ES2257103T3 - 4-amino-2-aril-ciclopenta(d)pirimidinas sustituidas, su preparacion, su uso y preparados farmaceuticos que las contienen. - Google Patents
4-amino-2-aril-ciclopenta(d)pirimidinas sustituidas, su preparacion, su uso y preparados farmaceuticos que las contienen.Info
- Publication number
- ES2257103T3 ES2257103T3 ES99972626T ES99972626T ES2257103T3 ES 2257103 T3 ES2257103 T3 ES 2257103T3 ES 99972626 T ES99972626 T ES 99972626T ES 99972626 T ES99972626 T ES 99972626T ES 2257103 T3 ES2257103 T3 ES 2257103T3
- Authority
- ES
- Spain
- Prior art keywords
- phenyl
- alkyl
- cyclopenta
- dihydro
- pyrimidine
- 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.)
- Expired - Lifetime
Links
- 238000002360 preparation method Methods 0.000 title claims description 14
- 239000000825 pharmaceutical preparation Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 84
- -1 hydroxy, amino Chemical group 0.000 claims abstract description 73
- 125000001424 substituent group Chemical group 0.000 claims abstract description 65
- 150000003839 salts Chemical class 0.000 claims abstract description 48
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 37
- 239000000203 mixture Substances 0.000 claims abstract description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 30
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 25
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
- 239000001257 hydrogen Substances 0.000 claims abstract description 18
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 16
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 16
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 7
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 239000003814 drug Substances 0.000 claims description 13
- 238000002560 therapeutic procedure Methods 0.000 claims description 11
- 201000010099 disease Diseases 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 238000011321 prophylaxis Methods 0.000 claims description 10
- RQFCJASXJCIDSX-UUOKFMHZSA-N guanosine 5'-monophosphate Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O RQFCJASXJCIDSX-UUOKFMHZSA-N 0.000 claims description 9
- 101710095468 Cyclase Proteins 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 5
- 206010002383 Angina Pectoris Diseases 0.000 claims description 4
- 201000001320 Atherosclerosis Diseases 0.000 claims description 4
- 241000790917 Dioxys <bee> Species 0.000 claims description 4
- 206010020772 Hypertension Diseases 0.000 claims description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 208000007536 Thrombosis Diseases 0.000 claims description 4
- 210000004369 blood Anatomy 0.000 claims description 4
- 239000008280 blood Substances 0.000 claims description 4
- 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 description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- YFFIDZJIZDLWDB-WKILWMFISA-N C1=CC(C)=CC=C1C(N=C1N[C@@H]2CC[C@@H](O)CC2)=NC2=C1CCC2 Chemical compound C1=CC(C)=CC=C1C(N=C1N[C@@H]2CC[C@@H](O)CC2)=NC2=C1CCC2 YFFIDZJIZDLWDB-WKILWMFISA-N 0.000 claims description 3
- YCGULRPNRQSLEY-SHTZXODSSA-N C1C[C@@H](O)CC[C@@H]1NC1=NC(C=2C=C(Cl)C=C(Cl)C=2)=NC2=C1CCC2 Chemical compound C1C[C@@H](O)CC[C@@H]1NC1=NC(C=2C=C(Cl)C=C(Cl)C=2)=NC2=C1CCC2 YCGULRPNRQSLEY-SHTZXODSSA-N 0.000 claims description 3
- UYSQYXCWLRFPRE-SHTZXODSSA-N C1C[C@@H](O)CC[C@@H]1NC1=NC(C=2C=CC(Cl)=CC=2)=NC2=C1CCC2 Chemical compound C1C[C@@H](O)CC[C@@H]1NC1=NC(C=2C=CC(Cl)=CC=2)=NC2=C1CCC2 UYSQYXCWLRFPRE-SHTZXODSSA-N 0.000 claims description 3
- 208000010228 Erectile Dysfunction Diseases 0.000 claims description 3
- 206010019280 Heart failures Diseases 0.000 claims description 3
- 150000001204 N-oxides Chemical class 0.000 claims description 3
- 208000006011 Stroke Diseases 0.000 claims description 3
- 230000002425 cardiocirculatory effect Effects 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 claims description 3
- 201000001881 impotence Diseases 0.000 claims description 3
- 208000010125 myocardial infarction Diseases 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- MDLRUXNZLBAKEZ-UHFFFAOYSA-N 2-(3,5-dichlorophenyl)-n-(pyridin-3-ylmethyl)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-amine Chemical compound ClC1=CC(Cl)=CC(C=2N=C(NCC=3C=NC=CC=3)C=3CCCC=3N=2)=C1 MDLRUXNZLBAKEZ-UHFFFAOYSA-N 0.000 claims description 2
- KNMVHYWDSWWOKN-UHFFFAOYSA-N 2-(3-chlorophenyl)-n-(pyridin-3-ylmethyl)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-amine Chemical compound ClC1=CC=CC(C=2N=C(NCC=3C=NC=CC=3)C=3CCCC=3N=2)=C1 KNMVHYWDSWWOKN-UHFFFAOYSA-N 0.000 claims description 2
- WZWVYYXJHMVYNN-UHFFFAOYSA-N 2-(4-chlorophenyl)-n-(2-methylpropyl)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-amine Chemical compound N=1C=2CCCC=2C(NCC(C)C)=NC=1C1=CC=C(Cl)C=C1 WZWVYYXJHMVYNN-UHFFFAOYSA-N 0.000 claims description 2
- XXBCZFGWMYQUMC-UHFFFAOYSA-N 2-(4-chlorophenyl)-n-(pyridin-3-ylmethyl)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-amine Chemical compound C1=CC(Cl)=CC=C1C(N=C1NCC=2C=NC=CC=2)=NC2=C1CCC2 XXBCZFGWMYQUMC-UHFFFAOYSA-N 0.000 claims description 2
- NDHSLSZOESUPPN-UHFFFAOYSA-N 2-(4-chlorophenyl)-n-cyclopentyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-amine Chemical compound C1=CC(Cl)=CC=C1C(N=C1NC2CCCC2)=NC2=C1CCC2 NDHSLSZOESUPPN-UHFFFAOYSA-N 0.000 claims description 2
- CGYLYGPMMOXDKO-UHFFFAOYSA-N 2-(4-methylphenyl)-n-(pyridin-3-ylmethyl)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-amine Chemical compound C1=CC(C)=CC=C1C(N=C1NCC=2C=NC=CC=2)=NC2=C1CCC2 CGYLYGPMMOXDKO-UHFFFAOYSA-N 0.000 claims description 2
- QZZZIWCTHRRLHS-UHFFFAOYSA-N 2-[[2-(3-chlorophenyl)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]amino]ethanol Chemical compound N=1C=2CCCC=2C(NCCO)=NC=1C1=CC=CC(Cl)=C1 QZZZIWCTHRRLHS-UHFFFAOYSA-N 0.000 claims description 2
- SAQGBDRYBGEFIG-UHFFFAOYSA-N 2-[[2-(4-chlorophenyl)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]amino]ethanol Chemical compound N=1C=2CCCC=2C(NCCO)=NC=1C1=CC=C(Cl)C=C1 SAQGBDRYBGEFIG-UHFFFAOYSA-N 0.000 claims description 2
- ASALTPIJADNPFQ-UHFFFAOYSA-N 3-[[2-(4-methoxyphenyl)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]amino]propan-1-ol Chemical compound C1=CC(OC)=CC=C1C(N=C1NCCCO)=NC2=C1CCC2 ASALTPIJADNPFQ-UHFFFAOYSA-N 0.000 claims description 2
- LAXAXXLEFJERMU-UHFFFAOYSA-N 4-[4-(3-methoxypropylamino)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-2-yl]benzonitrile Chemical compound N=1C=2CCCC=2C(NCCCOC)=NC=1C1=CC=C(C#N)C=C1 LAXAXXLEFJERMU-UHFFFAOYSA-N 0.000 claims description 2
- JUTHAFDLHUNZBH-UHFFFAOYSA-N 4-[4-(benzylamino)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-2-yl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1C(N=C1NCC=2C=CC=CC=2)=NC2=C1CCC2 JUTHAFDLHUNZBH-UHFFFAOYSA-N 0.000 claims description 2
- JSNYFSFWTAUTFR-UHFFFAOYSA-N 4-[4-(pyridin-3-ylmethylamino)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-2-yl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1C(N=C1NCC=2C=NC=CC=2)=NC2=C1CCC2 JSNYFSFWTAUTFR-UHFFFAOYSA-N 0.000 claims description 2
- ISSVEEMYWVLUBE-UHFFFAOYSA-N 4-[[2-(3,5-dichlorophenyl)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]amino]butan-1-ol Chemical compound N=1C=2CCCC=2C(NCCCCO)=NC=1C1=CC(Cl)=CC(Cl)=C1 ISSVEEMYWVLUBE-UHFFFAOYSA-N 0.000 claims description 2
- 206010052337 Diastolic dysfunction Diseases 0.000 claims description 2
- 206010048554 Endothelial dysfunction Diseases 0.000 claims description 2
- 208000011514 Familial renal glucosuria Diseases 0.000 claims description 2
- 206010020852 Hypertonia Diseases 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 208000006673 asthma Diseases 0.000 claims description 2
- 208000020832 chronic kidney disease Diseases 0.000 claims description 2
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 2
- 230000008694 endothelial dysfunction Effects 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- MEVSBTPHUHIQMQ-UHFFFAOYSA-N n-[2-(2-chlorophenyl)ethyl]-2-(4-methoxyphenyl)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1C(N=C1NCCC=2C(=CC=CC=2)Cl)=NC2=C1CCC2 MEVSBTPHUHIQMQ-UHFFFAOYSA-N 0.000 claims description 2
- HXKXDHGVMNKZKN-UHFFFAOYSA-N n-butyl-2-(3,4-dimethoxyphenyl)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-amine Chemical compound N=1C=2CCCC=2C(NCCCC)=NC=1C1=CC=C(OC)C(OC)=C1 HXKXDHGVMNKZKN-UHFFFAOYSA-N 0.000 claims description 2
- BMQFHIMGDYQPLP-UHFFFAOYSA-N n-butyl-2-(3,5-dichlorophenyl)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-amine Chemical compound N=1C=2CCCC=2C(NCCCC)=NC=1C1=CC(Cl)=CC(Cl)=C1 BMQFHIMGDYQPLP-UHFFFAOYSA-N 0.000 claims description 2
- PMPOELUYAFWYBN-UHFFFAOYSA-N n-butyl-2-(3-chlorophenyl)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-amine Chemical compound N=1C=2CCCC=2C(NCCCC)=NC=1C1=CC=CC(Cl)=C1 PMPOELUYAFWYBN-UHFFFAOYSA-N 0.000 claims description 2
- XBTOUXZSDWFOJV-UHFFFAOYSA-N n-butyl-2-(4-methoxyphenyl)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-amine Chemical compound N=1C=2CCCC=2C(NCCCC)=NC=1C1=CC=C(OC)C=C1 XBTOUXZSDWFOJV-UHFFFAOYSA-N 0.000 claims description 2
- YLOXCZMZUXEPAK-UHFFFAOYSA-N n-butyl-2-(4-methylphenyl)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-amine Chemical compound N=1C=2CCCC=2C(NCCCC)=NC=1C1=CC=C(C)C=C1 YLOXCZMZUXEPAK-UHFFFAOYSA-N 0.000 claims description 2
- XKNJKKXCPOGINE-UHFFFAOYSA-N n-cyclohexyl-2-(3,4-dimethoxyphenyl)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-amine Chemical compound C1=C(OC)C(OC)=CC=C1C(N=C1NC2CCCCC2)=NC2=C1CCC2 XKNJKKXCPOGINE-UHFFFAOYSA-N 0.000 claims description 2
- AZVDCNKFNRCARM-UHFFFAOYSA-N n-cyclohexyl-2-(4-methoxyphenyl)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1C(N=C1NC2CCCCC2)=NC2=C1CCC2 AZVDCNKFNRCARM-UHFFFAOYSA-N 0.000 claims description 2
- PPRZHPKKDVNLTJ-UHFFFAOYSA-N n-cyclohexyl-2-(4-methylphenyl)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-amine Chemical compound C1=CC(C)=CC=C1C(N=C1NC2CCCCC2)=NC2=C1CCC2 PPRZHPKKDVNLTJ-UHFFFAOYSA-N 0.000 claims description 2
- MQXYGWJHOABDIK-UHFFFAOYSA-N n-cyclopentyl-2-(3,4-dimethoxyphenyl)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-amine Chemical compound C1=C(OC)C(OC)=CC=C1C(N=C1NC2CCCC2)=NC2=C1CCC2 MQXYGWJHOABDIK-UHFFFAOYSA-N 0.000 claims description 2
- XOTUXHUSCXTYQE-UHFFFAOYSA-N n-cyclopentyl-2-(3,5-dichlorophenyl)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-amine Chemical compound ClC1=CC(Cl)=CC(C=2N=C(NC3CCCC3)C=3CCCC=3N=2)=C1 XOTUXHUSCXTYQE-UHFFFAOYSA-N 0.000 claims description 2
- HHYMRWQLZNNEGY-UHFFFAOYSA-N n-cyclopentyl-2-(4-methoxyphenyl)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1C(N=C1NC2CCCC2)=NC2=C1CCC2 HHYMRWQLZNNEGY-UHFFFAOYSA-N 0.000 claims description 2
- ZGRLBUXNONOKGU-UHFFFAOYSA-N n-cyclopentyl-2-(4-methylphenyl)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-amine Chemical compound C1=CC(C)=CC=C1C(N=C1NC2CCCC2)=NC2=C1CCC2 ZGRLBUXNONOKGU-UHFFFAOYSA-N 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
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- 208000007278 renal glycosuria Diseases 0.000 claims description 2
- 208000037803 restenosis Diseases 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 claims 1
- PHUWLVRHWFFLJZ-UHFFFAOYSA-N 2-(3-chlorophenyl)-n-[2-(3-methoxyphenyl)ethyl]-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-amine Chemical compound COC1=CC=CC(CCNC=2C=3CCCC=3N=C(N=2)C=2C=C(Cl)C=CC=2)=C1 PHUWLVRHWFFLJZ-UHFFFAOYSA-N 0.000 claims 1
- ISSNZDSDJWQCPL-UHFFFAOYSA-N 2-(4-chlorophenyl)-n-[2-(3-methoxyphenyl)ethyl]-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-amine Chemical compound COC1=CC=CC(CCNC=2C=3CCCC=3N=C(N=2)C=2C=CC(Cl)=CC=2)=C1 ISSNZDSDJWQCPL-UHFFFAOYSA-N 0.000 claims 1
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 239000012190 activator Substances 0.000 claims 1
- 208000030603 inherited susceptibility to asthma Diseases 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- 125000005505 thiomorpholino group Chemical group 0.000 claims 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 125000006763 (C3-C9) cycloalkyl group Chemical group 0.000 abstract 1
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- 150000003254 radicals Chemical class 0.000 description 39
- ZOOGRGPOEVQQDX-UUOKFMHZSA-N 3',5'-cyclic GMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 description 23
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- 230000000694 effects Effects 0.000 description 12
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- 230000004913 activation Effects 0.000 description 11
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
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- 239000002904 solvent Substances 0.000 description 6
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- 125000004432 carbon atom Chemical group C* 0.000 description 4
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
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- 230000000144 pharmacologic effect Effects 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 150000003230 pyrimidines Chemical group 0.000 description 4
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A61P3/00—Drugs for disorders of the metabolism
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- A—HUMAN NECESSITIES
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- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
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- A—HUMAN NECESSITIES
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Reproductive Health (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19853278 | 1998-11-19 | ||
| DE19853278A DE19853278A1 (de) | 1998-11-19 | 1998-11-19 | Substituierte 4-Amino-2-aryl-cyclopenta[d]pyrimidine, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2257103T3 true ES2257103T3 (es) | 2006-07-16 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES99972626T Expired - Lifetime ES2257103T3 (es) | 1998-11-19 | 1999-11-03 | 4-amino-2-aril-ciclopenta(d)pirimidinas sustituidas, su preparacion, su uso y preparados farmaceuticos que las contienen. |
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| Country | Link |
|---|---|
| US (2) | US6627628B1 (enExample) |
| EP (1) | EP1131302B1 (enExample) |
| JP (1) | JP4695262B2 (enExample) |
| AT (1) | ATE316964T1 (enExample) |
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| CA (1) | CA2351488C (enExample) |
| DE (2) | DE19853278A1 (enExample) |
| ES (1) | ES2257103T3 (enExample) |
| PT (1) | PT1131302E (enExample) |
| WO (1) | WO2000031047A1 (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19853278A1 (de) * | 1998-11-19 | 2000-05-25 | Aventis Pharma Gmbh | Substituierte 4-Amino-2-aryl-cyclopenta[d]pyrimidine, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate |
| DE19904710A1 (de) | 1999-02-05 | 2000-08-10 | Aventis Pharma Gmbh | Substituierte 4-Amino-2-aryl-tetrahydrochinazoline, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate |
| US7031977B2 (en) * | 2002-02-28 | 2006-04-18 | Plumtree Software, Inc. | Efficiently storing indented threads in a threaded discussion application |
| AU2003288994A1 (en) * | 2002-12-10 | 2004-06-30 | Ono Pharmaceutical Co., Ltd. | Nitrogen-containing heterocyclic compounds and medicinal use thereof |
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|---|---|---|---|---|
| US3346452A (en) | 1963-08-19 | 1967-10-10 | Ciba Geigy Corp | 5, 6-lower alkylene-pyrimidines |
| DE4029654A1 (de) | 1990-09-19 | 1992-04-02 | Hoechst Ag | 2-phenyl-pyrimidine, verfahren zu ihrer herstellung, sie enthaltende mittel und ihre verwendung als fungizide |
| JP2928079B2 (ja) | 1994-02-14 | 1999-07-28 | 永信薬品工業股▲ふん▼有限公司 | １−（置換ベンジル）−３−（置換アリール）縮合ピラゾール類、その製造法及びその用途 |
| JPH07228573A (ja) * | 1994-02-16 | 1995-08-29 | Dainippon Pharmaceut Co Ltd | ２−フェニルシクロアルカノピリミジン誘導体 |
| IL117659A (en) | 1995-04-13 | 2000-12-06 | Dainippon Pharmaceutical Co | Substituted 2-phenyl pyrimidino amino acetamide derivative process for preparing the same and a pharmaceutical composition containing same |
| WO1997047601A1 (en) | 1996-06-11 | 1997-12-18 | Yoshitomi Pharmaceutical Industries, Ltd. | Fused heterocyclic compounds and medicinal uses thereof |
| DE19642255A1 (de) | 1996-10-14 | 1998-04-16 | Bayer Ag | Verwendung von 1-Benzyl-3-(substituierten-hetaryl) -kondensierten Pyrazol-Derivaten |
| EP0934311B1 (de) | 1996-10-14 | 2009-05-13 | Bayer HealthCare AG | Neue heterocyclylmethyl-substituierte pyrazolderivate und ihre verwendung in der behandlung von herz-kreislauf-erkrankungen |
| DE19836697A1 (de) | 1998-08-13 | 2000-02-17 | Hoechst Marion Roussel De Gmbh | Substituierte 4-Amino-2-aryl-pyrimidine, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate |
| DE19853278A1 (de) * | 1998-11-19 | 2000-05-25 | Aventis Pharma Gmbh | Substituierte 4-Amino-2-aryl-cyclopenta[d]pyrimidine, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate |
-
1998
- 1998-11-19 DE DE19853278A patent/DE19853278A1/de not_active Withdrawn
-
1999
- 1999-11-03 ES ES99972626T patent/ES2257103T3/es not_active Expired - Lifetime
- 1999-11-03 CA CA002351488A patent/CA2351488C/en not_active Expired - Fee Related
- 1999-11-03 US US09/856,069 patent/US6627628B1/en not_active Expired - Lifetime
- 1999-11-03 WO PCT/EP1999/008382 patent/WO2000031047A1/de not_active Ceased
- 1999-11-03 JP JP2000583875A patent/JP4695262B2/ja not_active Expired - Fee Related
- 1999-11-03 AU AU11594/00A patent/AU1159400A/en not_active Abandoned
- 1999-11-03 AT AT99972626T patent/ATE316964T1/de active
- 1999-11-03 EP EP99972626A patent/EP1131302B1/de not_active Expired - Lifetime
- 1999-11-03 PT PT99972626T patent/PT1131302E/pt unknown
- 1999-11-03 DE DE59913103T patent/DE59913103D1/de not_active Expired - Lifetime
-
2003
- 2003-09-12 US US10/660,489 patent/US7138398B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| PT1131302E (pt) | 2006-05-31 |
| JP2002530385A (ja) | 2002-09-17 |
| CA2351488A1 (en) | 2000-06-02 |
| AU1159400A (en) | 2000-06-13 |
| US6627628B1 (en) | 2003-09-30 |
| ATE316964T1 (de) | 2006-02-15 |
| US20040048850A1 (en) | 2004-03-11 |
| DE59913103D1 (de) | 2006-04-13 |
| EP1131302A1 (de) | 2001-09-12 |
| CA2351488C (en) | 2009-12-29 |
| DE19853278A1 (de) | 2000-05-25 |
| JP4695262B2 (ja) | 2011-06-08 |
| WO2000031047A1 (de) | 2000-06-02 |
| EP1131302B1 (de) | 2006-02-01 |
| US7138398B2 (en) | 2006-11-21 |
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