CA2802541A1 - Compositions of 5-ethyl-2-{4-[4-(4-tetrazol-1-yl-phenoxymethyl)-thiazol-2-yl]-piperidin-1-yl}-pyrimidine - Google Patents
Compositions of 5-ethyl-2-{4-[4-(4-tetrazol-1-yl-phenoxymethyl)-thiazol-2-yl]-piperidin-1-yl}-pyrimidine Download PDFInfo
- Publication number
- CA2802541A1 CA2802541A1 CA2802541A CA2802541A CA2802541A1 CA 2802541 A1 CA2802541 A1 CA 2802541A1 CA 2802541 A CA2802541 A CA 2802541A CA 2802541 A CA2802541 A CA 2802541A CA 2802541 A1 CA2802541 A1 CA 2802541A1
- Authority
- CA
- Canada
- Prior art keywords
- ethyl
- compound
- pyrimidine
- tetrazol
- thiazol
- 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
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 78
- NFTMKHWBOINJGM-UHFFFAOYSA-N 2-[1-(5-ethylpyrimidin-2-yl)piperidin-4-yl]-4-[[4-(tetrazol-1-yl)phenoxy]methyl]-1,3-thiazole Chemical group N1=CC(CC)=CN=C1N1CCC(C=2SC=C(COC=3C=CC(=CC=3)N3N=NN=C3)N=2)CC1 NFTMKHWBOINJGM-UHFFFAOYSA-N 0.000 title claims description 73
- 238000000034 method Methods 0.000 claims abstract description 105
- -1 4- tetrazol - 1 -yl -phenoxymethyl Chemical group 0.000 claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims description 97
- 239000007962 solid dispersion Substances 0.000 claims description 56
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 53
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- 238000010922 spray-dried dispersion Methods 0.000 claims description 51
- 229920000642 polymer Polymers 0.000 claims description 45
- 229920000623 Cellulose acetate phthalate Polymers 0.000 claims description 42
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 42
- 229940081734 cellulose acetate phthalate Drugs 0.000 claims description 42
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- 239000008103 glucose Substances 0.000 claims description 34
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 33
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- ZUAAPNNKRHMPKG-UHFFFAOYSA-N acetic acid;butanedioic acid;methanol;propane-1,2-diol Chemical compound OC.CC(O)=O.CC(O)CO.OC(=O)CCC(O)=O ZUAAPNNKRHMPKG-UHFFFAOYSA-N 0.000 claims description 5
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
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- 229940090181 propyl acetate Drugs 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 2
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- JKQCZAKAXNWFFN-UHFFFAOYSA-N butan-2-one;4-methylpentan-2-one Chemical compound CCC(C)=O.CC(C)CC(C)=O JKQCZAKAXNWFFN-UHFFFAOYSA-N 0.000 claims 1
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- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 18
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- 238000012216 screening Methods 0.000 description 18
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 16
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- 238000006243 chemical reaction Methods 0.000 description 15
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- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 14
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
- A61K9/1652—Polysaccharides, e.g. alginate, cellulose derivatives; Cyclodextrin
-
- 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
- A61K31/397—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having four-membered rings, e.g. azetidine
-
- 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
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| WO2010048149A2 (en) | 2008-10-20 | 2010-04-29 | Kalypsys, Inc. | Heterocyclic modulators of gpr119 for treatment of disease |
| US20110160222A1 (en) | 2008-11-26 | 2011-06-30 | Metabolex, Inc. | Modulators of glucose homeostasis for the treatment of diabetes and metabolic disorders |
| JP5667180B2 (ja) | 2009-07-01 | 2015-02-12 | イオン メディックス インコーポレイテッド | 哺乳類の有核細胞に由来するマイクロベシクル及びその用途 |
| WO2011041154A1 (en) * | 2009-10-01 | 2011-04-07 | Metabolex, Inc. | Substituted tetrazol-1-yl-phenoxymethyl-thiazol-2-yl-piperidinyl-pyrimidine salts |
| WO2011153435A1 (en) | 2010-06-04 | 2011-12-08 | Metabolex, Inc. | Preparation of 5-ethyl-2-{4-[4-(4-tetrazol-1-yl-phenoxymethyl)-thiazol-2-yl]-piperidin-1-yl}-pyrimidine |
| EP2585048B1 (en) | 2010-06-23 | 2018-04-11 | CymaBay Therapeutics, Inc. | Compositions of 5-ethyl-2-{4-[4-(4-tetrazol-1-yl-phenoxymethyl)-thiazol-2-yl]-piperidin-1-yl}-pyrimidine |
| US20120184572A1 (en) | 2011-01-13 | 2012-07-19 | Metabolex, Inc. | Aryl gpr119 agonists and uses thereof |
-
2011
- 2011-06-17 EP EP11728490.1A patent/EP2585048B1/en not_active Not-in-force
- 2011-06-17 BR BR112012032248A patent/BR112012032248A2/pt not_active Application Discontinuation
- 2011-06-17 WO PCT/US2011/040972 patent/WO2011163090A1/en not_active Ceased
- 2011-06-17 CN CN2011800283946A patent/CN103037843A/zh active Pending
- 2011-06-17 CA CA2802541A patent/CA2802541A1/en not_active Abandoned
- 2011-06-17 JP JP2013516636A patent/JP5847813B2/ja not_active Expired - Fee Related
- 2011-06-17 CN CN201910082228.2A patent/CN109674753A/zh active Pending
- 2011-06-17 ES ES11728490.1T patent/ES2676209T3/es active Active
- 2011-06-21 US US13/165,651 patent/US9241924B2/en active Active
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2016
- 2016-01-21 US US15/002,498 patent/US10098843B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN109674753A (zh) | 2019-04-26 |
| WO2011163090A1 (en) | 2011-12-29 |
| EP2585048A1 (en) | 2013-05-01 |
| JP2013529637A (ja) | 2013-07-22 |
| BR112012032248A2 (pt) | 2016-09-13 |
| US20160213618A1 (en) | 2016-07-28 |
| JP5847813B2 (ja) | 2016-01-27 |
| EP2585048B1 (en) | 2018-04-11 |
| US9241924B2 (en) | 2016-01-26 |
| ES2676209T3 (es) | 2018-07-17 |
| CN103037843A (zh) | 2013-04-10 |
| US10098843B2 (en) | 2018-10-16 |
| US20110318418A1 (en) | 2011-12-29 |
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