AU2004249526B2 - A method for the preparation of crystalline dexloxiglumide - Google Patents
A method for the preparation of crystalline dexloxiglumide Download PDFInfo
- Publication number
- AU2004249526B2 AU2004249526B2 AU2004249526A AU2004249526A AU2004249526B2 AU 2004249526 B2 AU2004249526 B2 AU 2004249526B2 AU 2004249526 A AU2004249526 A AU 2004249526A AU 2004249526 A AU2004249526 A AU 2004249526A AU 2004249526 B2 AU2004249526 B2 AU 2004249526B2
- Authority
- AU
- Australia
- Prior art keywords
- dexloxiglumide
- crystalline
- less
- particle size
- solvent
- 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.)
- Ceased
Links
- 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 title claims abstract description 37
- 229950010525 dexloxiglumide Drugs 0.000 title claims abstract description 36
- 238000000034 method Methods 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 238000002425 crystallisation Methods 0.000 claims abstract description 20
- 230000008025 crystallization Effects 0.000 claims abstract description 18
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000002245 particle Substances 0.000 claims description 32
- 238000009826 distribution Methods 0.000 claims description 18
- 239000000843 powder Substances 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 14
- 238000010899 nucleation Methods 0.000 claims description 13
- 239000000463 material Substances 0.000 claims description 10
- 239000012043 crude product Substances 0.000 claims description 8
- 238000000691 measurement method Methods 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 239000010419 fine particle Substances 0.000 claims description 6
- 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
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 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
- 229920000168 Microcrystalline cellulose Polymers 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- -1 disaggregants Substances 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 239000005414 inactive 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
- XUIMIQQOPSSXEZ-NJFSPNSNSA-N silicon-30 atom Chemical compound [30Si] XUIMIQQOPSSXEZ-NJFSPNSNSA-N 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 238000000746 purification Methods 0.000 abstract description 4
- 230000000877 morphologic effect Effects 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 12
- 239000013078 crystal Substances 0.000 description 9
- 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
- 230000000704 physical effect Effects 0.000 description 3
- 102100025841 Cholecystokinin Human genes 0.000 description 2
- 101800001982 Cholecystokinin Proteins 0.000 description 2
- 230000002902 bimodal effect Effects 0.000 description 2
- 229940107137 cholecystokinin Drugs 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
- 238000003921 particle size analysis Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 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 2
- 206010004663 Biliary colic Diseases 0.000 description 1
- 208000017228 Gastrointestinal motility disease Diseases 0.000 description 1
- 206010033645 Pancreatitis Diseases 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 230000035508 accumulation Effects 0.000 description 1
- 238000009825 accumulation Methods 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
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000007922 dissolution test Methods 0.000 description 1
- 201000006549 dyspepsia Diseases 0.000 description 1
- 230000000694 effects Effects 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
- 230000002349 favourable effect Effects 0.000 description 1
- 238000009472 formulation Methods 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
- 230000001788 irregular Effects 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
- 238000002356 laser light scattering Methods 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
- 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
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
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 (2)
| Publication Number | Publication Date |
|---|---|
| AU2004249526A1 AU2004249526A1 (en) | 2004-12-29 |
| AU2004249526B2 true AU2004249526B2 (en) | 2011-02-24 |
Family
ID=33524063
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2004249526A Ceased AU2004249526B2 (en) | 2003-06-23 | 2004-06-21 | A method for the preparation of crystalline dexloxiglumide |
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 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5602179A (en) * | 1987-02-05 | 1997-02-11 | Rotta Research Laboratorium S.P.A. | Optically-active derivatives of (R) 5-pentylamino-5-oxopentanoic acid with antagonistic activity towards cholecystokinin and a method for their preparation |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5602179A (en) * | 1987-02-05 | 1997-02-11 | Rotta Research Laboratorium S.P.A. | Optically-active derivatives of (R) 5-pentylamino-5-oxopentanoic acid with antagonistic activity towards cholecystokinin and a method for their preparation |
Non-Patent Citations (8)
| Title |
|---|
| CHEMICAL ABSTRACTS ACCESSION NO. 1996: 398396 ABSTRACT & SCARPIGNATO, C. et al. ALIMENT PHARMACOL THER, 1996, 10(3), pages 411-419. * |
| CHEMICAL ABSTRACTS ACCESSION NO. 1998:370098 ABSTRACT & VARGA, G. et al. BRITISH JOURNAL OF PHARMACOLOGY, 1998, 124(3), pages 435-440. * |
| CHEMICAL ABSTRACTS ACCESSION NO. 1999:656782 ABSTRACT & REVEL, L. et al: "Dexloxiglumide: CCK1 (CCKA) Receptor Antagonist Treatment of Irritable Bowel Syndrome". DRUGS OF THE FUTURE, 1999, 24(7), pages 725-728. * |
| CHEMICAL ABSTRACTS ACCESSION NO. 2002:485631 ABSTRACT & PERSIANI, S et al. INTERNATIONAL JOURNAL OF CLINICAL PHARMACOLOGY AND THERAPEUTICS, 2002, 4(5), pages 198-206. * |
| CHEMICAL ABSTRACTS ACCESSION NO. 2002:50662 ABSTRACT & MASELLI, M. A. et al: "Effect of Three Nonpeptide Cholecystokinin Antagonists on Human isolated Gallbladder". DIGESTIVE DISEASES AND SCIENCES, 2001, 46(12), pages 2773-2778. * |
| CHEMICAL ABSTRACTS ACCESSION NO. 2002:577063 ABSTRACT & FRIED, M et al: "The role of fat and cholecystokinin in fuctional dyspepsia". GUT, 2002, 51(SUPPL. 1), pages i54-i57. * |
| CHEMICAL ABSTRACTS ACCESSION NO. 2002:580010 ABSTRACT & VARGA, G: "Dexloxiglumide". ROTTA RESEARCH, CURRENT OPINION ON INVESTIGATIONAL DRUGS, 2002, 3(4), pages 621-626. * |
| CHEMICAL ABSTRACTS ACCESSION NO. 2002:580170 ABSTRACT & KATSCHINSKI, M: "Loxiglumide". ROTTA RESEARCH, IDRUGS, 2002, 5(5), pages 469-474. * |
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 |
| 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 |
| JP5197955B2 (ja) | 2013-05-15 |
| ATE478839T1 (de) | 2010-09-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) | ||
| PC | Assignment registered |
Owner name: ROTTAPHARM BIOTECH S.R.L. Free format text: FORMER OWNER WAS: ROTTAPHARM S.P.A. |
|
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |