JP2008517945A5 - - Google Patents
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- Publication number
- JP2008517945A5 JP2008517945A5 JP2007538165A JP2007538165A JP2008517945A5 JP 2008517945 A5 JP2008517945 A5 JP 2008517945A5 JP 2007538165 A JP2007538165 A JP 2007538165A JP 2007538165 A JP2007538165 A JP 2007538165A JP 2008517945 A5 JP2008517945 A5 JP 2008517945A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- piperidin
- cyano
- carboxylic acid
- phenyl
- 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
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- -1 chloro, fluoro, methyl Chemical group 0.000 claims 49
- 150000001875 compounds Chemical class 0.000 claims 19
- HHHCADSYQQJUGV-UHFFFAOYSA-N 5-cyanofuran-2-carboxylic acid Chemical compound OC(=O)C1=CC=C(C#N)O1 HHHCADSYQQJUGV-UHFFFAOYSA-N 0.000 claims 18
- 125000000217 alkyl group Chemical group 0.000 claims 13
- SAEZQFNKTQKVSM-UHFFFAOYSA-N 4-cyano-1h-pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC(C#N)=CN1 SAEZQFNKTQKVSM-UHFFFAOYSA-N 0.000 claims 10
- 125000003277 amino group Chemical group 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 10
- 239000004480 active ingredient Substances 0.000 claims 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims 9
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 9
- 125000003386 piperidinyl group Chemical group 0.000 claims 9
- 125000004076 pyridyl group Chemical group 0.000 claims 8
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 7
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 7
- 125000002883 imidazolyl group Chemical group 0.000 claims 7
- 229910052757 nitrogen Inorganic materials 0.000 claims 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 6
- 125000003282 alkyl amino group Chemical group 0.000 claims 6
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 241000124008 Mammalia Species 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000004122 cyclic group Chemical group 0.000 claims 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 5
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 150000001408 amides Chemical class 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 125000002541 furyl group Chemical group 0.000 claims 4
- 125000005191 hydroxyalkylamino group Chemical group 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000002757 morpholinyl group Chemical group 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims 4
- VMJNTFXCTXAXTC-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxole-5-carbonitrile Chemical group C1=C(C#N)C=C2OC(F)(F)OC2=C1 VMJNTFXCTXAXTC-UHFFFAOYSA-N 0.000 claims 3
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims 3
- 206010027476 Metastases Diseases 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims 3
- KYWMCFOWDYFYLV-UHFFFAOYSA-N 1h-imidazole-2-carboxylic acid Chemical compound OC(=O)C1=NC=CN1 KYWMCFOWDYFYLV-UHFFFAOYSA-N 0.000 claims 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 2
- XTDRPNJABDWQFI-UHFFFAOYSA-N 5-cyano-1h-imidazole-2-carboxylic acid Chemical compound OC(=O)C1=NC(C#N)=CN1 XTDRPNJABDWQFI-UHFFFAOYSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 208000037408 Device failure Diseases 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- 208000037099 Prosthesis Failure Diseases 0.000 claims 2
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims 2
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 150000001721 carbon Chemical group 0.000 claims 2
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims 2
- 125000004990 dihydroxyalkyl group Chemical group 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000002552 dosage form Substances 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical group 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 230000002757 inflammatory effect Effects 0.000 claims 2
- 239000003112 inhibitor Substances 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- 230000009401 metastasis Effects 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- NKWCGTOZTHZDHB-UHFFFAOYSA-N 1h-imidazol-1-ium-4-carboxylate Chemical compound OC(=O)C1=CNC=N1 NKWCGTOZTHZDHB-UHFFFAOYSA-N 0.000 claims 1
- ZUUNZDIGHGJBAR-UHFFFAOYSA-N 1h-imidazole-2,5-dicarboxylic acid Chemical compound OC(=O)C1=CNC(C(O)=O)=N1 ZUUNZDIGHGJBAR-UHFFFAOYSA-N 0.000 claims 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- LZVKCYRGBCITFS-UHFFFAOYSA-N 2-(dimethylamino)ethyl 4-[4-[(4-cyano-1h-pyrrole-2-carbonyl)amino]-3-(4-methylpiperidin-1-yl)phenyl]piperidine-1-carboxylate Chemical compound C1CC(C)CCN1C1=CC(C2CCN(CC2)C(=O)OCCN(C)C)=CC=C1NC(=O)C1=CC(C#N)=CN1 LZVKCYRGBCITFS-UHFFFAOYSA-N 0.000 claims 1
- DXPSQKSTVIVZLV-UHFFFAOYSA-N 4-cyano-N-[4-(4-methyl-1-piperazinyl)-2-(4-methyl-1-piperidinyl)phenyl]-1H-pyrrole-2-carboxamide Chemical compound C1CC(C)CCN1C1=CC(N2CCN(C)CC2)=CC=C1NC(=O)C1=CC(C#N)=CN1 DXPSQKSTVIVZLV-UHFFFAOYSA-N 0.000 claims 1
- NZRFILSWDBFAQV-UHFFFAOYSA-N 4-cyano-n-[4-(4-methylpiperazin-1-yl)-2-piperidin-1-ylphenyl]-1h-pyrrole-2-carboxamide Chemical compound C1CN(C)CCN1C(C=C1N2CCCCC2)=CC=C1NC(=O)C1=CC(C#N)=CN1 NZRFILSWDBFAQV-UHFFFAOYSA-N 0.000 claims 1
- KNWWGBNAUNTSRV-UHFFFAOYSA-N 4-methylpiperazine-1-carboxylic acid Chemical compound CN1CCN(C(O)=O)CC1 KNWWGBNAUNTSRV-UHFFFAOYSA-N 0.000 claims 1
- MYCIMLZPBNXTCG-UHFFFAOYSA-N 5-cyano-n-(2-piperidin-1-yl-4-thiomorpholin-4-ylphenyl)furan-2-carboxamide Chemical compound C=1C=C(C#N)OC=1C(=O)NC1=CC=C(N2CCSCC2)C=C1N1CCCCC1 MYCIMLZPBNXTCG-UHFFFAOYSA-N 0.000 claims 1
- AXLZQSZTRSYXTN-UHFFFAOYSA-N 5-cyano-n-(5-morpholin-4-yl-2-piperidin-1-ylphenyl)furan-2-carboxamide Chemical compound C=1C=C(C#N)OC=1C(=O)NC1=CC(N2CCOCC2)=CC=C1N1CCCCC1 AXLZQSZTRSYXTN-UHFFFAOYSA-N 0.000 claims 1
- UUUKVTZIWPSPDX-UHFFFAOYSA-N 5-cyano-n-[2-(4-fluoropiperidin-1-yl)-4-(4-methylpiperazin-1-yl)phenyl]furan-2-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1CN(C)CCN1C(C=C1N2CCC(F)CC2)=CC=C1NC(=O)C1=CC=C(C#N)O1 UUUKVTZIWPSPDX-UHFFFAOYSA-N 0.000 claims 1
- RQFFOLKOUGRFPD-UHFFFAOYSA-N 5-cyano-n-[2-(4-methylpiperidin-1-yl)-4-(1,2,3,6-tetrahydropyridin-4-yl)phenyl]furan-2-carboxamide Chemical compound C1CC(C)CCN1C1=CC(C=2CCNCC=2)=CC=C1NC(=O)C1=CC=C(C#N)O1 RQFFOLKOUGRFPD-UHFFFAOYSA-N 0.000 claims 1
- REJFXXBFQUSFTH-UHFFFAOYSA-N 5-cyano-n-[2-(4-methylpiperidin-1-yl)-4-(4-methylsulfonylpiperazin-1-yl)phenyl]furan-2-carboxamide Chemical compound C1CC(C)CCN1C1=CC(N2CCN(CC2)S(C)(=O)=O)=CC=C1NC(=O)C1=CC=C(C#N)O1 REJFXXBFQUSFTH-UHFFFAOYSA-N 0.000 claims 1
- FAGARJGZRYAALA-UHFFFAOYSA-N 5-cyano-n-[2-(4-methylpiperidin-1-yl)-4-morpholin-4-ylphenyl]furan-2-carboxamide Chemical compound C1CC(C)CCN1C1=CC(N2CCOCC2)=CC=C1NC(=O)C1=CC=C(C#N)O1 FAGARJGZRYAALA-UHFFFAOYSA-N 0.000 claims 1
- VPVJZBBTXRKDKI-UHFFFAOYSA-N 5-cyano-n-[4-(4-methylpiperazin-1-yl)-2-(4-methylpiperidin-1-yl)phenyl]furan-2-carboxamide Chemical compound C1CC(C)CCN1C1=CC(N2CCN(C)CC2)=CC=C1NC(=O)C1=CC=C(C#N)O1 VPVJZBBTXRKDKI-UHFFFAOYSA-N 0.000 claims 1
- RSSFHMINUIZERF-UHFFFAOYSA-N 5-cyano-n-[4-(4-methylpiperazin-1-yl)-2-piperidin-1-ylphenyl]-1h-imidazole-2-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1CN(C)CCN1C(C=C1N2CCCCC2)=CC=C1NC(=O)C1=NC=C(C#N)N1 RSSFHMINUIZERF-UHFFFAOYSA-N 0.000 claims 1
- RKXHDVVOVIGWRP-UHFFFAOYSA-N 5-cyano-n-[4-(4-methylpiperazin-1-yl)-2-piperidin-1-ylphenyl]furan-2-carboxamide;hydrochloride Chemical compound Cl.C1CN(C)CCN1C(C=C1N2CCCCC2)=CC=C1NC(=O)C1=CC=C(C#N)O1 RKXHDVVOVIGWRP-UHFFFAOYSA-N 0.000 claims 1
- UBRSJBGFUCCGDM-UHFFFAOYSA-N 5-cyano-n-[4-(methanesulfonamido)-2-piperidin-1-ylphenyl]furan-2-carboxamide Chemical compound C1CCCCN1C1=CC(NS(=O)(=O)C)=CC=C1NC(=O)C1=CC=C(C#N)O1 UBRSJBGFUCCGDM-UHFFFAOYSA-N 0.000 claims 1
- WKEZULBZMKJKNX-UHFFFAOYSA-N 5-cyano-n-[4-[methyl(methylsulfonyl)amino]-2-piperidin-1-ylphenyl]furan-2-carboxamide Chemical compound C1CCCCN1C1=CC(N(C)S(C)(=O)=O)=CC=C1NC(=O)C1=CC=C(C#N)O1 WKEZULBZMKJKNX-UHFFFAOYSA-N 0.000 claims 1
- PKECJMKGEABNJF-UHFFFAOYSA-N 5-cyano-n-[5-(4-methylpiperazin-1-yl)-3-(4-methylpiperidin-1-yl)pyrazin-2-yl]furan-2-carboxamide Chemical compound C1CC(C)CCN1C1=NC(N2CCN(C)CC2)=CN=C1NC(=O)C1=CC=C(C#N)O1 PKECJMKGEABNJF-UHFFFAOYSA-N 0.000 claims 1
- CSYFKZQGYVXBHS-UHFFFAOYSA-N 5-cyano-n-[5-fluoro-4-(4-methylpiperazin-1-yl)-2-(4-methylpiperidin-1-yl)phenyl]furan-2-carboxamide Chemical compound C1CC(C)CCN1C1=CC(N2CCN(C)CC2)=C(F)C=C1NC(=O)C1=CC=C(C#N)O1 CSYFKZQGYVXBHS-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 208000006386 Bone Resorption Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 1
- WDMOUGKDVXOPJZ-UHFFFAOYSA-N FC(C(=O)O)(F)F.FC(C(=O)O)(F)F.FC(C(=O)O)(F)F.FC1CN(CCC1)C1=C(C=CC(=C1)N1CCN(CC1)C)N.C(#N)C=1N=C(NC1)C(=O)O Chemical compound FC(C(=O)O)(F)F.FC(C(=O)O)(F)F.FC(C(=O)O)(F)F.FC1CN(CCC1)C1=C(C=CC(=C1)N1CCN(CC1)C)N.C(#N)C=1N=C(NC1)C(=O)O WDMOUGKDVXOPJZ-UHFFFAOYSA-N 0.000 claims 1
- 206010018364 Glomerulonephritis Diseases 0.000 claims 1
- 208000031886 HIV Infections Diseases 0.000 claims 1
- 208000037357 HIV infectious disease Diseases 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 206010065390 Inflammatory pain Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 108010058398 Macrophage Colony-Stimulating Factor Receptor Proteins 0.000 claims 1
- 150000001204 N-oxides Chemical class 0.000 claims 1
- 208000011623 Obstructive Lung disease Diseases 0.000 claims 1
- 208000010191 Osteitis Deformans Diseases 0.000 claims 1
- 208000001132 Osteoporosis Diseases 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
- 208000027868 Paget disease Diseases 0.000 claims 1
- 206010033645 Pancreatitis Diseases 0.000 claims 1
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 206010039491 Sarcoma Diseases 0.000 claims 1
- 208000021386 Sjogren Syndrome Diseases 0.000 claims 1
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
- 208000002495 Uterine Neoplasms Diseases 0.000 claims 1
- 206010046851 Uveitis Diseases 0.000 claims 1
- NFSGWCMDSHRSEW-UHFFFAOYSA-N [2-[4-[(5-cyanofuran-2-carbonyl)amino]-3-piperidin-1-ylanilino]-2-oxoethyl] acetate Chemical compound C1CCCCN1C1=CC(NC(=O)COC(=O)C)=CC=C1NC(=O)C1=CC=C(C#N)O1 NFSGWCMDSHRSEW-UHFFFAOYSA-N 0.000 claims 1
- 206010064930 age-related macular degeneration Diseases 0.000 claims 1
- 230000033115 angiogenesis Effects 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- DNYJFBMGSYUDNZ-UHFFFAOYSA-N benzyl 4-[4-[(5-cyanofuran-2-carbonyl)amino]-3-(4-methylpiperidin-1-yl)phenyl]piperazine-1-carboxylate Chemical compound C1CC(C)CCN1C1=CC(N2CCN(CC2)C(=O)OCC=2C=CC=CC=2)=CC=C1NC(=O)C1=CC=C(C#N)O1 DNYJFBMGSYUDNZ-UHFFFAOYSA-N 0.000 claims 1
- 210000000988 bone and bone Anatomy 0.000 claims 1
- 230000024279 bone resorption Effects 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- BUZRUIZTMOKRPB-UHFFFAOYSA-N carboxycarbamic acid Chemical compound OC(=O)NC(O)=O BUZRUIZTMOKRPB-UHFFFAOYSA-N 0.000 claims 1
- 208000029742 colonic neoplasm Diseases 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- QEWYKACRFQMRMB-UHFFFAOYSA-N fluoroacetic acid Chemical compound OC(=O)CF QEWYKACRFQMRMB-UHFFFAOYSA-N 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 201000009277 hairy cell leukemia Diseases 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 201000005296 lung carcinoma Diseases 0.000 claims 1
- 208000002780 macular degeneration Diseases 0.000 claims 1
- 208000027202 mammary Paget disease Diseases 0.000 claims 1
- VNHOHBCZUYJUHU-UHFFFAOYSA-N methyl 4-[[4-(4-methylpiperazin-1-yl)-2-piperidin-1-ylphenyl]carbamoyl]-1,3-oxazole-2-carboxylate Chemical compound O1C(C(=O)OC)=NC(C(=O)NC=2C(=CC(=CC=2)N2CCN(C)CC2)N2CCCCC2)=C1 VNHOHBCZUYJUHU-UHFFFAOYSA-N 0.000 claims 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 201000000050 myeloid neoplasm Diseases 0.000 claims 1
- ZGIBTICZYWOPFJ-UHFFFAOYSA-N n-(4-azido-2-piperidin-1-ylphenyl)-5-cyanofuran-2-carboxamide Chemical compound C1CCCCN1C1=CC(N=[N+]=[N-])=CC=C1NC(=O)C1=CC=C(C#N)O1 ZGIBTICZYWOPFJ-UHFFFAOYSA-N 0.000 claims 1
- YZXJSCBHIVTUNY-UHFFFAOYSA-N n-[2,4-di(piperidin-1-yl)phenyl]-5-(n'-hydroxycarbamimidoyl)furan-2-carboxamide Chemical compound O1C(C(=N)NO)=CC=C1C(=O)NC1=CC=C(N2CCCCC2)C=C1N1CCCCC1 YZXJSCBHIVTUNY-UHFFFAOYSA-N 0.000 claims 1
- LXNSFOLMNZRZMW-UHFFFAOYSA-N n-[4-(1-acetylpiperidin-4-yl)-2-(4-methylpiperidin-1-yl)phenyl]-5-cyanofuran-2-carboxamide Chemical compound C1CC(C)CCN1C1=CC(C2CCN(CC2)C(C)=O)=CC=C1NC(=O)C1=CC=C(C#N)O1 LXNSFOLMNZRZMW-UHFFFAOYSA-N 0.000 claims 1
- QGPHKAQQVJRELW-UHFFFAOYSA-N n-[4-(4-acetylpiperazin-1-yl)-2-(4-methylpiperidin-1-yl)phenyl]-4-cyano-1h-pyrrole-2-carboxamide Chemical compound C1CC(C)CCN1C1=CC(N2CCN(CC2)C(C)=O)=CC=C1NC(=O)C1=CC(C#N)=CN1 QGPHKAQQVJRELW-UHFFFAOYSA-N 0.000 claims 1
- CMSBCDSRGYAHEW-UHFFFAOYSA-N n-[4-(4-acetylpiperazin-1-yl)-2-(4-methylpiperidin-1-yl)phenyl]-5-cyanofuran-2-carboxamide Chemical compound C1CC(C)CCN1C1=CC(N2CCN(CC2)C(C)=O)=CC=C1NC(=O)C1=CC=C(C#N)O1 CMSBCDSRGYAHEW-UHFFFAOYSA-N 0.000 claims 1
- 208000004296 neuralgia Diseases 0.000 claims 1
- 208000021722 neuropathic pain Diseases 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 230000000010 osteolytic effect Effects 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 230000001575 pathological effect Effects 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 208000037803 restenosis Diseases 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 201000000306 sarcoidosis Diseases 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 230000009885 systemic effect Effects 0.000 claims 1
- YMGQDRFGJAEEGX-UHFFFAOYSA-N tert-butyl 4-[4-[(5-cyanofuran-2-carbonyl)amino]-3-(4-methylpiperidin-1-yl)phenyl]piperazine-1-carboxylate Chemical compound C1CC(C)CCN1C1=CC(N2CCN(CC2)C(=O)OC(C)(C)C)=CC=C1NC(=O)C1=CC=C(C#N)O1 YMGQDRFGJAEEGX-UHFFFAOYSA-N 0.000 claims 1
- XKXIQBVKMABYQJ-UHFFFAOYSA-N tert-butyl hydrogen carbonate Chemical compound CC(C)(C)OC(O)=O XKXIQBVKMABYQJ-UHFFFAOYSA-N 0.000 claims 1
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 1
- 206010046766 uterine cancer Diseases 0.000 claims 1
- 230000009278 visceral effect Effects 0.000 claims 1
- 0 C**C*N(CC=C(C)C1)C1(O)O Chemical compound C**C*N(CC=C(C)C1)C1(O)O 0.000 description 4
- IYTUMWMQDZVGBP-UHFFFAOYSA-N CC(CN(C)C1)N(C)C1O Chemical compound CC(CN(C)C1)N(C)C1O IYTUMWMQDZVGBP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US62119204P | 2004-10-22 | 2004-10-22 | |
| US60/621,192 | 2004-10-22 | ||
| PCT/US2005/038341 WO2006047504A1 (en) | 2004-10-22 | 2005-10-20 | Aromatic amides as inhibitors of c-fms kinase |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008517945A JP2008517945A (ja) | 2008-05-29 |
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| US7790724B2 (en) | 2003-04-25 | 2010-09-07 | Janssen Pharmaceutica N.V. | c-fms kinase inhibitors |
| US7427683B2 (en) * | 2003-04-25 | 2008-09-23 | Ortho-Mcneil Pharmaceutical, Inc. | c-fms kinase inhibitors |
| MXPA05011503A (es) | 2003-04-25 | 2006-05-31 | Johnson & Johnson | Inhibidores de la c-fms cinasa. |
| TW200526626A (en) | 2003-09-13 | 2005-08-16 | Astrazeneca Ab | Chemical compounds |
| CN101437514B (zh) * | 2004-10-22 | 2012-04-25 | 詹森药业有限公司 | C-fms激酶抑制剂 |
| EP1676842A1 (en) * | 2004-12-30 | 2006-07-05 | Laboratorios Del Dr. Esteve, S.A. | Nitro-substituted phenyl-piperazine compounds, their preparation and use in medicaments |
| ES2430569T3 (es) | 2005-02-18 | 2013-11-21 | Astrazeneca Ab | Compuestos antibacterianos derivados de piperidina |
| US20080269214A1 (en) * | 2005-03-04 | 2008-10-30 | Astrazeneca Ab | Pyrrole Derivatives as Dna Gyrase and Topoisomerase 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 |
| NL2000284C2 (nl) * | 2005-11-04 | 2007-09-28 | Pfizer Ltd | Pyrazine-derivaten. |
| JP5182088B2 (ja) * | 2006-04-19 | 2013-04-10 | アステラス製薬株式会社 | アゾールカルボキサミド誘導体 |
| EP2016070B1 (en) | 2006-04-20 | 2016-01-13 | Janssen Pharmaceutica N.V. | Inhibitors of c-fms kinase |
| KR101367645B1 (ko) | 2006-04-20 | 2014-02-27 | 얀센 파마슈티카 엔.브이. | Ｃ-ｆｍｓ 키나제의 저해제로서의 복소환식 화합물 |
| JP2009534380A (ja) * | 2006-04-20 | 2009-09-24 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | ｃ−ｆｍｓキナーゼインヒビター |
| EP2021329B1 (en) * | 2006-04-20 | 2016-04-13 | Janssen Pharmaceutica N.V. | Inhibitors of c-fms kinase |
| US8697716B2 (en) | 2006-04-20 | 2014-04-15 | Janssen Pharmaceutica Nv | Method of inhibiting C-KIT kinase |
| JO3240B1 (ar) * | 2007-10-17 | 2018-03-08 | Janssen Pharmaceutica Nv | c-fms مثبطات كيناز |
| SI2206707T1 (sl) | 2007-10-24 | 2014-11-28 | Astellas Pharma Inc. | Azolkarboksamidna spojina ali njena sol |
| TWI498115B (zh) * | 2007-12-27 | 2015-09-01 | Daiichi Sankyo Co Ltd | 咪唑羰基化合物 |
| PL3354650T3 (pl) | 2008-12-19 | 2022-06-13 | Vertex Pharmaceuticals Incorporated | Związki przydatne jako inhibitory kinazy atr |
| EP2475656A1 (en) * | 2009-09-07 | 2012-07-18 | NeuroSearch A/S | 2, 3, 6 -triamino substituted pyridines as kv7 (kcnq) channel modulators |
| JP2013526540A (ja) | 2010-05-12 | 2013-06-24 | バーテックス ファーマシューティカルズ インコーポレイテッド | Ａｔｒキナーゼ阻害剤として有用な化合物 |
| WO2011143423A2 (en) * | 2010-05-12 | 2011-11-17 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of atr kinase |
| JP5836367B2 (ja) | 2010-05-12 | 2015-12-24 | バーテックス ファーマシューティカルズ インコーポレイテッドＶｅｒｔｅｘ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃｏｒｐｏｒａｔｅｄ | Ａｔｒキナーゼ阻害剤として有用な化合物 |
| EP2627650A2 (en) * | 2010-05-26 | 2013-08-21 | Merck Sharp & Dohme Corp. | N-phenyl imidazole carboxamide inhibitors of 3-phosphoinositide-dependent protein kinase-1 |
| RU2018147217A (ru) | 2011-09-30 | 2019-01-18 | Вертекс Фармасьютикалз Инкорпорейтед | Способы получения соединений, которые можно использовать в качестве ингибиторов киназы atr |
| AU2012315384B2 (en) | 2011-09-30 | 2017-08-10 | Vertex Pharmaceuticals Incorporated | Treating pancreatic cancer and non-small cell lung cancer with ATR inhibitors |
| CN104582795B (zh) | 2012-04-05 | 2018-04-20 | 沃泰克斯药物股份有限公司 | 可用作atr激酶抑制剂的化合物及其组合疗法 |
| ES2607807T3 (es) * | 2012-08-07 | 2017-04-04 | Janssen Pharmaceutica Nv | Procedimiento para la preparación de los inibidores de las quinasas c-fms |
| AU2013299922B2 (en) | 2012-08-07 | 2018-06-21 | Janssen Pharmaceutica Nv | Process for the preparation of heterocyclic ester derivatives |
| DK2904406T3 (en) | 2012-10-04 | 2018-06-18 | Vertex Pharma | METHOD OF DETERMINING THE ATR INHIBITION, INCREASED DNA DAMAGE |
| EP3063134B1 (en) * | 2013-11-01 | 2020-08-12 | Srf Limited | Process for the preparation of pyrazole derivatives |
| US11464774B2 (en) | 2015-09-30 | 2022-10-11 | Vertex Pharmaceuticals Incorporated | Method for treating cancer using a combination of DNA damaging agents and ATR inhibitors |
| WO2020006075A1 (en) * | 2018-06-26 | 2020-01-02 | The Johns Hopkins University | Positron emission tomography (pet) radiotracers for imaging macrophage colony-stimulating factor 1 receptor (csf1r) in neuroinflammation |
| US10959987B2 (en) | 2019-04-15 | 2021-03-30 | King Abdulaziz University | Imidazole-based compounds as hepatitis C virus inhibitors |
| WO2021144360A1 (en) | 2020-01-17 | 2021-07-22 | F. Hoffmann-La Roche Ag | Small molecule csf-1r inhibitors in therapeutic and cosmetic uses |
| CN117337292A (zh) * | 2021-05-12 | 2024-01-02 | 勃林格殷格翰国际有限公司 | 作为cGAS抑制剂的具有N-连接环状取代基的吡啶衍生物 |
| CN115707699B (zh) * | 2021-08-18 | 2025-08-19 | 中国医学科学院医药生物技术研究所 | 一组抗骨质疏松的化合物及其应用 |
| US20260062416A1 (en) * | 2022-08-12 | 2026-03-05 | Accent Therapeutics, Inc. | Inhibitors of kif18a and uses thereof |
| AU2024214768A1 (en) * | 2023-01-30 | 2025-08-07 | The Johns Hopkins University | 18 f-labeled pet radiotracers for imaging macrophage colony stimulating factor 1 receptor |
| CN118027009B (zh) * | 2024-04-15 | 2024-07-12 | 北京师范大学 | 一类靶向于csf1r激酶的苯基酰胺类化合物及其应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5700823A (en) * | 1994-01-07 | 1997-12-23 | Sugen, Inc. | Treatment of platelet derived growth factor related disorders such as cancers |
| US7105682B2 (en) * | 2001-01-12 | 2006-09-12 | Amgen Inc. | Substituted amine derivatives and methods of use |
| CZ20032233A3 (cs) * | 2001-02-20 | 2004-12-15 | Bristol-Myers Squibb Company | Derivát 2,4-disubstituovaného pyrimidin-5-karboxamidu jako modulátor draslíkového kanálku KCNQ |
| WO2003103658A1 (ja) * | 2002-06-05 | 2003-12-18 | 株式会社医薬分子設計研究所 | 免疫関連プロテインキナーゼ阻害剤 |
| MXPA05011503A (es) | 2003-04-25 | 2006-05-31 | Johnson & Johnson | Inhibidores de la c-fms cinasa. |
| US20050113566A1 (en) * | 2003-04-25 | 2005-05-26 | Player Mark R. | Inhibitors of C-FMS kinase |
| US7427683B2 (en) * | 2003-04-25 | 2008-09-23 | Ortho-Mcneil Pharmaceutical, Inc. | c-fms kinase inhibitors |
| WO2005073193A1 (en) * | 2004-01-23 | 2005-08-11 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments |
| CN101437514B (zh) * | 2004-10-22 | 2012-04-25 | 詹森药业有限公司 | C-fms激酶抑制剂 |
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- 2005-10-20 JP JP2007538165A patent/JP5008569B2/ja not_active Expired - Fee Related
- 2005-10-20 EP EP05814104A patent/EP1807407B1/en not_active Expired - Lifetime
- 2005-10-20 US US11/255,043 patent/US7705042B2/en not_active Expired - Fee Related
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- 2005-10-20 DE DE602005015742T patent/DE602005015742D1/de not_active Expired - Fee Related
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- 2005-10-20 AT AT05814104T patent/ATE437864T1/de not_active IP Right Cessation
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