TW201443054A - 化合物 - Google Patents

Info

Publication number

TW201443054A

TW201443054A TW103102388A TW103102388A TW201443054A TW 201443054 A TW201443054 A TW 201443054A TW 103102388 A TW103102388 A TW 103102388A TW 103102388 A TW103102388 A TW 103102388A TW 201443054 A TW201443054 A TW 201443054A

Authority

TW

Taiwan

Prior art keywords

oxy

prepared

dihydroimidazo

esi

compound

Prior art date

2013-01-25

Links

• Espacenet
• Global Dossier
• Discuss

• 150000001875 compounds Chemical class 0.000 title claims abstract description 396
• 238000000034 method Methods 0.000 claims abstract description 248
• 238000011282 treatment Methods 0.000 claims abstract description 30
• 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 27
• 201000001320 Atherosclerosis Diseases 0.000 claims abstract description 18
• 150000003839 salts Chemical class 0.000 claims description 103
• -1 R c is H Chemical group 0.000 claims description 69
• 229910052739 hydrogen Inorganic materials 0.000 claims description 64
• 229910052731 fluorine Inorganic materials 0.000 claims description 52
• 125000001424 substituent group Chemical group 0.000 claims description 29
• 125000005843 halogen group Chemical group 0.000 claims description 28
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 24
• 230000004770 neurodegeneration Effects 0.000 claims description 23
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 23
• 239000008194 pharmaceutical composition Substances 0.000 claims description 23
• 125000004076 pyridyl group Chemical group 0.000 claims description 19
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
• 239000002253 acid Substances 0.000 claims description 16
• 239000003814 drug Substances 0.000 claims description 15
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 15
• 125000000217 alkyl group Chemical group 0.000 claims description 11
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
• 229910052801 chlorine Inorganic materials 0.000 claims description 8
• 229910052799 carbon Inorganic materials 0.000 claims description 7
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
• 238000004519 manufacturing process Methods 0.000 claims description 7
• 238000002560 therapeutic procedure Methods 0.000 claims description 6
• 125000001544 thienyl group Chemical group 0.000 claims description 6
• 239000012458 free base Substances 0.000 claims description 5
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 64
• 201000010099 disease Diseases 0.000 abstract description 61
• 239000000203 mixture Substances 0.000 abstract description 43
• 230000000694 effects Effects 0.000 abstract description 28
• 230000008569 process Effects 0.000 abstract description 19
• 238000002360 preparation method Methods 0.000 abstract description 12
• 102000016752 1-Alkyl-2-acetylglycerophosphocholine Esterase Human genes 0.000 abstract description 3
• 108010024976 Asparaginase Proteins 0.000 abstract description 3
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 235
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 196
• 230000014759 maintenance of location Effects 0.000 description 188
• 239000007858 starting material Substances 0.000 description 142
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 96
• 235000019439 ethyl acetate Nutrition 0.000 description 89
• 239000011541 reaction mixture Substances 0.000 description 81
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 73
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 66
• 239000000243 solution Substances 0.000 description 61
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 55
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 39
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 39
• YHLZLQSMYFVIPE-UHFFFAOYSA-N 7-chloro-1,2,2-trimethyl-3h-imidazo[1,2-c]pyrimidin-5-one Chemical compound ClC1=NC(=O)N2CC(C)(C)N(C)C2=C1 YHLZLQSMYFVIPE-UHFFFAOYSA-N 0.000 description 38
• 238000000746 purification Methods 0.000 description 38
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 36
• 238000004458 analytical method Methods 0.000 description 31
• 239000011734 sodium Substances 0.000 description 30
• 238000003556 assay Methods 0.000 description 27
• 239000007787 solid Substances 0.000 description 25
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
• 239000003358 phospholipase A2 inhibitor Substances 0.000 description 22
• 239000000047 product Substances 0.000 description 22
• 238000006243 chemical reaction Methods 0.000 description 21
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 20
• 230000008499 blood brain barrier function Effects 0.000 description 20
• 210000001218 blood-brain barrier Anatomy 0.000 description 20
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
• FNRUZVGFMVXMFM-YFKPBYRVSA-N (2s)-7-chloro-1,2-dimethyl-2,3-dihydroimidazo[1,2-c]pyrimidin-5-one Chemical compound C([C@@H](N1C)C)N2C1=CC(Cl)=NC2=O FNRUZVGFMVXMFM-YFKPBYRVSA-N 0.000 description 16
• 201000004810 Vascular dementia Diseases 0.000 description 16
• 208000029725 Metabolic bone disease Diseases 0.000 description 15
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 15
• 238000010189 synthetic method Methods 0.000 description 15
• 239000012267 brine Substances 0.000 description 14
• 239000000460 chlorine Substances 0.000 description 14
• OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 14
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
• 239000002904 solvent Substances 0.000 description 14
• 208000024891 symptom Diseases 0.000 description 14
• JPHKMYXKNKLNDF-UHFFFAOYSA-N 3,4-difluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1F JPHKMYXKNKLNDF-UHFFFAOYSA-N 0.000 description 12
• 208000001344 Macular Edema Diseases 0.000 description 12
• 206010025415 Macular oedema Diseases 0.000 description 12
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
• 239000003795 chemical substances by application Substances 0.000 description 12
• 210000002540 macrophage Anatomy 0.000 description 12
• 201000010230 macular retinal edema Diseases 0.000 description 12
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
• 239000012453 solvate Substances 0.000 description 12
• 238000003756 stirring Methods 0.000 description 12
• FNRUZVGFMVXMFM-UHFFFAOYSA-N 7-chloro-1,2-dimethyl-2,3-dihydroimidazo[1,2-c]pyrimidin-5-one Chemical compound CN1C(C)CN2C1=CC(Cl)=NC2=O FNRUZVGFMVXMFM-UHFFFAOYSA-N 0.000 description 11
• 229910000104 sodium hydride Inorganic materials 0.000 description 11
• 239000012043 crude product Substances 0.000 description 10
• 206010012601 diabetes mellitus Diseases 0.000 description 10
• 230000006870 function Effects 0.000 description 10
• 239000011780 sodium chloride Substances 0.000 description 10
• DPVIABCMTHHTGB-UHFFFAOYSA-N 2,4,6-trichloropyrimidine Chemical compound ClC1=CC(Cl)=NC(Cl)=N1 DPVIABCMTHHTGB-UHFFFAOYSA-N 0.000 description 9
• JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 9
• UMCMPZBLKLEWAF-BCTGSCMUSA-N 3-[(3-cholamidopropyl)dimethylammonio]propane-1-sulfonate Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCCC[N+](C)(C)CCCS([O-])(=O)=O)C)[C@@]2(C)[C@@H](O)C1 UMCMPZBLKLEWAF-BCTGSCMUSA-N 0.000 description 9
• 239000007995 HEPES buffer Substances 0.000 description 9
• 102100026918 Phospholipase A2 Human genes 0.000 description 9
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
• 239000002552 dosage form Substances 0.000 description 9
• 239000007788 liquid Substances 0.000 description 9
• 201000006417 multiple sclerosis Diseases 0.000 description 9
• 239000012071 phase Substances 0.000 description 9
• 230000002829 reductive effect Effects 0.000 description 9
• IGECFZYBIJQXPU-UHFFFAOYSA-N tert-butyl 7-chloro-2,2-dimethyl-5-oxo-3h-imidazo[1,2-c]pyrimidine-1-carboxylate Chemical compound ClC1=NC(=O)N2CC(C)(C)N(C(=O)OC(C)(C)C)C2=C1 IGECFZYBIJQXPU-UHFFFAOYSA-N 0.000 description 9
• DZOMRYLZWBYFLF-UHFFFAOYSA-N (2-acetyloxy-3-octadecylsulfanylpropyl) 2-(trimethylazaniumyl)ethyl phosphate Chemical compound CCCCCCCCCCCCCCCCCCSCC(OC(C)=O)COP([O-])(=O)OCC[N+](C)(C)C DZOMRYLZWBYFLF-UHFFFAOYSA-N 0.000 description 8
• RYCNUMLMNKHWPZ-SNVBAGLBSA-N 1-acetyl-sn-glycero-3-phosphocholine Chemical compound CC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C RYCNUMLMNKHWPZ-SNVBAGLBSA-N 0.000 description 8
• 239000012131 assay buffer Substances 0.000 description 8
• 230000015572 biosynthetic process Effects 0.000 description 8
• 239000003153 chemical reaction reagent Substances 0.000 description 8
• 230000002401 inhibitory effect Effects 0.000 description 8
• 239000010410 layer Substances 0.000 description 8
• 208000002780 macular degeneration Diseases 0.000 description 8
• 230000010287 polarization Effects 0.000 description 8
• 230000002265 prevention Effects 0.000 description 8
• 238000011160 research Methods 0.000 description 8
• 239000011550 stock solution Substances 0.000 description 8
• 239000000725 suspension Substances 0.000 description 8
• GNQLTCVBSGVGHC-UHFFFAOYSA-N (3,4-difluorophenyl)methanol Chemical compound OCC1=CC=C(F)C(F)=C1 GNQLTCVBSGVGHC-UHFFFAOYSA-N 0.000 description 7
• JSFGDUIJQWWBGY-UHFFFAOYSA-N 2,3-difluorobenzyl alcohol Chemical compound OCC1=CC=CC(F)=C1F JSFGDUIJQWWBGY-UHFFFAOYSA-N 0.000 description 7
• 108700003842 2-acetyl-S-octadecyl-1-thioglycero-3-phosphocholine Proteins 0.000 description 7
• PCOFIIVWHXIDGT-UHFFFAOYSA-N 3-(hydroxymethyl)benzonitrile Chemical compound OCC1=CC=CC(C#N)=C1 PCOFIIVWHXIDGT-UHFFFAOYSA-N 0.000 description 7
• 102000004190 Enzymes Human genes 0.000 description 7
• 108090000790 Enzymes Proteins 0.000 description 7
• 208000030136 Marchiafava-Bignami Disease Diseases 0.000 description 7
• 101710096328 Phospholipase A2 Proteins 0.000 description 7
• DUXJDKCZMCVGOI-UHFFFAOYSA-N [3,5-difluoro-4-[2-(trifluoromethyl)pyridin-4-yl]oxyphenyl]methanol Chemical compound FC1=CC(CO)=CC(F)=C1OC1=CC=NC(C(F)(F)F)=C1 DUXJDKCZMCVGOI-UHFFFAOYSA-N 0.000 description 7
• OCFOZIJBYNUXOK-UHFFFAOYSA-N [3-fluoro-4-[2-(trifluoromethyl)pyridin-4-yl]oxyphenyl]methanol Chemical compound FC1=CC(CO)=CC=C1OC1=CC=NC(C(F)(F)F)=C1 OCFOZIJBYNUXOK-UHFFFAOYSA-N 0.000 description 7
• 239000002585 base Substances 0.000 description 7
• 201000002491 encephalomyelitis Diseases 0.000 description 7
• 238000002474 experimental method Methods 0.000 description 7
• 230000002757 inflammatory effect Effects 0.000 description 7
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
• 150000003904 phospholipids Chemical class 0.000 description 7
• 230000000750 progressive effect Effects 0.000 description 7
• PXWASTUQOKUFKY-BYPYZUCNSA-N (2s)-2-(methylamino)propan-1-ol Chemical compound CN[C@@H](C)CO PXWASTUQOKUFKY-BYPYZUCNSA-N 0.000 description 6
• LOGIHEKXJKHXEC-UHFFFAOYSA-N (3,5-difluorophenyl)methanol Chemical compound OCC1=CC(F)=CC(F)=C1 LOGIHEKXJKHXEC-UHFFFAOYSA-N 0.000 description 6
• YHPVIBUEXBEHPV-UHFFFAOYSA-N 2,6-dihydro-1h-pyrimidin-5-one Chemical compound O=C1CNCN=C1 YHPVIBUEXBEHPV-UHFFFAOYSA-N 0.000 description 6
• OOVBMNHJMJKTRH-UHFFFAOYSA-N 2-fluoro-5-(hydroxymethyl)benzonitrile Chemical compound OCC1=CC=C(F)C(C#N)=C1 OOVBMNHJMJKTRH-UHFFFAOYSA-N 0.000 description 6
• NLAVHUUABUFSIG-UHFFFAOYSA-N 3,4,5-trifluorobenzaldehyde Chemical compound FC1=CC(C=O)=CC(F)=C1F NLAVHUUABUFSIG-UHFFFAOYSA-N 0.000 description 6
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
• 208000002691 Choroiditis Diseases 0.000 description 6
• 206010061218 Inflammation Diseases 0.000 description 6
• GHAZCVNUKKZTLG-UHFFFAOYSA-N N-ethyl-succinimide Natural products CCN1C(=O)CCC1=O GHAZCVNUKKZTLG-UHFFFAOYSA-N 0.000 description 6
• HDFGOPSGAURCEO-UHFFFAOYSA-N N-ethylmaleimide Chemical compound CCN1C(=O)C=CC1=O HDFGOPSGAURCEO-UHFFFAOYSA-N 0.000 description 6
• 208000001132 Osteoporosis Diseases 0.000 description 6
• 208000003971 Posterior uveitis Diseases 0.000 description 6
• GGEQJEMZBDACIS-UHFFFAOYSA-N [3-fluoro-4-[6-(trifluoromethyl)pyridin-3-yl]oxyphenyl]methanol Chemical compound FC1=CC(CO)=CC=C1OC1=CC=C(C(F)(F)F)N=C1 GGEQJEMZBDACIS-UHFFFAOYSA-N 0.000 description 6
• 125000004429 atom Chemical group 0.000 description 6
• 239000013058 crude material Substances 0.000 description 6
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
• 230000004054 inflammatory process Effects 0.000 description 6
• 230000005764 inhibitory process Effects 0.000 description 6
• 239000011159 matrix material Substances 0.000 description 6
• BZLVMXJERCGZMT-UHFFFAOYSA-N methyl tert-butyl ether Substances COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 6
• 229910000027 potassium carbonate Inorganic materials 0.000 description 6
• 238000010791 quenching Methods 0.000 description 6
• 230000000171 quenching effect Effects 0.000 description 6
• 238000003786 synthesis reaction Methods 0.000 description 6
• 238000012360 testing method Methods 0.000 description 6
• 229940124597 therapeutic agent Drugs 0.000 description 6
• 210000001519 tissue Anatomy 0.000 description 6
• HRSFRSLKOPFWMZ-UHFFFAOYSA-N (3,4,5-trifluorophenyl)methanol Chemical compound OCC1=CC(F)=C(F)C(F)=C1 HRSFRSLKOPFWMZ-UHFFFAOYSA-N 0.000 description 5
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 5
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
• 206010012689 Diabetic retinopathy Diseases 0.000 description 5
• 208000010412 Glaucoma Diseases 0.000 description 5
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
• 229910010082 LiAlH Inorganic materials 0.000 description 5
• 208000018737 Parkinson disease Diseases 0.000 description 5
• 241000700159 Rattus Species 0.000 description 5
• 229920002472 Starch Polymers 0.000 description 5
• UXRDAJMOOGEIAQ-CKOZHMEPSA-N [(8r,9s,10r,13s,14s,17r)-17-acetyl-10,13-dimethyl-16-methylidene-3-oxo-1,2,8,9,11,12,14,15-octahydrocyclopenta[a]phenanthren-17-yl] acetate Chemical compound C1=CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC(=C)[C@](OC(=O)C)(C(C)=O)[C@@]1(C)CC2 UXRDAJMOOGEIAQ-CKOZHMEPSA-N 0.000 description 5
• 206010064930 age-related macular degeneration Diseases 0.000 description 5
• 210000004556 brain Anatomy 0.000 description 5
• 125000004432 carbon atom Chemical group C* 0.000 description 5
• 229940079593 drug Drugs 0.000 description 5
• 235000021588 free fatty acids Nutrition 0.000 description 5
• 239000003112 inhibitor Substances 0.000 description 5
• 150000002632 lipids Chemical class 0.000 description 5
• 230000001537 neural effect Effects 0.000 description 5
• 239000012044 organic layer Substances 0.000 description 5
• 239000003208 petroleum Substances 0.000 description 5
• 125000006239 protecting group Chemical group 0.000 description 5
• 238000010992 reflux Methods 0.000 description 5
• 238000013207 serial dilution Methods 0.000 description 5
• 229940032147 starch Drugs 0.000 description 5
• 239000008107 starch Substances 0.000 description 5
• PYYIRLBSHVDFMO-BYPYZUCNSA-N (2S)-7-chloro-2-methyl-2,3-dihydro-1H-imidazo[1,2-c]pyrimidin-5-one Chemical compound C([C@@H](N1)C)N2C1=CC(Cl)=NC2=O PYYIRLBSHVDFMO-BYPYZUCNSA-N 0.000 description 4
• YPPZOKNKENLFTE-AREMUKBSSA-N 1-o-hexadecyl-2-deoxy-2-thio-s-acetyl-sn-glyceryl-3-phosphorylcholine Chemical compound CCCCCCCCCCCCCCCCOC[C@@H](SC(C)=O)COP([O-])(=O)OCC[N+](C)(C)C YPPZOKNKENLFTE-AREMUKBSSA-N 0.000 description 4
• NIJZBWHOHNWJBX-UHFFFAOYSA-N 2,4-difluorobenzyl alcohol 2,4-difluoro-1-(hydroxymethyl)benzene Chemical compound OCC1=CC=C(F)C=C1F NIJZBWHOHNWJBX-UHFFFAOYSA-N 0.000 description 4
• LKHCWMQMRXAPHX-UHFFFAOYSA-N 2-(trifluoromethyl)-1h-pyridin-4-one Chemical compound OC1=CC=NC(C(F)(F)F)=C1 LKHCWMQMRXAPHX-UHFFFAOYSA-N 0.000 description 4
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
• YUUZFMWMDPHTQS-UHFFFAOYSA-N 5-(trifluoromethyl)pyridin-3-ol Chemical compound OC1=CN=CC(C(F)(F)F)=C1 YUUZFMWMDPHTQS-UHFFFAOYSA-N 0.000 description 4
• OEJUZOMKTWUSBP-UHFFFAOYSA-N 7-chloro-2,2-dimethyl-1,3-dihydroimidazo[1,2-c]pyrimidin-5-one Chemical compound N1C(C)(C)CN2C1=CC(Cl)=NC2=O OEJUZOMKTWUSBP-UHFFFAOYSA-N 0.000 description 4
• OACRSGWNXCQXRG-UHFFFAOYSA-N 7-chloro-2,2-dimethyl-1-methylsulfonyl-3h-imidazo[1,2-c]pyrimidin-5-one Chemical compound CS(=O)(=O)N1C(C)(C)CN2C1=CC(Cl)=NC2=O OACRSGWNXCQXRG-UHFFFAOYSA-N 0.000 description 4
• 102000004127 Cytokines Human genes 0.000 description 4
• 108090000695 Cytokines Proteins 0.000 description 4
• 206010012688 Diabetic retinal oedema Diseases 0.000 description 4
• 206010048554 Endothelial dysfunction Diseases 0.000 description 4
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
• 108090001030 Lipoproteins Proteins 0.000 description 4
• 102000004895 Lipoproteins Human genes 0.000 description 4
• 210000004322 M2 macrophage Anatomy 0.000 description 4
• 206010049088 Osteopenia Diseases 0.000 description 4
• URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 4
• 208000006011 Stroke Diseases 0.000 description 4
• XHHMYFGHIMQOQW-UHFFFAOYSA-N [3,5-difluoro-4-[5-(trifluoromethyl)pyridin-3-yl]oxyphenyl]methanol Chemical compound FC1=CC(CO)=CC(F)=C1OC1=CN=CC(C(F)(F)F)=C1 XHHMYFGHIMQOQW-UHFFFAOYSA-N 0.000 description 4
• KFRJQOXIOLVYKL-UHFFFAOYSA-N [3-fluoro-4-[2-(trifluoromethyl)pyrimidin-5-yl]oxyphenyl]methanol Chemical compound FC1=CC(CO)=CC=C1OC1=CN=C(C(F)(F)F)N=C1 KFRJQOXIOLVYKL-UHFFFAOYSA-N 0.000 description 4
• TZIBZKKXSMTNGE-UHFFFAOYSA-N [3-fluoro-4-[5-(trifluoromethyl)pyridin-3-yl]oxyphenyl]methanol Chemical compound FC1=CC(CO)=CC=C1OC1=CN=CC(C(F)(F)F)=C1 TZIBZKKXSMTNGE-UHFFFAOYSA-N 0.000 description 4
• 230000002378 acidificating effect Effects 0.000 description 4
• 206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 4
• 239000011230 binding agent Substances 0.000 description 4
• 210000000988 bone and bone Anatomy 0.000 description 4
• 210000003690 classically activated macrophage Anatomy 0.000 description 4
• 238000003776 cleavage reaction Methods 0.000 description 4
• 238000002648 combination therapy Methods 0.000 description 4
• 230000003247 decreasing effect Effects 0.000 description 4
• 201000011190 diabetic macular edema Diseases 0.000 description 4
• ADEBPBSSDYVVLD-UHFFFAOYSA-N donepezil Chemical compound O=C1C=2C=C(OC)C(OC)=CC=2CC1CC(CC1)CCN1CC1=CC=CC=C1 ADEBPBSSDYVVLD-UHFFFAOYSA-N 0.000 description 4
• 230000008694 endothelial dysfunction Effects 0.000 description 4
• 208000030533 eye disease Diseases 0.000 description 4
• 238000009472 formulation Methods 0.000 description 4
• 150000004677 hydrates Chemical class 0.000 description 4
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
• 229910052500 inorganic mineral Inorganic materials 0.000 description 4
• 208000028867 ischemia Diseases 0.000 description 4
• ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
• 210000004698 lymphocyte Anatomy 0.000 description 4
• 235000010755 mineral Nutrition 0.000 description 4
• 239000011707 mineral Substances 0.000 description 4
• 210000001616 monocyte Anatomy 0.000 description 4
• 208000010125 myocardial infarction Diseases 0.000 description 4
• 239000003921 oil Substances 0.000 description 4
• 230000003647 oxidation Effects 0.000 description 4
• 238000007254 oxidation reaction Methods 0.000 description 4
• 108010071584 oxidized low density lipoprotein Proteins 0.000 description 4
• HYAFETHFCAUJAY-UHFFFAOYSA-N pioglitazone Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 HYAFETHFCAUJAY-UHFFFAOYSA-N 0.000 description 4
• 239000000843 powder Substances 0.000 description 4
• 238000011533 pre-incubation Methods 0.000 description 4
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
• 206010039073 rheumatoid arthritis Diseases 0.000 description 4
• 230000007017 scission Effects 0.000 description 4
• 235000019698 starch Nutrition 0.000 description 4
• 239000000126 substance Substances 0.000 description 4
• 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 4
• FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 4
• 208000001072 type 2 diabetes mellitus Diseases 0.000 description 4
• 230000002792 vascular Effects 0.000 description 4
• NRXZCCOHXZFHBV-UHFFFAOYSA-N (2,4,5-trifluorophenyl)methanol Chemical compound OCC1=CC(F)=C(F)C=C1F NRXZCCOHXZFHBV-UHFFFAOYSA-N 0.000 description 3
• CISBGUWMXXOYSV-SCSAIBSYSA-N (2r)-2-[(2,6-dichloropyrimidin-4-yl)amino]propan-1-ol Chemical compound OC[C@@H](C)NC1=CC(Cl)=NC(Cl)=N1 CISBGUWMXXOYSV-SCSAIBSYSA-N 0.000 description 3
• FNRUZVGFMVXMFM-RXMQYKEDSA-N (2r)-7-chloro-1,2-dimethyl-2,3-dihydroimidazo[1,2-c]pyrimidin-5-one Chemical compound C([C@H](N1C)C)N2C1=CC(Cl)=NC2=O FNRUZVGFMVXMFM-RXMQYKEDSA-N 0.000 description 3
• ZIIUUSVHCHPIQD-UHFFFAOYSA-N 2,4,6-trimethyl-N-[3-(trifluoromethyl)phenyl]benzenesulfonamide Chemical compound CC1=CC(C)=CC(C)=C1S(=O)(=O)NC1=CC=CC(C(F)(F)F)=C1 ZIIUUSVHCHPIQD-UHFFFAOYSA-N 0.000 description 3
• QPAXXIOBBIIATH-UHFFFAOYSA-N 2-(trifluoromethyl)pyrimidin-5-ol Chemical compound OC1=CN=C(C(F)(F)F)N=C1 QPAXXIOBBIIATH-UHFFFAOYSA-N 0.000 description 3
• JKGCRJJFDCFPCY-UHFFFAOYSA-N 2-[(2,6-dichloropyrimidin-4-yl)amino]-2-methylpropan-1-ol Chemical compound OCC(C)(C)NC1=CC(Cl)=NC(Cl)=N1 JKGCRJJFDCFPCY-UHFFFAOYSA-N 0.000 description 3
• INOCZFXHGQXFAL-UHFFFAOYSA-N 3-fluoro-4-(6-fluoropyridin-3-yl)oxybenzaldehyde Chemical compound C1=NC(F)=CC=C1OC1=CC=C(C=O)C=C1F INOCZFXHGQXFAL-UHFFFAOYSA-N 0.000 description 3
• ZLLDCTGRZKSLCV-UHFFFAOYSA-N 3-fluoro-4-[2-(trifluoromethyl)pyridin-4-yl]oxybenzaldehyde Chemical compound FC1=CC(C=O)=CC=C1OC1=CC=NC(C(F)(F)F)=C1 ZLLDCTGRZKSLCV-UHFFFAOYSA-N 0.000 description 3
• VNTKPYNBATZMSV-UHFFFAOYSA-N 3-fluoro-5-(trifluoromethyl)phenol Chemical compound OC1=CC(F)=CC(C(F)(F)F)=C1 VNTKPYNBATZMSV-UHFFFAOYSA-N 0.000 description 3
• JQLJBIQRTYYLGC-UHFFFAOYSA-N 4-[2-fluoro-4-(hydroxymethyl)phenoxy]-2-(trifluoromethyl)benzonitrile Chemical compound FC1=CC(CO)=CC=C1OC1=CC=C(C#N)C(C(F)(F)F)=C1 JQLJBIQRTYYLGC-UHFFFAOYSA-N 0.000 description 3
• JHOCKFVSAWCSPD-UHFFFAOYSA-N 5-(hydroxymethyl)-2-[5-(trifluoromethyl)pyridin-3-yl]oxybenzonitrile Chemical compound N#CC1=CC(CO)=CC=C1OC1=CN=CC(C(F)(F)F)=C1 JHOCKFVSAWCSPD-UHFFFAOYSA-N 0.000 description 3
• ITQBFODIUAPXPI-UHFFFAOYSA-N 7-chloro-1-cyclopropyl-2,3-dihydroimidazo[1,2-c]pyrimidin-5-one Chemical compound C1CN2C(=O)N=C(Cl)C=C2N1C1CC1 ITQBFODIUAPXPI-UHFFFAOYSA-N 0.000 description 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-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
• 102000013455 Amyloid beta-Peptides Human genes 0.000 description 3
• 108010090849 Amyloid beta-Peptides Proteins 0.000 description 3
• 206010002383 Angina Pectoris Diseases 0.000 description 3
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
• 208000000668 Chronic Pancreatitis Diseases 0.000 description 3
• 206010012289 Dementia Diseases 0.000 description 3
• 206010012438 Dermatitis atopic Diseases 0.000 description 3
• 208000010837 Diabetic eye disease Diseases 0.000 description 3
• 206010014561 Emphysema Diseases 0.000 description 3
• 206010016654 Fibrosis Diseases 0.000 description 3
• 208000007882 Gastritis Diseases 0.000 description 3
• 229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 3
• 208000023105 Huntington disease Diseases 0.000 description 3
• 206010020772 Hypertension Diseases 0.000 description 3
• 108010007622 LDL Lipoproteins Proteins 0.000 description 3
• 102000007330 LDL Lipoproteins Human genes 0.000 description 3
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 3
• 229910019142 PO4 Inorganic materials 0.000 description 3
• 206010033649 Pancreatitis chronic Diseases 0.000 description 3
• 108010064785 Phospholipases Proteins 0.000 description 3
• 102000015439 Phospholipases Human genes 0.000 description 3
• 108010058864 Phospholipases A2 Proteins 0.000 description 3
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
• NPELSDLGIFSEAU-UHFFFAOYSA-N [3,5-difluoro-4-[6-(trifluoromethyl)pyridin-3-yl]oxyphenyl]methanol Chemical compound FC1=CC(CO)=CC(F)=C1OC1=CC=C(C(F)(F)F)N=C1 NPELSDLGIFSEAU-UHFFFAOYSA-N 0.000 description 3
• NEEYXNSFUJRZAS-UHFFFAOYSA-N [4-(2-chloropyridin-4-yl)oxy-3,5-difluorophenyl]methanol Chemical compound FC1=CC(CO)=CC(F)=C1OC1=CC=NC(Cl)=C1 NEEYXNSFUJRZAS-UHFFFAOYSA-N 0.000 description 3
• YENXWOZBZJDKNJ-UHFFFAOYSA-N [4-(6-chloropyridin-3-yl)oxy-3-fluorophenyl]methanol Chemical compound FC1=CC(CO)=CC=C1OC1=CC=C(Cl)N=C1 YENXWOZBZJDKNJ-UHFFFAOYSA-N 0.000 description 3
• 230000002159 abnormal effect Effects 0.000 description 3
• 239000004480 active ingredient Substances 0.000 description 3
• 230000003110 anti-inflammatory effect Effects 0.000 description 3
• 208000007474 aortic aneurysm Diseases 0.000 description 3
• 201000008937 atopic dermatitis Diseases 0.000 description 3
• SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 3
• 210000004204 blood vessel Anatomy 0.000 description 3
• 210000004155 blood-retinal barrier Anatomy 0.000 description 3
• 230000004378 blood-retinal barrier Effects 0.000 description 3
• 230000037182 bone density Effects 0.000 description 3
• 210000002805 bone matrix Anatomy 0.000 description 3
• 239000011575 calcium Substances 0.000 description 3
• 229910052791 calcium Inorganic materials 0.000 description 3
• 239000002775 capsule Substances 0.000 description 3
• 229960001231 choline Drugs 0.000 description 3
• OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 3
• 208000023652 chronic gastritis Diseases 0.000 description 3
• 230000007882 cirrhosis Effects 0.000 description 3
• 208000019425 cirrhosis of liver Diseases 0.000 description 3
• 239000013078 crystal Substances 0.000 description 3
• 230000006378 damage Effects 0.000 description 3
• 239000003085 diluting agent Substances 0.000 description 3
• 230000006806 disease prevention Effects 0.000 description 3
• 239000007884 disintegrant Substances 0.000 description 3
• 230000004064 dysfunction Effects 0.000 description 3
• 239000000839 emulsion Substances 0.000 description 3
• 210000002889 endothelial cell Anatomy 0.000 description 3
• 238000005516 engineering process Methods 0.000 description 3
• 150000002148 esters Chemical class 0.000 description 3
• 239000000945 filler Substances 0.000 description 3
• 239000000706 filtrate Substances 0.000 description 3
• 238000003818 flash chromatography Methods 0.000 description 3
• 239000006260 foam Substances 0.000 description 3
• ASUTZQLVASHGKV-JDFRZJQESA-N galanthamine Chemical compound O1C(=C23)C(OC)=CC=C2CN(C)CC[C@]23[C@@H]1C[C@@H](O)C=C2 ASUTZQLVASHGKV-JDFRZJQESA-N 0.000 description 3
• 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 3
• 208000027866 inflammatory disease Diseases 0.000 description 3
• 239000000543 intermediate Substances 0.000 description 3
• 150000002576 ketones Chemical class 0.000 description 3
• 238000002372 labelling Methods 0.000 description 3
• 230000003902 lesion Effects 0.000 description 3
• 230000007246 mechanism Effects 0.000 description 3
• 230000001404 mediated effect Effects 0.000 description 3
• 229910052757 nitrogen Inorganic materials 0.000 description 3
• 150000005830 nonesterified fatty acids Chemical class 0.000 description 3
• 239000008184 oral solid dosage form Substances 0.000 description 3
• 210000000056 organ Anatomy 0.000 description 3
• 230000001575 pathological effect Effects 0.000 description 3
• 235000021317 phosphate Nutrition 0.000 description 3
• 235000019260 propionic acid Nutrition 0.000 description 3
• 208000004644 retinal vein occlusion Diseases 0.000 description 3
• 229920006395 saturated elastomer Polymers 0.000 description 3
• 239000012312 sodium hydride Substances 0.000 description 3
• 229910052938 sodium sulfate Inorganic materials 0.000 description 3
• 235000011152 sodium sulphate Nutrition 0.000 description 3
• 208000011580 syndromic disease Diseases 0.000 description 3
• 230000009885 systemic effect Effects 0.000 description 3
• YLJREFDVOIBQDA-UHFFFAOYSA-N tacrine Chemical compound C1=CC=C2C(N)=C(CCCC3)C3=NC2=C1 YLJREFDVOIBQDA-UHFFFAOYSA-N 0.000 description 3
• 229960001685 tacrine Drugs 0.000 description 3
• 230000001225 therapeutic effect Effects 0.000 description 3
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
• PYYIRLBSHVDFMO-SCSAIBSYSA-N (2R)-7-chloro-2-methyl-2,3-dihydro-1H-imidazo[1,2-c]pyrimidin-5-one Chemical compound ClC=1C=C2N(C(N1)=O)C[C@H](N2)C PYYIRLBSHVDFMO-SCSAIBSYSA-N 0.000 description 2
• DDKFFKLAFPRJAE-RXMQYKEDSA-N (2r)-2-[(2,6-dichloropyrimidin-4-yl)-methylamino]propan-1-ol Chemical compound OC[C@@H](C)N(C)C1=CC(Cl)=NC(Cl)=N1 DDKFFKLAFPRJAE-RXMQYKEDSA-N 0.000 description 2
• DDKFFKLAFPRJAE-YFKPBYRVSA-N (2s)-2-[(2,6-dichloropyrimidin-4-yl)-methylamino]propan-1-ol Chemical compound OC[C@H](C)N(C)C1=CC(Cl)=NC(Cl)=N1 DDKFFKLAFPRJAE-YFKPBYRVSA-N 0.000 description 2
• CISBGUWMXXOYSV-BYPYZUCNSA-N (2s)-2-[(2,6-dichloropyrimidin-4-yl)amino]propan-1-ol Chemical compound OC[C@H](C)NC1=CC(Cl)=NC(Cl)=N1 CISBGUWMXXOYSV-BYPYZUCNSA-N 0.000 description 2
• KRQHBUXUXOPOON-UHFFFAOYSA-N (3-chloro-4-fluorophenyl)methanol Chemical compound OCC1=CC=C(F)C(Cl)=C1 KRQHBUXUXOPOON-UHFFFAOYSA-N 0.000 description 2
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
• UYBWIEGTWASWSR-UHFFFAOYSA-N 1,3-diaminopropan-2-ol Chemical compound NCC(O)CN UYBWIEGTWASWSR-UHFFFAOYSA-N 0.000 description 2
• HVPQJGPSDXISJA-UHFFFAOYSA-N 1h-imidazo[1,2-c]pyrimidin-5-one Chemical compound O=C1N=CC=C2NC=CN12 HVPQJGPSDXISJA-UHFFFAOYSA-N 0.000 description 2
• WCGPCBACLBHDCI-UHFFFAOYSA-N 2,4-difluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C(F)=C1 WCGPCBACLBHDCI-UHFFFAOYSA-N 0.000 description 2
• NILKRRUKOUDYMC-UHFFFAOYSA-N 2-(3,4-difluorophenoxy)-5-(hydroxymethyl)benzonitrile Chemical compound N#CC1=CC(CO)=CC=C1OC1=CC=C(F)C(F)=C1 NILKRRUKOUDYMC-UHFFFAOYSA-N 0.000 description 2
• LDAFTDZWNFRXGG-UHFFFAOYSA-N 2-(trifluoromethyl)-1,4,5,6-tetrahydropyrimidin-5-ol Chemical compound OC1CNC(C(F)(F)F)=NC1 LDAFTDZWNFRXGG-UHFFFAOYSA-N 0.000 description 2
• FUOOLUPWFVMBKG-UHFFFAOYSA-N 2-Aminoisobutyric acid Chemical compound CC(C)(N)C(O)=O FUOOLUPWFVMBKG-UHFFFAOYSA-N 0.000 description 2
• DDKFFKLAFPRJAE-UHFFFAOYSA-N 2-[(2,6-dichloropyrimidin-4-yl)-methylamino]propan-1-ol Chemical compound OCC(C)N(C)C1=CC(Cl)=NC(Cl)=N1 DDKFFKLAFPRJAE-UHFFFAOYSA-N 0.000 description 2
• KISWVXRQTGLFGD-UHFFFAOYSA-N 2-[[2-[[6-amino-2-[[2-[[2-[[5-amino-2-[[2-[[1-[2-[[6-amino-2-[(2,5-diamino-5-oxopentanoyl)amino]hexanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]pyrrolidine-2-carbonyl]amino]-3-hydroxypropanoyl]amino]-5-oxopentanoyl]amino]-5-(diaminomethylideneamino)p Chemical compound C1CCN(C(=O)C(CCCN=C(N)N)NC(=O)C(CCCCN)NC(=O)C(N)CCC(N)=O)C1C(=O)NC(CO)C(=O)NC(CCC(N)=O)C(=O)NC(CCCN=C(N)N)C(=O)NC(CO)C(=O)NC(CCCCN)C(=O)NC(C(=O)NC(CC(C)C)C(O)=O)CC1=CC=C(O)C=C1 KISWVXRQTGLFGD-UHFFFAOYSA-N 0.000 description 2
• VBEHFOMFHUQAOW-UHFFFAOYSA-N 2-chloro-1h-pyridin-4-one Chemical compound OC1=CC=NC(Cl)=C1 VBEHFOMFHUQAOW-UHFFFAOYSA-N 0.000 description 2
• LHYBRZAQMRWQOJ-UHFFFAOYSA-N 2-methyl-2-(methylamino)propan-1-ol Chemical compound CNC(C)(C)CO LHYBRZAQMRWQOJ-UHFFFAOYSA-N 0.000 description 2
• MTTUDRPJXDRLFL-UHFFFAOYSA-N 3,5-difluoro-4-(6-fluoropyridin-3-yl)oxybenzaldehyde Chemical compound C1=NC(F)=CC=C1OC1=C(F)C=C(C=O)C=C1F MTTUDRPJXDRLFL-UHFFFAOYSA-N 0.000 description 2
• RVAVWRRHYAUVKU-UHFFFAOYSA-N 3,5-difluoro-4-[2-(trifluoromethyl)pyridin-4-yl]oxybenzaldehyde Chemical compound FC1=CC(C=O)=CC(F)=C1OC1=CC=NC(C(F)(F)F)=C1 RVAVWRRHYAUVKU-UHFFFAOYSA-N 0.000 description 2
• BYPQKRUJXCNGBW-UHFFFAOYSA-N 3,5-difluoro-4-[5-(trifluoromethyl)pyridin-3-yl]oxybenzaldehyde Chemical compound FC1=CC(C=O)=CC(F)=C1OC1=CN=CC(C(F)(F)F)=C1 BYPQKRUJXCNGBW-UHFFFAOYSA-N 0.000 description 2
• ICEBNDHTZFQTEV-UHFFFAOYSA-N 3-fluoro-4-[2-(trifluoromethyl)pyrimidin-5-yl]oxybenzaldehyde Chemical compound FC1=CC(C=O)=CC=C1OC1=CN=C(C(F)(F)F)N=C1 ICEBNDHTZFQTEV-UHFFFAOYSA-N 0.000 description 2
• JIQOINAUAHCPOM-UHFFFAOYSA-N 3-fluoro-4-[5-(trifluoromethyl)pyridin-3-yl]oxybenzaldehyde Chemical compound FC1=CC(C=O)=CC=C1OC1=CN=CC(C(F)(F)F)=C1 JIQOINAUAHCPOM-UHFFFAOYSA-N 0.000 description 2
• GKKJIQRJFFGEGR-UHFFFAOYSA-N 3-fluoro-4-[6-(trifluoromethyl)pyridin-3-yl]oxybenzaldehyde Chemical compound FC1=CC(C=O)=CC=C1OC1=CC=C(C(F)(F)F)N=C1 GKKJIQRJFFGEGR-UHFFFAOYSA-N 0.000 description 2
• TVHYRQVLUQAAOV-UHFFFAOYSA-N 3-fluoro-5-(hydroxymethyl)benzonitrile Chemical compound OCC1=CC(F)=CC(C#N)=C1 TVHYRQVLUQAAOV-UHFFFAOYSA-N 0.000 description 2
• OXCFWRVTTLSOGH-UHFFFAOYSA-N 3-phenylmethoxy-5-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CN=CC(OCC=2C=CC=CC=2)=C1 OXCFWRVTTLSOGH-UHFFFAOYSA-N 0.000 description 2
• PCSMNHYWMOMOCE-UHFFFAOYSA-N 4-(2-chloropyridin-4-yl)oxy-3,5-difluorobenzaldehyde Chemical compound FC1=CC(C=O)=CC(F)=C1OC1=CC=NC(Cl)=C1 PCSMNHYWMOMOCE-UHFFFAOYSA-N 0.000 description 2
• BLOHKKZJFXIYFN-UHFFFAOYSA-N 4-(2-chloropyridin-4-yl)oxy-3-fluorobenzaldehyde Chemical compound FC1=CC(C=O)=CC=C1OC1=CC=NC(Cl)=C1 BLOHKKZJFXIYFN-UHFFFAOYSA-N 0.000 description 2
• RIABYKNMWQIWRJ-UHFFFAOYSA-N 4-(5-chloropyridin-3-yl)oxy-3,5-difluorobenzaldehyde Chemical compound FC1=CC(C=O)=CC(F)=C1OC1=CN=CC(Cl)=C1 RIABYKNMWQIWRJ-UHFFFAOYSA-N 0.000 description 2
• YLBAYWZRAYNYLH-UHFFFAOYSA-N 4-(6-chloropyridin-3-yl)oxy-3,5-difluorobenzaldehyde Chemical compound FC1=CC(C=O)=CC(F)=C1OC1=CC=C(Cl)N=C1 YLBAYWZRAYNYLH-UHFFFAOYSA-N 0.000 description 2
• 229960000549 4-dimethylaminophenol Drugs 0.000 description 2
• YLSOMBNWTNQJJO-UHFFFAOYSA-N 5-(hydroxymethyl)-2-[3-(trifluoromethyl)phenoxy]benzonitrile Chemical compound N#CC1=CC(CO)=CC=C1OC1=CC=CC(C(F)(F)F)=C1 YLSOMBNWTNQJJO-UHFFFAOYSA-N 0.000 description 2
• JAHVMNLMQSLVNQ-UHFFFAOYSA-N 6-chloro-4-[1-hydroxypropan-2-yl(methyl)amino]-1h-pyrimidin-2-one Chemical compound OCC(C)N(C)C1=CC(Cl)=NC(=O)N1 JAHVMNLMQSLVNQ-UHFFFAOYSA-N 0.000 description 2
• JAHVMNLMQSLVNQ-RXMQYKEDSA-N 6-chloro-4-[[(2r)-1-hydroxypropan-2-yl]-methylamino]-1h-pyrimidin-2-one Chemical compound OC[C@@H](C)N(C)C1=CC(Cl)=NC(=O)N1 JAHVMNLMQSLVNQ-RXMQYKEDSA-N 0.000 description 2
• JAHVMNLMQSLVNQ-YFKPBYRVSA-N 6-chloro-4-[[(2s)-1-hydroxypropan-2-yl]-methylamino]-1h-pyrimidin-2-one Chemical compound OC[C@H](C)N(C)C1=CC(Cl)=NC(=O)N1 JAHVMNLMQSLVNQ-YFKPBYRVSA-N 0.000 description 2
• KVCOOWROABTXDJ-UHFFFAOYSA-N 6-chloropyridin-3-ol Chemical compound OC1=CC=C(Cl)N=C1 KVCOOWROABTXDJ-UHFFFAOYSA-N 0.000 description 2
• HTRLNWYWOKWCLV-UHFFFAOYSA-N 6-fluoropyridin-3-ol Chemical compound OC1=CC=C(F)N=C1 HTRLNWYWOKWCLV-UHFFFAOYSA-N 0.000 description 2
• TWFJFNDXCRKLBS-UHFFFAOYSA-N 7-chloro-2,3-dihydro-1H-imidazo[1,2-c]pyrimidin-5-one Chemical compound O=C1N=C(Cl)C=C2NCCN21 TWFJFNDXCRKLBS-UHFFFAOYSA-N 0.000 description 2
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
• 102100040214 Apolipoprotein(a) Human genes 0.000 description 2
• 101710115418 Apolipoprotein(a) Proteins 0.000 description 2
• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
• 208000037260 Atherosclerotic Plaque Diseases 0.000 description 2
• 208000023275 Autoimmune disease Diseases 0.000 description 2
• 208000002177 Cataract Diseases 0.000 description 2
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 2
• KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
• 229920002261 Corn starch Polymers 0.000 description 2
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
• 206010013786 Dry skin Diseases 0.000 description 2
• 208000032928 Dyslipidaemia Diseases 0.000 description 2
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
• 101000983077 Homo sapiens Phospholipase A2 Proteins 0.000 description 2
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
• 102000004157 Hydrolases Human genes 0.000 description 2
• 108090000604 Hydrolases Proteins 0.000 description 2
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
• 206010061216 Infarction Diseases 0.000 description 2
• 206010022489 Insulin Resistance Diseases 0.000 description 2
• 229940122355 Insulin sensitizer Drugs 0.000 description 2
• QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 2
• 208000017170 Lipid metabolism disease Diseases 0.000 description 2
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
• OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 2
• 208000001145 Metabolic Syndrome Diseases 0.000 description 2
• 229920000168 Microcrystalline cellulose Polymers 0.000 description 2
• 229920000881 Modified starch Polymers 0.000 description 2
• PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 description 2
• WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
• 208000036110 Neuroinflammatory disease Diseases 0.000 description 2
• 208000002193 Pain Diseases 0.000 description 2
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
• 206010063837 Reperfusion injury Diseases 0.000 description 2
• XSVMFMHYUFZWBK-NSHDSACASA-N Rivastigmine Chemical compound CCN(C)C(=O)OC1=CC=CC([C@H](C)N(C)C)=C1 XSVMFMHYUFZWBK-NSHDSACASA-N 0.000 description 2
• YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 description 2
• 206010040047 Sepsis Diseases 0.000 description 2
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 2
• VAQYTEMRYIRPAN-UHFFFAOYSA-N [3,5-difluoro-4-(6-fluoropyridin-3-yl)oxyphenyl]methanol Chemical compound FC1=CC(CO)=CC(F)=C1OC1=CC=C(F)N=C1 VAQYTEMRYIRPAN-UHFFFAOYSA-N 0.000 description 2
• UIJSDZNSJBJXRJ-UHFFFAOYSA-N [3,5-difluoro-4-[2-(trifluoromethyl)pyrimidin-5-yl]oxyphenyl]methanol Chemical compound FC1=CC(CO)=CC(F)=C1OC1=CN=C(C(F)(F)F)N=C1 UIJSDZNSJBJXRJ-UHFFFAOYSA-N 0.000 description 2
• OYQQBKFKXHCTNG-UHFFFAOYSA-N [3-fluoro-4-(2-fluoropyridin-4-yl)oxyphenyl]methanol Chemical compound FC1=CC(CO)=CC=C1OC1=CC=NC(F)=C1 OYQQBKFKXHCTNG-UHFFFAOYSA-N 0.000 description 2
• KXMXFCRWBSCWRJ-UHFFFAOYSA-N [3-fluoro-4-(3-fluorophenoxy)phenyl]methanol Chemical compound FC1=CC(CO)=CC=C1OC1=CC=CC(F)=C1 KXMXFCRWBSCWRJ-UHFFFAOYSA-N 0.000 description 2
• CTUITKMAAHFDLH-UHFFFAOYSA-N [3-fluoro-4-(4-fluorophenoxy)phenyl]methanol Chemical compound FC1=CC(CO)=CC=C1OC1=CC=C(F)C=C1 CTUITKMAAHFDLH-UHFFFAOYSA-N 0.000 description 2
• UTXPGEVPQDYUGQ-UHFFFAOYSA-N [3-fluoro-4-(6-fluoropyridin-3-yl)oxyphenyl]methanol Chemical compound FC1=CC(CO)=CC=C1OC1=CC=C(F)N=C1 UTXPGEVPQDYUGQ-UHFFFAOYSA-N 0.000 description 2
• WQVFYLCVJUWVGI-UHFFFAOYSA-N [4-(2-chloropyridin-4-yl)oxy-3-fluorophenyl]methanol Chemical compound FC1=CC(CO)=CC=C1OC1=CC=NC(Cl)=C1 WQVFYLCVJUWVGI-UHFFFAOYSA-N 0.000 description 2
• MGYDTAFWCFTDCM-UHFFFAOYSA-N [4-(5-chloropyridin-3-yl)oxy-3,5-difluorophenyl]methanol Chemical compound FC1=CC(CO)=CC(F)=C1OC1=CN=CC(Cl)=C1 MGYDTAFWCFTDCM-UHFFFAOYSA-N 0.000 description 2
• INLWEFRUKYGJDJ-UHFFFAOYSA-N [4-(5-chloropyridin-3-yl)oxy-3-fluorophenyl]methanol Chemical compound FC1=CC(CO)=CC=C1OC1=CN=CC(Cl)=C1 INLWEFRUKYGJDJ-UHFFFAOYSA-N 0.000 description 2
• FFBOPXNVXTYBKB-UHFFFAOYSA-N [4-(6-chloropyridin-3-yl)oxy-3,5-difluorophenyl]methanol Chemical compound FC1=CC(CO)=CC(F)=C1OC1=CC=C(Cl)N=C1 FFBOPXNVXTYBKB-UHFFFAOYSA-N 0.000 description 2
• 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 description 2
• 230000005856 abnormality Effects 0.000 description 2
• 230000004913 activation Effects 0.000 description 2
• 208000038016 acute inflammation Diseases 0.000 description 2
• 230000006022 acute inflammation Effects 0.000 description 2
• 235000010443 alginic acid Nutrition 0.000 description 2
• 239000000783 alginic acid Substances 0.000 description 2
• 229920000615 alginic acid Polymers 0.000 description 2
• 229960001126 alginic acid Drugs 0.000 description 2
• 150000004781 alginic acids Chemical class 0.000 description 2
• 150000001335 aliphatic alkanes Chemical class 0.000 description 2
• 229910052782 aluminium Inorganic materials 0.000 description 2
• XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
• 239000003963 antioxidant agent Substances 0.000 description 2
• 235000006708 antioxidants Nutrition 0.000 description 2
• 239000007864 aqueous solution Substances 0.000 description 2
• 229940039856 aricept Drugs 0.000 description 2
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
• HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
• 230000004071 biological effect Effects 0.000 description 2
• 230000037396 body weight Effects 0.000 description 2
• 210000001185 bone marrow Anatomy 0.000 description 2
• 210000005013 brain tissue Anatomy 0.000 description 2
• 125000001246 bromo group Chemical group Br* 0.000 description 2
• 230000002308 calcification Effects 0.000 description 2
• OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
• 210000004027 cell Anatomy 0.000 description 2
• 208000026106 cerebrovascular disease Diseases 0.000 description 2
• 125000001309 chloro group Chemical group Cl* 0.000 description 2
• 208000037976 chronic inflammation Diseases 0.000 description 2
• 230000006020 chronic inflammation Effects 0.000 description 2
• 230000003920 cognitive function Effects 0.000 description 2
• 229940125898 compound 5 Drugs 0.000 description 2
• 239000012141 concentrate Substances 0.000 description 2
• 235000008504 concentrate Nutrition 0.000 description 2
• 238000007796 conventional method Methods 0.000 description 2
• 239000008120 corn starch Substances 0.000 description 2
• 208000029078 coronary artery disease Diseases 0.000 description 2
• ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
• PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
• 230000001419 dependent effect Effects 0.000 description 2
• 238000001514 detection method Methods 0.000 description 2
• 238000011161 development Methods 0.000 description 2
• 230000018109 developmental process Effects 0.000 description 2
• 150000004141 diterpene derivatives Chemical class 0.000 description 2
• 230000037336 dry skin Effects 0.000 description 2
• 229940011871 estrogen Drugs 0.000 description 2
• 239000000262 estrogen Substances 0.000 description 2
• CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 2
• 239000000796 flavoring agent Substances 0.000 description 2
• 239000011737 fluorine Substances 0.000 description 2
• 238000002657 hormone replacement therapy Methods 0.000 description 2
• 239000001257 hydrogen Substances 0.000 description 2
• 230000007062 hydrolysis Effects 0.000 description 2
• 238000006460 hydrolysis reaction Methods 0.000 description 2
• 238000002649 immunization Methods 0.000 description 2
• 238000011065 in-situ storage Methods 0.000 description 2
• 239000004615 ingredient Substances 0.000 description 2
• 230000003993 interaction Effects 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
• FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 2
• 230000002366 lipolytic effect Effects 0.000 description 2
• 229910052744 lithium Inorganic materials 0.000 description 2
• 229960004844 lovastatin Drugs 0.000 description 2
• PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 description 2
• QLJODMDSTUBWDW-UHFFFAOYSA-N lovastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 QLJODMDSTUBWDW-UHFFFAOYSA-N 0.000 description 2
• 239000007937 lozenge Substances 0.000 description 2
• 239000000314 lubricant Substances 0.000 description 2
• 239000011777 magnesium Substances 0.000 description 2
• 229910052749 magnesium Inorganic materials 0.000 description 2
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
• BUGYDGFZZOZRHP-UHFFFAOYSA-N memantine Chemical compound C1C(C2)CC3(C)CC1(C)CC2(N)C3 BUGYDGFZZOZRHP-UHFFFAOYSA-N 0.000 description 2
• 229960004640 memantine Drugs 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
• OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 2
• QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
• 229940016286 microcrystalline cellulose Drugs 0.000 description 2
• 239000008108 microcrystalline cellulose Substances 0.000 description 2
• 235000019813 microcrystalline cellulose Nutrition 0.000 description 2
• 230000006724 microglial activation Effects 0.000 description 2
• HFYGCOINAADNEW-UHFFFAOYSA-N n-(2-bromoethyl)-2,6-dichloropyrimidin-4-amine Chemical compound ClC1=CC(NCCBr)=NC(Cl)=N1 HFYGCOINAADNEW-UHFFFAOYSA-N 0.000 description 2
• 210000005036 nerve Anatomy 0.000 description 2
• 230000003959 neuroinflammation Effects 0.000 description 2
• LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
• 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 2
• QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
• 239000012074 organic phase Substances 0.000 description 2
• 239000001301 oxygen Substances 0.000 description 2
• 229910052760 oxygen Inorganic materials 0.000 description 2
• 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 2
• 230000002093 peripheral effect Effects 0.000 description 2
• 229960005095 pioglitazone Drugs 0.000 description 2
• 239000011591 potassium Substances 0.000 description 2
• 229910052700 potassium Inorganic materials 0.000 description 2
• 229920001592 potato starch Polymers 0.000 description 2
• 238000012746 preparative thin layer chromatography Methods 0.000 description 2
• 230000000770 proinflammatory effect Effects 0.000 description 2
• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
• 239000003642 reactive oxygen metabolite Substances 0.000 description 2
• 238000003753 real-time PCR Methods 0.000 description 2
• 230000009467 reduction Effects 0.000 description 2
• 230000010410 reperfusion Effects 0.000 description 2
• 210000001525 retina Anatomy 0.000 description 2
• 230000002207 retinal effect Effects 0.000 description 2
• 229960000672 rosuvastatin Drugs 0.000 description 2
• BPRHUIZQVSMCRT-VEUZHWNKSA-N rosuvastatin Chemical compound CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC(O)=O BPRHUIZQVSMCRT-VEUZHWNKSA-N 0.000 description 2
• YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 2
• 239000000523 sample Substances 0.000 description 2
• 201000000980 schizophrenia Diseases 0.000 description 2
• 235000015424 sodium Nutrition 0.000 description 2
• 229910052708 sodium Inorganic materials 0.000 description 2
• TYOXFGCYGAZCMI-ZETCQYMHSA-N tert-butyl (2s)-7-chloro-2-methyl-5-oxo-2,3-dihydroimidazo[1,2-c]pyrimidine-1-carboxylate Chemical compound C([C@@H](N1C(=O)OC(C)(C)C)C)N2C1=CC(Cl)=NC2=O TYOXFGCYGAZCMI-ZETCQYMHSA-N 0.000 description 2
• 150000003573 thiols Chemical class 0.000 description 2
• 239000003981 vehicle Substances 0.000 description 2
• 239000003643 water by type Substances 0.000 description 2
• 230000029663 wound healing Effects 0.000 description 2
• KIKCAPPVFQLOIU-UHFFFAOYSA-N (2,5-difluorophenyl)methanol Chemical compound OCC1=CC(F)=CC=C1F KIKCAPPVFQLOIU-UHFFFAOYSA-N 0.000 description 1
• PXWASTUQOKUFKY-SCSAIBSYSA-N (2r)-2-(methylamino)propan-1-ol Chemical compound CN[C@H](C)CO PXWASTUQOKUFKY-SCSAIBSYSA-N 0.000 description 1
• BKMMTJMQCTUHRP-GSVOUGTGSA-N (2r)-2-aminopropan-1-ol Chemical compound C[C@@H](N)CO BKMMTJMQCTUHRP-GSVOUGTGSA-N 0.000 description 1
• WVQCPCLYVMDRFB-SNVBAGLBSA-N (2r)-7-[[3,5-difluoro-4-[2-(trifluoromethyl)pyridin-4-yl]oxyphenyl]methoxy]-2-methyl-2,3-dihydro-1h-imidazo[1,2-c]pyrimidin-5-one Chemical compound C([C@H](N1)C)N(C(N=2)=O)C1=CC=2OCC(C=C1F)=CC(F)=C1OC1=CC=NC(C(F)(F)F)=C1 WVQCPCLYVMDRFB-SNVBAGLBSA-N 0.000 description 1
• KKBHQSCFKCFRIJ-GFCCVEGCSA-N (2r)-7-[[3-fluoro-4-[2-(trifluoromethyl)pyridin-4-yl]oxyphenyl]methoxy]-1,2-dimethyl-2,3-dihydroimidazo[1,2-c]pyrimidin-5-one Chemical compound C([C@H](N1C)C)N(C(N=2)=O)C1=CC=2OCC(C=C1F)=CC=C1OC1=CC=NC(C(F)(F)F)=C1 KKBHQSCFKCFRIJ-GFCCVEGCSA-N 0.000 description 1
• YGBHDTFUSJNOCI-GFCCVEGCSA-N (2r)-7-[[3-fluoro-4-[6-(trifluoromethyl)pyridin-3-yl]oxyphenyl]methoxy]-1,2-dimethyl-2,3-dihydroimidazo[1,2-c]pyrimidin-5-one Chemical compound C([C@H](N1C)C)N(C(N=2)=O)C1=CC=2OCC(C=C1F)=CC=C1OC1=CC=C(C(F)(F)F)N=C1 YGBHDTFUSJNOCI-GFCCVEGCSA-N 0.000 description 1
• DTZWOPNOXQYNKH-QMMMGPOBSA-N (2s)-7-[(3,4-difluorophenyl)methoxy]-2-methyl-2,3-dihydro-1h-imidazo[1,2-c]pyrimidin-5-one Chemical compound C([C@@H](N1)C)N(C(N=2)=O)C1=CC=2OCC1=CC=C(F)C(F)=C1 DTZWOPNOXQYNKH-QMMMGPOBSA-N 0.000 description 1
• CTMXQTBDWBDNGT-QMMMGPOBSA-N (2s)-7-[(3,5-difluorophenyl)methoxy]-2-methyl-2,3-dihydro-1h-imidazo[1,2-c]pyrimidin-5-one Chemical compound C([C@@H](N1)C)N(C(N=2)=O)C1=CC=2OCC1=CC(F)=CC(F)=C1 CTMXQTBDWBDNGT-QMMMGPOBSA-N 0.000 description 1
• JFHZQFATRYMMQC-LBPRGKRZSA-N (2s)-7-[[3,5-difluoro-4-(3-fluorophenoxy)phenyl]methoxy]-1,2-dimethyl-2,3-dihydroimidazo[1,2-c]pyrimidin-5-one Chemical compound C([C@@H](N1C)C)N(C(N=2)=O)C1=CC=2OCC(C=C1F)=CC(F)=C1OC1=CC=CC(F)=C1 JFHZQFATRYMMQC-LBPRGKRZSA-N 0.000 description 1
• WVQCPCLYVMDRFB-JTQLQIEISA-N (2s)-7-[[3,5-difluoro-4-[2-(trifluoromethyl)pyridin-4-yl]oxyphenyl]methoxy]-2-methyl-2,3-dihydro-1h-imidazo[1,2-c]pyrimidin-5-one Chemical compound C([C@@H](N1)C)N(C(N=2)=O)C1=CC=2OCC(C=C1F)=CC(F)=C1OC1=CC=NC(C(F)(F)F)=C1 WVQCPCLYVMDRFB-JTQLQIEISA-N 0.000 description 1
• DCGQCFBCCBEGQG-JTQLQIEISA-N (2s)-7-[[3,5-difluoro-4-[6-(trifluoromethyl)pyridin-3-yl]oxyphenyl]methoxy]-2-methyl-2,3-dihydro-1h-imidazo[1,2-c]pyrimidin-5-one Chemical compound C([C@@H](N1)C)N(C(N=2)=O)C1=CC=2OCC(C=C1F)=CC(F)=C1OC1=CC=C(C(F)(F)F)N=C1 DCGQCFBCCBEGQG-JTQLQIEISA-N 0.000 description 1
• ZENANMMNCZMDLS-ZDUSSCGKSA-N (2s)-7-[[3-fluoro-4-(3-fluorophenoxy)phenyl]methoxy]-1,2-dimethyl-2,3-dihydroimidazo[1,2-c]pyrimidin-5-one Chemical compound C([C@@H](N1C)C)N(C(N=2)=O)C1=CC=2OCC(C=C1F)=CC=C1OC1=CC=CC(F)=C1 ZENANMMNCZMDLS-ZDUSSCGKSA-N 0.000 description 1
• BOTFWXOJFHJABZ-LBPRGKRZSA-N (2s)-7-[[3-fluoro-4-(3-fluorophenoxy)phenyl]methoxy]-2-methyl-2,3-dihydro-1h-imidazo[1,2-c]pyrimidin-5-one Chemical compound C([C@@H](N1)C)N(C(N=2)=O)C1=CC=2OCC(C=C1F)=CC=C1OC1=CC=CC(F)=C1 BOTFWXOJFHJABZ-LBPRGKRZSA-N 0.000 description 1
• IWHPIXDIFYULNL-ZDUSSCGKSA-N (2s)-7-[[3-fluoro-4-(4-fluorophenoxy)phenyl]methoxy]-1,2-dimethyl-2,3-dihydroimidazo[1,2-c]pyrimidin-5-one Chemical compound C([C@@H](N1C)C)N(C(N=2)=O)C1=CC=2OCC(C=C1F)=CC=C1OC1=CC=C(F)C=C1 IWHPIXDIFYULNL-ZDUSSCGKSA-N 0.000 description 1
• KKBHQSCFKCFRIJ-LBPRGKRZSA-N (2s)-7-[[3-fluoro-4-[2-(trifluoromethyl)pyridin-4-yl]oxyphenyl]methoxy]-1,2-dimethyl-2,3-dihydroimidazo[1,2-c]pyrimidin-5-one Chemical compound C([C@@H](N1C)C)N(C(N=2)=O)C1=CC=2OCC(C=C1F)=CC=C1OC1=CC=NC(C(F)(F)F)=C1 KKBHQSCFKCFRIJ-LBPRGKRZSA-N 0.000 description 1
• WRPMXEMENIGVPU-NSHDSACASA-N (2s)-7-[[3-fluoro-4-[2-(trifluoromethyl)pyridin-4-yl]oxyphenyl]methoxy]-2-methyl-2,3-dihydro-1h-imidazo[1,2-c]pyrimidin-5-one Chemical compound C([C@@H](N1)C)N(C(N=2)=O)C1=CC=2OCC(C=C1F)=CC=C1OC1=CC=NC(C(F)(F)F)=C1 WRPMXEMENIGVPU-NSHDSACASA-N 0.000 description 1
• KYZYHUUPXYKTBU-NSHDSACASA-N (2s)-7-[[3-fluoro-4-[2-(trifluoromethyl)pyrimidin-5-yl]oxyphenyl]methoxy]-1,2-dimethyl-2,3-dihydroimidazo[1,2-c]pyrimidin-5-one Chemical compound C([C@@H](N1C)C)N(C(N=2)=O)C1=CC=2OCC(C=C1F)=CC=C1OC1=CN=C(C(F)(F)F)N=C1 KYZYHUUPXYKTBU-NSHDSACASA-N 0.000 description 1
• HAILHAHKJQDAFA-LBPRGKRZSA-N (2s)-7-[[3-fluoro-4-[5-(trifluoromethyl)pyridin-3-yl]oxyphenyl]methoxy]-1,2-dimethyl-2,3-dihydroimidazo[1,2-c]pyrimidin-5-one Chemical compound C([C@@H](N1C)C)N(C(N=2)=O)C1=CC=2OCC(C=C1F)=CC=C1OC1=CN=CC(C(F)(F)F)=C1 HAILHAHKJQDAFA-LBPRGKRZSA-N 0.000 description 1
• YGBHDTFUSJNOCI-LBPRGKRZSA-N (2s)-7-[[3-fluoro-4-[6-(trifluoromethyl)pyridin-3-yl]oxyphenyl]methoxy]-1,2-dimethyl-2,3-dihydroimidazo[1,2-c]pyrimidin-5-one Chemical compound C([C@@H](N1C)C)N(C(N=2)=O)C1=CC=2OCC(C=C1F)=CC=C1OC1=CC=C(C(F)(F)F)N=C1 YGBHDTFUSJNOCI-LBPRGKRZSA-N 0.000 description 1
• HURXRJUAPOVLSL-NSHDSACASA-N (2s)-7-[[3-fluoro-4-[6-(trifluoromethyl)pyridin-3-yl]oxyphenyl]methoxy]-2-methyl-2,3-dihydro-1h-imidazo[1,2-c]pyrimidin-5-one Chemical compound C([C@@H](N1)C)N(C(N=2)=O)C1=CC=2OCC(C=C1F)=CC=C1OC1=CC=C(C(F)(F)F)N=C1 HURXRJUAPOVLSL-NSHDSACASA-N 0.000 description 1
• ZQHYZSBCAMPSCZ-NSHDSACASA-N (2s)-7-[[4-(3,4-difluorophenoxy)-3,5-difluorophenyl]methoxy]-1,2-dimethyl-2,3-dihydroimidazo[1,2-c]pyrimidin-5-one Chemical compound C([C@@H](N1C)C)N(C(N=2)=O)C1=CC=2OCC(C=C1F)=CC(F)=C1OC1=CC=C(F)C(F)=C1 ZQHYZSBCAMPSCZ-NSHDSACASA-N 0.000 description 1
• ZZUIAJBJEXERST-LBPRGKRZSA-N (2s)-7-[[4-(5-chloropyridin-3-yl)oxy-3-fluorophenyl]methoxy]-1,2-dimethyl-2,3-dihydroimidazo[1,2-c]pyrimidin-5-one Chemical compound C([C@@H](N1C)C)N(C(N=2)=O)C1=CC=2OCC(C=C1F)=CC=C1OC1=CN=CC(Cl)=C1 ZZUIAJBJEXERST-LBPRGKRZSA-N 0.000 description 1
• HWETYUFGGOHKCA-LURJTMIESA-N (2s)-7-chloro-1-ethyl-2-methyl-2,3-dihydroimidazo[1,2-c]pyrimidin-5-one Chemical compound C([C@H](C)N1CC)N2C1=CC(Cl)=NC2=O HWETYUFGGOHKCA-LURJTMIESA-N 0.000 description 1
• NVVIQVPWALTFMC-ZETCQYMHSA-N (2s)-7-chloro-2-methyl-1-propan-2-yl-2,3-dihydroimidazo[1,2-c]pyrimidin-5-one Chemical compound C([C@H](C)N1C(C)C)N2C1=CC(Cl)=NC2=O NVVIQVPWALTFMC-ZETCQYMHSA-N 0.000 description 1
• VJTJBAMDTCIMOB-UHFFFAOYSA-N (3-chloro-5-fluorophenyl)methanol Chemical compound OCC1=CC(F)=CC(Cl)=C1 VJTJBAMDTCIMOB-UHFFFAOYSA-N 0.000 description 1
• ZSRDNPVYGSFUMD-UHFFFAOYSA-N (3-chlorophenyl)methanol Chemical compound OCC1=CC=CC(Cl)=C1 ZSRDNPVYGSFUMD-UHFFFAOYSA-N 0.000 description 1
• ZGGHKIMDNBDHJB-NRFPMOEYSA-M (3R,5S)-fluvastatin sodium Chemical compound [Na+].C12=CC=CC=C2N(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 ZGGHKIMDNBDHJB-NRFPMOEYSA-M 0.000 description 1
• MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 description 1
• JEAFLVNESBTMPU-UHFFFAOYSA-N (4-chloro-3-fluorophenyl)methanol Chemical compound OCC1=CC=C(Cl)C(F)=C1 JEAFLVNESBTMPU-UHFFFAOYSA-N 0.000 description 1
• BKMMTJMQCTUHRP-VKHMYHEASA-N (S)-2-aminopropan-1-ol Chemical compound C[C@H](N)CO BKMMTJMQCTUHRP-VKHMYHEASA-N 0.000 description 1
• QZLINQZBUKTXIZ-BQYQJAHWSA-N (e)-1-(4-nitrophenyl)-3-thiophen-2-ylprop-2-en-1-one Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(=O)\C=C\C1=CC=CS1 QZLINQZBUKTXIZ-BQYQJAHWSA-N 0.000 description 1
• UWYVPFMHMJIBHE-OWOJBTEDSA-N (e)-2-hydroxybut-2-enedioic acid Chemical compound OC(=O)\C=C(\O)C(O)=O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
• PFKFTWBEEFSNDU-UHFFFAOYSA-N 1,1'-Carbonyldiimidazole Substances C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
• KXSXRQBEWPXLQR-UHFFFAOYSA-N 1,2,2-trimethyl-7-(2-thiophen-2-ylethoxy)-3h-imidazo[1,2-c]pyrimidin-5-one Chemical compound N=1C(=O)N2CC(C)(C)N(C)C2=CC=1OCCC1=CC=CS1 KXSXRQBEWPXLQR-UHFFFAOYSA-N 0.000 description 1
• DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical compound CNNC DIIIISSCIXVANO-UHFFFAOYSA-N 0.000 description 1
• TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 description 1
• YGIABALXNBVHBX-UHFFFAOYSA-N 1-[4-[7-(diethylamino)-4-methyl-2-oxochromen-3-yl]phenyl]pyrrole-2,5-dione Chemical compound O=C1OC2=CC(N(CC)CC)=CC=C2C(C)=C1C(C=C1)=CC=C1N1C(=O)C=CC1=O YGIABALXNBVHBX-UHFFFAOYSA-N 0.000 description 1
• UGJYZZNMPRHVGY-UHFFFAOYSA-N 1-cyclopropyl-7-[(3,4-difluorophenyl)methoxy]-2,3-dihydroimidazo[1,2-c]pyrimidin-5-one Chemical compound C1=C(F)C(F)=CC=C1COC1=NC(=O)N2CCN(C3CC3)C2=C1 UGJYZZNMPRHVGY-UHFFFAOYSA-N 0.000 description 1
• IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
• JLZVIWSFUPLSOR-UHFFFAOYSA-N 2,3-difluorobenzoic acid Chemical compound OC(=O)C1=CC=CC(F)=C1F JLZVIWSFUPLSOR-UHFFFAOYSA-N 0.000 description 1
• HCSBTDBGTNZOAB-UHFFFAOYSA-N 2,3-dinitrobenzoic acid Chemical compound OC(=O)C1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O HCSBTDBGTNZOAB-UHFFFAOYSA-N 0.000 description 1
• GIKMWFAAEIACRF-UHFFFAOYSA-N 2,4,5-trichloropyrimidine Chemical compound ClC1=NC=C(Cl)C(Cl)=N1 GIKMWFAAEIACRF-UHFFFAOYSA-N 0.000 description 1
• AKAMNXFLKYKFOJ-UHFFFAOYSA-N 2,4,5-trifluorobenzoic acid Chemical compound OC(=O)C1=CC(F)=C(F)C=C1F AKAMNXFLKYKFOJ-UHFFFAOYSA-N 0.000 description 1
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 1
• RBNNHALDGIKSBZ-UHFFFAOYSA-N 2-(2,3-difluorophenyl)ethanol Chemical compound OCCC1=CC=CC(F)=C1F RBNNHALDGIKSBZ-UHFFFAOYSA-N 0.000 description 1
• LQIZHIYYOQHWNF-UHFFFAOYSA-N 2-(3,4-difluorophenyl)ethanol Chemical compound OCCC1=CC=C(F)C(F)=C1 LQIZHIYYOQHWNF-UHFFFAOYSA-N 0.000 description 1
• XDZLMMDJKWJEJF-UHFFFAOYSA-N 2-(3,5-difluorophenyl)ethanol Chemical compound OCCC1=CC(F)=CC(F)=C1 XDZLMMDJKWJEJF-UHFFFAOYSA-N 0.000 description 1
• GRGKJAFNGFGJND-UHFFFAOYSA-N 2-(4-fluorophenoxy)-5-(hydroxymethyl)benzonitrile Chemical compound N#CC1=CC(CO)=CC=C1OC1=CC=C(F)C=C1 GRGKJAFNGFGJND-UHFFFAOYSA-N 0.000 description 1
• BXGYYDRIMBPOMN-UHFFFAOYSA-N 2-(hydroxymethoxy)ethoxymethanol Chemical compound OCOCCOCO BXGYYDRIMBPOMN-UHFFFAOYSA-N 0.000 description 1
• VGHCSARTLMMHGM-UHFFFAOYSA-N 2-(trifluoromethyl)pyran-4-one Chemical compound FC(F)(F)C1=CC(=O)C=CO1 VGHCSARTLMMHGM-UHFFFAOYSA-N 0.000 description 1
• HVAUUPRFYPCOCA-AREMUKBSSA-N 2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCOC[C@@H](OC(C)=O)COP([O-])(=O)OCC[N+](C)(C)C HVAUUPRFYPCOCA-AREMUKBSSA-N 0.000 description 1
• WKMJQCYXSPQJGZ-UHFFFAOYSA-N 2-[(2,6-dichloropyrimidin-4-yl)-methylamino]-2-methylpropan-1-ol Chemical compound OCC(C)(C)N(C)C1=CC(Cl)=NC(Cl)=N1 WKMJQCYXSPQJGZ-UHFFFAOYSA-N 0.000 description 1
• YHYBYXWADBYJNE-UHFFFAOYSA-N 2-[3-fluoro-5-(trifluoromethyl)phenoxy]-5-(hydroxymethyl)benzonitrile Chemical compound N#CC1=CC(CO)=CC=C1OC1=CC(F)=CC(C(F)(F)F)=C1 YHYBYXWADBYJNE-UHFFFAOYSA-N 0.000 description 1
• VCULWHCSUAEOPR-UHFFFAOYSA-N 2-chloro-5-[2-fluoro-4-(hydroxymethyl)phenoxy]benzonitrile Chemical compound FC1=CC(CO)=CC=C1OC1=CC=C(Cl)C(C#N)=C1 VCULWHCSUAEOPR-UHFFFAOYSA-N 0.000 description 1
• JEXQWCBPEWHFKC-UHFFFAOYSA-N 2-cyclopentylethanol Chemical compound OCCC1CCCC1 JEXQWCBPEWHFKC-UHFFFAOYSA-N 0.000 description 1
• BRLSDLHMGRDAPF-UHFFFAOYSA-N 2-fluoro-1h-pyridin-4-one Chemical compound FC1=CC(=O)C=CN1 BRLSDLHMGRDAPF-UHFFFAOYSA-N 0.000 description 1
• HUDVCPBUHRBSJJ-VIFPVBQESA-N 2-fluoro-5-[[(2s)-2-methyl-5-oxo-2,3-dihydro-1h-imidazo[1,2-c]pyrimidin-7-yl]oxymethyl]benzonitrile Chemical compound C([C@@H](N1)C)N(C(N=2)=O)C1=CC=2OCC1=CC=C(F)C(C#N)=C1 HUDVCPBUHRBSJJ-VIFPVBQESA-N 0.000 description 1
• FWKGOPOAFONVCR-UHFFFAOYSA-N 2-fluoro-5-methylsulfanylbenzonitrile Chemical compound CSC1=CC=C(F)C(C#N)=C1 FWKGOPOAFONVCR-UHFFFAOYSA-N 0.000 description 1
• VMJOFTHFJMLIKL-UHFFFAOYSA-N 2-thiophen-2-ylethanol Chemical compound OCCC1=CC=CS1 VMJOFTHFJMLIKL-UHFFFAOYSA-N 0.000 description 1
• 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 description 1
• OMRCXTBFBBWTDL-UHFFFAOYSA-N 3-chloro-5-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CN=CC(Cl)=C1 OMRCXTBFBBWTDL-UHFFFAOYSA-N 0.000 description 1
• JMHGATOBRPWPBZ-UHFFFAOYSA-N 3-cyano-4-fluorobenzoic acid Chemical compound OC(=O)C1=CC=C(F)C(C#N)=C1 JMHGATOBRPWPBZ-UHFFFAOYSA-N 0.000 description 1
• SRUMDQQNHCQNPK-UHFFFAOYSA-N 3-fluoro-4-(2-fluoropyridin-4-yl)oxybenzaldehyde Chemical compound C1=NC(F)=CC(OC=2C(=CC(C=O)=CC=2)F)=C1 SRUMDQQNHCQNPK-UHFFFAOYSA-N 0.000 description 1
• UXWXSKWBTIWJBS-UHFFFAOYSA-N 3-fluoro-4-[3-fluoro-5-(trifluoromethyl)phenoxy]benzaldehyde Chemical compound FC(F)(F)C1=CC(F)=CC(OC=2C(=CC(C=O)=CC=2)F)=C1 UXWXSKWBTIWJBS-UHFFFAOYSA-N 0.000 description 1
• GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-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
• SARWFCJKACMAIQ-UHFFFAOYSA-N 4-(6-chloropyridin-3-yl)oxy-3-fluorobenzaldehyde Chemical compound FC1=CC(C=O)=CC=C1OC1=CC=C(Cl)N=C1 SARWFCJKACMAIQ-UHFFFAOYSA-N 0.000 description 1
• HVBSAKJJOYLTQU-UHFFFAOYSA-M 4-aminobenzenesulfonate Chemical compound NC1=CC=C(S([O-])(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-M 0.000 description 1
• UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 description 1
• MDBVIOUGHSKRMT-UHFFFAOYSA-N 4-hydroxy-2-(trifluoromethyl)benzonitrile Chemical compound OC1=CC=C(C#N)C(C(F)(F)F)=C1 MDBVIOUGHSKRMT-UHFFFAOYSA-N 0.000 description 1
• NKOHRVBBQISBSB-UHFFFAOYSA-N 5-[(4-hydroxyphenyl)methyl]-1,3-thiazolidine-2,4-dione Chemical class C1=CC(O)=CC=C1CC1C(=O)NC(=O)S1 NKOHRVBBQISBSB-UHFFFAOYSA-N 0.000 description 1
• KBNDZENRCSHTJT-UHFFFAOYSA-N 5-[(9-methoxy-4-oxo-6,7-dihydropyrimido[6,1-a]isoquinolin-2-yl)oxy]-2-[3-(trifluoromethyl)phenoxy]benzonitrile Chemical compound C=1C(OC)=CC=C2C=1CCN(C(N=1)=O)C2=CC=1OC(C=C1C#N)=CC=C1OC1=CC=CC(C(F)(F)F)=C1 KBNDZENRCSHTJT-UHFFFAOYSA-N 0.000 description 1
• SEZJTSNMRZHIPB-UHFFFAOYSA-N 5-[2-fluoro-4-(hydroxymethyl)phenoxy]pyridine-3-carbonitrile Chemical compound FC1=CC(CO)=CC=C1OC1=CN=CC(C#N)=C1 SEZJTSNMRZHIPB-UHFFFAOYSA-N 0.000 description 1
• VFOBDHYPESAMAF-UHFFFAOYSA-N 6-(trifluoromethyl)pyridin-3-ol Chemical compound OC1=CC=C(C(F)(F)F)N=C1 VFOBDHYPESAMAF-UHFFFAOYSA-N 0.000 description 1
• UEJSQACTNVIJEC-UHFFFAOYSA-N 7-(2-cyclopentylethoxy)-1,2,2-trimethyl-3h-imidazo[1,2-c]pyrimidin-5-one Chemical compound N=1C(=O)N2CC(C)(C)N(C)C2=CC=1OCCC1CCCC1 UEJSQACTNVIJEC-UHFFFAOYSA-N 0.000 description 1
• MCOSJQQMXPNCKA-UHFFFAOYSA-N 7-[(2,4-difluorophenyl)methoxy]-1,2-dimethyl-2,3-dihydroimidazo[1,2-c]pyrimidin-5-one Chemical compound CN1C(C)CN(C(N=2)=O)C1=CC=2OCC1=CC=C(F)C=C1F MCOSJQQMXPNCKA-UHFFFAOYSA-N 0.000 description 1
• IBVIZIVOVLRMQP-UHFFFAOYSA-N 7-[(3,4-difluorophenyl)methoxy]-1,2-dimethyl-2,3-dihydroimidazo[1,2-c]pyrimidin-5-one Chemical compound CN1C(C)CN(C(N=2)=O)C1=CC=2OCC1=CC=C(F)C(F)=C1 IBVIZIVOVLRMQP-UHFFFAOYSA-N 0.000 description 1
• UYOVBYFJFSYTJM-UHFFFAOYSA-N 7-[(3,4-difluorophenyl)methoxy]-2,2-dimethyl-1,3-dihydroimidazo[1,2-c]pyrimidin-5-one Chemical compound N1C(C)(C)CN(C(N=2)=O)C1=CC=2OCC1=CC=C(F)C(F)=C1 UYOVBYFJFSYTJM-UHFFFAOYSA-N 0.000 description 1
• NJGQGETWLURBCF-UHFFFAOYSA-N 7-[(3,5-difluorophenyl)methoxy]-1,2-dimethyl-2,3-dihydroimidazo[1,2-c]pyrimidin-5-one Chemical compound CN1C(C)CN(C(N=2)=O)C1=CC=2OCC1=CC(F)=CC(F)=C1 NJGQGETWLURBCF-UHFFFAOYSA-N 0.000 description 1
• HKGFUPKUQGGYRP-UHFFFAOYSA-N 7-[(3-chloro-4-fluorophenyl)methoxy]-1,2-dimethyl-2,3-dihydroimidazo[1,2-c]pyrimidin-5-one Chemical compound CN1C(C)CN(C(N=2)=O)C1=CC=2OCC1=CC=C(F)C(Cl)=C1 HKGFUPKUQGGYRP-UHFFFAOYSA-N 0.000 description 1
• UJYHTAWIAUXISG-UHFFFAOYSA-N 7-[(3-chlorophenyl)methoxy]-1,2,2-trimethyl-3h-imidazo[1,2-c]pyrimidin-5-one Chemical compound N=1C(=O)N2CC(C)(C)N(C)C2=CC=1OCC1=CC=CC(Cl)=C1 UJYHTAWIAUXISG-UHFFFAOYSA-N 0.000 description 1
• APWPYPNKNNVPRJ-UHFFFAOYSA-N 7-[2-(2,3-difluorophenyl)ethoxy]-1,2,2-trimethyl-3h-imidazo[1,2-c]pyrimidin-5-one Chemical compound N=1C(=O)N2CC(C)(C)N(C)C2=CC=1OCCC1=CC=CC(F)=C1F APWPYPNKNNVPRJ-UHFFFAOYSA-N 0.000 description 1
• DYJLMNQFDRNDPC-UHFFFAOYSA-N 7-[2-(3,4-difluorophenyl)ethoxy]-1,2,2-trimethyl-3h-imidazo[1,2-c]pyrimidin-5-one Chemical compound N=1C(=O)N2CC(C)(C)N(C)C2=CC=1OCCC1=CC=C(F)C(F)=C1 DYJLMNQFDRNDPC-UHFFFAOYSA-N 0.000 description 1
• UCUCGOYGASXPRN-UHFFFAOYSA-N 7-[2-(3,5-difluorophenyl)ethoxy]-1,2,2-trimethyl-3h-imidazo[1,2-c]pyrimidin-5-one Chemical compound N=1C(=O)N2CC(C)(C)N(C)C2=CC=1OCCC1=CC(F)=CC(F)=C1 UCUCGOYGASXPRN-UHFFFAOYSA-N 0.000 description 1
• YFIDBOAOVFQGOA-UHFFFAOYSA-N 7-[[3,5-difluoro-4-[2-(trifluoromethyl)pyridin-4-yl]oxyphenyl]methoxy]-1,2,2-trimethyl-3h-imidazo[1,2-c]pyrimidin-5-one Chemical compound N=1C(=O)N2CC(C)(C)N(C)C2=CC=1OCC(C=C1F)=CC(F)=C1OC1=CC=NC(C(F)(F)F)=C1 YFIDBOAOVFQGOA-UHFFFAOYSA-N 0.000 description 1
• YHOFKKLLDFRJNZ-UHFFFAOYSA-N 7-[[3,5-difluoro-4-[2-(trifluoromethyl)pyridin-4-yl]oxyphenyl]methoxy]-2,2-dimethyl-1,3-dihydroimidazo[1,2-c]pyrimidin-5-one Chemical compound N1C(C)(C)CN(C(N=2)=O)C1=CC=2OCC(C=C1F)=CC(F)=C1OC1=CC=NC(C(F)(F)F)=C1 YHOFKKLLDFRJNZ-UHFFFAOYSA-N 0.000 description 1
• IFHGBPZIQDGBMW-UHFFFAOYSA-N 7-[[3,5-difluoro-4-[2-(trifluoromethyl)pyrimidin-5-yl]oxyphenyl]methoxy]-2,2-dimethyl-1,3-dihydroimidazo[1,2-c]pyrimidin-5-one Chemical compound N1C(C)(C)CN(C(N=2)=O)C1=CC=2OCC(C=C1F)=CC(F)=C1OC1=CN=C(C(F)(F)F)N=C1 IFHGBPZIQDGBMW-UHFFFAOYSA-N 0.000 description 1
• GHKFBKAAAKHBKQ-UHFFFAOYSA-N 7-[[3,5-difluoro-4-[5-(trifluoromethyl)pyridin-3-yl]oxyphenyl]methoxy]-1,2,2-trimethyl-3h-imidazo[1,2-c]pyrimidin-5-one Chemical compound N=1C(=O)N2CC(C)(C)N(C)C2=CC=1OCC(C=C1F)=CC(F)=C1OC1=CN=CC(C(F)(F)F)=C1 GHKFBKAAAKHBKQ-UHFFFAOYSA-N 0.000 description 1
• ZZSAGWPRLPRFJC-UHFFFAOYSA-N 7-[[3,5-difluoro-4-[5-(trifluoromethyl)pyridin-3-yl]oxyphenyl]methoxy]-2,2-dimethyl-1,3-dihydroimidazo[1,2-c]pyrimidin-5-one Chemical compound N1C(C)(C)CN(C(N=2)=O)C1=CC=2OCC(C=C1F)=CC(F)=C1OC1=CN=CC(C(F)(F)F)=C1 ZZSAGWPRLPRFJC-UHFFFAOYSA-N 0.000 description 1
• RCSQXMVMKSJNIB-UHFFFAOYSA-N 7-[[3,5-difluoro-4-[6-(trifluoromethyl)pyridin-3-yl]oxyphenyl]methoxy]-1,2,2-trimethyl-3h-imidazo[1,2-c]pyrimidin-5-one Chemical compound N=1C(=O)N2CC(C)(C)N(C)C2=CC=1OCC(C=C1F)=CC(F)=C1OC1=CC=C(C(F)(F)F)N=C1 RCSQXMVMKSJNIB-UHFFFAOYSA-N 0.000 description 1
• GVRMCFWGHNGXKJ-UHFFFAOYSA-N 7-[[3,5-difluoro-4-[6-(trifluoromethyl)pyridin-3-yl]oxyphenyl]methoxy]-2,2-dimethyl-1,3-dihydroimidazo[1,2-c]pyrimidin-5-one Chemical compound N1C(C)(C)CN(C(N=2)=O)C1=CC=2OCC(C=C1F)=CC(F)=C1OC1=CC=C(C(F)(F)F)N=C1 GVRMCFWGHNGXKJ-UHFFFAOYSA-N 0.000 description 1
• PTWJLCSPVLUCPP-UHFFFAOYSA-N 7-[[3-fluoro-4-(2-fluoropyridin-4-yl)oxyphenyl]methoxy]-2,2-dimethyl-1,3-dihydroimidazo[1,2-c]pyrimidin-5-one Chemical compound N1C(C)(C)CN(C(N=2)=O)C1=CC=2OCC(C=C1F)=CC=C1OC1=CC=NC(F)=C1 PTWJLCSPVLUCPP-UHFFFAOYSA-N 0.000 description 1
• WMLXXSNVZQBSBW-UHFFFAOYSA-N 7-[[3-fluoro-4-(6-fluoropyridin-3-yl)oxyphenyl]methoxy]-2,2-dimethyl-1,3-dihydroimidazo[1,2-c]pyrimidin-5-one Chemical compound N1C(C)(C)CN(C(N=2)=O)C1=CC=2OCC(C=C1F)=CC=C1OC1=CC=C(F)N=C1 WMLXXSNVZQBSBW-UHFFFAOYSA-N 0.000 description 1
• LQXOHPHXZXLQBS-UHFFFAOYSA-N 7-[[3-fluoro-4-[2-(trifluoromethyl)pyridin-4-yl]oxyphenyl]methoxy]-1,2,2-trimethyl-3h-imidazo[1,2-c]pyrimidin-5-one Chemical compound N=1C(=O)N2CC(C)(C)N(C)C2=CC=1OCC(C=C1F)=CC=C1OC1=CC=NC(C(F)(F)F)=C1 LQXOHPHXZXLQBS-UHFFFAOYSA-N 0.000 description 1
• WDMVJIVUHJLAHR-UHFFFAOYSA-N 7-[[3-fluoro-4-[2-(trifluoromethyl)pyrimidin-5-yl]oxyphenyl]methoxy]-1,2,2-trimethyl-3h-imidazo[1,2-c]pyrimidin-5-one Chemical compound N=1C(=O)N2CC(C)(C)N(C)C2=CC=1OCC(C=C1F)=CC=C1OC1=CN=C(C(F)(F)F)N=C1 WDMVJIVUHJLAHR-UHFFFAOYSA-N 0.000 description 1
• ZPDFIDGXTLWWRE-UHFFFAOYSA-N 7-[[3-fluoro-4-[3-fluoro-5-(trifluoromethyl)phenoxy]phenyl]methoxy]-2,3-dihydro-1h-imidazo[1,2-c]pyrimidin-5-one Chemical compound FC(F)(F)C1=CC(F)=CC(OC=2C(=CC(COC3=NC(=O)N4CCNC4=C3)=CC=2)F)=C1 ZPDFIDGXTLWWRE-UHFFFAOYSA-N 0.000 description 1
• PPKNPJKYLRQSCE-UHFFFAOYSA-N 7-[[3-fluoro-4-[5-(trifluoromethyl)pyridin-3-yl]oxyphenyl]methoxy]-1,2,2-trimethyl-3h-imidazo[1,2-c]pyrimidin-5-one Chemical compound N=1C(=O)N2CC(C)(C)N(C)C2=CC=1OCC(C=C1F)=CC=C1OC1=CN=CC(C(F)(F)F)=C1 PPKNPJKYLRQSCE-UHFFFAOYSA-N 0.000 description 1
• BREORLPTFXWGED-UHFFFAOYSA-N 7-[[3-fluoro-4-[6-(trifluoromethyl)pyridin-3-yl]oxyphenyl]methoxy]-1,2,2-trimethyl-3h-imidazo[1,2-c]pyrimidin-5-one Chemical compound N=1C(=O)N2CC(C)(C)N(C)C2=CC=1OCC(C=C1F)=CC=C1OC1=CC=C(C(F)(F)F)N=C1 BREORLPTFXWGED-UHFFFAOYSA-N 0.000 description 1
• TYHGLQGOJOAMOD-UHFFFAOYSA-N 7-[[4-[4-chloro-3-(trifluoromethyl)phenoxy]phenyl]methoxy]-1-cyclopropyl-2,3-dihydroimidazo[1,2-c]pyrimidin-5-one Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(OC=2C=CC(COC3=NC(=O)N4CCN(C4=C3)C3CC3)=CC=2)=C1 TYHGLQGOJOAMOD-UHFFFAOYSA-N 0.000 description 1
• JKGLHQUHQJJEDR-UHFFFAOYSA-N 7-chloro-1-ethyl-2,2-dimethyl-3h-imidazo[1,2-c]pyrimidin-5-one Chemical compound ClC1=NC(=O)N2CC(C)(C)N(CC)C2=C1 JKGLHQUHQJJEDR-UHFFFAOYSA-N 0.000 description 1
• FNYNEWUOZJSFSG-UHFFFAOYSA-N 7-chloro-2,2-dimethyl-1-propan-2-yl-3h-imidazo[1,2-c]pyrimidin-5-one Chemical compound ClC1=NC(=O)N2CC(C)(C)N(C(C)C)C2=C1 FNYNEWUOZJSFSG-UHFFFAOYSA-N 0.000 description 1
• 244000215068 Acacia senegal Species 0.000 description 1
• NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
• OGSPWJRAVKPPFI-UHFFFAOYSA-N Alendronic Acid Chemical compound NCCCC(O)(P(O)(O)=O)P(O)(O)=O OGSPWJRAVKPPFI-UHFFFAOYSA-N 0.000 description 1
• 239000004229 Alkannin Substances 0.000 description 1
• GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
• 206010002556 Ankylosing Spondylitis Diseases 0.000 description 1
• 206010003211 Arteriosclerosis coronary artery Diseases 0.000 description 1
• 206010003267 Arthritis reactive Diseases 0.000 description 1
• 241000416162 Astragalus gummifer Species 0.000 description 1
• XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 description 1
• XUKUURHRXDUEBC-UHFFFAOYSA-N Atorvastatin Natural products C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CCC(O)CC(O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-UHFFFAOYSA-N 0.000 description 1
• 208000032116 Autoimmune Experimental Encephalomyelitis Diseases 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
• 208000020084 Bone disease Diseases 0.000 description 1
• 206010065687 Bone loss Diseases 0.000 description 1
• 241000283690 Bos taurus Species 0.000 description 1
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
• FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
• 102000055006 Calcitonin Human genes 0.000 description 1
• 108060001064 Calcitonin Proteins 0.000 description 1
• 241000283707 Capra Species 0.000 description 1
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
• 241000282693 Cercopithecidae Species 0.000 description 1
• 208000005145 Cerebral amyloid angiopathy Diseases 0.000 description 1
• 206010008111 Cerebral haemorrhage Diseases 0.000 description 1
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
• 229940127328 Cholesterol Synthesis Inhibitors Drugs 0.000 description 1
• 206010060774 Chondrosis Diseases 0.000 description 1
• 208000016623 Choroid neoplasm Diseases 0.000 description 1
• 229920002785 Croscarmellose sodium Polymers 0.000 description 1
• 102100025621 Cytochrome b-245 heavy chain Human genes 0.000 description 1
• FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
• FBPFZTCFMRRESA-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
• QNAYBMKLOCPYGJ-UWTATZPHSA-N D-alanine Chemical compound C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 description 1
• FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
• 239000001692 EU approved anti-caking agent Substances 0.000 description 1
• 241000283073 Equus caballus Species 0.000 description 1
• PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
• KBLAIGYISWOQHJ-NSHDSACASA-N FC1=C(C#N)C=C(C=C1)C([C@@H](N)CCSC)=O Chemical compound FC1=C(C#N)C=C(C=C1)C([C@@H](N)CCSC)=O KBLAIGYISWOQHJ-NSHDSACASA-N 0.000 description 1
• 239000001263 FEMA 3042 Substances 0.000 description 1
• 239000004230 Fast Yellow AB Substances 0.000 description 1
• 241000282326 Felis catus Species 0.000 description 1
• BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
• 108010010803 Gelatin Proteins 0.000 description 1
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
• AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 1
• AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical class OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 1
• 229920000084 Gum arabic Polymers 0.000 description 1
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
• 208000035150 Hypercholesterolemia Diseases 0.000 description 1
• 206010020850 Hyperthyroidism Diseases 0.000 description 1
• 206010062016 Immunosuppression Diseases 0.000 description 1
• 239000004233 Indanthrene blue RS Substances 0.000 description 1
• 208000022559 Inflammatory bowel disease Diseases 0.000 description 1
• 208000003456 Juvenile Arthritis Diseases 0.000 description 1
• 206010059176 Juvenile idiopathic arthritis Diseases 0.000 description 1
• 208000011200 Kawasaki disease Diseases 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
• JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 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
• JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
• 108010033266 Lipoprotein(a) Proteins 0.000 description 1
• 102000057248 Lipoprotein(a) Human genes 0.000 description 1
• 208000016604 Lyme disease Diseases 0.000 description 1
• 206010025421 Macule Diseases 0.000 description 1
• 241000124008 Mammalia Species 0.000 description 1
• 229930195725 Mannitol Natural products 0.000 description 1
• 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
• LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
• 238000006845 Michael addition reaction Methods 0.000 description 1
• 208000005314 Multi-Infarct Dementia Diseases 0.000 description 1
• 102000047918 Myelin Basic Human genes 0.000 description 1
• 101710107068 Myelin basic protein Proteins 0.000 description 1
• 229930193140 Neomycin Natural products 0.000 description 1
• 208000012902 Nervous system disease Diseases 0.000 description 1
• 208000022873 Ocular disease Diseases 0.000 description 1
• 206010030113 Oedema Diseases 0.000 description 1
• 239000004235 Orange GGN Substances 0.000 description 1
• 208000010191 Osteitis Deformans Diseases 0.000 description 1
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
• 102000000536 PPAR gamma Human genes 0.000 description 1
• 108010016731 PPAR gamma Proteins 0.000 description 1
• 208000027868 Paget disease Diseases 0.000 description 1
• 241001494479 Pecora Species 0.000 description 1
• LRBQNJMCXXYXIU-PPKXGCFTSA-N Penta-digallate-beta-D-glucose Natural products OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-PPKXGCFTSA-N 0.000 description 1
• 241000009328 Perro Species 0.000 description 1
• 244000046052 Phaseolus vulgaris Species 0.000 description 1
• 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
• 108010003541 Platelet Activating Factor Proteins 0.000 description 1
• 239000004237 Ponceau 6R Substances 0.000 description 1
• 239000004236 Ponceau SX Substances 0.000 description 1
• TUZYXOIXSAXUGO-UHFFFAOYSA-N Pravastatin Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(O)C=C21 TUZYXOIXSAXUGO-UHFFFAOYSA-N 0.000 description 1
• 206010036790 Productive cough Diseases 0.000 description 1
• 206010037660 Pyrexia Diseases 0.000 description 1
• LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 description 1
• 208000001647 Renal Insufficiency Diseases 0.000 description 1
• 206010038848 Retinal detachment Diseases 0.000 description 1
• 206010038910 Retinitis Diseases 0.000 description 1
• 239000004231 Riboflavin-5-Sodium Phosphate Substances 0.000 description 1
• IIDJRNMFWXDHID-UHFFFAOYSA-N Risedronic acid Chemical compound OP(=O)(O)C(P(O)(O)=O)(O)CC1=CC=CN=C1 IIDJRNMFWXDHID-UHFFFAOYSA-N 0.000 description 1
• RYMZZMVNJRMUDD-UHFFFAOYSA-N SJ000286063 Natural products C12C(OC(=O)C(C)(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 RYMZZMVNJRMUDD-UHFFFAOYSA-N 0.000 description 1
• 206010039491 Sarcoma Diseases 0.000 description 1
• MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
• 235000021355 Stearic acid Nutrition 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
• 241000282887 Suidae Species 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
• STSCVKRWJPWALQ-UHFFFAOYSA-N TRIFLUOROACETIC ACID ETHYL ESTER Chemical compound CCOC(=O)C(F)(F)F STSCVKRWJPWALQ-UHFFFAOYSA-N 0.000 description 1
• 206010043189 Telangiectasia Diseases 0.000 description 1
• 108010049264 Teriparatide Proteins 0.000 description 1
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
• 229920001615 Tragacanth Polymers 0.000 description 1
• 108060008682 Tumor Necrosis Factor Proteins 0.000 description 1
• 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 1
• 206010046851 Uveitis Diseases 0.000 description 1
• 208000001445 Uveomeningoencephalitic Syndrome Diseases 0.000 description 1
• 206010063661 Vascular encephalopathy Diseases 0.000 description 1
• 208000034705 Vogt-Koyanagi-Harada syndrome Diseases 0.000 description 1
• 239000004234 Yellow 2G Substances 0.000 description 1
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
• GDBLBSZHLUVKQP-UHFFFAOYSA-N [3,5-difluoro-4-(2-fluoropyridin-4-yl)oxyphenyl]methanol Chemical compound FC1=CC(CO)=CC(F)=C1OC1=CC=NC(F)=C1 GDBLBSZHLUVKQP-UHFFFAOYSA-N 0.000 description 1
• ROFLASBZYJIMRC-UHFFFAOYSA-N [3,5-difluoro-4-(3-fluorophenoxy)phenyl]methanol Chemical compound FC1=CC(CO)=CC(F)=C1OC1=CC=CC(F)=C1 ROFLASBZYJIMRC-UHFFFAOYSA-N 0.000 description 1
• MSHRRHUOKCGTKL-UHFFFAOYSA-N [4-(3,4-difluorophenoxy)-3,5-difluorophenyl]methanol Chemical compound FC1=CC(CO)=CC(F)=C1OC1=CC=C(F)C(F)=C1 MSHRRHUOKCGTKL-UHFFFAOYSA-N 0.000 description 1
• UOGCMIDHVWTYEZ-UHFFFAOYSA-N [4-[4-chloro-3-(trifluoromethyl)phenoxy]phenyl]methanol Chemical compound C1=CC(CO)=CC=C1OC1=CC=C(Cl)C(C(F)(F)F)=C1 UOGCMIDHVWTYEZ-UHFFFAOYSA-N 0.000 description 1
• DGBDVJVPBJMVDH-UHFFFAOYSA-N [4-fluoro-3-(trifluoromethyl)phenyl]methanol Chemical compound OCC1=CC=C(F)C(C(F)(F)F)=C1 DGBDVJVPBJMVDH-UHFFFAOYSA-N 0.000 description 1
• JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
• 235000010489 acacia gum Nutrition 0.000 description 1
• 239000000205 acacia gum Substances 0.000 description 1
• 238000009825 accumulation Methods 0.000 description 1
• 150000001242 acetic acid derivatives Chemical class 0.000 description 1
• DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
• 150000007513 acids Chemical class 0.000 description 1
• 229940048053 acrylate Drugs 0.000 description 1
• 239000012190 activator Substances 0.000 description 1
• 230000001154 acute effect Effects 0.000 description 1
• 238000009098 adjuvant therapy Methods 0.000 description 1
• 239000000443 aerosol Substances 0.000 description 1
• 229940062527 alendronate Drugs 0.000 description 1
• 235000019232 alkannin Nutrition 0.000 description 1
• 239000002168 alkylating agent Substances 0.000 description 1
• 229940100198 alkylating agent Drugs 0.000 description 1
• 239000004191 allura red AC Substances 0.000 description 1
• 235000012741 allura red AC Nutrition 0.000 description 1
• 239000004178 amaranth Substances 0.000 description 1
• 235000012735 amaranth Nutrition 0.000 description 1
• 150000001412 amines Chemical class 0.000 description 1
• 150000001413 amino acids Chemical class 0.000 description 1
• CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 1
• 229910021529 ammonia Inorganic materials 0.000 description 1
• 239000005557 antagonist Substances 0.000 description 1
• 210000002551 anterior cerebral artery Anatomy 0.000 description 1
• 230000000879 anti-atherosclerotic effect Effects 0.000 description 1
• 229940121363 anti-inflammatory agent Drugs 0.000 description 1
• 239000002260 anti-inflammatory agent Substances 0.000 description 1
• 229940124599 anti-inflammatory drug Drugs 0.000 description 1
• 239000003529 anticholesteremic agent Substances 0.000 description 1
• 229940127226 anticholesterol agent Drugs 0.000 description 1
• 239000003472 antidiabetic agent Substances 0.000 description 1
• 229940125708 antidiabetic agent Drugs 0.000 description 1
• 239000000427 antigen Substances 0.000 description 1
• 102000036639 antigens Human genes 0.000 description 1
• 108091007433 antigens Proteins 0.000 description 1
• 229940030600 antihypertensive agent Drugs 0.000 description 1
• 239000002220 antihypertensive agent Substances 0.000 description 1
• 230000006907 apoptotic process Effects 0.000 description 1
• 239000003125 aqueous solvent Substances 0.000 description 1
• 150000004982 aromatic amines Chemical class 0.000 description 1
• 206010003246 arthritis Diseases 0.000 description 1
• 229940072107 ascorbate Drugs 0.000 description 1
• 235000010323 ascorbic acid Nutrition 0.000 description 1
• 239000011668 ascorbic acid Substances 0.000 description 1
• 238000011914 asymmetric synthesis Methods 0.000 description 1
• 229960005370 atorvastatin Drugs 0.000 description 1
• 239000004176 azorubin Substances 0.000 description 1
• 235000012733 azorubine Nutrition 0.000 description 1
• 230000004888 barrier function Effects 0.000 description 1
• 210000002469 basement membrane Anatomy 0.000 description 1
• 230000009286 beneficial effect Effects 0.000 description 1
• 230000008901 benefit Effects 0.000 description 1
• 229940077388 benzenesulfonate Drugs 0.000 description 1
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
• 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
• FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 1
• WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
• 230000027455 binding Effects 0.000 description 1
• 238000011953 bioanalysis Methods 0.000 description 1
• 238000012742 biochemical analysis Methods 0.000 description 1
• 230000033228 biological regulation Effects 0.000 description 1
• KNWTWMCERYGTLD-UHFFFAOYSA-N bis(3,4-difluorophenyl)methanol Chemical compound C=1C=C(F)C(F)=CC=1C(O)C1=CC=C(F)C(F)=C1 KNWTWMCERYGTLD-UHFFFAOYSA-N 0.000 description 1
• 230000000903 blocking effect Effects 0.000 description 1
• 230000037118 bone strength Effects 0.000 description 1
• 208000025698 brain inflammatory disease Diseases 0.000 description 1
• 239000004161 brilliant blue FCF Substances 0.000 description 1
• 235000012745 brilliant blue FCF Nutrition 0.000 description 1
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
• 229910052794 bromium Inorganic materials 0.000 description 1
• 239000006189 buccal tablet Substances 0.000 description 1
• 239000000872 buffer Substances 0.000 description 1
• 239000007853 buffer solution 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
• 229910052792 caesium Inorganic materials 0.000 description 1
• BBBFJLBPOGFECG-VJVYQDLKSA-N calcitonin Chemical compound N([C@H](C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(N)=O)C(C)C)C(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1 BBBFJLBPOGFECG-VJVYQDLKSA-N 0.000 description 1
• 229960004015 calcitonin Drugs 0.000 description 1
• 229960005069 calcium Drugs 0.000 description 1
• FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 1
• CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
• 239000008116 calcium stearate Substances 0.000 description 1
• 235000013539 calcium stearate Nutrition 0.000 description 1
• 239000007894 caplet Substances 0.000 description 1
• 239000001768 carboxy methyl cellulose Substances 0.000 description 1
• 230000007211 cardiovascular event Effects 0.000 description 1
• 239000004106 carminic acid Substances 0.000 description 1
• 235000012730 carminic acid Nutrition 0.000 description 1
• 210000000845 cartilage Anatomy 0.000 description 1
• 230000003197 catalytic effect Effects 0.000 description 1
• 150000001768 cations Chemical class 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
• 210000003169 central nervous system Anatomy 0.000 description 1
• 208000015114 central nervous system disease Diseases 0.000 description 1
• 201000005667 central retinal vein occlusion Diseases 0.000 description 1
• 230000002490 cerebral effect Effects 0.000 description 1
• 229960005110 cerivastatin Drugs 0.000 description 1
• SEERZIQQUAZTOL-ANMDKAQQSA-N cerivastatin Chemical compound COCC1=C(C(C)C)N=C(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC(O)=O)=C1C1=CC=C(F)C=C1 SEERZIQQUAZTOL-ANMDKAQQSA-N 0.000 description 1
• 230000008859 change Effects 0.000 description 1
• 239000002738 chelating agent Substances 0.000 description 1
• 125000004803 chlorobenzyl group Chemical group 0.000 description 1
• 208000019069 chronic childhood arthritis Diseases 0.000 description 1
• 208000016532 chronic granulomatous disease Diseases 0.000 description 1
• 229940001468 citrate Drugs 0.000 description 1
• 239000001679 citrus red 2 Substances 0.000 description 1
• 235000013986 citrus red 2 Nutrition 0.000 description 1
• 239000011248 coating agent Substances 0.000 description 1
• 235000020057 cognac Nutrition 0.000 description 1
• 208000010877 cognitive disease Diseases 0.000 description 1
• 239000012230 colorless oil Substances 0.000 description 1
• 238000004440 column chromatography Methods 0.000 description 1
• 229940125782 compound 2 Drugs 0.000 description 1
• 229940126214 compound 3 Drugs 0.000 description 1
• RFKZUAOAYVHBOY-UHFFFAOYSA-M copper(1+);acetate Chemical compound [Cu+].CC([O-])=O RFKZUAOAYVHBOY-UHFFFAOYSA-M 0.000 description 1
• 208000026758 coronary atherosclerosis Diseases 0.000 description 1
• 239000006184 cosolvent Substances 0.000 description 1
• 235000001671 coumarin Nutrition 0.000 description 1
• 229960000956 coumarin Drugs 0.000 description 1
• 238000005336 cracking Methods 0.000 description 1
• 239000006071 cream Substances 0.000 description 1
• 229960000913 crospovidone Drugs 0.000 description 1
• 238000002425 crystallisation Methods 0.000 description 1
• 230000008025 crystallization Effects 0.000 description 1
• 239000004148 curcumin Substances 0.000 description 1
• WLVKDFJTYKELLQ-UHFFFAOYSA-N cyclopropylboronic acid Chemical compound OB(O)C1CC1 WLVKDFJTYKELLQ-UHFFFAOYSA-N 0.000 description 1
• DEZRYPDIMOWBDS-UHFFFAOYSA-N dcm dichloromethane Chemical compound ClCCl.ClCCl DEZRYPDIMOWBDS-UHFFFAOYSA-N 0.000 description 1
• 230000034994 death Effects 0.000 description 1
• 210000004443 dendritic cell Anatomy 0.000 description 1
• 239000007933 dermal patch Substances 0.000 description 1
• 230000006866 deterioration Effects 0.000 description 1
• 150000001975 deuterium Chemical group 0.000 description 1
• 229910052805 deuterium Inorganic materials 0.000 description 1
• 239000008121 dextrose Substances 0.000 description 1
• 150000004985 diamines Chemical class 0.000 description 1
• 235000019700 dicalcium phosphate Nutrition 0.000 description 1
• 125000003963 dichloro group Chemical group Cl* 0.000 description 1
• ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
• IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
• UXGNZZKBCMGWAZ-UHFFFAOYSA-N dimethylformamide dmf Chemical compound CN(C)C=O.CN(C)C=O UXGNZZKBCMGWAZ-UHFFFAOYSA-N 0.000 description 1
• XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 1
• 208000035475 disorder Diseases 0.000 description 1
• 238000004821 distillation Methods 0.000 description 1
• 238000009826 distribution Methods 0.000 description 1
• 229930004069 diterpene Natural products 0.000 description 1
• POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
• 230000002222 downregulating effect Effects 0.000 description 1
• 230000009977 dual effect Effects 0.000 description 1
• 239000003995 emulsifying agent Substances 0.000 description 1
• 206010014599 encephalitis Diseases 0.000 description 1
• 239000004174 erythrosine Substances 0.000 description 1
• 235000012732 erythrosine Nutrition 0.000 description 1
• AFAXGSQYZLGZPG-UHFFFAOYSA-L ethane-1,2-disulfonate Chemical compound [O-]S(=O)(=O)CCS([O-])(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-L 0.000 description 1
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
• PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 1
• 229940108366 exelon Drugs 0.000 description 1
• 208000012997 experimental autoimmune encephalomyelitis Diseases 0.000 description 1
• 239000000284 extract Substances 0.000 description 1
• 201000005577 familial hyperlipidemia Diseases 0.000 description 1
• 235000019233 fast yellow AB Nutrition 0.000 description 1
• 239000000835 fiber Substances 0.000 description 1
• 239000012065 filter cake Substances 0.000 description 1
• 239000012847 fine chemical Substances 0.000 description 1
• 235000019634 flavors Nutrition 0.000 description 1
• 125000001153 fluoro group Chemical group F* 0.000 description 1
• 229960003765 fluvastatin Drugs 0.000 description 1
• 235000013355 food flavoring agent Nutrition 0.000 description 1
• 235000003599 food sweetener Nutrition 0.000 description 1
• 229940044170 formate Drugs 0.000 description 1
• 235000019253 formic acid Nutrition 0.000 description 1
• 229940050411 fumarate Drugs 0.000 description 1
• 125000000524 functional group Chemical group 0.000 description 1
• 229960003980 galantamine Drugs 0.000 description 1
• ASUTZQLVASHGKV-UHFFFAOYSA-N galanthamine hydrochloride Natural products O1C(=C23)C(OC)=CC=C2CN(C)CCC23C1CC(O)C=C2 ASUTZQLVASHGKV-UHFFFAOYSA-N 0.000 description 1
• 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
• 239000000499 gel Substances 0.000 description 1
• 239000008273 gelatin Substances 0.000 description 1
• 229920000159 gelatin Polymers 0.000 description 1
• 235000019322 gelatine Nutrition 0.000 description 1
• 235000011852 gelatine desserts Nutrition 0.000 description 1
• 238000007429 general method Methods 0.000 description 1
• 229930195712 glutamate Natural products 0.000 description 1
• JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
• 239000008187 granular material Substances 0.000 description 1
• 239000003979 granulating agent Substances 0.000 description 1
• 210000004326 gyrus cinguli Anatomy 0.000 description 1
• 125000001188 haloalkyl group Chemical group 0.000 description 1
• 229910052736 halogen Inorganic materials 0.000 description 1
• 150000002367 halogens Chemical class 0.000 description 1
• 230000002008 hemorrhagic effect Effects 0.000 description 1
• MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
• IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
• 229940088597 hormone Drugs 0.000 description 1
• 239000005556 hormone Substances 0.000 description 1
• 239000003906 humectant Substances 0.000 description 1
• 230000036571 hydration Effects 0.000 description 1
• 238000006703 hydration reaction Methods 0.000 description 1
• 150000002430 hydrocarbons Chemical group 0.000 description 1
• 150000003840 hydrochlorides Chemical class 0.000 description 1
• 230000003301 hydrolyzing effect Effects 0.000 description 1
• 208000013403 hyperactivity Diseases 0.000 description 1
• 230000000260 hypercholesteremic effect Effects 0.000 description 1
• 210000003016 hypothalamus Anatomy 0.000 description 1
• 239000005457 ice water Substances 0.000 description 1
• 230000003053 immunization Effects 0.000 description 1
• 230000001506 immunosuppresive effect Effects 0.000 description 1
• 238000000338 in vitro Methods 0.000 description 1
• 238000001727 in vivo Methods 0.000 description 1
• 238000010348 incorporation Methods 0.000 description 1
• 235000019239 indanthrene blue RS Nutrition 0.000 description 1
• 239000004179 indigotine Substances 0.000 description 1
• 235000012738 indigotine Nutrition 0.000 description 1
• 230000007574 infarction Effects 0.000 description 1
• 230000028709 inflammatory response Effects 0.000 description 1
• 230000002452 interceptive effect Effects 0.000 description 1
• 238000007918 intramuscular administration Methods 0.000 description 1
• 238000001990 intravenous administration Methods 0.000 description 1
• 229910052740 iodine Inorganic materials 0.000 description 1
• 239000011630 iodine Substances 0.000 description 1
• SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
• KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
• 238000006317 isomerization reaction Methods 0.000 description 1
• 230000000155 isotopic effect Effects 0.000 description 1
• 201000002215 juvenile rheumatoid arthritis Diseases 0.000 description 1
• 201000006370 kidney failure Diseases 0.000 description 1
• 229940116871 l-lactate Drugs 0.000 description 1
• 239000008101 lactose Substances 0.000 description 1
• 229940070765 laurate Drugs 0.000 description 1
• 210000000265 leukocyte Anatomy 0.000 description 1
• WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Inorganic materials [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 1
• 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 1
• GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 1
• 238000011068 loading method Methods 0.000 description 1
• 230000008752 local inflammatory process Effects 0.000 description 1
• 239000006210 lotion Substances 0.000 description 1
• 206010025135 lupus erythematosus Diseases 0.000 description 1
• 235000019359 magnesium stearate Nutrition 0.000 description 1
• 229940049920 malate Drugs 0.000 description 1
• BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
• 208000027202 mammary Paget disease Diseases 0.000 description 1
• IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
• 239000000594 mannitol Substances 0.000 description 1
• 235000010355 mannitol Nutrition 0.000 description 1
• 230000000873 masking effect Effects 0.000 description 1
• 239000012528 membrane Substances 0.000 description 1
• 210000004379 membrane Anatomy 0.000 description 1
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
• 229960000485 methotrexate Drugs 0.000 description 1
• IZYBEMGNIUSSAX-UHFFFAOYSA-N methyl benzenecarboperoxoate Chemical compound COOC(=O)C1=CC=CC=C1 IZYBEMGNIUSSAX-UHFFFAOYSA-N 0.000 description 1
• 229940095102 methyl benzoate Drugs 0.000 description 1
• LRMHVVPPGGOAJQ-UHFFFAOYSA-N methyl nitrate Chemical class CO[N+]([O-])=O LRMHVVPPGGOAJQ-UHFFFAOYSA-N 0.000 description 1
• 208000027061 mild cognitive impairment Diseases 0.000 description 1
• 150000007522 mineralic acids Chemical class 0.000 description 1
• 238000012986 modification Methods 0.000 description 1
• 230000004048 modification Effects 0.000 description 1
• 239000003068 molecular probe Substances 0.000 description 1
• 208000001725 mucocutaneous lymph node syndrome Diseases 0.000 description 1
• PEECTLLHENGOKU-UHFFFAOYSA-N n,n-dimethylpyridin-4-amine Chemical compound CN(C)C1=CC=NC=C1.CN(C)C1=CC=NC=C1 PEECTLLHENGOKU-UHFFFAOYSA-N 0.000 description 1
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 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
• 230000001338 necrotic effect Effects 0.000 description 1
• 229960004927 neomycin Drugs 0.000 description 1
• 238000002610 neuroimaging Methods 0.000 description 1
• 230000000926 neurological effect Effects 0.000 description 1
• 230000007658 neurological function Effects 0.000 description 1
• 150000002823 nitrates Chemical class 0.000 description 1
• OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
• 239000002674 ointment Substances 0.000 description 1
• 229940049964 oleate Drugs 0.000 description 1
• ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
• 239000006186 oral dosage form Substances 0.000 description 1
• 235000019236 orange GGN Nutrition 0.000 description 1
• 150000007524 organic acids Chemical class 0.000 description 1
• 235000005985 organic acids Nutrition 0.000 description 1
• 230000003204 osmotic effect Effects 0.000 description 1
• 230000036542 oxidative stress Effects 0.000 description 1
• IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
• QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
• 230000000849 parathyroid Effects 0.000 description 1
• 210000001152 parietal lobe Anatomy 0.000 description 1
• 239000006072 paste Substances 0.000 description 1
• 239000004177 patent blue V Substances 0.000 description 1
• 235000012736 patent blue V Nutrition 0.000 description 1
• 230000008506 pathogenesis Effects 0.000 description 1
• 230000035699 permeability Effects 0.000 description 1
• 235000020030 perry Nutrition 0.000 description 1
• 210000001539 phagocyte Anatomy 0.000 description 1
• 229940124531 pharmaceutical excipient Drugs 0.000 description 1
• WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
• 239000010452 phosphate Substances 0.000 description 1
• 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
• XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
• 238000013310 pig model Methods 0.000 description 1
• 230000019612 pigmentation Effects 0.000 description 1
• 239000006187 pill Substances 0.000 description 1
• 239000004014 plasticizer Substances 0.000 description 1
• 235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 1
• 229920000523 polyvinylpolypyrrolidone Polymers 0.000 description 1
• 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
• 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
• 239000004175 ponceau 4R Substances 0.000 description 1
• 235000012731 ponceau 4R Nutrition 0.000 description 1
• 235000019238 ponceau 6R Nutrition 0.000 description 1
• 235000019237 ponceau SX Nutrition 0.000 description 1
• 229940069328 povidone Drugs 0.000 description 1
• 229960002965 pravastatin Drugs 0.000 description 1
• TUZYXOIXSAXUGO-PZAWKZKUSA-N pravastatin Chemical compound C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 TUZYXOIXSAXUGO-PZAWKZKUSA-N 0.000 description 1
• 238000002953 preparative HPLC Methods 0.000 description 1
• 239000003755 preservative agent Substances 0.000 description 1
• 150000003141 primary amines Chemical class 0.000 description 1
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
• 230000009862 primary prevention Effects 0.000 description 1
• 230000037452 priming Effects 0.000 description 1
• FYPMFJGVHOHGLL-UHFFFAOYSA-N probucol Chemical compound C=1C(C(C)(C)C)=C(O)C(C(C)(C)C)=CC=1SC(C)(C)SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 FYPMFJGVHOHGLL-UHFFFAOYSA-N 0.000 description 1
• 229960003912 probucol Drugs 0.000 description 1
• 230000000069 prophylactic effect Effects 0.000 description 1
• 238000011321 prophylaxis Methods 0.000 description 1
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
• 230000004952 protein activity Effects 0.000 description 1
• 108090000623 proteins and genes Proteins 0.000 description 1
• NITSAQJPBJYMFL-UHFFFAOYSA-N pyridin-4-ol Chemical compound O=C1C=[C]NC=C1 NITSAQJPBJYMFL-UHFFFAOYSA-N 0.000 description 1
• 238000011002 quantification Methods 0.000 description 1
• 239000004172 quinoline yellow Substances 0.000 description 1
• 235000012752 quinoline yellow Nutrition 0.000 description 1
• 150000004060 quinone imines Chemical class 0.000 description 1
• GZUITABIAKMVPG-UHFFFAOYSA-N raloxifene Chemical compound C1=CC(O)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(O)C=C2S1 GZUITABIAKMVPG-UHFFFAOYSA-N 0.000 description 1
• 229960004622 raloxifene Drugs 0.000 description 1
• 208000002574 reactive arthritis Diseases 0.000 description 1
• 230000008707 rearrangement Effects 0.000 description 1
• 238000001953 recrystallisation Methods 0.000 description 1
• 239000004180 red 2G Substances 0.000 description 1
• 235000012739 red 2G Nutrition 0.000 description 1
• 230000001105 regulatory effect Effects 0.000 description 1
• 208000037803 restenosis Diseases 0.000 description 1
• 230000004264 retinal detachment Effects 0.000 description 1
• 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
• 230000002441 reversible effect Effects 0.000 description 1
• 239000002151 riboflavin Substances 0.000 description 1
• 235000019192 riboflavin Nutrition 0.000 description 1
• 235000019234 riboflavin-5-sodium phosphate Nutrition 0.000 description 1
• 238000007363 ring formation reaction Methods 0.000 description 1
• 229940089617 risedronate Drugs 0.000 description 1
• 229960004136 rivastigmine Drugs 0.000 description 1
• 229960004586 rosiglitazone Drugs 0.000 description 1
• 229960001860 salicylate Drugs 0.000 description 1
• 229930195734 saturated hydrocarbon Natural products 0.000 description 1
• 230000009863 secondary prevention Effects 0.000 description 1
• 230000011664 signaling Effects 0.000 description 1
• 239000000741 silica gel Substances 0.000 description 1
• 229910002027 silica gel Inorganic materials 0.000 description 1
• 238000010898 silica gel chromatography Methods 0.000 description 1
• 229960002855 simvastatin Drugs 0.000 description 1
• RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 description 1
• 238000009097 single-agent therapy Methods 0.000 description 1
• 235000010413 sodium alginate Nutrition 0.000 description 1
• 239000000661 sodium alginate Substances 0.000 description 1
• 229940005550 sodium alginate Drugs 0.000 description 1
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
• 235000017557 sodium bicarbonate Nutrition 0.000 description 1
• 239000012279 sodium borohydride Substances 0.000 description 1
• 229910000033 sodium borohydride Inorganic materials 0.000 description 1
• 229910000029 sodium carbonate Inorganic materials 0.000 description 1
• 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
• 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
• 229920003109 sodium starch glycolate Polymers 0.000 description 1
• 239000008109 sodium starch glycolate Substances 0.000 description 1
• 229940079832 sodium starch glycolate Drugs 0.000 description 1
• 239000000600 sorbitol Substances 0.000 description 1
• 235000010356 sorbitol Nutrition 0.000 description 1
• 210000000952 spleen Anatomy 0.000 description 1
• 239000007921 spray Substances 0.000 description 1
• 208000024794 sputum Diseases 0.000 description 1
• 210000003802 sputum Anatomy 0.000 description 1
• 239000003381 stabilizer Substances 0.000 description 1
• 238000010561 standard procedure Methods 0.000 description 1
• 229940114926 stearate Drugs 0.000 description 1
• 239000008117 stearic acid Substances 0.000 description 1
• 210000004500 stellate cell Anatomy 0.000 description 1
• 230000000707 stereoselective effect Effects 0.000 description 1
• 239000008174 sterile solution Substances 0.000 description 1
• 230000000638 stimulation Effects 0.000 description 1
• 238000007920 subcutaneous administration Methods 0.000 description 1
• 238000006467 substitution reaction Methods 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
• 239000005720 sucrose Substances 0.000 description 1
• 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
• 239000004173 sunset yellow FCF Substances 0.000 description 1
• 235000012751 sunset yellow FCF Nutrition 0.000 description 1
• 239000000829 suppository Substances 0.000 description 1
• 239000004094 surface-active agent Substances 0.000 description 1
• 239000000375 suspending agent Substances 0.000 description 1
• 239000003765 sweetening agent Substances 0.000 description 1
• 238000001308 synthesis method Methods 0.000 description 1
• 239000006188 syrup Substances 0.000 description 1
• 235000020357 syrup Nutrition 0.000 description 1
• 201000000596 systemic lupus erythematosus Diseases 0.000 description 1
• 239000003826 tablet Substances 0.000 description 1
• 239000000454 talc Substances 0.000 description 1
• 229910052623 talc Inorganic materials 0.000 description 1
• 235000012222 talc Nutrition 0.000 description 1
• 235000015523 tannic acid Nutrition 0.000 description 1
• LRBQNJMCXXYXIU-NRMVVENXSA-N tannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-NRMVVENXSA-N 0.000 description 1
• 229940033123 tannic acid Drugs 0.000 description 1
• 229920002258 tannic acid Polymers 0.000 description 1
• 229940095064 tartrate Drugs 0.000 description 1
• 239000004149 tartrazine Substances 0.000 description 1
• 235000012756 tartrazine Nutrition 0.000 description 1
• 208000009056 telangiectasis Diseases 0.000 description 1
• OGBMKVWORPGQRR-UMXFMPSGSA-N teriparatide Chemical compound C([C@H](NC(=O)[C@H](CCSC)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@@H](N)CO)C(C)C)[C@@H](C)CC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC=1N=CNC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1N=CNC=1)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)C1=CNC=N1 OGBMKVWORPGQRR-UMXFMPSGSA-N 0.000 description 1
• 229960005460 teriparatide Drugs 0.000 description 1
• TYOXFGCYGAZCMI-SSDOTTSWSA-N tert-butyl (2r)-7-chloro-2-methyl-5-oxo-2,3-dihydroimidazo[1,2-c]pyrimidine-1-carboxylate Chemical compound C([C@H](N1C(=O)OC(C)(C)C)C)N2C1=CC(Cl)=NC2=O TYOXFGCYGAZCMI-SSDOTTSWSA-N 0.000 description 1
• ACZPBXBIHAOOGB-ZDUSSCGKSA-N tert-butyl (2s)-7-[[3,5-difluoro-4-[2-(trifluoromethyl)pyridin-4-yl]oxyphenyl]methoxy]-2-methyl-5-oxo-2,3-dihydroimidazo[1,2-c]pyrimidine-1-carboxylate Chemical compound C([C@@H](N1C(=O)OC(C)(C)C)C)N(C(N=2)=O)C1=CC=2OCC(C=C1F)=CC(F)=C1OC1=CC=NC(C(F)(F)F)=C1 ACZPBXBIHAOOGB-ZDUSSCGKSA-N 0.000 description 1
• UOUFRTFWWBCVPV-UHFFFAOYSA-N tert-butyl 4-(2,4-dioxo-1H-thieno[3,2-d]pyrimidin-3-yl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(CC1)n1c(=O)[nH]c2ccsc2c1=O UOUFRTFWWBCVPV-UHFFFAOYSA-N 0.000 description 1
• WLANBPRGMLKBNA-UHFFFAOYSA-N tert-butyl 7-chloro-5-oxo-2,3-dihydroimidazo[1,2-c]pyrimidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN2C1=CC(Cl)=NC2=O WLANBPRGMLKBNA-UHFFFAOYSA-N 0.000 description 1
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 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
• 238000004809 thin layer chromatography Methods 0.000 description 1
• 150000007970 thio esters Chemical class 0.000 description 1
• 125000003396 thiol group Chemical group [H]S* 0.000 description 1
• 229940034208 thyroxine Drugs 0.000 description 1
• 210000001578 tight junction Anatomy 0.000 description 1
• 230000000451 tissue damage Effects 0.000 description 1
• 231100000827 tissue damage Toxicity 0.000 description 1
• 238000013334 tissue model Methods 0.000 description 1
• 230000017423 tissue regeneration Effects 0.000 description 1
• 238000003325 tomography Methods 0.000 description 1
• 238000011200 topical administration Methods 0.000 description 1
• 230000002110 toxicologic effect Effects 0.000 description 1
• 231100000759 toxicological effect Toxicity 0.000 description 1
• 235000010487 tragacanth Nutrition 0.000 description 1
• 239000000196 tragacanth Substances 0.000 description 1
• 229940116362 tragacanth Drugs 0.000 description 1
• 230000007704 transition Effects 0.000 description 1
• 230000017105 transposition Effects 0.000 description 1
• 229960001641 troglitazone Drugs 0.000 description 1
• GXPHKUHSUJUWKP-UHFFFAOYSA-N troglitazone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O GXPHKUHSUJUWKP-UHFFFAOYSA-N 0.000 description 1
• GXPHKUHSUJUWKP-NTKDMRAZSA-N troglitazone Natural products C([C@@]1(OC=2C(C)=C(C(=C(C)C=2CC1)O)C)C)OC(C=C1)=CC=C1C[C@H]1SC(=O)NC1=O GXPHKUHSUJUWKP-NTKDMRAZSA-N 0.000 description 1
• 229960005486 vaccine Drugs 0.000 description 1
• 229940070710 valerate Drugs 0.000 description 1
• NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
• 231100000216 vascular lesion Toxicity 0.000 description 1
• 238000009423 ventilation Methods 0.000 description 1
• 239000000080 wetting agent Substances 0.000 description 1
• 238000010626 work up procedure Methods 0.000 description 1
• 235000019235 yellow 2G Nutrition 0.000 description 1
• 150000003751 zinc Chemical class 0.000 description 1
• 229910052725 zinc Inorganic materials 0.000 description 1
• 239000011701 zinc Substances 0.000 description 1