JP4865702B2 - サイトカイン阻害剤 - Google Patents
サイトカイン阻害剤 Download PDFInfo
- Publication number
- JP4865702B2 JP4865702B2 JP2007511450A JP2007511450A JP4865702B2 JP 4865702 B2 JP4865702 B2 JP 4865702B2 JP 2007511450 A JP2007511450 A JP 2007511450A JP 2007511450 A JP2007511450 A JP 2007511450A JP 4865702 B2 JP4865702 B2 JP 4865702B2
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- methyl
- optionally
- alkoxy
- 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.)
- Expired - Fee Related
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- 102000004127 Cytokines Human genes 0.000 title description 44
- 108090000695 Cytokines Proteins 0.000 title description 44
- 239000003112 inhibitor Substances 0.000 title description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 244
- 150000001875 compounds Chemical class 0.000 claims description 99
- 125000003545 alkoxy group Chemical group 0.000 claims description 81
- -1 hydroxy, hydroxy Chemical group 0.000 claims description 75
- 229910052739 hydrogen Inorganic materials 0.000 claims description 56
- 239000001257 hydrogen Substances 0.000 claims description 54
- 125000000623 heterocyclic group Chemical group 0.000 claims description 48
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 42
- 150000002431 hydrogen Chemical class 0.000 claims description 39
- 125000003118 aryl group Chemical group 0.000 claims description 36
- 150000002825 nitriles Chemical class 0.000 claims description 36
- 125000002252 acyl group Chemical group 0.000 claims description 35
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 35
- 125000001072 heteroaryl group Chemical group 0.000 claims description 34
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 33
- 229910052736 halogen Inorganic materials 0.000 claims description 32
- 150000002367 halogens Chemical class 0.000 claims description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
- 125000003342 alkenyl group Chemical group 0.000 claims description 29
- 125000003282 alkyl amino group Chemical group 0.000 claims description 29
- 125000004043 oxo group Chemical group O=* 0.000 claims description 29
- 125000003386 piperidinyl group Chemical group 0.000 claims description 28
- 125000002757 morpholinyl group Chemical group 0.000 claims description 27
- 125000004076 pyridyl group Chemical group 0.000 claims description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 23
- 125000004193 piperazinyl group Chemical group 0.000 claims description 23
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 23
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 22
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
- 125000002883 imidazolyl group Chemical group 0.000 claims description 17
- JNFIHXJPZSKVII-UHFFFAOYSA-N 1-methyl-7-pyridin-4-yloxyindole-2-carboxylic acid Chemical compound C=12N(C)C(C(O)=O)=CC2=CC=CC=1OC1=CC=NC=C1 JNFIHXJPZSKVII-UHFFFAOYSA-N 0.000 claims description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 125000004423 acyloxy group Chemical group 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 16
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 15
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 14
- 125000004442 acylamino group Chemical group 0.000 claims description 14
- 125000000304 alkynyl group Chemical group 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000001425 triazolyl group Chemical group 0.000 claims description 13
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 12
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 11
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 11
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 11
- 150000001356 alkyl thiols Chemical class 0.000 claims description 10
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 9
- 125000002971 oxazolyl group Chemical group 0.000 claims description 9
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 9
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 9
- 125000000335 thiazolyl group Chemical group 0.000 claims description 9
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 9
- WCNFFKHKJLERFM-UHFFFAOYSA-N thiomorpholinyl sulfone group Chemical group N1(CCSCC1)S(=O)(=O)N1CCSCC1 WCNFFKHKJLERFM-UHFFFAOYSA-N 0.000 claims description 9
- ZCAGUOCUDGWENZ-UHFFFAOYSA-N thiomorpholinyl sulfoxide group Chemical group N1(CCSCC1)S(=O)N1CCSCC1 ZCAGUOCUDGWENZ-UHFFFAOYSA-N 0.000 claims description 9
- 150000001408 amides Chemical class 0.000 claims description 7
- 125000004069 aziridinyl group Chemical group 0.000 claims description 7
- 125000002541 furyl group Chemical group 0.000 claims description 7
- 125000001422 pyrrolinyl group Chemical group 0.000 claims description 7
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 7
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 7
- FFFYPQJYPMJWJY-UHFFFAOYSA-N 1-methyl-7-[2-(4-methylpiperazin-1-yl)pyridin-4-yl]oxyindole-2-carboxylic acid Chemical compound C1CN(C)CCN1C1=CC(OC=2C=3N(C)C(C(O)=O)=CC=3C=CC=2)=CC=N1 FFFYPQJYPMJWJY-UHFFFAOYSA-N 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 5
- 125000005940 1,4-dioxanyl group Chemical group 0.000 claims description 5
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 5
- YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 claims description 5
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 5
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 5
- 125000004276 dioxalanyl group Chemical group 0.000 claims description 5
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 5
- 125000001041 indolyl group Chemical group 0.000 claims description 5
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 5
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 5
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 5
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 5
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 5
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 5
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 5
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 claims description 5
- ISXOBTBCNRIIQO-UHFFFAOYSA-N tetrahydrothiophene 1-oxide Chemical compound O=S1CCCC1 ISXOBTBCNRIIQO-UHFFFAOYSA-N 0.000 claims description 5
- BUGOPWGPQGYYGR-UHFFFAOYSA-N thiane 1,1-dioxide Chemical compound O=S1(=O)CCCCC1 BUGOPWGPQGYYGR-UHFFFAOYSA-N 0.000 claims description 5
- NNLBRYQGMOYARS-UHFFFAOYSA-N thiane 1-oxide Chemical compound O=S1CCCCC1 NNLBRYQGMOYARS-UHFFFAOYSA-N 0.000 claims description 5
- YFHICDDUDORKJB-UHFFFAOYSA-N trimethylene carbonate Chemical compound O=C1OCCCO1 YFHICDDUDORKJB-UHFFFAOYSA-N 0.000 claims description 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
- 125000003435 aroyl group Chemical group 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000005605 benzo group Chemical group 0.000 claims description 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
- PJQFFBWOBHJRSE-UHFFFAOYSA-N n-(5-tert-butyl-2-methylpyridin-3-yl)-1-methyl-7-pyridin-4-yloxyindole-2-carboxamide Chemical compound CC1=NC=C(C(C)(C)C)C=C1NC(=O)C1=CC2=CC=CC(OC=3C=CN=CC=3)=C2N1C PJQFFBWOBHJRSE-UHFFFAOYSA-N 0.000 claims description 2
- FNYZOSLTEFIJEE-UHFFFAOYSA-N n-(5-tert-butyl-2-methylsulfinylphenyl)-1-methyl-7-pyridin-4-yloxyindole-2-carboxamide Chemical compound C=12N(C)C(C(=O)NC=3C(=CC=C(C=3)C(C)(C)C)S(C)=O)=CC2=CC=CC=1OC1=CC=NC=C1 FNYZOSLTEFIJEE-UHFFFAOYSA-N 0.000 claims description 2
- RQKSFNAHXUEHEM-UHFFFAOYSA-N n-(5-tert-butyl-2-methylsulfonylphenyl)-1-methyl-7-pyridin-4-yloxyindole-2-carboxamide Chemical compound C=12N(C)C(C(=O)NC=3C(=CC=C(C=3)C(C)(C)C)S(C)(=O)=O)=CC2=CC=CC=1OC1=CC=NC=C1 RQKSFNAHXUEHEM-UHFFFAOYSA-N 0.000 claims description 2
- QXMRVSNDXLZRDT-UHFFFAOYSA-N n-(5-tert-butyl-2-oxo-1h-pyridin-3-yl)-1-methyl-7-pyridin-4-yloxyindole-2-carboxamide Chemical compound C=12N(C)C(C(=O)NC=3C(NC=C(C=3)C(C)(C)C)=O)=CC2=CC=CC=1OC1=CC=NC=C1 QXMRVSNDXLZRDT-UHFFFAOYSA-N 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
- 150000003536 tetrazoles Chemical class 0.000 claims description 2
- 150000003852 triazoles Chemical class 0.000 claims description 2
- 230000003796 beauty Effects 0.000 claims 2
- CDKZKAUOODOSCT-UHFFFAOYSA-N 1-methyl-7-[2-(4-methylpiperazin-1-yl)pyrimidin-4-yl]oxyindole-2-carboxylic acid Chemical compound C1CN(C)CCN1C1=NC=CC(OC=2C=3N(C)C(C(O)=O)=CC=3C=CC=2)=N1 CDKZKAUOODOSCT-UHFFFAOYSA-N 0.000 claims 1
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- SQLZBXYFLQKKFE-UHFFFAOYSA-N n-(2-tert-butyl-5-methoxypyridin-4-yl)-1-methyl-7-[2-(4-methylpiperazin-1-yl)pyrimidin-4-yl]oxyindole-2-carboxamide Chemical compound COC1=CN=C(C(C)(C)C)C=C1NC(=O)C1=CC2=CC=CC(OC=3N=C(N=CC=3)N3CCN(C)CC3)=C2N1C SQLZBXYFLQKKFE-UHFFFAOYSA-N 0.000 claims 1
- RGEHOVSPXMOFJS-UHFFFAOYSA-N n-(2-tert-butyl-5-methylsulfinylpyridin-4-yl)-1-methyl-7-[2-(4-methylpiperazin-1-yl)pyridin-4-yl]oxyindole-2-carboxamide Chemical compound C1CN(C)CCN1C1=CC(OC=2C=3N(C)C(C(=O)NC=4C(=CN=C(C=4)C(C)(C)C)S(C)=O)=CC=3C=CC=2)=CC=N1 RGEHOVSPXMOFJS-UHFFFAOYSA-N 0.000 claims 1
- FTPSXZOTFCPGEY-UHFFFAOYSA-N n-(5-tert-butyl-2-methylpyridin-3-yl)-1-methyl-7-[2-(4-methylpiperazin-1-yl)pyridin-4-yl]oxyindole-2-carboxamide Chemical compound C1CN(C)CCN1C1=CC(OC=2C=3N(C)C(C(=O)NC=4C(=NC=C(C=4)C(C)(C)C)C)=CC=3C=CC=2)=CC=N1 FTPSXZOTFCPGEY-UHFFFAOYSA-N 0.000 claims 1
- JGBCDDNLVNNVDP-UHFFFAOYSA-N n-(5-tert-butyl-2-methylpyridin-3-yl)-1-methyl-7-[2-(4-methylpiperazin-1-yl)pyrimidin-4-yl]oxyindole-2-carboxamide Chemical compound C1CN(C)CCN1C1=NC=CC(OC=2C=3N(C)C(C(=O)NC=4C(=NC=C(C=4)C(C)(C)C)C)=CC=3C=CC=2)=N1 JGBCDDNLVNNVDP-UHFFFAOYSA-N 0.000 claims 1
- VHPRXLOYYSAIRC-UHFFFAOYSA-N n-(5-tert-butyl-3-cyano-2-methoxyphenyl)-1-methyl-7-[2-(4-methylpiperazin-1-yl)pyridin-4-yl]oxyindole-2-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(C#N)C(OC)=C1NC(=O)C1=CC2=CC=CC(OC=3C=C(N=CC=3)N3CCN(C)CC3)=C2N1C VHPRXLOYYSAIRC-UHFFFAOYSA-N 0.000 claims 1
- CWWSWNHORYIAPS-UHFFFAOYSA-N n-(5-tert-butyl-3-cyano-2-methoxyphenyl)-1-methyl-7-[2-(4-methylpiperazin-1-yl)pyrimidin-4-yl]oxyindole-2-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(C#N)C(OC)=C1NC(=O)C1=CC2=CC=CC(OC=3N=C(N=CC=3)N3CCN(C)CC3)=C2N1C CWWSWNHORYIAPS-UHFFFAOYSA-N 0.000 claims 1
- KZPVENRWOMYPGP-UHFFFAOYSA-N n-(5-tert-butyl-3-cyano-2-methoxyphenyl)-1-methyl-7-pyridin-4-yloxyindole-2-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(C#N)C(OC)=C1NC(=O)C1=CC2=CC=CC(OC=3C=CN=CC=3)=C2N1C KZPVENRWOMYPGP-UHFFFAOYSA-N 0.000 claims 1
- BXBOQEWXJKZESY-UHFFFAOYSA-N n-[3-(methanesulfonamido)-2-methoxy-5-(1-methylcyclopropyl)phenyl]-1-methyl-7-[2-(4-methylpiperazin-1-yl)pyridin-4-yl]oxyindole-2-carboxamide Chemical compound C1=C(C2(C)CC2)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C(N(C1=2)C)=CC1=CC=CC=2OC(C=1)=CC=NC=1N1CCN(C)CC1 BXBOQEWXJKZESY-UHFFFAOYSA-N 0.000 claims 1
- PXQNKJOHICMOCU-UHFFFAOYSA-N n-[6-tert-butyl-2-(methanesulfonamido)-3-methoxypyridin-4-yl]-1-methyl-7-[2-(4-methylpiperazin-1-yl)pyridin-4-yl]oxyindole-2-carboxamide Chemical compound C1=C(C(C)(C)C)N=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC2=CC=CC(OC=3C=C(N=CC=3)N3CCN(C)CC3)=C2N1C PXQNKJOHICMOCU-UHFFFAOYSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 135
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 111
- 239000000243 solution Substances 0.000 description 99
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 38
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- ONDSBJMLAHVLMI-UHFFFAOYSA-N trimethylsilyldiazomethane Chemical compound C[Si](C)(C)[CH-][N+]#N ONDSBJMLAHVLMI-UHFFFAOYSA-N 0.000 description 8
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- C—CHEMISTRY; METALLURGY
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- 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
- C07D401/02—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 two hetero rings
- C07D401/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
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| US56769304P | 2004-05-03 | 2004-05-03 | |
| US60/567,693 | 2004-05-03 | ||
| PCT/US2005/014947 WO2005108387A2 (en) | 2004-05-03 | 2005-04-29 | Cytokine inhibitors |
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| JP2007536231A JP2007536231A (ja) | 2007-12-13 |
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| US7531560B2 (en) * | 2004-11-10 | 2009-05-12 | Boehringer Ingelheim Pharmaceuticals, Inc. | Anti-cytokine heterocyclic compounds |
| WO2007056016A2 (en) * | 2005-11-02 | 2007-05-18 | Kemia, Inc. | Bisamide cytokine inhibitors |
| WO2007067444A1 (en) * | 2005-12-08 | 2007-06-14 | Millennium Pharmaceuticals, Inc. | Bicyclic compounds with kinase inhibitory activity |
| WO2010088195A1 (en) | 2009-01-30 | 2010-08-05 | Boehringer Ingelheim International Gmbh | Azaquinazolinediones useful as chymase inhibitors |
| US9630896B2 (en) | 2013-11-22 | 2017-04-25 | Tansna Therapeutics, Inc. | 2,5-dialkyl-4-H/halo/ether-phenol compounds |
| MY195016A (en) | 2014-08-04 | 2023-01-03 | Nuevolution As | Optionally Fused Heterocyclyl-Substituted Derivatives of Pyrimidine Useful for The Treatment of Inflammatory, Metabolic, Oncologic and Autoimmune Diseases |
| US20170107216A1 (en) | 2015-10-19 | 2017-04-20 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| MD3377488T2 (ro) | 2015-11-19 | 2023-02-28 | Incyte Corp | Compuși heterociclici ca imunomodulatori |
| ES2916874T3 (es) | 2015-12-17 | 2022-07-06 | Incyte Corp | Derivados de N-fenil-piridina-2-carboxamida y su uso como moduladores de la interacción proteína/proteína PD-1/PD-L1 |
| CA3009474A1 (en) | 2015-12-22 | 2017-06-29 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| ES2906460T3 (es) | 2016-05-06 | 2022-04-18 | Incyte Corp | Compuestos heterocíclicos como inmunomoduladores |
| EP3464279B1 (en) | 2016-05-26 | 2021-11-24 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| KR102218333B1 (ko) | 2016-06-07 | 2021-02-22 | 자코바이오 파마슈티칼스 컴퍼니 리미티드 | Shp2 억제제로서 유용한 신규한 헤테로환형 유도체 |
| SG11201811414TA (en) | 2016-06-20 | 2019-01-30 | Incyte Corp | Heterocyclic compounds as immunomodulators |
| MA45669A (fr) | 2016-07-14 | 2019-05-22 | Incyte Corp | Composés hétérocycliques utilisés comme immunomodulateurs |
| US20180057486A1 (en) | 2016-08-29 | 2018-03-01 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| WO2018042352A1 (en) * | 2016-08-31 | 2018-03-08 | Taro Pharmaceutical Industries | Fenoldopam topical formulations for treating skin disorders |
| WO2018119221A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Pyridine derivatives as immunomodulators |
| EP4223369A1 (en) | 2016-12-22 | 2023-08-09 | Incyte Corporation | Immunomodulator compounds and methods of use |
| WO2018119286A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Bicyclic heteroaromatic compounds as immunomodulators |
| US10308644B2 (en) | 2016-12-22 | 2019-06-04 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| WO2018119236A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Triazolo[1,5-a]pyridine derivatives as immunomodulators |
| SG11201908820VA (en) | 2017-03-23 | 2019-10-30 | Jacobio Pharmaceuticals Co Ltd | Novel heterocyclic derivatives useful as shp2 inhibitors |
| US10364245B2 (en) | 2017-06-07 | 2019-07-30 | Chiesi Farmaceutici S.P.A. | Kinase inhibitors |
| SMT202300065T1 (it) | 2018-03-30 | 2023-05-12 | Incyte Corp | Composti eterociclici come immunomodulatori |
| CN112752756B (zh) | 2018-05-11 | 2024-06-25 | 因赛特公司 | 作为PD-L1免疫调节剂的四氢-咪唑并[4,5-c]吡啶衍生物 |
| CN112839935A (zh) | 2018-09-26 | 2021-05-25 | 北京加科思新药研发有限公司 | 可用作shp2抑制剂的新型杂环衍生物 |
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| JP7559059B2 (ja) | 2019-09-30 | 2024-10-01 | インサイト・コーポレイション | 免疫調節剤としてのピリド［３，２－ｄ］ピリミジン化合物 |
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| AU2020405446A1 (en) | 2019-12-20 | 2022-05-26 | Nuevolution A/S | Compounds active towards nuclear receptors |
| BR112022012205A2 (pt) | 2019-12-20 | 2022-09-13 | Nuevolution As | Compostos ativos para receptores nucleares |
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| CA3174252A1 (en) | 2020-03-31 | 2021-10-07 | Nuevolution A/S | Compounds active towards nuclear receptors |
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- 2005-04-29 JP JP2007511450A patent/JP4865702B2/ja not_active Expired - Fee Related
- 2005-04-29 CA CA2560387A patent/CA2560387C/en not_active Expired - Fee Related
- 2005-04-29 EP EP05745042A patent/EP1745036A2/en not_active Withdrawn
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| WO2003087085A1 (en) * | 2002-04-11 | 2003-10-23 | Boehringer Ingelheim Pharmaceuticals, Inc. | Heterocyclic amide derivatives as cytokine inhibitors |
Also Published As
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| EP1745036A2 (en) | 2007-01-24 |
| JP2007536231A (ja) | 2007-12-13 |
| US20070275946A1 (en) | 2007-11-29 |
| US20090023701A1 (en) | 2009-01-22 |
| US20050245536A1 (en) | 2005-11-03 |
| WO2005108387A2 (en) | 2005-11-17 |
| CA2560387C (en) | 2013-09-24 |
| US7592332B2 (en) | 2009-09-22 |
| WO2005108387A3 (en) | 2006-02-16 |
| CA2560387A1 (en) | 2005-11-17 |
| US7285545B2 (en) | 2007-10-23 |
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