ES2529119T3 - Compuestos heterocíclicos condensados como moduladores de canales iónicos - Google Patents

Info

Publication number

ES2529119T3

ES2529119T3 ES11732540.7T ES11732540T ES2529119T3 ES 2529119 T3 ES2529119 T3 ES 2529119T3 ES 11732540 T ES11732540 T ES 11732540T ES 2529119 T3 ES2529119 T3 ES 2529119T3

Authority

ES

Spain

Prior art keywords

pyridin

phenyl

triazolo

trifluoromethoxy

methyl

Prior art date

2010-07-02

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Active

Links

• Espacenet
• Global Dossier
• Discuss

• 102000004310 Ion Channels Human genes 0.000 title description 6
• 150000002391 heterocyclic compounds Chemical class 0.000 title description 2
• -1 -O-CHF2 Chemical group 0.000 claims abstract description 520
• 125000003118 aryl group Chemical group 0.000 claims abstract description 171
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 147
• 125000001424 substituent group Chemical group 0.000 claims abstract description 143
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 131
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 113
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 109
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 106
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 98
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 67
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 57
• 239000001257 hydrogen Substances 0.000 claims abstract description 57
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 56
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 52
• 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 49
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 47
• 150000002431 hydrogen Chemical group 0.000 claims abstract description 44
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 35
• 125000001475 halogen functional group Chemical group 0.000 claims abstract description 32
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 31
• 125000000304 alkynyl group Chemical group 0.000 claims abstract description 29
• 150000003839 salts Chemical class 0.000 claims abstract description 29
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims abstract description 27
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims abstract description 27
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 22
• 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 22
• 150000002148 esters Chemical class 0.000 claims abstract description 20
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 19
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 18
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims abstract description 16
• 125000002252 acyl group Chemical group 0.000 claims abstract description 16
• 229910052805 deuterium Inorganic materials 0.000 claims abstract description 16
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 15
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims abstract description 13
• 239000012453 solvate Substances 0.000 claims abstract description 12
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 11
• 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 10
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims abstract description 9
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
• 125000002102 aryl alkyloxo group Chemical group 0.000 claims abstract description 7
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims abstract description 6
• 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 5
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 5
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract description 3
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 3
• 125000005415 substituted alkoxy group Chemical group 0.000 claims abstract 2
• 150000001875 compounds Chemical class 0.000 claims description 367
• 239000011734 sodium Substances 0.000 claims description 153
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 50
• 238000000034 method Methods 0.000 claims description 49
• 229910052708 sodium Inorganic materials 0.000 claims description 35
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 33
• 239000003795 chemical substances by application Substances 0.000 claims description 19
• GKECDORWWXXNRY-UHFFFAOYSA-N 2h-pyridin-3-one Chemical compound O=C1CN=CC=C1 GKECDORWWXXNRY-UHFFFAOYSA-N 0.000 claims description 18
• 230000007170 pathology Effects 0.000 claims description 16
• 206010019280 Heart failures Diseases 0.000 claims description 15
• 125000004104 aryloxy group Chemical group 0.000 claims description 12
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 12
• 229940002612 prodrug Drugs 0.000 claims description 11
• 239000000651 prodrug Substances 0.000 claims description 11
• 206010007559 Cardiac failure congestive Diseases 0.000 claims description 10
• 241000124008 Mammalia Species 0.000 claims description 10
• 208000028867 ischemia Diseases 0.000 claims description 10
• 239000008194 pharmaceutical composition Substances 0.000 claims description 10
• 208000005764 Peripheral Arterial Disease Diseases 0.000 claims description 9
• 208000030831 Peripheral arterial occlusive disease Diseases 0.000 claims description 9
• 206010012601 diabetes mellitus Diseases 0.000 claims description 9
• UCOVZXULYPKXSE-UHFFFAOYSA-N 2-[[3-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound O1C(C)=NC(C=2C=C(CN3C(N4C=C(C=CC4=N3)C=3C=CC(OC(F)(F)F)=CC=3)=O)C=CC=2)=N1 UCOVZXULYPKXSE-UHFFFAOYSA-N 0.000 claims description 8
• IBWDGDOOVUPPRH-UHFFFAOYSA-N 2-methyl-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C=1N2C(=O)N(C)N=C2C=CC=1C1=CC=C(OC(F)(F)F)C=C1 IBWDGDOOVUPPRH-UHFFFAOYSA-N 0.000 claims description 8
• 206010002383 Angina Pectoris Diseases 0.000 claims description 8
• 206010002388 Angina unstable Diseases 0.000 claims description 8
• 206010022562 Intermittent claudication Diseases 0.000 claims description 8
• 208000007814 Unstable Angina Diseases 0.000 claims description 8
• 201000004332 intermediate coronary syndrome Diseases 0.000 claims description 8
• QFDHIAJTTBECEF-UHFFFAOYSA-N 2-(2-imidazo[1,2-a]pyrazin-8-yloxyethyl)-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCOC=3C4=NC=CN4C=CN=3)N=C2C=C1 QFDHIAJTTBECEF-UHFFFAOYSA-N 0.000 claims description 7
• BULIWKSBFXZAGF-UHFFFAOYSA-N 2-(2-pyridin-2-ylpropyl)-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C=1C=CC=NC=1C(C)CN(C(N1C=2)=O)N=C1C=CC=2C1=CC=C(OC(F)(F)F)C=C1 BULIWKSBFXZAGF-UHFFFAOYSA-N 0.000 claims description 7
• QSGFIGSRPYAVMI-UHFFFAOYSA-N 2-(3-pyrazin-2-yloxypropyl)-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCCOC=3N=CC=NC=3)N=C2C=C1 QSGFIGSRPYAVMI-UHFFFAOYSA-N 0.000 claims description 7
• ULQSVPQTXFDRBR-UHFFFAOYSA-N 2-(4-pyrimidin-2-yloxyoxolan-3-yl)-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(C3C(COC3)OC=3N=CC=CN=3)N=C2C=C1 ULQSVPQTXFDRBR-UHFFFAOYSA-N 0.000 claims description 7
• OUOIJRKIRMVJNR-UHFFFAOYSA-N 2-(quinolin-2-ylmethyl)-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CC=3N=C4C=CC=CC4=CC=3)N=C2C=C1 OUOIJRKIRMVJNR-UHFFFAOYSA-N 0.000 claims description 7
• CSOAIKTXKJYPAL-UHFFFAOYSA-N 2-[1-(3-methyl-1,2,4-oxadiazol-5-yl)ethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound N1=C2C=CC(C=3C=CC(OC(F)(F)F)=CC=3)=CN2C(=O)N1C(C)C1=NC(C)=NO1 CSOAIKTXKJYPAL-UHFFFAOYSA-N 0.000 claims description 7
• UUEZDKYARYKPTK-UHFFFAOYSA-N 2-[2-(4-cyclopropylpyrimidin-2-yl)oxyethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCOC=3N=C(C=CN=3)C3CC3)N=C2C=C1 UUEZDKYARYKPTK-UHFFFAOYSA-N 0.000 claims description 7
• HGTRMKUOOYDDBC-JOCHJYFZSA-N 2-[2-[(3r)-3-(4-fluorophenoxy)pyrrolidin-1-yl]ethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(F)=CC=C1O[C@H]1CN(CCN2C(N3C=C(C=CC3=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)CC1 HGTRMKUOOYDDBC-JOCHJYFZSA-N 0.000 claims description 7
• YQPKTLJATZYGSK-UHFFFAOYSA-N 2-[2-hydroxy-3-(2-phenylphenoxy)propyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound N1=C2C=CC(C=3C=CC(OC(F)(F)F)=CC=3)=CN2C(=O)N1CC(O)COC1=CC=CC=C1C1=CC=CC=C1 YQPKTLJATZYGSK-UHFFFAOYSA-N 0.000 claims description 7
• YWPYCDLKADHMCQ-UHFFFAOYSA-N 2-[3-(2-chlorophenoxy)-2-methoxypropyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound N1=C2C=CC(C=3C=CC(OC(F)(F)F)=CC=3)=CN2C(=O)N1CC(OC)COC1=CC=CC=C1Cl YWPYCDLKADHMCQ-UHFFFAOYSA-N 0.000 claims description 7
• MNQWJFACOLCNSA-UHFFFAOYSA-N 2-[3-(4-fluoro-3-pyridin-3-ylphenyl)propyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=C(C=2C=NC=CC=2)C(F)=CC=C1CCCN(C(N1C=2)=O)N=C1C=CC=2C1=CC=C(OC(F)(F)F)C=C1 MNQWJFACOLCNSA-UHFFFAOYSA-N 0.000 claims description 7
• YYVTXNGSGPIDDN-UHFFFAOYSA-N 2-[3-[4-fluoro-3-(1,3-oxazol-2-yl)phenyl]propyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=C(C=2OC=CN=2)C(F)=CC=C1CCCN(C(N1C=2)=O)N=C1C=CC=2C1=CC=C(OC(F)(F)F)C=C1 YYVTXNGSGPIDDN-UHFFFAOYSA-N 0.000 claims description 7
• KETWVEPWCQNJBR-UHFFFAOYSA-N 2-methyl-6-[4-(trifluoromethyl)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C=1N2C(=O)N(C)N=C2C=CC=1C1=CC=C(C(F)(F)F)C=C1 KETWVEPWCQNJBR-UHFFFAOYSA-N 0.000 claims description 7
• FIMNQKPVOLWTCX-UHFFFAOYSA-N 2-propan-2-yl-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C=1N2C(=O)N(C(C)C)N=C2C=CC=1C1=CC=C(OC(F)(F)F)C=C1 FIMNQKPVOLWTCX-UHFFFAOYSA-N 0.000 claims description 7
• UTIFATCBAZTAGS-UHFFFAOYSA-N 5-methyl-2-[(3-methyl-1,2,4-oxadiazol-5-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CC1=NOC(CN2C(N3C(C)=C(C=4C=CC(OC(F)(F)F)=CC=4)C=CC3=N2)=O)=N1 UTIFATCBAZTAGS-UHFFFAOYSA-N 0.000 claims description 7
• FZHYZEQARYMTOK-UHFFFAOYSA-N 8-methyl-6-[4-(trifluoromethoxy)phenyl]-2h-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C=1N(C(NN=2)=O)C=2C(C)=CC=1C1=CC=C(OC(F)(F)F)C=C1 FZHYZEQARYMTOK-UHFFFAOYSA-N 0.000 claims description 7
• 208000007718 Stable Angina Diseases 0.000 claims description 7
• 208000021156 intermittent vascular claudication Diseases 0.000 claims description 7
• 208000010125 myocardial infarction Diseases 0.000 claims description 7
• YWZABFQZZGSQEQ-UHFFFAOYSA-N 2-(1,3-oxazol-2-ylmethyl)-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CC=3OC=CN=3)N=C2C=C1 YWZABFQZZGSQEQ-UHFFFAOYSA-N 0.000 claims description 6
• XOBKXZRZGDWUJA-UHFFFAOYSA-N 2-(2,2,2-trifluoroethyl)-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C=1N2C(=O)N(CC(F)(F)F)N=C2C=CC=1C1=CC=C(OC(F)(F)F)C=C1 XOBKXZRZGDWUJA-UHFFFAOYSA-N 0.000 claims description 6
• HALIVDNAXHLUSG-UHFFFAOYSA-N 2-(2-phenoxyethyl)-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCOC=3C=CC=CC=3)N=C2C=C1 HALIVDNAXHLUSG-UHFFFAOYSA-N 0.000 claims description 6
• VECCJOMKYSSSIJ-UHFFFAOYSA-N 2-(2-pyridin-2-ylethyl)-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCC=3N=CC=CC=3)N=C2C=C1 VECCJOMKYSSSIJ-UHFFFAOYSA-N 0.000 claims description 6
• KPSXKNBCIVEAPH-UHFFFAOYSA-N 2-(2-pyridin-2-yloxyethyl)-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCOC=3N=CC=CC=3)N=C2C=C1 KPSXKNBCIVEAPH-UHFFFAOYSA-N 0.000 claims description 6
• PJVYPBAXQIZBSD-UHFFFAOYSA-N 2-[2-(3-bromopyridin-2-yl)ethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCC=3C(=CC=CN=3)Br)N=C2C=C1 PJVYPBAXQIZBSD-UHFFFAOYSA-N 0.000 claims description 6
• PQXDNFUGLLOROY-UHFFFAOYSA-N 2-[2-(4-ethoxypyrimidin-2-yl)oxyethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CCOC1=CC=NC(OCCN2C(N3C=C(C=CC3=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=N1 PQXDNFUGLLOROY-UHFFFAOYSA-N 0.000 claims description 6
• OITOPVWUINLSRU-UHFFFAOYSA-N 2-[2-(4-fluorophenoxy)ethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(F)=CC=C1OCCN1C(=O)N2C=C(C=3C=CC(OC(F)(F)F)=CC=3)C=CC2=N1 OITOPVWUINLSRU-UHFFFAOYSA-N 0.000 claims description 6
• HUBJVWKMELYCDJ-UHFFFAOYSA-N 2-[2-(5-fluoropyrimidin-2-yl)oxyethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound N1=CC(F)=CN=C1OCCN1C(=O)N2C=C(C=3C=CC(OC(F)(F)F)=CC=3)C=CC2=N1 HUBJVWKMELYCDJ-UHFFFAOYSA-N 0.000 claims description 6
• WRXIIYJRDJHWJX-UHFFFAOYSA-N 2-[2-(6-methoxypyridin-2-yl)ethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound COC1=CC=CC(CCN2C(N3C=C(C=CC3=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=N1 WRXIIYJRDJHWJX-UHFFFAOYSA-N 0.000 claims description 6
• FSYNSILTXXDMQJ-UHFFFAOYSA-N 2-[2-hydroxy-3-(2-methoxyphenoxy)propyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound COC1=CC=CC=C1OCC(O)CN1C(=O)N2C=C(C=3C=CC(OC(F)(F)F)=CC=3)C=CC2=N1 FSYNSILTXXDMQJ-UHFFFAOYSA-N 0.000 claims description 6
• YLDVOFIKASMXON-UHFFFAOYSA-N 2-[3-(2-chlorophenoxy)-2-pyrimidin-2-yloxypropyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CC(COC=3C(=CC=CC=3)Cl)OC=3N=CC=CN=3)N=C2C=C1 YLDVOFIKASMXON-UHFFFAOYSA-N 0.000 claims description 6
• OGLVRRGTKNGIOF-UHFFFAOYSA-N 2-pyridin-2-yl-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(C=3N=CC=CC=3)N=C2C=C1 OGLVRRGTKNGIOF-UHFFFAOYSA-N 0.000 claims description 6
• 208000003037 Diastolic Heart Failure Diseases 0.000 claims description 6
• 125000005605 benzo group Chemical group 0.000 claims description 6
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
• OVXHQIODPLLPGS-UHFFFAOYSA-N 2-(2-hydroxy-3-phenoxypropyl)-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound N1=C2C=CC(C=3C=CC(OC(F)(F)F)=CC=3)=CN2C(=O)N1CC(O)COC1=CC=CC=C1 OVXHQIODPLLPGS-UHFFFAOYSA-N 0.000 claims description 5
• JPLBWJUVLUAHER-UHFFFAOYSA-N 2-(2-pyrazin-2-ylethyl)-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCC=3N=CC=NC=3)N=C2C=C1 JPLBWJUVLUAHER-UHFFFAOYSA-N 0.000 claims description 5
• VQMSMAKRFVGWKP-UHFFFAOYSA-N 2-(2-pyrazol-1-ylethyl)-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCN3N=CC=C3)N=C2C=C1 VQMSMAKRFVGWKP-UHFFFAOYSA-N 0.000 claims description 5
• NJSCGQIPYJCGEK-UHFFFAOYSA-N 2-(2-pyridin-3-ylethyl)-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCC=3C=NC=CC=3)N=C2C=C1 NJSCGQIPYJCGEK-UHFFFAOYSA-N 0.000 claims description 5
• HCIVEOQQCFYJPE-UHFFFAOYSA-N 2-(2-pyrimidin-2-ylethyl)-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCC=3N=CC=CN=3)N=C2C=C1 HCIVEOQQCFYJPE-UHFFFAOYSA-N 0.000 claims description 5
• BCMKIAFOKMLLCY-UHFFFAOYSA-N 2-(2-pyrimidin-4-ylethyl)-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCC=3N=CN=CC=3)N=C2C=C1 BCMKIAFOKMLLCY-UHFFFAOYSA-N 0.000 claims description 5
• LVDLJZHEVASLAG-UHFFFAOYSA-N 2-(2-pyrrolo[1,2-a]pyrazin-1-yloxyethyl)-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCOC=3C4=CC=CN4C=CN=3)N=C2C=C1 LVDLJZHEVASLAG-UHFFFAOYSA-N 0.000 claims description 5
• OSQKXFGNSNWFOT-UHFFFAOYSA-N 2-(3,4-dihydro-2h-chromen-2-ylmethyl)-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CC3OC4=CC=CC=C4CC3)N=C2C=C1 OSQKXFGNSNWFOT-UHFFFAOYSA-N 0.000 claims description 5
• JOABKTNOERGASJ-UHFFFAOYSA-N 2-(pyridin-2-ylmethyl)-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CC=3N=CC=CC=3)N=C2C=C1 JOABKTNOERGASJ-UHFFFAOYSA-N 0.000 claims description 5
• RAKGMCRBTMCOED-UHFFFAOYSA-N 2-[1-(3-ethyl-1,2,4-oxadiazol-5-yl)ethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CCC1=NOC(C(C)N2C(N3C=C(C=CC3=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=N1 RAKGMCRBTMCOED-UHFFFAOYSA-N 0.000 claims description 5
• XGDHSJGDFPOONA-UHFFFAOYSA-N 2-[2-(1-methylbenzimidazol-2-yl)ethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound N=1C2=CC=CC=C2N(C)C=1CCN(C(N1C=2)=O)N=C1C=CC=2C1=CC=C(OC(F)(F)F)C=C1 XGDHSJGDFPOONA-UHFFFAOYSA-N 0.000 claims description 5
• MABLDYZQBQZFDM-UHFFFAOYSA-N 2-[2-(2,6-dimethylphenoxy)ethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CC1=CC=CC(C)=C1OCCN1C(=O)N2C=C(C=3C=CC(OC(F)(F)F)=CC=3)C=CC2=N1 MABLDYZQBQZFDM-UHFFFAOYSA-N 0.000 claims description 5
• LCYDBKHIAPRFCQ-UHFFFAOYSA-N 2-[2-(3-chlorophenoxy)ethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCOC=3C=C(Cl)C=CC=3)N=C2C=C1 LCYDBKHIAPRFCQ-UHFFFAOYSA-N 0.000 claims description 5
• NJUWJIRXCMEKIJ-UHFFFAOYSA-N 2-[2-(3-methylpyrazol-1-yl)ethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound N1=C(C)C=CN1CCN1C(=O)N2C=C(C=3C=CC(OC(F)(F)F)=CC=3)C=CC2=N1 NJUWJIRXCMEKIJ-UHFFFAOYSA-N 0.000 claims description 5
• RVEZVRQDJRMSLZ-UHFFFAOYSA-N 2-[2-(3-methylpyridin-2-yl)ethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CC1=CC=CN=C1CCN1C(=O)N2C=C(C=3C=CC(OC(F)(F)F)=CC=3)C=CC2=N1 RVEZVRQDJRMSLZ-UHFFFAOYSA-N 0.000 claims description 5
• GRULTNVOGICNDD-UHFFFAOYSA-N 2-[2-(4,4-difluoropiperidin-1-yl)ethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCN3CCC(F)(F)CC3)N=C2C=C1 GRULTNVOGICNDD-UHFFFAOYSA-N 0.000 claims description 5
• CWLUOIISRZUKND-UHFFFAOYSA-N 2-[2-(4-cyclopropylpyridin-2-yl)ethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCC=3N=CC=C(C=3)C3CC3)N=C2C=C1 CWLUOIISRZUKND-UHFFFAOYSA-N 0.000 claims description 5
• PBOLJUHFEBCLEW-UHFFFAOYSA-N 2-[2-(5-chloro-4-methoxypyrimidin-2-yl)oxyethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=C(Cl)C(OC)=NC(OCCN2C(N3C=C(C=CC3=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=N1 PBOLJUHFEBCLEW-UHFFFAOYSA-N 0.000 claims description 5
• FDGAKDDEXYYGQQ-UHFFFAOYSA-N 2-[2-(6-methylpyridin-2-yl)ethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CC1=CC=CC(CCN2C(N3C=C(C=CC3=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=N1 FDGAKDDEXYYGQQ-UHFFFAOYSA-N 0.000 claims description 5
• NNXWYNPCXFMLPG-UHFFFAOYSA-N 2-[2-[(5-methyl-1,2,4-oxadiazol-3-yl)methoxy]ethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound O1C(C)=NC(COCCN2C(N3C=C(C=CC3=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=N1 NNXWYNPCXFMLPG-UHFFFAOYSA-N 0.000 claims description 5
• YBXKMLYTHQBHJQ-UHFFFAOYSA-N 2-[2-[2-(3-methyl-1,2,4-oxadiazol-5-yl)phenoxy]ethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CC1=NOC(C=2C(=CC=CC=2)OCCN2C(N3C=C(C=CC3=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=N1 YBXKMLYTHQBHJQ-UHFFFAOYSA-N 0.000 claims description 5
• CKSVRMWEVBWXQA-UHFFFAOYSA-N 2-[3-(2-chlorophenoxy)propyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCCOC=3C(=CC=CC=3)Cl)N=C2C=C1 CKSVRMWEVBWXQA-UHFFFAOYSA-N 0.000 claims description 5
• NMNPYFYTKLISDF-UHFFFAOYSA-N 2-[3-(2-methoxyphenoxy)propyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound COC1=CC=CC=C1OCCCN1C(=O)N2C=C(C=3C=CC(OC(F)(F)F)=CC=3)C=CC2=N1 NMNPYFYTKLISDF-UHFFFAOYSA-N 0.000 claims description 5
• LOZNQJGOYFAIMZ-UHFFFAOYSA-N 2-[3-(4,5-dichloro-2-methoxyphenoxy)-2-hydroxypropyl]-6-[4-(trifluoromethyl)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound COC1=CC(Cl)=C(Cl)C=C1OCC(O)CN1C(=O)N2C=C(C=3C=CC(=CC=3)C(F)(F)F)C=CC2=N1 LOZNQJGOYFAIMZ-UHFFFAOYSA-N 0.000 claims description 5
• RFAFLCQWYNPTOU-UHFFFAOYSA-N 2-[3-(4-chlorophenoxy)-2-hydroxypropyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound N1=C2C=CC(C=3C=CC(OC(F)(F)F)=CC=3)=CN2C(=O)N1CC(O)COC1=CC=C(Cl)C=C1 RFAFLCQWYNPTOU-UHFFFAOYSA-N 0.000 claims description 5
• SXPRBFVBXBOHMC-UHFFFAOYSA-N 2-[3-(4-fluoro-2-methoxyphenoxy)propyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound COC1=CC(F)=CC=C1OCCCN1C(=O)N2C=C(C=3C=CC(OC(F)(F)F)=CC=3)C=CC2=N1 SXPRBFVBXBOHMC-UHFFFAOYSA-N 0.000 claims description 5
• BJGKPGUAWQJOTA-UHFFFAOYSA-N 2-[3-[3-oxo-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-2-yl]propoxy]benzonitrile Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCCOC=3C(=CC=CC=3)C#N)N=C2C=C1 BJGKPGUAWQJOTA-UHFFFAOYSA-N 0.000 claims description 5
• YEURUVYSYMOYEU-UHFFFAOYSA-N 2-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound FC(OC1=CC=C(C=C1)N1N=C2N(C=CC=C2)C1=O)(F)F YEURUVYSYMOYEU-UHFFFAOYSA-N 0.000 claims description 5
• SSJXLMOUGLZTRT-UHFFFAOYSA-N 5-methoxy-2-[(3-methyl-1,2,4-oxadiazol-5-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound O=C1N2C(OC)=C(C=3C=CC(OC(F)(F)F)=CC=3)C=CC2=NN1CC1=NC(C)=NO1 SSJXLMOUGLZTRT-UHFFFAOYSA-N 0.000 claims description 5
• 206010007556 Cardiac failure acute Diseases 0.000 claims description 5
• 208000008253 Systolic Heart Failure Diseases 0.000 claims description 5
• 206010015037 epilepsy Diseases 0.000 claims description 5
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
• 208000002815 pulmonary hypertension Diseases 0.000 claims description 5
• 230000000306 recurrent effect Effects 0.000 claims description 5
• LJSSRJKRLOGJFW-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-ylmethyl)-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CC=3SC4=CC=CC=C4N=3)N=C2C=C1 LJSSRJKRLOGJFW-UHFFFAOYSA-N 0.000 claims description 4
• FGLZQEQLYKFHCZ-UHFFFAOYSA-N 2-(2-pyridazin-3-yloxyethyl)-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCOC=3N=NC=CC=3)N=C2C=C1 FGLZQEQLYKFHCZ-UHFFFAOYSA-N 0.000 claims description 4
• VONZHFWGMKSOPA-UHFFFAOYSA-N 2-[2-(2,6-difluorophenyl)ethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound FC1=CC=CC(F)=C1CCN1C(=O)N2C=C(C=3C=CC(OC(F)(F)F)=CC=3)C=CC2=N1 VONZHFWGMKSOPA-UHFFFAOYSA-N 0.000 claims description 4
• ZIGOLNNMIVNRON-UHFFFAOYSA-N 2-[2-(2-chloropyrimidin-5-yl)oxyethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCOC=3C=NC(Cl)=NC=3)N=C2C=C1 ZIGOLNNMIVNRON-UHFFFAOYSA-N 0.000 claims description 4
• ZTYBMLCVOOCLLE-UHFFFAOYSA-N 2-[2-(2-methoxyphenoxy)ethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound COC1=CC=CC=C1OCCN1C(=O)N2C=C(C=3C=CC(OC(F)(F)F)=CC=3)C=CC2=N1 ZTYBMLCVOOCLLE-UHFFFAOYSA-N 0.000 claims description 4
• LZSOSYDZFDNSHU-UHFFFAOYSA-N 2-[2-(2-oxo-3-phenoxypyrrolidin-1-yl)ethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCN3C(C(OC=4C=CC=CC=4)CC3)=O)N=C2C=C1 LZSOSYDZFDNSHU-UHFFFAOYSA-N 0.000 claims description 4
• YZYPKNNBTUSEAI-UHFFFAOYSA-N 2-[2-(3-bromo-6-methoxypyridin-2-yl)ethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound COC1=CC=C(Br)C(CCN2C(N3C=C(C=CC3=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=N1 YZYPKNNBTUSEAI-UHFFFAOYSA-N 0.000 claims description 4
• MFCRZFOKCWGDLN-UHFFFAOYSA-N 2-[2-(3-cyclopropylpyridin-2-yl)ethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCC=3C(=CC=CN=3)C3CC3)N=C2C=C1 MFCRZFOKCWGDLN-UHFFFAOYSA-N 0.000 claims description 4
• HCNSGWVLGRSJRT-UHFFFAOYSA-N 2-[2-(3-phenoxypyrrolidin-1-yl)ethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCN3CC(CC3)OC=3C=CC=CC=3)N=C2C=C1 HCNSGWVLGRSJRT-UHFFFAOYSA-N 0.000 claims description 4
• BIDPHMBOBGPSFW-UHFFFAOYSA-N 2-[2-(4-chloropyrazol-1-yl)ethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCN3N=CC(Cl)=C3)N=C2C=C1 BIDPHMBOBGPSFW-UHFFFAOYSA-N 0.000 claims description 4
• LMWZUQQEPACYHL-UHFFFAOYSA-N 2-[2-(4-methylsulfanylpyrimidin-2-yl)oxyethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CSC1=CC=NC(OCCN2C(N3C=C(C=CC3=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=N1 LMWZUQQEPACYHL-UHFFFAOYSA-N 0.000 claims description 4
• HROAXNIKKKJMJR-UHFFFAOYSA-N 2-[2-(4-phenylimidazol-1-yl)ethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCN3C=C(N=C3)C=3C=CC=CC=3)N=C2C=C1 HROAXNIKKKJMJR-UHFFFAOYSA-N 0.000 claims description 4
• GUGCDVSZLLAGEO-UHFFFAOYSA-N 2-[2-(4-propan-2-yloxypyrimidin-2-yl)oxyethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CC(C)OC1=CC=NC(OCCN2C(N3C=C(C=CC3=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=N1 GUGCDVSZLLAGEO-UHFFFAOYSA-N 0.000 claims description 4
• ORVBSGIBHXQPGV-UHFFFAOYSA-N 2-[2-(5-chloropyrimidin-2-yl)oxyethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCOC=3N=CC(Cl)=CN=3)N=C2C=C1 ORVBSGIBHXQPGV-UHFFFAOYSA-N 0.000 claims description 4
• CHMUARBBRQXVIR-UHFFFAOYSA-N 2-[2-(5-methylpyrimidin-2-yl)oxyethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound N1=CC(C)=CN=C1OCCN1C(=O)N2C=C(C=3C=CC(OC(F)(F)F)=CC=3)C=CC2=N1 CHMUARBBRQXVIR-UHFFFAOYSA-N 0.000 claims description 4
• FIUJLHZTQNKDDW-UHFFFAOYSA-N 2-[2-[4-(2,2,2-trifluoroethoxy)pyrimidin-2-yl]oxyethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound FC(F)(F)COC1=CC=NC(OCCN2C(N3C=C(C=CC3=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=N1 FIUJLHZTQNKDDW-UHFFFAOYSA-N 0.000 claims description 4
• WJAPRRQAVZDFOB-UHFFFAOYSA-N 2-[2-[4-(cyclopropylmethoxy)pyrimidin-2-yl]oxyethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCOC=3N=C(OCC4CC4)C=CN=3)N=C2C=C1 WJAPRRQAVZDFOB-UHFFFAOYSA-N 0.000 claims description 4
• WVTQLJBWCSRDMW-UHFFFAOYSA-N 2-[2-hydroxy-3-(2-propan-2-yloxyphenoxy)propyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CC(C)OC1=CC=CC=C1OCC(O)CN1C(=O)N2C=C(C=3C=CC(OC(F)(F)F)=CC=3)C=CC2=N1 WVTQLJBWCSRDMW-UHFFFAOYSA-N 0.000 claims description 4
• CFZZBGFEIPOQTD-UHFFFAOYSA-N 2-[2-methoxy-3-(2-methoxyphenoxy)propyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound N1=C2C=CC(C=3C=CC(OC(F)(F)F)=CC=3)=CN2C(=O)N1CC(OC)COC1=CC=CC=C1OC CFZZBGFEIPOQTD-UHFFFAOYSA-N 0.000 claims description 4
• RSIBUGZZQAVBOM-UHFFFAOYSA-N 2-[3-(4-fluoro-2-methoxyphenoxy)-2-hydroxypropyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound COC1=CC(F)=CC=C1OCC(O)CN1C(=O)N2C=C(C=3C=CC(OC(F)(F)F)=CC=3)C=CC2=N1 RSIBUGZZQAVBOM-UHFFFAOYSA-N 0.000 claims description 4
• JRDZTUMYLTXQDP-UHFFFAOYSA-N 2-[3-(4-fluoro-2-methoxyphenoxy)-2-methoxypropyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound N1=C2C=CC(C=3C=CC(OC(F)(F)F)=CC=3)=CN2C(=O)N1CC(OC)COC1=CC=C(F)C=C1OC JRDZTUMYLTXQDP-UHFFFAOYSA-N 0.000 claims description 4
• MNDYBFMGLXVTSQ-OAHLLOKOSA-N 2-[[5-[(4r)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,2,4-oxadiazol-3-yl]methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound O1C(C)(C)OC[C@@H]1C1=NC(CN2C(N3C=C(C=CC3=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=NO1 MNDYBFMGLXVTSQ-OAHLLOKOSA-N 0.000 claims description 4
• IBYNBIZYZJFITL-UHFFFAOYSA-N 6-[4-(trifluoromethoxy)phenyl]-2-[[4-(trifluoromethoxy)phenyl]methyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1CN1C(=O)N2C=C(C=3C=CC(OC(F)(F)F)=CC=3)C=CC2=N1 IBYNBIZYZJFITL-UHFFFAOYSA-N 0.000 claims description 4
• 208000004476 Acute Coronary Syndrome Diseases 0.000 claims description 4
• 206010003130 Arrhythmia supraventricular Diseases 0.000 claims description 4
• 206010010904 Convulsion Diseases 0.000 claims description 4
• 208000032131 Diabetic Neuropathies Diseases 0.000 claims description 4
• 206010033799 Paralysis Diseases 0.000 claims description 4
• 206010047281 Ventricular arrhythmia Diseases 0.000 claims description 4
• 208000004296 neuralgia Diseases 0.000 claims description 4
• 208000021722 neuropathic pain Diseases 0.000 claims description 4
• 230000002093 peripheral effect Effects 0.000 claims description 4
• SIASCGMZXFPZNB-UHFFFAOYSA-N 2-(3-phenylprop-2-enyl)-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CC=CC=3C=CC=CC=3)N=C2C=C1 SIASCGMZXFPZNB-UHFFFAOYSA-N 0.000 claims description 3
• RIONBHYBBHCCBB-UHFFFAOYSA-N 2-(3-pyridazin-3-yloxypropyl)-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCCOC=3N=NC=CC=3)N=C2C=C1 RIONBHYBBHCCBB-UHFFFAOYSA-N 0.000 claims description 3
• YFLRCGNFZGDKJZ-QGZVFWFLSA-N 2-[(2r)-3-methoxy-2-[3-(trifluoromethyl)pyridin-2-yl]oxypropyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C([C@H](COC)OC=1C(=CC=CN=1)C(F)(F)F)N(C(N1C=2)=O)N=C1C=CC=2C1=CC=C(OC(F)(F)F)C=C1 YFLRCGNFZGDKJZ-QGZVFWFLSA-N 0.000 claims description 3
• GJCXAVXCYWJLBZ-UHFFFAOYSA-N 2-[2-(4-phenylpyrimidin-2-yl)oxyethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCOC=3N=C(C=CN=3)C=3C=CC=CC=3)N=C2C=C1 GJCXAVXCYWJLBZ-UHFFFAOYSA-N 0.000 claims description 3
• YXIXQPPNKVUIRT-UHFFFAOYSA-N 2-[2-(5-pyridin-3-ylpyridin-2-yl)ethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCC=3N=CC(=CC=3)C=3C=NC=CC=3)N=C2C=C1 YXIXQPPNKVUIRT-UHFFFAOYSA-N 0.000 claims description 3
• WTMYCPDFCNVZDW-UHFFFAOYSA-N 2-[2-[3-oxo-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-2-yl]ethoxy]pyrimidine-4-carbonitrile Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCOC=3N=C(C=CN=3)C#N)N=C2C=C1 WTMYCPDFCNVZDW-UHFFFAOYSA-N 0.000 claims description 3
• OMPOZZVWEMYHAA-UHFFFAOYSA-N 2-[2-[4-(3,3-difluoroazetidin-1-yl)-5-fluoropyrimidin-2-yl]oxyethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound N1=C(N2CC(F)(F)C2)C(F)=CN=C1OCCN(C(N1C=2)=O)N=C1C=CC=2C1=CC=C(OC(F)(F)F)C=C1 OMPOZZVWEMYHAA-UHFFFAOYSA-N 0.000 claims description 3
• VOGMJXDGKJVSMN-UHFFFAOYSA-N 2-[3-(2-ethoxyphenoxy)-2-hydroxypropyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CCOC1=CC=CC=C1OCC(O)CN1C(=O)N2C=C(C=3C=CC(OC(F)(F)F)=CC=3)C=CC2=N1 VOGMJXDGKJVSMN-UHFFFAOYSA-N 0.000 claims description 3
• JBKYHZVKJXFZMX-UHFFFAOYSA-N 2-[3-(2-fluorophenoxy)propyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound FC1=CC=CC=C1OCCCN1C(=O)N2C=C(C=3C=CC(OC(F)(F)F)=CC=3)C=CC2=N1 JBKYHZVKJXFZMX-UHFFFAOYSA-N 0.000 claims description 3
• ITHFAPIQRKNGQT-UHFFFAOYSA-N 2-[3-(3-bromo-4-fluorophenyl)propyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=C(Br)C(F)=CC=C1CCCN1C(=O)N2C=C(C=3C=CC(OC(F)(F)F)=CC=3)C=CC2=N1 ITHFAPIQRKNGQT-UHFFFAOYSA-N 0.000 claims description 3
• KZGAUBIJVIHXTL-UHFFFAOYSA-N 2-[3-(4-fluorophenyl)propyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(F)=CC=C1CCCN1C(=O)N2C=C(C=3C=CC(OC(F)(F)F)=CC=3)C=CC2=N1 KZGAUBIJVIHXTL-UHFFFAOYSA-N 0.000 claims description 3
• NELTZKZPWSUPCT-UHFFFAOYSA-N 2-[4-(4-ethoxypyrimidin-2-yl)oxyoxolan-3-yl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CCOC1=CC=NC(OC2C(COC2)N2C(N3C=C(C=CC3=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=N1 NELTZKZPWSUPCT-UHFFFAOYSA-N 0.000 claims description 3
• QDZLZRMPIKXWGV-UHFFFAOYSA-N 2-[4-(trifluoromethyl)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound FC(C1=CC=C(C=C1)N1N=C2N(C=CC=C2)C1=O)(F)F QDZLZRMPIKXWGV-UHFFFAOYSA-N 0.000 claims description 3
• WJWGCBXJYLKGEI-UHFFFAOYSA-N 2-(2-isoquinolin-1-yloxyethyl)-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCOC=3C4=CC=CC=C4C=CN=3)N=C2C=C1 WJWGCBXJYLKGEI-UHFFFAOYSA-N 0.000 claims description 2
• AVBIQOMJIYFZHZ-UHFFFAOYSA-N 2-[2-(2,4-difluorophenyl)ethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound FC1=CC(F)=CC=C1CCN1C(=O)N2C=C(C=3C=CC(OC(F)(F)F)=CC=3)C=CC2=N1 AVBIQOMJIYFZHZ-UHFFFAOYSA-N 0.000 claims description 2
• WIJCIFKHSGPZJO-UHFFFAOYSA-N 2-[2-(4-chlorophenoxy)ethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCOC=3C=CC(Cl)=CC=3)N=C2C=C1 WIJCIFKHSGPZJO-UHFFFAOYSA-N 0.000 claims description 2
• KOWDLMAZRSOJHC-UHFFFAOYSA-N 2-[2-[2-[3-oxo-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-2-yl]ethoxy]pyrimidin-4-yl]oxyacetonitrile Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCOC=3N=C(OCC#N)C=CN=3)N=C2C=C1 KOWDLMAZRSOJHC-UHFFFAOYSA-N 0.000 claims description 2
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
• 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 2
• SIJBDWPVNAYVGY-UHFFFAOYSA-N 2,2-dimethyl-1,3-dioxolane Chemical compound CC1(C)OCCO1 SIJBDWPVNAYVGY-UHFFFAOYSA-N 0.000 claims 1
• JIADELSANNMYFC-UHFFFAOYSA-N 5-methoxypyrimidine Chemical compound COC1=CN=CN=C1 JIADELSANNMYFC-UHFFFAOYSA-N 0.000 claims 1
• 208000027418 Wounds and injury Diseases 0.000 claims 1
• 230000006378 damage Effects 0.000 claims 1
• 208000014674 injury Diseases 0.000 claims 1
• 230000010410 reperfusion Effects 0.000 claims 1
• 125000005843 halogen group Chemical group 0.000 abstract description 50
• 239000000203 mixture Substances 0.000 description 83
• 239000002585 base Substances 0.000 description 79
• 210000004027 cell Anatomy 0.000 description 73
• 239000000243 solution Substances 0.000 description 62
• 238000012360 testing method Methods 0.000 description 48
• 230000000694 effects Effects 0.000 description 45
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 38
• 238000005481 NMR spectroscopy Methods 0.000 description 34
• 239000003814 drug Substances 0.000 description 34
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 34
• 108091006146 Channels Proteins 0.000 description 30
• 238000006243 chemical reaction Methods 0.000 description 30
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 29
• 239000002904 solvent Substances 0.000 description 28
• 229940124597 therapeutic agent Drugs 0.000 description 27
• 229910052736 halogen Inorganic materials 0.000 description 26
• 150000002367 halogens Chemical class 0.000 description 26
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 25
• 238000007792 addition Methods 0.000 description 24
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
• 125000000392 cycloalkenyl group Chemical group 0.000 description 23
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 22
• 230000000052 comparative effect Effects 0.000 description 22
• WCKSPUOMUKLNAH-UHFFFAOYSA-N 6-[4-(trifluoromethoxy)phenyl]-2h-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)NN=C2C=C1 WCKSPUOMUKLNAH-UHFFFAOYSA-N 0.000 description 21
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
• 239000003195 sodium channel blocking agent Substances 0.000 description 21
• 239000003826 tablet Substances 0.000 description 21
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
• 150000001412 amines Chemical class 0.000 description 19
• 239000004615 ingredient Substances 0.000 description 19
• TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 18
• 238000003556 assay Methods 0.000 description 18
• 125000004432 carbon atom Chemical group C* 0.000 description 18
• 230000000638 stimulation Effects 0.000 description 18
• 238000005160 1H NMR spectroscopy Methods 0.000 description 17
• 229910000027 potassium carbonate Inorganic materials 0.000 description 17
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 16
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
• 125000004429 atom Chemical group 0.000 description 16
• 235000019439 ethyl acetate Nutrition 0.000 description 16
• CFMYXEVWODSLAX-QOZOJKKESA-N tetrodotoxin Chemical compound O([C@@]([C@H]1O)(O)O[C@H]2[C@@]3(O)CO)[C@H]3[C@@H](O)[C@]11[C@H]2[C@@H](O)N=C(N)N1 CFMYXEVWODSLAX-QOZOJKKESA-N 0.000 description 16
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 15
• 239000003153 chemical reaction reagent Substances 0.000 description 15
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 15
• 239000000047 product Substances 0.000 description 15
• 229950010357 tetrodotoxin Drugs 0.000 description 15
• CFMYXEVWODSLAX-UHFFFAOYSA-N tetrodotoxin Natural products C12C(O)NC(=N)NC2(C2O)C(O)C3C(CO)(O)C1OC2(O)O3 CFMYXEVWODSLAX-UHFFFAOYSA-N 0.000 description 15
• 239000004480 active ingredient Substances 0.000 description 14
• 239000013543 active substance Substances 0.000 description 14
• 210000002216 heart Anatomy 0.000 description 14
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 14
• JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 13
• 239000007995 HEPES buffer Substances 0.000 description 13
• XKLMZUWKNUAPSZ-UHFFFAOYSA-N N-(2,6-dimethylphenyl)-2-{4-[2-hydroxy-3-(2-methoxyphenoxy)propyl]piperazin-1-yl}acetamide Chemical compound COC1=CC=CC=C1OCC(O)CN1CCN(CC(=O)NC=2C(=CC=CC=2C)C)CC1 XKLMZUWKNUAPSZ-UHFFFAOYSA-N 0.000 description 13
• 125000002947 alkylene group Chemical group 0.000 description 13
• 201000010099 disease Diseases 0.000 description 13
• 238000012423 maintenance Methods 0.000 description 13
• 239000000843 powder Substances 0.000 description 13
• 239000007787 solid Substances 0.000 description 13
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 12
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
• 125000005110 aryl thio group Chemical group 0.000 description 12
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 12
• 239000012044 organic layer Substances 0.000 description 12
• 235000011181 potassium carbonates Nutrition 0.000 description 12
• 238000003786 synthesis reaction Methods 0.000 description 12
• 125000004442 acylamino group Chemical group 0.000 description 11
• 125000004423 acyloxy group Chemical group 0.000 description 11
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 11
• 125000005553 heteroaryloxy group Chemical group 0.000 description 11
• 125000004470 heterocyclooxy group Chemical group 0.000 description 11
• 238000002360 preparation method Methods 0.000 description 11
• 229960000213 ranolazine Drugs 0.000 description 11
• 230000009467 reduction Effects 0.000 description 11
• 230000002829 reductive effect Effects 0.000 description 11
• 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 11
• 125000000033 alkoxyamino group Chemical group 0.000 description 10
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 10
• 125000006598 aminocarbonylamino group Chemical group 0.000 description 10
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 10
• 125000005368 heteroarylthio group Chemical group 0.000 description 10
• 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 description 10
• 238000012216 screening Methods 0.000 description 10
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 10
• 239000003242 anti bacterial agent Substances 0.000 description 9
• 230000015572 biosynthetic process Effects 0.000 description 9
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 9
• 230000001419 dependent effect Effects 0.000 description 9
• 230000006870 function Effects 0.000 description 9
• 229910001629 magnesium chloride Inorganic materials 0.000 description 9
• 239000012528 membrane Substances 0.000 description 9
• 239000007858 starting material Substances 0.000 description 9
• 239000011550 stock solution Substances 0.000 description 9
• 125000003107 substituted aryl group Chemical group 0.000 description 9
• 239000000725 suspension Substances 0.000 description 9
• SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 description 8
• 125000004414 alkyl thio group Chemical group 0.000 description 8
• 238000004458 analytical method Methods 0.000 description 8
• 230000008901 benefit Effects 0.000 description 8
• 239000012267 brine Substances 0.000 description 8
• 238000009472 formulation Methods 0.000 description 8
• 239000001963 growth medium Substances 0.000 description 8
• 125000004468 heterocyclylthio group Chemical group 0.000 description 8
• 230000002779 inactivation Effects 0.000 description 8
• 230000010412 perfusion Effects 0.000 description 8
• 230000002085 persistent effect Effects 0.000 description 8
• 235000017557 sodium bicarbonate Nutrition 0.000 description 8
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
• 238000003756 stirring Methods 0.000 description 8
• 230000001256 tonic effect Effects 0.000 description 8
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 7
• UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 7
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
• 101000631760 Homo sapiens Sodium channel protein type 1 subunit alpha Proteins 0.000 description 7
• 101000654386 Homo sapiens Sodium channel protein type 9 subunit alpha Proteins 0.000 description 7
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
• 108090000420 L-Type Calcium Channels Proteins 0.000 description 7
• 102000004016 L-Type Calcium Channels Human genes 0.000 description 7
• 208000019693 Lung disease Diseases 0.000 description 7
• 239000007832 Na2SO4 Substances 0.000 description 7
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
• 229940088710 antibiotic agent Drugs 0.000 description 7
• 239000007864 aqueous solution Substances 0.000 description 7
• 239000002876 beta blocker Substances 0.000 description 7
• 230000000903 blocking effect Effects 0.000 description 7
• 210000004556 brain Anatomy 0.000 description 7
• 239000001110 calcium chloride Substances 0.000 description 7
• 235000011148 calcium chloride Nutrition 0.000 description 7
• 229910001628 calcium chloride Inorganic materials 0.000 description 7
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 7
• 125000004181 carboxyalkyl group Chemical group 0.000 description 7
• 210000000170 cell membrane Anatomy 0.000 description 7
• 239000012043 crude product Substances 0.000 description 7
• 239000013078 crystal Substances 0.000 description 7
• DEFVIWRASFVYLL-UHFFFAOYSA-N ethylene glycol bis(2-aminoethyl)tetraacetic acid Chemical compound OC(=O)CN(CC(O)=O)CCOCCOCCN(CC(O)=O)CC(O)=O DEFVIWRASFVYLL-UHFFFAOYSA-N 0.000 description 7
• 238000004128 high performance liquid chromatography Methods 0.000 description 7
• 239000000463 material Substances 0.000 description 7
• HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 description 7
• 125000006239 protecting group Chemical group 0.000 description 7
• 239000011780 sodium chloride Substances 0.000 description 7
• 229910052938 sodium sulfate Inorganic materials 0.000 description 7
• 235000011152 sodium sulphate Nutrition 0.000 description 7
• 208000024891 symptom Diseases 0.000 description 7
• 150000003573 thiols Chemical class 0.000 description 7
• FINVLTBKFNUEGB-UHFFFAOYSA-N 2-[2-[4-(4-chlorophenoxy)pyrimidin-2-yl]oxyethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCOC=3N=C(OC=4C=CC(Cl)=CC=4)C=CN=3)N=C2C=C1 FINVLTBKFNUEGB-UHFFFAOYSA-N 0.000 description 6
• SGUAFYQXFOLMHL-UHFFFAOYSA-N 2-hydroxy-5-{1-hydroxy-2-[(4-phenylbutan-2-yl)amino]ethyl}benzamide Chemical compound C=1C=C(O)C(C(N)=O)=CC=1C(O)CNC(C)CCC1=CC=CC=C1 SGUAFYQXFOLMHL-UHFFFAOYSA-N 0.000 description 6
• FHOXTMMDQPXGEB-UHFFFAOYSA-N 6-[4-(trifluoromethyl)phenyl]-2h-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CN2C(=O)NN=C2C=C1 FHOXTMMDQPXGEB-UHFFFAOYSA-N 0.000 description 6
• 208000024172 Cardiovascular disease Diseases 0.000 description 6
• GJSURZIOUXUGAL-UHFFFAOYSA-N Clonidine Chemical compound ClC1=CC=CC(Cl)=C1NC1=NCCN1 GJSURZIOUXUGAL-UHFFFAOYSA-N 0.000 description 6
• 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 6
• 208000018522 Gastrointestinal disease Diseases 0.000 description 6
• 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 6
• RPTUSVTUFVMDQK-UHFFFAOYSA-N Hidralazin Chemical compound C1=CC=C2C(NN)=NN=CC2=C1 RPTUSVTUFVMDQK-UHFFFAOYSA-N 0.000 description 6
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 6
• GIYXAJPCNFJEHY-UHFFFAOYSA-N N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]-1-propanamine hydrochloride (1:1) Chemical compound Cl.C=1C=CC=CC=1C(CCNC)OC1=CC=C(C(F)(F)F)C=C1 GIYXAJPCNFJEHY-UHFFFAOYSA-N 0.000 description 6
• 208000002193 Pain Diseases 0.000 description 6
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
• 108010052164 Sodium Channels Proteins 0.000 description 6
• 102000018674 Sodium Channels Human genes 0.000 description 6
• 102100028910 Sodium channel protein type 1 subunit alpha Human genes 0.000 description 6
• 102100031367 Sodium channel protein type 9 subunit alpha Human genes 0.000 description 6
• 229920002472 Starch Polymers 0.000 description 6
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
• 239000002253 acid Substances 0.000 description 6
• 230000004913 activation Effects 0.000 description 6
• 229940035676 analgesics Drugs 0.000 description 6
• 239000000730 antalgic agent Substances 0.000 description 6
• 239000003146 anticoagulant agent Substances 0.000 description 6
• 239000000935 antidepressant agent Substances 0.000 description 6
• 229940005513 antidepressants Drugs 0.000 description 6
• 229940030600 antihypertensive agent Drugs 0.000 description 6
• 239000002220 antihypertensive agent Substances 0.000 description 6
• 239000002249 anxiolytic agent Substances 0.000 description 6
• 230000000949 anxiolytic effect Effects 0.000 description 6
• 229940005530 anxiolytics Drugs 0.000 description 6
• 210000001367 artery Anatomy 0.000 description 6
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
• 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 6
• AIYUHDOJVYHVIT-UHFFFAOYSA-M caesium chloride Chemical compound [Cl-].[Cs+] AIYUHDOJVYHVIT-UHFFFAOYSA-M 0.000 description 6
• 230000000747 cardiac effect Effects 0.000 description 6
• 230000002999 depolarising effect Effects 0.000 description 6
• FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 6
• 229940079593 drug Drugs 0.000 description 6
• FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 6
• BRZYSWJRSDMWLG-CAXSIQPQSA-N geneticin Natural products O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](C(C)O)O2)N)[C@@H](N)C[C@H]1N BRZYSWJRSDMWLG-CAXSIQPQSA-N 0.000 description 6
• 239000011521 glass Substances 0.000 description 6
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
• 235000019359 magnesium stearate Nutrition 0.000 description 6
• 208000030159 metabolic disease Diseases 0.000 description 6
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 6
• 230000004048 modification Effects 0.000 description 6
• 238000012986 modification Methods 0.000 description 6
• 239000001301 oxygen Substances 0.000 description 6
• 229910052760 oxygen Inorganic materials 0.000 description 6
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
• AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 6
• 238000000746 purification Methods 0.000 description 6
• 230000004044 response Effects 0.000 description 6
• PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 6
• 235000019698 starch Nutrition 0.000 description 6
• 230000001225 therapeutic effect Effects 0.000 description 6
• 210000001519 tissue Anatomy 0.000 description 6
• JPBBULQEKZVHQV-UHFFFAOYSA-N 2-(3-phenoxypropyl)-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCCOC=3C=CC=CC=3)N=C2C=C1 JPBBULQEKZVHQV-UHFFFAOYSA-N 0.000 description 5
• YWPYCDLKADHMCQ-GOSISDBHSA-N 2-[(2r)-3-(2-chlorophenoxy)-2-methoxypropyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C([C@H](OC)CN1C(N2C=C(C=CC2=N1)C=1C=CC(OC(F)(F)F)=CC=1)=O)OC1=CC=CC=C1Cl YWPYCDLKADHMCQ-GOSISDBHSA-N 0.000 description 5
• SOPXTTHIOLOJNS-UHFFFAOYSA-N 2-[(3-ethyl-1,2,4-oxadiazol-5-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CCC1=NOC(CN2C(N3C=C(C=CC3=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=N1 SOPXTTHIOLOJNS-UHFFFAOYSA-N 0.000 description 5
• KEJHEWPVIDRSDW-UHFFFAOYSA-N 2-[2-(3-methylpyrazin-2-yl)ethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CC1=NC=CN=C1CCN1C(=O)N2C=C(C=3C=CC(OC(F)(F)F)=CC=3)C=CC2=N1 KEJHEWPVIDRSDW-UHFFFAOYSA-N 0.000 description 5
• 108090000862 Ion Channels Proteins 0.000 description 5
• 108010007859 Lisinopril Proteins 0.000 description 5
• 229920000168 Microcrystalline cellulose Polymers 0.000 description 5
• 102000004257 Potassium Channel Human genes 0.000 description 5
• 239000003416 antiarrhythmic agent Substances 0.000 description 5
• 239000003524 antilipemic agent Substances 0.000 description 5
• 230000006793 arrhythmia Effects 0.000 description 5
• 229940097320 beta blocking agent Drugs 0.000 description 5
• 210000004204 blood vessel Anatomy 0.000 description 5
• 239000002775 capsule Substances 0.000 description 5
• HSUGRBWQSSZJOP-RTWAWAEBSA-N diltiazem Chemical compound C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CCN(C)C)C2=CC=CC=C2S1 HSUGRBWQSSZJOP-RTWAWAEBSA-N 0.000 description 5
• 239000000975 dye Substances 0.000 description 5
• 238000002474 experimental method Methods 0.000 description 5
• 238000001727 in vivo Methods 0.000 description 5
• 239000007788 liquid Substances 0.000 description 5
• CZRQXSDBMCMPNJ-ZUIPZQNBSA-N lisinopril dihydrate Chemical compound O.O.C([C@H](N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(O)=O)C(O)=O)CC1=CC=CC=C1 CZRQXSDBMCMPNJ-ZUIPZQNBSA-N 0.000 description 5
• 235000019813 microcrystalline cellulose Nutrition 0.000 description 5
• 239000008108 microcrystalline cellulose Substances 0.000 description 5
• 229940016286 microcrystalline cellulose Drugs 0.000 description 5
• 239000012299 nitrogen atmosphere Substances 0.000 description 5
• 239000003921 oil Substances 0.000 description 5
• 235000019198 oils Nutrition 0.000 description 5
• 235000015320 potassium carbonate Nutrition 0.000 description 5
• 108020001213 potassium channel Proteins 0.000 description 5
• 239000011541 reaction mixture Substances 0.000 description 5
• 238000011084 recovery Methods 0.000 description 5
• 229930195734 saturated hydrocarbon Natural products 0.000 description 5
• 239000008107 starch Substances 0.000 description 5
• 229940124549 vasodilator Drugs 0.000 description 5
• 239000003071 vasodilator agent Substances 0.000 description 5
• KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 4
• BDNLOHSMZUXJNE-UHFFFAOYSA-N 2-(2-pyrimidin-2-yloxyethyl)-6-(4-trimethylsilylphenyl)-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC([Si](C)(C)C)=CC=C1C1=CN2C(=O)N(CCOC=3N=CC=CN=3)N=C2C=C1 BDNLOHSMZUXJNE-UHFFFAOYSA-N 0.000 description 4
• YFLRCGNFZGDKJZ-KRWDZBQOSA-N 2-[(2s)-3-methoxy-2-[3-(trifluoromethyl)pyridin-2-yl]oxypropyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C([C@@H](COC)OC=1C(=CC=CN=1)C(F)(F)F)N(C(N1C=2)=O)N=C1C=CC=2C1=CC=C(OC(F)(F)F)C=C1 YFLRCGNFZGDKJZ-KRWDZBQOSA-N 0.000 description 4
• FVJXVFFYXMUTMD-UHFFFAOYSA-N 2-[(3-methyl-1,2,4-oxadiazol-5-yl)methyl]-6-[4-(trifluoromethyl)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CC1=NOC(CN2C(N3C=C(C=CC3=N2)C=2C=CC(=CC=2)C(F)(F)F)=O)=N1 FVJXVFFYXMUTMD-UHFFFAOYSA-N 0.000 description 4
• WSQMBQWQWAJCSH-UHFFFAOYSA-N 2-[(4-cyclopropyl-1,3-oxazol-2-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CC=3OC=C(N=3)C3CC3)N=C2C=C1 WSQMBQWQWAJCSH-UHFFFAOYSA-N 0.000 description 4
• ZOVVXDVDXFAXEL-UHFFFAOYSA-N 2-[(5-cyclopropyl-1,3,4-oxadiazol-2-yl)methyl]-6-[4-(4-fluorophenoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(F)=CC=C1OC1=CC=C(C2=CN3C(=O)N(CC=4OC(=NN=4)C4CC4)N=C3C=C2)C=C1 ZOVVXDVDXFAXEL-UHFFFAOYSA-N 0.000 description 4
• FLWDCZOHCTZLJQ-UHFFFAOYSA-N 2-[(5-cyclopropyl-1,3,4-thiadiazol-2-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CC=3SC(=NN=3)C3CC3)N=C2C=C1 FLWDCZOHCTZLJQ-UHFFFAOYSA-N 0.000 description 4
• CPZBZRZORXDGGZ-UHFFFAOYSA-N 2-[(5-methyl-1,2,4-oxadiazol-3-yl)methyl]-6-[4-(trifluoromethyl)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound O1C(C)=NC(CN2C(N3C=C(C=CC3=N2)C=2C=CC(=CC=2)C(F)(F)F)=O)=N1 CPZBZRZORXDGGZ-UHFFFAOYSA-N 0.000 description 4
• LROYJVODHXKYIJ-UHFFFAOYSA-N 2-[2-(2-chlorophenoxy)ethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCOC=3C(=CC=CC=3)Cl)N=C2C=C1 LROYJVODHXKYIJ-UHFFFAOYSA-N 0.000 description 4
• WNCIIWSWCMIMQU-UHFFFAOYSA-N 2-[2-(4-methylphenoxy)ethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(C)=CC=C1OCCN1C(=O)N2C=C(C=3C=CC(OC(F)(F)F)=CC=3)C=CC2=N1 WNCIIWSWCMIMQU-UHFFFAOYSA-N 0.000 description 4
• GUKRGCNHZGAJRU-UHFFFAOYSA-N 2-[2-(5-methoxypyrimidin-2-yl)oxyethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound N1=CC(OC)=CN=C1OCCN1C(=O)N2C=C(C=3C=CC(OC(F)(F)F)=CC=3)C=CC2=N1 GUKRGCNHZGAJRU-UHFFFAOYSA-N 0.000 description 4
• DCAIURRVFNJFSR-UHFFFAOYSA-N 2-[2-[4-(2-hydroxyethoxy)pyrimidin-2-yl]oxyethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound OCCOC1=CC=NC(OCCN2C(N3C=C(C=CC3=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=N1 DCAIURRVFNJFSR-UHFFFAOYSA-N 0.000 description 4
• DXJAQZHODOOFHY-UHFFFAOYSA-N 2-[[3-(methoxymethyl)-1,2,4-oxadiazol-5-yl]methyl]-6-[4-(trifluoromethyl)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound COCC1=NOC(CN2C(N3C=C(C=CC3=N2)C=2C=CC(=CC=2)C(F)(F)F)=O)=N1 DXJAQZHODOOFHY-UHFFFAOYSA-N 0.000 description 4
• CIUYUJJQZDDGTM-FIBGUPNXSA-N 2-[[3-(trideuteriomethyl)-1,2,4-oxadiazol-5-yl]methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound [2H]C([2H])([2H])C1=NOC(CN2C(N3C=C(C=CC3=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=N1 CIUYUJJQZDDGTM-FIBGUPNXSA-N 0.000 description 4
• ARDUIERVYQWNFN-UHFFFAOYSA-N 2-[[5-(3-methylpyridin-2-yl)-1,2-oxazol-3-yl]methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CC1=CC=CN=C1C1=CC(CN2C(N3C=C(C=CC3=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=NO1 ARDUIERVYQWNFN-UHFFFAOYSA-N 0.000 description 4
• QVMKWIQYYVXBPJ-UHFFFAOYSA-N 2-[[5-(chloromethyl)-1,2,4-oxadiazol-3-yl]methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CC=3N=C(CCl)ON=3)N=C2C=C1 QVMKWIQYYVXBPJ-UHFFFAOYSA-N 0.000 description 4
• MYLLQEZLGWNREX-UHFFFAOYSA-N 2-[[5-(difluoromethyl)-1,2,4-oxadiazol-3-yl]methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound O1C(C(F)F)=NC(CN2C(N3C=C(C=CC3=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=N1 MYLLQEZLGWNREX-UHFFFAOYSA-N 0.000 description 4
• MJKBHISAVSPHNM-UHFFFAOYSA-N 2-[[5-[(2-ethoxyphenoxy)methyl]-1,2,4-oxadiazol-3-yl]methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CCOC1=CC=CC=C1OCC1=NC(CN2C(N3C=C(C=CC3=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=NO1 MJKBHISAVSPHNM-UHFFFAOYSA-N 0.000 description 4
• XHQYGWNZSTUTKL-UHFFFAOYSA-N 6-(3,5-difluoro-4-phenoxyphenyl)-2-[(3-methyl-1,2,4-oxadiazol-5-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CC1=NOC(CN2C(N3C=C(C=CC3=N2)C=2C=C(F)C(OC=3C=CC=CC=3)=C(F)C=2)=O)=N1 XHQYGWNZSTUTKL-UHFFFAOYSA-N 0.000 description 4
• CYVQWKYIMKBUQR-UHFFFAOYSA-N 6-[4-(4-fluorophenoxy)phenyl]-2-[(3-methyl-1,2,4-oxadiazol-5-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CC1=NOC(CN2C(N3C=C(C=CC3=N2)C=2C=CC(OC=3C=CC(F)=CC=3)=CC=2)=O)=N1 CYVQWKYIMKBUQR-UHFFFAOYSA-N 0.000 description 4
• DTAYFBAOZRTZFV-UHFFFAOYSA-N 6-[4-(4-fluorophenoxy)phenyl]-2-[[5-(hydroxymethyl)-1,2,4-oxadiazol-3-yl]methyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound O1C(CO)=NC(CN2C(N3C=C(C=CC3=N2)C=2C=CC(OC=3C=CC(F)=CC=3)=CC=2)=O)=N1 DTAYFBAOZRTZFV-UHFFFAOYSA-N 0.000 description 4
• KHJJLXOPUJOWGC-UHFFFAOYSA-N 6-[4-(trifluoromethoxy)phenyl]-2-[2-[5-(trifluoromethyl)pyrimidin-2-yl]oxyethyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCOC=3N=CC(=CN=3)C(F)(F)F)N=C2C=C1 KHJJLXOPUJOWGC-UHFFFAOYSA-N 0.000 description 4
• GPVLBTKDPJWJQG-UHFFFAOYSA-N 6-[4-(trifluoromethoxy)phenyl]-2-[3-[2-(trifluoromethyl)phenoxy]propyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCCOC=3C(=CC=CC=3)C(F)(F)F)N=C2C=C1 GPVLBTKDPJWJQG-UHFFFAOYSA-N 0.000 description 4
• KZVFUYHFHBBPPD-UHFFFAOYSA-N 6-bromo-2h-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=C(Br)C=CC2=NNC(=O)N21 KZVFUYHFHBBPPD-UHFFFAOYSA-N 0.000 description 4
• 239000005541 ACE inhibitor Substances 0.000 description 4
• ZKHQWZAMYRWXGA-KQYNXXCUSA-N Adenosine triphosphate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O ZKHQWZAMYRWXGA-KQYNXXCUSA-N 0.000 description 4
• ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-UHFFFAOYSA-N 0.000 description 4
• 241000699802 Cricetulus griseus Species 0.000 description 4
• BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
• 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 4
• 201000001068 Prinzmetal angina Diseases 0.000 description 4
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
• 206010063837 Reperfusion injury Diseases 0.000 description 4
• UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 4
• 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 description 4
• 206010003119 arrhythmia Diseases 0.000 description 4
• 239000012298 atmosphere Substances 0.000 description 4
• 239000011203 carbon fibre reinforced carbon Substances 0.000 description 4
• 229940097217 cardiac glycoside Drugs 0.000 description 4
• 239000002368 cardiac glycoside Substances 0.000 description 4
• 238000004587 chromatography analysis Methods 0.000 description 4
• 239000012230 colorless oil Substances 0.000 description 4
• 239000002299 complementary DNA Substances 0.000 description 4
• 239000008121 dextrose Substances 0.000 description 4
• 238000010790 dilution Methods 0.000 description 4
• 239000012895 dilution Substances 0.000 description 4
• 239000002934 diuretic Substances 0.000 description 4
• 229940030606 diuretics Drugs 0.000 description 4
• 239000002552 dosage form Substances 0.000 description 4
• 238000005516 engineering process Methods 0.000 description 4
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
• 239000000706 filtrate Substances 0.000 description 4
• 150000002430 hydrocarbons Chemical group 0.000 description 4
• 239000003112 inhibitor Substances 0.000 description 4
• 230000002401 inhibitory effect Effects 0.000 description 4
• 230000005764 inhibitory process Effects 0.000 description 4
• 238000002347 injection Methods 0.000 description 4
• 239000007924 injection Substances 0.000 description 4
• 238000005259 measurement Methods 0.000 description 4
• 230000002503 metabolic effect Effects 0.000 description 4
• VWPOSFSPZNDTMJ-UCWKZMIHSA-N nadolol Chemical compound C1[C@@H](O)[C@@H](O)CC2=C1C=CC=C2OCC(O)CNC(C)(C)C VWPOSFSPZNDTMJ-UCWKZMIHSA-N 0.000 description 4
• 150000002823 nitrates Chemical class 0.000 description 4
• 239000003960 organic solvent Substances 0.000 description 4
• 210000001672 ovary Anatomy 0.000 description 4
• XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 4
• 239000006187 pill Substances 0.000 description 4
• 229920000642 polymer Polymers 0.000 description 4
• 229920006395 saturated elastomer Polymers 0.000 description 4
• BLFQGGGGFNSJKA-XHXSRVRCSA-N sertraline hydrochloride Chemical compound Cl.C1([C@@H]2CC[C@@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 BLFQGGGGFNSJKA-XHXSRVRCSA-N 0.000 description 4
• 239000000377 silicon dioxide Substances 0.000 description 4
• 229930002534 steroid glycoside Natural products 0.000 description 4
• 150000008143 steroidal glycosides Chemical class 0.000 description 4
• 125000005346 substituted cycloalkyl group Chemical group 0.000 description 4
• 239000000454 talc Substances 0.000 description 4
• 235000012222 talc Nutrition 0.000 description 4
• 229910052623 talc Inorganic materials 0.000 description 4
• 230000036962 time dependent Effects 0.000 description 4
• 239000003981 vehicle Substances 0.000 description 4
• 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 3
• JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 3
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 3
• WKDQCKNSCDAWPO-UHFFFAOYSA-N 2-(2-morpholin-4-ylethyl)-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCN3CCOCC3)N=C2C=C1 WKDQCKNSCDAWPO-UHFFFAOYSA-N 0.000 description 3
• MHNUAGFSAJGFAI-UHFFFAOYSA-N 2-(pyrimidin-2-ylmethyl)-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CC=3N=CC=CN=3)N=C2C=C1 MHNUAGFSAJGFAI-UHFFFAOYSA-N 0.000 description 3
• HUUNVXZDGAPENJ-UHFFFAOYSA-N 2-(quinolin-8-ylmethyl)-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CC=3C4=NC=CC=C4C=CC=3)N=C2C=C1 HUUNVXZDGAPENJ-UHFFFAOYSA-N 0.000 description 3
• HVBIGQNMFRGYHK-UHFFFAOYSA-N 2-[(3-ethyl-1,2,4-oxadiazol-5-yl)methyl]-6-[4-(trifluoromethyl)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CCC1=NOC(CN2C(N3C=C(C=CC3=N2)C=2C=CC(=CC=2)C(F)(F)F)=O)=N1 HVBIGQNMFRGYHK-UHFFFAOYSA-N 0.000 description 3
• CIUYUJJQZDDGTM-UHFFFAOYSA-N 2-[(3-methyl-1,2,4-oxadiazol-5-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CC1=NOC(CN2C(N3C=C(C=CC3=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=N1 CIUYUJJQZDDGTM-UHFFFAOYSA-N 0.000 description 3
• HIXXOGSPULBPEX-UHFFFAOYSA-N 2-[(4,5-dimethyl-1,3-oxazol-2-yl)methyl]-6-[4-(trifluoromethyl)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound O1C(C)=C(C)N=C1CN1C(=O)N2C=C(C=3C=CC(=CC=3)C(F)(F)F)C=CC2=N1 HIXXOGSPULBPEX-UHFFFAOYSA-N 0.000 description 3
• PYEUJAYDBPQGGK-UHFFFAOYSA-N 2-[2-(4,6-dimethylpyrimidin-2-yl)oxyethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CC1=CC(C)=NC(OCCN2C(N3C=C(C=CC3=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=N1 PYEUJAYDBPQGGK-UHFFFAOYSA-N 0.000 description 3
• GCNDSKRXUCBSLW-UHFFFAOYSA-N 2-[2-(4-methylpyridin-2-yl)ethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CC1=CC=NC(CCN2C(N3C=C(C=CC3=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=C1 GCNDSKRXUCBSLW-UHFFFAOYSA-N 0.000 description 3
• IDVVEYCFEYNEGJ-UHFFFAOYSA-N 2-[2-[4-(dimethylamino)-5-fluoropyrimidin-2-yl]oxyethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=C(F)C(N(C)C)=NC(OCCN2C(N3C=C(C=CC3=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=N1 IDVVEYCFEYNEGJ-UHFFFAOYSA-N 0.000 description 3
• RQALVPINBQGMCE-UHFFFAOYSA-N 2-[2-ethoxy-3-(4-fluoro-2-methoxyphenoxy)propyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound N1=C2C=CC(C=3C=CC(OC(F)(F)F)=CC=3)=CN2C(=O)N1CC(OCC)COC1=CC=C(F)C=C1OC RQALVPINBQGMCE-UHFFFAOYSA-N 0.000 description 3
• ACSLOAIBGIAKBZ-UHFFFAOYSA-N 2-[2-ethoxy-3-[(2-methyl-1,3-benzothiazol-6-yl)oxy]propyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C=1C=C2N=C(C)SC2=CC=1OCC(OCC)CN(C(N1C=2)=O)N=C1C=CC=2C1=CC=C(OC(F)(F)F)C=C1 ACSLOAIBGIAKBZ-UHFFFAOYSA-N 0.000 description 3
• KWNBHJZWBRZVEO-UHFFFAOYSA-N 2-[2-hydroxy-3-[(2-methyl-1,3-benzothiazol-6-yl)oxy]propyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=C2SC(C)=NC2=CC=C1OCC(O)CN(C(N1C=2)=O)N=C1C=CC=2C1=CC=C(OC(F)(F)F)C=C1 KWNBHJZWBRZVEO-UHFFFAOYSA-N 0.000 description 3
• QRXWNGQHWYMZFJ-UHFFFAOYSA-N 2-[2-hydroxy-3-[3-oxo-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-2-yl]propoxy]benzonitrile Chemical compound N1=C2C=CC(C=3C=CC(OC(F)(F)F)=CC=3)=CN2C(=O)N1CC(O)COC1=CC=CC=C1C#N QRXWNGQHWYMZFJ-UHFFFAOYSA-N 0.000 description 3
• VLGOKQMHVAJDGL-UHFFFAOYSA-N 2-[[3-(methoxymethyl)-1,2,4-oxadiazol-5-yl]methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound COCC1=NOC(CN2C(N3C=C(C=CC3=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=N1 VLGOKQMHVAJDGL-UHFFFAOYSA-N 0.000 description 3
• MNDYBFMGLXVTSQ-HNNXBMFYSA-N 2-[[5-[(4s)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,2,4-oxadiazol-3-yl]methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound O1C(C)(C)OC[C@H]1C1=NC(CN2C(N3C=C(C=CC3=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=NO1 MNDYBFMGLXVTSQ-HNNXBMFYSA-N 0.000 description 3
• BHJJYZZAPARKEZ-UHFFFAOYSA-N 5-methyl-6-[4-(trifluoromethoxy)phenyl]-2h-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC2=NNC(=O)N2C(C)=C1C1=CC=C(OC(F)(F)F)C=C1 BHJJYZZAPARKEZ-UHFFFAOYSA-N 0.000 description 3
• UMBHAMWTALDITM-UHFFFAOYSA-N 6-(3,4-dichlorophenyl)-2-[(3-methyl-1,2,4-oxadiazol-5-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CC1=NOC(CN2C(N3C=C(C=CC3=N2)C=2C=C(Cl)C(Cl)=CC=2)=O)=N1 UMBHAMWTALDITM-UHFFFAOYSA-N 0.000 description 3
• LWCNUTAQWBMTMY-UHFFFAOYSA-N 6-(4-chloro-3-fluorophenyl)-2-[(3-methyl-1,2,4-oxadiazol-5-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CC1=NOC(CN2C(N3C=C(C=CC3=N2)C=2C=C(F)C(Cl)=CC=2)=O)=N1 LWCNUTAQWBMTMY-UHFFFAOYSA-N 0.000 description 3
• RPWUFPVCLXWYCF-UHFFFAOYSA-N 6-(4-chlorophenyl)-2-[(3-methyl-1,2,4-oxadiazol-5-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CC1=NOC(CN2C(N3C=C(C=CC3=N2)C=2C=CC(Cl)=CC=2)=O)=N1 RPWUFPVCLXWYCF-UHFFFAOYSA-N 0.000 description 3
• FJMLVEMQSDYXRP-UHFFFAOYSA-N 6-[3-fluoro-4-(trifluoromethoxy)phenyl]-2-[(3-methyl-1,2,4-oxadiazol-5-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CC1=NOC(CN2C(N3C=C(C=CC3=N2)C=2C=C(F)C(OC(F)(F)F)=CC=2)=O)=N1 FJMLVEMQSDYXRP-UHFFFAOYSA-N 0.000 description 3
• FVCUQQGWODVVEB-UHFFFAOYSA-N 6-[4-(4-chlorophenoxy)phenyl]-2-(2-pyrimidin-2-yloxyethyl)-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(Cl)=CC=C1OC1=CC=C(C2=CN3C(=O)N(CCOC=4N=CC=CN=4)N=C3C=C2)C=C1 FVCUQQGWODVVEB-UHFFFAOYSA-N 0.000 description 3
• FVWAVLHWMKAFBA-UHFFFAOYSA-N 6-[4-(4-fluorophenoxy)phenyl]-2-[(5-methyl-1,2,4-oxadiazol-3-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound O1C(C)=NC(CN2C(N3C=C(C=CC3=N2)C=2C=CC(OC=3C=CC(F)=CC=3)=CC=2)=O)=N1 FVWAVLHWMKAFBA-UHFFFAOYSA-N 0.000 description 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
• XPCFTKFZXHTYIP-PMACEKPBSA-N Benazepril Chemical compound C([C@@H](C(=O)OCC)N[C@@H]1C(N(CC(O)=O)C2=CC=CC=C2CC1)=O)CC1=CC=CC=C1 XPCFTKFZXHTYIP-PMACEKPBSA-N 0.000 description 3
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
• 102000003922 Calcium Channels Human genes 0.000 description 3
• 108090000312 Calcium Channels Proteins 0.000 description 3
• 229940127291 Calcium channel antagonist Drugs 0.000 description 3
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
• JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 3
• FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 3
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
• KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 3
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
• 239000012981 Hank's balanced salt solution Substances 0.000 description 3
• 101000684826 Homo sapiens Sodium channel protein type 2 subunit alpha Proteins 0.000 description 3
• 206010020772 Hypertension Diseases 0.000 description 3
• 108020004684 Internal Ribosome Entry Sites Proteins 0.000 description 3
• 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 3
• OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical class OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
• 229930195725 Mannitol Natural products 0.000 description 3
• 241001465754 Metazoa Species 0.000 description 3
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
• 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 3
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical class OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
• 229910019213 POCl3 Inorganic materials 0.000 description 3
• 208000018262 Peripheral vascular disease Diseases 0.000 description 3
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
• 102100023150 Sodium channel protein type 2 subunit alpha Human genes 0.000 description 3
• 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 3
• 229930006000 Sucrose Natural products 0.000 description 3
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
• 238000006069 Suzuki reaction reaction Methods 0.000 description 3
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
• HUOFUOCSQCYFPW-UHFFFAOYSA-N [4-(trifluoromethoxy)phenyl]boronic acid Chemical compound OB(O)C1=CC=C(OC(F)(F)F)C=C1 HUOFUOCSQCYFPW-UHFFFAOYSA-N 0.000 description 3
• 239000012190 activator Substances 0.000 description 3
• 150000001350 alkyl halides Chemical class 0.000 description 3
• 238000000540 analysis of variance Methods 0.000 description 3
• 230000003257 anti-anginal effect Effects 0.000 description 3
• 229940124345 antianginal agent Drugs 0.000 description 3
• 229940127219 anticoagulant drug Drugs 0.000 description 3
• 229960004676 antithrombotic agent Drugs 0.000 description 3
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
• 210000004369 blood Anatomy 0.000 description 3
• 239000008280 blood Substances 0.000 description 3
• 150000001642 boronic acid derivatives Chemical class 0.000 description 3
• 125000005620 boronic acid group Chemical class 0.000 description 3
• SNPPWIUOZRMYNY-UHFFFAOYSA-N bupropion Chemical compound CC(C)(C)NC(C)C(=O)C1=CC=CC(Cl)=C1 SNPPWIUOZRMYNY-UHFFFAOYSA-N 0.000 description 3
• 239000011575 calcium Substances 0.000 description 3
• 229910052791 calcium Inorganic materials 0.000 description 3
• 239000000480 calcium channel blocker Substances 0.000 description 3
• 229910052799 carbon Inorganic materials 0.000 description 3
• 210000000748 cardiovascular system Anatomy 0.000 description 3
• 239000003054 catalyst Substances 0.000 description 3
• 239000000460 chlorine Substances 0.000 description 3
• HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 3
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
• 230000035602 clotting Effects 0.000 description 3
• 238000000576 coating method Methods 0.000 description 3
• 229910052681 coesite Inorganic materials 0.000 description 3
• 229910052906 cristobalite Inorganic materials 0.000 description 3
• 125000006165 cyclic alkyl group Chemical group 0.000 description 3
• WLVKDFJTYKELLQ-UHFFFAOYSA-N cyclopropylboronic acid Chemical compound OB(O)C1CC1 WLVKDFJTYKELLQ-UHFFFAOYSA-N 0.000 description 3
• 229960004042 diazoxide Drugs 0.000 description 3
• 239000003085 diluting agent Substances 0.000 description 3
• IZEKFCXSFNUWAM-UHFFFAOYSA-N dipyridamole Chemical compound C=12N=C(N(CCO)CCO)N=C(N3CCCCC3)C2=NC(N(CCO)CCO)=NC=1N1CCCCC1 IZEKFCXSFNUWAM-UHFFFAOYSA-N 0.000 description 3
• 229960002768 dipyridamole Drugs 0.000 description 3
• 239000006185 dispersion Substances 0.000 description 3
• 238000004090 dissolution Methods 0.000 description 3
• ZQTNQVWKHCQYLQ-UHFFFAOYSA-N dronedarone Chemical compound C1=CC(OCCCN(CCCC)CCCC)=CC=C1C(=O)C1=C(CCCC)OC2=CC=C(NS(C)(=O)=O)C=C12 ZQTNQVWKHCQYLQ-UHFFFAOYSA-N 0.000 description 3
• 229960002084 dronedarone Drugs 0.000 description 3
• 239000003937 drug carrier Substances 0.000 description 3
• 239000003527 fibrinolytic agent Substances 0.000 description 3
• 125000000524 functional group Chemical group 0.000 description 3
• 239000007903 gelatin capsule Substances 0.000 description 3
• 239000008187 granular material Substances 0.000 description 3
• 125000005842 heteroatom Chemical group 0.000 description 3
• 239000012442 inert solvent Substances 0.000 description 3
• 238000001802 infusion Methods 0.000 description 3
• 238000007689 inspection Methods 0.000 description 3
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
• 239000008101 lactose Substances 0.000 description 3
• 239000010410 layer Substances 0.000 description 3
• 239000003446 ligand Substances 0.000 description 3
• PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 description 3
• 239000000594 mannitol Substances 0.000 description 3
• 235000010355 mannitol Nutrition 0.000 description 3
• 229910052751 metal Inorganic materials 0.000 description 3
• 239000002184 metal Substances 0.000 description 3
• 229960001597 nifedipine Drugs 0.000 description 3
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
• 238000012856 packing Methods 0.000 description 3
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
• 239000000106 platelet aggregation inhibitor Substances 0.000 description 3
• 239000001267 polyvinylpyrrolidone Substances 0.000 description 3
• 229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
• 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
• IENZQIKPVFGBNW-UHFFFAOYSA-N prazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 IENZQIKPVFGBNW-UHFFFAOYSA-N 0.000 description 3
• 229960001289 prazosin Drugs 0.000 description 3
• WFXFYZULCQKPIP-UHFFFAOYSA-N prazosin hydrochloride Chemical compound [H+].[Cl-].N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 WFXFYZULCQKPIP-UHFFFAOYSA-N 0.000 description 3
• 238000002953 preparative HPLC Methods 0.000 description 3
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
• ZIEWSZYVEDTXGH-UHFFFAOYSA-N pyrimidine-4-carbonitrile Chemical compound N#CC1=CC=NC=N1 ZIEWSZYVEDTXGH-UHFFFAOYSA-N 0.000 description 3
• 229940099099 ranexa Drugs 0.000 description 3
• 230000003252 repetitive effect Effects 0.000 description 3
• 235000012239 silicon dioxide Nutrition 0.000 description 3
• 229940125794 sodium channel blocker Drugs 0.000 description 3
• 239000011775 sodium fluoride Substances 0.000 description 3
• 235000013024 sodium fluoride Nutrition 0.000 description 3
• 229910000104 sodium hydride Inorganic materials 0.000 description 3
• 229910052682 stishovite Inorganic materials 0.000 description 3
• 125000005017 substituted alkenyl group Chemical group 0.000 description 3
• 239000005720 sucrose Substances 0.000 description 3
• 229910052717 sulfur Inorganic materials 0.000 description 3
• 239000011593 sulfur Substances 0.000 description 3
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
• 229960000103 thrombolytic agent Drugs 0.000 description 3
• FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 description 3
• 229910052905 tridymite Inorganic materials 0.000 description 3
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 3
• 206010047302 ventricular tachycardia Diseases 0.000 description 3
• 229960001722 verapamil Drugs 0.000 description 3
• XWTYSIMOBUGWOL-UHFFFAOYSA-N (+-)-Terbutaline Chemical compound CC(C)(C)NCC(O)C1=CC(O)=CC(O)=C1 XWTYSIMOBUGWOL-UHFFFAOYSA-N 0.000 description 2
• SCJYBEPFUOGAME-PPHPATTJSA-N (2s)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid;6-chloro-1,1-dioxo-4h-1$l^{6},2,4-benzothiadiazine-7-sulfonamide Chemical compound OC(=O)[C@](N)(C)CC1=CC=C(O)C(O)=C1.C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NC=NS2(=O)=O SCJYBEPFUOGAME-PPHPATTJSA-N 0.000 description 2
• BIDNLKIUORFRQP-XYGFDPSESA-N (2s,4s)-4-cyclohexyl-1-[2-[[(1s)-2-methyl-1-propanoyloxypropoxy]-(4-phenylbutyl)phosphoryl]acetyl]pyrrolidine-2-carboxylic acid Chemical compound C([P@@](=O)(O[C@H](OC(=O)CC)C(C)C)CC(=O)N1[C@@H](C[C@H](C1)C1CCCCC1)C(O)=O)CCCC1=CC=CC=C1 BIDNLKIUORFRQP-XYGFDPSESA-N 0.000 description 2
• ZGGHKIMDNBDHJB-NRFPMOEYSA-M (3R,5S)-fluvastatin sodium Chemical compound [Na+].C12=CC=CC=C2N(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 ZGGHKIMDNBDHJB-NRFPMOEYSA-M 0.000 description 2
• QYQLEYTXFMOLEI-UHFFFAOYSA-N (5-bromopyridin-2-yl)hydrazine Chemical compound NNC1=CC=C(Br)C=N1 QYQLEYTXFMOLEI-UHFFFAOYSA-N 0.000 description 2
• WDLWHQDACQUCJR-ZAMMOSSLSA-N (6r,7r)-7-[[(2r)-2-azaniumyl-2-(4-hydroxyphenyl)acetyl]amino]-8-oxo-3-[(e)-prop-1-enyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)/C=C/C)C(O)=O)=CC=C(O)C=C1 WDLWHQDACQUCJR-ZAMMOSSLSA-N 0.000 description 2
• TWBNMYSKRDRHAT-RCWTXCDDSA-N (S)-timolol hemihydrate Chemical compound O.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1 TWBNMYSKRDRHAT-RCWTXCDDSA-N 0.000 description 2
• WLRMANUAADYWEA-NWASOUNVSA-N (S)-timolol maleate Chemical compound OC(=O)\C=C/C(O)=O.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1 WLRMANUAADYWEA-NWASOUNVSA-N 0.000 description 2
• WSTAITCRSVOCTK-UHFFFAOYSA-N 1,4-diazabicyclo[2.2.2]octane;trimethylalumane Chemical compound C[Al](C)C.C[Al](C)C.C1CN2CCN1CC2 WSTAITCRSVOCTK-UHFFFAOYSA-N 0.000 description 2
• UUUHXMGGBIUAPW-UHFFFAOYSA-N 1-[1-[2-[[5-amino-2-[[1-[5-(diaminomethylideneamino)-2-[[1-[3-(1h-indol-3-yl)-2-[(5-oxopyrrolidine-2-carbonyl)amino]propanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbon Chemical compound C1CCC(C(=O)N2C(CCC2)C(O)=O)N1C(=O)C(C(C)CC)NC(=O)C(CCC(N)=O)NC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C1CCCN1C(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCC(=O)N1 UUUHXMGGBIUAPW-UHFFFAOYSA-N 0.000 description 2
• UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 2
• NLCZQIFBCSBGFC-UHFFFAOYSA-N 2-(2-bromoethyl)-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCBr)N=C2C=C1 NLCZQIFBCSBGFC-UHFFFAOYSA-N 0.000 description 2
• OBTZDIRUQWFRFZ-UHFFFAOYSA-N 2-(5-methylfuran-2-yl)-n-(4-methylphenyl)quinoline-4-carboxamide Chemical compound O1C(C)=CC=C1C1=CC(C(=O)NC=2C=CC(C)=CC=2)=C(C=CC=C2)C2=N1 OBTZDIRUQWFRFZ-UHFFFAOYSA-N 0.000 description 2
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
• AVSQLPAJCOPVGM-UHFFFAOYSA-N 2-[(1-methylpyrazol-4-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=NN(C)C=C1CN1C(=O)N2C=C(C=3C=CC(OC(F)(F)F)=CC=3)C=CC2=N1 AVSQLPAJCOPVGM-UHFFFAOYSA-N 0.000 description 2
• YWPYCDLKADHMCQ-SFHVURJKSA-N 2-[(2s)-3-(2-chlorophenoxy)-2-methoxypropyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C([C@@H](OC)CN1C(N2C=C(C=CC2=N1)C=1C=CC(OC(F)(F)F)=CC=1)=O)OC1=CC=CC=C1Cl YWPYCDLKADHMCQ-SFHVURJKSA-N 0.000 description 2
• NGXPLUHGOPEZPQ-UHFFFAOYSA-N 2-[(3-methyl-1,2,4-oxadiazol-5-yl)methyl]-6-(4-trimethylsilylphenyl)-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CC1=NOC(CN2C(N3C=C(C=CC3=N2)C=2C=CC(=CC=2)[Si](C)(C)C)=O)=N1 NGXPLUHGOPEZPQ-UHFFFAOYSA-N 0.000 description 2
• DCUSGGLEJVNADI-UHFFFAOYSA-N 2-[(3-methyl-1,2,4-oxadiazol-5-yl)methyl]-6-[2-methyl-4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CC1=NOC(CN2C(N3C=C(C=CC3=N2)C=2C(=CC(OC(F)(F)F)=CC=2)C)=O)=N1 DCUSGGLEJVNADI-UHFFFAOYSA-N 0.000 description 2
• PYCKDNAEOSDPSW-UHFFFAOYSA-N 2-[(3-methyl-1,2,4-oxadiazol-5-yl)methyl]-6-[4-(2,2,2-trifluoroethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CC1=NOC(CN2C(N3C=C(C=CC3=N2)C=2C=CC(OCC(F)(F)F)=CC=2)=O)=N1 PYCKDNAEOSDPSW-UHFFFAOYSA-N 0.000 description 2
• GKAJUYNXBRLXRT-UHFFFAOYSA-N 2-[(4,5-dichloro-2-methoxyphenoxy)methyl]oxirane Chemical compound COC1=CC(Cl)=C(Cl)C=C1OCC1OC1 GKAJUYNXBRLXRT-UHFFFAOYSA-N 0.000 description 2
• LVIVCBYJGVUQAJ-UHFFFAOYSA-N 2-[(4-methyl-1,2,5-oxadiazol-3-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CC1=NON=C1CN1C(=O)N2C=C(C=3C=CC(OC(F)(F)F)=CC=3)C=CC2=N1 LVIVCBYJGVUQAJ-UHFFFAOYSA-N 0.000 description 2
• BSUJKFRZIQGHKG-UHFFFAOYSA-N 2-[(4-phenyl-1,2,5-oxadiazol-3-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CC=3C(=NON=3)C=3C=CC=CC=3)N=C2C=C1 BSUJKFRZIQGHKG-UHFFFAOYSA-N 0.000 description 2
• CRLVACGUSHLQEQ-UHFFFAOYSA-N 2-[(5-cyclopropyl-1,2,4-oxadiazol-3-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CC=3N=C(ON=3)C3CC3)N=C2C=C1 CRLVACGUSHLQEQ-UHFFFAOYSA-N 0.000 description 2
• RRAJQAYXEXKFHG-UHFFFAOYSA-N 2-[(5-cyclopropyl-2-methylpyrazol-3-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CN1N=C(C2CC2)C=C1CN(C(N1C=2)=O)N=C1C=CC=2C1=CC=C(OC(F)(F)F)C=C1 RRAJQAYXEXKFHG-UHFFFAOYSA-N 0.000 description 2
• MGKQMRGQRNCSMN-UHFFFAOYSA-N 2-[(5-methyl-1,2,4-oxadiazol-3-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound O1C(C)=NC(CN2C(N3C=C(C=CC3=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=N1 MGKQMRGQRNCSMN-UHFFFAOYSA-N 0.000 description 2
• OYTKMZYFUNPNRK-UHFFFAOYSA-N 2-[(5-methyl-1,3,4-oxadiazol-2-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound O1C(C)=NN=C1CN1C(=O)N2C=C(C=3C=CC(OC(F)(F)F)=CC=3)C=CC2=N1 OYTKMZYFUNPNRK-UHFFFAOYSA-N 0.000 description 2
• JMCLXORBNBWOEO-UHFFFAOYSA-N 2-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CN(C(N1C=2)=O)N=C1C=CC=2C1=CC=C(OC(F)(F)F)C=C1 JMCLXORBNBWOEO-UHFFFAOYSA-N 0.000 description 2
• GCWWAYFSWSKCCY-UHFFFAOYSA-N 2-[(5-pyridin-2-yl-1,2-oxazol-3-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CC3=NOC(=C3)C=3N=CC=CC=3)N=C2C=C1 GCWWAYFSWSKCCY-UHFFFAOYSA-N 0.000 description 2
• HCGFFJNOBZZEFK-UHFFFAOYSA-N 2-[3-(4-chloropyridin-3-yl)prop-2-ynyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CC#CC=3C(=CC=NC=3)Cl)N=C2C=C1 HCGFFJNOBZZEFK-UHFFFAOYSA-N 0.000 description 2
• IISQOFPCGIIYLN-UHFFFAOYSA-N 2-[[3-(2-chlorophenyl)-1,2,4-oxadiazol-5-yl]methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CC=3ON=C(N=3)C=3C(=CC=CC=3)Cl)N=C2C=C1 IISQOFPCGIIYLN-UHFFFAOYSA-N 0.000 description 2
• FMKGJQHNYMWDFJ-CVEARBPZSA-N 2-[[4-(2,2-difluoropropoxy)pyrimidin-5-yl]methylamino]-4-[[(1R,4S)-4-hydroxy-3,3-dimethylcyclohexyl]amino]pyrimidine-5-carbonitrile Chemical compound FC(COC1=NC=NC=C1CNC1=NC=C(C(=N1)N[C@H]1CC([C@H](CC1)O)(C)C)C#N)(C)F FMKGJQHNYMWDFJ-CVEARBPZSA-N 0.000 description 2
• QCHBVKBITVXFML-UHFFFAOYSA-N 2-[[5-(2-methoxyphenyl)-1,2,4-oxadiazol-3-yl]methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound COC1=CC=CC=C1C1=NC(CN2C(N3C=C(C=CC3=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=NO1 QCHBVKBITVXFML-UHFFFAOYSA-N 0.000 description 2
• FXEVEXAZTVDNCC-UHFFFAOYSA-N 2-[[5-(methoxymethyl)-1,2,4-oxadiazol-3-yl]methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound O1C(COC)=NC(CN2C(N3C=C(C=CC3=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=N1 FXEVEXAZTVDNCC-UHFFFAOYSA-N 0.000 description 2
• LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 2
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
• VPGAFZYIVIVFPO-UHFFFAOYSA-N 2-triethylsilyloxypropan-1-amine Chemical compound CC[Si](CC)(CC)OC(C)CN VPGAFZYIVIVFPO-UHFFFAOYSA-N 0.000 description 2
• RSPGSHAMFWAJIY-UHFFFAOYSA-N 4-(chloromethyl)-2-cyclopropyl-1,3-oxazole Chemical compound ClCC1=COC(C2CC2)=N1 RSPGSHAMFWAJIY-UHFFFAOYSA-N 0.000 description 2
• FYDQQEVRVKAASZ-UHFFFAOYSA-N 5-(chloromethyl)-3-methyl-1,2,4-oxadiazole Chemical compound CC1=NOC(CCl)=N1 FYDQQEVRVKAASZ-UHFFFAOYSA-N 0.000 description 2
• WWFCNKUCFKPXRI-UHFFFAOYSA-N 6-[4-(4-chlorophenoxy)phenyl]-2-[(3-methyl-1,2,4-oxadiazol-5-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CC1=NOC(CN2C(N3C=C(C=CC3=N2)C=2C=CC(OC=3C=CC(Cl)=CC=3)=CC=2)=O)=N1 WWFCNKUCFKPXRI-UHFFFAOYSA-N 0.000 description 2
• SQZWPCQKGINHDT-UHFFFAOYSA-N 6-[4-(4-chlorophenoxy)phenyl]-2-[(5-methyl-1,2,4-oxadiazol-3-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound O1C(C)=NC(CN2C(N3C=C(C=CC3=N2)C=2C=CC(OC=3C=CC(Cl)=CC=3)=CC=2)=O)=N1 SQZWPCQKGINHDT-UHFFFAOYSA-N 0.000 description 2
• GBFWACWSCPFMSP-UHFFFAOYSA-N 6-[4-(4-fluorophenoxy)phenyl]-2h-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(F)=CC=C1OC1=CC=C(C2=CN3C(=O)NN=C3C=C2)C=C1 GBFWACWSCPFMSP-UHFFFAOYSA-N 0.000 description 2
• ILZUBCPZMJPETC-UHFFFAOYSA-N 6-[4-(trifluoromethoxy)phenyl]-2-[[6-(trifluoromethyl)pyridin-2-yl]methyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CC=3N=C(C=CC=3)C(F)(F)F)N=C2C=C1 ILZUBCPZMJPETC-UHFFFAOYSA-N 0.000 description 2
• VHRSUDSXCMQTMA-PJHHCJLFSA-N 6alpha-methylprednisolone Chemical compound C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)[C@@](O)(C(=O)CO)CC[C@H]21 VHRSUDSXCMQTMA-PJHHCJLFSA-N 0.000 description 2
• KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
• UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
• 101000583076 Anemonia sulcata Delta-actitoxin-Avd1c Proteins 0.000 description 2
• BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 2
• 201000001320 Atherosclerosis Diseases 0.000 description 2
• 206010003658 Atrial Fibrillation Diseases 0.000 description 2
• 239000004255 Butylated hydroxyanisole Substances 0.000 description 2
• JQUCWIWWWKZNCS-LESHARBVSA-N C(C1=CC=CC=C1)(=O)NC=1SC[C@H]2[C@@](N1)(CO[C@H](C2)C)C=2SC=C(N2)NC(=O)C2=NC=C(C=C2)OC(F)F Chemical compound C(C1=CC=CC=C1)(=O)NC=1SC[C@H]2[C@@](N1)(CO[C@H](C2)C)C=2SC=C(N2)NC(=O)C2=NC=C(C=C2)OC(F)F JQUCWIWWWKZNCS-LESHARBVSA-N 0.000 description 2
• 239000002083 C09CA01 - Losartan Substances 0.000 description 2
• JFPVXVDWJQMJEE-QMTHXVAHSA-N Cefuroxime Chemical compound N([C@@H]1C(N2C(=C(COC(N)=O)CS[C@@H]21)C(O)=O)=O)C(=O)C(=NOC)C1=CC=CO1 JFPVXVDWJQMJEE-QMTHXVAHSA-N 0.000 description 2
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
• VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 2
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
• ZNIFSRGNXRYGHF-UHFFFAOYSA-N Clonidine hydrochloride Chemical compound Cl.ClC1=CC=CC(Cl)=C1NC1=NCCN1 ZNIFSRGNXRYGHF-UHFFFAOYSA-N 0.000 description 2
• 238000006646 Dess-Martin oxidation reaction Methods 0.000 description 2
• 108010061435 Enalapril Proteins 0.000 description 2
• 108010066671 Enalaprilat Proteins 0.000 description 2
• ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 2
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
• 108010010803 Gelatin Proteins 0.000 description 2
• AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical class OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
• WDZVGELJXXEGPV-YIXHJXPBSA-N Guanabenz Chemical compound NC(N)=N\N=C\C1=C(Cl)C=CC=C1Cl WDZVGELJXXEGPV-YIXHJXPBSA-N 0.000 description 2
• MCSPBPXATWBACD-GAYQJXMFSA-N Guanabenz acetate Chemical compound CC(O)=O.NC(N)=N\N=C\C1=C(Cl)C=CC=C1Cl MCSPBPXATWBACD-GAYQJXMFSA-N 0.000 description 2
• DGFYECXYGUIODH-UHFFFAOYSA-N Guanfacine hydrochloride Chemical compound Cl.NC(N)=NC(=O)CC1=C(Cl)C=CC=C1Cl DGFYECXYGUIODH-UHFFFAOYSA-N 0.000 description 2
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
• 208000022559 Inflammatory bowel disease Diseases 0.000 description 2
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
• ZFMITUMMTDLWHR-UHFFFAOYSA-N Minoxidil Chemical compound NC1=[N+]([O-])C(N)=CC(N2CCCCC2)=N1 ZFMITUMMTDLWHR-UHFFFAOYSA-N 0.000 description 2
• 238000006751 Mitsunobu reaction Methods 0.000 description 2
• UWWDHYUMIORJTA-HSQYWUDLSA-N Moexipril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2=CC(OC)=C(OC)C=C2C1)C(O)=O)CC1=CC=CC=C1 UWWDHYUMIORJTA-HSQYWUDLSA-N 0.000 description 2
• PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 description 2
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
• HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 2
• QOVYHDHLFPKQQG-NDEPHWFRSA-N N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O Chemical compound N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O QOVYHDHLFPKQQG-NDEPHWFRSA-N 0.000 description 2
• 206010029260 Neuroblastoma Diseases 0.000 description 2
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 2
• 229930182555 Penicillin Natural products 0.000 description 2
• 102000004270 Peptidyl-Dipeptidase A Human genes 0.000 description 2
• 108090000882 Peptidyl-Dipeptidase A Proteins 0.000 description 2
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
• QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical group CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
• 208000003251 Pruritus Diseases 0.000 description 2
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
• LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical class CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
• GIIZNNXWQWCKIB-UHFFFAOYSA-N Serevent Chemical compound C1=C(O)C(CO)=CC(C(O)CNCCCCCCOCCCCC=2C=CC=CC=2)=C1 GIIZNNXWQWCKIB-UHFFFAOYSA-N 0.000 description 2
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
• 208000001871 Tachycardia Diseases 0.000 description 2
• 239000004098 Tetracycline Substances 0.000 description 2
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
• 208000007536 Thrombosis Diseases 0.000 description 2
• 108090000373 Tissue Plasminogen Activator Proteins 0.000 description 2
• 102000003978 Tissue Plasminogen Activator Human genes 0.000 description 2
• 208000018452 Torsade de pointes Diseases 0.000 description 2
• 208000002363 Torsades de Pointes Diseases 0.000 description 2
• VXFJYXUZANRPDJ-WTNASJBWSA-N Trandopril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](C[C@H]2CCCC[C@@H]21)C(O)=O)CC1=CC=CC=C1 VXFJYXUZANRPDJ-WTNASJBWSA-N 0.000 description 2
• 238000010162 Tukey test Methods 0.000 description 2
• 208000009325 Variant Angina Pectoris Diseases 0.000 description 2
• PSLUFJFHTBIXMW-WYEYVKMPSA-N [(3r,4ar,5s,6s,6as,10s,10ar,10bs)-3-ethenyl-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-6-(2-pyridin-2-ylethylcarbamoyloxy)-5,6,6a,8,9,10-hexahydro-2h-benzo[f]chromen-5-yl] acetate Chemical compound O([C@@H]1[C@@H]([C@]2(O[C@](C)(CC(=O)[C@]2(O)[C@@]2(C)[C@@H](O)CCC(C)(C)[C@@H]21)C=C)C)OC(=O)C)C(=O)NCCC1=CC=CC=N1 PSLUFJFHTBIXMW-WYEYVKMPSA-N 0.000 description 2
• SMNRFWMNPDABKZ-WVALLCKVSA-N [[(2R,3S,4R,5S)-5-(2,6-dioxo-3H-pyridin-3-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4S,5R,6R)-4-fluoro-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)C2C=CC(=O)NC2=O)[C@H](O)[C@@H](F)[C@@H]1O SMNRFWMNPDABKZ-WVALLCKVSA-N 0.000 description 2
• 230000002159 abnormal effect Effects 0.000 description 2
• GOEMGAFJFRBGGG-UHFFFAOYSA-N acebutolol Chemical compound CCCC(=O)NC1=CC=C(OCC(O)CNC(C)C)C(C(C)=O)=C1 GOEMGAFJFRBGGG-UHFFFAOYSA-N 0.000 description 2
• 229940062352 aceon Drugs 0.000 description 2
• DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
• 229960001138 acetylsalicylic acid Drugs 0.000 description 2
• 150000007513 acids Chemical class 0.000 description 2
• DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
• 230000009471 action Effects 0.000 description 2
• 230000001154 acute effect Effects 0.000 description 2
• 229940092980 adalat Drugs 0.000 description 2
• 239000000556 agonist Substances 0.000 description 2
• NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 description 2
• 150000003973 alkyl amines Chemical class 0.000 description 2
• CJCSPKMFHVPWAR-JTQLQIEISA-N alpha-methyl-L-dopa Chemical compound OC(=O)[C@](N)(C)CC1=CC=C(O)C(O)=C1 CJCSPKMFHVPWAR-JTQLQIEISA-N 0.000 description 2
• 150000001408 amides Chemical class 0.000 description 2
• 150000001414 amino alcohols Chemical class 0.000 description 2
• IYIKLHRQXLHMJQ-UHFFFAOYSA-N amiodarone Chemical compound CCCCC=1OC2=CC=CC=C2C=1C(=O)C1=CC(I)=C(OCCN(CC)CC)C(I)=C1 IYIKLHRQXLHMJQ-UHFFFAOYSA-N 0.000 description 2
• 229960005260 amiodarone Drugs 0.000 description 2
• KRMDCWKBEZIMAB-UHFFFAOYSA-N amitriptyline Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 KRMDCWKBEZIMAB-UHFFFAOYSA-N 0.000 description 2
• HTIQEAQVCYTUBX-UHFFFAOYSA-N amlodipine Chemical compound CCOC(=O)C1=C(COCCN)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl HTIQEAQVCYTUBX-UHFFFAOYSA-N 0.000 description 2
• 230000000844 anti-bacterial effect Effects 0.000 description 2
• 239000003429 antifungal agent Substances 0.000 description 2
• 229940121375 antifungal agent Drugs 0.000 description 2
• 230000001746 atrial effect Effects 0.000 description 2
• 210000003050 axon Anatomy 0.000 description 2
• IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
• UIEATEWHFDRYRU-UHFFFAOYSA-N bepridil Chemical compound C1CCCN1C(COCC(C)C)CN(C=1C=CC=CC=1)CC1=CC=CC=C1 UIEATEWHFDRYRU-UHFFFAOYSA-N 0.000 description 2
• NWIUTZDMDHAVTP-UHFFFAOYSA-N betaxolol Chemical compound C1=CC(OCC(O)CNC(C)C)=CC=C1CCOCC1CC1 NWIUTZDMDHAVTP-UHFFFAOYSA-N 0.000 description 2
• 229960000516 bezafibrate Drugs 0.000 description 2
• IIBYAHWJQTYFKB-UHFFFAOYSA-N bezafibrate Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1CCNC(=O)C1=CC=C(Cl)C=C1 IIBYAHWJQTYFKB-UHFFFAOYSA-N 0.000 description 2
• 230000004071 biological effect Effects 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
• OIRCOABEOLEUMC-GEJPAHFPSA-N bivalirudin Chemical compound C([C@@H](C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CC(C)C)C(O)=O)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@H](CC(N)=O)NC(=O)CNC(=O)CNC(=O)CNC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](N)CC=1C=CC=CC=1)C1=CC=CC=C1 OIRCOABEOLEUMC-GEJPAHFPSA-N 0.000 description 2
• 108010055460 bivalirudin Proteins 0.000 description 2
• 230000017531 blood circulation Effects 0.000 description 2
• 230000036772 blood pressure Effects 0.000 description 2
• 230000036471 bradycardia Effects 0.000 description 2
• MAEIEVLCKWDQJH-UHFFFAOYSA-N bumetanide Chemical compound CCCCNC1=CC(C(O)=O)=CC(S(N)(=O)=O)=C1OC1=CC=CC=C1 MAEIEVLCKWDQJH-UHFFFAOYSA-N 0.000 description 2
• 235000019282 butylated hydroxyanisole Nutrition 0.000 description 2
• CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 2
• 229940043253 butylated hydroxyanisole Drugs 0.000 description 2
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
• HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Chemical compound [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 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
• 229940088033 calan Drugs 0.000 description 2
• 244000309466 calf Species 0.000 description 2
• FAKRSMQSSFJEIM-RQJHMYQMSA-N captopril Chemical compound SC[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O FAKRSMQSSFJEIM-RQJHMYQMSA-N 0.000 description 2
• 239000001768 carboxy methyl cellulose Substances 0.000 description 2
• 239000002327 cardiovascular agent Substances 0.000 description 2
• 229940125692 cardiovascular agent Drugs 0.000 description 2
• 229940088029 cardizem Drugs 0.000 description 2
• LWAFSWPYPHEXKX-UHFFFAOYSA-N carteolol Chemical compound N1C(=O)CCC2=C1C=CC=C2OCC(O)CNC(C)(C)C LWAFSWPYPHEXKX-UHFFFAOYSA-N 0.000 description 2
• OGHNVEJMJSYVRP-UHFFFAOYSA-N carvedilol Chemical compound COC1=CC=CC=C1OCCNCC(O)COC1=CC=CC2=C1C1=CC=CC=C1N2 OGHNVEJMJSYVRP-UHFFFAOYSA-N 0.000 description 2
• 229940063628 catapres Drugs 0.000 description 2
• QYIYFLOTGYLRGG-GPCCPHFNSA-N cefaclor Chemical compound C1([C@H](C(=O)N[C@@H]2C(N3C(=C(Cl)CS[C@@H]32)C(O)=O)=O)N)=CC=CC=C1 QYIYFLOTGYLRGG-GPCCPHFNSA-N 0.000 description 2
• 229960005361 cefaclor Drugs 0.000 description 2
• OKBVVJOGVLARMR-QSWIMTSFSA-N cefixime Chemical compound S1C(N)=NC(C(=N\OCC(O)=O)\C(=O)N[C@@H]2C(N3C(=C(C=C)CS[C@@H]32)C(O)=O)=O)=C1 OKBVVJOGVLARMR-QSWIMTSFSA-N 0.000 description 2
• LTINZAODLRIQIX-FBXRGJNPSA-N cefpodoxime proxetil Chemical compound N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC)C(=O)OC(C)OC(=O)OC(C)C)C(=O)C(=N/OC)\C1=CSC(N)=N1 LTINZAODLRIQIX-FBXRGJNPSA-N 0.000 description 2
• UNJFKXSSGBWRBZ-BJCIPQKHSA-N ceftibuten Chemical compound S1C(N)=NC(C(=C\CC(O)=O)\C(=O)N[C@@H]2C(N3C(=CCS[C@@H]32)C(O)=O)=O)=C1 UNJFKXSSGBWRBZ-BJCIPQKHSA-N 0.000 description 2
• 229960001668 cefuroxime Drugs 0.000 description 2
• JFPVXVDWJQMJEE-IZRZKJBUSA-N cefuroxime Chemical compound N([C@@H]1C(N2C(=C(COC(N)=O)CS[C@@H]21)C(O)=O)=O)C(=O)\C(=N/OC)C1=CC=CO1 JFPVXVDWJQMJEE-IZRZKJBUSA-N 0.000 description 2
• 235000010980 cellulose Nutrition 0.000 description 2
• 229920002678 cellulose Polymers 0.000 description 2
• 239000001913 cellulose Substances 0.000 description 2
• ZAIPMKNFIOOWCQ-UEKVPHQBSA-N cephalexin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CC=CC=C1 ZAIPMKNFIOOWCQ-UEKVPHQBSA-N 0.000 description 2
• RDLPVSKMFDYCOR-UEKVPHQBSA-N cephradine Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CCC=CC1 RDLPVSKMFDYCOR-UEKVPHQBSA-N 0.000 description 2
• 210000004978 chinese hamster ovary cell Anatomy 0.000 description 2
• 229910052801 chlorine Inorganic materials 0.000 description 2
• OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
• KPSRODZRAIWAKH-UHFFFAOYSA-N ciprofibrate Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1C1C(Cl)(Cl)C1 KPSRODZRAIWAKH-UHFFFAOYSA-N 0.000 description 2
• MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 description 2
• 229960002896 clonidine Drugs 0.000 description 2
• 229960002925 clonidine hydrochloride Drugs 0.000 description 2
• 238000004440 column chromatography Methods 0.000 description 2
• 229940125773 compound 10 Drugs 0.000 description 2
• 229940127113 compound 57 Drugs 0.000 description 2
• 238000013270 controlled release Methods 0.000 description 2
• 229920001577 copolymer Polymers 0.000 description 2
• 229940097488 corgard Drugs 0.000 description 2
• 235000005687 corn oil Nutrition 0.000 description 2
• 239000002285 corn oil Substances 0.000 description 2
• 238000012937 correction Methods 0.000 description 2
• 230000008878 coupling Effects 0.000 description 2
• 238000010168 coupling process Methods 0.000 description 2
• 238000005859 coupling reaction Methods 0.000 description 2
• 125000004122 cyclic group Chemical group 0.000 description 2
• 238000007405 data analysis Methods 0.000 description 2
• 230000003247 decreasing effect Effects 0.000 description 2
• NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 2
• 238000011161 development Methods 0.000 description 2
• 125000005265 dialkylamine group Chemical group 0.000 description 2
• 229960004166 diltiazem Drugs 0.000 description 2
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
• 208000035475 disorder Diseases 0.000 description 2
• 239000002612 dispersion medium Substances 0.000 description 2
• 238000009826 distribution Methods 0.000 description 2
• VJECBOKJABCYMF-UHFFFAOYSA-N doxazosin mesylate Chemical compound [H+].CS([O-])(=O)=O.C1OC2=CC=CC=C2OC1C(=O)N(CC1)CCN1C1=NC(N)=C(C=C(C(OC)=C2)OC)C2=N1 VJECBOKJABCYMF-UHFFFAOYSA-N 0.000 description 2
• 230000002526 effect on cardiovascular system Effects 0.000 description 2
• 230000007831 electrophysiology Effects 0.000 description 2
• 238000002001 electrophysiology Methods 0.000 description 2
• 239000000839 emulsion Substances 0.000 description 2
• GBXSMTUPTTWBMN-XIRDDKMYSA-N enalapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)CC1=CC=CC=C1 GBXSMTUPTTWBMN-XIRDDKMYSA-N 0.000 description 2
• 229960000873 enalapril Drugs 0.000 description 2
• OYFJQPXVCSSHAI-QFPUQLAESA-N enalapril maleate Chemical compound OC(=O)\C=C/C(O)=O.C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)CC1=CC=CC=C1 OYFJQPXVCSSHAI-QFPUQLAESA-N 0.000 description 2
• 239000012055 enteric layer Substances 0.000 description 2
• JUKPWJGBANNWMW-VWBFHTRKSA-N eplerenone Chemical compound C([C@@H]1[C@]2(C)C[C@H]3O[C@]33[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)C(=O)OC)C[C@@]21CCC(=O)O1 JUKPWJGBANNWMW-VWBFHTRKSA-N 0.000 description 2
• OROAFUQRIXKEMV-LDADJPATSA-N eprosartan Chemical compound C=1C=C(C(O)=O)C=CC=1CN1C(CCCC)=NC=C1\C=C(C(O)=O)/CC1=CC=CS1 OROAFUQRIXKEMV-LDADJPATSA-N 0.000 description 2
• WSEQXVZVJXJVFP-FQEVSTJZSA-N escitalopram Chemical compound C1([C@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-FQEVSTJZSA-N 0.000 description 2
• AQNDDEOPVVGCPG-UHFFFAOYSA-N esmolol Chemical compound COC(=O)CCC1=CC=C(OCC(O)CNC(C)C)C=C1 AQNDDEOPVVGCPG-UHFFFAOYSA-N 0.000 description 2
• 239000000945 filler Substances 0.000 description 2
• 238000001914 filtration Methods 0.000 description 2
• 238000003818 flash chromatography Methods 0.000 description 2
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
• 229910052731 fluorine Inorganic materials 0.000 description 2
• 239000011737 fluorine Substances 0.000 description 2
• 235000019253 formic acid Nutrition 0.000 description 2
• 239000012458 free base Substances 0.000 description 2
• 208000021302 gastroesophageal reflux disease Diseases 0.000 description 2
• 239000008273 gelatin Substances 0.000 description 2
• 229920000159 gelatin Polymers 0.000 description 2
• 229940014259 gelatin Drugs 0.000 description 2
• 235000019322 gelatine Nutrition 0.000 description 2
• 235000011852 gelatine desserts Nutrition 0.000 description 2
• 238000007429 general method Methods 0.000 description 2
• 239000008103 glucose Substances 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
• 230000005484 gravity Effects 0.000 description 2
• 208000019622 heart disease Diseases 0.000 description 2
• BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
• 229960002474 hydralazine Drugs 0.000 description 2
• 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 2
• 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 2
• 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 2
• MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 2
• 238000000338 in vitro Methods 0.000 description 2
• PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
• 229940095990 inderal Drugs 0.000 description 2
• 230000000053 inderal effect Effects 0.000 description 2
• CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
• 150000007529 inorganic bases Chemical class 0.000 description 2
• NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 2
• 229910052740 iodine Chemical group 0.000 description 2
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
• 229940088024 isoptin Drugs 0.000 description 2
• AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
• 230000000155 isotopic effect Effects 0.000 description 2
• ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 2
• 210000003734 kidney Anatomy 0.000 description 2
• 229960001632 labetalol Drugs 0.000 description 2
• MJIHNNLFOKEZEW-UHFFFAOYSA-N lansoprazole Chemical compound CC1=C(OCC(F)(F)F)C=CN=C1CS(=O)C1=NC2=CC=CC=C2N1 MJIHNNLFOKEZEW-UHFFFAOYSA-N 0.000 description 2
• 229960002394 lisinopril Drugs 0.000 description 2
• 229960001977 loracarbef Drugs 0.000 description 2
• JAPHQRWPEGVNBT-UTUOFQBUSA-M loracarbef anion Chemical compound C1([C@H](C(=O)N[C@@H]2C(N3C(=C(Cl)CC[C@@H]32)C([O-])=O)=O)N)=CC=CC=C1 JAPHQRWPEGVNBT-UTUOFQBUSA-M 0.000 description 2
• PSIFNNKUMBGKDQ-UHFFFAOYSA-N losartan Chemical compound CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C=2NN=NN=2)C=C1 PSIFNNKUMBGKDQ-UHFFFAOYSA-N 0.000 description 2
• 239000000314 lubricant Substances 0.000 description 2
• 239000011777 magnesium Substances 0.000 description 2
• 229910052749 magnesium Inorganic materials 0.000 description 2
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
• 235000019341 magnesium sulphate Nutrition 0.000 description 2
• 238000004519 manufacturing process Methods 0.000 description 2
• 238000004949 mass spectrometry Methods 0.000 description 2
• 239000002609 medium Substances 0.000 description 2
• 230000028161 membrane depolarization Effects 0.000 description 2
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
• KTMKRRPZPWUYKK-UHFFFAOYSA-N methylboronic acid Chemical compound CB(O)O KTMKRRPZPWUYKK-UHFFFAOYSA-N 0.000 description 2
• LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
• AQCHWTWZEMGIFD-UHFFFAOYSA-N metolazone Chemical compound CC1NC2=CC(Cl)=C(S(N)(=O)=O)C=C2C(=O)N1C1=CC=CC=C1C AQCHWTWZEMGIFD-UHFFFAOYSA-N 0.000 description 2
• 244000005700 microbiome Species 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
• 229940064639 minipress Drugs 0.000 description 2
• 229960003632 minoxidil Drugs 0.000 description 2
• 238000002156 mixing Methods 0.000 description 2
• BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
• 210000004165 myocardium Anatomy 0.000 description 2
• IFVOVTROPWIOLI-UHFFFAOYSA-N n-(2-oxopropyl)-2-[3-oxo-6-[4-(trifluoromethyl)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-2-yl]acetamide Chemical compound C=1N2C(=O)N(CC(=O)NCC(=O)C)N=C2C=CC=1C1=CC=C(C(F)(F)F)C=C1 IFVOVTROPWIOLI-UHFFFAOYSA-N 0.000 description 2
• LPOIGVZLNWEGJG-UHFFFAOYSA-N n-benzyl-5-(4-methylpiperazin-1-yl)-2-nitroaniline Chemical compound C1CN(C)CCN1C1=CC=C([N+]([O-])=O)C(NCC=2C=CC=CC=2)=C1 LPOIGVZLNWEGJG-UHFFFAOYSA-N 0.000 description 2
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
• 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
• 229960004255 nadolol Drugs 0.000 description 2
• 125000001624 naphthyl group Chemical group 0.000 description 2
• 238000002663 nebulization Methods 0.000 description 2
• SGXXNSQHWDMGGP-IZZDOVSWSA-N nizatidine Chemical compound [O-][N+](=O)\C=C(/NC)NCCSCC1=CSC(CN(C)C)=N1 SGXXNSQHWDMGGP-IZZDOVSWSA-N 0.000 description 2
• 150000007524 organic acids Chemical class 0.000 description 2
• 150000007530 organic bases Chemical class 0.000 description 2
• 239000002245 particle Substances 0.000 description 2
• 230000008506 pathogenesis Effects 0.000 description 2
• 229960002582 perindopril Drugs 0.000 description 2
• IPVQLZZIHOAWMC-QXKUPLGCSA-N perindopril Chemical compound C1CCC[C@H]2C[C@@H](C(O)=O)N(C(=O)[C@H](C)N[C@@H](CCC)C(=O)OCC)[C@H]21 IPVQLZZIHOAWMC-QXKUPLGCSA-N 0.000 description 2
• IYNMDWMQHSMDDE-MHXJNQAMSA-N perindopril erbumine Chemical compound CC(C)(C)N.C1CCC[C@@H]2N(C(=O)[C@H](C)N[C@@H](CCC)C(=O)OCC)[C@H](C(O)=O)C[C@@H]21 IYNMDWMQHSMDDE-MHXJNQAMSA-N 0.000 description 2
• 208000030613 peripheral artery disease Diseases 0.000 description 2
• 239000008177 pharmaceutical agent Substances 0.000 description 2
• RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 2
• 229910052698 phosphorus Inorganic materials 0.000 description 2
• 239000011574 phosphorus Substances 0.000 description 2
• JZQKKSLKJUAGIC-UHFFFAOYSA-N pindolol Chemical compound CC(C)NCC(O)COC1=CC=CC2=C1C=CN2 JZQKKSLKJUAGIC-UHFFFAOYSA-N 0.000 description 2
• 239000013612 plasmid Substances 0.000 description 2
• 238000002600 positron emission tomography Methods 0.000 description 2
• 239000011591 potassium Substances 0.000 description 2
• 229910052700 potassium Inorganic materials 0.000 description 2
• 239000004036 potassium channel stimulating agent Substances 0.000 description 2
• 229940089949 procardia Drugs 0.000 description 2
• 230000008569 process Effects 0.000 description 2
• 238000012545 processing Methods 0.000 description 2
• 229960003712 propranolol Drugs 0.000 description 2
• 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
• QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
• 108090000623 proteins and genes Proteins 0.000 description 2
• CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 2
• LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 description 2
• XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
• 150000003254 radicals Chemical class 0.000 description 2
• QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 2
• YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
• 238000002603 single-photon emission computed tomography Methods 0.000 description 2
• WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 2
• 239000004299 sodium benzoate Substances 0.000 description 2
• 235000010234 sodium benzoate Nutrition 0.000 description 2
• 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
• 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
• DAEPDZWVDSPTHF-UHFFFAOYSA-M sodium pyruvate Chemical compound [Na+].CC(=O)C([O-])=O DAEPDZWVDSPTHF-UHFFFAOYSA-M 0.000 description 2
• 239000008247 solid mixture Substances 0.000 description 2
• LXMSZDCAJNLERA-ZHYRCANASA-N spironolactone Chemical compound C([C@@H]1[C@]2(C)CC[C@@H]3[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)SC(=O)C)C[C@@]21CCC(=O)O1 LXMSZDCAJNLERA-ZHYRCANASA-N 0.000 description 2
• 239000008223 sterile water Substances 0.000 description 2
• 210000002784 stomach Anatomy 0.000 description 2
• UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
• 238000007920 subcutaneous administration Methods 0.000 description 2
• 239000000126 substance Substances 0.000 description 2
• 125000004426 substituted alkynyl group Chemical group 0.000 description 2
• 238000006467 substitution reaction Methods 0.000 description 2
• 150000003457 sulfones Chemical class 0.000 description 2
• 150000003462 sulfoxides Chemical class 0.000 description 2
• 239000013589 supplement Substances 0.000 description 2
• 239000000829 suppository Substances 0.000 description 2
• 239000006188 syrup Substances 0.000 description 2
• 235000020357 syrup Nutrition 0.000 description 2
• 230000006794 tachycardia Effects 0.000 description 2
• VCKUSRYTPJJLNI-UHFFFAOYSA-N terazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1CCCO1 VCKUSRYTPJJLNI-UHFFFAOYSA-N 0.000 description 2
• IMCGHZIGRANKHV-AJNGGQMLSA-N tert-butyl (3s,5s)-2-oxo-5-[(2s,4s)-5-oxo-4-propan-2-yloxolan-2-yl]-3-propan-2-ylpyrrolidine-1-carboxylate Chemical compound O1C(=O)[C@H](C(C)C)C[C@H]1[C@H]1N(C(=O)OC(C)(C)C)C(=O)[C@H](C(C)C)C1 IMCGHZIGRANKHV-AJNGGQMLSA-N 0.000 description 2
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
• 238000010998 test method Methods 0.000 description 2
• 229960002180 tetracycline Drugs 0.000 description 2
• 229930101283 tetracycline Natural products 0.000 description 2
• 235000019364 tetracycline Nutrition 0.000 description 2
• 150000003522 tetracyclines Chemical class 0.000 description 2
• YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 description 2
• ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 2
• 238000004809 thin layer chromatography Methods 0.000 description 2
• 229960004605 timolol Drugs 0.000 description 2
• 229960000187 tissue plasminogen activator Drugs 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
• 239000003053 toxin Substances 0.000 description 2
• 231100000765 toxin Toxicity 0.000 description 2
• 229940108522 trandate Drugs 0.000 description 2
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
• PHLBKPHSAVXXEF-UHFFFAOYSA-N trazodone Chemical compound ClC1=CC=CC(N2CCN(CCCN3C(N4C=CC=CC4=N3)=O)CC2)=C1 PHLBKPHSAVXXEF-UHFFFAOYSA-N 0.000 description 2
• 125000005270 trialkylamine group Chemical group 0.000 description 2
• GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
• 229940099270 vasotec Drugs 0.000 description 2
• 210000003462 vein Anatomy 0.000 description 2
• PNVNVHUZROJLTJ-UHFFFAOYSA-N venlafaxine Chemical compound C1=CC(OC)=CC=C1C(CN(C)C)C1(O)CCCCC1 PNVNVHUZROJLTJ-UHFFFAOYSA-N 0.000 description 2
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
• PJVWKTKQMONHTI-UHFFFAOYSA-N warfarin Chemical compound OC=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 PJVWKTKQMONHTI-UHFFFAOYSA-N 0.000 description 2
• 238000005406 washing Methods 0.000 description 2
• 239000000230 xanthan gum Substances 0.000 description 2
• 235000010493 xanthan gum Nutrition 0.000 description 2
• 229920001285 xanthan gum Polymers 0.000 description 2
• 229940082509 xanthan gum Drugs 0.000 description 2
• 229940072252 zestril Drugs 0.000 description 2
• VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
• UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 1
• AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 1
• GKEMHVLBZNVZOI-SJKOYZFVSA-N (1r,2r)-n-methyl-1-oxo-2-pyridin-3-ylthiane-2-carbothioamide Chemical compound C=1C=CN=CC=1[C@@]1(C(=S)NC)CCCC[S@]1=O GKEMHVLBZNVZOI-SJKOYZFVSA-N 0.000 description 1
• ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 1
• KTGRHKOEFSJQNS-BDQAORGHSA-N (1s)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3h-2-benzofuran-5-carbonitrile;oxalic acid Chemical compound OC(=O)C(O)=O.C1([C@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 KTGRHKOEFSJQNS-BDQAORGHSA-N 0.000 description 1
• SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 1
• QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
• GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
• IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 description 1
• YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 description 1
• VIJSPAIQWVPKQZ-BLECARSGSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-4-methylpentanoyl]amino]-4,4-dimethylpentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(C)=O VIJSPAIQWVPKQZ-BLECARSGSA-N 0.000 description 1
• YKFCISHFRZHKHY-NGQGLHOPSA-N (2s)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid;trihydrate Chemical compound O.O.O.OC(=O)[C@](N)(C)CC1=CC=C(O)C(O)=C1.OC(=O)[C@](N)(C)CC1=CC=C(O)C(O)=C1 YKFCISHFRZHKHY-NGQGLHOPSA-N 0.000 description 1
• STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 description 1
• QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
• IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 1
• UDQTXCHQKHIQMH-KYGLGHNPSA-N (3ar,5s,6s,7r,7ar)-5-(difluoromethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](C(F)F)[C@@H](O)[C@@H]2O UDQTXCHQKHIQMH-KYGLGHNPSA-N 0.000 description 1
• DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
• OOKAZRDERJMRCJ-KOUAFAAESA-N (3r)-7-[(1s,2s,4ar,6s,8s)-2,6-dimethyl-8-[(2s)-2-methylbutanoyl]oxy-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-hydroxy-5-oxoheptanoic acid Chemical compound C1=C[C@H](C)[C@H](CCC(=O)C[C@@H](O)CC(O)=O)C2[C@@H](OC(=O)[C@@H](C)CC)C[C@@H](C)C[C@@H]21 OOKAZRDERJMRCJ-KOUAFAAESA-N 0.000 description 1
• HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 description 1
• MPDDTAJMJCESGV-CTUHWIOQSA-M (3r,5r)-7-[2-(4-fluorophenyl)-5-[methyl-[(1r)-1-phenylethyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoate Chemical compound C1([C@@H](C)N(C)C(=O)C2=NN(C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C2C(C)C)C=2C=CC(F)=CC=2)=CC=CC=C1 MPDDTAJMJCESGV-CTUHWIOQSA-M 0.000 description 1
• MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-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
• MMSFHQSHXRMPLJ-CVEARBPZSA-N (3s,4r)-3-hydroxy-2,2-dimethyl-4-(2-oxopyridin-1-yl)-3,4-dihydrochromene-6-carbonitrile Chemical compound N1([C@@H]2C3=CC(=CC=C3OC([C@H]2O)(C)C)C#N)C=CC=CC1=O MMSFHQSHXRMPLJ-CVEARBPZSA-N 0.000 description 1
• YQOLEILXOBUDMU-KRWDZBQOSA-N (4R)-5-[(6-bromo-3-methyl-2-pyrrolidin-1-ylquinoline-4-carbonyl)amino]-4-(2-chlorophenyl)pentanoic acid Chemical compound CC1=C(C2=C(C=CC(=C2)Br)N=C1N3CCCC3)C(=O)NC[C@H](CCC(=O)O)C4=CC=CC=C4Cl YQOLEILXOBUDMU-KRWDZBQOSA-N 0.000 description 1
• ZFLWDHHVRRZMEI-ZDUSSCGKSA-N (4S)-2,6-dimethyl-5-nitro-4-[2-(trifluoromethyl)phenyl]-1,4-dihydropyridine-3-carboxylic acid methyl ester Chemical compound COC(=O)C1=C(C)NC(C)=C([N+]([O-])=O)[C@H]1C1=CC=CC=C1C(F)(F)F ZFLWDHHVRRZMEI-ZDUSSCGKSA-N 0.000 description 1
• STPKWKPURVSAJF-LJEWAXOPSA-N (4r,5r)-5-[4-[[4-(1-aza-4-azoniabicyclo[2.2.2]octan-4-ylmethyl)phenyl]methoxy]phenyl]-3,3-dibutyl-7-(dimethylamino)-1,1-dioxo-4,5-dihydro-2h-1$l^{6}-benzothiepin-4-ol Chemical compound O[C@H]1C(CCCC)(CCCC)CS(=O)(=O)C2=CC=C(N(C)C)C=C2[C@H]1C(C=C1)=CC=C1OCC(C=C1)=CC=C1C[N+]1(CC2)CCN2CC1 STPKWKPURVSAJF-LJEWAXOPSA-N 0.000 description 1
• XCOCAEQWLWCICR-UHFFFAOYSA-N (5-cyclopropyl-2-methylpyrazol-3-yl)methanol Chemical compound C1=C(CO)N(C)N=C1C1CC1 XCOCAEQWLWCICR-UHFFFAOYSA-N 0.000 description 1
• OIIOPWHTJZYKIL-PMACEKPBSA-N (5S)-5-[[[5-[2-chloro-3-[2-chloro-3-[6-methoxy-5-[[[(2S)-5-oxopyrrolidin-2-yl]methylamino]methyl]pyrazin-2-yl]phenyl]phenyl]-3-methoxypyrazin-2-yl]methylamino]methyl]pyrrolidin-2-one Chemical compound C1(=C(N=C(C2=C(C(C3=CC=CC(=C3Cl)C3=NC(OC)=C(N=C3)CNC[C@H]3NC(=O)CC3)=CC=C2)Cl)C=N1)OC)CNC[C@H]1NC(=O)CC1 OIIOPWHTJZYKIL-PMACEKPBSA-N 0.000 description 1
• VUEGYUOUAAVYAS-JGGQBBKZSA-N (6ar,9s,10ar)-9-(dimethylsulfamoylamino)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline Chemical compound C1=CC([C@H]2C[C@@H](CN(C)[C@@H]2C2)NS(=O)(=O)N(C)C)=C3C2=CNC3=C1 VUEGYUOUAAVYAS-JGGQBBKZSA-N 0.000 description 1
• UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 1
• 229930182837 (R)-adrenaline Natural products 0.000 description 1
• METKIMKYRPQLGS-GFCCVEGCSA-N (R)-atenolol Chemical compound CC(C)NC[C@@H](O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-GFCCVEGCSA-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
• BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical class OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
• ZFHGXWPMULPQSE-SZGBIDFHSA-N (Z)-(1S)-cis-tefluthrin Chemical compound FC1=C(F)C(C)=C(F)C(F)=C1COC(=O)[C@@H]1C(C)(C)[C@@H]1\C=C(/Cl)C(F)(F)F ZFHGXWPMULPQSE-SZGBIDFHSA-N 0.000 description 1
• BRIPGNJWPCKDQZ-WXXKFALUSA-N (e)-but-2-enedioic acid;1-[4-(2-methoxyethyl)phenoxy]-3-(propan-2-ylamino)propan-2-ol Chemical compound OC(=O)\C=C\C(O)=O.COCCC1=CC=C(OCC(O)CNC(C)C)C=C1.COCCC1=CC=C(OCC(O)CNC(C)C)C=C1 BRIPGNJWPCKDQZ-WXXKFALUSA-N 0.000 description 1
• ZGYIXVSQHOKQRZ-COIATFDQSA-N (e)-n-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-3-cyano-7-[(3s)-oxolan-3-yl]oxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound N#CC1=CN=C2C=C(O[C@@H]3COCC3)C(NC(=O)/C=C/CN(C)C)=CC2=C1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 ZGYIXVSQHOKQRZ-COIATFDQSA-N 0.000 description 1
• MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 description 1
• DEVSOMFAQLZNKR-RJRFIUFISA-N (z)-3-[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-triazol-1-yl]-n'-pyrazin-2-ylprop-2-enehydrazide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C2=NN(\C=C/C(=O)NNC=3N=CC=NC=3)C=N2)=C1 DEVSOMFAQLZNKR-RJRFIUFISA-N 0.000 description 1
• WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
• CSVFWMMPUJDVKH-UHFFFAOYSA-N 1,1-dichloropropan-2-one Chemical compound CC(=O)C(Cl)Cl CSVFWMMPUJDVKH-UHFFFAOYSA-N 0.000 description 1
• 125000004505 1,2,4-oxadiazol-5-yl group Chemical group O1N=CN=C1* 0.000 description 1
• PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
• DJMOXMNDXFFONV-UHFFFAOYSA-N 1,3-dimethyl-7-[2-(n-methylanilino)ethyl]purine-2,6-dione Chemical compound C1=NC=2N(C)C(=O)N(C)C(=O)C=2N1CCN(C)C1=CC=CC=C1 DJMOXMNDXFFONV-UHFFFAOYSA-N 0.000 description 1
• KKHFRAFPESRGGD-UHFFFAOYSA-N 1,3-dimethyl-7-[3-(n-methylanilino)propyl]purine-2,6-dione Chemical compound C1=NC=2N(C)C(=O)N(C)C(=O)C=2N1CCCN(C)C1=CC=CC=C1 KKHFRAFPESRGGD-UHFFFAOYSA-N 0.000 description 1
• YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 description 1
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
• APWRZPQBPCAXFP-UHFFFAOYSA-N 1-(1-oxo-2H-isoquinolin-5-yl)-5-(trifluoromethyl)-N-[2-(trifluoromethyl)pyridin-4-yl]pyrazole-4-carboxamide Chemical compound O=C1NC=CC2=C(C=CC=C12)N1N=CC(=C1C(F)(F)F)C(=O)NC1=CC(=NC=C1)C(F)(F)F APWRZPQBPCAXFP-UHFFFAOYSA-N 0.000 description 1
• OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 1
• KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 1
• WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 1
• ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 1
• ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 1
• WSEQXVZVJXJVFP-UHFFFAOYSA-N 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile Chemical compound O1CC2=CC(C#N)=CC=C2C1(CCCN(C)C)C1=CC=C(F)C=C1 WSEQXVZVJXJVFP-UHFFFAOYSA-N 0.000 description 1
• WIHMBLDNRMIGDW-UHFFFAOYSA-N 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3h-2-benzofuran-5-carbonitrile;hydron;bromide Chemical compound [Br-].O1CC2=CC(C#N)=CC=C2C1(CCC[NH+](C)C)C1=CC=C(F)C=C1 WIHMBLDNRMIGDW-UHFFFAOYSA-N 0.000 description 1
• HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
• RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
• IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
• TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 1
• BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
• JTVSKASWNROQQF-UHFFFAOYSA-N 2,2-dimethyl-4-(2-oxopyridin-1-yl)chromene-6-carbonitrile Chemical compound C=1C(C)(C)OC2=CC=C(C#N)C=C2C=1N1C=CC=CC1=O JTVSKASWNROQQF-UHFFFAOYSA-N 0.000 description 1
• VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 1
• WGFNXGPBPIJYLI-UHFFFAOYSA-N 2,6-difluoro-3-[(3-fluorophenyl)sulfonylamino]-n-(3-methoxy-1h-pyrazolo[3,4-b]pyridin-5-yl)benzamide Chemical compound C1=C2C(OC)=NNC2=NC=C1NC(=O)C(C=1F)=C(F)C=CC=1NS(=O)(=O)C1=CC=CC(F)=C1 WGFNXGPBPIJYLI-UHFFFAOYSA-N 0.000 description 1
• WVCRMSJBMLAUEK-UHFFFAOYSA-N 2-(1,2,4-oxadiazol-3-ylmethyl)-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CC3=NOC=N3)N=C2C=C1 WVCRMSJBMLAUEK-UHFFFAOYSA-N 0.000 description 1
• FQMZXMVHHKXGTM-UHFFFAOYSA-N 2-(1-adamantyl)-n-[2-[2-(2-hydroxyethylamino)ethylamino]quinolin-5-yl]acetamide Chemical compound C1C(C2)CC(C3)CC2CC13CC(=O)NC1=CC=CC2=NC(NCCNCCO)=CC=C21 FQMZXMVHHKXGTM-UHFFFAOYSA-N 0.000 description 1
• QMJHNMSIIGRNOP-UHFFFAOYSA-N 2-(2,6-difluorophenyl)ethanol Chemical compound OCCC1=C(F)C=CC=C1F QMJHNMSIIGRNOP-UHFFFAOYSA-N 0.000 description 1
• VCUXVXLUOHDHKK-UHFFFAOYSA-N 2-(2-aminopyrimidin-4-yl)-4-(2-chloro-4-methoxyphenyl)-1,3-thiazole-5-carboxamide Chemical compound ClC1=CC(OC)=CC=C1C1=C(C(N)=O)SC(C=2N=C(N)N=CC=2)=N1 VCUXVXLUOHDHKK-UHFFFAOYSA-N 0.000 description 1
• QEBYEVQKHRUYPE-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-[(1-methylpyrazol-3-yl)methyl]-4-[[methyl(pyridin-3-ylmethyl)amino]methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1=CN(C)N=C1CN1C(=O)C=C2NN(C=3C(=CC=CC=3)Cl)C(=O)C2=C1CN(C)CC1=CC=CN=C1 QEBYEVQKHRUYPE-UHFFFAOYSA-N 0.000 description 1
• GOTMMYATDXENID-UHFFFAOYSA-N 2-(2-hydroxyethyl)-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C=1N2C(=O)N(CCO)N=C2C=CC=1C1=CC=C(OC(F)(F)F)C=C1 GOTMMYATDXENID-UHFFFAOYSA-N 0.000 description 1
• KCHKHBADKQLXJX-UHFFFAOYSA-N 2-(2-methoxy-3-phenoxypropyl)-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound N1=C2C=CC(C=3C=CC(OC(F)(F)F)=CC=3)=CN2C(=O)N1CC(OC)COC1=CC=CC=C1 KCHKHBADKQLXJX-UHFFFAOYSA-N 0.000 description 1
• WOANLVBXUYDEGP-UHFFFAOYSA-N 2-(2-pyrimidin-2-yloxyethyl)-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCOC=3N=CC=CN=3)N=C2C=C1 WOANLVBXUYDEGP-UHFFFAOYSA-N 0.000 description 1
• JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
• MZBYMEWBOVJKJG-UHFFFAOYSA-N 2-[(1-methylpyrazol-3-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CN1C=CC(CN2C(N3C=C(C=CC3=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=N1 MZBYMEWBOVJKJG-UHFFFAOYSA-N 0.000 description 1
• QCEYKMMEGNHVKQ-UHFFFAOYSA-N 2-[(2-cyclopropyl-1,3-oxazol-4-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CC=3N=C(OC=3)C3CC3)N=C2C=C1 QCEYKMMEGNHVKQ-UHFFFAOYSA-N 0.000 description 1
• APBITVXQWUFSQW-UHFFFAOYSA-N 2-[(3,5-dimethyl-1,2-oxazol-4-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CC1=NOC(C)=C1CN1C(=O)N2C=C(C=3C=CC(OC(F)(F)F)=CC=3)C=CC2=N1 APBITVXQWUFSQW-UHFFFAOYSA-N 0.000 description 1
• BTIBQACUUFVHNX-UHFFFAOYSA-N 2-[(3-benzyl-1,2,4-oxadiazol-5-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CC=3ON=C(CC=4C=CC=CC=4)N=3)N=C2C=C1 BTIBQACUUFVHNX-UHFFFAOYSA-N 0.000 description 1
• GVLLPSKBAGVQRD-UHFFFAOYSA-N 2-[(3-methyl-1,2-oxazol-5-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound O1N=C(C)C=C1CN1C(=O)N2C=C(C=3C=CC(OC(F)(F)F)=CC=3)C=CC2=N1 GVLLPSKBAGVQRD-UHFFFAOYSA-N 0.000 description 1
• FBOKDLWWWSMXBH-UHFFFAOYSA-N 2-[(4-cyclopropyl-1,3-oxazol-2-yl)methyl]-6-[4-(trifluoromethyl)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CN2C(=O)N(CC=3OC=C(N=3)C3CC3)N=C2C=C1 FBOKDLWWWSMXBH-UHFFFAOYSA-N 0.000 description 1
• NGBGOTULLHICLU-UHFFFAOYSA-N 2-[(5-methyl-1,2,4-oxadiazol-3-yl)methyl]-6-(3-phenoxyphenyl)-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound O1C(C)=NC(CN2C(N3C=C(C=CC3=N2)C=2C=C(OC=3C=CC=CC=3)C=CC=2)=O)=N1 NGBGOTULLHICLU-UHFFFAOYSA-N 0.000 description 1
• CRTDEOBLJALPST-UHFFFAOYSA-N 2-[(5-methyl-1,2-oxazol-3-yl)methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound O1C(C)=CC(CN2C(N3C=C(C=CC3=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=N1 CRTDEOBLJALPST-UHFFFAOYSA-N 0.000 description 1
• XHFWNLUQGXEFMN-UHFFFAOYSA-N 2-[2-(4-bromopyridin-2-yl)ethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCC=3N=CC=C(Br)C=3)N=C2C=C1 XHFWNLUQGXEFMN-UHFFFAOYSA-N 0.000 description 1
• OXDREFSEJYBYLK-UHFFFAOYSA-N 2-[2-oxo-2-(3-phenoxypyrrolidin-1-yl)ethyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CC(=O)N3CC(CC3)OC=3C=CC=CC=3)N=C2C=C1 OXDREFSEJYBYLK-UHFFFAOYSA-N 0.000 description 1
• ZXSCJXXCGATRPV-UHFFFAOYSA-N 2-[3-(3-chlorophenoxy)propyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCCOC=3C=C(Cl)C=CC=3)N=C2C=C1 ZXSCJXXCGATRPV-UHFFFAOYSA-N 0.000 description 1
• BVYHHAKGJKNYQX-UHFFFAOYSA-N 2-[3-(4-chlorophenoxy)-2-methoxypropyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound N1=C2C=CC(C=3C=CC(OC(F)(F)F)=CC=3)=CN2C(=O)N1CC(OC)COC1=CC=C(Cl)C=C1 BVYHHAKGJKNYQX-UHFFFAOYSA-N 0.000 description 1
• ABNSLHCWHUQTLY-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)propyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCCC=3C=CC(Cl)=CC=3)N=C2C=C1 ABNSLHCWHUQTLY-UHFFFAOYSA-N 0.000 description 1
• ACSHSHRKPVCYFQ-UHFFFAOYSA-N 2-[3-oxo-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-2-yl]acetic acid Chemical compound C=1N2C(=O)N(CC(=O)O)N=C2C=CC=1C1=CC=C(OC(F)(F)F)C=C1 ACSHSHRKPVCYFQ-UHFFFAOYSA-N 0.000 description 1
• PYRKKGOKRMZEIT-UHFFFAOYSA-N 2-[6-(2-cyclopropylethoxy)-9-(2-hydroxy-2-methylpropyl)-1h-phenanthro[9,10-d]imidazol-2-yl]-5-fluorobenzene-1,3-dicarbonitrile Chemical compound C1=C2C3=CC(CC(C)(O)C)=CC=C3C=3NC(C=4C(=CC(F)=CC=4C#N)C#N)=NC=3C2=CC=C1OCCC1CC1 PYRKKGOKRMZEIT-UHFFFAOYSA-N 0.000 description 1
• FDRCWVQKOJFPSP-UHFFFAOYSA-N 2-[[3-(2,6-dichlorophenyl)-1,2,4-oxadiazol-5-yl]methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CC=3ON=C(N=3)C=3C(=CC=CC=3Cl)Cl)N=C2C=C1 FDRCWVQKOJFPSP-UHFFFAOYSA-N 0.000 description 1
• GECBYKRXMYAANX-UHFFFAOYSA-N 2-[[3-[[3-oxo-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-2-yl]methyl]-1,2,4-oxadiazol-5-yl]methyl]isoindole-1,3-dione Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CC=3N=C(CN4C(C5=CC=CC=C5C4=O)=O)ON=3)N=C2C=C1 GECBYKRXMYAANX-UHFFFAOYSA-N 0.000 description 1
• PAYROHWFGZADBR-UHFFFAOYSA-N 2-[[4-amino-5-(5-iodo-4-methoxy-2-propan-2-ylphenoxy)pyrimidin-2-yl]amino]propane-1,3-diol Chemical compound C1=C(I)C(OC)=CC(C(C)C)=C1OC1=CN=C(NC(CO)CO)N=C1N PAYROHWFGZADBR-UHFFFAOYSA-N 0.000 description 1
• FZKREWRQMQAHGF-UHFFFAOYSA-N 2-[[5-(pyridin-2-yloxymethyl)-1,2,4-oxadiazol-3-yl]methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CC=3N=C(COC=4N=CC=CC=4)ON=3)N=C2C=C1 FZKREWRQMQAHGF-UHFFFAOYSA-N 0.000 description 1
• CMHDTVBZJICYIX-UHFFFAOYSA-N 2-[[5-(pyrimidin-2-yloxymethyl)-1,2,4-oxadiazol-3-yl]methyl]-6-[4-(trifluoromethoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CC=3N=C(COC=4N=CC=CN=4)ON=3)N=C2C=C1 CMHDTVBZJICYIX-UHFFFAOYSA-N 0.000 description 1
• VVCMGAUPZIKYTH-VGHSCWAPSA-N 2-acetyloxybenzoic acid;[(2s,3r)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl] propanoate;1,3,7-trimethylpurine-2,6-dione Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O.CN1C(=O)N(C)C(=O)C2=C1N=CN2C.C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 VVCMGAUPZIKYTH-VGHSCWAPSA-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
• TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 1
• NPRYCHLHHVWLQZ-TURQNECASA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynylpurin-8-one Chemical compound NC1=NC=C2N(C(N(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C NPRYCHLHHVWLQZ-TURQNECASA-N 0.000 description 1
• FZRBTBCCMVNZBD-UHFFFAOYSA-N 2-chloro-4-(trifluoromethyl)pyrimidine Chemical compound FC(F)(F)C1=CC=NC(Cl)=N1 FZRBTBCCMVNZBD-UHFFFAOYSA-N 0.000 description 1
• JFZJMSDDOOAOIV-UHFFFAOYSA-N 2-chloro-5-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=C(Cl)N=C1 JFZJMSDDOOAOIV-UHFFFAOYSA-N 0.000 description 1
• JIVPVXMEBJLZRO-CQSZACIVSA-N 2-chloro-5-[(1r)-1-hydroxy-3-oxo-2h-isoindol-1-yl]benzenesulfonamide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC([C@@]2(O)C3=CC=CC=C3C(=O)N2)=C1 JIVPVXMEBJLZRO-CQSZACIVSA-N 0.000 description 1
• MTAODLNXWYIKSO-UHFFFAOYSA-N 2-fluoropyridine Chemical compound FC1=CC=CC=N1 MTAODLNXWYIKSO-UHFFFAOYSA-N 0.000 description 1
• LFOIDLOIBZFWDO-UHFFFAOYSA-N 2-methoxy-6-[6-methoxy-4-[(3-phenylmethoxyphenyl)methoxy]-1-benzofuran-2-yl]imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=C2SC(OC)=NN2C=C1C(OC1=CC(OC)=C2)=CC1=C2OCC(C=1)=CC=CC=1OCC1=CC=CC=C1 LFOIDLOIBZFWDO-UHFFFAOYSA-N 0.000 description 1
• VLRSADZEDXVUPG-UHFFFAOYSA-N 2-naphthalen-1-ylpyridine Chemical compound N1=CC=CC=C1C1=CC=CC2=CC=CC=C12 VLRSADZEDXVUPG-UHFFFAOYSA-N 0.000 description 1
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
• RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 1
• VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 1
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
• DFRAKBCRUYUFNT-UHFFFAOYSA-N 3,8-dicyclohexyl-2,4,7,9-tetrahydro-[1,3]oxazino[5,6-h][1,3]benzoxazine Chemical compound C1CCCCC1N1CC(C=CC2=C3OCN(C2)C2CCCCC2)=C3OC1 DFRAKBCRUYUFNT-UHFFFAOYSA-N 0.000 description 1
• HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 1
• BYHQTRFJOGIQAO-GOSISDBHSA-N 3-(4-bromophenyl)-8-[(2R)-2-hydroxypropyl]-1-[(3-methoxyphenyl)methyl]-1,3,8-triazaspiro[4.5]decan-2-one Chemical compound C[C@H](CN1CCC2(CC1)CN(C(=O)N2CC3=CC(=CC=C3)OC)C4=CC=C(C=C4)Br)O BYHQTRFJOGIQAO-GOSISDBHSA-N 0.000 description 1
• FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
• QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 1
• WFOVEDJTASPCIR-UHFFFAOYSA-N 3-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)methylamino]-n-[[2-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1CNC(C=1)=CC=CC=1C(=O)NCC1=CC=CC=C1C(F)(F)F WFOVEDJTASPCIR-UHFFFAOYSA-N 0.000 description 1
• WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 1
• SRVXSISGYBMIHR-UHFFFAOYSA-N 3-[3-[3-(2-amino-2-oxoethyl)phenyl]-5-chlorophenyl]-3-(5-methyl-1,3-thiazol-2-yl)propanoic acid Chemical compound S1C(C)=CN=C1C(CC(O)=O)C1=CC(Cl)=CC(C=2C=C(CC(N)=O)C=CC=2)=C1 SRVXSISGYBMIHR-UHFFFAOYSA-N 0.000 description 1
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical class NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
• QBCCQGAULNCGCX-UHFFFAOYSA-N 3-benzyl-5-[[6-[4-(trifluoromethoxy)phenyl]-3H-[1,2,4]triazolo[4,3-a]pyridin-2-yl]methyl]-1,2,4-oxadiazole Chemical compound C(C1=CC=CC=C1)C1=NOC(=N1)CN1N=C2N(C=C(C=C2)C2=CC=C(C=C2)OC(F)(F)F)C1 QBCCQGAULNCGCX-UHFFFAOYSA-N 0.000 description 1
• HAAFFTHBNFBVKY-UHFFFAOYSA-N 4,5-dichloro-2-methoxyphenol Chemical compound COC1=CC(Cl)=C(Cl)C=C1O HAAFFTHBNFBVKY-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
• YFCIFWOJYYFDQP-PTWZRHHISA-N 4-[3-amino-6-[(1S,3S,4S)-3-fluoro-4-hydroxycyclohexyl]pyrazin-2-yl]-N-[(1S)-1-(3-bromo-5-fluorophenyl)-2-(methylamino)ethyl]-2-fluorobenzamide Chemical compound CNC[C@@H](NC(=O)c1ccc(cc1F)-c1nc(cnc1N)[C@H]1CC[C@H](O)[C@@H](F)C1)c1cc(F)cc(Br)c1 YFCIFWOJYYFDQP-PTWZRHHISA-N 0.000 description 1
• WYFCZWSWFGJODV-MIANJLSGSA-N 4-[[(1s)-2-[(e)-3-[3-chloro-2-fluoro-6-(tetrazol-1-yl)phenyl]prop-2-enoyl]-5-(4-methyl-2-oxopiperazin-1-yl)-3,4-dihydro-1h-isoquinoline-1-carbonyl]amino]benzoic acid Chemical compound O=C1CN(C)CCN1C1=CC=CC2=C1CCN(C(=O)\C=C\C=1C(=CC=C(Cl)C=1F)N1N=NN=C1)[C@@H]2C(=O)NC1=CC=C(C(O)=O)C=C1 WYFCZWSWFGJODV-MIANJLSGSA-N 0.000 description 1
• MPMKMQHJHDHPBE-RUZDIDTESA-N 4-[[(2r)-1-(1-benzothiophene-3-carbonyl)-2-methylazetidine-2-carbonyl]-[(3-chlorophenyl)methyl]amino]butanoic acid Chemical compound O=C([C@@]1(N(CC1)C(=O)C=1C2=CC=CC=C2SC=1)C)N(CCCC(O)=O)CC1=CC=CC(Cl)=C1 MPMKMQHJHDHPBE-RUZDIDTESA-N 0.000 description 1
• KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
• GSDQYSSLIKJJOG-UHFFFAOYSA-N 4-chloro-2-(3-chloroanilino)benzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1NC1=CC=CC(Cl)=C1 GSDQYSSLIKJJOG-UHFFFAOYSA-N 0.000 description 1
• 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 description 1
• GDRVFDDBLLKWRI-UHFFFAOYSA-N 4H-quinolizine Chemical compound C1=CC=CN2CC=CC=C21 GDRVFDDBLLKWRI-UHFFFAOYSA-N 0.000 description 1
• IRPVABHDSJVBNZ-RTHVDDQRSA-N 5-[1-(cyclopropylmethyl)-5-[(1R,5S)-3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-6-yl]pyrazol-3-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C1=NN(CC2CC2)C(C2[C@@H]3CN(C[C@@H]32)C2COC2)=C1 IRPVABHDSJVBNZ-RTHVDDQRSA-N 0.000 description 1
• VKLKXFOZNHEBSW-UHFFFAOYSA-N 5-[[3-[(4-morpholin-4-ylbenzoyl)amino]phenyl]methoxy]pyridine-3-carboxamide Chemical compound O1CCN(CC1)C1=CC=C(C(=O)NC=2C=C(COC=3C=NC=C(C(=O)N)C=3)C=CC=2)C=C1 VKLKXFOZNHEBSW-UHFFFAOYSA-N 0.000 description 1
• XFJBGINZIMNZBW-CRAIPNDOSA-N 5-chloro-2-[4-[(1r,2s)-2-[2-(5-methylsulfonylpyridin-2-yl)oxyethyl]cyclopropyl]piperidin-1-yl]pyrimidine Chemical compound N1=CC(S(=O)(=O)C)=CC=C1OCC[C@H]1[C@@H](C2CCN(CC2)C=2N=CC(Cl)=CN=2)C1 XFJBGINZIMNZBW-CRAIPNDOSA-N 0.000 description 1
• SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 description 1
• IJRKLHTZAIFUTB-UHFFFAOYSA-N 5-nitro-2-(2-phenylethylamino)benzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC=C1NCCC1=CC=CC=C1 IJRKLHTZAIFUTB-UHFFFAOYSA-N 0.000 description 1
• XHLKOHSAWQPOFO-UHFFFAOYSA-N 5-phenyl-1h-imidazole Chemical compound N1C=NC=C1C1=CC=CC=C1 XHLKOHSAWQPOFO-UHFFFAOYSA-N 0.000 description 1
• AWBHWWVHNCWVBA-UHFFFAOYSA-N 6-(3,4-difluorophenyl)-2-[(3-methyl-1,2,4-oxadiazol-5-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CC1=NOC(CN2C(N3C=C(C=CC3=N2)C=2C=C(F)C(F)=CC=2)=O)=N1 AWBHWWVHNCWVBA-UHFFFAOYSA-N 0.000 description 1
• RSIWALKZYXPAGW-NSHDSACASA-N 6-(3-fluorophenyl)-3-methyl-7-[(1s)-1-(7h-purin-6-ylamino)ethyl]-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C=1([C@@H](NC=2C=3N=CNC=3N=CN=2)C)N=C2SC=C(C)N2C(=O)C=1C1=CC=CC(F)=C1 RSIWALKZYXPAGW-NSHDSACASA-N 0.000 description 1
• XVCKXUURUAEBQS-UHFFFAOYSA-N 6-(4-benzoylphenyl)-2-[(3-methyl-1,2,4-oxadiazol-5-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound CC1=NOC(CN2C(N3C=C(C=CC3=N2)C=2C=CC(=CC=2)C(=O)C=2C=CC=CC=2)=O)=N1 XVCKXUURUAEBQS-UHFFFAOYSA-N 0.000 description 1
• KCBWAFJCKVKYHO-UHFFFAOYSA-N 6-(4-cyclopropyl-6-methoxypyrimidin-5-yl)-1-[[4-[1-propan-2-yl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]pyrazolo[3,4-d]pyrimidine Chemical compound C1(CC1)C1=NC=NC(=C1C1=NC=C2C(=N1)N(N=C2)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C(C)C)OC KCBWAFJCKVKYHO-UHFFFAOYSA-N 0.000 description 1
• MEMWVMAOEBDEST-UHFFFAOYSA-N 6-[4-(4-fluorophenoxy)phenyl]-2-(2-pyrimidin-2-yloxyethyl)-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(F)=CC=C1OC1=CC=C(C2=CN3C(=O)N(CCOC=4N=CC=CN=4)N=C3C=C2)C=C1 MEMWVMAOEBDEST-UHFFFAOYSA-N 0.000 description 1
• COFSCJGADUHZIB-UHFFFAOYSA-N 6-[4-(trifluoromethoxy)phenyl]-2-[2-[3-(trifluoromethyl)pyridin-2-yl]oxyethyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCOC=3C(=CC=CN=3)C(F)(F)F)N=C2C=C1 COFSCJGADUHZIB-UHFFFAOYSA-N 0.000 description 1
• RAKKAYAIZQOSQT-UHFFFAOYSA-N 6-[4-(trifluoromethoxy)phenyl]-2-[2-[6-(trifluoromethyl)pyridin-2-yl]oxyethyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CN2C(=O)N(CCOC=3N=C(C=CC=3)C(F)(F)F)N=C2C=C1 RAKKAYAIZQOSQT-UHFFFAOYSA-N 0.000 description 1
• LNSFVRSSLQVLTP-UHFFFAOYSA-N 6-bromo-2-pyridin-2-yl-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound O=C1N2C=C(Br)C=CC2=NN1C1=CC=CC=N1 LNSFVRSSLQVLTP-UHFFFAOYSA-N 0.000 description 1
• SQJJGTRYJKBHNJ-UHFFFAOYSA-N 6-bromo-3-methyl-[1,2,4]triazolo[4,3-a]pyridine Chemical compound C1=CC(Br)=CN2C(C)=NN=C21 SQJJGTRYJKBHNJ-UHFFFAOYSA-N 0.000 description 1
• GDUANFXPOZTYKS-UHFFFAOYSA-N 6-bromo-8-[(2,6-difluoro-4-methoxybenzoyl)amino]-4-oxochromene-2-carboxylic acid Chemical compound FC1=CC(OC)=CC(F)=C1C(=O)NC1=CC(Br)=CC2=C1OC(C(O)=O)=CC2=O GDUANFXPOZTYKS-UHFFFAOYSA-N 0.000 description 1
• PFKZKSHKBBUZKU-UHFFFAOYSA-N 6-bromo-[1,2,4]triazolo[4,3-a]pyridine Chemical compound C1=C(Br)C=CC2=NN=CN21 PFKZKSHKBBUZKU-UHFFFAOYSA-N 0.000 description 1
• YZEOXYRILIORTM-UHFFFAOYSA-N 6-bromo-n-ethyl-[1,2,4]triazolo[4,3-a]pyridin-3-amine Chemical compound C1=CC(Br)=CN2C(NCC)=NN=C21 YZEOXYRILIORTM-UHFFFAOYSA-N 0.000 description 1
• HCCNBKFJYUWLEX-UHFFFAOYSA-N 7-(6-methoxypyridin-3-yl)-1-(2-propoxyethyl)-3-(pyrazin-2-ylmethylamino)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1NCC1=CN=CC=N1 HCCNBKFJYUWLEX-UHFFFAOYSA-N 0.000 description 1
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
• CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 1
• XASOHFCUIQARJT-UHFFFAOYSA-N 8-methoxy-6-[7-(2-morpholin-4-ylethoxy)imidazo[1,2-a]pyridin-3-yl]-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-one Chemical compound C(N1C(=O)C2=C(OC)C=C(C=3N4C(=NC=3)C=C(C=C4)OCCN3CCOCC3)C=C2CC1)C(F)(F)F XASOHFCUIQARJT-UHFFFAOYSA-N 0.000 description 1
• IRBAWVGZNJIROV-SFHVURJKSA-N 9-(2-cyclopropylethynyl)-2-[[(2s)-1,4-dioxan-2-yl]methoxy]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(C#CC4CC4)C=C3CCN2C(=O)N=C1OC[C@@H]1COCCO1 IRBAWVGZNJIROV-SFHVURJKSA-N 0.000 description 1
• 230000035502 ADME Effects 0.000 description 1
• RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
• 241000242759 Actiniaria Species 0.000 description 1
• JBMKAUGHUNFTOL-UHFFFAOYSA-N Aldoclor Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NC=NS2(=O)=O JBMKAUGHUNFTOL-UHFFFAOYSA-N 0.000 description 1
• 229940077274 Alpha glucosidase inhibitor Drugs 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
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
• 241000242762 Anemonia sulcata Species 0.000 description 1
• 208000019901 Anxiety disease Diseases 0.000 description 1
• 239000004475 Arginine Substances 0.000 description 1
• 241000168823 Asida Species 0.000 description 1
• 241000416162 Astragalus gummifer Species 0.000 description 1
• XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 description 1
• XUKUURHRXDUEBC-UHFFFAOYSA-N Atorvastatin Natural products C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CCC(O)CC(O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-UHFFFAOYSA-N 0.000 description 1
• 206010003662 Atrial flutter Diseases 0.000 description 1
• NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical group C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
• 239000005528 B01AC05 - Ticlopidine Substances 0.000 description 1
• IYHHRZBKXXKDDY-UHFFFAOYSA-N BI-605906 Chemical compound N=1C=2SC(C(N)=O)=C(N)C=2C(C(F)(F)CC)=CC=1N1CCC(S(C)(=O)=O)CC1 IYHHRZBKXXKDDY-UHFFFAOYSA-N 0.000 description 1
• 241000894006 Bacteria Species 0.000 description 1
• 239000005711 Benzoic acid Substances 0.000 description 1
• 229940123208 Biguanide Drugs 0.000 description 1
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
• 206010006458 Bronchitis chronic Diseases 0.000 description 1
• 239000002080 C09CA02 - Eprosartan Substances 0.000 description 1
• BGGALFIXXQOTPY-NRFANRHFSA-N C1(=C(C2=C(C=C1)N(C(C#N)=C2)C[C@@H](N1CCN(CC1)S(=O)(=O)C)C)C)CN1CCC(CC1)NC1=NC(=NC2=C1C=C(S2)CC(F)(F)F)NC Chemical compound C1(=C(C2=C(C=C1)N(C(C#N)=C2)C[C@@H](N1CCN(CC1)S(=O)(=O)C)C)C)CN1CCC(CC1)NC1=NC(=NC2=C1C=C(S2)CC(F)(F)F)NC BGGALFIXXQOTPY-NRFANRHFSA-N 0.000 description 1
• OJRUSAPKCPIVBY-KQYNXXCUSA-N C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N Chemical compound C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N OJRUSAPKCPIVBY-KQYNXXCUSA-N 0.000 description 1
• 125000006519 CCH3 Chemical group 0.000 description 1
• UHNRLQRZRNKOKU-UHFFFAOYSA-N CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O Chemical compound CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O UHNRLQRZRNKOKU-UHFFFAOYSA-N 0.000 description 1
• PKMUHQIDVVOXHQ-HXUWFJFHSA-N C[C@H](C1=CC(C2=CC=C(CNC3CCCC3)S2)=CC=C1)NC(C1=C(C)C=CC(NC2CNC2)=C1)=O Chemical compound C[C@H](C1=CC(C2=CC=C(CNC3CCCC3)S2)=CC=C1)NC(C1=C(C)C=CC(NC2CNC2)=C1)=O PKMUHQIDVVOXHQ-HXUWFJFHSA-N 0.000 description 1
• 101150085259 Cacna2d1 gene Proteins 0.000 description 1
• OYPRJOBELJOOCE-BKFZFHPZSA-N Calcium-45 Chemical compound [45Ca] OYPRJOBELJOOCE-BKFZFHPZSA-N 0.000 description 1
• PTHCMJGKKRQCBF-UHFFFAOYSA-N Cellulose, microcrystalline Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC)C(CO)O1 PTHCMJGKKRQCBF-UHFFFAOYSA-N 0.000 description 1
• 229930186147 Cephalosporin Natural products 0.000 description 1
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 1
• WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
• KPSRODZRAIWAKH-JTQLQIEISA-N Ciprofibrate Natural products C1=CC(OC(C)(C)C(O)=O)=CC=C1[C@H]1C(Cl)(Cl)C1 KPSRODZRAIWAKH-JTQLQIEISA-N 0.000 description 1
• 206010053567 Coagulopathies Diseases 0.000 description 1
• 108020004635 Complementary DNA Proteins 0.000 description 1
• 229940126657 Compound 17 Drugs 0.000 description 1
• 229940126639 Compound 33 Drugs 0.000 description 1
• 229920000742 Cotton Polymers 0.000 description 1
• TVZCRIROJQEVOT-CABCVRRESA-N Cromakalim Chemical compound N1([C@@H]2C3=CC(=CC=C3OC([C@H]2O)(C)C)C#N)CCCC1=O TVZCRIROJQEVOT-CABCVRRESA-N 0.000 description 1
• 108010069514 Cyclic Peptides Proteins 0.000 description 1
• 102000001189 Cyclic Peptides Human genes 0.000 description 1
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
• OJLOPKGSLYJEMD-LNQMSSPSSA-N Cyotec Chemical compound CCCCC(C)(O)CC=C[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)OC OJLOPKGSLYJEMD-LNQMSSPSSA-N 0.000 description 1
• FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
• FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
• RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
• KDXKERNSBIXSRK-RXMQYKEDSA-N D-lysine Chemical compound NCCCC[C@@H](N)C(O)=O KDXKERNSBIXSRK-RXMQYKEDSA-N 0.000 description 1
• 108020004414 DNA Proteins 0.000 description 1
• 208000020401 Depressive disease Diseases 0.000 description 1
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
• 206010052337 Diastolic dysfunction Diseases 0.000 description 1
• 240000001879 Digitalis lutea Species 0.000 description 1
• WDJUZGPOPHTGOT-OAXVISGBSA-N Digitoxin Natural products O([C@H]1[C@@H](C)O[C@@H](O[C@@H]2C[C@@H]3[C@@](C)([C@@H]4[C@H]([C@]5(O)[C@@](C)([C@H](C6=CC(=O)OC6)CC5)CC4)CC3)CC2)C[C@H]1O)[C@H]1O[C@@H](C)[C@H](O[C@H]2O[C@@H](C)[C@@H](O)[C@@H](O)C2)[C@@H](O)C1 WDJUZGPOPHTGOT-OAXVISGBSA-N 0.000 description 1
• LTMHDMANZUZIPE-AMTYYWEZSA-N Digoxin Natural products O([C@H]1[C@H](C)O[C@H](O[C@@H]2C[C@@H]3[C@@](C)([C@@H]4[C@H]([C@]5(O)[C@](C)([C@H](O)C4)[C@H](C4=CC(=O)OC4)CC5)CC3)CC2)C[C@@H]1O)[C@H]1O[C@H](C)[C@@H](O[C@H]2O[C@@H](C)[C@H](O)[C@@H](O)C2)[C@@H](O)C1 LTMHDMANZUZIPE-AMTYYWEZSA-N 0.000 description 1
• 201000007547 Dravet syndrome Diseases 0.000 description 1
• 208000032928 Dyslipidaemia Diseases 0.000 description 1
• 206010014486 Elevated triglycerides Diseases 0.000 description 1
• 206010014561 Emphysema Diseases 0.000 description 1
• BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
• 239000005977 Ethylene Substances 0.000 description 1
• IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
• PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
• 229920003134 Eudragit® polymer Polymers 0.000 description 1
• GISRWBROCYNDME-PELMWDNLSA-N F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C Chemical compound F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C GISRWBROCYNDME-PELMWDNLSA-N 0.000 description 1
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
• 241000233866 Fungi Species 0.000 description 1
• 229940126656 GS-4224 Drugs 0.000 description 1
• 208000007882 Gastritis Diseases 0.000 description 1
• 208000005577 Gastroenteritis Diseases 0.000 description 1
• CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical compound O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 0.000 description 1
• 229930182566 Gentamicin Natural products 0.000 description 1
• RGHNJXZEOKUKBD-SQOUGZDYSA-N Gluconic acid Natural products OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 1
• 208000002705 Glucose Intolerance Diseases 0.000 description 1
• 206010018429 Glucose tolerance impaired Diseases 0.000 description 1
• JMBQKKAJIKAWKF-UHFFFAOYSA-N Glutethimide Chemical compound C=1C=CC=CC=1C1(CC)CCC(=O)NC1=O JMBQKKAJIKAWKF-UHFFFAOYSA-N 0.000 description 1
• 102000003886 Glycoproteins Human genes 0.000 description 1
• 108090000288 Glycoproteins Proteins 0.000 description 1
• 229920000084 Gum arabic Polymers 0.000 description 1
• 229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 1
• 108010081348 HRT1 protein Hairy Proteins 0.000 description 1
• 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 description 1
• HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 1
• 229940122957 Histamine H2 receptor antagonist Drugs 0.000 description 1
• 101100058867 Homo sapiens CACNA1C gene Proteins 0.000 description 1
• 101100382226 Homo sapiens CACNB2 gene Proteins 0.000 description 1
• 101001047090 Homo sapiens Potassium voltage-gated channel subfamily H member 2 Proteins 0.000 description 1
• 101000694017 Homo sapiens Sodium channel protein type 5 subunit alpha Proteins 0.000 description 1
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
• 102000004877 Insulin Human genes 0.000 description 1
• 108090001061 Insulin Proteins 0.000 description 1
• 206010022489 Insulin Resistance 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
• 229930194542 Keto Natural products 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
• CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
• ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
• 229930182816 L-glutamine Natural products 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
• 241000218652 Larix Species 0.000 description 1
• 235000005590 Larix decidua Nutrition 0.000 description 1
• NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 1
• 208000017170 Lipid metabolism disease Diseases 0.000 description 1
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
• KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
• 239000004472 Lysine Substances 0.000 description 1
• NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 description 1
• 208000001145 Metabolic Syndrome Diseases 0.000 description 1
• CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
• FQISKWAFAHGMGT-SGJOWKDISA-M Methylprednisolone sodium succinate Chemical compound [Na+].C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)[C@@](O)(C(=O)COC(=O)CCC([O-])=O)CC[C@H]21 FQISKWAFAHGMGT-SGJOWKDISA-M 0.000 description 1
• 208000019695 Migraine disease Diseases 0.000 description 1
• 108010052185 Myotonin-Protein Kinase Proteins 0.000 description 1
• 102100022437 Myotonin-protein kinase Human genes 0.000 description 1
• 235000009421 Myristica fragrans Nutrition 0.000 description 1
• AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 1
• LVDRREOUMKACNJ-BKMJKUGQSA-N N-[(2R,3S)-2-(4-chlorophenyl)-1-(1,4-dimethyl-2-oxoquinolin-7-yl)-6-oxopiperidin-3-yl]-2-methylpropane-1-sulfonamide Chemical compound CC(C)CS(=O)(=O)N[C@H]1CCC(=O)N([C@@H]1c1ccc(Cl)cc1)c1ccc2c(C)cc(=O)n(C)c2c1 LVDRREOUMKACNJ-BKMJKUGQSA-N 0.000 description 1
• LIMFPAAAIVQRRD-BCGVJQADSA-N N-[2-[(3S,4R)-3-fluoro-4-methoxypiperidin-1-yl]pyrimidin-4-yl]-8-[(2R,3S)-2-methyl-3-(methylsulfonylmethyl)azetidin-1-yl]-5-propan-2-ylisoquinolin-3-amine Chemical compound F[C@H]1CN(CC[C@H]1OC)C1=NC=CC(=N1)NC=1N=CC2=C(C=CC(=C2C=1)C(C)C)N1[C@@H]([C@H](C1)CS(=O)(=O)C)C LIMFPAAAIVQRRD-BCGVJQADSA-N 0.000 description 1
• AVYVHIKSFXVDBG-UHFFFAOYSA-N N-benzyl-N-hydroxy-2,2-dimethylbutanamide Chemical compound C(C1=CC=CC=C1)N(C(C(CC)(C)C)=O)O AVYVHIKSFXVDBG-UHFFFAOYSA-N 0.000 description 1
• POFVJRKJJBFPII-UHFFFAOYSA-N N-cyclopentyl-5-[2-[[5-[(4-ethylpiperazin-1-yl)methyl]pyridin-2-yl]amino]-5-fluoropyrimidin-4-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound C1(CCCC1)NC=1SC(=C(N=1)C)C1=NC(=NC=C1F)NC1=NC=C(C=C1)CN1CCN(CC1)CC POFVJRKJJBFPII-UHFFFAOYSA-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
• OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 1
• 229910002651 NO3 Inorganic materials 0.000 description 1
• 229910003813 NRa Inorganic materials 0.000 description 1
• ZBBHBTPTTSWHBA-UHFFFAOYSA-N Nicardipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCN(C)CC=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 ZBBHBTPTTSWHBA-UHFFFAOYSA-N 0.000 description 1
• NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
• SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 description 1
• 239000000006 Nitroglycerin Substances 0.000 description 1
• WXOMTJVVIMOXJL-BOBFKVMVSA-A O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O[Al](O)O.O[Al](O)O.O[Al](O)O.O[Al](O)O.O[Al](O)O.O[Al](O)O.O[Al](O)O.O[Al](O)O.O[Al](O)OS(=O)(=O)OC[C@H]1O[C@@H](O[C@]2(COS(=O)(=O)O[Al](O)O)O[C@H](OS(=O)(=O)O[Al](O)O)[C@@H](OS(=O)(=O)O[Al](O)O)[C@@H]2OS(=O)(=O)O[Al](O)O)[C@H](OS(=O)(=O)O[Al](O)O)[C@@H](OS(=O)(=O)O[Al](O)O)[C@@H]1OS(=O)(=O)O[Al](O)O Chemical compound O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O[Al](O)O.O[Al](O)O.O[Al](O)O.O[Al](O)O.O[Al](O)O.O[Al](O)O.O[Al](O)O.O[Al](O)O.O[Al](O)OS(=O)(=O)OC[C@H]1O[C@@H](O[C@]2(COS(=O)(=O)O[Al](O)O)O[C@H](OS(=O)(=O)O[Al](O)O)[C@@H](OS(=O)(=O)O[Al](O)O)[C@@H]2OS(=O)(=O)O[Al](O)O)[C@H](OS(=O)(=O)O[Al](O)O)[C@@H](OS(=O)(=O)O[Al](O)O)[C@@H]1OS(=O)(=O)O[Al](O)O WXOMTJVVIMOXJL-BOBFKVMVSA-A 0.000 description 1
• IDRGFNPZDVBSSE-UHFFFAOYSA-N OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F Chemical compound OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F IDRGFNPZDVBSSE-UHFFFAOYSA-N 0.000 description 1
• 208000008589 Obesity Diseases 0.000 description 1
• 206010033645 Pancreatitis Diseases 0.000 description 1
• IQPSEEYGBUAQFF-UHFFFAOYSA-N Pantoprazole Chemical compound COC1=CC=NC(CS(=O)C=2NC3=CC=C(OC(F)F)C=C3N=2)=C1OC IQPSEEYGBUAQFF-UHFFFAOYSA-N 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
• JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
• 208000008469 Peptic Ulcer Diseases 0.000 description 1
• 239000004698 Polyethylene Substances 0.000 description 1
• 239000002202 Polyethylene glycol Substances 0.000 description 1
• 108010040201 Polymyxins Proteins 0.000 description 1
• 229920001214 Polysorbate 60 Polymers 0.000 description 1
• 102100022807 Potassium voltage-gated channel subfamily H member 2 Human genes 0.000 description 1
• TUZYXOIXSAXUGO-UHFFFAOYSA-N Pravastatin Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(O)C=C21 TUZYXOIXSAXUGO-UHFFFAOYSA-N 0.000 description 1
• 208000008376 Pre-Excitation Syndromes Diseases 0.000 description 1
• 206010064911 Pulmonary arterial hypertension Diseases 0.000 description 1
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
• IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
• 241000700159 Rattus Species 0.000 description 1
• 206010058156 Reperfusion arrhythmia Diseases 0.000 description 1
• LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
• QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 1
• 241000220010 Rhode Species 0.000 description 1
• AJLFOPYRIVGYMJ-UHFFFAOYSA-N SJ000287055 Natural products C12C(OC(=O)C(C)CC)CCC=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 AJLFOPYRIVGYMJ-UHFFFAOYSA-N 0.000 description 1
• XTZNCVSCVHTPAI-UHFFFAOYSA-N Salmeterol xinafoate Chemical compound C1=CC=CC2=C(O)C(C(=O)O)=CC=C21.C1=C(O)C(CO)=CC(C(O)CNCCCCCCOCCCCC=2C=CC=CC=2)=C1 XTZNCVSCVHTPAI-UHFFFAOYSA-N 0.000 description 1
• 229940124639 Selective inhibitor Drugs 0.000 description 1
• 229920001800 Shellac Polymers 0.000 description 1
• PNUZDKCDAWUEGK-CYZMBNFOSA-N Sitafloxacin Chemical compound C([C@H]1N)N(C=2C(=C3C(C(C(C(O)=O)=CN3[C@H]3[C@H](C3)F)=O)=CC=2F)Cl)CC11CC1 PNUZDKCDAWUEGK-CYZMBNFOSA-N 0.000 description 1
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
• 102100027198 Sodium channel protein type 5 subunit alpha Human genes 0.000 description 1
• HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 1
• 235000021355 Stearic acid Nutrition 0.000 description 1
• 108010034396 Streptogramins Proteins 0.000 description 1
• 108010023197 Streptokinase Proteins 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Chemical class OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
• NHUHCSRWZMLRLA-UHFFFAOYSA-N Sulfisoxazole Chemical compound CC1=NOC(NS(=O)(=O)C=2C=CC(N)=CC=2)=C1C NHUHCSRWZMLRLA-UHFFFAOYSA-N 0.000 description 1
• 229940100389 Sulfonylurea Drugs 0.000 description 1
• 208000003734 Supraventricular 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
• 239000005939 Tefluthrin Substances 0.000 description 1
• 108010039185 Tenecteplase Proteins 0.000 description 1
• DQHNAVOVODVIMG-UHFFFAOYSA-M Tiotropium bromide Chemical compound [Br-].C1C(C2C3O2)[N+](C)(C)C3CC1OC(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 DQHNAVOVODVIMG-UHFFFAOYSA-M 0.000 description 1
• 229920001615 Tragacanth Polymers 0.000 description 1
• YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
• 102000004142 Trypsin Human genes 0.000 description 1
• 108090000631 Trypsin Proteins 0.000 description 1
• 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 1
• 108090000435 Urokinase-type plasminogen activator Proteins 0.000 description 1
• 102000003990 Urokinase-type plasminogen activator Human genes 0.000 description 1
• 108010059993 Vancomycin Proteins 0.000 description 1
• FVECELJHCSPHKY-UHFFFAOYSA-N Veratridine Natural products C1=C(OC)C(OC)=CC=C1C(=O)OC1C2(O)OC34CC5(O)C(CN6C(CCC(C)C6)C6(C)O)C6(O)C(O)CC5(O)C4CCC2C3(C)CC1 FVECELJHCSPHKY-UHFFFAOYSA-N 0.000 description 1
• LXRZVMYMQHNYJB-UNXOBOICSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 LXRZVMYMQHNYJB-UNXOBOICSA-N 0.000 description 1
• SPXSEZMVRJLHQG-XMMPIXPASA-N [(2R)-1-[[4-[(3-phenylmethoxyphenoxy)methyl]phenyl]methyl]pyrrolidin-2-yl]methanol Chemical compound C(C1=CC=CC=C1)OC=1C=C(OCC2=CC=C(CN3[C@H](CCC3)CO)C=C2)C=CC=1 SPXSEZMVRJLHQG-XMMPIXPASA-N 0.000 description 1
• IOSLINNLJFQMFF-XMMPIXPASA-N [(2R)-1-[[4-[[3-[(4-fluorophenyl)methylsulfanyl]phenoxy]methyl]phenyl]methyl]pyrrolidin-2-yl]methanol Chemical compound FC1=CC=C(CSC=2C=C(OCC3=CC=C(CN4[C@H](CCC4)CO)C=C3)C=CC=2)C=C1 IOSLINNLJFQMFF-XMMPIXPASA-N 0.000 description 1
• LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 1
• DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
• 229960000446 abciximab Drugs 0.000 description 1
• 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 description 1
• 238000010521 absorption reaction Methods 0.000 description 1
• 235000010489 acacia gum Nutrition 0.000 description 1
• 239000000205 acacia gum Substances 0.000 description 1
• 229940077422 accupril Drugs 0.000 description 1
• 229960002122 acebutolol Drugs 0.000 description 1
• 229940081735 acetylcellulose Drugs 0.000 description 1
• 230000002378 acidificating effect Effects 0.000 description 1
• 239000011149 active material Substances 0.000 description 1
• 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
• 229960001456 adenosine triphosphate Drugs 0.000 description 1
• 239000002671 adjuvant Substances 0.000 description 1
• 239000000674 adrenergic antagonist Substances 0.000 description 1
• 210000002934 adrenergic neuron Anatomy 0.000 description 1
• 239000000443 aerosol Substances 0.000 description 1
• 150000001298 alcohols Chemical class 0.000 description 1
• 229940092229 aldactone Drugs 0.000 description 1
• 150000001299 aldehydes Chemical class 0.000 description 1
• QBYJBZPUGVGKQQ-SJJAEHHWSA-N aldrin Chemical compound C1[C@H]2C=C[C@@H]1[C@H]1[C@@](C3(Cl)Cl)(Cl)C(Cl)=C(Cl)[C@@]3(Cl)[C@H]12 QBYJBZPUGVGKQQ-SJJAEHHWSA-N 0.000 description 1
• 235000010443 alginic acid Nutrition 0.000 description 1
• 229920000615 alginic acid Polymers 0.000 description 1
• 229910052783 alkali metal Inorganic materials 0.000 description 1
• 150000001340 alkali metals Chemical class 0.000 description 1
• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
• 125000002877 alkyl aryl group Chemical group 0.000 description 1
• 125000005907 alkyl ester group Chemical group 0.000 description 1
• 125000005377 alkyl thioxy group Chemical group 0.000 description 1
• 230000029936 alkylation Effects 0.000 description 1
• 238000005804 alkylation reaction Methods 0.000 description 1
• 239000002160 alpha blocker Substances 0.000 description 1
• 239000003888 alpha glucosidase inhibitor Substances 0.000 description 1
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
• 102000015007 alpha-adrenergic receptor activity proteins Human genes 0.000 description 1
• 108040006816 alpha-adrenergic receptor activity proteins Proteins 0.000 description 1
• BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Chemical class OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
• 229960004821 amikacin Drugs 0.000 description 1
• LKCWBDHBTVXHDL-RMDFUYIESA-N amikacin Chemical compound O([C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O[C@@H]1[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O1)O)NC(=O)[C@@H](O)CCN)[C@H]1O[C@H](CN)[C@@H](O)[C@H](O)[C@H]1O LKCWBDHBTVXHDL-RMDFUYIESA-N 0.000 description 1
• 229940024606 amino acid Drugs 0.000 description 1
• 150000001413 amino acids Chemical class 0.000 description 1
• 229940126575 aminoglycoside Drugs 0.000 description 1
• 229960000836 amitriptyline Drugs 0.000 description 1
• 229960000528 amlodipine Drugs 0.000 description 1
• LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 description 1
• 229960003022 amoxicillin Drugs 0.000 description 1
• 229940003354 angiomax Drugs 0.000 description 1
• 239000002333 angiotensin II receptor antagonist Substances 0.000 description 1
• 229950006323 angiotensin ii Drugs 0.000 description 1
• 230000002547 anomalous effect Effects 0.000 description 1
• 229940069428 antacid Drugs 0.000 description 1
• 239000003159 antacid agent Substances 0.000 description 1
• 230000001078 anti-cholinergic effect Effects 0.000 description 1
• 229950005617 aprikalim Drugs 0.000 description 1
• 239000003125 aqueous solvent Substances 0.000 description 1
• KXNPVXPOPUZYGB-XYVMCAHJSA-N argatroban Chemical compound OC(=O)[C@H]1C[C@H](C)CCN1C(=O)[C@H](CCCN=C(N)N)NS(=O)(=O)C1=CC=CC2=C1NC[C@H](C)C2 KXNPVXPOPUZYGB-XYVMCAHJSA-N 0.000 description 1
• 229960003856 argatroban 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
• 210000000617 arm Anatomy 0.000 description 1
• 150000004982 aromatic amines Chemical class 0.000 description 1
• 229940009098 aspartate Drugs 0.000 description 1
• 208000006673 asthma Diseases 0.000 description 1
• XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 description 1
• METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 description 1
• 229960002274 atenolol Drugs 0.000 description 1
• 229960005370 atorvastatin Drugs 0.000 description 1
• SHZPNDRIDUBNMH-NIJVSVLQSA-L atorvastatin calcium trihydrate Chemical compound O.O.O.[Ca+2].C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC([O-])=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1.C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC([O-])=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 SHZPNDRIDUBNMH-NIJVSVLQSA-L 0.000 description 1
• 206010003668 atrial tachycardia Diseases 0.000 description 1
• 210000001992 atrioventricular node Anatomy 0.000 description 1
• 229940098165 atrovent Drugs 0.000 description 1
• 229940072293 axid Drugs 0.000 description 1
• YEESUBCSWGVPCE-UHFFFAOYSA-N azanylidyneoxidanium iron(2+) pentacyanide Chemical compound [Fe++].[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.N#[O+] YEESUBCSWGVPCE-UHFFFAOYSA-N 0.000 description 1
• 229940125717 barbiturate Drugs 0.000 description 1
• 229960004530 benazepril Drugs 0.000 description 1
• 229940049706 benzodiazepine Drugs 0.000 description 1
• 150000001557 benzodiazepines Chemical class 0.000 description 1
• 235000010233 benzoic acid Nutrition 0.000 description 1
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
• 229960003665 bepridil Drugs 0.000 description 1
• 239000003782 beta lactam antibiotic agent Substances 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
• 229960003237 betaine Drugs 0.000 description 1
• 229960004324 betaxolol Drugs 0.000 description 1
• 150000004283 biguanides Chemical class 0.000 description 1
• 229950005453 bimakalim Drugs 0.000 description 1
• 239000011230 binding agent Substances 0.000 description 1
• 239000004305 biphenyl Substances 0.000 description 1
• 235000010290 biphenyl Nutrition 0.000 description 1
• VHYCDWMUTMEGQY-UHFFFAOYSA-N bisoprolol Chemical compound CC(C)NCC(O)COC1=CC=C(COCCOC(C)C)C=C1 VHYCDWMUTMEGQY-UHFFFAOYSA-N 0.000 description 1
• 229960002781 bisoprolol Drugs 0.000 description 1
• 229940043064 bisoprolol / hydrochlorothiazide Drugs 0.000 description 1
• VMDFASMUILANOL-WXXKFALUSA-N bisoprolol fumarate Chemical compound [H+].[H+].[O-]C(=O)\C=C\C([O-])=O.CC(C)NCC(O)COC1=CC=C(COCCOC(C)C)C=C1.CC(C)NCC(O)COC1=CC=C(COCCOC(C)C)C=C1 VMDFASMUILANOL-WXXKFALUSA-N 0.000 description 1
• 229960001500 bivalirudin Drugs 0.000 description 1
• 239000002981 blocking agent Substances 0.000 description 1
• 230000008499 blood brain barrier function Effects 0.000 description 1
• 230000023555 blood coagulation Effects 0.000 description 1
• 210000001218 blood-brain barrier Anatomy 0.000 description 1
• 208000006218 bradycardia Diseases 0.000 description 1
• 210000005013 brain tissue Anatomy 0.000 description 1
• 229940097683 brevibloc Drugs 0.000 description 1
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
• 229910052794 bromium Inorganic materials 0.000 description 1
• 206010006451 bronchitis Diseases 0.000 description 1
• 229940124630 bronchodilator Drugs 0.000 description 1
• 239000000168 bronchodilator agent Substances 0.000 description 1
• 229960004064 bumetanide Drugs 0.000 description 1
• 229940088498 bumex Drugs 0.000 description 1
• 229960001058 bupropion Drugs 0.000 description 1
• KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical class O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
• 229910000024 caesium carbonate Inorganic materials 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
• 239000001506 calcium phosphate Substances 0.000 description 1
• 229910000389 calcium phosphate Inorganic materials 0.000 description 1
• 235000011010 calcium phosphates Nutrition 0.000 description 1
• 239000000378 calcium silicate Substances 0.000 description 1
• 229910052918 calcium silicate Inorganic materials 0.000 description 1
• 229960003340 calcium silicate Drugs 0.000 description 1
• 235000012241 calcium silicate Nutrition 0.000 description 1
• OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
• HTQMVQVXFRQIKW-UHFFFAOYSA-N candesartan Chemical compound CCOC1=NC2=CC=CC(C(O)=O)=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C1=NN=NN1 HTQMVQVXFRQIKW-UHFFFAOYSA-N 0.000 description 1
• 125000002837 carbocyclic group Chemical group 0.000 description 1
• 150000001722 carbon compounds Chemical class 0.000 description 1
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
• 229940072282 cardura Drugs 0.000 description 1
• 239000000969 carrier Substances 0.000 description 1
• 229960001222 carteolol Drugs 0.000 description 1
• 229960004195 carvedilol Drugs 0.000 description 1
• 125000002091 cationic group Chemical group 0.000 description 1
• 150000001768 cations Chemical class 0.000 description 1
• 229940097644 cedax Drugs 0.000 description 1
• 229960004841 cefadroxil Drugs 0.000 description 1
• NBFNMSULHIODTC-CYJZLJNKSA-N cefadroxil monohydrate Chemical compound O.C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CC=C(O)C=C1 NBFNMSULHIODTC-CYJZLJNKSA-N 0.000 description 1
• MLYYVTUWGNIJIB-BXKDBHETSA-N cefazolin Chemical compound S1C(C)=NN=C1SCC1=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CN3N=NN=C3)[C@H]2SC1 MLYYVTUWGNIJIB-BXKDBHETSA-N 0.000 description 1
• 229960001139 cefazolin Drugs 0.000 description 1
• RTXOFQZKPXMALH-GHXIOONMSA-N cefdinir Chemical compound S1C(N)=NC(C(=N\O)\C(=O)N[C@@H]2C(N3C(=C(C=C)CS[C@@H]32)C(O)=O)=O)=C1 RTXOFQZKPXMALH-GHXIOONMSA-N 0.000 description 1
• 229960002129 cefixime Drugs 0.000 description 1
• 229960004797 cefpodoxime proxetil Drugs 0.000 description 1
• 229960002580 cefprozil Drugs 0.000 description 1
• 229960002588 cefradine Drugs 0.000 description 1
• 229940047496 ceftin Drugs 0.000 description 1
• VAAUVRVFOQPIGI-SPQHTLEESA-N ceftriaxone Chemical compound S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1CSC1=NC(=O)C(=O)NN1C VAAUVRVFOQPIGI-SPQHTLEESA-N 0.000 description 1
• 229960004755 ceftriaxone Drugs 0.000 description 1
• 229940099237 cefzil Drugs 0.000 description 1
• 229940047493 celexa Drugs 0.000 description 1
• 238000004113 cell culture Methods 0.000 description 1
• 229920002301 cellulose acetate Polymers 0.000 description 1
• 210000003169 central nervous system Anatomy 0.000 description 1
• 229940083181 centrally acting adntiadrenergic agent methyldopa Drugs 0.000 description 1
• 229940106164 cephalexin Drugs 0.000 description 1
• 229940124587 cephalosporin Drugs 0.000 description 1
• 150000001780 cephalosporins Chemical class 0.000 description 1
• 229960000541 cetyl alcohol Drugs 0.000 description 1
• KEWHKYJURDBRMN-XSAPEOHZSA-M chembl2134724 Chemical compound O.[Br-].O([C@H]1C[C@H]2CC[C@@H](C1)[N+]2(C)C(C)C)C(=O)C(CO)C1=CC=CC=C1 KEWHKYJURDBRMN-XSAPEOHZSA-M 0.000 description 1
• 125000003636 chemical group Chemical group 0.000 description 1
• 238000010568 chiral column chromatography Methods 0.000 description 1
• RNFNDJAIBTYOQL-UHFFFAOYSA-N chloral hydrate Chemical compound OC(O)C(Cl)(Cl)Cl RNFNDJAIBTYOQL-UHFFFAOYSA-N 0.000 description 1
• 229960002327 chloral hydrate Drugs 0.000 description 1
• 229960004926 chlorobutanol Drugs 0.000 description 1
• 229960001523 chlortalidone Drugs 0.000 description 1
• 235000012000 cholesterol Nutrition 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
• VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 description 1
• 208000007451 chronic bronchitis Diseases 0.000 description 1
• 230000001684 chronic effect Effects 0.000 description 1
• RRGUKTPIGVIEKM-UHFFFAOYSA-N cilostazol Chemical compound C=1C=C2NC(=O)CCC2=CC=1OCCCCC1=NN=NN1C1CCCCC1 RRGUKTPIGVIEKM-UHFFFAOYSA-N 0.000 description 1
• 229960004588 cilostazol Drugs 0.000 description 1
• AQIXAKUUQRKLND-UHFFFAOYSA-N cimetidine Chemical compound N#C/N=C(/NC)NCCSCC=1N=CNC=1C AQIXAKUUQRKLND-UHFFFAOYSA-N 0.000 description 1
• LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
• 235000013985 cinnamic acid Nutrition 0.000 description 1
• 229930016911 cinnamic acid Natural products 0.000 description 1
• 229960002174 ciprofibrate Drugs 0.000 description 1
• 229960003405 ciprofloxacin Drugs 0.000 description 1
• 230000004087 circulation Effects 0.000 description 1
• DCSUBABJRXZOMT-IRLDBZIGSA-N cisapride Chemical compound C([C@@H]([C@@H](CC1)NC(=O)C=2C(=CC(N)=C(Cl)C=2)OC)OC)N1CCCOC1=CC=C(F)C=C1 DCSUBABJRXZOMT-IRLDBZIGSA-N 0.000 description 1
• 229960005132 cisapride Drugs 0.000 description 1
• DCSUBABJRXZOMT-UHFFFAOYSA-N cisapride Natural products C1CC(NC(=O)C=2C(=CC(N)=C(Cl)C=2)OC)C(OC)CN1CCCOC1=CC=C(F)C=C1 DCSUBABJRXZOMT-UHFFFAOYSA-N 0.000 description 1
• 229960001653 citalopram Drugs 0.000 description 1
• 235000015165 citric acid Nutrition 0.000 description 1
• 208000024980 claudication Diseases 0.000 description 1
• 230000009194 climbing Effects 0.000 description 1
• 229960002227 clindamycin Drugs 0.000 description 1
• KDLRVYVGXIQJDK-AWPVFWJPSA-N clindamycin Chemical compound CN1C[C@H](CCC)C[C@H]1C(=O)N[C@H]([C@H](C)Cl)[C@@H]1[C@H](O)[C@H](O)[C@@H](O)[C@@H](SC)O1 KDLRVYVGXIQJDK-AWPVFWJPSA-N 0.000 description 1
• FDEODCTUSIWGLK-RSAXXLAASA-N clopidogrel sulfate Chemical compound [H+].OS([O-])(=O)=O.C1([C@H](N2CC=3C=CSC=3CC2)C(=O)OC)=CC=CC=C1Cl FDEODCTUSIWGLK-RSAXXLAASA-N 0.000 description 1
• 229940070395 clorpres Drugs 0.000 description 1
• 239000011248 coating agent Substances 0.000 description 1
• 229940075614 colloidal silicon dioxide Drugs 0.000 description 1
• 239000003086 colorant Substances 0.000 description 1
• 238000002648 combination therapy Methods 0.000 description 1
• 229940110933 combipres Drugs 0.000 description 1
• 239000002131 composite material Substances 0.000 description 1
• 229940125904 compound 1 Drugs 0.000 description 1
• 229940125797 compound 12 Drugs 0.000 description 1
• 229940126543 compound 14 Drugs 0.000 description 1
• 229940125758 compound 15 Drugs 0.000 description 1
• 229940126142 compound 16 Drugs 0.000 description 1
• 229940125782 compound 2 Drugs 0.000 description 1
• 229940126086 compound 21 Drugs 0.000 description 1
• 229940126208 compound 22 Drugs 0.000 description 1
• 229940125961 compound 24 Drugs 0.000 description 1
• 229940125846 compound 25 Drugs 0.000 description 1
• 229940125851 compound 27 Drugs 0.000 description 1
• 229940126214 compound 3 Drugs 0.000 description 1
• 229940125877 compound 31 Drugs 0.000 description 1
• 229940125878 compound 36 Drugs 0.000 description 1
• 229940125807 compound 37 Drugs 0.000 description 1
• 229940127573 compound 38 Drugs 0.000 description 1
• 229940126540 compound 41 Drugs 0.000 description 1
• 229940125936 compound 42 Drugs 0.000 description 1
• 229940125844 compound 46 Drugs 0.000 description 1
• 229940127271 compound 49 Drugs 0.000 description 1
• 229940125898 compound 5 Drugs 0.000 description 1
• 229940126545 compound 53 Drugs 0.000 description 1
• 229940125900 compound 59 Drugs 0.000 description 1
• 229940126179 compound 72 Drugs 0.000 description 1
• 238000007906 compression Methods 0.000 description 1
• 230000006835 compression Effects 0.000 description 1
• 238000010276 construction Methods 0.000 description 1
• 230000009091 contractile dysfunction Effects 0.000 description 1
• 230000008602 contraction Effects 0.000 description 1
• 238000007796 conventional method Methods 0.000 description 1
• 229940069210 coreg Drugs 0.000 description 1
• 208000029078 coronary artery disease Diseases 0.000 description 1
• 239000003246 corticosteroid Substances 0.000 description 1
• 229960001334 corticosteroids Drugs 0.000 description 1
• 235000012343 cottonseed oil Nutrition 0.000 description 1
• 239000002385 cottonseed oil Substances 0.000 description 1
• 229940072645 coumadin Drugs 0.000 description 1
• 229940111134 coxibs Drugs 0.000 description 1
• 229940097499 cozaar Drugs 0.000 description 1
• 229940066901 crestor Drugs 0.000 description 1
• 229950004210 cromakalim Drugs 0.000 description 1
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
• 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 description 1
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
• 229940099378 cytotec Drugs 0.000 description 1
• 229960003828 danaparoid Drugs 0.000 description 1
• 230000003111 delayed effect Effects 0.000 description 1
• 238000001514 detection method Methods 0.000 description 1
• 125000005266 diarylamine group Chemical group 0.000 description 1
• 230000003205 diastolic effect Effects 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
• 208000010643 digestive system disease Diseases 0.000 description 1
• WDJUZGPOPHTGOT-XUDUSOBPSA-N digitoxin Chemical compound C1[C@H](O)[C@H](O)[C@@H](C)O[C@H]1O[C@@H]1[C@@H](C)O[C@@H](O[C@@H]2[C@H](O[C@@H](O[C@@H]3C[C@@H]4[C@]([C@@H]5[C@H]([C@]6(CC[C@@H]([C@@]6(C)CC5)C=5COC(=O)C=5)O)CC4)(C)CC3)C[C@@H]2O)C)C[C@@H]1O WDJUZGPOPHTGOT-XUDUSOBPSA-N 0.000 description 1
• 229960000648 digitoxin Drugs 0.000 description 1
• GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
• LTMHDMANZUZIPE-PUGKRICDSA-N digoxin Chemical compound C1[C@H](O)[C@H](O)[C@@H](C)O[C@H]1O[C@@H]1[C@@H](C)O[C@@H](O[C@@H]2[C@H](O[C@@H](O[C@@H]3C[C@@H]4[C@]([C@@H]5[C@H]([C@]6(CC[C@@H]([C@@]6(C)[C@H](O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)C[C@@H]2O)C)C[C@@H]1O LTMHDMANZUZIPE-PUGKRICDSA-N 0.000 description 1
• 229960005156 digoxin Drugs 0.000 description 1
• LTMHDMANZUZIPE-UHFFFAOYSA-N digoxine Natural products C1C(O)C(O)C(C)OC1OC1C(C)OC(OC2C(OC(OC3CC4C(C5C(C6(CCC(C6(C)C(O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)CC2O)C)CC1O LTMHDMANZUZIPE-UHFFFAOYSA-N 0.000 description 1
• 238000007865 diluting Methods 0.000 description 1
• UXGNZZKBCMGWAZ-UHFFFAOYSA-N dimethylformamide dmf Chemical compound CN(C)C=O.CN(C)C=O UXGNZZKBCMGWAZ-UHFFFAOYSA-N 0.000 description 1
• 229910001873 dinitrogen Inorganic materials 0.000 description 1
• 230000008034 disappearance Effects 0.000 description 1
• CETRZFQIITUQQL-UHFFFAOYSA-N dmso dimethylsulfoxide Chemical compound CS(C)=O.CS(C)=O CETRZFQIITUQQL-UHFFFAOYSA-N 0.000 description 1
• 229960000220 doxazosin mesylate Drugs 0.000 description 1
• 239000013583 drug formulation Substances 0.000 description 1
• 210000001198 duodenum Anatomy 0.000 description 1
• 229940099739 duricef Drugs 0.000 description 1
• 229940011681 elavil Drugs 0.000 description 1
• 239000003792 electrolyte Substances 0.000 description 1
• 229950003424 emakalim Drugs 0.000 description 1
• 239000003995 emulsifying agent Substances 0.000 description 1
• 230000001804 emulsifying effect Effects 0.000 description 1
• 108010048367 enhanced green fluorescent protein Proteins 0.000 description 1
• 239000003623 enhancer Substances 0.000 description 1
• BJXYHBKEQFQVES-NWDGAFQWSA-N enpatoran Chemical compound N[C@H]1CN(C[C@H](C1)C(F)(F)F)C1=C2C=CC=NC2=C(C=C1)C#N BJXYHBKEQFQVES-NWDGAFQWSA-N 0.000 description 1
• 239000002662 enteric coated tablet Substances 0.000 description 1
• 239000002702 enteric coating Substances 0.000 description 1
• 229960005139 epinephrine Drugs 0.000 description 1
• 229960001208 eplerenone Drugs 0.000 description 1
• 229960004563 eprosartan Drugs 0.000 description 1
• 238000011067 equilibration Methods 0.000 description 1
• 229960003276 erythromycin Drugs 0.000 description 1
• 229960004341 escitalopram Drugs 0.000 description 1
• 229960003745 esmolol Drugs 0.000 description 1
• SUBDBMMJDZJVOS-DEOSSOPVSA-N esomeprazole Chemical compound C([S@](=O)C1=NC2=CC=C(C=C2N1)OC)C1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-DEOSSOPVSA-N 0.000 description 1
• 229960004770 esomeprazole Drugs 0.000 description 1
• 239000003797 essential amino acid Substances 0.000 description 1
• 235000020776 essential amino acid Nutrition 0.000 description 1
• CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
• OCLXJTCGWSSVOE-UHFFFAOYSA-N ethanol etoh Chemical compound CCO.CCO OCLXJTCGWSSVOE-UHFFFAOYSA-N 0.000 description 1
• BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
• 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
• GWNFQAKCJYEJEW-UHFFFAOYSA-N ethyl 3-[8-[[4-methyl-5-[(3-methyl-4-oxophthalazin-1-yl)methyl]-1,2,4-triazol-3-yl]sulfanyl]octanoylamino]benzoate Chemical compound CCOC(=O)C1=CC(NC(=O)CCCCCCCSC2=NN=C(CC3=NN(C)C(=O)C4=CC=CC=C34)N2C)=CC=C1 GWNFQAKCJYEJEW-UHFFFAOYSA-N 0.000 description 1
• 229940012017 ethylenediamine Drugs 0.000 description 1
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
• OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 1
• 238000011156 evaluation Methods 0.000 description 1
• 230000029142 excretion Effects 0.000 description 1
• 210000003722 extracellular fluid Anatomy 0.000 description 1
• 238000000605 extraction Methods 0.000 description 1
• 208000013782 familial hemiplegic migraine 3 Diseases 0.000 description 1
• 208000031352 familial ventricular tachycardia Diseases 0.000 description 1
• XUFQPHANEAPEMJ-UHFFFAOYSA-N famotidine Chemical compound NC(N)=NC1=NC(CSCCC(N)=NS(N)(=O)=O)=CS1 XUFQPHANEAPEMJ-UHFFFAOYSA-N 0.000 description 1
• RZTAMFZIAATZDJ-UHFFFAOYSA-N felodipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC(Cl)=C1Cl RZTAMFZIAATZDJ-UHFFFAOYSA-N 0.000 description 1
• 229960002428 fentanyl Drugs 0.000 description 1
• IVLVTNPOHDFFCJ-UHFFFAOYSA-N fentanyl citrate Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.C=1C=CC=CC=1N(C(=O)CC)C(CC1)CCN1CCC1=CC=CC=C1 IVLVTNPOHDFFCJ-UHFFFAOYSA-N 0.000 description 1
• 230000001605 fetal effect Effects 0.000 description 1
• 239000012467 final product Substances 0.000 description 1
• 239000000796 flavoring agent Substances 0.000 description 1
• 239000012530 fluid Substances 0.000 description 1
• 239000007850 fluorescent dye Substances 0.000 description 1
• 108010021843 fluorescent protein 583 Proteins 0.000 description 1
• 125000001153 fluoro group Chemical group F* 0.000 description 1
• 229960002464 fluoxetine Drugs 0.000 description 1
• 229960003765 fluvastatin Drugs 0.000 description 1
• 235000013355 food flavoring agent Nutrition 0.000 description 1
• 235000003599 food sweetener Nutrition 0.000 description 1
• 229960002490 fosinopril Drugs 0.000 description 1
• 238000007710 freezing Methods 0.000 description 1
• 239000001530 fumaric acid Substances 0.000 description 1
• 235000011087 fumaric acid Nutrition 0.000 description 1
• ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
• 125000002541 furyl group Chemical group 0.000 description 1
• 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
• 239000007789 gas Substances 0.000 description 1
• 208000018685 gastrointestinal system disease Diseases 0.000 description 1
• 210000001035 gastrointestinal tract Anatomy 0.000 description 1
• 229960002518 gentamicin Drugs 0.000 description 1
• 239000000174 gluconic acid Substances 0.000 description 1
• 235000012208 gluconic acid Nutrition 0.000 description 1
• 229960002442 glucosamine Drugs 0.000 description 1
• 229960002972 glutethimide Drugs 0.000 description 1
• 125000005456 glyceride group Chemical group 0.000 description 1
• 229960003711 glyceryl trinitrate Drugs 0.000 description 1
• 238000005469 granulation Methods 0.000 description 1
• 230000003179 granulation Effects 0.000 description 1
• 229960004553 guanabenz Drugs 0.000 description 1
• 229960003050 guanabenz acetate Drugs 0.000 description 1
• 229960003602 guanethidine Drugs 0.000 description 1
• YUFWAVFNITUSHI-UHFFFAOYSA-N guanethidine monosulfate Chemical compound [H+].[H+].[O-]S([O-])(=O)=O.NC(=N)NCCN1CCCCCCC1 YUFWAVFNITUSHI-UHFFFAOYSA-N 0.000 description 1
• 229960004746 guanfacine hydrochloride Drugs 0.000 description 1
• 230000036541 health Effects 0.000 description 1
• 210000002064 heart cell Anatomy 0.000 description 1
• 230000010247 heart contraction Effects 0.000 description 1
• 208000038003 heart failure with preserved ejection fraction Diseases 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• 229920000669 heparin Polymers 0.000 description 1
• 125000005241 heteroarylamino group Chemical group 0.000 description 1
• HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
• 229960002885 histidine Drugs 0.000 description 1
• 239000008240 homogeneous mixture Substances 0.000 description 1
• 102000049589 human SCN1A Human genes 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
• 150000004678 hydrides Chemical class 0.000 description 1
• 229960002003 hydrochlorothiazide Drugs 0.000 description 1
• 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 1
• CUILPNURFADTPE-UHFFFAOYSA-N hypobromous acid Chemical class BrO CUILPNURFADTPE-UHFFFAOYSA-N 0.000 description 1
• 238000003384 imaging method Methods 0.000 description 1
• 230000000937 inactivator Effects 0.000 description 1
• MGXWVYUBJRZYPE-YUGYIWNOSA-N incretin Chemical class C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCC(N)=O)C(O)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1C=CC(O)=CC=1)[C@@H](C)O)[C@@H](C)CC)C1=CC=C(O)C=C1 MGXWVYUBJRZYPE-YUGYIWNOSA-N 0.000 description 1
• 239000000859 incretin Substances 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
• HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 description 1
• 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
• 229960000905 indomethacin Drugs 0.000 description 1
• 239000011261 inert gas Substances 0.000 description 1
• 229940097708 inspra Drugs 0.000 description 1
• 229940125396 insulin Drugs 0.000 description 1
• 238000001361 intraarterial administration Methods 0.000 description 1
• 230000003834 intracellular effect Effects 0.000 description 1
• 238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
• 238000007918 intramuscular administration Methods 0.000 description 1
• 238000007912 intraperitoneal administration Methods 0.000 description 1
• 238000001990 intravenous administration Methods 0.000 description 1
• 239000011630 iodine Chemical group 0.000 description 1
• 150000002500 ions Chemical class 0.000 description 1
• 229960001361 ipratropium bromide Drugs 0.000 description 1
• KEWHKYJURDBRMN-ZEODDXGYSA-M ipratropium bromide hydrate Chemical compound O.[Br-].O([C@H]1C[C@H]2CC[C@@H](C1)[N@@+]2(C)C(C)C)C(=O)C(CO)C1=CC=CC=C1 KEWHKYJURDBRMN-ZEODDXGYSA-M 0.000 description 1
• YOSHYTLCDANDAN-UHFFFAOYSA-N irbesartan Chemical compound O=C1N(CC=2C=CC(=CC=2)C=2C(=CC=CC=2)C=2NN=NN=2)C(CCCC)=NC21CCCC2 YOSHYTLCDANDAN-UHFFFAOYSA-N 0.000 description 1
• 230000001788 irregular Effects 0.000 description 1
• 230000000302 ischemic effect Effects 0.000 description 1
• JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
• MOYKHGMNXAOIAT-JGWLITMVSA-N isosorbide dinitrate Chemical compound [O-][N+](=O)O[C@H]1CO[C@@H]2[C@H](O[N+](=O)[O-])CO[C@@H]21 MOYKHGMNXAOIAT-JGWLITMVSA-N 0.000 description 1
• 229960000201 isosorbide dinitrate Drugs 0.000 description 1
• YWXYYJSYQOXTPL-SLPGGIOYSA-N isosorbide mononitrate Chemical compound [O-][N+](=O)O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 YWXYYJSYQOXTPL-SLPGGIOYSA-N 0.000 description 1
• 229960003827 isosorbide mononitrate Drugs 0.000 description 1
• ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
• 239000007951 isotonicity adjuster Substances 0.000 description 1
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
• 210000004731 jugular vein Anatomy 0.000 description 1
• 229940090589 keflex Drugs 0.000 description 1
• 229940072289 kerlone Drugs 0.000 description 1
• 125000000468 ketone group Chemical group 0.000 description 1
• 150000002576 ketones Chemical class 0.000 description 1
• 238000010983 kinetics study Methods 0.000 description 1
• 229960003174 lansoprazole Drugs 0.000 description 1
• 239000000787 lecithin Substances 0.000 description 1
• 235000010445 lecithin Nutrition 0.000 description 1
• 229940067606 lecithin Drugs 0.000 description 1
• 210000002414 leg Anatomy 0.000 description 1
• OTQCKZUSUGYWBD-BRHMIFOHSA-N lepirudin Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CS)C(=O)N[C@H](C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CS)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCC(O)=O)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@H](C(=O)N[C@@H](CS)C(=O)NCC(=O)N[C@@H](CCC(N)=O)C(=O)NCC(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CS)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(O)=O)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CS)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(O)=O)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(O)=O)C(C)C)[C@@H](C)O)[C@@H](C)O)NC(=O)[C@@H](NC(=O)[C@@H](N)CC(C)C)[C@@H](C)O)C1=CC=C(O)C=C1 OTQCKZUSUGYWBD-BRHMIFOHSA-N 0.000 description 1
• 229960004408 lepirudin Drugs 0.000 description 1
• 229940095570 lescol Drugs 0.000 description 1
• 229940054157 lexapro Drugs 0.000 description 1
• 229960004194 lidocaine Drugs 0.000 description 1
• 229940041028 lincosamides Drugs 0.000 description 1
• TYZROVQLWOKYKF-ZDUSSCGKSA-N linezolid Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCOCC1 TYZROVQLWOKYKF-ZDUSSCGKSA-N 0.000 description 1
• 229960003907 linezolid Drugs 0.000 description 1
• 229940002661 lipitor Drugs 0.000 description 1
• 229910052744 lithium Inorganic materials 0.000 description 1
• 229940092923 livalo Drugs 0.000 description 1
• 210000004185 liver Anatomy 0.000 description 1
• RENRQMCACQEWFC-UGKGYDQZSA-N lnp023 Chemical compound C1([C@H]2N(CC=3C=4C=CNC=4C(C)=CC=3OC)CC[C@@H](C2)OCC)=CC=C(C(O)=O)C=C1 RENRQMCACQEWFC-UGKGYDQZSA-N 0.000 description 1
• 229940089504 lopressor Drugs 0.000 description 1
• 229960004391 lorazepam Drugs 0.000 description 1
• 229960004773 losartan Drugs 0.000 description 1
• 229940080268 lotensin Drugs 0.000 description 1
• 229940080288 lotrel Drugs 0.000 description 1
• 229960004844 lovastatin Drugs 0.000 description 1
• QLJODMDSTUBWDW-UHFFFAOYSA-N lovastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 QLJODMDSTUBWDW-UHFFFAOYSA-N 0.000 description 1
• 239000003055 low molecular weight heparin Substances 0.000 description 1
• 229940127215 low-molecular weight heparin Drugs 0.000 description 1
• 239000007937 lozenge Substances 0.000 description 1
• 210000004072 lung Anatomy 0.000 description 1
• 229960003646 lysine Drugs 0.000 description 1
• MRSJBSHLMOBYSH-UHFFFAOYSA-N m-Nisoldipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCC(C)C)C1C1=CC=CC([N+]([O-])=O)=C1 MRSJBSHLMOBYSH-UHFFFAOYSA-N 0.000 description 1
• 239000001115 mace Substances 0.000 description 1
• 239000003120 macrolide antibiotic agent Substances 0.000 description 1
• VEVZQDGATGBLIC-OXLUMUBXSA-N magnesium;5-methoxy-2-[(s)-(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]benzimidazol-1-ide;trihydrate Chemical compound O.O.O.[Mg+2].C([S@](=O)C=1[N-]C2=CC=C(C=C2N=1)OC)C1=NC=C(C)C(OC)=C1C.C([S@](=O)C=1[N-]C2=CC=C(C=C2N=1)OC)C1=NC=C(C)C(OC)=C1C VEVZQDGATGBLIC-OXLUMUBXSA-N 0.000 description 1
• 230000014759 maintenance of location Effects 0.000 description 1
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
• 239000011976 maleic acid Substances 0.000 description 1
• 239000001630 malic acid Chemical class 0.000 description 1
• 235000011090 malic acid Nutrition 0.000 description 1
• 229960002510 mandelic acid Drugs 0.000 description 1
• 239000003550 marker Substances 0.000 description 1
• 230000000873 masking effect Effects 0.000 description 1
• 239000011159 matrix material Substances 0.000 description 1
• 229940103179 mavik Drugs 0.000 description 1
• 229940064748 medrol Drugs 0.000 description 1
• 229960004815 meprobamate Drugs 0.000 description 1
• 230000004060 metabolic process Effects 0.000 description 1
• 239000002207 metabolite Substances 0.000 description 1
• 229940117841 methacrylic acid copolymer Drugs 0.000 description 1
• 229920003145 methacrylic acid copolymer Polymers 0.000 description 1
• 229940098779 methanesulfonic acid Drugs 0.000 description 1
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
• OJLOPKGSLYJEMD-URPKTTJQSA-N methyl 7-[(1r,2r,3r)-3-hydroxy-2-[(1e)-4-hydroxy-4-methyloct-1-en-1-yl]-5-oxocyclopentyl]heptanoate Chemical compound CCCCC(C)(O)C\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)OC OJLOPKGSLYJEMD-URPKTTJQSA-N 0.000 description 1
• ZBELDPMWYXDLNY-UHFFFAOYSA-N methyl 9-(4-bromo-2-fluoroanilino)-[1,3]thiazolo[5,4-f]quinazoline-2-carboximidate Chemical compound C12=C3SC(C(=N)OC)=NC3=CC=C2N=CN=C1NC1=CC=C(Br)C=C1F ZBELDPMWYXDLNY-UHFFFAOYSA-N 0.000 description 1
• 229920000609 methyl cellulose Polymers 0.000 description 1
• 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
• 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
• WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
• 239000001923 methylcellulose Substances 0.000 description 1
• 235000010981 methylcellulose Nutrition 0.000 description 1
• 229960002216 methylparaben Drugs 0.000 description 1
• 229960004584 methylprednisolone Drugs 0.000 description 1
• 229960002817 metolazone Drugs 0.000 description 1
• 229960002237 metoprolol Drugs 0.000 description 1
• IUBSYMUCCVWXPE-UHFFFAOYSA-N metoprolol Chemical compound COCCC1=CC=C(OCC(O)CNC(C)C)C=C1 IUBSYMUCCVWXPE-UHFFFAOYSA-N 0.000 description 1
• 229940099246 mevacor Drugs 0.000 description 1
• AJLFOPYRIVGYMJ-INTXDZFKSA-N mevastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=CCC[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 AJLFOPYRIVGYMJ-INTXDZFKSA-N 0.000 description 1
• 229950009116 mevastatin Drugs 0.000 description 1
• BOZILQFLQYBIIY-UHFFFAOYSA-N mevastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CCC=C21 BOZILQFLQYBIIY-UHFFFAOYSA-N 0.000 description 1
• DDLIGBOFAVUZHB-UHFFFAOYSA-N midazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NC=C2CN=C1C1=CC=CC=C1F DDLIGBOFAVUZHB-UHFFFAOYSA-N 0.000 description 1
• 229960003793 midazolam Drugs 0.000 description 1
• 206010027599 migraine Diseases 0.000 description 1
• 229940101635 minizide Drugs 0.000 description 1
• 229960005249 misoprostol Drugs 0.000 description 1
• 239000011812 mixed powder Substances 0.000 description 1
• 229960005170 moexipril Drugs 0.000 description 1
• 229940041009 monobactams Drugs 0.000 description 1
• 229940118178 monopril Drugs 0.000 description 1
• 229960005181 morphine Drugs 0.000 description 1
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
• 239000010413 mother solution Substances 0.000 description 1
• 210000000107 myocyte Anatomy 0.000 description 1
• 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• LXESFDLDPCOLJE-UHFFFAOYSA-N n-(2-hydroxypropyl)-2-[3-oxo-6-[4-(trifluoromethyl)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-2-yl]acetamide Chemical compound C=1N2C(=O)N(CC(=O)NCC(O)C)N=C2C=CC=1C1=CC=C(C(F)(F)F)C=C1 LXESFDLDPCOLJE-UHFFFAOYSA-N 0.000 description 1
• VQSRKMNBWMHJKY-YTEVENLXSA-N n-[3-[(4ar,7as)-2-amino-6-(5-fluoropyrimidin-2-yl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-7a-yl]-4-fluorophenyl]-5-methoxypyrazine-2-carboxamide Chemical compound C1=NC(OC)=CN=C1C(=O)NC1=CC=C(F)C([C@@]23[C@@H](CN(C2)C=2N=CC(F)=CN=2)CSC(N)=N3)=C1 VQSRKMNBWMHJKY-YTEVENLXSA-N 0.000 description 1
• YGBMCLDVRUGXOV-UHFFFAOYSA-N n-[6-[6-chloro-5-[(4-fluorophenyl)sulfonylamino]pyridin-3-yl]-1,3-benzothiazol-2-yl]acetamide Chemical compound C1=C2SC(NC(=O)C)=NC2=CC=C1C(C=1)=CN=C(Cl)C=1NS(=O)(=O)C1=CC=C(F)C=C1 YGBMCLDVRUGXOV-UHFFFAOYSA-N 0.000 description 1
• WOOWBQQQJXZGIE-UHFFFAOYSA-N n-ethyl-n-propan-2-ylpropan-2-amine Chemical compound CCN(C(C)C)C(C)C.CCN(C(C)C)C(C)C WOOWBQQQJXZGIE-UHFFFAOYSA-N 0.000 description 1
• HGUZQMQXAHVIQC-UHFFFAOYSA-N n-methylethenamine Chemical group CNC=C HGUZQMQXAHVIQC-UHFFFAOYSA-N 0.000 description 1
• IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 1
• 210000000653 nervous system Anatomy 0.000 description 1
• 230000001537 neural effect Effects 0.000 description 1
• 230000000926 neurological effect Effects 0.000 description 1
• 230000002232 neuromuscular Effects 0.000 description 1
• 210000002569 neuron Anatomy 0.000 description 1
• 230000002981 neuropathic effect Effects 0.000 description 1
• 229940112641 nexium Drugs 0.000 description 1
• 229960001783 nicardipine Drugs 0.000 description 1
• LBHIOVVIQHSOQN-UHFFFAOYSA-N nicorandil Chemical compound [O-][N+](=O)OCCNC(=O)C1=CC=CN=C1 LBHIOVVIQHSOQN-UHFFFAOYSA-N 0.000 description 1
• 229960002497 nicorandil Drugs 0.000 description 1
• UIAGMCDKSXEBJQ-UHFFFAOYSA-N nimodipine Chemical compound COCCOC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)C)C1C1=CC=CC([N+]([O-])=O)=C1 UIAGMCDKSXEBJQ-UHFFFAOYSA-N 0.000 description 1
• 229910017604 nitric acid Inorganic materials 0.000 description 1
• 229960002460 nitroprusside Drugs 0.000 description 1
• 229960004872 nizatidine Drugs 0.000 description 1
• 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
• 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
• UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
• JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
• 229940036132 norvasc Drugs 0.000 description 1
• 235000020824 obesity Nutrition 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
• 239000002674 ointment Substances 0.000 description 1
• PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 1
• 229940005483 opioid analgesics Drugs 0.000 description 1
• 238000005457 optimization Methods 0.000 description 1
• 235000005985 organic acids Nutrition 0.000 description 1
• 238000006053 organic reaction Methods 0.000 description 1
• 230000003204 osmotic effect Effects 0.000 description 1
• 235000006408 oxalic acid Nutrition 0.000 description 1
• 150000002917 oxazolidines Chemical class 0.000 description 1
• 125000004430 oxygen atom Chemical group O* 0.000 description 1
• 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
• LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 description 1
• 229940124641 pain reliever Drugs 0.000 description 1
• MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 1
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].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.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 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
• FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
• 229960005489 paracetamol Drugs 0.000 description 1
• 238000007911 parenteral administration Methods 0.000 description 1
• 229960002296 paroxetine Drugs 0.000 description 1
• 230000007310 pathophysiology Effects 0.000 description 1
• 239000000312 peanut oil Substances 0.000 description 1
• 230000035515 penetration Effects 0.000 description 1
• 229940049954 penicillin Drugs 0.000 description 1
• 150000002960 penicillins Chemical class 0.000 description 1
• QSYOAKOOQMVVTO-UHFFFAOYSA-N pentan-2-yl 2-methylprop-2-enoate Chemical compound CCCC(C)OC(=O)C(C)=C QSYOAKOOQMVVTO-UHFFFAOYSA-N 0.000 description 1
• 208000011906 peptic ulcer disease Diseases 0.000 description 1
• 229940124531 pharmaceutical excipient Drugs 0.000 description 1
• 229960003742 phenol Drugs 0.000 description 1
• 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
• 239000002504 physiological saline solution Substances 0.000 description 1
• 229960002508 pindolol Drugs 0.000 description 1
• 229960002797 pitavastatin Drugs 0.000 description 1
• VGYFMXBACGZSIL-MCBHFWOFSA-N pitavastatin Chemical compound OC(=O)C[C@H](O)C[C@H](O)\C=C\C1=C(C2CC2)N=C2C=CC=CC2=C1C1=CC=C(F)C=C1 VGYFMXBACGZSIL-MCBHFWOFSA-N 0.000 description 1
• RHGYHLPFVJEAOC-FFNUKLMVSA-L pitavastatin calcium Chemical compound [Ca+2].[O-]C(=O)C[C@H](O)C[C@H](O)\C=C\C1=C(C2CC2)N=C2C=CC=CC2=C1C1=CC=C(F)C=C1.[O-]C(=O)C[C@H](O)C[C@H](O)\C=C\C1=C(C2CC2)N=C2C=CC=CC2=C1C1=CC=C(F)C=C1 RHGYHLPFVJEAOC-FFNUKLMVSA-L 0.000 description 1
• 239000004014 plasticizer Substances 0.000 description 1
• 229920000573 polyethylene Polymers 0.000 description 1
• 229920001223 polyethylene glycol Polymers 0.000 description 1
• 229940041153 polymyxins Drugs 0.000 description 1
• 239000013641 positive control Substances 0.000 description 1
• 229960002965 pravastatin Drugs 0.000 description 1
• TUZYXOIXSAXUGO-PZAWKZKUSA-N pravastatin Chemical compound C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 TUZYXOIXSAXUGO-PZAWKZKUSA-N 0.000 description 1
• VWBQYTRBTXKKOG-IYNICTALSA-M pravastatin sodium Chemical compound [Na+].C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC([O-])=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 VWBQYTRBTXKKOG-IYNICTALSA-M 0.000 description 1
• 229960002386 prazosin hydrochloride Drugs 0.000 description 1
• 239000002244 precipitate Substances 0.000 description 1
• 238000012746 preparative thin layer chromatography Methods 0.000 description 1
• 239000003755 preservative agent Substances 0.000 description 1
• 229940032668 prevacid Drugs 0.000 description 1
• 230000002265 prevention Effects 0.000 description 1
• 150000003141 primary amines Chemical class 0.000 description 1
• 229940088953 prinivil Drugs 0.000 description 1
• 229960003081 probenecid Drugs 0.000 description 1
• DBABZHXKTCFAPX-UHFFFAOYSA-N probenecid Chemical compound CCCN(CCC)S(=O)(=O)C1=CC=C(C(O)=O)C=C1 DBABZHXKTCFAPX-UHFFFAOYSA-N 0.000 description 1
• REQCZEXYDRLIBE-UHFFFAOYSA-N procainamide Chemical compound CCN(CC)CCNC(=O)C1=CC=C(N)C=C1 REQCZEXYDRLIBE-UHFFFAOYSA-N 0.000 description 1
• 229960000244 procainamide Drugs 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
• 230000002035 prolonged effect Effects 0.000 description 1
• JWHAUXFOSRPERK-UHFFFAOYSA-N propafenone Chemical compound CCCNCC(O)COC1=CC=CC=C1C(=O)CCC1=CC=CC=C1 JWHAUXFOSRPERK-UHFFFAOYSA-N 0.000 description 1
• 229960000203 propafenone Drugs 0.000 description 1
• FZJCXIDLUFPGPP-UHFFFAOYSA-N propan-2-ol;toluene Chemical compound CC(C)O.CC1=CC=CC=C1 FZJCXIDLUFPGPP-UHFFFAOYSA-N 0.000 description 1
• 235000019260 propionic acid Nutrition 0.000 description 1
• LZFIOSVZIQOVFW-UHFFFAOYSA-N propyl 2-hydroxybenzoate Chemical class CCCOC(=O)C1=CC=CC=C1O LZFIOSVZIQOVFW-UHFFFAOYSA-N 0.000 description 1
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
• 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
• 229960003415 propylparaben Drugs 0.000 description 1
• 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
• 150000003180 prostaglandins Chemical class 0.000 description 1
• 229940126409 proton pump inhibitor Drugs 0.000 description 1
• 239000000612 proton pump inhibitor Substances 0.000 description 1
• 229940063566 proventil Drugs 0.000 description 1
• 229940035613 prozac Drugs 0.000 description 1
• 230000000541 pulsatile effect Effects 0.000 description 1
• 238000005086 pumping Methods 0.000 description 1
• 239000008213 purified water Substances 0.000 description 1
• 150000003212 purines Chemical class 0.000 description 1
• 239000002728 pyrethroid Substances 0.000 description 1
• PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
• NWELCUKYUCBVKK-UHFFFAOYSA-N pyridin-2-ylhydrazine Chemical class NNC1=CC=CC=N1 NWELCUKYUCBVKK-UHFFFAOYSA-N 0.000 description 1
• ABMYEXAYWZJVOV-UHFFFAOYSA-N pyridin-3-ylboronic acid Chemical compound OB(O)C1=CC=CN=C1 ABMYEXAYWZJVOV-UHFFFAOYSA-N 0.000 description 1
• 125000004076 pyridyl group Chemical group 0.000 description 1
• 229940107700 pyruvic acid Drugs 0.000 description 1
• 229960001455 quinapril Drugs 0.000 description 1
• JSDRRTOADPPCHY-HSQYWUDLSA-N quinapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2=CC=CC=C2C1)C(O)=O)CC1=CC=CC=C1 JSDRRTOADPPCHY-HSQYWUDLSA-N 0.000 description 1
• IBBLRJGOOANPTQ-JKVLGAQCSA-N quinapril hydrochloride Chemical compound Cl.C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2=CC=CC=C2C1)C(O)=O)CC1=CC=CC=C1 IBBLRJGOOANPTQ-JKVLGAQCSA-N 0.000 description 1
• JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical class O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
• 229960001404 quinidine Drugs 0.000 description 1
• 150000007660 quinolones Chemical class 0.000 description 1
• YREYEVIYCVEVJK-UHFFFAOYSA-N rabeprazole Chemical compound COCCCOC1=CC=NC(CS(=O)C=2NC3=CC=CC=C3N=2)=C1C YREYEVIYCVEVJK-UHFFFAOYSA-N 0.000 description 1
• 229960004157 rabeprazole Drugs 0.000 description 1
• 230000002285 radioactive effect Effects 0.000 description 1
• 238000001959 radiotherapy Methods 0.000 description 1
• HDACQVRGBOVJII-JBDAPHQKSA-N ramipril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](C[C@@H]2CCC[C@@H]21)C(O)=O)CC1=CC=CC=C1 HDACQVRGBOVJII-JBDAPHQKSA-N 0.000 description 1
• GGWBHVILAJZWKJ-KJEVSKRMSA-N ranitidine hydrochloride Chemical compound [H+].[Cl-].[O-][N+](=O)\C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 GGWBHVILAJZWKJ-KJEVSKRMSA-N 0.000 description 1
• 238000010992 reflux Methods 0.000 description 1
• 229960003147 reserpine Drugs 0.000 description 1
• 230000000241 respiratory effect Effects 0.000 description 1
• 230000000284 resting effect Effects 0.000 description 1
• 230000033764 rhythmic process Effects 0.000 description 1
• 229940081561 rocephin Drugs 0.000 description 1
• MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
• 229960000672 rosuvastatin Drugs 0.000 description 1
• BPRHUIZQVSMCRT-VEUZHWNKSA-N rosuvastatin Chemical compound CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC(O)=O BPRHUIZQVSMCRT-VEUZHWNKSA-N 0.000 description 1
• LALFOYNTGMUKGG-BGRFNVSISA-L rosuvastatin calcium Chemical compound [Ca+2].CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O.CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O LALFOYNTGMUKGG-BGRFNVSISA-L 0.000 description 1
• 238000002390 rotary evaporation Methods 0.000 description 1
• 229960002052 salbutamol Drugs 0.000 description 1
• 229960004889 salicylic acid Drugs 0.000 description 1
• 229960004017 salmeterol Drugs 0.000 description 1
• 229940100992 sarafem Drugs 0.000 description 1
• 235000003441 saturated fatty acids Nutrition 0.000 description 1
• 150000004671 saturated fatty acids Chemical class 0.000 description 1
• HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical class O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
• 229940082552 sectral Drugs 0.000 description 1
• 239000000932 sedative agent Substances 0.000 description 1
• 229940125723 sedative agent Drugs 0.000 description 1
• XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
• 229940090585 serevent Drugs 0.000 description 1
• 238000013207 serial dilution Methods 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
• 229960002073 sertraline Drugs 0.000 description 1
• 210000002966 serum Anatomy 0.000 description 1
• 239000008159 sesame oil Substances 0.000 description 1
• 235000011803 sesame oil Nutrition 0.000 description 1
• 239000004208 shellac Substances 0.000 description 1
• 229940113147 shellac Drugs 0.000 description 1
• ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
• 235000013874 shellac Nutrition 0.000 description 1
• 239000000741 silica gel Substances 0.000 description 1
• 229910002027 silica gel Inorganic materials 0.000 description 1
• 238000010898 silica gel chromatography Methods 0.000 description 1
• 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
• XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
• RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 description 1
• 235000017550 sodium carbonate Nutrition 0.000 description 1
• 229910000029 sodium carbonate Inorganic materials 0.000 description 1
• 239000012312 sodium hydride Substances 0.000 description 1
• KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 1
• 229940054269 sodium pyruvate Drugs 0.000 description 1
• AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
• 235000019345 sodium thiosulphate Nutrition 0.000 description 1
• 229940087854 solu-medrol Drugs 0.000 description 1
• 239000004334 sorbic acid Substances 0.000 description 1
• 235000010199 sorbic acid Nutrition 0.000 description 1
• 229940075582 sorbic acid Drugs 0.000 description 1
• 239000000600 sorbitol Substances 0.000 description 1
• 235000010356 sorbitol Nutrition 0.000 description 1
• VIDRYROWYFWGSY-UHFFFAOYSA-N sotalol hydrochloride Chemical compound Cl.CC(C)NCC(O)C1=CC=C(NS(C)(=O)=O)C=C1 VIDRYROWYFWGSY-UHFFFAOYSA-N 0.000 description 1
• 229940046810 spiriva Drugs 0.000 description 1
• 229960002256 spironolactone Drugs 0.000 description 1
• 238000013222 sprague-dawley male rat Methods 0.000 description 1
• 230000006641 stabilisation Effects 0.000 description 1
• 238000011105 stabilization Methods 0.000 description 1
• 239000008117 stearic acid Substances 0.000 description 1
• 230000000707 stereoselective effect Effects 0.000 description 1
• 239000012058 sterile packaged powder Substances 0.000 description 1
• 230000001954 sterilising effect Effects 0.000 description 1
• 238000004659 sterilization and disinfection Methods 0.000 description 1
• 230000004936 stimulating effect Effects 0.000 description 1
• 229940041030 streptogramins Drugs 0.000 description 1
• 229960005202 streptokinase Drugs 0.000 description 1
• 229960005322 streptomycin Drugs 0.000 description 1
• 239000000758 substrate Substances 0.000 description 1
• 229960004291 sucralfate Drugs 0.000 description 1
• 235000000346 sugar Nutrition 0.000 description 1
• 150000008163 sugars Chemical class 0.000 description 1
• 229960000654 sulfafurazole Drugs 0.000 description 1
• MBGGBVCUIVRRBF-UHFFFAOYSA-N sulfinpyrazone Chemical compound O=C1N(C=2C=CC=CC=2)N(C=2C=CC=CC=2)C(=O)C1CCS(=O)C1=CC=CC=C1 MBGGBVCUIVRRBF-UHFFFAOYSA-N 0.000 description 1
• 229960003329 sulfinpyrazone Drugs 0.000 description 1
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
• 239000006228 supernatant Substances 0.000 description 1
• 229940072226 suprax Drugs 0.000 description 1
• 239000004094 surface-active agent Substances 0.000 description 1
• 239000000375 suspending agent Substances 0.000 description 1
• 230000002459 sustained effect Effects 0.000 description 1
• 238000013268 sustained release Methods 0.000 description 1
• 239000012730 sustained-release form Substances 0.000 description 1
• 230000009747 swallowing Effects 0.000 description 1
• 239000003765 sweetening agent Substances 0.000 description 1
• 208000011580 syndromic disease Diseases 0.000 description 1
• 230000002195 synergetic effect Effects 0.000 description 1
• 238000001308 synthesis method Methods 0.000 description 1
• 230000009897 systematic effect Effects 0.000 description 1
• 229940066769 systemic antihistamines substituted alkylamines Drugs 0.000 description 1
• 230000009885 systemic effect Effects 0.000 description 1
• 238000004885 tandem mass spectrometry Methods 0.000 description 1
• 239000011975 tartaric acid Substances 0.000 description 1
• 235000002906 tartaric acid Nutrition 0.000 description 1
• RMMXLENWKUUMAY-UHFFFAOYSA-N telmisartan Chemical compound CCCC1=NC2=C(C)C=C(C=3N(C4=CC=CC=C4N=3)C)C=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C(O)=O RMMXLENWKUUMAY-UHFFFAOYSA-N 0.000 description 1
• 229960000216 tenecteplase Drugs 0.000 description 1
• 229940065385 tenex Drugs 0.000 description 1
• 229940108485 tenormin Drugs 0.000 description 1
• 229960001909 terazosin hydrochloride Drugs 0.000 description 1
• 229960000195 terbutaline Drugs 0.000 description 1
• 239000012085 test solution Substances 0.000 description 1
• MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 1
• WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
• KTAVBOYXMBQFGR-MAODNAKNSA-J tetrasodium;(6r,7r)-7-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyimino-1-oxidoethylidene]amino]-3-[(2-methyl-5,6-dioxo-1h-1,2,4-triazin-3-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate;heptahydrate Chemical compound O.O.O.O.O.O.O.[Na+].[Na+].[Na+].[Na+].S([C@@H]1[C@@H](C(N1C=1C([O-])=O)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1CSC1=NC(=O)C([O-])=NN1C.S([C@@H]1[C@@H](C(N1C=1C([O-])=O)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1CSC1=NC(=O)C([O-])=NN1C KTAVBOYXMBQFGR-MAODNAKNSA-J 0.000 description 1
• 229940078806 teveten Drugs 0.000 description 1
• WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
• 229960004559 theobromine Drugs 0.000 description 1
• 229960000278 theophylline Drugs 0.000 description 1
• 231100001274 therapeutic index Toxicity 0.000 description 1
• RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
• 229940033663 thimerosal Drugs 0.000 description 1
• 229930192474 thiophene Natural products 0.000 description 1
• 229940035248 tiazac Drugs 0.000 description 1
• PHWBOXQYWZNQIN-UHFFFAOYSA-N ticlopidine Chemical compound ClC1=CC=CC=C1CN1CC(C=CS2)=C2CC1 PHWBOXQYWZNQIN-UHFFFAOYSA-N 0.000 description 1
• 229960005001 ticlopidine Drugs 0.000 description 1
• LERNTVKEWCAPOY-DZZGSBJMSA-N tiotropium Chemical compound O([C@H]1C[C@@H]2[N+]([C@H](C1)[C@@H]1[C@H]2O1)(C)C)C(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 LERNTVKEWCAPOY-DZZGSBJMSA-N 0.000 description 1
• 229940110309 tiotropium Drugs 0.000 description 1
• 229960000707 tobramycin Drugs 0.000 description 1
• NLVFBUXFDBBNBW-PBSUHMDJSA-N tobramycin Chemical compound N[C@@H]1C[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N NLVFBUXFDBBNBW-PBSUHMDJSA-N 0.000 description 1
• 230000000699 topical effect Effects 0.000 description 1
• 235000010487 tragacanth Nutrition 0.000 description 1
• 239000000196 tragacanth Substances 0.000 description 1
• 229940116362 tragacanth Drugs 0.000 description 1
• 229960002051 trandolapril Drugs 0.000 description 1
• 239000003204 tranquilizing agent Substances 0.000 description 1
• 230000002936 tranquilizing effect Effects 0.000 description 1
• 230000009466 transformation Effects 0.000 description 1
• 238000000844 transformation Methods 0.000 description 1
• 238000003146 transient transfection Methods 0.000 description 1
• 230000007704 transition Effects 0.000 description 1
• 229960003991 trazodone Drugs 0.000 description 1
• 125000005259 triarylamine group Chemical group 0.000 description 1
• QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
• STMPXDBGVJZCEX-UHFFFAOYSA-N triethylsilyl trifluoromethanesulfonate Chemical compound CC[Si](CC)(CC)OS(=O)(=O)C(F)(F)F STMPXDBGVJZCEX-UHFFFAOYSA-N 0.000 description 1
• YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
• LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
• 229910052722 tritium Inorganic materials 0.000 description 1
• 229960000281 trometamol Drugs 0.000 description 1
• 239000012588 trypsin Substances 0.000 description 1
• 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
• 229940054495 univasc Drugs 0.000 description 1
• 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
• 210000000689 upper leg Anatomy 0.000 description 1
• 229960005356 urokinase Drugs 0.000 description 1
• 238000001291 vacuum drying Methods 0.000 description 1
• ACWBQPMHZXGDFX-QFIPXVFZSA-N valsartan Chemical compound C1=CC(CN(C(=O)CCCC)[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=CC=C1C1=NN=NN1 ACWBQPMHZXGDFX-QFIPXVFZSA-N 0.000 description 1
• MYPYJXKWCTUITO-LYRMYLQWSA-N vancomycin Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-N 0.000 description 1
• 229960003165 vancomycin Drugs 0.000 description 1
• MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 description 1
• 229940054969 vantin Drugs 0.000 description 1
• 230000002792 vascular Effects 0.000 description 1
• 229940099259 vaseline Drugs 0.000 description 1
• 235000015112 vegetable and seed oil Nutrition 0.000 description 1
• 239000008158 vegetable oil Substances 0.000 description 1
• 229940049588 velosef Drugs 0.000 description 1
• 229960004688 venlafaxine Drugs 0.000 description 1
• QYRYFNHXARDNFZ-UHFFFAOYSA-N venlafaxine hydrochloride Chemical compound [H+].[Cl-].C1=CC(OC)=CC=C1C(CN(C)C)C1(O)CCCCC1 QYRYFNHXARDNFZ-UHFFFAOYSA-N 0.000 description 1
• 208000003663 ventricular fibrillation Diseases 0.000 description 1
• FVECELJHCSPHKY-JLSHOZRYSA-N veratridine Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)O[C@@H]1[C@@]2(O)O[C@]34C[C@@]5(O)[C@H](CN6[C@@H](CC[C@H](C)C6)[C@@]6(C)O)[C@]6(O)[C@@H](O)C[C@@]5(O)[C@@H]4CC[C@H]2[C@]3(C)CC1 FVECELJHCSPHKY-JLSHOZRYSA-N 0.000 description 1
• 229940055010 verelan Drugs 0.000 description 1
• 229920002554 vinyl polymer Polymers 0.000 description 1
• 210000001835 viscera Anatomy 0.000 description 1
• 229940063670 visken Drugs 0.000 description 1
• 238000003260 vortexing Methods 0.000 description 1
• 229960005080 warfarin Drugs 0.000 description 1
• 239000003021 water soluble solvent Substances 0.000 description 1
• 238000005303 weighing Methods 0.000 description 1
• 229940009065 wellbutrin Drugs 0.000 description 1
• 239000000080 wetting agent Substances 0.000 description 1
• 229940087514 zaroxolyn Drugs 0.000 description 1
• 229940052204 zebeta Drugs 0.000 description 1
• 229940117978 ziac Drugs 0.000 description 1
• 229940020965 zoloft Drugs 0.000 description 1
• 229940018503 zyban Drugs 0.000 description 1
• 239000002132 β-lactam antibiotic Substances 0.000 description 1
• 229940124586 β-lactam antibiotics Drugs 0.000 description 1