US20070259900A1 - Polymorphs - Google Patents
Polymorphs Download PDFInfo
- Publication number
- US20070259900A1 US20070259900A1 US11/744,700 US74470007A US2007259900A1 US 20070259900 A1 US20070259900 A1 US 20070259900A1 US 74470007 A US74470007 A US 74470007A US 2007259900 A1 US2007259900 A1 US 2007259900A1
- Authority
- US
- United States
- Prior art keywords
- methyl
- polymorph
- butyn
- quinazolin
- xanthine
- 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.)
- Abandoned
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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
-
- 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 polymorphous crystal modifications of a DPP-IV inhibitor, the preparation thereof and the use thereof for preparing a medicament.
- the enzyme DPP-IV also known by the name CD26, is a serine protease which promotes the cleaving of dipeptides in proteins with a proline or alanine group at the N-terminal end. DPP-IV inhibitors thereby influence the plasma level of bioactive peptides including the peptide GLP-1.
- Compounds of this type are useful for the prevention or treatment of illnesses or conditions which are associated with an increased DPP-IV activity or which can be prevented or alleviated by reducing the DPP-IV activity, particularly type I or type II diabetes mellitus, prediabetes, or reduced glucose tolerance.
- WO 2004/018468 describes DPP-IV inhibitors with valuable pharmacological properties.
- One example of the inhibitors disclosed therein is 1-[(4-methyl-quinazolin-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-(3-(R)-amino-piperidin-1-yl)-xanthine.
- FIG. 1 shows the thermoanalysis of the anhydrous form A/B.
- FIG. 2 shows a cyclic DSC diagram, in which the phase transition from ⁇ 40° C. to 120° C. and vice versa has been run through a total of 3 times.
- FIG. 3 shows an X-ray powder diagram of the anhydrous form A.
- FIG. 4 shows an X-ray powder diagram of the anhydrous form B.
- FIG. 5 shows an X-ray powder diagram of polymorph C.
- FIG. 6 shows the thermoanalysis of form C.
- 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° C.
- this form shows characteristic reflexes at the following d values: 11.49 ⁇ , 7.60 ⁇ , 7.15 ⁇ , 3.86 ⁇ , 3.54 ⁇ and 3.47 ⁇ (cf. also Table 1 and 2).
- Anhydrous polymorph A may be prepared by
- the low temperature form (polymorph B) is obtained by cooling to temperatures ⁇ 10° C.
- this form shows characteristic reflexes at the following d values: 11.25 ⁇ , 9.32 ⁇ , 7.46 ⁇ , 6.98 ⁇ and 3.77 ⁇ (cf. also Table 3 and 4).
- Anhydrous polymorph B may be prepared by
- polymorph C shows characteristic reflexes in the X-ray powder diagram (see FIG. 5 ) at the following d values: 12.90 ⁇ , 11.10 ⁇ , 6.44 ⁇ , 3.93 ⁇ and 3.74 ⁇ (cf. also Table 5).
- polymorph D melts at 150 ⁇ 3° C. This polymorph is obtained if 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° C. Anhydrous polymorph E is formed if polymorph D is melted. On further heating, polymorph E crystallises out of the melt.
- the polymorphs thus obtained may be used in the same way as the mixture of the two polymorphs A and B described in WO 2004/018468 for preparing a pharmaceutical composition which is suitable for treating patients with type I and type II diabetes mellitus, prediabetes or reduced glucose tolerance, with rheumatoid arthritis, obesity, or calcitonin-induced osteoporosis, as well as patients in whom an allograft transplant has been carried out.
- 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 particularly preferably at least 1% to 3% of one of the polymorphs A, B, or C.
- FIG. 1 shows the thermoanalysis of the anhydrous form A/B.
- Plymorph A melts at 206 ⁇ 3° C. In the DSC diagram another slightly endothermic signal can be seen at approx. 25° C. This is a fully reversible solid-solid phase transition between the two enantiotropic crystal modifications A and B.
- the form A is the thermodynamically stable modification above this transformation temperature
- form B is the thermodynamically stable modification below this transformation temperature.
- FIG. 2 shows a cyclic DSC diagram, in which the phase transition from ⁇ 40° C. to 120° C. and vice versa has been run through a total of 3 times.
- the phase transition is observed as an endothermic signal and, correspondingly, during cooling it is observed as an exothermic signal.
- the phase transition may also be observed as an endothermic double signal or as a very broad signal while in all the other cycles the signal occurs as a very sharp endothermic or exothermic signal, depending on whether heating or cooling is taking place.
- FIG. 3 shows an X-ray powder diagram of the anhydrous form A
- Polymorph B is obtained by cooling form A from Example 1 to temperatures ⁇ 10° C.
- FIG. 4 shows an X-ray powder diagram of the anhydrous form B
- a further 78 l tert. butylmethylether are added to the suspension over 30 minutes and then it is stirred again for a further 60 minutes at 45-55° C. It is diluted to four times the volume. The suspension is slowly cooled to 15-25° C. and stirred overnight at this temperature. After the suspension has been cooled to 0-5° C. the crystals are suction filtered, washed with 2 batches tert.-butylmethylether and dried at 70° C. in the vacuum dryer.
- FIG. 5 shows an X-ray powder diagram of polymorph C
- Polymorph D is obtained if polymorph C from Example 3 is heated to a temperature of 30-100° C. or dried at this temperature.
- Anhydrous polymorph E is obtained if polymorph D is melted. On further heating, polymorph E crystallises out of the melt.
- FIG. 6 shows a thermoanalysis of form C
- An X-ray powder diagram taken of a sample maintained at a temperature of 100° C. shows different X-ray reflexes from the starting material, suggesting that form C is a hydrate phase with stoichiometry somewhere in the region of a hemihydrate or monohydrate.
- the temperature-controlled sample is another anhydrous modification D, which only stable under anhydrous conditions.
- the D form melts at approx. 150° C.
- Another anhydrous crystal modification E crystallises from the melt, and when heated further melts at approx. 175° C.
- form A crystallises from the melt of form E is also a metastable crystal modification which occurs only at high temperatures.
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Physical Education & Sports Medicine (AREA)
- Hematology (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Obesity (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Pain & Pain Management (AREA)
- Child & Adolescent Psychology (AREA)
- Transplantation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Steroid Compounds (AREA)
- Medicinal Preparation (AREA)
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US13/563,767 US20120296091A1 (en) | 2006-05-04 | 2012-08-01 | Polymorphs |
US14/462,654 US9266888B2 (en) | 2006-05-04 | 2014-08-19 | Polymorphs |
US14/994,578 US9493462B2 (en) | 2006-05-04 | 2016-01-13 | Polymorphs |
US15/285,871 US9815837B2 (en) | 2006-05-04 | 2016-10-05 | Polymorphs |
US15/725,426 US10301313B2 (en) | 2006-05-04 | 2017-10-05 | Polymorphs |
US16/373,971 US20190233423A1 (en) | 2006-05-04 | 2019-04-03 | Polymorphs |
US16/662,406 US11084819B2 (en) | 2006-05-04 | 2019-10-24 | Polymorphs |
US17/363,441 US11919903B2 (en) | 2006-05-04 | 2021-06-30 | Polymorphs |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP06009202 | 2006-05-04 | ||
EP06009202 | 2006-05-04 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US13/563,767 Continuation US20120296091A1 (en) | 2006-05-04 | 2012-08-01 | Polymorphs |
Publications (1)
Publication Number | Publication Date |
---|---|
US20070259900A1 true US20070259900A1 (en) | 2007-11-08 |
Family
ID=38335646
Family Applications (9)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US11/744,700 Abandoned US20070259900A1 (en) | 2006-05-04 | 2007-05-04 | Polymorphs |
US13/563,767 Abandoned US20120296091A1 (en) | 2006-05-04 | 2012-08-01 | Polymorphs |
US14/462,654 Active 2027-05-25 US9266888B2 (en) | 2006-05-04 | 2014-08-19 | Polymorphs |
US14/994,578 Active 2027-05-06 US9493462B2 (en) | 2006-05-04 | 2016-01-13 | Polymorphs |
US15/285,871 Active US9815837B2 (en) | 2006-05-04 | 2016-10-05 | Polymorphs |
US15/725,426 Active US10301313B2 (en) | 2006-05-04 | 2017-10-05 | Polymorphs |
US16/373,971 Abandoned US20190233423A1 (en) | 2006-05-04 | 2019-04-03 | Polymorphs |
US16/662,406 Active US11084819B2 (en) | 2006-05-04 | 2019-10-24 | Polymorphs |
US17/363,441 Active 2027-05-20 US11919903B2 (en) | 2006-05-04 | 2021-06-30 | Polymorphs |
Family Applications After (8)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US13/563,767 Abandoned US20120296091A1 (en) | 2006-05-04 | 2012-08-01 | Polymorphs |
US14/462,654 Active 2027-05-25 US9266888B2 (en) | 2006-05-04 | 2014-08-19 | Polymorphs |
US14/994,578 Active 2027-05-06 US9493462B2 (en) | 2006-05-04 | 2016-01-13 | Polymorphs |
US15/285,871 Active US9815837B2 (en) | 2006-05-04 | 2016-10-05 | Polymorphs |
US15/725,426 Active US10301313B2 (en) | 2006-05-04 | 2017-10-05 | Polymorphs |
US16/373,971 Abandoned US20190233423A1 (en) | 2006-05-04 | 2019-04-03 | Polymorphs |
US16/662,406 Active US11084819B2 (en) | 2006-05-04 | 2019-10-24 | Polymorphs |
US17/363,441 Active 2027-05-20 US11919903B2 (en) | 2006-05-04 | 2021-06-30 | Polymorphs |
Country Status (24)
Country | Link |
---|---|
US (9) | US20070259900A1 (ru) |
EP (2) | EP2016079A1 (ru) |
JP (5) | JP5323684B2 (ru) |
KR (2) | KR101452915B1 (ru) |
CN (5) | CN102838599A (ru) |
AR (1) | AR060756A1 (ru) |
AU (1) | AU2007247190A1 (ru) |
BR (1) | BRPI0711558A2 (ru) |
CA (5) | CA2810522A1 (ru) |
EA (2) | EA030606B1 (ru) |
EC (1) | ECSP088794A (ru) |
HK (3) | HK1200132A1 (ru) |
IL (1) | IL195029A (ru) |
MX (1) | MX2008014024A (ru) |
MY (1) | MY158107A (ru) |
NO (2) | NO347644B1 (ru) |
NZ (3) | NZ573360A (ru) |
PE (1) | PE20080088A1 (ru) |
SG (1) | SG174054A1 (ru) |
TW (2) | TWI396539B (ru) |
UA (1) | UA97244C2 (ru) |
UY (1) | UY30320A1 (ru) |
WO (1) | WO2007128721A1 (ru) |
ZA (1) | ZA200808224B (ru) |
Cited By (56)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20060058323A1 (en) * | 2004-09-11 | 2006-03-16 | Boehringer Ingelheim International Gmbh | New 8-(3-amino-piperidin-1-yl)-7-(but-2-ynyl)-xanthines, the preparation thereof and their use as pharmaceutical compositions |
US20060142310A1 (en) * | 2004-11-05 | 2006-06-29 | Boehringer Ingelheim International Gmbh | Process for the preparation of chiral 8-(-3-aminopiperidin-1-yl) xanthines |
US20080249089A1 (en) * | 2002-08-21 | 2008-10-09 | Boehringer Ingelheim Pharma Kg | 8-[3-amino-piperidin-1-yl]-xanthines, the preparation thereof and their use as pharmaceutical compositions |
US20080312243A1 (en) * | 2004-06-24 | 2008-12-18 | Matthias Eckhardt | Imidazoles and triazoles, their preparation, and their use as pharmaceutical compositions |
WO2009021740A2 (de) | 2007-08-15 | 2009-02-19 | Sanofis-Aventis | Substituierte tetrahydronaphthaline, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
US7495002B2 (en) | 2004-09-14 | 2009-02-24 | Boehringer Ingelheim International Gmbh | 3-methyl-7-butinyl-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 |
US20090088569A1 (en) * | 2004-04-10 | 2009-04-02 | Matthias Eckhardt | 2-amino-imidazo[4,5-d]pyridazin-4-ones, their preparation, and their use as pharmaceutical compositions |
US20090137801A1 (en) * | 2004-02-18 | 2009-05-28 | Boehringer Ingelheim International Gmbh | 8-[3-amino-piperidin-1-yl]-xanthines, their preparation and their use as pharmaceutical compositions |
US7560450B2 (en) | 2002-11-21 | 2009-07-14 | Boehringer Ingelheim Pharma Gmbh & Co., Kg | Xanthine derivatives, the preparation thereof and their use as pharmaceutical compositions |
US7645763B2 (en) | 2004-02-23 | 2010-01-12 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | 8-[3-amino-piperidin-1-yl]-xanthines, their preparation and their use as pharmaceutical composition |
US7667035B2 (en) | 2004-05-10 | 2010-02-23 | Boehringer Ingelheim International Gmbh | Imidazole derivatives, their preparation and their use as intermediates for the preparation of pharmaceutical compositions and pesticides |
US7696212B2 (en) | 2002-11-08 | 2010-04-13 | Boehringer Ingelheim Pharma Gmbh And Co. Kg | Xanthine derivatives, the preparation thereof and their use as pharmaceutical compositions |
WO2010086411A1 (en) * | 2009-01-29 | 2010-08-05 | Boehringer Ingelheim International Gmbh | Dpp-iv inhibitors for treatment of diabetes in paediatric patients |
US20110178134A1 (en) * | 2008-02-07 | 2011-07-21 | Sanofi-Aventis | Novel phenyl-substituted imidazolidines, process for preparation thereof, medicaments comprising said compounds and use thereof |
US20110195917A1 (en) * | 2007-08-16 | 2011-08-11 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition comprising a glucopyranosyl-substituted benzene derivate |
WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
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 |
US8071583B2 (en) | 2006-08-08 | 2011-12-06 | Boehringer Ingelheim International Gmbh | Pyrrolo[3,2-D] pyrimidines as DPP-IV inhibitors for the treatment of diabetes mellitus |
WO2011157827A1 (de) | 2010-06-18 | 2011-12-22 | Sanofi | Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen |
WO2011161030A1 (de) | 2010-06-21 | 2011-12-29 | Sanofi | Heterocyclisch substituierte methoxyphenylderivate mit oxogruppe, verfahren zu ihrer herstellung und ihre verwendung als gpr40 rezeptor modulatoren |
WO2012004269A1 (de) | 2010-07-05 | 2012-01-12 | Sanofi | ( 2 -aryloxy -acetylamino) - phenyl - propionsäurederivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
WO2012004270A1 (de) | 2010-07-05 | 2012-01-12 | Sanofi | Spirocyclisch substituierte 1,3-propandioxidderivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
WO2012010413A1 (de) | 2010-07-05 | 2012-01-26 | Sanofi | Aryloxy-alkylen-substituierte hydroxy-phenyl-hexinsäuren, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
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 |
US8232281B2 (en) | 2006-05-04 | 2012-07-31 | Boehringer Ingelheim International Gmbh | Uses of DPP-IV inhibitors |
WO2012120053A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Verzweigte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
WO2012120052A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Mit carbozyklen oder heterozyklen substituierte oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
WO2012120055A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
WO2012120054A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
WO2012120056A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Tetrasubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
WO2013045413A1 (en) | 2011-09-27 | 2013-04-04 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
US8513264B2 (en) | 2008-09-10 | 2013-08-20 | Boehringer Ingelheim International Gmbh | Combination therapy for the treatment of diabetes and related conditions |
WO2014064215A1 (en) | 2012-10-24 | 2014-05-01 | INSERM (Institut National de la Santé et de la Recherche Médicale) | TPL2 KINASE INHIBITORS FOR PREVENTING OR TREATING DIABETES AND FOR PROMOTING β-CELL SURVIVAL |
US8846695B2 (en) | 2009-01-07 | 2014-09-30 | Boehringer Ingelheim International Gmbh | Treatment for diabetes in patients with inadequate glycemic control despite metformin therapy comprising a DPP-IV inhibitor |
US8853156B2 (en) | 2008-08-06 | 2014-10-07 | Boehringer Ingelheim International Gmbh | Treatment for diabetes in patients inappropriate for metformin therapy |
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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 US US15/285,871 patent/US9815837B2/en active Active
- 2016-10-05 JP JP2016197147A patent/JP6309589B2/ja active Active
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2017
- 2017-10-05 US US15/725,426 patent/US10301313B2/en active Active
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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
- 2021-06-30 US US17/363,441 patent/US11919903B2/en active Active
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