NO311084B1 - Pyridazinonforbindelse - Google Patents
Pyridazinonforbindelse Download PDFInfo
- Publication number
- NO311084B1 NO311084B1 NO19962643A NO962643A NO311084B1 NO 311084 B1 NO311084 B1 NO 311084B1 NO 19962643 A NO19962643 A NO 19962643A NO 962643 A NO962643 A NO 962643A NO 311084 B1 NO311084 B1 NO 311084B1
- Authority
- NO
- Norway
- Prior art keywords
- group
- hydrogen atom
- compound
- phenyl
- compound according
- Prior art date
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- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims description 117
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 33
- 150000003839 salts Chemical class 0.000 claims description 30
- -1 Pyridazinone compound Chemical class 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- 125000003277 amino group Chemical group 0.000 claims description 19
- 125000003342 alkenyl group Chemical group 0.000 claims description 18
- 125000004076 pyridyl group Chemical group 0.000 claims description 15
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 12
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 11
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- XCYVPMATTGSFTD-UHFFFAOYSA-N n-[4-[4-(6-oxo-1h-pyridazin-3-yl)phenyl]butyl]pyridine-3-carboxamide Chemical group C=1C=CN=CC=1C(=O)NCCCCC(C=C1)=CC=C1C=1C=CC(=O)NN=1 XCYVPMATTGSFTD-UHFFFAOYSA-N 0.000 claims description 3
- 239000000203 mixture Substances 0.000 description 53
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 45
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
- 239000000243 solution Substances 0.000 description 38
- 239000002904 solvent Substances 0.000 description 30
- 239000013078 crystal Substances 0.000 description 27
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- 239000007858 starting material Substances 0.000 description 23
- 238000000034 method Methods 0.000 description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- 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
- 238000006243 chemical reaction Methods 0.000 description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
- 230000036772 blood pressure Effects 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 239000003480 eluent Substances 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 125000006239 protecting group Chemical group 0.000 description 7
- 238000010898 silica gel chromatography Methods 0.000 description 7
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- MNZMECMQTYGSOI-UHFFFAOYSA-N acetic acid;hydron;bromide Chemical compound Br.CC(O)=O MNZMECMQTYGSOI-UHFFFAOYSA-N 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 230000002861 ventricular Effects 0.000 description 6
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- 206010040070 Septic Shock Diseases 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 201000008383 nephritis Diseases 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
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
- 125000003545 alkoxy 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
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- ZHWPTBJQTJMPJA-UHFFFAOYSA-N n-(4-phenylbutyl)acetamide Chemical compound CC(=O)NCCCCC1=CC=CC=C1 ZHWPTBJQTJMPJA-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-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
- 125000002252 acyl group Chemical group 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 210000005240 left ventricle Anatomy 0.000 description 3
- 230000003589 nefrotoxic effect Effects 0.000 description 3
- 231100000381 nephrotoxic Toxicity 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- 239000008213 purified water Substances 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 210000002966 serum Anatomy 0.000 description 3
- 238000006467 substitution reaction Methods 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
- 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 2
- VHCSBTPOPKFYIU-UHFFFAOYSA-N 2-chloroethanesulfonyl chloride Chemical compound ClCCS(Cl)(=O)=O VHCSBTPOPKFYIU-UHFFFAOYSA-N 0.000 description 2
- DWJWSJJJPOOPAQ-UHFFFAOYSA-N 2-methylsulfanyl-n-[3-[4-(6-oxo-1h-pyridazin-3-yl)phenyl]propyl]ethanesulfonamide Chemical compound C1=CC(CCCNS(=O)(=O)CCSC)=CC=C1C1=NNC(=O)C=C1 DWJWSJJJPOOPAQ-UHFFFAOYSA-N 0.000 description 2
- JORZGOKVVBFZAD-UHFFFAOYSA-N 3-[4-(4-aminobutoxy)phenyl]-1h-pyridazin-6-one;hydrobromide Chemical compound Br.C1=CC(OCCCCN)=CC=C1C1=NNC(=O)C=C1 JORZGOKVVBFZAD-UHFFFAOYSA-N 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
- BRXRQCVECRTQKF-UHFFFAOYSA-N 3-[4-(4-aminobutyl)-2-chloro-5-methylphenyl]-4,5-dihydro-1h-pyridazin-6-one Chemical compound C1=C(CCCCN)C(C)=CC(C=2CCC(=O)NN=2)=C1Cl BRXRQCVECRTQKF-UHFFFAOYSA-N 0.000 description 2
- 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 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
- 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 2
- 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 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- 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 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
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- 241001631457 Cannula Species 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-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
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- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
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- 230000001518 anti-nephritic effect Effects 0.000 description 2
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- 239000003146 anticoagulant agent Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
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- DCFKHNIGBAHNSS-UHFFFAOYSA-N chloro(triethyl)silane Chemical compound CC[Si](Cl)(CC)CC DCFKHNIGBAHNSS-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
- 239000003814 drug Substances 0.000 description 2
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- 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
- 230000005764 inhibitory process Effects 0.000 description 2
- WOFDVDFSGLBFAC-UHFFFAOYSA-N lactonitrile Chemical compound CC(O)C#N WOFDVDFSGLBFAC-UHFFFAOYSA-N 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
- 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 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
- 150000007522 mineralic acids Chemical class 0.000 description 2
- JDRMYOQETPMYQX-UHFFFAOYSA-N monomethyl succinate Chemical compound COC(=O)CCC(O)=O JDRMYOQETPMYQX-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
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- 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 201000006370 kidney failure Diseases 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 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
- 238000002156 mixing Methods 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 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 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
- BHYFJNXKFPIIFT-UHFFFAOYSA-N n-[3-[4-(6-oxo-1h-pyridazin-3-yl)phenoxy]propyl]pyridine-3-carboxamide Chemical compound C=1C=CN=CC=1C(=O)NCCCOC(C=C1)=CC=C1C=1C=CC(=O)NN=1 BHYFJNXKFPIIFT-UHFFFAOYSA-N 0.000 description 1
- NKFMCNRXNCDJFZ-UHFFFAOYSA-N n-[3-[4-(6-oxo-4,5-dihydro-1h-pyridazin-3-yl)phenoxy]propyl]pyridine-3-carboxamide Chemical compound C=1C=CN=CC=1C(=O)NCCCOC(C=C1)=CC=C1C1=NNC(=O)CC1 NKFMCNRXNCDJFZ-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
- DSUPCVQUEDSETP-UHFFFAOYSA-N n-[4-[4-(6-oxo-1h-pyridazin-3-yl)phenoxy]butyl]pyridine-3-carboxamide Chemical compound C=1C=CN=CC=1C(=O)NCCCCOC(C=C1)=CC=C1C=1C=CC(=O)NN=1 DSUPCVQUEDSETP-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
- 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
- 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
- 239000012038 nucleophile Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 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
- 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
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920013716 polyethylene resin Polymers 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 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
- 230000035485 pulse pressure Effects 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
- 230000006340 racemization Effects 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- 238000005932 reductive alkylation reaction Methods 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 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
- 239000007787 solid Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 239000003270 steroid hormone Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 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
- 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
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000005505 thiomorpholino group Chemical group 0.000 description 1
- DSNBHJFQCNUKMA-SCKDECHMSA-N thromboxane A2 Chemical compound OC(=O)CCC\C=C/C[C@@H]1[C@@H](/C=C/[C@@H](O)CCCCC)O[C@@H]2O[C@H]1C2 DSNBHJFQCNUKMA-SCKDECHMSA-N 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- 229920002554 vinyl polymer Polymers 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 (3)
| Publication Number | Publication Date |
|---|---|
| NO962643D0 NO962643D0 (no) | 1996-06-21 |
| NO962643L NO962643L (no) | 1996-12-30 |
| NO311084B1 true NO311084B1 (no) | 2001-10-08 |
Family
ID=26356726
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19962643A NO311084B1 (no) | 1995-06-27 | 1996-06-21 | Pyridazinonforbindelse |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US5698554A (fr) |
| EP (1) | EP0751132B1 (fr) |
| KR (1) | KR970061873A (fr) |
| CN (1) | CN1144802A (fr) |
| AR (1) | AR002602A1 (fr) |
| AT (1) | ATE195937T1 (fr) |
| AU (1) | AU694955B2 (fr) |
| BG (1) | BG62768B1 (fr) |
| CA (1) | CA2179939A1 (fr) |
| DE (1) | DE69610036T2 (fr) |
| DK (1) | DK0751132T3 (fr) |
| ES (1) | ES2151110T3 (fr) |
| GR (1) | GR3034910T3 (fr) |
| HU (1) | HUP9601766A3 (fr) |
| IL (1) | IL118631A (fr) |
| MY (1) | MY132263A (fr) |
| NO (1) | NO311084B1 (fr) |
| PT (1) | PT751132E (fr) |
| RU (1) | RU2131419C1 (fr) |
| SG (1) | SG46741A1 (fr) |
| TW (1) | TW432052B (fr) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2424551A1 (fr) * | 1997-05-27 | 1998-11-27 | Schneider (Usa) Inc. | Tuteur et endoprothese pour le traitement de vaisseaux sanguins ramifie |
| 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 |
| UA91602C2 (ru) * | 2006-03-17 | 2010-08-10 | Сумитомо Кемикал Компани, Лимитед | Пиридазиноновое производное, его применение в качестве гербицида и промежуточное соединение |
| PL2069312T3 (pl) * | 2006-07-25 | 2013-03-29 | Cephalon Inc | Pochodne pirydazynonu |
| ES2524787T3 (es) * | 2007-11-15 | 2014-12-12 | Msd Italia S.R.L. | Derivados de piridazinona como inhibidores de PARP |
| EP2547203A4 (fr) | 2010-03-19 | 2013-12-25 | Purdue Research Foundation | Modulateurs ccr5 pour traiter le vih |
| MX359640B (es) | 2010-11-05 | 2018-10-04 | Senomyx Inc | Compuestos utiles como moduladores de trpm8. |
| WO2012177896A1 (fr) | 2011-06-24 | 2012-12-27 | Amgen Inc. | Antagonistes de trpm8 et leur utilisation dans le cadre thérapeutique |
| PE20140868A1 (es) | 2011-06-24 | 2014-07-18 | Amgen Inc | Antagonistas trpm8 y su uso en tratamientos |
| WO2013097052A1 (fr) | 2011-12-30 | 2013-07-04 | Abbott Laboratories | Inhibiteurs de bromodomaine |
| US8952009B2 (en) | 2012-08-06 | 2015-02-10 | Amgen Inc. | Chroman derivatives as TRPM8 inhibitors |
| US10392371B2 (en) | 2015-10-01 | 2019-08-27 | Senomyx, Inc. | Compounds useful as modulators of TRPM8 |
| RU2741808C2 (ru) | 2016-04-15 | 2021-01-28 | Эббви Инк. | Ингибиторы бромодомена |
| AU2019372121A1 (en) * | 2018-10-30 | 2021-05-27 | Nuvation Bio Inc. | Heterocyclic compounds as BET inhibitors |
| 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 (16)
| 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 |
| EP0194548A3 (fr) * | 1985-03-12 | 1988-08-17 | Dr. Karl Thomae GmbH | Composés sulfonylaminoéthyl, médicament contenant ces composés et leur procédé de préparation |
| 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 |
| KR860007219A (ko) * | 1985-03-12 | 1986-10-08 | 베쩰, 좀머 | 설포닐아미노에틸 화합물의 제조방법 |
| 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 |
| 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 |
| CA2105067C (fr) | 1991-03-01 | 2002-05-14 | Kiyoshi Yoshida | Derive de l'indane et antagoniste de la thromboxane le contenant |
| CA2099743A1 (fr) * | 1992-07-02 | 1994-01-03 | Akihiko Ishida | Derives de la pyridazinone et procedes pour leur preparation |
| 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 (fr) * | 1993-12-28 | 1995-06-29 | Akihiko Ishida | Derive d'indane et procede de fabrication dudit derive |
| CA2139088A1 (fr) * | 1993-12-28 | 1995-06-29 | Akihiko Ishida | Derives indane, procedes pour leur preparation et intermediaires synthetiques pour ceux-ci |
-
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 RU RU96112778/04A patent/RU2131419C1/ru not_active IP Right Cessation
- 1996-06-26 CA CA002179939A patent/CA2179939A1/fr not_active Abandoned
- 1996-06-26 SG SG1996010164A patent/SG46741A1/en unknown
- 1996-06-26 MY MYPI96002583A patent/MY132263A/en unknown
- 1996-06-26 HU HU9601766A patent/HUP9601766A3/hu unknown
- 1996-06-27 DE DE69610036T patent/DE69610036T2/de not_active Expired - Fee Related
- 1996-06-27 PT PT96110412T patent/PT751132E/pt unknown
- 1996-06-27 KR KR1019960024718A patent/KR970061873A/ko not_active Application Discontinuation
- 1996-06-27 ES ES96110412T patent/ES2151110T3/es not_active Expired - Lifetime
- 1996-06-27 EP EP96110412A patent/EP0751132B1/fr not_active Expired - Lifetime
- 1996-06-27 AU AU56221/96A patent/AU694955B2/en not_active Ceased
- 1996-06-27 AT AT96110412T patent/ATE195937T1/de not_active IP Right Cessation
- 1996-06-27 CN CN96106873A patent/CN1144802A/zh active Pending
- 1996-06-27 BG BG100684A patent/BG62768B1/bg unknown
- 1996-06-27 US US08/671,485 patent/US5698554A/en not_active Expired - Fee Related
- 1996-06-27 DK DK96110412T patent/DK0751132T3/da active
-
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 |
|---|---|
| AU694955B2 (en) | 1998-08-06 |
| IL118631A (en) | 2002-05-23 |
| ES2151110T3 (es) | 2000-12-16 |
| EP0751132A1 (fr) | 1997-01-02 |
| CA2179939A1 (fr) | 1996-12-28 |
| EP0751132B1 (fr) | 2000-08-30 |
| BG100684A (bg) | 1997-03-31 |
| TW432052B (en) | 2001-05-01 |
| RU2131419C1 (ru) | 1999-06-10 |
| DE69610036T2 (de) | 2001-04-12 |
| IL118631A0 (en) | 1996-10-16 |
| US5698554A (en) | 1997-12-16 |
| BG62768B1 (bg) | 2000-07-31 |
| AU5622196A (en) | 1997-01-09 |
| HUP9601766A2 (en) | 1997-02-28 |
| US5808065A (en) | 1998-09-15 |
| NO962643D0 (no) | 1996-06-21 |
| MY132263A (en) | 2007-09-28 |
| SG46741A1 (en) | 1998-02-20 |
| HUP9601766A3 (en) | 1998-04-28 |
| ATE195937T1 (de) | 2000-09-15 |
| NO962643L (no) | 1996-12-30 |
| CN1144802A (zh) | 1997-03-12 |
| GR3034910T3 (en) | 2001-02-28 |
| DK0751132T3 (da) | 2000-11-13 |
| AR002602A1 (es) | 1998-03-25 |
| KR970061873A (ko) | 1997-09-12 |
| PT751132E (pt) | 2000-12-29 |
| HU9601766D0 (en) | 1996-08-28 |
| DE69610036D1 (de) | 2000-10-05 |
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