JPS6242901B2 - - Google Patents
Info
- Publication number
- JPS6242901B2 JPS6242901B2 JP13043479A JP13043479A JPS6242901B2 JP S6242901 B2 JPS6242901 B2 JP S6242901B2 JP 13043479 A JP13043479 A JP 13043479A JP 13043479 A JP13043479 A JP 13043479A JP S6242901 B2 JPS6242901 B2 JP S6242901B2
- Authority
- JP
- Japan
- Prior art keywords
- phenylphthalazine
- compound
- group
- formula
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- KHIILJVSYUGMSE-UHFFFAOYSA-N 1-phenylphthalazine Chemical class C1=CC=CC=C1C1=NN=CC2=CC=CC=C12 KHIILJVSYUGMSE-UHFFFAOYSA-N 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 description 25
- -1 n -butyl Chemical group 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- GGWBHVILAJZWKJ-KJEVSKRMSA-N ranitidine hydrochloride Chemical compound [H+].[Cl-].[O-][N+](=O)\C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 GGWBHVILAJZWKJ-KJEVSKRMSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- DOMCJMIKKKNQRH-UHFFFAOYSA-N 1-(2-methylphenoxy)-4-phenylphthalazine Chemical compound CC1=CC=CC=C1OC(C1=CC=CC=C11)=NN=C1C1=CC=CC=C1 DOMCJMIKKKNQRH-UHFFFAOYSA-N 0.000 description 3
- WJJDLSHYLZRFDD-UHFFFAOYSA-N 1-chloro-4-phenylphthalazine Chemical compound C12=CC=CC=C2C(Cl)=NN=C1C1=CC=CC=C1 WJJDLSHYLZRFDD-UHFFFAOYSA-N 0.000 description 3
- MXBPGYQJSPGSHX-UHFFFAOYSA-N 1-phenyl-4-(2,4,6-trimethylphenoxy)phthalazine Chemical compound Cc1cc(C)c(Oc2nnc(-c3ccccc3)c3ccccc23)c(C)c1 MXBPGYQJSPGSHX-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 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
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- BVTBLVPEMCWJPX-UHFFFAOYSA-N 1-(2,3-dimethylphenoxy)-4-phenylphthalazine Chemical compound CC1=CC=CC(OC=2C3=CC=CC=C3C(C=3C=CC=CC=3)=NN=2)=C1C BVTBLVPEMCWJPX-UHFFFAOYSA-N 0.000 description 2
- MGNMFYVAYYJIPN-UHFFFAOYSA-N 1-(2,5-dichlorophenoxy)-4-phenylphthalazine Chemical compound ClC1=CC=C(Cl)C(OC=2C3=CC=CC=C3C(C=3C=CC=CC=3)=NN=2)=C1 MGNMFYVAYYJIPN-UHFFFAOYSA-N 0.000 description 2
- MWOVZLDGMRXYCS-UHFFFAOYSA-N 1-(2,5-diethylphenoxy)-4-phenylphthalazine Chemical compound CCC1=CC=C(CC)C(OC=2C3=CC=CC=C3C(C=3C=CC=CC=3)=NN=2)=C1 MWOVZLDGMRXYCS-UHFFFAOYSA-N 0.000 description 2
- NHSRKHZYSHMDJN-UHFFFAOYSA-N 1-(2,5-difluorophenoxy)-4-phenylphthalazine Chemical compound FC1=CC=C(F)C(OC=2C3=CC=CC=C3C(C=3C=CC=CC=3)=NN=2)=C1 NHSRKHZYSHMDJN-UHFFFAOYSA-N 0.000 description 2
- ZWOWQQDULRTHNW-UHFFFAOYSA-N 1-(2,5-dimethoxyphenoxy)-4-phenylphthalazine Chemical compound COC1=CC=C(OC)C(OC=2C3=CC=CC=C3C(C=3C=CC=CC=3)=NN=2)=C1 ZWOWQQDULRTHNW-UHFFFAOYSA-N 0.000 description 2
- YORUYWHVRRWGQX-UHFFFAOYSA-N 1-(2,5-dipropylphenoxy)-4-phenylphthalazine Chemical compound CCCC1=CC=C(CCC)C(OC=2C3=CC=CC=C3C(C=3C=CC=CC=3)=NN=2)=C1 YORUYWHVRRWGQX-UHFFFAOYSA-N 0.000 description 2
- PMFAZAUPKYLWFQ-UHFFFAOYSA-N 1-(2,6-dichlorophenoxy)-4-phenylphthalazine Chemical compound ClC1=CC=CC(Cl)=C1OC(C1=CC=CC=C11)=NN=C1C1=CC=CC=C1 PMFAZAUPKYLWFQ-UHFFFAOYSA-N 0.000 description 2
- XULLEBJAVLJYCY-UHFFFAOYSA-N 1-(2-chlorophenoxy)-4-phenylphthalazine Chemical compound ClC1=CC=CC=C1OC(C1=CC=CC=C11)=NN=C1C1=CC=CC=C1 XULLEBJAVLJYCY-UHFFFAOYSA-N 0.000 description 2
- PDYIUMVWCBAEMJ-UHFFFAOYSA-N 1-(2-ethylphenoxy)-4-phenylphthalazine Chemical compound CCC1=CC=CC=C1OC(C1=CC=CC=C11)=NN=C1C1=CC=CC=C1 PDYIUMVWCBAEMJ-UHFFFAOYSA-N 0.000 description 2
- VBSCNAAFFFZKAZ-UHFFFAOYSA-N 1-(3,4-dimethoxyphenoxy)-4-phenylphthalazine Chemical compound C1=C(OC)C(OC)=CC=C1OC(C1=CC=CC=C11)=NN=C1C1=CC=CC=C1 VBSCNAAFFFZKAZ-UHFFFAOYSA-N 0.000 description 2
- LDHZNIMIVNNHSD-UHFFFAOYSA-N 1-(3-bromophenoxy)-4-phenylphthalazine Chemical compound BrC1=CC=CC(OC=2C3=CC=CC=C3C(C=3C=CC=CC=3)=NN=2)=C1 LDHZNIMIVNNHSD-UHFFFAOYSA-N 0.000 description 2
- XSGNJHXFWOGNOG-UHFFFAOYSA-N 1-(3-butoxyphenoxy)-4-phenylphthalazine Chemical compound CCCCOC1=CC=CC(OC=2C3=CC=CC=C3C(C=3C=CC=CC=3)=NN=2)=C1 XSGNJHXFWOGNOG-UHFFFAOYSA-N 0.000 description 2
- MMBCCBHIMLNMOI-UHFFFAOYSA-N 1-(3-butylphenoxy)-4-phenylphthalazine Chemical compound CCCCC1=CC=CC(OC=2C3=CC=CC=C3C(C=3C=CC=CC=3)=NN=2)=C1 MMBCCBHIMLNMOI-UHFFFAOYSA-N 0.000 description 2
- OIIDCQKFULERQS-UHFFFAOYSA-N 1-(3-chloro-4-methylphenoxy)-4-phenylphthalazine Chemical compound Cc1ccc(Oc2nnc(-c3ccccc3)c3ccccc23)cc1Cl OIIDCQKFULERQS-UHFFFAOYSA-N 0.000 description 2
- QVKSDSNZMRSGNE-UHFFFAOYSA-N 1-(3-chlorophenoxy)-4-phenylphthalazine Chemical compound ClC1=CC=CC(OC=2C3=CC=CC=C3C(C=3C=CC=CC=3)=NN=2)=C1 QVKSDSNZMRSGNE-UHFFFAOYSA-N 0.000 description 2
- KQNMQWSQPCROIE-UHFFFAOYSA-N 1-(3-fluoro-4-methylphenoxy)-4-phenylphthalazine Chemical compound Cc1ccc(Oc2nnc(-c3ccccc3)c3ccccc23)cc1F KQNMQWSQPCROIE-UHFFFAOYSA-N 0.000 description 2
- ZZZQQEAIFDZMJL-UHFFFAOYSA-N 1-(3-fluorophenoxy)-4-phenylphthalazine Chemical compound FC1=CC=CC(OC=2C3=CC=CC=C3C(C=3C=CC=CC=3)=NN=2)=C1 ZZZQQEAIFDZMJL-UHFFFAOYSA-N 0.000 description 2
- MLQLEGJPAPMIAW-UHFFFAOYSA-N 1-(3-methoxyphenoxy)-4-phenylphthalazine Chemical compound COC1=CC=CC(OC=2C3=CC=CC=C3C(C=3C=CC=CC=3)=NN=2)=C1 MLQLEGJPAPMIAW-UHFFFAOYSA-N 0.000 description 2
- ZRNCXLJPTVVIOX-UHFFFAOYSA-N 1-(3-methylphenoxy)-4-phenylphthalazine Chemical compound CC1=CC=CC(OC=2C3=CC=CC=C3C(C=3C=CC=CC=3)=NN=2)=C1 ZRNCXLJPTVVIOX-UHFFFAOYSA-N 0.000 description 2
- CXHLEBQTMXEKNP-UHFFFAOYSA-N 1-(4-bromophenoxy)-4-phenylphthalazine Chemical compound C1=CC(Br)=CC=C1OC(C1=CC=CC=C11)=NN=C1C1=CC=CC=C1 CXHLEBQTMXEKNP-UHFFFAOYSA-N 0.000 description 2
- FKKRFXAFQLSVQW-UHFFFAOYSA-N 1-(4-butylphenoxy)-4-phenylphthalazine Chemical compound C1=CC(CCCC)=CC=C1OC(C1=CC=CC=C11)=NN=C1C1=CC=CC=C1 FKKRFXAFQLSVQW-UHFFFAOYSA-N 0.000 description 2
- GDOUMGMIUYAYEG-UHFFFAOYSA-N 1-(4-chloro-2-methoxyphenoxy)-4-phenylphthalazine Chemical compound COc1cc(Cl)ccc1Oc1nnc(-c2ccccc2)c2ccccc12 GDOUMGMIUYAYEG-UHFFFAOYSA-N 0.000 description 2
- IHLUZEFCMPAJFV-UHFFFAOYSA-N 1-(4-chloro-3-methylphenoxy)-4-phenylphthalazine Chemical compound Cc1cc(Oc2nnc(-c3ccccc3)c3ccccc23)ccc1Cl IHLUZEFCMPAJFV-UHFFFAOYSA-N 0.000 description 2
- PLNNDWSJRGHNKF-UHFFFAOYSA-N 1-(4-chlorophenoxy)-4-phenylphthalazine Chemical compound C1=CC(Cl)=CC=C1OC(C1=CC=CC=C11)=NN=C1C1=CC=CC=C1 PLNNDWSJRGHNKF-UHFFFAOYSA-N 0.000 description 2
- FHUUUCAUXGWXRX-UHFFFAOYSA-N 1-(4-ethylphenoxy)-4-phenylphthalazine Chemical compound C1=CC(CC)=CC=C1OC(C1=CC=CC=C11)=NN=C1C1=CC=CC=C1 FHUUUCAUXGWXRX-UHFFFAOYSA-N 0.000 description 2
- SDFDHZJYVFXTPW-UHFFFAOYSA-N 1-(4-fluorophenoxy)-4-phenylphthalazine Chemical compound C1=CC(F)=CC=C1OC(C1=CC=CC=C11)=NN=C1C1=CC=CC=C1 SDFDHZJYVFXTPW-UHFFFAOYSA-N 0.000 description 2
- ZOBPXBWFLDRTPE-UHFFFAOYSA-N 1-(4-methoxyphenoxy)-4-phenylphthalazine Chemical compound C1=CC(OC)=CC=C1OC(C1=CC=CC=C11)=NN=C1C1=CC=CC=C1 ZOBPXBWFLDRTPE-UHFFFAOYSA-N 0.000 description 2
- NMQQXMBZDOOJDH-UHFFFAOYSA-N 1-(4-methylphenoxy)-4-phenylphthalazine Chemical compound C1=CC(C)=CC=C1OC(C1=CC=CC=C11)=NN=C1C1=CC=CC=C1 NMQQXMBZDOOJDH-UHFFFAOYSA-N 0.000 description 2
- BVAZYGMDXRXDTJ-UHFFFAOYSA-N 1-(4-tert-butylphenoxy)-4-phenylphthalazine Chemical compound C1=CC(C(C)(C)C)=CC=C1OC(C1=CC=CC=C11)=NN=C1C1=CC=CC=C1 BVAZYGMDXRXDTJ-UHFFFAOYSA-N 0.000 description 2
- KUZXRBPVTGBFLV-UHFFFAOYSA-N 1-[2-methyl-4-(trifluoromethyl)phenoxy]-4-phenylphthalazine Chemical compound Cc1cc(ccc1Oc1nnc(-c2ccccc2)c2ccccc12)C(F)(F)F KUZXRBPVTGBFLV-UHFFFAOYSA-N 0.000 description 2
- HBOUYHAOPPRVCU-UHFFFAOYSA-N 1-[4-(4-phenylphthalazin-1-yl)oxyphenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1OC(C1=CC=CC=C11)=NN=C1C1=CC=CC=C1 HBOUYHAOPPRVCU-UHFFFAOYSA-N 0.000 description 2
- ZSBMYVJJLUUBKA-UHFFFAOYSA-N 1-[4-[(4-phenylphthalazin-1-yl)amino]phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1NC(C1=CC=CC=C11)=NN=C1C1=CC=CC=C1 ZSBMYVJJLUUBKA-UHFFFAOYSA-N 0.000 description 2
- VNMFPZOFFCNRGY-UHFFFAOYSA-N 1-phenyl-4-(3-propoxyphenoxy)phthalazine Chemical compound CCCOC1=CC=CC(OC=2C3=CC=CC=C3C(C=3C=CC=CC=3)=NN=2)=C1 VNMFPZOFFCNRGY-UHFFFAOYSA-N 0.000 description 2
- VAKBICSGFMGSBO-UHFFFAOYSA-N 1-phenyl-4-[3-(trifluoromethyl)phenoxy]phthalazine Chemical compound FC(F)(F)C1=CC=CC(OC=2C3=CC=CC=C3C(C=3C=CC=CC=3)=NN=2)=C1 VAKBICSGFMGSBO-UHFFFAOYSA-N 0.000 description 2
- DGYHSCMCBBHYSW-UHFFFAOYSA-N 1-phenyl-4-[4-(trifluoromethyl)phenoxy]phthalazine Chemical compound FC(F)(F)c1ccc(Oc2nnc(-c3ccccc3)c3ccccc23)cc1 DGYHSCMCBBHYSW-UHFFFAOYSA-N 0.000 description 2
- ACYPLCVGFPLDQY-UHFFFAOYSA-N 3-(4-phenylphthalazin-1-yl)oxyphenol Chemical compound OC1=CC=CC(OC=2C3=CC=CC=C3C(C=3C=CC=CC=3)=NN=2)=C1 ACYPLCVGFPLDQY-UHFFFAOYSA-N 0.000 description 2
- HUGUFYQVWIPSBE-UHFFFAOYSA-N 3-[(4-phenylphthalazin-1-yl)amino]phenol Chemical compound OC1=CC=CC(NC=2C3=CC=CC=C3C(C=3C=CC=CC=3)=NN=2)=C1 HUGUFYQVWIPSBE-UHFFFAOYSA-N 0.000 description 2
- DLMXLUFVYVOLOC-UHFFFAOYSA-N 4-(4-phenylphthalazin-1-yl)oxybenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OC(C1=CC=CC=C11)=NN=C1C1=CC=CC=C1 DLMXLUFVYVOLOC-UHFFFAOYSA-N 0.000 description 2
- QUWWOEGYJCSXMX-UHFFFAOYSA-N 4-[(4-phenylphthalazin-1-yl)amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(C1=CC=CC=C11)=NN=C1C1=CC=CC=C1 QUWWOEGYJCSXMX-UHFFFAOYSA-N 0.000 description 2
- QQBQYLIRZPWUNC-UHFFFAOYSA-N 4-[(4-phenylphthalazin-1-yl)amino]benzonitrile Chemical compound C1=CC(C#N)=CC=C1NC(C1=CC=CC=C11)=NN=C1C1=CC=CC=C1 QQBQYLIRZPWUNC-UHFFFAOYSA-N 0.000 description 2
- XCPBIZQYJAYOQZ-UHFFFAOYSA-N 4-phenyl-N-(2,4,6-trimethylphenyl)phthalazin-1-amine Chemical compound Cc1cc(C)c(Nc2nnc(-c3ccccc3)c3ccccc23)c(C)c1 XCPBIZQYJAYOQZ-UHFFFAOYSA-N 0.000 description 2
- SCRIQDJLKMSGIG-UHFFFAOYSA-N 4-phenyl-N-(3,4,5-trimethoxyphenyl)phthalazin-1-amine Chemical compound COc1cc(Nc2nnc(-c3ccccc3)c3ccccc23)cc(OC)c1OC SCRIQDJLKMSGIG-UHFFFAOYSA-N 0.000 description 2
- MBXGTKMFGHWQQK-UHFFFAOYSA-N 4-phenyl-N-[2-(trifluoromethyl)phenyl]phthalazin-1-amine Chemical compound FC(F)(F)c1ccccc1Nc1nnc(-c2ccccc2)c2ccccc12 MBXGTKMFGHWQQK-UHFFFAOYSA-N 0.000 description 2
- WCXHPHAFYNVZQB-UHFFFAOYSA-N 4-phenyl-N-[4-(trifluoromethyl)phenyl]phthalazin-1-amine Chemical compound FC(F)(F)c1ccc(Nc2nnc(-c3ccccc3)c3ccccc23)cc1 WCXHPHAFYNVZQB-UHFFFAOYSA-N 0.000 description 2
- MMPMZTYQPIDJFE-UHFFFAOYSA-N 4-phenyl-n-(3-propoxyphenyl)phthalazin-1-amine Chemical compound CCCOC1=CC=CC(NC=2C3=CC=CC=C3C(C=3C=CC=CC=3)=NN=2)=C1 MMPMZTYQPIDJFE-UHFFFAOYSA-N 0.000 description 2
- KNYVGNRPDDBAIP-UHFFFAOYSA-N 4-phenyl-n-[3-(trifluoromethyl)phenyl]phthalazin-1-amine Chemical compound FC(F)(F)C1=CC=CC(NC=2C3=CC=CC=C3C(C=3C=CC=CC=3)=NN=2)=C1 KNYVGNRPDDBAIP-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- YWSLEWNOZWXQQN-UHFFFAOYSA-N C1=CC=C(C=C1)C2=NN=C(C3=CC=CC=C32)OC4=CC(=CC=C4)I Chemical compound C1=CC=C(C=C1)C2=NN=C(C3=CC=CC=C32)OC4=CC(=CC=C4)I YWSLEWNOZWXQQN-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NYTZTBXNGPXPDU-UHFFFAOYSA-N N-(3-chloro-2-methylphenyl)-4-phenylphthalazin-1-amine Chemical compound Cc1c(Cl)cccc1Nc1nnc(-c2ccccc2)c2ccccc12 NYTZTBXNGPXPDU-UHFFFAOYSA-N 0.000 description 2
- CEHQLKSLMFIHBF-UHFFFAOYSA-N N-(3-chlorophenyl)-4-phenyl-1-phthalazinamine Chemical compound ClC1=CC=CC(NC=2C3=CC=CC=C3C(C=3C=CC=CC=3)=NN=2)=C1 CEHQLKSLMFIHBF-UHFFFAOYSA-N 0.000 description 2
- OQGZORZDENPRGX-UHFFFAOYSA-N N-(3-fluoro-4-methylphenyl)-4-phenylphthalazin-1-amine Chemical compound Cc1ccc(Nc2nnc(-c3ccccc3)c3ccccc23)cc1F OQGZORZDENPRGX-UHFFFAOYSA-N 0.000 description 2
- APSAQONFMSJDED-UHFFFAOYSA-N N-(4-chloro-3-methylphenyl)-4-phenylphthalazin-1-amine Chemical compound Cc1cc(Nc2nnc(-c3ccccc3)c3ccccc23)ccc1Cl APSAQONFMSJDED-UHFFFAOYSA-N 0.000 description 2
- LFXHJPHQSQODTB-UHFFFAOYSA-N N-[2-methoxy-5-(trifluoromethyl)phenyl]-4-phenylphthalazin-1-amine Chemical compound COC1=C(NC2=NN=C(C3=CC=CC=C23)C2=CC=CC=C2)C=C(C=C1)C(F)(F)F LFXHJPHQSQODTB-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- HDVONPFBZBEUCH-UHFFFAOYSA-N ethyl 4-(4-phenylphthalazin-1-yl)oxybenzoate Chemical compound CCOC(=O)c1ccc(Oc2nnc(-c3ccccc3)c3ccccc23)cc1 HDVONPFBZBEUCH-UHFFFAOYSA-N 0.000 description 2
- DENHKCMZPFZGQV-UHFFFAOYSA-N ethyl 4-[(4-phenylphthalazin-1-yl)amino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(C1=CC=CC=C11)=NN=C1C1=CC=CC=C1 DENHKCMZPFZGQV-UHFFFAOYSA-N 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
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Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13043479A JPS5653660A (en) | 1979-10-09 | 1979-10-09 | 4-phenylphthalazine derivative |
| GB8030906A GB2063249A (en) | 1979-10-09 | 1980-09-25 | 4-Phenylphthalazine derivatives |
| NL8005411A NL8005411A (nl) | 1979-10-09 | 1980-09-30 | 4-fenylftalazinederivaten. |
| FR8021530A FR2468593A1 (fr) | 1979-10-09 | 1980-10-08 | Derives de 4-phenylphtalazine utilisables comme medicaments inhibiteurs de l'agregation de plaquettes sanguines, et procede pour leur preparation |
| IT25206/80A IT1148727B (it) | 1979-10-09 | 1980-10-08 | Derivati di 4-fenil-ftalazine ad azione terapeutica |
| DE19803038166 DE3038166A1 (de) | 1979-10-09 | 1980-10-09 | 4-phenylphthalazinderivate und verfahren zu deren herstellung, sowie arzneimittel, welche diese enthalten |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13043479A JPS5653660A (en) | 1979-10-09 | 1979-10-09 | 4-phenylphthalazine derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5653660A JPS5653660A (en) | 1981-05-13 |
| JPS6242901B2 true JPS6242901B2 (enrdf_load_stackoverflow) | 1987-09-10 |
Family
ID=15034137
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13043479A Granted JPS5653660A (en) | 1979-10-09 | 1979-10-09 | 4-phenylphthalazine derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5653660A (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW279162B (enrdf_load_stackoverflow) * | 1991-09-26 | 1996-06-21 | Mitsubishi Chem Corp | |
| ATE157871T1 (de) | 1994-05-19 | 1997-09-15 | Mitsubishi Chem Corp | Arzneimittel zur therapeutischen und prophylaktischen behandlung von krankheiten, die durch hyperplasie der glatten muskelzellen bedingt sind |
-
1979
- 1979-10-09 JP JP13043479A patent/JPS5653660A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5653660A (en) | 1981-05-13 |
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