BRPI0618179A2 - inibidores de biaril meta pirimidina de cinases - Google Patents
inibidores de biaril meta pirimidina de cinases Download PDFInfo
- Publication number
- BRPI0618179A2 BRPI0618179A2 BRPI0618179-1A BRPI0618179A BRPI0618179A2 BR PI0618179 A2 BRPI0618179 A2 BR PI0618179A2 BR PI0618179 A BRPI0618179 A BR PI0618179A BR PI0618179 A2 BRPI0618179 A2 BR PI0618179A2
- Authority
- BR
- Brazil
- Prior art keywords
- formula
- original document
- see original
- document page
- compound
- Prior art date
Links
- 229940043355 kinase inhibitor Drugs 0.000 title claims description 6
- 125000005841 biaryl group Chemical group 0.000 title abstract 2
- 239000003757 phosphotransferase inhibitor Substances 0.000 title description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title 1
- 108091000080 Phosphotransferase Proteins 0.000 claims abstract description 15
- 102000020233 phosphotransferase Human genes 0.000 claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims description 476
- -1 aryl carbon Chemical compound 0.000 claims description 118
- 238000006243 chemical reaction Methods 0.000 claims description 104
- 229920002472 Starch Chemical group 0.000 claims description 65
- 235000019698 starch Nutrition 0.000 claims description 65
- 239000008107 starch Chemical group 0.000 claims description 65
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 61
- 238000000034 method Methods 0.000 claims description 61
- 208000035475 disorder Diseases 0.000 claims description 41
- 125000003118 aryl group Chemical group 0.000 claims description 35
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 31
- 239000008194 pharmaceutical composition Substances 0.000 claims description 30
- 150000003839 salts Chemical group 0.000 claims description 27
- 229910052799 carbon Inorganic materials 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 125000001072 heteroaryl group Chemical group 0.000 claims description 21
- 206010028980 Neoplasm Diseases 0.000 claims description 20
- 102000042838 JAK family Human genes 0.000 claims description 19
- 108091082332 JAK family Proteins 0.000 claims description 19
- 201000010099 disease Diseases 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 125000005842 heteroatom Chemical group 0.000 claims description 18
- 238000011282 treatment Methods 0.000 claims description 18
- 239000003795 chemical substances by application Substances 0.000 claims description 17
- 125000000623 heterocyclic group Chemical group 0.000 claims description 17
- 150000004677 hydrates Chemical group 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 239000012453 solvate Chemical group 0.000 claims description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 150000001204 N-oxides Chemical class 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 208000014767 Myeloproliferative disease Diseases 0.000 claims description 13
- 201000011510 cancer Diseases 0.000 claims description 13
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 11
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 11
- 239000002246 antineoplastic agent Substances 0.000 claims description 10
- 230000035772 mutation Effects 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 230000001225 therapeutic effect Effects 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 239000005022 packaging material Substances 0.000 claims description 9
- 206010012689 Diabetic retinopathy Diseases 0.000 claims description 8
- 208000006673 asthma Diseases 0.000 claims description 8
- 229940127089 cytotoxic agent Drugs 0.000 claims description 8
- 201000007914 proliferative diabetic retinopathy Diseases 0.000 claims description 8
- 108090000623 proteins and genes Proteins 0.000 claims description 8
- 206010021143 Hypoxia Diseases 0.000 claims description 7
- 230000002491 angiogenic effect Effects 0.000 claims description 7
- 230000007954 hypoxia Effects 0.000 claims description 7
- 210000000056 organ Anatomy 0.000 claims description 7
- 208000032027 Essential Thrombocythemia Diseases 0.000 claims description 6
- 206010020751 Hypersensitivity Diseases 0.000 claims description 6
- 201000004681 Psoriasis Diseases 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims description 5
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 5
- 206010061218 Inflammation Diseases 0.000 claims description 5
- 206010039710 Scleroderma Diseases 0.000 claims description 5
- 239000011230 binding agent Substances 0.000 claims description 5
- 206010012601 diabetes mellitus Diseases 0.000 claims description 5
- 208000030533 eye disease Diseases 0.000 claims description 5
- 230000004054 inflammatory process Effects 0.000 claims description 5
- 208000032839 leukemia Diseases 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 5
- 208000037244 polycythemia vera Diseases 0.000 claims description 5
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 5
- 206010005003 Bladder cancer Diseases 0.000 claims description 4
- 206010005949 Bone cancer Diseases 0.000 claims description 4
- 208000018084 Bone neoplasm Diseases 0.000 claims description 4
- 208000003174 Brain Neoplasms Diseases 0.000 claims description 4
- 206010006187 Breast cancer Diseases 0.000 claims description 4
- 208000026310 Breast neoplasm Diseases 0.000 claims description 4
- 206010009944 Colon cancer Diseases 0.000 claims description 4
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 4
- 208000008839 Kidney Neoplasms Diseases 0.000 claims description 4
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 4
- 206010025323 Lymphomas Diseases 0.000 claims description 4
- 208000002231 Muscle Neoplasms Diseases 0.000 claims description 4
- 206010033128 Ovarian cancer Diseases 0.000 claims description 4
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 4
- 206010060862 Prostate cancer Diseases 0.000 claims description 4
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 4
- 206010038389 Renal cancer Diseases 0.000 claims description 4
- 208000000453 Skin Neoplasms Diseases 0.000 claims description 4
- 208000006011 Stroke Diseases 0.000 claims description 4
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 4
- 208000036142 Viral infection Diseases 0.000 claims description 4
- 241000700605 Viruses Species 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 201000008937 atopic dermatitis Diseases 0.000 claims description 4
- 208000029742 colonic neoplasm Diseases 0.000 claims description 4
- 208000014951 hematologic disease Diseases 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 201000010982 kidney cancer Diseases 0.000 claims description 4
- 201000007270 liver cancer Diseases 0.000 claims description 4
- 208000014018 liver neoplasm Diseases 0.000 claims description 4
- 201000005202 lung cancer Diseases 0.000 claims description 4
- 208000020816 lung neoplasm Diseases 0.000 claims description 4
- 201000006417 multiple sclerosis Diseases 0.000 claims description 4
- 201000002077 muscle cancer Diseases 0.000 claims description 4
- 230000004770 neurodegeneration Effects 0.000 claims description 4
- 201000000849 skin cancer Diseases 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 201000005112 urinary bladder cancer Diseases 0.000 claims description 4
- 230000009385 viral infection Effects 0.000 claims description 4
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims description 3
- 208000024827 Alzheimer disease Diseases 0.000 claims description 3
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 3
- 201000001320 Atherosclerosis Diseases 0.000 claims description 3
- 208000023275 Autoimmune disease Diseases 0.000 claims description 3
- 208000019838 Blood disease Diseases 0.000 claims description 3
- 206010007572 Cardiac hypertrophy Diseases 0.000 claims description 3
- 208000006029 Cardiomegaly Diseases 0.000 claims description 3
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims description 3
- 208000011231 Crohn disease Diseases 0.000 claims description 3
- 206010012442 Dermatitis contact Diseases 0.000 claims description 3
- 208000004262 Food Hypersensitivity Diseases 0.000 claims description 3
- 206010016946 Food allergy Diseases 0.000 claims description 3
- 208000005176 Hepatitis C Diseases 0.000 claims description 3
- 208000007514 Herpes zoster Diseases 0.000 claims description 3
- 241000701044 Human gammaherpesvirus 4 Species 0.000 claims description 3
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 3
- 208000026072 Motor neurone disease Diseases 0.000 claims description 3
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims description 3
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 3
- 208000021386 Sjogren Syndrome Diseases 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 201000009961 allergic asthma Diseases 0.000 claims description 3
- 208000002029 allergic contact dermatitis Diseases 0.000 claims description 3
- 201000010105 allergic rhinitis Diseases 0.000 claims description 3
- 230000007815 allergy Effects 0.000 claims description 3
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 3
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 3
- 230000001363 autoimmune Effects 0.000 claims description 3
- 201000001155 extrinsic allergic alveolitis Diseases 0.000 claims description 3
- 235000020932 food allergy Nutrition 0.000 claims description 3
- 208000018706 hematopoietic system disease Diseases 0.000 claims description 3
- 208000002672 hepatitis B Diseases 0.000 claims description 3
- 208000022098 hypersensitivity pneumonitis Diseases 0.000 claims description 3
- 230000002519 immonomodulatory effect Effects 0.000 claims description 3
- 208000027866 inflammatory disease Diseases 0.000 claims description 3
- 208000005264 motor neuron disease Diseases 0.000 claims description 3
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 3
- 208000005987 polymyositis Diseases 0.000 claims description 3
- 239000003909 protein kinase inhibitor Substances 0.000 claims description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims description 2
- 206010055128 Autoimmune neutropenia Diseases 0.000 claims description 2
- 201000006474 Brain Ischemia Diseases 0.000 claims description 2
- 206010008120 Cerebral ischaemia Diseases 0.000 claims description 2
- 206010008909 Chronic Hepatitis Diseases 0.000 claims description 2
- 208000000668 Chronic Pancreatitis Diseases 0.000 claims description 2
- 101100295738 Gallus gallus COR3 gene Proteins 0.000 claims description 2
- 206010018364 Glomerulonephritis Diseases 0.000 claims description 2
- 208000003807 Graves Disease Diseases 0.000 claims description 2
- 208000015023 Graves' disease Diseases 0.000 claims description 2
- 206010019755 Hepatitis chronic active Diseases 0.000 claims description 2
- 208000023105 Huntington disease Diseases 0.000 claims description 2
- 101100533890 Hypocrea jecorina (strain QM6a) sor3 gene Proteins 0.000 claims description 2
- 101100533874 Hypocrea jecorina (strain QM6a) sor5 gene Proteins 0.000 claims description 2
- 208000034578 Multiple myelomas Diseases 0.000 claims description 2
- 206010029113 Neovascularisation Diseases 0.000 claims description 2
- 206010029350 Neurotoxicity Diseases 0.000 claims description 2
- 206010033645 Pancreatitis Diseases 0.000 claims description 2
- 206010033647 Pancreatitis acute Diseases 0.000 claims description 2
- 206010033649 Pancreatitis chronic Diseases 0.000 claims description 2
- 208000018737 Parkinson disease Diseases 0.000 claims description 2
- 206010035226 Plasma cell myeloma Diseases 0.000 claims description 2
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims description 2
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims description 2
- 206010063897 Renal ischaemia Diseases 0.000 claims description 2
- 208000024799 Thyroid disease Diseases 0.000 claims description 2
- 206010044221 Toxic encephalopathy Diseases 0.000 claims description 2
- 206010052779 Transplant rejections Diseases 0.000 claims description 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 2
- 201000003229 acute pancreatitis Diseases 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 2
- 230000033115 angiogenesis Effects 0.000 claims description 2
- 201000005000 autoimmune gastritis Diseases 0.000 claims description 2
- 206010008118 cerebral infarction Diseases 0.000 claims description 2
- 206010009887 colitis Diseases 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 206010020718 hyperplasia Diseases 0.000 claims description 2
- 208000014674 injury Diseases 0.000 claims description 2
- 208000037906 ischaemic injury Diseases 0.000 claims description 2
- 206010025135 lupus erythematosus Diseases 0.000 claims description 2
- 206010028417 myasthenia gravis Diseases 0.000 claims description 2
- 208000010125 myocardial infarction Diseases 0.000 claims description 2
- 208000031225 myocardial ischemia Diseases 0.000 claims description 2
- 230000007135 neurotoxicity Effects 0.000 claims description 2
- 231100000228 neurotoxicity Toxicity 0.000 claims description 2
- 230000010410 reperfusion Effects 0.000 claims description 2
- 206010039083 rhinitis Diseases 0.000 claims description 2
- 208000010110 spontaneous platelet aggregation Diseases 0.000 claims description 2
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical group [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 2
- 229940124530 sulfonamide Drugs 0.000 claims description 2
- 150000003456 sulfonamides Chemical group 0.000 claims description 2
- 206010043554 thrombocytopenia Diseases 0.000 claims description 2
- 230000008736 traumatic injury Effects 0.000 claims description 2
- 230000002792 vascular Effects 0.000 claims description 2
- 201000007224 Myeloproliferative neoplasm Diseases 0.000 claims 9
- 239000013078 crystal Chemical group 0.000 claims 9
- 206010016654 Fibrosis Diseases 0.000 claims 5
- 206010028561 Myeloid metaplasia Diseases 0.000 claims 4
- 208000017733 acquired polycythemia vera Diseases 0.000 claims 4
- 239000003937 drug carrier Substances 0.000 claims 4
- 230000004761 fibrosis Effects 0.000 claims 4
- 230000002496 gastric effect Effects 0.000 claims 3
- 229910006074 SO2NH2 Inorganic materials 0.000 claims 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
- 230000012743 protein tagging Effects 0.000 claims 2
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 1
- 206010008190 Cerebrovascular accident Diseases 0.000 claims 1
- 208000009329 Graft vs Host Disease Diseases 0.000 claims 1
- 208000007766 Kaposi sarcoma Diseases 0.000 claims 1
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 1
- 208000017442 Retinal disease Diseases 0.000 claims 1
- 206010038923 Retinopathy Diseases 0.000 claims 1
- 206010043781 Thyroiditis chronic Diseases 0.000 claims 1
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims 1
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 1
- 208000007502 anemia Diseases 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- 208000001969 capillary hemangioma Diseases 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 208000026106 cerebrovascular disease Diseases 0.000 claims 1
- 230000007882 cirrhosis Effects 0.000 claims 1
- 208000019425 cirrhosis of liver Diseases 0.000 claims 1
- 239000003889 eye drop Substances 0.000 claims 1
- 229940012356 eye drops Drugs 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- 208000024908 graft versus host disease Diseases 0.000 claims 1
- 230000002949 hemolytic effect Effects 0.000 claims 1
- 230000000366 juvenile effect Effects 0.000 claims 1
- 210000001165 lymph node Anatomy 0.000 claims 1
- 208000003154 papilloma Diseases 0.000 claims 1
- 230000002062 proliferating effect Effects 0.000 claims 1
- 125000003748 selenium group Chemical group *[Se]* 0.000 claims 1
- 230000001629 suppression Effects 0.000 claims 1
- 238000011200 topical administration Methods 0.000 claims 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
- 102000005962 receptors Human genes 0.000 abstract description 4
- 108020003175 receptors Proteins 0.000 abstract description 4
- 102000001253 Protein Kinase Human genes 0.000 abstract description 3
- 108060006633 protein kinase Proteins 0.000 abstract description 3
- 108091005682 Receptor kinases Proteins 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 150000003230 pyrimidines Chemical class 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 351
- 239000000203 mixture Substances 0.000 description 337
- 239000007787 solid Substances 0.000 description 315
- 239000000543 intermediate Substances 0.000 description 250
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 245
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 240
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 189
- 239000000706 filtrate Substances 0.000 description 181
- 235000019439 ethyl acetate Nutrition 0.000 description 169
- 239000000243 solution Substances 0.000 description 169
- CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 160
- 238000005160 1H NMR spectroscopy Methods 0.000 description 133
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 132
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 126
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 112
- 238000004128 high performance liquid chromatography Methods 0.000 description 111
- 239000012044 organic layer Substances 0.000 description 107
- 239000012267 brine Substances 0.000 description 104
- 229910000024 caesium carbonate Inorganic materials 0.000 description 104
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 104
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 87
- 239000011734 sodium Substances 0.000 description 80
- 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 67
- 238000001816 cooling Methods 0.000 description 66
- 229960000583 acetic acid Drugs 0.000 description 63
- 238000001914 filtration Methods 0.000 description 62
- 239000000872 buffer Substances 0.000 description 61
- 238000010992 reflux Methods 0.000 description 61
- 239000010410 layer Substances 0.000 description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 51
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 47
- 239000002904 solvent Substances 0.000 description 45
- 239000000725 suspension Substances 0.000 description 44
- 239000012300 argon atmosphere Substances 0.000 description 43
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 37
- ZCQWIJBRCXQUNP-UHFFFAOYSA-N 2-chloro-5-methylpyrimidin-4-amine Chemical compound CC1=CN=C(Cl)N=C1N ZCQWIJBRCXQUNP-UHFFFAOYSA-N 0.000 description 35
- 239000012043 crude product Substances 0.000 description 35
- 239000011541 reaction mixture Substances 0.000 description 35
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 33
- 229920006395 saturated elastomer Polymers 0.000 description 29
- 239000000741 silica gel Substances 0.000 description 26
- 229910002027 silica gel Inorganic materials 0.000 description 26
- 238000000746 purification Methods 0.000 description 25
- 230000002829 reductive effect Effects 0.000 description 25
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 22
- 150000003840 hydrochlorides Chemical class 0.000 description 21
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 19
- 238000010898 silica gel chromatography Methods 0.000 description 18
- 239000003112 inhibitor Substances 0.000 description 17
- OTYZNDKWNPQQJP-UHFFFAOYSA-N 4-(2-pyrrolidin-1-ylethoxy)aniline Chemical compound C1=CC(N)=CC=C1OCCN1CCCC1 OTYZNDKWNPQQJP-UHFFFAOYSA-N 0.000 description 16
- 238000003818 flash chromatography Methods 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 14
- 238000005481 NMR spectroscopy Methods 0.000 description 13
- 239000003814 drug Substances 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 239000000546 pharmaceutical excipient Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 229910052786 argon Inorganic materials 0.000 description 11
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 11
- 241001660687 Xantho Species 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 239000004480 active ingredient Substances 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
- 239000002243 precursor Substances 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 230000014759 maintenance of location Effects 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 102000004127 Cytokines Human genes 0.000 description 8
- 108090000695 Cytokines Proteins 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 102100039364 Metalloproteinase inhibitor 1 Human genes 0.000 description 8
- 239000007983 Tris buffer Substances 0.000 description 8
- 210000004027 cell Anatomy 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- WEIBGUDKHYWNMW-UHFFFAOYSA-N tert-butyl 4-(4-aminophenoxy)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OC1=CC=C(N)C=C1 WEIBGUDKHYWNMW-UHFFFAOYSA-N 0.000 description 8
- 238000004587 chromatography analysis Methods 0.000 description 7
- 239000003480 eluent Substances 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- 229940124597 therapeutic agent Drugs 0.000 description 7
- 238000003828 vacuum filtration Methods 0.000 description 7
- RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 description 6
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 239000012634 fragment Substances 0.000 description 6
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- YAAWASYJIRZXSZ-UHFFFAOYSA-N pyrimidine-2,4-diamine Chemical compound NC1=CC=NC(N)=N1 YAAWASYJIRZXSZ-UHFFFAOYSA-N 0.000 description 6
- 102000004190 Enzymes Human genes 0.000 description 5
- 108090000790 Enzymes Proteins 0.000 description 5
- 229940122245 Janus kinase inhibitor Drugs 0.000 description 5
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 5
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 5
- 102000005789 Vascular Endothelial Growth Factors Human genes 0.000 description 5
- 108010019530 Vascular Endothelial Growth Factors Proteins 0.000 description 5
- 239000007900 aqueous suspension Substances 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 229940088598 enzyme Drugs 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 239000000796 flavoring agent Substances 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- 238000002953 preparative HPLC Methods 0.000 description 5
- 239000003755 preservative agent Substances 0.000 description 5
- 102000004169 proteins and genes Human genes 0.000 description 5
- 230000011664 signaling Effects 0.000 description 5
- 239000003765 sweetening agent Substances 0.000 description 5
- ZJAZTEBLROVTGQ-UHFFFAOYSA-N 2-chloro-4-[[5-methyl-2-[4-(2-pyrrolidin-1-ylethoxy)anilino]pyrimidin-4-yl]amino]benzonitrile Chemical compound N1=C(NC=2C=C(Cl)C(C#N)=CC=2)C(C)=CN=C1NC(C=C1)=CC=C1OCCN1CCCC1 ZJAZTEBLROVTGQ-UHFFFAOYSA-N 0.000 description 4
- FJNLCHNQVJVCPY-UHFFFAOYSA-N 2-n-methoxy-2-n-methyl-4-n,6-n-dipropyl-1,3,5-triazine-2,4,6-triamine Chemical compound CCCNC1=NC(NCCC)=NC(N(C)OC)=N1 FJNLCHNQVJVCPY-UHFFFAOYSA-N 0.000 description 4
- WEVYNIUIFUYDGI-UHFFFAOYSA-N 3-[6-[4-(trifluoromethoxy)anilino]-4-pyrimidinyl]benzamide Chemical compound NC(=O)C1=CC=CC(C=2N=CN=C(NC=3C=CC(OC(F)(F)F)=CC=3)C=2)=C1 WEVYNIUIFUYDGI-UHFFFAOYSA-N 0.000 description 4
- PGXAYGZAIAUNJP-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-2-[3-(2-pyrrolidin-1-ylethoxy)anilino]pyrimidine-5-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC(NC=2C(=CN=C(NC=3C=C(OCCN4CCCC4)C=CC=3)N=2)C#N)=C1Cl PGXAYGZAIAUNJP-UHFFFAOYSA-N 0.000 description 4
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 4
- 102100032937 CD40 ligand Human genes 0.000 description 4
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 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 4
- 101000868215 Homo sapiens CD40 ligand Proteins 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 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 4
- NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 235000003599 food sweetener Nutrition 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- PAMZSAVUMVFFRE-UHFFFAOYSA-N n-tert-butyl-3-[[5-methyl-2-(4-piperazin-1-ylanilino)pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound N1=C(NC=2C=C(C=CC=2)S(=O)(=O)NC(C)(C)C)C(C)=CN=C1NC(C=C1)=CC=C1N1CCNCC1 PAMZSAVUMVFFRE-UHFFFAOYSA-N 0.000 description 4
- 230000002035 prolonged effect Effects 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 239000000375 suspending agent Substances 0.000 description 4
- 239000006188 syrup Substances 0.000 description 4
- 235000020357 syrup Nutrition 0.000 description 4
- 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 4
- 238000002560 therapeutic procedure Methods 0.000 description 4
- WYWHKKSPHMUBEB-UHFFFAOYSA-N tioguanine Chemical compound N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 3
- OBAGQTQEJAPSAL-UHFFFAOYSA-N 2-chloro-n-(4-chloro-3-methoxyphenyl)-5-methylpyrimidin-4-amine Chemical compound C1=C(Cl)C(OC)=CC(NC=2C(=CN=C(Cl)N=2)C)=C1 OBAGQTQEJAPSAL-UHFFFAOYSA-N 0.000 description 3
- BIWRWICMBCFTTH-UHFFFAOYSA-N 3-[[5-methyl-2-[4-(2-pyrrolidin-1-ylethoxy)anilino]pyrimidin-4-yl]amino]phenol Chemical compound N1=C(NC=2C=C(O)C=CC=2)C(C)=CN=C1NC(C=C1)=CC=C1OCCN1CCCC1 BIWRWICMBCFTTH-UHFFFAOYSA-N 0.000 description 3
- XFBLKGPSFMLRFU-UHFFFAOYSA-N 3-[[5-methyl-2-[4-(4-methylpiperazin-1-yl)anilino]pyrimidin-4-yl]amino]-n-propan-2-ylbenzenesulfonamide Chemical compound CC(C)NS(=O)(=O)C1=CC=CC(NC=2C(=CN=C(NC=3C=CC(=CC=3)N3CCN(C)CC3)N=2)C)=C1 XFBLKGPSFMLRFU-UHFFFAOYSA-N 0.000 description 3
- PKTQHWKZGFKXGT-UHFFFAOYSA-N 3-bromo-n-tert-butylbenzenesulfonamide Chemical compound CC(C)(C)NS(=O)(=O)C1=CC=CC(Br)=C1 PKTQHWKZGFKXGT-UHFFFAOYSA-N 0.000 description 3
- CSNZLTNQNNWODN-UHFFFAOYSA-N 4-(1h-indol-4-ylmethyl)-5-methyl-n-[4-(2-pyrrolidin-1-ylethoxy)phenyl]pyrimidin-2-amine Chemical compound N1=C(CC=2C=3C=CNC=3C=CC=2)C(C)=CN=C1NC(C=C1)=CC=C1OCCN1CCCC1 CSNZLTNQNNWODN-UHFFFAOYSA-N 0.000 description 3
- IHFFJMRYKCVGOZ-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-2-[4-(2-pyrrolidin-1-ylethoxy)anilino]pyrimidine-5-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC(NC=2C(=CN=C(NC=3C=CC(OCCN4CCCC4)=CC=3)N=2)C#N)=C1Cl IHFFJMRYKCVGOZ-UHFFFAOYSA-N 0.000 description 3
- WNYFVEFUHMDIRQ-UHFFFAOYSA-N 4-(morpholin-4-ylmethyl)aniline Chemical compound C1=CC(N)=CC=C1CN1CCOCC1 WNYFVEFUHMDIRQ-UHFFFAOYSA-N 0.000 description 3
- VNPLQAQMVSJOAW-UHFFFAOYSA-N 4-benzyl-5-methyl-n-[4-(2-pyrrolidin-1-ylethoxy)phenyl]pyrimidin-2-amine Chemical compound N1=C(CC=2C=CC=CC=2)C(C)=CN=C1NC(C=C1)=CC=C1OCCN1CCCC1 VNPLQAQMVSJOAW-UHFFFAOYSA-N 0.000 description 3
- UAMVKOTWSHJOSY-UHFFFAOYSA-N 4-bromo-1-chloro-2-methoxybenzene Chemical compound COC1=CC(Br)=CC=C1Cl UAMVKOTWSHJOSY-UHFFFAOYSA-N 0.000 description 3
- ABBUZRXDYLQKRH-UHFFFAOYSA-N 4-bromo-7-chloro-1h-indole Chemical compound ClC1=CC=C(Br)C2=C1NC=C2 ABBUZRXDYLQKRH-UHFFFAOYSA-N 0.000 description 3
- HMRAZZGFPFMCCH-UHFFFAOYSA-N 4-isoquinolin-1-yl-5-methyl-n-[4-(2-pyrrolidin-1-ylethoxy)phenyl]pyrimidin-2-amine Chemical compound N1=C(C=2C3=CC=CC=C3C=CN=2)C(C)=CN=C1NC(C=C1)=CC=C1OCCN1CCCC1 HMRAZZGFPFMCCH-UHFFFAOYSA-N 0.000 description 3
- JKPOSEAWBGXCMP-UHFFFAOYSA-N 4-n-(2,4-dichloro-5-methoxyphenyl)-5-methyl-2-n-[3-(2-pyrrolidin-1-ylethoxy)phenyl]pyrimidine-2,4-diamine Chemical compound C1=C(Cl)C(OC)=CC(NC=2C(=CN=C(NC=3C=C(OCCN4CCCC4)C=CC=3)N=2)C)=C1Cl JKPOSEAWBGXCMP-UHFFFAOYSA-N 0.000 description 3
- HXKIWXBIBASZSX-UHFFFAOYSA-N 4-n-(4-chlorophenyl)-5-methyl-2-n-[4-(2-pyrrolidin-1-ylethoxy)phenyl]pyrimidine-2,4-diamine Chemical compound N1=C(NC=2C=CC(Cl)=CC=2)C(C)=CN=C1NC(C=C1)=CC=C1OCCN1CCCC1 HXKIWXBIBASZSX-UHFFFAOYSA-N 0.000 description 3
- CSFIQHZIFKIQNO-UHFFFAOYSA-N 4-pyrazol-1-ylaniline Chemical compound C1=CC(N)=CC=C1N1N=CC=C1 CSFIQHZIFKIQNO-UHFFFAOYSA-N 0.000 description 3
- ORRPCVFQMZHSIN-UHFFFAOYSA-N 5-methyl-2-n-[4-(2-pyrrolidin-1-ylethoxy)phenyl]-4-n-[4-(trifluoromethyl)phenyl]pyrimidine-2,4-diamine Chemical compound N1=C(NC=2C=CC(=CC=2)C(F)(F)F)C(C)=CN=C1NC(C=C1)=CC=C1OCCN1CCCC1 ORRPCVFQMZHSIN-UHFFFAOYSA-N 0.000 description 3
- LYOXDLPPWFRPBF-UHFFFAOYSA-N 5-methyl-2-n-[4-(4-methylpiperazin-1-yl)phenyl]-4-n-(3-propylsulfonylphenyl)pyrimidine-2,4-diamine;hydrochloride Chemical compound Cl.CCCS(=O)(=O)C1=CC=CC(NC=2C(=CN=C(NC=3C=CC(=CC=3)N3CCN(C)CC3)N=2)C)=C1 LYOXDLPPWFRPBF-UHFFFAOYSA-N 0.000 description 3
- HXCSWWLSBCMKJL-UHFFFAOYSA-N 5-methyl-4-n-(3-nitrophenyl)-2-n-[4-(2-pyrrolidin-1-ylethoxy)phenyl]pyrimidine-2,4-diamine Chemical compound N1=C(NC=2C=C(C=CC=2)[N+]([O-])=O)C(C)=CN=C1NC(C=C1)=CC=C1OCCN1CCCC1 HXCSWWLSBCMKJL-UHFFFAOYSA-N 0.000 description 3
- VVKAWCJISRQGDS-UHFFFAOYSA-N 5-methyl-4-n-(4-methylphenyl)-2-n-[4-(2-pyrrolidin-1-ylethoxy)phenyl]pyrimidine-2,4-diamine Chemical compound C1=CC(C)=CC=C1NC1=NC(NC=2C=CC(OCCN3CCCC3)=CC=2)=NC=C1C VVKAWCJISRQGDS-UHFFFAOYSA-N 0.000 description 3
- GXXGXOGKCKJPOF-UHFFFAOYSA-N 5-methyl-4-naphthalen-1-yl-n-[4-(2-pyrrolidin-1-ylethoxy)phenyl]pyrimidin-2-amine Chemical compound N1=C(C=2C3=CC=CC=C3C=CC=2)C(C)=CN=C1NC(C=C1)=CC=C1OCCN1CCCC1 GXXGXOGKCKJPOF-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 3
- 101150013553 CD40 gene Proteins 0.000 description 3
- PTOAARAWEBMLNO-KVQBGUIXSA-N Cladribine Chemical compound C1=NC=2C(N)=NC(Cl)=NC=2N1[C@H]1C[C@H](O)[C@@H](CO)O1 PTOAARAWEBMLNO-KVQBGUIXSA-N 0.000 description 3
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 3
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 3
- 108010092160 Dactinomycin Proteins 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 101000759376 Escherichia phage Mu Tail sheath protein Proteins 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 101000997832 Homo sapiens Tyrosine-protein kinase JAK2 Proteins 0.000 description 3
- XDXDZDZNSLXDNA-TZNDIEGXSA-N Idarubicin Chemical compound C1[C@H](N)[C@H](O)[C@H](C)O[C@H]1O[C@@H]1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2C[C@@](O)(C(C)=O)C1 XDXDZDZNSLXDNA-TZNDIEGXSA-N 0.000 description 3
- 102000000588 Interleukin-2 Human genes 0.000 description 3
- 108010002350 Interleukin-2 Proteins 0.000 description 3
- ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 3
- 229930006000 Sucrose Natural products 0.000 description 3
- 102100040245 Tumor necrosis factor receptor superfamily member 5 Human genes 0.000 description 3
- 102100033444 Tyrosine-protein kinase JAK2 Human genes 0.000 description 3
- RJURFGZVJUQBHK-IIXSONLDSA-N actinomycin D Chemical compound C[C@H]1OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C(=O)[C@@H]2CCCN2C(=O)[C@@H](C(C)C)NC(=O)[C@H]1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)N[C@@H]4C(=O)N[C@@H](C(N5CCC[C@H]5C(=O)N(C)CC(=O)N(C)[C@@H](C(C)C)C(=O)O[C@@H]4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-IIXSONLDSA-N 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 208000026935 allergic disease Diseases 0.000 description 3
- 230000000340 anti-metabolite Effects 0.000 description 3
- 229940100197 antimetabolite Drugs 0.000 description 3
- 239000002256 antimetabolite Substances 0.000 description 3
- 125000005018 aryl alkenyl group Chemical group 0.000 description 3
- 125000005015 aryl alkynyl group Chemical group 0.000 description 3
- 125000000732 arylene group Chemical group 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 230000004663 cell proliferation Effects 0.000 description 3
- 230000001413 cellular effect Effects 0.000 description 3
- 239000007810 chemical reaction solvent Substances 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 229960004397 cyclophosphamide Drugs 0.000 description 3
- 229960000640 dactinomycin Drugs 0.000 description 3
- STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin 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(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- ODKNJVUHOIMIIZ-RRKCRQDMSA-N floxuridine Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(F)=C1 ODKNJVUHOIMIIZ-RRKCRQDMSA-N 0.000 description 3
- 229960000961 floxuridine Drugs 0.000 description 3
- 235000013355 food flavoring agent Nutrition 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 239000003102 growth factor Substances 0.000 description 3
- 230000009610 hypersensitivity Effects 0.000 description 3
- 238000012423 maintenance Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229960004961 mechlorethamine Drugs 0.000 description 3
- GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 description 3
- 229960000485 methotrexate Drugs 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- VMOCPYUWQJQMBY-UHFFFAOYSA-N n-tert-butyl-3-[[2-[4-(imidazol-1-ylmethyl)anilino]-5-methylpyrimidin-4-yl]amino]benzenesulfonamide Chemical compound N1=C(NC=2C=C(C=CC=2)S(=O)(=O)NC(C)(C)C)C(C)=CN=C1NC(C=C1)=CC=C1CN1C=CN=C1 VMOCPYUWQJQMBY-UHFFFAOYSA-N 0.000 description 3
- FMMYMBAPEYABDU-UHFFFAOYSA-N n-tert-butyl-3-[[5-methyl-2-(3-piperazin-1-ylanilino)pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound N1=C(NC=2C=C(C=CC=2)S(=O)(=O)NC(C)(C)C)C(C)=CN=C1NC(C=1)=CC=CC=1N1CCNCC1 FMMYMBAPEYABDU-UHFFFAOYSA-N 0.000 description 3
- MMXZBJJTHQWMEN-UHFFFAOYSA-N n-tert-butyl-3-[[5-methyl-2-[4-(morpholin-4-ylmethyl)anilino]pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound N1=C(NC=2C=C(C=CC=2)S(=O)(=O)NC(C)(C)C)C(C)=CN=C1NC(C=C1)=CC=C1CN1CCOCC1 MMXZBJJTHQWMEN-UHFFFAOYSA-N 0.000 description 3
- TVOXLCMONHSUAC-UHFFFAOYSA-N n-tert-butyl-3-[[5-methyl-2-[4-(pyridin-4-ylmethyl)anilino]pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound N1=C(NC=2C=C(C=CC=2)S(=O)(=O)NC(C)(C)C)C(C)=CN=C1NC(C=C1)=CC=C1CC1=CC=NC=C1 TVOXLCMONHSUAC-UHFFFAOYSA-N 0.000 description 3
- 231100000252 nontoxic Toxicity 0.000 description 3
- 230000003000 nontoxic effect Effects 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 108090000765 processed proteins & peptides Proteins 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 238000005488 sandblasting Methods 0.000 description 3
- 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 3
- 239000003381 stabilizer Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000007920 subcutaneous administration Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000005720 sucrose Substances 0.000 description 3
- 230000008685 targeting Effects 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- 238000002054 transplantation Methods 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 2
- FMCAFXHLMUOIGG-JTJHWIPRSA-N (2s)-2-[[(2r)-2-[[(2s)-2-[[(2r)-2-formamido-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,5-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound O=CN[C@@H](CS)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(=O)N[C@@H](CCSC)C(O)=O)CC1=CC(C)=C(O)C=C1C FMCAFXHLMUOIGG-JTJHWIPRSA-N 0.000 description 2
- FMCAFXHLMUOIGG-IWFBPKFRSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-formamido-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,5-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound O=CN[C@@H](CS)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCSC)C(O)=O)CC1=CC(C)=C(O)C=C1C FMCAFXHLMUOIGG-IWFBPKFRSA-N 0.000 description 2
- ZXHMUQVMGJYGAV-UHFFFAOYSA-N (4-bromoindol-1-yl)-tri(propan-2-yl)silane Chemical compound C1=CC=C2N([Si](C(C)C)(C(C)C)C(C)C)C=CC2=C1Br ZXHMUQVMGJYGAV-UHFFFAOYSA-N 0.000 description 2
- FPVKHBSQESCIEP-UHFFFAOYSA-N (8S)-3-(2-deoxy-beta-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol Natural products C1C(O)C(CO)OC1N1C(NC=NCC2O)=C2N=C1 FPVKHBSQESCIEP-UHFFFAOYSA-N 0.000 description 2
- IAKHMKGGTNLKSZ-INIZCTEOSA-N (S)-colchicine Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(OC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC IAKHMKGGTNLKSZ-INIZCTEOSA-N 0.000 description 2
- 102100025573 1-alkyl-2-acetylglycerophosphocholine esterase Human genes 0.000 description 2
- SJIIFORJBWPNPM-UHFFFAOYSA-N 1-bromo-2,4-dichloro-5-methoxybenzene Chemical compound COC1=CC(Br)=C(Cl)C=C1Cl SJIIFORJBWPNPM-UHFFFAOYSA-N 0.000 description 2
- FDXXHPYFJDKWJS-UHFFFAOYSA-N 1-bromo-3-tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC(Br)=C1 FDXXHPYFJDKWJS-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
- OYUQCQCQLDTRHQ-UHFFFAOYSA-N 2,4-diaminopyrimidine-5-carbonitrile Chemical compound NC1=NC=C(C#N)C(N)=N1 OYUQCQCQLDTRHQ-UHFFFAOYSA-N 0.000 description 2
- SRCAKTIYISIAIT-UHFFFAOYSA-N 2-(4-aminophenoxy)ethanol Chemical compound NC1=CC=C(OCCO)C=C1 SRCAKTIYISIAIT-UHFFFAOYSA-N 0.000 description 2
- YAPAEYFBLRVUMH-UHFFFAOYSA-N 2-(4-nitrophenoxy)ethanol Chemical compound OCCOC1=CC=C([N+]([O-])=O)C=C1 YAPAEYFBLRVUMH-UHFFFAOYSA-N 0.000 description 2
- YLYPIBBGWLKELC-RMKNXTFCSA-N 2-[2-[(e)-2-[4-(dimethylamino)phenyl]ethenyl]-6-methylpyran-4-ylidene]propanedinitrile Chemical compound C1=CC(N(C)C)=CC=C1\C=C\C1=CC(=C(C#N)C#N)C=C(C)O1 YLYPIBBGWLKELC-RMKNXTFCSA-N 0.000 description 2
- XLLBDOWZYVOHON-UHFFFAOYSA-N 2-[4-[[4-(4-chloro-3-methoxyanilino)-5-methylpyrimidin-2-yl]amino]phenoxy]ethanol Chemical compound C1=C(Cl)C(OC)=CC(NC=2C(=CN=C(NC=3C=CC(OCCO)=CC=3)N=2)C)=C1 XLLBDOWZYVOHON-UHFFFAOYSA-N 0.000 description 2
- MZRPZVNKNDOJME-UHFFFAOYSA-N 2-[5-[[4-(1,3-benzodioxol-4-ylamino)-5-methylpyrimidin-2-yl]amino]pyridin-2-yl]oxyethanol Chemical compound N1=C(NC=2C=3OCOC=3C=CC=2)C(C)=CN=C1NC1=CC=C(OCCO)N=C1 MZRPZVNKNDOJME-UHFFFAOYSA-N 0.000 description 2
- IZHVBANLECCAGF-UHFFFAOYSA-N 2-hydroxy-3-(octadecanoyloxy)propyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCCCC IZHVBANLECCAGF-UHFFFAOYSA-N 0.000 description 2
- ZLDCKZARSORMIE-UHFFFAOYSA-N 2-methyl-3-[[5-methyl-2-[4-(4-methylpiperazin-1-yl)anilino]pyrimidin-4-yl]amino]benzamide Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C)C(NC=2C(=C(C(N)=O)C=CC=2)C)=N1 ZLDCKZARSORMIE-UHFFFAOYSA-N 0.000 description 2
- NDMPLJNOPCLANR-UHFFFAOYSA-N 3,4-dihydroxy-15-(4-hydroxy-18-methoxycarbonyl-5,18-seco-ibogamin-18-yl)-16-methoxy-1-methyl-6,7-didehydro-aspidospermidine-3-carboxylic acid methyl ester Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 NDMPLJNOPCLANR-UHFFFAOYSA-N 0.000 description 2
- IAXMYIMAOOVYIT-UHFFFAOYSA-N 3-[[2-[4-(4-acetylpiperazin-1-yl)-3-(trifluoromethyl)anilino]-5-methylpyrimidin-4-yl]amino]-n-tert-butylbenzenesulfonamide Chemical compound C1CN(C(=O)C)CCN1C(C(=C1)C(F)(F)F)=CC=C1NC1=NC=C(C)C(NC=2C=C(C=CC=2)S(=O)(=O)NC(C)(C)C)=N1 IAXMYIMAOOVYIT-UHFFFAOYSA-N 0.000 description 2
- HTBQLLWSEHTXBY-UHFFFAOYSA-N 3-[[2-[4-(4-acetylpiperazin-1-yl)anilino]-5-methylpyrimidin-4-yl]amino]-n-tert-butylbenzenesulfonamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C)C(NC=2C=C(C=CC=2)S(=O)(=O)NC(C)(C)C)=N1 HTBQLLWSEHTXBY-UHFFFAOYSA-N 0.000 description 2
- CWVNGUSSWBTKNM-UHFFFAOYSA-N 3-[[5-methyl-2-[4-(2-pyrrolidin-1-ylethoxy)anilino]pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound N1=C(NC=2C=C(C=CC=2)S(N)(=O)=O)C(C)=CN=C1NC(C=C1)=CC=C1OCCN1CCCC1 CWVNGUSSWBTKNM-UHFFFAOYSA-N 0.000 description 2
- VJEGPQDOUQQMNB-UHFFFAOYSA-N 3-[[5-methyl-2-[4-(4-methylpiperazin-1-yl)anilino]pyrimidin-4-yl]amino]-n-piperidin-4-ylbenzenesulfonamide Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C)C(NC=2C=C(C=CC=2)S(=O)(=O)NC2CCNCC2)=N1 VJEGPQDOUQQMNB-UHFFFAOYSA-N 0.000 description 2
- YBNPCJSZMYHDDR-UHFFFAOYSA-N 3-bromo-n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC(Br)=C1 YBNPCJSZMYHDDR-UHFFFAOYSA-N 0.000 description 2
- MUBJNMWVQGHHLG-UHFFFAOYSA-N 3-bromobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC(Br)=C1 MUBJNMWVQGHHLG-UHFFFAOYSA-N 0.000 description 2
- HNGQQUDFJDROPY-UHFFFAOYSA-N 3-bromobenzenethiol Chemical compound SC1=CC=CC(Br)=C1 HNGQQUDFJDROPY-UHFFFAOYSA-N 0.000 description 2
- KGNACZCVKXGKEX-UHFFFAOYSA-N 4-(1-morpholin-4-ylethyl)aniline Chemical compound C=1C=C(N)C=CC=1C(C)N1CCOCC1 KGNACZCVKXGKEX-UHFFFAOYSA-N 0.000 description 2
- IEZCMVRWKNEHJB-UHFFFAOYSA-N 4-(2-methylimidazol-1-yl)aniline Chemical compound CC1=NC=CN1C1=CC=C(N)C=C1 IEZCMVRWKNEHJB-UHFFFAOYSA-N 0.000 description 2
- ISRYTHBRUSOVAB-UHFFFAOYSA-N 4-(pyrazol-1-ylmethyl)aniline Chemical compound C1=CC(N)=CC=C1CN1N=CC=C1 ISRYTHBRUSOVAB-UHFFFAOYSA-N 0.000 description 2
- NIXCVBFXLJWUTC-UHFFFAOYSA-N 4-[(4-methylpiperazin-1-yl)methyl]aniline Chemical compound C1CN(C)CCN1CC1=CC=C(N)C=C1 NIXCVBFXLJWUTC-UHFFFAOYSA-N 0.000 description 2
- AFQQCFNNGLIUPF-UHFFFAOYSA-N 4-[4-chloro-3-(trifluoromethyl)phenyl]-5-methyl-2-N-(4-piperidin-4-yloxyphenyl)-1H-pyrimidine-2,4-diamine Chemical compound ClC1=C(C=C(C=C1)C1(NC(=NC=C1C)NC1=CC=C(C=C1)OC1CCNCC1)N)C(F)(F)F AFQQCFNNGLIUPF-UHFFFAOYSA-N 0.000 description 2
- GRJZJFUBQYULKL-UHFFFAOYSA-N 4-bromo-1h-indole Chemical compound BrC1=CC=CC2=C1C=CN2 GRJZJFUBQYULKL-UHFFFAOYSA-N 0.000 description 2
- FEMJIOSKNKIMBM-UHFFFAOYSA-N 4-bromo-7-methyl-1h-indole Chemical compound CC1=CC=C(Br)C2=C1NC=C2 FEMJIOSKNKIMBM-UHFFFAOYSA-N 0.000 description 2
- LVOASPZGXNAHJI-UHFFFAOYSA-N 4-imidazol-1-ylaniline Chemical compound C1=CC(N)=CC=C1N1C=NC=C1 LVOASPZGXNAHJI-UHFFFAOYSA-N 0.000 description 2
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 2
- PHNDZBFLOPIMSM-UHFFFAOYSA-N 4-morpholin-4-ylaniline Chemical compound C1=CC(N)=CC=C1N1CCOCC1 PHNDZBFLOPIMSM-UHFFFAOYSA-N 0.000 description 2
- KUPNNDWIFOCGCH-UHFFFAOYSA-N 4-n-(1,3-benzodioxol-4-yl)-5-methyl-2-n-[4-(2-pyrrolidin-1-ylethoxy)phenyl]pyrimidine-2,4-diamine Chemical compound N1=C(NC=2C=3OCOC=3C=CC=2)C(C)=CN=C1NC(C=C1)=CC=C1OCCN1CCCC1 KUPNNDWIFOCGCH-UHFFFAOYSA-N 0.000 description 2
- DTEVLQQJCOJZQQ-UHFFFAOYSA-N 4-n-(2,3-dimethylphenyl)-5-methyl-2-n-(4-piperidin-4-yloxyphenyl)pyrimidine-2,4-diamine Chemical compound CC1=CC=CC(NC=2C(=CN=C(NC=3C=CC(OC4CCNCC4)=CC=3)N=2)C)=C1C DTEVLQQJCOJZQQ-UHFFFAOYSA-N 0.000 description 2
- XWWBYPASWTXKIU-UHFFFAOYSA-N 4-n-(3,5-dimethoxyphenyl)-5-methyl-2-n-(4-piperidin-4-yloxyphenyl)pyrimidine-2,4-diamine Chemical compound COC1=CC(OC)=CC(NC=2C(=CN=C(NC=3C=CC(OC4CCNCC4)=CC=3)N=2)C)=C1 XWWBYPASWTXKIU-UHFFFAOYSA-N 0.000 description 2
- VIIOFZLRBQHXAE-UHFFFAOYSA-N 4-n-(3-tert-butylphenyl)-5-methyl-2-n-(4-piperidin-4-yloxyphenyl)pyrimidine-2,4-diamine Chemical compound N1=C(NC=2C=C(C=CC=2)C(C)(C)C)C(C)=CN=C1NC(C=C1)=CC=C1OC1CCNCC1 VIIOFZLRBQHXAE-UHFFFAOYSA-N 0.000 description 2
- OUWFWVYECBUKEG-UHFFFAOYSA-N 4-n-(3-tert-butylphenyl)-5-methyl-2-n-(4-pyrazol-1-ylphenyl)pyrimidine-2,4-diamine Chemical compound N1=C(NC=2C=C(C=CC=2)C(C)(C)C)C(C)=CN=C1NC(C=C1)=CC=C1N1C=CC=N1 OUWFWVYECBUKEG-UHFFFAOYSA-N 0.000 description 2
- WXESPIPMHZLVQR-UHFFFAOYSA-N 4-n-(3-tert-butylphenyl)-5-methyl-2-n-[4-(2-pyrrolidin-1-ylethoxy)phenyl]pyrimidine-2,4-diamine Chemical compound N1=C(NC=2C=C(C=CC=2)C(C)(C)C)C(C)=CN=C1NC(C=C1)=CC=C1OCCN1CCCC1 WXESPIPMHZLVQR-UHFFFAOYSA-N 0.000 description 2
- YFJBAFITPLIRCH-UHFFFAOYSA-N 4-n-(4-chloro-3,5-dimethylphenyl)-5-methyl-2-n-[4-(4-methylpiperazin-1-yl)phenyl]pyrimidine-2,4-diamine Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C)C(NC=2C=C(C)C(Cl)=C(C)C=2)=N1 YFJBAFITPLIRCH-UHFFFAOYSA-N 0.000 description 2
- KTNSSHYTKKTWLR-UHFFFAOYSA-N 4-n-(4-chloro-3-fluorophenyl)-5-methyl-2-n-[4-(2-pyrrolidin-1-ylethoxy)phenyl]pyrimidine-2,4-diamine Chemical compound N1=C(NC=2C=C(F)C(Cl)=CC=2)C(C)=CN=C1NC(C=C1)=CC=C1OCCN1CCCC1 KTNSSHYTKKTWLR-UHFFFAOYSA-N 0.000 description 2
- YGDNWJFREUCYCN-UHFFFAOYSA-N 4-n-(4-chloro-3-methoxyphenyl)-5-methyl-2-n-(4-morpholin-4-ylphenyl)pyrimidine-2,4-diamine Chemical compound C1=C(Cl)C(OC)=CC(NC=2C(=CN=C(NC=3C=CC(=CC=3)N3CCOCC3)N=2)C)=C1 YGDNWJFREUCYCN-UHFFFAOYSA-N 0.000 description 2
- HFNKGTWZMDUXRJ-UHFFFAOYSA-N 4-n-(4-chloro-3-methoxyphenyl)-5-methyl-2-n-(4-piperazin-1-ylphenyl)pyrimidine-2,4-diamine Chemical compound C1=C(Cl)C(OC)=CC(NC=2C(=CN=C(NC=3C=CC(=CC=3)N3CCNCC3)N=2)C)=C1 HFNKGTWZMDUXRJ-UHFFFAOYSA-N 0.000 description 2
- PXJHVWRFCBMFLZ-UHFFFAOYSA-N 4-n-(4-chloro-3-methoxyphenyl)-5-methyl-2-n-[3-(piperazin-1-ylmethyl)phenyl]pyrimidine-2,4-diamine Chemical compound C1=C(Cl)C(OC)=CC(NC=2C(=CN=C(NC=3C=C(CN4CCNCC4)C=CC=3)N=2)C)=C1 PXJHVWRFCBMFLZ-UHFFFAOYSA-N 0.000 description 2
- CCPRZWXORCAPHA-UHFFFAOYSA-N 4-n-(4-chloro-3-methoxyphenyl)-5-methyl-2-n-[4-(piperazin-1-ylmethyl)phenyl]pyrimidine-2,4-diamine Chemical compound C1=C(Cl)C(OC)=CC(NC=2C(=CN=C(NC=3C=CC(CN4CCNCC4)=CC=3)N=2)C)=C1 CCPRZWXORCAPHA-UHFFFAOYSA-N 0.000 description 2
- ULTWGBXFMNBZEA-UHFFFAOYSA-N 4-n-[3-(2,5-dimethylpyrrolidin-1-yl)sulfonylphenyl]-5-methyl-2-n-[4-(4-methylpiperazin-1-yl)phenyl]pyrimidine-2,4-diamine Chemical compound CC1CCC(C)N1S(=O)(=O)C1=CC=CC(NC=2C(=CN=C(NC=3C=CC(=CC=3)N3CCN(C)CC3)N=2)C)=C1 ULTWGBXFMNBZEA-UHFFFAOYSA-N 0.000 description 2
- VQZFMKHDXZYMMZ-UHFFFAOYSA-N 5-methyl-2-N-[4-(4-methylpiperazin-1-yl)phenyl]-4-N-[3-methyl-4-(trifluoromethyl)phenyl]pyrimidine-2,4-diamine hydrochloride Chemical compound Cl.C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C)C(NC=2C=C(C)C(=CC=2)C(F)(F)F)=N1 VQZFMKHDXZYMMZ-UHFFFAOYSA-N 0.000 description 2
- WJVVIFQPFZUMNL-UHFFFAOYSA-N 5-methyl-2-n-[4-(2-pyrrolidin-1-ylethoxy)phenyl]-4-n-[3-(trifluoromethyl)phenyl]pyrimidine-2,4-diamine Chemical compound N1=C(NC=2C=C(C=CC=2)C(F)(F)F)C(C)=CN=C1NC(C=C1)=CC=C1OCCN1CCCC1 WJVVIFQPFZUMNL-UHFFFAOYSA-N 0.000 description 2
- BLMVITRKCQFTHW-UHFFFAOYSA-N 5-methyl-2-n-[4-(2-pyrrolidin-1-ylethoxy)phenyl]pyrimidine-2,4-diamine Chemical compound N1=C(N)C(C)=CN=C1NC(C=C1)=CC=C1OCCN1CCCC1 BLMVITRKCQFTHW-UHFFFAOYSA-N 0.000 description 2
- FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 description 2
- VKTQCNBLDIOWTR-UHFFFAOYSA-N 6-(1,3-dioxol-4-yl)-5-methyl-2-N-[4-(2-pyrrolidin-1-ylethoxy)phenyl]pyrimidine-2,4-diamine Chemical compound O1COC=C1C1=C(C(=NC(=N1)NC1=CC=C(C=C1)OCCN1CCCC1)N)C VKTQCNBLDIOWTR-UHFFFAOYSA-N 0.000 description 2
- BVLUMTVZJPNDJU-UHFFFAOYSA-N 6-(1,3-dioxol-4-yl)-5-methyl-2-N-[4-(4-methylpiperazin-1-yl)phenyl]pyrimidine-2,4-diamine Chemical compound O1COC(=C1)C1=C(C(=NC(=N1)NC1=CC=C(C=C1)N1CCN(CC1)C)N)C BVLUMTVZJPNDJU-UHFFFAOYSA-N 0.000 description 2
- STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- 206010003210 Arteriosclerosis Diseases 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 108010024976 Asparaginase Proteins 0.000 description 2
- 206010003645 Atopy Diseases 0.000 description 2
- 229910015845 BBr3 Inorganic materials 0.000 description 2
- 241000283690 Bos taurus Species 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 102100029391 Cardiotrophin-like cytokine factor 1 Human genes 0.000 description 2
- 101710107109 Cardiotrophin-like cytokine factor 1 Proteins 0.000 description 2
- DLGOEMSEDOSKAD-UHFFFAOYSA-N Carmustine Chemical compound ClCCNC(=O)N(N=O)CCCl DLGOEMSEDOSKAD-UHFFFAOYSA-N 0.000 description 2
- UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- 230000004568 DNA-binding Effects 0.000 description 2
- 241000283086 Equidae Species 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-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
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- XDXDZDZNSLXDNA-UHFFFAOYSA-N Idarubicin Natural products C1C(N)C(O)C(C)OC1OC1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2CC(O)(C(C)=O)C1 XDXDZDZNSLXDNA-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 108010050904 Interferons Proteins 0.000 description 2
- 102000014150 Interferons Human genes 0.000 description 2
- 108010065805 Interleukin-12 Proteins 0.000 description 2
- 102100030703 Interleukin-22 Human genes 0.000 description 2
- 108010002386 Interleukin-3 Proteins 0.000 description 2
- 108090000978 Interleukin-4 Proteins 0.000 description 2
- 108010002616 Interleukin-5 Proteins 0.000 description 2
- 108090001005 Interleukin-6 Proteins 0.000 description 2
- 102000004889 Interleukin-6 Human genes 0.000 description 2
- 102000015696 Interleukins Human genes 0.000 description 2
- 108010063738 Interleukins Proteins 0.000 description 2
- 208000003456 Juvenile Arthritis Diseases 0.000 description 2
- 206010059176 Juvenile idiopathic arthritis Diseases 0.000 description 2
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 2
- GQYIWUVLTXOXAJ-UHFFFAOYSA-N Lomustine Chemical compound ClCCN(N=O)C(=O)NC1CCCCC1 GQYIWUVLTXOXAJ-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 101100369199 Methanopyrus kandleri (strain AV19 / DSM 6324 / JCM 9639 / NBRC 100938) tfe gene Proteins 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 241001529936 Murinae Species 0.000 description 2
- JOOXLOJCABQBSG-UHFFFAOYSA-N N-tert-butyl-3-[[5-methyl-2-[4-[2-(1-pyrrolidinyl)ethoxy]anilino]-4-pyrimidinyl]amino]benzenesulfonamide Chemical compound N1=C(NC=2C=C(C=CC=2)S(=O)(=O)NC(C)(C)C)C(C)=CN=C1NC(C=C1)=CC=C1OCCN1CCCC1 JOOXLOJCABQBSG-UHFFFAOYSA-N 0.000 description 2
- IOIBMYFJPQDSRR-UHFFFAOYSA-N OCCN1CCN(CC1)C1=CC=C(C=C1)NC1=C(C=CC=C1NC1=NC=NC=C1C)S(=O)(=O)N Chemical compound OCCN1CCN(CC1)C1=CC=C(C=C1)NC1=C(C=CC=C1NC1=NC=NC=C1C)S(=O)(=O)N IOIBMYFJPQDSRR-UHFFFAOYSA-N 0.000 description 2
- NVNBPVZTVRBOGP-UHFFFAOYSA-N OCCN1CCN(CC1)C=1C=C(C=CC=1)NC1=C(C=CC=C1NC1=NC=NC=C1C)S(=O)(=O)N Chemical compound OCCN1CCN(CC1)C=1C=C(C=CC=1)NC1=C(C=CC=C1NC1=NC=NC=C1C)S(=O)(=O)N NVNBPVZTVRBOGP-UHFFFAOYSA-N 0.000 description 2
- 229930012538 Paclitaxel Natural products 0.000 description 2
- 235000019483 Peanut oil Nutrition 0.000 description 2
- 241001494479 Pecora Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 108010009341 Protein Serine-Threonine Kinases Proteins 0.000 description 2
- 102000009516 Protein Serine-Threonine Kinases Human genes 0.000 description 2
- YDWKSSWZGXRQET-UHFFFAOYSA-N Pyrrolidine, 1-[2-(4-bromophenoxy)ethyl]- Chemical compound C1=CC(Br)=CC=C1OCCN1CCCC1 YDWKSSWZGXRQET-UHFFFAOYSA-N 0.000 description 2
- 208000025747 Rheumatic disease Diseases 0.000 description 2
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 description 2
- 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 2
- 230000009471 action Effects 0.000 description 2
- 229930013930 alkaloid Natural products 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- YBBLVLTVTVSKRW-UHFFFAOYSA-N anastrozole Chemical compound N#CC(C)(C)C1=CC(C(C)(C#N)C)=CC(CN2N=CN=C2)=C1 YBBLVLTVTVSKRW-UHFFFAOYSA-N 0.000 description 2
- 239000002870 angiogenesis inducing agent Substances 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 229940045799 anthracyclines and related substance Drugs 0.000 description 2
- 230000003432 anti-folate effect Effects 0.000 description 2
- 229940127074 antifolate Drugs 0.000 description 2
- 208000011775 arteriosclerosis disease Diseases 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-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
- 239000002585 base Substances 0.000 description 2
- 230000027455 binding Effects 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 235000010216 calcium carbonate Nutrition 0.000 description 2
- 239000001506 calcium phosphate Substances 0.000 description 2
- 229910000389 calcium phosphate Inorganic materials 0.000 description 2
- 235000011010 calcium phosphates Nutrition 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 229960004562 carboplatin Drugs 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 229960005243 carmustine Drugs 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000024245 cell differentiation Effects 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 229960004316 cisplatin Drugs 0.000 description 2
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 230000002596 correlated effect Effects 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 108010057085 cytokine receptors Proteins 0.000 description 2
- 102000003675 cytokine receptors Human genes 0.000 description 2
- OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 description 2
- 239000008121 dextrose Substances 0.000 description 2
- 208000037765 diseases and disorders Diseases 0.000 description 2
- 229960003668 docetaxel Drugs 0.000 description 2
- 229960004679 doxorubicin Drugs 0.000 description 2
- 230000008482 dysregulation Effects 0.000 description 2
- 230000003511 endothelial effect Effects 0.000 description 2
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 2
- VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000004052 folic acid antagonist Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 229960002706 gusperimus Drugs 0.000 description 2
- 229940093915 gynecological organic acid Drugs 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 229960000908 idarubicin Drugs 0.000 description 2
- 239000012729 immediate-release (IR) formulation Substances 0.000 description 2
- 230000008629 immune suppression Effects 0.000 description 2
- 210000000987 immune system Anatomy 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 229940047124 interferons Drugs 0.000 description 2
- 229940047122 interleukins Drugs 0.000 description 2
- 238000007918 intramuscular administration Methods 0.000 description 2
- 238000007913 intrathecal administration Methods 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 230000000670 limiting effect Effects 0.000 description 2
- 229940057995 liquid paraffin Drugs 0.000 description 2
- 229960002247 lomustine Drugs 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- HAWPXGHAZFHHAD-UHFFFAOYSA-N mechlorethamine Chemical compound ClCCN(C)CCCl HAWPXGHAZFHHAD-UHFFFAOYSA-N 0.000 description 2
- 230000001404 mediated effect Effects 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- AGJSNMGHAVDLRQ-HUUJSLGLSA-N methyl (2s)-2-[[(2r)-2-[[(2s)-2-[[(2r)-2-amino-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,3-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoate Chemical compound SC[C@H](N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(=O)N[C@@H](CCSC)C(=O)OC)CC1=CC=C(O)C(C)=C1C AGJSNMGHAVDLRQ-HUUJSLGLSA-N 0.000 description 2
- AGJSNMGHAVDLRQ-IWFBPKFRSA-N methyl (2s)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-amino-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,3-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoate Chemical compound SC[C@H](N)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCSC)C(=O)OC)CC1=CC=C(O)C(C)=C1C AGJSNMGHAVDLRQ-IWFBPKFRSA-N 0.000 description 2
- WMYCQEOUYZUEAO-UHFFFAOYSA-N methyl 5-[[4-(4-chloro-3-methoxyanilino)-5-methylpyrimidin-2-yl]amino]-2-piperazin-1-ylbenzoate Chemical compound C=1C=C(N2CCNCC2)C(C(=O)OC)=CC=1NC(N=1)=NC=C(C)C=1NC1=CC=C(Cl)C(OC)=C1 WMYCQEOUYZUEAO-UHFFFAOYSA-N 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
- CFCUWKMKBJTWLW-BKHRDMLASA-N mithramycin Chemical compound O([C@@H]1C[C@@H](O[C@H](C)[C@H]1O)OC=1C=C2C=C3C[C@H]([C@@H](C(=O)C3=C(O)C2=C(O)C=1C)O[C@@H]1O[C@H](C)[C@@H](O)[C@H](O[C@@H]2O[C@H](C)[C@H](O)[C@H](O[C@@H]3O[C@H](C)[C@@H](O)[C@@](C)(O)C3)C2)C1)[C@H](OC)C(=O)[C@@H](O)[C@@H](C)O)[C@H]1C[C@@H](O)[C@H](O)[C@@H](C)O1 CFCUWKMKBJTWLW-BKHRDMLASA-N 0.000 description 2
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 2
- PMRBEMOZLRBUHH-UHFFFAOYSA-N n,2-dimethyl-5-[[5-methyl-2-[4-(2-pyrrolidin-1-ylethoxy)anilino]pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound C1=C(C)C(S(=O)(=O)NC)=CC(NC=2C(=CN=C(NC=3C=CC(OCCN4CCCC4)=CC=3)N=2)C)=C1 PMRBEMOZLRBUHH-UHFFFAOYSA-N 0.000 description 2
- UDWBXLLMIZMOJY-UHFFFAOYSA-N n,n-diethyl-3-[[5-methyl-2-[4-(4-methylpiperazin-1-yl)anilino]pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound CCN(CC)S(=O)(=O)C1=CC=CC(NC=2C(=CN=C(NC=3C=CC(=CC=3)N3CCN(C)CC3)N=2)C)=C1 UDWBXLLMIZMOJY-UHFFFAOYSA-N 0.000 description 2
- DQVJZRWCRXUJGS-UHFFFAOYSA-N n,n-dimethyl-3-[[5-methyl-2-[4-(4-methylpiperazin-1-yl)anilino]pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC=CC(NC=2C(=CN=C(NC=3C=CC(=CC=3)N3CCN(C)CC3)N=2)C)=C1 DQVJZRWCRXUJGS-UHFFFAOYSA-N 0.000 description 2
- IDINUJSAMVOPCM-INIZCTEOSA-N n-[(1s)-2-[4-(3-aminopropylamino)butylamino]-1-hydroxy-2-oxoethyl]-7-(diaminomethylideneamino)heptanamide Chemical compound NCCCNCCCCNC(=O)[C@H](O)NC(=O)CCCCCCN=C(N)N IDINUJSAMVOPCM-INIZCTEOSA-N 0.000 description 2
- POOZZJZWKACCEH-UHFFFAOYSA-N n-cyclohexyl-3-[[5-methyl-2-[4-(4-methylpiperazin-1-yl)anilino]pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C)C(NC=2C=C(C=CC=2)S(=O)(=O)NC2CCCCC2)=N1 POOZZJZWKACCEH-UHFFFAOYSA-N 0.000 description 2
- CJTYXGKPGNCYHI-UHFFFAOYSA-N n-methyl-3-[[5-methyl-2-[4-(4-methylpiperazin-1-yl)anilino]pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NC=2C(=CN=C(NC=3C=CC(=CC=3)N3CCN(C)CC3)N=2)C)=C1 CJTYXGKPGNCYHI-UHFFFAOYSA-N 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- BSEOXDZRNKMOHN-UHFFFAOYSA-N n-tert-butyl-3-[[5-methyl-2-(3-piperidin-1-ylsulfonylanilino)pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound N1=C(NC=2C=C(C=CC=2)S(=O)(=O)NC(C)(C)C)C(C)=CN=C1NC(C=1)=CC=CC=1S(=O)(=O)N1CCCCC1 BSEOXDZRNKMOHN-UHFFFAOYSA-N 0.000 description 2
- FBMIJXPDBCXJDC-UHFFFAOYSA-N n-tert-butyl-3-[[5-methyl-2-(4-morpholin-4-ylanilino)pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound N1=C(NC=2C=C(C=CC=2)S(=O)(=O)NC(C)(C)C)C(C)=CN=C1NC(C=C1)=CC=C1N1CCOCC1 FBMIJXPDBCXJDC-UHFFFAOYSA-N 0.000 description 2
- BMNRRLCVCXFPCK-UHFFFAOYSA-N n-tert-butyl-3-[[5-methyl-2-(4-piperidin-4-yloxyanilino)pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound N1=C(NC=2C=C(C=CC=2)S(=O)(=O)NC(C)(C)C)C(C)=CN=C1NC(C=C1)=CC=C1OC1CCNCC1 BMNRRLCVCXFPCK-UHFFFAOYSA-N 0.000 description 2
- KCUZPXIRHDYCKX-UHFFFAOYSA-N n-tert-butyl-3-[[5-methyl-2-(4-pyrazol-1-ylanilino)pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound N1=C(NC=2C=C(C=CC=2)S(=O)(=O)NC(C)(C)C)C(C)=CN=C1NC(C=C1)=CC=C1N1C=CC=N1 KCUZPXIRHDYCKX-UHFFFAOYSA-N 0.000 description 2
- JMEAPQPZAIUUTN-UHFFFAOYSA-N n-tert-butyl-3-[[5-methyl-2-[3-(2h-tetrazol-5-yl)anilino]pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound N1=C(NC=2C=C(C=CC=2)S(=O)(=O)NC(C)(C)C)C(C)=CN=C1NC(C=1)=CC=CC=1C1=NN=NN1 JMEAPQPZAIUUTN-UHFFFAOYSA-N 0.000 description 2
- AMPUHDKVCCLQIE-UHFFFAOYSA-N n-tert-butyl-3-[[5-methyl-2-[3-(4-methylpiperazin-1-yl)sulfonylanilino]pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound C1CN(C)CCN1S(=O)(=O)C1=CC=CC(NC=2N=C(NC=3C=C(C=CC=3)S(=O)(=O)NC(C)(C)C)C(C)=CN=2)=C1 AMPUHDKVCCLQIE-UHFFFAOYSA-N 0.000 description 2
- VDPOMIYFJDJKGW-UHFFFAOYSA-N n-tert-butyl-3-[[5-methyl-2-[3-(morpholin-4-ylmethyl)anilino]pyrimidin-4-yl]amino]benzenesulfonamide;hydrochloride Chemical compound Cl.N1=C(NC=2C=C(C=CC=2)S(=O)(=O)NC(C)(C)C)C(C)=CN=C1NC(C=1)=CC=CC=1CN1CCOCC1 VDPOMIYFJDJKGW-UHFFFAOYSA-N 0.000 description 2
- WASYPUGGFOFWBP-UHFFFAOYSA-N n-tert-butyl-3-[[5-methyl-2-[4-(1,2,4-triazol-1-ylmethyl)anilino]pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound N1=C(NC=2C=C(C=CC=2)S(=O)(=O)NC(C)(C)C)C(C)=CN=C1NC(C=C1)=CC=C1CN1C=NC=N1 WASYPUGGFOFWBP-UHFFFAOYSA-N 0.000 description 2
- XSCHAPUGUDDYED-UHFFFAOYSA-N n-tert-butyl-3-[[5-methyl-2-[4-(1-morpholin-4-ylethyl)anilino]pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound C=1C=C(NC=2N=C(NC=3C=C(C=CC=3)S(=O)(=O)NC(C)(C)C)C(C)=CN=2)C=CC=1C(C)N1CCOCC1 XSCHAPUGUDDYED-UHFFFAOYSA-N 0.000 description 2
- FSSFOACCSZOKES-UHFFFAOYSA-N n-tert-butyl-3-[[5-methyl-2-[4-(2-methylimidazol-1-yl)anilino]pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound CC1=NC=CN1C(C=C1)=CC=C1NC1=NC=C(C)C(NC=2C=C(C=CC=2)S(=O)(=O)NC(C)(C)C)=N1 FSSFOACCSZOKES-UHFFFAOYSA-N 0.000 description 2
- YAHZRVCFGOVCPM-UHFFFAOYSA-N n-tert-butyl-3-[[5-methyl-2-[4-(4-methylimidazol-1-yl)anilino]pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound C1=NC(C)=CN1C(C=C1)=CC=C1NC1=NC=C(C)C(NC=2C=C(C=CC=2)S(=O)(=O)NC(C)(C)C)=N1 YAHZRVCFGOVCPM-UHFFFAOYSA-N 0.000 description 2
- NSFSBMRSBVPJNQ-UHFFFAOYSA-N n-tert-butyl-3-[[5-methyl-2-[4-[(2-methylimidazol-1-yl)methyl]anilino]pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound CC1=NC=CN1CC(C=C1)=CC=C1NC1=NC=C(C)C(NC=2C=C(C=CC=2)S(=O)(=O)NC(C)(C)C)=N1 NSFSBMRSBVPJNQ-UHFFFAOYSA-N 0.000 description 2
- UEPGROHDLYZGCA-UHFFFAOYSA-N n-tert-butyl-5-[[2-(4-imidazol-1-ylanilino)-5-methylpyrimidin-4-yl]amino]-2-methylbenzenesulfonamide Chemical compound C1=C(S(=O)(=O)NC(C)(C)C)C(C)=CC=C1NC1=NC(NC=2C=CC(=CC=2)N2C=NC=C2)=NC=C1C UEPGROHDLYZGCA-UHFFFAOYSA-N 0.000 description 2
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 2
- 239000000346 nonvolatile oil Substances 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 239000004006 olive oil Substances 0.000 description 2
- 235000008390 olive oil Nutrition 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 230000003204 osmotic effect Effects 0.000 description 2
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
- 229960001592 paclitaxel Drugs 0.000 description 2
- 230000036961 partial effect Effects 0.000 description 2
- 239000000312 peanut oil Substances 0.000 description 2
- FPVKHBSQESCIEP-JQCXWYLXSA-N pentostatin Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(N=CNC[C@H]2O)=C2N=C1 FPVKHBSQESCIEP-JQCXWYLXSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 2
- 230000026731 phosphorylation Effects 0.000 description 2
- 238000006366 phosphorylation reaction Methods 0.000 description 2
- 229960003171 plicamycin Drugs 0.000 description 2
- 229920001184 polypeptide Polymers 0.000 description 2
- 229920000136 polysorbate Polymers 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 102000004196 processed proteins & peptides Human genes 0.000 description 2
- 229940072288 prograf Drugs 0.000 description 2
- ZAHRKKWIAAJSAO-UHFFFAOYSA-N rapamycin Natural products COCC(O)C(=C/C(C)C(=O)CC(OC(=O)C1CCCCN1C(=O)C(=O)C2(O)OC(CC(OC)C(=CC=CC=CC(C)CC(C)C(=O)C)C)CCC2C)C(C)CC3CCC(O)C(C3)OC)C ZAHRKKWIAAJSAO-UHFFFAOYSA-N 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 239000008159 sesame oil Substances 0.000 description 2
- 235000011803 sesame oil Nutrition 0.000 description 2
- 229960002930 sirolimus Drugs 0.000 description 2
- 239000001488 sodium phosphate Substances 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000005017 substituted alkenyl group Chemical group 0.000 description 2
- 125000004426 substituted alkynyl group Chemical group 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 230000004083 survival effect Effects 0.000 description 2
- 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 2
- 229960001603 tamoxifen Drugs 0.000 description 2
- NRUKOCRGYNPUPR-QBPJDGROSA-N teniposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@@H](OC[C@H]4O3)C=3SC=CC=3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 NRUKOCRGYNPUPR-QBPJDGROSA-N 0.000 description 2
- GCSOXUVISUKQBS-UHFFFAOYSA-N tert-butyl 4-(3-aminophenyl)piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1=CC=CC(N)=C1 GCSOXUVISUKQBS-UHFFFAOYSA-N 0.000 description 2
- RXFHRKPNLPBDGE-UHFFFAOYSA-N tert-butyl 4-(4-aminophenyl)piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1=CC=C(N)C=C1 RXFHRKPNLPBDGE-UHFFFAOYSA-N 0.000 description 2
- ZTYRRWNDQSVOCL-UHFFFAOYSA-N tert-butyl 4-[(4-aminophenyl)methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1CC1=CC=C(N)C=C1 ZTYRRWNDQSVOCL-UHFFFAOYSA-N 0.000 description 2
- 101150002091 tfa1 gene Proteins 0.000 description 2
- 229960003087 tioguanine Drugs 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 2
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 2
- 229960003048 vinblastine Drugs 0.000 description 2
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 2
- HHJUWIANJFBDHT-KOTLKJBCSA-N vindesine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(N)=O)N4C)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 HHJUWIANJFBDHT-KOTLKJBCSA-N 0.000 description 2
- 229960004355 vindesine Drugs 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 description 1
- MWWSFMDVAYGXBV-MYPASOLCSA-N (7r,9s)-7-[(2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione;hydrochloride Chemical compound Cl.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 MWWSFMDVAYGXBV-MYPASOLCSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- FDKXTQMXEQVLRF-ZHACJKMWSA-N (E)-dacarbazine Chemical compound CN(C)\N=N\c1[nH]cnc1C(N)=O FDKXTQMXEQVLRF-ZHACJKMWSA-N 0.000 description 1
- ZGYIXVSQHOKQRZ-COIATFDQSA-N (e)-n-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-3-cyano-7-[(3s)-oxolan-3-yl]oxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound N#CC1=CN=C2C=C(O[C@@H]3COCC3)C(NC(=O)/C=C/CN(C)C)=CC2=C1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 ZGYIXVSQHOKQRZ-COIATFDQSA-N 0.000 description 1
- MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 description 1
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- APWRZPQBPCAXFP-UHFFFAOYSA-N 1-(1-oxo-2H-isoquinolin-5-yl)-5-(trifluoromethyl)-N-[2-(trifluoromethyl)pyridin-4-yl]pyrazole-4-carboxamide Chemical compound O=C1NC=CC2=C(C=CC=C12)N1N=CC(=C1C(F)(F)F)C(=O)NC1=CC(=NC=C1)C(F)(F)F APWRZPQBPCAXFP-UHFFFAOYSA-N 0.000 description 1
- KIZGMRVDAODTGV-UHFFFAOYSA-N 1-(2-chloro-5-methylpyrimidin-4-yl)isoquinoline Chemical compound CC1=CN=C(Cl)N=C1C1=NC=CC2=CC=CC=C12 KIZGMRVDAODTGV-UHFFFAOYSA-N 0.000 description 1
- RMGFLMXDCGQKPS-UHFFFAOYSA-N 1-(2-chloroethyl)pyrrolidine Chemical compound ClCCN1CCCC1 RMGFLMXDCGQKPS-UHFFFAOYSA-N 0.000 description 1
- FSNGFFWICFYWQC-UHFFFAOYSA-N 1-(2-chloroethyl)pyrrolidine;hydron;chloride Chemical compound Cl.ClCCN1CCCC1 FSNGFFWICFYWQC-UHFFFAOYSA-N 0.000 description 1
- PMTXPOLLPCSCBE-UHFFFAOYSA-N 1-(3-bromophenyl)piperidine Chemical compound BrC1=CC=CC(N2CCCCC2)=C1 PMTXPOLLPCSCBE-UHFFFAOYSA-N 0.000 description 1
- LEUXOIBRUWVBGM-UHFFFAOYSA-N 1-(3-bromophenyl)pyrrole Chemical compound BrC1=CC=CC(N2C=CC=C2)=C1 LEUXOIBRUWVBGM-UHFFFAOYSA-N 0.000 description 1
- KSSXHPBGVNANDF-UHFFFAOYSA-N 1-(3-bromophenyl)sulfonyl-2,5-dimethylpyrrolidine Chemical compound CC1CCC(C)N1S(=O)(=O)C1=CC=CC(Br)=C1 KSSXHPBGVNANDF-UHFFFAOYSA-N 0.000 description 1
- LMHPXSVGOUBFFN-UHFFFAOYSA-N 1-(3-bromophenyl)sulfonyl-2-methylpiperidine Chemical compound CC1CCCCN1S(=O)(=O)C1=CC=CC(Br)=C1 LMHPXSVGOUBFFN-UHFFFAOYSA-N 0.000 description 1
- LUWHLKYMEKGKAT-UHFFFAOYSA-N 1-(3-bromophenyl)sulfonylpiperidine Chemical compound BrC1=CC=CC(S(=O)(=O)N2CCCCC2)=C1 LUWHLKYMEKGKAT-UHFFFAOYSA-N 0.000 description 1
- SAGKQVHXBDTCPH-UHFFFAOYSA-N 1-(3-bromophenyl)sulfonylpyrrolidine Chemical compound BrC1=CC=CC(S(=O)(=O)N2CCCC2)=C1 SAGKQVHXBDTCPH-UHFFFAOYSA-N 0.000 description 1
- DNUTZBZXLPWRJG-UHFFFAOYSA-N 1-Piperidine carboxylic acid Chemical compound OC(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-N 0.000 description 1
- ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 1
- OBPFHJKEIFNNHY-UHFFFAOYSA-N 1-[2-(2-methoxy-4-nitrophenoxy)ethyl]pyrrolidine Chemical compound COC1=CC([N+]([O-])=O)=CC=C1OCCN1CCCC1 OBPFHJKEIFNNHY-UHFFFAOYSA-N 0.000 description 1
- KMOFOKGTZRFKEM-UHFFFAOYSA-N 1-[2-(3-bromophenoxy)ethyl]pyrrolidine Chemical compound BrC1=CC=CC(OCCN2CCCC2)=C1 KMOFOKGTZRFKEM-UHFFFAOYSA-N 0.000 description 1
- AFVUJJNEILZYJQ-UHFFFAOYSA-N 1-[4-(4-aminophenyl)-1-piperazinyl]ethanone Chemical compound C1CN(C(=O)C)CCN1C1=CC=C(N)C=C1 AFVUJJNEILZYJQ-UHFFFAOYSA-N 0.000 description 1
- BLHJDWJKRCLDCC-UHFFFAOYSA-N 1-[4-[4-amino-2-(trifluoromethyl)phenyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1C1=CC=C(N)C=C1C(F)(F)F BLHJDWJKRCLDCC-UHFFFAOYSA-N 0.000 description 1
- WLPXNBYWDDYJTN-UHFFFAOYSA-N 1-bromo-2,3-dimethylbenzene Chemical compound CC1=CC=CC(Br)=C1C WLPXNBYWDDYJTN-UHFFFAOYSA-N 0.000 description 1
- OYFKTZQGAWXNTI-UHFFFAOYSA-N 1-bromo-2-methyl-3-(trifluoromethyl)benzene Chemical compound CC1=C(Br)C=CC=C1C(F)(F)F OYFKTZQGAWXNTI-UHFFFAOYSA-N 0.000 description 1
- KRWRFIMBWRVMKE-UHFFFAOYSA-N 1-bromo-3,5-dimethoxybenzene Chemical compound COC1=CC(Br)=CC(OC)=C1 KRWRFIMBWRVMKE-UHFFFAOYSA-N 0.000 description 1
- LMFRTSBQRLSJHC-UHFFFAOYSA-N 1-bromo-3,5-dimethylbenzene Chemical compound CC1=CC(C)=CC(Br)=C1 LMFRTSBQRLSJHC-UHFFFAOYSA-N 0.000 description 1
- NNMBNYHMJRJUBC-UHFFFAOYSA-N 1-bromo-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(Br)=C1 NNMBNYHMJRJUBC-UHFFFAOYSA-N 0.000 description 1
- JRGGUPZKKTVKOV-UHFFFAOYSA-N 1-bromo-3-chlorobenzene Chemical compound ClC1=CC=CC(Br)=C1 JRGGUPZKKTVKOV-UHFFFAOYSA-N 0.000 description 1
- PLDWAJLZAAHOGG-UHFFFAOYSA-N 1-bromo-3-methoxybenzene Chemical compound COC1=CC=CC(Br)=C1 PLDWAJLZAAHOGG-UHFFFAOYSA-N 0.000 description 1
- WBOMXUMQOVQNKT-UHFFFAOYSA-N 1-bromo-3-methylsulfonylbenzene Chemical compound CS(=O)(=O)C1=CC=CC(Br)=C1 WBOMXUMQOVQNKT-UHFFFAOYSA-N 0.000 description 1
- FWIROFMBWVMWLB-UHFFFAOYSA-N 1-bromo-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(Br)=C1 FWIROFMBWVMWLB-UHFFFAOYSA-N 0.000 description 1
- JSWLMTKGJQIASC-UHFFFAOYSA-N 1-bromo-3-propylsulfonylbenzene Chemical compound CCCS(=O)(=O)C1=CC=CC(Br)=C1 JSWLMTKGJQIASC-UHFFFAOYSA-N 0.000 description 1
- XLQSXGGDTHANLN-UHFFFAOYSA-N 1-bromo-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(Br)C=C1 XLQSXGGDTHANLN-UHFFFAOYSA-N 0.000 description 1
- NHDODQWIKUYWMW-UHFFFAOYSA-N 1-bromo-4-chlorobenzene Chemical compound ClC1=CC=C(Br)C=C1 NHDODQWIKUYWMW-UHFFFAOYSA-N 0.000 description 1
- ZBTMRBYMKUEVEU-UHFFFAOYSA-N 1-bromo-4-methylbenzene Chemical compound CC1=CC=C(Br)C=C1 ZBTMRBYMKUEVEU-UHFFFAOYSA-N 0.000 description 1
- DLKQHBOKULLWDQ-UHFFFAOYSA-N 1-bromonaphthalene Chemical compound C1=CC=C2C(Br)=CC=CC2=C1 DLKQHBOKULLWDQ-UHFFFAOYSA-N 0.000 description 1
- MSQCQINLJMEVNJ-UHFFFAOYSA-N 1-chloroisoquinoline Chemical compound C1=CC=C2C(Cl)=NC=CC2=C1 MSQCQINLJMEVNJ-UHFFFAOYSA-N 0.000 description 1
- WFQDTOYDVUWQMS-UHFFFAOYSA-N 1-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1 WFQDTOYDVUWQMS-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- 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
- YCWRFIYBUQBHJI-UHFFFAOYSA-N 2-(4-aminophenyl)acetonitrile Chemical group NC1=CC=C(CC#N)C=C1 YCWRFIYBUQBHJI-UHFFFAOYSA-N 0.000 description 1
- UIBDRXZQWRSOKA-UHFFFAOYSA-N 2-(5-aminopyridin-2-yl)oxyethanol Chemical compound NC1=CC=C(OCCO)N=C1 UIBDRXZQWRSOKA-UHFFFAOYSA-N 0.000 description 1
- KESQFSZFUCZCEI-UHFFFAOYSA-N 2-(5-nitropyridin-2-yl)oxyethanol Chemical compound OCCOC1=CC=C([N+]([O-])=O)C=N1 KESQFSZFUCZCEI-UHFFFAOYSA-N 0.000 description 1
- MIJDSYMOBYNHOT-UHFFFAOYSA-N 2-(ethylamino)ethanol Chemical compound CCNCCO MIJDSYMOBYNHOT-UHFFFAOYSA-N 0.000 description 1
- PNZZQMNVMMFWHW-UHFFFAOYSA-N 2-[4-(3-bromophenyl)piperidin-1-yl]ethanol Chemical compound C1CN(CCO)CCC1C1=CC=CC(Br)=C1 PNZZQMNVMMFWHW-UHFFFAOYSA-N 0.000 description 1
- MNATXMOMEVYVPO-UHFFFAOYSA-N 2-chloro-4-[(2-chloro-5-methylpyrimidin-4-yl)amino]benzonitrile Chemical compound CC1=CN=C(Cl)N=C1NC1=CC=C(C#N)C(Cl)=C1 MNATXMOMEVYVPO-UHFFFAOYSA-N 0.000 description 1
- LGDZHLUWVLZOKL-UHFFFAOYSA-N 2-chloro-5-methyl-n-(3-nitrophenyl)pyrimidin-4-amine Chemical compound CC1=CN=C(Cl)N=C1NC1=CC=CC([N+]([O-])=O)=C1 LGDZHLUWVLZOKL-UHFFFAOYSA-N 0.000 description 1
- TYBQKJBZOXMECT-UHFFFAOYSA-N 2-chloro-5-methyl-n-[4-(trifluoromethyl)phenyl]pyrimidin-4-amine Chemical compound CC1=CN=C(Cl)N=C1NC1=CC=C(C(F)(F)F)C=C1 TYBQKJBZOXMECT-UHFFFAOYSA-N 0.000 description 1
- DTYVMHJMTXFYSA-UHFFFAOYSA-N 2-chloro-5-methyl-n-naphthalen-1-ylpyrimidin-4-amine Chemical compound CC1=CN=C(Cl)N=C1NC1=CC=CC2=CC=CC=C12 DTYVMHJMTXFYSA-UHFFFAOYSA-N 0.000 description 1
- FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 description 1
- SRUOYXQNJZJCRG-UHFFFAOYSA-N 2-chloro-n-(2,4-dichloro-5-methoxyphenyl)-5-methylpyrimidin-4-amine Chemical compound C1=C(Cl)C(OC)=CC(NC=2C(=CN=C(Cl)N=2)C)=C1Cl SRUOYXQNJZJCRG-UHFFFAOYSA-N 0.000 description 1
- QRPHTLAXXXOUIF-UHFFFAOYSA-N 2-chloro-n-(3,4-dichlorophenyl)-5-methylpyrimidin-4-amine Chemical compound CC1=CN=C(Cl)N=C1NC1=CC=C(Cl)C(Cl)=C1 QRPHTLAXXXOUIF-UHFFFAOYSA-N 0.000 description 1
- QQVVBQCECZMBDI-UHFFFAOYSA-N 2-chloro-n-(3,5-dimethoxyphenyl)-5-methylpyrimidin-4-amine Chemical compound COC1=CC(OC)=CC(NC=2C(=CN=C(Cl)N=2)C)=C1 QQVVBQCECZMBDI-UHFFFAOYSA-N 0.000 description 1
- FYEZWBSZYDCHCA-UHFFFAOYSA-N 2-chloro-n-(3,5-dimethylphenyl)-5-methylpyrimidin-4-amine Chemical compound CC1=CC(C)=CC(NC=2C(=CN=C(Cl)N=2)C)=C1 FYEZWBSZYDCHCA-UHFFFAOYSA-N 0.000 description 1
- WODISICPOSYYCO-UHFFFAOYSA-N 2-chloro-n-(3-chlorophenyl)-5-methylpyrimidin-4-amine Chemical compound CC1=CN=C(Cl)N=C1NC1=CC=CC(Cl)=C1 WODISICPOSYYCO-UHFFFAOYSA-N 0.000 description 1
- FFTUQAKOQCCGNH-UHFFFAOYSA-N 2-chloro-n-(3-methoxyphenyl)-5-methylpyrimidin-4-amine Chemical compound COC1=CC=CC(NC=2C(=CN=C(Cl)N=2)C)=C1 FFTUQAKOQCCGNH-UHFFFAOYSA-N 0.000 description 1
- VPMZIKZXZUQGRU-UHFFFAOYSA-N 2-chloro-n-(4-chloro-3-fluorophenyl)-5-methylpyrimidin-4-amine Chemical compound CC1=CN=C(Cl)N=C1NC1=CC=C(Cl)C(F)=C1 VPMZIKZXZUQGRU-UHFFFAOYSA-N 0.000 description 1
- CPEAEBVWAKWXEQ-UHFFFAOYSA-N 2-chloro-n-(4-chloro-3-methoxyphenyl)-n,5-dimethylpyrimidin-4-amine Chemical compound C1=C(Cl)C(OC)=CC(N(C)C=2C(=CN=C(Cl)N=2)C)=C1 CPEAEBVWAKWXEQ-UHFFFAOYSA-N 0.000 description 1
- AVOXKMWHDSJKEV-UHFFFAOYSA-N 2-chloro-n-(4-chlorophenyl)-5-methylpyrimidin-4-amine Chemical compound CC1=CN=C(Cl)N=C1NC1=CC=C(Cl)C=C1 AVOXKMWHDSJKEV-UHFFFAOYSA-N 0.000 description 1
- PFLCSLXLQSDNBS-UHFFFAOYSA-N 2-chloro-n-[4-chloro-3-(trifluoromethyl)phenyl]-5-methylpyrimidin-4-amine Chemical compound CC1=CN=C(Cl)N=C1NC1=CC=C(Cl)C(C(F)(F)F)=C1 PFLCSLXLQSDNBS-UHFFFAOYSA-N 0.000 description 1
- WRXNJTBODVGDRY-UHFFFAOYSA-N 2-pyrrolidin-1-ylethanamine Chemical compound NCCN1CCCC1 WRXNJTBODVGDRY-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 1
- YJDXLUSVVAGFFS-UHFFFAOYSA-N 3-(2-pyrrolidin-1-ylethoxy)aniline Chemical compound NC1=CC=CC(OCCN2CCCC2)=C1 YJDXLUSVVAGFFS-UHFFFAOYSA-N 0.000 description 1
- FLGISLVJQPPAMV-UHFFFAOYSA-N 3-(2h-tetrazol-5-yl)aniline Chemical compound NC1=CC=CC(C2=NNN=N2)=C1 FLGISLVJQPPAMV-UHFFFAOYSA-N 0.000 description 1
- BYHQTRFJOGIQAO-GOSISDBHSA-N 3-(4-bromophenyl)-8-[(2R)-2-hydroxypropyl]-1-[(3-methoxyphenyl)methyl]-1,3,8-triazaspiro[4.5]decan-2-one Chemical compound C[C@H](CN1CCC2(CC1)CN(C(=O)N2CC3=CC(=CC=C3)OC)C4=CC=C(C=C4)Br)O BYHQTRFJOGIQAO-GOSISDBHSA-N 0.000 description 1
- LENADRWBVLFBSX-UHFFFAOYSA-N 3-(4-methylpiperazin-1-yl)sulfonylaniline Chemical compound C1CN(C)CCN1S(=O)(=O)C1=CC=CC(N)=C1 LENADRWBVLFBSX-UHFFFAOYSA-N 0.000 description 1
- IHHKTIKNEDOMIK-UHFFFAOYSA-N 3-(morpholin-4-ylmethyl)aniline Chemical compound NC1=CC=CC(CN2CCOCC2)=C1 IHHKTIKNEDOMIK-UHFFFAOYSA-N 0.000 description 1
- AXORTWPDZUZSLG-UHFFFAOYSA-N 3-[(2-chloro-5-methylpyrimidin-4-yl)amino]-n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC(NC=2C(=CN=C(Cl)N=2)C)=C1 AXORTWPDZUZSLG-UHFFFAOYSA-N 0.000 description 1
- WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 1
- SRVXSISGYBMIHR-UHFFFAOYSA-N 3-[3-[3-(2-amino-2-oxoethyl)phenyl]-5-chlorophenyl]-3-(5-methyl-1,3-thiazol-2-yl)propanoic acid Chemical compound S1C(C)=CN=C1C(CC(O)=O)C1=CC(Cl)=CC(C=2C=C(CC(N)=O)C=CC=2)=C1 SRVXSISGYBMIHR-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
- SRWDQSRTOOMPMO-UHFFFAOYSA-N 3-bromo-1-benzothiophene Chemical compound C1=CC=C2C(Br)=CSC2=C1 SRWDQSRTOOMPMO-UHFFFAOYSA-N 0.000 description 1
- SHTGZBWYHRHZHT-UHFFFAOYSA-N 3-bromo-8-methylquinoline Chemical compound BrC1=CN=C2C(C)=CC=CC2=C1 SHTGZBWYHRHZHT-UHFFFAOYSA-N 0.000 description 1
- ZELYQSZTABGDLA-UHFFFAOYSA-N 3-bromo-n,n-diethylbenzenesulfonamide Chemical compound CCN(CC)S(=O)(=O)C1=CC=CC(Br)=C1 ZELYQSZTABGDLA-UHFFFAOYSA-N 0.000 description 1
- USEXQPWLCGBYNT-UHFFFAOYSA-N 3-bromo-n,n-dimethylaniline Chemical compound CN(C)C1=CC=CC(Br)=C1 USEXQPWLCGBYNT-UHFFFAOYSA-N 0.000 description 1
- RHBJVOGENJVLGT-UHFFFAOYSA-N 3-bromo-n,n-dimethylbenzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC=CC(Br)=C1 RHBJVOGENJVLGT-UHFFFAOYSA-N 0.000 description 1
- MLUYYAINRSPCFT-UHFFFAOYSA-N 3-bromo-n-cyclohexylbenzenesulfonamide Chemical compound BrC1=CC=CC(S(=O)(=O)NC2CCCCC2)=C1 MLUYYAINRSPCFT-UHFFFAOYSA-N 0.000 description 1
- UVSNSICXRVZAJR-UHFFFAOYSA-N 3-bromo-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(Br)=C1 UVSNSICXRVZAJR-UHFFFAOYSA-N 0.000 description 1
- YEZCGZSKQXNVDX-UHFFFAOYSA-N 3-bromo-n-propan-2-ylbenzenesulfonamide Chemical compound CC(C)NS(=O)(=O)C1=CC=CC(Br)=C1 YEZCGZSKQXNVDX-UHFFFAOYSA-N 0.000 description 1
- PJGOLCXVWIYXRQ-UHFFFAOYSA-N 3-bromobenzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC(Br)=C1 PJGOLCXVWIYXRQ-UHFFFAOYSA-N 0.000 description 1
- PBOOZQFGWNZNQE-UHFFFAOYSA-N 3-bromobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC(Br)=C1 PBOOZQFGWNZNQE-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- ZETIVVHRRQLWFW-UHFFFAOYSA-N 3-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC(C=O)=C1 ZETIVVHRRQLWFW-UHFFFAOYSA-N 0.000 description 1
- AHQOQYXOKZRRPJ-UHFFFAOYSA-N 3-piperidin-1-ylsulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)N2CCCCC2)=C1 AHQOQYXOKZRRPJ-UHFFFAOYSA-N 0.000 description 1
- AOJJSUZBOXZQNB-VTZDEGQISA-N 4'-epidoxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-VTZDEGQISA-N 0.000 description 1
- BLNPEJXSNSBBNM-UHFFFAOYSA-N 4-(1,2,4-triazol-1-yl)aniline Chemical compound C1=CC(N)=CC=C1N1N=CN=C1 BLNPEJXSNSBBNM-UHFFFAOYSA-N 0.000 description 1
- KTPONJJKCBOJCQ-UHFFFAOYSA-N 4-(2h-tetrazol-5-yl)aniline Chemical compound C1=CC(N)=CC=C1C1=NNN=N1 KTPONJJKCBOJCQ-UHFFFAOYSA-N 0.000 description 1
- LWJZRMBBOWCPMO-UHFFFAOYSA-N 4-(3-bromophenyl)piperidine Chemical compound BrC1=CC=CC(C2CCNCC2)=C1 LWJZRMBBOWCPMO-UHFFFAOYSA-N 0.000 description 1
- BMAMBBTZMVECJZ-UHFFFAOYSA-N 4-(3-bromophenyl)sulfonylmorpholine Chemical compound BrC1=CC=CC(S(=O)(=O)N2CCOCC2)=C1 BMAMBBTZMVECJZ-UHFFFAOYSA-N 0.000 description 1
- PJUPTRYCQKQLCI-UHFFFAOYSA-N 4-(4-methylimidazol-1-yl)aniline Chemical compound C1=NC(C)=CN1C1=CC=C(N)C=C1 PJUPTRYCQKQLCI-UHFFFAOYSA-N 0.000 description 1
- MOZNZNKHRXRLLF-UHFFFAOYSA-N 4-(4-methylpiperazin-1-yl)aniline Chemical compound C1CN(C)CCN1C1=CC=C(N)C=C1 MOZNZNKHRXRLLF-UHFFFAOYSA-N 0.000 description 1
- CDSJZBOLNDWPAA-UHFFFAOYSA-N 4-(4-nitrophenyl)piperidine Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1CCNCC1 CDSJZBOLNDWPAA-UHFFFAOYSA-N 0.000 description 1
- GXUQBVHIKVWWSN-UHFFFAOYSA-N 4-(5-aminopyridin-2-yl)piperazine-1-carboxylic acid Chemical compound N1=CC(N)=CC=C1N1CCN(C(O)=O)CC1 GXUQBVHIKVWWSN-UHFFFAOYSA-N 0.000 description 1
- DGHAOTHIDTUSJY-UHFFFAOYSA-N 4-(imidazol-1-ylmethyl)aniline Chemical compound C1=CC(N)=CC=C1CN1C=NC=C1 DGHAOTHIDTUSJY-UHFFFAOYSA-N 0.000 description 1
- WZXYYQHVDJMIFF-UHFFFAOYSA-N 4-(pyridin-4-ylmethyl)aniline Chemical compound C1=CC(N)=CC=C1CC1=CC=NC=C1 WZXYYQHVDJMIFF-UHFFFAOYSA-N 0.000 description 1
- KWSBIEFIWQOXTF-UHFFFAOYSA-N 4-[(2-methylimidazol-1-yl)methyl]aniline Chemical compound CC1=NC=CN1CC1=CC=C(N)C=C1 KWSBIEFIWQOXTF-UHFFFAOYSA-N 0.000 description 1
- HURUBYXXNGTARE-UHFFFAOYSA-N 4-[(4-chloropyrimidin-2-yl)amino]-n-(2-pyrrolidin-1-ylethyl)benzenesulfonamide Chemical compound ClC1=CC=NC(NC=2C=CC(=CC=2)S(=O)(=O)NCCN2CCCC2)=N1 HURUBYXXNGTARE-UHFFFAOYSA-N 0.000 description 1
- YFCIFWOJYYFDQP-PTWZRHHISA-N 4-[3-amino-6-[(1S,3S,4S)-3-fluoro-4-hydroxycyclohexyl]pyrazin-2-yl]-N-[(1S)-1-(3-bromo-5-fluorophenyl)-2-(methylamino)ethyl]-2-fluorobenzamide Chemical compound CNC[C@@H](NC(=O)c1ccc(cc1F)-c1nc(cnc1N)[C@H]1CC[C@H](O)[C@@H](F)C1)c1cc(F)cc(Br)c1 YFCIFWOJYYFDQP-PTWZRHHISA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- OUYKLBUUWLGYAF-UHFFFAOYSA-N 4-[[4-(3-hydroxyanilino)pyrimidin-2-yl]amino]-n-(2-pyrrolidin-1-ylethyl)benzenesulfonamide Chemical compound OC1=CC=CC(NC=2N=C(NC=3C=CC(=CC=3)S(=O)(=O)NCCN3CCCC3)N=CC=2)=C1 OUYKLBUUWLGYAF-UHFFFAOYSA-N 0.000 description 1
- JEVUEEJDBYYNLQ-UHFFFAOYSA-N 4-[[4-(3-methoxyanilino)pyrimidin-2-yl]amino]-n-(2-pyrrolidin-1-ylethyl)benzenesulfonamide Chemical compound COC1=CC=CC(NC=2N=C(NC=3C=CC(=CC=3)S(=O)(=O)NCCN3CCCC3)N=CC=2)=C1 JEVUEEJDBYYNLQ-UHFFFAOYSA-N 0.000 description 1
- HNRHHOMURSWDOP-UHFFFAOYSA-N 4-[[4-(4-hydroxyanilino)pyrimidin-2-yl]amino]-n-(2-pyrrolidin-1-ylethyl)benzenesulfonamide Chemical compound C1=CC(O)=CC=C1NC1=CC=NC(NC=2C=CC(=CC=2)S(=O)(=O)NCCN2CCCC2)=N1 HNRHHOMURSWDOP-UHFFFAOYSA-N 0.000 description 1
- RGURATFXZKMFHA-UHFFFAOYSA-N 4-[[4-(4-methoxyanilino)pyrimidin-2-yl]amino]-n-(2-pyrrolidin-1-ylethyl)benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1NC1=CC=NC(NC=2C=CC(=CC=2)S(=O)(=O)NCCN2CCCC2)=N1 RGURATFXZKMFHA-UHFFFAOYSA-N 0.000 description 1
- OZCOWQYDGHSSFS-UHFFFAOYSA-N 4-amino-2-[3-(2-pyrrolidin-1-ylethoxy)anilino]pyrimidine-5-carbonitrile Chemical compound C1=C(C#N)C(N)=NC(NC=2C=C(OCCN3CCCC3)C=CC=2)=N1 OZCOWQYDGHSSFS-UHFFFAOYSA-N 0.000 description 1
- XDVWKQPVZMFZBU-UHFFFAOYSA-N 4-amino-2-[4-(2-pyrrolidin-1-ylethoxy)anilino]pyrimidine-5-carbonitrile Chemical compound C1=C(C#N)C(N)=NC(NC=2C=CC(OCCN3CCCC3)=CC=2)=N1 XDVWKQPVZMFZBU-UHFFFAOYSA-N 0.000 description 1
- KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
- RWGQDQJALINEME-UHFFFAOYSA-N 4-benzyl-2-chloropyrimidine Chemical compound ClC1=NC=CC(CC=2C=CC=CC=2)=N1 RWGQDQJALINEME-UHFFFAOYSA-N 0.000 description 1
- CFPZDVAZISWERM-UHFFFAOYSA-N 4-bromo-1,2-dichlorobenzene Chemical compound ClC1=CC=C(Br)C=C1Cl CFPZDVAZISWERM-UHFFFAOYSA-N 0.000 description 1
- VZPMQHSDFWAZHP-UHFFFAOYSA-N 4-bromo-1,3-benzodioxole Chemical compound BrC1=CC=CC2=C1OCO2 VZPMQHSDFWAZHP-UHFFFAOYSA-N 0.000 description 1
- XGOCKBMEZPNDPJ-UHFFFAOYSA-N 4-bromo-1-chloro-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC(Br)=CC=C1Cl XGOCKBMEZPNDPJ-UHFFFAOYSA-N 0.000 description 1
- AGYWDGVTLKNTBS-UHFFFAOYSA-N 4-bromo-1-chloro-2-fluorobenzene Chemical compound FC1=CC(Br)=CC=C1Cl AGYWDGVTLKNTBS-UHFFFAOYSA-N 0.000 description 1
- OZFQMHJKAODEON-UHFFFAOYSA-N 4-bromo-1-chloro-2-methylbenzene Chemical compound CC1=CC(Br)=CC=C1Cl OZFQMHJKAODEON-UHFFFAOYSA-N 0.000 description 1
- SRYXZVWRMOFVCO-UHFFFAOYSA-N 4-bromo-1-methyl-2-methylsulfonylbenzene Chemical compound CC1=CC=C(Br)C=C1S(C)(=O)=O SRYXZVWRMOFVCO-UHFFFAOYSA-N 0.000 description 1
- KJIODOACRIRBPB-UHFFFAOYSA-N 4-bromo-1h-indazole Chemical compound BrC1=CC=CC2=C1C=NN2 KJIODOACRIRBPB-UHFFFAOYSA-N 0.000 description 1
- AYQBMZNSJPVADT-UHFFFAOYSA-N 4-bromo-2-chlorobenzonitrile Chemical compound ClC1=CC(Br)=CC=C1C#N AYQBMZNSJPVADT-UHFFFAOYSA-N 0.000 description 1
- PBQKMEMSAFAVKF-UHFFFAOYSA-N 4-bromo-7-fluoro-1h-indole Chemical compound FC1=CC=C(Br)C2=C1NC=C2 PBQKMEMSAFAVKF-UHFFFAOYSA-N 0.000 description 1
- DIYRIYJMMLUTQP-UHFFFAOYSA-N 4-bromo-n-(2-pyrrolidin-1-ylethyl)benzenesulfonamide Chemical compound C1=CC(Br)=CC=C1S(=O)(=O)NCCN1CCCC1 DIYRIYJMMLUTQP-UHFFFAOYSA-N 0.000 description 1
- KMMHZIBWCXYAAH-UHFFFAOYSA-N 4-bromobenzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=C(Br)C=C1 KMMHZIBWCXYAAH-UHFFFAOYSA-N 0.000 description 1
- DBGFGNCFYUNXLD-UHFFFAOYSA-N 4-chloropyrimidin-2-amine Chemical compound NC1=NC=CC(Cl)=N1 DBGFGNCFYUNXLD-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- XXVCIDLHARIYBR-UHFFFAOYSA-N 4-n-(1,3-benzodioxol-4-yl)-2-n-[3-methoxy-4-(2-pyrrolidin-1-ylethoxy)phenyl]-5-methylpyrimidine-2,4-diamine Chemical compound COC1=CC(NC=2N=C(NC=3C=4OCOC=4C=CC=3)C(C)=CN=2)=CC=C1OCCN1CCCC1 XXVCIDLHARIYBR-UHFFFAOYSA-N 0.000 description 1
- XKFYKNIIDRJCTF-UHFFFAOYSA-N 4-n-(1-benzothiophen-3-yl)-5-methyl-2-n-[4-(2-pyrrolidin-1-ylethoxy)phenyl]pyrimidine-2,4-diamine Chemical compound N1=C(NC=2C3=CC=CC=C3SC=2)C(C)=CN=C1NC(C=C1)=CC=C1OCCN1CCCC1 XKFYKNIIDRJCTF-UHFFFAOYSA-N 0.000 description 1
- WZLMHINNKXSGOD-UHFFFAOYSA-N 4-n-(1-benzothiophen-5-yl)-5-methyl-2-n-[4-(2-pyrrolidin-1-ylethoxy)phenyl]pyrimidine-2,4-diamine Chemical compound N1=C(NC=2C=C3C=CSC3=CC=2)C(C)=CN=C1NC(C=C1)=CC=C1OCCN1CCCC1 WZLMHINNKXSGOD-UHFFFAOYSA-N 0.000 description 1
- VCRQSXBDRXJWJB-UHFFFAOYSA-N 4-n-(3-chlorophenyl)-5-methyl-2-n-[4-(2-pyrrolidin-1-ylethoxy)phenyl]pyrimidine-2,4-diamine Chemical compound N1=C(NC=2C=C(Cl)C=CC=2)C(C)=CN=C1NC(C=C1)=CC=C1OCCN1CCCC1 VCRQSXBDRXJWJB-UHFFFAOYSA-N 0.000 description 1
- MMEISHYONRFFBS-UHFFFAOYSA-N 4-n-(4-chloro-3-methoxyphenyl)-4-n,5-dimethyl-2-n-[4-(2-pyrrolidin-1-ylethoxy)phenyl]pyrimidine-2,4-diamine Chemical compound C1=C(Cl)C(OC)=CC(N(C)C=2C(=CN=C(NC=3C=CC(OCCN4CCCC4)=CC=3)N=2)C)=C1 MMEISHYONRFFBS-UHFFFAOYSA-N 0.000 description 1
- PUZXAMNAUOMURN-UHFFFAOYSA-N 4-n-(4-chloro-3-methoxyphenyl)-5-methyl-2-n-[4-(morpholin-4-ylmethyl)phenyl]pyrimidine-2,4-diamine Chemical compound C1=C(Cl)C(OC)=CC(NC=2C(=CN=C(NC=3C=CC(CN4CCOCC4)=CC=3)N=2)C)=C1 PUZXAMNAUOMURN-UHFFFAOYSA-N 0.000 description 1
- YQNKMHCDYFPFDQ-UHFFFAOYSA-N 4-n-(7-chloro-1h-indol-4-yl)-5-methyl-2-n-[4-(4-methylpiperazin-1-yl)phenyl]pyrimidine-2,4-diamine Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C)C(NC=2C=3C=CNC=3C(Cl)=CC=2)=N1 YQNKMHCDYFPFDQ-UHFFFAOYSA-N 0.000 description 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
- LLBZPESJRQGYMB-UHFFFAOYSA-N 4-one Natural products O1C(C(=O)CC)CC(C)C11C2(C)CCC(C3(C)C(C(C)(CO)C(OC4C(C(O)C(O)C(COC5C(C(O)C(O)CO5)OC5C(C(OC6C(C(O)C(O)C(CO)O6)O)C(O)C(CO)O5)OC5C(C(O)C(O)C(C)O5)O)O4)O)CC3)CC3)=C3C2(C)CC1 LLBZPESJRQGYMB-UHFFFAOYSA-N 0.000 description 1
- MIUOBAHGBPSRKY-UHFFFAOYSA-N 5-(4-nitrophenyl)-2h-tetrazole Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=NNN=N1 MIUOBAHGBPSRKY-UHFFFAOYSA-N 0.000 description 1
- IRPVABHDSJVBNZ-RTHVDDQRSA-N 5-[1-(cyclopropylmethyl)-5-[(1R,5S)-3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-6-yl]pyrazol-3-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C1=NN(CC2CC2)C(C2[C@@H]3CN(C[C@@H]32)C2COC2)=C1 IRPVABHDSJVBNZ-RTHVDDQRSA-N 0.000 description 1
- FBOYMIDCHINJKC-UHFFFAOYSA-N 5-bromo-1,3-benzodioxole Chemical compound BrC1=CC=C2OCOC2=C1 FBOYMIDCHINJKC-UHFFFAOYSA-N 0.000 description 1
- RDSIMGKJEYNNLF-UHFFFAOYSA-N 5-bromo-1-benzothiophene Chemical compound BrC1=CC=C2SC=CC2=C1 RDSIMGKJEYNNLF-UHFFFAOYSA-N 0.000 description 1
- PKTXUGAXFJNLQR-UHFFFAOYSA-N 5-bromo-2-chloro-1,3-dimethylbenzene Chemical compound CC1=CC(Br)=CC(C)=C1Cl PKTXUGAXFJNLQR-UHFFFAOYSA-N 0.000 description 1
- AHUXEFWSXHFQIP-UHFFFAOYSA-N 5-bromo-n-tert-butyl-2-methylbenzenesulfonamide Chemical compound CC1=CC=C(Br)C=C1S(=O)(=O)NC(C)(C)C AHUXEFWSXHFQIP-UHFFFAOYSA-N 0.000 description 1
- VXXVJGLTTFDMOW-UHFFFAOYSA-N 5-methyl-2-n-[3-(4-methylpiperazin-1-yl)sulfonylphenyl]pyrimidine-2,4-diamine Chemical compound C1CN(C)CCN1S(=O)(=O)C1=CC=CC(NC=2N=C(N)C(C)=CN=2)=C1 VXXVJGLTTFDMOW-UHFFFAOYSA-N 0.000 description 1
- ITXGCDCDTFITIT-UHFFFAOYSA-N 5-methyl-2-n-[3-(morpholin-4-ylmethyl)phenyl]pyrimidine-2,4-diamine Chemical compound N1=C(N)C(C)=CN=C1NC1=CC=CC(CN2CCOCC2)=C1 ITXGCDCDTFITIT-UHFFFAOYSA-N 0.000 description 1
- ZZJKEYQBIXNXBL-UHFFFAOYSA-N 5-methyl-2-n-[4-(4-methylpiperazin-1-yl)phenyl]-4-n-(3-morpholin-4-ylsulfonylphenyl)pyrimidine-2,4-diamine Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C)C(NC=2C=C(C=CC=2)S(=O)(=O)N2CCOCC2)=N1 ZZJKEYQBIXNXBL-UHFFFAOYSA-N 0.000 description 1
- MQLVUECINJOYDI-UHFFFAOYSA-N 5-methyl-2-n-[4-(4-methylpiperazin-1-yl)phenyl]-4-n-(3-pyrrol-1-ylphenyl)pyrimidine-2,4-diamine Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C)C(NC=2C=C(C=CC=2)N2C=CC=C2)=N1 MQLVUECINJOYDI-UHFFFAOYSA-N 0.000 description 1
- HZYKTMNELNYUID-UHFFFAOYSA-N 5-methyl-2-n-[4-(4-methylpiperazin-1-yl)phenyl]-4-n-(3-pyrrolidin-1-ylsulfonylphenyl)pyrimidine-2,4-diamine Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C)C(NC=2C=C(C=CC=2)S(=O)(=O)N2CCCC2)=N1 HZYKTMNELNYUID-UHFFFAOYSA-N 0.000 description 1
- JZHAICAGPHJUQY-UHFFFAOYSA-N 5-methyl-2-n-[4-(4-methylpiperazin-1-yl)phenyl]pyrimidine-2,4-diamine Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C)C(N)=N1 JZHAICAGPHJUQY-UHFFFAOYSA-N 0.000 description 1
- UMTGKMJCXHCZBB-UHFFFAOYSA-N 5-methyl-2-n-[4-(morpholin-4-ylmethyl)phenyl]pyrimidine-2,4-diamine Chemical compound N1=C(N)C(C)=CN=C1NC(C=C1)=CC=C1CN1CCOCC1 UMTGKMJCXHCZBB-UHFFFAOYSA-N 0.000 description 1
- OGCGJIBOJMPSSS-UHFFFAOYSA-N 5-methyl-4-n-(7-methyl-1h-indol-4-yl)-2-n-[4-(2-pyrrolidin-1-ylethoxy)phenyl]pyrimidine-2,4-diamine Chemical compound N1=C(NC=2C=3C=CNC=3C(C)=CC=2)C(C)=CN=C1NC(C=C1)=CC=C1OCCN1CCCC1 OGCGJIBOJMPSSS-UHFFFAOYSA-N 0.000 description 1
- ZWWUSMFXWBBOCM-UHFFFAOYSA-N 5-methyl-4-n-(7-methyl-1h-indol-4-yl)-2-n-[4-(4-methylpiperazin-1-yl)phenyl]pyrimidine-2,4-diamine Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C)C(NC=2C=3C=CNC=3C(C)=CC=2)=N1 ZWWUSMFXWBBOCM-UHFFFAOYSA-N 0.000 description 1
- KCBWAFJCKVKYHO-UHFFFAOYSA-N 6-(4-cyclopropyl-6-methoxypyrimidin-5-yl)-1-[[4-[1-propan-2-yl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]pyrazolo[3,4-d]pyrimidine Chemical compound C1(CC1)C1=NC=NC(=C1C1=NC=C2C(=N1)N(N=C2)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C(C)C)OC KCBWAFJCKVKYHO-UHFFFAOYSA-N 0.000 description 1
- CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 208000031261 Acute myeloid leukaemia Diseases 0.000 description 1
- 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 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 241000271566 Aves Species 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 108010006654 Bleomycin Proteins 0.000 description 1
- 201000004569 Blindness Diseases 0.000 description 1
- 208000020084 Bone disease Diseases 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- 241000219193 Brassicaceae Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 description 1
- 241000282465 Canis Species 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 108010012236 Chemokines Proteins 0.000 description 1
- 102000019034 Chemokines Human genes 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 108010005939 Ciliary Neurotrophic Factor Proteins 0.000 description 1
- 102100031614 Ciliary neurotrophic factor Human genes 0.000 description 1
- 108010071942 Colony-Stimulating Factors Proteins 0.000 description 1
- 102000007644 Colony-Stimulating Factors Human genes 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- 229930105110 Cyclosporin A Natural products 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
- 108010036941 Cyclosporins Proteins 0.000 description 1
- 102000003915 DNA Topoisomerases Human genes 0.000 description 1
- 108090000323 DNA Topoisomerases Proteins 0.000 description 1
- 230000000970 DNA cross-linking effect Effects 0.000 description 1
- 229940123780 DNA topoisomerase I inhibitor Drugs 0.000 description 1
- WEAHRLBPCANXCN-UHFFFAOYSA-N Daunomycin Natural products CCC1(O)CC(OC2CC(N)C(O)C(C)O2)c3cc4C(=O)c5c(OC)cccc5C(=O)c4c(O)c3C1 WEAHRLBPCANXCN-UHFFFAOYSA-N 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- 208000002249 Diabetes Complications Diseases 0.000 description 1
- 206010059866 Drug resistance Diseases 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- 206010049119 Emotional distress Diseases 0.000 description 1
- 102000009024 Epidermal Growth Factor Human genes 0.000 description 1
- 102400001368 Epidermal growth factor Human genes 0.000 description 1
- 101800003838 Epidermal growth factor Proteins 0.000 description 1
- HTIJFSOGRVMCQR-UHFFFAOYSA-N Epirubicin Natural products COc1cccc2C(=O)c3c(O)c4CC(O)(CC(OC5CC(N)C(=O)C(C)O5)c4c(O)c3C(=O)c12)C(=O)CO HTIJFSOGRVMCQR-UHFFFAOYSA-N 0.000 description 1
- 102100036509 Erythropoietin receptor Human genes 0.000 description 1
- 101710102442 Erythropoietin receptor Proteins 0.000 description 1
- GISRWBROCYNDME-PELMWDNLSA-N F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C Chemical compound F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C GISRWBROCYNDME-PELMWDNLSA-N 0.000 description 1
- 241000282324 Felis Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 1
- 102000003688 G-Protein-Coupled Receptors Human genes 0.000 description 1
- 108090000045 G-Protein-Coupled Receptors Proteins 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 206010017993 Gastrointestinal neoplasms Diseases 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- 102000009465 Growth Factor Receptors Human genes 0.000 description 1
- 108010009202 Growth Factor Receptors Proteins 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 239000012981 Hank's balanced salt solution Substances 0.000 description 1
- 208000035186 Hemolytic Autoimmune Anemia Diseases 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 101000602164 Homo sapiens Platelet-derived growth factor subunit A Proteins 0.000 description 1
- 101001012157 Homo sapiens Receptor tyrosine-protein kinase erbB-2 Proteins 0.000 description 1
- 101001059454 Homo sapiens Serine/threonine-protein kinase MARK2 Proteins 0.000 description 1
- 101000845170 Homo sapiens Thymic stromal lymphopoietin Proteins 0.000 description 1
- 101000934996 Homo sapiens Tyrosine-protein kinase JAK3 Proteins 0.000 description 1
- 101000610640 Homo sapiens U4/U6 small nuclear ribonucleoprotein Prp3 Proteins 0.000 description 1
- 241000701806 Human papillomavirus Species 0.000 description 1
- 108091069211 IL-3 family Proteins 0.000 description 1
- 102000039992 IL-3 family Human genes 0.000 description 1
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 1
- 206010062016 Immunosuppression Diseases 0.000 description 1
- 108010064600 Intercellular Adhesion Molecule-3 Proteins 0.000 description 1
- 102100037871 Intercellular adhesion molecule 3 Human genes 0.000 description 1
- 102100037850 Interferon gamma Human genes 0.000 description 1
- 102000006992 Interferon-alpha Human genes 0.000 description 1
- 108010047761 Interferon-alpha Proteins 0.000 description 1
- 108010074328 Interferon-gamma Proteins 0.000 description 1
- 102000003814 Interleukin-10 Human genes 0.000 description 1
- 108090000174 Interleukin-10 Proteins 0.000 description 1
- 102000003815 Interleukin-11 Human genes 0.000 description 1
- 108090000177 Interleukin-11 Proteins 0.000 description 1
- 108090000176 Interleukin-13 Proteins 0.000 description 1
- 108090000172 Interleukin-15 Proteins 0.000 description 1
- 102100039879 Interleukin-19 Human genes 0.000 description 1
- 108050009288 Interleukin-19 Proteins 0.000 description 1
- 108010002586 Interleukin-7 Proteins 0.000 description 1
- 108010002335 Interleukin-9 Proteins 0.000 description 1
- 101150009057 JAK2 gene Proteins 0.000 description 1
- 101150069380 JAK3 gene Proteins 0.000 description 1
- 206010072206 Janus kinase 2 mutation Diseases 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 1
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 102100032352 Leukemia inhibitory factor Human genes 0.000 description 1
- 108090000581 Leukemia inhibitory factor Proteins 0.000 description 1
- 102000008072 Lymphokines Human genes 0.000 description 1
- 108010074338 Lymphokines Proteins 0.000 description 1
- 108010046938 Macrophage Colony-Stimulating Factor Proteins 0.000 description 1
- 102100028123 Macrophage colony-stimulating factor 1 Human genes 0.000 description 1
- 206010027480 Metastatic malignant melanoma Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 102000029749 Microtubule Human genes 0.000 description 1
- 108091022875 Microtubule Proteins 0.000 description 1
- PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 description 1
- 102000013967 Monokines Human genes 0.000 description 1
- 108010050619 Monokines Proteins 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 201000003793 Myelodysplastic syndrome Diseases 0.000 description 1
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 1
- 241001274216 Naso Species 0.000 description 1
- 208000012902 Nervous system disease Diseases 0.000 description 1
- 208000025966 Neurological disease Diseases 0.000 description 1
- IDRGFNPZDVBSSE-UHFFFAOYSA-N OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F Chemical compound OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F IDRGFNPZDVBSSE-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 108090000630 Oncostatin M Proteins 0.000 description 1
- 102100031942 Oncostatin-M Human genes 0.000 description 1
- 102000004316 Oxidoreductases Human genes 0.000 description 1
- 108090000854 Oxidoreductases Proteins 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241001631646 Papillomaviridae Species 0.000 description 1
- 208000032721 Philadelphia Chromosome Diseases 0.000 description 1
- 102100037596 Platelet-derived growth factor subunit A Human genes 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 208000008601 Polycythemia Diseases 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 241000288906 Primates Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 102100030086 Receptor tyrosine-protein kinase erbB-2 Human genes 0.000 description 1
- 208000007135 Retinal Neovascularization Diseases 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- RYMZZMVNJRMUDD-UHFFFAOYSA-N SJ000286063 Natural products C12C(OC(=O)C(C)(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 RYMZZMVNJRMUDD-UHFFFAOYSA-N 0.000 description 1
- 101001110823 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) 60S ribosomal protein L6-A Proteins 0.000 description 1
- 101000712176 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) 60S ribosomal protein L6-B Proteins 0.000 description 1
- 101000650578 Salmonella phage P22 Regulatory protein C3 Proteins 0.000 description 1
- 102100028904 Serine/threonine-protein kinase MARK2 Human genes 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229940123237 Taxane Drugs 0.000 description 1
- FOCVUCIESVLUNU-UHFFFAOYSA-N Thiotepa Chemical compound C1CN1P(N1CC1)(=S)N1CC1 FOCVUCIESVLUNU-UHFFFAOYSA-N 0.000 description 1
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 1
- 239000004473 Threonine Substances 0.000 description 1
- 102100031294 Thymic stromal lymphopoietin Human genes 0.000 description 1
- 239000000365 Topoisomerase I Inhibitor Substances 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 101001040920 Triticum aestivum Alpha-amylase inhibitor 0.28 Proteins 0.000 description 1
- 108060008683 Tumor Necrosis Factor Receptor Proteins 0.000 description 1
- 102100025387 Tyrosine-protein kinase JAK3 Human genes 0.000 description 1
- 102100040374 U4/U6 small nuclear ribonucleoprotein Prp3 Human genes 0.000 description 1
- 108010073929 Vascular Endothelial Growth Factor A Proteins 0.000 description 1
- LXRZVMYMQHNYJB-UNXOBOICSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 LXRZVMYMQHNYJB-UNXOBOICSA-N 0.000 description 1
- WERKSKAQRVDLDW-ANOHMWSOSA-N [(2s,3r,4r,5r)-2,3,4,5,6-pentahydroxyhexyl] (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO WERKSKAQRVDLDW-ANOHMWSOSA-N 0.000 description 1
- MBHRHUJRKGNOKX-UHFFFAOYSA-N [(4,6-diamino-1,3,5-triazin-2-yl)amino]methanol Chemical compound NC1=NC(N)=NC(NCO)=N1 MBHRHUJRKGNOKX-UHFFFAOYSA-N 0.000 description 1
- PCSBRUOROMKFCU-UQJCYSKFSA-N [2-[(2S,4S)-4-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1H-tetracen-2-yl]-2-oxoethyl] benzoate 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)COC(=O)C=1C=CC=CC=1)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 PCSBRUOROMKFCU-UQJCYSKFSA-N 0.000 description 1
- MFUJRSZQSMPGLX-UHFFFAOYSA-N [2-[4-(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1h-tetracen-2-yl]-2-oxoethyl] octanoate Chemical compound C12=C(O)C=3C(=O)C4=C(OC)C=CC=C4C(=O)C=3C(O)=C2CC(C(=O)COC(=O)CCCCCCC)(O)CC1OC1CC(N)C(O)C(C)O1 MFUJRSZQSMPGLX-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 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
- 229960004150 aciclovir Drugs 0.000 description 1
- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 229940064305 adrucil Drugs 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229960002932 anastrozole Drugs 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- RGHILYZRVFRRNK-UHFFFAOYSA-N anthracene-1,2-dione Chemical class C1=CC=C2C=C(C(C(=O)C=C3)=O)C3=CC2=C1 RGHILYZRVFRRNK-UHFFFAOYSA-N 0.000 description 1
- 239000003817 anthracycline antibiotic agent Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940046836 anti-estrogen Drugs 0.000 description 1
- 230000001833 anti-estrogenic effect Effects 0.000 description 1
- 230000002942 anti-growth Effects 0.000 description 1
- 230000001028 anti-proliverative effect Effects 0.000 description 1
- 230000000692 anti-sense effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 229940125715 antihistaminic agent Drugs 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 229940045719 antineoplastic alkylating agent nitrosoureas Drugs 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 229940045985 antineoplastic platinum compound Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 230000006907 apoptotic process Effects 0.000 description 1
- 239000012223 aqueous fraction Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229940078010 arimidex Drugs 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960003272 asparaginase Drugs 0.000 description 1
- DCXYFEDJOCDNAF-UHFFFAOYSA-M asparaginate Chemical compound [O-]C(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-M 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 201000000448 autoimmune hemolytic anemia Diseases 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000008436 biogenesis Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000008827 biological function Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical class N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C OYVAGSVQBOHSSS-UAPAGMARSA-O 0.000 description 1
- 210000001185 bone marrow Anatomy 0.000 description 1
- 239000007975 buffered saline Substances 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 229960002092 busulfan Drugs 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229940127093 camptothecin Drugs 0.000 description 1
- VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical compound C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 229920003123 carboxymethyl cellulose sodium Polymers 0.000 description 1
- 229940063834 carboxymethylcellulose sodium Drugs 0.000 description 1
- XREUEWVEMYWFFA-CSKJXFQVSA-N carminomycin Chemical compound C1[C@H](N)[C@H](O)[C@H](C)O[C@H]1O[C@@H]1C2=C(O)C(C(=O)C3=C(O)C=CC=C3C3=O)=C3C(O)=C2C[C@@](O)(C(C)=O)C1 XREUEWVEMYWFFA-CSKJXFQVSA-N 0.000 description 1
- 229930188550 carminomycin Natural products 0.000 description 1
- XREUEWVEMYWFFA-UHFFFAOYSA-N carminomycin I Natural products C1C(N)C(O)C(C)OC1OC1C2=C(O)C(C(=O)C3=C(O)C=CC=C3C3=O)=C3C(O)=C2CC(O)(C(C)=O)C1 XREUEWVEMYWFFA-UHFFFAOYSA-N 0.000 description 1
- 229950001725 carubicin Drugs 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 230000022131 cell cycle Effects 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 230000007248 cellular mechanism Effects 0.000 description 1
- 230000036755 cellular response Effects 0.000 description 1
- 230000005754 cellular signaling Effects 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 150000005829 chemical entities Chemical class 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 235000013330 chicken meat Nutrition 0.000 description 1
- JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 description 1
- 229960004630 chlorambucil Drugs 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 210000000349 chromosome Anatomy 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 229960001265 ciclosporin Drugs 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 229960001338 colchicine Drugs 0.000 description 1
- 229940047120 colony stimulating factors Drugs 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000002648 combination therapy Methods 0.000 description 1
- 230000001010 compromised effect Effects 0.000 description 1
- 230000006552 constitutive activation Effects 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
- 229940097362 cyclodextrins Drugs 0.000 description 1
- 229930182912 cyclosporin Natural products 0.000 description 1
- 229940104302 cytosine Drugs 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 229960003901 dacarbazine Drugs 0.000 description 1
- 229960000975 daunorubicin Drugs 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- KXGVEGMKQFWNSR-LLQZFEROSA-N deoxycholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 KXGVEGMKQFWNSR-LLQZFEROSA-N 0.000 description 1
- 229960003964 deoxycholic acid Drugs 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 230000002074 deregulated effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 229960003957 dexamethasone Drugs 0.000 description 1
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 1
- WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 208000024558 digestive system cancer Diseases 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- 230000009429 distress Effects 0.000 description 1
- ODCCJTMPMUFERV-UHFFFAOYSA-N ditert-butyl carbonate Chemical compound CC(C)(C)OC(=O)OC(C)(C)C ODCCJTMPMUFERV-UHFFFAOYSA-N 0.000 description 1
- VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 description 1
- 239000003534 dna topoisomerase inhibitor Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 239000000890 drug combination Substances 0.000 description 1
- 239000012636 effector Substances 0.000 description 1
- 239000003974 emollient agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 229940116977 epidermal growth factor Drugs 0.000 description 1
- 229960001904 epirubicin Drugs 0.000 description 1
- AAKJLRGGTJKAMG-UHFFFAOYSA-N erlotinib Chemical compound C=12C=C(OCCOC)C(OCCOC)=CC2=NC=NC=1NC1=CC=CC(C#C)=C1 AAKJLRGGTJKAMG-UHFFFAOYSA-N 0.000 description 1
- 229960001433 erlotinib Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000328 estrogen antagonist Substances 0.000 description 1
- KABVJIWNNHXRTJ-UHFFFAOYSA-N ethyl 2-methyl-3-[[5-methyl-2-[4-(4-methylpiperazin-1-yl)anilino]pyrimidin-4-yl]amino]benzoate Chemical compound CCOC(=O)C1=CC=CC(NC=2C(=CN=C(NC=3C=CC(=CC=3)N3CCN(C)CC3)N=2)C)=C1C KABVJIWNNHXRTJ-UHFFFAOYSA-N 0.000 description 1
- QYOBDWUUYSHDLY-UHFFFAOYSA-N ethyl 3-[[5-methyl-2-[4-(4-methylpiperazin-1-yl)anilino]pyrimidin-4-yl]amino]benzoate Chemical compound CCOC(=O)C1=CC=CC(NC=2C(=CN=C(NC=3C=CC(=CC=3)N3CCN(C)CC3)N=2)C)=C1 QYOBDWUUYSHDLY-UHFFFAOYSA-N 0.000 description 1
- ISZDEZLLBGJTTF-UHFFFAOYSA-N ethyl 3-bromo-2-methylbenzoate Chemical compound CCOC(=O)C1=CC=CC(Br)=C1C ISZDEZLLBGJTTF-UHFFFAOYSA-N 0.000 description 1
- QAUASTLEZAPQTB-UHFFFAOYSA-N ethyl 3-bromobenzoate Chemical compound CCOC(=O)C1=CC=CC(Br)=C1 QAUASTLEZAPQTB-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 239000004403 ethyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010228 ethyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229940043351 ethyl-p-hydroxybenzoate Drugs 0.000 description 1
- NUVBSKCKDOMJSU-UHFFFAOYSA-N ethylparaben Chemical compound CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 description 1
- 229960005420 etoposide Drugs 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 239000010685 fatty oil Substances 0.000 description 1
- 229960000390 fludarabine Drugs 0.000 description 1
- GIUYCYHIANZCFB-FJFJXFQQSA-N fludarabine phosphate Chemical compound C1=NC=2C(N)=NC(F)=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O GIUYCYHIANZCFB-FJFJXFQQSA-N 0.000 description 1
- 150000005699 fluoropyrimidines Chemical class 0.000 description 1
- 229960002949 fluorouracil Drugs 0.000 description 1
- 229960002074 flutamide Drugs 0.000 description 1
- MKXKFYHWDHIYRV-UHFFFAOYSA-N flutamide Chemical compound CC(C)C(=O)NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 MKXKFYHWDHIYRV-UHFFFAOYSA-N 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 238000002825 functional assay Methods 0.000 description 1
- 108020001507 fusion proteins Proteins 0.000 description 1
- 102000037865 fusion proteins Human genes 0.000 description 1
- IRSCQMHQWWYFCW-UHFFFAOYSA-N ganciclovir Chemical compound O=C1NC(N)=NC2=C1N=CN2COC(CO)CO IRSCQMHQWWYFCW-UHFFFAOYSA-N 0.000 description 1
- 229960002963 ganciclovir Drugs 0.000 description 1
- 201000010231 gastrointestinal system cancer Diseases 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 238000001415 gene therapy Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000003862 glucocorticoid Substances 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- 229940074045 glyceryl distearate Drugs 0.000 description 1
- 229940075507 glyceryl monostearate Drugs 0.000 description 1
- 150000002344 gold compounds Chemical class 0.000 description 1
- 210000003714 granulocyte Anatomy 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 230000003394 haemopoietic effect Effects 0.000 description 1
- 239000007902 hard capsule Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 201000011066 hemangioma Diseases 0.000 description 1
- FBPFZTCFMRRESA-UHFFFAOYSA-N hexane-1,2,3,4,5,6-hexol Chemical compound OCC(O)C(O)C(O)C(O)CO FBPFZTCFMRRESA-UHFFFAOYSA-N 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 230000003284 homeostatic effect Effects 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 229960001680 ibuprofen Drugs 0.000 description 1
- 229940099279 idamycin Drugs 0.000 description 1
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
- 239000000367 immunologic factor Substances 0.000 description 1
- 239000002955 immunomodulating agent Substances 0.000 description 1
- 229940121354 immunomodulator Drugs 0.000 description 1
- 230000002584 immunomodulator Effects 0.000 description 1
- 230000001506 immunosuppresive effect Effects 0.000 description 1
- 238000009169 immunotherapy Methods 0.000 description 1
- 231100000110 immunotoxic Toxicity 0.000 description 1
- 230000002625 immunotoxic effect Effects 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 229940102213 injectable suspension Drugs 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 102000006495 integrins Human genes 0.000 description 1
- 108010044426 integrins Proteins 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 108090000681 interleukin 20 Proteins 0.000 description 1
- 102000004114 interleukin 20 Human genes 0.000 description 1
- 108010074108 interleukin-21 Proteins 0.000 description 1
- 108010074109 interleukin-22 Proteins 0.000 description 1
- UEXQBEVWFZKHNB-UHFFFAOYSA-N intermediate 29 Natural products C1=CC(N)=CC=C1NC1=NC=CC=N1 UEXQBEVWFZKHNB-UHFFFAOYSA-N 0.000 description 1
- 230000004068 intracellular signaling Effects 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000007914 intraventricular administration Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 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
- FZWBNHMXJMCXLU-BLAUPYHCSA-N isomaltotriose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O)O1 FZWBNHMXJMCXLU-BLAUPYHCSA-N 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 235000015110 jellies Nutrition 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
- 239000008101 lactose Substances 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- 108010052322 limitin Proteins 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 208000019423 liver disease Diseases 0.000 description 1
- 229960004844 lovastatin Drugs 0.000 description 1
- PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 description 1
- QLJODMDSTUBWDW-UHFFFAOYSA-N lovastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 QLJODMDSTUBWDW-UHFFFAOYSA-N 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229960001428 mercaptopurine Drugs 0.000 description 1
- 208000030159 metabolic disease Diseases 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 208000021039 metastatic melanoma Diseases 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- PMLZNMUXVYXCNF-UHFFFAOYSA-N methyl 5-amino-2-(2-pyrrolidin-1-ylethoxy)benzoate Chemical compound COC(=O)C1=CC(N)=CC=C1OCCN1CCCC1 PMLZNMUXVYXCNF-UHFFFAOYSA-N 0.000 description 1
- MXUHMQZOATZRIK-UHFFFAOYSA-N methyl 5-amino-2-hydroxybenzoate Chemical compound COC(=O)C1=CC(N)=CC=C1O MXUHMQZOATZRIK-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 210000004688 microtubule Anatomy 0.000 description 1
- 231100000782 microtubule inhibitor Toxicity 0.000 description 1
- 229960001156 mitoxantrone 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
- 210000001616 monocyte Anatomy 0.000 description 1
- 230000002969 morbid Effects 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 239000002324 mouth wash Substances 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- 208000025113 myeloid leukemia Diseases 0.000 description 1
- ZRVSVNBJKUWLCW-UHFFFAOYSA-N n-(1,3-benzodioxol-4-yl)-2-chloro-5-methylpyrimidin-4-amine Chemical compound CC1=CN=C(Cl)N=C1NC1=CC=CC2=C1OCO2 ZRVSVNBJKUWLCW-UHFFFAOYSA-N 0.000 description 1
- OEOMRXZYYISPRB-UHFFFAOYSA-N n-(1,3-benzodioxol-5-yl)-2-chloro-5-methylpyrimidin-4-amine Chemical compound CC1=CN=C(Cl)N=C1NC1=CC=C(OCO2)C2=C1 OEOMRXZYYISPRB-UHFFFAOYSA-N 0.000 description 1
- SABMNKAFZXIAKN-UHFFFAOYSA-N n-(1-benzothiophen-3-yl)-2-chloro-5-methylpyrimidin-4-amine Chemical compound CC1=CN=C(Cl)N=C1NC1=CSC2=CC=CC=C12 SABMNKAFZXIAKN-UHFFFAOYSA-N 0.000 description 1
- OQJZGYXSRKRKLL-UHFFFAOYSA-N n-(1-benzothiophen-5-yl)-2-chloro-5-methylpyrimidin-4-amine Chemical compound CC1=CN=C(Cl)N=C1NC1=CC=C(SC=C2)C2=C1 OQJZGYXSRKRKLL-UHFFFAOYSA-N 0.000 description 1
- KSPFHLWLBKZTOF-UHFFFAOYSA-N n-(3-tert-butylphenyl)-2-chloro-5-methylpyrimidin-4-amine Chemical compound CC1=CN=C(Cl)N=C1NC1=CC=CC(C(C)(C)C)=C1 KSPFHLWLBKZTOF-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- OHDXDNUPVVYWOV-UHFFFAOYSA-N n-methyl-1-(2-naphthalen-1-ylsulfanylphenyl)methanamine Chemical compound CNCC1=CC=CC=C1SC1=CC=CC2=CC=CC=C12 OHDXDNUPVVYWOV-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- VINYOUWDZHOVFB-UHFFFAOYSA-N n-tert-butyl-3-[(2-chloro-5-methylpyrimidin-4-yl)amino]benzenesulfonamide Chemical compound CC1=CN=C(Cl)N=C1NC1=CC=CC(S(=O)(=O)NC(C)(C)C)=C1 VINYOUWDZHOVFB-UHFFFAOYSA-N 0.000 description 1
- CXDSYVZCLNDCGG-UHFFFAOYSA-N n-tert-butyl-3-[[2-(4-imidazol-1-ylanilino)-5-methylpyrimidin-4-yl]amino]benzenesulfonamide Chemical compound N1=C(NC=2C=C(C=CC=2)S(=O)(=O)NC(C)(C)C)C(C)=CN=C1NC(C=C1)=CC=C1N1C=CN=C1 CXDSYVZCLNDCGG-UHFFFAOYSA-N 0.000 description 1
- VHVHGHZSQQLXTI-UHFFFAOYSA-N n-tert-butyl-3-[[5-methyl-2-[4-(pyrazol-1-ylmethyl)anilino]pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound N1=C(NC=2C=C(C=CC=2)S(=O)(=O)NC(C)(C)C)C(C)=CN=C1NC(C=C1)=CC=C1CN1C=CC=N1 VHVHGHZSQQLXTI-UHFFFAOYSA-N 0.000 description 1
- RIWWXOVCJYUCFK-UHFFFAOYSA-N n-tert-butyl-3-[[5-methyl-2-[4-[(4-methylpiperazin-1-yl)methyl]anilino]pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound C1CN(C)CCN1CC(C=C1)=CC=C1NC1=NC=C(C)C(NC=2C=C(C=CC=2)S(=O)(=O)NC(C)(C)C)=N1 RIWWXOVCJYUCFK-UHFFFAOYSA-N 0.000 description 1
- ZSWSYKQYVYOUAE-UHFFFAOYSA-N n-tert-butyl-5-[(2-chloro-5-methylpyrimidin-4-yl)amino]-2-methylbenzenesulfonamide Chemical compound CC1=CN=C(Cl)N=C1NC1=CC=C(C)C(S(=O)(=O)NC(C)(C)C)=C1 ZSWSYKQYVYOUAE-UHFFFAOYSA-N 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 231100000344 non-irritating Toxicity 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000005937 nuclear translocation Effects 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229940045681 other alkylating agent in atc Drugs 0.000 description 1
- 230000002018 overexpression Effects 0.000 description 1
- 238000012261 overproduction Methods 0.000 description 1
- 125000005254 oxyacyl group Chemical group 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 229960002340 pentostatin Drugs 0.000 description 1
- 210000004214 philadelphia chromosome Anatomy 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical compound O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 description 1
- RFIOZSIHFNEKFF-UHFFFAOYSA-N piperazine-1-carboxylic acid Chemical compound OC(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-N 0.000 description 1
- 150000003058 platinum compounds Chemical class 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229940068965 polysorbates Drugs 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- ZTSLXIMJYOKQKX-UHFFFAOYSA-M potassium;2-methoxy-4-nitrophenolate Chemical compound [K+].COC1=CC([N+]([O-])=O)=CC=C1[O-] ZTSLXIMJYOKQKX-UHFFFAOYSA-M 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 229960004618 prednisone Drugs 0.000 description 1
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 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 1
- 239000003790 pyrimidine antagonist Substances 0.000 description 1
- 229940099538 rapamune Drugs 0.000 description 1
- 102000027426 receptor tyrosine kinases Human genes 0.000 description 1
- 108091008598 receptor tyrosine kinases Proteins 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000002207 retinal effect Effects 0.000 description 1
- 150000004508 retinoic acid derivatives Chemical class 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000011808 rodent model Methods 0.000 description 1
- RZJQGNCSTQAWON-UHFFFAOYSA-N rofecoxib Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC=CC=2)C(=O)OC1 RZJQGNCSTQAWON-UHFFFAOYSA-N 0.000 description 1
- 229960000371 rofecoxib Drugs 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
- 125000003607 serino group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C(O[H])([H])[H] 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 229960002855 simvastatin Drugs 0.000 description 1
- RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 description 1
- 230000022379 skeletal muscle tissue development Effects 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 229910001467 sodium calcium phosphate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 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
- 229940083575 sodium dodecyl sulfate Drugs 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 230000000392 somatic effect Effects 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 229940037128 systemic glucocorticoids Drugs 0.000 description 1
- 229960001967 tacrolimus Drugs 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
- 238000002626 targeted therapy Methods 0.000 description 1
- DKPFODGZWDEEBT-QFIAKTPHSA-N taxane Chemical class C([C@]1(C)CCC[C@@H](C)[C@H]1C1)C[C@H]2[C@H](C)CC[C@@H]1C2(C)C DKPFODGZWDEEBT-QFIAKTPHSA-N 0.000 description 1
- 229940063683 taxotere Drugs 0.000 description 1
- LXIKEPCNDFVJKC-QXMHVHEDSA-N tenidap Chemical compound C12=CC(Cl)=CC=C2N(C(=O)N)C(=O)\C1=C(/O)C1=CC=CS1 LXIKEPCNDFVJKC-QXMHVHEDSA-N 0.000 description 1
- 229960003676 tenidap Drugs 0.000 description 1
- 229960001278 teniposide Drugs 0.000 description 1
- WXDHETYREQPFEV-UHFFFAOYSA-N tert-butyl 4-(2-methoxycarbonyl-4-nitrophenyl)piperazine-1-carboxylate Chemical compound COC(=O)C1=CC([N+]([O-])=O)=CC=C1N1CCN(C(=O)OC(C)(C)C)CC1 WXDHETYREQPFEV-UHFFFAOYSA-N 0.000 description 1
- JURSECFDRGRMDW-UHFFFAOYSA-N tert-butyl 4-(4-amino-2-methoxycarbonylphenyl)piperazine-1-carboxylate Chemical compound COC(=O)C1=CC(N)=CC=C1N1CCN(C(=O)OC(C)(C)C)CC1 JURSECFDRGRMDW-UHFFFAOYSA-N 0.000 description 1
- YRLQFRXDWBFGMK-UHFFFAOYSA-N tert-butyl 4-(4-aminophenyl)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1=CC=C(N)C=C1 YRLQFRXDWBFGMK-UHFFFAOYSA-N 0.000 description 1
- VKSINZNBWVJILC-UHFFFAOYSA-N tert-butyl 4-[(3-aminophenyl)methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1CC1=CC=CC(N)=C1 VKSINZNBWVJILC-UHFFFAOYSA-N 0.000 description 1
- SBWYSHUQLRFTDA-UHFFFAOYSA-N tert-butyl 4-[(3-bromophenyl)sulfonylamino]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1NS(=O)(=O)C1=CC=CC(Br)=C1 SBWYSHUQLRFTDA-UHFFFAOYSA-N 0.000 description 1
- LBINQTBOHAQDQT-UHFFFAOYSA-N tert-butyl 4-[3-[[4-(4-chloro-3-methoxyanilino)-5-methylpyrimidin-2-yl]amino]phenyl]piperazine-1-carboxylate Chemical compound C1=C(Cl)C(OC)=CC(NC=2C(=CN=C(NC=3C=C(C=CC=3)N3CCN(CC3)C(=O)OC(C)(C)C)N=2)C)=C1 LBINQTBOHAQDQT-UHFFFAOYSA-N 0.000 description 1
- LYVAUORYRYXEEW-UHFFFAOYSA-N tert-butyl 4-[4-[(4-amino-5-methylpyrimidin-2-yl)amino]phenoxy]piperidine-1-carboxylate Chemical compound N1=C(N)C(C)=CN=C1NC(C=C1)=CC=C1OC1CCN(C(=O)OC(C)(C)C)CC1 LYVAUORYRYXEEW-UHFFFAOYSA-N 0.000 description 1
- PYQPVPBYELLURV-UHFFFAOYSA-N tert-butyl 4-[4-amino-2-(trifluoromethyl)phenyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1=CC=C(N)C=C1C(F)(F)F PYQPVPBYELLURV-UHFFFAOYSA-N 0.000 description 1
- ALKVLJPJNKSFIE-UHFFFAOYSA-N tert-butyl 4-[[3-[[4-(4-chloro-3-methoxyanilino)-5-methylpyrimidin-2-yl]amino]phenyl]methyl]piperazine-1-carboxylate Chemical compound C1=C(Cl)C(OC)=CC(NC=2C(=CN=C(NC=3C=C(CN4CCN(CC4)C(=O)OC(C)(C)C)C=CC=3)N=2)C)=C1 ALKVLJPJNKSFIE-UHFFFAOYSA-N 0.000 description 1
- ADWUHGOUJRQMOC-UHFFFAOYSA-N tert-butyl 4-[[4-[(4-amino-5-methylpyrimidin-2-yl)amino]phenyl]methyl]piperazine-1-carboxylate Chemical compound N1=C(N)C(C)=CN=C1NC(C=C1)=CC=C1CN1CCN(C(=O)OC(C)(C)C)CC1 ADWUHGOUJRQMOC-UHFFFAOYSA-N 0.000 description 1
- LZRDHSFPLUWYAX-UHFFFAOYSA-N tert-butyl 4-aminopiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(N)CC1 LZRDHSFPLUWYAX-UHFFFAOYSA-N 0.000 description 1
- PBWDRTGTQIXVBR-UHFFFAOYSA-N tert-butyl 5-bromoindole-1-carboxylate Chemical compound BrC1=CC=C2N(C(=O)OC(C)(C)C)C=CC2=C1 PBWDRTGTQIXVBR-UHFFFAOYSA-N 0.000 description 1
- FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 1
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229960001196 thiotepa Drugs 0.000 description 1
- 229940044693 topoisomerase inhibitor Drugs 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 229960000575 trastuzumab Drugs 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 229940046728 tumor necrosis factor alpha inhibitor Drugs 0.000 description 1
- 239000002452 tumor necrosis factor alpha inhibitor Substances 0.000 description 1
- 102000003298 tumor necrosis factor receptor Human genes 0.000 description 1
- 229940121358 tyrosine kinase inhibitor Drugs 0.000 description 1
- 239000005483 tyrosine kinase inhibitor Substances 0.000 description 1
- 150000004917 tyrosine kinase inhibitor derivatives Chemical class 0.000 description 1
- 210000001113 umbilicus Anatomy 0.000 description 1
- VBEQCZHXXJYVRD-GACYYNSASA-N uroanthelone Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CS)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CS)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)C(C)C)[C@@H](C)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCSC)NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)CNC(=O)CNC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CS)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CS)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC(N)=O)C(C)C)[C@@H](C)CC)C1=CC=C(O)C=C1 VBEQCZHXXJYVRD-GACYYNSASA-N 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 230000004218 vascular function Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 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
- 230000003612 virological effect Effects 0.000 description 1
- 230000004393 visual impairment Effects 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/12—Keratolytics, e.g. wart or anti-corn preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—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
- A61P25/28—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
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/02—Antidotes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P41/00—Drugs used in surgical methods, e.g. surgery adjuvants for preventing adhesion or for vitreum substitution
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/14—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/06—Antianaemics
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/06—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with radicals, containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
- C07D239/49—Two nitrogen atoms with an aralkyl radical, or substituted aralkyl radical, attached in position 5, e.g. trimethoprim
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Virology (AREA)
- Immunology (AREA)
- Neurology (AREA)
- Diabetes (AREA)
- Neurosurgery (AREA)
- Oncology (AREA)
- Biomedical Technology (AREA)
- Hematology (AREA)
- Pulmonology (AREA)
- Communicable Diseases (AREA)
- Molecular Biology (AREA)
- Dermatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Biotechnology (AREA)
- Cardiology (AREA)
- Endocrinology (AREA)
- Psychology (AREA)
- Epidemiology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Emergency Medicine (AREA)
- Ophthalmology & Optometry (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BR122021011788-8A BR122021011788B1 (pt) | 2005-11-01 | 2006-10-26 | Inibidores de biaril meta pirimidina de cinases, composição farmacêutica e processo para preparar uma composição farmacêutica |
| BR122021011787-0A BR122021011787B1 (pt) | 2005-11-01 | 2006-10-26 | Inibidores de biaril meta pirimidina de cinases, composição farmacêutica e processo para preparar uma composição farmacêutica |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US73262905P | 2005-11-01 | 2005-11-01 | |
| US60/732,629 | 2005-11-01 | ||
| US83800306P | 2006-08-15 | 2006-08-15 | |
| US60/838,003 | 2006-08-15 | ||
| PCT/US2006/042044 WO2007053452A1 (en) | 2005-11-01 | 2006-10-26 | Bi-aryl meta-pyrimidine inhibitors of kinases |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BRPI0618179A2 true BRPI0618179A2 (pt) | 2011-08-23 |
Family
ID=38006192
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0618179-1A BRPI0618179A2 (pt) | 2005-11-01 | 2006-10-26 | inibidores de biaril meta pirimidina de cinases |
| BR122021011788-8A BR122021011788B1 (pt) | 2005-11-01 | 2006-10-26 | Inibidores de biaril meta pirimidina de cinases, composição farmacêutica e processo para preparar uma composição farmacêutica |
| BR122021011787-0A BR122021011787B1 (pt) | 2005-11-01 | 2006-10-26 | Inibidores de biaril meta pirimidina de cinases, composição farmacêutica e processo para preparar uma composição farmacêutica |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BR122021011788-8A BR122021011788B1 (pt) | 2005-11-01 | 2006-10-26 | Inibidores de biaril meta pirimidina de cinases, composição farmacêutica e processo para preparar uma composição farmacêutica |
| BR122021011787-0A BR122021011787B1 (pt) | 2005-11-01 | 2006-10-26 | Inibidores de biaril meta pirimidina de cinases, composição farmacêutica e processo para preparar uma composição farmacêutica |
Country Status (25)
| Country | Link |
|---|---|
| US (3) | US7528143B2 (enExample) |
| EP (1) | EP1951684B1 (enExample) |
| JP (2) | JP5191391B2 (enExample) |
| KR (2) | KR101494468B1 (enExample) |
| CN (1) | CN103626742B (enExample) |
| AU (1) | AU2006309013B2 (enExample) |
| BR (3) | BRPI0618179A2 (enExample) |
| CA (1) | CA2628283C (enExample) |
| CY (2) | CY1118330T1 (enExample) |
| DK (1) | DK1951684T3 (enExample) |
| ES (1) | ES2595636T3 (enExample) |
| FI (1) | FIC20210010I1 (enExample) |
| HU (2) | HUE028987T2 (enExample) |
| IL (1) | IL191167A (enExample) |
| LT (2) | LT1951684T (enExample) |
| MX (2) | MX362412B (enExample) |
| MY (1) | MY167260A (enExample) |
| NL (1) | NL301104I2 (enExample) |
| NO (1) | NO342221B1 (enExample) |
| NZ (2) | NZ592990A (enExample) |
| PL (1) | PL1951684T3 (enExample) |
| PT (1) | PT1951684T (enExample) |
| RU (2) | RU2597364C2 (enExample) |
| TW (1) | TWI444368B (enExample) |
| WO (1) | WO2007053452A1 (enExample) |
Families Citing this family (336)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI329105B (en) | 2002-02-01 | 2010-08-21 | Rigel Pharmaceuticals Inc | 2,4-pyrimidinediamine compounds and their uses |
| RS51752B (sr) | 2002-07-29 | 2011-12-31 | Rigel Pharmaceuticals | Metode tretiranja i prevencije autoimunih oboljenja jedinjenjima 2,4-pirimidindiamina |
| US20050282814A1 (en) * | 2002-10-03 | 2005-12-22 | Targegen, Inc. | Vasculostatic agents and methods of use thereof |
| CA2500727A1 (en) * | 2002-10-03 | 2004-04-15 | Targegen, Inc. | Vasculostatic agents and methods of use thereof |
| HRP20130602T1 (en) | 2003-07-30 | 2013-07-31 | Rigel Pharmaceuticals, Inc. | 2,4-pyrimidinediamine compounds for use in the treatment or prevention of autoimmune diseases |
| NZ551027A (en) * | 2004-04-08 | 2011-01-28 | Targegen Inc | Benzotriazine inhibitors of kinases |
| MX2007002208A (es) | 2004-08-25 | 2007-05-08 | Targegen Inc | Compuestos hetrociclicos y metodos de uso. |
| DE602006010979D1 (de) | 2005-01-19 | 2010-01-21 | Rigel Pharmaceuticals Inc | Prodrugs aus 2,4-pyrimidindiamin-verbindungen und ihre verwendungen |
| CA2608367C (en) | 2005-06-08 | 2014-08-19 | Rigel Pharmaceuticals, Inc. | Compositions and methods for inhibition of the jak pathway |
| US20070203161A1 (en) | 2006-02-24 | 2007-08-30 | Rigel Pharmaceuticals, Inc. | Compositions and methods for inhibition of the jak pathway |
| CA2611720A1 (en) * | 2005-06-08 | 2006-12-14 | Targegen, Inc. | Methods and compositions for the treatment of ocular disorders |
| MX362412B (es) * | 2005-11-01 | 2019-01-15 | Targegen Inc | Inhibidores de biaril meta-pirimidina de cinasas. |
| US8133900B2 (en) * | 2005-11-01 | 2012-03-13 | Targegen, Inc. | Use of bi-aryl meta-pyrimidine inhibitors of kinases |
| US8604042B2 (en) * | 2005-11-01 | 2013-12-10 | Targegen, Inc. | Bi-aryl meta-pyrimidine inhibitors of kinases |
| WO2007056023A2 (en) * | 2005-11-02 | 2007-05-18 | Targegen, Inc. | Thiazole inhibitors targeting resistant kinase mutations |
| ATE525374T1 (de) | 2005-12-13 | 2011-10-15 | Incyte Corp | Heteroarylsubstituierte pyrroloä2,3-büpyridine und pyrroloä2,3-büpyrimidine als januskinaseinhibitoren |
| ES2622493T3 (es) | 2006-02-24 | 2017-07-06 | Rigel Pharmaceuticals, Inc. | Composiciones y métodos para la inhibición de la ruta de JAK |
| US7691858B2 (en) * | 2006-04-25 | 2010-04-06 | Targegen, Inc. | Kinase inhibitors and methods of use thereof |
| WO2008008234A1 (en) * | 2006-07-07 | 2008-01-17 | Targegen, Inc. | 2-amino-5-substituted pyrimidine inhibitors |
| ES2633318T3 (es) | 2006-10-23 | 2017-09-20 | Cephalon, Inc. | Derivados bicíclicos fusionados de 2,4-diaminopirimidina como inhibidores de ALK y c-Met |
| KR20090082502A (ko) | 2006-12-22 | 2009-07-30 | 에프. 호프만-라 로슈 아게 | 스피로-피페리딘 유도체 |
| TW200840581A (en) * | 2007-02-28 | 2008-10-16 | Astrazeneca Ab | Novel pyrimidine derivatives |
| US20080214558A1 (en) * | 2007-03-01 | 2008-09-04 | Supergen, Inc. | Pyrimidine-2,4-diamine derivatives and their use as jak2 kinase inhibitors |
| WO2008118822A1 (en) * | 2007-03-23 | 2008-10-02 | Rigel Pharmaceuticals, Inc. | Compositions and methods for inhibition of the jak pathway |
| ES2467665T5 (es) | 2007-06-13 | 2022-11-03 | Incyte Holdings Corp | Sales del inhibidor de cinasas Janus (R)-3-(4-(7H-pirrolo[2,3-d]pirimidin-4-il)-1H-pirazol-1-il)-3-ciclopentilpropanonitrilo |
| BRPI0814821A2 (pt) * | 2007-07-16 | 2015-02-03 | Astrazeneca Ab | Composto, composição farmacêutica, e, processo para preparar um composto |
| EP2183225A1 (en) | 2007-07-17 | 2010-05-12 | Rigel Pharmaceuticals, Inc. | Cyclic amine substituted pyrimidinediamines as pkc inhibitors |
| KR101174201B1 (ko) | 2007-08-28 | 2012-08-16 | 아이알엠 엘엘씨 | 키나제 억제제로서의 2-비페닐아미노-4-아미노피리미딘 유도체 |
| CA2960659C (en) * | 2007-11-09 | 2021-07-13 | The Salk Institute For Biological Studies | Use of tam receptor inhibitors as immunoenhancers and tam activators as immunosuppressors |
| US20100310563A1 (en) * | 2007-11-30 | 2010-12-09 | Bumm Thomas G P | Methods for treating induced cellular proliferative disorders |
| AU2009203773B2 (en) | 2008-01-11 | 2013-04-18 | F. Hoffmann-La Roche Ag | Modulators for amyloid beta |
| EP2257541B1 (en) * | 2008-02-22 | 2013-08-14 | F. Hoffmann-La Roche AG | Modulators for amyloid beta |
| AU2009215430B2 (en) | 2008-02-22 | 2015-02-12 | Rigel Pharmaceuticals, Inc. | Use of 2,4-pyrimidinediamines for the treatment of atherosclerosis |
| CA2723358A1 (en) * | 2008-05-05 | 2009-11-12 | Allison B. Reiss | Method for improving cardiovascular risk profile of cox inhibitors |
| US9273077B2 (en) | 2008-05-21 | 2016-03-01 | Ariad Pharmaceuticals, Inc. | Phosphorus derivatives as kinase inhibitors |
| WO2009143389A1 (en) | 2008-05-21 | 2009-11-26 | Ariad Pharmaceuticals, Inc. | Phosphorous derivatives as kinase inhibitors |
| PE20100087A1 (es) | 2008-06-25 | 2010-02-08 | Irm Llc | Compuestos y composiciones como inhibidores de cinasa |
| US8450335B2 (en) | 2008-06-27 | 2013-05-28 | Celgene Avilomics Research, Inc. | 2,4-disubstituted pyrimidines useful as kinase inhibitors |
| US8338439B2 (en) * | 2008-06-27 | 2012-12-25 | Celgene Avilomics Research, Inc. | 2,4-disubstituted pyrimidines useful as kinase inhibitors |
| US11351168B1 (en) | 2008-06-27 | 2022-06-07 | Celgene Car Llc | 2,4-disubstituted pyrimidines useful as kinase inhibitors |
| US20100029675A1 (en) * | 2008-07-25 | 2010-02-04 | Hwang Soo-In | Pyrimidine-2, 4-diamine JAK2 Kinase inhibiting anti-inflammation use |
| US20110269721A1 (en) * | 2008-08-05 | 2011-11-03 | Targegen, Inc. | Methods of treating thalassemia |
| 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. |
| CA2736924C (en) | 2008-10-09 | 2016-06-28 | F. Hoffmann-La Roche Ag | Modulators for amyloid beta |
| JP5378532B2 (ja) | 2008-11-10 | 2013-12-25 | エフ.ホフマン−ラ ロシュ アーゲー | 複素環γ−セクレターゼモジュレーター |
| WO2010077740A2 (en) * | 2008-12-09 | 2010-07-08 | Cytokine Pharmasciences, Inc. | Novel antiviral compounds, compositions, and methods of use |
| WO2010093808A1 (en) | 2009-02-11 | 2010-08-19 | Reaction Biology Corp. | Selective kinase inhibitors |
| ES2423804T3 (es) * | 2009-04-03 | 2013-09-24 | Cellzome Gmbh | Métodos para la identificación de moléculas que interaccionan con cinasas y para la purificación de proteínas de cinasa |
| US20120040955A1 (en) * | 2009-04-14 | 2012-02-16 | Richard John Harrison | Fluoro substituted pyrimidine compounds as jak3 inhibitors |
| JP5918693B2 (ja) | 2009-05-05 | 2016-05-18 | ダナ ファーバー キャンサー インスティテュート インコーポレイテッド | Egfr阻害剤及び疾患の治療方法 |
| WO2010129802A1 (en) * | 2009-05-06 | 2010-11-11 | Portola Pharmaceuticals, Inc. | Inhibitors of jak |
| JP6172939B2 (ja) * | 2009-05-22 | 2017-08-02 | インサイト・ホールディングス・コーポレイションIncyte Holdings Corporation | Jak阻害薬としての3−[4−(7h−ピロロ[2,3−d]ピリミジン−4−イル)−1h−ピラゾール−1−イル]オクタン−またはヘプタン−ニトリル |
| WO2010135650A1 (en) | 2009-05-22 | 2010-11-25 | Incyte Corporation | N-(HETERO)ARYL-PYRROLIDINE DERIVATIVES OF PYRAZOL-4-YL-PYRROLO[2,3-d]PYRIMIDINES AND PYRROL-3-YL-PYRROLO[2,3-d]PYRIMIDINES AS JANUS KINASE INHIBITORS |
| CN102482278B (zh) | 2009-06-29 | 2015-04-22 | 因塞特公司 | 作为pi3k抑制剂的嘧啶酮类 |
| JP2012197231A (ja) * | 2009-08-06 | 2012-10-18 | Oncotherapy Science Ltd | Ttk阻害作用を有するピリジンおよびピリミジン誘導体 |
| TW201113285A (en) | 2009-09-01 | 2011-04-16 | Incyte Corp | Heterocyclic derivatives of pyrazol-4-yl-pyrrolo[2,3-d]pyrimidines as janus kinase inhibitors |
| EP3461824B1 (en) * | 2009-09-04 | 2021-08-25 | Biogen MA Inc. | Bruton's tyrosine kinase inhibitors |
| EP2475648A1 (en) * | 2009-09-11 | 2012-07-18 | Cellzome Limited | Ortho substituted pyrimidine compounds as jak inhibitors |
| NZ620174A (en) | 2009-09-16 | 2016-08-26 | Celgene Avilomics Res Inc | Protein kinase conjugates and inhibitors |
| MX2012004379A (es) * | 2009-10-15 | 2012-06-01 | Pfizer | Compuestos de pirrolo[2,3-d]pirimidina. |
| MX2012005155A (es) | 2009-11-03 | 2012-08-31 | Glaxosmithkline Llc | Compuestos de quinazolina. |
| WO2011056739A1 (en) * | 2009-11-03 | 2011-05-12 | Glaxosmithkline Llc | Compounds and methods |
| AU2010333024B2 (en) * | 2009-12-14 | 2014-09-18 | Merck Sharp & Dohme B.V. | MK2 inhibitors |
| WO2011075643A1 (en) | 2009-12-18 | 2011-06-23 | Incyte Corporation | Substituted heteroaryl fused derivatives as pi3k inhibitors |
| ES2461967T3 (es) | 2009-12-18 | 2014-05-21 | Pfizer Inc. | Compuestos de pirrolo[2,3-d]pirimidina |
| NZ601021A (en) * | 2009-12-23 | 2014-09-26 | Medicis Pharmaceutical Corp | Aminoalkylpyrimidine derivatives as histamine h4 receptor antagonists |
| EP2519664A4 (en) | 2009-12-30 | 2014-03-12 | Avila Therapeutics Inc | LIGAND-RELATED COVALENTS MODIFYING A PROTEIN |
| US20120329784A1 (en) * | 2010-01-13 | 2012-12-27 | Kallander Lara S | Compounds and methods |
| US8486967B2 (en) | 2010-02-17 | 2013-07-16 | Hoffmann-La Roche Inc. | Heteroaryl substituted piperidines |
| PE20130038A1 (es) | 2010-03-10 | 2013-01-28 | Incyte Corp | Derivados de piperidin-4-il azetidina como inhibidores de jak1 |
| KR101461767B1 (ko) | 2010-03-30 | 2014-11-13 | 노파르티스 아게 | 만성 활성 b-세포-수용체 신호전달이 있는 b-세포 림프종의 치료를 위한 pkc 억제제 |
| EP2558463A1 (en) | 2010-04-14 | 2013-02-20 | Incyte Corporation | Fused derivatives as i3 inhibitors |
| MX354217B (es) | 2010-05-14 | 2018-02-19 | Dana Farber Cancer Inst Inc | Composiciones y metodos para el tratamiento de leucemia. |
| PL2571503T3 (pl) | 2010-05-14 | 2015-06-30 | Dana Farber Cancer Inst Inc | Kompozycje i sposoby leczenia nowotworu, choroby zapalnej i innych zaburzeń |
| CA2799381A1 (en) | 2010-05-14 | 2011-11-17 | Dana-Farber Cancer Institute, Inc. | Male contraceptive compositions and methods of use |
| KR102303885B1 (ko) | 2010-05-21 | 2021-09-24 | 인사이트 홀딩스 코포레이션 | Jak 저해제에 대한 국소 제형 |
| BR112012029647A2 (pt) | 2010-05-21 | 2016-08-02 | Chemilia Ab | novos derivados de pirimidinas |
| WO2011149827A1 (en) * | 2010-05-24 | 2011-12-01 | Glaxosmithkline Llc | Compounds and methods |
| JP6068340B2 (ja) | 2010-08-10 | 2017-01-25 | セルジーン アヴィロミクス リサーチ, インコーポレイテッド | Btk阻害剤のベシル酸塩 |
| NZ710636A (en) | 2010-11-01 | 2017-02-24 | Celgene Avilomics Res Inc | Heterocyclic compounds and uses thereof |
| ES2635713T3 (es) | 2010-11-01 | 2017-10-04 | Celgene Car Llc | Compuestos de heteroarilo y usos de los mismos |
| WO2012060847A1 (en) * | 2010-11-07 | 2012-05-10 | Targegen, Inc. | Compositions and methods for treating myelofibrosis |
| JP5957003B2 (ja) | 2010-11-10 | 2016-07-27 | セルジーン アヴィロミクス リサーチ, インコーポレイテッド | 変異体選択的egfr阻害剤およびその使用 |
| WO2012068440A1 (en) | 2010-11-19 | 2012-05-24 | Incyte Corporation | Heterocyclic-substituted pyrrolopyridines and pyrrolopyrimidines as jak inhibitors |
| EA026201B1 (ru) | 2010-11-19 | 2017-03-31 | Инсайт Холдингс Корпорейшн | Циклобутилзамещенные производные пирролопиридина и пирролопиримидина как ингибиторы jak |
| TW201249844A (en) | 2010-12-20 | 2012-12-16 | Incyte Corp | N-(1-(substituted-phenyl)ethyl)-9H-purin-6-amines as PI3K inhibitors |
| WO2012088266A2 (en) | 2010-12-22 | 2012-06-28 | Incyte Corporation | Substituted imidazopyridazines and benzimidazoles as inhibitors of fgfr3 |
| US9108984B2 (en) * | 2011-03-14 | 2015-08-18 | Incyte Corporation | Substituted diamino-pyrimidine and diamino-pyridine derivatives as PI3K inhibitors |
| BR112013024378A2 (pt) | 2011-03-24 | 2016-12-13 | Chemilia Ab | novos derivados de pirimidina |
| US9126948B2 (en) * | 2011-03-25 | 2015-09-08 | Incyte Holdings Corporation | Pyrimidine-4,6-diamine derivatives as PI3K inhibitors |
| US9249124B2 (en) | 2011-03-30 | 2016-02-02 | H. Lee Moffitt Cancer Center And Research Institute, Inc. | Aurora kinase inhibitors and methods of making and using thereof |
| WO2012135801A1 (en) | 2011-04-01 | 2012-10-04 | University Of Utah Research Foundation | Substituted n-(3-(pyrimidin-4-yl)phenyl)acrylamide analogs as tyrosine receptor kinase btk inhibitors |
| EP2693881B1 (en) * | 2011-04-01 | 2019-09-04 | University of Utah Research Foundation | Substituted n-phenylpyrimidin-2-amine analogs as inhibitors of the axl kinase |
| CN103501612B (zh) | 2011-05-04 | 2017-03-29 | 阿里亚德医药股份有限公司 | 抑制表皮生长因子受体导致的癌症中细胞增殖的化合物 |
| CA2839767A1 (en) | 2011-06-20 | 2012-12-27 | Incyte Corporation | Azetidinyl phenyl, pyridyl or pyrazinyl carboxamide derivatives as jak inhibitors |
| 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 |
| TWI648277B (zh) | 2011-09-02 | 2019-01-21 | 美商英塞特控股公司 | 作為pi3k抑制劑之雜環基胺 |
| UA111854C2 (uk) | 2011-09-07 | 2016-06-24 | Інсайт Холдінгс Корпорейшн | Способи і проміжні сполуки для отримання інгібіторів jak |
| WO2013059548A1 (en) | 2011-10-19 | 2013-04-25 | Sanofi | Compositions and methods for treating cancer using jak2 inhibitor |
| US9364476B2 (en) | 2011-10-28 | 2016-06-14 | Celgene Avilomics Research, Inc. | Methods of treating a Bruton's Tyrosine Kinase disease or disorder |
| CN102429901B (zh) * | 2011-11-03 | 2013-11-06 | 合肥博太医药生物技术发展有限公司 | 吲哚-3-甲醇、二吲哚甲烷及其衍生物在制备防治肾纤维化药物中的应用 |
| ES2698298T3 (es) | 2012-03-15 | 2019-02-04 | Celgene Car Llc | Sales de un inhibidor de quinasa receptor de factor de crecimiento epidérmico |
| ES2880109T3 (es) | 2012-03-15 | 2021-11-23 | Celgene Car Llc | Formas sólidas de un inhibidor de la cinasa del receptor del factor de crecimiento epidérmico |
| AR090548A1 (es) | 2012-04-02 | 2014-11-19 | Incyte Corp | Azaheterociclobencilaminas biciclicas como inhibidores de pi3k |
| JP6469567B2 (ja) | 2012-05-05 | 2019-02-13 | アリアド・ファーマシューティカルズ・インコーポレイテッド | Egfr発動性がんの細胞増殖阻害用化合物 |
| US9193733B2 (en) | 2012-05-18 | 2015-11-24 | Incyte Holdings Corporation | Piperidinylcyclobutyl substituted pyrrolopyridine and pyrrolopyrimidine derivatives as JAK inhibitors |
| AR091273A1 (es) * | 2012-06-08 | 2015-01-21 | Biogen Idec Inc | Inhibidores de pirimidinil tirosina quinasa |
| EP2858500A4 (en) | 2012-06-08 | 2016-04-06 | Biogen Ma Inc | BRUTON TYROSINE KINASE HEMMER |
| UA125503C2 (uk) | 2012-06-13 | 2022-04-13 | Інсайт Холдинґс Корпорейшн | Заміщені трициклічні сполуки як інгібітори fgfr |
| BR112014032346A2 (pt) | 2012-06-26 | 2017-06-27 | Del Mar Pharmaceuticals | métodos para tratamento de malignidades resistentes ao inibidor de tirosina-quinase em pacientes com polimorfismos genéticos ou desregulações de ahi1 mutações empregando dianidrogalactitol, diacetildianidrogalactitol, dibromodulcitol, ou análogos ou derivados destes |
| US9388185B2 (en) | 2012-08-10 | 2016-07-12 | Incyte Holdings Corporation | Substituted pyrrolo[2,3-b]pyrazines as FGFR inhibitors |
| KR102194611B1 (ko) | 2012-10-04 | 2020-12-23 | 유니버시티 오브 유타 리서치 파운데이션 | 티로신 수용체 키나아제 btk 억제제로서 치환된 n-(3-(피리미딘-4-일)페닐)아크릴아미드 유사체 |
| WO2014055934A2 (en) | 2012-10-04 | 2014-04-10 | University Of Utah Research Foundation | Substituted n-(3-(pyrimidin-4-yl)phenyl)acrylamide analogs as tyrosine receptor kinase btk inhibitors |
| RS62329B1 (sr) | 2012-11-15 | 2021-10-29 | Incyte Holdings Corp | Dozni oblici ruksolitiniba sa produženim vremenom oslobađanja |
| US9266892B2 (en) | 2012-12-19 | 2016-02-23 | Incyte Holdings Corporation | Fused pyrazoles as FGFR inhibitors |
| US9126950B2 (en) | 2012-12-21 | 2015-09-08 | Celgene Avilomics Research, Inc. | Heteroaryl compounds and uses thereof |
| PE20151274A1 (es) | 2013-02-08 | 2015-09-12 | Celgene Avilomics Res Inc | Inhibidores de erk y sus usos |
| TR201820520T4 (tr) | 2013-03-06 | 2019-01-21 | Incyte Holdings Corp | Bir jak inhibitörü yapmaya yönelik prosesler ve ara ürünler. |
| JP6433974B2 (ja) | 2013-03-14 | 2018-12-05 | トレロ ファーマシューティカルズ, インコーポレイテッド | Jak2およびalk2阻害剤およびその使用方法 |
| US9714946B2 (en) | 2013-03-14 | 2017-07-25 | Dana-Farber Cancer Institute, Inc. | Bromodomain binding reagents and uses thereof |
| EP2968358A4 (en) * | 2013-03-15 | 2016-08-10 | Ariad Pharma Inc | NOVEL CHOLINKINASE INHIBITORS |
| US9611283B1 (en) | 2013-04-10 | 2017-04-04 | Ariad Pharmaceuticals, Inc. | Methods for inhibiting cell proliferation in ALK-driven cancers |
| US9210831B2 (en) | 2013-04-15 | 2015-12-08 | International Business Machines Corporation | Separable and integrated heat sinks facilitating cooling multi-compnent electronic assembly |
| MY181497A (en) | 2013-04-19 | 2020-12-23 | Incyte Holdings Corp | Bicyclic heterocycles as fgfr inhibitors |
| JP6368777B2 (ja) * | 2013-06-04 | 2018-08-01 | アクチュラム・ライフ・サイエンス・アクチエボラーグ | ピリミジン化合物およびガンマセクレターゼモジュレーターとしてのその使用 |
| MX2016001037A (es) | 2013-07-25 | 2016-11-10 | Dana Farber Cancer Inst Inc | Inhibidores de factores de transcripción y usos. |
| EP3030241A4 (en) * | 2013-08-06 | 2019-06-19 | H. Lee Moffitt Cancer Center And Research Institute, Inc. | INHIBITORS OF ACK1 / TNK2.TYROSINE KINASE |
| DK3030227T3 (da) | 2013-08-07 | 2020-04-20 | Incyte Corp | Vedvarende frigivelses-doseringsformer for en jak1-inhibitor |
| US9492471B2 (en) | 2013-08-27 | 2016-11-15 | Celgene Avilomics Research, Inc. | Methods of treating a disease or disorder associated with Bruton'S Tyrosine Kinase |
| MX379463B (es) | 2013-11-08 | 2025-03-10 | Dana Farber Cancer Inst Inc | Terapia de combinación para el cáncer usando inhibidores de la proteína bromodominio y extra-terminal. |
| SI3080103T1 (sl) | 2013-12-11 | 2018-11-30 | Biogen Ma Inc. | Biarilne spojine, ki so uporabne za zdravljenje človeških bolezni na področju onkologije, nevrologije in imunologije |
| US9415049B2 (en) | 2013-12-20 | 2016-08-16 | Celgene Avilomics Research, Inc. | Heteroaryl compounds and uses thereof |
| US10150756B2 (en) | 2014-01-31 | 2018-12-11 | Dana-Farber Cancer Institute, Inc. | Diaminopyrimidine benzenesulfone derivatives and uses thereof |
| EP3099693A4 (en) | 2014-01-31 | 2017-08-16 | Dana-Farber Cancer Institute, Inc. | Uses of diazepane derivatives |
| JP2017504650A (ja) | 2014-01-31 | 2017-02-09 | ダナ−ファーバー キャンサー インスティテュート, インコーポレイテッド | ジアゼパン誘導体およびその使用 |
| JP2017506666A (ja) | 2014-02-28 | 2017-03-09 | テンシャ セラピューティクス,インコーポレイテッド | 高インスリン血症に関連した症状の処置 |
| AU2015222865B2 (en) | 2014-02-28 | 2019-06-20 | Takeda Pharmaceutical Company Limited | TYK2 inhibitors and uses thereof |
| 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 |
| WO2015191677A1 (en) | 2014-06-11 | 2015-12-17 | Incyte Corporation | Bicyclic heteroarylaminoalkyl phenyl derivatives as pi3k inhibitors |
| US10106507B2 (en) | 2014-08-03 | 2018-10-23 | H. Lee Moffitt Cancer Center and Research Insitute, Inc. | Potent dual BRD4-kinase inhibitors as cancer therapeutics |
| RU2017104897A (ru) | 2014-08-08 | 2018-09-10 | Дана-Фарбер Кэнсер Инститьют, Инк. | Производные диазепана и их применения |
| WO2016022970A1 (en) | 2014-08-08 | 2016-02-11 | Dana-Farber Cancer Institute, Inc. | Dihydropteridinone derivatives and uses thereof |
| EP3180349B1 (en) | 2014-08-12 | 2025-03-12 | Monash University | Lymph directing prodrugs and therapeutic uses thereof |
| WO2016025561A1 (en) | 2014-08-13 | 2016-02-18 | Celgene Avilomics Research, Inc. | Forms and compositions of an erk inhibitor |
| TWI679205B (zh) | 2014-09-02 | 2019-12-11 | 日商日本新藥股份有限公司 | 吡唑并噻唑化合物及醫藥 |
| US10851105B2 (en) | 2014-10-22 | 2020-12-01 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| EP3212654B1 (en) | 2014-10-27 | 2020-04-08 | Tensha Therapeutics, Inc. | Bromodomain inhibitors |
| US10480375B2 (en) | 2014-10-28 | 2019-11-19 | Cummins Emission Solutions Inc. | SCR conversion efficiency diagnostics |
| BR112017008575B1 (pt) | 2014-10-29 | 2021-07-13 | Bicyclerd Limited | Ligantes de peptídeos bicíclicos específicos a mt1-mmp, conjugado de fármaco, processo para preparação de um conjugado de fármaco e composição farmacêutica |
| CR20170390A (es) | 2015-02-20 | 2017-10-23 | Incyte Holdings Corp | Heterociclos biciclicos como inhibidores de fgfr |
| MA41551A (fr) | 2015-02-20 | 2017-12-26 | Incyte Corp | Hétérocycles bicycliques utilisés en tant qu'inhibiteurs de fgfr4 |
| US9580423B2 (en) | 2015-02-20 | 2017-02-28 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| CA3285092A1 (en) | 2015-02-27 | 2025-11-29 | Incyte Holdings Corporation | Salts of pi3k inhibitor and processes for their preparation |
| ES2930585T3 (es) | 2015-02-27 | 2022-12-19 | Nimbus Lakshmi Inc | Inhibidores de TYK2 y usos de los mismos |
| US9988401B2 (en) | 2015-05-11 | 2018-06-05 | Incyte Corporation | Crystalline forms of a PI3K inhibitor |
| US9732097B2 (en) | 2015-05-11 | 2017-08-15 | Incyte Corporation | Process for the synthesis of a phosphoinositide 3-kinase inhibitor |
| CA2986441A1 (en) | 2015-06-12 | 2016-12-15 | Dana-Farber Cancer Institute, Inc. | Combination therapy of transcription inhibitors and kinase inhibitors |
| WO2017004134A1 (en) | 2015-06-29 | 2017-01-05 | Nimbus Iris, Inc. | Irak inhibitors and uses thereof |
| KR102591886B1 (ko) * | 2015-07-21 | 2023-10-20 | 광저우 맥시노벨 파마수티컬스 씨오., 엘티디. | 축합고리 피리미딘계 화합물, 중간체, 이의 제조 방법, 조성물 및 응용 |
| WO2017040757A1 (en) | 2015-09-02 | 2017-03-09 | Nimbus Lakshmi, Inc. | Tyk2 inhibitors and uses thereof |
| CN108137482B (zh) | 2015-09-08 | 2024-03-15 | 莫纳什大学 | 定向淋巴的前药 |
| WO2017044720A1 (en) | 2015-09-11 | 2017-03-16 | Navitor Pharmaceuticals, Inc. | Rapamycin analogs and uses thereof |
| PE20181287A1 (es) | 2015-09-11 | 2018-08-07 | Dana Farber Cancer Inst Inc | Ciano tienotriazolpirazinas y usos de las mismas |
| RU2018112953A (ru) | 2015-09-11 | 2019-10-14 | Дана-Фарбер Кэнсер Инститьют, Инк. | Ацетамидтиенотриазолодиазепины и пути их применения |
| US10738016B2 (en) | 2015-10-13 | 2020-08-11 | H. Lee Moffitt Cancer Center And Research Institute, Inc. | BRD4-kinase inhibitors as cancer therapeutics |
| WO2017070518A1 (en) | 2015-10-23 | 2017-04-27 | Navitor Pharmaceuticals, Inc. | Modulators of sestrin-gator2 interaction and uses thereof |
| CN108472298B (zh) | 2015-11-24 | 2021-04-20 | 深圳阿拉丁医疗科技有限公司 | 选择性激酶抑制剂 |
| US10913752B2 (en) | 2015-11-25 | 2021-02-09 | Dana-Farber Cancer Institute, Inc. | Bivalent bromodomain inhibitors and uses thereof |
| GB201521919D0 (en) | 2015-12-11 | 2016-01-27 | Electrophoretics Ltd | Isobaric mass labels |
| EP3389664A4 (en) | 2015-12-14 | 2020-01-08 | Raze Therapeutics Inc. | MTHFD2 CAFFEIN INHIBITORS AND USES THEREOF |
| HUE055197T2 (hu) | 2016-03-09 | 2021-11-29 | Raze Therapeutics Inc | 3-Foszfoglicerát-dehidrogenáz inhibitorok és alkalmazásuk |
| US11014882B2 (en) | 2016-03-09 | 2021-05-25 | Raze Therapeutics, Inc. | 3-phosphoglycerate dehydrogenase inhibitors and uses thereof |
| CA3019394A1 (en) | 2016-04-08 | 2017-10-12 | X4 Pharmaceuticals, Inc. | Methods for treating cancer |
| JP7041070B2 (ja) * | 2016-04-15 | 2022-03-23 | エピザイム,インコーポレイティド | Ehmt1およびehmt2阻害剤としてのアミン置換アリールまたはヘテロアリール化合物 |
| ES2870920T3 (es) | 2016-06-21 | 2021-10-28 | X4 Pharmaceuticals Inc | Inhibidores de CXCR4 y usos de los mismos |
| JP7084624B2 (ja) | 2016-06-21 | 2022-06-15 | エックス4 ファーマシューティカルズ, インコーポレイテッド | Cxcr4阻害剤およびその使用 |
| JP6994767B2 (ja) | 2016-06-21 | 2022-01-14 | エックス4 ファーマシューティカルズ, インコーポレイテッド | Cxcr4阻害剤およびその使用 |
| US11174243B2 (en) | 2016-07-21 | 2021-11-16 | Sunesis Pharmaceuticals, Inc. | Succinate forms and compositions of Bruton's tyrosine kinase inhibitors |
| EP3526222B1 (en) | 2016-10-14 | 2022-08-17 | Nimbus Lakshmi, Inc. | Tyk2 inhibitors and uses thereof |
| EP3528816A4 (en) | 2016-10-21 | 2020-04-08 | Nimbus Lakshmi, Inc. | TYK2 INHIBITORS AND USES THEREOF |
| EP3538091A4 (en) | 2016-11-08 | 2020-06-10 | Navitor Pharmaceuticals, Inc. | PHENYL AMINO PIPERIDINE MTORC INHIBITORS AND USES THEREOF |
| EP3548005A4 (en) | 2016-11-29 | 2020-06-17 | Puretech Health LLC | Exosomes for delivery of therapeutic agents |
| US11091451B2 (en) | 2016-12-05 | 2021-08-17 | Raze Therapeutics, Inc. | SHMT inhibitors and uses thereof |
| CN110603261A (zh) | 2016-12-23 | 2019-12-20 | 拜斯科阿迪有限公司 | 具有新型键结构的肽衍生物 |
| ES2985986T3 (es) | 2017-01-06 | 2024-11-08 | Bicyclerd Ltd | Conjugado biciclo para tratar el cáncer |
| EP3592746B1 (en) | 2017-03-08 | 2024-01-24 | Takeda Pharmaceutical Company Limited | Tyk2 inhibitors, uses, and methods for production thereof |
| EP3375778A1 (en) | 2017-03-14 | 2018-09-19 | Artax Biopharma Inc. | Aryl-piperidine derivatives |
| EP3375784A1 (en) | 2017-03-14 | 2018-09-19 | Artax Biopharma Inc. | Aza-dihydro-acridone derivatives |
| US10342766B2 (en) * | 2017-03-23 | 2019-07-09 | North Carolina Agricultural And Technical State University | 6-shogaol derivatives and activities thereof |
| WO2018191146A1 (en) | 2017-04-10 | 2018-10-18 | Navitor Pharmaceuticals, Inc. | Heteroaryl rheb inhibitors and uses thereof |
| CN110621316B (zh) | 2017-04-21 | 2024-01-26 | Epizyme股份有限公司 | 用ehmt2抑制剂进行的组合疗法 |
| CN110809467B (zh) | 2017-04-26 | 2023-03-10 | 纳维托制药有限公司 | Sestrin-gator2相互作用的调节剂及其用途 |
| US10857196B2 (en) | 2017-04-27 | 2020-12-08 | Bicycletx Limited | Bicyclic peptide ligands and uses thereof |
| AR111960A1 (es) | 2017-05-26 | 2019-09-04 | Incyte Corp | Formas cristalinas de un inhibidor de fgfr y procesos para su preparación |
| CN111032678A (zh) | 2017-06-26 | 2020-04-17 | 拜西克尔德有限公司 | 具有可检测部分的双环肽配体和其用途 |
| WO2019023468A1 (en) | 2017-07-28 | 2019-01-31 | Nimbus Lakshmi, Inc. | TYK2 INHIBITORS AND USES THEREOF |
| CN118772242A (zh) | 2017-08-04 | 2024-10-15 | 拜斯科技术开发有限公司 | Cd137特异性的双环肽配体 |
| US20200291096A1 (en) | 2017-08-14 | 2020-09-17 | Bicyclerd Limited | Bicyclic peptide ligand sting conjugates and uses thereof |
| EP3668550A1 (en) | 2017-08-14 | 2020-06-24 | Bicyclerd Limited | Bicyclic peptide ligand prr-a conjugates and uses thereof |
| EP4306524A3 (en) | 2017-08-29 | 2024-09-11 | PureTech LYT, Inc. | Lymphatic system-directing lipid prodrugs |
| US11883497B2 (en) | 2017-08-29 | 2024-01-30 | Puretech Lyt, Inc. | Lymphatic system-directing lipid prodrugs |
| IL295603B2 (en) | 2017-09-22 | 2024-03-01 | Kymera Therapeutics Inc | Protein degraders and uses thereof |
| EP3684366A4 (en) | 2017-09-22 | 2021-09-08 | Kymera Therapeutics, Inc. | CRBN LIGANDS AND USES OF THE LATEST |
| JP2021500334A (ja) * | 2017-10-18 | 2021-01-07 | エピザイム,インコーポレイティド | Ehmt2阻害剤としてのアミン置換複素環化合物、その塩、及びそれらの合成方法 |
| WO2019113487A1 (en) | 2017-12-08 | 2019-06-13 | Incyte Corporation | Low dose combination therapy for treatment of myeloproliferative neoplasms |
| TWI825046B (zh) | 2017-12-19 | 2023-12-11 | 英商拜西可泰克斯有限公司 | Epha2特用之雙環胜肽配位基 |
| WO2019126378A1 (en) | 2017-12-19 | 2019-06-27 | Ariya Therapeutics, Inc. | Lipid prodrugs of mycophenolic acid and uses thereof |
| US11304954B2 (en) | 2017-12-19 | 2022-04-19 | Puretech Lyt, Inc. | Lipid prodrugs of mycophenolic acid and uses thereof |
| GB201721265D0 (en) | 2017-12-19 | 2018-01-31 | Bicyclerd Ltd | Bicyclic peptide ligands specific for EphA2 |
| US11608345B1 (en) | 2017-12-19 | 2023-03-21 | Puretech Lyt, Inc. | Lipid prodrugs of rapamycin and its analogs and uses thereof |
| IL315310A (en) | 2017-12-26 | 2024-10-01 | Kymera Therapeutics Inc | Irak degraders and uses thereof |
| US11485743B2 (en) | 2018-01-12 | 2022-11-01 | Kymera Therapeutics, Inc. | Protein degraders and uses thereof |
| WO2019140387A1 (en) | 2018-01-12 | 2019-07-18 | Kymera Therapeutics, Inc. | Crbn ligands and uses thereof |
| US11384069B2 (en) | 2018-01-16 | 2022-07-12 | Shenzhen Targetrx, Inc. | Diphenylaminopyrimidine compound for inhibiting kinase activity |
| TWI816742B (zh) | 2018-01-29 | 2023-10-01 | 美商維泰克斯製藥公司 | Gcn2抑制劑及其用途 |
| CN111867581B (zh) | 2018-01-29 | 2023-12-26 | 默克专利股份有限公司 | Gcn2抑制剂及其用途 |
| WO2019152374A1 (en) | 2018-01-30 | 2019-08-08 | Incyte Corporation | Processes for preparing (1 -(3-fluoro-2-(trifluoromethyl)isonicotinyl)piperidine-4-one) |
| WO2019152883A1 (en) * | 2018-02-02 | 2019-08-08 | Padforward Llc | Inhibitors of protein arginine deiminases |
| BR112020014576A2 (pt) | 2018-02-23 | 2020-12-08 | Bicycletx Limited | Ligantes peptídicos bicíclicos multiméricos |
| KR20200140262A (ko) | 2018-02-27 | 2020-12-15 | 아텍스 바이오파마 인코포레이티드 | Tcr-nck 상호 작용의 억제제로서의 크로멘 유도체 |
| CA3095487A1 (en) | 2018-03-30 | 2019-10-03 | Incyte Corporation | Treatment of hidradenitis suppurativa using jak inhibitors |
| AU2019247498A1 (en) | 2018-04-05 | 2020-11-26 | Sumitomo Pharma Oncology, Inc. | AXL kinase inhibitors and use of the same |
| KR102063155B1 (ko) | 2018-04-11 | 2020-01-08 | 한국과학기술연구원 | 우수한 카이네이즈 저해 활성을 보이는 다양한 치환기를 갖는 피리미딘 유도체 |
| ES2919572T3 (es) | 2018-04-24 | 2022-07-27 | Merck Patent Gmbh | Compuestos antiproliferación y usos de los mismos |
| JP7479293B2 (ja) | 2018-04-24 | 2024-05-08 | バーテックス ファーマシューティカルズ インコーポレイテッド | プテリジノン化合物およびその使用 |
| PE20210919A1 (es) | 2018-05-04 | 2021-05-19 | Incyte Corp | Sales de un inhibidor de fgfr |
| BR112020022392A2 (pt) | 2018-05-04 | 2021-02-02 | Incyte Corporation | formas sólidas de um inibidor de fgfr e processos para preparação das mesmas |
| CN120053645A (zh) | 2018-06-01 | 2025-05-30 | 因赛特公司 | 治疗pi3k相关病症的给药方案 |
| SG11202012447YA (en) | 2018-06-15 | 2021-01-28 | Navitor Pharm Inc | Rapamycin analogs and uses thereof |
| US11180531B2 (en) | 2018-06-22 | 2021-11-23 | Bicycletx Limited | Bicyclic peptide ligands specific for Nectin-4 |
| GB201810316D0 (en) | 2018-06-22 | 2018-08-08 | Bicyclerd Ltd | Peptide ligands for binding to EphA2 |
| WO2020010177A1 (en) | 2018-07-06 | 2020-01-09 | Kymera Therapeutics, Inc. | Tricyclic crbn ligands and uses thereof |
| EP3817822A4 (en) | 2018-07-06 | 2022-07-27 | Kymera Therapeutics, Inc. | PROTEIN DEGRADANTS AND USES THEREOF |
| AU2019310590A1 (en) | 2018-07-26 | 2021-01-14 | Sumitomo Pharma Oncology, Inc. | Methods for treating diseases associated with abnormal acvr1 expression and acvr1 inhibitors for use in the same |
| US10548889B1 (en) | 2018-08-31 | 2020-02-04 | X4 Pharmaceuticals, Inc. | Compositions of CXCR4 inhibitors and methods of preparation and use |
| US12030875B2 (en) | 2018-09-07 | 2024-07-09 | PIC Therapeutics, Inc. | EIF4E inhibitors and uses thereof |
| MY209349A (en) | 2018-09-25 | 2025-07-03 | Impact Biomedicines Inc | Methods of treating myeloproliferative disorders |
| WO2020081508A1 (en) | 2018-10-15 | 2020-04-23 | Nimbus Lakshmi, Inc. | Tyk2 inhibitors and uses thereof |
| WO2020084305A1 (en) | 2018-10-23 | 2020-04-30 | Bicycletx Limited | Bicyclic peptide ligands and uses thereof |
| EP3870158A4 (en) | 2018-10-24 | 2022-08-10 | Navitor Pharmaceuticals, Inc. | Polymorphic compounds and uses thereof |
| WO2020092015A1 (en) * | 2018-11-02 | 2020-05-07 | University Of Rochester | Therapeutic mitigation of epithelial infection |
| EP3886904A4 (en) | 2018-11-30 | 2022-07-13 | Kymera Therapeutics, Inc. | IRAQ DEGRADERS AND USES THEREOF |
| CN113271938A (zh) | 2018-11-30 | 2021-08-17 | 林伯士拉克许米公司 | Tyk2抑制剂和其用途 |
| GB201820288D0 (en) | 2018-12-13 | 2019-01-30 | Bicycle Tx Ltd | Bicycle peptide ligaands specific for MT1-MMP |
| GB201820295D0 (en) | 2018-12-13 | 2019-01-30 | Bicyclerd Ltd | Bicyclic peptide ligands specific for MT1-MMP |
| GB201820325D0 (en) | 2018-12-13 | 2019-01-30 | Bicyclerd Ltd | Bicyclic peptide ligands specific for psma |
| EP3670659A1 (en) | 2018-12-20 | 2020-06-24 | Abivax | Biomarkers, and uses in treatment of viral infections, inflammations, or cancer |
| CN113474045A (zh) | 2018-12-21 | 2021-10-01 | 拜斯科技术开发有限公司 | Pd-l1特异性的双环肽配体 |
| CN111362922A (zh) * | 2018-12-26 | 2020-07-03 | 上海喆邺生物科技有限公司 | 2,4-二氨基嘧啶衍生物及其用途 |
| CA3126034A1 (en) | 2019-01-23 | 2020-07-30 | Nimbus Lakshmi, Inc. | Tyk2 inhibitors and uses thereof |
| KR20210145735A (ko) * | 2019-02-12 | 2021-12-02 | 임팩트 바이오메디신스, 인코포레이티드 | Jak2 저해제의 결정질 형태 |
| FR3092581A1 (fr) * | 2019-02-12 | 2020-08-14 | Impact Biomedicines, Inc | Formes cristallines d'un inhibiteur de jak2 |
| WO2020165600A1 (en) | 2019-02-14 | 2020-08-20 | Bicycletx Limited | Bicyclic peptide ligand sting conjugates and uses thereof |
| US11628162B2 (en) | 2019-03-08 | 2023-04-18 | Incyte Corporation | Methods of treating cancer with an FGFR inhibitor |
| KR102866499B1 (ko) * | 2019-03-15 | 2025-10-02 | 더 제너럴 하스피탈 코포레이션 | Tead 전사인자의 신규한 소분자 저해제 |
| CA3135569A1 (en) | 2019-04-02 | 2020-10-08 | Bicycletx Limited | Bicycle toxin conjugates and uses thereof |
| CA3135802A1 (en) | 2019-04-05 | 2020-10-08 | Kymera Therapeutics, Inc. | Stat degraders and uses thereof |
| MX2021014441A (es) | 2019-05-31 | 2022-01-06 | Ikena Oncology Inc | Inhibidores del dominio asociado mejorador de la transcripcion (tead) y usos de los mismos. |
| WO2020257644A1 (en) | 2019-06-21 | 2020-12-24 | Constellation Pharmaceuticals, Inc. | Methods of treating myeloproliferative disorders |
| WO2020256739A1 (en) | 2019-06-21 | 2020-12-24 | Constellation Pharmaceuticals, Inc. | Methods of treating myeloproliferative disorders |
| WO2021091535A1 (en) | 2019-11-05 | 2021-05-14 | Constellation Pharmaceuticals, Inc. | Treating myeloproliferative disorders with cpi-0610 and a jak inhibitor |
| US11591329B2 (en) | 2019-07-09 | 2023-02-28 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| TWI862640B (zh) | 2019-07-30 | 2024-11-21 | 英商拜西可泰克斯有限公司 | 異質雙環肽複合物 |
| US11845724B2 (en) | 2019-09-11 | 2023-12-19 | Vincere Biosciences, Inc. | USP30 inhibitors and uses thereof |
| KR20220105631A (ko) | 2019-09-13 | 2022-07-27 | 님버스 새턴 인코포레이티드 | Hpk1 길항제 및 이의 용도 |
| JP2022549506A (ja) | 2019-09-27 | 2022-11-25 | ディスク・メディシン・インコーポレイテッド | 骨髄線維症および関連状態を処置するための方法 |
| US12122767B2 (en) | 2019-10-01 | 2024-10-22 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| GEP20247679B (en) | 2019-10-14 | 2024-10-10 | Incyte Corp | Bicyclic heterocycles as fgfr inhibitors |
| WO2021076728A1 (en) | 2019-10-16 | 2021-04-22 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| US11306062B2 (en) | 2019-10-29 | 2022-04-19 | Johnson Matthey Public Limited | Forms of fedratinib dihydrochloride |
| BR112022008287A2 (pt) | 2019-11-01 | 2022-07-26 | Navitor Pharm Inc | Métodos de tratamento usando um modulador de mtorc1 |
| PE20221504A1 (es) | 2019-12-04 | 2022-09-30 | Incyte Corp | Derivados de un inhibidor de fgfr |
| JP7720840B2 (ja) | 2019-12-04 | 2025-08-08 | インサイト・コーポレイション | Fgfr阻害剤としての三環式複素環 |
| US11819476B2 (en) | 2019-12-05 | 2023-11-21 | Janssen Pharmaceutica Nv | Rapamycin analogs and uses thereof |
| TW202136251A (zh) | 2019-12-17 | 2021-10-01 | 美商凱麥拉醫療公司 | Irak降解劑及其用途 |
| US11591332B2 (en) | 2019-12-17 | 2023-02-28 | Kymera Therapeutics, Inc. | IRAK degraders and uses thereof |
| CA3162502A1 (en) | 2019-12-23 | 2021-07-01 | Yi Zhang | Smarca degraders and uses thereof |
| WO2021146424A1 (en) | 2020-01-15 | 2021-07-22 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| CN111423419B (zh) * | 2020-01-17 | 2021-12-17 | 温州医科大学 | 一种小分子化合物cyy-260及其在制备抗肿瘤药物中的应用 |
| KR20220149534A (ko) | 2020-02-05 | 2022-11-08 | 퓨어테크 엘와이티, 아이엔씨. | 신경스테로이드의 지질 전구약물 |
| IL296139A (en) | 2020-03-03 | 2022-11-01 | Pic Therapeutics Inc | Eif4e inhibitors and uses thereof |
| MX2022011602A (es) | 2020-03-19 | 2023-01-04 | Kymera Therapeutics Inc | Degradadores de la proteína de homólogo de ratón de minuto 2 (mdm2) y usos de los mismos. |
| EP4149548A4 (en) | 2020-05-13 | 2024-05-08 | Disc Medicine, Inc. | ANTI-HEMOJUVELIN ANTIBODIES (HJV) FOR THE TREATMENT OF MYELOFIBROSIS |
| US11833155B2 (en) | 2020-06-03 | 2023-12-05 | Incyte Corporation | Combination therapy for treatment of myeloproliferative neoplasms |
| TW202210483A (zh) | 2020-06-03 | 2022-03-16 | 美商凱麥拉醫療公司 | Irak降解劑之結晶型 |
| EP4161521A4 (en) | 2020-06-03 | 2024-07-10 | Kymera Therapeutics, Inc. | DEUTERED IRAQ DEGRADERS AND USES THEREOF |
| CN113754591B (zh) * | 2020-06-05 | 2024-01-05 | 山东大学 | 一种hdac、jak和bet三靶点抑制剂及其制备方法和应用 |
| EP3944859A1 (en) | 2020-07-30 | 2022-02-02 | Assistance Publique Hôpitaux de Paris | Method for treating immune toxicities induced by immune checkpoint inhibitors |
| MX2023001588A (es) | 2020-08-17 | 2023-05-03 | Bicycletx Ltd | Conjugados biciclo específicos para nectina-4 y usos de estos. |
| CN112225703B (zh) * | 2020-09-28 | 2022-03-11 | 广州智睿医药科技有限公司 | 一种治疗或预防与lrrk2激酶或异常lrrk2突变激酶活性相关疾病的药物 |
| JP2023546996A (ja) | 2020-10-23 | 2023-11-08 | ニンバス クロソー, インコーポレイテッド | Ctps1阻害剤およびその使用 |
| CN114426542B (zh) * | 2020-10-29 | 2023-06-30 | 苏州亚宝药物研发有限公司 | 取代的二芳基胺化合物及其药物组合物、制备方法和用途 |
| TWI750905B (zh) * | 2020-11-19 | 2021-12-21 | 財團法人國家衛生研究院 | 噻唑化合物作為蛋白質激酶抑制劑 |
| WO2022120353A1 (en) | 2020-12-02 | 2022-06-09 | Ikena Oncology, Inc. | Tead inhibitors and uses thereof |
| AU2021392040A1 (en) | 2020-12-02 | 2023-06-29 | Ikena Oncology, Inc. | Tead inhibitors and uses thereof |
| TW202237119A (zh) | 2020-12-10 | 2022-10-01 | 美商住友製藥腫瘤公司 | Alk﹘5抑制劑和彼之用途 |
| CA3199509A1 (en) | 2020-12-16 | 2023-06-23 | Gopal Krishna | Dosing of fedratinib |
| WO2022143628A1 (zh) * | 2020-12-29 | 2022-07-07 | 上海岸阔医药科技有限公司 | 预防或治疗抗肿瘤剂相关疾病或病症的方法 |
| AR124547A1 (es) | 2020-12-30 | 2023-04-05 | Kymera Therapeutics Inc | Degradadores de irak y sus usos |
| CN112778282B (zh) * | 2021-01-06 | 2022-07-22 | 温州医科大学 | 一种嘧啶类小分子化合物及其应用 |
| MX2023009060A (es) | 2021-02-02 | 2023-09-29 | Liminal Biosciences Ltd | Antagonistas de gpr84 y usos de estos. |
| CA3206499A1 (en) | 2021-02-02 | 2022-08-11 | Liminal Biosciences Limited | Gpr84 antagonists and uses thereof |
| JP2024506909A (ja) | 2021-02-12 | 2024-02-15 | ニンバス サターン, インコーポレイテッド | Hpk1アンタゴニスト及びその使用 |
| IL304905A (en) | 2021-02-15 | 2023-10-01 | Kymera Therapeutics Inc | IRAK4 joints and their uses |
| US12171768B2 (en) | 2021-02-15 | 2024-12-24 | Kymera Therapeutics, Inc. | IRAK4 degraders and uses thereof |
| JP2024507938A (ja) | 2021-02-25 | 2024-02-21 | インパクト バイオメディシンズ インコーポレイテッド | 骨髄線維症の治療としてのbet阻害剤の使用 |
| JP2024509192A (ja) | 2021-03-05 | 2024-02-29 | ニンバス サターン, インコーポレイテッド | Hpk1アンタゴニスト及びその使用 |
| WO2022203466A1 (ko) * | 2021-03-26 | 2022-09-29 | 주식회사 스탠다임 | Lrrk2에 대해 저해 활성을 갖는 신규한 페닐아미노피리미딘 화합물 및 이의 용도 |
| CA3213359A1 (en) * | 2021-03-26 | 2022-09-29 | Bettina FRANZ | Alk-5 inhibitors and uses thereof |
| JP2024513011A (ja) | 2021-03-29 | 2024-03-21 | ニンバス サターン, インコーポレイテッド | Hpk1アンタゴニスト及びその使用 |
| CA3214952A1 (en) | 2021-04-09 | 2022-10-13 | Silvana Marcel LEIT DE MORADEI | Cbl-b modulators and uses thereof |
| TW202304459A (zh) | 2021-04-12 | 2023-02-01 | 美商英塞特公司 | 包含fgfr抑制劑及nectin-4靶向劑之組合療法 |
| EP4323066A1 (en) | 2021-04-16 | 2024-02-21 | Ikena Oncology, Inc. | Mek inhibitors and uses thereof |
| TW202309030A (zh) | 2021-05-07 | 2023-03-01 | 美商凱麥拉醫療公司 | Cdk2降解劑及其用途 |
| CA3220155A1 (en) | 2021-06-09 | 2022-12-15 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
| TW202313611A (zh) | 2021-06-09 | 2023-04-01 | 美商英塞特公司 | 作為fgfr抑制劑之三環雜環 |
| AU2022334296A1 (en) | 2021-08-25 | 2024-03-07 | PIC Therapeutics, Inc. | Eif4e inhibitors and uses thereof |
| WO2023028238A1 (en) | 2021-08-25 | 2023-03-02 | PIC Therapeutics, Inc. | Eif4e inhibitors and uses thereof |
| US20240358722A1 (en) | 2021-09-14 | 2024-10-31 | Impact Biomedicines, Inc. | Methods of administering fedratinib |
| JP2024535867A (ja) * | 2021-09-16 | 2024-10-02 | ロモンド セラピューティクス,インコーポレイテッド | 治療薬としてn-アリールピリミジン-2-アミン誘導体を有する化合物 |
| JP2024540080A (ja) | 2021-10-29 | 2024-10-31 | カイメラ セラピューティクス, インコーポレイテッド | Irak4分解剤およびその合成 |
| WO2023114984A1 (en) | 2021-12-17 | 2023-06-22 | Ikena Oncology, Inc. | Tead inhibitors and uses thereof |
| JP2025504059A (ja) | 2022-01-31 | 2025-02-06 | カイメラ セラピューティクス, インコーポレイテッド | Irakデグレーダー及びその使用 |
| EP4238564A1 (en) * | 2022-03-02 | 2023-09-06 | Bash Biotech Inc | New treatments of renal cell carcinoma |
| WO2023173057A1 (en) | 2022-03-10 | 2023-09-14 | Ikena Oncology, Inc. | Mek inhibitors and uses thereof |
| WO2023173053A1 (en) | 2022-03-10 | 2023-09-14 | Ikena Oncology, Inc. | Mek inhibitors and uses thereof |
| WO2023211889A1 (en) | 2022-04-25 | 2023-11-02 | Ikena Oncology, Inc. | Polymorphic compounds and uses thereof |
| TW202404581A (zh) | 2022-05-25 | 2024-02-01 | 美商醫肯納腫瘤學公司 | Mek抑制劑及其用途 |
| CN119894873A (zh) | 2022-08-02 | 2025-04-25 | 里米诺生物科学有限公司 | 芳基三唑基和相关gpr84拮抗剂及其用途 |
| AU2023317742A1 (en) | 2022-08-02 | 2025-03-20 | Liminal Biosciences Limited | Substituted pyridone gpr84 antagonists and uses thereof |
| CN120019047A (zh) | 2022-08-02 | 2025-05-16 | 里米诺生物科学有限公司 | 杂芳基甲酰胺和相关gpr84拮抗剂及其用途 |
| CN115745896B (zh) * | 2022-11-18 | 2024-08-06 | 合肥医工医药股份有限公司 | 一种jak2激酶选择性抑制剂及其制备方法和用途 |
| WO2024112894A1 (en) | 2022-11-22 | 2024-05-30 | PIC Therapeutics, Inc. | Eif4e inhibitors and uses thereof |
| WO2024179699A1 (en) * | 2023-03-02 | 2024-09-06 | Bash Biotech Inc. | New compounds and treatment of renal cell carcinoma |
| IL321489A (en) | 2023-06-23 | 2025-08-01 | Kymera Therapeutics Inc | IRAQ joints and their uses |
| WO2025062372A1 (en) | 2023-09-21 | 2025-03-27 | Takeda Pharmaceutical Company Limited | Tyk2 inhibitors for use in the treatment of inflammatory bowel disease |
Family Cites Families (231)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2A (en) * | 1826-12-15 | 1836-07-29 | John Goulding | Mode of manufacturing wool or other fibrous materials |
| US2003199A (en) | 1930-05-31 | 1935-05-28 | Johnson Frank James | Automatic coal stoker |
| US2003149A (en) | 1931-05-22 | 1935-05-28 | Autographic Register Co | Manifolding |
| US2003065A (en) | 1931-06-20 | 1935-05-28 | John R Ditmars | Composition for coating sheets, fibrous stocks, and the like |
| US2004102A (en) | 1932-02-24 | 1935-06-11 | Daniel A Dickey | Hollow steel propeller construction |
| US2004138A (en) | 1932-11-30 | 1935-06-11 | Byers A M Co | Method of making wrought iron pipe |
| US2002165A (en) | 1933-07-08 | 1935-05-21 | Charles A Winslow | Air cleaner |
| US2003187A (en) | 1933-10-02 | 1935-05-28 | Frederick H Shaw | Automobile radio device |
| US2003166A (en) | 1933-10-26 | 1935-05-28 | Zancan Ottavio | Front drive for motor cars |
| US2001051A (en) | 1933-12-01 | 1935-05-14 | Angelina Mariani | Tamperproof meter box with cutout control and fuse drawer for electric meters |
| US2004092A (en) | 1933-12-15 | 1935-06-11 | John L Chaney | Device for indicating the temperature of liquids |
| US2003060A (en) | 1934-04-02 | 1935-05-28 | Ernest L Heckert | Thermostatic controlling device |
| US2667486A (en) | 1951-05-24 | 1954-01-26 | Research Corp | 2,4-diamino pteridine and derivatives |
| IL44058A (en) | 1973-02-02 | 1978-10-31 | Ciba Geigy Ag | 3amino-1,2,4-benzotriazine 1,4-di-noxide derivatives, their preparation and compositions for the control of microorganisms containing them |
| AU535258B2 (en) | 1979-08-31 | 1984-03-08 | Ici Australia Limited | Benzotriazines |
| DE3205638A1 (de) | 1982-02-17 | 1983-08-25 | Hoechst Ag, 6230 Frankfurt | Trisubstituierte pyrimidin-5-carbonsaeuren und deren derivate, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel |
| US4490289A (en) | 1982-09-16 | 1984-12-25 | Hoffmann-La Roche Inc. | Homogeneous human interleukin 2 |
| DE3518887C1 (de) | 1985-05-25 | 1986-09-18 | Ernst Leitz Wetzlar Gmbh, 6330 Wetzlar | Verfahren und Anordnung zur automatischen Bestimmung und Einstellung von Aufnahmeparametern bei einer fotografischen Aufnahmekamera |
| US5616584A (en) | 1986-09-25 | 1997-04-01 | Sri International | 1,2,4-benzotriazine oxides as radiosensitizers and selective cytotoxic agents |
| JPH0741461B2 (ja) | 1987-06-01 | 1995-05-10 | 株式会社日立製作所 | 剪断機 |
| JP2598100B2 (ja) | 1988-08-31 | 1997-04-09 | キヤノン株式会社 | 電子写真感光体 |
| US5214059A (en) | 1989-07-03 | 1993-05-25 | Hoechst-Roussel Pharmaceuticals Incorporated | 2-(aminoaryl) indoles and indolines as topical antiinflammatory agents for the treatment of skin disorders |
| US5776502A (en) | 1989-07-18 | 1998-07-07 | Oncogene Science, Inc. | Methods of transcriptionally modulating gene expression |
| US5665543A (en) | 1989-07-18 | 1997-09-09 | Oncogene Science, Inc. | Method of discovering chemicals capable of functioning as gene expression modulators |
| GB9003553D0 (en) | 1990-02-16 | 1990-04-11 | Ici Plc | Herbicidal compositions |
| JP2839106B2 (ja) | 1990-02-19 | 1998-12-16 | キヤノン株式会社 | 電子写真感光体 |
| JPH03127790U (enExample) | 1990-04-06 | 1991-12-24 | ||
| GB9012592D0 (en) | 1990-06-06 | 1990-07-25 | Smithkline Beecham Intercredit | Compounds |
| FR2665159B1 (fr) | 1990-07-24 | 1992-11-13 | Rhone Poulenc Sante | Nouveaux derives de la pyridine et de la quinoleine, leur preparation et les compositions pharmaceutiques qui les contiennent. |
| MY107955A (en) | 1990-07-27 | 1996-07-15 | Ici Plc | Fungicides. |
| GB9016800D0 (en) | 1990-07-31 | 1990-09-12 | Shell Int Research | Tetrahydropyrimidine derivatives |
| DE4025891A1 (de) | 1990-08-16 | 1992-02-20 | Bayer Ag | Pyrimidyl-substituierte acrylsaeureester |
| AU664827B2 (en) * | 1991-05-03 | 1995-12-07 | Raisio Benecol Ltd. | A substance for lowering high cholesterol level in serum and a method for preparing the same |
| JPH05345780A (ja) | 1991-12-24 | 1993-12-27 | Kumiai Chem Ind Co Ltd | ピリミジンまたはトリアジン誘導体及び除草剤 |
| HUT63941A (en) | 1992-05-15 | 1993-11-29 | Hoechst Ag | Process for producing 4-alkyl-substituted pyrimidine-5-carboxanilide derivatives, and fungicidal compositions comprising same |
| US5438130A (en) | 1993-01-15 | 1995-08-01 | Cambridge Neuroscience, Inc. | Fucosylated guanosine disulfates as excitatory amino acid antagonists |
| DE4338704A1 (de) | 1993-11-12 | 1995-05-18 | Hoechst Ag | Stabilisierte Oligonucleotide und deren Verwendung |
| US5530000A (en) | 1993-12-22 | 1996-06-25 | Ortho Pharmaceutical Corporation | Substituted pyrimidinylaminothiazole derivatives useful as platelet aggreggation inhibitors |
| GB9506466D0 (en) | 1994-08-26 | 1995-05-17 | Prolifix Ltd | Cell cycle regulated repressor and dna element |
| US5597826A (en) | 1994-09-14 | 1997-01-28 | Pfizer Inc. | Compositions containing sertraline and a 5-HT1D receptor agonist or antagonist |
| DE19502912A1 (de) | 1995-01-31 | 1996-08-01 | Hoechst Ag | G-Cap Stabilisierte Oligonucleotide |
| US6326487B1 (en) | 1995-06-05 | 2001-12-04 | Aventis Pharma Deutschland Gmbh | 3 modified oligonucleotide derivatives |
| EP0850228A1 (en) | 1995-09-01 | 1998-07-01 | Signal Pharmaceuticals, Inc. | Pyrimidine carboxamides and related compounds and methods for treating inflammatory conditions |
| GB9523675D0 (en) | 1995-11-20 | 1996-01-24 | Celltech Therapeutics Ltd | Chemical compounds |
| TR199801255T2 (xx) | 1995-12-29 | 1998-10-21 | Smithkline Beecham Corporation | Vitronektin resept�r antagonistleri. |
| JPH09274290A (ja) | 1996-02-07 | 1997-10-21 | Fuji Photo Film Co Ltd | ハロゲン化銀写真感光材料用の現像液および処理方法 |
| WO1997030707A1 (en) | 1996-02-23 | 1997-08-28 | Eli Lilly And Company | NON-PEPTIDYL VASOPRESSIN V1a ANTAGONISTS |
| DE59707681D1 (de) | 1996-10-28 | 2002-08-14 | Rolic Ag Zug | Vernetzbare, photoaktive Silanderivate |
| WO1998022588A2 (en) | 1996-11-20 | 1998-05-28 | Introgen Therapeutics, Inc. | An improved method for the production and purification of adenoviral vectors |
| JP3734903B2 (ja) | 1996-11-21 | 2006-01-11 | 富士写真フイルム株式会社 | 現像処理方法 |
| JPH10153838A (ja) | 1996-11-22 | 1998-06-09 | Fuji Photo Film Co Ltd | ハロゲン化銀写真感光材料の処理方法 |
| JP3720931B2 (ja) | 1996-11-26 | 2005-11-30 | 富士写真フイルム株式会社 | ハロゲン化銀写真感光材料の処理方法 |
| US5935383A (en) | 1996-12-04 | 1999-08-10 | Kimberly-Clark Worldwide, Inc. | Method for improved wet strength paper |
| BR9713842A (pt) | 1996-12-04 | 2000-10-31 | Kimberly Clark Co | Método para fabricar papel com resistência úmida |
| EP0946528B1 (en) | 1996-12-23 | 2003-04-09 | Bristol-Myers Squibb Pharma Company | OXYGEN OR SULFUR CONTAINING 5-MEMBERED HETEROAROMATICS AS FACTOR Xa INHIBITORS |
| JPH10207019A (ja) | 1997-01-22 | 1998-08-07 | Fuji Photo Film Co Ltd | ハロゲン化銀写真感光材料の処理方法 |
| JPH10213820A (ja) | 1997-01-31 | 1998-08-11 | Canon Inc | 液晶素子及び液晶装置 |
| DE59807348D1 (de) | 1997-02-05 | 2003-04-10 | Rolic Ag Zug | Photovernetzbare Silanderivate |
| GB9705361D0 (en) * | 1997-03-14 | 1997-04-30 | Celltech Therapeutics Ltd | Chemical compounds |
| JPH10260512A (ja) | 1997-03-19 | 1998-09-29 | Fuji Photo Film Co Ltd | ハロゲン化銀感光材料の処理方法 |
| JPH10310583A (ja) | 1997-05-09 | 1998-11-24 | Mitsubishi Chem Corp | ピリドンアゾ系化合物、感熱転写用色素およびそれを使用した感熱転写材料 |
| US6070126A (en) | 1997-06-13 | 2000-05-30 | William J. Kokolus | Immunobiologically-active linear peptides and method of identification |
| TW436485B (en) | 1997-08-01 | 2001-05-28 | American Cyanamid Co | Substituted quinazoline derivatives |
| US6635626B1 (en) | 1997-08-25 | 2003-10-21 | Bristol-Myers Squibb Co. | Imidazoquinoxaline protein tyrosine kinase inhibitors |
| US6022884A (en) | 1997-11-07 | 2000-02-08 | Amgen Inc. | Substituted pyridine compounds and methods of use |
| ATE401312T1 (de) * | 1997-12-15 | 2008-08-15 | Astellas Pharma Inc | Pyrimidin-5-carboxamid-derivate |
| BR9813835A (pt) | 1997-12-22 | 2000-10-10 | Du Pont Pharm Co | Composto, composição farmacêutica e método de tratamento ou prevenção de uma desordem tromboembólica |
| CA2321153A1 (en) | 1998-02-17 | 1999-08-19 | Timothy D. Cushing | Anti-viral pyrimidine derivatives |
| DE69943247D1 (de) | 1998-03-27 | 2011-04-14 | Janssen Pharmaceutica Nv | HIV hemmende Pyrimidin Derivate |
| US6685938B1 (en) | 1998-05-29 | 2004-02-03 | The Scripps Research Institute | Methods and compositions useful for modulation of angiogenesis and vascular permeability using SRC or Yes tyrosine kinases |
| US6136971A (en) | 1998-07-17 | 2000-10-24 | Roche Colorado Corporation | Preparation of sulfonamides |
| US6378526B1 (en) | 1998-08-03 | 2002-04-30 | Insite Vision, Incorporated | Methods of ophthalmic administration |
| AU5438299A (en) * | 1998-08-29 | 2000-03-21 | Astrazeneca Ab | Pyrimidine compounds |
| CN1165532C (zh) | 1998-09-29 | 2004-09-08 | 惠氏控股有限公司 | 作为蛋白质酪氨酸激酶抑制剂的取代的3-氰基喹啉 |
| US6288082B1 (en) | 1998-09-29 | 2001-09-11 | American Cyanamid Company | Substituted 3-cyanoquinolines |
| PT2253620E (pt) | 1998-09-29 | 2014-04-15 | Wyeth Holdings Llc | 3-cianoquinolinas substituídas como inibidores de proteínas tirosinas quinases |
| US6297258B1 (en) | 1998-09-29 | 2001-10-02 | American Cyanamid Company | Substituted 3-cyanoquinolines |
| EP1058549A4 (en) | 1998-12-23 | 2003-11-12 | Bristol Myers Squibb Pharma Co | FACTOR Xa OR THROMBIN INHIBITORS |
| GB9828511D0 (en) * | 1998-12-24 | 1999-02-17 | Zeneca Ltd | Chemical compounds |
| CA2362401A1 (en) | 1999-02-04 | 2000-08-10 | Paul Fleming | G-protein coupled heptahelical receptor binding compounds and methods of use thereof |
| ID30460A (id) | 1999-04-15 | 2001-12-06 | Bristol Myers Squibb Co | Inhibitor-inhibitor protein siklik tirosin kinase |
| ATE264328T1 (de) | 1999-04-21 | 2004-04-15 | Wyeth Corp | Substituierte 3-cyano-(1.7), (1.5) und (1.8)naphthyridininhibitoren von tyrosin kinasen |
| AU5020400A (en) | 1999-05-20 | 2000-12-12 | E.I. Du Pont De Nemours And Company | Heteroaryloxypyrimidine insecticides and acaricides |
| CN1372548A (zh) | 1999-07-01 | 2002-10-02 | 味之素株式会社 | 杂环化合物及其医药用途 |
| WO2001007027A2 (en) | 1999-07-22 | 2001-02-01 | Vertex Pharmaceuticals Incorporated | Pyrimidine derivatives for the treatment of viral diseases |
| AU6016000A (en) | 1999-07-23 | 2001-02-13 | Shionogi & Co., Ltd. | Tricyclic compounds and drug compositions containing the same |
| KR20020012309A (ko) | 1999-07-23 | 2002-02-15 | 시오노 요시히코 | Th2 분화 억제제 |
| IL147913A0 (en) | 1999-08-12 | 2002-08-14 | American Cyanamid Co | Nsaid and efgr kinase inhibitor containing composition for the treatment or inhibition of colonic polyps and colorectal cancer |
| US6093838A (en) | 1999-08-16 | 2000-07-25 | Allergan Sales, Inc. | Amines substituted with a dihydro-benzofuranyl or with a dihydro-isobenzofuranyl group, an aryl or heteroaryl group and an alkyl group, having retinoid-like biological activity |
| US6127382A (en) | 1999-08-16 | 2000-10-03 | Allergan Sales, Inc. | Amines substituted with a tetrahydroquinolinyl group an aryl or heteroaryl group and an alkyl group, having retinoid-like biological activity |
| CN1390215A (zh) | 1999-09-10 | 2003-01-08 | 麦克公司 | 酪氨酸激酶抑制剂 |
| GB9922171D0 (en) | 1999-09-21 | 1999-11-17 | Zeneca Ltd | Chemical compounds |
| JP2001089412A (ja) | 1999-09-22 | 2001-04-03 | Otsuka Pharmaceut Co Ltd | ベンゼン誘導体またはその医薬的に許容される塩 |
| US6506769B2 (en) | 1999-10-06 | 2003-01-14 | Boehringer Ingelheim Pharmaceuticals, Inc. | Heterocyclic compounds useful as inhibitors of tyrosine kinases |
| AU7683500A (en) | 1999-10-12 | 2001-04-23 | Takeda Chemical Industries Ltd. | Pyrimidine-5-carboxamide compounds, process for producing the same and use thereof |
| GB9924092D0 (en) * | 1999-10-13 | 1999-12-15 | Zeneca Ltd | Pyrimidine derivatives |
| EP1226123A1 (en) | 1999-11-03 | 2002-07-31 | Du Pont Pharmaceuticals Company | Cyano compounds as factor xa inhibitors |
| GB9929988D0 (en) | 1999-12-17 | 2000-02-09 | Celltech Therapeutics Ltd | Chemical compounds |
| CA2396579A1 (en) | 1999-12-29 | 2001-07-05 | Wyeth | Tricyclic protein kinase inhibitors |
| US6638929B2 (en) | 1999-12-29 | 2003-10-28 | Wyeth | Tricyclic protein kinase inhibitors |
| EP1294709A2 (en) | 2000-01-28 | 2003-03-26 | AstraZeneca AB | Quinoline derivatives and their use as aurora 2 kinase inhibitors |
| US6153752A (en) | 2000-01-28 | 2000-11-28 | Creanova, Inc. | Process for preparing heterocycles |
| US20020165244A1 (en) | 2000-01-31 | 2002-11-07 | Yuhong Zhou | Mucin synthesis inhibitors |
| JP2003532635A (ja) | 2000-02-17 | 2003-11-05 | アムジエン・インコーポレーテツド | キナーゼ阻害薬 |
| EP1261327B1 (en) | 2000-02-25 | 2005-04-27 | F.Hoffmann-La Roche Ag | Adenosine receptor modulators |
| CA2397661C (en) | 2000-03-01 | 2012-01-03 | Janssen Pharmaceutica N.V. | 2,4-disubstituted thiazolyl derivatives |
| GB0004890D0 (en) | 2000-03-01 | 2000-04-19 | Astrazeneca Uk Ltd | Chemical compounds |
| GB0004887D0 (en) * | 2000-03-01 | 2000-04-19 | Astrazeneca Uk Ltd | Chemical compounds |
| GB0004888D0 (en) | 2000-03-01 | 2000-04-19 | Astrazeneca Uk Ltd | Chemical compounds |
| US6605615B2 (en) | 2000-03-01 | 2003-08-12 | Tularik Inc. | Hydrazones and analogs as cholesterol lowering agents |
| JP2001247411A (ja) | 2000-03-09 | 2001-09-11 | Tomono Agrica Co Ltd | 有害生物防除剤 |
| KR100817423B1 (ko) | 2000-03-13 | 2008-03-27 | 와이어쓰 홀딩스 코포레이션 | 시아노퀴놀린을 포함하는 결장 폴립의 치료 또는 억제를 위한 약제학적 조성물 |
| US6613917B1 (en) | 2000-03-23 | 2003-09-02 | Allergan, Inc. | Amines substituted with a dihydronaphthalenyl, chromenyl, or thiochromenyl group, an aryl or heteroaryl group and an alkyl group, having retinoid-like biological activity |
| US6608048B2 (en) | 2000-03-28 | 2003-08-19 | Wyeth Holdings | Tricyclic protein kinase inhibitors |
| AR028261A1 (es) | 2000-03-28 | 2003-04-30 | Wyeth Corp | Inhibidores triciclicos de la proteina quinasa |
| WO2001074331A1 (en) | 2000-04-04 | 2001-10-11 | Shionogi & Co., Ltd. | Oily compositions containing highly fat-soluble drugs |
| AU2001244610A1 (en) | 2000-04-05 | 2001-10-23 | Shionogi And Co., Ltd. | Oil-in-water microemulsions containing tricyclic compounds or preconcentrates thereof |
| FR2808163B1 (fr) * | 2000-04-19 | 2002-11-08 | Celes | Dispositif de chauffage par induction a flux transverse a circuit magnetique de largeur variable |
| US6471968B1 (en) | 2000-05-12 | 2002-10-29 | Regents Of The University Of Michigan | Multifunctional nanodevice platform |
| DE10024622A1 (de) | 2000-05-18 | 2001-11-22 | Piesteritz Stickstoff | N-(2-Pyrimidinyl)(thio)phosphorsäuretriamide, Verfahren zu ihrer Herstellung und deren Verwendung als Mittel zur Regulierung bzw. Hemmung der enzymatischen Harnstoff-Hydrolyse |
| DE60114518T2 (de) | 2000-07-06 | 2006-08-10 | Fuji Photo Film Co. Ltd., Minamiashigara | Flüssigkristallzusammensetzung, die Flüssigkristallmoleküle und Ausrichtungsmittel enthält |
| MXPA03001306A (es) | 2000-08-11 | 2003-10-15 | Boehringer Ingelheim Pharma | Compuestos heterociclicos utiles como inhibidores de las quinasas de tirosina. |
| ATE346064T1 (de) | 2000-09-15 | 2006-12-15 | Vertex Pharma | Pyrazolverbindungen als protein-kinasehemmer |
| AU2002213467A1 (en) | 2000-10-11 | 2002-04-22 | Chemocentryx, Inc. | Modulation of ccr4 function |
| JP2004514718A (ja) | 2000-11-02 | 2004-05-20 | アストラゼネカ アクチボラグ | 抗癌剤としての置換キノリン類 |
| US7253184B2 (en) | 2000-11-02 | 2007-08-07 | Astrazeneca Ab | 4-Substituted quinolines as antitumor agents |
| WO2002042272A2 (en) | 2000-11-20 | 2002-05-30 | Pharmacia Corporation | Substituted polycyclic aryl and heteroaryl pyridines useful for selective inhibition of the coagulation cascade |
| WO2002053101A2 (en) | 2000-12-29 | 2002-07-11 | Alteon, Inc. | Method for treating fibrotic diseases or other indications |
| EP1353674A1 (en) | 2000-12-29 | 2003-10-22 | Alteon, Inc. | Method for treating glaucoma ivb |
| JP2002221770A (ja) | 2001-01-24 | 2002-08-09 | Fuji Photo Film Co Ltd | ハロゲン化銀写真感光材料およびその処理方法 |
| US20030130264A1 (en) | 2001-02-16 | 2003-07-10 | Tularik Inc. | Methods of using pyrimidine-based antiviral agents |
| PT1379520E (pt) | 2001-02-23 | 2006-08-31 | Merck & Co Inc | Antagonistas (nao-aril)-heterociclicos n-substituidos de nmda/nr2b |
| AU2002247402A1 (en) | 2001-03-23 | 2002-10-08 | Chugai Seiyaku Kabushiki Kaisha | Flt-1 ligands and their uses in the treatment of diseases regulatable by angiogenesis |
| DE60214701T2 (de) | 2001-04-13 | 2007-09-13 | Vertex Pharmaceuticals Inc., Cambridge | Inhibitoren von c-jun-n-terminalen-kinasen (jnk) und anderen proteinkinasen |
| NZ528961A (en) * | 2001-04-20 | 2005-04-29 | Bayer Cropscience Ag | Novel insecticidal azoles |
| JP2004532856A (ja) | 2001-04-30 | 2004-10-28 | 藤沢薬品工業株式会社 | アポリポタンパク質b阻害剤としてのビアリールカルボキサミド化合物 |
| EP1392300A1 (en) | 2001-05-11 | 2004-03-03 | Vertex Pharmaceuticals Incorporated | 2,5-disubstituted pyridine, pyrimidine, pyridazine and 1, 2, 4-triazine derivatives for use as p38 inhibitors |
| WO2002094766A1 (en) | 2001-05-18 | 2002-11-28 | Nihon Nohyaku Co., Ltd. | Phthalamide derivative, agricultural or horticultural insecticide, and use thereof |
| AU2002314252A1 (en) | 2001-05-28 | 2002-12-09 | Aventis Pharma S.A. | Chemical derivatives and the use thereof as an anti-telomerase agent |
| HRP20031081A2 (en) | 2001-05-29 | 2005-10-31 | Schering Aktiengesellschaft | Cdk inhibiting pyrimidines, production thereof and their use as medicaments |
| US7025987B2 (en) | 2001-05-30 | 2006-04-11 | The Scripps Research Institute | Delivery system for nucleic acids |
| ATE337312T1 (de) | 2001-07-03 | 2006-09-15 | Vertex Pharma | Isoxazolyl-pyrimidines als inhibitoren von src- und lck-protein-kinasen |
| US6861529B2 (en) | 2001-07-06 | 2005-03-01 | Pfizer Inc | Cycloalkypyrrole-3-carboxylic acid derivatives and heterocycloalkylpyrrole-3-carboxylic acid derivatives |
| JO3429B1 (ar) | 2001-08-13 | 2019-10-20 | Janssen Pharmaceutica Nv | مشتقات برميدينات مثبطة فيروس الايدز |
| KR20100107509A (ko) | 2001-09-14 | 2010-10-05 | 9222-9129 퀘벡 인코포레이티드 | 히스톤 데아세틸라아제의 억제제 |
| WO2003030909A1 (en) | 2001-09-25 | 2003-04-17 | Bayer Pharmaceuticals Corporation | 2- and 4-aminopyrimidines n-substtituded by a bicyclic ring for use as kinase inhibitors in the treatment of cancer |
| DE10150610A1 (de) | 2001-10-12 | 2003-04-30 | Clariant Gmbh | Verfahren zur metallorganischen Herstellung organischer Zwischenprodukte über Amidbasen |
| DE10150614A1 (de) | 2001-10-12 | 2003-04-30 | Clariant Gmbh | Verfahren zur metallorganischen Herstellung organischer Zwischenprodukte über Halogen-Metall-Austauschreaktionen |
| DE10150615A1 (de) | 2001-10-12 | 2003-04-30 | Clariant Gmbh | Verfahren zur metallorganischen Herstellung organischer Zwischenprodukte |
| EP1453516A2 (de) * | 2001-10-17 | 2004-09-08 | Boehringer Ingelheim Pharma GmbH & Co.KG | 5-substituierte 4-amino-2-phenylamino-pyrimdinderivate und ihre verwendung als beta-amyloid modulatoren |
| IL161662A0 (en) | 2001-11-01 | 2004-09-27 | Janssen Pharmaceutica Nv | Heteroaryl amines as glycogen synthase kinase 3 beta inhibitors (gsk3 inhibitors) |
| HUP0402330A3 (en) | 2001-11-01 | 2010-03-29 | Janssen Pharmaceutica Nv | Amide derivatives as glycogen synthase kinase 3-beta inhibitors, process for producing them, pharmaceutical compositions containing them and use thereof |
| AU2002359489B2 (en) | 2001-11-27 | 2008-10-30 | Wyeth Holdings Corporation | 3-cyanoquinolines as inhibitors of EGF-R and Her2 kinases |
| AU2002344567A1 (en) | 2001-11-28 | 2003-06-10 | Daiso Co., Ltd. | Heterocyclic amide compounds as apolipoprotein b inhibitors |
| US20030187026A1 (en) | 2001-12-13 | 2003-10-02 | Qun Li | Kinase inhibitors |
| IL162838A0 (en) | 2002-01-04 | 2005-11-20 | Univ Rockefeller | Compositions and methods for prevention and treatment peptide-of amyloid- related disorders |
| US20030166932A1 (en) | 2002-01-04 | 2003-09-04 | Beard Richard L. | Amines substituted with a dihydronaphthalenyl, chromenyl, or thiochromenyl group, an aryl or heteroaryl group and an alkyl group, having retinoid-like biological activity |
| TWI329105B (en) * | 2002-02-01 | 2010-08-21 | Rigel Pharmaceuticals Inc | 2,4-pyrimidinediamine compounds and their uses |
| ATE470656T1 (de) | 2002-02-05 | 2010-06-15 | Wyeth Llc | Verfahren zur herstellung von n-acyl-2-amino-4- alkoxy-5-nitrobenzoesäuren |
| MXPA04008458A (es) | 2002-03-01 | 2004-12-06 | Smithkline Beecham Corp | Diamino pirimidinas y su uso como inhibidores de angiogenesis. |
| GB0206215D0 (en) | 2002-03-15 | 2002-05-01 | Novartis Ag | Organic compounds |
| AU2003231231A1 (en) | 2002-05-06 | 2003-11-11 | Bayer Pharmaceuticals Corporation | Pyridinyl amino pyrimidine derivatives useful for treating hyper-proliferative disorders |
| AR037647A1 (es) | 2002-05-29 | 2004-12-01 | Novartis Ag | Derivados de diarilurea utiles para el tratamiento de enfermedades dependientes de la cinasa de proteina |
| MY141867A (en) | 2002-06-20 | 2010-07-16 | Vertex Pharma | Substituted pyrimidines useful as protein kinase inhibitors |
| JP4570955B2 (ja) | 2002-07-09 | 2010-10-27 | バーテクス ファーマスーティカルズ インコーポレイテッド | プロテインキナーゼ阻害活性を持つイミダゾール類 |
| RS51752B (sr) * | 2002-07-29 | 2011-12-31 | Rigel Pharmaceuticals | Metode tretiranja i prevencije autoimunih oboljenja jedinjenjima 2,4-pirimidindiamina |
| PT1525200E (pt) | 2002-08-02 | 2008-01-10 | Ab Science | 2-(3-aminoaril)amino-4-aril-tiazóis para o tratamento de doenças |
| US7304071B2 (en) | 2002-08-14 | 2007-12-04 | Vertex Pharmaceuticals Incorporated | Protein kinase inhibitors and uses thereof |
| UY27939A1 (es) | 2002-08-21 | 2004-03-31 | Glaxo Group Ltd | Compuestos |
| DE10240261A1 (de) | 2002-08-31 | 2004-03-11 | Clariant Gmbh | Verfahren zur metallorganischen Herstellung organischer Zwischenprodukte über Halogen-Metall-Austauschreaktionen |
| DE10240262A1 (de) | 2002-08-31 | 2004-03-11 | Clariant Gmbh | Verfahren zur metallorganischen Herstellung organischer Zwischenprodukte über Aryllithium-Basen |
| CA2500727A1 (en) | 2002-10-03 | 2004-04-15 | Targegen, Inc. | Vasculostatic agents and methods of use thereof |
| US20050282814A1 (en) | 2002-10-03 | 2005-12-22 | Targegen, Inc. | Vasculostatic agents and methods of use thereof |
| CA2500368A1 (en) | 2002-10-04 | 2004-04-22 | Caritas St. Elizabeth's Medical Center Of Boston, Inc. | Inhibition of src for treatment of reperfusion injury related to revascularization |
| WO2004037176A2 (en) | 2002-10-21 | 2004-05-06 | Bristol-Myers Squibb Company | Quinazolinones and derivatives thereof as factor xa inhibitors |
| WO2004037814A1 (en) | 2002-10-25 | 2004-05-06 | Vertex Pharmaceuticals Incorporated | Indazolinone compositions useful as kinase inhibitors |
| US7452911B2 (en) | 2002-10-31 | 2008-11-18 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Alkyne compounds with MCH antagonistic activity and medicaments comprising these compounds |
| DE10250708A1 (de) | 2002-10-31 | 2004-05-19 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Alkin-Verbindungen mit MCH-antagonistischer Wirkung und diese Verbindungen enthaltende Arzneimittel |
| US7129351B2 (en) * | 2002-11-04 | 2006-10-31 | Hoffmann-La Roche Inc. | Pyrimido compounds having antiproliferative activity |
| EP1562938B1 (en) | 2002-11-04 | 2007-08-29 | Vertex Pharmaceuticals Incorporated | Heteroaryl-pyrimidine derivatives as jak inhibitors |
| US20050101576A1 (en) | 2003-11-06 | 2005-05-12 | Novacea, Inc. | Methods of using vitamin D compounds in the treatment of myelodysplastic syndromes |
| AU2003280188A1 (en) | 2002-12-06 | 2004-06-30 | Warner-Lambert Company Llc | Benzoxazin-3-ones and derivatives thereof as inhibitors of pi3k |
| WO2004054186A1 (ja) | 2002-12-12 | 2004-06-24 | Fujitsu Limited | データ中継装置、連想メモリデバイス、および連想メモリデバイス利用情報検索方法 |
| UA80767C2 (en) | 2002-12-20 | 2007-10-25 | Pfizer Prod Inc | Pyrimidine derivatives for the treatment of abnormal cell growth |
| CA2507699A1 (en) | 2002-12-20 | 2004-07-15 | Pharmacia Corporation | Heteroarylalkanoic acids as integrin receptor antagonists |
| WO2004060376A1 (en) | 2002-12-20 | 2004-07-22 | Pharmacia Corpration | The r-isomer of beta amino acid compounds as integrin receptor antagonists derivatives |
| EP1575966B1 (en) | 2002-12-24 | 2008-10-29 | AstraZeneca AB | Therapeutic quinazoline derivatives |
| US7144911B2 (en) | 2002-12-31 | 2006-12-05 | Deciphera Pharmaceuticals Llc | Anti-inflammatory medicaments |
| US20070021449A1 (en) | 2003-02-07 | 2007-01-25 | Jan Heeres | Pyrimidine derivatives for the prevention of hiv infection |
| KR20050105190A (ko) | 2003-02-07 | 2005-11-03 | 얀센 파마슈티카 엔.브이. | Hiv를 저해하는 1,2,4-트리아진 |
| WO2004071426A2 (en) | 2003-02-11 | 2004-08-26 | Kemia Inc. | Compounds for the treatment of viral infection |
| CL2004000306A1 (es) | 2003-02-20 | 2005-04-08 | Tibotec Pharm Ltd | Compuestos derivados de pirimidina sustituidas con indano; proceso para su preparacion; composicion farmaceutica que lo comprende; combinacion farmaceutica; y su uso para el tratamiento o profilaxis de una enfermedad infecciosa. |
| GB0305929D0 (en) | 2003-03-14 | 2003-04-23 | Novartis Ag | Organic compounds |
| ES2634840T5 (es) | 2003-04-24 | 2022-12-22 | Coopervision Int Ltd | Lentes de contacto de hidrogel y sistemas de envase y procedimientos de producción de los mismos |
| HRP20130602T1 (en) * | 2003-07-30 | 2013-07-31 | Rigel Pharmaceuticals, Inc. | 2,4-pyrimidinediamine compounds for use in the treatment or prevention of autoimmune diseases |
| RU2395500C2 (ru) * | 2003-08-15 | 2010-07-27 | Новартис Аг | 2,4-пиримидиндиамины, применяемые в лечении неопластических болезней, воспалительных и иммунных расстройств |
| GB0321710D0 (en) | 2003-09-16 | 2003-10-15 | Novartis Ag | Organic compounds |
| AU2004272288B2 (en) | 2003-09-18 | 2008-11-13 | Novartis Ag | 2,4-di (phenylamino) pyrimidines useful in the treatment of proliferative disorders |
| NZ551027A (en) * | 2004-04-08 | 2011-01-28 | Targegen Inc | Benzotriazine inhibitors of kinases |
| MX2007002208A (es) | 2004-08-25 | 2007-05-08 | Targegen Inc | Compuestos hetrociclicos y metodos de uso. |
| US7210697B2 (en) | 2004-12-16 | 2007-05-01 | Tricam International, Inc. | Convertible handle |
| US8211929B2 (en) * | 2004-12-30 | 2012-07-03 | Exelixis, Inc. | Pyrimidine derivatives as kinase modulators and method of use |
| GB0501999D0 (en) | 2005-02-01 | 2005-03-09 | Sentinel Oncology Ltd | Pharmaceutical compounds |
| CN101155799A (zh) * | 2005-03-16 | 2008-04-02 | 塔格根公司 | 嘧啶化合物和使用方法 |
| US7389455B2 (en) * | 2005-05-16 | 2008-06-17 | Texas Instruments Incorporated | Register file initialization to prevent unknown outputs during test |
| US20070032493A1 (en) | 2005-05-26 | 2007-02-08 | Synta Pharmaceuticals Corp. | Method for treating B cell regulated autoimmune disorders |
| WO2006128129A2 (en) | 2005-05-26 | 2006-11-30 | Synta Pharmaceuticals Corp. | Method for treating cancer |
| CA2608367C (en) | 2005-06-08 | 2014-08-19 | Rigel Pharmaceuticals, Inc. | Compositions and methods for inhibition of the jak pathway |
| CA2611720A1 (en) | 2005-06-08 | 2006-12-14 | Targegen, Inc. | Methods and compositions for the treatment of ocular disorders |
| WO2006137658A1 (en) | 2005-06-20 | 2006-12-28 | Dongbu Hitek Co., Ltd. | New substituted 1,3-thiazole derivatives or pharmaceutically acceptable salts thereof having immunosuppression and inflammation inhibitory acitivity, intermediate compounds or pharmaceutically acceptable salts thereof, a process for the preparation thereof, and pharmaceutical composition comprising the same |
| WO2007008541A2 (en) * | 2005-07-08 | 2007-01-18 | Kalypsys, Inc. | Cellular cholesterol absorption modifiers |
| US7754717B2 (en) | 2005-08-15 | 2010-07-13 | Amgen Inc. | Bis-aryl amide compounds and methods of use |
| WO2007038215A1 (en) | 2005-09-22 | 2007-04-05 | Incyte Corporation | Tetracyclic inhibitors of janus kinases |
| US20070072682A1 (en) | 2005-09-29 | 2007-03-29 | Crawford James T Iii | Head to head electronic poker game assembly and method of operation |
| MX362412B (es) * | 2005-11-01 | 2019-01-15 | Targegen Inc | Inhibidores de biaril meta-pirimidina de cinasas. |
| US8133900B2 (en) | 2005-11-01 | 2012-03-13 | Targegen, Inc. | Use of bi-aryl meta-pyrimidine inhibitors of kinases |
| WO2007056023A2 (en) | 2005-11-02 | 2007-05-18 | Targegen, Inc. | Thiazole inhibitors targeting resistant kinase mutations |
| WO2007053776A1 (en) | 2005-11-03 | 2007-05-10 | Sgx Pharmaceuticals, Inc. | Pyrimidinyl-thiophene kinase modulators |
| PH12012501003B1 (en) | 2005-11-16 | 2018-04-06 | Cti Biopharma Corp | Oxygen linked pyrimidine derivatives |
| ATE525374T1 (de) | 2005-12-13 | 2011-10-15 | Incyte Corp | Heteroarylsubstituierte pyrroloä2,3-büpyridine und pyrroloä2,3-büpyrimidine als januskinaseinhibitoren |
| ES2622493T3 (es) * | 2006-02-24 | 2017-07-06 | Rigel Pharmaceuticals, Inc. | Composiciones y métodos para la inhibición de la ruta de JAK |
| US7691858B2 (en) | 2006-04-25 | 2010-04-06 | Targegen, Inc. | Kinase inhibitors and methods of use thereof |
| WO2008008234A1 (en) * | 2006-07-07 | 2008-01-17 | Targegen, Inc. | 2-amino-5-substituted pyrimidine inhibitors |
| US20080021013A1 (en) | 2006-07-21 | 2008-01-24 | Cephalon, Inc. | JAK inhibitors for treatment of myeloproliferative disorders |
| WO2008009458A1 (en) | 2006-07-21 | 2008-01-24 | Novartis Ag | 2, 4 -di (arylaminio) -pyrimidine-5-carboxamide compounds as jak kinases inhibitors |
| ES2467665T5 (es) | 2007-06-13 | 2022-11-03 | Incyte Holdings Corp | Sales del inhibidor de cinasas Janus (R)-3-(4-(7H-pirrolo[2,3-d]pirimidin-4-il)-1H-pirazol-1-il)-3-ciclopentilpropanonitrilo |
| WO2009046416A1 (en) | 2007-10-05 | 2009-04-09 | Targegen Inc. | Anilinopyrimidines as jak kinase inhibitors |
| US20100016218A1 (en) | 2008-07-14 | 2010-01-21 | Otonomy, Inc. | Controlled-release apoptosis modulating compositions and methods for the treatment of otic disorders |
| US20110269721A1 (en) | 2008-08-05 | 2011-11-03 | Targegen, Inc. | Methods of treating thalassemia |
| HRP20150413T8 (xx) | 2008-12-11 | 2015-08-14 | Cti Biopharma Corp. | 11-(2-pirolidin-1-il-etoksi)-14,19-dioksa-5,7,26-triaza-tetraciklo[19.31.1(2,6).1(8,12)]heptakoza-1(25),2(26),3,5,8,10,12(27),16,21,23-dekaen maleatna sol |
| US20100278921A1 (en) | 2009-04-30 | 2010-11-04 | Fischer Cristina M | Solid oral formulation of abt-263 |
-
2006
- 2006-10-26 MX MX2010010772A patent/MX362412B/es unknown
- 2006-10-26 DK DK06836583.2T patent/DK1951684T3/en active
- 2006-10-26 EP EP06836583.2A patent/EP1951684B1/en active Active
- 2006-10-26 LT LTEP06836583.2T patent/LT1951684T/lt unknown
- 2006-10-26 MY MYPI20081381A patent/MY167260A/en unknown
- 2006-10-26 RU RU2012103851/04A patent/RU2597364C2/ru active
- 2006-10-26 CN CN201310043377.0A patent/CN103626742B/zh active Active
- 2006-10-26 ES ES06836583.2T patent/ES2595636T3/es active Active
- 2006-10-26 KR KR1020087013115A patent/KR101494468B1/ko active Active
- 2006-10-26 AU AU2006309013A patent/AU2006309013B2/en active Active
- 2006-10-26 HU HUE06836583A patent/HUE028987T2/en unknown
- 2006-10-26 WO PCT/US2006/042044 patent/WO2007053452A1/en not_active Ceased
- 2006-10-26 NZ NZ592990A patent/NZ592990A/xx unknown
- 2006-10-26 PT PT68365832T patent/PT1951684T/pt unknown
- 2006-10-26 BR BRPI0618179-1A patent/BRPI0618179A2/pt not_active Application Discontinuation
- 2006-10-26 KR KR1020137021980A patent/KR101467723B1/ko active Active
- 2006-10-26 PL PL06836583T patent/PL1951684T3/pl unknown
- 2006-10-26 BR BR122021011788-8A patent/BR122021011788B1/pt active IP Right Grant
- 2006-10-26 RU RU2012103850/04A patent/RU2589878C2/ru active
- 2006-10-26 NZ NZ567851A patent/NZ567851A/en unknown
- 2006-10-26 MX MX2018008723A patent/MX391408B/es unknown
- 2006-10-26 CA CA2628283A patent/CA2628283C/en not_active Expired - Fee Related
- 2006-10-26 US US11/588,638 patent/US7528143B2/en active Active
- 2006-10-26 BR BR122021011787-0A patent/BR122021011787B1/pt active IP Right Grant
- 2006-10-26 JP JP2008538935A patent/JP5191391B2/ja active Active
- 2006-11-01 TW TW095140348A patent/TWI444368B/zh active
-
2007
- 2007-04-26 US US11/796,717 patent/US7825246B2/en active Active
-
2008
- 2008-04-30 IL IL191167A patent/IL191167A/en active IP Right Grant
- 2008-05-30 NO NO20082447A patent/NO342221B1/no active Protection Beyond IP Right Term
- 2008-10-17 US US12/253,374 patent/US8138199B2/en active Active
-
2012
- 2012-11-26 JP JP2012257150A patent/JP5814903B2/ja active Active
-
2016
- 2016-10-12 CY CY20161101021T patent/CY1118330T1/el unknown
-
2021
- 2021-05-12 FI FIC20210010C patent/FIC20210010I1/fi unknown
- 2021-05-17 NL NL301104C patent/NL301104I2/nl unknown
- 2021-05-17 CY CY2021013C patent/CY2021013I2/el unknown
- 2021-05-18 HU HUS2100020C patent/HUS2100020I1/hu unknown
- 2021-05-21 LT LTPA2021509C patent/LTC1951684I2/lt unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| BRPI0618179A2 (pt) | inibidores de biaril meta pirimidina de cinases | |
| US8133900B2 (en) | Use of bi-aryl meta-pyrimidine inhibitors of kinases | |
| US8604042B2 (en) | Bi-aryl meta-pyrimidine inhibitors of kinases | |
| CN101155799A (zh) | 嘧啶化合物和使用方法 | |
| CN101370792B (zh) | 激酶的联-芳基间-嘧啶抑制剂 | |
| WO2007056075A2 (en) | Six membered heteroaromatic inhibitors targeting resistant kinase mutations | |
| AU2012230091B2 (en) | Bi-aryl meta-pyrimidine inhibitors of kinases | |
| HK1121148B (en) | Bi-aryl meta-pyrimidine inhibitors of kinases | |
| MX2008005810A (en) | Bi-aryl meta-pyrimidine inhibitors of kinases | |
| HK1119165A (zh) | 嘧啶化合物和使用方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B06F | Objections, documents and/or translations needed after an examination request according [chapter 6.6 patent gazette] | ||
| B06T | Formal requirements before examination [chapter 6.20 patent gazette] | ||
| B07D | Technical examination (opinion) related to article 229 of industrial property law [chapter 7.4 patent gazette] |
Free format text: DE ACORDO COM O ARTIGO 229-C DA LEI NO 10196/2001, QUE MODIFICOU A LEI NO 9279/96, A CONCESSAO DA PATENTE ESTA CONDICIONADA A ANUENCIA PREVIA DA ANVISA. CONSIDERANDO A APROVACAO DOS TERMOS DO PARECER NO 337/PGF/EA/2010, BEM COMO A PORTARIA INTERMINISTERIAL NO 1065 DE 24/05/2012, ENCAMINHA-SE O PRESENTE PEDIDO PARA AS PROVIDENCIAS CABIVEIS. |
|
| B25G | Requested change of headquarter approved |
Owner name: TARGEGEN, INC. (US) |
|
| B25A | Requested transfer of rights approved |
Owner name: IMPACT BIOMEDICINES, INC. (US) |
|
| B07E | Notification of approval relating to section 229 industrial property law [chapter 7.5 patent gazette] | ||
| B06A | Patent application procedure suspended [chapter 6.1 patent gazette] | ||
| B06A | Patent application procedure suspended [chapter 6.1 patent gazette] | ||
| B11B | Dismissal acc. art. 36, par 1 of ipl - no reply within 90 days to fullfil the necessary requirements |