WO2008075073A1 - Novel crystalline compound useful as glk activator - Google Patents
Novel crystalline compound useful as glk activator Download PDFInfo
- Publication number
- WO2008075073A1 WO2008075073A1 PCT/GB2007/004925 GB2007004925W WO2008075073A1 WO 2008075073 A1 WO2008075073 A1 WO 2008075073A1 GB 2007004925 W GB2007004925 W GB 2007004925W WO 2008075073 A1 WO2008075073 A1 WO 2008075073A1
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- WIPO (PCT)
- Prior art keywords
- crystalline form
- ray powder
- diffraction pattern
- powder diffraction
- peaks
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- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 229940102213 injectable suspension Drugs 0.000 description 1
- SYJRVVFAAIUVDH-UHFFFAOYSA-N ipa isopropanol Chemical compound CC(C)O.CC(C)O SYJRVVFAAIUVDH-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
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- 230000000670 limiting effect Effects 0.000 description 1
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- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 208000011661 metabolic syndrome X Diseases 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 201000009104 prediabetes syndrome Diseases 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 229910001467 sodium calcium phosphate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000002594 sorbent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- UHSKKTUEMNDYHC-UHFFFAOYSA-N tert-butyl 3-[(3-hydroxy-5-propan-2-yloxybenzoyl)amino]pyrazole-1-carboxylate Chemical compound CC(C)OC1=CC(O)=CC(C(=O)NC2=NN(C=C2)C(=O)OC(C)(C)C)=C1 UHSKKTUEMNDYHC-UHFFFAOYSA-N 0.000 description 1
- XVZDYBIQLDYBEY-UHFFFAOYSA-N tert-butyl 3-[(3-phenylmethoxy-5-propan-2-yloxybenzoyl)amino]pyrazole-1-carboxylate Chemical compound C=1C(C(=O)NC2=NN(C=C2)C(=O)OC(C)(C)C)=CC(OC(C)C)=CC=1OCC1=CC=CC=C1 XVZDYBIQLDYBEY-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- 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
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/12—Antidiuretics, e.g. drugs for diabetes insipidus
Definitions
- the present invention relates to a novel crystalline chemical compound and more particularly to a novel crystalline form of 3- ⁇ [5-(azetidin-l-ylcarbonyl)pyrazin-2-yl]oxy ⁇ -5- [(l-methylethyl)oxy]-N-lH-pyrazol-3-ylbenzamide, hereinafter referred to as "the Agent", and illustrated in Formula (I) hereinafter, which compound is a glucokinase (GLK or GK) activator and useful as a pharmaceutical agent in the treatment or prevention of a disease or medical condition mediated through GLK, leading to a decreased glucose threshold for insulin secretion.
- the invention also relates to processes for the manufacture of the crystalline form, pharmaceutical compositions comprising the crystalline form and the use of the crystalline form in medical treatment.
- the GLK/GLKRP system can be described as a potential "Diabesity" target (of benefit in both Diabetes and Obesity).
- a Form B of the Agent in the preparation of a medicament for use in the combined treatment or prevention, particularly treatment of diabetes and obesity.
- Form B of the Agent in the preparation of a medicament for use in the treatment or prevention, particularly treatment of obesity.
- Form A The X-ray powder diffraction spectra for Form A showed the material to be crystalline. This material had a melting point of 108.5°C (onset).
- Form B 200mg of material was placed in a vial with a magnetic flea, and 2ml of isopropanol (IPA) added. The vial was then sealed tightly with a cap. The slurry was then left to stir on a magnetic plate at ambient temperature (25°C). After 3 days, the sample was removed from the plate, the cap taken off and the slurry left to dry under ambient conditions before it was analysed by XRPD and DSC. This form (Form B) was determined to be crystalline by XRPD and seen to be different to Form A. This material (Form B) had a melting point of 136.8 0 C (onset).
- Analytical Instrument Mettler DSC820e. Typically less than 5mg of material contained in a 40 ⁇ l aluminium pan fitted with a pierced lid was heated over the temperature range 25 0 C to 325 0 C at a constant heating rate of 1O 0 C per minute. A purge gas using nitrogen was used - flow rate 100ml per minute.
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Diabetes (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Hematology (AREA)
- Engineering & Computer Science (AREA)
- Obesity (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Description
Claims
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US12/520,223 US20100094009A1 (en) | 2006-12-21 | 2007-12-20 | Novel crystalline compound useful as glk activator |
CA002671535A CA2671535A1 (en) | 2006-12-21 | 2007-12-20 | Novel crystalline compound useful as glk activator |
BRPI0721143-0A BRPI0721143A2 (en) | 2006-12-21 | 2007-12-20 | CRYSTALINE FORM OF THE COMPOUND PROCESS FOR FORMATION OF THEREOF, USE OF A COMPOUND, METHOD FOR TREATING DISEASES MEDIATED BY GLYCKINASE ACTIVATOR |
MX2009006729A MX2009006729A (en) | 2006-12-21 | 2007-12-20 | Novel crystalline compound useful as glk activator. |
AU2007336016A AU2007336016A1 (en) | 2006-12-21 | 2007-12-20 | Novel crystalline compound useful as GLK activator |
JP2009542221A JP2010513445A (en) | 2006-12-21 | 2007-12-20 | Novel crystalline compounds useful as GLK activators |
EP07848653A EP2121666A1 (en) | 2006-12-21 | 2007-12-20 | Novel crystalline compound useful as glk activator |
NO20092129A NO20092129L (en) | 2006-12-21 | 2009-06-02 | New crystalline compounds useful as GLK activators |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US87125506P | 2006-12-21 | 2006-12-21 | |
US60/871,255 | 2006-12-21 |
Publications (1)
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WO2008075073A1 true WO2008075073A1 (en) | 2008-06-26 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/GB2007/004925 WO2008075073A1 (en) | 2006-12-21 | 2007-12-20 | Novel crystalline compound useful as glk activator |
Country Status (21)
Country | Link |
---|---|
US (2) | US20100094009A1 (en) |
EP (1) | EP2121666A1 (en) |
JP (1) | JP2010513445A (en) |
KR (1) | KR20090090390A (en) |
CN (1) | CN101595104A (en) |
AR (1) | AR064625A1 (en) |
AU (1) | AU2007336016A1 (en) |
BR (1) | BRPI0721143A2 (en) |
CA (1) | CA2671535A1 (en) |
CL (1) | CL2007003805A1 (en) |
CO (1) | CO6190522A2 (en) |
EC (1) | ECSP099427A (en) |
MX (1) | MX2009006729A (en) |
NO (1) | NO20092129L (en) |
PE (1) | PE20081396A1 (en) |
RU (1) | RU2009121756A (en) |
SA (1) | SA07280732B1 (en) |
TW (1) | TW200833339A (en) |
UY (1) | UY30822A1 (en) |
WO (1) | WO2008075073A1 (en) |
ZA (1) | ZA200904296B (en) |
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WO2011107494A1 (en) | 2010-03-03 | 2011-09-09 | Sanofi | Novel aromatic glycoside derivatives, medicaments containing said compounds, and the use thereof |
WO2011157827A1 (en) | 2010-06-18 | 2011-12-22 | Sanofi | Azolopyridin-3-one derivatives as inhibitors of lipases and phospholipases |
WO2011161030A1 (en) | 2010-06-21 | 2011-12-29 | Sanofi | Heterocyclic substituted methoxyphenyl derivatives having an oxo group, method for producing same, and use thereof as gpr40 receptor modulators |
WO2012004269A1 (en) | 2010-07-05 | 2012-01-12 | Sanofi | (2-aryloxy-acetylamino)-phenyl-propionic acid derivatives, method for producing same and use thereof as pharmaceuticals |
WO2012004270A1 (en) | 2010-07-05 | 2012-01-12 | Sanofi | Spirocyclically substituted 1,3-propane dioxide derivatives, methods for the production thereof and use of the same as medicament |
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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 |
US11690841B2 (en) | 2017-09-14 | 2023-07-04 | Queen Mary University Of London | Glycolysis-activating agents for treatment or prevention of disease |
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EP2048137A1 (en) * | 2004-02-18 | 2009-04-15 | AstraZeneca AB | Benzamide derivatives and their use as glucokinase activating agents. |
TW200600086A (en) * | 2004-06-05 | 2006-01-01 | Astrazeneca Ab | Chemical compound |
TW200714597A (en) * | 2005-05-27 | 2007-04-16 | Astrazeneca Ab | Chemical compounds |
EP2305674A1 (en) * | 2005-07-09 | 2011-04-06 | AstraZeneca AB | Heteroaryl benzamide derivatives for use as GLK activators in the treatment of diabetes |
CL2007003061A1 (en) * | 2006-10-26 | 2008-08-01 | Astrazeneca Ab | COMPOUNDS DERIVED FROM 3,5-DIOXI-BENZAMIDA; PREPARATION PROCESS; PHARMACEUTICAL COMPOSITION THAT INCLUDES SUCH COMPOUNDS; AND ITS USE TO TREAT A MEDIUM DISEASE THROUGH GLK, SUCH AS TYPE 2 DIABETES. |
BRPI0917589A2 (en) | 2008-08-04 | 2015-11-17 | Astrazeneca Ab | compound, pharmaceutical composition, use of a compound, method for treating disease, process, pharmaceutical combination, and reaction of methyloxyran-2-carboxylate (ix) with a roh alcohol |
GB0902434D0 (en) * | 2009-02-13 | 2009-04-01 | Astrazeneca Ab | Chemical process |
GB0902406D0 (en) * | 2009-02-13 | 2009-04-01 | Astrazeneca Ab | Crystalline polymorphic form |
AR076221A1 (en) * | 2009-04-09 | 2011-05-26 | Astrazeneca Ab | DERIVED FROM PIRAZOL [4,5-E] PYRIMIDINE AND ITS USE TO TREAT DIABETES AND OBESITY |
AR076220A1 (en) | 2009-04-09 | 2011-05-26 | Astrazeneca Ab | DERIVATIVES OF PIRAZOL [4,5 - E] PYRIMIDINE |
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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 |
US11690841B2 (en) | 2017-09-14 | 2023-07-04 | Queen Mary University Of London | Glycolysis-activating agents for treatment or prevention of disease |
Also Published As
Publication number | Publication date |
---|---|
AU2007336016A1 (en) | 2008-06-26 |
CO6190522A2 (en) | 2010-08-19 |
CN101595104A (en) | 2009-12-02 |
US20100094009A1 (en) | 2010-04-15 |
ECSP099427A (en) | 2009-07-31 |
CL2007003805A1 (en) | 2008-08-01 |
UY30822A1 (en) | 2008-07-31 |
SA07280732B1 (en) | 2011-08-20 |
EP2121666A1 (en) | 2009-11-25 |
AR064625A1 (en) | 2009-04-15 |
BRPI0721143A2 (en) | 2014-03-11 |
RU2009121756A (en) | 2011-01-27 |
KR20090090390A (en) | 2009-08-25 |
ZA200904296B (en) | 2010-04-28 |
US7696191B2 (en) | 2010-04-13 |
JP2010513445A (en) | 2010-04-30 |
TW200833339A (en) | 2008-08-16 |
US20080153800A1 (en) | 2008-06-26 |
PE20081396A1 (en) | 2008-12-05 |
NO20092129L (en) | 2009-06-18 |
MX2009006729A (en) | 2009-08-07 |
CA2671535A1 (en) | 2008-06-26 |
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