ES2425051T3 - Tiazolil-dihidro-quinazolinas - Google Patents
Tiazolil-dihidro-quinazolinas Download PDFInfo
- Publication number
- ES2425051T3 ES2425051T3 ES07727385T ES07727385T ES2425051T3 ES 2425051 T3 ES2425051 T3 ES 2425051T3 ES 07727385 T ES07727385 T ES 07727385T ES 07727385 T ES07727385 T ES 07727385T ES 2425051 T3 ES2425051 T3 ES 2425051T3
- Authority
- ES
- Spain
- Prior art keywords
- group
- alkyl
- hydrogen
- amino
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 99
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 62
- 239000001257 hydrogen Substances 0.000 claims abstract description 61
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 37
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 35
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 31
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 29
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 27
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 23
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 21
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 21
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 13
- 101100495923 Schizosaccharomyces pombe (strain 972 / ATCC 24843) chr2 gene Proteins 0.000 claims abstract description 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 7
- 239000000460 chlorine Substances 0.000 claims description 192
- 238000000034 method Methods 0.000 claims description 192
- -1 EGFR inhibitors Substances 0.000 claims description 154
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 80
- 150000003839 salts Chemical class 0.000 claims description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims description 32
- 239000002253 acid Substances 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 31
- 125000005842 heteroatom Chemical group 0.000 claims description 29
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 24
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
- 201000010099 disease Diseases 0.000 claims description 22
- 239000003814 drug Substances 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 230000002757 inflammatory effect Effects 0.000 claims description 19
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 239000001301 oxygen Substances 0.000 claims description 17
- 230000000172 allergic effect Effects 0.000 claims description 16
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 16
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 15
- 150000007513 acids Chemical class 0.000 claims description 15
- 206010006451 bronchitis Diseases 0.000 claims description 15
- 239000004480 active ingredient Substances 0.000 claims description 14
- 208000027866 inflammatory disease Diseases 0.000 claims description 14
- 125000003003 spiro group Chemical group 0.000 claims description 14
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 13
- 208000010668 atopic eczema Diseases 0.000 claims description 13
- 239000005557 antagonist Substances 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
- 230000003454 betamimetic effect Effects 0.000 claims description 12
- 239000012453 solvate Substances 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 11
- 239000000808 adrenergic beta-agonist Substances 0.000 claims description 11
- 208000026935 allergic disease Diseases 0.000 claims description 11
- 150000004677 hydrates Chemical class 0.000 claims description 11
- 125000004450 alkenylene group Chemical group 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- YEESKJGWJFYOOK-IJHYULJSSA-N leukotriene D4 Chemical compound CCCCC\C=C/C\C=C/C=C/C=C/[C@H]([C@@H](O)CCCC(O)=O)SC[C@H](N)C(=O)NCC(O)=O YEESKJGWJFYOOK-IJHYULJSSA-N 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000004419 alkynylene group Chemical group 0.000 claims description 8
- 229940121647 egfr inhibitor Drugs 0.000 claims description 8
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims description 7
- 206010001889 Alveolitis Diseases 0.000 claims description 6
- 201000003883 Cystic fibrosis Diseases 0.000 claims description 6
- 208000000592 Nasal Polyps Diseases 0.000 claims description 6
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 6
- 201000010105 allergic rhinitis Diseases 0.000 claims description 6
- 239000003246 corticosteroid Substances 0.000 claims description 6
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 6
- 201000001155 extrinsic allergic alveolitis Diseases 0.000 claims description 6
- 208000022098 hypersensitivity pneumonitis Diseases 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 5
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 5
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 206010025135 lupus erythematosus Diseases 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- 231100000331 toxic Toxicity 0.000 claims description 5
- 230000002588 toxic effect Effects 0.000 claims description 5
- 206010037423 Pulmonary oedema Diseases 0.000 claims description 4
- 208000006673 asthma Diseases 0.000 claims description 4
- 230000001580 bacterial effect Effects 0.000 claims description 4
- 230000001684 chronic effect Effects 0.000 claims description 4
- 229960001334 corticosteroids Drugs 0.000 claims description 4
- 125000005724 cycloalkenylene group Chemical group 0.000 claims description 4
- 206010049153 Allergic sinusitis Diseases 0.000 claims description 3
- 208000035143 Bacterial infection Diseases 0.000 claims description 3
- 206010006458 Bronchitis chronic Diseases 0.000 claims description 3
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 3
- 206010009137 Chronic sinusitis Diseases 0.000 claims description 3
- 208000027932 Collagen disease Diseases 0.000 claims description 3
- 206010011224 Cough Diseases 0.000 claims description 3
- 206010014561 Emphysema Diseases 0.000 claims description 3
- 241000233866 Fungi Species 0.000 claims description 3
- 206010035664 Pneumonia Diseases 0.000 claims description 3
- 206010035742 Pneumonitis Diseases 0.000 claims description 3
- 201000009594 Systemic Scleroderma Diseases 0.000 claims description 3
- 206010042953 Systemic sclerosis Diseases 0.000 claims description 3
- 208000036142 Viral infection Diseases 0.000 claims description 3
- 208000006682 alpha 1-Antitrypsin Deficiency Diseases 0.000 claims description 3
- 229940065524 anticholinergics inhalants for obstructive airway diseases Drugs 0.000 claims description 3
- 229940125715 antihistaminic agent Drugs 0.000 claims description 3
- 239000000739 antihistaminic agent Substances 0.000 claims description 3
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 3
- 201000009267 bronchiectasis Diseases 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 208000029771 childhood onset asthma Diseases 0.000 claims description 3
- 239000000812 cholinergic antagonist Substances 0.000 claims description 3
- 208000007451 chronic bronchitis Diseases 0.000 claims description 3
- 208000027157 chronic rhinosinusitis Diseases 0.000 claims description 3
- 244000000013 helminth Species 0.000 claims description 3
- 208000015181 infectious disease Diseases 0.000 claims description 3
- 230000002458 infectious effect Effects 0.000 claims description 3
- 208000037916 non-allergic rhinitis Diseases 0.000 claims description 3
- 239000002935 phosphatidylinositol 3 kinase inhibitor Substances 0.000 claims description 3
- 208000005333 pulmonary edema Diseases 0.000 claims description 3
- 201000000306 sarcoidosis Diseases 0.000 claims description 3
- 230000009385 viral infection Effects 0.000 claims description 3
- 206010052613 Allergic bronchitis Diseases 0.000 claims description 2
- 229940052760 dopamine agonists Drugs 0.000 claims description 2
- 239000003136 dopamine receptor stimulating agent Substances 0.000 claims description 2
- 125000004367 cycloalkylaryl group Chemical group 0.000 claims 1
- 239000000890 drug combination Substances 0.000 claims 1
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims 1
- 230000002685 pulmonary effect Effects 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 69
- 150000003254 radicals Chemical class 0.000 description 67
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 49
- 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 38
- 238000004458 analytical method Methods 0.000 description 36
- 239000000243 solution Substances 0.000 description 29
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- 239000011541 reaction mixture Substances 0.000 description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 150000002148 esters Chemical class 0.000 description 21
- 239000012074 organic phase Substances 0.000 description 21
- 125000001424 substituent group Chemical group 0.000 description 20
- 239000007787 solid Substances 0.000 description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 15
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- 239000013543 active substance Substances 0.000 description 14
- 239000000543 intermediate Substances 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 12
- 239000000725 suspension Substances 0.000 description 12
- 229920002261 Corn starch Polymers 0.000 description 11
- 239000008120 corn starch Substances 0.000 description 11
- 229940099112 cornstarch Drugs 0.000 description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 11
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 11
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 11
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 10
- 239000008298 dragée Substances 0.000 description 10
- 239000011737 fluorine Substances 0.000 description 10
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 10
- QWBWILPXRQIFOE-UHFFFAOYSA-N n-[8-[2-chloro-5-[3-(methylamino)prop-1-ynyl]phenyl]-4,5-dihydro-[1,3]thiazolo[4,5-h]quinazolin-2-yl]acetamide Chemical compound CNCC#CC1=CC=C(Cl)C(C=2N=C3C=4SC(NC(C)=O)=NC=4CCC3=CN=2)=C1 QWBWILPXRQIFOE-UHFFFAOYSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 9
- 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 description 9
- 235000019359 magnesium stearate Nutrition 0.000 description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
- 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 8
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 8
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 8
- 239000008101 lactose Substances 0.000 description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 125000000392 cycloalkenyl group Chemical group 0.000 description 7
- FXORZKOZOQWVMQ-UHFFFAOYSA-L dichloropalladium;triphenylphosphane Chemical compound Cl[Pd]Cl.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 FXORZKOZOQWVMQ-UHFFFAOYSA-L 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 206010010741 Conjunctivitis Diseases 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
- 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 6
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 6
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 6
- 125000004260 quinazolin-2-yl group Chemical group [H]C1=NC(*)=NC2=C1C([H])=C([H])C([H])=C2[H] 0.000 description 6
- 208000017520 skin disease Diseases 0.000 description 6
- 230000001225 therapeutic effect Effects 0.000 description 6
- 239000003643 water by type Substances 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
- 206010061218 Inflammation Diseases 0.000 description 5
- 102000038030 PI3Ks Human genes 0.000 description 5
- 108091007960 PI3Ks Proteins 0.000 description 5
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 239000012300 argon atmosphere Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 150000003842 bromide salts Chemical class 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 230000004054 inflammatory process Effects 0.000 description 5
- 239000011630 iodine Substances 0.000 description 5
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 235000011181 potassium carbonates Nutrition 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- 239000000829 suppository Substances 0.000 description 5
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 4
- PZJFUNZDCRKXPZ-UHFFFAOYSA-N 2,5-dihydro-1h-tetrazole Chemical compound C1NNN=N1 PZJFUNZDCRKXPZ-UHFFFAOYSA-N 0.000 description 4
- DHSYPDYDWRRALD-UHFFFAOYSA-N 2-(cyclopropylmethoxy)quinazoline Chemical compound N=1C=C2C=CC=CC2=NC=1OCC1CC1 DHSYPDYDWRRALD-UHFFFAOYSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 4
- 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 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 230000001363 autoimmune Effects 0.000 description 4
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 229940102396 methyl bromide Drugs 0.000 description 4
- GZUXJHMPEANEGY-UHFFFAOYSA-N methyl bromide Substances BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 210000002850 nasal mucosa Anatomy 0.000 description 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 4
- 235000021317 phosphate Nutrition 0.000 description 4
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000004007 reversed phase HPLC Methods 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 3
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 3
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 208000011231 Crohn disease Diseases 0.000 description 3
- 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 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- 238000003820 Medium-pressure liquid chromatography Methods 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 208000017169 kidney disease Diseases 0.000 description 3
- 230000000670 limiting effect Effects 0.000 description 3
- HCLWEABQPYEHTL-UHFFFAOYSA-N n-[8-(2-chloro-5-iodophenyl)-4,5-dihydro-[1,3]thiazolo[4,5-h]quinazolin-2-yl]acetamide Chemical compound N1=C2C=3SC(NC(=O)C)=NC=3CCC2=CN=C1C1=CC(I)=CC=C1Cl HCLWEABQPYEHTL-UHFFFAOYSA-N 0.000 description 3
- 125000005981 pentynyl group Chemical group 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 230000002062 proliferating effect Effects 0.000 description 3
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 3
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 235000000346 sugar Nutrition 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 2
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 description 2
- GDKOYYDQISQOMH-UHFFFAOYSA-N 1-ethynylcyclohexan-1-amine Chemical compound C#CC1(N)CCCCC1 GDKOYYDQISQOMH-UHFFFAOYSA-N 0.000 description 2
- 125000004806 1-methylethylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 2
- ODMMNALOCMNQJZ-UHFFFAOYSA-N 1H-pyrrolizine Chemical compound C1=CC=C2CC=CN21 ODMMNALOCMNQJZ-UHFFFAOYSA-N 0.000 description 2
- QMNUDYFKZYBWQX-UHFFFAOYSA-N 1H-quinazolin-4-one Chemical compound C1=CC=C2C(=O)N=CNC2=C1 QMNUDYFKZYBWQX-UHFFFAOYSA-N 0.000 description 2
- VKSLAFQKMBGIEN-UHFFFAOYSA-N 2-chloro-5-iodobenzenecarboximidamide Chemical compound NC(=N)C1=CC(I)=CC=C1Cl VKSLAFQKMBGIEN-UHFFFAOYSA-N 0.000 description 2
- TUYKECFWOROKNW-UHFFFAOYSA-N 2-fluoro-5-iodobenzenecarboximidamide Chemical compound NC(=N)C1=CC(I)=CC=C1F TUYKECFWOROKNW-UHFFFAOYSA-N 0.000 description 2
- BWYJJZBRYSADRP-UHFFFAOYSA-N 2-methoxyquinazoline Chemical compound C1=CC=CC2=NC(OC)=NC=C21 BWYJJZBRYSADRP-UHFFFAOYSA-N 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
- ZMPRRFPMMJQXPP-UHFFFAOYSA-N 2-sulfobenzoic acid Chemical class OC(=O)C1=CC=CC=C1S(O)(=O)=O ZMPRRFPMMJQXPP-UHFFFAOYSA-N 0.000 description 2
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 2
- ULMFXAMQUGLVGA-LJQANCHMSA-N 3-[[2-methoxy-4-[(2-methylphenyl)sulfonylcarbamoyl]phenyl]methyl]-1-methyl-n-[(2r)-4,4,4-trifluoro-2-methylbutyl]indole-5-carboxamide Chemical compound C=1C=C(CC=2C3=CC(=CC=C3N(C)C=2)C(=O)NC[C@H](C)CC(F)(F)F)C(OC)=CC=1C(=O)NS(=O)(=O)C1=CC=CC=C1C ULMFXAMQUGLVGA-LJQANCHMSA-N 0.000 description 2
- LFIXHYHYZYTFHT-UHFFFAOYSA-N 3-chloro-5-iodobenzenecarboximidamide Chemical compound NC(=N)C1=CC(Cl)=CC(I)=C1 LFIXHYHYZYTFHT-UHFFFAOYSA-N 0.000 description 2
- XJQGSJBTLSVOQF-UHFFFAOYSA-N 3-iodobenzenecarboximidamide Chemical compound NC(=N)C1=CC=CC(I)=C1 XJQGSJBTLSVOQF-UHFFFAOYSA-N 0.000 description 2
- CVDXFPBVOIERBH-JWQCQUIFSA-N 4-[(4ar,10bs)-9-ethoxy-8-methoxy-2-methyl-3,4,4a,10b-tetrahydro-1h-benzo[c][1,6]naphthyridin-6-yl]-n,n-di(propan-2-yl)benzamide Chemical compound N([C@@H]1CCN(C)C[C@@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CC=C(C(=O)N(C(C)C)C(C)C)C=C1 CVDXFPBVOIERBH-JWQCQUIFSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical class OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- PYUGFOWNYMLROI-KPKJPENVSA-N 8-[(e)-2-[4-[4-(4-fluorophenyl)butoxy]phenyl]ethenyl]-2-(2h-tetrazol-5-yl)chromen-4-one Chemical compound C1=CC(F)=CC=C1CCCCOC(C=C1)=CC=C1\C=C\C1=CC=CC2=C1OC(C=1NN=NN=1)=CC2=O PYUGFOWNYMLROI-KPKJPENVSA-N 0.000 description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
- 208000002874 Acne Vulgaris Diseases 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
- 206010002556 Ankylosing Spondylitis Diseases 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical compound C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-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
- 208000006029 Cardiomegaly Diseases 0.000 description 2
- 206010008909 Chronic Hepatitis Diseases 0.000 description 2
- 206010009900 Colitis ulcerative Diseases 0.000 description 2
- 206010010744 Conjunctivitis allergic Diseases 0.000 description 2
- 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 2
- 206010012438 Dermatitis atopic Diseases 0.000 description 2
- 206010012442 Dermatitis contact Diseases 0.000 description 2
- 206010012468 Dermatitis herpetiformis Diseases 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 206010015150 Erythema Diseases 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 230000005526 G1 to G0 transition Effects 0.000 description 2
- 206010018364 Glomerulonephritis Diseases 0.000 description 2
- DHCLVCXQIBBOPH-UHFFFAOYSA-N Glycerol 2-phosphate Chemical compound OCC(CO)OP(O)(O)=O DHCLVCXQIBBOPH-UHFFFAOYSA-N 0.000 description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
- GNWHRHGTIBRNSM-UHFFFAOYSA-N IC-87114 Chemical compound CC1=CC=CC=C1N1C(=O)C2=C(C)C=CC=C2N=C1CN1C2=NC=NC(N)=C2N=C1 GNWHRHGTIBRNSM-UHFFFAOYSA-N 0.000 description 2
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 102000001253 Protein Kinase Human genes 0.000 description 2
- 201000004681 Psoriasis Diseases 0.000 description 2
- 201000001263 Psoriatic Arthritis Diseases 0.000 description 2
- 208000036824 Psoriatic arthropathy Diseases 0.000 description 2
- 208000006311 Pyoderma Diseases 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 206010039710 Scleroderma Diseases 0.000 description 2
- 206010040070 Septic Shock Diseases 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 206010042033 Stevens-Johnson syndrome Diseases 0.000 description 2
- 231100000168 Stevens-Johnson syndrome Toxicity 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 239000012317 TBTU Substances 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- DHCOPPHTVOXDKU-UHFFFAOYSA-N Tofimilast Chemical compound C1CN2C(C=3SC=CC=3)=NN=C2C2=C1C(CC)=NN2C1CCCC1 DHCOPPHTVOXDKU-UHFFFAOYSA-N 0.000 description 2
- 201000006704 Ulcerative Colitis Diseases 0.000 description 2
- 208000024780 Urticaria Diseases 0.000 description 2
- 206010046851 Uveitis Diseases 0.000 description 2
- 206010047642 Vitiligo Diseases 0.000 description 2
- CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 description 2
- 206010000496 acne Diseases 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 208000002205 allergic conjunctivitis Diseases 0.000 description 2
- 208000004631 alopecia areata Diseases 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 208000024998 atopic conjunctivitis Diseases 0.000 description 2
- 201000008937 atopic dermatitis Diseases 0.000 description 2
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 210000000481 breast Anatomy 0.000 description 2
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 2
- 125000005622 butynylene group Chemical group 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- CFBUZOUXXHZCFB-OYOVHJISSA-N chembl511115 Chemical compound COC1=CC=C([C@@]2(CC[C@H](CC2)C(O)=O)C#N)C=C1OC1CCCC1 CFBUZOUXXHZCFB-OYOVHJISSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 208000010247 contact dermatitis Diseases 0.000 description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 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
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 2
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 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
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 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 2
- 238000000151 deposition Methods 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 231100000321 erythema Toxicity 0.000 description 2
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 2
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 2
- 208000030533 eye disease Diseases 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000003325 follicular Effects 0.000 description 2
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 208000006454 hepatitis Diseases 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
- 208000016036 idiopathic nephrotic syndrome Diseases 0.000 description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 201000006334 interstitial nephritis Diseases 0.000 description 2
- 230000000622 irritating effect Effects 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical class OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 206010023332 keratitis Diseases 0.000 description 2
- 125000000468 ketone group Chemical group 0.000 description 2
- 229940043355 kinase inhibitor Drugs 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 210000004072 lung Anatomy 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 2
- 229940016286 microcrystalline cellulose Drugs 0.000 description 2
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 2
- 239000008108 microcrystalline cellulose Substances 0.000 description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 2
- 201000006417 multiple sclerosis Diseases 0.000 description 2
- DPHDSIQHVGSITN-UHFFFAOYSA-N n-(3,5-dichloropyridin-4-yl)-2-[1-[(4-fluorophenyl)methyl]-5-hydroxyindol-3-yl]-2-oxoacetamide Chemical compound C1=C(C(=O)C(=O)NC=2C(=CN=CC=2Cl)Cl)C2=CC(O)=CC=C2N1CC1=CC=C(F)C=C1 DPHDSIQHVGSITN-UHFFFAOYSA-N 0.000 description 2
- OBAORJLSQFZLGO-UHFFFAOYSA-N n-(6-formyl-7-oxo-5,6-dihydro-4h-1,3-benzothiazol-2-yl)acetamide Chemical compound C1CC(C=O)C(=O)C2=C1N=C(NC(=O)C)S2 OBAORJLSQFZLGO-UHFFFAOYSA-N 0.000 description 2
- NQOYGOQOTVPTCJ-UHFFFAOYSA-N n-[8-[2-chloro-5-(2-piperidin-4-ylethynyl)phenyl]-4,5-dihydro-[1,3]thiazolo[4,5-h]quinazolin-2-yl]acetamide Chemical compound N1=C2C=3SC(NC(=O)C)=NC=3CCC2=CN=C1C(C(=CC=1)Cl)=CC=1C#CC1CCNCC1 NQOYGOQOTVPTCJ-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 125000006574 non-aromatic ring group Chemical group 0.000 description 2
- 125000001400 nonyl 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])[H] 0.000 description 2
- 125000002347 octyl 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])[H] 0.000 description 2
- 201000008482 osteoarthritis Diseases 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 150000002942 palmitic acid derivatives Chemical class 0.000 description 2
- 230000007170 pathology Effects 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- 239000003757 phosphotransferase inhibitor Substances 0.000 description 2
- 125000005547 pivalate group Chemical group 0.000 description 2
- 159000000001 potassium salts Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 108060006633 protein kinase Proteins 0.000 description 2
- BWESROVQGZSBRX-UHFFFAOYSA-N pyrido[3,2-d]pyrimidine Chemical compound C1=NC=NC2=CC=CN=C21 BWESROVQGZSBRX-UHFFFAOYSA-N 0.000 description 2
- 201000004700 rosacea Diseases 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 2
- 239000004334 sorbic acid Substances 0.000 description 2
- 235000010199 sorbic acid Nutrition 0.000 description 2
- 229940075582 sorbic acid Drugs 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 229940032147 starch Drugs 0.000 description 2
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
- XWTYSIMOBUGWOL-UHFFFAOYSA-N (+-)-Terbutaline Chemical compound CC(C)(C)NCC(O)C1=CC(O)=CC(O)=C1 XWTYSIMOBUGWOL-UHFFFAOYSA-N 0.000 description 1
- CVKZDWKGOQOJMZ-UHFFFAOYSA-N (1-diazo-2-oxopropyl) dihydrogen phosphate Chemical compound CC(=O)C(=[N+]=[N-])OP(O)(O)=O CVKZDWKGOQOJMZ-UHFFFAOYSA-N 0.000 description 1
- SODJJQTYBSNLPQ-ZCFIWIBFSA-N (2s)-2-ethynylpyrrolidine Chemical compound C#C[C@@H]1CCCN1 SODJJQTYBSNLPQ-ZCFIWIBFSA-N 0.000 description 1
- 125000006590 (C2-C6) alkenylene group Chemical group 0.000 description 1
- 125000006591 (C2-C6) alkynylene group Chemical group 0.000 description 1
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 description 1
- SEPPVOUBHWNCAW-FNORWQNLSA-N (E)-4-oxonon-2-enal Chemical compound CCCCCC(=O)\C=C\C=O SEPPVOUBHWNCAW-FNORWQNLSA-N 0.000 description 1
- NDAUXUAQIAJITI-LBPRGKRZSA-N (R)-salbutamol Chemical compound CC(C)(C)NC[C@H](O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-LBPRGKRZSA-N 0.000 description 1
- ZGYIXVSQHOKQRZ-COIATFDQSA-N (e)-n-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-3-cyano-7-[(3s)-oxolan-3-yl]oxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound N#CC1=CN=C2C=C(O[C@@H]3COCC3)C(NC(=O)/C=C/CN(C)C)=CC2=C1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 ZGYIXVSQHOKQRZ-COIATFDQSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- TZCPCKNHXULUIY-RGULYWFUSA-N 1,2-distearoyl-sn-glycero-3-phosphoserine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCCCCCCCCCCC TZCPCKNHXULUIY-RGULYWFUSA-N 0.000 description 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- IMLSAISZLJGWPP-UHFFFAOYSA-N 1,3-dithiolane Chemical compound C1CSCS1 IMLSAISZLJGWPP-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- CMLDRMOPXHHMKT-UHFFFAOYSA-N 1,4-dioxa-10-azaspiro[4.5]decane Chemical compound O1CCOC11NCCCC1 CMLDRMOPXHHMKT-UHFFFAOYSA-N 0.000 description 1
- FWJDRRZEOQPJSP-UHFFFAOYSA-N 1-but-3-ynyl-1,3-dimethylurea Chemical compound CNC(=O)N(C)CCC#C FWJDRRZEOQPJSP-UHFFFAOYSA-N 0.000 description 1
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
- IUWIMBGMEPCKJA-UHFFFAOYSA-N 1-cyclopentyl-4-ethynyl-4-methoxypiperidine Chemical compound C1CC(OC)(C#C)CCN1C1CCCC1 IUWIMBGMEPCKJA-UHFFFAOYSA-N 0.000 description 1
- CUZCJXOXLNDDBB-UHFFFAOYSA-N 1-ethynyl-n,n-dimethylcyclopentan-1-amine Chemical compound CN(C)C1(C#C)CCCC1 CUZCJXOXLNDDBB-UHFFFAOYSA-N 0.000 description 1
- QYLFHLNFIHBCPR-UHFFFAOYSA-N 1-ethynylcyclohexan-1-ol Chemical compound C#CC1(O)CCCCC1 QYLFHLNFIHBCPR-UHFFFAOYSA-N 0.000 description 1
- UGOQKSGJGCADAG-UHFFFAOYSA-N 1-prop-2-ynylimidazole Chemical compound C#CCN1C=CN=C1 UGOQKSGJGCADAG-UHFFFAOYSA-N 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- POXWDTQUDZUOGP-UHFFFAOYSA-N 1h-1,4-diazepine Chemical compound N1C=CC=NC=C1 POXWDTQUDZUOGP-UHFFFAOYSA-N 0.000 description 1
- LITNEAPWQHVPOK-FFSVYQOJSA-N 2(1h)-pyrimidinone, 5-[3-[(1s,2s,4r)-bicyclo[2.2.1]hept-2-yloxy]-4-methoxyphenyl]tetrahydro- Chemical compound C1=C(O[C@@H]2[C@H]3CC[C@H](C3)C2)C(OC)=CC=C1C1CNC(=O)NC1 LITNEAPWQHVPOK-FFSVYQOJSA-N 0.000 description 1
- OXBLVCZKDOZZOJ-UHFFFAOYSA-N 2,3-Dihydrothiophene Chemical compound C1CC=CS1 OXBLVCZKDOZZOJ-UHFFFAOYSA-N 0.000 description 1
- XXXBRMHCEXRQRE-UHFFFAOYSA-N 2-[(2,6-diaminopurin-9-yl)methyl]-5-methyl-3-(2-methylphenyl)quinazolin-4-one Chemical compound CC1=CC=CC=C1N1C(=O)C2=C(C)C=CC=C2N=C1CN1C2=NC(N)=NC(N)=C2N=C1 XXXBRMHCEXRQRE-UHFFFAOYSA-N 0.000 description 1
- ORFWNKQOWFUESB-UHFFFAOYSA-N 2-[(2,6-diaminopyrimidin-4-yl)sulfanylmethyl]-5-methyl-3-(2-methylphenyl)quinazolin-4-one Chemical compound CC1=CC=CC=C1N1C(=O)C2=C(C)C=CC=C2N=C1CSC1=CC(N)=NC(N)=N1 ORFWNKQOWFUESB-UHFFFAOYSA-N 0.000 description 1
- PGKGDAOZGPWYBX-UHFFFAOYSA-N 2-[(2-amino-6-chloropurin-9-yl)methyl]-5-methyl-3-(2-methylphenyl)quinazolin-4-one Chemical compound CC1=CC=CC=C1N1C(=O)C2=C(C)C=CC=C2N=C1CN1C2=NC(N)=NC(Cl)=C2N=C1 PGKGDAOZGPWYBX-UHFFFAOYSA-N 0.000 description 1
- GLISRNOWJQFSKQ-UHFFFAOYSA-N 2-[(2-amino-7h-purin-6-yl)sulfanylmethyl]-3-(cyclopropylmethyl)-5-methylquinazolin-4-one Chemical compound O=C1C=2C(C)=CC=CC=2N=C(CSC=2C=3N=CNC=3N=C(N)N=2)N1CC1CC1 GLISRNOWJQFSKQ-UHFFFAOYSA-N 0.000 description 1
- DAHXTJXOAVOOMS-UHFFFAOYSA-N 2-[(2-amino-7h-purin-6-yl)sulfanylmethyl]-3-cyclohexyl-5-methylquinazolin-4-one Chemical compound O=C1C=2C(C)=CC=CC=2N=C(CSC=2C=3N=CNC=3N=C(N)N=2)N1C1CCCCC1 DAHXTJXOAVOOMS-UHFFFAOYSA-N 0.000 description 1
- WHWWGZDJBLYHFI-UHFFFAOYSA-N 2-[(2-amino-7h-purin-6-yl)sulfanylmethyl]-3-cyclopropyl-5-methylquinazolin-4-one Chemical compound O=C1C=2C(C)=CC=CC=2N=C(CSC=2C=3N=CNC=3N=C(N)N=2)N1C1CC1 WHWWGZDJBLYHFI-UHFFFAOYSA-N 0.000 description 1
- DPJDASRPEANFHE-UHFFFAOYSA-N 2-[(2-amino-7h-purin-6-yl)sulfanylmethyl]-5-methyl-3-(2-methylphenyl)quinazolin-4-one Chemical compound CC1=CC=CC=C1N1C(=O)C2=C(C)C=CC=C2N=C1CSC1=NC(N)=NC2=C1N=CN2 DPJDASRPEANFHE-UHFFFAOYSA-N 0.000 description 1
- QZDNLQXEJWWDOY-UHFFFAOYSA-N 2-[(2-amino-7h-purin-6-yl)sulfanylmethyl]-5-methyl-3-(2-phenylethyl)quinazolin-4-one Chemical compound O=C1C=2C(C)=CC=CC=2N=C(CSC=2C=3N=CNC=3N=C(N)N=2)N1CCC1=CC=CC=C1 QZDNLQXEJWWDOY-UHFFFAOYSA-N 0.000 description 1
- LLFHXZQLQOWBSR-UHFFFAOYSA-N 2-[(3-amino-5-methylsulfanyl-1,2,4-triazol-1-yl)methyl]-5-methyl-3-(2-methylphenyl)quinazolin-4-one Chemical compound CSC1=NC(N)=NN1CC1=NC2=CC=CC(C)=C2C(=O)N1C1=CC=CC=C1C LLFHXZQLQOWBSR-UHFFFAOYSA-N 0.000 description 1
- DMVBXYZZXCWFNH-UHFFFAOYSA-N 2-[(4-amino-1,3,5-triazin-2-yl)sulfanylmethyl]-5-methyl-3-(2-methylphenyl)quinazolin-4-one Chemical compound CC1=CC=CC=C1N1C(=O)C2=C(C)C=CC=C2N=C1CSC1=NC=NC(N)=N1 DMVBXYZZXCWFNH-UHFFFAOYSA-N 0.000 description 1
- MCNANYUITPJRDV-UHFFFAOYSA-N 2-[(5-amino-3-methylsulfanyl-1,2,4-triazol-1-yl)methyl]-5-methyl-3-(2-methylphenyl)quinazolin-4-one Chemical compound N1=C(SC)N=C(N)N1CC1=NC2=CC=CC(C)=C2C(=O)N1C1=CC=CC=C1C MCNANYUITPJRDV-UHFFFAOYSA-N 0.000 description 1
- TYKASVTXCMXJQT-UHFFFAOYSA-N 2-[(6-amino-7h-purin-2-yl)sulfanylmethyl]-5-methyl-3-(2-methylphenyl)quinazolin-4-one Chemical compound CC1=CC=CC=C1N1C(=O)C2=C(C)C=CC=C2N=C1CSC1=NC(N)=C(N=CN2)C2=N1 TYKASVTXCMXJQT-UHFFFAOYSA-N 0.000 description 1
- IWGAQSJFPSNTKF-UHFFFAOYSA-N 2-[(6-aminopurin-7-yl)methyl]-5-methyl-3-(2-methylphenyl)quinazolin-4-one Chemical compound CC1=CC=CC=C1N1C(=O)C2=C(C)C=CC=C2N=C1CN1C2=C(N)N=CN=C2N=C1 IWGAQSJFPSNTKF-UHFFFAOYSA-N 0.000 description 1
- XIIBYVZCAGZAPQ-UHFFFAOYSA-N 2-[(6-aminopurin-9-yl)methyl]-3-(2-chlorophenyl)-5-fluoroquinazolin-4-one Chemical compound C1=NC=2C(N)=NC=NC=2N1CC1=NC2=CC=CC(F)=C2C(=O)N1C1=CC=CC=C1Cl XIIBYVZCAGZAPQ-UHFFFAOYSA-N 0.000 description 1
- VRZOWGGKIACNIC-UHFFFAOYSA-N 2-[(6-aminopurin-9-yl)methyl]-3-(2-chlorophenyl)-5-methylquinazolin-4-one Chemical compound O=C1C=2C(C)=CC=CC=2N=C(CN2C3=NC=NC(N)=C3N=C2)N1C1=CC=CC=C1Cl VRZOWGGKIACNIC-UHFFFAOYSA-N 0.000 description 1
- VVRQFRVUVPOQPU-UHFFFAOYSA-N 2-[(6-aminopurin-9-yl)methyl]-3-(2-chlorophenyl)-6,7-dimethoxyquinazolin-4-one Chemical compound O=C1C=2C=C(OC)C(OC)=CC=2N=C(CN2C3=NC=NC(N)=C3N=C2)N1C1=CC=CC=C1Cl VVRQFRVUVPOQPU-UHFFFAOYSA-N 0.000 description 1
- AMYMIDIYTQOWGQ-UHFFFAOYSA-N 2-[(6-aminopurin-9-yl)methyl]-3-(2-chloropyridin-3-yl)-5-methylquinazolin-4-one Chemical compound O=C1C=2C(C)=CC=CC=2N=C(CN2C3=NC=NC(N)=C3N=C2)N1C1=CC=CN=C1Cl AMYMIDIYTQOWGQ-UHFFFAOYSA-N 0.000 description 1
- SVCZPTVFVDMTSV-UHFFFAOYSA-N 2-[(6-aminopurin-9-yl)methyl]-3-(2-hydroxyphenyl)-5-methylquinazolin-4-one Chemical compound O=C1C=2C(C)=CC=CC=2N=C(CN2C3=NC=NC(N)=C3N=C2)N1C1=CC=CC=C1O SVCZPTVFVDMTSV-UHFFFAOYSA-N 0.000 description 1
- HHLQETOGUXOANM-UHFFFAOYSA-N 2-[(6-aminopurin-9-yl)methyl]-3-(cyclopropylmethyl)-5-methylquinazolin-4-one Chemical compound O=C1C=2C(C)=CC=CC=2N=C(CN2C3=NC=NC(N)=C3N=C2)N1CC1CC1 HHLQETOGUXOANM-UHFFFAOYSA-N 0.000 description 1
- MQJNDIUPTNHRFJ-UHFFFAOYSA-N 2-[(6-aminopurin-9-yl)methyl]-3-[2-[3-(dimethylamino)propoxy]phenyl]-5-methylquinazolin-4-one Chemical compound CN(C)CCCOC1=CC=CC=C1N1C(=O)C2=C(C)C=CC=C2N=C1CN1C2=NC=NC(N)=C2N=C1 MQJNDIUPTNHRFJ-UHFFFAOYSA-N 0.000 description 1
- VKQSKJCTWBCERY-UHFFFAOYSA-N 2-[(6-aminopurin-9-yl)methyl]-3-cyclohexyl-5-methylquinazolin-4-one Chemical compound O=C1C=2C(C)=CC=CC=2N=C(CN2C3=NC=NC(N)=C3N=C2)N1C1CCCCC1 VKQSKJCTWBCERY-UHFFFAOYSA-N 0.000 description 1
- JDFQBHREQMPUEC-UHFFFAOYSA-N 2-[(6-aminopurin-9-yl)methyl]-3-cyclopentyl-5-methylquinazolin-4-one Chemical compound O=C1C=2C(C)=CC=CC=2N=C(CN2C3=NC=NC(N)=C3N=C2)N1C1CCCC1 JDFQBHREQMPUEC-UHFFFAOYSA-N 0.000 description 1
- FPMFIIHYOJIALC-UHFFFAOYSA-N 2-[(6-aminopurin-9-yl)methyl]-3-cyclopropyl-5-methylquinazolin-4-one Chemical compound O=C1C=2C(C)=CC=CC=2N=C(CN2C3=NC=NC(N)=C3N=C2)N1C1CC1 FPMFIIHYOJIALC-UHFFFAOYSA-N 0.000 description 1
- MQGUQBFVGGNFBF-UHFFFAOYSA-N 2-[(6-aminopurin-9-yl)methyl]-5-chloro-3-(2-fluorophenyl)quinazolin-4-one Chemical compound C1=NC=2C(N)=NC=NC=2N1CC1=NC2=CC=CC(Cl)=C2C(=O)N1C1=CC=CC=C1F MQGUQBFVGGNFBF-UHFFFAOYSA-N 0.000 description 1
- IOOGLFCOTPZWOV-UHFFFAOYSA-N 2-[(6-aminopurin-9-yl)methyl]-5-chloro-3-(2-methoxyphenyl)quinazolin-4-one Chemical compound COC1=CC=CC=C1N1C(=O)C2=C(Cl)C=CC=C2N=C1CN1C2=NC=NC(N)=C2N=C1 IOOGLFCOTPZWOV-UHFFFAOYSA-N 0.000 description 1
- HKGGEZVQRAZEDJ-UHFFFAOYSA-N 2-[(6-aminopurin-9-yl)methyl]-5-chloro-3-(2-methylphenyl)quinazolin-4-one Chemical compound CC1=CC=CC=C1N1C(=O)C2=C(Cl)C=CC=C2N=C1CN1C2=NC=NC(N)=C2N=C1 HKGGEZVQRAZEDJ-UHFFFAOYSA-N 0.000 description 1
- LVMDQSBZDBGLET-UHFFFAOYSA-N 2-[(6-aminopurin-9-yl)methyl]-5-chloro-3-(2-phenylphenyl)quinazolin-4-one Chemical compound C1=NC=2C(N)=NC=NC=2N1CC1=NC2=CC=CC(Cl)=C2C(=O)N1C1=CC=CC=C1C1=CC=CC=C1 LVMDQSBZDBGLET-UHFFFAOYSA-N 0.000 description 1
- XCQOORVBLDOXOH-UHFFFAOYSA-N 2-[(6-aminopurin-9-yl)methyl]-5-methyl-3-(2-phenylmethoxyphenyl)quinazolin-4-one Chemical compound O=C1C=2C(C)=CC=CC=2N=C(CN2C3=NC=NC(N)=C3N=C2)N1C1=CC=CC=C1OCC1=CC=CC=C1 XCQOORVBLDOXOH-UHFFFAOYSA-N 0.000 description 1
- HZQXHJGJMGCUTP-UHFFFAOYSA-N 2-[(6-aminopurin-9-yl)methyl]-5-methyl-3-(2-prop-2-ynoxyphenyl)quinazolin-4-one Chemical compound O=C1C=2C(C)=CC=CC=2N=C(CN2C3=NC=NC(N)=C3N=C2)N1C1=CC=CC=C1OCC#C HZQXHJGJMGCUTP-UHFFFAOYSA-N 0.000 description 1
- XWHYLSLNUHYGHD-UHFFFAOYSA-N 2-[(6-aminopurin-9-yl)methyl]-5-methyl-3-(2-propan-2-ylphenyl)quinazolin-4-one Chemical compound CC(C)C1=CC=CC=C1N1C(=O)C2=C(C)C=CC=C2N=C1CN1C2=NC=NC(N)=C2N=C1 XWHYLSLNUHYGHD-UHFFFAOYSA-N 0.000 description 1
- OMTGAUBHYHQBIC-UHFFFAOYSA-N 2-[(6-aminopurin-9-yl)methyl]-5-methyl-3-[2-[2-(1-methylpyrrolidin-2-yl)ethoxy]phenyl]quinazolin-4-one Chemical compound CN1CCCC1CCOC1=CC=CC=C1N1C(=O)C2=C(C)C=CC=C2N=C1CN1C2=NC=NC(N)=C2N=C1 OMTGAUBHYHQBIC-UHFFFAOYSA-N 0.000 description 1
- CRAWDASOGPMBAA-UHFFFAOYSA-N 2-[(6-aminopurin-9-yl)methyl]-6-chloro-3-(2-chlorophenyl)quinazolin-4-one Chemical compound C1=NC=2C(N)=NC=NC=2N1CC1=NC2=CC=C(Cl)C=C2C(=O)N1C1=CC=CC=C1Cl CRAWDASOGPMBAA-UHFFFAOYSA-N 0.000 description 1
- PRNXFEYDFGYIMH-UHFFFAOYSA-N 2-[(6-aminopurin-9-yl)methyl]-8-chloro-3-(2-chlorophenyl)quinazolin-4-one Chemical compound C1=NC=2C(N)=NC=NC=2N1CC1=NC2=C(Cl)C=CC=C2C(=O)N1C1=CC=CC=C1Cl PRNXFEYDFGYIMH-UHFFFAOYSA-N 0.000 description 1
- KKVBQWUVUIRDLY-UHFFFAOYSA-N 2-[(7-aminotriazolo[4,5-d]pyrimidin-1-yl)methyl]-5-methyl-3-(2-methylphenyl)quinazolin-4-one Chemical compound CC1=CC=CC=C1N1C(=O)C2=C(C)C=CC=C2N=C1CN1C2=C(N)N=CN=C2N=N1 KKVBQWUVUIRDLY-UHFFFAOYSA-N 0.000 description 1
- UPOLRWJXUAMANE-UHFFFAOYSA-N 2-[(7-aminotriazolo[4,5-d]pyrimidin-3-yl)methyl]-5-methyl-3-(2-methylphenyl)quinazolin-4-one Chemical compound CC1=CC=CC=C1N1C(=O)C2=C(C)C=CC=C2N=C1CN1C2=NC=NC(N)=C2N=N1 UPOLRWJXUAMANE-UHFFFAOYSA-N 0.000 description 1
- CDMVWKJGRDDDLO-UHFFFAOYSA-N 2-[1-[(2-amino-7h-purin-6-yl)amino]ethyl]-5-chloro-3-(3-fluorophenyl)quinazolin-4-one Chemical compound N=1C(N)=NC=2NC=NC=2C=1NC(C)C1=NC2=CC=CC(Cl)=C2C(=O)N1C1=CC=CC(F)=C1 CDMVWKJGRDDDLO-UHFFFAOYSA-N 0.000 description 1
- PUYVJBBSBPUKBT-UHFFFAOYSA-N 2-[1-[(2-amino-7h-purin-6-yl)amino]ethyl]-5-methyl-3-(2-methylphenyl)quinazolin-4-one Chemical compound N=1C(N)=NC=2NC=NC=2C=1NC(C)C1=NC2=CC=CC(C)=C2C(=O)N1C1=CC=CC=C1C PUYVJBBSBPUKBT-UHFFFAOYSA-N 0.000 description 1
- XVWKIEIWIGAGIV-UHFFFAOYSA-N 2-[1-[(2-amino-7h-purin-6-yl)amino]propyl]-5-methyl-3-(2-methylphenyl)quinazolin-4-one Chemical compound N=1C(N)=NC=2NC=NC=2C=1NC(CC)C1=NC2=CC=CC(C)=C2C(=O)N1C1=CC=CC=C1C XVWKIEIWIGAGIV-UHFFFAOYSA-N 0.000 description 1
- PMIJDQUGMZYEHH-UHFFFAOYSA-N 2-[1-[(2-fluoro-7h-purin-6-yl)amino]ethyl]-5-methyl-3-(2-methylphenyl)quinazolin-4-one Chemical compound N=1C(F)=NC=2NC=NC=2C=1NC(C)C1=NC2=CC=CC(C)=C2C(=O)N1C1=CC=CC=C1C PMIJDQUGMZYEHH-UHFFFAOYSA-N 0.000 description 1
- PXHMYOPXPRUBJQ-UHFFFAOYSA-N 2-[1-[(2-fluoro-7h-purin-6-yl)amino]propyl]-5-methyl-3-(2-methylphenyl)quinazolin-4-one Chemical compound N=1C(F)=NC=2NC=NC=2C=1NC(CC)C1=NC2=CC=CC(C)=C2C(=O)N1C1=CC=CC=C1C PXHMYOPXPRUBJQ-UHFFFAOYSA-N 0.000 description 1
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
- RHCZAKKLWNRYLW-UHFFFAOYSA-N 2-[5-methyl-4-oxo-2-(7h-purin-6-ylsulfanylmethyl)quinazolin-3-yl]benzoic acid Chemical compound O=C1C=2C(C)=CC=CC=2N=C(CSC=2C=3N=CNC=3N=CN=2)N1C1=CC=CC=C1C(O)=O RHCZAKKLWNRYLW-UHFFFAOYSA-N 0.000 description 1
- NIJYZONQYZIWKO-UHFFFAOYSA-N 2-[[(2-amino-7h-purin-6-yl)amino]methyl]-3-(2-chlorophenyl)-5-fluoroquinazolin-4-one Chemical compound C=12N=CNC2=NC(N)=NC=1NCC1=NC2=CC=CC(F)=C2C(=O)N1C1=CC=CC=C1Cl NIJYZONQYZIWKO-UHFFFAOYSA-N 0.000 description 1
- NOYYMAUMYDJHSB-UHFFFAOYSA-N 2-[[(2-amino-7h-purin-6-yl)amino]methyl]-5-methyl-3-(2-methylphenyl)quinazolin-4-one Chemical compound CC1=CC=CC=C1N1C(=O)C2=C(C)C=CC=C2N=C1CNC1=NC(N)=NC2=C1N=CN2 NOYYMAUMYDJHSB-UHFFFAOYSA-N 0.000 description 1
- SCTILWQHMODCBQ-UHFFFAOYSA-N 2-[[(2-fluoro-7h-purin-6-yl)amino]methyl]-5-methyl-3-(2-methylphenyl)quinazolin-4-one Chemical compound CC1=CC=CC=C1N1C(=O)C2=C(C)C=CC=C2N=C1CNC1=NC(F)=NC2=C1N=CN2 SCTILWQHMODCBQ-UHFFFAOYSA-N 0.000 description 1
- QBNVCRIYUPVQIH-UHFFFAOYSA-N 2-[[2-amino-6-(ethylamino)pyrimidin-4-yl]sulfanylmethyl]-5-methyl-3-(2-methylphenyl)quinazolin-4-one Chemical compound NC1=NC(NCC)=CC(SCC=2N(C(=O)C3=C(C)C=CC=C3N=2)C=2C(=CC=CC=2)C)=N1 QBNVCRIYUPVQIH-UHFFFAOYSA-N 0.000 description 1
- QMMRTRAIDFEVAB-UHFFFAOYSA-N 2-[[6-(dimethylamino)purin-9-yl]methyl]-5-methyl-3-(2-methylphenyl)quinazolin-4-one Chemical compound C1=NC=2C(N(C)C)=NC=NC=2N1CC1=NC2=CC=CC(C)=C2C(=O)N1C1=CC=CC=C1C QMMRTRAIDFEVAB-UHFFFAOYSA-N 0.000 description 1
- MWFWIFXFNIZHHX-UHFFFAOYSA-N 2-[amino-(dimethylamino)-purin-9-ylmethyl]-5-methyl-3-(2-methylphenyl)quinazolin-4-one Chemical compound C1=NC2=CN=CN=C2N1C(N)(N(C)C)C1=NC2=CC=CC(C)=C2C(=O)N1C1=CC=CC=C1C MWFWIFXFNIZHHX-UHFFFAOYSA-N 0.000 description 1
- SPCKHVPPRJWQRZ-UHFFFAOYSA-N 2-benzhydryloxy-n,n-dimethylethanamine;2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 SPCKHVPPRJWQRZ-UHFFFAOYSA-N 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- RXNOBNYCCAEGJD-UHFFFAOYSA-N 2-chloro-5-iodobenzonitrile Chemical compound ClC1=CC=C(I)C=C1C#N RXNOBNYCCAEGJD-UHFFFAOYSA-N 0.000 description 1
- KVVDRQDTODKIJD-UHFFFAOYSA-N 2-cyclopropylacetic acid Chemical compound OC(=O)CC1CC1 KVVDRQDTODKIJD-UHFFFAOYSA-N 0.000 description 1
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- GSLTVFIVJMCNBH-UHFFFAOYSA-N 2-isocyanatopropane Chemical compound CC(C)N=C=O GSLTVFIVJMCNBH-UHFFFAOYSA-N 0.000 description 1
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 1
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
- PNFHOXIMSJVSQE-UHFFFAOYSA-N 3-(2,3-difluorophenyl)-5-methyl-2-[1-(7h-purin-6-ylamino)ethyl]quinazolin-4-one Chemical compound N=1C=NC=2NC=NC=2C=1NC(C)C1=NC2=CC=CC(C)=C2C(=O)N1C1=CC=CC(F)=C1F PNFHOXIMSJVSQE-UHFFFAOYSA-N 0.000 description 1
- XLJVEBRFYDUKKP-UHFFFAOYSA-N 3-(2,6-difluorophenyl)-5-methyl-2-[1-(7h-purin-6-ylamino)propyl]quinazolin-4-one Chemical compound N=1C=NC=2NC=NC=2C=1NC(CC)C1=NC2=CC=CC(C)=C2C(=O)N1C1=C(F)C=CC=C1F XLJVEBRFYDUKKP-UHFFFAOYSA-N 0.000 description 1
- IXFNUCHGJGIOGF-UHFFFAOYSA-N 3-(2-chlorophenyl)-2-(7h-purin-6-ylsulfanylmethyl)-8-(trifluoromethyl)quinazolin-4-one Chemical compound FC(F)(F)C1=CC=CC(C2=O)=C1N=C(CSC=1C=3N=CNC=3N=CN=1)N2C1=CC=CC=C1Cl IXFNUCHGJGIOGF-UHFFFAOYSA-N 0.000 description 1
- SBBLBPZNMNHDJR-UHFFFAOYSA-N 3-(2-chlorophenyl)-2-(7h-purin-6-ylsulfanylmethyl)benzo[g]quinazolin-4-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=CC3=CC=CC=C3C=C2N=C1CSC1=NC=NC2=C1N=CN2 SBBLBPZNMNHDJR-UHFFFAOYSA-N 0.000 description 1
- ZSIQRGJFUORDSD-UHFFFAOYSA-N 3-(2-chlorophenyl)-5-(2-morpholin-4-ylethylamino)-2-(7h-purin-6-ylsulfanylmethyl)quinazolin-4-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=C(NCCN3CCOCC3)C=CC=C2N=C1CSC1=NC=NC2=C1N=CN2 ZSIQRGJFUORDSD-UHFFFAOYSA-N 0.000 description 1
- AOFNUITUVSMFAJ-UHFFFAOYSA-N 3-(2-chlorophenyl)-5-(2-phenylmethoxyethoxy)-2-(7h-purin-6-ylsulfanylmethyl)quinazolin-4-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=C(OCCOCC=3C=CC=CC=3)C=CC=C2N=C1CSC1=NC=NC2=C1N=CN2 AOFNUITUVSMFAJ-UHFFFAOYSA-N 0.000 description 1
- BNQLOVCAZBJWHG-UHFFFAOYSA-N 3-(2-chlorophenyl)-5-fluoro-2-[(7h-purin-6-ylamino)methyl]quinazolin-4-one Chemical compound O=C1C=2C(F)=CC=CC=2N=C(CNC=2C=3N=CNC=3N=CN=2)N1C1=CC=CC=C1Cl BNQLOVCAZBJWHG-UHFFFAOYSA-N 0.000 description 1
- JAXIVPLUFZVTPK-UHFFFAOYSA-N 3-(2-chlorophenyl)-5-fluoro-2-[7h-purin-6-yl(sulfanyl)methyl]quinazolin-4-one Chemical compound O=C1C=2C(F)=CC=CC=2N=C(C(S)C=2C=3N=CNC=3N=CN=2)N1C1=CC=CC=C1Cl JAXIVPLUFZVTPK-UHFFFAOYSA-N 0.000 description 1
- TUXLGSGRVBIQMB-UHFFFAOYSA-N 3-(2-chlorophenyl)-5-methoxy-2-(7h-purin-6-ylsulfanylmethyl)quinazolin-4-one Chemical compound O=C1C=2C(OC)=CC=CC=2N=C(CSC=2C=3N=CNC=3N=CN=2)N1C1=CC=CC=C1Cl TUXLGSGRVBIQMB-UHFFFAOYSA-N 0.000 description 1
- JWWJEXRDBLGHGY-UHFFFAOYSA-N 3-(2-chlorophenyl)-5-methyl-2-[7h-purin-6-yl(sulfanyl)methyl]quinazolin-4-one Chemical compound O=C1C=2C(C)=CC=CC=2N=C(C(S)C=2C=3N=CNC=3N=CN=2)N1C1=CC=CC=C1Cl JWWJEXRDBLGHGY-UHFFFAOYSA-N 0.000 description 1
- VQODQUOBNXKKBV-UHFFFAOYSA-N 3-(2-chlorophenyl)-6,7-difluoro-2-[7h-purin-6-yl(sulfanyl)methyl]quinazolin-4-one Chemical compound O=C1C=2C=C(F)C(F)=CC=2N=C(C(S)C=2C=3N=CNC=3N=CN=2)N1C1=CC=CC=C1Cl VQODQUOBNXKKBV-UHFFFAOYSA-N 0.000 description 1
- MKTJBRZFMGOZSK-UHFFFAOYSA-N 3-(2-chlorophenyl)-6,7-dimethoxy-2-[7h-purin-6-yl(sulfanyl)methyl]quinazolin-4-one Chemical compound O=C1C=2C=C(OC)C(OC)=CC=2N=C(C(S)C=2C=3N=CNC=3N=CN=2)N1C1=CC=CC=C1Cl MKTJBRZFMGOZSK-UHFFFAOYSA-N 0.000 description 1
- PVILDBBJNYGRMC-UHFFFAOYSA-N 3-(2-chlorophenyl)-6-fluoro-2-[7h-purin-6-yl(sulfanyl)methyl]quinazolin-4-one Chemical compound O=C1C2=CC(F)=CC=C2N=C(C(S)C=2C=3N=CNC=3N=CN=2)N1C1=CC=CC=C1Cl PVILDBBJNYGRMC-UHFFFAOYSA-N 0.000 description 1
- YGZFWMOZAYEOBQ-UHFFFAOYSA-N 3-(2-chlorophenyl)-6-hydroxy-2-[7h-purin-6-yl(sulfanyl)methyl]quinazolin-4-one Chemical compound O=C1C2=CC(O)=CC=C2N=C(C(S)C=2C=3N=CNC=3N=CN=2)N1C1=CC=CC=C1Cl YGZFWMOZAYEOBQ-UHFFFAOYSA-N 0.000 description 1
- XRLCVUJSEPKNQG-UHFFFAOYSA-N 3-(2-chlorophenyl)-7-nitro-2-[7h-purin-6-yl(sulfanyl)methyl]quinazolin-4-one Chemical compound C=1C([N+](=O)[O-])=CC=C(C2=O)C=1N=C(C(S)C=1C=3N=CNC=3N=CN=1)N2C1=CC=CC=C1Cl XRLCVUJSEPKNQG-UHFFFAOYSA-N 0.000 description 1
- LCYVAKNIYHOWGS-UHFFFAOYSA-N 3-(2-chloropyridin-3-yl)-5-methyl-2-(7h-purin-6-ylsulfanylmethyl)quinazolin-4-one Chemical compound O=C1C=2C(C)=CC=CC=2N=C(CSC=2C=3N=CNC=3N=CN=2)N1C1=CC=CN=C1Cl LCYVAKNIYHOWGS-UHFFFAOYSA-N 0.000 description 1
- PLDXRWBSWYKXMM-UHFFFAOYSA-N 3-(2-fluorophenyl)-5-methyl-2-[7h-purin-6-yl(sulfanyl)methyl]quinazolin-4-one Chemical compound O=C1C=2C(C)=CC=CC=2N=C(C(S)C=2C=3N=CNC=3N=CN=2)N1C1=CC=CC=C1F PLDXRWBSWYKXMM-UHFFFAOYSA-N 0.000 description 1
- PQZIPKRLIODVNY-UHFFFAOYSA-N 3-(3,5-difluorophenyl)-5-methyl-2-[1-(7h-purin-6-ylamino)ethyl]quinazolin-4-one Chemical compound N=1C=NC=2NC=NC=2C=1NC(C)C1=NC2=CC=CC(C)=C2C(=O)N1C1=CC(F)=CC(F)=C1 PQZIPKRLIODVNY-UHFFFAOYSA-N 0.000 description 1
- OSJUTODIQCURGT-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-methyl-2-[1-(7h-purin-6-ylamino)ethyl]quinazolin-4-one Chemical compound N=1C=NC=2NC=NC=2C=1NC(C)C1=NC2=CC=CC(C)=C2C(=O)N1C1=CC=CC(Cl)=C1 OSJUTODIQCURGT-UHFFFAOYSA-N 0.000 description 1
- DDYUBCCTNHWSQM-UHFFFAOYSA-N 3-(3-cyclopentyloxy-4-methoxyphenyl)-3-(1,3-dioxoisoindol-2-yl)propanamide Chemical compound COC1=CC=C(C(CC(N)=O)N2C(C3=CC=CC=C3C2=O)=O)C=C1OC1CCCC1 DDYUBCCTNHWSQM-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- BNXFTDGQFXVLIY-UHFFFAOYSA-N 3-benzyl-5-methoxy-2-(7h-purin-6-ylsulfanylmethyl)quinazolin-4-one Chemical compound O=C1C=2C(OC)=CC=CC=2N=C(CSC=2C=3N=CNC=3N=CN=2)N1CC1=CC=CC=C1 BNXFTDGQFXVLIY-UHFFFAOYSA-N 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- SDJTYJFRNCKHPW-UHFFFAOYSA-N 3-cyclohexyl-5-methyl-2-(7h-purin-6-ylsulfanylmethyl)quinazolin-4-one Chemical compound O=C1C=2C(C)=CC=CC=2N=C(CSC=2C=3N=CNC=3N=CN=2)N1C1CCCCC1 SDJTYJFRNCKHPW-UHFFFAOYSA-N 0.000 description 1
- CJHRMVHGYKCUFB-UHFFFAOYSA-N 3-cyclopentyl-5-methyl-2-(7h-purin-6-ylsulfanylmethyl)quinazolin-4-one Chemical compound O=C1C=2C(C)=CC=CC=2N=C(CSC=2C=3N=CNC=3N=CN=2)N1C1CCCC1 CJHRMVHGYKCUFB-UHFFFAOYSA-N 0.000 description 1
- TZWOWRUGGYZPDH-UHFFFAOYSA-N 3-cyclopropyl-5-methyl-2-(7h-purin-6-ylsulfanylmethyl)quinazolin-4-one Chemical compound O=C1C=2C(C)=CC=CC=2N=C(CSC=2C=3N=CNC=3N=CN=2)N1C1CC1 TZWOWRUGGYZPDH-UHFFFAOYSA-N 0.000 description 1
- CPYNQFQDUZSGQX-UHFFFAOYSA-N 3-methyl-4-[5-methyl-4-oxo-2-(7h-purin-6-ylsulfanylmethyl)quinazolin-3-yl]benzoic acid Chemical compound CC1=CC(C(O)=O)=CC=C1N1C(=O)C2=C(C)C=CC=C2N=C1CSC1=NC=NC2=C1N=CN2 CPYNQFQDUZSGQX-UHFFFAOYSA-N 0.000 description 1
- ROIASNIEFPZNJL-UHFFFAOYSA-N 3-phenyl-2-[1-(7h-purin-6-ylamino)propyl]quinazolin-4-one Chemical compound N=1C=NC=2NC=NC=2C=1NC(CC)C1=NC2=CC=CC=C2C(=O)N1C1=CC=CC=C1 ROIASNIEFPZNJL-UHFFFAOYSA-N 0.000 description 1
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 1
- LIXBJWRFCNRAPA-NSHDSACASA-N 4-[(1r)-2-(tert-butylamino)-1-hydroxyethyl]-3-chlorophenol Chemical compound CC(C)(C)NC[C@H](O)C1=CC=C(O)C=C1Cl LIXBJWRFCNRAPA-NSHDSACASA-N 0.000 description 1
- UTUUPXBCDMQYRR-HSZRJFAPSA-N 4-[(2r)-2-(3-cyclopentyloxy-4-methoxyphenyl)-2-phenylethyl]pyridine Chemical compound COC1=CC=C([C@H](CC=2C=CN=CC=2)C=2C=CC=CC=2)C=C1OC1CCCC1 UTUUPXBCDMQYRR-HSZRJFAPSA-N 0.000 description 1
- RTLJQOLVPIGICL-UHFFFAOYSA-N 4-[2-(tert-butylamino)-1-hydroxyethyl]-2-(methylsulfonylmethyl)phenol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CS(C)(=O)=O)=C1 RTLJQOLVPIGICL-UHFFFAOYSA-N 0.000 description 1
- LIXBJWRFCNRAPA-UHFFFAOYSA-N 4-[2-(tert-butylamino)-1-hydroxyethyl]-3-chlorophenol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C=C1Cl LIXBJWRFCNRAPA-UHFFFAOYSA-N 0.000 description 1
- SHBAZPSOJMNBQU-UHFFFAOYSA-N 4-[2-[3-(2-acetamido-4,5-dihydro-[1,3]thiazolo[4,5-h]quinazolin-8-yl)-4-chlorophenyl]ethynyl]-n-propan-2-ylpiperidine-1-carboxamide Chemical compound C1CN(C(=O)NC(C)C)CCC1C#CC1=CC=C(Cl)C(C=2N=C3C=4SC(NC(C)=O)=NC=4CCC3=CN=2)=C1 SHBAZPSOJMNBQU-UHFFFAOYSA-N 0.000 description 1
- KBCXRHLBSWOGJD-UHFFFAOYSA-N 4-ethynyl-1-propan-2-ylpiperidin-4-ol Chemical compound CC(C)N1CCC(O)(C#C)CC1 KBCXRHLBSWOGJD-UHFFFAOYSA-N 0.000 description 1
- OYEANGLUIDHEPS-UHFFFAOYSA-N 4-ethynyl-1-propan-2-ylpiperidine Chemical compound CC(C)N1CCC(C#C)CC1 OYEANGLUIDHEPS-UHFFFAOYSA-N 0.000 description 1
- YKQPCMHUDFIVDS-UHFFFAOYSA-N 4-ethynyl-4-methoxy-1-methylpiperidine Chemical compound COC1(C#C)CCN(C)CC1 YKQPCMHUDFIVDS-UHFFFAOYSA-N 0.000 description 1
- LLBZPESJRQGYMB-UHFFFAOYSA-N 4-one Natural products O1C(C(=O)CC)CC(C)C11C2(C)CCC(C3(C)C(C(C)(CO)C(OC4C(C(O)C(O)C(COC5C(C(O)C(O)CO5)OC5C(C(OC6C(C(O)C(O)C(CO)O6)O)C(O)C(CO)O5)OC5C(C(O)C(O)C(C)O5)O)O4)O)CC3)CC3)=C3C2(C)CC1 LLBZPESJRQGYMB-UHFFFAOYSA-N 0.000 description 1
- QSXVNFUQRSMEBI-UHFFFAOYSA-N 5-(2-chlorophenyl)-3-(dimethylamino)-2-(7h-purin-6-ylsulfanylmethyl)quinazolin-4-one Chemical compound C=12C(=O)N(N(C)C)C(CSC=3C=4N=CNC=4N=CN=3)=NC2=CC=CC=1C1=CC=CC=C1Cl QSXVNFUQRSMEBI-UHFFFAOYSA-N 0.000 description 1
- LSLYOANBFKQKPT-DIFFPNOSSA-N 5-[(1r)-1-hydroxy-2-[[(2r)-1-(4-hydroxyphenyl)propan-2-yl]amino]ethyl]benzene-1,3-diol Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(O)C=C(O)C=1)C1=CC=C(O)C=C1 LSLYOANBFKQKPT-DIFFPNOSSA-N 0.000 description 1
- JGTDVIHDYGJHOI-UHFFFAOYSA-N 5-chloro-3-(2-chlorophenyl)-2-[(7h-purin-6-ylamino)methyl]quinazolin-4-one Chemical compound ClC1=CC=CC=C1N1C(=O)C2=C(Cl)C=CC=C2N=C1CNC1=NC=NC2=C1N=CN2 JGTDVIHDYGJHOI-UHFFFAOYSA-N 0.000 description 1
- VXQMDXAVANXDGQ-UHFFFAOYSA-N 5-chloro-3-(2-chlorophenyl)-2-[7h-purin-6-yl(sulfanyl)methyl]quinazolin-4-one Chemical compound N=1C=NC=2NC=NC=2C=1C(S)C1=NC2=CC=CC(Cl)=C2C(=O)N1C1=CC=CC=C1Cl VXQMDXAVANXDGQ-UHFFFAOYSA-N 0.000 description 1
- CEEVAKGSIWXKBC-UHFFFAOYSA-N 5-chloro-3-(2-fluorophenyl)-2-[(7h-purin-6-ylamino)methyl]quinazolin-4-one Chemical compound FC1=CC=CC=C1N1C(=O)C2=C(Cl)C=CC=C2N=C1CNC1=NC=NC2=C1N=CN2 CEEVAKGSIWXKBC-UHFFFAOYSA-N 0.000 description 1
- JIYPRDGRRKVUHV-UHFFFAOYSA-N 5-chloro-3-(2-fluorophenyl)-2-[7h-purin-6-yl(sulfanyl)methyl]quinazolin-4-one Chemical compound FC1=CC=CC=C1N1C(=O)C2=C(Cl)C=CC=C2N=C1C(S)C1=NC=NC2=C1N=CN2 JIYPRDGRRKVUHV-UHFFFAOYSA-N 0.000 description 1
- KGKAIJHVJXRTIS-UHFFFAOYSA-N 5-chloro-3-(2-methoxyphenyl)-2-[7h-purin-6-yl(sulfanyl)methyl]quinazolin-4-one Chemical compound COC1=CC=CC=C1N1C(=O)C2=C(Cl)C=CC=C2N=C1C(S)C1=NC=NC2=C1N=CN2 KGKAIJHVJXRTIS-UHFFFAOYSA-N 0.000 description 1
- BJKBTSPAISPLCZ-UHFFFAOYSA-N 5-chloro-3-(2-methylphenyl)-2-[(7h-purin-6-ylamino)methyl]quinazolin-4-one Chemical compound CC1=CC=CC=C1N1C(=O)C2=C(Cl)C=CC=C2N=C1CNC1=NC=NC2=C1N=CN2 BJKBTSPAISPLCZ-UHFFFAOYSA-N 0.000 description 1
- VDOLSOHFRBGGER-UHFFFAOYSA-N 5-chloro-3-(2-phenylphenyl)-2-(7h-purin-6-ylsulfanylmethyl)quinazolin-4-one Chemical compound O=C1C=2C(Cl)=CC=CC=2N=C(CSC=2C=3N=CNC=3N=CN=2)N1C1=CC=CC=C1C1=CC=CC=C1 VDOLSOHFRBGGER-UHFFFAOYSA-N 0.000 description 1
- BVUBLIHUYSRSFE-UHFFFAOYSA-N 5-fluoro-3-phenyl-2-[1-(7h-purin-6-ylamino)ethyl]quinazolin-4-one Chemical compound N=1C=NC=2NC=NC=2C=1NC(C)C1=NC2=CC=CC(F)=C2C(=O)N1C1=CC=CC=C1 BVUBLIHUYSRSFE-UHFFFAOYSA-N 0.000 description 1
- IFSDAJWBUCMOAH-UHFFFAOYSA-N 5-fluoro-3-phenyl-2-[1-(7h-purin-6-ylamino)propyl]quinazolin-4-one Chemical compound N=1C=NC=2NC=NC=2C=1NC(CC)C1=NC2=CC=CC(F)=C2C(=O)N1C1=CC=CC=C1 IFSDAJWBUCMOAH-UHFFFAOYSA-N 0.000 description 1
- LQUIGYFXMNCNBY-UHFFFAOYSA-N 5-methyl-2-[(1-methylimidazol-2-yl)sulfanylmethyl]-3-(2-methylphenyl)quinazolin-4-one Chemical compound CC1=CC=CC=C1N1C(=O)C2=C(C)C=CC=C2N=C1CSC1=NC=CN1C LQUIGYFXMNCNBY-UHFFFAOYSA-N 0.000 description 1
- AHLCCIKVWYSPKZ-UHFFFAOYSA-N 5-methyl-2-[(2-methyl-6-oxo-3h-purin-7-yl)methyl]-3-(2-methylphenyl)quinazolin-4-one Chemical compound CC1=CC=CC=C1N1C(=O)C2=C(C)C=CC=C2N=C1CN1C(C(=O)NC(C)=N2)=C2N=C1 AHLCCIKVWYSPKZ-UHFFFAOYSA-N 0.000 description 1
- JSJQJMOTACJJIC-UHFFFAOYSA-N 5-methyl-2-[(2-methyl-6-oxo-3h-purin-9-yl)methyl]-3-(2-methylphenyl)quinazolin-4-one Chemical compound CC1=CC=CC=C1N1C(=O)C2=C(C)C=CC=C2N=C1CN1C(N=C(C)NC2=O)=C2N=C1 JSJQJMOTACJJIC-UHFFFAOYSA-N 0.000 description 1
- UFPVKWSIZDJDCQ-UHFFFAOYSA-N 5-methyl-2-[[6-(methylamino)purin-9-yl]methyl]-3-(2-methylphenyl)quinazolin-4-one Chemical compound C1=NC=2C(NC)=NC=NC=2N1CC1=NC2=CC=CC(C)=C2C(=O)N1C1=CC=CC=C1C UFPVKWSIZDJDCQ-UHFFFAOYSA-N 0.000 description 1
- UDMCUVNNNQKWSO-UHFFFAOYSA-N 5-methyl-3-(2-methylphenyl)-2-(7h-purin-6-ylsulfanylmethyl)quinazolin-4-one Chemical compound CC1=CC=CC=C1N1C(=O)C2=C(C)C=CC=C2N=C1CSC1=NC=NC2=C1N=CN2 UDMCUVNNNQKWSO-UHFFFAOYSA-N 0.000 description 1
- WPYVXMUPYRJJDY-UHFFFAOYSA-N 5-methyl-3-(2-methylphenyl)-2-(purin-7-ylmethyl)quinazolin-4-one Chemical compound CC1=CC=CC=C1N1C(=O)C2=C(C)C=CC=C2N=C1CN1C2=CN=CN=C2N=C1 WPYVXMUPYRJJDY-UHFFFAOYSA-N 0.000 description 1
- XGBJKHZWQCGCDK-UHFFFAOYSA-N 5-methyl-3-(2-methylphenyl)-2-(purin-9-ylmethyl)quinazolin-4-one Chemical compound CC1=CC=CC=C1N1C(=O)C2=C(C)C=CC=C2N=C1CN1C2=NC=NC=C2N=C1 XGBJKHZWQCGCDK-UHFFFAOYSA-N 0.000 description 1
- GVNMCFOHCUFLSY-UHFFFAOYSA-N 5-methyl-3-(2-methylphenyl)-2-[(2-methylsulfanyl-7h-purin-6-yl)sulfanylmethyl]quinazolin-4-one Chemical compound C=12N=CNC2=NC(SC)=NC=1SCC1=NC2=CC=CC(C)=C2C(=O)N1C1=CC=CC=C1C GVNMCFOHCUFLSY-UHFFFAOYSA-N 0.000 description 1
- PLJJRCGFQCBOOA-UHFFFAOYSA-N 5-methyl-3-(2-methylphenyl)-2-[(2-oxo-1h-pyrimidin-6-yl)sulfanylmethyl]quinazolin-4-one Chemical compound CC1=CC=CC=C1N1C(=O)C2=C(C)C=CC=C2N=C1CSC1=NC(=O)NC=C1 PLJJRCGFQCBOOA-UHFFFAOYSA-N 0.000 description 1
- ZJZMWKJHZKBLAD-UHFFFAOYSA-N 5-methyl-3-(2-methylphenyl)-2-[(2-oxo-3,7-dihydropurin-6-yl)sulfanylmethyl]quinazolin-4-one Chemical compound CC1=CC=CC=C1N1C(=O)C2=C(C)C=CC=C2N=C1CSC1=NC(O)=NC2=C1N=CN2 ZJZMWKJHZKBLAD-UHFFFAOYSA-N 0.000 description 1
- GIMZHZAQQLFKDY-UHFFFAOYSA-N 5-methyl-3-(2-methylphenyl)-2-[(7h-purin-6-ylamino)methyl]quinazolin-4-one Chemical compound CC1=CC=CC=C1N1C(=O)C2=C(C)C=CC=C2N=C1CNC1=NC=NC2=C1N=CN2 GIMZHZAQQLFKDY-UHFFFAOYSA-N 0.000 description 1
- MWZGQBFHDPTVTF-UHFFFAOYSA-N 5-methyl-3-(2-methylphenyl)-2-[(9-methylpurin-6-yl)sulfanylmethyl]quinazolin-4-one Chemical compound CC1=CC=CC=C1N1C(=O)C2=C(C)C=CC=C2N=C1CSC1=NC=NC2=C1N=CN2C MWZGQBFHDPTVTF-UHFFFAOYSA-N 0.000 description 1
- NILGZRIBALJAAD-UHFFFAOYSA-N 5-methyl-3-(2-methylphenyl)-2-[1-(7h-purin-6-ylamino)ethyl]quinazolin-4-one Chemical compound N=1C=NC=2NC=NC=2C=1NC(C)C1=NC2=CC=CC(C)=C2C(=O)N1C1=CC=CC=C1C NILGZRIBALJAAD-UHFFFAOYSA-N 0.000 description 1
- JIOWNSNEPALFLU-UHFFFAOYSA-N 5-methyl-3-(2-methylphenyl)-2-[1-(7h-purin-6-ylamino)propyl]quinazolin-4-one Chemical compound N=1C=NC=2NC=NC=2C=1NC(CC)C1=NC2=CC=CC(C)=C2C(=O)N1C1=CC=CC=C1C JIOWNSNEPALFLU-UHFFFAOYSA-N 0.000 description 1
- RXJGCQUSAVHNEZ-UHFFFAOYSA-N 5-methyl-3-(2-methylphenyl)-2-[2-phenylmethoxy-1-(7h-purin-6-ylamino)ethyl]quinazolin-4-one Chemical compound CC1=CC=CC=C1N1C(=O)C2=C(C)C=CC=C2N=C1C(NC=1C=2N=CNC=2N=CN=1)COCC1=CC=CC=C1 RXJGCQUSAVHNEZ-UHFFFAOYSA-N 0.000 description 1
- FFUMMBVLZZCIIV-UHFFFAOYSA-N 5-methyl-3-(2-methylpropyl)-2-(7h-purin-6-ylsulfanylmethyl)quinazolin-4-one Chemical compound C1=CC(C)=C2C(=O)N(CC(C)C)C(CSC=3C=4N=CNC=4N=CN=3)=NC2=C1 FFUMMBVLZZCIIV-UHFFFAOYSA-N 0.000 description 1
- CZYNMDYJQOHKDV-UHFFFAOYSA-N 5-methyl-3-[(4-nitrophenyl)methyl]-2-(7h-purin-6-ylsulfanylmethyl)quinazolin-4-one Chemical compound O=C1C=2C(C)=CC=CC=2N=C(CSC=2C=3N=CNC=3N=CN=2)N1CC1=CC=C([N+]([O-])=O)C=C1 CZYNMDYJQOHKDV-UHFFFAOYSA-N 0.000 description 1
- MWVOAOANSHKHDU-UHFFFAOYSA-N 5-methyl-3-phenyl-2-[(7h-purin-6-ylamino)methyl]quinazolin-4-one Chemical compound O=C1C=2C(C)=CC=CC=2N=C(CNC=2C=3N=CNC=3N=CN=2)N1C1=CC=CC=C1 MWVOAOANSHKHDU-UHFFFAOYSA-N 0.000 description 1
- PFJKYYFKFHTRQY-UHFFFAOYSA-N 5-methyl-3-phenyl-2-[1-(7h-purin-6-ylamino)ethyl]quinazolin-4-one Chemical compound N=1C=NC=2NC=NC=2C=1NC(C)C1=NC2=CC=CC(C)=C2C(=O)N1C1=CC=CC=C1 PFJKYYFKFHTRQY-UHFFFAOYSA-N 0.000 description 1
- ZLLOWHFKKIOINR-UHFFFAOYSA-N 5-phenyl-1,3-thiazole Chemical class S1C=NC=C1C1=CC=CC=C1 ZLLOWHFKKIOINR-UHFFFAOYSA-N 0.000 description 1
- PEULIOAFYDSNOQ-UHFFFAOYSA-N 6-bromo-3-(2-chlorophenyl)-2-[7h-purin-6-yl(sulfanyl)methyl]quinazolin-4-one Chemical compound N=1C=NC=2NC=NC=2C=1C(S)C1=NC2=CC=C(Br)C=C2C(=O)N1C1=CC=CC=C1Cl PEULIOAFYDSNOQ-UHFFFAOYSA-N 0.000 description 1
- KHPHPCMNPOCRFY-UHFFFAOYSA-N 6-chloro-3-(2-chlorophenyl)-2-[7h-purin-6-yl(sulfanyl)methyl]quinazolin-4-one Chemical compound N=1C=NC=2NC=NC=2C=1C(S)C1=NC2=CC=C(Cl)C=C2C(=O)N1C1=CC=CC=C1Cl KHPHPCMNPOCRFY-UHFFFAOYSA-N 0.000 description 1
- ORPWNMZXEOGJSM-UHFFFAOYSA-N 6-fluoro-3-(3-fluorophenyl)-2-[1-(7h-purin-6-ylamino)ethyl]quinazolin-4-one Chemical compound N=1C=NC=2NC=NC=2C=1NC(C)C1=NC2=CC=C(F)C=C2C(=O)N1C1=CC=CC(F)=C1 ORPWNMZXEOGJSM-UHFFFAOYSA-N 0.000 description 1
- DOCINCLJNAXZQF-UHFFFAOYSA-N 6-fluoro-3-phenyl-2-[1-(7h-purin-6-ylamino)ethyl]quinazolin-4-one Chemical compound N=1C=NC=2NC=NC=2C=1NC(C)C1=NC2=CC=C(F)C=C2C(=O)N1C1=CC=CC=C1 DOCINCLJNAXZQF-UHFFFAOYSA-N 0.000 description 1
- DHSSDEDRBUKTQY-UHFFFAOYSA-N 6-prop-2-enyl-4,5,7,8-tetrahydrothiazolo[4,5-d]azepin-2-amine Chemical compound C1CN(CC=C)CCC2=C1N=C(N)S2 DHSSDEDRBUKTQY-UHFFFAOYSA-N 0.000 description 1
- ULIWQOIKHAJQQB-UHFFFAOYSA-N 8-chloro-3-(2-chlorophenyl)-2-[7h-purin-6-yl(sulfanyl)methyl]quinazolin-4-one Chemical compound N=1C=NC=2NC=NC=2C=1C(S)C1=NC2=C(Cl)C=CC=C2C(=O)N1C1=CC=CC=C1Cl ULIWQOIKHAJQQB-UHFFFAOYSA-N 0.000 description 1
- HSSOKKMHIZSFTR-UHFFFAOYSA-N 8-fluoro-6-(hydroxymethyl)-4h-1,4-benzoxazin-3-one Chemical compound O1CC(=O)NC2=CC(CO)=CC(F)=C21 HSSOKKMHIZSFTR-UHFFFAOYSA-N 0.000 description 1
- ZULHADSAMXFQOG-UHFFFAOYSA-N 9-hydroxyfluorene-9-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)(O)C3=CC=CC=C3C2=C1.C1=CC=C2C(C(=O)O)(O)C3=CC=CC=C3C2=C1 ZULHADSAMXFQOG-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 description 1
- 201000004384 Alopecia Diseases 0.000 description 1
- 206010002199 Anaphylactic shock Diseases 0.000 description 1
- 208000033116 Asbestos intoxication Diseases 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- MBUVEWMHONZEQD-UHFFFAOYSA-N Azeptin Chemical compound C1CN(C)CCCC1N1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 MBUVEWMHONZEQD-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- AHPQVFNRLRHXDO-LMOVPXPDSA-N BrC1=CC=C(CN2C(C[C@@H](C2)C2=C(C=C(C=C2)OC)OC2CCCC2)=O)C=C1.C(C)(C)C=1C(=C(C(=O)N)C=CC1)C(C)C Chemical compound BrC1=CC=C(CN2C(C[C@@H](C2)C2=C(C=C(C=C2)OC)OC2CCCC2)=O)C=C1.C(C)(C)C=1C(=C(C(=O)N)C=CC1)C(C)C AHPQVFNRLRHXDO-LMOVPXPDSA-N 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- 206010066091 Bronchial Hyperreactivity Diseases 0.000 description 1
- VOVIALXJUBGFJZ-KWVAZRHASA-N Budesonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(CCC)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O VOVIALXJUBGFJZ-KWVAZRHASA-N 0.000 description 1
- ZFYQSNZVCQRVFL-UHFFFAOYSA-N C1(CCCC1)N1N=C(C2=C1C=1N(CC2)C(=NN1)C=1SC=CC1)CC.C(C)(=O)O Chemical compound C1(CCCC1)N1N=C(C2=C1C=1N(CC2)C(=NN1)C=1SC=CC1)CC.C(C)(=O)O ZFYQSNZVCQRVFL-UHFFFAOYSA-N 0.000 description 1
- KORNTPPJEAJQIU-KJXAQDMKSA-N Cabaser Chemical compound C1=CC([C@H]2C[C@H](CN(CC=C)[C@@H]2C2)C(=O)N(CCCN(C)C)C(=O)NCC)=C3C2=CNC3=C1 KORNTPPJEAJQIU-KJXAQDMKSA-N 0.000 description 1
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical class NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 206010007572 Cardiac hypertrophy Diseases 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 229920000623 Cellulose acetate phthalate Polymers 0.000 description 1
- ZKLPARSLTMPFCP-UHFFFAOYSA-N Cetirizine Chemical compound C1CN(CCOCC(=O)O)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 ZKLPARSLTMPFCP-UHFFFAOYSA-N 0.000 description 1
- LUKZNWIVRBCLON-GXOBDPJESA-N Ciclesonide Chemical compound C1([C@H]2O[C@@]3([C@H](O2)C[C@@H]2[C@@]3(C[C@H](O)[C@@H]3[C@@]4(C)C=CC(=O)C=C4CC[C@H]32)C)C(=O)COC(=O)C(C)C)CCCCC1 LUKZNWIVRBCLON-GXOBDPJESA-N 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
- WYVWPGYDWJHKFK-UHFFFAOYSA-N ClC=1C=C(C=CC1F)NC1=NC=NC2=CC(=C(C=C12)OC1CCN(CC1)S(=O)(=O)C)OC.N1=CN=CC2=CC=CC=C12 Chemical compound ClC=1C=C(C=CC1F)NC1=NC=NC2=CC(=C(C=C12)OC1CCN(CC1)S(=O)(=O)C)OC.N1=CN=CC2=CC=CC=C12 WYVWPGYDWJHKFK-UHFFFAOYSA-N 0.000 description 1
- 206010009944 Colon cancer Diseases 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- UDIPTWFVPPPURJ-UHFFFAOYSA-M Cyclamate Chemical compound [Na+].[O-]S(=O)(=O)NC1CCCCC1 UDIPTWFVPPPURJ-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-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
- QEVGZEDELICMKH-UHFFFAOYSA-N Diglycolic acid Chemical compound OC(=O)COCC(O)=O QEVGZEDELICMKH-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical class OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 241001331845 Equus asinus x caballus Species 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 description 1
- GXAMYUGOODKVRM-UHFFFAOYSA-N Flurecol Chemical compound C1=CC=C2C(C(=O)O)(O)C3=CC=CC=C3C2=C1 GXAMYUGOODKVRM-UHFFFAOYSA-N 0.000 description 1
- 206010017533 Fungal infection Diseases 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 description 1
- ZWZWYGMENQVNFU-UHFFFAOYSA-N Glycerophosphorylserin Natural products OC(=O)C(N)COP(O)(=O)OCC(O)CO ZWZWYGMENQVNFU-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 108010081348 HRT1 protein Hairy Proteins 0.000 description 1
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- SQUHHTBVTRBESD-UHFFFAOYSA-N Hexa-Ac-myo-Inositol Natural products CC(=O)OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O SQUHHTBVTRBESD-UHFFFAOYSA-N 0.000 description 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 1
- 208000029523 Interstitial Lung disease Diseases 0.000 description 1
- HUYWAWARQUIQLE-UHFFFAOYSA-N Isoetharine Chemical compound CC(C)NC(CC)C(O)C1=CC=C(O)C(O)=C1 HUYWAWARQUIQLE-UHFFFAOYSA-N 0.000 description 1
- PWWVAXIEGOYWEE-UHFFFAOYSA-N Isophenergan Chemical compound C1=CC=C2N(CC(C)N(C)C)C3=CC=CC=C3SC2=C1 PWWVAXIEGOYWEE-UHFFFAOYSA-N 0.000 description 1
- ZCVMWBYGMWKGHF-UHFFFAOYSA-N Ketotifene Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2CC(=O)C2=C1C=CS2 ZCVMWBYGMWKGHF-UHFFFAOYSA-N 0.000 description 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
- OCJYIGYOJCODJL-UHFFFAOYSA-N Meclizine Chemical compound CC1=CC=CC(CN2CCN(CC2)C(C=2C=CC=CC=2)C=2C=CC(Cl)=CC=2)=C1 OCJYIGYOJCODJL-UHFFFAOYSA-N 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- PVLJETXTTWAYEW-UHFFFAOYSA-N Mizolastine Chemical compound N=1C=CC(=O)NC=1N(C)C(CC1)CCN1C1=NC2=CC=CC=C2N1CC1=CC=C(F)C=C1 PVLJETXTTWAYEW-UHFFFAOYSA-N 0.000 description 1
- UCHDWCPVSPXUMX-TZIWLTJVSA-N Montelukast Chemical compound CC(C)(O)C1=CC=CC=C1CC[C@H](C=1C=C(\C=C\C=2N=C3C=C(Cl)C=CC3=CC=2)C=CC=1)SCC1(CC(O)=O)CC1 UCHDWCPVSPXUMX-TZIWLTJVSA-N 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- JAUOIFJMECXRGI-UHFFFAOYSA-N Neoclaritin Chemical compound C=1C(Cl)=CC=C2C=1CCC1=CC=CN=C1C2=C1CCNCC1 JAUOIFJMECXRGI-UHFFFAOYSA-N 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- AQLLBJAXUCIJSR-UHFFFAOYSA-N OC(=O)C[Na] Chemical compound OC(=O)C[Na] AQLLBJAXUCIJSR-UHFFFAOYSA-N 0.000 description 1
- LKYCBBXQWKORQS-UHFFFAOYSA-N OC=1C=C(C2=C(NC(CO2)=O)C1)C(CNC(CC1=CC=C(C=C1)OC)(C)C)O.C(C)O Chemical compound OC=1C=C(C2=C(NC(CO2)=O)C1)C(CNC(CC1=CC=C(C=C1)OC)(C)C)O.C(C)O LKYCBBXQWKORQS-UHFFFAOYSA-N 0.000 description 1
- 206010033078 Otitis media Diseases 0.000 description 1
- 101150037263 PIP2 gene Proteins 0.000 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- 108091000080 Phosphotransferase Proteins 0.000 description 1
- VQDBNKDJNJQRDG-UHFFFAOYSA-N Pirbuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=N1 VQDBNKDJNJQRDG-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- BPZSYCZIITTYBL-YJYMSZOUSA-N R-Formoterol Chemical compound C1=CC(OC)=CC=C1C[C@@H](C)NC[C@H](O)C1=CC=C(O)C(NC=O)=C1 BPZSYCZIITTYBL-YJYMSZOUSA-N 0.000 description 1
- 206010063837 Reperfusion injury Diseases 0.000 description 1
- BKRGVLQUQGGVSM-KBXCAEBGSA-N Revanil Chemical compound C1=CC(C=2[C@H](N(C)C[C@H](C=2)NC(=O)N(CC)CC)C2)=C3C2=CNC3=C1 BKRGVLQUQGGVSM-KBXCAEBGSA-N 0.000 description 1
- RUOGJYKOQBFJIG-UHFFFAOYSA-N SCH-351591 Chemical compound C12=CC=C(C(F)(F)F)N=C2C(OC)=CC=C1C(=O)NC1=C(Cl)C=[N+]([O-])C=C1Cl RUOGJYKOQBFJIG-UHFFFAOYSA-N 0.000 description 1
- 101100262439 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) UBA2 gene Proteins 0.000 description 1
- VPMWDFRZSIMDKW-YJYMSZOUSA-N Salmefamol Chemical compound C1=CC(OC)=CC=C1C[C@@H](C)NC[C@H](O)C1=CC=C(O)C(CO)=C1 VPMWDFRZSIMDKW-YJYMSZOUSA-N 0.000 description 1
- FIMXSEMBHGTNKT-UHFFFAOYSA-N Scopine Natural products CN1C2CC(O)CC1C1C2O1 FIMXSEMBHGTNKT-UHFFFAOYSA-N 0.000 description 1
- GIIZNNXWQWCKIB-UHFFFAOYSA-N Serevent Chemical compound C1=C(O)C(CO)=CC(C(O)CNCCCCCCOCCCCC=2C=CC=CC=2)=C1 GIIZNNXWQWCKIB-UHFFFAOYSA-N 0.000 description 1
- 229920001800 Shellac Polymers 0.000 description 1
- 201000010001 Silicosis Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 241000256251 Spodoptera frugiperda Species 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- JOAHPSVPXZTVEP-YXJHDRRASA-N Terguride Chemical compound C1=CC([C@H]2C[C@@H](CN(C)[C@@H]2C2)NC(=O)N(CC)CC)=C3C2=CNC3=C1 JOAHPSVPXZTVEP-YXJHDRRASA-N 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 description 1
- UKNGDQSYPNBJAO-UHFFFAOYSA-N Tiaramide hydrochloride Chemical compound Cl.C1CN(CCO)CCN1C(=O)CN1C(=O)SC2=CC=C(Cl)C=C21 UKNGDQSYPNBJAO-UHFFFAOYSA-N 0.000 description 1
- 206010044248 Toxic shock syndrome Diseases 0.000 description 1
- QKDLQFSLLCQTOH-UHFFFAOYSA-N Trichodonin Natural products C1C(O)C2C3(COC(=O)C)C(C=O)C(C)(C)CCC3OC(=O)C22C(=O)C(=C)C1C2 QKDLQFSLLCQTOH-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- YEEZWCHGZNKEEK-UHFFFAOYSA-N Zafirlukast Chemical compound COC1=CC(C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C)=CC=C1CC(C1=C2)=CN(C)C1=CC=C2NC(=O)OC1CCCC1 YEEZWCHGZNKEEK-UHFFFAOYSA-N 0.000 description 1
- ANGKOCUUWGHLCE-HKUYNNGSSA-N [(3s)-1,1-dimethylpyrrolidin-1-ium-3-yl] (2r)-2-cyclopentyl-2-hydroxy-2-phenylacetate Chemical class C1[N+](C)(C)CC[C@@H]1OC(=O)[C@](O)(C=1C=CC=CC=1)C1CCCC1 ANGKOCUUWGHLCE-HKUYNNGSSA-N 0.000 description 1
- CDKNUFNIFGPFSF-AYVLZSQQSA-N [(8s,9s,10r,11s,13s,14s,17r)-11-hydroxy-10,13-dimethyl-3-oxo-17-(2-propanoylsulfanylacetyl)-2,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-17-yl] butanoate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)CSC(=O)CC)(OC(=O)CCC)[C@@]1(C)C[C@@H]2O CDKNUFNIFGPFSF-AYVLZSQQSA-N 0.000 description 1
- CPKCLVMYCBRHQP-UHFFFAOYSA-N [3-(2-chlorophenyl)-5-fluoro-4-oxoquinazolin-2-yl]methyl 6-aminopurine-9-carboxylate Chemical compound C1=NC=2C(N)=NC=NC=2N1C(=O)OCC1=NC2=CC=CC(F)=C2C(=O)N1C1=CC=CC=C1Cl CPKCLVMYCBRHQP-UHFFFAOYSA-N 0.000 description 1
- YPFLFUJKZDAXRA-UHFFFAOYSA-N [3-(carbamoylamino)-2-(2,4-dichlorobenzoyl)-1-benzofuran-6-yl] methanesulfonate Chemical compound O1C2=CC(OS(=O)(=O)C)=CC=C2C(NC(N)=O)=C1C(=O)C1=CC=C(Cl)C=C1Cl YPFLFUJKZDAXRA-UHFFFAOYSA-N 0.000 description 1
- WKHOPHIMYDJVSA-UHFFFAOYSA-N [3-[2-(tert-butylamino)-1-hydroxyethyl]-5-(2-methylpropanoyloxy)phenyl] 2-methylpropanoate Chemical compound CC(C)C(=O)OC1=CC(OC(=O)C(C)C)=CC(C(O)CNC(C)(C)C)=C1 WKHOPHIMYDJVSA-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 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
- 230000003044 adaptive effect Effects 0.000 description 1
- 201000000028 adult respiratory distress syndrome Diseases 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 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
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000001078 anti-cholinergic effect Effects 0.000 description 1
- 238000011861 anti-inflammatory therapy Methods 0.000 description 1
- 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 description 1
- 229960001692 arformoterol Drugs 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 230000002917 arthritic effect Effects 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 206010003441 asbestosis Diseases 0.000 description 1
- 229950006944 atizoram Drugs 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229960004574 azelastine Drugs 0.000 description 1
- 229960003060 bambuterol Drugs 0.000 description 1
- ANZXOIAKUNOVQU-UHFFFAOYSA-N bambuterol Chemical compound CN(C)C(=O)OC1=CC(OC(=O)N(C)C)=CC(C(O)CNC(C)(C)C)=C1 ANZXOIAKUNOVQU-UHFFFAOYSA-N 0.000 description 1
- 229960002526 bamipine Drugs 0.000 description 1
- VZSXTYKGYWISGQ-UHFFFAOYSA-N bamipine Chemical compound C1CN(C)CCC1N(C=1C=CC=CC=1)CC1=CC=CC=C1 VZSXTYKGYWISGQ-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229940092705 beclomethasone Drugs 0.000 description 1
- NBMKJKDGKREAPL-DVTGEIKXSA-N beclomethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O NBMKJKDGKREAPL-DVTGEIKXSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 150000005130 benzoxazines Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229960002537 betamethasone Drugs 0.000 description 1
- UREBDLICKHMUKA-DVTGEIKXSA-N betamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-DVTGEIKXSA-N 0.000 description 1
- 125000002618 bicyclic heterocycle group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229960004620 bitolterol Drugs 0.000 description 1
- FZGVEKPRDOIXJY-UHFFFAOYSA-N bitolterol Chemical compound C1=CC(C)=CC=C1C(=O)OC1=CC=C(C(O)CNC(C)(C)C)C=C1OC(=O)C1=CC=C(C)C=C1 FZGVEKPRDOIXJY-UHFFFAOYSA-N 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 229960002802 bromocriptine Drugs 0.000 description 1
- OZVBMTJYIDMWIL-AYFBDAFISA-N bromocriptine Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=C(Br)NC3=C1 OZVBMTJYIDMWIL-AYFBDAFISA-N 0.000 description 1
- FVGVORIVAWDBMI-UHFFFAOYSA-N bromomethane;2,2-diphenylpropanoic acid Chemical compound BrC.C=1C=CC=CC=1C(C(O)=O)(C)C1=CC=CC=C1 FVGVORIVAWDBMI-UHFFFAOYSA-N 0.000 description 1
- OKNSFJXHKUXYLR-UHFFFAOYSA-N bromomethane;2-fluoro-2,2-diphenylacetic acid Chemical compound BrC.C=1C=CC=CC=1C(F)(C(=O)O)C1=CC=CC=C1 OKNSFJXHKUXYLR-UHFFFAOYSA-N 0.000 description 1
- 230000036427 bronchial hyperreactivity Effects 0.000 description 1
- 229950008847 broxaterol Drugs 0.000 description 1
- JBRBWHCVRGURBA-UHFFFAOYSA-N broxaterol Chemical compound CC(C)(C)NCC(O)C1=CC(Br)=NO1 JBRBWHCVRGURBA-UHFFFAOYSA-N 0.000 description 1
- 229960004436 budesonide Drugs 0.000 description 1
- 125000005569 butenylene group Chemical group 0.000 description 1
- 229960004596 cabergoline Drugs 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 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
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 229960001386 carbuterol Drugs 0.000 description 1
- KEMXXQOFIRIICG-UHFFFAOYSA-N carbuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(NC(N)=O)=C1 KEMXXQOFIRIICG-UHFFFAOYSA-N 0.000 description 1
- 210000000748 cardiovascular system Anatomy 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 230000033077 cellular process Effects 0.000 description 1
- 229940081734 cellulose acetate phthalate Drugs 0.000 description 1
- 208000015114 central nervous system disease Diseases 0.000 description 1
- 229960001803 cetirizine Drugs 0.000 description 1
- 229960005395 cetuximab Drugs 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 229960003728 ciclesonide Drugs 0.000 description 1
- 229950001653 cilomilast Drugs 0.000 description 1
- 229960002881 clemastine Drugs 0.000 description 1
- YNNUSGIPVFPVBX-NHCUHLMSSA-N clemastine Chemical compound CN1CCC[C@@H]1CCO[C@@](C)(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 YNNUSGIPVFPVBX-NHCUHLMSSA-N 0.000 description 1
- 229960001117 clenbuterol Drugs 0.000 description 1
- STJMRWALKKWQGH-UHFFFAOYSA-N clenbuterol Chemical compound CC(C)(C)NCC(O)C1=CC(Cl)=C(N)C(Cl)=C1 STJMRWALKKWQGH-UHFFFAOYSA-N 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 229940109275 cyclamate Drugs 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 description 1
- HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical compound O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([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
- 230000003436 cytoskeletal effect Effects 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 229960003957 dexamethasone Drugs 0.000 description 1
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- QPMLSUSACCOBDK-UHFFFAOYSA-N diazepane Chemical compound C1CCNNCC1 QPMLSUSACCOBDK-UHFFFAOYSA-N 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- PBUNVLRHZGSROC-VTIMJTGVSA-N dihydro-alpha-ergocryptine Chemical compound C1=CC([C@H]2C[C@H](CN(C)[C@@H]2C2)C(=O)N[C@]3(C(=O)N4[C@H](C(N5CCC[C@H]5[C@]4(O)O3)=O)CC(C)C)C(C)C)=C3C2=CNC3=C1 PBUNVLRHZGSROC-VTIMJTGVSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- MZDOIJOUFRQXHC-UHFFFAOYSA-N dimenhydrinate Chemical compound O=C1N(C)C(=O)N(C)C2=NC(Cl)=N[C]21.C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 MZDOIJOUFRQXHC-UHFFFAOYSA-N 0.000 description 1
- 229960004993 dimenhydrinate Drugs 0.000 description 1
- 229960001992 dimetindene Drugs 0.000 description 1
- MVMQESMQSYOVGV-UHFFFAOYSA-N dimetindene Chemical compound CN(C)CCC=1CC2=CC=CC=C2C=1C(C)C1=CC=CC=N1 MVMQESMQSYOVGV-UHFFFAOYSA-N 0.000 description 1
- 229960000520 diphenhydramine Drugs 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229960003638 dopamine Drugs 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229960001971 ebastine Drugs 0.000 description 1
- MJJALKDDGIKVBE-UHFFFAOYSA-N ebastine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)CCCN1CCC(OC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 MJJALKDDGIKVBE-UHFFFAOYSA-N 0.000 description 1
- 229960000325 emedastine Drugs 0.000 description 1
- KBUZBQVCBVDWKX-UHFFFAOYSA-N emedastine Chemical compound N=1C2=CC=CC=C2N(CCOCC)C=1N1CCCN(C)CC1 KBUZBQVCBVDWKX-UHFFFAOYSA-N 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- 229960003449 epinastine Drugs 0.000 description 1
- WHWZLSFABNNENI-UHFFFAOYSA-N epinastine Chemical compound C1C2=CC=CC=C2C2CN=C(N)N2C2=CC=CC=C21 WHWZLSFABNNENI-UHFFFAOYSA-N 0.000 description 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- DEFVIWRASFVYLL-UHFFFAOYSA-N ethylene glycol bis(2-aminoethyl)tetraacetic acid Chemical compound OC(=O)CN(CC(O)=O)CCOCCOCCN(CC(O)=O)CC(O)=O DEFVIWRASFVYLL-UHFFFAOYSA-N 0.000 description 1
- 229950006990 etiprednol dicloacetate Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 208000021045 exocrine pancreatic carcinoma Diseases 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 229960001022 fenoterol Drugs 0.000 description 1
- 229960003592 fexofenadine Drugs 0.000 description 1
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 229960000676 flunisolide Drugs 0.000 description 1
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 description 1
- 229960002714 fluticasone Drugs 0.000 description 1
- MGNNYOODZCAHBA-GQKYHHCASA-N fluticasone Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)SCF)(O)[C@@]2(C)C[C@@H]1O MGNNYOODZCAHBA-GQKYHHCASA-N 0.000 description 1
- OATDVDIMNNZTEY-DAXLTYESSA-N flutropium Chemical class C[N@@+]1(CCF)[C@H]2CC[C@@H]1C[C@@H](C2)OC(=O)C(O)(C1=CC=CC=C1)C1=CC=CC=C1 OATDVDIMNNZTEY-DAXLTYESSA-N 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 229960002848 formoterol Drugs 0.000 description 1
- BPZSYCZIITTYBL-UHFFFAOYSA-N formoterol Chemical compound C1=CC(OC)=CC=C1CC(C)NCC(O)C1=CC=C(O)C(NC=O)=C1 BPZSYCZIITTYBL-UHFFFAOYSA-N 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229960005150 glycerol Drugs 0.000 description 1
- 159000000011 group IA salts Chemical class 0.000 description 1
- 208000024963 hair loss Diseases 0.000 description 1
- 230000003676 hair loss Effects 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229940116364 hard fat Drugs 0.000 description 1
- 229960000708 hexoprenaline Drugs 0.000 description 1
- OXLZNBCNGJWPRV-UHFFFAOYSA-N hexoprenaline Chemical compound C=1C=C(O)C(O)=CC=1C(O)CNCCCCCCNCC(O)C1=CC=C(O)C(O)=C1 OXLZNBCNGJWPRV-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- TWTMQRXNAZGSCE-UHFFFAOYSA-N hydron;[6-(methylamino)-1-(2-methylpropanoyloxy)-5,6,7,8-tetrahydronaphthalen-2-yl] 2-methylpropanoate;chloride Chemical compound Cl.C1=CC(OC(=O)C(C)C)=C(OC(=O)C(C)C)C2=C1CC(NC)CC2 TWTMQRXNAZGSCE-UHFFFAOYSA-N 0.000 description 1
- 229950002451 ibuterol Drugs 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000003978 infusion fluid Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical group O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 description 1
- 229960000367 inositol Drugs 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- OEXHQOGQTVQTAT-JRNQLAHRSA-N ipratropium Chemical class O([C@H]1C[C@H]2CC[C@@H](C1)[N@@+]2(C)C(C)C)C(=O)C(CO)C1=CC=CC=C1 OEXHQOGQTVQTAT-JRNQLAHRSA-N 0.000 description 1
- 229960001888 ipratropium Drugs 0.000 description 1
- 208000028867 ischemia Diseases 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 229960001268 isoetarine Drugs 0.000 description 1
- 229960001317 isoprenaline Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- 229960004958 ketotifen Drugs 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 238000000021 kinase assay Methods 0.000 description 1
- 229960001375 lactose Drugs 0.000 description 1
- 229960001120 levocabastine Drugs 0.000 description 1
- ZCGOMHNNNFPNMX-KYTRFIICSA-N levocabastine Chemical compound C1([C@@]2(C(O)=O)CCN(C[C@H]2C)[C@@H]2CC[C@@](CC2)(C#N)C=2C=CC(F)=CC=2)=CC=CC=C1 ZCGOMHNNNFPNMX-KYTRFIICSA-N 0.000 description 1
- 229950008204 levosalbutamol Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229950008462 lirimilast Drugs 0.000 description 1
- 229960003587 lisuride Drugs 0.000 description 1
- 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 1
- 229960003088 loratadine Drugs 0.000 description 1
- JCCNYMKQOSZNPW-UHFFFAOYSA-N loratadine Chemical compound C1CN(C(=O)OCC)CCC1=C1C2=NC=CC=C2CCC2=CC(Cl)=CC=C21 JCCNYMKQOSZNPW-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 201000005296 lung carcinoma Diseases 0.000 description 1
- 229950004407 mabuterol Drugs 0.000 description 1
- JSJCTEKTBOKRST-UHFFFAOYSA-N mabuterol Chemical compound CC(C)(C)NCC(O)C1=CC(Cl)=C(N)C(C(F)(F)F)=C1 JSJCTEKTBOKRST-UHFFFAOYSA-N 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229960001474 meclozine Drugs 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229950001737 meluadrine Drugs 0.000 description 1
- 229910001509 metal bromide Inorganic materials 0.000 description 1
- LMOINURANNBYCM-UHFFFAOYSA-N metaproterenol Chemical compound CC(C)NCC(O)C1=CC(O)=CC(O)=C1 LMOINURANNBYCM-UHFFFAOYSA-N 0.000 description 1
- ZMVAWNCSXGFEDX-UHFFFAOYSA-N methane hydrobromide Chemical compound Br.C[H] ZMVAWNCSXGFEDX-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 229960001144 mizolastine Drugs 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229960001664 mometasone Drugs 0.000 description 1
- QLIIKPVHVRXHRI-CXSFZGCWSA-N mometasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CCl)(O)[C@@]1(C)C[C@@H]2O QLIIKPVHVRXHRI-CXSFZGCWSA-N 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 1
- 229960005127 montelukast Drugs 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- NPGREARFJMFTDF-UHFFFAOYSA-N n-(3,5-dichloro-1-hydroxypyridin-4-ylidene)-8-methoxy-2-(trifluoromethyl)quinoline-5-carboxamide Chemical compound C12=CC=C(C(F)(F)F)N=C2C(OC)=CC=C1C(=O)N=C1C(Cl)=CN(O)C=C1Cl NPGREARFJMFTDF-UHFFFAOYSA-N 0.000 description 1
- VXXUKWLHWFFUNS-UHFFFAOYSA-N n-(7-oxo-5,6-dihydro-4h-1,3-benzothiazol-2-yl)acetamide Chemical compound C1CCC(=O)C2=C1N=C(NC(=O)C)S2 VXXUKWLHWFFUNS-UHFFFAOYSA-N 0.000 description 1
- ZXFOQOWWSCLYBC-UHFFFAOYSA-N n-[2-[5-methyl-4-oxo-2-(7h-purin-6-ylsulfanylmethyl)quinazolin-3-yl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC=C1N1C(=O)C2=C(C)C=CC=C2N=C1CSC1=NC=NC2=C1N=CN2 ZXFOQOWWSCLYBC-UHFFFAOYSA-N 0.000 description 1
- HHRNQOGXBRYCHF-UHFFFAOYSA-N n-[2-hydroxy-5-[1-hydroxy-2-(propan-2-ylamino)ethyl]phenyl]methanesulfonamide Chemical compound CC(C)NCC(O)C1=CC=C(O)C(NS(C)(=O)=O)=C1 HHRNQOGXBRYCHF-UHFFFAOYSA-N 0.000 description 1
- WHFMQMNFGDBTCO-UHFFFAOYSA-N n-[8-(2-fluoro-5-iodophenyl)-4,5-dihydro-[1,3]thiazolo[4,5-h]quinazolin-2-yl]acetamide Chemical compound N1=C2C=3SC(NC(=O)C)=NC=3CCC2=CN=C1C1=CC(I)=CC=C1F WHFMQMNFGDBTCO-UHFFFAOYSA-N 0.000 description 1
- BZYBJPRHOFMEHA-UHFFFAOYSA-N n-[8-(3-chloro-5-iodophenyl)-4,5-dihydro-[1,3]thiazolo[4,5-h]quinazolin-2-yl]acetamide Chemical compound N1=C2C=3SC(NC(=O)C)=NC=3CCC2=CN=C1C1=CC(Cl)=CC(I)=C1 BZYBJPRHOFMEHA-UHFFFAOYSA-N 0.000 description 1
- FIASALYBUKYSNB-UHFFFAOYSA-N n-[8-(3-iodophenyl)-4,5-dihydro-[1,3]thiazolo[4,5-h]quinazolin-2-yl]acetamide Chemical compound N1=C2C=3SC(NC(=O)C)=NC=3CCC2=CN=C1C1=CC=CC(I)=C1 FIASALYBUKYSNB-UHFFFAOYSA-N 0.000 description 1
- KBFZDDQSDVBROH-UHFFFAOYSA-N n-[8-[2-chloro-5-(5-morpholin-4-ylpent-1-ynyl)phenyl]-4,5-dihydro-[1,3]thiazolo[4,5-h]quinazolin-2-yl]acetamide Chemical compound N1=C2C=3SC(NC(=O)C)=NC=3CCC2=CN=C1C(C(=CC=1)Cl)=CC=1C#CCCCN1CCOCC1 KBFZDDQSDVBROH-UHFFFAOYSA-N 0.000 description 1
- OEYXZMSXSCVBGK-UHFFFAOYSA-N n-[8-[2-chloro-5-[3-(cyclopentylamino)prop-1-ynyl]phenyl]-4,5-dihydro-[1,3]thiazolo[4,5-h]quinazolin-2-yl]acetamide Chemical compound N1=C2C=3SC(NC(=O)C)=NC=3CCC2=CN=C1C(C(=CC=1)Cl)=CC=1C#CCNC1CCCC1 OEYXZMSXSCVBGK-UHFFFAOYSA-N 0.000 description 1
- NDPYHSPOIIEDAI-UHFFFAOYSA-N n-[8-[2-chloro-5-[3-(methylcarbamoylamino)prop-1-ynyl]phenyl]-4,5-dihydro-[1,3]thiazolo[4,5-h]quinazolin-2-yl]acetamide Chemical compound CNC(=O)NCC#CC1=CC=C(Cl)C(C=2N=C3C=4SC(NC(C)=O)=NC=4CCC3=CN=2)=C1 NDPYHSPOIIEDAI-UHFFFAOYSA-N 0.000 description 1
- YFSWGTUUQBVGMP-UHFFFAOYSA-N n-[8-[5-(3-aminoprop-1-ynyl)-2-chlorophenyl]-4,5-dihydro-[1,3]thiazolo[4,5-h]quinazolin-2-yl]acetamide Chemical compound N1=C2C=3SC(NC(=O)C)=NC=3CCC2=CN=C1C1=CC(C#CCN)=CC=C1Cl YFSWGTUUQBVGMP-UHFFFAOYSA-N 0.000 description 1
- QSYCBPWAOPTASM-UHFFFAOYSA-N n-[8-[5-[3-[acetyl(methyl)amino]prop-1-ynyl]-2-chlorophenyl]-4,5-dihydro-[1,3]thiazolo[4,5-h]quinazolin-2-yl]acetamide Chemical compound CC(=O)N(C)CC#CC1=CC=C(Cl)C(C=2N=C3C=4SC(NC(C)=O)=NC=4CCC3=CN=2)=C1 QSYCBPWAOPTASM-UHFFFAOYSA-N 0.000 description 1
- MKMFOYQRIMLCSV-UHFFFAOYSA-N n-[[3-(2-chlorophenyl)-5-fluoro-4-oxoquinazolin-2-yl]methyl]-2-(7h-purin-6-ylsulfanyl)acetamide Chemical compound O=C1C=2C(F)=CC=CC=2N=C(CNC(=O)CSC=2C=3N=CNC=3N=CN=2)N1C1=CC=CC=C1Cl MKMFOYQRIMLCSV-UHFFFAOYSA-N 0.000 description 1
- ZAAHIXQDGNSNAD-UHFFFAOYSA-N n-but-3-ynyl-n-methylacetamide Chemical compound CC(=O)N(C)CCC#C ZAAHIXQDGNSNAD-UHFFFAOYSA-N 0.000 description 1
- 125000004370 n-butenyl group Chemical group [H]\C([H])=C(/[H])C([H])([H])C([H])([H])* 0.000 description 1
- HQFYIDOMCULPIW-UHFFFAOYSA-N n-methylprop-2-yn-1-amine Chemical compound CNCC#C HQFYIDOMCULPIW-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 230000000414 obstructive effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229940100692 oral suspension Drugs 0.000 description 1
- 229960002657 orciprenaline Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000002611 ovarian Effects 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 208000008443 pancreatic carcinoma Diseases 0.000 description 1
- 229960001972 panitumumab Drugs 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- CRWVOXFUXPYTRK-UHFFFAOYSA-N pent-4-yn-1-ol Chemical compound OCCCC#C CRWVOXFUXPYTRK-UHFFFAOYSA-N 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 229960004851 pergolide Drugs 0.000 description 1
- YEHCICAEULNIGD-MZMPZRCHSA-N pergolide Chemical compound C1=CC([C@H]2C[C@@H](CSC)CN([C@@H]2C2)CCC)=C3C2=CNC3=C1 YEHCICAEULNIGD-MZMPZRCHSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000002831 pharmacologic agent Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 1
- 150000008104 phosphatidylethanolamines Chemical class 0.000 description 1
- 150000003906 phosphoinositides Chemical group 0.000 description 1
- 102000020233 phosphotransferase Human genes 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- XBXHCBLBYQEYTI-UHFFFAOYSA-N piperidin-4-ylmethanol Chemical compound OCC1CCNCC1 XBXHCBLBYQEYTI-UHFFFAOYSA-N 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229960005414 pirbuterol Drugs 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229960003089 pramipexole Drugs 0.000 description 1
- FASDKYOPVNHBLU-ZETCQYMHSA-N pramipexole Chemical compound C1[C@@H](NCCC)CCC2=C1SC(N)=N2 FASDKYOPVNHBLU-ZETCQYMHSA-N 0.000 description 1
- UAJUXJSXCLUTNU-UHFFFAOYSA-N pranlukast Chemical compound C=1C=C(OCCCCC=2C=CC=CC=2)C=CC=1C(=O)NC(C=1)=CC=C(C(C=2)=O)C=1OC=2C=1N=NNN=1 UAJUXJSXCLUTNU-UHFFFAOYSA-N 0.000 description 1
- 229960004583 pranlukast Drugs 0.000 description 1
- 229960005205 prednisolone Drugs 0.000 description 1
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 1
- 229960004618 prednisone Drugs 0.000 description 1
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 229960002288 procaterol Drugs 0.000 description 1
- FKNXQNWAXFXVNW-BLLLJJGKSA-N procaterol Chemical compound N1C(=O)C=CC2=C1C(O)=CC=C2[C@@H](O)[C@@H](NC(C)C)CC FKNXQNWAXFXVNW-BLLLJJGKSA-N 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 229960003910 promethazine Drugs 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000003909 protein kinase inhibitor Substances 0.000 description 1
- 208000005069 pulmonary fibrosis Diseases 0.000 description 1
- 229950010090 pumafentrine Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000001698 pyrogenic effect Effects 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 1
- MIXMJCQRHVAJIO-TZHJZOAOSA-N qk4dys664x Chemical compound O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O MIXMJCQRHVAJIO-TZHJZOAOSA-N 0.000 description 1
- 239000011535 reaction buffer Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004314 regulation of intracellular transport Effects 0.000 description 1
- 229960002720 reproterol Drugs 0.000 description 1
- WVLAAKXASPCBGT-UHFFFAOYSA-N reproterol Chemical compound C1=2C(=O)N(C)C(=O)N(C)C=2N=CN1CCCNCC(O)C1=CC(O)=CC(O)=C1 WVLAAKXASPCBGT-UHFFFAOYSA-N 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- 229960001457 rimiterol Drugs 0.000 description 1
- IYMMESGOJVNCKV-SKDRFNHKSA-N rimiterol Chemical compound C([C@@H]1[C@@H](O)C=2C=C(O)C(O)=CC=2)CCCN1 IYMMESGOJVNCKV-SKDRFNHKSA-N 0.000 description 1
- IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
- IXTCZMJQGGONPY-XJAYAHQCSA-N rofleponide Chemical compound C1([C@@H](F)C2)=CC(=O)CC[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@H]3O[C@@H](CCC)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O IXTCZMJQGGONPY-XJAYAHQCSA-N 0.000 description 1
- 229950004432 rofleponide Drugs 0.000 description 1
- MNDBXUUTURYVHR-UHFFFAOYSA-N roflumilast Chemical compound FC(F)OC1=CC=C(C(=O)NC=2C(=CN=CC=2Cl)Cl)C=C1OCC1CC1 MNDBXUUTURYVHR-UHFFFAOYSA-N 0.000 description 1
- 229960002586 roflumilast Drugs 0.000 description 1
- 229960001879 ropinirole Drugs 0.000 description 1
- UHSKFQJFRQCDBE-UHFFFAOYSA-N ropinirole Chemical compound CCCN(CCC)CCC1=CC=CC2=C1CC(=O)N2 UHSKFQJFRQCDBE-UHFFFAOYSA-N 0.000 description 1
- BKTTWZADZNUOBW-UHFFFAOYSA-N roxindole Chemical compound C=12[CH]C(O)=CC=C2N=CC=1CCCCN(CC=1)CCC=1C1=CC=CC=C1 BKTTWZADZNUOBW-UHFFFAOYSA-N 0.000 description 1
- 229950000366 roxindole Drugs 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 229960002052 salbutamol Drugs 0.000 description 1
- 229950001879 salmefamol Drugs 0.000 description 1
- 229960004017 salmeterol Drugs 0.000 description 1
- FIMXSEMBHGTNKT-RZVDLVGDSA-N scopine Chemical compound C([C@@H]1N2C)[C@H](O)C[C@@H]2[C@@H]2[C@H]1O2 FIMXSEMBHGTNKT-RZVDLVGDSA-N 0.000 description 1
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
- 230000036303 septic shock Effects 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229940080313 sodium starch Drugs 0.000 description 1
- HOAUAOBUGFYWMK-UHFFFAOYSA-M sodium;propanoate;hydrate Chemical compound O.[Na+].CCC([O-])=O HOAUAOBUGFYWMK-UHFFFAOYSA-M 0.000 description 1
- 229950010289 soterenol Drugs 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 208000023516 stroke disease Diseases 0.000 description 1
- 238000007920 subcutaneous administration 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
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 229950007862 sulfonterol Drugs 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 229960004558 terguride Drugs 0.000 description 1
- YDBPZCVWPFMBDH-MRVPVSSYSA-N tert-butyl (2r)-2-formylpyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC[C@@H]1C=O YDBPZCVWPFMBDH-MRVPVSSYSA-N 0.000 description 1
- YDBPZCVWPFMBDH-QMMMGPOBSA-N tert-butyl (2s)-2-formylpyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC[C@H]1C=O YDBPZCVWPFMBDH-QMMMGPOBSA-N 0.000 description 1
- CTEDVGRUGMPBHE-UHFFFAOYSA-N tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(CO)CC1 CTEDVGRUGMPBHE-UHFFFAOYSA-N 0.000 description 1
- INUWDZDWSJJFSQ-UHFFFAOYSA-N tert-butyl 4-ethynylpiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(C#C)CC1 INUWDZDWSJJFSQ-UHFFFAOYSA-N 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- HNDGEYCCZGRMTN-UHFFFAOYSA-N thieno[3,2-f:4,5-f]bis[1]benzothiophene Chemical compound S1C2=CC=3SC=CC=3C=C2C2=C1C=C(SC=C1)C1=C2 HNDGEYCCZGRMTN-UHFFFAOYSA-N 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- LERNTVKEWCAPOY-DZZGSBJMSA-N tiotropium Chemical class O([C@H]1C[C@@H]2[N+]([C@H](C1)[C@@H]1[C@H]2O1)(C)C)C(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 LERNTVKEWCAPOY-DZZGSBJMSA-N 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- 229950003899 tofimilast Drugs 0.000 description 1
- OOGJQPCLVADCPB-HXUWFJFHSA-N tolterodine Chemical compound C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(C)C=2)O)=CC=CC=C1 OOGJQPCLVADCPB-HXUWFJFHSA-N 0.000 description 1
- 229960004045 tolterodine Drugs 0.000 description 1
- 238000012876 topography Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229960000575 trastuzumab Drugs 0.000 description 1
- 229960005294 triamcinolone Drugs 0.000 description 1
- GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 description 1
- 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
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
- OYYDSUSKLWTMMQ-JKHIJQBDSA-N trospium Chemical class [N+]12([C@@H]3CC[C@H]2C[C@H](C3)OC(=O)C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CCCC1 OYYDSUSKLWTMMQ-JKHIJQBDSA-N 0.000 description 1
- BDIAUFOIMFAIPU-UHFFFAOYSA-N valepotriate Natural products CC(C)CC(=O)OC1C=C(C(=COC2OC(=O)CC(C)C)COC(C)=O)C2C11CO1 BDIAUFOIMFAIPU-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229960004764 zafirlukast Drugs 0.000 description 1
- XJBCFFLVLOPYBV-UHFFFAOYSA-N zinterol Chemical compound C=1C=C(O)C(NS(C)(=O)=O)=CC=1C(O)CNC(C)(C)CC1=CC=CC=C1 XJBCFFLVLOPYBV-UHFFFAOYSA-N 0.000 description 1
- 229950004209 zinterol Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/429—Thiazoles condensed with heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/14—Antitussive agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/16—Central respiratory analeptics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/08—Antiseborrheics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/10—Anti-acne agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/14—Drugs for dermatological disorders for baldness or alopecia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/14—Decongestants or antiallergics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Dermatology (AREA)
- Ophthalmology & Optometry (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Otolaryngology (AREA)
- Neurology (AREA)
- Gastroenterology & Hepatology (AREA)
- Biomedical Technology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Neurosurgery (AREA)
- Urology & Nephrology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP06112300 | 2006-04-06 | ||
| EP06112300 | 2006-04-06 | ||
| PCT/EP2007/052912 WO2007115929A1 (de) | 2006-04-06 | 2007-03-27 | Thiazolyl-dihydro-quinazoline |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2425051T3 true ES2425051T3 (es) | 2013-10-11 |
Family
ID=36790884
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES07727385T Active ES2425051T3 (es) | 2006-04-06 | 2007-03-27 | Tiazolil-dihidro-quinazolinas |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US7691868B2 (enExample) |
| EP (1) | EP2018385B1 (enExample) |
| JP (1) | JP5303450B2 (enExample) |
| KR (1) | KR20090029181A (enExample) |
| CN (2) | CN103172589A (enExample) |
| AR (1) | AR060269A1 (enExample) |
| AU (1) | AU2007236043B2 (enExample) |
| BR (1) | BRPI0710575A2 (enExample) |
| CA (1) | CA2647056A1 (enExample) |
| DK (1) | DK2018385T3 (enExample) |
| ES (1) | ES2425051T3 (enExample) |
| IL (1) | IL194490A0 (enExample) |
| MX (1) | MX2008011957A (enExample) |
| NZ (1) | NZ572508A (enExample) |
| RU (1) | RU2008143546A (enExample) |
| TW (1) | TW200804402A (enExample) |
| WO (1) | WO2007115929A1 (enExample) |
| ZA (1) | ZA200807349B (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070238746A1 (en) * | 2006-04-06 | 2007-10-11 | Trixi Brandl | Thiazolyl-dihydro-chinazoline |
| US7691868B2 (en) | 2006-04-06 | 2010-04-06 | Boehringer Ingelheim International Gmbh | Thiazolyl-dihydro-quinazoline |
| US20070259855A1 (en) * | 2006-04-06 | 2007-11-08 | Udo Maier | Thiazolyl-dihydro-indazole |
| JPWO2010024258A1 (ja) * | 2008-08-29 | 2012-01-26 | 塩野義製薬株式会社 | Ｐｉ３ｋ阻害活性を有する縮環アゾール誘導体 |
| US20120071475A1 (en) * | 2009-04-27 | 2012-03-22 | Shionogi & Co., Ltd. | Urea derivatives having pi3k-inhibiting activity |
| EA201200087A1 (ru) * | 2009-07-02 | 2012-07-30 | Новартис Аг | 2-карбоксамиды циклоаминомочевин, которые являются ингибиторами pi3k |
| US11633399B2 (en) | 2018-12-25 | 2023-04-25 | Sol-Gel Technologies Ltd. | Treatment of skin disorders with compositions comprising an EGFR inhibitor |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US244104A (en) * | 1881-07-12 | andrews | ||
| US259855A (en) * | 1882-06-20 | Fbank s | ||
| US238718A (en) * | 1881-03-08 | Efeico eosenzi | ||
| US238730A (en) * | 1881-03-08 | Wagon-brake | ||
| US4380640A (en) * | 1980-01-21 | 1983-04-19 | Ciba-Geigy Corporation | Novel benzthiazolylurea derivatives, compositions containing them and their use as herbicides |
| CN1422262A (zh) | 2000-02-07 | 2003-06-04 | 艾博特股份有限两合公司 | 2－苯并噻唑基脲衍生物及其作为蛋白激酶抑制剂的应用 |
| US20040009613A1 (en) * | 2001-02-16 | 2004-01-15 | Ming-Ming Zhou | Methods of identifying modulators of bromodomains |
| US6608053B2 (en) * | 2000-04-27 | 2003-08-19 | Yamanouchi Pharmaceutical Co., Ltd. | Fused heteroaryl derivatives |
| MY156407A (en) | 2002-02-28 | 2016-02-26 | Novartis Ag | 5-phenylthiazole derivatives and use as p13 kinase inhibitors |
| BR0312650A (pt) | 2002-07-10 | 2005-05-03 | Applied Research Systems | Derivados de benzeno fundido azolidinona-vinila |
| HRP20131159B1 (hr) | 2002-09-30 | 2019-11-01 | Bayer Ip Gmbh | Taljeni azol-pirimidin derivati |
| MXPA05005585A (es) | 2002-12-06 | 2005-07-27 | Warner Lambert Co | Benzoxazin-3-onas y derivados de las mismas como agentes terapeuticos. |
| JP2006512357A (ja) | 2002-12-20 | 2006-04-13 | ワーナー−ランバート・カンパニー、リミテッド、ライアビリティ、カンパニー | Ｐｉ３ｋの阻害剤としてのベンゾキサジンおよびその誘導体 |
| CA2528938A1 (en) | 2003-06-13 | 2005-02-24 | Zentaris Gmbh | Compounds having inhibitive activity of phosphatidylinositol 3-kinase and methods of use thereof |
| GB0315966D0 (en) | 2003-07-08 | 2003-08-13 | Cyclacel Ltd | Compounds |
| CN1897950A (zh) | 2003-10-14 | 2007-01-17 | 惠氏公司 | 稠合芳基和杂芳基衍生物及其使用方法 |
| RU2403258C2 (ru) * | 2004-10-07 | 2010-11-10 | Бёрингер Ингельхайм Интернациональ Гмбх | Тиазолилдигидроиндазолы |
| UY29149A1 (es) | 2004-10-07 | 2006-05-31 | Boehringer Ingelheim Int | Tiazolil-dihidro-indazoles |
| US20070238746A1 (en) * | 2006-04-06 | 2007-10-11 | Trixi Brandl | Thiazolyl-dihydro-chinazoline |
| US7517995B2 (en) | 2006-04-06 | 2009-04-14 | Boehringer Ingelheim International Gmbh | Thiazolyl-dihydro-cyclopentapyrazole |
| US20070259855A1 (en) | 2006-04-06 | 2007-11-08 | Udo Maier | Thiazolyl-dihydro-indazole |
| US20070238718A1 (en) | 2006-04-06 | 2007-10-11 | Matthias Grauert | Thiazolyl-dihydro-indazole |
| US7691868B2 (en) | 2006-04-06 | 2010-04-06 | Boehringer Ingelheim International Gmbh | Thiazolyl-dihydro-quinazoline |
-
2007
- 2007-03-23 US US11/690,362 patent/US7691868B2/en active Active
- 2007-03-27 CN CN201310049412XA patent/CN103172589A/zh active Pending
- 2007-03-27 RU RU2008143546/04A patent/RU2008143546A/ru not_active Application Discontinuation
- 2007-03-27 MX MX2008011957A patent/MX2008011957A/es active IP Right Grant
- 2007-03-27 JP JP2009503532A patent/JP5303450B2/ja not_active Expired - Fee Related
- 2007-03-27 CN CN2007800207880A patent/CN101460505B/zh not_active Expired - Fee Related
- 2007-03-27 NZ NZ572508A patent/NZ572508A/en not_active IP Right Cessation
- 2007-03-27 CA CA002647056A patent/CA2647056A1/en not_active Abandoned
- 2007-03-27 ES ES07727385T patent/ES2425051T3/es active Active
- 2007-03-27 BR BRPI0710575-4A patent/BRPI0710575A2/pt not_active IP Right Cessation
- 2007-03-27 EP EP07727385.2A patent/EP2018385B1/de not_active Not-in-force
- 2007-03-27 WO PCT/EP2007/052912 patent/WO2007115929A1/de not_active Ceased
- 2007-03-27 KR KR1020087027076A patent/KR20090029181A/ko not_active Ceased
- 2007-03-27 DK DK07727385.2T patent/DK2018385T3/da active
- 2007-03-27 AU AU2007236043A patent/AU2007236043B2/en not_active Ceased
- 2007-04-03 AR ARP070101387A patent/AR060269A1/es unknown
- 2007-04-04 TW TW096111946A patent/TW200804402A/zh unknown
-
2008
- 2008-08-26 ZA ZA200807349A patent/ZA200807349B/xx unknown
- 2008-10-02 IL IL194490A patent/IL194490A0/en unknown
-
2010
- 2010-02-17 US US12/706,936 patent/US8334378B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN103172589A (zh) | 2013-06-26 |
| TW200804402A (en) | 2008-01-16 |
| RU2008143546A (ru) | 2010-06-27 |
| AR060269A1 (es) | 2008-06-04 |
| CN101460505A (zh) | 2009-06-17 |
| CN101460505B (zh) | 2013-03-20 |
| AU2007236043B2 (en) | 2012-09-13 |
| ZA200807349B (en) | 2009-07-29 |
| US7691868B2 (en) | 2010-04-06 |
| JP2009532413A (ja) | 2009-09-10 |
| NZ572508A (en) | 2011-11-25 |
| BRPI0710575A2 (pt) | 2012-06-19 |
| WO2007115929A1 (de) | 2007-10-18 |
| JP5303450B2 (ja) | 2013-10-02 |
| WO2007115929A8 (de) | 2008-06-19 |
| KR20090029181A (ko) | 2009-03-20 |
| CA2647056A1 (en) | 2007-10-18 |
| US8334378B2 (en) | 2012-12-18 |
| EP2018385B1 (de) | 2013-05-15 |
| US20100145041A1 (en) | 2010-06-10 |
| AU2007236043A1 (en) | 2007-10-18 |
| US20070244104A1 (en) | 2007-10-18 |
| DK2018385T3 (da) | 2013-08-26 |
| MX2008011957A (es) | 2008-10-01 |
| EP2018385A1 (de) | 2009-01-28 |
| IL194490A0 (en) | 2009-08-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5237262B2 (ja) | チアゾリル−ジヒドロキナゾリン | |
| CN101460167A (zh) | 用作pi3-激酶抑制剂的噻唑基-二氢-环戊二烯并吡唑 | |
| EP1802636A1 (de) | Pi3-kinasen | |
| BRPI0709743A2 (pt) | tiazolil-diidro-indazol | |
| ES2425051T3 (es) | Tiazolil-dihidro-quinazolinas | |
| BRPI0710847A2 (pt) | compostos de tiazolil-dihidro-indazóis, uso dos mesmos,formulação farmacêutica e combinações de medicamentos | |
| NZ563448A (en) | Benzofuranone derivatives for treating inflammatory diseases | |
| HK1115018A (en) | Dihydrothienopyrimidines for the treatment of inflammatory diseases | |
| DE102005005813A1 (de) | PI3-Kinasen |