BR112012000750B1 - sal citrato cristalino, composição farmacêutica compreendendo o referido sal e uso do mesmo - Google Patents
sal citrato cristalino, composição farmacêutica compreendendo o referido sal e uso do mesmo Download PDFInfo
- Publication number
- BR112012000750B1 BR112012000750B1 BR112012000750-5A BR112012000750A BR112012000750B1 BR 112012000750 B1 BR112012000750 B1 BR 112012000750B1 BR 112012000750 A BR112012000750 A BR 112012000750A BR 112012000750 B1 BR112012000750 B1 BR 112012000750B1
- Authority
- BR
- Brazil
- Prior art keywords
- salt
- shows
- ray diffraction
- fact
- citrate salt
- Prior art date
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- 150000001860 citric acid derivatives Chemical class 0.000 title claims abstract description 43
- 150000003839 salts Chemical class 0.000 title claims abstract description 30
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 7
- 238000002441 X-ray diffraction Methods 0.000 claims description 26
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 230000002062 proliferating effect Effects 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 206010028980 Neoplasm Diseases 0.000 claims description 5
- 201000011510 cancer Diseases 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 230000002265 prevention Effects 0.000 claims 1
- 229940125904 compound 1 Drugs 0.000 abstract description 12
- 238000000034 method Methods 0.000 abstract description 12
- 150000001875 compounds Chemical class 0.000 abstract description 9
- -1 CITRATE SALT Chemical class 0.000 abstract description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Natural products OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 28
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 25
- 239000002904 solvent Substances 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 238000000634 powder X-ray diffraction Methods 0.000 description 18
- 238000010992 reflux Methods 0.000 description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 16
- 239000012458 free base Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 11
- 239000013543 active substance Substances 0.000 description 10
- 239000013078 crystal Substances 0.000 description 10
- 238000004090 dissolution Methods 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 230000009102 absorption Effects 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 8
- 238000002425 crystallisation Methods 0.000 description 8
- 230000008025 crystallization Effects 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 150000003840 hydrochlorides Chemical class 0.000 description 7
- 239000000843 powder Substances 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 238000002411 thermogravimetry Methods 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000013480 data collection Methods 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical group CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000011521 glass 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
- 239000000463 material Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000000425 proton nuclear magnetic resonance spectrum 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
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 238000005481 NMR spectroscopy 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
- 238000007707 calorimetry Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000010954 commercial manufacturing process Methods 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
- 230000010354 integration Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive 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
- 239000010431 corundum Substances 0.000 description 1
- 229910052593 corundum Inorganic materials 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000000113 differential scanning calorimetry 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
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 150000002500 ions Chemical group 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000003287 optical effect Effects 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
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000746 purification Methods 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
- 239000012453 solvate Substances 0.000 description 1
- 238000000935 solvent evaporation Methods 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
- 238000004846 x-ray emission Methods 0.000 description 1
Images
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 | |
| US61/225609 | 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 (3)
| Publication Number | Publication Date |
|---|---|
| BR112012000750A2 BR112012000750A2 (pt) | 2016-08-09 |
| BR112012000750A8 BR112012000750A8 (pt) | 2018-02-06 |
| BR112012000750B1 true BR112012000750B1 (pt) | 2021-05-25 |
Family
ID=42790728
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BR112012000750-5A BR112012000750B1 (pt) | 2009-07-15 | 2010-07-14 | sal citrato cristalino, composição farmacêutica compreendendo o referido sal e uso do mesmo |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US9062074B2 (enExample) |
| EP (1) | EP2454266B1 (enExample) |
| JP (2) | JP6013911B2 (enExample) |
| CN (1) | CN102762577B (enExample) |
| AR (2) | AR077483A1 (enExample) |
| BR (1) | BR112012000750B1 (enExample) |
| CA (1) | CA2768210C (enExample) |
| DK (1) | DK2454266T3 (enExample) |
| ES (1) | ES2429525T3 (enExample) |
| HR (1) | HRP20130941T1 (enExample) |
| MX (1) | MX2012000680A (enExample) |
| PL (1) | PL2454266T3 (enExample) |
| PT (1) | PT2454266E (enExample) |
| RU (1) | RU2543721C2 (enExample) |
| SI (1) | SI2454266T1 (enExample) |
| SM (1) | SMT201300112B (enExample) |
| TW (1) | TWI537276B (enExample) |
| WO (1) | WO2011008172A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2966753A1 (en) | 2014-11-17 | 2016-05-26 | Arno Therapeutics, Inc. | Onapristone extended-release compositions and methods |
| AU2016326657B2 (en) | 2015-09-25 | 2019-10-24 | Context Biopharma, Inc. | Methods of making onapristone intermediates |
| CA3008422A1 (en) | 2015-12-15 | 2017-06-22 | Context Biopharma Inc. | Amorphous onapristone compositions and methods of making the same |
| US20180148471A1 (en) | 2016-11-30 | 2018-05-31 | 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 |
| US7151096B2 (en) * | 2003-03-05 | 2006-12-19 | Irm Llc | Cyclic compounds and compositions as protein kinase inhibitors |
| CN101365703B (zh) * | 2005-11-16 | 2013-11-06 | S*Bio私人有限公司 | 杂烷基连接的嘧啶衍生物 |
-
2010
- 2010-07-14 EP EP10737645.1A patent/EP2454266B1/en active Active
- 2010-07-14 SI SI201030347T patent/SI2454266T1/sl unknown
- 2010-07-14 RU RU2012105044/04A patent/RU2543721C2/ru active
- 2010-07-14 PT PT107376451T patent/PT2454266E/pt unknown
- 2010-07-14 HR HRP20130941AT patent/HRP20130941T1/hr unknown
- 2010-07-14 BR BR112012000750-5A patent/BR112012000750B1/pt active IP Right Grant
- 2010-07-14 US US13/384,139 patent/US9062074B2/en active Active
- 2010-07-14 CN CN201080032627.5A patent/CN102762577B/zh active Active
- 2010-07-14 MX MX2012000680A patent/MX2012000680A/es active IP Right Grant
- 2010-07-14 PL PL10737645T patent/PL2454266T3/pl unknown
- 2010-07-14 ES ES10737645T patent/ES2429525T3/es active Active
- 2010-07-14 CA CA2768210A patent/CA2768210C/en active Active
- 2010-07-14 DK DK10737645.1T patent/DK2454266T3/da active
- 2010-07-14 JP JP2012520571A patent/JP6013911B2/ja active Active
- 2010-07-14 WO PCT/SG2010/000265 patent/WO2011008172A1/en not_active Ceased
- 2010-07-15 AR ARP100102594A patent/AR077483A1/es not_active Application Discontinuation
- 2010-07-15 TW TW099123331A patent/TWI537276B/zh active
-
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 |
|---|---|
| CN102762577A (zh) | 2012-10-31 |
| AR114987A2 (es) | 2020-11-11 |
| EP2454266A1 (en) | 2012-05-23 |
| JP2012533539A (ja) | 2012-12-27 |
| WO2011008172A1 (en) | 2011-01-20 |
| CA2768210C (en) | 2017-08-15 |
| ES2429525T3 (es) | 2013-11-15 |
| PL2454266T3 (pl) | 2014-01-31 |
| AR077483A1 (es) | 2011-08-31 |
| HRP20130941T1 (hr) | 2013-11-08 |
| MX2012000680A (es) | 2012-02-28 |
| BR112012000750A8 (pt) | 2018-02-06 |
| TWI537276B (zh) | 2016-06-11 |
| EP2454266B1 (en) | 2013-07-10 |
| CA2768210A1 (en) | 2011-01-20 |
| SI2454266T1 (sl) | 2013-10-30 |
| BR112012000750A2 (pt) | 2016-08-09 |
| SMT201300112B (it) | 2013-11-08 |
| JP2015164941A (ja) | 2015-09-17 |
| US9062074B2 (en) | 2015-06-23 |
| RU2012105044A (ru) | 2013-08-20 |
| HK1178159A1 (en) | 2013-09-06 |
| DK2454266T3 (da) | 2013-09-08 |
| TW201107336A (en) | 2011-03-01 |
| US20120196876A1 (en) | 2012-08-02 |
| RU2543721C2 (ru) | 2015-03-10 |
| JP6013911B2 (ja) | 2016-10-25 |
| CN102762577B (zh) | 2015-01-07 |
| PT2454266E (pt) | 2013-10-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B25C | Requirement related to requested transfer of rights |
Owner name: S*BIO PTE LTDA (SG) |
|
| B25A | Requested transfer of rights approved |
Owner name: CELL THERAPEUTICS, INC. (US) |
|
| B25D | Requested change of name of applicant approved |
Owner name: CTI BIOPHARMA CORP. (US) |
|
| B06F | Objections, documents and/or translations needed after an examination request according [chapter 6.6 patent gazette] | ||
| B07D | Technical examination (opinion) related to article 229 of industrial property law [chapter 7.4 patent gazette] |
Free format text: DE ACORDO COM O ARTIGO 229-C DA LEI NO 10196/2001, QUE MODIFICOU A LEI NO 9279/96, A CONCESSAO DA PATENTE ESTA CONDICIONADA A ANUENCIA PREVIA DA ANVISA. CONSIDERANDO A APROVACAO DOS TERMOS DO PARECER NO 337/PGF/EA/2010, BEM COMO A PORTARIA INTERMINISTERIAL NO 1065 DE 24/05/2012, ENCAMINHA-SE O PRESENTE PEDIDO PARA AS PROVIDENCIAS CABIVEIS. |
|
| B07E | Notification of approval relating to section 229 industrial property law [chapter 7.5 patent gazette] | ||
| B06U | Preliminary requirement: requests with searches performed by other patent offices: procedure suspended [chapter 6.21 patent gazette] | ||
| B07A | Application suspended after technical examination (opinion) [chapter 7.1 patent gazette] | ||
| B09A | Decision: intention to grant [chapter 9.1 patent gazette] | ||
| B16A | Patent or certificate of addition of invention granted [chapter 16.1 patent gazette] |
Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 14/07/2010, OBSERVADAS AS CONDICOES LEGAIS. PATENTE CONCEDIDA CONFORME ADI 5.529/DF |