SG186872A1 - 5-(biphenyl-4-yl)-3-phenyl-1,2,4-oxadiazolyl derivatives as ligands on the sphingosine 1-phosphate (s1p) receptors - Google Patents

Info

Publication number

SG186872A1

SG186872A1 SG2012096533A SG2012096533A SG186872A1 SG 186872 A1 SG186872 A1 SG 186872A1 SG 2012096533 A SG2012096533 A SG 2012096533A SG 2012096533 A SG2012096533 A SG 2012096533A SG 186872 A1 SG186872 A1 SG 186872A1

Authority

SG

Singapore

Prior art keywords

methyl

tert

butyl

ethyl

formula

Prior art date

2010-07-08

Links

• Espacenet
• Global Dossier
• Discuss

• -1 5-(biphenyl-4-yl)-3-phenyl-1,2,4-oxadiazolyl Chemical class 0.000 title claims description 82
• DUYSYHSSBDVJSM-KRWOKUGFSA-N sphingosine 1-phosphate Chemical compound CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)COP(O)(O)=O DUYSYHSSBDVJSM-KRWOKUGFSA-N 0.000 title claims description 25
• 239000003446 ligand Substances 0.000 title description 4
• 150000001875 compounds Chemical class 0.000 claims abstract description 426
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 12
• 201000006417 multiple sclerosis Diseases 0.000 claims abstract description 8
• 238000000034 method Methods 0.000 claims description 573
• 239000000203 mixture Substances 0.000 claims description 155
• 150000003839 salts Chemical class 0.000 claims description 64
• 229910052757 nitrogen Inorganic materials 0.000 claims description 26
• 239000004480 active ingredient Substances 0.000 claims description 25
• 239000012453 solvate Substances 0.000 claims description 21
• 239000003814 drug Substances 0.000 claims description 18
• 239000002253 acid Substances 0.000 claims description 17
• 239000008194 pharmaceutical composition Substances 0.000 claims description 17
• 125000004432 carbon atom Chemical group C* 0.000 claims description 16
• 238000011282 treatment Methods 0.000 claims description 15
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 13
• 238000002360 preparation method Methods 0.000 claims description 11
• 125000000217 alkyl group Chemical group 0.000 claims description 9
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
• 230000001363 autoimmune Effects 0.000 claims description 7
• 230000004957 immunoregulator effect Effects 0.000 claims description 7
• 230000008569 process Effects 0.000 claims description 7
• 230000005856 abnormality Effects 0.000 claims description 5
• 230000001684 chronic effect Effects 0.000 claims description 5
• 208000035475 disorder Diseases 0.000 claims description 5
• 229910052731 fluorine Inorganic materials 0.000 claims description 5
• 229930182480 glucuronide Natural products 0.000 claims description 5
• 150000008134 glucuronides Chemical class 0.000 claims description 5
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 4
• 102100028651 Tenascin-N Human genes 0.000 claims description 4
• 101710087911 Tenascin-N Proteins 0.000 claims description 4
• 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 4
• 239000003153 chemical reaction reagent Substances 0.000 claims description 4
• 230000028993 immune response Effects 0.000 claims description 4
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
• 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 4
• 208000023275 Autoimmune disease Diseases 0.000 claims description 3
• 239000002671 adjuvant Substances 0.000 claims description 3
• 208000037979 autoimmune inflammatory disease Diseases 0.000 claims description 3
• 208000037976 chronic inflammation Diseases 0.000 claims description 3
• 208000037893 chronic inflammatory disorder Diseases 0.000 claims description 3
• 238000011321 prophylaxis Methods 0.000 claims description 3
• 206010003210 Arteriosclerosis Diseases 0.000 claims description 2
• 201000001320 Atherosclerosis Diseases 0.000 claims description 2
• 206010003827 Autoimmune hepatitis Diseases 0.000 claims description 2
• 206010039710 Scleroderma Diseases 0.000 claims description 2
• 208000011775 arteriosclerosis disease Diseases 0.000 claims description 2
• 238000009833 condensation Methods 0.000 claims description 2
• 230000005494 condensation Effects 0.000 claims description 2
• 238000000926 separation method Methods 0.000 claims 1
• DUYSYHSSBDVJSM-KRWOKUGFSA-M sphingosine 1-phosphate(1-) Chemical compound CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H]([NH3+])COP([O-])([O-])=O DUYSYHSSBDVJSM-KRWOKUGFSA-M 0.000 claims 1
• 201000010099 disease Diseases 0.000 abstract description 7
• 239000003112 inhibitor Substances 0.000 abstract description 3
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 181
• 239000000543 intermediate Substances 0.000 description 172
• 238000004128 high performance liquid chromatography Methods 0.000 description 171
• 238000005481 NMR spectroscopy Methods 0.000 description 162
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 151
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 150
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 114
• 239000000243 solution Substances 0.000 description 104
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 98
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 97
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 95
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 93
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 91
• 239000011541 reaction mixture Substances 0.000 description 88
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 84
• 239000002904 solvent Substances 0.000 description 78
• 235000019439 ethyl acetate Nutrition 0.000 description 77
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 75
• 229910052739 hydrogen Inorganic materials 0.000 description 66
• 239000000843 powder Substances 0.000 description 65
• 239000007787 solid Substances 0.000 description 65
• 235000002639 sodium chloride Nutrition 0.000 description 60
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 55
• QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 50
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 45
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 42
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
• 239000012267 brine Substances 0.000 description 39
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 39
• 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 37
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
• 239000012044 organic layer Substances 0.000 description 36
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 35
• 102100025750 Sphingosine 1-phosphate receptor 1 Human genes 0.000 description 33
• 239000003921 oil Substances 0.000 description 33
• 230000002829 reductive effect Effects 0.000 description 32
• 101710155454 Sphingosine 1-phosphate receptor 1 Proteins 0.000 description 31
• 238000006243 chemical reaction Methods 0.000 description 31
• 235000019198 oils Nutrition 0.000 description 31
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 31
• 102100025747 Sphingosine 1-phosphate receptor 3 Human genes 0.000 description 29
• 101710155457 Sphingosine 1-phosphate receptor 3 Proteins 0.000 description 29
• 239000007788 liquid Substances 0.000 description 29
• 238000003818 flash chromatography Methods 0.000 description 27
• 239000012230 colorless oil Substances 0.000 description 26
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 25
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 23
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 23
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 22
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 22
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 22
• 150000001412 amines Chemical class 0.000 description 22
• 239000002585 base Substances 0.000 description 21
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 20
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 19
• 239000006260 foam Substances 0.000 description 19
• 238000009472 formulation Methods 0.000 description 19
• 229910052760 oxygen Inorganic materials 0.000 description 19
• 238000000746 purification Methods 0.000 description 19
• SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 description 18
• PYFSLJVSCGXYAJ-UHFFFAOYSA-N methyl 2-hydroxy-4-[[3-(2-hydroxyphenyl)phenyl]sulfonylamino]benzoate Chemical compound C1=C(O)C(C(=O)OC)=CC=C1NS(=O)(=O)C1=CC=CC(C=2C(=CC=CC=2)O)=C1 PYFSLJVSCGXYAJ-UHFFFAOYSA-N 0.000 description 18
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
• 239000012074 organic phase Substances 0.000 description 18
• 239000007864 aqueous solution Substances 0.000 description 17
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 16
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 16
• 150000002148 esters Chemical class 0.000 description 16
• 239000010410 layer Substances 0.000 description 16
• 102000005962 receptors Human genes 0.000 description 16
• 108020003175 receptors Proteins 0.000 description 16
• XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 15
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 15
• 241000699666 Mus <mouse, genus> Species 0.000 description 15
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 15
• 229960000583 acetic acid Drugs 0.000 description 15
• 239000003826 tablet Substances 0.000 description 15
• AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 14
• DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 description 14
• 102000011011 Sphingosine 1-phosphate receptors Human genes 0.000 description 14
• 108050001083 Sphingosine 1-phosphate receptors Proteins 0.000 description 14
• 239000003480 eluent Substances 0.000 description 14
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
• 230000015572 biosynthetic process Effects 0.000 description 13
• 235000019253 formic acid Nutrition 0.000 description 13
• 239000003208 petroleum Substances 0.000 description 13
• 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 12
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 12
• 239000003795 chemical substances by application Substances 0.000 description 12
• 229910052801 chlorine Inorganic materials 0.000 description 12
• 239000002207 metabolite Substances 0.000 description 12
• 238000001556 precipitation Methods 0.000 description 12
• 238000004296 chiral HPLC Methods 0.000 description 11
• 239000000706 filtrate Substances 0.000 description 11
• 230000002209 hydrophobic effect Effects 0.000 description 11
• 235000017557 sodium bicarbonate Nutrition 0.000 description 11
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 11
• ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 10
• 229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 10
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 10
• 239000000556 agonist Substances 0.000 description 10
• 150000001298 alcohols Chemical class 0.000 description 10
• 235000012538 ammonium bicarbonate Nutrition 0.000 description 10
• 239000001099 ammonium carbonate Substances 0.000 description 10
• 210000004027 cell Anatomy 0.000 description 10
• 238000004440 column chromatography Methods 0.000 description 10
• 239000012043 crude product Substances 0.000 description 10
• 150000004866 oxadiazoles Chemical class 0.000 description 10
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
• 239000012047 saturated solution Substances 0.000 description 10
• BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 10
• 238000003786 synthesis reaction Methods 0.000 description 10
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 9
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 9
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
• 208000006673 asthma Diseases 0.000 description 9
• 238000002844 melting Methods 0.000 description 9
• 230000008018 melting Effects 0.000 description 9
• 239000012279 sodium borohydride Substances 0.000 description 9
• 229910000033 sodium borohydride Inorganic materials 0.000 description 9
• 239000007858 starting material Substances 0.000 description 9
• 229910052727 yttrium Inorganic materials 0.000 description 9
• ZESZAIOGACKOMB-UHFFFAOYSA-N 4-(bromomethyl)-3-fluorobenzonitrile Chemical compound FC1=CC(C#N)=CC=C1CBr ZESZAIOGACKOMB-UHFFFAOYSA-N 0.000 description 8
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 8
• 229940024606 amino acid Drugs 0.000 description 8
• 235000001014 amino acid Nutrition 0.000 description 8
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
• 239000002244 precipitate Substances 0.000 description 8
• 125000006239 protecting group Chemical group 0.000 description 8
• 239000000725 suspension Substances 0.000 description 8
• 239000003643 water by type Substances 0.000 description 8
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 7
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 7
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 7
• 241000699670 Mus sp. Species 0.000 description 7
• 206010033799 Paralysis Diseases 0.000 description 7
• 150000001413 amino acids Chemical class 0.000 description 7
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 7
• 239000002775 capsule Substances 0.000 description 7
• 238000001704 evaporation Methods 0.000 description 7
• 230000008020 evaporation Effects 0.000 description 7
• 125000001841 imino group Chemical group [H]N=* 0.000 description 7
• 239000012442 inert solvent Substances 0.000 description 7
• 150000002825 nitriles Chemical class 0.000 description 7
• 230000037361 pathway Effects 0.000 description 7
• 229910000027 potassium carbonate Inorganic materials 0.000 description 7
• 238000002953 preparative HPLC Methods 0.000 description 7
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
• 238000010992 reflux Methods 0.000 description 7
• VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 7
• 229940086542 triethylamine Drugs 0.000 description 7
• PAQZWJGSJMLPMG-UHFFFAOYSA-N 2,4,6-tripropyl-1,3,5,2$l^{5},4$l^{5},6$l^{5}-trioxatriphosphinane 2,4,6-trioxide Chemical compound CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1 PAQZWJGSJMLPMG-UHFFFAOYSA-N 0.000 description 6
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 6
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
• FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 6
• QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
• 125000002252 acyl group Chemical group 0.000 description 6
• 150000001299 aldehydes Chemical class 0.000 description 6
• 239000011230 binding agent Substances 0.000 description 6
• 239000013058 crude material Substances 0.000 description 6
• 239000012458 free base Substances 0.000 description 6
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
• XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
• 239000000314 lubricant Substances 0.000 description 6
• 238000004949 mass spectrometry Methods 0.000 description 6
• CCLBEXAGIJGEMC-DTIOYNMSSA-N methyl (2s)-2-[1-(3-cyanophenyl)ethyl-methylamino]propanoate Chemical compound COC(=O)[C@H](C)N(C)C(C)C1=CC=CC(C#N)=C1 CCLBEXAGIJGEMC-DTIOYNMSSA-N 0.000 description 6
• OEUDXUZQFRROTN-ZJUUUORDSA-N methyl (2s)-2-[[(1r)-1-(4-cyanophenyl)ethyl]amino]propanoate Chemical compound COC(=O)[C@H](C)N[C@H](C)C1=CC=C(C#N)C=C1 OEUDXUZQFRROTN-ZJUUUORDSA-N 0.000 description 6
• ACEONLNNWKIPTM-UHFFFAOYSA-N methyl 2-bromopropanoate Chemical compound COC(=O)C(C)Br ACEONLNNWKIPTM-UHFFFAOYSA-N 0.000 description 6
• QSRRZKPKHJHIRB-UHFFFAOYSA-N methyl 4-[(2,5-dichloro-4-methylthiophen-3-yl)sulfonylamino]-2-hydroxybenzoate Chemical compound C1=C(O)C(C(=O)OC)=CC=C1NS(=O)(=O)C1=C(Cl)SC(Cl)=C1C QSRRZKPKHJHIRB-UHFFFAOYSA-N 0.000 description 6
• 239000012299 nitrogen atmosphere Substances 0.000 description 6
• WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 6
• VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 6
• 239000011734 sodium Substances 0.000 description 6
• 238000003756 stirring Methods 0.000 description 6
• 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 6
• YQIKHHMKHKRGAI-UHFFFAOYSA-N tert-butyl 2-[(4-cyano-2-fluorophenyl)methylamino]-2-methylpropanoate Chemical compound CC(C)(C)OC(=O)C(C)(C)NCC1=CC=C(C#N)C=C1F YQIKHHMKHKRGAI-UHFFFAOYSA-N 0.000 description 6
• VEEVWDCVXOWCBA-UHFFFAOYSA-N tert-butyl 2-[[2-fluoro-4-[(e)-n'-hydroxycarbamimidoyl]phenyl]methyl-methylamino]-2-methylpropanoate Chemical compound CC(C)(C)OC(=O)C(C)(C)N(C)CC1=CC=C(C(N)=NO)C=C1F VEEVWDCVXOWCBA-UHFFFAOYSA-N 0.000 description 6
• LSMXDZJZKNRIPQ-UHFFFAOYSA-N tert-butyl 2-[[2-fluoro-4-[(e)-n'-hydroxycarbamimidoyl]phenyl]methylamino]-2-methylpropanoate Chemical compound CC(C)(C)OC(=O)C(C)(C)NCC1=CC=C(C(N)=NO)C=C1F LSMXDZJZKNRIPQ-UHFFFAOYSA-N 0.000 description 6
• BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 6
• FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 6
• LZHZRUMDTRUWCF-UHFFFAOYSA-N 1-[4-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethanol Chemical compound C1=CC(C(O)C)=CC=C1C1=NOC(C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=N1 LZHZRUMDTRUWCF-UHFFFAOYSA-N 0.000 description 5
• NLPHXWGWBKZSJC-UHFFFAOYSA-N 4-acetylbenzonitrile Chemical compound CC(=O)C1=CC=C(C#N)C=C1 NLPHXWGWBKZSJC-UHFFFAOYSA-N 0.000 description 5
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
• WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 5
• 201000004624 Dermatitis Diseases 0.000 description 5
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 5
• 241001465754 Metazoa Species 0.000 description 5
• MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 5
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 5
• 229920002472 Starch Polymers 0.000 description 5
• 239000000908 ammonium hydroxide Substances 0.000 description 5
• 239000012298 atmosphere Substances 0.000 description 5
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 5
• 239000000872 buffer Substances 0.000 description 5
• 229910002091 carbon monoxide Inorganic materials 0.000 description 5
• 238000004587 chromatography analysis Methods 0.000 description 5
• 239000006071 cream Substances 0.000 description 5
• 229920000159 gelatin Polymers 0.000 description 5
• 235000019322 gelatine Nutrition 0.000 description 5
• 230000007062 hydrolysis Effects 0.000 description 5
• 238000006460 hydrolysis reaction Methods 0.000 description 5
• 150000002576 ketones Chemical class 0.000 description 5
• OEUDXUZQFRROTN-NXEZZACHSA-N methyl (2r)-2-[[(1r)-1-(4-cyanophenyl)ethyl]amino]propanoate Chemical compound COC(=O)[C@@H](C)N[C@H](C)C1=CC=C(C#N)C=C1 OEUDXUZQFRROTN-NXEZZACHSA-N 0.000 description 5
• OEUDXUZQFRROTN-VHSXEESVSA-N methyl (2r)-2-[[(1s)-1-(4-cyanophenyl)ethyl]amino]propanoate Chemical compound COC(=O)[C@@H](C)N[C@@H](C)C1=CC=C(C#N)C=C1 OEUDXUZQFRROTN-VHSXEESVSA-N 0.000 description 5
• YGDGZDGRCWHDOU-UHFFFAOYSA-N methyl 4-[[5-chloro-4-(2-hydroxyphenyl)thiophen-2-yl]sulfonylamino]-2-hydroxybenzoate Chemical group C1=C(O)C(C(=O)OC)=CC=C1NS(=O)(=O)C1=CC(C=2C(=CC=CC=2)O)=C(Cl)S1 YGDGZDGRCWHDOU-UHFFFAOYSA-N 0.000 description 5
• 239000000047 product Substances 0.000 description 5
• 230000000630 rising effect Effects 0.000 description 5
• 239000011780 sodium chloride Substances 0.000 description 5
• 235000019698 starch Nutrition 0.000 description 5
• 239000008107 starch Substances 0.000 description 5
• 239000000126 substance Substances 0.000 description 5
• KTQLOPNHSRZIHW-UHFFFAOYSA-N tert-butyl 2-[(4-cyano-2-fluorophenyl)methylamino]-3-methylbutanoate Chemical compound CC(C)(C)OC(=O)C(C(C)C)NCC1=CC=C(C#N)C=C1F KTQLOPNHSRZIHW-UHFFFAOYSA-N 0.000 description 5
• IVIQFUCVLFGGLB-UHFFFAOYSA-N tert-butyl 2-[1-(4-cyanophenyl)ethyl-methylamino]acetate Chemical compound CC(C)(C)OC(=O)CN(C)C(C)C1=CC=C(C#N)C=C1 IVIQFUCVLFGGLB-UHFFFAOYSA-N 0.000 description 5
• ACZCUMNKRUGMDJ-LLVKDONJSA-N tert-butyl 2-[[(1r)-1-[4-[(e)-n'-hydroxycarbamimidoyl]phenyl]ethyl]-methylamino]acetate Chemical compound CC(C)(C)OC(=O)CN(C)[C@H](C)C1=CC=C(C(N)=NO)C=C1 ACZCUMNKRUGMDJ-LLVKDONJSA-N 0.000 description 5
• NBKZGRPRTQELKX-UHFFFAOYSA-N (2-methylpropan-2-yl)oxymethanone Chemical compound CC(C)(C)O[C]=O NBKZGRPRTQELKX-UHFFFAOYSA-N 0.000 description 4
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
• YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 4
• HCGNPQRUNHMUDF-UHFFFAOYSA-N 3-fluoro-4-(methylaminomethyl)benzonitrile Chemical compound CNCC1=CC=C(C#N)C=C1F HCGNPQRUNHMUDF-UHFFFAOYSA-N 0.000 description 4
• CGYNMXWYNFMIPM-UHFFFAOYSA-N 4-(2-hydroxyacetyl)benzonitrile Chemical compound OCC(=O)C1=CC=C(C#N)C=C1 CGYNMXWYNFMIPM-UHFFFAOYSA-N 0.000 description 4
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
• PCBZRNYXXCIELG-WYFCWLEVSA-N COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 Chemical compound COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 PCBZRNYXXCIELG-WYFCWLEVSA-N 0.000 description 4
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
• 239000007821 HATU Substances 0.000 description 4
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
• 229910019142 PO4 Inorganic materials 0.000 description 4
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
• 206010046851 Uveitis Diseases 0.000 description 4
• 150000007513 acids Chemical class 0.000 description 4
• 150000001408 amides Chemical class 0.000 description 4
• 239000008346 aqueous phase Substances 0.000 description 4
• HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
• JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 4
• SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 4
• 150000003939 benzylamines Chemical class 0.000 description 4
• 229910052794 bromium Inorganic materials 0.000 description 4
• 229910052799 carbon Inorganic materials 0.000 description 4
• 150000001735 carboxylic acids Chemical class 0.000 description 4
• 238000005859 coupling reaction Methods 0.000 description 4
• ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 4
• 229940043237 diethanolamine Drugs 0.000 description 4
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 4
• LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 4
• 239000007884 disintegrant Substances 0.000 description 4
• 239000000975 dye Substances 0.000 description 4
• 239000012039 electrophile Substances 0.000 description 4
• 238000000132 electrospray ionisation Methods 0.000 description 4
• 238000000921 elemental analysis Methods 0.000 description 4
• 238000005516 engineering process Methods 0.000 description 4
• 229960000556 fingolimod Drugs 0.000 description 4
• KKGQTZUTZRNORY-UHFFFAOYSA-N fingolimod Chemical compound CCCCCCCCC1=CC=C(CCC(N)(CO)CO)C=C1 KKGQTZUTZRNORY-UHFFFAOYSA-N 0.000 description 4
• 239000000796 flavoring agent Substances 0.000 description 4
• 235000019634 flavors Nutrition 0.000 description 4
• 125000005519 fluorenylmethyloxycarbonyl group Chemical group 0.000 description 4
• BRZYSWJRSDMWLG-CAXSIQPQSA-N geneticin Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](C(C)O)O2)N)[C@@H](N)C[C@H]1N BRZYSWJRSDMWLG-CAXSIQPQSA-N 0.000 description 4
• KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 4
• 239000008187 granular material Substances 0.000 description 4
• 239000001257 hydrogen Substances 0.000 description 4
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 4
• 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 description 4
• 230000001506 immunosuppresive effect Effects 0.000 description 4
• 238000002347 injection Methods 0.000 description 4
• 239000007924 injection Substances 0.000 description 4
• JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropyl acetate Chemical compound CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 4
• 210000003141 lower extremity Anatomy 0.000 description 4
• 235000019359 magnesium stearate Nutrition 0.000 description 4
• 239000012528 membrane Substances 0.000 description 4
• 229910052751 metal Inorganic materials 0.000 description 4
• 239000002184 metal Substances 0.000 description 4
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
• BFJZMJAOSJIUMC-QZTJIDSGSA-N methyl (2r)-2-[[(1r)-1-[4-[5-[3-methyl-4-[2-(trifluoromethyl)phenyl]phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]amino]propanoate Chemical compound C1=CC([C@@H](C)N[C@H](C)C(=O)OC)=CC=C1C1=NOC(C=2C=C(C)C(=CC=2)C=2C(=CC=CC=2)C(F)(F)F)=N1 BFJZMJAOSJIUMC-QZTJIDSGSA-N 0.000 description 4
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 4
• LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
• 231100000252 nontoxic Toxicity 0.000 description 4
• 230000003000 nontoxic effect Effects 0.000 description 4
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
• 239000010452 phosphate Substances 0.000 description 4
• 239000002953 phosphate buffered saline Substances 0.000 description 4
• 229920000642 polymer Polymers 0.000 description 4
• 238000003825 pressing Methods 0.000 description 4
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
• 238000007363 ring formation reaction Methods 0.000 description 4
• 201000000306 sarcoidosis Diseases 0.000 description 4
• 229920006395 saturated elastomer Polymers 0.000 description 4
• QFJCIRLUMZQUOT-HPLJOQBZSA-N sirolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 description 4
• 229960002930 sirolimus Drugs 0.000 description 4
• PAWKLFLVSVNNPA-UHFFFAOYSA-N tert-butyl 2-[(2-fluoro-4-isocyanophenyl)methyl-methylamino]-2-methylpropanoate Chemical compound CC(C)(C)OC(=O)C(C)(C)N(C)CC1=CC=C([N+]#[C-])C=C1F PAWKLFLVSVNNPA-UHFFFAOYSA-N 0.000 description 4
• SJMDMGHPMLKLHQ-UHFFFAOYSA-N tert-butyl 2-aminoacetate Chemical compound CC(C)(C)OC(=O)CN SJMDMGHPMLKLHQ-UHFFFAOYSA-N 0.000 description 4
• 238000012360 testing method Methods 0.000 description 4
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
• LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 4
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 3
• QWCKQJZIFLGMSD-UHFFFAOYSA-N 2-Aminobutanoic acid Natural products CCC(N)C(O)=O QWCKQJZIFLGMSD-UHFFFAOYSA-N 0.000 description 3
• IVLXQGJVBGMLRR-UHFFFAOYSA-N 2-aminoacetic acid;hydron;chloride Chemical class Cl.NCC(O)=O IVLXQGJVBGMLRR-UHFFFAOYSA-N 0.000 description 3
• YMNGMGLZWKUGGJ-UHFFFAOYSA-N 3-(methoxymethyl)-4-(2-methylphenyl)benzoic acid Chemical compound COCC1=CC(C(O)=O)=CC=C1C1=CC=CC=C1C YMNGMGLZWKUGGJ-UHFFFAOYSA-N 0.000 description 3
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
• BVGWYOPERDHROG-UHFFFAOYSA-N 4-[2-(difluoromethyl)phenyl]-3-methylbenzoic acid Chemical compound CC1=CC(C(O)=O)=CC=C1C1=CC=CC=C1C(F)F BVGWYOPERDHROG-UHFFFAOYSA-N 0.000 description 3
• OOJCPHNFLMBMNG-UHFFFAOYSA-N 4-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]benzaldehyde Chemical compound CC1=CC=CC=C1C1=CC=C(C=2ON=C(N=2)C=2C=CC(C=O)=CC=2)C=C1C(F)(F)F OOJCPHNFLMBMNG-UHFFFAOYSA-N 0.000 description 3
• 208000008439 Biliary Liver Cirrhosis Diseases 0.000 description 3
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
• VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 3
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
• KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 3
• 206010009900 Colitis ulcerative Diseases 0.000 description 3
• 208000011231 Crohn disease Diseases 0.000 description 3
• QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 3
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
• 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 3
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 3
• PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
• 239000001828 Gelatine Substances 0.000 description 3
• 206010018364 Glomerulonephritis Diseases 0.000 description 3
• 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 3
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
• 206010019663 Hepatic failure Diseases 0.000 description 3
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
• QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 3
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
• GDFAOVXKHJXLEI-VKHMYHEASA-N N-methyl-L-alanine Chemical compound C[NH2+][C@@H](C)C([O-])=O GDFAOVXKHJXLEI-VKHMYHEASA-N 0.000 description 3
• 229910002651 NO3 Inorganic materials 0.000 description 3
• NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 3
• 206010034277 Pemphigoid Diseases 0.000 description 3
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
• 201000004681 Psoriasis Diseases 0.000 description 3
• 229930006000 Sucrose Natural products 0.000 description 3
• 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 3
• QJJXYPPXXYFBGM-LFZNUXCKSA-N Tacrolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1\C=C(/C)[C@@H]1[C@H](C)[C@@H](O)CC(=O)[C@H](CC=C)/C=C(C)/C[C@H](C)C[C@H](OC)[C@H]([C@H](C[C@H]2C)OC)O[C@@]2(O)C(=O)C(=O)N2CCCC[C@H]2C(=O)O1 QJJXYPPXXYFBGM-LFZNUXCKSA-N 0.000 description 3
• 201000006704 Ulcerative Colitis Diseases 0.000 description 3
• KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 3
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
• 238000004458 analytical method Methods 0.000 description 3
• 125000003118 aryl group Chemical group 0.000 description 3
• 238000003556 assay Methods 0.000 description 3
• 239000011324 bead Substances 0.000 description 3
• AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical class BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 3
• 230000037396 body weight Effects 0.000 description 3
• 208000000594 bullous pemphigoid Diseases 0.000 description 3
• 229910052791 calcium Inorganic materials 0.000 description 3
• 239000011575 calcium Substances 0.000 description 3
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
• 239000001768 carboxy methyl cellulose Substances 0.000 description 3
• 239000003054 catalyst Substances 0.000 description 3
• OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 3
• 229960001231 choline Drugs 0.000 description 3
• 125000000753 cycloalkyl group Chemical group 0.000 description 3
• 206010012601 diabetes mellitus Diseases 0.000 description 3
• 229940079593 drug Drugs 0.000 description 3
• 230000000694 effects Effects 0.000 description 3
• 239000000839 emulsion Substances 0.000 description 3
• 150000002170 ethers Chemical class 0.000 description 3
• 229940012017 ethylenediamine Drugs 0.000 description 3
• 210000003414 extremity Anatomy 0.000 description 3
• 239000008103 glucose Substances 0.000 description 3
• 210000003128 head Anatomy 0.000 description 3
• 238000007327 hydrogenolysis reaction Methods 0.000 description 3
• 206010021198 ichthyosis Diseases 0.000 description 3
• SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 3
• 210000000265 leukocyte Anatomy 0.000 description 3
• 208000007903 liver failure Diseases 0.000 description 3
• 231100000835 liver failure Toxicity 0.000 description 3
• 210000004698 lymphocyte Anatomy 0.000 description 3
• 229910052749 magnesium Inorganic materials 0.000 description 3
• 239000011777 magnesium Substances 0.000 description 3
• 229910000000 metal hydroxide Inorganic materials 0.000 description 3
• 150000004692 metal hydroxides Chemical class 0.000 description 3
• PTTKIDGCCBNXRF-DTWKUNHWSA-N methyl (2r)-2-[[(1s)-1-[4-[(z)-n'-hydroxycarbamimidoyl]phenyl]ethyl]amino]propanoate Chemical compound COC(=O)[C@@H](C)N[C@@H](C)C1=CC=C(C(=N)NO)C=C1 PTTKIDGCCBNXRF-DTWKUNHWSA-N 0.000 description 3
• LUVNJSXHNGHIPF-ZWKOTPCHSA-N methyl (2r)-2-[[(1s)-1-[4-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]amino]propanoate Chemical compound C1=CC([C@H](C)N[C@H](C)C(=O)OC)=CC=C1C1=NOC(C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=N1 LUVNJSXHNGHIPF-ZWKOTPCHSA-N 0.000 description 3
• VSJNWVCUBPAENV-DTIOYNMSSA-N methyl (2s)-2-[1-(4-cyanophenyl)ethyl-methylamino]propanoate Chemical compound COC(=O)[C@H](C)N(C)C(C)C1=CC=C(C#N)C=C1 VSJNWVCUBPAENV-DTIOYNMSSA-N 0.000 description 3
• YJFJMOOSRBBWNB-AXDSSHIGSA-N methyl (2s)-2-[1-[3-[(z)-n'-hydroxycarbamimidoyl]phenyl]ethyl-methylamino]propanoate Chemical compound COC(=O)[C@H](C)N(C)C(C)C1=CC=CC(C(=N)NO)=C1 YJFJMOOSRBBWNB-AXDSSHIGSA-N 0.000 description 3
• ONWQZOKMWGZUBW-AXDSSHIGSA-N methyl (2s)-2-[1-[4-(n'-hydroxycarbamimidoyl)phenyl]ethyl-methylamino]propanoate Chemical compound COC(=O)[C@H](C)N(C)C(C)C1=CC=C(C(N)=NO)C=C1 ONWQZOKMWGZUBW-AXDSSHIGSA-N 0.000 description 3
• OEUDXUZQFRROTN-UWVGGRQHSA-N methyl (2s)-2-[[(1s)-1-(4-cyanophenyl)ethyl]amino]propanoate Chemical compound COC(=O)[C@H](C)N[C@@H](C)C1=CC=C(C#N)C=C1 OEUDXUZQFRROTN-UWVGGRQHSA-N 0.000 description 3
• 150000007522 mineralic acids Chemical class 0.000 description 3
• QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
• 210000000056 organ Anatomy 0.000 description 3
• 150000007524 organic acids Chemical class 0.000 description 3
• 239000006072 paste Substances 0.000 description 3
• LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 3
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
• 229910052700 potassium Inorganic materials 0.000 description 3
• 239000011591 potassium Substances 0.000 description 3
• 150000003254 radicals Chemical class 0.000 description 3
• 238000006268 reductive amination reaction Methods 0.000 description 3
• 238000004007 reversed phase HPLC Methods 0.000 description 3
• 239000000377 silicon dioxide Substances 0.000 description 3
• 229910052708 sodium Inorganic materials 0.000 description 3
• 235000015424 sodium Nutrition 0.000 description 3
• 229910052938 sodium sulfate Inorganic materials 0.000 description 3
• 235000011152 sodium sulphate Nutrition 0.000 description 3
• 239000005720 sucrose Substances 0.000 description 3
• 235000000346 sugar Nutrition 0.000 description 3
• 238000004808 supercritical fluid chromatography Methods 0.000 description 3
• 239000006188 syrup Substances 0.000 description 3
• 235000020357 syrup Nutrition 0.000 description 3
• QJJXYPPXXYFBGM-SHYZHZOCSA-N tacrolimus Natural products CO[C@H]1C[C@H](CC[C@@H]1O)C=C(C)[C@H]2OC(=O)[C@H]3CCCCN3C(=O)C(=O)[C@@]4(O)O[C@@H]([C@H](C[C@H]4C)OC)[C@@H](C[C@H](C)CC(=C[C@@H](CC=C)C(=O)C[C@H](O)[C@H]2C)C)OC QJJXYPPXXYFBGM-SHYZHZOCSA-N 0.000 description 3
• OMHCLHIWCBYVQP-UHFFFAOYSA-N tert-butyl 2-[(2-fluoro-4-isocyanophenyl)methyl-methylamino]butanoate Chemical compound CC(C)(C)OC(=O)C(CC)N(C)CC1=CC=C([N+]#[C-])C=C1F OMHCLHIWCBYVQP-UHFFFAOYSA-N 0.000 description 3
• DRUGLDXGMFFYMK-UHFFFAOYSA-N tert-butyl 2-[(3-cyano-5-fluorophenyl)methylamino]-2-methylpropanoate Chemical compound CC(C)(C)OC(=O)C(C)(C)NCC1=CC(F)=CC(C#N)=C1 DRUGLDXGMFFYMK-UHFFFAOYSA-N 0.000 description 3
• JZOBAXQZAHIFSC-UHFFFAOYSA-N tert-butyl 2-[(3-cyano-5-fluorophenyl)methylamino]-4-methylpentanoate Chemical compound CC(C)(C)OC(=O)C(CC(C)C)NCC1=CC(F)=CC(C#N)=C1 JZOBAXQZAHIFSC-UHFFFAOYSA-N 0.000 description 3
• MUMVLEWLOTZJOL-UHFFFAOYSA-N tert-butyl 2-[(4-cyano-2-fluorophenyl)methyl-methylamino]-3-methylbutanoate Chemical compound CC(C)(C)OC(=O)C(C(C)C)N(C)CC1=CC=C(C#N)C=C1F MUMVLEWLOTZJOL-UHFFFAOYSA-N 0.000 description 3
• RWNSSLDFNUBVTA-UHFFFAOYSA-N tert-butyl 2-[(4-cyano-2-fluorophenyl)methyl-methylamino]propanoate Chemical compound CC(C)(C)OC(=O)C(C)N(C)CC1=CC=C(C#N)C=C1F RWNSSLDFNUBVTA-UHFFFAOYSA-N 0.000 description 3
• XPCZULFHCCPGRY-UHFFFAOYSA-N tert-butyl 2-[(4-cyano-2-fluorophenyl)methylamino]butanoate Chemical compound CC(C)(C)OC(=O)C(CC)NCC1=CC=C(C#N)C=C1F XPCZULFHCCPGRY-UHFFFAOYSA-N 0.000 description 3
• PRYVBGSLLFOVKD-LLVKDONJSA-N tert-butyl 2-[[(1r)-1-(4-cyanophenyl)ethyl]amino]acetate Chemical compound CC(C)(C)OC(=O)CN[C@H](C)C1=CC=C(C#N)C=C1 PRYVBGSLLFOVKD-LLVKDONJSA-N 0.000 description 3
• WQUMKKZGTBTZHO-UHFFFAOYSA-N tert-butyl 2-[[1-(4-cyanophenyl)-2-methoxyethyl]-methylamino]acetate Chemical compound CC(C)(C)OC(=O)CN(C)C(COC)C1=CC=C(C#N)C=C1 WQUMKKZGTBTZHO-UHFFFAOYSA-N 0.000 description 3
• FSEXPFJGAVNTNY-UHFFFAOYSA-N tert-butyl 2-[[2-[tert-butyl(dimethyl)silyl]oxy-1-(4-cyanophenyl)ethyl]amino]acetate Chemical compound CC(C)(C)OC(=O)CNC(CO[Si](C)(C)C(C)(C)C)C1=CC=C(C#N)C=C1 FSEXPFJGAVNTNY-UHFFFAOYSA-N 0.000 description 3
• RKFOZWKWQHFNGA-UHFFFAOYSA-N tert-butyl 2-[[2-[tert-butyl(dimethyl)silyl]oxy-1-[4-(n'-hydroxycarbamimidoyl)phenyl]ethyl]amino]acetate Chemical compound CC(C)(C)OC(=O)CNC(CO[Si](C)(C)C(C)(C)C)C1=CC=C(C(N)=NO)C=C1 RKFOZWKWQHFNGA-UHFFFAOYSA-N 0.000 description 3
• JNEQZIFNJCZPGH-UHFFFAOYSA-N tert-butyl 2-[[2-fluoro-4-[(e)-n'-hydroxycarbamimidoyl]phenyl]methyl-methylamino]propanoate Chemical compound CC(C)(C)OC(=O)C(C)N(C)CC1=CC=C(C(N)=NO)C=C1F JNEQZIFNJCZPGH-UHFFFAOYSA-N 0.000 description 3
• XQJUOTDISDDWTN-UHFFFAOYSA-N tert-butyl 2-[[2-fluoro-4-[(e)-n'-hydroxycarbamimidoyl]phenyl]methylamino]-3-methylbutanoate Chemical compound CC(C)(C)OC(=O)C(C(C)C)NCC1=CC=C(C(N)=NO)C=C1F XQJUOTDISDDWTN-UHFFFAOYSA-N 0.000 description 3
• KJLWLXSAVXNACT-UHFFFAOYSA-N tert-butyl 2-[[3-fluoro-5-[(e)-n'-hydroxycarbamimidoyl]phenyl]methylamino]-2-methylpropanoate Chemical compound CC(C)(C)OC(=O)C(C)(C)NCC1=CC(F)=CC(C(N)=NO)=C1 KJLWLXSAVXNACT-UHFFFAOYSA-N 0.000 description 3
• LSVYCJILORYVCD-UHFFFAOYSA-N tert-butyl 2-amino-2-methylpropanoate Chemical compound CC(C)(C)OC(=O)C(C)(C)N LSVYCJILORYVCD-UHFFFAOYSA-N 0.000 description 3
• RJBVJBGFJIHJSZ-UHFFFAOYSA-N tert-butyl 2-amino-3-methylbutanoate Chemical compound CC(C)C(N)C(=O)OC(C)(C)C RJBVJBGFJIHJSZ-UHFFFAOYSA-N 0.000 description 3
• IGVNJALYNQVQIT-UHFFFAOYSA-N tert-butyl 2-bromo-2-methylpropanoate Chemical compound CC(C)(C)OC(=O)C(C)(C)Br IGVNJALYNQVQIT-UHFFFAOYSA-N 0.000 description 3
• SUOSOBLQTPQGEB-UHFFFAOYSA-N tert-butyl n-[1-[4-(n'-hydroxycarbamimidoyl)phenyl]ethyl]carbamate Chemical compound CC(C)(C)OC(=O)NC(C)C1=CC=C(C(N)=NO)C=C1 SUOSOBLQTPQGEB-UHFFFAOYSA-N 0.000 description 3
• 230000001225 therapeutic effect Effects 0.000 description 3
• 210000001519 tissue Anatomy 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
• 230000000699 topical effect Effects 0.000 description 3
• 238000002054 transplantation Methods 0.000 description 3
• 229960000281 trometamol Drugs 0.000 description 3
• 239000001993 wax Substances 0.000 description 3
• WWUZIQQURGPMPG-UHFFFAOYSA-N (-)-D-erythro-Sphingosine Natural products CCCCCCCCCCCCCC=CC(O)C(N)CO WWUZIQQURGPMPG-UHFFFAOYSA-N 0.000 description 2
• NSJVYHOPHZMZPN-UHFFFAOYSA-N (2-methylphenyl)boronic acid Chemical compound CC1=CC=CC=C1B(O)O NSJVYHOPHZMZPN-UHFFFAOYSA-N 0.000 description 2
• IGSXENUQJGMLDD-IAGOWNOFSA-N (2r)-2-[[(1r)-1-[4-[5-[3-methyl-4-[2-(trifluoromethyl)phenyl]phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]amino]propanoic acid Chemical compound C1=CC([C@@H](C)N[C@H](C)C(O)=O)=CC=C1C1=NOC(C=2C=C(C)C(=CC=2)C=2C(=CC=CC=2)C(F)(F)F)=N1 IGSXENUQJGMLDD-IAGOWNOFSA-N 0.000 description 2
• KQRJZUQGFXNPIF-IAGOWNOFSA-N (2r)-2-[[(1r)-1-[4-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]amino]propanoic acid Chemical compound C1=CC([C@@H](C)N[C@H](C)C(O)=O)=CC=C1C1=NOC(C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=N1 KQRJZUQGFXNPIF-IAGOWNOFSA-N 0.000 description 2
• IGSXENUQJGMLDD-DLBZAZTESA-N (2r)-2-[[(1s)-1-[4-[5-[3-methyl-4-[2-(trifluoromethyl)phenyl]phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]amino]propanoic acid Chemical compound C1=CC([C@H](C)N[C@H](C)C(O)=O)=CC=C1C1=NOC(C=2C=C(C)C(=CC=2)C=2C(=CC=CC=2)C(F)(F)F)=N1 IGSXENUQJGMLDD-DLBZAZTESA-N 0.000 description 2
• KQRJZUQGFXNPIF-DLBZAZTESA-N (2r)-2-[[(1s)-1-[4-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]amino]propanoic acid Chemical compound C1=CC([C@H](C)N[C@H](C)C(O)=O)=CC=C1C1=NOC(C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=N1 KQRJZUQGFXNPIF-DLBZAZTESA-N 0.000 description 2
• VXEOCIWIHSJRHE-WAIKUNEKSA-N (2r)-2-[[(1s)-2-hydroxy-1-[4-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]amino]propanoic acid Chemical compound C1=CC([C@@H](CO)N[C@H](C)C(O)=O)=CC=C1C1=NOC(C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=N1 VXEOCIWIHSJRHE-WAIKUNEKSA-N 0.000 description 2
• NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 2
• KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
• NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
• BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 2
• VWDZZXMOVWCUPU-UHFFFAOYSA-N 1-[4-[5-[3-methyl-4-[2-(trifluoromethyl)phenyl]phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethanamine Chemical compound C1=CC(C(N)C)=CC=C1C1=NOC(C=2C=C(C)C(=CC=2)C=2C(=CC=CC=2)C(F)(F)F)=N1 VWDZZXMOVWCUPU-UHFFFAOYSA-N 0.000 description 2
• 238000005160 1H NMR spectroscopy Methods 0.000 description 2
• XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical group COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
• PUBBEBYZUJKBAX-UHFFFAOYSA-N 2-[[2-hydroxy-1-[4-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]amino]acetic acid Chemical compound CC1=CC=CC=C1C1=CC=C(C=2ON=C(N=2)C=2C=CC(=CC=2)C(CO)NCC(O)=O)C=C1C(F)(F)F PUBBEBYZUJKBAX-UHFFFAOYSA-N 0.000 description 2
• VEJMNZSNQUQTBE-UHFFFAOYSA-N 3-(aminomethyl)-5-fluorobenzonitrile Chemical compound NCC1=CC(F)=CC(C#N)=C1 VEJMNZSNQUQTBE-UHFFFAOYSA-N 0.000 description 2
• SUIFNMFWHQFXIP-UHFFFAOYSA-N 3-(bromomethyl)-5-fluorobenzonitrile Chemical compound FC1=CC(CBr)=CC(C#N)=C1 SUIFNMFWHQFXIP-UHFFFAOYSA-N 0.000 description 2
• CVKOOKPNCVYHNY-UHFFFAOYSA-N 3-(bromomethyl)benzonitrile Chemical compound BrCC1=CC=CC(C#N)=C1 CVKOOKPNCVYHNY-UHFFFAOYSA-N 0.000 description 2
• FZFYFVXVHIGBJC-UHFFFAOYSA-N 3-[1-(methylamino)ethyl]benzonitrile Chemical compound CNC(C)C1=CC=CC(C#N)=C1 FZFYFVXVHIGBJC-UHFFFAOYSA-N 0.000 description 2
• ORMMKYADNPXZNO-UHFFFAOYSA-N 3-methyl-4-[2-(trifluoromethyl)phenyl]benzoic acid Chemical compound CC1=CC(C(O)=O)=CC=C1C1=CC=CC=C1C(F)(F)F ORMMKYADNPXZNO-UHFFFAOYSA-N 0.000 description 2
• FDGMGJFQCFFTAZ-UHFFFAOYSA-N 4-(2-methoxyacetyl)benzonitrile Chemical compound COCC(=O)C1=CC=C(C#N)C=C1 FDGMGJFQCFFTAZ-UHFFFAOYSA-N 0.000 description 2
• AYOYWYXTWZMMGA-UHFFFAOYSA-N 4-(2-methylphenyl)-3-(trifluoromethyl)benzoic acid Chemical compound CC1=CC=CC=C1C1=CC=C(C(O)=O)C=C1C(F)(F)F AYOYWYXTWZMMGA-UHFFFAOYSA-N 0.000 description 2
• ZYDCWMILCKQXDE-UHFFFAOYSA-N 4-[1-(methylamino)ethyl]benzonitrile Chemical compound CNC(C)C1=CC=C(C#N)C=C1 ZYDCWMILCKQXDE-UHFFFAOYSA-N 0.000 description 2
• LOBILSDOITWLGG-UHFFFAOYSA-N 4-[5-[3-(methoxymethyl)-4-(2-methylphenyl)phenyl]-1,2,4-oxadiazol-3-yl]benzaldehyde Chemical compound COCC1=CC(C=2ON=C(N=2)C=2C=CC(C=O)=CC=2)=CC=C1C1=CC=CC=C1C LOBILSDOITWLGG-UHFFFAOYSA-N 0.000 description 2
• 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 2
• FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 2
• 229920001817 Agar Polymers 0.000 description 2
• 201000004384 Alopecia Diseases 0.000 description 2
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
• 208000032467 Aplastic anaemia Diseases 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
• 208000009137 Behcet syndrome Diseases 0.000 description 2
• 206010004659 Biliary cirrhosis Diseases 0.000 description 2
• 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
• 238000011740 C57BL/6 mouse Methods 0.000 description 2
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
• 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
• PTOAARAWEBMLNO-KVQBGUIXSA-N Cladribine Chemical compound C1=NC=2C(N)=NC(Cl)=NC=2N1[C@H]1C[C@H](O)[C@@H](CO)O1 PTOAARAWEBMLNO-KVQBGUIXSA-N 0.000 description 2
• CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 2
• 229930105110 Cyclosporin A Natural products 0.000 description 2
• PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 description 2
• 108010036949 Cyclosporine Proteins 0.000 description 2
• 206010011831 Cytomegalovirus infection Diseases 0.000 description 2
• MTCFGRXMJLQNBG-UWTATZPHSA-N D-Serine Chemical compound OC[C@@H](N)C(O)=O MTCFGRXMJLQNBG-UWTATZPHSA-N 0.000 description 2
• 229930195711 D-Serine Natural products 0.000 description 2
• RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 2
• 206010012438 Dermatitis atopic Diseases 0.000 description 2
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 2
• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
• ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
• AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 2
• KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
• 206010060742 Endocrine ophthalmopathy Diseases 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
• 102000003688 G-Protein-Coupled Receptors Human genes 0.000 description 2
• 108090000045 G-Protein-Coupled Receptors Proteins 0.000 description 2
• 108010010803 Gelatin Proteins 0.000 description 2
• 208000009329 Graft vs Host Disease Diseases 0.000 description 2
• 206010072579 Granulomatosis with polyangiitis Diseases 0.000 description 2
• 206010019799 Hepatitis viral Diseases 0.000 description 2
• NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
• WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
• 102000003996 Interferon-beta Human genes 0.000 description 2
• 108090000467 Interferon-beta Proteins 0.000 description 2
• 102000014150 Interferons Human genes 0.000 description 2
• 108010050904 Interferons Proteins 0.000 description 2
• QNAYBMKLOCPYGJ-REOHCLBHSA-M L-alaninate Chemical compound C[C@H](N)C([O-])=O QNAYBMKLOCPYGJ-REOHCLBHSA-M 0.000 description 2
• QWCKQJZIFLGMSD-VKHMYHEASA-N L-alpha-aminobutyric acid Chemical compound CC[C@H](N)C(O)=O QWCKQJZIFLGMSD-VKHMYHEASA-N 0.000 description 2
• KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 2
• 239000004472 Lysine Substances 0.000 description 2
• KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 2
• 241000124008 Mammalia Species 0.000 description 2
• PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 2
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
• 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
• 102100023302 Myelin-oligodendrocyte glycoprotein Human genes 0.000 description 2
• 201000002481 Myositis Diseases 0.000 description 2
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
• QIAFMBKCNZACKA-UHFFFAOYSA-N N-benzoylglycine Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1 QIAFMBKCNZACKA-UHFFFAOYSA-N 0.000 description 2
• 206010028980 Neoplasm Diseases 0.000 description 2
• 206010029240 Neuritis Diseases 0.000 description 2
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
• 229930040373 Paraformaldehyde Natural products 0.000 description 2
• 108010081690 Pertussis Toxin Proteins 0.000 description 2
• 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
• 239000002202 Polyethylene glycol Substances 0.000 description 2
• 229940124158 Protease/peptidase inhibitor Drugs 0.000 description 2
• 208000007400 Relapsing-Remitting Multiple Sclerosis Diseases 0.000 description 2
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
• XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
• GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-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
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
• JQXXHWHPUNPDRT-KCFDLMDRSA-N [(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-26-[(Z)-(4-methylpiperazin-1-yl)iminomethyl]-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(29),2,4,9,19,21,25,27-octaen-13-yl] acetate Chemical compound CO[C@H]1\C=C\O[C@@]2(C)Oc3c(C2=O)c2c(O)c(\C=N/N4CCN(C)CC4)c(NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C)c(O)c2c(O)c3C JQXXHWHPUNPDRT-KCFDLMDRSA-N 0.000 description 2
• WZDFJBMTKHCLGB-UHFFFAOYSA-N [3-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]methanol Chemical compound CC1=CC=CC=C1C1=CC=C(C=2ON=C(N=2)C=2C=C(CO)C=CC=2)C=C1C(F)(F)F WZDFJBMTKHCLGB-UHFFFAOYSA-N 0.000 description 2
• BQHFECKBXAKLLH-UHFFFAOYSA-N [4-[5-[3-(methoxymethyl)-4-(2-methylphenyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]methanol Chemical compound COCC1=CC(C=2ON=C(N=2)C=2C=CC(CO)=CC=2)=CC=C1C1=CC=CC=C1C BQHFECKBXAKLLH-UHFFFAOYSA-N 0.000 description 2
• TZHVWYKAIWSQSL-UHFFFAOYSA-N [4-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]methanol Chemical compound CC1=CC=CC=C1C1=CC=C(C=2ON=C(N=2)C=2C=CC(CO)=CC=2)C=C1C(F)(F)F TZHVWYKAIWSQSL-UHFFFAOYSA-N 0.000 description 2
• 230000002378 acidificating effect Effects 0.000 description 2
• 230000004913 activation Effects 0.000 description 2
• 150000001263 acyl chlorides Chemical class 0.000 description 2
• 239000000443 aerosol Substances 0.000 description 2
• 235000010419 agar Nutrition 0.000 description 2
• 229960003767 alanine Drugs 0.000 description 2
• 230000001476 alcoholic effect Effects 0.000 description 2
• 229940072056 alginate Drugs 0.000 description 2
• 235000010443 alginic acid Nutrition 0.000 description 2
• 229920000615 alginic acid Polymers 0.000 description 2
• 229910052783 alkali metal Inorganic materials 0.000 description 2
• 150000001340 alkali metals Chemical class 0.000 description 2
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
• 150000001342 alkaline earth metals Chemical class 0.000 description 2
• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
• 125000003277 amino group Chemical group 0.000 description 2
• 125000003710 aryl alkyl group Chemical group 0.000 description 2
• 201000008937 atopic dermatitis Diseases 0.000 description 2
• 208000010668 atopic eczema Diseases 0.000 description 2
• 235000012216 bentonite Nutrition 0.000 description 2
• 239000000440 bentonite Substances 0.000 description 2
• 229910000278 bentonite Inorganic materials 0.000 description 2
• SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
• 229940077388 benzenesulfonate Drugs 0.000 description 2
• 229940050390 benzoate Drugs 0.000 description 2
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
• 229960003237 betaine Drugs 0.000 description 2
• 229920002988 biodegradable polymer Polymers 0.000 description 2
• 239000004621 biodegradable polymer Substances 0.000 description 2
• 210000004369 blood Anatomy 0.000 description 2
• 239000008280 blood Substances 0.000 description 2
• XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
• RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 2
• GTCAXTIRRLKXRU-UHFFFAOYSA-N carbamic acid methyl ester Natural products COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 2
• 150000001720 carbohydrates Chemical class 0.000 description 2
• 235000014633 carbohydrates Nutrition 0.000 description 2
• 229950005499 carbon tetrachloride Drugs 0.000 description 2
• 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
• 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
• 239000000969 carrier Substances 0.000 description 2
• 230000001413 cellular effect Effects 0.000 description 2
• 239000003638 chemical reducing agent Substances 0.000 description 2
• 230000000973 chemotherapeutic effect Effects 0.000 description 2
• 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
• VDANGULDQQJODZ-UHFFFAOYSA-N chloroprocaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1Cl VDANGULDQQJODZ-UHFFFAOYSA-N 0.000 description 2
• 229960002023 chloroprocaine Drugs 0.000 description 2
• HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
• 229960001265 ciclosporin Drugs 0.000 description 2
• 229940001468 citrate Drugs 0.000 description 2
• 229960002436 cladribine Drugs 0.000 description 2
• 238000000576 coating method Methods 0.000 description 2
• 238000001816 cooling Methods 0.000 description 2
• 230000008878 coupling Effects 0.000 description 2
• 238000010168 coupling process Methods 0.000 description 2
• 238000002425 crystallisation Methods 0.000 description 2
• 230000008025 crystallization Effects 0.000 description 2
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
• JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 description 2
• 229960004397 cyclophosphamide Drugs 0.000 description 2
• 230000034994 death Effects 0.000 description 2
• 238000010511 deprotection reaction Methods 0.000 description 2
• SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
• BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 2
• 239000003085 diluting agent Substances 0.000 description 2
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
• 108010048367 enhanced green fluorescent protein Proteins 0.000 description 2
• 210000002919 epithelial cell Anatomy 0.000 description 2
• 238000010931 ester hydrolysis Methods 0.000 description 2
• XWBDWHCCBGMXKG-UHFFFAOYSA-N ethanamine;hydron;chloride Chemical class Cl.CCN XWBDWHCCBGMXKG-UHFFFAOYSA-N 0.000 description 2
• CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 2
• 229940031098 ethanolamine Drugs 0.000 description 2
• BFRLPRPEJGYMRQ-ZWNOBZJWSA-N ethyl (2r)-2-[[(1r)-1-[4-(n'-hydroxycarbamimidoyl)phenyl]ethyl]amino]butanoate Chemical compound CCOC(=O)[C@@H](CC)N[C@H](C)C1=CC=C(C(N)=NO)C=C1 BFRLPRPEJGYMRQ-ZWNOBZJWSA-N 0.000 description 2
• 125000004494 ethyl ester group Chemical group 0.000 description 2
• LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
• 208000024711 extrinsic asthma Diseases 0.000 description 2
• 239000012894 fetal calf serum Substances 0.000 description 2
• 238000011049 filling Methods 0.000 description 2
• 235000013305 food Nutrition 0.000 description 2
• 239000000499 gel Substances 0.000 description 2
• 239000008273 gelatin Substances 0.000 description 2
• 235000011852 gelatine desserts Nutrition 0.000 description 2
• 238000007429 general method Methods 0.000 description 2
• 239000012362 glacial acetic acid Substances 0.000 description 2
• 229940050410 gluconate Drugs 0.000 description 2
• 239000010931 gold Substances 0.000 description 2
• 238000005469 granulation Methods 0.000 description 2
• 230000003179 granulation Effects 0.000 description 2
• 150000004677 hydrates Chemical class 0.000 description 2
• 229930195733 hydrocarbon Natural products 0.000 description 2
• 150000002430 hydrocarbons Chemical class 0.000 description 2
• JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 2
• WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
• 239000005457 ice water Substances 0.000 description 2
• 238000003384 imaging method Methods 0.000 description 2
• 150000002466 imines Chemical class 0.000 description 2
• 238000011065 in-situ storage Methods 0.000 description 2
• 208000015181 infectious disease Diseases 0.000 description 2
• 230000005764 inhibitory process Effects 0.000 description 2
• 229960001388 interferon-beta Drugs 0.000 description 2
• UEXQBEVWFZKHNB-UHFFFAOYSA-N intermediate 29 Natural products C1=CC(N)=CC=C1NC1=NC=CC=N1 UEXQBEVWFZKHNB-UHFFFAOYSA-N 0.000 description 2
• 238000007918 intramuscular administration Methods 0.000 description 2
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
• 239000003456 ion exchange resin Substances 0.000 description 2
• 229920003303 ion-exchange polymer Polymers 0.000 description 2
• 150000002500 ions Chemical class 0.000 description 2
• 208000023589 ischemic disease Diseases 0.000 description 2
• 206010023332 keratitis Diseases 0.000 description 2
• JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
• ROHFNLRQFUQHCH-UHFFFAOYSA-M leucinate Chemical compound CC(C)CC(N)C([O-])=O ROHFNLRQFUQHCH-UHFFFAOYSA-M 0.000 description 2
• 239000002502 liposome Substances 0.000 description 2
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
• 235000019341 magnesium sulphate Nutrition 0.000 description 2
• IUYHWZFSGMZEOG-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].C[CH-]C IUYHWZFSGMZEOG-UHFFFAOYSA-M 0.000 description 2
• 230000014759 maintenance of location Effects 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
• BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
• IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 2
• 229910052748 manganese Inorganic materials 0.000 description 2
• 239000011572 manganese Substances 0.000 description 2
• NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
• 229960003194 meglumine Drugs 0.000 description 2
• 150000002739 metals Chemical class 0.000 description 2
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
• PTTKIDGCCBNXRF-RKDXNWHRSA-N methyl (2r)-2-[[(1r)-1-[4-[(e)-n'-hydroxycarbamimidoyl]phenyl]ethyl]amino]propanoate Chemical compound COC(=O)[C@@H](C)N[C@H](C)C1=CC=C(C(N)=NO)C=C1 PTTKIDGCCBNXRF-RKDXNWHRSA-N 0.000 description 2
• QHCSUGVIKIXWAE-WOJBJXKFSA-N methyl (2r)-2-[[(1r)-1-[4-[5-[3-(methoxymethyl)-4-(2-methylphenyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]amino]propanoate Chemical compound COCC1=CC(C=2ON=C(N=2)C=2C=CC(=CC=2)[C@@H](C)N[C@H](C)C(=O)OC)=CC=C1C1=CC=CC=C1C QHCSUGVIKIXWAE-WOJBJXKFSA-N 0.000 description 2
• LUVNJSXHNGHIPF-QZTJIDSGSA-N methyl (2r)-2-[[(1r)-1-[4-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]amino]propanoate Chemical compound C1=CC([C@@H](C)N[C@H](C)C(=O)OC)=CC=C1C1=NOC(C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=N1 LUVNJSXHNGHIPF-QZTJIDSGSA-N 0.000 description 2
• BMYCXIKWTMREBD-UHFFFAOYSA-N methyl 3-(methoxymethyl)-4-(2-methylphenyl)benzoate Chemical compound COCC1=CC(C(=O)OC)=CC=C1C1=CC=CC=C1C BMYCXIKWTMREBD-UHFFFAOYSA-N 0.000 description 2
• FPYOTPGYISYHLH-UHFFFAOYSA-N methyl 4-(2-methylphenyl)-3-(trifluoromethyl)benzoate Chemical compound FC(F)(F)C1=CC(C(=O)OC)=CC=C1C1=CC=CC=C1C FPYOTPGYISYHLH-UHFFFAOYSA-N 0.000 description 2
• VLFRBILAMCQAFC-UHFFFAOYSA-N methyl 4-[2-(difluoromethyl)phenyl]-3-methylbenzoate Chemical compound CC1=CC(C(=O)OC)=CC=C1C1=CC=CC=C1C(F)F VLFRBILAMCQAFC-UHFFFAOYSA-N 0.000 description 2
• GRJDNFSKEWOMIM-UHFFFAOYSA-N methyl 4-bromo-3-(bromomethyl)benzoate Chemical compound COC(=O)C1=CC=C(Br)C(CBr)=C1 GRJDNFSKEWOMIM-UHFFFAOYSA-N 0.000 description 2
• JBRTYWDBBOLUNA-UHFFFAOYSA-N methyl 4-bromo-3-(methoxymethyl)benzoate Chemical compound COCC1=CC(C(=O)OC)=CC=C1Br JBRTYWDBBOLUNA-UHFFFAOYSA-N 0.000 description 2
• DTVRLJMSCKUEEN-UHFFFAOYSA-N methyl 4-bromo-3-(trifluoromethyl)benzoate Chemical compound COC(=O)C1=CC=C(Br)C(C(F)(F)F)=C1 DTVRLJMSCKUEEN-UHFFFAOYSA-N 0.000 description 2
• GTZTYNPAPQKIIR-UHFFFAOYSA-N methyl 4-bromo-3-methylbenzoate Chemical compound COC(=O)C1=CC=C(Br)C(C)=C1 GTZTYNPAPQKIIR-UHFFFAOYSA-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
• 238000002156 mixing Methods 0.000 description 2
• 229940113083 morpholine Drugs 0.000 description 2
• RTGDFNSFWBGLEC-SYZQJQIISA-N mycophenolate mofetil Chemical compound COC1=C(C)C=2COC(=O)C=2C(O)=C1C\C=C(/C)CCC(=O)OCCN1CCOCC1 RTGDFNSFWBGLEC-SYZQJQIISA-N 0.000 description 2
• 229960004866 mycophenolate mofetil Drugs 0.000 description 2
• 201000005962 mycosis fungoides Diseases 0.000 description 2
• NOLUPSWFOCDWBV-UHFFFAOYSA-N n'-hydroxy-3-(2-hydroxyethyl)benzenecarboximidamide Chemical compound ON=C(N)C1=CC=CC(CCO)=C1 NOLUPSWFOCDWBV-UHFFFAOYSA-N 0.000 description 2
• DKSFMGRTWCDFRB-UHFFFAOYSA-N n'-hydroxy-3-(hydroxymethyl)benzenecarboximidamide Chemical compound ON=C(N)C1=CC=CC(CO)=C1 DKSFMGRTWCDFRB-UHFFFAOYSA-N 0.000 description 2
• DSZQQTKCOGBPEM-UHFFFAOYSA-N n'-hydroxy-4-(1-hydroxyethyl)benzenecarboximidamide Chemical compound CC(O)C1=CC=C(C(N)=NO)C=C1 DSZQQTKCOGBPEM-UHFFFAOYSA-N 0.000 description 2
• ZIFIPZQBKOIQOD-UHFFFAOYSA-N n'-hydroxy-4-(2-hydroxyethyl)benzenecarboximidamide Chemical compound OCCC1=CC=C(C(=N)NO)C=C1 ZIFIPZQBKOIQOD-UHFFFAOYSA-N 0.000 description 2
• XAVQRXUCPQYHBS-UHFFFAOYSA-N n'-hydroxy-4-(hydroxymethyl)benzenecarboximidamide Chemical compound OCC1=CC=C(C(=N)NO)C=C1 XAVQRXUCPQYHBS-UHFFFAOYSA-N 0.000 description 2
• DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 2
• 229910052754 neon Inorganic materials 0.000 description 2
• GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 2
• 150000002828 nitro derivatives Chemical class 0.000 description 2
• 125000004433 nitrogen atom Chemical group N* 0.000 description 2
• LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
• 238000002414 normal-phase solid-phase extraction Methods 0.000 description 2
• 238000005935 nucleophilic addition reaction Methods 0.000 description 2
• 239000002674 ointment Substances 0.000 description 2
• 229940049964 oleate Drugs 0.000 description 2
• ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
• QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
• 229920002866 paraformaldehyde Polymers 0.000 description 2
• 230000036961 partial effect Effects 0.000 description 2
• 235000019371 penicillin G benzathine Nutrition 0.000 description 2
• 239000000137 peptide hydrolase inhibitor Substances 0.000 description 2
• UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 2
• 230000000704 physical effect Effects 0.000 description 2
• 239000002798 polar solvent Substances 0.000 description 2
• 229920000728 polyester Polymers 0.000 description 2
• 229920001223 polyethylene glycol Polymers 0.000 description 2
• 239000002861 polymer material Substances 0.000 description 2
• 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
• 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
• 230000003389 potentiating effect Effects 0.000 description 2
• 239000003755 preservative agent Substances 0.000 description 2
• 150000003141 primary amines Chemical class 0.000 description 2
• MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 2
• 229960004919 procaine Drugs 0.000 description 2
• 229940002612 prodrug Drugs 0.000 description 2
• 239000000651 prodrug Substances 0.000 description 2
• 235000019260 propionic acid Nutrition 0.000 description 2
• 238000000159 protein binding assay Methods 0.000 description 2
• 235000018102 proteins Nutrition 0.000 description 2
• 102000004169 proteins and genes Human genes 0.000 description 2
• 108090000623 proteins and genes Proteins 0.000 description 2
• ZAHRKKWIAAJSAO-UHFFFAOYSA-N rapamycin Natural products COCC(O)C(=C/C(C)C(=O)CC(OC(=O)C1CCCCN1C(=O)C(=O)C2(O)OC(CC(OC)C(=CC=CC=CC(C)CC(C)C(=O)C)C)CCC2C)C(C)CC3CCC(O)C(C3)OC)C ZAHRKKWIAAJSAO-UHFFFAOYSA-N 0.000 description 2
• 230000009467 reduction Effects 0.000 description 2
• 238000006722 reduction reaction Methods 0.000 description 2
• 239000011347 resin Substances 0.000 description 2
• 229920005989 resin Polymers 0.000 description 2
• 150000003335 secondary amines Chemical class 0.000 description 2
• 239000000741 silica gel Substances 0.000 description 2
• 229910002027 silica gel Inorganic materials 0.000 description 2
• WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 2
• 239000004299 sodium benzoate Substances 0.000 description 2
• 235000010234 sodium benzoate Nutrition 0.000 description 2
• 239000012312 sodium hydride Substances 0.000 description 2
• 229910000104 sodium hydride Inorganic materials 0.000 description 2
• 239000007790 solid phase Substances 0.000 description 2
• WWUZIQQURGPMPG-KRWOKUGFSA-N sphingosine Chemical compound CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)CO WWUZIQQURGPMPG-KRWOKUGFSA-N 0.000 description 2
• 239000007921 spray Substances 0.000 description 2
• UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
• 238000007920 subcutaneous administration Methods 0.000 description 2
• 238000006467 substitution reaction Methods 0.000 description 2
• KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
• 150000008163 sugars Chemical class 0.000 description 2
• 150000003460 sulfonic acids Chemical class 0.000 description 2
• 150000003462 sulfoxides Chemical class 0.000 description 2
• 229960001967 tacrolimus Drugs 0.000 description 2
• 239000000454 talc Substances 0.000 description 2
• 229910052623 talc Inorganic materials 0.000 description 2
• 235000012222 talc Nutrition 0.000 description 2
• 229940095064 tartrate Drugs 0.000 description 2
• VGTDFFIUFFPSOV-YNODCEANSA-N tert-butyl (2r)-2-[[1-(4-cyanophenyl)-2-hydroxyethyl]amino]propanoate Chemical compound CC(C)(C)OC(=O)[C@@H](C)NC(CO)C1=CC=C(C#N)C=C1 VGTDFFIUFFPSOV-YNODCEANSA-N 0.000 description 2
• GKOWZBHRTWQJDX-HNNXBMFYSA-N tert-butyl (2s)-2-[[2-fluoro-4-(n'-hydroxycarbamimidoyl)phenyl]methyl-methylamino]-3-methylbutanoate Chemical compound CC(C)(C)OC(=O)[C@H](C(C)C)N(C)CC1=CC=C(C(N)=NO)C=C1F GKOWZBHRTWQJDX-HNNXBMFYSA-N 0.000 description 2
• GDXSAJTVDCURMS-NRFANRHFSA-N tert-butyl (2s)-2-[[2-fluoro-4-[5-[3-(methoxymethyl)-4-(2-methylphenyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl-methylamino]propanoate Chemical compound COCC1=CC(C=2ON=C(N=2)C=2C=C(F)C(CN(C)[C@@H](C)C(=O)OC(C)(C)C)=CC=2)=CC=C1C1=CC=CC=C1C GDXSAJTVDCURMS-NRFANRHFSA-N 0.000 description 2
• YCQRPYLTPOPGMV-LJAQVGFWSA-N tert-butyl (2s)-2-[[2-fluoro-4-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl-methylamino]-3-[(2-methylpropan-2-yl)oxy]propanoate Chemical compound C1=C(F)C(CN(C)[C@@H](COC(C)(C)C)C(=O)OC(C)(C)C)=CC=C1C1=NOC(C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=N1 YCQRPYLTPOPGMV-LJAQVGFWSA-N 0.000 description 2
• ZLUSQYGWUMEZEC-NDEPHWFRSA-N tert-butyl (2s)-3-methyl-2-[2-[4-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethylamino]butanoate Chemical compound C1=CC(CCN[C@@H](C(C)C)C(=O)OC(C)(C)C)=CC=C1C1=NOC(C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=N1 ZLUSQYGWUMEZEC-NDEPHWFRSA-N 0.000 description 2
• XPROUDBFRJFPDJ-UHFFFAOYSA-N tert-butyl 2-(benzylamino)-2-methylpropanoate Chemical compound CC(C)(C)OC(=O)C(C)(C)NCC1=CC=CC=C1 XPROUDBFRJFPDJ-UHFFFAOYSA-N 0.000 description 2
• LZNIDSDQLUAYNN-UHFFFAOYSA-N tert-butyl 2-[(3-cyanophenyl)methyl-methylamino]acetate Chemical compound CC(C)(C)OC(=O)CN(C)CC1=CC=CC(C#N)=C1 LZNIDSDQLUAYNN-UHFFFAOYSA-N 0.000 description 2
• AUTQYEHDWDRCET-UHFFFAOYSA-N tert-butyl 2-[(4-cyano-2-fluorophenyl)methyl-methylamino]-3-[(2-methylpropan-2-yl)oxy]propanoate Chemical compound CC(C)(C)OCC(C(=O)OC(C)(C)C)N(C)CC1=CC=C(C#N)C=C1F AUTQYEHDWDRCET-UHFFFAOYSA-N 0.000 description 2
• IQDMTAVFQGXHBE-UHFFFAOYSA-N tert-butyl 2-[(4-cyano-2-fluorophenyl)methylamino]-3-[(2-methylpropan-2-yl)oxy]propanoate Chemical compound CC(C)(C)OCC(C(=O)OC(C)(C)C)NCC1=CC=C(C#N)C=C1F IQDMTAVFQGXHBE-UHFFFAOYSA-N 0.000 description 2
• WNUQAKWJHFOTAN-UHFFFAOYSA-N tert-butyl 2-[1-(3-cyanophenyl)ethylamino]acetate Chemical compound CC(C)(C)OC(=O)CNC(C)C1=CC=CC(C#N)=C1 WNUQAKWJHFOTAN-UHFFFAOYSA-N 0.000 description 2
• CAYDXGDDOJYSAP-UHFFFAOYSA-N tert-butyl 2-[1-[3-(n'-hydroxycarbamimidoyl)phenyl]ethylamino]acetate Chemical compound CC(C)(C)OC(=O)CNC(C)C1=CC=CC(C(N)=NO)=C1 CAYDXGDDOJYSAP-UHFFFAOYSA-N 0.000 description 2
• ACZCUMNKRUGMDJ-UHFFFAOYSA-N tert-butyl 2-[1-[4-(n'-hydroxycarbamimidoyl)phenyl]ethyl-methylamino]acetate Chemical compound CC(C)(C)OC(=O)CN(C)C(C)C1=CC=C(C(N)=NO)C=C1 ACZCUMNKRUGMDJ-UHFFFAOYSA-N 0.000 description 2
• NOIVRGSWZAPXET-UHFFFAOYSA-N tert-butyl 2-[1-[4-[(e)-n'-hydroxycarbamimidoyl]phenyl]ethylamino]acetate Chemical compound CC(C)(C)OC(=O)CNC(C)C1=CC=C(C(N)=NO)C=C1 NOIVRGSWZAPXET-UHFFFAOYSA-N 0.000 description 2
• VJDIQWCOTKQWAX-UHFFFAOYSA-N tert-butyl 2-[1-[4-[5-[3-(methoxymethyl)-4-(2-methylphenyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl-methylamino]acetate Chemical compound COCC1=CC(C=2ON=C(N=2)C=2C=CC(=CC=2)C(C)N(C)CC(=O)OC(C)(C)C)=CC=C1C1=CC=CC=C1C VJDIQWCOTKQWAX-UHFFFAOYSA-N 0.000 description 2
• NOIVRGSWZAPXET-SNVBAGLBSA-N tert-butyl 2-[[(1r)-1-[4-[(z)-n'-hydroxycarbamimidoyl]phenyl]ethyl]amino]acetate Chemical compound CC(C)(C)OC(=O)CN[C@H](C)C1=CC=C(C(=N)NO)C=C1 NOIVRGSWZAPXET-SNVBAGLBSA-N 0.000 description 2
• DGAIYWJSULEHFU-LJQANCHMSA-N tert-butyl 2-[[(1r)-1-[4-[5-[4-[2-(difluoromethyl)phenyl]-3-methylphenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]amino]acetate Chemical compound C1=CC([C@H](NCC(=O)OC(C)(C)C)C)=CC=C1C1=NOC(C=2C=C(C)C(=CC=2)C=2C(=CC=CC=2)C(F)F)=N1 DGAIYWJSULEHFU-LJQANCHMSA-N 0.000 description 2
• ACZCUMNKRUGMDJ-NSHDSACASA-N tert-butyl 2-[[(1s)-1-[4-[(e)-n'-hydroxycarbamimidoyl]phenyl]ethyl]-methylamino]acetate Chemical compound CC(C)(C)OC(=O)CN(C)[C@@H](C)C1=CC=C(C(N)=NO)C=C1 ACZCUMNKRUGMDJ-NSHDSACASA-N 0.000 description 2
• NOIVRGSWZAPXET-JTQLQIEISA-N tert-butyl 2-[[(1s)-1-[4-[(z)-n'-hydroxycarbamimidoyl]phenyl]ethyl]amino]acetate Chemical compound CC(C)(C)OC(=O)CN[C@@H](C)C1=CC=C(C(=N)NO)C=C1 NOIVRGSWZAPXET-JTQLQIEISA-N 0.000 description 2
• SEMQOVVLEJTZQT-UHFFFAOYSA-N tert-butyl 2-[[1-(4-cyanophenyl)-2-hydroxyethyl]amino]acetate Chemical compound CC(C)(C)OC(=O)CNC(CO)C1=CC=C(C#N)C=C1 SEMQOVVLEJTZQT-UHFFFAOYSA-N 0.000 description 2
• VFFXQJKUTPUMLT-UHFFFAOYSA-N tert-butyl 2-[[1-[4-(n'-hydroxycarbamimidoyl)phenyl]-2-methoxyethyl]-methylamino]acetate Chemical compound CC(C)(C)OC(=O)CN(C)C(COC)C1=CC=C(C(N)=NO)C=C1 VFFXQJKUTPUMLT-UHFFFAOYSA-N 0.000 description 2
• NIFFVFDNRWEWEC-UHFFFAOYSA-N tert-butyl 2-[[2-fluoro-4-[(e)-n'-hydroxycarbamimidoyl]phenyl]methyl-methylamino]butanoate Chemical compound CC(C)(C)OC(=O)C(CC)N(C)CC1=CC=C(C(N)=NO)C=C1F NIFFVFDNRWEWEC-UHFFFAOYSA-N 0.000 description 2
• YAVOOYFWSBKOCK-UHFFFAOYSA-N tert-butyl 2-[[2-fluoro-4-[5-[3-(methoxymethyl)-4-(2-methylphenyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl-methylamino]-2-methylpropanoate Chemical compound COCC1=CC(C=2ON=C(N=2)C=2C=C(F)C(CN(C)C(C)(C)C(=O)OC(C)(C)C)=CC=2)=CC=C1C1=CC=CC=C1C YAVOOYFWSBKOCK-UHFFFAOYSA-N 0.000 description 2
• MLLOMIQNALXXKE-UHFFFAOYSA-N tert-butyl 2-[[2-fluoro-4-[5-[3-(methoxymethyl)-4-(2-methylphenyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]methylamino]-2-methylpropanoate Chemical compound COCC1=CC(C=2ON=C(N=2)C=2C=C(F)C(CNC(C)(C)C(=O)OC(C)(C)C)=CC=2)=CC=C1C1=CC=CC=C1C MLLOMIQNALXXKE-UHFFFAOYSA-N 0.000 description 2
• NACRBOPNXMXCEP-UHFFFAOYSA-N tert-butyl 2-[[2-fluoro-4-[5-[3-methyl-4-[2-(trifluoromethyl)phenyl]phenyl]-1,2,4-oxadiazol-3-yl]phenyl]methylamino]-2-methylpropanoate Chemical compound CC1=CC(C=2ON=C(N=2)C=2C=C(F)C(CNC(C)(C)C(=O)OC(C)(C)C)=CC=2)=CC=C1C1=CC=CC=C1C(F)(F)F NACRBOPNXMXCEP-UHFFFAOYSA-N 0.000 description 2
• JAXBPZJELIGCLU-UHFFFAOYSA-N tert-butyl 2-[[2-fluoro-4-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl-methylamino]-2-methylpropanoate Chemical compound C1=C(F)C(CN(C)C(C)(C)C(=O)OC(C)(C)C)=CC=C1C1=NOC(C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=N1 JAXBPZJELIGCLU-UHFFFAOYSA-N 0.000 description 2
• XDCZILRQVHFPEA-UHFFFAOYSA-N tert-butyl 2-[[2-fluoro-4-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]methylamino]-2-methylpropanoate Chemical compound CC1=CC=CC=C1C1=CC=C(C=2ON=C(N=2)C=2C=C(F)C(CNC(C)(C)C(=O)OC(C)(C)C)=CC=2)C=C1C(F)(F)F XDCZILRQVHFPEA-UHFFFAOYSA-N 0.000 description 2
• USPWGRBYHUFUDC-UHFFFAOYSA-N tert-butyl 2-[[2-fluoro-4-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]methylamino]butanoate Chemical compound C1=C(F)C(CNC(CC)C(=O)OC(C)(C)C)=CC=C1C1=NOC(C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=N1 USPWGRBYHUFUDC-UHFFFAOYSA-N 0.000 description 2
• HVRFJUJQSCGYFO-UHFFFAOYSA-N tert-butyl 2-[methyl-[1-[3-[5-[3-methyl-4-[2-(trifluoromethyl)phenyl]phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]amino]acetate Chemical compound CC(C)(C)OC(=O)CN(C)C(C)C1=CC=CC(C=2N=C(ON=2)C=2C=C(C)C(=CC=2)C=2C(=CC=CC=2)C(F)(F)F)=C1 HVRFJUJQSCGYFO-UHFFFAOYSA-N 0.000 description 2
• UZHNWSLHLJLEAZ-UHFFFAOYSA-N tert-butyl 2-aminobutanoate Chemical compound CCC(N)C(=O)OC(C)(C)C UZHNWSLHLJLEAZ-UHFFFAOYSA-N 0.000 description 2
• RIUJWUWLGXBICR-UHFFFAOYSA-N tert-butyl 2-bromobutanoate Chemical compound CCC(Br)C(=O)OC(C)(C)C RIUJWUWLGXBICR-UHFFFAOYSA-N 0.000 description 2
• SYCYTDVODOGBBU-SNVBAGLBSA-N tert-butyl n-[(1r)-1-(4-cyanophenyl)ethyl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@H](C)C1=CC=C(C#N)C=C1 SYCYTDVODOGBBU-SNVBAGLBSA-N 0.000 description 2
• UPJGKJGWLLBCPQ-UHFFFAOYSA-N tert-butyl n-[2-(3-cyanophenyl)ethyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCC1=CC=CC(C#N)=C1 UPJGKJGWLLBCPQ-UHFFFAOYSA-N 0.000 description 2
• BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 2
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
• YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 description 2
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
• UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 2
• GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
• 229960004418 trolamine Drugs 0.000 description 2
• 229910052721 tungsten Inorganic materials 0.000 description 2
• 238000000825 ultraviolet detection Methods 0.000 description 2
• 239000002691 unilamellar liposome Substances 0.000 description 2
• 210000001364 upper extremity Anatomy 0.000 description 2
• 230000004218 vascular function Effects 0.000 description 2
• 239000003981 vehicle Substances 0.000 description 2
• 239000000230 xanthan gum Substances 0.000 description 2
• 235000010493 xanthan gum Nutrition 0.000 description 2
• 229920001285 xanthan gum Polymers 0.000 description 2
• 229940082509 xanthan gum Drugs 0.000 description 2
• 239000008096 xylene Substances 0.000 description 2
• LSPHULWDVZXLIL-UHFFFAOYSA-N (+/-)-Camphoric acid Chemical compound CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 description 1
• JGQYBOLWNKUMPB-OAHLLOKOSA-N (1r)-1-[4-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethanamine Chemical compound C1=CC([C@H](N)C)=CC=C1C1=NOC(C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=N1 JGQYBOLWNKUMPB-OAHLLOKOSA-N 0.000 description 1
• QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
• AQHRZSDIYFOKKH-RTBURBONSA-N (2r)-2-[[(1r)-1-[4-[5-[3-(methoxymethyl)-4-(2-methylphenyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]amino]propanoic acid Chemical compound COCC1=CC(C=2ON=C(N=2)C=2C=CC(=CC=2)[C@@H](C)N[C@H](C)C(O)=O)=CC=C1C1=CC=CC=C1C AQHRZSDIYFOKKH-RTBURBONSA-N 0.000 description 1
• DBSAGOILNWAUKS-MZNJEOGPSA-N (2r)-2-[[(1r)-1-[4-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]amino]butanoic acid Chemical compound C1=CC([C@@H](C)N[C@H](CC)C(O)=O)=CC=C1C1=NOC(C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=N1 DBSAGOILNWAUKS-MZNJEOGPSA-N 0.000 description 1
• VXEOCIWIHSJRHE-MWTRTKDXSA-N (2r)-2-[[(1r)-2-hydroxy-1-[4-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]amino]propanoic acid Chemical compound C1=CC([C@H](CO)N[C@H](C)C(O)=O)=CC=C1C1=NOC(C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=N1 VXEOCIWIHSJRHE-MWTRTKDXSA-N 0.000 description 1
• AQHRZSDIYFOKKH-RBUKOAKNSA-N (2r)-2-[[(1s)-1-[4-[5-[3-(methoxymethyl)-4-(2-methylphenyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]amino]propanoic acid Chemical compound COCC1=CC(C=2ON=C(N=2)C=2C=CC(=CC=2)[C@H](C)N[C@H](C)C(O)=O)=CC=C1C1=CC=CC=C1C AQHRZSDIYFOKKH-RBUKOAKNSA-N 0.000 description 1
• FRPFJDYPZKUMCV-XMMPIXPASA-N (2r)-2-[ethyl-[[3-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]amino]-3-hydroxypropanoic acid Chemical compound OC[C@H](C(O)=O)N(CC)CC1=CC=CC(C=2N=C(ON=2)C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=C1 FRPFJDYPZKUMCV-XMMPIXPASA-N 0.000 description 1
• NNGOEKYKVFUOHQ-GOSISDBHSA-N (2r)-2-[ethyl-[[4-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]amino]propanoic acid Chemical compound C1=CC(CN(CC)[C@H](C)C(O)=O)=CC=C1C1=NOC(C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=N1 NNGOEKYKVFUOHQ-GOSISDBHSA-N 0.000 description 1
• DNISEZBAYYIQFB-PHDIDXHHSA-N (2r,3r)-2,3-diacetyloxybutanedioic acid Chemical compound CC(=O)O[C@@H](C(O)=O)[C@H](C(O)=O)OC(C)=O DNISEZBAYYIQFB-PHDIDXHHSA-N 0.000 description 1
• JUSWZYFYLXTMLJ-JTQLQIEISA-N (2s)-1-(benzenesulfonyl)pyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@@H]1CCCN1S(=O)(=O)C1=CC=CC=C1 JUSWZYFYLXTMLJ-JTQLQIEISA-N 0.000 description 1
• RQYKQWFHJOBBAO-JTQLQIEISA-N (2s)-1-benzoylpyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@@H]1CCCN1C(=O)C1=CC=CC=C1 RQYKQWFHJOBBAO-JTQLQIEISA-N 0.000 description 1
• ZSMUPCRXHUDCKK-ANYOKISRSA-N (2s)-2-[1-[4-[5-[3-(methoxymethyl)-4-(2-methylphenyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl-methylamino]propanoic acid Chemical compound COCC1=CC(C=2ON=C(N=2)C=2C=CC(=CC=2)C(C)N(C)[C@@H](C)C(O)=O)=CC=C1C1=CC=CC=C1C ZSMUPCRXHUDCKK-ANYOKISRSA-N 0.000 description 1
• LXUUXXCBMHIPDA-KRWDZBQOSA-N (2s)-2-[2-[3-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethylamino]propanoic acid Chemical compound OC(=O)[C@H](C)NCCC1=CC=CC(C=2N=C(ON=2)C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=C1 LXUUXXCBMHIPDA-KRWDZBQOSA-N 0.000 description 1
• DYZJTXQWJDJFJX-QHCPKHFHSA-N (2s)-2-[[2-fluoro-4-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl-methylamino]-3-hydroxypropanoic acid Chemical compound C1=C(F)C(CN(C)[C@@H](CO)C(O)=O)=CC=C1C1=NOC(C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=N1 DYZJTXQWJDJFJX-QHCPKHFHSA-N 0.000 description 1
• MOKBBBVMFRMYBZ-VWLOTQADSA-N (2s)-2-[[2-fluoro-4-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl-methylamino]-3-methylbutanoic acid Chemical compound C1=C(F)C(CN(C)[C@@H](C(C)C)C(O)=O)=CC=C1C1=NOC(C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=N1 MOKBBBVMFRMYBZ-VWLOTQADSA-N 0.000 description 1
• DFFTUUPJPLRTOW-INIZCTEOSA-N (2s)-2-[[2-fluoro-4-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl-methylamino]propanoic acid Chemical compound C1=C(F)C(CN(C)[C@@H](C)C(O)=O)=CC=C1C1=NOC(C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=N1 DFFTUUPJPLRTOW-INIZCTEOSA-N 0.000 description 1
• QVBHIUXQSCGOHQ-DEOSSOPVSA-N (2s)-2-[[2-fluoro-4-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]methylamino]-3-methylbutanoic acid Chemical compound C1=C(F)C(CN[C@@H](C(C)C)C(O)=O)=CC=C1C1=NOC(C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=N1 QVBHIUXQSCGOHQ-DEOSSOPVSA-N 0.000 description 1
• PABVTXXPAWQPPO-VWLOTQADSA-N (2s)-2-[[3-fluoro-5-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]methylamino]-4-methylpentanoic acid Chemical compound CC(C)C[C@@H](C(O)=O)NCC1=CC(F)=CC(C=2N=C(ON=2)C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=C1 PABVTXXPAWQPPO-VWLOTQADSA-N 0.000 description 1
• BITWDJOPJWSEHI-QHCPKHFHSA-N (2s)-2-[[4-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]methylamino]butanoic acid Chemical compound C1=CC(CN[C@@H](CC)C(O)=O)=CC=C1C1=NOC(C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=N1 BITWDJOPJWSEHI-QHCPKHFHSA-N 0.000 description 1
• NNGOEKYKVFUOHQ-SFHVURJKSA-N (2s)-2-[ethyl-[[4-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]amino]propanoic acid Chemical compound C1=CC(CN(CC)[C@@H](C)C(O)=O)=CC=C1C1=NOC(C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=N1 NNGOEKYKVFUOHQ-SFHVURJKSA-N 0.000 description 1
• WVTUFPJMPXZGHD-ZVAWYAOSSA-N (2s)-2-[methyl-[1-[3-[5-[3-methyl-4-[2-(trifluoromethyl)phenyl]phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]amino]propanoic acid Chemical compound OC(=O)[C@H](C)N(C)C(C)C1=CC=CC(C=2N=C(ON=2)C=2C=C(C)C(=CC=2)C=2C(=CC=CC=2)C(F)(F)F)=C1 WVTUFPJMPXZGHD-ZVAWYAOSSA-N 0.000 description 1
• BXLWWUZZHOFSJK-ZVAWYAOSSA-N (2s)-2-[methyl-[1-[3-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]amino]propanoic acid Chemical compound OC(=O)[C@H](C)N(C)C(C)C1=CC=CC(C=2N=C(ON=2)C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=C1 BXLWWUZZHOFSJK-ZVAWYAOSSA-N 0.000 description 1
• FJJYAQPIWMCBHH-ZVAWYAOSSA-N (2s)-2-[methyl-[1-[4-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]amino]propanoic acid Chemical compound C1=CC(C(C)N(C)[C@@H](C)C(O)=O)=CC=C1C1=NOC(C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=N1 FJJYAQPIWMCBHH-ZVAWYAOSSA-N 0.000 description 1
• MSTBMOXVMLTRGM-VWLOTQADSA-N (2s)-3-methyl-2-[2-[4-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethylamino]butanoic acid Chemical compound C1=CC(CCN[C@@H](C(C)C)C(O)=O)=CC=C1C1=NOC(C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=N1 MSTBMOXVMLTRGM-VWLOTQADSA-N 0.000 description 1
• ZMKGDQSIRSGUDJ-VSROPUKISA-N (3s,6s,9s,12r,15s,18s,21s,24s,30s,33s)-33-[(e,1r,2r)-1-hydroxy-2-methylhex-4-enyl]-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18,24-tetrakis(2-methylpropyl)-3,21-di(propan-2-yl)-30-propyl-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacontane-2,5,8,11,14,1 Chemical compound CCC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O ZMKGDQSIRSGUDJ-VSROPUKISA-N 0.000 description 1
• CZJXBZPJABCCRQ-BULBTXNYSA-N (8s,9r,10s,11s,13s,14s,17r)-9,11-dichloro-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one Chemical compound O=C1C=C[C@]2(C)[C@@]3(Cl)[C@@H](Cl)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 CZJXBZPJABCCRQ-BULBTXNYSA-N 0.000 description 1
• BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
• 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 1
• GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 1
• YHRHVIQHPYUKDO-UHFFFAOYSA-N 1-[3-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethanol Chemical compound CC(O)C1=CC=CC(C=2N=C(ON=2)C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=C1 YHRHVIQHPYUKDO-UHFFFAOYSA-N 0.000 description 1
• JGQYBOLWNKUMPB-UHFFFAOYSA-N 1-[4-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethanamine Chemical compound C1=CC(C(N)C)=CC=C1C1=NOC(C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=N1 JGQYBOLWNKUMPB-UHFFFAOYSA-N 0.000 description 1
• IMQYMMQGSJEFSC-UHFFFAOYSA-N 1-[[4-[5-[3-(methoxymethyl)-4-(2-methylphenyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl-methylamino]cyclopentane-1-carboxylic acid Chemical compound COCC1=CC(C=2ON=C(N=2)C=2C=CC(CN(C)C3(CCCC3)C(O)=O)=CC=2)=CC=C1C1=CC=CC=C1C IMQYMMQGSJEFSC-UHFFFAOYSA-N 0.000 description 1
• NILQLFBWTXNUOE-UHFFFAOYSA-N 1-aminocyclopentanecarboxylic acid Chemical compound OC(=O)C1(N)CCCC1 NILQLFBWTXNUOE-UHFFFAOYSA-N 0.000 description 1
• LLAPDLPYIYKTGQ-UHFFFAOYSA-N 1-aminoethyl Chemical group C[CH]N LLAPDLPYIYKTGQ-UHFFFAOYSA-N 0.000 description 1
• RMYPQIOCZSWSDG-UHFFFAOYSA-N 1-bromo-2-(difluoromethyl)benzene Chemical compound FC(F)C1=CC=CC=C1Br RMYPQIOCZSWSDG-UHFFFAOYSA-N 0.000 description 1
• AESJJUATRJNEOJ-UHFFFAOYSA-N 1-carboxy-n-methyl-n-[[4-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopentan-1-amine oxide Chemical compound CC1=CC=CC=C1C1=CC=C(C=2ON=C(N=2)C=2C=CC(C[N+](C)([O-])C3(CCCC3)C(O)=O)=CC=2)C=C1C(F)(F)F AESJJUATRJNEOJ-UHFFFAOYSA-N 0.000 description 1
• VUQPJRPDRDVQMN-UHFFFAOYSA-N 1-chlorooctadecane Chemical compound CCCCCCCCCCCCCCCCCCCl VUQPJRPDRDVQMN-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
• 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
• UEJJHQNACJXSKW-UHFFFAOYSA-N 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C1CCC(=O)NC1=O UEJJHQNACJXSKW-UHFFFAOYSA-N 0.000 description 1
• OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
• UZYQSNQJLWTICD-UHFFFAOYSA-N 2-(n-benzoylanilino)-2,2-dinitroacetic acid Chemical compound C=1C=CC=CC=1N(C(C(=O)O)([N+]([O-])=O)[N+]([O-])=O)C(=O)C1=CC=CC=C1 UZYQSNQJLWTICD-UHFFFAOYSA-N 0.000 description 1
• FUOOLUPWFVMBKG-UHFFFAOYSA-N 2-Aminoisobutyric acid Chemical compound CC(C)(N)C(O)=O FUOOLUPWFVMBKG-UHFFFAOYSA-N 0.000 description 1
• BWRYXIFMVRPJSY-UHFFFAOYSA-N 2-[1-[3-[5-[3-methyl-4-[2-(trifluoromethyl)phenyl]phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethylamino]acetic acid Chemical compound OC(=O)CNC(C)C1=CC=CC(C=2N=C(ON=2)C=2C=C(C)C(=CC=2)C=2C(=CC=CC=2)C(F)(F)F)=C1 BWRYXIFMVRPJSY-UHFFFAOYSA-N 0.000 description 1
• DFCWUUWAPPDCQU-UHFFFAOYSA-N 2-[1-[3-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethylamino]acetic acid Chemical compound OC(=O)CNC(C)C1=CC=CC(C=2N=C(ON=2)C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=C1 DFCWUUWAPPDCQU-UHFFFAOYSA-N 0.000 description 1
• JAZOVBUNFUGASA-UHFFFAOYSA-N 2-[1-[4-[5-[3-(methoxymethyl)-4-(2-methylphenyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl-methylamino]acetic acid Chemical compound COCC1=CC(C=2ON=C(N=2)C=2C=CC(=CC=2)C(C)N(C)CC(O)=O)=CC=C1C1=CC=CC=C1C JAZOVBUNFUGASA-UHFFFAOYSA-N 0.000 description 1
• XAZOTSAHYKCDDA-UHFFFAOYSA-N 2-[1-[4-[5-[3-methyl-4-[2-(trifluoromethyl)phenyl]phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethylamino]acetic acid Chemical compound C1=CC(C(NCC(O)=O)C)=CC=C1C1=NOC(C=2C=C(C)C(=CC=2)C=2C(=CC=CC=2)C(F)(F)F)=N1 XAZOTSAHYKCDDA-UHFFFAOYSA-N 0.000 description 1
• LEINXTMVMOTJLN-UHFFFAOYSA-N 2-[1-[4-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethylamino]acetic acid Chemical compound C1=CC(C(NCC(O)=O)C)=CC=C1C1=NOC(C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=N1 LEINXTMVMOTJLN-UHFFFAOYSA-N 0.000 description 1
• JAZOVBUNFUGASA-LJQANCHMSA-N 2-[[(1r)-1-[4-[5-[3-(methoxymethyl)-4-(2-methylphenyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]-methylamino]acetic acid Chemical compound COCC1=CC(C=2ON=C(N=2)C=2C=CC(=CC=2)[C@@H](C)N(C)CC(O)=O)=CC=C1C1=CC=CC=C1C JAZOVBUNFUGASA-LJQANCHMSA-N 0.000 description 1
• ZMMUNCDLDSJZJU-GOSISDBHSA-N 2-[[(1r)-1-[4-[5-[3-(methoxymethyl)-4-(2-methylphenyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]amino]acetic acid Chemical compound COCC1=CC(C=2ON=C(N=2)C=2C=CC(=CC=2)[C@@H](C)NCC(O)=O)=CC=C1C1=CC=CC=C1C ZMMUNCDLDSJZJU-GOSISDBHSA-N 0.000 description 1
• XAZOTSAHYKCDDA-MRXNPFEDSA-N 2-[[(1r)-1-[4-[5-[3-methyl-4-[2-(trifluoromethyl)phenyl]phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]amino]acetic acid Chemical compound C1=CC([C@H](NCC(O)=O)C)=CC=C1C1=NOC(C=2C=C(C)C(=CC=2)C=2C(=CC=CC=2)C(F)(F)F)=N1 XAZOTSAHYKCDDA-MRXNPFEDSA-N 0.000 description 1
• LEINXTMVMOTJLN-MRXNPFEDSA-N 2-[[(1r)-1-[4-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]amino]acetic acid Chemical compound C1=CC([C@H](NCC(O)=O)C)=CC=C1C1=NOC(C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=N1 LEINXTMVMOTJLN-MRXNPFEDSA-N 0.000 description 1
• NFTCMBRSFLSKSE-MRXNPFEDSA-N 2-[[(1r)-1-[4-[5-[4-[2-(difluoromethyl)phenyl]-3-methylphenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]amino]acetic acid Chemical compound C1=CC([C@H](NCC(O)=O)C)=CC=C1C1=NOC(C=2C=C(C)C(=CC=2)C=2C(=CC=CC=2)C(F)F)=N1 NFTCMBRSFLSKSE-MRXNPFEDSA-N 0.000 description 1
• JAZOVBUNFUGASA-IBGZPJMESA-N 2-[[(1s)-1-[4-[5-[3-(methoxymethyl)-4-(2-methylphenyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]-methylamino]acetic acid Chemical compound COCC1=CC(C=2ON=C(N=2)C=2C=CC(=CC=2)[C@H](C)N(C)CC(O)=O)=CC=C1C1=CC=CC=C1C JAZOVBUNFUGASA-IBGZPJMESA-N 0.000 description 1
• ZMMUNCDLDSJZJU-SFHVURJKSA-N 2-[[(1s)-1-[4-[5-[3-(methoxymethyl)-4-(2-methylphenyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]amino]acetic acid Chemical compound COCC1=CC(C=2ON=C(N=2)C=2C=CC(=CC=2)[C@H](C)NCC(O)=O)=CC=C1C1=CC=CC=C1C ZMMUNCDLDSJZJU-SFHVURJKSA-N 0.000 description 1
• ADEFKSGWKUVQBO-UHFFFAOYSA-N 2-[[2-fluoro-4-[5-[3-(methoxymethyl)-4-(2-methylphenyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl-methylamino]-2-methylpropanoic acid Chemical compound COCC1=CC(C=2ON=C(N=2)C=2C=C(F)C(CN(C)C(C)(C)C(O)=O)=CC=2)=CC=C1C1=CC=CC=C1C ADEFKSGWKUVQBO-UHFFFAOYSA-N 0.000 description 1
• WUCZGRZVXBRPDB-UHFFFAOYSA-N 2-[[2-fluoro-4-[5-[3-(methoxymethyl)-4-(2-methylphenyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]methylamino]-2-methylpropanoic acid Chemical compound COCC1=CC(C=2ON=C(N=2)C=2C=C(F)C(CNC(C)(C)C(O)=O)=CC=2)=CC=C1C1=CC=CC=C1C WUCZGRZVXBRPDB-UHFFFAOYSA-N 0.000 description 1
• XCZBTWQEBPAMSS-UHFFFAOYSA-N 2-[[2-fluoro-4-[5-[3-methyl-4-[2-(trifluoromethyl)phenyl]phenyl]-1,2,4-oxadiazol-3-yl]phenyl]methylamino]-2-methylpropanoic acid Chemical compound CC1=CC(C=2ON=C(N=2)C=2C=C(F)C(CNC(C)(C)C(O)=O)=CC=2)=CC=C1C1=CC=CC=C1C(F)(F)F XCZBTWQEBPAMSS-UHFFFAOYSA-N 0.000 description 1
• HRJRIQQOOWVHAH-UHFFFAOYSA-N 2-[[2-fluoro-4-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl-methylamino]-2-methylpropanoic acid Chemical compound C1=C(F)C(CN(C)C(C)(C)C(O)=O)=CC=C1C1=NOC(C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=N1 HRJRIQQOOWVHAH-UHFFFAOYSA-N 0.000 description 1
• RHRYVABABYPEGG-UHFFFAOYSA-N 2-[[2-fluoro-4-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]methylamino]-2-methylpropanoic acid Chemical compound CC1=CC=CC=C1C1=CC=C(C=2ON=C(N=2)C=2C=C(F)C(CNC(C)(C)C(O)=O)=CC=2)C=C1C(F)(F)F RHRYVABABYPEGG-UHFFFAOYSA-N 0.000 description 1
• XHCRLRZWYZOSRG-UHFFFAOYSA-N 2-[[2-fluoro-4-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]methylamino]butanoic acid Chemical compound C1=C(F)C(CNC(CC)C(O)=O)=CC=C1C1=NOC(C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=N1 XHCRLRZWYZOSRG-UHFFFAOYSA-N 0.000 description 1
• LQXFNPWWDRBZKT-UHFFFAOYSA-N 2-[[2-methoxy-1-[4-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]-methylamino]acetic acid Chemical compound C1=CC(C(N(C)CC(O)=O)COC)=CC=C1C1=NOC(C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=N1 LQXFNPWWDRBZKT-UHFFFAOYSA-N 0.000 description 1
• LLJQFDXIOXMESP-UHFFFAOYSA-N 2-[[3-fluoro-5-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]methylamino]-2-methylpropanoic acid Chemical compound CC1=CC=CC=C1C1=CC=C(C=2ON=C(N=2)C=2C=C(CNC(C)(C)C(O)=O)C=C(F)C=2)C=C1C(F)(F)F LLJQFDXIOXMESP-UHFFFAOYSA-N 0.000 description 1
• YXXGGKALZZLHCX-UHFFFAOYSA-N 2-[ethyl-[[3-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]amino]-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)N(CC)CC1=CC=CC(C=2N=C(ON=2)C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=C1 YXXGGKALZZLHCX-UHFFFAOYSA-N 0.000 description 1
• JBMSNENQQYUCSY-KRWDZBQOSA-N 2-[methyl-[(1s)-1-[4-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]amino]acetic acid Chemical compound C1=CC([C@@H](N(C)CC(O)=O)C)=CC=C1C1=NOC(C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=N1 JBMSNENQQYUCSY-KRWDZBQOSA-N 0.000 description 1
• MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
• ZABVLYIZEBHGTJ-UHFFFAOYSA-N 2-aminobutanoic acid Chemical compound [CH2]CC(N)C(O)=O ZABVLYIZEBHGTJ-UHFFFAOYSA-N 0.000 description 1
• KMGUEILFFWDGFV-UHFFFAOYSA-N 2-benzoyl-2-benzoyloxy-3-hydroxybutanedioic acid Chemical compound C=1C=CC=CC=1C(=O)C(C(C(O)=O)O)(C(O)=O)OC(=O)C1=CC=CC=C1 KMGUEILFFWDGFV-UHFFFAOYSA-N 0.000 description 1
• XXSPGBOGLXKMDU-UHFFFAOYSA-M 2-bromo-2-methylpropanoate Chemical compound CC(C)(Br)C([O-])=O XXSPGBOGLXKMDU-UHFFFAOYSA-M 0.000 description 1
• BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
• 229940013085 2-diethylaminoethanol Drugs 0.000 description 1
• NJRXVEJTAYWCQJ-UHFFFAOYSA-L 2-mercaptosuccinate Chemical compound OC(=O)CC([S-])C([O-])=O NJRXVEJTAYWCQJ-UHFFFAOYSA-L 0.000 description 1
• LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
• 229940080296 2-naphthalenesulfonate Drugs 0.000 description 1
• WMPPDTMATNBGJN-UHFFFAOYSA-N 2-phenylethylbromide Chemical compound BrCCC1=CC=CC=C1 WMPPDTMATNBGJN-UHFFFAOYSA-N 0.000 description 1
• SDFBOAJVHGKEAO-UHFFFAOYSA-N 3-(2-hydroxyethyl)benzonitrile Chemical compound OCCC1=CC=CC(C#N)=C1 SDFBOAJVHGKEAO-UHFFFAOYSA-N 0.000 description 1
• FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
• PCOFIIVWHXIDGT-UHFFFAOYSA-N 3-(hydroxymethyl)benzonitrile Chemical compound OCC1=CC=CC(C#N)=C1 PCOFIIVWHXIDGT-UHFFFAOYSA-N 0.000 description 1
• KBRCDVSFCMVQSN-UHFFFAOYSA-N 3-(methylaminomethyl)benzonitrile Chemical compound CNCC1=CC=CC(C#N)=C1 KBRCDVSFCMVQSN-UHFFFAOYSA-N 0.000 description 1
• TWQWRHIQRAZHPR-XNXCGYEVSA-N 3-[2-[(8s,9r,10s,11s,13s,14s,16r,17r)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethoxy]carbonylbenzenesulfonic acid Chemical compound O=C([C@]1(O)[C@@]2(C)C[C@H](O)[C@]3(F)[C@@]4(C)C=CC(=O)C=C4CC[C@H]3[C@@H]2C[C@H]1C)COC(=O)C1=CC=CC(S(O)(=O)=O)=C1 TWQWRHIQRAZHPR-XNXCGYEVSA-N 0.000 description 1
• VZLWLSLMIKXXHL-UHFFFAOYSA-N 3-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]benzaldehyde Chemical compound CC1=CC=CC=C1C1=CC=C(C=2ON=C(N=2)C=2C=C(C=O)C=CC=2)C=C1C(F)(F)F VZLWLSLMIKXXHL-UHFFFAOYSA-N 0.000 description 1
• SBCFGFDAZCTSRH-UHFFFAOYSA-N 3-acetylbenzonitrile Chemical compound CC(=O)C1=CC=CC(C#N)=C1 SBCFGFDAZCTSRH-UHFFFAOYSA-N 0.000 description 1
• FEWJPZIEWOKRBE-UHFFFAOYSA-M 3-carboxy-2,3-dihydroxypropanoate Chemical compound OC(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-M 0.000 description 1
• XMIIGOLPHOKFCH-UHFFFAOYSA-M 3-phenylpropionate Chemical compound [O-]C(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-M 0.000 description 1
• AOJJSUZBOXZQNB-VTZDEGQISA-N 4'-epidoxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-VTZDEGQISA-N 0.000 description 1
• CANLULJYEHSQFU-UHFFFAOYSA-N 4-(1-aminoethyl)benzonitrile Chemical compound CC(N)C1=CC=C(C#N)C=C1 CANLULJYEHSQFU-UHFFFAOYSA-N 0.000 description 1
• XGAVOODMMBMCKV-UHFFFAOYSA-N 4-(1-hydroxyethyl)benzonitrile Chemical compound CC(O)C1=CC=C(C#N)C=C1 XGAVOODMMBMCKV-UHFFFAOYSA-N 0.000 description 1
• LJANCPRIUMHGJE-UHFFFAOYSA-N 4-(2-bromoacetyl)benzonitrile Chemical compound BrCC(=O)C1=CC=C(C#N)C=C1 LJANCPRIUMHGJE-UHFFFAOYSA-N 0.000 description 1
• RBSJBNYPTGMZIH-UHFFFAOYSA-N 4-(2-hydroxyethyl)benzonitrile Chemical compound OCCC1=CC=C(C#N)C=C1 RBSJBNYPTGMZIH-UHFFFAOYSA-N 0.000 description 1
• CANLULJYEHSQFU-SSDOTTSWSA-N 4-[(1r)-1-aminoethyl]benzonitrile Chemical compound C[C@@H](N)C1=CC=C(C#N)C=C1 CANLULJYEHSQFU-SSDOTTSWSA-N 0.000 description 1
• AFLWPAGYTPJSEY-CODXZCKSSA-N 4-[2-[(8s,9s,10r,11s,13s,14s,17r)-11,17-dihydroxy-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-oxoethoxy]-4-oxobutanoic acid;hydrate Chemical compound O.O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)COC(=O)CCC(O)=O)[C@@H]4[C@@H]3CCC2=C1 AFLWPAGYTPJSEY-CODXZCKSSA-N 0.000 description 1
• PDMMJQWZYJWABS-UHFFFAOYSA-N 4-acetylbenzonitrile 4-(1-hydroxyethyl)benzonitrile Chemical compound CC(O)C1=CC=C(C#N)C=C1.CC(=O)C1=CC=C(C#N)C=C1 PDMMJQWZYJWABS-UHFFFAOYSA-N 0.000 description 1
• GPBPFDPENZHCPR-UHFFFAOYSA-N 4-bromo-3-(trifluoromethyl)benzoic acid Chemical compound OC(=O)C1=CC=C(Br)C(C(F)(F)F)=C1 GPBPFDPENZHCPR-UHFFFAOYSA-N 0.000 description 1
• XAASLEJRGFPHEV-UHFFFAOYSA-N 4-cyanobenzyl alcohol Chemical compound OCC1=CC=C(C#N)C=C1 XAASLEJRGFPHEV-UHFFFAOYSA-N 0.000 description 1
• HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
• XOKDXPVXJWTSRM-UHFFFAOYSA-N 4-iodobenzonitrile Chemical compound IC1=CC=C(C#N)C=C1 XOKDXPVXJWTSRM-UHFFFAOYSA-N 0.000 description 1
• 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
• WICPCYDDNAFZLB-UHFFFAOYSA-N 5-methyl-4-phenyl-5-(trifluoromethyl)cyclohexa-1,3-diene-1-carboxylic acid Chemical compound CC1(C(=CC=C(C1)C(=O)O)C1=CC=CC=C1)C(F)(F)F WICPCYDDNAFZLB-UHFFFAOYSA-N 0.000 description 1
• GWKQSBXDFHODNU-UQPSFNCESA-N 6z83r2hm9l Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)COC(=O)CCC(O)=O)[C@@]1(C)C[C@@H]2O GWKQSBXDFHODNU-UQPSFNCESA-N 0.000 description 1
• OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 1
• 208000030507 AIDS Diseases 0.000 description 1
• 208000002874 Acne Vulgaris Diseases 0.000 description 1
• 208000009304 Acute Kidney Injury Diseases 0.000 description 1
• 208000007788 Acute Liver Failure Diseases 0.000 description 1
• 206010000804 Acute hepatic failure Diseases 0.000 description 1
• 208000026872 Addison Disease Diseases 0.000 description 1
• 201000010000 Agranulocytosis Diseases 0.000 description 1
• 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 1
• 239000005995 Aluminium silicate Substances 0.000 description 1
• 208000024827 Alzheimer disease Diseases 0.000 description 1
• USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
• 239000005695 Ammonium acetate Substances 0.000 description 1
• 206010002065 Anaemia megaloblastic Diseases 0.000 description 1
• 206010002091 Anaesthesia Diseases 0.000 description 1
• 208000028185 Angioedema Diseases 0.000 description 1
• 206010002660 Anoxia Diseases 0.000 description 1
• 241000976983 Anoxia Species 0.000 description 1
• 240000004178 Anthoxanthum odoratum Species 0.000 description 1
• 239000004475 Arginine Substances 0.000 description 1
• 102000015790 Asparaginase Human genes 0.000 description 1
• 108010024976 Asparaginase Proteins 0.000 description 1
• 241000416162 Astragalus gummifer Species 0.000 description 1
• 208000032116 Autoimmune Experimental Encephalomyelitis Diseases 0.000 description 1
• 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 description 1
• 208000035143 Bacterial infection Diseases 0.000 description 1
• 208000023328 Basedow disease Diseases 0.000 description 1
• KUVIULQEHSCUHY-XYWKZLDCSA-N Beclometasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)COC(=O)CC)(OC(=O)CC)[C@@]1(C)C[C@@H]2O KUVIULQEHSCUHY-XYWKZLDCSA-N 0.000 description 1
• GUBGYTABKSRVRQ-DCSYEGIMSA-N Beta-Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-DCSYEGIMSA-N 0.000 description 1
• 208000033222 Biliary cirrhosis primary Diseases 0.000 description 1
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
• BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
• 241000283725 Bos Species 0.000 description 1
• VOVIALXJUBGFJZ-KWVAZRHASA-N Budesonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(CCC)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O VOVIALXJUBGFJZ-KWVAZRHASA-N 0.000 description 1
• RBXSRBUKCAOSBO-UHFFFAOYSA-N C(C)(=O)C1=CC=C(C#N)C=C1.C(#N)C=1C=C(C=CC1)C(C)NCC(=O)OC(C)(C)C Chemical compound C(C)(=O)C1=CC=C(C#N)C=C1.C(#N)C=1C=C(C=CC1)C(C)NCC(=O)OC(C)(C)C RBXSRBUKCAOSBO-UHFFFAOYSA-N 0.000 description 1
• 101150013553 CD40 gene Proteins 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
• 208000005623 Carcinogenesis Diseases 0.000 description 1
• 201000009030 Carcinoma Diseases 0.000 description 1
• 208000031229 Cardiomyopathies Diseases 0.000 description 1
• 229920002284 Cellulose triacetate Polymers 0.000 description 1
• 206010008609 Cholangitis sclerosing Diseases 0.000 description 1
• 208000002691 Choroiditis Diseases 0.000 description 1
• 206010009208 Cirrhosis alcoholic Diseases 0.000 description 1
• 206010009657 Clostridium difficile colitis Diseases 0.000 description 1
• 208000015943 Coeliac disease Diseases 0.000 description 1
• 206010010744 Conjunctivitis allergic Diseases 0.000 description 1
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
• 206010066968 Corneal leukoma Diseases 0.000 description 1
• ITRJWOMZKQRYTA-RFZYENFJSA-N Cortisone acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)C)(O)[C@@]1(C)CC2=O ITRJWOMZKQRYTA-RFZYENFJSA-N 0.000 description 1
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
• 108010036941 Cyclosporins Proteins 0.000 description 1
• UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 description 1
• 241000701022 Cytomegalovirus Species 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-M D-alaninate Chemical compound C[C@@H](N)C([O-])=O QNAYBMKLOCPYGJ-UWTATZPHSA-M 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
• 206010012442 Dermatitis contact Diseases 0.000 description 1
• PQVDYPCHUGFHAR-PKWREOPISA-N Dexamethasone Tebutate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)COC(=O)CC(C)(C)C)(O)[C@@]1(C)C[C@@H]2O PQVDYPCHUGFHAR-PKWREOPISA-N 0.000 description 1
• 208000007342 Diabetic Nephropathies Diseases 0.000 description 1
• 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
• XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
• HHJIUUAMYGBVSD-YTFFSALGSA-N Diflucortolone valerate Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@H](C(=O)COC(=O)CCCC)[C@@]2(C)C[C@@H]1O HHJIUUAMYGBVSD-YTFFSALGSA-N 0.000 description 1
• WYQPLTPSGFELIB-JTQPXKBDSA-N Difluprednate Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2CC[C@@](C(=O)COC(C)=O)(OC(=O)CCC)[C@@]2(C)C[C@@H]1O WYQPLTPSGFELIB-JTQPXKBDSA-N 0.000 description 1
• QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
• 102000036530 EDG receptors Human genes 0.000 description 1
• 108091007263 EDG receptors Proteins 0.000 description 1
• 206010014561 Emphysema Diseases 0.000 description 1
• 241000792859 Enema Species 0.000 description 1
• 206010014950 Eosinophilia Diseases 0.000 description 1
• 206010014989 Epidermolysis bullosa Diseases 0.000 description 1
• 206010015150 Erythema Diseases 0.000 description 1
• 206010015218 Erythema multiforme Diseases 0.000 description 1
• SCOLLNGEVAYHCD-UHFFFAOYSA-N FC=1C=C(C#N)C=C(C1)C.BrCC=1C=C(C#N)C=C(C1)F Chemical compound FC=1C=C(C#N)C=C(C1)C.BrCC=1C=C(C#N)C=C(C1)F SCOLLNGEVAYHCD-UHFFFAOYSA-N 0.000 description 1
• 206010016228 Fasciitis Diseases 0.000 description 1
• CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
• 206010016654 Fibrosis Diseases 0.000 description 1
• WJOHZNCJWYWUJD-IUGZLZTKSA-N Fluocinonide Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)COC(=O)C)[C@@]2(C)C[C@@H]1O WJOHZNCJWYWUJD-IUGZLZTKSA-N 0.000 description 1
• WHZRCUIISKRTJL-YTZKRAOUSA-N Fluocortolone caproate Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@@H](C)[C@H](C(=O)COC(=O)CCCCC)[C@@]2(C)C[C@@H]1O WHZRCUIISKRTJL-YTZKRAOUSA-N 0.000 description 1
• POPFMWWJOGLOIF-XWCQMRHXSA-N Flurandrenolide Chemical compound C1([C@@H](F)C2)=CC(=O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O POPFMWWJOGLOIF-XWCQMRHXSA-N 0.000 description 1
• BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
• DSLZVSRJTYRBFB-UHFFFAOYSA-N Galactaric acid Natural products OC(=O)C(O)C(O)C(O)C(O)C(O)=O DSLZVSRJTYRBFB-UHFFFAOYSA-N 0.000 description 1
• 241000206672 Gelidium Species 0.000 description 1
• AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 1
• 208000024869 Goodpasture syndrome Diseases 0.000 description 1
• 206010018691 Granuloma Diseases 0.000 description 1
• 108010043121 Green Fluorescent Proteins Proteins 0.000 description 1
• 102000004144 Green Fluorescent Proteins Human genes 0.000 description 1
• 208000035895 Guillain-Barré syndrome Diseases 0.000 description 1
• MUQNGPZZQDCDFT-JNQJZLCISA-N Halcinonide Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CCl)[C@@]1(C)C[C@@H]2O MUQNGPZZQDCDFT-JNQJZLCISA-N 0.000 description 1
• 208000030836 Hashimoto thyroiditis Diseases 0.000 description 1
• 208000035186 Hemolytic Autoimmune Anemia Diseases 0.000 description 1
• 208000032759 Hemolytic-Uremic Syndrome Diseases 0.000 description 1
• 208000005100 Herpetic Keratitis Diseases 0.000 description 1
• 101001057504 Homo sapiens Interferon-stimulated gene 20 kDa protein Proteins 0.000 description 1
• 101001055144 Homo sapiens Interleukin-2 receptor subunit alpha Proteins 0.000 description 1
• 101001063392 Homo sapiens Lymphocyte function-associated antigen 3 Proteins 0.000 description 1
• 101100236683 Homo sapiens MBTPS1 gene Proteins 0.000 description 1
• 101000738771 Homo sapiens Receptor-type tyrosine-protein phosphatase C Proteins 0.000 description 1
• 101000914514 Homo sapiens T-cell-specific surface glycoprotein CD28 Proteins 0.000 description 1
• 206010020850 Hyperthyroidism Diseases 0.000 description 1
• 206010021074 Hypoplastic anaemia Diseases 0.000 description 1
• 206010021143 Hypoxia Diseases 0.000 description 1
• 201000003838 Idiopathic interstitial pneumonia Diseases 0.000 description 1
• 206010021245 Idiopathic thrombocytopenic purpura Diseases 0.000 description 1
• 206010021639 Incontinence Diseases 0.000 description 1
• 108010008212 Integrin alpha4beta1 Proteins 0.000 description 1
• 102100026878 Interleukin-2 receptor subunit alpha Human genes 0.000 description 1
• LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 1
• PIWKPBJCKXDKJR-UHFFFAOYSA-N Isoflurane Chemical compound FC(F)OC(Cl)C(F)(F)F PIWKPBJCKXDKJR-UHFFFAOYSA-N 0.000 description 1
• 201000002287 Keratoconus Diseases 0.000 description 1
• ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 1
• 229930064664 L-arginine Natural products 0.000 description 1
• 235000014852 L-arginine Nutrition 0.000 description 1
• ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
• CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
• WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
• HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-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
• 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
• 240000007472 Leucaena leucocephala Species 0.000 description 1
• 206010024380 Leukoderma Diseases 0.000 description 1
• NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 1
• 208000012309 Linear IgA disease Diseases 0.000 description 1
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
• 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
• 102100030984 Lymphocyte function-associated antigen 3 Human genes 0.000 description 1
• 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 description 1
• 206010025323 Lymphomas Diseases 0.000 description 1
• 206010025327 Lymphopenia Diseases 0.000 description 1
• 241000701076 Macacine alphaherpesvirus 1 Species 0.000 description 1
• OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
• 229930195725 Mannitol Natural products 0.000 description 1
• 208000000682 Megaloblastic Anemia Diseases 0.000 description 1
• 208000027530 Meniere disease Diseases 0.000 description 1
• 206010027476 Metastases Diseases 0.000 description 1
• CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
• FQISKWAFAHGMGT-SGJOWKDISA-M Methylprednisolone sodium succinate Chemical compound [Na+].C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)[C@@](O)(C(=O)COC(=O)CCC([O-])=O)CC[C@H]21 FQISKWAFAHGMGT-SGJOWKDISA-M 0.000 description 1
• 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
• 208000019695 Migraine disease Diseases 0.000 description 1
• 206010049567 Miller Fisher syndrome Diseases 0.000 description 1
• HZQDCMWJEBCWBR-UUOKFMHZSA-N Mizoribine Chemical compound OC1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 HZQDCMWJEBCWBR-UUOKFMHZSA-N 0.000 description 1
• 206010027910 Mononeuritis Diseases 0.000 description 1
• 208000024599 Mooren ulcer Diseases 0.000 description 1
• 229920000715 Mucilage Polymers 0.000 description 1
• 241000187479 Mycobacterium tuberculosis Species 0.000 description 1
• NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
• UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
• HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
• HIEKJRVYXXINKH-ADVKXBNGSA-N N1([C@H]2CC[C@H](C[C@H]2OC)/C=C(\C)[C@H]2OC(=O)[C@@H]3CCCCN3C(=O)C(=O)[C@]3(O)O[C@@H]([C@H](C[C@H]3C)OC)[C@@H](OC)C[C@@H](C)C/C(C)=C/[C@H](C(C[C@H](O)[C@H]2C)=O)CC)C=NN=N1 Chemical compound N1([C@H]2CC[C@H](C[C@H]2OC)/C=C(\C)[C@H]2OC(=O)[C@@H]3CCCCN3C(=O)C(=O)[C@]3(O)O[C@@H]([C@H](C[C@H]3C)OC)[C@@H](OC)C[C@@H](C)C/C(C)=C/[C@H](C(C[C@H](O)[C@H]2C)=O)CC)C=NN=N1 HIEKJRVYXXINKH-ADVKXBNGSA-N 0.000 description 1
• ZMKGDQSIRSGUDJ-UHFFFAOYSA-N NVa2 cyclosporine Natural products CCCC1NC(=O)C(C(O)C(C)CC=CC)N(C)C(=O)C(C(C)C)N(C)C(=O)C(CC(C)C)N(C)C(=O)C(CC(C)C)N(C)C(=O)C(C)NC(=O)C(C)NC(=O)C(CC(C)C)N(C)C(=O)C(C(C)C)NC(=O)C(CC(C)C)N(C)C(=O)CN(C)C1=O ZMKGDQSIRSGUDJ-UHFFFAOYSA-N 0.000 description 1
• 206010051606 Necrotising colitis Diseases 0.000 description 1
• 208000012902 Nervous system disease Diseases 0.000 description 1
• PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
• KNTFCRCCPLEUQZ-VKHMYHEASA-N O-methylserine Chemical compound COC[C@H](N)C(O)=O KNTFCRCCPLEUQZ-VKHMYHEASA-N 0.000 description 1
• 208000008589 Obesity Diseases 0.000 description 1
• REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
• 108010038807 Oligopeptides Proteins 0.000 description 1
• 102000015636 Oligopeptides Human genes 0.000 description 1
• 206010073938 Ophthalmic herpes simplex Diseases 0.000 description 1
• 241000353355 Oreosoma atlanticum Species 0.000 description 1
• 208000001132 Osteoporosis Diseases 0.000 description 1
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
• 206010033645 Pancreatitis Diseases 0.000 description 1
• HYRKAAMZBDSJFJ-LFDBJOOHSA-N Paramethasone acetate Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)COC(C)=O)(O)[C@@]2(C)C[C@@H]1O HYRKAAMZBDSJFJ-LFDBJOOHSA-N 0.000 description 1
• 241000721454 Pemphigus Species 0.000 description 1
• 229930182555 Penicillin Natural products 0.000 description 1
• JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
• 208000031845 Pernicious anaemia Diseases 0.000 description 1
• NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
• 108010039918 Polylysine Proteins 0.000 description 1
• 206010036105 Polyneuropathy Diseases 0.000 description 1
• 208000003971 Posterior uveitis Diseases 0.000 description 1
• LRJOMUJRLNCICJ-JZYPGELDSA-N Prednisolone acetate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)C)(O)[C@@]1(C)C[C@@H]2O LRJOMUJRLNCICJ-JZYPGELDSA-N 0.000 description 1
• 208000012654 Primary biliary cholangitis Diseases 0.000 description 1
• 206010036774 Proctitis Diseases 0.000 description 1
• 208000003100 Pseudomembranous Enterocolitis Diseases 0.000 description 1
• 206010037128 Pseudomembranous colitis Diseases 0.000 description 1
• 208000003670 Pure Red-Cell Aplasia Diseases 0.000 description 1
• 208000006311 Pyoderma Diseases 0.000 description 1
• IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
• 206010037779 Radiculopathy Diseases 0.000 description 1
• 102100037422 Receptor-type tyrosine-protein phosphatase C Human genes 0.000 description 1
• 208000033626 Renal failure acute Diseases 0.000 description 1
• 206010063837 Reperfusion injury Diseases 0.000 description 1
• 208000002200 Respiratory Hypersensitivity Diseases 0.000 description 1
• 208000007014 Retinitis pigmentosa Diseases 0.000 description 1
• 241000283984 Rodentia Species 0.000 description 1
• 101150043606 S1pr5 gene Proteins 0.000 description 1
• 206010039705 Scleritis Diseases 0.000 description 1
• 206010039793 Seborrhoeic dermatitis Diseases 0.000 description 1
• 206010039966 Senile dementia Diseases 0.000 description 1
• 206010040047 Sepsis Diseases 0.000 description 1
• 206010040070 Septic Shock Diseases 0.000 description 1
• 241000872198 Serjania polyphylla Species 0.000 description 1
• 108010071390 Serum Albumin Proteins 0.000 description 1
• 102000007562 Serum Albumin Human genes 0.000 description 1
• 229920001800 Shellac Polymers 0.000 description 1
• 208000021386 Sjogren Syndrome Diseases 0.000 description 1
• VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
• 239000004280 Sodium formate Substances 0.000 description 1
• BCKXLBQYZLBQEK-KVVVOXFISA-M Sodium oleate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC([O-])=O BCKXLBQYZLBQEK-KVVVOXFISA-M 0.000 description 1
• 102100029802 Sphingosine 1-phosphate receptor 5 Human genes 0.000 description 1
• 235000021355 Stearic acid Nutrition 0.000 description 1
• 208000007107 Stomach Ulcer Diseases 0.000 description 1
• 241001415801 Sulidae Species 0.000 description 1
• 238000006859 Swern oxidation reaction Methods 0.000 description 1
• 208000031673 T-Cell Cutaneous Lymphoma Diseases 0.000 description 1
• 102100027213 T-cell-specific surface glycoprotein CD28 Human genes 0.000 description 1
• 239000012317 TBTU Substances 0.000 description 1
• 208000001106 Takayasu Arteritis Diseases 0.000 description 1
• FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
• 206010053615 Thermal burn Diseases 0.000 description 1
• FOCVUCIESVLUNU-UHFFFAOYSA-N Thiotepa Chemical compound C1CN1P(N1CC1)(=S)N1CC1 FOCVUCIESVLUNU-UHFFFAOYSA-N 0.000 description 1
• 208000031981 Thrombocytopenic Idiopathic Purpura Diseases 0.000 description 1
• 208000007536 Thrombosis Diseases 0.000 description 1
• 231100000579 Toxinosis Toxicity 0.000 description 1
• 229920001615 Tragacanth Polymers 0.000 description 1
• 206010052779 Transplant rejections Diseases 0.000 description 1
• XGMPVBXKDAHORN-RBWIMXSLSA-N Triamcinolone diacetate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](OC(C)=O)[C@@](C(=O)COC(=O)C)(O)[C@@]1(C)C[C@@H]2O XGMPVBXKDAHORN-RBWIMXSLSA-N 0.000 description 1
• TZIZWYVVGLXXFV-FLRHRWPCSA-N Triamcinolone hexacetonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)COC(=O)CC(C)(C)C)[C@@]1(C)C[C@@H]2O TZIZWYVVGLXXFV-FLRHRWPCSA-N 0.000 description 1
• 239000007983 Tris buffer Substances 0.000 description 1
• 102100040245 Tumor necrosis factor receptor superfamily member 5 Human genes 0.000 description 1
• 206010064996 Ulcerative keratitis Diseases 0.000 description 1
• 208000024780 Urticaria Diseases 0.000 description 1
• 208000001445 Uveomeningoencephalitic Syndrome Diseases 0.000 description 1
• 206010047115 Vasculitis Diseases 0.000 description 1
• 208000034705 Vogt-Koyanagi-Harada syndrome Diseases 0.000 description 1
• 240000008042 Zea mays Species 0.000 description 1
• 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
• NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
• JNSBEPKGFVENFS-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]boronic acid Chemical compound OB(O)C1=CC=CC=C1C(F)(F)F JNSBEPKGFVENFS-UHFFFAOYSA-N 0.000 description 1
• DPHFJXVKASDMBW-RQRKFSSASA-N [2-[(8s,9r,10s,11s,13s,14s,16r,17r)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate;hydrate Chemical compound O.C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)COC(C)=O)(O)[C@@]1(C)C[C@@H]2O DPHFJXVKASDMBW-RQRKFSSASA-N 0.000 description 1
• WBNNIURTBZHJTI-WDCKKOMHSA-N [2-[(8s,9s,10r,11s,13s,14s,17r)-11,17-dihydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] dihydrogen phosphate;2-[(2-propan-2-ylphenoxy)methyl]-4,5-dihydro-1h-imidazole Chemical compound CC(C)C1=CC=CC=C1OCC1=NCCN1.O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)COP(O)(O)=O)[C@@H]4[C@@H]3CCC2=C1 WBNNIURTBZHJTI-WDCKKOMHSA-N 0.000 description 1
• DNSAKUGJOSFARZ-FOMYWIRZSA-N [2-[(8s,9s,10r,11s,13s,14s,17r)-11,17-dihydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] hexanoate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)CCCCC)(O)[C@@]1(C)C[C@@H]2O DNSAKUGJOSFARZ-FOMYWIRZSA-N 0.000 description 1
• CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 1
• WXIONIWNXBAHRU-UHFFFAOYSA-N [dimethylamino(triazolo[4,5-b]pyridin-3-yloxy)methylidene]-dimethylazanium Chemical compound C1=CN=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 WXIONIWNXBAHRU-UHFFFAOYSA-N 0.000 description 1
• 239000003655 absorption accelerator Substances 0.000 description 1
• IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 1
• MGVGMXLGOKTYKP-ZFOBEOMCSA-N acetic acid;(6s,8s,9s,10r,11s,13s,14s,17r)-11,17-dihydroxy-17-(2-hydroxyacetyl)-6,10,13-trimethyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthren-3-one Chemical compound CC(O)=O.C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)[C@@](O)(C(=O)CO)CC[C@H]21 MGVGMXLGOKTYKP-ZFOBEOMCSA-N 0.000 description 1
• DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
• 206010000496 acne Diseases 0.000 description 1
• RJURFGZVJUQBHK-IIXSONLDSA-N actinomycin D Chemical compound C[C@H]1OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C(=O)[C@@H]2CCCN2C(=O)[C@@H](C(C)C)NC(=O)[C@H]1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)N[C@@H]4C(=O)N[C@@H](C(N5CCC[C@H]5C(=O)N(C)CC(=O)N(C)[C@@H](C(C)C)C(=O)O[C@@H]4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-IIXSONLDSA-N 0.000 description 1
• 239000008186 active pharmaceutical agent Substances 0.000 description 1
• 230000001154 acute effect Effects 0.000 description 1
• 238000005917 acylation reaction Methods 0.000 description 1
• 239000000853 adhesive Substances 0.000 description 1
• WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
• 239000008272 agar Substances 0.000 description 1
• 206010064930 age-related macular degeneration Diseases 0.000 description 1
• 230000032683 aging Effects 0.000 description 1
• 230000010085 airway hyperresponsiveness Effects 0.000 description 1
• 235000004279 alanine Nutrition 0.000 description 1
• 229960004229 alclometasone dipropionate Drugs 0.000 description 1
• DJHCCTTVDRAMEH-DUUJBDRPSA-N alclometasone dipropionate Chemical compound C([C@H]1Cl)C2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)COC(=O)CC)(OC(=O)CC)[C@@]1(C)C[C@@H]2O DJHCCTTVDRAMEH-DUUJBDRPSA-N 0.000 description 1
• 125000003158 alcohol group Chemical group 0.000 description 1
• 208000010002 alcoholic liver cirrhosis Diseases 0.000 description 1
• 125000001931 aliphatic group Chemical group 0.000 description 1
• 239000003513 alkali Substances 0.000 description 1
• 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
• 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
• 150000001347 alkyl bromides Chemical class 0.000 description 1
• 150000001350 alkyl halides Chemical class 0.000 description 1
• 150000008052 alkyl sulfonates Chemical class 0.000 description 1
• 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 1
• 230000029936 alkylation Effects 0.000 description 1
• 238000005804 alkylation reaction Methods 0.000 description 1
• 201000009961 allergic asthma Diseases 0.000 description 1
• 208000002205 allergic conjunctivitis Diseases 0.000 description 1
• 231100000360 alopecia Toxicity 0.000 description 1
• 208000004631 alopecia areata Diseases 0.000 description 1
• AEMOLEFTQBMNLQ-BKBMJHBISA-N alpha-D-galacturonic acid Chemical compound O[C@H]1O[C@H](C(O)=O)[C@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-BKBMJHBISA-N 0.000 description 1
• AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 description 1
• 239000004411 aluminium Substances 0.000 description 1
• 229910052782 aluminium Inorganic materials 0.000 description 1
• XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
• 235000012211 aluminium silicate Nutrition 0.000 description 1
• 229960003099 amcinonide Drugs 0.000 description 1
• ILKJAFIWWBXGDU-MOGDOJJUSA-N amcinonide Chemical compound O([C@@]1([C@H](O2)C[C@@H]3[C@@]1(C[C@H](O)[C@]1(F)[C@@]4(C)C=CC(=O)C=C4CC[C@H]13)C)C(=O)COC(=O)C)C12CCCC1 ILKJAFIWWBXGDU-MOGDOJJUSA-N 0.000 description 1
• 150000003862 amino acid derivatives Chemical class 0.000 description 1
• 229960000510 ammonia Drugs 0.000 description 1
• 229910021529 ammonia Inorganic materials 0.000 description 1
• 235000019257 ammonium acetate Nutrition 0.000 description 1
• 229940043376 ammonium acetate Drugs 0.000 description 1
• VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
• XCPGHVQEEXUHNC-UHFFFAOYSA-N amsacrine Chemical compound COC1=CC(NS(C)(=O)=O)=CC=C1NC1=C(C=CC=C2)C2=NC2=CC=CC=C12 XCPGHVQEEXUHNC-UHFFFAOYSA-N 0.000 description 1
• 229960001220 amsacrine Drugs 0.000 description 1
• 230000037005 anaesthesia Effects 0.000 description 1
• 150000008064 anhydrides Chemical class 0.000 description 1
• 238000010171 animal model Methods 0.000 description 1
• 230000007953 anoxia Effects 0.000 description 1
• 239000005557 antagonist Substances 0.000 description 1
• 239000003963 antioxidant agent Substances 0.000 description 1
• 235000006708 antioxidants Nutrition 0.000 description 1
• 238000013459 approach Methods 0.000 description 1
• 239000012736 aqueous medium Substances 0.000 description 1
• 239000003125 aqueous solvent Substances 0.000 description 1
• ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
• 229960003121 arginine Drugs 0.000 description 1
• 235000009697 arginine Nutrition 0.000 description 1
• 125000003435 aroyl group Chemical group 0.000 description 1
• 239000008122 artificial sweetener Substances 0.000 description 1
• 235000021311 artificial sweeteners Nutrition 0.000 description 1
• 150000001499 aryl bromides Chemical class 0.000 description 1
• 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 1
• 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
• 125000005279 aryl sulfonyloxy group Chemical group 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
• 229960003272 asparaginase Drugs 0.000 description 1
• DCXYFEDJOCDNAF-UHFFFAOYSA-M asparaginate Chemical compound [O-]C(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-M 0.000 description 1
• 229940009098 aspartate Drugs 0.000 description 1
• 230000003416 augmentation Effects 0.000 description 1
• 201000000448 autoimmune hemolytic anemia Diseases 0.000 description 1
• 201000003710 autoimmune thrombocytopenic purpura Diseases 0.000 description 1
• 229960002170 azathioprine Drugs 0.000 description 1
• LMEKQMALGUDUQG-UHFFFAOYSA-N azathioprine Chemical compound CN1C=NC([N+]([O-])=O)=C1SC1=NC=NC2=C1NC=N2 LMEKQMALGUDUQG-UHFFFAOYSA-N 0.000 description 1
• 208000022362 bacterial infectious disease Diseases 0.000 description 1
• 239000000022 bacteriostatic agent Substances 0.000 description 1
• 230000003385 bacteriostatic effect Effects 0.000 description 1
• 150000007514 bases Chemical class 0.000 description 1
• 229960004669 basiliximab Drugs 0.000 description 1
• 229950000210 beclometasone dipropionate Drugs 0.000 description 1
• 230000008901 benefit Effects 0.000 description 1
• UPABQMWFWCMOFV-UHFFFAOYSA-N benethamine Chemical compound C=1C=CC=CC=1CNCCC1=CC=CC=C1 UPABQMWFWCMOFV-UHFFFAOYSA-N 0.000 description 1
• 150000003935 benzaldehydes Chemical class 0.000 description 1
• SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
• 150000008359 benzonitriles Chemical class 0.000 description 1
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
• KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
• 229940073608 benzyl chloride Drugs 0.000 description 1
• 238000005574 benzylation reaction Methods 0.000 description 1
• MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-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
• 229960002537 betamethasone Drugs 0.000 description 1
• UREBDLICKHMUKA-DVTGEIKXSA-N betamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-DVTGEIKXSA-N 0.000 description 1
• 229960004648 betamethasone acetate Drugs 0.000 description 1
• AKUJBENLRBOFTD-QZIXMDIESA-N betamethasone acetate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)COC(C)=O)(O)[C@@]1(C)C[C@@H]2O AKUJBENLRBOFTD-QZIXMDIESA-N 0.000 description 1
• 229960001102 betamethasone dipropionate Drugs 0.000 description 1
• CIWBQSYVNNPZIQ-XYWKZLDCSA-N betamethasone dipropionate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)COC(=O)CC)(OC(=O)CC)[C@@]1(C)C[C@@H]2O CIWBQSYVNNPZIQ-XYWKZLDCSA-N 0.000 description 1
• VQODGRNSFPNSQE-DVTGEIKXSA-N betamethasone phosphate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)COP(O)(O)=O)(O)[C@@]1(C)C[C@@H]2O VQODGRNSFPNSQE-DVTGEIKXSA-N 0.000 description 1
• 229950006991 betamethasone phosphate Drugs 0.000 description 1
• 229960004311 betamethasone valerate Drugs 0.000 description 1
• SNHRLVCMMWUAJD-SUYDQAKGSA-N betamethasone valerate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(OC(=O)CCCC)[C@@]1(C)C[C@@H]2O SNHRLVCMMWUAJD-SUYDQAKGSA-N 0.000 description 1
• MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 1
• 230000000975 bioactive effect Effects 0.000 description 1
• 230000033228 biological regulation Effects 0.000 description 1
• 239000004305 biphenyl Substances 0.000 description 1
• 235000010290 biphenyl Nutrition 0.000 description 1
• 229920001400 block copolymer Polymers 0.000 description 1
• 230000000903 blocking effect Effects 0.000 description 1
• 238000010241 blood sampling Methods 0.000 description 1
• 210000000988 bone and bone Anatomy 0.000 description 1
• 210000001185 bone marrow Anatomy 0.000 description 1
• 201000008873 bone osteosarcoma Diseases 0.000 description 1
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
• 206010006451 bronchitis Diseases 0.000 description 1
• 229960004436 budesonide Drugs 0.000 description 1
• 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• FGNLEIGUMSBZQP-UHFFFAOYSA-N cadaverine dihydrochloride Chemical compound Cl.Cl.NCCCCCN FGNLEIGUMSBZQP-UHFFFAOYSA-N 0.000 description 1
• 229960001948 caffeine Drugs 0.000 description 1
• VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 1
• 229910000019 calcium carbonate Inorganic materials 0.000 description 1
• AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
• 239000000920 calcium hydroxide Substances 0.000 description 1
• 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
• 239000001506 calcium phosphate Substances 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
• 235000013539 calcium stearate Nutrition 0.000 description 1
• 239000008116 calcium stearate Substances 0.000 description 1
• MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical class C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
• 201000011510 cancer Diseases 0.000 description 1
• 230000036952 cancer formation Effects 0.000 description 1
• FAKRSMQSSFJEIM-RQJHMYQMSA-N captopril Chemical compound SC[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O FAKRSMQSSFJEIM-RQJHMYQMSA-N 0.000 description 1
• 229960000830 captopril Drugs 0.000 description 1
• 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 1
• 125000001589 carboacyl group Chemical group 0.000 description 1
• 229940105329 carboxymethylcellulose Drugs 0.000 description 1
• 231100000504 carcinogenesis Toxicity 0.000 description 1
• 238000005266 casting Methods 0.000 description 1
• 230000003915 cell function Effects 0.000 description 1
• 239000001913 cellulose Substances 0.000 description 1
• 229920002678 cellulose Polymers 0.000 description 1
• 235000010980 cellulose Nutrition 0.000 description 1
• 239000004568 cement Substances 0.000 description 1
• 238000005119 centrifugation Methods 0.000 description 1
• 239000007795 chemical reaction product Substances 0.000 description 1
• 239000007810 chemical reaction solvent Substances 0.000 description 1
• 210000004978 chinese hamster ovary cell Anatomy 0.000 description 1
• KVSASDOGYIBWTA-UHFFFAOYSA-N chloro benzoate Chemical compound ClOC(=O)C1=CC=CC=C1 KVSASDOGYIBWTA-UHFFFAOYSA-N 0.000 description 1
• 235000012000 cholesterol Nutrition 0.000 description 1
• 208000020832 chronic kidney disease Diseases 0.000 description 1
• 208000032852 chronic lymphocytic leukemia Diseases 0.000 description 1
• 208000025302 chronic primary adrenal insufficiency Diseases 0.000 description 1
• 201000010002 cicatricial pemphigoid Diseases 0.000 description 1
• 229940114081 cinnamate Drugs 0.000 description 1
• 230000007882 cirrhosis Effects 0.000 description 1
• 208000019425 cirrhosis of liver Diseases 0.000 description 1
• 238000003776 cleavage reaction Methods 0.000 description 1
• 229960004703 clobetasol propionate Drugs 0.000 description 1
• CBGUOGMQLZIXBE-XGQKBEPLSA-N clobetasol propionate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CCl)(OC(=O)CC)[C@@]1(C)C[C@@H]2O CBGUOGMQLZIXBE-XGQKBEPLSA-N 0.000 description 1
• 239000011248 coating agent Substances 0.000 description 1
• 206010009887 colitis Diseases 0.000 description 1
• 239000000470 constituent Substances 0.000 description 1
• 208000010247 contact dermatitis Diseases 0.000 description 1
• 238000013270 controlled release Methods 0.000 description 1
• 238000007796 conventional method Methods 0.000 description 1
• 229920001577 copolymer Polymers 0.000 description 1
• 229910052802 copper Inorganic materials 0.000 description 1
• 239000010949 copper Substances 0.000 description 1
• 239000003246 corticosteroid Substances 0.000 description 1
• 229960001334 corticosteroids Drugs 0.000 description 1
• BMCQMVFGOVHVNG-TUFAYURCSA-N cortisol 17-butyrate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)CO)(OC(=O)CCC)[C@@]1(C)C[C@@H]2O BMCQMVFGOVHVNG-TUFAYURCSA-N 0.000 description 1
• ALEXXDVDDISNDU-JZYPGELDSA-N cortisol 21-acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)C)(O)[C@@]1(C)C[C@@H]2O ALEXXDVDDISNDU-JZYPGELDSA-N 0.000 description 1
• 229960003290 cortisone acetate Drugs 0.000 description 1
• 229960003840 cortivazol Drugs 0.000 description 1
• RKHQGWMMUURILY-UHRZLXHJSA-N cortivazol Chemical compound C([C@H]1[C@@H]2C[C@H]([C@]([C@@]2(C)C[C@H](O)[C@@H]1[C@@]1(C)C2)(O)C(=O)COC(C)=O)C)=C(C)C1=CC1=C2C=NN1C1=CC=CC=C1 RKHQGWMMUURILY-UHRZLXHJSA-N 0.000 description 1
• 239000006184 cosolvent Substances 0.000 description 1
• 239000007822 coupling agent Substances 0.000 description 1
• 238000006880 cross-coupling reaction Methods 0.000 description 1
• 239000013078 crystal Substances 0.000 description 1
• 238000009109 curative therapy Methods 0.000 description 1
• 238000011461 current therapy Methods 0.000 description 1
• 201000007241 cutaneous T cell lymphoma Diseases 0.000 description 1
• 229940109275 cyclamate Drugs 0.000 description 1
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
• 229930182912 cyclosporin Natural products 0.000 description 1
• 108010019249 cyclosporin G Proteins 0.000 description 1
• 229960000684 cytarabine Drugs 0.000 description 1
• 229960002806 daclizumab Drugs 0.000 description 1
• GHVNFZFCNZKVNT-UHFFFAOYSA-M decanoate Chemical compound CCCCCCCCCC([O-])=O GHVNFZFCNZKVNT-UHFFFAOYSA-M 0.000 description 1
• 230000006837 decompression Effects 0.000 description 1
• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 230000018044 dehydration Effects 0.000 description 1
• 238000006297 dehydration reaction Methods 0.000 description 1
• 201000001981 dermatomyositis Diseases 0.000 description 1
• 238000000586 desensitisation Methods 0.000 description 1
• 229960003662 desonide Drugs 0.000 description 1
• WBGKWQHBNHJJPZ-LECWWXJVSA-N desonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O WBGKWQHBNHJJPZ-LECWWXJVSA-N 0.000 description 1
• 229960002593 desoximetasone Drugs 0.000 description 1
• VWVSBHGCDBMOOT-IIEHVVJPSA-N desoximetasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@H](C(=O)CO)[C@@]1(C)C[C@@H]2O VWVSBHGCDBMOOT-IIEHVVJPSA-N 0.000 description 1
• 238000001514 detection method Methods 0.000 description 1
• 238000011161 development Methods 0.000 description 1
• 230000018109 developmental process Effects 0.000 description 1
• 229960003957 dexamethasone Drugs 0.000 description 1
• UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 1
• 229960003657 dexamethasone acetate Drugs 0.000 description 1
• 229960000524 dexamethasone isonicotinate Drugs 0.000 description 1
• 229960004833 dexamethasone phosphate Drugs 0.000 description 1
• VQODGRNSFPNSQE-CXSFZGCWSA-N dexamethasone phosphate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)COP(O)(O)=O)(O)[C@@]1(C)C[C@@H]2O VQODGRNSFPNSQE-CXSFZGCWSA-N 0.000 description 1
• 208000033679 diabetic kidney disease Diseases 0.000 description 1
• NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
• 229940038472 dicalcium phosphate Drugs 0.000 description 1
• 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
• 229950009888 dichlorisone Drugs 0.000 description 1
• 235000014113 dietary fatty acids Nutrition 0.000 description 1
• 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
• 229960003970 diflucortolone valerate Drugs 0.000 description 1
• 229960004875 difluprednate Drugs 0.000 description 1
• 150000004683 dihydrates Chemical class 0.000 description 1
• NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 1
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
• GAFRWLVTHPVQGK-UHFFFAOYSA-N dipentyl sulfate Chemical compound CCCCCOS(=O)(=O)OCCCCC GAFRWLVTHPVQGK-UHFFFAOYSA-N 0.000 description 1
• 239000002270 dispersing agent Substances 0.000 description 1
• 239000006185 dispersion Substances 0.000 description 1
• 238000004090 dissolution Methods 0.000 description 1
• 238000009826 distribution Methods 0.000 description 1
• DLAHAXOYRFRPFQ-UHFFFAOYSA-N dodecyl benzoate Chemical compound CCCCCCCCCCCCOC(=O)C1=CC=CC=C1 DLAHAXOYRFRPFQ-UHFFFAOYSA-N 0.000 description 1
• 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
• 229940043264 dodecyl sulfate Drugs 0.000 description 1
• 239000002552 dosage form Substances 0.000 description 1
• 239000000428 dust Substances 0.000 description 1
• 239000003995 emulsifying agent Substances 0.000 description 1
• 210000001163 endosome Anatomy 0.000 description 1
• 239000007920 enema Substances 0.000 description 1
• 229940079360 enema for constipation Drugs 0.000 description 1
• 238000003912 environmental pollution Methods 0.000 description 1
• 230000002327 eosinophilic effect Effects 0.000 description 1
• 201000001564 eosinophilic gastroenteritis Diseases 0.000 description 1
• 210000002615 epidermis Anatomy 0.000 description 1
• 231100000321 erythema Toxicity 0.000 description 1
• CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical compound CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
• NFWQATGYWOTOHB-RISCZKNCSA-N ethyl (2s)-2-[[(1r)-1-(4-cyanophenyl)ethyl]amino]butanoate Chemical compound CCOC(=O)[C@H](CC)N[C@H](C)C1=CC=C(C#N)C=C1 NFWQATGYWOTOHB-RISCZKNCSA-N 0.000 description 1
• BFRLPRPEJGYMRQ-MFKMUULPSA-N ethyl (2s)-2-[[(1r)-1-[4-(n'-hydroxycarbamimidoyl)phenyl]ethyl]amino]butanoate Chemical compound CCOC(=O)[C@H](CC)N[C@H](C)C1=CC=C(C(N)=NO)C=C1 BFRLPRPEJGYMRQ-MFKMUULPSA-N 0.000 description 1
• CVLWFHIUGWCWJO-UHFFFAOYSA-N ethyl 2-[[3-fluoro-5-(n'-hydroxycarbamimidoyl)phenyl]methylamino]-4-methylpentanoate Chemical compound CCOC(=O)C(CC(C)C)NCC1=CC(F)=CC(C(N)=NO)=C1 CVLWFHIUGWCWJO-UHFFFAOYSA-N 0.000 description 1
• XIMFCGSNSKXPBO-UHFFFAOYSA-N ethyl 2-bromobutanoate Chemical compound CCOC(=O)C(Br)CC XIMFCGSNSKXPBO-UHFFFAOYSA-N 0.000 description 1
• 239000003889 eye drop Substances 0.000 description 1
• 229940012356 eye drops Drugs 0.000 description 1
• 229930195729 fatty acid Natural products 0.000 description 1
• 239000000194 fatty acid Substances 0.000 description 1
• 150000004665 fatty acids Chemical class 0.000 description 1
• 238000001914 filtration Methods 0.000 description 1
• 210000003811 finger Anatomy 0.000 description 1
• 239000005454 flavour additive Substances 0.000 description 1
• 229960003721 fluclorolone acetonide Drugs 0.000 description 1
• NJNWEGFJCGYWQT-VSXGLTOVSA-N fluclorolone acetonide Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(Cl)[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1Cl NJNWEGFJCGYWQT-VSXGLTOVSA-N 0.000 description 1
• SYWHXTATXSMDSB-GSLJADNHSA-N fludrocortisone acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)C)(O)[C@@]1(C)C[C@@H]2O SYWHXTATXSMDSB-GSLJADNHSA-N 0.000 description 1
• 229960004511 fludroxycortide Drugs 0.000 description 1
• JWRMHDSINXPDHB-OJAGFMMFSA-N flumethasone pivalate Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)COC(=O)C(C)(C)C)(O)[C@@]2(C)C[C@@H]1O JWRMHDSINXPDHB-OJAGFMMFSA-N 0.000 description 1
• 229940042902 flumethasone pivalate Drugs 0.000 description 1
• 229960000676 flunisolide Drugs 0.000 description 1
• 229960001347 fluocinolone acetonide Drugs 0.000 description 1
• FEBLZLNTKCEFIT-VSXGLTOVSA-N fluocinolone acetonide Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O FEBLZLNTKCEFIT-VSXGLTOVSA-N 0.000 description 1
• 229960000785 fluocinonide Drugs 0.000 description 1
• 229960003973 fluocortolone Drugs 0.000 description 1
• GAKMQHDJQHZUTJ-ULHLPKEOSA-N fluocortolone Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@@H](C)[C@H](C(=O)CO)[C@@]2(C)C[C@@H]1O GAKMQHDJQHZUTJ-ULHLPKEOSA-N 0.000 description 1
• 229960005283 fluocortolone pivalate Drugs 0.000 description 1
• XZBJVIQXJHGUBE-HZMVJJPJSA-N fluocortolone pivalate Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@@H](C)[C@H](C(=O)COC(=O)C(C)(C)C)[C@@]2(C)C[C@@H]1O XZBJVIQXJHGUBE-HZMVJJPJSA-N 0.000 description 1
• 229960003336 fluorocortisol acetate Drugs 0.000 description 1
• 229960001048 fluorometholone Drugs 0.000 description 1
• FAOZLTXFLGPHNG-KNAQIMQKSA-N fluorometholone Chemical compound C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@]2(F)[C@@H](O)C[C@]2(C)[C@@](O)(C(C)=O)CC[C@H]21 FAOZLTXFLGPHNG-KNAQIMQKSA-N 0.000 description 1
• DEFOZIFYUBUHHU-IYQKUMFPSA-N fluprednidene acetate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1CC(=C)[C@@](C(=O)COC(=O)C)(O)[C@@]1(C)C[C@@H]2O DEFOZIFYUBUHHU-IYQKUMFPSA-N 0.000 description 1
• 229960002650 fluprednidene acetate Drugs 0.000 description 1
• 229960000289 fluticasone propionate Drugs 0.000 description 1
• WMWTYOKRWGGJOA-CENSZEJFSA-N fluticasone propionate Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)SCF)(OC(=O)CC)[C@@]2(C)C[C@@H]1O WMWTYOKRWGGJOA-CENSZEJFSA-N 0.000 description 1
• 235000013355 food flavoring agent Nutrition 0.000 description 1
• 235000003599 food sweetener Nutrition 0.000 description 1
• 210000003194 forelimb Anatomy 0.000 description 1
• 238000002825 functional assay Methods 0.000 description 1
• 108020001507 fusion proteins Proteins 0.000 description 1
• 102000037865 fusion proteins Human genes 0.000 description 1
• DSLZVSRJTYRBFB-DUHBMQHGSA-N galactaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O DSLZVSRJTYRBFB-DUHBMQHGSA-N 0.000 description 1
• 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
• 239000007789 gas Substances 0.000 description 1
• 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
• SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 description 1
• 229960005277 gemcitabine Drugs 0.000 description 1
• 229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 1
• 230000008570 general process Effects 0.000 description 1
• 230000035784 germination Effects 0.000 description 1
• 210000004195 gingiva Anatomy 0.000 description 1
• 208000007565 gingivitis Diseases 0.000 description 1
• 229960002442 glucosamine Drugs 0.000 description 1
• 239000003292 glue Substances 0.000 description 1
• 229930195712 glutamate Natural products 0.000 description 1
• PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
• 229910052737 gold Inorganic materials 0.000 description 1
• 208000024908 graft versus host disease Diseases 0.000 description 1
• 239000005090 green fluorescent protein Substances 0.000 description 1
• 239000001963 growth medium Substances 0.000 description 1
• 229940093915 gynecological organic acid Drugs 0.000 description 1
• 230000003779 hair growth Effects 0.000 description 1
• 229960002383 halcinonide Drugs 0.000 description 1
• 150000008282 halocarbons Chemical class 0.000 description 1
• 229910052736 halogen Inorganic materials 0.000 description 1
• 125000001475 halogen functional group Chemical group 0.000 description 1
• 150000002367 halogens Chemical class 0.000 description 1
• 210000003958 hematopoietic stem cell Anatomy 0.000 description 1
• 206010019692 hepatic necrosis Diseases 0.000 description 1
• 208000006454 hepatitis Diseases 0.000 description 1
• 231100000283 hepatitis Toxicity 0.000 description 1
• MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
• 201000010884 herpes simplex virus keratitis Diseases 0.000 description 1
• FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
• 229960001340 histamine Drugs 0.000 description 1
• HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
• 210000005260 human cell Anatomy 0.000 description 1
• XGIHQYAWBCFNPY-AZOCGYLKSA-N hydrabamine Chemical compound C([C@@H]12)CC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC[C@@]1(C)CNCCNC[C@@]1(C)[C@@H]2CCC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC1 XGIHQYAWBCFNPY-AZOCGYLKSA-N 0.000 description 1
• 229960000890 hydrocortisone Drugs 0.000 description 1
• 229960001067 hydrocortisone acetate Drugs 0.000 description 1
• 229960001524 hydrocortisone butyrate Drugs 0.000 description 1
• 229950006240 hydrocortisone succinate Drugs 0.000 description 1
• 239000000017 hydrogel Substances 0.000 description 1
• 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
• 239000008309 hydrophilic cream Substances 0.000 description 1
• NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
• 230000003463 hyperproliferative effect Effects 0.000 description 1
• 201000002597 ichthyosis vulgaris Diseases 0.000 description 1
• JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 description 1
• 125000002883 imidazolyl group Chemical group 0.000 description 1
• 230000002519 immonomodulatory effect Effects 0.000 description 1
• 230000003053 immunization Effects 0.000 description 1
• 238000002649 immunization Methods 0.000 description 1
• 239000002955 immunomodulating agent Substances 0.000 description 1
• 239000003018 immunosuppressive agent Substances 0.000 description 1
• 229940125721 immunosuppressive agent Drugs 0.000 description 1
• 230000006872 improvement Effects 0.000 description 1
• 238000000099 in vitro assay Methods 0.000 description 1
• 238000001727 in vivo Methods 0.000 description 1
• 230000006698 induction Effects 0.000 description 1
• 230000002757 inflammatory effect Effects 0.000 description 1
• 208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
• 239000003999 initiator Substances 0.000 description 1
• 208000014674 injury Diseases 0.000 description 1
• 229910052500 inorganic mineral Inorganic materials 0.000 description 1
• 230000008611 intercellular interaction Effects 0.000 description 1
• 230000002452 interceptive effect Effects 0.000 description 1
• 229940079322 interferon Drugs 0.000 description 1
• 229940047124 interferons Drugs 0.000 description 1
• 201000006334 interstitial nephritis Diseases 0.000 description 1
• 230000003903 intestinal lesions Effects 0.000 description 1
• 238000001990 intravenous administration Methods 0.000 description 1
• 201000010659 intrinsic asthma Diseases 0.000 description 1
• 229910052742 iron Inorganic materials 0.000 description 1
• 208000012947 ischemia reperfusion injury Diseases 0.000 description 1
• 208000023569 ischemic bowel disease Diseases 0.000 description 1
• 230000000302 ischemic effect Effects 0.000 description 1
• KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
• 229960002725 isoflurane Drugs 0.000 description 1
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
• NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
• 201000010666 keratoconjunctivitis Diseases 0.000 description 1
• 229940001447 lactate Drugs 0.000 description 1
• 239000004310 lactic acid Substances 0.000 description 1
• 235000014655 lactic acid Nutrition 0.000 description 1
• 229940099584 lactobionate Drugs 0.000 description 1
• JYTUSYBCFIZPBE-AMTLMPIISA-N lactobionic acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O JYTUSYBCFIZPBE-AMTLMPIISA-N 0.000 description 1
• 229960000681 leflunomide Drugs 0.000 description 1
• VHOGYURTWQBHIL-UHFFFAOYSA-N leflunomide Chemical compound O1N=CC(C(=O)NC=2C=CC(=CC=2)C(F)(F)F)=C1C VHOGYURTWQBHIL-UHFFFAOYSA-N 0.000 description 1
• 201000010260 leiomyoma Diseases 0.000 description 1
• 230000003902 lesion Effects 0.000 description 1
• 208000032839 leukemia Diseases 0.000 description 1
• GWNVDXQDILPJIG-NXOLIXFESA-N leukotriene C4 Chemical compound CCCCC\C=C/C\C=C/C=C/C=C/[C@H]([C@@H](O)CCCC(O)=O)SC[C@@H](C(=O)NCC(O)=O)NC(=O)CC[C@H](N)C(O)=O GWNVDXQDILPJIG-NXOLIXFESA-N 0.000 description 1
• 201000011486 lichen planus Diseases 0.000 description 1
• 229960004194 lidocaine Drugs 0.000 description 1
• 208000027905 limb weakness Diseases 0.000 description 1
• 230000000670 limiting effect Effects 0.000 description 1
• 229910052744 lithium Inorganic materials 0.000 description 1
• 210000004185 liver Anatomy 0.000 description 1
• 231100000149 liver necrosis Toxicity 0.000 description 1
• 239000006210 lotion Substances 0.000 description 1
• 239000007937 lozenge Substances 0.000 description 1
• 210000004072 lung Anatomy 0.000 description 1
• 201000005202 lung cancer Diseases 0.000 description 1
• 208000020816 lung neoplasm Diseases 0.000 description 1
• 206010025135 lupus erythematosus Diseases 0.000 description 1
• 210000003563 lymphoid tissue Anatomy 0.000 description 1
• 231100001023 lymphopenia Toxicity 0.000 description 1
• 229960003646 lysine Drugs 0.000 description 1
• VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
• 239000000347 magnesium hydroxide Substances 0.000 description 1
• 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
• 235000009973 maize Nutrition 0.000 description 1
• 229940049920 malate Drugs 0.000 description 1
• 239000001630 malic acid Substances 0.000 description 1
• 235000011090 malic acid Nutrition 0.000 description 1
• 229960002510 mandelic acid Drugs 0.000 description 1
• 239000000594 mannitol Substances 0.000 description 1
• 235000010355 mannitol Nutrition 0.000 description 1
• 238000004519 manufacturing process Methods 0.000 description 1
• 238000001819 mass spectrum Methods 0.000 description 1
• 208000008585 mastocytosis Diseases 0.000 description 1
• HAWPXGHAZFHHAD-UHFFFAOYSA-N mechlorethamine Chemical compound ClCCN(C)CCCl HAWPXGHAZFHHAD-UHFFFAOYSA-N 0.000 description 1
• 229960004961 mechlorethamine Drugs 0.000 description 1
• 239000002609 medium Substances 0.000 description 1
• 231100001016 megaloblastic anemia Toxicity 0.000 description 1
• SGDBTWWWUNNDEQ-LBPRGKRZSA-N melphalan Chemical compound OC(=O)[C@@H](N)CC1=CC=C(N(CCCl)CCCl)C=C1 SGDBTWWWUNNDEQ-LBPRGKRZSA-N 0.000 description 1
• 229960001924 melphalan Drugs 0.000 description 1
• 239000001525 mentha piperita l. herb oil Substances 0.000 description 1
• 229960001810 meprednisone Drugs 0.000 description 1
• PIDANAQULIKBQS-RNUIGHNZSA-N meprednisone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)CC2=O PIDANAQULIKBQS-RNUIGHNZSA-N 0.000 description 1
• GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 description 1
• 229960001428 mercaptopurine Drugs 0.000 description 1
• 125000005341 metaphosphate group Chemical group 0.000 description 1
• 230000009401 metastasis Effects 0.000 description 1
• UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
• 229960000485 methotrexate Drugs 0.000 description 1
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
• QHCSUGVIKIXWAE-VQTJNVASSA-N methyl (2r)-2-[[(1s)-1-[4-[5-[3-(methoxymethyl)-4-(2-methylphenyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]amino]propanoate Chemical compound COCC1=CC(C=2ON=C(N=2)C=2C=CC(=CC=2)[C@H](C)N[C@H](C)C(=O)OC)=CC=C1C1=CC=CC=C1C QHCSUGVIKIXWAE-VQTJNVASSA-N 0.000 description 1
• BFJZMJAOSJIUMC-ZWKOTPCHSA-N methyl (2r)-2-[[(1s)-1-[4-[5-[3-methyl-4-[2-(trifluoromethyl)phenyl]phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]amino]propanoate Chemical compound C1=CC([C@H](C)N[C@H](C)C(=O)OC)=CC=C1C1=NOC(C=2C=C(C)C(=CC=2)C=2C(=CC=CC=2)C(F)(F)F)=N1 BFJZMJAOSJIUMC-ZWKOTPCHSA-N 0.000 description 1
• BFJZMJAOSJIUMC-ZVAWYAOSSA-N methyl (2s)-2-[1-[4-[5-[3-methyl-4-[2-(trifluoromethyl)phenyl]phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethylamino]propanoate Chemical compound C1=CC(C(C)N[C@@H](C)C(=O)OC)=CC=C1C1=NOC(C=2C=C(C)C(=CC=2)C=2C(=CC=CC=2)C(F)(F)F)=N1 BFJZMJAOSJIUMC-ZVAWYAOSSA-N 0.000 description 1
• LUVNJSXHNGHIPF-ZVAWYAOSSA-N methyl (2s)-2-[1-[4-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethylamino]propanoate Chemical compound C1=CC(C(C)N[C@@H](C)C(=O)OC)=CC=C1C1=NOC(C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=N1 LUVNJSXHNGHIPF-ZVAWYAOSSA-N 0.000 description 1
• RDBWYSWPXDSHOE-UHFFFAOYSA-N methyl 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate Chemical compound CC1=CC(C(=O)OC)=CC=C1B1OC(C)(C)C(C)(C)O1 RDBWYSWPXDSHOE-UHFFFAOYSA-N 0.000 description 1
• OJLOPKGSLYJEMD-URPKTTJQSA-N methyl 7-[(1r,2r,3r)-3-hydroxy-2-[(1e)-4-hydroxy-4-methyloct-1-en-1-yl]-5-oxocyclopentyl]heptanoate Chemical compound CCCCC(C)(O)C\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)OC OJLOPKGSLYJEMD-URPKTTJQSA-N 0.000 description 1
• 229940095102 methyl benzoate Drugs 0.000 description 1
• 229920000609 methyl cellulose Polymers 0.000 description 1
• KQSSATDQUYCRGS-UHFFFAOYSA-N methyl glycinate Chemical compound COC(=O)CN KQSSATDQUYCRGS-UHFFFAOYSA-N 0.000 description 1
• NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical class [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 1
• 239000001923 methylcellulose Substances 0.000 description 1
• 235000010981 methylcellulose Nutrition 0.000 description 1
• 229960004584 methylprednisolone Drugs 0.000 description 1
• 229960001293 methylprednisolone acetate Drugs 0.000 description 1
• IMBXEJJVJRTNOW-XYMSELFBSA-N methylprednisolone succinate Chemical compound C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)[C@@](O)(C(=O)COC(=O)CCC(O)=O)CC[C@H]21 IMBXEJJVJRTNOW-XYMSELFBSA-N 0.000 description 1
• 229950009831 methylprednisolone succinate Drugs 0.000 description 1
• 239000003094 microcapsule Substances 0.000 description 1
• 239000008108 microcrystalline cellulose Substances 0.000 description 1
• 229940016286 microcrystalline cellulose Drugs 0.000 description 1
• 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
• 206010027599 migraine Diseases 0.000 description 1
• 235000010755 mineral Nutrition 0.000 description 1
• 239000011707 mineral Substances 0.000 description 1
• 239000002480 mineral oil Substances 0.000 description 1
• 235000010446 mineral oil Nutrition 0.000 description 1
• 229960005249 misoprostol Drugs 0.000 description 1
• 239000011259 mixed solution Substances 0.000 description 1
• 229950000844 mizoribine Drugs 0.000 description 1
• 150000004682 monohydrates Chemical class 0.000 description 1
• 208000013734 mononeuritis simplex Diseases 0.000 description 1
• 201000005518 mononeuropathy Diseases 0.000 description 1
• 239000002324 mouth wash Substances 0.000 description 1
• 229960003816 muromonab-cd3 Drugs 0.000 description 1
• 210000003205 muscle Anatomy 0.000 description 1
• 201000006938 muscular dystrophy Diseases 0.000 description 1
• 206010028417 myasthenia gravis Diseases 0.000 description 1
• 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• UWBOIAUVONKWLK-UHFFFAOYSA-N n-[[2-fluoro-4-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]-1-hydroxy-n-methyl-1-oxopropan-2-amine oxide Chemical compound C1=C(F)C(C[N+](C)([O-])C(C(O)=O)C)=CC=C1C1=NOC(C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=N1 UWBOIAUVONKWLK-UHFFFAOYSA-N 0.000 description 1
• TUSOEQPDGLCXBS-UHFFFAOYSA-N n-methyl-1-[3-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]methanamine Chemical compound CNCC1=CC=CC(C=2N=C(ON=2)C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=C1 TUSOEQPDGLCXBS-UHFFFAOYSA-N 0.000 description 1
• YIPKJMBODMDMJQ-UHFFFAOYSA-N n-methyl-1-[4-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethanamine Chemical compound C1=CC(C(C)NC)=CC=C1C1=NOC(C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=N1 YIPKJMBODMDMJQ-UHFFFAOYSA-N 0.000 description 1
• KVBGVZZKJNLNJU-UHFFFAOYSA-M naphthalene-2-sulfonate Chemical compound C1=CC=CC2=CC(S(=O)(=O)[O-])=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-M 0.000 description 1
• 229940100662 nasal drops Drugs 0.000 description 1
• 229940097496 nasal spray Drugs 0.000 description 1
• 239000007922 nasal spray Substances 0.000 description 1
• 229920003052 natural elastomer Polymers 0.000 description 1
• 229920001194 natural rubber Polymers 0.000 description 1
• 235000021096 natural sweeteners Nutrition 0.000 description 1
• 230000017074 necrotic cell death Effects 0.000 description 1
• 208000004995 necrotizing enterocolitis Diseases 0.000 description 1
• 210000000440 neutrophil Anatomy 0.000 description 1
• 235000001968 nicotinic acid Nutrition 0.000 description 1
• 239000011664 nicotinic acid Substances 0.000 description 1
• 229910000510 noble metal Inorganic materials 0.000 description 1
• 230000000414 obstructive effect Effects 0.000 description 1
• OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
• WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
• 235000005985 organic acids Nutrition 0.000 description 1
• 150000007530 organic bases Chemical class 0.000 description 1
• 150000002905 orthoesters Chemical class 0.000 description 1
• 238000007254 oxidation reaction Methods 0.000 description 1
• 230000001590 oxidative effect Effects 0.000 description 1
• 239000001301 oxygen Substances 0.000 description 1
• 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 1
• 229910052763 palladium Inorganic materials 0.000 description 1
• JGBZTJWQMWZVNX-UHFFFAOYSA-N palladium;tricyclohexylphosphane Chemical compound [Pd].C1CCCCC1P(C1CCCCC1)C1CCCCC1.C1CCCCC1P(C1CCCCC1)C1CCCCC1 JGBZTJWQMWZVNX-UHFFFAOYSA-N 0.000 description 1
• 239000012188 paraffin wax Substances 0.000 description 1
• 229960000865 paramethasone acetate Drugs 0.000 description 1
• 238000007911 parenteral administration Methods 0.000 description 1
• 239000002245 particle Substances 0.000 description 1
• 239000011236 particulate material Substances 0.000 description 1
• 235000010603 pastilles Nutrition 0.000 description 1
• 239000008188 pellet Substances 0.000 description 1
• 229940049954 penicillin Drugs 0.000 description 1
• RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
• 235000019477 peppermint oil Nutrition 0.000 description 1
• 201000006195 perinatal necrotizing enterocolitis Diseases 0.000 description 1
• 201000001245 periodontitis Diseases 0.000 description 1
• 210000004261 periodontium Anatomy 0.000 description 1
• JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
• 229940124531 pharmaceutical excipient Drugs 0.000 description 1
• 230000003285 pharmacodynamic effect Effects 0.000 description 1
• 239000012071 phase Substances 0.000 description 1
• 229940049953 phenylacetate Drugs 0.000 description 1
• WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
• 150000008105 phosphatidylcholines Chemical class 0.000 description 1
• 150000003904 phospholipids 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
• 229950010765 pivalate Drugs 0.000 description 1
• IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
• 239000011505 plaster Substances 0.000 description 1
• 229920000747 poly(lactic acid) Polymers 0.000 description 1
• 229920000768 polyamine Polymers 0.000 description 1
• 201000006292 polyarteritis nodosa Diseases 0.000 description 1
• 229920001610 polycaprolactone Polymers 0.000 description 1
• 229920002721 polycyanoacrylate Polymers 0.000 description 1
• 239000004626 polylactic acid Substances 0.000 description 1
• 229920000656 polylysine Polymers 0.000 description 1
• 208000005987 polymyositis Diseases 0.000 description 1
• 208000019629 polyneuritis Diseases 0.000 description 1
• 229920006324 polyoxymethylene Polymers 0.000 description 1
• 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
• CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
• 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
• 229960001297 prednazoline Drugs 0.000 description 1
• 229960005205 prednisolone Drugs 0.000 description 1
• OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 1
• 229960002800 prednisolone acetate Drugs 0.000 description 1
• 229960004786 prednisolone phosphate Drugs 0.000 description 1
• JDOZJEUDSLGTLU-VWUMJDOOSA-N prednisolone phosphate Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)COP(O)(O)=O)[C@@H]4[C@@H]3CCC2=C1 JDOZJEUDSLGTLU-VWUMJDOOSA-N 0.000 description 1
• WVKSUFYQOHQCMM-YGZHYJPASA-N prednisolone sulfobenzoate Chemical compound O=C([C@@]1(O)CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)[C@@H](O)C[C@@]21C)COC(=O)C1=CC=CC(S(O)(=O)=O)=C1 WVKSUFYQOHQCMM-YGZHYJPASA-N 0.000 description 1
• 229950004954 prednisolone sulfobenzoate Drugs 0.000 description 1
• 229960004618 prednisone Drugs 0.000 description 1
• XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
• 229960001917 prednylidene Drugs 0.000 description 1
• WSVOMANDJDYYEY-CWNVBEKCSA-N prednylidene Chemical group O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](C(=C)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 WSVOMANDJDYYEY-CWNVBEKCSA-N 0.000 description 1
• 238000004321 preservation Methods 0.000 description 1
• 230000002335 preservative effect Effects 0.000 description 1
• 230000002265 prevention Effects 0.000 description 1
• 208000025638 primary cutaneous T-cell non-Hodgkin lymphoma Diseases 0.000 description 1
• 108090000765 processed proteins & peptides Proteins 0.000 description 1
• 230000035755 proliferation Effects 0.000 description 1
• 230000001737 promoting effect Effects 0.000 description 1
• 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
• 239000011241 protective layer Substances 0.000 description 1
• 239000003586 protic polar solvent Substances 0.000 description 1
• 150000003212 purines Chemical class 0.000 description 1
• MIXMJCQRHVAJIO-TZHJZOAOSA-N qk4dys664x Chemical compound O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O MIXMJCQRHVAJIO-TZHJZOAOSA-N 0.000 description 1
• 238000010791 quenching Methods 0.000 description 1
• 230000005855 radiation Effects 0.000 description 1
• 239000000376 reactant Substances 0.000 description 1
• 230000035484 reaction time Effects 0.000 description 1
• 239000000018 receptor agonist Substances 0.000 description 1
• 229940044601 receptor agonist Drugs 0.000 description 1
• 238000001525 receptor binding assay Methods 0.000 description 1
• 238000001953 recrystallisation Methods 0.000 description 1
• 238000005932 reductive alkylation reaction Methods 0.000 description 1
• 238000011160 research Methods 0.000 description 1
• 238000002271 resection Methods 0.000 description 1
• 208000023504 respiratory system disease Diseases 0.000 description 1
• 230000002441 reversible effect Effects 0.000 description 1
• 201000003068 rheumatic fever Diseases 0.000 description 1
• 206010039083 rhinitis Diseases 0.000 description 1
• 101150024819 s1pr1 gene Proteins 0.000 description 1
• 101150079914 s1pr2 gene Proteins 0.000 description 1
• 235000019204 saccharin Nutrition 0.000 description 1
• CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
• 229940081974 saccharin Drugs 0.000 description 1
• 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
• YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
• 229960001860 salicylate Drugs 0.000 description 1
• MOODSJOROWROTO-UHFFFAOYSA-N salicylsulfuric acid Chemical compound OC(=O)C1=CC=CC=C1OS(O)(=O)=O MOODSJOROWROTO-UHFFFAOYSA-N 0.000 description 1
• 230000037390 scarring Effects 0.000 description 1
• 230000007017 scission Effects 0.000 description 1
• 208000010157 sclerosing cholangitis Diseases 0.000 description 1
• 238000007789 sealing Methods 0.000 description 1
• 208000008742 seborrheic dermatitis Diseases 0.000 description 1
• 239000002412 selectin antagonist Substances 0.000 description 1
• 230000035945 sensitivity Effects 0.000 description 1
• 230000009919 sequestration Effects 0.000 description 1
• 210000002966 serum Anatomy 0.000 description 1
• 239000012679 serum free medium Substances 0.000 description 1
• 239000004208 shellac Substances 0.000 description 1
• 229940113147 shellac Drugs 0.000 description 1
• ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
• 235000013874 shellac Nutrition 0.000 description 1
• 230000035939 shock Effects 0.000 description 1
• 208000004003 siderosis Diseases 0.000 description 1
• 230000019491 signal transduction Effects 0.000 description 1
• RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
• 235000012239 silicon dioxide Nutrition 0.000 description 1
• 229910052814 silicon oxide Inorganic materials 0.000 description 1
• 210000003491 skin Anatomy 0.000 description 1
• 208000017520 skin disease Diseases 0.000 description 1
• AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
• 239000001632 sodium acetate Substances 0.000 description 1
• 235000017281 sodium acetate Nutrition 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
• 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
• HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
• 235000019254 sodium formate Nutrition 0.000 description 1
• SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
• RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
• 239000001488 sodium phosphate Substances 0.000 description 1
• 229910000162 sodium phosphate Inorganic materials 0.000 description 1
• 239000011877 solvent mixture Substances 0.000 description 1
• 238000003797 solvolysis reaction Methods 0.000 description 1
• 239000000600 sorbitol Substances 0.000 description 1
• 150000003408 sphingolipids Chemical class 0.000 description 1
• 239000008117 stearic acid Substances 0.000 description 1
• 229960005322 streptomycin Drugs 0.000 description 1
• 238000010254 subcutaneous injection Methods 0.000 description 1
• 239000007929 subcutaneous injection Substances 0.000 description 1
• 125000001424 substituent group Chemical group 0.000 description 1
• 125000000547 substituted alkyl group Chemical group 0.000 description 1
• 125000003107 substituted aryl group Chemical group 0.000 description 1
• 229940086735 succinate Drugs 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
• 229960002317 succinimide Drugs 0.000 description 1
• 125000001010 sulfinic acid amide group Chemical group 0.000 description 1
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
• BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
• 229940071103 sulfosalicylate Drugs 0.000 description 1
• 239000006228 supernatant Substances 0.000 description 1
• 239000000829 suppository Substances 0.000 description 1
• 230000004083 survival effect Effects 0.000 description 1
• 239000003765 sweetening agent Substances 0.000 description 1
• 208000011580 syndromic disease Diseases 0.000 description 1
• 229920003051 synthetic elastomer Polymers 0.000 description 1
• 238000010189 synthetic method Methods 0.000 description 1
• 239000005061 synthetic rubber Substances 0.000 description 1
• 235000002906 tartaric acid Nutrition 0.000 description 1
• 239000011975 tartaric acid Substances 0.000 description 1
• 229960000331 teriflunomide Drugs 0.000 description 1
• UTNUDOFZCWSZMS-YFHOEESVSA-N teriflunomide Chemical compound C\C(O)=C(/C#N)C(=O)NC1=CC=C(C(F)(F)F)C=C1 UTNUDOFZCWSZMS-YFHOEESVSA-N 0.000 description 1
• CESUXLKAADQNTB-UHFFFAOYSA-N tert-butanesulfinamide Chemical group CC(C)(C)S(N)=O CESUXLKAADQNTB-UHFFFAOYSA-N 0.000 description 1
• VZGOTMQIYKUGHD-ICCFGIFFSA-N tert-butyl (2r)-2-[[2-hydroxy-1-[4-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]amino]propanoate Chemical compound C1=CC(C(CO)N[C@H](C)C(=O)OC(C)(C)C)=CC=C1C1=NOC(C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=N1 VZGOTMQIYKUGHD-ICCFGIFFSA-N 0.000 description 1
• TZHVYFBSLOMRCU-RXMQYKEDSA-N tert-butyl (2r)-2-aminopropanoate Chemical compound C[C@@H](N)C(=O)OC(C)(C)C TZHVYFBSLOMRCU-RXMQYKEDSA-N 0.000 description 1
• VBPUOTMXVZMINS-NDEPHWFRSA-N tert-butyl (2s)-2-[[2-fluoro-4-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl-methylamino]-3-methylbutanoate Chemical compound C1=C(F)C(CN(C)[C@@H](C(C)C)C(=O)OC(C)(C)C)=CC=C1C1=NOC(C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=N1 VBPUOTMXVZMINS-NDEPHWFRSA-N 0.000 description 1
• WGAZJKFEKPJBKC-IBGZPJMESA-N tert-butyl (2s)-2-[[2-fluoro-4-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl-methylamino]propanoate Chemical compound C1=C(F)C(CN(C)[C@@H](C)C(=O)OC(C)(C)C)=CC=C1C1=NOC(C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=N1 WGAZJKFEKPJBKC-IBGZPJMESA-N 0.000 description 1
• NJZNMEISFFPUKW-MHZLTWQESA-N tert-butyl (2s)-2-[[2-fluoro-4-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]methylamino]-3-methylbutanoate Chemical compound C1=C(F)C(CN[C@@H](C(C)C)C(=O)OC(C)(C)C)=CC=C1C1=NOC(C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=N1 NJZNMEISFFPUKW-MHZLTWQESA-N 0.000 description 1
• RDWZQVGVBTYCBD-QRPNPIFTSA-N tert-butyl (2s)-2-amino-3-[(2-methylpropan-2-yl)oxy]propanoate;hydrochloride Chemical compound Cl.CC(C)(C)OC[C@H](N)C(=O)OC(C)(C)C RDWZQVGVBTYCBD-QRPNPIFTSA-N 0.000 description 1
• RJBVJBGFJIHJSZ-ZETCQYMHSA-N tert-butyl (2s)-2-amino-3-methylbutanoate Chemical compound CC(C)[C@H](N)C(=O)OC(C)(C)C RJBVJBGFJIHJSZ-ZETCQYMHSA-N 0.000 description 1
• TZHVYFBSLOMRCU-YFKPBYRVSA-N tert-butyl (2s)-2-aminopropanoate Chemical compound C[C@H](N)C(=O)OC(C)(C)C TZHVYFBSLOMRCU-YFKPBYRVSA-N 0.000 description 1
• RNLQHMIDSCYLAK-UHFFFAOYSA-N tert-butyl 2-(methylamino)acetate;hydron;chloride Chemical compound Cl.CNCC(=O)OC(C)(C)C RNLQHMIDSCYLAK-UHFFFAOYSA-N 0.000 description 1
• PRYVBGSLLFOVKD-UHFFFAOYSA-N tert-butyl 2-[1-(4-cyanophenyl)ethylamino]acetate Chemical compound CC(C)(C)OC(=O)CNC(C)C1=CC=C(C#N)C=C1 PRYVBGSLLFOVKD-UHFFFAOYSA-N 0.000 description 1
• NGCUUWDYTRAPBS-UHFFFAOYSA-N tert-butyl 2-[1-(4-cyanophenyl)ethylideneamino]acetate Chemical compound CC(C)(C)OC(=O)CN=C(C)C1=CC=C(C#N)C=C1 NGCUUWDYTRAPBS-UHFFFAOYSA-N 0.000 description 1
• HDPPMKBCLPLGSA-UHFFFAOYSA-N tert-butyl 2-[1-[3-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethylamino]acetate Chemical compound CC(C)(C)OC(=O)CNC(C)C1=CC=CC(C=2N=C(ON=2)C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=C1 HDPPMKBCLPLGSA-UHFFFAOYSA-N 0.000 description 1
• GLUHDPMWJAZWFL-UHFFFAOYSA-N tert-butyl 2-[1-[4-[5-[3-methyl-4-[2-(trifluoromethyl)phenyl]phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethylamino]acetate Chemical compound C1=CC(C(NCC(=O)OC(C)(C)C)C)=CC=C1C1=NOC(C=2C=C(C)C(=CC=2)C=2C(=CC=CC=2)C(F)(F)F)=N1 GLUHDPMWJAZWFL-UHFFFAOYSA-N 0.000 description 1
• ASVNMTTVOCQYBL-UHFFFAOYSA-N tert-butyl 2-[1-[4-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethylamino]acetate Chemical compound C1=CC(C(NCC(=O)OC(C)(C)C)C)=CC=C1C1=NOC(C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=N1 ASVNMTTVOCQYBL-UHFFFAOYSA-N 0.000 description 1
• GLUHDPMWJAZWFL-LJQANCHMSA-N tert-butyl 2-[[(1r)-1-[4-[5-[3-methyl-4-[2-(trifluoromethyl)phenyl]phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]amino]acetate Chemical compound C1=CC([C@H](NCC(=O)OC(C)(C)C)C)=CC=C1C1=NOC(C=2C=C(C)C(=CC=2)C=2C(=CC=CC=2)C(F)(F)F)=N1 GLUHDPMWJAZWFL-LJQANCHMSA-N 0.000 description 1
• PRYVBGSLLFOVKD-NSHDSACASA-N tert-butyl 2-[[(1s)-1-(4-cyanophenyl)ethyl]amino]acetate Chemical compound CC(C)(C)OC(=O)CN[C@@H](C)C1=CC=C(C#N)C=C1 PRYVBGSLLFOVKD-NSHDSACASA-N 0.000 description 1
• VJDIQWCOTKQWAX-QFIPXVFZSA-N tert-butyl 2-[[(1s)-1-[4-[5-[3-(methoxymethyl)-4-(2-methylphenyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]-methylamino]acetate Chemical compound COCC1=CC(C=2ON=C(N=2)C=2C=CC(=CC=2)[C@H](C)N(C)CC(=O)OC(C)(C)C)=CC=C1C1=CC=CC=C1C VJDIQWCOTKQWAX-QFIPXVFZSA-N 0.000 description 1
• NHBPSYQMGAOZGG-NRFANRHFSA-N tert-butyl 2-[[(1s)-1-[4-[5-[3-(methoxymethyl)-4-(2-methylphenyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]amino]acetate Chemical compound COCC1=CC(C=2ON=C(N=2)C=2C=CC(=CC=2)[C@H](C)NCC(=O)OC(C)(C)C)=CC=C1C1=CC=CC=C1C NHBPSYQMGAOZGG-NRFANRHFSA-N 0.000 description 1
• IRWHVDULFBOCFB-UHFFFAOYSA-N tert-butyl 2-[[2-fluoro-4-[(z)-n'-hydroxycarbamimidoyl]phenyl]methylamino]butanoate Chemical compound CC(C)(C)OC(=O)C(CC)NCC1=CC=C(C(N)=NO)C=C1F IRWHVDULFBOCFB-UHFFFAOYSA-N 0.000 description 1
• BXRKLBUUNUWKCJ-UHFFFAOYSA-N tert-butyl 2-[[2-fluoro-4-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl-methylamino]butanoate Chemical compound C1=C(F)C(CN(C)C(CC)C(=O)OC(C)(C)C)=CC=C1C1=NOC(C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=N1 BXRKLBUUNUWKCJ-UHFFFAOYSA-N 0.000 description 1
• PFQFSUPSJDRXSD-UHFFFAOYSA-N tert-butyl 2-[[2-hydroxy-1-[4-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]amino]acetate Chemical compound CC1=CC=CC=C1C1=CC=C(C=2ON=C(N=2)C=2C=CC(=CC=2)C(CO)NCC(=O)OC(C)(C)C)C=C1C(F)(F)F PFQFSUPSJDRXSD-UHFFFAOYSA-N 0.000 description 1
• WUEJRAVQKAPIFZ-UHFFFAOYSA-N tert-butyl 2-[[2-methoxy-1-[4-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]-methylamino]acetate Chemical compound C1=CC(C(N(C)CC(=O)OC(C)(C)C)COC)=CC=C1C1=NOC(C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=N1 WUEJRAVQKAPIFZ-UHFFFAOYSA-N 0.000 description 1
• ALMFAYCILDGDLO-UHFFFAOYSA-N tert-butyl 2-[[3-fluoro-5-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]methylamino]-2-methylpropanoate Chemical compound CC1=CC=CC=C1C1=CC=C(C=2ON=C(N=2)C=2C=C(CNC(C)(C)C(=O)OC(C)(C)C)C=C(F)C=2)C=C1C(F)(F)F ALMFAYCILDGDLO-UHFFFAOYSA-N 0.000 description 1
• PCJZLBINENSRIC-HXUWFJFHSA-N tert-butyl 2-[methyl-[(1r)-1-[4-[5-[3-methyl-4-[2-(trifluoromethyl)phenyl]phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]amino]acetate Chemical compound C1=CC([C@H](N(C)CC(=O)OC(C)(C)C)C)=CC=C1C1=NOC(C=2C=C(C)C(=CC=2)C=2C(=CC=CC=2)C(F)(F)F)=N1 PCJZLBINENSRIC-HXUWFJFHSA-N 0.000 description 1
• CMJRINJXEXYIJF-HXUWFJFHSA-N tert-butyl 2-[methyl-[(1r)-1-[4-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]amino]acetate Chemical compound C1=CC([C@H](N(C)CC(=O)OC(C)(C)C)C)=CC=C1C1=NOC(C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=N1 CMJRINJXEXYIJF-HXUWFJFHSA-N 0.000 description 1
• PCJZLBINENSRIC-FQEVSTJZSA-N tert-butyl 2-[methyl-[(1s)-1-[4-[5-[3-methyl-4-[2-(trifluoromethyl)phenyl]phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]amino]acetate Chemical compound C1=CC([C@@H](N(C)CC(=O)OC(C)(C)C)C)=CC=C1C1=NOC(C=2C=C(C)C(=CC=2)C=2C(=CC=CC=2)C(F)(F)F)=N1 PCJZLBINENSRIC-FQEVSTJZSA-N 0.000 description 1
• CMJRINJXEXYIJF-FQEVSTJZSA-N tert-butyl 2-[methyl-[(1s)-1-[4-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]amino]acetate Chemical compound C1=CC([C@@H](N(C)CC(=O)OC(C)(C)C)C)=CC=C1C1=NOC(C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=N1 CMJRINJXEXYIJF-FQEVSTJZSA-N 0.000 description 1
• PCJZLBINENSRIC-UHFFFAOYSA-N tert-butyl 2-[methyl-[1-[4-[5-[3-methyl-4-[2-(trifluoromethyl)phenyl]phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]amino]acetate Chemical compound C1=CC(C(N(C)CC(=O)OC(C)(C)C)C)=CC=C1C1=NOC(C=2C=C(C)C(=CC=2)C=2C(=CC=CC=2)C(F)(F)F)=N1 PCJZLBINENSRIC-UHFFFAOYSA-N 0.000 description 1
• CVAWKJKISIPBOD-UHFFFAOYSA-N tert-butyl 2-bromopropanoate Chemical compound CC(Br)C(=O)OC(C)(C)C CVAWKJKISIPBOD-UHFFFAOYSA-N 0.000 description 1
• HKSMZGUHWNXSHU-UHFFFAOYSA-N tert-butyl N-[1-[4-[5-[3-methyl-4-[2-(trifluoromethyl)phenyl]phenyl]-1,2,4-oxadiazol-3-yl]phenyl]ethyl]carbamate Chemical compound C1=CC(C(NC(=O)OC(C)(C)C)C)=CC=C1C1=NOC(C=2C=C(C)C(=CC=2)C=2C(=CC=CC=2)C(F)(F)F)=N1 HKSMZGUHWNXSHU-UHFFFAOYSA-N 0.000 description 1
• ZTQJWLXLROSEQG-UHFFFAOYSA-N tert-butyl N-[2-[3-(N'-hydroxycarbamimidoyl)phenyl]ethyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCC1=CC=CC(C(N)=NO)=C1 ZTQJWLXLROSEQG-UHFFFAOYSA-N 0.000 description 1
• WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
• NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 description 1
• SUOSOBLQTPQGEB-SECBINFHSA-N tert-butyl n-[(1r)-1-[4-(n'-hydroxycarbamimidoyl)phenyl]ethyl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@H](C)C1=CC=C(C(N)=NO)C=C1 SUOSOBLQTPQGEB-SECBINFHSA-N 0.000 description 1
• SYCYTDVODOGBBU-UHFFFAOYSA-N tert-butyl n-[1-(4-cyanophenyl)ethyl]carbamate Chemical compound CC(C)(C)OC(=O)NC(C)C1=CC=C(C#N)C=C1 SYCYTDVODOGBBU-UHFFFAOYSA-N 0.000 description 1
• OXVHRQADRJDMPT-UHFFFAOYSA-N tert-butyl n-methyl-n-[[3-[5-[4-(2-methylphenyl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]carbamate Chemical compound CC(C)(C)OC(=O)N(C)CC1=CC=CC(C=2N=C(ON=2)C=2C=C(C(C=3C(=CC=CC=3)C)=CC=2)C(F)(F)F)=C1 OXVHRQADRJDMPT-UHFFFAOYSA-N 0.000 description 1
• 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 150000003512 tertiary amines Chemical class 0.000 description 1
• 229960003433 thalidomide Drugs 0.000 description 1
• 229960004559 theobromine Drugs 0.000 description 1
• 238000002560 therapeutic procedure Methods 0.000 description 1
• 230000036575 thermal burns Effects 0.000 description 1
• 238000001149 thermolysis Methods 0.000 description 1
• 239000002562 thickening agent Substances 0.000 description 1
• 238000004809 thin layer chromatography Methods 0.000 description 1
• 229960001196 thiotepa Drugs 0.000 description 1
• FYOWZTWVYZOZSI-UHFFFAOYSA-N thiourea dioxide Chemical compound NC(=N)S(O)=O FYOWZTWVYZOZSI-UHFFFAOYSA-N 0.000 description 1
• 210000003813 thumb Anatomy 0.000 description 1
• JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium ethoxide Chemical compound [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 description 1
• BISFDZNIUZIKJD-XDANTLIUSA-N tixocortol pivalate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)CSC(=O)C(C)(C)C)(O)[C@@]1(C)C[C@@H]2O BISFDZNIUZIKJD-XDANTLIUSA-N 0.000 description 1
• 229960003114 tixocortol pivalate Drugs 0.000 description 1
• 125000003944 tolyl group Chemical group 0.000 description 1
• 238000011200 topical administration Methods 0.000 description 1
• 229940100611 topical cream Drugs 0.000 description 1
• 229940100615 topical ointment Drugs 0.000 description 1
• 239000003053 toxin Substances 0.000 description 1
• 231100000765 toxin 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
• WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
• 230000032258 transport Effects 0.000 description 1
• 230000008733 trauma Effects 0.000 description 1
• 229960005294 triamcinolone Drugs 0.000 description 1
• GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 description 1
• GUYPYYARYIIWJZ-CYEPYHPTSA-N triamcinolone benetonide Chemical compound O=C([C@]12[C@H](OC(C)(C)O1)C[C@@H]1[C@@]2(C[C@H](O)[C@]2(F)[C@@]3(C)C=CC(=O)C=C3CC[C@H]21)C)COC(=O)C(C)CNC(=O)C1=CC=CC=C1 GUYPYYARYIIWJZ-CYEPYHPTSA-N 0.000 description 1
• 229950006782 triamcinolone benetonide Drugs 0.000 description 1
• 229960004320 triamcinolone diacetate Drugs 0.000 description 1
• 229960004221 triamcinolone hexacetonide Drugs 0.000 description 1
• YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
• ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
• WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical group [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 description 1
• YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
• RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
• 229940056345 tums Drugs 0.000 description 1
• 238000004704 ultra performance liquid chromatography Methods 0.000 description 1
• 238000001946 ultra-performance liquid chromatography-mass spectrometry Methods 0.000 description 1
• 210000002700 urine Anatomy 0.000 description 1
• 230000003966 vascular damage Effects 0.000 description 1
• 201000005539 vernal conjunctivitis Diseases 0.000 description 1
• 201000001862 viral hepatitis Diseases 0.000 description 1
• 239000008215 water for injection Substances 0.000 description 1
• 238000005303 weighing Methods 0.000 description 1
• 238000009736 wetting Methods 0.000 description 1
• 229930195724 β-lactose Natural products 0.000 description 1