JP2008545652A - ｃ−ｋｉｔおよびｃ−ｆｍｓ活性を調節する化合物およびその用途 - Google Patents
ｃ−ｋｉｔおよびｃ−ｆｍｓ活性を調節する化合物およびその用途 Download PDFInfo
- Publication number
- JP2008545652A JP2008545652A JP2008512402A JP2008512402A JP2008545652A JP 2008545652 A JP2008545652 A JP 2008545652A JP 2008512402 A JP2008512402 A JP 2008512402A JP 2008512402 A JP2008512402 A JP 2008512402A JP 2008545652 A JP2008545652 A JP 2008545652A
- Authority
- JP
- Japan
- Prior art keywords
- fluoro
- nhr
- group
- substituted
- optionally substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 283
- 108010014608 Proto-Oncogene Proteins c-kit Proteins 0.000 title claims abstract description 169
- 102000016971 Proto-Oncogene Proteins c-kit Human genes 0.000 title claims abstract description 166
- 108010058398 Macrophage Colony-Stimulating Factor Receptor Proteins 0.000 title claims abstract description 115
- 230000000694 effects Effects 0.000 title description 70
- 238000000034 method Methods 0.000 claims abstract description 83
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 81
- 201000010099 disease Diseases 0.000 claims abstract description 78
- 239000000203 mixture Substances 0.000 claims abstract description 44
- 230000001404 mediated effect Effects 0.000 claims abstract description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 247
- 125000003545 alkoxy group Chemical group 0.000 claims description 156
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 126
- 125000001424 substituent group Chemical group 0.000 claims description 113
- 125000001153 fluoro group Chemical group F* 0.000 claims description 111
- 239000001257 hydrogen Substances 0.000 claims description 111
- 229910052739 hydrogen Inorganic materials 0.000 claims description 111
- 125000004414 alkyl thio group Chemical group 0.000 claims description 110
- 125000001072 heteroaryl group Chemical group 0.000 claims description 97
- 229910052799 carbon Inorganic materials 0.000 claims description 93
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 87
- 229910052757 nitrogen Inorganic materials 0.000 claims description 79
- 229910052736 halogen Inorganic materials 0.000 claims description 78
- 150000002367 halogens Chemical class 0.000 claims description 78
- -1 monoalkylamino Chemical group 0.000 claims description 70
- 125000003118 aryl group Chemical group 0.000 claims description 65
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 52
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 52
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 46
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 41
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 40
- 125000003342 alkenyl group Chemical group 0.000 claims description 38
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 36
- 238000006467 substitution reaction Methods 0.000 claims description 35
- 125000000304 alkynyl group Chemical group 0.000 claims description 33
- 206010028980 Neoplasm Diseases 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 31
- 101100240528 Caenorhabditis elegans nhr-23 gene Proteins 0.000 claims description 30
- 239000000651 prodrug Substances 0.000 claims description 30
- 229940002612 prodrug Drugs 0.000 claims description 30
- 125000003107 substituted aryl group Chemical group 0.000 claims description 29
- 229910052760 oxygen Inorganic materials 0.000 claims description 28
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 28
- 125000002947 alkylene group Chemical group 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 208000008585 mastocytosis Diseases 0.000 claims description 21
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 19
- 229910052720 vanadium Inorganic materials 0.000 claims description 19
- 230000001965 increasing effect Effects 0.000 claims description 18
- 229910052717 sulfur Inorganic materials 0.000 claims description 18
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims description 17
- 201000006512 mast cell neoplasm Diseases 0.000 claims description 17
- 101100294106 Caenorhabditis elegans nhr-3 gene Proteins 0.000 claims description 16
- 201000011243 gastrointestinal stromal tumor Diseases 0.000 claims description 16
- 208000006971 mastocytoma Diseases 0.000 claims description 16
- 229910052770 Uranium Inorganic materials 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 15
- 229910052721 tungsten Inorganic materials 0.000 claims description 15
- 150000001345 alkine derivatives Chemical class 0.000 claims description 14
- 206010041067 Small cell lung cancer Diseases 0.000 claims description 13
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 13
- 208000000587 small cell lung carcinoma Diseases 0.000 claims description 13
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 13
- 206010022489 Insulin Resistance Diseases 0.000 claims description 12
- 150000001336 alkenes Chemical class 0.000 claims description 12
- 125000003282 alkyl amino group Chemical group 0.000 claims description 12
- 208000006673 asthma Diseases 0.000 claims description 12
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 12
- 206010051066 Gastrointestinal stromal tumour Diseases 0.000 claims description 11
- 206010018364 Glomerulonephritis Diseases 0.000 claims description 11
- 208000024313 Testicular Neoplasms Diseases 0.000 claims description 11
- 206010052779 Transplant rejections Diseases 0.000 claims description 11
- 201000006417 multiple sclerosis Diseases 0.000 claims description 11
- 201000003120 testicular cancer Diseases 0.000 claims description 11
- 125000004001 thioalkyl group Chemical group 0.000 claims description 11
- 201000001320 Atherosclerosis Diseases 0.000 claims description 10
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 10
- 206010009944 Colon cancer Diseases 0.000 claims description 10
- 206010057644 Testis cancer Diseases 0.000 claims description 10
- 208000005017 glioblastoma Diseases 0.000 claims description 10
- 208000032839 leukemia Diseases 0.000 claims description 10
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 10
- 206010014561 Emphysema Diseases 0.000 claims description 9
- 206010017076 Fracture Diseases 0.000 claims description 9
- 208000009905 Neurofibromatoses Diseases 0.000 claims description 9
- 206010039491 Sarcoma Diseases 0.000 claims description 9
- 230000001684 chronic effect Effects 0.000 claims description 9
- 230000002757 inflammatory effect Effects 0.000 claims description 9
- 201000004931 neurofibromatosis Diseases 0.000 claims description 9
- 208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims description 8
- 208000014697 Acute lymphocytic leukaemia Diseases 0.000 claims description 8
- 206010003571 Astrocytoma Diseases 0.000 claims description 8
- 208000010392 Bone Fractures Diseases 0.000 claims description 8
- 206010006187 Breast cancer Diseases 0.000 claims description 8
- 208000026310 Breast neoplasm Diseases 0.000 claims description 8
- 241000282465 Canis Species 0.000 claims description 8
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 8
- 208000037147 Hypercalcaemia Diseases 0.000 claims description 8
- 206010020880 Hypertrophy Diseases 0.000 claims description 8
- 208000001132 Osteoporosis Diseases 0.000 claims description 8
- 206010033128 Ovarian cancer Diseases 0.000 claims description 8
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 8
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims description 8
- 210000000988 bone and bone Anatomy 0.000 claims description 8
- 210000005002 female reproductive tract Anatomy 0.000 claims description 8
- 230000000148 hypercalcaemia Effects 0.000 claims description 8
- 208000030915 hypercalcemia disease Diseases 0.000 claims description 8
- 201000001421 hyperglycemia Diseases 0.000 claims description 8
- 201000004933 in situ carcinoma Diseases 0.000 claims description 8
- 230000004130 lipolysis Effects 0.000 claims description 8
- 201000001441 melanoma Diseases 0.000 claims description 8
- 125000002950 monocyclic group Chemical group 0.000 claims description 8
- 230000009826 neoplastic cell growth Effects 0.000 claims description 8
- 210000004116 schwann cell Anatomy 0.000 claims description 8
- 208000011580 syndromic disease Diseases 0.000 claims description 8
- 201000009030 Carcinoma Diseases 0.000 claims description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 7
- 208000034578 Multiple myelomas Diseases 0.000 claims description 7
- 206010035226 Plasma cell myeloma Diseases 0.000 claims description 7
- 206010038540 Renal tubular necrosis Diseases 0.000 claims description 7
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 7
- 201000010105 allergic rhinitis Diseases 0.000 claims description 7
- 201000010989 colorectal carcinoma Diseases 0.000 claims description 7
- 201000006334 interstitial nephritis Diseases 0.000 claims description 7
- 201000008968 osteosarcoma Diseases 0.000 claims description 7
- 208000005777 Lupus Nephritis Diseases 0.000 claims description 6
- 206010029260 Neuroblastoma Diseases 0.000 claims description 6
- 125000005549 heteroarylene group Chemical group 0.000 claims description 6
- 201000008383 nephritis Diseases 0.000 claims description 6
- 125000006578 monocyclic heterocycloalkyl group Chemical group 0.000 claims description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims description 5
- 229910052700 potassium Inorganic materials 0.000 claims description 5
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 4
- 206010014950 Eosinophilia Diseases 0.000 claims description 4
- 206010027476 Metastases Diseases 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 230000009401 metastasis Effects 0.000 claims description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 4
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims description 3
- 210000001185 bone marrow Anatomy 0.000 claims description 3
- 208000033679 diabetic kidney disease Diseases 0.000 claims description 3
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 2
- 238000010276 construction Methods 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 19
- 210000004027 cell Anatomy 0.000 description 88
- 238000009739 binding Methods 0.000 description 49
- 230000027455 binding Effects 0.000 description 47
- 150000007523 nucleic acids Chemical group 0.000 description 43
- 108090000765 processed proteins & peptides Proteins 0.000 description 41
- 108091000080 Phosphotransferase Proteins 0.000 description 40
- 102000020233 phosphotransferase Human genes 0.000 description 40
- 108090000623 proteins and genes Proteins 0.000 description 40
- 108010046938 Macrophage Colony-Stimulating Factor Proteins 0.000 description 39
- 102000007651 Macrophage Colony-Stimulating Factor Human genes 0.000 description 38
- 210000003630 histaminocyte Anatomy 0.000 description 37
- 102000004196 processed proteins & peptides Human genes 0.000 description 37
- 108020004707 nucleic acids Proteins 0.000 description 35
- 102000039446 nucleic acids Human genes 0.000 description 35
- 230000014509 gene expression Effects 0.000 description 34
- 238000003556 assay Methods 0.000 description 31
- 229920001184 polypeptide Polymers 0.000 description 28
- 125000004429 atom Chemical group 0.000 description 27
- 210000002540 macrophage Anatomy 0.000 description 27
- 239000003814 drug Substances 0.000 description 25
- 239000013598 vector Substances 0.000 description 25
- 102000004169 proteins and genes Human genes 0.000 description 24
- 229940079593 drug Drugs 0.000 description 22
- 230000005764 inhibitory process Effects 0.000 description 22
- 239000003446 ligand Substances 0.000 description 22
- 230000035772 mutation Effects 0.000 description 22
- 235000018102 proteins Nutrition 0.000 description 21
- 241001465754 Metazoa Species 0.000 description 19
- 210000003979 eosinophil Anatomy 0.000 description 19
- 108020004414 DNA Proteins 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- 206010020751 Hypersensitivity Diseases 0.000 description 16
- 230000007815 allergy Effects 0.000 description 16
- 238000009472 formulation Methods 0.000 description 16
- 210000004369 blood Anatomy 0.000 description 15
- 239000008280 blood Substances 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- 102000004190 Enzymes Human genes 0.000 description 14
- 108090000790 Enzymes Proteins 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 229940088598 enzyme Drugs 0.000 description 14
- 239000013604 expression vector Substances 0.000 description 14
- 230000003993 interaction Effects 0.000 description 14
- 238000004519 manufacturing process Methods 0.000 description 14
- 102000005962 receptors Human genes 0.000 description 14
- 108020003175 receptors Proteins 0.000 description 14
- 201000011510 cancer Diseases 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 230000001225 therapeutic effect Effects 0.000 description 13
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 description 12
- 241000699670 Mus sp. Species 0.000 description 12
- 239000002253 acid Chemical group 0.000 description 12
- 230000004913 activation Effects 0.000 description 12
- 208000026935 allergic disease Diseases 0.000 description 12
- 239000002207 metabolite Substances 0.000 description 12
- 238000000746 purification Methods 0.000 description 12
- 230000004071 biological effect Effects 0.000 description 11
- 238000002875 fluorescence polarization Methods 0.000 description 11
- 230000004054 inflammatory process Effects 0.000 description 11
- 238000002560 therapeutic procedure Methods 0.000 description 11
- 210000001519 tissue Anatomy 0.000 description 11
- 235000001014 amino acid Nutrition 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 10
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 10
- 238000011161 development Methods 0.000 description 10
- 230000018109 developmental process Effects 0.000 description 10
- 238000007254 oxidation reaction Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 208000024891 symptom Diseases 0.000 description 10
- 206010061218 Inflammation Diseases 0.000 description 9
- 150000001413 amino acids Chemical class 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 238000010367 cloning Methods 0.000 description 9
- 230000004069 differentiation Effects 0.000 description 9
- 102000037865 fusion proteins Human genes 0.000 description 9
- 108020001507 fusion proteins Proteins 0.000 description 9
- 238000013537 high throughput screening Methods 0.000 description 9
- 208000027866 inflammatory disease Diseases 0.000 description 9
- 239000003112 inhibitor Substances 0.000 description 9
- 125000005647 linker group Chemical group 0.000 description 9
- 238000006722 reduction reaction Methods 0.000 description 9
- 230000001105 regulatory effect Effects 0.000 description 9
- 239000000523 sample Substances 0.000 description 9
- 230000004083 survival effect Effects 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 8
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 8
- 230000003213 activating effect Effects 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 8
- 230000008901 benefit Effects 0.000 description 8
- 239000000969 carrier Substances 0.000 description 8
- 230000004663 cell proliferation Effects 0.000 description 8
- 230000007423 decrease Effects 0.000 description 8
- 230000007170 pathology Effects 0.000 description 8
- 239000013612 plasmid Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 description 7
- 108091026890 Coding region Proteins 0.000 description 7
- 108091028043 Nucleic acid sequence Proteins 0.000 description 7
- 101150038994 PDGFRA gene Proteins 0.000 description 7
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 7
- 102000010780 Platelet-Derived Growth Factor Human genes 0.000 description 7
- 108010038512 Platelet-Derived Growth Factor Proteins 0.000 description 7
- 230000035508 accumulation Effects 0.000 description 7
- 238000009825 accumulation Methods 0.000 description 7
- 230000003305 autocrine Effects 0.000 description 7
- 230000033228 biological regulation Effects 0.000 description 7
- 230000000875 corresponding effect Effects 0.000 description 7
- 230000006870 function Effects 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- KTUFNOKKBVMGRW-UHFFFAOYSA-N imatinib Chemical compound C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 KTUFNOKKBVMGRW-UHFFFAOYSA-N 0.000 description 7
- 238000001727 in vivo Methods 0.000 description 7
- 239000002609 medium Substances 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 210000001616 monocyte Anatomy 0.000 description 7
- 210000002997 osteoclast Anatomy 0.000 description 7
- 230000003647 oxidation Effects 0.000 description 7
- 230000035755 proliferation Effects 0.000 description 7
- 238000002198 surface plasmon resonance spectroscopy Methods 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 102000004127 Cytokines Human genes 0.000 description 6
- 108090000695 Cytokines Proteins 0.000 description 6
- 229920002307 Dextran Polymers 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 108060003951 Immunoglobulin Proteins 0.000 description 6
- 239000005517 L01XE01 - Imatinib Substances 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
- 241000700605 Viruses Species 0.000 description 6
- 125000003275 alpha amino acid group Chemical group 0.000 description 6
- 125000000539 amino acid group Chemical group 0.000 description 6
- 230000006907 apoptotic process Effects 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 238000002866 fluorescence resonance energy transfer Methods 0.000 description 6
- 230000012010 growth Effects 0.000 description 6
- 239000003102 growth factor Substances 0.000 description 6
- 102000018358 immunoglobulin Human genes 0.000 description 6
- 238000000338 in vitro Methods 0.000 description 6
- 238000011835 investigation Methods 0.000 description 6
- 210000004072 lung Anatomy 0.000 description 6
- 230000003211 malignant effect Effects 0.000 description 6
- 210000004962 mammalian cell Anatomy 0.000 description 6
- 239000011159 matrix material Substances 0.000 description 6
- 108020004999 messenger RNA Proteins 0.000 description 6
- 229920001223 polyethylene glycol Polymers 0.000 description 6
- 230000009467 reduction Effects 0.000 description 6
- 230000002829 reductive effect Effects 0.000 description 6
- 238000012216 screening Methods 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
- MVXVYAKCVDQRLW-UHFFFAOYSA-N 1h-pyrrolo[2,3-b]pyridine Chemical compound C1=CN=C2NC=CC2=C1 MVXVYAKCVDQRLW-UHFFFAOYSA-N 0.000 description 5
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 108010002386 Interleukin-3 Proteins 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 108700020796 Oncogene Proteins 0.000 description 5
- 239000002202 Polyethylene glycol Substances 0.000 description 5
- 102000001253 Protein Kinase Human genes 0.000 description 5
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 5
- 230000002159 abnormal effect Effects 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 235000011054 acetic acid Nutrition 0.000 description 5
- 230000001154 acute effect Effects 0.000 description 5
- 230000003321 amplification Effects 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 230000003197 catalytic effect Effects 0.000 description 5
- 230000001413 cellular effect Effects 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000002299 complementary DNA Substances 0.000 description 5
- 230000006378 damage Effects 0.000 description 5
- 230000003247 decreasing effect Effects 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 239000012634 fragment Substances 0.000 description 5
- 229960002411 imatinib Drugs 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 230000007246 mechanism Effects 0.000 description 5
- 239000012528 membrane Substances 0.000 description 5
- 230000004060 metabolic process Effects 0.000 description 5
- 238000003199 nucleic acid amplification method Methods 0.000 description 5
- 210000000056 organ Anatomy 0.000 description 5
- 239000000546 pharmaceutical excipient Substances 0.000 description 5
- 230000000144 pharmacologic effect Effects 0.000 description 5
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 108060006633 protein kinase Proteins 0.000 description 5
- 230000010076 replication Effects 0.000 description 5
- 238000012552 review Methods 0.000 description 5
- 210000003491 skin Anatomy 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 210000000130 stem cell Anatomy 0.000 description 5
- 238000013518 transcription Methods 0.000 description 5
- 230000035897 transcription Effects 0.000 description 5
- 238000001890 transfection Methods 0.000 description 5
- 238000013519 translation Methods 0.000 description 5
- 230000032258 transport Effects 0.000 description 5
- 230000003612 virological effect Effects 0.000 description 5
- MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 description 4
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 241000283690 Bos taurus Species 0.000 description 4
- 241000282472 Canis lupus familiaris Species 0.000 description 4
- 241000283086 Equidae Species 0.000 description 4
- 241000282326 Felis catus Species 0.000 description 4
- 108010010803 Gelatin Proteins 0.000 description 4
- 102000004269 Granulocyte Colony-Stimulating Factor Human genes 0.000 description 4
- 108010017080 Granulocyte Colony-Stimulating Factor Proteins 0.000 description 4
- 108010017213 Granulocyte-Macrophage Colony-Stimulating Factor Proteins 0.000 description 4
- 102100039620 Granulocyte-macrophage colony-stimulating factor Human genes 0.000 description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
- 241000124008 Mammalia Species 0.000 description 4
- 206010027452 Metastases to bone Diseases 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 241000288906 Primates Species 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 4
- 201000010208 Seminoma Diseases 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- 108010039445 Stem Cell Factor Proteins 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 210000001132 alveolar macrophage Anatomy 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 238000004113 cell culture Methods 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 238000003776 cleavage reaction Methods 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 206010012601 diabetes mellitus Diseases 0.000 description 4
- 238000010494 dissociation reaction Methods 0.000 description 4
- 230000005593 dissociations Effects 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 239000008273 gelatin Substances 0.000 description 4
- 229920000159 gelatin Polymers 0.000 description 4
- 229940014259 gelatin Drugs 0.000 description 4
- 235000019322 gelatine Nutrition 0.000 description 4
- 235000011852 gelatine desserts Nutrition 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000009396 hybridization Methods 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 230000001976 improved effect Effects 0.000 description 4
- 230000001939 inductive effect Effects 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 210000002510 keratinocyte Anatomy 0.000 description 4
- 239000008101 lactose Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 208000030159 metabolic disease Diseases 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000002773 nucleotide Substances 0.000 description 4
- 125000003729 nucleotide group Chemical group 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 230000002062 proliferating effect Effects 0.000 description 4
- LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 238000002821 scintillation proximity assay Methods 0.000 description 4
- 230000007017 scission Effects 0.000 description 4
- 230000011664 signaling Effects 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 230000000699 topical effect Effects 0.000 description 4
- 230000009466 transformation Effects 0.000 description 4
- IEUUDEWWMRQUDS-UHFFFAOYSA-N (6-azaniumylidene-1,6-dimethoxyhexylidene)azanium;dichloride Chemical compound Cl.Cl.COC(=N)CCCCC(=N)OC IEUUDEWWMRQUDS-UHFFFAOYSA-N 0.000 description 3
- 108091032973 (ribonucleotides)n+m Proteins 0.000 description 3
- 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 3
- 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 3
- NFLLKCVHYJRNRH-UHFFFAOYSA-N 8-chloro-1,3-dimethyl-7H-purine-2,6-dione 2-(diphenylmethyl)oxy-N,N-dimethylethanamine Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC(Cl)=N2.C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 NFLLKCVHYJRNRH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 101100007328 Cocos nucifera COS-1 gene Proteins 0.000 description 3
- 102000053602 DNA Human genes 0.000 description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 3
- 102000016942 Elastin Human genes 0.000 description 3
- 108010014258 Elastin Proteins 0.000 description 3
- 108010013369 Enteropeptidase Proteins 0.000 description 3
- 102100029727 Enteropeptidase Human genes 0.000 description 3
- CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical compound O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 0.000 description 3
- 229930182566 Gentamicin Natural products 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 241000238631 Hexapoda Species 0.000 description 3
- 241000282412 Homo Species 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 102100039064 Interleukin-3 Human genes 0.000 description 3
- 102000004889 Interleukin-6 Human genes 0.000 description 3
- 108090001005 Interleukin-6 Proteins 0.000 description 3
- 102000004890 Interleukin-8 Human genes 0.000 description 3
- 108090001007 Interleukin-8 Proteins 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- BKAYIFDRRZZKNF-VIFPVBQESA-N N-acetylcarnosine Chemical compound CC(=O)NCCC(=O)N[C@H](C(O)=O)CC1=CN=CN1 BKAYIFDRRZZKNF-VIFPVBQESA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 102000007056 Recombinant Fusion Proteins Human genes 0.000 description 3
- 108010008281 Recombinant Fusion Proteins Proteins 0.000 description 3
- 241000723873 Tobacco mosaic virus Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000005557 antagonist Substances 0.000 description 3
- 210000004436 artificial bacterial chromosome Anatomy 0.000 description 3
- 210000001106 artificial yeast chromosome Anatomy 0.000 description 3
- 230000001580 bacterial effect Effects 0.000 description 3
- 125000002619 bicyclic group Chemical group 0.000 description 3
- 230000033558 biomineral tissue development Effects 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 230000010261 cell growth Effects 0.000 description 3
- ZAIPMKNFIOOWCQ-UEKVPHQBSA-N cephalexin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CC=CC=C1 ZAIPMKNFIOOWCQ-UEKVPHQBSA-N 0.000 description 3
- 238000012512 characterization method Methods 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 3
- 229960001231 choline Drugs 0.000 description 3
- 210000000349 chromosome Anatomy 0.000 description 3
- 208000037976 chronic inflammation Diseases 0.000 description 3
- 201000009151 chronic rhinitis Diseases 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 230000002950 deficient Effects 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 238000002651 drug therapy Methods 0.000 description 3
- 230000009977 dual effect Effects 0.000 description 3
- 229920002549 elastin Polymers 0.000 description 3
- 238000006911 enzymatic reaction Methods 0.000 description 3
- 210000002950 fibroblast Anatomy 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 210000001035 gastrointestinal tract Anatomy 0.000 description 3
- 229960002518 gentamicin Drugs 0.000 description 3
- 210000004602 germ cell Anatomy 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 230000011132 hemopoiesis Effects 0.000 description 3
- 230000003301 hydrolyzing effect Effects 0.000 description 3
- 125000002883 imidazolyl group Chemical group 0.000 description 3
- 208000026278 immune system disease Diseases 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- 229940100601 interleukin-6 Drugs 0.000 description 3
- XKTZWUACRZHVAN-VADRZIEHSA-N interleukin-8 Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@@H](NC(C)=O)CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CCSC)C(=O)N1[C@H](CCC1)C(=O)N1[C@H](CCC1)C(=O)N[C@@H](C)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC=1C=CC(O)=CC=1)C(=O)N[C@H](CO)C(=O)N1[C@H](CCC1)C(N)=O)C1=CC=CC=C1 XKTZWUACRZHVAN-VADRZIEHSA-N 0.000 description 3
- 229940096397 interleukin-8 Drugs 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 210000003734 kidney Anatomy 0.000 description 3
- 208000017169 kidney disease Diseases 0.000 description 3
- 238000003674 kinase activity assay Methods 0.000 description 3
- 230000003902 lesion Effects 0.000 description 3
- 150000002632 lipids Chemical class 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 238000010369 molecular cloning Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 239000002798 polar solvent Substances 0.000 description 3
- 230000010287 polarization Effects 0.000 description 3
- 238000003752 polymerase chain reaction Methods 0.000 description 3
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 230000035935 pregnancy Effects 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- 125000003373 pyrazinyl group Chemical group 0.000 description 3
- 125000002098 pyridazinyl group Chemical group 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 125000000168 pyrrolyl group Chemical group 0.000 description 3
- 206010039083 rhinitis Diseases 0.000 description 3
- 125000006413 ring segment Chemical group 0.000 description 3
- 230000028327 secretion Effects 0.000 description 3
- 238000012163 sequencing technique Methods 0.000 description 3
- 230000019491 signal transduction Effects 0.000 description 3
- 150000003384 small molecules Chemical class 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 210000002536 stromal cell Anatomy 0.000 description 3
- 235000000346 sugar Nutrition 0.000 description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
- 125000000335 thiazolyl group Chemical group 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- 150000003573 thiols Chemical class 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- 230000010474 transient expression Effects 0.000 description 3
- 241000701161 unidentified adenovirus Species 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- BQWBEDSJTMWJAE-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[(2-iodoacetyl)amino]benzoate Chemical compound C1=CC(NC(=O)CI)=CC=C1C(=O)ON1C(=O)CCC1=O BQWBEDSJTMWJAE-UHFFFAOYSA-N 0.000 description 2
- AAWZDTNXLSGCEK-LNVDRNJUSA-N (3r,5r)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid Chemical class O[C@@H]1CC(O)(C(O)=O)C[C@@H](O)C1O AAWZDTNXLSGCEK-LNVDRNJUSA-N 0.000 description 2
- AASYSXRGODIQGY-UHFFFAOYSA-N 1-[1-(2,5-dioxopyrrol-1-yl)hexyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(CCCCC)N1C(=O)C=CC1=O AASYSXRGODIQGY-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- OKTWQKXBJUBAKS-WQADZSDSSA-N 2-[[(e,2r,3s)-2-amino-3-hydroxyoctadec-4-enoxy]-hydroxyphosphoryl]oxyethyl-trimethylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCC\C=C\[C@H](O)[C@H](N)COP(O)(=O)OCC[N+](C)(C)C OKTWQKXBJUBAKS-WQADZSDSSA-N 0.000 description 2
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- 208000028906 Abnormal bone structure Diseases 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 208000037260 Atherosclerotic Plaque Diseases 0.000 description 2
- 208000032800 BCR-ABL1 positive blast phase chronic myelogenous leukemia Diseases 0.000 description 2
- 208000004860 Blast Crisis Diseases 0.000 description 2
- YDNKGFDKKRUKPY-JHOUSYSJSA-N C16 ceramide Natural products CCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)C=CCCCCCCCCCCCCC YDNKGFDKKRUKPY-JHOUSYSJSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 241000282693 Cercopithecidae Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 108020004705 Codon Proteins 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
- 238000000018 DNA microarray Methods 0.000 description 2
- 241000702421 Dependoparvovirus Species 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 206010061818 Disease progression Diseases 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- 206010017993 Gastrointestinal neoplasms Diseases 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- 108010043121 Green Fluorescent Proteins Proteins 0.000 description 2
- 102000004144 Green Fluorescent Proteins Human genes 0.000 description 2
- 208000002250 Hematologic Neoplasms Diseases 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- 241000725303 Human immunodeficiency virus Species 0.000 description 2
- 241000341655 Human papillomavirus type 16 Species 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 102000000646 Interleukin-3 Human genes 0.000 description 2
- 108010002616 Interleukin-5 Proteins 0.000 description 2
- 102000000743 Interleukin-5 Human genes 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- 241000714177 Murine leukemia virus Species 0.000 description 2
- 241000699660 Mus musculus Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
- CRJGESKKUOMBCT-VQTJNVASSA-N N-acetylsphinganine Chemical compound CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)NC(C)=O CRJGESKKUOMBCT-VQTJNVASSA-N 0.000 description 2
- 150000001204 N-oxides Chemical class 0.000 description 2
- 208000034176 Neoplasms, Germ Cell and Embryonal Diseases 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 208000008589 Obesity Diseases 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 101710124951 Phospholipase C Proteins 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- 108020004511 Recombinant DNA Proteins 0.000 description 2
- 241000283984 Rodentia Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 241000713311 Simian immunodeficiency virus Species 0.000 description 2
- 108020004682 Single-Stranded DNA Proteins 0.000 description 2
- 101710166827 Sphingomyelinase Proteins 0.000 description 2
- 101710122751 Sphingomyelinase C Proteins 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 201000008736 Systemic mastocytosis Diseases 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- FUGOUWIFQWVBOZ-UHFFFAOYSA-N [3-(chloromethyl)pyrrolo[2,3-b]pyridin-1-yl]-tri(propan-2-yl)silane Chemical compound C1=CN=C2N([Si](C(C)C)(C(C)C)C(C)C)C=C(CCl)C2=C1 FUGOUWIFQWVBOZ-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 238000001042 affinity chromatography Methods 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 230000000172 allergic effect Effects 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 210000004102 animal cell Anatomy 0.000 description 2
- 238000003491 array Methods 0.000 description 2
- 206010003246 arthritis Diseases 0.000 description 2
- 210000004507 artificial chromosome Anatomy 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- 230000003143 atherosclerotic effect Effects 0.000 description 2
- 208000010668 atopic eczema Diseases 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 102000023732 binding proteins Human genes 0.000 description 2
- 108091008324 binding proteins Proteins 0.000 description 2
- 230000008827 biological function Effects 0.000 description 2
- ZGDJMMPBPMJJBR-UHFFFAOYSA-N bis(1H-indol-2-yl)diazene Chemical group c1c(N=Nc2cc3ccccc3[nH]2)[nH]c2ccccc12 ZGDJMMPBPMJJBR-UHFFFAOYSA-N 0.000 description 2
- 210000004204 blood vessel Anatomy 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 239000004067 bulking agent Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 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
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 231100000504 carcinogenesis Toxicity 0.000 description 2
- 230000024245 cell differentiation Effects 0.000 description 2
- 230000003915 cell function Effects 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 229940106189 ceramide Drugs 0.000 description 2
- ZVEQCJWYRWKARO-UHFFFAOYSA-N ceramide Natural products CCCCCCCCCCCCCCC(O)C(=O)NC(CO)C(O)C=CCCC=C(C)CCCCCCCCC ZVEQCJWYRWKARO-UHFFFAOYSA-N 0.000 description 2
- 239000002975 chemoattractant Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000002759 chromosomal effect Effects 0.000 description 2
- 208000023819 chronic asthma Diseases 0.000 description 2
- 235000015165 citric acid Nutrition 0.000 description 2
- 238000011260 co-administration Methods 0.000 description 2
- 230000000295 complement effect Effects 0.000 description 2
- 239000003246 corticosteroid Substances 0.000 description 2
- 229960001334 corticosteroids Drugs 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 229960000265 cromoglicic acid Drugs 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 2
- 230000002559 cytogenic effect Effects 0.000 description 2
- 230000001086 cytosolic effect Effects 0.000 description 2
- 238000006900 dealkylation reaction Methods 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- LRHXBHUTQWIZTN-UHFFFAOYSA-N dimethyl heptanediimidate;dihydrochloride Chemical compound Cl.Cl.COC(=N)CCCCCC(=N)OC LRHXBHUTQWIZTN-UHFFFAOYSA-N 0.000 description 2
- 230000005750 disease progression Effects 0.000 description 2
- VLARUOGDXDTHEH-UHFFFAOYSA-L disodium cromoglycate Chemical compound [Na+].[Na+].O1C(C([O-])=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C([O-])=O)O2 VLARUOGDXDTHEH-UHFFFAOYSA-L 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 230000005014 ectopic expression Effects 0.000 description 2
- 210000002889 endothelial cell Anatomy 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 210000003527 eukaryotic cell Anatomy 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 238000001506 fluorescence spectroscopy Methods 0.000 description 2
- 210000000497 foam cell Anatomy 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 229940080856 gleevec Drugs 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 239000005090 green fluorescent protein Substances 0.000 description 2
- 210000003958 hematopoietic stem cell Anatomy 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 125000000487 histidyl group Chemical group [H]N([H])C(C(=O)O*)C([H])([H])C1=C([H])N([H])C([H])=N1 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- RCBVKBFIWMOMHF-UHFFFAOYSA-L hydroxy-(hydroxy(dioxo)chromio)oxy-dioxochromium;pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1.O[Cr](=O)(=O)O[Cr](O)(=O)=O RCBVKBFIWMOMHF-UHFFFAOYSA-L 0.000 description 2
- 230000033444 hydroxylation Effects 0.000 description 2
- 238000005805 hydroxylation reaction Methods 0.000 description 2
- 230000001900 immune effect Effects 0.000 description 2
- 238000003018 immunoassay Methods 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- 230000008595 infiltration Effects 0.000 description 2
- 238000001764 infiltration Methods 0.000 description 2
- 230000004968 inflammatory condition Effects 0.000 description 2
- 229940076264 interleukin-3 Drugs 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000007918 intramuscular administration Methods 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 229940043355 kinase inhibitor Drugs 0.000 description 2
- 238000002372 labelling Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 210000002332 leydig cell Anatomy 0.000 description 2
- 229910052744 lithium Inorganic materials 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
- 238000012423 maintenance Methods 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 210000000723 mammalian artificial chromosome Anatomy 0.000 description 2
- 239000003550 marker Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 210000002752 melanocyte Anatomy 0.000 description 2
- 230000002503 metabolic effect Effects 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 239000003068 molecular probe Substances 0.000 description 2
- 238000010172 mouse model Methods 0.000 description 2
- 230000010309 neoplastic transformation Effects 0.000 description 2
- VVGIYYKRAMHVLU-UHFFFAOYSA-N newbouldiamide Natural products CCCCCCCCCCCCCCCCCCCC(O)C(O)C(O)C(CO)NC(=O)CCCCCCCCCCCCCCCCC VVGIYYKRAMHVLU-UHFFFAOYSA-N 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000012454 non-polar solvent Substances 0.000 description 2
- 230000009871 nonspecific binding Effects 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 235000020824 obesity Nutrition 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 230000008506 pathogenesis Effects 0.000 description 2
- 230000037361 pathway Effects 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 210000004214 philadelphia chromosome Anatomy 0.000 description 2
- PHEDXBVPIONUQT-RGYGYFBISA-N phorbol 13-acetate 12-myristate Chemical compound C([C@]1(O)C(=O)C(C)=C[C@H]1[C@@]1(O)[C@H](C)[C@H]2OC(=O)CCCCCCCCCCCCC)C(CO)=C[C@H]1[C@H]1[C@]2(OC(C)=O)C1(C)C PHEDXBVPIONUQT-RGYGYFBISA-N 0.000 description 2
- 229950004354 phosphorylcholine Drugs 0.000 description 2
- PYJNAPOPMIJKJZ-UHFFFAOYSA-N phosphorylcholine chloride Chemical compound [Cl-].C[N+](C)(C)CCOP(O)(O)=O PYJNAPOPMIJKJZ-UHFFFAOYSA-N 0.000 description 2
- 239000003757 phosphotransferase inhibitor Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 230000035479 physiological effects, processes and functions Effects 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920002704 polyhistidine Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 description 2
- 210000001236 prokaryotic cell Anatomy 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 238000000159 protein binding assay Methods 0.000 description 2
- 239000003586 protic polar solvent Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000003127 radioimmunoassay Methods 0.000 description 2
- 230000006798 recombination Effects 0.000 description 2
- 210000002345 respiratory system Anatomy 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 230000001177 retroviral effect Effects 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 102000014452 scavenger receptors Human genes 0.000 description 2
- 108010078070 scavenger receptors Proteins 0.000 description 2
- 238000007423 screening assay Methods 0.000 description 2
- 210000000717 sertoli cell Anatomy 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- HHSGWIABCIVPJT-UHFFFAOYSA-M sodium;1-[4-[(2-iodoacetyl)amino]benzoyl]oxy-2,5-dioxopyrrolidine-3-sulfonate Chemical compound [Na+].O=C1C(S(=O)(=O)[O-])CC(=O)N1OC(=O)C1=CC=C(NC(=O)CI)C=C1 HHSGWIABCIVPJT-UHFFFAOYSA-M 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 238000002798 spectrophotometry method Methods 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 150000008163 sugars Chemical class 0.000 description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 210000001550 testis Anatomy 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- 150000003606 tin compounds Chemical class 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 238000011830 transgenic mouse model Methods 0.000 description 2
- 125000001425 triazolyl group Chemical group 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
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 2
- 210000004881 tumor cell Anatomy 0.000 description 2
- 125000001493 tyrosinyl group Chemical group [H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 2
- 238000012036 ultra high throughput screening Methods 0.000 description 2
- 241000701447 unidentified baculovirus Species 0.000 description 2
- 208000019553 vascular disease Diseases 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- WWUZIQQURGPMPG-UHFFFAOYSA-N (-)-D-erythro-Sphingosine Natural products CCCCCCCCCCCCCC=CC(O)C(N)CO WWUZIQQURGPMPG-UHFFFAOYSA-N 0.000 description 1
- NKUZQMZWTZAPSN-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-bromoacetate Chemical compound BrCC(=O)ON1C(=O)CCC1=O NKUZQMZWTZAPSN-UHFFFAOYSA-N 0.000 description 1
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- DIGQNXIGRZPYDK-WKSCXVIASA-N (2R)-6-amino-2-[[2-[[(2S)-2-[[2-[[(2R)-2-[[(2S)-2-[[(2R,3S)-2-[[2-[[(2S)-2-[[2-[[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2S,3S)-2-[[(2R)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[2-[[(2S)-2-[[(2R)-2-[[2-[[2-[[2-[(2-amino-1-hydroxyethylidene)amino]-3-carboxy-1-hydroxypropylidene]amino]-1-hydroxy-3-sulfanylpropylidene]amino]-1-hydroxyethylidene]amino]-1-hydroxy-3-sulfanylpropylidene]amino]-1,3-dihydroxypropylidene]amino]-1-hydroxyethylidene]amino]-1-hydroxypropylidene]amino]-1,3-dihydroxypropylidene]amino]-1,3-dihydroxypropylidene]amino]-1-hydroxy-3-sulfanylpropylidene]amino]-1,3-dihydroxybutylidene]amino]-1-hydroxy-3-sulfanylpropylidene]amino]-1-hydroxypropylidene]amino]-1,3-dihydroxypropylidene]amino]-1-hydroxyethylidene]amino]-1,5-dihydroxy-5-iminopentylidene]amino]-1-hydroxy-3-sulfanylpropylidene]amino]-1,3-dihydroxybutylidene]amino]-1-hydroxy-3-sulfanylpropylidene]amino]-1,3-dihydroxypropylidene]amino]-1-hydroxyethylidene]amino]-1-hydroxy-3-sulfanylpropylidene]amino]-1-hydroxyethylidene]amino]hexanoic acid Chemical compound C[C@@H]([C@@H](C(=N[C@@H](CS)C(=N[C@@H](C)C(=N[C@@H](CO)C(=NCC(=N[C@@H](CCC(=N)O)C(=NC(CS)C(=N[C@H]([C@H](C)O)C(=N[C@H](CS)C(=N[C@H](CO)C(=NCC(=N[C@H](CS)C(=NCC(=N[C@H](CCCCN)C(=O)O)O)O)O)O)O)O)O)O)O)O)O)O)O)N=C([C@H](CS)N=C([C@H](CO)N=C([C@H](CO)N=C([C@H](C)N=C(CN=C([C@H](CO)N=C([C@H](CS)N=C(CN=C(C(CS)N=C(C(CC(=O)O)N=C(CN)O)O)O)O)O)O)O)O)O)O)O)O DIGQNXIGRZPYDK-WKSCXVIASA-N 0.000 description 1
- MLIWQXBKMZNZNF-KUHOPJCQSA-N (2e)-2,6-bis[(4-azidophenyl)methylidene]-4-methylcyclohexan-1-one Chemical compound O=C1\C(=C\C=2C=CC(=CC=2)N=[N+]=[N-])CC(C)CC1=CC1=CC=C(N=[N+]=[N-])C=C1 MLIWQXBKMZNZNF-KUHOPJCQSA-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
- JIQXIIYJBWAXPD-UHFFFAOYSA-N (6-anilinopyridin-3-yl)-(1h-pyrrolo[2,3-b]pyridin-3-yl)methanone Chemical compound C=1NC2=NC=CC=C2C=1C(=O)C(C=N1)=CC=C1NC1=CC=CC=C1 JIQXIIYJBWAXPD-UHFFFAOYSA-N 0.000 description 1
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 1
- WHTVZRBIWZFKQO-AWEZNQCLSA-N (S)-chloroquine Chemical compound ClC1=CC=C2C(N[C@@H](C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-AWEZNQCLSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- RRHVLMJIJCYTHX-UHFFFAOYSA-N 1-[3,5-dimethyl-4-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)pyrazol-1-yl]-3-phenylpropan-1-one Chemical compound CC1=C(CC=2C3=CC=CN=C3NC=2)C(C)=NN1C(=O)CCC1=CC=CC=C1 RRHVLMJIJCYTHX-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
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical group C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- RNHMOWMWHGHAKX-UHFFFAOYSA-N 1h-pyrrolo[2,3-b]pyridin-3-yl-[6-(thiophen-2-ylmethylamino)pyridin-3-yl]methanone Chemical compound C=1NC2=NC=CC=C2C=1C(=O)C(C=N1)=CC=C1NCC1=CC=CS1 RNHMOWMWHGHAKX-UHFFFAOYSA-N 0.000 description 1
- NLOLOGVDYVWASY-UHFFFAOYSA-N 1h-pyrrolo[2,3-b]pyridin-3-yl-[6-[[4-(trifluoromethyl)phenyl]methylamino]pyridin-3-yl]methanol Chemical compound C=1NC2=NC=CC=C2C=1C(O)C(C=N1)=CC=C1NCC1=CC=C(C(F)(F)F)C=C1 NLOLOGVDYVWASY-UHFFFAOYSA-N 0.000 description 1
- SDCNCMMJSOXIRT-UHFFFAOYSA-N 1h-pyrrolo[2,3-b]pyridin-3-yl-[6-[[4-(trifluoromethyl)phenyl]methylamino]pyridin-3-yl]methanone Chemical compound C1=CC(C(F)(F)F)=CC=C1CNC1=CC=C(C(=O)C=2C3=CC=CN=C3NC=2)C=N1 SDCNCMMJSOXIRT-UHFFFAOYSA-N 0.000 description 1
- XYPISWUKQGWYGX-UHFFFAOYSA-N 2,2,2-trifluoroethaneperoxoic acid Chemical compound OOC(=O)C(F)(F)F XYPISWUKQGWYGX-UHFFFAOYSA-N 0.000 description 1
- RVWUHFFPEOKYLB-UHFFFAOYSA-N 2,2,6,6-tetramethyl-1-oxidopiperidin-1-ium Chemical compound CC1(C)CCCC(C)(C)[NH+]1[O-] RVWUHFFPEOKYLB-UHFFFAOYSA-N 0.000 description 1
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 1
- GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 description 1
- HZLCGUXUOFWCCN-UHFFFAOYSA-N 2-hydroxynonadecane-1,2,3-tricarboxylic acid Chemical compound CCCCCCCCCCCCCCCCC(C(O)=O)C(O)(C(O)=O)CC(O)=O HZLCGUXUOFWCCN-UHFFFAOYSA-N 0.000 description 1
- JHWIEAWILPSRMU-UHFFFAOYSA-N 2-methyl-3-pyrimidin-4-ylpropanoic acid Chemical compound OC(=O)C(C)CC1=CC=NC=N1 JHWIEAWILPSRMU-UHFFFAOYSA-N 0.000 description 1
- DVGKRPYUFRZAQW-UHFFFAOYSA-N 3 prime Natural products CC(=O)NC1OC(CC(O)C1C(O)C(O)CO)(OC2C(O)C(CO)OC(OC3C(O)C(O)C(O)OC3CO)C2O)C(=O)O DVGKRPYUFRZAQW-UHFFFAOYSA-N 0.000 description 1
- RDEMTGSOQJARJF-UHFFFAOYSA-N 3,5-dimethyl-n-phenyl-4-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)pyrazole-1-carboxamide Chemical compound CC1=C(CC=2C3=CC=CN=C3NC=2)C(C)=NN1C(=O)NC1=CC=CC=C1 RDEMTGSOQJARJF-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
- VCGYLADNFNWOEJ-UHFFFAOYSA-N 3-[(1-butylsulfonyl-3,5-dimethylpyrazol-4-yl)methyl]-1h-pyrrolo[2,3-b]pyridine Chemical compound CCCCS(=O)(=O)N1N=C(C)C(CC=2C3=CC=CN=C3NC=2)=C1C VCGYLADNFNWOEJ-UHFFFAOYSA-N 0.000 description 1
- DELYZOYJZTWTIW-UHFFFAOYSA-N 3-[(5-chloro-3-methyl-1-phenylpyrazol-4-yl)-methoxymethyl]-1h-pyrrolo[2,3-b]pyridine Chemical compound C=1NC2=NC=CC=C2C=1C(OC)C(=C1Cl)C(C)=NN1C1=CC=CC=C1 DELYZOYJZTWTIW-UHFFFAOYSA-N 0.000 description 1
- QCSQMEQECMEOBB-UHFFFAOYSA-N 3-[(5-chloro-3-methyl-1-phenylpyrazol-4-yl)methyl]-1h-pyrrolo[2,3-b]pyridine Chemical compound ClC1=C(CC=2C3=CC=CN=C3NC=2)C(C)=NN1C1=CC=CC=C1 QCSQMEQECMEOBB-UHFFFAOYSA-N 0.000 description 1
- XUQRDPWSDFONOP-UHFFFAOYSA-N 3-[(6-methoxypyridin-3-yl)methyl]-4-thiophen-3-yl-1h-pyrrolo[2,3-b]pyridine Chemical compound C1=NC(OC)=CC=C1CC1=CNC2=NC=CC(C3=CSC=C3)=C12 XUQRDPWSDFONOP-UHFFFAOYSA-N 0.000 description 1
- BSJWRNUQVISVIE-UHFFFAOYSA-N 3-[(6-propan-2-ylpyridin-3-yl)methyl]-1h-pyrrolo[2,3-b]pyridine Chemical compound C1=NC(C(C)C)=CC=C1CC1=CNC2=NC=CC=C12 BSJWRNUQVISVIE-UHFFFAOYSA-N 0.000 description 1
- CKBYHIWAUQYWNH-UHFFFAOYSA-N 3-[[6-[(2-methylpropan-2-yl)oxy]pyridin-3-yl]methyl]-1h-pyrrolo[2,3-b]pyridine Chemical compound C1=NC(OC(C)(C)C)=CC=C1CC1=CNC2=NC=CC=C12 CKBYHIWAUQYWNH-UHFFFAOYSA-N 0.000 description 1
- NEWMLAUJRYFIFP-UHFFFAOYSA-N 3-[[6-[(4-chlorophenyl)methylamino]pyridin-3-yl]methyl]-1h-pyrrolo[2,3-b]pyridin-5-ol Chemical compound C12=CC(O)=CN=C2NC=C1CC(C=N1)=CC=C1NCC1=CC=C(Cl)C=C1 NEWMLAUJRYFIFP-UHFFFAOYSA-N 0.000 description 1
- APKGRRLSSTWJGF-UHFFFAOYSA-N 3-[[6-[[3-(trifluoromethyl)phenyl]methoxy]pyridin-3-yl]methyl]-1h-pyrrolo[2,3-b]pyridine Chemical compound FC(F)(F)C1=CC=CC(COC=2N=CC(CC=3C4=CC=CN=C4NC=3)=CC=2)=C1 APKGRRLSSTWJGF-UHFFFAOYSA-N 0.000 description 1
- YUMYNXVGFKTRQX-UHFFFAOYSA-N 3-[[6-[[4-(trifluoromethyl)phenyl]methylamino]pyridin-3-yl]methyl]-1h-pyrrolo[2,3-b]pyridin-5-ol Chemical compound C12=CC(O)=CN=C2NC=C1CC(C=N1)=CC=C1NCC1=CC=C(C(F)(F)F)C=C1 YUMYNXVGFKTRQX-UHFFFAOYSA-N 0.000 description 1
- JYLNVJYYQQXNEK-UHFFFAOYSA-N 3-amino-2-(4-chlorophenyl)-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(CN)C1=CC=C(Cl)C=C1 JYLNVJYYQQXNEK-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
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- FWMNVWWHGCHHJJ-SKKKGAJSSA-N 4-amino-1-[(2r)-6-amino-2-[[(2r)-2-[[(2r)-2-[[(2r)-2-amino-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoyl]amino]hexanoyl]piperidine-4-carboxylic acid Chemical compound C([C@H](C(=O)N[C@H](CC(C)C)C(=O)N[C@H](CCCCN)C(=O)N1CCC(N)(CC1)C(O)=O)NC(=O)[C@H](N)CC=1C=CC=CC=1)C1=CC=CC=C1 FWMNVWWHGCHHJJ-SKKKGAJSSA-N 0.000 description 1
- ZLYJLPBANUBMNI-UHFFFAOYSA-N 4-chloro-n-[(4-chlorophenyl)methyl]-5-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)-1,3-thiazol-2-amine Chemical compound S1C(CC=2C3=CC=CN=C3NC=2)=C(Cl)N=C1NCC1=CC=C(Cl)C=C1 ZLYJLPBANUBMNI-UHFFFAOYSA-N 0.000 description 1
- XALMRSUYUYROFH-UHFFFAOYSA-N 4-chloro-n-[5-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)pyridin-2-yl]benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NC(N=C1)=CC=C1CC1=CNC2=NC=CC=C12 XALMRSUYUYROFH-UHFFFAOYSA-N 0.000 description 1
- PKIFPNUTUQIALQ-UHFFFAOYSA-N 4-chloro-n-[[5-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)pyridin-2-yl]methyl]aniline Chemical compound C1=CC(Cl)=CC=C1NCC(N=C1)=CC=C1CC1=CNC2=NC=CC=C12 PKIFPNUTUQIALQ-UHFFFAOYSA-N 0.000 description 1
- FOCLOGXTKRVTKV-UHFFFAOYSA-N 4-fluoro-n-[5-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)pyridin-2-yl]benzamide Chemical compound C1=CC(F)=CC=C1C(=O)NC(N=C1)=CC=C1CC1=CNC2=NC=CC=C12 FOCLOGXTKRVTKV-UHFFFAOYSA-N 0.000 description 1
- ZJAFQAPHWPSKRZ-UHFFFAOYSA-N 4-nitrobenzenecarboperoxoic acid Chemical compound OOC(=O)C1=CC=C([N+]([O-])=O)C=C1 ZJAFQAPHWPSKRZ-UHFFFAOYSA-N 0.000 description 1
- HBKIQVFQUVRXSV-UHFFFAOYSA-N 5-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)-n-(thiophen-2-ylmethyl)pyridin-2-amine Chemical compound C=1C=C(CC=2C3=CC=CN=C3NC=2)C=NC=1NCC1=CC=CS1 HBKIQVFQUVRXSV-UHFFFAOYSA-N 0.000 description 1
- NODCQQSEMCESEC-UHFFFAOYSA-N 5-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)-n-[[4-(trifluoromethyl)phenyl]methyl]pyridin-2-amine Chemical compound C1=CC(C(F)(F)F)=CC=C1CNC(N=C1)=CC=C1CC1=CNC2=NC=CC=C12 NODCQQSEMCESEC-UHFFFAOYSA-N 0.000 description 1
- NAGBFAUCWPKZSU-UHFFFAOYSA-N 5-[(4-methoxy-1h-pyrrolo[2,3-b]pyridin-3-yl)methyl]-n-[[4-(trifluoromethyl)phenyl]methyl]pyridin-2-amine Chemical compound C1=2C(OC)=CC=NC=2NC=C1CC(C=N1)=CC=C1NCC1=CC=C(C(F)(F)F)C=C1 NAGBFAUCWPKZSU-UHFFFAOYSA-N 0.000 description 1
- YFVTZCWZAKUQTL-UHFFFAOYSA-N 5-[(5-bromo-1h-pyrrolo[2,3-b]pyridin-3-yl)methyl]-n-[(4-chlorophenyl)methyl]pyridin-2-amine Chemical compound C1=CC(Cl)=CC=C1CNC(N=C1)=CC=C1CC1=CNC2=NC=C(Br)C=C12 YFVTZCWZAKUQTL-UHFFFAOYSA-N 0.000 description 1
- MFXPJGJSKHZZGC-UHFFFAOYSA-N 5-[(5-chloro-1h-pyrrolo[2,3-b]pyridin-3-yl)methyl]-n-[[4-(trifluoromethyl)phenyl]methyl]pyridin-2-amine Chemical compound C1=CC(C(F)(F)F)=CC=C1CNC(N=C1)=CC=C1CC1=CNC2=NC=C(Cl)C=C12 MFXPJGJSKHZZGC-UHFFFAOYSA-N 0.000 description 1
- WLYQGNIWNGFGPH-UHFFFAOYSA-N 5-[(5-methoxy-1h-pyrrolo[2,3-b]pyridin-3-yl)methyl]-n-[[4-(trifluoromethyl)phenyl]methyl]pyridin-2-amine Chemical compound C12=CC(OC)=CN=C2NC=C1CC(C=N1)=CC=C1NCC1=CC=C(C(F)(F)F)C=C1 WLYQGNIWNGFGPH-UHFFFAOYSA-N 0.000 description 1
- FOGRODWURPXMFC-UHFFFAOYSA-N 5-[[5-(2-morpholin-4-ylethoxy)-1h-pyrrolo[2,3-b]pyridin-3-yl]methyl]-n-[[4-(trifluoromethyl)phenyl]methyl]pyridin-2-amine Chemical compound C1=CC(C(F)(F)F)=CC=C1CNC(N=C1)=CC=C1CC(C1=C2)=CNC1=NC=C2OCCN1CCOCC1 FOGRODWURPXMFC-UHFFFAOYSA-N 0.000 description 1
- JTPGSBKGXPGDIB-UHFFFAOYSA-N 5-[[5-(2-pyrrolidin-1-ylethoxy)-1h-pyrrolo[2,3-b]pyridin-3-yl]methyl]-n-[[4-(trifluoromethyl)phenyl]methyl]pyridin-2-amine Chemical compound C1=CC(C(F)(F)F)=CC=C1CNC(N=C1)=CC=C1CC(C1=C2)=CNC1=NC=C2OCCN1CCCC1 JTPGSBKGXPGDIB-UHFFFAOYSA-N 0.000 description 1
- ITDGTIJYDFPTTG-UHFFFAOYSA-N 5-[[5-[2-(diethylamino)ethoxy]-1h-pyrrolo[2,3-b]pyridin-3-yl]methyl]-n-[[4-(trifluoromethyl)phenyl]methyl]pyridin-2-amine Chemical compound C12=CC(OCCN(CC)CC)=CN=C2NC=C1CC(C=N1)=CC=C1NCC1=CC=C(C(F)(F)F)C=C1 ITDGTIJYDFPTTG-UHFFFAOYSA-N 0.000 description 1
- QBDAYDBVDKKBOE-UHFFFAOYSA-N 5-[[5-[3-(diethylamino)propoxy]-1h-pyrrolo[2,3-b]pyridin-3-yl]methyl]-n-[[4-(trifluoromethyl)phenyl]methyl]pyridin-2-amine Chemical compound C12=CC(OCCCN(CC)CC)=CN=C2NC=C1CC(C=N1)=CC=C1NCC1=CC=C(C(F)(F)F)C=C1 QBDAYDBVDKKBOE-UHFFFAOYSA-N 0.000 description 1
- ARDSPHDUGBPTGH-UHFFFAOYSA-N 5-[methoxy(1h-pyrrolo[2,3-b]pyridin-3-yl)methyl]-n-[[4-(trifluoromethyl)phenyl]methyl]pyridin-2-amine Chemical compound C=1NC2=NC=CC=C2C=1C(OC)C(C=N1)=CC=C1NCC1=CC=C(C(F)(F)F)C=C1 ARDSPHDUGBPTGH-UHFFFAOYSA-N 0.000 description 1
- JOFVXPMJWWQITK-UHFFFAOYSA-N 6-methoxy-5-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)-n-[[4-(trifluoromethyl)phenyl]methyl]pyridin-2-amine Chemical compound C=1C=C(CC=2C3=CC=CN=C3NC=2)C(OC)=NC=1NCC1=CC=C(C(F)(F)F)C=C1 JOFVXPMJWWQITK-UHFFFAOYSA-N 0.000 description 1
- MDFXRRISDIDORP-UHFFFAOYSA-N 6-methyl-5-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)-n-[[4-(trifluoromethyl)phenyl]methyl]pyridin-2-amine Chemical compound C=1C=C(CC=2C3=CC=CN=C3NC=2)C(C)=NC=1NCC1=CC=C(C(F)(F)F)C=C1 MDFXRRISDIDORP-UHFFFAOYSA-N 0.000 description 1
- YIUIVFFUEVPRIU-UHFFFAOYSA-N 8-chlorotheophylline Chemical class O=C1N(C)C(=O)N(C)C2=NC(Cl)=N[C]21 YIUIVFFUEVPRIU-UHFFFAOYSA-N 0.000 description 1
- 208000020053 Abnormal inflammatory response Diseases 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000701242 Adenoviridae Species 0.000 description 1
- 241001385733 Aesculus indica Species 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 102000002260 Alkaline Phosphatase Human genes 0.000 description 1
- 108020004774 Alkaline Phosphatase Proteins 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 108020005544 Antisense RNA Proteins 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- BMFMQGXDDJALKQ-BYPYZUCNSA-N Argininic acid Chemical compound NC(N)=NCCC[C@H](O)C(O)=O BMFMQGXDDJALKQ-BYPYZUCNSA-N 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- 208000032116 Autoimmune Experimental Encephalomyelitis Diseases 0.000 description 1
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 241000193830 Bacillus <bacterium> Species 0.000 description 1
- 244000063299 Bacillus subtilis Species 0.000 description 1
- 235000014469 Bacillus subtilis Nutrition 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000701412 Baculoviridae Species 0.000 description 1
- KUVIULQEHSCUHY-XYWKZLDCSA-N Beclometasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)COC(=O)CC)(OC(=O)CC)[C@@]1(C)C[C@@H]2O KUVIULQEHSCUHY-XYWKZLDCSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 208000006386 Bone Resorption Diseases 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 230000005653 Brownian motion process Effects 0.000 description 1
- VOVIALXJUBGFJZ-KWVAZRHASA-N Budesonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(CCC)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O VOVIALXJUBGFJZ-KWVAZRHASA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- 102100021943 C-C motif chemokine 2 Human genes 0.000 description 1
- 101710155857 C-C motif chemokine 2 Proteins 0.000 description 1
- 229940124204 C-kit inhibitor Drugs 0.000 description 1
- JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 1
- 101710132601 Capsid protein Proteins 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 241000701489 Cauliflower mosaic virus Species 0.000 description 1
- 102000019034 Chemokines Human genes 0.000 description 1
- 108010012236 Chemokines Proteins 0.000 description 1
- 108010000659 Choline oxidase Proteins 0.000 description 1
- 206010008805 Chromosomal abnormalities Diseases 0.000 description 1
- 208000031404 Chromosome Aberrations Diseases 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 101710094648 Coat protein Proteins 0.000 description 1
- 208000032170 Congenital Abnormalities Diseases 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- AAWZDTNXLSGCEK-UHFFFAOYSA-N Cordycepinsaeure Natural products OC1CC(O)(C(O)=O)CC(O)C1O AAWZDTNXLSGCEK-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 241000450599 DNA viruses Species 0.000 description 1
- 206010061619 Deformity Diseases 0.000 description 1
- 108010053770 Deoxyribonucleases Proteins 0.000 description 1
- 102000016911 Deoxyribonucleases Human genes 0.000 description 1
- 241000255581 Drosophila <fruit fly, genus> Species 0.000 description 1
- 206010058314 Dysplasia Diseases 0.000 description 1
- 238000002965 ELISA Methods 0.000 description 1
- 102100023688 Eotaxin Human genes 0.000 description 1
- 101710139422 Eotaxin Proteins 0.000 description 1
- 241000701959 Escherichia virus Lambda Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 108010074860 Factor Xa Proteins 0.000 description 1
- 241000714174 Feline sarcoma virus Species 0.000 description 1
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 1
- 241000713813 Gibbon ape leukemia virus Species 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 102100021181 Golgi phosphoprotein 3 Human genes 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 239000012981 Hank's balanced salt solution Substances 0.000 description 1
- 108010001336 Horseradish Peroxidase Proteins 0.000 description 1
- 101100321817 Human parvovirus B19 (strain HV) 7.5K gene Proteins 0.000 description 1
- 108010064593 Intercellular Adhesion Molecule-1 Proteins 0.000 description 1
- 102100037877 Intercellular adhesion molecule 1 Human genes 0.000 description 1
- 108090000193 Interleukin-1 beta Proteins 0.000 description 1
- 102000010789 Interleukin-2 Receptors Human genes 0.000 description 1
- 108010038453 Interleukin-2 Receptors Proteins 0.000 description 1
- 102100020880 Kit ligand Human genes 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 102000004856 Lectins Human genes 0.000 description 1
- 108090001090 Lectins Proteins 0.000 description 1
- 102000004895 Lipoproteins Human genes 0.000 description 1
- 108090001030 Lipoproteins Proteins 0.000 description 1
- 239000012448 Lithium borohydride Substances 0.000 description 1
- 208000028018 Lymphocytic leukaemia Diseases 0.000 description 1
- 101710125418 Major capsid protein Proteins 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 208000035268 Mast Cell Activation disease Diseases 0.000 description 1
- 102100027754 Mast/stem cell growth factor receptor Kit Human genes 0.000 description 1
- 102000018697 Membrane Proteins Human genes 0.000 description 1
- 108010052285 Membrane Proteins Proteins 0.000 description 1
- 108010006035 Metalloproteases Proteins 0.000 description 1
- 102000005741 Metalloproteases Human genes 0.000 description 1
- 102000010750 Metalloproteins Human genes 0.000 description 1
- 108010063312 Metalloproteins Proteins 0.000 description 1
- 102000003792 Metallothionein Human genes 0.000 description 1
- 108090000157 Metallothionein Proteins 0.000 description 1
- 101150101095 Mmp12 gene Proteins 0.000 description 1
- 102000015728 Mucins Human genes 0.000 description 1
- 108010063954 Mucins Proteins 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 101500024170 Mus musculus Adrenomedullin Proteins 0.000 description 1
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 description 1
- 208000033833 Myelomonocytic Chronic Leukemia Diseases 0.000 description 1
- HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 108091061960 Naked DNA Proteins 0.000 description 1
- 102100021850 Nardilysin Human genes 0.000 description 1
- 108090000970 Nardilysin Proteins 0.000 description 1
- 229930193140 Neomycin Natural products 0.000 description 1
- 206010061309 Neoplasm progression Diseases 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 108020004711 Nucleic Acid Probes Proteins 0.000 description 1
- 108700020497 Nucleopolyhedrovirus polyhedrin Proteins 0.000 description 1
- 101710141454 Nucleoprotein Proteins 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 102000043276 Oncogene Human genes 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 101000909992 Papio hamadryas Chymase Proteins 0.000 description 1
- 208000030852 Parasitic disease Diseases 0.000 description 1
- 241000701945 Parvoviridae Species 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 206010057249 Phagocytosis Diseases 0.000 description 1
- 241000286209 Phasianidae Species 0.000 description 1
- 102000004160 Phosphoric Monoester Hydrolases Human genes 0.000 description 1
- 108090000608 Phosphoric Monoester Hydrolases Proteins 0.000 description 1
- 241000709664 Picornaviridae Species 0.000 description 1
- 102000018967 Platelet-Derived Growth Factor beta Receptor Human genes 0.000 description 1
- 108010051742 Platelet-Derived Growth Factor beta Receptor Proteins 0.000 description 1
- 206010035664 Pneumonia Diseases 0.000 description 1
- 241001505332 Polyomavirus sp. Species 0.000 description 1
- 241000700625 Poxviridae Species 0.000 description 1
- 101710083689 Probable capsid protein Proteins 0.000 description 1
- 101710093543 Probable non-specific lipid-transfer protein Proteins 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 102000052575 Proto-Oncogene Human genes 0.000 description 1
- 108700020978 Proto-Oncogene Proteins 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- AAWZDTNXLSGCEK-ZHQZDSKASA-N Quinic acid Natural products O[C@H]1CC(O)(C(O)=O)C[C@H](O)C1O AAWZDTNXLSGCEK-ZHQZDSKASA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 102000004278 Receptor Protein-Tyrosine Kinases Human genes 0.000 description 1
- 108090000873 Receptor Protein-Tyrosine Kinases Proteins 0.000 description 1
- 108700025701 Retinoblastoma Genes Proteins 0.000 description 1
- 108010003581 Ribulose-bisphosphate carboxylase Proteins 0.000 description 1
- 241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 description 1
- GIIZNNXWQWCKIB-UHFFFAOYSA-N Serevent Chemical compound C1=C(O)C(CO)=CC(C(O)CNCCCCCCOCCCCC=2C=CC=CC=2)=C1 GIIZNNXWQWCKIB-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 108020004459 Small interfering RNA Proteins 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 102000011971 Sphingomyelin Phosphodiesterase Human genes 0.000 description 1
- 108010061312 Sphingomyelin Phosphodiesterase Proteins 0.000 description 1
- 241000256248 Spodoptera Species 0.000 description 1
- 108010090804 Streptavidin Proteins 0.000 description 1
- 241000187747 Streptomyces Species 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 1
- 210000001744 T-lymphocyte Anatomy 0.000 description 1
- 239000004098 Tetracycline Substances 0.000 description 1
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 description 1
- 102100036407 Thioredoxin Human genes 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 108700009124 Transcription Initiation Site Proteins 0.000 description 1
- 108091023040 Transcription factor Proteins 0.000 description 1
- 102000040945 Transcription factor Human genes 0.000 description 1
- 102100040247 Tumor necrosis factor Human genes 0.000 description 1
- 208000004608 Ureteral Obstruction Diseases 0.000 description 1
- 208000024780 Urticaria Diseases 0.000 description 1
- 241000700618 Vaccinia virus Species 0.000 description 1
- 206010046865 Vaccinia virus infection Diseases 0.000 description 1
- 108010000134 Vascular Cell Adhesion Molecule-1 Proteins 0.000 description 1
- 102100023543 Vascular cell adhesion protein 1 Human genes 0.000 description 1
- 206010047115 Vasculitis Diseases 0.000 description 1
- 241000251539 Vertebrata <Metazoa> Species 0.000 description 1
- 108020005202 Viral DNA Proteins 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- CTGQFDUGZJEEEK-UHFFFAOYSA-N [2,6-bis[(4-chlorophenyl)methylamino]pyridin-3-yl]-(1h-pyrrolo[2,3-b]pyridin-3-yl)methanone Chemical compound C1=CC(Cl)=CC=C1CNC(N=C1NCC=2C=CC(Cl)=CC=2)=CC=C1C(=O)C1=CNC2=NC=CC=C12 CTGQFDUGZJEEEK-UHFFFAOYSA-N 0.000 description 1
- UIUPMGRZDIENNV-UHFFFAOYSA-N [2-[(4-chlorophenyl)methylamino]-1,3-thiazol-5-yl]-(1h-pyrrolo[2,3-b]pyridin-3-yl)methanone Chemical compound C1=CC(Cl)=CC=C1CNC1=NC=C(C(=O)C=2C3=CC=CN=C3NC=2)S1 UIUPMGRZDIENNV-UHFFFAOYSA-N 0.000 description 1
- SSAZEXZQWNHGFZ-UHFFFAOYSA-N [2-chloro-6-[(4-chlorophenyl)methylamino]pyridin-3-yl]-(1h-pyrrolo[2,3-b]pyridin-3-yl)methanol Chemical compound C=1NC2=NC=CC=C2C=1C(O)C(C(=N1)Cl)=CC=C1NCC1=CC=C(Cl)C=C1 SSAZEXZQWNHGFZ-UHFFFAOYSA-N 0.000 description 1
- JLJGYMRLPCIGIM-UHFFFAOYSA-N [2-chloro-6-[(4-chlorophenyl)methylamino]pyridin-3-yl]-(1h-pyrrolo[2,3-b]pyridin-3-yl)methanone Chemical compound C1=CC(Cl)=CC=C1CNC(N=C1Cl)=CC=C1C(=O)C1=CNC2=NC=CC=C12 JLJGYMRLPCIGIM-UHFFFAOYSA-N 0.000 description 1
- OFXAHYUHQHTWKK-UHFFFAOYSA-N [3,5-dimethyl-4-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)pyrazol-1-yl]-phenylmethanone Chemical compound CC1=C(CC=2C3=CC=CN=C3NC=2)C(C)=NN1C(=O)C1=CC=CC=C1 OFXAHYUHQHTWKK-UHFFFAOYSA-N 0.000 description 1
- UPHBGKHSEUGMKD-UHFFFAOYSA-N [3-[(6-chloropyridin-3-yl)methyl]pyrrolo[2,3-b]pyridin-1-yl]-tri(propan-2-yl)silane Chemical compound C12=CC=CN=C2N([Si](C(C)C)(C(C)C)C(C)C)C=C1CC1=CC=C(Cl)N=C1 UPHBGKHSEUGMKD-UHFFFAOYSA-N 0.000 description 1
- CVWIZWZUQKVHBX-UHFFFAOYSA-N [6-(2-methylpropylamino)pyridin-3-yl]-(1h-pyrrolo[2,3-b]pyridin-3-yl)methanol Chemical compound C1=NC(NCC(C)C)=CC=C1C(O)C1=CNC2=NC=CC=C12 CVWIZWZUQKVHBX-UHFFFAOYSA-N 0.000 description 1
- ZVPVHALFSGBBDF-UHFFFAOYSA-N [6-(2-methylpropylamino)pyridin-3-yl]-(1h-pyrrolo[2,3-b]pyridin-3-yl)methanone Chemical compound C1=NC(NCC(C)C)=CC=C1C(=O)C1=CNC2=NC=CC=C12 ZVPVHALFSGBBDF-UHFFFAOYSA-N 0.000 description 1
- SRKZHXMZVWFSDG-UHFFFAOYSA-N [6-(3-hydroxyanilino)pyridin-3-yl]-(1h-pyrrolo[2,3-b]pyridin-3-yl)methanone Chemical compound OC1=CC=CC(NC=2N=CC(=CC=2)C(=O)C=2C3=CC=CN=C3NC=2)=C1 SRKZHXMZVWFSDG-UHFFFAOYSA-N 0.000 description 1
- NTMBHJWRCDRUJR-UHFFFAOYSA-N [6-(3-phenylmethoxyanilino)pyridin-3-yl]-(1h-pyrrolo[2,3-b]pyridin-3-yl)methanone Chemical compound C=1NC2=NC=CC=C2C=1C(=O)C(C=N1)=CC=C1NC(C=1)=CC=CC=1OCC1=CC=CC=C1 NTMBHJWRCDRUJR-UHFFFAOYSA-N 0.000 description 1
- WSKNCAQFPMBDMH-UHFFFAOYSA-N [6-(benzylamino)pyridin-3-yl]-(1h-pyrrolo[2,3-b]pyridin-3-yl)methanone Chemical compound C=1NC2=NC=CC=C2C=1C(=O)C(C=N1)=CC=C1NCC1=CC=CC=C1 WSKNCAQFPMBDMH-UHFFFAOYSA-N 0.000 description 1
- UWUYUCBINMRJFD-UHFFFAOYSA-N [6-(cyclohexylmethylamino)pyridin-3-yl]-(1h-pyrrolo[2,3-b]pyridin-3-yl)methanone Chemical compound C=1NC2=NC=CC=C2C=1C(=O)C(C=N1)=CC=C1NCC1CCCCC1 UWUYUCBINMRJFD-UHFFFAOYSA-N 0.000 description 1
- SMEAINNADGIOLR-UHFFFAOYSA-N [6-(cyclopropylmethylamino)pyridin-3-yl]-(1h-pyrrolo[2,3-b]pyridin-3-yl)methanol Chemical compound C=1NC2=NC=CC=C2C=1C(O)C(C=N1)=CC=C1NCC1CC1 SMEAINNADGIOLR-UHFFFAOYSA-N 0.000 description 1
- HAOSZXVMWPJDGK-UHFFFAOYSA-N [6-(cyclopropylmethylamino)pyridin-3-yl]-(1h-pyrrolo[2,3-b]pyridin-3-yl)methanone Chemical compound C=1NC2=NC=CC=C2C=1C(=O)C(C=N1)=CC=C1NCC1CC1 HAOSZXVMWPJDGK-UHFFFAOYSA-N 0.000 description 1
- KVMRZAFFARYSSQ-UHFFFAOYSA-N [6-(propan-2-ylamino)pyridin-3-yl]-(1h-pyrrolo[2,3-b]pyridin-3-yl)methanone Chemical compound C1=NC(NC(C)C)=CC=C1C(=O)C1=CNC2=NC=CC=C12 KVMRZAFFARYSSQ-UHFFFAOYSA-N 0.000 description 1
- WHRLNYSHMVBIKV-UHFFFAOYSA-N [6-[(3-fluorophenyl)methylamino]pyridin-3-yl]-(1h-pyrrolo[2,3-b]pyridin-3-yl)methanone Chemical compound FC1=CC=CC(CNC=2N=CC(=CC=2)C(=O)C=2C3=CC=CN=C3NC=2)=C1 WHRLNYSHMVBIKV-UHFFFAOYSA-N 0.000 description 1
- KDQBAAWQAOFJIB-UHFFFAOYSA-N [6-[(4-chlorophenyl)methylamino]-2-(trifluoromethyl)pyridin-3-yl]-(1h-pyrrolo[2,3-b]pyridin-3-yl)methanone Chemical compound C=1C=C(C(=O)C=2C3=CC=CN=C3NC=2)C(C(F)(F)F)=NC=1NCC1=CC=C(Cl)C=C1 KDQBAAWQAOFJIB-UHFFFAOYSA-N 0.000 description 1
- YXROAARZIUSQQT-UHFFFAOYSA-N [6-[(4-chlorophenyl)methylamino]-2-methylpyridin-3-yl]-(1h-pyrrolo[2,3-b]pyridin-3-yl)methanol Chemical compound C=1C=C(C(O)C=2C3=CC=CN=C3NC=2)C(C)=NC=1NCC1=CC=C(Cl)C=C1 YXROAARZIUSQQT-UHFFFAOYSA-N 0.000 description 1
- NGJSMFFFKADTHZ-UHFFFAOYSA-N [6-[(4-chlorophenyl)methylamino]pyridin-3-yl]-(1h-pyrrolo[2,3-b]pyridin-3-yl)methanol Chemical compound C=1NC2=NC=CC=C2C=1C(O)C(C=N1)=CC=C1NCC1=CC=C(Cl)C=C1 NGJSMFFFKADTHZ-UHFFFAOYSA-N 0.000 description 1
- BXBMGHCPAWQMEC-UHFFFAOYSA-N [6-[(4-fluorophenyl)methylamino]pyridin-3-yl]-(1h-pyrrolo[2,3-b]pyridin-3-yl)methanone Chemical compound C1=CC(F)=CC=C1CNC1=CC=C(C(=O)C=2C3=CC=CN=C3NC=2)C=N1 BXBMGHCPAWQMEC-UHFFFAOYSA-N 0.000 description 1
- CKUAXEQHGKSLHN-UHFFFAOYSA-N [C].[N] Chemical compound [C].[N] CKUAXEQHGKSLHN-UHFFFAOYSA-N 0.000 description 1
- 230000005856 abnormality Effects 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
- 229940022663 acetate Drugs 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 108700010877 adenoviridae proteins Proteins 0.000 description 1
- 210000001789 adipocyte Anatomy 0.000 description 1
- 210000000577 adipose tissue Anatomy 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 238000001261 affinity purification Methods 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- IAJILQKETJEXLJ-QTBDOELSSA-N aldehydo-D-glucuronic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-QTBDOELSSA-N 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
- 229940061720 alpha hydroxy acid Drugs 0.000 description 1
- 150000001280 alpha hydroxy acids Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 238000003016 alphascreen Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 229960000723 ampicillin Drugs 0.000 description 1
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 238000005571 anion exchange chromatography Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 229940065524 anticholinergics inhalants for obstructive airway diseases Drugs 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 230000002917 arthritic effect Effects 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- 239000000305 astragalus gummifer gum Substances 0.000 description 1
- 210000001130 astrocyte Anatomy 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 description 1
- 210000003719 b-lymphocyte Anatomy 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 229950000210 beclometasone dipropionate Drugs 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229940125388 beta agonist Drugs 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- 239000003833 bile salt Substances 0.000 description 1
- 229940093761 bile salts Drugs 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 238000002306 biochemical method Methods 0.000 description 1
- 229920001222 biopolymer Polymers 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 210000004271 bone marrow stromal cell Anatomy 0.000 description 1
- 230000024279 bone resorption Effects 0.000 description 1
- MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 1
- UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 210000005013 brain tissue Anatomy 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-M bromate Inorganic materials [O-]Br(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-M 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 238000005537 brownian motion Methods 0.000 description 1
- 229960004436 budesonide Drugs 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000000337 buffer salt Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 238000005251 capillar electrophoresis Methods 0.000 description 1
- 210000000234 capsid Anatomy 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000005277 cation exchange chromatography Methods 0.000 description 1
- 230000001364 causal effect Effects 0.000 description 1
- 230000022131 cell cycle Effects 0.000 description 1
- 230000010001 cellular homeostasis Effects 0.000 description 1
- 201000007455 central nervous system cancer Diseases 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000005482 chemotactic factor Substances 0.000 description 1
- 230000035605 chemotaxis Effects 0.000 description 1
- 229940044683 chemotherapy drug Drugs 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 description 1
- 229930002868 chlorophyll a Natural products 0.000 description 1
- NSMUHPMZFPKNMZ-VBYMZDBQSA-M chlorophyll b Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C=O)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 NSMUHPMZFPKNMZ-VBYMZDBQSA-M 0.000 description 1
- 229930002869 chlorophyll b Natural products 0.000 description 1
- VDANGULDQQJODZ-UHFFFAOYSA-N chloroprocaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1Cl VDANGULDQQJODZ-UHFFFAOYSA-N 0.000 description 1
- 229960002023 chloroprocaine Drugs 0.000 description 1
- 229960003677 chloroquine Drugs 0.000 description 1
- WHTVZRBIWZFKQO-UHFFFAOYSA-N chloroquine Natural products ClC1=CC=C2C(NC(C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-UHFFFAOYSA-N 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 229940117975 chromium trioxide Drugs 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 1
- 230000006020 chronic inflammation Effects 0.000 description 1
- 201000010902 chronic myelomonocytic leukemia Diseases 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 229940001468 citrate Drugs 0.000 description 1
- 230000009668 clonal growth Effects 0.000 description 1
- 230000004186 co-expression Effects 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 208000029742 colonic neoplasm Diseases 0.000 description 1
- 230000005757 colony formation Effects 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 239000003184 complementary RNA Substances 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 230000006552 constitutive activation Effects 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 229940099112 cornstarch Drugs 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000000287 crude extract Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000002993 cycloalkylene group Chemical group 0.000 description 1
- 229940097362 cyclodextrins Drugs 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 description 1
- 230000016396 cytokine production Effects 0.000 description 1
- 230000001461 cytolytic effect Effects 0.000 description 1
- 210000000805 cytoplasm Anatomy 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000005695 dehalogenation reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 238000002405 diagnostic procedure Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 229940043237 diethanolamine Drugs 0.000 description 1
- 210000002249 digestive system Anatomy 0.000 description 1
- 125000004598 dihydrobenzofuryl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 description 1
- OZRNSSUDZOLUSN-LBPRGKRZSA-N dihydrofolic acid Chemical compound N=1C=2C(=O)NC(N)=NC=2NCC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OZRNSSUDZOLUSN-LBPRGKRZSA-N 0.000 description 1
- 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000004655 dihydropyridinyl group Chemical group N1(CC=CC=C1)* 0.000 description 1
- 229960004993 dimenhydrinate Drugs 0.000 description 1
- FRTGEIHSCHXMTI-UHFFFAOYSA-N dimethyl octanediimidate Chemical compound COC(=N)CCCCCCC(=N)OC FRTGEIHSCHXMTI-UHFFFAOYSA-N 0.000 description 1
- 230000003467 diminishing effect Effects 0.000 description 1
- 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 description 1
- 235000021186 dishes Nutrition 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000003828 downregulation Effects 0.000 description 1
- 230000007783 downstream signaling Effects 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 229940099182 dramamine Drugs 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 238000009509 drug development Methods 0.000 description 1
- 239000013583 drug formulation Substances 0.000 description 1
- 241001493065 dsRNA viruses Species 0.000 description 1
- 229940125436 dual inhibitor Drugs 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 238000001962 electrophoresis Methods 0.000 description 1
- 238000004520 electroporation Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000013020 embryo development Effects 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 201000002491 encephalomyelitis Diseases 0.000 description 1
- 210000003038 endothelium Anatomy 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 239000003248 enzyme activator Substances 0.000 description 1
- 239000002532 enzyme inhibitor Substances 0.000 description 1
- 102000006966 enzyme regulator activity proteins Human genes 0.000 description 1
- 108040000578 enzyme regulator activity proteins Proteins 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 229940011871 estrogen Drugs 0.000 description 1
- 239000000262 estrogen Substances 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical class CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 229940012017 ethylenediamine Drugs 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000013401 experimental design Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000010685 fatty oil Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 230000003352 fibrogenic effect Effects 0.000 description 1
- 230000003176 fibrotic effect Effects 0.000 description 1
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 108091006047 fluorescent proteins Proteins 0.000 description 1
- 102000034287 fluorescent proteins Human genes 0.000 description 1
- WMWTYOKRWGGJOA-CENSZEJFSA-N fluticasone propionate Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)SCF)(OC(=O)CC)[C@@]2(C)C[C@@H]1O WMWTYOKRWGGJOA-CENSZEJFSA-N 0.000 description 1
- 229960000289 fluticasone propionate Drugs 0.000 description 1
- 108700024553 fms Genes Proteins 0.000 description 1
- 229960002598 fumaric acid Drugs 0.000 description 1
- 238000010230 functional analysis Methods 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- IECPWNUMDGFDKC-MZJAQBGESA-N fusidic acid Chemical class O[C@@H]([C@@H]12)C[C@H]3\C(=C(/CCC=C(C)C)C(O)=O)[C@@H](OC(C)=O)C[C@]3(C)[C@@]2(C)CC[C@@H]2[C@]1(C)CC[C@@H](O)[C@H]2C IECPWNUMDGFDKC-MZJAQBGESA-N 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000001502 gel electrophoresis Methods 0.000 description 1
- 239000007897 gelcap Substances 0.000 description 1
- 230000004545 gene duplication Effects 0.000 description 1
- 238000001415 gene therapy Methods 0.000 description 1
- 238000010353 genetic engineering Methods 0.000 description 1
- 230000001434 glomerular Effects 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229940097043 glucuronic acid Drugs 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 229960004275 glycolic acid Drugs 0.000 description 1
- 102000035122 glycosylated proteins Human genes 0.000 description 1
- 108091005608 glycosylated proteins Proteins 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 208000010758 granulomatous inflammation Diseases 0.000 description 1
- 210000002503 granulosa cell Anatomy 0.000 description 1
- 208000035474 group of disease Diseases 0.000 description 1
- 208000014951 hematologic disease Diseases 0.000 description 1
- 125000006588 heterocycloalkylene group Chemical group 0.000 description 1
- 238000012188 high-throughput screening assay Methods 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 210000000688 human artificial chromosome Anatomy 0.000 description 1
- 210000005260 human cell Anatomy 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000004191 hydrophobic interaction chromatography Methods 0.000 description 1
- 229910052588 hydroxylapatite Inorganic materials 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- HIFJCPQKFCZDDL-ACWOEMLNSA-N iloprost Chemical compound C1\C(=C/CCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)C(C)CC#CC)[C@H](O)C[C@@H]21 HIFJCPQKFCZDDL-ACWOEMLNSA-N 0.000 description 1
- 229960002240 iloprost Drugs 0.000 description 1
- 230000008076 immune mechanism Effects 0.000 description 1
- 230000000951 immunodiffusion Effects 0.000 description 1
- 238000000760 immunoelectrophoresis Methods 0.000 description 1
- 238000010166 immunofluorescence Methods 0.000 description 1
- 230000002163 immunogen Effects 0.000 description 1
- 229940072221 immunoglobulins Drugs 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 210000004969 inflammatory cell Anatomy 0.000 description 1
- 230000028709 inflammatory response Effects 0.000 description 1
- 238000002664 inhalation therapy Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 238000012482 interaction analysis Methods 0.000 description 1
- 210000002490 intestinal epithelial cell Anatomy 0.000 description 1
- 208000003243 intestinal obstruction Diseases 0.000 description 1
- 210000001596 intra-abdominal fat Anatomy 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 238000007917 intracranial administration Methods 0.000 description 1
- 210000005024 intraepithelial lymphocyte Anatomy 0.000 description 1
- 230000009545 invasion Effects 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 238000000021 kinase assay Methods 0.000 description 1
- 238000011005 laboratory method Methods 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 229940001447 lactate Drugs 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 description 1
- 239000002523 lectin Substances 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- VNYSSYRCGWBHLG-AMOLWHMGSA-N leukotriene B4 Chemical compound CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O VNYSSYRCGWBHLG-AMOLWHMGSA-N 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 230000037356 lipid metabolism Effects 0.000 description 1
- 238000001638 lipofection Methods 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 210000002751 lymph Anatomy 0.000 description 1
- 208000003747 lymphoid leukemia Diseases 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- USSBDBZGEDUBHE-UHFFFAOYSA-L magnesium;2-oxidooxycarbonylbenzoate Chemical compound [Mg+2].[O-]OC(=O)C1=CC=CC=C1C([O-])=O USSBDBZGEDUBHE-UHFFFAOYSA-L 0.000 description 1
- 210000003794 male germ cell Anatomy 0.000 description 1
- 229940098895 maleic acid Drugs 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 230000032123 mast cell apoptotic process Effects 0.000 description 1
- 208000000516 mast-cell leukemia Diseases 0.000 description 1
- 238000002483 medication Methods 0.000 description 1
- 229960003194 meglumine Drugs 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000009245 menopause Effects 0.000 description 1
- 201000008806 mesenchymal cell neoplasm Diseases 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 208000037819 metastatic cancer Diseases 0.000 description 1
- 208000011575 metastatic malignant neoplasm Diseases 0.000 description 1
- TWXDDNPPQUTEOV-FVGYRXGTSA-N methamphetamine hydrochloride Chemical compound Cl.CN[C@@H](C)CC1=CC=CC=C1 TWXDDNPPQUTEOV-FVGYRXGTSA-N 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 229960002900 methylcellulose Drugs 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 238000002493 microarray Methods 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- ZAHQPTJLOCWVPG-UHFFFAOYSA-N mitoxantrone dihydrochloride Chemical compound Cl.Cl.O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO ZAHQPTJLOCWVPG-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000002062 molecular scaffold Substances 0.000 description 1
- WOFMFGQZHJDGCX-ZULDAHANSA-N mometasone furoate Chemical compound O([C@]1([C@@]2(C)C[C@H](O)[C@]3(Cl)[C@@]4(C)C=CC(=O)C=C4CC[C@H]3[C@@H]2C[C@H]1C)C(=O)CCl)C(=O)C1=CC=CO1 WOFMFGQZHJDGCX-ZULDAHANSA-N 0.000 description 1
- 229960002744 mometasone furoate Drugs 0.000 description 1
- 229940051875 mucins Drugs 0.000 description 1
- 210000004877 mucosa Anatomy 0.000 description 1
- 238000002703 mutagenesis Methods 0.000 description 1
- 231100000350 mutagenesis Toxicity 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- DNVBPMJCOORCQH-UHFFFAOYSA-N n,n-dimethyl-1-[1-tri(propan-2-yl)silylpyrrolo[2,3-b]pyridin-3-yl]methanamine Chemical compound C1=CN=C2N([Si](C(C)C)(C(C)C)C(C)C)C=C(CN(C)C)C2=C1 DNVBPMJCOORCQH-UHFFFAOYSA-N 0.000 description 1
- JRWMWZPRBRJDEZ-UHFFFAOYSA-N n,n-dimethyl-5-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)pyridin-2-amine Chemical compound C1=NC(N(C)C)=CC=C1CC1=CNC2=NC=CC=C12 JRWMWZPRBRJDEZ-UHFFFAOYSA-N 0.000 description 1
- JLFAZFMFWGLOSU-UHFFFAOYSA-N n-(2-methylpropyl)-5-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)pyridin-2-amine Chemical compound C1=NC(NCC(C)C)=CC=C1CC1=CNC2=NC=CC=C12 JLFAZFMFWGLOSU-UHFFFAOYSA-N 0.000 description 1
- YTQYWHACOBRAQQ-UHFFFAOYSA-N n-(4-chlorophenyl)-5-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)pyridine-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)C(N=C1)=CC=C1CC1=CNC2=NC=CC=C12 YTQYWHACOBRAQQ-UHFFFAOYSA-N 0.000 description 1
- YHEMCOKAAPCXCT-UHFFFAOYSA-N n-(cyclohexylmethyl)-5-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)pyridin-2-amine Chemical compound C=1C=C(CC=2C3=CC=CN=C3NC=2)C=NC=1NCC1CCCCC1 YHEMCOKAAPCXCT-UHFFFAOYSA-N 0.000 description 1
- AXLNNBVKDGTODY-UHFFFAOYSA-N n-(cyclopropylmethyl)-5-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)pyridin-2-amine Chemical compound C=1C=C(CC=2C3=CC=CN=C3NC=2)C=NC=1NCC1CC1 AXLNNBVKDGTODY-UHFFFAOYSA-N 0.000 description 1
- WPZIAXPZFFSUPT-AWEZNQCLSA-N n-[(1s)-1-(4-chlorophenyl)ethyl]-5-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)pyridin-2-amine Chemical compound C1([C@@H](NC=2N=CC(CC=3C4=CC=CN=C4NC=3)=CC=2)C)=CC=C(Cl)C=C1 WPZIAXPZFFSUPT-AWEZNQCLSA-N 0.000 description 1
- AMDMKMUQDNWBOJ-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-5-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)pyridin-2-amine Chemical compound C1=CC(Cl)=CC=C1CNC(N=C1)=CC=C1CC1=CNC2=NC=CC=C12 AMDMKMUQDNWBOJ-UHFFFAOYSA-N 0.000 description 1
- CFNHTCBRPUVHQZ-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-5-[(4-chloro-1h-pyrrolo[2,3-b]pyridin-3-yl)methyl]pyridin-2-amine Chemical compound C1=CC(Cl)=CC=C1CNC(N=C1)=CC=C1CC1=CNC2=NC=CC(Cl)=C12 CFNHTCBRPUVHQZ-UHFFFAOYSA-N 0.000 description 1
- QGJIXSHXPRXTBY-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-5-[(4-methoxy-1h-pyrrolo[2,3-b]pyridin-3-yl)methyl]pyridin-2-amine Chemical compound C1=2C(OC)=CC=NC=2NC=C1CC(C=N1)=CC=C1NCC1=CC=C(Cl)C=C1 QGJIXSHXPRXTBY-UHFFFAOYSA-N 0.000 description 1
- HRUMOTVJNCYSDH-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-5-[(5-chloro-1h-pyrrolo[2,3-b]pyridin-3-yl)methyl]pyridin-2-amine Chemical compound C1=CC(Cl)=CC=C1CNC(N=C1)=CC=C1CC1=CNC2=NC=C(Cl)C=C12 HRUMOTVJNCYSDH-UHFFFAOYSA-N 0.000 description 1
- YAUYBNWEUZOZJY-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-5-[(5-methoxy-1h-pyrrolo[2,3-b]pyridin-3-yl)methyl]pyridin-2-amine Chemical compound C12=CC(OC)=CN=C2NC=C1CC(C=N1)=CC=C1NCC1=CC=C(Cl)C=C1 YAUYBNWEUZOZJY-UHFFFAOYSA-N 0.000 description 1
- WOOAKMGJPQNFKY-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-5-[[5-(2-morpholin-4-ylethoxy)-1h-pyrrolo[2,3-b]pyridin-3-yl]methyl]pyridin-2-amine Chemical compound C1=CC(Cl)=CC=C1CNC(N=C1)=CC=C1CC(C1=C2)=CNC1=NC=C2OCCN1CCOCC1 WOOAKMGJPQNFKY-UHFFFAOYSA-N 0.000 description 1
- RSGCWNJJAYMDQF-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-5-[methoxy(1h-pyrrolo[2,3-b]pyridin-3-yl)methyl]pyridin-2-amine Chemical compound C=1NC2=NC=CC=C2C=1C(OC)C(C=N1)=CC=C1NCC1=CC=C(Cl)C=C1 RSGCWNJJAYMDQF-UHFFFAOYSA-N 0.000 description 1
- QUVRSDDDSBYBRO-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-5-[methoxy-(5-pyridin-3-yl-1h-pyrrolo[2,3-b]pyridin-3-yl)methyl]pyridin-2-amine Chemical compound C=1C=C(NCC=2C=CC(Cl)=CC=2)N=CC=1C(OC)C(C1=C2)=CNC1=NC=C2C1=CC=CN=C1 QUVRSDDDSBYBRO-UHFFFAOYSA-N 0.000 description 1
- RXIFNDTWDSHALG-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-5-[methoxy-[5-(3-methylsulfonylphenyl)-1h-pyrrolo[2,3-b]pyridin-3-yl]methyl]pyridin-2-amine Chemical compound C=1C=C(NCC=2C=CC(Cl)=CC=2)N=CC=1C(OC)C(C1=C2)=CNC1=NC=C2C1=CC=CC(S(C)(=O)=O)=C1 RXIFNDTWDSHALG-UHFFFAOYSA-N 0.000 description 1
- RLSAABSTMBRMOO-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-6-fluoro-5-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)pyridin-2-amine Chemical compound C=1C=C(CC=2C3=CC=CN=C3NC=2)C(F)=NC=1NCC1=CC=C(Cl)C=C1 RLSAABSTMBRMOO-UHFFFAOYSA-N 0.000 description 1
- XXYSCOULUBJPKB-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-6-methoxy-5-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)pyridin-2-amine Chemical compound C=1C=C(CC=2C3=CC=CN=C3NC=2)C(OC)=NC=1NCC1=CC=C(Cl)C=C1 XXYSCOULUBJPKB-UHFFFAOYSA-N 0.000 description 1
- YJFZGTIZGFIXSC-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-6-methyl-5-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)pyridin-2-amine Chemical compound C=1C=C(CC=2C3=CC=CN=C3NC=2)C(C)=NC=1NCC1=CC=C(Cl)C=C1 YJFZGTIZGFIXSC-UHFFFAOYSA-N 0.000 description 1
- DVMGTZRHKQYIBK-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-5-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)pyridin-2-amine Chemical compound C1=CC(F)=CC=C1CNC(N=C1)=CC=C1CC1=CNC2=NC=CC=C12 DVMGTZRHKQYIBK-UHFFFAOYSA-N 0.000 description 1
- NWQSQTFZPMDFOJ-UHFFFAOYSA-N n-[(4-methoxyphenyl)methyl]-5-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)pyridin-2-amine Chemical compound C1=CC(OC)=CC=C1CNC(N=C1)=CC=C1CC1=CNC2=NC=CC=C12 NWQSQTFZPMDFOJ-UHFFFAOYSA-N 0.000 description 1
- GMBNOLPTHRSLSY-UHFFFAOYSA-N n-[(4-methylphenyl)methyl]-5-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)pyridin-2-amine Chemical compound C1=CC(C)=CC=C1CNC(N=C1)=CC=C1CC1=CNC2=NC=CC=C12 GMBNOLPTHRSLSY-UHFFFAOYSA-N 0.000 description 1
- BXRLRGFJDCFZKZ-UHFFFAOYSA-N n-[5-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)pyridin-2-yl]-4-(trifluoromethyl)benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C(=O)NC(N=C1)=CC=C1CC1=CNC2=NC=CC=C12 BXRLRGFJDCFZKZ-UHFFFAOYSA-N 0.000 description 1
- JFSMRHZAYXBWDH-UHFFFAOYSA-N n-[5-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)pyridin-2-yl]-4-(trifluoromethyl)benzenesulfonamide Chemical compound C1=CC(C(F)(F)F)=CC=C1S(=O)(=O)NC(N=C1)=CC=C1CC1=CNC2=NC=CC=C12 JFSMRHZAYXBWDH-UHFFFAOYSA-N 0.000 description 1
- AXUXJHPAXYISIR-UHFFFAOYSA-N n-[5-(1h-pyrrolo[2,3-b]pyridine-3-carbonyl)pyridin-2-yl]-4-(trifluoromethyl)benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C(=O)NC1=CC=C(C(=O)C=2C3=CC=CN=C3NC=2)C=N1 AXUXJHPAXYISIR-UHFFFAOYSA-N 0.000 description 1
- RUUFEMAFJKPNAB-UHFFFAOYSA-N n-[5-(1h-pyrrolo[2,3-b]pyridine-3-carbonyl)pyridin-2-yl]-4-(trifluoromethyl)benzenesulfonamide Chemical compound C1=CC(C(F)(F)F)=CC=C1S(=O)(=O)NC1=CC=C(C(=O)C=2C3=CC=CN=C3NC=2)C=N1 RUUFEMAFJKPNAB-UHFFFAOYSA-N 0.000 description 1
- WNYSBUDVPURTSD-UHFFFAOYSA-N n-[[4-chloro-3-(trifluoromethyl)phenyl]methyl]-5-[methoxy(1h-pyrrolo[2,3-b]pyridin-3-yl)methyl]pyridin-2-amine Chemical compound C=1NC2=NC=CC=C2C=1C(OC)C(C=N1)=CC=C1NCC1=CC=C(Cl)C(C(F)(F)F)=C1 WNYSBUDVPURTSD-UHFFFAOYSA-N 0.000 description 1
- FWIOUWIUXVHMKW-UHFFFAOYSA-N n-benzyl-3,5-dimethyl-4-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)pyrazole-1-carboxamide Chemical compound CC1=C(CC=2C3=CC=CN=C3NC=2)C(C)=NN1C(=O)NCC1=CC=CC=C1 FWIOUWIUXVHMKW-UHFFFAOYSA-N 0.000 description 1
- VKMQVCZOMREOER-UHFFFAOYSA-N n-benzyl-5-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)pyridin-2-amine Chemical compound C=1C=C(CC=2C3=CC=CN=C3NC=2)C=NC=1NCC1=CC=CC=C1 VKMQVCZOMREOER-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000007922 nasal spray Substances 0.000 description 1
- 229940097496 nasal spray Drugs 0.000 description 1
- 239000006218 nasal suppository Substances 0.000 description 1
- 239000006199 nebulizer Substances 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
- 230000030991 negative regulation of bone resorption Effects 0.000 description 1
- 230000007302 negative regulation of cytokine production Effects 0.000 description 1
- 230000031987 negative regulation of mast cell apoptotic process Effects 0.000 description 1
- 229960004927 neomycin Drugs 0.000 description 1
- 208000025189 neoplasm of testis Diseases 0.000 description 1
- 230000001613 neoplastic effect Effects 0.000 description 1
- 210000003757 neuroblast Anatomy 0.000 description 1
- 230000002981 neuropathic effect Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 210000000440 neutrophil Anatomy 0.000 description 1
- 230000003448 neutrophilic effect Effects 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002816 nickel compounds Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 230000037311 normal skin Effects 0.000 description 1
- 210000001331 nose Anatomy 0.000 description 1
- 239000002853 nucleic acid probe Substances 0.000 description 1
- 210000004940 nucleus Anatomy 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 210000004789 organ system Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- 230000002177 osteoclastogenic effect Effects 0.000 description 1
- 230000000010 osteolytic effect Effects 0.000 description 1
- 208000002865 osteopetrosis Diseases 0.000 description 1
- 230000002018 overexpression Effects 0.000 description 1
- 229940116315 oxalic acid Drugs 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 238000007833 oxidative deamination reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 235000019371 penicillin G benzathine Nutrition 0.000 description 1
- XYJRXVWERLGGKC-UHFFFAOYSA-D pentacalcium;hydroxide;triphosphate Chemical compound [OH-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O XYJRXVWERLGGKC-UHFFFAOYSA-D 0.000 description 1
- 239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 230000008782 phagocytosis Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229940080469 phosphocellulose Drugs 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 210000002826 placenta Anatomy 0.000 description 1
- 239000013600 plasmid vector Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 230000008488 polyadenylation Effects 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 229940116317 potato starch Drugs 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 229940069328 povidone Drugs 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003141 primary amines Chemical class 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
- 238000012545 processing Methods 0.000 description 1
- 238000004393 prognosis Methods 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 230000000770 proinflammatory effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000001742 protein purification Methods 0.000 description 1
- 230000030788 protein refolding Effects 0.000 description 1
- 230000017854 proteolysis Effects 0.000 description 1
- 208000009305 pseudorabies Diseases 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000004929 pyrrolidonyl group Chemical group N1(C(CCC1)=O)* 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000000163 radioactive labelling Methods 0.000 description 1
- 238000002601 radiography Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010188 recombinant method Methods 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
- HSSLDCABUXLXKM-UHFFFAOYSA-N resorufin Chemical compound C1=CC(=O)C=C2OC3=CC(O)=CC=C3N=C21 HSSLDCABUXLXKM-UHFFFAOYSA-N 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 108091008146 restriction endonucleases Proteins 0.000 description 1
- 210000001995 reticulocyte Anatomy 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229940100486 rice starch Drugs 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 229960002052 salbutamol Drugs 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229960004017 salmeterol Drugs 0.000 description 1
- 238000003345 scintillation counting Methods 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000013545 self-assembled monolayer Substances 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 230000007781 signaling event Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 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
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 238000002415 sodium dodecyl sulfate polyacrylamide gel electrophoresis Methods 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000011697 sodium iodate Substances 0.000 description 1
- 235000015281 sodium iodate Nutrition 0.000 description 1
- 229940032753 sodium iodate Drugs 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000012439 solid excipient Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 230000021595 spermatogenesis Effects 0.000 description 1
- 150000003408 sphingolipids Chemical class 0.000 description 1
- WWUZIQQURGPMPG-KRWOKUGFSA-N sphingosine Chemical compound CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)CO WWUZIQQURGPMPG-KRWOKUGFSA-N 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000005717 substituted cycloalkylene group Chemical group 0.000 description 1
- 238000009495 sugar coating Methods 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003461 sulfonyl halides Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229960002180 tetracycline Drugs 0.000 description 1
- 229930101283 tetracycline Natural products 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 108060008226 thioredoxin Proteins 0.000 description 1
- 229940094937 thioredoxin Drugs 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- LERNTVKEWCAPOY-DZZGSBJMSA-N tiotropium Chemical compound O([C@H]1C[C@@H]2[N+]([C@H](C1)[C@@H]1[C@H]2O1)(C)C)C(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 LERNTVKEWCAPOY-DZZGSBJMSA-N 0.000 description 1
- 229940110309 tiotropium Drugs 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 229960000707 tobramycin Drugs 0.000 description 1
- NLVFBUXFDBBNBW-PBSUHMDJSA-N tobramycin Chemical compound N[C@@H]1C[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N NLVFBUXFDBBNBW-PBSUHMDJSA-N 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- 230000002103 transcriptional effect Effects 0.000 description 1
- 230000037317 transdermal delivery Effects 0.000 description 1
- 238000010361 transduction Methods 0.000 description 1
- 230000026683 transduction Effects 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 102000035160 transmembrane proteins Human genes 0.000 description 1
- 108091005703 transmembrane proteins Proteins 0.000 description 1
- 102000027257 transmembrane receptors Human genes 0.000 description 1
- 108091008578 transmembrane receptors Proteins 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 229960002117 triamcinolone acetonide Drugs 0.000 description 1
- YNDXUCZADRHECN-JNQJZLCISA-N triamcinolone acetonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O YNDXUCZADRHECN-JNQJZLCISA-N 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 150000005671 trienes Chemical class 0.000 description 1
- XQKBFQXWZCFNFF-UHFFFAOYSA-K triiodosamarium Chemical compound I[Sm](I)I XQKBFQXWZCFNFF-UHFFFAOYSA-K 0.000 description 1
- NFHRNKANAAGQOH-UHFFFAOYSA-N triphenylstannane Chemical compound C1=CC=CC=C1[SnH](C=1C=CC=CC=1)C1=CC=CC=C1 NFHRNKANAAGQOH-UHFFFAOYSA-N 0.000 description 1
- 210000002993 trophoblast Anatomy 0.000 description 1
- 230000005748 tumor development Effects 0.000 description 1
- 230000005740 tumor formation Effects 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 230000005751 tumor progression Effects 0.000 description 1
- 210000004026 tunica intima Anatomy 0.000 description 1
- 241001529453 unidentified herpesvirus Species 0.000 description 1
- 241001515965 unidentified phage Species 0.000 description 1
- AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 description 1
- 208000007089 vaccinia Diseases 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 210000005166 vasculature Anatomy 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
- 239000003871 white petrolatum Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 210000005253 yeast cell Anatomy 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- 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
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- 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
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
- A61P3/14—Drugs for disorders of the metabolism for electrolyte homeostasis for calcium homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- 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
- 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
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Physical Education & Sports Medicine (AREA)
- Hematology (AREA)
- Rheumatology (AREA)
- Immunology (AREA)
- Obesity (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pulmonology (AREA)
- Oncology (AREA)
- Endocrinology (AREA)
- Urology & Nephrology (AREA)
- Transplantation (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Ophthalmology & Optometry (AREA)
- Vascular Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Emergency Medicine (AREA)
- Surgery (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US68206305P | 2005-05-17 | 2005-05-17 | |
| US68204205P | 2005-05-17 | 2005-05-17 | |
| US68205105P | 2005-05-17 | 2005-05-17 | |
| US69275005P | 2005-06-22 | 2005-06-22 | |
| US69296005P | 2005-06-22 | 2005-06-22 | |
| PCT/US2006/018726 WO2007013896A2 (en) | 2005-05-17 | 2006-05-16 | Pyrrol (2,3-b) pyridine derivatives protein kinase inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008545652A true JP2008545652A (ja) | 2008-12-18 |
| JP2008545652A5 JP2008545652A5 (enExample) | 2009-07-02 |
Family
ID=37683773
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008512402A Pending JP2008545652A (ja) | 2005-05-17 | 2006-05-16 | ｃ−ｋｉｔおよびｃ−ｆｍｓ活性を調節する化合物およびその用途 |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US7846941B2 (enExample) |
| EP (1) | EP1885723A2 (enExample) |
| JP (1) | JP2008545652A (enExample) |
| KR (1) | KR20080027775A (enExample) |
| AU (1) | AU2006272951A1 (enExample) |
| BR (1) | BRPI0610066A2 (enExample) |
| CA (1) | CA2608733A1 (enExample) |
| CR (1) | CR9591A (enExample) |
| EC (1) | ECSP077985A (enExample) |
| IL (1) | IL187344A0 (enExample) |
| MX (1) | MX2007014377A (enExample) |
| NO (1) | NO20075992L (enExample) |
| NZ (1) | NZ563444A (enExample) |
| WO (1) | WO2007013896A2 (enExample) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012510972A (ja) * | 2008-12-05 | 2012-05-17 | エフ．ホフマン−ラ ロシュ アーゲー | ピロロピラジニル尿素キナーゼ阻害薬 |
| JP2013510166A (ja) * | 2009-11-06 | 2013-03-21 | プレキシコン インコーポレーテッド | キナーゼ調節のための化合物、方法およびその適用 |
| JP2013515070A (ja) * | 2009-12-21 | 2013-05-02 | アレイ バイオファーマ、インコーポレイテッド | ｃＦＭＳ阻害剤としての置換Ｎ−（１Ｈ−インダゾール−４−イル）イミダゾ［１，２−ａ］ピリジン−３−カルボキサミド化合物 |
| JP2013525363A (ja) * | 2010-04-21 | 2013-06-20 | プレキシコン インコーポレーテッド | キナーゼ調節のための化合物および方法、ならびにそれらの適応症 |
| JP2014510131A (ja) * | 2011-04-05 | 2014-04-24 | ファイザー・リミテッド | トロポミオシン関連キナーゼ阻害薬としてのピロロ［２，３−ｄ］ピリミジン誘導体 |
| JP2016509583A (ja) * | 2012-12-21 | 2016-03-31 | プレキシコン インコーポレーテッドＰｌｅｘｘｉｋｏｎ Ｉｎｃ． | キナーゼ調節のための化合物および方法、ならびにその適応 |
| JP2018524381A (ja) * | 2015-07-20 | 2018-08-30 | ジェンザイム・コーポレーション | コロニー刺激因子−１受容体（ｃｓｆ−１ｒ）阻害剤 |
| JP2019531289A (ja) * | 2016-09-16 | 2019-10-31 | ヘルムホルツ ツェントゥルム ミュンヘン ドイチェス フォルシュングスツェントゥルム フューア ゲズントハイト ウント ウムヴェルト （ゲーエムベーハー） | Ｔｒａｆ６阻害剤 |
| JP2020524159A (ja) * | 2017-06-19 | 2020-08-13 | アビスコ セラピューティクス カンパニー リミテッド | Ｃｓｆ−１ｒ阻害活性を有するアザアリール誘導体、その製造方法および応用 |
| US11530216B2 (en) | 2020-12-23 | 2022-12-20 | Genzyme Corporation | Deuterated colony stimulating factor-1 receptor (CSF-1R) inhibitors |
Families Citing this family (92)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SI1696920T1 (sl) | 2003-12-19 | 2015-02-27 | Plexxikon Inc. | Spojine in postopki za razvoj modulatorjev ret |
| US7498342B2 (en) * | 2004-06-17 | 2009-03-03 | Plexxikon, Inc. | Compounds modulating c-kit activity |
| JP4834553B2 (ja) | 2004-09-17 | 2011-12-14 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 医薬組成物 |
| JP2008545652A (ja) * | 2005-05-17 | 2008-12-18 | プレキシコン，インコーポレーテッド | ｃ−ｋｉｔおよびｃ−ｆｍｓ活性を調節する化合物およびその用途 |
| WO2007002325A1 (en) * | 2005-06-22 | 2007-01-04 | Plexxikon, Inc. | Pyrrolo[2,3-b] pyridine derivatives as protein kinase inhibitors |
| JP4989476B2 (ja) | 2005-08-02 | 2012-08-01 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 血管新生阻害物質の効果を検定する方法 |
| AU2006285673B2 (en) * | 2005-09-01 | 2010-12-02 | Eisai R&D Management Co., Ltd. | Method for preparation of pharmaceutical composition having improved disintegratability |
| WO2007084667A2 (en) * | 2006-01-19 | 2007-07-26 | Osi Pharmaceutical, Inc. | Fused heterobicyclic kinase inhibitors |
| EP2865381A1 (en) * | 2006-05-18 | 2015-04-29 | Pharmacyclics, Inc. | ITK inhibitors for treating blood cell malignancies |
| EP2036557B1 (en) | 2006-05-18 | 2015-10-21 | Eisai R&D Management Co., Ltd. | Antitumor agent for thyroid cancer |
| WO2008063888A2 (en) | 2006-11-22 | 2008-05-29 | Plexxikon, Inc. | Compounds modulating c-fms and/or c-kit activity and uses therefor |
| WO2008079909A1 (en) * | 2006-12-21 | 2008-07-03 | Plexxikon, Inc. | Pyrrolo [2,3-b] pyridines as kinase modulators |
| PE20081581A1 (es) * | 2006-12-21 | 2008-11-12 | Plexxikon Inc | COMPUESTOS PIRROLO[2,3-b]PIRIDINAS COMO MODULADORES DE QUINASA |
| AU2007336811A1 (en) * | 2006-12-21 | 2008-07-03 | Plexxikon, Inc. | Compounds and methods for kinase modulation, and indications therefor |
| BRPI0814423B1 (pt) * | 2007-07-17 | 2022-04-19 | Plexxikon, Inc | Compostos que modulam quinase e composição farmacêutica compreendendo os mesmos |
| TW200924762A (en) | 2007-11-02 | 2009-06-16 | Vertex Pharma | Kinase inhibitors |
| ES2400202T3 (es) | 2008-02-29 | 2013-04-08 | Array Biopharma, Inc. | Inhibidores de RAF de pirazol[3,4-B]piridina |
| CA2716951A1 (en) * | 2008-02-29 | 2009-09-11 | Array Biopharma Inc. | Raf inhibitor compounds and methods of use thereof |
| JP2011513332A (ja) | 2008-02-29 | 2011-04-28 | アレイ バイオファーマ、インコーポレイテッド | 癌の治療のためのｒａｆ阻害剤としてのｎ−（６−アミノピリジン−３−イル）−３−（スルホンアミド）ベンズアミド誘導体 |
| WO2009111277A1 (en) * | 2008-02-29 | 2009-09-11 | Array Biopharma Inc. | Imdizo [4. 5-b] pyridine derivatives used as raf inhibitors |
| PE20091846A1 (es) | 2008-05-19 | 2009-12-16 | Plexxikon Inc | DERIVADOS DE PIRROLO[2,3-d]-PIRIMIDINA COMO MODULADORES DE CINASAS |
| WO2009143018A2 (en) | 2008-05-19 | 2009-11-26 | Plexxikon, Inc. | Compounds and methods for kinase modulation, and indications therefor |
| WO2009152087A1 (en) * | 2008-06-10 | 2009-12-17 | Plexxikon, Inc. | Bicyclic heteroaryl compounds and methods for kinase modulation, and indications therefor |
| EP2313411A1 (en) * | 2008-06-10 | 2011-04-27 | Plexxikon, Inc. | 5h-pyrr0l0 [2,3-b]pyrazine derivatives for kinase modulation, and indications therefor |
| EP2356116A1 (en) | 2008-11-20 | 2011-08-17 | OSI Pharmaceuticals, Inc. | Substituted pyrroloý2,3-b¨-pyridines and-pyrazines |
| WO2010111527A1 (en) * | 2009-03-26 | 2010-09-30 | Plexxikon, Inc. | Pyrazolo [ 3, 4 -b] pyridines as kinase inhibitors and their medical use |
| JP5511942B2 (ja) | 2009-04-03 | 2014-06-04 | エフ ホフマン−ラ ロッシュ アクチェン ゲゼルシャフト | 組成物及びその使用 |
| US8329724B2 (en) | 2009-08-03 | 2012-12-11 | Hoffmann-La Roche Inc. | Process for the manufacture of pharmaceutically active compounds |
| US8648086B2 (en) | 2009-08-24 | 2014-02-11 | Ascepion Pharmaceuticals, Inc. | 5,6-bicyclic heteroaryl-containing urea compounds as kinase inhibitors |
| CN102712635A (zh) | 2009-08-28 | 2012-10-03 | 阵列生物制药公司 | 用于抑制raf激酶的1h-吡唑并[3,4-b]吡啶化合物 |
| MX2012005827A (es) | 2009-11-18 | 2012-06-19 | Plexxikon Inc | Compuestos y metodos para la modulacion de cinasas, e indicaciones para ello. |
| JP5815558B2 (ja) | 2009-12-23 | 2015-11-17 | プレキシコン インコーポレーテッドＰｌｅｘｘｉｋｏｎ Ｉｎｃ． | キナーゼ調節のための化合物及び方法ならびにそれらの適応症 |
| KR20120124428A (ko) | 2009-12-30 | 2012-11-13 | 아르퀼 인코포레이티드 | 치환된 피롤로-아미노피리미딘 화합물 |
| JP2013526570A (ja) | 2010-05-14 | 2013-06-24 | オーエスアイ・ファーマシューティカルズ，エルエルシー | 縮合二環式キナーゼ阻害剤 |
| AR081039A1 (es) | 2010-05-14 | 2012-05-30 | Osi Pharmaceuticals Llc | Inhibidores biciclicos fusionados de quinasa |
| SI2672967T1 (sl) | 2011-02-07 | 2018-12-31 | Plexxikon Inc. | Spojine in postopki za kinazno modulacijo in indikacije zanjo |
| TWI558702B (zh) | 2011-02-21 | 2016-11-21 | 普雷辛肯公司 | 醫藥活性物質的固態形式 |
| US8962650B2 (en) | 2011-04-18 | 2015-02-24 | Eisai R&D Management Co., Ltd. | Therapeutic agent for tumor |
| EP2710003A1 (en) | 2011-05-16 | 2014-03-26 | OSI Pharmaceuticals, LLC | Fused bicyclic kinase inhibitors |
| CA2836474A1 (en) | 2011-05-17 | 2012-11-22 | Plexxikon Inc. | Kinase modulation and indications therefor |
| JP6038128B2 (ja) | 2011-06-03 | 2016-12-07 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | レンバチニブ化合物に対する甲状腺癌対象及び腎臓癌対象の反応性を予測及び評価するためのバイオマーカー |
| EP2797888B1 (en) | 2011-12-31 | 2016-06-08 | BeiGene, Ltd. | Fused tricyclic compounds as raf kinase inhibitors |
| US9358235B2 (en) | 2012-03-19 | 2016-06-07 | Plexxikon Inc. | Kinase modulation, and indications therefor |
| US9150570B2 (en) | 2012-05-31 | 2015-10-06 | Plexxikon Inc. | Synthesis of heterocyclic compounds |
| CN104704129A (zh) | 2012-07-24 | 2015-06-10 | 药品循环公司 | 与对布鲁顿酪氨酸激酶(btk)抑制剂的抗性相关的突变 |
| JP6318156B2 (ja) | 2012-09-06 | 2018-04-25 | プレキシコン インコーポレーテッドＰｌｅｘｘｉｋｏｎ Ｉｎｃ． | キナーゼをモジュレートするための化合物および方法、ならびにその指標 |
| WO2014053968A1 (en) | 2012-10-04 | 2014-04-10 | Pfizer Limited | Pyrrolo[3,2-c]pyridine tropomyosin-related kinase inhibitors |
| US9334239B2 (en) | 2012-12-21 | 2016-05-10 | Eisai R&D Management Co., Ltd. | Amorphous form of quinoline derivative, and method for producing same |
| US20140303121A1 (en) | 2013-03-15 | 2014-10-09 | Plexxikon Inc. | Heterocyclic compounds and uses thereof |
| CA2903293C (en) | 2013-03-15 | 2020-10-13 | Plexxikon Inc. | Heterocyclic compounds and uses thereof |
| MX368099B (es) | 2013-05-14 | 2019-09-19 | Eisai R&D Man Co Ltd | Biomarcadores para predecir y evaluar el grado de respuesta de sujetos con cancer de endometrio a compuestos de tipo lenvatinib. |
| WO2014194127A1 (en) | 2013-05-30 | 2014-12-04 | Plexxikon Inc. | Compounds for kinase modulation, and indications therefor |
| WO2014206344A1 (en) | 2013-06-28 | 2014-12-31 | Beigene, Ltd. | Fused tricyclic amide compounds as multiple kinase inhibitors |
| WO2015134536A1 (en) | 2014-03-04 | 2015-09-11 | Plexxikon Inc. | Compounds and methods for kinase modulation, and indications therefor |
| US9580416B2 (en) | 2014-07-02 | 2017-02-28 | Pharmacyclics Llc | Inhibitors of Bruton's tyrosine kinase |
| JP6659554B2 (ja) | 2014-08-28 | 2020-03-04 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 高純度キノリン誘導体およびその製造方法 |
| ES2774177T3 (es) | 2014-09-15 | 2020-07-17 | Plexxikon Inc | Compuestos heterocíclicos y usos de estos |
| HUE064614T2 (hu) | 2015-02-25 | 2024-04-28 | Eisai R&D Man Co Ltd | Eljárás egy kinolin-származék keserû ízének elnyomására |
| KR20240064733A (ko) | 2015-03-04 | 2024-05-13 | 머크 샤프 앤드 돔 코포레이션 | 암을 치료하기 위한 pd-1 길항제 및 vegfr/fgfr/ret 티로신 키나제 억제제의 조합 |
| US10160755B2 (en) | 2015-04-08 | 2018-12-25 | Plexxikon Inc. | Compounds and methods for kinase modulation, and indications therefor |
| LT3292123T (lt) | 2015-05-06 | 2020-12-28 | Plexxikon Inc. | Junginio, moduliuojančio kinazes, kietos formos |
| CN112574196A (zh) | 2015-05-06 | 2021-03-30 | 普莱希科公司 | 调节激酶的1H-吡咯并[2,3-b]吡啶衍生物的合成 |
| BR112017027227B1 (pt) | 2015-06-16 | 2023-12-12 | Eisai R&D Management Co., Ltd | Agente anti-câncer |
| US10829484B2 (en) | 2015-07-28 | 2020-11-10 | Plexxikon Inc. | Compounds and methods for kinase modulation, and indications therefor |
| JP6553726B2 (ja) | 2015-08-20 | 2019-07-31 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 腫瘍治療剤 |
| AU2016328619B2 (en) | 2015-09-21 | 2020-07-16 | Opna Bio SA | Heterocyclic compounds and uses thereof |
| MX2018006856A (es) | 2015-12-07 | 2018-08-01 | Plexxikon Inc | Compuestos y metodos para modulacion de la quinasa, e indicaciones de los mismos. |
| US9630968B1 (en) | 2015-12-23 | 2017-04-25 | Arqule, Inc. | Tetrahydropyranyl amino-pyrrolopyrimidinone and methods of use thereof |
| ES2904615T3 (es) | 2016-03-16 | 2022-04-05 | Plexxikon Inc | Compuestos y métodos para la modulación de quinasas e indicaciones al respecto |
| RU2019108280A (ru) | 2016-08-24 | 2020-09-25 | Аркьюл, Инк. | Аминопирролопиримидиноновые соединения и способы их применения |
| TW201815766A (zh) | 2016-09-22 | 2018-05-01 | 美商普雷辛肯公司 | 用於ｉｄｏ及ｔｄｏ調節之化合物及方法以及其適應症 |
| WO2018136202A2 (en) | 2016-12-23 | 2018-07-26 | Plexxikon Inc. | Compounds and methods for cdk8 modulation and indications therefor |
| KR102539920B1 (ko) | 2017-02-08 | 2023-06-05 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 종양-치료용 약제학적 조성물 |
| US10577366B2 (en) | 2017-03-20 | 2020-03-03 | Plexxikon Inc. | Crystalline forms of a compound that inhibits bromodomain |
| US20200197384A1 (en) | 2017-05-16 | 2020-06-25 | Eisai R&D Management Co., Ltd. | Treatment of hepatocellular carcinoma |
| WO2018226846A1 (en) | 2017-06-07 | 2018-12-13 | Plexxikon Inc. | Compounds and methods for kinase modulation |
| AU2018307910B2 (en) | 2017-07-25 | 2024-07-25 | Daiichi Sankyo Company, Limited | Formulations of a compound modulating kinases |
| US10717735B2 (en) | 2017-10-13 | 2020-07-21 | Plexxikon Inc. | Solid forms of a compound for modulating kinases |
| EP3700574B1 (en) | 2017-10-27 | 2024-08-28 | Plexxikon Inc. | Formulations of a compound modulating kinases |
| DK3746437T3 (da) | 2018-01-31 | 2024-11-11 | Heparegenix Gmbh | MKK4-proteinkinaseinhibitorer til at fremme leverregenerering eller reducere eller forebygge hepatocytdød |
| AU2019239952A1 (en) | 2018-03-20 | 2020-10-08 | Plexxikon Inc. | Compounds and methods for IDO and TDO modulation, and indications therefor |
| EP3810139A1 (en) | 2018-06-21 | 2021-04-28 | HepaRegeniX GmbH | Tricyclic protein kinase inhibitors for promoting liver regeneration or reducing or preventing hepatocyte death |
| IL279641B2 (en) | 2018-07-16 | 2024-04-01 | Heparegenix Gmbh | Protein kinase inhibitors for promoting liver regeneration or reducing or preventing hepatocyte death |
| CN112867803A (zh) | 2018-10-16 | 2021-05-28 | 诺华股份有限公司 | 单独的或与免疫标志物组合的肿瘤突变负荷作为生物标志物用于预测对靶向疗法的应答 |
| EP3953351A1 (en) | 2019-04-09 | 2022-02-16 | Plexxikon Inc. | Condensed azines for ep300 or cbp modulation and indications therefor |
| US12466826B2 (en) | 2020-01-15 | 2025-11-11 | Heparegenix Gmbh | 3-benzoyl-1H-pyrrolo[2,3-b]pyridine derivatives as MKK4 inhibitors for treating liver diseases |
| WO2021144360A1 (en) | 2020-01-17 | 2021-07-22 | F. Hoffmann-La Roche Ag | Small molecule csf-1r inhibitors in therapeutic and cosmetic uses |
| WO2021216898A1 (en) | 2020-04-23 | 2021-10-28 | Plexxikon Inc. | Compounds and methods for cd73 modulation and indications therefor |
| KR20230028254A (ko) | 2020-04-29 | 2023-02-28 | 플렉시콘 인코퍼레이티드 | 헤테로사이클릭 화합물의 합성 |
| JP2023542473A (ja) | 2020-08-21 | 2023-10-10 | プレキシコン インコーポレーテッド | 併用薬抗がん治療 |
| CN117321418A (zh) | 2021-03-18 | 2023-12-29 | 诺华股份有限公司 | 癌症生物标志物及其使用方法 |
| CN115557985B (zh) * | 2022-12-06 | 2023-03-10 | 成都泰蓉生物科技有限公司 | 一种选择性裂解硫醚中c-s键合成硅烷的方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007521334A (ja) * | 2003-12-19 | 2007-08-02 | プレキシコン，インコーポレーテッド | Ｒｅｔ調節剤の開発のための化合物および方法 |
| JP2008500330A (ja) * | 2004-05-27 | 2008-01-10 | ファイザー・プロダクツ・インク | 癌治療に有用なピロロピリミジン誘導体 |
| JP2008503473A (ja) * | 2004-06-17 | 2008-02-07 | プレキシコン，インコーポレーテッド | Ｃ−ｋｉｔ活性を調節する化合物 |
Family Cites Families (131)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US617687A (en) * | 1899-01-10 | Vapor-burning apparatus | ||
| US2234705A (en) * | 1940-04-12 | 1941-03-11 | Eastman Kodak Co | Cellulose organic derivative composition containing esters of monoalkoxy benzoic acids |
| US2413258A (en) * | 1942-07-07 | 1946-12-24 | United Gas Improvement Co | Polystyrene-type resins plasticized with high boiling fatty acid alkyl esters |
| DE2413258A1 (de) | 1974-03-20 | 1975-10-02 | Bayer Ag | Alkoxycarbonylphenylharnstoffe, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| GB1573212A (en) * | 1976-04-15 | 1980-08-20 | Technicon Instr | Immunoassay for gentamicin |
| US4664504A (en) * | 1983-01-20 | 1987-05-12 | Tokyo Shibaura Denki Kabushiki Kaisha | Image forming apparatus |
| US4568649A (en) * | 1983-02-22 | 1986-02-04 | Immunex Corporation | Immediate ligand detection assay |
| US4626513A (en) * | 1983-11-10 | 1986-12-02 | Massachusetts General Hospital | Method and apparatus for ligand detection |
| EP0154734B1 (en) | 1984-03-15 | 1990-08-29 | Immunex Corporation | Immediate ligand detection assay, a test kit and its formation |
| US5688655A (en) * | 1988-02-10 | 1997-11-18 | Ict Pharmaceuticals, Inc. | Method of screening for protein inhibitors and activators |
| US6054270A (en) | 1988-05-03 | 2000-04-25 | Oxford Gene Technology Limited | Analying polynucleotide sequences |
| US5700637A (en) | 1988-05-03 | 1997-12-23 | Isis Innovation Limited | Apparatus and method for analyzing polynucleotide sequences and method of generating oligonucleotide arrays |
| US5658775A (en) * | 1988-05-17 | 1997-08-19 | Sloan-Kettering Institute For Cancer Research | Double copy retroviral vector |
| JP3082204B2 (ja) * | 1988-09-01 | 2000-08-28 | ホワイトヘッド・インスティチュート・フォー・バイオメディカル・リサーチ | 両栄養性および環境栄養性宿主域を持つ組換え体レトロウイルス |
| US5703055A (en) | 1989-03-21 | 1997-12-30 | Wisconsin Alumni Research Foundation | Generation of antibodies through lipid mediated DNA delivery |
| US5143854A (en) * | 1989-06-07 | 1992-09-01 | Affymax Technologies N.V. | Large scale photolithographic solid phase synthesis of polypeptides and receptor binding screening thereof |
| US5744101A (en) | 1989-06-07 | 1998-04-28 | Affymax Technologies N.V. | Photolabile nucleoside protecting groups |
| US5527681A (en) | 1989-06-07 | 1996-06-18 | Affymax Technologies N.V. | Immobilized molecular synthesis of systematically substituted compounds |
| US5800992A (en) | 1989-06-07 | 1998-09-01 | Fodor; Stephen P.A. | Method of detecting nucleic acids |
| WO1991018088A1 (en) | 1990-05-23 | 1991-11-28 | The United States Of America, Represented By The Secretary, United States Department Of Commerce | Adeno-associated virus (aav)-based eucaryotic vectors |
| DE4022414A1 (de) * | 1990-07-13 | 1992-01-16 | Bayer Ag | Substituierte pyrrolo-pyridine |
| EP0659209A1 (en) * | 1991-07-26 | 1995-06-28 | The University Of Rochester | Cancer therapy utilizing malignant cells |
| US5632957A (en) * | 1993-11-01 | 1997-05-27 | Nanogen | Molecular biological diagnostic systems including electrodes |
| FR2687402B1 (fr) * | 1992-02-14 | 1995-06-30 | Lipha | Nouveaux azaindoles, procedes de preparation et medicaments les contenant. |
| JPH05236997A (ja) * | 1992-02-28 | 1993-09-17 | Hitachi Ltd | ポリヌクレオチド捕捉用チップ |
| GB9226855D0 (en) * | 1992-12-23 | 1993-02-17 | Erba Carlo Spa | Vinylene-azaindole derivatives and process for their preparation |
| CN1118598A (zh) * | 1993-03-01 | 1996-03-13 | 默克·夏普-道姆公司 | 吡咯并吡啶衍生物 |
| US5576319A (en) * | 1993-03-01 | 1996-11-19 | Merck, Sharp & Dohme Ltd. | Pyrrolo-pyridine derivatives |
| ATE184008T1 (de) * | 1993-03-01 | 1999-09-15 | Merck Sharp & Dohme | Pyrrolopyridinderivate als dopaminrezeptor liganden |
| US5840485A (en) * | 1993-05-27 | 1998-11-24 | Selectide Corporation | Topologically segregated, encoded solid phase libraries |
| NZ267843A (en) * | 1993-05-27 | 1997-10-24 | Selectide Corp | Libraries of synthetic test compound attached to separate phase synthesis supports |
| US5631236A (en) | 1993-08-26 | 1997-05-20 | Baylor College Of Medicine | Gene therapy for solid tumors, using a DNA sequence encoding HSV-Tk or VZV-Tk |
| US5426039A (en) | 1993-09-08 | 1995-06-20 | Bio-Rad Laboratories, Inc. | Direct molecular cloning of primer extended DNA containing an alkane diol |
| US6045996A (en) * | 1993-10-26 | 2000-04-04 | Affymetrix, Inc. | Hybridization assays on oligonucleotide arrays |
| US6468742B2 (en) * | 1993-11-01 | 2002-10-22 | Nanogen, Inc. | Methods for determination of single nucleic acid polymorphisms using bioelectronic microchip |
| US5965452A (en) * | 1996-07-09 | 1999-10-12 | Nanogen, Inc. | Multiplexed active biologic array |
| US5807522A (en) | 1994-06-17 | 1998-09-15 | The Board Of Trustees Of The Leland Stanford Junior University | Methods for fabricating microarrays of biological samples |
| US5763198A (en) * | 1994-07-22 | 1998-06-09 | Sugen, Inc. | Screening assays for compounds |
| GB9416162D0 (en) | 1994-08-10 | 1994-09-28 | Merck Sharp & Dohme | Therapeutic agents |
| GB9416189D0 (en) | 1994-08-10 | 1994-09-28 | Merck Sharp & Dohme | Therapeutic agents |
| US5556752A (en) * | 1994-10-24 | 1996-09-17 | Affymetrix, Inc. | Surface-bound, unimolecular, double-stranded DNA |
| US5830645A (en) | 1994-12-09 | 1998-11-03 | The Regents Of The University Of California | Comparative fluorescence hybridization to nucleic acid arrays |
| US5837815A (en) | 1994-12-15 | 1998-11-17 | Sugen, Inc. | PYK2 related polypeptide products |
| GB2298199A (en) * | 1995-02-21 | 1996-08-28 | Merck Sharp & Dohme | Synthesis of azaindoles |
| GB9503400D0 (en) | 1995-02-21 | 1995-04-12 | Merck Sharp & Dohme | Therpeutic agents |
| US5959098A (en) | 1996-04-17 | 1999-09-28 | Affymetrix, Inc. | Substrate preparation process |
| US6117681A (en) | 1995-03-29 | 2000-09-12 | Bavarian Nordic Research Inst. A/S | Pseudotyped retroviral particles |
| GB9507291D0 (en) * | 1995-04-07 | 1995-05-31 | Merck Sharp & Dohme | Therapeutic agents |
| GB2299581A (en) | 1995-04-07 | 1996-10-09 | Merck Sharp & Dohme | 3-(Tetrahydropyridin-1-yl-methyl)pyrrolo[2,3-b]pyridine derivatives as ligands for dopamine receptor subtypes |
| US6110456A (en) * | 1995-06-07 | 2000-08-29 | Yale University | Oral delivery or adeno-associated viral vectors |
| US5856174A (en) * | 1995-06-29 | 1999-01-05 | Affymetrix, Inc. | Integrated nucleic acid diagnostic device |
| US5866411A (en) | 1995-09-08 | 1999-02-02 | Pedersen; Finn Skou | Retroviral vector, a replication system for said vector and avian or mammalian cells transfected with said vector |
| US5747276A (en) * | 1995-09-15 | 1998-05-05 | The Scripps Research Institute | Screening methods for the identification of novel antibiotics |
| US5721118A (en) | 1995-10-31 | 1998-02-24 | The Regents Of The University Of California, San Diego | Mammalian artificial chromosomes and methods of using same |
| US6022963A (en) * | 1995-12-15 | 2000-02-08 | Affymetrix, Inc. | Synthesis of oligonucleotide arrays using photocleavable protecting groups |
| US6013440A (en) * | 1996-03-11 | 2000-01-11 | Affymetrix, Inc. | Nucleic acid affinity columns |
| US6025155A (en) * | 1996-04-10 | 2000-02-15 | Chromos Molecular Systems, Inc. | Artificial chromosomes, uses thereof and methods for preparing artificial chromosomes |
| US5804585A (en) * | 1996-04-15 | 1998-09-08 | Texas Biotechnology Corporation | Thieno-pyridine sulfonamides derivatives thereof and related compounds that modulate the activity of endothelin |
| WO1997046313A1 (en) | 1996-06-07 | 1997-12-11 | Eos Biotechnology, Inc. | Immobilised linear oligonucleotide arrays |
| US6294330B1 (en) * | 1997-01-31 | 2001-09-25 | Odyssey Pharmaceuticals Inc. | Protein fragment complementation assays for the detection of biological or drug interactions |
| AU6443498A (en) * | 1997-03-07 | 1998-09-22 | Tropix, Inc. | Protease inhibtor assay |
| US6096718A (en) | 1997-06-05 | 2000-08-01 | Gene Targeting Corp. | Tissue specific adenovirus vectors for breast cancer treatment |
| US6235769B1 (en) * | 1997-07-03 | 2001-05-22 | Sugen, Inc. | Methods of preventing and treating neurological disorders with compounds that modulate the function of the C-RET receptor protein tyrosine kinase |
| US6826296B2 (en) | 1997-07-25 | 2004-11-30 | Affymetrix, Inc. | Method and system for providing a probe array chip design database |
| US6161776A (en) * | 1997-08-12 | 2000-12-19 | Nibco Inc. | Multi-layered, porous mat turf irrigation apparatus and method |
| CA2300940A1 (en) | 1997-08-15 | 1999-02-25 | Hyseq, Inc. | Methods and compositions for detection or quantification of nucleic acid species |
| ATE272833T1 (de) | 1997-09-11 | 2004-08-15 | Bioventures Inc | Verfahren zur erstellung von arrays hoher dichte |
| US6178384B1 (en) * | 1997-09-29 | 2001-01-23 | The Trustees Of Columbia University In The City Of New York | Method and apparatus for selecting a molecule based on conformational free energy |
| US6465178B2 (en) | 1997-09-30 | 2002-10-15 | Surmodics, Inc. | Target molecule attachment to surfaces |
| CA2323638A1 (en) | 1998-04-03 | 1999-10-14 | Phylos, Inc. | Addressable protein arrays |
| US6048695A (en) * | 1998-05-04 | 2000-04-11 | Baylor College Of Medicine | Chemically modified nucleic acids and methods for coupling nucleic acids to solid support |
| AU4543899A (en) * | 1998-06-08 | 1999-12-30 | Advanced Medicine, Inc. | Multibinding inhibitors of microsomal triglyceride transferase protein |
| US6113913A (en) | 1998-06-26 | 2000-09-05 | Genvec, Inc. | Recombinant adenovirus |
| US6277628B1 (en) | 1998-10-02 | 2001-08-21 | Incyte Genomics, Inc. | Linear microarrays |
| US6277489B1 (en) * | 1998-12-04 | 2001-08-21 | The Regents Of The University Of California | Support for high performance affinity chromatography and other uses |
| US6221653B1 (en) * | 1999-04-27 | 2001-04-24 | Agilent Technologies, Inc. | Method of performing array-based hybridization assays using thermal inkjet deposition of sample fluids |
| FR2793793B1 (fr) * | 1999-05-19 | 2004-02-27 | Adir | Nouveaux derives dimeriques substitues, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| US6653151B2 (en) * | 1999-07-30 | 2003-11-25 | Large Scale Proteomics Corporation | Dry deposition of materials for microarrays using matrix displacement |
| EP1106603A3 (en) | 1999-12-06 | 2003-11-19 | Fuji Photo Film Co., Ltd. | DNA chip and reactive solid carrier |
| CA2395461C (en) | 1999-12-22 | 2010-05-25 | Sugen, Inc. | Methods of modulating c-kit tyrosine kinase function with indolinone compounds |
| CA2707827A1 (en) | 2001-04-11 | 2002-10-24 | Senju Pharmaceutical Co., Ltd. | Visual function disorder improving agents containing rho kinase inhibitors |
| WO2002085896A1 (en) | 2001-04-24 | 2002-10-31 | Wyeth | Antidepressant azaheterocyclylmethyl derivatives of 2,3-dihydro-1,4-benzodioxan |
| GB0114417D0 (en) * | 2001-06-13 | 2001-08-08 | Boc Group Plc | Lubricating systems for regenerative vacuum pumps |
| EP1267111A1 (en) | 2001-06-15 | 2002-12-18 | Dsm N.V. | Pressurized fluid conduit |
| WO2002102783A1 (en) | 2001-06-19 | 2002-12-27 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
| US7291639B2 (en) | 2001-06-20 | 2007-11-06 | Wyeth | Aryloxy-acetic acid compounds useful as inhibitors of plasminogen activator inhibitor-1 (PAI-1) |
| UA75425C2 (en) | 2001-07-09 | 2006-04-17 | Piperazine oxime derivatives with antagonistic activity to nk-1 receptor, use thereof, a pharmaceutical composition based thereon, a method for producing and a method for producing intermediary compounds | |
| GB0117583D0 (en) | 2001-07-19 | 2001-09-12 | Astrazeneca Ab | Novel compounds |
| US6858860B2 (en) * | 2001-07-24 | 2005-02-22 | Seiko Epson Corporation | Apparatus and method for measuring natural period of liquid |
| GB0118479D0 (en) | 2001-07-28 | 2001-09-19 | Astrazeneca Ab | Novel compounds |
| WO2003028724A1 (en) | 2001-10-04 | 2003-04-10 | Smithkline Beecham Corporation | Chk1 kinase inhibitors |
| US20050014942A1 (en) | 2001-10-30 | 2005-01-20 | Yasufumi Maruyama | Amide derivatives and drugs |
| US20030236277A1 (en) | 2002-02-14 | 2003-12-25 | Kadow John F. | Indole, azaindole and related heterocyclic pyrrolidine derivatives |
| US6884889B2 (en) | 2002-03-25 | 2005-04-26 | Bristol-Myers Squibb Co. | Processes for the preparation of antiviral 7-azaindole derivatives |
| AU2003214412A1 (en) | 2002-03-28 | 2003-10-13 | Eisai R & D Management Co., Ltd. | 7-azaindoles as inhibitors of c-jun n-terminal kinases for the treatment of neurodegenerative disorders |
| WO2003082869A1 (en) | 2002-03-28 | 2003-10-09 | Eisai Co., Ltd. | Azaindoles as inhibitors of c-jun n-terminal kinases |
| UA78999C2 (en) | 2002-06-04 | 2007-05-10 | Wyeth Corp | 1-(aminoalkyl)-3-sulfonylazaindoles as ligands of 5-hydroxytryptamine-6 |
| TW200403243A (en) | 2002-07-18 | 2004-03-01 | Wyeth Corp | 1-Heterocyclylalkyl-3-sulfonylazaindole or-azaindazole derivatives as 5-hydroxytryptamine-6 ligands |
| TWI329112B (en) | 2002-07-19 | 2010-08-21 | Bristol Myers Squibb Co | Novel inhibitors of kinases |
| US6878887B2 (en) * | 2002-08-07 | 2005-04-12 | Matsushita Electric Industrial Co., Ltd. | Anti-malfunction mechanism for variable output device |
| SE0202463D0 (sv) | 2002-08-14 | 2002-08-14 | Astrazeneca Ab | Novel compounds |
| AU2003278764C1 (en) | 2002-09-06 | 2010-09-16 | Cerulean Pharma Inc. | Cyclodextrin-based polymers for therapeutic delivery |
| CA2503905A1 (en) * | 2002-09-16 | 2004-03-25 | Plexxikon, Inc. | Crystal structure of pim-1 kinase |
| US7696225B2 (en) * | 2003-01-06 | 2010-04-13 | Osi Pharmaceuticals, Inc. | (2-carboxamido)(3-Amino) thiophene compounds |
| SE0300119D0 (sv) | 2003-01-17 | 2003-01-17 | Astrazeneca Ab | Novel compounds |
| SE0300120D0 (sv) | 2003-01-17 | 2003-01-17 | Astrazeneca Ab | Novel compounds |
| US20050085463A1 (en) * | 2003-01-23 | 2005-04-21 | Weiner David M. | Use of N-desmethylclozapine to treat human neuropsychiatric disease |
| JP2006517966A (ja) | 2003-02-14 | 2006-08-03 | ワイス | ５−ヒドロキシトリプタミン−６リガンドとしてのヘテロサイクリル−３−スルホニルアザインドールまたは−アザインダゾール誘導体 |
| EP1627045A2 (en) * | 2003-02-28 | 2006-02-22 | Plexxikon, Inc. | Pyk2 crystal structure and uses |
| US20050164300A1 (en) * | 2003-09-15 | 2005-07-28 | Plexxikon, Inc. | Molecular scaffolds for kinase ligand development |
| DE10357510A1 (de) | 2003-12-09 | 2005-07-07 | Bayer Healthcare Ag | Heteroarylsubstituierte Benzole |
| GB0330043D0 (en) * | 2003-12-24 | 2004-01-28 | Pharmacia Italia Spa | Pyrrolo [2,3-b] pyridine derivatives active as kinase inhibitors process for their preparation and pharmaceutical compositions comprising them |
| GB0330042D0 (en) | 2003-12-24 | 2004-01-28 | Pharmacia Italia Spa | Pyrrolo [2,3-b] pyridine derivatives active as kinase inhibitors process for their preparation and pharmaceutical compositions them |
| GB0403635D0 (en) | 2004-02-18 | 2004-03-24 | Devgen Nv | Pyridinocarboxamides with improved activity as kinase inhibitors |
| GB0405055D0 (en) | 2004-03-05 | 2004-04-07 | Eisai London Res Lab Ltd | JNK inhibitors |
| BRPI0509369B1 (pt) | 2004-03-30 | 2021-08-03 | Vertex Pharmaceuticals Incorporated | Compostos azaindóis úteis como inibidores de jak e outras proteína cinases e composição farmacêutica |
| US7498342B2 (en) * | 2004-06-17 | 2009-03-03 | Plexxikon, Inc. | Compounds modulating c-kit activity |
| WO2006004984A1 (en) | 2004-06-30 | 2006-01-12 | Vertex Pharmaceuticals Incorporated | Azaindoles useful as inhibitors of protein kinases |
| JP2008508303A (ja) | 2004-07-27 | 2008-03-21 | エスジーエックス ファーマシューティカルズ、インコーポレイテッド | ピロロ−ピリジンキナーゼモジュレーター |
| US7626021B2 (en) * | 2004-07-27 | 2009-12-01 | Sgx Pharmaceuticals, Inc. | Fused ring heterocycle kinase modulators |
| US7361764B2 (en) * | 2004-07-27 | 2008-04-22 | Sgx Pharmaceuticals, Inc. | Pyrrolo-pyridine kinase modulators |
| US7709645B2 (en) * | 2004-07-27 | 2010-05-04 | Sgx Pharmaceuticals, Inc. | Pyrrolo-pyridine kinase modulators |
| BRPI0513899A (pt) * | 2004-07-27 | 2008-05-20 | Sgx Pharmaceuticals Inc | moduladores de cinase heterocìclica de anel fundido |
| AU2006239632B2 (en) | 2005-04-25 | 2012-03-15 | Merck Patent Gmbh | Novel AZA- heterocycles serving as kinase inhibitors |
| JP2008545652A (ja) | 2005-05-17 | 2008-12-18 | プレキシコン，インコーポレーテッド | ｃ−ｋｉｔおよびｃ−ｆｍｓ活性を調節する化合物およびその用途 |
| ZA200710379B (en) | 2005-05-20 | 2009-05-27 | Vertex Pharma | Pyrrolopyridines useful as inhibitors of protein kinase |
| WO2007002325A1 (en) | 2005-06-22 | 2007-01-04 | Plexxikon, Inc. | Pyrrolo[2,3-b] pyridine derivatives as protein kinase inhibitors |
| GB0516156D0 (en) | 2005-08-05 | 2005-09-14 | Eisai London Res Lab Ltd | JNK inhibitors |
| PE20081581A1 (es) * | 2006-12-21 | 2008-11-12 | Plexxikon Inc | COMPUESTOS PIRROLO[2,3-b]PIRIDINAS COMO MODULADORES DE QUINASA |
| WO2008079909A1 (en) * | 2006-12-21 | 2008-07-03 | Plexxikon, Inc. | Pyrrolo [2,3-b] pyridines as kinase modulators |
| CL2008001540A1 (es) * | 2007-05-29 | 2009-05-22 | Sgx Pharmaceuticals Inc | Compuestos derivados de pirrolopiridinas y pirazolopiridinas; composicion farmaceutica; y uso en el tratamiento del cancer. |
-
2006
- 2006-05-16 JP JP2008512402A patent/JP2008545652A/ja active Pending
- 2006-05-16 CA CA002608733A patent/CA2608733A1/en not_active Abandoned
- 2006-05-16 NZ NZ563444A patent/NZ563444A/en not_active IP Right Cessation
- 2006-05-16 EP EP06813186A patent/EP1885723A2/en not_active Withdrawn
- 2006-05-16 KR KR1020077029428A patent/KR20080027775A/ko not_active Withdrawn
- 2006-05-16 MX MX2007014377A patent/MX2007014377A/es active IP Right Grant
- 2006-05-16 BR BRPI0610066-0A patent/BRPI0610066A2/pt not_active IP Right Cessation
- 2006-05-16 WO PCT/US2006/018726 patent/WO2007013896A2/en not_active Ceased
- 2006-05-16 AU AU2006272951A patent/AU2006272951A1/en not_active Abandoned
- 2006-05-16 US US11/435,381 patent/US7846941B2/en active Active
-
2007
- 2007-11-13 IL IL187344A patent/IL187344A0/en unknown
- 2007-11-23 NO NO20075992A patent/NO20075992L/no not_active Application Discontinuation
- 2007-12-07 EC EC2007007985A patent/ECSP077985A/es unknown
- 2007-12-14 CR CR9591A patent/CR9591A/es not_active Application Discontinuation
-
2010
- 2010-12-01 US US12/958,376 patent/US20110166174A1/en not_active Abandoned
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007521334A (ja) * | 2003-12-19 | 2007-08-02 | プレキシコン，インコーポレーテッド | Ｒｅｔ調節剤の開発のための化合物および方法 |
| JP2008500330A (ja) * | 2004-05-27 | 2008-01-10 | ファイザー・プロダクツ・インク | 癌治療に有用なピロロピリミジン誘導体 |
| JP2008503473A (ja) * | 2004-06-17 | 2008-02-07 | プレキシコン，インコーポレーテッド | Ｃ−ｋｉｔ活性を調節する化合物 |
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012510972A (ja) * | 2008-12-05 | 2012-05-17 | エフ．ホフマン−ラ ロシュ アーゲー | ピロロピラジニル尿素キナーゼ阻害薬 |
| JP2016106090A (ja) * | 2009-11-06 | 2016-06-16 | プレキシコン インコーポレーテッドＰｌｅｘｘｉｋｏｎ Ｉｎｃ． | キナーゼ調節のための化合物、方法およびその適用 |
| JP2013510166A (ja) * | 2009-11-06 | 2013-03-21 | プレキシコン インコーポレーテッド | キナーゼ調節のための化合物、方法およびその適用 |
| JP2013515070A (ja) * | 2009-12-21 | 2013-05-02 | アレイ バイオファーマ、インコーポレイテッド | ｃＦＭＳ阻害剤としての置換Ｎ−（１Ｈ−インダゾール−４−イル）イミダゾ［１，２−ａ］ピリジン−３−カルボキサミド化合物 |
| JP2013525363A (ja) * | 2010-04-21 | 2013-06-20 | プレキシコン インコーポレーテッド | キナーゼ調節のための化合物および方法、ならびにそれらの適応症 |
| JP2016028073A (ja) * | 2010-04-21 | 2016-02-25 | プレキシコン インコーポレーテッドＰｌｅｘｘｉｋｏｎ Ｉｎｃ． | キナーゼ調節のための化合物および方法、ならびにそれらの適応症 |
| JP2014510131A (ja) * | 2011-04-05 | 2014-04-24 | ファイザー・リミテッド | トロポミオシン関連キナーゼ阻害薬としてのピロロ［２，３−ｄ］ピリミジン誘導体 |
| JP2016509583A (ja) * | 2012-12-21 | 2016-03-31 | プレキシコン インコーポレーテッドＰｌｅｘｘｉｋｏｎ Ｉｎｃ． | キナーゼ調節のための化合物および方法、ならびにその適応 |
| JP2018524381A (ja) * | 2015-07-20 | 2018-08-30 | ジェンザイム・コーポレーション | コロニー刺激因子−１受容体（ｃｓｆ−１ｒ）阻害剤 |
| US11274108B2 (en) | 2015-07-20 | 2022-03-15 | Genzyme Corporation | Colony stimulating factor-1 receptor (CSF-1R) inhibitors |
| JP2019531289A (ja) * | 2016-09-16 | 2019-10-31 | ヘルムホルツ ツェントゥルム ミュンヘン ドイチェス フォルシュングスツェントゥルム フューア ゲズントハイト ウント ウムヴェルト （ゲーエムベーハー） | Ｔｒａｆ６阻害剤 |
| JP7117293B2 (ja) | 2016-09-16 | 2022-08-12 | ヘルムホルツ ツェントゥルム ミュンヘン ドイチェス フォルシュングスツェントゥルム フューア ゲズントハイト ウント ウムヴェルト （ゲーエムベーハー） | Ｔｒａｆ６阻害剤 |
| JP2020524159A (ja) * | 2017-06-19 | 2020-08-13 | アビスコ セラピューティクス カンパニー リミテッド | Ｃｓｆ−１ｒ阻害活性を有するアザアリール誘導体、その製造方法および応用 |
| JP7131837B2 (ja) | 2017-06-19 | 2022-09-06 | アビスコ セラピューティクス カンパニー リミテッド | Ｃｓｆ－１ｒ阻害活性を有するアザアリール誘導体、その製造方法および応用 |
| US11530216B2 (en) | 2020-12-23 | 2022-12-20 | Genzyme Corporation | Deuterated colony stimulating factor-1 receptor (CSF-1R) inhibitors |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1885723A2 (en) | 2008-02-13 |
| AU2006272951A1 (en) | 2007-02-01 |
| CA2608733A1 (en) | 2007-02-01 |
| WO2007013896A3 (en) | 2007-05-31 |
| NZ563444A (en) | 2011-04-29 |
| MX2007014377A (es) | 2008-02-06 |
| CR9591A (es) | 2008-03-26 |
| ECSP077985A (es) | 2008-01-23 |
| US7846941B2 (en) | 2010-12-07 |
| US20110166174A1 (en) | 2011-07-07 |
| BRPI0610066A2 (pt) | 2010-05-25 |
| IL187344A0 (en) | 2008-04-13 |
| WO2007013896A2 (en) | 2007-02-01 |
| KR20080027775A (ko) | 2008-03-28 |
| US20070032519A1 (en) | 2007-02-08 |
| NO20075992L (no) | 2008-02-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2008545652A (ja) | ｃ−ｋｉｔおよびｃ−ｆｍｓ活性を調節する化合物およびその用途 | |
| US10426760B2 (en) | Compounds and methods for kinase modulation, and indications therefor | |
| JP6921846B2 (ja) | キナーゼ調節およびその適応症のための化合物および方法 | |
| EP1893612B1 (en) | Pyrrolo [2, 3-b]pyridine derivatives as protein kinase inhibitors | |
| US7893075B2 (en) | Compounds modulating c-fms and/or c-kit activity and uses therefor | |
| US7872018B2 (en) | Compounds and methods for kinase modulation, and indications therefor | |
| KR20090095654A (ko) | 키나제 조정제로서의 피롤로[２,３-ｂ]피리딘 유도체 | |
| TW201014852A (en) | Indolizine inhibitors of leukotriene production | |
| CN101223169A (zh) | 吡咯并[2,3-b]吡啶衍生物蛋白激酶抑制剂 | |
| HK1174038A (en) | 1h-pyrazolo [ 3, 4-b] pyridine compounds for inhibiting raf kinase | |
| HK1114610B (en) | Pyrrolo [2, 3-b]pyridine derivatives as protein kinase inhibitors |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20090512 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20090512 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20111122 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20111129 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20120424 |