JP2011506474A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2011506474A5 JP2011506474A5 JP2010538183A JP2010538183A JP2011506474A5 JP 2011506474 A5 JP2011506474 A5 JP 2011506474A5 JP 2010538183 A JP2010538183 A JP 2010538183A JP 2010538183 A JP2010538183 A JP 2010538183A JP 2011506474 A5 JP2011506474 A5 JP 2011506474A5
- Authority
- JP
- Japan
- Prior art keywords
- ring
- compound
- optionally substituted
- formula
- hydrogen
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims description 117
- -1 n- propyl Chemical group 0.000 claims description 57
- 239000001257 hydrogen Substances 0.000 claims description 44
- 229910052739 hydrogen Inorganic materials 0.000 claims description 44
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 42
- 125000005842 heteroatom Chemical group 0.000 claims description 40
- 229910052760 oxygen Inorganic materials 0.000 claims description 38
- 229910052717 sulfur Chemical group 0.000 claims description 36
- 125000001931 aliphatic group Chemical group 0.000 claims description 35
- 229910052757 nitrogen Inorganic materials 0.000 claims description 30
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 28
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 28
- 239000001301 oxygen Chemical group 0.000 claims description 28
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
- 239000011593 sulfur Chemical group 0.000 claims description 26
- 125000005843 halogen group Chemical group 0.000 claims description 23
- 125000003118 aryl group Chemical group 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
- 239000000203 mixture Substances 0.000 claims description 19
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 18
- 229920006395 saturated elastomer Polymers 0.000 claims description 18
- 150000002431 hydrogen Chemical class 0.000 claims description 17
- 108010079245 Cystic Fibrosis Transmembrane Conductance Regulator Proteins 0.000 claims description 15
- 102000008371 intracellularly ATP-gated chloride channel activity proteins Human genes 0.000 claims description 15
- 125000002950 monocyclic group Chemical group 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 125000002619 bicyclic group Chemical group 0.000 claims description 14
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 14
- 230000007812 deficiency Effects 0.000 claims description 13
- 102100026383 Vasopressin-neurophysin 2-copeptin Human genes 0.000 claims description 12
- 201000010064 diabetes insipidus Diseases 0.000 claims description 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 230000000694 effects Effects 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- 206010006474 Bronchopulmonary aspergillosis allergic Diseases 0.000 claims description 6
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 6
- 206010033645 Pancreatitis Diseases 0.000 claims description 6
- 208000006778 allergic bronchopulmonary aspergillosis Diseases 0.000 claims description 6
- 239000012472 biological sample Substances 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 239000012634 fragment Substances 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 4
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- LPCQBTAOTIZGAE-UHFFFAOYSA-N 2h-pyrimidine-1-carboxamide Chemical compound NC(=O)N1CN=CC=C1 LPCQBTAOTIZGAE-UHFFFAOYSA-N 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 3
- 102100034452 Alternative prion protein Human genes 0.000 claims description 3
- 208000024827 Alzheimer disease Diseases 0.000 claims description 3
- 102000014461 Ataxins Human genes 0.000 claims description 3
- 108010078286 Ataxins Proteins 0.000 claims description 3
- 206010003694 Atrophy Diseases 0.000 claims description 3
- 206010006458 Bronchitis chronic Diseases 0.000 claims description 3
- 206010008025 Cerebellar ataxia Diseases 0.000 claims description 3
- 208000010693 Charcot-Marie-Tooth Disease Diseases 0.000 claims description 3
- 206010010356 Congenital anomaly Diseases 0.000 claims description 3
- 206010062264 Congenital hyperthyroidism Diseases 0.000 claims description 3
- 206010010774 Constipation Diseases 0.000 claims description 3
- 201000003883 Cystic fibrosis Diseases 0.000 claims description 3
- 208000003556 Dry Eye Syndromes Diseases 0.000 claims description 3
- 206010013883 Dwarfism Diseases 0.000 claims description 3
- 206010014561 Emphysema Diseases 0.000 claims description 3
- 208000024720 Fabry Disease Diseases 0.000 claims description 3
- 201000011240 Frontotemporal dementia Diseases 0.000 claims description 3
- 206010019860 Hereditary angioedema Diseases 0.000 claims description 3
- 208000033981 Hereditary haemochromatosis Diseases 0.000 claims description 3
- 206010060378 Hyperinsulinaemia Diseases 0.000 claims description 3
- 208000000563 Hyperlipoproteinemia Type II Diseases 0.000 claims description 3
- 206010051125 Hypofibrinogenaemia Diseases 0.000 claims description 3
- 208000000038 Hypoparathyroidism Diseases 0.000 claims description 3
- 102100024640 Low-density lipoprotein receptor Human genes 0.000 claims description 3
- 208000019693 Lung disease Diseases 0.000 claims description 3
- 208000007466 Male Infertility Diseases 0.000 claims description 3
- 208000008955 Mucolipidoses Diseases 0.000 claims description 3
- 206010072928 Mucolipidosis type II Diseases 0.000 claims description 3
- 208000002678 Mucopolysaccharidoses Diseases 0.000 claims description 3
- 102100026784 Myelin proteolipid protein Human genes 0.000 claims description 3
- 206010068871 Myotonic dystrophy Diseases 0.000 claims description 3
- 208000018737 Parkinson disease Diseases 0.000 claims description 3
- 208000017493 Pelizaeus-Merzbacher disease Diseases 0.000 claims description 3
- 208000000609 Pick Disease of the Brain Diseases 0.000 claims description 3
- 108091000054 Prion Proteins 0.000 claims description 3
- 201000005660 Protein C Deficiency Diseases 0.000 claims description 3
- 208000021386 Sjogren Syndrome Diseases 0.000 claims description 3
- 208000009415 Spinocerebellar Ataxias Diseases 0.000 claims description 3
- 206010045261 Type IIa hyperlipidaemia Diseases 0.000 claims description 3
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 3
- 208000006673 asthma Diseases 0.000 claims description 3
- 230000037444 atrophy Effects 0.000 claims description 3
- 201000004562 autosomal dominant cerebellar ataxia Diseases 0.000 claims description 3
- 230000002146 bilateral effect Effects 0.000 claims description 3
- 206010006451 bronchitis Diseases 0.000 claims description 3
- 208000007451 chronic bronchitis Diseases 0.000 claims description 3
- 206010012601 diabetes mellitus Diseases 0.000 claims description 3
- 230000004064 dysfunction Effects 0.000 claims description 3
- 208000030172 endocrine system disease Diseases 0.000 claims description 3
- 201000001386 familial hypercholesterolemia Diseases 0.000 claims description 3
- 208000013746 hereditary thrombophilia due to congenital protein C deficiency Diseases 0.000 claims description 3
- 230000003451 hyperinsulinaemic effect Effects 0.000 claims description 3
- 201000008980 hyperinsulinism Diseases 0.000 claims description 3
- 150000002632 lipids Chemical class 0.000 claims description 3
- 208000019423 liver disease Diseases 0.000 claims description 3
- 201000001441 melanoma Diseases 0.000 claims description 3
- 208000020460 mucolipidosis II alpha/beta Diseases 0.000 claims description 3
- 206010028093 mucopolysaccharidosis Diseases 0.000 claims description 3
- 208000000638 myeloperoxidase deficiency Diseases 0.000 claims description 3
- 230000004770 neurodegeneration Effects 0.000 claims description 3
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 3
- 108010040003 polyglutamine Proteins 0.000 claims description 3
- 229920000155 polyglutamine Polymers 0.000 claims description 3
- 201000002212 progressive supranuclear palsy Diseases 0.000 claims description 3
- 230000020978 protein processing Effects 0.000 claims description 3
- 201000009890 sinusitis Diseases 0.000 claims description 3
- 230000000391 smoking effect Effects 0.000 claims description 3
- 208000011580 syndromic disease Diseases 0.000 claims description 3
- 210000001177 vas deferen Anatomy 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 2
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 claims description 2
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 2
- UKDZIHPXUOIUBE-UHFFFAOYSA-N 7-ethyl-4-oxo-n-[3-(trifluoromethyl)-1h-indol-6-yl]-1h-pyrrolo[1,2-a]pyrimidine-3-carboxamide Chemical compound C1=C2C(C(F)(F)F)=CNC2=CC(NC(=O)C2=CNC3=CC(=CN3C2=O)CC)=C1 UKDZIHPXUOIUBE-UHFFFAOYSA-N 0.000 claims description 2
- GNYIWDPHISZCAJ-UHFFFAOYSA-N 7-ethyl-4-oxo-n-[5-(trifluoromethyl)-1h-indol-6-yl]-1h-pyrrolo[1,2-a]pyrimidine-3-carboxamide Chemical compound O=C1N2C=C(CC)C=C2NC=C1C(=O)NC(C(=C1)C(F)(F)F)=CC2=C1C=CN2 GNYIWDPHISZCAJ-UHFFFAOYSA-N 0.000 claims description 2
- QQOPRXFMMROSKY-UHFFFAOYSA-N 7-ethyl-n-[2-fluoro-5-hydroxy-4-(1-methylcyclohexyl)phenyl]-4-oxo-1h-pyrrolo[1,2-a]pyrimidine-3-carboxamide Chemical compound O=C1N2C=C(CC)C=C2NC=C1C(=O)NC(C(=C1)F)=CC(O)=C1C1(C)CCCCC1 QQOPRXFMMROSKY-UHFFFAOYSA-N 0.000 claims description 2
- XGGKIJONYVCYPT-UHFFFAOYSA-N 7-methyl-4-oxo-n-[3-(trifluoromethyl)-1h-indol-6-yl]-1h-pyrrolo[1,2-a]pyrimidine-3-carboxamide Chemical compound C1=C2C(C(F)(F)F)=CNC2=CC(NC(=O)C2=CNC3=CC(=CN3C2=O)C)=C1 XGGKIJONYVCYPT-UHFFFAOYSA-N 0.000 claims description 2
- CXYUDDYJTJSZKY-UHFFFAOYSA-N C1=C(O)C(C(C)(C)C)=CC(C(C)(C)C)=C1NC(=O)C1=CNC2=CC=NN2C1=O Chemical compound C1=C(O)C(C(C)(C)C)=CC(C(C)(C)C)=C1NC(=O)C1=CNC2=CC=NN2C1=O CXYUDDYJTJSZKY-UHFFFAOYSA-N 0.000 claims description 2
- KSMKKIBZTDNPMQ-UHFFFAOYSA-N C=1C=C(NC(=O)C=2C(N3N=CC=C3NC=2)=O)C(C(F)(F)F)=CC=1N1CCCC1 Chemical compound C=1C=C(NC(=O)C=2C(N3N=CC=C3NC=2)=O)C(C(F)(F)F)=CC=1N1CCCC1 KSMKKIBZTDNPMQ-UHFFFAOYSA-N 0.000 claims description 2
- 208000015439 Lysosomal storage disease Diseases 0.000 claims description 2
- XCUAIINAJCDIPM-XVFCMESISA-N N(4)-hydroxycytidine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=NO)C=C1 XCUAIINAJCDIPM-XVFCMESISA-N 0.000 claims description 2
- RKHJVKTUNODYJJ-UHFFFAOYSA-N N1C2=CC=NN2C(=O)C(C(=O)NC2=CC=3NC=CC=3C=C2C(F)(F)F)=C1 Chemical compound N1C2=CC=NN2C(=O)C(C(=O)NC2=CC=3NC=CC=3C=C2C(F)(F)F)=C1 RKHJVKTUNODYJJ-UHFFFAOYSA-N 0.000 claims description 2
- AHVCYAYHVQQESC-UHFFFAOYSA-N N1C2=CC=NN2C(=O)C(C(=O)NC=2C=C3NC=C(C3=CC=2)C(C)(C)C)=C1 Chemical compound N1C2=CC=NN2C(=O)C(C(=O)NC=2C=C3NC=C(C3=CC=2)C(C)(C)C)=C1 AHVCYAYHVQQESC-UHFFFAOYSA-N 0.000 claims description 2
- 208000012902 Nervous system disease Diseases 0.000 claims description 2
- LSVRZDJINJEYOH-UHFFFAOYSA-N O=C1N2N=C(C)C=C2NC=C1C(=O)NC(C(=C1)C(C)(C)C)=CC2=C1C=CN2 Chemical compound O=C1N2N=C(C)C=C2NC=C1C(=O)NC(C(=C1)C(C)(C)C)=CC2=C1C=CN2 LSVRZDJINJEYOH-UHFFFAOYSA-N 0.000 claims description 2
- CJYHLFAIRHUFSG-UHFFFAOYSA-N O=C1N2N=C(C)C=C2NC=C1C(=O)NC1=CC(O)=C(C(C)(C)C)C=C1C(C)(C)C Chemical compound O=C1N2N=C(C)C=C2NC=C1C(=O)NC1=CC(O)=C(C(C)(C)C)C=C1C(C)(C)C CJYHLFAIRHUFSG-UHFFFAOYSA-N 0.000 claims description 2
- 208000024777 Prion disease Diseases 0.000 claims description 2
- 208000004622 abetalipoproteinemia Diseases 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 2
- 229960005475 antiinfective agent Drugs 0.000 claims description 2
- 239000004599 antimicrobial Substances 0.000 claims description 2
- 229940124630 bronchodilator Drugs 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
- 239000003172 expectorant agent Substances 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 238000000338 in vitro Methods 0.000 claims description 2
- 238000001727 in vivo Methods 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 229940066491 mucolytics Drugs 0.000 claims description 2
- KTEBEMMMLNIPHB-UHFFFAOYSA-N n-(2,4-ditert-butyl-5-hydroxyphenyl)-7-ethyl-4-oxo-1h-pyrrolo[1,2-a]pyrimidine-3-carboxamide Chemical compound O=C1N2C=C(CC)C=C2NC=C1C(=O)NC1=CC(O)=C(C(C)(C)C)C=C1C(C)(C)C KTEBEMMMLNIPHB-UHFFFAOYSA-N 0.000 claims description 2
- VXBPRKYNBFJTAB-UHFFFAOYSA-N n-(3-tert-butyl-1h-indol-6-yl)-7-ethyl-4-oxo-1h-pyrrolo[1,2-a]pyrimidine-3-carboxamide Chemical compound C1=C2C(C(C)(C)C)=CNC2=CC(NC(=O)C2=CNC3=CC(=CN3C2=O)CC)=C1 VXBPRKYNBFJTAB-UHFFFAOYSA-N 0.000 claims description 2
- QSGVSPNYFDSCOM-UHFFFAOYSA-N n-[2-fluoro-5-hydroxy-4-(1-methylcyclohexyl)phenyl]-7-methyl-4-oxo-1h-pyrrolo[1,2-a]pyrimidine-3-carboxamide Chemical compound O=C1N2C=C(C)C=C2NC=C1C(=O)NC(C(=C1)F)=CC(O)=C1C1(C)CCCCC1 QSGVSPNYFDSCOM-UHFFFAOYSA-N 0.000 claims description 2
- YFNMNJHCEMBBAU-UHFFFAOYSA-N n-[4-(3,3-dimethylpyrrolidin-1-yl)-2-(trifluoromethyl)phenyl]-7-methyl-4-oxo-1h-pyrrolo[1,2-a]pyrimidine-3-carboxamide Chemical compound O=C1N2C=C(C)C=C2NC=C1C(=O)NC(C(=C1)C(F)(F)F)=CC=C1N1CCC(C)(C)C1 YFNMNJHCEMBBAU-UHFFFAOYSA-N 0.000 claims description 2
- ICPUHOLYWHUUGE-UHFFFAOYSA-N n-[4-cyclopentyl-5-hydroxy-2-(trifluoromethyl)phenyl]-7-methyl-4-oxo-1h-pyrrolo[1,2-a]pyrimidine-3-carboxamide Chemical compound O=C1N2C=C(C)C=C2NC=C1C(=O)NC(C(=C1)C(F)(F)F)=CC(O)=C1C1CCCC1 ICPUHOLYWHUUGE-UHFFFAOYSA-N 0.000 claims description 2
- 230000001537 neural effect Effects 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 235000015097 nutrients Nutrition 0.000 claims description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 230000001898 pallidal effect Effects 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- HKSQZEGSMBFHGC-UHFFFAOYSA-N pyrimidine-4-carboxamide Chemical compound NC(=O)C1=CC=NC=N1 HKSQZEGSMBFHGC-UHFFFAOYSA-N 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 125000006413 ring segment Chemical group 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000001425 triazolyl group Chemical group 0.000 claims description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- 208000013558 Developmental Bone disease Diseases 0.000 claims 1
- 206010028289 Muscle atrophy Diseases 0.000 claims 1
- 206010072610 Skeletal dysplasia Diseases 0.000 claims 1
- 230000003115 biocidal effect Effects 0.000 claims 1
- 208000019715 inherited Creutzfeldt-Jakob disease Diseases 0.000 claims 1
- 230000020763 muscle atrophy Effects 0.000 claims 1
- 201000000585 muscular atrophy Diseases 0.000 claims 1
- 210000000463 red nucleus Anatomy 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 125000001118 alkylidene group Chemical group 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 0 C*C=C(N(*)C(*)=C1C(N(*)c2c(C3CCCCCCC3)cccc2)=O)N(*)C1=O Chemical compound C*C=C(N(*)C(*)=C1C(N(*)c2c(C3CCCCCCC3)cccc2)=O)N(*)C1=O 0.000 description 2
- 208000020406 Creutzfeldt Jacob disease Diseases 0.000 description 2
- 208000003407 Creutzfeldt-Jakob Syndrome Diseases 0.000 description 2
- 208000010859 Creutzfeldt-Jakob disease Diseases 0.000 description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 125000006217 methyl sulfide group Chemical group [H]C([H])([H])S* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 208000002320 spinal muscular atrophy Diseases 0.000 description 2
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 description 1
- DLNKGPWYATYSSQ-UHFFFAOYSA-N CN(C)[IH]c1cccc2c1cc[nH]2 Chemical compound CN(C)[IH]c1cccc2c1cc[nH]2 DLNKGPWYATYSSQ-UHFFFAOYSA-N 0.000 description 1
- HMMPHXCOTBASBC-UHFFFAOYSA-N Cc1ccc(cn[nH]2)c2c1 Chemical compound Cc1ccc(cn[nH]2)c2c1 HMMPHXCOTBASBC-UHFFFAOYSA-N 0.000 description 1
- 208000017701 Endocrine disease Diseases 0.000 description 1
- 206010031243 Osteogenesis imperfecta Diseases 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 125000005362 aryl sulfone group Chemical group 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 239000000168 bronchodilator agent Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 210000003591 cerebellar nuclei Anatomy 0.000 description 1
- 230000009089 cytolysis Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 230000002132 lysosomal effect Effects 0.000 description 1
- 201000001119 neuropathy Diseases 0.000 description 1
- 230000007823 neuropathy Effects 0.000 description 1
- 230000011164 ossification Effects 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1333607P | 2007-12-13 | 2007-12-13 | |
| US61/013,336 | 2007-12-13 | ||
| PCT/US2008/086562 WO2009076593A1 (en) | 2007-12-13 | 2008-12-12 | Modulators of cystic fibrosis transmembrane conductance regulator |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011506474A JP2011506474A (ja) | 2011-03-03 |
| JP2011506474A5 true JP2011506474A5 (enExample) | 2013-02-07 |
| JP5637859B2 JP5637859B2 (ja) | 2014-12-10 |
Family
ID=40404952
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010538183A Active JP5637859B2 (ja) | 2007-12-13 | 2008-12-12 | 嚢胞性線維症膜コンダクタンスレギュレーターのモジュレーター |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US8552006B2 (enExample) |
| EP (1) | EP2231671B1 (enExample) |
| JP (1) | JP5637859B2 (enExample) |
| CN (1) | CN101925603B (enExample) |
| AU (1) | AU2008335031B2 (enExample) |
| CA (1) | CA2709301C (enExample) |
| ES (1) | ES2422741T3 (enExample) |
| NZ (1) | NZ586271A (enExample) |
| WO (1) | WO2009076593A1 (enExample) |
Families Citing this family (94)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7973169B2 (en) | 2003-09-06 | 2011-07-05 | Vertex Pharmaceuticals Incorporated | Modulators of ATP-Binding Cassette transporters |
| ATE437640T1 (de) * | 2003-11-14 | 2009-08-15 | Vertex Pharma | Thiazole udn oxazole als modulatoren von atp- bindungs-kassetten-transportern |
| US7977322B2 (en) | 2004-08-20 | 2011-07-12 | Vertex Pharmaceuticals Incorporated | Modulators of ATP-binding cassette transporters |
| PL2502911T3 (pl) * | 2004-06-24 | 2017-09-29 | Vertex Pharma | Modulatory transporterów kasety wiążącej ATP |
| CA2618057A1 (en) | 2005-08-11 | 2007-02-22 | Vertex Pharmaceuticals Incorporated | Modulators of cystic fibrosis transmembrane conductance regulator |
| DK1945632T3 (da) | 2005-11-08 | 2013-12-16 | Vertex Pharma | Heterocycliske modulatorer af ATP-bindende kassettetransportører |
| CN101395147B (zh) | 2005-12-28 | 2013-05-29 | 弗特克斯药品有限公司 | 作为atp-结合盒转运蛋白调节剂用于治疗囊性纤维化的1-(苯并[d][1,3]间二氧杂环戊烯-5-基)-n-(苯基)环丙烷-甲酰胺衍生物及相关化合物 |
| WO2007079139A2 (en) | 2005-12-28 | 2007-07-12 | Vertex Pharmaceuticals, Inc. | Solid forms of n-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide |
| US7671221B2 (en) * | 2005-12-28 | 2010-03-02 | Vertex Pharmaceuticals Incorporated | Modulators of ATP-Binding Cassette transporters |
| USRE50453E1 (en) | 2006-04-07 | 2025-06-10 | Vertex Pharmaceuticals Incorporated | Indole derivatives as CFTR modulators |
| US10022352B2 (en) | 2006-04-07 | 2018-07-17 | Vertex Pharmaceuticals Incorporated | Modulators of ATP-binding cassette transporters |
| US7645789B2 (en) | 2006-04-07 | 2010-01-12 | Vertex Pharmaceuticals Incorporated | Indole derivatives as CFTR modulators |
| DK2007756T3 (en) | 2006-04-07 | 2015-10-05 | Vertex Pharma | MODULATORS OF ATP BINDING CASSETTE TRANSPORT |
| US8563573B2 (en) | 2007-11-02 | 2013-10-22 | Vertex Pharmaceuticals Incorporated | Azaindole derivatives as CFTR modulators |
| EP2789606B1 (en) | 2007-05-09 | 2017-11-15 | Vertex Pharmaceuticals Incorporated | Modulators of CFTR |
| JP5389030B2 (ja) | 2007-08-24 | 2014-01-15 | 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 | （特に）嚢胞性線維症の処置に有用なイソチアゾロピリジノン |
| PL2578571T3 (pl) | 2007-11-16 | 2016-03-31 | Vertex Pharma | Modulatory izochinolinowe transporterów zawierających kasetę wiążącą ATP |
| US20110092554A1 (en) * | 2007-11-19 | 2011-04-21 | Richard Chesworth | 1,3,5 tri-subtituted benzenes for treatment of alzheimer's disease and other disorders |
| KR20160040745A (ko) | 2007-12-07 | 2016-04-14 | 버텍스 파마슈티칼스 인코포레이티드 | 3-(6-(1-(2,2-디플루오로벤조[ｄ][1,3]디옥솔-5-일)사이클로프로판카복스아미도)-3-메틸피리딘-2-일)벤조산의 고체 형태 |
| US20100036130A1 (en) | 2007-12-07 | 2010-02-11 | Vertex Pharmaceuticals Incorporated | Processes for producing cycloalkylcarboxamido-pyridine benzoic acids |
| ES2604555T3 (es) * | 2007-12-07 | 2017-03-07 | Vertex Pharmaceuticals Incorporated | Procedimiento para producir ácidos cicloalquilcarboxiamido-piridinabenzoicos |
| US20090176839A1 (en) * | 2007-12-07 | 2009-07-09 | Ali Keshavarz-Shokri | Formulations of 3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl) cyclopropanecarboxamido)-3-methylpyridin-2-yl)benzoic acid |
| US8217064B2 (en) | 2007-12-20 | 2012-07-10 | Envivo Pharmaceuticals, Inc. | Tetrasubstituted benzenes |
| NZ720282A (en) | 2008-02-28 | 2017-12-22 | Vertex Pharma | Heteroaryl derivatives as cftr modulators |
| CN103951614A (zh) | 2008-03-31 | 2014-07-30 | 沃泰克斯药物股份有限公司 | 作为cftr调节剂的吡啶基衍生物 |
| US20100074949A1 (en) | 2008-08-13 | 2010-03-25 | William Rowe | Pharmaceutical composition and administration thereof |
| US12458635B2 (en) | 2008-08-13 | 2025-11-04 | Vertex Pharmaceuticals Incorporated | Pharmaceutical composition and administrations thereof |
| AR073709A1 (es) | 2008-09-29 | 2010-11-24 | Vertex Pharma | Unidades de dosis de acido 3-(6-(1-(2,2-difluorobenzeno (d) (1,3) dioxol-5-il) ciclopropancarboxamido)-3-metilpiridin-2-il) benzoico |
| DK2349263T3 (da) * | 2008-10-23 | 2014-07-21 | Vertex Pharma | Modulatorer af transmembranledningsevneregulatoren for cystisk fibrose |
| WO2010068863A2 (en) | 2008-12-12 | 2010-06-17 | Cystic Fibrosis Foundation Therapeutics, Inc. | Pyrimidine compounds and methods of making and using same |
| CA3071058C (en) | 2009-03-20 | 2023-01-24 | Vertex Pharmaceuticals Incorporated | Process for making modulators of cystic fibrosis transmembrane conductance regulator |
| WO2011008931A2 (en) * | 2009-07-15 | 2011-01-20 | Cystic Fibrosis Foundation Therapeutics, Inc. | Arylpyrimidine compounds and combination therapy comprising same for treating cystic fibrosis & related disorders |
| IN2012DN00719A (enExample) * | 2009-08-10 | 2015-06-19 | Univ California | |
| US8247436B2 (en) * | 2010-03-19 | 2012-08-21 | Novartis Ag | Pyridine and pyrazine derivative for the treatment of CF |
| US8802868B2 (en) | 2010-03-25 | 2014-08-12 | Vertex Pharmaceuticals Incorporated | Solid forms of (R)-1(2,2-difluorobenzo[D][1,3]dioxo1-5-yl)-N-(1-(2,3-dihydroxypropyl-6-fluoro-2-(1-hydroxy-2-methylpropan2-yl)-1H-Indol-5-yl)-Cyclopropanecarboxamide |
| CA2795514A1 (en) * | 2010-04-05 | 2011-10-13 | Cadila Pharmaceuticals Limited | Novel hypoglycemic compounds |
| CN102933206A (zh) | 2010-04-07 | 2013-02-13 | 弗特克斯药品有限公司 | 3-(6-(1-(2，2-二氟苯并[d][1，3]二氧杂环戊烯-5-基)环丙烷甲酰胺基)-3-甲基吡啶-2-基)苯甲酸的固体形式 |
| NZ602838A (en) | 2010-04-07 | 2015-06-26 | Vertex Pharma | Pharmaceutical compositions of 3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl) cyclopropanecarboxamido)-3-methylpyridin-2-yl)benzoic acid and administration thereof |
| KR20130056244A (ko) | 2010-04-22 | 2013-05-29 | 버텍스 파마슈티칼스 인코포레이티드 | 시클로알킬카르복스아미도-인돌 화합물의 제조 방법 |
| US8563593B2 (en) | 2010-06-08 | 2013-10-22 | Vertex Pharmaceuticals Incorporated | Formulations of (R)-1-(2,2-difluorobenzo[D] [1,3] dioxol-5-yl)-N-(1-(2,3-dihydroxypropyl)-6-fluoro-2-(1-hydroxy-2-methylpropan-2-yl)-1H-indol-5-yl)cyclopropanecarboxamide |
| US8334292B1 (en) | 2010-06-14 | 2012-12-18 | Cystic Fibrosis Foundation Therapeutics, Inc. | Pyrimidine compounds and methods of making and using same |
| USRE48842E1 (en) | 2011-05-27 | 2021-12-07 | The Regents Of The University Of California | Pyrimido-pyrrolo-oxazine-dione compound inhibitors of the cystic fibrosis transmembrane conductance regulator protein and uses therefor |
| US9056867B2 (en) | 2011-09-16 | 2015-06-16 | Novartis Ag | N-substituted heterocyclyl carboxamides |
| KR101985044B1 (ko) | 2011-11-08 | 2019-05-31 | 버텍스 파마슈티칼스 인코포레이티드 | Atp-결합 카세트 수송체의 조절제 |
| PT2806859T (pt) | 2012-01-25 | 2019-09-04 | Vertex Pharma | Formulações de ácido 3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-il)ciclopropanocarboxamido)-3-metilpiridin-2-il)benzoico |
| MX389751B (es) | 2012-02-27 | 2025-03-20 | Vertex Pharma | Composición farmacéutica y administraciones de la misma. |
| US8674108B2 (en) | 2012-04-20 | 2014-03-18 | Vertex Pharmaceuticals Incorporated | Solid forms of N-[2,4-bis(1,1-dimethylethy)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide |
| AU2013290444B2 (en) | 2012-07-16 | 2018-04-26 | Vertex Pharmaceuticals Incorporated | Pharmaceutical compositions of (R)-1-(2,2-diflurorbenzo[d][1,3]dioxol-5-yl)-N-(1-(2,3-dihydroxypropyl)-6-fluoro-2-(1-hydroxy-2-methylpropan-2-yl)-1H-indol-5-yl) cyclopropanecarboxamide and administration thereof |
| CA2904760A1 (en) | 2013-03-13 | 2014-09-18 | Genentech, Inc. | Pyrazolo compounds and uses thereof |
| WO2015073231A1 (en) | 2013-11-12 | 2015-05-21 | Vertex Pharmaceuticals Incorporated | Process of preparing pharmaceutical compositions for the treatment of cftr mediated diseases |
| KR102447581B1 (ko) | 2014-04-15 | 2022-09-28 | 버텍스 파마슈티칼스 인코포레이티드 | 낭포성 섬유증 막전도 조절자 매개 질환 치료용 약제학적 조성물 |
| RU2749213C2 (ru) | 2014-10-07 | 2021-06-07 | Вертекс Фармасьютикалз Инкорпорейтед | Сокристаллы модуляторов регулятора трансмембранной проводимости при кистозном фиброзе |
| AU2014409485A1 (en) * | 2014-10-21 | 2017-05-11 | Accenture Global Services Limited | System, method, and apparatus for capacity determination for micro grid, and tangible computer readable medium |
| JP6615213B2 (ja) | 2014-10-31 | 2019-12-04 | アッヴィ・エス・ア・エール・エル | 置換テトラヒドロピランおよび使用方法 |
| SG11201703963QA (en) | 2014-11-18 | 2017-06-29 | Vertex Pharma | Process of conducting high throughput testing high performance liquid chromatography |
| RU2017146661A (ru) | 2015-06-02 | 2019-07-15 | Эббви С.А.Р.Л. | Замещенные пиридины и способ их применения |
| US9840513B2 (en) | 2015-07-16 | 2017-12-12 | Abbvie S.Á.R.L. | Substituted tricyclics and method of use |
| KR20250136942A (ko) | 2015-10-06 | 2025-09-16 | 프로테오스타시스 테라퓨틱스, 인크. | Cftr 조절용 화합물, 조성물, 및 방법 |
| SI3359541T1 (sl) | 2015-10-09 | 2021-01-29 | Abbvie Overseas S.A R.L. | N-sulfonirani pirazolo(3,4 b)piridin-6-karboksamidi in postopki uporabe |
| CA3000802A1 (en) | 2015-10-09 | 2017-04-13 | Abbvie S.A.R.L. | Compounds for treatment of cystic fibrosis |
| CN108431002A (zh) | 2015-10-09 | 2018-08-21 | 艾伯维公司 | 取代的吡唑并[3，4-b]吡啶-6-甲酸及其用途 |
| EP3448842A1 (en) | 2016-04-26 | 2019-03-06 | AbbVie S.À.R.L. | Modulators of cystic fibrosis transmembrane conductance regulator protein |
| US10138227B2 (en) | 2016-06-03 | 2018-11-27 | Abbvie S.Á.R.L. | Heteroaryl substituted pyridines and methods of use |
| US10399940B2 (en) | 2016-10-07 | 2019-09-03 | Abbvie S.Á.R.L. | Substituted pyrrolidines and methods of use |
| US9981910B2 (en) | 2016-10-07 | 2018-05-29 | Abbvie S.Á.R.L. | Substituted pyrrolidines and methods of use |
| US20200123137A1 (en) | 2016-12-20 | 2020-04-23 | AbbVie S.à.r.l. | Deuterated cftr modulators and methods of use |
| AR110401A1 (es) * | 2016-12-21 | 2019-03-27 | Chiesi Farm Spa | Derivados dihidropirimidina bicíclica-carboxamida como inhibidores de rho-quinasa |
| TW201831471A (zh) | 2017-02-24 | 2018-09-01 | 盧森堡商艾伯維公司 | 囊腫纖化症跨膜傳導調節蛋白的調節劑及其使用方法 |
| US10988454B2 (en) | 2017-09-14 | 2021-04-27 | Abbvie Overseas S.À.R.L. | Modulators of the cystic fibrosis transmembrane conductance regulator protein and methods of use |
| TW201920185A (zh) * | 2017-09-15 | 2019-06-01 | 美商艾杜諾生物科技公司 | 吡唑并嘧啶酮化合物及其用途 |
| WO2019193062A1 (en) | 2018-04-03 | 2019-10-10 | Abbvie S.Á.R.L | Substituted pyrrolidines and their use |
| US11345691B2 (en) | 2019-06-03 | 2022-05-31 | AbbVie Global Enterprises Ltd. | Prodrug modulators of the cystic fibrosis transmembrane conductance regulator protein and methods of use |
| WO2021011327A1 (en) | 2019-07-12 | 2021-01-21 | Orphomed, Inc. | Compound for treating cystic fibrosis |
| WO2021097054A1 (en) | 2019-11-12 | 2021-05-20 | Genzyme Corporation | 6-membered heteroarylaminosulfonamides for treating diseases and conditions mediated by deficient cftr activity |
| WO2021113806A1 (en) | 2019-12-05 | 2021-06-10 | Genzyme Corporation | Arylamides and methods of use thereof |
| WO2021113809A1 (en) | 2019-12-05 | 2021-06-10 | Genzyme Corporation | Arylamides and methods of use thereof |
| PH12022551379A1 (en) | 2019-12-06 | 2023-05-03 | Vertex Pharma | Substituted tetrahydrofurans as modulators of sodium channels |
| TWI775313B (zh) | 2020-02-18 | 2022-08-21 | 美商基利科學股份有限公司 | 抗病毒化合物 |
| EP4106876B1 (en) | 2020-02-18 | 2025-09-17 | Gilead Sciences, Inc. | Antiviral compounds |
| TWI794742B (zh) | 2020-02-18 | 2023-03-01 | 美商基利科學股份有限公司 | 抗病毒化合物 |
| CR20230120A (es) | 2020-08-07 | 2023-09-01 | Vertex Pharma | Moduladores del regulador de la conductancia transmembrana de la fibrosis quística |
| WO2022084741A1 (en) * | 2020-10-23 | 2022-04-28 | Ildong Pharmaceutical Co., Ltd. | Cftr modulator compounds, compositions, and uses thereof |
| US12324802B2 (en) | 2020-11-18 | 2025-06-10 | Vertex Pharmaceuticals Incorporated | Modulators of cystic fibrosis transmembrane conductance regulator |
| WO2022150173A1 (en) | 2021-01-06 | 2022-07-14 | AbbVie Global Enterprises Ltd. | Modulators of the cystic fibrosis transmembrane conductance regulator protein and methods of use |
| WO2022150174A1 (en) | 2021-01-06 | 2022-07-14 | AbbVie Global Enterprises Ltd. | Modulators of the cystic fibrosis transmembrane conductance regulator protein and methods of use |
| EP4323362B1 (en) | 2021-04-16 | 2025-05-07 | Gilead Sciences, Inc. | Methods of preparing carbanucleosides using amides |
| DK4347031T3 (da) | 2021-06-04 | 2025-12-01 | Vertex Pharma | N-(hydroxyalkyl-(hetero)aryl)-tetrahydrofuran-carboxamider som modulatorer af natriumkanaler |
| JP7719954B2 (ja) | 2021-08-18 | 2025-08-06 | ギリアード サイエンシーズ， インコーポレイテッド | リン脂質化合物並びにその製造方法及び使用方法 |
| MX2024002519A (es) | 2021-09-03 | 2024-05-27 | Genzyme Corp | Compuestos de indol y metodos de uso. |
| WO2023034946A1 (en) | 2021-09-03 | 2023-03-09 | Genzyme Corporation | Indole compounds and uses thereof in the treatement of cystic fibrosis |
| WO2024054845A1 (en) | 2022-09-07 | 2024-03-14 | Sionna Therapeutics | Macrocycic compounds, compositions, and methods of using thereof |
| KR20250091331A (ko) | 2022-09-07 | 2025-06-20 | 시오나 테라퓨틱스 인크. | 거대환식 화합물, 조성물, 및 이의 사용 방법 |
| WO2024054851A1 (en) | 2022-09-07 | 2024-03-14 | Sionna Therapeutics | Macrocyclic compounds, compositions and methods of using thereof |
| WO2025132358A1 (en) | 2023-12-21 | 2025-06-26 | Galapagos Nv | Novel compounds and pharmaceutical compositions thereof for the treatment of infectious diseases |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992006096A1 (fr) * | 1990-10-09 | 1992-04-16 | Otsuka Pharmaceutical Co., Ltd. | Derive de pyrimidine, production de ce derive et inhibiteur d'androgenes |
| ATE305008T1 (de) * | 1999-10-15 | 2005-10-15 | Neurocrine Biosciences Inc | Gonadotropin freisetzenden hormon rezeptor antagonisten und ihre verwandten verwendungen |
| PL2502911T3 (pl) * | 2004-06-24 | 2017-09-29 | Vertex Pharma | Modulatory transporterów kasety wiążącej ATP |
| CA2688004C (en) * | 2007-05-25 | 2016-07-05 | Vertex Pharmaceuticals Incorporated | Thienopyridone compounds for use as modulators of cystic fibrosis transmembrane conductance regulator |
| JP5389030B2 (ja) * | 2007-08-24 | 2014-01-15 | 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 | （特に）嚢胞性線維症の処置に有用なイソチアゾロピリジノン |
-
2008
- 2008-12-12 JP JP2010538183A patent/JP5637859B2/ja active Active
- 2008-12-12 ES ES08859265T patent/ES2422741T3/es active Active
- 2008-12-12 AU AU2008335031A patent/AU2008335031B2/en not_active Ceased
- 2008-12-12 CA CA2709301A patent/CA2709301C/en active Active
- 2008-12-12 NZ NZ586271A patent/NZ586271A/xx not_active IP Right Cessation
- 2008-12-12 EP EP08859265.4A patent/EP2231671B1/en active Active
- 2008-12-12 CN CN2008801255937A patent/CN101925603B/zh not_active Expired - Fee Related
- 2008-12-12 WO PCT/US2008/086562 patent/WO2009076593A1/en not_active Ceased
-
2010
- 2010-06-11 US US12/813,876 patent/US8552006B2/en active Active
-
2013
- 2013-09-05 US US14/018,983 patent/US9051324B2/en active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2011506474A5 (enExample) | ||
| JP2010528050A5 (enExample) | ||
| JP5637859B2 (ja) | 嚢胞性線維症膜コンダクタンスレギュレーターのモジュレーター | |
| JP2008504291A5 (enExample) | ||
| JP2012514038A5 (enExample) | ||
| JP2010539185A5 (enExample) | ||
| CA2696298C (en) | Modulators of cystic fibrosis transmembrane conductance regulator | |
| US8399479B2 (en) | Modulators of cystic fibrosis transmembrane conductance regulator | |
| JP2009521468A5 (enExample) | ||
| JP2007519740A5 (enExample) | ||
| JP2013245219A5 (enExample) | ||
| JP2011513321A5 (enExample) | ||
| JP2010526831A5 (enExample) | ||
| JP2011505338A5 (enExample) | ||
| JP2011516420A5 (enExample) | ||
| JP2012521362A5 (enExample) | ||
| JP2009522277A5 (enExample) | ||
| RU2010114732A (ru) | Твердые формы n-[2,4-бис(1,1-диметилэтил)-5-гидроксифенил]-1,4-дигидро-4-оксохинолин-3-карбоксамида | |
| JP2013508414A5 (enExample) | ||
| RU2009142030A (ru) | Модуляторы транспортеров атф-связывающей кассеты | |
| RU2007102578A (ru) | Модуляторы транспортеров атф-связывающей кассеты | |
| HK1146934B (en) | Modulators of cystic fibrosis transmembrane conductance regulator |