JPS59196816A - 水溶性アズレン誘導体の安定な水溶液の製造法 - Google Patents
水溶性アズレン誘導体の安定な水溶液の製造法Info
- Publication number
- JPS59196816A JPS59196816A JP7193583A JP7193583A JPS59196816A JP S59196816 A JPS59196816 A JP S59196816A JP 7193583 A JP7193583 A JP 7193583A JP 7193583 A JP7193583 A JP 7193583A JP S59196816 A JPS59196816 A JP S59196816A
- Authority
- JP
- Japan
- Prior art keywords
- aqueous solution
- water
- stable aqueous
- cationic surfactant
- nonionic
- 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.)
- Granted
Links
- 239000007864 aqueous solution Substances 0.000 title claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- HPJYKMSFRBJOSW-JHSUYXJUSA-N Damsin Chemical compound C[C@H]1CC[C@H]2C(=C)C(=O)O[C@H]2[C@]2(C)C(=O)CC[C@@H]12 HPJYKMSFRBJOSW-JHSUYXJUSA-N 0.000 title description 2
- 239000003093 cationic surfactant Substances 0.000 claims abstract description 7
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000005520 cutting process Methods 0.000 claims description 2
- 241000102542 Kara Species 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 235000015278 beef Nutrition 0.000 claims 1
- 239000002736 nonionic surfactant Substances 0.000 abstract description 5
- GHXZTYHSJHQHIJ-UHFFFAOYSA-N Chlorhexidine Chemical compound C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 GHXZTYHSJHQHIJ-UHFFFAOYSA-N 0.000 abstract description 4
- 229960003260 chlorhexidine Drugs 0.000 abstract description 4
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 abstract description 4
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 abstract description 4
- 229920000053 polysorbate 80 Polymers 0.000 abstract description 4
- 229940068968 polysorbate 80 Drugs 0.000 abstract description 4
- 239000002244 precipitate Substances 0.000 abstract description 3
- 229960001950 benzethonium chloride Drugs 0.000 abstract description 2
- UREZNYTWGJKWBI-UHFFFAOYSA-M benzethonium chloride Chemical compound [Cl-].C1=CC(C(C)(C)CC(C)(C)C)=CC=C1OCCOCC[N+](C)(C)CC1=CC=CC=C1 UREZNYTWGJKWBI-UHFFFAOYSA-M 0.000 abstract description 2
- 229920002675 Polyoxyl Polymers 0.000 abstract 1
- 229940121363 anti-inflammatory agent Drugs 0.000 abstract 1
- 239000002260 anti-inflammatory agent Substances 0.000 abstract 1
- 230000002421 anti-septic effect Effects 0.000 abstract 1
- 229960000686 benzalkonium chloride Drugs 0.000 abstract 1
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 abstract 1
- 230000002542 deteriorative effect Effects 0.000 abstract 1
- 239000003755 preservative agent Substances 0.000 abstract 1
- 230000002335 preservative effect Effects 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000003889 eye drop Substances 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 229940012356 eye drops Drugs 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical class OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- 239000008213 purified water Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 2
- 229940033663 thimerosal Drugs 0.000 description 2
- CMCBDXRRFKYBDG-UHFFFAOYSA-N 1-dodecoxydodecane Chemical compound CCCCCCCCCCCCOCCCCCCCCCCCC CMCBDXRRFKYBDG-UHFFFAOYSA-N 0.000 description 1
- OIALAIQRYISUEV-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]e Polymers CCCCCCCCCCCCCCCCCC(=O)OCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO OIALAIQRYISUEV-UHFFFAOYSA-N 0.000 description 1
- OHJGXPGLNASSEM-UHFFFAOYSA-N 4-methyl-7-propan-2-ylazulene Chemical compound CC(C)C1=CC=C(C)C2=CC=CC2=C1 OHJGXPGLNASSEM-UHFFFAOYSA-N 0.000 description 1
- YMDPXAHZTLMDHD-UHFFFAOYSA-N 7-ethyl-4-methylazulene Chemical compound CC=1C2=CC=CC2=CC(=CC1)CC YMDPXAHZTLMDHD-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000257465 Echinoidea Species 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- CSQPSQYQIUYADT-UHFFFAOYSA-J S(=S)(=O)([O-])[O-].[Th+4].S(=S)(=O)([O-])[O-] Chemical compound S(=S)(=O)([O-])[O-].[Th+4].S(=S)(=O)([O-])[O-] CSQPSQYQIUYADT-UHFFFAOYSA-J 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- -1 alkyl azulene-3-sulfonate Chemical compound 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 239000005667 attractant Substances 0.000 description 1
- 150000001545 azulenes Chemical class 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 229960003872 benzethonium Drugs 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000031902 chemoattractant activity Effects 0.000 description 1
- XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 description 1
- 229940005991 chloric acid Drugs 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- SIYLLGKDQZGJHK-UHFFFAOYSA-N dimethyl-(phenylmethyl)-[2-[2-[4-(2,4,4-trimethylpentan-2-yl)phenoxy]ethoxy]ethyl]ammonium Chemical compound C1=CC(C(C)(C)CC(C)(C)C)=CC=C1OCCOCC[N+](C)(C)CC1=CC=CC=C1 SIYLLGKDQZGJHK-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 229940050410 gluconate Drugs 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000008141 laxative Substances 0.000 description 1
- 230000002475 laxative effect Effects 0.000 description 1
- 235000020094 liqueur Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940100892 mercury compound Drugs 0.000 description 1
- 150000002731 mercury compounds Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229940067107 phenylethyl alcohol Drugs 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- UPDATVKGFTVGQJ-UHFFFAOYSA-N sodium;azane Chemical compound N.[Na+] UPDATVKGFTVGQJ-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 235000020354 squash Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7193583A JPS59196816A (ja) | 1983-04-22 | 1983-04-22 | 水溶性アズレン誘導体の安定な水溶液の製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7193583A JPS59196816A (ja) | 1983-04-22 | 1983-04-22 | 水溶性アズレン誘導体の安定な水溶液の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59196816A true JPS59196816A (ja) | 1984-11-08 |
| JPH0127060B2 JPH0127060B2 (OSRAM) | 1989-05-26 |
Family
ID=13474862
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7193583A Granted JPS59196816A (ja) | 1983-04-22 | 1983-04-22 | 水溶性アズレン誘導体の安定な水溶液の製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59196816A (OSRAM) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62138438A (ja) * | 1985-12-10 | 1987-06-22 | Zeria Shinyaku Kogyo Kk | 易酸化物質溶液の安定化方法 |
| JPS6348211A (ja) * | 1986-08-19 | 1988-02-29 | Lion Corp | アズレン系抗炎症剤 |
| US5411993A (en) * | 1992-07-13 | 1995-05-02 | Nihon Tenganyaku Kenkyusho Co, Ltd. | Anti-inflammatory, stable aqueous preparation comprising azulene sodium sulfonate and polyhydric alcohol |
| KR100450703B1 (ko) * | 1994-05-17 | 2004-10-01 | 알러간, 인코포레이티드 | 시각 조직에의 국부 도포를 위한 누선 특효 유제 |
| US20090226541A1 (en) * | 2005-03-10 | 2009-09-10 | 3M Innovative Properties Company | Methods of reducing microbial contamination |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51125713A (en) * | 1974-12-27 | 1976-11-02 | Sawai Seiyaku Kk | A process for preparing 1,4-dimethyl-7- isopropylazulene-3-sulfonate q uaternary ammonium salt |
| JPS5420138A (en) * | 1977-07-11 | 1979-02-15 | Sunstar Inc | Oral cavity agent composition |
-
1983
- 1983-04-22 JP JP7193583A patent/JPS59196816A/ja active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51125713A (en) * | 1974-12-27 | 1976-11-02 | Sawai Seiyaku Kk | A process for preparing 1,4-dimethyl-7- isopropylazulene-3-sulfonate q uaternary ammonium salt |
| JPS5420138A (en) * | 1977-07-11 | 1979-02-15 | Sunstar Inc | Oral cavity agent composition |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62138438A (ja) * | 1985-12-10 | 1987-06-22 | Zeria Shinyaku Kogyo Kk | 易酸化物質溶液の安定化方法 |
| JPS6348211A (ja) * | 1986-08-19 | 1988-02-29 | Lion Corp | アズレン系抗炎症剤 |
| US5411993A (en) * | 1992-07-13 | 1995-05-02 | Nihon Tenganyaku Kenkyusho Co, Ltd. | Anti-inflammatory, stable aqueous preparation comprising azulene sodium sulfonate and polyhydric alcohol |
| KR100450703B1 (ko) * | 1994-05-17 | 2004-10-01 | 알러간, 인코포레이티드 | 시각 조직에의 국부 도포를 위한 누선 특효 유제 |
| US20090226541A1 (en) * | 2005-03-10 | 2009-09-10 | 3M Innovative Properties Company | Methods of reducing microbial contamination |
| US10918618B2 (en) * | 2005-03-10 | 2021-02-16 | 3M Innovative Properties Company | Methods of reducing microbial contamination |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0127060B2 (OSRAM) | 1989-05-26 |
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