NZ534539A - 2-oxazolamines and their use as 5-HT2B receptor antagonists - Google Patents

Info

Publication number

NZ534539A

NZ534539A NZ534539A NZ53453903A NZ534539A NZ 534539 A NZ534539 A NZ 534539A NZ 534539 A NZ534539 A NZ 534539A NZ 53453903 A NZ53453903 A NZ 53453903A NZ 534539 A NZ534539 A NZ 534539A

Authority

NZ

New Zealand

Prior art keywords

alkyl

optionally substituted

group

compound according

amino

Prior art date

2002-02-13

Links

• Espacenet
• Global Dossier
• Discuss

• 102000006969 5-HT2B Serotonin Receptor Human genes 0.000 title claims abstract description 20
• 108010072584 5-HT2B Serotonin Receptor Proteins 0.000 title claims description 13
• ACTKAGSPIFDCMF-UHFFFAOYSA-N 1,3-oxazol-2-amine Chemical class NC1=NC=CO1 ACTKAGSPIFDCMF-UHFFFAOYSA-N 0.000 title description 4
• 229940044551 receptor antagonist Drugs 0.000 title description 4
• 239000002464 receptor antagonist Substances 0.000 title description 4
• 150000001875 compounds Chemical class 0.000 claims abstract description 120
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 12
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract description 12
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 8
• 238000002360 preparation method Methods 0.000 claims abstract description 7
• 238000011282 treatment Methods 0.000 claims abstract description 7
• 230000008485 antagonism Effects 0.000 claims abstract description 6
• 239000003814 drug Substances 0.000 claims abstract description 4
• -1 cyano, amino Chemical group 0.000 claims description 85
• 125000000217 alkyl group Chemical group 0.000 claims description 74
• 238000000034 method Methods 0.000 claims description 62
• 125000003118 aryl group Chemical group 0.000 claims description 47
• 150000003839 salts Chemical class 0.000 claims description 28
• 229910052739 hydrogen Inorganic materials 0.000 claims description 26
• 125000001424 substituent group Chemical group 0.000 claims description 26
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
• 239000001257 hydrogen Substances 0.000 claims description 20
• 125000003368 amide group Chemical group 0.000 claims description 18
• 125000005488 carboaryl group Chemical group 0.000 claims description 17
• 125000003545 alkoxy group Chemical group 0.000 claims description 14
• 239000012453 solvate Substances 0.000 claims description 13
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 12
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
• 239000008194 pharmaceutical composition Substances 0.000 claims description 6
• 239000003085 diluting agent Substances 0.000 claims description 4
• 238000002560 therapeutic procedure Methods 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 3
• 210000001035 gastrointestinal tract Anatomy 0.000 claims description 3
• 125000001475 halogen functional group Chemical group 0.000 claims 12
• 101150075901 htr2 gene Proteins 0.000 abstract description 6
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 119
• 239000000203 mixture Substances 0.000 description 107
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 91
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 63
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 60
• 239000007787 solid Substances 0.000 description 60
• 238000003786 synthesis reaction Methods 0.000 description 55
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 54
• 230000015572 biosynthetic process Effects 0.000 description 54
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 53
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 46
• 238000005481 NMR spectroscopy Methods 0.000 description 42
• 238000005160 1H NMR spectroscopy Methods 0.000 description 41
• 239000000243 solution Substances 0.000 description 39
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 38
• 238000001819 mass spectrum Methods 0.000 description 34
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 33
• 239000012267 brine Substances 0.000 description 32
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 32
• 230000002829 reductive effect Effects 0.000 description 30
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 28
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 27
• 229910052938 sodium sulfate Inorganic materials 0.000 description 27
• 235000011152 sodium sulphate Nutrition 0.000 description 27
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 26
• 239000002904 solvent Substances 0.000 description 25
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
• QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 24
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 22
• 150000002148 esters Chemical class 0.000 description 21
• 238000010992 reflux Methods 0.000 description 21
• 101150041968 CDC13 gene Proteins 0.000 description 20
• 125000000623 heterocyclic group Chemical group 0.000 description 19
• 239000003208 petroleum Substances 0.000 description 19
• 239000012044 organic layer Substances 0.000 description 18
• 239000003921 oil Substances 0.000 description 17
• 235000019198 oils Nutrition 0.000 description 17
• 125000006413 ring segment Chemical group 0.000 description 17
• 125000003277 amino group Chemical group 0.000 description 16
• 238000006243 chemical reaction Methods 0.000 description 15
• 238000010898 silica gel chromatography Methods 0.000 description 15
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 14
• 235000019341 magnesium sulphate Nutrition 0.000 description 14
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
• JUWCKQWZKLRALF-UHFFFAOYSA-N 5-(7-bromonaphthalen-1-yl)-1,3-oxazol-2-amine Chemical compound O1C(N)=NC=C1C1=CC=CC2=CC=C(Br)C=C12 JUWCKQWZKLRALF-UHFFFAOYSA-N 0.000 description 13
• 238000004440 column chromatography Methods 0.000 description 13
• VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 12
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
• 230000027455 binding Effects 0.000 description 12
• 238000001816 cooling Methods 0.000 description 12
• 125000000524 functional group Chemical group 0.000 description 12
• 239000012528 membrane Substances 0.000 description 12
• 239000001632 sodium acetate Substances 0.000 description 12
• 235000017281 sodium acetate Nutrition 0.000 description 12
• 238000012360 testing method Methods 0.000 description 12
• RTKUGSSNEWHBGJ-UHFFFAOYSA-N 5-naphthalen-1-yl-1,3-oxazol-2-amine Chemical compound O1C(N)=NC=C1C1=CC=CC2=CC=CC=C12 RTKUGSSNEWHBGJ-UHFFFAOYSA-N 0.000 description 11
• XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 11
• AWMZQHKHKGWNFG-UHFFFAOYSA-N 4-methyl-5-naphthalen-1-yl-1,3-oxazol-2-amine Chemical compound N1=C(N)OC(C=2C3=CC=CC=C3C=CC=2)=C1C AWMZQHKHKGWNFG-UHFFFAOYSA-N 0.000 description 10
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
• 238000003556 assay Methods 0.000 description 10
• 150000002431 hydrogen Chemical class 0.000 description 10
• MDGINGKDAPKJSJ-UHFFFAOYSA-N 5-(2-methylnaphthalen-1-yl)-1,3-oxazol-2-amine Chemical compound CC1=CC=C2C=CC=CC2=C1C1=CN=C(N)O1 MDGINGKDAPKJSJ-UHFFFAOYSA-N 0.000 description 9
• SZKFDPNRGOMFLP-UHFFFAOYSA-N 5-methyl-4-naphthalen-1-yl-1,3-oxazol-2-amine Chemical compound O1C(N)=NC(C=2C3=CC=CC=C3C=CC=2)=C1C SZKFDPNRGOMFLP-UHFFFAOYSA-N 0.000 description 9
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
• 239000002253 acid Substances 0.000 description 9
• 125000003342 alkenyl group Chemical group 0.000 description 9
• 125000004432 carbon atom Chemical group C* 0.000 description 9
• 125000001072 heteroaryl group Chemical group 0.000 description 9
• 238000004452 microanalysis Methods 0.000 description 9
• 239000012074 organic phase Substances 0.000 description 9
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 8
• UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 8
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
• 125000000304 alkynyl group Chemical group 0.000 description 8
• 239000000872 buffer Substances 0.000 description 8
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 8
• GXMIEDXDAFWVMV-UHFFFAOYSA-N 5-(2-ethoxynaphthalen-1-yl)-1,3-oxazol-2-amine Chemical compound CCOC1=CC=C2C=CC=CC2=C1C1=CN=C(N)O1 GXMIEDXDAFWVMV-UHFFFAOYSA-N 0.000 description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 7
• 125000004122 cyclic group Chemical group 0.000 description 7
• 208000035475 disorder Diseases 0.000 description 7
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
• 229910052757 nitrogen Inorganic materials 0.000 description 7
• 125000004433 nitrogen atom Chemical group N* 0.000 description 7
• 229920006395 saturated elastomer Polymers 0.000 description 7
• CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 7
• PRXNKYBFWAWBNZ-UHFFFAOYSA-N trimethylphenylammonium tribromide Chemical compound Br[Br-]Br.C[N+](C)(C)C1=CC=CC=C1 PRXNKYBFWAWBNZ-UHFFFAOYSA-N 0.000 description 7
• CJGCTDBRXYWKLJ-UHFFFAOYSA-N 1-(2-amino-1,3-oxazol-5-yl)naphthalen-2-ol Chemical compound O1C(N)=NC=C1C1=C(O)C=CC2=CC=CC=C12 CJGCTDBRXYWKLJ-UHFFFAOYSA-N 0.000 description 6
• QQLIGMASAVJVON-UHFFFAOYSA-N 1-naphthalen-1-ylethanone Chemical compound C1=CC=C2C(C(=O)C)=CC=CC2=C1 QQLIGMASAVJVON-UHFFFAOYSA-N 0.000 description 6
• QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 6
• AAKMQSSLEYOWCJ-UHFFFAOYSA-N 5-(2-phenylmethoxynaphthalen-1-yl)-1,3-oxazol-2-amine Chemical compound O1C(N)=NC=C1C(C1=CC=CC=C1C=C1)=C1OCC1=CC=CC=C1 AAKMQSSLEYOWCJ-UHFFFAOYSA-N 0.000 description 6
• IHIRLPFAMFULTN-UHFFFAOYSA-N 5-(4-fluoronaphthalen-1-yl)-1,3-oxazol-2-amine Chemical compound O1C(N)=NC=C1C1=CC=C(F)C2=CC=CC=C12 IHIRLPFAMFULTN-UHFFFAOYSA-N 0.000 description 6
• QQGFVHLDJIRGAD-UHFFFAOYSA-N 5-(4-fluoronaphthalen-1-yl)-4-propan-2-yl-1,3-oxazol-2-amine Chemical compound N1=C(N)OC(C=2C3=CC=CC=C3C(F)=CC=2)=C1C(C)C QQGFVHLDJIRGAD-UHFFFAOYSA-N 0.000 description 6
• RINLZIBNUMZSIU-UHFFFAOYSA-N 5-(5-bromonaphthalen-1-yl)-1,3-oxazol-2-amine Chemical compound O1C(N)=NC=C1C1=CC=CC2=C(Br)C=CC=C12 RINLZIBNUMZSIU-UHFFFAOYSA-N 0.000 description 6
• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
• 235000019502 Orange oil Nutrition 0.000 description 6
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 6
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
• 229910052799 carbon Inorganic materials 0.000 description 6
• HGGNZMUHOHGHBJ-UHFFFAOYSA-N dioxepane Chemical compound C1CCOOCC1 HGGNZMUHOHGHBJ-UHFFFAOYSA-N 0.000 description 6
• DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 6
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
• 239000010502 orange oil Substances 0.000 description 6
• 239000002287 radioligand Substances 0.000 description 6
• 102000005962 receptors Human genes 0.000 description 6
• 108020003175 receptors Proteins 0.000 description 6
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
• FGZJTYQVOKKPSJ-UHFFFAOYSA-N 2-bromo-1-naphthalen-1-ylpropan-1-one Chemical compound C1=CC=C2C(C(=O)C(Br)C)=CC=CC2=C1 FGZJTYQVOKKPSJ-UHFFFAOYSA-N 0.000 description 5
• FOGFUUCOYYAMJY-UHFFFAOYSA-N 4-(chloromethyl)-5-naphthalen-1-yl-1,3-oxazol-2-amine Chemical compound O1C(N)=NC(CCl)=C1C1=CC=CC2=CC=CC=C12 FOGFUUCOYYAMJY-UHFFFAOYSA-N 0.000 description 5
• VUAACLKHMWJPRQ-UHFFFAOYSA-N 5-(1-benzothiophen-4-yl)-1,3-oxazol-2-amine Chemical compound O1C(N)=NC=C1C1=CC=CC2=C1C=CS2 VUAACLKHMWJPRQ-UHFFFAOYSA-N 0.000 description 5
• SGUQKFLIBQJNHK-UHFFFAOYSA-N 5-(1-methoxynaphthalen-2-yl)-1,3-oxazol-2-amine Chemical compound C1=CC2=CC=CC=C2C(OC)=C1C1=CN=C(N)O1 SGUQKFLIBQJNHK-UHFFFAOYSA-N 0.000 description 5
• VWGJDMDZXQQUEW-UHFFFAOYSA-N 5-(2-methoxynaphthalen-1-yl)-4-methyl-1,3-oxazol-2-amine Chemical compound COC1=CC=C2C=CC=CC2=C1C=1OC(N)=NC=1C VWGJDMDZXQQUEW-UHFFFAOYSA-N 0.000 description 5
• DQOJGEOSLMWDKT-UHFFFAOYSA-N 5-(3-methyl-1-benzothiophen-2-yl)-1,3-oxazol-2-amine Chemical compound S1C2=CC=CC=C2C(C)=C1C1=CN=C(N)O1 DQOJGEOSLMWDKT-UHFFFAOYSA-N 0.000 description 5
• CQEILIPORAYCBQ-UHFFFAOYSA-N 5-(4-methoxynaphthalen-1-yl)-1,3-oxazol-2-amine Chemical compound C12=CC=CC=C2C(OC)=CC=C1C1=CN=C(N)O1 CQEILIPORAYCBQ-UHFFFAOYSA-N 0.000 description 5
• RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 5
• 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 5
• 241000244155 Taenia Species 0.000 description 5
• 239000004480 active ingredient Substances 0.000 description 5
• 150000001408 amides Chemical group 0.000 description 5
• 239000005557 antagonist Substances 0.000 description 5
• 239000012131 assay buffer Substances 0.000 description 5
• 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 5
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 5
• 150000001721 carbon Chemical group 0.000 description 5
• 210000001072 colon Anatomy 0.000 description 5
• 230000000694 effects Effects 0.000 description 5
• 239000000706 filtrate Substances 0.000 description 5
• 238000009472 formulation Methods 0.000 description 5
• 125000005843 halogen group Chemical group 0.000 description 5
• 125000005842 heteroatom Chemical group 0.000 description 5
• 125000000468 ketone group Chemical group 0.000 description 5
• 239000010410 layer Substances 0.000 description 5
• QLROYLGTNGVRBM-UHFFFAOYSA-N methyl 2-[1-(2-amino-1,3-oxazol-5-yl)naphthalen-2-yl]oxyacetate Chemical compound COC(=O)COC1=CC=C2C=CC=CC2=C1C1=CN=C(N)O1 QLROYLGTNGVRBM-UHFFFAOYSA-N 0.000 description 5
• UKEOUNLPPHKRLM-UHFFFAOYSA-N n-(5-naphthalen-1-yl-1,3-oxazol-2-yl)acetamide Chemical compound O1C(NC(=O)C)=NC=C1C1=CC=CC2=CC=CC=C12 UKEOUNLPPHKRLM-UHFFFAOYSA-N 0.000 description 5
• 231100000252 nontoxic Toxicity 0.000 description 5
• 230000003000 nontoxic effect Effects 0.000 description 5
• 238000000746 purification Methods 0.000 description 5
• 235000017557 sodium bicarbonate Nutrition 0.000 description 5
• 239000000126 substance Substances 0.000 description 5
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 4
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 4
• FWYAWAVMEZKFQD-UHFFFAOYSA-N 2-hydroxy-1-naphthalen-1-ylpropan-1-one Chemical compound C1=CC=C2C(C(=O)C(O)C)=CC=CC2=C1 FWYAWAVMEZKFQD-UHFFFAOYSA-N 0.000 description 4
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 4
• JZIBVTUXIVIFGC-UHFFFAOYSA-N 2H-pyrrole Chemical compound C1C=CC=N1 JZIBVTUXIVIFGC-UHFFFAOYSA-N 0.000 description 4
• JVQIKJMSUIMUDI-UHFFFAOYSA-N 3-pyrroline Chemical compound C1NCC=C1 JVQIKJMSUIMUDI-UHFFFAOYSA-N 0.000 description 4
• UICAOUKMLAUPJD-UHFFFAOYSA-N 4-(2-methoxynaphthalen-1-yl)-1,3-oxazol-2-amine Chemical compound COC1=CC=C2C=CC=CC2=C1C1=COC(N)=N1 UICAOUKMLAUPJD-UHFFFAOYSA-N 0.000 description 4
• 102000006902 5-HT2C Serotonin Receptor Human genes 0.000 description 4
• IEKFWQJSLUXYLD-UHFFFAOYSA-N 5-naphthalen-2-yl-1,3-oxazol-2-amine Chemical compound O1C(N)=NC=C1C1=CC=C(C=CC=C2)C2=C1 IEKFWQJSLUXYLD-UHFFFAOYSA-N 0.000 description 4
• WEEOEFBRNFILAQ-UHFFFAOYSA-N 8-(2-amino-1,3-oxazol-5-yl)naphthalene-2-carboxamide Chemical compound C12=CC(C(=O)N)=CC=C2C=CC=C1C1=CN=C(N)O1 WEEOEFBRNFILAQ-UHFFFAOYSA-N 0.000 description 4
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
• 229930194542 Keto Natural products 0.000 description 4
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
• DPWPWRLQFGFJFI-UHFFFAOYSA-N Pargyline Chemical compound C#CCN(C)CC1=CC=CC=C1 DPWPWRLQFGFJFI-UHFFFAOYSA-N 0.000 description 4
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
• 150000001409 amidines Chemical class 0.000 description 4
• 125000000129 anionic group Chemical group 0.000 description 4
• 239000008346 aqueous phase Substances 0.000 description 4
• 125000004429 atom Chemical group 0.000 description 4
• CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 4
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
• 239000000969 carrier Substances 0.000 description 4
• 239000001913 cellulose Chemical class 0.000 description 4
• 229920002678 cellulose Chemical class 0.000 description 4
• NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 4
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 4
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 4
• 239000000284 extract Substances 0.000 description 4
• 238000002825 functional assay Methods 0.000 description 4
• DOUHZFSGSXMPIE-UHFFFAOYSA-N hydroxidooxidosulfur(.) Chemical compound [O]SO DOUHZFSGSXMPIE-UHFFFAOYSA-N 0.000 description 4
• 230000005764 inhibitory process Effects 0.000 description 4
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
• AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
• 230000000155 isotopic effect Effects 0.000 description 4
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
• 210000003205 muscle Anatomy 0.000 description 4
• CNRYKDJRCASTBP-UHFFFAOYSA-N n,n-dimethyl-4-naphthalen-1-yl-1,3-oxazol-2-amine Chemical compound O1C(N(C)C)=NC(C=2C3=CC=CC=C3C=CC=2)=C1 CNRYKDJRCASTBP-UHFFFAOYSA-N 0.000 description 4
• VKNGBZDPBUPDGD-UHFFFAOYSA-N n-methyl-4-naphthalen-1-yl-1,3-oxazol-2-amine Chemical compound O1C(NC)=NC(C=2C3=CC=CC=C3C=CC=2)=C1 VKNGBZDPBUPDGD-UHFFFAOYSA-N 0.000 description 4
• WPHGSKGZRAQSGP-UHFFFAOYSA-N norcarane Chemical compound C1CCCC2CC21 WPHGSKGZRAQSGP-UHFFFAOYSA-N 0.000 description 4
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 4
• 229910052763 palladium Inorganic materials 0.000 description 4
• 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 4
• 229960001779 pargyline Drugs 0.000 description 4
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
• 238000001953 recrystallisation Methods 0.000 description 4
• 230000004044 response Effects 0.000 description 4
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
• 239000000741 silica gel Substances 0.000 description 4
• 229910002027 silica gel Inorganic materials 0.000 description 4
• 229910000029 sodium carbonate Inorganic materials 0.000 description 4
• 235000015096 spirit Nutrition 0.000 description 4
• 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 4
• 239000000725 suspension Substances 0.000 description 4
• 125000003396 thiol group Chemical group [H]S* 0.000 description 4
• 210000001519 tissue Anatomy 0.000 description 4
• LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 4
• SKCQROMLEPWCHX-UHFFFAOYSA-N (1-naphthalen-1-yl-1-oxopropan-2-yl) acetate Chemical compound C1=CC=C2C(C(=O)C(OC(C)=O)C)=CC=CC2=C1 SKCQROMLEPWCHX-UHFFFAOYSA-N 0.000 description 3
• LFCAPCQUJCLIPF-UHFFFAOYSA-N (2-amino-5-naphthalen-1-yl-1,3-oxazol-4-yl)methyl acetate Chemical compound N1=C(N)OC(C=2C3=CC=CC=C3C=CC=2)=C1COC(=O)C LFCAPCQUJCLIPF-UHFFFAOYSA-N 0.000 description 3
• RHOYDLWRLGQUBE-UHFFFAOYSA-N 1-hydroxy-1-(2-methoxynaphthalen-1-yl)propan-2-one Chemical compound C1=CC=CC2=C(C(O)C(C)=O)C(OC)=CC=C21 RHOYDLWRLGQUBE-UHFFFAOYSA-N 0.000 description 3
• QFLRYLKUSFJFTK-UHFFFAOYSA-N 1-naphthalen-1-ylpropan-1-one Chemical compound C1=CC=C2C(C(=O)CC)=CC=CC2=C1 QFLRYLKUSFJFTK-UHFFFAOYSA-N 0.000 description 3
• OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
• FYBITYCSBZUHCA-UHFFFAOYSA-N 2-bromo-1-(2-ethoxynaphthalen-1-yl)ethanone Chemical compound C1=CC=CC2=C(C(=O)CBr)C(OCC)=CC=C21 FYBITYCSBZUHCA-UHFFFAOYSA-N 0.000 description 3
• BMUCEDFEWUTYEW-UHFFFAOYSA-N 2-hydroxy-1-(2-methoxynaphthalen-1-yl)propan-1-one Chemical compound C1=CC=CC2=C(C(=O)C(C)O)C(OC)=CC=C21 BMUCEDFEWUTYEW-UHFFFAOYSA-N 0.000 description 3
• TUVYDNPKZDMWOB-UHFFFAOYSA-N 5-(2,3-dihydro-1,4-benzodioxin-5-yl)-1,3-oxazol-2-amine Chemical compound O1C(N)=NC=C1C1=CC=CC2=C1OCCO2 TUVYDNPKZDMWOB-UHFFFAOYSA-N 0.000 description 3
• RXDCFPQWNHVVGJ-UHFFFAOYSA-N 5-(2-methoxynaphthalen-1-yl)-1,3-oxazol-2-amine Chemical compound COC1=CC=C2C=CC=CC2=C1C1=CN=C(N)O1 RXDCFPQWNHVVGJ-UHFFFAOYSA-N 0.000 description 3
• 102000049773 5-HT2A Serotonin Receptor Human genes 0.000 description 3
• 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 description 3
• 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 description 3
• KMJJQZJORLDZLA-UHFFFAOYSA-N 5-naphthalen-1-yl-4-propan-2-yl-1,3-oxazol-2-amine Chemical compound N1=C(N)OC(C=2C3=CC=CC=C3C=CC=2)=C1C(C)C KMJJQZJORLDZLA-UHFFFAOYSA-N 0.000 description 3
• XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 description 3
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
• UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 3
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
• 241000400611 Eucalyptus deanei Species 0.000 description 3
• 101000783617 Homo sapiens 5-hydroxytryptamine receptor 2A Proteins 0.000 description 3
• 101000761348 Homo sapiens 5-hydroxytryptamine receptor 2C Proteins 0.000 description 3
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 3
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
• 239000007983 Tris buffer Substances 0.000 description 3
• POYDEESSZLAILI-UHFFFAOYSA-N [1-(2-methoxynaphthalen-1-yl)-2-oxopropyl] acetate Chemical compound C1=CC=CC2=C(C(OC(C)=O)C(C)=O)C(OC)=CC=C21 POYDEESSZLAILI-UHFFFAOYSA-N 0.000 description 3
• WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
• 239000012346 acetyl chloride Substances 0.000 description 3
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 3
• MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 3
• 150000001543 aryl boronic acids Chemical class 0.000 description 3
• 229960005070 ascorbic acid Drugs 0.000 description 3
• 235000010323 ascorbic acid Nutrition 0.000 description 3
• 239000011668 ascorbic acid Substances 0.000 description 3
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
• 239000001110 calcium chloride Substances 0.000 description 3
• 229910001628 calcium chloride Inorganic materials 0.000 description 3
• 235000011148 calcium chloride Nutrition 0.000 description 3
• 125000002091 cationic group Chemical group 0.000 description 3
• 150000001768 cations Chemical class 0.000 description 3
• 125000004093 cyano group Chemical group *C#N 0.000 description 3
• 238000010494 dissociation reaction Methods 0.000 description 3
• 230000005593 dissociations Effects 0.000 description 3
• 239000002552 dosage form Substances 0.000 description 3
• 239000008103 glucose Substances 0.000 description 3
• 229910052736 halogen Inorganic materials 0.000 description 3
• 150000002367 halogens Chemical class 0.000 description 3
• 125000001841 imino group Chemical group [H]N=* 0.000 description 3
• 238000011534 incubation Methods 0.000 description 3
• PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 3
• FPCCSQOGAWCVBH-UHFFFAOYSA-N ketanserin Chemical compound C1=CC(F)=CC=C1C(=O)C1CCN(CCN2C(C3=CC=CC=C3NC2=O)=O)CC1 FPCCSQOGAWCVBH-UHFFFAOYSA-N 0.000 description 3
• 239000007788 liquid Substances 0.000 description 3
• 238000005567 liquid scintillation counting Methods 0.000 description 3
• JXLHGAXUINNOOW-UHFFFAOYSA-N n-[5-(2-methoxynaphthalen-1-yl)-1,3-oxazol-2-yl]acetamide Chemical compound COC1=CC=C2C=CC=CC2=C1C1=CN=C(NC(C)=O)O1 JXLHGAXUINNOOW-UHFFFAOYSA-N 0.000 description 3
• 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 3
• 125000002971 oxazolyl group Chemical group 0.000 description 3
• 239000000546 pharmaceutical excipient Substances 0.000 description 3
• 230000000144 pharmacologic effect Effects 0.000 description 3
• 239000000843 powder Substances 0.000 description 3
• 239000000047 product Substances 0.000 description 3
• 125000006239 protecting group Chemical group 0.000 description 3
• CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 3
• XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
• 230000000717 retained effect Effects 0.000 description 3
• 239000012047 saturated solution Substances 0.000 description 3
• 239000011734 sodium Substances 0.000 description 3
• 239000011780 sodium chloride Substances 0.000 description 3
• 229940035044 sorbitan monolaurate Drugs 0.000 description 3
• 239000007858 starting material Substances 0.000 description 3
• 230000000638 stimulation Effects 0.000 description 3
• 238000006467 substitution reaction Methods 0.000 description 3
• IWOKCMBOJXYDEE-UHFFFAOYSA-N sulfinylmethane Chemical compound C=S=O IWOKCMBOJXYDEE-UHFFFAOYSA-N 0.000 description 3
• 239000006228 supernatant Substances 0.000 description 3
• QMOMDADTIOMKJH-UHFFFAOYSA-N tert-butyl n-(5-methyl-4-oxo-1,3-oxazol-2-yl)carbamate Chemical compound CC1OC(NC(=O)OC(C)(C)C)=NC1=O QMOMDADTIOMKJH-UHFFFAOYSA-N 0.000 description 3
• 150000003568 thioethers Chemical class 0.000 description 3
• AUHIJZYPLUPNGG-UHFFFAOYSA-N (2-naphthalen-1-yl-2-oxoethyl) acetate Chemical compound C1=CC=C2C(C(=O)COC(=O)C)=CC=CC2=C1 AUHIJZYPLUPNGG-UHFFFAOYSA-N 0.000 description 2
• VAYOSLLFUXYJDT-QZGBZKRISA-N (6ar,9r)-n,n-diethyl-7-(tritritiomethyl)-6,6a,8,9-tetrahydro-4h-indolo[4,3-fg]quinoline-9-carboxamide Chemical compound C1=CC(C2=C[C@H](CN([C@@H]2C2)C([3H])([3H])[3H])C(=O)N(CC)CC)=C3C2=CNC3=C1 VAYOSLLFUXYJDT-QZGBZKRISA-N 0.000 description 2
• 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 2
• ICLYJLBTOGPLMC-KVVVOXFISA-N (z)-octadec-9-enoate;tris(2-hydroxyethyl)azanium Chemical compound OCCN(CCO)CCO.CCCCCCCC\C=C/CCCCCCCC(O)=O ICLYJLBTOGPLMC-KVVVOXFISA-N 0.000 description 2
• CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical compound C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 description 2
• OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 2
• YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 description 2
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
• FRNSEUVCHNZGRF-UHFFFAOYSA-N 1-(1-benzothiophen-4-yl)-2-hydroxyethanone Chemical compound OCC(=O)C1=CC=CC2=C1C=CS2 FRNSEUVCHNZGRF-UHFFFAOYSA-N 0.000 description 2
• FHUCEIUGQFHJJW-UHFFFAOYSA-N 1-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-hydroxyethanone Chemical compound O1CCOC2=CC(C(=O)CO)=CC=C21 FHUCEIUGQFHJJW-UHFFFAOYSA-N 0.000 description 2
• MHRQXUWQKAJKKA-UHFFFAOYSA-N 1-(2-ethoxynaphthalen-1-yl)-2-hydroxyethanone Chemical compound C1=CC=CC2=C(C(=O)CO)C(OCC)=CC=C21 MHRQXUWQKAJKKA-UHFFFAOYSA-N 0.000 description 2
• KFTUKCVZQBDUEY-UHFFFAOYSA-N 1-(2-methylnaphthalen-1-yl)ethanone Chemical compound C1=CC=C2C(C(=O)C)=C(C)C=CC2=C1 KFTUKCVZQBDUEY-UHFFFAOYSA-N 0.000 description 2
• WYCMFCPHWDZHMR-UHFFFAOYSA-N 1-(4,7-dimethyl-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinoline-9-yl)-n,n-dimethylmethanesulfonamide Chemical compound C1=CC(C2CC(CN(C)C2C2)CS(=O)(=O)N(C)C)=C3C2=CN(C)C3=C1 WYCMFCPHWDZHMR-UHFFFAOYSA-N 0.000 description 2
• DQFUZWXIRAWPCJ-UHFFFAOYSA-N 1-(4-fluoronaphthalen-1-yl)-3-methylbutan-1-one Chemical compound C1=CC=C2C(C(=O)CC(C)C)=CC=C(F)C2=C1 DQFUZWXIRAWPCJ-UHFFFAOYSA-N 0.000 description 2
• QGLVUMXWKUNZNQ-UHFFFAOYSA-N 1-(7-bromonaphthalen-1-yl)-2-hydroxyethanone Chemical compound C1=C(Br)C=C2C(C(=O)CO)=CC=CC2=C1 QGLVUMXWKUNZNQ-UHFFFAOYSA-N 0.000 description 2
• IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
• FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
• QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
• 125000006017 1-propenyl group Chemical group 0.000 description 2
• FJRPOHLDJUJARI-UHFFFAOYSA-N 2,3-dihydro-1,2-oxazole Chemical compound C1NOC=C1 FJRPOHLDJUJARI-UHFFFAOYSA-N 0.000 description 2
• ZABMHLDQFJHDSC-UHFFFAOYSA-N 2,3-dihydro-1,3-oxazole Chemical compound C1NC=CO1 ZABMHLDQFJHDSC-UHFFFAOYSA-N 0.000 description 2
• FLNPFFMWAPTGOT-UHFFFAOYSA-N 2,3-dihydro-1h-pyrazole Chemical compound C1NNC=C1.C1NNC=C1 FLNPFFMWAPTGOT-UHFFFAOYSA-N 0.000 description 2
• 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 2
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
• 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 2
• OBQWZCOXZMFLMK-UHFFFAOYSA-N 2-bromo-1-(2-methylnaphthalen-1-yl)ethanone Chemical compound C1=CC=CC2=C(C(=O)CBr)C(C)=CC=C21 OBQWZCOXZMFLMK-UHFFFAOYSA-N 0.000 description 2
• ZNTFNJLHYCRMTB-UHFFFAOYSA-N 2-bromo-1-(2-phenylmethoxynaphthalen-1-yl)ethanone Chemical compound C1=CC2=CC=CC=C2C(C(=O)CBr)=C1OCC1=CC=CC=C1 ZNTFNJLHYCRMTB-UHFFFAOYSA-N 0.000 description 2
• KHLSOOWGQBANDX-UHFFFAOYSA-N 2-bromo-1-(5-bromonaphthalen-1-yl)ethanone Chemical compound C1=CC=C2C(C(=O)CBr)=CC=CC2=C1Br KHLSOOWGQBANDX-UHFFFAOYSA-N 0.000 description 2
• CLMJJCRJUDQLJC-UHFFFAOYSA-N 2-bromo-1-(7-bromonaphthalen-1-yl)ethanone Chemical compound C1=C(Br)C=C2C(C(=O)CBr)=CC=CC2=C1 CLMJJCRJUDQLJC-UHFFFAOYSA-N 0.000 description 2
• ORPPMNLQDHEBLB-UHFFFAOYSA-N 2-hydroxy-1-(2-methoxynaphthalen-1-yl)ethanone Chemical compound C1=CC=CC2=C(C(=O)CO)C(OC)=CC=C21 ORPPMNLQDHEBLB-UHFFFAOYSA-N 0.000 description 2
• LIAKUKLBPAXANU-UHFFFAOYSA-N 2-hydroxy-1-(2-methylnaphthalen-1-yl)ethanone Chemical compound C1=CC=CC2=C(C(=O)CO)C(C)=CC=C21 LIAKUKLBPAXANU-UHFFFAOYSA-N 0.000 description 2
• RGJRJBNJZGSYQW-UHFFFAOYSA-N 2-hydroxy-1-(2-phenylmethoxynaphthalen-1-yl)ethanone Chemical compound C1=CC2=CC=CC=C2C(C(=O)CO)=C1OCC1=CC=CC=C1 RGJRJBNJZGSYQW-UHFFFAOYSA-N 0.000 description 2
• DCQNLWSWZGITPK-UHFFFAOYSA-N 2-hydroxy-1-(3-methyl-1-benzothiophen-2-yl)ethanone Chemical compound C1=CC=C2C(C)=C(C(=O)CO)SC2=C1 DCQNLWSWZGITPK-UHFFFAOYSA-N 0.000 description 2
• QFLYHUTYXNMXIU-UHFFFAOYSA-N 2-hydroxy-1-(4-methoxynaphthalen-1-yl)ethanone Chemical compound C1=CC=C2C(OC)=CC=C(C(=O)CO)C2=C1 QFLYHUTYXNMXIU-UHFFFAOYSA-N 0.000 description 2
• BEIIYTIDGSZGDA-UHFFFAOYSA-N 2-hydroxy-1-naphthalen-1-ylethanone Chemical compound C1=CC=C2C(C(=O)CO)=CC=CC2=C1 BEIIYTIDGSZGDA-UHFFFAOYSA-N 0.000 description 2
• HMYNGQYVXBPOEN-UHFFFAOYSA-N 2-hydroxy-1-naphthalen-2-ylethanone Chemical compound C1=CC=CC2=CC(C(=O)CO)=CC=C21 HMYNGQYVXBPOEN-UHFFFAOYSA-N 0.000 description 2
• VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 description 2
• RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 2
• QMEQBOSUJUOXMX-UHFFFAOYSA-N 2h-oxadiazine Chemical compound N1OC=CC=N1 QMEQBOSUJUOXMX-UHFFFAOYSA-N 0.000 description 2
• BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 2
• BOLMDIXLULGTBD-UHFFFAOYSA-N 3,4-dihydro-2h-oxazine Chemical compound C1CC=CON1 BOLMDIXLULGTBD-UHFFFAOYSA-N 0.000 description 2
• VXIKDBJPBRMXBP-UHFFFAOYSA-N 3H-pyrrole Chemical compound C1C=CN=C1 VXIKDBJPBRMXBP-UHFFFAOYSA-N 0.000 description 2
• RELAJOWOFXGXHI-UHFFFAOYSA-N 3h-oxathiole Chemical compound C1SOC=C1 RELAJOWOFXGXHI-UHFFFAOYSA-N 0.000 description 2
• OGAXVVQAVJJILM-UHFFFAOYSA-N 4-bromo-1,3-oxazol-2-amine Chemical compound NC1=NC(Br)=CO1 OGAXVVQAVJJILM-UHFFFAOYSA-N 0.000 description 2
• 229940116892 5 Hydroxytryptamine 2B receptor antagonist Drugs 0.000 description 2
• 101710138091 5-hydroxytryptamine receptor 2A Proteins 0.000 description 2
• 102100036321 5-hydroxytryptamine receptor 2A Human genes 0.000 description 2
• NJBMMMJOXRZENQ-UHFFFAOYSA-N 6H-pyrrolo[2,3-f]quinoline Chemical compound c1cc2ccc3[nH]cccc3c2n1 NJBMMMJOXRZENQ-UHFFFAOYSA-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
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
• GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical class 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 2
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
• 241000557626 Corvus corax Species 0.000 description 2
• PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 2
• LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 2
• FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical class OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
• BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 2
• 102000013138 Drug Receptors Human genes 0.000 description 2
• 108010065556 Drug Receptors Proteins 0.000 description 2
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
• 239000007995 HEPES buffer Substances 0.000 description 2
• 101150104779 HTR2A gene Proteins 0.000 description 2
• 101150013372 Htr2c gene Proteins 0.000 description 2
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
• WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 2
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical class 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 2
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
• 229930195725 Mannitol Natural products 0.000 description 2
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
• UEQUQVLFIPOEMF-UHFFFAOYSA-N Mianserin Chemical compound C1C2=CC=CC=C2N2CCN(C)CC2C2=CC=CC=C21 UEQUQVLFIPOEMF-UHFFFAOYSA-N 0.000 description 2
• JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
• WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 2
• 102100035591 POU domain, class 2, transcription factor 2 Human genes 0.000 description 2
• 101710084411 POU domain, class 2, transcription factor 2 Proteins 0.000 description 2
• 229930182555 Penicillin Natural products 0.000 description 2
• 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 2
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
• GNSXDDLDAGAXTL-UHFFFAOYSA-N S1OCCCC1.O1SCCCC1 Chemical compound S1OCCCC1.O1SCCCC1 GNSXDDLDAGAXTL-UHFFFAOYSA-N 0.000 description 2
• 229920002472 Starch Polymers 0.000 description 2
• CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
• 229930006000 Sucrose Natural products 0.000 description 2
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
• NKGJQEGXSBODRR-UHFFFAOYSA-N [1-(4-fluoronaphthalen-1-yl)-3-methyl-1-oxobutan-2-yl] acetate Chemical compound C1=CC=C2C(C(=O)C(OC(C)=O)C(C)C)=CC=C(F)C2=C1 NKGJQEGXSBODRR-UHFFFAOYSA-N 0.000 description 2
• MRMDUINMTIKQBO-UHFFFAOYSA-N [2-(2-methylnaphthalen-1-yl)-2-oxoethyl] acetate Chemical compound C1=CC=C2C(C(=O)COC(=O)C)=C(C)C=CC2=C1 MRMDUINMTIKQBO-UHFFFAOYSA-N 0.000 description 2
• NBUVBYTWWCLTKC-UHFFFAOYSA-N [2-(4-methoxynaphthalen-1-yl)-2-oxoethyl] acetate Chemical compound C1=CC=C2C(OC)=CC=C(C(=O)COC(C)=O)C2=C1 NBUVBYTWWCLTKC-UHFFFAOYSA-N 0.000 description 2
• HPYUPWXAKWZYPG-UHFFFAOYSA-N [2-(5-bromonaphthalen-1-yl)-2-oxoethyl] acetate Chemical compound C1=CC=C2C(C(=O)COC(=O)C)=CC=CC2=C1Br HPYUPWXAKWZYPG-UHFFFAOYSA-N 0.000 description 2
• ZGEYKZCNFQNUMY-UHFFFAOYSA-N [2-oxo-2-(2-phenylmethoxynaphthalen-1-yl)ethyl] acetate Chemical compound C1=CC2=CC=CC=C2C(C(=O)COC(=O)C)=C1OCC1=CC=CC=C1 ZGEYKZCNFQNUMY-UHFFFAOYSA-N 0.000 description 2
• ZFYDTMFWVYECGH-UHFFFAOYSA-N [5-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]-1,3-oxazol-4-yl] trifluoromethanesulfonate Chemical compound CC=1OC(NC(=O)OC(C)(C)C)=NC=1OS(=O)(=O)C(F)(F)F ZFYDTMFWVYECGH-UHFFFAOYSA-N 0.000 description 2
• GXVKHKJETWAWRR-UHFFFAOYSA-N a805143 Chemical compound C1CCNC1.C1CCNC1 GXVKHKJETWAWRR-UHFFFAOYSA-N 0.000 description 2
• CWRYPZZKDGJXCA-UHFFFAOYSA-N acenaphthene Chemical compound C1=CC(CC2)=C3C2=CC=CC3=C1 CWRYPZZKDGJXCA-UHFFFAOYSA-N 0.000 description 2
• QOMNQGZXFYNBNG-UHFFFAOYSA-N acetyloxymethyl 2-[2-[2-[5-[3-(acetyloxymethoxy)-2,7-difluoro-6-oxoxanthen-9-yl]-2-[bis[2-(acetyloxymethoxy)-2-oxoethyl]amino]phenoxy]ethoxy]-n-[2-(acetyloxymethoxy)-2-oxoethyl]-4-methylanilino]acetate Chemical compound CC(=O)OCOC(=O)CN(CC(=O)OCOC(C)=O)C1=CC=C(C)C=C1OCCOC1=CC(C2=C3C=C(F)C(=O)C=C3OC3=CC(OCOC(C)=O)=C(F)C=C32)=CC=C1N(CC(=O)OCOC(C)=O)CC(=O)OCOC(C)=O QOMNQGZXFYNBNG-UHFFFAOYSA-N 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
• 125000002252 acyl group Chemical group 0.000 description 2
• 125000004423 acyloxy group Chemical group 0.000 description 2
• ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
• 150000001299 aldehydes Chemical class 0.000 description 2
• 150000004983 alkyl aryl ketones Chemical class 0.000 description 2
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
• VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
• APKFDSVGJQXUKY-INPOYWNPSA-N amphotericin B Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-INPOYWNPSA-N 0.000 description 2
• 238000004458 analytical method Methods 0.000 description 2
• 238000013459 approach Methods 0.000 description 2
• XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 2
• 239000002585 base Substances 0.000 description 2
• IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
• LUFPJJNWMYZRQE-UHFFFAOYSA-N benzylsulfanylmethylbenzene Chemical compound C=1C=CC=CC=1CSCC1=CC=CC=C1 LUFPJJNWMYZRQE-UHFFFAOYSA-N 0.000 description 2
• 230000000903 blocking effect Effects 0.000 description 2
• HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
• 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 2
• CRPUJAZIXJMDBK-UHFFFAOYSA-N camphene Chemical compound C1CC2C(=C)C(C)(C)C1C2 CRPUJAZIXJMDBK-UHFFFAOYSA-N 0.000 description 2
• BWRHOYDPVJPXMF-UHFFFAOYSA-N carane Chemical compound C1C(C)CCC2C(C)(C)C12 BWRHOYDPVJPXMF-UHFFFAOYSA-N 0.000 description 2
• 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 2
• 125000002837 carbocyclic group Chemical group 0.000 description 2
• 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
• SKOLWUPSYHWYAM-UHFFFAOYSA-N carbonodithioic O,S-acid Chemical compound SC(S)=O SKOLWUPSYHWYAM-UHFFFAOYSA-N 0.000 description 2
• 150000007942 carboxylates Chemical class 0.000 description 2
• 239000003054 catalyst Substances 0.000 description 2
• 238000004587 chromatography analysis Methods 0.000 description 2
• WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 2
• 238000009833 condensation Methods 0.000 description 2
• 230000005494 condensation Effects 0.000 description 2
• 238000005859 coupling reaction Methods 0.000 description 2
• HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
• LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
• 239000008121 dextrose Substances 0.000 description 2
• TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
• IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-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
• 125000002228 disulfide group Chemical group 0.000 description 2
• 239000003995 emulsifying agent Substances 0.000 description 2
• 125000002587 enol group Chemical group 0.000 description 2
• CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 2
• IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
• RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 2
• 239000006260 foam Substances 0.000 description 2
• 239000012909 foetal bovine serum Substances 0.000 description 2
• FATAVLOOLIRUNA-UHFFFAOYSA-N formylmethyl Chemical group [CH2]C=O FATAVLOOLIRUNA-UHFFFAOYSA-N 0.000 description 2
• 235000001727 glucose Nutrition 0.000 description 2
• UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 2
• 150000002391 heterocyclic compounds Chemical class 0.000 description 2
• 125000006038 hexenyl group Chemical group 0.000 description 2
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
• 238000000265 homogenisation Methods 0.000 description 2
• MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 2
• 150000002466 imines Chemical class 0.000 description 2
• 238000000338 in vitro Methods 0.000 description 2
• 238000002347 injection Methods 0.000 description 2
• 239000007924 injection Substances 0.000 description 2
• 230000003993 interaction Effects 0.000 description 2
• 239000000543 intermediate Substances 0.000 description 2
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
• 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 2
• 150000002576 ketones Chemical class 0.000 description 2
• 239000008101 lactose Chemical class 0.000 description 2
• 239000011777 magnesium Substances 0.000 description 2
• 229910052749 magnesium Inorganic materials 0.000 description 2
• ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 2
• 239000001095 magnesium carbonate Substances 0.000 description 2
• 229910000021 magnesium carbonate Inorganic materials 0.000 description 2
• 235000019359 magnesium stearate Nutrition 0.000 description 2
• 239000000594 mannitol Substances 0.000 description 2
• 235000010355 mannitol Nutrition 0.000 description 2
• 230000000873 masking effect Effects 0.000 description 2
• 239000000463 material Substances 0.000 description 2
• MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 2
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
• 229960003955 mianserin Drugs 0.000 description 2
• 210000004877 mucosa Anatomy 0.000 description 2
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
• 150000002825 nitriles Chemical class 0.000 description 2
• 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 description 2
• 125000000018 nitroso group Chemical group N(=O)* 0.000 description 2
• 230000009871 nonspecific binding Effects 0.000 description 2
• 150000002891 organic anions Chemical class 0.000 description 2
• AZHVQJLDOFKHPZ-UHFFFAOYSA-N oxathiazine Chemical compound O1SN=CC=C1 AZHVQJLDOFKHPZ-UHFFFAOYSA-N 0.000 description 2
• 239000006179 pH buffering agent Substances 0.000 description 2
• 239000008188 pellet Substances 0.000 description 2
• 229940049954 penicillin Drugs 0.000 description 2
• 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 2
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
• YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 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
• YBYRMVIVWMBXKQ-UHFFFAOYSA-N phenylmethanesulfonyl fluoride Chemical compound FS(=O)(=O)CC1=CC=CC=C1 YBYRMVIVWMBXKQ-UHFFFAOYSA-N 0.000 description 2
• XOKSLPVRUOBDEW-UHFFFAOYSA-N pinane Chemical compound CC1CCC2C(C)(C)C1C2 XOKSLPVRUOBDEW-UHFFFAOYSA-N 0.000 description 2
• SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
• UBRJWPDONDYLLX-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1.C1CNNC1 UBRJWPDONDYLLX-UHFFFAOYSA-N 0.000 description 2
• ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 2
• 238000001525 receptor binding assay Methods 0.000 description 2
• 229910052708 sodium Inorganic materials 0.000 description 2
• ILJOYZVVZZFIKA-UHFFFAOYSA-M sodium;1,1-dioxo-1,2-benzothiazol-3-olate;hydrate Chemical compound O.[Na+].C1=CC=C2C(=O)[N-]S(=O)(=O)C2=C1 ILJOYZVVZZFIKA-UHFFFAOYSA-M 0.000 description 2
• DCQXTYAFFMSNNH-UHFFFAOYSA-M sodium;2-[bis(2-hydroxyethyl)amino]ethanol;acetate Chemical compound [Na+].CC([O-])=O.OCCN(CCO)CCO DCQXTYAFFMSNNH-UHFFFAOYSA-M 0.000 description 2
• 238000001228 spectrum Methods 0.000 description 2
• 239000008107 starch Substances 0.000 description 2
• 235000019698 starch Nutrition 0.000 description 2
• 229960005322 streptomycin Drugs 0.000 description 2
• 239000005720 sucrose Substances 0.000 description 2
• 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 2
• 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 2
• 150000003457 sulfones Chemical class 0.000 description 2
• 239000000454 talc Substances 0.000 description 2
• 235000012222 talc Nutrition 0.000 description 2
• 229910052623 talc Inorganic materials 0.000 description 2
• DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 2
• KHVCOYGKHDJPBZ-WDCZJNDASA-N tetrahydrooxazine Chemical compound OC[C@H]1ONC[C@@H](O)[C@@H]1O KHVCOYGKHDJPBZ-WDCZJNDASA-N 0.000 description 2
• 230000001225 therapeutic effect Effects 0.000 description 2
• CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 2
• BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 2
• GCTNBVHDRFKLLK-UHFFFAOYSA-N thujane Chemical compound CC1CCC2(C(C)C)C1C2 GCTNBVHDRFKLLK-UHFFFAOYSA-N 0.000 description 2
• 229940117013 triethanolamine oleate Drugs 0.000 description 2
• WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 2
• 229920002554 vinyl polymer Polymers 0.000 description 2
• 239000003039 volatile agent Substances 0.000 description 2
• 238000009736 wetting Methods 0.000 description 2
• 239000000080 wetting agent Substances 0.000 description 2
• KLUFIJCKPYMWHW-UHFFFAOYSA-N (1-naphthalen-1-yl-2-oxopropyl) acetate Chemical compound C1=CC=C2C(C(C(C)=O)OC(=O)C)=CC=CC2=C1 KLUFIJCKPYMWHW-UHFFFAOYSA-N 0.000 description 1
• VSNKQFOXXBIKEH-UHFFFAOYSA-N (2-naphthalen-2-yl-2-oxoethyl) acetate Chemical compound C1=CC=CC2=CC(C(=O)COC(=O)C)=CC=C21 VSNKQFOXXBIKEH-UHFFFAOYSA-N 0.000 description 1
• FFVKPRCLDRQJIP-UHFFFAOYSA-N (3-methyl-1-naphthalen-1-yl-1-oxobutan-2-yl) acetate Chemical compound C1=CC=C2C(C(=O)C(OC(C)=O)C(C)C)=CC=CC2=C1 FFVKPRCLDRQJIP-UHFFFAOYSA-N 0.000 description 1
• 125000006701 (C1-C7) alkyl group Chemical group 0.000 description 1
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 description 1
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 1
• IDFPQEHZYBXIFO-GFCCVEGCSA-N (R)-(4-fluoro-2-propylphenyl)-(1H-imidazol-2-yl)methanol Chemical compound CCCc1cc(F)ccc1[C@@H](O)c1ncc[nH]1 IDFPQEHZYBXIFO-GFCCVEGCSA-N 0.000 description 1
• YBBLOADPFWKNGS-UHFFFAOYSA-N 1,1-dimethylurea Chemical compound CN(C)C(N)=O YBBLOADPFWKNGS-UHFFFAOYSA-N 0.000 description 1
• FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 1
• KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 1
• BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
• FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 description 1
• BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
• WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
• RAVKDBINTWOXDN-UHFFFAOYSA-N 1,5-benzoxazepine Chemical compound O1C=CC=NC2=CC=CC=C12 RAVKDBINTWOXDN-UHFFFAOYSA-N 0.000 description 1
• VMLKTERJLVWEJJ-UHFFFAOYSA-N 1,5-naphthyridine Chemical compound C1=CC=NC2=CC=CN=C21 VMLKTERJLVWEJJ-UHFFFAOYSA-N 0.000 description 1
• FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
• XZJLLWWNPKTWHQ-UHFFFAOYSA-N 1-(1-benzothiophen-4-yl)-2-bromoethanone Chemical compound BrCC(=O)C1=CC=CC2=C1C=CS2 XZJLLWWNPKTWHQ-UHFFFAOYSA-N 0.000 description 1
• URLFUQDJJLGFOD-UHFFFAOYSA-N 1-(1-benzothiophen-4-yl)ethanone Chemical compound CC(=O)C1=CC=CC2=C1C=CS2 URLFUQDJJLGFOD-UHFFFAOYSA-N 0.000 description 1
• UXQCCXLEKIFOEZ-UHFFFAOYSA-N 1-(2-ethoxynaphthalen-1-yl)ethanone Chemical compound C1=CC=CC2=C(C(C)=O)C(OCC)=CC=C21 UXQCCXLEKIFOEZ-UHFFFAOYSA-N 0.000 description 1
• JTPFWUSNQJOLER-UHFFFAOYSA-N 1-(2-methoxynaphthalen-1-yl)propan-1-one Chemical compound C1=CC=C2C(C(=O)CC)=C(OC)C=CC2=C1 JTPFWUSNQJOLER-UHFFFAOYSA-N 0.000 description 1
• NUIZDNACBJIQKM-UHFFFAOYSA-N 1-(2-phenylmethoxynaphthalen-1-yl)ethanone Chemical compound C1=CC2=CC=CC=C2C(C(=O)C)=C1OCC1=CC=CC=C1 NUIZDNACBJIQKM-UHFFFAOYSA-N 0.000 description 1
• UMSVGXXUTBJKCF-UHFFFAOYSA-N 1-(4-fluoronaphthalen-1-yl)-2-hydroxy-3-methylbutan-1-one Chemical compound C1=CC=C2C(C(=O)C(O)C(C)C)=CC=C(F)C2=C1 UMSVGXXUTBJKCF-UHFFFAOYSA-N 0.000 description 1
• ILWVQZNFIPLUJE-UHFFFAOYSA-N 1-(5-bromonaphthalen-1-yl)-2-hydroxyethanone Chemical compound C1=CC=C2C(C(=O)CO)=CC=CC2=C1Br ILWVQZNFIPLUJE-UHFFFAOYSA-N 0.000 description 1
• CKVLRTAJCSSPCT-UHFFFAOYSA-N 1-(5-bromonaphthalen-1-yl)ethanone Chemical compound C1=CC=C2C(C(=O)C)=CC=CC2=C1Br CKVLRTAJCSSPCT-UHFFFAOYSA-N 0.000 description 1
• XPIBNCGHRJCREA-UHFFFAOYSA-N 1-(7-bromonaphthalen-1-yl)ethanone Chemical compound C1=C(Br)C=C2C(C(=O)C)=CC=CC2=C1 XPIBNCGHRJCREA-UHFFFAOYSA-N 0.000 description 1
• TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-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
• DQFQCHIDRBIESA-UHFFFAOYSA-N 1-benzazepine Chemical compound N1C=CC=CC2=CC=CC=C12 DQFQCHIDRBIESA-UHFFFAOYSA-N 0.000 description 1
• UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
• CWLKTJOTWITYSI-UHFFFAOYSA-N 1-fluoronaphthalene Chemical compound C1=CC=C2C(F)=CC=CC2=C1 CWLKTJOTWITYSI-UHFFFAOYSA-N 0.000 description 1
• WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-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
• HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-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
• MFJCPDOGFAYSTF-UHFFFAOYSA-N 1H-isochromene Chemical compound C1=CC=C2COC=CC2=C1 MFJCPDOGFAYSTF-UHFFFAOYSA-N 0.000 description 1
• AAQTWLBJPNLKHT-UHFFFAOYSA-N 1H-perimidine Chemical compound N1C=NC2=CC=CC3=CC=CC1=C32 AAQTWLBJPNLKHT-UHFFFAOYSA-N 0.000 description 1
• AWBOSXFRPFZLOP-UHFFFAOYSA-N 2,1,3-benzoxadiazole Chemical compound C1=CC=CC2=NON=C21 AWBOSXFRPFZLOP-UHFFFAOYSA-N 0.000 description 1
• MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 1
• ALMAAWJZOBVMNK-UHFFFAOYSA-N 2,2-dibromo-1-(2-ethoxynaphthalen-1-yl)ethanone Chemical compound C1=CC=CC2=C(C(=O)C(Br)Br)C(OCC)=CC=C21 ALMAAWJZOBVMNK-UHFFFAOYSA-N 0.000 description 1
• JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 description 1
• GPWNWKWQOLEVEQ-UHFFFAOYSA-N 2,4-diaminopyrimidine-5-carbaldehyde Chemical compound NC1=NC=C(C=O)C(N)=N1 GPWNWKWQOLEVEQ-UHFFFAOYSA-N 0.000 description 1
• GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
• WNWAWYJJSALSTP-UHFFFAOYSA-N 2-amino-5-methyl-1,3-oxazol-4-one Chemical compound CC1OC(N)=NC1=O WNWAWYJJSALSTP-UHFFFAOYSA-N 0.000 description 1
• UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 description 1
• CSSHRKYOZTZFCX-UHFFFAOYSA-N 2-bromo-1-(2,3-dihydro-1,4-benzodioxin-6-yl)ethanone Chemical compound O1CCOC2=CC(C(=O)CBr)=CC=C21 CSSHRKYOZTZFCX-UHFFFAOYSA-N 0.000 description 1
• IIHGACKVHIKPQE-UHFFFAOYSA-N 2-bromo-1-(2-methoxynaphthalen-1-yl)propan-1-one Chemical compound C1=CC=CC2=C(C(=O)C(C)Br)C(OC)=CC=C21 IIHGACKVHIKPQE-UHFFFAOYSA-N 0.000 description 1
• RSZBQMBOXPUDSN-UHFFFAOYSA-N 2-bromo-1-(2-methoxynaphthalen-1-yl)propan-1-one Chemical compound C1=CC=CC2=C(C(=O)C(C)Br)C(OC)=CC=C21.C1=CC=CC2=C(C(=O)C(C)Br)C(OC)=CC=C21 RSZBQMBOXPUDSN-UHFFFAOYSA-N 0.000 description 1
• PIQSJBQPXDKSHF-UHFFFAOYSA-N 2-bromo-1-(3-methyl-1-benzothiophen-2-yl)ethanone Chemical compound C1=CC=C2C(C)=C(C(=O)CBr)SC2=C1 PIQSJBQPXDKSHF-UHFFFAOYSA-N 0.000 description 1
• FNSMSMKIEFGKAB-UHFFFAOYSA-N 2-bromo-1-(4-fluoronaphthalen-1-yl)-3-methylbutan-1-one Chemical compound C1=CC=C2C(C(=O)C(Br)C(C)C)=CC=C(F)C2=C1 FNSMSMKIEFGKAB-UHFFFAOYSA-N 0.000 description 1
• NHSCJKKYQSHRIB-UHFFFAOYSA-N 2-bromo-1-(4-methoxynaphthalen-1-yl)ethanone Chemical compound C1=CC=C2C(OC)=CC=C(C(=O)CBr)C2=C1 NHSCJKKYQSHRIB-UHFFFAOYSA-N 0.000 description 1
• OQLCVXVVASQZLX-UHFFFAOYSA-N 2-bromo-1-naphthalen-1-ylethanone Chemical compound C1=CC=C2C(C(=O)CBr)=CC=CC2=C1 OQLCVXVVASQZLX-UHFFFAOYSA-N 0.000 description 1
• RLYZHNJGNGTNJO-UHFFFAOYSA-N 2-bromo-3-methyl-1-naphthalen-1-ylbutan-1-one Chemical compound C1=CC=C2C(C(=O)C(Br)C(C)C)=CC=CC2=C1 RLYZHNJGNGTNJO-UHFFFAOYSA-N 0.000 description 1
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
• KDOZGLZAJDIPHO-UHFFFAOYSA-N 2-hydroxy-1-(1-methoxynaphthalen-2-yl)ethanone Chemical compound C1=CC=C2C(OC)=C(C(=O)CO)C=CC2=C1 KDOZGLZAJDIPHO-UHFFFAOYSA-N 0.000 description 1
• NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 1
• UPHOPMSGKZNELG-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=C(O)C=CC2=C1 UPHOPMSGKZNELG-UHFFFAOYSA-N 0.000 description 1
• XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 1
• 229940080296 2-naphthalenesulfonate Drugs 0.000 description 1
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
• BQTJMKIHKULPCZ-UHFFFAOYSA-N 2H-indene Chemical compound C1=CC=CC2=CCC=C21 BQTJMKIHKULPCZ-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
• MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
• CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 description 1
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
• HJCQECPIMVMCSN-UHFFFAOYSA-N 3-methyl-1-naphthalen-1-ylbutan-1-one Chemical compound C1=CC=C2C(C(=O)CC(C)C)=CC=CC2=C1 HJCQECPIMVMCSN-UHFFFAOYSA-N 0.000 description 1
• ISULZYQDGYXDFW-UHFFFAOYSA-N 3-methylbutanoyl chloride Chemical compound CC(C)CC(Cl)=O ISULZYQDGYXDFW-UHFFFAOYSA-N 0.000 description 1
• ZBWXZZIIMVVCNZ-UHFFFAOYSA-N 4,5-dihydroacephenanthrylene Chemical compound C1=CC(CC2)=C3C2=CC2=CC=CC=C2C3=C1 ZBWXZZIIMVVCNZ-UHFFFAOYSA-N 0.000 description 1
• DFUZSIZHYGJRES-UHFFFAOYSA-N 4-(2-ethoxynaphthalen-1-yl)-1,3-oxazol-2-amine Chemical compound CCOC1=CC=C2C=CC=CC2=C1C1=COC(N)=N1 DFUZSIZHYGJRES-UHFFFAOYSA-N 0.000 description 1
• CWCZGFGPXQWRIR-UHFFFAOYSA-N 4-(2-methylnaphthalen-1-yl)-1,3-oxazol-2-amine Chemical compound CC1=CC=C2C=CC=CC2=C1C1=COC(N)=N1 CWCZGFGPXQWRIR-UHFFFAOYSA-N 0.000 description 1
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 1
• QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
• QPBSEYFVZDMBFW-UHFFFAOYSA-N 4-bromo-1-benzothiophene Chemical compound BrC1=CC=CC2=C1C=CS2 QPBSEYFVZDMBFW-UHFFFAOYSA-N 0.000 description 1
• MBVFRSJFKMJRHA-UHFFFAOYSA-N 4-fluoro-1-benzofuran-7-carbaldehyde Chemical compound FC1=CC=C(C=O)C2=C1C=CO2 MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 description 1
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
• 125000006418 4-methylphenylsulfonyl group Chemical group 0.000 description 1
• GDRVFDDBLLKWRI-UHFFFAOYSA-N 4H-quinolizine Chemical compound C1=CC=CN2CC=CC=C21 GDRVFDDBLLKWRI-UHFFFAOYSA-N 0.000 description 1
• JXSKADGZTIBPIO-UHFFFAOYSA-N 5-(2,3-dihydro-1,4-benzodioxin-6-yl)-1,3-oxazol-2-amine Chemical compound O1C(N)=NC=C1C1=CC=C(OCCO2)C2=C1 JXSKADGZTIBPIO-UHFFFAOYSA-N 0.000 description 1
• BBEQQKBWUHCIOU-UHFFFAOYSA-N 5-(dimethylamino)-1-naphthalenesulfonic acid(dansyl acid) Chemical compound C1=CC=C2C(N(C)C)=CC=CC2=C1S(O)(=O)=O BBEQQKBWUHCIOU-UHFFFAOYSA-N 0.000 description 1
• DJFJOSNHIRTFGQ-UHFFFAOYSA-N 5-bromo-1,3-oxazol-2-amine Chemical group NC1=NC=C(Br)O1 DJFJOSNHIRTFGQ-UHFFFAOYSA-N 0.000 description 1
• 101710138092 5-hydroxytryptamine receptor 2B Proteins 0.000 description 1
• 102100024956 5-hydroxytryptamine receptor 2B Human genes 0.000 description 1
• PQJUJGAVDBINPI-UHFFFAOYSA-N 9H-thioxanthene Chemical compound C1=CC=C2CC3=CC=CC=C3SC2=C1 PQJUJGAVDBINPI-UHFFFAOYSA-N 0.000 description 1
• GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 1
• 239000005964 Acibenzolar-S-methyl Substances 0.000 description 1
• GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 1
• 229930024421 Adenine Natural products 0.000 description 1
• 208000007848 Alcoholism Diseases 0.000 description 1
• 208000000103 Anorexia Nervosa Diseases 0.000 description 1
• 208000019901 Anxiety disease Diseases 0.000 description 1
• 101100188555 Arabidopsis thaliana OCT6 gene Proteins 0.000 description 1
• 239000004475 Arginine Substances 0.000 description 1
• NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
• 206010069632 Bladder dysfunction Diseases 0.000 description 1
• 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
• COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
• ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
• 125000003358 C2-C20 alkenyl group Chemical group 0.000 description 1
• 101100294106 Caenorhabditis elegans nhr-3 gene Proteins 0.000 description 1
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
• 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
• 238000005361 D2 NMR spectroscopy Methods 0.000 description 1
• XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
• XTAHYROJKCXMOF-UHFFFAOYSA-N Dihydroaceanthrylene Chemical compound C1=CC=C2C(CCC3=CC=C4)=C3C4=CC2=C1 XTAHYROJKCXMOF-UHFFFAOYSA-N 0.000 description 1
• BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
• 239000003109 Disodium ethylene diamine tetraacetate Substances 0.000 description 1
• SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
• 206010013935 Dysmenorrhoea Diseases 0.000 description 1
• OVBJJZOQPCKUOR-UHFFFAOYSA-L EDTA disodium salt dihydrate Chemical compound O.O.[Na+].[Na+].[O-]C(=O)C[NH+](CC([O-])=O)CC[NH+](CC([O-])=O)CC([O-])=O OVBJJZOQPCKUOR-UHFFFAOYSA-L 0.000 description 1
• 201000009273 Endometriosis Diseases 0.000 description 1
• JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
• YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 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
• 244000166102 Eucalyptus leucoxylon Species 0.000 description 1
• 235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 1
• 239000001263 FEMA 3042 Substances 0.000 description 1
• 206010016654 Fibrosis Diseases 0.000 description 1
• 238000003747 Grignard reaction Methods 0.000 description 1
• 239000012981 Hank's balanced salt solution Substances 0.000 description 1
• 101000761319 Homo sapiens 5-hydroxytryptamine receptor 2B Proteins 0.000 description 1
• LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 1
• 206010020772 Hypertension Diseases 0.000 description 1
• 206010021639 Incontinence Diseases 0.000 description 1
• 239000007836 KH2PO4 Substances 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
• JLVHTNZNKOSCNB-YSVLISHTSA-N Mesulergine Chemical compound C1=CC([C@H]2C[C@@H](CN(C)[C@@H]2C2)NS(=O)(=O)N(C)C)=C3C2=CN(C)C3=C1 JLVHTNZNKOSCNB-YSVLISHTSA-N 0.000 description 1
• 241001465754 Metazoa Species 0.000 description 1
• AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
• 208000019695 Migraine disease Diseases 0.000 description 1
• MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
• 229910005883 NiSi Inorganic materials 0.000 description 1
• VYEAHXRPWKOEMY-UHFFFAOYSA-N O-(9H-fluoren-9-ylmethyl)hydroxylamine Chemical compound C1=CC=C2C(CON)C3=CC=CC=C3C2=C1 VYEAHXRPWKOEMY-UHFFFAOYSA-N 0.000 description 1
• BHVRCUAHXVLSNX-UHFFFAOYSA-N O-[(4,5-dimethoxy-2-nitrophenyl)methyl]hydroxylamine Chemical compound COC1=CC(CON)=C([N+]([O-])=O)C=C1OC BHVRCUAHXVLSNX-UHFFFAOYSA-N 0.000 description 1
• 208000021384 Obsessive-Compulsive disease Diseases 0.000 description 1
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
• 208000002193 Pain Diseases 0.000 description 1
• LRBQNJMCXXYXIU-PPKXGCFTSA-N Penta-digallate-beta-D-glucose Natural products OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-PPKXGCFTSA-N 0.000 description 1
• BELBBZDIHDAJOR-UHFFFAOYSA-N Phenolsulfonephthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2S(=O)(=O)O1 BELBBZDIHDAJOR-UHFFFAOYSA-N 0.000 description 1
• 229920002873 Polyethylenimine Polymers 0.000 description 1
• PXRCIOIWVGAZEP-UHFFFAOYSA-N Primaeres Camphenhydrat Natural products C1CC2C(O)(C)C(C)(C)C1C2 PXRCIOIWVGAZEP-UHFFFAOYSA-N 0.000 description 1
• 229910006069 SO3H Inorganic materials 0.000 description 1
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
• UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
• YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 description 1
• 241001061127 Thione Species 0.000 description 1
• ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
• 102000004142 Trypsin Human genes 0.000 description 1
• 108090000631 Trypsin Proteins 0.000 description 1
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-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
• CYGPFGIPDNWNEO-UHFFFAOYSA-N [1-(2-methoxynaphthalen-1-yl)-1-oxopropan-2-yl] acetate Chemical compound C1=CC=CC2=C(C(=O)C(C)OC(C)=O)C(OC)=CC=C21 CYGPFGIPDNWNEO-UHFFFAOYSA-N 0.000 description 1
• HQPQYAZFZBGKSC-UHFFFAOYSA-N [2-(1-benzothiophen-4-yl)-2-oxoethyl] acetate Chemical compound CC(=O)OCC(=O)C1=CC=CC2=C1C=CS2 HQPQYAZFZBGKSC-UHFFFAOYSA-N 0.000 description 1
• YCBWAHOEGDXKPP-UHFFFAOYSA-N [2-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-oxoethyl] acetate Chemical compound O1CCOC2=CC(C(=O)COC(=O)C)=CC=C21 YCBWAHOEGDXKPP-UHFFFAOYSA-N 0.000 description 1
• IBFXZGKNUYQYGX-UHFFFAOYSA-N [2-(2-ethoxynaphthalen-1-yl)-2-oxoethyl] acetate Chemical compound C1=CC=CC2=C(C(=O)COC(C)=O)C(OCC)=CC=C21 IBFXZGKNUYQYGX-UHFFFAOYSA-N 0.000 description 1
• JKUCADJWECJURN-UHFFFAOYSA-N [2-(3-methyl-1-benzothiophen-2-yl)-2-oxoethyl] acetate Chemical compound C1=CC=C2C(C)=C(C(=O)COC(=O)C)SC2=C1 JKUCADJWECJURN-UHFFFAOYSA-N 0.000 description 1
• DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
• 150000001241 acetals Chemical class 0.000 description 1
• HXGDTGSAIMULJN-UHFFFAOYSA-N acetnaphthylene Natural products C1=CC(C=C2)=C3C2=CC=CC3=C1 HXGDTGSAIMULJN-UHFFFAOYSA-N 0.000 description 1
• 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
• 150000007513 acids Chemical class 0.000 description 1
• 239000013543 active substance Substances 0.000 description 1
• 125000004442 acylamino group Chemical group 0.000 description 1
• 229960000643 adenine Drugs 0.000 description 1
• 201000007930 alcohol dependence Diseases 0.000 description 1
• 125000002723 alicyclic group Chemical group 0.000 description 1
• 125000001931 aliphatic group Chemical group 0.000 description 1
• 229910001413 alkali metal ion Inorganic materials 0.000 description 1
• 125000005119 alkyl cycloalkyl group Chemical group 0.000 description 1
• XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 description 1
• 125000000320 amidine group Chemical group 0.000 description 1
• 150000001413 amino acids Chemical class 0.000 description 1
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
• 150000001449 anionic compounds Chemical class 0.000 description 1
• 150000001450 anions Chemical class 0.000 description 1
• 125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
• 230000036506 anxiety Effects 0.000 description 1
• 239000011260 aqueous acid Substances 0.000 description 1
• 239000007864 aqueous solution Substances 0.000 description 1
• 239000003125 aqueous solvent Substances 0.000 description 1
• ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
• 150000001491 aromatic compounds Chemical class 0.000 description 1
• 208000006673 asthma Diseases 0.000 description 1
• 238000011914 asymmetric synthesis Methods 0.000 description 1
• 239000012298 atmosphere Substances 0.000 description 1
• HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 1
• 230000009286 beneficial effect Effects 0.000 description 1
• 230000008901 benefit Effects 0.000 description 1
• BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical compound C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 description 1
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
• QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
• 239000012964 benzotriazole Substances 0.000 description 1
• SHOMMGQAMRXRRK-UHFFFAOYSA-N bicyclo[3.1.1]heptane Chemical compound C1C2CC1CCC2 SHOMMGQAMRXRRK-UHFFFAOYSA-N 0.000 description 1
• 239000004305 biphenyl Substances 0.000 description 1
• 235000010290 biphenyl Nutrition 0.000 description 1
• BEWYHVAWEKZDPP-UHFFFAOYSA-N bornane Chemical compound C1CC2(C)CCC1C2(C)C BEWYHVAWEKZDPP-UHFFFAOYSA-N 0.000 description 1
• 229930006742 bornane Natural products 0.000 description 1
• 125000005620 boronic acid group Chemical group 0.000 description 1
• 229940098773 bovine serum albumin Drugs 0.000 description 1
• 125000001246 bromo group Chemical group Br* 0.000 description 1
• 125000003865 brosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)S(*)(=O)=O 0.000 description 1
• 239000011575 calcium Substances 0.000 description 1
• 229910052791 calcium Inorganic materials 0.000 description 1
• 229930006739 camphene Natural products 0.000 description 1
• ZYPYEBYNXWUCEA-UHFFFAOYSA-N camphenilone Natural products C1CC2C(=O)C(C)(C)C1C2 ZYPYEBYNXWUCEA-UHFFFAOYSA-N 0.000 description 1
• 239000002775 capsule Substances 0.000 description 1
• 229930006741 carane Natural products 0.000 description 1
• 239000004202 carbamide Substances 0.000 description 1
• 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 1
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
• 239000001768 carboxy methyl cellulose Substances 0.000 description 1
• 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
• 150000001733 carboxylic acid esters Chemical class 0.000 description 1
• 125000002843 carboxylic acid group Chemical group 0.000 description 1
• 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
• 150000001767 cationic compounds Chemical class 0.000 description 1
• 238000005119 centrifugation Methods 0.000 description 1
• 239000003153 chemical reaction reagent Substances 0.000 description 1
• 125000001309 chloro group Chemical group Cl* 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
• QZHPTGXQGDFGEN-UHFFFAOYSA-N chromene Chemical compound C1=CC=C2C=C[CH]OC2=C1 QZHPTGXQGDFGEN-UHFFFAOYSA-N 0.000 description 1
• 229940125773 compound 10 Drugs 0.000 description 1
• 230000008602 contraction Effects 0.000 description 1
• 230000008878 coupling Effects 0.000 description 1
• 238000010168 coupling process Methods 0.000 description 1
• 238000002425 crystallisation Methods 0.000 description 1
• ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 1
• 125000000392 cycloalkenyl group Chemical group 0.000 description 1
• CFBGXYDUODCMNS-UHFFFAOYSA-N cyclobutene Chemical compound C1CC=C1 CFBGXYDUODCMNS-UHFFFAOYSA-N 0.000 description 1
• 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 1
• ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 description 1
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
• 125000000298 cyclopropenyl group Chemical group [H]C1=C([H])C1([H])* 0.000 description 1
• 125000001295 dansyl group Chemical group [H]C1=C([H])C(N(C([H])([H])[H])C([H])([H])[H])=C2C([H])=C([H])C([H])=C(C2=C1[H])S(*)(=O)=O 0.000 description 1
• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 230000001419 dependent effect Effects 0.000 description 1
• AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 1
• 125000004663 dialkyl amino group Chemical group 0.000 description 1
• ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
• 239000012895 dilution Substances 0.000 description 1
• 238000010790 dilution Methods 0.000 description 1
• ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
• 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
• 201000010099 disease Diseases 0.000 description 1
• 235000019301 disodium ethylene diamine tetraacetate Nutrition 0.000 description 1
• 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 231100000673 dose–response relationship Toxicity 0.000 description 1
• 229940079593 drug Drugs 0.000 description 1
• 201000006549 dyspepsia Diseases 0.000 description 1
• 238000010828 elution Methods 0.000 description 1
• 239000000839 emulsion Substances 0.000 description 1
• 150000002081 enamines Chemical class 0.000 description 1
• 150000002085 enols Chemical class 0.000 description 1
• 125000004185 ester group Chemical group 0.000 description 1
• RQIFXTOWUNAUJC-UHFFFAOYSA-N ethanesulfinic acid Chemical compound CCS(O)=O RQIFXTOWUNAUJC-UHFFFAOYSA-N 0.000 description 1
• 125000001033 ether group Chemical group 0.000 description 1
• 125000004494 ethyl ester group Chemical group 0.000 description 1
• 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
• 230000007717 exclusion Effects 0.000 description 1
• 230000004761 fibrosis Effects 0.000 description 1
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
• 238000001640 fractional crystallisation Methods 0.000 description 1
• 230000030135 gastric motility Effects 0.000 description 1
• 208000021302 gastroesophageal reflux disease Diseases 0.000 description 1
• 239000000499 gel Substances 0.000 description 1
• 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 1
• 229940093915 gynecological organic acid Drugs 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 102000045993 human HTR2C Human genes 0.000 description 1
• BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
• 150000002430 hydrocarbons Chemical class 0.000 description 1
• 230000007062 hydrolysis Effects 0.000 description 1
• 238000006460 hydrolysis reaction Methods 0.000 description 1
• UWYVPFMHMJIBHE-OWOJBTEDSA-N hydroxymaleic acid group Chemical group O/C(/C(=O)O)=C/C(=O)O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
• 206010020718 hyperplasia Diseases 0.000 description 1
• 239000005457 ice water Substances 0.000 description 1
• 238000010348 incorporation Methods 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
• 239000004615 ingredient Substances 0.000 description 1
• 229910001412 inorganic anion Inorganic materials 0.000 description 1
• 150000007529 inorganic bases Chemical class 0.000 description 1
• 229910001411 inorganic cation Inorganic materials 0.000 description 1
• 229910052500 inorganic mineral Inorganic materials 0.000 description 1
• 238000007918 intramuscular administration Methods 0.000 description 1
• 238000007913 intrathecal administration Methods 0.000 description 1
• 238000001990 intravenous administration Methods 0.000 description 1
• 208000002551 irritable bowel syndrome Diseases 0.000 description 1
• 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
• HEBMCVBCEDMUOF-UHFFFAOYSA-N isochromane Chemical compound C1=CC=C2COCCC2=C1 HEBMCVBCEDMUOF-UHFFFAOYSA-N 0.000 description 1
• GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 1
• 229960004592 isopropanol Drugs 0.000 description 1
• 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
• 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 1
• 229960005417 ketanserin Drugs 0.000 description 1
• QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
• 239000003446 ligand Substances 0.000 description 1
• 239000006193 liquid solution Substances 0.000 description 1
• 239000006194 liquid suspension Substances 0.000 description 1
• 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 1
• 238000004519 manufacturing process Methods 0.000 description 1
• 229960003194 meglumine Drugs 0.000 description 1
• 239000000155 melt Substances 0.000 description 1
• 229950008693 mesulergine Drugs 0.000 description 1
• YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 1
• 125000006431 methyl cyclopropyl group Chemical group 0.000 description 1
• 150000004702 methyl esters Chemical class 0.000 description 1
• GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
• 206010027599 migraine Diseases 0.000 description 1
• 235000010755 mineral Nutrition 0.000 description 1
• 239000011707 mineral Substances 0.000 description 1
• 150000007522 mineralic acids Chemical class 0.000 description 1
• 230000004048 modification Effects 0.000 description 1
• 238000012986 modification Methods 0.000 description 1
• 125000002950 monocyclic group Chemical group 0.000 description 1
• 150000004682 monohydrates Chemical class 0.000 description 1
• 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
• 235000019796 monopotassium phosphate Nutrition 0.000 description 1
• 125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 description 1
• 230000004899 motility Effects 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
• MRHQBBSKCLIMRH-UHFFFAOYSA-N n-(acetamidomethoxymethyl)acetamide Chemical compound CC(=O)NCOCNC(C)=O MRHQBBSKCLIMRH-UHFFFAOYSA-N 0.000 description 1
• GTWJETSWSUWSEJ-UHFFFAOYSA-N n-benzylaniline Chemical compound C=1C=CC=CC=1CNC1=CC=CC=C1 GTWJETSWSUWSEJ-UHFFFAOYSA-N 0.000 description 1
• 125000006606 n-butoxy group Chemical group 0.000 description 1
• 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
• HUMMCEUVDBVXTQ-UHFFFAOYSA-N naphthalen-1-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC=CC2=C1 HUMMCEUVDBVXTQ-UHFFFAOYSA-N 0.000 description 1
• KVBGVZZKJNLNJU-UHFFFAOYSA-M naphthalene-2-sulfonate Chemical compound C1=CC=CC2=CC(S(=O)(=O)[O-])=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-M 0.000 description 1
• 125000001624 naphthyl group Chemical group 0.000 description 1
• 208000004296 neuralgia Diseases 0.000 description 1
• 239000002858 neurotransmitter agent Substances 0.000 description 1
• GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
• 125000001400 nonyl 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])[H] 0.000 description 1
• UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
• 238000010899 nucleation Methods 0.000 description 1
• LUHFJLLCZSYACL-UHFFFAOYSA-N o-(2,2,2-trichloroethyl)hydroxylamine Chemical compound NOCC(Cl)(Cl)Cl LUHFJLLCZSYACL-UHFFFAOYSA-N 0.000 description 1
• GWCBVFMHGHMALR-UHFFFAOYSA-N o-(2-trimethylsilylethyl)hydroxylamine Chemical compound C[Si](C)(C)CCON GWCBVFMHGHMALR-UHFFFAOYSA-N 0.000 description 1
• XYEOALKITRFCJJ-UHFFFAOYSA-N o-benzylhydroxylamine Chemical compound NOCC1=CC=CC=C1 XYEOALKITRFCJJ-UHFFFAOYSA-N 0.000 description 1
• KKVUFSINQFSJNK-UHFFFAOYSA-N o-tert-butylhydroxylamine Chemical compound CC(C)(C)ON KKVUFSINQFSJNK-UHFFFAOYSA-N 0.000 description 1
• 230000000414 obstructive effect Effects 0.000 description 1
• 125000002347 octyl 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])[H] 0.000 description 1
• ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
• 230000003287 optical effect Effects 0.000 description 1
• 210000000056 organ Anatomy 0.000 description 1
• 150000007524 organic acids Chemical class 0.000 description 1
• 235000005985 organic acids Nutrition 0.000 description 1
• 150000002892 organic cations Chemical class 0.000 description 1
• 239000003960 organic solvent Substances 0.000 description 1
• 125000002524 organometallic group Chemical group 0.000 description 1
• GUVKYQNSMXSMMU-UHFFFAOYSA-N oxane Chemical compound C1CCOCC1.C1CCOCC1 GUVKYQNSMXSMMU-UHFFFAOYSA-N 0.000 description 1
• NFBOHOGPQUYFRF-UHFFFAOYSA-N oxanthrene Chemical compound C1=CC=C2OC3=CC=CC=C3OC2=C1 NFBOHOGPQUYFRF-UHFFFAOYSA-N 0.000 description 1
• ATYBXHSAIOKLMG-UHFFFAOYSA-N oxepin Chemical compound O1C=CC=CC=C1 ATYBXHSAIOKLMG-UHFFFAOYSA-N 0.000 description 1
• AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
• 150000002923 oximes Chemical class 0.000 description 1
• 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
• CFJYNSNXFXLKNS-UHFFFAOYSA-N p-menthane Chemical compound CC(C)C1CCC(C)CC1 CFJYNSNXFXLKNS-UHFFFAOYSA-N 0.000 description 1
• IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
• 208000019906 panic disease Diseases 0.000 description 1
• RUVINXPYWBROJD-UHFFFAOYSA-N para-methoxyphenyl Natural products COC1=CC=C(C=CC)C=C1 RUVINXPYWBROJD-UHFFFAOYSA-N 0.000 description 1
• 238000007911 parenteral administration Methods 0.000 description 1
• 125000002958 pentadecyl 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])C([H])([H])[H] 0.000 description 1
• NQFOGDIWKQWFMN-UHFFFAOYSA-N phenalene Chemical compound C1=CC([CH]C=C2)=C3C2=CC=CC3=C1 NQFOGDIWKQWFMN-UHFFFAOYSA-N 0.000 description 1
• 229960003531 phenolsulfonphthalein Drugs 0.000 description 1
• 229950000688 phenothiazine Drugs 0.000 description 1
• GJSGGHOYGKMUPT-UHFFFAOYSA-N phenoxathiine Chemical compound C1=CC=C2OC3=CC=CC=C3SC2=C1 GJSGGHOYGKMUPT-UHFFFAOYSA-N 0.000 description 1
• WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
• 229930015698 phenylpropene Natural products 0.000 description 1
• LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
• 125000005545 phthalimidyl group Chemical group 0.000 description 1
• 239000006187 pill Substances 0.000 description 1
• 229930006728 pinane Natural products 0.000 description 1
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
• 229920001515 polyalkylene glycol Polymers 0.000 description 1
• 235000011056 potassium acetate Nutrition 0.000 description 1
• GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
• 238000002953 preparative HPLC Methods 0.000 description 1
• 201000011264 priapism Diseases 0.000 description 1
• 150000003138 primary alcohols Chemical class 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
• 229960003081 probenecid Drugs 0.000 description 1
• 125000006238 prop-1-en-1-yl group Chemical group [H]\C(*)=C(/[H])C([H])([H])[H] 0.000 description 1
• QROGIFZRVHSFLM-UHFFFAOYSA-N prop-1-enylbenzene Chemical compound CC=CC1=CC=CC=C1 QROGIFZRVHSFLM-UHFFFAOYSA-N 0.000 description 1
• YRNAXPCUXXETST-UHFFFAOYSA-N prop-1-enylcyclopentane Chemical compound CC=CC1CCCC1 YRNAXPCUXXETST-UHFFFAOYSA-N 0.000 description 1
• 230000000069 prophylactic effect Effects 0.000 description 1
• 238000011321 prophylaxis Methods 0.000 description 1
• 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
• 208000002815 pulmonary hypertension Diseases 0.000 description 1
• 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
• 125000001453 quaternary ammonium group Chemical group 0.000 description 1
• JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
• 230000005855 radiation Effects 0.000 description 1
• 150000003254 radicals Chemical class 0.000 description 1
• 239000000376 reactant Substances 0.000 description 1
• 239000011541 reaction mixture Substances 0.000 description 1
• 230000009467 reduction Effects 0.000 description 1
• 208000023504 respiratory system disease Diseases 0.000 description 1
• 230000002441 reversible effect Effects 0.000 description 1
• 125000005920 sec-butoxy group Chemical group 0.000 description 1
• 238000000926 separation method Methods 0.000 description 1
• 229940076279 serotonin Drugs 0.000 description 1
• 238000007493 shaping process Methods 0.000 description 1
• 239000000377 silicon dioxide Substances 0.000 description 1
• 208000019116 sleep disease Diseases 0.000 description 1
• 208000020685 sleep-wake disease Diseases 0.000 description 1
• 210000002460 smooth muscle Anatomy 0.000 description 1
• 239000012312 sodium hydride Substances 0.000 description 1
• 229910000104 sodium hydride Inorganic materials 0.000 description 1
• 239000008247 solid mixture Substances 0.000 description 1
• 229910001220 stainless steel Inorganic materials 0.000 description 1
• 239000010935 stainless steel Substances 0.000 description 1
• 239000012258 stirred mixture Substances 0.000 description 1
• 238000007920 subcutaneous administration Methods 0.000 description 1
• 125000003107 substituted aryl group Chemical group 0.000 description 1
• BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 1
• 125000001010 sulfinic acid amide group Chemical group 0.000 description 1
• 150000003451 sulfinic acid amides Chemical class 0.000 description 1
• 150000003453 sulfinic acid esters Chemical class 0.000 description 1
• 125000000213 sulfino group Chemical group [H]OS(*)=O 0.000 description 1
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
• 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
• 229940124530 sulfonamide Drugs 0.000 description 1
• 150000003456 sulfonamides Chemical class 0.000 description 1
• BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
• 125000001174 sulfone group Chemical group 0.000 description 1
• 150000003459 sulfonic acid esters Chemical class 0.000 description 1
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
• 150000003462 sulfoxides Chemical class 0.000 description 1
• 229910021653 sulphate ion Inorganic materials 0.000 description 1
• 239000010414 supernatant solution Substances 0.000 description 1
• 239000000829 suppository Substances 0.000 description 1
• 238000013268 sustained release Methods 0.000 description 1
• 239000012730 sustained-release form Substances 0.000 description 1
• 208000024891 symptom Diseases 0.000 description 1
• 238000001308 synthesis method Methods 0.000 description 1
• 239000003826 tablet Substances 0.000 description 1
• 230000036263 tachygastria Effects 0.000 description 1
• LRBQNJMCXXYXIU-NRMVVENXSA-N tannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-NRMVVENXSA-N 0.000 description 1
• 235000015523 tannic acid Nutrition 0.000 description 1
• 229940033123 tannic acid Drugs 0.000 description 1
• 229920002258 tannic acid Polymers 0.000 description 1
• 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• FGTJJHCZWOVVNH-UHFFFAOYSA-N tert-butyl-[tert-butyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)O[Si](C)(C)C(C)(C)C FGTJJHCZWOVVNH-UHFFFAOYSA-N 0.000 description 1
• 125000003831 tetrazolyl group Chemical group 0.000 description 1
• GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 description 1
• JWCVYQRPINPYQJ-UHFFFAOYSA-N thiepane Chemical compound C1CCCSCC1 JWCVYQRPINPYQJ-UHFFFAOYSA-N 0.000 description 1
• XSROQCDVUIHRSI-UHFFFAOYSA-N thietane Chemical compound C1CSC1 XSROQCDVUIHRSI-UHFFFAOYSA-N 0.000 description 1
• VOVUARRWDCVURC-UHFFFAOYSA-N thiirane Chemical compound C1CS1 VOVUARRWDCVURC-UHFFFAOYSA-N 0.000 description 1
• 125000005300 thiocarboxy group Chemical group C(=S)(O)* 0.000 description 1
• 150000003566 thiocarboxylic acids Chemical class 0.000 description 1
• BQAJJINKFRRSFO-UHFFFAOYSA-N thiolane Chemical compound C1CCSC1.C1CCSC1 BQAJJINKFRRSFO-UHFFFAOYSA-N 0.000 description 1
• 125000005505 thiomorpholino group Chemical group 0.000 description 1
• 239000011135 tin Substances 0.000 description 1
• 229910052718 tin Inorganic materials 0.000 description 1
• 230000000699 topical effect Effects 0.000 description 1
• 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
• 238000011269 treatment regimen Methods 0.000 description 1
• 150000003626 triacylglycerols Chemical class 0.000 description 1
• 125000002889 tridecyl 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])[H] 0.000 description 1
• ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
• ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
• 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
• 150000004684 trihydrates Chemical class 0.000 description 1
• 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 229960000281 trometamol Drugs 0.000 description 1
• 239000012588 trypsin Substances 0.000 description 1
• WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
• 229910052721 tungsten Inorganic materials 0.000 description 1
• 239000010937 tungsten Substances 0.000 description 1
• 210000004291 uterus Anatomy 0.000 description 1
• PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
• 229910052725 zinc Inorganic materials 0.000 description 1
• 239000011701 zinc Substances 0.000 description 1
• GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1