TWI313269B - Pyrazole compounds useful as protein kinase inhibitors - Google Patents
Pyrazole compounds useful as protein kinase inhibitors Download PDFInfo
- Publication number
- TWI313269B TWI313269B TW095139649A TW95139649A TWI313269B TW I313269 B TWI313269 B TW I313269B TW 095139649 A TW095139649 A TW 095139649A TW 95139649 A TW95139649 A TW 95139649A TW I313269 B TWI313269 B TW I313269B
- Authority
- TW
- Taiwan
- Prior art keywords
- ring
- group
- aliphatic
- amine
- phenyl
- Prior art date
Links
- 239000003909 protein kinase inhibitor Substances 0.000 title description 7
- 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 title description 5
- 150000003217 pyrazoles Chemical class 0.000 title 1
- 125000001931 aliphatic group Chemical group 0.000 claims description 349
- -1 acetamino group Chemical group 0.000 claims description 274
- 229910052739 hydrogen Inorganic materials 0.000 claims description 257
- 150000001875 compounds Chemical class 0.000 claims description 255
- 239000001257 hydrogen Substances 0.000 claims description 254
- 238000000034 method Methods 0.000 claims description 252
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 229
- 229910052757 nitrogen Inorganic materials 0.000 claims description 186
- 125000000217 alkyl group Chemical group 0.000 claims description 162
- 125000001424 substituent group Chemical group 0.000 claims description 147
- 125000001072 heteroaryl group Chemical group 0.000 claims description 146
- 125000003118 aryl group Chemical group 0.000 claims description 123
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 120
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 118
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 116
- 201000010099 disease Diseases 0.000 claims description 115
- 125000002619 bicyclic group Chemical group 0.000 claims description 101
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 87
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 79
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 79
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 73
- 108010014905 Glycogen Synthase Kinase 3 Proteins 0.000 claims description 70
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 70
- 230000002401 inhibitory effect Effects 0.000 claims description 69
- 125000005842 heteroatom Chemical group 0.000 claims description 68
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 67
- 229910052760 oxygen Inorganic materials 0.000 claims description 66
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 65
- 239000001301 oxygen Substances 0.000 claims description 65
- 229910052717 sulfur Inorganic materials 0.000 claims description 64
- 239000008194 pharmaceutical composition Substances 0.000 claims description 61
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 59
- 125000000623 heterocyclic group Chemical group 0.000 claims description 58
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 54
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 54
- 239000011593 sulfur Substances 0.000 claims description 53
- 108090000461 Aurora Kinase A Proteins 0.000 claims description 47
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 47
- 230000000694 effects Effects 0.000 claims description 46
- 125000005843 halogen group Chemical group 0.000 claims description 46
- 102100032311 Aurora kinase A Human genes 0.000 claims description 45
- 229910052799 carbon Inorganic materials 0.000 claims description 45
- 125000004429 atom Chemical group 0.000 claims description 43
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 41
- 125000002950 monocyclic group Chemical group 0.000 claims description 41
- 125000005605 benzo group Chemical group 0.000 claims description 37
- 239000012472 biological sample Substances 0.000 claims description 35
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 35
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 33
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 31
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 30
- 230000001404 mediated effect Effects 0.000 claims description 30
- 125000003282 alkyl amino group Chemical group 0.000 claims description 27
- 101150090422 gsk-3 gene Proteins 0.000 claims description 24
- 239000003937 drug carrier Substances 0.000 claims description 23
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 22
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 21
- 206010012601 diabetes mellitus Diseases 0.000 claims description 20
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 20
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 19
- 230000015572 biosynthetic process Effects 0.000 claims description 18
- 239000003814 drug Substances 0.000 claims description 18
- 125000002837 carbocyclic group Chemical group 0.000 claims description 17
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- 125000004984 dialkylaminoalkoxy group Chemical group 0.000 claims description 15
- 201000000980 schizophrenia Diseases 0.000 claims description 15
- 238000003786 synthesis reaction Methods 0.000 claims description 15
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 14
- 239000008103 glucose Substances 0.000 claims description 14
- 108090000623 proteins and genes Proteins 0.000 claims description 13
- 230000001225 therapeutic effect Effects 0.000 claims description 13
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 12
- 102000004169 proteins and genes Human genes 0.000 claims description 12
- 150000001412 amines Chemical group 0.000 claims description 11
- 230000002440 hepatic effect Effects 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 125000003277 amino group Chemical group 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 208000024827 Alzheimer disease Diseases 0.000 claims description 8
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 8
- 125000003418 alkyl amino alkoxy group Chemical group 0.000 claims description 8
- 239000007789 gas Substances 0.000 claims description 8
- 150000002923 oximes Chemical class 0.000 claims description 8
- 101150001535 SRC gene Proteins 0.000 claims description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
- 125000005577 anthracene group Chemical group 0.000 claims description 6
- 206010009944 Colon cancer Diseases 0.000 claims description 5
- 229940079593 drug Drugs 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000005265 dialkylamine group Chemical group 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 201000004384 Alopecia Diseases 0.000 claims description 3
- 206010007572 Cardiac hypertrophy Diseases 0.000 claims description 3
- 208000006029 Cardiomegaly Diseases 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 231100000360 alopecia Toxicity 0.000 claims description 3
- 208000029742 colonic neoplasm Diseases 0.000 claims description 3
- 201000006417 multiple sclerosis Diseases 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 238000012360 testing method Methods 0.000 claims description 3
- 208000030507 AIDS Diseases 0.000 claims description 2
- 206010006187 Breast cancer Diseases 0.000 claims description 2
- 208000026310 Breast neoplasm Diseases 0.000 claims description 2
- 208000023105 Huntington disease Diseases 0.000 claims description 2
- 206010033128 Ovarian cancer Diseases 0.000 claims description 2
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 2
- 208000018737 Parkinson disease Diseases 0.000 claims description 2
- 208000005718 Stomach Neoplasms Diseases 0.000 claims description 2
- 206010017758 gastric cancer Diseases 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 230000010410 reperfusion Effects 0.000 claims description 2
- 201000011549 stomach cancer Diseases 0.000 claims description 2
- 125000006413 ring segment Chemical group 0.000 claims 4
- 125000000468 ketone group Chemical group 0.000 claims 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 claims 1
- TXWDVWSJMDFNQY-UHFFFAOYSA-N 5-cyclopropyl-1h-pyrazole Chemical compound C1CC1C1=CC=NN1 TXWDVWSJMDFNQY-UHFFFAOYSA-N 0.000 claims 1
- RMCHMFQKTDFRGS-UHFFFAOYSA-N C1(CC1)C=1C=C(NN1)NC1=NC(=NC=C1C)SC=1NC2=CC=CC=C2C1 Chemical compound C1(CC1)C=1C=C(NN1)NC1=NC(=NC=C1C)SC=1NC2=CC=CC=C2C1 RMCHMFQKTDFRGS-UHFFFAOYSA-N 0.000 claims 1
- 206010012289 Dementia Diseases 0.000 claims 1
- 102000002254 Glycogen Synthase Kinase 3 Human genes 0.000 claims 1
- 229930194542 Keto Natural products 0.000 claims 1
- 206010039424 Salivary hypersecretion Diseases 0.000 claims 1
- 208000034189 Sclerosis Diseases 0.000 claims 1
- 239000012141 concentrate Substances 0.000 claims 1
- 125000005567 fluorenylene group Chemical group 0.000 claims 1
- 239000004615 ingredient Substances 0.000 claims 1
- CWGCAXSXZAOMRF-UHFFFAOYSA-N n-[4-[4-(2-methylphenyl)-6-[(5-methyl-1h-pyrazol-3-yl)amino]pyrimidin-2-yl]sulfanylphenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1SC1=NC(NC=2NN=C(C)C=2)=CC(C=2C(=CC=CC=2)C)=N1 CWGCAXSXZAOMRF-UHFFFAOYSA-N 0.000 claims 1
- BGNRYQCGVJJPRI-UHFFFAOYSA-N n-[4-[4-[(5-methyl-1h-pyrazol-3-yl)amino]pyrimidin-2-yl]sulfanylphenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1SC1=NC=CC(NC=2NN=C(C)C=2)=N1 BGNRYQCGVJJPRI-UHFFFAOYSA-N 0.000 claims 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 claims 1
- 230000001737 promoting effect Effects 0.000 claims 1
- 208000026451 salivation Diseases 0.000 claims 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 226
- 239000007787 solid Substances 0.000 description 162
- 125000004093 cyano group Chemical group *C#N 0.000 description 111
- 150000002431 hydrogen Chemical class 0.000 description 96
- 239000002585 base Substances 0.000 description 93
- 239000000126 substance Substances 0.000 description 78
- 239000000203 mixture Substances 0.000 description 75
- 238000005481 NMR spectroscopy Methods 0.000 description 74
- 230000004927 fusion Effects 0.000 description 73
- 102000001267 GSK3 Human genes 0.000 description 69
- 125000001475 halogen functional group Chemical group 0.000 description 60
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 47
- 239000003112 inhibitor Substances 0.000 description 47
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 44
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 40
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 29
- 239000000243 solution Substances 0.000 description 29
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- 150000002829 nitrogen Chemical class 0.000 description 26
- 238000002560 therapeutic procedure Methods 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 239000000460 chlorine Substances 0.000 description 23
- 125000003226 pyrazolyl group Chemical group 0.000 description 23
- 125000000714 pyrimidinyl group Chemical group 0.000 description 23
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 230000005764 inhibitory process Effects 0.000 description 20
- 229940002612 prodrug Drugs 0.000 description 19
- 239000000651 prodrug Substances 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 206010028980 Neoplasm Diseases 0.000 description 18
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 18
- 125000004008 6 membered carbocyclic group Chemical group 0.000 description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 17
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 16
- 235000019439 ethyl acetate Nutrition 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 15
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 15
- 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 15
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 15
- 210000004369 blood Anatomy 0.000 description 14
- 239000008280 blood Substances 0.000 description 14
- 201000011510 cancer Diseases 0.000 description 14
- 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 description 14
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 14
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 14
- 125000004076 pyridyl group Chemical group 0.000 description 14
- 229920006395 saturated elastomer Polymers 0.000 description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 14
- 208000031124 Dementia Alzheimer type Diseases 0.000 description 13
- 125000003545 alkoxy group Chemical group 0.000 description 13
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 13
- 125000006165 cyclic alkyl group Chemical group 0.000 description 13
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 13
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 12
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 125000002971 oxazolyl group Chemical group 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- 102000001253 Protein Kinase Human genes 0.000 description 11
- 210000004027 cell Anatomy 0.000 description 11
- 238000001914 filtration Methods 0.000 description 11
- 125000002757 morpholinyl group Chemical group 0.000 description 11
- 108060006633 protein kinase Proteins 0.000 description 11
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 11
- 102000013498 tau Proteins Human genes 0.000 description 11
- 108010026424 tau Proteins Proteins 0.000 description 11
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 10
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 10
- 125000006355 carbonyl methylene group Chemical group [H]C([H])([*:2])C([*:1])=O 0.000 description 10
- 125000001309 chloro group Chemical group Cl* 0.000 description 10
- 230000002708 enhancing effect Effects 0.000 description 10
- 238000003818 flash chromatography Methods 0.000 description 10
- 230000026731 phosphorylation Effects 0.000 description 10
- 238000006366 phosphorylation reaction Methods 0.000 description 10
- 102100024193 Mitogen-activated protein kinase 1 Human genes 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
- 108700015928 Mitogen-activated protein kinase 13 Proteins 0.000 description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- 108091008611 Protein Kinase B Proteins 0.000 description 8
- 235000019197 fats Nutrition 0.000 description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 229940124597 therapeutic agent Drugs 0.000 description 8
- 229920002527 Glycogen Polymers 0.000 description 7
- 102100033810 RAC-alpha serine/threonine-protein kinase Human genes 0.000 description 7
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 7
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 7
- 150000001335 aliphatic alkanes Chemical class 0.000 description 7
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 7
- 229940096919 glycogen Drugs 0.000 description 7
- 125000000687 hydroquinonyl group Chemical group C1(O)=C(C=C(O)C=C1)* 0.000 description 7
- 125000005647 linker group Chemical group 0.000 description 7
- 125000006525 methoxy ethyl amino group Chemical group [H]N(*)C([H])([H])C([H])([H])OC([H])([H])[H] 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 6
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- 101100439046 Caenorhabditis elegans cdk-2 gene Proteins 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 102000004877 Insulin Human genes 0.000 description 6
- 108090001061 Insulin Proteins 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- 206010036790 Productive cough Diseases 0.000 description 6
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 6
- 229940125396 insulin Drugs 0.000 description 6
- 230000002265 prevention Effects 0.000 description 6
- 229910052707 ruthenium Inorganic materials 0.000 description 6
- 210000003802 sputum Anatomy 0.000 description 6
- 208000024794 sputum Diseases 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 5
- QCYOIFVBYZNUNW-UHFFFAOYSA-N 2-(dimethylazaniumyl)propanoate Chemical compound CN(C)C(C)C(O)=O QCYOIFVBYZNUNW-UHFFFAOYSA-N 0.000 description 5
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 5
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 5
- 108060000903 Beta-catenin Proteins 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-O Piperidinium(1+) Chemical compound C1CC[NH2+]CC1 NQRYJNQNLNOLGT-UHFFFAOYSA-O 0.000 description 5
- 125000006524 alkoxy alkyl amino group Chemical group 0.000 description 5
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 5
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 5
- 125000001188 haloalkyl group Chemical group 0.000 description 5
- 230000006951 hyperphosphorylation Effects 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 5
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical group [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 208000023275 Autoimmune disease Diseases 0.000 description 4
- 102000015735 Beta-catenin Human genes 0.000 description 4
- 102000038624 GSKs Human genes 0.000 description 4
- 102000014150 Interferons Human genes 0.000 description 4
- 108010050904 Interferons Proteins 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- 108091000080 Phosphotransferase Proteins 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 230000002159 abnormal effect Effects 0.000 description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 4
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 4
- 235000019253 formic acid Nutrition 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 4
- 230000020477 pH reduction Effects 0.000 description 4
- 230000037361 pathway Effects 0.000 description 4
- 102000020233 phosphotransferase Human genes 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 3
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 3
- JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical compound NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 description 3
- FYTLHYRDGXRYEY-UHFFFAOYSA-N 5-Methyl-3-pyrazolamine Chemical compound CC=1C=C(N)NN=1 FYTLHYRDGXRYEY-UHFFFAOYSA-N 0.000 description 3
- YJKJAYFKPIUBAW-UHFFFAOYSA-N 9h-carbazol-1-amine Chemical compound N1C2=CC=CC=C2C2=C1C(N)=CC=C2 YJKJAYFKPIUBAW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229910015845 BBr3 Inorganic materials 0.000 description 3
- PDSFPSRBSMFQGM-UHFFFAOYSA-N CN(C=1OCC(N1)NC=1NN=C(C1)C)C1=CC=CC=C1 Chemical compound CN(C=1OCC(N1)NC=1NN=C(C1)C)C1=CC=CC=C1 PDSFPSRBSMFQGM-UHFFFAOYSA-N 0.000 description 3
- 208000024172 Cardiovascular disease Diseases 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- 206010020751 Hypersensitivity Diseases 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 150000003973 alkyl amines Chemical class 0.000 description 3
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 3
- 230000007815 allergy Effects 0.000 description 3
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 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
- 230000010261 cell growth Effects 0.000 description 3
- 230000036755 cellular response Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000003246 corticosteroid Substances 0.000 description 3
- 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 3
- 125000005202 dialkylaminocarbonyloxy group Chemical group 0.000 description 3
- 125000004639 dihydroindenyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 235000013399 edible fruits Nutrition 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 229940088598 enzyme Drugs 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 230000009229 glucose formation Effects 0.000 description 3
- 230000010030 glucose lowering effect Effects 0.000 description 3
- 239000003102 growth factor Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 3
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 3
- 230000003054 hormonal effect Effects 0.000 description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 3
- 125000001041 indolyl group Chemical group 0.000 description 3
- 229940079322 interferon Drugs 0.000 description 3
- 230000003834 intracellular effect Effects 0.000 description 3
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 3
- 229940043355 kinase inhibitor Drugs 0.000 description 3
- 208000032839 leukemia Diseases 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000004770 neurodegeneration Effects 0.000 description 3
- 208000015122 neurodegenerative disease Diseases 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
- 125000005429 oxyalkyl group Chemical group 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 150000004032 porphyrins Chemical class 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 230000035939 shock Effects 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 235000009518 sodium iodide Nutrition 0.000 description 3
- 239000004575 stone Substances 0.000 description 3
- 239000000375 suspending agent Substances 0.000 description 3
- 230000014616 translation Effects 0.000 description 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- DZFHZTRACJJBGB-UHFFFAOYSA-N 2-(3-methylphenyl)sulfanyl-n-(5-methyl-1h-pyrazol-3-yl)quinazolin-4-amine Chemical compound N1N=C(C)C=C1NC1=NC(SC=2C=C(C)C=CC=2)=NC2=CC=CC=C12 DZFHZTRACJJBGB-UHFFFAOYSA-N 0.000 description 2
- SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 description 2
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 2
- TWJBTHBJYPDRAZ-UHFFFAOYSA-N 3-methyl-n-[4-[4-[(5-methyl-1h-pyrazol-3-yl)amino]quinazolin-2-yl]sulfanylphenyl]butanamide Chemical compound C1=CC(NC(=O)CC(C)C)=CC=C1SC1=NC(NC=2NN=C(C)C=2)=C(C=CC=C2)C2=N1 TWJBTHBJYPDRAZ-UHFFFAOYSA-N 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical group NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 2
- 201000001320 Atherosclerosis Diseases 0.000 description 2
- 102000004000 Aurora Kinase A Human genes 0.000 description 2
- 208000001333 Colorectal Neoplasms Diseases 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- 102000000578 Cyclin-Dependent Kinase Inhibitor p21 Human genes 0.000 description 2
- 108010016788 Cyclin-Dependent Kinase Inhibitor p21 Proteins 0.000 description 2
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 2
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 2
- 108010001483 Glycogen Synthase Proteins 0.000 description 2
- 102000004457 Granulocyte-Macrophage Colony-Stimulating Factor Human genes 0.000 description 2
- 108010017213 Granulocyte-Macrophage Colony-Stimulating Factor Proteins 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 description 2
- 206010062717 Increased upper airway secretion Diseases 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 208000003445 Mouth Neoplasms Diseases 0.000 description 2
- 208000009565 Pharyngeal Neoplasms Diseases 0.000 description 2
- 206010034811 Pharyngeal cancer Diseases 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 201000004681 Psoriasis Diseases 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229940122924 Src inhibitor Drugs 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 244000269722 Thea sinensis Species 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 2
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 2
- 125000005427 anthranyl group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- 239000005441 aurora Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- 230000033228 biological regulation Effects 0.000 description 2
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 2
- 210000000481 breast Anatomy 0.000 description 2
- 125000004452 carbocyclyl group Chemical group 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 230000022131 cell cycle Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 210000001072 colon Anatomy 0.000 description 2
- 229960001334 corticosteroids Drugs 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 125000006612 decyloxy group Chemical group 0.000 description 2
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 description 2
- 239000003623 enhancer Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 230000004190 glucose uptake Effects 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 208000027866 inflammatory disease Diseases 0.000 description 2
- 230000006362 insulin response pathway Effects 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 2
- 230000003902 lesion Effects 0.000 description 2
- 208000012987 lip and oral cavity carcinoma Diseases 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 229960005181 morphine Drugs 0.000 description 2
- KBUQEJGKRADQSV-UHFFFAOYSA-N n-(5-cyclopropyl-1h-pyrazol-3-yl)-2-(3,4-dimethylphenyl)sulfanylquinazolin-4-amine Chemical compound C1=C(C)C(C)=CC=C1SC1=NC(NC=2NN=C(C=2)C2CC2)=C(C=CC=C2)C2=N1 KBUQEJGKRADQSV-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 230000027405 negative regulation of phosphorylation Effects 0.000 description 2
- 210000004126 nerve fiber Anatomy 0.000 description 2
- 239000002547 new drug Substances 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 239000000346 nonvolatile oil Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 150000003891 oxalate salts Chemical class 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 208000026435 phlegm Diseases 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000002504 physiological saline solution Substances 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 229960003975 potassium Drugs 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 239000003197 protein kinase B inhibitor Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 208000037803 restenosis Diseases 0.000 description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- 238000003971 tillage Methods 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- 239000011135 tin Substances 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- 230000014621 translational initiation Effects 0.000 description 2
- CGVQNDZUWCSFFT-UHFFFAOYSA-N $l^{1}-oxidanyloxyethane Chemical group CCO[O] CGVQNDZUWCSFFT-UHFFFAOYSA-N 0.000 description 1
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
- LSPHULWDVZXLIL-UHFFFAOYSA-N (+/-)-Camphoric acid Chemical compound CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 description 1
- OQANPHBRHBJGNZ-FYJGNVAPSA-N (3e)-6-oxo-3-[[4-(pyridin-2-ylsulfamoyl)phenyl]hydrazinylidene]cyclohexa-1,4-diene-1-carboxylic acid Chemical compound C1=CC(=O)C(C(=O)O)=C\C1=N\NC1=CC=C(S(=O)(=O)NC=2N=CC=CC=2)C=C1 OQANPHBRHBJGNZ-FYJGNVAPSA-N 0.000 description 1
- MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- RZFDLDWSAAUYFW-UHFFFAOYSA-N 1,2,3,4,21,23-hexahydroporphyrin Chemical group N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)CCC1C=C1C=CC4=N1 RZFDLDWSAAUYFW-UHFFFAOYSA-N 0.000 description 1
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 1
- KFUSEUYYWQURPO-UHFFFAOYSA-N 1,2-dichloroethene Chemical compound ClC=CCl KFUSEUYYWQURPO-UHFFFAOYSA-N 0.000 description 1
- LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-Bis(diphenylphosphino)propane Substances C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 1
- VMLKTERJLVWEJJ-UHFFFAOYSA-N 1,5-naphthyridine Chemical group C1=CC=NC2=CC=CN=C21 VMLKTERJLVWEJJ-UHFFFAOYSA-N 0.000 description 1
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000004293 19F NMR spectroscopy Methods 0.000 description 1
- QLSWIGRIBOSFMV-UHFFFAOYSA-N 1h-pyrrol-2-amine Chemical compound NC1=CC=CN1 QLSWIGRIBOSFMV-UHFFFAOYSA-N 0.000 description 1
- XKLNOVWDVMWTOB-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1h-carbazole Chemical compound N1C2=CC=CC=C2C2=C1CCCC2 XKLNOVWDVMWTOB-UHFFFAOYSA-N 0.000 description 1
- RFCQDOVPMUSZMN-UHFFFAOYSA-N 2-Naphthalenethiol Chemical compound C1=CC=CC2=CC(S)=CC=C21 RFCQDOVPMUSZMN-UHFFFAOYSA-N 0.000 description 1
- STOVYWBRBMYHPC-KAVGSWPWSA-N 2-[(E)-[(E)-(2-hydroxyphenyl)methylidenehydrazinylidene]methyl]phenol Chemical compound OC1=CC=CC=C1\C=N\N=C\C1=CC=CC=C1O STOVYWBRBMYHPC-KAVGSWPWSA-N 0.000 description 1
- CVAFKCOBXMQVBC-UHFFFAOYSA-N 2-azabicyclo[5.5.0]dodeca-1(12),2,4,6,8,10-hexaene Chemical compound N1=CC=CC=C2C=CC=CC=C21 CVAFKCOBXMQVBC-UHFFFAOYSA-N 0.000 description 1
- VRHFODVXFPJXIQ-UHFFFAOYSA-N 2-chloro-n-(5-methyl-1h-pyrazol-3-yl)-6-phenylpyrimidin-4-amine Chemical compound N1N=C(C)C=C1NC1=CC(C=2C=CC=CC=2)=NC(Cl)=N1 VRHFODVXFPJXIQ-UHFFFAOYSA-N 0.000 description 1
- GWEOBKYRGURQCQ-UHFFFAOYSA-N 2-chloro-n-(5-methyl-1h-pyrazol-3-yl)quinazolin-4-amine Chemical compound N1N=C(C)C=C1NC1=NC(Cl)=NC2=CC=CC=C12 GWEOBKYRGURQCQ-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- LEACJMVNYZDSKR-UHFFFAOYSA-N 2-octyldodecan-1-ol Chemical compound CCCCCCCCCCC(CO)CCCCCCCC LEACJMVNYZDSKR-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 description 1
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 1
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 1
- 229940105325 3-dimethylaminopropylamine Drugs 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical compound [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical class OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
- DUIMWXDLDBNUFD-UHFFFAOYSA-N 4-pyrimidin-2-ylmorpholine Chemical compound C1COCCN1C1=NC=CC=N1 DUIMWXDLDBNUFD-UHFFFAOYSA-N 0.000 description 1
- 125000004487 4-tetrahydropyranyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- SONANLOEVWRBAO-UHFFFAOYSA-N 5-amino-1,2-dihydropyrazole-3-thione Chemical compound NC1=CC(S)=NN1 SONANLOEVWRBAO-UHFFFAOYSA-N 0.000 description 1
- MXVAGCQKBDMKPG-UHFFFAOYSA-N 5-cyclopropyl-1h-pyrazol-3-amine Chemical compound N1C(N)=CC(C2CC2)=N1 MXVAGCQKBDMKPG-UHFFFAOYSA-N 0.000 description 1
- IOCFAKAQESPBGT-UHFFFAOYSA-N 5-cyclopropylpyridin-3-amine Chemical compound NC1=CN=CC(C2CC2)=C1 IOCFAKAQESPBGT-UHFFFAOYSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 102000004146 ATP citrate synthases Human genes 0.000 description 1
- 108090000662 ATP citrate synthases Proteins 0.000 description 1
- 206010000117 Abnormal behaviour Diseases 0.000 description 1
- OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229940100578 Acetylcholinesterase inhibitor Drugs 0.000 description 1
- 208000010507 Adenocarcinoma of Lung Diseases 0.000 description 1
- 208000003200 Adenoma Diseases 0.000 description 1
- 206010001233 Adenoma benign Diseases 0.000 description 1
- 229940126638 Akt inhibitor Drugs 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 102000013455 Amyloid beta-Peptides Human genes 0.000 description 1
- 108010090849 Amyloid beta-Peptides Proteins 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- FMMWHPNWAFZXNH-UHFFFAOYSA-N Benz[a]pyrene Chemical compound C1=C2C3=CC=CC=C3C=C(C=C3)C2=C2C3=CC=CC2=C1 FMMWHPNWAFZXNH-UHFFFAOYSA-N 0.000 description 1
- 229940123208 Biguanide Drugs 0.000 description 1
- 208000020925 Bipolar disease Diseases 0.000 description 1
- 206010005003 Bladder cancer Diseases 0.000 description 1
- 201000004569 Blindness Diseases 0.000 description 1
- 102000004506 Blood Proteins Human genes 0.000 description 1
- 108010017384 Blood Proteins Proteins 0.000 description 1
- 208000019838 Blood disease Diseases 0.000 description 1
- 206010005949 Bone cancer Diseases 0.000 description 1
- 208000018084 Bone neoplasm Diseases 0.000 description 1
- 208000003174 Brain Neoplasms Diseases 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- ZIORDBHVUVJBIL-UHFFFAOYSA-N CCCCCCCCCN(CCCCCCCCC)C(C)C(O)=O Chemical group CCCCCCCCCN(CCCCCCCCC)C(C)C(O)=O ZIORDBHVUVJBIL-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 201000009030 Carcinoma Diseases 0.000 description 1
- 206010008342 Cervix carcinoma Diseases 0.000 description 1
- 229920001268 Cholestyramine Polymers 0.000 description 1
- 241000723346 Cinnamomum camphora Species 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
- OMPIYDSYGYKWSG-UHFFFAOYSA-N Citronensaeure-alpha-aethylester Chemical class CCOC(=O)CC(O)(C(O)=O)CC(O)=O OMPIYDSYGYKWSG-UHFFFAOYSA-N 0.000 description 1
- 102000005636 Cyclic AMP Response Element-Binding Protein Human genes 0.000 description 1
- 108010045171 Cyclic AMP Response Element-Binding Protein Proteins 0.000 description 1
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 1
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 description 1
- 229930105110 Cyclosporin A Natural products 0.000 description 1
- 108010036949 Cyclosporine Proteins 0.000 description 1
- 102000004127 Cytokines Human genes 0.000 description 1
- 108090000695 Cytokines Proteins 0.000 description 1
- 241000701022 Cytomegalovirus Species 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
- 102100030013 Endoribonuclease Human genes 0.000 description 1
- 101710199605 Endoribonuclease Proteins 0.000 description 1
- 241000792859 Enema Species 0.000 description 1
- 208000000461 Esophageal Neoplasms Diseases 0.000 description 1
- 240000006570 Euonymus japonicus Species 0.000 description 1
- 235000016796 Euonymus japonicus Nutrition 0.000 description 1
- 108010007457 Extracellular Signal-Regulated MAP Kinases Proteins 0.000 description 1
- 102000018233 Fibroblast Growth Factor Human genes 0.000 description 1
- 108050007372 Fibroblast Growth Factor Proteins 0.000 description 1
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 206010018364 Glomerulonephritis Diseases 0.000 description 1
- 229920002306 Glycocalyx Polymers 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 1
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 1
- 206010019842 Hepatomegaly Diseases 0.000 description 1
- 101001050288 Homo sapiens Transcription factor Jun Proteins 0.000 description 1
- 102000008100 Human Serum Albumin Human genes 0.000 description 1
- 108091006905 Human Serum Albumin Proteins 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 208000037147 Hypercalcaemia Diseases 0.000 description 1
- 206010020880 Hypertrophy Diseases 0.000 description 1
- 208000013016 Hypoglycemia Diseases 0.000 description 1
- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 1
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 1
- 108010002352 Interleukin-1 Proteins 0.000 description 1
- 108010063738 Interleukins Proteins 0.000 description 1
- 102000015696 Interleukins Human genes 0.000 description 1
- 102000004310 Ion Channels Human genes 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- UETNIIAIRMUTSM-UHFFFAOYSA-N Jacareubin Natural products CC1(C)OC2=CC3Oc4c(O)c(O)ccc4C(=O)C3C(=C2C=C1)O UETNIIAIRMUTSM-UHFFFAOYSA-N 0.000 description 1
- 208000008839 Kidney Neoplasms Diseases 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- 206010023825 Laryngeal cancer Diseases 0.000 description 1
- 206010062038 Lip neoplasm Diseases 0.000 description 1
- 239000012448 Lithium borohydride Substances 0.000 description 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
- 206010027452 Metastases to bone Diseases 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical group CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 101710115937 Microtubule-associated protein tau Proteins 0.000 description 1
- 102100040243 Microtubule-associated protein tau Human genes 0.000 description 1
- 241001529936 Murinae Species 0.000 description 1
- 208000010428 Muscle Weakness Diseases 0.000 description 1
- 206010028372 Muscular weakness Diseases 0.000 description 1
- 102100038895 Myc proto-oncogene protein Human genes 0.000 description 1
- 101710135898 Myc proto-oncogene protein Proteins 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 108010025020 Nerve Growth Factor Proteins 0.000 description 1
- 102000007072 Nerve Growth Factors Human genes 0.000 description 1
- 208000012902 Nervous system disease Diseases 0.000 description 1
- 206010029260 Neuroblastoma Diseases 0.000 description 1
- 208000025966 Neurological disease Diseases 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical class OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 206010030155 Oesophageal carcinoma Diseases 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 108700020796 Oncogene Proteins 0.000 description 1
- 208000010191 Osteitis Deformans Diseases 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 1
- YXLXNENXOJSQEI-UHFFFAOYSA-L Oxine-copper Chemical compound [Cu+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 YXLXNENXOJSQEI-UHFFFAOYSA-L 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229910019213 POCl3 Inorganic materials 0.000 description 1
- 229930012538 Paclitaxel Natural products 0.000 description 1
- 208000027868 Paget disease Diseases 0.000 description 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 102000005877 Peptide Initiation Factors Human genes 0.000 description 1
- 108010044843 Peptide Initiation Factors Proteins 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 206010060862 Prostate cancer Diseases 0.000 description 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
- 102000001708 Protein Isoforms Human genes 0.000 description 1
- 108010029485 Protein Isoforms Proteins 0.000 description 1
- 102000009096 Proto-Oncogene Proteins c-myb Human genes 0.000 description 1
- 108010087776 Proto-Oncogene Proteins c-myb Proteins 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
- 101100163890 Rattus norvegicus Ascl2 gene Proteins 0.000 description 1
- 208000015634 Rectal Neoplasms Diseases 0.000 description 1
- 206010038389 Renal cancer Diseases 0.000 description 1
- FTALBRSUTCGOEG-UHFFFAOYSA-N Riluzole Chemical compound C1=C(OC(F)(F)F)C=C2SC(N)=NC2=C1 FTALBRSUTCGOEG-UHFFFAOYSA-N 0.000 description 1
- 229910006074 SO2NH2 Inorganic materials 0.000 description 1
- 206010039491 Sarcoma Diseases 0.000 description 1
- DYAHQFWOVKZOOW-UHFFFAOYSA-N Sarin Chemical compound CC(C)OP(C)(F)=O DYAHQFWOVKZOOW-UHFFFAOYSA-N 0.000 description 1
- 101710113029 Serine/threonine-protein kinase Proteins 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 208000000453 Skin Neoplasms Diseases 0.000 description 1
- 102100037442 Small conductance calcium-activated potassium channel protein 3 Human genes 0.000 description 1
- 235000014459 Sorbus Nutrition 0.000 description 1
- 241001092391 Sorbus Species 0.000 description 1
- 208000005392 Spasm Diseases 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- 208000024313 Testicular Neoplasms Diseases 0.000 description 1
- 206010057644 Testis cancer Diseases 0.000 description 1
- 208000024770 Thyroid neoplasm Diseases 0.000 description 1
- 206010062129 Tongue neoplasm Diseases 0.000 description 1
- 108091023040 Transcription factor Proteins 0.000 description 1
- 102000040945 Transcription factor Human genes 0.000 description 1
- 102100023132 Transcription factor Jun Human genes 0.000 description 1
- 101710150448 Transcriptional regulator Myc Proteins 0.000 description 1
- 102000004887 Transforming Growth Factor beta Human genes 0.000 description 1
- 108090001012 Transforming Growth Factor beta Proteins 0.000 description 1
- 206010052779 Transplant rejections Diseases 0.000 description 1
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical class CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 description 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 description 1
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- AHIBWURJLGCHAY-UHFFFAOYSA-N [S].C1=CC=CC=C1 Chemical compound [S].C1=CC=CC=C1 AHIBWURJLGCHAY-UHFFFAOYSA-N 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 206010059394 acanthoma Diseases 0.000 description 1
- 229920006397 acrylic thermoplastic Polymers 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 208000009956 adenocarcinoma Diseases 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 239000003732 agents acting on the eye Substances 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000005055 alkyl alkoxy group Chemical group 0.000 description 1
- 125000000278 alkyl amino alkyl group Chemical group 0.000 description 1
- 125000005195 alkyl amino carbonyloxy group Chemical group 0.000 description 1
- 125000001118 alkylidene group Chemical group 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
- 229940063655 aluminum stearate Drugs 0.000 description 1
- 230000001668 ameliorated effect Effects 0.000 description 1
- 229940024606 amino acid Drugs 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 238000001949 anaesthesia Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000033115 angiogenesis Effects 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 1
- IPQGOTUZADECCY-UHFFFAOYSA-N anthracene-2-sulfonic acid Chemical compound C1=CC=CC2=CC3=CC(S(=O)(=O)O)=CC=C3C=C21 IPQGOTUZADECCY-UHFFFAOYSA-N 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000001028 anti-proliverative effect Effects 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 239000000063 antileukemic agent Substances 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940125688 antiparkinson agent Drugs 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 1
- 125000005160 aryl oxy alkyl group Chemical group 0.000 description 1
- 229940009098 aspartate Drugs 0.000 description 1
- 230000003416 augmentation Effects 0.000 description 1
- LMEKQMALGUDUQG-UHFFFAOYSA-N azathioprine Chemical compound CN1C=NC([N+]([O-])=O)=C1SC1=NC=NC2=C1NC=N2 LMEKQMALGUDUQG-UHFFFAOYSA-N 0.000 description 1
- 229960002170 azathioprine Drugs 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 229960000686 benzalkonium chloride Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
- 229940050390 benzoate Drugs 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 description 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 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
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
- 125000000638 benzylaminocarbonyl group Chemical group C(C1=CC=CC=C1)NC(=O)* 0.000 description 1
- 150000004283 biguanides Chemical class 0.000 description 1
- 201000009036 biliary tract cancer Diseases 0.000 description 1
- 208000020790 biliary tract neoplasm Diseases 0.000 description 1
- 230000008236 biological pathway Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 238000001574 biopsy Methods 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 210000001124 body fluid Anatomy 0.000 description 1
- 239000010839 body fluid Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 208000015322 bone marrow disease Diseases 0.000 description 1
- 210000000133 brain stem Anatomy 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical group [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 230000011712 cell development Effects 0.000 description 1
- 230000024245 cell differentiation Effects 0.000 description 1
- 230000008727 cellular glucose uptake Effects 0.000 description 1
- 230000019522 cellular metabolic process Effects 0.000 description 1
- 230000005754 cellular signaling Effects 0.000 description 1
- 208000015114 central nervous system disease Diseases 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 201000010881 cervical cancer Diseases 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- BJDCWCLMFKKGEE-CMDXXVQNSA-N chembl252518 Chemical compound C([C@@](OO1)(C)O2)C[C@H]3[C@H](C)CC[C@@H]4[C@@]31[C@@H]2O[C@H](O)[C@@H]4C BJDCWCLMFKKGEE-CMDXXVQNSA-N 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000544 cholinesterase inhibitor Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 210000000349 chromosome Anatomy 0.000 description 1
- 229960001265 ciclosporin Drugs 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- TXGVDTJWMZUNMP-UHFFFAOYSA-N cyclodecanamine Chemical compound NC1CCCCCCCCC1 TXGVDTJWMZUNMP-UHFFFAOYSA-N 0.000 description 1
- MRKZAZMYXYSBDG-UHFFFAOYSA-N cyclopentyl propanoate Chemical class CCC(=O)OC1CCCC1 MRKZAZMYXYSBDG-UHFFFAOYSA-N 0.000 description 1
- 229960004397 cyclophosphamide Drugs 0.000 description 1
- 229930182912 cyclosporin Natural products 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 229940079919 digestives enzyme preparation Drugs 0.000 description 1
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical class CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 230000002124 endocrine Effects 0.000 description 1
- 239000007920 enema Substances 0.000 description 1
- 229940095399 enema Drugs 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000002532 enzyme inhibitor Substances 0.000 description 1
- 229960003276 erythromycin Drugs 0.000 description 1
- 201000004101 esophageal cancer Diseases 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- 229940057975 ethyl citrate Drugs 0.000 description 1
- 230000000763 evoking effect Effects 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 210000002950 fibroblast Anatomy 0.000 description 1
- 229940126864 fibroblast growth factor Drugs 0.000 description 1
- 206010016629 fibroma Diseases 0.000 description 1
- 150000002220 fluorenes Chemical class 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 229960002949 fluorouracil Drugs 0.000 description 1
- 235000011194 food seasoning agent Nutrition 0.000 description 1
- 238000002309 gasification Methods 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 102000034356 gene-regulatory proteins Human genes 0.000 description 1
- 108091006104 gene-regulatory proteins Proteins 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 208000005017 glioblastoma Diseases 0.000 description 1
- 230000004153 glucose metabolism Effects 0.000 description 1
- 210000004517 glycocalyx Anatomy 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 125000000262 haloalkenyl group Chemical group 0.000 description 1
- 125000004438 haloalkoxy group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000003862 health status Effects 0.000 description 1
- 208000014951 hematologic disease Diseases 0.000 description 1
- 208000018706 hematopoietic system disease Diseases 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
- 150000002386 heptoses Chemical class 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- DALYXJVFSIYXMA-UHFFFAOYSA-N hydrogen sulfide dimer Chemical compound S.S DALYXJVFSIYXMA-UHFFFAOYSA-N 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical class 0.000 description 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 1
- 230000000148 hypercalcaemia Effects 0.000 description 1
- 208000030915 hypercalcemia disease Diseases 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 230000003053 immunization Effects 0.000 description 1
- 238000002649 immunization Methods 0.000 description 1
- 229940125721 immunosuppressive agent Drugs 0.000 description 1
- 239000003018 immunosuppressive agent Substances 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000005462 in vivo assay Methods 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 229940097275 indigo Drugs 0.000 description 1
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 description 1
- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical compound C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229940047124 interferons Drugs 0.000 description 1
- 238000007917 intracranial administration Methods 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000007919 intrasynovial administration Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 208000028867 ischemia Diseases 0.000 description 1
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 201000010982 kidney cancer Diseases 0.000 description 1
- 208000017169 kidney disease Diseases 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 208000003849 large cell carcinoma Diseases 0.000 description 1
- 206010023841 laryngeal neoplasm Diseases 0.000 description 1
- 201000010901 lateral sclerosis Diseases 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 201000006721 lip cancer Diseases 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 201000007270 liver cancer Diseases 0.000 description 1
- 208000019423 liver disease Diseases 0.000 description 1
- 208000014018 liver neoplasm Diseases 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 201000005249 lung adenocarcinoma Diseases 0.000 description 1
- 201000005202 lung cancer Diseases 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- 230000001926 lymphatic effect Effects 0.000 description 1
- 210000004324 lymphatic system Anatomy 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- SCEZYJKGDJPHQO-UHFFFAOYSA-M magnesium;methanidylbenzene;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C1=CC=CC=C1 SCEZYJKGDJPHQO-UHFFFAOYSA-M 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 1
- 208000027202 mammary Paget disease Diseases 0.000 description 1
- 210000001595 mastoid Anatomy 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Chemical class 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- HPNSFSBZBAHARI-UHFFFAOYSA-N micophenolic acid Natural products OC1=C(CC=C(C)CCC(O)=O)C(OC)=C(C)C2=C1C(=O)OC2 HPNSFSBZBAHARI-UHFFFAOYSA-N 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000011278 mitosis Effects 0.000 description 1
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 description 1
- 125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 description 1
- 208000005264 motor neuron disease Diseases 0.000 description 1
- 230000004118 muscle contraction Effects 0.000 description 1
- 229940014456 mycophenolate Drugs 0.000 description 1
- HPNSFSBZBAHARI-RUDMXATFSA-N mycophenolic acid Chemical compound OC1=C(C\C=C(/C)CCC(O)=O)C(OC)=C(C)C2=C1C(=O)OC2 HPNSFSBZBAHARI-RUDMXATFSA-N 0.000 description 1
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical group N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 1
- AYEQJLOHMLYKAV-UHFFFAOYSA-N n-(4-sulfanylphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(S)C=C1 AYEQJLOHMLYKAV-UHFFFAOYSA-N 0.000 description 1
- JKJAHADIQYGLNH-UHFFFAOYSA-N n-[4-[4-[(5-methyl-1h-pyrazol-3-yl)amino]quinazolin-2-yl]sulfanylphenyl]propane-2-sulfonamide Chemical compound C1=CC(NS(=O)(=O)C(C)C)=CC=C1SC1=NC(NC=2NN=C(C)C=2)=C(C=CC=C2)C2=N1 JKJAHADIQYGLNH-UHFFFAOYSA-N 0.000 description 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- ZCEKUVXWYVCXST-UHFFFAOYSA-N n-sulfanylacetamide Chemical compound CC(=O)NS ZCEKUVXWYVCXST-UHFFFAOYSA-N 0.000 description 1
- 239000007922 nasal spray Substances 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 210000002682 neurofibrillary tangle Anatomy 0.000 description 1
- 230000016273 neuron death Effects 0.000 description 1
- 239000003900 neurotrophic factor Substances 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- 231100000344 non-irritating Toxicity 0.000 description 1
- 239000002777 nucleoside Substances 0.000 description 1
- 210000004940 nucleus Anatomy 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 230000000771 oncological effect Effects 0.000 description 1
- 229940023490 ophthalmic product Drugs 0.000 description 1
- 239000007935 oral tablet Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 150000002918 oxazolines Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 229960001592 paclitaxel Drugs 0.000 description 1
- 230000036407 pain Effects 0.000 description 1
- 201000002528 pancreatic cancer Diseases 0.000 description 1
- 208000008443 pancreatic carcinoma Diseases 0.000 description 1
- 229960005489 paracetamol Drugs 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 210000003200 peritoneal cavity Anatomy 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- DHHVAGZRUROJKS-UHFFFAOYSA-N phentermine Chemical compound CC(C)(N)CC1=CC=CC=C1 DHHVAGZRUROJKS-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical class CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229950008882 polysorbate Drugs 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- RKCAIXNGYQCCAL-UHFFFAOYSA-N porphin Chemical compound N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 RKCAIXNGYQCCAL-UHFFFAOYSA-N 0.000 description 1
- 239000001508 potassium citrate Substances 0.000 description 1
- 229960002635 potassium citrate Drugs 0.000 description 1
- QEEAPRPFLLJWCF-UHFFFAOYSA-K potassium citrate (anhydrous) Chemical compound [K+].[K+].[K+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QEEAPRPFLLJWCF-UHFFFAOYSA-K 0.000 description 1
- 235000011082 potassium citrates Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000037452 priming Effects 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000009822 protein phosphorylation Effects 0.000 description 1
- 238000001243 protein synthesis Methods 0.000 description 1
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 description 1
- BWESROVQGZSBRX-UHFFFAOYSA-N pyrido[3,2-d]pyrimidine Chemical group C1=NC=NC2=CC=CN=C21 BWESROVQGZSBRX-UHFFFAOYSA-N 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 206010038038 rectal cancer Diseases 0.000 description 1
- 229940100618 rectal suppository Drugs 0.000 description 1
- 239000006215 rectal suppository Substances 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 201000001275 rectum cancer Diseases 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000022983 regulation of cell cycle Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 229960004181 riluzole Drugs 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 210000003296 saliva Anatomy 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 201000000849 skin cancer Diseases 0.000 description 1
- 208000000649 small cell carcinoma Diseases 0.000 description 1
- 201000002314 small intestine cancer Diseases 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 206010041823 squamous cell carcinoma Diseases 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 229960001940 sulfasalazine Drugs 0.000 description 1
- NCEXYHBECQHGNR-UHFFFAOYSA-N sulfasalazine Natural products C1=C(O)C(C(=O)O)=CC(N=NC=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-UHFFFAOYSA-N 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 238000002636 symptomatic treatment Methods 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 1
- 210000001138 tear Anatomy 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 201000003120 testicular cancer Diseases 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- ZRKFYGHZFMAOKI-QMGMOQQFSA-N tgfbeta Chemical compound C([C@H](NC(=O)[C@H](C(C)C)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)CCSC)C(C)C)[C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(O)=O)C1=CC=C(O)C=C1 ZRKFYGHZFMAOKI-QMGMOQQFSA-N 0.000 description 1
- 229940124788 therapeutic inhibitor Drugs 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 201000002510 thyroid cancer Diseases 0.000 description 1
- 208000030901 thyroid gland follicular carcinoma Diseases 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 201000006134 tongue cancer Diseases 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
- 239000001226 triphosphate Substances 0.000 description 1
- 235000011178 triphosphate Nutrition 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical class CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 201000005112 urinary bladder cancer Diseases 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- 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
-
- 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
- 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
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- 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
- A61P17/14—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
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
-
- 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
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
- 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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
- A61P3/14—Drugs for disorders of the metabolism for electrolyte homeostasis for calcium homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- 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
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/18—Drugs for disorders of the endocrine system of the parathyroid hormones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/16—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Biomedical Technology (AREA)
- Diabetes (AREA)
- Virology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Oncology (AREA)
- Endocrinology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Communicable Diseases (AREA)
- Pulmonology (AREA)
- Molecular Biology (AREA)
- Psychiatry (AREA)
- Obesity (AREA)
- Pain & Pain Management (AREA)
- Biotechnology (AREA)
- Emergency Medicine (AREA)
- Urology & Nephrology (AREA)
- Hospice & Palliative Care (AREA)
- Psychology (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25788700P | 2000-12-21 | 2000-12-21 | |
| US28694901P | 2001-04-27 | 2001-04-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200716617A TW200716617A (en) | 2007-05-01 |
| TWI313269B true TWI313269B (en) | 2009-08-11 |
Family
ID=26946273
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW095139649A TWI313269B (en) | 2000-12-21 | 2001-12-25 | Pyrazole compounds useful as protein kinase inhibitors |
| TW090131846A TWI290551B (en) | 2000-12-21 | 2001-12-25 | Pyrazole compounds useful as protein kinase inhibitors |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW090131846A TWI290551B (en) | 2000-12-21 | 2001-12-25 | Pyrazole compounds useful as protein kinase inhibitors |
Country Status (27)
| Country | Link |
|---|---|
| US (16) | US6653300B2 (OSRAM) |
| EP (10) | EP1345925B1 (OSRAM) |
| JP (19) | JP4160392B2 (OSRAM) |
| KR (8) | KR20030061858A (OSRAM) |
| CN (6) | CN102250071A (OSRAM) |
| AP (2) | AP2003002825A0 (OSRAM) |
| AR (4) | AR042169A1 (OSRAM) |
| AT (9) | ATE327989T1 (OSRAM) |
| AU (7) | AU2001297619B2 (OSRAM) |
| BR (2) | BR0116493A (OSRAM) |
| CA (8) | CA2432131C (OSRAM) |
| CY (1) | CY1106297T1 (OSRAM) |
| DE (8) | DE60119775T2 (OSRAM) |
| DK (3) | DK1355905T3 (OSRAM) |
| ES (7) | ES2375491T3 (OSRAM) |
| HU (5) | HUP0400842A2 (OSRAM) |
| IL (8) | IL156369A0 (OSRAM) |
| MX (8) | MXPA03005609A (OSRAM) |
| MY (1) | MY140377A (OSRAM) |
| NO (5) | NO20032671L (OSRAM) |
| NZ (8) | NZ526468A (OSRAM) |
| PL (2) | PL210414B1 (OSRAM) |
| PT (3) | PT1355905E (OSRAM) |
| RU (1) | RU2355688C2 (OSRAM) |
| SI (2) | SI1353916T1 (OSRAM) |
| TW (2) | TWI313269B (OSRAM) |
| WO (8) | WO2002066461A1 (OSRAM) |
Families Citing this family (379)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6982260B1 (en) | 1999-11-22 | 2006-01-03 | Warner-Lambert Company | Quinazolines and their use for inhibiting cyclin-dependent kinase enzymes |
| US7473691B2 (en) * | 2000-09-15 | 2009-01-06 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| US6660731B2 (en) * | 2000-09-15 | 2003-12-09 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| WO2002022605A1 (en) * | 2000-09-15 | 2002-03-21 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| MXPA03005001A (es) * | 2000-12-05 | 2003-09-05 | Vertex Pharma | Inhibidores de n- terminal c-jun cinasas (jnk) y otras proteinas cinasas. |
| AP2003002825A0 (en) * | 2000-12-21 | 2003-09-30 | Vertex Pharma | Pyrazole compounds useful as protein kinase inhibitors |
| AU2002250394A1 (en) * | 2001-03-23 | 2002-10-08 | Bayer Corporation | Rho-kinase inhibitors |
| ATE400274T1 (de) | 2001-04-10 | 2008-07-15 | Merck & Co Inc | Hemmstoffe der akt aktivität |
| US7105667B2 (en) * | 2001-05-01 | 2006-09-12 | Bristol-Myers Squibb Co. | Fused heterocyclic compounds and use thereof |
| US7138404B2 (en) * | 2001-05-23 | 2006-11-21 | Hoffmann-La Roche Inc. | 4-aminopyrimidine derivatives |
| US7115617B2 (en) | 2001-08-22 | 2006-10-03 | Amgen Inc. | Amino-substituted pyrimidinyl derivatives and methods of use |
| US6939874B2 (en) | 2001-08-22 | 2005-09-06 | Amgen Inc. | Substituted pyrimidinyl derivatives and methods of use |
| WO2003026666A1 (en) * | 2001-09-26 | 2003-04-03 | Bayer Pharmaceuticals Corporation | 2-phenylamino-4- (5-pyrazolylamino)-pyrimidine derivatives as kinase inhibitors, in particular, as src kinase inhibitors |
| NZ531765A (en) * | 2001-09-26 | 2006-02-24 | Pharmacia Italia S | Aminoindazole derivatives active as kinase inhibitors, process for their preparation and pharmaceutical compositions containing them |
| SE0104140D0 (sv) * | 2001-12-07 | 2001-12-07 | Astrazeneca Ab | Novel Compounds |
| US20030187026A1 (en) | 2001-12-13 | 2003-10-02 | Qun Li | Kinase inhibitors |
| AU2002361846A1 (en) * | 2001-12-21 | 2003-07-15 | Bayer Pharmaceuticals Corporation | Quinazoline and quinoline derivative compounds as inhibitors of prolylpeptidase, inducers of apoptosis and cancer treatment agents |
| CA2471565C (en) | 2002-01-10 | 2009-10-27 | Patricia Ann Day-Lollini | Use of a gsk-3beta inhibitor in the manufacture of a medicament for increasing bone formation |
| TWI329105B (en) | 2002-02-01 | 2010-08-21 | Rigel Pharmaceuticals Inc | 2,4-pyrimidinediamine compounds and their uses |
| WO2003066629A2 (en) * | 2002-02-06 | 2003-08-14 | Vertex Pharmaceuticals Incorporated | Heteroaryl compounds useful as inhibitors of gsk-3 |
| US20040009981A1 (en) | 2002-03-15 | 2004-01-15 | David Bebbington | Compositions useful as inhibitors of protein kinases |
| US7179826B2 (en) | 2002-03-15 | 2007-02-20 | Vertex Pharmaceuticals Incorporated | Compositions useful as inhibitors of protein kinases |
| US7091343B2 (en) | 2002-03-15 | 2006-08-15 | Vertex Pharmaceuticals Incorporated | Compositions useful as inhibitors of protein kinases |
| AU2003223467B2 (en) | 2002-04-08 | 2007-10-04 | Merck Sharp & Dohme Corp. | Inhibitors of Akt activity |
| US7524852B2 (en) | 2002-06-07 | 2009-04-28 | Kyowa Hakko Kogyo Co., Ltd. | Bicyclic pyrimidine derivatives |
| MY141867A (en) * | 2002-06-20 | 2010-07-16 | Vertex Pharma | Substituted pyrimidines useful as protein kinase inhibitors |
| JP2005536517A (ja) * | 2002-07-23 | 2005-12-02 | スミスクライン ビーチャム コーポレーション | キナーゼインヒビターとしてのピラゾロピリミジン |
| IL166241A0 (en) | 2002-07-29 | 2006-01-15 | Rigel Pharmaceuticals Inc | Method of treating or preventing autoimmune diseases with 2,4-pyrimidinedinediamine compounds |
| EP1739087A1 (en) * | 2002-08-02 | 2007-01-03 | Vertex Pharmaceuticals Incorporated | Pyrazole compositions useful as inhibitors of gsk-3 |
| ATE339419T1 (de) | 2002-08-02 | 2006-10-15 | Vertex Pharma | Pyrazolenthaltende zusammensetzungen und ihre verwendung als gsk-3 inhibitoren |
| FR2844267B1 (fr) * | 2002-09-05 | 2008-02-15 | Aventis Pharma Sa | Nouveaux derives d'aminoindazoles a titre de medicaments et compositions pharmaceutiques les renfermant |
| MXPA05001807A (es) | 2002-09-05 | 2005-04-19 | Aventis Pharma Sa | Nuevos derivados de aminoindazol utilizados como medicamentos y composiciones farmaceuticas que los contienen. |
| AU2003255482A1 (en) * | 2002-10-02 | 2004-04-23 | Merck Patent Gmbh | Use of 4 amino-quinazolines as anti cancer agents |
| NZ539211A (en) * | 2002-10-04 | 2008-05-30 | Prana Biotechnology Ltd | Neurologically-active compounds |
| KR100490893B1 (ko) * | 2002-10-11 | 2005-05-23 | (주) 비엔씨바이오팜 | 2-메톡시-1,3,5-트리아진 유도체, 그 제조방법 및 이를 포함하는 항바이러스용 약학적 조성물 |
| GB0226583D0 (en) * | 2002-11-14 | 2002-12-18 | Cyclacel Ltd | Compounds |
| US7309701B2 (en) | 2002-11-19 | 2007-12-18 | Sanofi-Aventis Deutschland Gmbh | Pyridazinone derivatives as pharmaceuticals and pharmaceutical compositions containing them |
| US7462613B2 (en) | 2002-11-19 | 2008-12-09 | Sanofi-Aventis Deutschland Gmbh | Pyridazinone derivatives as pharmaceuticals and pharmaceutical compositions containing them |
| FR2847253B1 (fr) * | 2002-11-19 | 2007-05-18 | Aventis Pharma Sa | Nouveaux derives de pyridazinones a titre de medicaments et compositions pharmaceutiques les renfermant |
| JP4673218B2 (ja) * | 2002-11-21 | 2011-04-20 | ノバルティス バクシンズ アンド ダイアグノスティックス,インコーポレーテッド | ホスホチジルイノシトール(pi)3−キナーゼインヒビターとしての2,4,6−三置換ピリミジン、および癌の処置におけるその使用 |
| WO2004072029A2 (en) * | 2003-02-06 | 2004-08-26 | Vertex Pharmaceuticals Incorporated | Pyrazolopyridazines useful as inhibitors of protein kinases |
| US7157455B2 (en) * | 2003-02-10 | 2007-01-02 | Hoffmann-La Roche Inc. | 4-Aminopyrimidine-5-one derivatives |
| EP1644338A1 (en) * | 2003-04-01 | 2006-04-12 | Aponetics AG | 2, 4, 6-trisubstituted pyrimidine derivatives useful for the treatment of neoplastic and autoimmune diseases |
| EP1635837B1 (en) * | 2003-06-02 | 2008-07-16 | AstraZeneca AB | (3-((quinazolin-4-yl)amino)-1h-pyrazol-1-yl)acetamide derivatives and related compounds as aurora kinase inhibitors for the treatment of proliferative diseases such as cancer |
| US7560467B2 (en) | 2003-06-19 | 2009-07-14 | Smithkline Beecham Corporation | Indazolo-tetrahydropyrimidine-carboxamide derivative kinase inhibitors |
| US8309562B2 (en) | 2003-07-03 | 2012-11-13 | Myrexis, Inc. | Compounds and therapeutical use thereof |
| KR101218213B1 (ko) * | 2003-07-03 | 2013-01-04 | 시토비아 인크. | 카스파제의 활성인자 및 세포자멸사의 유도인자로서의4-아릴아미노-퀴나졸린 |
| TWI372050B (en) * | 2003-07-03 | 2012-09-11 | Astex Therapeutics Ltd | (morpholin-4-ylmethyl-1h-benzimidazol-2-yl)-1h-pyrazoles |
| GB0315966D0 (en) * | 2003-07-08 | 2003-08-13 | Cyclacel Ltd | Compounds |
| BRPI0412259B1 (pt) | 2003-07-22 | 2019-08-20 | Astex Therapeutics Limited | Compostos de 1H-pirazol 3,4-dissubstituídos como moduladores de quinases dependentes de ciclina (CDK), seus usos, processo para a preparação dos mesmos e composição farmacêutica |
| RS53109B (sr) | 2003-07-30 | 2014-06-30 | Rigel Pharmaceuticals Inc. | Jedinjenja 2,4 pirimidindiamina za upotrebu u tretmanu ili prevenciji autoimunih bolesti |
| AU2004261484A1 (en) * | 2003-07-30 | 2005-02-10 | Cyclacel Limited | 2-aminophenyl-4-phenylpyrimidines as kinase inhibitors |
| US20050221357A1 (en) * | 2003-09-19 | 2005-10-06 | Mark Shannon | Normalization of gene expression data |
| US20060024690A1 (en) * | 2003-09-19 | 2006-02-02 | Kao H P | Normalization of data using controls |
| US7417726B2 (en) * | 2003-09-19 | 2008-08-26 | Applied Biosystems Inc. | Normalization of data using controls |
| WO2005030131A2 (en) * | 2003-09-23 | 2005-04-07 | Replidyne, Inc | Bis-quinazoline compounds for the treatment of bacterial infections |
| KR20060123164A (ko) | 2003-10-17 | 2006-12-01 | 아스트라제네카 아베 | 암 치료에 사용하기 위한 4-(피라졸-3-일아미노)피리미딘유도체 |
| JP2007513184A (ja) * | 2003-12-04 | 2007-05-24 | バーテックス ファーマシューティカルズ インコーポレイテッド | プロテインキナーゼのインヒビターとして有用なキノキサリン |
| MXPA06006532A (es) * | 2003-12-09 | 2006-08-23 | Vertex Pharma | Derivados de naftiridina y su uso como moduladores de receptores muscarinicos. |
| WO2005061519A1 (en) | 2003-12-19 | 2005-07-07 | Takeda San Diego, Inc. | Kinase inhibitors |
| TW200530235A (en) | 2003-12-24 | 2005-09-16 | Renovis Inc | Bicycloheteroarylamine compounds as ion channel ligands and uses thereof |
| CA2556239A1 (en) | 2004-02-11 | 2005-08-25 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments |
| EP1723427A2 (en) * | 2004-02-26 | 2006-11-22 | Bayer HealthCare AG | Diagnostics and therapeutics for diseases associated with glycogen synthase kinase 3 beta (gsk3b) |
| WO2005087710A1 (ja) * | 2004-03-15 | 2005-09-22 | Takeda Pharmaceutical Company Limited | アミノフェニルプロパン酸誘導体 |
| WO2005099688A2 (en) * | 2004-04-07 | 2005-10-27 | Takeda Pharmaceutical Company Limited | Cyclic compounds |
| US20090227648A1 (en) * | 2004-04-21 | 2009-09-10 | Astrazeneca Ab | Pyrazole derivatives useful for the treatment of cancer |
| WO2005105788A1 (en) * | 2004-04-23 | 2005-11-10 | Takeda San Diego, Inc. | Indole derivatives and use thereof as kinase inhibitors |
| CA2564355C (en) * | 2004-05-07 | 2012-07-03 | Amgen Inc. | Protein kinase modulators and method of use |
| US7793137B2 (en) | 2004-10-07 | 2010-09-07 | Cisco Technology, Inc. | Redundant power and data in a wired data telecommunincations network |
| SI1771450T1 (sl) * | 2004-05-14 | 2008-06-30 | Millennium Pharm Inc | Spojine in postopki za inhibiranje mitotične progresije z inhibicijo kinaze Aurora |
| AU2005245877B2 (en) * | 2004-05-14 | 2010-06-03 | Vertex Pharmaceuticals, Incorporated | Prodrugs of pyrrolylpyrimidine ERK protein kinase inhibitors |
| US20050255485A1 (en) * | 2004-05-14 | 2005-11-17 | Livak Kenneth J | Detection of gene duplications |
| AU2012200416B2 (en) * | 2004-05-14 | 2014-07-31 | Millennium Pharmaceuticals, Inc. | "Compounds and methods for inhibiting mitotic progression by inhibition of Aurora kinase" |
| DE602005003951T4 (de) * | 2004-05-14 | 2012-10-11 | Millennium Pharmaceuticals, Inc. | Verbindungen und verfahren zur inhibierung der mitotischen progression durch hemmung von aurorakinase |
| CA2567352A1 (en) * | 2004-05-20 | 2005-12-01 | Bayer Pharmaceuticals Corporation | 5-anilino-4-heteroarylpyrazole derivatives useful for the treatment of diabetes |
| CN1973247A (zh) * | 2004-05-27 | 2007-05-30 | 纳幕尔杜邦公司 | 光聚合物保护层的显影剂 |
| TW200612948A (en) * | 2004-07-01 | 2006-05-01 | Synta Pharmaceuticals Corp | 2-substituted heteroaryl compounds |
| JP2008505907A (ja) * | 2004-07-06 | 2008-02-28 | アンジオン バイオメディカ コーポレイション | 癌治療を目的として肝細胞増殖因子およびc−met活性を調整するキナゾリンモジュレーター |
| US7550598B2 (en) * | 2004-08-18 | 2009-06-23 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
| US7285569B2 (en) | 2004-09-24 | 2007-10-23 | Hoff Hoffmann-La Roche Inc. | Tricycles, their manufacture and use as pharmaceutical agents |
| TW200624431A (en) * | 2004-09-24 | 2006-07-16 | Hoffmann La Roche | Phthalazinone derivatives, their manufacture and use as pharmaceutical agents |
| WO2006035069A1 (en) * | 2004-09-30 | 2006-04-06 | Tibotec Pharmaceuticals Ltd. | Hiv inhibiting 5-substituted pyrimidines |
| WO2006035067A2 (en) * | 2004-09-30 | 2006-04-06 | Tibotec Pharmaceuticals Ltd. | Hiv inhibiting 5-heterocyclyl pyrimidines |
| BRPI0515935B8 (pt) * | 2004-09-30 | 2021-05-25 | Janssen Sciences Ireland Uc | pirimidinas heterociclil- ou 5-carbo substituídas para inibição de hiv, e composição farmacêutica |
| US7713973B2 (en) | 2004-10-15 | 2010-05-11 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
| EP1828165B1 (en) * | 2004-10-29 | 2013-03-20 | Msd K.K. | Novel aminopyridine derivatives having aurora a selective inhibitory action |
| US7491720B2 (en) | 2004-10-29 | 2009-02-17 | Banyu Pharmaceutical Co., Ltd. | Aminopyridine derivatives having Aurora A selective inhibitory action |
| EP1809290A2 (en) | 2004-11-03 | 2007-07-25 | Vertex Pharmaceuticals Incorporated | Pyrimidine derivatives as ion channel modulators and methods of use |
| WO2006055831A2 (en) * | 2004-11-17 | 2006-05-26 | Miikana Therapeutics, Inc. | Kinase inhibitors |
| ES2380550T3 (es) | 2004-11-24 | 2012-05-16 | Rigel Pharmaceuticals, Inc. | Compuestos de espiro-2,4-pirimidindiamina y sus usos |
| US20060128710A1 (en) * | 2004-12-09 | 2006-06-15 | Chih-Hung Lee | Antagonists to the vanilloid receptor subtype 1 (VR1) and uses thereof |
| JP2008525422A (ja) * | 2004-12-23 | 2008-07-17 | ファイザー・プロダクツ・インク | 抗癌剤として有用な複素芳香族誘導体 |
| JP5208516B2 (ja) | 2004-12-30 | 2013-06-12 | エグゼリクシス, インコーポレイテッド | キナーゼモジュレーターとしてのピリミジン誘導体および使用方法 |
| TWI427077B (zh) | 2004-12-30 | 2014-02-21 | Astex Therapeutics Ltd | 吡唑化合物及其用途和含有彼之藥學組成物 |
| CA2592900A1 (en) | 2005-01-03 | 2006-07-13 | Myriad Genetics Inc. | Nitrogen containing bicyclic compounds and therapeutical use thereof |
| US8258145B2 (en) | 2005-01-03 | 2012-09-04 | Myrexis, Inc. | Method of treating brain cancer |
| NZ555947A (en) | 2005-01-19 | 2010-11-26 | Rigel Pharmaceuticals Inc | Prodrugs of 2,4-pyrimidinediamine compounds and their uses |
| US8404718B2 (en) | 2005-01-21 | 2013-03-26 | Astex Therapeutics Limited | Combinations of pyrazole kinase inhibitors |
| AR054425A1 (es) | 2005-01-21 | 2007-06-27 | Astex Therapeutics Ltd | Sales de adicion de piperidin 4-il- amida de acido 4-(2,6-dicloro-benzoilamino) 1h-pirazol-3-carboxilico. |
| WO2006081230A2 (en) * | 2005-01-26 | 2006-08-03 | Schering Corporation | 3-(indazol-5-yl)-(1,2, 4) triazine derivatives and related compounds as protein kinase inhibitors for the treatment of cancer |
| JP5139084B2 (ja) | 2005-02-04 | 2013-02-06 | アストラゼネカ アクチボラグ | キナーゼ阻害剤として有用なピラゾリルアミノピリジン誘導体 |
| SI1853602T1 (sl) * | 2005-02-16 | 2010-11-30 | Astrazeneca Ab | Kemične spojine |
| PL1853588T3 (pl) * | 2005-02-16 | 2008-11-28 | Astrazeneca Ab | Związki chemiczne |
| CA2600144A1 (en) * | 2005-03-15 | 2006-09-28 | Irm Llc | Compounds and compositions as protein kinase inhibitors |
| US20080161278A1 (en) * | 2005-03-23 | 2008-07-03 | Astrazeneca Ab | 2-Azetidinyl-4-(1H-Pyrazol-3-Ylamino) Pyrimidines as Inhibitors of Insulin-Like Growth Factor-1 Receptor Activity |
| US7297700B2 (en) | 2005-03-24 | 2007-11-20 | Renovis, Inc. | Bicycloheteroaryl compounds as P2X7 modulators and uses thereof |
| ATE404554T1 (de) * | 2005-04-05 | 2008-08-15 | Astrazeneca Ab | Pyrimidinderivate zur verwendung als antikrebsmittel |
| GB0507347D0 (en) * | 2005-04-12 | 2005-05-18 | Astrazeneca Ab | Chemical compounds |
| AU2006233537A1 (en) | 2005-04-14 | 2006-10-19 | F. Hoffmann-La Roche Ag | Aminopyrazole derivatives, their manufacture and use as pharmaceutical agents |
| CN101208093A (zh) * | 2005-04-27 | 2008-06-25 | 阿斯利康(瑞典)有限公司 | 吡唑-嘧啶衍生物在治疗疼痛中的用途 |
| ES2545382T3 (es) | 2005-04-28 | 2015-09-10 | Mitsubishi Tanabe Pharma Corporation | Derivado de cianopiridina y su uso como medicamento |
| US20080207594A1 (en) | 2005-05-04 | 2008-08-28 | Davelogen Aktiengesellschaft | Use of Gsk-3 Inhibitors for Preventing and Treating Pancreatic Autoimmune Disorders |
| US7745451B2 (en) | 2005-05-04 | 2010-06-29 | Renovis, Inc. | Tetrahydronaphthyridine and tetrahydropyrido[4,3-d]pyrimidine compounds and compositions thereof useful in the treatment of conditions associated with neurological and inflammatory disorders and dysfunctions |
| CN101218229A (zh) * | 2005-05-05 | 2008-07-09 | 阿斯利康(瑞典)有限公司 | 吡唑基-氨基取代的嘧啶及其在癌症治疗中的应用 |
| JP2008540622A (ja) * | 2005-05-16 | 2008-11-20 | アストラゼネカ アクチボラグ | 化合物 |
| MX286273B (es) | 2005-06-08 | 2011-05-04 | Rigel Pharmaceuticals Inc | Composiciones y metodos para inhibicion de la via jak. |
| US20070203161A1 (en) | 2006-02-24 | 2007-08-30 | Rigel Pharmaceuticals, Inc. | Compositions and methods for inhibition of the jak pathway |
| US8193206B2 (en) | 2005-06-14 | 2012-06-05 | Taigen Biotechnology Co., Ltd. | Pyrimidine compounds |
| KR101354114B1 (ko) | 2005-06-14 | 2014-01-24 | 타이젠 바이오테크놀러지 컴퍼니 리미티드 | 피리미딘 화합물 |
| EP1746096A1 (en) | 2005-07-15 | 2007-01-24 | 4Sc Ag | 2-Arylbenzothiazole analogues and uses thereof in the treatment of cancer |
| US7737151B2 (en) * | 2005-08-18 | 2010-06-15 | Vertex Pharmaceuticals Incorporated | Pyrazine kinase inhibitors |
| WO2007023382A2 (en) * | 2005-08-25 | 2007-03-01 | Pfizer Inc. | Pyrimidine amino pyrazole compounds, potent kinase inhibitors |
| US7678363B2 (en) | 2005-08-26 | 2010-03-16 | Braincells Inc | Methods of treating psychiatric conditions comprising administration of muscarinic agents in combination with SSRIs |
| EP2258359A3 (en) | 2005-08-26 | 2011-04-06 | Braincells, Inc. | Neurogenesis by muscarinic receptor modulation with sabcomelin |
| UA96427C2 (en) * | 2005-09-30 | 2011-11-10 | Мийкана Терапьютикс, Инк. | Substituted pyrazole compounds |
| EP1928456B1 (en) * | 2005-09-30 | 2015-04-22 | Miikana Therapeutics, Inc. | Substituted pyrazole compounds |
| US8119655B2 (en) * | 2005-10-07 | 2012-02-21 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
| WO2007047978A2 (en) | 2005-10-21 | 2007-04-26 | Braincells, Inc. | Modulation of neurogenesis by pde inhibition |
| JP2009513615A (ja) | 2005-10-28 | 2009-04-02 | アストラゼネカ アクチボラグ | 癌の治療においてチロシンキナーゼ阻害剤として使用するための4−(3−アミノピラゾール)ピリミジン誘導体 |
| AU2006308889A1 (en) | 2005-10-31 | 2007-05-10 | Braincells, Inc. | GABA receptor mediated modulation of neurogenesis |
| WO2007053345A1 (en) * | 2005-11-01 | 2007-05-10 | Array Biopharma Inc. | Glucokinase activators |
| US7528142B2 (en) * | 2005-11-03 | 2009-05-05 | Vertex Pharmaceuticals Incorporated | Aminopyrimidines useful as kinase inhibitors |
| AU2006315334B2 (en) * | 2005-11-16 | 2011-05-19 | Vertex Pharmaceuticals Incorporated | Aminopyrimidines useful as kinase inhibitors |
| US8546404B2 (en) | 2005-12-13 | 2013-10-01 | Merck Sharp & Dohme | Compounds that are ERK inhibitors |
| US7572809B2 (en) * | 2005-12-19 | 2009-08-11 | Hoffmann-La Roche Inc. | Isoquinoline aminopyrazole derivatives |
| EP1968579A1 (en) | 2005-12-30 | 2008-09-17 | Astex Therapeutics Limited | Pharmaceutical compounds |
| WO2007081978A2 (en) * | 2006-01-11 | 2007-07-19 | Angion Biomedica Corporation | Modulators of hepatocyte growth factor / c-met activity |
| JO2660B1 (en) | 2006-01-20 | 2012-06-17 | نوفارتيس ايه جي | Pi-3 inhibitors and methods of use |
| MX2008010635A (es) | 2006-02-16 | 2008-10-28 | Schering Corp | Derivados de pirrolidina como inhibidores de cinasa regulada por señales extracelulares. |
| US20100216734A1 (en) | 2006-03-08 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| PE20080145A1 (es) | 2006-03-21 | 2008-02-11 | Janssen Pharmaceutica Nv | Tetrahidro-pirimidoazepinas como moduladores de trpv1 |
| EP2004632B1 (en) | 2006-03-30 | 2014-03-12 | Janssen R&D Ireland | Hiv inhibiting 5-amido substituted pyrimidines |
| US8008481B2 (en) * | 2006-03-31 | 2011-08-30 | Ericsson Anna M | Indazole compounds |
| JP2009532440A (ja) | 2006-04-07 | 2009-09-10 | ノバルティス アクチエンゲゼルシャフト | a)ピリミジルアミノベンズアミド化合物、およびb)Thr315Ileキナーゼ阻害剤を含む、組合せ剤 |
| ZA200809493B (en) | 2006-04-14 | 2010-08-25 | Prana Biotechnology Ltd | Method of treatment of age-related macular degeneration (AMD) |
| WO2007126126A1 (ja) * | 2006-04-27 | 2007-11-08 | Banyu Pharmaceutical Co., Ltd. | オーロラa選択的阻害作用を有する新規アミノピリジン誘導体 |
| CA2651813A1 (en) | 2006-05-09 | 2007-11-22 | Braincells, Inc. | Neurogenesis by modulating angiotensin |
| WO2007134077A2 (en) | 2006-05-09 | 2007-11-22 | Braincells, Inc. | 5 ht receptor mediated neurogenesis |
| JO2969B1 (en) | 2006-06-27 | 2016-03-15 | تاكيدا فارماسويتيكال كمبني ليمتد | Welded circular compounds |
| JP5523829B2 (ja) | 2006-06-29 | 2014-06-18 | アステックス、セラピューティックス、リミテッド | 複合薬剤 |
| WO2008001101A2 (en) * | 2006-06-29 | 2008-01-03 | Astex Therapeutics Limited | Pharmaceutical combinations |
| US20090209537A1 (en) * | 2006-06-30 | 2009-08-20 | Kyowa Hakko Kirin Co., Ltd. | Aurora inhibitors |
| WO2008001070A1 (en) * | 2006-06-30 | 2008-01-03 | Astrazeneca Ab | Pyrimidine derivatives useful in the treatment of cancer |
| US8222256B2 (en) | 2006-07-05 | 2012-07-17 | Exelixis, Inc. | Methods of using IGFIR and ABL kinase modulators |
| BRPI0715160A2 (pt) | 2006-08-08 | 2013-06-11 | Sanofi Aventis | imidazolidina-2,4-dionas substituÍdas por arilamimoaril-alquil-, processo para preparÁ-las, medicamentos compeendendo estes compostos, e seu uso |
| JP2010500352A (ja) * | 2006-08-09 | 2010-01-07 | ミレニアム・ファーマシューティカルズ・インコーポレイテッド | 有糸分裂の進行を阻止するためのピリドベンゾアゼピン化合物および方法 |
| US7832809B2 (en) * | 2006-08-11 | 2010-11-16 | Schlumberger Technology Corporation | Degradation assembly shield |
| JP2008081492A (ja) | 2006-08-31 | 2008-04-10 | Banyu Pharmaceut Co Ltd | オーロラa選択的阻害作用を有する新規アミノピリジン誘導体 |
| CA2662491A1 (en) * | 2006-09-08 | 2008-03-13 | Braincells, Inc. | Combinations containing a 4-acylaminopyridine derivative |
| US20100184806A1 (en) | 2006-09-19 | 2010-07-22 | Braincells, Inc. | Modulation of neurogenesis by ppar agents |
| EP2223925A1 (en) * | 2006-10-09 | 2010-09-01 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
| SG158147A1 (en) | 2006-10-09 | 2010-01-29 | Takeda Pharmaceutical | Kinase inhibitors |
| US8883790B2 (en) | 2006-10-12 | 2014-11-11 | Astex Therapeutics Limited | Pharmaceutical combinations |
| US8916552B2 (en) | 2006-10-12 | 2014-12-23 | Astex Therapeutics Limited | Pharmaceutical combinations |
| WO2008053812A1 (en) * | 2006-10-27 | 2008-05-08 | Mitsubishi Tanabe Pharma Corporation | Cyanopyridine derivative and medicinal use thereof |
| ATE457311T1 (de) * | 2006-11-02 | 2010-02-15 | Vertex Pharma | Als inhibitoren von proteinkinasen geeignete aminopyridine und aminopyrimidine |
| CL2007003244A1 (es) | 2006-11-16 | 2008-04-04 | Millennium Pharm Inc | Compuestos derivados de pirimido[5,4-d][2]benzazepina; composicion farmaceutica que comprende a dicho compuesto; y uso del compuesto para el tratamiento del cancer. |
| NZ577768A (en) | 2006-12-19 | 2012-01-12 | Vertex Pharma | Aminopyrimidines useful as inhibitors of protein kinases |
| EA020749B1 (ru) * | 2006-12-29 | 2015-01-30 | Тиботек Фармасьютикалз Лтд. | Вич-ингибирующие 5,6-замещенные пиримидины |
| KR20090094073A (ko) * | 2006-12-29 | 2009-09-03 | 티보텍 파마슈티칼즈 리미티드 | Hiv를 억제하는 6-치환된 피리미딘 |
| EP2118087B1 (en) | 2007-02-06 | 2012-03-28 | Novartis AG | Pi 3-kinase inhibitors and methods of their use |
| EP2133095A4 (en) | 2007-03-05 | 2012-09-26 | Kyowa Hakko Kirin Co Ltd | PHARMACEUTICAL COMPOSITION |
| AU2008226461A1 (en) * | 2007-03-09 | 2008-09-18 | Vertex Pharmaceuticals Incorporated | Aminopyridines useful as inhibitors of protein kinases |
| CN101663295B (zh) * | 2007-03-09 | 2014-11-05 | 沃泰克斯药物股份有限公司 | 可用作蛋白激酶抑制剂的氨基嘧啶类化合物 |
| AU2008226466B2 (en) * | 2007-03-09 | 2013-06-13 | Vertex Pharmaceuticals Incorporated | Aminopyrimidines useful as inhibitors of protein kinases |
| MX2009010037A (es) * | 2007-03-20 | 2009-11-05 | Vertex Pharma | Aminopirimidinas utiles como inhibidores de cinasas. |
| WO2008117050A1 (en) * | 2007-03-27 | 2008-10-02 | Astrazeneca Ab | Pyrazolyl-amino-substituted pyrazines and their use for the treatment of cancer |
| JP2010523700A (ja) * | 2007-04-13 | 2010-07-15 | バーテックス ファーマシューティカルズ インコーポレイテッド | キナーゼインヒビターとして有用なアミノピリミジン |
| WO2008129255A1 (en) * | 2007-04-18 | 2008-10-30 | Astrazeneca Ab | 5-aminopyrazol-3-yl-3h-imidazo [4,5-b] pyridine derivatives and their use for the treatment of cancer |
| JP4782239B2 (ja) | 2007-04-18 | 2011-09-28 | ファイザー・プロダクツ・インク | 異常細胞増殖治療のためのスルホニルアミド誘導体 |
| WO2008137619A2 (en) | 2007-05-02 | 2008-11-13 | Vertex Pharmaceuticals Incorporated | Thiazoles and pyrazoles useful as kinase inhibitors |
| AU2008247594A1 (en) * | 2007-05-02 | 2008-11-13 | Vertex Pharmaceuticals Incorporated | Aminopyrimidines useful as kinase inhibitors |
| CA2688584A1 (en) * | 2007-05-02 | 2008-11-13 | Vertex Pharmaceuticals Incorporated | Aminopyrimidines useful as kinase inhibitors |
| UA99459C2 (en) * | 2007-05-04 | 2012-08-27 | Астразенека Аб | 9-(pyrazol-3-yl)- 9h-purine-2-amine and 3-(pyraz0l-3-yl)-3h-imidazo[4,5-b]pyridin-5-amine derivatives and their use for the treatment of cancer |
| ATE521609T1 (de) * | 2007-05-04 | 2011-09-15 | Astrazeneca Ab | Aminothiazolylpyrimidinderivate und ihre verwendung bei der behandlung von krebs |
| WO2008147626A2 (en) * | 2007-05-24 | 2008-12-04 | Vertex Pharmaceuticals Incorporated | Thiazoles and pyrazoles useful as kinase inhibitors |
| KR101294731B1 (ko) * | 2007-06-04 | 2013-08-16 | 삼성디스플레이 주식회사 | 어레이 기판, 이를 갖는 표시패널 및 이의 제조방법 |
| CA2683152A1 (en) * | 2007-06-11 | 2008-12-18 | Miikana Therapeutics, Inc. | Substituted pyrazole compounds |
| JP2010532756A (ja) * | 2007-07-06 | 2010-10-14 | オーエスアイ・ファーマスーティカルズ・インコーポレーテッド | mTORC1及びmTORC2の両方の阻害剤を含む組み合わせ抗癌療法 |
| WO2009007753A2 (en) * | 2007-07-11 | 2009-01-15 | Astrazeneca Ab | 4- (3-aminopyrazole) -pyrimidine derivativee and their use as tyrosine kinase inhibitors for the treatment of cancer |
| KR20100038108A (ko) * | 2007-07-25 | 2010-04-12 | 브리스톨-마이어스 스큅 컴퍼니 | 트리아진 키나제 억제제 |
| WO2009013545A2 (en) * | 2007-07-26 | 2009-01-29 | Astrazeneca Ab | Chemical compounds |
| TW200906818A (en) * | 2007-07-31 | 2009-02-16 | Astrazeneca Ab | Chemical compounds |
| NZ582879A (en) * | 2007-07-31 | 2012-03-30 | Vertex Pharma | Process for preparing 5-fluoro-1h-pyrazolo [3, 4-b] pyridin-3-amine and derivatives thereof |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| WO2009027736A2 (en) * | 2007-08-27 | 2009-03-05 | Astrazeneca Ab | 2,4 diaminopyrimid'lnes for the treatment of myeloproliferative disorders and cancer |
| SI2209778T1 (sl) | 2007-09-21 | 2012-12-31 | Array Biopharma, Inc. | Piridin-2-il-amino-I, 2,4-tiadiazol derivati kot aktivatorji glukokinaze za zdravljenje sladkorne bolezni |
| NZ584471A (en) | 2007-10-11 | 2012-01-12 | Glaxosmithkline Llc | Triazine cyclohexane carboxamide compounds and their use |
| CL2008003749A1 (es) | 2007-12-17 | 2010-01-15 | Janssen Pharmaceutica Nv | Compuestos derivados de imidazol, oxazol, y tiazol pirimidina, moduladores de trpv1, proceso de preparacion, composicion farmaceutica y su uso en el tratamiento de enfermedades, trastornos o condicion de dolor, prurito, artritis, tos, asma, trastorno del oido interno y enfermedad inflamatoria intestinal, entre otras. |
| US20090270418A1 (en) * | 2008-01-09 | 2009-10-29 | Marianne Sloss | Pyrazole pyrazine amine compounds as kinase inhibitors, compositions thereof and methods of treatment therewith |
| WO2009097995A1 (de) * | 2008-02-07 | 2009-08-13 | Sanofi-Aventis | Neue phenyl-substituierte imidazolidine, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| WO2009105500A1 (en) * | 2008-02-21 | 2009-08-27 | Schering Corporation | Compounds that are erk inhibitors |
| AU2009216062B2 (en) | 2008-02-22 | 2013-02-07 | Msd K.K. | Novel aminopyridine derivatives having Aurora A selective inhibitory action |
| SI2268635T1 (sl) | 2008-04-21 | 2015-10-30 | Taigen Biotechnology Co., Ltd. | Heterociklične spojine |
| US8844033B2 (en) | 2008-05-27 | 2014-09-23 | The Trustees Of Columbia University In The City Of New York | Systems, methods, and media for detecting network anomalies using a trained probabilistic model |
| AR072085A1 (es) * | 2008-06-11 | 2010-08-04 | Astrazeneca Ab | Compuestos triciclicos, metodos para su preparacion, composicion farma-ceutica que los comprende y su uso en el tratamiento de enfermedades me-diadas por la actividad de las proteinas quinasas |
| WO2010003624A2 (en) | 2008-07-09 | 2010-01-14 | Sanofi-Aventis | Heterocyclic compounds, processes for their preparation, medicaments comprising these compounds, and the use thereof |
| KR20110046514A (ko) * | 2008-07-31 | 2011-05-04 | 제넨테크, 인크. | 피리미딘 화합물, 조성물 및 사용 방법 |
| MX2011002312A (es) * | 2008-09-03 | 2011-04-26 | Vertex Pharma | Co-cristales y formulaciones farmaceuticas que comprenden los mismos. |
| CN105574346A (zh) * | 2008-09-05 | 2016-05-11 | 新基阿维罗米克斯研究公司 | 多肽偶联物与不可逆抑制剂的设计方法和检测方法 |
| CN104230901A (zh) * | 2008-09-15 | 2014-12-24 | 加利福尼亚大学董事会 | 用于调节ire1、src和abl活性的方法和组合物 |
| TW201018693A (en) * | 2008-09-30 | 2010-05-16 | Astrazeneca Ab | Chemical compounds 496-1p |
| US8759362B2 (en) * | 2008-10-24 | 2014-06-24 | Purdue Pharma L.P. | Bicycloheteroaryl compounds and their use as TRPV1 ligands |
| WO2010056758A1 (en) * | 2008-11-12 | 2010-05-20 | Yangbo Feng | Quinazoline derivatives as kinase inhibitors |
| US9023834B2 (en) | 2008-11-13 | 2015-05-05 | Taigen Biotechnology Co., Ltd. | Lyophilization formulation |
| WO2010068601A1 (en) | 2008-12-08 | 2010-06-17 | Sanofi-Aventis | A crystalline heteroaromatic fluoroglycoside hydrate, processes for making, methods of use and pharmaceutical compositions thereof |
| PA8851101A1 (es) | 2008-12-16 | 2010-07-27 | Lilly Co Eli | Compuesto amino pirazol |
| ES2422263T3 (es) | 2008-12-19 | 2013-09-10 | Nerviano Medical Sciences Srl | Pirazoles bicíclicos como inhibidores de la proteinquinasa |
| CN102264368B (zh) | 2008-12-22 | 2014-09-10 | 米伦纽姆医药公司 | 极光激酶抑制剂与抗cd20抗体的组合 |
| WO2010072155A1 (zh) * | 2008-12-26 | 2010-07-01 | 复旦大学 | 一种嘧啶类衍生物及其制备方法和用途 |
| WO2010099217A1 (en) | 2009-02-25 | 2010-09-02 | Braincells, Inc. | Modulation of neurogenesis using d-cycloserine combinations |
| PL2401267T3 (pl) | 2009-02-27 | 2014-06-30 | Ambit Biosciences Corp | Pochodne chinazoliny modulujące kinazę JAK i ich zastosowanie w metodach |
| CA2660962A1 (en) | 2009-03-31 | 2010-09-30 | Astellas Pharma Inc. | Novel pharmaceutical composition for treatment of schizophrenia |
| US8399663B2 (en) | 2009-04-03 | 2013-03-19 | Astellas Pharma Inc. | Salt of 1,3,5-triazine-2,4,6-triamine derivative |
| JO3635B1 (ar) | 2009-05-18 | 2020-08-27 | Millennium Pharm Inc | مركبات صيدلانية صلبة وطرق لانتاجها |
| CN102573485B (zh) * | 2009-06-08 | 2014-11-26 | 加利福尼亚资本权益有限责任公司 | 三嗪衍生物及其治疗应用 |
| US20120172361A1 (en) * | 2009-06-08 | 2012-07-05 | California Capital Equity, Llc | Triazine derivatives and their therapeutical applications |
| JP2012529517A (ja) * | 2009-06-09 | 2012-11-22 | アブラクシス バイオサイエンス リミテッド ライアビリティー カンパニー | ベンジル置換トリアジン誘導体類及びそれらの治療応用 |
| BRPI1011527A2 (pt) * | 2009-06-09 | 2016-07-26 | California Capital Equity Llc | derivados de triazina substituídos com ureidofenil e suas aplicações terapêuticas. |
| KR20120026613A (ko) * | 2009-06-09 | 2012-03-19 | 아브락시스 바이오사이언스, 엘엘씨 | 스티릴-트리아진 유도체와 이들의 치료적 용도 |
| KR101457027B1 (ko) | 2009-06-09 | 2014-10-31 | 캘리포니아 캐피탈 에쿼티, 엘엘씨 | 트리아진 유도체와 이들의 치료적 용도 |
| US20120172384A1 (en) * | 2009-06-18 | 2012-07-05 | Mihiro Sunose | Heterocyclylaminopyrimidines as kinase inhibitors |
| US8637525B2 (en) | 2009-07-31 | 2014-01-28 | Bristol-Myers Squibb Company | Compounds for the reduction of beta-amyloid production |
| TWI468402B (zh) * | 2009-07-31 | 2015-01-11 | 必治妥美雅史谷比公司 | 降低β-類澱粉生成之化合物 |
| ES2443016T3 (es) | 2009-08-26 | 2014-02-17 | Sanofi | Nuevos hidratos cristalinos de fluoroglicósidos heteroaromáticos, productos farmacéuticos que comprenden estos compuestos, y su empleo |
| NZ598705A (en) | 2009-09-16 | 2014-06-27 | Celgene Avilomics Res Inc | Protein kinase conjugates and inhibitors |
| WO2011060311A2 (en) * | 2009-11-13 | 2011-05-19 | Intuitive Surgical Operations, Inc. | End effector with redundant closing mechanisms |
| EP2519517B1 (en) | 2009-12-29 | 2015-03-25 | Dana-Farber Cancer Institute, Inc. | Type ii raf kinase inhibitors |
| JP2013516422A (ja) | 2009-12-30 | 2013-05-13 | アビラ セラピューティクス, インコーポレイテッド | タンパク質のリガンド−指向性共有的修飾 |
| SA111320200B1 (ar) * | 2010-02-17 | 2014-02-16 | ديبيوفارم اس ايه | مركبات ثنائية الحلقة واستخداماتها كمثبطات c-src/jak مزدوجة |
| CN104031049A (zh) | 2010-02-19 | 2014-09-10 | 米伦纽姆医药公司 | 极光激酶抑制剂的结晶形式 |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2571359A4 (en) * | 2010-05-20 | 2013-10-23 | Merck Sharp & Dohme | NOVEL PROLYLCARBOXYPEPTIDASE HEMMER |
| CN103003264B (zh) | 2010-05-21 | 2014-08-06 | 切米利亚股份公司 | 嘧啶衍生物 |
| EP3075730B1 (en) | 2010-06-04 | 2018-10-24 | Genentech, Inc. | Aminopyrimidine derivatives as lrrk2 modulators |
| US8933024B2 (en) | 2010-06-18 | 2015-01-13 | Sanofi | Azolopyridin-3-one derivatives as inhibitors of lipases and phospholipases |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| MX341732B (es) | 2010-07-29 | 2016-08-30 | Oryzon Genomics S A * | Inhibidores de la demetilasa lsd1 basados en arilciclopropilamina y sus usos médicos. |
| WO2012030910A1 (en) * | 2010-09-01 | 2012-03-08 | Ambit Biosciences Corporation | 2-cycloquinazoline derivatives and methods of use thereof |
| ES2581840T3 (es) | 2010-09-01 | 2016-09-07 | Ambit Biosciences Corporation | Pirazolilaminoquinazolina ópticamente activa y composiciones farmacéuticas y métodos de uso de la misma |
| CN103298805A (zh) * | 2010-09-01 | 2013-09-11 | 埃姆比特生物科学公司 | 喹唑啉化合物及其使用方法 |
| EP2611794A1 (en) * | 2010-09-01 | 2013-07-10 | Ambit Biosciences Corporation | 4-azolylaminoquinazoline derivatives and methods of use thereof |
| WO2012030918A1 (en) * | 2010-09-01 | 2012-03-08 | Ambit Biosciences Corporation | Adenosine a3 receptor modulating compounds and methods of use thereof |
| WO2012030944A2 (en) * | 2010-09-01 | 2012-03-08 | Ambit Biosciences Corporation | Quinoline and isoquinoline compounds and methods of use thereof |
| EP2611792B1 (en) * | 2010-09-01 | 2017-02-01 | Ambit Biosciences Corporation | Hydrobromide salts of a pyrazolylaminoquinazoline |
| WO2012059932A1 (en) | 2010-11-01 | 2012-05-10 | Aurigene Discovery Technologies Limited | 2, 4 -diaminopyrimidine derivatives as protein kinase inhibitors |
| ES2746134T3 (es) | 2010-11-10 | 2020-03-04 | Genentech Inc | Derivados de pirazol aminopirimidina como moduladores de LRRK2 |
| EP2683702B1 (de) | 2011-03-08 | 2014-12-24 | Sanofi | Neue substituierte phenyl-oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| WO2012120055A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2683698B1 (de) | 2011-03-08 | 2017-10-04 | Sanofi | Mit adamantan- oder noradamantan substituierte benzyl-oxathiazinderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| US8828994B2 (en) | 2011-03-08 | 2014-09-09 | Sanofi | Di- and tri-substituted oxathiazine derivatives, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
| US8895547B2 (en) | 2011-03-08 | 2014-11-25 | Sanofi | Substituted phenyl-oxathiazine derivatives, method for producing them, drugs containing said compounds and the use thereof |
| EP2766349B1 (de) | 2011-03-08 | 2016-06-01 | Sanofi | Mit carbozyklen oder heterozyklen substituierte oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2683701B1 (de) | 2011-03-08 | 2014-12-24 | Sanofi | Mit benzyl- oder heteromethylengruppen substituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| WO2012120053A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Verzweigte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| US8871758B2 (en) | 2011-03-08 | 2014-10-28 | Sanofi | Tetrasubstituted oxathiazine derivatives, method for producing them, their use as medicine and drug containing said derivatives and the use thereof |
| AU2012230229A1 (en) | 2011-03-24 | 2013-10-10 | Noviga Research Ab | Novel pyrimidine derivatives |
| WO2013026914A1 (en) * | 2011-08-25 | 2013-02-28 | F. Hoffmann-La Roche Ag | Serine/threonine pak1 inhibitors |
| WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| KR20140059246A (ko) * | 2011-09-22 | 2014-05-15 | 화이자 인코포레이티드 | 피롤로피리미딘 및 퓨린 유도체 |
| KR20140069235A (ko) | 2011-09-27 | 2014-06-09 | 노파르티스 아게 | 돌연변이체 idh의 억제제로서의 3-피리미딘-4-일-옥사졸리딘-2-온 |
| WO2013045413A1 (en) | 2011-09-27 | 2013-04-04 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| JP6106685B2 (ja) | 2011-11-17 | 2017-04-05 | ダナ−ファーバー キャンサー インスティテュート, インコーポレイテッド | C−jun−n−末端キナーゼ(jnk)の阻害剤 |
| CN104011050A (zh) | 2011-12-22 | 2014-08-27 | 霍夫曼-拉罗奇有限公司 | 作为丝氨酸/苏氨酸激酶抑制剂的2,4-二氨基-嘧啶衍生物 |
| MX2014009933A (es) * | 2012-02-17 | 2015-12-16 | Abbvie Inc | Diaminopirimidinas utiles como inhibidores del virus sincitial respiratorio humano (rsv). |
| UY34632A (es) | 2012-02-24 | 2013-05-31 | Novartis Ag | Compuestos de oxazolidin- 2- ona y usos de los mismos |
| TWI485146B (zh) * | 2012-02-29 | 2015-05-21 | Taiho Pharmaceutical Co Ltd | Novel piperidine compounds or salts thereof |
| CN104302640A (zh) | 2012-03-16 | 2015-01-21 | 埃克希金医药品有限公司 | 3,5-二氨基吡唑激酶抑制剂 |
| US20130303519A1 (en) | 2012-03-20 | 2013-11-14 | Millennium Pharmaceuticals, Inc. | Methods of treating cancer using aurora kinase inhibitors |
| IN2014KN02601A (OSRAM) | 2012-04-24 | 2015-05-08 | Vertex Pharma | |
| EP2855451B1 (en) * | 2012-05-24 | 2017-10-04 | Cellzome Limited | Heterocyclyl pyrimidine analogues as tyk2 inhibitors |
| EP2872161B1 (en) | 2012-06-26 | 2020-12-16 | Del Mar Pharmaceuticals | Dianhydrogalactitol for use in treating tyrosine-kinase-inhibitor-resistant malignancies in patients with genetic polymorphisms or ahi1 dysregulations or mutations |
| US9216991B2 (en) * | 2012-07-10 | 2015-12-22 | Ares Trading S.A. | Pyrimidine pyrazolyl derivatives |
| PT2898886T (pt) * | 2012-09-19 | 2017-03-23 | Taiho Pharmaceutical Co Ltd | Composição farmacêutica para administração oral apresentando uma melhor eluição e/ou uma melhor capacidade de absorção |
| US9296733B2 (en) | 2012-11-12 | 2016-03-29 | Novartis Ag | Oxazolidin-2-one-pyrimidine derivative and use thereof for the treatment of conditions, diseases and disorders dependent upon PI3 kinases |
| CN103202843B (zh) * | 2012-12-31 | 2015-04-29 | 刘强 | 一种嘧啶衍生物在制备预防和/或治疗和/或辅助治疗癌症的药物中的用途 |
| CN103191120B (zh) * | 2012-12-31 | 2015-11-25 | 刘强 | 一种嘧啶衍生物在制备预防和/或治疗和/或辅助治疗肿瘤的药物中的用途 |
| CN103059002B (zh) * | 2012-12-31 | 2015-04-22 | 中山大学 | 具有Aurora激酶抑制活性的嘧啶衍生物及其制备方法以及应用 |
| CN103910716A (zh) * | 2013-01-07 | 2014-07-09 | 华东理工大学 | 2,4-二取代-环烷基[d]嘧啶类化合物及其用途 |
| SMT201900107T1 (it) | 2013-03-12 | 2019-02-28 | Vertex Pharma | Inibitori della dna-pk |
| KR20150131224A (ko) | 2013-03-14 | 2015-11-24 | 노파르티스 아게 | 돌연변이 idh의 억제제로서의 3-피리미딘-4-일-옥사졸리딘-2-온 |
| EP3521284B1 (en) | 2013-03-15 | 2020-12-02 | The Trustees of Columbia University in the City of New York | Pyrazine compounds as map kinase modulators and uses thereof |
| US9724354B2 (en) | 2013-03-22 | 2017-08-08 | Millennium Pharmaceuticals, Inc. | Combination of catalytic mTORC1/2 inhibitors and selective inhibitors of Aurora A kinase |
| WO2015003355A2 (en) * | 2013-07-11 | 2015-01-15 | Agios Pharmaceuticals, Inc. | Therapeutically active compounds and their methods of use |
| AU2014293013A1 (en) | 2013-07-26 | 2016-03-17 | Race Oncology Ltd. | Combinatorial methods to improve the therapeutic benefit of bisantrene |
| WO2015028848A1 (en) * | 2013-09-02 | 2015-03-05 | Piramal Enterprises Limited | Bicyclic heterocyclic compounds as multi-kinase inhibitors |
| NZ631142A (en) | 2013-09-18 | 2016-03-31 | Axikin Pharmaceuticals Inc | Pharmaceutically acceptable salts of 3,5-diaminopyrazole kinase inhibitors |
| PL3424920T3 (pl) | 2013-10-17 | 2020-11-16 | Vertex Pharmaceuticals Incorporated | Kokryształy (S)-N-metylo-8-(1-((2'-metylo-4’,6'-dideutero-[4,5'-bipirymidyn]-6-ylo)amino)propan-2-ylo)chinolino-4-karboksyamidu i ich deuterowane pochodne jako inhibitory DNA-PK |
| AU2014337122B2 (en) | 2013-10-18 | 2019-01-03 | Dana-Farber Cancer Institute, Inc. | Heteroaromatic compounds useful for the treatment of proliferative diseases |
| AU2014337044A1 (en) | 2013-10-18 | 2016-05-05 | Dana-Farber Cancer Institute, Inc. | Polycyclic inhibitors of cyclin-dependent kinase 7 (CDK7) |
| CN109045032A (zh) | 2014-01-01 | 2018-12-21 | 麦迪威森技术有限责任公司 | 氨基吡啶类化合物和使用方法 |
| US10258585B2 (en) | 2014-03-13 | 2019-04-16 | Neuroderm, Ltd. | DOPA decarboxylase inhibitor compositions |
| CN106413754B (zh) | 2014-03-13 | 2019-11-29 | 纽罗德姆有限公司 | 多巴脱羧酶抑制剂组合物 |
| MX2016012574A (es) | 2014-03-28 | 2017-09-26 | Calitor Sciences Llc | Compuestos heteroarilo sustituidos y metodos de uso. |
| HUE052099T2 (hu) | 2014-04-04 | 2021-04-28 | Iomet Pharma Ltd | Indol származékok felhasználásra az orvostudományban |
| WO2015155738A2 (en) | 2014-04-09 | 2015-10-15 | Christopher Rudd | Use of gsk-3 inhibitors or activators which modulate pd-1 or t-bet expression to modulate t cell immunity |
| CN105367555B (zh) * | 2014-08-07 | 2019-06-25 | 广东东阳光药业有限公司 | 取代的杂芳基化合物及其组合物和用途 |
| KR102073854B1 (ko) | 2014-10-13 | 2020-02-05 | 주식회사유한양행 | Egfr 돌연변이 키나아제 활성을 조절하기 위한 화합물 및 조성물 |
| JP6854762B2 (ja) | 2014-12-23 | 2021-04-07 | ダナ−ファーバー キャンサー インスティテュート, インコーポレイテッド | サイクリン依存性キナーゼ7(cdk7)の阻害剤 |
| MY191736A (en) | 2014-12-23 | 2022-07-13 | Axikin Pharmaceuticals Inc | 3,5-diaminopyrazole kinase inhibitors |
| US10227343B2 (en) * | 2015-01-30 | 2019-03-12 | Vanderbilt University | Isoquiniline and napthalene-substituted compounds as mGluR4 allosteric potentiators, compositions, and methods of treating neurological dysfunction |
| AU2016243529B2 (en) | 2015-03-27 | 2021-03-25 | Dana-Farber Cancer Institute, Inc. | Inhibitors of cyclin-dependent kinases |
| AU2016247858B2 (en) | 2015-04-17 | 2020-10-15 | Ludwig Institute For Cancer Research Ltd. | PLK4 inhibitors |
| ES2924698T3 (es) | 2015-05-28 | 2022-10-10 | Theravance Biopharma R&D Ip Llc | Proceso e intermedios para la preparación de compuestos de naftiridina como inhibidores de quinasa JAK |
| JP2018135268A (ja) * | 2015-06-05 | 2018-08-30 | 大日本住友製薬株式会社 | 新規ヘテロアリールアミノ−3−ピラゾール誘導体およびその薬理学上許容される塩 |
| JP2018524292A (ja) | 2015-07-21 | 2018-08-30 | ミレニアム ファーマシューティカルズ, インコーポレイテッドMillennium Pharmaceuticals, Inc. | オーロラキナーゼインヒビターと化学療法剤の投与 |
| JP7028766B2 (ja) | 2015-09-09 | 2022-03-02 | ダナ-ファーバー キャンサー インスティテュート, インコーポレイテッド | サイクリン依存性キナーゼの阻害剤 |
| EP3347097B1 (en) | 2015-09-11 | 2021-02-24 | Sunshine Lake Pharma Co., Ltd. | Substituted aminopyrimidine derivatives as modulators of the kinases jak, flt3 and aurora |
| KR102488323B1 (ko) | 2015-12-10 | 2023-01-12 | 피티씨 테라퓨틱스, 인크. | 헌팅턴병 치료 또는 개선을 위한 조성물 |
| CN105399695B (zh) * | 2015-12-11 | 2019-04-19 | 浙江大学 | 三嗪类化合物及其制备方法和用途 |
| CN105384702B (zh) * | 2015-12-11 | 2018-04-10 | 浙江大学 | 三取代均三嗪类化合物及其制备方法 |
| CN105503754B (zh) * | 2015-12-11 | 2017-11-17 | 浙江大学 | 2‑氨基‑4‑苄基‑6‑吗啉‑1,3,5‑三嗪及其制备和应用 |
| US10894784B2 (en) | 2015-12-18 | 2021-01-19 | Bayer Pharma Aktiengesellschaft | Heteroarylbenzimidazole compounds |
| EP3430000B1 (en) | 2016-03-14 | 2022-12-28 | Afferent Pharmaceuticals Inc. | Pyrimidines and variants thereof, and uses therefor |
| WO2017165255A1 (en) * | 2016-03-25 | 2017-09-28 | Afferent Pharmaceuticals Inc. | Pyrimidines and variants thereof, and uses therefor |
| TWI726094B (zh) | 2016-04-28 | 2021-05-01 | 美商施萬生物製藥研發Ip有限責任公司 | 作為jak激酶抑制劑之嘧啶化合物 |
| WO2017207534A1 (en) | 2016-06-03 | 2017-12-07 | Bayer Pharma Aktiengesellschaft | Substituted heteroarylbenzimidazole compounds |
| MX394860B (es) | 2016-09-27 | 2025-03-24 | Vertex Pharma | Metodo para tratar cancer usando una combinacion de agentes que dañan adn e inhibidores de proteina cinasa dependiente de adn (adn-pk). |
| US10858319B2 (en) | 2016-10-03 | 2020-12-08 | Iomet Pharma Ltd. | Indole derivatives for use in medicine |
| WO2018089546A1 (en) * | 2016-11-08 | 2018-05-17 | Vanderbilt University | Isoquinoline ether compounds as mglur4 allosteric potentiators, compositions, and methods of treating neurological dysfunction |
| CN108239071B (zh) * | 2016-12-27 | 2020-12-04 | 沈阳药科大学 | 酰胺及硫代酰胺类衍生物及其制备方法和应用 |
| FR3064275B1 (fr) | 2017-03-21 | 2019-06-07 | Arkema France | Procede de chauffage et/ou climatisation d'un vehicule |
| UA126679C2 (uk) | 2017-05-30 | 2023-01-11 | Басф Се | Піридинові та піразинові сполуки |
| KR20200033249A (ko) | 2017-06-05 | 2020-03-27 | 피티씨 테라퓨틱스, 인크. | 헌팅턴병 치료 화합물 |
| MX2019015580A (es) | 2017-06-28 | 2020-07-28 | Ptc Therapeutics Inc | Metodos para tratar la enfermedad de huntington. |
| MX2019015578A (es) | 2017-06-28 | 2020-07-28 | Ptc Therapeutics Inc | Metodos para tratar la enfermedad de huntington. |
| US10329282B2 (en) | 2017-06-30 | 2019-06-25 | Beijing Tide Pharmaceutical Co., Ltd. | Rho-associated protein kinase inhibitor, pharmaceutical composition comprising the same, as well as preparation method and use thereof |
| WO2019000683A1 (zh) | 2017-06-30 | 2019-01-03 | 北京泰德制药股份有限公司 | Rho相关蛋白激酶抑制剂、包含其的药物组合物及其制备方法和用途 |
| CN111217797B (zh) | 2017-06-30 | 2021-02-05 | 北京泰德制药股份有限公司 | Rho相关蛋白激酶抑制剂、包含其的药物组合物及其制备方法和用途 |
| EP3676264A1 (en) * | 2017-08-28 | 2020-07-08 | Acurastem Inc. | Pikfyve kinase inhibitors |
| US11440904B2 (en) * | 2017-08-28 | 2022-09-13 | Zhihong Chen | Substituted pyrimidines, pharmaceutical compositions and therapeutic methods thereof |
| SG11202001706RA (en) | 2017-10-27 | 2020-03-30 | Theravance Biopharma R&D Ip Llc | Pyrimidine compound as jak kinase inhibitor |
| US20200399250A1 (en) * | 2017-11-23 | 2020-12-24 | Biomed X Gmbh | Pyrimidine Derivatives as Tropomyosin Receptor Kinase A (TRKA) Inhibitors |
| EP3720560A4 (en) * | 2017-12-06 | 2022-01-05 | Ludwig Institute for Cancer Research Ltd | METHOD OF TREATMENT OF CANCER WITH PLK4 INHIBITORS |
| KR20200143376A (ko) | 2018-03-13 | 2020-12-23 | 샤이어 휴먼 지네틱 테라피즈 인크. | 혈장 칼리크레인 억제제로서의 치환된 이미다조피리딘 및 이의 용도 |
| US12103926B2 (en) | 2018-03-27 | 2024-10-01 | Ptc Therapeutics, Inc. | Compounds for treating huntington's disease |
| EP3810132A4 (en) | 2018-06-25 | 2022-06-22 | Dana-Farber Cancer Institute, Inc. | TAIRE FAMILY KINASE INHIBITORS AND RELATED USES |
| AU2019294478B2 (en) | 2018-06-27 | 2023-03-23 | Ptc Therapeutics, Inc. | Heterocyclic and heteroaryl compounds for treating Huntington's disease |
| US11685746B2 (en) | 2018-06-27 | 2023-06-27 | Ptc Therapeutics, Inc. | Heteroaryl compounds for treating Huntington's disease |
| WO2020005877A1 (en) | 2018-06-27 | 2020-01-02 | Ptc Therapeutics, Inc. | Heteroaryl compounds for treating huntington's disease |
| US20230043863A1 (en) * | 2018-11-30 | 2023-02-09 | Jiangsu Hansoh Pharmaceutical Group Co., Ltd. | Heteroaromatic derivatives for use as regulator, preparation method therefor and use thereof |
| AU2019413694B2 (en) | 2018-12-28 | 2025-03-20 | Dana-Farber Cancer Institute, Inc. | Inhibitors of cyclin-dependent kinase 7 and uses thereof |
| EP3959213B1 (en) | 2019-04-24 | 2024-06-05 | Theravance Biopharma R&D IP, LLC | Pyrimidine jak inhibitors for the treatment of skin diseases |
| CA3135383A1 (en) | 2019-04-24 | 2020-10-29 | Theravance Biopharma R&D Ip, Llc | Ester and carbonate pyrimidine compounds as jak kinase inhibitors |
| US12428395B2 (en) | 2019-08-01 | 2025-09-30 | Sperogenix Therapeutics Limited | Heterocyclic compounds as kinase inhibitor and uses thereof |
| CN114667289B (zh) | 2019-09-18 | 2025-08-26 | 武田药品工业有限公司 | 杂芳基血浆激肽释放酶抑制剂 |
| US11787796B2 (en) | 2019-09-18 | 2023-10-17 | Takeda Pharmaceutical Company Limited | Plasma Kallikrein inhibitors and uses thereof |
| CN110483493A (zh) * | 2019-09-19 | 2019-11-22 | 广东工业大学 | 一种二唑类衍生物及其制备方法和应用 |
| AU2021207804A1 (en) | 2020-01-13 | 2022-09-01 | Verge Analytics, Inc. | Substituted pyrazolo-pyrimidines and uses thereof |
| US11213502B1 (en) | 2020-11-17 | 2022-01-04 | Neuroderm, Ltd. | Method for treatment of parkinson's disease |
| US11331293B1 (en) | 2020-11-17 | 2022-05-17 | Neuroderm, Ltd. | Method for treatment of Parkinson's disease |
| US11844754B2 (en) | 2020-11-17 | 2023-12-19 | Neuroderm, Ltd. | Methods for treatment of Parkinson's disease |
| TW202237119A (zh) | 2020-12-10 | 2022-10-01 | 美商住友製藥腫瘤公司 | Alk﹘5抑制劑和彼之用途 |
| JP2024510504A (ja) * | 2021-03-17 | 2024-03-07 | 武田薬品工業株式会社 | 血漿カリクレインの多環式インヒビター |
| AU2022243600A1 (en) * | 2021-03-26 | 2023-10-12 | Sumitomo Pharma Oncology, Inc. | Alk-5 inhibitors and uses thereof |
| US20240270722A1 (en) | 2021-05-11 | 2024-08-15 | Oric Pharmaceuticals, Inc. | Polo like kinase 4 inhibitors |
| TW202317574A (zh) | 2021-06-28 | 2023-05-01 | 美商纜圖藥品公司 | Cdk2抑制劑 |
| KR102692529B1 (ko) * | 2021-07-01 | 2024-08-08 | 한국원자력의학원 | Mastl-pp2a를 표적화하는 암의 예방 또는 치료용 약학적 조성물 |
| CN116354938B (zh) * | 2021-12-28 | 2024-02-20 | 沈阳药科大学 | 一类喹唑啉衍生物与其类似物的制备方法及应用 |
| CN114276302B (zh) * | 2022-01-11 | 2023-07-25 | 山东百启生物医药有限公司 | 一种制备2,4-二氨基喹唑啉衍生物的方法 |
| CN116813595B (zh) * | 2022-03-28 | 2025-07-18 | 上海医药工业研究院有限公司 | 喹唑啉类衍生物、其制备方法、药物组合物及应用 |
| WO2024003773A1 (en) | 2022-07-01 | 2024-01-04 | Pfizer Inc. | 2,7-naphthyridine compounds as mastl inhibitors |
| CN117736198A (zh) * | 2022-09-21 | 2024-03-22 | 科辉智药生物科技(深圳)有限公司 | 大环含氮冠醚化合物及其作为蛋白激酶抑制剂的应用 |
| CN115403568B (zh) * | 2022-09-21 | 2023-09-29 | 中山大学 | 一种喹唑啉类Aurora A共价抑制剂及其制备方法和应用 |
| WO2024178335A2 (en) * | 2023-02-23 | 2024-08-29 | Accutar Biotechnology, Inc. | Novel macrocyclic aminopyrazole compounds as cdk2 inhibitors |
| US12161612B2 (en) | 2023-04-14 | 2024-12-10 | Neuroderm, Ltd. | Methods and compositions for reducing symptoms of Parkinson's disease |
Family Cites Families (102)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3133081A (en) | 1964-05-12 | J-aminoindazole derivatives | ||
| US18436A (en) * | 1857-10-20 | And saml | ||
| US2585906A (en) | 1952-02-12 | Quaternary salts of pyrimdjines | ||
| US3935183A (en) | 1970-01-26 | 1976-01-27 | Imperial Chemical Industries Limited | Indazole-azo phenyl compounds |
| BE754242A (fr) | 1970-07-15 | 1971-02-01 | Geigy Ag J R | Diamino-s-triazines et dinitro-s-triazines |
| US3755332A (en) * | 1971-07-01 | 1973-08-28 | Ciba Geigy Corp | Substituted 4 indazolaminoquinolines |
| US3998951A (en) | 1974-03-13 | 1976-12-21 | Fmc Corporation | Substituted 2-arylquinazolines as fungicides |
| DE2458965C3 (de) | 1974-12-13 | 1979-10-11 | Bayer Ag, 5090 Leverkusen | 3-Amino-indazol-N-carbonsäure-Derivate, Verfahren zu ihrer Herstellung sowie sie enthaltende Arzneimittel |
| MA18829A1 (fr) | 1979-05-18 | 1980-12-31 | Ciba Geigy Ag | Derives de la pyrimidine,procedes pour leur preparation,compositions pharmaceutiques contenant ces composes et leur utilisation therapeutique |
| DOP1981004033A (es) * | 1980-12-23 | 1990-12-29 | Ciba Geigy Ag | Procedimiento para proteger plantas de cultivo de la accion fitotoxica de herbicidas. |
| SE8102193L (sv) | 1981-04-06 | 1982-10-07 | Pharmacia Ab | Terapeutiskt aktiv organisk forening och dess anvendning |
| SE8102194L (sv) | 1981-04-06 | 1982-10-07 | Pharmacia Ab | Terapeutiskt aktiv organisk forening och farmaceutisk beredning innehallande denna |
| JPS58124773A (ja) | 1982-01-20 | 1983-07-25 | Mitsui Toatsu Chem Inc | 5−メチルチオピリミジン誘導体とその製造法と農園芸用殺菌剤 |
| EP0136976A3 (de) | 1983-08-23 | 1985-05-15 | Ciba-Geigy Ag | Verwendung von Phenylpyrimidinen als Pflanzenregulatoren |
| DE3725638A1 (de) | 1987-08-03 | 1989-02-16 | Bayer Ag | Neue aryloxy (bzw. thio)aminopyrimidine |
| JPH0532662A (ja) | 1990-11-09 | 1993-02-09 | Nissan Chem Ind Ltd | 置換ピラゾール誘導体および農園芸用殺菌剤 |
| US5714493A (en) * | 1991-05-10 | 1998-02-03 | Rhone-Poulenc Rorer Pharmaceuticals, Inc. | Aryl and heteroaryl quinazoline compounds which inhibit CSF-1R receptor tyrosine kinase |
| US5710158A (en) | 1991-05-10 | 1998-01-20 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Aryl and heteroaryl quinazoline compounds which inhibit EGF and/or PDGF receptor tyrosine kinase |
| US5597920A (en) | 1992-04-30 | 1997-01-28 | Neurogen Corporation | Gabaa receptor subtypes and methods for screening drug compounds using imidazoquinoxalines and pyrrolopyrimidines to bind to gabaa receptor subtypes |
| JPH0665237A (ja) | 1992-05-07 | 1994-03-08 | Nissan Chem Ind Ltd | 置換ピラゾール誘導体および農園芸用殺菌剤 |
| PT672042E (pt) | 1993-10-01 | 2006-08-31 | Novartis Ag | Derivados de pirimidinoamina farmacologicamente activos e processos para a sua preparacao |
| EP0788358B1 (en) | 1994-11-10 | 2004-03-31 | Millennium Pharmaceuticals, Inc. | Use of pyrazole compounds for the treatment of glomerulonephritis, cancer, atherosclerosis or restenosis |
| IL117659A (en) | 1995-04-13 | 2000-12-06 | Dainippon Pharmaceutical Co | Substituted 2-phenyl pyrimidino amino acetamide derivative process for preparing the same and a pharmaceutical composition containing same |
| AU726058B2 (en) | 1995-09-01 | 2000-10-26 | Signal Pharmaceuticals, Inc. | Pyrimidine carboxylates and related compounds and methods for treating inflammatory conditions |
| US5935966A (en) | 1995-09-01 | 1999-08-10 | Signal Pharmaceuticals, Inc. | Pyrimidine carboxylates and related compounds and methods for treating inflammatory conditions |
| GB9523675D0 (en) | 1995-11-20 | 1996-01-24 | Celltech Therapeutics Ltd | Chemical compounds |
| US6716575B2 (en) | 1995-12-18 | 2004-04-06 | Sugen, Inc. | Diagnosis and treatment of AUR1 and/or AUR2 related disorders |
| WO1998002434A1 (en) | 1996-07-13 | 1998-01-22 | Glaxo Group Limited | Fused heterocyclic compounds as protein tyrosine kinase inhibitors |
| JPH10130150A (ja) | 1996-09-05 | 1998-05-19 | Dainippon Pharmaceut Co Ltd | 酢酸アミド誘導体からなる医薬 |
| GB9619284D0 (en) | 1996-09-16 | 1996-10-30 | Celltech Therapeutics Ltd | Chemical compounds |
| WO1998014450A1 (en) | 1996-10-02 | 1998-04-09 | Novartis Ag | Pyrimidine derivatives and processes for the preparation thereof |
| AU738341B2 (en) | 1996-10-11 | 2001-09-13 | Abbott Gmbh & Co. Kg | Asparate ester inhibitors of interleukin-1beta converting enzyme |
| DE19710435A1 (de) * | 1997-03-13 | 1998-09-17 | Hoechst Ag | Verwendung von Pyrimidinderivaten zur Prävention von Krebs allein oder in Kombination mit anderen therapeutischen Maßnahmen |
| WO1999018781A1 (en) | 1997-10-10 | 1999-04-22 | Cytovia, Inc. | Dipeptide apoptosis inhibitors and the use thereof |
| US6267952B1 (en) | 1998-01-09 | 2001-07-31 | Geltex Pharmaceuticals, Inc. | Lipase inhibiting polymers |
| JP2000026421A (ja) | 1998-01-29 | 2000-01-25 | Kumiai Chem Ind Co Ltd | ジアリ―ルスルフィド誘導体及び有害生物防除剤 |
| ATE245641T1 (de) | 1998-02-17 | 2003-08-15 | Tularik Inc | Antivirale pyrimidinderivate |
| US6153591A (en) | 1998-03-16 | 2000-11-28 | Cytovia, Inc. | Dipeptide caspase inhibitors and the use thereof |
| PL204628B1 (pl) | 1998-06-02 | 2010-01-29 | Osi Pharmaceuticals | Pochodna pirolo[2,3d]pirymidyny, jej zastosowanie i sposoby wytwarzania tej pochodnej i preparaty farmaceutyczne |
| KR100581199B1 (ko) * | 1998-06-19 | 2006-05-17 | 카이론 코포레이션 | 글리코겐 신타제 키나제 3의 억제제 |
| WO2000003901A1 (de) * | 1998-07-16 | 2000-01-27 | Continental Teves Ag & Co. Ohg | Verfahren und vorrichtung zum ermitteln von kritischen fahrzuständen bei im fahrbetrieb befindlichen fahrzeugen |
| WO2000011003A1 (en) | 1998-08-21 | 2000-03-02 | Du Pont Pharmaceuticals Company | ISOXAZOLO[4,5-d]PYRIMIDINES AS CRF ANTAGONISTS |
| US6184226B1 (en) | 1998-08-28 | 2001-02-06 | Scios Inc. | Quinazoline derivatives as inhibitors of P-38 α |
| DE69925141T2 (de) * | 1998-10-08 | 2006-04-27 | Astrazeneca Ab | Chinazolin derivate |
| GB9828640D0 (en) | 1998-12-23 | 1999-02-17 | Smithkline Beecham Plc | Novel method and compounds |
| GB9828511D0 (en) | 1998-12-24 | 1999-02-17 | Zeneca Ltd | Chemical compounds |
| DE69926914T2 (de) | 1999-01-13 | 2006-06-29 | Warner-Lambert Co. Llc | 1-heterozyklus-substituierte diarylaminen |
| GB9905075D0 (en) * | 1999-03-06 | 1999-04-28 | Zeneca Ltd | Chemical compounds |
| EP1165085B1 (en) | 1999-03-30 | 2006-06-14 | Novartis AG | Phthalazine derivatives for treating inflammatory diseases |
| WO2000078757A1 (en) | 1999-06-17 | 2000-12-28 | Shionogi Bioresearch Corp. | Inhibitors of il-12 production |
| GB9914258D0 (en) | 1999-06-18 | 1999-08-18 | Celltech Therapeutics Ltd | Chemical compounds |
| AR032130A1 (es) | 1999-08-13 | 2003-10-29 | Vertex Pharma | Un compuesto inhibidor de quinasas proteicas, una composicion farmaceutica que lo incluye, y un metodo para tratar afecciones con dicho compuesto |
| CA2386218A1 (en) | 1999-10-07 | 2001-04-12 | Amgen Inc. | Triazine kinase inhibitors |
| AU1047601A (en) | 1999-11-30 | 2001-06-12 | Pfizer Products Inc. | 2,4-diaminopyrimidine compounds useful as immunosuppressants |
| DK1246623T3 (da) | 1999-12-02 | 2006-11-13 | Osi Pharm Inc | Forbindelser, som er specifikke for adenosin A1-, A2a- og A3-receptor og anvendelser deraf |
| US6376489B1 (en) | 1999-12-23 | 2002-04-23 | Icos Corporation | Cyclic AMP-specific phosphodiesterase inhibitors |
| MY125768A (en) | 1999-12-15 | 2006-08-30 | Bristol Myers Squibb Co | N-[5-[[[5-alkyl-2-oxazolyl]methyl]thio]-2-thiazolyl]-carboxamide inhibitors of cyclin dependent kinases |
| US20020065270A1 (en) | 1999-12-28 | 2002-05-30 | Moriarty Kevin Joseph | N-heterocyclic inhibitors of TNF-alpha expression |
| JP2003519143A (ja) | 1999-12-28 | 2003-06-17 | ファーマコピーア,インコーポレーティッド | ピリミジン及びトリアジン系キナーゼ阻害剤 |
| AU782775B2 (en) | 2000-02-05 | 2005-08-25 | Vertex Pharmaceuticals Incorporated | Pyrazole compositions useful as inhibitors of ERK |
| CA2400447C (en) * | 2000-02-17 | 2008-04-22 | Amgen Inc. | Kinase inhibitors |
| GB0004887D0 (en) | 2000-03-01 | 2000-04-19 | Astrazeneca Uk Ltd | Chemical compounds |
| GB0004890D0 (en) * | 2000-03-01 | 2000-04-19 | Astrazeneca Uk Ltd | Chemical compounds |
| ATE297946T1 (de) | 2000-04-03 | 2005-07-15 | Vertex Pharma | Inhibitoren von serin proteasen, speziell der hepatitis-c-virus ns3-protease |
| CA2398446A1 (en) | 2000-04-18 | 2001-10-25 | Agouron Pharmaceuticals, Inc. | Pyrazoles for inhibiting protein kinases |
| JP3890184B2 (ja) * | 2000-05-15 | 2007-03-07 | Necパーソナルプロダクツ株式会社 | 電源装置及びその電力制御方法、情報処理機器 |
| EE200200715A (et) | 2000-06-28 | 2004-08-16 | Astrazeneca Ab | Asendatud kinasoliini derivaadid ja nende kasutamine inhibiitoritena |
| SI1385870T1 (sl) | 2000-07-21 | 2010-08-31 | Schering Corp | Peptidi kot NS3-serin proteazni inhibitorji virusa hepatitisa C |
| HRP20030140A2 (en) | 2000-08-31 | 2003-04-30 | Pfizer Prod Inc | Pyrazole derivatives and their use as protein kinase inhibitors |
| US6660731B2 (en) | 2000-09-15 | 2003-12-09 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| JP4052573B2 (ja) | 2000-09-15 | 2008-02-27 | バーテックス ファーマシューティカルズ インコーポレイテッド | イソオキサゾールおよびerkのインヒビターとしてのその使用 |
| US7473691B2 (en) | 2000-09-15 | 2009-01-06 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| US6613776B2 (en) | 2000-09-15 | 2003-09-02 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| WO2002022605A1 (en) | 2000-09-15 | 2002-03-21 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| US6610677B2 (en) | 2000-09-15 | 2003-08-26 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| PL359920A1 (en) | 2000-09-20 | 2004-09-06 | Merck Patent Gmbh | 4-amino-quinazolines |
| US6641579B1 (en) * | 2000-09-29 | 2003-11-04 | Spectrasonics Imaging, Inc. | Apparatus and method for ablating cardiac tissue |
| DE10061863A1 (de) | 2000-12-12 | 2002-06-13 | Basf Ag | Verfahren zur Herstellung von Triethylendiamin (TEDA) |
| US6716851B2 (en) | 2000-12-12 | 2004-04-06 | Cytovia, Inc. | Substituted 2-aryl-4-arylaminopyrimidines and analogs as activators or caspases and inducers of apoptosis and the use thereof |
| AU2002228922A1 (en) | 2000-12-12 | 2002-06-24 | Cytovia, Inc. | Substituted 2-aryl-4-arylaminopyrimidines and analogs as activators of caspases and inducers of apoptosis and the use thereof |
| AP2003002825A0 (en) | 2000-12-21 | 2003-09-30 | Vertex Pharma | Pyrazole compounds useful as protein kinase inhibitors |
| MY130778A (en) | 2001-02-09 | 2007-07-31 | Vertex Pharma | Heterocyclic inhibitiors of erk2 and uses thereof |
| ES2292753T4 (es) | 2001-03-29 | 2009-02-16 | Vertex Pharmaceuticals Incorporated | Inhibidores de quinasas n-terminales c-jun (jnk) y otras proteina quinasas. |
| AU2002338642A1 (en) | 2001-04-13 | 2002-10-28 | Vertex Pharmaceuticals Incorporated | Inhibitors of c-jun n-terminal kinases (jnk) and other protein kinases |
| EP1383771A1 (en) | 2001-04-20 | 2004-01-28 | Vertex Pharmaceuticals Incorporated | 9-deazaguanine derivatives as inhibitors of gsk-3 |
| CA2446864C (en) | 2001-05-16 | 2011-02-15 | Vertex Pharmaceuticals Incorporated | Inhibitors of src and other protein kinases |
| EP1399440B1 (en) | 2001-06-15 | 2009-06-03 | Vertex Pharmaceuticals Incorporated | 5-(2-aminopyrimidin-4-yl)benzisoxazoles as protein kinase inhibitors |
| ATE337312T1 (de) | 2001-07-03 | 2006-09-15 | Vertex Pharma | Isoxazolyl-pyrimidines als inhibitoren von src- und lck-protein-kinasen |
| WO2003026666A1 (en) * | 2001-09-26 | 2003-04-03 | Bayer Pharmaceuticals Corporation | 2-phenylamino-4- (5-pyrazolylamino)-pyrimidine derivatives as kinase inhibitors, in particular, as src kinase inhibitors |
| US6569499B2 (en) * | 2001-10-02 | 2003-05-27 | Xerox Corporation | Apparatus and method for coating photoreceptor substrates |
| AU2002364536B2 (en) | 2001-12-07 | 2008-10-23 | Vertex Pharmaceuticals, Inc. | Pyrimidine-based compounds useful as GSK-3 inhibitors |
| AU2003220300A1 (en) | 2002-03-15 | 2003-09-29 | Binch, Hayley | Compositions useful as inhibitors of protein kinases |
| US7091343B2 (en) | 2002-03-15 | 2006-08-15 | Vertex Pharmaceuticals Incorporated | Compositions useful as inhibitors of protein kinases |
| US7179826B2 (en) | 2002-03-15 | 2007-02-20 | Vertex Pharmaceuticals Incorporated | Compositions useful as inhibitors of protein kinases |
| US20040009981A1 (en) | 2002-03-15 | 2004-01-15 | David Bebbington | Compositions useful as inhibitors of protein kinases |
| US20030207873A1 (en) | 2002-04-10 | 2003-11-06 | Edmund Harrington | Inhibitors of Src and other protein kinases |
| EP1506189A1 (en) | 2002-04-26 | 2005-02-16 | Vertex Pharmaceuticals Incorporated | Pyrrole derivatives as inhibitors of erk2 and uses thereof |
| MY141867A (en) | 2002-06-20 | 2010-07-16 | Vertex Pharma | Substituted pyrimidines useful as protein kinase inhibitors |
| JP4570955B2 (ja) | 2002-07-09 | 2010-10-27 | バーテクス ファーマスーティカルズ インコーポレイテッド | プロテインキナーゼ阻害活性を持つイミダゾール類 |
| ATE339419T1 (de) | 2002-08-02 | 2006-10-15 | Vertex Pharma | Pyrazolenthaltende zusammensetzungen und ihre verwendung als gsk-3 inhibitoren |
| EP1928456B1 (en) | 2005-09-30 | 2015-04-22 | Miikana Therapeutics, Inc. | Substituted pyrazole compounds |
| NZ577768A (en) | 2006-12-19 | 2012-01-12 | Vertex Pharma | Aminopyrimidines useful as inhibitors of protein kinases |
-
2001
- 2001-12-19 AP APAP/P/2003/002825A patent/AP2003002825A0/en unknown
- 2001-12-19 PL PL363244A patent/PL210414B1/pl not_active IP Right Cessation
- 2001-12-19 KR KR10-2003-7008415A patent/KR20030061858A/ko not_active Abandoned
- 2001-12-19 WO PCT/US2001/049139 patent/WO2002066461A1/en not_active Ceased
- 2001-12-19 AT AT01271061T patent/ATE327989T1/de active
- 2001-12-19 NZ NZ526468A patent/NZ526468A/en not_active IP Right Cessation
- 2001-12-19 DE DE60119775T patent/DE60119775T2/de not_active Expired - Lifetime
- 2001-12-19 KR KR1020037008427A patent/KR100875091B1/ko not_active Expired - Fee Related
- 2001-12-19 NZ NZ526470A patent/NZ526470A/xx not_active IP Right Cessation
- 2001-12-19 MX MXPA03005609A patent/MXPA03005609A/es active IP Right Grant
- 2001-12-19 JP JP2002559413A patent/JP4160392B2/ja not_active Expired - Fee Related
- 2001-12-19 CN CN2011101042845A patent/CN102250071A/zh active Pending
- 2001-12-19 WO PCT/US2001/049401 patent/WO2002057259A2/en not_active Ceased
- 2001-12-19 HU HU0400842A patent/HUP0400842A2/hu unknown
- 2001-12-19 DE DE60119776T patent/DE60119776T2/de not_active Expired - Lifetime
- 2001-12-19 AT AT01273861T patent/ATE354573T1/de active
- 2001-12-19 KR KR1020037008385A patent/KR100889246B1/ko not_active Expired - Fee Related
- 2001-12-19 US US10/026,975 patent/US6653300B2/en not_active Expired - Fee Related
- 2001-12-19 KR KR1020037008397A patent/KR100947185B1/ko not_active Expired - Fee Related
- 2001-12-19 BR BR0116493-7A patent/BR0116493A/pt not_active IP Right Cessation
- 2001-12-19 HU HU0400638A patent/HUP0400638A2/hu unknown
- 2001-12-19 IL IL15636901A patent/IL156369A0/xx active IP Right Grant
- 2001-12-19 ES ES06011799T patent/ES2375491T3/es not_active Expired - Lifetime
- 2001-12-19 CA CA002432131A patent/CA2432131C/en not_active Expired - Fee Related
- 2001-12-19 CA CA002432799A patent/CA2432799C/en not_active Expired - Fee Related
- 2001-12-19 DE DE60123283T patent/DE60123283T2/de not_active Expired - Lifetime
- 2001-12-19 CA CA2432303A patent/CA2432303C/en not_active Expired - Fee Related
- 2001-12-19 SI SI200130656T patent/SI1353916T1/sl unknown
- 2001-12-19 PT PT01273861T patent/PT1355905E/pt unknown
- 2001-12-19 CN CNB01822105XA patent/CN100406454C/zh not_active Expired - Fee Related
- 2001-12-19 ES ES01993360T patent/ES2265450T3/es not_active Expired - Lifetime
- 2001-12-19 EP EP01985059A patent/EP1345925B1/en not_active Expired - Lifetime
- 2001-12-19 ES ES01985059T patent/ES2265446T3/es not_active Expired - Lifetime
- 2001-12-19 EP EP01994510A patent/EP1345927B1/en not_active Expired - Lifetime
- 2001-12-19 JP JP2002557938A patent/JP4210520B2/ja not_active Expired - Fee Related
- 2001-12-19 CN CNB01822136XA patent/CN100340555C/zh not_active Expired - Fee Related
- 2001-12-19 ES ES01271061T patent/ES2266095T3/es not_active Expired - Lifetime
- 2001-12-19 ES ES01994323T patent/ES2272567T3/es not_active Expired - Lifetime
- 2001-12-19 PT PT01271061T patent/PT1345922E/pt unknown
- 2001-12-19 HU HU0400641A patent/HUP0400641A3/hu unknown
- 2001-12-19 NZ NZ526473A patent/NZ526473A/en not_active IP Right Cessation
- 2001-12-19 CA CA002432222A patent/CA2432222C/en not_active Expired - Fee Related
- 2001-12-19 IL IL15636801A patent/IL156368A0/xx not_active IP Right Cessation
- 2001-12-19 DK DK01273861T patent/DK1355905T3/da active
- 2001-12-19 AT AT01994510T patent/ATE326462T1/de active
- 2001-12-19 KR KR1020037008409A patent/KR100909665B1/ko not_active Expired - Fee Related
- 2001-12-19 WO PCT/US2001/051120 patent/WO2002059111A2/en not_active Ceased
- 2001-12-19 EP EP01271061A patent/EP1345922B1/en not_active Expired - Lifetime
- 2001-12-19 EP EP01994323A patent/EP1353916B1/en not_active Expired - Lifetime
- 2001-12-19 US US10/026,967 patent/US6989385B2/en not_active Expired - Fee Related
- 2001-12-19 JP JP2002551561A patent/JP4160389B2/ja not_active Expired - Fee Related
- 2001-12-19 EP EP01273861A patent/EP1355905B1/en not_active Expired - Lifetime
- 2001-12-19 CN CNB018221351A patent/CN100408573C/zh not_active Expired - Fee Related
- 2001-12-19 AT AT01985059T patent/ATE326460T1/de active
- 2001-12-19 PT PT01994323T patent/PT1353916E/pt unknown
- 2001-12-19 NZ NZ526472A patent/NZ526472A/en not_active IP Right Cessation
- 2001-12-19 IL IL15640801A patent/IL156408A0/xx unknown
- 2001-12-19 HU HU0400639A patent/HUP0400639A3/hu unknown
- 2001-12-19 NZ NZ526471A patent/NZ526471A/en not_active IP Right Cessation
- 2001-12-19 DE DE60119774T patent/DE60119774T2/de not_active Expired - Lifetime
- 2001-12-19 PL PL363246A patent/PL210066B1/pl unknown
- 2001-12-19 WO PCT/US2001/050312 patent/WO2002068415A1/en not_active Ceased
- 2001-12-19 MX MXPA03005610A patent/MXPA03005610A/es active IP Right Grant
- 2001-12-19 CA CA002432129A patent/CA2432129C/en not_active Expired - Fee Related
- 2001-12-19 AT AT01994323T patent/ATE340172T1/de active
- 2001-12-19 WO PCT/US2001/051031 patent/WO2002062789A1/en not_active Ceased
- 2001-12-19 AU AU2001297619A patent/AU2001297619B2/en not_active Ceased
- 2001-12-19 KR KR1020037008387A patent/KR100843114B1/ko not_active Expired - Fee Related
- 2001-12-19 DK DK01271061T patent/DK1345922T3/da active
- 2001-12-19 NZ NZ526469A patent/NZ526469A/en not_active IP Right Cessation
- 2001-12-19 AT AT01993360T patent/ATE326461T1/de active
- 2001-12-19 HU HU0400908A patent/HUP0400908A3/hu unknown
- 2001-12-19 CA CA002432223A patent/CA2432223C/en not_active Expired - Fee Related
- 2001-12-19 ES ES01273861T patent/ES2280313T3/es not_active Expired - Lifetime
- 2001-12-19 ES ES01994510T patent/ES2265452T3/es not_active Expired - Lifetime
- 2001-12-19 DE DE60120219T patent/DE60120219T2/de not_active Expired - Lifetime
- 2001-12-19 AU AU2002234047A patent/AU2002234047A1/en not_active Abandoned
- 2001-12-19 JP JP2002567928A patent/JP4234435B2/ja not_active Expired - Fee Related
- 2001-12-19 MX MXPA03005607A patent/MXPA03005607A/es active IP Right Grant
- 2001-12-19 RU RU2003122209/04A patent/RU2355688C2/ru not_active IP Right Cessation
- 2001-12-19 WO PCT/US2001/049140 patent/WO2002050065A2/en not_active Ceased
- 2001-12-19 DE DE60126828T patent/DE60126828T2/de not_active Expired - Lifetime
- 2001-12-19 AP APAP/P/2003/002816A patent/AP1588A/en active
- 2001-12-19 EP EP01993360A patent/EP1345926B1/en not_active Expired - Lifetime
- 2001-12-19 SI SI200130722T patent/SI1355905T1/sl unknown
- 2001-12-19 EP EP10184271A patent/EP2264028A1/en not_active Withdrawn
- 2001-12-19 AU AU2002255452A patent/AU2002255452B2/en not_active Ceased
- 2001-12-19 US US10/025,164 patent/US6664247B2/en not_active Expired - Fee Related
- 2001-12-19 US US10/026,966 patent/US20030105090A1/en not_active Abandoned
- 2001-12-19 US US10/027,001 patent/US6653301B2/en not_active Expired - Fee Related
- 2001-12-19 US US10/026,992 patent/US7625913B2/en not_active Expired - Fee Related
- 2001-12-19 JP JP2002565976A patent/JP2004518743A/ja active Pending
- 2001-12-19 MX MXPA03005606A patent/MXPA03005606A/es active IP Right Grant
- 2001-12-19 BR BR0116411-2A patent/BR0116411A/pt not_active IP Right Cessation
- 2001-12-19 IL IL15640701A patent/IL156407A0/xx not_active IP Right Cessation
- 2001-12-19 DK DK01994323T patent/DK1353916T3/da active
- 2001-12-19 AT AT06011799T patent/ATE528303T1/de not_active IP Right Cessation
- 2001-12-19 MX MXPA03005605A patent/MXPA03005605A/es active IP Right Grant
- 2001-12-19 IL IL15638901A patent/IL156389A0/xx active IP Right Grant
- 2001-12-19 CN CNA018221033A patent/CN1486310A/zh active Pending
- 2001-12-19 EP EP06011799A patent/EP1702920B1/en not_active Expired - Lifetime
- 2001-12-19 CN CNB018221025A patent/CN100436452C/zh not_active Expired - Fee Related
- 2001-12-19 MX MXPA03005608A patent/MXPA03005608A/es not_active Application Discontinuation
- 2001-12-19 JP JP2002563142A patent/JP4160395B2/ja not_active Expired - Fee Related
- 2001-12-20 US US10/034,683 patent/US6656939B2/en not_active Expired - Fee Related
- 2001-12-20 CA CA002432132A patent/CA2432132C/en not_active Expired - Fee Related
- 2001-12-20 CA CA002432872A patent/CA2432872C/en not_active Expired - Fee Related
- 2001-12-20 AU AU2002231166A patent/AU2002231166B2/en not_active Ceased
- 2001-12-20 AR ARP010105962A patent/AR042169A1/es active IP Right Grant
- 2001-12-20 US US10/034,019 patent/US6727251B2/en not_active Expired - Fee Related
- 2001-12-20 NZ NZ526474A patent/NZ526474A/en unknown
- 2001-12-20 EP EP01994347A patent/EP1345929B1/en not_active Expired - Lifetime
- 2001-12-20 NZ NZ526475A patent/NZ526475A/en unknown
- 2001-12-20 MX MXPA03005612A patent/MXPA03005612A/es not_active Application Discontinuation
- 2001-12-20 WO PCT/US2001/049594 patent/WO2002059112A2/en not_active Ceased
- 2001-12-20 AR ARP010105963A patent/AR040925A1/es active IP Right Grant
- 2001-12-20 JP JP2002559414A patent/JP2004517927A/ja active Pending
- 2001-12-20 KR KR10-2003-7008364A patent/KR20030061463A/ko not_active Abandoned
- 2001-12-20 KR KR10-2003-7008366A patent/KR20030061464A/ko not_active Withdrawn
- 2001-12-20 MX MXPA03005611A patent/MXPA03005611A/es unknown
- 2001-12-20 EP EP01991439A patent/EP1345928B1/en not_active Expired - Lifetime
- 2001-12-20 DE DE60119777T patent/DE60119777T2/de not_active Expired - Lifetime
- 2001-12-20 AR ARP010105960A patent/AR042397A1/es active IP Right Grant
- 2001-12-20 DE DE60126658T patent/DE60126658T2/de not_active Expired - Lifetime
- 2001-12-20 JP JP2002551562A patent/JP2004516292A/ja active Pending
- 2001-12-20 AU AU3116602A patent/AU3116602A/xx active Pending
- 2001-12-20 AU AU2002246754A patent/AU2002246754B2/en not_active Ceased
- 2001-12-20 AR ARP010105961A patent/AR042398A1/es unknown
- 2001-12-20 AT AT01991439T patent/ATE353890T1/de not_active IP Right Cessation
- 2001-12-20 WO PCT/US2001/049585 patent/WO2002050066A2/en not_active Ceased
- 2001-12-20 AT AT01994347T patent/ATE326463T1/de not_active IP Right Cessation
- 2001-12-21 MY MYPI20015823A patent/MY140377A/en unknown
- 2001-12-25 TW TW095139649A patent/TWI313269B/zh not_active IP Right Cessation
- 2001-12-25 TW TW090131846A patent/TWI290551B/zh not_active IP Right Cessation
-
2003
- 2003-06-10 IL IL156369A patent/IL156369A/en not_active IP Right Cessation
- 2003-06-11 IL IL156389A patent/IL156389A/en not_active IP Right Cessation
- 2003-06-12 NO NO20032671A patent/NO20032671L/no not_active Application Discontinuation
- 2003-06-12 NO NO20032670A patent/NO328537B1/no not_active IP Right Cessation
- 2003-06-13 NO NO20032704A patent/NO330527B1/no not_active IP Right Cessation
- 2003-06-13 NO NO20032703A patent/NO328501B1/no not_active IP Right Cessation
- 2003-06-16 NO NO20032736A patent/NO20032736L/no unknown
- 2003-08-01 US US10/632,428 patent/US7531536B2/en not_active Expired - Fee Related
- 2003-11-25 US US10/722,374 patent/US20040157893A1/en not_active Abandoned
- 2003-12-15 US US10/736,426 patent/US7087603B2/en not_active Expired - Fee Related
-
2004
- 2004-02-10 US US10/775,699 patent/US7427681B2/en not_active Expired - Fee Related
- 2004-12-17 JP JP2004366925A patent/JP2005097322A/ja not_active Withdrawn
-
2006
- 2006-03-21 AU AU2006201267A patent/AU2006201267B2/en not_active Ceased
- 2006-12-20 CY CY20061101823T patent/CY1106297T1/el unknown
-
2008
- 2008-04-01 JP JP2008095584A patent/JP2008260767A/ja not_active Withdrawn
- 2008-04-01 JP JP2008095581A patent/JP2008189682A/ja not_active Withdrawn
- 2008-04-03 JP JP2008097620A patent/JP2008222719A/ja active Pending
- 2008-04-04 JP JP2008098506A patent/JP2008189687A/ja active Pending
- 2008-04-25 US US12/109,598 patent/US8304414B2/en not_active Expired - Fee Related
- 2008-05-07 JP JP2008121723A patent/JP2008201808A/ja active Pending
- 2008-05-07 JP JP2008121727A patent/JP2008247921A/ja active Pending
- 2008-05-07 JP JP2008121724A patent/JP2008247920A/ja active Pending
-
2009
- 2009-04-17 JP JP2009101481A patent/JP5249842B2/ja not_active Expired - Fee Related
- 2009-08-21 US US12/545,347 patent/US7982037B2/en not_active Expired - Fee Related
- 2009-09-14 JP JP2009212566A patent/JP2009286805A/ja not_active Withdrawn
-
2010
- 2010-12-07 IL IL209827A patent/IL209827A0/en unknown
-
2012
- 2012-09-28 US US13/631,488 patent/US8697698B2/en not_active Expired - Fee Related
-
2013
- 2013-07-19 JP JP2013150948A patent/JP2013213068A/ja active Pending
- 2013-12-24 US US14/139,889 patent/US20140187772A1/en not_active Abandoned
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TWI313269B (en) | Pyrazole compounds useful as protein kinase inhibitors | |
| AU2002255452A1 (en) | Pyrazole compounds useful as protein kinase inhibitors | |
| RU2332415C2 (ru) | Производные пиразола, полезные в качестве ингибиторов протеинкиназы | |
| HK1062565B (en) | Pyrazole compounds useful as protein kinase inhibitors |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Annulment or lapse of patent due to non-payment of fees |