ES2211503T3 - 4-amino-2-ariltetrahidroquinazolinas, su preparacion, su uso y composiciones farmaceuticas que las comprenden. - Google Patents
4-amino-2-ariltetrahidroquinazolinas, su preparacion, su uso y composiciones farmaceuticas que las comprenden.Info
- Publication number
- ES2211503T3 ES2211503T3 ES00901586T ES00901586T ES2211503T3 ES 2211503 T3 ES2211503 T3 ES 2211503T3 ES 00901586 T ES00901586 T ES 00901586T ES 00901586 T ES00901586 T ES 00901586T ES 2211503 T3 ES2211503 T3 ES 2211503T3
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- phenyl
- group
- substituted
- substituents
- 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 11
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 76
- 125000001424 substituent group Chemical group 0.000 claims abstract description 70
- -1 (C1-C4) -S (O) m- Chemical group 0.000 claims abstract description 63
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 44
- 150000003839 salts Chemical class 0.000 claims abstract description 44
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 33
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 30
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 27
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 21
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 21
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 20
- 239000000203 mixture Substances 0.000 claims abstract description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
- 239000001257 hydrogen Substances 0.000 claims abstract description 17
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 9
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 52
- 125000003118 aryl group Chemical group 0.000 claims description 28
- 102000007637 Soluble Guanylyl Cyclase Human genes 0.000 claims description 21
- 108010007205 Soluble Guanylyl Cyclase Proteins 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 11
- 238000011321 prophylaxis Methods 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- PKORYTIUMAOPED-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinazoline Chemical group C1=CC=C2NCNCC2=C1 PKORYTIUMAOPED-UHFFFAOYSA-N 0.000 claims description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 125000002619 bicyclic group Chemical group 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 206010002383 Angina Pectoris Diseases 0.000 claims description 4
- 201000001320 Atherosclerosis 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
- 125000004429 atom Chemical group 0.000 claims description 4
- RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 claims description 4
- 238000011282 treatment Methods 0.000 claims description 4
- 125000006763 (C3-C9) cycloalkyl group Chemical group 0.000 claims description 3
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 3
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 3
- 241000790917 Dioxys <bee> Species 0.000 claims description 3
- 206010048554 Endothelial dysfunction Diseases 0.000 claims description 3
- 208000010228 Erectile Dysfunction Diseases 0.000 claims description 3
- 206010019280 Heart failures Diseases 0.000 claims description 3
- 206010020772 Hypertension Diseases 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 230000008694 endothelial dysfunction Effects 0.000 claims description 3
- 201000001881 impotence Diseases 0.000 claims description 3
- 208000010125 myocardial infarction Diseases 0.000 claims description 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
- WUAQCTPWWDBLQC-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinazolin-4-ol Chemical compound C1=CC=C2C(O)NCNC2=C1 WUAQCTPWWDBLQC-UHFFFAOYSA-N 0.000 claims description 2
- 206010052337 Diastolic dysfunction Diseases 0.000 claims description 2
- 208000011514 Familial renal glucosuria Diseases 0.000 claims description 2
- 230000003213 activating effect Effects 0.000 claims description 2
- 208000006673 asthma Diseases 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 208000020832 chronic kidney disease Diseases 0.000 claims description 2
- 208000022831 chronic renal failure syndrome Diseases 0.000 claims description 2
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 2
- 208000030603 inherited susceptibility to asthma Diseases 0.000 claims description 2
- 210000004185 liver Anatomy 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229940127557 pharmaceutical product Drugs 0.000 claims description 2
- 208000002815 pulmonary hypertension Diseases 0.000 claims description 2
- 208000007278 renal glycosuria Diseases 0.000 claims description 2
- 208000037803 restenosis Diseases 0.000 claims description 2
- 206010016654 Fibrosis Diseases 0.000 claims 1
- 239000012190 activator Substances 0.000 claims 1
- 230000007882 cirrhosis Effects 0.000 claims 1
- 125000005505 thiomorpholino group Chemical group 0.000 claims 1
- 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- ZOOGRGPOEVQQDX-KHLHZJAASA-N cyclic guanosine monophosphate Chemical compound C([C@H]1O2)O[P@](O)(=O)O[C@@H]1[C@H](O)[C@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-KHLHZJAASA-N 0.000 description 22
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- 238000012360 testing method Methods 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- 238000002560 therapeutic procedure Methods 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
- 230000004913 activation Effects 0.000 description 8
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
- 230000000638 stimulation Effects 0.000 description 8
- 239000003981 vehicle Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 7
- 239000003814 drug Substances 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 108010078321 Guanylate Cyclase Proteins 0.000 description 6
- 102000014469 Guanylate cyclase Human genes 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 125000002950 monocyclic group Chemical group 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- SRROXLOSEVNFJD-UHFFFAOYSA-N 4-(4-oxo-5,6,7,8-tetrahydro-1h-quinazolin-2-yl)benzamide Chemical compound C1=CC(C(=O)N)=CC=C1C1=NC(O)=C(CCCC2)C2=N1 SRROXLOSEVNFJD-UHFFFAOYSA-N 0.000 description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- 150000001409 amidines Chemical class 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000002757 morpholinyl group Chemical group 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 230000001575 pathological effect Effects 0.000 description 4
- 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
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 3
- GZIUJOOLOPRYRY-UHFFFAOYSA-N 4-chloro-2-(4-chlorophenyl)-5,6,7,8-tetrahydroquinazoline Chemical compound C1=CC(Cl)=CC=C1C1=NC(Cl)=C(CCCC2)C2=N1 GZIUJOOLOPRYRY-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-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
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- XKMLYUALXHKNFT-UUOKFMHZSA-N Guanosine-5'-triphosphate Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XKMLYUALXHKNFT-UUOKFMHZSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 3
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 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 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
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- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 3
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 2
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- DZBHVWLQTPYPOW-UHFFFAOYSA-N 1-hydroxy-3,4-dihydro-2h-quinazoline Chemical compound C1=CC=C2N(O)CNCC2=C1 DZBHVWLQTPYPOW-UHFFFAOYSA-N 0.000 description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 2
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- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
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- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 238000011161 development Methods 0.000 description 2
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Classifications
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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
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/94—Nitrogen atoms
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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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- A—HUMAN NECESSITIES
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- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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- A—HUMAN NECESSITIES
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- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- 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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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Heart & Thoracic Surgery (AREA)
- Pulmonology (AREA)
- Cardiology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Urology & Nephrology (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Vascular Medicine (AREA)
- Obesity (AREA)
- Emergency Medicine (AREA)
- Reproductive Health (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19904710 | 1999-02-05 | ||
| DE19904710A DE19904710A1 (de) | 1999-02-05 | 1999-02-05 | Substituierte 4-Amino-2-aryl-tetrahydrochinazoline, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2211503T3 true ES2211503T3 (es) | 2004-07-16 |
Family
ID=7896548
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES00901586T Expired - Lifetime ES2211503T3 (es) | 1999-02-05 | 2000-01-22 | 4-amino-2-ariltetrahidroquinazolinas, su preparacion, su uso y composiciones farmaceuticas que las comprenden. |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US6660746B1 (enExample) |
| EP (1) | EP1150963B1 (enExample) |
| JP (1) | JP4700194B2 (enExample) |
| AT (1) | ATE255565T1 (enExample) |
| AU (1) | AU2292900A (enExample) |
| CA (1) | CA2362363C (enExample) |
| DE (2) | DE19904710A1 (enExample) |
| DK (1) | DK1150963T3 (enExample) |
| ES (1) | ES2211503T3 (enExample) |
| PT (1) | PT1150963E (enExample) |
| WO (1) | WO2000046214A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| WO2001032632A2 (en) * | 1999-11-01 | 2001-05-10 | Eli Lilly And Company | Pharmaceutically active 4-substituted pyrimidine derivatives |
| 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 |
| JP4895806B2 (ja) * | 2003-04-09 | 2012-03-14 | エクセリクシス， インク． | Ｔｉｅ−２モジュレータと使用方法 |
| EP1663994B1 (en) * | 2003-08-05 | 2012-03-07 | Vertex Pharmaceuticals Incorporated | Tetrahydroquinazoline compounds as inhibitors of voltage-gated ion channels |
| WO2006023844A2 (en) * | 2004-08-20 | 2006-03-02 | Entremed, Inc. | Compositions and methods comprising proteinase activated receptor antagonists |
| TW200621257A (en) | 2004-10-20 | 2006-07-01 | Astellas Pharma Inc | Pyrimidine derivative fused with nonaromatic ring |
| EP2373317B1 (en) * | 2008-11-25 | 2016-12-14 | Merck Sharp & Dohme Corp. | 4-amino-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one or 4-amino-5,8-dihydropyrido[2,3-d]pyrimidin-7(6H)-one derivatives as activators of the soluble guanylat cyclase for the treatment of cardiovascular diseases |
| EP2549875B1 (en) | 2010-03-25 | 2015-05-13 | Merck Sharp & Dohme Corp. | Soluble guanylate cyclase activators |
| MA34330B1 (fr) | 2010-05-27 | 2013-06-01 | Merck Sharp & Dohme | Activateurs de guanylate cyclase soluble |
| CN113880859B (zh) * | 2021-11-16 | 2022-06-21 | 江西科技师范大学 | 2-芳基-4-芳甲胺基嘧啶类化合物及其应用 |
| TW202435887A (zh) * | 2023-03-01 | 2024-09-16 | 瑞士商諾華公司 | 用於治療疾病或障礙的氫喹唑啉衍生物 |
| WO2025129076A1 (en) * | 2023-12-15 | 2025-06-19 | Eikon Therapeutics, Inc. | Pyridopyrimidine and quinazoline derivatives as usp1 inhibitors, compositions comprising them and methods of using the same |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3346452A (en) * | 1963-08-19 | 1967-10-10 | Ciba Geigy Corp | 5, 6-lower alkylene-pyrimidines |
| US4306065A (en) * | 1979-12-19 | 1981-12-15 | A. H. Robins Company, Incorporated | 2-Aryl-4-substituted quinazolines |
| DE3315424A1 (de) * | 1983-04-28 | 1984-12-20 | Cassella Ag, 6000 Frankfurt | Substituierte piperazin-1-yl-essigsaeure-amide, verfahren zu ihrer herstellung und ihre verwendung |
| DE3922735A1 (de) * | 1989-07-11 | 1991-01-24 | Hoechst Ag | Aminopyrimidin-derivate, verfahren zu ihrer herstellung, sie enthaltende mittel und ihre verwendung als fungizide |
| 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 |
| JP2657760B2 (ja) * | 1992-07-15 | 1997-09-24 | 小野薬品工業株式会社 | ４−アミノキナゾリン誘導体およびそれを含有する医薬品 |
| 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 |
| JPH1087492A (ja) * | 1996-06-25 | 1998-04-07 | Ono Pharmaceut Co Ltd | 一酸化窒素産生阻害剤 |
| JPH10130150A (ja) * | 1996-09-05 | 1998-05-19 | Dainippon Pharmaceut Co Ltd | 酢酸アミド誘導体からなる医薬 |
| TR199901174T2 (xx) | 1996-10-14 | 1999-08-23 | Bayer Aktiengesellschaft | Yeni heterosiklilmetil-ikameli pirazol t�revleri. |
| DE19642255A1 (de) | 1996-10-14 | 1998-04-16 | Bayer Ag | Verwendung von 1-Benzyl-3-(substituierten-hetaryl) -kondensierten Pyrazol-Derivaten |
| US6245760B1 (en) * | 1997-05-28 | 2001-06-12 | Aventis Pharmaceuticals Products, Inc | Quinoline and quinoxaline compounds which inhibit platelet-derived growth factor and/or p56lck tyrosine kinases |
| 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 |
| 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 |
| DE19906037A1 (de) | 1999-02-12 | 2000-08-31 | Trw Automotive Electron & Comp | Schalter, insbesondere Kfz-Bremslichtschalter |
-
1999
- 1999-02-05 DE DE19904710A patent/DE19904710A1/de not_active Withdrawn
-
2000
- 2000-01-22 DE DE2000606936 patent/DE60006936T2/de not_active Expired - Lifetime
- 2000-01-22 ES ES00901586T patent/ES2211503T3/es not_active Expired - Lifetime
- 2000-01-22 AT AT00901586T patent/ATE255565T1/de active
- 2000-01-22 EP EP00901586A patent/EP1150963B1/en not_active Expired - Lifetime
- 2000-01-22 JP JP2000597284A patent/JP4700194B2/ja not_active Expired - Fee Related
- 2000-01-22 WO PCT/EP2000/000468 patent/WO2000046214A1/en not_active Ceased
- 2000-01-22 PT PT00901586T patent/PT1150963E/pt unknown
- 2000-01-22 AU AU22929/00A patent/AU2292900A/en not_active Abandoned
- 2000-01-22 DK DK00901586T patent/DK1150963T3/da active
- 2000-01-22 CA CA002362363A patent/CA2362363C/en not_active Expired - Fee Related
- 2000-02-04 US US09/497,723 patent/US6660746B1/en not_active Expired - Lifetime
-
2003
- 2003-10-01 US US10/674,350 patent/US7045526B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US7045526B2 (en) | 2006-05-16 |
| US20040063690A1 (en) | 2004-04-01 |
| DE60006936D1 (de) | 2004-01-15 |
| JP4700194B2 (ja) | 2011-06-15 |
| CA2362363C (en) | 2009-09-15 |
| CA2362363A1 (en) | 2000-08-10 |
| PT1150963E (pt) | 2004-04-30 |
| US6660746B1 (en) | 2003-12-09 |
| EP1150963A1 (en) | 2001-11-07 |
| DE60006936T2 (de) | 2004-11-18 |
| DK1150963T3 (da) | 2004-04-05 |
| ATE255565T1 (de) | 2003-12-15 |
| WO2000046214A1 (en) | 2000-08-10 |
| EP1150963B1 (en) | 2003-12-03 |
| JP2002536369A (ja) | 2002-10-29 |
| AU2292900A (en) | 2000-08-25 |
| DE19904710A1 (de) | 2000-08-10 |
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