BG62768B1 - Пиридазинонови производни и методи за получаването им - Google Patents
Пиридазинонови производни и методи за получаването им Download PDFInfo
- Publication number
- BG62768B1 BG62768B1 BG100684A BG10068496A BG62768B1 BG 62768 B1 BG62768 B1 BG 62768B1 BG 100684 A BG100684 A BG 100684A BG 10068496 A BG10068496 A BG 10068496A BG 62768 B1 BG62768 B1 BG 62768B1
- Authority
- BG
- Bulgaria
- Prior art keywords
- group
- substituted
- atom
- pyridyl
- carbon atoms
- Prior art date
Links
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 238000002360 preparation method Methods 0.000 title claims description 22
- 238000000034 method Methods 0.000 title claims description 19
- -1 sulphonyl group Chemical group 0.000 claims abstract description 187
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 83
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 77
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 48
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 40
- 150000003839 salts Chemical class 0.000 claims abstract description 36
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 15
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims abstract description 7
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 154
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 72
- 125000001424 substituent group Chemical group 0.000 claims description 51
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 42
- 125000003277 amino group Chemical group 0.000 claims description 36
- 125000003545 alkoxy group Chemical group 0.000 claims description 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- 125000003282 alkyl amino group Chemical group 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 19
- 229910052717 sulfur Inorganic materials 0.000 claims description 19
- 125000004434 sulfur atom Chemical group 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 18
- 125000004076 pyridyl group Chemical group 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
- 125000005842 heteroatom Chemical group 0.000 claims description 13
- 125000002950 monocyclic group Chemical group 0.000 claims description 13
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 12
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 12
- 125000004414 alkyl thio group Chemical group 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 11
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
- 125000006323 alkenyl amino group Chemical group 0.000 claims description 7
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 6
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 6
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 125000004442 acylamino group Chemical group 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 3
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
- 125000005493 quinolyl group Chemical group 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- RCVLQLLCIGNCNJ-UHFFFAOYSA-N N1=CC(=CC=C1)C(=O)NCCCCC1=CC=C(C=C1)C1=CC=CN=N1 Chemical compound N1=CC(=CC=C1)C(=O)NCCCCC1=CC=C(C=C1)C1=CC=CN=N1 RCVLQLLCIGNCNJ-UHFFFAOYSA-N 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 abstract description 2
- 239000001301 oxygen Substances 0.000 abstract description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 229920002554 vinyl polymer Polymers 0.000 description 68
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 55
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 51
- 239000000203 mixture Substances 0.000 description 51
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 37
- 239000000243 solution Substances 0.000 description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- 239000002904 solvent Substances 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
- 239000013078 crystal Substances 0.000 description 25
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- 239000007858 starting material Substances 0.000 description 23
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 18
- 238000001914 filtration Methods 0.000 description 17
- 239000000725 suspension Substances 0.000 description 17
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 14
- 239000005457 ice water Substances 0.000 description 14
- 230000000704 physical effect Effects 0.000 description 14
- 238000001816 cooling Methods 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 11
- 230000036772 blood pressure Effects 0.000 description 11
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 10
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 9
- 102000004169 proteins and genes Human genes 0.000 description 9
- 108090000623 proteins and genes Proteins 0.000 description 9
- 125000004042 4-aminobutyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])N([H])[H] 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 7
- 125000002252 acyl group Chemical group 0.000 description 7
- 239000003480 eluent Substances 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 201000008383 nephritis Diseases 0.000 description 7
- 230000002861 ventricular Effects 0.000 description 7
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 6
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 241001631457 Cannula Species 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- 206010040070 Septic Shock Diseases 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 230000000747 cardiac effect Effects 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
- 229960003512 nicotinic acid Drugs 0.000 description 5
- 235000001968 nicotinic acid Nutrition 0.000 description 5
- 239000011664 nicotinic acid Substances 0.000 description 5
- 125000006239 protecting group Chemical group 0.000 description 5
- 230000035488 systolic blood pressure Effects 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- WZICYOARYXPFCD-UHFFFAOYSA-N 1h-pyridazin-6-one;hydrobromide Chemical compound Br.O=C1C=CC=NN1 WZICYOARYXPFCD-UHFFFAOYSA-N 0.000 description 4
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 4
- RBNITPVPQPJIPE-UHFFFAOYSA-N C1CC(=NN=C1)C2=CC3=C(CC(C3)CNS(=O)(=O)C4=CC=C(C=C4)Cl)C=C2 Chemical compound C1CC(=NN=C1)C2=CC3=C(CC(C3)CNS(=O)(=O)C4=CC=C(C=C4)Cl)C=C2 RBNITPVPQPJIPE-UHFFFAOYSA-N 0.000 description 4
- 206010014824 Endotoxic shock Diseases 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 125000002619 bicyclic group Chemical group 0.000 description 4
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 125000005544 phthalimido group Chemical group 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 4
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 230000033764 rhythmic process Effects 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 4
- 125000006017 1-propenyl group Chemical group 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- VHCSBTPOPKFYIU-UHFFFAOYSA-N 2-chloroethanesulfonyl chloride Chemical compound ClCCS(Cl)(=O)=O VHCSBTPOPKFYIU-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- ZHWPTBJQTJMPJA-UHFFFAOYSA-N n-(4-phenylbutyl)acetamide Chemical compound CC(=O)NCCCCC1=CC=CC=C1 ZHWPTBJQTJMPJA-UHFFFAOYSA-N 0.000 description 3
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 3
- 125000004193 piperazinyl group Chemical group 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- JEQDSBVHLKBEIZ-REOHCLBHSA-N (2s)-2-chloropropanoyl chloride Chemical compound C[C@H](Cl)C(Cl)=O JEQDSBVHLKBEIZ-REOHCLBHSA-N 0.000 description 2
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- NYLYQIYULMIBEX-UHFFFAOYSA-N 3-[4-(4-aminobutoxy)phenyl]-4,5-dihydro-1h-pyridazin-6-one Chemical compound C1=CC(OCCCCN)=CC=C1C1=NNC(=O)CC1 NYLYQIYULMIBEX-UHFFFAOYSA-N 0.000 description 2
- LVCNCVDHHGUFDG-UHFFFAOYSA-N 3-[4-(4-aminobutyl)phenyl]-1h-pyridazin-6-one Chemical compound C1=CC(CCCCN)=CC=C1C1=NNC(=O)C=C1 LVCNCVDHHGUFDG-UHFFFAOYSA-N 0.000 description 2
- JYNXPPLBHZEBBN-UHFFFAOYSA-N 3-[4-(4-aminobutyl)phenyl]-4,5-dihydro-1h-pyridazin-6-one Chemical compound C1=CC(CCCCN)=CC=C1C1=NNC(=O)CC1 JYNXPPLBHZEBBN-UHFFFAOYSA-N 0.000 description 2
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 2
- ORSUMIZRRGPJBR-UHFFFAOYSA-N 4,5-dihydro-1h-pyridazin-6-one Chemical compound O=C1CCC=NN1 ORSUMIZRRGPJBR-UHFFFAOYSA-N 0.000 description 2
- MGSDIYPQOAHHCH-UHFFFAOYSA-N 4-[4-[4-(1,3-dioxoisoindol-2-yl)butoxy]phenyl]-4-oxobutanoic acid Chemical compound C1=CC(C(=O)CCC(=O)O)=CC=C1OCCCCN1C(=O)C2=CC=CC=C2C1=O MGSDIYPQOAHHCH-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- DGYIJVNZSDYBOE-UHFFFAOYSA-N [CH2]C1=CC=NC=C1 Chemical group [CH2]C1=CC=NC=C1 DGYIJVNZSDYBOE-UHFFFAOYSA-N 0.000 description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 description 2
- 230000001518 anti-nephritic effect Effects 0.000 description 2
- 230000002785 anti-thrombosis Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 150000001718 carbodiimides Chemical class 0.000 description 2
- DCFKHNIGBAHNSS-UHFFFAOYSA-N chloro(triethyl)silane Chemical compound CC[Si](Cl)(CC)CC DCFKHNIGBAHNSS-UHFFFAOYSA-N 0.000 description 2
- MCXRBTCDEDZSMV-UHFFFAOYSA-N diethylphosphanylformonitrile Chemical compound CCP(CC)C#N MCXRBTCDEDZSMV-UHFFFAOYSA-N 0.000 description 2
- CLPHAYNBNTVRDI-UHFFFAOYSA-N ditert-butyl propanedioate Chemical compound CC(C)(C)OC(=O)CC(=O)OC(C)(C)C CLPHAYNBNTVRDI-UHFFFAOYSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 230000029142 excretion Effects 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
- MSYBLBLAMDYKKZ-UHFFFAOYSA-N hydron;pyridine-3-carbonyl chloride;chloride Chemical compound Cl.ClC(=O)C1=CC=CN=C1 MSYBLBLAMDYKKZ-UHFFFAOYSA-N 0.000 description 2
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 2
- 210000005240 left ventricle Anatomy 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- NHLHADYTCXGRTG-UHFFFAOYSA-N methyl 4-[4-(6-acetamidohexyl)phenyl]-4-oxobutanoate Chemical compound COC(=O)CCC(=O)C1=CC=C(CCCCCCNC(C)=O)C=C1 NHLHADYTCXGRTG-UHFFFAOYSA-N 0.000 description 2
- IQXSFOQVUYGRQB-UHFFFAOYSA-N n-[2-[4-(4-methyl-6-oxo-4,5-dihydro-1h-pyridazin-3-yl)phenyl]ethyl]pyridine-3-carboxamide Chemical compound CC1CC(=O)NN=C1C(C=C1)=CC=C1CCNC(=O)C1=CC=CN=C1 IQXSFOQVUYGRQB-UHFFFAOYSA-N 0.000 description 2
- FVBOLUWYYRQDGW-UHFFFAOYSA-N n-[3-[4-(6-oxo-1h-pyridazin-3-yl)phenyl]propyl]ethenesulfonamide Chemical compound C1=CC(CCCNS(=O)(=O)C=C)=CC=C1C1=NNC(=O)C=C1 FVBOLUWYYRQDGW-UHFFFAOYSA-N 0.000 description 2
- FSFDYZQVBJLNDE-UHFFFAOYSA-N n-[4-[4-(2-chloropropanoyl)phenyl]butyl]acetamide Chemical compound CC(Cl)C(=O)C1=CC=C(CCCCNC(C)=O)C=C1 FSFDYZQVBJLNDE-UHFFFAOYSA-N 0.000 description 2
- NANKFGYKYUNOMK-UHFFFAOYSA-N n-[4-[4-(3-cyanobutanoyl)phenyl]butyl]acetamide Chemical compound N#CC(C)CC(=O)C1=CC=C(CCCCNC(C)=O)C=C1 NANKFGYKYUNOMK-UHFFFAOYSA-N 0.000 description 2
- XCYVPMATTGSFTD-UHFFFAOYSA-N n-[4-[4-(6-oxo-1h-pyridazin-3-yl)phenyl]butyl]pyridine-3-carboxamide Chemical compound C=1C=CN=CC=1C(=O)NCCCCC(C=C1)=CC=C1C=1C=CC(=O)NN=1 XCYVPMATTGSFTD-UHFFFAOYSA-N 0.000 description 2
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 2
- 229960001412 pentobarbital Drugs 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004941 pyridazin-5-yl group Chemical group N1=NC=CC(=C1)* 0.000 description 2
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 2
- 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 2
- 150000003254 radicals Chemical class 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 229940014800 succinic anhydride Drugs 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- 125000003831 tetrazolyl group Chemical group 0.000 description 2
- RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical group C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 description 2
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 2
- 239000005051 trimethylchlorosilane Substances 0.000 description 2
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- 210000002700 urine Anatomy 0.000 description 2
- 238000011706 wistar kyoto rat Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- FTTATHOUSOIFOQ-UHFFFAOYSA-N 1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine Chemical compound C1NCCN2CCCC21 FTTATHOUSOIFOQ-UHFFFAOYSA-N 0.000 description 1
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 1
- 125000006039 1-hexenyl group Chemical group 0.000 description 1
- JNLBRMDGJDSLLQ-UHFFFAOYSA-N 1h-pyridazin-6-one;hydrochloride Chemical compound Cl.O=C1C=CC=NN1 JNLBRMDGJDSLLQ-UHFFFAOYSA-N 0.000 description 1
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
- IDTXXTLDITWTDQ-UHFFFAOYSA-N 2-(3-phenoxypropyl)isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCCOC1=CC=CC=C1 IDTXXTLDITWTDQ-UHFFFAOYSA-N 0.000 description 1
- JSTJUWALPZLQDJ-UHFFFAOYSA-N 2-[3-[4-(2-chloropropanoyl)phenoxy]propyl]isoindole-1,3-dione Chemical compound C1=CC(C(=O)C(Cl)C)=CC=C1OCCCN1C(=O)C2=CC=CC=C2C1=O JSTJUWALPZLQDJ-UHFFFAOYSA-N 0.000 description 1
- WXHLLJAMBQLULT-UHFFFAOYSA-N 2-[[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-yl]amino]-n-(2-methyl-6-sulfanylphenyl)-1,3-thiazole-5-carboxamide;hydrate Chemical compound O.C=1C(N2CCN(CCO)CC2)=NC(C)=NC=1NC(S1)=NC=C1C(=O)NC1=C(C)C=CC=C1S WXHLLJAMBQLULT-UHFFFAOYSA-N 0.000 description 1
- KPIVDNYJNOPGBE-UHFFFAOYSA-N 2-aminonicotinic acid Chemical compound NC1=NC=CC=C1C(O)=O KPIVDNYJNOPGBE-UHFFFAOYSA-N 0.000 description 1
- 125000006040 2-hexenyl group Chemical group 0.000 description 1
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 1
- LDJBXUARDDEMAM-UHFFFAOYSA-N 2-methylsulfinyl-n-[3-[4-(6-oxo-1h-pyridazin-3-yl)phenyl]propyl]ethanesulfonamide Chemical compound C1=CC(CCCNS(=O)(=O)CCS(=O)C)=CC=C1C1=NNC(=O)C=C1 LDJBXUARDDEMAM-UHFFFAOYSA-N 0.000 description 1
- 125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 description 1
- GKECDORWWXXNRY-UHFFFAOYSA-N 2h-pyridin-3-one Chemical compound O=C1CN=CC=C1 GKECDORWWXXNRY-UHFFFAOYSA-N 0.000 description 1
- VZGYFECTMUPKDN-UHFFFAOYSA-N 3-[2-(4-aminobutyl)-5-chlorophenyl]-4,5-dihydro-1h-pyridazin-6-one Chemical compound NCCCCC1=CC=C(Cl)C=C1C1=NNC(=O)CC1 VZGYFECTMUPKDN-UHFFFAOYSA-N 0.000 description 1
- YAIRUQLRYQATKY-UHFFFAOYSA-N 3-[3-(4-aminobutyl)phenyl]-4,5-dihydro-1h-pyridazin-6-one Chemical compound NCCCCC1=CC=CC(C=2CCC(=O)NN=2)=C1 YAIRUQLRYQATKY-UHFFFAOYSA-N 0.000 description 1
- OPJBEQFIGXOOHH-UHFFFAOYSA-N 3-[4-(3-aminopropoxy)phenyl]-1h-pyridazin-6-one;hydrobromide Chemical compound Br.C1=CC(OCCCN)=CC=C1C1=NNC(=O)C=C1 OPJBEQFIGXOOHH-UHFFFAOYSA-N 0.000 description 1
- SCIPBIGXCHSMMG-UHFFFAOYSA-N 3-[4-(3-aminopropyl)phenyl]-1h-pyridazin-6-one;hydrobromide Chemical compound Br.C1=CC(CCCN)=CC=C1C1=NNC(=O)C=C1 SCIPBIGXCHSMMG-UHFFFAOYSA-N 0.000 description 1
- JELXJGGUVHVTCV-UHFFFAOYSA-N 3-[4-(3-aminopropyl)phenyl]-4,5-dihydro-1h-pyridazin-6-one Chemical compound C1=CC(CCCN)=CC=C1C1=NNC(=O)CC1 JELXJGGUVHVTCV-UHFFFAOYSA-N 0.000 description 1
- PIBCJAWQVWYJHI-UHFFFAOYSA-N 3-[4-(4-aminobutyl)-3-methylphenyl]-4,5-dihydro-1h-pyridazin-6-one Chemical compound C1=C(CCCCN)C(C)=CC(C=2CCC(=O)NN=2)=C1 PIBCJAWQVWYJHI-UHFFFAOYSA-N 0.000 description 1
- ZBZZGVFGFIUYPD-UHFFFAOYSA-N 3-[4-(4-aminobutyl)phenyl]-1h-pyridazin-6-one;hydrobromide Chemical compound Br.C1=CC(CCCCN)=CC=C1C1=NNC(=O)C=C1 ZBZZGVFGFIUYPD-UHFFFAOYSA-N 0.000 description 1
- SAJXRTRZPBVMSL-UHFFFAOYSA-N 3-[4-(4-aminobutyl)phenyl]-4,5-dimethyl-1h-pyridazin-6-one Chemical compound CC1=C(C)C(=O)NN=C1C1=CC=C(CCCCN)C=C1 SAJXRTRZPBVMSL-UHFFFAOYSA-N 0.000 description 1
- UJBHWUYIJYXDIS-UHFFFAOYSA-N 3-[4-(6-aminohexyl)phenyl]-4,5-dihydro-1h-pyridazin-6-one Chemical compound C1=CC(CCCCCCN)=CC=C1C1=NNC(=O)CC1 UJBHWUYIJYXDIS-UHFFFAOYSA-N 0.000 description 1
- MNBWIQZDIBGKHO-UHFFFAOYSA-N 3-[5-(4-aminobutyl)-2-chlorophenyl]-4,5-dihydro-1h-pyridazin-6-one Chemical compound NCCCCC1=CC=C(Cl)C(C=2CCC(=O)NN=2)=C1 MNBWIQZDIBGKHO-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000006041 3-hexenyl group Chemical group 0.000 description 1
- HXIYCKAAQPHZBM-UHFFFAOYSA-N 3-methyl-1,2-oxazole-5-carboxylic acid Chemical compound CC=1C=C(C(O)=O)ON=1 HXIYCKAAQPHZBM-UHFFFAOYSA-N 0.000 description 1
- XWNSDZPPORLJQQ-UHFFFAOYSA-N 4-[4-[4-(1,3-dioxoisoindol-2-yl)-2-methylbutyl]phenyl]-4-oxobutanoic acid Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCC(C)CC1=CC=C(C(=O)CCC(O)=O)C=C1 XWNSDZPPORLJQQ-UHFFFAOYSA-N 0.000 description 1
- 125000006042 4-hexenyl group Chemical group 0.000 description 1
- KMQLIDDEQAJAGJ-UHFFFAOYSA-N 4-oxo-4-phenylbutyric acid Chemical compound OC(=O)CCC(=O)C1=CC=CC=C1 KMQLIDDEQAJAGJ-UHFFFAOYSA-N 0.000 description 1
- 125000006043 5-hexenyl group Chemical group 0.000 description 1
- AHWLNKORVXQHFB-UHFFFAOYSA-N 5-methyl-4,5-dihydro-1h-pyridazin-6-one Chemical compound CC1CC=NNC1=O AHWLNKORVXQHFB-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 108010039627 Aprotinin Proteins 0.000 description 1
- VWOYBQLIVMVVPX-UHFFFAOYSA-N C1=CC=NC(=C1)C2=CC=C(C=C2)OCCCCNC(=O)C3=CN=CC=C3 Chemical compound C1=CC=NC(=C1)C2=CC=C(C=C2)OCCCCNC(=O)C3=CN=CC=C3 VWOYBQLIVMVVPX-UHFFFAOYSA-N 0.000 description 1
- UYAHDRZYVURLTL-UHFFFAOYSA-N C1CC(=NN=C1)C2=CC=C(C=C2)CCCCN Chemical compound C1CC(=NN=C1)C2=CC=C(C=C2)CCCCN UYAHDRZYVURLTL-UHFFFAOYSA-N 0.000 description 1
- FXMKUPGYFLZXEB-UHFFFAOYSA-N CC(=O)NCCCCC1=CC=C(C=C1)CCCC(=O)OC Chemical compound CC(=O)NCCCCC1=CC=C(C=C1)CCCC(=O)OC FXMKUPGYFLZXEB-UHFFFAOYSA-N 0.000 description 1
- ZRVKYKMYXRZJHN-UHFFFAOYSA-N CC1=C(C=CC(=C1)C2=NN=CCC2)CCCCN Chemical compound CC1=C(C=CC(=C1)C2=NN=CCC2)CCCCN ZRVKYKMYXRZJHN-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- JRWZLRBJNMZMFE-UHFFFAOYSA-N Dobutamine Chemical compound C=1C=C(O)C(O)=CC=1CCNC(C)CCC1=CC=C(O)C=C1 JRWZLRBJNMZMFE-UHFFFAOYSA-N 0.000 description 1
- 239000001116 FEMA 4028 Substances 0.000 description 1
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 1
- 208000010159 IgA glomerulonephritis Diseases 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- NEXRPJQHVOSBSI-UHFFFAOYSA-N N-[5-[4-(6-oxo-1H-pyridazin-3-yl)phenyl]pentyl]pyridine-3-carboxamide Chemical compound C=1C=CN=CC=1C(=O)NCCCCCC(C=C1)=CC=C1C=1C=CC(=O)NN=1 NEXRPJQHVOSBSI-UHFFFAOYSA-N 0.000 description 1
- 206010065673 Nephritic syndrome Diseases 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229940124158 Protease/peptidase inhibitor Drugs 0.000 description 1
- 208000001647 Renal Insufficiency Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- ONXFNBOZJKXCNC-ZJSXRUAMSA-N [(3aR,9bR)-9b-(4-fluorophenyl)sulfonyl-7-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2,3a,4,5-tetrahydro-1H-benzo[e]indol-3-yl]-(4-hydroxy-1,1-dioxothian-4-yl)methanone Chemical compound OC1(CCS(=O)(=O)CC1)C(=O)N1CC[C@@]2([C@H]1CCc1cc(ccc21)C(F)(C(F)(F)F)C(F)(F)F)S(=O)(=O)c1ccc(F)cc1 ONXFNBOZJKXCNC-ZJSXRUAMSA-N 0.000 description 1
- 230000003187 abdominal effect Effects 0.000 description 1
- BVVCDLLKIBUISQ-UHFFFAOYSA-N acetonitrile;pyridine Chemical compound CC#N.C1=CC=NC=C1 BVVCDLLKIBUISQ-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000005819 alkenylalkoxy group Chemical group 0.000 description 1
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 239000002269 analeptic agent Substances 0.000 description 1
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 229940127219 anticoagulant drug Drugs 0.000 description 1
- 229960004405 aprotinin Drugs 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 229960004853 betadex Drugs 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
- 210000001168 carotid artery common Anatomy 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229960004397 cyclophosphamide Drugs 0.000 description 1
- 230000002354 daily effect Effects 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 231100000517 death Toxicity 0.000 description 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- IZEKFCXSFNUWAM-UHFFFAOYSA-N dipyridamole Chemical compound C=12N=C(N(CCO)CCO)N=C(N3CCCCC3)C2=NC(N(CCO)CCO)=NC=1N1CCCCC1 IZEKFCXSFNUWAM-UHFFFAOYSA-N 0.000 description 1
- 229960002768 dipyridamole Drugs 0.000 description 1
- 229960001089 dobutamine Drugs 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 210000001105 femoral artery Anatomy 0.000 description 1
- 210000003191 femoral vein Anatomy 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000001434 glomerular Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229960002897 heparin Drugs 0.000 description 1
- 229920000669 heparin Polymers 0.000 description 1
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005935 hexyloxycarbonyl group Chemical group 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229960003444 immunosuppressant agent Drugs 0.000 description 1
- 230000001861 immunosuppressant effect Effects 0.000 description 1
- 239000003018 immunosuppressive agent Substances 0.000 description 1
- ZPNFWUPYTFPOJU-LPYSRVMUSA-N iniprol Chemical compound C([C@H]1C(=O)NCC(=O)NCC(=O)N[C@H]2CSSC[C@H]3C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@H](C(N[C@H](C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=4C=CC(O)=CC=4)C(=O)N[C@@H](CC=4C=CC=CC=4)C(=O)N[C@@H](CC=4C=CC(O)=CC=4)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC=4C=CC=CC=4)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC2=O)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](CC=2C=CC=CC=2)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H]2N(CCC2)C(=O)[C@@H](N)CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N2[C@@H](CCC2)C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N2[C@@H](CCC2)C(=O)N3)C(=O)NCC(=O)NCC(=O)N[C@@H](C)C(O)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@H](C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@H](C(=O)N1)C(C)C)[C@@H](C)O)[C@@H](C)CC)=O)[C@@H](C)CC)C1=CC=C(O)C=C1 ZPNFWUPYTFPOJU-LPYSRVMUSA-N 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000005921 isopentoxy group Chemical group 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 201000006370 kidney failure Diseases 0.000 description 1
- WOFDVDFSGLBFAC-UHFFFAOYSA-N lactonitrile Chemical compound CC(O)C#N WOFDVDFSGLBFAC-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- YCKDYKJGWQCSSZ-UHFFFAOYSA-N methyl 4-[4-(4-acetamidobutyl)phenyl]-4-oxobutanoate Chemical compound COC(=O)CCC(=O)C1=CC=C(CCCCNC(C)=O)C=C1 YCKDYKJGWQCSSZ-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- UPDMJJCVOSZTPB-UHFFFAOYSA-N n-[2-[4-(6-oxo-1h-pyridazin-3-yl)phenyl]ethyl]benzenesulfonamide Chemical compound N1C(=O)C=CC(C=2C=CC(CCNS(=O)(=O)C=3C=CC=CC=3)=CC=2)=N1 UPDMJJCVOSZTPB-UHFFFAOYSA-N 0.000 description 1
- PQFMYGKNZOVJTI-UHFFFAOYSA-N n-[3-[4-(6-oxo-1h-pyridazin-3-yl)phenoxy]propyl]ethenesulfonamide Chemical compound C1=CC(OCCCNS(=O)(=O)C=C)=CC=C1C1=NNC(=O)C=C1 PQFMYGKNZOVJTI-UHFFFAOYSA-N 0.000 description 1
- LHRJOFADACZEJQ-UHFFFAOYSA-N n-[4-(4-but-2-enoylphenyl)butyl]acetamide Chemical compound CC=CC(=O)C1=CC=C(CCCCNC(C)=O)C=C1 LHRJOFADACZEJQ-UHFFFAOYSA-N 0.000 description 1
- BPOARDYCVMTCPG-UHFFFAOYSA-N n-[4-[2-methyl-4-(6-oxo-4,5-dihydro-1h-pyridazin-3-yl)phenyl]butyl]pyridine-3-carboxamide Chemical compound CC1=CC(C=2CCC(=O)NN=2)=CC=C1CCCCNC(=O)C1=CC=CN=C1 BPOARDYCVMTCPG-UHFFFAOYSA-N 0.000 description 1
- IXYNFTBKOWLYFP-UHFFFAOYSA-N n-[4-[4-(6-oxo-1h-pyridazin-3-yl)phenyl]butyl]pyridazine-4-carboxamide Chemical compound C=1C=NN=CC=1C(=O)NCCCCC(C=C1)=CC=C1C=1C=CC(=O)NN=1 IXYNFTBKOWLYFP-UHFFFAOYSA-N 0.000 description 1
- YTVJWXUDWOGKMO-UHFFFAOYSA-N n-[4-[4-(6-oxo-1h-pyridazin-3-yl)phenyl]butyl]pyridine-3-carboxamide;hydrochloride Chemical compound Cl.C=1C=CN=CC=1C(=O)NCCCCC(C=C1)=CC=C1C=1C=CC(=O)NN=1 YTVJWXUDWOGKMO-UHFFFAOYSA-N 0.000 description 1
- QZBKVTCSHKEHNY-UHFFFAOYSA-N n-[4-[4-(6-oxo-4,5-dihydro-1h-pyridazin-3-yl)phenyl]butyl]pyridine-3-carboxamide Chemical compound C=1C=CN=CC=1C(=O)NCCCCC(C=C1)=CC=C1C1=NNC(=O)CC1 QZBKVTCSHKEHNY-UHFFFAOYSA-N 0.000 description 1
- YNTABQARIZLXGJ-UHFFFAOYSA-N n-[5-[4-(6-oxo-4,5-dihydro-1h-pyridazin-3-yl)phenyl]pentyl]pyridine-3-carboxamide Chemical compound C=1C=CN=CC=1C(=O)NCCCCCC(C=C1)=CC=C1C1=NNC(=O)CC1 YNTABQARIZLXGJ-UHFFFAOYSA-N 0.000 description 1
- YZVFFEHBWCNAFP-UHFFFAOYSA-N n-[6-[4-(6-oxo-1h-pyridazin-3-yl)phenyl]hexyl]pyridine-3-carboxamide Chemical compound C=1C=CN=CC=1C(=O)NCCCCCCC(C=C1)=CC=C1C=1C=CC(=O)NN=1 YZVFFEHBWCNAFP-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000003589 nefrotoxic effect Effects 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 231100000381 nephrotoxic Toxicity 0.000 description 1
- KPADFPAILITQBG-UHFFFAOYSA-N non-4-ene Chemical compound CCCCC=CCCC KPADFPAILITQBG-UHFFFAOYSA-N 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
- 239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
- 230000004526 pharmaceutical effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 1
- 229960005205 prednisolone Drugs 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- JUSIWJONLKBPDU-UHFFFAOYSA-N pyridazine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NN=C1 JUSIWJONLKBPDU-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- 238000005932 reductive alkylation reaction Methods 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
- LJRGBERXYNQPJI-UHFFFAOYSA-M sodium;3-nitrobenzenesulfonate Chemical compound [Na+].[O-][N+](=O)C1=CC=CC(S([O-])(=O)=O)=C1 LJRGBERXYNQPJI-UHFFFAOYSA-M 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000011272 standard treatment Methods 0.000 description 1
- 239000003270 steroid hormone Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- RUPAXCPQAAOIPB-UHFFFAOYSA-N tert-butyl formate Chemical group CC(C)(C)OC=O RUPAXCPQAAOIPB-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane Chemical compound CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/14—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Urology & Nephrology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Optical Couplings Of Light Guides (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16062095 | 1995-06-27 | ||
| JP1985996 | 1996-02-06 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BG100684A BG100684A (bg) | 1997-03-31 |
| BG62768B1 true BG62768B1 (bg) | 2000-07-31 |
Family
ID=26356726
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG100684A BG62768B1 (bg) | 1995-06-27 | 1996-06-27 | Пиридазинонови производни и методи за получаването им |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US5698554A (de) |
| EP (1) | EP0751132B1 (de) |
| KR (1) | KR970061873A (de) |
| CN (1) | CN1144802A (de) |
| AR (1) | AR002602A1 (de) |
| AT (1) | ATE195937T1 (de) |
| AU (1) | AU694955B2 (de) |
| BG (1) | BG62768B1 (de) |
| CA (1) | CA2179939A1 (de) |
| DE (1) | DE69610036T2 (de) |
| DK (1) | DK0751132T3 (de) |
| ES (1) | ES2151110T3 (de) |
| GR (1) | GR3034910T3 (de) |
| HU (1) | HUP9601766A3 (de) |
| IL (1) | IL118631A (de) |
| MY (1) | MY132263A (de) |
| NO (1) | NO311084B1 (de) |
| PT (1) | PT751132E (de) |
| RU (1) | RU2131419C1 (de) |
| SG (1) | SG46741A1 (de) |
| TW (1) | TW432052B (de) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2424551A1 (en) * | 1997-05-27 | 1998-11-27 | Schneider (Usa) Inc. | Stent and stent-graft for treating branched vessels |
| CO5200835A1 (es) * | 1999-09-28 | 2002-09-27 | Bayer Corp | Piridinas y piridacinas sustituidas con actividad de inhibicion de angiogenesis |
| KR20030061051A (ko) * | 2002-01-07 | 2003-07-18 | 대한민국 (경상대학교 총장) | 신규한 아렌(혹은 알케인)술폰일피리다진온 유도체, 이의제조방법 및 유기반응에서의 용도 |
| AR050552A1 (es) * | 2004-09-02 | 2006-11-01 | Osi Pharm Inc | Mercaptoamidas como inhibidores de histona desacetilasa |
| CN101443317B (zh) * | 2006-03-17 | 2011-07-06 | 住友化学株式会社 | 哒嗪酮化合物及其作为除草剂的用途 |
| MX2009000884A (es) * | 2006-07-25 | 2009-06-05 | Cephalon Inc | Derivados de piridizinona. |
| WO2009063244A1 (en) * | 2007-11-15 | 2009-05-22 | Istituto Di Ricerche Di Biologia Molecolare P. Angeletti S.P.A. | Pyridazinone derivatives as parp inhibitors |
| EP2547203A4 (de) * | 2010-03-19 | 2013-12-25 | Purdue Research Foundation | Ccr5-modulatoren zur hiv-behandlung |
| PH12013500907A1 (en) | 2010-11-05 | 2013-07-08 | Firmenich Incorporated | Compounds useful as modulators of trpm8 |
| MY157429A (en) | 2011-06-24 | 2016-06-15 | Amgen Inc | Trpm8 antagonists and their use in treatments |
| JP2014517074A (ja) | 2011-06-24 | 2014-07-17 | アムジエン・インコーポレーテツド | Ｔｒｐｍ８アンタゴニストおよび治療におけるそれらの使用 |
| WO2013097052A1 (en) | 2011-12-30 | 2013-07-04 | Abbott Laboratories | Bromodomain inhibitors |
| US8952009B2 (en) | 2012-08-06 | 2015-02-10 | Amgen Inc. | Chroman derivatives as TRPM8 inhibitors |
| EP3356356B1 (de) | 2015-10-01 | 2021-05-26 | Firmenich Incorporated | Verbindungen als trpm8-modulatoren |
| ES2793239T3 (es) | 2016-04-15 | 2020-11-13 | Abbvie Inc | Inhibidores del bromodominio |
| AU2019372121A1 (en) * | 2018-10-30 | 2021-05-27 | Nuvation Bio Inc. | Heterocyclic compounds as BET inhibitors |
| AU2019374812B2 (en) | 2018-11-06 | 2025-03-06 | Edgewise Therapeutics, Inc. | Pyridazinone compounds and uses thereof |
| KR102885525B1 (ko) | 2018-11-06 | 2025-11-13 | 엣지와이즈 테라퓨틱스, 인크. | 피리다지논 화합물 및 이의 용도 |
| BR112021008905A2 (pt) | 2018-11-06 | 2021-08-10 | Edgewise Therapeutics, Inc. | compostos de piridazinona e usos dos mesmos |
| AU2020299592A1 (en) | 2019-07-02 | 2022-02-17 | Nuvation Bio Inc. | Heterocyclic compounds as BET inhibitors |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6053022B2 (ja) | 1977-04-07 | 1985-11-22 | ウェルファイド株式会社 | ピリダジノン誘導体 |
| GB8323553D0 (en) * | 1983-09-02 | 1983-10-05 | Smith Kline French Lab | Pharmaceutical compositions |
| JPS6193169A (ja) * | 1984-10-12 | 1986-05-12 | Sankyo Co Ltd | ピリダジノン誘導体及びその製法 |
| KR860007219A (ko) * | 1985-03-12 | 1986-10-08 | 베쩰, 좀머 | 설포닐아미노에틸 화합물의 제조방법 |
| EP0194548A3 (de) * | 1985-03-12 | 1988-08-17 | Dr. Karl Thomae GmbH | Neue Sulfonylaminoäthylverbindungen, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
| DE3508692A1 (de) | 1985-03-12 | 1986-09-18 | Dr. Karl Thomae Gmbh, 7950 Biberach | 3-(4-(2-benzolsulfonylamino-aethyl)-benzoyl)propionsaeure, diese verbindung enthaltende arzneimittel und verfahren zu ihrer herstellung |
| DE3623944A1 (de) * | 1986-07-16 | 1988-02-11 | Thomae Gmbh Dr K | Neue benzolsulfonamido-indanylverbindungen, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| JPS63145272A (ja) * | 1986-12-09 | 1988-06-17 | Morishita Seiyaku Kk | ４，５−ジヒドロ−６−（４−置換フエニル）−３（２ｈ）−ピリダジノン誘導体 |
| SU1486061A3 (ru) * | 1987-03-26 | 1989-06-07 | Mitsubishi Chem Ind | Способ получения производных пиридазинона или их солей |
| DE3728491A1 (de) * | 1987-08-26 | 1989-03-09 | Heumann Pharma Gmbh & Co | Dihydropyridazinon-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DE4134467A1 (de) * | 1991-10-18 | 1993-04-22 | Thomae Gmbh Dr K | Heterobiarylderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| WO1992015558A1 (fr) | 1991-03-01 | 1992-09-17 | Zeria Pharmaceutical Co., Ltd. | Derive d'indane et antagoniste de thromboxane le contenant |
| CA2099743A1 (en) * | 1992-07-02 | 1994-01-03 | Akihiko Ishida | Pyridazinone derivatives and processes for preparing the same |
| JP2616584B2 (ja) * | 1992-07-02 | 1997-06-04 | 田辺製薬株式会社 | ピリダジノン誘導体及びその製法 |
| JP2757353B2 (ja) * | 1993-12-28 | 1998-05-25 | 田辺製薬株式会社 | インダン誘導体、その製法及びその合成中間体 |
| CA2138812A1 (en) * | 1993-12-28 | 1995-06-29 | Akihiko Ishida | Indane derivative and processes for preparing the same |
| CA2139088A1 (en) * | 1993-12-28 | 1995-06-29 | Akihiko Ishida | Indane derivatives, processes for preparing the same and synthetic intermediate of the same |
-
1996
- 1996-06-01 IL IL11863196A patent/IL118631A/en not_active IP Right Cessation
- 1996-06-21 NO NO19962643A patent/NO311084B1/no unknown
- 1996-06-26 AR AR10332096A patent/AR002602A1/es unknown
- 1996-06-26 TW TW085107678A patent/TW432052B/zh not_active IP Right Cessation
- 1996-06-26 MY MYPI96002583A patent/MY132263A/en unknown
- 1996-06-26 SG SG1996010164A patent/SG46741A1/en unknown
- 1996-06-26 RU RU96112778/04A patent/RU2131419C1/ru not_active IP Right Cessation
- 1996-06-26 HU HU9601766A patent/HUP9601766A3/hu unknown
- 1996-06-26 CA CA002179939A patent/CA2179939A1/en not_active Abandoned
- 1996-06-27 EP EP96110412A patent/EP0751132B1/de not_active Expired - Lifetime
- 1996-06-27 AU AU56221/96A patent/AU694955B2/en not_active Ceased
- 1996-06-27 DE DE69610036T patent/DE69610036T2/de not_active Expired - Fee Related
- 1996-06-27 BG BG100684A patent/BG62768B1/bg unknown
- 1996-06-27 DK DK96110412T patent/DK0751132T3/da active
- 1996-06-27 PT PT96110412T patent/PT751132E/pt unknown
- 1996-06-27 CN CN96106873A patent/CN1144802A/zh active Pending
- 1996-06-27 ES ES96110412T patent/ES2151110T3/es not_active Expired - Lifetime
- 1996-06-27 US US08/671,485 patent/US5698554A/en not_active Expired - Fee Related
- 1996-06-27 AT AT96110412T patent/ATE195937T1/de not_active IP Right Cessation
- 1996-06-27 KR KR1019960024718A patent/KR970061873A/ko not_active Ceased
-
1997
- 1997-08-25 US US08/917,113 patent/US5808065A/en not_active Expired - Fee Related
-
2000
- 2000-11-24 GR GR20000402616T patent/GR3034910T3/el not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0751132B1 (de) | 2000-08-30 |
| ATE195937T1 (de) | 2000-09-15 |
| HUP9601766A2 (en) | 1997-02-28 |
| DE69610036T2 (de) | 2001-04-12 |
| NO311084B1 (no) | 2001-10-08 |
| US5808065A (en) | 1998-09-15 |
| MY132263A (en) | 2007-09-28 |
| DK0751132T3 (da) | 2000-11-13 |
| DE69610036D1 (de) | 2000-10-05 |
| HUP9601766A3 (en) | 1998-04-28 |
| GR3034910T3 (en) | 2001-02-28 |
| SG46741A1 (en) | 1998-02-20 |
| HU9601766D0 (en) | 1996-08-28 |
| RU2131419C1 (ru) | 1999-06-10 |
| NO962643D0 (no) | 1996-06-21 |
| IL118631A0 (en) | 1996-10-16 |
| TW432052B (en) | 2001-05-01 |
| BG100684A (bg) | 1997-03-31 |
| NO962643L (no) | 1996-12-30 |
| AR002602A1 (es) | 1998-03-25 |
| PT751132E (pt) | 2000-12-29 |
| US5698554A (en) | 1997-12-16 |
| AU694955B2 (en) | 1998-08-06 |
| CA2179939A1 (en) | 1996-12-28 |
| AU5622196A (en) | 1997-01-09 |
| EP0751132A1 (de) | 1997-01-02 |
| KR970061873A (ko) | 1997-09-12 |
| ES2151110T3 (es) | 2000-12-16 |
| IL118631A (en) | 2002-05-23 |
| CN1144802A (zh) | 1997-03-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| BG100684A (bg) | Пиридазинонови производни и методи за получаването им | |
| RU2277094C2 (ru) | Производные n-гетероциклических соединений, фармацевтическая композиция на их основе и способ лечения | |
| TWI415845B (zh) | 用於治療與５-ｈｔ2ａ血清素受體相關聯病症之作為５-ｈｔ2ａ血清素受體之調節劑的吡唑衍生物 | |
| KR880001623B1 (ko) | 치환된 4, 5-디하이드로-6-(치환) 페닐-3(2h)-피리다지논류 및 6-(치환)페닐-3(2h)-피리다지논류 | |
| RU2293733C2 (ru) | Новые 1,2,4-триазольные соединения, способы их получения и содержащие их лекарственные средства | |
| JPWO1994014769A1 (ja) | Ｎ−置換インドール誘導体 | |
| AU683460B2 (en) | Propenoic acid derivatives | |
| CA2865714A1 (en) | Pyrazol-1-yl benzene sulfonamides as ccr9 antagonists | |
| CZ9697A3 (en) | Use of heterocyclic compound as dopamine-d3 ligands | |
| US4954501A (en) | Piperazine substituted 6-phenyldihydro-3(2H)-pyridazinones, and pharmaceutical preparations containing these | |
| JPS6363661A (ja) | ジヒドロピリジン抗アレルギ−および抗炎症剤 | |
| NZ207914A (en) | Indeno-pyridazinones and pharmaceutical compositions | |
| PL151696B1 (en) | Method of obtaining derivatives of quinolone | |
| US5543409A (en) | Indane derivatives for treating endotoxin shock and/or nephritis | |
| JP2002053577A (ja) | 新規ｎ−トリアゾリルメチル−ピペラジン誘導体、その製造方法および中間生成物、および前記誘導体を含有する医薬品 | |
| US4661484A (en) | Pyridazinone derivatives and salts thereof as cardiac stimulants | |
| CN107033149B (zh) | 一种dpp-4酶抑制剂及其制备和应用 | |
| EP0145019B1 (de) | Pyridazinon-Derivate und deren Salze | |
| ES2417488T3 (es) | Compuestos de triazol adecuados para tratar trastornos que responden a la modulación del receptor de dopamina D3 | |
| JP2969618B2 (ja) | ピリダジノン誘導体及びその製法 | |
| WO1994014769A1 (fr) | Derive indolique a substitution n | |
| EP0661273B1 (de) | Indan Derivate und Verfahren zu deren Herstellung | |
| JP3060454B2 (ja) | 医薬組成物 | |
| US5232922A (en) | Imidazole compounds, processes for their preparation, pharmaceuticals based on these compounds and some intermediates | |
| US4971968A (en) | Pyridazinone derivatives and salts thereof |