NO811568L - Substituerte fenyletere. - Google Patents
Substituerte fenyletere.Info
- Publication number
- NO811568L NO811568L NO811568A NO811568A NO811568L NO 811568 L NO811568 L NO 811568L NO 811568 A NO811568 A NO 811568A NO 811568 A NO811568 A NO 811568A NO 811568 L NO811568 L NO 811568L
- Authority
- NO
- Norway
- Prior art keywords
- phenoxy
- residue
- hydroxy
- formula
- trifluoromethyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 109
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 56
- 239000001257 hydrogen Substances 0.000 claims abstract description 50
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 50
- 150000003839 salts Chemical class 0.000 claims abstract description 46
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 34
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 122
- 239000000203 mixture Substances 0.000 claims description 62
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 39
- 238000006243 chemical reaction Methods 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 33
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
- 125000006239 protecting group Chemical group 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 23
- 150000002367 halogens Chemical class 0.000 claims description 20
- 229910021529 ammonia Inorganic materials 0.000 claims description 19
- 125000000524 functional group Chemical group 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- 125000002883 imidazolyl group Chemical group 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000001589 carboacyl group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 125000003700 epoxy group Chemical group 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 230000002829 reductive effect Effects 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 125000001425 triazolyl group Chemical group 0.000 claims description 4
- 230000007306 turnover Effects 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000005479 oxodihydropyridyl group Chemical group 0.000 claims 1
- -1 phenylene radical Chemical group 0.000 abstract description 79
- 239000002253 acid Substances 0.000 abstract description 24
- 125000002947 alkylene group Chemical group 0.000 abstract description 8
- 239000013543 active substance Substances 0.000 abstract description 7
- 229910052799 carbon Inorganic materials 0.000 abstract description 6
- 239000003638 chemical reducing agent Substances 0.000 abstract description 5
- 230000000903 blocking effect Effects 0.000 abstract description 4
- 231100000252 nontoxic Toxicity 0.000 abstract description 4
- 230000003000 nontoxic effect Effects 0.000 abstract description 4
- 206010002383 Angina Pectoris Diseases 0.000 abstract description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 2
- 208000035475 disorder Diseases 0.000 abstract description 2
- 206010020871 hypertrophic cardiomyopathy Diseases 0.000 abstract description 2
- 230000033764 rhythmic process Effects 0.000 abstract description 2
- 102000012740 beta Adrenergic Receptors Human genes 0.000 abstract 1
- 108010079452 beta Adrenergic Receptors Proteins 0.000 abstract 1
- 239000002876 beta blocker Substances 0.000 abstract 1
- 239000000496 cardiotonic agent Substances 0.000 abstract 1
- 230000003177 cardiotonic effect Effects 0.000 abstract 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 abstract 1
- 210000004165 myocardium Anatomy 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 231
- 239000000243 solution Substances 0.000 description 159
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 99
- 229960004592 isopropanol Drugs 0.000 description 74
- 238000002844 melting Methods 0.000 description 73
- 230000008018 melting Effects 0.000 description 73
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 68
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 66
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 58
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 52
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 47
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 47
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 45
- 239000003054 catalyst Substances 0.000 description 45
- 239000007858 starting material Substances 0.000 description 45
- 239000002904 solvent Substances 0.000 description 44
- 239000003921 oil Substances 0.000 description 40
- 239000011541 reaction mixture Substances 0.000 description 40
- 239000000706 filtrate Substances 0.000 description 38
- 238000010992 reflux Methods 0.000 description 37
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 35
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 29
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
- 239000012074 organic phase Substances 0.000 description 28
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 27
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 26
- 238000001704 evaporation Methods 0.000 description 26
- 239000000741 silica gel Substances 0.000 description 26
- 229910002027 silica gel Inorganic materials 0.000 description 26
- 238000003756 stirring Methods 0.000 description 25
- 229910000027 potassium carbonate Inorganic materials 0.000 description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 23
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 23
- 235000011181 potassium carbonates Nutrition 0.000 description 23
- 238000001816 cooling Methods 0.000 description 20
- 230000008020 evaporation Effects 0.000 description 20
- 239000000725 suspension Substances 0.000 description 20
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 19
- 238000001953 recrystallisation Methods 0.000 description 18
- 239000013078 crystal Substances 0.000 description 16
- 238000001035 drying Methods 0.000 description 16
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 15
- FOQTVXMTYFCHSL-UHFFFAOYSA-N 5-[2-(benzylamino)ethoxy]-2-hydroxybenzamide Chemical compound C1=C(O)C(C(=O)N)=CC(OCCNCC=2C=CC=CC=2)=C1 FOQTVXMTYFCHSL-UHFFFAOYSA-N 0.000 description 15
- 238000001914 filtration Methods 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 13
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 13
- 229940098779 methanesulfonic acid Drugs 0.000 description 13
- 229910052938 sodium sulfate Inorganic materials 0.000 description 13
- 235000011152 sodium sulphate Nutrition 0.000 description 13
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 12
- 150000002431 hydrogen Chemical class 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 239000002244 precipitate Substances 0.000 description 10
- 238000010626 work up procedure Methods 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 9
- 235000011121 sodium hydroxide Nutrition 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 8
- 125000001118 alkylidene group Chemical group 0.000 description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 238000002425 crystallisation Methods 0.000 description 8
- 230000008025 crystallization Effects 0.000 description 8
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 8
- GKJZEKSHCJELPL-UHFFFAOYSA-N 2-hydroxy-5-[2-[[2-hydroxy-3-[4-[1-methyl-4-(trifluoromethyl)-2-imidazolyl]phenoxy]propyl]amino]ethoxy]benzamide Chemical compound CN1C=C(C(F)(F)F)N=C1C(C=C1)=CC=C1OCC(O)CNCCOC1=CC=C(O)C(C(N)=O)=C1 GKJZEKSHCJELPL-UHFFFAOYSA-N 0.000 description 7
- 125000002252 acyl group Chemical group 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- QDIZHHHKKKRTAB-UHFFFAOYSA-N 1-methyl-2-[4-(oxiran-2-ylmethoxy)phenyl]-4-(trifluoromethyl)imidazole Chemical compound CN1C=C(C(F)(F)F)N=C1C(C=C1)=CC=C1OCC1OC1 QDIZHHHKKKRTAB-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 150000001735 carboxylic acids Chemical class 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 239000006260 foam Substances 0.000 description 6
- 238000005984 hydrogenation reaction Methods 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 239000000155 melt Substances 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- FFEARJCKVFRZRR-UHFFFAOYSA-N methionine Chemical compound CSCCC(N)C(O)=O FFEARJCKVFRZRR-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 150000002989 phenols Chemical class 0.000 description 6
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 6
- JISUOXAQSZWMCR-UHFFFAOYSA-N 1-amino-3-[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenoxy]propan-2-ol Chemical compound CN1C=C(C(F)(F)F)N=C1C1=CC=C(OCC(O)CN)C=C1 JISUOXAQSZWMCR-UHFFFAOYSA-N 0.000 description 5
- 241000282326 Felis catus Species 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 150000001728 carbonyl compounds Chemical class 0.000 description 5
- 230000000747 cardiac effect Effects 0.000 description 5
- 239000012230 colorless oil Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 125000001072 heteroaryl group Chemical group 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 235000015497 potassium bicarbonate Nutrition 0.000 description 5
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 5
- 239000011736 potassium bicarbonate Substances 0.000 description 5
- 229960000581 salicylamide Drugs 0.000 description 5
- 239000011877 solvent mixture Substances 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 4
- HEPPAPZASXFWTB-UHFFFAOYSA-N 3,3-dibromo-1,1,1-trifluoropropan-2-one Chemical compound FC(F)(F)C(=O)C(Br)Br HEPPAPZASXFWTB-UHFFFAOYSA-N 0.000 description 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 4
- YWICNZAFLMJZHZ-UHFFFAOYSA-N 4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenol Chemical compound CN1C=C(C(F)(F)F)N=C1C1=CC=C(O)C=C1 YWICNZAFLMJZHZ-UHFFFAOYSA-N 0.000 description 4
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 4
- GPWXTFYFEXNIBL-UHFFFAOYSA-N 5-(2-aminoethoxy)-2-hydroxybenzamide Chemical compound NCCOC1=CC=C(O)C(C(N)=O)=C1 GPWXTFYFEXNIBL-UHFFFAOYSA-N 0.000 description 4
- 241000700199 Cavia porcellus Species 0.000 description 4
- 201000004624 Dermatitis Diseases 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 235000011054 acetic acid Nutrition 0.000 description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 208000010668 atopic eczema Diseases 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- 238000001990 intravenous administration Methods 0.000 description 4
- 235000010755 mineral Nutrition 0.000 description 4
- 239000011707 mineral Substances 0.000 description 4
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000001632 sodium acetate Substances 0.000 description 4
- 235000017281 sodium acetate Nutrition 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- NUGDSIUOFOWNOM-UHFFFAOYSA-N 1-methyl-3-methylsulfanyl-5-[4-(oxiran-2-ylmethoxy)phenyl]-1,2,4-triazole Chemical compound CN1N=C(SC)N=C1C(C=C1)=CC=C1OCC1OC1 NUGDSIUOFOWNOM-UHFFFAOYSA-N 0.000 description 3
- LDTQLZLSEZDKSZ-UHFFFAOYSA-N 2-(4-methoxyphenyl)-1-methyl-4-(trifluoromethyl)imidazole Chemical compound C1=CC(OC)=CC=C1C1=NC(C(F)(F)F)=CN1C LDTQLZLSEZDKSZ-UHFFFAOYSA-N 0.000 description 3
- XWALBVFWCNKGRZ-UHFFFAOYSA-N 2-(4-methoxyphenyl)-5-(trifluoromethyl)-1h-imidazole Chemical compound C1=CC(OC)=CC=C1C1=NC=C(C(F)(F)F)N1 XWALBVFWCNKGRZ-UHFFFAOYSA-N 0.000 description 3
- CFFHQPFVUKPUDA-UHFFFAOYSA-N 2-methyl-5-[4-(oxiran-2-ylmethoxy)phenyl]tetrazole Chemical compound CN1N=NC(C=2C=CC(OCC3OC3)=CC=2)=N1 CFFHQPFVUKPUDA-UHFFFAOYSA-N 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- XHSXHCARWOCRED-UHFFFAOYSA-N 4-[1-methyl-5-(trifluoromethyl)imidazol-2-yl]phenol Chemical compound C1=C(C(F)(F)F)N(C)C(C=2C=CC(O)=CC=2)=N1 XHSXHCARWOCRED-UHFFFAOYSA-N 0.000 description 3
- WCHIQNINONSNKW-UHFFFAOYSA-N 4-[2-(benzylamino)ethoxy]-2-hydroxybenzamide Chemical compound C1=C(O)C(C(=O)N)=CC=C1OCCNCC1=CC=CC=C1 WCHIQNINONSNKW-UHFFFAOYSA-N 0.000 description 3
- KCIMYLNJQIVHEU-UHFFFAOYSA-N 5-[2-[benzyl-[2-hydroxy-3-[4-(1,3-thiazol-2-yl)phenoxy]propyl]amino]ethoxy]-2-hydroxybenzamide Chemical compound C1=C(O)C(C(=O)N)=CC(OCCN(CC(O)COC=2C=CC(=CC=2)C=2SC=CN=2)CC=2C=CC=CC=2)=C1 KCIMYLNJQIVHEU-UHFFFAOYSA-N 0.000 description 3
- WWERXXGTALGONZ-UHFFFAOYSA-N 5-[2-[benzyl-[2-hydroxy-3-[4-[1-methyl-5-(trifluoromethyl)imidazol-2-yl]phenoxy]propyl]amino]ethoxy]-2-hydroxybenzamide Chemical compound CN1C(C(F)(F)F)=CN=C1C(C=C1)=CC=C1OCC(O)CN(CC=1C=CC=CC=1)CCOC1=CC=C(O)C(C(N)=O)=C1 WWERXXGTALGONZ-UHFFFAOYSA-N 0.000 description 3
- WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 239000011975 tartaric acid Substances 0.000 description 3
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
- QTFDGQBSIBRCDG-UHFFFAOYSA-N 1,2-dimethyl-5-[3-(oxiran-2-ylmethoxy)phenyl]pyrrole Chemical compound CN1C(C)=CC=C1C1=CC=CC(OCC2OC2)=C1 QTFDGQBSIBRCDG-UHFFFAOYSA-N 0.000 description 2
- LVKDMUXEESFMDS-UHFFFAOYSA-N 1-[1,5-dimethyl-2-[4-(oxiran-2-ylmethoxy)phenyl]imidazol-4-yl]ethanone Chemical compound CN1C(C)=C(C(=O)C)N=C1C(C=C1)=CC=C1OCC1OC1 LVKDMUXEESFMDS-UHFFFAOYSA-N 0.000 description 2
- DPBKLWYQNXFLLN-UHFFFAOYSA-N 1-benzyl-2-[5-(4-methoxyphenyl)furan-2-yl]-4-(trifluoromethyl)imidazole Chemical compound C1=CC(OC)=CC=C1C1=CC=C(C=2N(C=C(N=2)C(F)(F)F)CC=2C=CC=CC=2)O1 DPBKLWYQNXFLLN-UHFFFAOYSA-N 0.000 description 2
- CISNRVOVXPVXOV-UHFFFAOYSA-N 1-methyl-2-[4-(oxiran-2-ylmethoxy)phenyl]-5-(trifluoromethyl)imidazole Chemical compound CN1C(C(F)(F)F)=CN=C1C(C=C1)=CC=C1OCC1OC1 CISNRVOVXPVXOV-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- IUNJCFABHJZSKB-UHFFFAOYSA-N 2,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C(O)=C1 IUNJCFABHJZSKB-UHFFFAOYSA-N 0.000 description 2
- QJQIUJIUYMABJY-UHFFFAOYSA-N 2-(4-methoxyphenyl)-1-propan-2-yl-4-(trifluoromethyl)imidazole Chemical compound C1=CC(OC)=CC=C1C1=NC(C(F)(F)F)=CN1C(C)C QJQIUJIUYMABJY-UHFFFAOYSA-N 0.000 description 2
- PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 description 2
- GXANCFOKAWEPIS-UHFFFAOYSA-N 2-[(4-phenylphenoxy)methyl]oxirane Chemical group C1OC1COC(C=C1)=CC=C1C1=CC=CC=C1 GXANCFOKAWEPIS-UHFFFAOYSA-N 0.000 description 2
- OTOAQBYIEPXSNA-UHFFFAOYSA-N 2-[2-(4-methoxyphenyl)-4-(trifluoromethyl)imidazol-1-yl]ethanol Chemical compound C1=CC(OC)=CC=C1C1=NC(C(F)(F)F)=CN1CCO OTOAQBYIEPXSNA-UHFFFAOYSA-N 0.000 description 2
- JCBBXBKWFNQXFE-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)phenyl]-1,3-thiazole Chemical compound C1OC1COC(C=C1)=CC=C1C1=NC=CS1 JCBBXBKWFNQXFE-UHFFFAOYSA-N 0.000 description 2
- DPHPZBFGSBMAKL-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)phenyl]-4-(trifluoromethyl)-1,3-thiazole Chemical compound FC(F)(F)C1=CSC(C=2C=CC(OCC3OC3)=CC=2)=N1 DPHPZBFGSBMAKL-UHFFFAOYSA-N 0.000 description 2
- LQHLCFKMIARYCI-UHFFFAOYSA-N 2-hydroxy-5-[2-[[2-hydroxy-3-[4-[5-(trifluoromethyl)-1h-imidazol-2-yl]phenoxy]propyl]amino]ethoxy]benzamide Chemical compound C1=C(O)C(C(=O)N)=CC(OCCNCC(O)COC=2C=CC(=CC=2)C=2NC=C(N=2)C(F)(F)F)=C1 LQHLCFKMIARYCI-UHFFFAOYSA-N 0.000 description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- ICLBVHXROGDRRM-UHFFFAOYSA-N 3-(1,5-dimethylpyrrol-2-yl)phenol Chemical compound CN1C(C)=CC=C1C1=CC=CC(O)=C1 ICLBVHXROGDRRM-UHFFFAOYSA-N 0.000 description 2
- LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
- XGYPEXYYRLMDAO-UHFFFAOYSA-N 4,6-dimethyl-2-[4-(oxiran-2-ylmethoxy)phenyl]pyrimidine Chemical compound CC1=CC(C)=NC(C=2C=CC(OCC3OC3)=CC=2)=N1 XGYPEXYYRLMDAO-UHFFFAOYSA-N 0.000 description 2
- QXJQTKRIVOVDQV-UHFFFAOYSA-N 4-[1-(2-hydroxyethyl)-4-(trifluoromethyl)imidazol-2-yl]phenol Chemical compound OCCN1C=C(C(F)(F)F)N=C1C1=CC=C(O)C=C1 QXJQTKRIVOVDQV-UHFFFAOYSA-N 0.000 description 2
- SCYNEQPXCUBKQV-UHFFFAOYSA-N 4-[2-[benzyl-[2-hydroxy-3-[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenoxy]propyl]amino]ethoxy]-2-hydroxybenzamide Chemical compound CN1C=C(C(F)(F)F)N=C1C(C=C1)=CC=C1OCC(O)CN(CC=1C=CC=CC=1)CCOC1=CC=C(C(N)=O)C(O)=C1 SCYNEQPXCUBKQV-UHFFFAOYSA-N 0.000 description 2
- MHEVFQYLMPAKAE-UHFFFAOYSA-N 4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]phenol Chemical compound C1=CC(O)=CC=C1C1=NC(C(F)(F)F)=CS1 MHEVFQYLMPAKAE-UHFFFAOYSA-N 0.000 description 2
- RILAZBDWTVQANQ-UHFFFAOYSA-N 4-[5-[1-benzyl-4-(trifluoromethyl)imidazol-2-yl]furan-2-yl]phenol Chemical compound C1=CC(O)=CC=C1C1=CC=C(C=2N(C=C(N=2)C(F)(F)F)CC=2C=CC=CC=2)O1 RILAZBDWTVQANQ-UHFFFAOYSA-N 0.000 description 2
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
- CDRMHPSUMLXGRA-UHFFFAOYSA-N 4-methyl-2-[4-(oxiran-2-ylmethoxy)phenyl]-6-(trifluoromethyl)pyrimidine Chemical compound CC1=CC(C(F)(F)F)=NC(C=2C=CC(OCC3OC3)=CC=2)=N1 CDRMHPSUMLXGRA-UHFFFAOYSA-N 0.000 description 2
- XGMHJLNAFGPIDY-UHFFFAOYSA-N 4-methyl-3-methylsulfanyl-5-[4-(oxiran-2-ylmethoxy)phenyl]-1,2,4-triazole Chemical compound CN1C(SC)=NN=C1C(C=C1)=CC=C1OCC1OC1 XGMHJLNAFGPIDY-UHFFFAOYSA-N 0.000 description 2
- JPCUGGGXLKGQEP-UHFFFAOYSA-N 5-(4-methoxyphenyl)furan-2-carbaldehyde Chemical compound C1=CC(OC)=CC=C1C1=CC=C(C=O)O1 JPCUGGGXLKGQEP-UHFFFAOYSA-N 0.000 description 2
- KXBVFGXQMXTQEF-UHFFFAOYSA-N 5-[1-(benzylamino)-5-[4-(1,4-dimethyl-6-oxopyrimidin-2-yl)oxyphenoxy]-4-hydroxypentoxy]-2-hydroxybenzamide Chemical compound CC1=CC(=O)N(C)C(OC=2C=CC(OCC(O)CCC(NCC=3C=CC=CC=3)OC=3C=C(C(O)=CC=3)C(N)=O)=CC=2)=N1 KXBVFGXQMXTQEF-UHFFFAOYSA-N 0.000 description 2
- PPQSGAHQQQVIEN-UHFFFAOYSA-N 5-[2-[[3-[4-(4-acetyl-1,5-dimethylimidazol-2-yl)phenoxy]-2-hydroxypropyl]-benzylamino]ethoxy]-2-hydroxybenzamide Chemical compound CN1C(C)=C(C(=O)C)N=C1C(C=C1)=CC=C1OCC(O)CN(CC=1C=CC=CC=1)CCOC1=CC=C(O)C(C(N)=O)=C1 PPQSGAHQQQVIEN-UHFFFAOYSA-N 0.000 description 2
- SZRAYQIJISWADT-UHFFFAOYSA-N 5-[2-[benzyl-[2-hydroxy-3-(4-phenylphenoxy)propyl]amino]ethoxy]-2-hydroxybenzamide Chemical compound C1=C(O)C(C(=O)N)=CC(OCCN(CC(O)COC=2C=CC(=CC=2)C=2C=CC=CC=2)CC=2C=CC=CC=2)=C1 SZRAYQIJISWADT-UHFFFAOYSA-N 0.000 description 2
- RFISCQAOBXIHPU-UHFFFAOYSA-N 5-[2-[benzyl-[2-hydroxy-3-[2-(1h-indol-2-yl)phenoxy]propyl]amino]ethoxy]-2-hydroxybenzamide Chemical compound C1=C(O)C(C(=O)N)=CC(OCCN(CC(O)COC=2C(=CC=CC=2)C=2NC3=CC=CC=C3C=2)CC=2C=CC=CC=2)=C1 RFISCQAOBXIHPU-UHFFFAOYSA-N 0.000 description 2
- PSJLVVTYWPMJKY-UHFFFAOYSA-N 5-[2-[benzyl-[2-hydroxy-3-[4-(1-methylimidazol-2-yl)phenoxy]propyl]amino]ethoxy]-2-phenylmethoxybenzamide Chemical compound CN1C=CN=C1C(C=C1)=CC=C1OCC(O)CN(CC=1C=CC=CC=1)CCOC(C=C1C(N)=O)=CC=C1OCC1=CC=CC=C1 PSJLVVTYWPMJKY-UHFFFAOYSA-N 0.000 description 2
- KLPLEHDIMCONMX-UHFFFAOYSA-N 5-[2-[benzyl-[2-hydroxy-3-[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenoxy]propyl]amino]ethoxy]-2-hydroxybenzamide Chemical compound CN1C=C(C(F)(F)F)N=C1C(C=C1)=CC=C1OCC(O)CN(CC=1C=CC=CC=1)CCOC1=CC=C(O)C(C(N)=O)=C1 KLPLEHDIMCONMX-UHFFFAOYSA-N 0.000 description 2
- CMURTTWWFNOPNR-UHFFFAOYSA-N 5-[2-[benzyl-[2-hydroxy-3-[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenoxy]propyl]amino]ethoxy]-2-phenylmethoxybenzamide Chemical compound CN1C=C(C(F)(F)F)N=C1C(C=C1)=CC=C1OCC(O)CN(CC=1C=CC=CC=1)CCOC(C=C1C(N)=O)=CC=C1OCC1=CC=CC=C1 CMURTTWWFNOPNR-UHFFFAOYSA-N 0.000 description 2
- UEXKBSPCBXXCML-UHFFFAOYSA-N 5-[2-[benzyl-[2-hydroxy-3-[4-[1-methyl-5-(trifluoromethyl)-1,2,4-triazol-3-yl]phenoxy]propyl]amino]ethoxy]-2-hydroxybenzamide Chemical compound N1=C(C(F)(F)F)N(C)N=C1C(C=C1)=CC=C1OCC(O)CN(CC=1C=CC=CC=1)CCOC1=CC=C(O)C(C(N)=O)=C1 UEXKBSPCBXXCML-UHFFFAOYSA-N 0.000 description 2
- VERALIUNTPBEMR-UHFFFAOYSA-N 5-[2-[benzyl-[2-hydroxy-3-[4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]phenoxy]propyl]amino]ethoxy]-2-hydroxybenzamide Chemical compound C1=C(O)C(C(=O)N)=CC(OCCN(CC(O)COC=2C=CC(=CC=2)C=2SC=C(N=2)C(F)(F)F)CC=2C=CC=CC=2)=C1 VERALIUNTPBEMR-UHFFFAOYSA-N 0.000 description 2
- YSKLUXFXSINTFR-UHFFFAOYSA-N 5-[2-[benzyl-[2-hydroxy-3-[4-[4-methyl-5-(trifluoromethyl)-1,2,4-triazol-3-yl]phenoxy]propyl]amino]ethoxy]-2-hydroxybenzamide Chemical compound N1=C(C(F)(F)F)N(C)C(C=2C=CC(OCC(O)CN(CCOC=3C=C(C(O)=CC=3)C(N)=O)CC=3C=CC=CC=3)=CC=2)=N1 YSKLUXFXSINTFR-UHFFFAOYSA-N 0.000 description 2
- FFWPKXBKYAKWGA-UHFFFAOYSA-N 5-[2-[benzyl-[2-hydroxy-3-[4-[4-methyl-6-(trifluoromethyl)pyrimidin-2-yl]phenoxy]propyl]amino]ethoxy]-2-hydroxybenzamide;hydrochloride Chemical compound Cl.CC1=CC(C(F)(F)F)=NC(C=2C=CC(OCC(O)CN(CCOC=3C=C(C(O)=CC=3)C(N)=O)CC=3C=CC=CC=3)=CC=2)=N1 FFWPKXBKYAKWGA-UHFFFAOYSA-N 0.000 description 2
- STJRPFWQLMFZBE-UHFFFAOYSA-N 5-[2-[benzyl-[2-hydroxy-3-[4-[5-(trifluoromethyl)-1h-imidazol-2-yl]phenoxy]propyl]amino]ethoxy]-2-phenylmethoxybenzamide Chemical compound C=1C=C(OCC=2C=CC=CC=2)C(C(=O)N)=CC=1OCCN(CC=1C=CC=CC=1)CC(O)COC(C=C1)=CC=C1C1=NC(C(F)(F)F)=CN1 STJRPFWQLMFZBE-UHFFFAOYSA-N 0.000 description 2
- BFJNWLVWNVUBOH-UHFFFAOYSA-N 5-[2-[benzyl-[3-(4-formylphenoxy)-2-hydroxypropyl]amino]ethoxy]-2-phenylmethoxybenzamide Chemical compound C=1C=C(OCC=2C=CC=CC=2)C(C(=O)N)=CC=1OCCN(CC=1C=CC=CC=1)CC(O)COC1=CC=C(C=O)C=C1 BFJNWLVWNVUBOH-UHFFFAOYSA-N 0.000 description 2
- CQVWWWOYXZRGTA-UHFFFAOYSA-N 5-[2-[benzyl-[3-[4-(4,6-dimethylpyrimidin-2-yl)phenoxy]-2-hydroxypropyl]amino]ethoxy]-2-hydroxybenzamide;hydrochloride Chemical compound Cl.CC1=CC(C)=NC(C=2C=CC(OCC(O)CN(CCOC=3C=C(C(O)=CC=3)C(N)=O)CC=3C=CC=CC=3)=CC=2)=N1 CQVWWWOYXZRGTA-UHFFFAOYSA-N 0.000 description 2
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
- 239000005695 Ammonium acetate Substances 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- 239000004470 DL Methionine Substances 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 2
- 229930195722 L-methionine Natural products 0.000 description 2
- 229930195725 Mannitol Natural products 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- AIJULSRZWUXGPQ-UHFFFAOYSA-N Methylglyoxal Chemical compound CC(=O)C=O AIJULSRZWUXGPQ-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 208000001871 Tachycardia Diseases 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
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 230000002730 additional effect Effects 0.000 description 2
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 125000005115 alkyl carbamoyl group Chemical group 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
- 150000001412 amines Chemical class 0.000 description 2
- 235000019257 ammonium acetate Nutrition 0.000 description 2
- 229940043376 ammonium acetate Drugs 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 125000003435 aroyl group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical group C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- CPUHFNXAASGWCL-UHFFFAOYSA-N diethyl 4-(4-hydroxyphenyl)-2,6-dimethylpyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C)N=C(C)C(C(=O)OCC)=C1C1=CC=C(O)C=C1 CPUHFNXAASGWCL-UHFFFAOYSA-N 0.000 description 2
- INBDZZNVIFHONQ-UHFFFAOYSA-N diethyl 4-[4-[3-[benzyl-[2-(3-carbamoyl-4-hydroxyphenoxy)ethyl]amino]-2-hydroxypropoxy]phenyl]-2,6-dimethylpyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C)N=C(C)C(C(=O)OCC)=C1C(C=C1)=CC=C1OCC(O)CN(CC=1C=CC=CC=1)CCOC1=CC=C(O)C(C(N)=O)=C1 INBDZZNVIFHONQ-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229940093915 gynecological organic acid Drugs 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N hydroxymethyl benzene Natural products OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
- 229960001317 isoprenaline Drugs 0.000 description 2
- FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 2
- 229940039009 isoproterenol Drugs 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000001630 malic acid Substances 0.000 description 2
- 235000011090 malic acid Nutrition 0.000 description 2
- 239000000594 mannitol Substances 0.000 description 2
- 235000010355 mannitol Nutrition 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- 229930182817 methionine Natural products 0.000 description 2
- 235000006109 methionine Nutrition 0.000 description 2
- 229960004452 methionine Drugs 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 235000019260 propionic acid Nutrition 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
- 229960004889 salicylic acid Drugs 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 230000004936 stimulating effect Effects 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 230000006794 tachycardia Effects 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- NNJPGOLRFBJNIW-HNNXBMFYSA-N (-)-demecolcine Chemical compound C1=C(OC)C(=O)C=C2[C@@H](NC)CCC3=CC(OC)=C(OC)C(OC)=C3C2=C1 NNJPGOLRFBJNIW-HNNXBMFYSA-N 0.000 description 1
- XPNGNIFUDRPBFJ-UHFFFAOYSA-N (2-methylphenyl)methanol Chemical compound CC1=CC=CC=C1CO XPNGNIFUDRPBFJ-UHFFFAOYSA-N 0.000 description 1
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- QNYBOILAKBSWFG-SNVBAGLBSA-N (2s)-2-(phenylmethoxymethyl)oxirane Chemical compound C([C@H]1OC1)OCC1=CC=CC=C1 QNYBOILAKBSWFG-SNVBAGLBSA-N 0.000 description 1
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
- AAWZDTNXLSGCEK-LNVDRNJUSA-N (3r,5r)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid Chemical compound O[C@@H]1CC(O)(C(O)=O)C[C@@H](O)C1O AAWZDTNXLSGCEK-LNVDRNJUSA-N 0.000 description 1
- BMFNDMNRYPFUPF-HWKANZROSA-N (E)-4-hydroxy-3-nitrosopent-3-en-2-one Chemical compound C\C(O)=C(/N=O)C(C)=O BMFNDMNRYPFUPF-HWKANZROSA-N 0.000 description 1
- UWYVPFMHMJIBHE-OWOJBTEDSA-N (e)-2-hydroxybut-2-enedioic acid Chemical compound OC(=O)\C=C(\O)C(O)=O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
- SHXHPUAKLCCLDV-UHFFFAOYSA-N 1,1,1-trifluoropentane-2,4-dione Chemical compound CC(=O)CC(=O)C(F)(F)F SHXHPUAKLCCLDV-UHFFFAOYSA-N 0.000 description 1
- ZABBFAHZPHMIJC-UHFFFAOYSA-N 1,1-Dibromopropan-2-one Chemical compound CC(=O)C(Br)Br ZABBFAHZPHMIJC-UHFFFAOYSA-N 0.000 description 1
- 125000004814 1,1-dimethylethylene group Chemical group [H]C([H])([H])C([*:1])(C([H])([H])[H])C([H])([H])[*:2] 0.000 description 1
- 125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 description 1
- YWHXNULGCMEIGW-UHFFFAOYSA-N 1,2-dimethyl-5-(3-phenylmethoxyphenyl)pyrrole Chemical compound CN1C(C)=CC=C1C1=CC=CC(OCC=2C=CC=CC=2)=C1 YWHXNULGCMEIGW-UHFFFAOYSA-N 0.000 description 1
- UBJBUXHOJVGNIR-UHFFFAOYSA-N 1,4,5-trimethyl-2-[4-(oxiran-2-ylmethoxy)phenyl]imidazole Chemical compound CN1C(C)=C(C)N=C1C(C=C1)=CC=C1OCC1OC1 UBJBUXHOJVGNIR-UHFFFAOYSA-N 0.000 description 1
- VLXSIHLNPYRFFN-UHFFFAOYSA-N 1,4-dioxane;methanol Chemical compound OC.C1COCCO1 VLXSIHLNPYRFFN-UHFFFAOYSA-N 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- OKONOECBBCKOMC-UHFFFAOYSA-N 1-(dibenzylamino)-3-[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenoxy]propan-2-ol Chemical compound CN1C=C(C(F)(F)F)N=C1C(C=C1)=CC=C1OCC(O)CN(CC=1C=CC=CC=1)CC1=CC=CC=C1 OKONOECBBCKOMC-UHFFFAOYSA-N 0.000 description 1
- QGCKEPAARLSDES-UHFFFAOYSA-N 1-[2-(4-hydroxyphenyl)-1,5-dimethylimidazol-4-yl]ethanone Chemical compound CN1C(C)=C(C(=O)C)N=C1C1=CC=C(O)C=C1 QGCKEPAARLSDES-UHFFFAOYSA-N 0.000 description 1
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- MKSUBNAQKGYXKX-UHFFFAOYSA-N 1-benzyl-2-[5-[4-(oxiran-2-ylmethoxy)phenyl]furan-2-yl]-4-(trifluoromethyl)imidazole Chemical compound C=1C=C(C=2C=CC(OCC3OC3)=CC=2)OC=1C1=NC(C(F)(F)F)=CN1CC1=CC=CC=C1 MKSUBNAQKGYXKX-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- DJMZGUMHNYNBPZ-UHFFFAOYSA-N 1-methyl-3-[4-(oxiran-2-ylmethoxy)phenyl]-5-(trifluoromethyl)-1,2,4-triazole Chemical compound N1=C(C(F)(F)F)N(C)N=C1C(C=C1)=CC=C1OCC1OC1 DJMZGUMHNYNBPZ-UHFFFAOYSA-N 0.000 description 1
- DANNNYVUDVZLRC-UHFFFAOYSA-N 1-methyl-3-methylsulfonyl-5-[4-(oxiran-2-ylmethoxy)phenyl]-1,2,4-triazole Chemical compound CN1N=C(S(C)(=O)=O)N=C1C(C=C1)=CC=C1OCC1OC1 DANNNYVUDVZLRC-UHFFFAOYSA-N 0.000 description 1
- LYFNAJACLPGPIK-UHFFFAOYSA-N 1-methyl-4-(trifluoromethyl)imidazole Chemical compound CN1C=NC(C(F)(F)F)=C1 LYFNAJACLPGPIK-UHFFFAOYSA-N 0.000 description 1
- UYHNSBLTTYCFAE-UHFFFAOYSA-N 1-methyl-6-[4-(oxiran-2-ylmethoxy)phenyl]-3,4-dihydropyridin-2-one Chemical compound CN1C(=O)CCC=C1C(C=C1)=CC=C1OCC1OC1 UYHNSBLTTYCFAE-UHFFFAOYSA-N 0.000 description 1
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
- OFUCCBIWEUKISP-UHFFFAOYSA-N 2,2,2-trifluoroacetohydrazide Chemical compound NNC(=O)C(F)(F)F OFUCCBIWEUKISP-UHFFFAOYSA-N 0.000 description 1
- JFZAJWBGISKERI-UHFFFAOYSA-N 2,4-dihydroxybenzonitrile Chemical compound OC1=CC=C(C#N)C(O)=C1 JFZAJWBGISKERI-UHFFFAOYSA-N 0.000 description 1
- UFBJCMHMOXMLKC-UHFFFAOYSA-N 2,4-dinitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O UFBJCMHMOXMLKC-UHFFFAOYSA-N 0.000 description 1
- APGLXTXFTYAQKC-UHFFFAOYSA-N 2,5-dihydroxybenzonitrile Chemical compound OC1=CC=C(O)C(C#N)=C1 APGLXTXFTYAQKC-UHFFFAOYSA-N 0.000 description 1
- BJYYITKHIQLSFZ-UHFFFAOYSA-N 2-(4-hydroxyphenyl)-3,6-dimethylpyrimidin-4-one Chemical compound CC1=CC(=O)N(C)C(C=2C=CC(O)=CC=2)=N1 BJYYITKHIQLSFZ-UHFFFAOYSA-N 0.000 description 1
- KJMXVHBTWJSSBL-UHFFFAOYSA-N 2-(trifluoromethyl)-1h-imidazole Chemical compound FC(F)(F)C1=NC=CN1 KJMXVHBTWJSSBL-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- UYGNFKCUOSYRQR-UHFFFAOYSA-N 2-[(2,2-dimethyl-4-oxo-3h-1,3-benzoxazin-7-yl)oxy]acetaldehyde Chemical compound C1=C(OCC=O)C=C2OC(C)(C)NC(=O)C2=C1 UYGNFKCUOSYRQR-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- DBRUXNYZLPAPBZ-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)phenyl]-1h-indole Chemical compound C=1C=CC=C(C=2NC3=CC=CC=C3C=2)C=1OCC1CO1 DBRUXNYZLPAPBZ-UHFFFAOYSA-N 0.000 description 1
- GLXXHIYRLWANMY-UHFFFAOYSA-N 2-[2-[4-(oxiran-2-ylmethoxy)phenyl]-4-(trifluoromethyl)imidazol-1-yl]ethanol Chemical compound OCCN1C=C(C(F)(F)F)N=C1C(C=C1)=CC=C1OCC1OC1 GLXXHIYRLWANMY-UHFFFAOYSA-N 0.000 description 1
- APCXIEMPUFXCBZ-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)phenyl]-1-propan-2-yl-4-(trifluoromethyl)imidazole Chemical compound CC(C)N1C=C(C(F)(F)F)N=C1C(C=C1)=CC=C1OCC1OC1 APCXIEMPUFXCBZ-UHFFFAOYSA-N 0.000 description 1
- ODRIDSWZAYARNY-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)phenyl]-5-(trifluoromethyl)-1h-imidazole Chemical compound FC(F)(F)C1=CNC(C=2C=CC(OCC3OC3)=CC=2)=N1 ODRIDSWZAYARNY-UHFFFAOYSA-N 0.000 description 1
- CVNMLFSMDXPBEY-UHFFFAOYSA-N 2-[5-(4-methoxyphenyl)furan-2-yl]-5-(trifluoromethyl)-1h-imidazole Chemical compound C1=CC(OC)=CC=C1C1=CC=C(C=2NC=C(N=2)C(F)(F)F)O1 CVNMLFSMDXPBEY-UHFFFAOYSA-N 0.000 description 1
- IQKXDNWXSCXSKF-UHFFFAOYSA-N 2-hydroperoxybenzamide Chemical compound NC(=O)C1=CC=CC=C1OO IQKXDNWXSCXSKF-UHFFFAOYSA-N 0.000 description 1
- HNXBQEBLXZOCBE-UHFFFAOYSA-N 2-hydroperoxybenzonitrile Chemical compound OOC1=CC=CC=C1C#N HNXBQEBLXZOCBE-UHFFFAOYSA-N 0.000 description 1
- UDFZIBHLMVLNAO-UHFFFAOYSA-N 2-hydroxy-4-[2-[[2-hydroxy-3-[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenoxy]propyl]amino]ethoxy]benzamide Chemical compound CN1C=C(C(F)(F)F)N=C1C(C=C1)=CC=C1OCC(O)CNCCOC1=CC=C(C(N)=O)C(O)=C1 UDFZIBHLMVLNAO-UHFFFAOYSA-N 0.000 description 1
- QTKGGSMALHCAKN-UHFFFAOYSA-N 2-hydroxy-5-(2-oxopropoxy)benzamide Chemical compound CC(=O)COC1=CC=C(O)C(C(N)=O)=C1 QTKGGSMALHCAKN-UHFFFAOYSA-N 0.000 description 1
- DPNPLQIDQVFGCD-UHFFFAOYSA-N 2-hydroxy-5-[2-[[2-hydroxy-3-(4-phenylphenoxy)propyl]amino]ethoxy]benzamide Chemical compound C1=C(O)C(C(=O)N)=CC(OCCNCC(O)COC=2C=CC(=CC=2)C=2C=CC=CC=2)=C1 DPNPLQIDQVFGCD-UHFFFAOYSA-N 0.000 description 1
- NBHWMHJBLAGFJM-UHFFFAOYSA-N 2-hydroxy-5-[2-[[2-hydroxy-3-[2-(1h-indol-2-yl)phenoxy]propyl]amino]ethoxy]benzamide Chemical compound C1=C(O)C(C(=O)N)=CC(OCCNCC(O)COC=2C(=CC=CC=2)C=2NC3=CC=CC=C3C=2)=C1 NBHWMHJBLAGFJM-UHFFFAOYSA-N 0.000 description 1
- PMRBTTTXVWQKMF-UHFFFAOYSA-N 2-hydroxy-5-[2-[[2-hydroxy-3-[4-(1,3-thiazol-2-yl)phenoxy]propyl]amino]ethoxy]benzamide Chemical compound C1=C(O)C(C(=O)N)=CC(OCCNCC(O)COC=2C=CC(=CC=2)C=2SC=CN=2)=C1 PMRBTTTXVWQKMF-UHFFFAOYSA-N 0.000 description 1
- OEFVDLWBRJIWSB-UHFFFAOYSA-N 2-hydroxy-5-[2-[[2-hydroxy-3-[4-(1,4,5-trimethylimidazol-2-yl)phenoxy]propyl]amino]ethoxy]benzamide Chemical compound CN1C(C)=C(C)N=C1C(C=C1)=CC=C1OCC(O)CNCCOC1=CC=C(O)C(C(N)=O)=C1 OEFVDLWBRJIWSB-UHFFFAOYSA-N 0.000 description 1
- HPNFYVITJHBTPY-UHFFFAOYSA-N 2-hydroxy-5-[2-[[2-hydroxy-3-[4-(1-methylimidazol-2-yl)phenoxy]propyl]amino]ethoxy]benzamide Chemical compound CN1C=CN=C1C(C=C1)=CC=C1OCC(O)CNCCOC1=CC=C(O)C(C(N)=O)=C1 HPNFYVITJHBTPY-UHFFFAOYSA-N 0.000 description 1
- JDMXMURJERPYDV-UHFFFAOYSA-N 2-hydroxy-5-[2-[[2-hydroxy-3-[4-(2-methyl-5-methylsulfanyl-1,2,4-triazol-3-yl)phenoxy]propyl]amino]ethoxy]benzamide Chemical compound CN1N=C(SC)N=C1C(C=C1)=CC=C1OCC(O)CNCCOC1=CC=C(O)C(C(N)=O)=C1 JDMXMURJERPYDV-UHFFFAOYSA-N 0.000 description 1
- HQQYWGLNXUTNNL-UHFFFAOYSA-N 2-hydroxy-5-[2-[[2-hydroxy-3-[4-(4-methyl-5-methylsulfanyl-1,2,4-triazol-3-yl)phenoxy]propyl]amino]ethoxy]benzamide Chemical compound CN1C(SC)=NN=C1C(C=C1)=CC=C1OCC(O)CNCCOC1=CC=C(O)C(C(N)=O)=C1 HQQYWGLNXUTNNL-UHFFFAOYSA-N 0.000 description 1
- LHYAYUCVGFWPPH-UHFFFAOYSA-N 2-hydroxy-5-[2-[[2-hydroxy-3-[4-[1-(2-hydroxyethyl)-4-(trifluoromethyl)imidazol-2-yl]phenoxy]propyl]amino]ethoxy]benzamide Chemical compound C1=C(O)C(C(=O)N)=CC(OCCNCC(O)COC=2C=CC(=CC=2)C=2N(C=C(N=2)C(F)(F)F)CCO)=C1 LHYAYUCVGFWPPH-UHFFFAOYSA-N 0.000 description 1
- WCGFVHTXHGTOBW-UHFFFAOYSA-N 2-hydroxy-5-[2-[[2-hydroxy-3-[4-[1-methyl-4-(trifluoromethyl)imidazol-2-yl]phenoxy]propyl]amino]ethoxy]benzoic acid Chemical compound CN1C=C(C(F)(F)F)N=C1C(C=C1)=CC=C1OCC(O)CNCCOC1=CC=C(O)C(C(O)=O)=C1 WCGFVHTXHGTOBW-UHFFFAOYSA-N 0.000 description 1
- PLLNEKMHQROMIL-UHFFFAOYSA-N 2-hydroxy-5-[2-[[2-hydroxy-3-[4-[1-methyl-5-(trifluoromethyl)imidazol-2-yl]phenoxy]propyl]amino]ethoxy]benzamide Chemical compound C1=C(C(F)(F)F)N(C)C(C=2C=CC(OCC(O)CNCCOC=3C=C(C(O)=CC=3)C(N)=O)=CC=2)=N1 PLLNEKMHQROMIL-UHFFFAOYSA-N 0.000 description 1
- XTFDCJNUZOXVOS-UHFFFAOYSA-N 2-hydroxy-5-[2-[[2-hydroxy-3-[4-[1-propan-2-yl-4-(trifluoromethyl)imidazol-2-yl]phenoxy]propyl]amino]ethoxy]benzamide Chemical compound CC(C)N1C=C(C(F)(F)F)N=C1C(C=C1)=CC=C1OCC(O)CNCCOC1=CC=C(O)C(C(N)=O)=C1 XTFDCJNUZOXVOS-UHFFFAOYSA-N 0.000 description 1
- QRTRFYBBFGCANR-UHFFFAOYSA-N 2-hydroxy-5-[2-[[2-hydroxy-3-[4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]phenoxy]propyl]amino]ethoxy]benzamide Chemical compound C1=C(O)C(C(=O)N)=CC(OCCNCC(O)COC=2C=CC(=CC=2)C=2SC=C(N=2)C(F)(F)F)=C1 QRTRFYBBFGCANR-UHFFFAOYSA-N 0.000 description 1
- CEWNRHDBEKBIOB-UHFFFAOYSA-N 2-hydroxy-5-[2-[[2-hydroxy-3-[4-[4-methyl-5-(trifluoromethyl)-1,2,4-triazol-3-yl]phenoxy]propyl]amino]ethoxy]benzamide Chemical compound N1=C(C(F)(F)F)N(C)C(C=2C=CC(OCC(O)CNCCOC=3C=C(C(O)=CC=3)C(N)=O)=CC=2)=N1 CEWNRHDBEKBIOB-UHFFFAOYSA-N 0.000 description 1
- GXVHRJQHAPPVBI-UHFFFAOYSA-N 2-hydroxy-5-[2-[[2-hydroxy-3-[4-[5-[5-(trifluoromethyl)-1h-imidazol-2-yl]furan-2-yl]phenoxy]propyl]amino]ethoxy]benzamide;methanesulfonic acid Chemical compound CS(O)(=O)=O.CS(O)(=O)=O.C1=C(O)C(C(=O)N)=CC(OCCNCC(O)COC=2C=CC(=CC=2)C=2OC(=CC=2)C=2NC=C(N=2)C(F)(F)F)=C1 GXVHRJQHAPPVBI-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- QSECPQCFCWVBKM-UHFFFAOYSA-N 2-iodoethanol Chemical compound OCCI QSECPQCFCWVBKM-UHFFFAOYSA-N 0.000 description 1
- GIYXGSBLEQOCDW-UHFFFAOYSA-N 3,6-dimethyl-2-(4-phenylmethoxyphenyl)pyrimidin-4-one Chemical compound CC1=CC(=O)N(C)C(C=2C=CC(OCC=3C=CC=CC=3)=CC=2)=N1 GIYXGSBLEQOCDW-UHFFFAOYSA-N 0.000 description 1
- SOBMEHHJKCZLLB-UHFFFAOYSA-N 3-(4-methoxyphenyl)-1-methyl-5-(trifluoromethyl)-1,2,4-triazole Chemical compound C1=CC(OC)=CC=C1C1=NN(C)C(C(F)(F)F)=N1 SOBMEHHJKCZLLB-UHFFFAOYSA-N 0.000 description 1
- PPSHEHNBABGTTJ-UHFFFAOYSA-N 3-(4-methoxyphenyl)-4-methyl-5-(trifluoromethyl)-1,2,4-triazole Chemical compound C1=CC(OC)=CC=C1C1=NN=C(C(F)(F)F)N1C PPSHEHNBABGTTJ-UHFFFAOYSA-N 0.000 description 1
- JJNVTOZYUABEKT-UHFFFAOYSA-N 3-(4-methoxyphenyl)-4-methyl-5-methylsulfanyl-1,2,4-triazole Chemical compound C1=CC(OC)=CC=C1C1=NN=C(SC)N1C JJNVTOZYUABEKT-UHFFFAOYSA-N 0.000 description 1
- ONZQYZKCUHFORE-UHFFFAOYSA-N 3-bromo-1,1,1-trifluoropropan-2-one Chemical compound FC(F)(F)C(=O)CBr ONZQYZKCUHFORE-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- JAICGBJIBWDEIZ-UHFFFAOYSA-N 3-phenylmethoxybenzaldehyde Chemical compound O=CC1=CC=CC(OCC=2C=CC=CC=2)=C1 JAICGBJIBWDEIZ-UHFFFAOYSA-N 0.000 description 1
- SBNYJIXVLUCVHQ-UHFFFAOYSA-N 4-(1,4,5-trimethylimidazol-2-yl)phenol Chemical compound CN1C(C)=C(C)N=C1C1=CC=C(O)C=C1 SBNYJIXVLUCVHQ-UHFFFAOYSA-N 0.000 description 1
- QPGQVCJPXFVILX-UHFFFAOYSA-N 4-(2-methyl-5-methylsulfanyl-1,2,4-triazol-3-yl)phenol Chemical compound CN1N=C(SC)N=C1C1=CC=C(O)C=C1 QPGQVCJPXFVILX-UHFFFAOYSA-N 0.000 description 1
- DHVYVFDSGOTDPA-UHFFFAOYSA-N 4-(2-methyltetrazol-5-yl)phenol Chemical compound CN1N=NC(C=2C=CC(O)=CC=2)=N1 DHVYVFDSGOTDPA-UHFFFAOYSA-N 0.000 description 1
- RDIZSICWGUQOTD-UHFFFAOYSA-N 4-(4,6-dimethylpyrimidin-2-yl)phenol Chemical compound CC1=CC(C)=NC(C=2C=CC(O)=CC=2)=N1 RDIZSICWGUQOTD-UHFFFAOYSA-N 0.000 description 1
- VAKABUBSGYOQIM-UHFFFAOYSA-N 4-(oxiran-2-ylmethoxy)benzaldehyde Chemical compound C1=CC(C=O)=CC=C1OCC1OC1 VAKABUBSGYOQIM-UHFFFAOYSA-N 0.000 description 1
- BKDUWMJFLCNPKP-UHFFFAOYSA-N 4-(trifluoromethyl)pyrimidine Chemical compound FC(F)(F)C1=CC=NC=N1 BKDUWMJFLCNPKP-UHFFFAOYSA-N 0.000 description 1
- JWVSEEHWQYTEQW-UHFFFAOYSA-N 4-[1-methyl-5-(trifluoromethyl)-1,2,4-triazol-3-yl]phenol Chemical compound N1=C(C(F)(F)F)N(C)N=C1C1=CC=C(O)C=C1 JWVSEEHWQYTEQW-UHFFFAOYSA-N 0.000 description 1
- QKJWIRPYFRHCBR-UHFFFAOYSA-N 4-[1-propan-2-yl-4-(trifluoromethyl)imidazol-2-yl]phenol Chemical compound CC(C)N1C=C(C(F)(F)F)N=C1C1=CC=C(O)C=C1 QKJWIRPYFRHCBR-UHFFFAOYSA-N 0.000 description 1
- KKFMOLKCLFEIMH-UHFFFAOYSA-N 4-[1-propan-2-yl-5-(trifluoromethyl)imidazol-2-yl]phenol Chemical compound C1=C(C(F)(F)F)N(C(C)C)C(C=2C=CC(O)=CC=2)=N1 KKFMOLKCLFEIMH-UHFFFAOYSA-N 0.000 description 1
- RZUYCHLTCASODF-UHFFFAOYSA-N 4-[4-methyl-5-(trifluoromethyl)-1,2,4-triazol-3-yl]phenol Chemical compound N1=C(C(F)(F)F)N(C)C(C=2C=CC(O)=CC=2)=N1 RZUYCHLTCASODF-UHFFFAOYSA-N 0.000 description 1
- OZZFZUDQGFQJNL-UHFFFAOYSA-N 4-[4-methyl-6-(trifluoromethyl)pyrimidin-2-yl]phenol Chemical compound CC1=CC(C(F)(F)F)=NC(C=2C=CC(O)=CC=2)=N1 OZZFZUDQGFQJNL-UHFFFAOYSA-N 0.000 description 1
- ALYNCZNDIQEVRV-PZFLKRBQSA-N 4-amino-3,5-ditritiobenzoic acid Chemical compound [3H]c1cc(cc([3H])c1N)C(O)=O ALYNCZNDIQEVRV-PZFLKRBQSA-N 0.000 description 1
- PXACTUVBBMDKRW-UHFFFAOYSA-N 4-bromobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Br)C=C1 PXACTUVBBMDKRW-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- KATOTACQUVLLMV-UHFFFAOYSA-N 4-hydroxybenzenecarboximidamide dihydrate Chemical compound O.O.NC(=N)C1=CC=C(O)C=C1 KATOTACQUVLLMV-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- ZQOBPLVIIXZIGJ-UHFFFAOYSA-N 4-methyl-3-[4-(oxiran-2-ylmethoxy)phenyl]-5-(trifluoromethyl)-1,2,4-triazole Chemical compound N1=C(C(F)(F)F)N(C)C(C=2C=CC(OCC3OC3)=CC=2)=N1 ZQOBPLVIIXZIGJ-UHFFFAOYSA-N 0.000 description 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-M 4-nitrophenolate Chemical compound [O-]C1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-M 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical compound [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 description 1
- KWBNVKBWZBMYMA-UHFFFAOYSA-N 5-(2-bromoethoxy)-2-hydroxybenzamide Chemical compound NC(=O)C1=CC(OCCBr)=CC=C1O KWBNVKBWZBMYMA-UHFFFAOYSA-N 0.000 description 1
- DXNWPGHSUNATDB-UHFFFAOYSA-N 5-(4-methoxyphenyl)-1-methyl-3-methylsulfanyl-1,2,4-triazole Chemical compound C1=CC(OC)=CC=C1C1=NC(SC)=NN1C DXNWPGHSUNATDB-UHFFFAOYSA-N 0.000 description 1
- GAXSJNOMPGKADC-UHFFFAOYSA-N 5-(4-methoxyphenyl)-2-methyltetrazole Chemical compound C1=CC(OC)=CC=C1C1=NN(C)N=N1 GAXSJNOMPGKADC-UHFFFAOYSA-N 0.000 description 1
- KZGGHPBTKGLWQL-UHFFFAOYSA-N 5-(4-methoxyphenyl)-2h-tetrazole Chemical compound C1=CC(OC)=CC=C1C1=NNN=N1 KZGGHPBTKGLWQL-UHFFFAOYSA-N 0.000 description 1
- YBQCXCGERNATCE-UHFFFAOYSA-N 5-[2-(benzylamino)ethoxy]-2-phenylmethoxybenzamide Chemical compound C=1C=C(OCC=2C=CC=CC=2)C(C(=O)N)=CC=1OCCNCC1=CC=CC=C1 YBQCXCGERNATCE-UHFFFAOYSA-N 0.000 description 1
- RTWWLFMMYOUHGA-UHFFFAOYSA-N 5-[2-[[3-[4-(1,4-dimethyl-6-oxopyrimidin-2-yl)oxyphenoxy]-2-hydroxypropyl]amino]ethoxy]-2-hydroxybenzamide Chemical compound CC1=CC(=O)N(C)C(OC=2C=CC(OCC(O)CNCCOC=3C=C(C(O)=CC=3)C(N)=O)=CC=2)=N1 RTWWLFMMYOUHGA-UHFFFAOYSA-N 0.000 description 1
- TWQKYEBBVUSULK-UHFFFAOYSA-N 5-[2-[[3-[4-(1,4-dimethyl-6-oxopyrimidin-2-yl)phenoxy]-2-hydroxypropyl]amino]ethoxy]-2-hydroxybenzamide;hydrochloride Chemical compound Cl.CC1=CC(=O)N(C)C(C=2C=CC(OCC(O)CNCCOC=3C=C(C(O)=CC=3)C(N)=O)=CC=2)=N1 TWQKYEBBVUSULK-UHFFFAOYSA-N 0.000 description 1
- WFKAIIHBJOBRIK-UHFFFAOYSA-N 5-[2-[[3-[4-(4,6-dimethylpyrimidin-2-yl)phenoxy]-2-hydroxypropyl]amino]ethoxy]-2-hydroxybenzamide Chemical compound CC1=CC(C)=NC(C=2C=CC(OCC(O)CNCCOC=3C=C(C(O)=CC=3)C(N)=O)=CC=2)=N1 WFKAIIHBJOBRIK-UHFFFAOYSA-N 0.000 description 1
- QIXOOOMMPXIEQL-UHFFFAOYSA-N 5-[2-[benzyl-[2-hydroxy-3-[4-(1,4,5-trimethylimidazol-2-yl)phenoxy]propyl]amino]ethoxy]-2-hydroxybenzamide Chemical compound CN1C(C)=C(C)N=C1C(C=C1)=CC=C1OCC(O)CN(CC=1C=CC=CC=1)CCOC1=CC=C(O)C(C(N)=O)=C1 QIXOOOMMPXIEQL-UHFFFAOYSA-N 0.000 description 1
- ISYAEZHKGCDOLV-UHFFFAOYSA-N 5-[2-[benzyl-[2-hydroxy-3-[4-(1-methyl-2-oxo-3,4-dihydropyridin-6-yl)phenoxy]propyl]amino]ethoxy]-2-hydroxybenzamide Chemical compound CN1C(=O)CCC=C1C(C=C1)=CC=C1OCC(O)CN(CC=1C=CC=CC=1)CCOC1=CC=C(O)C(C(N)=O)=C1 ISYAEZHKGCDOLV-UHFFFAOYSA-N 0.000 description 1
- PIVJGTWNFQCXEP-UHFFFAOYSA-N 5-[2-[benzyl-[2-hydroxy-3-[4-(1h-imidazol-2-yl)phenoxy]propyl]amino]ethoxy]-2-phenylmethoxybenzamide Chemical compound C=1C=C(OCC=2C=CC=CC=2)C(C(=O)N)=CC=1OCCN(CC=1C=CC=CC=1)CC(O)COC(C=C1)=CC=C1C1=NC=CN1 PIVJGTWNFQCXEP-UHFFFAOYSA-N 0.000 description 1
- GUGZVUONRXQZIQ-UHFFFAOYSA-N 5-[2-[benzyl-[2-hydroxy-3-[4-(2-methyl-5-methylsulfonyl-1,2,4-triazol-3-yl)phenoxy]propyl]amino]ethoxy]-2-hydroxybenzamide Chemical compound CN1N=C(S(C)(=O)=O)N=C1C(C=C1)=CC=C1OCC(O)CN(CC=1C=CC=CC=1)CCOC1=CC=C(O)C(C(N)=O)=C1 GUGZVUONRXQZIQ-UHFFFAOYSA-N 0.000 description 1
- WRVKDZKHTVAXPQ-UHFFFAOYSA-N 5-[2-[benzyl-[2-hydroxy-3-[4-(5-methyl-1h-imidazol-2-yl)phenoxy]propyl]amino]ethoxy]-2-phenylmethoxybenzamide Chemical compound N1C(C)=CN=C1C(C=C1)=CC=C1OCC(O)CN(CC=1C=CC=CC=1)CCOC(C=C1C(N)=O)=CC=C1OCC1=CC=CC=C1 WRVKDZKHTVAXPQ-UHFFFAOYSA-N 0.000 description 1
- PMUHFZIJQSKHLV-UHFFFAOYSA-N 5-[2-[benzyl-[2-hydroxy-3-[4-[1-(2-hydroxyethyl)-4-(trifluoromethyl)imidazol-2-yl]phenoxy]propyl]amino]ethoxy]-2-hydroxybenzamide Chemical compound C1=C(O)C(C(=O)N)=CC(OCCN(CC(O)COC=2C=CC(=CC=2)C=2N(C=C(N=2)C(F)(F)F)CCO)CC=2C=CC=CC=2)=C1 PMUHFZIJQSKHLV-UHFFFAOYSA-N 0.000 description 1
- CTRMEUPPNSRUMU-UHFFFAOYSA-N 5-[2-[benzyl-[2-hydroxy-3-[4-[1-propan-2-yl-4-(trifluoromethyl)imidazol-2-yl]phenoxy]propyl]amino]ethoxy]-2-hydroxybenzamide Chemical compound CC(C)N1C=C(C(F)(F)F)N=C1C(C=C1)=CC=C1OCC(O)CN(CC=1C=CC=CC=1)CCOC1=CC=C(O)C(C(N)=O)=C1 CTRMEUPPNSRUMU-UHFFFAOYSA-N 0.000 description 1
- YXWLAYFUVJYZSG-UHFFFAOYSA-N 5-[2-[benzyl-[3-(4-formylphenoxy)-2-hydroxypropyl]amino]ethoxy]-2-phenylmethoxybenzamide;hydrochloride Chemical compound Cl.C=1C=C(OCC=2C=CC=CC=2)C(C(=O)N)=CC=1OCCN(CC=1C=CC=CC=1)CC(O)COC1=CC=C(C=O)C=C1 YXWLAYFUVJYZSG-UHFFFAOYSA-N 0.000 description 1
- JRVGWXWOSMJISK-UHFFFAOYSA-N 5-[2-[benzyl-[3-[4-(1,4-dimethyl-6-oxopyrimidin-2-yl)phenoxy]-2-hydroxypropyl]amino]ethoxy]-2-hydroxybenzamide Chemical compound CC1=CC(=O)N(C)C(C=2C=CC(OCC(O)CN(CCOC=3C=C(C(O)=CC=3)C(N)=O)CC=3C=CC=CC=3)=CC=2)=N1 JRVGWXWOSMJISK-UHFFFAOYSA-N 0.000 description 1
- WRDRHQYEPMVCND-UHFFFAOYSA-N 5-ethoxycarbonyl-4-(4-hydroxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3-carboxylic acid Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=C(O)C=C1 WRDRHQYEPMVCND-UHFFFAOYSA-N 0.000 description 1
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- AAWZDTNXLSGCEK-UHFFFAOYSA-N Cordycepinsaeure Natural products OC1CC(O)(C(O)=O)CC(O)C1O AAWZDTNXLSGCEK-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- 206010020850 Hyperthyroidism Diseases 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 244000151018 Maranta arundinacea Species 0.000 description 1
- 235000010804 Maranta arundinacea Nutrition 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- AAWZDTNXLSGCEK-ZHQZDSKASA-N Quinic acid Natural products O[C@H]1CC(O)(C(O)=O)C[C@H](O)C1O AAWZDTNXLSGCEK-ZHQZDSKASA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 1
- SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical class NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 235000012419 Thalia geniculata Nutrition 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- ONGFJRWRRYOMSC-UHFFFAOYSA-N [1-[2-(3-carbamoyl-4-hydroxyphenoxy)ethylamino]-3-[4-[1-methyl-5-(trifluoromethyl)imidazol-2-yl]phenoxy]propan-2-yl] methanesulfonate Chemical compound C1=C(C(F)(F)F)N(C)C(C=2C=CC(OCC(CNCCOC=3C=C(C(O)=CC=3)C(N)=O)OS(C)(=O)=O)=CC=2)=N1 ONGFJRWRRYOMSC-UHFFFAOYSA-N 0.000 description 1
- CKUAXEQHGKSLHN-UHFFFAOYSA-N [C].[N] Chemical compound [C].[N] CKUAXEQHGKSLHN-UHFFFAOYSA-N 0.000 description 1
- 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 1
- DDQAGDLHARKUFX-UHFFFAOYSA-N acetic acid;methanamine Chemical compound [NH3+]C.CC([O-])=O DDQAGDLHARKUFX-UHFFFAOYSA-N 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000001800 adrenalinergic effect Effects 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000001365 aminolytic effect Effects 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000004872 arterial blood pressure Effects 0.000 description 1
- 125000005101 aryl methoxy carbonyl group Chemical group 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229940095076 benzaldehyde Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229960004365 benzoic acid Drugs 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 208000006218 bradycardia Diseases 0.000 description 1
- 230000036471 bradycardia Effects 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- HCVIFQKNRBHTAC-UHFFFAOYSA-N chembl1425128 Chemical compound CN1C(SC)=NN=C1C1=CC=C(O)C=C1 HCVIFQKNRBHTAC-UHFFFAOYSA-N 0.000 description 1
- PXNRJZLHXKIISI-UHFFFAOYSA-N chembl2131269 Chemical compound C1=CC(O)=CC=C1C1=NC=CS1 PXNRJZLHXKIISI-UHFFFAOYSA-N 0.000 description 1
- VDTNKXSVUGXUOJ-UHFFFAOYSA-N chembl2441358 Chemical compound NC(=S)C1=CC=C(O)C=C1 VDTNKXSVUGXUOJ-UHFFFAOYSA-N 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- UZEDIBTVIIJELN-UHFFFAOYSA-N chromium(2+) Chemical class [Cr+2] UZEDIBTVIIJELN-UHFFFAOYSA-N 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- MPTQRFCYZCXJFQ-UHFFFAOYSA-L copper(II) chloride dihydrate Chemical compound O.O.[Cl-].[Cl-].[Cu+2] MPTQRFCYZCXJFQ-UHFFFAOYSA-L 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- FNIATMYXUPOJRW-UHFFFAOYSA-N cyclohexylidene Chemical group [C]1CCCCC1 FNIATMYXUPOJRW-UHFFFAOYSA-N 0.000 description 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
- 238000006264 debenzylation reaction Methods 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
- TUEBAWASOGWJQN-UHFFFAOYSA-N diethyl 2,6-dimethyl-4-[4-(oxiran-2-ylmethoxy)phenyl]pyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C)N=C(C)C(C(=O)OCC)=C1C(C=C1)=CC=C1OCC1OC1 TUEBAWASOGWJQN-UHFFFAOYSA-N 0.000 description 1
- NRYUMDJGSZJVIC-UHFFFAOYSA-N diethyl 4-[4-[3-[2-(3-carbamoyl-4-hydroxyphenoxy)ethylamino]-2-hydroxypropoxy]phenyl]-2,6-dimethylpyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C)N=C(C)C(C(=O)OCC)=C1C(C=C1)=CC=C1OCC(O)CNCCOC1=CC=C(O)C(C(N)=O)=C1 NRYUMDJGSZJVIC-UHFFFAOYSA-N 0.000 description 1
- PGGQCHVPWSXPSI-UHFFFAOYSA-N diethyl pyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=CN=CC(C(=O)OCC)=C1 PGGQCHVPWSXPSI-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000003291 dopaminomimetic effect Effects 0.000 description 1
- 230000004406 elevated intraocular pressure Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 210000001105 femoral artery Anatomy 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 229960002598 fumaric acid Drugs 0.000 description 1
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 125000004970 halomethyl group Chemical group 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000003978 infusion fluid Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N iso-butene Natural products CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- DGEYTDCFMQMLTH-UHFFFAOYSA-N methanol;propan-2-ol Chemical compound OC.CC(C)O DGEYTDCFMQMLTH-UHFFFAOYSA-N 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- RMIODHQZRUFFFF-UHFFFAOYSA-N methoxyacetic acid Chemical compound COCC(O)=O RMIODHQZRUFFFF-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 1
- IDNSUFCVTLKERV-UHFFFAOYSA-N n'-methyl-4-phenylmethoxybenzenecarboximidamide Chemical compound C1=CC(C(=N)NC)=CC=C1OCC1=CC=CC=C1 IDNSUFCVTLKERV-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 229960003975 potassium Drugs 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 1
- 229960003147 reserpine Drugs 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 208000005057 thyrotoxicosis Diseases 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 210000001177 vas deferen Anatomy 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/333—Radicals substituted by oxygen or sulfur atoms
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- 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
- C07D239/26—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- C07D239/34—One oxygen atom
- C07D239/36—One oxygen atom as doubly bound oxygen atom or as unsubstituted hydroxy radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/24—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Steroid Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH365580 | 1980-05-09 |
Publications (1)
Publication Number | Publication Date |
---|---|
NO811568L true NO811568L (no) | 1981-11-10 |
Family
ID=4260677
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO811568A NO811568L (no) | 1980-05-09 | 1981-05-08 | Substituerte fenyletere. |
Country Status (17)
Country | Link |
---|---|
US (1) | US4559354A (da) |
EP (1) | EP0039892B1 (da) |
JP (1) | JPS5726653A (da) |
AT (1) | ATE24494T1 (da) |
AU (1) | AU542481B2 (da) |
DD (1) | DD158546A5 (da) |
DE (1) | DE3175753D1 (da) |
DK (1) | DK204681A (da) |
ES (5) | ES8206438A1 (da) |
FI (1) | FI811373L (da) |
GR (1) | GR75257B (da) |
HU (1) | HU192942B (da) |
IL (1) | IL62806A (da) |
NO (1) | NO811568L (da) |
NZ (1) | NZ197041A (da) |
PT (1) | PT73001B (da) |
ZA (1) | ZA813070B (da) |
Families Citing this family (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4574127A (en) * | 1984-05-07 | 1986-03-04 | Merck & Co., Inc. | Oxazoles and thiazoles containing an aminohydroxypropoxyphenyl moiety |
US4735961A (en) * | 1984-05-07 | 1988-04-05 | Merck & Co., Inc. | Oxazoles and thiazoles containing an aminohydroxypropoxyphenyl moiety |
IL82856A0 (en) * | 1986-06-26 | 1987-12-20 | Norwich Eaton Pharma | Pharmaceutical compositions containing 2-(5-phenyl-2-furanyl)imidazoles and certain such novel compounds |
US4895867A (en) * | 1986-06-26 | 1990-01-23 | Norwich Eaton Pharmaceuticals, Inc. | 2-(5-phenyl-2-furanyl)imidazoles useful as cardiotonic agents |
US5204463A (en) * | 1989-08-10 | 1993-04-20 | Glaxo Inc. | Substituted methoxyphenyl-4,5 dihydro-3(2H)-pridazinones having cardiotonic and beta blocking activities |
US5096904A (en) * | 1989-09-01 | 1992-03-17 | Glaxo Inc. | Pyridazinones having cardiotonic and beta blocking activities |
US5153209A (en) * | 1989-09-22 | 1992-10-06 | Glaxo Inc. | Pyridone nitriles useful in treating cardiovascular disease |
US5051431A (en) * | 1989-09-22 | 1991-09-24 | Glaxo Inc. | Pyridone nitriles useful in treating cardiovascular disease |
US5322845A (en) * | 1991-10-02 | 1994-06-21 | Sumitomo Chemical Company, Limited | Acrylic acid derivatives, a fungicide containing them as an active ingredient, and intermediate compounds thereof |
DE19500760A1 (de) * | 1995-01-13 | 1996-07-18 | Basf Ag | Substituierte 2-Phenylpyridine |
BR9910074A (pt) | 1998-04-29 | 2000-12-26 | Procter & Gamble | Processo para fabricação de uréias 1,3-di-substituìdas-4-oxocìclicas |
AU747237B2 (en) | 1998-04-29 | 2002-05-09 | Procter & Gamble Company, The | Process for making 1,3-disubstituted-4-oxocyclic ureas |
AU8430098A (en) * | 1998-07-23 | 2000-02-14 | Ing-Jun Chen | Guaiacoxypropanolamines with alpha/beta-adrenergic blocking activity |
US7998986B2 (en) | 2001-12-21 | 2011-08-16 | Exelixis Patent Company Llc | Modulators of LXR |
US7482366B2 (en) * | 2001-12-21 | 2009-01-27 | X-Ceptor Therapeutics, Inc. | Modulators of LXR |
JP2008534542A (ja) * | 2005-03-31 | 2008-08-28 | ユセベ ファルマ ソシエテ アノニム | オキサゾール部分又はチアゾール部分を含む化合物、それらの製造方法及びそれらの使用 |
EP1910307A1 (en) | 2005-06-27 | 2008-04-16 | Exelixis, Inc. | Pyrazole based lxr modulators |
DE102006052861A1 (de) | 2006-11-09 | 2008-05-15 | Zimmermann, Wolfgang, Prof. Dipl.-Ing. | Der Astromischer |
WO2011042475A1 (en) * | 2009-10-07 | 2011-04-14 | Karo Bio Ab | Substituted pyrazoles as estrogen receptor ligands |
GB201113538D0 (en) | 2011-08-04 | 2011-09-21 | Karobio Ab | Novel estrogen receptor ligands |
EP3522877B1 (en) | 2016-10-05 | 2023-12-06 | University of Pittsburgh - Of the Commonwealth System of Higher Education | Small molecule ampk activators |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4012444A (en) * | 1969-07-08 | 1977-03-15 | Allen & Hanburys Limited | 5-[1-Hydroxy-2-(1-methyl-3-phenylpropyl)aminoethyl] salicylamide and physiologically acceptable acid addition salts thereof |
GB1398738A (en) * | 1972-12-05 | 1975-06-25 | Pfizer Ltd | Propanolamine derivatives |
ZA754192B (en) * | 1974-08-05 | 1976-06-30 | Ciba Geigy Ag | 2-(aralkoxyphenyl)-1-(bis-arylalkylamino)-alkanes |
US4199580A (en) * | 1975-03-03 | 1980-04-22 | Merck & Co., Inc. | 3-Amino-2-or-propoxy-tetrahydronaphthyl or indanyl-substituted imidazoles and use |
US4134983A (en) * | 1975-03-03 | 1979-01-16 | Merck & Co., Inc. | 3-amino-2-or-propoxyaryl substituted imidazoles |
SE7601713L (sv) * | 1975-03-03 | 1976-09-06 | Merck & Co Inc | Nya, substituerad imidazoler |
FI791727A (fi) * | 1978-06-05 | 1979-12-06 | Ciba Geigy Ag | Foerfarande foer framstaellning av n-alkylerade aminoalkoholer |
DD150456A5 (de) * | 1979-03-01 | 1981-09-02 | Ciba Geigy Ag | Verfahren zur herstellung von derivaten des 3-amino-1,2-propandiols |
-
1981
- 1981-04-30 JP JP6435981A patent/JPS5726653A/ja active Pending
- 1981-05-04 FI FI811373A patent/FI811373L/fi not_active Application Discontinuation
- 1981-05-06 DE DE8181103418T patent/DE3175753D1/de not_active Expired
- 1981-05-06 EP EP81103418A patent/EP0039892B1/de not_active Expired
- 1981-05-06 AT AT81103418T patent/ATE24494T1/de not_active IP Right Cessation
- 1981-05-06 IL IL62806A patent/IL62806A/xx unknown
- 1981-05-07 ES ES501975A patent/ES8206438A1/es not_active Expired
- 1981-05-07 GR GR64877A patent/GR75257B/el unknown
- 1981-05-08 HU HU811245A patent/HU192942B/hu unknown
- 1981-05-08 PT PT73001A patent/PT73001B/pt unknown
- 1981-05-08 DK DK204681A patent/DK204681A/da not_active Application Discontinuation
- 1981-05-08 DD DD81229848A patent/DD158546A5/de unknown
- 1981-05-08 ZA ZA00813070A patent/ZA813070B/xx unknown
- 1981-05-08 AU AU70275/81A patent/AU542481B2/en not_active Ceased
- 1981-05-08 NO NO811568A patent/NO811568L/no unknown
- 1981-05-08 NZ NZ197041A patent/NZ197041A/en unknown
-
1982
- 1982-03-25 ES ES510816A patent/ES8305682A1/es not_active Expired
- 1982-03-25 ES ES510815A patent/ES8305681A1/es not_active Expired
- 1982-03-25 ES ES510813A patent/ES510813A0/es active Granted
- 1982-03-25 ES ES510814A patent/ES510814A0/es active Granted
-
1983
- 1983-05-06 US US06/490,211 patent/US4559354A/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
PT73001B (en) | 1983-02-08 |
PT73001A (en) | 1981-06-01 |
ES8305687A1 (es) | 1983-04-16 |
AU542481B2 (en) | 1985-02-21 |
HU192942B (en) | 1987-08-28 |
DD158546A5 (de) | 1983-01-19 |
IL62806A (en) | 1984-12-31 |
ES501975A0 (es) | 1982-08-16 |
ES510815A0 (es) | 1983-04-16 |
ES8305681A1 (es) | 1983-04-16 |
FI811373L (fi) | 1981-11-10 |
ES8305688A1 (es) | 1983-04-16 |
ZA813070B (en) | 1982-05-26 |
GR75257B (da) | 1984-07-13 |
AU7027581A (en) | 1981-11-12 |
US4559354A (en) | 1985-12-17 |
DK204681A (da) | 1981-11-10 |
JPS5726653A (en) | 1982-02-12 |
ATE24494T1 (de) | 1987-01-15 |
ES510816A0 (es) | 1983-04-16 |
EP0039892B1 (de) | 1986-12-30 |
ES8305682A1 (es) | 1983-04-16 |
ES510813A0 (es) | 1983-04-16 |
ES8206438A1 (es) | 1982-08-16 |
DE3175753D1 (en) | 1987-02-05 |
EP0039892A1 (de) | 1981-11-18 |
ES510814A0 (es) | 1983-04-16 |
NZ197041A (en) | 1984-02-03 |
IL62806A0 (en) | 1981-07-31 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
NO811568L (no) | Substituerte fenyletere. | |
US6911463B2 (en) | 3-substituted oxindole β-3 agonists | |
AU763040B2 (en) | Aromatic heterocycle compounds having HIV integrase inhibiting activities | |
CA1124241A (en) | N-alkylated aminoalcohols and their salts, processes for their preparation and pharmaceutical preparations containing these compounds | |
RU2284323C9 (ru) | Фенилэтенил- или фенилэтинилпроизводные в качестве антагонистов глутаматного рецептора | |
US4140789A (en) | Etherified hydroxy-benzodiheterocyclic compounds | |
EP1408950B1 (en) | Methods of treating cytokine mediated diseases | |
US7208505B2 (en) | β3 adrenergic agonists | |
NO167947B (no) | Lagringsanordning for baand- eller plate-registreringsmedier | |
JP2005501856A5 (da) | ||
JPH05503533A (ja) | 置換ベンジル要素を含むトリアゾールアンギオテンシン2拮抗物質 | |
EP0630374A1 (en) | Imidazole, triazole and tetrazole derivatives | |
NO811680L (no) | Fremgangsmaate for fremstilling av pyridoksin-derivater | |
NO834188L (no) | Fremgangsmaate til fremstilling av nye aryl-fenyleterderivater | |
CZ54095A3 (en) | Acetamides as such and for suppressing diseases, process of their preparation and their use for the preparation of medicaments, pharmaceutical preparations based thereon and process of their preparation | |
CA2312987A1 (en) | Selective .beta.3 adrenergic agonists | |
US5073563A (en) | Alkoxycoumarins substituted by a heterocyclic radical, their preparation and therapeutic agents containing these compounds | |
WO1993001177A1 (en) | Substituted triazolinones | |
US20060074084A1 (en) | Inhibitors of soluble adenylate cyclase | |
US20080004268A1 (en) | Inhibitors of soluble adenylate cyclase | |
CA1317948C (en) | Omega-¬(hetero)alkyl|benz¬cd|-indol-2-amines | |
NZ196365A (en) | 5-(omega-aminoalkyl(aryl or heteroaryl)alkylamino)-3-substituted-1h-1,2,4-triazoles | |
NO744530L (da) | ||
JPS59196879A (ja) | 新規な1,3,4−チアジアゾ−ル誘導体 | |
US5227392A (en) | Alkoxycoumarins substituted by a heterocyclic radical, their preparation and therapeutic agents containing these compounds |