JP5046950B2 - C−fmsキナーゼのインヒビター - Google Patents
C−fmsキナーゼのインヒビター Download PDFInfo
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- JP5046950B2 JP5046950B2 JP2007538060A JP2007538060A JP5046950B2 JP 5046950 B2 JP5046950 B2 JP 5046950B2 JP 2007538060 A JP2007538060 A JP 2007538060A JP 2007538060 A JP2007538060 A JP 2007538060A JP 5046950 B2 JP5046950 B2 JP 5046950B2
- Authority
- JP
- Japan
- Prior art keywords
- cyano
- carboxylic acid
- phenyl
- enyl
- amide
- 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.)
- Expired - Fee Related
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- 239000003112 inhibitor Substances 0.000 title claims description 10
- 101000916644 Homo sapiens Macrophage colony-stimulating factor 1 receptor Proteins 0.000 title 1
- 102100028198 Macrophage colony-stimulating factor 1 receptor Human genes 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 284
- -1 chloro, fluoro, methyl Chemical group 0.000 claims description 265
- 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 description 185
- 239000000203 mixture Substances 0.000 claims description 117
- 125000000217 alkyl group Chemical group 0.000 claims description 51
- 125000003277 amino group Chemical group 0.000 claims description 50
- 229910052739 hydrogen Inorganic materials 0.000 claims description 40
- 239000001257 hydrogen Substances 0.000 claims description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 38
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 36
- 229910005965 SO 2 Inorganic materials 0.000 claims description 35
- 238000011282 treatment Methods 0.000 claims description 33
- 239000012453 solvate Substances 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 30
- 229920006395 saturated elastomer Polymers 0.000 claims description 27
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims description 26
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 24
- 125000002883 imidazolyl group Chemical group 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims description 22
- 125000004076 pyridyl group Chemical group 0.000 claims description 22
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 150000002431 hydrogen Chemical class 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 125000002541 furyl group Chemical group 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 17
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 125000004122 cyclic group Chemical group 0.000 claims description 16
- 125000003282 alkyl amino group Chemical group 0.000 claims description 15
- 150000004677 hydrates Chemical class 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 108010058398 Macrophage Colony-Stimulating Factor Receptor Proteins 0.000 claims description 13
- 241000124008 Mammalia Species 0.000 claims description 13
- 206010028980 Neoplasm Diseases 0.000 claims description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 13
- 125000001153 fluoro group Chemical group F* 0.000 claims description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 12
- 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 description 12
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 12
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 12
- 125000005942 tetrahydropyridyl group Chemical group 0.000 claims description 12
- 150000001721 carbon Chemical group 0.000 claims description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical group 0.000 claims description 11
- 125000005191 hydroxyalkylamino group Chemical group 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- HHHCADSYQQJUGV-UHFFFAOYSA-N 5-cyanofuran-2-carboxylic acid Chemical compound OC(=O)C1=CC=C(C#N)O1 HHHCADSYQQJUGV-UHFFFAOYSA-N 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 125000002757 morpholinyl group Chemical group 0.000 claims description 10
- 125000003386 piperidinyl group Chemical group 0.000 claims description 10
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 10
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 9
- 201000010099 disease Diseases 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 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 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 8
- 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 claims description 8
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 8
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 125000002971 oxazolyl group Chemical group 0.000 claims description 8
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 7
- 230000000694 effects Effects 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
- FVYYZAZCLYZXQC-UHFFFAOYSA-N 5-cyano-n-[2-(2-fluorophenyl)-4-(4-methylpiperazin-1-yl)phenyl]furan-2-carboxamide Chemical compound C1CN(C)CCN1C(C=C1C=2C(=CC=CC=2)F)=CC=C1NC(=O)C1=CC=C(C#N)O1 FVYYZAZCLYZXQC-UHFFFAOYSA-N 0.000 claims description 6
- 206010006187 Breast cancer Diseases 0.000 claims description 6
- 208000026310 Breast neoplasm Diseases 0.000 claims description 6
- 206010027476 Metastases Diseases 0.000 claims description 6
- 150000001204 N-oxides Chemical class 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 6
- 125000004990 dihydroxyalkyl group Chemical group 0.000 claims description 6
- VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 6
- LJVQHXICFCZRJN-UHFFFAOYSA-N 1h-1,2,4-triazole-5-carboxylic acid Chemical compound OC(=O)C1=NC=NN1 LJVQHXICFCZRJN-UHFFFAOYSA-N 0.000 claims description 5
- GDCBIQJUSRDOGR-UHFFFAOYSA-N 5-chloro-1h-1,2,4-triazole-3-carboxylic acid Chemical compound OC(=O)C1=NNC(Cl)=N1 GDCBIQJUSRDOGR-UHFFFAOYSA-N 0.000 claims description 5
- IRZATOLKYBKBAO-UHFFFAOYSA-N 5-cyano-n-[2-(1,1-dioxo-3,6-dihydro-2h-thiopyran-4-yl)-4-piperidin-4-ylphenyl]-1h-imidazole-2-carboxamide Chemical compound N=1C(C#N)=CNC=1C(=O)NC1=CC=C(C2CCNCC2)C=C1C1=CCS(=O)(=O)CC1 IRZATOLKYBKBAO-UHFFFAOYSA-N 0.000 claims description 5
- GXQMEGDUUBFCFH-UHFFFAOYSA-N 5-cyano-n-[2-(2-methylphenyl)-4-(4-methylpiperazin-1-yl)phenyl]furan-2-carboxamide Chemical compound C1CN(C)CCN1C(C=C1C=2C(=CC=CC=2)C)=CC=C1NC(=O)C1=CC=C(C#N)O1 GXQMEGDUUBFCFH-UHFFFAOYSA-N 0.000 claims description 5
- 206010009944 Colon cancer Diseases 0.000 claims description 5
- 230000002757 inflammatory effect Effects 0.000 claims description 5
- 230000009401 metastasis Effects 0.000 claims description 5
- VHOZQGFKMQDWHA-UHFFFAOYSA-N n-[4-(1-acetylpiperidin-4-yl)-2-(1,1-dioxo-3,6-dihydro-2h-thiopyran-4-yl)phenyl]-5-cyano-1h-imidazole-2-carboxamide Chemical compound C1CN(C(=O)C)CCC1C(C=C1C=2CCS(=O)(=O)CC=2)=CC=C1NC(=O)C1=NC(C#N)=CN1 VHOZQGFKMQDWHA-UHFFFAOYSA-N 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
- 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 description 4
- VTVVSHJUELMWBZ-UHFFFAOYSA-N 5-cyano-n-[2-(3,6-dihydro-2h-pyran-4-yl)-4-(4-methylpiperazin-1-yl)phenyl]furan-2-carboxamide Chemical compound C1CN(C)CCN1C(C=C1C=2CCOCC=2)=CC=C1NC(=O)C1=CC=C(C#N)O1 VTVVSHJUELMWBZ-UHFFFAOYSA-N 0.000 claims description 4
- JJZWAMOLUCACLS-UHFFFAOYSA-N 5-cyano-n-[2-(cyclohexen-1-yl)-4-[1-[2-[2-hydroxyethyl(methyl)amino]acetyl]piperidin-4-yl]phenyl]-1h-imidazole-2-carboxamide Chemical compound C1CN(C(=O)CN(CCO)C)CCC1C(C=C1C=2CCCCC=2)=CC=C1NC(=O)C1=NC(C#N)=CN1 JJZWAMOLUCACLS-UHFFFAOYSA-N 0.000 claims description 4
- BKGAAMAFOWYKJB-UHFFFAOYSA-N 5-cyano-n-[4-(4-methylpiperazin-1-yl)-2-(3-methylthiophen-2-yl)phenyl]furan-2-carboxamide Chemical compound C1CN(C)CCN1C(C=C1C2=C(C=CS2)C)=CC=C1NC(=O)C1=CC=C(C#N)O1 BKGAAMAFOWYKJB-UHFFFAOYSA-N 0.000 claims description 4
- 206010033128 Ovarian cancer Diseases 0.000 claims description 4
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 4
- 230000033115 angiogenesis Effects 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- BUZRUIZTMOKRPB-UHFFFAOYSA-N carboxycarbamic acid Chemical compound OC(=O)NC(O)=O BUZRUIZTMOKRPB-UHFFFAOYSA-N 0.000 claims description 4
- 208000029742 colonic neoplasm Diseases 0.000 claims description 4
- 206010012601 diabetes mellitus Diseases 0.000 claims description 4
- YEEBLJFZYXYIOQ-UHFFFAOYSA-N 5-cyano-n-[2-(cyclohexen-1-yl)-4-[1-(2-morpholin-4-ylacetyl)piperidin-4-yl]phenyl]-1h-imidazole-2-carboxamide Chemical compound C1CC(C=2C=C(C(NC(=O)C=3NC=C(N=3)C#N)=CC=2)C=2CCCCC=2)CCN1C(=O)CN1CCOCC1 YEEBLJFZYXYIOQ-UHFFFAOYSA-N 0.000 claims description 3
- WQWMJNBXEBZCOT-UHFFFAOYSA-N 5-cyano-n-[2-(cyclopenten-1-yl)-4-[1-[(1-methylimidazol-2-yl)methyl]piperidin-4-yl]phenyl]-1h-imidazole-2-carboxamide Chemical compound CN1C=CN=C1CN1CCC(C=2C=C(C(NC(=O)C=3NC=C(N=3)C#N)=CC=2)C=2CCCC=2)CC1 WQWMJNBXEBZCOT-UHFFFAOYSA-N 0.000 claims description 3
- FXFXHNQBLWHYDI-UHFFFAOYSA-N 5-cyano-n-[2-(cyclopenten-1-yl)-4-piperidin-4-ylphenyl]-1h-imidazole-2-carboxamide Chemical compound N=1C(C#N)=CNC=1C(=O)NC1=CC=C(C2CCNCC2)C=C1C1=CCCC1 FXFXHNQBLWHYDI-UHFFFAOYSA-N 0.000 claims description 3
- ZWRCMAAVANOLOT-UHFFFAOYSA-N 5-cyano-n-[4-(4-methylpiperazin-1-yl)-2-(2-methylthiophen-3-yl)phenyl]furan-2-carboxamide Chemical compound C1CN(C)CCN1C(C=C1C2=C(SC=C2)C)=CC=C1NC(=O)C1=CC=C(C#N)O1 ZWRCMAAVANOLOT-UHFFFAOYSA-N 0.000 claims description 3
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- 239000003937 drug carrier Substances 0.000 claims description 3
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- 206010017758 gastric cancer Diseases 0.000 claims description 3
- 201000009277 hairy cell leukemia Diseases 0.000 claims description 3
- GCPYRLIYCNLRAT-UHFFFAOYSA-N n-[4-(1-acetylpiperidin-4-yl)-2-(1,2,3,6-tetrahydropyridin-5-yl)phenyl]-5-cyano-1h-imidazole-2-carboxamide Chemical compound C1CN(C(=O)C)CCC1C(C=C1C=2CNCCC=2)=CC=C1NC(=O)C1=NC(C#N)=CN1 GCPYRLIYCNLRAT-UHFFFAOYSA-N 0.000 claims description 3
- WVJQGZYKOZGBMB-UHFFFAOYSA-N n-[4-[1-(3-amino-3-methylbutanoyl)piperidin-4-yl]-2-(cyclohexen-1-yl)phenyl]-5-cyano-1h-imidazole-2-carboxamide;2,2,2-trifluoroacetic acid Chemical class OC(=O)C(F)(F)F.C1CN(C(=O)CC(C)(N)C)CCC1C(C=C1C=2CCCCC=2)=CC=C1NC(=O)C1=NC(C#N)=CN1 WVJQGZYKOZGBMB-UHFFFAOYSA-N 0.000 claims description 3
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- 210000000988 bone and bone Anatomy 0.000 claims description 2
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- FFASJWSCBGYXQX-UHFFFAOYSA-N n-[4-[1-(2-amino-2-methylpropanoyl)piperidin-4-yl]-2-(cyclohexen-1-yl)phenyl]-5-cyano-1h-imidazole-2-carboxamide;2,2,2-trifluoroacetic acid Chemical class OC(=O)C(F)(F)F.C1CN(C(=O)C(C)(N)C)CCC1C(C=C1C=2CCCCC=2)=CC=C1NC(=O)C1=NC=C(C#N)N1 FFASJWSCBGYXQX-UHFFFAOYSA-N 0.000 claims description 2
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- 239000004480 active ingredient Substances 0.000 claims 9
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 279
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- 238000004007 reversed phase HPLC Methods 0.000 description 16
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- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D401/14—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 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
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| US60/621,211 | 2004-10-22 | ||
| PCT/US2005/037868 WO2006047277A2 (en) | 2004-10-22 | 2005-10-20 | Inhibitors of c-fms kinase |
Publications (3)
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2009534418A (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−kitキナーゼ阻害法 |
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| EP1631560A2 (en) | 2003-04-25 | 2006-03-08 | 3-Dimensional Pharmaceuticals, Inc. | C-fms kinase inhibitors |
| US7427683B2 (en) | 2003-04-25 | 2008-09-23 | Ortho-Mcneil Pharmaceutical, Inc. | c-fms kinase inhibitors |
| US7790724B2 (en) | 2003-04-25 | 2010-09-07 | Janssen Pharmaceutica N.V. | c-fms kinase inhibitors |
| TW200526626A (en) | 2003-09-13 | 2005-08-16 | Astrazeneca Ab | Chemical compounds |
| JP5008569B2 (ja) * | 2004-10-22 | 2012-08-22 | 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キナーゼのインヒビターとしての芳香族アミド |
| WO2006087543A1 (en) | 2005-02-18 | 2006-08-24 | Astrazeneca Ab | Antibacterial piperidine derivatives |
| US20080269214A1 (en) * | 2005-03-04 | 2008-10-30 | Astrazeneca Ab | Pyrrole Derivatives as Dna Gyrase and Topoisomerase Inhibitors |
| JP2008540665A (ja) * | 2005-05-19 | 2008-11-20 | 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 | イオンチャネルのモジュレーターとして有用なビアリール |
| EP1904491A2 (en) | 2005-05-31 | 2008-04-02 | Vertex Pharmaceuticals Incorporated | Heterocycles useful as modulators of ion channels |
| 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 |
| US20070004660A1 (en) * | 2005-06-10 | 2007-01-04 | Baumann Christian A | Synergistic Modulation of Flt3 Kinase Using Alkylquinolines and Alkylquinazolines |
| EP1951234A2 (en) * | 2005-10-18 | 2008-08-06 | Janssen Pharmaceutica N.V. | Method of inhibiting flt3 kinase |
| KR101367645B1 (ko) * | 2006-04-20 | 2014-02-27 | 얀센 파마슈티카 엔.브이. | C-fms 키나제의 저해제로서의 복소환식 화합물 |
| US8697716B2 (en) * | 2006-04-20 | 2014-04-15 | Janssen Pharmaceutica Nv | Method of inhibiting C-KIT kinase |
| KR101367646B1 (ko) | 2006-04-20 | 2014-02-27 | 얀센 파마슈티카 엔.브이. | C-fms 키나제의 저해제 |
| 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 |
| JP5443342B2 (ja) | 2007-06-08 | 2014-03-19 | 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 | ピペリジン/ピペラジン誘導体 |
| AU2008258487B2 (en) | 2007-06-08 | 2012-11-15 | Janssen Pharmaceutica N.V. | Piperidine/piperazine derivatives |
| JP5464709B2 (ja) | 2007-06-08 | 2014-04-09 | 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 | ピペリジン/ピペラジン誘導体 |
| JO2972B1 (en) | 2007-06-08 | 2016-03-15 | جانسين فارماسوتيكا ان. في | Piperidine / piperazine derivatives |
| JO3240B1 (ar) * | 2007-10-17 | 2018-03-08 | Janssen Pharmaceutica Nv | c-fms مثبطات كيناز |
| AU2013203813B2 (en) * | 2007-10-17 | 2014-07-31 | Janssen Pharmaceutica, N.V. | Inhibitors of C-FMS kinase |
| CA2704517A1 (en) * | 2007-11-02 | 2009-05-07 | Janssen Pharmaceutica, N.V. | Use of cfms inhibitor for treating or preventing bone cancer and the bone loss and bone pain associated with bone cancer |
| TWI498115B (zh) | 2007-12-27 | 2015-09-01 | Daiichi Sankyo Co Ltd | 咪唑羰基化合物 |
| ES2617619T3 (es) | 2008-06-05 | 2017-06-19 | Janssen Pharmaceutica, N.V. | Combinaciones de fármacos que comprenden un inhibidor de DGAT y un agonista de PPAR |
| WO2011149841A1 (en) | 2010-05-25 | 2011-12-01 | Janssen Pharmaceutica Nv | SUBSTITUTED THIAZOLIDINEDIONE INDAZOLES, INDOLES AND BENZOTRIAZOLES AS ESTROGEN-RELATED RECEPTOR-α MODULATORS |
| DK2822656T3 (en) | 2012-03-07 | 2017-01-30 | Inst Of Cancer Research: Royal Cancer Hospital (The) | 3-aryl-5-substituted-isoquinolin-1-one compounds and their therapeutic use |
| US9303046B2 (en) | 2012-08-07 | 2016-04-05 | Janssen Pharmaceutica Nv | Process for the preparation of heterocyclic ester derivatives |
| JOP20180012A1 (ar) | 2012-08-07 | 2019-01-30 | Janssen Pharmaceutica Nv | عملية السلفنة باستخدام نونافلوروبوتانيسولفونيل فلوريد |
| KR101676208B1 (ko) * | 2012-09-17 | 2016-11-14 | 에프. 호프만-라 로슈 아게 | 트라이아졸 카복스아미드 유도체 |
| CN103664957A (zh) * | 2012-09-25 | 2014-03-26 | 杨子娇 | 一类治疗房角狭窄的化合物及其用途 |
| CN103804349A (zh) * | 2012-11-01 | 2014-05-21 | 杨子娇 | 一类治疗青光眼的化合物及其用途 |
| CN104370881A (zh) * | 2013-01-24 | 2015-02-25 | 韩冰 | 一类具有神经保护作用的化合物及其制备方法和用途 |
| CN104370882A (zh) * | 2013-01-24 | 2015-02-25 | 韩冰 | 一类降低眼压的化合物及其制备方法和用途 |
| CN104370880A (zh) * | 2013-01-24 | 2015-02-25 | 韩冰 | 一类蛋白酶抑制剂及其制备方法和用途 |
| ES2662600T3 (es) | 2013-03-15 | 2018-04-09 | Janssen Pharmaceutica, N.V. | Derivados de piridina sustituidos útiles como inhibidores de c-fms quinasa |
| PL3024832T3 (pl) | 2013-07-22 | 2018-10-31 | Idorsia Pharmaceuticals Ltd | Pochodne 1-(piperazyn-1-ylo)-2-([1,2,4]triazol-1-ilo)-etanonu |
| CN105722835B (zh) | 2013-09-11 | 2018-07-31 | 癌症研究协会:皇家癌症医院 | 3-芳基-5-取代的-异喹啉-1-酮化合物及它们的疗法应用 |
| PL3245203T3 (pl) | 2015-01-15 | 2019-05-31 | Idorsia Pharmaceuticals Ltd | Pochodne hydroksyalkilopiperazyny jako modulatory receptora cxcr3 |
| AR103399A1 (es) | 2015-01-15 | 2017-05-10 | Actelion Pharmaceuticals Ltd | Derivados de (r)-2-metil-piperazina como moduladores del receptor cxcr3 |
| JP7012822B2 (ja) * | 2017-08-10 | 2022-02-14 | 中国科学院上海薬物研究所 | フタラジノン系化合物、その製造方法、医薬組成物及びその使用 |
| US10930064B2 (en) | 2018-02-08 | 2021-02-23 | Covidien Lp | Imaging reconstruction system and method |
| AU2019407650B2 (en) | 2018-12-17 | 2022-10-27 | Tolremo Therapeutics Ag | Heterocyclic derivatives, pharmaceutical compositions and their use in the treatment, amelioration or prevention of cancer |
| WO2021144360A1 (en) | 2020-01-17 | 2021-07-22 | F. Hoffmann-La Roche Ag | Small molecule csf-1r inhibitors in therapeutic and cosmetic uses |
| WO2024254440A1 (en) * | 2023-06-09 | 2024-12-12 | Modulo Bio, Inc. | 5-cyano-1h-imidazole-2-carboxamide compounds as csf1r inhibitors |
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| GB9523675D0 (en) * | 1995-11-20 | 1996-01-24 | Celltech Therapeutics Ltd | Chemical compounds |
| JP2002520324A (ja) * | 1998-07-10 | 2002-07-09 | メルク エンド カムパニー インコーポレーテッド | 新規な血管形成インヒビター |
| GB9824579D0 (en) * | 1998-11-10 | 1999-01-06 | Novartis Ag | Organic compounds |
| EP1140938B1 (en) * | 1999-01-11 | 2003-08-27 | Princeton University | High affinity inhibitors for target validation and uses thereof |
| CA2396693A1 (en) * | 1999-12-28 | 2001-07-05 | Stephen T. Wrobleski | Cytokine, especially tnf-alpha, inhibitors |
| US7105682B2 (en) * | 2001-01-12 | 2006-09-12 | Amgen Inc. | Substituted amine derivatives and methods of use |
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| US20050113566A1 (en) * | 2003-04-25 | 2005-05-26 | Player Mark R. | Inhibitors of C-FMS kinase |
| EP1631560A2 (en) * | 2003-04-25 | 2006-03-08 | 3-Dimensional Pharmaceuticals, Inc. | C-fms kinase inhibitors |
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| EP1951234A2 (en) * | 2005-10-18 | 2008-08-06 | Janssen Pharmaceutica N.V. | Method of inhibiting flt3 kinase |
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2007
- 2007-05-15 NO NO20072489A patent/NO339555B1/no not_active IP Right Cessation
- 2007-05-21 ZA ZA200704106A patent/ZA200704106B/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009534418A (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−kitキナーゼ阻害法 |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2005299837A1 (en) | 2006-05-04 |
| BRPI0516947A (pt) | 2008-09-23 |
| ZA200704106B (en) | 2009-09-30 |
| EP1807077A2 (en) | 2007-07-18 |
| KR20070085382A (ko) | 2007-08-27 |
| ES2611604T3 (es) | 2017-05-09 |
| UA88648C2 (en) | 2009-11-10 |
| DK1807077T3 (en) | 2017-01-23 |
| NO20072489L (no) | 2007-06-29 |
| EA200700918A1 (ru) | 2008-06-30 |
| MX2007004784A (es) | 2007-09-11 |
| HUE033089T2 (en) | 2017-11-28 |
| JP2008517926A (ja) | 2008-05-29 |
| WO2006047277A2 (en) | 2006-05-04 |
| KR101273434B1 (ko) | 2013-06-11 |
| WO2006047277A3 (en) | 2009-05-07 |
| CA2585053C (en) | 2011-07-12 |
| EP1807077A4 (en) | 2011-09-21 |
| CA2585053A1 (en) | 2006-05-04 |
| PL1807077T3 (pl) | 2017-05-31 |
| CN101437514A (zh) | 2009-05-20 |
| CN101437514B (zh) | 2012-04-25 |
| EA013250B1 (ru) | 2010-04-30 |
| EP1807077B1 (en) | 2016-11-23 |
| NO339555B1 (no) | 2017-01-02 |
| PT1807077T (pt) | 2017-01-06 |
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