WO2007128721A1 - Polymorphe - Google Patents
Polymorphe Download PDFInfo
- Publication number
- WO2007128721A1 WO2007128721A1 PCT/EP2007/054201 EP2007054201W WO2007128721A1 WO 2007128721 A1 WO2007128721 A1 WO 2007128721A1 EP 2007054201 W EP2007054201 W EP 2007054201W WO 2007128721 A1 WO2007128721 A1 WO 2007128721A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- methyl
- polymorph
- xanthine
- butyn
- compound
- Prior art date
Links
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
- A61K31/52—Purines, e.g. adenine
- A61K31/522—Purines, e.g. adenine having oxo groups directly attached to the heterocyclic ring, e.g. hypoxanthine, guanine, acyclovir
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Definitions
- the invention relates to polymorphic crystal modifications of a DPP-IV inhibitor, their preparation and their use for the preparation of a medicament.
- DPP-IV also known as CD26
- CD26 is a serine protease that favors the cleavage of dipeptides in proteins with a proline or alanine residue at the N-terminal end.
- DPP-IV inhibitors thereby affect the plasma level of bioactive peptides including the peptide GLP-1.
- Compounds of this type are of interest for the prevention or treatment of diseases or conditions associated with increased DPP-IV activity or which can be prevented or alleviated by reduction of DPP-IV activity, in particular diabetes mellitus type I or type II, Prediabetes, or reduction of glucose tolerance.
- WO 2004/018468 describes DPP-IV inhibitors with valuable pharmacological properties.
- An example of the inhibitors disclosed therein is 1 - [(4-methylquinazolin-2-yl) methyl] -3-methyl-7- (2-butyn-1-yl) -8- (3- (R) -amino - piperidin-1-yl) -xanthine.
- polymorph A The pure high-temperature form (polymorph A), which can be obtained by heating the mixture to temperatures> 40 ° C, melts at 206 ⁇ 3 0 C.
- X-ray powder diagram (see Figure 3) shows this shape characteristic reflections at the following d values: 11.49 A, 7.60 A, 7.15 A, 3.86 A, 3.54 A, and 3.47 A (see also Tables 1 and 2).
- Anhydrous polymorph A can be prepared by adding
- the low-temperature form (polymorph B) is obtained by cooling to temperatures ⁇ 10 0 C.
- this shape shows characteristic reflections at the following d values: 11.25 A, 9.32 A, 7.46 A, 6.98 A and 3.77 A (see also Tables 3 and 4).
- Anhydrous polymorph B can be prepared by adding
- polymorph C in the X-ray powder diagram (see Figure 5) shows characteristic reflections at the following d values: 12.90 A, 11.10 A, 6.44 A, 3.93 A, and 3.74 A (see also Table 5).
- polymorph D melts at 150 ⁇ 3 ° C. This polymorph is obtained when polymorph C is heated to a temperature of 30-100 ° C or dried at this temperature.
- polymorph E which melts at a temperature of 175 ⁇ 3 0 C.
- Anhydrous polymorph E is formed when polymorph D is melted. Upon further heating Polymorph E crystallizes from the melt.
- polymorphs thus obtained can be used for the preparation of a medicament for the treatment of patients with diabetes mellitus type I and type II, prediabetes or diminished
- Glucose tolerance with rheumatoid arthritis, obesity, or calcitonin-induced osteoporosis, as well as patients undergoing allograft transplantation.
- These medicaments contain, in addition to one or more inert carriers, at least 0.1% to 0.5%, preferably at least 0.5% to 1.5% and more preferably at least 1% to 3% of one of the polymorphs A, B, or C. - A -
- Polymorph A melts at 206 ⁇ 3 0 C. In the DSC diagram, another weakly endothermic signal is observed at around 25 0 C. This is a fully reversible solid-solid phase transition between the two enantiotropic crystal modifications A and B. Form A is above this transition temperature, the thermodynamic stable modification, form B is below this transition temperature, the thermodynamic stable modification.
- Figure 2 shows a cyclic DSC diagram in which a total of 3 times over the phase transition from -40 0 C to 120 0 C and vice versa was passed away.
- the phase transition is observed as an endothermic signal, upon cooling accordingly as an exothermic signal.
- the phase transition can also be observed as an endothermic double signal or as a very broad signal, in all other cycles, the signal occurs as a very sharp endothermic or exothermic signal, depending on whether it is heated or cooled.
- Table 1 Indexed X-ray reflections up to 30 ° 2 ⁇ with intensities (normalized) for the anhydrous polymorph A
- Polymorph B is obtained by cooling the mold A from Example 1 to temperatures ⁇ 10 ° C.
- the suspension is a further 78 I tert. Butylmethylether added over 30 minutes and then stirred again at 45-55 ° C for 60 minutes, diluted to four times the volume. The suspension is slowly cooled to 15-25 0 C and stirred overnight at this temperature. After cooling the suspension to 0-5 0 C, the crystals are filtered off, washed with 2 portions of tert-butyl methyl ether and dried in a vacuum oven at 7O 0 C.
- Polymorph D obtained when Polymorph C of Example 3 heated to a temperature of 30-100 0 C and is dried at this temperature.
- Anhydrous polymorph E is formed when polymorph D is melted. Upon further heating Polymorph E crystallizes from the melt.
- An X-ray powder diagram was taken from an annealed at 100 C C sample shows another X-ray reflections as the starting material, which lead to the conclusion that it is in the form of C is a hydrate phase is with a stoichiometry somewhere in the range of a hemihydrate or monohydrate.
- the annealed sample is another anhydrous modification D, which is stable only under anhydrous conditions.
- the form D melts at about 150 0 C.
- anhydrous crystal modification E which melts on further heating at about 175 0 C.
- form A crystallizes from the melt of form E.
- Form E is also a metastable crystal modification that only occurs at high temperatures.
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Diabetes (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Obesity (AREA)
- Immunology (AREA)
- Hematology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Epidemiology (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Pain & Pain Management (AREA)
- Child & Adolescent Psychology (AREA)
- Transplantation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Steroid Compounds (AREA)
Abstract
Description
Claims
Priority Applications (15)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA2651089A CA2651089C (en) | 2006-05-04 | 2007-04-30 | A polymeric form of 1-((4-methyl-quinazolin-2-yl)methyl)-3-7-(2-butyn-1-yl)-8-(3-(r)-aminopiperidin-1-yl)xanthine |
KR1020087026976A KR101452915B1 (ko) | 2006-05-04 | 2007-04-30 | 다형태 |
NZ573360A NZ573360A (en) | 2006-05-04 | 2007-04-30 | Polymorphic forms of 1-[(4-methyl-quinazolin-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-(3-(R)-amino-piperidin-1-yl)-xanthine |
MX2008014024A MX2008014024A (es) | 2006-05-04 | 2007-04-30 | Formas poliformas. |
NO20190725A NO347644B1 (no) | 2006-05-04 | 2007-04-30 | Polymorfer |
EP07728655A EP2016079A1 (de) | 2006-05-04 | 2007-04-30 | Polymorphe |
AU2007247190A AU2007247190A1 (en) | 2006-05-04 | 2007-04-30 | Polymorphs |
UAA200813470A UA97244C2 (en) | 2006-05-04 | 2007-04-30 | Polymorphs of 1-((4-methyfquinazolin-2-yl)methyl)-3-methyl-7- (2-butyn-1-yl)-8-(3-(r)-aminopiperidin-l-yl)xanthine |
BRPI0711558-0A BRPI0711558A2 (pt) | 2006-05-04 | 2007-04-30 | polimorfos |
CN200780016135.5A CN101437823B (zh) | 2006-05-04 | 2007-04-30 | 多晶型 |
JP2009508325A JP5323684B2 (ja) | 2006-05-04 | 2007-04-30 | 多形体 |
EA200802198A EA015687B1 (ru) | 2006-05-04 | 2007-04-30 | Полиморфы |
NO20084359A NO20084359L (no) | 2006-05-04 | 2008-10-17 | Polymorfer |
IL195029A IL195029A (en) | 2006-05-04 | 2008-10-30 | Polymorphs |
HK09110600.2A HK1130494A1 (en) | 2006-05-04 | 2009-11-13 | Polymorphs |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP06009202.0 | 2006-05-04 | ||
EP06009202 | 2006-05-04 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2007128721A1 true WO2007128721A1 (de) | 2007-11-15 |
Family
ID=38335646
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2007/054201 WO2007128721A1 (de) | 2006-05-04 | 2007-04-30 | Polymorphe |
Country Status (24)
Country | Link |
---|---|
US (9) | US20070259900A1 (de) |
EP (2) | EP2016079A1 (de) |
JP (5) | JP5323684B2 (de) |
KR (2) | KR101541791B1 (de) |
CN (5) | CN102838599A (de) |
AR (1) | AR060756A1 (de) |
AU (1) | AU2007247190A1 (de) |
BR (1) | BRPI0711558A2 (de) |
CA (5) | CA2810295C (de) |
EA (2) | EA015687B1 (de) |
EC (1) | ECSP088794A (de) |
HK (3) | HK1130494A1 (de) |
IL (1) | IL195029A (de) |
MX (1) | MX2008014024A (de) |
MY (1) | MY158107A (de) |
NO (2) | NO347644B1 (de) |
NZ (3) | NZ600394A (de) |
PE (1) | PE20080088A1 (de) |
SG (1) | SG174054A1 (de) |
TW (2) | TWI534147B (de) |
UA (1) | UA97244C2 (de) |
UY (1) | UY30320A1 (de) |
WO (1) | WO2007128721A1 (de) |
ZA (1) | ZA200808224B (de) |
Cited By (65)
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WO2009024542A2 (en) * | 2007-08-17 | 2009-02-26 | Boehringer Ingelheim International Gmbh | Purin derivatives for use in the treatment of fab-related diseases |
WO2010072776A1 (en) | 2008-12-23 | 2010-07-01 | Boehringer Ingelheim International Gmbh | Salt forms of organic compound |
WO2010079197A1 (en) | 2009-01-07 | 2010-07-15 | Boehringer Ingelheim International Gmbh | Treatment of diabetes in patients with inadequate glycemic control despite metformin therapy comprising a dpp-iv inhibitor |
WO2010086411A1 (en) | 2009-01-29 | 2010-08-05 | Boehringer Ingelheim International Gmbh | Dpp-iv inhibitors for treatment of diabetes in paediatric patients |
WO2010092124A1 (en) | 2009-02-13 | 2010-08-19 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition comprising linagliptin and optionally a sglt2 inhibitor, and uses thereof |
WO2010092125A1 (en) | 2009-02-13 | 2010-08-19 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition comprising a sglt2 inhibitor, a dpp-iv inhibitor and optionally a further antidiabetic agent and uses thereof |
WO2010092163A2 (en) | 2009-02-13 | 2010-08-19 | Boehringer Ingelheim International Gmbh | Antidiabetic medications |
US7820815B2 (en) | 2004-11-05 | 2010-10-26 | Boehringer Ingelheim International Gmbh | Process for the preparation of chiral 8-(-3-aminopiperidin-1-yl) xanthines |
WO2011005929A1 (en) | 2009-07-09 | 2011-01-13 | Arena Pharmaceuticals, Inc. | Piperidine derivative and its use for the treatment of diabets and obesity |
WO2011039367A2 (en) | 2009-10-02 | 2011-04-07 | Boehringer Ingelheim International Gmbh | Therapeutic uses of pharmaceutical compositions |
WO2011064352A1 (en) | 2009-11-27 | 2011-06-03 | Boehringer Ingelheim International Gmbh | Treatment of genotyped diabetic patients with dpp-iv inhibitors such as linagliptin |
WO2011113947A1 (en) | 2010-03-18 | 2011-09-22 | Boehringer Ingelheim International Gmbh | Combination of a gpr119 agonist and the dpp-iv inhibitor linagliptin for use in the treatment of diabetes and related conditions |
WO2011127051A1 (en) | 2010-04-06 | 2011-10-13 | Arena Pharmaceuticals, Inc. | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
WO2011138421A1 (en) | 2010-05-05 | 2011-11-10 | Boehringer Ingelheim International Gmbh | Combination therapy |
WO2011138380A1 (en) | 2010-05-05 | 2011-11-10 | Boehringer Ingelheim International Gmbh | Pharmaceutical formulations comprising pioglitazone and linagliptin |
WO2011161161A1 (en) | 2010-06-24 | 2011-12-29 | Boehringer Ingelheim International Gmbh | Diabetes therapy |
US8106060B2 (en) | 2005-07-30 | 2012-01-31 | Boehringer Ingelheim International Gmbh | 8-(3-amino-piperidin-1-yl)-xanthines, their preparation, and their use as pharmaceuticals |
US8119648B2 (en) | 2002-08-21 | 2012-02-21 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | 8-[3-amino-piperidin-1-yl]-xanthines, the preparation thereof and their use as pharmaceutical compositions |
WO2012040279A1 (en) | 2010-09-22 | 2012-03-29 | Arena Pharmaceuticals, Inc. | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
WO2012065993A1 (en) | 2010-11-15 | 2012-05-24 | Boehringer Ingelheim International Gmbh | Vasoprotective and cardioprotective antidiabetic therapy |
US8232281B2 (en) | 2006-05-04 | 2012-07-31 | Boehringer Ingelheim International Gmbh | Uses of DPP-IV inhibitors |
WO2012120040A1 (en) | 2011-03-07 | 2012-09-13 | Boehringer Ingelheim International Gmbh | Pharmaceutical compositions comprising metformin and a dpp-4 inhibitor or a sglt-2 inhibitor |
WO2012135570A1 (en) | 2011-04-01 | 2012-10-04 | Arena Pharmaceuticals, Inc. | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
WO2012145604A1 (en) | 2011-04-22 | 2012-10-26 | Arena Pharmaceuticals, Inc. | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
WO2012145361A1 (en) | 2011-04-19 | 2012-10-26 | Arena Pharmaceuticals, Inc. | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
WO2012145603A1 (en) | 2011-04-22 | 2012-10-26 | Arena Pharmaceuticals, Inc. | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
WO2012152837A1 (en) | 2011-05-10 | 2012-11-15 | Sandoz Ag | Polymorph of linagliptin benzoate |
WO2012170702A1 (en) | 2011-06-08 | 2012-12-13 | Arena Pharmaceuticals, Inc. | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
WO2013055910A1 (en) | 2011-10-12 | 2013-04-18 | Arena Pharmaceuticals, Inc. | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
ITMI20112053A1 (it) * | 2011-11-11 | 2013-05-12 | Dipharma Francis Srl | Forma amorfa di un inibitore enzimatico |
WO2013074817A1 (en) | 2011-11-16 | 2013-05-23 | Assia Chemical Industries Ltd. | Solid state forms of linagliptin |
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US8513264B2 (en) | 2008-09-10 | 2013-08-20 | Boehringer Ingelheim International Gmbh | Combination therapy for the treatment of diabetes and related conditions |
WO2013128379A2 (en) * | 2012-02-27 | 2013-09-06 | Dr. Reddy's Laboratories Limited | Crystalline polymorphic forms of linagliptin |
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US8551957B2 (en) | 2007-08-16 | 2013-10-08 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition comprising a glucopyranosyl-substituted benzene derivate |
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- 2008-11-04 MY MYPI20084415A patent/MY158107A/en unknown
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2009
- 2009-11-13 HK HK09110600.2A patent/HK1130494A1/xx unknown
- 2009-11-13 HK HK15100613.0A patent/HK1200132A1/xx unknown
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2012
- 2012-08-01 US US13/563,767 patent/US20120296091A1/en not_active Abandoned
- 2012-08-15 JP JP2012180151A patent/JP5800773B2/ja active Active
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2014
- 2014-08-18 JP JP2014165973A patent/JP6022513B2/ja active Active
- 2014-08-19 US US14/462,654 patent/US9266888B2/en active Active
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2016
- 2016-01-13 US US14/994,578 patent/US9493462B2/en active Active
- 2016-10-05 JP JP2016197147A patent/JP6309589B2/ja active Active
- 2016-10-05 US US15/285,871 patent/US9815837B2/en active Active
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2017
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2018
- 2018-03-14 JP JP2018046434A patent/JP6602909B2/ja active Active
- 2018-04-10 HK HK18104664.7A patent/HK1245264A1/zh unknown
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2019
- 2019-04-03 US US16/373,971 patent/US20190233423A1/en not_active Abandoned
- 2019-10-24 US US16/662,406 patent/US11084819B2/en active Active
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2021
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