JPH0160027B2 - - Google Patents

Info

Publication number: JPH0160027B2
Authority: JP; Japan
Prior art keywords: methyl; oxadiazole; spectrum; nitrosamino; morpholino
Prior art date: 1981-06-04
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

JP8500081A

Other languages

English (en)

Japanese (ja)

Other versions

JPS57200372A (en

Inventor

Hiroyoshi Hidaka

Masatoshi Ban

Yasuaki Kondo

Tomoo Suzuki

Eiichi Suenaga

Akiji Kuwayama

Hiromoto Asai

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.)

Sanwa Kagaku Kenkyusho Co Ltd

Original Assignee

Sanwa Kagaku Kenkyusho 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.)

1981-06-04

Filing date

1981-06-04

Publication date

1989-12-20

1981-06-04 Application filed by Sanwa Kagaku Kenkyusho Co Ltd filed Critical Sanwa Kagaku Kenkyusho Co Ltd

1981-06-04 Priority to JP8500081A priority Critical patent/JPS57200372A/ja

1982-12-08 Publication of JPS57200372A publication Critical patent/JPS57200372A/ja

1989-12-20 Publication of JPH0160027B2 publication Critical patent/JPH0160027B2/ja

Status Granted legal-status Critical Current

Links

VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical class N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 claims description 3
239000003146 anticoagulant agent Substances 0.000 claims description 3
229960004676 antithrombotic agent Drugs 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
239000002075 main ingredient Substances 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
-1 5-substituted-2-[(N-morpholinoamino)-methyl]oxadiazole Chemical class 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
238000002329 infrared spectrum Methods 0.000 description 12
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 12
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 12
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 12
239000000203 mixture Substances 0.000 description 11
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
239000000741 silica gel Substances 0.000 description 10
229910002027 silica gel Inorganic materials 0.000 description 10
150000001875 compounds Chemical class 0.000 description 8
238000004519 manufacturing process Methods 0.000 description 8
239000000126 substance Substances 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
238000000921 elemental analysis Methods 0.000 description 6
238000001819 mass spectrum Methods 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
MKQLBNJQQZRQJU-UHFFFAOYSA-N morpholin-4-amine Chemical compound NN1CCOCC1 MKQLBNJQQZRQJU-UHFFFAOYSA-N 0.000 description 6
125000000018 nitroso group Chemical group N(=O)* 0.000 description 6
WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
235000010288 sodium nitrite Nutrition 0.000 description 6
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
238000001816 cooling Methods 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
239000003814 drug Substances 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
229940079593 drug Drugs 0.000 description 3
210000004623 platelet-rich plasma Anatomy 0.000 description 3
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 2
238000011047 acute toxicity test Methods 0.000 description 2
238000004220 aggregation Methods 0.000 description 2
230000002776 aggregation Effects 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
239000008280 blood Substances 0.000 description 2
210000004204 blood vessel Anatomy 0.000 description 2
210000002808 connective tissue Anatomy 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
238000000034 method Methods 0.000 description 2
XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 2
239000002504 physiological saline solution Substances 0.000 description 2
239000012488 sample solution Substances 0.000 description 2
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
239000000243 solution Substances 0.000 description 2
208000010110 spontaneous platelet aggregation Diseases 0.000 description 2
238000003756 stirring Methods 0.000 description 2
230000002792 vascular Effects 0.000 description 2
UCGJAQHFSXERIT-UHFFFAOYSA-N 2-(chloromethyl)-5-propan-2-yl-1,3,4-oxadiazole Chemical compound CC(C)C1=NN=C(CCl)O1 UCGJAQHFSXERIT-UHFFFAOYSA-N 0.000 description 1
WNHVLRSXJZLWNT-UHFFFAOYSA-N 2-(chloromethyl)-5-propyl-1,3,4-oxadiazole Chemical compound CCCC1=NN=C(CCl)O1 WNHVLRSXJZLWNT-UHFFFAOYSA-N 0.000 description 1
229930008281 A03AD01 - Papaverine Natural products 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
241000978776 Senegalia senegal Species 0.000 description 1
208000007536 Thrombosis Diseases 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
230000002785 anti-thrombosis Effects 0.000 description 1
210000000709 aorta Anatomy 0.000 description 1
210000001841 basilar artery Anatomy 0.000 description 1
210000001772 blood platelet Anatomy 0.000 description 1
230000037396 body weight Effects 0.000 description 1
210000002449 bone cell Anatomy 0.000 description 1
238000009395 breeding Methods 0.000 description 1
230000001488 breeding effect Effects 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
230000008602 contraction Effects 0.000 description 1
210000004351 coronary vessel Anatomy 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000005520 cutting process Methods 0.000 description 1
238000007865 diluting Methods 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
230000009982 effect on human Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229960001340 histamine Drugs 0.000 description 1
230000001939 inductive effect Effects 0.000 description 1
210000001363 mesenteric artery superior Anatomy 0.000 description 1
XLFWDASMENKTKL-UHFFFAOYSA-N molsidomine Chemical compound O1C(N=C([O-])OCC)=C[N+](N2CCOCC2)=N1 XLFWDASMENKTKL-UHFFFAOYSA-N 0.000 description 1
229960004027 molsidomine Drugs 0.000 description 1
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
210000002464 muscle smooth vascular Anatomy 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
229960001789 papaverine Drugs 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
210000002254 renal artery Anatomy 0.000 description 1
229940076279 serotonin Drugs 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
238000002834 transmittance Methods 0.000 description 1
HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
229940038773 trisodium citrate Drugs 0.000 description 1

Landscapes

Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

JP8500081A 1981-06-04 1981-06-04 Novel 5-substituted-2-((n-morpholino)-n-nitrosoamino- methyl)oxadiazole derivative and preventing agent for thrombosis containing the same as principal constituent Granted JPS57200372A (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP8500081A JPS57200372A (en)	1981-06-04	1981-06-04	Novel 5-substituted-2-((n-morpholino)-n-nitrosoamino- methyl)oxadiazole derivative and preventing agent for thrombosis containing the same as principal constituent

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP8500081A JPS57200372A (en)	1981-06-04	1981-06-04	Novel 5-substituted-2-((n-morpholino)-n-nitrosoamino- methyl)oxadiazole derivative and preventing agent for thrombosis containing the same as principal constituent

Publications (2)

Publication Number	Publication Date
JPS57200372A JPS57200372A (en)	1982-12-08
JPH0160027B2 true JPH0160027B2 (fr)	1989-12-20

Family

ID=13846370

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP8500081A Granted JPS57200372A (en)	1981-06-04	1981-06-04	Novel 5-substituted-2-((n-morpholino)-n-nitrosoamino- methyl)oxadiazole derivative and preventing agent for thrombosis containing the same as principal constituent

Country Status (1)

Country	Link
JP (1)	JPS57200372A (fr)

1981
- 1981-06-04 JP JP8500081A patent/JPS57200372A/ja active Granted

Also Published As

Publication number	Publication date
JPS57200372A (en)	1982-12-08

Publication	Publication Date	Title
US4879301A (en)	1989-11-07	Antiallergic and antiinflammatory benzothiazolinone derivatives
JPS61236778A (ja)	1986-10-22	５−置換ピラゾロ〔４，３−ｄ〕ピリミジン−７−オン
FR2513250A1 (fr)	1983-03-25	Nouvelles cyclobutene-3,4-diones substituees
JPS6310154B2 (fr)	1988-03-04
SE457083B (sv)	1988-11-28	1-substituerad teobromin, saett att framstaella denna och en farmaceutisk komposition
JPS606685A (ja)	1985-01-14	カルボスチリル誘導体
JPS6322082A (ja)	1988-01-29	１―（ヒドロキシスチリル）―５ｈ―２，３―ベンゾジアゼピン誘導体およびその製造方法、並びに前記誘導体を含む薬剤
CH663207A5 (fr)	1987-11-30	Derives de l'oxazolidine-1-3 one-2 et procedes pour leur preparation.
JPH0160027B2 (fr)	1989-12-20
CS196333B2 (en)	1980-03-31	Method of producing/alpha-aminoacetyl/benzene derivatives
SU1097195A3 (ru)	1984-06-07	Способ получени производных 2-аминокарбонилоксиалкил-1,4-дигидропиридина
HU193065B (en)	1987-08-28	Process for preparing 6-/2-/4-/1h-imidazol-1-yl/-phenyl/-alkyl- or -alkenyl/-3/2h/-pyridazinone derivatives and pharmaceutical compositions containing thereof
US4430342A (en)	1984-02-07	N-Acyl-3-[4-(benzoylalkyl)piperazin-1-yl]-sydnonimine compound, process for prodction thereof, and use thereof
SU1722227A3 (ru)	1992-03-23	Способ получени производных 1-ацил-2,3-дигидро-4(IH)-хинолинон-4-оксима или их солей
JPS62281860A (ja)	1987-12-07	アルキレンアミノアルキレン　ヘテロ原子基を有するジヒドロ−３，５−ジカルボキシレ−ト
SE466104B (sv)	1991-12-16	Nya triazolpyrimidiner och foerfarande foer deras framstaellning
JPH0545585B2 (fr)	1993-07-09
EP0007648B1 (fr)	1982-08-11	Acylurées à activité pharmaceutique, procédé pour leur préparation, et compositions pharmaceutiques les contenant
SU1590041A3 (ru)	1990-08-30	Способ получени производных 1,4-дигидропиридина
JP2001501627A (ja)	2001-02-06	新規ペンタエリスリトール誘導体、その製造方法および使用ならびにその合成のための中間体
JPH0222069B2 (fr)	1990-05-17
US4500708A (en)	1985-02-19	Benzothiazine derivatives
JPS6383088A (ja)	1988-04-13	ベンゾピラノピラゾレン誘導体
FR2502619A1 (fr)	1982-10-01	Derives de la 1(2h)-isoquinolone et leurs utilisations therapeutiques notamment dans le traitement des ulceres
KR850000210B1 (ko)	1985-03-06	옥사졸린의 제조방법