JP2013536857A5 - - Google Patents
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- Publication number
- JP2013536857A5 JP2013536857A5 JP2013527255A JP2013527255A JP2013536857A5 JP 2013536857 A5 JP2013536857 A5 JP 2013536857A5 JP 2013527255 A JP2013527255 A JP 2013527255A JP 2013527255 A JP2013527255 A JP 2013527255A JP 2013536857 A5 JP2013536857 A5 JP 2013536857A5
- Authority
- JP
- Japan
- Prior art keywords
- dosage form
- tetrahydro
- chloro
- methyl
- benzazepine
- 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
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- 239000002552 dosage form Substances 0.000 claims description 73
- 238000000034 method Methods 0.000 claims description 69
- 150000003839 salts Chemical class 0.000 claims description 69
- 239000008194 pharmaceutical composition Substances 0.000 claims description 33
- 230000037221 weight management Effects 0.000 claims description 33
- XTTZERNUQAFMOF-QMMMGPOBSA-N lorcaserin Chemical compound C[C@H]1CNCCC2=CC=C(Cl)C=C12 XTTZERNUQAFMOF-QMMMGPOBSA-N 0.000 claims description 31
- 239000012453 solvate Substances 0.000 claims description 19
- 239000007888 film coating Substances 0.000 claims description 16
- 238000009501 film coating Methods 0.000 claims description 16
- 150000004677 hydrates Chemical class 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 12
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 12
- 235000012054 meals Nutrition 0.000 claims description 12
- VOJUXHHACRXLTD-UHFFFAOYSA-N 1,4-dihydroxy-2-naphthoic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)O)=CC(O)=C21 VOJUXHHACRXLTD-UHFFFAOYSA-N 0.000 claims description 11
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 11
- 235000012631 food intake Nutrition 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 206010033307 Overweight Diseases 0.000 claims description 8
- 239000000883 anti-obesity agent Substances 0.000 claims description 8
- 229940125708 antidiabetic agent Drugs 0.000 claims description 8
- 239000003472 antidiabetic agent Substances 0.000 claims description 8
- 229940125710 antiobesity agent Drugs 0.000 claims description 8
- 230000004580 weight loss Effects 0.000 claims description 7
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 6
- 229930195725 Mannitol Natural products 0.000 claims description 6
- 229920000168 Microcrystalline cellulose Polymers 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 230000037406 food intake Effects 0.000 claims description 6
- 235000019359 magnesium stearate Nutrition 0.000 claims description 6
- 239000000594 mannitol Substances 0.000 claims description 6
- 235000010355 mannitol Nutrition 0.000 claims description 6
- 239000008108 microcrystalline cellulose Substances 0.000 claims description 6
- 235000019813 microcrystalline cellulose Nutrition 0.000 claims description 6
- 229940016286 microcrystalline cellulose Drugs 0.000 claims description 6
- 230000036186 satiety Effects 0.000 claims description 6
- 235000019627 satiety Nutrition 0.000 claims description 6
- KBRBOQRSMDBFNF-MABWYXAVSA-N (5r)-7-chloro-5-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine;(e)-3-phenylprop-2-enoic acid Chemical compound OC(=O)\C=C\C1=CC=CC=C1.C[C@H]1CNCCC2=CC=C(Cl)C=C12 KBRBOQRSMDBFNF-MABWYXAVSA-N 0.000 claims description 5
- PSWJLTWGTOAZAY-QRPNPIFTSA-N (5r)-7-chloro-5-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine;2-hydroxy-2-phenylacetic acid Chemical compound OC(=O)C(O)C1=CC=CC=C1.C[C@H]1CNCCC2=CC=C(Cl)C=C12 PSWJLTWGTOAZAY-QRPNPIFTSA-N 0.000 claims description 5
- NKBLAKRCFQQYPG-QRPNPIFTSA-N (5r)-7-chloro-5-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine;hydroiodide Chemical compound I.C[C@H]1CNCCC2=CC=C(Cl)C=C12 NKBLAKRCFQQYPG-QRPNPIFTSA-N 0.000 claims description 5
- FJTNYFLNJZFMAL-LOOJJACZSA-N (e)-but-2-enedioic acid;(5r)-7-chloro-5-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound OC(=O)\C=C\C(O)=O.C[C@H]1CNCCC2=CC=C(Cl)C=C12 FJTNYFLNJZFMAL-LOOJJACZSA-N 0.000 claims description 5
- FJTNYFLNJZFMAL-KZDSSNOQSA-N (z)-but-2-enedioic acid;(5r)-7-chloro-5-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound OC(=O)\C=C/C(O)=O.C[C@H]1CNCCC2=CC=C(Cl)C=C12 FJTNYFLNJZFMAL-KZDSSNOQSA-N 0.000 claims description 5
- KIKNVEPHVFMBHM-JZGIKJSDSA-N C(C1=CC=CC=C1)(=O)O.CC(=O)NC(=O)C.ClC=1C=CC2=C([C@H](CNCC2)C)C1 Chemical compound C(C1=CC=CC=C1)(=O)O.CC(=O)NC(=O)C.ClC=1C=CC2=C([C@H](CNCC2)C)C1 KIKNVEPHVFMBHM-JZGIKJSDSA-N 0.000 claims description 5
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 4
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 4
- 208000002705 Glucose Intolerance Diseases 0.000 claims description 4
- 206010020772 Hypertension Diseases 0.000 claims description 4
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 4
- 241001465754 Metazoa Species 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 235000013305 food Nutrition 0.000 claims description 4
- 235000003642 hunger Nutrition 0.000 claims description 4
- ITIHHRMYZPNGRC-QRPNPIFTSA-N lorcaserin hydrochloride Chemical compound Cl.C[C@H]1CNCCC2=CC=C(Cl)C=C12 ITIHHRMYZPNGRC-QRPNPIFTSA-N 0.000 claims description 4
- WRZCAWKMTLRWPR-VSODYHHCSA-N lorcaserin hydrochloride hemihydrate Chemical group O.Cl.Cl.C[C@H]1CNCCC2=CC=C(Cl)C=C12.C[C@H]1CNCCC2=CC=C(Cl)C=C12 WRZCAWKMTLRWPR-VSODYHHCSA-N 0.000 claims description 4
- 230000036470 plasma concentration Effects 0.000 claims description 4
- 201000002859 sleep apnea Diseases 0.000 claims description 4
- 238000002560 therapeutic procedure Methods 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000004615 ingredient Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 19
- 208000008589 Obesity Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 230000001939 inductive effect Effects 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 102000005962 receptors Human genes 0.000 claims 2
- 108020003175 receptors Proteins 0.000 claims 2
- OPWLNUCRCHHDDF-QRPNPIFTSA-N (5r)-7-chloro-5-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine;2,4-dioxo-1h-pyrimidine-6-carboxylic acid Chemical compound OC(=O)C1=CC(=O)NC(=O)N1.C[C@H]1CNCCC2=CC=C(Cl)C=C12 OPWLNUCRCHHDDF-QRPNPIFTSA-N 0.000 claims 1
- 206010018429 Glucose tolerance impaired Diseases 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- 239000012729 immediate-release (IR) formulation Substances 0.000 description 7
- DHHVAGZRUROJKS-UHFFFAOYSA-N phentermine Chemical compound CC(C)(N)CC1=CC=CC=C1 DHHVAGZRUROJKS-UHFFFAOYSA-N 0.000 description 6
- 239000001856 Ethyl cellulose Substances 0.000 description 5
- 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 description 5
- 229920001249 ethyl cellulose Polymers 0.000 description 5
- 235000019325 ethyl cellulose Nutrition 0.000 description 5
- ZCKAMNXUHHNZLN-UHFFFAOYSA-N Chlorphentermine Chemical group CC(C)(N)CC1=CC=C(Cl)C=C1 ZCKAMNXUHHNZLN-UHFFFAOYSA-N 0.000 description 3
- 229950007046 chlorphentermine Drugs 0.000 description 3
- HXCXASJHZQXCKK-UHFFFAOYSA-N clortermine Chemical compound CC(C)(N)CC1=CC=CC=C1Cl HXCXASJHZQXCKK-UHFFFAOYSA-N 0.000 description 3
- 229950000649 clortermine Drugs 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 238000007726 management method Methods 0.000 description 3
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical group CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 3
- 229960003105 metformin Drugs 0.000 description 3
- UMWAUEZOGHNSCH-UHFFFAOYSA-N pentorex Chemical compound CC(N)(C)C(C)C1=CC=CC=C1 UMWAUEZOGHNSCH-UHFFFAOYSA-N 0.000 description 3
- 229950000821 pentorex Drugs 0.000 description 3
- 229960003562 phentermine Drugs 0.000 description 3
- 201000009104 prediabetes syndrome Diseases 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- ZRPYKXHZFPGPRZ-UHFFFAOYSA-N 5-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound CC1CNCCC2=CC=CC=C12 ZRPYKXHZFPGPRZ-UHFFFAOYSA-N 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US40257810P | 2010-09-01 | 2010-09-01 | |
| US61/402,578 | 2010-09-01 | ||
| US40314310P | 2010-09-10 | 2010-09-10 | |
| US61/403,143 | 2010-09-10 | ||
| PCT/US2011/049914 WO2012030927A2 (en) | 2010-09-01 | 2011-08-31 | Modified-release dosage forms of 5-ht2c agonists useful for weight management |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016011493A Division JP2016056211A (ja) | 2010-09-01 | 2016-01-25 | 体重管理のために有用な５−ｈｔ２ｃアゴニストの改変放出剤形 |
| JP2017179402A Division JP2017214437A (ja) | 2010-09-01 | 2017-09-19 | 体重管理のために有用な５−ｈｔ２ｃアゴニストの改変放出剤形 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013536857A JP2013536857A (ja) | 2013-09-26 |
| JP2013536857A5 true JP2013536857A5 (https=) | 2014-10-16 |
| JP6272695B2 JP6272695B2 (ja) | 2018-01-31 |
Family
ID=44645820
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013527255A Expired - Fee Related JP6272695B2 (ja) | 2010-09-01 | 2011-08-31 | 体重管理のために有用な５−ｈｔ２ｃアゴニストの改変放出剤形 |
| JP2016011493A Pending JP2016056211A (ja) | 2010-09-01 | 2016-01-25 | 体重管理のために有用な５−ｈｔ２ｃアゴニストの改変放出剤形 |
| JP2017179402A Withdrawn JP2017214437A (ja) | 2010-09-01 | 2017-09-19 | 体重管理のために有用な５−ｈｔ２ｃアゴニストの改変放出剤形 |
| JP2019124572A Withdrawn JP2019163336A (ja) | 2010-09-01 | 2019-07-03 | 体重管理のために有用な５−ｈｔ２ｃアゴニストの改変放出剤形 |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016011493A Pending JP2016056211A (ja) | 2010-09-01 | 2016-01-25 | 体重管理のために有用な５−ｈｔ２ｃアゴニストの改変放出剤形 |
| JP2017179402A Withdrawn JP2017214437A (ja) | 2010-09-01 | 2017-09-19 | 体重管理のために有用な５−ｈｔ２ｃアゴニストの改変放出剤形 |
| JP2019124572A Withdrawn JP2019163336A (ja) | 2010-09-01 | 2019-07-03 | 体重管理のために有用な５−ｈｔ２ｃアゴニストの改変放出剤形 |
Country Status (11)
| Country | Link |
|---|---|
| US (3) | US20130315994A1 (https=) |
| EP (2) | EP3485878A1 (https=) |
| JP (4) | JP6272695B2 (https=) |
| KR (2) | KR20180118801A (https=) |
| CN (2) | CN107669687A (https=) |
| AU (1) | AU2011296003B2 (https=) |
| CA (2) | CA2808912C (https=) |
| ES (1) | ES2704455T3 (https=) |
| IL (1) | IL224829B (https=) |
| SG (2) | SG188362A1 (https=) |
| WO (1) | WO2012030927A2 (https=) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013536859A (ja) | 2010-09-01 | 2013-09-26 | アリーナ ファーマシューティカルズ， インコーポレイテッド | ５−ｈｔ２ｃアゴニストの非吸湿性塩 |
| KR20130138770A (ko) | 2010-09-01 | 2013-12-19 | 아레나 파마슈티칼스, 인크. | 광학적으로 활성 산을 갖는 로르카세린의 염 |
| KR20140091458A (ko) | 2010-09-01 | 2014-07-21 | 아레나 파마슈티칼스, 인크. | 신장 손상을 갖는 개체에 대한 로카세린의 투여 |
| EP3485878A1 (en) | 2010-09-01 | 2019-05-22 | Arena Pharmaceuticals, Inc. | Modified-release dosage forms of 5-ht2c agonists useful for weight management |
| US8399011B1 (en) * | 2012-08-10 | 2013-03-19 | Magnifica Inc. | Oral particle compositions containing a core and an acid-soluble coat |
| WO2014058441A1 (en) * | 2012-10-09 | 2014-04-17 | Arena Pharmaceuticals, Inc. | Method of weight management |
| US9549909B2 (en) | 2013-05-03 | 2017-01-24 | The Katholieke Universiteit Leuven | Method for the treatment of dravet syndrome |
| WO2015017423A2 (en) * | 2013-07-29 | 2015-02-05 | Aptalis Pharmatech, Inc. | Stabilized modified release folic acid derivative composition, its therapeutic use and methods of manufacture |
| EP2868656A1 (en) * | 2013-11-05 | 2015-05-06 | LEK Pharmaceuticals d.d. | Stabilized amorphous lorcaserin hydrochloride |
| EP2924024A3 (en) * | 2014-03-21 | 2016-01-20 | Medichem, S.A. | Solid forms of lorcaserin hydrochloride |
| WO2015161730A1 (zh) * | 2014-04-21 | 2015-10-29 | 杭州普晒医药科技有限公司 | 一种氯卡色林共晶及其制备方法、药物组合物和用途 |
| EA022748B1 (ru) * | 2014-06-02 | 2016-02-29 | Делкростон Менеджмент Лимитед | Способы получения двойных солей лоркасерина (варианты), продукты способов, двойные соли, фармацевтические композиции для лечения и/или профилактики нарушений, связанных с ожирением, их применение и способ лечения и/или профилактики нарушений, связанных с ожирением |
| KR102245345B1 (ko) * | 2014-09-29 | 2021-04-28 | 조게닉스 인터내셔널 리미티드 | 의약품 배포 제어를 위한 제어 시스템 |
| TW201618787A (zh) | 2014-10-30 | 2016-06-01 | 艾尼納製藥公司 | 組合物及方法 |
| WO2016151451A1 (en) * | 2015-03-24 | 2016-09-29 | Aurobindo Pharma Ltd | A process for the preparation of lorcaserin hydrochloride |
| WO2017112701A1 (en) | 2015-12-22 | 2017-06-29 | Zogenix International Limited | Metabolism resistant fenfluramine analogs and methods of using the same |
| PT4293009T (pt) | 2015-12-22 | 2025-09-08 | Zogenix International Ltd | Composições de fenfluramina e métodos de preparação das mesmas |
| WO2018035477A1 (en) * | 2016-08-19 | 2018-02-22 | Arena Pharmaceuticals, Inc. | 5-ht2c receptor agonists and compositions and methods of use |
| AU2017315273B2 (en) | 2016-08-24 | 2021-04-29 | Zogenix International Limited | Formulation for inhibiting formation of 5-HT 2B agonists and methods of using same |
| TWI820984B (zh) * | 2017-01-31 | 2023-11-01 | 美商基利科學股份有限公司 | 替諾福韋埃拉酚胺(tenofovir alafenamide)之晶型 |
| US10682317B2 (en) | 2017-09-26 | 2020-06-16 | Zogenix International Limited | Ketogenic diet compatible fenfluramine formulation |
| EP3733204A4 (en) | 2017-12-27 | 2021-09-15 | Takeda Pharmaceutical Company Limited | THERAPEUTIC AGENT FOR URINARY INCONTINENCE OF STRESS AND FECAL INCONTINENCE |
| EP3790537A1 (en) | 2018-05-11 | 2021-03-17 | Zogenix International Limited | Compositions and methods for treating seizure-induced sudden death |
| US11485734B2 (en) | 2018-10-02 | 2022-11-01 | Northwestern University | Beta-carbolines as positive allosteric modulators of the human serotonin receptor 2C (5-HT2C) |
| AU2019384963B2 (en) | 2018-11-19 | 2022-05-26 | Zogenix International Limited | Methods of treating Rett syndrome using fenfluramine |
| CN110354088A (zh) * | 2019-07-23 | 2019-10-22 | 南京昂谷医药科技有限公司 | 盐酸氯卡色林缓释片及其制备方法 |
| US11612574B2 (en) | 2020-07-17 | 2023-03-28 | Zogenix International Limited | Method of treating patients infected with severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) |
| CN113974568B (zh) * | 2021-11-09 | 2024-03-26 | 重庆火后草科技有限公司 | 基于斜率去干扰的睡眠过程的代谢率的计算方法 |
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-
2011
- 2011-08-31 EP EP18200702.1A patent/EP3485878A1/en not_active Withdrawn
- 2011-08-31 SG SG2013015599A patent/SG188362A1/en unknown
- 2011-08-31 CN CN201710915541.0A patent/CN107669687A/zh active Pending
- 2011-08-31 EP EP11755504.5A patent/EP2611427B1/en active Active
- 2011-08-31 SG SG10201506874UA patent/SG10201506874UA/en unknown
- 2011-08-31 US US13/820,107 patent/US20130315994A1/en not_active Abandoned
- 2011-08-31 CA CA2808912A patent/CA2808912C/en not_active Expired - Fee Related
- 2011-08-31 ES ES11755504T patent/ES2704455T3/es active Active
- 2011-08-31 CN CN2011800525606A patent/CN103189053A/zh active Pending
- 2011-08-31 WO PCT/US2011/049914 patent/WO2012030927A2/en not_active Ceased
- 2011-08-31 AU AU2011296003A patent/AU2011296003B2/en not_active Ceased
- 2011-08-31 KR KR1020187030466A patent/KR20180118801A/ko not_active Ceased
- 2011-08-31 KR KR1020137008319A patent/KR101913442B1/ko not_active Expired - Fee Related
- 2011-08-31 JP JP2013527255A patent/JP6272695B2/ja not_active Expired - Fee Related
- 2011-08-31 CA CA3050049A patent/CA3050049A1/en not_active Abandoned
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2013
- 2013-02-20 IL IL22482913A patent/IL224829B/en active IP Right Grant
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- 2016-01-25 JP JP2016011493A patent/JP2016056211A/ja active Pending
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- 2017-02-10 US US15/429,221 patent/US10226471B2/en active Active
- 2017-09-19 JP JP2017179402A patent/JP2017214437A/ja not_active Withdrawn
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- 2019-07-03 JP JP2019124572A patent/JP2019163336A/ja not_active Withdrawn
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