CN104725356B - 氮杂环衍生物及其在药物中的应用 - Google Patents
氮杂环衍生物及其在药物中的应用 Download PDFInfo
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- CN104725356B CN104725356B CN201410808777.0A CN201410808777A CN104725356B CN 104725356 B CN104725356 B CN 104725356B CN 201410808777 A CN201410808777 A CN 201410808777A CN 104725356 B CN104725356 B CN 104725356B
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- piperidin
- piperidines
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- 239000003814 drug Substances 0.000 title claims abstract description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 title abstract description 178
- 229910052757 nitrogen Inorganic materials 0.000 title abstract description 95
- 150000001875 compounds Chemical class 0.000 claims abstract description 157
- 206010016654 Fibrosis Diseases 0.000 claims abstract description 55
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 40
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- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 32
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- 208000007342 Diabetic Nephropathies Diseases 0.000 claims abstract description 7
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims abstract description 7
- 206010034665 Peritoneal fibrosis Diseases 0.000 claims abstract description 7
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- 208000019425 cirrhosis of liver Diseases 0.000 claims abstract description 7
- 208000033679 diabetic kidney disease Diseases 0.000 claims abstract description 7
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims abstract description 7
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- -1 C2-4Thiazolinyl Chemical group 0.000 claims description 604
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 105
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- 238000000034 method Methods 0.000 claims description 72
- 229910052731 fluorine Inorganic materials 0.000 claims description 66
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 61
- 229910052794 bromium Inorganic materials 0.000 claims description 55
- 229910052801 chlorine Inorganic materials 0.000 claims description 55
- 229910052740 iodine Inorganic materials 0.000 claims description 48
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 47
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 28
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 28
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 21
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 18
- 125000004104 aryloxy group Chemical group 0.000 claims description 17
- 230000008569 process Effects 0.000 claims description 17
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 17
- 229910021529 ammonia Inorganic materials 0.000 claims description 16
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 14
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 8
- 208000029523 Interstitial Lung disease Diseases 0.000 claims description 6
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims description 6
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- NBVXSUQYWXRMNV-UHFFFAOYSA-N monofluoromethane Natural products FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- 229920002554 vinyl polymer Polymers 0.000 claims description 5
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
- 125000004776 1-fluoroethyl group Chemical group [H]C([H])([H])C([H])(F)* 0.000 claims description 3
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
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- 206010023421 Kidney fibrosis Diseases 0.000 abstract 1
- 206010048654 Muscle fibrosis Diseases 0.000 abstract 1
- 206010028594 Myocardial fibrosis Diseases 0.000 abstract 1
- 206010060932 Postoperative adhesion Diseases 0.000 abstract 1
- 208000004403 Prostatic Hyperplasia Diseases 0.000 abstract 1
- 206010050207 Skin fibrosis Diseases 0.000 abstract 1
- 230000007882 cirrhosis Effects 0.000 abstract 1
- 210000000496 pancreas Anatomy 0.000 abstract 1
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 274
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- 238000010189 synthetic method Methods 0.000 description 225
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 203
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- 238000006243 chemical reaction Methods 0.000 description 166
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- 239000000243 solution Substances 0.000 description 146
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 129
- 150000003053 piperidines Chemical class 0.000 description 91
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 83
- 239000003921 oil Substances 0.000 description 79
- 235000019198 oils Nutrition 0.000 description 79
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 75
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 60
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 59
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 58
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 58
- 125000002619 bicyclic group Chemical group 0.000 description 57
- 235000002639 sodium chloride Nutrition 0.000 description 57
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- 125000000217 alkyl group Chemical group 0.000 description 54
- 125000003545 alkoxy group Chemical group 0.000 description 51
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 51
- 230000004913 activation Effects 0.000 description 50
- 125000003118 aryl group Chemical group 0.000 description 50
- 239000002904 solvent Substances 0.000 description 49
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 48
- 230000006837 decompression Effects 0.000 description 41
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 40
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 38
- 150000002148 esters Chemical class 0.000 description 36
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 35
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 34
- 150000002118 epoxides Chemical class 0.000 description 34
- 125000001072 heteroaryl group Chemical group 0.000 description 34
- 238000000746 purification Methods 0.000 description 34
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 33
- 125000001424 substituent group Chemical group 0.000 description 33
- DPHCXXYPSYMICK-UHFFFAOYSA-N 2-chloro-1-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C(Cl)=C1 DPHCXXYPSYMICK-UHFFFAOYSA-N 0.000 description 32
- 229910000027 potassium carbonate Inorganic materials 0.000 description 30
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 28
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 28
- 235000011181 potassium carbonates Nutrition 0.000 description 28
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 26
- 125000003282 alkyl amino group Chemical group 0.000 description 26
- 229910052799 carbon Inorganic materials 0.000 description 26
- MCVVUJPXSBQTRZ-ONEGZZNKSA-N methyl (e)-but-2-enoate Chemical compound COC(=O)\C=C\C MCVVUJPXSBQTRZ-ONEGZZNKSA-N 0.000 description 26
- 125000004414 alkyl thio group Chemical group 0.000 description 25
- 150000001721 carbon Chemical group 0.000 description 25
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 25
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 23
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 22
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 22
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- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 description 20
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- LUZDYPLAQQGJEA-UHFFFAOYSA-N 2-Methoxynaphthalene Chemical compound C1=CC=CC2=CC(OC)=CC=C21 LUZDYPLAQQGJEA-UHFFFAOYSA-N 0.000 description 19
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 19
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- ROUYFJUVMYHXFJ-UHFFFAOYSA-N tert-butyl 4-oxopiperidine-1-carboxylate Chemical class CC(C)(C)OC(=O)N1CCC(=O)CC1 ROUYFJUVMYHXFJ-UHFFFAOYSA-N 0.000 description 18
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- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 13
- 229910000024 caesium carbonate Inorganic materials 0.000 description 13
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- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 12
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- AIZKHORWEJERNY-UHFFFAOYSA-N 1-(2-chloro-4-nitrophenyl)piperidine Chemical class ClC1=CC([N+](=O)[O-])=CC=C1N1CCCCC1 AIZKHORWEJERNY-UHFFFAOYSA-N 0.000 description 10
- BAGQBTMEEISJLK-UHFFFAOYSA-N 2-fluoronaphthalene Chemical compound C1=CC=CC2=CC(F)=CC=C21 BAGQBTMEEISJLK-UHFFFAOYSA-N 0.000 description 10
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- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 10
- 229910002651 NO3 Inorganic materials 0.000 description 10
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- 238000012805 post-processing Methods 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
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- 125000002768 hydroxyalkyl group Chemical group 0.000 description 8
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- 125000002950 monocyclic group Chemical group 0.000 description 8
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 8
- PDTZMULNKGUIEJ-UHFFFAOYSA-N tert-butyl 4-methylidenepiperidine-1-carboxylate Chemical class CC(C)(C)OC(=O)N1CCC(=C)CC1 PDTZMULNKGUIEJ-UHFFFAOYSA-N 0.000 description 8
- OKDGRDCXVWSXDC-UHFFFAOYSA-N 2-chloropyridine Chemical compound ClC1=CC=CC=N1 OKDGRDCXVWSXDC-UHFFFAOYSA-N 0.000 description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
- 125000003047 N-acetyl group Chemical group 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
- 210000004027 cell Anatomy 0.000 description 7
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- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 7
- MSAXLKSNGBPEES-UHFFFAOYSA-N (2-fluoro-4-nitrophenyl)-phenylmethanone Chemical compound FC1=CC([N+](=O)[O-])=CC=C1C(=O)C1=CC=CC=C1 MSAXLKSNGBPEES-UHFFFAOYSA-N 0.000 description 6
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- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 6
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Classifications
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- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
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- Emergency Medicine (AREA)
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Abstract
Description
Claims (7)
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CN201410808777.0A CN104725356B (zh) | 2013-12-19 | 2014-12-19 | 氮杂环衍生物及其在药物中的应用 |
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CN2013107138408 | 2013-12-19 | ||
CN201310713840 | 2013-12-19 | ||
CN2014101095136 | 2014-03-21 | ||
CN201410109513 | 2014-03-21 | ||
CN201410808777.0A CN104725356B (zh) | 2013-12-19 | 2014-12-19 | 氮杂环衍生物及其在药物中的应用 |
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CN104725356A CN104725356A (zh) | 2015-06-24 |
CN104725356B true CN104725356B (zh) | 2017-02-22 |
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EP (1) | EP3083584B1 (zh) |
JP (1) | JP6454348B2 (zh) |
CN (1) | CN104725356B (zh) |
AU (1) | AU2014366049B2 (zh) |
CA (1) | CA2929394C (zh) |
ES (1) | ES2663806T3 (zh) |
RU (1) | RU2694254C1 (zh) |
WO (1) | WO2015090232A1 (zh) |
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PL3219705T3 (pl) | 2005-12-28 | 2020-08-10 | Vertex Pharmaceuticals Incorporated | Kompozycje farmaceutyczne amorficznych postaci n-[2,4-bis(1,1-dimetyloetylo)-5-hydroksyfenylo]-1,4-dihydro-4-oksochinolino-3-karboksyamidu |
JP6454348B2 (ja) * | 2013-12-19 | 2019-01-16 | サンシャイン・レイク・ファーマ・カンパニー・リミテッドSunshine Lake Pharma Co.,Ltd. | 窒素複素環誘導体およびその医薬品への応用 |
CN107250113B (zh) | 2014-10-07 | 2019-03-29 | 弗特克斯药品有限公司 | 囊性纤维化跨膜传导调节蛋白的调节剂的共晶 |
UA124468C2 (uk) * | 2016-07-28 | 2021-09-22 | Вектус Байосистемз Лімітед | Композиції для лікування легеневого фіброзу |
WO2018112843A1 (en) * | 2016-12-22 | 2018-06-28 | Merck Sharp & Dohme Corp. | Heteroaryl piperidine ether allosteric modulators of the m4 muscarinic acetylcholine receptor |
CN109251175A (zh) * | 2017-07-14 | 2019-01-22 | 广东东阳光药业有限公司 | 嘧啶酮类化合物的制备方法 |
CN109942497A (zh) * | 2019-05-06 | 2019-06-28 | 南京工业大学 | 一种多取代嘧啶酮化合物及其制备方法 |
CN111233673B (zh) * | 2020-02-26 | 2022-08-16 | 苏州元兴生物医药有限公司 | 一种手性芳香族环丙胺及其盐的制备方法及所用中间体 |
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US9902712B2 (en) | 2018-02-27 |
AU2014366049A1 (en) | 2016-05-26 |
EP3083584A4 (en) | 2017-05-10 |
ES2663806T8 (es) | 2018-06-08 |
WO2015090232A1 (en) | 2015-06-25 |
RU2694254C1 (ru) | 2019-07-11 |
CA2929394C (en) | 2021-11-16 |
RU2016129067A (ru) | 2018-01-24 |
US20160355501A1 (en) | 2016-12-08 |
JP2016540800A (ja) | 2016-12-28 |
EP3083584B1 (en) | 2018-02-21 |
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CA2929394A1 (en) | 2015-06-25 |
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