JP2007503443A5 - - Google Patents
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- 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
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- 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
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Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1434782A2 (en) * | 2001-10-01 | 2004-07-07 | University of Virginia Patent Foundation | 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 |
| MXPA03008967A (es) * | 2002-02-01 | 2004-02-12 | King Pharmaceuticals Res & Dev | Antagonistas receptores de 8-heteroarilo xantina adenosina a-2b. |
| ES2557310T3 (es) * | 2003-08-25 | 2016-01-25 | Dogwood Pharmaceuticals, Inc. | 8-heteroaril xantinas substituidas |
| AU2005267706B2 (en) * | 2004-08-02 | 2011-12-08 | University Of Virginia Patent Foundation | 2-propynyl adenosine analogs with modified 5'-ribose groups having A2A agonist activity |
| EP1807085B1 (en) * | 2004-09-20 | 2013-08-21 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors |
| EP2289510A1 (en) | 2004-09-20 | 2011-03-02 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives for the treatment of diseases mediated by stearoyl-coa desaturase enzymes |
| AR051091A1 (es) | 2004-09-20 | 2006-12-20 | Xenon Pharmaceuticals Inc | Derivados heterociclicos y su uso como inhibidores de la estearoil-coa desaturasa |
| EP1827438B2 (en) | 2004-09-20 | 2014-12-10 | Xenon Pharmaceuticals Inc. | Piperazin derivatives for inhibiting human stearoyl-coa-desaturase |
| US7829712B2 (en) | 2004-09-20 | 2010-11-09 | Xenon Pharmaceuticals Inc. | Pyridazine derivatives for inhibiting human stearoyl-CoA-desaturase |
| 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 |
| AU2005286648A1 (en) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-CoA desaturase inhibitors |
| US7579348B2 (en) * | 2005-02-25 | 2009-08-25 | Pgxhealth, Llc | Derivatives of 8-substituted xanthines |
| WO2006091898A2 (en) * | 2005-02-25 | 2006-08-31 | Adenosine Therapeutics, Llc | Pyrazolyl substituted xanthines |
| US7598379B2 (en) | 2005-02-25 | 2009-10-06 | Pgx Health, Llc | Methods for the synthesis of unsymmetrical cycloalkyl substituted xanthines |
| GB0510141D0 (en) * | 2005-05-18 | 2005-06-22 | Addex Pharmaceuticals Sa | Novel compounds B3 |
| AU2006343359A1 (en) | 2005-06-03 | 2007-11-15 | Xenon Pharmaceuticals Inc. | Aminothiazole derivatives as human stearoyl-coa desaturase inhibitors |
| EP1891070A1 (en) * | 2005-06-16 | 2008-02-27 | Cv Therapeutics, Inc. | Prodrugs of a2b adenosine receptor antagonists |
| 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. |
| WO2007120972A2 (en) * | 2006-02-10 | 2007-10-25 | 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 |
| EP2268641B1 (en) | 2008-03-26 | 2014-09-03 | Advinus Therapeutics Pvt. Ltd. | Heterocyclic compounds as adenosine receptor antagonist |
| JP2011528364A (ja) * | 2008-07-16 | 2011-11-17 | キング・ファーマシューティカルズ・リサーチ・アンド・デベロプメント・インコーポレイティッド | アテローム性動脈硬化症の治療 |
| JP5765239B2 (ja) | 2009-03-13 | 2015-08-19 | 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 |
| 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 |
| CN103261200B (zh) | 2010-09-13 | 2016-03-30 | 阿迪维纳斯疗法有限公司 | 作为a2b腺苷受体拮抗剂的前药的嘌呤化合物、它们的制备方法及医药用途 |
| 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 |
| WO2019018562A1 (en) | 2017-07-19 | 2019-01-24 | Ideaya Biosciences, Inc. | AMIDO COMPOUND AS MODULATORS OF AHR |
| EP4126866A1 (en) * | 2020-03-26 | 2023-02-08 | Inspyr Therapeutics, Inc. | 8-substituted diaryl xanthines as dual a2a-a2b 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 |
| DE8817122U1 (de) * | 1988-12-22 | 1993-02-04 | Boehringer Ingelheim Kg, 55218 Ingelheim | Neue Xanthinderivate mit Adenosinantogenistischer 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 |
| EP1234576B1 (en) * | 1999-10-29 | 2006-03-08 | Kyowa Hakko Kogyo Co., Ltd. | Pharmaceutical composition for eating disorders |
| CA2400206A1 (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 |
| US6977300B2 (en) * | 2001-11-09 | 2005-12-20 | Cv Therapeutics, Inc. | A2B adenosine receptor antagonists |
| DK1444233T3 (da) * | 2001-11-09 | 2011-10-17 | Gilead Palo Alto Inc | A2B-adenosinreceptorantagonister |
| US7317017B2 (en) * | 2002-11-08 | 2008-01-08 | Cv Therapeutics, Inc. | A2B adenosine receptor antagonists |
| MXPA03008967A (es) * | 2002-02-01 | 2004-02-12 | King Pharmaceuticals Res & Dev | Antagonistas receptores de 8-heteroarilo xantina adenosina a-2b. |
| 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 |
| ES2557310T3 (es) * | 2003-08-25 | 2016-01-25 | Dogwood Pharmaceuticals, Inc. | 8-heteroaril xantinas substituidas |
| MX2007002437A (es) * | 2004-09-01 | 2007-08-14 | Cv Therapeutics Inc | Metodo para el sanado de heridas utilizando antagonistas del receptor de adenosina a2b. |
| EP1799221A1 (en) * | 2004-10-15 | 2007-06-27 | Cv Therapeutics, Inc. | Method of preventing and treating airway remodeling and pulmonary inflammation using a2b adenosine receptor antagonists |
| US7579348B2 (en) * | 2005-02-25 | 2009-08-25 | Pgxhealth, Llc | Derivatives of 8-substituted xanthines |
| US7601723B2 (en) * | 2005-02-25 | 2009-10-13 | Pgx Health, Llc | Pyridyl substituted xanthines |
| WO2006091898A2 (en) * | 2005-02-25 | 2006-08-31 | Adenosine Therapeutics, Llc | Pyrazolyl substituted xanthines |
| US7598379B2 (en) * | 2005-02-25 | 2009-10-06 | Pgx Health, Llc | Methods for the synthesis of unsymmetrical cycloalkyl substituted xanthines |
| EP1891070A1 (en) * | 2005-06-16 | 2008-02-27 | Cv Therapeutics, Inc. | Prodrugs of a2b adenosine receptor antagonists |
| AU2007227021B2 (en) * | 2006-03-17 | 2012-12-20 | Gilead Sciences, 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 |
| EP2268641B1 (en) * | 2008-03-26 | 2014-09-03 | Advinus Therapeutics Pvt. Ltd. | Heterocyclic compounds as adenosine receptor antagonist |
-
2004
- 2004-08-20 ES ES10012271.2T patent/ES2557310T3/es not_active Expired - Lifetime
- 2004-08-20 PT PT47817523T patent/PT1658291E/pt unknown
- 2004-08-20 RU RU2006109474/04A patent/RU2357969C2/ru active
- 2004-08-20 WO PCT/US2004/027133 patent/WO2005021548A2/en not_active Ceased
- 2004-08-20 JP JP2006524755A patent/JP4769721B2/ja not_active Expired - Lifetime
- 2004-08-20 US US10/923,592 patent/US7342006B2/en not_active Expired - Lifetime
- 2004-08-20 EP EP04781752.3A patent/EP1658291B1/en not_active Expired - Lifetime
- 2004-08-20 AU AU2004268964A patent/AU2004268964B2/en not_active Ceased
- 2004-08-20 CA CA2536553A patent/CA2536553C/en not_active Expired - Lifetime
- 2004-08-20 PL PL04781752T patent/PL1658291T3/pl unknown
- 2004-08-20 BR BRPI0413922A patent/BRPI0413922B8/pt not_active IP Right Cessation
- 2004-08-20 CN CN2010101556967A patent/CN101851238B/zh not_active Expired - Fee Related
- 2004-08-20 ES ES04781752.3T patent/ES2440467T3/es not_active Expired - Lifetime
- 2004-08-20 NZ NZ545715A patent/NZ545715A/en not_active IP Right Cessation
- 2004-08-20 DK DK10012271.2T patent/DK2295434T3/en active
- 2004-08-20 KR KR1020067003776A patent/KR101222364B1/ko not_active Expired - Fee Related
- 2004-08-20 EP EP10012271.2A patent/EP2295434B1/en not_active Expired - Lifetime
- 2004-08-20 CN CN2004800314554A patent/CN1894250B/zh not_active Expired - Fee Related
- 2004-08-20 DK DK04781752.3T patent/DK1658291T3/da active
- 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
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2010
- 2010-04-19 US US12/762,711 patent/US20100273780A1/en not_active Abandoned
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