JP4237497B2 - ピラゾロピリジン類、その調製方法及びその治療用化合物としての使用 - Google Patents
ピラゾロピリジン類、その調製方法及びその治療用化合物としての使用 Download PDFInfo
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- JP4237497B2 JP4237497B2 JP2002576966A JP2002576966A JP4237497B2 JP 4237497 B2 JP4237497 B2 JP 4237497B2 JP 2002576966 A JP2002576966 A JP 2002576966A JP 2002576966 A JP2002576966 A JP 2002576966A JP 4237497 B2 JP4237497 B2 JP 4237497B2
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- Prior art keywords
- fluorophenyl
- formula
- pyrazolo
- het
- compound
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- 150000001875 compounds Chemical class 0.000 title claims description 510
- 238000002360 preparation method Methods 0.000 title description 48
- 230000001225 therapeutic effect Effects 0.000 title description 2
- 150000005229 pyrazolopyridines Chemical class 0.000 title 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 138
- 125000000217 alkyl group Chemical group 0.000 claims description 126
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 100
- 125000005843 halogen group Chemical group 0.000 claims description 89
- 125000003342 alkenyl group Chemical group 0.000 claims description 83
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 71
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 52
- 125000003118 aryl group Chemical group 0.000 claims description 51
- 125000001072 heteroaryl group Chemical group 0.000 claims description 43
- 150000003839 salts Chemical class 0.000 claims description 41
- 125000000304 alkynyl group Chemical group 0.000 claims description 37
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 36
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 35
- 125000004429 atom Chemical group 0.000 claims description 35
- 208000029433 Herpesviridae infectious disease Diseases 0.000 claims description 34
- 239000012453 solvate Substances 0.000 claims description 30
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 27
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims description 26
- 241001465754 Metazoa Species 0.000 claims description 23
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 22
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 19
- 125000005842 heteroatom Chemical group 0.000 claims description 17
- 125000004791 2-fluoroethoxy group Chemical group FCCO* 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 13
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 12
- 150000001540 azides Chemical class 0.000 claims description 7
- VCPKBMGKZBUKBH-UHFFFAOYSA-N ethyl 3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)-7-methylpyrazolo[1,5-a]pyridine-6-carboxylate Chemical compound N=1N2C(C)=C(C(=O)OCC)C=CC2=C(C=2N=C(NC3CCCC3)N=CC=2)C=1C1=CC=C(F)C=C1 VCPKBMGKZBUKBH-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- FWOSJJUOEZEDIL-UHFFFAOYSA-N 2-(4-fluorophenyl)-7-methylsulfanyl-3-pyrimidin-4-ylpyrazolo[1,5-a]pyridine Chemical compound N=1N2C(SC)=CC=CC2=C(C=2N=CN=CC=2)C=1C1=CC=C(F)C=C1 FWOSJJUOEZEDIL-UHFFFAOYSA-N 0.000 claims description 5
- VKWBLQPHYOLIAC-UHFFFAOYSA-N 2-(4-fluorophenyl)-3-(2-fluoropyridin-4-yl)-7-methoxypyrazolo[1,5-a]pyridine Chemical compound N=1N2C(OC)=CC=CC2=C(C=2C=C(F)N=CC=2)C=1C1=CC=C(F)C=C1 VKWBLQPHYOLIAC-UHFFFAOYSA-N 0.000 claims description 4
- CPWDRPDDVGWEFF-UHFFFAOYSA-N 3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)-7-methylpyrazolo[1,5-a]pyridine-6-carboxylic acid Chemical compound N=1N2C(C)=C(C(O)=O)C=CC2=C(C=2N=C(NC3CCCC3)N=CC=2)C=1C1=CC=C(F)C=C1 CPWDRPDDVGWEFF-UHFFFAOYSA-N 0.000 claims description 4
- ALUNYQHYRPHVIL-UHFFFAOYSA-N 4-[5-chloro-7-ethylsulfanyl-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]-n-cyclopentylpyrimidin-2-amine Chemical compound N=1N2C(SCC)=CC(Cl)=CC2=C(C=2N=C(NC3CCCC3)N=CC=2)C=1C1=CC=C(F)C=C1 ALUNYQHYRPHVIL-UHFFFAOYSA-N 0.000 claims description 4
- AAAWHWUDFGBWLM-UHFFFAOYSA-N n-butyl-4-[7-butyl-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound CCCCNC1=NC=CC(C2=C3C=CC=C(CCCC)N3N=C2C=2C=CC(F)=CC=2)=N1 AAAWHWUDFGBWLM-UHFFFAOYSA-N 0.000 claims description 4
- KWZAQIPJIJEAHE-UHFFFAOYSA-N 2-(4-fluorophenyl)-7-methyl-3-pyrimidin-4-ylpyrazolo[1,5-a]pyridine Chemical compound N=1N2C(C)=CC=CC2=C(C=2N=CN=CC=2)C=1C1=CC=C(F)C=C1 KWZAQIPJIJEAHE-UHFFFAOYSA-N 0.000 claims description 3
- MFMOOUJNQJMODJ-UHFFFAOYSA-N 2-(4-fluorophenyl)-7-methylsulfinyl-3-pyrimidin-4-ylpyrazolo[1,5-a]pyridine Chemical compound N=1N2C(S(=O)C)=CC=CC2=C(C=2N=CN=CC=2)C=1C1=CC=C(F)C=C1 MFMOOUJNQJMODJ-UHFFFAOYSA-N 0.000 claims description 3
- FSHHBWRYYGOFON-UHFFFAOYSA-N 3-[2-(cyclopentylamino)pyrimidin-4-yl]-n-cyclopropyl-2-(4-fluorophenyl)-7-methylpyrazolo[1,5-a]pyridine-6-carboxamide Chemical compound N=1N2C(C)=C(C(=O)NC3CC3)C=CC2=C(C=2N=C(NC3CCCC3)N=CC=2)C=1C1=CC=C(F)C=C1 FSHHBWRYYGOFON-UHFFFAOYSA-N 0.000 claims description 3
- FSWUERNXFMGBLY-UHFFFAOYSA-N n-butyl-4-[2-(4-fluorophenyl)-7-methoxypyrazolo[1,5-a]pyridin-3-yl]pyridin-2-amine Chemical compound C1=NC(NCCCC)=CC(C2=C3C=CC=C(OC)N3N=C2C=2C=CC(F)=CC=2)=C1 FSWUERNXFMGBLY-UHFFFAOYSA-N 0.000 claims description 3
- ICZGXQDFRHTYAC-UHFFFAOYSA-N n-butyl-4-[2-(4-fluorophenyl)-7-methylpyrazolo[1,5-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound CCCCNC1=NC=CC(C2=C3C=CC=C(C)N3N=C2C=2C=CC(F)=CC=2)=N1 ICZGXQDFRHTYAC-UHFFFAOYSA-N 0.000 claims description 3
- UJNAJQWXFFGKKX-UHFFFAOYSA-N n-butyl-4-[2-(4-fluorophenyl)-7-octylpyrazolo[1,5-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound N=1N2C(CCCCCCCC)=CC=CC2=C(C=2N=C(NCCCC)N=CC=2)C=1C1=CC=C(F)C=C1 UJNAJQWXFFGKKX-UHFFFAOYSA-N 0.000 claims description 3
- DATUUAWYIBTSAP-UHFFFAOYSA-N 4-[5-chloro-2-(3-chlorophenyl)-7-methylsulfanylpyrazolo[1,5-a]pyridin-3-yl]-n-cyclopentylpyrimidin-2-amine Chemical compound N=1N2C(SC)=CC(Cl)=CC2=C(C=2N=C(NC3CCCC3)N=CC=2)C=1C1=CC=CC(Cl)=C1 DATUUAWYIBTSAP-UHFFFAOYSA-N 0.000 claims description 2
- CYWPJXJQYLJJJU-UHFFFAOYSA-N 2-(4-fluorophenyl)-7-methoxy-3-pyridin-4-ylpyrazolo[1,5-a]pyridine Chemical compound N=1N2C(OC)=CC=CC2=C(C=2C=CN=CC=2)C=1C1=CC=C(F)C=C1 CYWPJXJQYLJJJU-UHFFFAOYSA-N 0.000 claims 1
- TULDMBUASKXWQC-UHFFFAOYSA-N 2-(4-fluorophenyl)-7-methyl-3-pyridin-4-ylpyrazolo[1,5-a]pyridine Chemical compound N=1N2C(C)=CC=CC2=C(C=2C=CN=CC=2)C=1C1=CC=C(F)C=C1 TULDMBUASKXWQC-UHFFFAOYSA-N 0.000 claims 1
- QNVKXLSVONAZKV-UHFFFAOYSA-N 3-[[4-[2-(4-fluorophenyl)-7-(2,2,2-trifluoroethoxy)pyrazolo[1,5-a]pyridin-3-yl]pyrimidin-2-yl]amino]propan-1-ol Chemical compound OCCCNC1=NC=CC(C2=C3C=CC=C(OCC(F)(F)F)N3N=C2C=2C=CC(F)=CC=2)=N1 QNVKXLSVONAZKV-UHFFFAOYSA-N 0.000 claims 1
- LLYOXXZRADCLIG-UHFFFAOYSA-N 4-[7-butoxy-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl]-n-cyclopentylpyrimidin-2-amine Chemical compound N=1N2C(OCCCC)=CC=CC2=C(C=2N=C(NC3CCCC3)N=CC=2)C=1C1=CC=C(OC)C=C1 LLYOXXZRADCLIG-UHFFFAOYSA-N 0.000 claims 1
- YCSRTLSCIFUTIR-UHFFFAOYSA-N N=1N2C(C(=O)N(C)C)=CC=CC2=C(C=2N=C(NC3CC3)C=CN=2)C=1C1=CC=C(F)C=C1 Chemical compound N=1N2C(C(=O)N(C)C)=CC=CC2=C(C=2N=C(NC3CC3)C=CN=2)C=1C1=CC=C(F)C=C1 YCSRTLSCIFUTIR-UHFFFAOYSA-N 0.000 claims 1
- LNAFZJTYZROKMK-UHFFFAOYSA-N n-benzyl-4-[2-(4-fluorophenyl)-7-(2,2,2-trifluoroethoxy)pyrazolo[1,5-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound C1=CC(F)=CC=C1C1=NN(C(OCC(F)(F)F)=CC=C2)C2=C1C1=CC=NC(NCC=2C=CC=CC=2)=N1 LNAFZJTYZROKMK-UHFFFAOYSA-N 0.000 claims 1
- HJMANSMLBPWXNZ-UHFFFAOYSA-N n-benzyl-4-[7-(2-fluoroethoxy)-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound N=1N2C(OCCF)=CC=CC2=C(C=2N=C(NCC=3C=CC=CC=3)N=CC=2)C=1C1=CC=C(F)C=C1 HJMANSMLBPWXNZ-UHFFFAOYSA-N 0.000 claims 1
- YWDVFVLTQJXIBQ-UHFFFAOYSA-N n-butyl-4-[2-(4-fluorophenyl)-7-(2,2,2-trifluoroethoxy)pyrazolo[1,5-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound CCCCNC1=NC=CC(C2=C3C=CC=C(OCC(F)(F)F)N3N=C2C=2C=CC(F)=CC=2)=N1 YWDVFVLTQJXIBQ-UHFFFAOYSA-N 0.000 claims 1
- GFANAAWSJNBJLM-UHFFFAOYSA-N n-butyl-4-[7-(2-fluoroethoxy)-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound CCCCNC1=NC=CC(C2=C3C=CC=C(OCCF)N3N=C2C=2C=CC(F)=CC=2)=N1 GFANAAWSJNBJLM-UHFFFAOYSA-N 0.000 claims 1
- YTJPNPRRZYFARD-UHFFFAOYSA-N n-cyclohexyl-4-[2-(4-fluorophenyl)-7-(2,2,2-trifluoroethoxy)pyrazolo[1,5-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound C1=CC(F)=CC=C1C1=NN(C(OCC(F)(F)F)=CC=C2)C2=C1C1=CC=NC(NC2CCCCC2)=N1 YTJPNPRRZYFARD-UHFFFAOYSA-N 0.000 claims 1
- MXLAFDQBEKLLLP-UHFFFAOYSA-N n-cyclopentyl-4-[2-(4-fluorophenyl)-5-morpholin-4-yl-7-propan-2-ylsulfanylpyrazolo[1,5-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound N=1N2C(SC(C)C)=CC(N3CCOCC3)=CC2=C(C=2N=C(NC3CCCC3)N=CC=2)C=1C1=CC=C(F)C=C1 MXLAFDQBEKLLLP-UHFFFAOYSA-N 0.000 claims 1
- NIGAGTQHKWHZTA-UHFFFAOYSA-N n-cyclopentyl-4-[2-(4-fluorophenyl)-7-(2,2,2-trifluoroethoxy)pyrazolo[1,5-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound C1=CC(F)=CC=C1C1=NN(C(OCC(F)(F)F)=CC=C2)C2=C1C1=CC=NC(NC2CCCC2)=N1 NIGAGTQHKWHZTA-UHFFFAOYSA-N 0.000 claims 1
- NMMWASSQZHYMCO-UHFFFAOYSA-N n-cyclopentyl-4-[2-(4-fluorophenyl)-7-methylsulfanyl-5-morpholin-4-ylpyrazolo[1,5-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound N=1N2C(SC)=CC(N3CCOCC3)=CC2=C(C=2N=C(NC3CCCC3)N=CC=2)C=1C1=CC=C(F)C=C1 NMMWASSQZHYMCO-UHFFFAOYSA-N 0.000 claims 1
- KLRJIYIAXBHQAR-UHFFFAOYSA-N n-cyclopentyl-6-[2-(4-fluorophenyl)-7-methylsulfanylpyrazolo[1,5-a]pyridin-3-yl]pyrimidin-4-amine Chemical compound N=1N2C(SC)=CC=CC2=C(C=2N=CN=C(NC3CCCC3)C=2)C=1C1=CC=C(F)C=C1 KLRJIYIAXBHQAR-UHFFFAOYSA-N 0.000 claims 1
- PJTIATJYIGXDQR-UHFFFAOYSA-N n-cyclopropyl-4-[2-(4-fluorophenyl)-7-(2,2,2-trifluoroethoxy)pyrazolo[1,5-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound C1=CC(F)=CC=C1C1=NN(C(OCC(F)(F)F)=CC=C2)C2=C1C1=CC=NC(NC2CC2)=N1 PJTIATJYIGXDQR-UHFFFAOYSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 183
- 238000000034 method Methods 0.000 description 124
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 123
- 239000000243 solution Substances 0.000 description 115
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 111
- 238000006243 chemical reaction Methods 0.000 description 103
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- -1 methylene, ethylene, propylene, butylene, isobutylene Chemical group 0.000 description 58
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- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
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- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
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- 229940095064 tartrate Drugs 0.000 description 1
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- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
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- XSROQCDVUIHRSI-UHFFFAOYSA-N thietane Chemical compound C1CSC1 XSROQCDVUIHRSI-UHFFFAOYSA-N 0.000 description 1
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- UNEPXPMBVGDXGH-UHFFFAOYSA-N tributyl(pyridin-4-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=NC=C1 UNEPXPMBVGDXGH-UHFFFAOYSA-N 0.000 description 1
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biotechnology (AREA)
- Medicinal Chemistry (AREA)
- Communicable Diseases (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (5)
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| US28004701P | 2001-03-30 | 2001-03-30 | |
| US30718901P | 2001-07-23 | 2001-07-23 | |
| US30778601P | 2001-07-25 | 2001-07-25 | |
| US31509001P | 2001-08-27 | 2001-08-27 | |
| PCT/US2002/008524 WO2002078700A1 (en) | 2001-03-30 | 2002-03-20 | Pyralopyridines, process for their preparation and use as therapteutic compounds |
Publications (3)
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|---|---|
| JP2004525149A JP2004525149A (ja) | 2004-08-19 |
| JP2004525149A5 JP2004525149A5 (enExample) | 2005-07-21 |
| JP4237497B2 true JP4237497B2 (ja) | 2009-03-11 |
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| JP2002576966A Expired - Fee Related JP4237497B2 (ja) | 2001-03-30 | 2002-03-20 | ピラゾロピリジン類、その調製方法及びその治療用化合物としての使用 |
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| US (2) | US7034030B2 (enExample) |
| EP (1) | EP1372643A1 (enExample) |
| JP (1) | JP4237497B2 (enExample) |
| WO (1) | WO2002078700A1 (enExample) |
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| JP4219171B2 (ja) * | 2001-04-10 | 2009-02-04 | スミスクライン ビーチャム コーポレーション | 抗ウイルス性ピラゾロピリジン化合物 |
| WO2003050120A1 (en) * | 2001-12-11 | 2003-06-19 | Smithkline Beecham Corporation | Pyrazolo-pyridine derivatives as antiherpes agents |
| ATE302203T1 (de) | 2002-03-07 | 2005-09-15 | Smithkline Beecham Corp | Pyrazolopyrimidin- und pyrazolotriazinderivate und diese enthaltende pharmazeutische zubereitungen |
| WO2004033454A1 (en) * | 2002-10-03 | 2004-04-22 | Smithkline Beecham Corporation | Therapeutic compounds based on pyrazolopyridine derivatives |
| US20070155738A1 (en) * | 2005-05-20 | 2007-07-05 | Alantos Pharmaceuticals, Inc. | Heterobicyclic metalloprotease inhibitors |
| JP5463034B2 (ja) * | 2005-05-20 | 2014-04-09 | アラントス・フアーマシユーテイカルズ・ホールデイング・インコーポレイテツド | ピリミジン若しくはトリアジン縮合二環式メタロプロテアーゼ阻害薬 |
| UA103319C2 (en) | 2008-05-06 | 2013-10-10 | Глаксосмитклайн Ллк | Thiazole- and oxazole-benzene sulfonamide compounds |
| PE20120325A1 (es) * | 2009-05-19 | 2012-04-12 | Dow Agrosciences Llc | Aminopirimidinas sustituidas con arilo como agentes fungicidas |
| US20110039873A1 (en) * | 2009-06-08 | 2011-02-17 | Gaeta Federico C A | SUBSTITUTED PYRAZOLO[1,5-a] PYRIDINE COMPOUNDS HAVING MULTI-TARGET ACTIVITY |
| EP2448938B9 (en) | 2009-06-29 | 2015-06-10 | Incyte Corporation | Pyrimidinones as pi3k inhibitors |
| WO2011075643A1 (en) * | 2009-12-18 | 2011-06-23 | Incyte Corporation | Substituted heteroaryl fused derivatives as pi3k inhibitors |
| WO2011075630A1 (en) * | 2009-12-18 | 2011-06-23 | Incyte Corporation | Substituted fused aryl and heteroaryl derivatives as pi3k inhibitors |
| EP2558463A1 (en) | 2010-04-14 | 2013-02-20 | Incyte Corporation | Fused derivatives as i3 inhibitors |
| US9062055B2 (en) | 2010-06-21 | 2015-06-23 | Incyte Corporation | Fused pyrrole derivatives as PI3K inhibitors |
| EP2402335A1 (en) | 2010-06-29 | 2012-01-04 | Basf Se | Pyrazolopyridine compounds |
| EP2402336A1 (en) | 2010-06-29 | 2012-01-04 | Basf Se | Pyrazolopyridine compounds |
| JP5961187B2 (ja) | 2010-12-20 | 2016-08-02 | インサイト・ホールディングス・コーポレイションＩｎｃｙｔｅ Ｈｏｌｄｉｎｇｓ Ｃｏｒｐｏｒａｔｉｏｎ | Ｐｉ３ｋ阻害剤としてのｎ−（１−（置換フェニル）エチル）−９ｈ−プリン−６−アミン |
| US9108984B2 (en) | 2011-03-14 | 2015-08-18 | Incyte Corporation | Substituted diamino-pyrimidine and diamino-pyridine derivatives as PI3K inhibitors |
| US9126948B2 (en) | 2011-03-25 | 2015-09-08 | Incyte Holdings Corporation | Pyrimidine-4,6-diamine derivatives as PI3K inhibitors |
| MX389479B (es) | 2011-09-02 | 2025-03-20 | Incyte Holdings Corp | Heterociclilaminas como inhibidores de fosfoinositida 3-cinasas (pi3k) |
| AR090548A1 (es) | 2012-04-02 | 2014-11-19 | Incyte Corp | Azaheterociclobencilaminas biciclicas como inhibidores de pi3k |
| US10077277B2 (en) | 2014-06-11 | 2018-09-18 | Incyte Corporation | Bicyclic heteroarylaminoalkyl phenyl derivatives as PI3K inhibitors |
| BR112017003745A2 (pt) | 2014-08-29 | 2017-12-05 | Tes Pharma S R L | inibidores de semialdeído descarboxilase de ácido alfa-amino-beta-carboximucônico |
| SG10201912302VA (en) | 2015-02-27 | 2020-02-27 | Incyte Corp | Salts of pi3k inhibitor and processes for their preparation |
| WO2016183060A1 (en) | 2015-05-11 | 2016-11-17 | Incyte Corporation | Process for the synthesis of a phosphoinositide 3-kinase inhibitor |
| US9988401B2 (en) | 2015-05-11 | 2018-06-05 | Incyte Corporation | Crystalline forms of a PI3K inhibitor |
| 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 |
| 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 |
| WO2018119236A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Triazolo[1,5-a]pyridine derivatives as immunomodulators |
| EP4223369A1 (en) | 2016-12-22 | 2023-08-09 | Incyte Corporation | Immunomodulator compounds and methods of use |
| US10308644B2 (en) | 2016-12-22 | 2019-06-04 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| WO2018119221A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Pyridine derivatives as immunomodulators |
| WO2018119286A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Bicyclic heteroaromatic compounds as immunomodulators |
| 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 |
| IL278889B2 (en) | 2018-06-01 | 2025-11-01 | Incyte Corp | Dosing regimen for the treatment of pi3k related disorders |
| US11066404B2 (en) | 2018-10-11 | 2021-07-20 | Incyte Corporation | Dihydropyrido[2,3-d]pyrimidinone compounds as CDK2 inhibitors |
| WO2020168197A1 (en) | 2019-02-15 | 2020-08-20 | Incyte Corporation | Pyrrolo[2,3-d]pyrimidinone compounds as cdk2 inhibitors |
| TW202100520A (zh) | 2019-03-05 | 2021-01-01 | 美商英塞特公司 | 作為cdk2 抑制劑之吡唑基嘧啶基胺化合物 |
| US11919904B2 (en) | 2019-03-29 | 2024-03-05 | Incyte Corporation | Sulfonylamide compounds as CDK2 inhibitors |
| WO2020223558A1 (en) | 2019-05-01 | 2020-11-05 | Incyte Corporation | Tricyclic amine compounds as cdk2 inhibitors |
| WO2020223469A1 (en) | 2019-05-01 | 2020-11-05 | Incyte Corporation | N-(1-(methylsulfonyl)piperidin-4-yl)-4,5-di hydro-1h-imidazo[4,5-h]quinazolin-8-amine derivatives and related compounds as cyclin-dependent kinase 2 (cdk2) inhibitors for treating cancer |
| TW202115059A (zh) | 2019-08-09 | 2021-04-16 | 美商英塞特公司 | Ｐｄ—１／ｐｄ—ｌ１抑制劑之鹽 |
| WO2021030537A1 (en) | 2019-08-14 | 2021-02-18 | Incyte Corporation | Imidazolyl pyrimidinylamine compounds as cdk2 inhibitors |
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2002
- 2002-03-20 EP EP02733866A patent/EP1372643A1/en not_active Withdrawn
- 2002-03-20 JP JP2002576966A patent/JP4237497B2/ja not_active Expired - Fee Related
- 2002-03-20 WO PCT/US2002/008524 patent/WO2002078700A1/en not_active Ceased
- 2002-03-20 US US10/473,196 patent/US7034030B2/en not_active Expired - Fee Related
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2005
- 2005-10-07 US US11/245,972 patent/US7109209B2/en not_active Expired - Fee Related
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|---|---|
| US7034030B2 (en) | 2006-04-25 |
| US7109209B2 (en) | 2006-09-19 |
| JP2004525149A (ja) | 2004-08-19 |
| US20050059677A1 (en) | 2005-03-17 |
| WO2002078700A1 (en) | 2002-10-10 |
| US20060058319A1 (en) | 2006-03-16 |
| EP1372643A1 (en) | 2004-01-02 |
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