SK280901B6 - Piperidínové deriváty, spôsob ich výroby, farmaceutické prostriedky s ich obsahom a ich použitie - Google Patents

Info

Publication number

SK280901B6

SK280901B6 SK383-96A SK38396A SK280901B6 SK 280901 B6 SK280901 B6 SK 280901B6 SK 38396 A SK38396 A SK 38396A SK 280901 B6 SK280901 B6 SK 280901B6

Authority

SK

Slovakia

Prior art keywords

formula

methoxy

dichloromethane

tetrazol

compounds

Prior art date

1993-09-22

Links

• Espacenet
• Global Dossier
• Discuss

• 238000000034 method Methods 0.000 title claims abstract description 60
• 150000003053 piperidines Chemical class 0.000 title claims abstract description 29
• 239000003814 drug Substances 0.000 title claims description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 298
• 238000002360 preparation method Methods 0.000 claims abstract description 27
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
• 102000003141 Tachykinin Human genes 0.000 claims abstract description 8
• 108060008037 tachykinin Proteins 0.000 claims abstract description 8
• -1 2-methoxy-5-tetrazol-1-yl-benzyl Chemical group 0.000 claims description 85
• PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 36
• 150000003839 salts Chemical class 0.000 claims description 36
• 229910052739 hydrogen Inorganic materials 0.000 claims description 25
• 239000001257 hydrogen Substances 0.000 claims description 24
• 150000001412 amines Chemical class 0.000 claims description 22
• 239000012453 solvate Substances 0.000 claims description 18
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 16
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 13
• 239000004480 active ingredient Substances 0.000 claims description 13
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
• 125000004432 carbon atom Chemical group C* 0.000 claims description 10
• 125000000217 alkyl group Chemical group 0.000 claims description 9
• 150000002431 hydrogen Chemical class 0.000 claims description 9
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
• 125000005843 halogen group Chemical group 0.000 claims description 6
• 235000019270 ammonium chloride Nutrition 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 5
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
• 230000002829 reductive effect Effects 0.000 claims description 5
• 239000003638 chemical reducing agent Substances 0.000 claims description 4
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
• 230000001404 mediated effect Effects 0.000 claims description 3
• 239000003369 serotonin 5-HT3 receptor antagonist Substances 0.000 claims description 3
• FELGMEQIXOGIFQ-CYBMUJFWSA-N (3r)-9-methyl-3-[(2-methylimidazol-1-yl)methyl]-2,3-dihydro-1h-carbazol-4-one Chemical compound CC1=NC=CN1C[C@@H]1C(=O)C(C=2C(=CC=CC=2)N2C)=C2CC1 FELGMEQIXOGIFQ-CYBMUJFWSA-N 0.000 claims description 2
• 125000002252 acyl group Chemical group 0.000 claims description 2
• MFWNKCLOYSRHCJ-BTTYYORXSA-N granisetron Chemical compound C1=CC=C2C(C(=O)N[C@H]3C[C@H]4CCC[C@@H](C3)N4C)=NN(C)C2=C1 MFWNKCLOYSRHCJ-BTTYYORXSA-N 0.000 claims description 2
• 229960003727 granisetron Drugs 0.000 claims description 2
• 229910052736 halogen Inorganic materials 0.000 claims description 2
• 150000002367 halogens Chemical class 0.000 claims description 2
• 229910052751 metal Inorganic materials 0.000 claims description 2
• 239000002184 metal Substances 0.000 claims description 2
• TTWJBBZEZQICBI-UHFFFAOYSA-N metoclopramide Chemical compound CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OC TTWJBBZEZQICBI-UHFFFAOYSA-N 0.000 claims description 2
• 229960004503 metoclopramide Drugs 0.000 claims description 2
• 229960005343 ondansetron Drugs 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims 1
• UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
• 239000005557 antagonist Substances 0.000 abstract description 4
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 378
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 230
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 195
• 239000000243 solution Substances 0.000 description 143
• 239000000543 intermediate Substances 0.000 description 130
• 239000000203 mixture Substances 0.000 description 127
• 239000007787 solid Substances 0.000 description 115
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 114
• QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 109
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 97
• 235000019441 ethanol Nutrition 0.000 description 81
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 71
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 59
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 58
• 229910021529 ammonia Inorganic materials 0.000 description 53
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 52
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 45
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 41
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 38
• 239000002904 solvent Substances 0.000 description 37
• 229910052757 nitrogen Inorganic materials 0.000 description 35
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 31
• 239000007858 starting material Substances 0.000 description 31
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 26
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 26
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
• 229910052938 sodium sulfate Inorganic materials 0.000 description 24
• 235000011152 sodium sulphate Nutrition 0.000 description 24
• 239000003921 oil Substances 0.000 description 23
• 235000019198 oils Nutrition 0.000 description 23
• 229910000029 sodium carbonate Inorganic materials 0.000 description 22
• 239000011541 reaction mixture Substances 0.000 description 20
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 19
• 238000001704 evaporation Methods 0.000 description 19
• 230000008020 evaporation Effects 0.000 description 19
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 19
• 235000019341 magnesium sulphate Nutrition 0.000 description 19
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
• SJSWRKNSCWKNIR-UHFFFAOYSA-N azane;dihydrochloride Chemical compound N.Cl.Cl SJSWRKNSCWKNIR-UHFFFAOYSA-N 0.000 description 18
• 238000003818 flash chromatography Methods 0.000 description 18
• 239000003826 tablet Substances 0.000 description 18
• 238000006243 chemical reaction Methods 0.000 description 17
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 16
• 229960000583 acetic acid Drugs 0.000 description 16
• 239000000725 suspension Substances 0.000 description 16
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
• 238000003756 stirring Methods 0.000 description 15
• 239000000126 substance Substances 0.000 description 15
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
• 238000001035 drying Methods 0.000 description 14
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
• 239000000843 powder Substances 0.000 description 14
• 239000002775 capsule Substances 0.000 description 13
• 239000000284 extract Substances 0.000 description 13
• 206010047700 Vomiting Diseases 0.000 description 12
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 12
• 239000000047 product Substances 0.000 description 12
• 238000010992 reflux Methods 0.000 description 11
• LGWHVLLTRCDFDK-UHFFFAOYSA-N 2-methoxy-5-(5-methyltetrazol-1-yl)benzaldehyde Chemical compound C1=C(C=O)C(OC)=CC=C1N1C(C)=NN=N1 LGWHVLLTRCDFDK-UHFFFAOYSA-N 0.000 description 10
• PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 10
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
• 238000010521 absorption reaction Methods 0.000 description 10
• 239000002253 acid Substances 0.000 description 10
• QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 10
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
• WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 9
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
• 208000002193 Pain Diseases 0.000 description 9
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 9
• 239000003054 catalyst Substances 0.000 description 9
• 239000000460 chlorine Substances 0.000 description 9
• 238000001816 cooling Methods 0.000 description 9
• 239000000706 filtrate Substances 0.000 description 9
• 238000001914 filtration Methods 0.000 description 9
• 238000004452 microanalysis Methods 0.000 description 9
• PITHNUWDJUJELK-UHFFFAOYSA-N 2-methoxy-5-(tetrazol-1-yl)benzaldehyde Chemical compound C1=C(C=O)C(OC)=CC=C1N1N=NN=C1 PITHNUWDJUJELK-UHFFFAOYSA-N 0.000 description 8
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
• VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 8
• 239000007788 liquid Substances 0.000 description 8
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 7
• 239000002585 base Substances 0.000 description 7
• 238000004587 chromatography analysis Methods 0.000 description 7
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
• 239000012458 free base Substances 0.000 description 7
• 239000012362 glacial acetic acid Substances 0.000 description 7
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 7
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 7
• 229910000027 potassium carbonate Inorganic materials 0.000 description 7
• YQNRPEFJKQVSNX-UHFFFAOYSA-N 2-methoxy-5-[5-(trifluoromethyl)tetrazol-1-yl]benzaldehyde Chemical compound C1=C(C=O)C(OC)=CC=C1N1C(C(F)(F)F)=NN=N1 YQNRPEFJKQVSNX-UHFFFAOYSA-N 0.000 description 6
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 6
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 6
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 6
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
• HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
• UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 6
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
• 238000000605 extraction Methods 0.000 description 6
• 229910052731 fluorine Inorganic materials 0.000 description 6
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 6
• 239000010410 layer Substances 0.000 description 6
• 235000019359 magnesium stearate Nutrition 0.000 description 6
• NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 6
• UBSPKGKFFQKZJB-UHFFFAOYSA-N methyl 4-nitrobutanoate Chemical compound COC(=O)CCC[N+]([O-])=O UBSPKGKFFQKZJB-UHFFFAOYSA-N 0.000 description 6
• VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 6
• 239000000829 suppository Substances 0.000 description 6
• 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 6
• UUOLETYDNTVQDY-UHFFFAOYSA-N 2-chloro-3-nitropyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1Cl UUOLETYDNTVQDY-UHFFFAOYSA-N 0.000 description 5
• 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 5
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
• 238000005481 NMR spectroscopy Methods 0.000 description 5
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
• 239000007864 aqueous solution Substances 0.000 description 5
• 230000027455 binding Effects 0.000 description 5
• 229910052794 bromium Inorganic materials 0.000 description 5
• 229910052801 chlorine Inorganic materials 0.000 description 5
• 238000000354 decomposition reaction Methods 0.000 description 5
• 238000010511 deprotection reaction Methods 0.000 description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
• 239000011737 fluorine Substances 0.000 description 5
• 239000004615 ingredient Substances 0.000 description 5
• 239000000463 material Substances 0.000 description 5
• 239000012044 organic layer Substances 0.000 description 5
• 239000012321 sodium triacetoxyborohydride Substances 0.000 description 5
• 230000008673 vomiting Effects 0.000 description 5
• RDLGAKSDKYJGDS-UHFFFAOYSA-N 2-hydroxy-5-(tetrazol-1-yl)benzaldehyde Chemical compound C1=C(C=O)C(O)=CC=C1N1N=NN=C1 RDLGAKSDKYJGDS-UHFFFAOYSA-N 0.000 description 4
• GFMAFYNUQDLPBP-UHFFFAOYSA-N 2-phenylpiperidin-3-amine Chemical compound NC1CCCNC1C1=CC=CC=C1 GFMAFYNUQDLPBP-UHFFFAOYSA-N 0.000 description 4
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
• 229920003084 Avicel® PH-102 Polymers 0.000 description 4
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
• 206010019233 Headaches Diseases 0.000 description 4
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
• 235000011114 ammonium hydroxide Nutrition 0.000 description 4
• PXWLUICTRPHECG-UHFFFAOYSA-N azane;trihydrochloride Chemical compound N.Cl.Cl.Cl PXWLUICTRPHECG-UHFFFAOYSA-N 0.000 description 4
• 238000009903 catalytic hydrogenation reaction Methods 0.000 description 4
• 239000012043 crude product Substances 0.000 description 4
• 201000010099 disease Diseases 0.000 description 4
• IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 4
• 238000009472 formulation Methods 0.000 description 4
• 231100000869 headache Toxicity 0.000 description 4
• 210000004379 membrane Anatomy 0.000 description 4
• 239000012528 membrane Substances 0.000 description 4
• 229910052987 metal hydride Inorganic materials 0.000 description 4
• 150000004681 metal hydrides Chemical class 0.000 description 4
• 239000012299 nitrogen atmosphere Substances 0.000 description 4
• 239000000546 pharmaceutical excipient Substances 0.000 description 4
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
• 102000005962 receptors Human genes 0.000 description 4
• 108020003175 receptors Proteins 0.000 description 4
• 239000011347 resin Substances 0.000 description 4
• 229920005989 resin Polymers 0.000 description 4
• 239000000375 suspending agent Substances 0.000 description 4
• 238000012360 testing method Methods 0.000 description 4
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
• WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 4
• 238000001665 trituration Methods 0.000 description 4
• 239000008215 water for injection Substances 0.000 description 4
• CMIBUZBMZCBCAT-HZPDHXFCSA-N (2r,3r)-2,3-bis[(4-methylbenzoyl)oxy]butanedioic acid Chemical compound C1=CC(C)=CC=C1C(=O)O[C@@H](C(O)=O)[C@H](C(O)=O)OC(=O)C1=CC=C(C)C=C1 CMIBUZBMZCBCAT-HZPDHXFCSA-N 0.000 description 3
• NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 description 3
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
• USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 3
• 239000005695 Ammonium acetate Substances 0.000 description 3
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
• CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 3
• 235000019257 ammonium acetate Nutrition 0.000 description 3
• 229940043376 ammonium acetate Drugs 0.000 description 3
• 230000015572 biosynthetic process Effects 0.000 description 3
• 229910000085 borane Inorganic materials 0.000 description 3
• 201000011510 cancer Diseases 0.000 description 3
• 229910052799 carbon Inorganic materials 0.000 description 3
• 239000003795 chemical substances by application Substances 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
• 238000004440 column chromatography Methods 0.000 description 3
• 238000007796 conventional method Methods 0.000 description 3
• 239000013078 crystal Substances 0.000 description 3
• 238000002425 crystallisation Methods 0.000 description 3
• 230000008025 crystallization Effects 0.000 description 3
• 239000002270 dispersing agent Substances 0.000 description 3
• 238000002474 experimental method Methods 0.000 description 3
• 235000019197 fats Nutrition 0.000 description 3
• 238000001640 fractional crystallisation Methods 0.000 description 3
• 238000010438 heat treatment Methods 0.000 description 3
• 239000004312 hexamethylene tetramine Substances 0.000 description 3
• 235000010299 hexamethylene tetramine Nutrition 0.000 description 3
• 150000002466 imines Chemical class 0.000 description 3
• 238000000338 in vitro Methods 0.000 description 3
• 239000008101 lactose Substances 0.000 description 3
• 230000003287 optical effect Effects 0.000 description 3
• 229910052763 palladium Inorganic materials 0.000 description 3
• QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
• PEUGKEHLRUVPAN-UHFFFAOYSA-N piperidin-3-amine Chemical class NC1CCCNC1 PEUGKEHLRUVPAN-UHFFFAOYSA-N 0.000 description 3
• 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 3
• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
• 239000003755 preservative agent Substances 0.000 description 3
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
• 239000002002 slurry Substances 0.000 description 3
• 239000011734 sodium Substances 0.000 description 3
• 229910052708 sodium Inorganic materials 0.000 description 3
• 239000012279 sodium borohydride Substances 0.000 description 3
• 229910000033 sodium borohydride Inorganic materials 0.000 description 3
• 239000004317 sodium nitrate Substances 0.000 description 3
• 235000010344 sodium nitrate Nutrition 0.000 description 3
• 239000003381 stabilizer Substances 0.000 description 3
• 238000007920 subcutaneous administration Methods 0.000 description 3
• 229910052717 sulfur Inorganic materials 0.000 description 3
• 150000003536 tetrazoles Chemical class 0.000 description 3
• GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 3
• KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
• YJQDBKGGRPJSOI-UHFFFAOYSA-N (3-formyl-4-methoxyphenyl)boronic acid Chemical compound COC1=CC=C(B(O)O)C=C1C=O YJQDBKGGRPJSOI-UHFFFAOYSA-N 0.000 description 2
• PWMVXBCPDVMGTP-UHFFFAOYSA-N (3-formyl-4-methoxyphenyl)cyanamide Chemical compound COC1=CC=C(NC#N)C=C1C=O PWMVXBCPDVMGTP-UHFFFAOYSA-N 0.000 description 2
• FZHWJJRTEIUGMD-KOLCDFICSA-N (5r,6s)-6-(3-bromophenyl)-5-nitropiperidin-2-one Chemical compound [O-][N+](=O)[C@@H]1CCC(=O)N[C@H]1C1=CC=CC(Br)=C1 FZHWJJRTEIUGMD-KOLCDFICSA-N 0.000 description 2
• XTYXKLZQDSOFES-PWSUYJOCSA-N (5r,6s)-6-(4-methoxyphenyl)-5-nitropiperidin-2-one Chemical compound C1=CC(OC)=CC=C1[C@H]1[C@H]([N+]([O-])=O)CCC(=O)N1 XTYXKLZQDSOFES-PWSUYJOCSA-N 0.000 description 2
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
• SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
• OKFQMBUOPVEZKI-UHFFFAOYSA-N 1-(3-fluoro-4-phenylmethoxyphenyl)-5-methyltetrazole Chemical compound CC1=NN=NN1C(C=C1F)=CC=C1OCC1=CC=CC=C1 OKFQMBUOPVEZKI-UHFFFAOYSA-N 0.000 description 2
• PHMJZCMURONFOQ-UHFFFAOYSA-N 1-(4-phenylmethoxyphenyl)-5-(trifluoromethyl)tetrazole Chemical compound FC(F)(F)C1=NN=NN1C(C=C1)=CC=C1OCC1=CC=CC=C1 PHMJZCMURONFOQ-UHFFFAOYSA-N 0.000 description 2
• ZOENJPQKPLXOGE-UHFFFAOYSA-N 1-(cyclopropylmethyl)tetrazole Chemical compound C1=NN=NN1CC1CC1 ZOENJPQKPLXOGE-UHFFFAOYSA-N 0.000 description 2
• QVVBOTVSYCJUSQ-UHFFFAOYSA-N 1-[3-(1,3-dioxolan-2-yl)-4-methoxyphenyl]-5-methylsulfanyltetrazole Chemical compound COC1=CC=C(N2C(=NN=N2)SC)C=C1C1OCCO1 QVVBOTVSYCJUSQ-UHFFFAOYSA-N 0.000 description 2
• FSEIKIAFEPQJBM-UHFFFAOYSA-N 1-[3-(1,3-dioxolan-2-yl)-4-methoxyphenyl]tetrazol-5-amine Chemical compound COC1=CC=C(N2C(=NN=N2)N)C=C1C1OCCO1 FSEIKIAFEPQJBM-UHFFFAOYSA-N 0.000 description 2
• ZGEOYRPBZDERPR-UHFFFAOYSA-N 1-[3-(1,3-dioxolan-2-yl)-4-methoxyphenyl]tetrazole Chemical compound COC1=CC=C(N2N=NN=C2)C=C1C1OCCO1 ZGEOYRPBZDERPR-UHFFFAOYSA-N 0.000 description 2
• WFQDTOYDVUWQMS-UHFFFAOYSA-N 1-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1 WFQDTOYDVUWQMS-UHFFFAOYSA-N 0.000 description 2
• KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Chemical compound C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 2
• PBOFYVXABUFIMT-UHFFFAOYSA-N 2,2,2-trifluoro-n-(4-phenylmethoxyphenyl)ethanimidoyl chloride Chemical compound C1=CC(N=C(Cl)C(F)(F)F)=CC=C1OCC1=CC=CC=C1 PBOFYVXABUFIMT-UHFFFAOYSA-N 0.000 description 2
• NATSYHRCJNDGIA-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-3-nitropyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1C1=CC=C(F)C(F)=C1 NATSYHRCJNDGIA-UHFFFAOYSA-N 0.000 description 2
• FVSSIWUXRRPEPW-UHFFFAOYSA-N 2-(3-fluoro-4-methylphenyl)-3-nitropyridine Chemical compound C1=C(F)C(C)=CC=C1C1=NC=CC=C1[N+]([O-])=O FVSSIWUXRRPEPW-UHFFFAOYSA-N 0.000 description 2
• PXHJVNQZUHJEPS-UHFFFAOYSA-N 2-(3-fluorophenyl)-3-nitropyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1C1=CC=CC(F)=C1 PXHJVNQZUHJEPS-UHFFFAOYSA-N 0.000 description 2
• WOFJRVBRBNYZFI-UHFFFAOYSA-N 2-(4-fluorophenyl)-3-nitropyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1C1=CC=C(F)C=C1 WOFJRVBRBNYZFI-UHFFFAOYSA-N 0.000 description 2
• RQQJAMKQXWKJMY-UHFFFAOYSA-N 2-(4-methylphenyl)-3-nitropyridine Chemical compound C1=CC(C)=CC=C1C1=NC=CC=C1[N+]([O-])=O RQQJAMKQXWKJMY-UHFFFAOYSA-N 0.000 description 2
• NJLAQWFIXLFBKW-UHFFFAOYSA-N 2-(4-nitrophenyl)tetrazole Chemical compound C1=CC([N+](=O)[O-])=CC=C1N1N=NC=N1 NJLAQWFIXLFBKW-UHFFFAOYSA-N 0.000 description 2
• UYAUZYHFXZCGBH-UHFFFAOYSA-N 2-(cyclopropylmethyl)tetrazole Chemical compound N1=CN=NN1CC1CC1 UYAUZYHFXZCGBH-UHFFFAOYSA-N 0.000 description 2
• AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
• XVCGKPAZYGTQET-UHFFFAOYSA-N 2-hydroxy-5-(5-methyltetrazol-1-yl)benzaldehyde Chemical compound CC1=NN=NN1C1=CC=C(O)C(C=O)=C1 XVCGKPAZYGTQET-UHFFFAOYSA-N 0.000 description 2
• PMKUXKYBORWOLE-UHFFFAOYSA-N 2-hydroxy-5-(5-phenyltetrazol-1-yl)benzaldehyde Chemical compound C1=C(C=O)C(O)=CC=C1N1C(C=2C=CC=CC=2)=NN=N1 PMKUXKYBORWOLE-UHFFFAOYSA-N 0.000 description 2
• MNMFUOLBSGIHHW-UHFFFAOYSA-N 2-hydroxy-5-(5-propyltetrazol-1-yl)benzaldehyde Chemical compound CCCC1=NN=NN1C1=CC=C(O)C(C=O)=C1 MNMFUOLBSGIHHW-UHFFFAOYSA-N 0.000 description 2
• LDMWCTPAPBSAPI-UHFFFAOYSA-N 2-hydroxy-5-(tetrazol-2-yl)benzaldehyde Chemical compound C1=C(C=O)C(O)=CC=C1N1N=NC=N1 LDMWCTPAPBSAPI-UHFFFAOYSA-N 0.000 description 2
• HUZDUGOQWSFXGK-UHFFFAOYSA-N 2-hydroxy-5-[5-(trifluoromethyl)tetrazol-1-yl]benzaldehyde Chemical compound C1=C(C=O)C(O)=CC=C1N1C(C(F)(F)F)=NN=N1 HUZDUGOQWSFXGK-UHFFFAOYSA-N 0.000 description 2
• RRRANKAAMRHRNT-UHFFFAOYSA-N 2-methoxy-5-(1-methyltetrazol-5-yl)benzaldehyde Chemical compound C1=C(C=O)C(OC)=CC=C1C1=NN=NN1C RRRANKAAMRHRNT-UHFFFAOYSA-N 0.000 description 2
• VJYKDNKGQKIUSE-UHFFFAOYSA-N 2-methoxy-5-(2-methyltetrazol-5-yl)benzaldehyde Chemical compound C1=C(C=O)C(OC)=CC=C1C1=NN(C)N=N1 VJYKDNKGQKIUSE-UHFFFAOYSA-N 0.000 description 2
• VBEHKYGAZVEBIA-UHFFFAOYSA-N 2-methoxy-5-(2h-tetrazol-5-yl)benzaldehyde Chemical compound C1=C(C=O)C(OC)=CC=C1C1=NN=NN1 VBEHKYGAZVEBIA-UHFFFAOYSA-N 0.000 description 2
• YEZGKPPNYNFRNK-UHFFFAOYSA-N 2-methoxy-5-(5-methylsulfanyltetrazol-1-yl)benzaldehyde Chemical compound C1=C(C=O)C(OC)=CC=C1N1C(SC)=NN=N1 YEZGKPPNYNFRNK-UHFFFAOYSA-N 0.000 description 2
• CLCRZYKTNHZYKS-UHFFFAOYSA-N 2-methoxy-5-(5-methylsulfonyltetrazol-1-yl)benzaldehyde Chemical compound C1=C(C=O)C(OC)=CC=C1N1C(S(C)(=O)=O)=NN=N1 CLCRZYKTNHZYKS-UHFFFAOYSA-N 0.000 description 2
• SFIFGMJFJJWWSY-UHFFFAOYSA-N 2-methoxy-5-(5-phenyltetrazol-1-yl)benzaldehyde Chemical compound C1=C(C=O)C(OC)=CC=C1N1C(C=2C=CC=CC=2)=NN=N1 SFIFGMJFJJWWSY-UHFFFAOYSA-N 0.000 description 2
• ADAQJXCXQIWYLW-UHFFFAOYSA-N 2-methoxy-5-(5-propyltetrazol-1-yl)benzaldehyde Chemical compound CCCC1=NN=NN1C1=CC=C(OC)C(C=O)=C1 ADAQJXCXQIWYLW-UHFFFAOYSA-N 0.000 description 2
• BYYVHDGSSPZEAN-UHFFFAOYSA-N 2-methoxy-5-(tetrazol-1-ylmethyl)benzaldehyde Chemical compound C1=C(C=O)C(OC)=CC=C1CN1N=NN=C1 BYYVHDGSSPZEAN-UHFFFAOYSA-N 0.000 description 2
• BQLVODDCLKODKL-UHFFFAOYSA-N 2-methoxy-5-(tetrazol-2-yl)benzaldehyde Chemical compound C1=C(C=O)C(OC)=CC=C1N1N=NC=N1 BQLVODDCLKODKL-UHFFFAOYSA-N 0.000 description 2
• YGQZWFYEBCZSAI-UHFFFAOYSA-N 2-methoxy-5-(tetrazol-2-ylmethyl)benzaldehyde Chemical compound C1=C(C=O)C(OC)=CC=C1CN1N=NC=N1 YGQZWFYEBCZSAI-UHFFFAOYSA-N 0.000 description 2
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
• ABONMZLRXQTGAL-UHFFFAOYSA-N 3-fluoro-2-hydroxy-5-(5-methyltetrazol-1-yl)benzaldehyde Chemical compound CC1=NN=NN1C1=CC(F)=C(O)C(C=O)=C1 ABONMZLRXQTGAL-UHFFFAOYSA-N 0.000 description 2
• DLLRQHPHTKZQLZ-UHFFFAOYSA-N 3-fluoro-2-methoxy-5-(5-methyltetrazol-1-yl)benzaldehyde Chemical compound C1=C(C=O)C(OC)=C(F)C=C1N1C(C)=NN=N1 DLLRQHPHTKZQLZ-UHFFFAOYSA-N 0.000 description 2
• GTJUICHDQGZVSX-UHFFFAOYSA-N 4-(4-methylbenzoyl)peroxy-4-oxobutanoic acid Chemical compound CC1=CC=C(C(=O)OOC(=O)CCC(O)=O)C=C1 GTJUICHDQGZVSX-UHFFFAOYSA-N 0.000 description 2
• LXKJBKXZXYCLSP-UHFFFAOYSA-N 4-(5-cyclopropyltetrazol-1-yl)phenol Chemical compound C1=CC(O)=CC=C1N1C(C2CC2)=NN=N1 LXKJBKXZXYCLSP-UHFFFAOYSA-N 0.000 description 2
• ALAWBLGYKHSCEU-UHFFFAOYSA-N 4-(5-ethyltetrazol-1-yl)phenol Chemical compound CCC1=NN=NN1C1=CC=C(O)C=C1 ALAWBLGYKHSCEU-UHFFFAOYSA-N 0.000 description 2
• GYQZGPBQMWZVLQ-UHFFFAOYSA-N 4-(5-methyltetrazol-1-yl)phenol Chemical compound CC1=NN=NN1C1=CC=C(O)C=C1 GYQZGPBQMWZVLQ-UHFFFAOYSA-N 0.000 description 2
• PQGLYPKJONLLFZ-UHFFFAOYSA-N 4-(5-phenyltetrazol-1-yl)phenol Chemical compound C1=CC(O)=CC=C1N1C(C=2C=CC=CC=2)=NN=N1 PQGLYPKJONLLFZ-UHFFFAOYSA-N 0.000 description 2
• AXJKWXIVFCNRCQ-UHFFFAOYSA-N 4-(tetrazol-1-yl)phenol Chemical compound C1=CC(O)=CC=C1N1N=NN=C1 AXJKWXIVFCNRCQ-UHFFFAOYSA-N 0.000 description 2
• HELCKJWIYMGRIB-UHFFFAOYSA-N 4-(tetrazol-2-yl)aniline Chemical compound C1=CC(N)=CC=C1N1N=NC=N1 HELCKJWIYMGRIB-UHFFFAOYSA-N 0.000 description 2
• XWEZECGCHUPQKW-UHFFFAOYSA-N 4-(tetrazol-2-yl)phenol Chemical compound C1=CC(O)=CC=C1N1N=NC=N1 XWEZECGCHUPQKW-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
• UOYXRXIWIBKGOM-UHFFFAOYSA-N 4-[5-(trifluoromethyl)tetrazol-1-yl]phenol Chemical compound C1=CC(O)=CC=C1N1C(C(F)(F)F)=NN=N1 UOYXRXIWIBKGOM-UHFFFAOYSA-N 0.000 description 2
• XSJYQLAPUDCMNM-UHFFFAOYSA-N 5-(1-ethyltetrazol-5-yl)-2-methoxybenzaldehyde Chemical compound CCN1N=NN=C1C1=CC=C(OC)C(C=O)=C1 XSJYQLAPUDCMNM-UHFFFAOYSA-N 0.000 description 2
• OZEVSTJDURDJOF-UHFFFAOYSA-N 5-(5-cyclopropyltetrazol-1-yl)-2-hydroxybenzaldehyde Chemical compound C1=C(C=O)C(O)=CC=C1N1C(C2CC2)=NN=N1 OZEVSTJDURDJOF-UHFFFAOYSA-N 0.000 description 2
• BESKRBMEPBFSIT-UHFFFAOYSA-N 5-(5-ethyltetrazol-1-yl)-2-methoxybenzaldehyde Chemical compound CCC1=NN=NN1C1=CC=C(OC)C(C=O)=C1 BESKRBMEPBFSIT-UHFFFAOYSA-N 0.000 description 2
• VLRPYFOEJAVUFG-UHFFFAOYSA-N 5-[1-(cyclopropylmethyl)tetrazol-5-yl]-2-methoxybenzaldehyde Chemical compound C1=C(C=O)C(OC)=CC=C1C1=NN=NN1CC1CC1 VLRPYFOEJAVUFG-UHFFFAOYSA-N 0.000 description 2
• FFSSSYQCLNKPPT-UHFFFAOYSA-N 5-[5-(diethylamino)tetrazol-1-yl]-2-methoxybenzaldehyde Chemical compound CCN(CC)C1=NN=NN1C1=CC=C(OC)C(C=O)=C1 FFSSSYQCLNKPPT-UHFFFAOYSA-N 0.000 description 2
• ITWKUABLTLRHAO-UHFFFAOYSA-N 5-[5-(dimethylamino)tetrazol-1-yl]-2-methoxybenzaldehyde Chemical compound C1=C(C=O)C(OC)=CC=C1N1C(N(C)C)=NN=N1 ITWKUABLTLRHAO-UHFFFAOYSA-N 0.000 description 2
• MBOQPWSBMDNBDD-UHFFFAOYSA-N 5-bromo-1-(cyclopropylmethyl)tetrazole Chemical compound BrC1=NN=NN1CC1CC1 MBOQPWSBMDNBDD-UHFFFAOYSA-N 0.000 description 2
• IJIBRSFAXRFPPN-UHFFFAOYSA-N 5-bromo-2-methoxybenzaldehyde Chemical compound COC1=CC=C(Br)C=C1C=O IJIBRSFAXRFPPN-UHFFFAOYSA-N 0.000 description 2
• ZJRZRSRWOWMNHE-UHFFFAOYSA-N 5-cyclopropyl-1-(4-phenylmethoxyphenyl)tetrazole Chemical compound C=1C=CC=CC=1COC(C=C1)=CC=C1N1N=NN=C1C1CC1 ZJRZRSRWOWMNHE-UHFFFAOYSA-N 0.000 description 2
• NEAOORGDJCBWDL-UHFFFAOYSA-N 5-hydroxyimino-6-(4-methoxyphenyl)piperidin-2-one Chemical compound C1=CC(OC)=CC=C1C1C(=NO)CCC(=O)N1 NEAOORGDJCBWDL-UHFFFAOYSA-N 0.000 description 2
• TWGZHFRZGBWJGX-UHFFFAOYSA-N 5-hydroxyimino-6-[4-(trifluoromethyl)phenyl]piperidin-2-one Chemical compound ON=C1CCC(=O)NC1C1=CC=C(C(F)(F)F)C=C1 TWGZHFRZGBWJGX-UHFFFAOYSA-N 0.000 description 2
• ZMPDDLKERLVLHI-UHFFFAOYSA-N 6-(3-bromo-4-methylphenyl)-5-hydroxyiminopiperidin-2-one Chemical compound C1=C(Br)C(C)=CC=C1C1C(=NO)CCC(=O)N1 ZMPDDLKERLVLHI-UHFFFAOYSA-N 0.000 description 2
• QONQTHCHUWXHBZ-UHFFFAOYSA-N 6-(3-bromo-4-methylphenyl)piperidine-2,5-dione Chemical compound C1=C(Br)C(C)=CC=C1C1C(=O)CCC(=O)N1 QONQTHCHUWXHBZ-UHFFFAOYSA-N 0.000 description 2
• YNRWWYKVAHHVGF-UHFFFAOYSA-N 6-(3-bromophenyl)-5-hydroxyiminopiperidin-2-one Chemical compound ON=C1CCC(=O)NC1C1=CC=CC(Br)=C1 YNRWWYKVAHHVGF-UHFFFAOYSA-N 0.000 description 2
• UGNQIOIMMKKDEC-UHFFFAOYSA-N 6-(3-bromophenyl)piperidine-2,5-dione Chemical compound BrC1=CC=CC(C2C(CCC(=O)N2)=O)=C1 UGNQIOIMMKKDEC-UHFFFAOYSA-N 0.000 description 2
• YVEKLBOLDXKKSU-UHFFFAOYSA-N 6-(3-chlorophenyl)-5-hydroxyiminopiperidin-2-one Chemical compound ON=C1CCC(=O)NC1C1=CC=CC(Cl)=C1 YVEKLBOLDXKKSU-UHFFFAOYSA-N 0.000 description 2
• KUSDAAUSAZOEDD-UHFFFAOYSA-N 6-(3-chlorophenyl)-5-nitropiperidin-2-one Chemical compound [O-][N+](=O)C1CCC(=O)NC1C1=CC=CC(Cl)=C1 KUSDAAUSAZOEDD-UHFFFAOYSA-N 0.000 description 2
• XUWAPPWBVIKXJS-UHFFFAOYSA-N 6-(3-chlorophenyl)piperidine-2,5-dione Chemical compound ClC1=CC=CC(C2C(CCC(=O)N2)=O)=C1 XUWAPPWBVIKXJS-UHFFFAOYSA-N 0.000 description 2
• QSIXZRWGOIPIGR-UHFFFAOYSA-N 6-(4-methoxyphenyl)piperidine-2,5-dione Chemical compound C1=CC(OC)=CC=C1C1C(=O)CCC(=O)N1 QSIXZRWGOIPIGR-UHFFFAOYSA-N 0.000 description 2
• ZZAAXHUOCIAQCI-UHFFFAOYSA-N 6-[4-(trifluoromethyl)phenyl]piperidine-2,5-dione Chemical compound C1=CC(C(F)(F)F)=CC=C1C1C(=O)CCC(=O)N1 ZZAAXHUOCIAQCI-UHFFFAOYSA-N 0.000 description 2
• 208000030507 AIDS Diseases 0.000 description 2
• 206010002383 Angina Pectoris Diseases 0.000 description 2
• 208000006820 Arthralgia Diseases 0.000 description 2
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
• 206010012289 Dementia Diseases 0.000 description 2
• 208000032131 Diabetic Neuropathies Diseases 0.000 description 2
• AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 2
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
• 239000012448 Lithium borohydride Substances 0.000 description 2
• 208000019695 Migraine disease Diseases 0.000 description 2
• 208000000112 Myalgia Diseases 0.000 description 2
• NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 description 2
• 206010028813 Nausea Diseases 0.000 description 2
• 239000002202 Polyethylene glycol Substances 0.000 description 2
• 208000003251 Pruritus Diseases 0.000 description 2
• 201000004681 Psoriasis Diseases 0.000 description 2
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
• OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 2
• PQNWGZHIYGTORX-UHFFFAOYSA-N [2-(1,3-dioxolan-2-yl)-4-methoxyphenyl]cyanamide Chemical compound COC1=CC=C(NC#N)C(C2OCCO2)=C1 PQNWGZHIYGTORX-UHFFFAOYSA-N 0.000 description 2
• NNWLFMQCSCIQEA-UHFFFAOYSA-N [2-methoxy-5-(tetrazol-1-yl)phenyl]methanol Chemical compound C1=C(CO)C(OC)=CC=C1N1N=NN=C1 NNWLFMQCSCIQEA-UHFFFAOYSA-N 0.000 description 2
• 230000002378 acidificating effect Effects 0.000 description 2
• RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 description 2
• 150000001299 aldehydes Chemical class 0.000 description 2
• 239000002168 alkylating agent Substances 0.000 description 2
• 229940100198 alkylating agent Drugs 0.000 description 2
• 229960004050 aminobenzoic acid Drugs 0.000 description 2
• 230000003042 antagnostic effect Effects 0.000 description 2
• 239000008346 aqueous phase Substances 0.000 description 2
• 230000037396 body weight Effects 0.000 description 2
• 210000004027 cell Anatomy 0.000 description 2
• 210000000170 cell membrane Anatomy 0.000 description 2
• 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
• DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 2
• 229960004316 cisplatin Drugs 0.000 description 2
• 238000003776 cleavage reaction Methods 0.000 description 2
• 239000003086 colorant Substances 0.000 description 2
• 239000012230 colorless oil Substances 0.000 description 2
• 238000006482 condensation reaction Methods 0.000 description 2
• 239000006071 cream Substances 0.000 description 2
• ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 2
• KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 2
• 210000002249 digestive system Anatomy 0.000 description 2
• 238000007907 direct compression Methods 0.000 description 2
• 208000035475 disorder Diseases 0.000 description 2
• 230000000694 effects Effects 0.000 description 2
• 239000003995 emulsifying agent Substances 0.000 description 2
• 239000000839 emulsion Substances 0.000 description 2
• 150000002148 esters Chemical class 0.000 description 2
• 238000011049 filling Methods 0.000 description 2
• 125000001153 fluoro group Chemical group F* 0.000 description 2
• 239000000499 gel Substances 0.000 description 2
• 239000007903 gelatin capsule Substances 0.000 description 2
• 239000008187 granular material Substances 0.000 description 2
• LIAWOTKNAVAKCX-UHFFFAOYSA-N hydrazine;dihydrochloride Chemical compound Cl.Cl.NN LIAWOTKNAVAKCX-UHFFFAOYSA-N 0.000 description 2
• 239000005457 ice water Substances 0.000 description 2
• 238000001727 in vivo Methods 0.000 description 2
• 238000002347 injection Methods 0.000 description 2
• 239000007924 injection Substances 0.000 description 2
• 238000007917 intracranial administration Methods 0.000 description 2
• HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
• 238000002955 isolation Methods 0.000 description 2
• JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropyl acetate Chemical compound CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 2
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
• 238000004811 liquid chromatography Methods 0.000 description 2
• RNQMFGYSBDLVRC-UHFFFAOYSA-N methyl 2-methoxy-5-(tetrazol-1-yl)benzoate Chemical compound C1=C(OC)C(C(=O)OC)=CC(N2N=NN=C2)=C1 RNQMFGYSBDLVRC-UHFFFAOYSA-N 0.000 description 2
• 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 2
• LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
• 206010027599 migraine Diseases 0.000 description 2
• BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
• 208000013465 muscle pain Diseases 0.000 description 2
• APHSYPVEGXYNKI-UHFFFAOYSA-N n-(4-phenylmethoxyphenyl)cyclopropanecarboxamide Chemical compound C1CC1C(=O)NC(C=C1)=CC=C1OCC1=CC=CC=C1 APHSYPVEGXYNKI-UHFFFAOYSA-N 0.000 description 2
• 230000008693 nausea Effects 0.000 description 2
• 208000004296 neuralgia Diseases 0.000 description 2
• 230000009871 nonspecific binding Effects 0.000 description 2
• 210000001331 nose Anatomy 0.000 description 2
• 239000002674 ointment Substances 0.000 description 2
• MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
• WYWIFABBXFUGLM-UHFFFAOYSA-N oxymetazoline Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C)=C1CC1=NCCN1 WYWIFABBXFUGLM-UHFFFAOYSA-N 0.000 description 2
• ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
• 238000007911 parenteral administration Methods 0.000 description 2
• 208000033808 peripheral neuropathy Diseases 0.000 description 2
• 239000003208 petroleum Substances 0.000 description 2
• 239000008363 phosphate buffer Substances 0.000 description 2
• 229910052697 platinum Inorganic materials 0.000 description 2
• 229910003446 platinum oxide Inorganic materials 0.000 description 2
• 229920000728 polyester Polymers 0.000 description 2
• 229920001223 polyethylene glycol Polymers 0.000 description 2
• 229920000642 polymer Polymers 0.000 description 2
• 229920002635 polyurethane Polymers 0.000 description 2
• 239000004814 polyurethane Substances 0.000 description 2
• 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
• 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
• 239000002244 precipitate Substances 0.000 description 2
• 102000004169 proteins and genes Human genes 0.000 description 2
• 108090000623 proteins and genes Proteins 0.000 description 2
• 238000000746 purification Methods 0.000 description 2
• 239000008213 purified water Substances 0.000 description 2
• 229940044551 receptor antagonist Drugs 0.000 description 2
• 239000002464 receptor antagonist Substances 0.000 description 2
• 230000007017 scission Effects 0.000 description 2
• 238000007789 sealing Methods 0.000 description 2
• 238000000926 separation method Methods 0.000 description 2
• 239000000377 silicon dioxide Substances 0.000 description 2
• GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
• 239000006188 syrup Substances 0.000 description 2
• 235000020357 syrup Nutrition 0.000 description 2
• HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 2
• 239000002562 thickening agent Substances 0.000 description 2
• 238000011200 topical administration Methods 0.000 description 2
• AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 2
• NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 2
• 239000003981 vehicle Substances 0.000 description 2
• 238000005550 wet granulation Methods 0.000 description 2
• DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 2
• CSLJQEHNSBDUMU-HZPDHXFCSA-N (2R,3R)-2,3-bis(4-methylbenzoyl)butanedioic acid Chemical compound Cc1ccc(cc1)C(=O)[C@@H]([C@@H](C(O)=O)C(=O)c1ccc(C)cc1)C(O)=O CSLJQEHNSBDUMU-HZPDHXFCSA-N 0.000 description 1
• OEYIMGVSEMSCIY-QZTJIDSGSA-N (2r,3r)-2,3-bis[(4-methylphenyl)methoxy]butanedioic acid Chemical compound C1=CC(C)=CC=C1CO[C@@H](C(O)=O)[C@H](C(O)=O)OCC1=CC=C(C)C=C1 OEYIMGVSEMSCIY-QZTJIDSGSA-N 0.000 description 1
• DTQNEFOKTXXQKV-HKUYNNGSSA-N (2s,3s)-n-[(2-methoxyphenyl)methyl]-2-phenylpiperidin-3-amine Chemical compound COC1=CC=CC=C1CN[C@@H]1[C@H](C=2C=CC=CC=2)NCCC1 DTQNEFOKTXXQKV-HKUYNNGSSA-N 0.000 description 1
• YVNRXILPJNISEM-FFUVTKDNSA-N (2s,3s)-n-[[2-methoxy-5-[5-(trifluoromethyl)tetrazol-1-yl]phenyl]methyl]-2-phenylpiperidin-3-amine;dihydrochloride Chemical compound Cl.Cl.C1([C@@H]2NCCC[C@@H]2NCC2=CC(=CC=C2OC)N2C(=NN=N2)C(F)(F)F)=CC=CC=C1 YVNRXILPJNISEM-FFUVTKDNSA-N 0.000 description 1
• UJTIPVXREXIGKW-VVJLZRNGSA-N (2s,3s)-n-[[5-(5-ethyltetrazol-1-yl)-2-methoxyphenyl]methyl]-2-phenylpiperidin-3-amine;dihydrochloride Chemical compound Cl.Cl.CCC1=NN=NN1C1=CC=C(OC)C(CN[C@@H]2[C@@H](NCCC2)C=2C=CC=CC=2)=C1 UJTIPVXREXIGKW-VVJLZRNGSA-N 0.000 description 1
• MVWAWWOKSVNOJG-UHFFFAOYSA-N (3,4-difluorophenoxy)boronic acid Chemical compound OB(O)OC1=CC=C(F)C(F)=C1 MVWAWWOKSVNOJG-UHFFFAOYSA-N 0.000 description 1
• RMGYQBHKEWWTOY-UHFFFAOYSA-N (3,4-difluorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(F)C(F)=C1 RMGYQBHKEWWTOY-UHFFFAOYSA-N 0.000 description 1
• WPVBHUUZDFUIJA-UHFFFAOYSA-N (3-fluoro-4-methylphenyl)boronic acid Chemical compound CC1=CC=C(B(O)O)C=C1F WPVBHUUZDFUIJA-UHFFFAOYSA-N 0.000 description 1
• KNXQDJCZSVHEIW-UHFFFAOYSA-N (3-fluorophenyl)boronic acid Chemical compound OB(O)C1=CC=CC(F)=C1 KNXQDJCZSVHEIW-UHFFFAOYSA-N 0.000 description 1
• DQVXWCCLFKMJTQ-UHFFFAOYSA-N (4-methylphenoxy)boronic acid Chemical compound CC1=CC=C(OB(O)O)C=C1 DQVXWCCLFKMJTQ-UHFFFAOYSA-N 0.000 description 1
• KQBDLOVXZHOAJI-UHFFFAOYSA-N (4-phenylmethoxyphenyl)azanium;chloride Chemical compound Cl.C1=CC(N)=CC=C1OCC1=CC=CC=C1 KQBDLOVXZHOAJI-UHFFFAOYSA-N 0.000 description 1
• LJCIZWPTTFFJTB-KOLCDFICSA-N (5r,6s)-5-nitro-6-[4-(trifluoromethyl)phenyl]piperidin-2-one Chemical compound [O-][N+](=O)[C@@H]1CCC(=O)N[C@H]1C1=CC=C(C(F)(F)F)C=C1 LJCIZWPTTFFJTB-KOLCDFICSA-N 0.000 description 1
• YPLUMYCVGMWPHW-PWSUYJOCSA-N (5r,6s)-6-(3-bromo-4-methylphenyl)-5-nitropiperidin-2-one Chemical compound C1=C(Br)C(C)=CC=C1[C@H]1[C@H]([N+]([O-])=O)CCC(=O)N1 YPLUMYCVGMWPHW-PWSUYJOCSA-N 0.000 description 1
• FDKXTQMXEQVLRF-ZHACJKMWSA-N (E)-dacarbazine Chemical compound CN(C)\N=N\c1[nH]cnc1C(N)=O FDKXTQMXEQVLRF-ZHACJKMWSA-N 0.000 description 1
• FGWYWKIOMUZSQF-UHFFFAOYSA-N 1,1,1-triethoxypropane Chemical compound CCOC(CC)(OCC)OCC FGWYWKIOMUZSQF-UHFFFAOYSA-N 0.000 description 1
• JAFMOTJMRSZOJE-UHFFFAOYSA-N 1,1,1-trimethoxybutane Chemical compound CCCC(OC)(OC)OC JAFMOTJMRSZOJE-UHFFFAOYSA-N 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
• MOXZSKYLLSPATM-UHFFFAOYSA-N 1-(4-hydroxyphenyl)-2h-tetrazole-5-thione Chemical compound C1=CC(O)=CC=C1N1C(=S)N=NN1 MOXZSKYLLSPATM-UHFFFAOYSA-N 0.000 description 1
• NKTWDHWKSWQFLS-UHFFFAOYSA-N 1-[3-(1,3-dioxolan-2-yl)-4-methoxyphenyl]-5-methyltetrazole Chemical compound COC1=CC=C(N2C(=NN=N2)C)C=C1C1OCCO1 NKTWDHWKSWQFLS-UHFFFAOYSA-N 0.000 description 1
• IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
• 238000005160 1H NMR spectroscopy Methods 0.000 description 1
• SINBGNJPYWNUQI-UHFFFAOYSA-N 2,2,2-trifluoro-1-imidazol-1-ylethanone Chemical compound FC(F)(F)C(=O)N1C=CN=C1 SINBGNJPYWNUQI-UHFFFAOYSA-N 0.000 description 1
• NRKYWOKHZRQRJR-UHFFFAOYSA-N 2,2,2-trifluoroacetamide Chemical compound NC(=O)C(F)(F)F NRKYWOKHZRQRJR-UHFFFAOYSA-N 0.000 description 1
• RQPTWBAIQNCYPL-UHFFFAOYSA-N 2-(4-anilinophenyl)acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1NC1=CC=CC=C1 RQPTWBAIQNCYPL-UHFFFAOYSA-N 0.000 description 1
• RFWYLXGEHPBJHF-UHFFFAOYSA-N 2-(4-fluorophenyl)piperidin-3-amine Chemical compound NC1CCCNC1C1=CC=C(F)C=C1 RFWYLXGEHPBJHF-UHFFFAOYSA-N 0.000 description 1
• RPMPQNRTPBUGIW-UHFFFAOYSA-N 2-(4-methylphenyl)piperidine Chemical compound C1=CC(C)=CC=C1C1NCCCC1 RPMPQNRTPBUGIW-UHFFFAOYSA-N 0.000 description 1
• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
• PVPHLBRYORUEBF-UHFFFAOYSA-N 2-ethoxy-5-(tetrazol-1-yl)benzaldehyde Chemical compound C1=C(C=O)C(OCC)=CC=C1N1N=NN=C1 PVPHLBRYORUEBF-UHFFFAOYSA-N 0.000 description 1
• QPFZIKLBJMQIOE-UHFFFAOYSA-N 2-fluoro-4-(5-methyltetrazol-1-yl)phenol Chemical compound CC1=NN=NN1C1=CC=C(O)C(F)=C1 QPFZIKLBJMQIOE-UHFFFAOYSA-N 0.000 description 1
• VNKLAQDBLDONTM-UHFFFAOYSA-N 2-hydroxy-5-(5-methylsulfanyltetrazol-1-yl)benzaldehyde Chemical compound CSC1=NN=NN1C1=CC=C(O)C(C=O)=C1 VNKLAQDBLDONTM-UHFFFAOYSA-N 0.000 description 1
• GRMRCJPFLWKJIU-UHFFFAOYSA-N 2-methoxy-5-[5-(3,3,3-trifluoro-2-oxopropyl)tetrazol-1-yl]benzaldehyde Chemical compound C1=C(C=O)C(OC)=CC=C1N1C(CC(=O)C(F)(F)F)=NN=N1 GRMRCJPFLWKJIU-UHFFFAOYSA-N 0.000 description 1
• REIWJVYUIKHROP-UHFFFAOYSA-N 2-methoxy-5-[5-(methylamino)tetrazol-1-yl]benzaldehyde Chemical compound C1=C(C=O)C(OC)=CC=C1N1C(=NC)NN=N1 REIWJVYUIKHROP-UHFFFAOYSA-N 0.000 description 1
• CDXWVKFXOLZNPJ-UHFFFAOYSA-N 2-propan-2-yl-5-(tetrazol-1-yl)benzaldehyde Chemical compound C1=C(C=O)C(C(C)C)=CC=C1N1N=NN=C1 CDXWVKFXOLZNPJ-UHFFFAOYSA-N 0.000 description 1
• BYBSGJORXJCKRA-UHFFFAOYSA-N 2-propan-2-yloxy-5-(tetrazol-1-yl)benzaldehyde Chemical compound C1=C(C=O)C(OC(C)C)=CC=C1N1N=NN=C1 BYBSGJORXJCKRA-UHFFFAOYSA-N 0.000 description 1
• RSVBUFKKJGQJMB-UHFFFAOYSA-N 3-(1,3-dioxolan-2-yl)-4-methoxybenzonitrile Chemical compound COC1=CC=C(C#N)C=C1C1OCCO1 RSVBUFKKJGQJMB-UHFFFAOYSA-N 0.000 description 1
• WTXXUAHMTVAQHW-UHFFFAOYSA-N 3-bromo-4-methylbenzaldehyde Chemical compound CC1=CC=C(C=O)C=C1Br WTXXUAHMTVAQHW-UHFFFAOYSA-N 0.000 description 1
• SUISZCALMBHJQX-UHFFFAOYSA-N 3-bromobenzaldehyde Chemical compound BrC1=CC=CC(C=O)=C1 SUISZCALMBHJQX-UHFFFAOYSA-N 0.000 description 1
• SRWILAKSARHZPR-UHFFFAOYSA-N 3-chlorobenzaldehyde Chemical compound ClC1=CC=CC(C=O)=C1 SRWILAKSARHZPR-UHFFFAOYSA-N 0.000 description 1
• XLEYXHRMSUPJST-UHFFFAOYSA-N 3-fluoro-4-phenylmethoxyaniline Chemical compound FC1=CC(N)=CC=C1OCC1=CC=CC=C1 XLEYXHRMSUPJST-UHFFFAOYSA-N 0.000 description 1
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
• VENLNRWSCKIJFP-UHFFFAOYSA-N 4-(5-methylsulfanyltetrazol-1-yl)phenol Chemical compound CSC1=NN=NN1C1=CC=C(O)C=C1 VENLNRWSCKIJFP-UHFFFAOYSA-N 0.000 description 1
• DSSMRGRPMUPZRP-UHFFFAOYSA-N 4-(5-propyltetrazol-1-yl)phenol Chemical compound CCCC1=NN=NN1C1=CC=C(O)C=C1 DSSMRGRPMUPZRP-UHFFFAOYSA-N 0.000 description 1
• BEOBZEOPTQQELP-UHFFFAOYSA-N 4-(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC=C(C=O)C=C1 BEOBZEOPTQQELP-UHFFFAOYSA-N 0.000 description 1
• YMQPKONILWWJQG-UHFFFAOYSA-N 4-bromo-1,2-difluorobenzene Chemical compound FC1=CC=C(Br)C=C1F YMQPKONILWWJQG-UHFFFAOYSA-N 0.000 description 1
• CVNOWLNNPYYEOH-UHFFFAOYSA-N 4-cyanophenol Chemical compound OC1=CC=C(C#N)C=C1 CVNOWLNNPYYEOH-UHFFFAOYSA-N 0.000 description 1
• LBUNNMJLXWQQBY-UHFFFAOYSA-N 4-fluorophenylboronic acid Chemical compound OB(O)C1=CC=C(F)C=C1 LBUNNMJLXWQQBY-UHFFFAOYSA-N 0.000 description 1
• FIIDVVUUWRJXLF-UHFFFAOYSA-N 4-phenylmethoxyaniline Chemical compound C1=CC(N)=CC=C1OCC1=CC=CC=C1 FIIDVVUUWRJXLF-UHFFFAOYSA-N 0.000 description 1
• YQFVRTPCYXZCII-UHFFFAOYSA-N 5-(5-cyclopropyltetrazol-1-yl)-2-methoxybenzaldehyde Chemical compound C1=C(C=O)C(OC)=CC=C1N1C(C2CC2)=NN=N1 YQFVRTPCYXZCII-UHFFFAOYSA-N 0.000 description 1
• PVRMGKBHWRHNIU-UHFFFAOYSA-N 5-(5-ethyltetrazol-1-yl)-2-hydroxybenzaldehyde Chemical compound CCC1=NN=NN1C1=CC=C(O)C(C=O)=C1 PVRMGKBHWRHNIU-UHFFFAOYSA-N 0.000 description 1
• SFDHVKDDZIMQON-UHFFFAOYSA-N 5-(bromomethyl)-2-methoxybenzaldehyde Chemical compound COC1=CC=C(CBr)C=C1C=O SFDHVKDDZIMQON-UHFFFAOYSA-N 0.000 description 1
• JQPZRQLUCZVWEO-UHFFFAOYSA-N 5-(chloromethyl)-2-methoxybenzaldehyde Chemical compound COC1=CC=C(CCl)C=C1C=O JQPZRQLUCZVWEO-UHFFFAOYSA-N 0.000 description 1
• FOEPLOQMUWYHBM-UHFFFAOYSA-N 5-(trifluoromethyl)-2h-tetrazole Chemical compound FC(F)(F)C=1N=NNN=1 FOEPLOQMUWYHBM-UHFFFAOYSA-N 0.000 description 1
• SQTWGTRJXOVEMT-UHFFFAOYSA-N 5-bromo-1-ethyltetrazole Chemical compound CCN1N=NN=C1Br SQTWGTRJXOVEMT-UHFFFAOYSA-N 0.000 description 1
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
• 235000019489 Almond oil Nutrition 0.000 description 1
• 208000024827 Alzheimer disease Diseases 0.000 description 1
• 206010002556 Ankylosing Spondylitis Diseases 0.000 description 1
• 208000019901 Anxiety disease Diseases 0.000 description 1
• 206010003571 Astrocytoma Diseases 0.000 description 1
• 208000025978 Athletic injury Diseases 0.000 description 1
• 108010006654 Bleomycin Proteins 0.000 description 1
• ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
• MGCWDDZRRSFHNG-UHFFFAOYSA-N BrC=1N=NN(N=1)CC1CC1 Chemical compound BrC=1N=NN(N=1)CC1CC1 MGCWDDZRRSFHNG-UHFFFAOYSA-N 0.000 description 1
• 206010006458 Bronchitis chronic Diseases 0.000 description 1
• HQOOYCJLKQRIDY-PWSUYJOCSA-N C1CC(=O)N[C@H]([C@@H]1[N+](=O)[O-])C2=CC=CC(=C2)CBr Chemical compound C1CC(=O)N[C@H]([C@@H]1[N+](=O)[O-])C2=CC=CC(=C2)CBr HQOOYCJLKQRIDY-PWSUYJOCSA-N 0.000 description 1
• NQHDWBLYQCGDOK-UHFFFAOYSA-N COC1=C(C=C(C=C1)N2C(=NN=N2)CCC(F)(F)F)C=O Chemical compound COC1=C(C=C(C=C1)N2C(=NN=N2)CCC(F)(F)F)C=O NQHDWBLYQCGDOK-UHFFFAOYSA-N 0.000 description 1
• MOGZQROIMKMDNS-UHFFFAOYSA-N CSC1=NN(N=N1)C2=CC=C(C=C2)O Chemical compound CSC1=NN(N=N1)C2=CC=C(C=C2)O MOGZQROIMKMDNS-UHFFFAOYSA-N 0.000 description 1
• 244000284152 Carapichea ipecacuanha Species 0.000 description 1
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
• DLGOEMSEDOSKAD-UHFFFAOYSA-N Carmustine Chemical compound ClCCNC(=O)N(N=O)CCCl DLGOEMSEDOSKAD-UHFFFAOYSA-N 0.000 description 1
• 206010064012 Central pain syndrome Diseases 0.000 description 1
• 208000000094 Chronic Pain Diseases 0.000 description 1
• CRUAYKJMEQVSIZ-OINVMNEBSA-N Cl.Cl.FC1=CC=C(C=C1)[C@@H]1NCCC[C@@H]1NCC1=C(C=CC(=C1)N1N=NN=C1)OC Chemical compound Cl.Cl.FC1=CC=C(C=C1)[C@@H]1NCCC[C@@H]1NCC1=C(C=CC(=C1)N1N=NN=C1)OC CRUAYKJMEQVSIZ-OINVMNEBSA-N 0.000 description 1
• 206010009900 Colitis ulcerative Diseases 0.000 description 1
• 229920002261 Corn starch Polymers 0.000 description 1
• 206010011224 Cough Diseases 0.000 description 1
• 241000699802 Cricetulus griseus Species 0.000 description 1
• 208000011231 Crohn disease Diseases 0.000 description 1
• XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
• CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 1
• 206010063057 Cystitis noninfective Diseases 0.000 description 1
• UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 description 1
• FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
• 108010092160 Dactinomycin Proteins 0.000 description 1
• 201000004624 Dermatitis Diseases 0.000 description 1
• 241000792859 Enema Species 0.000 description 1
• 244000166102 Eucalyptus leucoxylon Species 0.000 description 1
• 235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 1
• 206010015943 Eye inflammation Diseases 0.000 description 1
• 208000001640 Fibromyalgia Diseases 0.000 description 1
• GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 1
• 208000018522 Gastrointestinal disease Diseases 0.000 description 1
• 206010017964 Gastrointestinal infection Diseases 0.000 description 1
• 206010061974 Gastrointestinal obstruction Diseases 0.000 description 1
• 239000001828 Gelatine Substances 0.000 description 1
• 229920000084 Gum arabic Polymers 0.000 description 1
• 208000004898 Herpes Labialis Diseases 0.000 description 1
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
• VSNHCAURESNICA-UHFFFAOYSA-N Hydroxyurea Chemical compound NC(=O)NO VSNHCAURESNICA-UHFFFAOYSA-N 0.000 description 1
• 208000022559 Inflammatory bowel disease Diseases 0.000 description 1
• 208000027601 Inner ear disease Diseases 0.000 description 1
• FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 description 1
• GQYIWUVLTXOXAJ-UHFFFAOYSA-N Lomustine Chemical compound ClCCN(N=O)C(=O)NC1CCCCC1 GQYIWUVLTXOXAJ-UHFFFAOYSA-N 0.000 description 1
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
• 206010026749 Mania Diseases 0.000 description 1
• 229930195725 Mannitol Natural products 0.000 description 1
• 208000027530 Meniere disease Diseases 0.000 description 1
• 201000009906 Meningitis Diseases 0.000 description 1
• FQISKWAFAHGMGT-SGJOWKDISA-M Methylprednisolone sodium succinate Chemical compound [Na+].C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)[C@@](O)(C(=O)COC(=O)CCC([O-])=O)CC[C@H]21 FQISKWAFAHGMGT-SGJOWKDISA-M 0.000 description 1
• 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
• 208000007101 Muscle Cramp Diseases 0.000 description 1
• 241000282339 Mustela Species 0.000 description 1
• 241000282341 Mustela putorius furo Species 0.000 description 1
• 102000002002 Neurokinin-1 Receptors Human genes 0.000 description 1
• 108010040718 Neurokinin-1 Receptors Proteins 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
• 206010067152 Oral herpes Diseases 0.000 description 1
• 235000019502 Orange oil Nutrition 0.000 description 1
• 229910019142 PO4 Inorganic materials 0.000 description 1
• 208000004983 Phantom Limb Diseases 0.000 description 1
• 206010056238 Phantom pain Diseases 0.000 description 1
• 239000004698 Polyethylene Substances 0.000 description 1
• 208000028017 Psychotic disease Diseases 0.000 description 1
• 206010037464 Pulpitis dental Diseases 0.000 description 1
• 239000007868 Raney catalyst Substances 0.000 description 1
• NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
• 229910000564 Raney nickel Inorganic materials 0.000 description 1
• 206010039085 Rhinitis allergic Diseases 0.000 description 1
• 206010049002 Scar pain Diseases 0.000 description 1
• 206010039710 Scleroderma Diseases 0.000 description 1
• XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
• VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
• DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
• 239000004141 Sodium laurylsulphate Substances 0.000 description 1
• 239000004133 Sodium thiosulphate Substances 0.000 description 1
• 208000032851 Subarachnoid Hemorrhage Diseases 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
• 229930006000 Sucrose Natural products 0.000 description 1
• CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
• 206010042496 Sunburn Diseases 0.000 description 1
• 239000000150 Sympathomimetic Substances 0.000 description 1
• 208000026062 Tissue disease Diseases 0.000 description 1
• 201000006704 Ulcerative Colitis Diseases 0.000 description 1
• 206010046543 Urinary incontinence Diseases 0.000 description 1
• 208000024780 Urticaria Diseases 0.000 description 1
• 206010047163 Vasospasm Diseases 0.000 description 1
• JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 description 1
• WWWYPKGXYCLMJT-UHFFFAOYSA-N [4-[(2,2,2-trifluoroacetyl)amino]phenyl] benzoate Chemical compound C(C1=CC=CC=C1)(=O)OC1=CC=C(C=C1)NC(C(F)(F)F)=O WWWYPKGXYCLMJT-UHFFFAOYSA-N 0.000 description 1
• 230000003187 abdominal effect Effects 0.000 description 1
• 239000000205 acacia gum Substances 0.000 description 1
• 235000010489 acacia gum Nutrition 0.000 description 1
• 150000001241 acetals Chemical class 0.000 description 1
• DSFVQIUBODXRLL-UHFFFAOYSA-N acetamide;dihydrochloride Chemical compound Cl.Cl.CC(N)=O DSFVQIUBODXRLL-UHFFFAOYSA-N 0.000 description 1
• 239000008351 acetate buffer Substances 0.000 description 1
• 150000001242 acetic acid derivatives Chemical class 0.000 description 1
• 150000008065 acid anhydrides Chemical class 0.000 description 1
• 238000005903 acid hydrolysis reaction Methods 0.000 description 1
• 150000007513 acids Chemical class 0.000 description 1
• RJURFGZVJUQBHK-IIXSONLDSA-N actinomycin D Chemical compound C[C@H]1OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C(=O)[C@@H]2CCCN2C(=O)[C@@H](C(C)C)NC(=O)[C@H]1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)N[C@@H]4C(=O)N[C@@H](C(N5CCC[C@H]5C(=O)N(C)CC(=O)N(C)[C@@H](C(C)C)C(=O)O[C@@H]4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-IIXSONLDSA-N 0.000 description 1
• 230000010933 acylation Effects 0.000 description 1
• 238000005917 acylation reaction Methods 0.000 description 1
• 239000000853 adhesive Substances 0.000 description 1
• 239000012790 adhesive layer Substances 0.000 description 1
• 230000002411 adverse Effects 0.000 description 1
• 239000000443 aerosol Substances 0.000 description 1
• 125000003158 alcohol group Chemical group 0.000 description 1
• 125000003172 aldehyde group Chemical group 0.000 description 1
• 229930013930 alkaloid Natural products 0.000 description 1
• 230000029936 alkylation Effects 0.000 description 1
• 238000005804 alkylation reaction Methods 0.000 description 1
• 208000026935 allergic disease Diseases 0.000 description 1
• 208000028004 allergic respiratory disease Diseases 0.000 description 1
• 201000010105 allergic rhinitis Diseases 0.000 description 1
• 239000008168 almond oil Substances 0.000 description 1
• 208000008445 altitude sickness Diseases 0.000 description 1
• 125000003277 amino group Chemical group 0.000 description 1
• 239000003708 ampul Substances 0.000 description 1
• 238000004458 analytical method Methods 0.000 description 1
• 150000008064 anhydrides Chemical class 0.000 description 1
• 239000000730 antalgic agent Substances 0.000 description 1
• 230000001773 anti-convulsant effect Effects 0.000 description 1
• 230000003474 anti-emetic effect Effects 0.000 description 1
• 239000002260 anti-inflammatory agent Substances 0.000 description 1
• 229940121363 anti-inflammatory agent Drugs 0.000 description 1
• 230000003110 anti-inflammatory effect Effects 0.000 description 1
• 230000000340 anti-metabolite Effects 0.000 description 1
• 229940100197 antimetabolite Drugs 0.000 description 1
• 239000002256 antimetabolite Substances 0.000 description 1
• 239000003972 antineoplastic antibiotic Substances 0.000 description 1
• 230000036506 anxiety Effects 0.000 description 1
• 239000008135 aqueous vehicle Substances 0.000 description 1
• 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
• 125000005228 aryl sulfonate group Chemical group 0.000 description 1
• 208000006673 asthma Diseases 0.000 description 1
• 239000012298 atmosphere Substances 0.000 description 1
• 208000010668 atopic eczema Diseases 0.000 description 1
• 150000001540 azides Chemical class 0.000 description 1
• 230000001580 bacterial effect Effects 0.000 description 1
• 239000003637 basic solution Substances 0.000 description 1
• 239000011230 binding agent Substances 0.000 description 1
• 229960001561 bleomycin Drugs 0.000 description 1
• OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C OYVAGSVQBOHSSS-UAPAGMARSA-O 0.000 description 1
• 230000017531 blood circulation Effects 0.000 description 1
• 229910052796 boron Inorganic materials 0.000 description 1
• MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 1
• 210000004556 brain Anatomy 0.000 description 1
• AEILLAXRDHDKDY-UHFFFAOYSA-N bromomethylcyclopropane Chemical compound BrCC1CC1 AEILLAXRDHDKDY-UHFFFAOYSA-N 0.000 description 1
• 206010006451 bronchitis Diseases 0.000 description 1
• 239000000872 buffer Substances 0.000 description 1
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 1
• 150000001722 carbon compounds Chemical class 0.000 description 1
• 235000011089 carbon dioxide Nutrition 0.000 description 1
• 229960005243 carmustine Drugs 0.000 description 1
• 230000003197 catalytic effect Effects 0.000 description 1
• 239000001913 cellulose Substances 0.000 description 1
• 235000010980 cellulose Nutrition 0.000 description 1
• 229920002678 cellulose Polymers 0.000 description 1
• 208000015114 central nervous system disease Diseases 0.000 description 1
• 239000007795 chemical reaction product Substances 0.000 description 1
• 239000003153 chemical reaction reagent Substances 0.000 description 1
• 238000004296 chiral HPLC Methods 0.000 description 1
• 229960004630 chlorambucil Drugs 0.000 description 1
• JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 description 1
• 150000001805 chlorine compounds Chemical class 0.000 description 1
• 125000001309 chloro group Chemical group Cl* 0.000 description 1
• 208000007451 chronic bronchitis Diseases 0.000 description 1
• 150000001860 citric acid derivatives Chemical class 0.000 description 1
• 229940110456 cocoa butter Drugs 0.000 description 1
• 235000019868 cocoa butter Nutrition 0.000 description 1
• 229940075614 colloidal silicon dioxide Drugs 0.000 description 1
• 210000001072 colon Anatomy 0.000 description 1
• 239000008120 corn starch Substances 0.000 description 1
• 239000003246 corticosteroid Substances 0.000 description 1
• 229960001334 corticosteroids Drugs 0.000 description 1
• ROSHZDSDUDVRGH-UHFFFAOYSA-N cyanamide;dihydrochloride Chemical compound Cl.Cl.NC#N ROSHZDSDUDVRGH-UHFFFAOYSA-N 0.000 description 1
• 229960004397 cyclophosphamide Drugs 0.000 description 1
• 229960000684 cytarabine Drugs 0.000 description 1
• 229960003901 dacarbazine Drugs 0.000 description 1
• 229960000640 dactinomycin Drugs 0.000 description 1
• 230000003247 decreasing effect Effects 0.000 description 1
• 239000012024 dehydrating agents‎ Substances 0.000 description 1
• 239000003405 delayed action preparation Substances 0.000 description 1
• 235000019700 dicalcium phosphate Nutrition 0.000 description 1
• 230000001079 digestive effect Effects 0.000 description 1
• 238000007865 diluting Methods 0.000 description 1
• 229910001873 dinitrogen Inorganic materials 0.000 description 1
• 239000007884 disintegrant Substances 0.000 description 1
• 239000006185 dispersion Substances 0.000 description 1
• 208000002173 dizziness Diseases 0.000 description 1
• 229960004679 doxorubicin Drugs 0.000 description 1
• 201000006549 dyspepsia Diseases 0.000 description 1
• 229940047652 ear drops Drugs 0.000 description 1
• 239000008157 edible vegetable oil Substances 0.000 description 1
• 239000003480 eluent Substances 0.000 description 1
• 239000007920 enema Substances 0.000 description 1
• 229940079360 enema for constipation Drugs 0.000 description 1
• 230000002327 eosinophilic effect Effects 0.000 description 1
• 229960002179 ephedrine Drugs 0.000 description 1
• BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
• 239000002038 ethyl acetate fraction Substances 0.000 description 1
• VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 description 1
• 229960005420 etoposide Drugs 0.000 description 1
• 229940012356 eye drops Drugs 0.000 description 1
• 208000006275 fascioliasis Diseases 0.000 description 1
• 239000000945 filler Substances 0.000 description 1
• 229960002949 fluorouracil Drugs 0.000 description 1
• 239000006260 foam Substances 0.000 description 1
• 230000037406 food intake Effects 0.000 description 1
• 235000003599 food sweetener Nutrition 0.000 description 1
• 210000004211 gastric acid Anatomy 0.000 description 1
• 210000001156 gastric mucosa Anatomy 0.000 description 1
• 208000021302 gastroesophageal reflux disease Diseases 0.000 description 1
• 210000001035 gastrointestinal tract Anatomy 0.000 description 1
• 229920000159 gelatin Polymers 0.000 description 1
• 235000019322 gelatine Nutrition 0.000 description 1
• 239000011521 glass Substances 0.000 description 1
• 125000005456 glyceride group Chemical group 0.000 description 1
• 238000005469 granulation Methods 0.000 description 1
• 230000003179 granulation Effects 0.000 description 1
• 208000024798 heartburn Diseases 0.000 description 1
• QKGYJVXSKCDGOK-UHFFFAOYSA-N hexane;propan-2-ol Chemical compound CC(C)O.CCCCCC QKGYJVXSKCDGOK-UHFFFAOYSA-N 0.000 description 1
• 239000008240 homogeneous mixture Substances 0.000 description 1
• 150000004677 hydrates Chemical class 0.000 description 1
• 150000004678 hydrides Chemical class 0.000 description 1
• 150000003840 hydrochlorides Chemical class 0.000 description 1
• 230000002209 hydrophobic effect Effects 0.000 description 1
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
• 229960001330 hydroxycarbamide Drugs 0.000 description 1
• 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
• 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
• 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
• UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
• 230000036039 immunity Effects 0.000 description 1
• 239000007943 implant Substances 0.000 description 1
• 230000001939 inductive effect Effects 0.000 description 1
• 208000015181 infectious disease Diseases 0.000 description 1
• 208000027866 inflammatory disease Diseases 0.000 description 1
• 206010022000 influenza Diseases 0.000 description 1
• 238000001802 infusion Methods 0.000 description 1
• 230000002401 inhibitory effect Effects 0.000 description 1
• 230000005764 inhibitory process Effects 0.000 description 1
• 208000014674 injury Diseases 0.000 description 1
• 210000001937 intercostal nerve Anatomy 0.000 description 1
• UEXQBEVWFZKHNB-UHFFFAOYSA-N intermediate 29 Natural products C1=CC(N)=CC=C1NC1=NC=CC=N1 UEXQBEVWFZKHNB-UHFFFAOYSA-N 0.000 description 1
• 238000010255 intramuscular injection Methods 0.000 description 1
• 239000007927 intramuscular injection 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
• 229960005208 ipecacuanha Drugs 0.000 description 1
• FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 1
• 230000007803 itching Effects 0.000 description 1
• 239000000787 lecithin Substances 0.000 description 1
• 235000010445 lecithin Nutrition 0.000 description 1
• 229940067606 lecithin Drugs 0.000 description 1
• 230000003902 lesion Effects 0.000 description 1
• 239000012669 liquid formulation Substances 0.000 description 1
• 239000012280 lithium aluminium hydride Substances 0.000 description 1
• 230000033001 locomotion Effects 0.000 description 1
• 229960002247 lomustine Drugs 0.000 description 1
• 230000007774 longterm Effects 0.000 description 1
• 239000006210 lotion Substances 0.000 description 1
• 239000007937 lozenge Substances 0.000 description 1
• 239000011777 magnesium Substances 0.000 description 1
• 229910052749 magnesium Inorganic materials 0.000 description 1
• 230000014759 maintenance of location Effects 0.000 description 1
• 150000002688 maleic acid derivatives Chemical class 0.000 description 1
• 239000000594 mannitol Substances 0.000 description 1
• 235000010355 mannitol Nutrition 0.000 description 1
• 238000004949 mass spectrometry Methods 0.000 description 1
• 210000004086 maxillary sinus Anatomy 0.000 description 1
• 235000012054 meals Nutrition 0.000 description 1
• 238000002844 melting Methods 0.000 description 1
• 230000008018 melting Effects 0.000 description 1
• 230000005906 menstruation Effects 0.000 description 1
• 208000030159 metabolic disease Diseases 0.000 description 1
• AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
• 229960000485 methotrexate Drugs 0.000 description 1
• PSCXCIPPRCFAAO-UHFFFAOYSA-N methyl 5-amino-2-methoxybenzoate Chemical compound COC(=O)C1=CC(N)=CC=C1OC PSCXCIPPRCFAAO-UHFFFAOYSA-N 0.000 description 1
• 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
• 229960002216 methylparaben Drugs 0.000 description 1
• 229960004584 methylprednisolone Drugs 0.000 description 1
• 229940016286 microcrystalline cellulose Drugs 0.000 description 1
• 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
• 239000008108 microcrystalline cellulose Substances 0.000 description 1
• 150000007522 mineralic acids Chemical class 0.000 description 1
• 229960004857 mitomycin Drugs 0.000 description 1
• 238000002156 mixing Methods 0.000 description 1
• 239000002808 molecular sieve Substances 0.000 description 1
• 229960005181 morphine Drugs 0.000 description 1
• 201000003152 motion sickness Diseases 0.000 description 1
• 201000006417 multiple sclerosis Diseases 0.000 description 1
• 210000003205 muscle Anatomy 0.000 description 1
• 208000010125 myocardial infarction Diseases 0.000 description 1
• 239000003158 myorelaxant agent Substances 0.000 description 1
• 230000001670 myorelaxant effect Effects 0.000 description 1
• PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-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
• 229940100662 nasal drops Drugs 0.000 description 1
• 210000005036 nerve Anatomy 0.000 description 1
• 208000021722 neuropathic pain Diseases 0.000 description 1
• 201000001119 neuropathy Diseases 0.000 description 1
• 230000007823 neuropathy Effects 0.000 description 1
• 229910017604 nitric acid Inorganic materials 0.000 description 1
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
• 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
• 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
• 239000002687 nonaqueous vehicle Substances 0.000 description 1
• 239000000014 opioid analgesic Substances 0.000 description 1
• 229940005483 opioid analgesics Drugs 0.000 description 1
• 239000010502 orange oil Substances 0.000 description 1
• 150000007524 organic acids Chemical class 0.000 description 1
• 125000002524 organometallic group Chemical group 0.000 description 1
• 201000008482 osteoarthritis Diseases 0.000 description 1
• 210000001672 ovary Anatomy 0.000 description 1
• 235000006408 oxalic acid Nutrition 0.000 description 1
• 239000007800 oxidant agent Substances 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
• RUNIEFCRNHEYJO-UHFFFAOYSA-N oxolane;sodium Chemical compound [Na].C1CCOC1 RUNIEFCRNHEYJO-UHFFFAOYSA-N 0.000 description 1
• 229910052760 oxygen Inorganic materials 0.000 description 1
• 229960001528 oxymetazoline Drugs 0.000 description 1
• 229910003445 palladium oxide Inorganic materials 0.000 description 1
• JQPTYAILLJKUCY-UHFFFAOYSA-N palladium(ii) oxide Chemical compound [O-2].[Pd+2] JQPTYAILLJKUCY-UHFFFAOYSA-N 0.000 description 1
• 206010034674 peritonitis Diseases 0.000 description 1
• 150000002978 peroxides Chemical class 0.000 description 1
• 235000021317 phosphate Nutrition 0.000 description 1
• 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
• 239000002574 poison Substances 0.000 description 1
• 231100000614 poison Toxicity 0.000 description 1
• 229920000058 polyacrylate Polymers 0.000 description 1
• 229920000573 polyethylene Polymers 0.000 description 1
• 229920000098 polyolefin Polymers 0.000 description 1
• 229920001296 polysiloxane Polymers 0.000 description 1
• 229920002689 polyvinyl acetate Polymers 0.000 description 1
• 239000011118 polyvinyl acetate Substances 0.000 description 1
• 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
• 230000002980 postoperative effect Effects 0.000 description 1
• 229920001592 potato starch Polymers 0.000 description 1
• 230000003389 potentiating effect Effects 0.000 description 1
• 238000002953 preparative HPLC Methods 0.000 description 1
• 230000002335 preservative effect Effects 0.000 description 1
• CPTBDICYNRMXFX-UHFFFAOYSA-N procarbazine Chemical compound CNNCC1=CC=C(C(=O)NC(C)C)C=C1 CPTBDICYNRMXFX-UHFFFAOYSA-N 0.000 description 1
• 229960000624 procarbazine Drugs 0.000 description 1
• SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
• AURNFBUHBDLHKR-UHFFFAOYSA-N propan-2-one;dihydrochloride Chemical compound Cl.Cl.CC(C)=O AURNFBUHBDLHKR-UHFFFAOYSA-N 0.000 description 1
• 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
• QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical class CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
• 125000006239 protecting group Chemical group 0.000 description 1
• KWGRBVOPPLSCSI-WCBMZHEXSA-N pseudoephedrine Chemical compound CN[C@@H](C)[C@@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WCBMZHEXSA-N 0.000 description 1
• 229960003908 pseudoephedrine Drugs 0.000 description 1
• 238000010926 purge Methods 0.000 description 1
• 230000011514 reflex Effects 0.000 description 1
• 206010039073 rheumatoid arthritis Diseases 0.000 description 1
• 229920006395 saturated elastomer Polymers 0.000 description 1
• 201000000980 schizophrenia Diseases 0.000 description 1
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 229910052710 silicon Inorganic materials 0.000 description 1
• 239000010703 silicon Substances 0.000 description 1
• 229920005573 silicon-containing polymer Polymers 0.000 description 1
• 210000002027 skeletal muscle Anatomy 0.000 description 1
• 208000017520 skin disease Diseases 0.000 description 1
• 239000001632 sodium acetate Substances 0.000 description 1
• 235000017281 sodium acetate Nutrition 0.000 description 1
• URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
• 235000017557 sodium bicarbonate Nutrition 0.000 description 1
• WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
• 239000011780 sodium chloride Substances 0.000 description 1
• BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
• HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
• 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
• 229940001584 sodium metabisulfite Drugs 0.000 description 1
• 235000010262 sodium metabisulphite Nutrition 0.000 description 1
• 229940079832 sodium starch glycolate Drugs 0.000 description 1
• 239000008109 sodium starch glycolate Substances 0.000 description 1
• 229920003109 sodium starch glycolate Polymers 0.000 description 1
• 235000010265 sodium sulphite Nutrition 0.000 description 1
• AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
• PODWXQQNRWNDGD-UHFFFAOYSA-L sodium thiosulfate pentahydrate Chemical compound O.O.O.O.O.[Na+].[Na+].[O-]S([S-])(=O)=O PODWXQQNRWNDGD-UHFFFAOYSA-L 0.000 description 1
• 235000019345 sodium thiosulphate Nutrition 0.000 description 1
• 235000010199 sorbic acid Nutrition 0.000 description 1
• 239000004334 sorbic acid Substances 0.000 description 1
• 229940075582 sorbic acid Drugs 0.000 description 1
• 239000000600 sorbitol Substances 0.000 description 1
• 235000010356 sorbitol Nutrition 0.000 description 1
• 230000000087 stabilizing effect Effects 0.000 description 1
• 230000001954 sterilising effect Effects 0.000 description 1
• 150000003890 succinate salts Chemical class 0.000 description 1
• 239000005720 sucrose Substances 0.000 description 1
• 238000009495 sugar coating Methods 0.000 description 1
• 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
• 239000002511 suppository base Substances 0.000 description 1
• 230000001629 suppression Effects 0.000 description 1
• 238000001356 surgical procedure Methods 0.000 description 1
• 239000003765 sweetening agent Substances 0.000 description 1
• 229940127230 sympathomimetic drug Drugs 0.000 description 1
• 238000003786 synthesis reaction Methods 0.000 description 1
• 230000009885 systemic effect Effects 0.000 description 1
• 201000000596 systemic lupus erythematosus Diseases 0.000 description 1
• 239000000454 talc Substances 0.000 description 1
• 229910052623 talc Inorganic materials 0.000 description 1
• 150000003892 tartrate salts Chemical class 0.000 description 1
• 230000002123 temporal effect Effects 0.000 description 1
• 230000001225 therapeutic effect Effects 0.000 description 1
• 238000002560 therapeutic procedure Methods 0.000 description 1
• 210000000115 thoracic cavity Anatomy 0.000 description 1
• 208000004371 toothache Diseases 0.000 description 1
• 231100000331 toxic Toxicity 0.000 description 1
• 230000002588 toxic effect Effects 0.000 description 1
• 239000003053 toxin Substances 0.000 description 1
• 231100000765 toxin Toxicity 0.000 description 1
• 108700012359 toxins Proteins 0.000 description 1
• 238000012549 training Methods 0.000 description 1
• 229940100640 transdermal system Drugs 0.000 description 1
• 230000008733 trauma Effects 0.000 description 1
• 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
• 206010044652 trigeminal neuralgia Diseases 0.000 description 1
• 238000000825 ultraviolet detection Methods 0.000 description 1
• 230000002792 vascular Effects 0.000 description 1
• 235000015112 vegetable and seed oil Nutrition 0.000 description 1
• 239000008158 vegetable oil Substances 0.000 description 1
• 208000027491 vestibular disease Diseases 0.000 description 1
• 229960003048 vinblastine Drugs 0.000 description 1
• JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
• OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
• 229960004528 vincristine Drugs 0.000 description 1
• OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
• 230000003612 virological effect Effects 0.000 description 1
• 210000001835 viscera Anatomy 0.000 description 1
• 239000000080 wetting agent Substances 0.000 description 1
• 239000008096 xylene Substances 0.000 description 1