JPH0725771B2 - ２−アミノエタンスルホン酸亜鉛錯化合物 - Google Patents
２−アミノエタンスルホン酸亜鉛錯化合物Info
- Publication number
- JPH0725771B2 JPH0725771B2 JP4186090A JP18609092A JPH0725771B2 JP H0725771 B2 JPH0725771 B2 JP H0725771B2 JP 4186090 A JP4186090 A JP 4186090A JP 18609092 A JP18609092 A JP 18609092A JP H0725771 B2 JPH0725771 B2 JP H0725771B2
- Authority
- JP
- Japan
- Prior art keywords
- aminoethanesulfonic acid
- compound
- zinc
- complex compound
- zinc complex
- 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 - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 title claims description 30
- CKRMSFRODRPAEF-UHFFFAOYSA-N 2-aminoethanesulfonic acid;zinc Chemical compound [Zn].NCCS(O)(=O)=O CKRMSFRODRPAEF-UHFFFAOYSA-N 0.000 title claims description 8
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 claims description 30
- 229960003080 taurine Drugs 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- 208000006454 hepatitis Diseases 0.000 claims description 10
- 150000003752 zinc compounds Chemical class 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- -1 alkali metal salt Chemical class 0.000 claims description 7
- 239000003699 antiulcer agent Substances 0.000 claims description 4
- 210000004185 liver Anatomy 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000012360 testing method Methods 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 241000700159 Rattus Species 0.000 description 11
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 230000003908 liver function Effects 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- 239000011701 zinc Substances 0.000 description 8
- 230000000767 anti-ulcer Effects 0.000 description 7
- 230000037396 body weight Effects 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 6
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 6
- 230000002401 inhibitory effect Effects 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
- 210000002784 stomach Anatomy 0.000 description 5
- 229910052725 zinc Inorganic materials 0.000 description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- 208000025865 Ulcer Diseases 0.000 description 4
- 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 4
- 239000001768 carboxy methyl cellulose Substances 0.000 description 4
- 210000003494 hepatocyte Anatomy 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 4
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 4
- 231100000397 ulcer Toxicity 0.000 description 4
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 4
- 102100036475 Alanine aminotransferase 1 Human genes 0.000 description 3
- 108010082126 Alanine transaminase Proteins 0.000 description 3
- 108010003415 Aspartate Aminotransferases Proteins 0.000 description 3
- 102000004625 Aspartate Aminotransferases Human genes 0.000 description 3
- 108010024636 Glutathione Proteins 0.000 description 3
- 239000004378 Glycyrrhizin Substances 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229960003180 glutathione Drugs 0.000 description 3
- LPLVUJXQOOQHMX-UHFFFAOYSA-N glycyrrhetinic acid glycoside Natural products C1CC(C2C(C3(CCC4(C)CCC(C)(CC4C3=CC2=O)C(O)=O)C)(C)CC2)(C)C2C(C)(C)C1OC1OC(C(O)=O)C(O)C(O)C1OC1OC(C(O)=O)C(O)C(O)C1O LPLVUJXQOOQHMX-UHFFFAOYSA-N 0.000 description 3
- 229960004949 glycyrrhizic acid Drugs 0.000 description 3
- UYRUBYNTXSDKQT-UHFFFAOYSA-N glycyrrhizic acid Natural products CC1(C)C(CCC2(C)C1CCC3(C)C2C(=O)C=C4C5CC(C)(CCC5(C)CCC34C)C(=O)O)OC6OC(C(O)C(O)C6OC7OC(O)C(O)C(O)C7C(=O)O)C(=O)O UYRUBYNTXSDKQT-UHFFFAOYSA-N 0.000 description 3
- 235000019410 glycyrrhizin Nutrition 0.000 description 3
- LPLVUJXQOOQHMX-QWBHMCJMSA-N glycyrrhizinic acid Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@@H]1O[C@@H]1C([C@H]2[C@]([C@@H]3[C@@]([C@@]4(CC[C@@]5(C)CC[C@@](C)(C[C@H]5C4=CC3=O)C(O)=O)C)(C)CC2)(C)CC1)(C)C)C(O)=O)[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O LPLVUJXQOOQHMX-QWBHMCJMSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- KLQISSYTHCEUKQ-UHFFFAOYSA-N 2-aminoethanesulfonic acid zinc Chemical compound [Zn].NCCS(O)(=O)=O.NCCS(O)(=O)=O KLQISSYTHCEUKQ-UHFFFAOYSA-N 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- 239000012981 Hank's balanced salt solution Substances 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 241000700157 Rattus norvegicus Species 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 230000000762 glandular Effects 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 231100000518 lethal Toxicity 0.000 description 2
- 230000001665 lethal effect Effects 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- 229940102001 zinc bromide Drugs 0.000 description 2
- UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 description 2
- KERCCVBWXLGNGI-UHFFFAOYSA-N 1-aminoethanesulfonic acid zinc Chemical compound [Zn].NC(C)S(=O)(=O)O KERCCVBWXLGNGI-UHFFFAOYSA-N 0.000 description 1
- HOHIAEPXOHCCGW-UHFFFAOYSA-N 2-aminoethanesulfonic acid Chemical compound NCCS(O)(=O)=O.NCCS(O)(=O)=O HOHIAEPXOHCCGW-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 102000029816 Collagenase Human genes 0.000 description 1
- 108060005980 Collagenase Proteins 0.000 description 1
- 206010067125 Liver injury Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- GHVZOJONCUEWAV-UHFFFAOYSA-N [K].CCO Chemical compound [K].CCO GHVZOJONCUEWAV-UHFFFAOYSA-N 0.000 description 1
- 230000003187 abdominal effect Effects 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 1
- 238000011047 acute toxicity test Methods 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- JTDNJBUOVNNSOG-UHFFFAOYSA-N amino ethanesulfonate Chemical compound CCS(=O)(=O)ON JTDNJBUOVNNSOG-UHFFFAOYSA-N 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 210000002376 aorta thoracic Anatomy 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 229960002424 collagenase Drugs 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001784 detoxification Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 231100000753 hepatic injury Toxicity 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000011533 pre-incubation Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- SUBJHSREKVAVAR-UHFFFAOYSA-N sodium;methanol;methanolate Chemical compound [Na+].OC.[O-]C SUBJHSREKVAVAR-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 210000002417 xiphoid bone Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/13—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
- C07C309/14—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton containing amino groups bound to the carbon skeleton
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/28—Compounds containing heavy metals
- A61K31/315—Zinc compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Gastroenterology & Hepatology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4186090A JPH0725771B2 (ja) | 1992-06-18 | 1992-06-18 | ２−アミノエタンスルホン酸亜鉛錯化合物 |
| PCT/JP1993/000813 WO1993025558A1 (fr) | 1992-06-18 | 1993-06-14 | Compose complexe acide 2-aminoethanesulfonique/zinc |
| DE69314794T DE69314794T2 (de) | 1992-06-18 | 1993-06-14 | Komplex von 2-aminäthansulfonsäure und zink |
| US08/356,305 US5489609A (en) | 1992-06-18 | 1993-06-14 | 2-aminoethanesulfonic acid zinc complex compound |
| EP93913534A EP0646586B1 (en) | 1992-06-18 | 1993-06-14 | 2-aminoethanesulfonic acid/zinc complex compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4186090A JPH0725771B2 (ja) | 1992-06-18 | 1992-06-18 | ２−アミノエタンスルホン酸亜鉛錯化合物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0649077A JPH0649077A (ja) | 1994-02-22 |
| JPH0725771B2 true JPH0725771B2 (ja) | 1995-03-22 |
Family
ID=16182196
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4186090A Expired - Lifetime JPH0725771B2 (ja) | 1992-06-18 | 1992-06-18 | ２−アミノエタンスルホン酸亜鉛錯化合物 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US5489609A (enExample) |
| EP (1) | EP0646586B1 (enExample) |
| JP (1) | JPH0725771B2 (enExample) |
| DE (1) | DE69314794T2 (enExample) |
| WO (1) | WO1993025558A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0670070B2 (ja) * | 1992-01-14 | 1994-09-07 | 財団法人生産開発科学研究所 | ２−アミノエタンスルホン酸亜鉛錯体 |
| JP3837769B2 (ja) * | 1995-06-12 | 2006-10-25 | 大塚製薬株式会社 | 抗ウイルス剤 |
| WO2019107196A1 (ja) | 2017-11-30 | 2019-06-06 | ダウ・東レ株式会社 | 硬化性シリコーンゴム組成物 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5292605A (en) * | 1976-01-26 | 1977-08-04 | Canon Kk | Thermoodeveloping photoosensitive material for electrostatic printing master |
| FR2457281A1 (fr) * | 1979-05-23 | 1980-12-19 | Meram Lab | Nouveaux derives de l'acide 3-aminopropanesulfonique ayant une activite membranaire renforcee |
| GB8515170D0 (en) * | 1985-06-14 | 1985-07-17 | Geistlich Soehne Ag | Pharmaceutical compositions |
| JPH0670070B2 (ja) * | 1992-01-14 | 1994-09-07 | 財団法人生産開発科学研究所 | ２−アミノエタンスルホン酸亜鉛錯体 |
-
1992
- 1992-06-18 JP JP4186090A patent/JPH0725771B2/ja not_active Expired - Lifetime
-
1993
- 1993-06-14 DE DE69314794T patent/DE69314794T2/de not_active Expired - Fee Related
- 1993-06-14 US US08/356,305 patent/US5489609A/en not_active Expired - Fee Related
- 1993-06-14 WO PCT/JP1993/000813 patent/WO1993025558A1/ja not_active Ceased
- 1993-06-14 EP EP93913534A patent/EP0646586B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP0646586A4 (enExample) | 1995-05-10 |
| EP0646586A1 (en) | 1995-04-05 |
| DE69314794D1 (de) | 1997-11-27 |
| WO1993025558A1 (fr) | 1993-12-23 |
| DE69314794T2 (de) | 1998-02-26 |
| US5489609A (en) | 1996-02-06 |
| EP0646586B1 (en) | 1997-10-22 |
| JPH0649077A (ja) | 1994-02-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 19950905 |