JPH0222069B2 - - Google Patents

Info

Publication number: JPH0222069B2
Authority: JP; Japan
Prior art keywords: methyl; spectrum; tetrazole; group; chloroform
Prior art date: 1981-07-28
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

JP11718181A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5821670A (ja

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.)

1981-07-28

Filing date

1981-07-28

Publication date

1990-05-17

1981-07-28 Application filed by Sanwa Kagaku Kenkyusho Co Ltd filed Critical Sanwa Kagaku Kenkyusho Co Ltd

1981-07-28 Priority to JP11718181A priority Critical patent/JPS5821670A/ja

1983-02-08 Publication of JPS5821670A publication Critical patent/JPS5821670A/ja

1990-05-17 Publication of JPH0222069B2 publication Critical patent/JPH0222069B2/ja

Status Granted legal-status Critical Current

Links

125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 3
239000003146 anticoagulant agent Substances 0.000 claims description 3
229960004676 antithrombotic agent Drugs 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
239000000203 mixture Substances 0.000 description 20
-1 1-substituted-2-[(N-morpholinoamino)methyl]-tetrazole Chemical class 0.000 description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
230000015572 biosynthetic process Effects 0.000 description 14
238000002329 infrared spectrum Methods 0.000 description 14
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 14
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 14
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 14
238000001228 spectrum Methods 0.000 description 14
238000003786 synthesis reaction Methods 0.000 description 14
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 13
229910052938 sodium sulfate Inorganic materials 0.000 description 13
235000011152 sodium sulphate Nutrition 0.000 description 13
239000013076 target substance Substances 0.000 description 13
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
238000004519 manufacturing process Methods 0.000 description 12
238000000034 method Methods 0.000 description 10
150000001875 compounds Chemical class 0.000 description 9
238000002844 melting Methods 0.000 description 9
230000008018 melting Effects 0.000 description 9
238000001816 cooling Methods 0.000 description 8
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
125000003277 amino group Chemical group 0.000 description 7
235000011114 ammonium hydroxide Nutrition 0.000 description 7
MKQLBNJQQZRQJU-UHFFFAOYSA-N morpholin-4-amine Chemical compound NN1CCOCC1 MKQLBNJQQZRQJU-UHFFFAOYSA-N 0.000 description 7
125000000018 nitroso group Chemical group N(=O)* 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
235000010288 sodium nitrite Nutrition 0.000 description 7
239000000243 solution Substances 0.000 description 7
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
239000003814 drug Substances 0.000 description 4
229940079593 drug Drugs 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
210000004623 platelet-rich plasma Anatomy 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000000126 substance Substances 0.000 description 4
150000003536 tetrazoles Chemical class 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
238000009472 formulation Methods 0.000 description 3
150000002832 nitroso derivatives Chemical class 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
230000007059 acute toxicity Effects 0.000 description 2
231100000403 acute toxicity Toxicity 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
239000012141 concentrate Substances 0.000 description 2
210000002808 connective tissue Anatomy 0.000 description 2
201000010099 disease Diseases 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
239000008187 granular material Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 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
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
208000010110 spontaneous platelet aggregation Diseases 0.000 description 2
238000002834 transmittance Methods 0.000 description 2
SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
NAOJYFAMSKIRIE-UHFFFAOYSA-N 5-(chloromethyl)-1-ethyltetrazole Chemical compound CCN1N=NN=C1CCl NAOJYFAMSKIRIE-UHFFFAOYSA-N 0.000 description 1
QVMQSOGTBSMUQG-UHFFFAOYSA-N 5-(chloromethyl)-1-methyltetrazole Chemical compound CN1N=NN=C1CCl QVMQSOGTBSMUQG-UHFFFAOYSA-N 0.000 description 1
KASHDYDHJFKPQK-UHFFFAOYSA-N 5-(chloromethyl)-1-phenyltetrazole Chemical compound ClCC1=NN=NN1C1=CC=CC=C1 KASHDYDHJFKPQK-UHFFFAOYSA-N 0.000 description 1
XZGLNCKSNVGDNX-UHFFFAOYSA-N 5-methyl-2h-tetrazole Chemical compound CC=1N=NNN=1 XZGLNCKSNVGDNX-UHFFFAOYSA-N 0.000 description 1
229930008281 A03AD01 - Papaverine Natural products 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
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 1
241000283973 Oryctolagus cuniculus 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
239000004480 active ingredient Substances 0.000 description 1
230000002785 anti-thrombosis Effects 0.000 description 1
210000004204 blood vessel Anatomy 0.000 description 1
238000009395 breeding Methods 0.000 description 1
230000001488 breeding effect Effects 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
230000008602 contraction Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
238000005520 cutting process Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000007865 diluting Methods 0.000 description 1
230000009982 effect on human Effects 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
229960001340 histamine Drugs 0.000 description 1
230000001939 inductive effect Effects 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000002075 main ingredient Substances 0.000 description 1
210000002464 muscle smooth vascular Anatomy 0.000 description 1
229960002748 norepinephrine Drugs 0.000 description 1
SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 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
239000000843 powder Substances 0.000 description 1
230000002265 prevention Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229940076279 serotonin Drugs 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
230000008685 targeting Effects 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

JP11718181A 1981-07-28 1981-07-28 新規の１−置換−２−〔（ｎ−モルホリノ−ｎ−ニトロソアミノ）メチル〕−テトラゾ−ル誘導体並びに該誘導体を主成分とする血栓防止剤 Granted JPS5821670A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP11718181A JPS5821670A (ja)	1981-07-28	1981-07-28	新規の１−置換−２−〔（ｎ−モルホリノ−ｎ−ニトロソアミノ）メチル〕−テトラゾ−ル誘導体並びに該誘導体を主成分とする血栓防止剤

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP11718181A JPS5821670A (ja)	1981-07-28	1981-07-28	新規の１−置換−２−〔（ｎ−モルホリノ−ｎ−ニトロソアミノ）メチル〕−テトラゾ−ル誘導体並びに該誘導体を主成分とする血栓防止剤

Publications (2)

Publication Number	Publication Date
JPS5821670A JPS5821670A (ja)	1983-02-08
JPH0222069B2 true JPH0222069B2 (de)	1990-05-17

Family

ID=14705419

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP11718181A Granted JPS5821670A (ja)	1981-07-28	1981-07-28	新規の１−置換−２−〔（ｎ−モルホリノ−ｎ−ニトロソアミノ）メチル〕−テトラゾ−ル誘導体並びに該誘導体を主成分とする血栓防止剤

Country Status (1)

Country	Link
JP (1)	JPS5821670A (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6194435B1 (en)	1996-10-11	2001-02-27	Cor Therapeutics, Inc.	Lactams as selective factor Xa inhibitors

1981
- 1981-07-28 JP JP11718181A patent/JPS5821670A/ja active Granted

Also Published As

Publication number	Publication date
JPS5821670A (ja)	1983-02-08

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EP0388188A1 (de)	1990-09-19	Benzoxepin-Derivate
FR2536398A1 (fr)	1984-05-25	Nouveaux composes heterocycliques
JPH0234951B2 (de)	1990-08-07
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JPH0222069B2 (de)	1990-05-17
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US3737542A (en)	1973-06-05	Lowering excessive serum lipid concentrations and preparations containing fluoro-pyridine derivatives
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US3903083A (en)	1975-09-02	3,3A-Dihydro-2H,9H-isoxazolo(3,2-b)(1,3)benzoxazin-9-ones
US4614743A (en)	1986-09-30	Methods of treating pain and inflammation with 4,7-dimethyl-2-(4-pyridinyl)-1,2,4,-triazolo[1,5-a]pyrimidin-5(4H)-one or the pharmaceutically acceptable salts or solvates thereof
JPH02129183A (ja)	1990-05-17	１−アニリノ−４−（１ｈ−イミダゾール−１−イル）フタラジン誘導体及びそれを有効成分とする血小板凝集抑制剤
JP3553158B2 (ja)	2004-08-11	ピリダジノインドール誘導体
US4024259A (en)	1977-05-17	3-Anilino-2,4-diazabicyclo[3.2.1]octenes