JPS61171421A - 安定なプロスタグランジンｅ類製剤の製造方法 - Google Patents
安定なプロスタグランジンｅ類製剤の製造方法Info
- Publication number
- JPS61171421A JPS61171421A JP18523085A JP18523085A JPS61171421A JP S61171421 A JPS61171421 A JP S61171421A JP 18523085 A JP18523085 A JP 18523085A JP 18523085 A JP18523085 A JP 18523085A JP S61171421 A JPS61171421 A JP S61171421A
- Authority
- JP
- Japan
- Prior art keywords
- prostaglandin
- water
- solution
- amount
- ethanol
- 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
- XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 title claims abstract description 28
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- -1 thiol compound Chemical class 0.000 claims abstract description 12
- KXGVEGMKQFWNSR-LLQZFEROSA-N deoxycholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 KXGVEGMKQFWNSR-LLQZFEROSA-N 0.000 claims abstract description 10
- 229960003964 deoxycholic acid Drugs 0.000 claims abstract description 10
- KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 229920000642 polymer Polymers 0.000 claims abstract description 8
- 229920002307 Dextran Polymers 0.000 claims abstract description 7
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims abstract description 6
- 239000000126 substance Substances 0.000 claims abstract description 5
- 239000004475 Arginine Substances 0.000 claims abstract description 4
- 239000004375 Dextrin Substances 0.000 claims abstract description 4
- 229920001353 Dextrin Polymers 0.000 claims abstract description 4
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims abstract description 4
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims abstract description 4
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000004472 Lysine Substances 0.000 claims abstract description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 4
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 4
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims abstract description 4
- 235000019425 dextrin Nutrition 0.000 claims abstract description 4
- 230000007721 medicinal effect Effects 0.000 claims abstract description 4
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 5
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 5
- 108010010803 Gelatin Proteins 0.000 claims description 3
- 239000001913 cellulose Substances 0.000 claims description 3
- 229920002678 cellulose Polymers 0.000 claims description 3
- 238000004108 freeze drying Methods 0.000 claims description 3
- 239000008273 gelatin Substances 0.000 claims description 3
- 229920000159 gelatin Polymers 0.000 claims description 3
- 235000019322 gelatine Nutrition 0.000 claims description 3
- 235000011852 gelatine desserts Nutrition 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 abstract description 10
- 150000001875 compounds Chemical class 0.000 abstract description 8
- 239000000203 mixture Substances 0.000 abstract description 7
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 abstract description 2
- 235000018417 cysteine Nutrition 0.000 abstract description 2
- 208000025865 Ulcer Diseases 0.000 abstract 1
- 230000008602 contraction Effects 0.000 abstract 1
- 230000001077 hypotensive effect Effects 0.000 abstract 1
- 210000004798 organs belonging to the digestive system Anatomy 0.000 abstract 1
- 230000003405 preventing effect Effects 0.000 abstract 1
- 231100000397 ulcer Toxicity 0.000 abstract 1
- 230000000304 vasodilatating effect Effects 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 76
- 239000000243 solution Substances 0.000 description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 239000012153 distilled water Substances 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 239000013078 crystal Substances 0.000 description 11
- 229910001873 dinitrogen Inorganic materials 0.000 description 10
- 238000007796 conventional method Methods 0.000 description 8
- 238000011146 sterile filtration Methods 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 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
- 238000003756 stirring Methods 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 4
- 108010024636 Glutathione Proteins 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229960003180 glutathione Drugs 0.000 description 3
- 238000010561 standard procedure Methods 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 108010053070 Glutathione Disulfide Proteins 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229960002986 dinoprostone Drugs 0.000 description 2
- YPZRWBKMTBYPTK-BJDJZHNGSA-N glutathione disulfide Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@H](C(=O)NCC(O)=O)CSSC[C@@H](C(=O)NCC(O)=O)NC(=O)CC[C@H](N)C(O)=O YPZRWBKMTBYPTK-BJDJZHNGSA-N 0.000 description 2
- YPZRWBKMTBYPTK-UHFFFAOYSA-N oxidized gamma-L-glutamyl-L-cysteinylglycine Natural products OC(=O)C(N)CCC(=O)NC(C(=O)NCC(O)=O)CSSCC(C(=O)NCC(O)=O)NC(=O)CCC(N)C(O)=O YPZRWBKMTBYPTK-UHFFFAOYSA-N 0.000 description 2
- 150000003180 prostaglandins Chemical class 0.000 description 2
- FZWBNHMXJMCXLU-UHFFFAOYSA-N 2,3,4,5-tetrahydroxy-6-[3,4,5-trihydroxy-6-[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyhexanal Chemical compound OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OCC(O)C(O)C(O)C(O)C=O)O1 FZWBNHMXJMCXLU-UHFFFAOYSA-N 0.000 description 1
- 206010061459 Gastrointestinal ulcer Diseases 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 1
- PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- NJUISRMVIKYYCN-UHFFFAOYSA-N acetic acid;chloroform;methanol;hydrate Chemical compound O.OC.CC(O)=O.ClC(Cl)Cl NJUISRMVIKYYCN-UHFFFAOYSA-N 0.000 description 1
- 229960004308 acetylcysteine Drugs 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 230000003182 bronchodilatating effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 229960002433 cysteine Drugs 0.000 description 1
- 229940119743 dextran 70 Drugs 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- CBOMORHDRONZRN-QLOYDKTKSA-N prostaglandin E3 Chemical compound CC\C=C/C[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O CBOMORHDRONZRN-QLOYDKTKSA-N 0.000 description 1
- 230000028503 regulation of lipid metabolic process Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 239000003860 topical agent Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18523085A JPS61171421A (ja) | 1985-08-23 | 1985-08-23 | 安定なプロスタグランジンｅ類製剤の製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18523085A JPS61171421A (ja) | 1985-08-23 | 1985-08-23 | 安定なプロスタグランジンｅ類製剤の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61171421A true JPS61171421A (ja) | 1986-08-02 |
| JPS6216929B2 JPS6216929B2 (enrdf_load_stackoverflow) | 1987-04-15 |
Family
ID=16167151
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP18523085A Granted JPS61171421A (ja) | 1985-08-23 | 1985-08-23 | 安定なプロスタグランジンｅ類製剤の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61171421A (enrdf_load_stackoverflow) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005272458A (ja) * | 2004-02-27 | 2005-10-06 | Ono Pharmaceut Co Ltd | 経口投与用医薬組成物 |
| JP2005314413A (ja) * | 2004-04-02 | 2005-11-10 | Ono Pharmaceut Co Ltd | 経口投与用医薬組成物 |
| WO2006057637A1 (en) * | 2004-11-24 | 2006-06-01 | Seo Hong Yoo | Dried forms of aqueous solubilized bile acid dosage formulation: preparation and uses thereof |
| US7772220B2 (en) | 2004-10-15 | 2010-08-10 | Seo Hong Yoo | Methods and compositions for reducing toxicity of a pharmaceutical compound |
| US7932243B2 (en) | 1998-07-24 | 2011-04-26 | Seo Hong Yoo | Bile preparations for gastrointestinal disorders |
| US8173627B2 (en) | 2004-08-30 | 2012-05-08 | Seo Hong Yoo | Neuroprotective effect of solubilized UDCA in focal ischemic model |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5976017A (ja) * | 1983-01-20 | 1984-04-28 | Yamanouchi Pharmaceut Co Ltd | 安定なプロスタグランジンｅ類製剤の製法 |
-
1985
- 1985-08-23 JP JP18523085A patent/JPS61171421A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5976017A (ja) * | 1983-01-20 | 1984-04-28 | Yamanouchi Pharmaceut Co Ltd | 安定なプロスタグランジンｅ類製剤の製法 |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7932243B2 (en) | 1998-07-24 | 2011-04-26 | Seo Hong Yoo | Bile preparations for gastrointestinal disorders |
| JP2005272458A (ja) * | 2004-02-27 | 2005-10-06 | Ono Pharmaceut Co Ltd | 経口投与用医薬組成物 |
| JP2005314413A (ja) * | 2004-04-02 | 2005-11-10 | Ono Pharmaceut Co Ltd | 経口投与用医薬組成物 |
| US8173627B2 (en) | 2004-08-30 | 2012-05-08 | Seo Hong Yoo | Neuroprotective effect of solubilized UDCA in focal ischemic model |
| US7772220B2 (en) | 2004-10-15 | 2010-08-10 | Seo Hong Yoo | Methods and compositions for reducing toxicity of a pharmaceutical compound |
| WO2006057637A1 (en) * | 2004-11-24 | 2006-06-01 | Seo Hong Yoo | Dried forms of aqueous solubilized bile acid dosage formulation: preparation and uses thereof |
| JP2008521800A (ja) * | 2004-11-24 | 2008-06-26 | セオ ホン ユー | 水可溶化胆汁酸投薬処方の乾燥形態、その製造方法及び用途 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6216929B2 (enrdf_load_stackoverflow) | 1987-04-15 |
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