JP2007503443A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2007503443A5 JP2007503443A5 JP2006524755A JP2006524755A JP2007503443A5 JP 2007503443 A5 JP2007503443 A5 JP 2007503443A5 JP 2006524755 A JP2006524755 A JP 2006524755A JP 2006524755 A JP2006524755 A JP 2006524755A JP 2007503443 A5 JP2007503443 A5 JP 2007503443A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridyl
- xanthine
- alkyl
- dipropyl
- aryl
- 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
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 claims 119
- 229940075420 xanthine Drugs 0.000 claims 62
- 150000001875 compounds Chemical class 0.000 claims 51
- -1 which is optionally Chemical group 0.000 claims 46
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 36
- 239000001257 hydrogen Substances 0.000 claims 32
- 229910052739 hydrogen Inorganic materials 0.000 claims 32
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 30
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 20
- 125000005843 halogen group Chemical group 0.000 claims 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 15
- 150000002431 hydrogen Chemical group 0.000 claims 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims 14
- 125000000623 heterocyclic group Chemical group 0.000 claims 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 14
- 125000001072 heteroaryl group Chemical group 0.000 claims 13
- 125000001424 substituent group Chemical group 0.000 claims 13
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 12
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 11
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 10
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 10
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 10
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 10
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 10
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 8
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims 8
- 125000003342 alkenyl group Chemical group 0.000 claims 8
- 125000000304 alkynyl group Chemical group 0.000 claims 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 4
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 4
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 3
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 3
- 150000001412 amines Chemical class 0.000 claims 3
- 125000002785 azepinyl group Chemical group 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
- 125000002576 diazepinyl group Chemical group N1N=C(C=CC=C1)* 0.000 claims 3
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
- 125000006178 methyl benzyl group Chemical group 0.000 claims 3
- 125000002757 morpholinyl group Chemical group 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 3
- 125000004193 piperazinyl group Chemical group 0.000 claims 3
- 125000005936 piperidyl group Chemical group 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 125000006413 ring segment Chemical group 0.000 claims 3
- 125000001544 thienyl group Chemical group 0.000 claims 3
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 3
- MDNORVBNPKBWBW-UHFFFAOYSA-N 1,3-diethyl-8-[6-(2-pyrrolidin-1-ylethylamino)pyridin-3-yl]-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CC)C(=O)N(CC)C=2N=C1C(C=N1)=CC=C1NCCN1CCCC1 MDNORVBNPKBWBW-UHFFFAOYSA-N 0.000 claims 2
- WPHTUXVYLNYAPA-UHFFFAOYSA-N 1,3-diethyl-8-[6-(pyridin-2-ylmethylamino)pyridin-3-yl]-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CC)C(=O)N(CC)C=2N=C1C(C=N1)=CC=C1NCC1=CC=CC=N1 WPHTUXVYLNYAPA-UHFFFAOYSA-N 0.000 claims 2
- ACPCSLMZOHRHCS-UHFFFAOYSA-N 1,3-diethyl-8-[6-(pyridin-3-ylmethylamino)pyridin-3-yl]-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CC)C(=O)N(CC)C=2N=C1C(C=N1)=CC=C1NCC1=CC=CN=C1 ACPCSLMZOHRHCS-UHFFFAOYSA-N 0.000 claims 2
- AMLDMLKJJSTZMK-UHFFFAOYSA-N 1,3-diethyl-8-[6-[(3-methoxyphenyl)methylamino]pyridin-3-yl]-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CC)C(=O)N(CC)C=2N=C1C(C=N1)=CC=C1NCC1=CC=CC(OC)=C1 AMLDMLKJJSTZMK-UHFFFAOYSA-N 0.000 claims 2
- WOKWGMFNGCZRJL-UHFFFAOYSA-N 1,3-dimethyl-8-[6-(methylamino)pyridin-3-yl]-7h-purine-2,6-dione Chemical compound C1=NC(NC)=CC=C1C(N1)=NC2=C1C(=O)N(C)C(=O)N2C WOKWGMFNGCZRJL-UHFFFAOYSA-N 0.000 claims 2
- ZPFNEXUPYQUHEN-UHFFFAOYSA-N 1,3-dipropyl-8-(6-pyrrolidin-1-ylpyridin-3-yl)-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C(C=N1)=CC=C1N1CCCC1 ZPFNEXUPYQUHEN-UHFFFAOYSA-N 0.000 claims 2
- YXKJPXVMZWGIBI-UHFFFAOYSA-N 1,3-dipropyl-8-[6-(2-pyridin-2-ylethylamino)pyridin-3-yl]-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C(C=N1)=CC=C1NCCC1=CC=CC=N1 YXKJPXVMZWGIBI-UHFFFAOYSA-N 0.000 claims 2
- RTYAAMZBWVNQHX-UHFFFAOYSA-N 1-[5-(1,3-diethyl-2,6-dioxo-7h-purin-8-yl)pyridin-2-yl]-1-(2-methoxyethyl)-3-pyridin-4-ylurea Chemical compound N1C=2C(=O)N(CC)C(=O)N(CC)C=2N=C1C(C=N1)=CC=C1N(CCOC)C(=O)NC1=CC=NC=C1 RTYAAMZBWVNQHX-UHFFFAOYSA-N 0.000 claims 2
- LFXCYVITBNVTHL-UHFFFAOYSA-N 8-(6-chloropyridin-3-yl)-1,3-dipropyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C1=CC=C(Cl)N=C1 LFXCYVITBNVTHL-UHFFFAOYSA-N 0.000 claims 2
- OJWDYRZKBKCUAP-UHFFFAOYSA-N 8-(6-morpholin-4-ylpyridin-3-yl)-1,3-dipropyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C(C=N1)=CC=C1N1CCOCC1 OJWDYRZKBKCUAP-UHFFFAOYSA-N 0.000 claims 2
- YITUHJOCTFWXRO-UHFFFAOYSA-N 8-(6-piperazin-1-ylpyridin-3-yl)-1,3-dipropyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C(C=N1)=CC=C1N1CCNCC1 YITUHJOCTFWXRO-UHFFFAOYSA-N 0.000 claims 2
- CCOGRGCHXAXCLY-UHFFFAOYSA-N 8-[6-(1-hydroxypropan-2-ylamino)pyridin-3-yl]-1,3-dipropyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C1=CC=C(NC(C)CO)N=C1 CCOGRGCHXAXCLY-UHFFFAOYSA-N 0.000 claims 2
- YEYAJHKHEQLJSU-UHFFFAOYSA-N 8-[6-(2,2-dimethoxyethylamino)pyridin-3-yl]-1,3-dipropyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C1=CC=C(NCC(OC)OC)N=C1 YEYAJHKHEQLJSU-UHFFFAOYSA-N 0.000 claims 2
- DSEIFWOSOXXVCQ-UHFFFAOYSA-N 8-[6-(2-hydroxyethylamino)pyridin-3-yl]-1,3-dipropyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C1=CC=C(NCCO)N=C1 DSEIFWOSOXXVCQ-UHFFFAOYSA-N 0.000 claims 2
- LUNHWMIOHDKVMI-UHFFFAOYSA-N 8-[6-(2-hydroxypropylamino)pyridin-3-yl]-1,3-dipropyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C1=CC=C(NCC(C)O)N=C1 LUNHWMIOHDKVMI-UHFFFAOYSA-N 0.000 claims 2
- JUYSXFPGBMZVFU-UHFFFAOYSA-N 8-[6-(4-acetylpiperazin-1-yl)pyridin-3-yl]-1,3-dipropyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C(C=N1)=CC=C1N1CCN(C(C)=O)CC1 JUYSXFPGBMZVFU-UHFFFAOYSA-N 0.000 claims 2
- XTETXCDXUFUPRO-UHFFFAOYSA-N 8-[6-(4-methyl-1,4-diazepan-1-yl)pyridin-3-yl]-1,3-dipropyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C(C=N1)=CC=C1N1CCCN(C)CC1 XTETXCDXUFUPRO-UHFFFAOYSA-N 0.000 claims 2
- KVBOVZQWQICWQI-UHFFFAOYSA-N 8-[6-(dimethylamino)pyridin-3-yl]-1,3-dipropyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C1=CC=C(N(C)C)N=C1 KVBOVZQWQICWQI-UHFFFAOYSA-N 0.000 claims 2
- ZRJNXCPEVPTJAO-UHFFFAOYSA-N 8-[6-(ethylamino)pyridin-3-yl]-1,3-dipropyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C1=CC=C(NCC)N=C1 ZRJNXCPEVPTJAO-UHFFFAOYSA-N 0.000 claims 2
- UZVULRPRIUSGOU-UHFFFAOYSA-N 8-[6-(methylamino)pyridin-3-yl]-1,3-dipropyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C1=CC=C(NC)N=C1 UZVULRPRIUSGOU-UHFFFAOYSA-N 0.000 claims 2
- KUDCJUNZZJSTFH-UHFFFAOYSA-N 8-[6-[[4-(aminomethyl)phenyl]methylamino]pyridin-3-yl]-1,3-dipropyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C(C=N1)=CC=C1NCC1=CC=C(CN)C=C1 KUDCJUNZZJSTFH-UHFFFAOYSA-N 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 125000000753 cycloalkyl 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
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- GOKQVWBBFBOYQL-UHFFFAOYSA-N n-[2-[[5-(2,6-dioxo-1,3-dipropyl-7h-purin-8-yl)pyridin-2-yl]amino]ethyl]acetamide Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C1=CC=C(NCCNC(C)=O)N=C1 GOKQVWBBFBOYQL-UHFFFAOYSA-N 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 125000005592 polycycloalkyl group Polymers 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 125000004306 triazinyl group Chemical group 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- 125000006719 (C6-C10) aryl (C1-C6) alkyl group Chemical group 0.000 claims 1
- IFLFELZCFXQLGN-UHFFFAOYSA-N 1,3-bis(cyclopropylmethyl)-8-[6-(methylamino)pyridin-3-yl]-7h-purine-2,6-dione Chemical compound C1=NC(NC)=CC=C1C(N1)=NC2=C1C(=O)N(CC1CC1)C(=O)N2CC1CC1 IFLFELZCFXQLGN-UHFFFAOYSA-N 0.000 claims 1
- DFKVQPMXXSMIRH-UHFFFAOYSA-N 1,3-diethyl-8-(6-hydrazinylpyridin-3-yl)-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CC)C(=O)N(CC)C=2N=C1C1=CC=C(NN)N=C1 DFKVQPMXXSMIRH-UHFFFAOYSA-N 0.000 claims 1
- FXFOPWFQZYTBGQ-UHFFFAOYSA-N 1,3-diethyl-8-(6-piperazin-1-ylpyridin-3-yl)-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CC)C(=O)N(CC)C=2N=C1C(C=N1)=CC=C1N1CCNCC1 FXFOPWFQZYTBGQ-UHFFFAOYSA-N 0.000 claims 1
- JDAIIBVBMKHMRV-UHFFFAOYSA-N 1,3-diethyl-8-(6-pyrrolidin-1-ylpyridin-3-yl)-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CC)C(=O)N(CC)C=2N=C1C(C=N1)=CC=C1N1CCCC1 JDAIIBVBMKHMRV-UHFFFAOYSA-N 0.000 claims 1
- YEVKMLIRPXIILD-UHFFFAOYSA-N 1,3-diethyl-8-[6-(2-methoxyethylamino)pyridin-3-yl]-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CC)C(=O)N(CC)C=2N=C1C1=CC=C(NCCOC)N=C1 YEVKMLIRPXIILD-UHFFFAOYSA-N 0.000 claims 1
- KDVJCOVCCHYLAN-UHFFFAOYSA-N 1,3-diethyl-8-[6-(2-pyridin-2-ylethylamino)pyridin-3-yl]-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CC)C(=O)N(CC)C=2N=C1C(C=N1)=CC=C1NCCC1=CC=CC=N1 KDVJCOVCCHYLAN-UHFFFAOYSA-N 0.000 claims 1
- FNXANIKDBCUJFU-UHFFFAOYSA-N 1,3-diethyl-8-[6-(2-pyridin-3-ylethylamino)pyridin-3-yl]-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CC)C(=O)N(CC)C=2N=C1C(C=N1)=CC=C1NCCC1=CC=CN=C1 FNXANIKDBCUJFU-UHFFFAOYSA-N 0.000 claims 1
- ZAKSGVNUQDLKJI-UHFFFAOYSA-N 1,3-diethyl-8-[6-(4-pyridin-2-ylpiperazin-1-yl)pyridin-3-yl]-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CC)C(=O)N(CC)C=2N=C1C(C=N1)=CC=C1N(CC1)CCN1C1=CC=CC=N1 ZAKSGVNUQDLKJI-UHFFFAOYSA-N 0.000 claims 1
- GFQZJFIWUWHPKK-UHFFFAOYSA-N 1,3-diethyl-8-[6-(ethylamino)pyridin-3-yl]-7h-purine-2,6-dione Chemical compound C1=NC(NCC)=CC=C1C(N1)=NC2=C1C(=O)N(CC)C(=O)N2CC GFQZJFIWUWHPKK-UHFFFAOYSA-N 0.000 claims 1
- SDOISGYXPAHLCT-UHFFFAOYSA-N 1,3-diethyl-8-[6-(methylamino)pyridin-3-yl]-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CC)C(=O)N(CC)C=2N=C1C1=CC=C(NC)N=C1 SDOISGYXPAHLCT-UHFFFAOYSA-N 0.000 claims 1
- BFZQIWAAJMDUHH-UHFFFAOYSA-N 1,3-dipropyl-8-[6-(2-pyridin-3-ylethylamino)pyridin-3-yl]-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C(C=N1)=CC=C1NCCC1=CC=CN=C1 BFZQIWAAJMDUHH-UHFFFAOYSA-N 0.000 claims 1
- DHFBNIRKDALHDN-UHFFFAOYSA-N 1,3-dipropyl-8-[6-(4-pyridin-2-ylpiperazin-1-yl)pyridin-3-yl]-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C(C=N1)=CC=C1N(CC1)CCN1C1=CC=CC=N1 DHFBNIRKDALHDN-UHFFFAOYSA-N 0.000 claims 1
- PQUQIZKVWHSREO-UHFFFAOYSA-N 1,3-dipropyl-8-[6-(propylamino)pyridin-3-yl]-7h-purine-2,6-dione Chemical compound C1=NC(NCCC)=CC=C1C(N1)=NC2=C1C(=O)N(CCC)C(=O)N2CCC PQUQIZKVWHSREO-UHFFFAOYSA-N 0.000 claims 1
- SDNNLUOKPWUNIE-UHFFFAOYSA-N 1,3-dipropyl-8-[6-(pyridin-2-ylmethylamino)pyridin-3-yl]-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C(C=N1)=CC=C1NCC1=CC=CC=N1 SDNNLUOKPWUNIE-UHFFFAOYSA-N 0.000 claims 1
- VHBNSKSUZNEIKN-UHFFFAOYSA-N 1,3-dipropyl-8-[6-(pyridin-3-ylmethylamino)pyridin-3-yl]-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C(C=N1)=CC=C1NCC1=CC=CN=C1 VHBNSKSUZNEIKN-UHFFFAOYSA-N 0.000 claims 1
- NJDFVPQFAZZGCD-UHFFFAOYSA-N 1,3-dipropyl-8-[6-(pyridin-4-ylamino)pyridin-3-yl]-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C(C=N1)=CC=C1NC1=CC=NC=C1 NJDFVPQFAZZGCD-UHFFFAOYSA-N 0.000 claims 1
- UKRMBINNGLSNTR-UHFFFAOYSA-N 1,3-dipropyl-8-[6-(thiophen-2-ylmethylamino)pyridin-3-yl]-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C(C=N1)=CC=C1NCC1=CC=CS1 UKRMBINNGLSNTR-UHFFFAOYSA-N 0.000 claims 1
- URSMMEIGUOXILT-UHFFFAOYSA-N 1-(cyclopropylmethyl)-3-ethyl-8-[6-(methylamino)pyridin-3-yl]-7h-purine-2,6-dione Chemical compound O=C1N(CC)C=2N=C(C=3C=NC(NC)=CC=3)NC=2C(=O)N1CC1CC1 URSMMEIGUOXILT-UHFFFAOYSA-N 0.000 claims 1
- KQUAXDUORCKXRU-UHFFFAOYSA-N 1-cyclopropyl-3-ethyl-8-[6-(methylamino)pyridin-3-yl]-7h-purine-2,6-dione Chemical compound O=C1N(CC)C=2N=C(C=3C=NC(NC)=CC=3)NC=2C(=O)N1C1CC1 KQUAXDUORCKXRU-UHFFFAOYSA-N 0.000 claims 1
- HXKWXZFMPSMNLP-UHFFFAOYSA-N 1-cyclopropyl-8-[6-(2-methoxyethylamino)pyridin-3-yl]-3-propyl-7h-purine-2,6-dione Chemical compound O=C1N(CCC)C=2N=C(C=3C=NC(NCCOC)=CC=3)NC=2C(=O)N1C1CC1 HXKWXZFMPSMNLP-UHFFFAOYSA-N 0.000 claims 1
- CPAFOHDUXCUDBQ-UHFFFAOYSA-N 1-cyclopropyl-8-[6-(methylamino)pyridin-3-yl]-3-propyl-7h-purine-2,6-dione Chemical compound O=C1N(CCC)C=2N=C(C=3C=NC(NC)=CC=3)NC=2C(=O)N1C1CC1 CPAFOHDUXCUDBQ-UHFFFAOYSA-N 0.000 claims 1
- OOQFDAKIXHLFBN-UHFFFAOYSA-N 3-(2-methoxy-2-phenylethyl)-8-(6-piperazin-1-ylpyridin-3-yl)-1-propyl-7h-purine-2,6-dione Chemical compound C1=2N=C(C=3C=NC(=CC=3)N3CCNCC3)NC=2C(=O)N(CCC)C(=O)N1CC(OC)C1=CC=CC=C1 OOQFDAKIXHLFBN-UHFFFAOYSA-N 0.000 claims 1
- QRAJFZIVAGEPQU-UHFFFAOYSA-N 3-(4-methoxyphenyl)-8-[6-(methylamino)pyridin-3-yl]-1-pentan-2-yl-7H-purine-2,6-dione Chemical compound C(CC)C(C)N1C(=O)N(C=2N=C(NC=2C1=O)C=1C=NC(=CC=1)NC)C1=CC=C(C=C1)OC QRAJFZIVAGEPQU-UHFFFAOYSA-N 0.000 claims 1
- HXCINFYZZQPUQQ-UHFFFAOYSA-N 3-(4-methoxyphenyl)-8-[6-[(2-oxo-2-pyridin-3-ylethyl)amino]pyridin-3-yl]-1-pentan-2-yl-7H-purine-2,6-dione Chemical compound C(CC)C(C)N1C(=O)N(C=2N=C(NC=2C1=O)C=1C=NC(=CC=1)NCC(C1=CN=CC=C1)=O)C1=CC=C(C=C1)OC HXCINFYZZQPUQQ-UHFFFAOYSA-N 0.000 claims 1
- IWIRXFKTHJBLGG-UHFFFAOYSA-N 3-cyclopropyl-1-ethyl-8-[6-(2-methoxyethylamino)pyridin-3-yl]-7h-purine-2,6-dione Chemical compound C1=2N=C(C=3C=NC(NCCOC)=CC=3)NC=2C(=O)N(CC)C(=O)N1C1CC1 IWIRXFKTHJBLGG-UHFFFAOYSA-N 0.000 claims 1
- AXOZBTRTVSIHCK-UHFFFAOYSA-N 3-cyclopropyl-1-ethyl-8-[6-(methylamino)pyridin-3-yl]-7h-purine-2,6-dione Chemical compound C1=2N=C(C=3C=NC(NC)=CC=3)NC=2C(=O)N(CC)C(=O)N1C1CC1 AXOZBTRTVSIHCK-UHFFFAOYSA-N 0.000 claims 1
- FXYPFFWMBSZGOL-UHFFFAOYSA-N 3-cyclopropyl-8-[6-(methylamino)pyridin-3-yl]-1-propyl-7h-purine-2,6-dione Chemical compound C1=2N=C(C=3C=NC(NC)=CC=3)NC=2C(=O)N(CCC)C(=O)N1C1CC1 FXYPFFWMBSZGOL-UHFFFAOYSA-N 0.000 claims 1
- SPEBTNIPAFIDPC-UHFFFAOYSA-N 3-methyl-8-[6-(methylamino)pyridin-3-yl]-1-prop-2-ynyl-7h-purine-2,6-dione Chemical compound C1=NC(NC)=CC=C1C(N1)=NC2=C1C(=O)N(CC#C)C(=O)N2C SPEBTNIPAFIDPC-UHFFFAOYSA-N 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- GGFYNCWNVSRNQN-UHFFFAOYSA-N 7-(2-bromoethyl)-8-(6-chloropyridin-3-yl)-1,3-dipropylpurine-2,6-dione Chemical compound BrCCN1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C1=CC=C(Cl)N=C1 GGFYNCWNVSRNQN-UHFFFAOYSA-N 0.000 claims 1
- DVRPSYMPOGXTNQ-UHFFFAOYSA-N 8-(2,6-dichloropyridin-3-yl)-1,3-dipropyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C1=CC=C(Cl)N=C1Cl DVRPSYMPOGXTNQ-UHFFFAOYSA-N 0.000 claims 1
- YFZKDPFJCYQWAX-UHFFFAOYSA-N 8-(6-bromopyridin-3-yl)-1,3-diethyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CC)C(=O)N(CC)C=2N=C1C1=CC=C(Br)N=C1 YFZKDPFJCYQWAX-UHFFFAOYSA-N 0.000 claims 1
- HVSDJXOTPGRMDE-UHFFFAOYSA-N 8-(6-bromopyridin-3-yl)-1,3-dimethyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(C)C(=O)N(C)C=2N=C1C1=CC=C(Br)N=C1 HVSDJXOTPGRMDE-UHFFFAOYSA-N 0.000 claims 1
- RWCGREFAXNNUOP-UHFFFAOYSA-N 8-(6-bromopyridin-3-yl)-3-methyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)NC(=O)N(C)C=2N=C1C1=CC=C(Br)N=C1 RWCGREFAXNNUOP-UHFFFAOYSA-N 0.000 claims 1
- VXUBRKBECGMJLK-UHFFFAOYSA-N 8-(6-chloropyridin-3-yl)-1,3-diethyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CC)C(=O)N(CC)C=2N=C1C1=CC=C(Cl)N=C1 VXUBRKBECGMJLK-UHFFFAOYSA-N 0.000 claims 1
- ABZRXSOSKNAONT-UHFFFAOYSA-N 8-(6-chloropyridin-3-yl)-1-(3-fluoropropyl)-3,7-dihydropurine-2,6-dione Chemical compound FCCCN1C(=O)NC=2N=C(NC2C1=O)C=1C=NC(=CC1)Cl ABZRXSOSKNAONT-UHFFFAOYSA-N 0.000 claims 1
- SWVHDVTVWJZLCE-UHFFFAOYSA-N 8-(6-chloropyridin-3-yl)-1-propyl-3-prop-2-ynyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CC#C)C=2N=C1C1=CC=C(Cl)N=C1 SWVHDVTVWJZLCE-UHFFFAOYSA-N 0.000 claims 1
- AHRGRLCHURXYSA-UHFFFAOYSA-N 8-(6-chloropyridin-3-yl)-3-(4-methoxyphenyl)-1-pentan-2-yl-7H-purine-2,6-dione Chemical compound C(CC)C(C)N1C(=O)N(C=2N=C(NC=2C1=O)C=1C=NC(=CC=1)Cl)C1=CC=C(C=C1)OC AHRGRLCHURXYSA-UHFFFAOYSA-N 0.000 claims 1
- LTJPCVPDSNTQTL-UHFFFAOYSA-N 8-(6-chloropyridin-3-yl)-7-ethyl-1,3-dipropylpurine-2,6-dione Chemical compound CCN1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C1=CC=C(Cl)N=C1 LTJPCVPDSNTQTL-UHFFFAOYSA-N 0.000 claims 1
- LEIZTQAPCJCIGA-UHFFFAOYSA-N 8-(6-chloropyridin-3-yl)-7-methyl-1,3-dipropylpurine-2,6-dione Chemical compound CN1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C1=CC=C(Cl)N=C1 LEIZTQAPCJCIGA-UHFFFAOYSA-N 0.000 claims 1
- QPHLGOSAWIQSJO-UHFFFAOYSA-N 8-(6-piperidin-1-ylpyridin-3-yl)-1,3-dipropyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C(C=N1)=CC=C1N1CCCCC1 QPHLGOSAWIQSJO-UHFFFAOYSA-N 0.000 claims 1
- DHNDJKOEAQDJPD-UHFFFAOYSA-N 8-[2,6-bis(2-methoxyethyl)pyridin-3-yl]-1,3-dipropyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C1=CC=C(CCOC)N=C1CCOC DHNDJKOEAQDJPD-UHFFFAOYSA-N 0.000 claims 1
- CCCPTSIOCKSGTQ-UHFFFAOYSA-N 8-[2,6-bis(methylamino)pyridin-3-yl]-1,3-dipropyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C1=CC=C(NC)N=C1NC CCCPTSIOCKSGTQ-UHFFFAOYSA-N 0.000 claims 1
- JZXZWTFSLKREEI-UHFFFAOYSA-N 8-[2,6-bis[(2-oxo-2-pyridin-3-ylethyl)amino]pyridin-3-yl]-1,3-dipropyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C(C(=N1)NCC(=O)C=2C=NC=CC=2)=CC=C1NCC(=O)C1=CC=CN=C1 JZXZWTFSLKREEI-UHFFFAOYSA-N 0.000 claims 1
- YVMLHTYGOHBCGZ-UHFFFAOYSA-N 8-[2-chloro-6-(2-methoxyethylamino)pyridin-4-yl]-1,3-dipropyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C1=CC(Cl)=NC(NCCOC)=C1 YVMLHTYGOHBCGZ-UHFFFAOYSA-N 0.000 claims 1
- RDMGGJANVDQJIV-UHFFFAOYSA-N 8-[2-chloro-6-(methylamino)pyridin-4-yl]-1,3-dipropyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C1=CC(Cl)=NC(NC)=C1 RDMGGJANVDQJIV-UHFFFAOYSA-N 0.000 claims 1
- BHQUUGSUMICFPU-UHFFFAOYSA-N 8-[6-(1,4-diazepan-1-yl)pyridin-3-yl]-1,3-dipropyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C(C=N1)=CC=C1N1CCCNCC1 BHQUUGSUMICFPU-UHFFFAOYSA-N 0.000 claims 1
- YOIVNOQTNYHUPO-UHFFFAOYSA-N 8-[6-(2,2-diphenylethylamino)pyridin-3-yl]-1,3-dipropyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C(C=N1)=CC=C1NCC(C=1C=CC=CC=1)C1=CC=CC=C1 YOIVNOQTNYHUPO-UHFFFAOYSA-N 0.000 claims 1
- DFLYGAUEDKTJBE-UHFFFAOYSA-N 8-[6-(2-methoxyethyl)pyridin-3-yl]-3-methyl-7h-purine-2,6-dione Chemical compound C1=NC(CCOC)=CC=C1C(N1)=NC2=C1C(=O)NC(=O)N2C DFLYGAUEDKTJBE-UHFFFAOYSA-N 0.000 claims 1
- VTBPXOAZMUHOPB-UHFFFAOYSA-N 8-[6-(2-methoxyethylamino)pyridin-3-yl]-1,3-dipropyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C1=CC=C(NCCOC)N=C1 VTBPXOAZMUHOPB-UHFFFAOYSA-N 0.000 claims 1
- BXQBOSMOYFLWHN-UHFFFAOYSA-N 8-[6-(3-methylpiperidin-1-yl)pyridin-3-yl]-1,3-dipropyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C(C=N1)=CC=C1N1CCCC(C)C1 BXQBOSMOYFLWHN-UHFFFAOYSA-N 0.000 claims 1
- ZROHZMPUZNRGSI-UHFFFAOYSA-N 8-[6-(4-methylpiperazin-1-yl)pyridin-3-yl]-1,3-dipropyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C(C=N1)=CC=C1N1CCN(C)CC1 ZROHZMPUZNRGSI-UHFFFAOYSA-N 0.000 claims 1
- BIQZUYHQALHZQS-UHFFFAOYSA-N 8-[6-(benzylamino)pyridin-3-yl]-1,3-dipropyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C(C=N1)=CC=C1NCC1=CC=CC=C1 BIQZUYHQALHZQS-UHFFFAOYSA-N 0.000 claims 1
- ZMTZGWJTWLYECU-UHFFFAOYSA-N 8-[6-(cyclohexylamino)pyridin-3-yl]-1,3-dipropyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C(C=N1)=CC=C1NC1CCCCC1 ZMTZGWJTWLYECU-UHFFFAOYSA-N 0.000 claims 1
- OFMGPQKZHNIOPM-UHFFFAOYSA-N 8-[6-(cyclopentylamino)pyridin-3-yl]-1,3-dipropyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C(C=N1)=CC=C1NC1CCCC1 OFMGPQKZHNIOPM-UHFFFAOYSA-N 0.000 claims 1
- QZWYFQZRNPSEPZ-UHFFFAOYSA-N 8-[6-(cyclopropylamino)pyridin-3-yl]-1,3-diethyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CC)C(=O)N(CC)C=2N=C1C(C=N1)=CC=C1NC1CC1 QZWYFQZRNPSEPZ-UHFFFAOYSA-N 0.000 claims 1
- MFZLADREUMQWBO-UHFFFAOYSA-N 8-[6-(cyclopropylmethylamino)pyridin-3-yl]-1,3-diethyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CC)C(=O)N(CC)C=2N=C1C(C=N1)=CC=C1NCC1CC1 MFZLADREUMQWBO-UHFFFAOYSA-N 0.000 claims 1
- UKYSCFDLWQDFHM-UHFFFAOYSA-N 8-[6-(furan-2-ylmethylamino)pyridin-3-yl]-1,3-dipropyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C(C=N1)=CC=C1NCC1=CC=CO1 UKYSCFDLWQDFHM-UHFFFAOYSA-N 0.000 claims 1
- FQNDDLGLHZNNAJ-UHFFFAOYSA-N 8-[6-(pentan-3-ylamino)pyridin-3-yl]-1,3-dipropyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C1=CC=C(NC(CC)CC)N=C1 FQNDDLGLHZNNAJ-UHFFFAOYSA-N 0.000 claims 1
- RALCESMVPOPJOZ-UHFFFAOYSA-N 8-[6-[(2-hydroxy-2-phenylethyl)amino]pyridin-3-yl]-1,3-dipropyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C(C=N1)=CC=C1NCC(O)C1=CC=CC=C1 RALCESMVPOPJOZ-UHFFFAOYSA-N 0.000 claims 1
- FXQFULBXCYQFPU-UHFFFAOYSA-N 8-[6-[(2-methoxyphenyl)methylamino]pyridin-3-yl]-1,3-dipropyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C(C=N1)=CC=C1NCC1=CC=CC=C1OC FXQFULBXCYQFPU-UHFFFAOYSA-N 0.000 claims 1
- TUIJGAPHZLJUDI-UHFFFAOYSA-N 8-[6-[(2-methylphenyl)methylamino]pyridin-3-yl]-1,3-dipropyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C(C=N1)=CC=C1NCC1=CC=CC=C1C TUIJGAPHZLJUDI-UHFFFAOYSA-N 0.000 claims 1
- MVTNZBGCFDIGRY-UHFFFAOYSA-N 8-[6-[(2-oxo-2-pyridin-3-ylethyl)amino]pyridin-3-yl]-1,3-dipropyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C(C=N1)=CC=C1NCC(=O)C1=CC=CN=C1 MVTNZBGCFDIGRY-UHFFFAOYSA-N 0.000 claims 1
- HDYLXXLPNCGAKN-OLZOCXBDSA-N 8-[6-[(2s,5r)-2,5-dimethylpiperazin-1-yl]pyridin-3-yl]-1,3-diethyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CC)C(=O)N(CC)C=2N=C1C(C=N1)=CC=C1N1C[C@@H](C)NC[C@@H]1C HDYLXXLPNCGAKN-OLZOCXBDSA-N 0.000 claims 1
- AFCWVRSOHCYSRQ-UHFFFAOYSA-N 8-[6-[(3-methoxyphenyl)methylamino]pyridin-3-yl]-1,3-dipropyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C(C=N1)=CC=C1NCC1=CC=CC(OC)=C1 AFCWVRSOHCYSRQ-UHFFFAOYSA-N 0.000 claims 1
- XBOFEUPHLAXDSP-UHFFFAOYSA-N 8-[6-[(4-methoxyphenyl)methylamino]pyridin-3-yl]-1,3-dipropyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C(C=N1)=CC=C1NCC1=CC=C(OC)C=C1 XBOFEUPHLAXDSP-UHFFFAOYSA-N 0.000 claims 1
- ZNLBTZMIODYOAY-UHFFFAOYSA-N 8-[6-[2-(3,4-dimethoxyphenyl)ethylamino]pyridin-3-yl]-1,3-dipropyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C(C=N1)=CC=C1NCCC1=CC=C(OC)C(OC)=C1 ZNLBTZMIODYOAY-UHFFFAOYSA-N 0.000 claims 1
- QXNRKUQYMAGDHX-UHFFFAOYSA-N 8-[6-[2-(4-methoxyphenyl)ethylamino]pyridin-3-yl]-1,3-dipropyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C(C=N1)=CC=C1NCCC1=CC=C(OC)C=C1 QXNRKUQYMAGDHX-UHFFFAOYSA-N 0.000 claims 1
- BQRJONNWICMYSA-UHFFFAOYSA-N 8-[6-[[2-(6-chloropyridin-3-yl)-2-oxoethyl]amino]pyridin-3-yl]-1,3-diethyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CC)C(=O)N(CC)C=2N=C1C(C=N1)=CC=C1NCC(=O)C1=CC=C(Cl)N=C1 BQRJONNWICMYSA-UHFFFAOYSA-N 0.000 claims 1
- MGJXYCDMZLASBM-UHFFFAOYSA-N 8-[6-[[2-(6-chloropyridin-3-yl)-2-oxoethyl]amino]pyridin-3-yl]-3-(4-methoxyphenyl)-1-pentan-2-yl-7H-purine-2,6-dione Chemical compound C(CC)C(C)N1C(=O)N(C=2N=C(NC=2C1=O)C=1C=NC(=CC=1)NCC(C1=CN=C(C=C1)Cl)=O)C1=CC=C(C=C1)OC MGJXYCDMZLASBM-UHFFFAOYSA-N 0.000 claims 1
- YQIOUYLFRGXANI-UHFFFAOYSA-N 8-[6-[[2-oxo-2-[6-(trifluoromethyl)pyridin-3-yl]ethyl]amino]pyridin-3-yl]-1,3-dipropyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CCC)C=2N=C1C(C=N1)=CC=C1NCC(=O)C1=CC=C(C(F)(F)F)N=C1 YQIOUYLFRGXANI-UHFFFAOYSA-N 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 239000002126 C01EB10 - Adenosine Substances 0.000 claims 1
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 1
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 1
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 1
- 206010012735 Diarrhoea Diseases 0.000 claims 1
- 206010020751 Hypersensitivity Diseases 0.000 claims 1
- 206010022489 Insulin Resistance Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 206010063837 Reperfusion injury Diseases 0.000 claims 1
- 208000017442 Retinal disease Diseases 0.000 claims 1
- 206010038923 Retinopathy Diseases 0.000 claims 1
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims 1
- 229960005305 adenosine Drugs 0.000 claims 1
- 208000026935 allergic disease Diseases 0.000 claims 1
- 230000007815 allergy Effects 0.000 claims 1
- 230000008485 antagonism Effects 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000001207 fluorophenyl group Chemical group 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 208000028867 ischemia Diseases 0.000 claims 1
- 125000005956 isoquinolyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 125000005493 quinolyl group Chemical group 0.000 claims 1
- 208000024891 symptom Diseases 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
- IKWDLRGGUNRQAW-UHFFFAOYSA-N CC(C1)(C=C(CCC2)CC12O)NC Chemical compound CC(C1)(C=C(CCC2)CC12O)NC IKWDLRGGUNRQAW-UHFFFAOYSA-N 0.000 description 1
- FEWHVBXCYORMPQ-UHFFFAOYSA-N CC1CNC(CNC)C1 Chemical compound CC1CNC(CNC)C1 FEWHVBXCYORMPQ-UHFFFAOYSA-N 0.000 description 1
- HRLBSWFFGVIFIW-UHFFFAOYSA-N CN1C(C2)CNCC2C1 Chemical compound CN1C(C2)CNCC2C1 HRLBSWFFGVIFIW-UHFFFAOYSA-N 0.000 description 1
- GXIMUJOQZCMEFY-UHFFFAOYSA-N CN1C(CC2)CNC2C1 Chemical compound CN1C(CC2)CNC2C1 GXIMUJOQZCMEFY-UHFFFAOYSA-N 0.000 description 1
- YMTUWYHKZORWRX-UHFFFAOYSA-N CN1C(CC2)CNCC2C1 Chemical compound CN1C(CC2)CNCC2C1 YMTUWYHKZORWRX-UHFFFAOYSA-N 0.000 description 1
- RNIJSZGJNGTOTB-UHFFFAOYSA-N CNC1C(CC2)CC2C1 Chemical compound CNC1C(CC2)CC2C1 RNIJSZGJNGTOTB-UHFFFAOYSA-N 0.000 description 1
- UWBYHCLTULMDDX-UHFFFAOYSA-N CNC1C(CC2)CCN2C1 Chemical compound CNC1C(CC2)CCN2C1 UWBYHCLTULMDDX-UHFFFAOYSA-N 0.000 description 1
- LPNBBFKOUUSUDB-UHFFFAOYSA-N Cc(cc1)ccc1C(O)=O Chemical compound Cc(cc1)ccc1C(O)=O LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US49787503P | 2003-08-25 | 2003-08-25 | |
| US60/497,875 | 2003-08-25 | ||
| PCT/US2004/027133 WO2005021548A2 (en) | 2003-08-25 | 2004-08-20 | Substituted 8-heteroaryl xanthines |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007503443A JP2007503443A (ja) | 2007-02-22 |
| JP2007503443A5 true JP2007503443A5 (esLanguage) | 2007-06-14 |
| JP4769721B2 JP4769721B2 (ja) | 2011-09-07 |
Family
ID=34272616
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006524755A Expired - Lifetime JP4769721B2 (ja) | 2003-08-25 | 2004-08-20 | 置換８−ヘテロアリールキサンチン |
Country Status (19)
| Country | Link |
|---|---|
| US (3) | US7342006B2 (esLanguage) |
| EP (2) | EP2295434B1 (esLanguage) |
| JP (1) | JP4769721B2 (esLanguage) |
| KR (1) | KR101222364B1 (esLanguage) |
| CN (2) | CN101851238B (esLanguage) |
| AR (1) | AR045499A1 (esLanguage) |
| AU (1) | AU2004268964B2 (esLanguage) |
| BR (1) | BRPI0413922B8 (esLanguage) |
| CA (1) | CA2536553C (esLanguage) |
| DK (2) | DK1658291T3 (esLanguage) |
| ES (2) | ES2557310T3 (esLanguage) |
| IL (1) | IL173723A (esLanguage) |
| NZ (1) | NZ545715A (esLanguage) |
| PL (1) | PL1658291T3 (esLanguage) |
| PT (1) | PT1658291E (esLanguage) |
| RU (1) | RU2357969C2 (esLanguage) |
| TW (1) | TWI362390B (esLanguage) |
| WO (1) | WO2005021548A2 (esLanguage) |
| ZA (1) | ZA200602333B (esLanguage) |
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ556354A (en) * | 2001-10-01 | 2008-10-31 | Univ Virginia | 2-Propynyl adenosine analogs having A2A agonist activity and compositions thereof |
| US7317017B2 (en) * | 2002-11-08 | 2008-01-08 | Cv Therapeutics, Inc. | A2B adenosine receptor antagonists |
| BR0302965A (pt) * | 2002-02-01 | 2005-02-09 | King Pharmaceuticals Res & Dev | Composto e método de tratar doenças mediadas por receptores de adenosina a2b |
| CN101851238B (zh) * | 2003-08-25 | 2012-07-18 | 卓维斯医药品有限责任公司 | 取代的8-杂芳基黄嘌呤 |
| NZ585697A (en) * | 2004-08-02 | 2011-12-22 | Univ Virginia Patent Found | 2-propynyl adenosine analogs with modified 5'-ribose groups having A2A agonist activity |
| US7767677B2 (en) | 2004-09-20 | 2010-08-03 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-CoA desaturase inhibitors |
| AU2005286793A1 (en) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives for the treatment of diseases mediated by stearoyl-CoA desaturase enzymes |
| AU2005286728A1 (en) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as mediators of stearoyl-CoA desaturase |
| US8071603B2 (en) | 2004-09-20 | 2011-12-06 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-CoA desaturase inhibitors |
| EP1814551A2 (en) | 2004-09-20 | 2007-08-08 | Xenon Pharmaceuticals Inc. | Pyridazine derivatives for inhibiting human stearoyl-coa-desaturase |
| JP4958787B2 (ja) | 2004-09-20 | 2012-06-20 | ゼノン・ファーマシューティカルズ・インコーポレイテッド | ヒトステアロイル−ＣｏＡデサチュラーゼを阻害するためのピリジン誘導体 |
| CA2580762A1 (en) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as therapeutic agents |
| CA2580857A1 (en) | 2004-09-20 | 2006-09-28 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors |
| WO2006091897A2 (en) * | 2005-02-25 | 2006-08-31 | Adenosine Therapeutics, Llc | Derivatives of 8-substituted xanthines |
| US7598379B2 (en) | 2005-02-25 | 2009-10-06 | Pgx Health, Llc | Methods for the synthesis of unsymmetrical cycloalkyl substituted xanthines |
| US7618962B2 (en) * | 2005-02-25 | 2009-11-17 | Pgx Health, Llc | Pyrazolyl substituted xanthines |
| GB0510141D0 (en) * | 2005-05-18 | 2005-06-22 | Addex Pharmaceuticals Sa | Novel compounds B3 |
| MX2007015216A (es) | 2005-06-03 | 2008-02-22 | Xenon Pharmaceuticals Inc | Derivados de aminotiazol y sus usos como agentes terapeuticos. |
| CN101198608B (zh) * | 2005-06-16 | 2011-04-27 | 吉利德帕洛阿尔托股份有限公司 | A2b腺苷受体拮抗剂的前药 |
| ES2270715B1 (es) | 2005-07-29 | 2008-04-01 | Laboratorios Almirall S.A. | Nuevos derivados de pirazina. |
| WO2007020888A1 (ja) | 2005-08-12 | 2007-02-22 | Takeda Pharmaceutical Company Limited | 脳・神経細胞保護剤および睡眠障害治療薬 |
| US20070059740A1 (en) * | 2005-08-26 | 2007-03-15 | Linden Joel M | Method of targeting a2b adenosine receptor antagonist therapy |
| US7566401B2 (en) * | 2005-10-03 | 2009-07-28 | Kelm Mark A | Process for separating and isolating xanthines, individual polar protic monomers, and polar protic oligomers |
| ES2274712B1 (es) | 2005-10-06 | 2008-03-01 | Laboratorios Almirall S.A. | Nuevos derivados imidazopiridina. |
| US8178509B2 (en) * | 2006-02-10 | 2012-05-15 | University Of Virginia Patent Foundation | Method to treat sickle cell disease |
| GB0606774D0 (en) * | 2006-04-03 | 2006-05-10 | Novartis Ag | Organic compounds |
| US7884100B2 (en) * | 2006-06-16 | 2011-02-08 | Pgxhealth, Llc | Substituted 8-[6-amino-3-pyridyl]xanthines |
| UA105164C2 (en) | 2006-06-16 | 2014-04-25 | Догвуд Фармасьютикалз, Инк | Substituted 8-[6-amino-3-pyridyl]xanthines |
| US8188063B2 (en) * | 2006-06-19 | 2012-05-29 | University Of Virginia Patent Foundation | Use of adenosine A2A modulators to treat spinal cord injury |
| US8193200B2 (en) * | 2007-01-04 | 2012-06-05 | University Of Virginia Patent Foundation | Antagonists of A2B adenosine receptors for treatment of inflammatory bowel disease |
| RU2344137C1 (ru) * | 2007-07-18 | 2009-01-20 | Государственное образовательное учреждение высшего профессионального образования "БАШКИРСКИЙ ГОСУДАРСТВЕННЫЙ МЕДИЦИНСКИЙ УНИВЕРСИТЕТ Федерального Агентства по здравоохранению и социальному развитию" (ГОУ ВПО БГМУ РОСЗДРАВА) | Производные 8-амино-7-(2-гидроксипропил-1)-1,3-диметилксантина гидрохлорида, проявляющие гемореологическую активность |
| US7875608B2 (en) * | 2007-12-17 | 2011-01-25 | Thompson Robert D | Substituted 8-[6-amino-3pyridyl]xanthines |
| BRPI0909157A2 (pt) | 2008-03-26 | 2015-11-24 | Advinus Therapeutics Private Ltd | compostos heterocíclicos como antagonistas de receptores de adenosina |
| WO2010009194A1 (en) * | 2008-07-16 | 2010-01-21 | King Pharmaceuticals Research And Development, Inc. | Methods of treating atherosclerosis |
| AU2010222289B2 (en) | 2009-03-13 | 2013-07-11 | Advinus Therapeutics Private Limited | Substituted fused pyrimidine compounds |
| RU2404181C1 (ru) * | 2009-06-02 | 2010-11-20 | Государственное образовательное учреждение высшего профессионального образования "БАШКИРСКИЙ ГОСУДАРСТВЕННЫЙ МЕДИЦИНСКИЙ УНИВЕРСИТЕТ Федерального Агентства по здравоохранению и социальному развитию" (ГОУ ВПО БГМУ РОСЗДРАВА) | 3-метил-8-пиперазино-7-(тиетанил-3)-1-этилксантина гидрохлорид, проявляющий антиагрегационную и дезагрегационную активность |
| WO2011005871A1 (en) | 2009-07-07 | 2011-01-13 | Pgxhealth, Llc | Substituted 8-[6-carbonylamine-3-pyridyl]xanthines as adenosine a2b antagonists |
| JP5843778B2 (ja) | 2009-11-09 | 2016-01-13 | アドヴィナス・セラピューティックス・リミテッド | 置換縮合ピリミジン化合物、その調製およびその使用 |
| US8940751B2 (en) | 2010-09-13 | 2015-01-27 | Advinus Therapeutics Private Limited | Purine compounds as prodrugs of A2B adenosine receptor antagonists, their process and medicinal applications |
| EP2465859A1 (en) * | 2010-12-08 | 2012-06-20 | Life & Brain GmbH | 8-Triazolylxanthine derivatives, processes for their production and their use as adenosine receptor antagonists |
| CN102532137B (zh) * | 2011-12-05 | 2014-12-10 | 辽宁医学院 | 8-吡唑取代黄嘌呤类a2b腺苷受体拮抗剂及其合成方法和应用 |
| US11370792B2 (en) | 2015-12-14 | 2022-06-28 | Raze Therapeutics, Inc. | Caffeine inhibitors of MTHFD2 and uses thereof |
| US11548867B2 (en) | 2017-07-19 | 2023-01-10 | Idea Ya Biosciences, Inc. | Amido compounds as AhR modulators |
| WO2021194623A1 (en) * | 2020-03-26 | 2021-09-30 | Inspyr Therapeutics, Inc. | 8-substituted diaryl xanthines as dual a 2a-a 2b antagonists |
| AU2022275564A1 (en) * | 2021-05-18 | 2023-12-07 | Adovate, Llc | Cyclic amide-containing pyridyl xanthines as a 2b antagonists |
| CN113262882B (zh) * | 2021-07-21 | 2021-09-17 | 北京矿冶研究总院 | 阳离子捕收剂、制备方法及在磷矿反浮选中的应用 |
| WO2024050825A1 (en) * | 2022-09-09 | 2024-03-14 | National Institute Of Biological Sciences, Beijing | Compounds as mlkl inhibitors |
Family Cites Families (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4559157A (en) | 1983-04-21 | 1985-12-17 | Creative Products Resource Associates, Ltd. | Cosmetic applicator useful for skin moisturizing |
| LU84979A1 (fr) | 1983-08-30 | 1985-04-24 | Oreal | Composition cosmetique ou pharmaceutique sous forme aqueuse ou anhydre dont la phase grasse contient un polyether oligomere et polyethers oligomeres nouveaux |
| US4820508A (en) | 1987-06-23 | 1989-04-11 | Neutrogena Corporation | Skin protective composition |
| US4992478A (en) | 1988-04-04 | 1991-02-12 | Warner-Lambert Company | Antiinflammatory skin moisturizing composition and method of preparing same |
| US4938949A (en) | 1988-09-12 | 1990-07-03 | University Of New York | Treatment of damaged bone marrow and dosage units therefor |
| DE3843117A1 (de) * | 1988-12-22 | 1990-06-28 | Boehringer Ingelheim Kg | Neue xanthinderivate mit adenosin-antagonistischer wirkung |
| JPH06102662B2 (ja) * | 1989-09-01 | 1994-12-14 | 協和醗酵工業株式会社 | キサンチン誘導体 |
| AU1507099A (en) * | 1997-12-15 | 1999-07-05 | Kyowa Hakko Kogyo Co. Ltd. | Preventives/remedies for sleep disturbance |
| US6117878A (en) * | 1998-02-24 | 2000-09-12 | University Of Virginia | 8-phenyl- or 8-cycloalkyl xanthine antagonists of A2B human adenosine receptors |
| US6060481A (en) | 1998-05-28 | 2000-05-09 | The Penn State Research Foundation | Method for improving insulin sensitivity using an adenosine receptor antagonist |
| GB9817623D0 (en) * | 1998-08-13 | 1998-10-07 | Glaxo Group Ltd | Pharmaceutical compounds |
| US6545002B1 (en) | 1999-06-01 | 2003-04-08 | University Of Virginia Patent Foundation | Substituted 8-phenylxanthines useful as antagonists of A2B adenosine receptors |
| DE60026559T2 (de) * | 1999-10-29 | 2006-12-14 | Kyowa Hakko Kogyo Co., Ltd. | Arzneimittel gegen essstörungen |
| WO2001060350A2 (en) * | 2000-02-17 | 2001-08-23 | Cv Therapeutics, Inc. | Method for identifying and using a2b adenosine receptor antagonists to mediate mammalian cell proliferation |
| US7304070B2 (en) | 2001-11-09 | 2007-12-04 | Cv Therapeutics, Inc. | A2B adenosine receptor antagonists |
| US7317017B2 (en) * | 2002-11-08 | 2008-01-08 | Cv Therapeutics, Inc. | A2B adenosine receptor antagonists |
| JP4350517B2 (ja) | 2001-11-09 | 2009-10-21 | シーブイ・セラピューティクス・インコーポレイテッド | Ａ２ｂアデノシン受容体アンタゴニスト |
| US6977300B2 (en) | 2001-11-09 | 2005-12-20 | Cv Therapeutics, Inc. | A2B adenosine receptor antagonists |
| BR0302965A (pt) * | 2002-02-01 | 2005-02-09 | King Pharmaceuticals Res & Dev | Composto e método de tratar doenças mediadas por receptores de adenosina a2b |
| US7034070B2 (en) * | 2002-09-27 | 2006-04-25 | Vincent Chuang | Arylalkyl aminofunctional silanes for epoxy laminates |
| US7148229B2 (en) | 2003-02-19 | 2006-12-12 | Hoffman-La Roche Inc. | Sulfonamide substituted xanthine derivatives |
| CN101851238B (zh) | 2003-08-25 | 2012-07-18 | 卓维斯医药品有限责任公司 | 取代的8-杂芳基黄嘌呤 |
| RU2385322C2 (ru) | 2004-09-01 | 2010-03-27 | Си Ви Терапьютикс, Инк. | Способ заживления ран с применением антагонистов аденозинового рецептора a2b |
| JP2008516969A (ja) | 2004-10-15 | 2008-05-22 | シーブイ・セラピューティクス・インコーポレイテッド | Ａ２ｂアデノシン受容体アンタゴニストを使用した、気道のリモデリングおよび肺の炎症の予防および処置の方法 |
| US7601723B2 (en) | 2005-02-25 | 2009-10-13 | Pgx Health, Llc | Pyridyl substituted xanthines |
| WO2006091897A2 (en) | 2005-02-25 | 2006-08-31 | Adenosine Therapeutics, Llc | Derivatives of 8-substituted xanthines |
| US7598379B2 (en) | 2005-02-25 | 2009-10-06 | Pgx Health, Llc | Methods for the synthesis of unsymmetrical cycloalkyl substituted xanthines |
| US7618962B2 (en) | 2005-02-25 | 2009-11-17 | Pgx Health, Llc | Pyrazolyl substituted xanthines |
| CN101198608B (zh) | 2005-06-16 | 2011-04-27 | 吉利德帕洛阿尔托股份有限公司 | A2b腺苷受体拮抗剂的前药 |
| CA2646333C (en) * | 2006-03-17 | 2014-06-17 | Cv Therapeutics, Inc. | Method of preventing and treating hepatic disease using a2b adenosine receptor antagonists |
| US7884100B2 (en) | 2006-06-16 | 2011-02-08 | Pgxhealth, Llc | Substituted 8-[6-amino-3-pyridyl]xanthines |
| US7767685B2 (en) | 2006-06-29 | 2010-08-03 | King Pharmaceuticals Research And Development, Inc. | Adenosine A2B receptor antagonists |
| US7875608B2 (en) * | 2007-12-17 | 2011-01-25 | Thompson Robert D | Substituted 8-[6-amino-3pyridyl]xanthines |
| BRPI0909157A2 (pt) * | 2008-03-26 | 2015-11-24 | Advinus Therapeutics Private Ltd | compostos heterocíclicos como antagonistas de receptores de adenosina |
-
2004
- 2004-08-20 CN CN2010101556967A patent/CN101851238B/zh not_active Expired - Fee Related
- 2004-08-20 US US10/923,592 patent/US7342006B2/en not_active Expired - Lifetime
- 2004-08-20 CN CN2004800314554A patent/CN1894250B/zh not_active Expired - Fee Related
- 2004-08-20 NZ NZ545715A patent/NZ545715A/en not_active IP Right Cessation
- 2004-08-20 AU AU2004268964A patent/AU2004268964B2/en not_active Ceased
- 2004-08-20 JP JP2006524755A patent/JP4769721B2/ja not_active Expired - Lifetime
- 2004-08-20 WO PCT/US2004/027133 patent/WO2005021548A2/en not_active Ceased
- 2004-08-20 RU RU2006109474/04A patent/RU2357969C2/ru active
- 2004-08-20 ES ES10012271.2T patent/ES2557310T3/es not_active Expired - Lifetime
- 2004-08-20 EP EP10012271.2A patent/EP2295434B1/en not_active Expired - Lifetime
- 2004-08-20 DK DK04781752.3T patent/DK1658291T3/da active
- 2004-08-20 DK DK10012271.2T patent/DK2295434T3/en active
- 2004-08-20 CA CA2536553A patent/CA2536553C/en not_active Expired - Lifetime
- 2004-08-20 PT PT47817523T patent/PT1658291E/pt unknown
- 2004-08-20 BR BRPI0413922A patent/BRPI0413922B8/pt not_active IP Right Cessation
- 2004-08-20 EP EP04781752.3A patent/EP1658291B1/en not_active Expired - Lifetime
- 2004-08-20 ES ES04781752.3T patent/ES2440467T3/es not_active Expired - Lifetime
- 2004-08-20 KR KR1020067003776A patent/KR101222364B1/ko not_active Expired - Fee Related
- 2004-08-20 PL PL04781752T patent/PL1658291T3/pl unknown
- 2004-08-25 AR ARP040103058A patent/AR045499A1/es not_active Application Discontinuation
- 2004-08-26 TW TW093125436A patent/TWI362390B/zh not_active IP Right Cessation
-
2006
- 2006-02-14 IL IL173723A patent/IL173723A/en active IP Right Grant
- 2006-03-22 ZA ZA200602333A patent/ZA200602333B/en unknown
-
2007
- 2007-12-14 US US11/956,876 patent/US7732455B2/en not_active Expired - Lifetime
-
2010
- 2010-04-19 US US12/762,711 patent/US20100273780A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2007503443A5 (esLanguage) | ||
| RU2006109474A (ru) | Замещенные 8-гетероарилксантины | |
| JP7181967B2 (ja) | 一過性受容体電位ａ１イオンチャネルの阻害 | |
| AU761694B2 (en) | QT dispersion and heart rate variability improvement with CRF antagonists to prevent sudden death | |
| EP3877376B1 (en) | Pyridazinone compounds and uses thereof | |
| CA2189830C (en) | Uses for corticotropin releasing factor atagonists | |
| HRP20251479T1 (hr) | Pesticidno aktivni kondenzirani biciklički heteroaromatski spojevi | |
| CA2290766C (en) | Method of treating nitrate-induced tolerance | |
| RU2018138050A (ru) | Производные тиазолопиридина как агонисты gpr119 | |
| JP2019535664A5 (esLanguage) | ||
| CA2515197A1 (en) | Pyrazolopyridine derivates | |
| CA2644841C (en) | Use of c-src inhibitors in combination with a pyrimidylaminobenzamide compound for the treatment of leukemia | |
| CA2643177A1 (en) | Multi-cyclic compounds for treating cancer | |
| JP2004515550A5 (esLanguage) | ||
| KR20060110006A (ko) | 비전형 항정신병제와 코르티코트로핀 방출 인자 길항제의치료적 조합물 | |
| HRP20192151T1 (hr) | Derivati izokromena kao inhibitori fosfoinozitid 3-kinaza | |
| JP2016537384A5 (esLanguage) | ||
| JP2019530708A5 (esLanguage) | ||
| JP2007500130A5 (esLanguage) | ||
| HK40091925A (en) | Pyridazinone compounds and uses thereof | |
| RU2021138377A (ru) | Производные пиридопиримидинов в качестве ингибиторов p2x3 | |
| HK40057226B (en) | Pyridazinone compounds and uses thereof | |
| HK40057226A (en) | Pyridazinone compounds and uses thereof | |
| JPWO2002019975A1 (ja) | 育毛剤 |