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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- 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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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
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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)
- General Chemical & Material Sciences (AREA)
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- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
| DE19853278 | 1998-11-19 |
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. |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US6627628B1 (https=) |
| EP (1) | EP1131302B1 (https=) |
| JP (1) | JP4695262B2 (https=) |
| AT (1) | ATE316964T1 (https=) |
| AU (1) | AU1159400A (https=) |
| CA (1) | CA2351488C (https=) |
| DE (2) | DE19853278A1 (https=) |
| ES (1) | ES2257103T3 (https=) |
| PT (1) | PT1131302E (https=) |
| WO (1) | WO2000031047A1 (https=) |
Families Citing this family (25)
| 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 |
| WO2004052862A1 (ja) * | 2002-12-10 | 2004-06-24 | Ono Pharmaceutical Co., Ltd. | 含窒素複素環化合物およびその医薬用途 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| JP3531169B2 (ja) | 1996-06-11 | 2004-05-24 | 三菱ウェルファーマ株式会社 | 縮合ヘテロ環化合物およびその医薬用途 |
| DE19642255A1 (de) | 1996-10-14 | 1998-04-16 | Bayer Ag | Verwendung von 1-Benzyl-3-(substituierten-hetaryl) -kondensierten Pyrazol-Derivaten |
| IL129416A0 (en) | 1996-10-14 | 2000-02-17 | Bayer Ag | New heterocyclylmethyl-substituted pyrazol derivatives |
| 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 DE DE59913103T patent/DE59913103D1/de not_active Expired - Lifetime
- 1999-11-03 AU AU11594/00A patent/AU1159400A/en not_active Abandoned
- 1999-11-03 AT AT99972626T patent/ATE316964T1/de active
- 1999-11-03 US US09/856,069 patent/US6627628B1/en not_active Expired - Lifetime
- 1999-11-03 EP EP99972626A patent/EP1131302B1/de not_active Expired - Lifetime
- 1999-11-03 JP JP2000583875A patent/JP4695262B2/ja not_active Expired - Fee Related
- 1999-11-03 CA CA002351488A patent/CA2351488C/en not_active Expired - Fee Related
- 1999-11-03 ES ES99972626T patent/ES2257103T3/es not_active Expired - Lifetime
- 1999-11-03 WO PCT/EP1999/008382 patent/WO2000031047A1/de not_active Ceased
- 1999-11-03 PT PT99972626T patent/PT1131302E/pt unknown
-
2003
- 2003-09-12 US US10/660,489 patent/US7138398B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| WO2000031047A1 (de) | 2000-06-02 |
| PT1131302E (pt) | 2006-05-31 |
| CA2351488C (en) | 2009-12-29 |
| CA2351488A1 (en) | 2000-06-02 |
| DE59913103D1 (de) | 2006-04-13 |
| US7138398B2 (en) | 2006-11-21 |
| US20040048850A1 (en) | 2004-03-11 |
| EP1131302A1 (de) | 2001-09-12 |
| US6627628B1 (en) | 2003-09-30 |
| JP2002530385A (ja) | 2002-09-17 |
| DE19853278A1 (de) | 2000-05-25 |
| JP4695262B2 (ja) | 2011-06-08 |
| AU1159400A (en) | 2000-06-13 |
| EP1131302B1 (de) | 2006-02-01 |
| ATE316964T1 (de) | 2006-02-15 |
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