JP2008525502A - 抗炎症薬 - Google Patents
抗炎症薬 Download PDFInfo
- Publication number
- JP2008525502A JP2008525502A JP2007548611A JP2007548611A JP2008525502A JP 2008525502 A JP2008525502 A JP 2008525502A JP 2007548611 A JP2007548611 A JP 2007548611A JP 2007548611 A JP2007548611 A JP 2007548611A JP 2008525502 A JP2008525502 A JP 2008525502A
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- pyrazol
- urea
- dichlorophenyl
- oxoethyl
- 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.)
- Abandoned
Links
- 239000002260 anti-inflammatory agent Substances 0.000 title 1
- 229940124599 anti-inflammatory drug Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 114
- 238000000034 method Methods 0.000 claims abstract description 68
- 108091000080 Phosphotransferase Proteins 0.000 claims abstract description 24
- 102000020233 phosphotransferase Human genes 0.000 claims abstract description 24
- 201000010099 disease Diseases 0.000 claims abstract description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 11
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 4
- 201000011510 cancer Diseases 0.000 claims abstract description 4
- 230000003463 hyperproliferative effect Effects 0.000 claims abstract description 4
- WEVYNIUIFUYDGI-UHFFFAOYSA-N 3-[6-[4-(trifluoromethoxy)anilino]-4-pyrimidinyl]benzamide Chemical compound NC(=O)C1=CC=CC(C=2N=CN=C(NC=3C=CC(OC(F)(F)F)=CC=3)C=2)=C1 WEVYNIUIFUYDGI-UHFFFAOYSA-N 0.000 claims abstract 2
- 230000004913 activation Effects 0.000 claims abstract 2
- -1 β-trimethylsilylethyl Chemical group 0.000 claims description 97
- 125000000217 alkyl group Chemical group 0.000 claims description 38
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 34
- 125000003118 aryl group Chemical group 0.000 claims description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 24
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 23
- 125000000623 heterocyclic group Chemical group 0.000 claims description 22
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 21
- 239000004202 carbamide Substances 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 11
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 125000002883 imidazolyl group Chemical group 0.000 claims description 9
- 125000002971 oxazolyl group Chemical group 0.000 claims description 9
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 9
- 125000001544 thienyl group Chemical group 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 125000001769 aryl amino group Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 8
- 125000002541 furyl group Chemical group 0.000 claims description 7
- 208000027866 inflammatory disease Diseases 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 7
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 7
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 7
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 7
- 125000000335 thiazolyl group Chemical group 0.000 claims description 7
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
- 125000004193 piperazinyl group Chemical group 0.000 claims description 6
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 5
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 5
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 5
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 5
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 5
- 125000004043 oxo group Chemical group O=* 0.000 claims description 5
- 125000003386 piperidinyl group Chemical group 0.000 claims description 5
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000005110 aryl thio group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 4
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 4
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000005044 dihydroquinolinyl group Chemical group N1(CC=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 3
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 3
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000005545 phthalimidyl group Chemical group 0.000 claims description 3
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 3
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
- 125000004306 triazinyl group Chemical group 0.000 claims description 3
- 125000001425 triazolyl group Chemical group 0.000 claims description 3
- RXKFJNZGJZMMND-UHFFFAOYSA-N 1-(2,3-dichlorophenyl)-3-[2-[3-(hydroxymethyl)phenyl]-5-phenylpyrazol-3-yl]urea Chemical compound OCC1=CC=CC(N2C(=CC(=N2)C=2C=CC=CC=2)NC(=O)NC=2C(=C(Cl)C=CC=2)Cl)=C1 RXKFJNZGJZMMND-UHFFFAOYSA-N 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 125000002723 alicyclic group Chemical group 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 2
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000002785 azepinyl group Chemical group 0.000 claims description 2
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 2
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 230000002452 interceptive effect Effects 0.000 claims description 2
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000003566 oxetanyl group Chemical group 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 2
- 206010040070 Septic Shock Diseases 0.000 claims 9
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 6
- 108060006633 protein kinase Proteins 0.000 claims 4
- 208000024891 symptom Diseases 0.000 claims 4
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 3
- 206010009900 Colitis ulcerative Diseases 0.000 claims 3
- 208000011231 Crohn disease Diseases 0.000 claims 3
- 201000005569 Gout Diseases 0.000 claims 3
- 206010018634 Gouty Arthritis Diseases 0.000 claims 3
- 206010061218 Inflammation Diseases 0.000 claims 3
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 3
- 102000001253 Protein Kinase Human genes 0.000 claims 3
- 201000004681 Psoriasis Diseases 0.000 claims 3
- 206010063837 Reperfusion injury Diseases 0.000 claims 3
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 3
- 206010040047 Sepsis Diseases 0.000 claims 3
- 208000006011 Stroke Diseases 0.000 claims 3
- 206010044248 Toxic shock syndrome Diseases 0.000 claims 3
- 231100000650 Toxic shock syndrome Toxicity 0.000 claims 3
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 3
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims 3
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 3
- 208000006673 asthma Diseases 0.000 claims 3
- 201000005008 bacterial sepsis Diseases 0.000 claims 3
- 208000019664 bone resorption disease Diseases 0.000 claims 3
- 230000001684 chronic effect Effects 0.000 claims 3
- 208000024908 graft versus host disease Diseases 0.000 claims 3
- 230000004054 inflammatory process Effects 0.000 claims 3
- 208000014674 injury Diseases 0.000 claims 3
- 208000028867 ischemia Diseases 0.000 claims 3
- 230000001537 neural effect Effects 0.000 claims 3
- 230000000926 neurological effect Effects 0.000 claims 3
- 201000008482 osteoarthritis Diseases 0.000 claims 3
- 230000002685 pulmonary effect Effects 0.000 claims 3
- 208000037803 restenosis Diseases 0.000 claims 3
- 230000036303 septic shock Effects 0.000 claims 3
- 230000008733 trauma Effects 0.000 claims 3
- VNNSYZVMRNOQML-HXUWFJFHSA-N 1-[5-tert-butyl-2-[4-[2-[(3r)-3-(dimethylamino)pyrrolidin-1-yl]-2-oxoethyl]phenyl]pyrazol-3-yl]-3-(2,3-dichlorophenyl)urea Chemical compound C1[C@H](N(C)C)CCN1C(=O)CC1=CC=C(N2C(=CC(=N2)C(C)(C)C)NC(=O)NC=2C(=C(Cl)C=CC=2)Cl)C=C1 VNNSYZVMRNOQML-HXUWFJFHSA-N 0.000 claims 2
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims 2
- 125000003310 benzodiazepinyl group Chemical group N1N=C(C=CC2=C1C=CC=C2)* 0.000 claims 2
- 125000005045 dihydroisoquinolinyl group Chemical group C1(NC=CC2=CC=CC=C12)* 0.000 claims 2
- 108020001507 fusion proteins Proteins 0.000 claims 2
- 102000037865 fusion proteins Human genes 0.000 claims 2
- 208000002780 macular degeneration Diseases 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- XJLSEXAGTJCILF-RXMQYKEDSA-N (R)-nipecotic acid zwitterion Chemical compound OC(=O)[C@@H]1CCCNC1 XJLSEXAGTJCILF-RXMQYKEDSA-N 0.000 claims 1
- MEKVKUUTWATHTN-SFHVURJKSA-N 1-(2,3-dichlorophenyl)-3-[2-[3-[2-[(3s)-3-hydroxypyrrolidin-1-yl]-2-oxoethyl]phenyl]-5-thiophen-2-ylpyrazol-3-yl]urea Chemical compound C1[C@@H](O)CCN1C(=O)CC1=CC=CC(N2C(=CC(=N2)C=2SC=CC=2)NC(=O)NC=2C(=C(Cl)C=CC=2)Cl)=C1 MEKVKUUTWATHTN-SFHVURJKSA-N 0.000 claims 1
- TVYRLXMVKIOKKW-UHFFFAOYSA-N 1-(2,3-dichlorophenyl)-3-[5-(2-fluorophenyl)-2-[3-(hydroxymethyl)phenyl]pyrazol-3-yl]urea Chemical compound OCC1=CC=CC(N2C(=CC(=N2)C=2C(=CC=CC=2)F)NC(=O)NC=2C(=C(Cl)C=CC=2)Cl)=C1 TVYRLXMVKIOKKW-UHFFFAOYSA-N 0.000 claims 1
- ZSGXAQVTUCIJQL-IBGZPJMESA-N 1-(2,3-dichlorophenyl)-3-[5-(2-fluorophenyl)-2-[4-[2-[(3s)-3-hydroxypyrrolidin-1-yl]-2-oxoethyl]phenyl]pyrazol-3-yl]urea Chemical compound C1[C@@H](O)CCN1C(=O)CC1=CC=C(N2C(=CC(=N2)C=2C(=CC=CC=2)F)NC(=O)NC=2C(=C(Cl)C=CC=2)Cl)C=C1 ZSGXAQVTUCIJQL-IBGZPJMESA-N 0.000 claims 1
- OVPPOGWZSQYJDZ-UHFFFAOYSA-N 2-[3-[3-cyclopentyl-5-[(2,3-dichlorophenyl)carbamoylamino]pyrazol-1-yl]phenyl]-n-(2,3-dihydroxypropyl)acetamide Chemical compound OCC(O)CNC(=O)CC1=CC=CC(N2C(=CC(=N2)C2CCCC2)NC(=O)NC=2C(=C(Cl)C=CC=2)Cl)=C1 OVPPOGWZSQYJDZ-UHFFFAOYSA-N 0.000 claims 1
- WVTCZWKFBQRSJH-UHFFFAOYSA-N 2-[3-[3-cyclopentyl-5-[(2,3-dichlorophenyl)carbamoylamino]pyrazol-1-yl]phenyl]-n-(2-hydroxyethyl)acetamide Chemical compound OCCNC(=O)CC1=CC=CC(N2C(=CC(=N2)C2CCCC2)NC(=O)NC=2C(=C(Cl)C=CC=2)Cl)=C1 WVTCZWKFBQRSJH-UHFFFAOYSA-N 0.000 claims 1
- CDHWPDARBORLQH-UHFFFAOYSA-N 2-[3-[3-cyclopentyl-5-[(2,3-dichlorophenyl)carbamoylamino]pyrazol-1-yl]phenyl]acetamide Chemical compound NC(=O)CC1=CC=CC(N2C(=CC(=N2)C2CCCC2)NC(=O)NC=2C(=C(Cl)C=CC=2)Cl)=C1 CDHWPDARBORLQH-UHFFFAOYSA-N 0.000 claims 1
- MRLOXPNJVSEIRZ-UHFFFAOYSA-N 2-[3-[3-cyclopentyl-5-[(2,3-dichlorophenyl)carbamoylamino]pyrazol-1-yl]phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC(N2C(=CC(=N2)C2CCCC2)NC(=O)NC=2C(=C(Cl)C=CC=2)Cl)=C1 MRLOXPNJVSEIRZ-UHFFFAOYSA-N 0.000 claims 1
- FYBUDULPILUHEB-UHFFFAOYSA-N 2-[3-[3-cyclopentyl-5-[[3-(8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl)phenyl]carbamoylamino]pyrazol-1-yl]phenyl]acetamide Chemical compound O=C1N(C)C2=NC=NC=C2C=C1C(C=1)=CC=CC=1NC(=O)NC1=CC(C2CCCC2)=NN1C1=CC=CC(CC(N)=O)=C1 FYBUDULPILUHEB-UHFFFAOYSA-N 0.000 claims 1
- CFHMPQWTLXQQGE-UHFFFAOYSA-N 2-[3-[3-cyclopentyl-5-[[4-(1-oxo-2,3-dihydroisoindol-4-yl)phenyl]carbamoylamino]pyrazol-1-yl]phenyl]acetamide Chemical compound NC(=O)CC1=CC=CC(N2C(=CC(=N2)C2CCCC2)NC(=O)NC=2C=CC(=CC=2)C=2C=3CNC(=O)C=3C=CC=2)=C1 CFHMPQWTLXQQGE-UHFFFAOYSA-N 0.000 claims 1
- BRAKGANXHZKVQP-UHFFFAOYSA-N 2-[3-[3-phenyl-5-[(3-pyridin-3-yloxyphenyl)carbamoylamino]pyrazol-1-yl]phenyl]acetamide Chemical compound NC(=O)CC1=CC=CC(N2C(=CC(=N2)C=2C=CC=CC=2)NC(=O)NC=2C=C(OC=3C=NC=CC=3)C=CC=2)=C1 BRAKGANXHZKVQP-UHFFFAOYSA-N 0.000 claims 1
- ICNXRBASKDUBJL-UHFFFAOYSA-N 2-[3-[3-tert-butyl-5-[(2,3,4-trifluorophenyl)carbamoylamino]pyrazol-1-yl]phenyl]acetamide Chemical compound C=1C=CC(CC(N)=O)=CC=1N1N=C(C(C)(C)C)C=C1NC(=O)NC1=CC=C(F)C(F)=C1F ICNXRBASKDUBJL-UHFFFAOYSA-N 0.000 claims 1
- MMEYNYHTUVXSCU-UHFFFAOYSA-N 2-[3-[3-tert-butyl-5-[(3-pyridin-3-yloxyphenyl)carbamoylamino]pyrazol-1-yl]phenyl]acetamide Chemical compound C=1C=CC(CC(N)=O)=CC=1N1N=C(C(C)(C)C)C=C1NC(=O)NC(C=1)=CC=CC=1OC1=CC=CN=C1 MMEYNYHTUVXSCU-UHFFFAOYSA-N 0.000 claims 1
- JCNDKKIMAKONEI-UHFFFAOYSA-N 2-[3-[3-tert-butyl-5-[(3-pyridin-3-ylphenyl)carbamoylamino]pyrazol-1-yl]phenyl]acetamide Chemical compound C=1C=CC(CC(N)=O)=CC=1N1N=C(C(C)(C)C)C=C1NC(=O)NC(C=1)=CC=CC=1C1=CC=CN=C1 JCNDKKIMAKONEI-UHFFFAOYSA-N 0.000 claims 1
- AXDMTDUAXWCVPA-UHFFFAOYSA-N 2-[3-[3-tert-butyl-5-[(4-pyridin-4-yloxyphenyl)carbamoylamino]pyrazol-1-yl]phenyl]acetamide Chemical compound C=1C=CC(CC(N)=O)=CC=1N1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=NC=C1 AXDMTDUAXWCVPA-UHFFFAOYSA-N 0.000 claims 1
- SIRQROHWTHZOSI-UHFFFAOYSA-N 2-[3-[3-tert-butyl-5-[[4-methyl-3-(pyrimidin-2-ylamino)phenyl]carbamoylamino]pyrazol-1-yl]phenyl]acetamide Chemical compound C1=C(NC=2N=CC=CN=2)C(C)=CC=C1NC(=O)NC1=CC(C(C)(C)C)=NN1C1=CC=CC(CC(N)=O)=C1 SIRQROHWTHZOSI-UHFFFAOYSA-N 0.000 claims 1
- KYSOKGJGZUNAFL-UHFFFAOYSA-N 2-[3-[3-tert-butyl-5-[[4-methyl-3-[(4-pyridin-3-ylpyrimidin-2-yl)amino]phenyl]carbamoylamino]pyrazol-1-yl]phenyl]acetamide Chemical compound C1=C(NC=2N=C(C=CN=2)C=2C=NC=CC=2)C(C)=CC=C1NC(=O)NC1=CC(C(C)(C)C)=NN1C1=CC=CC(CC(N)=O)=C1 KYSOKGJGZUNAFL-UHFFFAOYSA-N 0.000 claims 1
- VIMDVWLSWRBKRQ-UHFFFAOYSA-N 2-[3-[5-[(2,3-dichlorophenyl)carbamoylamino]-3-(2-fluorophenyl)pyrazol-1-yl]phenyl]-n-(1,3-dihydroxypropan-2-yl)acetamide Chemical compound OCC(CO)NC(=O)CC1=CC=CC(N2C(=CC(=N2)C=2C(=CC=CC=2)F)NC(=O)NC=2C(=C(Cl)C=CC=2)Cl)=C1 VIMDVWLSWRBKRQ-UHFFFAOYSA-N 0.000 claims 1
- OMVCJRIDEPKTJZ-UHFFFAOYSA-N 2-[3-[5-[(2,3-dichlorophenyl)carbamoylamino]-3-(2-fluorophenyl)pyrazol-1-yl]phenyl]-n-(2,3-dihydroxypropyl)acetamide Chemical compound OCC(O)CNC(=O)CC1=CC=CC(N2C(=CC(=N2)C=2C(=CC=CC=2)F)NC(=O)NC=2C(=C(Cl)C=CC=2)Cl)=C1 OMVCJRIDEPKTJZ-UHFFFAOYSA-N 0.000 claims 1
- SMPOYUSWIAZPRX-UHFFFAOYSA-N 2-[3-[5-[(2,3-dichlorophenyl)carbamoylamino]-3-(2-fluorophenyl)pyrazol-1-yl]phenyl]-n-(2-hydroxyethyl)acetamide Chemical compound OCCNC(=O)CC1=CC=CC(N2C(=CC(=N2)C=2C(=CC=CC=2)F)NC(=O)NC=2C(=C(Cl)C=CC=2)Cl)=C1 SMPOYUSWIAZPRX-UHFFFAOYSA-N 0.000 claims 1
- NWOGJAKKLLVTRV-UHFFFAOYSA-N 2-[3-[5-[(2,3-dichlorophenyl)carbamoylamino]-3-(2-fluorophenyl)pyrazol-1-yl]phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC(N2C(=CC(=N2)C=2C(=CC=CC=2)F)NC(=O)NC=2C(=C(Cl)C=CC=2)Cl)=C1 NWOGJAKKLLVTRV-UHFFFAOYSA-N 0.000 claims 1
- XRLOEXOWYIVSTJ-UHFFFAOYSA-N 2-[3-[5-[(2,3-dichlorophenyl)carbamoylamino]-3-(3-fluorophenyl)pyrazol-1-yl]phenyl]acetamide Chemical compound NC(=O)CC1=CC=CC(N2C(=CC(=N2)C=2C=C(F)C=CC=2)NC(=O)NC=2C(=C(Cl)C=CC=2)Cl)=C1 XRLOEXOWYIVSTJ-UHFFFAOYSA-N 0.000 claims 1
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- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
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Classifications
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US63898704P | 2004-12-23 | 2004-12-23 | |
| PCT/US2005/047597 WO2006081034A2 (en) | 2004-12-23 | 2005-12-23 | Anti-inflammatory medicaments |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008525502A true JP2008525502A (ja) | 2008-07-17 |
| JP2008525502A5 JP2008525502A5 (enExample) | 2009-01-29 |
Family
ID=36740941
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007548611A Abandoned JP2008525502A (ja) | 2004-12-23 | 2005-12-23 | 抗炎症薬 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20090312349A1 (enExample) |
| EP (1) | EP1836173A4 (enExample) |
| JP (1) | JP2008525502A (enExample) |
| AU (1) | AU2005325676A1 (enExample) |
| CA (1) | CA2592116A1 (enExample) |
| WO (1) | WO2006081034A2 (enExample) |
Families Citing this family (51)
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| US20070078121A1 (en) | 2004-12-23 | 2007-04-05 | Flynn Daniel L | Enzyme modulators and treatments |
| DE102006029795A1 (de) * | 2006-06-27 | 2008-01-03 | Schebo Biotech Ag | Neue Harnstoff-Derivate und deren Verwendungen |
| WO2008026704A1 (en) * | 2006-08-31 | 2008-03-06 | Kyowa Hakko Kogyo Co., Ltd. | Isoquinoline derivative |
| US7897762B2 (en) * | 2006-09-14 | 2011-03-01 | Deciphera Pharmaceuticals, Llc | Kinase inhibitors useful for the treatment of proliferative diseases |
| US8188113B2 (en) | 2006-09-14 | 2012-05-29 | Deciphera Pharmaceuticals, Inc. | Dihydropyridopyrimidinyl, dihydronaphthyidinyl and related compounds useful as kinase inhibitors for the treatment of proliferative diseases |
| US7790756B2 (en) | 2006-10-11 | 2010-09-07 | Deciphera Pharmaceuticals, Llc | Kinase inhibitors useful for the treatment of myleoproliferative diseases and other proliferative diseases |
| AU2007309279B2 (en) * | 2006-10-20 | 2011-03-24 | Irm Llc | Compositions and methods for modulating c-kit and PDGFR receptors |
| KR20120049397A (ko) * | 2006-11-03 | 2012-05-16 | 노파르티스 아게 | 단백질 키나제 억제제로서의 화합물 및 조성물 |
| EP2481736A1 (en) * | 2007-04-20 | 2012-08-01 | Deciphera Pharmaceuticals, LLC. | Kinase inhibitors useful for the treatment of myleoproliferative diseases and other proliferative diseases |
| US20110189167A1 (en) * | 2007-04-20 | 2011-08-04 | Flynn Daniel L | Methods and Compositions for the Treatment of Myeloproliferative Diseases and other Proliferative Diseases |
| EP2152688A1 (en) | 2007-05-04 | 2010-02-17 | Irm Llc | Compounds and compositions as c-kit and pdgfr kinase inhibitors |
| WO2009026204A1 (en) | 2007-08-22 | 2009-02-26 | Irm Llc | 2-heteroarylamino-pyrimidine derivatives as kinase inhibitors |
| MX2010002004A (es) | 2007-08-22 | 2010-03-11 | Irm Llc | Compuestos de 5-(4-(halo-alcoxi)-fenil)-pirimidin-2-amina y composiciones con inhibidores de cinasa. |
| BRPI0908849A2 (pt) * | 2008-02-22 | 2015-08-25 | Irm Llc | Composto e composições como c-kit e inibidores de pdgfr quinase |
| CN102186809A (zh) | 2008-08-14 | 2011-09-14 | 拜尔农作物科学股份公司 | 杀虫性的4-苯基-1h-吡唑 |
| BRPI0920707A2 (pt) | 2008-10-02 | 2015-12-29 | Respivert Ltd | compostos |
| GB0818033D0 (en) | 2008-10-02 | 2008-11-05 | Respivert Ltd | Novel compound |
| KR20110099687A (ko) * | 2008-10-29 | 2011-09-08 | 데시페라 파마슈티칼스, 엘엘씨. | 항-암과 항-증식성 활성을 나타내는 시클로프로판 아미드와 유사체 |
| EP2370428B1 (en) | 2008-12-11 | 2016-08-10 | Respivert Limited | P38 map kinase inhibitors |
| GB0905955D0 (en) | 2009-04-06 | 2009-05-20 | Respivert Ltd | Novel compounds |
| EP2686317A4 (en) * | 2011-03-17 | 2014-08-20 | Selexagen Therapeutics Inc | RAF KINASE INHIBITORS |
| SI2712358T1 (sl) | 2011-05-13 | 2017-03-31 | Array Biopharma, Inc. | Spojine pirolidinil sečnine, pirolidinil tiosečnine in pirolidinil gvanidina kot inhibitorji kinaze trka |
| JP2014521617A (ja) | 2011-07-26 | 2014-08-28 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | バニロイド受容体リガンドとしての置換二環性芳香族カルボキサミドおよび尿素誘導体 |
| GB201113538D0 (en) | 2011-08-04 | 2011-09-21 | Karobio Ab | Novel estrogen receptor ligands |
| US8461179B1 (en) | 2012-06-07 | 2013-06-11 | Deciphera Pharmaceuticals, Llc | Dihydronaphthyridines and related compounds useful as kinase inhibitors for the treatment of proliferative diseases |
| WO2014078331A1 (en) | 2012-11-13 | 2014-05-22 | Array Biopharma Inc. | N-(arylalkyl)-n'-pyrazolyl-urea, thiourea, guanidine and cyanoguanidine compounds as trka kinase inhibitors |
| WO2014078328A1 (en) | 2012-11-13 | 2014-05-22 | Array Biopharma Inc. | N-bicyclic aryl,n'-pyrazolyl urea, thiourea, guanidine and cyanoguanidine compounds as trka kinase inhibitors |
| ES2664331T3 (es) | 2012-11-13 | 2018-04-19 | Array Biopharma, Inc. | Compuestos de N-pirrolidinilo, N'-pirazolilurea, tiourea, guanidina y cianoguanidina como inhibidores de la cinasa Trka |
| US9809578B2 (en) | 2012-11-13 | 2017-11-07 | Array Biopharma Inc. | Pyrazolyl urea, thiourea, guanidine and cyanoguanidine compounds as trkA kinase inhibitors |
| RU2664541C2 (ru) | 2012-11-13 | 2018-08-20 | Эррэй Биофарма Инк. | Бициклические соединения мочевины, тиомочевины, гуанидина и цианогуанидина, пригодные для лечения боли |
| WO2014078325A1 (en) | 2012-11-13 | 2014-05-22 | Array Biopharma Inc. | N-(monocyclic aryl),n'-pyrazolyl-urea, thiourea, guanidine and cyanoguanidine compounds as trka kinase inhibitors |
| US9828360B2 (en) | 2012-11-13 | 2017-11-28 | Array Biopharma Inc. | Pyrrolidinyl urea, thiourea, guanidine and cyanoguanidine compounds as TrkA kinase inhibitors |
| WO2014078322A1 (en) | 2012-11-13 | 2014-05-22 | Array Biopharma Inc. | Thiazolyl and oxazolyl urea, thiourea, guanidine and cyanoguanidine compounds as trka kinase inhibitors |
| US9790178B2 (en) | 2012-11-13 | 2017-10-17 | Array Biopharma Inc. | Pyrrolidinyl urea, thiourea, guanidine and cyanoguanidine compounds as TrkA kinase inhibitors |
| WO2014078408A1 (en) | 2012-11-13 | 2014-05-22 | Array Biopharma Inc. | Bicyclic heteroaryl urea, thiourea, guanidine and cyanoguanidine compounds as trka kinase inhibitors |
| PT3154959T (pt) | 2014-05-15 | 2019-09-24 | Array Biopharma Inc | 1-((3s,4r)-4-(3-fluorofenil)-1-(2-metoxietil)-pirrolidin-3-il)-3-(4-metil-3-(2-metilpirimidin-5-il)-1-fenil-1h-pirazol-5-il)ureia como inibidor da cinase trka |
| GB201721185D0 (en) | 2017-12-18 | 2018-01-31 | Nodthera Ltd | Sulphonyl urea derivatives |
| JP7523351B2 (ja) | 2018-01-31 | 2024-07-26 | デシフェラ・ファーマシューティカルズ,エルエルシー | 肥満細胞症の治療のための併用療法 |
| JP2021512105A (ja) | 2018-01-31 | 2021-05-13 | デシフェラ・ファーマシューティカルズ,エルエルシー | 消化管間質腫瘍の治療のための併用療法 |
| US11952370B2 (en) | 2018-06-11 | 2024-04-09 | Northeastern University | Selective ligands for modulation of GIRK channels |
| CN109134451A (zh) * | 2018-09-10 | 2019-01-04 | 遵义医学院 | 1,3-二取代脲类与硫脲类衍生物及其应用 |
| US11034669B2 (en) | 2018-11-30 | 2021-06-15 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| CN109456280B (zh) * | 2018-12-24 | 2020-11-10 | 锦州医科大学 | 含有脲结构的4-苯基噻唑-2-胺类衍生物及其制备方法与应用 |
| PL3983387T3 (pl) | 2019-06-12 | 2024-08-19 | NodThera Limited | Pochodne sulfonylomocznika i ich zastosowania |
| EP3999057A1 (en) | 2019-07-19 | 2022-05-25 | Anagenesis Biotechnologies Sas | Polyaromatic urea derivatives and their use in the treatment of muscle diseases |
| NZ784949A (en) | 2019-08-12 | 2025-09-26 | Deciphera Pharmaceuticals Llc | Ripretinib for treating gastrointestinal stromal tumors |
| TWI878335B (zh) | 2019-08-12 | 2025-04-01 | 美商迪賽孚爾製藥有限公司 | 治療胃腸道基質瘤方法 |
| AU2020419197B2 (en) | 2019-12-30 | 2023-08-31 | Deciphera Pharmaceuticals, Llc | Amorphous kinase inhibitor formulations and methods of use thereof |
| NZ789199A (en) | 2019-12-30 | 2025-07-25 | Deciphera Pharmaceuticals Llc | Compositions of 1-(4-bromo-5-(1-ethyl-7-(methylamino)-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2-fluorophenyl)-3-phenylurea |
| EP4029501A1 (en) | 2021-01-19 | 2022-07-20 | Anagenesis Biotechnologies | Combination of polyaromatic urea derivatives and glucocorticoid or hdac inhibitor for the treatment of diseases or conditions associated with muscle cells and/or satellite cells |
| US11779572B1 (en) | 2022-09-02 | 2023-10-10 | Deciphera Pharmaceuticals, Llc | Methods of treating gastrointestinal stromal tumors |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3818024A (en) * | 1972-02-16 | 1974-06-18 | Velsicol Chemical Corp | Benzothiazol substituted thiadiazolidines |
| US4093624A (en) * | 1977-01-31 | 1978-06-06 | Icn Pharmaceuticals, Inc. | 1,2,4-Thiadiazolidine-3,5-dione |
| US4296237A (en) * | 1979-09-11 | 1981-10-20 | Merck & Co., Inc. | 4-(Pyridyl, piperazinyl and thiazolyl substituted thiazolyl)-3-hydroxy-3-pyrroline-2,5-diones |
| US6235786B1 (en) * | 1997-08-06 | 2001-05-22 | Abbott Laboratories | Reverse hydroxamate inhibitors of matrix metalloproteinases |
| UA73492C2 (en) * | 1999-01-19 | 2005-08-15 | Aromatic heterocyclic compounds as antiinflammatory agents | |
| US6525046B1 (en) * | 2000-01-18 | 2003-02-25 | Boehringer Ingelheim Pharmaceuticals, Inc. | Aromatic heterocyclic compounds as antiinflammatory agents |
| US6645990B2 (en) * | 2000-08-15 | 2003-11-11 | Amgen Inc. | Thiazolyl urea compounds and methods of uses |
| JP2004518739A (ja) * | 2001-02-15 | 2004-06-24 | ベーリンガー インゲルハイム ファーマシューティカルズ インコーポレイテッド | 抗炎症剤として有用なヘテロアリール置換尿素化合物の合成方法 |
| CA2439263C (en) * | 2001-03-02 | 2012-10-23 | Frank Becker | Three hybrid assay system |
| US7144911B2 (en) * | 2002-12-31 | 2006-12-05 | Deciphera Pharmaceuticals Llc | Anti-inflammatory medicaments |
| US7202257B2 (en) * | 2003-12-24 | 2007-04-10 | Deciphera Pharmaceuticals, Llc | Anti-inflammatory medicaments |
| US20070191336A1 (en) * | 2003-12-24 | 2007-08-16 | Flynn Daniel L | Anti-inflammatory medicaments |
-
2005
- 2005-12-23 WO PCT/US2005/047597 patent/WO2006081034A2/en not_active Ceased
- 2005-12-23 JP JP2007548611A patent/JP2008525502A/ja not_active Abandoned
- 2005-12-23 US US11/721,026 patent/US20090312349A1/en not_active Abandoned
- 2005-12-23 AU AU2005325676A patent/AU2005325676A1/en not_active Abandoned
- 2005-12-23 EP EP05857260A patent/EP1836173A4/en not_active Withdrawn
- 2005-12-23 CA CA002592116A patent/CA2592116A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EP1836173A4 (en) | 2009-07-08 |
| US20090312349A1 (en) | 2009-12-17 |
| CA2592116A1 (en) | 2006-08-03 |
| WO2006081034A3 (en) | 2006-11-23 |
| AU2005325676A1 (en) | 2006-08-03 |
| WO2006081034A2 (en) | 2006-08-03 |
| EP1836173A2 (en) | 2007-09-26 |
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