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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| 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 |
| CA2810655C (en) | 2004-06-24 | 2013-12-10 | Vertex Pharmaceuticals Incorporated | Modulators of atp-binding cassette transporters |
| EP1912983B1 (en) | 2005-08-11 | 2011-06-08 | Vertex Pharmaceuticals, Inc. | Modulators of cystic fibrosis transmembrane conductance regulator |
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| CA2635214A1 (en) * | 2005-12-27 | 2007-07-05 | Vertex Pharmaceuticals Incorporated | Compounds useful in cftr assays and methods therewith |
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| RS55940B1 (sr) | 2005-12-28 | 2017-09-29 | Vertex Pharma | Čvrsti oblici n-[2,4-bis(1,1-dimetiletil)-5-hidroksifenil]-1,4-dihidro-4-oksohinolin-3-karboksamida |
| US7671221B2 (en) * | 2005-12-28 | 2010-03-02 | Vertex Pharmaceuticals Incorporated | Modulators of ATP-Binding Cassette transporters |
| HUE036165T2 (hu) | 2006-04-07 | 2018-06-28 | Vertex Pharma | ATP-kötõ kazetta transzportereinek modulátorai |
| USRE50453E1 (en) | 2006-04-07 | 2025-06-10 | Vertex Pharmaceuticals Incorporated | Indole derivatives as CFTR modulators |
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| US10022352B2 (en) | 2006-04-07 | 2018-07-17 | Vertex Pharmaceuticals Incorporated | Modulators of ATP-binding cassette transporters |
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| KR20100005730A (ko) | 2007-05-07 | 2010-01-15 | 노파르티스 아게 | 유기 화합물 |
| AU2008251504B2 (en) | 2007-05-09 | 2013-07-18 | Vertex Pharmaceuticals Incorporated | Modulators of CFTR |
| HUE028426T2 (en) | 2007-08-24 | 2016-12-28 | Vertex Pharma | Isothiazolopyridinones for (inter alia) treating cystic fibrosis |
| EP2065381A1 (de) | 2007-10-18 | 2009-06-03 | Boehringer Ingelheim Pharma GmbH & Co. KG | CGRP Antagonisten |
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| PT2217572E (pt) | 2007-11-16 | 2014-02-17 | Vertex Pharma | Moduladores de isoquinolina de transportadores de cassete de ligação a atp |
| CA2705405A1 (en) * | 2007-11-22 | 2009-05-28 | Boehringer Ingelheim International Gmbh | New compounds |
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| KR20100098545A (ko) * | 2007-12-07 | 2010-09-07 | 버텍스 파마슈티칼스 인코포레이티드 | ３（６（１２,２디플루오로벤조〔ｄ〕〔１,３〕디옥솔５일）사이클로프로판카복스아미도）３메틸피리딘２일）벤조산의 제형 |
| NZ585880A (en) | 2007-12-07 | 2012-08-31 | Vertex Pharma | Solid forms of 3-(6-(1-(2,2-difluorobenzo[d][1,3] dioxol-5-yl) cyclopropanecarboxamido)-3-methylpyridin-2-yl) benzoic acid |
| HUE029775T2 (en) | 2007-12-07 | 2017-04-28 | Vertex Pharma | Process for the preparation of cycloalkylcarboxamido pyridine benzoic acids |
| EA017919B1 (ru) | 2007-12-10 | 2013-04-30 | Новартис Аг | Производные пиразин-2-карбоксамида для лечения заболеваний, которые поддаются лечению путем блокирования эпителиальных натриевых каналов |
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| PT2615085E (pt) | 2008-03-31 | 2015-10-09 | Vertex Pharma | Derivados piridilo como moduladores cftr |
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| 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 |
| CN102164587A (zh) | 2008-09-29 | 2011-08-24 | 沃泰克斯药物股份有限公司 | 3-(6-(1-(2,2-二氟苯并[d][1,3]间二氧杂环戊烯-5-基)环丙烷甲酰氨基)-3-甲基吡啶-2-基)苯甲酸的剂量单元 |
| NZ592685A (en) | 2008-10-23 | 2013-04-26 | Vertex Pharma | Modulators of cystic fibrosis transmembrane conductance regulator |
| US8513242B2 (en) | 2008-12-12 | 2013-08-20 | Cystic Fibrosis Foundation Therapeutics, Inc. | Pyrimidine compounds and methods of making and using same |
| SG193156A1 (en) | 2009-03-20 | 2013-09-30 | Vertex Pharma | Process for making modulators of cystic fibrosis transmembrane conductance regulator |
| 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 |
| WO2011050325A1 (en) | 2009-10-22 | 2011-04-28 | Vertex Pharmaceuticals Incorporated | Compositions for treatment of cystic fibrosis and other chronic diseases |
| ES2604105T3 (es) | 2010-03-25 | 2017-03-03 | Vertex Pharmaceuticals Incorporated | Formula cristalina de (r) -1 (2,2- difluorobenzo [d] [1,3] dioxol - 5yl) - n- (1- (2,3 - dihidroxipropil) - 6 - fluoro - 2- (1 - hydroxy-2-metilpropan-2il) -1h-indol-5il) cyclopropanecarboxamida |
| 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 |
| EP2555754B1 (en) | 2010-04-07 | 2016-04-06 | Vertex Pharmaceuticals Incorporated | Solid forms of 3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl) cyclopropanecarboxamido)-3-methylpyridin-2-yl)benzoic acid |
| EP3150198B1 (en) | 2010-04-07 | 2021-09-22 | Vertex Pharmaceuticals Incorporated | Pharmaceutical compositions of 3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl) cyclopropanecarboxamido)-3-methylpyriodin-2-yl)benzoic acid and administration thereof |
| SG10201505700QA (en) | 2010-04-22 | 2015-08-28 | Vertex Pharma | 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 |
| BR112013004443A8 (pt) | 2010-08-23 | 2018-01-02 | Vertex Pharma | composições farmacêuticas de (r)-1-(2,2-difluorbenzo[d] [1,3]dioxol-5-il)-n-(1-(2,3-di-hidróxipropil)-6-flúor-2-(1-hidróxi-2-metilpropan-2-il)-1h-indol-5-il)ciclopropano carboxamida e administração das mesmas |
| US8372845B2 (en) | 2010-09-17 | 2013-02-12 | Novartis Ag | Pyrazine derivatives as enac blockers |
| US8685993B2 (en) | 2010-12-21 | 2014-04-01 | Novartis Ag | Bi-heteroaryl compounds as Vps34 inhibitors |
| HRP20171389T1 (hr) | 2011-09-02 | 2017-11-03 | Purdue Pharma Lp | Pirimidini kao blokatori natrijevog kanala |
| ES2622154T3 (es) | 2011-11-08 | 2017-07-05 | Vertex Pharmaceuticals Incorporated | Moduladores de transportadores de cassete de unión atp-binding |
| DE202011108486U1 (de) | 2011-11-30 | 2012-01-16 | Walter Beck | Fensteranschlussleiste |
| HK1199205A1 (en) | 2012-01-25 | 2015-06-26 | 沃泰克斯药物股份有限公司 | Formulations of 3-(6-(1-(2.2-difluorobenzo[d][1,3]dioxol-5-yl) cyclopropanecarboxamido)-3-methylpyridin-2-yl)benzoic acid |
| BR112014021090B1 (pt) | 2012-02-27 | 2023-01-24 | Vertex Pharmaceuticals Incorporated | Composição farmacêutica e uso de n-[2,4-bis(1,1-dimetiletil)-5-hidróxifenil]-1,4-di-hidro-4-oxoquinolina3-carboxamida na preparação da mesma |
| US8809340B2 (en) | 2012-03-19 | 2014-08-19 | Novartis Ag | Crystalline form |
| 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 |
| WO2014005084A1 (en) | 2012-06-29 | 2014-01-03 | Lixte Biotechnology, Inc. | Oxabicycloheptanes and oxabicycloheptenes for the treatment of diabetes |
| AR092857A1 (es) | 2012-07-16 | 2015-05-06 | Vertex Pharma | Composiciones farmaceuticas de (r)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-il)-n-(1-(2,3-dihidroxipropil)-6-fluoro-2-(1-hidroxi-2-metilpropan-2-il)-1h-indol-5-il)ciclopropancarboxamida y administracion de las mismas |
| WO2014071122A1 (en) | 2012-11-02 | 2014-05-08 | Vertex Pharmaceuticals Incorporated | Pharmaceutical compositions for the treatment of cftr mediated diseases |
| EP3068392B9 (en) | 2013-11-12 | 2021-08-04 | Vertex Pharmaceuticals Incorporated | Process of preparing pharmaceutical compositions for the treatment of cftr mediated diseases |
| CA2944140C (en) | 2014-04-15 | 2022-10-04 | Vertex Pharmaceuticals Incorporated | Pharmaceutical compositions for the treatment of cystic fibrosis transmembrane conductance regulator mediated diseases |
| DK3203840T3 (da) | 2014-10-06 | 2020-08-31 | Vertex Pharma | Modulatorer af cystisk fibrose-transmembrankonduktansregulator |
| EP3204358B1 (en) | 2014-10-07 | 2018-09-19 | Vertex Pharmaceuticals Incorporated | Co-crystals of modulators of cystic fibrosis transmembrane conductance regulator |
| US10302602B2 (en) | 2014-11-18 | 2019-05-28 | Vertex Pharmaceuticals Incorporated | Process of conducting high throughput testing high performance liquid chromatography |
| MD3551622T2 (ro) | 2016-12-09 | 2021-03-31 | Vertex Pharma | Modulator al regulatorului conductanței transmembranare în fibroză chistică, compoziții farmaceutice, metode de tratament și procedeu pentru fabricarea modulatorului |
| WO2018227049A1 (en) | 2017-06-08 | 2018-12-13 | Vertex Pharmaceuticals Incorporated | Methods of treatment for cystic fibrosis |
| MA49631A (fr) | 2017-07-17 | 2020-05-27 | Vertex Pharma | Méthodes de traitement de la fibrose kystique |
| ES2912657T3 (es) | 2017-08-02 | 2022-05-26 | Vertex Pharma | Procesos para preparar compuestos de pirrolidina |
| MA50400A (fr) | 2017-10-19 | 2020-08-26 | Vertex Pharma | Formes cristallines et compositions de modulateurs de cftr |
| US11465985B2 (en) | 2017-12-08 | 2022-10-11 | 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 |
| EP3774825A1 (en) | 2018-04-13 | 2021-02-17 | 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 |
| EP1377573B1 (en) * | 2000-12-15 | 2005-07-27 | Glaxo Group Limited | Pyrazolopyridine derivatives |
| MXPA04002785A (es) * | 2001-09-24 | 2004-07-29 | Elan Pharm Inc | Aminas sustituidas para tratamiento de enfermedad de alzheimer. |
| EP1601657A1 (en) * | 2003-03-12 | 2005-12-07 | Vertex Pharmaceuticals Incorporated | Pyrazole modulators of atp-binding cassette transporters |
| EP1644338A1 (en) | 2003-04-01 | 2006-04-12 | Aponetics AG | 2, 4, 6-trisubstituted pyrimidine derivatives useful for the treatment of neoplastic and autoimmune diseases |
| WO2005026137A2 (en) * | 2003-09-06 | 2005-03-24 | Vertex Pharmaceuticals Incorporated | Modulators of atp-binding cassette transporters |
| 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 US US11/438,636 patent/US8822451B2/en active Active
- 2006-05-22 EP EP06770825A patent/EP1891018B1/en not_active Not-in-force
- 2006-05-22 WO PCT/US2006/019712 patent/WO2006127588A2/en not_active Ceased
- 2006-05-22 JP JP2008513583A patent/JP5426878B2/ja not_active Expired - Fee Related
- 2006-05-22 CA CA002609392A patent/CA2609392A1/en not_active Abandoned
- 2006-05-22 AT AT06770825T patent/ATE533749T1/de active
- 2006-05-22 AU AU2006251624A patent/AU2006251624A1/en not_active Abandoned
- 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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