AU733967B2 - Use of 1-benzyl-3-(substituted hetaryl)-fused pyrazole derivatives for the treatment of specific disorders of the cardiovascular system and of the central nervous system - Google Patents
Use of 1-benzyl-3-(substituted hetaryl)-fused pyrazole derivatives for the treatment of specific disorders of the cardiovascular system and of the central nervous system Download PDFInfo
- Publication number
- AU733967B2 AU733967B2 AU50494/98A AU5049498A AU733967B2 AU 733967 B2 AU733967 B2 AU 733967B2 AU 50494/98 A AU50494/98 A AU 50494/98A AU 5049498 A AU5049498 A AU 5049498A AU 733967 B2 AU733967 B2 AU 733967B2
- Authority
- AU
- Australia
- Prior art keywords
- indazole
- hydroxymethylfuran
- compounds
- treatment
- general formula
- 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.)
- Ceased
Links
- 125000001072 heteroaryl group Chemical group 0.000 title claims abstract description 6
- 150000003217 pyrazoles Chemical class 0.000 title claims abstract description 6
- 238000011282 treatment Methods 0.000 title claims description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 9
- 210000003169 central nervous system Anatomy 0.000 title claims description 6
- 210000000748 cardiovascular system Anatomy 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 33
- 239000003814 drug Substances 0.000 claims abstract description 11
- 229940082615 organic nitrates used in cardiac disease Drugs 0.000 claims abstract description 6
- 230000003222 cGMP degradation Effects 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 150000002431 hydrogen Chemical group 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 208000035475 disorder Diseases 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 206010020772 Hypertension Diseases 0.000 claims description 3
- 230000000304 vasodilatating effect Effects 0.000 claims description 3
- VNYQKDRUCYBRRF-UHFFFAOYSA-N [5-[1-[(2-fluorophenyl)methyl]indazol-3-yl]furan-2-yl]methanol Chemical compound O1C(CO)=CC=C1C(C1=CC=CC=C11)=NN1CC1=CC=CC=C1F VNYQKDRUCYBRRF-UHFFFAOYSA-N 0.000 claims description 2
- 206010008118 cerebral infarction Diseases 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims 3
- OQJBIAYSKVCHAG-UHFFFAOYSA-N 1-benzyl-3-(5-methylfuran-2-yl)indazole Chemical compound O1C(C)=CC=C1C(C1=CC=CC=C11)=NN1CC1=CC=CC=C1 OQJBIAYSKVCHAG-UHFFFAOYSA-N 0.000 claims 1
- UZKSWGNDBSTBTO-UHFFFAOYSA-N [5-(1-benzylindazol-3-yl)thiophen-2-yl]methanol Chemical compound S1C(CO)=CC=C1C(C1=CC=CC=C11)=NN1CC1=CC=CC=C1 UZKSWGNDBSTBTO-UHFFFAOYSA-N 0.000 claims 1
- SBSWTXYEELJKOE-UHFFFAOYSA-N [5-[1-[(2-methoxyphenyl)methyl]indazol-3-yl]furan-2-yl]methanol Chemical compound COC1=CC=CC=C1CN1C2=CC=CC=C2C(C=2OC(CO)=CC=2)=N1 SBSWTXYEELJKOE-UHFFFAOYSA-N 0.000 claims 1
- AFQPZJNVLVZLRY-UHFFFAOYSA-N [5-[1-[(3-chlorophenyl)methyl]-6-fluoroindazol-3-yl]furan-2-yl]methanol Chemical compound O1C(CO)=CC=C1C(C1=CC=C(F)C=C11)=NN1CC1=CC=CC(Cl)=C1 AFQPZJNVLVZLRY-UHFFFAOYSA-N 0.000 claims 1
- BOGHNKVXVMGVNX-UHFFFAOYSA-N [5-[1-[(3-chlorophenyl)methyl]indazol-3-yl]furan-2-yl]methanol Chemical compound O1C(CO)=CC=C1C(C1=CC=CC=C11)=NN1CC1=CC=CC(Cl)=C1 BOGHNKVXVMGVNX-UHFFFAOYSA-N 0.000 claims 1
- TXWOCCDCAZBWCH-UHFFFAOYSA-N [5-[1-[(3-fluorophenyl)methyl]indazol-3-yl]furan-2-yl]methanol Chemical compound O1C(CO)=CC=C1C(C1=CC=CC=C11)=NN1CC1=CC=CC(F)=C1 TXWOCCDCAZBWCH-UHFFFAOYSA-N 0.000 claims 1
- NBDLYMCNFMITLQ-UHFFFAOYSA-N [5-[1-[(3-methoxyphenyl)methyl]indazol-3-yl]furan-2-yl]methanol Chemical compound COC1=CC=CC(CN2C3=CC=CC=C3C(C=3OC(CO)=CC=3)=N2)=C1 NBDLYMCNFMITLQ-UHFFFAOYSA-N 0.000 claims 1
- CIFZBDXXMUYOBZ-UHFFFAOYSA-N [5-[1-[(4-fluorophenyl)methyl]indazol-3-yl]furan-2-yl]methanol Chemical compound O1C(CO)=CC=C1C(C1=CC=CC=C11)=NN1CC1=CC=C(F)C=C1 CIFZBDXXMUYOBZ-UHFFFAOYSA-N 0.000 claims 1
- MZNGWBFQIOFOBP-UHFFFAOYSA-N [5-[5-fluoro-1-[(2-fluorophenyl)methyl]indazol-3-yl]furan-2-yl]methanol Chemical compound O1C(CO)=CC=C1C(C1=CC(F)=CC=C11)=NN1CC1=CC=CC=C1F MZNGWBFQIOFOBP-UHFFFAOYSA-N 0.000 claims 1
- NFRFRFNFBKSHGU-UHFFFAOYSA-N [5-[6-fluoro-1-[(2-fluorophenyl)methyl]indazol-3-yl]furan-2-yl]methanol Chemical compound O1C(CO)=CC=C1C(C1=CC=C(F)C=C11)=NN1CC1=CC=CC=C1F NFRFRFNFBKSHGU-UHFFFAOYSA-N 0.000 claims 1
- HFOMHMBCUMTCDT-UHFFFAOYSA-N [5-[6-fluoro-1-[(3-methoxyphenyl)methyl]indazol-3-yl]furan-2-yl]methanol Chemical compound COC1=CC=CC(CN2C3=CC(F)=CC=C3C(C=3OC(CO)=CC=3)=N2)=C1 HFOMHMBCUMTCDT-UHFFFAOYSA-N 0.000 claims 1
- 229940124549 vasodilator Drugs 0.000 abstract description 2
- 239000003071 vasodilator agent Substances 0.000 abstract description 2
- 239000000126 substance Substances 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
- 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 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- 208000006011 Stroke Diseases 0.000 description 4
- 210000000709 aorta Anatomy 0.000 description 4
- XEYBHCRIKKKOSS-UHFFFAOYSA-N disodium;azanylidyneoxidanium;iron(2+);pentacyanide Chemical compound [Na+].[Na+].[Fe+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].[O+]#N XEYBHCRIKKKOSS-UHFFFAOYSA-N 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229940083618 sodium nitroprusside Drugs 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 230000036772 blood pressure Effects 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 238000011835 investigation Methods 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 206010002383 Angina Pectoris Diseases 0.000 description 2
- 206010003210 Arteriosclerosis Diseases 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 206010019280 Heart failures Diseases 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 208000011775 arteriosclerosis disease Diseases 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 238000009530 blood pressure measurement Methods 0.000 description 2
- 230000002490 cerebral effect Effects 0.000 description 2
- 230000008602 contraction Effects 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 210000002889 endothelial cell Anatomy 0.000 description 2
- -1 for example Chemical class 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 208000010125 myocardial infarction Diseases 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- SONNWYBIRXJNDC-VIFPVBQESA-N phenylephrine Chemical compound CNC[C@H](O)C1=CC=CC(O)=C1 SONNWYBIRXJNDC-VIFPVBQESA-N 0.000 description 2
- 229960001802 phenylephrine Drugs 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000000638 stimulation Effects 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 230000002883 vasorelaxation effect Effects 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- NCGICGYLBXGBGN-UHFFFAOYSA-N 3-morpholin-4-yl-1-oxa-3-azonia-2-azanidacyclopent-3-en-5-imine;hydrochloride Chemical compound Cl.[N-]1OC(=N)C=[N+]1N1CCOCC1 NCGICGYLBXGBGN-UHFFFAOYSA-N 0.000 description 1
- XATBTRGIZVKLLZ-UHFFFAOYSA-N 5-[1-[(2-fluorophenyl)methyl]indazol-3-yl]furan-2-carbaldehyde Chemical compound FC1=CC=CC=C1CN1C2=CC=CC=C2C(C=2OC(C=O)=CC=2)=N1 XATBTRGIZVKLLZ-UHFFFAOYSA-N 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 206010008120 Cerebral ischaemia Diseases 0.000 description 1
- 206010008190 Cerebrovascular accident Diseases 0.000 description 1
- 102000029816 Collagenase Human genes 0.000 description 1
- 108060005980 Collagenase Proteins 0.000 description 1
- 208000020401 Depressive disease Diseases 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 108010078321 Guanylate Cyclase Proteins 0.000 description 1
- 102000014469 Guanylate cyclase Human genes 0.000 description 1
- 206010019196 Head injury Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- 241001484259 Lacuna Species 0.000 description 1
- 208000020358 Learning disease Diseases 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 208000026139 Memory disease Diseases 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 1
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- 201000001880 Sexual dysfunction Diseases 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- IUJDSEJGGMCXSG-UHFFFAOYSA-N Thiopental Chemical compound CCCC(C)C1(CC)C(=O)NC(=S)NC1=O IUJDSEJGGMCXSG-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000002744 anti-aggregatory effect Effects 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000004087 circulation Effects 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 230000007278 cognition impairment Effects 0.000 description 1
- 229960002424 collagenase Drugs 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000003511 endothelial effect Effects 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical compound CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 210000001105 femoral artery Anatomy 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 229960003711 glyceryl trinitrate Drugs 0.000 description 1
- 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 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- MOYKHGMNXAOIAT-JGWLITMVSA-N isosorbide dinitrate Chemical compound [O-][N+](=O)O[C@H]1CO[C@@H]2[C@H](O[N+](=O)[O-])CO[C@@H]21 MOYKHGMNXAOIAT-JGWLITMVSA-N 0.000 description 1
- 229960000201 isosorbide dinitrate Drugs 0.000 description 1
- YWXYYJSYQOXTPL-SLPGGIOYSA-N isosorbide mononitrate Chemical compound [O-][N+](=O)O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 YWXYYJSYQOXTPL-SLPGGIOYSA-N 0.000 description 1
- 229960003827 isosorbide mononitrate Drugs 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 201000003723 learning disability Diseases 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- YLGXILFCIXHCMC-JHGZEJCSSA-N methyl cellulose Chemical compound COC1C(OC)C(OC)C(COC)O[C@H]1O[C@H]1C(OC)C(OC)C(OC)OC1COC YLGXILFCIXHCMC-JHGZEJCSSA-N 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- XLFWDASMENKTKL-UHFFFAOYSA-N molsidomine Chemical compound O1C(N=C([O-])OCC)=C[N+](N2CCOCC2)=N1 XLFWDASMENKTKL-UHFFFAOYSA-N 0.000 description 1
- 229960004027 molsidomine Drugs 0.000 description 1
- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
- 239000002840 nitric oxide donor Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 235000019701 semiluxury food Nutrition 0.000 description 1
- 231100000872 sexual dysfunction Toxicity 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 208000019116 sleep disease Diseases 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229960003279 thiopental Drugs 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 230000001196 vasorelaxation Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
- A61K31/416—1,2-Diazoles condensed with carbocyclic ring systems, e.g. indazole
-
- 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
-
- 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
-
- 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
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
-
- 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
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Epidemiology (AREA)
- Biomedical Technology (AREA)
- Hospice & Palliative Care (AREA)
- Vascular Medicine (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19642255 | 1996-10-14 | ||
| DE19642255A DE19642255A1 (de) | 1996-10-14 | 1996-10-14 | Verwendung von 1-Benzyl-3-(substituierten-hetaryl) -kondensierten Pyrazol-Derivaten |
| PCT/EP1997/005381 WO1998016223A1 (de) | 1996-10-14 | 1997-10-01 | Verwendung von 1-benzyl-3-(substituiertes-hetaryl)-kondensierten pyrazol-derivaten zur belandlung von speziellen erkrankungen des herz-kreislaufsystems und des zentralnervensystems |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU5049498A AU5049498A (en) | 1998-05-11 |
| AU733967B2 true AU733967B2 (en) | 2001-05-31 |
Family
ID=7808650
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU50494/98A Ceased AU733967B2 (en) | 1996-10-14 | 1997-10-01 | Use of 1-benzyl-3-(substituted hetaryl)-fused pyrazole derivatives for the treatment of specific disorders of the cardiovascular system and of the central nervous system |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US6180656B1 (enExample) |
| EP (1) | EP0932403B1 (enExample) |
| JP (2) | JP2001502318A (enExample) |
| AT (1) | ATE311184T1 (enExample) |
| AU (1) | AU733967B2 (enExample) |
| BR (1) | BR9712304A (enExample) |
| CA (1) | CA2268314C (enExample) |
| CZ (1) | CZ129299A3 (enExample) |
| DE (2) | DE19642255A1 (enExample) |
| EE (1) | EE9900156A (enExample) |
| ES (1) | ES2252777T3 (enExample) |
| HU (1) | HUP9903885A3 (enExample) |
| ID (1) | ID22162A (enExample) |
| IL (1) | IL129318A (enExample) |
| NO (1) | NO991685D0 (enExample) |
| NZ (1) | NZ335091A (enExample) |
| PL (1) | PL332719A1 (enExample) |
| SK (1) | SK46599A3 (enExample) |
| TR (1) | TR199900782T2 (enExample) |
| TW (1) | TW442482B (enExample) |
| WO (1) | WO1998016223A1 (enExample) |
Families Citing this family (119)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19744026A1 (de) | 1997-10-06 | 1999-04-08 | Hoechst Marion Roussel De Gmbh | Pyrazol-Derivate, ihre Herstellung und ihre Verwendung in Arzneimitteln |
| DE19846514A1 (de) * | 1998-10-09 | 2000-04-20 | Bayer Ag | Neue Heterocyclyl-methyl-substituierte Pyrazole |
| 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 |
| DE19943635A1 (de) * | 1999-09-13 | 2001-03-15 | Bayer Ag | Neuartige Aminodicarbonsäurederivate mit pharmazeutischen Eigenschaften |
| DE19943634A1 (de) | 1999-09-13 | 2001-04-12 | Bayer Ag | Neuartige Dicarbonsäurederivate mit pharmazeutischen Eigenschaften |
| DE19943636A1 (de) | 1999-09-13 | 2001-03-15 | Bayer Ag | Neuartige Dicarbonsäurederivate mit pharmazeutischen Eigenschaften |
| GB0002666D0 (en) | 2000-02-04 | 2000-03-29 | Univ London | Blockade of voltage dependent sodium channels |
| DE10021069A1 (de) * | 2000-04-28 | 2001-10-31 | Bayer Ag | Substituiertes Pyrazolderivat |
| US6387942B2 (en) | 2000-06-19 | 2002-05-14 | Yung Shin Pharmaceutical Ind. Co. Ltd | Method of treating disorders related to protease-activated receptors-induced cell activation |
| KR20020001013A (ko) * | 2000-06-23 | 2002-01-09 | 리팡유 | 트롬빈-유도 혈소판 응집 저해방법 |
| KR20050117594A (ko) * | 2000-06-23 | 2005-12-15 | 주식회사 하이닉스반도체 | 반도체 소자의 제조 방법 |
| DE10054278A1 (de) * | 2000-11-02 | 2002-05-08 | Bayer Ag | Verwendung von Stimulatoren der löslichen Guanylatcyclase zur Behandlung von Osteoporose |
| EP1339716B1 (de) | 2000-11-22 | 2004-11-03 | Bayer HealthCare AG | lactam-substituierte pyrazolopyridinderivate |
| AR031176A1 (es) | 2000-11-22 | 2003-09-10 | Bayer Ag | Nuevos derivados de pirazolpiridina sustituidos con piridina |
| DE10057754A1 (de) | 2000-11-22 | 2002-05-23 | Bayer Ag | Neue Sulfonamid-substituierte Pyrazolopyridinderivate |
| DE10057751A1 (de) * | 2000-11-22 | 2002-05-23 | Bayer Ag | Neue Carbamat-substituierte Pyrazolopyridinderivate |
| US6518294B2 (en) | 2001-01-24 | 2003-02-11 | Yung Shin Pharmaceutical Ind. Co. | Fused pyrazolyl compounds |
| DE10109858A1 (de) | 2001-03-01 | 2002-09-05 | Bayer Ag | Neuartige halogensubstituierte Aminodicarbonsäurederivate |
| DE10109861A1 (de) | 2001-03-01 | 2002-09-05 | Bayer Ag | Neuartige seitenkettenhalogenierte Aminodicarbonsäurederivate |
| DE10109859A1 (de) * | 2001-03-01 | 2002-09-05 | Bayer Ag | Neuartige Aminodicarbonsäurederivate |
| DE10122894A1 (de) * | 2001-05-11 | 2002-11-14 | Bayer Ag | Neue Sulfonat-substituierte Pyrazolopyridinderivate |
| US7049334B2 (en) * | 2001-09-14 | 2006-05-23 | Carlsbad Technology, Inc. | Enhancement of learning and memory and treatment of amnesia |
| US20040077702A1 (en) * | 2001-09-14 | 2004-04-22 | Wen-Mei Fu | Treatment of nuerodegenerative diseases |
| TWI264304B (en) | 2002-01-25 | 2006-10-21 | Yung Shin Pharm Ind Co Ltd | Methods of treating sepsis |
| DE10220570A1 (de) | 2002-05-08 | 2003-11-20 | Bayer Ag | Carbamat-substituierte Pyrazolopyridine |
| AU2004275694B2 (en) * | 2003-06-30 | 2008-03-06 | Bizbiotech Co., Ltd. | Compounds, compositions and methods |
| JP2005089457A (ja) * | 2003-09-03 | 2005-04-07 | Yung Shin Pharmaceutical Industry Co Ltd | 骨成長を促進するまたは骨吸収を阻害するための薬剤組成物 |
| WO2005077005A2 (en) * | 2004-02-04 | 2005-08-25 | The General Hospital Corporation | Enhancing the effectiveness of an inhaled therapeutic gas |
| DE102005050498A1 (de) | 2005-10-21 | 2007-06-06 | Bayer Healthcare Aktiengesellschaft | Cyclopropylessigsäure-Derivate und ihre Verwendung |
| DE102005050376A1 (de) | 2005-10-21 | 2007-05-31 | Bayer Healthcare Ag | Dicarbonsäure-Derivate und ihre Verwendung |
| DE102005050497A1 (de) | 2005-10-21 | 2007-04-26 | Bayer Healthcare Ag | Difluorphenol-Derivate und ihre Verwendung |
| DE102005050375A1 (de) | 2005-10-21 | 2007-04-26 | Bayer Healthcare Ag | Tetrazol-Derivate und ihre Verwendung |
| DE102005050377A1 (de) * | 2005-10-21 | 2007-04-26 | Bayer Healthcare Ag | Heterocyclische Verbindungen und ihre Verwendung |
| DE102006020327A1 (de) * | 2006-04-27 | 2007-12-27 | Bayer Healthcare Ag | Heterocyclisch substituierte, anellierte Pyrazol-Derivate und ihre Verwendung |
| DE102006021733A1 (de) * | 2006-05-09 | 2007-11-22 | Bayer Healthcare Ag | 3-Tetrazolylindazole und 3-Tetrazolylpyrazolopyridine sowie ihre Verwendung |
| DE102006043443A1 (de) | 2006-09-15 | 2008-03-27 | Bayer Healthcare Ag | Neue aza-bicyclische Verbindungen und ihre Verwendung |
| DE102006054757A1 (de) * | 2006-11-21 | 2008-05-29 | Bayer Healthcare Ag | Neue aza-bicyclische Verbindungen und ihre Verwendung |
| DE102007015035A1 (de) | 2007-03-29 | 2008-10-02 | Bayer Healthcare Ag | Substituierte Dibenzoesäure-Derivate und ihre Verwendung |
| DE102007015034A1 (de) | 2007-03-29 | 2008-10-02 | Bayer Healthcare Ag | Lactam-substituierte Dicarbonsäuren und ihre Verwendung |
| WO2008124505A2 (en) * | 2007-04-05 | 2008-10-16 | Ironwood Pharmaceuticals,Inc. | Soluble guanylate cyclase (sgc) modulators for treatment of lipid related disorders |
| US20080252028A1 (en) * | 2007-04-16 | 2008-10-16 | Ming-Tai Huang | Shock absorbing device for toy stroller |
| DE102007026392A1 (de) * | 2007-06-06 | 2008-12-11 | Bayer Healthcare Ag | Lösungen für die Perfusion und Konservierung von Organen und Geweben |
| DE102007028319A1 (de) | 2007-06-20 | 2008-12-24 | Bayer Healthcare Ag | Substituierte Oxazolidinone und ihre Verwendung |
| DE102007028406A1 (de) | 2007-06-20 | 2008-12-24 | Bayer Healthcare Ag | Substituierte Oxazolidinone und ihre Verwendung |
| DE102007028320A1 (de) | 2007-06-20 | 2008-12-24 | Bayer Healthcare Ag | Substituierte Oxazolidinone und ihre Verwendung |
| DE102007028407A1 (de) | 2007-06-20 | 2008-12-24 | Bayer Healthcare Ag | Substituierte Oxazolidinone und ihre Verwendung |
| EP2138178A1 (en) | 2008-06-28 | 2009-12-30 | Bayer Schering Pharma Aktiengesellschaft | Oxazolidninones for the treatment fo chronic obstructive pulmonary disease (COPD) and/or asthma |
| DE102008063992A1 (de) | 2008-12-19 | 2010-09-02 | Lerner, Zinoviy, Dipl.-Ing. | Neue aliphatisch substituierte Pyrazolopyridine und ihre Verwendung |
| DE102009004245A1 (de) | 2009-01-09 | 2010-07-15 | Bayer Schering Pharma Aktiengesellschaft | Neue anellierte, Heteroatom-verbrückte Pyrazol- und Imidazol-Derivate und ihre Verwendung |
| UY33041A (es) | 2009-11-27 | 2011-06-30 | Bayer Schering Pharma Aktienegesellschaft | Procedimiento para la preparaciòn de {4,6-diamino-2-[1-(2-fluorobencil)-1h-pirazolo[3,4-b]piridin-3-il]pirimidin-5-il}carbamato de metilo y su purificaciòn para el uso como principio activo farmacèutico |
| RS59908B1 (sr) | 2009-11-27 | 2020-03-31 | Adverio Pharma Gmbh | Postupak za proizvodnju metil-{4,6-diamino-2-[1-(2-fluorobenzil)-1h-pirazolo[3,4-b]piridin-3-il]pirimidin-5-il}metilkarbamata |
| DE102010021637A1 (de) * | 2010-05-26 | 2011-12-01 | Bayer Schering Pharma Aktiengesellschaft | Substituierte 5-Fluor-1H-Pyrazolopyridine und ihre Verwendung |
| ES2549979T3 (es) * | 2010-05-26 | 2015-11-03 | Adverio Pharma Gmbh | El uso de estimuladores de la sGC, activadores de la sGC, solos y en combinaciones con inhibidores de la PDE5 para el tratamiento de esclerosis sistémica (EcS) |
| EP2585055A1 (de) | 2010-06-25 | 2013-05-01 | Bayer Intellectual Property GmbH | Verwendung von stimulatoren und aktivatoren der löslichen guanylatzyklase zur behandlung von sichelzellanämie und konservierung von blutersatzstoffen |
| DE102010031148A1 (de) | 2010-07-09 | 2012-01-12 | Bayer Schering Pharma Ag | Annellierte 4-Aminopyrimidine und ihre Verwendung |
| DE102010031149A1 (de) | 2010-07-09 | 2012-01-12 | Bayer Schering Pharma Aktiengesellschaft | Annellierte Pyrimidine und Triazine und ihre Verwendung |
| CN103097387B (zh) | 2010-07-09 | 2016-11-02 | 拜耳知识产权有限责任公司 | 环稠合的嘧啶和三嗪以及其用于治疗和/或预防心血管疾病的用途 |
| DE102011007891A1 (de) | 2011-04-21 | 2012-10-25 | Bayer Pharma Aktiengesellschaft | Annellierte 4-Aminopyrimidine und ihre Verwendung |
| KR20130132392A (ko) | 2010-07-09 | 2013-12-04 | 바이엘 인텔렉쳐 프로퍼티 게엠베하 | 가용성 구아닐레이트 시클라제의 자극제로서의 고리-융합된 4-아미노피리미딘 및 그의 용도 |
| DE102011003315A1 (de) | 2011-01-28 | 2012-08-02 | Bayer Schering Pharma Aktiengesellschaft | Annellierte Pyrimindine und Triazine und ihre Verwendung |
| DE102010031667A1 (de) | 2010-07-22 | 2012-01-26 | Bayer Schering Pharma Aktiengesellschaft | Substituierte Methyl-pyrimidin-5-ylcarbamate und ihre Verwendung |
| DE102010031665A1 (de) | 2010-07-22 | 2012-01-26 | Bayer Schering Pharma Aktiengesellschaft | Substituierte Oxazolidinone und Oxazinanone und ihre Verwendung |
| DE102010031666A1 (de) | 2010-07-22 | 2012-01-26 | Bayer Schering Pharma Aktiengesellschaft | Carbamat-substituierte Diaminopyrimidine und ihre Verwendung |
| DE102010040233A1 (de) | 2010-09-03 | 2012-03-08 | Bayer Schering Pharma Aktiengesellschaft | Bicyclische Aza-Heterocyclen und ihre Verwendung |
| DE102010043379A1 (de) | 2010-11-04 | 2012-05-10 | Bayer Schering Pharma Aktiengesellschaft | Substituierte 6-Fluor-1H-Pyrazolo[4,3-b]pyridine und ihre Verwendung |
| DE102010043380A1 (de) | 2010-11-04 | 2012-05-10 | Bayer Schering Pharma Aktiengesellschaft | Benzyl-substituierte Carbamate und ihre Verwendung |
| DE102012200356A1 (de) | 2012-01-11 | 2013-07-11 | Bayer Intellectual Property Gmbh | Substituierte Imidazopyridine und Imidazopyridazine und ihre Verwendung |
| DE102011075399A1 (de) | 2011-05-06 | 2012-11-08 | Bayer Pharma Aktiengesellschaft | Substituierte Imidazopyridine und Imidazopyridazine und ihre Verwendung |
| US20140171434A1 (en) | 2011-01-11 | 2014-06-19 | Bayer Pharma Aktiengessellschaft | Substituted imidazopyridines and imidazopyridazines and the use thereof |
| CN103619845B (zh) | 2011-04-21 | 2016-08-17 | 拜耳知识产权有限责任公司 | 氟烷基取代的吡唑并吡啶及其用途 |
| DE102012200357A1 (de) | 2012-01-11 | 2013-07-11 | Bayer Intellectual Property Gmbh | Fluoralkyl-substituierte Pyrazolopyridine und ihre Verwendung |
| DE102011007890A1 (de) | 2011-04-21 | 2012-10-25 | Bayer Pharma Aktiengesellschaft | Fluoralkyl-substituierte Pyrazolopyridine und ihre Verwendung |
| DE102011075398A1 (de) | 2011-05-06 | 2012-11-08 | Bayer Pharma Aktiengesellschaft | Substituierte Imidazopyridazine und ihre Verwendung |
| DE102012200354A1 (de) | 2012-01-11 | 2013-07-11 | Bayer Intellectual Property Gmbh | Heteroaryl-substituierte Pyrazolopyridine und ihre Verwendung |
| DE102011078715A1 (de) | 2011-07-06 | 2013-01-10 | Bayer Pharma AG | Heteroaryl-substituierte Pyrazolopyridine und ihre Verwendung |
| AU2012280246A1 (en) | 2011-07-06 | 2014-01-23 | Bayer Intellectual Property Gmbh | Heteroaryl-substituted pyrazolopyridines and use thereof as soluble guanylate cyclase stimulators |
| DE102012200351A1 (de) | 2012-01-11 | 2013-07-11 | Bayer Pharma Aktiengesellschaft | Substituierte annellierte Pyrimidine und ihre Verwendung |
| DE102011082041A1 (de) | 2011-09-02 | 2013-03-07 | Bayer Pharma AG | Substituierte annellierte Pyrimidine und ihre Verwendung |
| JP6054967B2 (ja) | 2011-09-02 | 2016-12-27 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | 置換アネレート化ピリミジンおよびその使用 |
| EA030018B1 (ru) | 2011-11-25 | 2018-06-29 | Адверио Фарма Гмбх | Способ получения замещенного 5-фтор-1h-пиразолопиридина |
| DE102012200349A1 (de) | 2012-01-11 | 2013-07-11 | Bayer Intellectual Property Gmbh | Substituierte annellierte Pyrimidine und Triazine und ihre Verwendung |
| DE102012200352A1 (de) | 2012-01-11 | 2013-07-11 | Bayer Intellectual Property Gmbh | Substituierte, annellierte Imidazole und Pyrazole und ihre Verwendung |
| DE102012200360A1 (de) | 2012-01-11 | 2013-07-11 | Bayer Intellectual Property Gmbh | Substituierte Triazine und ihre Verwendung |
| ES2644781T3 (es) | 2012-03-06 | 2017-11-30 | Bayer Intellectual Property Gmbh | Azabiciclos sustituidos y su uso |
| SI2847228T1 (sl) | 2012-05-10 | 2018-11-30 | Bayer Pharma Aktiengesellschaft | Protitelesa zmožna vezave na faktor koagulacije XI in/ali njeno aktivirano obliko faktor XIa in njihove uporabe |
| US9624214B2 (en) | 2012-11-05 | 2017-04-18 | Bayer Pharma Aktiengesellschaft | Amino-substituted imidazo[1,2-a]pyridinecarboxamides and their use |
| US9126998B2 (en) | 2012-11-05 | 2015-09-08 | Bayer Pharma AG | Amino-substituted imidazo[1,2-a]pyridinecarboxamides and their use |
| US8778964B2 (en) | 2012-11-05 | 2014-07-15 | Bayer Pharma Aktiengesellschaft | Hydroxy-substituted imidazo[1,2-a]-pyridinecarboxamides and their use |
| US8796305B2 (en) | 2012-11-05 | 2014-08-05 | Bayer Pharma Aktiengesellschaft | Carboxy-substituted imidazo[1,2-a]pyridinecarboxamides and their use |
| HK1217488A1 (zh) | 2013-02-21 | 2017-01-13 | Adverio Pharma Gmbh | {4,6-二氨基-2-[1-(2-氟苄基)-1h-吡唑并[3,4-b]吡啶-3-基]嘧啶-5-基}甲基氨基甲酸甲酯的形式 |
| KR20150121007A (ko) | 2013-03-01 | 2015-10-28 | 바이엘 파마 악티엔게젤샤프트 | 트리플루오르메틸-치환된 고리-융합된 피리미딘 및 그의 용도 |
| ES2625744T3 (es) * | 2013-06-04 | 2017-07-20 | Bayer Pharma Aktiengesellschaft | Imidazo[1,2-a]piridinas sustituidas con 3-arilo y su uso |
| EP2821071A1 (en) | 2013-07-04 | 2015-01-07 | Institut d'Investigació Biomèdica de Bellvitge (IDIBELL) | Compounds for breast cancer treatment |
| EP3019506A1 (de) | 2013-07-10 | 2016-05-18 | Bayer Pharma Aktiengesellschaft | Benzyl-1h-pyrazolo[3,4-b]pyridine und ihre verwendung |
| EP3024455A1 (en) | 2013-07-25 | 2016-06-01 | Bayer Pharma Aktiengesellschaft | Sgc stimulators or sgc activators and pde5 inhibitors in combination with additional treatment for the therapy of cystic fibrosis |
| WO2015018814A1 (de) | 2013-08-08 | 2015-02-12 | Bayer Pharma Aktiengesellschaft | Substituierte pyrazolo[1,5-a]pyridin-3-carboxamide und ihre verwendung |
| US20160324856A1 (en) | 2014-01-13 | 2016-11-10 | Ironwood Pharmaceuticals, Inc. | Use of sgc stimulators for the treatment of neuromuscular disorders |
| CA2939793A1 (en) | 2014-02-19 | 2015-08-27 | Bayer Pharma Aktiengesellschaft | 3-(pyrimidine-2-yl)imidazo[1,2-a]pyridines |
| WO2015140199A1 (de) | 2014-03-21 | 2015-09-24 | Bayer Pharma Aktiengesellschaft | Cyano-substituierte imidazo[1,2-a]pyridincarboxamide und ihre verwendung |
| EP3137463A1 (de) | 2014-05-02 | 2017-03-08 | Bayer Pharma Aktiengesellschaft | Enantiomere des n-(2-amino-5-fluor-2-methylpentyl)-8-[(2,6-difluorbenzyl)oxy]-2-methylimidazo[1,2-a]pyridin-3-carboxamids sowie der di- and tri-fluor-derivate zur behandlung von kardiovaskulären erkrankungen |
| US10174021B2 (en) | 2014-12-02 | 2019-01-08 | Bayer Pharma Aktiengesellschaft | Substituted pyrazolo[1,5-A]pyridines and their use |
| EP3227287B1 (de) | 2014-12-02 | 2019-08-07 | Bayer Pharma Aktiengesellschaft | Heteroaryl-substituierte imidazo[1,2-a]pyridine und ihre verwendung |
| CN107567451A (zh) | 2015-02-05 | 2018-01-09 | 拜耳制药股份公司 | 作为用于治疗心血管疾病的可溶性鸟苷酸环化酶（sgc）刺激物的n‑取代的8‑[(2,6‑二氟苄基)氧基]‑2,6‑二甲基咪唑并[1,2‑a]吡嗪‑3‑甲酰胺衍生物 |
| US10214526B2 (en) | 2015-02-05 | 2019-02-26 | Bayer Pharma Aktiengesellschaft | Substituted pyrazolo[1,5-a]-pyridine-3-carboxamides and use thereof |
| BR112017023855A2 (pt) | 2015-05-06 | 2018-07-17 | Bayer Pharma Aktiengesellschaft | o uso de estimulantes de sgc, ativadores de scg, em separado e combinações com inibidores de pde5 para o tratamento de úlceras digitais (du) concomitantes à esclerose múltipla (ssc) |
| ES2839248T5 (es) | 2015-07-23 | 2024-02-22 | Bayer Pharma AG | Estimuladores y/o activadores de la guanilatociclasa soluble (sGC) en combinación con un inhibidor de la endopeptidasa neutra (inhibidor de NEP) y/o un antagonista de angiotensina AII y su uso |
| WO2017106175A2 (en) | 2015-12-14 | 2017-06-22 | Ironwood Pharmaceuticals, Inc. | USE OF sGC STIMULATORS FOR THE TREATMENT OF GASTROINTESTINAL SPHINCTER DYSFUNCTION |
| WO2017121700A1 (de) | 2016-01-15 | 2017-07-20 | Bayer Pharma Aktiengesellschaft | 1,3-disubstituierte 1h-pyrazolo[3,4-b]pyridin- derivate und ihre verwendung als stimulatoren der löslichen guanylatcyclase |
| WO2017121693A1 (de) | 2016-01-15 | 2017-07-20 | Bayer Pharma Aktiengesellschaft | Substituierte thiazol- und thiadiazolamide und ihre verwendung |
| WO2017121692A1 (de) | 2016-01-15 | 2017-07-20 | Bayer Pharma Aktiengesellschaft | Substituierte sulfamide und ihre verwendung |
| CN110022871A (zh) | 2016-10-11 | 2019-07-16 | 拜耳制药股份公司 | 包含sGC刺激物和盐皮质激素受体拮抗剂的组合产品 |
| EP3525778A1 (de) | 2016-10-11 | 2019-08-21 | Bayer Pharma Aktiengesellschaft | Kombination enthaltend sgc aktivatoren und mineralocorticoid-rezeptor-antagonisten |
| EP3554488A2 (en) | 2016-12-13 | 2019-10-23 | Cyclerion Therapeutics, Inc. | Use of sgc stimulators for the treatment of esophageal motility disorders |
| WO2018184976A1 (de) | 2017-04-05 | 2018-10-11 | Bayer Pharma Aktiengesellschaft | Substituierte imidazo[1,2-a]pyridincarboxamide und ihre verwendung |
| ES2924359T3 (es) | 2017-04-11 | 2022-10-06 | Sunshine Lake Pharma Co Ltd | Compuestos de indazol sustituidos con flúor y usos de los mismos |
| BR112020022340A2 (pt) | 2018-05-15 | 2021-02-02 | Bayer Aktiengesellschaft | benzamidas substituídas por 1,3-tiazol-2-il para o tratamento de doenças associadas com sensibilização de fibras nervosas |
| MX2021000363A (es) | 2018-07-11 | 2021-04-29 | Cyclerion Therapeutics Inc | Uso de estimuladores de la guanilato ciclasa soluble (sgc) para el tratamiento de trastornos mitocondriales. |
| WO2020164008A1 (en) | 2019-02-13 | 2020-08-20 | Bayer Aktiengesellschaft | Process for the preparation of porous microparticles |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0470039A2 (en) * | 1990-07-30 | 1992-02-05 | H. Lundbeck A/S | Novel 3-arylindole and 3-arylindazole derivatives |
| EP0667345A1 (en) * | 1994-02-14 | 1995-08-16 | Yung Shin Pharm. Ind. Co. Ltd. | 1-Benzyl-3-(substituted aryl)-condensed pyrazole derivatives as inhibitors of platelet aggregation |
-
1996
- 1996-10-14 DE DE19642255A patent/DE19642255A1/de not_active Withdrawn
-
1997
- 1997-10-01 CZ CZ991292A patent/CZ129299A3/cs unknown
- 1997-10-01 AU AU50494/98A patent/AU733967B2/en not_active Ceased
- 1997-10-01 JP JP10517966A patent/JP2001502318A/ja active Pending
- 1997-10-01 ID IDW990187D patent/ID22162A/id unknown
- 1997-10-01 AT AT97913132T patent/ATE311184T1/de not_active IP Right Cessation
- 1997-10-01 NZ NZ335091A patent/NZ335091A/xx unknown
- 1997-10-01 US US09/284,032 patent/US6180656B1/en not_active Expired - Fee Related
- 1997-10-01 BR BR9712304-8A patent/BR9712304A/pt not_active Application Discontinuation
- 1997-10-01 WO PCT/EP1997/005381 patent/WO1998016223A1/de not_active Ceased
- 1997-10-01 CA CA002268314A patent/CA2268314C/en not_active Expired - Fee Related
- 1997-10-01 PL PL97332719A patent/PL332719A1/xx unknown
- 1997-10-01 HU HU9903885A patent/HUP9903885A3/hu unknown
- 1997-10-01 IL IL12931897A patent/IL129318A/en not_active IP Right Cessation
- 1997-10-01 EE EEP199900156A patent/EE9900156A/xx unknown
- 1997-10-01 EP EP97913132A patent/EP0932403B1/de not_active Expired - Lifetime
- 1997-10-01 TR TR1999/00782T patent/TR199900782T2/xx unknown
- 1997-10-01 ES ES97913132T patent/ES2252777T3/es not_active Expired - Lifetime
- 1997-10-01 SK SK465-99A patent/SK46599A3/sk unknown
- 1997-10-01 DE DE59712501T patent/DE59712501D1/de not_active Expired - Lifetime
- 1997-10-14 TW TW086115207A patent/TW442482B/zh not_active IP Right Cessation
-
1999
- 1999-04-09 NO NO991685A patent/NO991685D0/no not_active Application Discontinuation
-
2009
- 2009-02-25 JP JP2009042383A patent/JP2009114205A/ja active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0470039A2 (en) * | 1990-07-30 | 1992-02-05 | H. Lundbeck A/S | Novel 3-arylindole and 3-arylindazole derivatives |
| EP0667345A1 (en) * | 1994-02-14 | 1995-08-16 | Yung Shin Pharm. Ind. Co. Ltd. | 1-Benzyl-3-(substituted aryl)-condensed pyrazole derivatives as inhibitors of platelet aggregation |
Non-Patent Citations (1)
| Title |
|---|
| BLOOD, VOL.87, NO.9, 1 MAY 1996, PAGES 3758-3767 * |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0932403B1 (de) | 2005-11-30 |
| AU5049498A (en) | 1998-05-11 |
| NZ335091A (en) | 2000-09-29 |
| TW442482B (en) | 2001-06-23 |
| TR199900782T2 (xx) | 1999-07-21 |
| IL129318A0 (en) | 2000-02-17 |
| ATE311184T1 (de) | 2005-12-15 |
| EE9900156A (et) | 1999-12-15 |
| HUP9903885A3 (en) | 2000-12-28 |
| NO991685L (no) | 1999-04-09 |
| CA2268314A1 (en) | 1998-04-23 |
| JP2009114205A (ja) | 2009-05-28 |
| BR9712304A (pt) | 1999-08-31 |
| CA2268314C (en) | 2006-12-12 |
| PL332719A1 (en) | 1999-10-11 |
| ID22162A (id) | 1999-09-09 |
| DE59712501D1 (de) | 2006-01-05 |
| JP2001502318A (ja) | 2001-02-20 |
| DE19642255A1 (de) | 1998-04-16 |
| ES2252777T3 (es) | 2006-05-16 |
| EP0932403A1 (de) | 1999-08-04 |
| US6180656B1 (en) | 2001-01-30 |
| IL129318A (en) | 2001-06-14 |
| WO1998016223A1 (de) | 1998-04-23 |
| NO991685D0 (no) | 1999-04-09 |
| HUP9903885A2 (hu) | 2000-11-28 |
| SK46599A3 (en) | 2000-02-14 |
| CZ129299A3 (cs) | 1999-07-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU733967B2 (en) | Use of 1-benzyl-3-(substituted hetaryl)-fused pyrazole derivatives for the treatment of specific disorders of the cardiovascular system and of the central nervous system | |
| KR101011864B1 (ko) | 카르바메이트-치환된 피라졸로피리딘 | |
| US6833364B1 (en) | Substituted pyrazole derivatives | |
| JP6324956B2 (ja) | 置換アミノインダン−およびアミノテトラリンカルボン酸ならびにその使用 | |
| CN105814038B (zh) | 作为ep4配体的苯并咪唑衍生物 | |
| JP4589720B2 (ja) | ２−（１−ベンジル−１ｈ−ピラゾロ（３，４−ｂ）ピリジン−３−イル）−５−（４−ピリジニル）−４−ピリミジンアミン誘導体およびグアニル酸シクラーゼ刺激因子としてのそれらの使用 | |
| JP2004520285A (ja) | 新規なラクタム置換ピラゾロピリジン誘導体 | |
| RS53028B (sr) | Derivati pirazolo piridina kao inhibitori nadph oksidaze | |
| SK112395A3 (en) | Imidazopyridine derivative, preparation method thereof and pharmaceutical composition containing same | |
| JP2002540102A (ja) | ｃＧＭＰホスホジエステラーゼの縮合ピリドピリダジン阻害剤 | |
| OA10189A (en) | Use of indole derivatives as 5htl agonists | |
| EP1441724B1 (en) | Methods of increasing endogenous testosterone levels | |
| KR102473680B1 (ko) | 신규한 피라졸 유도체 | |
| WO2020177291A1 (zh) | 法舒地尔复合盐及其制备方法和用途 | |
| US20090005430A1 (en) | Receptor Blocker and Vasodilator Comprising Indole Derivative as Active Ingredient | |
| WO2020249117A1 (zh) | 抗高血压的多元醇化合物及其衍生物 | |
| TW200813007A (en) | Substituted pyrrole derivatives | |
| MXPA99003433A (en) | Use of condensated (hetaryl-substituted) 1-benzal-3-pyrazol derivates for treating special diseases of the cardiovascular and the central nervous systems | |
| CN1240354A (zh) | 1－苄基－3－取代杂芳基稠合吡唑衍生物用于治疗心血管系统和中枢神经系统特异性疾病的应用 | |
| HK1022646A (en) | Use of 1-benzyl-3-(substituted hetaryl)- fused pyrazole derivatives for treating special diseases of the cardiovascular and the central nervous systems | |
| TW379220B (en) | Pyrazolidine derivative, radical scavenger, brain--infarction depressant, and brain-edma depressant | |
| WO1991016311A1 (fr) | Derive d'acide 7-(hydrazino substitue)-4-oxoquinoline-3-carboxylique, son sel et son ester |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |