JPS6244525B2 - - Google Patents
Info
- Publication number
- JPS6244525B2 JPS6244525B2 JP13043579A JP13043579A JPS6244525B2 JP S6244525 B2 JPS6244525 B2 JP S6244525B2 JP 13043579 A JP13043579 A JP 13043579A JP 13043579 A JP13043579 A JP 13043579A JP S6244525 B2 JPS6244525 B2 JP S6244525B2
- Authority
- JP
- Japan
- Prior art keywords
- phenylphthalazine
- group
- carbon atoms
- formula
- compound
- 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
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 101000783577 Dendroaspis angusticeps Thrombostatin Proteins 0.000 claims description 6
- 101000783578 Dendroaspis jamesoni kaimosae Dendroaspin Proteins 0.000 claims description 6
- 229940127218 antiplatelet drug Drugs 0.000 claims description 6
- 239000000106 platelet aggregation inhibitor Substances 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- -1 n -butyl Chemical group 0.000 description 50
- 150000001875 compounds Chemical class 0.000 description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 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
- 239000013078 crystal Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- IGUVJKICKDRMPR-UHFFFAOYSA-N n-(4-methylphenyl)-4-phenylphthalazin-1-amine Chemical compound C1=CC(C)=CC=C1NC(C1=CC=CC=C11)=NN=C1C1=CC=CC=C1 IGUVJKICKDRMPR-UHFFFAOYSA-N 0.000 description 5
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 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 4
- KHIILJVSYUGMSE-UHFFFAOYSA-N 1-phenylphthalazine Chemical class C1=CC=CC=C1C1=NN=CC2=CC=CC=C12 KHIILJVSYUGMSE-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- RGQBTUTXCYXHBS-UHFFFAOYSA-N n-(2-methylphenyl)-4-phenylphthalazin-1-amine Chemical compound CC1=CC=CC=C1NC(C1=CC=CC=C11)=NN=C1C1=CC=CC=C1 RGQBTUTXCYXHBS-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- PTGXMBPJFXPBQV-UHFFFAOYSA-N 1-phenoxy-4-phenylphthalazine Chemical compound N=1N=C(C=2C=CC=CC=2)C2=CC=CC=C2C=1OC1=CC=CC=C1 PTGXMBPJFXPBQV-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
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-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
- 239000002253 acid Substances 0.000 description 3
- 239000000969 carrier 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
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- BEATZJALKXTWKH-UHFFFAOYSA-N n,4-diphenylphthalazin-1-amine Chemical compound N=1N=C(C=2C=CC=CC=2)C2=CC=CC=C2C=1NC1=CC=CC=C1 BEATZJALKXTWKH-UHFFFAOYSA-N 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical class SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- 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
- TWIRDKAZASCDRR-UHFFFAOYSA-N 1-(2,5-dimethylphenoxy)-4-phenylphthalazine Chemical compound CC1=CC=C(C)C(OC=2C3=CC=CC=C3C(C=3C=CC=CC=3)=NN=2)=C1 TWIRDKAZASCDRR-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
- 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
- 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
- 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 2
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 2
- 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 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
- 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
- KNJJELJJBCAVFR-UHFFFAOYSA-N 4-(4-phenylphthalazin-1-yl)oxybenzonitrile Chemical compound C1=CC(C#N)=CC=C1OC(C1=CC=CC=C11)=NN=C1C1=CC=CC=C1 KNJJELJJBCAVFR-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
- 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
- 229920002261 Corn starch Polymers 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
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- FNMLHKZMAXXQFU-UHFFFAOYSA-N N-(2-methoxy-5-methylphenyl)-4-phenylphthalazin-1-amine Chemical compound COc1ccc(C)cc1Nc1nnc(-c2ccccc2)c2ccccc12 FNMLHKZMAXXQFU-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
- MGHYQBWVEBFXLH-UHFFFAOYSA-N N-(3-chloro-4-methylphenyl)-4-phenylphthalazin-1-amine Chemical compound Cc1ccc(Nc2nnc(-c3ccccc3)c3ccccc23)cc1Cl MGHYQBWVEBFXLH-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
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- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13043579A JPS5653659A (en) | 1979-10-09 | 1979-10-09 | Blood platelet coagulation suppressing agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13043579A JPS5653659A (en) | 1979-10-09 | 1979-10-09 | Blood platelet coagulation suppressing agent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5653659A JPS5653659A (en) | 1981-05-13 |
| JPS6244525B2 true JPS6244525B2 (enrdf_load_stackoverflow) | 1987-09-21 |
Family
ID=15034159
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13043579A Granted JPS5653659A (en) | 1979-10-09 | 1979-10-09 | Blood platelet coagulation suppressing agent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5653659A (enrdf_load_stackoverflow) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW279162B (enrdf_load_stackoverflow) * | 1991-09-26 | 1996-06-21 | Mitsubishi Chem Corp | |
| DE69500673T2 (de) | 1994-05-19 | 1998-03-19 | Mitsubishi Chem Corp | Arzneimittel zur therapeutischen und prophylaktischen Behandlung von Krankheiten, die durch Hyperplasie der glatten Muskelzellen bedingt sind |
| US5776962A (en) * | 1994-08-03 | 1998-07-07 | Cell Pathways, Inc. | Lactone compounds for treating patient with precancerous lesions |
| US5696159A (en) * | 1994-08-03 | 1997-12-09 | Cell Pathways, Inc. | Lactone compounds for treating patients with precancerous lesions |
| US6060477A (en) * | 1995-06-07 | 2000-05-09 | Cell Pathways, Inc. | Method of treating a patient having precancerous lesions with phenyl cycloamino pyrimidinone derivatives |
| US6232312B1 (en) | 1995-06-07 | 2001-05-15 | Cell Pathways, Inc. | Method for treating patient having precancerous lesions with a combination of pyrimidopyrimidine derivatives and esters and amides of substituted indenyl acetic acides |
| US5874440A (en) * | 1995-06-07 | 1999-02-23 | Cell Pathways, Inc. | Method of treating a patient having precancerous lesions with phenyl pyrimidinone derivatives |
| US6046216A (en) * | 1995-06-07 | 2000-04-04 | Cell Pathways, Inc. | Method of treating a patient having precancerous lesions with phenyl pyridinone derivatives |
| US6262059B1 (en) | 1995-06-07 | 2001-07-17 | Cell Pathways, Inc. | Method of treating a patient having precancerous lesions with quinazoline derivatives |
| US6046206A (en) * | 1995-06-07 | 2000-04-04 | Cell Pathways, Inc. | Method of treating a patient having a precancerous lesions with amide quinazoline derivatives |
| CA2238283C (en) | 1997-05-30 | 2002-08-20 | Cell Pathways, Inc. | Method for identifying compounds for inhibition of neoplastic lesions, pharmaceutical compositions from such compounds and uses of such compounds and compositions for treating neoplastic lesions |
| US5858694A (en) * | 1997-05-30 | 1999-01-12 | Cell Pathways, Inc. | Method for identifying compounds for inhibition of cancerous lesions |
| US5852035A (en) * | 1997-12-12 | 1998-12-22 | Cell Pathways, Inc. | Method for inhibiting neoplastic cells and related conditions by exposure to substituted N- arylmethyl and heterocyclmethyl-1H-pyrazolo (3,4-B) quinolin-4-amines |
| US6046199A (en) * | 1998-01-14 | 2000-04-04 | Cell Pathways, Inc. | Method of inhibiting neoplastic cells with tetracyclic pyrido[3,4-B]indole derivatives |
| US6410584B1 (en) | 1998-01-14 | 2002-06-25 | Cell Pathways, Inc. | Method for inhibiting neoplastic cells with indole derivatives |
| US5942520A (en) * | 1998-01-27 | 1999-08-24 | Cell Pathways, Inc. | Method for inhibiting neoplastic cells by exposure to substituted N-cycloalkylmethyl-1-H-pyrazolo (3,4-B) quinolone-4 amines |
| US5990117A (en) * | 1998-04-15 | 1999-11-23 | Cell Pathways, Inc. | Method for inhibiting neoplastic cells and related conditions by exposure to quinazoline derivatives |
| US6124303A (en) * | 1998-09-11 | 2000-09-26 | Cell Pathways, Inc. | Method for inhibiting neoplastic cells and related conditions by exposure to 9-substituted 2-(2-N-aloxyphenyl) purin-6-ones |
| US6268372B1 (en) | 1998-09-11 | 2001-07-31 | Cell Pathways, Inc. | Method for inhibiting neoplastic cells and related conditions by exposure to 2,9-disubstituted purin-6-ones |
| US6130053A (en) * | 1999-08-03 | 2000-10-10 | Cell Pathways, Inc. | Method for selecting compounds for inhibition of neoplastic lesions |
| US6200771B1 (en) | 1998-10-15 | 2001-03-13 | Cell Pathways, Inc. | Method of using a novel phosphodiesterase in pharmaceutical screeing to identify compounds for treatment of neoplasia |
| US6133271A (en) * | 1998-11-19 | 2000-10-17 | Cell Pathways, Inc. | Method for inhibiting neoplastic cells and related conditions by exposure thienopyrimidine derivatives |
| US6187779B1 (en) | 1998-11-20 | 2001-02-13 | Cell Pathways, Inc. | Method for inhibiting neoplastic cells and related conditions by exposure to 2,8-disubstituted quinazoline derivatives |
| US6369092B1 (en) | 1998-11-23 | 2002-04-09 | Cell Pathways, Inc. | Method for treating neoplasia by exposure to substituted benzimidazole derivatives |
| US6034099A (en) * | 1998-11-24 | 2000-03-07 | Cell Pathways, Inc. | Method for inhibiting neoplastic lesions by administering 4-(arylmethylene)- 2, 3- dihydro-pyrazol-3-ones |
| US6486155B1 (en) | 1998-11-24 | 2002-11-26 | Cell Pathways Inc | Method of inhibiting neoplastic cells with isoquinoline derivatives |
| US6077842A (en) * | 1998-11-24 | 2000-06-20 | Cell Pathways, Inc. | Method of inhibiting neoplastic cells with pyrazolopyridylpyridazinone derivatives |
| US6020379A (en) * | 1999-02-19 | 2000-02-01 | Cell Pathways, Inc. | Position 7 substituted indenyl-3-acetic acid derivatives and amides thereof for the treatment of neoplasia |
| US6555547B1 (en) | 2000-02-28 | 2003-04-29 | Cell Pathways, Inc. | Method for treating a patient with neoplasia by treatment with a vinca alkaloid derivative |
| US6569638B1 (en) | 2000-03-03 | 2003-05-27 | Cell Pathways, Inc | Method for screening compounds for the treatment of neoplasia |
-
1979
- 1979-10-09 JP JP13043579A patent/JPS5653659A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5653659A (en) | 1981-05-13 |
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