JPH051791B2 - - Google Patents

Info

Publication number: JPH051791B2
Authority: JP; Japan
Prior art keywords: compound; cyclopropylmethyloxybenzimidazole; atpase; mol; gastric
Prior art date: 1986-03-07
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 - Lifetime

Application number

JP61048260A

Other languages

English (en)

Japanese (ja)

Other versions

JPS62207261A (ja

Inventor

Naoto Matsuishi

Haruki Takeda

Kenichi Iiizumi

Seiichi Murakami

Akira Hisamitsu

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.)

Tokyo Tanabe Co Ltd

Original Assignee

Tokyo Tanabe 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.)

1986-03-07

Filing date

1986-03-07

Publication date

1993-01-11

1986-03-07 Application filed by Tokyo Tanabe Co Ltd filed Critical Tokyo Tanabe Co Ltd

1986-03-07 Priority to JP4826086A priority Critical patent/JPS62207261A/ja

1987-09-11 Publication of JPS62207261A publication Critical patent/JPS62207261A/ja

1993-01-11 Publication of JPH051791B2 publication Critical patent/JPH051791B2/ja

Status Granted legal-status Critical Current

Links

-1 sulfide compound Chemical class 0.000 claims description 22
239000007810 chemical reaction solvent Substances 0.000 claims description 5
239000007800 oxidant agent Substances 0.000 claims description 4
125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
230000001590 oxidative effect Effects 0.000 claims description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
230000000694 effects Effects 0.000 description 15
108091006112 ATPases Proteins 0.000 description 14
102000057290 Adenosine Triphosphatases Human genes 0.000 description 14
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
150000001875 compounds Chemical class 0.000 description 12
229940125904 compound 1 Drugs 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000000243 solution Substances 0.000 description 9
JVIHSTYYPRUSFG-UHFFFAOYSA-N 2-(1h-benzimidazol-2-ylsulfinylmethyl)-n,n-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1CS(=O)C1=NC2=CC=CC=C2N1 JVIHSTYYPRUSFG-UHFFFAOYSA-N 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
230000002401 inhibitory effect Effects 0.000 description 8
150000001556 benzimidazoles Chemical class 0.000 description 7
230000027119 gastric acid secretion Effects 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
230000002496 gastric effect Effects 0.000 description 6
239000000203 mixture Substances 0.000 description 5
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
239000013078 crystal Substances 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
238000000034 method Methods 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
102000004190 Enzymes Human genes 0.000 description 3
108090000790 Enzymes Proteins 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
241000700159 Rattus Species 0.000 description 3
208000007107 Stomach Ulcer Diseases 0.000 description 3
238000000862 absorption spectrum Methods 0.000 description 3
229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 3
239000003814 drug Substances 0.000 description 3
208000000718 duodenal ulcer Diseases 0.000 description 3
238000000921 elemental analysis Methods 0.000 description 3
210000004051 gastric juice Anatomy 0.000 description 3
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
NYFDLZLJFPNXSI-UHFFFAOYSA-N 5-(cyclopropylmethoxy)-1,3-dihydrobenzimidazole-2-thione Chemical compound C1=C2NC(S)=NC2=CC=C1OCC1CC1 NYFDLZLJFPNXSI-UHFFFAOYSA-N 0.000 description 2
SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 description 2
ZKHQWZAMYRWXGA-KQYNXXCUSA-J ATP(4-) Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O)[C@@H](O)[C@H]1O ZKHQWZAMYRWXGA-KQYNXXCUSA-J 0.000 description 2
ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
NDGRHDGMNRMJOP-UHFFFAOYSA-N [2-(chloromethyl)phenyl]-dimethylazanium;chloride Chemical compound Cl.CN(C)C1=CC=CC=C1CCl NDGRHDGMNRMJOP-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
239000003699 antiulcer agent Substances 0.000 description 2
229940125782 compound 2 Drugs 0.000 description 2
239000012530 fluid Substances 0.000 description 2
229910001629 magnesium chloride Inorganic materials 0.000 description 2
229960000381 omeprazole Drugs 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000001103 potassium chloride Substances 0.000 description 2
235000011164 potassium chloride Nutrition 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000010898 silica gel chromatography Methods 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
229940124597 therapeutic agent Drugs 0.000 description 2
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
LOOPTXPHDBONPS-UHFFFAOYSA-N 2-(cyclopropylmethoxy)-1h-benzimidazole Chemical compound N=1C2=CC=CC=C2NC=1OCC1CC1 LOOPTXPHDBONPS-UHFFFAOYSA-N 0.000 description 1
BCURUYDHMCTTNG-UHFFFAOYSA-N 2-[[6-(cyclopropylmethoxy)-1h-benzimidazol-2-yl]sulfinylmethyl]-n,n-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1CS(=O)C(NC1=C2)=NC1=CC=C2OCC1CC1 BCURUYDHMCTTNG-UHFFFAOYSA-N 0.000 description 1
YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
OPALBKPBPLZWFY-UHFFFAOYSA-N 6-(cyclopropylmethoxy)-1H-benzimidazole Chemical compound C1(CC1)COC1=CC2=C(N=CN2)C=C1 OPALBKPBPLZWFY-UHFFFAOYSA-N 0.000 description 1
NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 1
241000700157 Rattus norvegicus Species 0.000 description 1
210000001015 abdomen Anatomy 0.000 description 1
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
239000011609 ammonium molybdate Substances 0.000 description 1
APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 description 1
235000018660 ammonium molybdate Nutrition 0.000 description 1
229940010552 ammonium molybdate Drugs 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000004737 colorimetric analysis Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
229940126214 compound 3 Drugs 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
229940079593 drug Drugs 0.000 description 1
210000001198 duodenum Anatomy 0.000 description 1
210000002472 endoplasmic reticulum Anatomy 0.000 description 1
238000006911 enzymatic reaction Methods 0.000 description 1
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
210000004907 gland Anatomy 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
229910052816 inorganic phosphate Inorganic materials 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000007310 pathophysiology Effects 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
JCBJVAJGLKENNC-UHFFFAOYSA-M potassium ethyl xanthate Chemical compound [K+].CCOC([S-])=S JCBJVAJGLKENNC-UHFFFAOYSA-M 0.000 description 1
229910001414 potassium ion Inorganic materials 0.000 description 1
239000000047 product Substances 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
210000001187 pylorus Anatomy 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

JP4826086A 1986-03-07 1986-03-07 新規なベンズイミダゾール誘導体及びその製法 Granted JPS62207261A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP4826086A JPS62207261A (ja)	1986-03-07	1986-03-07	新規なベンズイミダゾール誘導体及びその製法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP4826086A JPS62207261A (ja)	1986-03-07	1986-03-07	新規なベンズイミダゾール誘導体及びその製法

Publications (2)

Publication Number	Publication Date
JPS62207261A JPS62207261A (ja)	1987-09-11
JPH051791B2 true JPH051791B2 (fr)	1993-01-11

Family

ID=12798468

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP4826086A Granted JPS62207261A (ja)	1986-03-07	1986-03-07	新規なベンズイミダゾール誘導体及びその製法

Country Status (1)

Country	Link
JP (1)	JPS62207261A (fr)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB2161160A (en) *	1984-07-06	1986-01-08	Fisons Plc	Heterocyclic sulphinyl compounds
JPS62145069A (ja) *	1985-12-19	1987-06-29	Taisho Pharmaceut Co Ltd	ベンズイミダゾ−ル誘導体

1986
- 1986-03-07 JP JP4826086A patent/JPS62207261A/ja active Granted

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB2161160A (en) *	1984-07-06	1986-01-08	Fisons Plc	Heterocyclic sulphinyl compounds
JPS62145069A (ja) *	1985-12-19	1987-06-29	Taisho Pharmaceut Co Ltd	ベンズイミダゾ−ル誘導体

Also Published As

Publication number	Publication date
JPS62207261A (ja)	1987-09-11

Publication	Publication Date	Title
KR940002824B1 (ko)	1994-04-04	이미다조[4,5-b]피리딘 유도체 및 그의 제조방법
US4248880A (en)	1981-02-03	Treatment of gastric ulcers with naphthimidazole derivatives
RU2124501C1 (ru)	1999-01-10	Производные салициловой кислоты, их алкиловые эфиры, содержащие от 1 до 6 атомов углерода в эфирной группе, соли и сольваты
JPH045674B2 (fr)	1992-02-03
JPS6025423B2 (ja)	1985-06-18	１，４−ジヒドロピリジンの製法
EP0335646A1 (fr)	1989-10-04	Composés antiviraux
KR880002706B1 (ko)	1988-12-26	설포닐 우레아의 제조방법
JPH051791B2 (fr)	1993-01-11
JPS5877880A (ja)	1983-05-11	テトラゾ−ル誘導体
SU482044A3 (ru)	1975-08-25	Способ получени 4-или 5-нитромидазолов
JPH0680059B2 (ja)	1994-10-12	新規なイソオキサゾール誘導体
JPH0430957B2 (fr)	1992-05-25
JPH01190682A (ja)	1989-07-31	新規なイミダゾ［４，５−ｂ］ピリジン誘導体、その製造法及びそれを含有する抗潰瘍剤
JP2546841B2 (ja)	1996-10-23	新規なイミダゾ〔４，５−ｂ〕ピリジン誘導体、その製造法及びそれを含有する抗潰瘍剤
JPS62145084A (ja)	1987-06-29	イミダゾ〔４，５−ｂ〕ピリジン誘導体
CA1264053A (fr)	1989-12-27	Cyclopropylmethyloxybenzimidazoles
KR900003371B1 (ko)	1990-05-16	설파모일벤조산 유도체의 제조방법
JPH0380158B2 (fr)	1991-12-24
KR810000633B1 (ko)	1981-06-10	이미다졸 유도체의 제조방법
KR950010082B1 (ko)	1995-09-06	프리스티나마이신 ⅱ_b 유도체의 제조 방법
KR960003319B1 (ko)	1996-03-08	신규한 엔(n)-아릴설포닐-2-이미다졸리디논 유도체 및 그의 제조방법
JPS5843958A (ja)	1983-03-14	５（６）−フエニルスルホニルオキシ−ベンズイミダゾ−ル誘導体
JPS62175481A (ja)	1987-08-01	新規なスルホキシド体およびその製造法
JPH0674257B2 (ja)	1994-09-21	新規なスルホキシド体およびその製造法
JPH01121271A (ja)	1989-05-12	２−置換シクロヘプトイミダゾール誘導体、抗潰瘍剤並びにその製造方法