NO311800B1 - Arylpyrimidinderivater - Google Patents
Arylpyrimidinderivater Download PDFInfo
- Publication number
- NO311800B1 NO311800B1 NO19985392A NO985392A NO311800B1 NO 311800 B1 NO311800 B1 NO 311800B1 NO 19985392 A NO19985392 A NO 19985392A NO 985392 A NO985392 A NO 985392A NO 311800 B1 NO311800 B1 NO 311800B1
- Authority
- NO
- Norway
- Prior art keywords
- formula
- amino
- alkyl
- hydrogen
- fluoronaphth
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 273
- -1 C 1 -C 6 -thioalkoxy Chemical group 0.000 claims description 117
- 229910052739 hydrogen Inorganic materials 0.000 claims description 108
- 239000001257 hydrogen Substances 0.000 claims description 97
- 150000002431 hydrogen Chemical class 0.000 claims description 51
- 125000000217 alkyl group Chemical group 0.000 claims description 50
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 46
- 229940044551 receptor antagonist Drugs 0.000 claims description 46
- 239000002464 receptor antagonist Substances 0.000 claims description 46
- 102000006969 5-HT2B Serotonin Receptor Human genes 0.000 claims description 34
- 238000011282 treatment Methods 0.000 claims description 32
- 150000001204 N-oxides Chemical class 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 29
- 108010072584 5-HT2B Serotonin Receptor Proteins 0.000 claims description 24
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 201000010099 disease Diseases 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 239000008194 pharmaceutical composition Substances 0.000 claims description 13
- 208000019695 Migraine disease Diseases 0.000 claims description 11
- 206010027599 migraine Diseases 0.000 claims description 10
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 231100000252 nontoxic Toxicity 0.000 claims description 9
- 230000003000 nontoxic effect Effects 0.000 claims description 9
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 6
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 6
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 6
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 208000019906 panic disease Diseases 0.000 claims description 5
- 208000019116 sleep disease Diseases 0.000 claims description 5
- MZBVNYACSSGXID-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-1-benzazepine Chemical compound N1CCCCC2=CC=CC=C21 MZBVNYACSSGXID-UHFFFAOYSA-N 0.000 claims description 4
- OCTPNNXNZIKRQD-UHFFFAOYSA-N 4-(1h-indol-4-yl)-6-methylpyrimidin-2-amine Chemical compound NC1=NC(C)=CC(C=2C=3C=CNC=3C=CC=2)=N1 OCTPNNXNZIKRQD-UHFFFAOYSA-N 0.000 claims description 4
- ZJDHMXXAUNIDMN-UHFFFAOYSA-N 4-methyl-6-(2-methylnaphthalen-1-yl)pyrimidin-2-amine Chemical compound NC1=NC(C)=CC(C=2C3=CC=CC=C3C=CC=2C)=N1 ZJDHMXXAUNIDMN-UHFFFAOYSA-N 0.000 claims description 4
- 208000007848 Alcoholism Diseases 0.000 claims description 4
- 208000000103 Anorexia Nervosa Diseases 0.000 claims description 4
- 208000011688 Generalised anxiety disease Diseases 0.000 claims description 4
- 201000007930 alcohol dependence Diseases 0.000 claims description 4
- 239000000969 carrier Substances 0.000 claims description 4
- 208000029364 generalized anxiety disease Diseases 0.000 claims description 4
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 4
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 4
- 201000011264 priapism Diseases 0.000 claims description 4
- DQFQCHIDRBIESA-UHFFFAOYSA-N 1-benzazepine Chemical compound N1C=CC=CC2=CC=CC=C12 DQFQCHIDRBIESA-UHFFFAOYSA-N 0.000 claims description 3
- OMRSFKWMIDIMKJ-UHFFFAOYSA-N 1h,3h-naphtho[1,8-cd]pyran Chemical compound C1=CC(COC2)=C3C2=CC=CC3=C1 OMRSFKWMIDIMKJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000004562 2,3-dihydroindol-1-yl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 3
- IDORDOZYEQUFCB-UHFFFAOYSA-N 2-[2-amino-6-(4-fluoronaphthalen-1-yl)pyrimidin-4-yl]propan-2-ol Chemical compound NC1=NC(C(C)(O)C)=CC(C=2C3=CC=CC=C3C(F)=CC=2)=N1 IDORDOZYEQUFCB-UHFFFAOYSA-N 0.000 claims description 3
- PVTXJGJDOHYFOX-UHFFFAOYSA-N 2h-1,4-benzoxazine Chemical compound C1=CC=C2N=CCOC2=C1 PVTXJGJDOHYFOX-UHFFFAOYSA-N 0.000 claims description 3
- YRLORWPBJZEGBX-UHFFFAOYSA-N 3,4-dihydro-2h-1,4-benzoxazine Chemical compound C1=CC=C2NCCOC2=C1 YRLORWPBJZEGBX-UHFFFAOYSA-N 0.000 claims description 3
- GWTKMBYGQYMGQT-UHFFFAOYSA-N 4-(4-fluoronaphthalen-1-yl)-6-(2-methylpropyl)pyrimidin-2-amine Chemical compound NC1=NC(CC(C)C)=CC(C=2C3=CC=CC=C3C(F)=CC=2)=N1 GWTKMBYGQYMGQT-UHFFFAOYSA-N 0.000 claims description 3
- 206010020772 Hypertension Diseases 0.000 claims description 3
- 125000000593 indol-1-yl group Chemical group [H]C1=C([H])C([H])=C2N([*])C([H])=C([H])C2=C1[H] 0.000 claims description 3
- 229930192474 thiophene Natural products 0.000 claims description 3
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
- IVXIXZLZGOIECY-UHFFFAOYSA-N 4-(4,6-difluoronaphthalen-1-yl)-6-(2-fluoropropan-2-yl)pyrimidin-2-amine Chemical compound NC1=NC(C(C)(F)C)=CC(C=2C3=CC=C(F)C=C3C(F)=CC=2)=N1 IVXIXZLZGOIECY-UHFFFAOYSA-N 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- 150000002475 indoles Chemical class 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 7
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 claims 1
- YPKBCLZFIYBSHK-UHFFFAOYSA-N 5-methylindole Chemical compound CC1=CC=C2NC=CC2=C1 YPKBCLZFIYBSHK-UHFFFAOYSA-N 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 238000002360 preparation method Methods 0.000 description 87
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 73
- 238000000034 method Methods 0.000 description 70
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
- 238000006243 chemical reaction Methods 0.000 description 65
- 239000000203 mixture Substances 0.000 description 59
- 239000000243 solution Substances 0.000 description 47
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 38
- 102000006902 5-HT2C Serotonin Receptor Human genes 0.000 description 32
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 30
- 235000019441 ethanol Nutrition 0.000 description 29
- 239000007787 solid Substances 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- 229960004756 ethanol Drugs 0.000 description 27
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- 239000000047 product Substances 0.000 description 27
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 26
- 108010072553 5-HT2C Serotonin Receptor Proteins 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000002904 solvent Substances 0.000 description 24
- 230000000694 effects Effects 0.000 description 22
- 230000001225 therapeutic effect Effects 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 17
- 239000011541 reaction mixture Substances 0.000 description 16
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
- 238000010992 reflux Methods 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- 208000019901 Anxiety disease Diseases 0.000 description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
- 230000036506 anxiety Effects 0.000 description 12
- 238000004587 chromatography analysis Methods 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 102000049773 5-HT2A Serotonin Receptor Human genes 0.000 description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 11
- 239000000460 chlorine Substances 0.000 description 11
- 229910052801 chlorine Inorganic materials 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 241000700159 Rattus Species 0.000 description 10
- 230000027455 binding Effects 0.000 description 10
- STIAPHVBRDNOAJ-UHFFFAOYSA-N carbamimidoylazanium;carbonate Chemical compound NC(N)=N.NC(N)=N.OC(O)=O STIAPHVBRDNOAJ-UHFFFAOYSA-N 0.000 description 10
- 210000004027 cell Anatomy 0.000 description 10
- 101150075901 htr2 gene Proteins 0.000 description 10
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 10
- ZZZQXCUPAJFVBN-UHFFFAOYSA-N 4-(4-fluoronaphthalen-1-yl)-6-propan-2-ylpyrimidin-2-amine Chemical compound NC1=NC(C(C)C)=CC(C=2C3=CC=CC=C3C(F)=CC=2)=N1 ZZZQXCUPAJFVBN-UHFFFAOYSA-N 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 241000699670 Mus sp. Species 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- BHKKSKOHRFHHIN-MRVPVSSYSA-N 1-[[2-[(1R)-1-aminoethyl]-4-chlorophenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound N[C@H](C)C1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)Cl BHKKSKOHRFHHIN-MRVPVSSYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 241000699666 Mus <mouse, genus> Species 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 239000012312 sodium hydride Substances 0.000 description 8
- 229910000104 sodium hydride Inorganic materials 0.000 description 8
- VHFVKMTVMIZMIK-UHFFFAOYSA-N 1-(3-chlorophenyl)piperazine Chemical compound ClC1=CC=CC(N2CCNCC2)=C1 VHFVKMTVMIZMIK-UHFFFAOYSA-N 0.000 description 7
- 101710138093 5-hydroxytryptamine receptor 2C Proteins 0.000 description 7
- 102100024959 5-hydroxytryptamine receptor 2C Human genes 0.000 description 7
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 239000002552 dosage form Substances 0.000 description 7
- 229940079593 drug Drugs 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- 229910052763 palladium Inorganic materials 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 239000000018 receptor agonist Substances 0.000 description 7
- 229940044601 receptor agonist Drugs 0.000 description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 229940116892 5 Hydroxytryptamine 2B receptor antagonist Drugs 0.000 description 6
- 108010072564 5-HT2A Serotonin Receptor Proteins 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
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 6
- 101150013372 Htr2c gene Proteins 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- 230000000949 anxiolytic effect Effects 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 6
- 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 6
- 239000000546 pharmaceutical excipient Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000002287 radioligand Substances 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000012442 inert solvent Substances 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 239000003446 ligand Substances 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 239000003586 protic polar solvent Substances 0.000 description 5
- 239000012723 sample buffer Substances 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 208000024891 symptom Diseases 0.000 description 5
- 150000005724 2-amino-4-chloropyrimidines Chemical class 0.000 description 4
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 4
- UBBADIOUYJCYLV-UHFFFAOYSA-N 4-(4-fluoronaphthalen-1-yl)-2-methylsulfanyl-6-(2-phenylethyl)pyrimidine Chemical compound C=1C(C=2C3=CC=CC=C3C(F)=CC=2)=NC(SC)=NC=1CCC1=CC=CC=C1 UBBADIOUYJCYLV-UHFFFAOYSA-N 0.000 description 4
- VTGWQEWPQSFQCM-UHFFFAOYSA-N 4-(4-fluoronaphthalen-1-yl)-2-methylsulfonyl-6-propan-2-ylpyrimidine Chemical compound CS(=O)(=O)C1=NC(C(C)C)=CC(C=2C3=CC=CC=C3C(F)=CC=2)=N1 VTGWQEWPQSFQCM-UHFFFAOYSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- ICLCYJSVXCHCAR-UHFFFAOYSA-N 4-chloro-2-methylsulfanyl-6-propan-2-ylpyrimidine Chemical compound CSC1=NC(Cl)=CC(C(C)C)=N1 ICLCYJSVXCHCAR-UHFFFAOYSA-N 0.000 description 4
- RRMVDLLCVGZDMH-UHFFFAOYSA-N 4-chloro-5,6-dimethylpyrimidin-2-amine Chemical compound CC1=NC(N)=NC(Cl)=C1C RRMVDLLCVGZDMH-UHFFFAOYSA-N 0.000 description 4
- 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 description 4
- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 description 4
- OCOHPSHRDKBGOZ-UHFFFAOYSA-N 6-methyl-2-methylsulfanyl-1h-pyrimidin-4-one Chemical compound CSC1=NC(=O)C=C(C)N1 OCOHPSHRDKBGOZ-UHFFFAOYSA-N 0.000 description 4
- 206010012335 Dependence Diseases 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- 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 4
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 4
- 101150104779 HTR2A gene Proteins 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000005557 antagonist Substances 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 239000000872 buffer Substances 0.000 description 4
- 239000001913 cellulose Chemical class 0.000 description 4
- 229920002678 cellulose Chemical class 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000001684 chronic effect Effects 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- WDAXFOBOLVPGLV-UHFFFAOYSA-N ethyl isobutyrate Chemical compound CCOC(=O)C(C)C WDAXFOBOLVPGLV-UHFFFAOYSA-N 0.000 description 4
- 238000000338 in vitro Methods 0.000 description 4
- 238000007912 intraperitoneal administration Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- XTXCFTMJPRXBBC-UHFFFAOYSA-N methyl 4,4-dimethyl-3-oxopentanoate Chemical compound COC(=O)CC(=O)C(C)(C)C XTXCFTMJPRXBBC-UHFFFAOYSA-N 0.000 description 4
- HXRAMSFGUAOAJR-UHFFFAOYSA-N n,n,n',n'-tetramethyl-1-[(2-methylpropan-2-yl)oxy]methanediamine Chemical compound CN(C)C(N(C)C)OC(C)(C)C HXRAMSFGUAOAJR-UHFFFAOYSA-N 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 239000002798 polar solvent Substances 0.000 description 4
- 150000003230 pyrimidines Chemical class 0.000 description 4
- 102000005962 receptors Human genes 0.000 description 4
- 108020003175 receptors Proteins 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- JUQLTPCYUFPYKE-UHFFFAOYSA-N ritanserin Chemical compound CC=1N=C2SC=CN2C(=O)C=1CCN(CC1)CCC1=C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 JUQLTPCYUFPYKE-UHFFFAOYSA-N 0.000 description 4
- 229950009626 ritanserin Drugs 0.000 description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
- 150000003335 secondary amines Chemical class 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000829 suppository Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 4
- SWSQBOPZIKWTGO-UHFFFAOYSA-N 1,1-dimethylguanidine Chemical compound CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- XFNSNAKAEWWMCR-UHFFFAOYSA-N 1-(1h-indol-4-yl)butane-1,3-dione Chemical compound CC(=O)CC(=O)C1=CC=CC2=C1C=CN2 XFNSNAKAEWWMCR-UHFFFAOYSA-N 0.000 description 3
- RUBNGGWBJUGNNA-UHFFFAOYSA-N 1-(1h-indol-4-yl)ethanone Chemical compound CC(=O)C1=CC=CC2=C1C=CN2 RUBNGGWBJUGNNA-UHFFFAOYSA-N 0.000 description 3
- CJIVJXVUVYWRAY-UHFFFAOYSA-N 1-(4,7-difluoronaphthalen-1-yl)ethanone Chemical compound C1=C(F)C=C2C(C(=O)C)=CC=C(F)C2=C1 CJIVJXVUVYWRAY-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- NPTGVVKPLWFPPX-UHFFFAOYSA-N 2-amino-4-chloro-6-methylpyrimidine Chemical compound CC1=CC(Cl)=NC(N)=N1 NPTGVVKPLWFPPX-UHFFFAOYSA-N 0.000 description 3
- DUBAZDUHEAIVOH-UHFFFAOYSA-N 4-(4-fluoronaphthalen-2-yl)-6-methyl-2-methylsulfanylpyrimidine Chemical compound CSC1=NC(C)=CC(C=2C=C3C=CC=CC3=C(F)C=2)=N1 DUBAZDUHEAIVOH-UHFFFAOYSA-N 0.000 description 3
- BUSNQRJIWVQULW-UHFFFAOYSA-N 4-chloro-6-(3,4-dihydro-2h-quinolin-1-yl)pyrimidin-2-amine Chemical compound NC1=NC(Cl)=CC(N2C3=CC=CC=C3CCC2)=N1 BUSNQRJIWVQULW-UHFFFAOYSA-N 0.000 description 3
- LAMDKQQOSGMNSB-UHFFFAOYSA-N 4-chloro-6-propylpyrimidin-2-amine Chemical compound CCCC1=CC(Cl)=NC(N)=N1 LAMDKQQOSGMNSB-UHFFFAOYSA-N 0.000 description 3
- JXXAWQORKBZWRB-UHFFFAOYSA-N 4-methyl-6-naphthalen-1-ylpyrimidin-2-amine Chemical compound NC1=NC(C)=CC(C=2C3=CC=CC=C3C=CC=2)=N1 JXXAWQORKBZWRB-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
- FRXSZNDVFUDTIR-UHFFFAOYSA-N 6-methoxy-1,2,3,4-tetrahydroquinoline Chemical compound N1CCCC2=CC(OC)=CC=C21 FRXSZNDVFUDTIR-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 208000030814 Eating disease Diseases 0.000 description 3
- 208000019454 Feeding and Eating disease Diseases 0.000 description 3
- 241000124008 Mammalia Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 3
- 239000002249 anxiolytic agent Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 235000010323 ascorbic acid Nutrition 0.000 description 3
- 229960005070 ascorbic acid Drugs 0.000 description 3
- 239000011668 ascorbic acid Substances 0.000 description 3
- 230000006399 behavior Effects 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 229960003920 cocaine Drugs 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 235000014632 disordered eating Nutrition 0.000 description 3
- 238000009509 drug development Methods 0.000 description 3
- DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 3
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 150000002357 guanidines Chemical class 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 150000007529 inorganic bases Chemical class 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 238000011835 investigation Methods 0.000 description 3
- 238000002955 isolation Methods 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
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 210000003205 muscle Anatomy 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 230000009871 nonspecific binding Effects 0.000 description 3
- 239000004533 oil dispersion Substances 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 230000037322 slow-wave sleep Effects 0.000 description 3
- 230000003997 social interaction Effects 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 229940035044 sorbitan monolaurate Drugs 0.000 description 3
- 238000013268 sustained release Methods 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 3
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 2
- FPIZOKREUZJMNO-UHFFFAOYSA-N 1,6-difluoronaphthalene Chemical compound FC1=CC=CC2=CC(F)=CC=C21 FPIZOKREUZJMNO-UHFFFAOYSA-N 0.000 description 2
- QOPCGRXGCDPQKK-UHFFFAOYSA-N 1-(2,3-dihydro-1,4-benzodioxin-5-yl)butane-1,3-dione Chemical compound O1CCOC2=C1C=CC=C2C(=O)CC(=O)C QOPCGRXGCDPQKK-UHFFFAOYSA-N 0.000 description 2
- WDHPUSKQPSPGFU-UHFFFAOYSA-N 1-(4,7-difluoronaphthalen-1-yl)-4-methylpentane-1,3-dione Chemical compound C1=C(F)C=C2C(C(=O)CC(=O)C(C)C)=CC=C(F)C2=C1 WDHPUSKQPSPGFU-UHFFFAOYSA-N 0.000 description 2
- VAUJZKBFENPOCH-UHFFFAOYSA-N 1-bromo-4-fluoronaphthalene Chemical compound C1=CC=C2C(F)=CC=C(Br)C2=C1 VAUJZKBFENPOCH-UHFFFAOYSA-N 0.000 description 2
- QQLIGMASAVJVON-UHFFFAOYSA-N 1-naphthalen-1-ylethanone Chemical compound C1=CC=C2C(C(=O)C)=CC=CC2=C1 QQLIGMASAVJVON-UHFFFAOYSA-N 0.000 description 2
- XQCZBXHVTFVIFE-UHFFFAOYSA-N 2-amino-4-hydroxypyrimidine Chemical class NC1=NC=CC(O)=N1 XQCZBXHVTFVIFE-UHFFFAOYSA-N 0.000 description 2
- LTKWJTJJGNNDAY-UHFFFAOYSA-N 2-amino-6-tert-butyl-1h-pyrimidin-4-one Chemical compound CC(C)(C)C1=CC(O)=NC(N)=N1 LTKWJTJJGNNDAY-UHFFFAOYSA-N 0.000 description 2
- FOEMIZSFFWGXHX-UHFFFAOYSA-N 2-methylsulfanylpyrimidine Chemical class CSC1=NC=CC=N1 FOEMIZSFFWGXHX-UHFFFAOYSA-N 0.000 description 2
- OIGXNHYFKZCTCH-UHFFFAOYSA-N 2-methylsulfonylpyrimidine Chemical class CS(=O)(=O)C1=NC=CC=N1 OIGXNHYFKZCTCH-UHFFFAOYSA-N 0.000 description 2
- UYHSQVMHSFXUOA-UHFFFAOYSA-N 2-methylthiouracil Chemical class CSC1=NC=CC(O)=N1 UYHSQVMHSFXUOA-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- XJPZKYIHCLDXST-UHFFFAOYSA-N 4,6-dichloropyrimidine Chemical class ClC1=CC(Cl)=NC=N1 XJPZKYIHCLDXST-UHFFFAOYSA-N 0.000 description 2
- BVDLDIWVBSTBRG-UHFFFAOYSA-N 4-(4-fluoronaphthalen-1-yl)-6-(2-fluoropropan-2-yl)pyrimidin-2-amine Chemical compound NC1=NC(C(C)(F)C)=CC(C=2C3=CC=CC=C3C(F)=CC=2)=N1 BVDLDIWVBSTBRG-UHFFFAOYSA-N 0.000 description 2
- RNQXYFJSJMPSRT-UHFFFAOYSA-N 4-(4-fluoronaphthalen-1-yl)-n-methyl-6-propan-2-ylpyrimidin-2-amine Chemical compound CNC1=NC(C(C)C)=CC(C=2C3=CC=CC=C3C(F)=CC=2)=N1 RNQXYFJSJMPSRT-UHFFFAOYSA-N 0.000 description 2
- WZGFRNRXEBUINW-UHFFFAOYSA-N 4-chloro-6-(3,4-dihydro-2h-quinolin-1-yl)pyrimidin-2-amine;hydrochloride Chemical compound Cl.NC1=NC(Cl)=CC(N2C3=CC=CC=C3CCC2)=N1 WZGFRNRXEBUINW-UHFFFAOYSA-N 0.000 description 2
- UGPHQHDVJUFTEX-UHFFFAOYSA-N 4-naphthalen-1-yl-6-propan-2-ylpyrimidin-2-amine Chemical compound NC1=NC(C(C)C)=CC(C=2C3=CC=CC=C3C=CC=2)=N1 UGPHQHDVJUFTEX-UHFFFAOYSA-N 0.000 description 2
- OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 description 2
- 101710138092 5-hydroxytryptamine receptor 2B Proteins 0.000 description 2
- 102100024956 5-hydroxytryptamine receptor 2B Human genes 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
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 2
- 229920002785 Croscarmellose sodium Polymers 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
- 208000020401 Depressive disease Diseases 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-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
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- DPWPWRLQFGFJFI-UHFFFAOYSA-N Pargyline Chemical compound C#CCN(C)CC1=CC=CC=C1 DPWPWRLQFGFJFI-UHFFFAOYSA-N 0.000 description 2
- 229920005372 Plexiglas® Polymers 0.000 description 2
- 229920002873 Polyethylenimine Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 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
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 239000000935 antidepressant agent Substances 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical class OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 210000004556 brain Anatomy 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 2
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
- 235000013985 cinnamic acid Nutrition 0.000 description 2
- 229930016911 cinnamic acid Natural products 0.000 description 2
- 235000015165 citric acid Nutrition 0.000 description 2
- 230000009137 competitive binding Effects 0.000 description 2
- 238000013270 controlled release Methods 0.000 description 2
- 229960001681 croscarmellose sodium Drugs 0.000 description 2
- 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 239000008121 dextrose Substances 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 2
- XCLDSQRVMMXWMS-UHFFFAOYSA-N ethyl 4-methyl-3-oxopentanoate Chemical compound CCOC(=O)CC(=O)C(C)C XCLDSQRVMMXWMS-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 208000030533 eye disease Diseases 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 235000011087 fumaric acid Nutrition 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 229940093915 gynecological organic acid Drugs 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000011539 homogenization buffer Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical compound C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000007972 injectable composition Substances 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 229960005417 ketanserin Drugs 0.000 description 2
- 239000008101 lactose Chemical class 0.000 description 2
- 230000006742 locomotor activity Effects 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 239000001630 malic acid Substances 0.000 description 2
- 235000011090 malic acid Nutrition 0.000 description 2
- 229960002510 mandelic acid Drugs 0.000 description 2
- 239000000594 mannitol Substances 0.000 description 2
- 235000010355 mannitol Nutrition 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- HUMMCEUVDBVXTQ-UHFFFAOYSA-N naphthalen-1-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC=CC2=C1 HUMMCEUVDBVXTQ-UHFFFAOYSA-N 0.000 description 2
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 2
- 229960002715 nicotine Drugs 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 239000006179 pH buffering agent Substances 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 229960001779 pargyline Drugs 0.000 description 2
- 238000005192 partition Methods 0.000 description 2
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 2
- 229940107700 pyruvic acid Drugs 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 2
- 229960004889 salicylic acid Drugs 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- 229940076279 serotonin Drugs 0.000 description 2
- 239000002891 serotonin 2B antagonist Substances 0.000 description 2
- 230000007958 sleep Effects 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 229960004249 sodium acetate Drugs 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 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
- 239000003381 stabilizer Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000012730 sustained-release form Substances 0.000 description 2
- 238000007910 systemic administration Methods 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 125000005309 thioalkoxy group Chemical group 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 1
- KRAIDHROQNRKJM-UHFFFAOYSA-N (4-fluoronaphthalen-1-yl)-dimethoxyborane Chemical compound C1=CC=C2C(B(OC)OC)=CC=C(F)C2=C1 KRAIDHROQNRKJM-UHFFFAOYSA-N 0.000 description 1
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 description 1
- ZTXVORLTNAYYPB-BTJKTKAUSA-N (z)-but-2-enedioic acid;2-[[4-(4-fluoronaphthalen-1-yl)-6-propan-2-ylpyrimidin-2-yl]amino]propane-1,3-diol Chemical compound OC(=O)\C=C/C(O)=O.OCC(CO)NC1=NC(C(C)C)=CC(C=2C3=CC=CC=C3C(F)=CC=2)=N1 ZTXVORLTNAYYPB-BTJKTKAUSA-N 0.000 description 1
- WENJLEWERIXVAX-BTJKTKAUSA-N (z)-but-2-enedioic acid;4-(4-fluoronaphthalen-1-yl)-6-(2-methoxyethyl)pyrimidin-2-amine Chemical compound OC(=O)\C=C/C(O)=O.NC1=NC(CCOC)=CC(C=2C3=CC=CC=C3C(F)=CC=2)=N1 WENJLEWERIXVAX-BTJKTKAUSA-N 0.000 description 1
- GEYNHUFSEYDEBB-BTJKTKAUSA-N (z)-but-2-enedioic acid;4-(4-fluoronaphthalen-1-yl)-6-(2-phenylethyl)pyrimidin-2-amine Chemical compound OC(=O)\C=C/C(O)=O.C=1C(C=2C3=CC=CC=C3C(F)=CC=2)=NC(N)=NC=1CCC1=CC=CC=C1 GEYNHUFSEYDEBB-BTJKTKAUSA-N 0.000 description 1
- AECBQAYOWYGGEP-BTJKTKAUSA-N (z)-but-2-enedioic acid;4-(4-fluoronaphthalen-1-yl)-6-propan-2-ylpyrimidin-2-amine Chemical compound OC(=O)\C=C/C(O)=O.NC1=NC(C(C)C)=CC(C=2C3=CC=CC=C3C(F)=CC=2)=N1 AECBQAYOWYGGEP-BTJKTKAUSA-N 0.000 description 1
- 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 1
- JCIIKRHCWVHVFF-UHFFFAOYSA-N 1,2,4-thiadiazol-5-amine;hydrochloride Chemical compound Cl.NC1=NC=NS1 JCIIKRHCWVHVFF-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- JHXQRHMYWAWDMZ-UHFFFAOYSA-N 1,2-difluoro-3-methylpentane Chemical compound CCC(C)C(F)CF JHXQRHMYWAWDMZ-UHFFFAOYSA-N 0.000 description 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- HYLFRICFKVJJOZ-UHFFFAOYSA-N 1-(1-methylindol-3-yl)ethanone Chemical compound C1=CC=C2C(C(=O)C)=CN(C)C2=C1 HYLFRICFKVJJOZ-UHFFFAOYSA-N 0.000 description 1
- QMXNXMGUQSFTHC-UHFFFAOYSA-N 1-(2,3-dihydro-1,4-benzodioxin-5-yl)ethanone Chemical compound O1CCOC2=C1C=CC=C2C(=O)C QMXNXMGUQSFTHC-UHFFFAOYSA-N 0.000 description 1
- MRBFGEHILMYPTF-UHFFFAOYSA-N 1-(2-Pyrimidyl)piperazine Chemical compound C1CNCCN1C1=NC=CC=N1 MRBFGEHILMYPTF-UHFFFAOYSA-N 0.000 description 1
- NAVKHJDRCGTULV-UHFFFAOYSA-N 1-(3-chlorophenyl)butane-1,3-dione Chemical compound CC(=O)CC(=O)C1=CC=CC(Cl)=C1 NAVKHJDRCGTULV-UHFFFAOYSA-N 0.000 description 1
- IGCOGOIEKULMHC-UHFFFAOYSA-N 1-(4,6-difluoronaphthalen-1-yl)ethanone Chemical compound FC1=CC=C2C(C(=O)C)=CC=C(F)C2=C1 IGCOGOIEKULMHC-UHFFFAOYSA-N 0.000 description 1
- ACLRBQOREGMBFQ-UHFFFAOYSA-N 1-(4,8-difluoronaphthalen-1-yl)ethanone Chemical compound C1=CC(F)=C2C(C(=O)C)=CC=C(F)C2=C1 ACLRBQOREGMBFQ-UHFFFAOYSA-N 0.000 description 1
- RSBOFKOICCVYNF-UHFFFAOYSA-N 1-(4-methoxynaphthalen-1-yl)ethanone Chemical compound C1=CC=C2C(OC)=CC=C(C(C)=O)C2=C1 RSBOFKOICCVYNF-UHFFFAOYSA-N 0.000 description 1
- COHCFLRPLGESQH-UHFFFAOYSA-N 1-[6-(4-fluoronaphthalen-1-yl)-2-[2-(methylamino)ethylamino]pyrimidin-4-yl]propan-2-ol;hydrochloride Chemical compound Cl.CNCCNC1=NC(CC(C)O)=CC(C=2C3=CC=CC=C3C(F)=CC=2)=N1 COHCFLRPLGESQH-UHFFFAOYSA-N 0.000 description 1
- DHIVLKMGKIZOHF-UHFFFAOYSA-N 1-fluorooctane Chemical compound CCCCCCCCF DHIVLKMGKIZOHF-UHFFFAOYSA-N 0.000 description 1
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 1
- LOWVNVYYWFTFII-UHFFFAOYSA-N 1-naphthalen-1-ylprop-2-en-1-one Chemical compound C1=CC=C2C(C(=O)C=C)=CC=CC2=C1 LOWVNVYYWFTFII-UHFFFAOYSA-N 0.000 description 1
- SWELIMKTDYHAOY-UHFFFAOYSA-N 2,4-diamino-6-hydroxypyrimidine Chemical compound NC1=CC(=O)N=C(N)N1 SWELIMKTDYHAOY-UHFFFAOYSA-N 0.000 description 1
- NVIOBEPTKDSPEQ-UHFFFAOYSA-N 2-(2-amino-6-naphthalen-1-ylpyrimidin-4-yl)oxyethanol;hydrochloride Chemical compound Cl.NC1=NC(OCCO)=CC(C=2C3=CC=CC=C3C=CC=2)=N1 NVIOBEPTKDSPEQ-UHFFFAOYSA-N 0.000 description 1
- YMOYQAIXEUUWFI-UHFFFAOYSA-N 2-(3,4-dihydro-2h-quinolin-1-yl)-n-methylpyrimidin-4-amine Chemical compound CNC1=CC=NC(N2C3=CC=CC=C3CCC2)=N1 YMOYQAIXEUUWFI-UHFFFAOYSA-N 0.000 description 1
- HPIQTHDLKVWCFJ-UHFFFAOYSA-N 2-[2-[6-(4-fluoronaphthalen-1-yl)-2-methylsulfanylpyrimidin-4-yl]ethyl]phenol Chemical compound C=1C(C=2C3=CC=CC=C3C(F)=CC=2)=NC(SC)=NC=1CCC1=CC=CC=C1O HPIQTHDLKVWCFJ-UHFFFAOYSA-N 0.000 description 1
- WGNFZTBHIGKRPN-UHFFFAOYSA-N 2-[2-[6-(4-fluoronaphthalen-1-yl)-2-methylsulfonylpyrimidin-4-yl]ethyl]phenol Chemical compound C=1C(C=2C3=CC=CC=C3C(F)=CC=2)=NC(S(=O)(=O)C)=NC=1CCC1=CC=CC=C1O WGNFZTBHIGKRPN-UHFFFAOYSA-N 0.000 description 1
- GBUNTDFJKYKDSW-UHFFFAOYSA-N 2-[2-[[4-(4-fluoronaphthalen-1-yl)-6-propan-2-ylpyrimidin-2-yl]amino]ethoxy]ethanol;hydrobromide Chemical compound Br.OCCOCCNC1=NC(C(C)C)=CC(C=2C3=CC=CC=C3C(F)=CC=2)=N1 GBUNTDFJKYKDSW-UHFFFAOYSA-N 0.000 description 1
- WIRYDPJMMDXELS-UHFFFAOYSA-N 2-[[4-(4-fluoronaphthalen-1-yl)-6-methoxypyrimidin-2-yl]amino]ethanol;hydrochloride Chemical compound Cl.OCCNC1=NC(OC)=CC(C=2C3=CC=CC=C3C(F)=CC=2)=N1 WIRYDPJMMDXELS-UHFFFAOYSA-N 0.000 description 1
- HXGMZRLECGCOBJ-UHFFFAOYSA-N 2-[[4-(4-fluoronaphthalen-1-yl)-6-propan-2-ylpyrimidin-2-yl]amino]ethanol;hydrochloride Chemical compound Cl.OCCNC1=NC(C(C)C)=CC(C=2C3=CC=CC=C3C(F)=CC=2)=N1 HXGMZRLECGCOBJ-UHFFFAOYSA-N 0.000 description 1
- 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 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
- APWRLAZEMYLHKZ-UHFFFAOYSA-N 2-amino-5,6-dimethyl-1h-pyrimidin-4-one Chemical compound CC=1NC(N)=NC(=O)C=1C APWRLAZEMYLHKZ-UHFFFAOYSA-N 0.000 description 1
- CBRFQLVEZWUNEN-UHFFFAOYSA-N 2-amino-5-fluoro-6-methyl-1h-pyrimidin-4-one Chemical compound CC=1NC(N)=NC(=O)C=1F CBRFQLVEZWUNEN-UHFFFAOYSA-N 0.000 description 1
- ICVOELCHCKJETJ-UHFFFAOYSA-N 2-amino-6-benzyl-1h-pyrimidin-4-one Chemical compound N1C(N)=NC(=O)C=C1CC1=CC=CC=C1 ICVOELCHCKJETJ-UHFFFAOYSA-N 0.000 description 1
- UGRIRCGEGYBIDF-UHFFFAOYSA-N 2-amino-6-butan-2-yl-1h-pyrimidin-4-one Chemical compound CCC(C)C1=CC(O)=NC(N)=N1 UGRIRCGEGYBIDF-UHFFFAOYSA-N 0.000 description 1
- DPODJNAGSYHJMQ-UHFFFAOYSA-N 2-amino-6-cyclobutyl-1h-pyrimidin-4-one Chemical compound NC1=NC(O)=CC(C2CCC2)=N1 DPODJNAGSYHJMQ-UHFFFAOYSA-N 0.000 description 1
- NFSXJRRDVVFGMU-UHFFFAOYSA-N 2-amino-6-cyclopentyl-1h-pyrimidin-4-one Chemical compound N1C(N)=NC(=O)C=C1C1CCCC1 NFSXJRRDVVFGMU-UHFFFAOYSA-N 0.000 description 1
- KGEQZBGKOFFIAI-UHFFFAOYSA-N 2-amino-6-cyclopropyl-1h-pyrimidin-4-one Chemical compound NC1=NC(O)=CC(C2CC2)=N1 KGEQZBGKOFFIAI-UHFFFAOYSA-N 0.000 description 1
- QDSSWFSXBZSFQO-UHFFFAOYSA-N 2-amino-6-ethyl-1h-pyrimidin-4-one Chemical compound CCC1=CC(=O)N=C(N)N1 QDSSWFSXBZSFQO-UHFFFAOYSA-N 0.000 description 1
- MFWUWIMILXOHQA-UHFFFAOYSA-N 2-amino-6-naphthalen-1-yl-1h-pyrimidin-4-one Chemical compound NC1=NC(O)=CC(C=2C3=CC=CC=C3C=CC=2)=N1 MFWUWIMILXOHQA-UHFFFAOYSA-N 0.000 description 1
- KXYGHDWFGFZJPJ-UHFFFAOYSA-N 2-amino-6-phenyl-1h-pyrimidin-4-one Chemical compound N1C(N)=NC(=O)C=C1C1=CC=CC=C1 KXYGHDWFGFZJPJ-UHFFFAOYSA-N 0.000 description 1
- MNIKKPHWWBUBCL-UHFFFAOYSA-N 2-amino-6-propan-2-yl-1h-pyrimidin-4-one Chemical compound CC(C)C1=CC(=O)N=C(N)N1 MNIKKPHWWBUBCL-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- MYHNUQVKTSTVDI-UHFFFAOYSA-N 2-methyl-2-[(2-methylpropan-2-yl)oxy]propane;potassium Chemical compound [K].CC(C)(C)OC(C)(C)C MYHNUQVKTSTVDI-UHFFFAOYSA-N 0.000 description 1
- WSBGKEVVRHNGOB-UHFFFAOYSA-N 2-methylsulfanyl-6-propan-2-yl-1h-pyrimidin-4-one Chemical compound CSC1=NC(=O)C=C(C(C)C)N1 WSBGKEVVRHNGOB-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- KEQVEUNVGHXXBY-UHFFFAOYSA-N 3-[6-(4-fluoronaphthalen-1-yl)-2-methylsulfanylpyrimidin-4-yl]propan-1-ol Chemical compound CSC1=NC(CCCO)=CC(C=2C3=CC=CC=C3C(F)=CC=2)=N1 KEQVEUNVGHXXBY-UHFFFAOYSA-N 0.000 description 1
- XRQNRXJXNXAYAI-UHFFFAOYSA-N 3-[6-(4-fluoronaphthalen-1-yl)-2-methylsulfonylpyrimidin-4-yl]propan-1-ol Chemical compound CS(=O)(=O)C1=NC(CCCO)=CC(C=2C3=CC=CC=C3C(F)=CC=2)=N1 XRQNRXJXNXAYAI-UHFFFAOYSA-N 0.000 description 1
- RUGFWNOTXBMCJB-UHFFFAOYSA-N 3b26 Chemical compound NC1=NC(C)=CC(C=2C=3C=CC=C4COCC(C=34)=CC=2)=N1 RUGFWNOTXBMCJB-UHFFFAOYSA-N 0.000 description 1
- FERBIZCKDIJEAV-UHFFFAOYSA-N 4,4-dimethyl-3-oxopentanoic acid Chemical compound CC(C)(C)C(=O)CC(O)=O FERBIZCKDIJEAV-UHFFFAOYSA-N 0.000 description 1
- NHVIQKCLFILTEE-UHFFFAOYSA-N 4,4-dimethylpentane-2,3-dione Chemical compound CC(=O)C(=O)C(C)(C)C NHVIQKCLFILTEE-UHFFFAOYSA-N 0.000 description 1
- XXWVGTLEQSGSIX-UHFFFAOYSA-N 4,5-dimethyl-6-naphthalen-1-ylpyrimidin-2-amine Chemical compound CC1=NC(N)=NC(C=2C3=CC=CC=C3C=CC=2)=C1C XXWVGTLEQSGSIX-UHFFFAOYSA-N 0.000 description 1
- DIVFRSHRFBPBDA-UHFFFAOYSA-N 4-(1,2-dihydroacenaphthylen-5-yl)-6-methylpyrimidin-2-amine Chemical compound NC1=NC(C)=CC(C=2C=3C=CC=C4CCC(C=34)=CC=2)=N1 DIVFRSHRFBPBDA-UHFFFAOYSA-N 0.000 description 1
- LIDSZINBVIJNQT-UHFFFAOYSA-N 4-(1,2-dihydroacenaphthylen-5-yl)-6-propan-2-ylpyrimidin-2-amine Chemical compound NC1=NC(C(C)C)=CC(C=2C=3C=CC=C4CCC(C=34)=CC=2)=N1 LIDSZINBVIJNQT-UHFFFAOYSA-N 0.000 description 1
- IEYXYKBZJHPKGV-UHFFFAOYSA-N 4-(1-methylindol-3-yl)pyrimidin-2-amine Chemical compound C12=CC=CC=C2N(C)C=C1C1=CC=NC(N)=N1 IEYXYKBZJHPKGV-UHFFFAOYSA-N 0.000 description 1
- OKBNSEOEQHFAQN-UHFFFAOYSA-N 4-(1-methylindol-3-yl)pyrimidin-2-amine;hydrochloride Chemical compound Cl.C12=CC=CC=C2N(C)C=C1C1=CC=NC(N)=N1 OKBNSEOEQHFAQN-UHFFFAOYSA-N 0.000 description 1
- BIJQXSOIHATDQO-UHFFFAOYSA-N 4-(1-methylindol-4-yl)-6-propan-2-ylpyrimidin-2-amine Chemical compound NC1=NC(C(C)C)=CC(C=2C=3C=CN(C)C=3C=CC=2)=N1 BIJQXSOIHATDQO-UHFFFAOYSA-N 0.000 description 1
- ACUIAAQWMVNEPO-UHFFFAOYSA-N 4-(1h-indol-4-yl)-6-propan-2-ylpyrimidin-2-amine Chemical compound NC1=NC(C(C)C)=CC(C=2C=3C=CNC=3C=CC=2)=N1 ACUIAAQWMVNEPO-UHFFFAOYSA-N 0.000 description 1
- STPANQHQLRYCQM-UHFFFAOYSA-N 4-(1h-indol-4-yl)-6-propan-2-ylpyrimidin-2-amine;hydrochloride Chemical compound Cl.NC1=NC(C(C)C)=CC(C=2C=3C=CNC=3C=CC=2)=N1 STPANQHQLRYCQM-UHFFFAOYSA-N 0.000 description 1
- ZWEVYLNWOOKOCP-UHFFFAOYSA-N 4-(1h-indol-7-yl)-6-propan-2-ylpyrimidin-2-amine Chemical compound NC1=NC(C(C)C)=CC(C=2C=3NC=CC=3C=CC=2)=N1 ZWEVYLNWOOKOCP-UHFFFAOYSA-N 0.000 description 1
- WWKTUEZALRKFIU-UHFFFAOYSA-N 4-(2,3-dihydro-1,4-benzodioxin-5-yl)-6-methylpyrimidin-2-amine;hydrochloride Chemical compound Cl.NC1=NC(C)=CC(C=2C=3OCCOC=3C=CC=2)=N1 WWKTUEZALRKFIU-UHFFFAOYSA-N 0.000 description 1
- XSDZBXTUUZHBOA-UHFFFAOYSA-N 4-(2,3-dihydro-1,4-benzoxazin-4-yl)-6-methylpyrimidin-2-amine Chemical compound NC1=NC(C)=CC(N2C3=CC=CC=C3OCC2)=N1 XSDZBXTUUZHBOA-UHFFFAOYSA-N 0.000 description 1
- UCFWAXMQWSZNGE-UHFFFAOYSA-N 4-(2,3-dihydroindol-1-yl)-6-methylpyrimidin-2-amine Chemical compound NC1=NC(C)=CC(N2C3=CC=CC=C3CC2)=N1 UCFWAXMQWSZNGE-UHFFFAOYSA-N 0.000 description 1
- BCLPXSMPLNOGAW-UHFFFAOYSA-N 4-(2-fluoronaphthalen-1-yl)-6-methoxypyrimidin-2-amine;hydrochloride Chemical compound Cl.NC1=NC(OC)=CC(C=2C3=CC=CC=C3C=CC=2F)=N1 BCLPXSMPLNOGAW-UHFFFAOYSA-N 0.000 description 1
- VSDSJFGLNMJQQU-UHFFFAOYSA-N 4-(2-fluoronaphthalen-1-yl)-6-methylpyrimidin-2-amine Chemical compound NC1=NC(C)=CC(C=2C3=CC=CC=C3C=CC=2F)=N1 VSDSJFGLNMJQQU-UHFFFAOYSA-N 0.000 description 1
- DGCCJJKGLLIZAG-UHFFFAOYSA-N 4-(2-fluoronaphthalen-1-yl)-6-propan-2-ylpyrimidin-2-amine;hydrochloride Chemical compound Cl.NC1=NC(C(C)C)=CC(C=2C3=CC=CC=C3C=CC=2F)=N1 DGCCJJKGLLIZAG-UHFFFAOYSA-N 0.000 description 1
- ZGHSMPRBKFXXIZ-UHFFFAOYSA-N 4-(2-methylnaphthalen-1-yl)-6-propan-2-ylpyrimidin-2-amine;hydrochloride Chemical compound Cl.NC1=NC(C(C)C)=CC(C=2C3=CC=CC=C3C=CC=2C)=N1 ZGHSMPRBKFXXIZ-UHFFFAOYSA-N 0.000 description 1
- ZBLPQZYDBZOSGT-UHFFFAOYSA-N 4-(2-methylpropyl)-6-naphthalen-1-ylpyrimidin-2-amine;hydrobromide Chemical compound Br.NC1=NC(CC(C)C)=CC(C=2C3=CC=CC=C3C=CC=2)=N1 ZBLPQZYDBZOSGT-UHFFFAOYSA-N 0.000 description 1
- CXDJBRFHLLEDMC-UHFFFAOYSA-N 4-(3,4-dihydro-1h-isoquinolin-2-yl)-6-methylpyrimidin-2-amine Chemical compound NC1=NC(C)=CC(N2CC3=CC=CC=C3CC2)=N1 CXDJBRFHLLEDMC-UHFFFAOYSA-N 0.000 description 1
- OFTWSLXJTOUEFU-UHFFFAOYSA-N 4-(3,4-dihydro-2h-quinolin-1-yl)-6-(trifluoromethyl)pyrimidin-2-amine Chemical compound FC(F)(F)C1=NC(N)=NC(N2C3=CC=CC=C3CCC2)=C1 OFTWSLXJTOUEFU-UHFFFAOYSA-N 0.000 description 1
- MIPSVTULDDWJBZ-UHFFFAOYSA-N 4-(3,4-dihydro-2h-quinolin-1-yl)-6-ethylpyrimidin-2-amine Chemical compound NC1=NC(CC)=CC(N2C3=CC=CC=C3CCC2)=N1 MIPSVTULDDWJBZ-UHFFFAOYSA-N 0.000 description 1
- KZACYKKYHBUKIE-UHFFFAOYSA-N 4-(3,4-dihydro-2h-quinolin-1-yl)-n,6-dimethylpyrimidin-2-amine Chemical compound CNC1=NC(C)=CC(N2C3=CC=CC=C3CCC2)=N1 KZACYKKYHBUKIE-UHFFFAOYSA-N 0.000 description 1
- QWYJHNHWIAQPSJ-UHFFFAOYSA-N 4-(3,4-dihydro-2h-quinolin-1-yl)-n-methylpyrimidin-2-amine Chemical compound CNC1=NC=CC(N2C3=CC=CC=C3CCC2)=N1 QWYJHNHWIAQPSJ-UHFFFAOYSA-N 0.000 description 1
- AAGKYOTZZAIIMH-UHFFFAOYSA-N 4-(3,5-dichlorophenyl)-6-methylpyrimidin-2-amine Chemical compound NC1=NC(C)=CC(C=2C=C(Cl)C=C(Cl)C=2)=N1 AAGKYOTZZAIIMH-UHFFFAOYSA-N 0.000 description 1
- RYTVESNWTAHIJY-UHFFFAOYSA-N 4-(3-chloro-4-fluorophenyl)-6-methylpyrimidin-2-amine Chemical compound NC1=NC(C)=CC(C=2C=C(Cl)C(F)=CC=2)=N1 RYTVESNWTAHIJY-UHFFFAOYSA-N 0.000 description 1
- SYIPUQPKWXTSFH-UHFFFAOYSA-N 4-(3-chlorophenyl)-6-methylpyrimidin-2-amine Chemical compound NC1=NC(C)=CC(C=2C=C(Cl)C=CC=2)=N1 SYIPUQPKWXTSFH-UHFFFAOYSA-N 0.000 description 1
- XTRZVZBNXXMLNW-UHFFFAOYSA-N 4-(3-fluorophenyl)-6-methylpyrimidin-2-amine Chemical compound NC1=NC(C)=CC(C=2C=C(F)C=CC=2)=N1 XTRZVZBNXXMLNW-UHFFFAOYSA-N 0.000 description 1
- DDXRJCJHXIUZJE-UHFFFAOYSA-N 4-(3-methoxyphenyl)-6-methylpyrimidin-2-amine Chemical compound COC1=CC=CC(C=2N=C(N)N=C(C)C=2)=C1 DDXRJCJHXIUZJE-UHFFFAOYSA-N 0.000 description 1
- HNZGDWADTCRIDT-UHFFFAOYSA-N 4-(3-methylbutyl)-6-naphthalen-1-ylpyrimidin-2-amine;hydrochloride Chemical compound Cl.NC1=NC(CCC(C)C)=CC(C=2C3=CC=CC=C3C=CC=2)=N1 HNZGDWADTCRIDT-UHFFFAOYSA-N 0.000 description 1
- ZDTMTDCREZWEHR-UHFFFAOYSA-N 4-(4,5-difluoronaphthalen-1-yl)-6-methylpyrimidin-2-amine Chemical compound NC1=NC(C)=CC(C=2C3=CC=CC(F)=C3C(F)=CC=2)=N1 ZDTMTDCREZWEHR-UHFFFAOYSA-N 0.000 description 1
- WSKFJTKFQWJTMB-UHFFFAOYSA-N 4-(4,5-difluoronaphthalen-1-yl)-6-propan-2-ylpyrimidin-2-amine Chemical compound NC1=NC(C(C)C)=CC(C=2C3=CC=CC(F)=C3C(F)=CC=2)=N1 WSKFJTKFQWJTMB-UHFFFAOYSA-N 0.000 description 1
- KUMXFFUVCXHLRY-UHFFFAOYSA-N 4-(4,5-dimethylnaphthalen-1-yl)-6-methylpyrimidin-2-amine Chemical compound NC1=NC(C)=CC(C=2C3=CC=CC(C)=C3C(C)=CC=2)=N1 KUMXFFUVCXHLRY-UHFFFAOYSA-N 0.000 description 1
- VAPHXLIRGTXAES-UHFFFAOYSA-N 4-(4,6-difluoronaphthalen-1-yl)-6-(2-fluoropropan-2-yl)pyrimidin-2-amine;hydrochloride Chemical compound Cl.NC1=NC(C(C)(F)C)=CC(C=2C3=CC=C(F)C=C3C(F)=CC=2)=N1 VAPHXLIRGTXAES-UHFFFAOYSA-N 0.000 description 1
- DRZJJAGSEYKASE-UHFFFAOYSA-N 4-(4,6-difluoronaphthalen-1-yl)-6-propan-2-ylpyrimidin-2-amine;hydrochloride Chemical compound Cl.NC1=NC(C(C)C)=CC(C=2C3=CC=C(F)C=C3C(F)=CC=2)=N1 DRZJJAGSEYKASE-UHFFFAOYSA-N 0.000 description 1
- RWPASRCPAGWVJC-UHFFFAOYSA-N 4-(4,7-difluoronaphthalen-1-yl)-6-propan-2-ylpyrimidin-2-amine Chemical compound NC1=NC(C(C)C)=CC(C=2C3=CC(F)=CC=C3C(F)=CC=2)=N1 RWPASRCPAGWVJC-UHFFFAOYSA-N 0.000 description 1
- ZUCRUXYPOADZNL-UHFFFAOYSA-N 4-(4,8-difluoronaphthalen-1-yl)-6-propan-2-ylpyrimidin-2-amine;hydrochloride Chemical compound Cl.NC1=NC(C(C)C)=CC(C=2C3=C(F)C=CC=C3C(F)=CC=2)=N1 ZUCRUXYPOADZNL-UHFFFAOYSA-N 0.000 description 1
- OKJUKBLPXSURMA-UHFFFAOYSA-N 4-(4-amino-5-chloro-2-methoxyphenyl)-6-methylpyrimidin-2-amine Chemical compound COC1=CC(N)=C(Cl)C=C1C1=CC(C)=NC(N)=N1 OKJUKBLPXSURMA-UHFFFAOYSA-N 0.000 description 1
- RISGNPLNRFSVQP-UHFFFAOYSA-N 4-(4-amino-5-chloro-2-methoxyphenyl)-6-propan-2-ylpyrimidin-2-amine;hydrochloride Chemical compound Cl.COC1=CC(N)=C(Cl)C=C1C1=CC(C(C)C)=NC(N)=N1 RISGNPLNRFSVQP-UHFFFAOYSA-N 0.000 description 1
- PZNFENFFHWBCKY-UHFFFAOYSA-N 4-(4-chloronaphthalen-1-yl)-6-(2-methylpropyl)pyrimidin-2-amine;hydrochloride Chemical compound Cl.NC1=NC(CC(C)C)=CC(C=2C3=CC=CC=C3C(Cl)=CC=2)=N1 PZNFENFFHWBCKY-UHFFFAOYSA-N 0.000 description 1
- VAZBGHGWXLKGQE-UHFFFAOYSA-N 4-(4-chloronaphthalen-1-yl)-6-ethylpyrimidin-2-amine Chemical compound NC1=NC(CC)=CC(C=2C3=CC=CC=C3C(Cl)=CC=2)=N1 VAZBGHGWXLKGQE-UHFFFAOYSA-N 0.000 description 1
- BXTKJHPCQTUBHI-UHFFFAOYSA-N 4-(4-chloronaphthalen-1-yl)-6-propan-2-ylpyrimidin-2-amine;hydrochloride Chemical compound Cl.NC1=NC(C(C)C)=CC(C=2C3=CC=CC=C3C(Cl)=CC=2)=N1 BXTKJHPCQTUBHI-UHFFFAOYSA-N 0.000 description 1
- DMJHDSXWMIJQOD-UHFFFAOYSA-N 4-(4-fluoronaphthalen-1-yl)-2-methylsulfanyl-6-propan-2-ylpyrimidine Chemical compound CSC1=NC(C(C)C)=CC(C=2C3=CC=CC=C3C(F)=CC=2)=N1 DMJHDSXWMIJQOD-UHFFFAOYSA-N 0.000 description 1
- MKRACAJQEAFJOU-UHFFFAOYSA-N 4-(4-fluoronaphthalen-1-yl)-2-methylsulfonyl-6-(2-phenylethyl)pyrimidine Chemical compound C=1C(C=2C3=CC=CC=C3C(F)=CC=2)=NC(S(=O)(=O)C)=NC=1CCC1=CC=CC=C1 MKRACAJQEAFJOU-UHFFFAOYSA-N 0.000 description 1
- CFYJSARWUOLCGA-UHFFFAOYSA-N 4-(4-fluoronaphthalen-1-yl)-2-piperidin-1-yl-6-propan-2-ylpyrimidine Chemical compound N=1C(C(C)C)=CC(C=2C3=CC=CC=C3C(F)=CC=2)=NC=1N1CCCCC1 CFYJSARWUOLCGA-UHFFFAOYSA-N 0.000 description 1
- SBXUULJWTVAYDS-UHFFFAOYSA-N 4-(4-fluoronaphthalen-1-yl)-6-(2,2,2-trifluoroethoxy)pyrimidin-2-amine;hydrochloride Chemical compound Cl.NC1=NC(OCC(F)(F)F)=CC(C=2C3=CC=CC=C3C(F)=CC=2)=N1 SBXUULJWTVAYDS-UHFFFAOYSA-N 0.000 description 1
- MQOFTAOPSKIECE-UHFFFAOYSA-N 4-(4-fluoronaphthalen-1-yl)-6-(2-fluoropropan-2-yl)-n-methylpyrimidin-2-amine Chemical compound CC(F)(C)C1=NC(NC)=NC(C=2C3=CC=CC=C3C(F)=CC=2)=C1 MQOFTAOPSKIECE-UHFFFAOYSA-N 0.000 description 1
- CJKIGMZOZHDVNA-UHFFFAOYSA-N 4-(4-fluoronaphthalen-1-yl)-6-(2-fluoropropan-2-yl)pyrimidin-2-amine;hydrochloride Chemical compound Cl.NC1=NC(C(C)(F)C)=CC(C=2C3=CC=CC=C3C(F)=CC=2)=N1 CJKIGMZOZHDVNA-UHFFFAOYSA-N 0.000 description 1
- RNIOMBQCSFQCNZ-UHFFFAOYSA-N 4-(4-fluoronaphthalen-1-yl)-6-(2-methylpropyl)pyrimidin-2-amine;hydrochloride Chemical compound Cl.NC1=NC(CC(C)C)=CC(C=2C3=CC=CC=C3C(F)=CC=2)=N1 RNIOMBQCSFQCNZ-UHFFFAOYSA-N 0.000 description 1
- UWMWJUPFRNPCEL-UHFFFAOYSA-N 4-(4-fluoronaphthalen-1-yl)-6-(3,3,3-trifluoropropyl)pyrimidin-2-amine;hydrochloride Chemical compound Cl.NC1=NC(CCC(F)(F)F)=CC(C=2C3=CC=CC=C3C(F)=CC=2)=N1 UWMWJUPFRNPCEL-UHFFFAOYSA-N 0.000 description 1
- QVKVYEBOZJNAMP-UHFFFAOYSA-N 4-(4-fluoronaphthalen-1-yl)-6-methoxy-2-methylsulfanylpyrimidine Chemical compound CSC1=NC(OC)=CC(C=2C3=CC=CC=C3C(F)=CC=2)=N1 QVKVYEBOZJNAMP-UHFFFAOYSA-N 0.000 description 1
- XXZCXOGRJPZJMG-UHFFFAOYSA-N 4-(4-fluoronaphthalen-1-yl)-6-methoxy-2-methylsulfonylpyrimidine Chemical compound CS(=O)(=O)C1=NC(OC)=CC(C=2C3=CC=CC=C3C(F)=CC=2)=N1 XXZCXOGRJPZJMG-UHFFFAOYSA-N 0.000 description 1
- GDAWHEKVXSSWNO-UHFFFAOYSA-N 4-(4-fluoronaphthalen-1-yl)-6-methoxy-n-propan-2-ylpyrimidin-2-amine;hydrochloride Chemical compound Cl.CC(C)NC1=NC(OC)=CC(C=2C3=CC=CC=C3C(F)=CC=2)=N1 GDAWHEKVXSSWNO-UHFFFAOYSA-N 0.000 description 1
- UGTQCUXMPGITRA-UHFFFAOYSA-N 4-(4-fluoronaphthalen-1-yl)-6-methoxypyrimidin-2-amine;hydrochloride Chemical compound Cl.NC1=NC(OC)=CC(C=2C3=CC=CC=C3C(F)=CC=2)=N1 UGTQCUXMPGITRA-UHFFFAOYSA-N 0.000 description 1
- GKHUHBABQGPOTO-UHFFFAOYSA-N 4-(4-fluoronaphthalen-1-yl)-6-methyl-2-methylsulfanylpyrimidine Chemical compound CSC1=NC(C)=CC(C=2C3=CC=CC=C3C(F)=CC=2)=N1 GKHUHBABQGPOTO-UHFFFAOYSA-N 0.000 description 1
- YNVJBUZVXHJAPA-UHFFFAOYSA-N 4-(4-fluoronaphthalen-1-yl)-6-methylpyrimidin-2-amine;hydrochloride Chemical compound Cl.NC1=NC(C)=CC(C=2C3=CC=CC=C3C(F)=CC=2)=N1 YNVJBUZVXHJAPA-UHFFFAOYSA-N 0.000 description 1
- FKGGZYLTBDTLOH-UHFFFAOYSA-N 4-(4-fluoronaphthalen-1-yl)-6-prop-1-en-2-ylpyrimidin-2-amine Chemical compound NC1=NC(C(=C)C)=CC(C=2C3=CC=CC=C3C(F)=CC=2)=N1 FKGGZYLTBDTLOH-UHFFFAOYSA-N 0.000 description 1
- TUFODHSWKBAKJV-UHFFFAOYSA-N 4-(4-fluoronaphthalen-1-yl)-6-propan-2-yl-n-propylpyrimidin-2-amine Chemical compound CCCNC1=NC(C(C)C)=CC(C=2C3=CC=CC=C3C(F)=CC=2)=N1 TUFODHSWKBAKJV-UHFFFAOYSA-N 0.000 description 1
- MKJPYBJBPRFMHL-UHFFFAOYSA-N 4-(4-fluoronaphthalen-1-yl)-6-propan-2-ylpyrimidin-2-amine;hydrochloride Chemical compound Cl.NC1=NC(C(C)C)=CC(C=2C3=CC=CC=C3C(F)=CC=2)=N1 MKJPYBJBPRFMHL-UHFFFAOYSA-N 0.000 description 1
- RBLSVBAMAVQRGF-UHFFFAOYSA-N 4-(4-fluoronaphthalen-1-yl)-6-propylpyrimidin-2-amine Chemical compound NC1=NC(CCC)=CC(C=2C3=CC=CC=C3C(F)=CC=2)=N1 RBLSVBAMAVQRGF-UHFFFAOYSA-N 0.000 description 1
- LNIMPKJIZBEXOB-UHFFFAOYSA-N 4-(4-fluoronaphthalen-1-yl)-n,n-dimethyl-6-propan-2-ylpyrimidin-2-amine Chemical compound CN(C)C1=NC(C(C)C)=CC(C=2C3=CC=CC=C3C(F)=CC=2)=N1 LNIMPKJIZBEXOB-UHFFFAOYSA-N 0.000 description 1
- XUELIXJORALAOB-UHFFFAOYSA-N 4-(4-fluoronaphthalen-1-yl)-n-(2-methoxyethyl)-6-propan-2-ylpyrimidin-2-amine Chemical compound COCCNC1=NC(C(C)C)=CC(C=2C3=CC=CC=C3C(F)=CC=2)=N1 XUELIXJORALAOB-UHFFFAOYSA-N 0.000 description 1
- LPNWWCWIOROGQC-UHFFFAOYSA-N 4-(4-fluoronaphthalen-1-yl)-n-methyl-6-(2-phenylethyl)pyrimidin-2-amine;hydrochloride Chemical compound Cl.C=1C(C=2C3=CC=CC=C3C(F)=CC=2)=NC(NC)=NC=1CCC1=CC=CC=C1 LPNWWCWIOROGQC-UHFFFAOYSA-N 0.000 description 1
- VRHQWCNMRVISGY-UHFFFAOYSA-N 4-(4-fluoronaphthalen-1-yl)pyrimidin-2-amine Chemical compound NC1=NC=CC(C=2C3=CC=CC=C3C(F)=CC=2)=N1 VRHQWCNMRVISGY-UHFFFAOYSA-N 0.000 description 1
- BPFUVCMPSXVJMB-UHFFFAOYSA-N 4-(4-methoxynaphthalen-1-yl)-6-methylpyrimidin-2-amine;hydrochloride Chemical compound Cl.C12=CC=CC=C2C(OC)=CC=C1C1=CC(C)=NC(N)=N1 BPFUVCMPSXVJMB-UHFFFAOYSA-N 0.000 description 1
- ONVYJGADLVLXGU-UHFFFAOYSA-N 4-(4-methoxynaphthalen-1-yl)-6-propan-2-ylpyrimidin-2-amine;hydrochloride Chemical compound Cl.C12=CC=CC=C2C(OC)=CC=C1C1=CC(C(C)C)=NC(N)=N1 ONVYJGADLVLXGU-UHFFFAOYSA-N 0.000 description 1
- IOQUKQGJRBGTBL-UHFFFAOYSA-N 4-(4-methylnaphthalen-1-yl)-6-propan-2-ylpyrimidin-2-amine Chemical compound NC1=NC(C(C)C)=CC(C=2C3=CC=CC=C3C(C)=CC=2)=N1 IOQUKQGJRBGTBL-UHFFFAOYSA-N 0.000 description 1
- BROZZROKXQWZDI-UHFFFAOYSA-N 4-(5-chlorothiophen-2-yl)-6-methylpyrimidin-2-amine Chemical compound NC1=NC(C)=CC(C=2SC(Cl)=CC=2)=N1 BROZZROKXQWZDI-UHFFFAOYSA-N 0.000 description 1
- NULDKYACSRNQSU-UHFFFAOYSA-N 4-(5-fluoronaphthalen-1-yl)-6-propan-2-ylpyrimidin-2-amine Chemical compound NC1=NC(C(C)C)=CC(C=2C3=CC=CC(F)=C3C=CC=2)=N1 NULDKYACSRNQSU-UHFFFAOYSA-N 0.000 description 1
- UVZUYLIXYOEXRK-UHFFFAOYSA-N 4-(6-fluoro-2-methyl-3,4-dihydro-2h-quinolin-1-yl)-6-methylpyrimidin-2-amine Chemical compound CC1CCC2=CC(F)=CC=C2N1C1=CC(C)=NC(N)=N1 UVZUYLIXYOEXRK-UHFFFAOYSA-N 0.000 description 1
- DMMVZOBFYNOHSU-UHFFFAOYSA-N 4-(6-fluoro-3,4-dihydro-2h-quinolin-1-yl)-6-methylpyrimidin-2-amine Chemical compound NC1=NC(C)=CC(N2C3=CC=C(F)C=C3CCC2)=N1 DMMVZOBFYNOHSU-UHFFFAOYSA-N 0.000 description 1
- LUJBZPPDTNMHRS-UHFFFAOYSA-N 4-(6-methoxy-3,4-dihydro-2h-quinolin-1-yl)-6-(trifluoromethyl)pyrimidin-2-amine Chemical compound C1CCC2=CC(OC)=CC=C2N1C1=CC(C(F)(F)F)=NC(N)=N1 LUJBZPPDTNMHRS-UHFFFAOYSA-N 0.000 description 1
- CQFMMZZTKSAUBK-UHFFFAOYSA-N 4-(6-methoxy-3,4-dihydro-2h-quinolin-1-yl)-6-methylpyrimidin-2-amine Chemical compound C1CCC2=CC(OC)=CC=C2N1C1=CC(C)=NC(N)=N1 CQFMMZZTKSAUBK-UHFFFAOYSA-N 0.000 description 1
- PMNKRFVAQJAVHJ-UHFFFAOYSA-N 4-(cyclopropylmethyl)-6-(4-fluoronaphthalen-1-yl)pyrimidin-2-amine;hydrochloride Chemical compound Cl.C=1C(C=2C3=CC=CC=C3C(F)=CC=2)=NC(N)=NC=1CC1CC1 PMNKRFVAQJAVHJ-UHFFFAOYSA-N 0.000 description 1
- RHVVGSFCNJIFKM-UHFFFAOYSA-N 4-[4-(4-fluoronaphthalen-1-yl)-6-propan-2-ylpyrimidin-2-yl]morpholine Chemical compound N=1C(C(C)C)=CC(C=2C3=CC=CC=C3C(F)=CC=2)=NC=1N1CCOCC1 RHVVGSFCNJIFKM-UHFFFAOYSA-N 0.000 description 1
- GBXGVYIWNLITRR-UHFFFAOYSA-N 4-benzyl-6-chloropyrimidin-2-amine Chemical compound NC1=NC(Cl)=CC(CC=2C=CC=CC=2)=N1 GBXGVYIWNLITRR-UHFFFAOYSA-N 0.000 description 1
- YAVKPQQKMFTDCU-UHFFFAOYSA-N 4-benzyl-6-naphthalen-1-ylpyrimidin-2-amine Chemical compound C=1C(C=2C3=CC=CC=C3C=CC=2)=NC(N)=NC=1CC1=CC=CC=C1 YAVKPQQKMFTDCU-UHFFFAOYSA-N 0.000 description 1
- AFXNWQFEFRRIMP-UHFFFAOYSA-N 4-butan-2-yl-6-chloropyrimidin-2-amine Chemical compound CCC(C)C1=CC(Cl)=NC(N)=N1 AFXNWQFEFRRIMP-UHFFFAOYSA-N 0.000 description 1
- JIXUXKOOTPBQIX-UHFFFAOYSA-N 4-butan-2-yl-6-naphthalen-1-ylpyrimidin-2-amine Chemical compound NC1=NC(C(C)CC)=CC(C=2C3=CC=CC=C3C=CC=2)=N1 JIXUXKOOTPBQIX-UHFFFAOYSA-N 0.000 description 1
- DFOHHQRGDOQMKG-UHFFFAOYSA-N 4-chloro-2-methylsulfanylpyrimidine Chemical class CSC1=NC=CC(Cl)=N1 DFOHHQRGDOQMKG-UHFFFAOYSA-N 0.000 description 1
- JNCHETBCCQKKKD-UHFFFAOYSA-N 4-chloro-5-fluoro-6-methylpyrimidin-2-amine Chemical compound CC1=NC(N)=NC(Cl)=C1F JNCHETBCCQKKKD-UHFFFAOYSA-N 0.000 description 1
- NFKDWZUZRKWRID-UHFFFAOYSA-N 4-chloro-6-(cyclopropylmethyl)pyrimidin-2-amine Chemical compound NC1=NC(Cl)=CC(CC2CC2)=N1 NFKDWZUZRKWRID-UHFFFAOYSA-N 0.000 description 1
- ZLIUVGFJXHOHLN-UHFFFAOYSA-N 4-chloro-6-(trifluoromethyl)pyrimidin-2-amine Chemical compound NC1=NC(Cl)=CC(C(F)(F)F)=N1 ZLIUVGFJXHOHLN-UHFFFAOYSA-N 0.000 description 1
- FTXYFHWTPCLTMG-UHFFFAOYSA-N 4-chloro-6-cyclobutylpyrimidin-2-amine Chemical compound NC1=NC(Cl)=CC(C2CCC2)=N1 FTXYFHWTPCLTMG-UHFFFAOYSA-N 0.000 description 1
- NVORZYQMYNXTHJ-UHFFFAOYSA-N 4-chloro-6-cyclopentylpyrimidin-2-amine Chemical compound NC1=NC(Cl)=CC(C2CCCC2)=N1 NVORZYQMYNXTHJ-UHFFFAOYSA-N 0.000 description 1
- KXBBHTZHROZBCL-UHFFFAOYSA-N 4-chloro-6-cyclopropylpyrimidin-2-amine Chemical compound NC1=NC(Cl)=CC(C2CC2)=N1 KXBBHTZHROZBCL-UHFFFAOYSA-N 0.000 description 1
- GZOWPTJWHDWHPK-UHFFFAOYSA-N 4-chloro-6-ethylpyrimidin-2-amine Chemical compound CCC1=CC(Cl)=NC(N)=N1 GZOWPTJWHDWHPK-UHFFFAOYSA-N 0.000 description 1
- ALMBOXQFPLQVLF-UHFFFAOYSA-N 4-chloro-6-methyl-2-methylsulfanylpyrimidine Chemical compound CSC1=NC(C)=CC(Cl)=N1 ALMBOXQFPLQVLF-UHFFFAOYSA-N 0.000 description 1
- ALUBSZGHFDXJIU-UHFFFAOYSA-N 4-chloro-6-naphthalen-1-ylpyrimidin-2-amine Chemical compound NC1=NC(Cl)=CC(C=2C3=CC=CC=C3C=CC=2)=N1 ALUBSZGHFDXJIU-UHFFFAOYSA-N 0.000 description 1
- INLQPZCEQRTUEB-UHFFFAOYSA-N 4-chloro-6-naphthalen-1-ylpyrimidin-2-amine;hydrochloride Chemical compound Cl.NC1=NC(Cl)=CC(C=2C3=CC=CC=C3C=CC=2)=N1 INLQPZCEQRTUEB-UHFFFAOYSA-N 0.000 description 1
- FIPBRZXDWSODDX-UHFFFAOYSA-N 4-chloro-6-phenylpyrimidin-2-amine Chemical compound NC1=NC(Cl)=CC(C=2C=CC=CC=2)=N1 FIPBRZXDWSODDX-UHFFFAOYSA-N 0.000 description 1
- SPMMDFHRMVXLLO-UHFFFAOYSA-N 4-chloro-6-propan-2-ylpyrimidin-2-amine Chemical compound CC(C)C1=CC(Cl)=NC(N)=N1 SPMMDFHRMVXLLO-UHFFFAOYSA-N 0.000 description 1
- HBTAOSGHCXUEKI-UHFFFAOYSA-N 4-chloro-n,n-dimethyl-3-nitrobenzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 HBTAOSGHCXUEKI-UHFFFAOYSA-N 0.000 description 1
- DYCAIWGKCFWOGZ-UHFFFAOYSA-N 4-cyclobutyl-6-(1h-indol-4-yl)pyrimidin-2-amine Chemical compound C=1C(C=2C=3C=CNC=3C=CC=2)=NC(N)=NC=1C1CCC1 DYCAIWGKCFWOGZ-UHFFFAOYSA-N 0.000 description 1
- XZIHQHKICMTKHI-UHFFFAOYSA-N 4-cyclobutyl-6-(4-fluoronaphthalen-1-yl)pyrimidin-2-amine;hydrochloride Chemical compound Cl.C=1C(C=2C3=CC=CC=C3C(F)=CC=2)=NC(N)=NC=1C1CCC1 XZIHQHKICMTKHI-UHFFFAOYSA-N 0.000 description 1
- MNRDBFJSRMUZIM-UHFFFAOYSA-N 4-cyclobutyl-6-naphthalen-1-ylpyrimidin-2-amine Chemical compound C=1C(C=2C3=CC=CC=C3C=CC=2)=NC(N)=NC=1C1CCC1 MNRDBFJSRMUZIM-UHFFFAOYSA-N 0.000 description 1
- QKMQXMSGAXVVHD-UHFFFAOYSA-N 4-cyclopentyl-6-naphthalen-1-ylpyrimidin-2-amine Chemical compound C=1C(C=2C3=CC=CC=C3C=CC=2)=NC(N)=NC=1C1CCCC1 QKMQXMSGAXVVHD-UHFFFAOYSA-N 0.000 description 1
- VBMKKIWHILFPRO-UHFFFAOYSA-N 4-cyclopropyl-6-(1h-indol-4-yl)pyrimidin-2-amine;hydrochloride Chemical compound Cl.C=1C(C=2C=3C=CNC=3C=CC=2)=NC(N)=NC=1C1CC1 VBMKKIWHILFPRO-UHFFFAOYSA-N 0.000 description 1
- XCZRWDSFZABUSE-UHFFFAOYSA-N 4-cyclopropyl-6-(4-fluoronaphthalen-1-yl)pyrimidin-2-amine Chemical compound C=1C(C=2C3=CC=CC=C3C(F)=CC=2)=NC(N)=NC=1C1CC1 XCZRWDSFZABUSE-UHFFFAOYSA-N 0.000 description 1
- UAXZQANQEVTDNV-UHFFFAOYSA-N 4-cyclopropyl-6-naphthalen-1-ylpyrimidin-2-amine Chemical compound C=1C(C=2C3=CC=CC=C3C=CC=2)=NC(N)=NC=1C1CC1 UAXZQANQEVTDNV-UHFFFAOYSA-N 0.000 description 1
- VIXSJLPMIMBUAZ-UHFFFAOYSA-N 4-ethoxy-6-naphthalen-1-ylpyrimidin-2-amine;hydrochloride Chemical compound Cl.NC1=NC(OCC)=CC(C=2C3=CC=CC=C3C=CC=2)=N1 VIXSJLPMIMBUAZ-UHFFFAOYSA-N 0.000 description 1
- QGTQGVIBXMIART-UHFFFAOYSA-N 4-ethyl-6-(4-fluoro-2-methylnaphthalen-1-yl)pyrimidin-2-amine Chemical compound NC1=NC(CC)=CC(C=2C3=CC=CC=C3C(F)=CC=2C)=N1 QGTQGVIBXMIART-UHFFFAOYSA-N 0.000 description 1
- LPGLFCWOONFBTJ-UHFFFAOYSA-N 4-ethyl-6-(4-fluoronaphthalen-1-yl)pyrimidin-2-amine;hydrochloride Chemical compound Cl.NC1=NC(CC)=CC(C=2C3=CC=CC=C3C(F)=CC=2)=N1 LPGLFCWOONFBTJ-UHFFFAOYSA-N 0.000 description 1
- QNLJOIFBDUVMNF-UHFFFAOYSA-N 4-ethyl-6-(4-methoxynaphthalen-1-yl)pyrimidin-2-amine;hydrochloride Chemical compound Cl.NC1=NC(CC)=CC(C=2C3=CC=CC=C3C(OC)=CC=2)=N1 QNLJOIFBDUVMNF-UHFFFAOYSA-N 0.000 description 1
- XXZJIDFKVHCFQI-UHFFFAOYSA-N 4-ethyl-6-naphthalen-1-ylpyrimidin-2-amine;hydrochloride Chemical compound Cl.NC1=NC(CC)=CC(C=2C3=CC=CC=C3C=CC=2)=N1 XXZJIDFKVHCFQI-UHFFFAOYSA-N 0.000 description 1
- MJQPNBNWNAVSOY-UHFFFAOYSA-N 4-indol-1-yl-6-methylpyrimidin-2-amine;hydrochloride Chemical compound Cl.NC1=NC(C)=CC(N2C3=CC=CC=C3C=C2)=N1 MJQPNBNWNAVSOY-UHFFFAOYSA-N 0.000 description 1
- KHQTYHISWGFDNE-UHFFFAOYSA-N 4-isoquinolin-4-yl-6-methylpyrimidin-2-amine Chemical compound NC1=NC(C)=CC(C=2C3=CC=CC=C3C=NC=2)=N1 KHQTYHISWGFDNE-UHFFFAOYSA-N 0.000 description 1
- SLSGBPZTXFHUEC-UHFFFAOYSA-N 4-methoxy-6-naphthalen-1-ylpyrimidin-2-amine Chemical compound NC1=NC(OC)=CC(C=2C3=CC=CC=C3C=CC=2)=N1 SLSGBPZTXFHUEC-UHFFFAOYSA-N 0.000 description 1
- FJRFBIPFJRPRFC-UHFFFAOYSA-N 4-methoxy-6-naphthalen-1-ylpyrimidin-2-amine;hydrochloride Chemical compound Cl.NC1=NC(OC)=CC(C=2C3=CC=CC=C3C=CC=2)=N1 FJRFBIPFJRPRFC-UHFFFAOYSA-N 0.000 description 1
- KGVFDSPNCNBXBP-UHFFFAOYSA-N 4-methyl-4-naphthalen-1-yl-1h-pyrimidin-2-amine Chemical group C=1C=CC2=CC=CC=C2C=1C1(C)NC(N)=NC=C1 KGVFDSPNCNBXBP-UHFFFAOYSA-N 0.000 description 1
- ASSUDRYOLXAZAY-UHFFFAOYSA-N 4-methyl-6-(2,3,4,5-tetrahydro-1-benzazepin-1-yl)pyrimidin-2-amine Chemical compound NC1=NC(C)=CC(N2C3=CC=CC=C3CCCC2)=N1 ASSUDRYOLXAZAY-UHFFFAOYSA-N 0.000 description 1
- CMAPFMTVNAQXEB-UHFFFAOYSA-N 4-methyl-6-(2-methyl-2,3-dihydroindol-1-yl)pyrimidin-2-amine Chemical compound CC1CC2=CC=CC=C2N1C1=CC(C)=NC(N)=N1 CMAPFMTVNAQXEB-UHFFFAOYSA-N 0.000 description 1
- HDMYLGKFVFJIDO-UHFFFAOYSA-N 4-methyl-6-(2-methyl-3,4-dihydro-2h-quinolin-1-yl)pyrimidin-2-amine Chemical compound CC1CCC2=CC=CC=C2N1C1=CC(C)=NC(N)=N1 HDMYLGKFVFJIDO-UHFFFAOYSA-N 0.000 description 1
- VXYZFXADUKSGAN-UHFFFAOYSA-N 4-methyl-6-(2-methylnaphthalen-1-yl)pyrimidin-2-amine;hydrochloride Chemical compound Cl.NC1=NC(C)=CC(C=2C3=CC=CC=C3C=CC=2C)=N1 VXYZFXADUKSGAN-UHFFFAOYSA-N 0.000 description 1
- QTDHQKONBXQHTJ-UHFFFAOYSA-N 4-methyl-6-(3-nitrophenyl)pyrimidin-2-amine Chemical compound NC1=NC(C)=CC(C=2C=C(C=CC=2)[N+]([O-])=O)=N1 QTDHQKONBXQHTJ-UHFFFAOYSA-N 0.000 description 1
- GLDKJERZXUXGTN-UHFFFAOYSA-N 4-methyl-6-(4-methylnaphthalen-1-yl)pyrimidin-2-amine Chemical compound NC1=NC(C)=CC(C=2C3=CC=CC=C3C(C)=CC=2)=N1 GLDKJERZXUXGTN-UHFFFAOYSA-N 0.000 description 1
- KMGQNWHTOMENAD-UHFFFAOYSA-N 4-methyl-6-(6-methyl-1,2-dihydroacenaphthylen-5-yl)pyrimidin-2-amine Chemical compound NC1=NC(C)=CC(C=2C=3C(C)=CC=C4CCC(C=34)=CC=2)=N1 KMGQNWHTOMENAD-UHFFFAOYSA-N 0.000 description 1
- GOWPJUZMHLOAAZ-UHFFFAOYSA-N 4-methyl-6-(6-methyl-3,4-dihydro-2h-quinolin-1-yl)pyrimidin-2-amine Chemical compound C1CCC2=CC(C)=CC=C2N1C1=CC(C)=NC(N)=N1 GOWPJUZMHLOAAZ-UHFFFAOYSA-N 0.000 description 1
- QDQZABMYZKDVOK-UHFFFAOYSA-N 4-methyl-6-[3-(trifluoromethyl)phenyl]pyrimidin-2-amine Chemical compound NC1=NC(C)=CC(C=2C=C(C=CC=2)C(F)(F)F)=N1 QDQZABMYZKDVOK-UHFFFAOYSA-N 0.000 description 1
- ZTZVEMADPTUZAS-UHFFFAOYSA-N 4-methyl-6-naphthalen-1-ylpyrimidin-2-amine;hydrochloride Chemical compound Cl.NC1=NC(C)=CC(C=2C3=CC=CC=C3C=CC=2)=N1 ZTZVEMADPTUZAS-UHFFFAOYSA-N 0.000 description 1
- HCMVDROSZBPIFD-UHFFFAOYSA-N 4-methyl-6-phenanthren-9-ylpyrimidin-2-amine Chemical compound NC1=NC(C)=CC(C=2C3=CC=CC=C3C3=CC=CC=C3C=2)=N1 HCMVDROSZBPIFD-UHFFFAOYSA-N 0.000 description 1
- WNPIYAOUGPWJKY-UHFFFAOYSA-N 4-methyl-6-quinolin-8-ylpyrimidin-2-amine Chemical compound NC1=NC(C)=CC(C=2C3=NC=CC=C3C=CC=2)=N1 WNPIYAOUGPWJKY-UHFFFAOYSA-N 0.000 description 1
- FKRYPWMGWKOREF-UHFFFAOYSA-N 4-methylsulfanyl-6-naphthalen-1-ylpyrimidin-2-amine Chemical compound NC1=NC(SC)=CC(C=2C3=CC=CC=C3C=CC=2)=N1 FKRYPWMGWKOREF-UHFFFAOYSA-N 0.000 description 1
- ZZENNUJXCHKABR-UHFFFAOYSA-N 4-methylsulfanyl-6-naphthalen-1-ylpyrimidin-2-amine;hydrochloride Chemical compound Cl.NC1=NC(SC)=CC(C=2C3=CC=CC=C3C=CC=2)=N1 ZZENNUJXCHKABR-UHFFFAOYSA-N 0.000 description 1
- FMYOAORXIFKSMD-UHFFFAOYSA-N 4-naphthalen-1-yl-6-(trifluoromethyl)pyrimidin-2-amine Chemical compound FC(F)(F)C1=NC(N)=NC(C=2C3=CC=CC=C3C=CC=2)=C1 FMYOAORXIFKSMD-UHFFFAOYSA-N 0.000 description 1
- FEZREYZPPJVHCO-UHFFFAOYSA-N 4-naphthalen-1-yl-6-phenylpyrimidin-2-amine;hydrochloride Chemical compound Cl.C=1C(C=2C3=CC=CC=C3C=CC=2)=NC(N)=NC=1C1=CC=CC=C1 FEZREYZPPJVHCO-UHFFFAOYSA-N 0.000 description 1
- GHZOSTWNIRLBOT-UHFFFAOYSA-N 4-naphthalen-1-yl-6-propan-2-yloxypyrimidin-2-amine;hydrochloride Chemical compound Cl.NC1=NC(OC(C)C)=CC(C=2C3=CC=CC=C3C=CC=2)=N1 GHZOSTWNIRLBOT-UHFFFAOYSA-N 0.000 description 1
- GQCIUQMVGGKKRF-UHFFFAOYSA-N 4-naphthalen-1-yl-6-propylpyrimidin-2-amine Chemical compound NC1=NC(CCC)=CC(C=2C3=CC=CC=C3C=CC=2)=N1 GQCIUQMVGGKKRF-UHFFFAOYSA-N 0.000 description 1
- GWDXAKCWBPZHCK-UHFFFAOYSA-N 4-naphthalen-1-ylpyrimidin-2-amine Chemical compound NC1=NC=CC(C=2C3=CC=CC=C3C=CC=2)=N1 GWDXAKCWBPZHCK-UHFFFAOYSA-N 0.000 description 1
- TYAPGKCLMZBNJJ-UHFFFAOYSA-N 4-naphthalen-1-ylpyrimidin-2-amine;hydrochloride Chemical compound Cl.NC1=NC=CC(C=2C3=CC=CC=C3C=CC=2)=N1 TYAPGKCLMZBNJJ-UHFFFAOYSA-N 0.000 description 1
- IEJNUJNFZSQNHZ-UHFFFAOYSA-N 4-tert-butyl-6-(2-fluoronaphthalen-1-yl)pyrimidin-2-amine;hydrochloride Chemical compound Cl.NC1=NC(C(C)(C)C)=CC(C=2C3=CC=CC=C3C=CC=2F)=N1 IEJNUJNFZSQNHZ-UHFFFAOYSA-N 0.000 description 1
- NPBXTAPOXNYAJF-UHFFFAOYSA-N 4-tert-butyl-6-(4-fluoronaphthalen-1-yl)-n-(2-methoxyethyl)pyrimidin-2-amine;hydrochloride Chemical compound Cl.CC(C)(C)C1=NC(NCCOC)=NC(C=2C3=CC=CC=C3C(F)=CC=2)=C1 NPBXTAPOXNYAJF-UHFFFAOYSA-N 0.000 description 1
- BSBMADKJPIAVNK-UHFFFAOYSA-N 4-tert-butyl-6-(4-fluoronaphthalen-1-yl)-n-methylpyrimidin-2-amine Chemical compound CC(C)(C)C1=NC(NC)=NC(C=2C3=CC=CC=C3C(F)=CC=2)=C1 BSBMADKJPIAVNK-UHFFFAOYSA-N 0.000 description 1
- ZVGCPAWSOBWIRC-UHFFFAOYSA-N 4-tert-butyl-6-(4-fluoronaphthalen-1-yl)-n-propan-2-ylpyrimidin-2-amine;hydrobromide Chemical compound Br.CC(C)(C)C1=NC(NC(C)C)=NC(C=2C3=CC=CC=C3C(F)=CC=2)=C1 ZVGCPAWSOBWIRC-UHFFFAOYSA-N 0.000 description 1
- ADMKZZBMPJTPPQ-UHFFFAOYSA-N 4-tert-butyl-6-(4-fluoronaphthalen-1-yl)pyrimidin-2-amine Chemical compound NC1=NC(C(C)(C)C)=CC(C=2C3=CC=CC=C3C(F)=CC=2)=N1 ADMKZZBMPJTPPQ-UHFFFAOYSA-N 0.000 description 1
- QKDSZUYFJLFXPX-UHFFFAOYSA-N 4-tert-butyl-6-(4-fluoronaphthalen-1-yl)pyrimidin-2-amine;hydrochloride Chemical compound Cl.NC1=NC(C(C)(C)C)=CC(C=2C3=CC=CC=C3C(F)=CC=2)=N1 QKDSZUYFJLFXPX-UHFFFAOYSA-N 0.000 description 1
- HGXWRFCGPKQHOJ-UHFFFAOYSA-N 4-tert-butyl-6-naphthalen-1-ylpyrimidin-2-amine Chemical compound NC1=NC(C(C)(C)C)=CC(C=2C3=CC=CC=C3C=CC=2)=N1 HGXWRFCGPKQHOJ-UHFFFAOYSA-N 0.000 description 1
- RSKIQGAFXPIXNA-UHFFFAOYSA-N 5-fluoro-4-methyl-6-naphthalen-1-ylpyrimidin-2-amine Chemical compound CC1=NC(N)=NC(C=2C3=CC=CC=C3C=CC=2)=C1F RSKIQGAFXPIXNA-UHFFFAOYSA-N 0.000 description 1
- 101710138091 5-hydroxytryptamine receptor 2A Proteins 0.000 description 1
- 102100036321 5-hydroxytryptamine receptor 2A Human genes 0.000 description 1
- YRHASMJEFJVWLZ-UHFFFAOYSA-N 6-(3,4-dihydro-2h-quinolin-1-yl)-4-n,4-n-diethylpyrimidine-2,4-diamine;hydrochloride Chemical compound Cl.NC1=NC(N(CC)CC)=CC(N2C3=CC=CC=C3CCC2)=N1 YRHASMJEFJVWLZ-UHFFFAOYSA-N 0.000 description 1
- MSSSYXSGYWYIML-UHFFFAOYSA-N 6-(3,4-dihydro-2h-quinolin-1-yl)-7h-purin-2-amine Chemical compound C1CCC2=CC=CC=C2N1C1=C(N=CN2)C2=NC(N)=N1 MSSSYXSGYWYIML-UHFFFAOYSA-N 0.000 description 1
- QJIUMVUZDYPQRT-UHFFFAOYSA-N 6-chloro-2,4-pyrimidinediamine Chemical compound NC1=CC(Cl)=NC(N)=N1 QJIUMVUZDYPQRT-UHFFFAOYSA-N 0.000 description 1
- AOFIYIGGFIWIFQ-UHFFFAOYSA-N 6-naphthalen-1-ylpyrimidine-2,4-diamine;hydrochloride Chemical compound Cl.NC1=NC(N)=CC(C=2C3=CC=CC=C3C=CC=2)=N1 AOFIYIGGFIWIFQ-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 1
- ORILYTVJVMAKLC-UHFFFAOYSA-N Adamantane Natural products C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- FOJGPQZLJTZUIP-UHFFFAOYSA-N ClC1=NC(=NC(=C1C)C1=CC=C(C=C1)OC)N Chemical compound ClC1=NC(=NC(=C1C)C1=CC=C(C=C1)OC)N FOJGPQZLJTZUIP-UHFFFAOYSA-N 0.000 description 1
- 108010056643 Corticotropin-Releasing Hormone Receptors Proteins 0.000 description 1
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 1
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 1
- GKKZMYDNDDMXSE-UHFFFAOYSA-N Ethyl 3-oxo-3-phenylpropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC=C1 GKKZMYDNDDMXSE-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 101000783617 Homo sapiens 5-hydroxytryptamine receptor 2A Proteins 0.000 description 1
- 101000761319 Homo sapiens 5-hydroxytryptamine receptor 2B Proteins 0.000 description 1
- 101000761348 Homo sapiens 5-hydroxytryptamine receptor 2C Proteins 0.000 description 1
- 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 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- 241001529936 Murinae Species 0.000 description 1
- KYNFSYDLIFPHFO-UHFFFAOYSA-N N-[4-(4-fluoronaphthalen-1-yl)-6-propan-2-ylpyrimidin-2-yl]-N',N'-dimethylethane-1,2-diamine hydrochloride Chemical compound Cl.CN(C)CCNC1=NC(C(C)C)=CC(C=2C3=CC=CC=C3C(F)=CC=2)=N1 KYNFSYDLIFPHFO-UHFFFAOYSA-N 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 101710171573 Primary amine oxidase Proteins 0.000 description 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
- 101000761350 Rattus norvegicus 5-hydroxytryptamine receptor 2C Proteins 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Chemical group 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N Valeric acid Natural products CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- LNGYNLRUATUIDB-UHFFFAOYSA-N [4-(4-fluoronaphthalen-1-yl)-6-propan-2-ylpyrimidin-2-yl]hydrazine;hydrochloride Chemical compound Cl.NNC1=NC(C(C)C)=CC(C=2C3=CC=CC=C3C(F)=CC=2)=N1 LNGYNLRUATUIDB-UHFFFAOYSA-N 0.000 description 1
- NWLPHUYQUUNBOZ-UHFFFAOYSA-N [8-(2-amino-6-methylpyrimidin-4-yl)naphthalen-1-yl]methanol Chemical compound NC1=NC(C)=CC(C=2C3=C(CO)C=CC=C3C=CC=2)=N1 NWLPHUYQUUNBOZ-UHFFFAOYSA-N 0.000 description 1
- JZLUWZPEJDRDEO-UHFFFAOYSA-N [N].C1=CN=CN=C1 Chemical group [N].C1=CN=CN=C1 JZLUWZPEJDRDEO-UHFFFAOYSA-N 0.000 description 1
- BGPHCHDMUFIZFY-UHFFFAOYSA-N [Na].N=1C(C(C)C)=CC(C=2C3=CC=CC=C3C(F)=CC=2)=NC=1NCC1CCCO1 Chemical compound [Na].N=1C(C(C)C)=CC(C=2C3=CC=CC=C3C(F)=CC=2)=NC=1NCC1CCCO1 BGPHCHDMUFIZFY-UHFFFAOYSA-N 0.000 description 1
- 229940022663 acetate Drugs 0.000 description 1
- 239000012345 acetylating agent Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000003044 adaptive effect Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 230000000338 anxiogenic effect Effects 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229960000686 benzalkonium chloride Drugs 0.000 description 1
- BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical compound C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 229960004926 chlorobutanol Drugs 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 210000002987 choroid plexus Anatomy 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000012059 conventional drug carrier Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000019788 craving Nutrition 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000006622 cycloheptylmethyl group Chemical group 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
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000006623 cyclooctylmethyl group Chemical group 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- ZHXTWWCDMUWMDI-UHFFFAOYSA-N dihydroxyboron Chemical compound O[B]O ZHXTWWCDMUWMDI-UHFFFAOYSA-N 0.000 description 1
- 229940031578 diisopropyl adipate Drugs 0.000 description 1
- VAWRKITUPUFMHV-UHFFFAOYSA-N dimethoxyborane Chemical compound COBOC VAWRKITUPUFMHV-UHFFFAOYSA-N 0.000 description 1
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 206010013663 drug dependence Diseases 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- CJRQQJKWNULSFQ-UHFFFAOYSA-N ethyl 2-fluoro-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)F CJRQQJKWNULSFQ-UHFFFAOYSA-N 0.000 description 1
- SHTFQLHOTAJQRJ-UHFFFAOYSA-N ethyl 2-fluoro-3-oxobutanoate Chemical compound CCOC(=O)C(F)C(C)=O SHTFQLHOTAJQRJ-UHFFFAOYSA-N 0.000 description 1
- FNENWZWNOPCZGK-UHFFFAOYSA-N ethyl 2-methyl-3-oxobutanoate Chemical compound CCOC(=O)C(C)C(C)=O FNENWZWNOPCZGK-UHFFFAOYSA-N 0.000 description 1
- HYHZQZSNOAJEPU-UHFFFAOYSA-N ethyl 3-cyclobutyl-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)C1CCC1 HYHZQZSNOAJEPU-UHFFFAOYSA-N 0.000 description 1
- MUDKQMLLCRJCEY-UHFFFAOYSA-N ethyl 3-cyclopentyl-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)C1CCCC1 MUDKQMLLCRJCEY-UHFFFAOYSA-N 0.000 description 1
- LFSVADABIDBSBV-UHFFFAOYSA-N ethyl 3-cyclopropyl-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)C1CC1 LFSVADABIDBSBV-UHFFFAOYSA-N 0.000 description 1
- JFWSFANXHXCJOY-UHFFFAOYSA-N ethyl 3-naphthalen-1-yl-3-oxopropanoate Chemical group C1=CC=C2C(C(=O)CC(=O)OCC)=CC=CC2=C1 JFWSFANXHXCJOY-UHFFFAOYSA-N 0.000 description 1
- KSMHHMZHHCZPSP-UHFFFAOYSA-N ethyl 3-oxo-4-phenylpentanoate Chemical compound CCOC(=O)CC(=O)C(C)C1=CC=CC=C1 KSMHHMZHHCZPSP-UHFFFAOYSA-N 0.000 description 1
- UDRCONFHWYGWFI-UHFFFAOYSA-N ethyl 3-oxopentanoate Chemical compound CCOC(=O)CC(=O)CC UDRCONFHWYGWFI-UHFFFAOYSA-N 0.000 description 1
- OCJKUQIPRNZDTK-UHFFFAOYSA-N ethyl 4,4,4-trifluoro-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)C(F)(F)F OCJKUQIPRNZDTK-UHFFFAOYSA-N 0.000 description 1
- KHIHEUAINZCGRS-UHFFFAOYSA-N ethyl 4-methyl-3-oxohexanoate Chemical compound CCOC(=O)CC(=O)C(C)CC KHIHEUAINZCGRS-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- PJMPHNIQZUBGLI-UHFFFAOYSA-N fentanyl Chemical compound C=1C=CC=CC=1N(C(=O)CC)C(CC1)CCN1CCC1=CC=CC=C1 PJMPHNIQZUBGLI-UHFFFAOYSA-N 0.000 description 1
- 229960002428 fentanyl Drugs 0.000 description 1
- 239000012894 fetal calf serum Substances 0.000 description 1
- 210000002950 fibroblast Anatomy 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000003349 gelling agent Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 102000053799 human HTR2B Human genes 0.000 description 1
- 102000045993 human HTR2C Human genes 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 206010021654 increased appetite Diseases 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 231100000567 intoxicating Toxicity 0.000 description 1
- 230000002673 intoxicating effect Effects 0.000 description 1
- 230000004410 intraocular pressure Effects 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000004254 isoquinolin-1-yl group Chemical group [H]C1=C([H])C2=C([H])C([H])=C([H])C([H])=C2C(*)=N1 0.000 description 1
- 125000004552 isoquinolin-4-yl group Chemical group C1=NC=C(C2=CC=CC=C12)* 0.000 description 1
- 150000002541 isothioureas Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000008297 liquid dosage form Substances 0.000 description 1
- 238000005567 liquid scintillation counting Methods 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 238000003819 low-pressure liquid chromatography Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- SDDKIZNHOCEXTF-UHFFFAOYSA-N methyl carbamimidothioate Chemical compound CSC(N)=N SDDKIZNHOCEXTF-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 210000004877 mucosa Anatomy 0.000 description 1
- NWPPKYKYYROCPI-UHFFFAOYSA-N n-[4-(4-fluoronaphthalen-1-yl)-6-propan-2-ylpyrimidin-2-yl]acetamide Chemical compound CC(=O)NC1=NC(C(C)C)=CC(C=2C3=CC=CC=C3C(F)=CC=2)=N1 NWPPKYKYYROCPI-UHFFFAOYSA-N 0.000 description 1
- OZOUGCUANMTACN-UHFFFAOYSA-N n-benzyl-4-(4-fluoronaphthalen-1-yl)-6-propan-2-ylpyrimidin-2-amine Chemical compound N=1C(C(C)C)=CC(C=2C3=CC=CC=C3C(F)=CC=2)=NC=1NCC1=CC=CC=C1 OZOUGCUANMTACN-UHFFFAOYSA-N 0.000 description 1
- MJINPVNXLYKDEI-UHFFFAOYSA-N n-butyl-4-(4-fluoronaphthalen-1-yl)-6-methylpyrimidin-2-amine;hydrochloride Chemical compound Cl.CCCCNC1=NC(C)=CC(C=2C3=CC=CC=C3C(F)=CC=2)=N1 MJINPVNXLYKDEI-UHFFFAOYSA-N 0.000 description 1
- BFXDRSVAEIOTIT-UHFFFAOYSA-N n-butyl-4-(4-fluoronaphthalen-1-yl)-6-propan-2-ylpyrimidin-2-amine Chemical compound CCCCNC1=NC(C(C)C)=CC(C=2C3=CC=CC=C3C(F)=CC=2)=N1 BFXDRSVAEIOTIT-UHFFFAOYSA-N 0.000 description 1
- WXOLDTAWLBHGHX-UHFFFAOYSA-N n-cyclopropyl-4-(4-fluoronaphthalen-1-yl)-6-propan-2-ylpyrimidin-2-amine Chemical compound N=1C(C(C)C)=CC(C=2C3=CC=CC=C3C(F)=CC=2)=NC=1NC1CC1 WXOLDTAWLBHGHX-UHFFFAOYSA-N 0.000 description 1
- SRRYSLFTFNJHGL-UHFFFAOYSA-N n-ethyl-4-(4-fluoronaphthalen-1-yl)-6-propan-2-ylpyrimidin-2-amine Chemical compound CCNC1=NC(C(C)C)=CC(C=2C3=CC=CC=C3C(F)=CC=2)=N1 SRRYSLFTFNJHGL-UHFFFAOYSA-N 0.000 description 1
- ICFWLGYCUXWLGI-UHFFFAOYSA-N n-ethylpyrimidin-2-amine Chemical compound CCNC1=NC=CC=N1 ICFWLGYCUXWLGI-UHFFFAOYSA-N 0.000 description 1
- 230000010807 negative regulation of binding Effects 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 229940100692 oral suspension Drugs 0.000 description 1
- 239000001301 oxygen Chemical group 0.000 description 1
- 239000006174 pH buffer Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000018052 penile erection Effects 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229940096826 phenylmercuric acetate Drugs 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000002953 phosphate buffered saline Substances 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229940068968 polysorbate 80 Drugs 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- IDXKTTNFXPPXJY-UHFFFAOYSA-N pyrimidin-1-ium;chloride Chemical compound Cl.C1=CN=CN=C1 IDXKTTNFXPPXJY-UHFFFAOYSA-N 0.000 description 1
- 125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 description 1
- 125000004549 quinolin-4-yl group Chemical group N1=CC=C(C2=CC=CC=C12)* 0.000 description 1
- 230000036385 rapid eye movement (rem) sleep Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000010956 selective crystallization Methods 0.000 description 1
- 239000008299 semisolid dosage form Substances 0.000 description 1
- 239000002400 serotonin 2A antagonist Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 230000003860 sleep quality Effects 0.000 description 1
- 230000004622 sleep time Effects 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 208000011117 substance-related disease Diseases 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 229940117013 triethanolamine oleate Drugs 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/32—Alcohol-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/32—Nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Addiction (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Anesthesiology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Nutrition Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US1821896P | 1996-05-23 | 1996-05-23 | |
US4037797P | 1997-03-10 | 1997-03-10 | |
PCT/EP1997/002454 WO1997044326A1 (en) | 1996-05-23 | 1997-05-14 | Aryl pyrimidine derivatives |
Publications (3)
Publication Number | Publication Date |
---|---|
NO985392D0 NO985392D0 (no) | 1998-11-19 |
NO985392L NO985392L (no) | 1999-01-25 |
NO311800B1 true NO311800B1 (no) | 2002-01-28 |
Family
ID=26690869
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO19985392A NO311800B1 (no) | 1996-05-23 | 1998-11-19 | Arylpyrimidinderivater |
Country Status (32)
Country | Link |
---|---|
US (1) | US5863924A (ru) |
EP (1) | EP0901474B1 (ru) |
JP (1) | JP2001525794A (ru) |
KR (1) | KR100518101B1 (ru) |
CN (1) | CN1109675C (ru) |
AR (1) | AR007253A1 (ru) |
AT (1) | ATE323682T1 (ru) |
AU (1) | AU725891B2 (ru) |
BR (1) | BR9709599A (ru) |
CA (1) | CA2255705A1 (ru) |
CO (1) | CO4950514A1 (ru) |
CZ (1) | CZ291849B6 (ru) |
DE (1) | DE69735712T2 (ru) |
DK (1) | DK0901474T3 (ru) |
ES (1) | ES2262178T3 (ru) |
HK (1) | HK1020345A1 (ru) |
HR (1) | HRP970275B1 (ru) |
HU (1) | HUP9901535A3 (ru) |
ID (1) | ID16969A (ru) |
IL (1) | IL127056A (ru) |
MA (1) | MA26431A1 (ru) |
MY (1) | MY119181A (ru) |
NO (1) | NO311800B1 (ru) |
NZ (1) | NZ332802A (ru) |
PT (1) | PT901474E (ru) |
RU (1) | RU2189976C2 (ru) |
SA (2) | SA97180191B1 (ru) |
TR (1) | TR199802391T2 (ru) |
TW (1) | TW440563B (ru) |
UY (1) | UY24560A1 (ru) |
WO (1) | WO1997044326A1 (ru) |
YU (1) | YU53298A (ru) |
Families Citing this family (86)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1012151B1 (en) * | 1997-09-02 | 2002-08-07 | Bristol-Myers Squibb Pharma Company | Heterocyclyl-substituted ring-fused pyridines and pyrimidines as corticotropin releasing hormone (crh) antagonists, useful for treating cns and stress-related disorders |
US6040315A (en) * | 1997-10-30 | 2000-03-21 | Day; Charles E. | Antacid co-polymer of guanidine and polyethylenimine |
DE19844291A1 (de) * | 1998-09-18 | 2000-03-23 | Schering Ag | Benzoxazin- und Benzothiazin-Derivate und deren Verwendung in Arzneimitteln |
GB9828511D0 (en) | 1998-12-24 | 1999-02-17 | Zeneca Ltd | Chemical compounds |
US6495558B1 (en) | 1999-01-22 | 2002-12-17 | Amgen Inc. | Kinase inhibitors |
EP1144390A2 (en) * | 1999-01-22 | 2001-10-17 | Amgen Inc., | Kinase inhibitors |
DK1057831T3 (da) * | 1999-05-26 | 2005-01-31 | Hoffmann La Roche | Fremgangsmåde til fremstilling af vinylpyrimidinderivater |
DE60005526T2 (de) * | 1999-07-30 | 2004-07-01 | Pharmagene Laboratories Ltd. | Verwendung von 2-amino-4-(4-fluoronaphth-1-yl)-6-isopropylpyrimidine zur behandlung von erkrankungen des magen-darm-traktes |
GB9919778D0 (en) | 1999-08-21 | 1999-10-27 | Zeneca Ltd | Chemical compounds |
PL355639A1 (en) | 1999-09-10 | 2004-05-04 | Merck & Co, Inc. | Tyrosine kinase inhibitors |
US7101869B2 (en) | 1999-11-30 | 2006-09-05 | Pfizer Inc. | 2,4-diaminopyrimidine compounds useful as immunosuppressants |
EP1261327B1 (en) * | 2000-02-25 | 2005-04-27 | F.Hoffmann-La Roche Ag | Adenosine receptor modulators |
GB0004890D0 (en) | 2000-03-01 | 2000-04-19 | Astrazeneca Uk Ltd | Chemical compounds |
GB0004887D0 (en) | 2000-03-01 | 2000-04-19 | Astrazeneca Uk Ltd | Chemical compounds |
GB0004886D0 (en) | 2000-03-01 | 2000-04-19 | Astrazeneca Uk Ltd | Chemical compounds |
GB0004888D0 (en) | 2000-03-01 | 2000-04-19 | Astrazeneca Uk Ltd | Chemical compounds |
GB0007371D0 (en) | 2000-03-28 | 2000-05-17 | Astrazeneca Uk Ltd | Chemical compounds |
GB0016877D0 (en) | 2000-07-11 | 2000-08-30 | Astrazeneca Ab | Chemical compounds |
GB0021726D0 (en) | 2000-09-05 | 2000-10-18 | Astrazeneca Ab | Chemical compounds |
US6444477B1 (en) | 2000-11-28 | 2002-09-03 | Pharmagene Laboratories Limited | Assay method for detecting 5-HT2B antagonists |
GB0103926D0 (en) | 2001-02-17 | 2001-04-04 | Astrazeneca Ab | Chemical compounds |
EE200300546A (et) * | 2001-05-14 | 2004-04-15 | Bristol-Myers Squibb Pharma Company | Asendatud pürasinoonid, püridiinid ja pürimidiinid kui kortikotropiini vabastava faktori ligandid |
GB0113041D0 (en) | 2001-05-30 | 2001-07-18 | Astrazeneca Ab | Chemical compounds |
WO2002102313A2 (en) * | 2001-06-19 | 2002-12-27 | Bristol-Myers Squibb Company | Pyrimidine inhibitors of phosphodiesterase (pde) 7 |
US6825198B2 (en) * | 2001-06-21 | 2004-11-30 | Pfizer Inc | 5-HT receptor ligands and uses thereof |
CA2450562A1 (en) | 2001-06-22 | 2003-01-03 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
TWI329105B (en) | 2002-02-01 | 2010-08-21 | Rigel Pharmaceuticals Inc | 2,4-pyrimidinediamine compounds and their uses |
EP1474141A1 (en) * | 2002-02-13 | 2004-11-10 | Pharmagene Laboratories Ltd | 5-ht2b receptor antagonists |
GB0203412D0 (en) * | 2002-02-13 | 2002-04-03 | Pharmagene Lab Ltd | 5-HT 2B receptor antagonists |
GB0205690D0 (en) | 2002-03-09 | 2002-04-24 | Astrazeneca Ab | Chemical compounds |
GB0205688D0 (en) | 2002-03-09 | 2002-04-24 | Astrazeneca Ab | Chemical compounds |
GB0205693D0 (en) | 2002-03-09 | 2002-04-24 | Astrazeneca Ab | Chemical compounds |
JP2005524672A (ja) | 2002-03-09 | 2005-08-18 | アストラゼネカ アクチボラグ | Cdk阻害活性を有するイミダゾリル置換ピリミジン誘導体 |
US6872724B2 (en) | 2002-07-24 | 2005-03-29 | Merck & Co., Inc. | Polymorphs with tyrosine kinase activity |
US20040023978A1 (en) * | 2002-07-24 | 2004-02-05 | Yu Ren | Active salt forms with tyrosine kinase activity |
US20040023981A1 (en) * | 2002-07-24 | 2004-02-05 | Yu Ren | Salt forms with tyrosine kinase activity |
SG176311A1 (en) * | 2002-07-29 | 2011-12-29 | Rigel Pharmaceuticals | Methods of treating or preventing autoimmune diseases with 2,4-pyrimidinediamine compounds |
UA80767C2 (en) * | 2002-12-20 | 2007-10-25 | Pfizer Prod Inc | Pyrimidine derivatives for the treatment of abnormal cell growth |
US7109337B2 (en) * | 2002-12-20 | 2006-09-19 | Pfizer Inc | Pyrimidine derivatives for the treatment of abnormal cell growth |
ES2338545T3 (es) * | 2002-12-20 | 2010-05-10 | Pfizer Products Inc. | Derivados de pirimidina para el tratamiento del crecimiento celular anormal. |
GB0311276D0 (en) | 2003-05-16 | 2003-06-18 | Astrazeneca Ab | Chemical compounds |
GB0311274D0 (en) | 2003-05-16 | 2003-06-18 | Astrazeneca Ab | Chemical compounds |
EP1648876A1 (en) * | 2003-07-24 | 2006-04-26 | Pharmagene Laboratories Ltd | 5-ht sb 2b /sb receptor antagonists |
JP2007500683A (ja) * | 2003-07-25 | 2007-01-18 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | 抗菌剤としての、置換された2,4−ビス(アルキルアミノ)ピリミジン又は−キナゾリンの使用 |
CN102358738A (zh) * | 2003-07-30 | 2012-02-22 | 里格尔药品股份有限公司 | 2,4-嘧啶二胺化合物及其预防和治疗自体免疫疾病的用途 |
US20070099938A1 (en) * | 2003-10-24 | 2007-05-03 | Ono Pharmaceutical Co., Ltd. | Antistress drug and medical use thereof |
JP2007519754A (ja) * | 2004-01-30 | 2007-07-19 | スミスクライン ビーチャム コーポレーション | 化合物 |
TW200528101A (en) | 2004-02-03 | 2005-09-01 | Astrazeneca Ab | Chemical compounds |
EP1716867A4 (en) | 2004-02-20 | 2009-09-23 | Astellas Pharma Inc | PRENENT AGENTS FOR MIGRAINE |
AU2005232745A1 (en) * | 2004-04-13 | 2005-10-27 | Astellas Pharma Inc. | Polycyclic pyrimidines as potassium ion channel modulators |
US20060205945A1 (en) * | 2004-05-14 | 2006-09-14 | Pfizer Inc | Pyrimidine derivatives for the treatment of abnormal cell growth |
EP1756090A1 (en) * | 2004-05-14 | 2007-02-28 | Pfizer Products Incorporated | Pyrimidine derivatives for the treatment of abnormal cell growth |
EP1758887A1 (en) * | 2004-05-14 | 2007-03-07 | Pfizer Products Incorporated | Pyrimidine derivatives for the treatment of abnormal cell growth |
WO2005111022A1 (en) * | 2004-05-14 | 2005-11-24 | Pfizer Products Inc. | Pyrimidines derivatives for the treatment of abnormal cell growth |
CA2581454A1 (en) * | 2004-09-23 | 2006-03-30 | Reddy Us Therapeutics, Inc. | Novel pyrimidine compounds, process for their preparation and compositions containing them |
WO2006068770A1 (en) * | 2004-11-24 | 2006-06-29 | Rigel Pharmaceuticals, Inc. | Spiro-2, 4-pyrimidinediamine compounds and their uses |
GB0500492D0 (en) * | 2005-01-11 | 2005-02-16 | Cyclacel Ltd | Compound |
CA2591948C (en) | 2005-01-19 | 2013-11-12 | Rigel Pharmaceuticals, Inc. | Prodrugs of 2,4-pyrimidinediamine compounds and their uses |
CN101151249B (zh) * | 2005-03-31 | 2011-04-06 | 辉瑞产品公司 | 环戊吡啶及四氢喹啉衍生物 |
US20060270694A1 (en) * | 2005-05-03 | 2006-11-30 | Rigel Pharmaceuticals, Inc. | JAK kinase inhibitors and their uses |
CA2612227C (en) | 2005-06-14 | 2014-04-22 | Taigen Biotechnology Co., Ltd. | Pyrimidine compounds |
US8193206B2 (en) | 2005-06-14 | 2012-06-05 | Taigen Biotechnology Co., Ltd. | Pyrimidine compounds |
AU2006296386A1 (en) | 2005-09-30 | 2007-04-05 | Astrazeneca Ab | Imidazo [1,2-a] pyridine having anti-cell-proliferation activity |
WO2007062417A1 (en) * | 2005-11-28 | 2007-05-31 | Kalypsys, Inc. | Methods of preparing 2-imidazol-1-yl-4-methyl-6-pyrrolidin-2-yl-pyrimidine and 4-(1-alkylpyrrolidin-2-yl)-2-(1h-imidazol-1-yl)-6-methylpyrimidine derivatives |
ATE542794T1 (de) | 2006-02-20 | 2012-02-15 | Astellas Pharma Inc | Pyrrolderivat oder salz davon |
AR061185A1 (es) | 2006-05-26 | 2008-08-13 | Chugai Pharmaceutical Co Ltd | Compuestos heterociclicos como inhibidores de hsp90. composiciones farmaceuticas. |
AU2007336918A1 (en) * | 2006-12-22 | 2008-07-03 | Novartis Ag | Indol-4-yl-pyrimidinyl-2-yl-amine derivatives and use thereof as cyclin dependant kinase inhibitors |
ATE553107T1 (de) | 2007-03-01 | 2012-04-15 | Chugai Pharmaceutical Co Ltd | Makrocyclische verbindung |
DK2146779T3 (en) | 2007-04-18 | 2016-11-28 | Pfizer Prod Inc | Sulfonylamid derivatives to treat abnormal cell growth. |
KR101294731B1 (ko) * | 2007-06-04 | 2013-08-16 | 삼성디스플레이 주식회사 | 어레이 기판, 이를 갖는 표시패널 및 이의 제조방법 |
PT2190825E (pt) * | 2007-08-22 | 2014-07-16 | Irm Llc | Compostos e composições de 5-(4- (haloalcoxi)fenil)pirimidina-2-amina como inibidores de cinases |
RU2378278C2 (ru) * | 2008-01-24 | 2010-01-10 | Андрей Александрович Иващенко | ЗАМЕЩЕННЫЕ 3-СУЛЬФОНИЛ-[1,2,3]ТРИАЗОЛО[1,5-a]ПИРИМИДИНЫ-АНТАГОНИСТЫ СЕРОТОНИНОВЫХ 5-HT6 РЕЦЕПТОРОВ, СПОСОБЫ ИХ ПОЛУЧЕНИЯ И ПРИМЕНЕНИЕ |
NZ594937A (en) | 2008-02-19 | 2013-03-28 | Adolor Corp | Beloxepin, its enantiomers, and analogs thereof for the treatment of pain |
AU2008355098B2 (en) | 2008-04-21 | 2012-11-15 | Gpcr Therapeutics, Inc | Heterocyclic compounds |
EP2432767B1 (en) * | 2009-05-19 | 2013-06-26 | Dow AgroSciences LLC | Compounds and methods for controlling fungi |
NZ601508A (en) | 2009-12-30 | 2013-07-26 | Arqule Inc | Substituted naphthalenyl-pyrimidine compounds and the use thereof in the treatment of cancer |
CN102786512A (zh) * | 2012-05-31 | 2012-11-21 | 中国人民解放军军事医学科学院毒物药物研究所 | N-芳基不饱和稠环叔胺类化合物及其制备方法和抗肿瘤应用 |
EP3154547B1 (en) | 2014-06-13 | 2023-06-07 | Yuma Therapeutics, Inc. | Pyrimidine compounds and methods using the same |
CN104725322B (zh) * | 2015-02-16 | 2017-05-24 | 同济大学 | 一种2‑胺基嘧啶类化合物及其制备方法 |
CN107614503B (zh) * | 2015-04-29 | 2020-03-10 | 广东众生药业股份有限公司 | 稠环或三环芳基嘧啶化合物用作激酶抑制剂 |
RU2605265C1 (ru) * | 2015-10-06 | 2016-12-20 | федеральное государственное бюджетное образовательное учреждение высшего образования "Санкт-Петербургская государственная химико-фармацевтическая академия" Министерства здравоохранения Российской Федерации (ФГБОУ ВО СПХФА Минздрава России) | Анальгезирующее и противовоспалительное средство на основе 5-бутил-6-гидрокси-2-метилпиримидин-4(3h)-она |
CN109311858B (zh) | 2016-05-26 | 2021-12-03 | 里科瑞尔姆Ip控股有限责任公司 | Egfr抑制剂化合物 |
AU2018352695A1 (en) | 2017-10-19 | 2020-05-28 | Effector Therapeutics, Inc. | Benzimidazole-indole inhibitors of Mnk1 and Mnk2 |
CN108904503B (zh) * | 2018-07-02 | 2021-09-28 | 陕西科技大学 | 6-氯-5-硝基-2,4-二氨基嘧啶在治疗慢性粒细胞白血病药物中的应用 |
TWI782504B (zh) | 2020-05-08 | 2022-11-01 | 美商美國禮來大藥廠 | (三氟甲基)嘧啶-2-胺化合物 |
CN114907273A (zh) * | 2022-06-09 | 2022-08-16 | 乐威医药(江苏)股份有限公司 | 2-氨基嘧啶-6-芳基化合物的制备方法 |
Family Cites Families (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3535330A (en) * | 1968-04-29 | 1970-10-20 | Sandoz Ag | 2,6-diphenyl - 4 - (p-(dilower-alkyl amino lower - alkoxy)phenyl)pyridines and derivatives thereof |
US3965101A (en) * | 1973-07-26 | 1976-06-22 | E. R. Squibb & Sons, Inc. | 1-(O-Bromo-phenoxyalkyl)-1,2-dihydro-2-iminopyrimidines |
DE2750288A1 (de) * | 1977-11-10 | 1979-05-17 | Thomae Gmbh Dr K | Neue 9-(omega-heteroarylamino- alkylamino)-erythromycine, ihre salze, verfahren zu ihrer herstellung und diese enthaltende arzneimittel |
US4543248A (en) * | 1979-03-19 | 1985-09-24 | The Upjohn Company | Method for immunoregulation with 6-aryl pyrimidine compounds |
US4665077A (en) * | 1979-03-19 | 1987-05-12 | The Upjohn Company | Method for treating rejection of organ or skin grafts with 6-aryl pyrimidine compounds |
US5002951A (en) * | 1979-03-19 | 1991-03-26 | The Upjohn Company | Method for treating bacterial and protozoal infections |
AU531507B2 (en) * | 1979-08-08 | 1983-08-25 | G.D. Searle & Co. | 8-substituted 7-phenyl-1,2,4-triazolo(4,3-c) pyrimidines -5-amines and amides |
US4619933A (en) * | 1979-09-28 | 1986-10-28 | The Upjohn Company | 6-aryl pyrimidines for treating aplastic anemia |
FR2539741A1 (fr) * | 1983-01-21 | 1984-07-27 | Sanofi Sa | Composes a noyau heterocyclique diazote, leur procede de preparation et les medicaments, actifs sur le systeme nerveux central, qui en contiennent |
US4512993A (en) * | 1983-07-25 | 1985-04-23 | Sterling Drug Inc. | 4(Or 5)-(pyridinyl)-2-pyrimidinamines and cardiotonic use thereof |
US4504482A (en) * | 1983-07-28 | 1985-03-12 | Sterling Drug Inc. | [5(or 4)-(Pyridinyl)-2-pyrimidinyl]ureas and cardiotonic use thereof |
JPS62501632A (ja) * | 1985-02-05 | 1987-07-02 | ジ・アップジョン・カンパニ− | 4−置換−6−アリ−ルピリミジン化合物 |
US4711888A (en) * | 1985-07-24 | 1987-12-08 | Pfizer Inc. | Hydroxy and alkoxy pyrimidines |
US4929726A (en) * | 1988-02-09 | 1990-05-29 | Georgia State University Foundation, Inc. | Novel diazines and their method of preparation |
AU3752589A (en) * | 1988-05-16 | 1989-12-12 | Georgia State University Research Foundation, Inc. | Nucleic acid interacting unfused heteropolycyclic compounds |
HU206337B (en) * | 1988-12-29 | 1992-10-28 | Mitsui Petrochemical Ind | Process for producing pyrimidine derivatives and pharmaceutical compositions |
IE63502B1 (en) * | 1989-04-21 | 1995-05-03 | Zeneca Ltd | Aminopyrimidine derivatives useful for treating cardiovascular disorders |
GB9012311D0 (en) * | 1990-06-01 | 1990-07-18 | Wellcome Found | Pharmacologically active cns compounds |
JP2648897B2 (ja) * | 1991-07-01 | 1997-09-03 | 塩野義製薬株式会社 | ピリミジン誘導体 |
DE4237768A1 (en) * | 1991-11-12 | 1993-05-13 | Ciba Geigy Ag | New polyarylene ether derivs. with reduced viscosity - used to prepare moulded bodies, foils, fibres and membranes, as matrix resins, adhesives or coating agents or as polymer additives |
US5698444A (en) * | 1993-12-23 | 1997-12-16 | Eli Lilly And Company | Serotonin receptor protein and related nucleic acid compounds |
US5688807A (en) * | 1994-03-11 | 1997-11-18 | Eli Lilly And Company | Method for treating 5HT2B receptor related conditions |
US5786355A (en) * | 1995-04-13 | 1998-07-28 | Taiho Pharmaceutical Co., Ltd. | 4,6-diarylpyrimidine derivatives and salts thereof |
US5795905A (en) * | 1995-06-06 | 1998-08-18 | Neurocrine Biosciences, Inc. | CRF receptor antagonists and methods relating thereto |
-
1997
- 1997-05-09 TW TW086106209A patent/TW440563B/zh not_active IP Right Cessation
- 1997-05-14 IL IL12705697A patent/IL127056A/xx not_active IP Right Cessation
- 1997-05-14 NZ NZ332802A patent/NZ332802A/xx unknown
- 1997-05-14 CZ CZ19983803A patent/CZ291849B6/cs not_active IP Right Cessation
- 1997-05-14 WO PCT/EP1997/002454 patent/WO1997044326A1/en active IP Right Grant
- 1997-05-14 EP EP97923071A patent/EP0901474B1/en not_active Expired - Lifetime
- 1997-05-14 TR TR1998/02391T patent/TR199802391T2/xx unknown
- 1997-05-14 AU AU28978/97A patent/AU725891B2/en not_active Ceased
- 1997-05-14 BR BR9709599A patent/BR9709599A/pt not_active Application Discontinuation
- 1997-05-14 RU RU98123001/04A patent/RU2189976C2/ru not_active IP Right Cessation
- 1997-05-14 HU HU9901535A patent/HUP9901535A3/hu unknown
- 1997-05-14 PT PT97923071T patent/PT901474E/pt unknown
- 1997-05-14 KR KR10-1998-0709451A patent/KR100518101B1/ko not_active IP Right Cessation
- 1997-05-14 ES ES97923071T patent/ES2262178T3/es not_active Expired - Lifetime
- 1997-05-14 JP JP54148297A patent/JP2001525794A/ja not_active Ceased
- 1997-05-14 CN CN97196018A patent/CN1109675C/zh not_active Expired - Fee Related
- 1997-05-14 AT AT97923071T patent/ATE323682T1/de not_active IP Right Cessation
- 1997-05-14 DE DE69735712T patent/DE69735712T2/de not_active Expired - Fee Related
- 1997-05-14 DK DK97923071T patent/DK0901474T3/da active
- 1997-05-14 CA CA002255705A patent/CA2255705A1/en not_active Abandoned
- 1997-05-20 MY MYPI97002204A patent/MY119181A/en unknown
- 1997-05-20 HR HR970275A patent/HRP970275B1/xx not_active IP Right Cessation
- 1997-05-20 US US08/858,964 patent/US5863924A/en not_active Expired - Fee Related
- 1997-05-21 MA MA24630A patent/MA26431A1/fr unknown
- 1997-05-22 AR ARP970102176A patent/AR007253A1/es unknown
- 1997-05-22 UY UY24560A patent/UY24560A1/es not_active IP Right Cessation
- 1997-05-22 CO CO97028097A patent/CO4950514A1/es unknown
- 1997-05-23 ID IDP971727A patent/ID16969A/id unknown
- 1997-07-01 SA SA97180191A patent/SA97180191B1/ar unknown
- 1997-07-01 SA SA05260356A patent/SA05260356B1/ar unknown
-
1998
- 1998-11-19 NO NO19985392A patent/NO311800B1/no not_active Application Discontinuation
- 1998-11-23 YU YU53298A patent/YU53298A/sr unknown
-
1999
- 1999-11-29 HK HK99105532A patent/HK1020345A1/xx not_active IP Right Cessation
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
NO311800B1 (no) | Arylpyrimidinderivater | |
US5958934A (en) | Aryl pyrimidine derivatives and uses thereof | |
US5952331A (en) | Aryl pyrimidine derivatives | |
US20220048858A1 (en) | Aza (Indole)-, Benzothiophene-, And Benzofuran-3-Sulfonamides | |
KR100258052B1 (ko) | 5ht2c-수용체 길항제로서의 피리미딘 유도체 및 이를 포함하는 약물 | |
JP2019194235A (ja) | ヘテロアリール化合物およびそれらの使用 | |
US6313126B1 (en) | Arylpiperazinyl-cyclohexyl indole derivatives for the treatment of depression | |
JP2013515786A (ja) | ヘテロアリール化合物およびそれらの使用 | |
MX2011002399A (es) | Compuestos pirimidina tri-sustituida y su uso como inhibidores de fosfodiesterasa 10. | |
EP2953943A1 (en) | Substituted bicyclic dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity | |
EP1321169A1 (en) | Combination of a serotonin receptor antagonist with a histidine decarboxylase inhibitor as a medicament | |
PL190547B1 (pl) | Pochodne arylo-pirymidyny, zawierające je kompozycje farmaceutyczne, sposoby ich wytwarzania, oraz ich zastosowanie do wytwarzania środków leczniczych | |
US7348332B2 (en) | (3,4-dihydro-quinazolin-2-yl)-indan-1-yl-amines | |
SA05260355B1 (ar) | مشتقات اريل بيريميدين aryl pyrimidine واستخداماتها | |
US6150533A (en) | N-aryloxyethyl-indoly-alkylamines for the treatment of depression |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
FC2A | Withdrawal, rejection or dismissal of laid open patent application |