JPS6152146B2 - - Google Patents
Info
- Publication number
- JPS6152146B2 JPS6152146B2 JP3964081A JP3964081A JPS6152146B2 JP S6152146 B2 JPS6152146 B2 JP S6152146B2 JP 3964081 A JP3964081 A JP 3964081A JP 3964081 A JP3964081 A JP 3964081A JP S6152146 B2 JPS6152146 B2 JP S6152146B2
- Authority
- JP
- Japan
- Prior art keywords
- pge
- cyclodextrin
- compounds
- pgf
- prostaglandin
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims description 25
- 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 claims description 24
- 229920000858 Cyclodextrin Polymers 0.000 claims description 16
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 12
- 229920001542 oligosaccharide Polymers 0.000 claims description 9
- 150000002482 oligosaccharides Chemical class 0.000 claims description 9
- 238000004108 freeze drying Methods 0.000 claims description 4
- 230000006641 stabilisation Effects 0.000 claims description 4
- 238000011105 stabilization Methods 0.000 claims description 4
- DZUXGQBLFALXCR-UHFFFAOYSA-N (+)-(9alpha,11alpha,13E,15S)-9,11,15-trihydroxyprost-13-en-1-oic acid Natural products CCCCCC(O)C=CC1C(O)CC(O)C1CCCCCCC(O)=O DZUXGQBLFALXCR-UHFFFAOYSA-N 0.000 claims 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 21
- 150000003180 prostaglandins Chemical group 0.000 description 12
- 238000000034 method Methods 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 8
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 8
- 230000000694 effects Effects 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 description 5
- 230000000087 stabilizing effect Effects 0.000 description 5
- 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 4
- 239000008101 lactose Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 208000007536 Thrombosis Diseases 0.000 description 3
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 150000004676 glycans Chemical class 0.000 description 3
- 229920001282 polysaccharide Polymers 0.000 description 3
- 239000005017 polysaccharide Substances 0.000 description 3
- 229920001450 Alpha-Cyclodextrin Polymers 0.000 description 2
- 206010003210 Arteriosclerosis Diseases 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 229940043377 alpha-cyclodextrin Drugs 0.000 description 2
- 208000011775 arteriosclerosis disease Diseases 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- 229960004853 betadex Drugs 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- -1 prostaglandins Chemical class 0.000 description 2
- 210000002460 smooth muscle Anatomy 0.000 description 2
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 2
- 238000011146 sterile filtration Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 1
- 229930182837 (R)-adrenaline Natural products 0.000 description 1
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
- DPOINJQWXDTOSF-DODZYUBVSA-N 13,14-Dihydro PGE1 Chemical compound CCCCC[C@H](O)CC[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O DPOINJQWXDTOSF-DODZYUBVSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 239000001116 FEMA 4028 Substances 0.000 description 1
- 208000031226 Hyperlipidaemia Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- MUPFEKGTMRGPLJ-RMMQSMQOSA-N Raffinose Natural products O(C[C@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O[C@@]2(CO)[C@H](O)[C@@H](O)[C@@H](CO)O2)O1)[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 MUPFEKGTMRGPLJ-RMMQSMQOSA-N 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- MUPFEKGTMRGPLJ-UHFFFAOYSA-N UNPD196149 Natural products OC1C(O)C(CO)OC1(CO)OC1C(O)C(O)C(O)C(COC2C(C(O)C(O)C(CO)O2)O)O1 MUPFEKGTMRGPLJ-UHFFFAOYSA-N 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 229930003268 Vitamin C Natural products 0.000 description 1
- 239000004015 abortifacient agent Substances 0.000 description 1
- 231100000641 abortifacient agent Toxicity 0.000 description 1
- 206010000210 abortion Diseases 0.000 description 1
- 231100000176 abortion Toxicity 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 230000003243 anti-lipolytic effect Effects 0.000 description 1
- 235000011175 beta-cyclodextrine Nutrition 0.000 description 1
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000003182 bronchodilatating effect Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000003727 cerebral blood flow Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 150000002016 disaccharides Chemical class 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229960005139 epinephrine Drugs 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- GDSRMADSINPKSL-HSEONFRVSA-N gamma-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 description 1
- 229940080345 gamma-cyclodextrin Drugs 0.000 description 1
- 210000004051 gastric juice Anatomy 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 208000003243 intestinal obstruction Diseases 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 239000008141 laxative Substances 0.000 description 1
- 230000002475 laxative effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 229940127234 oral contraceptive Drugs 0.000 description 1
- 239000003539 oral contraceptive agent Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000008855 peristalsis Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 210000002826 placenta Anatomy 0.000 description 1
- 230000002980 postoperative effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- GMVPRGQOIOIIMI-DWKJAMRDSA-N prostaglandin E1 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O GMVPRGQOIOIIMI-DWKJAMRDSA-N 0.000 description 1
- DZUXGQBLFALXCR-CDIPTNKSSA-N prostaglandin F1alpha Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1CCCCCCC(O)=O DZUXGQBLFALXCR-CDIPTNKSSA-N 0.000 description 1
- WGJJROVFWIXTPA-OALUTQOASA-N prostanoic acid Chemical class CCCCCCCC[C@H]1CCC[C@@H]1CCCCCCC(O)=O WGJJROVFWIXTPA-OALUTQOASA-N 0.000 description 1
- MUPFEKGTMRGPLJ-ZQSKZDJDSA-N raffinose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)O1 MUPFEKGTMRGPLJ-ZQSKZDJDSA-N 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 150000004043 trisaccharides Chemical class 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3964081A JPS57156460A (en) | 1981-03-20 | 1981-03-20 | Stabilized composition of prostaglandin and prostaglandin mimic compound, and its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3964081A JPS57156460A (en) | 1981-03-20 | 1981-03-20 | Stabilized composition of prostaglandin and prostaglandin mimic compound, and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57156460A JPS57156460A (en) | 1982-09-27 |
| JPS6152146B2 true JPS6152146B2 (en, 2012) | 1986-11-12 |
Family
ID=12558683
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3964081A Granted JPS57156460A (en) | 1981-03-20 | 1981-03-20 | Stabilized composition of prostaglandin and prostaglandin mimic compound, and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57156460A (en, 2012) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008099907A1 (ja) | 2007-02-16 | 2008-08-21 | Ono Pharmaceutical Co., Ltd. | 尿排出障害治療剤 |
| WO2008136519A1 (ja) | 2007-05-08 | 2008-11-13 | National University Corporation, Hamamatsu University School Of Medicine | Ｅｐ４アゴニストを含有してなる細胞傷害性ｔ細胞の活性化剤 |
| EP2255829A2 (en) | 2001-07-23 | 2010-12-01 | Ono Pharmaceutical Co., Ltd. | Pharmaceutical composition for treatment of diseases associated with decrease in bone mass comprising EP4 agonist as active ingredient |
| WO2010143661A1 (ja) | 2009-06-10 | 2010-12-16 | 小野薬品工業株式会社 | 膀胱排尿筋収縮および尿道括約筋弛緩作用を有する化合物 |
| JP4890657B1 (ja) * | 2011-06-03 | 2012-03-07 | 小野薬品工業株式会社 | リマプロストとβ−シクロデキストリンを含有する錠剤 |
| EP2465537A1 (en) | 2002-10-10 | 2012-06-20 | ONO Pharmaceutical Co., Ltd. | Microspheres comprising ONO-1301 |
| WO2013018837A1 (ja) | 2011-08-02 | 2013-02-07 | 小野薬品工業株式会社 | 左室拡張機能改善剤 |
| WO2014034902A1 (ja) | 2012-08-31 | 2014-03-06 | 小野薬品工業株式会社 | アミン塩とその結晶 |
| WO2017195762A1 (ja) | 2016-05-09 | 2017-11-16 | 旭硝子株式会社 | 新規なプロスタグランジン誘導体 |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5818357A (ja) * | 1981-07-28 | 1983-02-02 | Ono Pharmaceut Co Ltd | ６，９−メタノ−ｐｇｉ↓２及び６，９−メタノ−ｐｇｉ↓２類似化合物の安定化組成物及びその製造方法 |
| DE3304864A1 (de) * | 1983-02-12 | 1984-08-16 | Bayer Ag, 5090 Leverkusen | Adsorbate von prostaglandinen |
| DE4309579C3 (de) * | 1993-03-24 | 2000-01-27 | Sanol Arznei Schwarz Gmbh | Pharmazeutische Zusammensetzung in Form einer Packung |
| TWI319322B (en) * | 2003-11-13 | 2010-01-11 | Ono Pharmaceutical Co | Frozen-dried preperation containing prostaglandin |
| 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 |
| JPWO2006075690A1 (ja) * | 2005-01-14 | 2008-06-12 | 小野薬品工業株式会社 | 安定な医薬組成物 |
| US20100016427A1 (en) * | 2006-08-11 | 2010-01-21 | Taishio Pharmaceutical Co., Ltd. | External preparation comprising prostaglandin derivative |
-
1981
- 1981-03-20 JP JP3964081A patent/JPS57156460A/ja active Granted
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2255829A2 (en) | 2001-07-23 | 2010-12-01 | Ono Pharmaceutical Co., Ltd. | Pharmaceutical composition for treatment of diseases associated with decrease in bone mass comprising EP4 agonist as active ingredient |
| EP2465537A1 (en) | 2002-10-10 | 2012-06-20 | ONO Pharmaceutical Co., Ltd. | Microspheres comprising ONO-1301 |
| WO2008099907A1 (ja) | 2007-02-16 | 2008-08-21 | Ono Pharmaceutical Co., Ltd. | 尿排出障害治療剤 |
| WO2008136519A1 (ja) | 2007-05-08 | 2008-11-13 | National University Corporation, Hamamatsu University School Of Medicine | Ｅｐ４アゴニストを含有してなる細胞傷害性ｔ細胞の活性化剤 |
| WO2010143661A1 (ja) | 2009-06-10 | 2010-12-16 | 小野薬品工業株式会社 | 膀胱排尿筋収縮および尿道括約筋弛緩作用を有する化合物 |
| JP4890657B1 (ja) * | 2011-06-03 | 2012-03-07 | 小野薬品工業株式会社 | リマプロストとβ−シクロデキストリンを含有する錠剤 |
| CN103619339A (zh) * | 2011-06-03 | 2014-03-05 | 小野药品工业株式会社 | 含有利马前列素和β-环糊精的片剂 |
| WO2013018837A1 (ja) | 2011-08-02 | 2013-02-07 | 小野薬品工業株式会社 | 左室拡張機能改善剤 |
| WO2014034902A1 (ja) | 2012-08-31 | 2014-03-06 | 小野薬品工業株式会社 | アミン塩とその結晶 |
| WO2017195762A1 (ja) | 2016-05-09 | 2017-11-16 | 旭硝子株式会社 | 新規なプロスタグランジン誘導体 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57156460A (en) | 1982-09-27 |
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