JPH0358343B2 - - Google Patents

Info

Publication number: JPH0358343B2
Authority: JP; Japan
Prior art keywords: methoxyphenyl; ethyl; piperazinyl; quinazolinedione; solvent
Prior art date: 1983-04-08
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

Application number

JP6092883A

Other languages

English (en)

Japanese (ja)

Other versions

JPS59186963A (ja

Inventor

Noboru Kubodera

Hiroyuki Nagano

Tomohiko Fukatsu

Michiro Takagi

Isao Matsunaga

Hiroyuki Nahata

Yasuhiro Ooba

Kazunari Sakai

Shunichi Hata

Yasuyoshi Uchida

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Chugai Pharmaceutical Co Ltd

Original Assignee

Chugai Pharmaceutical Co Ltd

Priority date (The priority date 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 date listed.)

1983-04-08

Filing date

1983-04-08

Publication date

1991-09-05

1983-04-08 Application filed by Chugai Pharmaceutical Co Ltd filed Critical Chugai Pharmaceutical Co Ltd

1983-04-08 Priority to JP6092883A priority Critical patent/JPS59186963A/ja

1984-10-23 Publication of JPS59186963A publication Critical patent/JPS59186963A/ja

1991-09-05 Publication of JPH0358343B2 publication Critical patent/JPH0358343B2/ja

Status Granted legal-status Critical Current

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

JP6092883A 1983-04-08 1983-04-08 新規なフエニルピペラジン誘導体 Granted JPS59186963A (ja)

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 (hu)	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 (hu)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
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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JP2667987B2 (ja)	1997-10-27	５−［２−（４−（ベンゾイソチアゾール−３−イル）−ピペラジン−１−イル）エチル］−６−クロロ−１，３−ジヒドロ−インドール−２−オンの製造方法及び製造用中間体
PL161379B1 (pl)	1993-06-30	S p o só b wytwarzania kwasu 2-[2-[4-[/4-chlorofenylo/fenylom etylo]-1-piperazynylo] etoksy]octow ego i jego dichlorowodorku PL PL
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