NO851938L - Fremgangsmaate ved fremstilling av et ftalazinonderivat. - Google Patents
Fremgangsmaate ved fremstilling av et ftalazinonderivat.Info
- Publication number
- NO851938L NO851938L NO851938A NO851938A NO851938L NO 851938 L NO851938 L NO 851938L NO 851938 A NO851938 A NO 851938A NO 851938 A NO851938 A NO 851938A NO 851938 L NO851938 L NO 851938L
- Authority
- NO
- Norway
- Prior art keywords
- compound
- hydrogen
- formula
- phthalazinone
- ethenyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 25
- 150000003020 phtalazines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 35
- -1 alkali metal salt Chemical class 0.000 claims abstract description 34
- 239000001257 hydrogen Substances 0.000 claims abstract description 34
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 23
- 125000000217 alkyl group Chemical class 0.000 claims abstract description 22
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 19
- IJAPPYDYQCXOEF-UHFFFAOYSA-N phthalazin-1(2H)-one Chemical group C1=CC=C2C(=O)NN=CC2=C1 IJAPPYDYQCXOEF-UHFFFAOYSA-N 0.000 claims abstract description 19
- 150000002148 esters Chemical class 0.000 claims abstract description 10
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
- 125000003545 alkoxy group Chemical class 0.000 claims abstract description 9
- 239000002253 acid Substances 0.000 claims abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000006294 amino alkylene group Chemical group 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical class 0.000 claims abstract description 6
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 5
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims abstract description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 3
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000011707 mineral Substances 0.000 claims abstract description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 65
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 55
- 239000000203 mixture Substances 0.000 claims description 45
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 31
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 claims description 18
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
- 238000010992 reflux Methods 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- UAJRSHJHFRVGMG-UHFFFAOYSA-N 1-ethenyl-4-methoxybenzene Chemical compound COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-UHFFFAOYSA-N 0.000 claims description 8
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 5
- HJPAMEIHXKSDRO-UHFFFAOYSA-N 5-bromo-3-hydroxy-3h-2-benzofuran-1-one Chemical compound C1=C(Br)C=C2C(O)OC(=O)C2=C1 HJPAMEIHXKSDRO-UHFFFAOYSA-N 0.000 claims description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 4
- 239000005977 Ethylene Substances 0.000 claims description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 4
- 239000012312 sodium hydride Substances 0.000 claims description 4
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 4
- OANUPTAWUITAKT-UHFFFAOYSA-N 3-hydroxy-5-[2-(4-methoxyphenyl)ethenyl]-3h-2-benzofuran-1-one Chemical compound C1=CC(OC)=CC=C1C=CC1=CC=C(C(=O)OC2O)C2=C1 OANUPTAWUITAKT-UHFFFAOYSA-N 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 3
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 claims description 3
- 239000002585 base Substances 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 150000004714 phosphonium salts Chemical class 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 3
- 229910019142 PO4 Inorganic materials 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 2
- 239000010452 phosphate Substances 0.000 claims 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims 2
- HSDSKVWQTONQBJ-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)ethanone Chemical compound CC(=O)C1=CC=C(C)C=C1C HSDSKVWQTONQBJ-UHFFFAOYSA-N 0.000 claims 1
- FBPINGSGHKXIQA-UHFFFAOYSA-N 2-amino-3-(2-carboxyethylsulfanyl)propanoic acid Chemical compound OC(=O)C(N)CSCCC(O)=O FBPINGSGHKXIQA-UHFFFAOYSA-N 0.000 claims 1
- HBRZRWOSLNEWCL-UHFFFAOYSA-N 6-[2-(4-methoxyphenyl)ethenyl]-2h-phthalazin-1-one Chemical compound C1=CC(OC)=CC=C1C=CC1=CC=C2C(=O)NN=CC2=C1 HBRZRWOSLNEWCL-UHFFFAOYSA-N 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 150000001350 alkyl halides Chemical class 0.000 claims 1
- 125000005997 bromomethyl group Chemical group 0.000 claims 1
- LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 241001465754 Metazoa Species 0.000 abstract description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 abstract description 2
- 239000002260 anti-inflammatory agent Substances 0.000 abstract description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 61
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 46
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 46
- 239000000047 product Substances 0.000 description 46
- 239000000243 solution Substances 0.000 description 43
- 238000002844 melting Methods 0.000 description 32
- 230000008018 melting Effects 0.000 description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 230000015572 biosynthetic process Effects 0.000 description 26
- 239000007787 solid Substances 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 23
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- 238000003756 stirring Methods 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000000706 filtrate Substances 0.000 description 12
- 238000001953 recrystallisation Methods 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 241000894007 species Species 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 239000002002 slurry Substances 0.000 description 8
- 239000000679 carrageenan Substances 0.000 description 7
- 229940113118 carrageenan Drugs 0.000 description 7
- 235000010418 carrageenan Nutrition 0.000 description 7
- 229920001525 carrageenan Polymers 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 230000005764 inhibitory process Effects 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 7
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 6
- OANUPTAWUITAKT-NSCUHMNNSA-N 3-hydroxy-5-[(e)-2-(4-methoxyphenyl)ethenyl]-3h-2-benzofuran-1-one Chemical compound C1=CC(OC)=CC=C1\C=C\C1=CC=C(C(=O)OC2O)C2=C1 OANUPTAWUITAKT-NSCUHMNNSA-N 0.000 description 5
- GBQXGTOBNYIUJC-OWOJBTEDSA-N 6-[(e)-2-(4-hydroxyphenyl)ethenyl]-2h-phthalazin-1-one Chemical compound C1=CC(O)=CC=C1\C=C\C1=CC=C2C(=O)NN=CC2=C1 GBQXGTOBNYIUJC-OWOJBTEDSA-N 0.000 description 5
- 206010030113 Oedema Diseases 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 3
- LOTXHMSFJJFFRP-OWOJBTEDSA-N 4-[(e)-2-(1-oxo-2h-phthalazin-6-yl)ethenyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1\C=C\C1=CC=C2C(=O)NN=CC2=C1 LOTXHMSFJJFFRP-OWOJBTEDSA-N 0.000 description 3
- GDWUNKJJSAKJSC-UHFFFAOYSA-N 6-iodo-3h-2-benzofuran-1-one Chemical compound IC1=CC=C2COC(=O)C2=C1 GDWUNKJJSAKJSC-UHFFFAOYSA-N 0.000 description 3
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 210000002683 foot Anatomy 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- BNXIFKJTDCPIDP-MDZDMXLPSA-N 2-[3-(dimethylamino)propyl]-6-[(e)-2-phenylethenyl]phthalazin-1-one Chemical compound C=1C=C2C(=O)N(CCCN(C)C)N=CC2=CC=1\C=C\C1=CC=CC=C1 BNXIFKJTDCPIDP-MDZDMXLPSA-N 0.000 description 2
- LJQNMDZRCXJETK-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine;hydron;chloride Chemical compound Cl.CN(C)CCCCl LJQNMDZRCXJETK-UHFFFAOYSA-N 0.000 description 2
- YUTKWFIHTBVNIE-UHFFFAOYSA-N 3-hydrazinyl-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCNN YUTKWFIHTBVNIE-UHFFFAOYSA-N 0.000 description 2
- HBAPYYQLLJZRJB-OWOJBTEDSA-N 3-hydroxy-5-[(e)-2-(4-nitrophenyl)ethenyl]-3h-2-benzofuran-1-one Chemical group C1=C2C(O)OC(=O)C2=CC=C1\C=C\C1=CC=C([N+]([O-])=O)C=C1 HBAPYYQLLJZRJB-OWOJBTEDSA-N 0.000 description 2
- BJJUJLDHJVKAFZ-VOTSOKGWSA-N 3-hydroxy-5-[(e)-2-phenylethenyl]-3h-2-benzofuran-1-one Chemical compound C1=C2C(O)OC(=O)C2=CC=C1\C=C\C1=CC=CC=C1 BJJUJLDHJVKAFZ-VOTSOKGWSA-N 0.000 description 2
- RIOSVKNSRZEEKC-UHFFFAOYSA-N 3-hydroxy-6-[2-(4-methoxyphenyl)ethenyl]-3h-2-benzofuran-1-one Chemical compound C1=CC(OC)=CC=C1C=CC1=CC=C(C(O)OC2=O)C2=C1 RIOSVKNSRZEEKC-UHFFFAOYSA-N 0.000 description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
- ZJLCWVMRMKUIEQ-OWOJBTEDSA-N 5-[(e)-2-(4-chlorophenyl)ethenyl]-3-hydroxy-3h-2-benzofuran-1-one Chemical group C1=C2C(O)OC(=O)C2=CC=C1\C=C\C1=CC=C(Cl)C=C1 ZJLCWVMRMKUIEQ-OWOJBTEDSA-N 0.000 description 2
- ISMUWQMUWFPFBZ-UHFFFAOYSA-N 5-amino-3h-2-benzofuran-1-one Chemical compound NC1=CC=C2C(=O)OCC2=C1 ISMUWQMUWFPFBZ-UHFFFAOYSA-N 0.000 description 2
- IUSPXLCLQIZFHL-UHFFFAOYSA-N 5-bromo-3h-2-benzofuran-1-one Chemical compound BrC1=CC=C2C(=O)OCC2=C1 IUSPXLCLQIZFHL-UHFFFAOYSA-N 0.000 description 2
- ZVZSOJGUVOORQH-SNAWJCMRSA-N 6-[(e)-2-(4-chlorophenyl)ethenyl]-2-[3-(dimethylamino)propyl]phthalazin-1-one Chemical compound C=1C=C2C(=O)N(CCCN(C)C)N=CC2=CC=1\C=C\C1=CC=C(Cl)C=C1 ZVZSOJGUVOORQH-SNAWJCMRSA-N 0.000 description 2
- PHMNPPIIRCUSDY-AATRIKPKSA-N 6-[(e)-2-(4-methoxyphenyl)ethenyl]-2-pyridin-2-ylphthalazin-1-one Chemical compound C1=CC(OC)=CC=C1\C=C\C1=CC=C2C(=O)N(C=3N=CC=CC=3)N=CC2=C1 PHMNPPIIRCUSDY-AATRIKPKSA-N 0.000 description 2
- CZSXPMCKPBWSMK-VOTSOKGWSA-N 6-[(e)-2-phenylethenyl]-2h-phthalazin-1-one Chemical group C=1C=C2C(=O)NN=CC2=CC=1\C=C\C1=CC=CC=C1 CZSXPMCKPBWSMK-VOTSOKGWSA-N 0.000 description 2
- GBQXGTOBNYIUJC-UHFFFAOYSA-N 6-[2-(4-hydroxyphenyl)ethenyl]-2h-phthalazin-1-one Chemical compound C1=CC(O)=CC=C1C=CC1=CC=C2C(=O)NN=CC2=C1 GBQXGTOBNYIUJC-UHFFFAOYSA-N 0.000 description 2
- ODGMUABZVCNDPB-UHFFFAOYSA-N 6-[2-(4-methylphenyl)ethenyl]-2h-phthalazin-1-one Chemical compound C1=CC(C)=CC=C1C=CC1=CC=C2C(=O)NN=CC2=C1 ODGMUABZVCNDPB-UHFFFAOYSA-N 0.000 description 2
- DQCPJGKFWJNHPC-UHFFFAOYSA-N 6-[2-(4-nitrophenyl)ethenyl]-2h-phthalazin-1-one Chemical compound C1=CC([N+](=O)[O-])=CC=C1C=CC1=CC=C2C(=O)NN=CC2=C1 DQCPJGKFWJNHPC-UHFFFAOYSA-N 0.000 description 2
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- 235000010755 mineral Nutrition 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 230000009935 nitrosation Effects 0.000 description 1
- 238000007034 nitrosation reaction Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- PMOIAJVKYNVHQE-UHFFFAOYSA-N phosphanium;bromide Chemical compound [PH4+].[Br-] PMOIAJVKYNVHQE-UHFFFAOYSA-N 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
- C07D237/30—Phthalazines
-
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
- C07D237/30—Phthalazines
- C07D237/32—Phthalazines with oxygen atoms directly attached to carbon atoms of the nitrogen-containing ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Pharmacology & Pharmacy (AREA)
- Rheumatology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/611,310 US4665181A (en) | 1984-05-17 | 1984-05-17 | Anti-inflammatory phthalazinones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO851938L true NO851938L (no) | 1985-11-18 |
Family
ID=24448523
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO851938A NO851938L (no) | 1984-05-17 | 1985-05-14 | Fremgangsmaate ved fremstilling av et ftalazinonderivat. |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4665181A (ja) |
| EP (1) | EP0164593B1 (ja) |
| JP (1) | JPS60255777A (ja) |
| KR (1) | KR850008668A (ja) |
| AT (1) | ATE47998T1 (ja) |
| AU (1) | AU570549B2 (ja) |
| DE (2) | DE164593T1 (ja) |
| DK (1) | DK215485A (ja) |
| FI (1) | FI851959L (ja) |
| IL (1) | IL74805A (ja) |
| NO (1) | NO851938L (ja) |
| NZ (1) | NZ211589A (ja) |
| PH (1) | PH23246A (ja) |
| ZA (1) | ZA852387B (ja) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE49205T1 (de) * | 1984-09-14 | 1990-01-15 | Asta Pharma Ag | Substituierte benzylphthalazinon-derivate. |
| US4769369A (en) * | 1986-11-14 | 1988-09-06 | Pennwalt Corporation | Anti-allergy 1(2H)-phthalazinones |
| EP0309765A3 (en) * | 1987-09-30 | 1990-09-26 | Fisons Corporation | 1(2h)-phthalazinones as cytoprotective agents |
| DE4103405A1 (de) * | 1991-02-05 | 1992-08-06 | Basf Ag | 3-amino-benzol-1,2,4,5-tetracarbonsaeuredihydrazide und ihre verwendung als chemilumineszenz-faehige verbindugnen sowie 3-amino-benzol-1,2,4,5-tetracarbonsaeuredianhydride |
| DE4207234A1 (de) * | 1992-03-07 | 1993-09-09 | Asta Medica Ag | Neue aminocarbonsaeure-derivate mit antiallergischer/antiasthmatischer wirkung und verfahren zu deren herstellung |
| CH683965A5 (it) * | 1993-02-19 | 1994-06-30 | Limad Marketing Exp & Imp | Composti della classe dei ftalidrazidici come sostanza attiva in agenti antinfiammatori ed antitossici. |
| EP0934933A1 (en) * | 1998-02-06 | 1999-08-11 | Byk Gulden Lomberg Chemische Fabrik GmbH | Phthalazinones |
| ES2265929T3 (es) * | 1999-03-30 | 2007-03-01 | Novartis Ag | Derivados de ftalazina para el tratamiento de enfermedades inflamatorias. |
| DK1246813T3 (da) * | 1999-12-30 | 2004-03-01 | Lundbeck & Co As H | Fremgangsmåde til fremstilling af Citalopram |
| US7151102B2 (en) * | 2000-10-30 | 2006-12-19 | Kudos Pharmaceuticals Limited | Phthalazinone derivatives |
| GB0111078D0 (en) * | 2001-05-04 | 2001-06-27 | Novartis Ag | Organic compounds |
| CA2482806A1 (en) * | 2002-04-30 | 2003-11-13 | Kudos Pharmaceuticals Limited | Phthalazinone derivatives |
| GB0223341D0 (en) * | 2002-10-08 | 2002-11-13 | Groningen Acad Ziekenhuis | Organic compounds |
| GB0305681D0 (en) | 2003-03-12 | 2003-04-16 | Kudos Pharm Ltd | Phthalazinone derivatives |
| US7449464B2 (en) * | 2003-03-12 | 2008-11-11 | Kudos Pharmaceuticals Limited | Phthalazinone derivatives |
| GB0419072D0 (en) | 2004-08-26 | 2004-09-29 | Kudos Pharm Ltd | Phthalazinone derivatives |
| US20070020330A1 (en) | 2004-11-24 | 2007-01-25 | Medpointe Healthcare Inc. | Compositions comprising azelastine and methods of use thereof |
| MX2007006233A (es) | 2004-11-24 | 2007-11-23 | Medpointe Healthcare Inc | Composiciones que comprenden azelastina y metodos de uso de la misma. |
| US8758816B2 (en) | 2004-11-24 | 2014-06-24 | Meda Pharmaceuticals Inc. | Compositions comprising azelastine and methods of use thereof |
| GB0428111D0 (en) * | 2004-12-22 | 2005-01-26 | Kudos Pharm Ltd | Pthalazinone derivatives |
| US7759337B2 (en) * | 2005-03-03 | 2010-07-20 | Amgen Inc. | Phthalazine compounds and methods of use |
| WO2006103550A1 (en) * | 2005-03-31 | 2006-10-05 | Ranbaxy Laboratories Limited | Processes for the preparation of citalopram and its intermediate 5-aminophthalide |
| GB0521373D0 (en) | 2005-10-20 | 2005-11-30 | Kudos Pharm Ltd | Pthalazinone derivatives |
| JP2009541217A (ja) * | 2006-06-15 | 2009-11-26 | クドス ファーマシューティカルズ リミテッド | Ｐａｒｐ阻害剤としての２−オキシベンズアミド誘導体 |
| EP2041110A1 (en) * | 2006-06-15 | 2009-04-01 | Kudos Pharmaceuticals Limited | 2 -oxyheteroarylamide derivatives as parp inhibitors |
| JP2009539963A (ja) * | 2006-06-15 | 2009-11-19 | クドス ファーマシューティカルズ リミテッド | Ｐａｒｐ阻害剤 |
| GB0619325D0 (en) | 2006-09-30 | 2006-11-08 | Univ Strathclyde | New compounds |
| UY30639A1 (es) * | 2006-10-17 | 2008-05-31 | Kudos Pharm Ltd | Derivados sustituidos de 2h-ftalazin-1-ona, sus formas cristalinas, proceso de preparacion y aplicaciones |
| US20080280910A1 (en) * | 2007-03-22 | 2008-11-13 | Keith Allan Menear | Phthalazinone derivatives |
| TW200900396A (en) * | 2007-04-10 | 2009-01-01 | Kudos Pharm Ltd | Phthalazinone derivatives |
| US20090023727A1 (en) * | 2007-07-05 | 2009-01-22 | Muhammad Hashim Javaid | Phthalazinone derivatives |
| EP2188278A1 (en) | 2007-09-14 | 2010-05-26 | AstraZeneca AB | Phthalazinone derivatives |
| MX2010004028A (es) * | 2007-10-17 | 2010-04-30 | Kudos Pharm Ltd | 4-[3-(4-ciclopropancarbonil-piperacin-1-carbonil)-4-fluoro-bencil ]-2h-ftalacin-1-ona. |
| AR070221A1 (es) | 2008-01-23 | 2010-03-25 | Astrazeneca Ab | Derivados de ftalazinona inhibidores de polimerasas, composiciones farmaceuticas que los contienen y usos de los mismos para prevenir y/o tratar tumores cancerigenos,lesiones isquemicas y otras enfermedades asociadas. |
| HUE030800T2 (en) | 2008-10-07 | 2017-05-29 | Astrazeneca Uk Ltd | Pharmaceutical Form No. 514 |
| UY32790A (es) * | 2009-07-15 | 2011-02-28 | Astrazeneca Ab | Compuesto de ftalazinona |
| MX361350B (es) * | 2011-05-10 | 2018-12-04 | Gilead Sciences Inc | Compuestos heterocíclicos fusionados como moduladores del canal de sodio. |
| CA2906008C (en) | 2013-03-13 | 2019-07-09 | Flatley Discovery Lab, Llc | Pyridazinone compounds and methods for the treatment of cystic fibrosis |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB808636A (en) * | 1955-08-02 | 1959-02-11 | Cassella Farbwerke Mainkur Ag | Basically substituted heterocyclic compounds |
| GB1126669A (en) * | 1967-04-28 | 1968-09-11 | Deutsches Hydrierwerke Rodlebe | Process for production of basically substituted phthalazones |
| DE2114884A1 (de) * | 1971-03-27 | 1972-10-12 | Cassella Farbwerke Mainkur Ag, 6000 Frankfurt | Basisch substituierte Derivate des 1(2H)-Phthalazinons |
| JPS4931683A (ja) * | 1972-07-27 | 1974-03-22 | ||
| JPS5214788A (en) * | 1975-07-21 | 1977-02-03 | Fuji Photo Film Co Ltd | Process for preparing phthalazinone and its derivatives |
| US4134880A (en) * | 1978-01-19 | 1979-01-16 | Mitsui Toatsu Chemicals, Incorporated | Process for producing an aromatic urethane from nitro compounds, hydroxyl compounds and carbon monoxide using metal-Lewis acid-ammonia catalyst systems |
| US4334069A (en) * | 1978-07-24 | 1982-06-08 | Miles Laboratories, Inc. | Chemiluminescent phthalhydrazide-labeled hapten conjugates |
| US4293553A (en) * | 1978-08-11 | 1981-10-06 | Masayuki Ishikawa | 1-Phthalazone derivatives, and use thereof |
| CA1143733A (en) * | 1979-07-31 | 1983-03-29 | Masao Yoshida | Producing 7-alkoxycarbonyl-6,8-dimethyl-4- hydroxymethyl-1-phthalazone and intermediates |
-
1984
- 1984-05-17 US US06/611,310 patent/US4665181A/en not_active Expired - Fee Related
-
1985
- 1985-03-26 NZ NZ211589A patent/NZ211589A/xx unknown
- 1985-03-29 ZA ZA852387A patent/ZA852387B/xx unknown
- 1985-04-01 PH PH32079A patent/PH23246A/en unknown
- 1985-04-03 IL IL74805A patent/IL74805A/xx unknown
- 1985-04-04 AU AU40873/85A patent/AU570549B2/en not_active Ceased
- 1985-05-13 EP EP85105873A patent/EP0164593B1/en not_active Expired
- 1985-05-13 DE DE198585105873T patent/DE164593T1/de active Pending
- 1985-05-13 DE DE8585105873T patent/DE3574253D1/de not_active Expired
- 1985-05-13 AT AT85105873T patent/ATE47998T1/de not_active IP Right Cessation
- 1985-05-14 NO NO851938A patent/NO851938L/no unknown
- 1985-05-15 KR KR1019850003318A patent/KR850008668A/ko not_active Application Discontinuation
- 1985-05-15 DK DK215485A patent/DK215485A/da not_active Application Discontinuation
- 1985-05-16 FI FI851959A patent/FI851959L/fi not_active Application Discontinuation
- 1985-05-17 JP JP60104183A patent/JPS60255777A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US4665181A (en) | 1987-05-12 |
| EP0164593A1 (en) | 1985-12-18 |
| KR850008668A (ko) | 1985-12-21 |
| ZA852387B (en) | 1986-04-30 |
| AU4087385A (en) | 1985-11-21 |
| DK215485A (da) | 1985-11-18 |
| PH23246A (en) | 1989-06-16 |
| NZ211589A (en) | 1988-06-30 |
| JPS60255777A (ja) | 1985-12-17 |
| EP0164593B1 (en) | 1989-11-15 |
| DE164593T1 (de) | 1986-06-12 |
| AU570549B2 (en) | 1988-03-17 |
| IL74805A (en) | 1988-07-31 |
| ATE47998T1 (de) | 1989-12-15 |
| DE3574253D1 (de) | 1989-12-21 |
| FI851959A0 (fi) | 1985-05-16 |
| IL74805A0 (en) | 1985-07-31 |
| DK215485D0 (da) | 1985-05-15 |
| FI851959L (fi) | 1985-11-18 |
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