JP2015509941A5 - - Google Patents
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- Publication number
- JP2015509941A5 JP2015509941A5 JP2014557840A JP2014557840A JP2015509941A5 JP 2015509941 A5 JP2015509941 A5 JP 2015509941A5 JP 2014557840 A JP2014557840 A JP 2014557840A JP 2014557840 A JP2014557840 A JP 2014557840A JP 2015509941 A5 JP2015509941 A5 JP 2015509941A5
- Authority
- JP
- Japan
- Prior art keywords
- pharmaceutical composition
- laquinimod
- ethyl
- methyl
- pharmaceutically acceptable
- 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
- 239000008194 pharmaceutical composition Substances 0.000 claims description 64
- 238000000034 method Methods 0.000 claims description 56
- GKWPCEFFIHSJOE-UHFFFAOYSA-N laquinimod Chemical compound OC=1C2=C(Cl)C=CC=C2N(C)C(=O)C=1C(=O)N(CC)C1=CC=CC=C1 GKWPCEFFIHSJOE-UHFFFAOYSA-N 0.000 claims description 53
- 229960004577 laquinimod Drugs 0.000 claims description 53
- 150000003839 salts Chemical class 0.000 claims description 36
- YFDWFVLGERLACT-UHFFFAOYSA-N n-ethyl-4,5-dihydroxy-1-methyl-2-oxo-n-phenylquinoline-3-carboxamide Chemical compound OC=1C2=C(O)C=CC=C2N(C)C(=O)C=1C(=O)N(CC)C1=CC=CC=C1 YFDWFVLGERLACT-UHFFFAOYSA-N 0.000 claims description 27
- 239000005022 packaging material Substances 0.000 claims description 17
- 239000003937 drug carrier Substances 0.000 claims description 13
- 229920001903 high density polyethylene Polymers 0.000 claims description 13
- 239000004700 high-density polyethylene Substances 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 12
- 239000011248 coating agent Substances 0.000 claims description 12
- 238000000576 coating method Methods 0.000 claims description 12
- -1 3-quinolinecarboxamide Carboxamide Chemical class 0.000 claims description 10
- 239000008187 granular material Substances 0.000 claims description 8
- 239000000243 solution Substances 0.000 claims description 8
- 238000013112 stability test Methods 0.000 claims description 8
- 201000006417 multiple sclerosis Diseases 0.000 claims description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 6
- 229910052782 aluminium Inorganic materials 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 238000004806 packaging method and process Methods 0.000 claims description 6
- 239000002841 Lewis acid Substances 0.000 claims description 4
- 239000004743 Polypropylene Substances 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 239000003637 basic solution Substances 0.000 claims description 4
- 239000002775 capsule Substances 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 150000007517 lewis acids Chemical class 0.000 claims description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical group [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 229920001155 polypropylene Polymers 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 239000004408 titanium dioxide Substances 0.000 claims description 3
- 229920000219 Ethylene vinyl alcohol Polymers 0.000 claims description 2
- 239000004698 Polyethylene Substances 0.000 claims description 2
- 229920001328 Polyvinylidene chloride Polymers 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- 239000002274 desiccant Substances 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 239000004715 ethylene vinyl alcohol Substances 0.000 claims description 2
- RZXDTJIXPSCHCI-UHFFFAOYSA-N hexa-1,5-diene-2,5-diol Chemical compound OC(=C)CCC(O)=C RZXDTJIXPSCHCI-UHFFFAOYSA-N 0.000 claims description 2
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 2
- 230000006698 induction Effects 0.000 claims description 2
- 235000019359 magnesium stearate Nutrition 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 229940124531 pharmaceutical excipient Drugs 0.000 claims description 2
- 239000004417 polycarbonate Substances 0.000 claims description 2
- 229920000515 polycarbonate Polymers 0.000 claims description 2
- 239000005023 polychlorotrifluoroethylene (PCTFE) polymer Substances 0.000 claims description 2
- 229920000573 polyethylene Polymers 0.000 claims description 2
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 2
- 239000004800 polyvinyl chloride Substances 0.000 claims description 2
- 239000005033 polyvinylidene chloride Substances 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- BLTDCIWCFCUQCB-UHFFFAOYSA-N quinoline-3-carboxamide Chemical compound C1=CC=CC2=CC(C(=O)N)=CN=C21 BLTDCIWCFCUQCB-UHFFFAOYSA-N 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 2
- OMEMVUCWXVDOSI-UHFFFAOYSA-N 4-methyl-2-oxo-1h-quinoline-3-carboxamide Chemical compound C1=CC=C2C(C)=C(C(N)=O)C(=O)NC2=C1 OMEMVUCWXVDOSI-UHFFFAOYSA-N 0.000 claims 1
- ZEXKKIXCRDTKBF-UHFFFAOYSA-N quinoline-2-carboxamide Chemical compound C1=CC=CC2=NC(C(=O)N)=CC=C21 ZEXKKIXCRDTKBF-UHFFFAOYSA-N 0.000 claims 1
- 238000012430 stability testing Methods 0.000 claims 1
- MYVHMGNKBVYIBT-UHFFFAOYSA-N 2-oxo-1h-quinoline-3-carboxamide Chemical compound C1=CC=C2NC(=O)C(C(=O)N)=CC2=C1 MYVHMGNKBVYIBT-UHFFFAOYSA-N 0.000 description 3
- 159000000000 sodium salts Chemical group 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- CTWUMQYEFABQRP-UHFFFAOYSA-N 1-methyl-2-oxoquinoline-3-carboxamide Chemical compound C1=CC=C2C=C(C(N)=O)C(=O)N(C)C2=C1 CTWUMQYEFABQRP-UHFFFAOYSA-N 0.000 description 1
- ASJSMVVSULIEER-UHFFFAOYSA-N 4,5-dihydroxy-1-methyl-2-oxoquinoline-3-carboxamide Chemical compound C1=CC(O)=C2C(O)=C(C(N)=O)C(=O)N(C)C2=C1 ASJSMVVSULIEER-UHFFFAOYSA-N 0.000 description 1
- TUWMPKGHCJTRFQ-UHFFFAOYSA-N 6-ethyl-4,5-dihydroxy-1-methyl-2-oxo-N-phenylquinoline-3-carboxamide Chemical compound C(C)C=1C(=C2C(=C(C(N(C2=CC=1)C)=O)C(=O)NC1=CC=CC=C1)O)O TUWMPKGHCJTRFQ-UHFFFAOYSA-N 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940126534 drug product Drugs 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000002831 pharmacologic agent Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261599680P | 2012-02-16 | 2012-02-16 | |
| US61/599,680 | 2012-02-16 | ||
| PCT/US2013/026476 WO2013123419A1 (en) | 2012-02-16 | 2013-02-15 | N-ethyl-n-phenyl-1,2-dihydro-4,5-di-hydroxy-1-methyl-2-oxo-3-quinoline carboxamide, preparation and uses thereof |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017138167A Division JP2018008965A (ja) | 2012-02-16 | 2017-07-14 | Ｎ−エチル−ｎ−フェニル−１，２−ジヒドロ−４，５−ジ−ヒドロキシ−１−メチル−２−オキソ−３−キノリンカルボキサミド、その製剤、および使用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015509941A JP2015509941A (ja) | 2015-04-02 |
| JP2015509941A5 true JP2015509941A5 (https=) | 2016-04-07 |
| JP6215238B2 JP6215238B2 (ja) | 2017-10-18 |
Family
ID=48982733
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014557840A Expired - Fee Related JP6215238B2 (ja) | 2012-02-16 | 2013-02-15 | Ｎ−エチル−ｎ−フェニル−１，２−ジヒドロ−４，５−ジ−ヒドロキシ−１−メチル−２−オキソ−３−キノリンカルボキサミド、その製剤、および使用 |
| JP2017138167A Withdrawn JP2018008965A (ja) | 2012-02-16 | 2017-07-14 | Ｎ−エチル−ｎ−フェニル−１，２−ジヒドロ−４，５−ジ−ヒドロキシ−１−メチル−２−オキソ−３−キノリンカルボキサミド、その製剤、および使用 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017138167A Withdrawn JP2018008965A (ja) | 2012-02-16 | 2017-07-14 | Ｎ−エチル−ｎ−フェニル−１，２−ジヒドロ−４，５−ジ−ヒドロキシ−１−メチル−２−オキソ−３−キノリンカルボキサミド、その製剤、および使用 |
Country Status (17)
| Country | Link |
|---|---|
| US (4) | US9284276B2 (https=) |
| EP (2) | EP3225617A1 (https=) |
| JP (2) | JP6215238B2 (https=) |
| KR (1) | KR20140138725A (https=) |
| CN (1) | CN104114172A (https=) |
| AR (1) | AR090073A1 (https=) |
| AU (1) | AU2013221304B2 (https=) |
| BR (1) | BR112014020372A8 (https=) |
| CA (1) | CA2863409A1 (https=) |
| EA (1) | EA201491517A1 (https=) |
| HK (1) | HK1198296A1 (https=) |
| IL (1) | IL233556A0 (https=) |
| MX (1) | MX2014009889A (https=) |
| SG (1) | SG11201404419WA (https=) |
| TW (1) | TW201339137A (https=) |
| WO (1) | WO2013123419A1 (https=) |
| ZA (1) | ZA201406492B (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106344576A (zh) | 2011-10-12 | 2017-01-25 | 泰华制药工业有限公司 | 以拉喹莫德和芬戈莫德的组合治疗多发性硬化症 |
| CN106063787A (zh) | 2012-02-03 | 2016-11-02 | 泰华制药工业有限公司 | 拉喹莫德用于治疗一线抗TNFα疗法失败的克罗恩氏病患者的用途 |
| TW201400117A (zh) | 2012-06-05 | 2014-01-01 | Teva Pharma | 使用拉喹莫德治療眼發炎疾病 |
| TW201410244A (zh) | 2012-08-13 | 2014-03-16 | Teva Pharma | 用於治療ｇａｂａ媒介之疾病之拉喹莫德（ｌａｑｕｉｎｉｍｏｄ） |
| JP2015535287A (ja) | 2012-11-07 | 2015-12-10 | テバ ファーマシューティカル インダストリーズ リミティド | ラキニモドのアミン塩 |
| NZ630427A (en) | 2013-03-14 | 2017-06-30 | Teva Pharma | Crystals of laquinimod sodium and improved process for the manufacture thereof |
| EA201692180A1 (ru) | 2014-04-29 | 2017-08-31 | Тева Фармасьютикал Индастриз Лтд. | Лахинимод для лечения пациентов с рецидивирующе-ремиттирующим рассеянным склерозом (рррс) с высоким статусом инвалидизации |
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| RS54328B1 (sr) | 2009-06-19 | 2016-02-29 | Teva Pharmaceutical Industries Ltd. | Tretman multiple skleroze lakvinimodom |
| ME02414B (me) | 2009-07-30 | 2016-09-20 | Teva Pharma | Tretman kronove bolesti lakvinimodom |
| PT2467372T (pt) | 2009-08-10 | 2016-08-23 | Teva Pharma | Tratamento de distúrbios relacionados com bdnf usando laquinimod |
| CN102791130B (zh) | 2010-03-03 | 2015-02-25 | 泰华制药工业有限公司 | 使用拉喹莫德治疗狼疮肾炎 |
| JP5819328B2 (ja) | 2010-03-03 | 2015-11-24 | テバ ファーマシューティカル インダストリーズ リミティド | ラキニモドとメトトレキセートとの組合せによる関節リウマチの治療 |
| NZ602512A (en) | 2010-03-03 | 2014-07-25 | Teva Pharma | Treatment of lupus arthritis using laquinimod |
| SG10201505236YA (en) | 2010-07-09 | 2015-08-28 | Teva Pharma | Deuterated n-ethyl-n-phenyl-1,2-dihydro-4-hydroxy-5-chloro-1-methyl-2-oxoquinoline-3-carboxamide, salts and uses thereof |
| EP3056205A1 (en) | 2010-07-09 | 2016-08-17 | Teva Pharmaceutical Industries, Ltd. | 5-chloro-4-hydroxy-1-methyl-2-oxo-n-phenyl-1,2-dihydroquinoline-3-carboxamide, salts and uses thereof |
| WO2012078591A1 (en) | 2010-12-07 | 2012-06-14 | Teva Pharmaceutical Industries Ltd. | Use of laquinimod for reducing fatigue, improving functional status, and improving quality of life in multiple sclerosis patients |
| EA201490377A1 (ru) | 2011-07-28 | 2014-11-28 | Тева Фармасьютикал Индастриз Лтд. | Лечение рассеянного склероза комбинацией лаквинимода и глатирамера ацетата |
| WO2013016686A1 (en) | 2011-07-28 | 2013-01-31 | Teva Pharmaceutical Industries Ltd. | Treatment of multiple sclerosis with combination of laquinimod and interferon-beta |
| CN106344576A (zh) | 2011-10-12 | 2017-01-25 | 泰华制药工业有限公司 | 以拉喹莫德和芬戈莫德的组合治疗多发性硬化症 |
| CN106063787A (zh) | 2012-02-03 | 2016-11-02 | 泰华制药工业有限公司 | 拉喹莫德用于治疗一线抗TNFα疗法失败的克罗恩氏病患者的用途 |
| US20130259856A1 (en) | 2012-03-27 | 2013-10-03 | Teva Pharmaceutical Industries, Ltd. | Treatment of multiple sclerosis with combination of laquinimod and dimethyl fumarate |
| TW201804997A (zh) | 2012-05-02 | 2018-02-16 | 以色列商泰瓦藥品工業有限公司 | 高劑量拉喹莫德(laquinimod)於治療多發性硬化症之用途 |
| TW201350467A (zh) | 2012-05-08 | 2013-12-16 | Teva Pharma | Ｎ－乙基－４－羥基－１－甲基－５－（甲基（２，３，４，５，６－五羥基己基）胺基）－２－側氧－ｎ－苯基－１，２－二氫喹啉－３－甲醯胺 |
| US20130345257A1 (en) | 2012-06-26 | 2013-12-26 | The Regents Of The University Of California | Composition for lupus nephritis and methods of making and using the same |
| UY34896A (es) | 2012-07-12 | 2014-02-28 | Teva Pharma | Tratamiento de la esclerosis múltiple con una combinación de laquinimod y fampridina |
| TW201410244A (zh) | 2012-08-13 | 2014-03-16 | Teva Pharma | 用於治療ｇａｂａ媒介之疾病之拉喹莫德（ｌａｑｕｉｎｉｍｏｄ） |
| TW201410243A (zh) | 2012-08-13 | 2014-03-16 | Teva Pharma | 用於治療大麻素受體型１（ｃｂ１）媒介之疾病之拉喹莫德（ｌａｑｕｉｎｉｍｏｄ） |
| US20140107154A1 (en) | 2012-10-12 | 2014-04-17 | Teva Pharmaceutical Industries, Ltd. | Laquinimod for reducing thalamic damage in multiple sclerosis |
| JP2015535287A (ja) | 2012-11-07 | 2015-12-10 | テバ ファーマシューティカル インダストリーズ リミティド | ラキニモドのアミン塩 |
-
2013
- 2013-02-15 HK HK14111813.6A patent/HK1198296A1/xx unknown
- 2013-02-15 US US13/768,919 patent/US9284276B2/en active Active
- 2013-02-15 EA EA201491517A patent/EA201491517A1/ru unknown
- 2013-02-15 BR BR112014020372A patent/BR112014020372A8/pt active Search and Examination
- 2013-02-15 JP JP2014557840A patent/JP6215238B2/ja not_active Expired - Fee Related
- 2013-02-15 EP EP17158515.1A patent/EP3225617A1/en not_active Withdrawn
- 2013-02-15 EP EP13749429.0A patent/EP2744498A4/en not_active Withdrawn
- 2013-02-15 WO PCT/US2013/026476 patent/WO2013123419A1/en not_active Ceased
- 2013-02-15 CN CN201380009677.5A patent/CN104114172A/zh active Pending
- 2013-02-15 SG SG11201404419WA patent/SG11201404419WA/en unknown
- 2013-02-15 AU AU2013221304A patent/AU2013221304B2/en not_active Expired - Fee Related
- 2013-02-15 MX MX2014009889A patent/MX2014009889A/es unknown
- 2013-02-15 AR ARP130100481A patent/AR090073A1/es unknown
- 2013-02-15 CA CA2863409A patent/CA2863409A1/en not_active Abandoned
- 2013-02-15 KR KR1020147025755A patent/KR20140138725A/ko not_active Withdrawn
- 2013-02-18 TW TW102105618A patent/TW201339137A/zh unknown
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2014
- 2014-07-08 IL IL233556A patent/IL233556A0/en unknown
- 2014-09-04 ZA ZA2014/06492A patent/ZA201406492B/en unknown
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2016
- 2016-02-02 US US15/013,586 patent/US20160151345A1/en not_active Abandoned
- 2016-02-02 US US15/013,633 patent/US20160151346A1/en not_active Abandoned
- 2016-11-17 US US15/354,836 patent/US20170065576A1/en not_active Abandoned
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2017
- 2017-07-14 JP JP2017138167A patent/JP2018008965A/ja not_active Withdrawn
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