JP2010503702A5 - - Google Patents
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- Publication number
- JP2010503702A5 JP2010503702A5 JP2009528477A JP2009528477A JP2010503702A5 JP 2010503702 A5 JP2010503702 A5 JP 2010503702A5 JP 2009528477 A JP2009528477 A JP 2009528477A JP 2009528477 A JP2009528477 A JP 2009528477A JP 2010503702 A5 JP2010503702 A5 JP 2010503702A5
- Authority
- JP
- Japan
- Prior art keywords
- dihydro
- oxo
- methyl
- methylamino
- naphthyridin
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims description 32
- -1 2-fluoro-5- (1-isopropyl-7- (methylamino) -2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl) phenyl Chemical group 0.000 claims 19
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 12
- 239000004202 carbamide Substances 0.000 claims 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims 12
- 229910052736 halogen Inorganic materials 0.000 claims 12
- 150000002367 halogens Chemical class 0.000 claims 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 12
- 239000008194 pharmaceutical composition Substances 0.000 claims 12
- 201000010099 disease Diseases 0.000 claims 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 10
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical group NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 239000003814 drug Substances 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 206010040070 Septic Shock Diseases 0.000 claims 6
- 239000002671 adjuvant Substances 0.000 claims 6
- 239000003085 diluting agent Substances 0.000 claims 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims 6
- 239000003381 stabilizer Substances 0.000 claims 6
- 229940124597 therapeutic agent Drugs 0.000 claims 5
- 206010061218 Inflammation Diseases 0.000 claims 4
- 206010027476 Metastases Diseases 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 206010040047 Sepsis Diseases 0.000 claims 4
- 208000006011 Stroke Diseases 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 230000004054 inflammatory process Effects 0.000 claims 4
- 230000009401 metastasis Effects 0.000 claims 4
- 201000008482 osteoarthritis Diseases 0.000 claims 4
- 239000000654 additive Substances 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000004452 carbocyclyl group Chemical group 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- NJVIJFIWHHXSEF-UHFFFAOYSA-N (2,3-difluorophenyl)urea Chemical compound NC(=O)NC1=CC=CC(F)=C1F NJVIJFIWHHXSEF-UHFFFAOYSA-N 0.000 claims 2
- NDPIIWGKFWKYGT-UHFFFAOYSA-N 1-[5-[1-ethyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-2-fluoro-4-methylphenyl]-3-naphthalen-1-ylurea Chemical compound C1=CC=C2C(NC(=O)NC=3C=C(C(=CC=3F)C)C3=CC4=CN=C(NC)C=C4N(C3=O)CC)=CC=CC2=C1 NDPIIWGKFWKYGT-UHFFFAOYSA-N 0.000 claims 2
- 208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims 2
- 208000014697 Acute lymphocytic leukaemia Diseases 0.000 claims 2
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 2
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims 2
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims 2
- 201000004569 Blindness Diseases 0.000 claims 2
- 206010006187 Breast cancer Diseases 0.000 claims 2
- 208000026310 Breast neoplasm Diseases 0.000 claims 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims 2
- 206010009900 Colitis ulcerative Diseases 0.000 claims 2
- 206010009944 Colon cancer Diseases 0.000 claims 2
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 2
- 206010051066 Gastrointestinal stromal tumour Diseases 0.000 claims 2
- 201000005569 Gout Diseases 0.000 claims 2
- 206010048643 Hypereosinophilic syndrome Diseases 0.000 claims 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 2
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 2
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims 2
- 206010033128 Ovarian cancer Diseases 0.000 claims 2
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 2
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 2
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims 2
- 206010060862 Prostate cancer Diseases 0.000 claims 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- 206010037660 Pyrexia Diseases 0.000 claims 2
- 206010038389 Renal cancer Diseases 0.000 claims 2
- 206010063837 Reperfusion injury Diseases 0.000 claims 2
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 2
- 208000017442 Retinal disease Diseases 0.000 claims 2
- 206010038923 Retinopathy Diseases 0.000 claims 2
- 208000024770 Thyroid neoplasm Diseases 0.000 claims 2
- 206010044248 Toxic shock syndrome Diseases 0.000 claims 2
- 231100000650 Toxic shock syndrome Toxicity 0.000 claims 2
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 2
- 230000000996 additive effect Effects 0.000 claims 2
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims 2
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 2
- 206010064930 age-related macular degeneration Diseases 0.000 claims 2
- 230000033115 angiogenesis Effects 0.000 claims 2
- 206010003246 arthritis Diseases 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 claims 2
- 208000019664 bone resorption disease Diseases 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 230000005907 cancer growth Effects 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 208000019065 cervical carcinoma Diseases 0.000 claims 2
- 208000029742 colonic neoplasm Diseases 0.000 claims 2
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 2
- 201000011243 gastrointestinal stromal tumor Diseases 0.000 claims 2
- 208000005017 glioblastoma Diseases 0.000 claims 2
- 208000024908 graft versus host disease Diseases 0.000 claims 2
- 230000003463 hyperproliferative effect Effects 0.000 claims 2
- 208000026278 immune system disease Diseases 0.000 claims 2
- 208000014674 injury Diseases 0.000 claims 2
- 208000028867 ischemia Diseases 0.000 claims 2
- 201000010982 kidney cancer Diseases 0.000 claims 2
- 201000005202 lung cancer Diseases 0.000 claims 2
- 208000020816 lung neoplasm Diseases 0.000 claims 2
- 208000002780 macular degeneration Diseases 0.000 claims 2
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 201000001441 melanoma Diseases 0.000 claims 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 210000005036 nerve Anatomy 0.000 claims 2
- 230000000926 neurological effect Effects 0.000 claims 2
- 201000002528 pancreatic cancer Diseases 0.000 claims 2
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 2
- 230000035755 proliferation Effects 0.000 claims 2
- 208000023504 respiratory system disease Diseases 0.000 claims 2
- 208000037803 restenosis Diseases 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 208000011571 secondary malignant neoplasm Diseases 0.000 claims 2
- 230000036303 septic shock Effects 0.000 claims 2
- 230000035939 shock Effects 0.000 claims 2
- 238000007920 subcutaneous administration Methods 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 230000009885 systemic effect Effects 0.000 claims 2
- 201000002510 thyroid cancer Diseases 0.000 claims 2
- 230000008733 trauma Effects 0.000 claims 2
- 230000002792 vascular Effects 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- FOXFRRGYKQNDPI-MRXNPFEDSA-N 1-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]-3-[(1r)-1-phenylethyl]urea Chemical compound C1([C@@H](C)NC(=O)NC=2C=C(C(=CC=2F)C)C=2C(=O)N(C)C=3C=C(N=CC=3C=2)NC)=CC=CC=C1 FOXFRRGYKQNDPI-MRXNPFEDSA-N 0.000 claims 1
- HKKSSFBCDUEAKI-XOBRGWDASA-N 1-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]-3-[(1s,2s)-2-methylcyclohexyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)N[C@H]1CCCC[C@@H]1C HKKSSFBCDUEAKI-XOBRGWDASA-N 0.000 claims 1
- UYZSTDZANFAJHR-UHFFFAOYSA-N 1-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]-3-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC(C(F)(F)F)=CC=C1F UYZSTDZANFAJHR-UHFFFAOYSA-N 0.000 claims 1
- GHVWBSJTPTZREA-UHFFFAOYSA-N 1-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 GHVWBSJTPTZREA-UHFFFAOYSA-N 0.000 claims 1
- XXRCQUWJSONCRT-UHFFFAOYSA-N 1-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]-3-[4-methyl-5-(trifluoromethyl)pyridin-3-yl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CN=CC(C(F)(F)F)=C1C XXRCQUWJSONCRT-UHFFFAOYSA-N 0.000 claims 1
- FPSIDFFYENCSKT-UHFFFAOYSA-N 1-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]-3-[5-(trifluoromethyl)pyridin-3-yl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CN=CC(C(F)(F)F)=C1 FPSIDFFYENCSKT-UHFFFAOYSA-N 0.000 claims 1
- AFBKZYCXZGLULN-UHFFFAOYSA-N 1-[2-fluoro-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 AFBKZYCXZGLULN-UHFFFAOYSA-N 0.000 claims 1
- PMZHKRHHUMHWRN-UHFFFAOYSA-N 1-[2-fluoro-5-[7-(methylamino)-2-oxo-1-propan-2-yl-1,6-naphthyridin-3-yl]phenyl]-3-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C(C)C)C(=O)C=1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(F)(F)F)=CC=C1F PMZHKRHHUMHWRN-UHFFFAOYSA-N 0.000 claims 1
- CNECREPZVOYSRI-UHFFFAOYSA-N 1-[4-chloro-2-fluoro-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]-3-(3-cyanophenyl)urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)Cl)=CC=1NC(=O)NC1=CC=CC(C#N)=C1 CNECREPZVOYSRI-UHFFFAOYSA-N 0.000 claims 1
- YRQKNOMICTWOEA-UHFFFAOYSA-N 1-[4-chloro-2-fluoro-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]-3-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)Cl)=CC=1NC(=O)NC1=CC(C(F)(F)F)=CC=C1F YRQKNOMICTWOEA-UHFFFAOYSA-N 0.000 claims 1
- WNQVFUGDDPHDFD-UHFFFAOYSA-N 1-[4-chloro-2-fluoro-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]-3-[4-chloro-3-(trifluoromethyl)phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)Cl)=CC=1NC(=O)NC1=CC=C(Cl)C(C(F)(F)F)=C1 WNQVFUGDDPHDFD-UHFFFAOYSA-N 0.000 claims 1
- HWSKXWLYGHRVTP-UHFFFAOYSA-N 1-[4-chloro-2-fluoro-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]-3-cyclohexylurea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)Cl)=CC=1NC(=O)NC1CCCCC1 HWSKXWLYGHRVTP-UHFFFAOYSA-N 0.000 claims 1
- HJESIEHPUXMNDW-UHFFFAOYSA-N 1-[4-chloro-2-fluoro-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]-3-naphthalen-1-ylurea Chemical compound C1=CC=C2C(NC(=O)NC=3C=C(C(=CC=3F)Cl)C=3C(=O)N(C)C=4C=C(N=CC=4C=3)NC)=CC=CC2=C1 HJESIEHPUXMNDW-UHFFFAOYSA-N 0.000 claims 1
- FGYGNBWUDFOOOY-UHFFFAOYSA-N 1-[4-chloro-2-fluoro-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]-3-phenylurea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)Cl)=CC=1NC(=O)NC1=CC=CC=C1 FGYGNBWUDFOOOY-UHFFFAOYSA-N 0.000 claims 1
- DKUXKAYWLUZKLJ-UHFFFAOYSA-N 1-[4-chloro-3-(trifluoromethyl)phenyl]-3-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC=C(Cl)C(C(F)(F)F)=C1 DKUXKAYWLUZKLJ-UHFFFAOYSA-N 0.000 claims 1
- IRBLVQHOCDLOMH-UHFFFAOYSA-N 1-[4-chloro-3-[1-ethyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]-3-cyclohexylurea Chemical compound O=C1N(CC)C2=CC(NC)=NC=C2C=C1C(C(=CC=1)Cl)=CC=1NC(=O)NC1CCCCC1 IRBLVQHOCDLOMH-UHFFFAOYSA-N 0.000 claims 1
- VWSRPILDGFSBIY-UHFFFAOYSA-N 1-[4-chloro-5-[1-ethyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-2-fluorophenyl]-3-phenylurea Chemical compound O=C1N(CC)C2=CC(NC)=NC=C2C=C1C(C(=CC=1F)Cl)=CC=1NC(=O)NC1=CC=CC=C1 VWSRPILDGFSBIY-UHFFFAOYSA-N 0.000 claims 1
- SZAZTNLBSWEIGX-UHFFFAOYSA-N 1-[5-(7-amino-1-methyl-2-oxo-1,6-naphthyridin-3-yl)-2-fluoro-4-methylphenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound C1=C(C=2C(N(C)C3=CC(N)=NC=C3C=2)=O)C(C)=CC(F)=C1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 SZAZTNLBSWEIGX-UHFFFAOYSA-N 0.000 claims 1
- GHFPWSHLGZJOGE-UHFFFAOYSA-N 1-[5-[1-ethyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-2-fluoro-4-methylphenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound O=C1N(CC)C2=CC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 GHFPWSHLGZJOGE-UHFFFAOYSA-N 0.000 claims 1
- KRKFQJUZHAFOAZ-UHFFFAOYSA-N 1-[5-[1-ethyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-2-fluorophenyl]-3-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound O=C1N(CC)C2=CC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(F)(F)F)=CC=C1F KRKFQJUZHAFOAZ-UHFFFAOYSA-N 0.000 claims 1
- MBICPGBJQCUQNW-UHFFFAOYSA-N 1-[5-[1-ethyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-2-fluorophenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound O=C1N(CC)C2=CC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 MBICPGBJQCUQNW-UHFFFAOYSA-N 0.000 claims 1
- GDENILKFMBNOQR-UHFFFAOYSA-N 1-[5-[1-ethyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-2-fluorophenyl]-3-[5-(trifluoromethyl)pyridin-3-yl]urea Chemical compound O=C1N(CC)C2=CC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CN=CC(C(F)(F)F)=C1 GDENILKFMBNOQR-UHFFFAOYSA-N 0.000 claims 1
- POCMKRLYZZZJKE-UHFFFAOYSA-N 1-[5-[1-ethyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-2-fluorophenyl]-3-naphthalen-1-ylurea Chemical compound C1=CC=C2C(NC(=O)NC=3C(F)=CC=C(C=3)C3=CC4=CN=C(NC)C=C4N(C3=O)CC)=CC=CC2=C1 POCMKRLYZZZJKE-UHFFFAOYSA-N 0.000 claims 1
- WTYGCQCRZVRKCK-UHFFFAOYSA-N 1-cyclopropyl-3-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC1CC1 WTYGCQCRZVRKCK-UHFFFAOYSA-N 0.000 claims 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- 125000001207 fluorophenyl group Chemical group 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- FVSUYFWWFUVGRG-UHFFFAOYSA-N naphthalen-1-ylurea Chemical compound C1=CC=C2C(NC(=O)N)=CC=CC2=C1 FVSUYFWWFUVGRG-UHFFFAOYSA-N 0.000 claims 1
- 238000007911 parenteral administration Methods 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
- 0 CC(*)NC(N*)=O Chemical compound CC(*)NC(N*)=O 0.000 description 17
- 230000004913 activation Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 108091000080 Phosphotransferase Proteins 0.000 description 2
- 102000020233 phosphotransferase Human genes 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- PZHASTRIYXMWKM-UHFFFAOYSA-N 3-bromo-2,6-dichloropyridine Chemical compound ClC1=CC=C(Br)C(Cl)=N1 PZHASTRIYXMWKM-UHFFFAOYSA-N 0.000 description 1
- SGCSNJNPPSSPKZ-UHFFFAOYSA-N 5-bromo-2,4-dichloropyridine Chemical compound ClC1=CC(Cl)=C(Br)C=N1 SGCSNJNPPSSPKZ-UHFFFAOYSA-N 0.000 description 1
- SIKXIUWKPGWBBF-UHFFFAOYSA-N 5-bromo-2,4-dichloropyrimidine Chemical compound ClC1=NC=C(Br)C(Cl)=N1 SIKXIUWKPGWBBF-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001336 alkenes Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000000539 amino acid group Chemical group 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000009635 nitrosylation Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000007248 oxidative elimination reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000026731 phosphorylation Effects 0.000 description 1
- 238000006366 phosphorylation reaction Methods 0.000 description 1
- QIWRFOJWQSSRJZ-UHFFFAOYSA-N tributyl(ethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=C QIWRFOJWQSSRJZ-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US84455206P | 2006-09-14 | 2006-09-14 | |
| US60/844,552 | 2006-09-14 | ||
| US11/854,354 | 2007-09-12 | ||
| US11/854,354 US8188113B2 (en) | 2006-09-14 | 2007-09-12 | Dihydropyridopyrimidinyl, dihydronaphthyidinyl and related compounds useful as kinase inhibitors for the treatment of proliferative diseases |
| PCT/US2007/078408 WO2008034008A2 (en) | 2006-09-14 | 2007-09-13 | Kinase inhibitors useful for the treatment of proliferative diseases |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010503702A JP2010503702A (ja) | 2010-02-04 |
| JP2010503702A5 true JP2010503702A5 (https=) | 2013-03-14 |
| JP5265550B2 JP5265550B2 (ja) | 2013-08-14 |
Family
ID=39184593
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009528477A Active JP5265550B2 (ja) | 2006-09-14 | 2007-09-13 | 増殖性疾患の治療に有用なキナーゼ阻害剤 |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US8188113B2 (https=) |
| EP (1) | EP2063897A4 (https=) |
| JP (1) | JP5265550B2 (https=) |
| KR (1) | KR101110530B1 (https=) |
| AU (1) | AU2007296450C1 (https=) |
| BR (2) | BR122012012032B8 (https=) |
| CA (1) | CA2663577A1 (https=) |
| EA (2) | EA026730B1 (https=) |
| MX (1) | MX2009002814A (https=) |
| WO (1) | WO2008034008A2 (https=) |
Families Citing this family (85)
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-
2007
- 2007-09-12 US US11/854,354 patent/US8188113B2/en active Active - Reinstated
- 2007-09-13 KR KR1020097007591A patent/KR101110530B1/ko not_active Expired - Fee Related
- 2007-09-13 BR BR122012012032A patent/BR122012012032B8/pt active IP Right Grant
- 2007-09-13 JP JP2009528477A patent/JP5265550B2/ja active Active
- 2007-09-13 EA EA201101341A patent/EA026730B1/ru unknown
- 2007-09-13 EP EP07842438A patent/EP2063897A4/en not_active Withdrawn
- 2007-09-13 WO PCT/US2007/078408 patent/WO2008034008A2/en not_active Ceased
- 2007-09-13 EA EA200970280A patent/EA016055B1/ru not_active IP Right Cessation
- 2007-09-13 BR BRPI0716981A patent/BRPI0716981B8/pt active IP Right Grant
- 2007-09-13 MX MX2009002814A patent/MX2009002814A/es not_active Application Discontinuation
- 2007-09-13 AU AU2007296450A patent/AU2007296450C1/en active Active
- 2007-09-13 CA CA002663577A patent/CA2663577A1/en not_active Abandoned
-
2012
- 2012-04-12 US US13/445,435 patent/US20120289540A1/en not_active Abandoned
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