JP5197955B2 - 結晶性デキスロキシグルミドの製造法 - Google Patents
結晶性デキスロキシグルミドの製造法 Download PDFInfo
- Publication number
- JP5197955B2 JP5197955B2 JP2006516595A JP2006516595A JP5197955B2 JP 5197955 B2 JP5197955 B2 JP 5197955B2 JP 2006516595 A JP2006516595 A JP 2006516595A JP 2006516595 A JP2006516595 A JP 2006516595A JP 5197955 B2 JP5197955 B2 JP 5197955B2
- Authority
- JP
- Japan
- Prior art keywords
- crystalline
- dexoxyglumide
- particle size
- less
- value
- 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 - Fee Related
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 20
- 238000002425 crystallisation Methods 0.000 claims abstract description 17
- 230000008025 crystallization Effects 0.000 claims abstract description 15
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims abstract description 13
- QNQZBKQEIFTHFZ-GOSISDBHSA-N dexloxiglumide Chemical compound CCCCCN(CCCOC)C(=O)[C@@H](CCC(O)=O)NC(=O)C1=CC=C(Cl)C(Cl)=C1 QNQZBKQEIFTHFZ-GOSISDBHSA-N 0.000 claims abstract description 3
- 229950010525 dexloxiglumide Drugs 0.000 claims abstract description 3
- 239000002245 particle Substances 0.000 claims description 31
- 238000009826 distribution Methods 0.000 claims description 22
- 239000013078 crystal Substances 0.000 claims description 19
- 239000000843 powder Substances 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 13
- 239000012043 crude product Substances 0.000 claims description 5
- 238000000691 measurement method Methods 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000010419 fine particle Substances 0.000 claims description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 229920002472 Starch Polymers 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000000314 lubricant Substances 0.000 claims description 2
- 235000019359 magnesium stearate Nutrition 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- 235000012239 silicon dioxide Nutrition 0.000 claims description 2
- 229940023144 sodium glycolate Drugs 0.000 claims description 2
- 235000019698 starch Nutrition 0.000 claims description 2
- 239000008107 starch Substances 0.000 claims description 2
- 239000000454 talc Substances 0.000 claims description 2
- 229910052623 talc Inorganic materials 0.000 claims description 2
- 235000012222 talc Nutrition 0.000 claims description 2
- JEJAMASKDTUEBZ-UHFFFAOYSA-N tris(1,1,3-tribromo-2,2-dimethylpropyl) phosphate Chemical compound BrCC(C)(C)C(Br)(Br)OP(=O)(OC(Br)(Br)C(C)(C)CBr)OC(Br)(Br)C(C)(C)CBr JEJAMASKDTUEBZ-UHFFFAOYSA-N 0.000 claims description 2
- -1 disaggregants Substances 0.000 claims 2
- 229920000168 Microcrystalline cellulose Polymers 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 239000004615 ingredient Substances 0.000 claims 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 claims 1
- 239000008108 microcrystalline cellulose Substances 0.000 claims 1
- 229940016286 microcrystalline cellulose Drugs 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 6
- 238000000746 purification Methods 0.000 abstract description 4
- 230000000877 morphologic effect Effects 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 238000005259 measurement Methods 0.000 description 6
- 230000001476 alcoholic effect Effects 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 4
- 238000007906 compression Methods 0.000 description 4
- 230000006835 compression Effects 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000007916 tablet composition Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 208000004998 Abdominal Pain Diseases 0.000 description 1
- 102100025841 Cholecystokinin Human genes 0.000 description 1
- 101800001982 Cholecystokinin Proteins 0.000 description 1
- LCSMDUWISSYJBW-LJQANCHMSA-N ClC=1C=C(C(=O)N[C@H](CCC)C(=O)N(CCCCC)CCCOC)C=CC1Cl Chemical compound ClC=1C=C(C(=O)N[C@H](CCC)C(=O)N(CCCCC)CCCOC)C=CC1Cl LCSMDUWISSYJBW-LJQANCHMSA-N 0.000 description 1
- 208000002881 Colic Diseases 0.000 description 1
- 208000017228 Gastrointestinal motility disease Diseases 0.000 description 1
- 101000807541 Homo sapiens Ubiquitin carboxyl-terminal hydrolase 24 Proteins 0.000 description 1
- 206010033645 Pancreatitis Diseases 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- 102100037176 Ubiquitin carboxyl-terminal hydrolase 24 Human genes 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 208000003770 biliary dyskinesia Diseases 0.000 description 1
- 230000002902 bimodal effect Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229940107137 cholecystokinin Drugs 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000007922 dissolution test Methods 0.000 description 1
- 201000006549 dyspepsia Diseases 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 208000001130 gallstones Diseases 0.000 description 1
- 208000021302 gastroesophageal reflux disease Diseases 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 208000002551 irritable bowel syndrome Diseases 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000007431 microscopic evaluation Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- IZTQOLKUZKXIRV-YRVFCXMDSA-N sincalide Chemical compound C([C@@H](C(=O)N[C@@H](CCSC)C(=O)NCC(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](N)CC(O)=O)C1=CC=C(OS(O)(=O)=O)C=C1 IZTQOLKUZKXIRV-YRVFCXMDSA-N 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/22—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
-
- 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
-
- 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
- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Gastroenterology & Hepatology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT000474A ITTO20030474A1 (it) | 2003-06-23 | 2003-06-23 | Procedimento per la preparazione di dexloxiglumide |
| ITTO2003A000474 | 2003-06-23 | ||
| PCT/IB2004/002208 WO2004113271A2 (en) | 2003-06-23 | 2004-06-21 | A method for the preparation of crystalline dexloxiglumide |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007521253A JP2007521253A (ja) | 2007-08-02 |
| JP2007521253A5 JP2007521253A5 (https=) | 2012-10-11 |
| JP5197955B2 true JP5197955B2 (ja) | 2013-05-15 |
Family
ID=33524063
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006516595A Expired - Fee Related JP5197955B2 (ja) | 2003-06-23 | 2004-06-21 | 結晶性デキスロキシグルミドの製造法 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US7662994B2 (https=) |
| EP (1) | EP1646607B1 (https=) |
| JP (1) | JP5197955B2 (https=) |
| AT (1) | ATE478839T1 (https=) |
| AU (1) | AU2004249526B2 (https=) |
| CA (1) | CA2529018C (https=) |
| DE (1) | DE602004028830D1 (https=) |
| DK (1) | DK1646607T3 (https=) |
| ES (1) | ES2351662T3 (https=) |
| IT (1) | ITTO20030474A1 (https=) |
| PT (1) | PT1646607E (https=) |
| WO (1) | WO2004113271A2 (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7863330B2 (en) * | 2006-06-14 | 2011-01-04 | Rottapharm S.P.A. | Deloxiglumide and proton pump inhibitor combination in the treatment of gastrointestinal disorders |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1217123B (it) | 1987-02-05 | 1990-03-14 | Rotta Research Lab | Derivati otticamente attivi dell acido 5 pentilammino 5 oxo pentanoico r ad attivita antagonista della colecistochinina e procedimento per la loro preparazione |
| DE69112917T2 (de) * | 1990-06-15 | 1996-05-15 | Merck & Co Inc | Kristallisationsverfahren zur Verbesserung der Kristallstruktur und -grösse. |
| US7122083B2 (en) * | 2002-04-02 | 2006-10-17 | E. I. Du Pont De Nemours And Company | Apparatus and process used in growing crystals |
-
2003
- 2003-06-23 IT IT000474A patent/ITTO20030474A1/it unknown
-
2004
- 2004-06-21 CA CA2529018A patent/CA2529018C/en not_active Expired - Fee Related
- 2004-06-21 PT PT04743871T patent/PT1646607E/pt unknown
- 2004-06-21 AU AU2004249526A patent/AU2004249526B2/en not_active Ceased
- 2004-06-21 WO PCT/IB2004/002208 patent/WO2004113271A2/en not_active Ceased
- 2004-06-21 AT AT04743871T patent/ATE478839T1/de active
- 2004-06-21 EP EP04743871A patent/EP1646607B1/en not_active Expired - Lifetime
- 2004-06-21 ES ES04743871T patent/ES2351662T3/es not_active Expired - Lifetime
- 2004-06-21 DK DK04743871.8T patent/DK1646607T3/da active
- 2004-06-21 DE DE602004028830T patent/DE602004028830D1/de not_active Expired - Lifetime
- 2004-06-21 JP JP2006516595A patent/JP5197955B2/ja not_active Expired - Fee Related
- 2004-06-21 US US10/562,013 patent/US7662994B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| HK1089750A1 (en) | 2006-12-08 |
| EP1646607A2 (en) | 2006-04-19 |
| EP1646607B1 (en) | 2010-08-25 |
| ES2351662T3 (es) | 2011-02-09 |
| WO2004113271A2 (en) | 2004-12-29 |
| AU2004249526A1 (en) | 2004-12-29 |
| CA2529018A1 (en) | 2004-12-29 |
| AU2004249526B2 (en) | 2011-02-24 |
| PT1646607E (pt) | 2010-10-12 |
| DE602004028830D1 (de) | 2010-10-07 |
| WO2004113271A3 (en) | 2005-01-27 |
| CA2529018C (en) | 2013-05-28 |
| US7662994B2 (en) | 2010-02-16 |
| WO2004113271A8 (en) | 2005-05-06 |
| US20060154987A1 (en) | 2006-07-13 |
| ITTO20030474A1 (it) | 2004-12-24 |
| JP2007521253A (ja) | 2007-08-02 |
| DK1646607T3 (da) | 2010-11-22 |
| ATE478839T1 (de) | 2010-09-15 |
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