RU2016149485A - Твердые формы ромидепсина и их применение - Google Patents
Твердые формы ромидепсина и их применение Download PDFInfo
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- RU2016149485A RU2016149485A RU2016149485A RU2016149485A RU2016149485A RU 2016149485 A RU2016149485 A RU 2016149485A RU 2016149485 A RU2016149485 A RU 2016149485A RU 2016149485 A RU2016149485 A RU 2016149485A RU 2016149485 A RU2016149485 A RU 2016149485A
- Authority
- RU
- Russia
- Prior art keywords
- cellulose
- romidepsin
- amorphous
- amorphous romidepsin
- derivative
- Prior art date
Links
- OHRURASPPZQGQM-GCCNXGTGSA-N romidepsin Chemical compound O1C(=O)[C@H](C(C)C)NC(=O)C(=C/C)/NC(=O)[C@H]2CSSCC\C=C\[C@@H]1CC(=O)N[C@H](C(C)C)C(=O)N2 OHRURASPPZQGQM-GCCNXGTGSA-N 0.000 title claims 12
- 229960003452 romidepsin Drugs 0.000 title claims 12
- OHRURASPPZQGQM-UHFFFAOYSA-N romidepsin Natural products O1C(=O)C(C(C)C)NC(=O)C(=CC)NC(=O)C2CSSCCC=CC1CC(=O)NC(C(C)C)C(=O)N2 OHRURASPPZQGQM-UHFFFAOYSA-N 0.000 title claims 12
- 108010091666 romidepsin Proteins 0.000 title claims 12
- 239000007787 solid Substances 0.000 title 1
- 239000000203 mixture Substances 0.000 claims 6
- 229920002678 cellulose Polymers 0.000 claims 4
- 239000001913 cellulose Substances 0.000 claims 4
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims 4
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims 3
- 229920000642 polymer Polymers 0.000 claims 3
- 208000027190 Peripheral T-cell lymphomas Diseases 0.000 claims 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims 2
- 208000031673 T-Cell Cutaneous Lymphoma Diseases 0.000 claims 2
- 208000031672 T-Cell Peripheral Lymphoma Diseases 0.000 claims 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 claims 2
- 239000001768 carboxy methyl cellulose Substances 0.000 claims 2
- 201000007241 cutaneous T cell lymphoma Diseases 0.000 claims 2
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims 2
- 208000020968 mature T-cell and NK-cell non-Hodgkin lymphoma Diseases 0.000 claims 2
- 201000005962 mycosis fungoides Diseases 0.000 claims 2
- 229920001223 polyethylene glycol Polymers 0.000 claims 2
- 208000025638 primary cutaneous T-cell non-Hodgkin lymphoma Diseases 0.000 claims 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 claims 2
- 150000005846 sugar alcohols Chemical class 0.000 claims 2
- 238000002411 thermogravimetry Methods 0.000 claims 2
- -1 vinyl lactam Chemical class 0.000 claims 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims 1
- 229920000858 Cyclodextrin Polymers 0.000 claims 1
- 229920002307 Dextran Polymers 0.000 claims 1
- 239000001856 Ethyl cellulose Substances 0.000 claims 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 claims 1
- 108010010803 Gelatin Proteins 0.000 claims 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 claims 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 claims 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims 1
- 239000004698 Polyethylene Substances 0.000 claims 1
- 239000002202 Polyethylene glycol Substances 0.000 claims 1
- 239000004372 Polyvinyl alcohol Substances 0.000 claims 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical class CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- 239000011575 calcium Substances 0.000 claims 1
- 229910052791 calcium Inorganic materials 0.000 claims 1
- 235000001465 calcium Nutrition 0.000 claims 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 claims 1
- 229920003123 carboxymethyl cellulose sodium Polymers 0.000 claims 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 claims 1
- 229940105329 carboxymethylcellulose Drugs 0.000 claims 1
- 229940063834 carboxymethylcellulose sodium Drugs 0.000 claims 1
- 229920001249 ethyl cellulose Polymers 0.000 claims 1
- 235000019325 ethyl cellulose Nutrition 0.000 claims 1
- 229920000159 gelatin Polymers 0.000 claims 1
- 239000008273 gelatin Substances 0.000 claims 1
- 235000019322 gelatine Nutrition 0.000 claims 1
- 235000011852 gelatine desserts Nutrition 0.000 claims 1
- 230000009477 glass transition Effects 0.000 claims 1
- 229920000591 gum Polymers 0.000 claims 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 claims 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims 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 claims 1
- 229960003943 hypromellose Drugs 0.000 claims 1
- 229920003145 methacrylic acid copolymer Polymers 0.000 claims 1
- 229940117841 methacrylic acid copolymer Drugs 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 claims 1
- 229920000573 polyethylene Polymers 0.000 claims 1
- 229920000136 polysorbate Polymers 0.000 claims 1
- 229920002451 polyvinyl alcohol Polymers 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- 238000000634 powder X-ray diffraction Methods 0.000 claims 1
- VORWPIMQKSQGDA-UHFFFAOYSA-N propan-2-ol 2,2,2-trifluoroethanol Chemical compound FC(CO)(F)F.C(C)(C)O VORWPIMQKSQGDA-UHFFFAOYSA-N 0.000 claims 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 claims 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 claims 1
- 238000001757 thermogravimetry curve Methods 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K11/00—Depsipeptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K11/02—Depsipeptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof cyclic, e.g. valinomycins ; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/07—Tetrapeptides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/15—Depsipeptides; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/10—Tetrapeptides
- C07K5/1002—Tetrapeptides with the first amino acid being neutral
- C07K5/1005—Tetrapeptides with the first amino acid being neutral and aliphatic
- C07K5/101—Tetrapeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms, e.g. Val, Ile, Leu
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Gastroenterology & Hepatology (AREA)
- Epidemiology (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Diabetes (AREA)
- Dermatology (AREA)
- Transplantation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Claims (11)
1. Аморфный ромидепсин.
2. Аморфный ромидепсин по п.1, характеризующийся порошковой рентгеновской дифрактограммой (XRPD), по существу такой как показано на Фиг.7(а).
3. Аморфный ромидепсин по п.2, где аморфный ромидепсин получают из смеси вода/дихлорметан.
4. Аморфный ромидепсин по п.2, где аморфный ромидепсин получают из смеси изопропанол-трифторэтанол/метанол.
5. Аморфный ромидепсин по любому из пп.1-4, где аморфный ромидепсин имеет температуру стеклования около 91oC.
6. Аморфный ромидепсин по любому из пп.1-4, где термограмма термогравиметрического анализа (TГA) демонстрирует потерю массы 3,5%.
7. Композиция, содержащая аморфный ромидепсин по п.1 и эксципиент, где эксципиент выбирают из группы, состоящей из производного целлюлозы, камеди, декстрана, виниллактама, циклодекстрина, желатина, фталата гипромеллозы, сахарного спирта, многоатомного спирта, полимера полиэтиленгликоля (ПЭГ), полиэтиленоксида, производного полиэтилена, поливинилового спирта, производного пропиленгликоля, лаурилсульфата натрия (SLS), твина, сополимера метакриловой кислоты, и аминокислоты.
8. Композиция по п.7, где эксципиент представляет собой производное целлюлозы.
9. Композиция по п.8, где производное целлюлозы представляет собой полимер гидроксипропилметилцеллюлозы (ГПМЦ), гидроксипропилцеллюлозу, этилцеллюлозу, гидроксиэтилцеллюлозу, карбоксиметилцеллюлозу натрия, кальцийкарбоксиметилцеллюлозу, или натриевую соль карбоксиметилцеллюлозы.
10. Композиция по п.9, где производное целлюлозы представляет собой полимер ГПМЦ.
11. Применение аморфного ромидепсина по любому из пп.1-6 в способе лечения кожной Т-клеточной лимфомы (CTCL) или периферической Т-клеточной лимфомы (PPCL).
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36352210P | 2010-07-12 | 2010-07-12 | |
| US61/363,522 | 2010-07-12 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2013105700A Division RU2607634C2 (ru) | 2010-07-12 | 2011-07-12 | Твердые формы ромидепсина и их применение |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2016149485A true RU2016149485A (ru) | 2018-10-31 |
Family
ID=44514993
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2016149485A RU2016149485A (ru) | 2010-07-12 | 2011-07-12 | Твердые формы ромидепсина и их применение |
| RU2013105700A RU2607634C2 (ru) | 2010-07-12 | 2011-07-12 | Твердые формы ромидепсина и их применение |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2013105700A RU2607634C2 (ru) | 2010-07-12 | 2011-07-12 | Твердые формы ромидепсина и их применение |
Country Status (16)
| Country | Link |
|---|---|
| US (5) | US20120190817A2 (ru) |
| EP (1) | EP2593123B1 (ru) |
| JP (3) | JP6049614B2 (ru) |
| KR (1) | KR20130092557A (ru) |
| CN (1) | CN103108648A (ru) |
| AU (1) | AU2011279303B2 (ru) |
| BR (1) | BR112013000673A2 (ru) |
| CA (1) | CA2804795A1 (ru) |
| ES (1) | ES2755909T3 (ru) |
| MX (1) | MX342913B (ru) |
| MY (1) | MY185130A (ru) |
| NZ (2) | NZ706052A (ru) |
| RU (2) | RU2016149485A (ru) |
| SG (2) | SG10201505475XA (ru) |
| UA (1) | UA114074C2 (ru) |
| WO (1) | WO2012009336A1 (ru) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2007342030B2 (en) * | 2006-12-29 | 2013-08-15 | Celgene Corporation | Romidepsin-based treatments for cancer |
| DE102011090178A1 (de) * | 2011-12-30 | 2013-07-04 | Lts Lohmann Therapie-Systeme Ag | Transdermales therapeutisches System mit geringer Neigung zur Spontankristallisation |
| US20130184225A1 (en) | 2012-01-12 | 2013-07-18 | Lianfeng Huang | Romidepsin formulations and uses thereof |
| AU2013202506B2 (en) | 2012-09-07 | 2015-06-18 | Celgene Corporation | Resistance biomarkers for hdac inhibitors |
| CN103877010B (zh) * | 2012-12-21 | 2018-06-01 | 正大天晴药业集团股份有限公司 | 一种罗米地辛溶液的制备方法 |
| WO2014102731A1 (en) * | 2012-12-31 | 2014-07-03 | Leiutis Pharmaceuticals Pvt. Ltd | Novel pharmaceutical compositions of romidepsin |
| ITMI20131856A1 (it) * | 2013-11-08 | 2015-05-09 | Gnosis Spa | Processo per la preparazione di differenti forme cristalline del s-acetil glutatione e loro utilizzi in formulazioni farmaceutiche e nutraceutiche |
| CN103861084A (zh) * | 2014-02-12 | 2014-06-18 | 新乡医学院 | Romidepsin在治疗帕金森病中的应用 |
| CN104262456B (zh) * | 2014-09-11 | 2018-01-09 | 浙江海正药业股份有限公司 | 一种罗米地辛的新晶型及其制备方法和用途 |
| JP6980534B2 (ja) | 2015-06-25 | 2021-12-15 | ザ チルドレンズ メディカル センター コーポレーション | 造血幹細胞の増大、富化、および維持に関する方法および組成物 |
| EP3429603B1 (en) | 2016-03-15 | 2021-12-29 | Children's Medical Center Corporation | Methods and compositions relating to hematopoietic stem cell expansion |
| CN105801667B (zh) * | 2016-03-22 | 2019-04-09 | 浙江海正药业股份有限公司 | 一种制备无定型罗米地辛的方法 |
| RU2019118985A (ru) * | 2016-11-22 | 2020-12-25 | Алкалидэкс, Инк. | Препараты для лечения устойчивых к действию лидокаина и гипокалиемических состояний |
| CN109796521B (zh) * | 2017-11-17 | 2022-04-19 | 上海医药工业研究院 | 一种罗米地辛醋酸盐晶型及其制备方法 |
| CN111187337B (zh) * | 2018-11-15 | 2023-01-24 | 上海医药工业研究院 | 罗米地辛一异丙醇溶剂合物及其晶型、制备方法和应用 |
| WO2020139453A2 (en) * | 2018-12-24 | 2020-07-02 | Marrone Bio Innovations, Inc. | A method for increasing romidepsin production from fermentation broth |
| WO2021253338A1 (zh) * | 2020-06-18 | 2021-12-23 | 中国科学院深圳先进技术研究院 | 罗米地辛在预防和治疗冠状病毒相关疾病中的应用 |
| CN113813366A (zh) * | 2020-06-18 | 2021-12-21 | 中国科学院深圳先进技术研究院 | 罗米地辛在制备预防和治疗抗新冠肺炎新型冠状病毒的药物中的应用 |
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