JP4219171B2 - 抗ウイルス性ピラゾロピリジン化合物 - Google Patents
抗ウイルス性ピラゾロピリジン化合物 Download PDFInfo
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- JP4219171B2 JP4219171B2 JP2002581427A JP2002581427A JP4219171B2 JP 4219171 B2 JP4219171 B2 JP 4219171B2 JP 2002581427 A JP2002581427 A JP 2002581427A JP 2002581427 A JP2002581427 A JP 2002581427A JP 4219171 B2 JP4219171 B2 JP 4219171B2
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- cycloalkyl
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- 230000000840 anti-viral effect Effects 0.000 title description 3
- 150000005229 pyrazolopyridines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 636
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 16
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 280
- 125000000217 alkyl group Chemical group 0.000 claims description 153
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 131
- 125000003342 alkenyl group Chemical group 0.000 claims description 108
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 90
- 125000005843 halogen group Chemical group 0.000 claims description 84
- 125000003118 aryl group Chemical group 0.000 claims description 57
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 51
- 125000004429 atom Chemical group 0.000 claims description 49
- 125000001072 heteroaryl group Chemical group 0.000 claims description 43
- 125000000304 alkynyl group Chemical group 0.000 claims description 41
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 40
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims description 36
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 35
- 150000003839 salts Chemical class 0.000 claims description 30
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 29
- 208000029433 Herpesviridae infectious disease Diseases 0.000 claims description 27
- 125000005842 heteroatom Chemical group 0.000 claims description 26
- 230000002265 prevention Effects 0.000 claims description 26
- 241001465754 Metazoa Species 0.000 claims description 24
- 239000012453 solvate Substances 0.000 claims description 21
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 19
- 150000001540 azides Chemical class 0.000 claims description 19
- NUKYEHFDVLNGFZ-UHFFFAOYSA-N 4-[5-(cyclopentylamino)-3-[2-(cyclopentylamino)pyrimidin-4-yl]pyrazolo[1,5-a]pyridin-2-yl]phenol Chemical compound C1=CC(O)=CC=C1C1=NN(C=CC(NC2CCCC2)=C2)C2=C1C1=CC=NC(NC2CCCC2)=N1 NUKYEHFDVLNGFZ-UHFFFAOYSA-N 0.000 claims description 6
- SQQVANPMGGBYDX-UHFFFAOYSA-N n-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-5-amine Chemical compound C1=CC(F)=CC=C1C1=NN(C=CC(NC2CCCC2)=C2)C2=C1C1=CC=NC(NC2CCCC2)=N1 SQQVANPMGGBYDX-UHFFFAOYSA-N 0.000 claims description 6
- URUUOQUMOPTRRE-UHFFFAOYSA-N n-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-5-amine Chemical compound C1=CC(OC)=CC=C1C1=NN(C=CC(NC2CCCC2)=C2)C2=C1C1=CC=NC(NC2CCCC2)=N1 URUUOQUMOPTRRE-UHFFFAOYSA-N 0.000 claims description 6
- OUZIVEFGDDPQGR-UHFFFAOYSA-N 3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-5-amine Chemical compound C=12C=C(N)C=CN2N=C(C=2C=CC(F)=CC=2)C=1C(N=1)=CC=NC=1NC1CCCC1 OUZIVEFGDDPQGR-UHFFFAOYSA-N 0.000 claims description 5
- NLKACQGBKCKERK-UHFFFAOYSA-N n-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-[4-(2-methylpropoxy)phenyl]pyrazolo[1,5-a]pyridin-5-amine Chemical compound C1=CC(OCC(C)C)=CC=C1C1=NN(C=CC(NC2CCCC2)=C2)C2=C1C1=CC=NC(NC2CCCC2)=N1 NLKACQGBKCKERK-UHFFFAOYSA-N 0.000 claims description 5
- GBVRWXQLLMGEQJ-UHFFFAOYSA-N n-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-[4-(cyclopropylmethoxy)phenyl]pyrazolo[1,5-a]pyridin-5-amine Chemical compound C1CC1COC(C=C1)=CC=C1C(C(=C1C=2)C=3N=C(NC4CCCC4)N=CC=3)=NN1C=CC=2NC1CCCC1 GBVRWXQLLMGEQJ-UHFFFAOYSA-N 0.000 claims description 5
- FPZNHXIUFKJEHG-UHFFFAOYSA-N 3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)-n-(2-methoxyethyl)pyrazolo[1,5-a]pyridin-5-amine Chemical compound C=12C=C(NCCOC)C=CN2N=C(C=2C=CC(F)=CC=2)C=1C(N=1)=CC=NC=1NC1CCCC1 FPZNHXIUFKJEHG-UHFFFAOYSA-N 0.000 claims description 4
- ZBASGXKVNVIJCM-UHFFFAOYSA-N 3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)-n-propan-2-ylpyrazolo[1,5-a]pyridin-6-amine Chemical compound N=1N2C=C(NC(C)C)C=CC2=C(C=2N=C(NC3CCCC3)N=CC=2)C=1C1=CC=C(F)C=C1 ZBASGXKVNVIJCM-UHFFFAOYSA-N 0.000 claims description 4
- FEIKULOVKMOBGQ-UHFFFAOYSA-N 3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-6-amine Chemical compound N=1N2C=C(N)C=CC2=C(C=2N=C(NC3CCCC3)N=CC=2)C=1C1=CC=C(F)C=C1 FEIKULOVKMOBGQ-UHFFFAOYSA-N 0.000 claims description 4
- RMANLZQDOIEBGU-UHFFFAOYSA-N 3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-methoxyphenyl)-n-propan-2-ylpyrazolo[1,5-a]pyridin-5-amine Chemical compound C1=CC(OC)=CC=C1C1=NN(C=CC(NC(C)C)=C2)C2=C1C1=CC=NC(NC2CCCC2)=N1 RMANLZQDOIEBGU-UHFFFAOYSA-N 0.000 claims description 4
- SQOVLUIXVMRKMK-UHFFFAOYSA-N n-[3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-5-yl]methanesulfonamide Chemical compound C=12C=C(NS(=O)(=O)C)C=CN2N=C(C=2C=CC(F)=CC=2)C=1C(N=1)=CC=NC=1NC1CCCC1 SQOVLUIXVMRKMK-UHFFFAOYSA-N 0.000 claims description 4
- XDGMTTPBMWQFBC-UHFFFAOYSA-N n-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-6-amine Chemical compound C1=CC(F)=CC=C1C1=NN(C=C(NC2CCCC2)C=C2)C2=C1C1=CC=NC(NC2CCCC2)=N1 XDGMTTPBMWQFBC-UHFFFAOYSA-N 0.000 claims description 4
- FDXDGPUMMWYVHH-UHFFFAOYSA-N 3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)-n-propan-2-ylpyrazolo[1,5-a]pyridin-5-amine Chemical compound C=12C=C(NC(C)C)C=CN2N=C(C=2C=CC(F)=CC=2)C=1C(N=1)=CC=NC=1NC1CCCC1 FDXDGPUMMWYVHH-UHFFFAOYSA-N 0.000 claims description 3
- HZRFMJKFCUASOU-UHFFFAOYSA-N 4-bromo-n-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-5-amine Chemical compound C1=CC(F)=CC=C1C1=NN(C=CC(NC2CCCC2)=C2Br)C2=C1C1=CC=NC(NC2CCCC2)=N1 HZRFMJKFCUASOU-UHFFFAOYSA-N 0.000 claims description 3
- KCKHDUBDEHXGJB-UHFFFAOYSA-N 4-bromo-n-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-5-amine Chemical compound C1=CC(OC)=CC=C1C1=NN(C=CC(NC2CCCC2)=C2Br)C2=C1C1=CC=NC(NC2CCCC2)=N1 KCKHDUBDEHXGJB-UHFFFAOYSA-N 0.000 claims description 3
- KOWHYEFJCNLWGI-UHFFFAOYSA-N 4-chloro-n-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-5-amine Chemical compound C1=CC(F)=CC=C1C1=NN(C=CC(NC2CCCC2)=C2Cl)C2=C1C1=CC=NC(NC2CCCC2)=N1 KOWHYEFJCNLWGI-UHFFFAOYSA-N 0.000 claims description 3
- WHOWUHRMZQLXRB-UHFFFAOYSA-N 4-chloro-n-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-5-amine Chemical compound C1=CC(OC)=CC=C1C1=NN(C=CC(NC2CCCC2)=C2Cl)C2=C1C1=CC=NC(NC2CCCC2)=N1 WHOWUHRMZQLXRB-UHFFFAOYSA-N 0.000 claims description 3
- LNVZHPGLGRXNAI-UHFFFAOYSA-N n-butyl-3-[2-(butylamino)pyridin-4-yl]-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-4-amine Chemical compound C1=NC(NCCCC)=CC(C2=C3C(NCCCC)=CC=CN3N=C2C=2C=CC(F)=CC=2)=C1 LNVZHPGLGRXNAI-UHFFFAOYSA-N 0.000 claims description 3
- 238000000034 method Methods 0.000 abstract description 107
- 230000008569 process Effects 0.000 abstract description 16
- 239000008177 pharmaceutical agent Substances 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 122
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 84
- 238000006243 chemical reaction Methods 0.000 description 80
- 239000000243 solution Substances 0.000 description 59
- 239000000203 mixture Substances 0.000 description 52
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- 238000005481 NMR spectroscopy Methods 0.000 description 50
- 239000002585 base Substances 0.000 description 48
- 239000007787 solid Substances 0.000 description 48
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 47
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 45
- -1 methylene, ethylene, propylene, butylene Chemical group 0.000 description 45
- 239000002904 solvent Substances 0.000 description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
- 150000001412 amines Chemical class 0.000 description 42
- 235000019439 ethyl acetate Nutrition 0.000 description 41
- 125000000623 heterocyclic group Chemical group 0.000 description 39
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 35
- 239000011541 reaction mixture Substances 0.000 description 34
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 239000003795 chemical substances by application Substances 0.000 description 28
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 28
- 238000002360 preparation method Methods 0.000 description 27
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 24
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 23
- 235000019341 magnesium sulphate Nutrition 0.000 description 23
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 23
- 201000010099 disease Diseases 0.000 description 22
- 235000019441 ethanol Nutrition 0.000 description 22
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 21
- 239000000543 intermediate Substances 0.000 description 20
- 238000001914 filtration Methods 0.000 description 18
- 238000004519 manufacturing process Methods 0.000 description 18
- 208000015181 infectious disease Diseases 0.000 description 17
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 16
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 16
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- 239000003814 drug Substances 0.000 description 15
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 15
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- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical group [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 13
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- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical group [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 12
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- 125000001424 substituent group Chemical group 0.000 description 8
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 8
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- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 description 7
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- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 7
- 238000006268 reductive amination reaction Methods 0.000 description 7
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- JFZJMSDDOOAOIV-UHFFFAOYSA-N 2-chloro-5-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=C(Cl)N=C1 JFZJMSDDOOAOIV-UHFFFAOYSA-N 0.000 description 6
- 201000006082 Chickenpox Diseases 0.000 description 6
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- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 6
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- 230000029936 alkylation Effects 0.000 description 6
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical group C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 6
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- NSGAWLOIVNMRET-UHFFFAOYSA-N tert-butyl N-[3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-6-yl]carbamate Chemical compound N=1N2C=C(NC(=O)OC(C)(C)C)C=CC2=C(C=2N=C(NC3CCCC3)N=CC=2)C=1C1=CC=C(F)C=C1 NSGAWLOIVNMRET-UHFFFAOYSA-N 0.000 description 1
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- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
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- 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
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Virology (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28274901P | 2001-04-10 | 2001-04-10 | |
| PCT/US2002/008793 WO2002083672A1 (en) | 2001-04-10 | 2002-03-21 | Antiviral pyrazolopyridine compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
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| WO2004033454A1 (en) * | 2002-10-03 | 2004-04-22 | Smithkline Beecham Corporation | Therapeutic compounds based on pyrazolopyridine derivatives |
| US7812022B2 (en) * | 2004-12-21 | 2010-10-12 | Glaxosmithkline Llc | 2-pyrimidinyl pyrazolopyridine ErbB kinase inhibitors |
| ES2421450T3 (es) * | 2005-12-05 | 2013-09-02 | Glaxosmithkline Llc | 2-Pirimidinil-pirazolopiridinas inhibidoras de la quinasa ErbB |
| UA103319C2 (en) | 2008-05-06 | 2013-10-10 | Глаксосмитклайн Ллк | Thiazole- and oxazole-benzene sulfonamide compounds |
| EP2402335A1 (en) | 2010-06-29 | 2012-01-04 | Basf Se | Pyrazolopyridine compounds |
| EP2402336A1 (en) | 2010-06-29 | 2012-01-04 | Basf Se | Pyrazolopyridine compounds |
| BR112017003745A2 (pt) | 2014-08-29 | 2017-12-05 | Tes Pharma S R L | inibidores de semialdeído descarboxilase de ácido alfa-amino-beta-carboximucônico |
| US9944975B2 (en) | 2015-09-03 | 2018-04-17 | Abbott Molecular Inc. | Hybridization buffers |
| WO2017070089A1 (en) | 2015-10-19 | 2017-04-27 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| RS63762B1 (sr) | 2015-11-19 | 2022-12-30 | Incyte Corp | Heterociklična jedinjenja kao imunomodulatori |
| EP3390361B1 (en) | 2015-12-17 | 2022-03-16 | Incyte Corporation | N-phenyl-pyridine-2-carboxamide derivatives and their use as pd-1/pd-l1 protein/protein interaction modulators |
| TWI767896B (zh) | 2015-12-22 | 2022-06-21 | 美商英塞特公司 | 作為免疫調節劑之雜環化合物 |
| US10457981B2 (en) | 2016-01-08 | 2019-10-29 | Abbott Molecular Inc. | Hybridization buffers |
| AR108396A1 (es) | 2016-05-06 | 2018-08-15 | Incyte Corp | Compuestos heterocíclicos como inmunomoduladores |
| ES2905980T3 (es) | 2016-05-26 | 2022-04-12 | Incyte Corp | Compuestos heterocíclicos como inmunomoduladores |
| CN109890819B (zh) | 2016-06-20 | 2022-11-22 | 因赛特公司 | 作为免疫调节剂的杂环化合物 |
| EP3484866B1 (en) | 2016-07-14 | 2022-09-07 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| WO2018044783A1 (en) | 2016-08-29 | 2018-03-08 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| SMT202200415T1 (it) | 2016-12-22 | 2022-11-18 | Incyte Corp | Derivati di tetraidro imidazo[4,5-c]piridina come induttori di internalizzazione di pd-l1 |
| WO2018119221A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Pyridine derivatives as immunomodulators |
| EP3558963B1 (en) | 2016-12-22 | 2022-03-23 | Incyte Corporation | Bicyclic heteroaromatic compounds as immunomodulators |
| GEAP202215134A (en) | 2016-12-22 | 2022-05-10 | Incyte Corp | Heterocyclic compounds as immunomodulators |
| US20180179201A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| PL4212529T3 (pl) | 2018-03-30 | 2025-07-07 | Incyte Corporation | Związki heterocykliczne jako immunomodulatory |
| JOP20200288A1 (ar) | 2018-05-11 | 2020-11-11 | Incyte Corp | مشتقات تترا هيدرو – إيميدازو[4، 5-c]بيريدين كمعدِّلات مناعية pd-l1 |
| TW202115059A (zh) | 2019-08-09 | 2021-04-16 | 美商英塞特公司 | Ｐｄ—１／ｐｄ—ｌ１抑制劑之鹽 |
| AR120109A1 (es) | 2019-09-30 | 2022-02-02 | Incyte Corp | Compuestos de pirido[3,2-d]pirimidina como inmunomoduladores |
| CR20220237A (es) | 2019-11-11 | 2022-08-05 | Incyte Corp | Sales y formas cristalinas de un inhibidor de pd-1/pd-l1 |
| WO2022099018A1 (en) | 2020-11-06 | 2022-05-12 | Incyte Corporation | Process of preparing a pd-1/pd-l1 inhibitor |
| IL302590A (en) | 2020-11-06 | 2023-07-01 | Incyte Corp | Process for preparing PD-1/PD-L1 inhibitor and salts and crystalline forms thereof |
| TW202233615A (zh) | 2020-11-06 | 2022-09-01 | 美商英塞特公司 | Ｐｄ—１／ｐｄ—ｌ１抑制劑之結晶形式 |
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-
2002
- 2002-03-21 ES ES02723554T patent/ES2266487T3/es not_active Expired - Lifetime
- 2002-03-21 AT AT02723554T patent/ATE332301T1/de not_active IP Right Cessation
- 2002-03-21 US US10/473,491 patent/US7141569B2/en not_active Expired - Fee Related
- 2002-03-21 JP JP2002581427A patent/JP4219171B2/ja not_active Expired - Fee Related
- 2002-03-21 DE DE60212949T patent/DE60212949T2/de not_active Expired - Fee Related
- 2002-03-21 EP EP02723554A patent/EP1377575B1/en not_active Expired - Lifetime
- 2002-03-21 WO PCT/US2002/008793 patent/WO2002083672A1/en not_active Ceased
-
2006
- 2006-06-06 US US11/422,357 patent/US20060235043A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US20060235043A1 (en) | 2006-10-19 |
| US7141569B2 (en) | 2006-11-28 |
| US20040167335A1 (en) | 2004-08-26 |
| JP2004529926A (ja) | 2004-09-30 |
| EP1377575A1 (en) | 2004-01-07 |
| DE60212949T2 (de) | 2007-01-04 |
| DE60212949D1 (de) | 2006-08-17 |
| ES2266487T3 (es) | 2007-03-01 |
| ATE332301T1 (de) | 2006-07-15 |
| WO2002083672A1 (en) | 2002-10-24 |
| EP1377575B1 (en) | 2006-07-05 |
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