AU2004283162B2 - 2-aminoaryloxazole compounds as tyrosine kinase inhibitors - Google Patents
2-aminoaryloxazole compounds as tyrosine kinase inhibitors Download PDFInfo
- Publication number
- AU2004283162B2 AU2004283162B2 AU2004283162A AU2004283162A AU2004283162B2 AU 2004283162 B2 AU2004283162 B2 AU 2004283162B2 AU 2004283162 A AU2004283162 A AU 2004283162A AU 2004283162 A AU2004283162 A AU 2004283162A AU 2004283162 B2 AU2004283162 B2 AU 2004283162B2
- Authority
- AU
- Australia
- Prior art keywords
- phenyl
- oxazol
- methyl
- pyridin
- ylamino
- 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.)
- Ceased
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 89
- 229940121358 tyrosine kinase inhibitor Drugs 0.000 title description 5
- 239000005483 tyrosine kinase inhibitor Substances 0.000 title description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 30
- 230000000172 allergic effect Effects 0.000 claims abstract description 3
- 208000010668 atopic eczema Diseases 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 120
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 107
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 82
- 229910052794 bromium Inorganic materials 0.000 claims description 63
- 229910052801 chlorine Inorganic materials 0.000 claims description 62
- 229910052731 fluorine Inorganic materials 0.000 claims description 62
- 229910052736 halogen Inorganic materials 0.000 claims description 62
- 229910052740 iodine Inorganic materials 0.000 claims description 57
- 125000003118 aryl group Chemical group 0.000 claims description 51
- 150000002367 halogens Chemical class 0.000 claims description 50
- -1 nitro, formyl Chemical group 0.000 claims description 47
- 229910052739 hydrogen Inorganic materials 0.000 claims description 46
- 125000001072 heteroaryl group Chemical group 0.000 claims description 45
- 229910052757 nitrogen Inorganic materials 0.000 claims description 42
- 239000001257 hydrogen Substances 0.000 claims description 40
- 125000004432 carbon atom Chemical group C* 0.000 claims description 37
- 229910052760 oxygen Inorganic materials 0.000 claims description 37
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 36
- 239000001301 oxygen Substances 0.000 claims description 36
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 34
- 150000002431 hydrogen Chemical class 0.000 claims description 32
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 31
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 30
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 28
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 28
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 27
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
- 201000010099 disease Diseases 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 22
- 239000003814 drug Substances 0.000 claims description 18
- 208000008585 mastocytosis Diseases 0.000 claims description 17
- 206010028980 Neoplasm Diseases 0.000 claims description 14
- 125000005842 heteroatom Chemical group 0.000 claims description 14
- 239000000725 suspension Substances 0.000 claims description 14
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 13
- 125000004076 pyridyl group Chemical group 0.000 claims description 13
- 201000011243 gastrointestinal stromal tumor Diseases 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 125000003282 alkyl amino group Chemical group 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 239000004202 carbamide Substances 0.000 claims description 8
- 125000002541 furyl group Chemical group 0.000 claims description 8
- 125000002883 imidazolyl group Chemical group 0.000 claims description 8
- 125000001041 indolyl group Chemical group 0.000 claims description 8
- 208000027866 inflammatory disease Diseases 0.000 claims description 8
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 8
- 125000002971 oxazolyl group Chemical group 0.000 claims description 8
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 8
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 8
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 8
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 8
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 8
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 8
- 125000000335 thiazolyl group Chemical group 0.000 claims description 8
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- 125000001425 triazolyl group Chemical group 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 239000000499 gel Substances 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 229940080818 propionamide Drugs 0.000 claims description 7
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 7
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 6
- 208000023275 Autoimmune disease Diseases 0.000 claims description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 6
- 208000011580 syndromic disease Diseases 0.000 claims description 6
- 206010051066 Gastrointestinal stromal tumour Diseases 0.000 claims description 5
- 229910003827 NRaRb Inorganic materials 0.000 claims description 5
- 208000026935 allergic disease Diseases 0.000 claims description 5
- 210000000056 organ Anatomy 0.000 claims description 5
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 5
- 208000009329 Graft vs Host Disease Diseases 0.000 claims description 4
- 201000003793 Myelodysplastic syndrome Diseases 0.000 claims description 4
- 208000024780 Urticaria Diseases 0.000 claims description 4
- 239000002537 cosmetic Substances 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 210000004072 lung Anatomy 0.000 claims description 4
- 201000006512 mast cell neoplasm Diseases 0.000 claims description 4
- 208000006971 mastocytoma Diseases 0.000 claims description 4
- 208000028185 Angioedema Diseases 0.000 claims description 3
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 3
- 206010003571 Astrocytoma Diseases 0.000 claims description 3
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims description 3
- 241000282465 Canis Species 0.000 claims description 3
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims description 3
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 3
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 3
- 206010010741 Conjunctivitis Diseases 0.000 claims description 3
- 208000011231 Crohn disease Diseases 0.000 claims description 3
- 201000004624 Dermatitis Diseases 0.000 claims description 3
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 3
- 206010012442 Dermatitis contact Diseases 0.000 claims description 3
- 208000006926 Discoid Lupus Erythematosus Diseases 0.000 claims description 3
- 206010015218 Erythema multiforme Diseases 0.000 claims description 3
- 206010015226 Erythema nodosum Diseases 0.000 claims description 3
- 201000005569 Gout Diseases 0.000 claims description 3
- 206010018634 Gouty Arthritis Diseases 0.000 claims description 3
- 206010061217 Infestation Diseases 0.000 claims description 3
- 208000006877 Insect Bites and Stings Diseases 0.000 claims description 3
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims description 3
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims description 3
- 206010036030 Polyarthritis Diseases 0.000 claims description 3
- 201000004681 Psoriasis Diseases 0.000 claims description 3
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 3
- 208000032384 Severe immune-mediated enteropathy Diseases 0.000 claims description 3
- 208000021386 Sjogren Syndrome Diseases 0.000 claims description 3
- 206010041067 Small cell lung cancer Diseases 0.000 claims description 3
- 201000009594 Systemic Scleroderma Diseases 0.000 claims description 3
- 206010042953 Systemic sclerosis Diseases 0.000 claims description 3
- 208000024313 Testicular Neoplasms Diseases 0.000 claims description 3
- 206010052779 Transplant rejections Diseases 0.000 claims description 3
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 3
- 208000002029 allergic contact dermatitis Diseases 0.000 claims description 3
- 201000010105 allergic rhinitis Diseases 0.000 claims description 3
- 230000002052 anaphylactic effect Effects 0.000 claims description 3
- 206010003230 arteritis Diseases 0.000 claims description 3
- 230000002917 arthritic effect Effects 0.000 claims description 3
- 206010003246 arthritis Diseases 0.000 claims description 3
- 208000006673 asthma Diseases 0.000 claims description 3
- 201000008937 atopic dermatitis Diseases 0.000 claims description 3
- 208000001974 autoimmune enteropathy Diseases 0.000 claims description 3
- 210000004369 blood Anatomy 0.000 claims description 3
- 239000008280 blood Substances 0.000 claims description 3
- 210000001185 bone marrow Anatomy 0.000 claims description 3
- 208000004921 cutaneous lupus erythematosus Diseases 0.000 claims description 3
- 201000001981 dermatomyositis Diseases 0.000 claims description 3
- 206010017758 gastric cancer Diseases 0.000 claims description 3
- 208000010749 gastric carcinoma Diseases 0.000 claims description 3
- 208000005017 glioblastoma Diseases 0.000 claims description 3
- 208000024908 graft versus host disease Diseases 0.000 claims description 3
- 210000002216 heart Anatomy 0.000 claims description 3
- 210000000936 intestine Anatomy 0.000 claims description 3
- 210000003734 kidney Anatomy 0.000 claims description 3
- 210000004185 liver Anatomy 0.000 claims description 3
- 206010025135 lupus erythematosus Diseases 0.000 claims description 3
- 201000006417 multiple sclerosis Diseases 0.000 claims description 3
- 230000002956 necrotizing effect Effects 0.000 claims description 3
- 230000001613 neoplastic effect Effects 0.000 claims description 3
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 3
- 201000008482 osteoarthritis Diseases 0.000 claims description 3
- 210000000496 pancreas Anatomy 0.000 claims description 3
- 230000003071 parasitic effect Effects 0.000 claims description 3
- 208000030428 polyarticular arthritis Diseases 0.000 claims description 3
- 208000005987 polymyositis Diseases 0.000 claims description 3
- 201000008171 proliferative glomerulonephritis Diseases 0.000 claims description 3
- 208000000587 small cell lung carcinoma Diseases 0.000 claims description 3
- 201000000498 stomach carcinoma Diseases 0.000 claims description 3
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 3
- 238000002054 transplantation Methods 0.000 claims description 3
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 3
- VMHVHLSOHUQGSO-UHFFFAOYSA-N 2-methylpropyl n-[4-methyl-3-[(5-pyridin-3-yl-1,3-oxazol-2-yl)amino]phenyl]carbamate Chemical compound CC(C)COC(=O)NC1=CC=C(C)C(NC=2OC(=CN=2)C=2C=NC=CC=2)=C1 VMHVHLSOHUQGSO-UHFFFAOYSA-N 0.000 claims description 2
- 208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims description 2
- 208000014697 Acute lymphocytic leukaemia Diseases 0.000 claims description 2
- 206010005003 Bladder cancer Diseases 0.000 claims description 2
- 206010035226 Plasma cell myeloma Diseases 0.000 claims description 2
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims description 2
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 2
- 239000002775 capsule Substances 0.000 claims description 2
- 239000008298 dragée Substances 0.000 claims description 2
- 201000000050 myeloid neoplasm Diseases 0.000 claims description 2
- MOLNDTKRPCNAPU-UHFFFAOYSA-N n-[5-[[5-(3-iodophenyl)-1,3-oxazol-2-yl]amino]-2-methylphenyl]methanesulfonamide Chemical compound C1=C(NS(C)(=O)=O)C(C)=CC=C1NC1=NC=C(C=2C=C(I)C=CC=2)O1 MOLNDTKRPCNAPU-UHFFFAOYSA-N 0.000 claims description 2
- CKPWPYNTFBAPMP-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-[(5-phenyl-1,3-oxazol-2-yl)amino]benzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1NC(O1)=NC=C1C1=CC=CC=C1 CKPWPYNTFBAPMP-UHFFFAOYSA-N 0.000 claims description 2
- 239000006187 pill Substances 0.000 claims description 2
- 239000002002 slurry Substances 0.000 claims description 2
- 239000006188 syrup Substances 0.000 claims description 2
- 235000020357 syrup Nutrition 0.000 claims description 2
- 239000003826 tablet Substances 0.000 claims description 2
- 238000011200 topical administration Methods 0.000 claims description 2
- 201000005112 urinary bladder cancer Diseases 0.000 claims description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims 4
- 150000001408 amides Chemical class 0.000 claims 2
- GHTDODSYDCPOCW-UHFFFAOYSA-N 1h-indole-6-carboxylic acid Chemical compound OC(=O)C1=CC=C2C=CNC2=C1 GHTDODSYDCPOCW-UHFFFAOYSA-N 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 230000002496 gastric effect Effects 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 201000009890 sinusitis Diseases 0.000 claims 1
- 102000016971 Proto-Oncogene Proteins c-kit Human genes 0.000 abstract description 27
- 108010014608 Proto-Oncogene Proteins c-kit Proteins 0.000 abstract description 27
- 101100335081 Mus musculus Flt3 gene Proteins 0.000 abstract description 15
- 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 abstract description 7
- 102100027842 Fibroblast growth factor receptor 3 Human genes 0.000 abstract description 6
- 101710182396 Fibroblast growth factor receptor 3 Proteins 0.000 abstract description 6
- 239000003112 inhibitor Substances 0.000 abstract description 6
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 abstract description 5
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 abstract description 5
- 230000003389 potentiating effect Effects 0.000 abstract description 5
- 230000019491 signal transduction Effects 0.000 abstract description 4
- 208000031295 Animal disease Diseases 0.000 abstract description 2
- 230000003412 degenerative effect Effects 0.000 abstract description 2
- 230000001404 mediated effect Effects 0.000 abstract description 2
- 230000002503 metabolic effect Effects 0.000 abstract description 2
- 230000002062 proliferating effect Effects 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
- 239000000203 mixture Substances 0.000 description 25
- 239000000243 solution Substances 0.000 description 24
- 238000000034 method Methods 0.000 description 16
- 230000035772 mutation Effects 0.000 description 16
- 210000004027 cell Anatomy 0.000 description 11
- 235000019441 ethanol Nutrition 0.000 description 10
- 210000003630 histaminocyte Anatomy 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 229940079593 drug Drugs 0.000 description 8
- 102000005962 receptors Human genes 0.000 description 8
- 108020003175 receptors Proteins 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 238000009472 formulation Methods 0.000 description 7
- 210000003491 skin Anatomy 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- HSMWDYUWBIZHTQ-UHFFFAOYSA-N 4-methyl-3-n-(5-pyridin-3-yl-1,3-oxazol-2-yl)benzene-1,3-diamine Chemical compound CC1=CC=C(N)C=C1NC1=NC=C(C=2C=NC=CC=2)O1 HSMWDYUWBIZHTQ-UHFFFAOYSA-N 0.000 description 5
- 241000124008 Mammalia Species 0.000 description 5
- 208000002193 Pain Diseases 0.000 description 5
- 108091000080 Phosphotransferase Proteins 0.000 description 5
- 239000000443 aerosol Substances 0.000 description 5
- 239000000969 carrier Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 208000035475 disorder Diseases 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- 208000032839 leukemia Diseases 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 102000020233 phosphotransferase Human genes 0.000 description 5
- 102000004169 proteins and genes Human genes 0.000 description 5
- 108090000623 proteins and genes Proteins 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 4
- 241001529936 Murinae Species 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 238000003556 assay Methods 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- 208000015181 infectious disease Diseases 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000003755 preservative agent Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- 208000011117 substance-related disease Diseases 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 230000004083 survival effect Effects 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- NAMNJFIYPVILSQ-UHFFFAOYSA-N 2-azido-1-pyridin-3-ylethanone Chemical compound [N-]=[N+]=NCC(=O)C1=CC=CN=C1 NAMNJFIYPVILSQ-UHFFFAOYSA-N 0.000 description 3
- QQGKEUWTCWSWIM-UHFFFAOYSA-N 3-(dimethylamino)-n-[4-methyl-3-[(5-pyridin-3-yl-1,3-oxazol-2-yl)amino]phenyl]benzamide Chemical compound CN(C)C1=CC=CC(C(=O)NC=2C=C(NC=3OC(=CN=3)C=3C=NC=CC=3)C(C)=CC=2)=C1 QQGKEUWTCWSWIM-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 206010065687 Bone loss Diseases 0.000 description 3
- 206010016654 Fibrosis Diseases 0.000 description 3
- 208000005615 Interstitial Cystitis Diseases 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 201000008736 Systemic mastocytosis Diseases 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000002159 abnormal effect Effects 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 3
- 239000012300 argon atmosphere Substances 0.000 description 3
- 208000015114 central nervous system disease Diseases 0.000 description 3
- 239000006071 cream Substances 0.000 description 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 3
- 238000012217 deletion Methods 0.000 description 3
- 230000037430 deletion Effects 0.000 description 3
- 206010012601 diabetes mellitus Diseases 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 230000002708 enhancing effect Effects 0.000 description 3
- 230000004761 fibrosis Effects 0.000 description 3
- 239000003349 gelling agent Substances 0.000 description 3
- 230000003211 malignant effect Effects 0.000 description 3
- 208000030159 metabolic disease Diseases 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 230000035755 proliferation Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- 230000005747 tumor angiogenesis Effects 0.000 description 3
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 2
- WEGYGNROSJDEIW-UHFFFAOYSA-N 3-Acetylpyridine Chemical compound CC(=O)C1=CC=CN=C1 WEGYGNROSJDEIW-UHFFFAOYSA-N 0.000 description 2
- 206010000830 Acute leukaemia Diseases 0.000 description 2
- 206010001488 Aggression Diseases 0.000 description 2
- 206010049153 Allergic sinusitis Diseases 0.000 description 2
- 208000000044 Amnesia Diseases 0.000 description 2
- 208000019901 Anxiety disease Diseases 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 208000035143 Bacterial infection Diseases 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- 241000283707 Capra Species 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 108091026890 Coding region Proteins 0.000 description 2
- 208000006343 Cutaneous Mastocytosis Diseases 0.000 description 2
- 108090000695 Cytokines Proteins 0.000 description 2
- 102000004127 Cytokines Human genes 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- 108010002386 Interleukin-3 Proteins 0.000 description 2
- 102100039064 Interleukin-3 Human genes 0.000 description 2
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical group OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 2
- 102100027754 Mast/stem cell growth factor receptor Kit Human genes 0.000 description 2
- 208000026072 Motor neurone disease Diseases 0.000 description 2
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 229940124639 Selective inhibitor Drugs 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- 206010064127 Solar lentigo Diseases 0.000 description 2
- IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 description 2
- 230000003213 activating effect Effects 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 229920013820 alkyl cellulose Polymers 0.000 description 2
- POJWUDADGALRAB-UHFFFAOYSA-N allantoin Chemical compound NC(=O)NC1NC(=O)NC1=O POJWUDADGALRAB-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 208000022362 bacterial infectious disease Diseases 0.000 description 2
- IQFYYKKMVGJFEH-UHFFFAOYSA-N beta-L-thymidine Natural products O=C1NC(=O)C(C)=CN1C1OC(CO)C(O)C1 IQFYYKKMVGJFEH-UHFFFAOYSA-N 0.000 description 2
- 239000000872 buffer 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
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 230000004663 cell proliferation Effects 0.000 description 2
- 238000001516 cell proliferation assay Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 230000006552 constitutive activation Effects 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 230000004064 dysfunction Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000003623 enhancer Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 230000003394 haemopoietic effect Effects 0.000 description 2
- 208000014951 hematologic disease Diseases 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000003906 humectant Substances 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 230000008595 infiltration Effects 0.000 description 2
- 238000001764 infiltration Methods 0.000 description 2
- 230000002757 inflammatory effect Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 231100000518 lethal Toxicity 0.000 description 2
- 230000001665 lethal effect Effects 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 208000000516 mast-cell leukemia Diseases 0.000 description 2
- 210000002752 melanocyte Anatomy 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 235000010981 methylcellulose Nutrition 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- LDIWYEZYXJYWAX-UHFFFAOYSA-N n-(2-methyl-5-nitrophenyl)-5-pyridin-3-yl-1,3-oxazol-2-amine Chemical compound CC1=CC=C([N+]([O-])=O)C=C1NC1=NC=C(C=2C=NC=CC=2)O1 LDIWYEZYXJYWAX-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 208000002851 paranoid schizophrenia Diseases 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 208000019899 phobic disease Diseases 0.000 description 2
- 239000000419 plant extract Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000004393 prognosis Methods 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000000241 respiratory effect Effects 0.000 description 2
- 210000002345 respiratory system Anatomy 0.000 description 2
- 201000000980 schizophrenia Diseases 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 230000026683 transduction Effects 0.000 description 2
- 238000010361 transduction Methods 0.000 description 2
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
- 150000004917 tyrosine kinase inhibitor derivatives Chemical class 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- 238000001262 western blot Methods 0.000 description 2
- LLKMLSXETYSLPE-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[4-methyl-3-[(5-pyridin-3-yl-1,3-oxazol-2-yl)amino]phenyl]urea Chemical compound C1=C(NC=2OC(=CN=2)C=2C=NC=CC=2)C(C)=CC=C1NC(=O)NC1=CC=C(Cl)C=C1 LLKMLSXETYSLPE-UHFFFAOYSA-N 0.000 description 1
- BGQHVFBHLADCQZ-UHFFFAOYSA-N 1-(4-cyanophenyl)-3-[4-methyl-3-[(5-pyridin-3-yl-1,3-oxazol-2-yl)amino]phenyl]thiourea Chemical compound C1=C(NC=2OC(=CN=2)C=2C=NC=CC=2)C(C)=CC=C1NC(=S)NC1=CC=C(C#N)C=C1 BGQHVFBHLADCQZ-UHFFFAOYSA-N 0.000 description 1
- BAVXBJWGPLEKED-UHFFFAOYSA-N 1-(4-cyanophenyl)-3-[4-methyl-3-[(5-pyridin-3-yl-1,3-oxazol-2-yl)amino]phenyl]urea Chemical compound C1=C(NC=2OC(=CN=2)C=2C=NC=CC=2)C(C)=CC=C1NC(=O)NC1=CC=C(C#N)C=C1 BAVXBJWGPLEKED-UHFFFAOYSA-N 0.000 description 1
- PLQYBDZYCAXEDV-UHFFFAOYSA-N 1-(4-cyanophenyl)-3-[4-methyl-3-[(5-pyridin-4-yl-1,3-oxazol-2-yl)amino]phenyl]thiourea Chemical compound C1=C(NC=2OC(=CN=2)C=2C=CN=CC=2)C(C)=CC=C1NC(=S)NC1=CC=C(C#N)C=C1 PLQYBDZYCAXEDV-UHFFFAOYSA-N 0.000 description 1
- NTOGTTYFZKYUPA-UHFFFAOYSA-N 1-(4-fluorophenyl)-3-[4-methyl-3-[(5-pyridin-3-yl-1,3-oxazol-2-yl)amino]phenyl]urea Chemical compound C1=C(NC=2OC(=CN=2)C=2C=NC=CC=2)C(C)=CC=C1NC(=O)NC1=CC=C(F)C=C1 NTOGTTYFZKYUPA-UHFFFAOYSA-N 0.000 description 1
- KZFOFDORPQTDHN-UHFFFAOYSA-N 1-(4-methylphenyl)-3-[4-methyl-3-[(5-pyridin-3-yl-1,3-oxazol-2-yl)amino]phenyl]urea Chemical compound C1=CC(C)=CC=C1NC(=O)NC1=CC=C(C)C(NC=2OC(=CN=2)C=2C=NC=CC=2)=C1 KZFOFDORPQTDHN-UHFFFAOYSA-N 0.000 description 1
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
- CGCLXYGIXNAGFW-UHFFFAOYSA-N 1-benzyl-3-[4-methyl-3-[(5-pyridin-4-yl-1,3-oxazol-2-yl)amino]phenyl]thiourea Chemical compound C1=C(NC=2OC(=CN=2)C=2C=CN=CC=2)C(C)=CC=C1NC(=S)NCC1=CC=CC=C1 CGCLXYGIXNAGFW-UHFFFAOYSA-N 0.000 description 1
- AXTGDCSMTYGJND-UHFFFAOYSA-N 1-dodecylazepan-2-one Chemical compound CCCCCCCCCCCCN1CCCCCC1=O AXTGDCSMTYGJND-UHFFFAOYSA-N 0.000 description 1
- NZJXADCEESMBPW-UHFFFAOYSA-N 1-methylsulfinyldecane Chemical compound CCCCCCCCCCS(C)=O NZJXADCEESMBPW-UHFFFAOYSA-N 0.000 description 1
- YSUBMVSDUMNSNS-UHFFFAOYSA-N 1-n-(1,3-benzoxazol-2-yl)-4-methyl-3-n-(5-pyridin-4-yl-1,3-oxazol-2-yl)benzene-1,3-diamine Chemical compound CC1=CC=C(NC=2OC3=CC=CC=C3N=2)C=C1NC(O1)=NC=C1C1=CC=NC=C1 YSUBMVSDUMNSNS-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- KEEBUCPGLVETKH-UHFFFAOYSA-N 2-(3-methylphenyl)-n-[4-methyl-3-[(5-pyridin-4-yl-1,3-oxazol-2-yl)amino]phenyl]acetamide Chemical compound CC1=CC=CC(CC(=O)NC=2C=C(NC=3OC(=CN=3)C=3C=CN=CC=3)C(C)=CC=2)=C1 KEEBUCPGLVETKH-UHFFFAOYSA-N 0.000 description 1
- CLLCSCDTYOIJHO-UHFFFAOYSA-N 2-(4-methoxyphenyl)-n-[4-methyl-3-[(5-pyridin-4-yl-1,3-oxazol-2-yl)amino]phenyl]acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)NC1=CC=C(C)C(NC=2OC(=CN=2)C=2C=CN=CC=2)=C1 CLLCSCDTYOIJHO-UHFFFAOYSA-N 0.000 description 1
- UKAUVLQLNKBSKS-UHFFFAOYSA-N 2-[3-(1,3-oxazol-2-ylamino)phenyl]acetamide Chemical compound NC(=O)CC1=CC=CC(NC=2OC=CN=2)=C1 UKAUVLQLNKBSKS-UHFFFAOYSA-N 0.000 description 1
- IQMGXSROJBYCLS-UHFFFAOYSA-N 2-bromo-1-pyridin-3-ylethanone Chemical compound BrCC(=O)C1=CC=CN=C1 IQMGXSROJBYCLS-UHFFFAOYSA-N 0.000 description 1
- WDTSYONULAZKIE-UHFFFAOYSA-N 2-bromo-1-pyridin-3-ylethanone;hydron;bromide Chemical compound [Br-].BrCC(=O)C1=CC=C[NH+]=C1 WDTSYONULAZKIE-UHFFFAOYSA-N 0.000 description 1
- MTDSANYYCBYFOZ-UHFFFAOYSA-N 2-cyano-n-[4-methyl-3-[(5-pyridin-4-yl-1,3-oxazol-2-yl)amino]phenyl]acetamide Chemical compound CC1=CC=C(NC(=O)CC#N)C=C1NC1=NC=C(C=2C=CN=CC=2)O1 MTDSANYYCBYFOZ-UHFFFAOYSA-N 0.000 description 1
- CBRSXJFHARVENS-UHFFFAOYSA-N 2-ethoxy-n-[4-methyl-3-[(5-pyridin-3-yl-1,3-oxazol-2-yl)amino]phenyl]acetamide Chemical compound CCOCC(=O)NC1=CC=C(C)C(NC=2OC(=CN=2)C=2C=NC=CC=2)=C1 CBRSXJFHARVENS-UHFFFAOYSA-N 0.000 description 1
- RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 1
- PQFOUIMVTGBFRN-UHFFFAOYSA-N 2-isocyanato-1-methyl-4-nitrobenzene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1N=C=O PQFOUIMVTGBFRN-UHFFFAOYSA-N 0.000 description 1
- IGLZHUHGTKHGHJ-UHFFFAOYSA-N 2-methylpropyl n-[2-methyl-5-(2-methylpropoxycarbonylamino)phenyl]-n-(5-pyridin-3-yl-1,3-oxazol-2-yl)carbamate Chemical compound CC(C)COC(=O)NC1=CC=C(C)C(N(C(=O)OCC(C)C)C=2OC(=CN=2)C=2C=NC=CC=2)=C1 IGLZHUHGTKHGHJ-UHFFFAOYSA-N 0.000 description 1
- VCQMPUPEARTEGT-UHFFFAOYSA-N 2-methylpropyl n-[4-methyl-3-[(5-pyridin-4-yl-1,3-oxazol-2-yl)amino]phenyl]carbamate Chemical compound CC(C)COC(=O)NC1=CC=C(C)C(NC=2OC(=CN=2)C=2C=CN=CC=2)=C1 VCQMPUPEARTEGT-UHFFFAOYSA-N 0.000 description 1
- LKKCHGMMTKHEQP-UHFFFAOYSA-N 3-(1,3-oxazol-2-ylamino)benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC(NC=2OC=CN=2)=C1 LKKCHGMMTKHEQP-UHFFFAOYSA-N 0.000 description 1
- RYCSNJCJOVQGBC-UHFFFAOYSA-N 3-(1-cyclopropyl-2h-pyridin-4-yl)-1h-quinolin-2-one Chemical class O=C1NC2=CC=CC=C2C=C1C(C=C1)=CCN1C1CC1 RYCSNJCJOVQGBC-UHFFFAOYSA-N 0.000 description 1
- NEGFNJRAUMCZMY-UHFFFAOYSA-N 3-(dimethylamino)benzoic acid Chemical compound CN(C)C1=CC=CC(C(O)=O)=C1 NEGFNJRAUMCZMY-UHFFFAOYSA-N 0.000 description 1
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
- BGXXLKNLLJELND-UHFFFAOYSA-N 3-N-(1,3-oxazol-2-yl)benzene-1,3-diamine Chemical compound NC1=CC=CC(NC=2OC=CN=2)=C1 BGXXLKNLLJELND-UHFFFAOYSA-N 0.000 description 1
- CFSOZHKOFYGOJX-UHFFFAOYSA-N 3-bromo-n-[4-methyl-3-[(5-pyridin-3-yl-1,3-oxazol-2-yl)amino]phenyl]benzamide Chemical compound C1=C(NC=2OC(=CN=2)C=2C=NC=CC=2)C(C)=CC=C1NC(=O)C1=CC=CC(Br)=C1 CFSOZHKOFYGOJX-UHFFFAOYSA-N 0.000 description 1
- IFZBJUUFHJRIQE-UHFFFAOYSA-N 3-fluoro-4-[(4-methylpiperazin-1-yl)methyl]-n-[4-methyl-3-[(5-pyridin-3-yl-1,3-oxazol-2-yl)amino]phenyl]benzamide Chemical compound C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3OC(=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1F IFZBJUUFHJRIQE-UHFFFAOYSA-N 0.000 description 1
- YBAZINRZQSAIAY-UHFFFAOYSA-N 4-aminobenzonitrile Chemical compound NC1=CC=C(C#N)C=C1 YBAZINRZQSAIAY-UHFFFAOYSA-N 0.000 description 1
- LUBJFLBNBALVMZ-UHFFFAOYSA-N 4-methyl-1-n-(5-phenyl-1,3,4-oxadiazol-2-yl)-3-n-(5-pyridin-4-yl-1,3-oxazol-2-yl)benzene-1,3-diamine Chemical compound C1=C(NC=2OC(=CN=2)C=2C=CN=CC=2)C(C)=CC=C1NC(O1)=NN=C1C1=CC=CC=C1 LUBJFLBNBALVMZ-UHFFFAOYSA-N 0.000 description 1
- LLRWNDWHVNPUMJ-UHFFFAOYSA-N 4-methyl-1-n-(5-phenyl-1,3-oxazol-2-yl)-3-n-(5-pyridin-4-yl-1,3-oxazol-2-yl)benzene-1,3-diamine Chemical compound C1=C(NC=2OC(=CN=2)C=2C=CN=CC=2)C(C)=CC=C1NC(O1)=NC=C1C1=CC=CC=C1 LLRWNDWHVNPUMJ-UHFFFAOYSA-N 0.000 description 1
- CBOXAKYSTSFXTD-UHFFFAOYSA-N 4-methyl-1-n-(5-pyridin-3-yl-1,3-oxazol-2-yl)-3-n-(5-pyridin-4-yl-1,3-oxazol-2-yl)benzene-1,3-diamine Chemical compound C1=C(NC=2OC(=CN=2)C=2C=CN=CC=2)C(C)=CC=C1NC(O1)=NC=C1C1=CC=CN=C1 CBOXAKYSTSFXTD-UHFFFAOYSA-N 0.000 description 1
- TXHCAUUNNPYFJD-UHFFFAOYSA-N 4-methyl-n-[4-methyl-3-[(5-pyridin-3-yl-1,3-oxazol-2-yl)amino]phenyl]pentanamide Chemical compound CC(C)CCC(=O)NC1=CC=C(C)C(NC=2OC(=CN=2)C=2C=NC=CC=2)=C1 TXHCAUUNNPYFJD-UHFFFAOYSA-N 0.000 description 1
- CEUWQPLATDRHEL-UHFFFAOYSA-N 4-n-[4-methyl-3-[(5-pyridin-3-yl-1,3-oxazol-2-yl)amino]phenyl]benzene-1,4-dicarboxamide Chemical compound C1=C(NC=2OC(=CN=2)C=2C=NC=CC=2)C(C)=CC=C1NC(=O)C1=CC=C(C(N)=O)C=C1 CEUWQPLATDRHEL-UHFFFAOYSA-N 0.000 description 1
- LGZSXFUMYWZFGV-UHFFFAOYSA-N 5-methyl-n-[4-methyl-3-[(5-pyridin-4-yl-1,3-oxazol-2-yl)amino]phenyl]-1,2-oxazole-4-carboxamide Chemical compound O1N=CC(C(=O)NC=2C=C(NC=3OC(=CN=3)C=3C=CN=CC=3)C(C)=CC=2)=C1C LGZSXFUMYWZFGV-UHFFFAOYSA-N 0.000 description 1
- USVZHTBPMMSRHY-UHFFFAOYSA-N 8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-9-[2-(2-chlorophenyl)ethyl]purin-6-amine Chemical class C=1C=2OCOC=2C=C(Br)C=1SC1=NC=2C(N)=NC=NC=2N1CCC1=CC=CC=C1Cl USVZHTBPMMSRHY-UHFFFAOYSA-N 0.000 description 1
- 208000002874 Acne Vulgaris Diseases 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 206010001022 Acute psychosis Diseases 0.000 description 1
- 201000008217 Aggressive systemic mastocytosis Diseases 0.000 description 1
- POJWUDADGALRAB-PVQJCKRUSA-N Allantoin Natural products NC(=O)N[C@@H]1NC(=O)NC1=O POJWUDADGALRAB-PVQJCKRUSA-N 0.000 description 1
- 244000144927 Aloe barbadensis Species 0.000 description 1
- 235000002961 Aloe barbadensis Nutrition 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 108010001478 Bacitracin Proteins 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 229940118364 Bcr-Abl inhibitor Drugs 0.000 description 1
- OGBVRMYSNSKIEF-UHFFFAOYSA-N Benzylphosphonic acid Chemical class OP(O)(=O)CC1=CC=CC=C1 OGBVRMYSNSKIEF-UHFFFAOYSA-N 0.000 description 1
- 208000020925 Bipolar disease Diseases 0.000 description 1
- 201000006474 Brain Ischemia Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 208000032841 Bulimia Diseases 0.000 description 1
- 206010006550 Bulimia nervosa Diseases 0.000 description 1
- 206010058019 Cancer Pain Diseases 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 208000009810 Catatonic Schizophrenia Diseases 0.000 description 1
- 229930186147 Cephalosporin Natural products 0.000 description 1
- 206010008120 Cerebral ischaemia Diseases 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- 206010008874 Chronic Fatigue Syndrome Diseases 0.000 description 1
- 206010008909 Chronic Hepatitis Diseases 0.000 description 1
- 208000000094 Chronic Pain Diseases 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- 235000010919 Copernicia prunifera Nutrition 0.000 description 1
- 244000180278 Copernicia prunifera Species 0.000 description 1
- 108010092160 Dactinomycin Proteins 0.000 description 1
- XMSXQFUHVRWGNA-UHFFFAOYSA-N Decamethylcyclopentasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 XMSXQFUHVRWGNA-UHFFFAOYSA-N 0.000 description 1
- 206010012218 Delirium Diseases 0.000 description 1
- 208000024254 Delusional disease Diseases 0.000 description 1
- 206010012335 Dependence Diseases 0.000 description 1
- 208000032538 Depersonalisation Diseases 0.000 description 1
- 206010012812 Diffuse cutaneous mastocytosis Diseases 0.000 description 1
- 206010061818 Disease progression Diseases 0.000 description 1
- 208000001495 Disorganized Schizophrenia Diseases 0.000 description 1
- 208000025967 Dissociative Identity disease Diseases 0.000 description 1
- 208000035713 Dissociative fugue Diseases 0.000 description 1
- 206010013654 Drug abuse Diseases 0.000 description 1
- 206010013801 Duchenne Muscular Dystrophy Diseases 0.000 description 1
- 208000032928 Dyslipidaemia Diseases 0.000 description 1
- 241000305071 Enterobacterales Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 108091008794 FGF receptors Proteins 0.000 description 1
- 102100020715 Fms-related tyrosine kinase 3 ligand protein Human genes 0.000 description 1
- 101710162577 Fms-related tyrosine kinase 3 ligand protein Proteins 0.000 description 1
- 208000011688 Generalised anxiety disease Diseases 0.000 description 1
- 108010017213 Granulocyte-Macrophage Colony-Stimulating Factor Proteins 0.000 description 1
- 102100039620 Granulocyte-macrophage colony-stimulating factor Human genes 0.000 description 1
- 208000031886 HIV Infections Diseases 0.000 description 1
- 208000037357 HIV infectious disease Diseases 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 101001008874 Homo sapiens Mast/stem cell growth factor receptor Kit Proteins 0.000 description 1
- 208000023105 Huntington disease Diseases 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- 208000031226 Hyperlipidaemia Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 108010002352 Interleukin-1 Proteins 0.000 description 1
- 108010002350 Interleukin-2 Proteins 0.000 description 1
- 108090000978 Interleukin-4 Proteins 0.000 description 1
- 108010002616 Interleukin-5 Proteins 0.000 description 1
- 108090001005 Interleukin-6 Proteins 0.000 description 1
- 108090001007 Interleukin-8 Proteins 0.000 description 1
- 241000588747 Klebsiella pneumoniae Species 0.000 description 1
- 125000003580 L-valyl group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C(C([H])([H])[H])(C([H])([H])[H])[H] 0.000 description 1
- 206010026749 Mania Diseases 0.000 description 1
- 208000003351 Melanosis Diseases 0.000 description 1
- 208000026139 Memory disease Diseases 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 101710151803 Mitochondrial intermediate peptidase 2 Proteins 0.000 description 1
- 208000029578 Muscle disease Diseases 0.000 description 1
- 208000021642 Muscular disease Diseases 0.000 description 1
- 208000014767 Myeloproliferative disease Diseases 0.000 description 1
- 201000007224 Myeloproliferative neoplasm Diseases 0.000 description 1
- 102100024007 Neurofilament heavy polypeptide Human genes 0.000 description 1
- 102000035092 Neutral proteases Human genes 0.000 description 1
- 108091005507 Neutral proteases Proteins 0.000 description 1
- 208000001294 Nociceptive Pain Diseases 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 206010033664 Panic attack Diseases 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- 241000721454 Pemphigus Species 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 206010034912 Phobia Diseases 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 208000004550 Postoperative Pain Diseases 0.000 description 1
- 206010036618 Premenstrual syndrome Diseases 0.000 description 1
- 208000024777 Prion disease Diseases 0.000 description 1
- 239000004365 Protease Substances 0.000 description 1
- 108010009736 Protein Hydrolysates Proteins 0.000 description 1
- 208000028017 Psychotic disease Diseases 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
- 241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 description 1
- 208000036754 Schizophrenia, catatonic type Diseases 0.000 description 1
- 208000036752 Schizophrenia, paranoid type Diseases 0.000 description 1
- 241000607715 Serratia marcescens Species 0.000 description 1
- 206010040865 Skin hyperpigmentation Diseases 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 208000035286 Spontaneous Remission Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 description 1
- 206010065604 Suicidal behaviour Diseases 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- 239000004098 Tetracycline Substances 0.000 description 1
- 208000031674 Traumatic Acute Stress disease Diseases 0.000 description 1
- 208000028552 Treatment-Resistant Depressive disease Diseases 0.000 description 1
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 1
- 102100040247 Tumor necrosis factor Human genes 0.000 description 1
- 206010046752 Urticaria Pigmentosa Diseases 0.000 description 1
- 108091008605 VEGF receptors Proteins 0.000 description 1
- 102000009484 Vascular Endothelial Growth Factor Receptors Human genes 0.000 description 1
- 206010047115 Vasculitis Diseases 0.000 description 1
- FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- 235000018936 Vitellaria paradoxa Nutrition 0.000 description 1
- 241001135917 Vitellaria paradoxa Species 0.000 description 1
- 206010048010 Withdrawal syndrome Diseases 0.000 description 1
- MFUFHZKKPQILKN-UHFFFAOYSA-N [3-(1,3-oxazol-2-ylamino)phenyl]carbamic acid Chemical compound OC(=O)NC1=CC=CC(NC=2OC=CN=2)=C1 MFUFHZKKPQILKN-UHFFFAOYSA-N 0.000 description 1
- FCIROYMMAHUDFI-UHFFFAOYSA-N [3-(1,3-oxazol-2-ylamino)phenyl]thiourea Chemical compound NC(=S)NC1=CC=CC(NC=2OC=CN=2)=C1 FCIROYMMAHUDFI-UHFFFAOYSA-N 0.000 description 1
- MGJAKLSGRBMOLQ-UHFFFAOYSA-N [3-(1,3-oxazol-2-ylamino)phenyl]urea Chemical compound NC(=O)NC1=CC=CC(NC=2OC=CN=2)=C1 MGJAKLSGRBMOLQ-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 206010000496 acne Diseases 0.000 description 1
- 229920006243 acrylic copolymer Polymers 0.000 description 1
- 229920000800 acrylic rubber Polymers 0.000 description 1
- 229930183665 actinomycin Natural products 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 208000005298 acute pain Diseases 0.000 description 1
- 208000026345 acute stress disease Diseases 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229960000458 allantoin Drugs 0.000 description 1
- 235000011399 aloe vera Nutrition 0.000 description 1
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical class [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
- 229940126575 aminoglycoside Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 208000022531 anorexia Diseases 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 239000008365 aqueous carrier Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000010692 aromatic oil Substances 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 208000025748 atypical depressive disease Diseases 0.000 description 1
- 230000001363 autoimmune Effects 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 229960003071 bacitracin Drugs 0.000 description 1
- 229930184125 bacitracin Natural products 0.000 description 1
- CLKOFPXJLQSYAH-ABRJDSQDSA-N bacitracin A Chemical compound C1SC([C@@H](N)[C@@H](C)CC)=N[C@@H]1C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]1C(=O)N[C@H](CCCN)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2N=CNC=2)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)NCCCC1 CLKOFPXJLQSYAH-ABRJDSQDSA-N 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 208000028683 bipolar I disease Diseases 0.000 description 1
- 208000025307 bipolar depression Diseases 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 208000030963 borderline personality disease Diseases 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 229960001631 carbomer Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 206010007776 catatonia Diseases 0.000 description 1
- 230000011712 cell development Effects 0.000 description 1
- 239000013592 cell lysate Substances 0.000 description 1
- 230000012292 cell migration Effects 0.000 description 1
- 230000007248 cellular mechanism Effects 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- 229940106189 ceramide Drugs 0.000 description 1
- 150000001783 ceramides Chemical class 0.000 description 1
- 206010008118 cerebral infarction Diseases 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 208000030242 cutaneous mastocytoma Diseases 0.000 description 1
- 201000006515 cutaneous solitary mastocytoma Diseases 0.000 description 1
- 229940086555 cyclomethicone Drugs 0.000 description 1
- 208000026725 cyclothymic disease Diseases 0.000 description 1
- 201000003146 cystitis Diseases 0.000 description 1
- 230000001086 cytosolic effect Effects 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 239000000850 decongestant Substances 0.000 description 1
- 206010061428 decreased appetite Diseases 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000000779 depleting effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000005750 disease progression Effects 0.000 description 1
- 206010013461 dissociative amnesia Diseases 0.000 description 1
- SYELZBGXAIXKHU-UHFFFAOYSA-N dodecyldimethylamine N-oxide Chemical compound CCCCCCCCCCCC[N+](C)(C)[O-] SYELZBGXAIXKHU-UHFFFAOYSA-N 0.000 description 1
- 206010013663 drug dependence Diseases 0.000 description 1
- 208000024732 dysthymic disease Diseases 0.000 description 1
- 239000003974 emollient agent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 210000002615 epidermis Anatomy 0.000 description 1
- 229960003276 erythromycin Drugs 0.000 description 1
- 235000004626 essential fatty acids Nutrition 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 102000052178 fibroblast growth factor receptor activity proteins Human genes 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 108091071773 flk family Proteins 0.000 description 1
- 229940124307 fluoroquinolone Drugs 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- 208000029364 generalized anxiety disease Diseases 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 235000013773 glyceryl triacetate Nutrition 0.000 description 1
- 239000001087 glyceryl triacetate Substances 0.000 description 1
- 229940100242 glycol stearate Drugs 0.000 description 1
- 239000003102 growth factor Substances 0.000 description 1
- 210000003958 hematopoietic stem cell Anatomy 0.000 description 1
- 208000006454 hepatitis Diseases 0.000 description 1
- IIRDTKBZINWQAW-UHFFFAOYSA-N hexaethylene glycol Chemical compound OCCOCCOCCOCCOCCOCCO IIRDTKBZINWQAW-UHFFFAOYSA-N 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 102000055152 human KIT Human genes 0.000 description 1
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 208000000069 hyperpigmentation Diseases 0.000 description 1
- 208000000122 hyperventilation Diseases 0.000 description 1
- 230000000870 hyperventilation Effects 0.000 description 1
- 238000001114 immunoprecipitation Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000000415 inactivating effect Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000002563 ionic surfactant Substances 0.000 description 1
- 230000000622 irritating effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 206010024217 lentigo Diseases 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 210000004698 lymphocyte Anatomy 0.000 description 1
- 230000000527 lymphocytic effect Effects 0.000 description 1
- 239000003120 macrolide antibiotic agent Substances 0.000 description 1
- 208000030179 maculopapular cutaneous mastocytosis Diseases 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- 239000002583 male contraceptive agent Substances 0.000 description 1
- 210000004962 mammalian cell Anatomy 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- 230000006984 memory degeneration Effects 0.000 description 1
- 208000023060 memory loss Diseases 0.000 description 1
- 230000009245 menopause Effects 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 239000013081 microcrystal Substances 0.000 description 1
- 239000011859 microparticle Substances 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 230000003020 moisturizing effect Effects 0.000 description 1
- 208000027881 multiple personality disease Diseases 0.000 description 1
- 208000029766 myalgic encephalomeyelitis/chronic fatigue syndrome Diseases 0.000 description 1
- 230000002071 myeloproliferative effect Effects 0.000 description 1
- HOWLHUUPCSMTAZ-UHFFFAOYSA-N n-(3-chlorophenyl)-4-methyl-3-[(5-pyridin-3-yl-1,3-oxazol-2-yl)amino]benzamide Chemical compound CC1=CC=C(C(=O)NC=2C=C(Cl)C=CC=2)C=C1NC(O1)=NC=C1C1=CC=CN=C1 HOWLHUUPCSMTAZ-UHFFFAOYSA-N 0.000 description 1
- BLAFNVLTEJJENP-UHFFFAOYSA-N n-(4-cyanophenyl)-4-methyl-3-[(5-pyridin-3-yl-1,3-oxazol-2-yl)amino]benzamide Chemical compound CC1=CC=C(C(=O)NC=2C=CC(=CC=2)C#N)C=C1NC(O1)=NC=C1C1=CC=CN=C1 BLAFNVLTEJJENP-UHFFFAOYSA-N 0.000 description 1
- CEATXLYGLKXKBX-UHFFFAOYSA-N n-[3-[[5-(4-cyanophenyl)-1,3-oxazol-2-yl]amino]-4-methylphenyl]-2-(2,4-difluorophenyl)acetamide Chemical compound C1=C(NC=2OC(=CN=2)C=2C=CC(=CC=2)C#N)C(C)=CC=C1NC(=O)CC1=CC=C(F)C=C1F CEATXLYGLKXKBX-UHFFFAOYSA-N 0.000 description 1
- XIZNQJMQUBYUJV-UHFFFAOYSA-N n-[4-methoxy-3-[(5-pyridin-4-yl-1,3-oxazol-2-yl)amino]phenyl]-2-[4-(trifluoromethyl)phenyl]acetamide Chemical compound C1=C(NC=2OC(=CN=2)C=2C=CN=CC=2)C(OC)=CC=C1NC(=O)CC1=CC=C(C(F)(F)F)C=C1 XIZNQJMQUBYUJV-UHFFFAOYSA-N 0.000 description 1
- MBXJCNACGQESRD-UHFFFAOYSA-N n-[4-methyl-3-[(5-pyridin-3-yl-1,3-oxazol-2-yl)amino]phenyl]-2-piperazin-1-ylacetamide Chemical compound C1=C(NC=2OC(=CN=2)C=2C=NC=CC=2)C(C)=CC=C1NC(=O)CN1CCNCC1 MBXJCNACGQESRD-UHFFFAOYSA-N 0.000 description 1
- WTHMHBCPQRFUBK-UHFFFAOYSA-N n-[4-methyl-3-[(5-pyridin-3-yl-1,3-oxazol-2-yl)amino]phenyl]acetamide Chemical compound CC(=O)NC1=CC=C(C)C(NC=2OC(=CN=2)C=2C=NC=CC=2)=C1 WTHMHBCPQRFUBK-UHFFFAOYSA-N 0.000 description 1
- FDAHBOFXYSTPOL-UHFFFAOYSA-N n-[4-methyl-3-[(5-pyridin-4-yl-1,3-oxazol-2-yl)amino]phenyl]-1h-indole-6-carboxamide Chemical compound CC1=CC=C(NC(=O)C=2C=C3NC=CC3=CC=2)C=C1NC(O1)=NC=C1C1=CC=NC=C1 FDAHBOFXYSTPOL-UHFFFAOYSA-N 0.000 description 1
- HORDAYGVVWNPQO-UHFFFAOYSA-N n-benzyl-4-methyl-3-[(5-pyridin-4-yl-1,3-oxazol-2-yl)amino]benzamide Chemical compound CC1=CC=C(C(=O)NCC=2C=CC=CC=2)C=C1NC(O1)=NC=C1C1=CC=NC=C1 HORDAYGVVWNPQO-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 229920001206 natural gum Polymers 0.000 description 1
- 208000004296 neuralgia Diseases 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 108010091047 neurofilament protein H Proteins 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 208000021722 neuropathic pain Diseases 0.000 description 1
- 229960001730 nitrous oxide Drugs 0.000 description 1
- 235000013842 nitrous oxide Nutrition 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- 208000019906 panic disease Diseases 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 229940119519 peg-32 stearate Drugs 0.000 description 1
- 239000003961 penetration enhancing agent Substances 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 210000005259 peripheral blood Anatomy 0.000 description 1
- 239000011886 peripheral blood Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000059 polyethylene glycol stearate Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229940113124 polysorbate 60 Drugs 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 238000010837 poor prognosis Methods 0.000 description 1
- 208000028173 post-traumatic stress disease Diseases 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 230000001107 psychogenic effect Effects 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 150000003246 quinazolines Chemical class 0.000 description 1
- 108091008598 receptor tyrosine kinases Proteins 0.000 description 1
- 102000027426 receptor tyrosine kinases Human genes 0.000 description 1
- 230000000306 recurrent effect Effects 0.000 description 1
- 239000011607 retinol Substances 0.000 description 1
- 229960003471 retinol Drugs 0.000 description 1
- 235000020944 retinol Nutrition 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 208000012672 seasonal affective disease Diseases 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 150000003346 selenoethers Chemical class 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 229940057910 shea butter Drugs 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 210000000130 stem cell Anatomy 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 229940041022 streptomycins Drugs 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 150000004763 sulfides Chemical class 0.000 description 1
- 229940072176 sulfonamides and trimethoprim antibacterials for systemic use Drugs 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- 229940040944 tetracyclines Drugs 0.000 description 1
- 208000016595 therapy related acute myeloid leukemia and myelodysplastic syndrome Diseases 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 150000003595 thromboxanes Chemical class 0.000 description 1
- GZNAASVAJNXPPW-UHFFFAOYSA-M tin(4+) chloride dihydrate Chemical compound O.O.[Cl-].[Sn+4] GZNAASVAJNXPPW-UHFFFAOYSA-M 0.000 description 1
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Substances O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/48—Nitrogen atoms not forming part of a nitro radical
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/04—Antipruritics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
- A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Dermatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Neurology (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Transplantation (AREA)
- Surgery (AREA)
- Neurosurgery (AREA)
- Ophthalmology & Optometry (AREA)
- Pain & Pain Management (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Urology & Nephrology (AREA)
- Pulmonology (AREA)
- Biomedical Technology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicinal Preparation (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51321403P | 2003-10-23 | 2003-10-23 | |
| US60/513,214 | 2003-10-23 | ||
| PCT/IB2004/003698 WO2005040139A2 (en) | 2003-10-23 | 2004-10-22 | 2-aminoaryloxazole compounds as tyrosine kinase inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2004283162A1 AU2004283162A1 (en) | 2005-05-06 |
| AU2004283162B2 true AU2004283162B2 (en) | 2011-12-15 |
Family
ID=42827352
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2004283162A Ceased AU2004283162B2 (en) | 2003-10-23 | 2004-10-22 | 2-aminoaryloxazole compounds as tyrosine kinase inhibitors |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US7718676B2 (enExample) |
| EP (1) | EP1684750B1 (enExample) |
| JP (1) | JP4971797B2 (enExample) |
| CN (1) | CN1950347B (enExample) |
| AT (1) | ATE465731T1 (enExample) |
| AU (1) | AU2004283162B2 (enExample) |
| BR (1) | BRPI0415467A (enExample) |
| CA (1) | CA2542909C (enExample) |
| DK (1) | DK1684750T3 (enExample) |
| HR (1) | HRP20100326T1 (enExample) |
| IL (1) | IL175028A (enExample) |
| NO (1) | NO20062308L (enExample) |
| NZ (1) | NZ546645A (enExample) |
| PL (1) | PL1684750T3 (enExample) |
| WO (1) | WO2005040139A2 (enExample) |
Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3272995B1 (en) | 2003-05-31 | 2019-11-27 | OneSubsea IP UK Limited | Apparatus and method for recovering fluids from a well and/or injecting fluids into a well |
| WO2005000298A2 (en) * | 2003-06-03 | 2005-01-06 | Novartis Ag | 5-membered heterocycle-based p-38 inhibitors |
| CA2542909C (en) * | 2003-10-23 | 2012-07-10 | Ab Science | 2-aminoaryloxazole compounds as tyrosine kinase inhibitors |
| CA2555403C (en) | 2004-02-26 | 2012-08-21 | Des Enhanced Recovery Limited | Connection system for subsea flow interface equipment |
| WO2005102318A1 (en) * | 2004-04-20 | 2005-11-03 | Ab Science | Use of c-kit inhibitors for treating hiv related diseases |
| US20080146585A1 (en) * | 2004-04-20 | 2008-06-19 | Ab Science | Use Of C-Kit Inhibitors For Treating Inflammatory Muscle Disorders Including Myositis And Muscular Dystrophy |
| JP2007538064A (ja) * | 2004-05-18 | 2007-12-27 | アブ サイエンス | 化学または生物兵器に曝露された患者を処置するための肥満細胞阻害剤の使用法 |
| WO2005115385A1 (en) * | 2004-05-24 | 2005-12-08 | Ab Science | Use of c-kit inhibitors for treating acne |
| CA2603826C (en) * | 2005-04-04 | 2013-03-12 | Ab Science | Substituted oxazole derivatives and their use as tyrosine kinase inhibitors |
| US20060281788A1 (en) | 2005-06-10 | 2006-12-14 | Baumann Christian A | Synergistic modulation of flt3 kinase using a flt3 inhibitor and a farnesyl transferase inhibitor |
| EP1904065A2 (en) * | 2005-07-14 | 2008-04-02 | AB Science | Use of dual c-kit/fgfr3 inhibitors for treating multiple myeloma |
| WO2007076460A2 (en) * | 2005-12-23 | 2007-07-05 | Kalypsys, Inc. | Substituted thiazole ureas useful as inhibitors of protein kinases |
| US8697716B2 (en) | 2006-04-20 | 2014-04-15 | Janssen Pharmaceutica Nv | Method of inhibiting C-KIT kinase |
| ES2458291T3 (es) * | 2006-04-20 | 2014-04-30 | Janssen Pharmaceutica Nv | Derivados de amidas aromáticas como inhibidores de la cinasa C-KIT |
| KR101367645B1 (ko) | 2006-04-20 | 2014-02-27 | 얀센 파마슈티카 엔.브이. | Ｃ-ｆｍｓ 키나제의 저해제로서의 복소환식 화합물 |
| KR101367646B1 (ko) | 2006-04-20 | 2014-02-27 | 얀센 파마슈티카 엔.브이. | Ｃ-ｆｍｓ 키나제의 저해제 |
| GB0618001D0 (en) | 2006-09-13 | 2006-10-18 | Des Enhanced Recovery Ltd | Method |
| US7790756B2 (en) * | 2006-10-11 | 2010-09-07 | Deciphera Pharmaceuticals, Llc | Kinase inhibitors useful for the treatment of myleoproliferative diseases and other proliferative diseases |
| GB0625526D0 (en) | 2006-12-18 | 2007-01-31 | Des Enhanced Recovery Ltd | Apparatus and method |
| GB0625191D0 (en) | 2006-12-18 | 2007-01-24 | Des Enhanced Recovery Ltd | Apparatus and method |
| JP2010515708A (ja) * | 2007-01-12 | 2010-05-13 | アブ サイエンス | 代謝拮抗薬およびチロシンキナーゼ阻害剤を用いた固形癌の併用治療 |
| GB0701426D0 (en) * | 2007-01-25 | 2007-03-07 | Univ Sheffield | Compounds and their use |
| GB0709031D0 (en) | 2007-05-10 | 2007-06-20 | Sareum Ltd | Pharmaceutical compounds |
| JO3240B1 (ar) | 2007-10-17 | 2018-03-08 | Janssen Pharmaceutica Nv | c-fms مثبطات كيناز |
| FR2928150A1 (fr) * | 2008-02-29 | 2009-09-04 | Vetoquinol Sa Sa | Nouveaux derives 7-substitues de 3-carboxy-oxadiazino-quinolones, leur preparation et leur application comme anti-bacteriens |
| EP2145891A1 (en) * | 2008-07-09 | 2010-01-20 | Vetoquinol S.A. | 9-substituted-5-carboxy-oxadiazino-quinolone derivatives, their preparation and their application as anti-bacterials |
| GB0820819D0 (en) | 2008-11-13 | 2008-12-24 | Sareum Ltd | Pharmaceutical compounds |
| AU2010343102B2 (en) | 2009-12-29 | 2016-03-24 | Dana-Farber Cancer Institute, Inc. | Type II Raf kinase inhibitors |
| JP5580492B2 (ja) * | 2011-03-01 | 2014-08-27 | エヌファルマコン，エルエルシー | Ｎ−（４−メトキシフェニル）−１−フェニル−１ｈ−ピラゾール−３−アミンおよび関連化合物の使用 |
| US8551992B2 (en) | 2011-05-27 | 2013-10-08 | Neosome Life Sciences, LLC | Aminooxazole inhibitors of cyclin dependent kinases |
| CA2840029C (en) * | 2011-07-27 | 2021-07-20 | Ab Science | Oxazole and thiazole derivatives as selective protein kinase inhibitors (c-kit) |
| GB201202027D0 (en) | 2012-02-06 | 2012-03-21 | Sareum Ltd | Pharmaceutical compounds |
| PL2634185T3 (pl) | 2012-03-02 | 2016-06-30 | Sareum Ltd | Inhibitory kinazy TYK2 |
| JOP20180012A1 (ar) | 2012-08-07 | 2019-01-30 | Janssen Pharmaceutica Nv | عملية السلفنة باستخدام نونافلوروبوتانيسولفونيل فلوريد |
| US9303046B2 (en) | 2012-08-07 | 2016-04-05 | Janssen Pharmaceutica Nv | Process for the preparation of heterocyclic ester derivatives |
| US20160175302A1 (en) * | 2014-12-17 | 2016-06-23 | Ab Science | Masitinib for treating gastric cancer |
| CA2972239A1 (en) | 2014-12-23 | 2016-06-30 | Dana-Farber Cancer Institute, Inc. | Inhibitors of cyclin-dependent kinase 7 (cdk7) |
| ES2796276T3 (es) * | 2015-02-05 | 2020-11-26 | Ab Science | Compuestos con actividad antitumoral |
| CN107427521B (zh) | 2015-03-27 | 2021-08-03 | 达纳-法伯癌症研究所股份有限公司 | 细胞周期蛋白依赖性激酶的抑制剂 |
| EP4019515A1 (en) | 2015-09-09 | 2022-06-29 | Dana-Farber Cancer Institute, Inc. | Inhibitors of cyclin-dependent kinases |
| GB201617871D0 (en) | 2016-10-21 | 2016-12-07 | Sareum Limited | Pharmaceutical compounds |
| JP7590185B2 (ja) | 2018-06-25 | 2024-11-26 | ダナ－ファーバー キャンサー インスティテュート， インコーポレイテッド | Ｔａｉｒｅファミリーキナーゼインヒビターおよびそれらの使用 |
| GB201816369D0 (en) | 2018-10-08 | 2018-11-28 | Sareum Ltd | Pharmaceutical compounds |
| CN112480101B (zh) * | 2019-09-12 | 2022-11-25 | 中国科学院上海药物研究所 | 一类irak4激酶抑制剂及其制备和应用 |
| WO2022040558A1 (en) * | 2020-08-21 | 2022-02-24 | Pylon Manufacturing Corp. | Windshield wiper blade |
| CN113185511B (zh) * | 2021-05-24 | 2022-04-26 | 中国医学科学院医药生物技术研究所 | 一种嘧啶类化合物及其制备方法和应用 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5000775A (en) * | 1985-12-31 | 1991-03-19 | Monsanto Company | 2-amino-4,5-disubstituted-oxazole/thiazole compounds as herbicide antidotes |
| EP0949242A1 (en) * | 1996-12-24 | 1999-10-13 | Chugai Seiyaku Kabushiki Kaisha | Aromatic amine derivatives having nos inhibitory effect |
| US6596747B2 (en) * | 1998-10-29 | 2003-07-22 | Bristol-Myers Squibb Company | Compounds derived from an amine nucleus and pharmaceutical compositions comprising same |
Family Cites Families (59)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3740420A (en) | 1967-11-28 | 1973-06-19 | Crown Zellerbach Corp | Pharmaceutical compositions with dimethyl sulfoxide |
| FR2077803B1 (enExample) | 1970-02-16 | 1973-03-16 | Innothera Lab Sa | |
| US3743727A (en) | 1970-11-16 | 1973-07-03 | Crown Zellerbach Corp | Enhancing tissue penetration of certain antimicrobial agents with dimethyl sulfoxide |
| US4405616A (en) | 1975-06-19 | 1983-09-20 | Nelson Research & Development Company | Penetration enhancers for transdermal drug delivery of systemic agents |
| US3989816A (en) | 1975-06-19 | 1976-11-02 | Nelson Research & Development Company | Vehicle composition containing 1-substituted azacycloheptan-2-ones |
| US4343940A (en) | 1979-02-13 | 1982-08-10 | Mead Johnson & Company | Anti-tumor quinazoline compounds |
| CA1163561A (en) | 1979-11-06 | 1984-03-13 | Cyril Boroda | Preparation containing nitroglycerine and optionally other medicaments and preparation thereof |
| US4460372A (en) | 1981-02-17 | 1984-07-17 | Alza Corporation | Percutaneous absorption enhancer dispenser for use in coadministering drug and percutaneous absorption enhancer |
| US4379454A (en) | 1981-02-17 | 1983-04-12 | Alza Corporation | Dosage for coadministering drug and percutaneous absorption enhancer |
| US4411893A (en) | 1981-08-14 | 1983-10-25 | Minnesota Mining And Manufacturing Company | Topical medicament preparations |
| CA1236029A (en) | 1984-05-14 | 1988-05-03 | Edmund Sandborn | Pharmaceutical solutions comprising dimethyl sulfoxide |
| US4615699A (en) | 1985-05-03 | 1986-10-07 | Alza Corporation | Transdermal delivery system for delivering nitroglycerin at high transdermal fluxes |
| JPH0651679B2 (ja) * | 1986-07-21 | 1994-07-06 | 株式会社大塚製薬工場 | ｐ−アミノフェノ−ル誘導体 |
| US4868183A (en) * | 1986-07-21 | 1989-09-19 | Otsuka Pharmaceutical Factory, Inc. | N-pyrazinyl substituted P-aminophenols |
| US5217999A (en) | 1987-12-24 | 1993-06-08 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Styryl compounds which inhibit EGF receptor protein tyrosine kinase |
| DE3815221C2 (de) | 1988-05-04 | 1995-06-29 | Gradinger F Hermes Pharma | Verwendung einer Retinol- und/oder Retinsäureester enthaltenden pharmazeutischen Zubereitung zur Inhalation zur Einwirkung auf die Schleimhäute des Tracheo-Bronchialtraktes einschließlich der Lungenalveolen |
| ES2064101T3 (es) | 1990-04-02 | 1995-01-16 | Pfizer | Compuestos de acido bencilfosfonico inhibidores de la quinasa de tirosina. |
| US5302606A (en) | 1990-04-16 | 1994-04-12 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Styryl-substituted pyridyl compounds which inhibit EGF receptor tyrosine kinase |
| WO1992020642A1 (en) | 1991-05-10 | 1992-11-26 | Rhone-Poulenc Rorer International (Holdings) Inc. | Bis mono-and bicyclic aryl and heteroaryl compounds which inhibit egf and/or pdgf receptor tyrosine kinase |
| US5721237A (en) | 1991-05-10 | 1998-02-24 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Protein tyrosine kinase aryl and heteroaryl quinazoline compounds having selective inhibition of HER-2 autophosphorylation properties |
| US5710158A (en) | 1991-05-10 | 1998-01-20 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Aryl and heteroaryl quinazoline compounds which inhibit EGF and/or PDGF receptor tyrosine kinase |
| US5714493A (en) | 1991-05-10 | 1998-02-03 | Rhone-Poulenc Rorer Pharmaceuticals, Inc. | Aryl and heteroaryl quinazoline compounds which inhibit CSF-1R receptor tyrosine kinase |
| JPH06503095A (ja) | 1991-05-29 | 1994-04-07 | ファイザー・インコーポレーテッド | 三環式ポリヒドロキシ系のチロシンキナーゼ阻害薬 |
| US5213453A (en) | 1991-06-28 | 1993-05-25 | Tapmatic Corporation | Cooling systems in tapping attachments suitable for high pressure applications |
| GB9121418D0 (en) * | 1991-10-09 | 1991-11-20 | Nader Esfahani Rahim | Imaginograph |
| US5521184A (en) | 1992-04-03 | 1996-05-28 | Ciba-Geigy Corporation | Pyrimidine derivatives and processes for the preparation thereof |
| JPH08503450A (ja) | 1992-08-06 | 1996-04-16 | ワーナー−ランバート・コンパニー | 蛋白チロシンキナーゼを阻害し、かつ抗腫瘍特性を有する２−チオインドール（セレノインドール）および関連ジスルフィド（セレニド） |
| US5330992A (en) | 1992-10-23 | 1994-07-19 | Sterling Winthrop Inc. | 1-cyclopropyl-4-pyridyl-quinolinones |
| GB9323290D0 (en) | 1992-12-10 | 1994-01-05 | Zeneca Ltd | Quinazoline derivatives |
| GB9226855D0 (en) | 1992-12-23 | 1993-02-17 | Erba Carlo Spa | Vinylene-azaindole derivatives and process for their preparation |
| US5656643A (en) | 1993-11-08 | 1997-08-12 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Bis mono-and bicyclic aryl and heteroaryl compounds which inhibit EGF and/or PDGF receptor tyrosine kinase |
| US5880141A (en) | 1995-06-07 | 1999-03-09 | Sugen, Inc. | Benzylidene-Z-indoline compounds for the treatment of disease |
| US5906202A (en) | 1996-11-21 | 1999-05-25 | Aradigm Corporation | Device and method for directing aerosolized mist to a specific area of the respiratory tract |
| JPH10237028A (ja) * | 1996-12-24 | 1998-09-08 | Chugai Pharmaceut Co Ltd | Ｎｏｓ阻害作用を有する芳香族アミン誘導体 |
| CO4940418A1 (es) | 1997-07-18 | 2000-07-24 | Novartis Ag | Modificacion de cristal de un derivado de n-fenil-2- pirimidinamina, procesos para su fabricacion y su uso |
| JP2002528499A (ja) * | 1998-10-29 | 2002-09-03 | ブリストル−マイヤーズ スクイブ カンパニー | Ｉｍｐｄｈ酵素のインヒビターであるアミノ核誘導化合物 |
| MXPA01006742A (es) | 1998-12-31 | 2004-04-21 | Sugen Inc | Compuestos 3-heteroarilidenil-2-indolinona para modular la actividad de la quinasa de proteina y para utilizarse en la quimioterapia de cancer. |
| US20020137755A1 (en) | 2000-12-04 | 2002-09-26 | Bilodeau Mark T. | Tyrosine kinase inhibitors |
| US20030091974A1 (en) | 2001-06-29 | 2003-05-15 | Alain Moussy | Method for screening compounds capable of depleting mast cells |
| ES2266553T3 (es) | 2001-06-29 | 2007-03-01 | Ab Science | Utilizacion de derivados de la n-fenil-2-pirimidina-amina para tratar las enfermedades inflamatorias. |
| US7727731B2 (en) | 2001-06-29 | 2010-06-01 | Ab Science | Potent, selective and non toxic c-kit inhibitors |
| EP1401414A2 (en) | 2001-06-29 | 2004-03-31 | AB Science | Use of tyrosine kinase inhibitors for treating multiple sclerosis (ms) |
| US20050054617A1 (en) | 2001-06-29 | 2005-03-10 | Alain Moussy | Use of potent, selective and non toxic c-kit inhibitors for treating mastocytosis |
| WO2003004006A2 (en) | 2001-06-29 | 2003-01-16 | Ab Science | Use of potent, selective and non toxic c-kit inhibitors for treating tumor angiogenesis |
| CA2452390A1 (en) | 2001-06-29 | 2003-01-09 | Ab Science | Use of tyrosine kinase inhibitors for treating bone loss |
| US7700610B2 (en) | 2001-06-29 | 2010-04-20 | Ab Science | Use of tyrosine kinase inhibitors for treating allergic diseases |
| CA2452361A1 (en) | 2001-06-29 | 2003-01-09 | Ab Science | Use of tyrosine kinase inhibitors for treating autoimmune diseases |
| ES2274075T3 (es) | 2001-06-29 | 2007-05-16 | Ab Science | Utilizacion de inhibidores de c-kit para tratar enfermedades inflamatorias intestinales (eii). |
| JP2005507916A (ja) | 2001-09-20 | 2005-03-24 | アブ サイエンス | 細菌感染症を治療するための、強力で選択的かつ非毒性のｃ−ｋｉｔ阻害剤の使用方法 |
| WO2003039550A1 (en) | 2001-09-20 | 2003-05-15 | Ab Science | Use of tyrosine kinase inhibitors for whitening human skin and treating melanocyte dysfunction associated diseases |
| US20040242612A1 (en) | 2001-09-20 | 2004-12-02 | Alain Moussy | Use of tyrosine kinase inhibitors for promoting hair growth |
| DE60323613D1 (de) | 2002-02-27 | 2008-10-30 | Ab Science | Verwendung von tyrosinkinase-hemmern zur behandlung von erkrankungen im zusammenhang mit substanzgebrauch |
| WO2003072090A2 (en) | 2002-02-27 | 2003-09-04 | Ab Science | Use of tyrosine kinase inhibitors for treating cns disorders |
| TW200401638A (en) * | 2002-06-20 | 2004-02-01 | Bristol Myers Squibb Co | Heterocyclic inhibitors of kinases |
| JP2006503081A (ja) * | 2002-10-10 | 2006-01-26 | スミスクライン ビーチャム コーポレーション | 化学化合物 |
| EP1597398B1 (en) | 2003-02-27 | 2008-04-23 | AB Science | Method of diagnostic of mastocytosis |
| WO2005000298A2 (en) * | 2003-06-03 | 2005-01-06 | Novartis Ag | 5-membered heterocycle-based p-38 inhibitors |
| CN1829513A (zh) * | 2003-06-03 | 2006-09-06 | 诺瓦提斯公司 | 基于五元杂环的p－38抑制剂 |
| CA2542909C (en) | 2003-10-23 | 2012-07-10 | Ab Science | 2-aminoaryloxazole compounds as tyrosine kinase inhibitors |
-
2004
- 2004-10-22 CA CA2542909A patent/CA2542909C/en not_active Expired - Fee Related
- 2004-10-22 AT AT04791783T patent/ATE465731T1/de active
- 2004-10-22 BR BRPI0415467-3A patent/BRPI0415467A/pt not_active IP Right Cessation
- 2004-10-22 CN CN2004800371595A patent/CN1950347B/zh not_active Expired - Fee Related
- 2004-10-22 EP EP04791783A patent/EP1684750B1/en not_active Expired - Lifetime
- 2004-10-22 NZ NZ546645A patent/NZ546645A/en not_active IP Right Cessation
- 2004-10-22 PL PL04791783T patent/PL1684750T3/pl unknown
- 2004-10-22 JP JP2006536215A patent/JP4971797B2/ja not_active Expired - Fee Related
- 2004-10-22 WO PCT/IB2004/003698 patent/WO2005040139A2/en not_active Ceased
- 2004-10-22 HR HR20100326T patent/HRP20100326T1/hr unknown
- 2004-10-22 AU AU2004283162A patent/AU2004283162B2/en not_active Ceased
- 2004-10-22 DK DK04791783.6T patent/DK1684750T3/da active
- 2004-10-22 US US10/576,267 patent/US7718676B2/en not_active Expired - Fee Related
-
2006
- 2006-04-20 IL IL175028A patent/IL175028A/en not_active IP Right Cessation
- 2006-05-22 NO NO20062308A patent/NO20062308L/no not_active Application Discontinuation
-
2010
- 2010-01-11 US US12/654,957 patent/US8110591B2/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5000775A (en) * | 1985-12-31 | 1991-03-19 | Monsanto Company | 2-amino-4,5-disubstituted-oxazole/thiazole compounds as herbicide antidotes |
| EP0949242A1 (en) * | 1996-12-24 | 1999-10-13 | Chugai Seiyaku Kabushiki Kaisha | Aromatic amine derivatives having nos inhibitory effect |
| US6596747B2 (en) * | 1998-10-29 | 2003-07-22 | Bristol-Myers Squibb Company | Compounds derived from an amine nucleus and pharmaceutical compositions comprising same |
Non-Patent Citations (1)
| Title |
|---|
| Nath et al, 'Synthesis and mercuration of some new 2-arylamino-4,5-disubstituted oxazoles as pesticides', Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1981, Vol 20(B), pp 827-9 * |
Also Published As
| Publication number | Publication date |
|---|---|
| US8110591B2 (en) | 2012-02-07 |
| BRPI0415467A (pt) | 2006-12-19 |
| HRP20100326T1 (hr) | 2010-10-31 |
| WO2005040139A8 (en) | 2006-06-01 |
| CA2542909A1 (en) | 2005-05-06 |
| NO20062308L (no) | 2006-05-22 |
| AU2004283162A1 (en) | 2005-05-06 |
| DK1684750T3 (da) | 2010-08-09 |
| EP1684750A2 (en) | 2006-08-02 |
| JP2007509130A (ja) | 2007-04-12 |
| HK1091134A1 (en) | 2007-01-12 |
| US20070142390A1 (en) | 2007-06-21 |
| IL175028A0 (en) | 2006-08-20 |
| NZ546645A (en) | 2010-02-26 |
| CN1950347B (zh) | 2012-04-04 |
| JP4971797B2 (ja) | 2012-07-11 |
| WO2005040139A2 (en) | 2005-05-06 |
| ATE465731T1 (de) | 2010-05-15 |
| CA2542909C (en) | 2012-07-10 |
| US7718676B2 (en) | 2010-05-18 |
| EP1684750B1 (en) | 2010-04-28 |
| CN1950347A (zh) | 2007-04-18 |
| WO2005040139A3 (en) | 2005-10-13 |
| IL175028A (en) | 2011-02-28 |
| US20100113471A1 (en) | 2010-05-06 |
| PL1684750T3 (pl) | 2010-10-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU2004283162B2 (en) | 2-aminoaryloxazole compounds as tyrosine kinase inhibitors | |
| US8658659B2 (en) | Substituted oxazole derivatives and their use as tyrosine kinase inhibitors | |
| US8835435B2 (en) | 2-(3-aminoaryl) amino-4-aryl-thiazoles and their use as c-kit inhibitors | |
| AU2005209485A1 (en) | 2-(3-substituted-aryl)amino-4-aryl-thiazoles as tyrosine kinase inhibitors | |
| KR101164754B1 (ko) | 티로신 키나제 억제제로서의 2-아미노아릴옥사졸 화합물 | |
| WO2006064375A9 (en) | Aminoaryl substituted five-membered ring heterocyclic compounds for the treatment of diseases | |
| WO2007065939A1 (en) | Substituted thiazole derivatives and their uses as tyrosine kinase inhibitors | |
| US20080039466A1 (en) | 2-(3-Substituted-Aryl) Amino-4-Aryl-Thiazoles As Tyrosine Kinase Inhibitors | |
| HK1091134B (en) | 2-aminoaryloxazole compounds as tyrosine kinase inhibitors | |
| MXPA06004581A (en) | 2-aminoaryloxazole compounds as tyrosine kinase inhibitors | |
| HK1112195B (en) | Substituted oxazole derivatives and their use as tyrosine kinase inhibitors | |
| MXPA06008597A (en) | 2-(3-substituted-aryl)amino-4-aryl-thiazoles as tyrosine kinase inhibitors |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |