JP2016527229A5 - - Google Patents
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- Publication number
- JP2016527229A5 JP2016527229A5 JP2016526997A JP2016526997A JP2016527229A5 JP 2016527229 A5 JP2016527229 A5 JP 2016527229A5 JP 2016526997 A JP2016526997 A JP 2016526997A JP 2016526997 A JP2016526997 A JP 2016526997A JP 2016527229 A5 JP2016527229 A5 JP 2016527229A5
- Authority
- JP
- Japan
- Prior art keywords
- octahydro
- dioxo
- benzamide
- trifluoromethyl
- ethenocycloprop
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 claims 14
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims 7
- 229920000642 polymer Polymers 0.000 claims 7
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims 6
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims 6
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims 6
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims 5
- 239000006193 liquid solution Substances 0.000 claims 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- 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 4
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims 4
- 239000007787 solid Substances 0.000 claims 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 3
- 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
- 238000001816 cooling Methods 0.000 claims 3
- 238000010438 heat treatment Methods 0.000 claims 3
- -1 methyl ether ketone Chemical class 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 239000007962 solid dispersion Substances 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- 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 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 2
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims 2
- 229920003091 Methocel™ Polymers 0.000 claims 2
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 claims 2
- 239000002202 Polyethylene glycol Substances 0.000 claims 2
- 229920001531 copovidone Polymers 0.000 claims 2
- LUJQXGBDWAGQHS-UHFFFAOYSA-N ethenyl acetate;phthalic acid Chemical compound CC(=O)OC=C.OC(=O)C1=CC=CC=C1C(O)=O LUJQXGBDWAGQHS-UHFFFAOYSA-N 0.000 claims 2
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims 2
- 229960003943 hypromellose Drugs 0.000 claims 2
- 238000002844 melting Methods 0.000 claims 2
- 230000008018 melting Effects 0.000 claims 2
- 229920003145 methacrylic acid copolymer Polymers 0.000 claims 2
- 150000004682 monohydrates Chemical class 0.000 claims 2
- 230000007935 neutral effect Effects 0.000 claims 2
- 229920001983 poloxamer Polymers 0.000 claims 2
- 229960000502 poloxamer Drugs 0.000 claims 2
- 229920001223 polyethylene glycol Polymers 0.000 claims 2
- 229920002744 polyvinyl acetate phthalate Polymers 0.000 claims 2
- 229940069328 povidone Drugs 0.000 claims 2
- 238000000634 powder X-ray diffraction Methods 0.000 claims 2
- 239000004094 surface-active agent Substances 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- VOJUXHHACRXLTD-UHFFFAOYSA-N 1,4-dihydroxy-2-naphthoic acid Chemical group C1=CC=CC2=C(O)C(C(=O)O)=CC(O)=C21 VOJUXHHACRXLTD-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 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
- 229920003072 Plasdone™ povidone Polymers 0.000 claims 1
- IYKJEILNJZQJPU-UHFFFAOYSA-N acetic acid;butanedioic acid Chemical compound CC(O)=O.OC(=O)CCC(O)=O IYKJEILNJZQJPU-UHFFFAOYSA-N 0.000 claims 1
- ZUAAPNNKRHMPKG-UHFFFAOYSA-N acetic acid;butanedioic acid;methanol;propane-1,2-diol Chemical compound OC.CC(O)=O.CC(O)CO.OC(=O)CCC(O)=O ZUAAPNNKRHMPKG-UHFFFAOYSA-N 0.000 claims 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 229920001577 copolymer Polymers 0.000 claims 1
- 239000006185 dispersion Substances 0.000 claims 1
- FYUWIEKAVLOHSE-UHFFFAOYSA-N ethenyl acetate;1-ethenylpyrrolidin-2-one Chemical compound CC(=O)OC=C.C=CN1CCCC1=O FYUWIEKAVLOHSE-UHFFFAOYSA-N 0.000 claims 1
- UHUSDOQQWJGJQS-UHFFFAOYSA-N glycerol 1,2-dioctadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(CO)OC(=O)CCCCCCCCCCCCCCCCC UHUSDOQQWJGJQS-UHFFFAOYSA-N 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 239000008389 polyethoxylated castor oil Substances 0.000 claims 1
- 229950008882 polysorbate Drugs 0.000 claims 1
- 229920000136 polysorbate Polymers 0.000 claims 1
- 238000001694 spray drying Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2020195121A JP7681393B2 (ja) | 2013-07-19 | 2020-11-25 | アモルファステコビリマット調製 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361856240P | 2013-07-19 | 2013-07-19 | |
| US61/856,240 | 2013-07-19 | ||
| PCT/US2014/046340 WO2015009566A1 (en) | 2013-07-19 | 2014-07-11 | Amorphous tecovirimat preparation |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020195121A Division JP7681393B2 (ja) | 2013-07-19 | 2020-11-25 | アモルファステコビリマット調製 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016527229A JP2016527229A (ja) | 2016-09-08 |
| JP2016527229A5 true JP2016527229A5 (https=) | 2017-08-24 |
| JP6843616B2 JP6843616B2 (ja) | 2021-03-17 |
Family
ID=52346653
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016526997A Active JP6843616B2 (ja) | 2013-07-19 | 2014-07-11 | アモルファステコビリマット調製 |
| JP2020195121A Active JP7681393B2 (ja) | 2013-07-19 | 2020-11-25 | アモルファステコビリマット調製 |
| JP2023065084A Pending JP2023080234A (ja) | 2013-07-19 | 2023-04-12 | アモルファステコビリマット調製 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020195121A Active JP7681393B2 (ja) | 2013-07-19 | 2020-11-25 | アモルファステコビリマット調製 |
| JP2023065084A Pending JP2023080234A (ja) | 2013-07-19 | 2023-04-12 | アモルファステコビリマット調製 |
Country Status (8)
| Country | Link |
|---|---|
| US (3) | US9670158B2 (https=) |
| EP (2) | EP3763702B1 (https=) |
| JP (3) | JP6843616B2 (https=) |
| CN (2) | CN111635353A (https=) |
| AU (1) | AU2014290333B2 (https=) |
| CA (3) | CA3246369A1 (https=) |
| IL (1) | IL242331B (https=) |
| WO (1) | WO2015009566A1 (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015009566A1 (en) * | 2013-07-19 | 2015-01-22 | Siga Technologies, Inc. | Amorphous tecovirimat preparation |
| CN107126419B (zh) * | 2016-02-26 | 2020-06-19 | 石药集团中诺药业（石家庄）有限公司 | 一种奥贝胆酸片剂及其制备方法 |
| CN112955130A (zh) * | 2018-10-30 | 2021-06-11 | 佩洛通治疗公司 | 包含取代茚满的固体分散体和药物组合物及其制备和使用方法 |
| CN115141136B (zh) * | 2021-03-31 | 2023-06-20 | 中国人民解放军军事科学院军事医学研究院 | 特考韦瑞药的共晶及其制备方法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PE20011184A1 (es) | 2000-03-16 | 2001-11-15 | Pfizer Prod Inc | Composiciones farmaceuticas de inhibidores de la glucogeno-fosforilasa |
| US6596771B2 (en) | 2001-01-12 | 2003-07-22 | Schering Corporation | Drugs for treating viral infections |
| US6433016B1 (en) | 2001-01-12 | 2002-08-13 | Vassil Stefanov Georgiev | Drugs for treating viral infections |
| 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 |
| EP1638938B1 (en) * | 2003-06-20 | 2017-04-12 | Siga Technologies Inc. | Compounds, compositions and methods for treatment and prevention of orthopoxvirus infections and associated diseases |
| US8642577B2 (en) * | 2005-04-08 | 2014-02-04 | Chimerix, Inc. | Compounds, compositions and methods for the treatment of poxvirus infections |
| JP2010526848A (ja) * | 2007-05-11 | 2010-08-05 | エフ．ホフマン−ラ ロシュ アーゲー | 難溶性薬物用の医薬組成物 |
| JP6018041B2 (ja) | 2010-03-23 | 2016-11-02 | シガ・テクノロジーズ・インコーポレーテッド | Ｓｔ−２４６の多形型および調製方法 |
| BR112012031516A2 (pt) * | 2010-06-09 | 2016-11-08 | Abbott Lab | dispersões sólidas contendo inibidores de quinase |
| GB201103837D0 (en) * | 2011-03-07 | 2011-04-20 | Oxagen Ltd | Amorphous (5-Fluoro-2-Methyl-3-Quinolin-2-Ylmethyl-Indol-1-Yl)-acetic acid |
| US8591944B2 (en) * | 2011-03-08 | 2013-11-26 | Zalicus Pharmaceuticals Ltd. | Solid dispersion formulations and methods of use thereof |
| WO2013056108A2 (en) * | 2011-10-14 | 2013-04-18 | Array Biopharma Inc. | Solid dispersion |
| JP2013103899A (ja) * | 2011-11-11 | 2013-05-30 | Fuji Chem Ind Co Ltd | 難溶性薬物の新規な固体分散体 |
| CN102406617B (zh) * | 2011-11-30 | 2013-08-28 | 中国人民解放军军事医学科学院生物工程研究所 | 一种替韦立马干混悬剂及其制备方法 |
| WO2015009566A1 (en) | 2013-07-19 | 2015-01-22 | Siga Technologies, Inc. | Amorphous tecovirimat preparation |
-
2014
- 2014-07-11 WO PCT/US2014/046340 patent/WO2015009566A1/en not_active Ceased
- 2014-07-11 CA CA3246369A patent/CA3246369A1/en active Pending
- 2014-07-11 CA CA3128535A patent/CA3128535C/en active Active
- 2014-07-11 CA CA2917199A patent/CA2917199C/en active Active
- 2014-07-11 CN CN202010516675.7A patent/CN111635353A/zh active Pending
- 2014-07-11 EP EP20190932.2A patent/EP3763702B1/en active Active
- 2014-07-11 AU AU2014290333A patent/AU2014290333B2/en active Active
- 2014-07-11 JP JP2016526997A patent/JP6843616B2/ja active Active
- 2014-07-11 EP EP14825621.7A patent/EP3021836B1/en active Active
- 2014-07-11 CN CN201480026785.8A patent/CN105307636A/zh active Pending
- 2014-07-11 US US14/903,083 patent/US9670158B2/en active Active
-
2015
- 2015-10-29 IL IL242331A patent/IL242331B/en active IP Right Grant
-
2017
- 2017-04-27 US US15/498,787 patent/US9889119B2/en active Active
-
2018
- 2018-01-02 US US15/860,262 patent/US10045963B2/en active Active
-
2020
- 2020-11-25 JP JP2020195121A patent/JP7681393B2/ja active Active
-
2023
- 2023-04-12 JP JP2023065084A patent/JP2023080234A/ja active Pending
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