NO884332L - Cellebeskyttende stoffer. - Google Patents
Cellebeskyttende stoffer.Info
- Publication number
- NO884332L NO884332L NO88884332A NO884332A NO884332L NO 884332 L NO884332 L NO 884332L NO 88884332 A NO88884332 A NO 88884332A NO 884332 A NO884332 A NO 884332A NO 884332 L NO884332 L NO 884332L
- Authority
- NO
- Norway
- Prior art keywords
- ethenyl
- trans
- phthalazin
- methoxyphenyl
- starting materials
- Prior art date
Links
- 239000000126 substance Substances 0.000 title description 4
- 230000001681 protective effect Effects 0.000 title description 2
- -1 3-(dimethylamino)propyl Chemical group 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 25
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 19
- 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 18
- 238000002360 preparation method Methods 0.000 claims description 16
- 239000007858 starting material Substances 0.000 claims description 16
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 15
- IJAPPYDYQCXOEF-UHFFFAOYSA-N phthalazin-1(2H)-one Chemical compound C1=CC=C2C(=O)NN=CC2=C1 IJAPPYDYQCXOEF-UHFFFAOYSA-N 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 10
- QMONLZVJOOMKRW-UHFFFAOYSA-N 6-bromo-2h-phthalazin-1-one Chemical compound C1=NNC(=O)C=2C1=CC(Br)=CC=2 QMONLZVJOOMKRW-UHFFFAOYSA-N 0.000 claims description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 9
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 9
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 6
- 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 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 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 claims description 3
- 230000001476 alcoholic effect Effects 0.000 claims description 3
- 150000001350 alkyl halides Chemical class 0.000 claims description 3
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 claims description 3
- 239000002798 polar solvent Substances 0.000 claims description 3
- LCCONZDUKRETBL-FXRZFVDSSA-N 6-[(e)-2-(4-methoxyphenyl)ethenyl]-2-[3-(methylamino)propyl]phthalazin-1-one;hydrobromide Chemical group Br.C=1C=C2C(=O)N(CCCNC)N=CC2=CC=1\C=C\C1=CC=C(OC)C=C1 LCCONZDUKRETBL-FXRZFVDSSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 3
- SCKUBUKYIDMXMF-FXRZFVDSSA-N 2-[2-(dimethylamino)ethyl]-6-[(e)-2-(4-methoxyphenyl)ethenyl]phthalazin-1-one;hydrobromide Chemical compound Br.C1=CC(OC)=CC=C1\C=C\C1=CC=C2C(=O)N(CCN(C)C)N=CC2=C1 SCKUBUKYIDMXMF-FXRZFVDSSA-N 0.000 claims 1
- QSOIGHSAISYALC-UHDJGPCESA-N 2-[2-[di(propan-2-yl)amino]ethyl]-6-[(e)-2-(4-methoxyphenyl)ethenyl]phthalazin-1-one;hydrobromide Chemical compound Br.C1=CC(OC)=CC=C1\C=C\C1=CC=C2C(=O)N(CCN(C(C)C)C(C)C)N=CC2=C1 QSOIGHSAISYALC-UHDJGPCESA-N 0.000 claims 1
- YTXQBYPBEPWIME-FXRZFVDSSA-N 2-[3-(dimethylamino)propyl]-6-[(e)-2-(4-hydroxyphenyl)ethenyl]phthalazin-1-one;hydrochloride Chemical compound Cl.C=1C=C2C(=O)N(CCCN(C)C)N=CC2=CC=1\C=C\C1=CC=C(O)C=C1 YTXQBYPBEPWIME-FXRZFVDSSA-N 0.000 claims 1
- BLDWCKKQOMIUTM-IPZCTEOASA-N 2-[3-(dimethylamino)propyl]-6-[(e)-2-(4-methoxyphenyl)ethenyl]phthalazin-1-one;hydrobromide Chemical compound Br.C1=CC(OC)=CC=C1\C=C\C1=CC=C2C(=O)N(CCCN(C)C)N=CC2=C1 BLDWCKKQOMIUTM-IPZCTEOASA-N 0.000 claims 1
- 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 claims 1
- XKCCSNYPUMRLNR-UHDJGPCESA-N 2-[4-(dimethylamino)butyl]-6-[(e)-2-(4-methoxyphenyl)ethenyl]phthalazin-1-one;hydrobromide Chemical compound Br.C1=CC(OC)=CC=C1\C=C\C1=CC=C2C(=O)N(CCCCN(C)C)N=CC2=C1 XKCCSNYPUMRLNR-UHDJGPCESA-N 0.000 claims 1
- 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 claims 1
- AMGPDGVYCMLPJQ-ONEGZZNKSA-N 6-[(e)-2-(4-methoxyphenyl)ethenyl]-2-(1-methylpiperidin-4-yl)phthalazin-1-one Chemical compound C1=CC(OC)=CC=C1\C=C\C1=CC=C2C(=O)N(C3CCN(C)CC3)N=CC2=C1 AMGPDGVYCMLPJQ-ONEGZZNKSA-N 0.000 claims 1
- HTYGWZWNVXRUIR-UHDJGPCESA-N 6-[(e)-2-(4-methoxyphenyl)ethenyl]-2-(3-piperidin-1-ylpropyl)phthalazin-1-one;hydrobromide Chemical compound Br.C1=CC(OC)=CC=C1\C=C\C1=CC=C2C(=O)N(CCCN3CCCCC3)N=CC2=C1 HTYGWZWNVXRUIR-UHDJGPCESA-N 0.000 claims 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 46
- 239000000047 product Substances 0.000 description 43
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 14
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- 238000001953 recrystallisation Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- UAJRSHJHFRVGMG-UHFFFAOYSA-N 1-ethenyl-4-methoxybenzene Chemical compound COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 7
- 229960000905 indomethacin Drugs 0.000 description 7
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 238000004809 thin layer chromatography Methods 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000002552 dosage form Substances 0.000 description 5
- 230000003902 lesion Effects 0.000 description 5
- IUSXYVRFJVAVOB-UHFFFAOYSA-N n-(2-chloroethyl)-n-propan-2-ylpropan-2-amine;hydron;chloride Chemical compound Cl.CC(C)N(C(C)C)CCCl IUSXYVRFJVAVOB-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 4
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- MBBCGYVAAOLNCI-UHFFFAOYSA-N 4-(6-bromo-1-oxophthalazin-2-yl)butanoic acid Chemical compound BrC1=CC=C2C(=O)N(CCCC(=O)O)N=CC2=C1 MBBCGYVAAOLNCI-UHFFFAOYSA-N 0.000 description 3
- WNHUYRPTBAXYNM-UHFFFAOYSA-N 6-bromo-2-[2-(dimethylamino)ethyl]phthalazin-1-one Chemical compound BrC1=CC=C2C(=O)N(CCN(C)C)N=CC2=C1 WNHUYRPTBAXYNM-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000001120 cytoprotective effect Effects 0.000 description 3
- 230000002496 gastric effect Effects 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 210000002784 stomach Anatomy 0.000 description 3
- YUNYKJADHHPCLU-UHFFFAOYSA-N 2-(3-aminopropyl)-6-bromophthalazin-1-one Chemical compound BrC1=CC=C2C(=O)N(CCCN)N=CC2=C1 YUNYKJADHHPCLU-UHFFFAOYSA-N 0.000 description 2
- SJHFMWPLNZKCNX-UHFFFAOYSA-N 2-[2-(dimethylamino)ethyl]-6-[2-(4-methoxyphenyl)ethenyl]phthalazin-1-one Chemical compound C1=CC(OC)=CC=C1C=CC1=CC=C2C(=O)N(CCN(C)C)N=CC2=C1 SJHFMWPLNZKCNX-UHFFFAOYSA-N 0.000 description 2
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 2
- WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylamino-1-chloro-ethane hydrochloride Natural products CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 0.000 description 2
- LQLJZSJKRYTKTP-UHFFFAOYSA-N 2-dimethylaminoethyl chloride hydrochloride Chemical compound Cl.CN(C)CCCl LQLJZSJKRYTKTP-UHFFFAOYSA-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
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- HBRZRWOSLNEWCL-NSCUHMNNSA-N 6-[(e)-2-(4-methoxyphenyl)ethenyl]-2h-phthalazin-1-one Chemical compound C1=CC(OC)=CC=C1\C=C\C1=CC=C2C(=O)NN=CC2=C1 HBRZRWOSLNEWCL-NSCUHMNNSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 description 2
- 239000002260 anti-inflammatory agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- CCGSUNCLSOWKJO-UHFFFAOYSA-N cimetidine Chemical compound N#CNC(=N/C)\NCCSCC1=NC=N[C]1C CCGSUNCLSOWKJO-UHFFFAOYSA-N 0.000 description 2
- 229960001380 cimetidine Drugs 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- GSUCKVZTSXHESM-UHFFFAOYSA-N (1-methylpiperidin-4-yl)hydrazine Chemical compound CN1CCC(NN)CC1 GSUCKVZTSXHESM-UHFFFAOYSA-N 0.000 description 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical group C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- XDCMFRDBOXNZRH-UHFFFAOYSA-N 1-(3-chloropropyl)piperazine;hydrochloride Chemical compound Cl.ClCCCN1CCNCC1 XDCMFRDBOXNZRH-UHFFFAOYSA-N 0.000 description 1
- OBOBUDMMFXRNDO-UHFFFAOYSA-N 1-(3-chloropropyl)piperidine;hydron;chloride Chemical compound Cl.ClCCCN1CCCCC1 OBOBUDMMFXRNDO-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- ALGWSFMEKURBKU-BJILWQEISA-N 2-(3-aminopropyl)-6-[(e)-2-(4-methoxyphenyl)ethenyl]phthalazin-1-one;hydrobromide Chemical compound Br.C1=CC(OC)=CC=C1\C=C\C1=CC=C2C(=O)N(CCCN)N=CC2=C1 ALGWSFMEKURBKU-BJILWQEISA-N 0.000 description 1
- HDFMVHGMQMBXPU-AATRIKPKSA-N 2-[3-(dimethylamino)propyl]-6-[(e)-2-(4-methoxyphenyl)ethenyl]phthalazin-1-one Chemical compound C1=CC(OC)=CC=C1\C=C\C1=CC=C2C(=O)N(CCCN(C)C)N=CC2=C1 HDFMVHGMQMBXPU-AATRIKPKSA-N 0.000 description 1
- JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-UHFFFAOYSA-N 0.000 description 1
- GBHCABUWWQUMAJ-UHFFFAOYSA-N 2-hydrazinoethanol Chemical compound NNCCO GBHCABUWWQUMAJ-UHFFFAOYSA-N 0.000 description 1
- QOBSEQHCSOPUJX-UHFFFAOYSA-N 2H-phthalazin-1-one hydrobromide Chemical compound [Br-].OC1=[NH+]N=CC2=CC=CC=C12 QOBSEQHCSOPUJX-UHFFFAOYSA-N 0.000 description 1
- YUTKWFIHTBVNIE-UHFFFAOYSA-N 3-hydrazinyl-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCNN YUTKWFIHTBVNIE-UHFFFAOYSA-N 0.000 description 1
- 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 1
- GDHQNARWOJNUCD-UHFFFAOYSA-N 6-bromo-2-(3-piperidin-1-ylpropyl)phthalazin-1-one Chemical compound C=1C(Br)=CC=C(C2=O)C=1C=NN2CCCN1CCCCC1 GDHQNARWOJNUCD-UHFFFAOYSA-N 0.000 description 1
- XEEGHMXWNCNHAV-UHFFFAOYSA-N 6-bromo-2-[2-[di(propan-2-yl)amino]ethyl]phthalazin-1-one Chemical compound BrC1=CC=C2C(=O)N(CCN(C(C)C)C(C)C)N=CC2=C1 XEEGHMXWNCNHAV-UHFFFAOYSA-N 0.000 description 1
- WFIYCJPCSRUPES-UHFFFAOYSA-N 6-bromo-2-[4-(dimethylamino)butyl]phthalazin-1-one Chemical compound BrC1=CC=C2C(=O)N(CCCCN(C)C)N=CC2=C1 WFIYCJPCSRUPES-UHFFFAOYSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 208000018522 Gastrointestinal disease Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 208000008469 Peptic Ulcer Diseases 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 230000009858 acid secretion Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000000767 anti-ulcer Effects 0.000 description 1
- 239000003699 antiulcer agent Substances 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- XBPOBCXHALHJFP-UHFFFAOYSA-N ethyl 4-bromobutanoate Chemical compound CCOC(=O)CCCBr XBPOBCXHALHJFP-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 210000001156 gastric mucosa Anatomy 0.000 description 1
- 230000000762 glandular Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012943 hotmelt Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 239000002731 stomach secretion inhibitor Substances 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
-
- 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10270387A | 1987-09-30 | 1987-09-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO884332D0 NO884332D0 (no) | 1988-09-29 |
| NO884332L true NO884332L (no) | 1989-03-31 |
Family
ID=22291251
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO88884332A NO884332L (no) | 1987-09-30 | 1988-09-29 | Cellebeskyttende stoffer. |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP0309765A3 (de) |
| JP (1) | JPH01132519A (de) |
| KR (1) | KR890004706A (de) |
| AU (1) | AU2196188A (de) |
| DK (1) | DK544288A (de) |
| FI (1) | FI884483A (de) |
| IL (1) | IL87865A0 (de) |
| NO (1) | NO884332L (de) |
| PT (1) | PT88651A (de) |
| ZA (1) | ZA887306B (de) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL383550A1 (pl) * | 2007-10-15 | 2009-04-27 | Uniwersytet Łódzki | Nowe pochodne benzeno- i pirydopirydazynonów |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5661365A (en) * | 1979-10-26 | 1981-05-26 | Showa Denko Kk | Dimethoxyphthalazinone derivative and its preparation |
| JPS5728064A (en) * | 1980-07-29 | 1982-02-15 | Morishita Seiyaku Kk | Phthalazinone derivative |
| US4665181A (en) * | 1984-05-17 | 1987-05-12 | Pennwalt Corporation | Anti-inflammatory phthalazinones |
-
1988
- 1988-09-02 EP EP19880114355 patent/EP0309765A3/de not_active Withdrawn
- 1988-09-07 AU AU21961/88A patent/AU2196188A/en not_active Abandoned
- 1988-09-28 IL IL87865A patent/IL87865A0/xx unknown
- 1988-09-29 ZA ZA887306A patent/ZA887306B/xx unknown
- 1988-09-29 NO NO88884332A patent/NO884332L/no unknown
- 1988-09-29 KR KR1019880012581A patent/KR890004706A/ko not_active Application Discontinuation
- 1988-09-29 DK DK544288A patent/DK544288A/da not_active Application Discontinuation
- 1988-09-29 FI FI884483A patent/FI884483A/fi not_active Application Discontinuation
- 1988-09-30 JP JP63244653A patent/JPH01132519A/ja active Pending
- 1988-09-30 PT PT88651A patent/PT88651A/pt not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| IL87865A0 (en) | 1989-03-31 |
| DK544288D0 (da) | 1988-09-29 |
| FI884483A (fi) | 1989-03-31 |
| EP0309765A3 (de) | 1990-09-26 |
| PT88651A (pt) | 1989-07-31 |
| NO884332D0 (no) | 1988-09-29 |
| KR890004706A (ko) | 1989-05-09 |
| FI884483A0 (fi) | 1988-09-29 |
| ZA887306B (en) | 1989-07-26 |
| EP0309765A2 (de) | 1989-04-05 |
| JPH01132519A (ja) | 1989-05-25 |
| AU2196188A (en) | 1989-04-06 |
| DK544288A (da) | 1989-03-31 |
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