 anhydrides Chemical class 0.000 description 4
• 230000003474 anti-emetic effect Effects 0.000 description 4
• 239000002585 base Substances 0.000 description 4
• 230000027455 binding Effects 0.000 description 4
• 239000011203 carbon fibre reinforced carbon Substances 0.000 description 4
• 150000003857 carboxamides Chemical class 0.000 description 4
• 239000003054 catalyst Substances 0.000 description 4
• 238000004587 chromatography analysis Methods 0.000 description 4
• 230000003920 cognitive function Effects 0.000 description 4
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 4
• 239000003085 diluting agent Substances 0.000 description 4
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
• 206010013663 drug dependence Diseases 0.000 description 4
• ZZEHSWOSYCXPIE-UHFFFAOYSA-N ethyl 3-hydroxyfuro[2,3-b]pyridine-2-carboxylate Chemical compound C1=CC=C2C(O)=C(C(=O)OCC)OC2=N1 ZZEHSWOSYCXPIE-UHFFFAOYSA-N 0.000 description 4
• 235000013305 food Nutrition 0.000 description 4
• 238000009472 formulation Methods 0.000 description 4
• 230000006870 function Effects 0.000 description 4
• CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 4
• 208000013403 hyperactivity Diseases 0.000 description 4
• 150000002466 imines Chemical class 0.000 description 4
• 150000002475 indoles Chemical class 0.000 description 4
• 239000011630 iodine Substances 0.000 description 4
• 150000002500 ions Chemical class 0.000 description 4
• 230000013016 learning Effects 0.000 description 4
• 239000000463 material Substances 0.000 description 4
• 230000008693 nausea Effects 0.000 description 4
• KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 4
• 239000000843 powder Substances 0.000 description 4
• 208000020016 psychiatric disease Diseases 0.000 description 4
• 230000036280 sedation Effects 0.000 description 4
• 239000000377 silicon dioxide Substances 0.000 description 4
• 230000000391 smoking effect Effects 0.000 description 4
• 235000017281 sodium acetate Nutrition 0.000 description 4
• 229940087562 sodium acetate trihydrate Drugs 0.000 description 4
• 229910052938 sodium sulfate Inorganic materials 0.000 description 4
• 235000011152 sodium sulphate Nutrition 0.000 description 4
• 230000000707 stereoselective effect Effects 0.000 description 4
• VJENICOVWOKEGT-UHFFFAOYSA-N (2-trimethylsilylfuro[2,3-c]pyridin-5-yl)methanol Chemical compound OCC1=NC=C2OC([Si](C)(C)C)=CC2=C1 VJENICOVWOKEGT-UHFFFAOYSA-N 0.000 description 3
• PKUGOEKKIILFPA-UHFFFAOYSA-N (3-methyl-2,3-dihydrofuro[2,3-c]pyridin-5-yl)methyl acetate Chemical compound N1=C(COC(C)=O)C=C2C(C)COC2=C1 PKUGOEKKIILFPA-UHFFFAOYSA-N 0.000 description 3
• JIPATFUJPNFNLZ-UHFFFAOYSA-N (3-methylfuro[2,3-c]pyridin-5-yl)methanol Chemical compound N1=C(CO)C=C2C(C)=COC2=C1 JIPATFUJPNFNLZ-UHFFFAOYSA-N 0.000 description 3
• YSMXJEKOIIULPX-UHFFFAOYSA-N (6-chloro-4-iodo-5-prop-2-enoxypyridin-2-yl)methanol Chemical compound OCC1=CC(I)=C(OCC=C)C(Cl)=N1 YSMXJEKOIIULPX-UHFFFAOYSA-N 0.000 description 3
• VJPCATMALHOQOZ-UHFFFAOYSA-N (7-chloro-2-methylfuro[2,3-c]pyridin-5-yl)methanol Chemical compound OCC1=NC(Cl)=C2OC(C)=CC2=C1 VJPCATMALHOQOZ-UHFFFAOYSA-N 0.000 description 3
• LBIISAARLQVUQA-UHFFFAOYSA-N (7-chloro-3,3-dimethyl-2h-furo[2,3-c]pyridin-5-yl)methanol Chemical compound C1=C(CO)N=C(Cl)C2=C1C(C)(C)CO2 LBIISAARLQVUQA-UHFFFAOYSA-N 0.000 description 3
• JYTYBRREMOCQHE-UHFFFAOYSA-N (7-chlorofuro[2,3-c]pyridin-5-yl)methanol Chemical compound ClC1=NC(CO)=CC2=C1OC=C2 JYTYBRREMOCQHE-UHFFFAOYSA-N 0.000 description 3
• IDFPQEHZYBXIFO-GFCCVEGCSA-N (R)-(4-fluoro-2-propylphenyl)-(1H-imidazol-2-yl)methanol Chemical compound CCCc1cc(F)ccc1[C@@H](O)c1ncc[nH]1 IDFPQEHZYBXIFO-GFCCVEGCSA-N 0.000 description 3
• ZKMZPXWMMSBLNO-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-one Chemical compound C1CC2C(=O)CN1CC2 ZKMZPXWMMSBLNO-UHFFFAOYSA-N 0.000 description 3
• NQELPILICRHYOE-UHFFFAOYSA-N 2-chloro-6-(hydroxymethyl)pyridin-3-ol Chemical compound OCC1=CC=C(O)C(Cl)=N1 NQELPILICRHYOE-UHFFFAOYSA-N 0.000 description 3
• IMQBZSJLELBSRO-UHFFFAOYSA-N 3,3-dimethyl-2h-furo[2,3-c]pyridine-5-carbaldehyde Chemical compound N1=C(C=O)C=C2C(C)(C)COC2=C1 IMQBZSJLELBSRO-UHFFFAOYSA-N 0.000 description 3
• BXKYFUGAAFLYJL-BXGYHSFXSA-N 3-[(5e)-5-[(2,4-dimethoxyphenyl)methylidene]-3,4-dihydro-2h-pyridin-6-yl]pyridine;dihydrochloride Chemical compound Cl.Cl.COC1=CC(OC)=CC=C1\C=C/1C(C=2C=NC=CC=2)=NCCC\1 BXKYFUGAAFLYJL-BXGYHSFXSA-N 0.000 description 3
• GXWYGAIVEGCARB-UHFFFAOYSA-N 3-ethylfuro[2,3-c]pyridine-5-carboxylic acid Chemical compound N1=C(C(O)=O)C=C2C(CC)=COC2=C1 GXWYGAIVEGCARB-UHFFFAOYSA-N 0.000 description 3
• JPPLSMNLMJCFBS-UHFFFAOYSA-N 3-methylfuro[2,3-c]pyridine-5-carbaldehyde Chemical compound N1=C(C=O)C=C2C(C)=COC2=C1 JPPLSMNLMJCFBS-UHFFFAOYSA-N 0.000 description 3
• JKHZOVOHNKSEQG-UHFFFAOYSA-N 3-methylfuro[2,3-c]pyridine-5-carboxylic acid Chemical compound N1=C(C(O)=O)C=C2C(C)=COC2=C1 JKHZOVOHNKSEQG-UHFFFAOYSA-N 0.000 description 3
• 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 description 3
• QBZPLRCENXPNIR-UHFFFAOYSA-N 7-chlorofuro[2,3-c]pyridine-5-carbaldehyde Chemical compound ClC1=NC(C=O)=CC2=C1OC=C2 QBZPLRCENXPNIR-UHFFFAOYSA-N 0.000 description 3
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
• 208000020925 Bipolar disease Diseases 0.000 description 3
• 208000032841 Bulimia Diseases 0.000 description 3
• 101000783401 Bungarus multicinctus Alpha-bungarotoxin Proteins 0.000 description 3
• 229910021595 Copper(I) iodide Inorganic materials 0.000 description 3
• 206010012335 Dependence Diseases 0.000 description 3
• PLDUPXSUYLZYBN-UHFFFAOYSA-N Fluphenazine Chemical compound C1CN(CCO)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 PLDUPXSUYLZYBN-UHFFFAOYSA-N 0.000 description 3
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
• 208000019695 Migraine disease Diseases 0.000 description 3
• 102000010909 Monoamine Oxidase Human genes 0.000 description 3
• 108010062431 Monoamine oxidase Proteins 0.000 description 3
• 229940123685 Monoamine oxidase inhibitor Drugs 0.000 description 3
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 3
• 208000021017 Weight Gain Diseases 0.000 description 3
• GSTWPWWOLRJLFK-UHFFFAOYSA-N [6-chloro-4-iodo-5-(2-methylprop-2-enoxy)pyridin-2-yl]methanol Chemical compound CC(=C)COC1=C(Cl)N=C(CO)C=C1I GSTWPWWOLRJLFK-UHFFFAOYSA-N 0.000 description 3
• 102000034337 acetylcholine receptors Human genes 0.000 description 3
• 208000013404 behavioral symptom Diseases 0.000 description 3
• 239000002775 capsule Substances 0.000 description 3
• 239000000969 carrier Substances 0.000 description 3
• 239000007795 chemical reaction product Substances 0.000 description 3
• 235000015218 chewing gum Nutrition 0.000 description 3
• 235000019504 cigarettes Nutrition 0.000 description 3
• 229960004170 clozapine Drugs 0.000 description 3
• QZUDBNBUXVUHMW-UHFFFAOYSA-N clozapine Chemical compound C1CN(C)CCN1C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12 QZUDBNBUXVUHMW-UHFFFAOYSA-N 0.000 description 3
• LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 3
• 125000004122 cyclic group Chemical group 0.000 description 3
• 238000006073 displacement reaction Methods 0.000 description 3
• 239000003937 drug carrier Substances 0.000 description 3
• AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 3
• FRAKJSUXVQJONI-UHFFFAOYSA-N ethyl furo[2,3-b]pyridine-2-carboxylate Chemical compound C1=CN=C2OC(C(=O)OCC)=CC2=C1 FRAKJSUXVQJONI-UHFFFAOYSA-N 0.000 description 3
• 239000000284 extract Substances 0.000 description 3
• 239000012065 filter cake Substances 0.000 description 3
• 238000001914 filtration Methods 0.000 description 3
• 210000002196 fr. b Anatomy 0.000 description 3
• 238000002825 functional assay Methods 0.000 description 3
• LKXRQBNEOKIHRW-UHFFFAOYSA-N furo[2,3-c]pyridine-5-carbaldehyde Chemical compound C1=NC(C=O)=CC2=C1OC=C2 LKXRQBNEOKIHRW-UHFFFAOYSA-N 0.000 description 3
• BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 3
• 230000002068 genetic effect Effects 0.000 description 3
• 125000000623 heterocyclic group Chemical group 0.000 description 3
• 238000004128 high performance liquid chromatography Methods 0.000 description 3
• 210000001320 hippocampus Anatomy 0.000 description 3
• 230000003993 interaction Effects 0.000 description 3
• 239000007788 liquid Substances 0.000 description 3
• 206010027599 migraine Diseases 0.000 description 3
• 239000002899 monoamine oxidase inhibitor Substances 0.000 description 3
• 230000001537 neural effect Effects 0.000 description 3
• 239000000181 nicotinic agonist Substances 0.000 description 3
• 230000000144 pharmacologic effect Effects 0.000 description 3
• 239000002243 precursor Substances 0.000 description 3
• 150000003141 primary amines Chemical class 0.000 description 3
• 230000008569 process Effects 0.000 description 3
• 238000011321 prophylaxis Methods 0.000 description 3
• 108090000623 proteins and genes Proteins 0.000 description 3
• 238000000746 purification Methods 0.000 description 3
• 230000009467 reduction Effects 0.000 description 3
• 239000011347 resin Substances 0.000 description 3
• 229920005989 resin Polymers 0.000 description 3
• 230000009151 sensory gating Effects 0.000 description 3
• 235000017557 sodium bicarbonate Nutrition 0.000 description 3
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
• 239000012312 sodium hydride Substances 0.000 description 3
• 229910000104 sodium hydride Inorganic materials 0.000 description 3
• SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 3
• 208000011117 substance-related disease Diseases 0.000 description 3
• CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 3
• 150000007970 thio esters Chemical class 0.000 description 3
• 150000003556 thioamides Chemical class 0.000 description 3
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
• 230000000472 traumatic effect Effects 0.000 description 3
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 3
• ATOORYZBTGJGEL-UHFFFAOYSA-N (3,3-dimethyl-2h-furo[2,3-c]pyridin-5-yl)methanol Chemical compound N1=C(CO)C=C2C(C)(C)COC2=C1 ATOORYZBTGJGEL-UHFFFAOYSA-N 0.000 description 2
• FFKPQRMZZJGVRU-UHFFFAOYSA-N (3-methyl-2,3-dihydrofuro[2,3-c]pyridin-5-yl)methanol Chemical compound N1=C(CO)C=C2C(C)COC2=C1 FFKPQRMZZJGVRU-UHFFFAOYSA-N 0.000 description 2
• FELGMEQIXOGIFQ-CYBMUJFWSA-N (3r)-9-methyl-3-[(2-methylimidazol-1-yl)methyl]-2,3-dihydro-1h-carbazol-4-one Chemical compound CC1=NC=CN1C[C@@H]1C(=O)C(C=2C(=CC=CC=2)N2C)=C2CC1 FELGMEQIXOGIFQ-CYBMUJFWSA-N 0.000 description 2
• YXBQZBXTBLRJKZ-FYZOBXCZSA-N (5r)-1-azabicyclo[3.2.1]octan-3-one;hydrochloride Chemical compound Cl.C1N2CC[C@]1([H])CC(=O)C2 YXBQZBXTBLRJKZ-FYZOBXCZSA-N 0.000 description 2
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
• LZEPFDKCZQKGBT-UHFFFAOYSA-N 1-azabicyclo[2.2.1]heptan-3-amine Chemical class C1CC2C(N)CN1C2 LZEPFDKCZQKGBT-UHFFFAOYSA-N 0.000 description 2
• LVJFNUWSKALVNL-UHFFFAOYSA-N 1-azabicyclo[3.2.1]octan-3-amine Chemical class C1C(N)CC2CCN1C2 LVJFNUWSKALVNL-UHFFFAOYSA-N 0.000 description 2
• KNHZVHKPTBBLRA-UHFFFAOYSA-N 1-azabicyclo[3.2.1]octan-3-one Chemical compound C1C(=O)CC2CCN1C2 KNHZVHKPTBBLRA-UHFFFAOYSA-N 0.000 description 2
• YXBQZBXTBLRJKZ-UHFFFAOYSA-N 1-azabicyclo[3.2.1]octan-3-one;hydrochloride Chemical compound Cl.C1C(=O)CC2CCN1C2 YXBQZBXTBLRJKZ-UHFFFAOYSA-N 0.000 description 2
• USMDCCKFBJQYKA-UHFFFAOYSA-N 1-azabicyclo[3.2.2]nonan-3-one Chemical compound C1C(=O)CC2CCN1CC2 USMDCCKFBJQYKA-UHFFFAOYSA-N 0.000 description 2
• WSWXGLJGQDOZOL-UHFFFAOYSA-N 2,3-dihydrofuro[2,3-c]pyridine-5-carboxylic acid Chemical compound C1=NC(C(=O)O)=CC2=C1OCC2 WSWXGLJGQDOZOL-UHFFFAOYSA-N 0.000 description 2
• CAGGLVAWUUHLEY-UHFFFAOYSA-N 2-(1,3-dioxolan-2-yl)furan-3-carbaldehyde Chemical compound C1=COC(C2OCCO2)=C1C=O CAGGLVAWUUHLEY-UHFFFAOYSA-N 0.000 description 2
• CQSRCIILSKBLOI-UHFFFAOYSA-N 2-(3-bromofuran-2-yl)-1,3-dioxolane Chemical compound C1=COC(C2OCCO2)=C1Br CQSRCIILSKBLOI-UHFFFAOYSA-N 0.000 description 2
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
• UPUKXPTXCGNQJR-UHFFFAOYSA-N 2-chloro-6-(hydroxymethyl)-4-(2-trimethylsilylethynyl)pyridin-3-ol Chemical compound C[Si](C)(C)C#CC1=CC(CO)=NC(Cl)=C1O UPUKXPTXCGNQJR-UHFFFAOYSA-N 0.000 description 2
• KHPAGGHFIDLUMB-UHFFFAOYSA-N 2-chloropyridine-3-carbaldehyde Chemical compound ClC1=NC=CC=C1C=O KHPAGGHFIDLUMB-UHFFFAOYSA-N 0.000 description 2
• BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 2
• IOVCQYVRHJGXFE-UHFFFAOYSA-N 2-methylfuro[2,3-c]pyridine-5-carbaldehyde Chemical compound O=CC1=NC=C2OC(C)=CC2=C1 IOVCQYVRHJGXFE-UHFFFAOYSA-N 0.000 description 2
• OQOINWAKHMHHTO-UHFFFAOYSA-N 2-methylfuro[2,3-c]pyridine-5-carboxylic acid Chemical compound OC(=O)C1=NC=C2OC(C)=CC2=C1 OQOINWAKHMHHTO-UHFFFAOYSA-N 0.000 description 2
• JIZRGGUCOQKGQD-UHFFFAOYSA-N 2-nitrothiophene Chemical compound [O-][N+](=O)C1=CC=CS1 JIZRGGUCOQKGQD-UHFFFAOYSA-N 0.000 description 2
• NGLYQLOQMWMXAE-UHFFFAOYSA-N 3,3-dimethyl-2h-furo[2,3-c]pyridine-5-carboxylic acid Chemical compound N1=C(C(O)=O)C=C2C(C)(C)COC2=C1 NGLYQLOQMWMXAE-UHFFFAOYSA-N 0.000 description 2
• KSAVZSUPQGDMRC-UHFFFAOYSA-N 3-bromofuran-2-carbaldehyde Chemical compound BrC=1C=COC=1C=O KSAVZSUPQGDMRC-UHFFFAOYSA-N 0.000 description 2
• UYBOQGYUHATTJC-UHFFFAOYSA-N 3-propan-2-ylfuro[2,3-c]pyridine-5-carboxylic acid Chemical compound N1=C(C(O)=O)C=C2C(C(C)C)=COC2=C1 UYBOQGYUHATTJC-UHFFFAOYSA-N 0.000 description 2
• USSIQXCVUWKGNF-UHFFFAOYSA-N 6-(dimethylamino)-4,4-diphenylheptan-3-one Chemical compound C=1C=CC=CC=1C(CC(C)N(C)C)(C(=O)CC)C1=CC=CC=C1 USSIQXCVUWKGNF-UHFFFAOYSA-N 0.000 description 2
• 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 description 2
• 201000010000 Agranulocytosis Diseases 0.000 description 2
• 206010001540 Akathisia Diseases 0.000 description 2
• 101710195183 Alpha-bungarotoxin Proteins 0.000 description 2
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
• 208000000044 Amnesia Diseases 0.000 description 2
• 208000014644 Brain disease Diseases 0.000 description 2
• 108010009685 Cholinergic Receptors Proteins 0.000 description 2
• GJSURZIOUXUGAL-UHFFFAOYSA-N Clonidine Chemical compound ClC1=CC=CC(Cl)=C1NC1=NCCN1 GJSURZIOUXUGAL-UHFFFAOYSA-N 0.000 description 2
• 208000020401 Depressive disease Diseases 0.000 description 2
• 206010012735 Diarrhoea Diseases 0.000 description 2
• 208000012661 Dyskinesia Diseases 0.000 description 2
• YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
• 208000007882 Gastritis Diseases 0.000 description 2
• 208000018522 Gastrointestinal disease Diseases 0.000 description 2
• 201000004311 Gilles de la Tourette syndrome Diseases 0.000 description 2
• 206010019233 Headaches Diseases 0.000 description 2
• 241000282412 Homo Species 0.000 description 2
• 241000725303 Human immunodeficiency virus Species 0.000 description 2
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
• 208000006083 Hypokinesia Diseases 0.000 description 2
• 208000001953 Hypotension Diseases 0.000 description 2
• 208000015592 Involuntary movements Diseases 0.000 description 2
• 206010025421 Macule Diseases 0.000 description 2
• OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
• DUGOZIWVEXMGBE-UHFFFAOYSA-N Methylphenidate Chemical compound C=1C=CC=CC=1C(C(=O)OC)C1CCCCN1 DUGOZIWVEXMGBE-UHFFFAOYSA-N 0.000 description 2
• KLPWJLBORRMFGK-UHFFFAOYSA-N Molindone Chemical compound O=C1C=2C(CC)=C(C)NC=2CCC1CN1CCOCC1 KLPWJLBORRMFGK-UHFFFAOYSA-N 0.000 description 2
• 206010027951 Mood swings Diseases 0.000 description 2
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
• 206010052904 Musculoskeletal stiffness Diseases 0.000 description 2
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-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
• 206010028980 Neoplasm Diseases 0.000 description 2
• 208000012902 Nervous system disease Diseases 0.000 description 2
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
• MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 2
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
• 206010034719 Personality change Diseases 0.000 description 2
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
• 102000003946 Prolactin Human genes 0.000 description 2
• 108010057464 Prolactin Proteins 0.000 description 2
• 208000001431 Psychomotor Agitation Diseases 0.000 description 2
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
• PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
• 229920002472 Starch Polymers 0.000 description 2
• 208000007107 Stomach Ulcer Diseases 0.000 description 2
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
• KLBQZWRITKRQQV-UHFFFAOYSA-N Thioridazine Chemical compound C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C KLBQZWRITKRQQV-UHFFFAOYSA-N 0.000 description 2
• GFBKORZTTCHDGY-UWVJOHFNSA-N Thiothixene Chemical compound C12=CC(S(=O)(=O)N(C)C)=CC=C2SC2=CC=CC=C2\C1=C\CCN1CCN(C)CC1 GFBKORZTTCHDGY-UWVJOHFNSA-N 0.000 description 2
• ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
• 208000016620 Tourette disease Diseases 0.000 description 2
• 206010048010 Withdrawal syndrome Diseases 0.000 description 2
• SORGEQQSQGNZFI-UHFFFAOYSA-N [azido(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(N=[N+]=[N-])OC1=CC=CC=C1 SORGEQQSQGNZFI-UHFFFAOYSA-N 0.000 description 2
• 230000002159 abnormal effect Effects 0.000 description 2
• 150000007513 acids Chemical class 0.000 description 2
• 230000003213 activating effect Effects 0.000 description 2
• 230000001154 acute effect Effects 0.000 description 2
• WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
• 239000002671 adjuvant Substances 0.000 description 2
• 150000001413 amino acids Chemical class 0.000 description 2
• 239000000908 ammonium hydroxide Substances 0.000 description 2
• 239000002111 antiemetic agent Substances 0.000 description 2
• 239000003420 antiserotonin agent Substances 0.000 description 2
• 239000002249 anxiolytic agent Substances 0.000 description 2
• 238000013542 behavioral therapy Methods 0.000 description 2
• 229940049706 benzodiazepine Drugs 0.000 description 2
• 150000001557 benzodiazepines Chemical class 0.000 description 2
• 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
• YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 2
• 208000030963 borderline personality disease Diseases 0.000 description 2
• 244000309464 bull Species 0.000 description 2
• SNPPWIUOZRMYNY-UHFFFAOYSA-N bupropion Chemical compound CC(C)(C)NC(C)C(=O)C1=CC=CC(Cl)=C1 SNPPWIUOZRMYNY-UHFFFAOYSA-N 0.000 description 2
• RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 2
• 229920002678 cellulose Polymers 0.000 description 2
• 230000008859 change Effects 0.000 description 2
• 239000003153 chemical reaction reagent Substances 0.000 description 2
• 238000004296 chiral HPLC Methods 0.000 description 2
• IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
• 229960002896 clonidine Drugs 0.000 description 2
• ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 2
• 238000009225 cognitive behavioral therapy Methods 0.000 description 2
• 230000036461 convulsion Effects 0.000 description 2
• HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
• 230000006378 damage Effects 0.000 description 2
• 230000007812 deficiency Effects 0.000 description 2
• 230000018044 dehydration Effects 0.000 description 2
• 238000006297 dehydration reaction Methods 0.000 description 2
• 230000006866 deterioration Effects 0.000 description 2
• HBEDSQVIWPRPAY-UHFFFAOYSA-N dihydro-benzofuran Natural products C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 description 2
• 229940043279 diisopropylamine Drugs 0.000 description 2
• 239000006185 dispersion Substances 0.000 description 2
• VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
• 239000003596 drug target Substances 0.000 description 2
• 230000010482 emotional regulation Effects 0.000 description 2
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
• 239000006260 foam Substances 0.000 description 2
• 210000003918 fraction a Anatomy 0.000 description 2
• 239000001530 fumaric acid Substances 0.000 description 2
• AHIXHWRUDZFHEZ-UHFFFAOYSA-N furan-2,3-dicarbaldehyde Chemical compound O=CC=1C=COC=1C=O AHIXHWRUDZFHEZ-UHFFFAOYSA-N 0.000 description 2
• UUKNFBHTKFKPEH-UHFFFAOYSA-N furo[2,3-c]pyridin-5-ylmethanol Chemical compound C1=NC(CO)=CC2=C1OC=C2 UUKNFBHTKFKPEH-UHFFFAOYSA-N 0.000 description 2
• 229960003692 gamma aminobutyric acid Drugs 0.000 description 2
• 208000037870 generalized anxiety Diseases 0.000 description 2
• KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
• 208000035474 group of disease Diseases 0.000 description 2
• 229940093915 gynecological organic acid Drugs 0.000 description 2
• 229910052736 halogen Inorganic materials 0.000 description 2
• 150000002367 halogens Chemical class 0.000 description 2
• 229960003878 haloperidol Drugs 0.000 description 2
• 231100000869 headache Toxicity 0.000 description 2
• 230000036541 health Effects 0.000 description 2
• 238000010438 heat treatment Methods 0.000 description 2
• 238000007327 hydrogenolysis reaction Methods 0.000 description 2
• 230000003483 hypokinetic effect Effects 0.000 description 2
• 230000036543 hypotension Effects 0.000 description 2
• 230000001939 inductive effect Effects 0.000 description 2
• 239000003112 inhibitor Substances 0.000 description 2
• 208000014674 injury Diseases 0.000 description 2
• 150000007529 inorganic bases Chemical class 0.000 description 2
• 230000004410 intraocular pressure Effects 0.000 description 2
• 208000002551 irritable bowel syndrome Diseases 0.000 description 2
• XBMIVRRWGCYBTQ-AVRDEDQJSA-N levacetylmethadol Chemical compound C=1C=CC=CC=1C(C[C@H](C)N(C)C)([C@@H](OC(C)=O)CC)C1=CC=CC=C1 XBMIVRRWGCYBTQ-AVRDEDQJSA-N 0.000 description 2
• 230000007774 longterm Effects 0.000 description 2
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
• 230000006984 memory degeneration Effects 0.000 description 2
• 206010027175 memory impairment Diseases 0.000 description 2
• 208000023060 memory loss Diseases 0.000 description 2
• 230000003340 mental effect Effects 0.000 description 2
• 229960001797 methadone Drugs 0.000 description 2
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
• AXXXNDPZZKCHAH-QWHCGFSZSA-N methyl 2-[(3r)-1-[(1s)-1-phenylethyl]pyrrolidin-3-yl]acetate Chemical compound C1[C@@H](CC(=O)OC)CCN1[C@@H](C)C1=CC=CC=C1 AXXXNDPZZKCHAH-QWHCGFSZSA-N 0.000 description 2
• ZFCLYJSFOBGLFF-UHFFFAOYSA-N methyl furo[3,2-c]pyridine-6-carboxylate Chemical compound C1=NC(C(=O)OC)=CC2=C1C=CO2 ZFCLYJSFOBGLFF-UHFFFAOYSA-N 0.000 description 2
• 229960001344 methylphenidate Drugs 0.000 description 2
• 239000002480 mineral oil Substances 0.000 description 2
• 235000010446 mineral oil Nutrition 0.000 description 2
• 150000007522 mineralic acids Chemical class 0.000 description 2
• 230000004048 modification Effects 0.000 description 2
• 238000012986 modification Methods 0.000 description 2
• 229960004938 molindone Drugs 0.000 description 2
• 230000036651 mood Effects 0.000 description 2
• 210000003205 muscle Anatomy 0.000 description 2
• 230000017311 musculoskeletal movement, spinal reflex action Effects 0.000 description 2
• QLAJSAFFGXMIGO-UHFFFAOYSA-N n-(1-azabicyclo[2.2.1]heptan-3-yl)furo[2,3-b]pyridine-2-carboxamide Chemical compound C1=CN=C2OC(C(NC3C4CCN(C4)C3)=O)=CC2=C1 QLAJSAFFGXMIGO-UHFFFAOYSA-N 0.000 description 2
• PNKFNIMNXHHVAB-UHFFFAOYSA-N n-(1-azabicyclo[2.2.1]heptan-3-yl)thieno[2,3-b]pyridine-5-carboxamide Chemical compound N1=C2SC=CC2=CC(C(NC2C3CCN(C3)C2)=O)=C1 PNKFNIMNXHHVAB-UHFFFAOYSA-N 0.000 description 2
• ZBGGQJWUFSJRDO-UHFFFAOYSA-N n-(2-azabicyclo[2.2.1]heptan-5-yl)-3,3-dimethyl-2h-furo[2,3-c]pyridine-5-carboxamide Chemical compound C1=C2C(C)(C)COC2=CN=C1C(=O)NC1C(CN2)CC2C1 ZBGGQJWUFSJRDO-UHFFFAOYSA-N 0.000 description 2
• VJRHKWLZVFZTFX-ZYHUDNBSSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]thieno[2,3-b]pyridine-2-carboxamide Chemical compound C1=CN=C2SC(C(=O)N[C@H]3CN4CC[C@@](C4)(C3)[H])=CC2=C1 VJRHKWLZVFZTFX-ZYHUDNBSSA-N 0.000 description 2
• 210000000653 nervous system Anatomy 0.000 description 2
• 210000002569 neuron Anatomy 0.000 description 2
• 230000003557 neuropsychological effect Effects 0.000 description 2
• KVWDHTXUZHCGIO-UHFFFAOYSA-N olanzapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=C1C=C(C)S2 KVWDHTXUZHCGIO-UHFFFAOYSA-N 0.000 description 2
• 229960005343 ondansetron Drugs 0.000 description 2
• 230000003287 optical effect Effects 0.000 description 2
• 239000010502 orange oil Substances 0.000 description 2
• 150000007524 organic acids Chemical class 0.000 description 2
• 235000005985 organic acids Nutrition 0.000 description 2
• 150000007530 organic bases Chemical class 0.000 description 2
• 125000002524 organometallic group Chemical group 0.000 description 2
• 229910052763 palladium Inorganic materials 0.000 description 2
• NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 2
• 230000037361 pathway Effects 0.000 description 2
• 230000002085 persistent effect Effects 0.000 description 2
• YVUQSNJEYSNKRX-UHFFFAOYSA-N pimozide Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)CCCN1CCC(N2C(NC3=CC=CC=C32)=O)CC1 YVUQSNJEYSNKRX-UHFFFAOYSA-N 0.000 description 2
• 229960003634 pimozide Drugs 0.000 description 2
• 150000003053 piperidines Chemical class 0.000 description 2
• TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
• 230000003389 potentiating effect Effects 0.000 description 2
• 244000144977 poultry Species 0.000 description 2
• 229940097325 prolactin Drugs 0.000 description 2
• 235000019260 propionic acid Nutrition 0.000 description 2
• 238000000159 protein binding assay Methods 0.000 description 2
• 230000005180 public health Effects 0.000 description 2
• 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 2
• 125000005493 quinolyl group Chemical group 0.000 description 2
• 150000008584 quinuclidines Chemical class 0.000 description 2
• 230000005855 radiation Effects 0.000 description 2
• RAPZEAPATHNIPO-UHFFFAOYSA-N risperidone Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCCC4=NC=3C)=NOC2=C1 RAPZEAPATHNIPO-UHFFFAOYSA-N 0.000 description 2
• AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
• 235000019345 sodium thiosulphate Nutrition 0.000 description 2
• 238000001228 spectrum Methods 0.000 description 2
• 208000027765 speech disease Diseases 0.000 description 2
• 238000010561 standard procedure Methods 0.000 description 2
• 239000008107 starch Substances 0.000 description 2
• 235000019698 starch Nutrition 0.000 description 2
• 238000003756 stirring Methods 0.000 description 2
• 239000012730 sustained-release form Substances 0.000 description 2
• 238000012360 testing method Methods 0.000 description 2
• YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 description 2
• 230000001225 therapeutic effect Effects 0.000 description 2
• ZBWCOZDGHJCGSC-UHFFFAOYSA-N thieno[3,2-b]pyridine-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=N1 ZBWCOZDGHJCGSC-UHFFFAOYSA-N 0.000 description 2
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
• ZEWQUBUPAILYHI-UHFFFAOYSA-N trifluoperazine Chemical compound C1CN(C)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 ZEWQUBUPAILYHI-UHFFFAOYSA-N 0.000 description 2
• GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
• 230000008673 vomiting Effects 0.000 description 2
• JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
• MVWVFYHBGMAFLY-UHFFFAOYSA-N ziprasidone Chemical compound C1=CC=C2C(N3CCN(CC3)CCC3=CC=4CC(=O)NC=4C=C3Cl)=NSC2=C1 MVWVFYHBGMAFLY-UHFFFAOYSA-N 0.000 description 2
• 229940018503 zyban Drugs 0.000 description 2
• LYTCVQQGCSNFJU-LKGYBJPKSA-N α-bungarotoxin Chemical compound C(/[C@H]1O[C@H]2C[C@H]3O[C@@H](CC(=C)C=O)C[C@H](O)[C@]3(C)O[C@@H]2C[C@@H]1O[C@@H]1C2)=C/C[C@]1(C)O[C@H]1[C@@]2(C)O[C@]2(C)CC[C@@H]3O[C@@H]4C[C@]5(C)O[C@@H]6C(C)=CC(=O)O[C@H]6C[C@H]5O[C@H]4C[C@@H](C)[C@H]3O[C@H]2C1 LYTCVQQGCSNFJU-LKGYBJPKSA-N 0.000 description 2
• AHOUBRCZNHFOSL-YOEHRIQHSA-N (+)-Casbol Chemical compound C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-YOEHRIQHSA-N 0.000 description 1
• OGNSCSPNOLGXSM-UHFFFAOYSA-N (+/-)-DABA Natural products NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 description 1
• TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
• RQEUFEKYXDPUSK-ZETCQYMHSA-N (1S)-1-phenylethanamine Chemical compound C[C@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-ZETCQYMHSA-N 0.000 description 1
• GLJCSEMYUCHNJA-GPJOBVNKSA-N (3r,5r)-1-azabicyclo[3.2.1]octan-3-amine;dihydrochloride Chemical compound Cl.Cl.C1N2CC[C@]1([H])C[C@@H](N)C2 GLJCSEMYUCHNJA-GPJOBVNKSA-N 0.000 description 1
• IFARNTRSDZVQOX-NWDGAFQWSA-N (3s)-3-(chloromethyl)-1-[(1s)-1-phenylethyl]pyrrolidine Chemical compound N1([C@@H](C)C=2C=CC=CC=2)CC[C@H](CCl)C1 IFARNTRSDZVQOX-NWDGAFQWSA-N 0.000 description 1
• CFGKWSDAMXTRHE-ONGXEEELSA-N (3s)-5-oxo-1-[(1s)-1-phenylethyl]pyrrolidine-3-carboxylic acid Chemical compound N1([C@@H](C)C=2C=CC=CC=2)C[C@@H](C(O)=O)CC1=O CFGKWSDAMXTRHE-ONGXEEELSA-N 0.000 description 1
• DIWRORZWFLOCLC-HNNXBMFYSA-N (3s)-7-chloro-5-(2-chlorophenyl)-3-hydroxy-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound N([C@H](C(NC1=CC=C(Cl)C=C11)=O)O)=C1C1=CC=CC=C1Cl DIWRORZWFLOCLC-HNNXBMFYSA-N 0.000 description 1
• NMBYTCZMEUZKSJ-FTLRAWMYSA-N (5r)-1-[(1s)-1-phenylethyl]-1-azoniabicyclo[3.2.1]octan-3-one Chemical compound C1([C@H](C)[N+]23C[C@H](CC2)CC(=O)C3)=CC=CC=C1 NMBYTCZMEUZKSJ-FTLRAWMYSA-N 0.000 description 1
• IIPJFASIZVDONL-UHFFFAOYSA-N (7-chloro-2-trimethylsilylfuro[2,3-c]pyridin-5-yl)methanol Chemical compound OCC1=NC(Cl)=C2OC([Si](C)(C)C)=CC2=C1 IIPJFASIZVDONL-UHFFFAOYSA-N 0.000 description 1
• WSEQXVZVJXJVFP-HXUWFJFHSA-N (R)-citalopram Chemical compound C1([C@@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-HXUWFJFHSA-N 0.000 description 1
• RTHCYVBBDHJXIQ-MRXNPFEDSA-N (R)-fluoxetine Chemical compound O([C@H](CCNC)C=1C=CC=CC=1)C1=CC=C(C(F)(F)F)C=C1 RTHCYVBBDHJXIQ-MRXNPFEDSA-N 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
• DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
• NNFCZWMIDCZWBX-UHFFFAOYSA-N 1,2-benzoxazepine-3-carboxamide Chemical class C1=CC(C(=O)N)=NOC2=CC=CC=C21 NNFCZWMIDCZWBX-UHFFFAOYSA-N 0.000 description 1
• NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
• UMQPWGSSJHTJBH-UHFFFAOYSA-N 1-(1h-imidazol-2-yl)-9h-carbazole Chemical compound C1=CNC(C=2C=3NC4=CC=CC=C4C=3C=CC=2)=N1 UMQPWGSSJHTJBH-UHFFFAOYSA-N 0.000 description 1
• PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
• FEWLNYSYJNLUOO-UHFFFAOYSA-N 1-Piperidinecarboxaldehyde Chemical compound O=CN1CCCCC1 FEWLNYSYJNLUOO-UHFFFAOYSA-N 0.000 description 1
• UALFYMMGEYDHHJ-UHFFFAOYSA-N 1-azabicyclo[3.2.2]nonan-3-amine Chemical compound C1C(N)CC2CCN1CC2 UALFYMMGEYDHHJ-UHFFFAOYSA-N 0.000 description 1
• WOVRTYYYRIRFPW-UHFFFAOYSA-N 1-azabicyclo[3.2.2]nonan-3-amine;4-methylbenzenesulfonic acid Chemical compound C1C(N)CC2CCN1CC2.CC1=CC=C(S(O)(=O)=O)C=C1.CC1=CC=C(S(O)(=O)=O)C=C1 WOVRTYYYRIRFPW-UHFFFAOYSA-N 0.000 description 1
• RASGVORPWAYILQ-UHFFFAOYSA-N 1-azabicyclo[3.2.2]nonane Chemical class C1CC2CCN1CCC2 RASGVORPWAYILQ-UHFFFAOYSA-N 0.000 description 1
• OFFSPAZVIVZPHU-UHFFFAOYSA-N 1-benzofuran-2-carboxylic acid Chemical class C1=CC=C2OC(C(=O)O)=CC2=C1 OFFSPAZVIVZPHU-UHFFFAOYSA-N 0.000 description 1
• RUJGCPIIPXGIHS-UHFFFAOYSA-N 1-bromo-3-piperidin-4-ylpropan-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.BrCC(=O)CC1CCNCC1 RUJGCPIIPXGIHS-UHFFFAOYSA-N 0.000 description 1
• JKXQKGNGJVZKFA-UHFFFAOYSA-N 1-chloro-3-methylbut-2-ene Chemical compound CC(C)=CCCl JKXQKGNGJVZKFA-UHFFFAOYSA-N 0.000 description 1
• RSAFKRSMGOSHRK-UHFFFAOYSA-N 1-diethoxyphosphorylpropan-2-one Chemical compound CCOP(=O)(CC(C)=O)OCC RSAFKRSMGOSHRK-UHFFFAOYSA-N 0.000 description 1
• IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
• RHXSYTACTOMVLJ-UHFFFAOYSA-N 1H-benzimidazole-2-carboxylic acid Chemical class C1=CC=C2NC(C(=O)O)=NC2=C1 RHXSYTACTOMVLJ-UHFFFAOYSA-N 0.000 description 1
• ZNRGQMMCGHDTEI-UHFFFAOYSA-N 1H-indole-3-carboxylic acid (8-methyl-8-azabicyclo[3.2.1]octan-3-yl) ester Chemical compound C1=CC=C2C(C(=O)OC3CC4CCC(C3)N4C)=CNC2=C1 ZNRGQMMCGHDTEI-UHFFFAOYSA-N 0.000 description 1
• GVVIAZOBDFNZPB-UHFFFAOYSA-N 1h-1-benzazepine-2-carboxamide Chemical class N1C(C(=O)N)=CC=CC2=CC=CC=C21 GVVIAZOBDFNZPB-UHFFFAOYSA-N 0.000 description 1
• JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
• MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
• IAXKDYYTMWUUIA-UHFFFAOYSA-N 2-azabicyclo[2.2.1]heptan-5-amine Chemical compound C1C2C(N)CC1NC2 IAXKDYYTMWUUIA-UHFFFAOYSA-N 0.000 description 1
• RSOPTYAZDFSMTN-UHFFFAOYSA-N 2-chloropyridin-3-ol Chemical compound OC1=CC=CN=C1Cl RSOPTYAZDFSMTN-UHFFFAOYSA-N 0.000 description 1
• OKDGRDCXVWSXDC-UHFFFAOYSA-N 2-chloropyridine Chemical compound ClC1=CC=CC=N1 OKDGRDCXVWSXDC-UHFFFAOYSA-N 0.000 description 1
• BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
• 229940013085 2-diethylaminoethanol Drugs 0.000 description 1
• HGMKWFMIOFOYOX-UHFFFAOYSA-N 2-formyl-3-methylbutanenitrile;sodium Chemical compound [Na].CC(C)C(C=O)C#N HGMKWFMIOFOYOX-UHFFFAOYSA-N 0.000 description 1
• LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
• CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 description 1
• RETCYVKOCFWWTL-UHFFFAOYSA-N 3-(2-aminoethyl)-1h-indol-7-ol Chemical compound C1=CC=C2C(CCN)=CNC2=C1O RETCYVKOCFWWTL-UHFFFAOYSA-N 0.000 description 1
• KLDLRDSRCMJKGM-UHFFFAOYSA-N 3-[chloro-(2-oxo-1,3-oxazolidin-3-yl)phosphoryl]-1,3-oxazolidin-2-one Chemical compound C1COC(=O)N1P(=O)(Cl)N1CCOC1=O KLDLRDSRCMJKGM-UHFFFAOYSA-N 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
• USEGQJLHQSTGHW-UHFFFAOYSA-N 3-bromo-2-methylprop-1-ene Chemical compound CC(=C)CBr USEGQJLHQSTGHW-UHFFFAOYSA-N 0.000 description 1
• LXWLEQZDXOQZGW-UHFFFAOYSA-N 3-bromofuran Chemical compound BrC=1C=COC=1 LXWLEQZDXOQZGW-UHFFFAOYSA-N 0.000 description 1
• PWRBCZZQRRPXAB-UHFFFAOYSA-N 3-chloropyridine Chemical compound ClC1=CC=CN=C1 PWRBCZZQRRPXAB-UHFFFAOYSA-N 0.000 description 1
• IVLICPVPXWEGCA-UHFFFAOYSA-N 3-quinuclidinol Chemical class C1C[C@@H]2C(O)C[N@]1CC2 IVLICPVPXWEGCA-UHFFFAOYSA-N 0.000 description 1
• 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 1
• OLJXRTRRJSMURJ-UHFFFAOYSA-N 4-amino-2-methoxybenzoic acid Chemical class COC1=CC(N)=CC=C1C(O)=O OLJXRTRRJSMURJ-UHFFFAOYSA-N 0.000 description 1
• 229940127239 5 Hydroxytryptamine receptor antagonist Drugs 0.000 description 1
• 108091005477 5-HT3 receptors Proteins 0.000 description 1
• 108091005482 5-HT4 receptors Proteins 0.000 description 1
• SDRZCVDIDNFMAD-UHFFFAOYSA-N 7-oxidothieno[2,3-b]pyridin-7-ium Chemical compound [O-][N+]1=CC=CC2=C1SC=C2 SDRZCVDIDNFMAD-UHFFFAOYSA-N 0.000 description 1
• 208000004998 Abdominal Pain Diseases 0.000 description 1
• 206010000060 Abdominal distension Diseases 0.000 description 1
• 206010001497 Agitation Diseases 0.000 description 1
• GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
• 206010002650 Anorexia nervosa and bulimia Diseases 0.000 description 1
• 239000004475 Arginine Substances 0.000 description 1
• 241000271566 Aves Species 0.000 description 1
• 208000008035 Back Pain Diseases 0.000 description 1
• FJCWELGHBURNRJ-DGGCSGMNSA-N C(\C=C\C(=O)O)(=O)O.O1C=CC=2C1=CN=C(C2)C(=O)N[C@@H]2CN1CCC2C1 Chemical compound C(\C=C\C(=O)O)(=O)O.O1C=CC=2C1=CN=C(C2)C(=O)N[C@@H]2CN1CCC2C1 FJCWELGHBURNRJ-DGGCSGMNSA-N 0.000 description 1
• KCBAMQOKOLXLOX-BSZYMOERSA-N CC1=C(SC=N1)C2=CC=C(C=C2)[C@H](C)NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@H](C(C)(C)C)NC(=O)CCCCCCCCCCNCCCONC(=O)C4=C(C(=C(C=C4)F)F)NC5=C(C=C(C=C5)I)F)O Chemical compound CC1=C(SC=N1)C2=CC=C(C=C2)[C@H](C)NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@H](C(C)(C)C)NC(=O)CCCCCCCCCCNCCCONC(=O)C4=C(C(=C(C=C4)F)F)NC5=C(C=C(C=C5)I)F)O KCBAMQOKOLXLOX-BSZYMOERSA-N 0.000 description 1
• 108090000312 Calcium Channels Proteins 0.000 description 1
• 102000003922 Calcium Channels Human genes 0.000 description 1
• BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
• 244000025254 Cannabis sativa Species 0.000 description 1
• 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
• 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
• 239000004215 Carbon black (E152) Substances 0.000 description 1
• 206010007270 Carcinoid syndrome Diseases 0.000 description 1
• 102000000844 Cell Surface Receptors Human genes 0.000 description 1
• 108010001857 Cell Surface Receptors Proteins 0.000 description 1
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
• 206010008748 Chorea Diseases 0.000 description 1
• 208000028698 Cognitive impairment Diseases 0.000 description 1
• 206010009900 Colitis ulcerative Diseases 0.000 description 1
• 206010010964 Coprolalia Diseases 0.000 description 1
• 208000011231 Crohn disease Diseases 0.000 description 1
• 206010012218 Delirium Diseases 0.000 description 1
• 208000031124 Dementia Alzheimer type 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
• YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 1
• 229940121891 Dopamine receptor antagonist Drugs 0.000 description 1
• 206010013954 Dysphoria Diseases 0.000 description 1
• 208000014094 Dystonic disease Diseases 0.000 description 1
• 208000030814 Eating disease Diseases 0.000 description 1
• 208000030644 Esophageal Motility disease Diseases 0.000 description 1
• 241001539473 Euphoria Species 0.000 description 1
• 206010015535 Euphoric mood Diseases 0.000 description 1
• CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
• 208000019454 Feeding and Eating disease Diseases 0.000 description 1
• 208000001640 Fibromyalgia Diseases 0.000 description 1
• 208000001613 Gambling Diseases 0.000 description 1
• 208000012895 Gastric disease Diseases 0.000 description 1
• 208000017228 Gastrointestinal motility disease Diseases 0.000 description 1
• 206010018045 Gastroptosis Diseases 0.000 description 1
• 108010010803 Gelatin Chemical class 0.000 description 1
• 108700039691 Genetic Promoter Regions Proteins 0.000 description 1
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
• 102000011714 Glycine Receptors Human genes 0.000 description 1
• 108010076533 Glycine Receptors Proteins 0.000 description 1
• 208000031886 HIV Infections Diseases 0.000 description 1
• 208000037357 HIV infectious disease Diseases 0.000 description 1
• 206010019280 Heart failures Diseases 0.000 description 1
• GVGLGOZIDCSQPN-PVHGPHFFSA-N Heroin Chemical compound O([C@H]1[C@H](C=C[C@H]23)OC(C)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4OC(C)=O GVGLGOZIDCSQPN-PVHGPHFFSA-N 0.000 description 1
• 238000004566 IR spectroscopy Methods 0.000 description 1
• 206010021333 Ileus paralytic Diseases 0.000 description 1
• 201000005081 Intestinal Pseudo-Obstruction Diseases 0.000 description 1
• LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 1
• ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
• HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 1
• KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
• 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
• 240000007472 Leucaena leucocephala Species 0.000 description 1
• 239000004472 Lysine Substances 0.000 description 1
• KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
• WSMYVTOQOOLQHP-UHFFFAOYSA-N Malondialdehyde Chemical compound O=CCC=O WSMYVTOQOOLQHP-UHFFFAOYSA-N 0.000 description 1
• 206010027374 Mental impairment Diseases 0.000 description 1
• 241001465754 Metazoa Species 0.000 description 1
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
• 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
• 238000006751 Mitsunobu reaction Methods 0.000 description 1
• 208000001089 Multiple system atrophy Diseases 0.000 description 1
• 241001529936 Murinae Species 0.000 description 1
• 101100348848 Mus musculus Notch4 gene Proteins 0.000 description 1
• 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 description 1
• 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 description 1
• 206010049816 Muscle tightness Diseases 0.000 description 1
• 208000002033 Myoclonus Diseases 0.000 description 1
• HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 1
• STJZWEQHOMJRNQ-MWLCHTKSSA-N N-[(3R,5R)-1-azabicyclo[3.2.1]octan-3-yl]-2-sulfanylfuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC(S)=C2 STJZWEQHOMJRNQ-MWLCHTKSSA-N 0.000 description 1
• UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
• HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
• MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
• 208000018526 Narcotic-Related disease Diseases 0.000 description 1
• 208000009668 Neurobehavioral Manifestations Diseases 0.000 description 1
• 206010029333 Neurosis Diseases 0.000 description 1
• 206010057852 Nicotine dependence Diseases 0.000 description 1
• 102100029438 Nitric oxide synthase, inducible Human genes 0.000 description 1
• 101710089543 Nitric oxide synthase, inducible Proteins 0.000 description 1
• 235000019502 Orange oil Nutrition 0.000 description 1
• 206010031127 Orthostatic hypotension Diseases 0.000 description 1
• 229930040373 Paraformaldehyde Natural products 0.000 description 1
• 208000027089 Parkinsonian disease Diseases 0.000 description 1
• 206010034010 Parkinsonism Diseases 0.000 description 1
• AHOUBRCZNHFOSL-UHFFFAOYSA-N Paroxetine hydrochloride Natural products C1=CC(F)=CC=C1C1C(COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-UHFFFAOYSA-N 0.000 description 1
• 235000019483 Peanut oil Nutrition 0.000 description 1
• RGCVKNLCSQQDEP-UHFFFAOYSA-N Perphenazine Chemical compound C1CN(CCO)CCN1CCCN1C2=CC(Cl)=CC=C2SC2=CC=CC=C21 RGCVKNLCSQQDEP-UHFFFAOYSA-N 0.000 description 1
• 206010034912 Phobia Diseases 0.000 description 1
• 239000002202 Polyethylene glycol Substances 0.000 description 1
• 208000004880 Polyuria Diseases 0.000 description 1
• 239000004372 Polyvinyl alcohol Substances 0.000 description 1
• 102000004257 Potassium Channel Human genes 0.000 description 1
• ZGUGWUXLJSTTMA-UHFFFAOYSA-N Promazinum Chemical compound C1=CC=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZGUGWUXLJSTTMA-UHFFFAOYSA-N 0.000 description 1
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
• 206010038743 Restlessness Diseases 0.000 description 1
• FTALBRSUTCGOEG-UHFFFAOYSA-N Riluzole Chemical compound C1=C(OC(F)(F)F)C=C2SC(N)=NC2=C1 FTALBRSUTCGOEG-UHFFFAOYSA-N 0.000 description 1
• 241000283984 Rodentia Species 0.000 description 1
• 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 1
• 101000650578 Salmonella phage P22 Regulatory protein C3 Proteins 0.000 description 1
• 206010040030 Sensory loss Diseases 0.000 description 1
• 229910004298 SiO 2 Inorganic materials 0.000 description 1
• 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 1
• 208000032140 Sleepiness Diseases 0.000 description 1
• 108010052164 Sodium Channels Proteins 0.000 description 1
• 102000018674 Sodium Channels Human genes 0.000 description 1
• 239000004280 Sodium formate Substances 0.000 description 1
• 206010041349 Somnolence Diseases 0.000 description 1
• 235000021355 Stearic acid Nutrition 0.000 description 1
• 208000013200 Stress disease Diseases 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
• 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 1
• 229930006000 Sucrose Natural products 0.000 description 1
• 208000001871 Tachycardia 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
• 208000008234 Tics Diseases 0.000 description 1
• 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
• 208000025569 Tobacco Use disease Diseases 0.000 description 1
• 229940123445 Tricyclic antidepressant Drugs 0.000 description 1
• 101001040920 Triticum aestivum Alpha-amylase inhibitor 0.28 Proteins 0.000 description 1
• 201000006704 Ulcerative Colitis Diseases 0.000 description 1
• 241000700605 Viruses Species 0.000 description 1
• 208000027418 Wounds and injury Diseases 0.000 description 1
• 241000269370 Xenopus <genus> Species 0.000 description 1
• RQTYGPRJDFTUGU-RYUDHWBXSA-N [(3s)-1-[(1s)-1-phenylethyl]pyrrolidin-3-yl]methanol Chemical compound N1([C@@H](C)C=2C=CC=CC=2)CC[C@H](CO)C1 RQTYGPRJDFTUGU-RYUDHWBXSA-N 0.000 description 1
• 206010000059 abdominal discomfort Diseases 0.000 description 1
• 238000010521 absorption reaction Methods 0.000 description 1
• ILLGYRJAYAAAEW-QMMMGPOBSA-N abt-418 Chemical compound CN1CCC[C@H]1C1=CC(C)=NO1 ILLGYRJAYAAAEW-QMMMGPOBSA-N 0.000 description 1
• WNTYBHLDCKXEOT-UHFFFAOYSA-N acetophenazine Chemical compound C12=CC(C(=O)C)=CC=C2SC2=CC=CC=C2N1CCCN1CCN(CCO)CC1 WNTYBHLDCKXEOT-UHFFFAOYSA-N 0.000 description 1
• 229960000276 acetophenazine Drugs 0.000 description 1
• WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
• 239000012346 acetyl chloride Substances 0.000 description 1
• 108020000715 acetylcholine receptors Proteins 0.000 description 1
• 230000004913 activation Effects 0.000 description 1
• 239000008186 active pharmaceutical agent Substances 0.000 description 1
• 239000013543 active substance Substances 0.000 description 1
• 125000004423 acyloxy group Chemical group 0.000 description 1
• 239000001361 adipic acid Substances 0.000 description 1
• 235000011037 adipic acid Nutrition 0.000 description 1
• 230000016571 aggressive behavior Effects 0.000 description 1
• 230000036626 alertness Effects 0.000 description 1
• 150000001335 aliphatic alkanes Chemical class 0.000 description 1
• 125000005907 alkyl ester group Chemical group 0.000 description 1
• 239000002168 alkylating agent Substances 0.000 description 1
• 229940100198 alkylating agent Drugs 0.000 description 1
• 230000029936 alkylation Effects 0.000 description 1
• 238000005804 alkylation reaction Methods 0.000 description 1
• BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
• AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
• 150000003863 ammonium salts Chemical class 0.000 description 1
• 238000004458 analytical method Methods 0.000 description 1
• 230000000954 anitussive effect Effects 0.000 description 1
• 230000002460 anti-migrenic effect Effects 0.000 description 1
• 229940124604 anti-psychotic medication Drugs 0.000 description 1
• 230000002738 anti-smoking effect Effects 0.000 description 1
• 239000003416 antiarrhythmic agent Substances 0.000 description 1
• 229940125683 antiemetic agent Drugs 0.000 description 1
• 229940082988 antihypertensives serotonin antagonists Drugs 0.000 description 1
• 239000002282 antimigraine agent Substances 0.000 description 1
• 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
• 229940054051 antipsychotic indole derivative Drugs 0.000 description 1
• 229940124584 antitussives Drugs 0.000 description 1
• 230000000949 anxiolytic effect Effects 0.000 description 1
• 229940005530 anxiolytics Drugs 0.000 description 1
• ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
• 229960003121 arginine Drugs 0.000 description 1
• 206010003119 arrhythmia Diseases 0.000 description 1
• 206010003246 arthritis Diseases 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
• 230000001174 ascending effect Effects 0.000 description 1
• 239000012298 atmosphere Substances 0.000 description 1
• 208000015802 attention deficit-hyperactivity disease Diseases 0.000 description 1
• MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 1
• HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 1
• 150000001540 azides Chemical class 0.000 description 1
• 210000004227 basal ganglia Anatomy 0.000 description 1
• 230000006399 behavior Effects 0.000 description 1
• 150000001556 benzimidazoles Chemical class 0.000 description 1
• 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
• SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
• MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 1
• WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
• 229960003237 betaine Drugs 0.000 description 1
• 125000002527 bicyclic carbocyclic group Chemical group 0.000 description 1
• 239000011230 binding agent Substances 0.000 description 1
• 239000003124 biologic agent Substances 0.000 description 1
• 208000028683 bipolar I disease Diseases 0.000 description 1
• 210000004204 blood vessel Anatomy 0.000 description 1
• 230000036471 bradycardia Effects 0.000 description 1
• 208000006218 bradycardia Diseases 0.000 description 1
• 230000003925 brain function Effects 0.000 description 1
• 229940045348 brown mixture Drugs 0.000 description 1
• 239000000872 buffer Substances 0.000 description 1
• QWCRAEMEVRGPNT-UHFFFAOYSA-N buspirone Chemical compound C1C(=O)N(CCCCN2CCN(CC2)C=2N=CC=CN=2)C(=O)CC21CCCC2 QWCRAEMEVRGPNT-UHFFFAOYSA-N 0.000 description 1
• 229960002495 buspirone Drugs 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
• 210000004899 c-terminal region Anatomy 0.000 description 1
• 229960001948 caffeine Drugs 0.000 description 1
• VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 1
• 229910001424 calcium ion Inorganic materials 0.000 description 1
• 159000000007 calcium salts Chemical class 0.000 description 1
• 201000011510 cancer Diseases 0.000 description 1
• 239000004202 carbamide Substances 0.000 description 1
• 150000001718 carbodiimides Chemical class 0.000 description 1
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
• XZSMZRXAEFNJCU-UHFFFAOYSA-N carfenazine Chemical compound C12=CC(C(=O)CC)=CC=C2SC2=CC=CC=C2N1CCCN1CCN(CCO)CC1 XZSMZRXAEFNJCU-UHFFFAOYSA-N 0.000 description 1
• 229950009852 carfenazine Drugs 0.000 description 1
• 230000015556 catabolic process Effects 0.000 description 1
• 239000001913 cellulose Substances 0.000 description 1
• 208000015114 central nervous system disease Diseases 0.000 description 1
• 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 description 1
• KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
• 238000002512 chemotherapy Methods 0.000 description 1
• 229940112822 chewing gum Drugs 0.000 description 1
• 108700010039 chimeric receptor Proteins 0.000 description 1
• 150000001805 chlorine compounds Chemical class 0.000 description 1
• 125000001309 chloro group Chemical group Cl* 0.000 description 1
• PJGJQVRXEUVAFT-UHFFFAOYSA-N chloroiodomethane Chemical compound ClCI PJGJQVRXEUVAFT-UHFFFAOYSA-N 0.000 description 1
• ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 description 1
• 229960001076 chlorpromazine Drugs 0.000 description 1
• OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
• 229960001231 choline Drugs 0.000 description 1
• 239000000544 cholinesterase inhibitor Substances 0.000 description 1
• 208000012601 choreatic disease Diseases 0.000 description 1
• 210000000349 chromosome Anatomy 0.000 description 1
• 230000001684 chronic effect Effects 0.000 description 1
• 208000023652 chronic gastritis Diseases 0.000 description 1
• 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
• 229960001653 citalopram Drugs 0.000 description 1
• 229960003120 clonazepam Drugs 0.000 description 1
• DGBIGWXXNGSACT-UHFFFAOYSA-N clonazepam Chemical compound C12=CC([N+](=O)[O-])=CC=C2NC(=O)CN=C1C1=CC=CC=C1Cl DGBIGWXXNGSACT-UHFFFAOYSA-N 0.000 description 1
• 238000011260 co-administration Methods 0.000 description 1
• 229960003920 cocaine Drugs 0.000 description 1
• 238000009226 cognitive therapy Methods 0.000 description 1
• 239000003086 colorant Substances 0.000 description 1
• 238000004040 coloring Methods 0.000 description 1
• 238000004440 column chromatography Methods 0.000 description 1
• 239000002285 corn oil Substances 0.000 description 1
• 235000005687 corn oil Nutrition 0.000 description 1
• 235000012343 cottonseed oil Nutrition 0.000 description 1
• 239000002385 cottonseed oil Substances 0.000 description 1
• 150000001907 coumarones Chemical class 0.000 description 1
• 229940051068 counteract pain Drugs 0.000 description 1
• YTKRILODNOEEPX-NSCUHMNNSA-N crotyl chloride Chemical compound C\C=C\CCl YTKRILODNOEEPX-NSCUHMNNSA-N 0.000 description 1
• 230000007423 decrease Effects 0.000 description 1
• 230000003247 decreasing effect Effects 0.000 description 1
• 230000007547 defect Effects 0.000 description 1
• 230000007850 degeneration Effects 0.000 description 1
• 238000012217 deletion Methods 0.000 description 1
• 230000037430 deletion Effects 0.000 description 1
• 238000010511 deprotection reaction Methods 0.000 description 1
• 238000000586 desensitisation Methods 0.000 description 1
• 239000002274 desiccant Substances 0.000 description 1
• 229960000632 dexamfetamine Drugs 0.000 description 1
• 239000008121 dextrose Substances 0.000 description 1
• 206010012601 diabetes mellitus Diseases 0.000 description 1
• 229960002069 diamorphine Drugs 0.000 description 1
• 229960003529 diazepam Drugs 0.000 description 1
• AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 1
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
• PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 description 1
• MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 1
• 239000007884 disintegrant Substances 0.000 description 1
• 235000014632 disordered eating Nutrition 0.000 description 1
• 208000002173 dizziness Diseases 0.000 description 1
• 229960003638 dopamine Drugs 0.000 description 1
• 239000003210 dopamine receptor blocking agent Substances 0.000 description 1
• 229940088679 drug related substance Drugs 0.000 description 1
• 208000000718 duodenal ulcer Diseases 0.000 description 1
• 230000004064 dysfunction Effects 0.000 description 1
• 201000006549 dyspepsia Diseases 0.000 description 1
• 208000010118 dystonia Diseases 0.000 description 1
• 235000005686 eating Nutrition 0.000 description 1
• 238000000132 electrospray ionisation Methods 0.000 description 1
• 238000010828 elution Methods 0.000 description 1
• 230000008451 emotion Effects 0.000 description 1
• 230000002996 emotional effect Effects 0.000 description 1
• 239000003623 enhancer Substances 0.000 description 1
• 230000001667 episodic effect Effects 0.000 description 1
• NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
• PMIMPBYTPPRBGD-UHFFFAOYSA-N ethyl 2-chloropyridine-3-carboxylate Chemical compound CCOC(=O)C1=CC=CN=C1Cl PMIMPBYTPPRBGD-UHFFFAOYSA-N 0.000 description 1
• ZANNOFHADGWOLI-UHFFFAOYSA-N ethyl 2-hydroxyacetate Chemical compound CCOC(=O)CO ZANNOFHADGWOLI-UHFFFAOYSA-N 0.000 description 1
• PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 1
• 231100000318 excitotoxic Toxicity 0.000 description 1
• 230000003492 excitotoxic effect Effects 0.000 description 1
• 238000002474 experimental method Methods 0.000 description 1
• 208000030533 eye disease Diseases 0.000 description 1
• 239000000796 flavoring agent Substances 0.000 description 1
• 125000001153 fluoro group Chemical group F* 0.000 description 1
• 229960002464 fluoxetine Drugs 0.000 description 1
• 229960004038 fluvoxamine Drugs 0.000 description 1
• CJOFXWAVKWHTFT-XSFVSMFZSA-N fluvoxamine Chemical compound COCCCC\C(=N/OCCN)C1=CC=C(C(F)(F)F)C=C1 CJOFXWAVKWHTFT-XSFVSMFZSA-N 0.000 description 1
• 235000013355 food flavoring agent Nutrition 0.000 description 1
• 235000019253 formic acid Nutrition 0.000 description 1
• WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
• 210000000540 fraction c Anatomy 0.000 description 1
• 239000003205 fragrance Substances 0.000 description 1
• 235000011087 fumaric acid Nutrition 0.000 description 1
• 238000007306 functionalization reaction Methods 0.000 description 1
• 125000003838 furazanyl group Chemical group 0.000 description 1
• KEMHDISEJAEDNP-UHFFFAOYSA-N furo[3,2-c]pyridine-6-carboxylic acid Chemical compound C1=NC(C(=O)O)=CC2=C1C=CO2 KEMHDISEJAEDNP-UHFFFAOYSA-N 0.000 description 1
• 125000004612 furopyridinyl group Chemical group O1C(=CC2=C1C=CC=N2)* 0.000 description 1
• 125000002541 furyl group Chemical group 0.000 description 1
• 208000020694 gallbladder disease Diseases 0.000 description 1
• 230000030136 gastric emptying Effects 0.000 description 1
• 230000030135 gastric motility Effects 0.000 description 1
• 208000021302 gastroesophageal reflux disease Diseases 0.000 description 1
• 239000008273 gelatin Chemical class 0.000 description 1
• 229920000159 gelatin Chemical class 0.000 description 1
• 235000019322 gelatine Nutrition 0.000 description 1
• 235000011852 gelatine desserts Nutrition 0.000 description 1
• 229960002442 glucosamine Drugs 0.000 description 1
• PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
• 229910052737 gold Inorganic materials 0.000 description 1
• 239000010931 gold Substances 0.000 description 1
• 239000008187 granular material Substances 0.000 description 1
• 229940095895 haldol Drugs 0.000 description 1
• 239000000380 hallucinogen Substances 0.000 description 1
• 125000001188 haloalkyl group Chemical group 0.000 description 1
• 210000003128 head Anatomy 0.000 description 1
• 231100000206 health hazard Toxicity 0.000 description 1
• 208000024798 heartburn Diseases 0.000 description 1
• 150000002391 heterocyclic compounds Chemical class 0.000 description 1
• ALBYIUDWACNRRB-UHFFFAOYSA-N hexanamide Chemical compound CCCCCC(N)=O ALBYIUDWACNRRB-UHFFFAOYSA-N 0.000 description 1
• 238000004896 high resolution mass spectrometry Methods 0.000 description 1
• HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
• 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 1
• XGIHQYAWBCFNPY-AZOCGYLKSA-N hydrabamine Chemical compound C([C@@H]12)CC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC[C@@]1(C)CNCCNC[C@@]1(C)[C@@H]2CCC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC1 XGIHQYAWBCFNPY-AZOCGYLKSA-N 0.000 description 1
• 150000004677 hydrates Chemical class 0.000 description 1
• 229930195733 hydrocarbon Natural products 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
• 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
• 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
• 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
• 239000003326 hypnotic agent Substances 0.000 description 1
• 230000000147 hypnotic effect Effects 0.000 description 1
• 239000005457 ice water Substances 0.000 description 1
• 239000002117 illicit drug Substances 0.000 description 1
• 125000002883 imidazolyl group Chemical group 0.000 description 1
• 125000004857 imidazopyridinyl group Chemical class N1C(=NC2=C1C=CC=N2)* 0.000 description 1
• BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 1
• 229960004801 imipramine Drugs 0.000 description 1
• 210000000987 immune system Anatomy 0.000 description 1
• 230000001771 impaired effect Effects 0.000 description 1
• 230000002779 inactivation Effects 0.000 description 1
• 125000003453 indazolyl group Chemical class N1N=C(C2=C1C=CC=C2)* 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
• LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical compound C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 description 1
• 208000015181 infectious disease Diseases 0.000 description 1
• 230000010365 information processing Effects 0.000 description 1
• 230000002401 inhibitory effect Effects 0.000 description 1
• 229940102223 injectable solution Drugs 0.000 description 1
• 229940102213 injectable suspension Drugs 0.000 description 1
• 238000002347 injection Methods 0.000 description 1
• 239000007924 injection Substances 0.000 description 1
• 239000002198 insoluble material Substances 0.000 description 1
• 206010022437 insomnia Diseases 0.000 description 1
• 230000002452 interceptive effect Effects 0.000 description 1
• SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
• 239000003456 ion exchange resin Substances 0.000 description 1
• 229920003303 ion-exchange polymer Polymers 0.000 description 1
• 230000000302 ischemic effect Effects 0.000 description 1
• AWJUIBRHMBBTKR-UHFFFAOYSA-N iso-quinoline Natural products C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 1
• JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
• 125000005956 isoquinolyl group Chemical group 0.000 description 1
• 125000003971 isoxazolinyl group Chemical group 0.000 description 1
• 150000002576 ketones Chemical class 0.000 description 1
• 239000008101 lactose Substances 0.000 description 1
• 238000002430 laser surgery Methods 0.000 description 1
• 230000002045 lasting effect Effects 0.000 description 1
• CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 1
• 239000003446 ligand Substances 0.000 description 1
• 108020001756 ligand binding domains Proteins 0.000 description 1
• 238000000622 liquid--liquid extraction Methods 0.000 description 1
• 239000012280 lithium aluminium hydride Substances 0.000 description 1
• 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 1
• GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 1
• UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
• 230000003137 locomotive effect Effects 0.000 description 1
• 229960004391 lorazepam Drugs 0.000 description 1
• 210000003141 lower extremity Anatomy 0.000 description 1
• 229960000423 loxapine Drugs 0.000 description 1
• YQZBAXDVDZTKEQ-UHFFFAOYSA-N loxapine succinate Chemical compound [H+].[H+].[O-]C(=O)CCC([O-])=O.C1CN(C)CCN1C1=NC2=CC=CC=C2OC2=CC=C(Cl)C=C12 YQZBAXDVDZTKEQ-UHFFFAOYSA-N 0.000 description 1
• 239000007937 lozenge Substances 0.000 description 1
• 239000000314 lubricant Substances 0.000 description 1
• 239000011777 magnesium Substances 0.000 description 1
• 229910052749 magnesium Inorganic materials 0.000 description 1
• 239000000395 magnesium oxide Substances 0.000 description 1
• CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
• 235000019359 magnesium stearate Nutrition 0.000 description 1
• AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 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
• 229940118019 malondialdehyde Drugs 0.000 description 1
• 210000004962 mammalian cell Anatomy 0.000 description 1
• 238000004949 mass spectrometry Methods 0.000 description 1
• 238000005259 measurement Methods 0.000 description 1
• 238000002483 medication Methods 0.000 description 1
• 230000004630 mental health Effects 0.000 description 1
• SLVMESMUVMCQIY-UHFFFAOYSA-N mesoridazine Chemical compound CN1CCCCC1CCN1C2=CC(S(C)=O)=CC=C2SC2=CC=CC=C21 SLVMESMUVMCQIY-UHFFFAOYSA-N 0.000 description 1
• 229960000300 mesoridazine Drugs 0.000 description 1
• 102000006239 metabotropic receptors Human genes 0.000 description 1
• 108020004083 metabotropic receptors Proteins 0.000 description 1
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
• MXNIODZSMNMILW-UHFFFAOYSA-N methyl 2-acetamido-2-dimethoxyphosphorylacetate Chemical compound COC(=O)C(NC(C)=O)P(=O)(OC)OC MXNIODZSMNMILW-UHFFFAOYSA-N 0.000 description 1
• MKIJJIMOAABWGF-UHFFFAOYSA-N methyl 2-sulfanylacetate Chemical compound COC(=O)CS MKIJJIMOAABWGF-UHFFFAOYSA-N 0.000 description 1
• SUHXBEISAFXKIN-UHFFFAOYSA-N methyl thieno[2,3-b]pyridine-2-carboxylate Chemical compound C1=CN=C2SC(C(=O)OC)=CC2=C1 SUHXBEISAFXKIN-UHFFFAOYSA-N 0.000 description 1
• LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
• XLTANAWLDBYGFU-VTLKBQQISA-N methyllycaconitine Chemical compound C([C@]12CN([C@@H]3[C@@]4(O)[C@]5(O)[C@H]6[C@@H](OC)[C@@H]([C@H](C5)OC)C[C@H]6[C@@]3([C@@H]1[C@@H]4OC)[C@@H](OC)CC2)CC)OC(=O)C1=CC=CC=C1N1C(=O)C[C@H](C)C1=O XLTANAWLDBYGFU-VTLKBQQISA-N 0.000 description 1
• FRZAEBZEHFXWKR-UHFFFAOYSA-N methyllycaconitine Natural products CCN1CC2(COC(=O)c3ccccc3N4C(=O)CC(C)C4=O)CCC(O)C56C7CC8C(O)C7C(O)(CC8OC)C(O)(C(OC)C25)C16 FRZAEBZEHFXWKR-UHFFFAOYSA-N 0.000 description 1
• 125000002950 monocyclic group Chemical group 0.000 description 1
• 239000012452 mother liquor Substances 0.000 description 1
• 230000037023 motor activity Effects 0.000 description 1
• 208000005264 motor neuron disease Diseases 0.000 description 1
• 239000000472 muscarinic agonist Substances 0.000 description 1
• 230000035772 mutation Effects 0.000 description 1
• 230000002107 myocardial effect Effects 0.000 description 1
• ACTNHJDHMQSOGL-UHFFFAOYSA-N n',n'-dibenzylethane-1,2-diamine Chemical compound C=1C=CC=CC=1CN(CCN)CC1=CC=CC=C1 ACTNHJDHMQSOGL-UHFFFAOYSA-N 0.000 description 1
• QNRQFXFYSOYZRI-UHFFFAOYSA-N n-(1-azabicyclo[2.2.1]heptan-3-yl)-1-methylpyrrolo[2,3-c]pyridine-5-carboxamide Chemical compound C1=C2N(C)C=CC2=CC(C(=O)NC2C3CCN(C3)C2)=N1 QNRQFXFYSOYZRI-UHFFFAOYSA-N 0.000 description 1
• LHQWXJTWVJYOAE-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-2-yl)-1h-indole-2-carboxamide Chemical class C1=CC=C2NC(C(NC3N4CCC(CC4)C3)=O)=CC2=C1 LHQWXJTWVJYOAE-UHFFFAOYSA-N 0.000 description 1
• NRIBIZDDLCKYAI-UHFFFAOYSA-N n-(1-azabicyclo[3.2.2]nonan-3-yl)furo[2,3-b]pyridine-2-carboxamide Chemical compound C1CN(C2)CCC1CC2NC(=O)C1=CC2=CC=CN=C2O1 NRIBIZDDLCKYAI-UHFFFAOYSA-N 0.000 description 1
• ZXRIIBXZJMEXEL-WLHGVMLRSA-N n-(1-azabicyclo[3.2.2]nonan-3-yl)furo[2,3-c]pyridine-5-carboxamide;(e)-but-2-enedioic acid Chemical compound OC(=O)\C=C\C(O)=O.C1CN(C2)CCC1CC2NC(=O)C(N=C1)=CC2=C1OC=C2 ZXRIIBXZJMEXEL-WLHGVMLRSA-N 0.000 description 1
• PTWBCENGUOUJTM-UHFFFAOYSA-N n-(1-azabicyclo[3.2.2]nonan-3-yl)thieno[2,3-c]pyridine-2-carboxamide Chemical compound C1CN(C2)CCC1CC2NC(=O)C1=CC2=CC=NC=C2S1 PTWBCENGUOUJTM-UHFFFAOYSA-N 0.000 description 1
• OWVSGLPSSZYJEP-UHFFFAOYSA-N n-(2-azabicyclo[2.2.1]heptan-5-yl)-1-methylpyrrolo[2,3-c]pyridine-5-carboxamide Chemical compound C1=C2N(C)C=CC2=CC(C(=O)NC2C3CC(NC3)C2)=N1 OWVSGLPSSZYJEP-UHFFFAOYSA-N 0.000 description 1
• ODQKKSFEJMAOHM-UHFFFAOYSA-N n-(2-azabicyclo[2.2.1]heptan-5-yl)-2-chlorofuro[3,2-c]pyridine-6-carboxamide Chemical compound C1=C2OC(Cl)=CC2=CN=C1C(=O)NC1C(CN2)CC2C1 ODQKKSFEJMAOHM-UHFFFAOYSA-N 0.000 description 1
• NCYGPPFYAODECX-UHFFFAOYSA-N n-(2-azabicyclo[2.2.1]heptan-5-yl)-2-ethynylfuro[3,2-c]pyridine-6-carboxamide Chemical compound C1C(NC2)CC2C1NC(=O)C(N=C1)=CC2=C1C=C(C#C)O2 NCYGPPFYAODECX-UHFFFAOYSA-N 0.000 description 1
• ODHHWESCMDQDRQ-UHFFFAOYSA-N n-(2-azabicyclo[2.2.1]heptan-5-yl)-2-fluorofuro[3,2-c]pyridine-6-carboxamide Chemical compound C1=C2OC(F)=CC2=CN=C1C(=O)NC1C(CN2)CC2C1 ODHHWESCMDQDRQ-UHFFFAOYSA-N 0.000 description 1
• CYZOAVRFJVDBKN-UHFFFAOYSA-N n-(2-azabicyclo[2.2.1]heptan-5-yl)-3-ethynylfuro[2,3-c]pyridine-5-carboxamide Chemical compound C1C(NC2)CC2C1NC(=O)C(N=C1)=CC2=C1OC=C2C#C CYZOAVRFJVDBKN-UHFFFAOYSA-N 0.000 description 1
• FNICXWBUDFSTRG-UHFFFAOYSA-N n-(2-azabicyclo[2.2.1]heptan-5-yl)-3-formylfuro[2,3-c]pyridine-5-carboxamide Chemical compound C1=C2C(C=O)=COC2=CN=C1C(=O)NC1C(CN2)CC2C1 FNICXWBUDFSTRG-UHFFFAOYSA-N 0.000 description 1
• HDECJGZLRBSYLQ-UHFFFAOYSA-N n-(2-azabicyclo[2.2.1]heptan-5-yl)thieno[3,2-b]pyridine-2-carboxamide Chemical compound C1=CC=C2SC(C(NC3C4CC(NC4)C3)=O)=CC2=N1 HDECJGZLRBSYLQ-UHFFFAOYSA-N 0.000 description 1
• INJNJEDOJPDPND-UHFFFAOYSA-N n-(3-azabicyclo[2.2.1]heptan-5-yl)thieno[3,2-b]pyridine-2-carboxamide Chemical compound C1=CC=C2SC(C(NC3C4NCC(C4)C3)=O)=CC2=N1 INJNJEDOJPDPND-UHFFFAOYSA-N 0.000 description 1
• JJXXPSSVMROTBY-MWLCHTKSSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-2-(trifluoromethyl)furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC(C(F)(F)F)=C2 JJXXPSSVMROTBY-MWLCHTKSSA-N 0.000 description 1
• HDUCRXAGWRGVPD-MWLCHTKSSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-2-bromofuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC(Br)=C2 HDUCRXAGWRGVPD-MWLCHTKSSA-N 0.000 description 1
• NZWYCFPHNHLLLR-MWLCHTKSSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-2-bromothieno[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(Br)S2 NZWYCFPHNHLLLR-MWLCHTKSSA-N 0.000 description 1
• QONBWAJUVOCXLO-MWLCHTKSSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-2-chlorofuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC(Cl)=C2 QONBWAJUVOCXLO-MWLCHTKSSA-N 0.000 description 1
• ZOXDTYARCQQQEM-ZYHUDNBSSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-2-cyanofuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC(C#N)=C2 ZOXDTYARCQQQEM-ZYHUDNBSSA-N 0.000 description 1
• RLCMRQNMJSIQJW-DGCLKSJQSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-2-ethenylthieno[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(C=C)S2 RLCMRQNMJSIQJW-DGCLKSJQSA-N 0.000 description 1
• ZVUZEUMRIRBLTE-MWLCHTKSSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-2-fluorofuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC(F)=C2 ZVUZEUMRIRBLTE-MWLCHTKSSA-N 0.000 description 1
• QGCATBMMZTVKKL-MWLCHTKSSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-2-iodofuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC(I)=C2 QGCATBMMZTVKKL-MWLCHTKSSA-N 0.000 description 1
• CRBKTJVPVPRNFV-MWLCHTKSSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-2-iodofuro[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(I)O2 CRBKTJVPVPRNFV-MWLCHTKSSA-N 0.000 description 1
• GRVJQUTVWPFUAP-ZYHUDNBSSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-3-cyanothieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1SC=C2C#N GRVJQUTVWPFUAP-ZYHUDNBSSA-N 0.000 description 1
• AURVACGZWSGPCY-NXEZZACHSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-3-sulfanylfuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC=C2S AURVACGZWSGPCY-NXEZZACHSA-N 0.000 description 1
• MYMRUXISGMLQAH-GHMZBOCLSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-4-methoxythieno[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1OC)=CC2=C1C=CS2 MYMRUXISGMLQAH-GHMZBOCLSA-N 0.000 description 1
• VJQBBQSYMZFMJY-VXGBXAGGSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-4-methylthieno[3,2-c]pyridine-6-carbothioamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=S)C(N=C1C)=CC2=C1C=CS2 VJQBBQSYMZFMJY-VXGBXAGGSA-N 0.000 description 1
• SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
• 239000004081 narcotic agent Substances 0.000 description 1
• 230000010004 neural pathway Effects 0.000 description 1
• 208000004296 neuralgia Diseases 0.000 description 1
• 230000007107 neurocognitive deficit Effects 0.000 description 1
• 208000015122 neurodegenerative disease Diseases 0.000 description 1
• 230000004112 neuroprotection Effects 0.000 description 1
• 239000004090 neuroprotective agent Substances 0.000 description 1
• 230000000324 neuroprotective effect Effects 0.000 description 1
• 208000015238 neurotic disease Diseases 0.000 description 1
• 230000003957 neurotransmitter release Effects 0.000 description 1
• LHLRIVKZRMTHAH-UHFFFAOYSA-N nitroso 2-methylpropanoate Chemical compound CC(C)C(=O)ON=O LHLRIVKZRMTHAH-UHFFFAOYSA-N 0.000 description 1
• QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
• OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
• JASMWYNKLTULAN-UHFFFAOYSA-N octan-3-amine Chemical class CCCCCC(N)CC JASMWYNKLTULAN-UHFFFAOYSA-N 0.000 description 1
• JSEKKSKUONNSQM-UHFFFAOYSA-N octan-3-amine;hydrochloride Chemical compound [Cl-].CCCCCC([NH3+])CC JSEKKSKUONNSQM-UHFFFAOYSA-N 0.000 description 1
• 229960005017 olanzapine Drugs 0.000 description 1
• 210000000287 oocyte Anatomy 0.000 description 1
• 229940005483 opioid analgesics Drugs 0.000 description 1
• 210000001328 optic nerve Anatomy 0.000 description 1
• GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 1
• YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
• 229920002866 paraformaldehyde Polymers 0.000 description 1
• 201000007620 paralytic ileus Diseases 0.000 description 1
• 238000007911 parenteral administration Methods 0.000 description 1
• 229960002296 paroxetine Drugs 0.000 description 1
• 239000004031 partial agonist Substances 0.000 description 1
• 230000036961 partial effect Effects 0.000 description 1
• 235000011837 pasties Nutrition 0.000 description 1
• 230000001717 pathogenic effect Effects 0.000 description 1
• 231100000915 pathological change Toxicity 0.000 description 1
• 230000036285 pathological change Effects 0.000 description 1
• 230000007170 pathology Effects 0.000 description 1
• 239000000312 peanut oil Substances 0.000 description 1
• NRNCYVBFPDDJNE-UHFFFAOYSA-N pemoline Chemical compound O1C(N)=NC(=O)C1C1=CC=CC=C1 NRNCYVBFPDDJNE-UHFFFAOYSA-N 0.000 description 1
• 229960000761 pemoline Drugs 0.000 description 1
• 230000000149 penetrating effect Effects 0.000 description 1
• 230000008447 perception Effects 0.000 description 1
• 229960000762 perphenazine Drugs 0.000 description 1
• 230000002688 persistence Effects 0.000 description 1
• DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
• 229960002695 phenobarbital Drugs 0.000 description 1
• WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
• 208000019899 phobic disease Diseases 0.000 description 1
• RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
• 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 description 1
• XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
• 230000010254 physiological adaptation Effects 0.000 description 1
• 230000004962 physiological condition Effects 0.000 description 1
• 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
• 229920000768 polyamine Polymers 0.000 description 1
• 206010036067 polydipsia Diseases 0.000 description 1
• 229920001223 polyethylene glycol Polymers 0.000 description 1
• 229920000642 polymer Polymers 0.000 description 1
• 229920002451 polyvinyl alcohol Polymers 0.000 description 1
• 239000011148 porous material Substances 0.000 description 1
• 229910052700 potassium Inorganic materials 0.000 description 1
• 239000011591 potassium Substances 0.000 description 1
• 108020001213 potassium channel Chemical group 0.000 description 1
• 238000001556 precipitation Methods 0.000 description 1
• 230000002265 prevention Effects 0.000 description 1
• MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
• 229960004919 procaine Drugs 0.000 description 1
• 102000004196 processed proteins & peptides Human genes 0.000 description 1
• 108090000765 processed proteins & peptides Proteins 0.000 description 1
• WIKYUJGCLQQFNW-UHFFFAOYSA-N prochlorperazine Chemical compound C1CN(C)CCN1CCCN1C2=CC(Cl)=CC=C2SC2=CC=CC=C21 WIKYUJGCLQQFNW-UHFFFAOYSA-N 0.000 description 1
• 229960003111 prochlorperazine Drugs 0.000 description 1
• 230000007425 progressive decline Effects 0.000 description 1
• 230000000750 progressive effect Effects 0.000 description 1
• 230000002035 prolonged effect Effects 0.000 description 1
• 229960003598 promazine Drugs 0.000 description 1
• 235000013772 propylene glycol Nutrition 0.000 description 1
• 102000004169 proteins and genes Human genes 0.000 description 1
• 239000003196 psychodysleptic agent Substances 0.000 description 1
• 150000003212 purines Chemical class 0.000 description 1
• 125000003373 pyrazinyl group Chemical group 0.000 description 1
• DVUBDHRTVYLIPA-UHFFFAOYSA-N pyrazolo[1,5-a]pyridine Chemical class C1=CC=CN2N=CC=C21 DVUBDHRTVYLIPA-UHFFFAOYSA-N 0.000 description 1
• HRSDPDBQVZHCRC-UHFFFAOYSA-N pyrazolo[1,5-a]pyridine-3-carboxylic acid Chemical class C1=CC=CC2=C(C(=O)O)C=NN21 HRSDPDBQVZHCRC-UHFFFAOYSA-N 0.000 description 1
• 150000004892 pyridazines Chemical class 0.000 description 1
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
• 125000000714 pyrimidinyl group Chemical group 0.000 description 1
• URKOMYMAXPYINW-UHFFFAOYSA-N quetiapine Chemical compound C1CN(CCOCCO)CCN1C1=NC2=CC=CC=C2SC2=CC=CC=C12 URKOMYMAXPYINW-UHFFFAOYSA-N 0.000 description 1
• 229960004431 quetiapine Drugs 0.000 description 1
• ZTHJULTYCAQOIJ-WXXKFALUSA-N quetiapine fumarate Chemical compound [H+].[H+].[O-]C(=O)\C=C\C([O-])=O.C1CN(CCOCCO)CCN1C1=NC2=CC=CC=C2SC2=CC=CC=C12.C1CN(CCOCCO)CCN1C1=NC2=CC=CC=C2SC2=CC=CC=C12 ZTHJULTYCAQOIJ-WXXKFALUSA-N 0.000 description 1
• SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical group C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
• 238000001959 radiotherapy Methods 0.000 description 1
• 230000008707 rearrangement Effects 0.000 description 1
• 238000001953 recrystallisation Methods 0.000 description 1
• 230000001105 regulatory effect Effects 0.000 description 1
• 230000000241 respiratory effect Effects 0.000 description 1
• 230000004044 response Effects 0.000 description 1
• 210000001525 retina Anatomy 0.000 description 1
• 230000002441 reversible effect Effects 0.000 description 1
• 206010039083 rhinitis Diseases 0.000 description 1
• 230000001020 rhythmical effect Effects 0.000 description 1
• 229960004181 riluzole Drugs 0.000 description 1
• 125000006413 ring segment Chemical group 0.000 description 1
• 229940106887 risperdal Drugs 0.000 description 1
• 229960001534 risperidone Drugs 0.000 description 1
• 239000012047 saturated solution Substances 0.000 description 1
• 238000012216 screening Methods 0.000 description 1
• 150000003335 secondary amines Chemical class 0.000 description 1
• 229940125723 sedative agent Drugs 0.000 description 1
• 239000000932 sedative agent Substances 0.000 description 1
• 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 description 1
• 239000012896 selective serotonin reuptake inhibitor Substances 0.000 description 1
• 230000035945 sensitivity Effects 0.000 description 1
• 230000021317 sensory perception Effects 0.000 description 1
• 229940035004 seroquel Drugs 0.000 description 1
• 230000000862 serotonergic effect Effects 0.000 description 1
• 239000003523 serotonin 4 antagonist Substances 0.000 description 1
• 239000000198 serotonin 5-HT3 receptor agonist Substances 0.000 description 1
• 239000000387 serotonin 5-HT4 receptor agonist Substances 0.000 description 1
• 229940121356 serotonin receptor antagonist Drugs 0.000 description 1
• 230000002295 serotoninergic effect Effects 0.000 description 1
• 229960002073 sertraline Drugs 0.000 description 1
• VGKDLMBJGBXTGI-SJCJKPOMSA-N sertraline Chemical compound C1([C@@H]2CC[C@@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 VGKDLMBJGBXTGI-SJCJKPOMSA-N 0.000 description 1
• 239000008159 sesame oil Substances 0.000 description 1
• 235000011803 sesame oil Nutrition 0.000 description 1
• 230000001568 sexual effect Effects 0.000 description 1
• 210000003625 skull Anatomy 0.000 description 1
• 239000000779 smoke Substances 0.000 description 1
• 239000000661 sodium alginate Substances 0.000 description 1
• 235000010413 sodium alginate Nutrition 0.000 description 1
• 229940005550 sodium alginate Drugs 0.000 description 1
• 125000004436 sodium atom Chemical group 0.000 description 1
• HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
• 235000019254 sodium formate Nutrition 0.000 description 1
• RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
• 238000000638 solvent extraction Methods 0.000 description 1
• 241000894007 species Species 0.000 description 1
• 210000000278 spinal cord Anatomy 0.000 description 1
• 239000001119 stannous chloride Substances 0.000 description 1
• 235000011150 stannous chloride Nutrition 0.000 description 1
• 239000007858 starting material Substances 0.000 description 1
• 239000008117 stearic acid Substances 0.000 description 1
• 230000000638 stimulation Effects 0.000 description 1
• 239000012258 stirred mixture Substances 0.000 description 1
• 210000002784 stomach Anatomy 0.000 description 1
• 238000003860 storage Methods 0.000 description 1
• 238000010254 subcutaneous injection Methods 0.000 description 1
• 239000007929 subcutaneous injection Substances 0.000 description 1
• 239000005720 sucrose Substances 0.000 description 1
• 239000006228 supernatant Substances 0.000 description 1
• 230000004083 survival effect Effects 0.000 description 1
• 238000013268 sustained release Methods 0.000 description 1
• 230000009897 systematic effect Effects 0.000 description 1
• 230000006794 tachycardia Effects 0.000 description 1
• 239000000454 talc Substances 0.000 description 1
• 229910052623 talc Inorganic materials 0.000 description 1
• 239000011975 tartaric acid Substances 0.000 description 1
• 235000002906 tartaric acid Nutrition 0.000 description 1
• ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
• UNUNCPXYUNVRRF-UHFFFAOYSA-N tert-butyl 4-(2-oxopropyl)piperidine-1-carboxylate Chemical compound CC(=O)CC1CCN(C(=O)OC(C)(C)C)CC1 UNUNCPXYUNVRRF-UHFFFAOYSA-N 0.000 description 1
• DVXZTYVDRMTHSV-UHFFFAOYSA-N tert-butyl 4-(2-oxopropylidene)piperidine-1-carboxylate Chemical compound CC(=O)C=C1CCN(C(=O)OC(C)(C)C)CC1 DVXZTYVDRMTHSV-UHFFFAOYSA-N 0.000 description 1
• XYDJXFFRMCPJRH-UHFFFAOYSA-N tert-butyl 4-(3-bromo-2-oxopropyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(CC(=O)CBr)CC1 XYDJXFFRMCPJRH-UHFFFAOYSA-N 0.000 description 1
• ROUYFJUVMYHXFJ-UHFFFAOYSA-N tert-butyl 4-oxopiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(=O)CC1 ROUYFJUVMYHXFJ-UHFFFAOYSA-N 0.000 description 1
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
• NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 1
• 125000003831 tetrazolyl group Chemical group 0.000 description 1
• 230000003461 thalamocortical effect Effects 0.000 description 1
• 229960004559 theobromine Drugs 0.000 description 1
• 229940124597 therapeutic agent Drugs 0.000 description 1
• 125000000335 thiazolyl group Chemical group 0.000 description 1
• SMZMHUCIDGHERP-UHFFFAOYSA-N thieno[2,3-b]pyridine Chemical compound C1=CN=C2SC=CC2=C1 SMZMHUCIDGHERP-UHFFFAOYSA-N 0.000 description 1
• XGCSHAYMNOFFNA-UHFFFAOYSA-N thieno[2,3-b]pyridine-2-carboxylic acid Chemical compound C1=CN=C2SC(C(=O)O)=CC2=C1 XGCSHAYMNOFFNA-UHFFFAOYSA-N 0.000 description 1
• IOVJNINZHOJSDD-UHFFFAOYSA-N thieno[2,3-b]pyridine-5-carbonitrile Chemical compound N#CC1=CN=C2SC=CC2=C1 IOVJNINZHOJSDD-UHFFFAOYSA-N 0.000 description 1
• JDWFURAFRCAVOH-UHFFFAOYSA-N thieno[2,3-b]pyridine-5-carboxylic acid Chemical compound OC(=O)C1=CN=C2SC=CC2=C1 JDWFURAFRCAVOH-UHFFFAOYSA-N 0.000 description 1
• KTSOZLHVFLYDNN-UHFFFAOYSA-N thieno[2,3-b]pyridine-6-carbonitrile Chemical compound N#CC1=CC=C2C=CSC2=N1 KTSOZLHVFLYDNN-UHFFFAOYSA-N 0.000 description 1
• MJUWERVDNLIFQL-UHFFFAOYSA-N thieno[2,3-b]pyridine-6-carboxylic acid Chemical compound OC(=O)C1=CC=C2C=CSC2=N1 MJUWERVDNLIFQL-UHFFFAOYSA-N 0.000 description 1
• GDQBPBMIAFIRIU-UHFFFAOYSA-N thieno[2,3-c]pyridine Chemical compound C1=NC=C2SC=CC2=C1 GDQBPBMIAFIRIU-UHFFFAOYSA-N 0.000 description 1
• MVAMOERRWMZNPJ-UHFFFAOYSA-N thieno[2,3-c]pyridine-2-carboxamide Chemical compound C1=NC=C2SC(C(=O)N)=CC2=C1 MVAMOERRWMZNPJ-UHFFFAOYSA-N 0.000 description 1
• DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical class C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 description 1
• 125000001544 thienyl group Chemical group 0.000 description 1
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 1
• GLQWRXYOTXRDNH-UHFFFAOYSA-N thiophen-2-amine Chemical compound NC1=CC=CS1 GLQWRXYOTXRDNH-UHFFFAOYSA-N 0.000 description 1
• 229960002784 thioridazine Drugs 0.000 description 1
• 229960005013 tiotixene Drugs 0.000 description 1
• 230000008467 tissue growth Effects 0.000 description 1
• 231100000331 toxic Toxicity 0.000 description 1
• 230000002588 toxic effect Effects 0.000 description 1
• 230000008733 trauma Effects 0.000 description 1
• 125000004306 triazinyl group Chemical group 0.000 description 1
• 125000001425 triazolyl group Chemical group 0.000 description 1
• DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
• 239000003029 tricyclic antidepressant agent Substances 0.000 description 1
• 229960002324 trifluoperazine Drugs 0.000 description 1
• 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
• 230000001960 triggered effect Effects 0.000 description 1
• ULYLMHUHFUQKOE-UHFFFAOYSA-N trimethyl(prop-2-ynyl)silane Chemical compound C[Si](C)(C)CC#C ULYLMHUHFUQKOE-UHFFFAOYSA-N 0.000 description 1
• PRXNKYBFWAWBNZ-UHFFFAOYSA-N trimethylphenylammonium tribromide Chemical compound Br[Br-]Br.C[N+](C)(C)C1=CC=CC=C1 PRXNKYBFWAWBNZ-UHFFFAOYSA-N 0.000 description 1
• LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
• CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
• YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
• ZNRGQMMCGHDTEI-ITGUQSILSA-N tropisetron Chemical compound C1=CC=C2C(C(=O)O[C@H]3C[C@H]4CC[C@@H](C3)N4C)=CNC2=C1 ZNRGQMMCGHDTEI-ITGUQSILSA-N 0.000 description 1
• 229960003688 tropisetron Drugs 0.000 description 1
• 210000001364 upper extremity Anatomy 0.000 description 1
• JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
• 125000005500 uronium group Chemical group 0.000 description 1
• 238000003828 vacuum filtration Methods 0.000 description 1
• 239000003981 vehicle Substances 0.000 description 1
• 208000009935 visceral pain Diseases 0.000 description 1
• 230000001755 vocal effect Effects 0.000 description 1
• 239000003039 volatile agent Substances 0.000 description 1
• 238000010792 warming Methods 0.000 description 1
• 239000000080 wetting agent Substances 0.000 description 1
• 150000003751 zinc Chemical class 0.000 description 1
• 239000011592 zinc chloride Substances 0.000 description 1
• 235000005074 zinc chloride Nutrition 0.000 description 1
• 229960000607 ziprasidone Drugs 0.000 description 1
• 229940039925 zyprexa Drugs 0.000 description 1