CA2930461C - Rehydration of micronized tecovirimat monohydrate - Google Patents
Rehydration of micronized tecovirimat monohydrate Download PDFInfo
- Publication number
- CA2930461C CA2930461C CA2930461A CA2930461A CA2930461C CA 2930461 C CA2930461 C CA 2930461C CA 2930461 A CA2930461 A CA 2930461A CA 2930461 A CA2930461 A CA 2930461A CA 2930461 C CA2930461 C CA 2930461C
- Authority
- CA
- Canada
- Prior art keywords
- particles
- moisture
- monohydrate
- polymorph form
- polymorph
- 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
- CSKDFZIMJXRJGH-VWLPUNTISA-N tecovirimat Chemical compound C1=CC(C(F)(F)F)=CC=C1C(=O)NN1C(=O)[C@@H]([C@@H]2[C@H]3C[C@H]3[C@H]3C=C2)[C@@H]3C1=O CSKDFZIMJXRJGH-VWLPUNTISA-N 0.000 title claims abstract description 87
- 239000002245 particle Substances 0.000 claims abstract description 89
- 238000000034 method Methods 0.000 claims abstract description 50
- 230000008569 process Effects 0.000 claims description 24
- 150000004682 monohydrates Chemical class 0.000 claims description 20
- 238000001035 drying Methods 0.000 claims description 9
- 238000002156 mixing Methods 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000012530 fluid Substances 0.000 claims description 6
- 238000009478 high shear granulation Methods 0.000 claims description 5
- 230000000887 hydrating effect Effects 0.000 claims description 4
- 230000001419 dependent effect Effects 0.000 claims 2
- 238000007873 sieving Methods 0.000 claims 2
- 230000036571 hydration Effects 0.000 abstract description 5
- 238000006703 hydration reaction Methods 0.000 abstract description 5
- 239000003570 air Substances 0.000 description 27
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- QRHXYGPOQKLBJP-NPIFKJBVSA-N sb96yo2br8 Chemical compound O.C1=CC(C(F)(F)F)=CC=C1C(=O)NN1C(=O)[C@@H]([C@@H]2[C@H]3C[C@H]3[C@H]3C=C2)[C@@H]3C1=O QRHXYGPOQKLBJP-NPIFKJBVSA-N 0.000 description 10
- VWFCHDSQECPREK-LURJTMIESA-N Cidofovir Chemical compound NC=1C=CN(C[C@@H](CO)OCP(O)(O)=O)C(=O)N=1 VWFCHDSQECPREK-LURJTMIESA-N 0.000 description 9
- 229960000724 cidofovir Drugs 0.000 description 9
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- DLGSOJOOYHWROO-WQLSENKSSA-N [(z)-(1-methyl-2-oxoindol-3-ylidene)amino]thiourea Chemical compound C1=CC=C2N(C)C(=O)\C(=N/NC(N)=S)C2=C1 DLGSOJOOYHWROO-WQLSENKSSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
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- 241000700625 Poxviridae Species 0.000 description 2
- ZJUKTBDSGOFHSH-WFMPWKQPSA-N S-Adenosylhomocysteine Chemical compound O[C@@H]1[C@H](O)[C@@H](CSCC[C@H](N)C(O)=O)O[C@H]1N1C2=NC=NC(N)=C2N=C1 ZJUKTBDSGOFHSH-WFMPWKQPSA-N 0.000 description 2
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- FFFHZYDWPBMWHY-VKHMYHEASA-N L-homocysteine Chemical compound OC(=O)[C@@H](N)CCS FFFHZYDWPBMWHY-VKHMYHEASA-N 0.000 description 1
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- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
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- 230000010006 flight Effects 0.000 description 1
- 238000005243 fluidization Methods 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 230000002008 hemorrhagic effect Effects 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 230000036543 hypotension Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
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- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 230000007694 nephrotoxicity Effects 0.000 description 1
- 231100000417 nephrotoxicity Toxicity 0.000 description 1
- 125000003835 nucleoside group Chemical group 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 235000012771 pancakes Nutrition 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 238000011020 pilot scale process Methods 0.000 description 1
- 238000001907 polarising light microscopy Methods 0.000 description 1
- 238000012809 post-inoculation Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
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- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 description 1
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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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
-
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/4035—Isoindoles, e.g. phthalimide
-
- 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
- A61K9/1682—Processes
- A61K9/1688—Processes resulting in pure drug agglomerate optionally containing up to 5% of excipient
-
- 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
- A61P31/12—Antivirals
-
- 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
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Virology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361906119P | 2013-11-19 | 2013-11-19 | |
| US61/906,119 | 2013-11-19 | ||
| PCT/US2014/065674 WO2015077143A1 (en) | 2013-11-19 | 2014-11-14 | Rehydration of micronized tecovirimat monohydrate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2930461A1 CA2930461A1 (en) | 2015-05-28 |
| CA2930461C true CA2930461C (en) | 2022-08-16 |
Family
ID=53180052
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2930461A Active CA2930461C (en) | 2013-11-19 | 2014-11-14 | Rehydration of micronized tecovirimat monohydrate |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US10406103B2 (enExample) |
| EP (1) | EP3043793B1 (enExample) |
| JP (1) | JP6594303B2 (enExample) |
| CN (1) | CN105636585B (enExample) |
| AU (2) | AU2014353235B2 (enExample) |
| CA (1) | CA2930461C (enExample) |
| IL (2) | IL244731B (enExample) |
| WO (1) | WO2015077143A1 (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020252284A1 (en) * | 2019-06-13 | 2020-12-17 | Imbucanna, Inc | Compressible cannabinoid pharmaceutical composition |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10232113A1 (de) * | 2002-07-16 | 2004-01-29 | Bayer Ag | Vardenafil Hydrochlorid Trihydrat enthaltende Arzneimittel |
| US7687641B2 (en) * | 2003-06-20 | 2010-03-30 | Siga Technologies, Inc. | Chemicals, compositions, and methods for treatment and prevention of orthopoxvirus infections and associated diseases |
| US7737168B2 (en) * | 2003-06-20 | 2010-06-15 | Siga Technologies, Inc. | Compounds, compositions, and methods for treatment and prevention of orthopoxvirus infections and associated diseases |
| UA97349C2 (uk) * | 2005-09-08 | 2012-02-10 | Х. Луннбэк А/С | Стійкі тверді склади сертиндолу |
| CA2685153C (en) * | 2007-04-23 | 2014-12-16 | Siga Technologies, Inc. | Chemicals, compositions, and methods for treatment and prevention of orthopoxvirus infections and associated diseases |
| CN101445478B (zh) | 2008-08-22 | 2011-04-06 | 中国人民解放军军事医学科学院生物工程研究所 | 含一个结晶水的化合物st-246及其晶体与制备方法 |
| JP2011041888A (ja) * | 2009-08-20 | 2011-03-03 | Nippon Soda Co Ltd | ジェットミル粉砕条件の最適化方法 |
| EP2549871B1 (en) * | 2010-03-23 | 2018-08-22 | Siga Technologies, Inc. | Polymorphic form st-246 and methods of preparation |
| SG10202105262QA (en) * | 2010-08-05 | 2021-06-29 | Siga Technologies Inc | St-246 liquid formulations and methods |
-
2014
- 2014-11-14 US US15/027,557 patent/US10406103B2/en active Active
- 2014-11-14 AU AU2014353235A patent/AU2014353235B2/en active Active
- 2014-11-14 CN CN201480056338.7A patent/CN105636585B/zh active Active
- 2014-11-14 WO PCT/US2014/065674 patent/WO2015077143A1/en not_active Ceased
- 2014-11-14 CA CA2930461A patent/CA2930461C/en active Active
- 2014-11-14 JP JP2016522728A patent/JP6594303B2/ja active Active
- 2014-11-14 EP EP14863672.3A patent/EP3043793B1/en active Active
-
2016
- 2016-03-23 IL IL244731A patent/IL244731B/en active IP Right Grant
-
2019
- 2019-07-23 US US16/519,815 patent/US10716759B2/en active Active
- 2019-07-26 AU AU2019208252A patent/AU2019208252B2/en active Active
-
2021
- 2021-04-06 IL IL282098A patent/IL282098B2/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL282098A (en) | 2021-05-31 |
| CN105636585B (zh) | 2020-02-07 |
| EP3043793A1 (en) | 2016-07-20 |
| JP2016537318A (ja) | 2016-12-01 |
| EP3043793B1 (en) | 2021-01-06 |
| CN105636585A (zh) | 2016-06-01 |
| AU2014353235A1 (en) | 2016-04-21 |
| JP6594303B2 (ja) | 2019-10-23 |
| CA2930461A1 (en) | 2015-05-28 |
| IL282098B1 (en) | 2023-01-01 |
| AU2019208252B2 (en) | 2020-03-19 |
| WO2015077143A1 (en) | 2015-05-28 |
| AU2014353235B2 (en) | 2019-05-09 |
| US10716759B2 (en) | 2020-07-21 |
| IL244731A0 (en) | 2016-04-21 |
| US10406103B2 (en) | 2019-09-10 |
| US20160235676A1 (en) | 2016-08-18 |
| IL244731B (en) | 2021-05-31 |
| IL282098B2 (en) | 2023-05-01 |
| EP3043793A4 (en) | 2017-05-10 |
| US20190380966A1 (en) | 2019-12-19 |
| AU2019208252A1 (en) | 2019-08-15 |
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