JP2011506474A5 - - Google Patents
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- 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
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- compound
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- hydrogen
- Prior art date
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- 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
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- 206010010356 Congenital anomaly Diseases 0.000 claims description 3
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- 102100024640 Low-density lipoprotein receptor Human genes 0.000 claims description 3
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- 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
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- 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
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- 208000020460 mucolipidosis II alpha/beta Diseases 0.000 claims description 3
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- 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
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- 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
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- 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
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- 208000019715 inherited Creutzfeldt-Jakob disease Diseases 0.000 claims 1
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- 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
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- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 2
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- 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
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- 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 (OSRAM) | 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 (OSRAM) |
| EP (1) | EP2231671B1 (OSRAM) |
| JP (1) | JP5637859B2 (OSRAM) |
| CN (1) | CN101925603B (OSRAM) |
| AU (1) | AU2008335031B2 (OSRAM) |
| CA (1) | CA2709301C (OSRAM) |
| ES (1) | ES2422741T3 (OSRAM) |
| NZ (1) | NZ586271A (OSRAM) |
| WO (1) | WO2009076593A1 (OSRAM) |
Families Citing this family (93)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA200602755B (en) | 2003-09-06 | 2007-06-27 | Vertex Pharma | Modulators of ATP-binding cassette transporters |
| JP4869072B2 (ja) * | 2003-11-14 | 2012-02-01 | 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 | Ａｔｐ結合カセットトランスポーターのモジュレーターとして有用なチアゾールおよびオキサゾール |
| US7977322B2 (en) | 2004-08-20 | 2011-07-12 | Vertex Pharmaceuticals Incorporated | Modulators of ATP-binding cassette transporters |
| NZ587549A (en) * | 2004-06-24 | 2012-10-26 | Vertex Pharma | 6-Amino-indole derivatives and processes for their preparation |
| EP1912983B1 (en) | 2005-08-11 | 2011-06-08 | Vertex Pharmaceuticals, Inc. | Modulators of cystic fibrosis transmembrane conductance regulator |
| KR101331768B1 (ko) * | 2005-11-08 | 2013-11-22 | 버텍스 파마슈티칼스 인코포레이티드 | Ａｔｐ 결합 카세트 수송체의 헤테로사이클릭 조정제 |
| CA2635581C (en) | 2005-12-28 | 2017-02-28 | Vertex Pharmaceuticals Incorporated | Solid forms of n-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide |
| CA2856037C (en) * | 2005-12-28 | 2017-03-07 | Vertex Pharmaceuticals Incorporated | Modulators of atp-binding cassette transporters |
| US7671221B2 (en) * | 2005-12-28 | 2010-03-02 | Vertex Pharmaceuticals Incorporated | Modulators of ATP-Binding Cassette transporters |
| PL2674428T3 (pl) | 2006-04-07 | 2017-01-31 | Vertex Pharmaceuticals Incorporated | Modulatory transporterów z kasetą wiążącą ATP |
| 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 |
| US8563573B2 (en) | 2007-11-02 | 2013-10-22 | Vertex Pharmaceuticals Incorporated | Azaindole derivatives as CFTR modulators |
| CA2686838C (en) | 2007-05-09 | 2017-03-14 | Vertex Pharmaceuticals Incorporated | Modulators of cftr |
| AU2008302598B2 (en) | 2007-08-24 | 2014-07-17 | Vertex Pharmaceuticals Incorporated | Isothiazolopyridinones useful for the treatment of (inter alia) Cystic Fibrosis |
| SI2578571T1 (sl) | 2007-11-16 | 2016-01-29 | Vertex Pharmaceuticals Incorporated | Izokinolinski modulatorji prenašalcev z atp-vezavno kaseto |
| WO2009067493A2 (en) * | 2007-11-19 | 2009-05-28 | Envivo Pharmaceuticals, Inc. | 1,3,5 tri-subtituted benzenes for treatment of alzheimer's disease and other disorders |
| DK2639223T3 (en) | 2007-12-07 | 2017-06-19 | Vertex Pharma | Process for Preparation of Cycloalkylcarboxiamido-pyridine Benzoic Acids |
| HRP20170241T2 (hr) | 2007-12-07 | 2023-03-17 | Vertex Pharmaceuticals Incorporated | Čvrsti oblici 3-(6-(1-(2,2-difluorobenzo[d][1,3]dioksol-5-il)ciklopropankarboksamido)-3-metilpiridin-2-il)benzojeve kiseline |
| AU2008335439A1 (en) * | 2007-12-07 | 2009-06-18 | Vertex Pharmaceuticals Incorporated | Formulations of 3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl) cyclopropanecarboxamido)-3-methylpyridin-2-yl)benzoic acid |
| US20100036130A1 (en) | 2007-12-07 | 2010-02-11 | Vertex Pharmaceuticals Incorporated | Processes for producing cycloalkylcarboxamido-pyridine benzoic acids |
| US8217064B2 (en) | 2007-12-20 | 2012-07-10 | Envivo Pharmaceuticals, Inc. | Tetrasubstituted benzenes |
| NZ736561A (en) | 2008-02-28 | 2018-02-23 | Vertex Pharma | Heteroaryl derivatives as cftr modulators |
| DK2615085T3 (en) | 2008-03-31 | 2015-10-05 | Vertex Pharma | Pyridyl derivatives as CFTR modulators |
| US12458635B2 (en) | 2008-08-13 | 2025-11-04 | Vertex Pharmaceuticals Incorporated | Pharmaceutical composition and administrations thereof |
| US20100074949A1 (en) | 2008-08-13 | 2010-03-25 | William Rowe | Pharmaceutical composition and administration thereof |
| US8716338B2 (en) * | 2008-09-29 | 2014-05-06 | Vertex Pharmaceuticals Incorporated | Dosage units of 3-(6-(1-(2,2-difluorobenzo[D] [1,3] dioxol-5-yl) cyclopropanecarboxamido)-3-methylpyridin-2-yl)benzoic acid |
| UA104601C2 (uk) * | 2008-10-23 | 2014-02-25 | Вертекс Фармасьютікалз, Інкорпорейтед | Модулятори регулятора трансмембранної провідності при муковісцидозі |
| WO2010068863A2 (en) | 2008-12-12 | 2010-06-17 | Cystic Fibrosis Foundation Therapeutics, Inc. | Pyrimidine compounds and methods of making and using same |
| PL2408750T3 (pl) | 2009-03-20 | 2016-02-29 | Vertex Pharma | Sposób otrzymywania modulatorów błonowego regulatora przewodnictwa swoistego dla mukowiscydozy |
| 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 (OSRAM) | 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 |
| EP2555617A4 (en) * | 2010-04-05 | 2013-08-14 | Cadila Pharmaceuticals Ltd | NEW COMPOUNDS FOR THE TREATMENT OF HYPOGLYCEMIA |
| DK3150198T3 (da) | 2010-04-07 | 2021-11-01 | Vertex Pharma | Farmaceutiske sammensætninger af 3-(6-(1-(2,2-difluorbenzo[d][1,3]dioxol-5-yl)-cyclopropancarboxamido)-3-methylpyriodin-2-yl)benzoesyre og indgivelse deraf |
| RS54783B1 (sr) | 2010-04-07 | 2016-10-31 | Vertex Pharma | Čvrste forme 3-(6-(1-(2,2-difluorobenzo[d][1,3]dioksol-5-il)ciklopropankarboksiamido)-3-metilpiridin-2-il)benzoeve kiseline |
| CA2797118C (en) | 2010-04-22 | 2021-03-30 | Vertex Pharmaceuticals Incorporated | Process of producing cycloalkylcarboxamido-indole compounds |
| 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 |
| MX357328B (es) | 2011-11-08 | 2018-07-05 | Vertex Pharma | Moduladores de trasportadores de casete enlazante de atp. |
| AU2013226076B2 (en) | 2012-02-27 | 2017-11-16 | Vertex Pharmaceuticals Incorporated | Pharmaceutical composition and administration thereof |
| 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 |
| EP2872122A1 (en) | 2012-07-16 | 2015-05-20 | 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 |
| US10035801B2 (en) | 2013-03-13 | 2018-07-31 | Genentech, Inc. | Pyrazolo compounds and uses thereof |
| RU2718044C2 (ru) | 2013-11-12 | 2020-03-30 | Вертекс Фармасьютикалз Инкорпорейтед | Способ получения фармацевтических композиций для лечения опосредованных cftr заболеваний |
| RS62140B1 (sr) | 2014-04-15 | 2021-08-31 | Vertex Pharma | Farmaceutske kompozicije za lečenje bolesti posredovanih transmembranskim regulatorom provodljivosti cistične fibroze |
| KR20170063954A (ko) | 2014-10-07 | 2017-06-08 | 버텍스 파마슈티칼스 인코포레이티드 | 낭성 섬유증 막횡단 전도도 조절자의 조정제의 공-결정 |
| CN107077704B (zh) * | 2014-10-21 | 2021-12-03 | 埃森哲环球服务有限公司 | 用于针对微电网的容量确定的系统、方法以及装置以及有形计算机可读介质 |
| MX2017005663A (es) | 2014-10-31 | 2018-03-01 | Abbvie Sarl | Tetrahidropiranos sustituidos y metodo de uso. |
| HRP20211194T1 (hr) | 2014-11-18 | 2021-10-29 | Vertex Pharmaceuticals Inc. | Postupak za provođenje testova velike propusnosti putem tekućinske kromatografije visoke djelotvornosti |
| BR112017026132A2 (pt) | 2015-06-02 | 2018-08-28 | AbbVie S.à.r.l. | piridinas substituídas e métodos de uso |
| US9840513B2 (en) | 2015-07-16 | 2017-12-12 | Abbvie S.Á.R.L. | Substituted tricyclics and method of use |
| KR20180093882A (ko) | 2015-10-06 | 2018-08-22 | 프로테오스타시스 테라퓨틱스, 인크. | Cftr 조절용 화합물, 조성물, 및 방법 |
| US10130622B2 (en) | 2015-10-09 | 2018-11-20 | Abbvie S.Á.R.L. | Compounds for treatment of cystic fibrosis |
| EP3359539A1 (en) | 2015-10-09 | 2018-08-15 | AbbVie S.À.R.L. | Substituted pyrazolo[3,4-b]pyridin-6-carboxylic acids and their use |
| WO2017060874A1 (en) | 2015-10-09 | 2017-04-13 | Abbvie S.Á.R.L | N-sulfonylated pyrazolo[3,4-b]pyridin-6-carboxamides and method of use |
| 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 |
| US9981910B2 (en) | 2016-10-07 | 2018-05-29 | Abbvie S.Á.R.L. | Substituted pyrrolidines and methods of use |
| US10399940B2 (en) | 2016-10-07 | 2019-09-03 | Abbvie S.Á.R.L. | Substituted pyrrolidines and methods of use |
| WO2018116185A1 (en) | 2016-12-20 | 2018-06-28 | AbbVie S.à.r.l. | Deuterated cftr modulators and methods of use |
| TWI800498B (zh) * | 2016-12-21 | 2023-05-01 | 義大利商吉斯藥品公司 | 作為Rho-激酶抑制劑之雙環二氫嘧啶-羧醯胺衍生物 |
| 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 |
| JP2020533376A (ja) | 2017-09-15 | 2020-11-19 | アドゥロ バイオテック，インク． | ピラゾロピリミジノン化合物およびその使用 |
| 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 |
| US11236067B2 (en) | 2019-07-12 | 2022-02-01 | Orphomed, Inc. | Compound for treating cystic fibrosis |
| IL292965A (en) | 2019-11-12 | 2022-07-01 | Genzyme Corp | 6-membered heteroarylaminosulfonamides and methods of use |
| WO2021113809A1 (en) | 2019-12-05 | 2021-06-10 | Genzyme Corporation | Arylamides and methods of use thereof |
| WO2021113806A1 (en) | 2019-12-05 | 2021-06-10 | Genzyme Corporation | Arylamides and methods of use thereof |
| HUE069128T2 (hu) | 2019-12-06 | 2025-02-28 | Vertex Pharma | Szubsztituált tetrahidrofurán vegyületek mint nátriumcsatornák modulátorai |
| AR121356A1 (es) | 2020-02-18 | 2022-05-11 | Gilead Sciences Inc | Compuestos antivirales |
| TWI883391B (zh) | 2020-02-18 | 2025-05-11 | 美商基利科學股份有限公司 | 抗病毒化合物 |
| TWI874791B (zh) | 2020-02-18 | 2025-03-01 | 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 |
| JP2023547389A (ja) * | 2020-10-23 | 2023-11-10 | イルドン ファーマシューティカル カンパニー リミテッド | Ｃｆｔｒ調節剤化合物、その組成物及び用途 |
| US12324802B2 (en) | 2020-11-18 | 2025-06-10 | Vertex Pharmaceuticals Incorporated | Modulators of cystic fibrosis transmembrane conductance regulator |
| US20220213041A1 (en) | 2021-01-06 | 2022-07-07 | AbbVie Global Enterprises Ltd. | Modulators of the Cystic Fibrosis Transmembrane Conductance Regulator Protein and Methods of Use |
| EP4274828A1 (en) | 2021-01-06 | 2023-11-15 | 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 |
| AU2022284886A1 (en) | 2021-06-04 | 2023-11-30 | Vertex Pharmaceuticals Incorporated | N-(hydroxyalkyl (hetero)aryl) tetrahydrofuran carboxamides as modulators of sodium channels |
| CA3228162A1 (en) | 2021-08-18 | 2023-02-23 | Gilead Sciences, Inc. | Phospholipid compounds and methods of making and using the same |
| EP4396179A1 (en) | 2021-09-03 | 2024-07-10 | Genzyme Corporation | Indole compounds and methods of use |
| EP4396176A1 (en) | 2021-09-03 | 2024-07-10 | Genzyme Corporation | Indole compounds and uses thereof in the treatement of cystic fibrosis |
| AU2023338225A1 (en) | 2022-09-07 | 2025-03-20 | Genzyme Corporation | Macrocyclic compounds, compositions, and methods of using thereof |
| WO2024054851A1 (en) | 2022-09-07 | 2024-03-14 | Sionna Therapeutics | Macrocyclic compounds, compositions and methods of using thereof |
| WO2024054845A1 (en) | 2022-09-07 | 2024-03-14 | Sionna Therapeutics | Macrocycic 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 |
|---|---|---|---|---|
| US5420128A (en) | 1990-10-09 | 1995-05-30 | Otsuka Pharmaceutical Co., Ltd. | Pyrimidine derivatives, method of manufacturing the same, and androgen inhibitor |
| JP2003512379A (ja) * | 1999-10-15 | 2003-04-02 | ニューロクライン バイオサイエンシーズ， インコーポレイテッド | 性腺刺激ホルモン放出ホルモンレセプターアンタゴニストおよびそれに関連する方法 |
| NZ587549A (en) * | 2004-06-24 | 2012-10-26 | Vertex Pharma | 6-Amino-indole derivatives and processes for their preparation |
| JP5686596B2 (ja) * | 2007-05-25 | 2015-03-18 | 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Ｖｅｒｔｅｘ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃｏｒｐｏｒａｔｅｄ | 嚢胞性線維症膜貫通コンダクタンス制御因子の調節因子 |
| AU2008302598B2 (en) * | 2007-08-24 | 2014-07-17 | Vertex Pharmaceuticals Incorporated | Isothiazolopyridinones useful for the treatment of (inter alia) Cystic Fibrosis |
-
2008
- 2008-12-12 JP JP2010538183A patent/JP5637859B2/ja active Active
- 2008-12-12 EP EP08859265.4A patent/EP2231671B1/en active Active
- 2008-12-12 ES ES08859265T patent/ES2422741T3/es active Active
- 2008-12-12 CN CN2008801255937A patent/CN101925603B/zh not_active Expired - Fee Related
- 2008-12-12 NZ NZ586271A patent/NZ586271A/xx not_active IP Right Cessation
- 2008-12-12 CA CA2709301A patent/CA2709301C/en active Active
- 2008-12-12 WO PCT/US2008/086562 patent/WO2009076593A1/en not_active Ceased
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