ES2429525T3 - Sal de citrato de 9E-15-(2-pirrolidin-1-il-etoxi)-7,12,25-trioxa-19,21,24-triaza-tetraciclo[18.3.1.1(2,5).1(14)18)]-hexacosa-1(24),2,4,9,14,16,18(26),20,22-nonaeno - Google Patents
Sal de citrato de 9E-15-(2-pirrolidin-1-il-etoxi)-7,12,25-trioxa-19,21,24-triaza-tetraciclo[18.3.1.1(2,5).1(14)18)]-hexacosa-1(24),2,4,9,14,16,18(26),20,22-nonaeno Download PDFInfo
- Publication number
- ES2429525T3 ES2429525T3 ES10737645T ES10737645T ES2429525T3 ES 2429525 T3 ES2429525 T3 ES 2429525T3 ES 10737645 T ES10737645 T ES 10737645T ES 10737645 T ES10737645 T ES 10737645T ES 2429525 T3 ES2429525 T3 ES 2429525T3
- Authority
- ES
- Spain
- Prior art keywords
- salt
- ray diffraction
- shows
- salt according
- citrate
- 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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Links
- 150000001860 citric acid derivatives Chemical class 0.000 title claims abstract description 37
- -1 2-pyrrolidin-1-yl-ethoxy Chemical group 0.000 title claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims description 29
- 238000002441 X-ray diffraction Methods 0.000 claims description 24
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 230000002062 proliferating effect Effects 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 206010028980 Neoplasm Diseases 0.000 claims description 5
- 201000011510 cancer Diseases 0.000 claims description 5
- 239000000523 sample Substances 0.000 description 30
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 29
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Natural products OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 28
- 238000000634 powder X-ray diffraction Methods 0.000 description 27
- 239000002904 solvent Substances 0.000 description 26
- 238000010586 diagram Methods 0.000 description 23
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- 238000010992 reflux Methods 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 14
- 239000012458 free base Substances 0.000 description 13
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 12
- 238000001179 sorption measurement Methods 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 11
- 229940125904 compound 1 Drugs 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- 239000013543 active substance Substances 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- 238000000113 differential scanning calorimetry Methods 0.000 description 9
- 238000004090 dissolution Methods 0.000 description 9
- 238000002017 high-resolution X-ray diffraction Methods 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- 238000002425 crystallisation Methods 0.000 description 7
- 230000008025 crystallization Effects 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 101100452593 Caenorhabditis elegans ina-1 gene Proteins 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 4
- WWCDLXGTIXEJRY-UHFFFAOYSA-N 2-hydroxypropane-1,2,3-tricarboxylic acid;propan-2-one Chemical compound CC(C)=O.OC(=O)CC(O)(C(O)=O)CC(O)=O WWCDLXGTIXEJRY-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000013480 data collection Methods 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 230000036571 hydration Effects 0.000 description 3
- 238000006703 hydration reaction Methods 0.000 description 3
- 230000010354 integration Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 101100154785 Mus musculus Tulp2 gene Proteins 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 230000009897 systematic effect Effects 0.000 description 2
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 1
- 241000005672 Baia Species 0.000 description 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000010954 commercial manufacturing process Methods 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000007416 differential thermogravimetric analysis Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 108091029067 miR-11 stem-loop Proteins 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical class C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 238000011170 pharmaceutical development Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/18—Bridged systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22560909P | 2009-07-15 | 2009-07-15 | |
| US225609P | 2009-07-15 | ||
| PCT/SG2010/000265 WO2011008172A1 (en) | 2009-07-15 | 2010-07-14 | 9e-15-(2-pyrrolidin-1-yl-ethoxy)-7,12,25-trioxa-19,21,24-triaza- tetracyclo[18.3.1.1(2,5).1(14)18)]hexacosa-1(24),2,4,9,14,16,18(26),20,22-nonaene citrate salt |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2429525T3 true ES2429525T3 (es) | 2013-11-15 |
Family
ID=42790728
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES10737645T Active ES2429525T3 (es) | 2009-07-15 | 2010-07-14 | Sal de citrato de 9E-15-(2-pirrolidin-1-il-etoxi)-7,12,25-trioxa-19,21,24-triaza-tetraciclo[18.3.1.1(2,5).1(14)18)]-hexacosa-1(24),2,4,9,14,16,18(26),20,22-nonaeno |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US9062074B2 (https=) |
| EP (1) | EP2454266B1 (https=) |
| JP (2) | JP6013911B2 (https=) |
| CN (1) | CN102762577B (https=) |
| AR (2) | AR077483A1 (https=) |
| BR (1) | BR112012000750B1 (https=) |
| CA (1) | CA2768210C (https=) |
| DK (1) | DK2454266T3 (https=) |
| ES (1) | ES2429525T3 (https=) |
| HR (1) | HRP20130941T1 (https=) |
| MX (1) | MX2012000680A (https=) |
| PL (1) | PL2454266T3 (https=) |
| PT (1) | PT2454266E (https=) |
| RU (1) | RU2543721C2 (https=) |
| SI (1) | SI2454266T1 (https=) |
| SM (1) | SMT201300112B (https=) |
| TW (1) | TWI537276B (https=) |
| WO (1) | WO2011008172A1 (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113559075A (zh) | 2014-11-17 | 2021-10-29 | 康泰科思特生物制药公司 | 奥那司酮延长释放组合物和方法 |
| AU2016326657B2 (en) | 2015-09-25 | 2019-10-24 | Context Biopharma, Inc. | Methods of making onapristone intermediates |
| EP3389632A4 (en) | 2015-12-15 | 2019-11-06 | Context Biopharma Inc. | AMORPHIC ONAPRISTON COMPOSITIONS AND METHOD FOR THE PRODUCTION THEREOF |
| WO2018102369A1 (en) | 2016-11-30 | 2018-06-07 | Arno Therapeutics, Inc. | Methods for onapristone synthesis dehydration and deprotection |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY110603A (en) * | 1993-05-27 | 1998-08-29 | Novartis Ag | Tetrahydropyran derivatives |
| WO2004078682A2 (en) * | 2003-03-05 | 2004-09-16 | Irm Llc | Cyclic compounds and compositions as protein kinase inhibitors |
| NZ568325A (en) | 2005-11-16 | 2011-05-27 | S Bio Pte Ltd | Macrocyclic oxygen linked pyrimidine derivatives |
-
2010
- 2010-07-14 PL PL10737645T patent/PL2454266T3/pl unknown
- 2010-07-14 CN CN201080032627.5A patent/CN102762577B/zh active Active
- 2010-07-14 JP JP2012520571A patent/JP6013911B2/ja active Active
- 2010-07-14 US US13/384,139 patent/US9062074B2/en active Active
- 2010-07-14 DK DK10737645.1T patent/DK2454266T3/da active
- 2010-07-14 PT PT107376451T patent/PT2454266E/pt unknown
- 2010-07-14 RU RU2012105044/04A patent/RU2543721C2/ru active
- 2010-07-14 BR BR112012000750-5A patent/BR112012000750B1/pt active IP Right Grant
- 2010-07-14 SI SI201030347T patent/SI2454266T1/sl unknown
- 2010-07-14 WO PCT/SG2010/000265 patent/WO2011008172A1/en not_active Ceased
- 2010-07-14 HR HRP20130941AT patent/HRP20130941T1/hr unknown
- 2010-07-14 EP EP10737645.1A patent/EP2454266B1/en active Active
- 2010-07-14 ES ES10737645T patent/ES2429525T3/es active Active
- 2010-07-14 MX MX2012000680A patent/MX2012000680A/es active IP Right Grant
- 2010-07-14 CA CA2768210A patent/CA2768210C/en active Active
- 2010-07-15 TW TW099123331A patent/TWI537276B/zh active
- 2010-07-15 AR ARP100102594A patent/AR077483A1/es not_active Application Discontinuation
-
2013
- 2013-10-04 SM SM201300112T patent/SMT201300112B/xx unknown
-
2015
- 2015-05-07 JP JP2015094972A patent/JP2015164941A/ja active Pending
-
2019
- 2019-08-05 AR ARP190102219A patent/AR114987A2/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2768210A1 (en) | 2011-01-20 |
| DK2454266T3 (da) | 2013-09-08 |
| CA2768210C (en) | 2017-08-15 |
| EP2454266A1 (en) | 2012-05-23 |
| CN102762577A (zh) | 2012-10-31 |
| AR114987A2 (es) | 2020-11-11 |
| RU2012105044A (ru) | 2013-08-20 |
| BR112012000750B1 (pt) | 2021-05-25 |
| JP2015164941A (ja) | 2015-09-17 |
| TWI537276B (zh) | 2016-06-11 |
| JP2012533539A (ja) | 2012-12-27 |
| AR077483A1 (es) | 2011-08-31 |
| SMT201300112B (it) | 2013-11-08 |
| RU2543721C2 (ru) | 2015-03-10 |
| SI2454266T1 (sl) | 2013-10-30 |
| BR112012000750A2 (pt) | 2016-08-09 |
| BR112012000750A8 (pt) | 2018-02-06 |
| US20120196876A1 (en) | 2012-08-02 |
| HRP20130941T1 (hr) | 2013-11-08 |
| CN102762577B (zh) | 2015-01-07 |
| JP6013911B2 (ja) | 2016-10-25 |
| WO2011008172A1 (en) | 2011-01-20 |
| EP2454266B1 (en) | 2013-07-10 |
| US9062074B2 (en) | 2015-06-23 |
| MX2012000680A (es) | 2012-02-28 |
| HK1178159A1 (en) | 2013-09-06 |
| PT2454266E (pt) | 2013-10-10 |
| TW201107336A (en) | 2011-03-01 |
| PL2454266T3 (pl) | 2014-01-31 |
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