ES2527354T3 - Anhidrato de 8-cloro-3-pentil-3,7-dihidro-1H-purina-2,6-diona 2-amino-2-(hidroximetil)-1,3-propanodiol para el tratamiento de enfermedades - Google Patents
Anhidrato de 8-cloro-3-pentil-3,7-dihidro-1H-purina-2,6-diona 2-amino-2-(hidroximetil)-1,3-propanodiol para el tratamiento de enfermedades Download PDFInfo
- Publication number
- ES2527354T3 ES2527354T3 ES09832421.3T ES09832421T ES2527354T3 ES 2527354 T3 ES2527354 T3 ES 2527354T3 ES 09832421 T ES09832421 T ES 09832421T ES 2527354 T3 ES2527354 T3 ES 2527354T3
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- Prior art keywords
- anhydrate
- dihydro
- pentyl
- chloro
- purine
- 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.)
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- HNAXNEBDLULUPW-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;8-chloro-3-pentyl-7h-purine-2,6-dione Chemical compound OCC(N)(CO)CO.O=C1NC(=O)N(CCCCC)C2=C1NC(Cl)=N2 HNAXNEBDLULUPW-UHFFFAOYSA-N 0.000 title claims abstract 3
- 201000010099 disease Diseases 0.000 title 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 229960000913 crospovidone Drugs 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229920000523 polyvinylpolypyrrolidone Polymers 0.000 description 4
- 235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 4
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 4
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 4
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 4
- CGAMDQCXAAOFSR-UHFFFAOYSA-N 8-chloro-3-pentyl-7h-purine-2,6-dione Chemical compound O=C1NC(=O)N(CCCCC)C2=C1NC(Cl)=N2 CGAMDQCXAAOFSR-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 229940069328 povidone Drugs 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- 229930195725 Mannitol Natural products 0.000 description 2
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 2
- -1 Tris Hydroxyl Methyl Aminomethane salt Chemical class 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000007888 film coating Substances 0.000 description 2
- 238000009501 film coating Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000594 mannitol Substances 0.000 description 2
- 235000010355 mannitol Nutrition 0.000 description 2
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 2
- 239000008108 microcrystalline cellulose Substances 0.000 description 2
- 229940016286 microcrystalline cellulose Drugs 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000009331 sowing Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 230000002238 attenuated effect Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229940057948 magnesium stearate Drugs 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 238000013094 purity test Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/133—Amines having hydroxy groups, e.g. sphingosine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- 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
- A61P3/06—Antihyperlipidemics
-
- 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
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
-
- 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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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
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- Diabetes (AREA)
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- Cardiology (AREA)
- Epidemiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Obesity (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Nutrition Science (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
Un compuesto que es anhidrato de tris(hidroximetil)aminometano de 8-cloro-3-pentil-3,7-dihidro-1H-purina-2,6- diona (Fórmula (IA):**Fórmula**
Description
E09832421
05-01-2015
- 17,5
- 5,1
- 17,9
- 5,0
- 18,3
- 4,8
- 19,2
- 4,6
- 19,8
- 4,5
- 20,2
- 4,4
- 20,6
- 4,3
- 20,9
- 4,2
- 21,7
- 4,1
- 22,1
- 4,0
- 23,3
- 3,8
- 23,9
- 3,7
- 24,6
- 3,6
- 26,3
- 3,4
- 27,1
- 3,3
- 27,9
- 3,2
- 28,2
- 3,2
- 28,6
- 3,1
- 29,6
- 3,0
En otro aspecto, el compuesto de Fórmula (IA) como anhidrato en forma cristalina se caracteriza por un patrón de XRPD que es sustancialmente como se muestra en la Figura 2.
En un aspecto, el compuesto de Fórmula (IA) como anhidrato en forma cristalina se caracteriza por una endoterma
5 de fusión con una temperatura de activación de fusión de 212 ± 2 °C determinado por Calorimetría de Exploración Diferencial (DSC). Convenientemente, mediante el uso de un crisol de aluminio, ligeramente ondulado sin sellado y usando una velocidad de calentamiento de 10°C min-1 .
En un aspecto, el compuesto de Fórmula (IA) como anhidrato en forma cristalina se caracteriza por los siguientes picos de absorción en un espectro de infrarrojo de reflexión total atenuada (ATR-IR) del producto sólido: 3370, 3041,
En otro aspecto, el compuesto de Fórmula (IA) como anhidrato en forma cristalina se caracteriza por tener un espectro de ATR-IR que es sustancialmente como se muestra en la Figura 6.
Como se discute e ilustra a través de todo el documento, la presente invención incluye ciertas formas cristalinas del estado sólido. Existen numerosos métodos para caracterizar dichas formas, y la invención no debe limitarse por los
15 métodos elegidos o la instrumentación usada para caracterizar los compuestos de la presente invención. Por ejemplo, con relación a los patrones de difracción de rayos X, pueden variar las intensidades del pico de difracción en los patrones experimentales, como es sabido en la técnica, principalmente debido a la orientación preferida (no aleatoria) de los cristales) en la muestra preparada. Como tal, el alcance de la presente invención debe considerarse a la luz de la variabilidad de la caracterización que es apreciada por los expertos en la técnica.
20 En un aspecto, la presente invención se refiere a composiciones farmacéuticas que comprenden el compuesto de Fórmula (IA) como anhidrato en forma cristalina.
En un aspecto, la presente invención se refiere al uso del compuesto de Fórmula (IA) como anhidrato en forma cristalina en terapia.
En otro aspecto, la presente invención se refiere al compuesto de Fórmula (IA) como anhidrato en forma cristalina
4
E09832421
05-01-2015
Ejemplo 3
Preparación de sal de Tris Hidroxil Metil Aminometano de 8-Cloro-3-Pentil-3,7-Dihidro-1H-Purina-2,6-Diona
8-Cloro-3-pentil-3,7-dihidro-1H-purina-2,6-diona (29kg) fue disuelta en DMSO (40L) a una temperatura elevada de aprox. 90 a 100 0C y se filtró a través de un filtro de 5 micrómetros, seguido por un lavado en línea de DMSO (13L). 5 Se disolvió tris(hidroximetil)aminometano (15,1 kg) en agua (44L) y se filtró a través de un filtro de 5 micrómetros dentro del mismo recipiente que el ácido madre, seguido por un lavado en línea de agua (15L). El contenido del recipiente fue luego calentado hasta aproximadamente 95 0C para asegurar que se obtenía una solución transparente. El contenido fue enfriado a 88 0C y sembrado con cristales de siembra, en donde los cristales de siembra, formados de la misma manera a partir de una cristalización de acetona en agua u, obtenidos tal cual, o de
10 un procedimiento del Ejemplo 1 anterior. En este procedimiento, la cristalización es sembrada para proporcionar el control del tamaño de partícula y asegurar que la forma del producto deseado fuera obtenida. El lodo sembrado fue mantenido por aproximadamente 30 minutos y enfriado a 0 0C. El producto fue aislado por filtración, lavado con ~5 0C DMSO/agua (1:1, 58L) y ~5°C acetona (2 x 58L). El producto resultante fue secado a 50 0C bajo vacío. Rendimiento: 35,4 kg (83% de rendimiento).
15 Ejemplo 4
Preparación de una formulación de sal de Tris Hidroxil Metil Aminometano de 8-Cloro-3-Pentil-3,7-Dihidro-1H-Purina2,6-Diona
- Componente
- Cantidad (mg/tableta)
- 25 mg
- 50 mg 100 mg
- Granulación Sal de tris1 Polvo de manitol Povidona Crospovidona Agua purificada2
- 36,75 9,25 2,50 1,50 c.s. 73,50 18,50 5,00 3,00 c.s. 147,00 37,00 10,00 6,00 c.s.
- Combinación de compresión Celulosa microcristalina Crospovidona Estearato de Magnesio3
- 338,00 8,00 4,00 280,00 16,00 4,00 172,00 24,00 4,00
- Revestimiento de película acuosa Opadry White OY-S-9603 Agua purificada2
- 12,00 c.s. 12,00 c.s. 12,00 c.s.
- Peso de la tableta
- 412,00 412,00 412,00
1 Una cantidad de 36,75mg, 73,50 mg o 147,00 mg de sal de Tris es requerida para lograr 25mg, 50mg o 100mg del
20 ácido libre respectivamente, calculado por un factor de conversión de 1,47. La cantidad de sustancia de un fármaco puede ajustarse con base en el ensayo de pureza.
2 Se separó agua durante el procesamiento.
3 Fuente Vegetal.
La sal de tris, polvo de manitol, povidona, crospovidona y agua purificada fueron granulados utilizando un granulador
25 del lecho fluido. El lecho fluido fue luego secado. El granulado fue combinado con celulosa microcristalina, crospovidona y estearato de magnesio y comprimido en una prensa de tabletas. Las tabletas resultantes fueron luego cubiertas con un revestimiento de película acuoso de opadry y agua.
La povidona (polivinilpirrolidona) es un polímero sintético que consiste en grupos lineales de 1-vinil-2-pirrolidona y
11
Claims (2)
- REIVINDICACIONES
- 1.
- Un compuesto que es anhidrato de tris(hidroximetil)aminometano de 8-cloro-3-pentil-3,7-dihidro-1H-purina-2,6diona (Fórmula (IA):
-
- 2.
- Un compuesto según la reivindicación 1, en donde la forma cristalina del compuesto está caracterizada por un patrón de XRPD que comprende los siguientes picos:
imagen1 - Posición (±0,2°2-theta)
- Distancia interplanar d ((Å))
- 10,1
- 8,7
- 10,5
- 8,4
- 12,2
- 7,3
- 13,0
- 6,8
- 13,5
- 6,5
- 17,3
- 5,1
- 17,5
- 5,1
- 17,9
- 5,0
- 18,3
- 4,8
- 19,2
- 4,6
- 19,8
- 4,5
- 20,2
- 4,4
- 20,6
- 4,3
- 20,9
- 4,2
- 21,7
- 4,1
- 22,1
- 4,0
- 23,3
- 3,8
- 23,9
- 3,7
- 24,6
- 3,6
- 26,3
- 3,4
- 27,1
- 3,3
- 27,9
- 3,2
15imagen2
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12059608P | 2008-12-08 | 2008-12-08 | |
| US120596P | 2008-12-08 | ||
| PCT/US2009/066941 WO2010068581A1 (en) | 2008-12-08 | 2009-12-07 | Novel compounds |
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| Publication Number | Publication Date |
|---|---|
| ES2527354T3 true ES2527354T3 (es) | 2015-01-22 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES09832421.3T Active ES2527354T3 (es) | 2008-12-08 | 2009-12-07 | Anhidrato de 8-cloro-3-pentil-3,7-dihidro-1H-purina-2,6-diona 2-amino-2-(hidroximetil)-1,3-propanodiol para el tratamiento de enfermedades |
Country Status (22)
| Country | Link |
|---|---|
| US (3) | US9163024B2 (es) |
| EP (1) | EP2370440B1 (es) |
| JP (1) | JP5666464B2 (es) |
| KR (1) | KR101743783B1 (es) |
| CN (1) | CN102245606B (es) |
| AU (1) | AU2009324811B2 (es) |
| BR (1) | BRPI0922134A2 (es) |
| CA (1) | CA2746316C (es) |
| CY (1) | CY1116032T1 (es) |
| DK (1) | DK2370440T3 (es) |
| EA (1) | EA020037B1 (es) |
| ES (1) | ES2527354T3 (es) |
| HR (1) | HRP20150026T1 (es) |
| IL (1) | IL213032A (es) |
| MX (1) | MX2011006022A (es) |
| PL (1) | PL2370440T3 (es) |
| PT (1) | PT2370440E (es) |
| RS (1) | RS53777B1 (es) |
| SI (1) | SI2370440T1 (es) |
| SM (1) | SMT201500012B (es) |
| WO (1) | WO2010068581A1 (es) |
| ZA (1) | ZA201103397B (es) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101103030B (zh) * | 2004-02-14 | 2010-10-13 | 史密丝克莱恩比彻姆公司 | 具有hm74a受体活性的药物 |
| JP2009504592A (ja) | 2005-08-10 | 2009-02-05 | スミスクライン・ビーチャム・コーポレイション | 選択的ｈｍ７４ａアゴニストとしてのキサンチン誘導体 |
| ES2674951T3 (es) * | 2012-03-22 | 2018-07-05 | Transtech Pharma, Llc | Sales de tris(hidroximetil)aminometano de un agonista de GLP1R de molécula pequeña y composiciones farmacéuticas y usos de las mismas |
| AU2024229006A1 (en) * | 2023-02-27 | 2025-09-18 | Shanton Pharma Pte. Ltd. | Crystal form of 8-chloro-3-pentyl-3,7-dihydro-1h-purin-2,6-dione compound and preparation method therefor |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3657327A (en) * | 1970-06-01 | 1972-04-18 | Upjohn Co | Prostaglandin salts of tris(hydroxymethyl)aminomethane |
| US4647585A (en) * | 1984-11-08 | 1987-03-03 | E. R. Squibb & Sons, Inc. | Bicycloheptane substituted ethers |
| WO2001043692A2 (en) * | 1999-12-15 | 2001-06-21 | Smithkline Beecham Corporation | SALTS OF Cis-4-CYANO-4-[3-(CYCLOPENTYLOXY)-4-METHOXYPHENYL]CYCLOHEXANE-1-CARBOXYLIC ACID |
| US20030013905A1 (en) | 2002-06-10 | 2003-01-16 | Huang Guishu Kris | Salts of cis-4-cyano-4[3(cyclopentyloxy)-4-methoxyphenyl]cyclohexane-1-carboxylic acid |
| CN101103030B (zh) * | 2004-02-14 | 2010-10-13 | 史密丝克莱恩比彻姆公司 | 具有hm74a受体活性的药物 |
| GB0423568D0 (en) * | 2004-10-22 | 2004-11-24 | Smithkline Beecham Corp | Novel compounds |
| US20090209561A1 (en) | 2004-10-22 | 2009-08-20 | Richard Jonathan Daniel Hatley | Xanthine Derivatives with HM74A Receptor Activity |
| JP2009504592A (ja) | 2005-08-10 | 2009-02-05 | スミスクライン・ビーチャム・コーポレイション | 選択的ｈｍ７４ａアゴニストとしてのキサンチン誘導体 |
| GB0516464D0 (en) * | 2005-08-10 | 2005-09-14 | Smithkline Beecham Corp | Novel compounds |
-
2009
- 2009-12-07 AU AU2009324811A patent/AU2009324811B2/en not_active Ceased
- 2009-12-07 BR BRPI0922134-4A patent/BRPI0922134A2/pt not_active Application Discontinuation
- 2009-12-07 US US13/133,486 patent/US9163024B2/en not_active Expired - Fee Related
- 2009-12-07 EA EA201170783A patent/EA020037B1/ru not_active IP Right Cessation
- 2009-12-07 PT PT98324213T patent/PT2370440E/pt unknown
- 2009-12-07 CA CA2746316A patent/CA2746316C/en not_active Expired - Fee Related
- 2009-12-07 KR KR1020117012975A patent/KR101743783B1/ko not_active Expired - Fee Related
- 2009-12-07 SI SI200931113T patent/SI2370440T1/sl unknown
- 2009-12-07 WO PCT/US2009/066941 patent/WO2010068581A1/en not_active Ceased
- 2009-12-07 RS RS20150086A patent/RS53777B1/sr unknown
- 2009-12-07 CN CN200980148973.7A patent/CN102245606B/zh not_active Expired - Fee Related
- 2009-12-07 MX MX2011006022A patent/MX2011006022A/es active IP Right Grant
- 2009-12-07 PL PL09832421T patent/PL2370440T3/pl unknown
- 2009-12-07 DK DK09832421.3T patent/DK2370440T3/en active
- 2009-12-07 JP JP2011539772A patent/JP5666464B2/ja not_active Expired - Fee Related
- 2009-12-07 ES ES09832421.3T patent/ES2527354T3/es active Active
- 2009-12-07 HR HRP20150026AT patent/HRP20150026T1/hr unknown
- 2009-12-07 EP EP09832421.3A patent/EP2370440B1/en active Active
-
2011
- 2011-05-10 ZA ZA2011/03397A patent/ZA201103397B/en unknown
- 2011-05-19 IL IL213032A patent/IL213032A/en not_active IP Right Cessation
-
2014
- 2014-12-16 CY CY20141101047T patent/CY1116032T1/el unknown
-
2015
- 2015-01-16 SM SM201500012T patent/SMT201500012B/xx unknown
- 2015-08-31 US US14/840,549 patent/US20150366870A1/en not_active Abandoned
-
2016
- 2016-10-11 US US15/289,996 patent/US20170027945A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| PL2370440T3 (pl) | 2015-05-29 |
| ZA201103397B (en) | 2012-01-25 |
| CA2746316A1 (en) | 2010-06-17 |
| KR101743783B1 (ko) | 2017-06-05 |
| IL213032A (en) | 2015-02-26 |
| KR20110097816A (ko) | 2011-08-31 |
| DK2370440T3 (en) | 2014-12-08 |
| US20110251218A1 (en) | 2011-10-13 |
| US20170027945A1 (en) | 2017-02-02 |
| WO2010068581A1 (en) | 2010-06-17 |
| RS53777B1 (sr) | 2015-06-30 |
| CN102245606A (zh) | 2011-11-16 |
| EP2370440B1 (en) | 2014-11-12 |
| EP2370440A4 (en) | 2012-05-30 |
| SI2370440T1 (sl) | 2015-02-27 |
| AU2009324811A1 (en) | 2011-06-23 |
| US9163024B2 (en) | 2015-10-20 |
| MX2011006022A (es) | 2011-06-28 |
| JP2012511028A (ja) | 2012-05-17 |
| US20150366870A1 (en) | 2015-12-24 |
| CN102245606B (zh) | 2014-08-20 |
| EA020037B1 (ru) | 2014-08-29 |
| BRPI0922134A2 (pt) | 2015-08-18 |
| EP2370440A1 (en) | 2011-10-05 |
| PT2370440E (pt) | 2015-01-14 |
| IL213032A0 (en) | 2011-07-31 |
| AU2009324811B2 (en) | 2013-01-24 |
| EA201170783A1 (ru) | 2011-12-30 |
| SMT201500012B (it) | 2015-05-03 |
| HRP20150026T1 (hr) | 2015-02-13 |
| CA2746316C (en) | 2017-01-03 |
| CY1116032T1 (el) | 2017-01-25 |
| JP5666464B2 (ja) | 2015-02-12 |
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