JP2010510242A - キナーゼ阻害剤としてのスルホキシミン - Google Patents
キナーゼ阻害剤としてのスルホキシミン Download PDFInfo
- Publication number
- JP2010510242A JP2010510242A JP2009537394A JP2009537394A JP2010510242A JP 2010510242 A JP2010510242 A JP 2010510242A JP 2009537394 A JP2009537394 A JP 2009537394A JP 2009537394 A JP2009537394 A JP 2009537394A JP 2010510242 A JP2010510242 A JP 2010510242A
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- methyl
- ethynyl
- sulfanilidene
- nicotinamide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 125000005555 sulfoximide group Chemical group 0.000 title claims description 5
- 229940043355 kinase inhibitor Drugs 0.000 title description 2
- 239000003757 phosphotransferase inhibitor Substances 0.000 title description 2
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims abstract description 23
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims abstract description 23
- 230000011664 signaling Effects 0.000 claims abstract description 17
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 436
- -1 carboalkyl Chemical class 0.000 claims description 379
- 150000001875 compounds Chemical class 0.000 claims description 295
- 235000005152 nicotinamide Nutrition 0.000 claims description 209
- 239000011570 nicotinamide Substances 0.000 claims description 209
- 229960003966 nicotinamide Drugs 0.000 claims description 209
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 159
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 152
- 239000000203 mixture Substances 0.000 claims description 92
- 238000000034 method Methods 0.000 claims description 78
- 125000000217 alkyl group Chemical group 0.000 claims description 57
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 55
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 45
- 229910052739 hydrogen Inorganic materials 0.000 claims description 39
- 229910052736 halogen Inorganic materials 0.000 claims description 38
- 150000002367 halogens Chemical class 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 38
- 239000001257 hydrogen Substances 0.000 claims description 36
- 150000002431 hydrogen Chemical class 0.000 claims description 28
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 27
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 26
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 125000000623 heterocyclic group Chemical group 0.000 claims description 20
- 229910052717 sulfur Inorganic materials 0.000 claims description 20
- 229910004013 NO 2 Inorganic materials 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
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- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 201000010099 disease Diseases 0.000 claims description 12
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- 150000003973 alkyl amines Chemical class 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 11
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- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 10
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- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 9
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- 230000002062 proliferating effect Effects 0.000 claims description 8
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 7
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 7
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- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
- 206010012689 Diabetic retinopathy Diseases 0.000 claims description 5
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims description 5
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- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 5
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- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 4
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- 206010003246 arthritis Diseases 0.000 claims description 4
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000002837 carbocyclic group Chemical group 0.000 claims description 4
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- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
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- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 3
- 206010016654 Fibrosis Diseases 0.000 claims description 3
- 102000004278 Receptor Protein-Tyrosine Kinases Human genes 0.000 claims description 3
- 108090000873 Receptor Protein-Tyrosine Kinases Proteins 0.000 claims description 3
- 206010038933 Retinopathy of prematurity Diseases 0.000 claims description 3
- 206010064930 age-related macular degeneration Diseases 0.000 claims description 3
- 125000003435 aroyl group Chemical group 0.000 claims description 3
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- 230000004770 neurodegeneration Effects 0.000 claims description 3
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- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 2
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- 230000007882 cirrhosis Effects 0.000 claims description 2
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- 230000004054 inflammatory process Effects 0.000 claims description 2
- 230000029663 wound healing Effects 0.000 claims description 2
- DFPAKSUCGFBDDF-ZQBYOMGUSA-N [14c]-nicotinamide Chemical compound N[14C](=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-ZQBYOMGUSA-N 0.000 claims 31
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 4
- 125000005189 alkyl hydroxy group Chemical group 0.000 claims 4
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 4
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 3
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 claims 2
- ZCCPVTVGEQLONB-UHFFFAOYSA-N 1-(1,3-dioxolan-2-yl)-n-methylmethanamine Chemical compound CNCC1OCCO1 ZCCPVTVGEQLONB-UHFFFAOYSA-N 0.000 claims 2
- QAFODUGVXFNLBE-UHFFFAOYSA-N 1-methoxybutan-2-amine Chemical compound CCC(N)COC QAFODUGVXFNLBE-UHFFFAOYSA-N 0.000 claims 2
- ZUUQKDDUUOFCNP-UHFFFAOYSA-N 2-(1,3-dioxolan-2-yl)-n-methylethanamine Chemical compound CNCCC1OCCO1 ZUUQKDDUUOFCNP-UHFFFAOYSA-N 0.000 claims 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 2
- KDHWOCLBMVSZPG-UHFFFAOYSA-N 3-imidazol-1-ylpropan-1-amine Chemical compound NCCCN1C=CN=C1 KDHWOCLBMVSZPG-UHFFFAOYSA-N 0.000 claims 2
- 125000004364 3-pyrrolinyl group Chemical group [H]C1=C([H])C([H])([H])N(*)C1([H])[H] 0.000 claims 2
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 2
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims 2
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims 2
- RZVWBASHHLFBJF-UHFFFAOYSA-N methyl piperidine-4-carboxylate Chemical compound COC(=O)C1CCNCC1 RZVWBASHHLFBJF-UHFFFAOYSA-N 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- AHVQYHFYQWKUKB-UHFFFAOYSA-N oxan-4-amine Chemical compound NC1CCOCC1 AHVQYHFYQWKUKB-UHFFFAOYSA-N 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 2
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 1
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 1
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- 206010018364 Glomerulonephritis Diseases 0.000 claims 1
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- 208000033679 diabetic kidney disease Diseases 0.000 claims 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 1
- 230000003211 malignant effect Effects 0.000 claims 1
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- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 230000010261 cell growth Effects 0.000 abstract description 7
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 394
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 127
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 87
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- WZTBDEAKUXWNAK-UHFFFAOYSA-N methyl 2-[3-[n-(5-bromopyridine-3-carbonyl)-s-methylsulfonimidoyl]phenyl]acetate Chemical compound COC(=O)CC1=CC=CC(S(C)(=O)=NC(=O)C=2C=C(Br)C=NC=2)=C1 WZTBDEAKUXWNAK-UHFFFAOYSA-N 0.000 description 2
- LGUOHYJFLHAQCK-UHFFFAOYSA-N methyl 2-[3-[n-[5-[2-[3-[(2,5-dimethylpyrazole-3-carbonyl)amino]phenyl]ethynyl]pyridine-3-carbonyl]-s-phenylsulfonimidoyl]propylamino]-3-hydroxypropanoate Chemical compound C=1C=CC=CC=1S(=O)(CCCNC(CO)C(=O)OC)=NC(=O)C(C=1)=CN=CC=1C#CC(C=1)=CC=CC=1NC(=O)C1=CC(C)=NN1C LGUOHYJFLHAQCK-UHFFFAOYSA-N 0.000 description 2
- YPMUNUHZCOSGHP-UHFFFAOYSA-N methyl 2-[3-[n-[6-amino-5-[2-[3-[(2,5-dimethylpyrazole-3-carbonyl)amino]phenyl]ethynyl]pyridine-3-carbonyl]-s-methylsulfonimidoyl]phenyl]acetate Chemical compound COC(=O)CC1=CC=CC(S(C)(=O)=NC(=O)C=2C=C(C(N)=NC=2)C#CC=2C=C(NC(=O)C=3N(N=C(C)C=3)C)C=CC=2)=C1 YPMUNUHZCOSGHP-UHFFFAOYSA-N 0.000 description 2
- RUZLIIJDZBWWSA-INIZCTEOSA-N methyl 2-[[(1s)-1-(7-methyl-2-morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)ethyl]amino]benzoate Chemical group COC(=O)C1=CC=CC=C1N[C@@H](C)C1=CC(C)=CN2C(=O)C=C(N3CCOCC3)N=C12 RUZLIIJDZBWWSA-INIZCTEOSA-N 0.000 description 2
- LXZAFOHXMUDYNN-UHFFFAOYSA-N methyl 3-(4-methylsulfanylphenyl)propanoate Chemical compound COC(=O)CCC1=CC=C(SC)C=C1 LXZAFOHXMUDYNN-UHFFFAOYSA-N 0.000 description 2
- IUSFTGHXPJPIMZ-UHFFFAOYSA-N methyl 3-[4-[n-[5-[2-[3-[(2,5-dimethylpyrazole-3-carbonyl)amino]phenyl]ethynyl]pyridine-3-carbonyl]-s-methylsulfonimidoyl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1S(C)(=O)=NC(=O)C1=CN=CC(C#CC=2C=C(NC(=O)C=3N(N=C(C)C=3)C)C=CC=2)=C1 IUSFTGHXPJPIMZ-UHFFFAOYSA-N 0.000 description 2
- YBRRKBFXJWGQMR-UHFFFAOYSA-N methyl 3-[4-[s-methyl-n-(2,2,2-trifluoroacetyl)sulfonimidoyl]phenyl]propanoate Chemical compound COC(=O)CCC1=CC=C(S(C)(=O)=NC(=O)C(F)(F)F)C=C1 YBRRKBFXJWGQMR-UHFFFAOYSA-N 0.000 description 2
- JCMYTFIDZIHMNQ-UHFFFAOYSA-N methyl 3-[n-(5-bromopyridine-3-carbonyl)-s-methylsulfonimidoyl]benzoate Chemical compound COC(=O)C1=CC=CC(S(C)(=O)=NC(=O)C=2C=C(Br)C=NC=2)=C1 JCMYTFIDZIHMNQ-UHFFFAOYSA-N 0.000 description 2
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- KDRAZQCILSSTFK-UHFFFAOYSA-N methyl 3-[n-[6-amino-5-[2-[3-[(2,5-dimethylpyrazole-3-carbonyl)amino]phenyl]ethynyl]pyridine-3-carbonyl]-s-methylsulfonimidoyl]benzoate Chemical compound COC(=O)C1=CC=CC(S(C)(=O)=NC(=O)C=2C=C(C(N)=NC=2)C#CC=2C=C(NC(=O)C=3N(N=C(C)C=3)C)C=CC=2)=C1 KDRAZQCILSSTFK-UHFFFAOYSA-N 0.000 description 2
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- IRRRLJBJCYLJNF-IBGZPJMESA-N tert-butyl-dimethyl-[3-(phenylsulfonimidoyl)propoxy]silane Chemical compound CC(C)(C)[Si](C)(C)OCCC[S@](=N)(=O)C1=CC=CC=C1 IRRRLJBJCYLJNF-IBGZPJMESA-N 0.000 description 1
- 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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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- 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
- C07D413/06—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 linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US86608006P | 2006-11-16 | 2006-11-16 | |
| PCT/US2007/084999 WO2008061236A2 (en) | 2006-11-16 | 2007-11-16 | Sulfoximines as kinase inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2010510242A true JP2010510242A (ja) | 2010-04-02 |
| JP2010510242A5 JP2010510242A5 (enExample) | 2010-11-18 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009537394A Pending JP2010510242A (ja) | 2006-11-16 | 2007-11-16 | キナーゼ阻害剤としてのスルホキシミン |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7915443B2 (enExample) |
| EP (1) | EP2099757B1 (enExample) |
| JP (1) | JP2010510242A (enExample) |
| AU (1) | AU2007319151B2 (enExample) |
| BR (1) | BRPI0718895A2 (enExample) |
| CA (1) | CA2669704A1 (enExample) |
| WO (1) | WO2008061236A2 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012524750A (ja) * | 2009-04-21 | 2012-10-18 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 5−アルキニル−ピリジン |
| JP2016539995A (ja) * | 2013-12-12 | 2016-12-22 | アラーガン、インコーポレイテッドAllergan,Incorporated | キナーゼ阻害剤としての置換ニコチンアミド誘導体 |
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| US7456476B2 (en) | 2003-06-27 | 2008-11-25 | Intel Corporation | Nonplanar semiconductor device with partially or fully wrapped around gate electrode and methods of fabrication |
| US8455656B2 (en) | 2004-04-30 | 2013-06-04 | Allergan, Inc. | Kinase inhibitors |
| WO2005107708A1 (en) | 2004-04-30 | 2005-11-17 | Allergan, Inc. | Biodegradable intravitreal tyrosine kinase inhibitors implants |
| US7771742B2 (en) | 2004-04-30 | 2010-08-10 | Allergan, Inc. | Sustained release intraocular implants containing tyrosine kinase inhibitors and related methods |
| US7042009B2 (en) | 2004-06-30 | 2006-05-09 | Intel Corporation | High mobility tri-gate devices and methods of fabrication |
| US20060086977A1 (en) | 2004-10-25 | 2006-04-27 | Uday Shah | Nonplanar device with thinned lower body portion and method of fabrication |
| US7518196B2 (en) | 2005-02-23 | 2009-04-14 | Intel Corporation | Field effect transistor with narrow bandgap source and drain regions and method of fabrication |
| US7858481B2 (en) | 2005-06-15 | 2010-12-28 | Intel Corporation | Method for fabricating transistor with thinned channel |
| US7547637B2 (en) | 2005-06-21 | 2009-06-16 | Intel Corporation | Methods for patterning a semiconductor film |
| US7279375B2 (en) * | 2005-06-30 | 2007-10-09 | Intel Corporation | Block contact architectures for nanoscale channel transistors |
| US20070090416A1 (en) | 2005-09-28 | 2007-04-26 | Doyle Brian S | CMOS devices with a single work function gate electrode and method of fabrication |
| US7485503B2 (en) | 2005-11-30 | 2009-02-03 | Intel Corporation | Dielectric interface for group III-V semiconductor device |
| WO2007087419A2 (en) | 2006-01-24 | 2007-08-02 | Allergan, Inc. | Substituted 3-(5-membered unsaturated heterocyclyl) -1, 3-dihydro-indol-2-one derivatives as tyrosine kinase inhibitors for the treatment of cancer |
| US8143646B2 (en) | 2006-08-02 | 2012-03-27 | Intel Corporation | Stacking fault and twin blocking barrier for integrating III-V on Si |
| US8558002B2 (en) * | 2006-11-16 | 2013-10-15 | Allergan, Inc. | Sulfoximines as kinase inhibitors |
| US8143410B2 (en) * | 2006-11-16 | 2012-03-27 | Allergan, Inc. | Kinase inhibitors |
| US8642067B2 (en) * | 2007-04-02 | 2014-02-04 | Allergen, Inc. | Methods and compositions for intraocular administration to treat ocular conditions |
| US8362566B2 (en) | 2008-06-23 | 2013-01-29 | Intel Corporation | Stress in trigate devices using complimentary gate fill materials |
| US20100278897A1 (en) * | 2009-05-01 | 2010-11-04 | Allergan, Inc. | Intraocular bioactive agent delivery system with molecular partitioning system |
| KR20160096174A (ko) * | 2013-12-12 | 2016-08-12 | 알러간, 인코포레이티드 | 키나제 저해제로서의 치환된 다이알킬(옥사이도)-λ⁴-설판일리덴 니코틴아마이드 유도체 |
| CN111662227B (zh) * | 2019-03-06 | 2022-07-05 | 中国科学院上海药物研究所 | 邻氨基吡啶炔类化合物及其制备方法和用途 |
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- 2007-11-16 JP JP2009537394A patent/JP2010510242A/ja active Pending
- 2007-11-16 AU AU2007319151A patent/AU2007319151B2/en not_active Ceased
- 2007-11-16 BR BRPI0718895-1A patent/BRPI0718895A2/pt not_active IP Right Cessation
- 2007-11-16 CA CA002669704A patent/CA2669704A1/en not_active Abandoned
- 2007-11-16 EP EP07864544.7A patent/EP2099757B1/en not_active Not-in-force
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| JP2011503178A (ja) * | 2007-11-15 | 2011-01-27 | アストラゼネカ・アクチエボラーグ | 治療066におけるビス−(スルホニルアミノ)誘導体 |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012524750A (ja) * | 2009-04-21 | 2012-10-18 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 5−アルキニル−ピリジン |
| US9090564B2 (en) | 2009-04-21 | 2015-07-28 | Boehringer Ingelheim International Gmbh | 5-alkynyl-pyridines |
| JP2016539995A (ja) * | 2013-12-12 | 2016-12-22 | アラーガン、インコーポレイテッドAllergan,Incorporated | キナーゼ阻害剤としての置換ニコチンアミド誘導体 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2099757A2 (en) | 2009-09-16 |
| HK1134674A1 (en) | 2010-05-07 |
| BRPI0718895A2 (pt) | 2013-12-10 |
| WO2008061236A3 (en) | 2008-07-31 |
| US7915443B2 (en) | 2011-03-29 |
| US20090099181A1 (en) | 2009-04-16 |
| AU2007319151B2 (en) | 2013-05-23 |
| AU2007319151A1 (en) | 2008-05-22 |
| EP2099757B1 (en) | 2014-06-25 |
| WO2008061236A2 (en) | 2008-05-22 |
| CA2669704A1 (en) | 2008-05-22 |
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