EP2016079A1 - Polymorphes - Google Patents
PolymorphesInfo
- Publication number
- EP2016079A1 EP2016079A1 EP07728655A EP07728655A EP2016079A1 EP 2016079 A1 EP2016079 A1 EP 2016079A1 EP 07728655 A EP07728655 A EP 07728655A EP 07728655 A EP07728655 A EP 07728655A EP 2016079 A1 EP2016079 A1 EP 2016079A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- methyl
- polymorph
- xanthine
- butyn
- compound
- 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.)
- Withdrawn
Links
Classifications
-
- 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
-
- 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
-
- 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.
Abstract
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP12185396A EP2540725A1 (fr) | 2006-05-04 | 2007-04-30 | Polymorphes de 1-((4-Methyl-chinazolin-2-yl)methyl)-3-methyl-7-(2-butin-1-yl)-8-(3-(R)-amino-piperidin-1-yl)xanthin |
EP07728655A EP2016079A1 (fr) | 2006-05-04 | 2007-04-30 | Polymorphes |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP06009202 | 2006-05-04 | ||
PCT/EP2007/054201 WO2007128721A1 (fr) | 2006-05-04 | 2007-04-30 | Polymorphes |
EP07728655A EP2016079A1 (fr) | 2006-05-04 | 2007-04-30 | Polymorphes |
Publications (1)
Publication Number | Publication Date |
---|---|
EP2016079A1 true EP2016079A1 (fr) | 2009-01-21 |
Family
ID=38335646
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP12185396A Withdrawn EP2540725A1 (fr) | 2006-05-04 | 2007-04-30 | Polymorphes de 1-((4-Methyl-chinazolin-2-yl)methyl)-3-methyl-7-(2-butin-1-yl)-8-(3-(R)-amino-piperidin-1-yl)xanthin |
EP07728655A Withdrawn EP2016079A1 (fr) | 2006-05-04 | 2007-04-30 | Polymorphes |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP12185396A Withdrawn EP2540725A1 (fr) | 2006-05-04 | 2007-04-30 | Polymorphes de 1-((4-Methyl-chinazolin-2-yl)methyl)-3-methyl-7-(2-butin-1-yl)-8-(3-(R)-amino-piperidin-1-yl)xanthin |
Country Status (24)
Country | Link |
---|---|
US (9) | US20070259900A1 (fr) |
EP (2) | EP2540725A1 (fr) |
JP (5) | JP5323684B2 (fr) |
KR (2) | KR101541791B1 (fr) |
CN (5) | CN102838599A (fr) |
AR (1) | AR060756A1 (fr) |
AU (1) | AU2007247190A1 (fr) |
BR (1) | BRPI0711558A2 (fr) |
CA (5) | CA2810295C (fr) |
EA (2) | EA030606B1 (fr) |
EC (1) | ECSP088794A (fr) |
HK (3) | HK1130494A1 (fr) |
IL (1) | IL195029A (fr) |
MX (1) | MX2008014024A (fr) |
MY (1) | MY158107A (fr) |
NO (2) | NO347644B1 (fr) |
NZ (3) | NZ600394A (fr) |
PE (1) | PE20080088A1 (fr) |
SG (1) | SG174054A1 (fr) |
TW (2) | TWI396539B (fr) |
UA (1) | UA97244C2 (fr) |
UY (1) | UY30320A1 (fr) |
WO (1) | WO2007128721A1 (fr) |
ZA (1) | ZA200808224B (fr) |
Families Citing this family (107)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7407955B2 (en) | 2002-08-21 | 2008-08-05 | Boehringer Ingelheim Pharma Gmbh & Co., Kg | 8-[3-amino-piperidin-1-yl]-xanthines, the preparation thereof and their use as pharmaceutical compositions |
US7495005B2 (en) | 2002-08-22 | 2009-02-24 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Xanthine derivatives, their preparation and their use in pharmaceutical compositions |
US7482337B2 (en) | 2002-11-08 | 2009-01-27 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Xanthine derivatives, the preparation thereof and their use as pharmaceutical compositions |
DE10254304A1 (de) | 2002-11-21 | 2004-06-03 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Xanthinderivate, deren Herstellung und deren Verwendung als Arzneimittel |
US7501426B2 (en) | 2004-02-18 | 2009-03-10 | Boehringer Ingelheim International Gmbh | 8-[3-amino-piperidin-1-yl]-xanthines, their preparation and their use as pharmaceutical compositions |
DE102004009039A1 (de) | 2004-02-23 | 2005-09-08 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | 8-[3-Amino-piperidin-1-yl]-xanthine, deren Herstellung und Verwendung als Arzneimittel |
US7179809B2 (en) * | 2004-04-10 | 2007-02-20 | Boehringer Ingelheim International Gmbh | 2-Amino-imidazo[4,5-d]pyridazin-4-ones, their preparation and their use as pharmaceutical compositions |
US7439370B2 (en) | 2004-05-10 | 2008-10-21 | Boehringer Ingelheim International Gmbh | Imidazole derivatives, their preparation and their use as intermediates for the preparation of pharmaceutical compositions and pesticides |
DE102004030502A1 (de) | 2004-06-24 | 2006-01-12 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Imidazole und Triazole, deren Herstellung und Verwendung als Arzneimittel |
US20060035903A1 (en) * | 2004-08-14 | 2006-02-16 | Boehringer Ingelheim International Gmbh | Storage stable perfusion solution for dihydropteridinones |
US20060058311A1 (en) | 2004-08-14 | 2006-03-16 | Boehringer Ingelheim International Gmbh | Combinations for the treatment of diseases involving cell proliferation |
DE102004043944A1 (de) * | 2004-09-11 | 2006-03-30 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue 8-(3-Amino-piperidin-1-yl)-7-(but-2-inyl)-xanthine, deren Herstellung und deren Verwendung als Arzneimittel |
DE102004044221A1 (de) | 2004-09-14 | 2006-03-16 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue 3-Methyl-7-butinyl-xanthine, deren Herstellung und deren Verwendung als Arzneimittel |
DE102004054054A1 (de) | 2004-11-05 | 2006-05-11 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Verfahren zur Herstellung chiraler 8-(3-Amino-piperidin-1-yl)-xanthine |
DE102005035891A1 (de) | 2005-07-30 | 2007-02-08 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | 8-(3-Amino-piperidin-1-yl)-xanthine, deren Herstellung und deren Verwendung als Arzneimittel |
US7439358B2 (en) | 2006-02-08 | 2008-10-21 | Boehringer Ingelheim International Gmbh | Specific salt, anhydrous and crystalline form of a dihydropteridione derivative |
PE20080251A1 (es) | 2006-05-04 | 2008-04-25 | Boehringer Ingelheim Int | Usos de inhibidores de dpp iv |
EA030606B1 (ru) * | 2006-05-04 | 2018-08-31 | Бёрингер Ингельхайм Интернациональ Гмбх | Способы приготовления лекарственного средства, содержащего полиморфы |
EP1852108A1 (fr) | 2006-05-04 | 2007-11-07 | Boehringer Ingelheim Pharma GmbH & Co.KG | Compositions d'inhibiteurs de la DPP IV |
EP2057160A1 (fr) | 2006-08-08 | 2009-05-13 | Boehringer Ingelheim International GmbH | Pyrrolo [3,2-d]pyrimidines utilisees en tant qu'inhibiteurs de dpp-iv pour le traitement du diabete sucre |
EP2025674A1 (fr) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Tetrahydronaphthaline substituée, son procédé de fabrication et son utilisation en tant que médicament |
CL2008002427A1 (es) | 2007-08-16 | 2009-09-11 | Boehringer Ingelheim Int | Composicion farmaceutica que comprende 1-cloro-4-(b-d-glucopiranos-1-il)-2-[4-((s)-tetrahidrofurano-3-iloxi)bencil]-benceno combinado con 1-[(4-metilquinazolin-2-il)metil]-3-metil-7-(2-butin-1-il)-8-(3-(r)-aminopiperidin-1-il)xantina; y su uso para tratar diabetes mellitus tipo 2. |
KR101610005B1 (ko) * | 2007-08-17 | 2016-04-08 | 베링거 인겔하임 인터내셔날 게엠베하 | Fab 관련 질환의 치료에 사용하기 위한 푸린 유도체 |
EP2242745A1 (fr) * | 2008-02-07 | 2010-10-27 | Sanofi-Aventis | Nouvelles imidazolidines substituées par un phényle, procédé de production, médicaments contenant ces composés et leur utilisation |
PE20140960A1 (es) | 2008-04-03 | 2014-08-15 | Boehringer Ingelheim Int | Formulaciones que comprenden un inhibidor de dpp4 |
UY32030A (es) | 2008-08-06 | 2010-03-26 | Boehringer Ingelheim Int | "tratamiento para diabetes en pacientes inapropiados para terapia con metformina" |
BRPI0916997A2 (pt) | 2008-08-06 | 2020-12-15 | Boehringer Ingelheim International Gmbh | Inibidor de dpp-4 e seu uso |
EA031225B1 (ru) | 2008-08-15 | 2018-12-28 | Бёрингер Ингельхайм Интернациональ Гмбх | Ингибиторы дпп-4 для заживления ран |
EP2344195A2 (fr) | 2008-09-10 | 2011-07-20 | Boehringer Ingelheim International GmbH | Polythérapie pour le traitement du diabète et des états pathologiques apparentés |
US20200155558A1 (en) | 2018-11-20 | 2020-05-21 | Boehringer Ingelheim International Gmbh | Treatment for diabetes in patients with insufficient glycemic control despite therapy with an oral antidiabetic drug |
BRPI0923121A2 (pt) * | 2008-12-23 | 2015-08-11 | Boehringer Ingelheim Int | Formas salinas de compostos orgânico |
TW201036975A (en) | 2009-01-07 | 2010-10-16 | Boehringer Ingelheim Int | Treatment for diabetes in patients with inadequate glycemic control despite metformin therapy |
AR075204A1 (es) | 2009-01-29 | 2011-03-16 | Boehringer Ingelheim Int | Inhibidores de dpp-4 y composiciones farmaceuticas que los comprenden, utiles para tratar enfermedades metabolicas en pacientes pediatricos, particularmente diabetes mellitus tipo 2 |
JP2012517977A (ja) | 2009-02-13 | 2012-08-09 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Dpp−4阻害剤(リナグリプチン)を任意で他の抗糖尿病薬と組み合わせて含む抗糖尿病薬 |
UY32427A (es) | 2009-02-13 | 2010-09-30 | Boheringer Ingelheim Internat Gmbh | Composicion farmaceutica, forma farmaceutica, procedimiento para su preparacion, metodos de tratamiento y usos de la misma |
JP5685550B2 (ja) | 2009-02-13 | 2015-03-18 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Sglt2阻害剤、dpp−iv阻害剤、更に必要により抗糖尿病薬を含む医薬組成物及びその使用 |
AR077642A1 (es) | 2009-07-09 | 2011-09-14 | Arena Pharm Inc | Moduladores del metabolismo y el tratamiento de trastornos relacionados con el mismo |
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EP2582709B1 (fr) | 2010-06-18 | 2018-01-24 | Sanofi | Dérivés d'azolopyridin-3-one en tant qu'inhibiteurs de lipases et de phospholipases |
US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
EA201991014A1 (ru) | 2010-06-24 | 2019-09-30 | Бёрингер Ингельхайм Интернациональ Гмбх | Лечение диабета |
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SG188548A1 (en) | 2010-09-22 | 2013-04-30 | Arena Pharm Inc | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
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US9034883B2 (en) | 2010-11-15 | 2015-05-19 | Boehringer Ingelheim International Gmbh | Vasoprotective and cardioprotective antidiabetic therapy |
US9358233B2 (en) | 2010-11-29 | 2016-06-07 | Boehringer Ingelheim International Gmbh | Method for treating acute myeloid leukemia |
UY33937A (es) | 2011-03-07 | 2012-09-28 | Boehringer Ingelheim Int | Composiciones farmacéuticas que contienen inhibidores de dpp-4 y/o sglt-2 y metformina |
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WO2004018468A2 (fr) | 2002-08-21 | 2004-03-04 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | 8-[3-amino-piperidin-1-yl]-xanthines, leur production et leur utilisation comme medicament |
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