JP2008542279A5 - - Google Patents
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- Publication number
- JP2008542279A5 JP2008542279A5 JP2008513583A JP2008513583A JP2008542279A5 JP 2008542279 A5 JP2008542279 A5 JP 2008542279A5 JP 2008513583 A JP2008513583 A JP 2008513583A JP 2008513583 A JP2008513583 A JP 2008513583A JP 2008542279 A5 JP2008542279 A5 JP 2008542279A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrimidine
- carboxamide
- phenyl
- optionally substituted
- piperidyl
- 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
- -1 carboxy, amino Chemical group 0.000 claims 77
- 150000001875 compounds Chemical class 0.000 claims 51
- 125000001072 heteroaryl group Chemical group 0.000 claims 27
- 125000000217 alkyl group Chemical group 0.000 claims 26
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 17
- 125000003710 aryl alkyl group Chemical group 0.000 claims 15
- 125000001931 aliphatic group Chemical group 0.000 claims 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims 12
- 239000000203 mixture Substances 0.000 claims 12
- 125000003118 aryl group Chemical group 0.000 claims 11
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 11
- 125000003107 substituted aryl group Chemical group 0.000 claims 11
- 125000001188 haloalkyl group Chemical group 0.000 claims 10
- 125000001475 halogen functional group Chemical group 0.000 claims 10
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 8
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 7
- AXDGFAKTACJXOG-UHFFFAOYSA-N 2-amino-6-(3-methoxyphenyl)pyrimidine-4-carboxamide Chemical compound COC1=CC=CC(C=2N=C(N)N=C(C=2)C(N)=O)=C1 AXDGFAKTACJXOG-UHFFFAOYSA-N 0.000 claims 6
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 6
- 125000002723 alicyclic group Chemical group 0.000 claims 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 6
- 125000003435 aroyl group Chemical group 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 6
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 4
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 4
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 4
- 125000002252 acyl group Chemical group 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims 4
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 3
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 3
- 108010006533 ATP-Binding Cassette Transporters Proteins 0.000 claims 3
- 102000005416 ATP-Binding Cassette Transporters Human genes 0.000 claims 3
- 241000124008 Mammalia Species 0.000 claims 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims 2
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 2
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 2
- 102000012605 Cystic Fibrosis Transmembrane Conductance Regulator Human genes 0.000 claims 2
- 108010079245 Cystic Fibrosis Transmembrane Conductance Regulator Proteins 0.000 claims 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical group C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 2
- 125000005126 aryl alkyl carbonyl amino group Chemical group 0.000 claims 2
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims 2
- 125000004104 aryloxy group Chemical group 0.000 claims 2
- 239000004202 carbamide Substances 0.000 claims 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 2
- 125000004181 carboxyalkyl group Chemical group 0.000 claims 2
- 125000005169 cycloalkylcarbonylamino group Chemical group 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000005224 heteroarylcarbonylamino group Chemical group 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- HKSQZEGSMBFHGC-UHFFFAOYSA-N pyrimidine-4-carboxamide Chemical compound NC(=O)C1=CC=NC=N1 HKSQZEGSMBFHGC-UHFFFAOYSA-N 0.000 claims 2
- 125000006413 ring segment Chemical group 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 2
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 2
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- NENLYAQPNATJSU-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline Chemical group C1NCCC2CCCCC21 NENLYAQPNATJSU-UHFFFAOYSA-N 0.000 claims 1
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 1
- BQSJMENFMHEYAS-UHFFFAOYSA-N 2-(3,4,4a,5,6,7,8,8a-octahydro-1h-isoquinolin-2-yl)-6-phenylpyrimidine-4-carboxamide Chemical compound N=1C(N2CC3CCCCC3CC2)=NC(C(=O)N)=CC=1C1=CC=CC=C1 BQSJMENFMHEYAS-UHFFFAOYSA-N 0.000 claims 1
- SUDVGHWNUQJVOX-UHFFFAOYSA-N 2-(cyclopropylmethylamino)-n-methyl-6-phenylpyrimidine-4-carboxamide Chemical compound N=1C(C(=O)NC)=CC(C=2C=CC=CC=2)=NC=1NCC1CC1 SUDVGHWNUQJVOX-UHFFFAOYSA-N 0.000 claims 1
- LORNOIPKRRASCE-UHFFFAOYSA-N 2-(diethylamino)-6-(2,3-dimethylphenyl)pyrimidine-4-carboxamide Chemical compound CCN(CC)C1=NC(C(N)=O)=CC(C=2C(=C(C)C=CC=2)C)=N1 LORNOIPKRRASCE-UHFFFAOYSA-N 0.000 claims 1
- VRJWKDMJSQKPCG-UHFFFAOYSA-N 2-(diethylamino)-6-(2,5-difluorophenyl)pyrimidine-4-carboxamide Chemical compound CCN(CC)C1=NC(C(N)=O)=CC(C=2C(=CC=C(F)C=2)F)=N1 VRJWKDMJSQKPCG-UHFFFAOYSA-N 0.000 claims 1
- NWQZFWPAVASWTO-UHFFFAOYSA-N 2-(diethylamino)-6-(2,6-difluorophenyl)pyrimidine-4-carboxamide Chemical compound CCN(CC)C1=NC(C(N)=O)=CC(C=2C(=CC=CC=2F)F)=N1 NWQZFWPAVASWTO-UHFFFAOYSA-N 0.000 claims 1
- GDDCNGFCFBHKAZ-UHFFFAOYSA-N 2-(diethylamino)-6-(3-fluorophenyl)pyrimidine-4-carboxamide Chemical compound CCN(CC)C1=NC(C(N)=O)=CC(C=2C=C(F)C=CC=2)=N1 GDDCNGFCFBHKAZ-UHFFFAOYSA-N 0.000 claims 1
- VEUSFFXYGRZSNW-UHFFFAOYSA-N 2-(diethylamino)-6-(4-ethylsulfonylphenyl)pyrimidine-4-carboxamide Chemical compound CCN(CC)C1=NC(C(N)=O)=CC(C=2C=CC(=CC=2)S(=O)(=O)CC)=N1 VEUSFFXYGRZSNW-UHFFFAOYSA-N 0.000 claims 1
- DTRZTUGMPYSMHJ-UHFFFAOYSA-N 2-(diethylamino)-6-(4-propan-2-ylphenyl)pyrimidine-4-carboxamide Chemical compound CCN(CC)C1=NC(C(N)=O)=CC(C=2C=CC(=CC=2)C(C)C)=N1 DTRZTUGMPYSMHJ-UHFFFAOYSA-N 0.000 claims 1
- NRKSVIFSXUJLGJ-UHFFFAOYSA-N 2-(diethylamino)-6-(5-fluoro-2-methoxyphenyl)pyrimidine-4-carboxamide Chemical compound CCN(CC)C1=NC(C(N)=O)=CC(C=2C(=CC=C(F)C=2)OC)=N1 NRKSVIFSXUJLGJ-UHFFFAOYSA-N 0.000 claims 1
- ZFHGMJCQSJWRGV-UHFFFAOYSA-N 2-(diethylamino)-6-(5-methylthiophen-2-yl)pyrimidine-4-carboxamide Chemical compound CCN(CC)C1=NC(C(N)=O)=CC(C=2SC(C)=CC=2)=N1 ZFHGMJCQSJWRGV-UHFFFAOYSA-N 0.000 claims 1
- OAXUFOBKVUIBIV-UHFFFAOYSA-N 2-(diethylamino)-n-methyl-6-phenylpyrimidine-4-carboxamide Chemical compound CCN(CC)C1=NC(C(=O)NC)=CC(C=2C=CC=CC=2)=N1 OAXUFOBKVUIBIV-UHFFFAOYSA-N 0.000 claims 1
- IMJDWBLJLUOJSX-UHFFFAOYSA-N 2-(ethylamino)-6-(3-methoxyphenyl)pyrimidine-4-carboxamide Chemical compound CCNC1=NC(C(N)=O)=CC(C=2C=C(OC)C=CC=2)=N1 IMJDWBLJLUOJSX-UHFFFAOYSA-N 0.000 claims 1
- WHMGPNKGYSREKA-UHFFFAOYSA-N 2-[4-(4-chlorobenzoyl)piperidin-1-yl]-6-phenylpyrimidine-4-carboxamide Chemical compound N=1C(C(=O)N)=CC(C=2C=CC=CC=2)=NC=1N(CC1)CCC1C(=O)C1=CC=C(Cl)C=C1 WHMGPNKGYSREKA-UHFFFAOYSA-N 0.000 claims 1
- OMDOKCWGQXQJAH-UHFFFAOYSA-N 2-[benzyl(ethyl)amino]-6-phenylpyrimidine-4-carboxamide Chemical compound N=1C(C(N)=O)=CC(C=2C=CC=CC=2)=NC=1N(CC)CC1=CC=CC=C1 OMDOKCWGQXQJAH-UHFFFAOYSA-N 0.000 claims 1
- NESAKYGLILEUHQ-UHFFFAOYSA-N 2-[bis(2-ethoxyethyl)amino]-6-phenylpyrimidine-4-carboxamide Chemical compound CCOCCN(CCOCC)C1=NC(C(N)=O)=CC(C=2C=CC=CC=2)=N1 NESAKYGLILEUHQ-UHFFFAOYSA-N 0.000 claims 1
- HVNWWWXFJGKMBO-UHFFFAOYSA-N 2-[butyl(2-hydroxyethyl)amino]-6-phenylpyrimidine-4-carboxamide Chemical compound CCCCN(CCO)C1=NC(C(N)=O)=CC(C=2C=CC=CC=2)=N1 HVNWWWXFJGKMBO-UHFFFAOYSA-N 0.000 claims 1
- KPMHGGYESQQHMM-UHFFFAOYSA-N 2-[butyl(cyanomethyl)amino]-6-phenylpyrimidine-4-carboxamide Chemical compound CCCCN(CC#N)C1=NC(C(N)=O)=CC(C=2C=CC=CC=2)=N1 KPMHGGYESQQHMM-UHFFFAOYSA-N 0.000 claims 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 1
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- 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 1
- VVLKNPIRSIWVOO-UHFFFAOYSA-N 6-phenyl-2-(4-propylpiperidin-1-yl)pyrimidine-4-carboxamide Chemical compound C1CC(CCC)CCN1C1=NC(C(N)=O)=CC(C=2C=CC=CC=2)=N1 VVLKNPIRSIWVOO-UHFFFAOYSA-N 0.000 claims 1
- FUYNLSIOABLYHR-UHFFFAOYSA-N 6-phenyl-2-pyrrolidin-1-ylpyrimidine-4-carboxamide Chemical compound N=1C(C(=O)N)=CC(C=2C=CC=CC=2)=NC=1N1CCCC1 FUYNLSIOABLYHR-UHFFFAOYSA-N 0.000 claims 1
- JEYPBSQMDUFGGB-UHFFFAOYSA-N C(C)N(C1=NC(=CC(=N1)C(=O)N)C1=CC(=CC=C1)OCC)CC.C(C)N(C1=NC(=CC(=N1)C(=O)N)C1=C(C=CC=C1OC)OC)CC Chemical compound C(C)N(C1=NC(=CC(=N1)C(=O)N)C1=CC(=CC=C1)OCC)CC.C(C)N(C1=NC(=CC(=N1)C(=O)N)C1=C(C=CC=C1OC)OC)CC JEYPBSQMDUFGGB-UHFFFAOYSA-N 0.000 claims 1
- WJESGGAGDMJBBM-UHFFFAOYSA-N C(C)N(C1=NC(=CC(=N1)C(=O)N)C1=CC=CC=C1)C.C1(CC1)CN(C1=NC(=CC(=N1)C(=O)N(C)C)C1=CC=CC=C1)CCC Chemical compound C(C)N(C1=NC(=CC(=N1)C(=O)N)C1=CC=CC=C1)C.C1(CC1)CN(C1=NC(=CC(=N1)C(=O)N(C)C)C1=CC=CC=C1)CCC WJESGGAGDMJBBM-UHFFFAOYSA-N 0.000 claims 1
- OEEOVFNIQFXDED-UHFFFAOYSA-N C1(=CC=CC=C1)C1=CC(=NC(=N1)N1CSCC1)C(=O)N.C(C)N(C1=NC(=CC(=N1)C(=O)N)C1=C(C=CC=C1)OC)CCO Chemical compound C1(=CC=CC=C1)C1=CC(=NC(=N1)N1CSCC1)C(=O)N.C(C)N(C1=NC(=CC(=N1)C(=O)N)C1=C(C=CC=C1)OC)CCO OEEOVFNIQFXDED-UHFFFAOYSA-N 0.000 claims 1
- IEAQSEBNYYBMSQ-UHFFFAOYSA-N C1(=CC=CC=C1)C1=CC(=NC(=N1)NCC#C)C(=O)N.C(C)N(C1=NC(=CC(=N1)C(=O)N)C1=C(C=C(C=C1)OC)OC)CC.C(CCCCC)N(C1=NC(=CC(=N1)C(=O)N)C1=CC=CC=C1)C Chemical compound C1(=CC=CC=C1)C1=CC(=NC(=N1)NCC#C)C(=O)N.C(C)N(C1=NC(=CC(=N1)C(=O)N)C1=C(C=C(C=C1)OC)OC)CC.C(CCCCC)N(C1=NC(=CC(=N1)C(=O)N)C1=CC=CC=C1)C IEAQSEBNYYBMSQ-UHFFFAOYSA-N 0.000 claims 1
- PXQMUYLHHUDPTG-UHFFFAOYSA-N C1(CC1)CN(C1=NC(=CC(=N1)C(=O)N)C1=CC(=CC=C1)OC)CCC.N1(CC=CC1)C(=O)C1=NC(=NC(=C1)C1=CC=CC=C1)N1CC=CC1 Chemical compound C1(CC1)CN(C1=NC(=CC(=N1)C(=O)N)C1=CC(=CC=C1)OC)CCC.N1(CC=CC1)C(=O)C1=NC(=NC(=C1)C1=CC=CC=C1)N1CC=CC1 PXQMUYLHHUDPTG-UHFFFAOYSA-N 0.000 claims 1
- LNRGVTZSROMRLS-UHFFFAOYSA-N CC1CN(CC(C1)C)C1=NC(=CC(=N1)C(=O)N)C1=CC=CC=C1.N1(CCC1)C1=NC(=CC(=N1)C(=O)N)C1=CC=CC=C1.CC1CN(CCC1)C1=NC(=CC(=N1)C(=O)N)C1=CC=CC=C1 Chemical compound CC1CN(CC(C1)C)C1=NC(=CC(=N1)C(=O)N)C1=CC=CC=C1.N1(CCC1)C1=NC(=CC(=N1)C(=O)N)C1=CC=CC=C1.CC1CN(CCC1)C1=NC(=CC(=N1)C(=O)N)C1=CC=CC=C1 LNRGVTZSROMRLS-UHFFFAOYSA-N 0.000 claims 1
- 241000065675 Cyclops Species 0.000 claims 1
- 201000003883 Cystic fibrosis Diseases 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 125000004652 decahydroisoquinolinyl group Chemical group C1(NCCC2CCCCC12)* 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims 1
- 125000001984 thiazolidinyl group Chemical group 0.000 claims 1
- 229930192474 thiophene Natural products 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- 0 *N(*=C)c1nc(/C2=C\C=C\C=C\C=C2)cc(C(N(*)O)=O)n1 Chemical compound *N(*=C)c1nc(/C2=C\C=C\C=C\C=C2)cc(C(N(*)O)=O)n1 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US68398205P | 2005-05-24 | 2005-05-24 | |
| US60/683,982 | 2005-05-24 | ||
| PCT/US2006/019712 WO2006127588A2 (en) | 2005-05-24 | 2006-05-22 | Modulators of atp-binding cassette transporters |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012229668A Division JP2013010800A (ja) | 2005-05-24 | 2012-10-17 | Ａｔｐ−結合カセットトランスポーターのモジュレーター |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008542279A JP2008542279A (ja) | 2008-11-27 |
| JP2008542279A5 true JP2008542279A5 (enExample) | 2009-07-02 |
| JP5426878B2 JP5426878B2 (ja) | 2014-02-26 |
Family
ID=37452684
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008513583A Expired - Fee Related JP5426878B2 (ja) | 2005-05-24 | 2006-05-22 | Ａｔｐ−結合カセットトランスポーターのモジュレーター |
| JP2012229668A Withdrawn JP2013010800A (ja) | 2005-05-24 | 2012-10-17 | Ａｔｐ−結合カセットトランスポーターのモジュレーター |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012229668A Withdrawn JP2013010800A (ja) | 2005-05-24 | 2012-10-17 | Ａｔｐ−結合カセットトランスポーターのモジュレーター |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8822451B2 (enExample) |
| EP (1) | EP1891018B1 (enExample) |
| JP (2) | JP5426878B2 (enExample) |
| CN (1) | CN101223146A (enExample) |
| AT (1) | ATE533749T1 (enExample) |
| AU (1) | AU2006251624A1 (enExample) |
| CA (1) | CA2609392A1 (enExample) |
| WO (1) | WO2006127588A2 (enExample) |
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| MXPA06002567A (es) | 2003-09-06 | 2006-09-04 | Vertex Pharma | Moduladores de transportadores con casete de union de atp. |
| RU2006120549A (ru) * | 2003-11-14 | 2007-12-27 | Вертекс Фармасьютикалз Инкорпорейтед (Us) | Тиазолы и оксазолы, применяемые в качестве модуляторов транспортеров арт-связывающей кассеты |
| US7977322B2 (en) | 2004-08-20 | 2011-07-12 | Vertex Pharmaceuticals Incorporated | Modulators of ATP-binding cassette transporters |
| CN101891680B (zh) | 2004-06-24 | 2014-10-29 | 沃泰克斯药物股份有限公司 | Atp-结合弹夹转运蛋白的调控剂 |
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| EP2774925B1 (en) | 2005-11-08 | 2016-12-28 | Vertex Pharmaceuticals Incorporated | Heterocyclic modulators of ATP-binding cassette transporters |
| AU2006331565A1 (en) * | 2005-12-27 | 2007-07-05 | Vertex Pharmaceuticals Incorporated | Compounds useful in CFTR assays and methods therewith |
| US7671221B2 (en) * | 2005-12-28 | 2010-03-02 | Vertex Pharmaceuticals Incorporated | Modulators of ATP-Binding Cassette transporters |
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| DK3219705T3 (da) | 2005-12-28 | 2020-04-14 | Vertex Pharma | Farmaceutiske sammensætninger af den amorfe form af n-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinolin-3-carboxamid |
| USRE50453E1 (en) | 2006-04-07 | 2025-06-10 | Vertex Pharmaceuticals Incorporated | Indole derivatives as CFTR modulators |
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| KR20100005730A (ko) | 2007-05-07 | 2010-01-15 | 노파르티스 아게 | 유기 화합물 |
| WO2008141119A2 (en) | 2007-05-09 | 2008-11-20 | Vertex Pharmaceuticals Incorporated | Modulators of cftr |
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| KR101123178B1 (ko) * | 2009-04-09 | 2012-06-13 | (주)에스메디 | 2-아릴벤조싸이오펜 유도체 또는 이의 약학적으로 허용가능한 염, 이의 제조방법 및 이를 유효성분으로 함유하는 퇴행성 뇌질환의 진단 또는 치료용 약학적 조성물 |
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| LT2826776T (lt) | 2010-03-25 | 2021-01-11 | Vertex Pharmaceuticals Incorporated | (r)-1(2,2-difluorbenzo(d)(1,3)dioksol-5-il)-n-(1-(2,3-dihidroksipropil)-6-fluor-2-(1-hidroksi-2-metilpropan-2-il)-1h-indol-5-il)-ciklopropankarboksamido kieta amorfinės formos dispersija |
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| US8372845B2 (en) | 2010-09-17 | 2013-02-12 | Novartis Ag | Pyrazine derivatives as enac blockers |
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| AU2012300567B2 (en) * | 2011-09-02 | 2016-03-10 | Purdue Pharma L.P. | Pyrimidines as sodium channel blockers |
| RU2640420C2 (ru) | 2011-11-08 | 2018-01-09 | Вертекс Фармасьютикалз Инкорпорейтед | Модуляторы транспортеров атф-связывающей кассеты |
| DE202011108486U1 (de) | 2011-11-30 | 2012-01-16 | Walter Beck | Fensteranschlussleiste |
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| JP2015511583A (ja) | 2012-02-27 | 2015-04-20 | 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 | 薬学的組成物およびその投与 |
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| SMT202500078T1 (it) | 2012-11-02 | 2025-03-12 | Vertex Pharma | Composizioni farmaceutiche per il trattamento di malattie mediate da cftr |
| HRP20210516T2 (hr) | 2013-11-12 | 2021-10-01 | Vertex Pharmaceuticals Incorporated | Postupak proizvodnje farmaceutskih pripravaka za liječenje bolesti koje su posredovane putem cftr |
| JP6543268B2 (ja) | 2014-04-15 | 2019-07-10 | 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 | 嚢胞性線維症膜コンダクタンス調節因子が媒介する疾患を処置するための医薬組成物 |
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| PT3551622T (pt) | 2016-12-09 | 2020-11-12 | Vertex Pharma | Modulador do regulador da condutância transmembrana da fibrose quística, composições farmacêuticas, métodos de tratamento e processo de fabrico do modulador |
| US11253509B2 (en) | 2017-06-08 | 2022-02-22 | Vertex Pharmaceuticals Incorporated | Methods of treatment for cystic fibrosis |
| WO2019018395A1 (en) | 2017-07-17 | 2019-01-24 | Vertex Pharmaceuticals Incorporated | METHODS OF TREATING CYSTIC FIBROSIS |
| TWI799435B (zh) | 2017-08-02 | 2023-04-21 | 美商維泰克斯製藥公司 | 製備化合物之製程 |
| US10654829B2 (en) | 2017-10-19 | 2020-05-19 | Vertex Pharmaceuticals Incorporated | Crystalline forms and compositions of CFTR modulators |
| CA3085006A1 (en) | 2017-12-08 | 2019-06-13 | Vertex Pharmaceuticals Incorporated | Processes for making modulators of cystic fibrosis transmembrane conductance regulator |
| TWI810243B (zh) | 2018-02-05 | 2023-08-01 | 美商維泰克斯製藥公司 | 用於治療囊腫纖化症之醫藥組合物 |
| US11414439B2 (en) | 2018-04-13 | 2022-08-16 | Vertex Pharmaceuticals Incorporated | Modulators of cystic fibrosis transmembrane conductance regulator, pharmaceutical compositions, methods of treatment, and process for making the modulator |
| EP3575287A1 (en) * | 2018-05-31 | 2019-12-04 | Universiteit Leiden | Inhibitors of n-acylphosphatidylethanolamine phospholipase d (nape-pld) |
| CR20230120A (es) | 2020-08-07 | 2023-09-01 | Vertex Pharma | Moduladores del regulador de la conductancia transmembrana de la fibrosis quística |
| US12324802B2 (en) | 2020-11-18 | 2025-06-10 | Vertex Pharmaceuticals Incorporated | Modulators of cystic fibrosis transmembrane conductance regulator |
| CN116354937B (zh) * | 2021-12-27 | 2025-07-11 | 江苏恩华药业股份有限公司 | 吡啶(嘧啶)胺类衍生物及其应用 |
| CN117624135A (zh) * | 2022-08-19 | 2024-03-01 | 德明药泰生物技术（深圳）有限公司 | 2-氮取代嘧啶类化合物及其制备方法和应用 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9909135D0 (en) * | 1999-04-22 | 1999-06-16 | Univ Wales Medicine | Cystic fibrosis medicaments |
| WO2002048148A2 (en) * | 2000-12-15 | 2002-06-20 | Glaxo Group Limited | Pyrazolopyridine derivatives |
| BR0212787A (pt) * | 2001-09-24 | 2005-01-25 | Elan Pharm Inc | Composto ou sal farmaceuticamente aceitável do mesmo, métodos de tratamento ou prevenção de doenças e de preparação de um composto, uso de um composto ou sal, e, composição farmacêutica |
| US20050113423A1 (en) | 2003-03-12 | 2005-05-26 | Vangoor Frederick F. | Modulators of ATP-binding cassette transporters |
| WO2004087679A1 (en) | 2003-04-01 | 2004-10-14 | Aponetics Ag | 2, 4, 6-trisubstituted pyrimidine derivatives useful for the treatment of neoplastic and autoimmune diseases |
| MXPA06002567A (es) * | 2003-09-06 | 2006-09-04 | Vertex Pharma | Moduladores de transportadores con casete de union de atp. |
| GB0403155D0 (en) | 2004-02-12 | 2004-03-17 | Vernalis Res Ltd | Chemical compounds |
| WO2005113514A2 (en) * | 2004-05-07 | 2005-12-01 | Janssen Pharmaceutica, N.V. | Substituted pyrimidines as inhibitors of bacterial type iii protein secretion systems |
-
2006
- 2006-05-22 JP JP2008513583A patent/JP5426878B2/ja not_active Expired - Fee Related
- 2006-05-22 AU AU2006251624A patent/AU2006251624A1/en not_active Abandoned
- 2006-05-22 CA CA002609392A patent/CA2609392A1/en not_active Abandoned
- 2006-05-22 WO PCT/US2006/019712 patent/WO2006127588A2/en not_active Ceased
- 2006-05-22 AT AT06770825T patent/ATE533749T1/de active
- 2006-05-22 US US11/438,636 patent/US8822451B2/en active Active
- 2006-05-22 EP EP06770825A patent/EP1891018B1/en not_active Expired - Lifetime
- 2006-05-22 CN CNA2006800258695A patent/CN101223146A/zh active Pending
-
2012
- 2012-10-17 JP JP2012229668A patent/JP2013010800A/ja not_active Withdrawn
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