JPH0358343B2 - - Google Patents
Info
- Publication number
- JPH0358343B2 JPH0358343B2 JP6092883A JP6092883A JPH0358343B2 JP H0358343 B2 JPH0358343 B2 JP H0358343B2 JP 6092883 A JP6092883 A JP 6092883A JP 6092883 A JP6092883 A JP 6092883A JP H0358343 B2 JPH0358343 B2 JP H0358343B2
- Authority
- JP
- Japan
- Prior art keywords
- methoxyphenyl
- ethyl
- piperazinyl
- quinazolinedione
- solvent
- 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
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical class C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 17
- 238000000921 elemental analysis Methods 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000002844 melting Methods 0.000 description 15
- 230000008018 melting Effects 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- SDQJTWBNWQABLE-UHFFFAOYSA-N 1h-quinazoline-2,4-dione Chemical compound C1=CC=C2C(=O)NC(=O)NC2=C1 SDQJTWBNWQABLE-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- GCFHZZWXZLABBL-UHFFFAOYSA-N ethanol;hexane Chemical compound CCO.CCCCCC GCFHZZWXZLABBL-UHFFFAOYSA-N 0.000 description 5
- -1 sodium borohydride Chemical class 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- ZFDWAPWETDMDSZ-UHFFFAOYSA-N 3-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-1h-quinazoline-2,4-dione Chemical compound COC1=CC=CC=C1N1CCN(CCN2C(C3=CC=CC=C3NC2=O)=O)CC1 ZFDWAPWETDMDSZ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-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
- 238000001816 cooling Methods 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 235000009518 sodium iodide Nutrition 0.000 description 3
- VNZLQLYBRIOLFZ-UHFFFAOYSA-N 1-(2-methoxyphenyl)piperazine Chemical compound COC1=CC=CC=C1N1CCNCC1 VNZLQLYBRIOLFZ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000004423 acyloxy group Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000003936 benzamides Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- ZTUDBKOGHVEHPH-UHFFFAOYSA-N 1-(5-hydroxypentyl)-3-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]quinazoline-2,4-dione Chemical compound COC1=CC=CC=C1N1CCN(CCN2C(C3=CC=CC=C3N(CCCCCO)C2=O)=O)CC1 ZTUDBKOGHVEHPH-UHFFFAOYSA-N 0.000 description 1
- WEPMEULXRILNGE-UHFFFAOYSA-N 1-heptyl-3-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]quinazoline-2,4-dione;dihydrochloride Chemical compound Cl.Cl.O=C1N(CCCCCCC)C2=CC=CC=C2C(=O)N1CCN(CC1)CCN1C1=CC=CC=C1OC WEPMEULXRILNGE-UHFFFAOYSA-N 0.000 description 1
- XINHGNQNSGGLQW-UHFFFAOYSA-N 1h-quinazoline-2,4-dione;dihydrochloride Chemical compound Cl.Cl.C1=CC=C2C(=O)NC(=O)NC2=C1 XINHGNQNSGGLQW-UHFFFAOYSA-N 0.000 description 1
- LUQFTTCSOIWEPL-UHFFFAOYSA-N 1h-quinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1=CC=C2C(=O)NC(=O)NC2=C1 LUQFTTCSOIWEPL-UHFFFAOYSA-N 0.000 description 1
- IJFYTFNYIQWTSR-UHFFFAOYSA-N 2-amino-4-chloro-n-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-5-sulfamoylbenzamide Chemical compound COC1=CC=CC=C1N1CCN(CCNC(=O)C=2C(=CC(Cl)=C(C=2)S(N)(=O)=O)N)CC1 IJFYTFNYIQWTSR-UHFFFAOYSA-N 0.000 description 1
- LZCOBDGUDICOAR-UHFFFAOYSA-N 3-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-1-(5-oxohexyl)quinazoline-2,4-dione Chemical compound COC1=CC=CC=C1N1CCN(CCN2C(C3=CC=CC=C3N(CCCCC(C)=O)C2=O)=O)CC1 LZCOBDGUDICOAR-UHFFFAOYSA-N 0.000 description 1
- RJQLKYIVMDFWRF-FOCLMDBBSA-N 3-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-1-[(e)-3-oxooct-1-enyl]quinazoline-2,4-dione Chemical compound O=C1N(/C=C/C(=O)CCCCC)C2=CC=CC=C2C(=O)N1CCN(CC1)CCN1C1=CC=CC=C1OC RJQLKYIVMDFWRF-FOCLMDBBSA-N 0.000 description 1
- WUULBRQJNBQXNB-UHFFFAOYSA-N 3-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-1-pentylquinazoline-2,4-dione dihydrochloride Chemical compound Cl.Cl.O=C1N(CCCCC)C2=CC=CC=C2C(=O)N1CCN(CC1)CCN1C1=CC=CC=C1OC WUULBRQJNBQXNB-UHFFFAOYSA-N 0.000 description 1
- VMZMBFADCKHMTP-UHFFFAOYSA-N 3-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-1-propan-2-ylquinazoline-2,4-dione;dihydrochloride Chemical compound Cl.Cl.COC1=CC=CC=C1N1CCN(CCN2C(C3=CC=CC=C3N(C(C)C)C2=O)=O)CC1 VMZMBFADCKHMTP-UHFFFAOYSA-N 0.000 description 1
- PITJCAIZBLRLKS-UHFFFAOYSA-N 4-[3-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-2,4-dioxoquinazolin-1-yl]butanoic acid Chemical compound COC1=CC=CC=C1N1CCN(CCN2C(C3=CC=CC=C3N(CCCC(O)=O)C2=O)=O)CC1 PITJCAIZBLRLKS-UHFFFAOYSA-N 0.000 description 1
- OUEKHGIOSDZUOG-UHFFFAOYSA-N 5-[3-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-2,4-dioxoquinazolin-1-yl]pentyl acetate Chemical compound COC1=CC=CC=C1N1CCN(CCN2C(C3=CC=CC=C3N(CCCCCOC(C)=O)C2=O)=O)CC1 OUEKHGIOSDZUOG-UHFFFAOYSA-N 0.000 description 1
- ZCYVIAZIVJNAMO-UHFFFAOYSA-N 5-chloropentyl acetate Chemical compound CC(=O)OCCCCCCl ZCYVIAZIVJNAMO-UHFFFAOYSA-N 0.000 description 1
- OJRUZZLZXHSTAH-UHFFFAOYSA-N 7-chloro-2,4-dioxo-1h-3,1-benzoxazine-6-sulfonamide Chemical compound N1C(=O)OC(=O)C2=C1C=C(Cl)C(S(=O)(=O)N)=C2 OJRUZZLZXHSTAH-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000000794 anti-serotonin Effects 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000003420 antiserotonin agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- PDQSQGXAZOHJOB-UHFFFAOYSA-N ethyl 4-[3-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-2,4-dioxoquinazolin-1-yl]butanoate;dihydrochloride Chemical compound Cl.Cl.O=C1N(CCCC(=O)OCC)C2=CC=CC=C2C(=O)N1CCN(CC1)CCN1C1=CC=CC=C1OC PDQSQGXAZOHJOB-UHFFFAOYSA-N 0.000 description 1
- LAWVACBTMZOBDC-UHFFFAOYSA-N ethyl 5-[3-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-2,4-dioxoquinazolin-1-yl]pentanoate;dihydrochloride Chemical compound Cl.Cl.O=C1N(CCCCC(=O)OCC)C2=CC=CC=C2C(=O)N1CCN(CC1)CCN1C1=CC=CC=C1OC LAWVACBTMZOBDC-UHFFFAOYSA-N 0.000 description 1
- OOBFNDGMAGSNKA-UHFFFAOYSA-N ethyl 7-bromoheptanoate Chemical compound CCOC(=O)CCCCCCBr OOBFNDGMAGSNKA-UHFFFAOYSA-N 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- GGQOPZKTDHXXON-UHFFFAOYSA-N hexane;methanol Chemical compound OC.CCCCCC GGQOPZKTDHXXON-UHFFFAOYSA-N 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 229940097275 indigo Drugs 0.000 description 1
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000000810 peripheral vasodilating agent Substances 0.000 description 1
- 229960002116 peripheral vasodilator Drugs 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 229940124550 renal vasodilator Drugs 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- LMIRGQMBYXMZGJ-UHFFFAOYSA-N trifluoromethyl carbonochloridate Chemical compound FC(F)(F)OC(Cl)=O LMIRGQMBYXMZGJ-UHFFFAOYSA-N 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6092883A JPS59186963A (ja) | 1983-04-08 | 1983-04-08 | 新規なフエニルピペラジン誘導体 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6092883A JPS59186963A (ja) | 1983-04-08 | 1983-04-08 | 新規なフエニルピペラジン誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59186963A JPS59186963A (ja) | 1984-10-23 |
| JPH0358343B2 true JPH0358343B2 (fr) | 1991-09-05 |
Family
ID=13156530
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6092883A Granted JPS59186963A (ja) | 1983-04-08 | 1983-04-08 | 新規なフエニルピペラジン誘導体 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59186963A (fr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60169467A (ja) * | 1984-02-10 | 1985-09-02 | Chugai Pharmaceut Co Ltd | 新規なフエニルピペラジン誘導体 |
| GB8524663D0 (en) * | 1985-10-07 | 1985-11-13 | Fujisawa Pharmaceutical Co | Quinazoline derivatives |
-
1983
- 1983-04-08 JP JP6092883A patent/JPS59186963A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59186963A (ja) | 1984-10-23 |
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