NO309424B1 - Pyrimidindion-, pyrimidintrion-, triazindion-, tetrahydrokinazolindionderivater som <alfa>1-adrenergiske reseptorantagonister - Google Patents
Pyrimidindion-, pyrimidintrion-, triazindion-, tetrahydrokinazolindionderivater som <alfa>1-adrenergiske reseptorantagonister Download PDFInfo
- Publication number
- NO309424B1 NO309424B1 NO962412A NO962412A NO309424B1 NO 309424 B1 NO309424 B1 NO 309424B1 NO 962412 A NO962412 A NO 962412A NO 962412 A NO962412 A NO 962412A NO 309424 B1 NO309424 B1 NO 309424B1
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- pyrimidinedione
- phenyl
- formula
- trifluoroethoxy
- Prior art date
Links
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 title description 15
- 239000000674 adrenergic antagonist Substances 0.000 title description 2
- PKORYTIUMAOPED-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinazoline Chemical compound C1=CC=C2NCNCC2=C1 PKORYTIUMAOPED-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 287
- 229910052739 hydrogen Inorganic materials 0.000 claims description 98
- 239000001257 hydrogen Substances 0.000 claims description 98
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 95
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 93
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 93
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 72
- 125000000217 alkyl group Chemical group 0.000 claims description 61
- 150000002431 hydrogen Chemical class 0.000 claims description 59
- -1 hydroxyiminomethyl Chemical group 0.000 claims description 58
- 238000002360 preparation method Methods 0.000 claims description 50
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 44
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 35
- 150000003839 salts Chemical class 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 30
- 125000001072 heteroaryl group Chemical group 0.000 claims description 29
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 27
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 150000002367 halogens Chemical class 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- 239000011737 fluorine Substances 0.000 claims description 19
- 229910052731 fluorine Inorganic materials 0.000 claims description 19
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 16
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 16
- 150000001204 N-oxides Chemical class 0.000 claims description 15
- 201000010099 disease Diseases 0.000 claims description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
- 230000002152 alkylating effect Effects 0.000 claims description 13
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 12
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 125000002541 furyl group Chemical group 0.000 claims description 11
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 5
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 claims description 4
- ABFHOGGLXMLEPV-UHFFFAOYSA-N 2-[3-[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]propyl]-1,2,4-triazine-3,5-dione Chemical compound FC(F)(F)C1=CC=CC(N2CCN(CCCN3C(NC(=O)C=N3)=O)CC2)=C1 ABFHOGGLXMLEPV-UHFFFAOYSA-N 0.000 claims description 3
- NEQVOJLZTNUOMS-UHFFFAOYSA-N 3-[3-(4-phenylpiperazin-1-yl)propyl]-1,3-diazinane-2,4-dione;dihydrochloride Chemical compound Cl.Cl.O=C1CCNC(=O)N1CCCN1CCN(C=2C=CC=CC=2)CC1 NEQVOJLZTNUOMS-UHFFFAOYSA-N 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
- 239000005977 Ethylene Substances 0.000 claims description 3
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 3
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 claims description 3
- 210000001635 urinary tract Anatomy 0.000 claims description 3
- RCOBWVAGWYRNHZ-UHFFFAOYSA-N 5-methyl-3-[3-[4-[2-(2,2,2-trifluoroethoxy)phenyl]-1-piperazinyl]propyl]-1H-pyrimidine-2,4-dione Chemical compound O=C1C(C)=CNC(=O)N1CCCN1CCN(C=2C(=CC=CC=2)OCC(F)(F)F)CC1 RCOBWVAGWYRNHZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 239000000203 mixture Substances 0.000 description 183
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 168
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 156
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 147
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 144
- 239000000243 solution Substances 0.000 description 117
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 114
- 229910001868 water Inorganic materials 0.000 description 91
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 82
- 239000002904 solvent Substances 0.000 description 76
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 75
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 74
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 65
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 56
- 238000001953 recrystallisation Methods 0.000 description 55
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 54
- 238000010992 reflux Methods 0.000 description 50
- 239000001530 fumaric acid Substances 0.000 description 48
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 46
- 125000003821 2-(trimethylsilyl)ethoxymethyl group Chemical group [H]C([H])([H])[Si](C([H])([H])[H])(C([H])([H])[H])C([H])([H])C(OC([H])([H])[*])([H])[H] 0.000 description 42
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 42
- 238000006243 chemical reaction Methods 0.000 description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
- 239000002585 base Substances 0.000 description 40
- STALANBIHAODET-UHFFFAOYSA-N 1-[2-(2,2,2-trifluoroethoxy)phenyl]piperazine Chemical compound FC(F)(F)COC1=CC=CC=C1N1CCNCC1 STALANBIHAODET-UHFFFAOYSA-N 0.000 description 39
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
- 239000011541 reaction mixture Substances 0.000 description 39
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 38
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 37
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 33
- 239000000741 silica gel Substances 0.000 description 33
- 229910002027 silica gel Inorganic materials 0.000 description 33
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 30
- 238000012360 testing method Methods 0.000 description 29
- 210000001519 tissue Anatomy 0.000 description 29
- 239000000284 extract Substances 0.000 description 26
- 210000003932 urinary bladder Anatomy 0.000 description 25
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000002253 acid Substances 0.000 description 24
- 239000003960 organic solvent Substances 0.000 description 23
- 229910000027 potassium carbonate Inorganic materials 0.000 description 23
- 235000011181 potassium carbonates Nutrition 0.000 description 23
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 22
- 125000006239 protecting group Chemical group 0.000 description 22
- 239000007787 solid Substances 0.000 description 22
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
- 239000003921 oil Substances 0.000 description 19
- 235000019198 oils Nutrition 0.000 description 19
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 18
- 239000012267 brine Substances 0.000 description 18
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 18
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 18
- 239000007858 starting material Substances 0.000 description 17
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 16
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 16
- 229960002748 norepinephrine Drugs 0.000 description 16
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 16
- 150000003254 radicals Chemical class 0.000 description 16
- 210000002460 smooth muscle Anatomy 0.000 description 16
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 15
- 238000004440 column chromatography Methods 0.000 description 15
- 230000008602 contraction Effects 0.000 description 15
- 239000012312 sodium hydride Substances 0.000 description 15
- 229910000104 sodium hydride Inorganic materials 0.000 description 15
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 15
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 14
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- 150000001298 alcohols Chemical class 0.000 description 13
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 13
- 239000012458 free base Substances 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 12
- BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 241000700159 Rattus Species 0.000 description 12
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
- 239000012298 atmosphere Substances 0.000 description 12
- 230000036772 blood pressure Effects 0.000 description 12
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 12
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 12
- 230000001404 mediated effect Effects 0.000 description 12
- WBXQIAKHNGXXCJ-UHFFFAOYSA-N 1-(4-fluoro-2-methoxyphenyl)piperazine Chemical compound COC1=CC(F)=CC=C1N1CCNCC1 WBXQIAKHNGXXCJ-UHFFFAOYSA-N 0.000 description 11
- ZADZZEZAWMZYEC-UHFFFAOYSA-N 1-[4-fluoro-2-(2,2,2-trifluoroethoxy)phenyl]piperazine Chemical compound FC(F)(F)COC1=CC(F)=CC=C1N1CCNCC1 ZADZZEZAWMZYEC-UHFFFAOYSA-N 0.000 description 11
- 229910052786 argon Inorganic materials 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- 239000000725 suspension Substances 0.000 description 11
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 10
- SONNWYBIRXJNDC-VIFPVBQESA-N phenylephrine Chemical compound CNC[C@H](O)C1=CC=CC(O)=C1 SONNWYBIRXJNDC-VIFPVBQESA-N 0.000 description 10
- 229960001802 phenylephrine Drugs 0.000 description 10
- 230000004044 response Effects 0.000 description 10
- 230000000284 resting effect Effects 0.000 description 10
- RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 description 10
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 10
- 238000001727 in vivo Methods 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- 239000002168 alkylating agent Substances 0.000 description 8
- 229940100198 alkylating agent Drugs 0.000 description 8
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(i) oxide Chemical compound [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 8
- 239000006260 foam Substances 0.000 description 8
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 210000002307 prostate Anatomy 0.000 description 8
- 230000009467 reduction Effects 0.000 description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 7
- 230000029936 alkylation Effects 0.000 description 7
- 238000005804 alkylation reaction Methods 0.000 description 7
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 7
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 7
- 229910000024 caesium carbonate Inorganic materials 0.000 description 7
- 238000004587 chromatography analysis Methods 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 239000012279 sodium borohydride Substances 0.000 description 7
- 229910000033 sodium borohydride Inorganic materials 0.000 description 7
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 7
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 6
- YSEWXFSLNGJJAO-UHFFFAOYSA-N 1-(4-chloro-2-methoxyphenyl)piperazine Chemical compound COC1=CC(Cl)=CC=C1N1CCNCC1 YSEWXFSLNGJJAO-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 241000282412 Homo Species 0.000 description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 6
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
- 241000283973 Oryctolagus cuniculus Species 0.000 description 6
- 239000004698 Polyethylene Substances 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 239000000443 aerosol Substances 0.000 description 6
- 239000000908 ammonium hydroxide Substances 0.000 description 6
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 6
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 6
- 239000003638 chemical reducing agent Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 6
- PPXUHEORWJQRHJ-UHFFFAOYSA-N ethyl isovalerate Chemical compound CCOC(=O)CC(C)C PPXUHEORWJQRHJ-UHFFFAOYSA-N 0.000 description 6
- 238000003818 flash chromatography Methods 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 6
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
- 229920000573 polyethylene Polymers 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- 235000009518 sodium iodide Nutrition 0.000 description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N 1-propanol Substances CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 5
- WWXFHHXOVMQARV-UHFFFAOYSA-N 3-hydroxy-2,2-dimethylpropanenitrile Chemical compound OCC(C)(C)C#N WWXFHHXOVMQARV-UHFFFAOYSA-N 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- 102000015005 beta-adrenergic receptor activity proteins Human genes 0.000 description 5
- 108040006818 beta-adrenergic receptor activity proteins Proteins 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 238000000338 in vitro Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 238000011835 investigation Methods 0.000 description 5
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 5
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 5
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 5
- 238000012544 monitoring process Methods 0.000 description 5
- 235000006408 oxalic acid Nutrition 0.000 description 5
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 5
- IENZQIKPVFGBNW-UHFFFAOYSA-N prazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 IENZQIKPVFGBNW-UHFFFAOYSA-N 0.000 description 5
- 229960001289 prazosin Drugs 0.000 description 5
- 235000019260 propionic acid Nutrition 0.000 description 5
- 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 5
- 230000000638 stimulation Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- QCIKJNCYPRDVQN-UHFFFAOYSA-N (1-cyanocyclopropyl)methyl methanesulfonate Chemical compound CS(=O)(=O)OCC1(C#N)CC1 QCIKJNCYPRDVQN-UHFFFAOYSA-N 0.000 description 4
- AYNDDGCBWJPGSG-UHFFFAOYSA-N 1-[4-chloro-2-(2,2,2-trifluoroethoxy)phenyl]piperazine Chemical compound FC(F)(F)COC1=CC(Cl)=CC=C1N1CCNCC1 AYNDDGCBWJPGSG-UHFFFAOYSA-N 0.000 description 4
- KGNQDBQYEBMPFZ-UHFFFAOYSA-N 1-fluoro-4-iodobenzene Chemical compound FC1=CC=C(I)C=C1 KGNQDBQYEBMPFZ-UHFFFAOYSA-N 0.000 description 4
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 4
- JIKIVGTUYSNUPQ-UHFFFAOYSA-N 2-(2,2,2-trifluoroethoxy)aniline Chemical compound NC1=CC=CC=C1OCC(F)(F)F JIKIVGTUYSNUPQ-UHFFFAOYSA-N 0.000 description 4
- DFBWEIMTNJWBCJ-UHFFFAOYSA-N 2-(2-fluorophenyl)-1,3-oxazole Chemical compound FC1=CC=CC=C1C1=NC=CO1 DFBWEIMTNJWBCJ-UHFFFAOYSA-N 0.000 description 4
- BPXKZEMBEZGUAH-UHFFFAOYSA-N 2-(chloromethoxy)ethyl-trimethylsilane Chemical compound C[Si](C)(C)CCOCCl BPXKZEMBEZGUAH-UHFFFAOYSA-N 0.000 description 4
- YMDZDFSUDFLGMX-UHFFFAOYSA-N 2-chloro-n-(2-chloroethyl)ethanamine;hydron;chloride Chemical compound [Cl-].ClCC[NH2+]CCCl YMDZDFSUDFLGMX-UHFFFAOYSA-N 0.000 description 4
- FOXQGUQJESLPCG-UHFFFAOYSA-N 4-(2-aminophenyl)piperazine-1-carbaldehyde Chemical compound NC1=CC=CC=C1N1CCN(C=O)CC1 FOXQGUQJESLPCG-UHFFFAOYSA-N 0.000 description 4
- IMGYXLLIYDTNST-UHFFFAOYSA-N 4-(2-nitrophenyl)piperazine-1-carbaldehyde Chemical compound [O-][N+](=O)C1=CC=CC=C1N1CCN(C=O)CC1 IMGYXLLIYDTNST-UHFFFAOYSA-N 0.000 description 4
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- 241000282472 Canis lupus familiaris Species 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 4
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 4
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 4
- 239000000556 agonist Substances 0.000 description 4
- 239000005557 antagonist Substances 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- UUWSLBWDFJMSFP-UHFFFAOYSA-N bromomethylcyclohexane Chemical compound BrCC1CCCCC1 UUWSLBWDFJMSFP-UHFFFAOYSA-N 0.000 description 4
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 4
- 230000001186 cumulative effect Effects 0.000 description 4
- 239000008121 dextrose Substances 0.000 description 4
- 230000002140 halogenating effect Effects 0.000 description 4
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 4
- 238000007915 intraurethral administration Methods 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 4
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 4
- 235000019796 monopotassium phosphate Nutrition 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000012746 preparative thin layer chromatography Methods 0.000 description 4
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 4
- 229940113082 thymine Drugs 0.000 description 4
- 229940035893 uracil Drugs 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- SAXORHBYDHQFHF-UHFFFAOYSA-N 1-(2-pyrrol-1-ylphenyl)piperazine Chemical compound C1CNCCN1C1=CC=CC=C1N1C=CC=C1 SAXORHBYDHQFHF-UHFFFAOYSA-N 0.000 description 3
- TXIDGXPOQRNGLA-UHFFFAOYSA-N 1-(4-fluorophenyl)-5-methylpyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(C)=CN1C1=CC=C(F)C=C1 TXIDGXPOQRNGLA-UHFFFAOYSA-N 0.000 description 3
- SEXZHJJUKFXNDY-UHFFFAOYSA-N 1-(bromomethyl)-2-phenylbenzene Chemical compound BrCC1=CC=CC=C1C1=CC=CC=C1 SEXZHJJUKFXNDY-UHFFFAOYSA-N 0.000 description 3
- WZRKSPFYXUXINF-UHFFFAOYSA-N 1-(bromomethyl)-4-methylbenzene Chemical compound CC1=CC=C(CBr)C=C1 WZRKSPFYXUXINF-UHFFFAOYSA-N 0.000 description 3
- MCECCMHXOWBRAA-UHFFFAOYSA-N 1-benzyl-3-(3-chloropropyl)-5,5-dimethyl-1,3-diazinane-2,4,6-trione Chemical compound O=C1C(C)(C)C(=O)N(CCCCl)C(=O)N1CC1=CC=CC=C1 MCECCMHXOWBRAA-UHFFFAOYSA-N 0.000 description 3
- YNHQGNHVHHZPTA-UHFFFAOYSA-N 1-benzyl-5-methylpyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(C)=CN1CC1=CC=CC=C1 YNHQGNHVHHZPTA-UHFFFAOYSA-N 0.000 description 3
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 3
- WGNQXOOZRSACBQ-UHFFFAOYSA-N 2-(2-fluorophenyl)-4,5-dihydro-1,3-oxazole Chemical compound FC1=CC=CC=C1C1=NCCO1 WGNQXOOZRSACBQ-UHFFFAOYSA-N 0.000 description 3
- GIGLAIRYCCEWSZ-UHFFFAOYSA-N 2-(2-piperazin-1-ylphenyl)-1,3-oxazole Chemical compound C1CNCCN1C1=CC=CC=C1C1=NC=CO1 GIGLAIRYCCEWSZ-UHFFFAOYSA-N 0.000 description 3
- VNMORBLLLTZLLT-UHFFFAOYSA-N 2-(bromomethyl)pyrazine Chemical compound BrCC1=CN=CC=N1 VNMORBLLLTZLLT-UHFFFAOYSA-N 0.000 description 3
- DZDVNAVPCCNJRK-UHFFFAOYSA-N 2-cyano-2-methylpropanoic acid Chemical compound N#CC(C)(C)C(O)=O DZDVNAVPCCNJRK-UHFFFAOYSA-N 0.000 description 3
- CPKISUMKCULUNR-UHFFFAOYSA-N 2-methoxy-2-oxoacetic acid Chemical compound COC(=O)C(O)=O CPKISUMKCULUNR-UHFFFAOYSA-N 0.000 description 3
- LYIAUQYGZRRMRN-UHFFFAOYSA-N 3-(3-chloropropyl)-6-methyl-1h-pyrimidine-2,4-dione Chemical compound CC1=CC(=O)N(CCCCl)C(=O)N1 LYIAUQYGZRRMRN-UHFFFAOYSA-N 0.000 description 3
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
- DRLMXVMLMGPVRC-UHFFFAOYSA-N 5,6,7,8-tetrahydro-1h-quinazoline-2,4-dione Chemical class C1CCCC2=C1NC(=O)NC2=O DRLMXVMLMGPVRC-UHFFFAOYSA-N 0.000 description 3
- OHAMXGZMZZWRCA-UHFFFAOYSA-N 5-formyluracil Chemical class OC1=NC=C(C=O)C(O)=N1 OHAMXGZMZZWRCA-UHFFFAOYSA-N 0.000 description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 206010031127 Orthostatic hypotension Diseases 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
- 239000011260 aqueous acid Substances 0.000 description 3
- FKPSBYZGRQJIMO-UHFFFAOYSA-M benzyl(triethyl)azanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC1=CC=CC=C1 FKPSBYZGRQJIMO-UHFFFAOYSA-M 0.000 description 3
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 3
- 230000004531 blood pressure lowering effect Effects 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 150000007942 carboxylates Chemical class 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 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
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 238000006264 debenzylation reaction Methods 0.000 description 3
- 230000017858 demethylation Effects 0.000 description 3
- 238000010520 demethylation reaction Methods 0.000 description 3
- 230000001419 dependent effect Effects 0.000 description 3
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 3
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 3
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N dimethylmethane Natural products CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 3
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 3
- 210000001105 femoral artery Anatomy 0.000 description 3
- 210000003191 femoral vein Anatomy 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 3
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- FDEQIQCNKZPJQR-UHFFFAOYSA-N hydrogen peroxide;nickel;hydrate Chemical compound O.[Ni].OO FDEQIQCNKZPJQR-UHFFFAOYSA-N 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 230000003301 hydrolyzing effect Effects 0.000 description 3
- 150000007529 inorganic bases Chemical class 0.000 description 3
- 238000012423 maintenance Methods 0.000 description 3
- 125000005948 methanesulfonyloxy group Chemical group 0.000 description 3
- MDEDOIDXVJXDBW-UHFFFAOYSA-N methoxymethyl acetate Chemical compound COCOC(C)=O MDEDOIDXVJXDBW-UHFFFAOYSA-N 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- 210000003205 muscle Anatomy 0.000 description 3
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 231100000252 nontoxic Toxicity 0.000 description 3
- 230000003000 nontoxic effect Effects 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 3
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 3
- 229910000105 potassium hydride Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 230000011514 reflex Effects 0.000 description 3
- 238000011699 spontaneously hypertensive rat Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 2
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
- DZKRDHLYQRTDBU-UPHRSURJSA-N (z)-but-2-enediperoxoic acid Chemical compound OOC(=O)\C=C/C(=O)OO DZKRDHLYQRTDBU-UPHRSURJSA-N 0.000 description 2
- HGJFLOVNAPLBKM-UHFFFAOYSA-N 1-(2-ethoxy-4-fluorophenyl)piperazine Chemical compound CCOC1=CC(F)=CC=C1N1CCNCC1 HGJFLOVNAPLBKM-UHFFFAOYSA-N 0.000 description 2
- VNZLQLYBRIOLFZ-UHFFFAOYSA-N 1-(2-methoxyphenyl)piperazine Chemical compound COC1=CC=CC=C1N1CCNCC1 VNZLQLYBRIOLFZ-UHFFFAOYSA-N 0.000 description 2
- UHNRTFSKVNOUGK-UHFFFAOYSA-N 1-(2-trimethylsilylethoxymethyl)pyrimidine-2,4-dione Chemical compound C[Si](C)(C)CCOCN1C=CC(=O)NC1=O UHNRTFSKVNOUGK-UHFFFAOYSA-N 0.000 description 2
- GYYNRYYAJBOYDK-UHFFFAOYSA-N 1-(3-bromopropyl)-4-(2-methoxyphenyl)piperazine Chemical compound COC1=CC=CC=C1N1CCN(CCCBr)CC1 GYYNRYYAJBOYDK-UHFFFAOYSA-N 0.000 description 2
- FPGCIEJQYIPOEI-UHFFFAOYSA-N 1-(3-bromopropyl)-4-[2-(2,2,2-trifluoroethoxy)phenyl]piperazine Chemical compound FC(F)(F)COC1=CC=CC=C1N1CCN(CCCBr)CC1 FPGCIEJQYIPOEI-UHFFFAOYSA-N 0.000 description 2
- HQZHKJREQHUIPT-UHFFFAOYSA-N 1-(3-chloropropyl)-3-(4-fluorophenyl)-5-methylpyrimidine-2,4-dione Chemical compound O=C1C(C)=CN(CCCCl)C(=O)N1C1=CC=C(F)C=C1 HQZHKJREQHUIPT-UHFFFAOYSA-N 0.000 description 2
- IWOWNAOOWXAEIQ-UHFFFAOYSA-N 1-(3-chloropropyl)-5-methyl-3-phenylpyrimidine-2,4-dione Chemical compound O=C1C(C)=CN(CCCCl)C(=O)N1C1=CC=CC=C1 IWOWNAOOWXAEIQ-UHFFFAOYSA-N 0.000 description 2
- LYPKLJIYXQVTPF-UHFFFAOYSA-N 1-(5-fluoro-2-methoxyphenyl)piperazine Chemical compound COC1=CC=C(F)C=C1N1CCNCC1 LYPKLJIYXQVTPF-UHFFFAOYSA-N 0.000 description 2
- BAARUIIACXPYNI-UHFFFAOYSA-N 1-(cyclohexylmethyl)-5-methylpyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(C)=CN1CC1CCCCC1 BAARUIIACXPYNI-UHFFFAOYSA-N 0.000 description 2
- MSSDTZLYNMFTKN-UHFFFAOYSA-N 1-Piperazinecarboxaldehyde Chemical compound O=CN1CCNCC1 MSSDTZLYNMFTKN-UHFFFAOYSA-N 0.000 description 2
- NONHMRZXKRBXRX-UHFFFAOYSA-N 1-[2-(trifluoromethoxy)phenyl]piperazine Chemical compound FC(F)(F)OC1=CC=CC=C1N1CCNCC1 NONHMRZXKRBXRX-UHFFFAOYSA-N 0.000 description 2
- HKOXZKWRHOVZHC-UHFFFAOYSA-N 1-[4-methoxy-2-(2,2,2-trifluoroethoxy)phenyl]piperazine Chemical compound FC(F)(F)COC1=CC(OC)=CC=C1N1CCNCC1 HKOXZKWRHOVZHC-UHFFFAOYSA-N 0.000 description 2
- KSGIAVUJLKAGPF-UHFFFAOYSA-N 1-[4-methyl-2-(2,2,2-trifluoroethoxy)phenyl]piperazine Chemical compound FC(F)(F)COC1=CC(C)=CC=C1N1CCNCC1 KSGIAVUJLKAGPF-UHFFFAOYSA-N 0.000 description 2
- ZEOXEPOHKHVSJR-UHFFFAOYSA-N 1-benzyl-2,4-dioxopyrimidine-5-carbaldehyde Chemical compound O=C1NC(=O)C(C=O)=CN1CC1=CC=CC=C1 ZEOXEPOHKHVSJR-UHFFFAOYSA-N 0.000 description 2
- QHQXHAXVJFKZCI-UHFFFAOYSA-N 1-benzyl-3-(3-chloropropyl)-5-methylpyrimidine-2,4-dione Chemical compound O=C1N(CCCCl)C(=O)C(C)=CN1CC1=CC=CC=C1 QHQXHAXVJFKZCI-UHFFFAOYSA-N 0.000 description 2
- JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 2
- DLJUDLUVULSXDS-UHFFFAOYSA-N 1-nitro-2-(2,2,2-trifluoroethoxy)benzene Chemical compound [O-][N+](=O)C1=CC=CC=C1OCC(F)(F)F DLJUDLUVULSXDS-UHFFFAOYSA-N 0.000 description 2
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 2
- XYPISWUKQGWYGX-UHFFFAOYSA-N 2,2,2-trifluoroethaneperoxoic acid Chemical compound OOC(=O)C(F)(F)F XYPISWUKQGWYGX-UHFFFAOYSA-N 0.000 description 2
- IGKCQDUYZULGBM-UHFFFAOYSA-N 2,2,2-trifluoroethyl 4-methylbenzenesulfonate Chemical compound CC1=CC=C(S(=O)(=O)OCC(F)(F)F)C=C1 IGKCQDUYZULGBM-UHFFFAOYSA-N 0.000 description 2
- QSKUPSCDXGKLKA-UHFFFAOYSA-N 2,2-dimethyl-3-phenylmethoxy-1-[4-[2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl]propan-1-one Chemical compound C1CN(C=2C(=CC=CC=2)OCC(F)(F)F)CCN1C(=O)C(C)(C)COCC1=CC=CC=C1 QSKUPSCDXGKLKA-UHFFFAOYSA-N 0.000 description 2
- QOEZRCXOHOVLBF-UHFFFAOYSA-N 2,2-dimethyl-3-phenylmethoxypropanenitrile Chemical compound N#CC(C)(C)COCC1=CC=CC=C1 QOEZRCXOHOVLBF-UHFFFAOYSA-N 0.000 description 2
- GPWNWKWQOLEVEQ-UHFFFAOYSA-N 2,4-diaminopyrimidine-5-carbaldehyde Chemical compound NC1=NC=C(C=O)C(N)=N1 GPWNWKWQOLEVEQ-UHFFFAOYSA-N 0.000 description 2
- GFISDBXSWQMOND-UHFFFAOYSA-N 2,5-dimethoxyoxolane Chemical compound COC1CCC(OC)O1 GFISDBXSWQMOND-UHFFFAOYSA-N 0.000 description 2
- QNBUDXGIGSTILK-UHFFFAOYSA-N 2-(5-fluoro-2-piperazin-1-ylphenyl)-1,3-oxazole Chemical compound N=1C=COC=1C1=CC(F)=CC=C1N1CCNCC1 QNBUDXGIGSTILK-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- WJBOILWAAHSGMY-UHFFFAOYSA-N 2-[2-(4-benzylpiperazin-1-yl)phenyl]-1,3-oxazole Chemical compound C=1C=CC=CC=1CN(CC1)CCN1C1=CC=CC=C1C1=NC=CO1 WJBOILWAAHSGMY-UHFFFAOYSA-N 0.000 description 2
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 2
- XNINAOUGJUYOQX-UHFFFAOYSA-N 2-cyanobutanoic acid Chemical compound CCC(C#N)C(O)=O XNINAOUGJUYOQX-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- 229940093475 2-ethoxyethanol Drugs 0.000 description 2
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 2
- ICPWFHKNYYRBSZ-UHFFFAOYSA-M 2-methoxypropanoate Chemical compound COC(C)C([O-])=O ICPWFHKNYYRBSZ-UHFFFAOYSA-M 0.000 description 2
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 2
- WXNVAIJRKJUOHQ-UHFFFAOYSA-N 3-(3-chloropropyl)-1-(2-trimethylsilylethoxymethyl)pyrimidine-2,4-dione Chemical compound C[Si](C)(C)CCOCN1C=CC(=O)N(CCCCl)C1=O WXNVAIJRKJUOHQ-UHFFFAOYSA-N 0.000 description 2
- FRFYTPKVNGOKBH-UHFFFAOYSA-N 3-(3-chloropropyl)-5-methyl-1-(pyridin-4-ylmethyl)pyrimidine-2,4-dione Chemical compound O=C1N(CCCCl)C(=O)C(C)=CN1CC1=CC=NC=C1 FRFYTPKVNGOKBH-UHFFFAOYSA-N 0.000 description 2
- PAVTXRUVHZTXBA-UHFFFAOYSA-N 3-(3-chloropropyl)-5-methyl-1h-pyrimidine-2,4-dione Chemical compound CC1=CNC(=O)N(CCCCl)C1=O PAVTXRUVHZTXBA-UHFFFAOYSA-N 0.000 description 2
- XZSMMBREXACMOX-UHFFFAOYSA-N 3-(4-fluorophenyl)-5-methyl-1h-pyrimidine-2,4-dione Chemical compound O=C1C(C)=CNC(=O)N1C1=CC=C(F)C=C1 XZSMMBREXACMOX-UHFFFAOYSA-N 0.000 description 2
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 2
- OCAXNVFTQRWAPL-UHFFFAOYSA-N 3-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-5-methyl-1h-pyrimidine-2,4-dione Chemical compound COC1=CC=CC=C1N1CCN(CCCN2C(C(C)=CNC2=O)=O)CC1 OCAXNVFTQRWAPL-UHFFFAOYSA-N 0.000 description 2
- OAKURXIZZOAYBC-UHFFFAOYSA-N 3-oxopropanoic acid Chemical compound OC(=O)CC=O OAKURXIZZOAYBC-UHFFFAOYSA-N 0.000 description 2
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 2
- TZYICBPLJDPGPB-UHFFFAOYSA-N 4-(2-pyrrol-1-ylphenyl)piperazine-1-carbaldehyde Chemical compound C1CN(C=O)CCN1C1=CC=CC=C1N1C=CC=C1 TZYICBPLJDPGPB-UHFFFAOYSA-N 0.000 description 2
- WZIYCIBURCPKAR-UHFFFAOYSA-N 4-(chloromethyl)pyridine Chemical compound ClCC1=CC=NC=C1 WZIYCIBURCPKAR-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- USOVRXNIZFSGEU-UHFFFAOYSA-N 4-fluoro-1-nitro-2-(2,2,2-trifluoroethoxy)benzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1OCC(F)(F)F USOVRXNIZFSGEU-UHFFFAOYSA-N 0.000 description 2
- KTJBWMIVXDHCNT-UHFFFAOYSA-N 4-fluoro-2-(2,2,2-trifluoroethoxy)aniline Chemical compound NC1=CC=C(F)C=C1OCC(F)(F)F KTJBWMIVXDHCNT-UHFFFAOYSA-N 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- ZVWXSZQQSVVBEW-UHFFFAOYSA-N 4-piperazin-1-yl-3-(2,2,2-trifluoroethoxy)phenol Chemical compound FC(F)(F)COC1=CC(O)=CC=C1N1CCNCC1 ZVWXSZQQSVVBEW-UHFFFAOYSA-N 0.000 description 2
- OIVLITBTBDPEFK-UHFFFAOYSA-N 5,6-dihydrouracil Chemical compound O=C1CCNC(=O)N1 OIVLITBTBDPEFK-UHFFFAOYSA-N 0.000 description 2
- DURJNFNACYMBQG-UHFFFAOYSA-N 5-(dimethylamino)-3-[3-[4-[4-fluoro-2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl]propyl]-1-(2-trimethylsilylethoxymethyl)pyrimidine-2,4-dione Chemical compound O=C1C(N(C)C)=CN(COCC[Si](C)(C)C)C(=O)N1CCCN1CCN(C=2C(=CC(F)=CC=2)OCC(F)(F)F)CC1 DURJNFNACYMBQG-UHFFFAOYSA-N 0.000 description 2
- VBGVWIZIDMFPKA-UHFFFAOYSA-N 5-(hydroxyiminomethyl)-1H-pyrimidine-2,4-dione Chemical compound ON=CC1=CNC(=O)NC1=O VBGVWIZIDMFPKA-UHFFFAOYSA-N 0.000 description 2
- JDBGXEHEIRGOBU-UHFFFAOYSA-N 5-hydroxymethyluracil Chemical compound OCC1=CNC(=O)NC1=O JDBGXEHEIRGOBU-UHFFFAOYSA-N 0.000 description 2
- KELXHQACBIUYSE-UHFFFAOYSA-N 5-methoxy-1h-pyrimidine-2,4-dione Chemical compound COC1=CNC(=O)NC1=O KELXHQACBIUYSE-UHFFFAOYSA-N 0.000 description 2
- NWNKIJNFNJCAHN-UHFFFAOYSA-N 5-propan-2-yl-1h-pyrimidine-2,4-dione Chemical compound CC(C)C1=CNC(=O)NC1=O NWNKIJNFNJCAHN-UHFFFAOYSA-N 0.000 description 2
- 108060003345 Adrenergic Receptor Proteins 0.000 description 2
- 102000017910 Adrenergic receptor Human genes 0.000 description 2
- 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 2
- 240000002470 Amphicarpaea bracteata Species 0.000 description 2
- 206010002091 Anaesthesia Diseases 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- KCMZYCFSSYXEQR-UHFFFAOYSA-N CCCC[K] Chemical compound CCCC[K] KCMZYCFSSYXEQR-UHFFFAOYSA-N 0.000 description 2
- IRDQNLLVRXMERV-UHFFFAOYSA-N CCCC[Na] Chemical compound CCCC[Na] IRDQNLLVRXMERV-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 2
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 2
- OMFXVFTZEKFJBZ-UHFFFAOYSA-N Corticosterone Natural products O=C1CCC2(C)C3C(O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 OMFXVFTZEKFJBZ-UHFFFAOYSA-N 0.000 description 2
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 239000007836 KH2PO4 Substances 0.000 description 2
- 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 2
- 239000012448 Lithium borohydride Substances 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 2
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical class [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 2
- NFMCQNMBFLPELK-UHFFFAOYSA-N OCCC1(CC1)C#N Chemical compound OCCC1(CC1)C#N NFMCQNMBFLPELK-UHFFFAOYSA-N 0.000 description 2
- 208000036576 Obstructive uropathy Diseases 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- 235000019483 Peanut oil Nutrition 0.000 description 2
- QGMRQYFBGABWDR-UHFFFAOYSA-M Pentobarbital sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)[N-]C1=O QGMRQYFBGABWDR-UHFFFAOYSA-M 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical 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
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 235000011941 Tilia x europaea Nutrition 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 229910052783 alkali metal Inorganic materials 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
- 230000037005 anaesthesia Effects 0.000 description 2
- 239000010775 animal oil Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 230000004872 arterial blood pressure Effects 0.000 description 2
- 210000001367 artery Anatomy 0.000 description 2
- 235000010323 ascorbic acid Nutrition 0.000 description 2
- 229960005070 ascorbic acid Drugs 0.000 description 2
- 239000011668 ascorbic acid Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- RJNJWHFSKNJCTB-UHFFFAOYSA-N benzylurea Chemical compound NC(=O)NCC1=CC=CC=C1 RJNJWHFSKNJCTB-UHFFFAOYSA-N 0.000 description 2
- 239000002876 beta blocker Substances 0.000 description 2
- 210000005068 bladder tissue Anatomy 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- QDWJUBJKEHXSMT-UHFFFAOYSA-N boranylidynenickel Chemical compound [Ni]#B QDWJUBJKEHXSMT-UHFFFAOYSA-N 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 235000011148 calcium chloride Nutrition 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 150000005323 carbonate salts Chemical class 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 2
- 229960003920 cocaine Drugs 0.000 description 2
- 230000009989 contractile response Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 2
- OMFXVFTZEKFJBZ-HJTSIMOOSA-N corticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OMFXVFTZEKFJBZ-HJTSIMOOSA-N 0.000 description 2
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 230000001335 demethylating effect Effects 0.000 description 2
- 238000010494 dissociation reaction Methods 0.000 description 2
- 230000005593 dissociations Effects 0.000 description 2
- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 150000002168 ethanoic acid esters Chemical class 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 2
- SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 229940093915 gynecological organic acid Drugs 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229960000905 indomethacin Drugs 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 2
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 239000004571 lime Substances 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000001630 malic acid Substances 0.000 description 2
- 235000011090 malic acid Nutrition 0.000 description 2
- 229960002510 mandelic acid Drugs 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- TXXHDPDFNKHHGW-UHFFFAOYSA-N muconic acid Chemical compound OC(=O)C=CC=CC(O)=O TXXHDPDFNKHHGW-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 230000007383 nerve stimulation Effects 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 229920002866 paraformaldehyde Polymers 0.000 description 2
- 239000000312 peanut oil Substances 0.000 description 2
- 229960002275 pentobarbital sodium Drugs 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229940124531 pharmaceutical excipient Drugs 0.000 description 2
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical group CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- 235000011056 potassium acetate Nutrition 0.000 description 2
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 229960003712 propranolol Drugs 0.000 description 2
- 239000003223 protective agent Substances 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 238000002390 rotary evaporation Methods 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000008159 sesame oil Substances 0.000 description 2
- 235000011803 sesame oil Nutrition 0.000 description 2
- 235000020183 skimmed milk Nutrition 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 2
- 239000012439 solid excipient Substances 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 238000013268 sustained release Methods 0.000 description 2
- 239000012730 sustained-release form Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 2
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 2
- RXMRGBVLCSYIBO-UHFFFAOYSA-M tetramethylazanium;iodide Chemical compound [I-].C[N+](C)(C)C RXMRGBVLCSYIBO-UHFFFAOYSA-M 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical group CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 210000003708 urethra Anatomy 0.000 description 2
- 230000036325 urinary excretion Effects 0.000 description 2
- 201000002327 urinary tract obstruction Diseases 0.000 description 2
- 210000002700 urine Anatomy 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 description 1
- VCPGTXUFOOPLQH-WLHGVMLRSA-N (e)-but-2-enedioic acid;1-[(2,6-dimethylphenyl)methyl]-5-methyl-3-[3-[4-[2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl]propyl]pyrimidine-2,4-dione Chemical compound OC(=O)\C=C\C(O)=O.CC1=CC=CC(C)=C1CN1C(=O)N(CCCN2CCN(CC2)C=2C(=CC=CC=2)OCC(F)(F)F)C(=O)C(C)=C1 VCPGTXUFOOPLQH-WLHGVMLRSA-N 0.000 description 1
- ZPLGYKDUCAHLKQ-WLHGVMLRSA-N (e)-but-2-enedioic acid;3-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-5-methyl-1-(pyridin-2-ylmethyl)pyrimidine-2,4-dione Chemical compound OC(=O)\C=C\C(O)=O.COC1=CC=CC=C1N1CCN(CCCN2C(N(CC=3N=CC=CC=3)C=C(C)C2=O)=O)CC1 ZPLGYKDUCAHLKQ-WLHGVMLRSA-N 0.000 description 1
- RXVJZBHQWYUTQQ-WLHGVMLRSA-N (e)-but-2-enedioic acid;3-[3-[4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]propyl]-5-methyl-1-(pyridin-4-ylmethyl)pyrimidine-2,4-dione Chemical compound OC(=O)\C=C\C(O)=O.COC1=CC(F)=CC=C1N1CCN(CCCN2C(N(CC=3C=CN=CC=3)C=C(C)C2=O)=O)CC1 RXVJZBHQWYUTQQ-WLHGVMLRSA-N 0.000 description 1
- OPLZXDJZFHCCSM-WLHGVMLRSA-N (e)-but-2-enedioic acid;5-methyl-1-(pyridin-2-ylmethyl)-3-[3-[4-[2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl]propyl]pyrimidine-2,4-dione Chemical compound OC(=O)\C=C\C(O)=O.O=C1N(CCCN2CCN(CC2)C=2C(=CC=CC=2)OCC(F)(F)F)C(=O)C(C)=CN1CC1=CC=CC=N1 OPLZXDJZFHCCSM-WLHGVMLRSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- IXIKQWDDFPBBKV-UHFFFAOYSA-N 1,3-dibenzyl-5,6-dimethylpyrimidine-2,4-dione Chemical compound O=C1N(CC=2C=CC=CC=2)C(C)=C(C)C(=O)N1CC1=CC=CC=C1 IXIKQWDDFPBBKV-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GKMIDMKPBOUSBQ-UHFFFAOYSA-N 1,5-dimethyluracil Chemical compound CC1=CN(C)C(=O)NC1=O GKMIDMKPBOUSBQ-UHFFFAOYSA-N 0.000 description 1
- SATWWNUIZMDGQP-UHFFFAOYSA-N 1-(2,2-dimethyl-3-phenylmethoxypropyl)-4-[2-(2,2,2-trifluoroethoxy)phenyl]piperazine Chemical compound C1CN(C=2C(=CC=CC=2)OCC(F)(F)F)CCN1CC(C)(C)COCC1=CC=CC=C1 SATWWNUIZMDGQP-UHFFFAOYSA-N 0.000 description 1
- PJVHDXULZUFZSK-UHFFFAOYSA-N 1-(2-benzylphenyl)piperazine Chemical compound C=1C=CC=C(N2CCNCC2)C=1CC1=CC=CC=C1 PJVHDXULZUFZSK-UHFFFAOYSA-N 0.000 description 1
- AJUZXQNXDFWLGP-UHFFFAOYSA-N 1-(2-bromo-4-fluorophenyl)piperazine Chemical compound BrC1=CC(F)=CC=C1N1CCNCC1 AJUZXQNXDFWLGP-UHFFFAOYSA-N 0.000 description 1
- PWZDJIUQHUGFRJ-UHFFFAOYSA-N 1-(2-chlorophenyl)piperazine Chemical compound ClC1=CC=CC=C1N1CCNCC1 PWZDJIUQHUGFRJ-UHFFFAOYSA-N 0.000 description 1
- QOTCFLMBVLKUSS-UHFFFAOYSA-N 1-(2-cyclopropylphenyl)piperazine;dihydrochloride Chemical compound Cl.Cl.C1CC1C1=CC=CC=C1N1CCNCC1 QOTCFLMBVLKUSS-UHFFFAOYSA-N 0.000 description 1
- RKRVRTJVCWZOQS-UHFFFAOYSA-N 1-(2-diphenyl)piperazine Chemical compound C1CNCCN1C1=CC=CC=C1C1=CC=CC=C1 RKRVRTJVCWZOQS-UHFFFAOYSA-N 0.000 description 1
- DGJIEOYZRNNVDF-UHFFFAOYSA-N 1-(2-methoxy-4-methylphenyl)piperazine Chemical compound COC1=CC(C)=CC=C1N1CCNCC1 DGJIEOYZRNNVDF-UHFFFAOYSA-N 0.000 description 1
- LZXIPLMMKQLDQS-UHFFFAOYSA-N 1-(2-prop-2-ynoxyphenyl)piperazine Chemical compound C#CCOC1=CC=CC=C1N1CCNCC1 LZXIPLMMKQLDQS-UHFFFAOYSA-N 0.000 description 1
- FHIDPEUFJOUCRS-UHFFFAOYSA-N 1-(2-propylphenyl)piperazine Chemical compound CCCC1=CC=CC=C1N1CCNCC1 FHIDPEUFJOUCRS-UHFFFAOYSA-N 0.000 description 1
- GAIITEMFCPUVKJ-UHFFFAOYSA-N 1-(3-bromopropyl)-4-(4-fluoro-2-methoxyphenyl)piperazine Chemical compound COC1=CC(F)=CC=C1N1CCN(CCCBr)CC1 GAIITEMFCPUVKJ-UHFFFAOYSA-N 0.000 description 1
- UWZHLIUWMUUTMK-UHFFFAOYSA-N 1-(3-chloro-2,2-dimethylpropyl)-4-phenylpiperazine Chemical compound C1CN(CC(C)(CCl)C)CCN1C1=CC=CC=C1 UWZHLIUWMUUTMK-UHFFFAOYSA-N 0.000 description 1
- OIZBMQFOSPOOIS-UHFFFAOYSA-N 1-(3-chloropropyl)-4-(2-methoxyphenyl)piperazine Chemical compound COC1=CC=CC=C1N1CCN(CCCCl)CC1 OIZBMQFOSPOOIS-UHFFFAOYSA-N 0.000 description 1
- VYJAUUQMBVQOGV-UHFFFAOYSA-N 1-(3-chloropropyl)-5-methylpyrimidine-2,4-dione Chemical compound CC1=CN(CCCCl)C(=O)NC1=O VYJAUUQMBVQOGV-UHFFFAOYSA-N 0.000 description 1
- AYQOOVZXOFAIEW-UHFFFAOYSA-N 1-(3-chloropropyl)-6-methylpyrimidine-2,4-dione Chemical compound CC1=CC(=O)NC(=O)N1CCCCl AYQOOVZXOFAIEW-UHFFFAOYSA-N 0.000 description 1
- BUJCQWOCKGJWGX-UHFFFAOYSA-N 1-(4-fluoro-2-methoxyphenyl)piperazine;hydrochloride Chemical compound Cl.COC1=CC(F)=CC=C1N1CCNCC1 BUJCQWOCKGJWGX-UHFFFAOYSA-N 0.000 description 1
- IDPURXSQCKYKIJ-UHFFFAOYSA-N 1-(4-methoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C=C1 IDPURXSQCKYKIJ-UHFFFAOYSA-N 0.000 description 1
- FCZBQMUDGBEIHG-UHFFFAOYSA-N 1-(5-chloro-2-methoxyphenyl)piperazine Chemical compound COC1=CC=C(Cl)C=C1N1CCNCC1 FCZBQMUDGBEIHG-UHFFFAOYSA-N 0.000 description 1
- WGLUZJWOTTXZIC-UHFFFAOYSA-N 1-(bromomethyl)-2,4-dimethylbenzene Chemical compound CC1=CC=C(CBr)C(C)=C1 WGLUZJWOTTXZIC-UHFFFAOYSA-N 0.000 description 1
- WGVYCXYGPNNUQA-UHFFFAOYSA-N 1-(bromomethyl)-2-methylbenzene Chemical compound CC1=CC=CC=C1CBr WGVYCXYGPNNUQA-UHFFFAOYSA-N 0.000 description 1
- RTFPTPXBTIUISM-UHFFFAOYSA-N 1-(bromomethyl)-3-phenylbenzene Chemical compound BrCC1=CC=CC(C=2C=CC=CC=2)=C1 RTFPTPXBTIUISM-UHFFFAOYSA-N 0.000 description 1
- GIGRWGTZFONRKA-UHFFFAOYSA-N 1-(bromomethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CBr)C=C1 GIGRWGTZFONRKA-UHFFFAOYSA-N 0.000 description 1
- DMHZDOTYAVHSEH-UHFFFAOYSA-N 1-(chloromethyl)-4-methylbenzene Chemical compound CC1=CC=C(CCl)C=C1 DMHZDOTYAVHSEH-UHFFFAOYSA-N 0.000 description 1
- PSUQOGCZWBRNRZ-UHFFFAOYSA-N 1-(furan-2-yl)-5-methylpyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(C)=CN1C1=CC=CO1 PSUQOGCZWBRNRZ-UHFFFAOYSA-N 0.000 description 1
- IDKSUQDGJUQCAG-UHFFFAOYSA-N 1-(furan-2-ylmethyl)-5-methylpyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(C)=CN1CC1=CC=CO1 IDKSUQDGJUQCAG-UHFFFAOYSA-N 0.000 description 1
- BXZCGKYBKLGJGE-UHFFFAOYSA-N 1-(furan-3-ylmethyl)-5-methylpyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(C)=CN1CC1=COC=C1 BXZCGKYBKLGJGE-UHFFFAOYSA-N 0.000 description 1
- QMCQBAJOOAMKBX-UHFFFAOYSA-N 1-(hydroxymethyl)cyclopropane-1-carbonitrile Chemical compound OCC1(C#N)CC1 QMCQBAJOOAMKBX-UHFFFAOYSA-N 0.000 description 1
- DBLOUXNYTDMJBY-UHFFFAOYSA-N 1-(methoxymethyl)-5-methylpyrimidine-2,4-dione Chemical compound COCN1C=C(C)C(=O)NC1=O DBLOUXNYTDMJBY-UHFFFAOYSA-N 0.000 description 1
- HGISZXNKZIHJNJ-UHFFFAOYSA-N 1-[(2,4,5-trioxo-1,3-diazinan-1-yl)methyl]cyclopropane-1-carbonitrile Chemical class O=C1NC(=O)C(=O)CN1CC1(C#N)CC1 HGISZXNKZIHJNJ-UHFFFAOYSA-N 0.000 description 1
- QQUAJVFWOVHJNQ-UHFFFAOYSA-N 1-[(2,4,6-trioxo-1,3-diazinan-1-yl)methyl]cyclopropane-1-carbonitrile Chemical compound O=C1NC(=O)CC(=O)N1CC1(C#N)CC1 QQUAJVFWOVHJNQ-UHFFFAOYSA-N 0.000 description 1
- WIDXKYAKGRBFKF-UHFFFAOYSA-N 1-[(2,4-dimethylphenyl)methyl]-5-methylpyrimidine-2,4-dione Chemical compound CC1=CC(C)=CC=C1CN1C(=O)NC(=O)C(C)=C1 WIDXKYAKGRBFKF-UHFFFAOYSA-N 0.000 description 1
- YWAGOONDYJEWHB-UHFFFAOYSA-N 1-[(2,4-dioxopyrimidin-1-yl)methyl]cyclopropane-1-carbonitrile Chemical class O=C1NC(=O)C=CN1CC1(C#N)CC1 YWAGOONDYJEWHB-UHFFFAOYSA-N 0.000 description 1
- JTOXNJFAOBPOIS-UHFFFAOYSA-N 1-[(2-methylphenyl)methyl]-3-[3-[4-[2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl]propyl]pyrimidine-2,4-dione;hydrochloride Chemical compound Cl.CC1=CC=CC=C1CN1C(=O)N(CCCN2CCN(CC2)C=2C(=CC=CC=2)OCC(F)(F)F)C(=O)C=C1 JTOXNJFAOBPOIS-UHFFFAOYSA-N 0.000 description 1
- GNSDGNBCUGBUMI-UHFFFAOYSA-N 1-[(4-methoxyphenyl)methyl]-2,4-dioxopyrimidine-5-carbonitrile Chemical compound C1=CC(OC)=CC=C1CN1C(=O)NC(=O)C(C#N)=C1 GNSDGNBCUGBUMI-UHFFFAOYSA-N 0.000 description 1
- ONGFXPIEPBCSJA-UHFFFAOYSA-N 1-[(4-methoxyphenyl)methyl]-5-methylpyrimidine-2,4-dione Chemical compound C1=CC(OC)=CC=C1CN1C(=O)NC(=O)C(C)=C1 ONGFXPIEPBCSJA-UHFFFAOYSA-N 0.000 description 1
- NLOHYQGUQHBVTM-UHFFFAOYSA-N 1-[2,4-bis(2,2,2-trifluoroethoxy)phenyl]piperazine Chemical compound FC(F)(F)COC1=CC(OCC(F)(F)F)=CC=C1N1CCNCC1 NLOHYQGUQHBVTM-UHFFFAOYSA-N 0.000 description 1
- BYAQYSSJWRCBRM-UHFFFAOYSA-N 1-[2-(2,2-dimethylpropoxy)phenyl]piperazine Chemical compound CC(C)(C)COC1=CC=CC=C1N1CCNCC1 BYAQYSSJWRCBRM-UHFFFAOYSA-N 0.000 description 1
- VBVJJGMGUBLJPI-UHFFFAOYSA-N 1-[2-(furan-2-yl)phenyl]piperazine Chemical compound C1CNCCN1C1=CC=CC=C1C1=CC=CO1 VBVJJGMGUBLJPI-UHFFFAOYSA-N 0.000 description 1
- VZUBMIDXJRGARE-UHFFFAOYSA-N 1-[2-(trifluoromethyl)phenyl]piperazine Chemical compound FC(F)(F)C1=CC=CC=C1N1CCNCC1 VZUBMIDXJRGARE-UHFFFAOYSA-N 0.000 description 1
- MGXIOLOKSUIKJS-UHFFFAOYSA-N 1-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-5,5-dimethyl-1,3-diazinane-2,4,6-trione Chemical compound COC1=CC=CC=C1N1CCN(CCCN2C(C(C)(C)C(=O)NC2=O)=O)CC1 MGXIOLOKSUIKJS-UHFFFAOYSA-N 0.000 description 1
- WTJYAWWJAQZWHQ-UHFFFAOYSA-N 1-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-6-methylpyrimidine-2,4-dione;hydrochloride Chemical compound Cl.COC1=CC=CC=C1N1CCN(CCCN2C(NC(=O)C=C2C)=O)CC1 WTJYAWWJAQZWHQ-UHFFFAOYSA-N 0.000 description 1
- WQYNIBATGVIVLG-UHFFFAOYSA-N 1-[4-fluoro-2-(2,2,2-trifluoroethoxy)phenyl]piperazine;dihydrochloride Chemical compound Cl.Cl.FC(F)(F)COC1=CC(F)=CC=C1N1CCNCC1 WQYNIBATGVIVLG-UHFFFAOYSA-N 0.000 description 1
- QWXOEYOSHJZNHZ-UHFFFAOYSA-N 1-[4-fluoro-2-(2,2,2-trifluoroethoxy)phenyl]piperazine;hydrochloride Chemical compound Cl.FC(F)(F)COC1=CC(F)=CC=C1N1CCNCC1 QWXOEYOSHJZNHZ-UHFFFAOYSA-N 0.000 description 1
- SBSOTDPWQFOYTD-UHFFFAOYSA-N 1-[5-chloro-2-(2,2,2-trifluoroethoxy)phenyl]piperazine Chemical compound FC(F)(F)COC1=CC=C(Cl)C=C1N1CCNCC1 SBSOTDPWQFOYTD-UHFFFAOYSA-N 0.000 description 1
- QCNJNWMZHAGNJI-UHFFFAOYSA-N 1-benzyl-3-(3-chloropropyl)-2,4-dioxopyrimidine-5-carbaldehyde Chemical compound O=C1N(CCCCl)C(=O)C(C=O)=CN1CC1=CC=CC=C1 QCNJNWMZHAGNJI-UHFFFAOYSA-N 0.000 description 1
- XJLNKWUTKNBTHI-WLHGVMLRSA-N 1-benzyl-3-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-5,5-dimethyl-1,3-diazinane-2,4,6-trione;(e)-but-2-enedioic acid Chemical compound OC(=O)\C=C\C(O)=O.COC1=CC=CC=C1N1CCN(CCCN2C(C(C)(C)C(=O)N(CC=3C=CC=CC=3)C2=O)=O)CC1 XJLNKWUTKNBTHI-WLHGVMLRSA-N 0.000 description 1
- SWXACSWNXWRDLA-UHFFFAOYSA-N 1-benzyl-3-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-5-(trifluoromethyl)pyrimidine-2,4-dione Chemical compound COC1=CC=CC=C1N1CCN(CCCN2C(N(CC=3C=CC=CC=3)C=C(C2=O)C(F)(F)F)=O)CC1 SWXACSWNXWRDLA-UHFFFAOYSA-N 0.000 description 1
- ZRJOPRJEOILBIS-UHFFFAOYSA-N 1-benzyl-3-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-5-methylpyrimidine-2,4-dione Chemical compound COC1=CC=CC=C1N1CCN(CCCN2C(N(CC=3C=CC=CC=3)C=C(C)C2=O)=O)CC1 ZRJOPRJEOILBIS-UHFFFAOYSA-N 0.000 description 1
- FCPWANVAONAFJY-UHFFFAOYSA-N 1-benzyl-3-[3-[4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]propyl]-5,5-dimethyl-1,3-diazinane-2,4,6-trione Chemical compound COC1=CC(F)=CC=C1N1CCN(CCCN2C(C(C)(C)C(=O)N(CC=3C=CC=CC=3)C2=O)=O)CC1 FCPWANVAONAFJY-UHFFFAOYSA-N 0.000 description 1
- BCESLWNOUTZSKZ-UHFFFAOYSA-N 1-benzyl-5,5-dimethyl-3-[3-[4-[2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl]propyl]-1,3-diazinane-2,4,6-trione Chemical compound O=C1N(CC=2C=CC=CC=2)C(=O)C(C)(C)C(=O)N1CCCN(CC1)CCN1C1=CC=CC=C1OCC(F)(F)F BCESLWNOUTZSKZ-UHFFFAOYSA-N 0.000 description 1
- PDBBMHLDPVLUJX-UHFFFAOYSA-N 1-benzyl-5,6-dimethyl-3-[3-[4-[2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl]propyl]pyrimidine-2,4-dione Chemical compound O=C1N(CC=2C=CC=CC=2)C(C)=C(C)C(=O)N1CCCN(CC1)CCN1C1=CC=CC=C1OCC(F)(F)F PDBBMHLDPVLUJX-UHFFFAOYSA-N 0.000 description 1
- CFVALOBMBFJIQG-UHFFFAOYSA-N 1-benzyl-5,6-dimethylpyrimidine-2,4-dione Chemical compound CC1=C(C)C(=O)NC(=O)N1CC1=CC=CC=C1 CFVALOBMBFJIQG-UHFFFAOYSA-N 0.000 description 1
- YHCUSOZTGGFHME-UHFFFAOYSA-N 1-benzyl-5-(hydroxyiminomethyl)-3-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]pyrimidine-2,4-dione Chemical compound COC1=CC=CC=C1N1CCN(CCCN2C(N(CC=3C=CC=CC=3)C=C(C=NO)C2=O)=O)CC1 YHCUSOZTGGFHME-UHFFFAOYSA-N 0.000 description 1
- VOZGSDWIOZVDEB-UHFFFAOYSA-N 1-benzyl-5-(hydroxyiminomethyl)pyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(C=NO)=CN1CC1=CC=CC=C1 VOZGSDWIOZVDEB-UHFFFAOYSA-N 0.000 description 1
- AGIVMHNXXADTRF-UHFFFAOYSA-N 1-benzyl-5-(methoxymethyl)pyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(COC)=CN1CC1=CC=CC=C1 AGIVMHNXXADTRF-UHFFFAOYSA-N 0.000 description 1
- ZITBFOXDGAVSPD-UHFFFAOYSA-N 1-benzyl-5-(trifluoromethyl)pyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(C(F)(F)F)=CN1CC1=CC=CC=C1 ZITBFOXDGAVSPD-UHFFFAOYSA-N 0.000 description 1
- UPDVROAGFZMQSO-UHFFFAOYSA-N 1-benzyl-5-ethyl-3-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]pyrimidine-2,4-dione Chemical compound O=C1N(CCCN2CCN(CC2)C=2C(=CC=CC=2)OC)C(=O)C(CC)=CN1CC1=CC=CC=C1 UPDVROAGFZMQSO-UHFFFAOYSA-N 0.000 description 1
- FXZOXIZVTVVQOF-UHFFFAOYSA-N 1-benzyl-5-methyl-3-[[1-[[4-[2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl]methyl]cyclopropyl]methyl]pyrimidine-2,4-dione Chemical compound O=C1N(CC2(CN3CCN(CC3)C=3C(=CC=CC=3)OCC(F)(F)F)CC2)C(=O)C(C)=CN1CC1=CC=CC=C1 FXZOXIZVTVVQOF-UHFFFAOYSA-N 0.000 description 1
- ARFUVDRZWZNMJO-UHFFFAOYSA-N 1-benzyl-5-propyl-3-[3-[4-[2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl]propyl]pyrimidine-2,4-dione Chemical compound O=C1N(CCCN2CCN(CC2)C=2C(=CC=CC=2)OCC(F)(F)F)C(=O)C(CCC)=CN1CC1=CC=CC=C1 ARFUVDRZWZNMJO-UHFFFAOYSA-N 0.000 description 1
- GGOPSNZRSUGOSM-UHFFFAOYSA-N 1-benzyl-5-propylpyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(CCC)=CN1CC1=CC=CC=C1 GGOPSNZRSUGOSM-UHFFFAOYSA-N 0.000 description 1
- LXRVJHIISSYWEJ-UHFFFAOYSA-N 1-benzyl-6-methylpyrimidine-2,4-dione Chemical compound CC1=CC(=O)NC(=O)N1CC1=CC=CC=C1 LXRVJHIISSYWEJ-UHFFFAOYSA-N 0.000 description 1
- IQXXEPZFOOTTBA-UHFFFAOYSA-N 1-benzylpiperazine Chemical compound C=1C=CC=CC=1CN1CCNCC1 IQXXEPZFOOTTBA-UHFFFAOYSA-N 0.000 description 1
- VYBPQVFJJKEBLA-UHFFFAOYSA-N 1-benzylpyrimidine-2,4-dione Chemical compound O=C1NC(=O)C=CN1CC1=CC=CC=C1 VYBPQVFJJKEBLA-UHFFFAOYSA-N 0.000 description 1
- BASMANVIUSSIIM-UHFFFAOYSA-N 1-chloro-2-(chloromethyl)benzene Chemical compound ClCC1=CC=CC=C1Cl BASMANVIUSSIIM-UHFFFAOYSA-N 0.000 description 1
- DDGRAFHHXYIQQR-UHFFFAOYSA-N 1-chloro-3-(chloromethyl)benzene Chemical compound ClCC1=CC=CC(Cl)=C1 DDGRAFHHXYIQQR-UHFFFAOYSA-N 0.000 description 1
- NWESJZZPAJGHRZ-UHFFFAOYSA-N 1-chloro-4-methyl-2-nitrobenzene Chemical compound CC1=CC=C(Cl)C([N+]([O-])=O)=C1 NWESJZZPAJGHRZ-UHFFFAOYSA-N 0.000 description 1
- YZNQITSGDRCUKE-UHFFFAOYSA-N 1-chloropropane Chemical compound [CH2]CCCl YZNQITSGDRCUKE-UHFFFAOYSA-N 0.000 description 1
- KSJJMSKNZVXAND-UHFFFAOYSA-N 1-cyanocyclopropane-1-carboxylic acid Chemical compound OC(=O)C1(C#N)CC1 KSJJMSKNZVXAND-UHFFFAOYSA-N 0.000 description 1
- AMMPLVWPWSYRDR-UHFFFAOYSA-N 1-methylbicyclo[2.2.2]oct-2-ene-4-carboxylic acid Chemical compound C1CC2(C(O)=O)CCC1(C)C=C2 AMMPLVWPWSYRDR-UHFFFAOYSA-N 0.000 description 1
- ZBJPZNMNTXQNQQ-UHFFFAOYSA-N 2,2,2-trifluoro-n-(2-piperazin-1-ylphenyl)acetamide Chemical compound FC(F)(F)C(=O)NC1=CC=CC=C1N1CCNCC1 ZBJPZNMNTXQNQQ-UHFFFAOYSA-N 0.000 description 1
- CDTPETQAUPHIHH-UHFFFAOYSA-N 2,2-dimethyl-3-[4-[2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl]propan-1-ol Chemical compound C1CN(CC(C)(CO)C)CCN1C1=CC=CC=C1OCC(F)(F)F CDTPETQAUPHIHH-UHFFFAOYSA-N 0.000 description 1
- LGPTVHABQNQBSK-UHFFFAOYSA-N 2,2-dimethyl-3-phenylmethoxypropanoic acid Chemical compound OC(=O)C(C)(C)COCC1=CC=CC=C1 LGPTVHABQNQBSK-UHFFFAOYSA-N 0.000 description 1
- WBFGSAPRAFBOGB-UHFFFAOYSA-N 2,2-dimethyl-3-phenylmethoxypropanoyl chloride Chemical compound ClC(=O)C(C)(C)COCC1=CC=CC=C1 WBFGSAPRAFBOGB-UHFFFAOYSA-N 0.000 description 1
- CXMLRKQCTGJCBT-UHFFFAOYSA-N 2,4-bis(2,2,2-trifluoroethoxy)aniline Chemical compound NC1=CC=C(OCC(F)(F)F)C=C1OCC(F)(F)F CXMLRKQCTGJCBT-UHFFFAOYSA-N 0.000 description 1
- RJXOVESYJFXCGI-UHFFFAOYSA-N 2,4-difluoro-1-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1F RJXOVESYJFXCGI-UHFFFAOYSA-N 0.000 description 1
- PRGWGLURRQEPIC-UHFFFAOYSA-N 2-(2,2-dimethylpropoxy)aniline Chemical compound CC(C)(C)COC1=CC=CC=C1N PRGWGLURRQEPIC-UHFFFAOYSA-N 0.000 description 1
- ZCDDEIZEZFBDLR-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,3-oxazole Chemical compound FC1=CC(F)=CC=C1C1=NC=CO1 ZCDDEIZEZFBDLR-UHFFFAOYSA-N 0.000 description 1
- ZXHPYFGYSFLVGM-UHFFFAOYSA-N 2-(3-chloropropyl)-6-methyl-4-(2-trimethylsilylethoxymethyl)-1,2,4-triazine-3,5-dione Chemical compound CC1=NN(CCCCl)C(=O)N(COCC[Si](C)(C)C)C1=O ZXHPYFGYSFLVGM-UHFFFAOYSA-N 0.000 description 1
- YGTUPRIZNBMOFV-UHFFFAOYSA-N 2-(4-hydroxybenzoyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=C(O)C=C1 YGTUPRIZNBMOFV-UHFFFAOYSA-N 0.000 description 1
- HPVRFWQMBYLJRL-UHFFFAOYSA-N 2-(chloromethyl)-1,3-dimethylbenzene Chemical compound CC1=CC=CC(C)=C1CCl HPVRFWQMBYLJRL-UHFFFAOYSA-N 0.000 description 1
- GFHPSQFCHUIFTO-UHFFFAOYSA-N 2-(chloromethyl)pyrazine Chemical compound ClCC1=CN=CC=N1 GFHPSQFCHUIFTO-UHFFFAOYSA-N 0.000 description 1
- JPMRGPPMXHGKRO-UHFFFAOYSA-N 2-(chloromethyl)pyridine hydrochloride Chemical compound Cl.ClCC1=CC=CC=N1 JPMRGPPMXHGKRO-UHFFFAOYSA-N 0.000 description 1
- ZFCOUBUSGHLCDT-UHFFFAOYSA-N 2-(trifluoromethoxy)aniline Chemical compound NC1=CC=CC=C1OC(F)(F)F ZFCOUBUSGHLCDT-UHFFFAOYSA-N 0.000 description 1
- VBLXCTYLWZJBKA-UHFFFAOYSA-N 2-(trifluoromethyl)aniline Chemical compound NC1=CC=CC=C1C(F)(F)F VBLXCTYLWZJBKA-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- DWOBGCPUQNFAFB-UHFFFAOYSA-N 2-benzylaniline Chemical compound NC1=CC=CC=C1CC1=CC=CC=C1 DWOBGCPUQNFAFB-UHFFFAOYSA-N 0.000 description 1
- YLMFXCIATJJKQL-UHFFFAOYSA-N 2-bromo-4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1Br YLMFXCIATJJKQL-UHFFFAOYSA-N 0.000 description 1
- QDIOFUNDCFWOJY-UHFFFAOYSA-N 2-cyano-2-methoxycarbonylbutanoic acid Chemical compound CCC(C#N)(C(=O)O)C(=O)OC QDIOFUNDCFWOJY-UHFFFAOYSA-N 0.000 description 1
- QJQZRLXDLORINA-UHFFFAOYSA-N 2-cyclohexylethanol Chemical compound OCCC1CCCCC1 QJQZRLXDLORINA-UHFFFAOYSA-N 0.000 description 1
- JSKOLQWFMXYJAF-UHFFFAOYSA-N 2-cyclopropylaniline Chemical compound NC1=CC=CC=C1C1CC1 JSKOLQWFMXYJAF-UHFFFAOYSA-N 0.000 description 1
- CNNNOMZFRQSTMF-UHFFFAOYSA-N 2-ethoxy-4-fluoroaniline Chemical compound CCOC1=CC(F)=CC=C1N CNNNOMZFRQSTMF-UHFFFAOYSA-N 0.000 description 1
- NSTREUWFTAOOKS-UHFFFAOYSA-N 2-fluorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1F NSTREUWFTAOOKS-UHFFFAOYSA-N 0.000 description 1
- RAAGZOYMEQDCTD-UHFFFAOYSA-N 2-fluorobenzoyl chloride Chemical compound FC1=CC=CC=C1C(Cl)=O RAAGZOYMEQDCTD-UHFFFAOYSA-N 0.000 description 1
- UPHOPMSGKZNELG-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=C(O)C=CC2=C1 UPHOPMSGKZNELG-UHFFFAOYSA-N 0.000 description 1
- CJJLEUQMMMLOFI-UHFFFAOYSA-N 2-methoxy-4-methylaniline Chemical compound COC1=CC(C)=CC=C1N CJJLEUQMMMLOFI-UHFFFAOYSA-N 0.000 description 1
- TWBPWBPGNQWFSJ-UHFFFAOYSA-N 2-phenylaniline Chemical group NC1=CC=CC=C1C1=CC=CC=C1 TWBPWBPGNQWFSJ-UHFFFAOYSA-N 0.000 description 1
- TZWRXFPFRACRLO-UHFFFAOYSA-N 2-piperazin-1-ylaniline Chemical compound NC1=CC=CC=C1N1CCNCC1 TZWRXFPFRACRLO-UHFFFAOYSA-N 0.000 description 1
- DRGLRUYXGNMDDM-UHFFFAOYSA-N 2-prop-2-ynoxyaniline Chemical compound NC1=CC=CC=C1OCC#C DRGLRUYXGNMDDM-UHFFFAOYSA-N 0.000 description 1
- WKURVXXDGMYSDP-UHFFFAOYSA-N 2-propyl-aniline Chemical compound CCCC1=CC=CC=C1N WKURVXXDGMYSDP-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- MSWDQTIXBKDFQK-UHFFFAOYSA-N 3-(3-chloropropyl)-1,5-dimethylpyrimidine-2,4-dione Chemical compound CC1=CN(C)C(=O)N(CCCCl)C1=O MSWDQTIXBKDFQK-UHFFFAOYSA-N 0.000 description 1
- ZEFHWMVTDXRWDV-UHFFFAOYSA-N 3-(3-chloropropyl)-1-(4-fluorophenyl)-5-methylpyrimidine-2,4-dione Chemical compound O=C1N(CCCCl)C(=O)C(C)=CN1C1=CC=C(F)C=C1 ZEFHWMVTDXRWDV-UHFFFAOYSA-N 0.000 description 1
- WALIDKWLARMQDS-UHFFFAOYSA-N 3-(3-chloropropyl)-1-(furan-2-yl)-5-methylpyrimidine-2,4-dione Chemical compound O=C1N(CCCCl)C(=O)C(C)=CN1C1=CC=CO1 WALIDKWLARMQDS-UHFFFAOYSA-N 0.000 description 1
- WCNMRIPVTWZNIE-UHFFFAOYSA-N 3-(3-chloropropyl)-1-(methoxymethyl)-5-methylpyrimidine-2,4-dione Chemical compound COCN1C=C(C)C(=O)N(CCCCl)C1=O WCNMRIPVTWZNIE-UHFFFAOYSA-N 0.000 description 1
- SUHFCHJPOMKAAM-UHFFFAOYSA-N 3-(3-chloropropyl)-1-[(2,4-dimethylphenyl)methyl]-5-methylpyrimidine-2,4-dione Chemical compound CC1=CC(C)=CC=C1CN1C(=O)N(CCCCl)C(=O)C(C)=C1 SUHFCHJPOMKAAM-UHFFFAOYSA-N 0.000 description 1
- ITWJTPYWVIUAMT-UHFFFAOYSA-N 3-(3-chloropropyl)-1-[(4-methoxyphenyl)methyl]-2,4-dioxopyrimidine-5-carbonitrile Chemical compound C1=CC(OC)=CC=C1CN1C(=O)N(CCCCl)C(=O)C(C#N)=C1 ITWJTPYWVIUAMT-UHFFFAOYSA-N 0.000 description 1
- NJOQWSUODZNKRR-UHFFFAOYSA-N 3-(3-chloropropyl)-1-[(4-methoxyphenyl)methyl]-5-methylpyrimidine-2,4-dione Chemical compound C1=CC(OC)=CC=C1CN1C(=O)N(CCCCl)C(=O)C(C)=C1 NJOQWSUODZNKRR-UHFFFAOYSA-N 0.000 description 1
- SBKJPFDHNJHGGP-UHFFFAOYSA-N 3-(3-chloropropyl)-5-methyl-1-(2,2,2-trifluoroethoxy)pyrimidine-2,4-dione Chemical compound CC1=CN(OCC(F)(F)F)C(=O)N(CCCCl)C1=O SBKJPFDHNJHGGP-UHFFFAOYSA-N 0.000 description 1
- WZMTUJFTKVUAEJ-UHFFFAOYSA-N 3-(3-chloropropyl)-5-methyl-1-(pyridin-3-ylmethyl)pyrimidine-2,4-dione Chemical compound O=C1N(CCCCl)C(=O)C(C)=CN1CC1=CC=CN=C1 WZMTUJFTKVUAEJ-UHFFFAOYSA-N 0.000 description 1
- XNCKTAZIZRMRRJ-UHFFFAOYSA-N 3-(3-chloropropyl)-5-methyl-1-[(1-oxidopyridin-1-ium-2-yl)methyl]pyrimidine-2,4-dione Chemical compound ClCCCN1C(N(C=C(C1=O)C)CC1=[N+](C=CC=C1)[O-])=O XNCKTAZIZRMRRJ-UHFFFAOYSA-N 0.000 description 1
- JAWRNWRGPRLQGG-UHFFFAOYSA-N 3-(3-chloropropyl)-5-methyl-1-phenylpyrimidine-2,4-dione Chemical compound O=C1N(CCCCl)C(=O)C(C)=CN1C1=CC=CC=C1 JAWRNWRGPRLQGG-UHFFFAOYSA-N 0.000 description 1
- WAGPVAJQFZHWCY-UHFFFAOYSA-N 3-(3-chloropropyl)-5-methyl-1-thiophen-2-ylpyrimidine-2,4-dione Chemical compound O=C1N(CCCCl)C(=O)C(C)=CN1C1=CC=CS1 WAGPVAJQFZHWCY-UHFFFAOYSA-N 0.000 description 1
- NXFZZHAHHVCGGR-UHFFFAOYSA-N 3-(4-fluorophenyl)-5-methyl-1-[3-[4-[2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl]propyl]pyrimidine-2,4-dione;hydrochloride Chemical compound Cl.O=C1N(C=2C=CC(F)=CC=2)C(=O)C(C)=CN1CCCN(CC1)CCN1C1=CC=CC=C1OCC(F)(F)F NXFZZHAHHVCGGR-UHFFFAOYSA-N 0.000 description 1
- FVDLNAXEKGVOIT-UHFFFAOYSA-N 3-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-1,5-dimethylpyrimidine-2,4-dione Chemical compound COC1=CC=CC=C1N1CCN(CCCN2C(N(C)C=C(C)C2=O)=O)CC1 FVDLNAXEKGVOIT-UHFFFAOYSA-N 0.000 description 1
- RLVDLEWLVVSUFL-UHFFFAOYSA-N 3-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-1,5-dimethylpyrimidine-2,4-dione;hydrochloride Chemical compound Cl.COC1=CC=CC=C1N1CCN(CCCN2C(N(C)C=C(C)C2=O)=O)CC1 RLVDLEWLVVSUFL-UHFFFAOYSA-N 0.000 description 1
- LROWWOHMIMKKFX-UHFFFAOYSA-N 3-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-5,6,7,8-tetrahydro-1h-quinazoline-2,4-dione Chemical compound COC1=CC=CC=C1N1CCN(CCCN2C(C=3CCCCC=3NC2=O)=O)CC1 LROWWOHMIMKKFX-UHFFFAOYSA-N 0.000 description 1
- RSRPHCIXRXEIHM-UHFFFAOYSA-N 3-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-5-methyl-1h-pyrimidine-2,4-dione;hydrochloride Chemical compound Cl.COC1=CC=CC=C1N1CCN(CCCN2C(C(C)=CNC2=O)=O)CC1 RSRPHCIXRXEIHM-UHFFFAOYSA-N 0.000 description 1
- XLJFVLRFWBYNTM-UHFFFAOYSA-N 3-[3-[4-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]propyl]-5,6,7,8-tetrahydro-1h-quinazoline-2,4-dione Chemical compound COC1=CC(F)=CC=C1N1CCN(CCCN2C(C=3CCCCC=3NC2=O)=O)CC1 XLJFVLRFWBYNTM-UHFFFAOYSA-N 0.000 description 1
- WJBLDBYANYMZEU-UHFFFAOYSA-N 3-[3-[4-[2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl]propyl]-5,6,7,8-tetrahydro-1h-quinazoline-2,4-dione Chemical compound FC(F)(F)COC1=CC=CC=C1N1CCN(CCCN2C(C=3CCCCC=3NC2=O)=O)CC1 WJBLDBYANYMZEU-UHFFFAOYSA-N 0.000 description 1
- XHJBPGUISSFWJF-UHFFFAOYSA-N 3-[3-[4-[4-fluoro-2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl]propyl]-1-(2-trimethylsilylethoxymethyl)pyrimidine-2,4-dione Chemical compound O=C1N(COCC[Si](C)(C)C)C=CC(=O)N1CCCN1CCN(C=2C(=CC(F)=CC=2)OCC(F)(F)F)CC1 XHJBPGUISSFWJF-UHFFFAOYSA-N 0.000 description 1
- WEZFJPKJUIGDPS-UHFFFAOYSA-N 3-[3-[4-[4-fluoro-2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl]propyl]-5-methyl-1h-pyrimidine-2,4-dione Chemical compound O=C1C(C)=CNC(=O)N1CCCN1CCN(C=2C(=CC(F)=CC=2)OCC(F)(F)F)CC1 WEZFJPKJUIGDPS-UHFFFAOYSA-N 0.000 description 1
- HCFPXCCGFLBAKV-UHFFFAOYSA-N 3-benzyl-1-(3-chloropropyl)-5,6-dimethylpyrimidine-2,4-dione Chemical compound O=C1N(CCCCl)C(C)=C(C)C(=O)N1CC1=CC=CC=C1 HCFPXCCGFLBAKV-UHFFFAOYSA-N 0.000 description 1
- POSBFKDBNZDBLA-UHFFFAOYSA-N 3-benzyl-1-(3-chloropropyl)-5-methylpyrimidine-2,4-dione Chemical compound O=C1C(C)=CN(CCCCl)C(=O)N1CC1=CC=CC=C1 POSBFKDBNZDBLA-UHFFFAOYSA-N 0.000 description 1
- BFNZFGPAQOISDE-UHFFFAOYSA-N 3-benzyl-1-(3-chloropropyl)-6-methylpyrimidine-2,4-dione Chemical compound O=C1N(CCCCl)C(C)=CC(=O)N1CC1=CC=CC=C1 BFNZFGPAQOISDE-UHFFFAOYSA-N 0.000 description 1
- WOVFHBWDKRSMOZ-UHFFFAOYSA-N 3-benzyl-1-[3-[4-[4-chloro-2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl]propyl]-5-methylpyrimidine-2,4-dione;hydrochloride Chemical compound Cl.O=C1N(CC=2C=CC=CC=2)C(=O)C(C)=CN1CCCN(CC1)CCN1C1=CC=C(Cl)C=C1OCC(F)(F)F WOVFHBWDKRSMOZ-UHFFFAOYSA-N 0.000 description 1
- ZZLRALMLEUWXII-UHFFFAOYSA-N 3-benzyl-5-methyl-2,6-dioxopyrimidine-4-carbonitrile Chemical compound O=C1NC(=O)C(C)=C(C#N)N1CC1=CC=CC=C1 ZZLRALMLEUWXII-UHFFFAOYSA-N 0.000 description 1
- ZRPLANDPDWYOMZ-UHFFFAOYSA-N 3-cyclopentylpropionic acid Chemical compound OC(=O)CCC1CCCC1 ZRPLANDPDWYOMZ-UHFFFAOYSA-N 0.000 description 1
- RDFQSFOGKVZWKF-UHFFFAOYSA-N 3-hydroxy-2,2-dimethylpropanoic acid Chemical compound OCC(C)(C)C(O)=O RDFQSFOGKVZWKF-UHFFFAOYSA-N 0.000 description 1
- VVZRUVXWXQVKMU-UHFFFAOYSA-N 4-(3-chloropropyl)-6-methyl-2h-1,2,4-triazine-3,5-dione Chemical compound CC1=NNC(=O)N(CCCCl)C1=O VVZRUVXWXQVKMU-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- ZUHNOPCGQHCJST-UHFFFAOYSA-N 4-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-6-methyl-2h-1,2,4-triazine-3,5-dione Chemical compound COC1=CC=CC=C1N1CCN(CCCN2C(C(C)=NNC2=O)=O)CC1 ZUHNOPCGQHCJST-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- KLRUDTNBNBHCES-UHFFFAOYSA-N 4-chloro-2-(2,2,2-trifluoroethoxy)aniline Chemical compound NC1=CC=C(Cl)C=C1OCC(F)(F)F KLRUDTNBNBHCES-UHFFFAOYSA-N 0.000 description 1
- WOXLPNAOCCIZGP-UHFFFAOYSA-N 4-chloro-2-methoxyaniline Chemical compound COC1=CC(Cl)=CC=C1N WOXLPNAOCCIZGP-UHFFFAOYSA-N 0.000 description 1
- RJWBTWIBUIGANW-UHFFFAOYSA-N 4-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Cl)C=C1 RJWBTWIBUIGANW-UHFFFAOYSA-N 0.000 description 1
- LFNMZMIRGLYATQ-UHFFFAOYSA-N 4-fluoro-2-(2,2,2-trifluoroethoxy)aniline;hydrochloride Chemical compound Cl.NC1=CC=C(F)C=C1OCC(F)(F)F LFNMZMIRGLYATQ-UHFFFAOYSA-N 0.000 description 1
- BNRRMRUVYDETQC-UHFFFAOYSA-N 4-fluoro-2-methoxyaniline Chemical compound COC1=CC(F)=CC=C1N BNRRMRUVYDETQC-UHFFFAOYSA-N 0.000 description 1
- JYUNCPZWAAYAMT-UHFFFAOYSA-N 4-methoxy-2-(2,2,2-trifluoroethoxy)aniline Chemical compound COC1=CC=C(N)C(OCC(F)(F)F)=C1 JYUNCPZWAAYAMT-UHFFFAOYSA-N 0.000 description 1
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 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
- YSVIJBXNRJVSBO-UHFFFAOYSA-N 4-methyl-2-(2,2,2-trifluoroethoxy)aniline Chemical compound CC1=CC=C(N)C(OCC(F)(F)F)=C1 YSVIJBXNRJVSBO-UHFFFAOYSA-N 0.000 description 1
- WPJKLUJKTVCEOC-UHFFFAOYSA-N 4-piperazin-1-yl-3-(2,2,2-trifluoroethoxy)phenol;hydrobromide Chemical compound Br.FC(F)(F)COC1=CC(O)=CC=C1N1CCNCC1 WPJKLUJKTVCEOC-UHFFFAOYSA-N 0.000 description 1
- AWQSAIIDOMEEOD-UHFFFAOYSA-N 5,5-Dimethyl-4-(3-oxobutyl)dihydro-2(3H)-furanone Chemical compound CC(=O)CCC1CC(=O)OC1(C)C AWQSAIIDOMEEOD-UHFFFAOYSA-N 0.000 description 1
- PZVLJGKJIMBYNP-UHFFFAOYSA-N 5,6-dimethyl-1h-pyrimidine-2,4-dione Chemical compound CC=1NC(=O)NC(=O)C=1C PZVLJGKJIMBYNP-UHFFFAOYSA-N 0.000 description 1
- ZULKEHIQGFUQJA-UHFFFAOYSA-N 5,6-dimethyl-3-[3-[4-[2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl]propyl]-1h-pyrimidine-2,4-dione;hydrochloride Chemical compound Cl.O=C1C(C)=C(C)NC(=O)N1CCCN1CCN(C=2C(=CC=CC=2)OCC(F)(F)F)CC1 ZULKEHIQGFUQJA-UHFFFAOYSA-N 0.000 description 1
- BMCOODRJVHNWFL-UHFFFAOYSA-N 5-(furan-2-yl)-1h-pyrimidine-2,4-dione Chemical compound O=C1NC(=O)NC=C1C1=CC=CO1 BMCOODRJVHNWFL-UHFFFAOYSA-N 0.000 description 1
- CHQMVIQFSZGTLL-UHFFFAOYSA-N 5-(hydroxymethyl)-1-(2-trimethylsilylethoxymethyl)pyrimidine-2,4-dione Chemical compound C[Si](C)(C)CCOCN1C=C(CO)C(=O)NC1=O CHQMVIQFSZGTLL-UHFFFAOYSA-N 0.000 description 1
- LMNPKIOZMGYQIU-UHFFFAOYSA-N 5-(trifluoromethyl)-1h-pyrimidine-2,4-dione Chemical compound FC(F)(F)C1=CNC(=O)NC1=O LMNPKIOZMGYQIU-UHFFFAOYSA-N 0.000 description 1
- QVHQVFPXAKZMKQ-UHFFFAOYSA-N 5-chloro-2-(2,2,2-trifluoroethoxy)aniline Chemical compound NC1=CC(Cl)=CC=C1OCC(F)(F)F QVHQVFPXAKZMKQ-UHFFFAOYSA-N 0.000 description 1
- WBSMIPLNPSCJFS-UHFFFAOYSA-N 5-chloro-2-methoxyaniline Chemical compound COC1=CC=C(Cl)C=C1N WBSMIPLNPSCJFS-UHFFFAOYSA-N 0.000 description 1
- KXLVCUSSQHHGNR-UHFFFAOYSA-N 5-chloro-3-[3-[4-[4-fluoro-2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl]propyl]-1-(2-trimethylsilylethoxymethyl)pyrimidine-2,4-dione Chemical compound O=C1N(COCC[Si](C)(C)C)C=C(Cl)C(=O)N1CCCN1CCN(C=2C(=CC(F)=CC=2)OCC(F)(F)F)CC1 KXLVCUSSQHHGNR-UHFFFAOYSA-N 0.000 description 1
- RHIULBJJKFDJPR-UHFFFAOYSA-N 5-ethyl-1h-pyrimidine-2,4-dione Chemical compound CCC1=CNC(=O)NC1=O RHIULBJJKFDJPR-UHFFFAOYSA-N 0.000 description 1
- VYZUBHRSGQAROM-UHFFFAOYSA-N 5-fluoro-2-methoxyaniline Chemical compound COC1=CC=C(F)C=C1N VYZUBHRSGQAROM-UHFFFAOYSA-N 0.000 description 1
- ZQPGLIGYYDGKJX-UHFFFAOYSA-N 5-fluoro-2-piperazin-1-ylphenol Chemical compound OC1=CC(F)=CC=C1N1CCNCC1 ZQPGLIGYYDGKJX-UHFFFAOYSA-N 0.000 description 1
- OFJNVANOCZHTMW-UHFFFAOYSA-N 5-hydroxyuracil Chemical compound OC1=CNC(=O)NC1=O OFJNVANOCZHTMW-UHFFFAOYSA-N 0.000 description 1
- YRFVHXFXPIWDIY-UHFFFAOYSA-N 5-methyl-1-(2,2,2-trifluoroethoxy)pyrimidine-2,4-dione Chemical compound CC1=CN(OCC(F)(F)F)C(=O)NC1=O YRFVHXFXPIWDIY-UHFFFAOYSA-N 0.000 description 1
- WPUHPDHSMHZQLG-UHFFFAOYSA-N 5-methyl-1-(pyridin-3-ylmethyl)pyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(C)=CN1CC1=CC=CN=C1 WPUHPDHSMHZQLG-UHFFFAOYSA-N 0.000 description 1
- NEFNYUWFSJJRJI-UHFFFAOYSA-N 5-methyl-1-(pyridin-4-ylmethyl)pyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(C)=CN1CC1=CC=NC=C1 NEFNYUWFSJJRJI-UHFFFAOYSA-N 0.000 description 1
- VJTKLEVFMNHOJA-UHFFFAOYSA-N 5-methyl-1-(thiophen-2-ylmethyl)pyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(C)=CN1CC1=CC=CS1 VJTKLEVFMNHOJA-UHFFFAOYSA-N 0.000 description 1
- CQQIFBDVEGXOCY-UHFFFAOYSA-N 5-methyl-1-[(2-methylphenyl)methyl]pyrimidine-2,4-dione Chemical compound CC1=CC=CC=C1CN1C(=O)NC(=O)C(C)=C1 CQQIFBDVEGXOCY-UHFFFAOYSA-N 0.000 description 1
- GBVSUBMVPPUAKP-UHFFFAOYSA-N 5-methyl-1-[(4-methylphenyl)methyl]-3-[3-[4-[2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl]propyl]pyrimidine-2,4-dione;hydrochloride Chemical compound Cl.C1=CC(C)=CC=C1CN1C(=O)N(CCCN2CCN(CC2)C=2C(=CC=CC=2)OCC(F)(F)F)C(=O)C(C)=C1 GBVSUBMVPPUAKP-UHFFFAOYSA-N 0.000 description 1
- JFIGUZOJHCKWSU-UHFFFAOYSA-N 5-methyl-1-phenylpyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(C)=CN1C1=CC=CC=C1 JFIGUZOJHCKWSU-UHFFFAOYSA-N 0.000 description 1
- UQRBNNWZKTVFAI-UHFFFAOYSA-N 5-methyl-1-thiophen-2-ylpyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(C)=CN1C1=CC=CS1 UQRBNNWZKTVFAI-UHFFFAOYSA-N 0.000 description 1
- SYBNDVDVTYSHRH-UHFFFAOYSA-N 5-methyl-2,4-dioxo-1h-pyrimidine-6-carbonitrile Chemical compound CC1=C(C#N)NC(=O)NC1=O SYBNDVDVTYSHRH-UHFFFAOYSA-N 0.000 description 1
- OUDZNGCEPBQBPX-UHFFFAOYSA-N 5-methyl-3-[3-[4-(2-pyrrol-1-ylphenyl)piperazin-1-yl]propyl]-1h-pyrimidine-2,4-dione;hydrobromide Chemical compound Br.O=C1C(C)=CNC(=O)N1CCCN1CCN(C=2C(=CC=CC=2)N2C=CC=C2)CC1 OUDZNGCEPBQBPX-UHFFFAOYSA-N 0.000 description 1
- RTXGOPLWWDOBCP-UHFFFAOYSA-N 5-methyl-3-[3-[4-[4-methyl-2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl]propyl]-1h-pyrimidine-2,4-dione;hydrobromide Chemical compound Br.FC(F)(F)COC1=CC(C)=CC=C1N1CCN(CCCN2C(C(C)=CNC2=O)=O)CC1 RTXGOPLWWDOBCP-UHFFFAOYSA-N 0.000 description 1
- SZDCYPWIIXFPEL-UHFFFAOYSA-N 5-methyl-3-phenyl-1h-pyrimidine-2,4-dione Chemical compound O=C1C(C)=CNC(=O)N1C1=CC=CC=C1 SZDCYPWIIXFPEL-UHFFFAOYSA-N 0.000 description 1
- HIDROJVLHKPMPH-UHFFFAOYSA-N 5-methylsulfanyl-1h-pyrimidine-2,4-dione Chemical compound CSC1=CNC(=O)NC1=O HIDROJVLHKPMPH-UHFFFAOYSA-N 0.000 description 1
- JHEKLAXXCHLMNM-UHFFFAOYSA-N 5-propyl-1h-pyrimidine-2,4-dione Chemical compound CCCC1=CNC(=O)NC1=O JHEKLAXXCHLMNM-UHFFFAOYSA-N 0.000 description 1
- ITAMKJRHUSOCKZ-UHFFFAOYSA-N 6-(chloromethyl)-1,6-dimethylcyclohexa-1,3-diene Chemical compound CC1=CC=CCC1(C)CCl ITAMKJRHUSOCKZ-UHFFFAOYSA-N 0.000 description 1
- XZWMZFQOHTWGQE-UHFFFAOYSA-N 6-azathymine Chemical compound CC1=NNC(=O)NC1=O XZWMZFQOHTWGQE-UHFFFAOYSA-N 0.000 description 1
- MRFKIRFLQOAZMB-UHFFFAOYSA-N 6-methyl-3-[3-[4-[2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl]propyl]-1h-pyrimidine-2,4-dione;hydrochloride Chemical compound Cl.O=C1NC(C)=CC(=O)N1CCCN1CCN(C=2C(=CC=CC=2)OCC(F)(F)F)CC1 MRFKIRFLQOAZMB-UHFFFAOYSA-N 0.000 description 1
- DMNNXVLYOZQXCA-UHFFFAOYSA-N 6-methyl-6-(2,2,2-trifluoroethoxy)cyclohexa-2,4-dien-1-amine Chemical compound FC(F)(F)COC1(C)C=CC=CC1N DMNNXVLYOZQXCA-UHFFFAOYSA-N 0.000 description 1
- SHVCSCWHWMSGTE-UHFFFAOYSA-N 6-methyluracil Chemical compound CC1=CC(=O)NC(=O)N1 SHVCSCWHWMSGTE-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 241001631457 Cannula Species 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000282994 Cervidae Species 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 241000272496 Galliformes Species 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
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- TXXHDPDFNKHHGW-CCAGOZQPSA-N Muconic acid Natural products OC(=O)\C=C/C=C\C(O)=O TXXHDPDFNKHHGW-CCAGOZQPSA-N 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 238000007013 Reimer-Tiemann formylation reaction Methods 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 1
- 235000012545 Vaccinium macrocarpon Nutrition 0.000 description 1
- 240000001717 Vaccinium macrocarpon Species 0.000 description 1
- 235000002118 Vaccinium oxycoccus Nutrition 0.000 description 1
- VBSDVRVONBVCRO-UHFFFAOYSA-N [1-[(3-benzyl-5-methyl-2,6-dioxopyrimidin-1-yl)methyl]cyclopropyl]methyl methanesulfonate Chemical compound O=C1N(CC2(COS(C)(=O)=O)CC2)C(=O)C(C)=CN1CC1=CC=CC=C1 VBSDVRVONBVCRO-UHFFFAOYSA-N 0.000 description 1
- YSVZGWAJIHWNQK-UHFFFAOYSA-N [3-(hydroxymethyl)-2-bicyclo[2.2.1]heptanyl]methanol Chemical compound C1CC2C(CO)C(CO)C1C2 YSVZGWAJIHWNQK-UHFFFAOYSA-N 0.000 description 1
- 230000003187 abdominal effect Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- GPWHDDKQSYOYBF-UHFFFAOYSA-N ac1l2u0q Chemical compound Br[Br-]Br GPWHDDKQSYOYBF-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000001949 anaesthesia Methods 0.000 description 1
- MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 210000000709 aorta Anatomy 0.000 description 1
- 210000000702 aorta abdominal Anatomy 0.000 description 1
- 210000002376 aorta thoracic Anatomy 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 1
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 238000009835 boiling Methods 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
- 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
- 239000004202 carbamide Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000004634 cranberry Nutrition 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- GUDMZGLFZNLYEY-UHFFFAOYSA-N cyclopropylmethanol Chemical compound OCC1CC1 GUDMZGLFZNLYEY-UHFFFAOYSA-N 0.000 description 1
- 239000012649 demethylating agent Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000035487 diastolic blood pressure Effects 0.000 description 1
- 230000003205 diastolic effect Effects 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- UELKSYXXNGHTSE-UHFFFAOYSA-N diethyl 2,2-dimethylpropanedioate Chemical compound CCOC(=O)C(C)(C)C(=O)OCC UELKSYXXNGHTSE-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- FGSGHBPKHFDJOP-UHFFFAOYSA-N ethyl 2-oxocyclohexane-1-carboxylate Chemical compound CCOC(=O)C1CCCCC1=O FGSGHBPKHFDJOP-UHFFFAOYSA-N 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000006005 fluoroethoxy group Chemical group 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000000640 hydroxylating effect Effects 0.000 description 1
- 230000033444 hydroxylation Effects 0.000 description 1
- 238000005805 hydroxylation reaction Methods 0.000 description 1
- 208000013403 hyperactivity Diseases 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- WULGDPCILKQNKK-UHFFFAOYSA-N lithium piperazin-4-ide Chemical compound [Li+].C1C[N-]CCN1 WULGDPCILKQNKK-UHFFFAOYSA-N 0.000 description 1
- NJUIBIZGVANPSZ-UHFFFAOYSA-N lithium;1-benzylpiperazin-4-ide Chemical compound [Li+].C=1C=CC=CC=1CN1CC[N-]CC1 NJUIBIZGVANPSZ-UHFFFAOYSA-N 0.000 description 1
- 210000004072 lung Anatomy 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
- 230000007246 mechanism Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- GZUXJHMPEANEGY-UHFFFAOYSA-N methyl bromide Substances BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 239000012022 methylating agents Substances 0.000 description 1
- 230000001035 methylating effect Effects 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 210000002464 muscle smooth vascular Anatomy 0.000 description 1
- 210000001087 myotubule Anatomy 0.000 description 1
- YWBWHUHKSASUBK-UHFFFAOYSA-N n-(2-aminophenyl)-2,2,2-trifluoroacetamide Chemical compound NC1=CC=CC=C1NC(=O)C(F)(F)F YWBWHUHKSASUBK-UHFFFAOYSA-N 0.000 description 1
- MPXAYYWSDIKNTP-UHFFFAOYSA-N n-(2-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC=C1N MPXAYYWSDIKNTP-UHFFFAOYSA-N 0.000 description 1
- GQOSSOMLRYHEIG-UHFFFAOYSA-N n-(2-piperazin-1-ylphenyl)acetamide Chemical compound CC(=O)NC1=CC=CC=C1N1CCNCC1 GQOSSOMLRYHEIG-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
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000005181 nitrobenzenes Chemical class 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- GUWZGMWHDAJAOC-UHFFFAOYSA-N oxoplatinum;hydrate Chemical compound O.[Pt]=O GUWZGMWHDAJAOC-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 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
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical class C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 230000001144 postural effect Effects 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- WSHYKIAQCMIPTB-UHFFFAOYSA-M potassium;2-oxo-3-(3-oxo-1-phenylbutyl)chromen-4-olate Chemical compound [K+].[O-]C=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 WSHYKIAQCMIPTB-UHFFFAOYSA-M 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- SHNUBALDGXWUJI-UHFFFAOYSA-N pyridin-2-ylmethanol Chemical compound OCC1=CC=CC=N1 SHNUBALDGXWUJI-UHFFFAOYSA-N 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 238000011472 radical prostatectomy Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000010956 selective crystallization Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- IFTAKGQVGVFOJT-UHFFFAOYSA-N tert-butyl 2,4-dioxo-5-propan-2-ylpyrimidine-1-carboxylate Chemical compound CC(C)C1=CN(C(=O)OC(C)(C)C)C(=O)NC1=O IFTAKGQVGVFOJT-UHFFFAOYSA-N 0.000 description 1
- BFKXYBJKWUBHQT-UHFFFAOYSA-N tert-butyl 3-(3-chloropropyl)-5-(furan-2-yl)-2,4-dioxopyrimidine-1-carboxylate Chemical compound O=C1N(CCCCl)C(=O)N(C(=O)OC(C)(C)C)C=C1C1=CC=CO1 BFKXYBJKWUBHQT-UHFFFAOYSA-N 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
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000005297 thienyloxy group Chemical group S1C(=CC=C1)O* 0.000 description 1
- ZEMGGZBWXRYJHK-UHFFFAOYSA-N thiouracil Chemical compound O=C1C=CNC(=S)N1 ZEMGGZBWXRYJHK-UHFFFAOYSA-N 0.000 description 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
- 238000009901 transfer hydrogenation reaction Methods 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- QHUNJMXHQHHWQP-UHFFFAOYSA-N trimethylsilyl acetate Chemical compound CC(=O)O[Si](C)(C)C QHUNJMXHQHHWQP-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other 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
- C07D239/553—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other 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 with halogen atoms or nitro radicals directly attached to ring carbon atoms, e.g. fluorouracil
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other 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
- C07D239/557—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other 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 with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. orotic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/60—Three or more oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
- C07D239/96—Two oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
- C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
- C07D253/07—1,2,4-Triazines having three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D253/075—Two hetero atoms, in positions 3 and 5
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US48918395A | 1995-06-09 | 1995-06-09 |
Publications (3)
Publication Number | Publication Date |
---|---|
NO962412D0 NO962412D0 (no) | 1996-06-07 |
NO962412L NO962412L (no) | 1996-12-10 |
NO309424B1 true NO309424B1 (no) | 2001-01-29 |
Family
ID=23942748
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO962412A NO309424B1 (no) | 1995-06-09 | 1996-06-07 | Pyrimidindion-, pyrimidintrion-, triazindion-, tetrahydrokinazolindionderivater som <alfa>1-adrenergiske reseptorantagonister |
Country Status (32)
Country | Link |
---|---|
EP (1) | EP0748800B1 (ru) |
JP (1) | JP2721147B2 (ru) |
KR (1) | KR100446877B1 (ru) |
CN (1) | CN1118459C (ru) |
AR (1) | AR003428A1 (ru) |
AT (1) | ATE201016T1 (ru) |
AU (1) | AU710754B2 (ru) |
BR (1) | BR9602705A (ru) |
CA (1) | CA2178548A1 (ru) |
CO (1) | CO4700472A1 (ru) |
CZ (1) | CZ290004B6 (ru) |
DE (1) | DE69612698T2 (ru) |
DK (1) | DK0748800T3 (ru) |
ES (1) | ES2157366T3 (ru) |
GR (1) | GR3036307T3 (ru) |
HK (1) | HK1013065A1 (ru) |
HU (1) | HU223594B1 (ru) |
IL (1) | IL118519A (ru) |
MA (1) | MA23899A1 (ru) |
MY (1) | MY113499A (ru) |
NO (1) | NO309424B1 (ru) |
NZ (1) | NZ286720A (ru) |
PE (1) | PE46497A1 (ru) |
PL (1) | PL188061B1 (ru) |
PT (1) | PT748800E (ru) |
RU (1) | RU2175322C2 (ru) |
SA (1) | SA96170263B1 (ru) |
SG (1) | SG45486A1 (ru) |
TR (1) | TR970073A2 (ru) |
TW (1) | TW340846B (ru) |
UY (1) | UY24257A1 (ru) |
ZA (1) | ZA964561B (ru) |
Families Citing this family (43)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6271234B1 (en) | 1997-08-01 | 2001-08-07 | Recordati S.A., Chemical And Pharmaceutical Company | 1,4-disubstituted piperazines |
DE69830045T2 (de) * | 1997-10-31 | 2006-01-12 | Daiichi Suntory Pharma Co., Ltd. | Arylpiperidinopropanol und Arylpiperazinopropanol Derivate und dieselbe ent- haltende Pharmazeutika |
US6083950A (en) * | 1997-11-13 | 2000-07-04 | Ranbaxy Laboratories Limited | 1-(4-arylpiperazin-1-yl)-ω-[n-(α,ω-dicarboximido)]-alka nes useful as uro-selective α1-adrenoceptor blockers |
DK0949250T3 (da) * | 1998-03-30 | 2006-08-28 | Hoffmann La Roche | Fremgangsmåde til fremstilling af alpha1L-adrenoceptorantagonister |
AU1979799A (en) * | 1998-07-21 | 2000-02-14 | Ranbaxy Laboratories Limited | Arylpiperazine derivatives useful as uro-selective alpha-1-adrenoceptor blockers |
BR9912318A (pt) * | 1998-07-21 | 2001-05-02 | Ranbaxy Lab Ltd | Compostos de 1- (4-arilpiperazin-1-il) -w- [n- (ol, w -dicarboximido) ] alcanos de utilidade como bloqueadores uro-seletivos de 1 - adrenoceptor. |
WO2000029386A1 (en) | 1998-11-12 | 2000-05-25 | Merck & Co., Inc. | Pyrimidinedione derivatives useful as alpha 1a adrenoceptor antagonists |
US6358959B1 (en) | 1999-01-26 | 2002-03-19 | Merck & Co., Inc. | Polyazanaphthalenone derivatives useful as alpha 1a adrenoceptor antagonists |
US6387909B1 (en) | 1999-07-30 | 2002-05-14 | Recordati S.A. Chemical And Pharmaceutical Company | Thienopyranecarboxamide derivatives |
US6306861B1 (en) | 1999-07-30 | 2001-10-23 | Recordati S.A. Chemical And Pharmaceutical Company | Thienopyrancecarboxamide derivatives |
GB2355457A (en) | 1999-09-30 | 2001-04-25 | Merck & Co Inc | Novel spirotricyclic substituted azacycloalkane derivatives useful as alpha 1a adrenoceptor antagonists |
GB2355456A (en) | 1999-09-30 | 2001-04-25 | Merck & Co Inc | Novel arylhydantoin derivatives useful as alpha 1a adrenoceptor antagonists |
GB2355264A (en) | 1999-09-30 | 2001-04-18 | Merck & Co Inc | Spirohydantoin derivatives useful as alpha 1a adrenoceptor antagonists |
GB2355263A (en) | 1999-09-30 | 2001-04-18 | Merck & Co Inc | Lactam and cyclic urea derivatives useful as alpha 1a adrenoceptor antagonists |
US6403594B1 (en) | 1999-10-18 | 2002-06-11 | Recordati, S.A. Chemical And Pharmaceutical Company | Benzopyran derivatives |
US6365591B1 (en) | 1999-10-18 | 2002-04-02 | Recordati, S.A., Chemical And Pharmacueticals Company | Isoxazolecarboxamide derivatives |
EP1255738B1 (en) | 2000-01-25 | 2012-03-07 | Neurocrine Biosciences, Inc. | Gonadotropin-releasing hormone receptor antagonists and methods relating thereto |
CZ20031698A3 (cs) * | 2000-11-30 | 2003-11-12 | Ranbaxy Laboratories Limited | 1,4-Disubstituované piperazinové deriváty využitelné jako uro-selektivní alfa1-adrenoreceptorové blokátory |
EP1414808A1 (en) | 2001-08-02 | 2004-05-06 | Neurocrine Biosciences, Inc. | 1,2,4-triazin-3,5-diones as gonadotropin-releasing hormone receptor (gnrh) antagonists |
DE10311065A1 (de) | 2003-03-13 | 2004-09-23 | Abbott Gmbh & Co. Kg | Pyrimidin-2-on-Verbindungen und ihre therapeutische Verwendung |
US7687625B2 (en) | 2003-03-25 | 2010-03-30 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
BRPI0413452A (pt) | 2003-08-13 | 2006-10-17 | Takeda Pharmaceutical | composto, composição farmacêutica, kit, artigo de fabricação, e, métodos de inibir dpp-iv, terapêutico e de tratar um estado de doença, cáncer, distúrbios autoimunes, uma condição einfecção por hiv |
US7790734B2 (en) | 2003-09-08 | 2010-09-07 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
MY140489A (en) * | 2003-12-26 | 2009-12-31 | Eisai R&D Man Co Ltd | 1,2-di (cyclic) substituted benzene compounds |
GB0400290D0 (en) | 2004-01-08 | 2004-02-11 | Medivir Ab | dUTPase inhibitors |
AU2004318013B8 (en) | 2004-03-15 | 2011-10-06 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
EP1655288A1 (en) * | 2004-11-05 | 2006-05-10 | Institut Pasteur | Aryl pyrimidyl compounds, pharmaceutical compositions comprising them, their use as antimicrobial agents |
KR101274879B1 (ko) | 2004-12-20 | 2013-06-14 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 1-시클로프로필메틸-4-[2-(3,3,5,5-테트라메틸시클로헥실)페닐]피페라진의 염 및 결정 |
EP2805953B1 (en) | 2004-12-21 | 2016-03-09 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
AU2006250388A1 (en) * | 2005-05-25 | 2006-11-30 | Eisai R & D Management Co., Ltd. | Intermediate in production of [2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine compound |
EP1942898B2 (en) | 2005-09-14 | 2014-05-14 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors for treating diabetes |
JP5122462B2 (ja) * | 2005-09-16 | 2013-01-16 | 武田薬品工業株式会社 | ジペプチジルペプチダーゼ阻害剤 |
US8324383B2 (en) | 2006-09-13 | 2012-12-04 | Takeda Pharmaceutical Company Limited | Methods of making polymorphs of benzoate salt of 2-[[6-[(3R)-3-amino-1-piperidinyl]-3,4-dihydro-3-methyl-2,4-dioxo-1(2H)-pyrimidinyl]methyl]-benzonitrile |
TW200838536A (en) | 2006-11-29 | 2008-10-01 | Takeda Pharmaceutical | Polymorphs of succinate salt of 2-[6-(3-amino-piperidin-1-yl)-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethy]-4-fluor-benzonitrile and methods of use therefor |
US8093236B2 (en) | 2007-03-13 | 2012-01-10 | Takeda Pharmaceuticals Company Limited | Weekly administration of dipeptidyl peptidase inhibitors |
DE102008030091B4 (de) * | 2008-06-25 | 2011-03-03 | Resprotect Gmbh | Uracilderivate und deren Verwendung |
US9452980B2 (en) | 2009-12-22 | 2016-09-27 | Hoffmann-La Roche Inc. | Substituted benzamides |
RU2449994C1 (ru) * | 2011-03-10 | 2012-05-10 | Светлана Алексеевна Мещерякова | 6-(4-бензилпиперазино)-1,3-диметилурацила дигидрохлорид, проявляющий биологическую активность |
MY161170A (en) * | 2011-03-18 | 2017-04-14 | Corcept Therapeutics Inc | Pyrimidine cyclohexyl glucocorticoid receptor modulators |
GB201318886D0 (en) * | 2013-10-25 | 2013-12-11 | Givaudan Sa | Improvements i or relating to organic compounds |
SG11201807516UA (en) | 2016-03-17 | 2018-09-27 | Hoffmann La Roche | 5-ethyl-4-methyl-pyrazole-3-carboxamide derivative having activity as agonist of taar |
CA3157658A1 (en) * | 2019-10-28 | 2021-05-06 | Nippon Soda Co., Ltd. | 2,6-dioxo-3,6-dihydropyrimidine compound, agricultural and horticultural bactericide, nematicide, and medical and veterinary antifungal agent |
US20240260575A1 (en) * | 2021-04-28 | 2024-08-08 | Nippon Soda Co., Ltd. | Agricultural and horticultural fungicidal composition |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2727469A1 (de) * | 1977-06-18 | 1978-12-21 | Hoechst Ag | Neue hexahydropyrimidine, verfahren zu ihrer herstellung und arzneimittel, die diese verbindungen enthalten |
JPH02184667A (ja) * | 1989-01-11 | 1990-07-19 | Meiji Seika Kaisha Ltd | N,n’―ジ置換ピペラジル誘導体及びそれを有効成分とする排尿障害改善剤 |
JPH0344379A (ja) * | 1989-07-13 | 1991-02-26 | Yamasa Shoyu Co Ltd | N↑3―ピペラジノウラシル誘導体 |
JP2814600B2 (ja) * | 1989-08-31 | 1998-10-22 | 正幸 石川 | 排尿障害治療剤 |
SG65570A1 (en) * | 1992-02-25 | 1999-06-22 | Recordati Chem Pharm | Heterobicyclic compounds |
FR2727682A1 (fr) * | 1994-12-02 | 1996-06-07 | Pf Medicament | Nouveaux derives de 3,5-dioxo-(2h,4h)-1,2,4-triazines, leur preparation et leur application a titre de medicament |
-
1996
- 1996-05-28 AT AT96108493T patent/ATE201016T1/de not_active IP Right Cessation
- 1996-05-28 DE DE69612698T patent/DE69612698T2/de not_active Expired - Fee Related
- 1996-05-28 DK DK96108493T patent/DK0748800T3/da active
- 1996-05-28 EP EP96108493A patent/EP0748800B1/en not_active Expired - Lifetime
- 1996-05-28 ES ES96108493T patent/ES2157366T3/es not_active Expired - Lifetime
- 1996-05-28 PT PT96108493T patent/PT748800E/pt unknown
- 1996-05-31 IL IL11851996A patent/IL118519A/xx not_active IP Right Cessation
- 1996-06-03 AU AU54690/96A patent/AU710754B2/en not_active Ceased
- 1996-06-03 ZA ZA964561A patent/ZA964561B/xx unknown
- 1996-06-04 NZ NZ286720A patent/NZ286720A/en unknown
- 1996-06-05 PL PL96314635A patent/PL188061B1/pl not_active IP Right Cessation
- 1996-06-05 HU HU9601529A patent/HU223594B1/hu not_active IP Right Cessation
- 1996-06-06 TR TR96/00475A patent/TR970073A2/xx unknown
- 1996-06-06 MA MA24270A patent/MA23899A1/fr unknown
- 1996-06-06 AR ARP960103000A patent/AR003428A1/es active IP Right Grant
- 1996-06-06 PE PE1996000428A patent/PE46497A1/es not_active Application Discontinuation
- 1996-06-07 NO NO962412A patent/NO309424B1/no unknown
- 1996-06-07 UY UY24257A patent/UY24257A1/es not_active IP Right Cessation
- 1996-06-07 JP JP8145236A patent/JP2721147B2/ja not_active Expired - Fee Related
- 1996-06-07 SG SG1996010018A patent/SG45486A1/en unknown
- 1996-06-07 MY MYPI96002314A patent/MY113499A/en unknown
- 1996-06-07 CN CN96110490A patent/CN1118459C/zh not_active Expired - Fee Related
- 1996-06-07 BR BR9602705A patent/BR9602705A/pt not_active IP Right Cessation
- 1996-06-07 RU RU96111418/04A patent/RU2175322C2/ru not_active IP Right Cessation
- 1996-06-07 CA CA002178548A patent/CA2178548A1/en not_active Abandoned
- 1996-06-07 CO CO96029677A patent/CO4700472A1/es unknown
- 1996-06-08 KR KR1019960020447A patent/KR100446877B1/ko not_active IP Right Cessation
- 1996-06-10 CZ CZ19961696A patent/CZ290004B6/cs not_active IP Right Cessation
- 1996-07-11 TW TW085108416A patent/TW340846B/zh active
- 1996-08-26 SA SA96170263A patent/SA96170263B1/ar unknown
-
1998
- 1998-12-21 HK HK98114167A patent/HK1013065A1/xx not_active IP Right Cessation
-
2001
- 2001-07-31 GR GR20010401157T patent/GR3036307T3/el not_active IP Right Cessation
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
NO309424B1 (no) | Pyrimidindion-, pyrimidintrion-, triazindion-, tetrahydrokinazolindionderivater som <alfa>1-adrenergiske reseptorantagonister | |
US5859014A (en) | Pyrimidinedione, pyrimidinetrione, triazinedione and tetrahydroquinazolinedione derivatives as α1 -adrenergic receptor antagonists | |
US5223505A (en) | Pyrimidine derivatives | |
RU2096411C1 (ru) | Производные бензимидазолона, смеси их изомеров или их кислотно-аддитивные соли в качестве антагониста рецептора 5-ht*00i*00a и 5-нт*002 | |
JPH0314563A (ja) | 新規4―フルオロ安息香酸誘導体 | |
JPH0794447B2 (ja) | キナゾリン誘導体 | |
RU2356896C2 (ru) | Производные хиназолина | |
NZ280396A (en) | Substituted piperazino derivatives, preparative process and medicaments | |
DK151017B (da) | Analogifremgangsmaade til fremstiiling af substituerede n-(4-indolyl-piperidino-alkyl)-benzimidazoloner eller fysiologisk acceptable syreadditionssalte deraf | |
CZ212594A3 (en) | Indole derivatives, process of their preparation, intermediates of such process, pharmaceutical compositions containing said derivatives and the use of the derivatives | |
AU2016319597A1 (en) | Novel benzimidazole compound and pharmaceutical use of same | |
US7582760B2 (en) | Benzimidazolone and dihydroindolone derivatives and uses thereof | |
NO178968B (no) | Analogifremgangsmåte for fremstilling av terapeutisk aktive aminopyrimidin-karboksamidderivater | |
US4950670A (en) | 6-phenyl-3-(piperazinyalalkyl)-2,4(1H,3H)-pyrimidinedione derivatives, their preparation and their application in therapy | |
US6355641B1 (en) | Oxazolone derivatives and uses thereof | |
EP0901473B1 (en) | Piperazinylalkylthiopyrimidine derivatives, pharmaceutical compositions containing the same and a process for the preparation of the novel compounds | |
KR870001168B1 (ko) | 이소인돌 유도체의 제조방법 | |
KR100917041B1 (ko) | 5-ht7 수용체에 길항작용을 갖는 신규한 화합물 | |
US7939520B2 (en) | Aminoazacyclyl-3-sulfonylindazoles as 5-hydroxytryptamine-6 ligands |