CZ303312B6 - Deriváty karboxylové kyseliny, které inhibují vazbu integrinu na jejich receptory - Google Patents

Info

Publication number

CZ303312B6

CZ303312B6 CZ20013963A CZ20013963A CZ303312B6 CZ 303312 B6 CZ303312 B6 CZ 303312B6 CZ 20013963 A CZ20013963 A CZ 20013963A CZ 20013963 A CZ20013963 A CZ 20013963A CZ 303312 B6 CZ303312 B6 CZ 303312B6

Authority

CZ

Czechia

Prior art keywords

amino

methyl

dihydro

alkyl

carbonyl

Prior art date

1999-05-07

Links

• Espacenet
• Global Dossier
• Discuss

• 102000006495 integrins Human genes 0.000 title claims abstract description 19
• 150000001732 carboxylic acid derivatives Chemical class 0.000 title claims abstract description 5
• 230000002401 inhibitory effect Effects 0.000 title claims description 9
• 102000005962 receptors Human genes 0.000 title abstract description 4
• 108020003175 receptors Proteins 0.000 title abstract description 4
• 108010044426 integrins Proteins 0.000 claims abstract description 18
• -1 cyano, carboxy Chemical group 0.000 claims description 537
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 427
• KRZJRNZICWNMOA-GXSJLCMTSA-N (3s,4r)-4,8-dihydroxy-3-methoxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1=CC=C2[C@@H](O)[C@@H](OC)CC(=O)C2=C1O KRZJRNZICWNMOA-GXSJLCMTSA-N 0.000 claims description 274
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 174
• 150000001875 compounds Chemical class 0.000 claims description 169
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 122
• 125000000217 alkyl group Chemical group 0.000 claims description 95
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 90
• 235000019260 propionic acid Nutrition 0.000 claims description 83
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 82
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 71
• 125000003118 aryl group Chemical group 0.000 claims description 70
• 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 claims description 65
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 59
• 125000000623 heterocyclic group Chemical group 0.000 claims description 51
• 229910052739 hydrogen Inorganic materials 0.000 claims description 45
• 239000001257 hydrogen Substances 0.000 claims description 44
• 229920006395 saturated elastomer Polymers 0.000 claims description 41
• 125000003342 alkenyl group Chemical group 0.000 claims description 40
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 37
• 125000000304 alkynyl group Chemical group 0.000 claims description 36
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 35
• 125000003545 alkoxy group Chemical group 0.000 claims description 34
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 31
• 229910052757 nitrogen Inorganic materials 0.000 claims description 30
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
• 125000001424 substituent group Chemical group 0.000 claims description 29
• 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 26
• 125000003282 alkyl amino group Chemical group 0.000 claims description 26
• 150000003857 carboxamides Chemical class 0.000 claims description 26
• 125000001188 haloalkyl group Chemical group 0.000 claims description 26
• 150000002367 halogens Chemical class 0.000 claims description 26
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 25
• 229910052736 halogen Inorganic materials 0.000 claims description 25
• MBVFRSJFKMJRHA-UHFFFAOYSA-N 4-fluoro-1-benzofuran-7-carbaldehyde Chemical compound FC1=CC=C(C=O)C2=C1C=CO2 MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 claims description 24
• 125000004986 diarylamino group Chemical group 0.000 claims description 24
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 24
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 23
• 125000003435 aroyl group Chemical group 0.000 claims description 23
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 23
• 239000002253 acid Substances 0.000 claims description 22
• 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 22
• 125000004104 aryloxy group Chemical group 0.000 claims description 22
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 22
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 22
• 150000003839 salts Chemical class 0.000 claims description 22
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 21
• 125000001769 aryl amino group Chemical group 0.000 claims description 21
• 229910052799 carbon Inorganic materials 0.000 claims description 21
• 125000005000 thioaryl group Chemical group 0.000 claims description 21
• 229910052760 oxygen Inorganic materials 0.000 claims description 19
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 18
• 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 17
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 16
• 125000005309 thioalkoxy group Chemical group 0.000 claims description 16
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 15
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
• 125000006323 alkenyl amino group Chemical group 0.000 claims description 13
• 239000003814 drug Substances 0.000 claims description 13
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 12
• GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 12
• 239000008194 pharmaceutical composition Substances 0.000 claims description 11
• 125000004432 carbon atom Chemical group C* 0.000 claims description 10
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
• 125000005841 biaryl group Chemical group 0.000 claims description 7
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
• 229910052727 yttrium Inorganic materials 0.000 claims description 6
• 125000004429 atom Chemical group 0.000 claims description 5
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 5
• 241000124008 Mammalia Species 0.000 claims description 4
• 150000001336 alkenes Chemical class 0.000 claims description 4
• 125000004181 carboxyalkyl group Chemical group 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
• PAMQUYCMYTUMJW-KRWDZBQOSA-N (3s)-3-[[1-[(2-chlorophenyl)methyl]-4-hydroxy-2-oxopyridin-3-yl]carbamoylamino]-3-[3-(trifluoromethyl)phenyl]propanoic acid Chemical compound N([C@@H](CC(=O)O)C=1C=C(C=CC=1)C(F)(F)F)C(=O)NC(C1=O)=C(O)C=CN1CC1=CC=CC=C1Cl PAMQUYCMYTUMJW-KRWDZBQOSA-N 0.000 claims description 3
• KDYOFXPLHVSIHS-UHFFFAOYSA-N 2-(4-methylphenyl)propanoic acid Chemical compound OC(=O)C(C)C1=CC=C(C)C=C1 KDYOFXPLHVSIHS-UHFFFAOYSA-N 0.000 claims description 3
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 3
• 125000002619 bicyclic group Chemical group 0.000 claims description 3
• 125000004122 cyclic group Chemical group 0.000 claims description 3
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
• 150000002081 enamines Chemical class 0.000 claims description 3
• 125000005843 halogen group Chemical group 0.000 claims description 3
• 125000005842 heteroatom Chemical group 0.000 claims description 3
• 125000004043 oxo group Chemical group O=* 0.000 claims description 3
• 125000004434 sulfur atom Chemical group 0.000 claims description 3
• WMKLRNMTKRPGEL-FQEVSTJZSA-N (3s)-3-[[1-[(2-chloro-6-fluorophenyl)methyl]-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=CC=CN1CC1=C(F)C=CC=C1Cl WMKLRNMTKRPGEL-FQEVSTJZSA-N 0.000 claims description 2
• JPEASVDUPDPZHB-IBGZPJMESA-N (3s)-3-[[1-[(2-chlorophenyl)methyl]-4-hydroxy-2-oxopyridin-3-yl]carbamoylamino]-3-(3,5-dimethylphenyl)propanoic acid Chemical compound CC1=CC(C)=CC([C@H](CC(O)=O)NC(=O)NC=2C(N(CC=3C(=CC=CC=3)Cl)C=CC=2O)=O)=C1 JPEASVDUPDPZHB-IBGZPJMESA-N 0.000 claims description 2
• SVJORHDCZSSIIV-KRWDZBQOSA-N (3s)-3-[[1-[(2-chlorophenyl)methyl]-4-hydroxy-2-oxopyridin-3-yl]carbamoylamino]-3-phenylpropanoic acid Chemical compound N([C@@H](CC(=O)O)C=1C=CC=CC=1)C(=O)NC(C1=O)=C(O)C=CN1CC1=CC=CC=C1Cl SVJORHDCZSSIIV-KRWDZBQOSA-N 0.000 claims description 2
• XEHDSQSMOHDBQB-FQEVSTJZSA-N (3s)-3-[[1-[(2-chlorophenyl)methyl]-5-methyl-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=CC(C)=CN1CC1=CC=CC=C1Cl XEHDSQSMOHDBQB-FQEVSTJZSA-N 0.000 claims description 2
• JIYRLYKPKAOWDE-QFIPXVFZSA-N (3s)-3-[[1-benzyl-2-methyl-4-(2-methylpropyl)-6-oxopyrimidin-5-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound O=C1C(NC(=O)N[C@@H](CC(O)=O)C=2C=CC(C)=CC=2)=C(CC(C)C)N=C(C)N1CC1=CC=CC=C1 JIYRLYKPKAOWDE-QFIPXVFZSA-N 0.000 claims description 2
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
• 150000007513 acids Chemical class 0.000 claims description 2
• 125000006308 propyl amino group Chemical group 0.000 claims description 2
• 229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
• CEAOPVIFGJTFDW-SFHVURJKSA-N (3s)-3-[[1-[(2-chloro-6-fluorophenyl)methyl]-4-hydroxy-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=C(O)C=CN1CC1=C(F)C=CC=C1Cl CEAOPVIFGJTFDW-SFHVURJKSA-N 0.000 claims 1
• KNTDPRHBTCOYNN-IBGZPJMESA-N (3s)-3-[[1-[(2-chlorophenyl)methyl]-4-hydroxy-6-methyl-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=C(O)C=C(C)N1CC1=CC=CC=C1Cl KNTDPRHBTCOYNN-IBGZPJMESA-N 0.000 claims 1
• HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims 1
• 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims 1
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 1
• 125000001691 aryl alkyl amino group Chemical group 0.000 claims 1
• WPRTWBVDLDSWPU-UHFFFAOYSA-N cyano(nitro)carbamoperoxoic acid Chemical class OOC(=O)N(C#N)[N+]([O-])=O WPRTWBVDLDSWPU-UHFFFAOYSA-N 0.000 claims 1
• 238000004519 manufacturing process Methods 0.000 claims 1
• 125000004430 oxygen atom Chemical group O* 0.000 claims 1
• 108010000134 Vascular Cell Adhesion Molecule-1 Proteins 0.000 abstract description 19
• 102100023543 Vascular cell adhesion protein 1 Human genes 0.000 abstract description 19
• 108010067306 Fibronectins Proteins 0.000 abstract description 6
• 102000016359 Fibronectins Human genes 0.000 abstract description 6
• 206010020751 Hypersensitivity Diseases 0.000 abstract description 4
• 208000026935 allergic disease Diseases 0.000 abstract description 4
• 230000005764 inhibitory process Effects 0.000 abstract description 4
• 201000001320 Atherosclerosis Diseases 0.000 abstract description 3
• 230000007815 allergy Effects 0.000 abstract description 3
• 208000006673 asthma Diseases 0.000 abstract description 3
• 208000032839 leukemia Diseases 0.000 abstract description 3
• 201000006417 multiple sclerosis Diseases 0.000 abstract description 3
• 208000003174 Brain Neoplasms Diseases 0.000 abstract description 2
• XJBLYQPDBGBSNJ-QFIPXVFZSA-N (3s)-3-[[1-[(2-chlorophenyl)methyl]-2-oxo-4-propylpyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound O=C1C(NC(=O)N[C@@H](CC(O)=O)C=2C=CC(C)=CC=2)=C(CCC)C=CN1CC1=CC=CC=C1Cl XJBLYQPDBGBSNJ-QFIPXVFZSA-N 0.000 abstract 1
• 201000003068 rheumatic fever Diseases 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 356
• 239000000203 mixture Substances 0.000 description 184
• 239000000243 solution Substances 0.000 description 179
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 152
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 144
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 128
• 235000019439 ethyl acetate Nutrition 0.000 description 119
• 230000002829 reductive effect Effects 0.000 description 118
• 239000000706 filtrate Substances 0.000 description 111
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 93
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 90
• 238000000034 method Methods 0.000 description 75
• 239000012044 organic layer Substances 0.000 description 70
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 69
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 68
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 68
• 239000012267 brine Substances 0.000 description 68
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 65
• 239000007787 solid Substances 0.000 description 58
• 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 description 51
• 239000010410 layer Substances 0.000 description 48
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 43
• 230000015572 biosynthetic process Effects 0.000 description 43
• 238000003786 synthesis reaction Methods 0.000 description 42
• UUDALWDRIFYZPM-UHFFFAOYSA-N 1h-pyridine-2,4-dione Chemical compound O=C1CC(=O)C=CN1 UUDALWDRIFYZPM-UHFFFAOYSA-N 0.000 description 41
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 38
• 239000012299 nitrogen atmosphere Substances 0.000 description 38
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 37
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 36
• 210000004027 cell Anatomy 0.000 description 29
• 239000011541 reaction mixture Substances 0.000 description 29
• 238000000746 purification Methods 0.000 description 26
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 24
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
• 238000010898 silica gel chromatography Methods 0.000 description 24
• 239000000725 suspension Substances 0.000 description 24
• 239000012141 concentrate Substances 0.000 description 23
• 235000008504 concentrate Nutrition 0.000 description 23
• SORGEQQSQGNZFI-UHFFFAOYSA-N [azido(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(N=[N+]=[N-])OC1=CC=CC=C1 SORGEQQSQGNZFI-UHFFFAOYSA-N 0.000 description 21
• 239000000463 material Substances 0.000 description 21
• 238000010992 reflux Methods 0.000 description 21
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 20
• 125000006319 alkynyl amino group Chemical group 0.000 description 19
• 150000003254 radicals Chemical class 0.000 description 19
• 239000000741 silica gel Substances 0.000 description 19
• 229910002027 silica gel Inorganic materials 0.000 description 19
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
• 125000002877 alkyl aryl group Chemical group 0.000 description 18
• YZYSBLIHZXONPY-UHFFFAOYSA-N [1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound O1C(N=C2C(N=CC=C21)=O)=O YZYSBLIHZXONPY-UHFFFAOYSA-N 0.000 description 17
• 239000008346 aqueous phase Substances 0.000 description 17
• 239000012298 atmosphere Substances 0.000 description 17
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 16
• 210000000265 leukocyte Anatomy 0.000 description 16
• 239000003921 oil Substances 0.000 description 16
• 235000019198 oils Nutrition 0.000 description 16
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
• 238000006243 chemical reaction Methods 0.000 description 15
• 150000002431 hydrogen Chemical class 0.000 description 15
• 229910000104 sodium hydride Inorganic materials 0.000 description 15
• 125000004183 alkoxy alkyl group Chemical group 0.000 description 14
• 239000012074 organic phase Substances 0.000 description 14
• 239000011734 sodium Substances 0.000 description 14
• 229960000583 acetic acid Drugs 0.000 description 12
• 150000001412 amines Chemical class 0.000 description 12
• 150000005347 biaryls Chemical group 0.000 description 12
• 239000006185 dispersion Substances 0.000 description 12
• 235000019441 ethanol Nutrition 0.000 description 12
• MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 12
• 229910052717 sulfur Inorganic materials 0.000 description 12
• ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 11
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 11
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 11
• 239000002480 mineral oil Substances 0.000 description 11
• 235000010446 mineral oil Nutrition 0.000 description 11
• KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 10
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 10
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 10
• 201000010099 disease Diseases 0.000 description 10
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 10
• 229940079593 drug Drugs 0.000 description 10
• 239000006260 foam Substances 0.000 description 10
• 238000003756 stirring Methods 0.000 description 10
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
• 239000012362 glacial acetic acid Substances 0.000 description 9
• 210000001519 tissue Anatomy 0.000 description 9
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
• 239000000284 extract Substances 0.000 description 8
• 238000009472 formulation Methods 0.000 description 8
• 239000000843 powder Substances 0.000 description 8
• 238000002360 preparation method Methods 0.000 description 8
• 102000004169 proteins and genes Human genes 0.000 description 8
• 108090000623 proteins and genes Proteins 0.000 description 8
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 7
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 7
• 125000002252 acyl group Chemical group 0.000 description 7
• 125000001931 aliphatic group Chemical group 0.000 description 7
• 239000005457 ice water Substances 0.000 description 7
• 239000002502 liposome Substances 0.000 description 7
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
• QNAYBMKLOCPYGJ-UHFFFAOYSA-N Alanine Chemical compound CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 6
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
• LWLVRCAFNCMORL-UHFFFAOYSA-N O1C(NC2C1=CC=NC2=O)=O Chemical compound O1C(NC2C1=CC=NC2=O)=O LWLVRCAFNCMORL-UHFFFAOYSA-N 0.000 description 6
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
• YKOWBJJOJNGCAD-SHYZEUOFSA-N [(2r,3s,5r)-3-hydroxy-5-[4-(hydroxyamino)-2-oxopyrimidin-1-yl]oxolan-2-yl]methyl dihydrogen phosphate Chemical compound O=C1N=C(NO)C=CN1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)C1 YKOWBJJOJNGCAD-SHYZEUOFSA-N 0.000 description 6
• 125000003277 amino group Chemical group 0.000 description 6
• 150000004657 carbamic acid derivatives Chemical class 0.000 description 6
• 235000013877 carbamide Nutrition 0.000 description 6
• 229940126214 compound 3 Drugs 0.000 description 6
• 150000002148 esters Chemical class 0.000 description 6
• 238000001914 filtration Methods 0.000 description 6
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 6
• 239000000546 pharmaceutical excipient Substances 0.000 description 6
• 239000000651 prodrug Substances 0.000 description 6
• 229940002612 prodrug Drugs 0.000 description 6
• 239000001294 propane Substances 0.000 description 6
• 239000000126 substance Substances 0.000 description 6
• 239000003656 tris buffered saline Substances 0.000 description 6
• 239000011701 zinc Substances 0.000 description 6
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 5
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 5
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 5
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 5
• JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 5
• 238000010521 absorption reaction Methods 0.000 description 5
• 239000004202 carbamide Substances 0.000 description 5
• 239000000969 carrier Substances 0.000 description 5
• 239000003085 diluting agent Substances 0.000 description 5
• 230000000694 effects Effects 0.000 description 5
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 5
• YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 5
• 210000004698 lymphocyte Anatomy 0.000 description 5
• 210000001616 monocyte Anatomy 0.000 description 5
• 229910052763 palladium Inorganic materials 0.000 description 5
• 229920001223 polyethylene glycol Polymers 0.000 description 5
• 239000002244 precipitate Substances 0.000 description 5
• 239000000047 product Substances 0.000 description 5
• 238000010791 quenching Methods 0.000 description 5
• KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 4
• MQHULLOCAJMXJU-UHFFFAOYSA-N 2-(2-methylphenyl)propanoic acid Chemical compound OC(=O)C(C)C1=CC=CC=C1C MQHULLOCAJMXJU-UHFFFAOYSA-N 0.000 description 4
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
• DQLHSFUMICQIMB-UHFFFAOYSA-N 2-azaniumyl-3-(4-methylphenyl)propanoate Chemical compound CC1=CC=C(CC(N)C(O)=O)C=C1 DQLHSFUMICQIMB-UHFFFAOYSA-N 0.000 description 4
• OGVSVJLQFRZSPX-UHFFFAOYSA-N 3,5-dihydro-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound O=c1[nH]c2c(cc[nH]c2=O)o1 OGVSVJLQFRZSPX-UHFFFAOYSA-N 0.000 description 4
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 4
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 4
• 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 4
• BGGALFIXXQOTPY-NRFANRHFSA-N C1(=C(C2=C(C=C1)N(C(C#N)=C2)C[C@@H](N1CCN(CC1)S(=O)(=O)C)C)C)CN1CCC(CC1)NC1=NC(=NC2=C1C=C(S2)CC(F)(F)F)NC Chemical compound C1(=C(C2=C(C=C1)N(C(C#N)=C2)C[C@@H](N1CCN(CC1)S(=O)(=O)C)C)C)CN1CCC(CC1)NC1=NC(=NC2=C1C=C(S2)CC(F)(F)F)NC BGGALFIXXQOTPY-NRFANRHFSA-N 0.000 description 4
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
• YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 4
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
• 125000004414 alkyl thio group Chemical group 0.000 description 4
• 150000001408 amides Chemical class 0.000 description 4
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
• 230000021164 cell adhesion Effects 0.000 description 4
• 239000003795 chemical substances by application Substances 0.000 description 4
• 238000004587 chromatography analysis Methods 0.000 description 4
• 239000012230 colorless oil Substances 0.000 description 4
• 229940125877 compound 31 Drugs 0.000 description 4
• 229920001971 elastomer Polymers 0.000 description 4
• 239000002024 ethyl acetate extract Substances 0.000 description 4
• 238000003818 flash chromatography Methods 0.000 description 4
• 210000003714 granulocyte Anatomy 0.000 description 4
• 208000015181 infectious disease Diseases 0.000 description 4
• 239000003112 inhibitor Substances 0.000 description 4
• 239000007924 injection Substances 0.000 description 4
• 238000002347 injection Methods 0.000 description 4
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
• 125000005647 linker group Chemical group 0.000 description 4
• 238000001819 mass spectrum Methods 0.000 description 4
• 238000002844 melting Methods 0.000 description 4
• 230000008018 melting Effects 0.000 description 4
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 4
• 231100000252 nontoxic Toxicity 0.000 description 4
• 230000003000 nontoxic effect Effects 0.000 description 4
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
• 239000002151 riboflavin Substances 0.000 description 4
• 239000011780 sodium chloride Substances 0.000 description 4
• 239000012312 sodium hydride Substances 0.000 description 4
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
• 239000002904 solvent Substances 0.000 description 4
• 125000001544 thienyl group Chemical group 0.000 description 4
• ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 4
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
• QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
• UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 3
• LHXSMCYMHLUFOG-UHFFFAOYSA-N (2-chloro-6-ethoxyphenyl)methanamine Chemical compound CCOC1=CC=CC(Cl)=C1CN LHXSMCYMHLUFOG-UHFFFAOYSA-N 0.000 description 3
• STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 description 3
• WJUJLVWFAWUKRU-FQEVSTJZSA-N (3s)-3-[(3-benzyl-5-chloro-2-hydroxyphenyl)carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC1=CC(Cl)=CC(CC=2C=CC=CC=2)=C1O WJUJLVWFAWUKRU-FQEVSTJZSA-N 0.000 description 3
• BASMANVIUSSIIM-UHFFFAOYSA-N 1-chloro-2-(chloromethyl)benzene Chemical compound ClCC1=CC=CC=C1Cl BASMANVIUSSIIM-UHFFFAOYSA-N 0.000 description 3
• QQWACHGKILUHGB-UHFFFAOYSA-N 2-isocyanatopropanoic acid Chemical compound OC(=O)C(C)N=C=O QQWACHGKILUHGB-UHFFFAOYSA-N 0.000 description 3
• 125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 description 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
• 108091003079 Bovine Serum Albumin Proteins 0.000 description 3
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 3
• 229910004373 HOAc Inorganic materials 0.000 description 3
• 241001465754 Metazoa Species 0.000 description 3
• 206010028980 Neoplasm Diseases 0.000 description 3
• 239000002671 adjuvant Substances 0.000 description 3
• 235000010443 alginic acid Nutrition 0.000 description 3
• 229920000615 alginic acid Polymers 0.000 description 3
• 125000002947 alkylene group Chemical group 0.000 description 3
• 229940024606 amino acid Drugs 0.000 description 3
• 235000019270 ammonium chloride Nutrition 0.000 description 3
• 125000004391 aryl sulfonyl group Chemical group 0.000 description 3
• XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 description 3
• 239000002585 base Substances 0.000 description 3
• 210000003651 basophil Anatomy 0.000 description 3
• 230000008901 benefit Effects 0.000 description 3
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
• KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 description 3
• 239000012148 binding buffer Substances 0.000 description 3
• 229920002988 biodegradable polymer Polymers 0.000 description 3
• 239000004621 biodegradable polymer Substances 0.000 description 3
• 229940098773 bovine serum albumin Drugs 0.000 description 3
• 239000002775 capsule Substances 0.000 description 3
• 229910002091 carbon monoxide Inorganic materials 0.000 description 3
• 229940125833 compound 23 Drugs 0.000 description 3
• 229940125961 compound 24 Drugs 0.000 description 3
• 229940125878 compound 36 Drugs 0.000 description 3
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
• 230000006378 damage Effects 0.000 description 3
• 239000003599 detergent Substances 0.000 description 3
• FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 3
• 239000002552 dosage form Substances 0.000 description 3
• 239000003480 eluent Substances 0.000 description 3
• 238000010828 elution Methods 0.000 description 3
• 239000003995 emulsifying agent Substances 0.000 description 3
• 210000002889 endothelial cell Anatomy 0.000 description 3
• 210000003979 eosinophil Anatomy 0.000 description 3
• 150000002170 ethers Chemical class 0.000 description 3
• 239000007789 gas Substances 0.000 description 3
• 125000005343 heterocyclic alkyl group Chemical group 0.000 description 3
• 239000008241 heterogeneous mixture Substances 0.000 description 3
• 239000012456 homogeneous solution Substances 0.000 description 3
• 238000001727 in vivo Methods 0.000 description 3
• 238000002955 isolation Methods 0.000 description 3
• 150000002632 lipids Chemical class 0.000 description 3
• 239000007788 liquid Substances 0.000 description 3
• 230000001404 mediated effect Effects 0.000 description 3
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 3
• TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 3
• 230000005012 migration Effects 0.000 description 3
• 238000013508 migration Methods 0.000 description 3
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 3
• 230000003287 optical effect Effects 0.000 description 3
• 150000007524 organic acids Chemical class 0.000 description 3
• 239000006187 pill Substances 0.000 description 3
• NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
• 239000003755 preservative agent Substances 0.000 description 3
• 108090000765 processed proteins & peptides Proteins 0.000 description 3
• 229910052708 sodium Inorganic materials 0.000 description 3
• MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 3
• 239000003826 tablet Substances 0.000 description 3
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
• 238000005406 washing Methods 0.000 description 3
• PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
• ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 description 2
• AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 2
• ZYZHMSJNPCYUTB-CYBMUJFWSA-N (1r)-n-benzyl-1-phenylethanamine Chemical compound N([C@H](C)C=1C=CC=CC=1)CC1=CC=CC=C1 ZYZHMSJNPCYUTB-CYBMUJFWSA-N 0.000 description 2
• SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 2
• KDDNKZCVYQDGKE-UHFFFAOYSA-N (2-chlorophenyl)methanamine Chemical compound NCC1=CC=CC=C1Cl KDDNKZCVYQDGKE-UHFFFAOYSA-N 0.000 description 2
• GCTFTMWXZFLTRR-GFCCVEGCSA-N (2r)-2-amino-n-[3-(difluoromethoxy)-4-(1,3-oxazol-5-yl)phenyl]-4-methylpentanamide Chemical compound FC(F)OC1=CC(NC(=O)[C@H](N)CC(C)C)=CC=C1C1=CN=CO1 GCTFTMWXZFLTRR-GFCCVEGCSA-N 0.000 description 2
• QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 2
• IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 2
• UDQTXCHQKHIQMH-KYGLGHNPSA-N (3ar,5s,6s,7r,7ar)-5-(difluoromethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](C(F)F)[C@@H](O)[C@@H]2O UDQTXCHQKHIQMH-KYGLGHNPSA-N 0.000 description 2
• HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 description 2
• PDKBZSHASZPMSX-HSTJUUNISA-N (3s)-3-(4-chloro-4-methylcyclohexa-1,5-dien-1-yl)-3-[[1-[(2-chlorophenyl)methyl]-2-oxopyridin-3-yl]carbamoylamino]propanoic acid Chemical compound C1=CC(C)(Cl)CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=CC=CN1CC1=CC=CC=C1Cl PDKBZSHASZPMSX-HSTJUUNISA-N 0.000 description 2
• BSOCOIAYGTZIOJ-IBGZPJMESA-N (3s)-3-[(1-benzyl-2-methyl-6-oxopyrimidin-5-yl)carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=CN=C(C)N1CC1=CC=CC=C1 BSOCOIAYGTZIOJ-IBGZPJMESA-N 0.000 description 2
• YFSGACWYJRMDHV-NRFANRHFSA-N (3s)-3-[[1-[(2-chlorophenyl)methyl]-4-ethyl-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound O=C1C(NC(=O)N[C@@H](CC(O)=O)C=2C=CC(C)=CC=2)=C(CC)C=CN1CC1=CC=CC=C1Cl YFSGACWYJRMDHV-NRFANRHFSA-N 0.000 description 2
• PAFJVIUWHNDLIN-IBGZPJMESA-N (3s)-3-[[1-[(2-chlorophenyl)methyl]-4-fluoro-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=C(F)C=CN1CC1=CC=CC=C1Cl PAFJVIUWHNDLIN-IBGZPJMESA-N 0.000 description 2
• YQOLEILXOBUDMU-KRWDZBQOSA-N (4R)-5-[(6-bromo-3-methyl-2-pyrrolidin-1-ylquinoline-4-carbonyl)amino]-4-(2-chlorophenyl)pentanoic acid Chemical compound CC1=C(C2=C(C=CC(=C2)Br)N=C1N3CCCC3)C(=O)NC[C@H](CCC(=O)O)C4=CC=CC=C4Cl YQOLEILXOBUDMU-KRWDZBQOSA-N 0.000 description 2
• WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 2
• ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 2
• PHQKPTUMYZCVMM-UHFFFAOYSA-N 1-chloro-2-(chloromethyl)-3-ethoxybenzene Chemical compound CCOC1=CC=CC(Cl)=C1CCl PHQKPTUMYZCVMM-UHFFFAOYSA-N 0.000 description 2
• VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
• PAYROHWFGZADBR-UHFFFAOYSA-N 2-[[4-amino-5-(5-iodo-4-methoxy-2-propan-2-ylphenoxy)pyrimidin-2-yl]amino]propane-1,3-diol Chemical compound C1=C(I)C(OC)=CC(C(C)C)=C1OC1=CN=C(NC(CO)CO)N=C1N PAYROHWFGZADBR-UHFFFAOYSA-N 0.000 description 2
• YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 2
• TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 2
• MXJYARUABCVQLQ-UHFFFAOYSA-N 2-chloro-6-ethoxybenzonitrile Chemical compound CCOC1=CC=CC(Cl)=C1C#N MXJYARUABCVQLQ-UHFFFAOYSA-N 0.000 description 2
• LFOIDLOIBZFWDO-UHFFFAOYSA-N 2-methoxy-6-[6-methoxy-4-[(3-phenylmethoxyphenyl)methoxy]-1-benzofuran-2-yl]imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=C2SC(OC)=NN2C=C1C(OC1=CC(OC)=C2)=CC1=C2OCC(C=1)=CC=CC=1OCC1=CC=CC=C1 LFOIDLOIBZFWDO-UHFFFAOYSA-N 0.000 description 2
• QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 2
• BGXRYRSCOCRYBQ-UHFFFAOYSA-N 3-chloro-2-[(2,4-dioxo-3h-[1,3]oxazolo[4,5-c]pyridin-5-yl)methyl]benzonitrile Chemical compound ClC1=CC=CC(C#N)=C1CN1C(=O)C(NC(=O)O2)=C2C=C1 BGXRYRSCOCRYBQ-UHFFFAOYSA-N 0.000 description 2
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 2
• 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 description 2
• YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 description 2
• BOAFCICMVMFLIT-UHFFFAOYSA-N 3-nitro-1h-pyridin-2-one Chemical compound OC1=NC=CC=C1[N+]([O-])=O BOAFCICMVMFLIT-UHFFFAOYSA-N 0.000 description 2
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
• WYFCZWSWFGJODV-MIANJLSGSA-N 4-[[(1s)-2-[(e)-3-[3-chloro-2-fluoro-6-(tetrazol-1-yl)phenyl]prop-2-enoyl]-5-(4-methyl-2-oxopiperazin-1-yl)-3,4-dihydro-1h-isoquinoline-1-carbonyl]amino]benzoic acid Chemical compound O=C1CN(C)CCN1C1=CC=CC2=C1CCN(C(=O)\C=C\C=1C(=CC=C(Cl)C=1F)N1N=NN=C1)[C@@H]2C(=O)NC1=CC=C(C(O)=O)C=C1 WYFCZWSWFGJODV-MIANJLSGSA-N 0.000 description 2
• MPMKMQHJHDHPBE-RUZDIDTESA-N 4-[[(2r)-1-(1-benzothiophene-3-carbonyl)-2-methylazetidine-2-carbonyl]-[(3-chlorophenyl)methyl]amino]butanoic acid Chemical compound O=C([C@@]1(N(CC1)C(=O)C=1C2=CC=CC=C2SC=1)C)N(CCCC(O)=O)CC1=CC=CC(Cl)=C1 MPMKMQHJHDHPBE-RUZDIDTESA-N 0.000 description 2
• BIUDHHGROGJSHN-UHFFFAOYSA-N 4-fluoro-3-(trifluoromethyl)benzaldehyde Chemical group FC1=CC=C(C=O)C=C1C(F)(F)F BIUDHHGROGJSHN-UHFFFAOYSA-N 0.000 description 2
• 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 2
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
• DSTZRAZSNWAZIY-UHFFFAOYSA-N 5-(pyridin-2-ylmethyl)-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound O1C(=O)NC(C2=O)=C1C=CN2CC1=CC=CC=N1 DSTZRAZSNWAZIY-UHFFFAOYSA-N 0.000 description 2
• SIPURNCUNDMZHI-UHFFFAOYSA-N 5-[(2,3-dichlorophenyl)methyl]-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound ClC1=CC=CC(CN2C(C=3NC(=O)OC=3C=C2)=O)=C1Cl SIPURNCUNDMZHI-UHFFFAOYSA-N 0.000 description 2
• REEHGJBMJSCWRI-UHFFFAOYSA-N 5-[(2,4-dichlorophenyl)methyl]-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound ClC1=CC(Cl)=CC=C1CN1C(=O)C(NC(=O)O2)=C2C=C1 REEHGJBMJSCWRI-UHFFFAOYSA-N 0.000 description 2
• CLNHGKWUXLAOOJ-UHFFFAOYSA-N 5-[(2,4-difluorophenyl)methyl]-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound FC1=CC(F)=CC=C1CN1C(=O)C(NC(=O)O2)=C2C=C1 CLNHGKWUXLAOOJ-UHFFFAOYSA-N 0.000 description 2
• XMHISXICUBQNMC-UHFFFAOYSA-N 5-[(2,5-difluorophenyl)methyl]-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound FC1=CC=C(F)C(CN2C(C=3NC(=O)OC=3C=C2)=O)=C1 XMHISXICUBQNMC-UHFFFAOYSA-N 0.000 description 2
• JHQDBUNUHQTXIF-UHFFFAOYSA-N 5-[(2,5-dimethylphenyl)methyl]-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound CC1=CC=C(C)C(CN2C(C=3NC(=O)OC=3C=C2)=O)=C1 JHQDBUNUHQTXIF-UHFFFAOYSA-N 0.000 description 2
• ZXQAFRNZBLKLCH-UHFFFAOYSA-N 5-[(2,6-dichlorophenyl)methyl]-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound ClC1=CC=CC(Cl)=C1CN1C(=O)C(NC(=O)O2)=C2C=C1 ZXQAFRNZBLKLCH-UHFFFAOYSA-N 0.000 description 2
• KXBGNTYUPQDBII-UHFFFAOYSA-N 5-[(2,6-dimethoxyphenyl)methyl]-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound COC1=CC=CC(OC)=C1CN1C(=O)C(NC(=O)O2)=C2C=C1 KXBGNTYUPQDBII-UHFFFAOYSA-N 0.000 description 2
• FDTHJDKPBQRHIM-UHFFFAOYSA-N 5-[(2,6-dimethylphenyl)methyl]-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound CC1=CC=CC(C)=C1CN1C(=O)C(NC(=O)O2)=C2C=C1 FDTHJDKPBQRHIM-UHFFFAOYSA-N 0.000 description 2
• SQOZHBVFGLKGRE-UHFFFAOYSA-N 5-[(2-bromophenyl)methyl]-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound BrC1=CC=CC=C1CN1C(=O)C(NC(=O)O2)=C2C=C1 SQOZHBVFGLKGRE-UHFFFAOYSA-N 0.000 description 2
• KGYOUOMGPFGKBP-UHFFFAOYSA-N 5-[(2-chloro-5-methylsulfonylphenyl)methyl]-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound CS(=O)(=O)C1=CC=C(Cl)C(CN2C(C=3NC(=O)OC=3C=C2)=O)=C1 KGYOUOMGPFGKBP-UHFFFAOYSA-N 0.000 description 2
• DCAZNMXRDRNRIF-UHFFFAOYSA-N 5-[(2-chloro-5-piperidin-1-ylsulfonylphenyl)methyl]-7-methyl-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound O=C1C=2NC(=O)OC=2C(C)=CN1CC(C(=CC=1)Cl)=CC=1S(=O)(=O)N1CCCCC1 DCAZNMXRDRNRIF-UHFFFAOYSA-N 0.000 description 2
• XDNLAKVASVIEMD-UHFFFAOYSA-N 5-[(2-chloro-6-ethoxyphenyl)methyl]-7-ethyl-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound CCOC1=CC=CC(Cl)=C1CN1C(=O)C(NC(=O)O2)=C2C(CC)=C1 XDNLAKVASVIEMD-UHFFFAOYSA-N 0.000 description 2
• ILHIAUNXUAGCCE-UHFFFAOYSA-N 5-[(2-chloro-6-fluorophenyl)methyl]-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound FC1=CC=CC(Cl)=C1CN1C(=O)C(NC(=O)O2)=C2C=C1 ILHIAUNXUAGCCE-UHFFFAOYSA-N 0.000 description 2
• JWHHZPCJWPFOAV-UHFFFAOYSA-N 5-[(2-chloro-6-methoxyphenyl)methyl]-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound COC1=CC=CC(Cl)=C1CN1C(=O)C(NC(=O)O2)=C2C=C1 JWHHZPCJWPFOAV-UHFFFAOYSA-N 0.000 description 2
• CWAODYWPKIAKAF-UHFFFAOYSA-N 5-[(2-chloro-6-methoxyphenyl)methyl]-7-methyl-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound COC1=CC=CC(Cl)=C1CN1C(=O)C(NC(=O)O2)=C2C(C)=C1 CWAODYWPKIAKAF-UHFFFAOYSA-N 0.000 description 2
• KQVQFFQYGSUMKU-UHFFFAOYSA-N 5-[(2-chloro-6-methoxyphenyl)methyl]-7-propyl-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound O=C1C=2NC(=O)OC=2C(CCC)=CN1CC1=C(Cl)C=CC=C1OC KQVQFFQYGSUMKU-UHFFFAOYSA-N 0.000 description 2
• NUYJOWOGUVGFTH-UHFFFAOYSA-N 5-[(2-chloro-6-propoxyphenyl)methyl]-7-methyl-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound CCCOC1=CC=CC(Cl)=C1CN1C(=O)C(NC(=O)O2)=C2C(C)=C1 NUYJOWOGUVGFTH-UHFFFAOYSA-N 0.000 description 2
• MCEPLFMGFMHIGR-UHFFFAOYSA-N 5-[(2-chlorophenyl)methyl]-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound ClC1=CC=CC=C1CN1C(=O)C(NC(=O)O2)=C2C=C1 MCEPLFMGFMHIGR-UHFFFAOYSA-N 0.000 description 2
• UEGXAKXHNJBPMF-UHFFFAOYSA-N 5-[(2-chlorophenyl)methyl]-6-methyl-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound CC1=CC=2OC(=O)NC=2C(=O)N1CC1=CC=CC=C1Cl UEGXAKXHNJBPMF-UHFFFAOYSA-N 0.000 description 2
• KCKFHXGOLIIEDD-UHFFFAOYSA-N 5-[(2-chlorophenyl)methyl]-7-pentyl-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound O=C1C=2NC(=O)OC=2C(CCCCC)=CN1CC1=CC=CC=C1Cl KCKFHXGOLIIEDD-UHFFFAOYSA-N 0.000 description 2
• GJEYQOMOKBLUON-UHFFFAOYSA-N 5-[(2-chlorophenyl)methyl]-7-propyl-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound O=C1C=2NC(=O)OC=2C(CCC)=CN1CC1=CC=CC=C1Cl GJEYQOMOKBLUON-UHFFFAOYSA-N 0.000 description 2
• VMKGDBHLZOSUFB-UHFFFAOYSA-N 5-[(2-fluorophenyl)methyl]-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound FC1=CC=CC=C1CN1C(=O)C(NC(=O)O2)=C2C=C1 VMKGDBHLZOSUFB-UHFFFAOYSA-N 0.000 description 2
• OTWJLSPVBDHQET-UHFFFAOYSA-N 5-[(2-methylsulfonylphenyl)methyl]-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound CS(=O)(=O)C1=CC=CC=C1CN1C(=O)C(NC(=O)O2)=C2C=C1 OTWJLSPVBDHQET-UHFFFAOYSA-N 0.000 description 2
• PBZXXCWWTUPWTE-UHFFFAOYSA-N 5-[(3,5-dimethylphenyl)methyl]-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound CC1=CC(C)=CC(CN2C(C=3NC(=O)OC=3C=C2)=O)=C1 PBZXXCWWTUPWTE-UHFFFAOYSA-N 0.000 description 2
• DXSARHWPYZOMRV-UHFFFAOYSA-N 5-[(3-chlorophenyl)methyl]-7-methyl-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound O=C1C=2NC(=O)OC=2C(C)=CN1CC1=CC=CC(Cl)=C1 DXSARHWPYZOMRV-UHFFFAOYSA-N 0.000 description 2
• YUIDSUOMBIBYOG-UHFFFAOYSA-N 5-[(3-methylphenyl)methyl]-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound CC1=CC=CC(CN2C(C=3NC(=O)OC=3C=C2)=O)=C1 YUIDSUOMBIBYOG-UHFFFAOYSA-N 0.000 description 2
• ZLFBRHGPMDFYHX-UHFFFAOYSA-N 5-[(4-chloro-2-methoxyphenyl)methyl]-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound COC1=CC(Cl)=CC=C1CN1C(=O)C(NC(=O)O2)=C2C=C1 ZLFBRHGPMDFYHX-UHFFFAOYSA-N 0.000 description 2
• BIIJKUZXXWVKGA-UHFFFAOYSA-N 5-[(4-methylphenyl)methyl]-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound C1=CC(C)=CC=C1CN1C(=O)C(NC(=O)O2)=C2C=C1 BIIJKUZXXWVKGA-UHFFFAOYSA-N 0.000 description 2
• SJWCLIPUIRSJFR-UHFFFAOYSA-N 5-[[2-(trifluoromethyl)phenyl]methyl]-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound FC(F)(F)C1=CC=CC=C1CN1C(=O)C(NC(=O)O2)=C2C=C1 SJWCLIPUIRSJFR-UHFFFAOYSA-N 0.000 description 2
• FCTXOZKZNMRGDL-UHFFFAOYSA-N 5-[[3,5-bis(trifluoromethyl)phenyl]methyl]-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(CN2C(C=3NC(=O)OC=3C=C2)=O)=C1 FCTXOZKZNMRGDL-UHFFFAOYSA-N 0.000 description 2
• GWYYSPSNZIUCMR-UHFFFAOYSA-N 5-[[3-(trifluoromethoxy)phenyl]methyl]-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound FC(F)(F)OC1=CC=CC(CN2C(C=3NC(=O)OC=3C=C2)=O)=C1 GWYYSPSNZIUCMR-UHFFFAOYSA-N 0.000 description 2
• XFJBGINZIMNZBW-CRAIPNDOSA-N 5-chloro-2-[4-[(1r,2s)-2-[2-(5-methylsulfonylpyridin-2-yl)oxyethyl]cyclopropyl]piperidin-1-yl]pyrimidine Chemical compound N1=CC(S(=O)(=O)C)=CC=C1OCC[C@H]1[C@@H](C2CCN(CC2)C=2N=CC(Cl)=CN=2)C1 XFJBGINZIMNZBW-CRAIPNDOSA-N 0.000 description 2
• IJRKLHTZAIFUTB-UHFFFAOYSA-N 5-nitro-2-(2-phenylethylamino)benzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC=C1NCCC1=CC=CC=C1 IJRKLHTZAIFUTB-UHFFFAOYSA-N 0.000 description 2
• HCCNBKFJYUWLEX-UHFFFAOYSA-N 7-(6-methoxypyridin-3-yl)-1-(2-propoxyethyl)-3-(pyrazin-2-ylmethylamino)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1NCC1=CN=CC=N1 HCCNBKFJYUWLEX-UHFFFAOYSA-N 0.000 description 2
• OUQDWMSQLUOELS-JTQLQIEISA-N 7-methyl-5-[(1s)-1-phenylethyl]-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound C1([C@H](C)N2C(C=3NC(=O)OC=3C(C)=C2)=O)=CC=CC=C1 OUQDWMSQLUOELS-JTQLQIEISA-N 0.000 description 2
• VQGZGWITRNDBAS-UHFFFAOYSA-N 7-methyl-5-[(4-methylphenyl)methyl]-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound C1=CC(C)=CC=C1CN1C(=O)C(NC(=O)O2)=C2C(C)=C1 VQGZGWITRNDBAS-UHFFFAOYSA-N 0.000 description 2
• IRBAWVGZNJIROV-SFHVURJKSA-N 9-(2-cyclopropylethynyl)-2-[[(2s)-1,4-dioxan-2-yl]methoxy]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(C#CC4CC4)C=C3CCN2C(=O)N=C1OC[C@@H]1COCCO1 IRBAWVGZNJIROV-SFHVURJKSA-N 0.000 description 2
• 229920001817 Agar Polymers 0.000 description 2
• GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
• 239000005995 Aluminium silicate Substances 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
• IYHHRZBKXXKDDY-UHFFFAOYSA-N BI-605906 Chemical compound N=1C=2SC(C(N)=O)=C(N)C=2C(C(F)(F)CC)=CC=1N1CCC(S(C)(=O)=O)CC1 IYHHRZBKXXKDDY-UHFFFAOYSA-N 0.000 description 2
• WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
• VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
• 229940126657 Compound 17 Drugs 0.000 description 2
• 229940127007 Compound 39 Drugs 0.000 description 2
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
• 108010010803 Gelatin Proteins 0.000 description 2
• 241000206672 Gelidium Species 0.000 description 2
• ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
• 241000282412 Homo Species 0.000 description 2
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
• 208000022559 Inflammatory bowel disease Diseases 0.000 description 2
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
• XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 2
• DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 2
• CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 2
• WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
• HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 2
• QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 2
• KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 2
• OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
• LIMFPAAAIVQRRD-BCGVJQADSA-N N-[2-[(3S,4R)-3-fluoro-4-methoxypiperidin-1-yl]pyrimidin-4-yl]-8-[(2R,3S)-2-methyl-3-(methylsulfonylmethyl)azetidin-1-yl]-5-propan-2-ylisoquinolin-3-amine Chemical compound F[C@H]1CN(CC[C@H]1OC)C1=NC=CC(=N1)NC=1N=CC2=C(C=CC(=C2C=1)C(C)C)N1[C@@H]([C@H](C1)CS(=O)(=O)C)C LIMFPAAAIVQRRD-BCGVJQADSA-N 0.000 description 2
• POFVJRKJJBFPII-UHFFFAOYSA-N N-cyclopentyl-5-[2-[[5-[(4-ethylpiperazin-1-yl)methyl]pyridin-2-yl]amino]-5-fluoropyrimidin-4-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound C1(CCCC1)NC=1SC(=C(N=1)C)C1=NC(=NC=C1F)NC1=NC=C(C=C1)CN1CCN(CC1)CC POFVJRKJJBFPII-UHFFFAOYSA-N 0.000 description 2
• OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 2
• 108010058846 Ovalbumin Proteins 0.000 description 2
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
• 239000002202 Polyethylene glycol Substances 0.000 description 2
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-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
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
• 229920002472 Starch Polymers 0.000 description 2
• CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
• 229930006000 Sucrose Natural products 0.000 description 2
• 239000007983 Tris buffer Substances 0.000 description 2
• 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 2
• LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 description 2
• SPXSEZMVRJLHQG-XMMPIXPASA-N [(2R)-1-[[4-[(3-phenylmethoxyphenoxy)methyl]phenyl]methyl]pyrrolidin-2-yl]methanol Chemical compound C(C1=CC=CC=C1)OC=1C=C(OCC2=CC=C(CN3[C@H](CCC3)CO)C=C2)C=CC=1 SPXSEZMVRJLHQG-XMMPIXPASA-N 0.000 description 2
• LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 2
• PSLUFJFHTBIXMW-WYEYVKMPSA-N [(3r,4ar,5s,6s,6as,10s,10ar,10bs)-3-ethenyl-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-6-(2-pyridin-2-ylethylcarbamoyloxy)-5,6,6a,8,9,10-hexahydro-2h-benzo[f]chromen-5-yl] acetate Chemical compound O([C@@H]1[C@@H]([C@]2(O[C@](C)(CC(=O)[C@]2(O)[C@@]2(C)[C@@H](O)CCC(C)(C)[C@@H]21)C=C)C)OC(=O)C)C(=O)NCCC1=CC=CC=N1 PSLUFJFHTBIXMW-WYEYVKMPSA-N 0.000 description 2
• SMNRFWMNPDABKZ-WVALLCKVSA-N [[(2R,3S,4R,5S)-5-(2,6-dioxo-3H-pyridin-3-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4S,5R,6R)-4-fluoro-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)C2C=CC(=O)NC2=O)[C@H](O)[C@@H](F)[C@@H]1O SMNRFWMNPDABKZ-WVALLCKVSA-N 0.000 description 2
• 239000004480 active ingredient Substances 0.000 description 2
• 239000000853 adhesive Substances 0.000 description 2
• 230000001070 adhesive effect Effects 0.000 description 2
• 235000010419 agar Nutrition 0.000 description 2
• 150000001298 alcohols Chemical class 0.000 description 2
• 150000001299 aldehydes Chemical class 0.000 description 2
• QBYJBZPUGVGKQQ-SJJAEHHWSA-N aldrin Chemical compound C1[C@H]2C=C[C@@H]1[C@H]1[C@@](C3(Cl)Cl)(Cl)C(Cl)=C(Cl)[C@@]3(Cl)[C@H]12 QBYJBZPUGVGKQQ-SJJAEHHWSA-N 0.000 description 2
• 125000005236 alkanoylamino group Chemical group 0.000 description 2
• 235000012211 aluminium silicate Nutrition 0.000 description 2
• 150000001413 amino acids Chemical class 0.000 description 2
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
• 239000007864 aqueous solution Substances 0.000 description 2
• 125000005125 aryl alkyl amino carbonyl group Chemical group 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
• 125000005605 benzo group Chemical group 0.000 description 2
• SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
• UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
• 229910052794 bromium Inorganic materials 0.000 description 2
• 150000001649 bromium compounds Chemical class 0.000 description 2
• 239000000872 buffer Substances 0.000 description 2
• 201000011510 cancer Diseases 0.000 description 2
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
• 125000001589 carboacyl group Chemical group 0.000 description 2
• 230000003197 catalytic effect Effects 0.000 description 2
• OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
• 125000000068 chlorophenyl group Chemical group 0.000 description 2
• 239000011247 coating layer Substances 0.000 description 2
• 229940126543 compound 14 Drugs 0.000 description 2
• 229940126142 compound 16 Drugs 0.000 description 2
• 229940125782 compound 2 Drugs 0.000 description 2
• 229940126086 compound 21 Drugs 0.000 description 2
• 229940125846 compound 25 Drugs 0.000 description 2
• 229940125851 compound 27 Drugs 0.000 description 2
• 229940127204 compound 29 Drugs 0.000 description 2
• 229940127573 compound 38 Drugs 0.000 description 2
• 229940126540 compound 41 Drugs 0.000 description 2
• 229940125936 compound 42 Drugs 0.000 description 2
• 229940125844 compound 46 Drugs 0.000 description 2
• 229940127271 compound 49 Drugs 0.000 description 2
• 229940125898 compound 5 Drugs 0.000 description 2
• 229940126545 compound 53 Drugs 0.000 description 2
• 229940125900 compound 59 Drugs 0.000 description 2
• 208000010247 contact dermatitis Diseases 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
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 2
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
• 229960001760 dimethyl sulfoxide Drugs 0.000 description 2
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
• MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 2
• 238000010410 dusting Methods 0.000 description 2
• 239000000839 emulsion Substances 0.000 description 2
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
• FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 2
• 239000013604 expression vector Substances 0.000 description 2
• 239000000945 filler Substances 0.000 description 2
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
• CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 description 2
• 125000002541 furyl group Chemical group 0.000 description 2
• 229920000159 gelatin Polymers 0.000 description 2
• 239000008273 gelatin Substances 0.000 description 2
• 235000019322 gelatine Nutrition 0.000 description 2
• 235000011852 gelatine desserts Nutrition 0.000 description 2
• 239000008187 granular material Substances 0.000 description 2
• 229940093915 gynecological organic acid Drugs 0.000 description 2
• YPGCWEMNNLXISK-UHFFFAOYSA-N hydratropic acid Chemical compound OC(=O)C(C)C1=CC=CC=C1 YPGCWEMNNLXISK-UHFFFAOYSA-N 0.000 description 2
• 238000011065 in-situ storage Methods 0.000 description 2
• 239000003701 inert diluent Substances 0.000 description 2
• 230000028709 inflammatory response Effects 0.000 description 2
• 239000004615 ingredient Substances 0.000 description 2
• 239000000543 intermediate Substances 0.000 description 2
• 150000004694 iodide salts Chemical class 0.000 description 2
• HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
• 230000007794 irritation Effects 0.000 description 2
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
• 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 2
• 150000003951 lactams Chemical class 0.000 description 2
• 239000008101 lactose Substances 0.000 description 2
• 239000008297 liquid dosage form Substances 0.000 description 2
• UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 2
• WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 2
• RENRQMCACQEWFC-UGKGYDQZSA-N lnp023 Chemical compound C1([C@H]2N(CC=3C=4C=CNC=4C(C)=CC=3OC)CC[C@@H](C2)OCC)=CC=C(C(O)=O)C=C1 RENRQMCACQEWFC-UGKGYDQZSA-N 0.000 description 2
• 206010025135 lupus erythematosus Diseases 0.000 description 2
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
• 235000019341 magnesium sulphate Nutrition 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
• 239000002609 medium Substances 0.000 description 2
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
• 244000005700 microbiome Species 0.000 description 2
• 150000007522 mineralic acids Chemical class 0.000 description 2
• IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 2
• 125000006504 o-cyanobenzyl group Chemical group [H]C1=C([H])C(C#N)=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
• 239000004006 olive oil Substances 0.000 description 2
• PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 2
• 235000005985 organic acids Nutrition 0.000 description 2
• 229940092253 ovalbumin Drugs 0.000 description 2
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
• 239000001301 oxygen Substances 0.000 description 2
• 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 2
• HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
• RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 2
• SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 2
• 229920000642 polymer Polymers 0.000 description 2
• 102000040430 polynucleotide Human genes 0.000 description 2
• 108091033319 polynucleotide Proteins 0.000 description 2
• 239000002157 polynucleotide Substances 0.000 description 2
• 229910052700 potassium Inorganic materials 0.000 description 2
• 239000011591 potassium Substances 0.000 description 2
• 125000000714 pyrimidinyl group Chemical group 0.000 description 2
• 230000000171 quenching effect Effects 0.000 description 2
• 206010039073 rheumatoid arthritis Diseases 0.000 description 2
• KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 2
• 235000010288 sodium nitrite Nutrition 0.000 description 2
• 239000012321 sodium triacetoxyborohydride Substances 0.000 description 2
• 235000019698 starch Nutrition 0.000 description 2
• 239000008107 starch Substances 0.000 description 2
• 239000007858 starting material Substances 0.000 description 2
• 238000007920 subcutaneous administration Methods 0.000 description 2
• 239000005720 sucrose Substances 0.000 description 2
• 229940124530 sulfonamide Drugs 0.000 description 2
• 150000003456 sulfonamides Chemical class 0.000 description 2
• 239000000829 suppository Substances 0.000 description 2
• 239000000375 suspending agent Substances 0.000 description 2
• 125000006318 tert-butyl amino group Chemical group [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
• 230000001225 therapeutic effect Effects 0.000 description 2
• 238000011200 topical administration Methods 0.000 description 2
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
• 229910052721 tungsten Inorganic materials 0.000 description 2
• 239000001993 wax Substances 0.000 description 2
• NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
• ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 1
• BKWVXPCYDRURMK-UHFFFAOYSA-N (2,6-dimethoxyphenyl)boronic acid Chemical compound COC1=CC=CC(OC)=C1B(O)O BKWVXPCYDRURMK-UHFFFAOYSA-N 0.000 description 1
• MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 1
• GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
• UNNLJKPOCSMMDA-LJQANCHMSA-N (2r)-2-[[1-[(2-chlorophenyl)methyl]-2-oxopyridin-3-yl]carbamoylamino]-3-phenylpropanoic acid Chemical compound C([C@H](C(=O)O)NC(=O)NC=1C(N(CC=2C(=CC=CC=2)Cl)C=CC=1)=O)C1=CC=CC=C1 UNNLJKPOCSMMDA-LJQANCHMSA-N 0.000 description 1
• IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 description 1
• JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
• YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 description 1
• VIJSPAIQWVPKQZ-BLECARSGSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-4-methylpentanoyl]amino]-4,4-dimethylpentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(C)=O VIJSPAIQWVPKQZ-BLECARSGSA-N 0.000 description 1
• LOGFVTREOLYCPF-KXNHARMFSA-N (2s,3r)-2-[[(2r)-1-[(2s)-2,6-diaminohexanoyl]pyrrolidine-2-carbonyl]amino]-3-hydroxybutanoic acid Chemical compound C[C@@H](O)[C@@H](C(O)=O)NC(=O)[C@H]1CCCN1C(=O)[C@@H](N)CCCCN LOGFVTREOLYCPF-KXNHARMFSA-N 0.000 description 1
• FNHHVPPSBFQMEL-KQHDFZBMSA-N (3S)-5-N-[(1S,5R)-3-hydroxy-6-bicyclo[3.1.0]hexanyl]-7-N,3-dimethyl-3-phenyl-2H-1-benzofuran-5,7-dicarboxamide Chemical compound CNC(=O)c1cc(cc2c1OC[C@@]2(C)c1ccccc1)C(=O)NC1[C@H]2CC(O)C[C@@H]12 FNHHVPPSBFQMEL-KQHDFZBMSA-N 0.000 description 1
• OOKAZRDERJMRCJ-KOUAFAAESA-N (3r)-7-[(1s,2s,4ar,6s,8s)-2,6-dimethyl-8-[(2s)-2-methylbutanoyl]oxy-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-hydroxy-5-oxoheptanoic acid Chemical compound C1=C[C@H](C)[C@H](CCC(=O)C[C@@H](O)CC(O)=O)C2[C@@H](OC(=O)[C@@H](C)CC)C[C@@H](C)C[C@@H]21 OOKAZRDERJMRCJ-KOUAFAAESA-N 0.000 description 1
• ZYIFKUNDDWVMAN-IBGZPJMESA-N (3s)-3-(1,3-benzodioxol-5-yl)-3-[(3-phenoxyphenyl)carbamoylamino]propanoic acid Chemical compound N([C@@H](CC(=O)O)C=1C=C2OCOC2=CC=1)C(=O)NC(C=1)=CC=CC=1OC1=CC=CC=C1 ZYIFKUNDDWVMAN-IBGZPJMESA-N 0.000 description 1
• FWTWKQHSRDBIAX-DQEYMECFSA-N (3s)-3-(1,3-benzodioxol-5-yl)-3-[[(3s)-1-[[4-[(2-methylphenyl)carbamoylamino]phenyl]methyl]-2-oxopiperidin-3-yl]carbamoylamino]propanoic acid Chemical compound CC1=CC=CC=C1NC(=O)NC(C=C1)=CC=C1CN1C(=O)[C@@H](NC(=O)N[C@@H](CC(O)=O)C=2C=C3OCOC3=CC=2)CCC1 FWTWKQHSRDBIAX-DQEYMECFSA-N 0.000 description 1
• ZCQCLGCOKCJUCV-HOTGVXAUSA-N (3s)-3-(1,3-benzodioxol-5-yl)-3-[[(3s)-2-oxo-1-(thiophen-2-ylmethyl)piperidin-3-yl]carbamoylamino]propanoic acid Chemical compound C([C@@H](C1=O)NC(=O)N[C@@H](CC(=O)O)C=2C=C3OCOC3=CC=2)CCN1CC1=CC=CS1 ZCQCLGCOKCJUCV-HOTGVXAUSA-N 0.000 description 1
• XBOZKEDWLVWFRM-SFHVURJKSA-N (3s)-3-(1,3-benzodioxol-5-yl)-3-[[1-[(3,5-dichlorophenyl)methyl]-2-oxopyridin-3-yl]carbamoylamino]propanoic acid Chemical compound N([C@@H](CC(=O)O)C=1C=C2OCOC2=CC=1)C(=O)NC(C1=O)=CC=CN1CC1=CC(Cl)=CC(Cl)=C1 XBOZKEDWLVWFRM-SFHVURJKSA-N 0.000 description 1
• VYBKJDKOONVIHC-SFHVURJKSA-N (3s)-3-(1,3-benzodioxol-5-yl)-3-[[3-(thiophen-2-ylmethylamino)phenyl]carbamoylamino]propanoic acid Chemical compound N([C@@H](CC(=O)O)C=1C=C2OCOC2=CC=1)C(=O)NC(C=1)=CC=CC=1NCC1=CC=CS1 VYBKJDKOONVIHC-SFHVURJKSA-N 0.000 description 1
• DXUDWWFMBZOVHS-KRWDZBQOSA-N (3s)-3-(3-fluorophenyl)-3-[[2-oxo-1-(thiophen-2-ylmethyl)pyridin-3-yl]carbamoylamino]propanoic acid Chemical compound N([C@@H](CC(=O)O)C=1C=C(F)C=CC=1)C(=O)NC(C1=O)=CC=CN1CC1=CC=CS1 DXUDWWFMBZOVHS-KRWDZBQOSA-N 0.000 description 1
• KADOZYGQZVMSBJ-HSTJUUNISA-N (3s)-3-(4-bromo-4-methylcyclohexa-1,5-dien-1-yl)-3-[[1-[(2-chlorophenyl)methyl]-2-oxopyridin-3-yl]carbamoylamino]propanoic acid Chemical compound C1=CC(C)(Br)CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=CC=CN1CC1=CC=CC=C1Cl KADOZYGQZVMSBJ-HSTJUUNISA-N 0.000 description 1
• JATKBPTWKYDPAX-IBGZPJMESA-N (3s)-3-(4-methylphenyl)-3-[[1-[(2-nitrophenyl)methyl]-2-oxopyridin-3-yl]carbamoylamino]propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=CC=CN1CC1=CC=CC=C1[N+]([O-])=O JATKBPTWKYDPAX-IBGZPJMESA-N 0.000 description 1
• WUSHFQHOKYBOLE-FQEVSTJZSA-N (3s)-3-(4-methylphenyl)-3-[[1-[(4-nitrophenyl)methyl]-2-oxopyridin-3-yl]carbamoylamino]propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=CC=CN1CC1=CC=C([N+]([O-])=O)C=C1 WUSHFQHOKYBOLE-FQEVSTJZSA-N 0.000 description 1
• DPONTFOHSATDJO-FQEVSTJZSA-N (3s)-3-(4-tert-butylphenyl)-3-[[2-oxo-1-(thiophen-2-ylmethyl)pyridin-3-yl]carbamoylamino]propanoic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=CC=CN1CC1=CC=CS1 DPONTFOHSATDJO-FQEVSTJZSA-N 0.000 description 1
• ADJKRRDOJRRWCC-IBGZPJMESA-N (3s)-3-[(1-benzyl-4-hydroxy-6-methyl-2-oxopyridin-3-yl)carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=C(O)C=C(C)N1CC1=CC=CC=C1 ADJKRRDOJRRWCC-IBGZPJMESA-N 0.000 description 1
• YCLGFAMMAQHUCP-QFIPXVFZSA-N (3s)-3-[(3-benzylphenyl)carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC1=CC=CC(CC=2C=CC=CC=2)=C1 YCLGFAMMAQHUCP-QFIPXVFZSA-N 0.000 description 1
• GNMBRVDWQXNSSA-KRWDZBQOSA-N (3s)-3-[4-fluoro-3-(trifluoromethyl)phenyl]-3-[[2-oxo-1-(thiophen-2-ylmethyl)pyridin-3-yl]carbamoylamino]propanoic acid Chemical compound N([C@@H](CC(=O)O)C=1C=C(C(F)=CC=1)C(F)(F)F)C(=O)NC(C1=O)=CC=CN1CC1=CC=CS1 GNMBRVDWQXNSSA-KRWDZBQOSA-N 0.000 description 1
• QHGQBRRMWTXPKE-IBGZPJMESA-N (3s)-3-[[1-[(2,3-dichlorophenyl)methyl]-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=CC=CN1CC1=CC=CC(Cl)=C1Cl QHGQBRRMWTXPKE-IBGZPJMESA-N 0.000 description 1
• HQAONAJJWZSWCN-FQEVSTJZSA-N (3s)-3-[[1-[(2,5-difluorophenyl)methyl]-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=CC=CN1CC1=CC(F)=CC=C1F HQAONAJJWZSWCN-FQEVSTJZSA-N 0.000 description 1
• FXQOVFYJPAKAII-FQEVSTJZSA-N (3s)-3-[[1-[(2,6-dichlorophenyl)methyl]-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=CC=CN1CC1=C(Cl)C=CC=C1Cl FXQOVFYJPAKAII-FQEVSTJZSA-N 0.000 description 1
• YWGJSUVJYTUELA-FQEVSTJZSA-N (3s)-3-[[1-[(2-bromo-5-fluorophenyl)methyl]-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=CC=CN1CC1=CC(F)=CC=C1Br YWGJSUVJYTUELA-FQEVSTJZSA-N 0.000 description 1
• QVXLATRWCVJLPE-IBGZPJMESA-N (3s)-3-[[1-[(2-bromophenyl)methyl]-2-oxopyridin-3-yl]carbamoylamino]-3-(3,4,5-trimethoxyphenyl)propanoic acid Chemical compound COC1=C(OC)C(OC)=CC([C@H](CC(O)=O)NC(=O)NC=2C(N(CC=3C(=CC=CC=3)Br)C=CC=2)=O)=C1 QVXLATRWCVJLPE-IBGZPJMESA-N 0.000 description 1
• QQWKDWJISNTBNF-FQEVSTJZSA-N (3s)-3-[[1-[(2-bromophenyl)methyl]-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=CC=CN1CC1=CC=CC=C1Br QQWKDWJISNTBNF-FQEVSTJZSA-N 0.000 description 1
• SMCNTIIYRBOTDR-FQEVSTJZSA-N (3s)-3-[[1-[(2-chloro-4-fluorophenyl)methyl]-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=CC=CN1CC1=CC=C(F)C=C1Cl SMCNTIIYRBOTDR-FQEVSTJZSA-N 0.000 description 1
• MBXWPHPJKFGZJU-NRFANRHFSA-N (3s)-3-[[1-[(2-chloro-5-methoxyphenyl)methyl]-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound COC1=CC=C(Cl)C(CN2C(C(NC(=O)N[C@@H](CC(O)=O)C=3C=CC(C)=CC=3)=CC=C2)=O)=C1 MBXWPHPJKFGZJU-NRFANRHFSA-N 0.000 description 1
• MKIYRELWYFXDNI-IBGZPJMESA-N (3s)-3-[[1-[(2-chloro-5-methylsulfonylphenyl)methyl]-4-hydroxy-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=C(O)C=CN1CC1=CC(S(C)(=O)=O)=CC=C1Cl MKIYRELWYFXDNI-IBGZPJMESA-N 0.000 description 1
• KVAPJFYQGHCQQT-NRFANRHFSA-N (3s)-3-[[1-[(2-chloro-6-ethoxyphenyl)methyl]-4-hydroxy-5-methyl-2-oxopyridin-3-yl]carbamoylamino]-3-(3-ethoxyphenyl)propanoic acid Chemical compound CCOC1=CC=CC([C@H](CC(O)=O)NC(=O)NC=2C(N(CC=3C(=CC=CC=3Cl)OCC)C=C(C)C=2O)=O)=C1 KVAPJFYQGHCQQT-NRFANRHFSA-N 0.000 description 1
• LZCFIYDGUKNJDM-QFIPXVFZSA-N (3s)-3-[[1-[(2-chloro-6-ethoxyphenyl)methyl]-5-cyclopropyl-4-hydroxy-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound CCOC1=CC=CC(Cl)=C1CN1C(=O)C(NC(=O)N[C@@H](CC(O)=O)C=2C=CC(C)=CC=2)=C(O)C(C2CC2)=C1 LZCFIYDGUKNJDM-QFIPXVFZSA-N 0.000 description 1
• GZPUNKYKUVROKR-QFIPXVFZSA-N (3s)-3-[[1-[(2-chloro-6-methylphenyl)methyl]-4-hydroxy-5,6-dimethyl-2-oxopyridin-3-yl]carbamoylamino]-3-(3,4-diethoxyphenyl)propanoic acid Chemical compound C1=C(OCC)C(OCC)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=C(O)C(C)=C(C)N1CC1=C(C)C=CC=C1Cl GZPUNKYKUVROKR-QFIPXVFZSA-N 0.000 description 1
• YVDIUNCGEKXUGF-VWLOTQADSA-N (3s)-3-[[1-[(2-chlorophenyl)methyl]-2-oxo-4-(pyridin-2-ylmethylamino)pyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C(N(CC=1C(=CC=CC=1)Cl)C=C1)=O)=C1NCC1=CC=CC=N1 YVDIUNCGEKXUGF-VWLOTQADSA-N 0.000 description 1
• RMWMYBLKSZBJDF-FQEVSTJZSA-N (3s)-3-[[1-[(2-chlorophenyl)methyl]-2-oxopyridin-3-yl]carbamoylamino]-3-(2,3-dihydro-1-benzofuran-5-yl)propanoic acid Chemical compound N([C@@H](CC(=O)O)C=1C=C2CCOC2=CC=1)C(=O)NC(C1=O)=CC=CN1CC1=CC=CC=C1Cl RMWMYBLKSZBJDF-FQEVSTJZSA-N 0.000 description 1
• LLAPTULCQVUOEA-INIZCTEOSA-N (3s)-3-[[1-[(2-chlorophenyl)methyl]-2-oxopyridin-3-yl]carbamoylamino]-3-(2,6-dihydroxyphenyl)propanoic acid Chemical compound N([C@@H](CC(=O)O)C=1C(=CC=CC=1O)O)C(=O)NC(C1=O)=CC=CN1CC1=CC=CC=C1Cl LLAPTULCQVUOEA-INIZCTEOSA-N 0.000 description 1
• RGXHISGDDLSQDC-SFHVURJKSA-N (3s)-3-[[1-[(2-chlorophenyl)methyl]-2-oxopyridin-3-yl]carbamoylamino]-3-(2,6-dimethoxyphenyl)propanoic acid Chemical compound COC1=CC=CC(OC)=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=CC=CN1CC1=CC=CC=C1Cl RGXHISGDDLSQDC-SFHVURJKSA-N 0.000 description 1
• WOGHRJVYIIPQGN-FQEVSTJZSA-N (3s)-3-[[1-[(2-chlorophenyl)methyl]-2-oxopyridin-3-yl]carbamoylamino]-3-(2-methylphenyl)propanoic acid Chemical compound CC1=CC=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=CC=CN1CC1=CC=CC=C1Cl WOGHRJVYIIPQGN-FQEVSTJZSA-N 0.000 description 1
• DSNCZDYTKGBUMO-NRFANRHFSA-N (3s)-3-[[1-[(2-chlorophenyl)methyl]-2-oxopyridin-3-yl]carbamoylamino]-3-(3,5-dimethylphenyl)propanoic acid Chemical compound CC1=CC(C)=CC([C@H](CC(O)=O)NC(=O)NC=2C(N(CC=3C(=CC=CC=3)Cl)C=CC=2)=O)=C1 DSNCZDYTKGBUMO-NRFANRHFSA-N 0.000 description 1
• QZPYTXJBGAOIOP-IBGZPJMESA-N (3s)-3-[[1-[(2-chlorophenyl)methyl]-2-oxopyridin-3-yl]carbamoylamino]-3-(4-hydroxyphenyl)propanoic acid Chemical compound N([C@@H](CC(=O)O)C=1C=CC(O)=CC=1)C(=O)NC(C1=O)=CC=CN1CC1=CC=CC=C1Cl QZPYTXJBGAOIOP-IBGZPJMESA-N 0.000 description 1
• UAGPHZXJSPKAGC-FQEVSTJZSA-N (3s)-3-[[1-[(2-chlorophenyl)methyl]-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methoxy-3-methylphenyl)propanoic acid Chemical compound C1=C(C)C(OC)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=CC=CN1CC1=CC=CC=C1Cl UAGPHZXJSPKAGC-FQEVSTJZSA-N 0.000 description 1
• PPPPJZYBYKRJGY-FQEVSTJZSA-N (3s)-3-[[1-[(2-chlorophenyl)methyl]-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methoxyphenyl)propanoic acid Chemical compound C1=CC(OC)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=CC=CN1CC1=CC=CC=C1Cl PPPPJZYBYKRJGY-FQEVSTJZSA-N 0.000 description 1
• GNCHCKVTNJDZDQ-QFIPXVFZSA-N (3s)-3-[[1-[(2-chlorophenyl)methyl]-4-(2,2-dimethylpropanoylamino)-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=C(NC(=O)C(C)(C)C)C=CN1CC1=CC=CC=C1Cl GNCHCKVTNJDZDQ-QFIPXVFZSA-N 0.000 description 1
• NFFRXLAVOWNYID-QHCPKHFHSA-N (3s)-3-[[1-[(2-chlorophenyl)methyl]-4-[2-(2-methoxyethoxy)ethoxy]-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound O=C1C(NC(=O)N[C@@H](CC(O)=O)C=2C=CC(C)=CC=2)=C(OCCOCCOC)C=CN1CC1=CC=CC=C1Cl NFFRXLAVOWNYID-QHCPKHFHSA-N 0.000 description 1
• WSLWESGKTWDDPU-NRFANRHFSA-N (3s)-3-[[1-[(2-chlorophenyl)methyl]-4-hydroxy-2-oxo-5-propylpyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound O=C1C(NC(=O)N[C@@H](CC(O)=O)C=2C=CC(C)=CC=2)=C(O)C(CCC)=CN1CC1=CC=CC=C1Cl WSLWESGKTWDDPU-NRFANRHFSA-N 0.000 description 1
• NOJGFYRCCNSGFU-SFHVURJKSA-N (3s)-3-[[1-[(2-chlorophenyl)methyl]-4-hydroxy-2-oxopyridin-3-yl]carbamoylamino]-3-(3,5-dimethoxy-4-methylphenyl)propanoic acid Chemical compound COC1=C(C)C(OC)=CC([C@H](CC(O)=O)NC(=O)NC=2C(N(CC=3C(=CC=CC=3)Cl)C=CC=2O)=O)=C1 NOJGFYRCCNSGFU-SFHVURJKSA-N 0.000 description 1
• IHYWGMKVZGRBOX-FQEVSTJZSA-N (3s)-3-[[1-[(2-chlorophenyl)methyl]-4-hydroxy-2-oxopyridin-3-yl]carbamoylamino]-3-(3-propoxyphenyl)propanoic acid Chemical compound CCCOC1=CC=CC([C@H](CC(O)=O)NC(=O)NC=2C(N(CC=3C(=CC=CC=3)Cl)C=CC=2O)=O)=C1 IHYWGMKVZGRBOX-FQEVSTJZSA-N 0.000 description 1
• DOUGOWNRENDINX-IBGZPJMESA-N (3s)-3-[[1-[(2-chlorophenyl)methyl]-4-hydroxy-2-oxopyridin-3-yl]carbamoylamino]-3-(4-ethoxyphenyl)propanoic acid Chemical compound C1=CC(OCC)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=C(O)C=CN1CC1=CC=CC=C1Cl DOUGOWNRENDINX-IBGZPJMESA-N 0.000 description 1
• LPMXAWSSWLCPMJ-SFHVURJKSA-N (3s)-3-[[1-[(2-chlorophenyl)methyl]-4-hydroxy-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=C(O)C=CN1CC1=CC=CC=C1Cl LPMXAWSSWLCPMJ-SFHVURJKSA-N 0.000 description 1
• VPUXZZJIKIIVKJ-NRFANRHFSA-N (3s)-3-[[1-[(2-chlorophenyl)methyl]-4-hydroxy-2-oxoquinolin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=C(O)C2=CC=CC=C2N1CC1=CC=CC=C1Cl VPUXZZJIKIIVKJ-NRFANRHFSA-N 0.000 description 1
• YKVNQFTUHZSROF-NRFANRHFSA-N (3s)-3-[[1-[(2-chlorophenyl)methyl]-4-hydroxy-5,6-dimethyl-2-oxopyridin-3-yl]carbamoylamino]-3-(3,4-diethoxyphenyl)propanoic acid Chemical compound C1=C(OCC)C(OCC)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=C(O)C(C)=C(C)N1CC1=CC=CC=C1Cl YKVNQFTUHZSROF-NRFANRHFSA-N 0.000 description 1
• AJZJNWQCAWBSAM-FQEVSTJZSA-N (3s)-3-[[1-[(2-chlorophenyl)methyl]-4-hydroxy-5-methyl-2-oxopyridin-3-yl]carbamoylamino]-3-(3-ethoxyphenyl)propanoic acid Chemical compound CCOC1=CC=CC([C@H](CC(O)=O)NC(=O)NC=2C(N(CC=3C(=CC=CC=3)Cl)C=C(C)C=2O)=O)=C1 AJZJNWQCAWBSAM-FQEVSTJZSA-N 0.000 description 1
• WGJZFXOBILLYRU-QFIPXVFZSA-N (3s)-3-[[1-[(2-chlorophenyl)methyl]-4-hydroxy-5-methyl-2-oxopyridin-3-yl]carbamoylamino]-3-[3-(diethylamino)phenyl]propanoic acid Chemical compound CCN(CC)C1=CC=CC([C@H](CC(O)=O)NC(=O)NC=2C(N(CC=3C(=CC=CC=3)Cl)C=C(C)C=2O)=O)=C1 WGJZFXOBILLYRU-QFIPXVFZSA-N 0.000 description 1
• FCRNFQMIFLZTMG-FQEVSTJZSA-N (3s)-3-[[1-[(2-chlorophenyl)methyl]-4-methyl-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=C(C)C=CN1CC1=CC=CC=C1Cl FCRNFQMIFLZTMG-FQEVSTJZSA-N 0.000 description 1
• OYTUBLSTEZLWSJ-IBGZPJMESA-N (3s)-3-[[1-[(2-chlorophenyl)methyl]-4-oxopyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C(C=C1)=O)=CN1CC1=CC=CC=C1Cl OYTUBLSTEZLWSJ-IBGZPJMESA-N 0.000 description 1
• CYFBQPIFFBZMQD-NRFANRHFSA-N (3s)-3-[[1-[(2-cyanophenyl)methyl]-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=CC=CN1CC1=CC=CC=C1C#N CYFBQPIFFBZMQD-NRFANRHFSA-N 0.000 description 1
• IKFWKNWZMBVMRO-FQEVSTJZSA-N (3s)-3-[[1-[(2-fluorophenyl)methyl]-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=CC=CN1CC1=CC=CC=C1F IKFWKNWZMBVMRO-FQEVSTJZSA-N 0.000 description 1
• XUJJROGREZNHLN-IBGZPJMESA-N (3s)-3-[[1-[(2-hydroxyphenyl)methyl]-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=CC=CN1CC1=CC=CC=C1O XUJJROGREZNHLN-IBGZPJMESA-N 0.000 description 1
• WIIKMLAQIFHUIL-FQEVSTJZSA-N (3s)-3-[[1-[(3-chlorophenyl)methyl]-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=CC=CN1CC1=CC=CC(Cl)=C1 WIIKMLAQIFHUIL-FQEVSTJZSA-N 0.000 description 1
• NZKLJTSFKVCQGA-FQEVSTJZSA-N (3s)-3-[[1-[(3-hydroxyphenyl)methyl]-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=CC=CN1CC1=CC=CC(O)=C1 NZKLJTSFKVCQGA-FQEVSTJZSA-N 0.000 description 1
• RZHCPDQCPNJXRO-QHCPKHFHSA-N (3s)-3-[[1-[(3-tert-butyl-2-methoxyphenyl)methyl]-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC=C(C(C)(C)C)C(OC)=C1CN1C(=O)C(NC(=O)N[C@@H](CC(O)=O)C=2C=CC(C)=CC=2)=CC=C1 RZHCPDQCPNJXRO-QHCPKHFHSA-N 0.000 description 1
• LUOOVATYANNXTC-FQEVSTJZSA-N (3s)-3-[[1-[(4-fluorophenyl)methyl]-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=CC=CN1CC1=CC=C(F)C=C1 LUOOVATYANNXTC-FQEVSTJZSA-N 0.000 description 1
• NDICCOQMGSZDLV-FQEVSTJZSA-N (3s)-3-[[1-[(5-chloro-2-fluorophenyl)methyl]-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=CC=CN1CC1=CC(Cl)=CC=C1F NDICCOQMGSZDLV-FQEVSTJZSA-N 0.000 description 1
• DWNVBXWUBUYHFX-IBGZPJMESA-N (3s)-3-[[1-[2-(2-hydroxyanilino)-2-oxoethyl]-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=CC=CN1CC(=O)NC1=CC=CC=C1O DWNVBXWUBUYHFX-IBGZPJMESA-N 0.000 description 1
• GFHXNEUBDHJXEC-FQEVSTJZSA-N (3s)-3-[[1-[[2-fluoro-4-(trifluoromethyl)phenyl]methyl]-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=CC=CN1CC1=CC=C(C(F)(F)F)C=C1F GFHXNEUBDHJXEC-FQEVSTJZSA-N 0.000 description 1
• DPVGJLKUPYHLOA-FQEVSTJZSA-N (3s)-3-[[2-[(2-chloro-6-ethoxyphenyl)methyl]-5-hydroxy-6-methyl-3-oxopyridazin-4-yl]carbamoylamino]-3-(3-ethoxyphenyl)propanoic acid Chemical compound CCOC1=CC=CC([C@H](CC(O)=O)NC(=O)NC=2C(N(CC=3C(=CC=CC=3Cl)OCC)N=C(C)C=2O)=O)=C1 DPVGJLKUPYHLOA-FQEVSTJZSA-N 0.000 description 1
• HAYHNFYXEYIOQG-KRWDZBQOSA-N (3s)-3-[[2-oxo-1-(thiophen-2-ylmethyl)pyridin-3-yl]carbamoylamino]-3-phenylpropanoic acid Chemical compound N([C@@H](CC(=O)O)C=1C=CC=CC=1)C(=O)NC(C1=O)=CC=CN1CC1=CC=CS1 HAYHNFYXEYIOQG-KRWDZBQOSA-N 0.000 description 1
• CTLOTPWYEKNWQQ-QFIPXVFZSA-N (3s)-3-[[4-(tert-butylamino)-1-[(2-chlorophenyl)methyl]-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=C(NC(C)(C)C)C=CN1CC1=CC=CC=C1Cl CTLOTPWYEKNWQQ-QFIPXVFZSA-N 0.000 description 1
• XNJBPXQBMAWTHQ-FQEVSTJZSA-N (3s)-3-[[4-amino-1-[(2-chlorophenyl)methyl]-6-methyl-2-oxopyridin-3-yl]carbamoylamino]-3-(4-methylphenyl)propanoic acid Chemical compound C1=CC(C)=CC=C1[C@H](CC(O)=O)NC(=O)NC(C1=O)=C(N)C=C(C)N1CC1=CC=CC=C1Cl XNJBPXQBMAWTHQ-FQEVSTJZSA-N 0.000 description 1
• YMVFJGSXZNNUDW-UHFFFAOYSA-N (4-chlorophenyl)methanamine Chemical compound NCC1=CC=C(Cl)C=C1 YMVFJGSXZNNUDW-UHFFFAOYSA-N 0.000 description 1
• STPKWKPURVSAJF-LJEWAXOPSA-N (4r,5r)-5-[4-[[4-(1-aza-4-azoniabicyclo[2.2.2]octan-4-ylmethyl)phenyl]methoxy]phenyl]-3,3-dibutyl-7-(dimethylamino)-1,1-dioxo-4,5-dihydro-2h-1$l^{6}-benzothiepin-4-ol Chemical compound O[C@H]1C(CCCC)(CCCC)CS(=O)(=O)C2=CC=C(N(C)C)C=C2[C@H]1C(C=C1)=CC=C1OCC(C=C1)=CC=C1C[N+]1(CC2)CCN2CC1 STPKWKPURVSAJF-LJEWAXOPSA-N 0.000 description 1
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
• JGAMOQYFDMQPRJ-GQCTYLIASA-N (e)-3-(dimethylamino)-2-methylprop-2-enal Chemical compound CN(C)\C=C(/C)C=O JGAMOQYFDMQPRJ-GQCTYLIASA-N 0.000 description 1
• SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
• 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 description 1
• 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 description 1
• 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 description 1
• XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical group [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 description 1
• 229940058015 1,3-butylene glycol Drugs 0.000 description 1
• KKHFRAFPESRGGD-UHFFFAOYSA-N 1,3-dimethyl-7-[3-(n-methylanilino)propyl]purine-2,6-dione Chemical compound C1=NC=2N(C)C(=O)N(C)C(=O)C=2N1CCCN(C)C1=CC=CC=C1 KKHFRAFPESRGGD-UHFFFAOYSA-N 0.000 description 1
• ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 1
• PURSZYWBIQIANP-UHFFFAOYSA-N 1-(bromomethyl)-2-chlorobenzene Chemical compound ClC1=CC=CC=C1CBr PURSZYWBIQIANP-UHFFFAOYSA-N 0.000 description 1
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 1
• UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 1
• QXOGPTXQGKQSJT-UHFFFAOYSA-N 1-amino-4-[4-(3,4-dimethylphenyl)sulfanylanilino]-9,10-dioxoanthracene-2-sulfonic acid Chemical compound Cc1ccc(Sc2ccc(Nc3cc(c(N)c4C(=O)c5ccccc5C(=O)c34)S(O)(=O)=O)cc2)cc1C QXOGPTXQGKQSJT-UHFFFAOYSA-N 0.000 description 1
• HNMYSCABMYNGTP-UHFFFAOYSA-N 1-chloro-3-ethoxybenzene Chemical compound CCOC1=CC=CC(Cl)=C1 HNMYSCABMYNGTP-UHFFFAOYSA-N 0.000 description 1
• VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical class CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
• VUQPJRPDRDVQMN-UHFFFAOYSA-N 1-chlorooctadecane Chemical class CCCCCCCCCCCCCCCCCCCl VUQPJRPDRDVQMN-UHFFFAOYSA-N 0.000 description 1
• 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
• 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
• YSFQIJDACSFIOH-UHFFFAOYSA-N 2,2-diaminopropanoic acid Chemical compound CC(N)(N)C(O)=O YSFQIJDACSFIOH-UHFFFAOYSA-N 0.000 description 1
• JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
• NUMXHEUHHRTBQT-AATRIKPKSA-N 2,4-dimethoxy-1-[(e)-2-nitroethenyl]benzene Chemical compound COC1=CC=C(\C=C\[N+]([O-])=O)C(OC)=C1 NUMXHEUHHRTBQT-AATRIKPKSA-N 0.000 description 1
• 125000006508 2,6-difluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C(F)=C1[H])C([H])([H])* 0.000 description 1
• GLDCXBNBWBSNON-UHFFFAOYSA-N 2-(2-ethoxyphenyl)propanoic acid Chemical compound CCOC1=CC=CC=C1C(C)C(O)=O GLDCXBNBWBSNON-UHFFFAOYSA-N 0.000 description 1
• YCWRFIYBUQBHJI-UHFFFAOYSA-N 2-(4-aminophenyl)acetonitrile Chemical group NC1=CC=C(CC#N)C=C1 YCWRFIYBUQBHJI-UHFFFAOYSA-N 0.000 description 1
• JPMRGPPMXHGKRO-UHFFFAOYSA-N 2-(chloromethyl)pyridine hydrochloride Chemical compound Cl.ClCC1=CC=CC=N1 JPMRGPPMXHGKRO-UHFFFAOYSA-N 0.000 description 1
• MUXUAHSVTHNEHG-UHFFFAOYSA-N 2-[(2,4-dioxo-3h-[1,3]oxazolo[4,5-c]pyridin-5-yl)methyl]benzonitrile Chemical compound O1C(=O)NC(C2=O)=C1C=CN2CC1=CC=CC=C1C#N MUXUAHSVTHNEHG-UHFFFAOYSA-N 0.000 description 1
• ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 description 1
• PYRKKGOKRMZEIT-UHFFFAOYSA-N 2-[6-(2-cyclopropylethoxy)-9-(2-hydroxy-2-methylpropyl)-1h-phenanthro[9,10-d]imidazol-2-yl]-5-fluorobenzene-1,3-dicarbonitrile Chemical compound C1=C2C3=CC(CC(C)(O)C)=CC=C3C=3NC(C=4C(=CC(F)=CC=4C#N)C#N)=NC=3C2=CC=C1OCCC1CC1 PYRKKGOKRMZEIT-UHFFFAOYSA-N 0.000 description 1
• VVCMGAUPZIKYTH-VGHSCWAPSA-N 2-acetyloxybenzoic acid;[(2s,3r)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl] propanoate;1,3,7-trimethylpurine-2,6-dione Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O.CN1C(=O)N(C)C(=O)C2=C1N=CN2C.C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 VVCMGAUPZIKYTH-VGHSCWAPSA-N 0.000 description 1
• GTIGRJZUYOJHBN-UHFFFAOYSA-N 2-amino-3-(3,4-diethoxyphenyl)propanoic acid Chemical compound CCOC1=CC=C(CC(N)C(O)=O)C=C1OCC GTIGRJZUYOJHBN-UHFFFAOYSA-N 0.000 description 1
• SEYVYCRBBASCRX-UHFFFAOYSA-N 2-amino-3-(3-ethoxyphenyl)propanoic acid Chemical compound CCOC1=CC=CC(CC(N)C(O)=O)=C1 SEYVYCRBBASCRX-UHFFFAOYSA-N 0.000 description 1
• WDJVWHLCJWZVON-UHFFFAOYSA-N 2-amino-3-(6-methoxynaphthalen-2-yl)propanoic acid Chemical compound C1=C(CC(N)C(O)=O)C=CC2=CC(OC)=CC=C21 WDJVWHLCJWZVON-UHFFFAOYSA-N 0.000 description 1
• JZRBSTONIYRNRI-UHFFFAOYSA-N 2-azaniumyl-3-(3-methylphenyl)propanoate Chemical compound CC1=CC=CC(CC(N)C(O)=O)=C1 JZRBSTONIYRNRI-UHFFFAOYSA-N 0.000 description 1
• ZAMOVMHWSVVCQD-UHFFFAOYSA-N 2-benzyl-3-chlorophenol Chemical compound OC1=CC=CC(Cl)=C1CC1=CC=CC=C1 ZAMOVMHWSVVCQD-UHFFFAOYSA-N 0.000 description 1
• 125000006280 2-bromobenzyl group Chemical group [H]C1=C([H])C(Br)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
• XPTAYRHLHAFUOS-UHFFFAOYSA-N 2-chloro-6-fluorobenzonitrile Chemical compound FC1=CC=CC(Cl)=C1C#N XPTAYRHLHAFUOS-UHFFFAOYSA-N 0.000 description 1
• 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
• MGOLNIXAPIAKFM-UHFFFAOYSA-N 2-isocyanato-2-methylpropane Chemical compound CC(C)(C)N=C=O MGOLNIXAPIAKFM-UHFFFAOYSA-N 0.000 description 1
• IEEHKTFVUIVORU-UHFFFAOYSA-N 2-methylpropanedioyl dichloride Chemical compound ClC(=O)C(C)C(Cl)=O IEEHKTFVUIVORU-UHFFFAOYSA-N 0.000 description 1
• YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 1
• 229940080296 2-naphthalenesulfonate Drugs 0.000 description 1
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
• WMPPDTMATNBGJN-UHFFFAOYSA-N 2-phenylethylbromide Chemical class BrCCC1=CC=CC=C1 WMPPDTMATNBGJN-UHFFFAOYSA-N 0.000 description 1
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
• 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 description 1
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
• PXRUYRQDSKNRJE-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-2,2-difluoro-3-[[2-oxo-1-(thiophen-2-ylmethyl)pyridin-3-yl]carbamoylamino]propanoic acid Chemical compound C=1C=C2OCOC2=CC=1C(C(F)(F)C(=O)O)NC(=O)NC(C1=O)=CC=CN1CC1=CC=CS1 PXRUYRQDSKNRJE-UHFFFAOYSA-N 0.000 description 1
• LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 1
• RLDZLBKVTQRJLN-UHFFFAOYSA-N 3-(3-chlorophenyl)-3-[[1-[(2-chlorophenyl)methyl]-2-oxopyridin-3-yl]carbamoylamino]propanoic acid Chemical compound C=1C=CC(Cl)=CC=1C(CC(=O)O)NC(=O)NC(C1=O)=CC=CN1CC1=CC=CC=C1Cl RLDZLBKVTQRJLN-UHFFFAOYSA-N 0.000 description 1
• OURRJSFDZKJPSN-UHFFFAOYSA-N 3-(3-chlorophenyl)-3-[[1-[(2-chlorophenyl)methyl]-4-hydroxy-2-oxopyridin-3-yl]carbamoylamino]propanoic acid Chemical compound C=1C=CC(Cl)=CC=1C(CC(=O)O)NC(=O)NC(C1=O)=C(O)C=CN1CC1=CC=CC=C1Cl OURRJSFDZKJPSN-UHFFFAOYSA-N 0.000 description 1
• VWXVTHDQAOAENP-UHFFFAOYSA-N 3-(3-methylphenyl)propanoic acid Chemical compound CC1=CC=CC(CCC(O)=O)=C1 VWXVTHDQAOAENP-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
• WFOVEDJTASPCIR-UHFFFAOYSA-N 3-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)methylamino]-n-[[2-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1CNC(C=1)=CC=CC=1C(=O)NCC1=CC=CC=C1C(F)(F)F WFOVEDJTASPCIR-UHFFFAOYSA-N 0.000 description 1
• QEPSTMIWXGNAPI-UHFFFAOYSA-N 3-[[1-[(2-chlorophenyl)methyl]-2-oxopyridin-3-yl]carbamoylamino]-3-(3,4-dichlorophenyl)propanoic acid Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(CC(=O)O)NC(=O)NC(C1=O)=CC=CN1CC1=CC=CC=C1Cl QEPSTMIWXGNAPI-UHFFFAOYSA-N 0.000 description 1
• UUKIBUXWKXFKLI-UHFFFAOYSA-N 3-[[1-[(2-chlorophenyl)methyl]-4-hydroxy-2-oxopyridin-3-yl]carbamoylamino]-3-naphthalen-2-ylpropanoic acid Chemical compound C=1C=C2C=CC=CC2=CC=1C(CC(=O)O)NC(=O)NC(C1=O)=C(O)C=CN1CC1=CC=CC=C1Cl UUKIBUXWKXFKLI-UHFFFAOYSA-N 0.000 description 1
• GTYRFVGHYNRSKT-UHFFFAOYSA-N 3-benzylpyrrole-2,5-dione Chemical compound O=C1NC(=O)C(CC=2C=CC=CC=2)=C1 GTYRFVGHYNRSKT-UHFFFAOYSA-N 0.000 description 1
• SUISZCALMBHJQX-UHFFFAOYSA-N 3-bromobenzaldehyde Chemical compound BrC1=CC=CC(C=O)=C1 SUISZCALMBHJQX-UHFFFAOYSA-N 0.000 description 1
• 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 description 1
• XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 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
• CZAWIHJWRJIMSE-UHFFFAOYSA-N 4-[(2,4-dioxo-3h-[1,3]oxazolo[4,5-c]pyridin-5-yl)methyl]-n,n-dimethylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N(C)C)=CC=C1CN1C(=O)C(NC(=O)O2)=C2C=C1 CZAWIHJWRJIMSE-UHFFFAOYSA-N 0.000 description 1
• GSDQYSSLIKJJOG-UHFFFAOYSA-N 4-chloro-2-(3-chloroanilino)benzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1NC1=CC=CC(Cl)=C1 GSDQYSSLIKJJOG-UHFFFAOYSA-N 0.000 description 1
• DQAZPZIYEOGZAF-UHFFFAOYSA-N 4-ethyl-n-[4-(3-ethynylanilino)-7-methoxyquinazolin-6-yl]piperazine-1-carboxamide Chemical compound C1CN(CC)CCN1C(=O)NC(C(=CC1=NC=N2)OC)=CC1=C2NC1=CC=CC(C#C)=C1 DQAZPZIYEOGZAF-UHFFFAOYSA-N 0.000 description 1
• 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 1
• FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
• 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
• 125000002471 4H-quinolizinyl group Chemical group C=1(C=CCN2C=CC=CC12)* 0.000 description 1
• IFBSLYGVHHCCPU-UHFFFAOYSA-N 5-[(2,4,6-trimethylphenyl)methyl]-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound CC1=CC(C)=CC(C)=C1CN1C(=O)C(NC(=O)O2)=C2C=C1 IFBSLYGVHHCCPU-UHFFFAOYSA-N 0.000 description 1
• HSMUOJYMOIPMJH-UHFFFAOYSA-N 5-[(2,4-dichlorophenyl)methyl]-7-methyl-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound O=C1C=2NC(=O)OC=2C(C)=CN1CC1=CC=C(Cl)C=C1Cl HSMUOJYMOIPMJH-UHFFFAOYSA-N 0.000 description 1
• YCROZHHKJRMEQY-UHFFFAOYSA-N 5-[(2,6-difluorophenyl)methyl]-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound FC1=CC=CC(F)=C1CN1C(=O)C(NC(=O)O2)=C2C=C1 YCROZHHKJRMEQY-UHFFFAOYSA-N 0.000 description 1
• VHUXKMDBWITRST-UHFFFAOYSA-N 5-[(2,6-difluorophenyl)methyl]-7-methyl-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound O=C1C=2NC(=O)OC=2C(C)=CN1CC1=C(F)C=CC=C1F VHUXKMDBWITRST-UHFFFAOYSA-N 0.000 description 1
• KOPAGUQKSSEYMM-UHFFFAOYSA-N 5-[(2-chloro-5-ethoxyphenyl)methyl]-7-methyl-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound CCOC1=CC=C(Cl)C(CN2C(C=3NC(=O)OC=3C(C)=C2)=O)=C1 KOPAGUQKSSEYMM-UHFFFAOYSA-N 0.000 description 1
• QDMAGZQORXHWRQ-UHFFFAOYSA-N 5-[(2-chloro-5-fluorophenyl)methyl]-7-methyl-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound O=C1C=2NC(=O)OC=2C(C)=CN1CC1=CC(F)=CC=C1Cl QDMAGZQORXHWRQ-UHFFFAOYSA-N 0.000 description 1
• JTPLQRLQOPAZRM-UHFFFAOYSA-N 5-[(2-chloro-5-methoxyphenyl)methyl]-1,3-oxazolidine Chemical compound ClC1=C(CC2CNCO2)C=C(C=C1)OC JTPLQRLQOPAZRM-UHFFFAOYSA-N 0.000 description 1
• FPNKCVXUTGFJDH-UHFFFAOYSA-N 5-[(2-chloro-5-methylsulfanylphenyl)methyl]-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound CSC1=CC=C(Cl)C(CN2C(C=3NC(=O)OC=3C=C2)=O)=C1 FPNKCVXUTGFJDH-UHFFFAOYSA-N 0.000 description 1
• DCMPRDQJQNULGN-UHFFFAOYSA-N 5-[(2-chloro-5-propoxyphenyl)methyl]-7-methyl-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound CCCOC1=CC=C(Cl)C(CN2C(C=3NC(=O)OC=3C(C)=C2)=O)=C1 DCMPRDQJQNULGN-UHFFFAOYSA-N 0.000 description 1
• SJWUCQAGEXAEBF-UHFFFAOYSA-N 5-[(2-chloro-6-ethoxyphenyl)methyl]-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound CCOC1=CC=CC(Cl)=C1CN1C(=O)C(NC(=O)O2)=C2C=C1 SJWUCQAGEXAEBF-UHFFFAOYSA-N 0.000 description 1
• RNAXAGLZFQQOIG-UHFFFAOYSA-N 5-[(2-chloro-6-ethoxyphenyl)methyl]-6,7-dimethyl-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound CCOC1=CC=CC(Cl)=C1CN1C(=O)C(NC(=O)O2)=C2C(C)=C1C RNAXAGLZFQQOIG-UHFFFAOYSA-N 0.000 description 1
• SFJNEEUNLGIYKI-UHFFFAOYSA-N 5-[(2-chloro-6-ethoxyphenyl)methyl]-6-methyl-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound CCOC1=CC=CC(Cl)=C1CN1C(=O)C(NC(=O)O2)=C2C=C1C SFJNEEUNLGIYKI-UHFFFAOYSA-N 0.000 description 1
• YZLOPWUIABNCMP-UHFFFAOYSA-N 5-[(2-chloro-6-ethoxyphenyl)methyl]-7-cyclopropyl-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound CCOC1=CC=CC(Cl)=C1CN1C(=O)C(NC(=O)O2)=C2C(C2CC2)=C1 YZLOPWUIABNCMP-UHFFFAOYSA-N 0.000 description 1
• MWKXRVIHUBFQOD-UHFFFAOYSA-N 5-[(2-chloro-6-ethoxyphenyl)methyl]-7-ethyl-6-methyl-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound CCOC1=CC=CC(Cl)=C1CN1C(=O)C(NC(=O)O2)=C2C(CC)=C1C MWKXRVIHUBFQOD-UHFFFAOYSA-N 0.000 description 1
• ILOHFVNHDNGYMV-UHFFFAOYSA-N 5-[(2-chloro-6-methylphenyl)methyl]-6,7-dimethyl-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound CC1=CC=CC(Cl)=C1CN1C(=O)C(NC(=O)O2)=C2C(C)=C1C ILOHFVNHDNGYMV-UHFFFAOYSA-N 0.000 description 1
• XWISGBGFECWNIY-UHFFFAOYSA-N 5-[(2-chloro-6-methylphenyl)methyl]-7-methyl-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound CC1=CC=CC(Cl)=C1CN1C(=O)C(NC(=O)O2)=C2C(C)=C1 XWISGBGFECWNIY-UHFFFAOYSA-N 0.000 description 1
• UJISBSJFVCRKEQ-UHFFFAOYSA-N 5-[(2-chloro-6-propan-2-yloxyphenyl)methyl]-7-methyl-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound CC(C)OC1=CC=CC(Cl)=C1CN1C(=O)C(NC(=O)O2)=C2C(C)=C1 UJISBSJFVCRKEQ-UHFFFAOYSA-N 0.000 description 1
• UNAIEFPGOHRNAF-UHFFFAOYSA-N 5-[(2-chlorophenyl)methyl]-6,7-dimethyl-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound CC1=C(C)C=2OC(=O)NC=2C(=O)N1CC1=CC=CC=C1Cl UNAIEFPGOHRNAF-UHFFFAOYSA-N 0.000 description 1
• MMCUVKQCTJAZJW-UHFFFAOYSA-N 5-[(2-chlorophenyl)methyl]-7-cyclopropyl-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound ClC1=CC=CC=C1CN1C(=O)C(NC(=O)O2)=C2C(C2CC2)=C1 MMCUVKQCTJAZJW-UHFFFAOYSA-N 0.000 description 1
• ANWMGNVYDBWLMQ-UHFFFAOYSA-N 5-[(2-chlorophenyl)methyl]-7-ethyl-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound O=C1C=2NC(=O)OC=2C(CC)=CN1CC1=CC=CC=C1Cl ANWMGNVYDBWLMQ-UHFFFAOYSA-N 0.000 description 1
• LRRGOCDSFNDZSN-UHFFFAOYSA-N 5-[(2-fluoro-6-methoxyphenyl)methyl]-7-methyl-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound COC1=CC=CC(F)=C1CN1C(=O)C(NC(=O)O2)=C2C(C)=C1 LRRGOCDSFNDZSN-UHFFFAOYSA-N 0.000 description 1
• KEXXVEYSOZJEJX-UHFFFAOYSA-N 5-[(2-methylphenyl)methyl]-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound CC1=CC=CC=C1CN1C(=O)C(NC(=O)O2)=C2C=C1 KEXXVEYSOZJEJX-UHFFFAOYSA-N 0.000 description 1
• RKRBKMVMIZUFQM-UHFFFAOYSA-N 5-[(2-methylsulfanylphenyl)methyl]-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound CSC1=CC=CC=C1CN1C(=O)C(NC(=O)O2)=C2C=C1 RKRBKMVMIZUFQM-UHFFFAOYSA-N 0.000 description 1
• FTZPCUHFDGBXNK-UHFFFAOYSA-N 5-[(3,4-dichlorophenyl)methyl]-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound C1=C(Cl)C(Cl)=CC=C1CN1C(=O)C(NC(=O)O2)=C2C=C1 FTZPCUHFDGBXNK-UHFFFAOYSA-N 0.000 description 1
• UMVITHYZKHTDFX-UHFFFAOYSA-N 5-[(3-methoxyphenyl)methyl]-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound COC1=CC=CC(CN2C(C=3NC(=O)OC=3C=C2)=O)=C1 UMVITHYZKHTDFX-UHFFFAOYSA-N 0.000 description 1
• JISRCOPIASBVLB-UHFFFAOYSA-N 5-[(3-methylsulfanylphenyl)methyl]-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound CSC1=CC=CC(CN2C(C=3NC(=O)OC=3C=C2)=O)=C1 JISRCOPIASBVLB-UHFFFAOYSA-N 0.000 description 1
• ZQYWXEFLHULFFY-UHFFFAOYSA-N 5-[(3-methylsulfonylphenyl)methyl]-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound CS(=O)(=O)C1=CC=CC(CN2C(C=3NC(=O)OC=3C=C2)=O)=C1 ZQYWXEFLHULFFY-UHFFFAOYSA-N 0.000 description 1
• JOXFCWDMVPBRNO-UHFFFAOYSA-N 5-[(4-chlorophenyl)methyl]-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound C1=CC(Cl)=CC=C1CN1C(=O)C(NC(=O)O2)=C2C=C1 JOXFCWDMVPBRNO-UHFFFAOYSA-N 0.000 description 1
• XHRNVFOTKLULNZ-UHFFFAOYSA-N 5-[(4-chlorophenyl)methyl]-7-methyl-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound O=C1C=2NC(=O)OC=2C(C)=CN1CC1=CC=C(Cl)C=C1 XHRNVFOTKLULNZ-UHFFFAOYSA-N 0.000 description 1
• DASHVJCSHAZIPR-UHFFFAOYSA-N 5-[(4-chlorophenyl)methyl]-7-propyl-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound O=C1C=2NC(=O)OC=2C(CCC)=CN1CC1=CC=C(Cl)C=C1 DASHVJCSHAZIPR-UHFFFAOYSA-N 0.000 description 1
• GOECSMRYWUPFFB-UHFFFAOYSA-N 5-[(4-methoxyphenyl)methyl]-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound C1=CC(OC)=CC=C1CN1C(=O)C(NC(=O)O2)=C2C=C1 GOECSMRYWUPFFB-UHFFFAOYSA-N 0.000 description 1
• LMXGXFQJWWQXOK-UHFFFAOYSA-N 5-[(4-tert-butylphenyl)methyl]-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound C1=CC(C(C)(C)C)=CC=C1CN1C(=O)C(NC(=O)O2)=C2C=C1 LMXGXFQJWWQXOK-UHFFFAOYSA-N 0.000 description 1
• AZMUBMZPGOPROA-UHFFFAOYSA-N 5-[(5-acetyl-2-methoxyphenyl)methyl]-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound COC1=CC=C(C(C)=O)C=C1CN1C(=O)C(NC(=O)O2)=C2C=C1 AZMUBMZPGOPROA-UHFFFAOYSA-N 0.000 description 1
• FZQYQFJPBKFVJV-UHFFFAOYSA-N 5-[(5-chloro-2-fluorophenyl)methyl]-7-methyl-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound O=C1C=2NC(=O)OC=2C(C)=CN1CC1=CC(Cl)=CC=C1F FZQYQFJPBKFVJV-UHFFFAOYSA-N 0.000 description 1
• JADXMNFGESSROC-UHFFFAOYSA-N 5-[(5-fluoro-2-methylphenyl)methyl]-7-methyl-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound CC1=CC=C(F)C=C1CN1C(=O)C(NC(=O)O2)=C2C(C)=C1 JADXMNFGESSROC-UHFFFAOYSA-N 0.000 description 1
• FOMUFFOGEPPROO-UHFFFAOYSA-N 5-[[2-(trifluoromethoxy)phenyl]methyl]-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound FC(F)(F)OC1=CC=CC=C1CN1C(=O)C(NC(=O)O2)=C2C=C1 FOMUFFOGEPPROO-UHFFFAOYSA-N 0.000 description 1
• FGDMQKJXXJGDDK-UHFFFAOYSA-N 5-[[2-chloro-5-(trifluoromethyl)phenyl]methyl]-7-methyl-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound O=C1C=2NC(=O)OC=2C(C)=CN1CC1=CC(C(F)(F)F)=CC=C1Cl FGDMQKJXXJGDDK-UHFFFAOYSA-N 0.000 description 1
• GYFGSRNUYRHPGP-UHFFFAOYSA-N 5-[[2-chloro-6-(2,2,2-trifluoroethoxy)phenyl]methyl]-7-methyl-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound O=C1C=2NC(=O)OC=2C(C)=CN1CC1=C(Cl)C=CC=C1OCC(F)(F)F GYFGSRNUYRHPGP-UHFFFAOYSA-N 0.000 description 1
• NBHBVVYDTMFILW-UHFFFAOYSA-N 5-[[2-chloro-6-(2-methylpropoxy)phenyl]methyl]-7-methyl-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound CC(C)COC1=CC=CC(Cl)=C1CN1C(=O)C(NC(=O)O2)=C2C(C)=C1 NBHBVVYDTMFILW-UHFFFAOYSA-N 0.000 description 1
• UUXUBVICEPUADJ-UHFFFAOYSA-N 5-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-7-methyl-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound O=C1C=2NC(=O)OC=2C(C)=CN1CC1=C(F)C=CC=C1C(F)(F)F UUXUBVICEPUADJ-UHFFFAOYSA-N 0.000 description 1
• IHMJUNFHKBBHSS-UHFFFAOYSA-N 5-[[3-(trifluoromethyl)phenyl]methyl]-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound FC(F)(F)C1=CC=CC(CN2C(C=3NC(=O)OC=3C=C2)=O)=C1 IHMJUNFHKBBHSS-UHFFFAOYSA-N 0.000 description 1
• VJIMPARYEDYYSX-UHFFFAOYSA-N 5-[[4-(trifluoromethyl)phenyl]methyl]-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound C1=CC(C(F)(F)F)=CC=C1CN1C(=O)C(NC(=O)O2)=C2C=C1 VJIMPARYEDYYSX-UHFFFAOYSA-N 0.000 description 1
• NGLSRQWOZPGYCA-UHFFFAOYSA-N 5-benzyl-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound O1C(=O)NC(C2=O)=C1C=CN2CC1=CC=CC=C1 NGLSRQWOZPGYCA-UHFFFAOYSA-N 0.000 description 1
• PENMOQZDNRRAQK-UHFFFAOYSA-N 5-benzyl-6-methyl-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound CC1=CC=2OC(=O)NC=2C(=O)N1CC1=CC=CC=C1 PENMOQZDNRRAQK-UHFFFAOYSA-N 0.000 description 1
• 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 description 1
• 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 1
• MJQAAEHTCMTXQL-UHFFFAOYSA-N 7-butyl-5-[(2-chlorophenyl)methyl]-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound O=C1C=2NC(=O)OC=2C(CCCC)=CN1CC1=CC=CC=C1Cl MJQAAEHTCMTXQL-UHFFFAOYSA-N 0.000 description 1
• YJZZBZLYCLMZAM-UHFFFAOYSA-N 7-methyl-5-[(4-methylsulfonylphenyl)methyl]-3h-[1,3]oxazolo[4,5-c]pyridine-2,4-dione Chemical compound O=C1C=2NC(=O)OC=2C(C)=CN1CC1=CC=C(S(C)(=O)=O)C=C1 YJZZBZLYCLMZAM-UHFFFAOYSA-N 0.000 description 1
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
• 235000017060 Arachis glabrata Nutrition 0.000 description 1
• 244000105624 Arachis hypogaea Species 0.000 description 1
• 235000010777 Arachis hypogaea Nutrition 0.000 description 1
• 235000018262 Arachis monticola Nutrition 0.000 description 1
• 239000005711 Benzoic acid Substances 0.000 description 1
• 239000004342 Benzoyl peroxide Substances 0.000 description 1
• OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
• FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
• JQUCWIWWWKZNCS-LESHARBVSA-N C(C1=CC=CC=C1)(=O)NC=1SC[C@H]2[C@@](N1)(CO[C@H](C2)C)C=2SC=C(N2)NC(=O)C2=NC=C(C=C2)OC(F)F Chemical compound C(C1=CC=CC=C1)(=O)NC=1SC[C@H]2[C@@](N1)(CO[C@H](C2)C)C=2SC=C(N2)NC(=O)C2=NC=C(C=C2)OC(F)F JQUCWIWWWKZNCS-LESHARBVSA-N 0.000 description 1
• YTEMNAKRHMBJJS-UHFFFAOYSA-N CC(C(O)=O)C1=CC=C(CC=C2)C2=C1 Chemical compound CC(C(O)=O)C1=CC=C(CC=C2)C2=C1 YTEMNAKRHMBJJS-UHFFFAOYSA-N 0.000 description 1
• UOVUIFYEGJENBC-UHFFFAOYSA-N CC1=CC(=C(C(=C1)C)CN2C3=C(C=CNC3=O)OC2=O)C Chemical compound CC1=CC(=C(C(=C1)C)CN2C3=C(C=CNC3=O)OC2=O)C UOVUIFYEGJENBC-UHFFFAOYSA-N 0.000 description 1
• PHFVDIUTRCKCGS-RZQQEOIVSA-N CC1=CC=C([C@H](CC([O-])=O)NC(NC2=CC=CN(CC3=CC=C[S+]3Cl)C2=O)=O)C=C1 Chemical compound CC1=CC=C([C@H](CC([O-])=O)NC(NC2=CC=CN(CC3=CC=C[S+]3Cl)C2=O)=O)C=C1 PHFVDIUTRCKCGS-RZQQEOIVSA-N 0.000 description 1
• UHNRLQRZRNKOKU-UHFFFAOYSA-N CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O Chemical compound CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O UHNRLQRZRNKOKU-UHFFFAOYSA-N 0.000 description 1
• XGRXMAYCKIVQFJ-NRFANRHFSA-N CC[C@@H](C1=CC=C(C=C1)C)NC(=O)NC2=C(C=CN(C2=O)CC3=C(C=CC(=C3)C)C)O Chemical compound CC[C@@H](C1=CC=C(C=C1)C)NC(=O)NC2=C(C=CN(C2=O)CC3=C(C=CC(=C3)C)C)O XGRXMAYCKIVQFJ-NRFANRHFSA-N 0.000 description 1
• 101100274581 Caenorhabditis elegans chc-1 gene Proteins 0.000 description 1
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
• 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
• 108010067225 Cell Adhesion Molecules Proteins 0.000 description 1
• 102000016289 Cell Adhesion Molecules Human genes 0.000 description 1
• KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
• PBMWKSYVBJRLHO-UHFFFAOYSA-N ClC1=CC=CC=C1CN1C(=O)C(NC(=O)O2)=C2C2=C1CCC2 Chemical compound ClC1=CC=CC=C1CN1C(=O)C(NC(=O)O2)=C2C2=C1CCC2 PBMWKSYVBJRLHO-UHFFFAOYSA-N 0.000 description 1
• 229940126639 Compound 33 Drugs 0.000 description 1
• 102000004127 Cytokines Human genes 0.000 description 1
• 108090000695 Cytokines Proteins 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
• CKLJMWTZIZZHCS-UHFFFAOYSA-N D-OH-Asp Natural products OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 description 1
• FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
• NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
• BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
• RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
• LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
• JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
• XXRCUYVCPSWGCC-UHFFFAOYSA-N Ethyl pyruvate Chemical compound CCOC(=O)C(C)=O XXRCUYVCPSWGCC-UHFFFAOYSA-N 0.000 description 1
• PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
• 108010037362 Extracellular Matrix Proteins Proteins 0.000 description 1
• 102000010834 Extracellular Matrix Proteins Human genes 0.000 description 1
• 239000004606 Fillers/Extenders Substances 0.000 description 1
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
• DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 1
• 239000004705 High-molecular-weight polyethylene Substances 0.000 description 1
• 101000939500 Homo sapiens UBX domain-containing protein 11 Proteins 0.000 description 1
• 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 1
• 241000692870 Inachis io Species 0.000 description 1
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
• 102000003777 Interleukin-1 beta Human genes 0.000 description 1
• 108090000193 Interleukin-1 beta Proteins 0.000 description 1
• 102000004388 Interleukin-4 Human genes 0.000 description 1
• 108090000978 Interleukin-4 Proteins 0.000 description 1
• 101710198693 Invasin Proteins 0.000 description 1
• CKLJMWTZIZZHCS-UWTATZPHSA-N L-Aspartic acid Natural products OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 description 1
• ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 1
• 239000004201 L-cysteine Substances 0.000 description 1
• 235000013878 L-cysteine Nutrition 0.000 description 1
• ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
• 229930182816 L-glutamine Natural products 0.000 description 1
• AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 description 1
• 229930182844 L-isoleucine Natural products 0.000 description 1
• ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 1
• AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 1
• JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
• 240000007472 Leucaena leucocephala Species 0.000 description 1
• 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
• 206010025323 Lymphomas Diseases 0.000 description 1
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
• PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 1
• 240000003183 Manihot esculenta Species 0.000 description 1
• 235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
• 229930195725 Mannitol Natural products 0.000 description 1
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
• 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
• BAVYZALUXZFZLV-UHFFFAOYSA-O Methylammonium ion Chemical compound [NH3+]C BAVYZALUXZFZLV-UHFFFAOYSA-O 0.000 description 1
• 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
• CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
• KAJBMCZQVSQJDE-YFKPBYRVSA-N Nalpha-(tert-butoxycarbonyl)-l-aspartic acid Chemical compound CC(C)(C)OC(=O)N[C@H](C(O)=O)CC(O)=O KAJBMCZQVSQJDE-YFKPBYRVSA-N 0.000 description 1
• PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
• 240000007817 Olea europaea Species 0.000 description 1
• 101150003085 Pdcl gene Proteins 0.000 description 1
• RFFFKMOABOFIDF-UHFFFAOYSA-N Pentanenitrile Chemical compound CCCCC#N RFFFKMOABOFIDF-UHFFFAOYSA-N 0.000 description 1
• 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
• 229920002732 Polyanhydride Polymers 0.000 description 1
• 229920001710 Polyorthoester Polymers 0.000 description 1
• 239000004793 Polystyrene Substances 0.000 description 1
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
• 235000004443 Ricinus communis Nutrition 0.000 description 1
• 206010039491 Sarcoma Diseases 0.000 description 1
• 229910004298 SiO 2 Inorganic materials 0.000 description 1
• PNUZDKCDAWUEGK-CYZMBNFOSA-N Sitafloxacin Chemical compound C([C@H]1N)N(C=2C(=C3C(C(C(C(O)=O)=CN3[C@H]3[C@H](C3)F)=O)=CC=2F)Cl)CC11CC1 PNUZDKCDAWUEGK-CYZMBNFOSA-N 0.000 description 1
• UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
• 244000061456 Solanum tuberosum Species 0.000 description 1
• 235000002595 Solanum tuberosum Nutrition 0.000 description 1
• SSZBUIDZHHWXNJ-UHFFFAOYSA-N Stearinsaeure-hexadecylester Natural products CCCCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCCCCCC SSZBUIDZHHWXNJ-UHFFFAOYSA-N 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
• 206010052779 Transplant rejections Diseases 0.000 description 1
• OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
• 206010054094 Tumour necrosis Diseases 0.000 description 1
• 102100029645 UBX domain-containing protein 11 Human genes 0.000 description 1
• 208000027418 Wounds and injury Diseases 0.000 description 1
• 240000008042 Zea mays Species 0.000 description 1
• 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
• 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
• ZATXVRSLQDRAHZ-UHFFFAOYSA-N [1,3]oxazolo[4,5-c]pyridine Chemical compound N1=CC=C2OC=NC2=C1 ZATXVRSLQDRAHZ-UHFFFAOYSA-N 0.000 description 1
• BFPLMTPHDFFMTG-UHFFFAOYSA-N [1,3]oxazolo[5,4-b]pyridine Chemical compound C1=CN=C2OC=NC2=C1 BFPLMTPHDFFMTG-UHFFFAOYSA-N 0.000 description 1
• CDXSJGDDABYYJV-UHFFFAOYSA-N acetic acid;ethanol Chemical compound CCO.CC(O)=O CDXSJGDDABYYJV-UHFFFAOYSA-N 0.000 description 1
• ZCHPKWUIAASXPV-UHFFFAOYSA-N acetic acid;methanol Chemical compound OC.CC(O)=O ZCHPKWUIAASXPV-UHFFFAOYSA-N 0.000 description 1
• WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
• 239000012346 acetyl chloride Substances 0.000 description 1
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
• 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
• 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
• 230000009471 action Effects 0.000 description 1
• 125000004423 acyloxy group Chemical group 0.000 description 1
• 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
• 230000001464 adherent effect Effects 0.000 description 1
• WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
• 239000003463 adsorbent Substances 0.000 description 1
• 229940072056 alginate Drugs 0.000 description 1
• 239000000783 alginic acid Substances 0.000 description 1
• 229960001126 alginic acid Drugs 0.000 description 1
• 150000004781 alginic acids Chemical class 0.000 description 1
• 229910052783 alkali metal Inorganic materials 0.000 description 1
• 150000001340 alkali metals Chemical class 0.000 description 1
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
• 125000005431 alkyl carboxamide group Chemical group 0.000 description 1
• 150000001350 alkyl halides Chemical class 0.000 description 1
• 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 description 1
• 125000004422 alkyl sulphonamide group Chemical group 0.000 description 1
• 125000005336 allyloxy group Chemical group 0.000 description 1
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-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
• AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 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
• 150000007854 aminals Chemical group 0.000 description 1
• 229910021529 ammonia Inorganic materials 0.000 description 1
• 239000000908 ammonium hydroxide Substances 0.000 description 1
• 150000008064 anhydrides Chemical class 0.000 description 1
• 150000001454 anthracenes Chemical class 0.000 description 1
• 239000003242 anti bacterial agent Substances 0.000 description 1
• 230000000844 anti-bacterial effect Effects 0.000 description 1
• 239000003429 antifungal agent Substances 0.000 description 1
• 229940121375 antifungal agent Drugs 0.000 description 1
• 239000008365 aqueous carrier Substances 0.000 description 1
• 239000012736 aqueous medium Substances 0.000 description 1
• 125000002102 aryl alkyloxo group Chemical group 0.000 description 1
• 125000005418 aryl aryl group Chemical group 0.000 description 1
• 125000004657 aryl sulfonyl amino group Chemical group 0.000 description 1
• 229960001230 asparagine Drugs 0.000 description 1
• 229940009098 aspartate Drugs 0.000 description 1
• 229960005261 aspartic acid Drugs 0.000 description 1
• 238000003556 assay Methods 0.000 description 1
• 238000010533 azeotropic distillation Methods 0.000 description 1
• 125000003725 azepanyl group Chemical group 0.000 description 1
• 125000003828 azulenyl group Chemical group 0.000 description 1
• 230000001580 bacterial effect Effects 0.000 description 1
• 229940077388 benzenesulfonate Drugs 0.000 description 1
• SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
• 229940050390 benzoate Drugs 0.000 description 1
• 235000010233 benzoic acid Nutrition 0.000 description 1
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 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
• 235000019400 benzoyl peroxide Nutrition 0.000 description 1
• 229960002903 benzyl benzoate Drugs 0.000 description 1
• AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-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
• XMIIGOLPHOKFCH-UHFFFAOYSA-N beta-phenylpropanoic acid Natural products OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 1
• 239000011230 binding agent Substances 0.000 description 1
• 235000010290 biphenyl Nutrition 0.000 description 1
• YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].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 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 1
• 210000004369 blood Anatomy 0.000 description 1
• 239000008280 blood Substances 0.000 description 1
• 210000004204 blood vessel Anatomy 0.000 description 1
• 230000037396 body weight Effects 0.000 description 1
• 229910000085 borane Inorganic materials 0.000 description 1
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
• 239000006172 buffering agent Substances 0.000 description 1
• HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
• 235000019437 butane-1,3-diol Nutrition 0.000 description 1
• BEWFIPLBFJGWSR-AONZOJHOSA-N butyl (z,12r)-12-acetyloxyoctadec-9-enoate Chemical group CCCCCC[C@@H](OC(C)=O)C\C=C/CCCCCCCC(=O)OCCCC BEWFIPLBFJGWSR-AONZOJHOSA-N 0.000 description 1
• 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 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
• 229910052792 caesium Inorganic materials 0.000 description 1
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
• 229910000024 caesium carbonate Inorganic materials 0.000 description 1
• BQRGNLJZBFXNCZ-UHFFFAOYSA-N calcein am Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC(CN(CC(=O)OCOC(C)=O)CC(=O)OCOC(C)=O)=C(OC(C)=O)C=C1OC1=C2C=C(CN(CC(=O)OCOC(C)=O)CC(=O)OCOC(=O)C)C(OC(C)=O)=C1 BQRGNLJZBFXNCZ-UHFFFAOYSA-N 0.000 description 1
• 239000011575 calcium Substances 0.000 description 1
• 229910052791 calcium Inorganic materials 0.000 description 1
• 229910000019 calcium carbonate Inorganic materials 0.000 description 1
• 235000010216 calcium carbonate Nutrition 0.000 description 1
• 239000001506 calcium phosphate Substances 0.000 description 1
• 229910000389 calcium phosphate Inorganic materials 0.000 description 1
• 235000011010 calcium phosphates Nutrition 0.000 description 1
• CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
• 239000008116 calcium stearate Substances 0.000 description 1
• 235000013539 calcium stearate Nutrition 0.000 description 1
• KXDHJXZQYSOELW-UHFFFAOYSA-N carbamic acid group Chemical group C(N)(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
• 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
• 125000002837 carbocyclic group Chemical group 0.000 description 1
• 150000001721 carbon Chemical group 0.000 description 1
• 125000005518 carboxamido group Chemical group 0.000 description 1
• 239000001768 carboxy methyl cellulose Substances 0.000 description 1
• 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
• 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
• 239000004359 castor oil Substances 0.000 description 1
• 150000001768 cations Chemical class 0.000 description 1
• 230000017455 cell-cell adhesion Effects 0.000 description 1
• 230000001413 cellular effect Effects 0.000 description 1
• 229960000541 cetyl alcohol Drugs 0.000 description 1
• 229910052801 chlorine Inorganic materials 0.000 description 1
• 229960004926 chlorobutanol Drugs 0.000 description 1
• 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
• 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
• 229940001468 citrate Drugs 0.000 description 1
• 235000015165 citric acid Nutrition 0.000 description 1
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid group Chemical class C(CC(O)(C(=O)O)CC(=O)O)(=O)O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
• 229940110456 cocoa butter Drugs 0.000 description 1
• 235000019868 cocoa butter Nutrition 0.000 description 1
• 239000002299 complementary DNA Substances 0.000 description 1
• 229940125797 compound 12 Drugs 0.000 description 1
• 229940125810 compound 20 Drugs 0.000 description 1
• 229940125807 compound 37 Drugs 0.000 description 1
• 238000001816 cooling Methods 0.000 description 1
• 235000005822 corn Nutrition 0.000 description 1
• 235000012343 cottonseed oil Nutrition 0.000 description 1
• 239000006071 cream Substances 0.000 description 1
• 239000013058 crude material Substances 0.000 description 1
• NXAKDBCNODQXBZ-YSZCVPRFSA-N cs1 peptide Chemical group C([C@@H](C(=O)NCC(=O)N1CCC[C@H]1C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](N)CC(O)=O)C(C)C)[C@@H](C)O)C1=CN=CN1 NXAKDBCNODQXBZ-YSZCVPRFSA-N 0.000 description 1
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
• 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
• 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
• 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
• ISQVBYGGNVVVHB-UHFFFAOYSA-N cyclopentylmethanol Chemical compound OCC1CCCC1 ISQVBYGGNVVVHB-UHFFFAOYSA-N 0.000 description 1
• 125000003493 decenyl group Chemical group [H]C([*])=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])[H] 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
• 125000005070 decynyl 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#C* 0.000 description 1
• 230000003111 delayed effect Effects 0.000 description 1
• 150000008050 dialkyl sulfates Chemical class 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
• 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
• HPNMFZURTQLUMO-UHFFFAOYSA-O diethylammonium Chemical compound CC[NH2+]CC HPNMFZURTQLUMO-UHFFFAOYSA-O 0.000 description 1
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 1
• UGMCXQCYOVCMTB-UHFFFAOYSA-K dihydroxy(stearato)aluminium Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[Al](O)O UGMCXQCYOVCMTB-UHFFFAOYSA-K 0.000 description 1
• SPCNPOWOBZQWJK-UHFFFAOYSA-N dimethoxy-(2-propan-2-ylsulfanylethylsulfanyl)-sulfanylidene-$l^{5}-phosphane Chemical compound COP(=S)(OC)SCCSC(C)C SPCNPOWOBZQWJK-UHFFFAOYSA-N 0.000 description 1
• SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
• GAFRWLVTHPVQGK-UHFFFAOYSA-N dipentyl sulfate Chemical class CCCCCOS(=O)(=O)OCCCCC GAFRWLVTHPVQGK-UHFFFAOYSA-N 0.000 description 1
• 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
• 239000002270 dispersing agent Substances 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
• 239000008298 dragée Substances 0.000 description 1
• 238000009510 drug design Methods 0.000 description 1
• 230000002500 effect on skin Effects 0.000 description 1
• 238000003821 enantio-separation Methods 0.000 description 1
• ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
• 210000003038 endothelium Anatomy 0.000 description 1
• 239000003623 enhancer Substances 0.000 description 1
• 150000002084 enol ethers Chemical class 0.000 description 1
• 239000002702 enteric coating Substances 0.000 description 1
• 238000009505 enteric coating Methods 0.000 description 1
• ZRSDQBKGDNPFLT-UHFFFAOYSA-N ethanol;oxolane Chemical compound CCO.C1CCOC1 ZRSDQBKGDNPFLT-UHFFFAOYSA-N 0.000 description 1
• KHDOTPVDSFBNMG-UHFFFAOYSA-N ethanol;pyridine Chemical compound CCO.C1=CC=NC=C1 KHDOTPVDSFBNMG-UHFFFAOYSA-N 0.000 description 1
• BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
• 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
• IRSJDVYTJUCXRV-UHFFFAOYSA-N ethyl 2-bromo-2,2-difluoroacetate Chemical compound CCOC(=O)C(F)(F)Br IRSJDVYTJUCXRV-UHFFFAOYSA-N 0.000 description 1
• JHZPNBKZPAWCJD-UHFFFAOYSA-N ethyl 2-oxocyclopentane-1-carboxylate Chemical compound CCOC(=O)C1CCCC1=O JHZPNBKZPAWCJD-UHFFFAOYSA-N 0.000 description 1
• WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 1
• LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
• 229940093471 ethyl oleate Drugs 0.000 description 1
• 229940117360 ethyl pyruvate Drugs 0.000 description 1
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
• 230000029142 excretion Effects 0.000 description 1
• 210000002744 extracellular matrix Anatomy 0.000 description 1
• 239000003885 eye ointment Substances 0.000 description 1
• 229930195729 fatty acid Natural products 0.000 description 1
• 239000000194 fatty acid Substances 0.000 description 1
• 239000000796 flavoring agent Substances 0.000 description 1
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
• 229910052731 fluorine Inorganic materials 0.000 description 1
• 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
• 235000013355 food flavoring agent Nutrition 0.000 description 1
• SAVROPQJUYSBDD-UHFFFAOYSA-N formyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)=CO SAVROPQJUYSBDD-UHFFFAOYSA-N 0.000 description 1
• 239000012458 free base Substances 0.000 description 1
• 125000000524 functional group Chemical group 0.000 description 1
• 210000001035 gastrointestinal tract Anatomy 0.000 description 1
• 239000000499 gel Substances 0.000 description 1
• 239000007903 gelatin capsule Substances 0.000 description 1
• 239000008103 glucose Substances 0.000 description 1
• 229960002989 glutamic acid Drugs 0.000 description 1
• YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
• SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
• JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
• 150000004820 halides Chemical class 0.000 description 1
• 230000035876 healing Effects 0.000 description 1
• 230000036541 health Effects 0.000 description 1
• 150000002373 hemiacetals Chemical group 0.000 description 1
• MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
• BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
• IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
• FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
• 125000005980 hexynyl group Chemical group 0.000 description 1
• 229960002885 histidine Drugs 0.000 description 1
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
• 230000007062 hydrolysis Effects 0.000 description 1
• 238000006460 hydrolysis reaction Methods 0.000 description 1
• XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
• 125000002883 imidazolyl group Chemical group 0.000 description 1
• 239000012535 impurity Substances 0.000 description 1
• 238000000338 in vitro Methods 0.000 description 1
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
• 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
• 125000006301 indolyl methyl group Chemical group 0.000 description 1
• 230000002757 inflammatory effect Effects 0.000 description 1
• 238000001802 infusion Methods 0.000 description 1
• 239000007972 injectable composition Substances 0.000 description 1
• 208000014674 injury Diseases 0.000 description 1
• 230000003993 interaction Effects 0.000 description 1
• 229940028885 interleukin-4 Drugs 0.000 description 1
• 238000007918 intramuscular administration Methods 0.000 description 1
• 238000010255 intramuscular injection Methods 0.000 description 1
• 239000007927 intramuscular injection Substances 0.000 description 1
• 238000007912 intraperitoneal administration Methods 0.000 description 1
• 238000001990 intravenous administration Methods 0.000 description 1
• 229910052740 iodine Inorganic materials 0.000 description 1
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
• SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
• 229960000310 isoleucine Drugs 0.000 description 1
• 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
• 239000007951 isotonicity adjuster Substances 0.000 description 1
• 125000000842 isoxazolyl group Chemical group 0.000 description 1
• 239000004922 lacquer Substances 0.000 description 1
• 239000000787 lecithin Substances 0.000 description 1
• 235000010445 lecithin Nutrition 0.000 description 1
• 239000003446 ligand Substances 0.000 description 1
• 239000004973 liquid crystal related substance Substances 0.000 description 1
• 239000006194 liquid suspension Substances 0.000 description 1
• 229910052744 lithium Inorganic materials 0.000 description 1
• DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
• CCZVEWRRAVASGL-UHFFFAOYSA-N lithium;2-methanidylpropane Chemical compound [Li+].CC(C)[CH2-] CCZVEWRRAVASGL-UHFFFAOYSA-N 0.000 description 1
• 239000000314 lubricant Substances 0.000 description 1
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
• 239000011777 magnesium Substances 0.000 description 1
• 229910052749 magnesium Inorganic materials 0.000 description 1
• 235000019359 magnesium stearate Nutrition 0.000 description 1
• 239000000594 mannitol Substances 0.000 description 1
• 235000010355 mannitol Nutrition 0.000 description 1
• 201000001441 melanoma Diseases 0.000 description 1
• 229940041616 menthol Drugs 0.000 description 1
• 125000005358 mercaptoalkyl group Chemical group 0.000 description 1
• 229910052751 metal Inorganic materials 0.000 description 1
• 239000002184 metal Substances 0.000 description 1
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
• GRWIABMEEKERFV-UHFFFAOYSA-N methanol;oxolane Chemical compound OC.C1CCOC1 GRWIABMEEKERFV-UHFFFAOYSA-N 0.000 description 1
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
• 239000004530 micro-emulsion Substances 0.000 description 1
• 229940016286 microcrystalline cellulose Drugs 0.000 description 1
• 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
• 239000008108 microcrystalline cellulose Substances 0.000 description 1
• 238000002156 mixing Methods 0.000 description 1
• 239000002808 molecular sieve Substances 0.000 description 1
• 125000002911 monocyclic heterocycle group Chemical group 0.000 description 1
• CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 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
• LPOIGVZLNWEGJG-UHFFFAOYSA-N n-benzyl-5-(4-methylpiperazin-1-yl)-2-nitroaniline Chemical compound C1CN(C)CCN1C1=CC=C([N+]([O-])=O)C(NCC=2C=CC=CC=2)=C1 LPOIGVZLNWEGJG-UHFFFAOYSA-N 0.000 description 1
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• CJYQZTZSYREQBD-UHFFFAOYSA-N n-fluorobenzenesulfonamide Chemical compound FNS(=O)(=O)C1=CC=CC=C1 CJYQZTZSYREQBD-UHFFFAOYSA-N 0.000 description 1
• SAVQQRYWWAGSQW-UHFFFAOYSA-N n-methyl-n-(trifluoro-$l^{4}-sulfanyl)methanamine Chemical compound CN(C)S(F)(F)F SAVQQRYWWAGSQW-UHFFFAOYSA-N 0.000 description 1
• SVDVKEBISAOWJT-UHFFFAOYSA-N n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC=C1 SVDVKEBISAOWJT-UHFFFAOYSA-N 0.000 description 1
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• KVBGVZZKJNLNJU-UHFFFAOYSA-M naphthalene-2-sulfonate Chemical compound C1=CC=CC2=CC(S(=O)(=O)[O-])=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-M 0.000 description 1
• 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
• 125000001624 naphthyl group Chemical group 0.000 description 1
• 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 description 1
• 239000007922 nasal spray Substances 0.000 description 1
• 229940097496 nasal spray Drugs 0.000 description 1
• 229940042880 natural phospholipid Drugs 0.000 description 1
• 235000001968 nicotinic acid Nutrition 0.000 description 1
• 239000011664 nicotinic acid Substances 0.000 description 1
• YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
• 229910017604 nitric acid Inorganic materials 0.000 description 1
• 231100000344 non-irritating Toxicity 0.000 description 1
• 239000012457 nonaqueous media Substances 0.000 description 1
• 231100000956 nontoxicity Toxicity 0.000 description 1
• 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
• 235000015097 nutrients Nutrition 0.000 description 1
• 239000002674 ointment Substances 0.000 description 1
• 235000008390 olive oil Nutrition 0.000 description 1
• 239000000668 oral spray Substances 0.000 description 1
• 229940041678 oral spray Drugs 0.000 description 1
• 150000002895 organic esters Chemical class 0.000 description 1
• 239000003960 organic solvent Substances 0.000 description 1
• 125000002971 oxazolyl group Chemical group 0.000 description 1
• 101710135378 pH 6 antigen Proteins 0.000 description 1
• YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
• 239000012188 paraffin wax Substances 0.000 description 1
• 239000002245 particle Substances 0.000 description 1
• 230000007170 pathology Effects 0.000 description 1
• 235000020232 peanut Nutrition 0.000 description 1
• 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
• PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 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
• 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
• 229960003742 phenol Drugs 0.000 description 1
• 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
• WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
• RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
• 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
• 150000003904 phospholipids Chemical class 0.000 description 1
• 125000005541 phosphonamide group Chemical group 0.000 description 1
• 235000011007 phosphoric acid Nutrition 0.000 description 1
• 150000003016 phosphoric acids Chemical class 0.000 description 1
• 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
• 229940075930 picrate Drugs 0.000 description 1
• OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
• 229940081310 piperonal Drugs 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
• 229920005862 polyol Polymers 0.000 description 1
• 150000003077 polyols Chemical class 0.000 description 1
• 229920002223 polystyrene Polymers 0.000 description 1
• IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 1
• 230000002335 preservative effect Effects 0.000 description 1
• 230000002265 prevention Effects 0.000 description 1
• 150000003141 primary amines Chemical class 0.000 description 1
• 230000008569 process Effects 0.000 description 1
• 102000004196 processed proteins & peptides Human genes 0.000 description 1
• 230000002035 prolonged effect Effects 0.000 description 1
• SXYFKXOFMCIXQW-UHFFFAOYSA-N propanedioyl dichloride Chemical compound ClC(=O)CC(Cl)=O SXYFKXOFMCIXQW-UHFFFAOYSA-N 0.000 description 1
• 150000004672 propanoic acids Chemical class 0.000 description 1
• 239000003380 propellant Substances 0.000 description 1
• WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
• 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
• 239000011241 protective layer Substances 0.000 description 1
• 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
• 125000003373 pyrazinyl group Chemical group 0.000 description 1
• 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
• 125000003226 pyrazolyl group Chemical group 0.000 description 1
• 125000002098 pyridazinyl group Chemical group 0.000 description 1
• 125000004076 pyridyl group Chemical group 0.000 description 1
• 125000005400 pyridylcarbonyl group Chemical group N1=C(C=CC=C1)C(=O)* 0.000 description 1
• 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
• 125000000168 pyrrolyl group Chemical group 0.000 description 1
• 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
• 125000001453 quaternary ammonium group Chemical group 0.000 description 1
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
• 238000001953 recrystallisation Methods 0.000 description 1
• 210000000664 rectum Anatomy 0.000 description 1
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 150000003335 secondary amines Chemical class 0.000 description 1
• 238000000926 separation method Methods 0.000 description 1
• 239000008159 sesame oil Substances 0.000 description 1
• 235000011803 sesame oil Nutrition 0.000 description 1
• 150000004760 silicates Chemical class 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
• 150000003385 sodium Chemical class 0.000 description 1
• URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
• 239000012279 sodium borohydride Substances 0.000 description 1
• 229910000033 sodium borohydride Inorganic materials 0.000 description 1
• 229910000029 sodium carbonate Inorganic materials 0.000 description 1
• 239000001509 sodium citrate Substances 0.000 description 1
• NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
• AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
• 235000019345 sodium thiosulphate Nutrition 0.000 description 1
• 239000007909 solid dosage form Substances 0.000 description 1
• 239000008247 solid mixture Substances 0.000 description 1
• 239000004334 sorbic acid Substances 0.000 description 1
• 235000010199 sorbic acid Nutrition 0.000 description 1
• 229940075582 sorbic acid Drugs 0.000 description 1
• 239000000600 sorbitol Substances 0.000 description 1
• 239000007921 spray Substances 0.000 description 1
• 230000007480 spreading Effects 0.000 description 1
• 239000003381 stabilizer Substances 0.000 description 1
• 210000000130 stem cell Anatomy 0.000 description 1
• 239000008223 sterile water Substances 0.000 description 1
• 239000003206 sterilizing agent Substances 0.000 description 1
• 238000010254 subcutaneous injection Methods 0.000 description 1
• 239000007929 subcutaneous injection Substances 0.000 description 1
• 238000006467 substitution reaction Methods 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
• 235000011044 succinic acid Nutrition 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid group Chemical group C(CCC(=O)O)(=O)O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
• 150000003457 sulfones Chemical class 0.000 description 1
• 150000003462 sulfoxides Chemical class 0.000 description 1
• 239000011593 sulfur Substances 0.000 description 1
• YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
• 238000010189 synthetic method Methods 0.000 description 1
• 239000006188 syrup Substances 0.000 description 1
• 235000020357 syrup Nutrition 0.000 description 1
• 239000000454 talc Substances 0.000 description 1
• 229910052623 talc Inorganic materials 0.000 description 1
• 235000012222 talc Nutrition 0.000 description 1
• 229940095064 tartrate Drugs 0.000 description 1
• 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• FFPDSVNJARXKCJ-UHFFFAOYSA-N tert-butyl 3-(4-bromophenyl)prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=CC1=CC=C(Br)C=C1 FFPDSVNJARXKCJ-UHFFFAOYSA-N 0.000 description 1
• 150000003512 tertiary amines Chemical class 0.000 description 1
• JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
• CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
• BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
• QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
• 125000003831 tetrazolyl group Chemical group 0.000 description 1
• 229940124597 therapeutic agent Drugs 0.000 description 1
• 230000004797 therapeutic response Effects 0.000 description 1
• 125000000335 thiazolyl group Chemical group 0.000 description 1
• 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 description 1
• 125000004001 thioalkyl group Chemical group 0.000 description 1
• 150000003568 thioethers Chemical class 0.000 description 1
• FKKJJPMGAWGYPN-UHFFFAOYSA-N thiophen-2-ylmethanamine Chemical compound NCC1=CC=CS1 FKKJJPMGAWGYPN-UHFFFAOYSA-N 0.000 description 1
• ZPHGMBGIFODUMF-UHFFFAOYSA-N thiophen-2-ylmethanol Chemical compound OCC1=CC=CS1 ZPHGMBGIFODUMF-UHFFFAOYSA-N 0.000 description 1
• 230000000451 tissue damage Effects 0.000 description 1
• 231100000827 tissue damage Toxicity 0.000 description 1
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
• 125000003944 tolyl group Chemical group 0.000 description 1
• 230000000699 topical effect Effects 0.000 description 1
• 231100000419 toxicity Toxicity 0.000 description 1
• 230000001988 toxicity Effects 0.000 description 1
• 238000012546 transfer Methods 0.000 description 1
• QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
• ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
• GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
• 229960004799 tryptophan Drugs 0.000 description 1
• ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
• 150000003672 ureas Chemical class 0.000 description 1
• 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 229960004295 valine Drugs 0.000 description 1
• 210000003556 vascular endothelial cell Anatomy 0.000 description 1
• 235000015112 vegetable and seed oil Nutrition 0.000 description 1
• 239000008158 vegetable oil Substances 0.000 description 1
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
• 238000010792 warming Methods 0.000 description 1
• 229910052725 zinc Inorganic materials 0.000 description 1