ES2380795T3 - Pirrolopiridinas útiles como inhibidores de proteínas quinasas - Google Patents
Pirrolopiridinas útiles como inhibidores de proteínas quinasas Download PDFInfo
- Publication number
- ES2380795T3 ES2380795T3 ES06770824T ES06770824T ES2380795T3 ES 2380795 T3 ES2380795 T3 ES 2380795T3 ES 06770824 T ES06770824 T ES 06770824T ES 06770824 T ES06770824 T ES 06770824T ES 2380795 T3 ES2380795 T3 ES 2380795T3
- Authority
- ES
- Spain
- Prior art keywords
- compound according
- compound
- aliphatic
- disease
- mhz
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 title description 4
- 239000003909 protein kinase inhibitor Substances 0.000 title description 4
- 150000005255 pyrrolopyridines Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 318
- 239000000203 mixture Substances 0.000 claims abstract description 178
- 238000000034 method Methods 0.000 claims abstract description 95
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 80
- 238000011282 treatment Methods 0.000 claims abstract description 64
- 201000010099 disease Diseases 0.000 claims abstract description 43
- 239000011435 rock Substances 0.000 claims abstract description 26
- 108091000080 Phosphotransferase Proteins 0.000 claims abstract description 18
- 102000020233 phosphotransferase Human genes 0.000 claims abstract description 18
- 102000042838 JAK family Human genes 0.000 claims abstract description 8
- 108091082332 JAK family Proteins 0.000 claims abstract description 8
- -1 NCH3 Chemical group 0.000 claims description 120
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 114
- 125000001931 aliphatic group Chemical group 0.000 claims description 106
- 239000007787 solid Substances 0.000 claims description 64
- 229910052736 halogen Inorganic materials 0.000 claims description 63
- 239000003795 chemical substances by application Substances 0.000 claims description 55
- 201000006417 multiple sclerosis Diseases 0.000 claims description 54
- 150000002367 halogens Chemical group 0.000 claims description 52
- 125000001424 substituent group Chemical group 0.000 claims description 52
- 125000000623 heterocyclic group Chemical group 0.000 claims description 48
- 125000004429 atom Chemical group 0.000 claims description 47
- 239000003814 drug Substances 0.000 claims description 42
- 208000035475 disorder Diseases 0.000 claims description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 25
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- 229940124597 therapeutic agent Drugs 0.000 claims description 22
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 239000002552 dosage form Substances 0.000 claims description 19
- 238000004519 manufacturing process Methods 0.000 claims description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
- 230000000694 effects Effects 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 15
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 15
- 208000006673 asthma Diseases 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- 230000002401 inhibitory effect Effects 0.000 claims description 14
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 13
- 208000010228 Erectile Dysfunction Diseases 0.000 claims description 13
- 201000001881 impotence Diseases 0.000 claims description 13
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 13
- 206010007572 Cardiac hypertrophy Diseases 0.000 claims description 12
- 206010020772 Hypertension Diseases 0.000 claims description 12
- 206010028980 Neoplasm Diseases 0.000 claims description 12
- 230000009467 reduction Effects 0.000 claims description 12
- 239000012472 biological sample Substances 0.000 claims description 11
- 201000011510 cancer Diseases 0.000 claims description 11
- 206010012601 diabetes mellitus Diseases 0.000 claims description 11
- 208000028867 ischemia Diseases 0.000 claims description 11
- 230000010410 reperfusion Effects 0.000 claims description 11
- 208000010412 Glaucoma Diseases 0.000 claims description 10
- 230000001404 mediated effect Effects 0.000 claims description 10
- 229920006395 saturated elastomer Polymers 0.000 claims description 10
- 208000024827 Alzheimer disease Diseases 0.000 claims description 9
- 206010003225 Arteriospasm coronary Diseases 0.000 claims description 9
- 201000001320 Atherosclerosis Diseases 0.000 claims description 9
- 208000023275 Autoimmune disease Diseases 0.000 claims description 9
- 208000006029 Cardiomegaly Diseases 0.000 claims description 9
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 9
- 208000003890 Coronary Vasospasm Diseases 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- 201000011634 coronary artery vasospasm Diseases 0.000 claims description 9
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 9
- 125000001188 haloalkyl group Chemical group 0.000 claims description 9
- 208000001286 intracranial vasospasm Diseases 0.000 claims description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
- 208000011231 Crohn disease Diseases 0.000 claims description 8
- 206010020751 Hypersensitivity Diseases 0.000 claims description 8
- 230000002792 vascular Effects 0.000 claims description 8
- 208000030507 AIDS Diseases 0.000 claims description 7
- 206010002383 Angina Pectoris Diseases 0.000 claims description 7
- 208000029462 Immunodeficiency disease Diseases 0.000 claims description 7
- 208000014767 Myeloproliferative disease Diseases 0.000 claims description 7
- 206010052779 Transplant rejections Diseases 0.000 claims description 7
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 7
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 7
- 230000001028 anti-proliverative effect Effects 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 230000004663 cell proliferation Effects 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 239000003018 immunosuppressive agent Substances 0.000 claims description 7
- 210000000056 organ Anatomy 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 208000020084 Bone disease Diseases 0.000 claims description 6
- 108010025020 Nerve Growth Factor Proteins 0.000 claims description 6
- 102000007072 Nerve Growth Factors Human genes 0.000 claims description 6
- 208000003782 Raynaud disease Diseases 0.000 claims description 6
- 208000012322 Raynaud phenomenon Diseases 0.000 claims description 6
- 208000006011 Stroke Diseases 0.000 claims description 6
- 208000027418 Wounds and injury Diseases 0.000 claims description 6
- 239000002671 adjuvant Substances 0.000 claims description 6
- 230000000973 chemotherapeutic effect Effects 0.000 claims description 6
- 230000006378 damage Effects 0.000 claims description 6
- 208000014674 injury Diseases 0.000 claims description 6
- 239000003900 neurotrophic factor Substances 0.000 claims description 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 5
- 208000019838 Blood disease Diseases 0.000 claims description 5
- 206010016654 Fibrosis Diseases 0.000 claims description 5
- 206010061598 Immunodeficiency Diseases 0.000 claims description 5
- 206010025323 Lymphomas Diseases 0.000 claims description 5
- 208000018737 Parkinson disease Diseases 0.000 claims description 5
- 206010036595 Premature delivery Diseases 0.000 claims description 5
- 239000003443 antiviral agent Substances 0.000 claims description 5
- 125000002619 bicyclic group Chemical group 0.000 claims description 5
- 230000004761 fibrosis Effects 0.000 claims description 5
- 208000014951 hematologic disease Diseases 0.000 claims description 5
- 208000018706 hematopoietic system disease Diseases 0.000 claims description 5
- 230000002519 immonomodulatory effect Effects 0.000 claims description 5
- 230000007813 immunodeficiency Effects 0.000 claims description 5
- 229940125721 immunosuppressive agent Drugs 0.000 claims description 5
- 208000032839 leukemia Diseases 0.000 claims description 5
- 208000019423 liver disease Diseases 0.000 claims description 5
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 5
- 230000002062 proliferating effect Effects 0.000 claims description 5
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 5
- 201000000980 schizophrenia Diseases 0.000 claims description 5
- 201000004384 Alopecia Diseases 0.000 claims description 4
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 208000020446 Cardiac disease Diseases 0.000 claims description 4
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims description 4
- 206010012289 Dementia Diseases 0.000 claims description 4
- 206010048554 Endothelial dysfunction Diseases 0.000 claims description 4
- 208000023105 Huntington disease Diseases 0.000 claims description 4
- 206010020880 Hypertrophy Diseases 0.000 claims description 4
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims description 4
- 201000007224 Myeloproliferative neoplasm Diseases 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 230000007815 allergy Effects 0.000 claims description 4
- 206010009887 colitis Diseases 0.000 claims description 4
- 230000001066 destructive effect Effects 0.000 claims description 4
- 230000008694 endothelial dysfunction Effects 0.000 claims description 4
- 230000003676 hair loss Effects 0.000 claims description 4
- 208000019622 heart disease Diseases 0.000 claims description 4
- 201000005787 hematologic cancer Diseases 0.000 claims description 4
- 208000027866 inflammatory disease Diseases 0.000 claims description 4
- 208000030603 inherited susceptibility to asthma Diseases 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 238000002054 transplantation Methods 0.000 claims description 4
- 230000003612 virological effect Effects 0.000 claims description 4
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 3
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 3
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 3
- 208000032027 Essential Thrombocythemia Diseases 0.000 claims description 3
- 208000009329 Graft vs Host Disease Diseases 0.000 claims description 3
- 206010048643 Hypereosinophilic syndrome Diseases 0.000 claims description 3
- 206010028561 Myeloid metaplasia Diseases 0.000 claims description 3
- 208000033833 Myelomonocytic Chronic Leukemia Diseases 0.000 claims description 3
- 208000001132 Osteoporosis Diseases 0.000 claims description 3
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 3
- 208000017442 Retinal disease Diseases 0.000 claims description 3
- 206010038923 Retinopathy Diseases 0.000 claims description 3
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims description 3
- 201000008736 Systemic mastocytosis Diseases 0.000 claims description 3
- 208000017733 acquired polycythemia vera Diseases 0.000 claims description 3
- 208000026935 allergic disease Diseases 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 208000021668 chronic eosinophilic leukemia Diseases 0.000 claims description 3
- 201000010902 chronic myelomonocytic leukemia Diseases 0.000 claims description 3
- 230000008602 contraction Effects 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 208000024908 graft versus host disease Diseases 0.000 claims description 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 3
- 238000000338 in vitro Methods 0.000 claims description 3
- 206010028537 myelofibrosis Diseases 0.000 claims description 3
- 125000004043 oxo group Chemical group O=* 0.000 claims description 3
- 230000003836 peripheral circulation Effects 0.000 claims description 3
- 208000037244 polycythemia vera Diseases 0.000 claims description 3
- 208000003476 primary myelofibrosis Diseases 0.000 claims description 3
- 208000037803 restenosis Diseases 0.000 claims description 3
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- 201000003883 Cystic fibrosis Diseases 0.000 claims description 2
- 206010019842 Hepatomegaly Diseases 0.000 claims description 2
- 206010061218 Inflammation Diseases 0.000 claims description 2
- 201000004681 Psoriasis Diseases 0.000 claims description 2
- 208000028017 Psychotic disease Diseases 0.000 claims description 2
- 206010047163 Vasospasm Diseases 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 208000037824 growth disorder Diseases 0.000 claims description 2
- 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 claims description 2
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 2
- 230000004054 inflammatory process Effects 0.000 claims description 2
- 239000002955 immunomodulating agent Substances 0.000 claims 2
- 229960003444 immunosuppressant agent Drugs 0.000 claims 2
- 230000001861 immunosuppressant effect Effects 0.000 claims 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 2
- 229910006074 SO2NH2 Inorganic materials 0.000 claims 1
- 230000000172 allergic effect Effects 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 230000002584 immunomodulator Effects 0.000 claims 1
- 229940121354 immunomodulator Drugs 0.000 claims 1
- 102000001253 Protein Kinase Human genes 0.000 abstract description 7
- 108060006633 protein kinase Proteins 0.000 abstract description 7
- 239000003112 inhibitor Substances 0.000 abstract description 6
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 326
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 168
- 238000005481 NMR spectroscopy Methods 0.000 description 164
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 147
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 102
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 97
- 239000000243 solution Substances 0.000 description 77
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 71
- 235000019439 ethyl acetate Nutrition 0.000 description 65
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 59
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 50
- 238000006243 chemical reaction Methods 0.000 description 48
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 48
- 239000002904 solvent Substances 0.000 description 47
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 39
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
- 238000005160 1H NMR spectroscopy Methods 0.000 description 38
- 229940093499 ethyl acetate Drugs 0.000 description 38
- 239000011541 reaction mixture Substances 0.000 description 38
- 230000015572 biosynthetic process Effects 0.000 description 37
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 35
- 238000003786 synthesis reaction Methods 0.000 description 35
- 235000002639 sodium chloride Nutrition 0.000 description 32
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 229910052938 sodium sulfate Inorganic materials 0.000 description 30
- 235000011152 sodium sulphate Nutrition 0.000 description 30
- 239000007832 Na2SO4 Substances 0.000 description 26
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 26
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 20
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 18
- 239000012267 brine Substances 0.000 description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 18
- 239000000725 suspension Substances 0.000 description 18
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 17
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 108010024121 Janus Kinases Proteins 0.000 description 15
- 102000015617 Janus Kinases Human genes 0.000 description 15
- 239000002253 acid Substances 0.000 description 15
- 125000003118 aryl group Chemical group 0.000 description 15
- 239000012074 organic phase Substances 0.000 description 15
- 125000005843 halogen group Chemical group 0.000 description 14
- 239000003921 oil Substances 0.000 description 14
- 235000019198 oils Nutrition 0.000 description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
- 239000000546 pharmaceutical excipient Substances 0.000 description 14
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 14
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 13
- 239000012299 nitrogen atmosphere Substances 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 12
- 238000004128 high performance liquid chromatography Methods 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-UHFFFAOYSA-N 0.000 description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
- 230000002829 reductive effect Effects 0.000 description 11
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 10
- 238000004440 column chromatography Methods 0.000 description 10
- 238000002953 preparative HPLC Methods 0.000 description 10
- 230000005855 radiation Effects 0.000 description 10
- 239000003981 vehicle Substances 0.000 description 10
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000003556 assay Methods 0.000 description 9
- 238000004587 chromatography analysis Methods 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 238000000576 coating method Methods 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 229910052760 oxygen Inorganic materials 0.000 description 9
- 229920001223 polyethylene glycol Polymers 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- 238000000746 purification Methods 0.000 description 9
- 238000004007 reversed phase HPLC Methods 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- 229910000029 sodium carbonate Inorganic materials 0.000 description 9
- 235000017550 sodium carbonate Nutrition 0.000 description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 8
- 150000001408 amides Chemical class 0.000 description 8
- 125000004122 cyclic group Chemical group 0.000 description 8
- 238000003818 flash chromatography Methods 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- 229910052717 sulfur Inorganic materials 0.000 description 8
- 239000011593 sulfur Substances 0.000 description 8
- 239000003826 tablet Substances 0.000 description 8
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- 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 7
- 239000002775 capsule Substances 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 7
- 239000008101 lactose Substances 0.000 description 7
- 235000015320 potassium carbonate Nutrition 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 6
- HFUCVVCJXREYJQ-DFWYDOINSA-N (2s)-2-amino-n-(2,2,2-trifluoroethyl)propanamide;hydrochloride Chemical compound Cl.C[C@H](N)C(=O)NCC(F)(F)F HFUCVVCJXREYJQ-DFWYDOINSA-N 0.000 description 6
- PDGRKLDVDPKRSQ-UHFFFAOYSA-N 5-chloro-n-cyclopentyl-1h-pyrrolo[2,3-b]pyridin-4-amine Chemical compound ClC1=CN=C2NC=CC2=C1NC1CCCC1 PDGRKLDVDPKRSQ-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 101000934996 Homo sapiens Tyrosine-protein kinase JAK3 Proteins 0.000 description 6
- 102100025387 Tyrosine-protein kinase JAK3 Human genes 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 150000001721 carbon Chemical group 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- 231100000252 nontoxic Toxicity 0.000 description 6
- 230000003000 nontoxic effect Effects 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 239000000523 sample Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000001993 wax Substances 0.000 description 6
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 5
- 239000007995 HEPES buffer Substances 0.000 description 5
- 101000997832 Homo sapiens Tyrosine-protein kinase JAK2 Proteins 0.000 description 5
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 5
- 102100033444 Tyrosine-protein kinase JAK2 Human genes 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 5
- 239000000872 buffer Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 230000008878 coupling Effects 0.000 description 5
- 238000010168 coupling process Methods 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
- 239000010779 crude oil Substances 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 239000000314 lubricant Substances 0.000 description 5
- 239000006187 pill Substances 0.000 description 5
- 239000003755 preservative agent Substances 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- 239000000829 suppository Substances 0.000 description 5
- 230000000699 topical effect Effects 0.000 description 5
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 4
- FIMYFEGKMOCQKT-UHFFFAOYSA-N 3,4-difluoro-2-(2-fluoro-4-iodoanilino)-n-(2-hydroxyethoxy)-5-[(3-oxooxazinan-2-yl)methyl]benzamide Chemical compound FC=1C(F)=C(NC=2C(=CC(I)=CC=2)F)C(C(=O)NOCCO)=CC=1CN1OCCCC1=O FIMYFEGKMOCQKT-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- 108010050904 Interferons Proteins 0.000 description 4
- 102000014150 Interferons Human genes 0.000 description 4
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- 229930006000 Sucrose Natural products 0.000 description 4
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 235000010443 alginic acid Nutrition 0.000 description 4
- 229920000615 alginic acid Polymers 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 150000001543 aryl boronic acids Chemical class 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 4
- 150000001805 chlorine compounds Chemical class 0.000 description 4
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 4
- 239000003246 corticosteroid Substances 0.000 description 4
- 229960001334 corticosteroids Drugs 0.000 description 4
- 238000010511 deprotection reaction Methods 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 210000001035 gastrointestinal tract Anatomy 0.000 description 4
- 239000003701 inert diluent Substances 0.000 description 4
- 229940047124 interferons Drugs 0.000 description 4
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 239000002207 metabolite Substances 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 4
- 235000012239 silicon dioxide Nutrition 0.000 description 4
- 239000007909 solid dosage form Substances 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000005720 sucrose Substances 0.000 description 4
- 239000000375 suspending agent Substances 0.000 description 4
- AJBOCBHMUQDLCQ-YFKPBYRVSA-N (2s)-2-[(2-chloropyrimidin-4-yl)amino]-n-(2,2,2-trifluoroethyl)propanamide Chemical compound FC(F)(F)CNC(=O)[C@H](C)NC1=CC=NC(Cl)=N1 AJBOCBHMUQDLCQ-YFKPBYRVSA-N 0.000 description 3
- SAMANQYESBLODC-UHFFFAOYSA-N 2-(1h-pyrrolo[2,3-b]pyridin-4-yl)-1,3-thiazole-4-carboxylic acid Chemical compound OC(=O)C1=CSC(C=2C=3C=CNC=3N=CC=2)=N1 SAMANQYESBLODC-UHFFFAOYSA-N 0.000 description 3
- JENBYRMEJUIFGQ-UHFFFAOYSA-N 2-(6-chloropyridin-2-yl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)C1=CC=CC(Cl)=N1 JENBYRMEJUIFGQ-UHFFFAOYSA-N 0.000 description 3
- ZIDIKYIZXMYHAW-UHFFFAOYSA-N 2-bromo-6-fluoropyridine Chemical compound FC1=CC=CC(Br)=N1 ZIDIKYIZXMYHAW-UHFFFAOYSA-N 0.000 description 3
- YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 3
- SVMZMZXZHHXWKU-UHFFFAOYSA-N 3-(1h-pyrrolo[2,3-b]pyridin-4-yl)aniline Chemical compound NC1=CC=CC(C=2C=3C=CNC=3N=CC=2)=C1 SVMZMZXZHHXWKU-UHFFFAOYSA-N 0.000 description 3
- IMQVBCRZLIQNPG-UHFFFAOYSA-N 4-(1-methylpyrazol-4-yl)-1h-pyrrolo[2,3-b]pyridine Chemical compound C1=NN(C)C=C1C1=CC=NC2=C1C=CN2 IMQVBCRZLIQNPG-UHFFFAOYSA-N 0.000 description 3
- XQMRGXOLQZZOGI-UHFFFAOYSA-N 4-(1h-pyrrolo[2,3-b]pyridin-4-yl)-1h-pyrrole-2-carboxylic acid Chemical compound N1C(C(=O)O)=CC(C=2C=3C=CNC=3N=CC=2)=C1 XQMRGXOLQZZOGI-UHFFFAOYSA-N 0.000 description 3
- AGAZWHJMRYQMBI-UHFFFAOYSA-N 4-(3,4-dimethylphenyl)-1h-pyrrolo[2,3-b]pyridine Chemical compound C1=C(C)C(C)=CC=C1C1=CC=NC2=C1C=CN2 AGAZWHJMRYQMBI-UHFFFAOYSA-N 0.000 description 3
- BABPUBPSCWEVAE-UHFFFAOYSA-N 4-(3,5-dimethyl-1h-pyrazol-4-yl)-1h-pyrrolo[2,3-b]pyridine Chemical compound CC1=NNC(C)=C1C1=CC=NC2=C1C=CN2 BABPUBPSCWEVAE-UHFFFAOYSA-N 0.000 description 3
- DASVPLFTEBDCGU-UHFFFAOYSA-N 4-(3-propan-2-ylphenyl)-1h-pyrrolo[2,3-b]pyridine Chemical compound CC(C)C1=CC=CC(C=2C=3C=CNC=3N=CC=2)=C1 DASVPLFTEBDCGU-UHFFFAOYSA-N 0.000 description 3
- JSNCRUDROUTYBO-UHFFFAOYSA-N 4-(6-fluoropyridin-2-yl)-1h-pyrrolo[2,3-b]pyridine Chemical compound FC1=CC=CC(C=2C=3C=CNC=3N=CC=2)=N1 JSNCRUDROUTYBO-UHFFFAOYSA-N 0.000 description 3
- WUVVZVHSVCFVSW-UHFFFAOYSA-N 4-(furan-3-yl)-1h-pyrrolo[2,3-b]pyridine Chemical compound C1=CN=C2NC=CC2=C1C=1C=COC=1 WUVVZVHSVCFVSW-UHFFFAOYSA-N 0.000 description 3
- XWRZDBIWCPESJH-UHFFFAOYSA-N 4-[3-(trifluoromethyl)phenyl]-1h-pyrrolo[2,3-b]pyridine Chemical compound FC(F)(F)C1=CC=CC(C=2C=3C=CNC=3N=CC=2)=C1 XWRZDBIWCPESJH-UHFFFAOYSA-N 0.000 description 3
- UHOQDMKXJCJJGE-UHFFFAOYSA-N 4-bromo-5-chloro-1h-pyrrolo[2,3-b]pyridine Chemical compound ClC1=CN=C2NC=CC2=C1Br UHOQDMKXJCJJGE-UHFFFAOYSA-N 0.000 description 3
- IDQKIRACLMELKA-UHFFFAOYSA-N 4-pyrimidin-5-yl-1h-pyrrolo[2,3-b]pyridine Chemical compound C1=CN=C2NC=CC2=C1C1=CN=CN=C1 IDQKIRACLMELKA-UHFFFAOYSA-N 0.000 description 3
- JBYGOPUXGCZLDS-UHFFFAOYSA-N 5-(1h-pyrrolo[2,3-b]pyridin-4-yl)thiophene-2-carbonitrile Chemical compound S1C(C#N)=CC=C1C1=CC=NC2=C1C=CN2 JBYGOPUXGCZLDS-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 3
- 229940126062 Compound A Drugs 0.000 description 3
- 229920002261 Corn starch Polymers 0.000 description 3
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 3
- 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 3
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 3
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 3
- 239000006172 buffering agent Substances 0.000 description 3
- 235000019437 butane-1,3-diol Nutrition 0.000 description 3
- 239000001768 carboxy methyl cellulose Substances 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 229940110456 cocoa butter Drugs 0.000 description 3
- 235000019868 cocoa butter Nutrition 0.000 description 3
- 229910052681 coesite Inorganic materials 0.000 description 3
- 239000008120 corn starch Substances 0.000 description 3
- 229910052906 cristobalite Inorganic materials 0.000 description 3
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 3
- 229960004397 cyclophosphamide Drugs 0.000 description 3
- 230000003111 delayed effect Effects 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 229940043355 kinase inhibitor Drugs 0.000 description 3
- UHXYXWIGCSBFBR-UHFFFAOYSA-N n-[3-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(C=2C=3C=CNC=3N=CC=2)=C1 UHXYXWIGCSBFBR-UHFFFAOYSA-N 0.000 description 3
- IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 3
- 239000002674 ointment Substances 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
- 239000004006 olive oil Substances 0.000 description 3
- 235000008390 olive oil Nutrition 0.000 description 3
- 230000020477 pH reduction Effects 0.000 description 3
- 235000019271 petrolatum Nutrition 0.000 description 3
- 235000021317 phosphate Nutrition 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 239000003757 phosphotransferase inhibitor Substances 0.000 description 3
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 235000011056 potassium acetate Nutrition 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 3
- 229960004063 propylene glycol Drugs 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000008247 solid mixture Substances 0.000 description 3
- 229910052682 stishovite Inorganic materials 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 235000000346 sugar Nutrition 0.000 description 3
- 150000008163 sugars Chemical class 0.000 description 3
- 239000003765 sweetening agent Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- WORJEOGGNQDSOE-ASTXPPQBSA-N trichloro(deuterio)methane;trideuterio(deuteriooxy)methane Chemical compound [2H]C(Cl)(Cl)Cl.[2H]OC([2H])([2H])[2H] WORJEOGGNQDSOE-ASTXPPQBSA-N 0.000 description 3
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 3
- 229910052905 tridymite Inorganic materials 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- QAWXUPCNONFHQL-LURJTMIESA-N (2s)-2-[(6-bromopyridin-2-yl)amino]-n-(2,2,2-trifluoroethyl)propanamide Chemical compound FC(F)(F)CNC(=O)[C@H](C)NC1=CC=CC(Br)=N1 QAWXUPCNONFHQL-LURJTMIESA-N 0.000 description 2
- FNHHVPPSBFQMEL-KQHDFZBMSA-N (3S)-5-N-[(1S,5R)-3-hydroxy-6-bicyclo[3.1.0]hexanyl]-7-N,3-dimethyl-3-phenyl-2H-1-benzofuran-5,7-dicarboxamide Chemical compound CNC(=O)c1cc(cc2c1OC[C@@]2(C)c1ccccc1)C(=O)NC1[C@H]2CC(O)C[C@@H]12 FNHHVPPSBFQMEL-KQHDFZBMSA-N 0.000 description 2
- VXZHVNJQMHZXJB-UHFFFAOYSA-N (4-methylpiperazin-1-yl)-[3-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC=CC(C=2C=3C=CNC=3N=CC=2)=C1 VXZHVNJQMHZXJB-UHFFFAOYSA-N 0.000 description 2
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- HGLJGFMGEOLFQL-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,3-b]pyridine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C2=NC=CC(B3OC(C)(C)C(C)(C)O3)=C2C=C1 HGLJGFMGEOLFQL-UHFFFAOYSA-N 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- CIOGKEKLFQEUEW-UHFFFAOYSA-N 2-methyl-2-[6-(1h-pyrrolo[2,3-b]pyridin-4-yl)pyridin-2-yl]propanoic acid Chemical compound OC(=O)C(C)(C)C1=CC=CC(C=2C=3C=CNC=3N=CC=2)=N1 CIOGKEKLFQEUEW-UHFFFAOYSA-N 0.000 description 2
- HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 description 2
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- KSNKQSPJFRQSEI-UHFFFAOYSA-N 3,3,3-trifluoropropanoic acid Chemical compound OC(=O)CC(F)(F)F KSNKQSPJFRQSEI-UHFFFAOYSA-N 0.000 description 2
- VGNHHTGFRGNITJ-UHFFFAOYSA-N 3-(1h-pyrrolo[2,3-b]pyridin-4-yl)benzoic acid Chemical compound OC(=O)C1=CC=CC(C=2C=3C=CNC=3N=CC=2)=C1 VGNHHTGFRGNITJ-UHFFFAOYSA-N 0.000 description 2
- LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- LZPWAYBEOJRFAX-UHFFFAOYSA-N 4,4,5,5-tetramethyl-1,3,2$l^{2}-dioxaborolane Chemical compound CC1(C)O[B]OC1(C)C LZPWAYBEOJRFAX-UHFFFAOYSA-N 0.000 description 2
- SZLYEAYUTZPHRC-UHFFFAOYSA-N 4-(3,4-dimethoxyphenyl)-1h-pyrrolo[2,3-b]pyridine Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC=NC2=C1C=CN2 SZLYEAYUTZPHRC-UHFFFAOYSA-N 0.000 description 2
- JBCGESKLOMWSNG-UHFFFAOYSA-N 4-(5-chloro-1h-pyrrolo[2,3-b]pyridin-4-yl)-1h-pyrrole-2-carboxylic acid Chemical compound N1C(C(=O)O)=CC(C=2C=3C=CNC=3N=CC=2Cl)=C1 JBCGESKLOMWSNG-UHFFFAOYSA-N 0.000 description 2
- QWANCYQFZTZHTP-UHFFFAOYSA-N 4-(6-fluoropyridin-2-yl)-1-(4-methylphenyl)sulfonylpyrrolo[2,3-b]pyridine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C2=NC=CC(C=3N=C(F)C=CC=3)=C2C=C1 QWANCYQFZTZHTP-UHFFFAOYSA-N 0.000 description 2
- ABNQLMHYRYVUFU-UHFFFAOYSA-N 4-[3-[(4-methylpiperazin-1-yl)methyl]phenyl]-1h-pyrrolo[2,3-b]pyridine Chemical compound C1CN(C)CCN1CC1=CC=CC(C=2C=3C=CNC=3N=CC=2)=C1 ABNQLMHYRYVUFU-UHFFFAOYSA-N 0.000 description 2
- NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical class NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 description 2
- PDONIKHDXYHTLS-UHFFFAOYSA-N 4-bromothiophene-2-carbaldehyde Chemical compound BrC1=CSC(C=O)=C1 PDONIKHDXYHTLS-UHFFFAOYSA-N 0.000 description 2
- HJZFPRVFLBBAMU-UHFFFAOYSA-N 4-bromothiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC(Br)=CS1 HJZFPRVFLBBAMU-UHFFFAOYSA-N 0.000 description 2
- CZVWOOHCZDZJRQ-UHFFFAOYSA-N 5-chloro-4-(1h-pyrazol-4-yl)-1h-pyrrolo[2,3-b]pyridine Chemical compound ClC1=CN=C2NC=CC2=C1C=1C=NNC=1 CZVWOOHCZDZJRQ-UHFFFAOYSA-N 0.000 description 2
- WGGIODDRZRZHCC-UHFFFAOYSA-N 5-chloro-n-cyclohexyl-1h-pyrrolo[2,3-b]pyridin-4-amine Chemical compound ClC1=CN=C2NC=CC2=C1NC1CCCCC1 WGGIODDRZRZHCC-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- 208000014997 Crohn colitis Diseases 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 239000004705 High-molecular-weight polyethylene Substances 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 108010005716 Interferon beta-1a Proteins 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- KNUWGCRHJSDELT-UHFFFAOYSA-N ON(C=CC1=C2)C1=NC=C2Cl Chemical compound ON(C=CC1=C2)C1=NC=C2Cl KNUWGCRHJSDELT-UHFFFAOYSA-N 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- 239000004264 Petrolatum Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 2
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 2
- 101710140204 Signal transducer and transcription activator Proteins 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- 206010045240 Type I hypersensitivity Diseases 0.000 description 2
- XVAHGAURKGYVSG-UHFFFAOYSA-N [3-[1-(4-methylphenyl)sulfonylpyrrolo[2,3-b]pyridin-4-yl]phenyl]methanol Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C2=NC=CC(C=3C=C(CO)C=CC=3)=C2C=C1 XVAHGAURKGYVSG-UHFFFAOYSA-N 0.000 description 2
- 235000010419 agar Nutrition 0.000 description 2
- 239000000783 alginic acid Substances 0.000 description 2
- 229960001126 alginic acid Drugs 0.000 description 2
- 150000004781 alginic acids Chemical class 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 150000003862 amino acid derivatives Chemical class 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 239000002246 antineoplastic agent Substances 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000005160 aryl oxy alkyl group Chemical group 0.000 description 2
- 125000005334 azaindolyl group Chemical class N1N=C(C2=CC=CC=C12)* 0.000 description 2
- DCBDOYDVQJVXOH-UHFFFAOYSA-N azane;1h-indole Chemical compound N.C1=CC=C2NC=CC2=C1 DCBDOYDVQJVXOH-UHFFFAOYSA-N 0.000 description 2
- 229960002170 azathioprine Drugs 0.000 description 2
- LMEKQMALGUDUQG-UHFFFAOYSA-N azathioprine Chemical compound CN1C=NC([N+]([O-])=O)=C1SC1=NC=NC2=C1NC=N2 LMEKQMALGUDUQG-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 229920002988 biodegradable polymer Polymers 0.000 description 2
- 239000004621 biodegradable polymer Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 235000012343 cottonseed oil Nutrition 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 239000013058 crude material Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- SVPZJHKVRMRREG-UHFFFAOYSA-N cyclopentanecarbonitrile Chemical compound N#CC1CCCC1 SVPZJHKVRMRREG-UHFFFAOYSA-N 0.000 description 2
- 229940127089 cytotoxic agent Drugs 0.000 description 2
- UXGNZZKBCMGWAZ-UHFFFAOYSA-N dimethylformamide dmf Chemical compound CN(C)C=O.CN(C)C=O UXGNZZKBCMGWAZ-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 2
- 229940043264 dodecyl sulfate Drugs 0.000 description 2
- ADEBPBSSDYVVLD-UHFFFAOYSA-N donepezil Chemical compound O=C1C=2C=C(OC)C(OC)=CC=2CC1CC(CC1)CCN1CC1=CC=CC=C1 ADEBPBSSDYVVLD-UHFFFAOYSA-N 0.000 description 2
- 239000008298 dragée Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 230000001804 emulsifying effect Effects 0.000 description 2
- 239000003623 enhancer Substances 0.000 description 2
- 238000009505 enteric coating Methods 0.000 description 2
- 239000002702 enteric coating Substances 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- MMXKVMNBHPAILY-UHFFFAOYSA-N ethyl laurate Chemical compound CCCCCCCCCCCC(=O)OCC MMXKVMNBHPAILY-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 238000004401 flow injection analysis Methods 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 125000005456 glyceride group Chemical group 0.000 description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- 125000004475 heteroaralkyl group Chemical group 0.000 description 2
- 125000005114 heteroarylalkoxy group Chemical group 0.000 description 2
- 239000003906 humectant Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 230000028993 immune response Effects 0.000 description 2
- 229940102223 injectable solution Drugs 0.000 description 2
- 229940102213 injectable suspension Drugs 0.000 description 2
- ZRKSVHFXTRFQFL-UHFFFAOYSA-N isocyanomethane Chemical compound C[N+]#[C-] ZRKSVHFXTRFQFL-UHFFFAOYSA-N 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000008297 liquid dosage form Substances 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 229910001629 magnesium chloride Inorganic materials 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- IZDROVVXIHRYMH-UHFFFAOYSA-N methanesulfonic anhydride Chemical compound CS(=O)(=O)OS(C)(=O)=O IZDROVVXIHRYMH-UHFFFAOYSA-N 0.000 description 2
- OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 2
- 239000004530 micro-emulsion Substances 0.000 description 2
- 235000013336 milk Nutrition 0.000 description 2
- 239000008267 milk Substances 0.000 description 2
- 210000004080 milk Anatomy 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- FCZAIJMGROGYMW-UHFFFAOYSA-N morpholin-4-yl-[3-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methanone Chemical compound C=1C=CC(C=2C=3C=CNC=3N=CC=2)=CC=1C(=O)N1CCOCC1 FCZAIJMGROGYMW-UHFFFAOYSA-N 0.000 description 2
- DFOSXJAYPNNXPZ-UHFFFAOYSA-N n,n-dimethyl-1-[3-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methanamine Chemical compound CN(C)CC1=CC=CC(C=2C=3C=CNC=3N=CC=2)=C1 DFOSXJAYPNNXPZ-UHFFFAOYSA-N 0.000 description 2
- GFVIUKUNDPIDFP-UHFFFAOYSA-N n-[6-(1h-pyrrolo[2,3-b]pyridin-4-yl)pyridin-2-yl]benzamide Chemical compound C=1C=CC(C=2C=3C=CNC=3N=CC=2)=NC=1NC(=O)C1=CC=CC=C1 GFVIUKUNDPIDFP-UHFFFAOYSA-N 0.000 description 2
- QYZQIWCUBKCSDD-UHFFFAOYSA-N n-methyl-3-(1h-pyrrolo[2,3-b]pyridin-4-yl)benzamide Chemical compound CNC(=O)C1=CC=CC(C=2C=3C=CNC=3N=CC=2)=C1 QYZQIWCUBKCSDD-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 231100000344 non-irritating Toxicity 0.000 description 2
- 239000000346 nonvolatile oil Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 229940066842 petrolatum Drugs 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- ULUADKXZJBCXKV-UHFFFAOYSA-N piperidin-1-yl-[3-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methanone Chemical compound C=1C=CC(C=2C=3C=CNC=3N=CC=2)=CC=1C(=O)N1CCCCC1 ULUADKXZJBCXKV-UHFFFAOYSA-N 0.000 description 2
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 2
- 235000011181 potassium carbonates Nutrition 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 210000002307 prostate Anatomy 0.000 description 2
- 125000006239 protecting group Chemical class 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- 125000002098 pyridazinyl group Chemical group 0.000 description 2
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 2
- 238000005956 quaternization reaction Methods 0.000 description 2
- 210000000664 rectum Anatomy 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 108010041788 rho-Associated Kinases Proteins 0.000 description 2
- 102000000568 rho-Associated Kinases Human genes 0.000 description 2
- 239000012047 saturated solution Substances 0.000 description 2
- 239000008159 sesame oil Substances 0.000 description 2
- 235000011803 sesame oil Nutrition 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 2
- 239000008279 sol Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- AKQXKEBCONUWCL-UHFFFAOYSA-N tert-butyl 3-aminopiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC(N)C1 AKQXKEBCONUWCL-UHFFFAOYSA-N 0.000 description 2
- CMIBWIAICVBURI-UHFFFAOYSA-N tert-butyl 3-aminopyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(N)C1 CMIBWIAICVBURI-UHFFFAOYSA-N 0.000 description 2
- 125000004001 thioalkyl group Chemical group 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 description 1
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 1
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 1
- ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 1
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 1
- GCTFTMWXZFLTRR-GFCCVEGCSA-N (2r)-2-amino-n-[3-(difluoromethoxy)-4-(1,3-oxazol-5-yl)phenyl]-4-methylpentanamide Chemical compound FC(F)OC1=CC(NC(=O)[C@H](N)CC(C)C)=CC=C1C1=CN=CO1 GCTFTMWXZFLTRR-GFCCVEGCSA-N 0.000 description 1
- IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 description 1
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 description 1
- QVHJQCGUWFKTSE-YFKPBYRVSA-N (2s)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound OC(=O)[C@H](C)NC(=O)OC(C)(C)C QVHJQCGUWFKTSE-YFKPBYRVSA-N 0.000 description 1
- VIJSPAIQWVPKQZ-BLECARSGSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-4-methylpentanoyl]amino]-4,4-dimethylpentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(C)=O VIJSPAIQWVPKQZ-BLECARSGSA-N 0.000 description 1
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 1
- HUMQBXRKDQYSTI-VKHMYHEASA-N (2s)-2-amino-n-(2,2,2-trifluoroethyl)propanamide Chemical compound C[C@H](N)C(=O)NCC(F)(F)F HUMQBXRKDQYSTI-VKHMYHEASA-N 0.000 description 1
- ULCISHRACFRKQI-ZDUSSCGKSA-N (2s)-4-methyl-2-[[6-(1h-pyrrolo[2,3-b]pyridin-4-yl)pyridin-2-yl]amino]pentan-1-ol Chemical compound CC(C)C[C@@H](CO)NC1=CC=CC(C=2C=3C=CNC=3N=CC=2)=N1 ULCISHRACFRKQI-ZDUSSCGKSA-N 0.000 description 1
- STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 description 1
- RCVDPBFUMYUKPB-UHFFFAOYSA-N (3,4-dimethoxyphenyl)boronic acid Chemical compound COC1=CC=C(B(O)O)C=C1OC RCVDPBFUMYUKPB-UHFFFAOYSA-N 0.000 description 1
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 1
- UDQTXCHQKHIQMH-KYGLGHNPSA-N (3ar,5s,6s,7r,7ar)-5-(difluoromethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](C(F)F)[C@@H](O)[C@@H]2O UDQTXCHQKHIQMH-KYGLGHNPSA-N 0.000 description 1
- HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 description 1
- MPDDTAJMJCESGV-CTUHWIOQSA-M (3r,5r)-7-[2-(4-fluorophenyl)-5-[methyl-[(1r)-1-phenylethyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoate Chemical compound C1([C@@H](C)N(C)C(=O)C2=NN(C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C2C(C)C)C=2C=CC(F)=CC=2)=CC=CC=C1 MPDDTAJMJCESGV-CTUHWIOQSA-M 0.000 description 1
- YQOLEILXOBUDMU-KRWDZBQOSA-N (4R)-5-[(6-bromo-3-methyl-2-pyrrolidin-1-ylquinoline-4-carbonyl)amino]-4-(2-chlorophenyl)pentanoic acid Chemical compound CC1=C(C2=C(C=CC(=C2)Br)N=C1N3CCCC3)C(=O)NC[C@H](CCC(=O)O)C4=CC=CC=C4Cl YQOLEILXOBUDMU-KRWDZBQOSA-N 0.000 description 1
- STPKWKPURVSAJF-LJEWAXOPSA-N (4r,5r)-5-[4-[[4-(1-aza-4-azoniabicyclo[2.2.2]octan-4-ylmethyl)phenyl]methoxy]phenyl]-3,3-dibutyl-7-(dimethylamino)-1,1-dioxo-4,5-dihydro-2h-1$l^{6}-benzothiepin-4-ol Chemical compound O[C@H]1C(CCCC)(CCCC)CS(=O)(=O)C2=CC=C(N(C)C)C=C2[C@H]1C(C=C1)=CC=C1OCC(C=C1)=CC=C1C[N+]1(CC2)CCN2CC1 STPKWKPURVSAJF-LJEWAXOPSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- DEVSOMFAQLZNKR-RJRFIUFISA-N (z)-3-[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-triazol-1-yl]-n'-pyrazin-2-ylprop-2-enehydrazide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C2=NN(\C=C/C(=O)NNC=3N=CC=NC=3)C=N2)=C1 DEVSOMFAQLZNKR-RJRFIUFISA-N 0.000 description 1
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 description 1
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 description 1
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 description 1
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 description 1
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 description 1
- 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 description 1
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 description 1
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 description 1
- 229940058015 1,3-butylene glycol Drugs 0.000 description 1
- AICIYIDUYNFPRY-UHFFFAOYSA-N 1,3-dihydro-2H-imidazol-2-one Chemical compound O=C1NC=CN1 AICIYIDUYNFPRY-UHFFFAOYSA-N 0.000 description 1
- KKHFRAFPESRGGD-UHFFFAOYSA-N 1,3-dimethyl-7-[3-(n-methylanilino)propyl]purine-2,6-dione Chemical compound C1=NC=2N(C)C(=O)N(C)C(=O)C=2N1CCCN(C)C1=CC=CC=C1 KKHFRAFPESRGGD-UHFFFAOYSA-N 0.000 description 1
- SBADDAMKZPLPNU-UHFFFAOYSA-N 1-(6-chloropyridin-2-yl)cyclohexane-1-carbonitrile Chemical compound ClC1=CC=CC(C2(CCCCC2)C#N)=N1 SBADDAMKZPLPNU-UHFFFAOYSA-N 0.000 description 1
- WRGUAFTXDCJCGC-UHFFFAOYSA-N 1-(6-chloropyridin-2-yl)cyclopropane-1-carbonitrile Chemical compound ClC1=CC=CC(C2(CC2)C#N)=N1 WRGUAFTXDCJCGC-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 1
- WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 1
- PWCQEEDSPHKPHP-UHFFFAOYSA-N 1-[4-[6-(1h-pyrrolo[2,3-b]pyridin-4-yl)pyridin-2-yl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1C1=CC=CC(C=2C=3C=CNC=3N=CC=2)=N1 PWCQEEDSPHKPHP-UHFFFAOYSA-N 0.000 description 1
- BZLLPBPVGXCCKN-UHFFFAOYSA-N 1-[4-[6-(5-chloro-1h-pyrrolo[2,3-b]pyridin-4-yl)pyridin-2-yl]-1,4-diazepan-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCCN1C1=CC=CC(C=2C=3C=CNC=3N=CC=2Cl)=N1 BZLLPBPVGXCCKN-UHFFFAOYSA-N 0.000 description 1
- VHKBEKUYQZRSRU-UHFFFAOYSA-N 1-[6-(1h-pyrrolo[2,3-b]pyridin-4-yl)pyridin-2-yl]-2,3-dihydropyrrol-4-ol Chemical compound C1CC(O)=CN1C1=CC=CC(C=2C=3C=CNC=3N=CC=2)=N1 VHKBEKUYQZRSRU-UHFFFAOYSA-N 0.000 description 1
- IELJAALOOAWUPT-UHFFFAOYSA-N 1-[6-(1h-pyrrolo[2,3-b]pyridin-4-yl)pyridin-2-yl]cyclohexane-1-carbonitrile Chemical compound C=1C=CC(C=2C=3C=CNC=3N=CC=2)=NC=1C1(C#N)CCCCC1 IELJAALOOAWUPT-UHFFFAOYSA-N 0.000 description 1
- KPQXYCILDCNQPX-UHFFFAOYSA-N 1-[6-(1h-pyrrolo[2,3-b]pyridin-4-yl)pyridin-2-yl]cyclopentane-1-carbonitrile Chemical compound C=1C=CC(C=2C=3C=CNC=3N=CC=2)=NC=1C1(C#N)CCCC1 KPQXYCILDCNQPX-UHFFFAOYSA-N 0.000 description 1
- WBSPYJVCMMKCHN-UHFFFAOYSA-N 1-[6-(1h-pyrrolo[2,3-b]pyridin-4-yl)pyridin-2-yl]cyclopropane-1-carbonitrile Chemical compound C=1C=CC(C=2C=3C=CNC=3N=CC=2)=NC=1C1(C#N)CC1 WBSPYJVCMMKCHN-UHFFFAOYSA-N 0.000 description 1
- QDNOVIAAFXATGF-UHFFFAOYSA-N 1-[6-[1-(4-methylphenyl)sulfonylpyrrolo[2,3-b]pyridin-4-yl]pyridin-2-yl]cyclopropane-1-carbonitrile Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C2=NC=CC(C=3N=C(C=CC=3)C3(CC3)C#N)=C2C=C1 QDNOVIAAFXATGF-UHFFFAOYSA-N 0.000 description 1
- QXOGPTXQGKQSJT-UHFFFAOYSA-N 1-amino-4-[4-(3,4-dimethylphenyl)sulfanylanilino]-9,10-dioxoanthracene-2-sulfonic acid Chemical compound Cc1ccc(Sc2ccc(Nc3cc(c(N)c4C(=O)c5ccccc5C(=O)c34)S(O)(=O)=O)cc2)cc1C QXOGPTXQGKQSJT-UHFFFAOYSA-N 0.000 description 1
- MEHBOHFZFXGIQL-UHFFFAOYSA-N 1-ethylcyclohexane-1-carbonitrile Chemical compound CCC1(C#N)CCCCC1 MEHBOHFZFXGIQL-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
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 1
- DGHHQBMTXTWTJV-BQAIUKQQSA-N 119413-54-6 Chemical compound Cl.C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 DGHHQBMTXTWTJV-BQAIUKQQSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- MJLXGUSURNOWEH-UHFFFAOYSA-N 2,2-dimethyl-3-[[6-(1h-pyrrolo[2,3-b]pyridin-4-yl)pyridin-2-yl]amino]propan-1-ol Chemical compound OCC(C)(C)CNC1=CC=CC(C=2C=3C=CNC=3N=CC=2)=N1 MJLXGUSURNOWEH-UHFFFAOYSA-N 0.000 description 1
- YJUFGFXVASPYFQ-UHFFFAOYSA-N 2,3-dihydro-1-benzothiophene Chemical compound C1=CC=C2SCCC2=C1 YJUFGFXVASPYFQ-UHFFFAOYSA-N 0.000 description 1
- CHHHXKFHOYLYRE-UHFFFAOYSA-M 2,4-Hexadienoic acid, potassium salt (1:1), (2E,4E)- Chemical compound [K+].CC=CC=CC([O-])=O CHHHXKFHOYLYRE-UHFFFAOYSA-M 0.000 description 1
- BTTNYQZNBZNDOR-UHFFFAOYSA-N 2,4-dichloropyrimidine Chemical compound ClC1=CC=NC(Cl)=N1 BTTNYQZNBZNDOR-UHFFFAOYSA-N 0.000 description 1
- FILKGCRCWDMBKA-UHFFFAOYSA-N 2,6-dichloropyridine Chemical compound ClC1=CC=CC(Cl)=N1 FILKGCRCWDMBKA-UHFFFAOYSA-N 0.000 description 1
- VCUXVXLUOHDHKK-UHFFFAOYSA-N 2-(2-aminopyrimidin-4-yl)-4-(2-chloro-4-methoxyphenyl)-1,3-thiazole-5-carboxamide Chemical compound ClC1=CC(OC)=CC=C1C1=C(C(N)=O)SC(C=2N=C(N)N=CC=2)=N1 VCUXVXLUOHDHKK-UHFFFAOYSA-N 0.000 description 1
- QEBYEVQKHRUYPE-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-[(1-methylpyrazol-3-yl)methyl]-4-[[methyl(pyridin-3-ylmethyl)amino]methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1=CN(C)N=C1CN1C(=O)C=C2NN(C=3C(=CC=CC=3)Cl)C(=O)C2=C1CN(C)CC1=CC=CN=C1 QEBYEVQKHRUYPE-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- ADSCNOMKFNDGCD-UHFFFAOYSA-N 2-[3-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]acetonitrile Chemical compound N#CCC1=CC=CC(C=2C=3C=CNC=3N=CC=2)=C1 ADSCNOMKFNDGCD-UHFFFAOYSA-N 0.000 description 1
- WUVKRUYSADCTLD-UHFFFAOYSA-N 2-[6-(1h-pyrrolo[2,3-b]pyridin-4-yl)pyridin-2-yl]propan-2-ol Chemical compound CC(C)(O)C1=CC=CC(C=2C=3C=CNC=3N=CC=2)=N1 WUVKRUYSADCTLD-UHFFFAOYSA-N 0.000 description 1
- FMKGJQHNYMWDFJ-CVEARBPZSA-N 2-[[4-(2,2-difluoropropoxy)pyrimidin-5-yl]methylamino]-4-[[(1R,4S)-4-hydroxy-3,3-dimethylcyclohexyl]amino]pyrimidine-5-carbonitrile Chemical compound FC(COC1=NC=NC=C1CNC1=NC=C(C(=N1)N[C@H]1CC([C@H](CC1)O)(C)C)C#N)(C)F FMKGJQHNYMWDFJ-CVEARBPZSA-N 0.000 description 1
- OODHMYDSJTXUPO-UHFFFAOYSA-N 2-[methyl-[6-(1h-pyrrolo[2,3-b]pyridin-4-yl)pyridin-2-yl]amino]-1-phenylethanol Chemical compound C=1C=CC(C=2C=3C=CNC=3N=CC=2)=NC=1N(C)CC(O)C1=CC=CC=C1 OODHMYDSJTXUPO-UHFFFAOYSA-N 0.000 description 1
- YDYGQNPXKHXVCS-UHFFFAOYSA-N 2-[methyl-[6-(1h-pyrrolo[2,3-b]pyridin-4-yl)pyridin-2-yl]amino]ethanol Chemical compound OCCN(C)C1=CC=CC(C=2C=3C=CNC=3N=CC=2)=N1 YDYGQNPXKHXVCS-UHFFFAOYSA-N 0.000 description 1
- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 1
- TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 1
- JCBPETKZIGVZRE-UHFFFAOYSA-N 2-aminobutan-1-ol Chemical compound CCC(N)CO JCBPETKZIGVZRE-UHFFFAOYSA-N 0.000 description 1
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 1
- KQPQXZDIPWYWJO-UHFFFAOYSA-N 2-bromo-5-methoxythiophene Chemical compound COC1=CC=C(Br)S1 KQPQXZDIPWYWJO-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- LFOIDLOIBZFWDO-UHFFFAOYSA-N 2-methoxy-6-[6-methoxy-4-[(3-phenylmethoxyphenyl)methoxy]-1-benzofuran-2-yl]imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=C2SC(OC)=NN2C=C1C(OC1=CC(OC)=C2)=CC1=C2OCC(C=1)=CC=CC=1OCC1=CC=CC=C1 LFOIDLOIBZFWDO-UHFFFAOYSA-N 0.000 description 1
- 229940080296 2-naphthalenesulfonate Drugs 0.000 description 1
- LEACJMVNYZDSKR-UHFFFAOYSA-N 2-octyldodecan-1-ol Chemical compound CCCCCCCCCCC(CO)CCCCCCCC LEACJMVNYZDSKR-UHFFFAOYSA-N 0.000 description 1
- ZZVOSCQKWZSUMZ-UHFFFAOYSA-N 2-phenyl-n-[6-(1h-pyrrolo[2,3-b]pyridin-4-yl)pyridin-2-yl]acetamide Chemical compound C=1C=CC(C=2C=3C=CNC=3N=CC=2)=NC=1NC(=O)CC1=CC=CC=C1 ZZVOSCQKWZSUMZ-UHFFFAOYSA-N 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
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- DFRAKBCRUYUFNT-UHFFFAOYSA-N 3,8-dicyclohexyl-2,4,7,9-tetrahydro-[1,3]oxazino[5,6-h][1,3]benzoxazine Chemical compound C1CCCCC1N1CC(C=CC2=C3OCN(C2)C2CCCCC2)=C3OC1 DFRAKBCRUYUFNT-UHFFFAOYSA-N 0.000 description 1
- LFHFBDBZESNWLQ-UHFFFAOYSA-N 3-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenol Chemical compound OC1=CC=CC(C=2C=3C=CNC=3N=CC=2)=C1 LFHFBDBZESNWLQ-UHFFFAOYSA-N 0.000 description 1
- CPCMSNMGEMRMFF-UHFFFAOYSA-N 3-(3,3,3-trifluoropropylamino)propanenitrile Chemical compound FC(F)(F)CCNCCC#N CPCMSNMGEMRMFF-UHFFFAOYSA-N 0.000 description 1
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
- QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 1
- WFOVEDJTASPCIR-UHFFFAOYSA-N 3-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)methylamino]-n-[[2-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1CNC(C=1)=CC=CC=1C(=O)NCC1=CC=CC=C1C(F)(F)F WFOVEDJTASPCIR-UHFFFAOYSA-N 0.000 description 1
- BGAJNPLDJJBRHK-UHFFFAOYSA-N 3-[2-[5-(3-chloro-4-propan-2-yloxyphenyl)-1,3,4-thiadiazol-2-yl]-3-methyl-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl]propanoic acid Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=NN=C(N2C(=C3CN(CCC(O)=O)CCC3=N2)C)S1 BGAJNPLDJJBRHK-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- ZRPLANDPDWYOMZ-UHFFFAOYSA-N 3-cyclopentylpropionic acid Chemical compound OC(=O)CCC1CCCC1 ZRPLANDPDWYOMZ-UHFFFAOYSA-N 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-M 3-phenylpropionate Chemical compound [O-]C(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-M 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])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
- CLIUIBOBZMLQAZ-UHFFFAOYSA-N 4-(1-benzofuran-4-yl)-1h-pyrrolo[2,3-b]pyridine Chemical compound C1=CN=C2NC=CC2=C1C1=CC=CC2=C1C=CO2 CLIUIBOBZMLQAZ-UHFFFAOYSA-N 0.000 description 1
- VHCADWPCAZCNJX-UHFFFAOYSA-N 4-(2-chloropyridin-4-yl)-1h-pyrrolo[2,3-b]pyridine Chemical compound C1=NC(Cl)=CC(C=2C=3C=CNC=3N=CC=2)=C1 VHCADWPCAZCNJX-UHFFFAOYSA-N 0.000 description 1
- KUUUESUFIZUTKO-UHFFFAOYSA-N 4-(3,4,5-trimethoxyphenyl)-1h-pyrrolo[2,3-b]pyridine Chemical compound COC1=C(OC)C(OC)=CC(C=2C=3C=CNC=3N=CC=2)=C1 KUUUESUFIZUTKO-UHFFFAOYSA-N 0.000 description 1
- ZPJNCAVQKYCAMK-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-1h-pyrrolo[2,3-b]pyridine Chemical compound C1=C(Cl)C(Cl)=CC=C1C1=CC=NC2=C1C=CN2 ZPJNCAVQKYCAMK-UHFFFAOYSA-N 0.000 description 1
- CAKKWSHZBOSGPV-UHFFFAOYSA-N 4-(3,5-dimethylphenyl)-1h-pyrrolo[2,3-b]pyridine Chemical compound CC1=CC(C)=CC(C=2C=3C=CNC=3N=CC=2)=C1 CAKKWSHZBOSGPV-UHFFFAOYSA-N 0.000 description 1
- CNFVYUOYBOCZKI-UHFFFAOYSA-N 4-(3-methylpyridin-2-yl)-1h-pyrrolo[2,3-b]pyridine Chemical compound CC1=CC=CN=C1C1=CC=NC2=C1C=CN2 CNFVYUOYBOCZKI-UHFFFAOYSA-N 0.000 description 1
- LGAFIKHUDGHRRL-UHFFFAOYSA-N 4-(3-phenylmethoxyphenyl)-1h-pyrrolo[2,3-b]pyridine Chemical compound C=1C=CC(C=2C=3C=CNC=3N=CC=2)=CC=1OCC1=CC=CC=C1 LGAFIKHUDGHRRL-UHFFFAOYSA-N 0.000 description 1
- XFKPGJQKUAFPQN-UHFFFAOYSA-N 4-(4-propan-2-yloxyphenyl)-1h-pyrrolo[2,3-b]pyridine Chemical compound C1=CC(OC(C)C)=CC=C1C1=CC=NC2=C1C=CN2 XFKPGJQKUAFPQN-UHFFFAOYSA-N 0.000 description 1
- MLSKIYXBKZJIDW-UHFFFAOYSA-N 4-(5-fluoro-1h-pyrrolo[2,3-b]pyridin-4-yl)-1h-pyrrole-2-carboxylic acid Chemical compound N1C(C(=O)O)=CC(C=2C=3C=CNC=3N=CC=2F)=C1 MLSKIYXBKZJIDW-UHFFFAOYSA-N 0.000 description 1
- XKBBAXVBCSLAQJ-UHFFFAOYSA-N 4-(6-propan-2-ylpyridin-2-yl)-1h-pyrrolo[2,3-b]pyridine Chemical compound CC(C)C1=CC=CC(C=2C=3C=CNC=3N=CC=2)=N1 XKBBAXVBCSLAQJ-UHFFFAOYSA-N 0.000 description 1
- DSVCSVHVJVAHGM-UHFFFAOYSA-N 4-[3-(chloromethyl)phenyl]-1-(4-methylphenyl)sulfonylpyrrolo[2,3-b]pyridine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C2=NC=CC(C=3C=C(CCl)C=CC=3)=C2C=C1 DSVCSVHVJVAHGM-UHFFFAOYSA-N 0.000 description 1
- BSGNMMWWXAVLPD-UHFFFAOYSA-N 4-[3-(methoxymethyl)phenyl]-1h-pyrrolo[2,3-b]pyridine Chemical compound COCC1=CC=CC(C=2C=3C=CNC=3N=CC=2)=C1 BSGNMMWWXAVLPD-UHFFFAOYSA-N 0.000 description 1
- HRTGYURISCMJRH-UHFFFAOYSA-N 4-[3-(piperidin-1-ylmethyl)phenyl]-1h-pyrrolo[2,3-b]pyridine Chemical compound C=1C=CC(C=2C=3C=CNC=3N=CC=2)=CC=1CN1CCCCC1 HRTGYURISCMJRH-UHFFFAOYSA-N 0.000 description 1
- RJHUSSUXKJXYOM-UHFFFAOYSA-N 4-[6-(3-methylpiperidin-1-yl)pyridin-2-yl]-1h-pyrrolo[2,3-b]pyridine Chemical compound C1C(C)CCCN1C1=CC=CC(C=2C=3C=CNC=3N=CC=2)=N1 RJHUSSUXKJXYOM-UHFFFAOYSA-N 0.000 description 1
- WYFCZWSWFGJODV-MIANJLSGSA-N 4-[[(1s)-2-[(e)-3-[3-chloro-2-fluoro-6-(tetrazol-1-yl)phenyl]prop-2-enoyl]-5-(4-methyl-2-oxopiperazin-1-yl)-3,4-dihydro-1h-isoquinoline-1-carbonyl]amino]benzoic acid Chemical compound O=C1CN(C)CCN1C1=CC=CC2=C1CCN(C(=O)\C=C\C=1C(=CC=C(Cl)C=1F)N1N=NN=C1)[C@@H]2C(=O)NC1=CC=C(C(O)=O)C=C1 WYFCZWSWFGJODV-MIANJLSGSA-N 0.000 description 1
- MPMKMQHJHDHPBE-RUZDIDTESA-N 4-[[(2r)-1-(1-benzothiophene-3-carbonyl)-2-methylazetidine-2-carbonyl]-[(3-chlorophenyl)methyl]amino]butanoic acid Chemical compound O=C([C@@]1(N(CC1)C(=O)C=1C2=CC=CC=C2SC=1)C)N(CCCC(O)=O)CC1=CC=CC(Cl)=C1 MPMKMQHJHDHPBE-RUZDIDTESA-N 0.000 description 1
- VFFGROVGEJYYCV-UHFFFAOYSA-N 4-[[3-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methyl]morpholine Chemical compound C=1C=CC(C=2C=3C=CNC=3N=CC=2)=CC=1CN1CCOCC1 VFFGROVGEJYYCV-UHFFFAOYSA-N 0.000 description 1
- LEZHTYOQWQEBLH-UHFFFAOYSA-N 4-bromo-1h-pyrrolo[2,3-b]pyridine Chemical compound BrC1=CC=NC2=C1C=CN2 LEZHTYOQWQEBLH-UHFFFAOYSA-N 0.000 description 1
- UOUXYCQYVQVYCQ-UHFFFAOYSA-N 4-bromo-5-chloro-1-(4-methylphenyl)sulfonylpyrrolo[2,3-b]pyridine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C2=NC=C(Cl)C(Br)=C2C=C1 UOUXYCQYVQVYCQ-UHFFFAOYSA-N 0.000 description 1
- VTDLIXTUIXEFID-UHFFFAOYSA-N 4-pyridin-3-yl-1h-pyrrolo[2,3-b]pyridine Chemical compound C1=CN=C2NC=CC2=C1C1=CC=CN=C1 VTDLIXTUIXEFID-UHFFFAOYSA-N 0.000 description 1
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 description 1
- JZLJKFICWUITIH-UHFFFAOYSA-N 4-thiophen-3-yl-1h-pyrrolo[2,3-b]pyridine Chemical compound C1=CN=C2NC=CC2=C1C=1C=CSC=1 JZLJKFICWUITIH-UHFFFAOYSA-N 0.000 description 1
- VKLKXFOZNHEBSW-UHFFFAOYSA-N 5-[[3-[(4-morpholin-4-ylbenzoyl)amino]phenyl]methoxy]pyridine-3-carboxamide Chemical compound O1CCN(CC1)C1=CC=C(C(=O)NC=2C=C(COC=3C=NC=C(C(=O)N)C=3)C=CC=2)C=C1 VKLKXFOZNHEBSW-UHFFFAOYSA-N 0.000 description 1
- MLAKVXOLMDBAET-UHFFFAOYSA-N 5-chloro-4-(6-pyrrolidin-1-ylpyridin-2-yl)-1h-pyrrolo[2,3-b]pyridine Chemical compound ClC1=CN=C2NC=CC2=C1C(N=1)=CC=CC=1N1CCCC1 MLAKVXOLMDBAET-UHFFFAOYSA-N 0.000 description 1
- 125000006163 5-membered heteroaryl group Chemical group 0.000 description 1
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 description 1
- RINYAJWOECFCNW-UHFFFAOYSA-N 6-(5-chloro-1h-pyrrolo[2,3-b]pyridin-4-yl)-n-(2-methylpropyl)pyridin-2-amine Chemical compound CC(C)CNC1=CC=CC(C=2C=3C=CNC=3N=CC=2Cl)=N1 RINYAJWOECFCNW-UHFFFAOYSA-N 0.000 description 1
- LBIDTLCDDUHATK-UHFFFAOYSA-N 6-(5-chloro-1h-pyrrolo[2,3-b]pyridin-4-yl)-n-cyclopentylpyridin-2-amine Chemical compound ClC1=CN=C2NC=CC2=C1C(N=1)=CC=CC=1NC1CCCC1 LBIDTLCDDUHATK-UHFFFAOYSA-N 0.000 description 1
- QVJDIGLZFCZAKK-UHFFFAOYSA-N 6-[1-(4-methylphenyl)sulfonylpyrrolo[2,3-b]pyridin-4-yl]pyridin-2-amine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C2=NC=CC(C=3N=C(N)C=CC=3)=C2C=C1 QVJDIGLZFCZAKK-UHFFFAOYSA-N 0.000 description 1
- GDUANFXPOZTYKS-UHFFFAOYSA-N 6-bromo-8-[(2,6-difluoro-4-methoxybenzoyl)amino]-4-oxochromene-2-carboxylic acid Chemical compound FC1=CC(OC)=CC(F)=C1C(=O)NC1=CC(Br)=CC2=C1OC(C(O)=O)=CC2=O GDUANFXPOZTYKS-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
- HCCNBKFJYUWLEX-UHFFFAOYSA-N 7-(6-methoxypyridin-3-yl)-1-(2-propoxyethyl)-3-(pyrazin-2-ylmethylamino)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1NCC1=CN=CC=N1 HCCNBKFJYUWLEX-UHFFFAOYSA-N 0.000 description 1
- XASOHFCUIQARJT-UHFFFAOYSA-N 8-methoxy-6-[7-(2-morpholin-4-ylethoxy)imidazo[1,2-a]pyridin-3-yl]-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-one Chemical compound C(N1C(=O)C2=C(OC)C=C(C=3N4C(=NC=3)C=C(C=C4)OCCN3CCOCC3)C=C2CC1)C(F)(F)F XASOHFCUIQARJT-UHFFFAOYSA-N 0.000 description 1
- IRBAWVGZNJIROV-SFHVURJKSA-N 9-(2-cyclopropylethynyl)-2-[[(2s)-1,4-dioxan-2-yl]methoxy]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(C#CC4CC4)C=C3CCN2C(=O)N=C1OC[C@@H]1COCCO1 IRBAWVGZNJIROV-SFHVURJKSA-N 0.000 description 1
- 239000005541 ACE inhibitor Substances 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 208000037398 BCR-ABL1 negative atypical chronic myeloid leukemia Diseases 0.000 description 1
- IYHHRZBKXXKDDY-UHFFFAOYSA-N BI-605906 Chemical compound N=1C=2SC(C(N)=O)=C(N)C=2C(C(F)(F)CC)=CC=1N1CCC(S(C)(=O)=O)CC1 IYHHRZBKXXKDDY-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 108010017384 Blood Proteins Proteins 0.000 description 1
- 102000004506 Blood Proteins Human genes 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 208000003174 Brain Neoplasms Diseases 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- 238000007125 Buchwald synthesis reaction Methods 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
- UHNRLQRZRNKOKU-UHFFFAOYSA-N CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O Chemical compound CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O UHNRLQRZRNKOKU-UHFFFAOYSA-N 0.000 description 1
- BQXUPNKLZNSUMC-YUQWMIPFSA-N CCN(CCCCCOCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](C)c1ccc(cc1)-c1scnc1C)C(C)(C)C)CCOc1ccc(cc1)C(=O)c1c(sc2cc(O)ccc12)-c1ccc(O)cc1 Chemical compound CCN(CCCCCOCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](C)c1ccc(cc1)-c1scnc1C)C(C)(C)C)CCOc1ccc(cc1)C(=O)c1c(sc2cc(O)ccc12)-c1ccc(O)cc1 BQXUPNKLZNSUMC-YUQWMIPFSA-N 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- BFGAFFLWOFDLEB-UHFFFAOYSA-N CNC1=NC=CC=C1CCN(C)C Chemical compound CNC1=NC=CC=C1CCN(C)C BFGAFFLWOFDLEB-UHFFFAOYSA-N 0.000 description 1
- PKMUHQIDVVOXHQ-HXUWFJFHSA-N C[C@H](C1=CC(C2=CC=C(CNC3CCCC3)S2)=CC=C1)NC(C1=C(C)C=CC(NC2CNC2)=C1)=O Chemical compound C[C@H](C1=CC(C2=CC=C(CNC3CCCC3)S2)=CC=C1)NC(C1=C(C)C=CC(NC2CNC2)=C1)=O PKMUHQIDVVOXHQ-HXUWFJFHSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229940127291 Calcium channel antagonist Drugs 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229920001268 Cholestyramine Polymers 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
- 240000004307 Citrus medica Species 0.000 description 1
- 206010009944 Colon cancer Diseases 0.000 description 1
- 229940126639 Compound 33 Drugs 0.000 description 1
- 229940127007 Compound 39 Drugs 0.000 description 1
- 241001012960 Cropia minthe Species 0.000 description 1
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-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
- 108010036949 Cyclosporine Proteins 0.000 description 1
- 108090000695 Cytokines Proteins 0.000 description 1
- 102000004127 Cytokines Human genes 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- 102100030011 Endoribonuclease Human genes 0.000 description 1
- 101710199605 Endoribonuclease Proteins 0.000 description 1
- 241000792859 Enema Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 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
- 108010010803 Gelatin Proteins 0.000 description 1
- 241000206672 Gelidium Species 0.000 description 1
- 108010072051 Glatiramer Acetate Proteins 0.000 description 1
- 206010018338 Glioma Diseases 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 108010051975 Glycogen Synthase Kinase 3 beta Proteins 0.000 description 1
- 102100038104 Glycogen synthase kinase-3 beta Human genes 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Polymers OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 101000844245 Homo sapiens Non-receptor tyrosine-protein kinase TYK2 Proteins 0.000 description 1
- 101001059454 Homo sapiens Serine/threonine-protein kinase MARK2 Proteins 0.000 description 1
- 101000997835 Homo sapiens Tyrosine-protein kinase JAK1 Proteins 0.000 description 1
- 108091006905 Human Serum Albumin Proteins 0.000 description 1
- 102000008100 Human Serum Albumin Human genes 0.000 description 1
- 208000001718 Immediate Hypersensitivity Diseases 0.000 description 1
- 108090000467 Interferon-beta Proteins 0.000 description 1
- 102000003996 Interferon-beta Human genes 0.000 description 1
- 108010002352 Interleukin-1 Proteins 0.000 description 1
- 108090000862 Ion Channels Proteins 0.000 description 1
- 102000004310 Ion Channels Human genes 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
- 229940123241 Janus kinase 3 inhibitor Drugs 0.000 description 1
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 1
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 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
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
- 239000005517 L01XE01 - Imatinib Substances 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
- 240000003183 Manihot esculenta Species 0.000 description 1
- 235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- UCHDWCPVSPXUMX-TZIWLTJVSA-N Montelukast Chemical compound CC(C)(O)C1=CC=CC=C1CC[C@H](C=1C=C(\C=C\C=2N=C3C=C(Cl)C=CC3=CC=2)C=CC=1)SCC1(CC(O)=O)CC1 UCHDWCPVSPXUMX-TZIWLTJVSA-N 0.000 description 1
- 102000006386 Myelin Proteins Human genes 0.000 description 1
- 108010083674 Myelin Proteins Proteins 0.000 description 1
- 208000037538 Myelomonocytic Juvenile Leukemia Diseases 0.000 description 1
- LVDRREOUMKACNJ-BKMJKUGQSA-N N-[(2R,3S)-2-(4-chlorophenyl)-1-(1,4-dimethyl-2-oxoquinolin-7-yl)-6-oxopiperidin-3-yl]-2-methylpropane-1-sulfonamide Chemical compound CC(C)CS(=O)(=O)N[C@H]1CCC(=O)N([C@@H]1c1ccc(Cl)cc1)c1ccc2c(C)cc(=O)n(C)c2c1 LVDRREOUMKACNJ-BKMJKUGQSA-N 0.000 description 1
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
- AVYVHIKSFXVDBG-UHFFFAOYSA-N N-benzyl-N-hydroxy-2,2-dimethylbutanamide Chemical compound C(C1=CC=CC=C1)N(C(C(CC)(C)C)=O)O AVYVHIKSFXVDBG-UHFFFAOYSA-N 0.000 description 1
- POFVJRKJJBFPII-UHFFFAOYSA-N N-cyclopentyl-5-[2-[[5-[(4-ethylpiperazin-1-yl)methyl]pyridin-2-yl]amino]-5-fluoropyrimidin-4-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound C1(CCCC1)NC=1SC(=C(N=1)C)C1=NC(=NC=C1F)NC1=NC=C(C=C1)CN1CCN(CC1)CC POFVJRKJJBFPII-UHFFFAOYSA-N 0.000 description 1
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 1
- QOVYHDHLFPKQQG-NDEPHWFRSA-N N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O Chemical compound N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O QOVYHDHLFPKQQG-NDEPHWFRSA-N 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- 102100032028 Non-receptor tyrosine-protein kinase TYK2 Human genes 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- 206010033128 Ovarian cancer Diseases 0.000 description 1
- 206010061535 Ovarian neoplasm Diseases 0.000 description 1
- 229930012538 Paclitaxel Natural products 0.000 description 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 description 1
- 229910002666 PdCl2 Inorganic materials 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229920002732 Polyanhydride Polymers 0.000 description 1
- 229920000954 Polyglycolide Polymers 0.000 description 1
- 229920001710 Polyorthoester Polymers 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 206010060862 Prostate cancer Diseases 0.000 description 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
- 101000729528 Rattus norvegicus Rho-associated protein kinase 2 Proteins 0.000 description 1
- 102100039313 Rho-associated protein kinase 1 Human genes 0.000 description 1
- 101710088411 Rho-associated protein kinase 1 Proteins 0.000 description 1
- 102100039314 Rho-associated protein kinase 2 Human genes 0.000 description 1
- 101710088493 Rho-associated protein kinase 2 Proteins 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
- 235000019485 Safflower oil Nutrition 0.000 description 1
- 206010039491 Sarcoma Diseases 0.000 description 1
- 208000034189 Sclerosis Diseases 0.000 description 1
- 101710113029 Serine/threonine-protein kinase Proteins 0.000 description 1
- 102100028904 Serine/threonine-protein kinase MARK2 Human genes 0.000 description 1
- 102100031206 Serine/threonine-protein kinase N1 Human genes 0.000 description 1
- PNUZDKCDAWUEGK-CYZMBNFOSA-N Sitafloxacin Chemical compound C([C@H]1N)N(C=2C(=C3C(C(C(C(O)=O)=CN3[C@H]3[C@H](C3)F)=O)=CC=2F)Cl)CC11CC1 PNUZDKCDAWUEGK-CYZMBNFOSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 1
- 208000005392 Spasm Diseases 0.000 description 1
- SSZBUIDZHHWXNJ-UHFFFAOYSA-N Stearinsaeure-hexadecylester Natural products CCCCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCCCCCC SSZBUIDZHHWXNJ-UHFFFAOYSA-N 0.000 description 1
- 239000012317 TBTU Substances 0.000 description 1
- QJJXYPPXXYFBGM-LFZNUXCKSA-N Tacrolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1\C=C(/C)[C@@H]1[C@H](C)[C@@H](O)CC(=O)[C@H](CC=C)/C=C(C)/C[C@H](C)C[C@H](OC)[C@H]([C@H](C[C@H]2C)OC)O[C@@]2(O)C(=O)C(=O)N2CCCC[C@H]2C(=O)O1 QJJXYPPXXYFBGM-LFZNUXCKSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- 102100033438 Tyrosine-protein kinase JAK1 Human genes 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
- LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 description 1
- SPXSEZMVRJLHQG-XMMPIXPASA-N [(2R)-1-[[4-[(3-phenylmethoxyphenoxy)methyl]phenyl]methyl]pyrrolidin-2-yl]methanol Chemical compound C(C1=CC=CC=C1)OC=1C=C(OCC2=CC=C(CN3[C@H](CCC3)CO)C=C2)C=CC=1 SPXSEZMVRJLHQG-XMMPIXPASA-N 0.000 description 1
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 1
- SFPIINLBMLIHMY-UHFFFAOYSA-N [3-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methanol Chemical compound OCC1=CC=CC(C=2C=3C=CNC=3N=CC=2)=C1 SFPIINLBMLIHMY-UHFFFAOYSA-N 0.000 description 1
- SZPWXAOBLNYOHY-UHFFFAOYSA-N [C]1=CC=NC2=CC=CC=C12 Chemical group [C]1=CC=NC2=CC=CC=C12 SZPWXAOBLNYOHY-UHFFFAOYSA-N 0.000 description 1
- DZJXKISLUDYJSV-UHFFFAOYSA-N [N].C1CCNC1 Chemical compound [N].C1CCNC1 DZJXKISLUDYJSV-UHFFFAOYSA-N 0.000 description 1
- SMNRFWMNPDABKZ-WVALLCKVSA-N [[(2R,3S,4R,5S)-5-(2,6-dioxo-3H-pyridin-3-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4S,5R,6R)-4-fluoro-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)C2C=CC(=O)NC2=O)[C@H](O)[C@@H](F)[C@@H]1O SMNRFWMNPDABKZ-WVALLCKVSA-N 0.000 description 1
- CTCBPRXHVPZNHB-VQFZJOCSSA-N [[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate;(2r,3r,4s,5r)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O.C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O CTCBPRXHVPZNHB-VQFZJOCSSA-N 0.000 description 1
- SORGEQQSQGNZFI-UHFFFAOYSA-N [azido(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(N=[N+]=[N-])OC1=CC=CC=C1 SORGEQQSQGNZFI-UHFFFAOYSA-N 0.000 description 1
- CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 1
- FYJKEHKQUPSJDH-UHFFFAOYSA-N [dimethyl-(trimethylsilylamino)silyl]methane;potassium Chemical compound [K].C[Si](C)(C)N[Si](C)(C)C FYJKEHKQUPSJDH-UHFFFAOYSA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000003655 absorption accelerator Substances 0.000 description 1
- 229940124532 absorption promoter Drugs 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- WEVYAHXRMPXWCK-FIBGUPNXSA-N acetonitrile-d3 Chemical compound [2H]C([2H])([2H])C#N WEVYAHXRMPXWCK-FIBGUPNXSA-N 0.000 description 1
- PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 229940009456 adriamycin Drugs 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 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
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 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
- 229940024606 amino acid Drugs 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 229940082992 antihypertensives mao inhibitors Drugs 0.000 description 1
- 239000000063 antileukemic agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 239000000939 antiparkinson agent Substances 0.000 description 1
- 229940027983 antiseptic and disinfectant quaternary ammonium compound Drugs 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 229940039856 aricept Drugs 0.000 description 1
- 229940072107 ascorbate Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229940009098 aspartate Drugs 0.000 description 1
- XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 description 1
- 208000010216 atopic IgE responsiveness Diseases 0.000 description 1
- 201000004892 atypical chronic myeloid leukemia Diseases 0.000 description 1
- 230000001363 autoimmune Effects 0.000 description 1
- 229940003504 avonex Drugs 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 229960000686 benzalkonium chloride Drugs 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940050390 benzoate Drugs 0.000 description 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 229960002903 benzyl benzoate Drugs 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 description 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
- 239000002876 beta blocker Substances 0.000 description 1
- 229940097320 beta blocking agent Drugs 0.000 description 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-N beta-phenylpropanoic acid Natural products OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 1
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000001574 biopsy Methods 0.000 description 1
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 210000001124 body fluid Anatomy 0.000 description 1
- 239000010839 body fluid Substances 0.000 description 1
- 230000036760 body temperature Effects 0.000 description 1
- 229940098773 bovine serum albumin Drugs 0.000 description 1
- OZVBMTJYIDMWIL-AYFBDAFISA-N bromocriptine Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=C(Br)NC3=C1 OZVBMTJYIDMWIL-AYFBDAFISA-N 0.000 description 1
- 229960002802 bromocriptine Drugs 0.000 description 1
- DQXBYHZEEUGOBF-UHFFFAOYSA-N but-3-enoic acid;ethene Chemical compound C=C.OC(=O)CC=C DQXBYHZEEUGOBF-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 239000000480 calcium channel blocker Substances 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 229960004205 carbidopa Drugs 0.000 description 1
- TZFNLOMSOLWIDK-JTQLQIEISA-N carbidopa (anhydrous) Chemical compound NN[C@@](C(O)=O)(C)CC1=CC=C(O)C(O)=C1 TZFNLOMSOLWIDK-JTQLQIEISA-N 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 229940081733 cetearyl alcohol Drugs 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 229910052729 chemical element Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- 239000000544 cholinesterase inhibitor Substances 0.000 description 1
- 229960001265 ciclosporin Drugs 0.000 description 1
- 108010060348 citron-kinase Proteins 0.000 description 1
- 230000035602 clotting Effects 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 208000029742 colonic neoplasm Diseases 0.000 description 1
- 238000010835 comparative analysis Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940126543 compound 14 Drugs 0.000 description 1
- 229940125810 compound 20 Drugs 0.000 description 1
- 229940126086 compound 21 Drugs 0.000 description 1
- 229940126208 compound 22 Drugs 0.000 description 1
- 229940125833 compound 23 Drugs 0.000 description 1
- 229940125961 compound 24 Drugs 0.000 description 1
- 229940125846 compound 25 Drugs 0.000 description 1
- 229940125851 compound 27 Drugs 0.000 description 1
- 229940127204 compound 29 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125877 compound 31 Drugs 0.000 description 1
- 229940125878 compound 36 Drugs 0.000 description 1
- 229940125807 compound 37 Drugs 0.000 description 1
- 229940127573 compound 38 Drugs 0.000 description 1
- 229940126540 compound 41 Drugs 0.000 description 1
- 229940125936 compound 42 Drugs 0.000 description 1
- 229940125844 compound 46 Drugs 0.000 description 1
- 229940127271 compound 49 Drugs 0.000 description 1
- 229940126545 compound 53 Drugs 0.000 description 1
- 229940127113 compound 57 Drugs 0.000 description 1
- 229940125900 compound 59 Drugs 0.000 description 1
- 229940126179 compound 72 Drugs 0.000 description 1
- ONCCWDRMOZMNSM-FBCQKBJTSA-N compound Z Chemical compound N1=C2C(=O)NC(N)=NC2=NC=C1C(=O)[C@H]1OP(O)(=O)OC[C@H]1O ONCCWDRMOZMNSM-FBCQKBJTSA-N 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 229940038717 copaxone Drugs 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 239000012045 crude solution Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- SGJSQQLUMMGQOS-UHFFFAOYSA-N cyclohexanecarbonitrile Chemical compound N#C[C]1CCCCC1 SGJSQQLUMMGQOS-UHFFFAOYSA-N 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 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 1
- XDUCRNVZHNFBLF-UHFFFAOYSA-N cyclopenta-1,3-diene diphenylphosphane iron(2+) Chemical compound [CH-]1C=CC=C1.[CH-]1C=CC=C1.[Fe+2].C1(=CC=CC=C1)PC1=CC=CC=C1 XDUCRNVZHNFBLF-UHFFFAOYSA-N 0.000 description 1
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 229930182912 cyclosporin Natural products 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 1
- 229960003957 dexamethasone Drugs 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- GXGAKHNRMVGRPK-UHFFFAOYSA-N dimagnesium;dioxido-bis[[oxido(oxo)silyl]oxy]silane Chemical compound [Mg+2].[Mg+2].[O-][Si](=O)O[Si]([O-])([O-])O[Si]([O-])=O GXGAKHNRMVGRPK-UHFFFAOYSA-N 0.000 description 1
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 1
- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 1
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
- 229910000396 dipotassium phosphate Inorganic materials 0.000 description 1
- 235000019797 dipotassium phosphate Nutrition 0.000 description 1
- 208000037765 diseases and disorders Diseases 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- CETRZFQIITUQQL-UHFFFAOYSA-N dmso dimethylsulfoxide Chemical compound CS(C)=O.CS(C)=O CETRZFQIITUQQL-UHFFFAOYSA-N 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- 239000003221 ear drop Substances 0.000 description 1
- 229940047652 ear drops Drugs 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 239000012636 effector Substances 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000000132 electrospray ionisation Methods 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000008387 emulsifying waxe Substances 0.000 description 1
- 230000003511 endothelial effect Effects 0.000 description 1
- 239000007920 enema Substances 0.000 description 1
- 229940095399 enema Drugs 0.000 description 1
- BJXYHBKEQFQVES-NWDGAFQWSA-N enpatoran Chemical compound N[C@H]1CN(C[C@H](C1)C(F)(F)F)C1=C2C=CC=NC2=C(C=C1)C#N BJXYHBKEQFQVES-NWDGAFQWSA-N 0.000 description 1
- JRURYQJSLYLRLN-BJMVGYQFSA-N entacapone Chemical compound CCN(CC)C(=O)C(\C#N)=C\C1=CC(O)=C(O)C([N+]([O-])=O)=C1 JRURYQJSLYLRLN-BJMVGYQFSA-N 0.000 description 1
- 229960003337 entacapone Drugs 0.000 description 1
- 238000007824 enzymatic assay Methods 0.000 description 1
- 229940088598 enzyme Drugs 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- FPEUIONIYRKUDE-UHFFFAOYSA-N ethyl 2-(6-chloropyridin-2-yl)-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)C1=CC=CC(Cl)=N1 FPEUIONIYRKUDE-UHFFFAOYSA-N 0.000 description 1
- PBDURJZTWGJELL-UHFFFAOYSA-N ethyl 3-[1-(4-methylphenyl)sulfonylpyrrolo[2,3-b]pyridin-4-yl]benzoate Chemical compound CCOC(=O)C1=CC=CC(C=2C=3C=CN(C=3N=CC=2)S(=O)(=O)C=2C=CC(C)=CC=2)=C1 PBDURJZTWGJELL-UHFFFAOYSA-N 0.000 description 1
- GWNFQAKCJYEJEW-UHFFFAOYSA-N ethyl 3-[8-[[4-methyl-5-[(3-methyl-4-oxophthalazin-1-yl)methyl]-1,2,4-triazol-3-yl]sulfanyl]octanoylamino]benzoate Chemical compound CCOC(=O)C1=CC(NC(=O)CCCCCCCSC2=NN=C(CC3=NN(C)C(=O)C4=CC=CC=C34)N2C)=CC=C1 GWNFQAKCJYEJEW-UHFFFAOYSA-N 0.000 description 1
- VICYTAYPKBLQFB-UHFFFAOYSA-N ethyl 3-bromo-2-oxopropanoate Chemical compound CCOC(=O)C(=O)CBr VICYTAYPKBLQFB-UHFFFAOYSA-N 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003889 eye drop Substances 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
- 229960004979 fampridine Drugs 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 239000011152 fibreglass Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229960002949 fluorouracil Drugs 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 108010074605 gamma-Globulins Proteins 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- FVIZARNDLVOMSU-UHFFFAOYSA-N ginsenoside K Natural products C1CC(C2(CCC3C(C)(C)C(O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC1OC(CO)C(O)C(O)C1O FVIZARNDLVOMSU-UHFFFAOYSA-N 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 229940080856 gleevec Drugs 0.000 description 1
- 235000001727 glucose Nutrition 0.000 description 1
- YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
- SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 229960002449 glycine Drugs 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 239000003102 growth factor Substances 0.000 description 1
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000000262 haloalkenyl group Chemical group 0.000 description 1
- 229960003878 haloperidol Drugs 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000002489 hematologic effect Effects 0.000 description 1
- 230000002440 hepatic effect Effects 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 239000000017 hydrogel Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 1
- YLMAHDNUQAMNNX-UHFFFAOYSA-N imatinib methanesulfonate Chemical compound CS(O)(=O)=O.C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 YLMAHDNUQAMNNX-UHFFFAOYSA-N 0.000 description 1
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
- 208000026278 immune system disease Diseases 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 125000003453 indazolyl group Chemical class N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000007972 injectable composition Substances 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 229960001388 interferon-beta Drugs 0.000 description 1
- 230000031146 intracellular signal transduction Effects 0.000 description 1
- 238000007917 intracranial administration Methods 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000007919 intrasynovial administration Methods 0.000 description 1
- 238000007913 intrathecal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 239000000644 isotonic solution Substances 0.000 description 1
- 239000007951 isotonicity adjuster Substances 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 201000005992 juvenile myelomonocytic leukemia Diseases 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 229940001447 lactate Drugs 0.000 description 1
- 229940099584 lactobionate Drugs 0.000 description 1
- JYTUSYBCFIZPBE-AMTLMPIISA-N lactobionic acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O JYTUSYBCFIZPBE-AMTLMPIISA-N 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- RENRQMCACQEWFC-UGKGYDQZSA-N lnp023 Chemical compound C1([C@H]2N(CC=3C=4C=CNC=4C(C)=CC=3OC)CC[C@@H](C2)OCC)=CC=C(C(O)=O)C=C1 RENRQMCACQEWFC-UGKGYDQZSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 229910000386 magnesium trisilicate Inorganic materials 0.000 description 1
- 235000019793 magnesium trisilicate Nutrition 0.000 description 1
- 229940099273 magnesium trisilicate Drugs 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- RMIODHQZRUFFFF-UHFFFAOYSA-N methoxyacetic acid Chemical compound COCC(O)=O RMIODHQZRUFFFF-UHFFFAOYSA-N 0.000 description 1
- FZPYJVHTOBEPEL-UHFFFAOYSA-N methyl 4-(5-chloro-1h-pyrrolo[2,3-b]pyridin-4-yl)-1-(4-methylphenyl)sulfonylpyrrole-2-carboxylate Chemical compound COC(=O)C1=CC(C=2C=3C=CNC=3N=CC=2Cl)=CN1S(=O)(=O)C1=CC=C(C)C=C1 FZPYJVHTOBEPEL-UHFFFAOYSA-N 0.000 description 1
- VGSSBCZOBJXTGY-UHFFFAOYSA-N methyl 4-(5-fluoro-1h-pyrrolo[2,3-b]pyridin-4-yl)-1-(4-methylphenyl)sulfonylpyrrole-2-carboxylate Chemical compound COC(=O)C1=CC(C=2C=3C=CNC=3N=CC=2F)=CN1S(=O)(=O)C1=CC=C(C)C=C1 VGSSBCZOBJXTGY-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 229940042472 mineral oil Drugs 0.000 description 1
- KKZJGLLVHKMTCM-UHFFFAOYSA-N mitoxantrone Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO KKZJGLLVHKMTCM-UHFFFAOYSA-N 0.000 description 1
- 229960001156 mitoxantrone Drugs 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000002899 monoamine oxidase inhibitor Substances 0.000 description 1
- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 229960005127 montelukast Drugs 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- RTGDFNSFWBGLEC-SYZQJQIISA-N mycophenolate mofetil Chemical compound COC1=C(C)C=2COC(=O)C=2C(O)=C1C\C=C(/C)CCC(=O)OCCN1CCOCC1 RTGDFNSFWBGLEC-SYZQJQIISA-N 0.000 description 1
- ZNSGLAIHVWOISS-UHFFFAOYSA-N n,n-diethyl-6-(1h-pyrrolo[2,3-b]pyridin-4-yl)pyridin-2-amine Chemical compound CCN(CC)C1=CC=CC(C=2C=3C=CNC=3N=CC=2)=N1 ZNSGLAIHVWOISS-UHFFFAOYSA-N 0.000 description 1
- ZJYZNTBSMSFTQN-UHFFFAOYSA-N n,n-dimethyl-3-(1h-pyrrolo[2,3-b]pyridin-4-yl)aniline Chemical compound CN(C)C1=CC=CC(C=2C=3C=CNC=3N=CC=2)=C1 ZJYZNTBSMSFTQN-UHFFFAOYSA-N 0.000 description 1
- PDJXINMEZRMZHB-UHFFFAOYSA-N n,n-dimethyl-3-(1h-pyrrolo[2,3-b]pyridin-4-yl)benzamide Chemical compound CN(C)C(=O)C1=CC=CC(C=2C=3C=CNC=3N=CC=2)=C1 PDJXINMEZRMZHB-UHFFFAOYSA-N 0.000 description 1
- YZPKVQZHLPYRFN-UHFFFAOYSA-N n-(1,3-benzodioxol-5-ylmethyl)-6-(1h-pyrrolo[2,3-b]pyridin-4-yl)pyridin-2-amine Chemical compound C1=C2OCOC2=CC(CNC=2N=C(C=CC=2)C=2C=3C=CNC=3N=CC=2)=C1 YZPKVQZHLPYRFN-UHFFFAOYSA-N 0.000 description 1
- OACKTSUCFHTDGX-UHFFFAOYSA-N n-(2-methylbutyl)-6-(1h-pyrrolo[2,3-b]pyridin-4-yl)pyridin-2-amine Chemical compound CCC(C)CNC1=CC=CC(C=2C=3C=CNC=3N=CC=2)=N1 OACKTSUCFHTDGX-UHFFFAOYSA-N 0.000 description 1
- YQWXLQRHSDXQCM-UHFFFAOYSA-N n-(oxolan-2-ylmethyl)-6-(1h-pyrrolo[2,3-b]pyridin-4-yl)pyridin-2-amine Chemical compound C=1C=CC(C=2C=3C=CNC=3N=CC=2)=NC=1NCC1CCCO1 YQWXLQRHSDXQCM-UHFFFAOYSA-N 0.000 description 1
- VTKFRARPZADLQE-UHFFFAOYSA-N n-[(2-chlorophenyl)methyl]-6-(1h-pyrrolo[2,3-b]pyridin-4-yl)pyridin-2-amine Chemical compound ClC1=CC=CC=C1CNC1=CC=CC(C=2C=3C=CNC=3N=CC=2)=N1 VTKFRARPZADLQE-UHFFFAOYSA-N 0.000 description 1
- BVOVHHUEVHQTEZ-UHFFFAOYSA-N n-[(3-methoxyphenyl)methyl]-6-(1h-pyrrolo[2,3-b]pyridin-4-yl)pyridin-2-amine Chemical compound COC1=CC=CC(CNC=2N=C(C=CC=2)C=2C=3C=CNC=3N=CC=2)=C1 BVOVHHUEVHQTEZ-UHFFFAOYSA-N 0.000 description 1
- CGLSCMALYPFQLU-UHFFFAOYSA-N n-[2-(2-chlorophenyl)ethyl]-6-(1h-pyrrolo[2,3-b]pyridin-4-yl)pyridin-2-amine Chemical compound ClC1=CC=CC=C1CCNC1=CC=CC(C=2C=3C=CNC=3N=CC=2)=N1 CGLSCMALYPFQLU-UHFFFAOYSA-N 0.000 description 1
- ADPMJCQZIWIWAU-UHFFFAOYSA-N n-[2-(2-chlorophenyl)ethyl]-6-(5-chloro-1h-pyrrolo[2,3-b]pyridin-4-yl)pyridin-2-amine Chemical compound ClC1=CC=CC=C1CCNC1=CC=CC(C=2C=3C=CNC=3N=CC=2Cl)=N1 ADPMJCQZIWIWAU-UHFFFAOYSA-N 0.000 description 1
- QEUXBJNLUFUYRA-UHFFFAOYSA-N n-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=CC=NC2=C1C=CN2 QEUXBJNLUFUYRA-UHFFFAOYSA-N 0.000 description 1
- YGBMCLDVRUGXOV-UHFFFAOYSA-N n-[6-[6-chloro-5-[(4-fluorophenyl)sulfonylamino]pyridin-3-yl]-1,3-benzothiazol-2-yl]acetamide Chemical compound C1=C2SC(NC(=O)C)=NC2=CC=C1C(C=1)=CN=C(Cl)C=1NS(=O)(=O)C1=CC=C(F)C=C1 YGBMCLDVRUGXOV-UHFFFAOYSA-N 0.000 description 1
- XGYLUPDBTGIVMU-UHFFFAOYSA-N n-[[3-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methyl]cyclopropanamine Chemical compound C=1C=CC(C=2C=3C=CNC=3N=CC=2)=CC=1CNC1CC1 XGYLUPDBTGIVMU-UHFFFAOYSA-N 0.000 description 1
- SYWKJZVTOTXPDS-UHFFFAOYSA-N n-cyclopentyl-6-(1h-pyrrolo[2,3-b]pyridin-4-yl)pyridin-2-amine Chemical compound C1CCCC1NC1=CC=CC(C=2C=3C=CNC=3N=CC=2)=N1 SYWKJZVTOTXPDS-UHFFFAOYSA-N 0.000 description 1
- WOOWBQQQJXZGIE-UHFFFAOYSA-N n-ethyl-n-propan-2-ylpropan-2-amine Chemical compound CCN(C(C)C)C(C)C.CCN(C(C)C)C(C)C WOOWBQQQJXZGIE-UHFFFAOYSA-N 0.000 description 1
- OBKWWSIEURQEKL-UHFFFAOYSA-N n-methyl-1-[3-(1h-pyrrolo[2,3-b]pyridin-4-yl)phenyl]methanamine Chemical compound CNCC1=CC=CC(C=2C=3C=CNC=3N=CC=2)=C1 OBKWWSIEURQEKL-UHFFFAOYSA-N 0.000 description 1
- PPJKDMDFRWNPHA-UHFFFAOYSA-N n-methyl-n-(pyridin-3-ylmethyl)-6-(1h-pyrrolo[2,3-b]pyridin-4-yl)pyridin-2-amine Chemical compound C=1C=CC(C=2C=3C=CNC=3N=CC=2)=NC=1N(C)CC1=CC=CN=C1 PPJKDMDFRWNPHA-UHFFFAOYSA-N 0.000 description 1
- QRISDFBHHOWOLT-UHFFFAOYSA-N n-methyl-n-propan-2-yl-6-(1h-pyrrolo[2,3-b]pyridin-4-yl)pyridin-2-amine Chemical compound CC(C)N(C)C1=CC=CC(C=2C=3C=CNC=3N=CC=2)=N1 QRISDFBHHOWOLT-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-M naphthalene-2-sulfonate Chemical compound C1=CC=CC2=CC(S(=O)(=O)[O-])=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-M 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- VWBWQOUWDOULQN-UHFFFAOYSA-N nmp n-methylpyrrolidone Chemical compound CN1CCCC1=O.CN1CCCC1=O VWBWQOUWDOULQN-UHFFFAOYSA-N 0.000 description 1
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000002611 ovarian Effects 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229960001592 paclitaxel Drugs 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 201000002528 pancreatic cancer Diseases 0.000 description 1
- 208000008443 pancreatic carcinoma Diseases 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 229960004851 pergolide Drugs 0.000 description 1
- YEHCICAEULNIGD-MZMPZRCHSA-N pergolide Chemical compound C1=CC([C@H]2C[C@@H](CSC)CN([C@@H]2C2)CCC)=C3C2=CNC3=C1 YEHCICAEULNIGD-MZMPZRCHSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
- LWMPFIOTEAXAGV-UHFFFAOYSA-N piperidin-1-amine Chemical compound NN1CCCCC1 LWMPFIOTEAXAGV-UHFFFAOYSA-N 0.000 description 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
- 229950010765 pivalate Drugs 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 230000010118 platelet activation Effects 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920000747 poly(lactic acid) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004626 polylactic acid Substances 0.000 description 1
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 150000004804 polysaccharides Chemical class 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229940113124 polysorbate 60 Drugs 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000004302 potassium sorbate Substances 0.000 description 1
- 235000010241 potassium sorbate Nutrition 0.000 description 1
- 229940069338 potassium sorbate Drugs 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 229960003089 pramipexole Drugs 0.000 description 1
- FASDKYOPVNHBLU-ZETCQYMHSA-N pramipexole Chemical compound C1[C@@H](NCCC)CCC2=C1SC(N)=N2 FASDKYOPVNHBLU-ZETCQYMHSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- NSETWVJZUWGCKE-UHFFFAOYSA-N propylphosphonic acid Chemical compound CCCP(O)(O)=O NSETWVJZUWGCKE-UHFFFAOYSA-N 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- ICSNLGPSRYBMBD-CDYZYAPPSA-N pyridin-2-amine Chemical class NC1=CC=CC=[15N]1 ICSNLGPSRYBMBD-CDYZYAPPSA-N 0.000 description 1
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 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
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 230000001698 pyrogenic effect Effects 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- ZTHJULTYCAQOIJ-WXXKFALUSA-N quetiapine fumarate Chemical compound [H+].[H+].[O-]C(=O)\C=C\C([O-])=O.C1CN(CCOCCO)CCN1C1=NC2=CC=CC=C2SC2=CC=CC=C12.C1CN(CCOCCO)CCN1C1=NC2=CC=CC=C2SC2=CC=CC=C12 ZTHJULTYCAQOIJ-WXXKFALUSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- ZAHRKKWIAAJSAO-UHFFFAOYSA-N rapamycin Natural products COCC(O)C(=C/C(C)C(=O)CC(OC(=O)C1CCCCN1C(=O)C(=O)C2(O)OC(CC(OC)C(=CC=CC=CC(C)CC(C)C(=O)C)C)CCC2C)C(C)CC3CCC(O)C(C3)OC)C ZAHRKKWIAAJSAO-UHFFFAOYSA-N 0.000 description 1
- 229940038850 rebif Drugs 0.000 description 1
- 238000011084 recovery Methods 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
- 239000003340 retarding agent Substances 0.000 description 1
- 102000007268 rho GTP-Binding Proteins Human genes 0.000 description 1
- 108010033674 rho GTP-Binding Proteins Proteins 0.000 description 1
- 229960004181 riluzole Drugs 0.000 description 1
- 229940106887 risperdal Drugs 0.000 description 1
- RAPZEAPATHNIPO-UHFFFAOYSA-N risperidone Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCCC4=NC=3C)=NOC2=C1 RAPZEAPATHNIPO-UHFFFAOYSA-N 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 229960002052 salbutamol Drugs 0.000 description 1
- 210000003296 saliva Anatomy 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 229940035004 seroquel Drugs 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- QFJCIRLUMZQUOT-HPLJOQBZSA-N sirolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 description 1
- 229960002930 sirolimus Drugs 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 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
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- NCEXYHBECQHGNR-QZQOTICOSA-N sulfasalazine Chemical compound C1=C(O)C(C(=O)O)=CC(\N=N\C=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-QZQOTICOSA-N 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
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 229960001967 tacrolimus Drugs 0.000 description 1
- QJJXYPPXXYFBGM-SHYZHZOCSA-N tacrolimus Natural products CO[C@H]1C[C@H](CC[C@@H]1O)C=C(C)[C@H]2OC(=O)[C@H]3CCCCN3C(=O)C(=O)[C@@]4(O)O[C@@H]([C@H](C[C@H]4C)OC)[C@@H](C[C@H](C)CC(=C[C@@H](CC=C)C(=O)C[C@H](O)[C@H]2C)C)OC QJJXYPPXXYFBGM-SHYZHZOCSA-N 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 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
- QNGTVGAIEOIQBR-UHFFFAOYSA-N tert-butyl n-(4-bromothiophen-2-yl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(Br)=CS1 QNGTVGAIEOIQBR-UHFFFAOYSA-N 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 210000001685 thyroid gland Anatomy 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 229960000303 topotecan Drugs 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 230000009959 type I hypersensitivity Effects 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical class CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
- 229960004528 vincristine Drugs 0.000 description 1
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000003871 white petrolatum Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4745—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- 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
- A61P15/06—Antiabortive agents; Labour repressants
-
- 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
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
-
- 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
-
- 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
- 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
- A61P25/14—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
- A61P25/28—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
- 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
- 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
- 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
- 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
- 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
- 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
- A61P9/10—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
-
- 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
- A61P9/12—Antihypertensives
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Rheumatology (AREA)
- Oncology (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Endocrinology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Heart & Thoracic Surgery (AREA)
- Virology (AREA)
- Gynecology & Obstetrics (AREA)
- Psychiatry (AREA)
- Reproductive Health (AREA)
- Hematology (AREA)
- Psychology (AREA)
- Dermatology (AREA)
- Communicable Diseases (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- Urology & Nephrology (AREA)
- Ophthalmology & Optometry (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US68355405P | 2005-05-20 | 2005-05-20 | |
| US683554P | 2005-05-20 | ||
| PCT/US2006/019711 WO2006127587A1 (en) | 2005-05-20 | 2006-05-22 | Pyrrolopyridines useful as inhibitors of protein kinase |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2380795T3 true ES2380795T3 (es) | 2012-05-18 |
Family
ID=36940144
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES06770824T Active ES2380795T3 (es) | 2005-05-20 | 2006-05-22 | Pirrolopiridinas útiles como inhibidores de proteínas quinasas |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US8921376B2 (enExample) |
| EP (3) | EP2354139A1 (enExample) |
| JP (3) | JP2008545660A (enExample) |
| KR (1) | KR20080016659A (enExample) |
| CN (1) | CN101228161B (enExample) |
| AT (1) | ATE540948T1 (enExample) |
| AU (1) | AU2006251623A1 (enExample) |
| CA (1) | CA2609126A1 (enExample) |
| ES (1) | ES2380795T3 (enExample) |
| IL (1) | IL187438A0 (enExample) |
| MX (1) | MX2007014619A (enExample) |
| NO (1) | NO20076502L (enExample) |
| NZ (1) | NZ564065A (enExample) |
| RU (2) | RU2435769C2 (enExample) |
| WO (1) | WO2006127587A1 (enExample) |
| ZA (1) | ZA200710379B (enExample) |
Families Citing this family (174)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1925855B (zh) | 2003-12-19 | 2010-06-16 | 普莱希科公司 | 开发Ret调节剂的化合物和方法 |
| CA2560454C (en) | 2004-03-30 | 2013-05-21 | Vertex Pharmaceuticals Incorporated | Azaindoles useful as inhibitors of jak and other protein kinases |
| US7498342B2 (en) | 2004-06-17 | 2009-03-03 | Plexxikon, Inc. | Compounds modulating c-kit activity |
| MX2007014377A (es) | 2005-05-17 | 2008-02-06 | Plexxikon Inc | Inhibidores de proteina cinasa de derivados de pirrol (2,3-b) piridina. |
| ES2380795T3 (es) * | 2005-05-20 | 2012-05-18 | Vertex Pharmaceuticals, Inc. | Pirrolopiridinas útiles como inhibidores de proteínas quinasas |
| DK2395004T3 (en) | 2005-06-22 | 2016-03-21 | Plexxikon Inc | Pyrrolo [2,3-b] pyridine derivatives as protein kinase inhibitors |
| CA2615291A1 (en) | 2005-07-14 | 2007-01-18 | Astellas Pharma Inc. | Heterocyclic janus kinase 3 inhibitors |
| CN102127078A (zh) | 2005-07-14 | 2011-07-20 | 安斯泰来制药株式会社 | Janus激酶3的杂环类抑制剂 |
| EP2270014A1 (en) | 2005-09-22 | 2011-01-05 | Incyte Corporation | Azepine inhibitors of janus kinases |
| AU2015201850B2 (en) * | 2005-12-13 | 2017-03-02 | Incyte Holdings Corporation | Heteroaryl substituted pyrrolo[2,3-b]pyridines and pyrrolo[2,3-b]pyrimidines as Janus kinase inhibitors |
| DK3184526T3 (en) | 2005-12-13 | 2019-01-14 | Incyte Holdings Corp | PYRROLO [2,3-D] PYRIMIDINE DERIVATIVES AS A JANUS-KINASE INHIBITOR |
| EP1968568A4 (en) * | 2005-12-22 | 2011-04-13 | Glaxosmithkline Llc | HEMMER OF NUTS ACTIVITY |
| EP2537849A3 (en) | 2006-01-17 | 2013-04-03 | Vertex Pharmaceuticals, Inc. | Azaindoles useful as inhibitors of janus kinases |
| KR101081293B1 (ko) * | 2006-01-18 | 2011-11-08 | 에프. 호프만-라 로슈 아게 | 11 베타-에이치에스디1 억제제로서 티아졸 |
| EP1979353A2 (en) * | 2006-01-19 | 2008-10-15 | OSI Pharmaceuticals, Inc. | Fused heterobicyclic kinase inhibitors |
| RU2008143361A (ru) * | 2006-04-05 | 2010-05-10 | Вертекс Фармасьютикалз Инкорпорейтед (Us) | Деазапурины в качестве ингибиторов янус-киназ |
| WO2007136790A2 (en) * | 2006-05-18 | 2007-11-29 | Mannkind Corporation | Intracellular kinase inhibitors |
| US8063050B2 (en) * | 2006-07-06 | 2011-11-22 | Array Biopharma Inc. | Hydroxylated and methoxylated pyrimidyl cyclopentanes as AKT protein kinase inhibitors |
| DK2049500T3 (da) * | 2006-07-06 | 2011-12-12 | Array Biopharma Inc | Cyclopenta [d]-pyrimidiner som AKT-proteinkinase-inhibitorer |
| SI2054418T1 (sl) | 2006-07-06 | 2012-02-29 | Array Biopharma Inc | Dihidrotieno pirimidini kot AKT protein kinazni inhibitorji |
| WO2008006025A1 (en) | 2006-07-06 | 2008-01-10 | Array Biopharma Inc. | Dihydrofuro pyrimidines as akt protein kinase inhibitors |
| CN101600714B (zh) * | 2006-11-10 | 2013-08-21 | 百时美施贵宝公司 | 吡咯并吡啶激酶抑制剂 |
| WO2008063888A2 (en) | 2006-11-22 | 2008-05-29 | Plexxikon, Inc. | Compounds modulating c-fms and/or c-kit activity and uses therefor |
| US8071779B2 (en) * | 2006-12-18 | 2011-12-06 | Inspire Pharmaceuticals, Inc. | Cytoskeletal active rho kinase inhibitor compounds, composition and use |
| NZ577798A (en) | 2006-12-21 | 2012-04-27 | Vertex Pharma | 5-cyano-4- (pyrrolo [2, 3b] pyridine-3-yl) -pyrimidine derivatives useful as protein kinase inhibitors |
| PE20081581A1 (es) | 2006-12-21 | 2008-11-12 | Plexxikon Inc | COMPUESTOS PIRROLO[2,3-b]PIRIDINAS COMO MODULADORES DE QUINASA |
| US7872018B2 (en) | 2006-12-21 | 2011-01-18 | Plexxikon, Inc. | Compounds and methods for kinase modulation, and indications therefor |
| WO2008079909A1 (en) | 2006-12-21 | 2008-07-03 | Plexxikon, Inc. | Pyrrolo [2,3-b] pyridines as kinase modulators |
| US8513270B2 (en) | 2006-12-22 | 2013-08-20 | Incyte Corporation | Substituted heterocycles as Janus kinase inhibitors |
| EP2123651A4 (en) | 2007-01-12 | 2011-05-04 | Astellas Pharma Inc | CONDENSED PYRIDINE COMPOUND |
| AU2008228768A1 (en) * | 2007-03-22 | 2008-09-25 | Vertex Pharmaceuticals Incorporated | N-heterocyclic compounds useful as inhibitors of Janus Kinases |
| CA2687931C (en) | 2007-05-31 | 2016-05-24 | Boehringer Ingelheim International Gmbh | Ccr2 receptor antagonists and uses thereof |
| GB0710528D0 (en) * | 2007-06-01 | 2007-07-11 | Glaxo Group Ltd | Novel compounds |
| CL2008001709A1 (es) | 2007-06-13 | 2008-11-03 | Incyte Corp | Compuestos derivados de pirrolo [2,3-b]pirimidina, moduladores de quinasas jak; composicion farmaceutica; y uso en el tratamiento de enfermedades tales como cancer, psoriasis, artritis reumatoide, entre otras. |
| EP2740731B1 (en) | 2007-06-13 | 2016-03-23 | Incyte Holdings Corporation | Crystalline salts of the janus kinase inhibitor (r)-3-(4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h-pyrazol-1-yl)-3-cyclopentylpropanenitrile |
| KR20150091196A (ko) * | 2007-07-05 | 2015-08-07 | 어레이 바이오파마 인크. | Ａｋｔ 단백질 키나제 억제제로서의 피리미딜 시클로펜탄 |
| CN101801955B (zh) | 2007-07-05 | 2013-05-08 | 阵列生物制药公司 | 作为akt蛋白激酶抑制剂的嘧啶基环戊烷 |
| US8846683B2 (en) | 2007-07-05 | 2014-09-30 | Array Biopharma, Inc. | Pyrimidyl cyclopentanes as Akt protein kinase inhibitors |
| US9409886B2 (en) | 2007-07-05 | 2016-08-09 | Array Biopharma Inc. | Pyrimidyl cyclopentanes as AKT protein kinase inhibitors |
| EP2170830B1 (en) | 2007-07-17 | 2014-10-15 | Plexxikon, Inc. | 2-FLUORO-BENZENESULFONAMIDE COMPOUNDS AS Raf KINASE MODULATORS |
| WO2009089352A1 (en) | 2008-01-08 | 2009-07-16 | Array Biopharma Inc. | Pyrrolopyridines as kinase inhibitors |
| CA2711699A1 (en) * | 2008-01-09 | 2009-07-16 | Array Biopharma Inc. | Hydroxylated pyrimidyl cyclopentanes as akt protein kinase inhibitors |
| JP5608098B2 (ja) * | 2008-01-09 | 2014-10-15 | アレイ バイオファーマ、インコーポレイテッド | キナーゼ阻害薬としてのピラゾロピリジン |
| KR101624752B1 (ko) * | 2008-01-09 | 2016-05-26 | 어레이 바이오파마 인크. | Ａｋｔ 단백질 키나제 저해물질로써의 수산화된 피리미딜 시클로펜탄 |
| GB0801416D0 (en) * | 2008-01-25 | 2008-03-05 | Piramed Ltd | Pharmaceutical compounds |
| WO2009145814A2 (en) * | 2008-03-10 | 2009-12-03 | Vertex Pharmaceuticals Incorporated | Pyrimidines and pyridines useful as inhibitors of protein kinases |
| ES2602577T3 (es) | 2008-03-11 | 2017-02-21 | Incyte Holdings Corporation | Derivados de azetidina y ciclobutano como inhibidores de JAK |
| GB0804592D0 (en) * | 2008-03-12 | 2008-04-16 | Glaxo Group Ltd | Novel compounds |
| AR071717A1 (es) * | 2008-05-13 | 2010-07-07 | Array Biopharma Inc | Pirrolo[2,3-b]piridinas inhibidoras de quinasas chk1 y chk2,composiciones farmaceuticas que las contienen,proceso para prepararlas y uso de las mismas en el tratamiento y prevencion del cancer. |
| US8822513B2 (en) | 2010-03-01 | 2014-09-02 | Gtx, Inc. | Compounds for treatment of cancer |
| DK2959900T3 (en) * | 2008-06-16 | 2017-06-26 | Univ Tennessee Res Found | CONNECTION TO TREATMENT OF CANCER |
| US9447049B2 (en) | 2010-03-01 | 2016-09-20 | University Of Tennessee Research Foundation | Compounds for treatment of cancer |
| US9029408B2 (en) | 2008-06-16 | 2015-05-12 | Gtx, Inc. | Compounds for treatment of cancer |
| CL2009001884A1 (es) * | 2008-10-02 | 2010-05-14 | Incyte Holdings Corp | Uso de 3-ciclopentil-3-[4-(7h-pirrolo[2,3-d]pirimidin-4-il)-1h-pirazol-1-il)propanonitrilo, inhibidor de janus quinasa, y uso de una composición que lo comprende para el tratamiento del ojo seco. |
| DE102008052943A1 (de) | 2008-10-23 | 2010-04-29 | Merck Patent Gmbh | Azaindolderivate |
| CN103724328B (zh) | 2008-12-19 | 2015-10-14 | 贝林格尔.英格海姆国际有限公司 | 作为ccr2受体拮抗剂用于治疗炎症、哮喘和copd的环状嘧啶-4-甲酰胺 |
| KR20170058465A (ko) | 2009-04-03 | 2017-05-26 | 에프. 호프만-라 로슈 아게 | 프로판-１-술폰산 ｛３-［５-（４-클로로-페닐）-１Ｈ-피롤로［２，３-ｂ］피리딘-３-카르보닐］-２，４-디플루오로-페닐｝-아미드 조성물 및 그의 용도 |
| WO2010135621A1 (en) * | 2009-05-22 | 2010-11-25 | Incyte Corporation | 3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h-pyrazol-1-yl]octane- or heptane-nitrile as jak inhibitors |
| ES2487542T3 (es) * | 2009-05-22 | 2014-08-21 | Incyte Corporation | Derivados de N-(hetero)aril-pirrolidina de pirazol-4-il-pirrolo[2,3-d]pirimidinas y pirrol-3-il-pirrolo[2,3-d]pirimidinas como inhibidores de cinasas Janus |
| GEP20207129B (en) | 2009-06-17 | 2020-07-10 | Vertex Pharma | Inhibitors of influenza viruses replication |
| TW201105674A (en) | 2009-07-08 | 2011-02-16 | Leo Pharma As | Novel JAK receptor and protein tyrosine kinase inhibitors and pharmaceutical use thereof |
| TWI466885B (zh) * | 2009-07-31 | 2015-01-01 | Japan Tobacco Inc | 含氮螺環化合物及其醫藥用途 |
| US8329724B2 (en) | 2009-08-03 | 2012-12-11 | Hoffmann-La Roche Inc. | Process for the manufacture of pharmaceutically active compounds |
| US8569295B2 (en) * | 2009-08-06 | 2013-10-29 | Merck Patent Gmbh | Bicyclic urea compounds |
| SG178273A1 (en) * | 2009-08-07 | 2012-03-29 | Merck Patent Gmbh | Novel azaheterocyclic compounds |
| NZ597983A (en) | 2009-08-20 | 2014-05-30 | Karus Therapeutics Ltd | Tricyclic heterocyclic compounds as phosphoinositide 3-kinase inhibitors |
| WO2011028685A1 (en) | 2009-09-01 | 2011-03-10 | Incyte Corporation | Heterocyclic derivatives of pyrazol-4-yl-pyrrolo[2,3-d]pyrimidines as janus kinase inhibitors |
| RU2538204C2 (ru) | 2009-09-10 | 2015-01-10 | Ф.Хоффманн-Ля Рош Аг | Ингибиторы jak |
| CA2777114C (en) | 2009-10-09 | 2018-10-23 | Incyte Corporation | Hydroxyl, keto, and glucuronide derivatives of 3-(4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h-pyrazol-1-yl)-3-cyclopentylpropanenitrile |
| AU2010315126B2 (en) | 2009-11-06 | 2015-06-25 | Plexxikon, Inc. | Compounds and methods for kinase modulation, and indications therefor |
| PL2513093T3 (pl) | 2009-12-17 | 2015-03-31 | Centrexion Therapeutics Corp | Nowi antagoniści receptora CCR2 i ich zastosowanie |
| USRE49251E1 (en) | 2010-01-04 | 2022-10-18 | Mapi Pharma Ltd. | Depot systems comprising glatiramer or pharmacologically acceptable salt thereof |
| AU2011217961B2 (en) * | 2010-02-18 | 2016-05-05 | Incyte Holdings Corporation | Cyclobutane and methylcyclobutane derivatives as Janus kinase inhibitors |
| CN102883607B (zh) | 2010-03-01 | 2015-07-22 | Gtx公司 | 用于治疗癌的化合物 |
| SMT201800137T1 (it) | 2010-03-10 | 2018-07-17 | Incyte Holdings Corp | Derivati di piperidin-4-il azetidina come inibitori di jak1 |
| JP2013526507A (ja) | 2010-05-12 | 2013-06-24 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 新規ｃｃｒ２受容体アンタゴニスト、その製造方法及び薬物としてのその使用 |
| EP2569295B1 (en) | 2010-05-12 | 2014-11-19 | Boehringer Ingelheim International GmbH | New ccr2 receptor antagonists, method for producing the same, and use thereof as medicaments |
| US8841313B2 (en) | 2010-05-17 | 2014-09-23 | Boehringer Ingelheim International Gmbh | CCR2 antagonists and uses thereof |
| PH12012502296B1 (en) | 2010-05-21 | 2017-10-06 | Incyte Holdings Corp | Topical formulation for a jak inhibitor |
| JP5636094B2 (ja) | 2010-05-25 | 2014-12-03 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｃｃｒ２受容体アンタゴニスト |
| EP2576538B1 (en) | 2010-06-01 | 2015-10-28 | Boehringer Ingelheim International GmbH | New CCR2 antagonists |
| EP2397482A1 (en) * | 2010-06-15 | 2011-12-21 | Almirall, S.A. | Heteroaryl imidazolone derivatives as jak inhibitors |
| ES2536415T3 (es) | 2010-11-19 | 2015-05-25 | Incyte Corporation | Pirrolopiridinas y pirrolopirimidinas sustituidas heterocíclicas como inhibidores de JAK |
| SG190839A1 (en) | 2010-11-19 | 2013-07-31 | Incyte Corp | Cyclobutyl substituted pyrrolopyridine and pyrrolopyrimidine derivatives as jak inhibitors |
| CN103492381A (zh) | 2010-12-16 | 2014-01-01 | 沃泰克斯药物股份有限公司 | 流感病毒复制的抑制剂 |
| BR112013017184A2 (pt) | 2011-01-07 | 2016-09-20 | Leo Pharma As | composto, composição farmacêutica, uso de um composto, e, método para evitar, tratar ou melhorar doenças |
| WO2012109075A1 (en) | 2011-02-07 | 2012-08-16 | Plexxikon Inc. | Compounds and methods for kinase modulation, and indications therefor |
| ES2547916T3 (es) | 2011-02-18 | 2015-10-09 | Novartis Pharma Ag | Terapia de combinación de inhibidores de mTOR/JAK |
| TWI558702B (zh) | 2011-02-21 | 2016-11-21 | 普雷辛肯公司 | 醫藥活性物質的固態形式 |
| CN103841976A (zh) | 2011-04-01 | 2014-06-04 | 基因泰克公司 | Akt和mek抑制剂化合物的组合及其使用方法 |
| WO2012135759A1 (en) | 2011-04-01 | 2012-10-04 | Genentech, Inc. | Combinations of akt inhibitor compounds and abiraterone, and methods of use |
| WO2012177606A1 (en) | 2011-06-20 | 2012-12-27 | Incyte Corporation | Azetidinyl phenyl, pyridyl or pyrazinyl carboxamide derivatives as jak inhibitors |
| EP2729465A2 (en) | 2011-07-05 | 2014-05-14 | Vertex Pharmaceuticals Incorporated | Processes and intermediates for producing azaindoles |
| WO2013010839A1 (en) | 2011-07-15 | 2013-01-24 | Boehringer Ingelheim International Gmbh | Novel and selective ccr2 antagonists |
| UA118010C2 (uk) | 2011-08-01 | 2018-11-12 | Вертекс Фармасьютікалз Інкорпорейтед | Інгібітори реплікації вірусів грипу |
| JP2014521725A (ja) | 2011-08-10 | 2014-08-28 | ノバルティス・ファルマ・アクチェンゲゼルシャフト | ＪＡＫＰＩ３Ｋ／ｍＴＯＲ併用療法 |
| TW201313721A (zh) | 2011-08-18 | 2013-04-01 | Incyte Corp | 作為ｊａｋ抑制劑之環己基氮雜環丁烷衍生物 |
| UA111854C2 (uk) | 2011-09-07 | 2016-06-24 | Інсайт Холдінгс Корпорейшн | Способи і проміжні сполуки для отримання інгібіторів jak |
| GB201204125D0 (en) * | 2012-03-08 | 2012-04-25 | Karus Therapeutics Ltd | Compounds |
| WO2013148748A1 (en) * | 2012-03-29 | 2013-10-03 | Francis Xavier Tavares | Lactam kinase inhibitors |
| WO2013173720A1 (en) | 2012-05-18 | 2013-11-21 | Incyte Corporation | Piperidinylcyclobutyl substituted pyrrolopyridine and pyrrolopyrimidine derivatives as jak inhibitors |
| US9150570B2 (en) | 2012-05-31 | 2015-10-06 | Plexxikon Inc. | Synthesis of heterocyclic compounds |
| WO2014013014A1 (en) | 2012-07-18 | 2014-01-23 | Fundació Privada Centre De Regulació Genòmica (Crg) | Jak inhibitors for activation of epidermal stem cell populations |
| EP2917202B1 (en) | 2012-11-07 | 2018-05-02 | Karus Therapeutics Limited | Novel histone deacetylase inhibitors and their use in therapy |
| PE20151157A1 (es) | 2012-11-15 | 2015-08-19 | Incyte Corp | Formas de dosificacion de ruxolitinib de liberacion sostenida |
| FR3001219A1 (fr) * | 2013-01-22 | 2014-07-25 | Centre Nat Rech Scient | Inhibiteurs de kinases |
| WO2014138212A1 (en) * | 2013-03-06 | 2014-09-12 | Allosteros Therapeutics, Inc. | CaMKII INHIBITORS AND USES THEREOF |
| LT3489239T (lt) | 2013-03-06 | 2022-03-10 | Incyte Holdings Corporation | Jak inhibitoriaus gamybos būdai ir tarpiniai junginiai |
| US20140271460A1 (en) | 2013-03-15 | 2014-09-18 | G1 Therapeutics, Inc. | Highly Active Anti-Neoplastic and Anti-Proliferative Agents |
| CN105473140B (zh) | 2013-03-15 | 2018-04-10 | G1治疗公司 | 在化学疗法期间对正常细胞的瞬时保护 |
| JP6118453B2 (ja) * | 2013-04-02 | 2017-04-19 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | ブルトンチロシンキナーゼの阻害剤 |
| KR101790090B1 (ko) * | 2013-05-02 | 2017-10-25 | 후지필름 가부시키가이샤 | 에칭 방법, 이에 이용하는 에칭액 및 에칭액의 키트, 및 반도체 기판 제품의 제조 방법 |
| CN105358550B (zh) | 2013-05-10 | 2018-04-06 | 卡鲁斯治疗有限公司 | 组蛋白脱乙酰基酶抑制剂 |
| UA120499C2 (uk) | 2013-08-07 | 2019-12-26 | Інсайт Корпорейшн | Лікування захворювань із застосуванням лікарських форм з уповільненим вивільненням для інгібітора jak1 |
| HRP20191525T1 (hr) | 2013-11-13 | 2019-11-29 | Vertex Pharma | Inhibitori replikacije virusa influence |
| EP3421468B1 (en) | 2013-11-13 | 2020-11-04 | Vertex Pharmaceuticals Incorporated | Methods of preparing inhibitors of influenza viruses replication |
| TR201820925T4 (tr) * | 2014-02-04 | 2019-01-21 | Taiho Pharmaceutical Co Ltd | Azaindol türevi. |
| GB201402431D0 (en) | 2014-02-12 | 2014-03-26 | Karus Therapeutics Ltd | Compounds |
| EP2924026A1 (en) | 2014-03-28 | 2015-09-30 | Novartis Tiergesundheit AG | Aminosulfonylmethylcyclohexanes as JAK inhibitors |
| WO2015161285A1 (en) | 2014-04-17 | 2015-10-22 | G1 Therapeutics, Inc. | Tricyclic lactams for use in the protection of hematopoietic stem and progenitor cells against ionizing radiation |
| AU2015265696B2 (en) * | 2014-05-28 | 2018-01-18 | Astrazeneca Ab | Processes for the preparation of AZD5363 and novel intermediate used therein |
| WO2015184305A1 (en) | 2014-05-30 | 2015-12-03 | Incyte Corporation | TREATMENT OF CHRONIC NEUTROPHILIC LEUKEMIA (CNL) AND ATYPICAL CHRONIC MYELOID LEUKEMIA (aCML) BY INHIBITORS OF JAK1 |
| JP6633618B2 (ja) * | 2014-08-21 | 2020-01-22 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | 強力なｒｏｃｋ阻害剤としてのタイドバックのベンズアミド誘導体 |
| CN107074856A (zh) | 2014-09-05 | 2017-08-18 | 阿略斯泰罗斯医疗公司 | CaMKII抑制剂及其用途 |
| WO2016040848A1 (en) | 2014-09-12 | 2016-03-17 | G1 Therapeutics, Inc. | Treatment of rb-negative tumors using topoisomerase inhibitors in combination with cyclin dependent kinase 4/6 inhibitors |
| EP3191098A4 (en) | 2014-09-12 | 2018-04-25 | G1 Therapeutics, Inc. | Combinations and dosing regimes to treat rb-positive tumors |
| GB201419228D0 (en) | 2014-10-29 | 2014-12-10 | Karus Therapeutics Ltd | Compounds |
| GB201419264D0 (en) | 2014-10-29 | 2014-12-10 | Karus Therapeutics Ltd | Compounds |
| CN105837572B (zh) * | 2015-02-02 | 2019-04-19 | 四川大学 | N-取代苯基酰胺衍生物及其制备方法和用途 |
| JP6704416B2 (ja) | 2015-05-13 | 2020-06-03 | 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Ｖｅｒｔｅｘ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃｏｒｐｏｒａｔｅｄ | インフルエンザウイルスの複製の阻害剤を調製する方法 |
| WO2016183120A1 (en) | 2015-05-13 | 2016-11-17 | Vertex Pharmaceuticals Incorporated | Inhibitors of influenza viruses replication |
| AU2016287584B2 (en) | 2015-07-02 | 2020-03-26 | Centrexion Therapeutics Corporation | (4-((3R,4R)-3-methoxytetrahydro-pyran-4-ylamino)piperidin-1-yl)(5-methyl-6-(((2R,6S)-6-(p-tolyl)tetrahydro-2H-pyran-2-yl)methylamino)pyrimidin-4yl)methanone citrate |
| GB201514751D0 (en) | 2015-08-19 | 2015-09-30 | Karus Therapeutics Ltd | Compounds |
| GB201514760D0 (en) | 2015-08-19 | 2015-09-30 | Karus Therapeutics Ltd | Compounds and method of use |
| GB201514754D0 (en) | 2015-08-19 | 2015-09-30 | Karus Therapeutics Ltd | Compounds |
| GB201514758D0 (en) | 2015-08-19 | 2015-09-30 | Karus Therapeutics Ltd | Formulation |
| HK1250707B (zh) | 2015-12-11 | 2020-07-03 | 四川科伦博泰生物医药股份有限公司 | 氮杂环丁烷衍生物、其制备方法及用途 |
| CN106928252B (zh) * | 2015-12-31 | 2019-09-27 | 成都先导药物开发股份有限公司 | 一种抑制rock的化合物及其制备方法与应用 |
| EP3492468B1 (en) | 2016-07-26 | 2022-02-23 | Suzhou Longbiotech Pharmaceuticals Co., Ltd. | Heterocyclic compound as jak inhibitor, and salts and therapeutic use thereof |
| US12097292B2 (en) | 2016-08-28 | 2024-09-24 | Mapi Pharma Ltd. | Process for preparing microparticles containing glatiramer acetate |
| JP7193448B2 (ja) | 2016-08-31 | 2022-12-20 | マピ ファーマ リミテッド | 酢酸グラチラマーを含むデポシステム |
| WO2018041989A1 (en) | 2016-09-02 | 2018-03-08 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for diagnosing and treating refractory celiac disease type 2 |
| AU2018239798B2 (en) | 2017-03-23 | 2020-08-27 | Daegu Gyeongbuk Institute Of Science And Technology | Pyrrolo-pyridine derivative compound, method for preparing same, and pharmaceutical composition containing same as active ingredient for prevention or treatment of protein kinase-related diseases |
| CN110382052A (zh) | 2017-03-26 | 2019-10-25 | Mapi医药公司 | 用于治疗进展型形式的多发性硬化症的格拉替雷储库系统 |
| 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 |
| CA3063616A1 (en) | 2017-06-30 | 2019-12-06 | Beijing Tide Pharmaceutical Co., Ltd. | Rho-associated protein kinase inhibitor, pharmaceutical composition comprising same, and preparation method and use thereof |
| CN110573501B (zh) | 2017-06-30 | 2023-09-29 | 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 |
| CA3072861A1 (en) * | 2017-08-23 | 2019-02-28 | Sprint Bioscience Ab | Azaindolylpyridone and diazaindolylpyridone compounds |
| CN109535164B (zh) * | 2017-09-21 | 2022-01-18 | 上海华汇拓医药科技有限公司 | Jak激酶抑制剂及其制备方法和在医药领域的应用 |
| US10800775B2 (en) * | 2017-11-03 | 2020-10-13 | Aclaris Therapeutics, Inc. | Pyrazolyl pyrrolo[2,3-b]pyrmidine-5-carboxylate analogs and methods of making the same |
| SG11202002947TA (en) | 2017-11-03 | 2020-04-29 | Aclaris Therapeutics Inc | Substituted pyrrolopyrimidine jak inhibitors and methods of making and using the same |
| WO2019113487A1 (en) | 2017-12-08 | 2019-06-13 | Incyte Corporation | Low dose combination therapy for treatment of myeloproliferative neoplasms |
| IL276302B2 (en) | 2018-01-30 | 2023-11-01 | Incyte Corp | Procedures for preparing [1-(3-fluoro-2-(trifluoromethyl(isonicotinyl}piperidine-4-one) |
| CN112771025B (zh) * | 2018-03-23 | 2024-02-27 | 重庆复创医药研究有限公司 | 作为rock抑制剂的氘代化合物 |
| SMT202400306T1 (it) | 2018-03-30 | 2024-09-16 | Incyte Corp | Trattamento dell'idrosadenite suppurativa utilizzando inibitori di jak. |
| BR112021002479A2 (pt) | 2018-08-10 | 2021-07-27 | Aclaris Therapeutics, Inc. | composto, composição farmacêutica, método para inibir a atividade de itk ou jak3 em uma população de células, método para tratar um distúrbio mediado por itk ou jak3 em um indivíduo necessitando do mesmo e uso de um composto |
| US12275731B2 (en) | 2018-10-16 | 2025-04-15 | Dana-Farber Cancer Institute, Inc. | Azaindole inhibitors of wild-type and mutant forms of LRRK2 |
| CA3168211A1 (en) | 2019-01-18 | 2020-07-23 | Voronoi Co., Ltd. | Pyrrolopyridine derivative and use thereof for preventing or treating protein kinase related disease |
| EP3947737A2 (en) | 2019-04-02 | 2022-02-09 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods of predicting and preventing cancer in patients having premalignant lesions |
| WO2020212395A1 (en) | 2019-04-16 | 2020-10-22 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Use of jak inhibitors for the treatment of painful conditions involving nav1.7 channels |
| CN113727975A (zh) * | 2019-05-02 | 2021-11-30 | 阿克拉瑞斯治疗股份有限公司 | 作为jak抑制剂的被取代的吡咯并吡啶 |
| CA3143636A1 (en) * | 2019-07-12 | 2021-01-21 | Michael Lim | Compositions and methods for treating cerebral vasospasm |
| US20220372135A1 (en) | 2019-09-27 | 2022-11-24 | Disc Medicine, Inc. | Methods for treating myelofibrosis and related conditions |
| CR20220280A (es) | 2019-11-22 | 2022-09-02 | Incyte Corp | Terapia de combinación que comprende un inhibidor de alk2 y un inhibidor de jak2 |
| IL297437A (en) | 2020-05-13 | 2022-12-01 | Disc Medicine Inc | Anti-hemojuvelin (hjv) antibodies for treating myelofibrosis |
| EP3915990A1 (en) * | 2020-05-26 | 2021-12-01 | Centre National de la Recherche Scientifique | 4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-3,6-dihydropyridine-1-(2h)-carboxamide derivatives as limk and/or rock kinases inhibitors for use in the treatment of cancer |
| US11833155B2 (en) | 2020-06-03 | 2023-12-05 | Incyte Corporation | Combination therapy for treatment of myeloproliferative neoplasms |
| US10988479B1 (en) | 2020-06-15 | 2021-04-27 | G1 Therapeutics, Inc. | Morphic forms of trilaciclib and methods of manufacture thereof |
| KR20220081631A (ko) | 2020-12-09 | 2022-06-16 | 보로노이 주식회사 | 염증성 질환의 예방 및/또는 치료를 위한 피롤로-피리딘 유도체 화합물의 신규 용도 |
| CN113402523B (zh) * | 2021-07-13 | 2022-07-12 | 西安交通大学 | 一种靶向肥大细胞MrgX2小分子荧光探针及制备方法和应用 |
| CN113735859A (zh) * | 2021-08-12 | 2021-12-03 | 安徽医科大学 | 一种激酶抑制剂 |
| EP4471004A1 (en) | 2022-01-28 | 2024-12-04 | Nippon Soda Co., Ltd. | Method for producing amide compound |
| CN117050075A (zh) * | 2022-05-05 | 2023-11-14 | 中国药科大学 | 一类联芳环类bet抑制剂及合成方法与用途 |
| US20250283174A1 (en) | 2022-05-16 | 2025-09-11 | Institut National de la Santé et de la Recherche Médicale | Methods for assessing the exhaustion of hematopoietic stem cells induced by chronic inflammation |
Family Cites Families (56)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5304121A (en) | 1990-12-28 | 1994-04-19 | Boston Scientific Corporation | Drug delivery system making use of a hydrogel polymer coating |
| US5994341A (en) | 1993-07-19 | 1999-11-30 | Angiogenesis Technologies, Inc. | Anti-angiogenic Compositions and methods for the treatment of arthritis |
| US6099562A (en) | 1996-06-13 | 2000-08-08 | Schneider (Usa) Inc. | Drug coating with topcoat |
| PE20010306A1 (es) * | 1999-07-02 | 2001-03-29 | Agouron Pharma | Compuestos de indazol y composiciones farmaceuticas que los contienen utiles para la inhibicion de proteina kinasa |
| WO2001047922A2 (en) | 1999-12-24 | 2001-07-05 | Aventis Pharma Limited | Azaindoles |
| AU4878601A (en) * | 2000-04-20 | 2001-11-07 | Mitsubishi Corporation | Aromatic amide compounds |
| US6335342B1 (en) * | 2000-06-19 | 2002-01-01 | Pharmacia & Upjohn S.P.A. | Azaindole derivatives, process for their preparation, and their use as antitumor agents |
| HU230302B1 (hu) | 2000-10-20 | 2015-12-28 | Eisai R&D Management Co., Ltd. | Nitrogéntartalmú aromás származékok és ezeket tartalmazó gyógyászati készítmények |
| GB0115109D0 (en) * | 2001-06-21 | 2001-08-15 | Aventis Pharma Ltd | Chemical compounds |
| GB0202679D0 (en) | 2002-02-05 | 2002-03-20 | Glaxo Group Ltd | Novel compounds |
| US7304061B2 (en) * | 2002-04-26 | 2007-12-04 | Vertex Pharmaceuticals Incorporated | Heterocyclic inhibitors of ERK2 and uses thereof |
| DE50304983D1 (de) | 2002-10-28 | 2006-10-19 | Bayer Healthcare Ag | Heteroaryloxy-substituierte phenylaminopyrimidine als rho-kinaseinhibitoren |
| GB0227240D0 (en) * | 2002-11-21 | 2002-12-31 | Glaxo Group Ltd | Compounds |
| AU2003297160A1 (en) * | 2002-12-18 | 2004-07-22 | Vertex Pharmaceuticals Incorporated | Benzisoxazole derivatives useful as inhibitors of protein kinases |
| WO2004072063A1 (en) * | 2003-02-07 | 2004-08-26 | Vertex Pharmaceuticals Incorporated | Heteroaryl substituted pyrolls useful as inhibitors of protein kinases |
| CN100482662C (zh) * | 2003-02-14 | 2009-04-29 | 惠氏公司 | 作为5-羟基色胺-6配体的杂环基-3-磺酰基氮杂吲哚或-氮杂吲唑衍生物 |
| US7531553B2 (en) * | 2003-03-21 | 2009-05-12 | Amgen Inc. | Heterocyclic compounds and methods of use |
| SE0301372D0 (sv) | 2003-05-09 | 2003-05-09 | Astrazeneca Ab | Novel compounds |
| FR2857661B1 (fr) * | 2003-07-15 | 2006-09-22 | Snc Eurokera | Produit en vitroceramique avec joint(s) de soudure; fabrication |
| US20050043346A1 (en) | 2003-08-08 | 2005-02-24 | Pharmacia Italia S.P.A. | Pyridylpyrrole derivatives active as kinase inhibitors |
| AR045595A1 (es) * | 2003-09-04 | 2005-11-02 | Vertex Pharma | Composiciones utiles como inhibidores de proteinas quinasas |
| FR2861729B1 (fr) * | 2003-10-31 | 2006-09-08 | Fabre Pierre Dermo Cosmetique | Monomere d'alkyl-rhamnose ou d'alkyl-fucose, medicament comprenant un monomere d'alkyl-sucre reducteur |
| FR2862363B1 (fr) * | 2003-11-18 | 2007-01-26 | Antonov Automotive Europ | Dispositif de transmission a rapports multiples, notamment pour l'automobile |
| AU2004293026B2 (en) * | 2003-11-21 | 2012-01-19 | Array Biopharma Inc. | AKT protein kinase inhibitors |
| CN1925855B (zh) | 2003-12-19 | 2010-06-16 | 普莱希科公司 | 开发Ret调节剂的化合物和方法 |
| FR2868273B1 (fr) * | 2004-03-30 | 2006-07-07 | Parfums Christian Dior Sa | Presentoir d'articles tels que des produits cosmetiques |
| CA2560454C (en) * | 2004-03-30 | 2013-05-21 | Vertex Pharmaceuticals Incorporated | Azaindoles useful as inhibitors of jak and other protein kinases |
| EP1756108A2 (en) * | 2004-04-02 | 2007-02-28 | Vertex Pharmaceuticals Incorporated | Azaindoles useful as inhibitors of rock and other protein kinases |
| DE102004020570A1 (de) * | 2004-04-27 | 2005-11-24 | Bayer Healthcare Ag | Substituierte Phenylaminopyrimidine |
| ES2505090T3 (es) * | 2004-05-07 | 2014-10-09 | Amgen Inc. | Derivados heterocíclicos nitrogenados como moduladores de proteína cinasas y su uso para el tratamiento de angiogénesis y cáncer |
| US20060122213A1 (en) * | 2004-06-30 | 2006-06-08 | Francoise Pierard | Azaindoles useful as inhibitors of protein kinases |
| WO2006017443A2 (en) | 2004-08-02 | 2006-02-16 | Osi Pharmaceuticals, Inc. | Aryl-amino substituted pyrrolopyrimidine multi-kinase inhibiting compounds |
| US7605168B2 (en) * | 2004-09-03 | 2009-10-20 | Plexxikon, Inc. | PDE4B inhibitors |
| FR2874920B1 (fr) * | 2004-09-09 | 2006-10-20 | Sanofi Aventis Sa | Derives de 3-spiro-indolin-2-one comme ligand des recepteurs de la vasopressine |
| NZ553646A (en) | 2004-09-22 | 2010-07-30 | Janssen Pharmaceutica Nv | Inhibitors of the interaction between MDM2 and p53 |
| ATE479687T1 (de) * | 2004-10-15 | 2010-09-15 | Takeda Pharmaceutical | Kinaseinhibitoren |
| MY179032A (en) * | 2004-10-25 | 2020-10-26 | Cancer Research Tech Ltd | Ortho-condensed pyridine and pyrimidine derivatives (e.g.purines) as protein kinase inhibitors |
| UY29177A1 (es) * | 2004-10-25 | 2006-05-31 | Astex Therapeutics Ltd | Derivados sustituidos de purina, purinona y deazapurina, composiciones que los contienen métodos para su preparación y sus usos |
| US7528138B2 (en) * | 2004-11-04 | 2009-05-05 | Vertex Pharmaceuticals Incorporated | Pyrazolo[1,5-a]pyrimidines useful as inhibitors of protein kinases |
| WO2006052568A2 (en) | 2004-11-10 | 2006-05-18 | Eli Lilly And Company | Tgf-beta inhibitors |
| US20060122185A1 (en) * | 2004-11-22 | 2006-06-08 | Jeremy Green | Bicyclic inhibitors of Rho kinase |
| AR054416A1 (es) * | 2004-12-22 | 2007-06-27 | Incyte Corp | Pirrolo [2,3-b]piridin-4-il-aminas y pirrolo [2,3-b]pirimidin-4-il-aminas como inhibidores de las quinasas janus. composiciones farmaceuticas. |
| CA2590261C (en) * | 2004-12-27 | 2011-08-16 | Alcon, Inc. | Aminopyrazine analogs for treating glaucoma and other rho kinase-mediated diseases and conditions |
| GB0501999D0 (en) * | 2005-02-01 | 2005-03-09 | Sentinel Oncology Ltd | Pharmaceutical compounds |
| ES2320487T3 (es) * | 2005-02-03 | 2009-05-22 | Vertex Pharmaceuticals, Inc. | Pirrolopirimidinas utiles como inhibidores de proteina quinasas. |
| BRPI0610828A2 (pt) * | 2005-05-16 | 2010-07-27 | Irm Llc | compostos e composições como inibidores de proteìna quinase |
| ES2380795T3 (es) | 2005-05-20 | 2012-05-18 | Vertex Pharmaceuticals, Inc. | Pirrolopiridinas útiles como inhibidores de proteínas quinasas |
| ES2401192T3 (es) * | 2005-09-30 | 2013-04-17 | Vertex Pharmceuticals Incorporated | Deazapurinas útiles como inhibidores de janus cinasas |
| EP2537849A3 (en) * | 2006-01-17 | 2013-04-03 | Vertex Pharmaceuticals, Inc. | Azaindoles useful as inhibitors of janus kinases |
| EP1979353A2 (en) * | 2006-01-19 | 2008-10-15 | OSI Pharmaceuticals, Inc. | Fused heterobicyclic kinase inhibitors |
| RU2008143361A (ru) | 2006-04-05 | 2010-05-10 | Вертекс Фармасьютикалз Инкорпорейтед (Us) | Деазапурины в качестве ингибиторов янус-киназ |
| NZ577798A (en) * | 2006-12-21 | 2012-04-27 | Vertex Pharma | 5-cyano-4- (pyrrolo [2, 3b] pyridine-3-yl) -pyrimidine derivatives useful as protein kinase inhibitors |
| JP2009123635A (ja) * | 2007-11-19 | 2009-06-04 | Nissan Diesel Motor Co Ltd | ハーネス組立体 |
| GEP20207129B (en) * | 2009-06-17 | 2020-07-10 | Vertex Pharma | Inhibitors of influenza viruses replication |
| WO2012083122A1 (en) * | 2010-12-16 | 2012-06-21 | Vertex Pharmaceutical Incorporated | Inhibitors of influenza viruses replication |
| UA118010C2 (uk) * | 2011-08-01 | 2018-11-12 | Вертекс Фармасьютікалз Інкорпорейтед | Інгібітори реплікації вірусів грипу |
-
2006
- 2006-05-22 ES ES06770824T patent/ES2380795T3/es active Active
- 2006-05-22 RU RU2007147455/04A patent/RU2435769C2/ru not_active IP Right Cessation
- 2006-05-22 CA CA002609126A patent/CA2609126A1/en not_active Abandoned
- 2006-05-22 AT AT06770824T patent/ATE540948T1/de active
- 2006-05-22 WO PCT/US2006/019711 patent/WO2006127587A1/en not_active Ceased
- 2006-05-22 NZ NZ564065A patent/NZ564065A/en not_active IP Right Cessation
- 2006-05-22 KR KR1020077029764A patent/KR20080016659A/ko not_active Ceased
- 2006-05-22 EP EP10188694A patent/EP2354139A1/en not_active Withdrawn
- 2006-05-22 MX MX2007014619A patent/MX2007014619A/es not_active Application Discontinuation
- 2006-05-22 ZA ZA200710379A patent/ZA200710379B/xx unknown
- 2006-05-22 CN CN2006800263918A patent/CN101228161B/zh not_active Expired - Fee Related
- 2006-05-22 JP JP2008512591A patent/JP2008545660A/ja active Pending
- 2006-05-22 EP EP10188700A patent/EP2354140A1/en not_active Withdrawn
- 2006-05-22 AU AU2006251623A patent/AU2006251623A1/en not_active Abandoned
- 2006-05-22 EP EP06770824A patent/EP1881983B1/en not_active Not-in-force
- 2006-05-22 US US11/438,748 patent/US8921376B2/en not_active Expired - Fee Related
-
2007
- 2007-11-18 IL IL187438A patent/IL187438A0/en unknown
- 2007-12-18 NO NO20076502A patent/NO20076502L/no not_active Application Discontinuation
-
2009
- 2009-05-21 JP JP2009123635A patent/JP2009179644A/ja active Pending
-
2011
- 2011-08-11 RU RU2011133825/04A patent/RU2011133825A/ru not_active Application Discontinuation
-
2013
- 2013-09-24 JP JP2013196681A patent/JP2013253114A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| WO2006127587A1 (en) | 2006-11-30 |
| JP2009179644A (ja) | 2009-08-13 |
| ATE540948T1 (de) | 2012-01-15 |
| US8921376B2 (en) | 2014-12-30 |
| CN101228161A (zh) | 2008-07-23 |
| RU2435769C2 (ru) | 2011-12-10 |
| ZA200710379B (en) | 2009-05-27 |
| NO20076502L (no) | 2008-02-19 |
| RU2007147455A (ru) | 2009-06-27 |
| RU2011133825A (ru) | 2013-02-20 |
| IL187438A0 (en) | 2008-02-09 |
| US20070135466A1 (en) | 2007-06-14 |
| AU2006251623A1 (en) | 2006-11-30 |
| CN101228161B (zh) | 2012-10-10 |
| NZ564065A (en) | 2011-03-31 |
| EP1881983B1 (en) | 2012-01-11 |
| JP2008545660A (ja) | 2008-12-18 |
| CA2609126A1 (en) | 2006-11-30 |
| KR20080016659A (ko) | 2008-02-21 |
| EP2354140A1 (en) | 2011-08-10 |
| EP2354139A1 (en) | 2011-08-10 |
| JP2013253114A (ja) | 2013-12-19 |
| MX2007014619A (es) | 2009-02-13 |
| EP1881983A1 (en) | 2008-01-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES2380795T3 (es) | Pirrolopiridinas útiles como inhibidores de proteínas quinasas | |
| ES2320487T3 (es) | Pirrolopirimidinas utiles como inhibidores de proteina quinasas. | |
| JP5144532B2 (ja) | ｃ−Ｍｅｔ阻害剤及び用法 | |
| AU2018210196B2 (en) | Pyridine compounds as allosteric SHP2 inhibitors | |
| JP5469666B2 (ja) | ｃＭＥＴ阻害剤 | |
| ES2401192T3 (es) | Deazapurinas útiles como inhibidores de janus cinasas | |
| NL1029016C2 (nl) | Tetrahydronafthyridinederivaten. | |
| ES2882432T3 (es) | Amidas de 5 miembros y heterocíclicas bicíclicas como inhibidores de ROCK | |
| ES2544289T3 (es) | Derivados de quinolina y quinoxalina como inhibidores de cinasa | |
| ES2770693T3 (es) | Derivados de imidazopiridazina como inhibidores de caseína quinasa 1 delta/épsilon | |
| JP2010514676A (ja) | タンパク質キナーゼ阻害剤として有用な５−シアノ−４−（ピロロ［２，３ｂ］ピリジン−３−イル）−ピリミジン誘導体 | |
| JP2009532475A (ja) | ヤヌスキナーゼの阻害剤として有用なデアザプリン | |
| JP2008520745A (ja) | Ｒｈｏキナーゼの二環式阻害剤 | |
| JP2008528705A5 (enExample) | ||
| HK1054034A1 (en) | Substituted pyrrolopyridinone derivatives useful as phosphodiesterase inhibitors | |
| WO2019189555A1 (ja) | 複素環化合物 | |
| CN116437918A (zh) | 作为tam抑制剂的吡唑并吡啶化合物 | |
| HK1122794A (en) | Pyrrolopyridines useful as inhibitors of protein kinase | |
| HK1125106A (en) | Inhibitors of c-met and uses thereof |